organic compounds
(1E,2E)-N1,N2-Bis(5′-methyl-[1,1′:3′,1′′-terphenyl]-4′-yl)acenaphthylene-1,2-diimine unknown solvent
aKey Laboratory of Bioelectrochemical and Environmental Analysis of Gansu Province, College of Chemistry & Chemical Engineering, Northwest Normal University, Lanzhou 730070, People's Republic of China
*Correspondence e-mail: zhaoyan2532@126.com
The title compound, C50H36N2, synthesized by the condensation reaction of 2-methyl-4,6-diphenylaniline and acenaphthylene-1,2-dione, crystallizes with two independent molecules (A and B) in the The two molecules differ essentially in the orientation of the phenyl ring at position 3′ of the terphenyl group with respect to the central ring of this unit. In molecule A this dihedral angle is 16.68 (14)°, while in molecule B the corresponding angle is 33.10 (16)°. The three-fused-ring 1,2-dihydroacenaphthylene units are planar in each molecule; r.m.s. deviation of 0.025 Å in molecule A and 0.017 Å in molecule B. The central rings of the terphenyl groups are almost normal to the mean plane of the three-fused-ring units with dihedral angles of 79.43 (12) and 82.66 (13)° in molecule A and 88.99 (13) and 87.98 (12)° in molecule B. In the crystal, the two molecules are linked via a C—H⋯N hydrogen bond. These A–B units are linked by a pair of C—H⋯π interactions, forming a four-molecule unit located about an inversion center. These four-molecule units are linked by weak π–π interactions [most significant intercentroid distance = 3.794 (2) Å], forming columns along direction [010]. A region of disordered electron density was corrected for using the SQUEEZE routine in PLATON [Spek (2015). Acta Cryst. C71, 9–18]. The formula mass and unit-cell characteristics of this unknown solvent were not be taken into account during the refinement.
Keywords: crystal structure; acenaphthylene-1,2-dione; α-diimine catalyst; potential bidentate ligand; C—H⋯N hydrogen bonding; π-π interactions.
CCDC reference: 1473249
Structure description
In the past few decades, there has been a rapid development of a series of α-diimine palladium and nickel complex catalysts [MX2(α-diimine)] (where M = Ni, Pd; X = halide) for the polymerization of α-olefins since the original discovery of highly active α-diimine nickel catalysts (Johnson et al., 1995). The and properties of the resulting polymers are greatly dependent on the reaction conditions (Helldörfer et al., 2003) and ligand structures (Meinhard et al., 2007; Popeney et al., 2011; Yuan et al., 2005; 2013). Nickel and palladium metal complex catalysts have a high for ethylene polymerization which gives high branched polyethylene, and the of ethylene and polar monomers have also high In this study, we describe the synthesis and of the title compound, a new potential bidentate ligand prepared by the condensation reaction of 2-methyl-4,6-diphenylaniline (1) and acenaphthylene-1,2-dione (2); Fig. 1.
The title compound crystallizes with two independent molecules in the A is illustrated in Fig. 2, while that of molecule B is illustrated in Fig. 3. The AutoMolFit of molecule B inverted on molecule A gives the best fit (Fig. 4; Spek, 2009). The two molecules having weighted and unit weight r.m.s. fits of 0.317 and 0.278 Å, respectively, for the 52 non-H atoms. The two molecules differ essentially in the orientation of the phenyl ring at position 3′ of the terphenyl group with respect to the central ring of this unit. In molecule A this dihedral angle (C7–C12/C1-C6) is 16.68 (14)°, while in molecule B the corresponding angle (C94–C99/C82–C87) is 33.10 (16)°. The three-fused-ring 1,2-dihydroacenaphthylene units (C20–C31 in molecule A, and C70–C81 in molecule B) are planar in each molecule with r.m.s. deviation of 0.025 Å in molecule A and 0.017 Å in molecule B. The central ring of the terphenyl groups (C1–C6 and C32–C37 in molecule A, and C82–C88 and C51–C56 in molecule B) are almost normal to the mean plane of the three-fused-ring units, with dihedral angles of 79.43 (12) and 82.66 (13)°, respectively, in molecule A, and 88.99 (13) and 87.98 (12)°, respectively, in molecule B.
The molecular structure of moleculeIn the crystal, the two molecules are linked via a C—H⋯N hydrogen bond (Table 1 and Fig. 5). These A–B units are linked about a center of inversion by a pair of C—H⋯π interactions, forming a four-molecule unit (Table 1 and Fig. 5). These four-molecule units are linked by slipped parallel π–π interactions forming columns along the b-axis direction [Cg3⋯ Cg18i = 3.794 (2) Å, interplanar distance = 3.590 (1) Å, slippage = 0.787 Å, Cg3 is the centroid of ring C7–C12 in molecule A and Cg18 is the centroid of ring C71–C75/C80 in molecule B, symmetry code (i): − x + 1, − y + 2, − z + 1].
Synthesis and crystallization
The synthesis of the title compound is illustrated in Fig. 1.
Synthesis of 2-methyl-4,6-diphenylaniline (1): 2-methyl-4,6-dibromo-aniline (2 mmol, 0.53 g) was dissolved in PEG-400 (10 ml) containing phenylboronic acid (0.586 g, 4.8 mmol), K2CO3 (0,828 g;0.6 mmol) PdCl2 (50 µg). The solution was placed in a round-bottomed flask and stirred at room temperature for 12 h. After the reaction, the solution was eluted with ethyl acetate/petroleum ether (v/v = 1:15) through a column, giving compound (1) as a colourless liquid (yield: 0.75 g, 79%).
Synthesis of the title compound: Formic acid (0.5 ml) was added to a stirred solution of acenaphthylene-1,2-dione (2) [0.18 g, 1.00 mmol] and compound (1) [0.57 g, 2.2 mmol) in ethanol (10 ml]. The mixture was refluxed for 24 h, and then cooled and the precipitate separated by filtration. The solid was recrystallized from EtOH/CH2Cl2 (v/v = 10:1), washed and dried under vacuum (yield: 0.43 g, 72%). Crystals suitable for X–ray structure analysis were grown from a cyclohexane/dichloromethane (v/v = 1:2) solution by slow evaporation.
Refinement
Crystal data, data collection and structure . A region of disordered electron density was corrected for using the SQUEEZE routine in PLATON (Spek, 2015): volume ca 690 Å3 for two regions of 36 and 65 electron counts. The formula mass and unit-cell characteristics of this unknown solvent were not taken into account during the refinement.
details are summarized in Table 2Structural data
CCDC reference: 1473249
10.1107/S2414314616005940/su4029sup1.cif
contains datablocks I, Global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2414314616005940/su4029Isup2.hkl
The synthesis of the title compound is illustrated in Fig. 1.
Synthesis of 2-methyl-4,6-diphenylaniline (1): 2-methyl-4,6-dibromo-aniline (2 mmol, 0.53 g) was dissolved in PEG-400 (10 ml) containing phenylboronic acid (0.586 g, 4.8 mmol), K2CO3 (0,828 g;0.6 mmol) PdCl2 (50 µg). The solution was placed in a round-bottomed flask and stirred at room temperature for 12 h. After the reaction, the solution was eluted with ethyl acetate/petroleum ether (v/v = 1:15) through a column, giving compound (1) as a colourless liquid (yield: 0.75 g, 79%).
Synthesis of the title compound: Formic acid (0.5 ml) was added to a stirred solution of acenaphthylene-1,2-dione (2) [0.18 g, 1.00 mmol] and compound (1) [0.57 g, 2.2 mmol) in ethanol (10 ml]. The mixture was refluxed for 24 h, and then cooled and the precipitate separated by filtration. The solid was recrystallized from EtOH/CH2Cl2 (v/v = 10:1), washed and dried under vacuum (yield: 0.43 g, 72%). Crystals suitable for X–ray structure analysis were grown from a cyclohexane/dichloromethane (v/v = 1:2) solution by slow evaporation.
Crystal data, data collection and structure
details are summarized in Table 2. A region of disordered electron density was corrected for using the SQUEEZE routine in PLATON (Spek, 2015): volume ca 690 Å3 for two regions of 36 and 65 electron counts. The formula mass and unit-cell characteristics of this unknown solvent were not taken into account during the refinement.In the past few decades, there has been a rapid development of a series of α-diimine palladium and nickel complex catalysts [MX2(α-diimine)] (where M = Ni, Pd; X = halide) for the polymerization of α-olefins since the original discovery of highly active α-diimine nickel catalysts (Johnson et al., 1995). The and properties of the resulting polymers are greatly dependent on the reaction conditions (Helldörfer et al., 2003) and ligand structures (Meinhard et al., 2007; Popeney et al., 2011; Yuan et al., 2005; 2013). Nickel and palladium metal complex catalysts have a high for ethylene polymerization which gives high branched polyethylene, and the of ethylene and polar monomers have also high In this study, we describe the synthesis and of the title compound, a new potential bidentate ligand prepared by the condensation reaction of 2-methyl-4,6-diphenylaniline (1) and acenaphthylene-1,2-dione (2); Fig. 1.
The title compound crystallizes with two independent molecules in the
The molecular structure of molecule A is illustrated in Fig. 2, while that of molecule B is illustrated in Fig. 3. The AutoMolFit of molecule B inverted on molecule A gives the best fit (Fig. 4; Spek, 2009). The two molecules having weighted and unit weight r.m.s. fits of 0.317 and 0.278 Å, respectively, for the 52 non-H atoms. The two molecules differ essentially in the orientation of the phenyl ring at position 3' of the terphenyl group with respect to the central ring of this unit. In molecule A this dihedral angle (C7–C12/C1-C6) is 16.68 (14)°, while in molecule B the corresponding angle (C94–C99/C82–C87) is 33.10 (16)°. The three-fused-ring 1,2-dihydroacenaphthylene units (C20–C31 in molecule A, and C70–C81 in molecule B) are planar in each molecule with r.m.s. deviation of 0.025 Å in molecule A and 0.017 Å in molecule B. The central ring of the terphenyl groups (C1–C6 and C32–C37 in molecule A, and C82–C88 and C51–C56 in molecule B) are almost normal to the mean plane of the three-fused-ring units, with dihedral angles of 79.43 (12) and 82.66 (13)°, respectively, in molecule A, and 88.99 (13) and 87.98 (12)°, respectively, in molecule B.In the crystal, the two molecules are linked via a C—H···N hydrogen bond (Table 1 and Fig. 5). These A–B units are linked about a center of inversion by a pair of C—H···π interactions, forming a four-molecule unit (Table 1 and Fig. 5). These four-molecule units are linked by slipped parallel π–π interactions forming columns along the b-axis direction [Cg3··· Cg18i = 3.794 (2) Å, interplanar distance = 3.590 (1) Å, slippage = 0.787 Å, Cg3 is the centroid of ring C7–C12 in molecule A and Cg18 is the centroid of ring C71–C75/C80 in molecule B, symmetry code (i): - x + 1, - y + 2, - z + 1].
