organic compounds
1-(3′,6′-Dihydroxy-3-oxo-3H-spiro[isobenzofuran-1,9′-xanthen]-5-yl)-3-[4-({4-[1-(4-fluorophenyl)-1H-imidazol-5-yl]pyridin-2-yl}amino)phenyl]thiourea methanol monosolvate
aInstitute of Pharmaceutical Sciences, Department of Pharmaceutical and Medicinal Chemistry, Eberhard Karls Universität Tübingen, Auf der Morgenstelle 8, 72076 Tübingen, Germany, and bDepartment of Organic Chemistry, Johannes Gutenberg-University Mainz, Duesbergweg 10-14, 55099 Mainz, Germany
*Correspondence e-mail: pierre.koch@uni-tuebingen.de
The title compound, which crystallized as a methanol monosolvate, C41H27FN6O5S·CH3OH, was synthesized as a probe for a fluorescence polarization-based competition binding assay. The isobenzofuran fused-ring system is close to planar and orientated almost perpendicular to the central ring of the xanthene system. The dihedral angle between the benzene rings of the xanthene system is 10.0 (2)°, indicating a butterfly-like orientation. A short intramolecular C—F⋯π contact [F⋯π = 3.100 (4) Å and C—F⋯π = 139.9 (3)°] to the six-membered ring of the isobenzofuran system may influence the molecular conformation. The methanol solvent molecule is disordered over two orientations in a 0.6:0.4 ratio. In the crystal, the components are linked by numerous hydrogen bonds, generating a three-dimensional network.
Keywords: crystal structure; fluorescein; thiourea; pyridinylimidazole.
CCDC reference: 1481316
Structure description
The title compound was synthesized by reaction of N1-{4-[1-(4-fluorophenyl)-1H-imidazol-5-yl]pyridin-2-yl}benzene-1,4-diamine and 5(6)-fluorescein-isothiocyanate as a probe for a fluorescence polarization-based competition binding assay. The design and application of similar probes was recently published by our group (Ansideri et al., 2016). As a commercially available isomeric mixture of the 5′- and 6′-isomers of fluorescein-isothiocyanate had been used as a staring material, single-crystal analysis was performed to confirm the isolated isomer. X-ray data confirmed that solely the 5′-isomer was isolated. The title molecule is shown in Fig. 1.
The isobenzofuran fused-ring system is almost planar (r.m.s. deviation = 0.038 Å) and almost perpendicular to the central ring of the xanthene system [dihedral angle = 86.44 (17)°]. The dihedral angle between the benzene rings of the xanthene system is 10.0 (2)°. The thiourea unit of the molecule makes dihedral angles of 53.64 (17)° and 56.3 (2)° with the isobenzofuran ring system and the phenyl ring at the pyridine-C2 position, respectively. The imidazole ring makes a dihedral angle of 14.8 (3)° with the 4-fluorophenyl ring. The pyridine ring is almost perpendicular to the imidazole core, subtending a dihedral angle of 84.9 (3)°. A short intramolecular C—F⋯π contact [F⋯π = 3.100 (4) Å and C—F⋯π = 139.9 (3)°] to the six-membered ring of the isobenzofuran system may influence the molecular conformation.
The crystal packing features numerous hydrogen bonds (Table 1), generating a three-dimensional network, and incorporates one disordered molecule of methanol.
Synthesis and crystallization
A solution of N1-{4-[1-(4-fluorophenyl)-1H-imidazol-5-yl]pyridin-2-yl}benzene-1,4-diamine (200 mg, 0.58 mmol) and 5(6)-fluorescein-isothiocyanate (248 mg, 0.77 mmol) in acetone (30 ml) was stirred at 298 K for 48 h with light excluded. The mixture was evaporated to dryness and the residue was purified by flash (dichloromethane–ethanol 95:05–90:10) obtaining 160 mg of the desired product (yield 37%). Crystals of the title compound suitable for X-ray diffraction were obtained by slow evaporation of a solution of the solid in methanol at 298 K.
1H NMR (250 MHz, DMSO-d6): δ 6.45 (dd, J1 = 5.3 Hz, J2 = 1.4 Hz, 1H), 6.53–6.63 (m, 5H), 6.67 (d, J = 2.0 Hz, 2H), 7.18 (d, J = 8.4 Hz, 1H), 7.27 (d, J = 8.9 Hz, 2H), 7.35–7.45 (m, 5H), 7.47 (d, J = 9.0 Hz, 2H), 7.82 (dd, J1 = 8.4 Hz, J2 = 2.0 Hz), 8.00 (d, J = 1.0 Hz, 1H), 8.05 (d, J = 5.4 Hz, 1H), 8.17 (d, J = 1.9 Hz, 1H), 9.06 (br s, 1H), 9.94 (br s, 1H), 10.00 (s, 1H), 10.17 (s, 2H); 13C NMR (100 MHz, DMSO-d6) δ 83.6, 102.9, 108.3, 111.4, 113.3, 113.4, 117.3 (d, J = 22.9 Hz), 118.4, 119.1, 124.6, 125.7, 127.2, 128.7 (d, J = 8.8 Hz), 129.8, 130.8, 131.3, 132.7, 133.3 (d, J = 2.4 Hz), 138.4, 139.6, 141.8, 142.3, 148.5, 148.7, 152.8, 156.9, 160.5, 162.6 (d, J = 245.6 Hz), 169.6, 180.8. HPLC: t = 11.54 min, purity: 98% (λ = 254 nm).
Refinement
Crystal data, data collection and structure . The methanol solvent molecule is disordered over two orientations in a 0.6:0.4 ratio.
