organic compounds
N′-[(E)-2-Hydroxybenzylidene]-2-(6-methoxynaphthalen-2-yl)propanohydrazide: a redetermination
aChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England, bChemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt, cDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA, dDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, eNational Organization for Drug Control and Research NODCAR, Giza, Egypt, and fKirkuk University, College of Science, Department of Chemistry, Kirkuk, Iraq
*Correspondence e-mail: shaabankamel@yahoo.com
The structure of the title compound, C21H20N2O3, was originally determined at ambient temperature [Wu et al. (2007). Inorg. Chim. Acta, 360, 3069–3074]. In this determination, with data collected at 150 K, the comprises two independent molecules (1 and 2) that differ considerably in their conformations. In particular, the methyl group at the mid-point of molecule 2 is disordered over two sites. This was modelled with restraints so that the geometries of the two components are comparable and the disorder components refined to an occupancy ratio of 0.750 (6):0.250 (6). Intramolecular O—H⋯N and intermolecular N—H⋯O hydrogen bonds stabilize the structure with significant additional input from C—H⋯π interactions.
CCDC reference: 1474960
Structure description
Non-steroidal anti-inflammatory drugs (NSAIDs) are among the most widely used therapeutic agents. They are very effective in the alleviation of pain, fever and inflammation (Meek et al., 2010; Batlouni, 2010). Naproxen, (+)-(S)-2-(6-methoxynaphthalen-2-yl)propanoic acid, is often used for the treatment of acute and chronic inflammation conditions, musculoskeletal disorders, primary dysmenorrhoea, fever and also in the management of mild pain (Capone et al., 2007; Assali et al., 2014). The structure of the title compound, in which the 6-methoxynaphthalene moiety is closely related to the naproxen molecule, has been determined previously at ambient temperature (Wu et al., 2007) but this article did not address the possibility of pseudo-symmetry in the structure, the disorder in one of the unique molecules or the presence of significant C—H⋯π interactions in the crystal structure.
Although complicated by β angle very close to 90° rather than orthorhombic on the basis of lower merging R values for equivalent reflections and a more satisfactory Moreover, with two molecules in the shows that the C10 methyl group in molecule 1 is disordered over two sites with a 0.750 (6):0.250 (6) occupancy ratio while molecule 2 is completely ordered so that the two molecules are not identical. In molecule 1, the dihedral angle between the phenyl and naphthyl groups is 79.90 (8)° while in molecule 2 it is 82.66 (8)°. The two naphthyl groups are inclined at an angle of 38.51 (8)°. The conformations of both molecules are partially determined by intramolecular O—H⋯N hydrogen bonds while the two molecules in the are associated through an N4—H4N⋯O2 hydrogen bond (Table 1 and Fig. 1). The is further stabilized by three C—H⋯π hydrogen bonds (Table 1). C21—H21A⋯Cg1 interactions link type 1 molecules into chains along c, while C42—H42A⋯Cg4 contacts form parallel chains in an obverse fashion, Fig. 2 (Cg1 and Cg4 are the centroids of the hydroxyphenyl rings of molecules 1 and 2, respectively). The chains are linked by the N4—H4N⋯O2 hydrogen bonds and these pairs of chains are further interconnected by N2—H2N⋯O5 hydrogen bonds, supported by C6—H6⋯Cg6 contacts, forming sheets of molecules in the ac plane (Cg6 is the centroid of the C35–C39 ring in molecule 2).
it is felt that the correct is monoclinic with aSynthesis and crystallization
A mixture of 1 mmol (244 mg) of 2-(6-methoxynaphthalen-2-yl)propanehydrazide and 1 mmol (122 mg) of salicaldehyde with a few drops of glacial acetic acid was refluxed in 20 ml of absolute ethanol for 6 h. The mixture was cooled and the excess solvent evaporated. The solid was filtered off, dried and recrystallized from ethanol to afford yellow crystals of quality suitable for X-ray diffraction with m.p 442–445 K.