Data collection: APEX2 (Bruker, 2008); cell
SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).Fig. 1. The condensation reaction of 2-methyl-4,6-diphenylaniline (1) and acenaphthylene-1,2-dione (2), giving the title compound. | |
Fig. 2. The molecular structure of molecule A of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level. | |
Fig. 3. The molecular structure of molecule B of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level. | |
Fig. 4. The AutoMolFit of molecule B (red) inverted on molecule A (black) gives the best fit (PLATON; Spek, 2009). | |
Fig. 5. A view along the c axis of the crystal packing of the title compound. The C—H···N hydrogen bonds and C—H···π interactions are represented by dashed lines (see Table 1). H atoms not involved in these interactions have been omitted for clarity. |
C50H36N2 | Z = 4 |
Mr = 664.81 | F(000) = 1400 |
Triclinic, P1 | Dx = 1.066 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 15.579 (3) Å | Cell parameters from 3879 reflections |
b = 16.799 (4) Å | θ = 2.3–21.0° |
c = 17.332 (4) Å | µ = 0.06 mm−1 |
α = 72.622 (2)° | T = 296 K |
β = 73.116 (2)° | Block, colorless |
γ = 84.324 (2)° | 0.23 × 0.21 × 0.16 mm |
V = 4142.0 (15) Å3 |
Bruker APEXII CCD diffractometer | 14707 independent reflections |
Radiation source: fine-focus sealed tube | 5868 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.041 |
φ and ω scans | θmax = 25.2°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | h = −18→18 |
Tmin = 0.986, Tmax = 0.990 | k = −20→20 |
29357 measured reflections | l = −20→20 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.065 | H-atom parameters constrained |
wR(F2) = 0.144 | w = 1/[σ2(Fo2) + (0.040P)2 + 0.3174P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.001 |
14707 reflections | Δρmax = 0.24 e Å−3 |
930 parameters | Δρmin = −0.29 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0017 (2) |
C50H36N2 | γ = 84.324 (2)° |
Mr = 664.81 | V = 4142.0 (15) Å3 |
Triclinic, P1 | Z = 4 |
a = 15.579 (3) Å | Mo Kα radiation |
b = 16.799 (4) Å | µ = 0.06 mm−1 |
c = 17.332 (4) Å | T = 296 K |
α = 72.622 (2)° | 0.23 × 0.21 × 0.16 mm |
β = 73.116 (2)° |
Bruker APEXII CCD diffractometer | 14707 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | 5868 reflections with I > 2σ(I) |
Tmin = 0.986, Tmax = 0.990 | Rint = 0.041 |
29357 measured reflections |
R[F2 > 2σ(F2)] = 0.065 | 0 restraints |
wR(F2) = 0.144 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.24 e Å−3 |
14707 reflections | Δρmin = −0.29 e Å−3 |
930 parameters |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
C7 | 0.31195 (15) | 0.84290 (16) | 0.84423 (15) | 0.0510 (8) | |
C8 | 0.34685 (16) | 0.92224 (15) | 0.82139 (13) | 0.0807 (11) | |
H8 | 0.3571 | 0.9556 | 0.7661 | 0.097* | |
C9 | 0.36642 (16) | 0.95177 (14) | 0.8812 (2) | 0.0916 (13) | |
H9 | 0.3898 | 1.0049 | 0.8659 | 0.110* | |
C10 | 0.35108 (18) | 0.9020 (2) | 0.96375 (17) | 0.0931 (14) | |
H10 | 0.3642 | 0.9217 | 1.0037 | 0.112* | |
C11 | 0.3162 (2) | 0.82262 (19) | 0.98659 (12) | 0.1235 (18) | |
H11 | 0.3059 | 0.7893 | 1.0419 | 0.148* | |
C12 | 0.29661 (18) | 0.79309 (13) | 0.92683 (18) | 0.0998 (14) | |
H12 | 0.2733 | 0.7400 | 0.9421 | 0.120* | |
C1 | 0.26934 (19) | 0.7493 (2) | 0.65182 (19) | 0.0488 (8) | |
C2 | 0.2781 (2) | 0.8342 (2) | 0.6375 (2) | 0.0611 (9) | |
C3 | 0.2890 (2) | 0.8636 (2) | 0.7015 (2) | 0.0630 (10) | |
H3 | 0.2928 | 0.9208 | 0.6922 | 0.076* | |
C4 | 0.29437 (19) | 0.8097 (2) | 0.77868 (19) | 0.0521 (8) | |
C5 | 0.28410 (19) | 0.7258 (2) | 0.79027 (19) | 0.0534 (9) | |
H5 | 0.2872 | 0.6884 | 0.8413 | 0.064* | |
C6 | 0.26940 (19) | 0.6942 (2) | 0.72966 (19) | 0.0483 (8) | |
C13 | 0.2546 (2) | 0.6033 (2) | 0.74996 (19) | 0.0557 (9) | |
C14 | 0.3040 (2) | 0.5452 (2) | 0.7955 (2) | 0.0742 (11) | |
H14 | 0.3488 | 0.5632 | 0.8119 | 0.089* | |
C15 | 0.2878 (3) | 0.4594 (3) | 0.8174 (2) | 0.0891 (13) | |
H15 | 0.3204 | 0.4210 | 0.8492 | 0.107* | |
C16 | 0.2237 (4) | 0.4331 (3) | 0.7916 (3) | 0.0936 (14) | |
H16 | 0.2140 | 0.3763 | 0.8043 | 0.112* | |
C17 | 0.1739 (3) | 0.4891 (3) | 0.7474 (3) | 0.1001 (14) | |
H17 | 0.1293 | 0.4707 | 0.7312 | 0.120* | |
C18 | 0.1896 (3) | 0.5727 (3) | 0.7268 (2) | 0.0771 (11) | |
H18 | 0.1552 | 0.6102 | 0.6961 | 0.093* | |
C19 | 0.2785 (3) | 0.8948 (2) | 0.5528 (2) | 0.1027 (14) | |
H19A | 0.3331 | 0.8876 | 0.5119 | 0.154* | |
H19B | 0.2746 | 0.9509 | 0.5569 | 0.154* | |
H19C | 0.2282 | 0.8842 | 0.5361 | 0.154* | |
C20 | 0.3182 (2) | 0.68981 (18) | 0.54082 (19) | 0.0470 (8) | |
C21 | 0.4137 (2) | 0.67354 (19) | 0.5368 (2) | 0.0521 (8) | |
C22 | 0.4692 (2) | 0.6909 (2) | 0.5773 (2) | 0.0704 (10) | |
H22 | 0.4471 | 0.7172 | 0.6195 | 0.084* | |
C23 | 0.5600 (3) | 0.6685 (3) | 0.5545 (3) | 0.0869 (12) | |
H23 | 0.5978 | 0.6810 | 0.5819 | 0.104* | |
C24 | 0.5952 (3) | 0.6293 (2) | 0.4938 (3) | 0.0850 (12) | |
H24 | 0.6558 | 0.6148 | 0.4811 | 0.102* | |
C25 | 0.5400 (3) | 0.6105 (2) | 0.4502 (2) | 0.0668 (10) | |
C26 | 0.5655 (3) | 0.5709 (2) | 0.3845 (3) | 0.0845 (12) | |
H26 | 0.6245 | 0.5527 | 0.3673 | 0.101* | |
C27 | 0.5042 (3) | 0.5597 (2) | 0.3468 (2) | 0.0863 (12) | |
H27 | 0.5226 | 0.5331 | 0.3046 | 0.104* | |
C28 | 0.4146 (3) | 0.5862 (2) | 0.3686 (2) | 0.0707 (10) | |
H28 | 0.3746 | 0.5785 | 0.3408 | 0.085* | |
C29 | 0.3871 (2) | 0.62395 (19) | 0.4323 (2) | 0.0542 (9) | |
C30 | 0.4493 (2) | 0.63508 (18) | 0.4723 (2) | 0.0532 (8) | |
C31 | 0.3009 (2) | 0.65909 (18) | 0.47245 (18) | 0.0504 (8) | |
C32 | 0.2104 (2) | 0.6412 (2) | 0.3931 (2) | 0.0538 (9) | |
C33 | 0.2297 (2) | 0.6958 (2) | 0.3117 (2) | 0.0534 (9) | |
C34 | 0.2151 (2) | 0.6676 (2) | 0.2489 (2) | 0.0624 (9) | |
H34 | 0.2279 | 0.7033 | 0.1945 | 0.075* | |
C35 | 0.1830 (2) | 0.5901 (2) | 0.2629 (2) | 0.0639 (10) | |
C36 | 0.1594 (2) | 0.5397 (2) | 0.3458 (2) | 0.0689 (10) | |
H36 | 0.1341 | 0.4881 | 0.3574 | 0.083* | |
C37 | 0.1723 (2) | 0.5637 (2) | 0.4115 (2) | 0.0630 (10) | |