details are summarized in Table 2
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Structural data
CCDC reference: 1481316
10.1107/S2414314616008403/hb4047sup1.cif
contains datablocks I, New_Global_Publ_Block. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2414314616008403/hb4047Isup2.hkl
Supporting information file. DOI: 10.1107/S2414314616008403/hb4047Isup3.cml
A solution of N1-{4-[1-(4-fluorophenyl)-1H-imidazol-5-yl]pyridin-2-yl}benzene-1,4-diamine (200 mg, 0.58 mmol) and 5(6)-fluorescein-isothiocyanate (248 mg, 0.77 mmol) in acetone (30 ml) was stirred at 298 K for 48 h covered from light. The mixture was concentrated to dryness and the residue was purified by flash
(dichloromethane–ethanol 95:05–90:10) obtaining 160 mg of the desired product (yield 37%). Crystals of the title compound suitable for X-ray diffraction were obtained by slow evaporation of a solution of the solid in methanol at 298 K.1H NMR (250 MHz, DMSO-d6): δ 6.45 (dd, J1 = 5.3 Hz, J2 = 1.4 Hz, 1H), 6.53–6.63 (m, 5H), 6.67 (d, J = 2.0 Hz, 2H), 7.18 (d, J = 8.4 Hz, 1H), 7.27 (d, J = 8.9 Hz, 2H), 7.35–7.45 (m, 5H), 7.47 (d, J = 9.0 Hz, 2H), 7.82 (dd, J1 = 8.4 Hz, J2 = 2.0 Hz), 8.00 (d, J = 1.0 Hz, 1H), 8.05 (d, J = 5.4 Hz, 1H), 8.17 (d, J = 1.9 Hz, 1H), 9.06 (br s, 1H), 9.94 (br s, 1H), 10.00 (s, 1H), 10.17 (s, 2H); 13C NMR (100 MHz, DMSO-d6) δ 83.6, 102.9, 108.3, 111.4, 113.3, 113.4, 117.3 (d, J = 22.9 Hz), 118.4, 119.1, 124.6, 125.7, 127.2, 128.7 (d, J = 8.8 Hz), 129.8, 130.8, 131.3, 132.7, 133.3 (d, J = 2.4 Hz), 138.4, 139.6, 141.8, 142.3, 148.5, 148.7, 152.8, 156.9, 160.5, 162.6 (d, J = 245.6 Hz), 169.6, 180.8. HPLC: t = 11.54 min, purity: 98% (λ = 254 nm).
The title compound was synthesized by reaction of N1-{4-[1-(4-fluorophenyl)-1H-imidazol-5-yl]pyridin-2-yl}benzene-1,4-diamine and 5(6)-fluorescein-isothiocyanate as a probe for a fluorescence polarization-based competition binding assay. The design and application of similar probes was recently published by our group (Ansideri et al., 2016). As a commercially available isomeric mixture of the 5'- and 6'-isomers of fluorescein-isothiocyanate had been used as a staring material, single-crystal analysis was performed to confirm the isolated isomer. X-ray data confirmed that solely the 5'-isomer was isolated.
The isobenzofuran fused-ring system is almost planar (r.m.s. deviation = 0.038 Å) and almost perpendicular to the central ring of the xanthene system [dihedral angle = 86.44 (17)°]. The dihedral angle between the benzene rings of the xanthene system is 10.0 (2)°. The thiourea unit of the molecule makes dihedral angles of 53.64 (17)° and 56.3 (2)° with the isobenzofuran ring system and the phenyl ring at the pyridine-C2 position, respectively. The imidazole ring makes a dihedral angle of 14.8 (3)° with the 4-fluorophenyl ring. The pyridine ring is almost perpendicular to the imidazole core, subtending a dihedral angle of 84.9 (3)°. A short intramolecular C—F···π contact [F···π = 3.100 (4) Å and C—F···π = 139.9 (3)°] to the six-membered ring of the isobenzofuran system may influence the molecular conformation.
The crystal packing features numerous hydrogen bonds (Table 1), generating a three-dimensional network, and incorporates one disordered molecule of methanol.
Data collection: X-AREA (Stoe & Cie, 2011); cell
X-AREA (Stoe & Cie, 2011; data reduction: X-RED (Stoe & Cie, 2011; program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015).Fig. 1. The molecular structure of the title compound, with displacement ellipsoids drawn at the 50% probability level. |
C41H27FN6O5S·CH4O | F(000) = 3184 |
Mr = 766.79 | Dx = 1.442 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 15.1825 (8) Å | Cell parameters from 7245 reflections |
b = 17.7557 (7) Å | θ = 2.3–27.9° |
c = 26.2236 (13) Å | µ = 0.16 mm−1 |
β = 92.283 (4)° | T = 193 K |
V = 7063.6 (6) Å3 | Block, colourless |
Z = 8 | 0.09 × 0.08 × 0.07 mm |
Stoe IPDS 2T diffractometer | 3244 reflections with I > 2σ(I) |