Refinement
Crystal data, data collection and structure . In the final stages of the it became evident that C10 was disordered over two sets of sites. This was modelled with restraints to ensure that the geometries of the two components were comparable and the occupancy factors refined to a ratio of 0.750 (6):0.250 (6).
details are summarized in Table 2
|
Structural data
CCDC reference: 1474960
10.1107/S2414314616006623/sj4025sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2414314616006623/sj4025Isup2.hkl
Supporting information file. DOI: 10.1107/S2414314616006623/sj4025Isup3.cml
A mixture of 1 mmol (244mg) of 2-(6-methoxynaphthalen-2-yl)propanehydrazide and 1 mmol (122 mg) of salicaldehyde with few drops of glacial acetic acid was refluxed in 20 mL of absolute ethanol for 6 hr . The mixture was cooled and the excess solvent evaporated. The solid was filtered off, dried and recrystallized from ethanol to afford yellow crystals of quality suitable for X-ray diffraction with m.p 442-445 K.
Crystal data, data collection and structure
details are summarized in Table 2. In the final stages of the it became evident that C10 was disordered over two sites. This was modelled with restraints to ensure that the geometries of the two components were comparable and the occupancy factors refined to a ratio of 0.750 (6):0.250 (6).A mixture of 1 mmol (244 mg) of 2-(6-methoxynaphthalen-2-yl)propanehydrazide and 1 mmol (122 mg) of salicaldehyde with a few drops of glacial acetic acid was refluxed in 20 ml of absolute ethanol for 6 h. The mixture was cooled and the excess solvent evaporated. The solid was filtered off, dried and recrystallized from ethanol to afford yellow crystals of quality suitable for X-ray diffraction with m.p 442–445 K.
Crystal data, data collection and structure
details are summarized in Table 2. In the final stages of the it became evident that C10 was disordered over two sets of sites. This was modelled with restraints to ensure that the geometries of the two components were comparable and the occupancy factors refined to a ratio of 0.750 (6):0.250 (6).Non-steroidal anti-inflammatory drugs (NSAIDs) are among the most widely used therapeutic agents. They are very effective in the alleviation of pain, fever and inflammation (Meek et al., 2010; Batlouni, 2010). Naproxen, (+)-(S)-2-(6-methoxynaphthalen-2-yl)propanoic acid, is often used for the treatment of acute and chronic inflammation conditions, musculoskeletal disorders, primary dysmenorrhoea, fever and also in the management of mild pain (Capone et al., 2007; Assali et al., 2014). The structure of the title compound, in which the 6-methoxynaphthalene moiety is closely related to the naproxen molecule, has been determined previously at ambient temperature (Wu et al., 2007) but this article did not address the possibility of pseudo-symmetry in the structure, the disorder in one of the unique molecules or the presence of significant C—H···π interactions in the crystal structure.
Although complicated by β angle very close to 90° rather than orthorhombic on the basis of lower merging R values for equivalent reflections and a more satisfactory Moreover, with two molecules in the shows that the C10 methyl group in molecule 1 is disordered over two sites with a 0.750 (6):0.250 (6) occupancy ratio while molecule 2 is completely ordered so that the two molecules are not identical. In molecule 1, the dihedral angle between the phenyl and naphthyl groups is 79.90 (8)° while in molecule 2 it is 82.66 (8)°. The two naphthyl groups are inclined at an angle of 38.51 (8)°. The conformations of both molecules are partially determined by intramolecular O—H···N hydrogen bonds while the two molecules in the are associated through an N4—H4N···O2 hydrogen bond (Table 1 and Fig. 1). The is further stabilized by three C—H···π hydrogen bonds (Table 1). C21—H21A···Cg1 interactions link type 1 molecules into chains along c, while C42—H42A···Cg4 contacts form parallel chains in an obverse fashion, Fig. 2 (Cg1 and Cg4 are the centroids of the hydroxyphenyl rings of molecules 1 and 2, respectively). The chains are linked by the N4—H4N···O2 hydrogen bonds and these pairs of chains are further interconnected by N2—H2N···O5 hydrogen bonds, supported by C6—H6···Cg6 contacts, forming sheets of molecules in the ac plane (Cg6 is the centroid of the C35–C39 ring in molecule 2).