C38 | 0.2641 (2) | 0.7811 (2) | 0.2913 (2) | 0.0509 (8) | |
C39 | 0.2268 (2) | 0.8331 (2) | 0.3420 (2) | 0.0675 (10) | |
H39 | 0.1814 | 0.8135 | 0.3913 | 0.081* | |
C40 | 0.2569 (3) | 0.9140 (2) | 0.3193 (3) | 0.0781 (11) | |
H40 | 0.2316 | 0.9480 | 0.3539 | 0.094* | |
C41 | 0.3232 (3) | 0.9444 (2) | 0.2471 (3) | 0.0763 (11) | |
H41 | 0.3427 | 0.9989 | 0.2321 | 0.092* | |
C42 | 0.3601 (2) | 0.8938 (2) | 0.1975 (2) | 0.0729 (11) | |
H42 | 0.4052 | 0.9138 | 0.1481 | 0.088* | |
C43 | 0.3314 (2) | 0.8131 (2) | 0.2199 (2) | 0.0639 (10) | |
H43 | 0.3584 | 0.7792 | 0.1855 | 0.077* | |
C44 | 0.1732 (3) | 0.5603 (2) | 0.1918 (2) | 0.0604 (10) | |
C45 | 0.2328 (3) | 0.5863 (2) | 0.1142 (3) | 0.0896 (13) | |
H45 | 0.2776 | 0.6233 | 0.1055 | 0.108* | |
C46 | 0.2273 (4) | 0.5581 (3) | 0.0477 (3) | 0.1095 (16) | |
H46 | 0.2688 | 0.5753 | −0.0047 | 0.131* | |
C47 | 0.1602 (5) | 0.5047 (3) | 0.0605 (4) | 0.1186 (19) | |
H47 | 0.1555 | 0.4865 | 0.0162 | 0.142* | |
C48 | 0.0998 (4) | 0.4778 (3) | 0.1380 (4) | 0.1112 (17) | |
H48 | 0.0549 | 0.4407 | 0.1473 | 0.133* | |
C49 | 0.1077 (3) | 0.5081 (2) | 0.2038 (3) | 0.0855 (12) | |
H49 | 0.0665 | 0.4915 | 0.2564 | 0.103* | |
C50 | 0.1477 (3) | 0.5070 (2) | 0.4999 (2) | 0.0949 (13) | |
H50A | 0.2011 | 0.4901 | 0.5180 | 0.142* | |
H50B | 0.1183 | 0.4587 | 0.5016 | 0.142* | |
H50C | 0.1081 | 0.5361 | 0.5366 | 0.142* | |
C51 | 0.8308 (2) | 0.76630 (18) | 0.26840 (19) | 0.0506 (8) | |
C52 | 0.9136 (2) | 0.72957 (19) | 0.2736 (2) | 0.0539 (9) | |
C53 | 0.9371 (2) | 0.71489 (19) | 0.3476 (2) | 0.0591 (9) | |
H53 | 0.9926 | 0.6904 | 0.3509 | 0.071* | |
C54 | 0.8800 (2) | 0.73574 (19) | 0.4176 (2) | 0.0538 (9) | |
C55 | 0.7973 (2) | 0.77178 (18) | 0.41044 (19) | 0.0545 (9) | |
H55 | 0.7581 | 0.7857 | 0.4565 | 0.065* | |
C56 | 0.7713 (2) | 0.78774 (17) | 0.33696 (19) | 0.0471 (8) | |
C57 | 0.9076 (2) | 0.71895 (18) | 0.4972 (2) | 0.0527 (9) | |
C58 | 0.9928 (3) | 0.7233 (2) | 0.4962 (2) | 0.0766 (11) | |
H58 | 1.0368 | 0.7340 | 0.4451 | 0.092* | |
C59 | 1.0182 (3) | 0.7122 (2) | 0.5705 (3) | 0.0910 (13) | |
H59 | 1.0780 | 0.7163 | 0.5682 | 0.109* | |
C60 | 0.9536 (3) | 0.6954 (2) | 0.6464 (3) | 0.0825 (12) | |
H60 | 0.9693 | 0.6886 | 0.6959 | 0.099* | |
C61 | 0.8648 (3) | 0.6886 (2) | 0.6488 (2) | 0.0790 (11) | |
H61 | 0.8209 | 0.6760 | 0.7000 | 0.095* | |
C62 | 0.8416 (2) | 0.70062 (19) | 0.5749 (2) | 0.0664 (10) | |
H62 | 0.7819 | 0.6965 | 0.5766 | 0.080* | |
C63 | 0.6810 (2) | 0.8266 (2) | 0.33531 (19) | 0.0552 (9) | |
C64 | 0.6497 (3) | 0.8902 (2) | 0.3721 (2) | 0.0710 (10) | |
H64 | 0.6874 | 0.9114 | 0.3940 | 0.085* | |
C65 | 0.5653 (3) | 0.9229 (3) | 0.3773 (2) | 0.0985 (14) | |
H65 | 0.5464 | 0.9659 | 0.4020 | 0.118* | |
C66 | 0.5085 (3) | 0.8927 (4) | 0.3462 (3) | 0.1140 (18) | |
H66 | 0.4505 | 0.9142 | 0.3507 | 0.137* | |
C67 | 0.5375 (3) | 0.8304 (4) | 0.3084 (3) | 0.1068 (16) | |
H67 | 0.4994 | 0.8106 | 0.2860 | 0.128* | |
C68 | 0.6237 (3) | 0.7964 (2) | 0.3032 (2) | 0.0784 (11) | |
H68 | 0.6425 | 0.7535 | 0.2781 | 0.094* | |
C69 | 0.9770 (2) | 0.7041 (2) | 0.1997 (2) | 0.0746 (11) | |
H69A | 1.0356 | 0.6932 | 0.2084 | 0.112* | |
H69B | 0.9801 | 0.7484 | 0.1489 | 0.112* | |
H69C | 0.9552 | 0.6547 | 0.1952 | 0.112* | |
C70 | 0.81620 (19) | 0.8452 (2) | 0.13499 (19) | 0.0456 (8) | |
C71 | 0.8550 (2) | 0.92518 (18) | 0.12345 (19) | 0.0486 (8) | |
C72 | 0.8870 (2) | 0.9589 (2) | 0.1719 (2) | 0.0654 (10) | |
H72 | 0.8871 | 0.9283 | 0.2263 | 0.078* | |
C73 | 0.9201 (2) | 1.0411 (2) | 0.1382 (3) | 0.0797 (11) | |
H73 | 0.9414 | 1.0641 | 0.1715 | 0.096* | |
C74 | 0.9218 (3) | 1.0874 (2) | 0.0591 (3) | 0.0862 (12) | |
H74 | 0.9444 | 1.1411 | 0.0393 | 0.103* | |
C75 | 0.8898 (2) | 1.0551 (2) | 0.0065 (2) | 0.0670 (10) | |
C76 | 0.8858 (3) | 1.0956 (2) | −0.0769 (3) | 0.0879 (12) | |
H76 | 0.9072 | 1.1496 | −0.1029 | 0.105* | |
C77 | 0.8513 (3) | 1.0568 (3) | −0.1192 (2) | 0.0824 (12) | |
H77 | 0.8497 | 1.0851 | −0.1738 | 0.099* | |
C78 | 0.8178 (2) | 0.9754 (2) | −0.0835 (2) | 0.0629 (9) | |
H78 | 0.7947 | 0.9500 | −0.1139 | 0.075* | |
C79 | 0.82002 (19) | 0.93409 (19) | −0.0025 (2) | 0.0493 (8) | |
C80 | 0.8562 (2) | 0.9742 (2) | 0.0411 (2) | 0.0502 (8) | |
C81 | 0.79069 (19) | 0.8515 (2) | 0.05548 (18) | 0.0450 (8) | |
C82 | 0.7271 (2) | 0.80212 (19) | −0.02622 (19) | 0.0504 (8) | |
C83 | 0.7878 (2) | 0.77977 (18) | −0.09352 (19) | 0.0480 (8) | |
C84 | 0.7617 (2) | 0.79215 (18) | −0.16637 (19) | 0.0517 (8) | |
H84 | 0.8020 | 0.7784 | −0.2120 | 0.062* | |
C85 | 0.6780 (2) | 0.82414 (19) | −0.17419 (19) | 0.0520 (8) | |
C86 | 0.6187 (2) | 0.8422 (2) | −0.1044 (2) | 0.0616 (9) | |
H86 | 0.5614 | 0.8619 | −0.1073 | 0.074* | |
C87 | 0.6419 (2) | 0.8317 (2) | −0.0305 (2) | 0.0618 (9) | |
C88 | 0.8793 (2) | 0.7470 (2) | −0.0903 (2) | 0.0512 (8) | |
C89 | 0.8943 (2) | 0.6866 (2) | −0.0210 (2) | 0.0653 (10) | |
H89 | 0.8462 | 0.6673 | 0.0259 | 0.078* | |
C90 | 0.9794 (3) | 0.6543 (2) | −0.0199 (3) | 0.0821 (12) | |
H90 | 0.9881 | 0.6137 | 0.0272 | 0.099* | |
C91 | 1.0508 (3) | 0.6828 (3) | −0.0891 (3) | 0.0894 (13) | |
H91 | 1.1082 | 0.6617 | −0.0887 | 0.107* | |
C92 | 1.0378 (3) | 0.7421 (3) | −0.1585 (2) | 0.0778 (11) | |
H92 | 1.0859 | 0.7609 | −0.2056 | 0.093* | |
C93 | 0.9524 (3) | 0.7738 (2) | −0.1581 (2) | 0.0657 (10) | |
H93 | 0.9441 | 0.8147 | −0.2052 | 0.079* | |
C94 | 0.6529 (2) | 0.83902 (18) | −0.2551 (2) | 0.0498 (8) | |
C95 | 0.7146 (2) | 0.86355 (19) | −0.3299 (2) | 0.0637 (10) | |
H95 | 0.7736 | 0.8703 | −0.3313 | 0.076* | |
C96 | 0.6921 (3) | 0.8790 (2) | −0.4048 (2) | 0.0782 (11) | |
H96 | 0.7359 | 0.8949 | −0.4560 | 0.094* | |
C97 | 0.6048 (3) | 0.8706 (2) | −0.4028 (3) | 0.0884 (13) | |
H97 | 0.5888 | 0.8806 | −0.4525 | 0.106* | |
C98 | 0.5420 (3) | 0.8474 (2) | −0.3274 (3) | 0.0878 (12) | |
H98 | 0.4825 | 0.8423 | −0.3256 | 0.105* | |
C99 | 0.5658 (3) | 0.8315 (2) | −0.2534 (2) | 0.0717 (10) | |
H99 | 0.5224 | 0.8156 | −0.2020 | 0.086* | |