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus | Rint = 0.085 |
Detector resolution: 6.67 pixels mm-1 | θmax = 28.6°, θmin = 2.3° |
rotation method scans | h = −20→20 |
23065 measured reflections | k = −21→23 |
8960 independent reflections | l = −35→35 |
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.070 | w = 1/[σ2(Fo2) + (0.110P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.240 | (Δ/σ)max < 0.001 |
S = 0.92 | Δρmax = 0.35 e Å−3 |
8960 reflections | Δρmin = −0.38 e Å−3 |
516 parameters | Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
2 restraints | Extinction coefficient: 0.00101 (19) |
C41H27FN6O5S·CH4O | V = 7063.6 (6) Å3 |
Mr = 766.79 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 15.1825 (8) Å | µ = 0.16 mm−1 |
b = 17.7557 (7) Å | T = 193 K |
c = 26.2236 (13) Å | 0.09 × 0.08 × 0.07 mm |
β = 92.283 (4)° |
Stoe IPDS 2T diffractometer | 3244 reflections with I > 2σ(I) |
23065 measured reflections | Rint = 0.085 |
8960 independent reflections |
R[F2 > 2σ(F2)] = 0.070 | 2 restraints |
wR(F2) = 0.240 | H-atom parameters constrained |
S = 0.92 | Δρmax = 0.35 e Å−3 |
8960 reflections | Δρmin = −0.38 e Å−3 |
516 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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
C1 | 0.7146 (3) | 0.0416 (2) | 0.45826 (18) | 0.0456 (10) | |
C2 | 0.7446 (3) | −0.0387 (2) | 0.45478 (17) | 0.0438 (9) | |
C3 | 0.6854 (3) | −0.0980 (2) | 0.45158 (19) | 0.0491 (11) | |
H3 | 0.6242 | −0.0874 | 0.4526 | 0.059* | |
C4 | 0.7120 (3) | −0.1717 (2) | 0.44691 (18) | 0.0485 (10) | |
H4 | 0.6698 | −0.2113 | 0.4457 | 0.058* | |
C5 | 0.8021 (3) | −0.1878 (2) | 0.44396 (18) | 0.0466 (10) | |
C6 | 0.8623 (3) | −0.1298 (2) | 0.44888 (19) | 0.0503 (11) | |
H6 | 0.9237 | −0.1402 | 0.4484 | 0.060* | |
C7 | 0.8333 (3) | −0.0563 (2) | 0.45448 (18) | 0.0469 (10) | |
O8 | 0.89947 (18) | −0.00298 (16) | 0.45973 (14) | 0.0535 (8) | |
C9 | 0.8766 (3) | 0.0723 (2) | 0.45771 (19) | 0.0467 (10) | |
C10 | 0.9461 (3) | 0.1221 (3) | 0.45871 (19) | 0.0519 (11) | |
H10 | 1.0050 | 0.1041 | 0.4617 | 0.062* | |
C11 | 0.9296 (3) | 0.1988 (3) | 0.4553 (2) | 0.0525 (11) | |
C12 | 0.8432 (3) | 0.2243 (3) | 0.4504 (2) | 0.0578 (12) | |
H12 | 0.8314 | 0.2767 | 0.4469 | 0.069* | |
C13 | 0.7748 (3) | 0.1734 (2) | 0.45061 (19) | 0.0523 (11) | |
H13 | 0.7158 | 0.1915 | 0.4481 | 0.063* | |
C14 | 0.7897 (3) | 0.0962 (2) | 0.45448 (18) | 0.0454 (10) | |
O15 | 0.83304 (19) | −0.25782 (16) | 0.43631 (13) | 0.0548 (8) | |
H15 | 0.7917 | −0.2856 | 0.4254 | 0.082* | |
O16 | 0.99968 (19) | 0.24600 (18) | 0.45616 (15) | 0.0636 (9) | |
H16 | 0.9845 | 0.2883 | 0.4672 | 0.095* | |
O17 | 0.67552 (18) | 0.05307 (17) | 0.51047 (12) | 0.0470 (7) | |
C18 | 0.5937 (3) | 0.0830 (2) | 0.50544 (18) | 0.0453 (10) | |
C19 | 0.5674 (3) | 0.0866 (2) | 0.45147 (18) | 0.0453 (10) | |
C20 | 0.6358 (3) | 0.0599 (2) | 0.42341 (18) | 0.0441 (10) | |
O21 | 0.5539 (2) | 0.10267 (18) | 0.54287 (13) | 0.0541 (8) | |
C22 | 0.4891 (3) | 0.1127 (2) | 0.42833 (18) | 0.0462 (10) | |
H22 | 0.4421 | 0.1305 | 0.4479 | 0.055* | |
C23 | 0.4827 (3) | 0.1116 (2) | 0.37583 (18) | 0.0470 (10) | |
C24 | 0.5513 (3) | 0.0831 (2) | 0.34715 (19) | 0.0488 (11) | |
H24 | 0.5447 | 0.0814 | 0.3110 | 0.059* | |
C25 | 0.6285 (3) | 0.0575 (3) | 0.37110 (19) | 0.0487 (11) | |
H25 | 0.6753 | 0.0387 | 0.3518 | 0.058* | |
N26 | 0.4075 (2) | 0.1462 (2) | 0.35115 (15) | 0.0497 (9) | |
H26 | 0.3989 | 0.2001 | 0.3703 | 0.060* | |
C27 | 0.3620 (3) | 0.1219 (3) | 0.30850 (18) | 0.0491 (11) | |
N28 | 0.3064 (2) | 0.1732 (2) | 0.28696 (16) | 0.0525 (9) | |
H28 | 0.2590 | 0.1411 | 0.2583 | 0.063* | |
S29 | 0.36943 (8) | 0.03475 (7) | 0.28470 (5) | 0.0582 (4) | |
C30 | 0.3108 (3) | 0.2532 (2) | 0.29427 (19) | 0.0511 (11) | |
C31 | 0.3902 (3) | 0.2919 (3) | 0.2939 (2) | 0.0591 (12) | |
H31 | 0.4438 | 0.2645 | 0.2924 | 0.071* | |
C32 | 0.3928 (3) | 0.3699 (3) | 0.2956 (2) | 0.0576 (12) | |
H32 | 0.4477 | 0.3955 | 0.2953 | 0.069* | |
C33 | 0.3145 (3) | 0.4108 (3) | 0.29767 (19) | 0.0513 (11) | |
C34 | 0.2351 (3) | 0.3715 (3) | 0.29846 (19) | 0.0527 (11) | |
H34 | 0.1812 | 0.3986 | 0.2995 | 0.063* | |
C35 | 0.2338 (3) | 0.2942 (3) | 0.29771 (19) | 0.0526 (11) | |
H35 | 0.1792 | 0.2684 | 0.2996 | 0.063* | |
N36 | 0.3091 (2) | 0.4896 (2) | 0.29414 (17) | 0.0570 (10) | |
H36 | 0.2562 | 0.5064 | 0.2850 | 0.068* | |
C37 | 0.3706 (3) | 0.5452 (3) | 0.30223 (19) | 0.0532 (11) | |
N38 | 0.3436 (3) | 0.6124 (3) | 0.2834 (2) | 0.0799 (15) | |
C39 | 0.3977 (5) | 0.6696 (4) | 0.2922 (4) | 0.126 (4) | |
H39 | 0.3783 | 0.7182 | 0.2815 | 0.151* | |
C40 | 0.4795 (5) | 0.6642 (4) | 0.3158 (3) | 0.115 (3) | |
H40 | 0.5173 | 0.7068 | 0.3177 | 0.138* | |
C41 | 0.5070 (3) | 0.5962 (3) | 0.3369 (2) | 0.0607 (13) | |
C42 | 0.4508 (3) | 0.5361 (3) | 0.32982 (19) | 0.0528 (11) | |
H42 | 0.4663 | 0.4882 | 0.3437 | 0.063* | |
C43 | 0.5906 (3) | 0.5970 (3) | 0.36659 (19) | 0.0534 (11) | |
N44 | 0.6417 (2) | 0.5368 (2) | 0.38405 (15) | 0.0509 (9) | |
C45 | 0.7124 (3) | 0.5661 (3) | 0.4102 (2) | 0.0561 (12) | |
H45 | 0.7584 | 0.5368 | 0.4257 | 0.067* | |
N46 | 0.7097 (2) | 0.6401 (2) | 0.41169 (16) | 0.0534 (9) | |
C47 | 0.6355 (3) | 0.6593 (3) | 0.38449 (19) | 0.0548 (11) | |
H47 | 0.6168 | 0.7097 | 0.3785 | 0.066* | |
C48 | 0.6348 (3) | 0.4580 (3) | 0.37468 (19) | 0.0523 (11) | |
C49 | 0.5898 (4) | 0.4127 (3) | 0.4064 (2) | 0.0721 (16) | |
H49 | 0.5584 | 0.4341 | 0.4335 | 0.087* | |
C50 | 0.5895 (4) | 0.3352 (3) | 0.3992 (3) | 0.0799 (18) | |
H50 | 0.5583 | 0.3030 | 0.4211 | 0.096* | |
C51 | 0.6341 (4) | 0.3071 (3) | 0.3607 (2) | 0.0675 (15) | |
C52 | 0.6814 (5) | 0.3505 (3) | 0.3291 (3) | 0.091 (2) | |
H52 | 0.7139 | 0.3286 | 0.3027 | 0.109* | |
C53 | 0.6807 (5) | 0.4272 (3) | 0.3365 (2) | 0.084 (2) | |
H53 | 0.7127 | 0.4590 | 0.3147 | 0.101* | |
F54 | 0.6336 (3) | 0.23112 (17) | 0.35271 (16) | 0.0939 (11) | |
C1L | 0.5122 (6) | 0.1316 (5) | 0.6625 (3) | 0.123 (3) | |
H1M | 0.4629 | 0.1554 | 0.6435 | 0.185* | 0.6 |
H2M | 0.5428 | 0.0971 | 0.6401 | 0.185* | 0.6 |
H3M | 0.5534 | 0.1705 | 0.6752 | 0.185* | 0.6 |
H4M | 0.5767 | 0.1337 | 0.6620 | 0.185* | 0.4 |
H5M | 0.4867 | 0.1573 | 0.6323 | 0.185* | 0.4 |
H6M | 0.4930 | 0.0789 | 0.6625 | 0.185* | 0.4 |
O1L | 0.4803 (5) | 0.0914 (5) | 0.7038 (3) | 0.111 (3) | 0.6 |
H1L | 0.5221 | 0.0681 | 0.7188 | 0.166* | 0.6 |
O2L | 0.4841 (7) | 0.1673 (5) | 0.7067 (3) | 0.081 (3) | 0.4 |
H2L | 0.4341 | 0.1864 | 0.7008 | 0.122* | 0.4 |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0352 (19) | 0.044 (2) | 0.057 (3) | 0.0036 (17) | −0.0048 (18) | −0.006 (2) |
C2 | 0.0364 (19) | 0.042 (2) | 0.052 (3) | 0.0047 (17) | −0.0059 (17) | −0.002 (2) |
C3 | 0.0342 (19) | 0.043 (2) | 0.070 (3) | 0.0017 (17) | 0.0030 (19) | −0.002 (2) |
C4 | 0.039 (2) | 0.038 (2) | 0.068 (3) | −0.0018 (17) | −0.0038 (19) | −0.003 (2) |
C5 | 0.044 (2) | 0.034 (2) | 0.061 (3) | 0.0040 (17) | −0.003 (2) | −0.0025 (19) |
C6 | 0.035 (2) | 0.043 (2) | 0.072 (3) | 0.0047 (17) | −0.003 (2) | −0.003 (2) |
C7 | 0.036 (2) | 0.045 (2) | 0.059 (3) | −0.0005 (17) | −0.0040 (19) | −0.006 (2) |
O8 | 0.0363 (14) | 0.0361 (15) | 0.087 (2) | 0.0002 (12) | −0.0070 (15) | −0.0041 (15) |
C9 | 0.043 (2) | 0.035 (2) | 0.062 (3) | −0.0002 (17) | −0.005 (2) | −0.005 (2) |
C10 | 0.035 (2) | 0.047 (2) | 0.073 (3) | 0.0026 (18) | −0.004 (2) | −0.009 (2) |
C11 | 0.043 (2) | 0.045 (2) | 0.069 (3) | −0.0048 (19) | −0.002 (2) | −0.006 (2) |
C12 | 0.045 (2) | 0.042 (2) | 0.085 (4) | 0.0045 (19) | −0.005 (2) | −0.004 (2) |
C13 | 0.041 (2) | 0.040 (2) | 0.075 (3) | 0.0040 (18) | −0.008 (2) | −0.005 (2) |
C14 | 0.038 (2) | 0.041 (2) | 0.056 (3) | 0.0026 (17) | −0.0028 (18) | −0.010 (2) |
O15 | 0.0430 (15) | 0.0361 (15) | 0.085 (2) | 0.0058 (13) | −0.0048 (15) | −0.0086 (16) |
O16 | 0.0409 (15) | 0.0425 (17) | 0.107 (3) | −0.0043 (13) | 0.0025 (17) | −0.0120 (18) |
O17 | 0.0389 (14) | 0.0475 (17) | 0.0541 (19) | 0.0063 (12) | −0.0050 (13) | −0.0031 (14) |
C18 | 0.037 (2) | 0.043 (2) | 0.055 (3) | 0.0050 (17) | −0.0051 (19) | −0.006 (2) |