C100 | 0.5755 (2) | 0.8559 (3) | 0.0424 (2) | 0.0992 (14) | |
H10A | 0.5746 | 0.8131 | 0.0938 | 0.149* | |
H10B | 0.5168 | 0.8623 | 0.0338 | 0.149* | |
H10C | 0.5932 | 0.9076 | 0.0458 | 0.149* | |
N1 | 0.25457 (17) | 0.72250 (15) | 0.58708 (16) | 0.0530 (7) | |
N2 | 0.22359 (19) | 0.66608 (15) | 0.46041 (15) | 0.0557 (7) | |
N3 | 0.80571 (17) | 0.77649 (16) | 0.19320 (16) | 0.0552 (7) | |
N4 | 0.74955 (16) | 0.79299 (16) | 0.04974 (14) | 0.0514 (7) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C7 | 0.048 (2) | 0.060 (2) | 0.054 (2) | 0.0065 (18) | −0.0176 (18) | −0.0279 (19) |
C8 | 0.110 (3) | 0.089 (3) | 0.063 (3) | −0.006 (2) | −0.034 (2) | −0.040 (2) |
C9 | 0.116 (3) | 0.096 (3) | 0.084 (3) | −0.004 (3) | −0.035 (3) | −0.047 (3) |
C10 | 0.103 (3) | 0.122 (4) | 0.086 (3) | 0.032 (3) | −0.050 (3) | −0.063 (3) |
C11 | 0.217 (6) | 0.098 (4) | 0.073 (3) | −0.002 (4) | −0.063 (3) | −0.027 (3) |
C12 | 0.167 (4) | 0.083 (3) | 0.074 (3) | −0.003 (3) | −0.055 (3) | −0.036 (3) |
C1 | 0.053 (2) | 0.055 (2) | 0.042 (2) | 0.0005 (17) | −0.0165 (17) | −0.0169 (18) |
C2 | 0.080 (3) | 0.064 (3) | 0.050 (2) | 0.006 (2) | −0.034 (2) | −0.019 (2) |
C3 | 0.084 (3) | 0.048 (2) | 0.062 (2) | −0.0010 (19) | −0.028 (2) | −0.0161 (19) |
C4 | 0.052 (2) | 0.058 (2) | 0.049 (2) | 0.0044 (18) | −0.0151 (17) | −0.0205 (19) |
C5 | 0.057 (2) | 0.057 (2) | 0.041 (2) | 0.0026 (18) | −0.0085 (17) | −0.0130 (17) |
C6 | 0.050 (2) | 0.053 (2) | 0.046 (2) | −0.0001 (16) | −0.0105 (17) | −0.0227 (18) |
C13 | 0.063 (2) | 0.053 (2) | 0.047 (2) | −0.001 (2) | −0.0061 (19) | −0.0175 (18) |
C14 | 0.089 (3) | 0.063 (3) | 0.068 (3) | 0.004 (2) | −0.016 (2) | −0.021 (2) |
C15 | 0.116 (4) | 0.060 (3) | 0.072 (3) | 0.007 (3) | −0.006 (3) | −0.013 (2) |
C16 | 0.119 (4) | 0.066 (3) | 0.082 (3) | −0.030 (3) | 0.003 (3) | −0.022 (3) |
C17 | 0.108 (4) | 0.084 (4) | 0.103 (4) | −0.037 (3) | −0.015 (3) | −0.020 (3) |
C18 | 0.083 (3) | 0.071 (3) | 0.080 (3) | −0.018 (2) | −0.024 (2) | −0.019 (2) |
C19 | 0.179 (4) | 0.068 (3) | 0.073 (3) | −0.007 (3) | −0.059 (3) | −0.010 (2) |
C20 | 0.058 (2) | 0.042 (2) | 0.040 (2) | −0.0046 (17) | −0.0121 (18) | −0.0100 (16) |
C21 | 0.047 (2) | 0.058 (2) | 0.053 (2) | −0.0069 (17) | −0.0139 (18) | −0.0170 (18) |
C22 | 0.059 (3) | 0.085 (3) | 0.070 (3) | −0.005 (2) | −0.013 (2) | −0.030 (2) |
C23 | 0.063 (3) | 0.106 (3) | 0.097 (3) | −0.013 (2) | −0.025 (3) | −0.030 (3) |
C24 | 0.053 (3) | 0.095 (3) | 0.096 (3) | 0.000 (2) | −0.008 (3) | −0.023 (3) |
C25 | 0.060 (3) | 0.069 (3) | 0.063 (3) | 0.001 (2) | −0.008 (2) | −0.016 (2) |
C26 | 0.067 (3) | 0.086 (3) | 0.084 (3) | 0.015 (2) | 0.002 (2) | −0.027 (2) |
C27 | 0.082 (3) | 0.097 (3) | 0.078 (3) | 0.010 (3) | −0.002 (3) | −0.044 (2) |
C28 | 0.080 (3) | 0.074 (3) | 0.061 (2) | 0.007 (2) | −0.015 (2) | −0.030 (2) |
C29 | 0.061 (2) | 0.052 (2) | 0.048 (2) | −0.0013 (18) | −0.0097 (19) | −0.0166 (17) |
C30 | 0.055 (2) | 0.046 (2) | 0.052 (2) | −0.0002 (17) | −0.0056 (19) | −0.0113 (17) |
C31 | 0.065 (3) | 0.046 (2) | 0.038 (2) | −0.0045 (18) | −0.0092 (19) | −0.0123 (16) |
C32 | 0.064 (2) | 0.056 (2) | 0.057 (2) | 0.0057 (19) | −0.0253 (19) | −0.033 (2) |
C33 | 0.064 (2) | 0.054 (2) | 0.051 (2) | 0.0033 (18) | −0.0215 (19) | −0.0237 (19) |
C34 | 0.083 (3) | 0.058 (2) | 0.055 (2) | 0.001 (2) | −0.029 (2) | −0.0207 (19) |
C35 | 0.087 (3) | 0.049 (2) | 0.068 (3) | 0.001 (2) | −0.034 (2) | −0.021 (2) |
C36 | 0.094 (3) | 0.050 (2) | 0.077 (3) | −0.004 (2) | −0.036 (2) | −0.026 (2) |
C37 | 0.082 (3) | 0.056 (2) | 0.060 (3) | 0.001 (2) | −0.026 (2) | −0.023 (2) |
C38 | 0.057 (2) | 0.055 (2) | 0.049 (2) | 0.0020 (19) | −0.0208 (19) | −0.0228 (19) |
C39 | 0.076 (3) | 0.062 (3) | 0.065 (2) | −0.002 (2) | −0.013 (2) | −0.025 (2) |
C40 | 0.099 (3) | 0.064 (3) | 0.079 (3) | 0.001 (2) | −0.022 (3) | −0.034 (2) |
C41 | 0.104 (3) | 0.056 (3) | 0.072 (3) | −0.013 (2) | −0.029 (3) | −0.014 (2) |
C42 | 0.084 (3) | 0.073 (3) | 0.065 (3) | −0.013 (2) | −0.017 (2) | −0.022 (2) |
C43 | 0.074 (3) | 0.067 (3) | 0.062 (3) | −0.003 (2) | −0.021 (2) | −0.033 (2) |
C44 | 0.088 (3) | 0.048 (2) | 0.064 (3) | 0.001 (2) | −0.042 (2) | −0.025 (2) |
C45 | 0.138 (4) | 0.069 (3) | 0.080 (3) | −0.013 (3) | −0.043 (3) | −0.032 (3) |
C46 | 0.172 (5) | 0.089 (3) | 0.085 (3) | −0.016 (3) | −0.050 (3) | −0.033 (3) |
C47 | 0.214 (6) | 0.078 (4) | 0.102 (4) | 0.002 (4) | −0.097 (4) | −0.030 (3) |
C48 | 0.178 (5) | 0.075 (3) | 0.116 (4) | −0.013 (3) | −0.085 (4) | −0.030 (3) |
C49 | 0.117 (4) | 0.073 (3) | 0.084 (3) | 0.006 (3) | −0.051 (3) | −0.027 (2) |
C50 | 0.142 (4) | 0.073 (3) | 0.072 (3) | −0.027 (3) | −0.028 (3) | −0.018 (2) |
C51 | 0.067 (2) | 0.047 (2) | 0.043 (2) | −0.0067 (18) | −0.0208 (19) | −0.0126 (16) |
C52 | 0.066 (3) | 0.051 (2) | 0.047 (2) | −0.0028 (18) | −0.016 (2) | −0.0160 (17) |
C53 | 0.060 (2) | 0.064 (2) | 0.057 (2) | 0.0094 (18) | −0.024 (2) | −0.0199 (19) |
C54 | 0.060 (2) | 0.058 (2) | 0.048 (2) | 0.0054 (18) | −0.0225 (19) | −0.0172 (17) |
C55 | 0.060 (2) | 0.058 (2) | 0.047 (2) | −0.0003 (18) | −0.0162 (18) | −0.0149 (17) |
C56 | 0.058 (2) | 0.045 (2) | 0.040 (2) | −0.0047 (17) | −0.0185 (18) | −0.0086 (16) |
C57 | 0.063 (3) | 0.056 (2) | 0.046 (2) | 0.0036 (18) | −0.025 (2) | −0.0168 (17) |
C58 | 0.065 (3) | 0.111 (3) | 0.052 (2) | 0.004 (2) | −0.017 (2) | −0.023 (2) |
C59 | 0.077 (3) | 0.129 (4) | 0.078 (3) | 0.015 (3) | −0.034 (3) | −0.039 (3) |
C60 | 0.098 (3) | 0.097 (3) | 0.069 (3) | 0.023 (3) | −0.044 (3) | −0.036 (2) |
C61 | 0.097 (3) | 0.086 (3) | 0.056 (3) | 0.022 (2) | −0.026 (2) | −0.027 (2) |
C62 | 0.078 (3) | 0.072 (2) | 0.059 (3) | 0.017 (2) | −0.035 (2) | −0.023 (2) |
C63 | 0.059 (2) | 0.061 (2) | 0.044 (2) | −0.007 (2) | −0.0239 (19) | −0.0011 (18) |
C64 | 0.073 (3) | 0.075 (3) | 0.062 (2) | 0.018 (2) | −0.025 (2) | −0.015 (2) |
C65 | 0.098 (4) | 0.115 (4) | 0.076 (3) | 0.040 (3) | −0.037 (3) | −0.018 (3) |
C66 | 0.076 (4) | 0.166 (5) | 0.080 (4) | 0.022 (4) | −0.027 (3) | −0.009 (3) |
C67 | 0.071 (4) | 0.164 (5) | 0.080 (3) | −0.014 (3) | −0.039 (3) | −0.004 (3) |
C68 | 0.074 (3) | 0.092 (3) | 0.066 (3) | −0.010 (2) | −0.030 (2) | −0.005 (2) |
C69 | 0.080 (3) | 0.083 (3) | 0.064 (2) | 0.005 (2) | −0.018 (2) | −0.029 (2) |
C70 | 0.051 (2) | 0.045 (2) | 0.042 (2) | −0.0048 (17) | −0.0136 (17) | −0.0131 (17) |
C71 | 0.057 (2) | 0.043 (2) | 0.053 (2) | −0.0048 (17) | −0.0235 (18) | −0.0168 (18) |
C72 | 0.082 (3) | 0.063 (3) | 0.067 (2) | −0.005 (2) | −0.038 (2) | −0.023 (2) |
C73 | 0.101 (3) | 0.060 (3) | 0.101 (3) | −0.015 (2) | −0.054 (3) | −0.028 (2) |
C74 | 0.097 (3) | 0.054 (3) | 0.113 (4) | −0.016 (2) | −0.042 (3) | −0.013 (3) |
C75 | 0.071 (3) | 0.051 (2) | 0.080 (3) | −0.009 (2) | −0.029 (2) | −0.010 (2) |
C76 | 0.101 (3) | 0.063 (3) | 0.084 (3) | −0.025 (2) | −0.030 (3) | 0.013 (2) |
C77 | 0.094 (3) | 0.078 (3) | 0.066 (3) | −0.008 (2) | −0.028 (2) | 0.002 (2) |
C78 | 0.069 (3) | 0.064 (3) | 0.051 (2) | −0.003 (2) | −0.0188 (19) | −0.0078 (19) |
C79 | 0.051 (2) | 0.051 (2) | 0.046 (2) | −0.0044 (17) | −0.0161 (17) | −0.0109 (18) |
C80 | 0.050 (2) | 0.044 (2) | 0.055 (2) | −0.0045 (17) | −0.0164 (18) | −0.0079 (18) |
C81 | 0.044 (2) | 0.053 (2) | 0.044 (2) | −0.0024 (17) | −0.0110 (16) | −0.0239 (18) |
C82 | 0.051 (2) | 0.069 (2) | 0.040 (2) | −0.0087 (18) | −0.0155 (18) | −0.0228 (17) |
C83 | 0.053 (2) | 0.058 (2) | 0.043 (2) | −0.0071 (17) | −0.0157 (18) | −0.0230 (17) |
C84 | 0.052 (2) | 0.064 (2) | 0.043 (2) | −0.0032 (18) | −0.0102 (18) | −0.0237 (17) |
C85 | 0.053 (2) | 0.064 (2) | 0.048 (2) | −0.0019 (18) | −0.0176 (19) | −0.0242 (18) |
C86 | 0.050 (2) | 0.082 (3) | 0.059 (2) | 0.0000 (18) | −0.014 (2) | −0.031 (2) |
C87 | 0.058 (2) | 0.093 (3) | 0.046 (2) | −0.002 (2) | −0.0128 (19) | −0.037 (2) |
C88 | 0.058 (2) | 0.061 (2) | 0.044 (2) | −0.0061 (19) | −0.016 (2) | −0.0242 (18) |
C89 | 0.065 (3) | 0.072 (3) | 0.058 (2) | −0.002 (2) | −0.012 (2) | −0.022 (2) |
C90 | 0.087 (3) | 0.089 (3) | 0.077 (3) | 0.019 (3) | −0.039 (3) | −0.024 (2) |
C91 | 0.060 (3) | 0.118 (4) | 0.100 (4) | 0.017 (3) | −0.029 (3) | −0.044 (3) |
C92 | 0.059 (3) | 0.103 (3) | 0.069 (3) | 0.000 (2) | −0.015 (2) | −0.024 (2) |
C93 | 0.065 (3) | 0.080 (3) | 0.054 (2) | −0.001 (2) | −0.016 (2) | −0.023 (2) |
C94 | 0.049 (2) | 0.051 (2) | 0.051 (2) | −0.0012 (17) | −0.012 (2) | −0.0198 (17) |
C95 | 0.079 (3) | 0.066 (2) | 0.055 (2) | 0.000 (2) | −0.028 (2) | −0.0213 (19) |
C96 | 0.101 (4) | 0.080 (3) | 0.051 (3) | 0.005 (2) | −0.021 (2) | −0.017 (2) |
C97 | 0.108 (4) | 0.107 (3) | 0.066 (3) | 0.028 (3) | −0.047 (3) | −0.035 (3) |
C98 | 0.083 (3) | 0.124 (4) | 0.072 (3) | 0.015 (3) | −0.037 (3) | −0.041 (3) |
C99 | 0.076 (3) | 0.091 (3) | 0.061 (3) | 0.003 (2) | −0.026 (2) | −0.034 (2) |
C100 | 0.070 (3) | 0.177 (4) | 0.075 (3) | 0.016 (3) | −0.022 (2) | −0.075 (3) |
N1 | 0.0632 (19) | 0.0567 (18) | 0.0465 (17) | 0.0013 (14) | −0.0177 (15) | −0.0238 (14) |
N2 | 0.061 (2) | 0.0595 (18) | 0.0519 (18) | −0.0010 (15) | −0.0178 (16) | −0.0212 (14) |
N3 | 0.072 (2) | 0.0536 (19) | 0.0468 (18) | −0.0049 (15) | −0.0221 (15) | −0.0173 (15) |
N4 | 0.0555 (18) | 0.0631 (19) | 0.0427 (17) | −0.0100 (14) | −0.0117 (14) | −0.0243 (14) |
C7—C8 | 1.3900 | C51—C52 | 1.389 (4) |
C7—C12 | 1.3900 | C51—C56 | 1.397 (4) |
C7—C4 | 1.505 (3) | C51—N3 | 1.425 (3) |
C8—C9 | 1.3900 | C52—C53 | 1.380 (4) |
C8—H8 | 0.9300 | C52—C69 | 1.518 (4) |
C9—C10 | 1.3900 | C53—C54 | 1.397 (4) |
C9—H9 | 0.9300 | C53—H53 | 0.9300 |
C10—C11 | 1.3900 | C54—C55 | 1.391 (4) |
C10—H10 | 0.9300 | C54—C57 | 1.503 (4) |
C11—C12 | 1.3900 | C55—C56 | 1.390 (4) |
C11—H11 | 0.9300 | C55—H55 | 0.9300 |
C12—H12 | 0.9300 | C56—C63 | 1.495 (4) |
C1—C2 | 1.386 (4) | C57—C58 | 1.331 (4) |
C1—C6 | 1.390 (4) | C57—C62 | 1.406 (4) |
C1—N1 | 1.410 (3) | C58—C59 | 1.410 (4) |
C2—C3 | 1.397 (4) | C58—H58 | 0.9300 |
C2—C19 | 1.514 (4) | C59—C60 | 1.374 (5) |
C3—C4 | 1.394 (4) | C59—H59 | 0.9300 |
C3—H3 | 0.9300 | C60—C61 | 1.387 (5) |
C4—C5 | 1.383 (4) | C60—H60 | 0.9300 |
C5—C6 | 1.390 (4) | C61—C62 | 1.383 (4) |
C5—H5 | 0.9300 | C61—H61 | 0.9300 |
C6—C13 | 1.486 (4) | C62—H62 | 0.9300 |
C13—C14 | 1.384 (4) | C63—C64 | 1.382 (4) |
C13—C18 | 1.384 (4) | C63—C68 | 1.383 (4) |
C14—C15 | 1.405 (5) | C64—C65 | 1.363 (5) |
C14—H14 | 0.9300 | C64—H64 | 0.9300 |
C15—C16 | 1.363 (5) | C65—C66 | 1.363 (5) |
C15—H15 | 0.9300 | C65—H65 | 0.9300 |
C16—C17 | 1.357 (5) | C66—C67 | 1.368 (6) |
C16—H16 | 0.9300 | C66—H66 | 0.9300 |
C17—C18 | 1.370 (5) | C67—C68 | 1.395 (5) |
C17—H17 | 0.9300 | C67—H67 | 0.9300 |
C18—H18 | 0.9300 | C68—H68 | 0.9300 |
C19—H19A | 0.9600 | C69—H69A | 0.9600 |
C19—H19B | 0.9600 | C69—H69B | 0.9600 |
C19—H19C | 0.9600 | C69—H69C | 0.9600 |
C20—N1 | 1.273 (3) | C70—N3 | 1.274 (3) |
C20—C21 | 1.472 (4) | C70—C71 | 1.463 (4) |
C20—C31 | 1.524 (4) | C70—C81 | 1.514 (4) |
C21—C22 | 1.359 (4) | C71—C72 | 1.363 (4) |
C21—C30 | 1.405 (4) | C71—C80 | 1.414 (4) |
C22—C23 | 1.400 (4) | C72—C73 | 1.413 (4) |
C22—H22 | 0.9300 | C72—H72 | 0.9300 |
C23—C24 | 1.359 (5) | C73—C74 | 1.352 (4) |
C23—H23 | 0.9300 | C73—H73 | 0.9300 |
C24—C25 | 1.408 (5) | C74—C75 | 1.410 (4) |
C24—H24 | 0.9300 | C74—H74 | 0.9300 |
C25—C30 | 1.407 (4) | C75—C80 | 1.398 (4) |
C25—C26 | 1.427 (5) | C75—C76 | 1.418 (5) |
C26—C27 | 1.359 (4) | C76—C77 | 1.354 (4) |
C26—H26 | 0.9300 | C76—H76 | 0.9300 |
C27—C28 | 1.401 (4) | C77—C78 | 1.405 (4) |
C27—H27 | 0.9300 | C77—H77 | 0.9300 |
C28—C29 | 1.376 (4) | C78—C79 | 1.376 (4) |
C28—H28 | 0.9300 | C78—H78 | 0.9300 |
C29—C30 | 1.400 (4) | C79—C80 | 1.404 (4) |
C29—C31 | 1.478 (4) | C79—C81 | 1.473 (4) |
C31—N2 | 1.269 (3) | C81—N4 | 1.267 (3) |
C32—C37 | 1.394 (4) | C82—C87 | 1.385 (4) |
C32—C33 | 1.399 (4) | C82—C83 | 1.395 (4) |
C32—N2 | 1.423 (3) | C82—N4 | 1.420 (3) |
C33—C34 | 1.390 (4) | C83—C84 | 1.388 (4) |
C33—C38 | 1.485 (4) | C83—C88 | 1.488 (4) |
C34—C35 | 1.370 (4) | C84—C85 | 1.387 (4) |
C34—H34 | 0.9300 | C84—H84 | 0.9300 |