C19 | 0.037 (2) | 0.041 (2) | 0.058 (3) | 0.0024 (17) | 0.0013 (19) | −0.001 (2) |
C20 | 0.038 (2) | 0.040 (2) | 0.054 (3) | 0.0023 (17) | 0.0015 (18) | −0.0023 (19) |
O21 | 0.0514 (17) | 0.0521 (19) | 0.059 (2) | 0.0047 (15) | 0.0018 (15) | −0.0044 (16) |
C22 | 0.037 (2) | 0.046 (2) | 0.055 (3) | 0.0064 (17) | −0.0010 (18) | −0.002 (2) |
C23 | 0.0340 (19) | 0.045 (2) | 0.061 (3) | 0.0011 (17) | −0.0048 (18) | −0.002 (2) |
C24 | 0.044 (2) | 0.046 (2) | 0.056 (3) | −0.0010 (18) | −0.003 (2) | −0.005 (2) |
C25 | 0.038 (2) | 0.051 (3) | 0.057 (3) | 0.0035 (18) | 0.0034 (19) | −0.006 (2) |
N26 | 0.0429 (18) | 0.046 (2) | 0.060 (2) | 0.0064 (16) | −0.0094 (17) | −0.0054 (18) |
C27 | 0.042 (2) | 0.048 (2) | 0.056 (3) | −0.0002 (18) | −0.0078 (19) | 0.002 (2) |
N28 | 0.046 (2) | 0.041 (2) | 0.069 (3) | 0.0028 (16) | −0.0160 (17) | −0.0009 (18) |
S29 | 0.0543 (6) | 0.0454 (6) | 0.0736 (9) | 0.0011 (5) | −0.0144 (6) | −0.0027 (6) |
C30 | 0.050 (2) | 0.039 (2) | 0.063 (3) | 0.0015 (19) | −0.010 (2) | 0.001 (2) |
C31 | 0.044 (2) | 0.051 (3) | 0.082 (4) | 0.004 (2) | −0.007 (2) | 0.000 (3) |
C32 | 0.044 (2) | 0.044 (2) | 0.084 (4) | 0.0012 (19) | −0.005 (2) | −0.003 (2) |
C33 | 0.049 (2) | 0.041 (2) | 0.063 (3) | 0.0012 (19) | −0.006 (2) | −0.005 (2) |
C34 | 0.044 (2) | 0.044 (2) | 0.070 (3) | −0.0028 (18) | −0.006 (2) | 0.004 (2) |
C35 | 0.045 (2) | 0.048 (3) | 0.064 (3) | −0.0009 (19) | −0.005 (2) | 0.009 (2) |
N36 | 0.043 (2) | 0.044 (2) | 0.083 (3) | 0.0023 (16) | −0.0078 (19) | −0.006 (2) |
C37 | 0.050 (2) | 0.046 (3) | 0.063 (3) | −0.002 (2) | −0.009 (2) | −0.010 (2) |
N38 | 0.079 (3) | 0.051 (3) | 0.107 (4) | −0.006 (2) | −0.039 (3) | 0.014 (3) |
C39 | 0.119 (6) | 0.058 (4) | 0.192 (9) | −0.034 (4) | −0.103 (6) | 0.041 (5) |
C40 | 0.108 (5) | 0.062 (4) | 0.170 (8) | −0.029 (4) | −0.081 (5) | 0.039 (4) |
C41 | 0.063 (3) | 0.050 (3) | 0.068 (3) | −0.006 (2) | −0.022 (2) | 0.001 (2) |
C42 | 0.056 (3) | 0.040 (2) | 0.062 (3) | 0.001 (2) | −0.007 (2) | −0.004 (2) |
C43 | 0.055 (3) | 0.047 (2) | 0.057 (3) | −0.004 (2) | −0.007 (2) | 0.009 (2) |
N44 | 0.054 (2) | 0.0402 (19) | 0.058 (2) | −0.0027 (17) | −0.0079 (17) | 0.0009 (18) |
C45 | 0.048 (2) | 0.047 (3) | 0.073 (3) | −0.004 (2) | −0.012 (2) | −0.001 (2) |
N46 | 0.049 (2) | 0.045 (2) | 0.065 (3) | −0.0013 (17) | −0.0119 (18) | −0.0027 (19) |
C47 | 0.056 (3) | 0.047 (3) | 0.061 (3) | −0.006 (2) | −0.007 (2) | −0.002 (2) |
C48 | 0.051 (2) | 0.043 (2) | 0.062 (3) | −0.007 (2) | −0.003 (2) | 0.004 (2) |
C49 | 0.077 (3) | 0.049 (3) | 0.092 (4) | 0.005 (3) | 0.027 (3) | 0.010 (3) |
C50 | 0.080 (4) | 0.046 (3) | 0.116 (5) | −0.005 (3) | 0.029 (4) | 0.011 (3) |
C51 | 0.074 (3) | 0.036 (2) | 0.092 (4) | −0.005 (2) | −0.004 (3) | −0.007 (3) |
C52 | 0.138 (6) | 0.053 (3) | 0.085 (5) | −0.015 (4) | 0.036 (4) | −0.016 (3) |
C53 | 0.133 (6) | 0.053 (3) | 0.069 (4) | −0.027 (3) | 0.033 (4) | −0.011 (3) |
F54 | 0.110 (3) | 0.0416 (17) | 0.130 (3) | −0.0085 (17) | 0.003 (2) | −0.0046 (18) |
C1L | 0.151 (8) | 0.113 (6) | 0.108 (7) | 0.029 (6) | 0.026 (6) | 0.039 (5) |
O1L | 0.099 (6) | 0.122 (7) | 0.111 (7) | 0.036 (5) | −0.006 (5) | 0.026 (6) |
O2L | 0.108 (8) | 0.052 (6) | 0.086 (7) | 0.018 (5) | 0.027 (6) | 0.007 (5) |
C1—C2 | 1.501 (6) | C31—H31 | 0.9500 |
C1—C14 | 1.503 (6) | C32—C33 | 1.395 (6) |
C1—C20 | 1.511 (6) | C32—H32 | 0.9500 |
C1—O17 | 1.527 (5) | C33—C34 | 1.394 (6) |
C2—C7 | 1.383 (5) | C33—N36 | 1.404 (6) |
C2—C3 | 1.385 (6) | C34—C35 | 1.374 (6) |
C3—C4 | 1.376 (6) | C34—H34 | 0.9500 |
C3—H3 | 0.9500 | C35—H35 | 0.9500 |
C4—C5 | 1.403 (6) | N36—C37 | 1.371 (6) |
C4—H4 | 0.9500 | N36—H36 | 0.8800 |
C5—O15 | 1.347 (5) | C37—N38 | 1.348 (6) |
C5—C6 | 1.380 (6) | C37—C42 | 1.400 (6) |
C6—C7 | 1.386 (6) | N38—C39 | 1.322 (7) |
C6—H6 | 0.9500 | C39—C40 | 1.368 (9) |
C7—O8 | 1.383 (5) | C39—H39 | 0.9500 |
O8—C9 | 1.382 (5) | C40—C41 | 1.385 (8) |
C9—C10 | 1.377 (6) | C40—H40 | 0.9500 |
C9—C14 | 1.385 (6) | C41—C42 | 1.375 (6) |
C10—C11 | 1.387 (6) | C41—C43 | 1.462 (7) |