C35—C36 | 1.394 (4) | C85—C86 | 1.386 (4) |
C35—C44 | 1.511 (4) | C85—C94 | 1.508 (4) |
C36—C37 | 1.388 (4) | C86—C87 | 1.387 (4) |
C36—H36 | 0.9300 | C86—H86 | 0.9300 |
C37—C50 | 1.503 (4) | C87—C100 | 1.515 (4) |
C38—C43 | 1.371 (4) | C88—C93 | 1.374 (4) |
C38—C39 | 1.391 (4) | C88—C89 | 1.383 (4) |
C39—C40 | 1.386 (4) | C89—C90 | 1.384 (4) |
C39—H39 | 0.9300 | C89—H89 | 0.9300 |
C40—C41 | 1.367 (4) | C90—C91 | 1.377 (5) |
C40—H40 | 0.9300 | C90—H90 | 0.9300 |
C41—C42 | 1.359 (4) | C91—C92 | 1.366 (5) |
C41—H41 | 0.9300 | C91—H91 | 0.9300 |
C42—C43 | 1.377 (4) | C92—C93 | 1.382 (4) |
C42—H42 | 0.9300 | C92—H92 | 0.9300 |
C43—H43 | 0.9300 | C93—H93 | 0.9300 |
C44—C49 | 1.341 (4) | C94—C95 | 1.344 (4) |
C44—C45 | 1.365 (5) | C94—C99 | 1.365 (4) |
C45—C46 | 1.397 (5) | C95—C96 | 1.387 (4) |
C45—H45 | 0.9300 | C95—H95 | 0.9300 |
C46—C47 | 1.371 (6) | C96—C97 | 1.370 (5) |
C46—H46 | 0.9300 | C96—H96 | 0.9300 |
C47—C48 | 1.372 (6) | C97—C98 | 1.359 (5) |
C47—H47 | 0.9300 | C97—H97 | 0.9300 |
C48—C49 | 1.420 (5) | C98—C99 | 1.381 (4) |
C48—H48 | 0.9300 | C98—H98 | 0.9300 |
C49—H49 | 0.9300 | C99—H99 | 0.9300 |
C50—H50A | 0.9600 | C100—H10A | 0.9600 |
C50—H50B | 0.9600 | C100—H10B | 0.9600 |
C50—H50C | 0.9600 | C100—H10C | 0.9600 |
C8—C7—C12 | 120.0 | C56—C51—N3 | 120.7 (3) |
C8—C7—C4 | 119.9 (2) | C53—C52—C51 | 119.1 (3) |
C12—C7—C4 | 120.1 (2) | C53—C52—C69 | 120.2 (3) |
C9—C8—C7 | 120.0 | C51—C52—C69 | 120.7 (3) |
C9—C8—H8 | 120.0 | C52—C53—C54 | 121.9 (3) |
C7—C8—H8 | 120.0 | C52—C53—H53 | 119.0 |
C8—C9—C10 | 120.0 | C54—C53—H53 | 119.0 |
C8—C9—H9 | 120.0 | C55—C54—C53 | 117.4 (3) |
C10—C9—H9 | 120.0 | C55—C54—C57 | 121.9 (3) |
C9—C10—C11 | 120.0 | C53—C54—C57 | 120.6 (3) |
C9—C10—H10 | 120.0 | C56—C55—C54 | 122.4 (3) |
C11—C10—H10 | 120.0 | C56—C55—H55 | 118.8 |
C12—C11—C10 | 120.0 | C54—C55—H55 | 118.8 |
C12—C11—H11 | 120.0 | C55—C56—C51 | 118.2 (3) |
C10—C11—H11 | 120.0 | C55—C56—C63 | 118.5 (3) |
C11—C12—C7 | 120.0 | C51—C56—C63 | 123.3 (3) |
C11—C12—H12 | 120.0 | C58—C57—C62 | 118.9 (3) |
C7—C12—H12 | 120.0 | C58—C57—C54 | 121.8 (3) |
C2—C1—C6 | 120.2 (3) | C62—C57—C54 | 119.3 (3) |
C2—C1—N1 | 117.7 (3) | C57—C58—C59 | 121.9 (4) |
C6—C1—N1 | 122.0 (3) | C57—C58—H58 | 119.0 |
C1—C2—C3 | 119.4 (3) | C59—C58—H58 | 119.0 |
C1—C2—C19 | 120.7 (3) | C60—C59—C58 | 119.3 (4) |
C3—C2—C19 | 119.9 (3) | C60—C59—H59 | 120.3 |
C4—C3—C2 | 121.9 (3) | C58—C59—H59 | 120.3 |
C4—C3—H3 | 119.0 | C59—C60—C61 | 119.5 (4) |
C2—C3—H3 | 119.0 | C59—C60—H60 | 120.2 |
C5—C4—C3 | 116.5 (3) | C61—C60—H60 | 120.2 |
C5—C4—C7 | 122.9 (3) | C62—C61—C60 | 120.0 (4) |
C3—C4—C7 | 120.6 (3) | C62—C61—H61 | 120.0 |
C4—C5—C6 | 123.4 (3) | C60—C61—H61 | 120.0 |
C4—C5—H5 | 118.3 | C61—C62—C57 | 120.4 (3) |
C6—C5—H5 | 118.3 | C61—C62—H62 | 119.8 |
C1—C6—C5 | 118.4 (3) | C57—C62—H62 | 119.8 |
C1—C6—C13 | 122.4 (3) | C64—C63—C68 | 117.9 (3) |
C5—C6—C13 | 119.2 (3) | C64—C63—C56 | 120.3 (3) |
C14—C13—C18 | 116.8 (3) | C68—C63—C56 | 121.6 (3) |
C14—C13—C6 | 121.0 (3) | C65—C64—C63 | 121.9 (4) |
C18—C13—C6 | 122.2 (3) | C65—C64—H64 | 119.1 |
C13—C14—C15 | 121.0 (4) | C63—C64—H64 | 119.1 |
C13—C14—H14 | 119.5 | C66—C65—C64 | 120.3 (4) |
C15—C14—H14 | 119.5 | C66—C65—H65 | 119.8 |
C16—C15—C14 | 119.4 (4) | C64—C65—H65 | 119.8 |
C16—C15—H15 | 120.3 | C65—C66—C67 | 119.4 (5) |
C14—C15—H15 | 120.3 | C65—C66—H66 | 120.3 |
C17—C16—C15 | 120.6 (4) | C67—C66—H66 | 120.3 |
C17—C16—H16 | 119.7 | C66—C67—C68 | 120.7 (5) |
C15—C16—H16 | 119.7 | C66—C67—H67 | 119.7 |
C16—C17—C18 | 119.8 (4) | C68—C67—H67 | 119.7 |
C16—C17—H17 | 120.1 | C63—C68—C67 | 119.8 (4) |
C18—C17—H17 | 120.1 | C63—C68—H68 | 120.1 |
C17—C18—C13 | 122.4 (4) | C67—C68—H68 | 120.1 |
C17—C18—H18 | 118.8 | C52—C69—H69A | 109.5 |
C13—C18—H18 | 118.8 | C52—C69—H69B | 109.5 |
C2—C19—H19A | 109.5 | H69A—C69—H69B | 109.5 |
C2—C19—H19B | 109.5 | C52—C69—H69C | 109.5 |
H19A—C19—H19B | 109.5 | H69A—C69—H69C | 109.5 |
C2—C19—H19C | 109.5 | H69B—C69—H69C | 109.5 |
H19A—C19—H19C | 109.5 | N3—C70—C71 | 133.4 (3) |
H19B—C19—H19C | 109.5 | N3—C70—C81 | 119.4 (3) |
N1—C20—C21 | 133.3 (3) | C71—C70—C81 | 107.0 (3) |
N1—C20—C31 | 120.0 (3) | C72—C71—C80 | 118.4 (3) |
C21—C20—C31 | 106.7 (3) | C72—C71—C70 | 135.3 (3) |
C22—C21—C30 | 119.2 (3) | C80—C71—C70 | 106.3 (3) |
C22—C21—C20 | 134.4 (3) | C71—C72—C73 | 119.0 (3) |
C30—C21—C20 | 106.3 (3) | C71—C72—H72 | 120.5 |
C21—C22—C23 | 118.9 (3) | C73—C72—H72 | 120.5 |
C21—C22—H22 | 120.5 | C74—C73—C72 | 122.3 (3) |
C23—C22—H22 | 120.5 | C74—C73—H73 | 118.8 |
C24—C23—C22 | 122.7 (4) | C72—C73—H73 | 118.8 |
C24—C23—H23 | 118.6 | C73—C74—C75 | 120.8 (4) |
C22—C23—H23 | 118.6 | C73—C74—H74 | 119.6 |
C23—C24—C25 | 120.1 (4) | C75—C74—H74 | 119.6 |
C23—C24—H24 | 120.0 | C80—C75—C74 | 116.2 (3) |
C25—C24—H24 | 120.0 | C80—C75—C76 | 116.0 (3) |
C24—C25—C30 | 116.6 (3) | C74—C75—C76 | 127.8 (4) |
C24—C25—C26 | 127.7 (4) | C77—C76—C75 | 121.0 (4) |
C30—C25—C26 | 115.7 (4) | C77—C76—H76 | 119.5 |
C27—C26—C25 | 120.3 (4) | C75—C76—H76 | 119.5 |
C27—C26—H26 | 119.8 | C76—C77—C78 | 122.3 (4) |
C25—C26—H26 | 119.8 | C76—C77—H77 | 118.8 |
C26—C27—C28 | 123.1 (4) | C78—C77—H77 | 118.8 |
C26—C27—H27 | 118.4 | C79—C78—C77 | 118.5 (3) |
C28—C27—H27 | 118.4 | C79—C78—H78 | 120.7 |
C29—C28—C27 | 118.3 (3) | C77—C78—H78 | 120.7 |
C29—C28—H28 | 120.8 | C78—C79—C80 | 119.1 (3) |
C27—C28—H28 | 120.8 | C78—C79—C81 | 134.4 (3) |
C28—C29—C30 | 119.2 (3) | C80—C79—C81 | 106.5 (3) |
C28—C29—C31 | 134.2 (3) | C75—C80—C79 | 123.0 (3) |
C30—C29—C31 | 106.6 (3) | C75—C80—C71 | 123.3 (3) |
C29—C30—C21 | 114.3 (3) | C79—C80—C71 | 113.7 (3) |
C29—C30—C25 | 123.3 (3) | N4—C81—C79 | 132.5 (3) |
C21—C30—C25 | 122.3 (3) | N4—C81—C70 | 121.1 (3) |
N2—C31—C29 | 133.1 (3) | C79—C81—C70 | 106.4 (3) |
N2—C31—C20 | 120.8 (3) | C87—C82—C83 | 121.0 (3) |
C29—C31—C20 | 106.1 (3) | C87—C82—N4 | 117.8 (3) |
C37—C32—C33 | 121.1 (3) | C83—C82—N4 | 121.2 (3) |
C37—C32—N2 | 118.2 (3) | C84—C83—C82 | 117.8 (3) |
C33—C32—N2 | 120.5 (3) | C84—C83—C88 | 120.0 (3) |
C34—C33—C32 | 117.5 (3) | C82—C83—C88 | 122.1 (3) |
C34—C33—C38 | 120.1 (3) | C85—C84—C83 | 122.9 (3) |
C32—C33—C38 | 122.4 (3) | C85—C84—H84 | 118.5 |
C35—C34—C33 | 123.5 (3) | C83—C84—H84 | 118.5 |
C35—C34—H34 | 118.2 | C86—C85—C84 | 117.1 (3) |
C33—C34—H34 | 118.2 | C86—C85—C94 | 121.4 (3) |
C34—C35—C36 | 117.0 (3) | C84—C85—C94 | 121.5 (3) |
C34—C35—C44 | 121.6 (3) | C85—C86—C87 | 122.1 (3) |
C36—C35—C44 | 121.4 (3) | C85—C86—H86 | 118.9 |
C37—C36—C35 | 122.5 (3) | C87—C86—H86 | 118.9 |
C37—C36—H36 | 118.8 | C82—C87—C86 | 118.9 (3) |
C35—C36—H36 | 118.8 | C82—C87—C100 | 121.3 (3) |
C36—C37—C32 | 118.1 (3) | C86—C87—C100 | 119.8 (3) |
C36—C37—C50 | 121.0 (3) | C93—C88—C89 | 117.3 (3) |
C32—C37—C50 | 120.9 (3) | C93—C88—C83 | 120.7 (3) |
C43—C38—C39 | 117.3 (3) | C89—C88—C83 | 122.0 (3) |
C43—C38—C33 | 121.3 (3) | C90—C89—C88 | 121.5 (3) |
C39—C38—C33 | 121.3 (3) | C90—C89—H89 | 119.2 |
C40—C39—C38 | 120.2 (3) | C88—C89—H89 | 119.2 |
C40—C39—H39 | 119.9 | C91—C90—C89 | 119.4 (4) |
C38—C39—H39 | 119.9 | C91—C90—H90 | 120.3 |
C41—C40—C39 | 121.1 (3) | C89—C90—H90 | 120.3 |
C41—C40—H40 | 119.4 | C92—C91—C90 | 120.2 (4) |
C39—C40—H40 | 119.4 | C92—C91—H91 | 119.9 |
C42—C41—C40 | 118.9 (4) | C90—C91—H91 | 119.9 |
C42—C41—H41 | 120.6 | C91—C92—C93 | 119.4 (4) |
C40—C41—H41 | 120.6 | C91—C92—H92 | 120.3 |
C41—C42—C43 | 120.5 (4) | C93—C92—H92 | 120.3 |
C41—C42—H42 | 119.8 | C88—C93—C92 | 122.2 (3) |
C43—C42—H42 | 119.8 | C88—C93—H93 | 118.9 |
C38—C43—C42 | 122.0 (3) | C92—C93—H93 | 118.9 |
C38—C43—H43 | 119.0 | C95—C94—C99 | 119.0 (3) |
C42—C43—H43 | 119.0 | C95—C94—C85 | 120.8 (3) |
C49—C44—C45 | 119.5 (3) | C99—C94—C85 | 120.1 (3) |
C49—C44—C35 | 121.1 (4) | C94—C95—C96 | 121.5 (3) |
C45—C44—C35 | 119.4 (4) | C94—C95—H95 | 119.3 |
C44—C45—C46 | 120.9 (4) | C96—C95—H95 | 119.3 |
C44—C45—H45 | 119.5 | C97—C96—C95 | 119.3 (4) |
C46—C45—H45 | 119.5 | C97—C96—H96 | 120.3 |
C47—C46—C45 | 119.3 (5) | C95—C96—H96 | 120.3 |
C47—C46—H46 | 120.3 | C98—C97—C96 | 119.4 (4) |
C45—C46—H46 | 120.3 | C98—C97—H97 | 120.3 |
C46—C47—C48 | 120.6 (5) | C96—C97—H97 | 120.3 |
C46—C47—H47 | 119.7 | C97—C98—C99 | 120.4 (4) |
C48—C47—H47 | 119.7 | C97—C98—H98 | 119.8 |
C47—C48—C49 | 118.2 (5) | C99—C98—H98 | 119.8 |
C47—C48—H48 | 120.9 | C94—C99—C98 | 120.4 (4) |
C49—C48—H48 | 120.9 | C94—C99—H99 | 119.8 |
C44—C49—C48 | 121.5 (4) | C98—C99—H99 | 119.8 |
C44—C49—H49 | 119.3 | C87—C100—H10A | 109.5 |
C48—C49—H49 | 119.3 | C87—C100—H10B | 109.5 |
C37—C50—H50A | 109.5 | H10A—C100—H10B | 109.5 |
C37—C50—H50B | 109.5 | C87—C100—H10C | 109.5 |
H50A—C50—H50B | 109.5 | H10A—C100—H10C | 109.5 |
C37—C50—H50C | 109.5 | H10B—C100—H10C | 109.5 |
H50A—C50—H50C | 109.5 | C20—N1—C1 | 120.5 (3) |
H50B—C50—H50C | 109.5 | C31—N2—C32 | 119.7 (3) |
C52—C51—C56 | 120.9 (3) | C70—N3—C51 | 121.9 (3) |
C52—C51—N3 | 118.2 (3) | C81—N4—C82 | 118.8 (3) |
C12—C7—C8—C9 | 0.0 | C53—C54—C55—C56 | −0.5 (4) |
C4—C7—C8—C9 | −177.5 (2) | C57—C54—C55—C56 | 179.8 (3) |
C7—C8—C9—C10 | 0.0 | C54—C55—C56—C51 | 0.2 (4) |
C8—C9—C10—C11 | 0.0 | C54—C55—C56—C63 | 179.9 (3) |
C9—C10—C11—C12 | 0.0 | C52—C51—C56—C55 | 0.4 (4) |
C10—C11—C12—C7 | 0.0 | N3—C51—C56—C55 | 176.2 (3) |
C8—C7—C12—C11 | 0.0 | C52—C51—C56—C63 | −179.4 (3) |
C4—C7—C12—C11 | 177.5 (2) | N3—C51—C56—C63 | −3.6 (4) |
C6—C1—C2—C3 | 1.4 (5) | C55—C54—C57—C58 | −147.3 (3) |
N1—C1—C2—C3 | 177.3 (3) | C53—C54—C57—C58 | 33.1 (5) |
C6—C1—C2—C19 | 179.7 (3) | C55—C54—C57—C62 | 30.7 (4) |
N1—C1—C2—C19 | −4.4 (5) | C53—C54—C57—C62 | −148.9 (3) |
C1—C2—C3—C4 | 2.2 (5) | C62—C57—C58—C59 | −1.7 (5) |
C19—C2—C3—C4 | −176.1 (3) | C54—C57—C58—C59 | 176.3 (3) |
C2—C3—C4—C5 | −3.0 (5) | C57—C58—C59—C60 | 0.8 (6) |
C2—C3—C4—C7 | 176.1 (3) | C58—C59—C60—C61 | 0.8 (6) |
C8—C7—C4—C5 | 161.4 (2) | C59—C60—C61—C62 | −1.4 (5) |
C12—C7—C4—C5 | −16.1 (4) | C60—C61—C62—C57 | 0.6 (5) |
C8—C7—C4—C3 | −17.6 (3) | C58—C57—C62—C61 | 1.0 (5) |
C12—C7—C4—C3 | 164.9 (2) | C54—C57—C62—C61 | −177.1 (3) |
C3—C4—C5—C6 | 0.2 (4) | C55—C56—C63—C64 | 41.2 (4) |
C7—C4—C5—C6 | −178.8 (3) | C51—C56—C63—C64 | −139.1 (3) |
C2—C1—C6—C5 | −4.0 (4) | C55—C56—C63—C68 | −133.8 (3) |
N1—C1—C6—C5 | −179.7 (3) | C51—C56—C63—C68 | 46.0 (4) |
C2—C1—C6—C13 | 176.1 (3) | C68—C63—C64—C65 | 0.1 (5) |
N1—C1—C6—C13 | 0.4 (4) | C56—C63—C64—C65 | −175.1 (3) |
C4—C5—C6—C1 | 3.2 (4) | C63—C64—C65—C66 | 0.5 (6) |
C4—C5—C6—C13 | −176.9 (3) | C64—C65—C66—C67 | −1.3 (7) |
C1—C6—C13—C14 | 139.5 (3) | C65—C66—C67—C68 | 1.5 (7) |
C5—C6—C13—C14 | −40.3 (4) | C64—C63—C68—C67 | 0.2 (5) |
C1—C6—C13—C18 | −42.4 (4) | C56—C63—C68—C67 | 175.3 (3) |
C5—C6—C13—C18 | 137.7 (3) | C66—C67—C68—C63 | −1.0 (6) |
C18—C13—C14—C15 | −0.5 (5) | N3—C70—C71—C72 | −6.8 (6) |
C6—C13—C14—C15 | 177.6 (3) | C81—C70—C71—C72 | 177.2 (3) |
C13—C14—C15—C16 | 1.6 (5) | N3—C70—C71—C80 | 173.5 (3) |
C14—C15—C16—C17 | −2.1 (6) | C81—C70—C71—C80 | −2.4 (3) |
C15—C16—C17—C18 | 1.5 (6) | C80—C71—C72—C73 | −0.1 (5) |
C16—C17—C18—C13 | −0.5 (6) | C70—C71—C72—C73 | −179.7 (3) |
C14—C13—C18—C17 | 0.0 (5) | C71—C72—C73—C74 | −0.6 (5) |
C6—C13—C18—C17 | −178.1 (3) | C72—C73—C74—C75 | 0.3 (6) |
N1—C20—C21—C22 | −4.0 (6) | C73—C74—C75—C80 | 0.5 (5) |
C31—C20—C21—C22 | 175.6 (3) | C73—C74—C75—C76 | 179.1 (4) |
N1—C20—C21—C30 | 179.6 (3) | C80—C75—C76—C77 | −0.1 (5) |
C31—C20—C21—C30 | −0.9 (3) | C74—C75—C76—C77 | −178.6 (4) |
C30—C21—C22—C23 | −1.1 (5) | C75—C76—C77—C78 | 0.0 (6) |
C20—C21—C22—C23 | −177.2 (3) | C76—C77—C78—C79 | 0.3 (5) |
C21—C22—C23—C24 | −0.6 (6) | C77—C78—C79—C80 | −0.6 (5) |
C22—C23—C24—C25 | 0.8 (6) | C77—C78—C79—C81 | 178.6 (3) |
C23—C24—C25—C30 | 0.7 (5) | C74—C75—C80—C79 | 178.5 (3) |
C23—C24—C25—C26 | 179.1 (4) | C76—C75—C80—C79 | −0.3 (5) |
C24—C25—C26—C27 | −177.8 (4) | C74—C75—C80—C71 | −1.2 (5) |
C30—C25—C26—C27 | 0.6 (5) | C76—C75—C80—C71 | −179.9 (3) |
C25—C26—C27—C28 | 0.7 (6) | C78—C79—C80—C75 | 0.6 (5) |