C10—H10 | 0.9500 | C42—H42 | 0.9500 |
C11—O16 | 1.354 (5) | C43—C47 | 1.373 (6) |
C11—C12 | 1.389 (6) | C43—N44 | 1.388 (6) |
C12—C13 | 1.378 (6) | N44—C45 | 1.354 (6) |
C12—H12 | 0.9500 | N44—C48 | 1.423 (6) |
C13—C14 | 1.393 (6) | C45—N46 | 1.314 (6) |
C13—H13 | 0.9500 | C45—H45 | 0.9500 |
O15—H15 | 0.8400 | N46—C47 | 1.353 (6) |
O16—H16 | 0.8400 | C47—H47 | 0.9500 |
O17—C18 | 1.354 (5) | C48—C53 | 1.358 (7) |
C18—O21 | 1.223 (5) | C48—C49 | 1.360 (7) |
C18—C19 | 1.456 (7) | C49—C50 | 1.389 (7) |
C19—C20 | 1.381 (6) | C49—H49 | 0.9500 |
C19—C22 | 1.392 (6) | C50—C51 | 1.333 (8) |
C20—C25 | 1.372 (7) | C50—H50 | 0.9500 |
C22—C23 | 1.376 (6) | C51—C52 | 1.358 (8) |
C22—H22 | 0.9500 | C51—F54 | 1.365 (6) |
C23—C24 | 1.402 (6) | C52—C53 | 1.376 (8) |
C23—N26 | 1.429 (5) | C52—H52 | 0.9500 |
C24—C25 | 1.384 (6) | C53—H53 | 0.9500 |
C24—H24 | 0.9500 | C1L—O1L | 1.3998 (10) |
C25—H25 | 0.9500 | C1L—O2L | 1.4009 (10) |
N26—C27 | 1.362 (6) | C1L—H1M | 0.9800 |
N26—H26 | 1.0913 | C1L—H2M | 0.9800 |
C27—N28 | 1.350 (6) | C1L—H3M | 0.9800 |
C27—S29 | 1.675 (5) | C1L—H4M | 0.9800 |
N28—C30 | 1.434 (6) | C1L—H5M | 0.9800 |
N28—H28 | 1.1665 | C1L—H6M | 0.9800 |
C30—C35 | 1.383 (6) | O1L—H1L | 0.8400 |
C30—C31 | 1.389 (6) | O2L—H2L | 0.8400 |
C31—C32 | 1.386 (7) | ||
C2—C1—C14 | 112.1 (3) | C32—C31—C30 | 121.3 (4) |
C2—C1—C20 | 113.8 (4) | C32—C31—H31 | 119.4 |
C14—C1—C20 | 113.9 (4) | C30—C31—H31 | 119.4 |
C2—C1—O17 | 108.1 (4) | C31—C32—C33 | 119.8 (4) |
C14—C1—O17 | 107.2 (3) | C31—C32—H32 | 120.1 |
C20—C1—O17 | 100.8 (3) | C33—C32—H32 | 120.1 |
C7—C2—C3 | 117.3 (4) | C34—C33—C32 | 118.6 (4) |
C7—C2—C1 | 120.9 (4) | C34—C33—N36 | 116.8 (4) |
C3—C2—C1 | 121.8 (3) | C32—C33—N36 | 124.3 (4) |
C4—C3—C2 | 122.4 (4) | C35—C34—C33 | 120.7 (4) |
C4—C3—H3 | 118.8 | C35—C34—H34 | 119.6 |
C2—C3—H3 | 118.8 | C33—C34—H34 | 119.6 |
C3—C4—C5 | 119.2 (4) | C34—C35—C30 | 121.1 (4) |
C3—C4—H4 | 120.4 | C34—C35—H35 | 119.5 |
C5—C4—H4 | 120.4 | C30—C35—H35 | 119.5 |
O15—C5—C6 | 118.0 (4) | C37—N36—C33 | 132.1 (4) |
O15—C5—C4 | 122.8 (4) | C37—N36—H36 | 114.0 |
C6—C5—C4 | 119.2 (4) | C33—N36—H36 | 114.0 |
C5—C6—C7 | 120.0 (4) | N38—C37—N36 | 112.7 (4) |
C5—C6—H6 | 120.0 | N38—C37—C42 | 122.5 (4) |
C7—C6—H6 | 120.0 | N36—C37—C42 | 124.7 (4) |
O8—C7—C2 | 123.3 (4) | C39—N38—C37 | 116.0 (5) |
O8—C7—C6 | 115.0 (3) | N38—C39—C40 | 124.8 (6) |
C2—C7—C6 | 121.8 (4) | N38—C39—H39 | 117.6 |
C9—O8—C7 | 118.5 (3) | C40—C39—H39 | 117.6 |
C10—C9—O8 | 115.4 (4) | C39—C40—C41 | 119.7 (6) |
C10—C9—C14 | 122.2 (4) | C39—C40—H40 | 120.1 |
O8—C9—C14 | 122.5 (4) | C41—C40—H40 | 120.1 |
C9—C10—C11 | 119.5 (4) | C42—C41—C40 | 116.5 (5) |
C9—C10—H10 | 120.2 | C42—C41—C43 | 126.9 (4) |
C11—C10—H10 | 120.2 | C40—C41—C43 | 116.5 (4) |
O16—C11—C12 | 122.6 (4) | C41—C42—C37 | 120.1 (4) |
O16—C11—C10 | 117.8 (4) | C41—C42—H42 | 119.9 |
C12—C11—C10 | 119.6 (4) | C37—C42—H42 | 119.9 |
C13—C12—C11 | 119.7 (4) | C47—C43—N44 | 104.1 (4) |
C13—C12—H12 | 120.2 | C47—C43—C41 | 126.7 (4) |
C11—C12—H12 | 120.2 | N44—C43—C41 | 129.1 (4) |
C12—C13—C14 | 121.7 (4) | C45—N44—C43 | 107.0 (4) |
C12—C13—H13 | 119.1 | C45—N44—C48 | 121.2 (4) |
C14—C13—H13 | 119.1 | C43—N44—C48 | 131.5 (4) |
C9—C14—C13 | 117.3 (4) | N46—C45—N44 | 112.0 (4) |
C9—C14—C1 | 121.4 (4) | N46—C45—H45 | 124.0 |
C13—C14—C1 | 121.2 (4) | N44—C45—H45 | 124.0 |
C5—O15—H15 | 109.5 | C45—N46—C47 | 105.2 (4) |
C11—O16—H16 | 109.5 | N46—C47—C43 | 111.6 (4) |
C18—O17—C1 | 110.7 (3) | N46—C47—H47 | 124.2 |
O21—C18—O17 | 120.9 (4) | C43—C47—H47 | 124.2 |
O21—C18—C19 | 130.0 (4) | C53—C48—C49 | 119.9 (5) |
O17—C18—C19 | 109.1 (4) | C53—C48—N44 | 119.1 (4) |
C20—C19—C22 | 122.0 (4) | C49—C48—N44 | 120.8 (5) |
C20—C19—C18 | 108.7 (4) | C48—C49—C50 | 120.2 (5) |
C22—C19—C18 | 129.4 (4) | C48—C49—H49 | 119.9 |
C25—C20—C19 | 120.7 (4) | C50—C49—H49 | 119.9 |
C25—C20—C1 | 129.0 (4) | C51—C50—C49 | 118.3 (5) |
C19—C20—C1 | 110.2 (4) | C51—C50—H50 | 120.9 |
C23—C22—C19 | 117.1 (4) | C49—C50—H50 | 120.9 |