C26—C27—C28—C29 | −1.3 (6) | C81—C79—C80—C75 | −178.8 (3) |
C27—C28—C29—C30 | 0.5 (5) | C78—C79—C80—C71 | −179.7 (3) |
C27—C28—C29—C31 | −179.7 (3) | C81—C79—C80—C71 | 0.9 (3) |
C28—C29—C30—C21 | −179.4 (3) | C72—C71—C80—C75 | 1.0 (5) |
C31—C29—C30—C21 | 0.8 (4) | C70—C71—C80—C75 | −179.3 (3) |
C28—C29—C30—C25 | 0.9 (5) | C72—C71—C80—C79 | −178.7 (3) |
C31—C29—C30—C25 | −179.0 (3) | C70—C71—C80—C79 | 1.0 (3) |
C22—C21—C30—C29 | −177.0 (3) | C78—C79—C81—N4 | −3.9 (6) |
C20—C21—C30—C29 | 0.1 (4) | C80—C79—C81—N4 | 175.4 (3) |
C22—C21—C30—C25 | 2.7 (5) | C78—C79—C81—C70 | 178.4 (3) |
C20—C21—C30—C25 | 179.9 (3) | C80—C79—C81—C70 | −2.3 (3) |
C24—C25—C30—C29 | 177.2 (3) | N3—C70—C81—N4 | 8.3 (4) |
C26—C25—C30—C29 | −1.4 (5) | C71—C70—C81—N4 | −175.1 (3) |
C24—C25—C30—C21 | −2.5 (5) | N3—C70—C81—C79 | −173.6 (3) |
C26—C25—C30—C21 | 178.9 (3) | C71—C70—C81—C79 | 3.0 (3) |
C28—C29—C31—N2 | −0.5 (6) | C87—C82—C83—C84 | 3.2 (4) |
C30—C29—C31—N2 | 179.3 (3) | N4—C82—C83—C84 | −178.7 (3) |
C28—C29—C31—C20 | 178.9 (3) | C87—C82—C83—C88 | −179.3 (3) |
C30—C29—C31—C20 | −1.3 (3) | N4—C82—C83—C88 | −1.2 (4) |
N1—C20—C31—N2 | 0.4 (4) | C82—C83—C84—C85 | −1.1 (4) |
C21—C20—C31—N2 | −179.1 (3) | C88—C83—C84—C85 | −178.6 (3) |
N1—C20—C31—C29 | −179.0 (3) | C83—C84—C85—C86 | −1.5 (4) |
C21—C20—C31—C29 | 1.4 (3) | C83—C84—C85—C94 | 178.3 (3) |
C37—C32—C33—C34 | −4.4 (5) | C84—C85—C86—C87 | 2.1 (5) |
N2—C32—C33—C34 | −179.9 (3) | C94—C85—C86—C87 | −177.6 (3) |
C37—C32—C33—C38 | 175.4 (3) | C83—C82—C87—C86 | −2.7 (5) |
N2—C32—C33—C38 | −0.1 (5) | N4—C82—C87—C86 | 179.2 (3) |
C32—C33—C34—C35 | 0.2 (5) | C83—C82—C87—C100 | 179.9 (3) |
C38—C33—C34—C35 | −179.6 (3) | N4—C82—C87—C100 | 1.7 (5) |
C33—C34—C35—C36 | 3.7 (5) | C85—C86—C87—C82 | −0.1 (5) |
C33—C34—C35—C44 | −176.5 (3) | C85—C86—C87—C100 | 177.4 (3) |
C34—C35—C36—C37 | −3.8 (5) | C84—C83—C88—C93 | 40.2 (4) |
C44—C35—C36—C37 | 176.4 (3) | C82—C83—C88—C93 | −137.1 (3) |
C35—C36—C37—C32 | −0.1 (5) | C84—C83—C88—C89 | −137.4 (3) |
C35—C36—C37—C50 | −178.7 (3) | C82—C83—C88—C89 | 45.2 (4) |
C33—C32—C37—C36 | 4.3 (5) | C93—C88—C89—C90 | −0.2 (5) |
N2—C32—C37—C36 | 179.9 (3) | C83—C88—C89—C90 | 177.6 (3) |
C33—C32—C37—C50 | −177.1 (3) | C88—C89—C90—C91 | 0.1 (5) |
N2—C32—C37—C50 | −1.5 (5) | C89—C90—C91—C92 | −0.4 (6) |
C34—C33—C38—C43 | −42.3 (4) | C90—C91—C92—C93 | 0.8 (6) |
C32—C33—C38—C43 | 137.9 (3) | C89—C88—C93—C92 | 0.5 (5) |
C34—C33—C38—C39 | 134.9 (3) | C83—C88—C93—C92 | −177.2 (3) |
C32—C33—C38—C39 | −44.9 (4) | C91—C92—C93—C88 | −0.9 (5) |
C43—C38—C39—C40 | 0.7 (5) | C86—C85—C94—C95 | 145.4 (3) |
C33—C38—C39—C40 | −176.6 (3) | C84—C85—C94—C95 | −34.4 (4) |
C38—C39—C40—C41 | 0.3 (5) | C86—C85—C94—C99 | −31.5 (4) |
C39—C40—C41—C42 | −0.6 (5) | C84—C85—C94—C99 | 148.8 (3) |
C40—C41—C42—C43 | −0.2 (5) | C99—C94—C95—C96 | −1.9 (5) |
C39—C38—C43—C42 | −1.4 (5) | C85—C94—C95—C96 | −178.8 (3) |
C33—C38—C43—C42 | 175.9 (3) | C94—C95—C96—C97 | 1.2 (5) |
C41—C42—C43—C38 | 1.2 (5) | C95—C96—C97—C98 | 0.1 (6) |
C34—C35—C44—C49 | −147.9 (3) | C96—C97—C98—C99 | −0.8 (6) |
C36—C35—C44—C49 | 32.0 (5) | C95—C94—C99—C98 | 1.2 (5) |
C34—C35—C44—C45 | 32.9 (5) | C85—C94—C99—C98 | 178.1 (3) |
C36—C35—C44—C45 | −147.3 (4) | C97—C98—C99—C94 | 0.2 (5) |
C49—C44—C45—C46 | −1.2 (6) | C21—C20—N1—C1 | −2.1 (5) |
C35—C44—C45—C46 | 178.1 (3) | C31—C20—N1—C1 | 178.5 (3) |
C44—C45—C46—C47 | 1.1 (6) | C2—C1—N1—C20 | 103.1 (3) |
C45—C46—C47—C48 | −1.2 (7) | C6—C1—N1—C20 | −81.1 (4) |
C46—C47—C48—C49 | 1.3 (7) | C29—C31—N2—C32 | −4.2 (5) |
C45—C44—C49—C48 | 1.3 (6) | C20—C31—N2—C32 | 176.4 (3) |
C35—C44—C49—C48 | −178.0 (3) | C37—C32—N2—C31 | 100.5 (4) |
C47—C48—C49—C44 | −1.4 (6) | C33—C32—N2—C31 | −83.9 (4) |
C56—C51—C52—C53 | −0.5 (4) | C71—C70—N3—C51 | 2.7 (5) |
N3—C51—C52—C53 | −176.4 (3) | C81—C70—N3—C51 | 178.3 (3) |
C56—C51—C52—C69 | 178.2 (3) | C52—C51—N3—C70 | −97.4 (3) |
N3—C51—C52—C69 | 2.3 (4) | C56—C51—N3—C70 | 86.7 (4) |
C51—C52—C53—C54 | 0.1 (5) | C79—C81—N4—C82 | 2.4 (5) |
C69—C52—C53—C54 | −178.6 (3) | C70—C81—N4—C82 | 179.9 (3) |
C52—C53—C54—C55 | 0.4 (5) | C87—C82—N4—C81 | −95.6 (3) |
C52—C53—C54—C57 | −180.0 (3) | C83—C82—N4—C81 | 86.3 (4) |
Cg2 is the centroid of ring C1–C6 in molecule A. |
D—H···A | D—H | H···A | D···A | D—H···A |
C16—H16···N3i | 0.93 | 2.60 | 3.517 (6) | 168 |
C92—H92···Cg2ii | 0.93 | 2.95 | 3.789 (5) | 151 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x+1, y, z−1. |
Cg2 is the centroid of ring C1–C6 in molecule A. |
D—H···A | D—H | H···A | D···A | D—H···A |
C16—H16···N3i | 0.93 | 2.60 | 3.517 (6) | 168 |
C92—H92···Cg2ii | 0.93 | 2.95 | 3.789 (5) | 151 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x+1, y, z−1. |
Experimental details
Crystal data | |
Chemical formula | C50H36N2 |
Mr | 664.81 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 296 |
a, b, c (Å) | 15.579 (3), 16.799 (4), 17.332 (4) |
α, β, γ (°) | 72.622 (2), 73.116 (2), 84.324 (2) |
V (Å3) | 4142.0 (15) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.06 |
Crystal size (mm) | 0.23 × 0.21 × 0.16 |
Data collection | |
Diffractometer | Bruker APEXII CCD |
Absorption correction | Multi-scan (SADABS; Bruker, 2008) |
Tmin, Tmax | 0.986, 0.990 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 29357, 14707, 5868 |
Rint | 0.041 |
(sin θ/λ)max (Å−1) | 0.599 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.065, 0.144, 1.04 |
No. of reflections | 14707 |
No. of parameters | 930 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.24, −0.29 |
Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), PLATON (Spek, 2009) and Mercury (Macrae et al., 2008), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).
Acknowledgements
We thank the Key Laboratory of Bioelectrochemical and Environmental Analysis of Gansu Province, College of Chemistry and Chemical Engineering, (Northwest Normal University), for financial support.
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