C23—C22—H22 | 121.4 | C50—C51—C52 | 123.1 (5) |
C19—C22—H22 | 121.4 | C50—C51—F54 | 119.1 (5) |
C22—C23—C24 | 121.2 (4) | C52—C51—F54 | 117.8 (5) |
C22—C23—N26 | 118.0 (4) | C51—C52—C53 | 118.0 (6) |
C24—C23—N26 | 120.6 (4) | C51—C52—H52 | 121.0 |
C25—C24—C23 | 120.5 (5) | C53—C52—H52 | 121.0 |
C25—C24—H24 | 119.7 | C48—C53—C52 | 120.6 (5) |
C23—C24—H24 | 119.7 | C48—C53—H53 | 119.7 |
C20—C25—C24 | 118.5 (4) | C52—C53—H53 | 119.7 |
C20—C25—H25 | 120.7 | O1L—C1L—H1M | 109.5 |
C24—C25—H25 | 120.7 | O1L—C1L—H2M | 109.5 |
C27—N26—C23 | 127.3 (4) | H1M—C1L—H2M | 109.5 |
C27—N26—H26 | 126.1 | O1L—C1L—H3M | 109.5 |
C23—N26—H26 | 106.1 | H1M—C1L—H3M | 109.5 |
N28—C27—N26 | 114.8 (4) | H2M—C1L—H3M | 109.5 |
N28—C27—S29 | 121.2 (4) | O2L—C1L—H4M | 109.5 |
N26—C27—S29 | 124.0 (3) | O2L—C1L—H5M | 109.5 |
C27—N28—C30 | 125.9 (4) | H4M—C1L—H5M | 109.5 |
C27—N28—H28 | 107.4 | O2L—C1L—H6M | 109.5 |
C30—N28—H28 | 126.4 | H4M—C1L—H6M | 109.5 |
C35—C30—C31 | 118.4 (4) | H5M—C1L—H6M | 109.5 |
C35—C30—N28 | 119.6 (4) | C1L—O1L—H1L | 109.5 |
C31—C30—N28 | 121.8 (4) | C1L—O2L—H2L | 109.5 |
C14—C1—C2—C7 | 7.2 (6) | C22—C23—C24—C25 | −2.0 (7) |
C20—C1—C2—C7 | 138.2 (4) | N26—C23—C24—C25 | 172.5 (4) |
O17—C1—C2—C7 | −110.7 (4) | C19—C20—C25—C24 | 0.7 (7) |
C14—C1—C2—C3 | −172.6 (4) | C1—C20—C25—C24 | −174.6 (4) |
C20—C1—C2—C3 | −41.6 (6) | C23—C24—C25—C20 | 0.7 (7) |
O17—C1—C2—C3 | 69.5 (5) | C22—C23—N26—C27 | −142.2 (5) |
C7—C2—C3—C4 | −1.7 (7) | C24—C23—N26—C27 | 43.1 (7) |
C1—C2—C3—C4 | 178.1 (5) | C23—N26—C27—N28 | −166.0 (4) |
C2—C3—C4—C5 | −1.6 (8) | C23—N26—C27—S29 | 16.3 (7) |
C3—C4—C5—O15 | −175.9 (5) | N26—C27—N28—C30 | 20.6 (7) |
C3—C4—C5—C6 | 3.8 (7) | S29—C27—N28—C30 | −161.7 (4) |
O15—C5—C6—C7 | 177.1 (4) | C27—N28—C30—C35 | −141.9 (5) |
C4—C5—C6—C7 | −2.7 (7) | C27—N28—C30—C31 | 43.5 (7) |
C3—C2—C7—O8 | −177.0 (4) | C35—C30—C31—C32 | −1.6 (8) |
C1—C2—C7—O8 | 3.2 (7) | N28—C30—C31—C32 | 173.1 (5) |
C3—C2—C7—C6 | 2.9 (7) | C30—C31—C32—C33 | −0.1 (9) |
C1—C2—C7—C6 | −176.9 (5) | C31—C32—C33—C34 | 0.6 (8) |
C5—C6—C7—O8 | 179.2 (4) | C31—C32—C33—N36 | −173.1 (5) |
C5—C6—C7—C2 | −0.7 (8) | C32—C33—C34—C35 | 0.6 (8) |
C2—C7—O8—C9 | −9.8 (7) | N36—C33—C34—C35 | 174.7 (5) |
C6—C7—O8—C9 | 170.3 (4) | C33—C34—C35—C30 | −2.4 (8) |
C7—O8—C9—C10 | −174.6 (4) | C31—C30—C35—C34 | 2.8 (8) |
C7—O8—C9—C14 | 4.9 (7) | N28—C30—C35—C34 | −172.0 (5) |
O8—C9—C10—C11 | 178.0 (5) | C34—C33—N36—C37 | 165.4 (5) |
C14—C9—C10—C11 | −1.5 (8) | C32—C33—N36—C37 | −20.9 (9) |
C9—C10—C11—O16 | −179.7 (4) | C33—N36—C37—N38 | 165.5 (5) |
C9—C10—C11—C12 | −0.6 (8) | C33—N36—C37—C42 | −18.5 (9) |
O16—C11—C12—C13 | −178.9 (5) | N36—C37—N38—C39 | 176.4 (7) |
C10—C11—C12—C13 | 2.0 (8) | C42—C37—N38—C39 | 0.3 (9) |
C11—C12—C13—C14 | −1.5 (8) | C37—N38—C39—C40 | 4.4 (14) |
C10—C9—C14—C13 | 2.0 (7) | N38—C39—C40—C41 | −6.7 (16) |
O8—C9—C14—C13 | −177.5 (4) | C39—C40—C41—C42 | 4.0 (12) |
C10—C9—C14—C1 | −174.3 (5) | C39—C40—C41—C43 | −173.0 (8) |
O8—C9—C14—C1 | 6.2 (7) | C40—C41—C42—C37 | 0.3 (9) |
C12—C13—C14—C9 | −0.5 (8) | C43—C41—C42—C37 | 176.9 (5) |
C12—C13—C14—C1 | 175.8 (5) | N38—C37—C42—C41 | −2.5 (8) |
C2—C1—C14—C9 | −11.7 (6) | N36—C37—C42—C41 | −178.2 (5) |
C20—C1—C14—C9 | −142.7 (4) | C42—C41—C43—C47 | −162.3 (5) |
O17—C1—C14—C9 | 106.7 (5) | C40—C41—C43—C47 | 14.3 (9) |
C2—C1—C14—C13 | 172.1 (4) | C42—C41—C43—N44 | 16.3 (9) |
C20—C1—C14—C13 | 41.2 (6) | C40—C41—C43—N44 | −167.1 (6) |
O17—C1—C14—C13 | −69.4 (5) | C47—C43—N44—C45 | −0.4 (5) |
C2—C1—O17—C18 | −127.2 (4) | C41—C43—N44—C45 | −179.2 (5) |
C14—C1—O17—C18 | 111.8 (4) | C47—C43—N44—C48 | −173.9 (5) |
C20—C1—O17—C18 | −7.6 (4) | C41—C43—N44—C48 | 7.3 (9) |
C1—O17—C18—O21 | −173.6 (4) | C43—N44—C45—N46 | 1.1 (6) |
C1—O17—C18—C19 | 6.0 (5) | C48—N44—C45—N46 | 175.4 (4) |
O21—C18—C19—C20 | 178.0 (5) | N44—C45—N46—C47 | −1.3 (6) |
O17—C18—C19—C20 | −1.5 (5) | C45—N46—C47—C43 | 1.1 (6) |
O21—C18—C19—C22 | −0.8 (8) | N44—C43—C47—N46 | −0.4 (6) |
O17—C18—C19—C22 | 179.6 (4) | C41—C43—C47—N46 | 178.5 (5) |
C22—C19—C20—C25 | −0.7 (7) | C45—N44—C48—C53 | −79.0 (7) |
C18—C19—C20—C25 | −179.6 (4) | C43—N44—C48—C53 | 93.6 (7) |
C22—C19—C20—C1 | 175.4 (4) | C45—N44—C48—C49 | 94.7 (6) |
C18—C19—C20—C1 | −3.6 (5) | C43—N44—C48—C49 | −92.6 (7) |
C2—C1—C20—C25 | −62.3 (6) | C53—C48—C49—C50 | −1.1 (9) |
C14—C1—C20—C25 | 67.8 (6) | N44—C48—C49—C50 | −174.8 (5) |
O17—C1—C20—C25 | −177.8 (4) | C48—C49—C50—C51 | 0.0 (10) |
C2—C1—C20—C19 | 122.1 (4) | C49—C50—C51—C52 | 1.6 (11) |
C14—C1—C20—C19 | −107.8 (4) | C49—C50—C51—F54 | −179.2 (6) |
O17—C1—C20—C19 | 6.6 (4) | C50—C51—C52—C53 | −2.0 (11) |
C20—C19—C22—C23 | −0.6 (6) | F54—C51—C52—C53 | 178.8 (6) |
C18—C19—C22—C23 | 178.1 (4) | C49—C48—C53—C52 | 0.7 (10) |
C19—C22—C23—C24 | 1.9 (6) | N44—C48—C53—C52 | 174.5 (6) |
C19—C22—C23—N26 | −172.8 (4) | C51—C52—C53—C48 | 0.7 (11) |
D—H···A | D—H | H···A | D···A | D—H···A |
O15—H15···N46i | 0.84 | 1.84 | 2.667 (5) | 168 |
O16—H16···O21ii | 0.84 | 2.04 | 2.808 (5) | 153 |
C22—H22···O15iii | 0.95 | 2.59 | 3.315 (5) | 133 |
C24—H24···S29iv | 0.95 | 2.99 | 3.804 (5) | 145 |
N26—H26···O15iii | 1.09 | 2.17 | 3.061 (5) | 138 |
N28—H28···N38v | 1.17 | 1.94 | 3.069 (6) | 162 |
C34—H34···O1Lvi | 0.95 | 2.46 | 3.334 (9) | 154 |
N36—H36···S29vii | 0.88 | 2.64 | 3.437 (4) | 152 |
C40—H40···O2Lviii | 0.95 | 2.32 | 3.103 (12) | 139 |
C45—H45···O17ii | 0.95 | 2.49 | 3.379 (6) | 155 |
C53—H53···S29ix | 0.95 | 2.87 | 3.743 (6) | 153 |
C1L—H2M···O21 | 0.98 | 2.56 | 3.267 (7) | 129 |
O1L—H1L···S29x | 0.84 | 2.46 | 3.202 (8) | 147 |
Symmetry codes: (i) x, y−1, z; (ii) −x+3/2, −y+1/2, −z+1; (iii) x−1/2, y+1/2, z; (iv) −x+1, y, −z+1/2; (v) −x+1/2, y−1/2, −z+1/2; (vi) −x+1/2, −y+1/2, −z+1; (vii) −x+1/2, y+1/2, −z+1/2; (viii) −x+1, −y+1, −z+1; (ix) x+1/2, y+1/2, z; (x) −x+1, −y, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O15—H15···N46i | 0.84 | 1.84 | 2.667 (5) | 168 |
O16—H16···O21ii | 0.84 | 2.04 | 2.808 (5) | 153 |
C22—H22···O15iii | 0.95 | 2.59 | 3.315 (5) | 133 |
C24—H24···S29iv | 0.95 | 2.99 | 3.804 (5) | 145 |
N26—H26···O15iii | 1.09 | 2.17 | 3.061 (5) | 138 |
N28—H28···N38v | 1.17 | 1.94 | 3.069 (6) | 162 |
C34—H34···O1Lvi | 0.95 | 2.46 | 3.334 (9) | 154 |
N36—H36···S29vii | 0.88 | 2.64 | 3.437 (4) | 152 |
C40—H40···O2Lviii | 0.95 | 2.32 | 3.103 (12) | 139 |
C45—H45···O17ii | 0.95 | 2.49 | 3.379 (6) | 155 |
C53—H53···S29ix | 0.95 | 2.87 | 3.743 (6) | 153 |
C1L—H2M···O21 | 0.98 | 2.56 | 3.267 (7) | 129 |
O1L—H1L···S29x | 0.84 | 2.46 | 3.202 (8) | 147 |
Symmetry codes: (i) x, y−1, z; (ii) −x+3/2, −y+1/2, −z+1; (iii) x−1/2, y+1/2, z; (iv) −x+1, y, −z+1/2; (v) −x+1/2, y−1/2, −z+1/2; (vi) −x+1/2, −y+1/2, −z+1; (vii) −x+1/2, y+1/2, −z+1/2; (viii) −x+1, −y+1, −z+1; (ix) x+1/2, y+1/2, z; (x) −x+1, −y, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C41H27FN6O5S·CH4O |
Mr | 766.79 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 193 |
a, b, c (Å) | 15.1825 (8), 17.7557 (7), 26.2236 (13) |
β (°) | 92.283 (4) |
V (Å3) | 7063.6 (6) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.16 |
Crystal size (mm) | 0.09 × 0.08 × 0.07 |
Data collection | |
Diffractometer | Stoe IPDS 2T |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 23065, 8960, 3244 |
Rint | 0.085 |
(sin θ/λ)max (Å−1) | 0.674 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.070, 0.240, 0.92 |
No. of reflections | 8960 |
No. of parameters | 516 |
No. of restraints | 2 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.35, −0.38 |
Computer programs: X-AREA (Stoe & Cie, 2011), X-AREA (Stoe & Cie, 2011, X-RED (Stoe & Cie, 2011, SIR2004 (Burla et al., 2005), SHELXL2014 (Sheldrick, 2015).
References
Ansideri, F., Lange, A., El-Gokha, A., Boeckler, F. M. & Koch, P. (2016). Anal. Biochem. 503, 28–40. CrossRef CAS PubMed Google Scholar
Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381–388. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Stoe & Cie (2011). X-RED and X-AREA. Stoe & Cie, Darmstadt, Darmstadt, Germany. Google Scholar
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