it is felt that the correct is monoclinic with aData collection: APEX3 (Bruker, 2016); cell
SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).Fig. 1. The asymmetric unit with the atom-labeling scheme and 50% probability ellipsoids. Only the major component of the disorder in the C10 methyl group is shown. O—H···N and N—H···O hydrogen bonds are shown, respectively, as red and blue dashed lines. | |
Fig. 2. Sheets of molecules in the ac plane formed by N—H···O hydrogen bonds (blue dashed lines)and C—H···π contacts (green dotted lines). Ring centroids are shown as coloured spheres. |
C21H20N2O3 | F(000) = 736 |
Mr = 348.39 | Dx = 1.276 Mg m−3 |
Monoclinic, P21 | Cu Kα radiation, λ = 1.54178 Å |
a = 9.5461 (5) Å | Cell parameters from 9655 reflections |
b = 11.8724 (6) Å | θ = 4.6–72.4° |
c = 15.9962 (8) Å | µ = 0.70 mm−1 |
β = 90.104 (2)° | T = 150 K |
V = 1812.93 (16) Å3 | Plate, yellow |
Z = 4 | 0.25 × 0.18 × 0.04 mm |
Bruker D8 VENTURE PHOTON 100 CMOS diffractometer | 6487 independent reflections |
Radiation source: INCOATEC IµS micro–focus source | 5685 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.035 |
Detector resolution: 10.4167 pixels mm-1 | θmax = 72.5°, θmin = 4.6° |
ω scans | h = −11→11 |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | k = −14→14 |
Tmin = 0.86, Tmax = 0.97 | l = −19→18 |
14005 measured reflections |
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.042 | w = 1/[σ2(Fo2) + (0.0576P)2 + 0.2712P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.109 | (Δ/σ)max = 0.001 |
S = 1.03 | Δρmax = 0.31 e Å−3 |
6487 reflections | Δρmin = −0.22 e Å−3 |
479 parameters | Extinction correction: SHELXL 2014/7 (Sheldrick, 2015a), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
2 restraints | Extinction coefficient: 0.0036 (5) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack x determined using 2150 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
Secondary atom site location: difference Fourier map | Absolute structure parameter: 0.21 (19) |
C21H20N2O3 | V = 1812.93 (16) Å3 |
Mr = 348.39 | Z = 4 |
Monoclinic, P21 | Cu Kα radiation |
a = 9.5461 (5) Å | µ = 0.70 mm−1 |
b = 11.8724 (6) Å | T = 150 K |
c = 15.9962 (8) Å | 0.25 × 0.18 × 0.04 mm |
β = 90.104 (2)° |
Bruker D8 VENTURE PHOTON 100 CMOS diffractometer | 6487 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | 5685 reflections with I > 2σ(I) |
Tmin = 0.86, Tmax = 0.97 | Rint = 0.035 |
14005 measured reflections |
R[F2 > 2σ(F2)] = 0.042 | H-atom parameters constrained |
wR(F2) = 0.109 | Δρmax = 0.31 e Å−3 |
S = 1.03 | Δρmin = −0.22 e Å−3 |
6487 reflections | Absolute structure: Flack x determined using 2150 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
479 parameters | Absolute structure parameter: 0.21 (19) |
2 restraints |
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. H-atoms attached to carbon were placed in calculated positions (C—H = 0.95 - 1.00 Å) while those attached to nitrogen and oxygen were placed in locations derived from a difference map and their parameters adjusted to give N—H = 0.91 and O—H = 0.87 Å. All were included as riding contributions with isotropic displacement parameters 1.2 - 1.5 times those of the attached atoms. In the final stges of the refinement, it became evident that C10 was disordered over two sites. This was modeled with restraints that the geometries of the two components be comparable and refined to a 3:1 ratio. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O1 | 0.6485 (2) | 0.6624 (2) | 0.34737 (14) | 0.0461 (6) | |
H1O | 0.6721 | 0.6019 | 0.3747 | 0.069* | |
O2 | 0.5976 (2) | 0.4145 (2) | 0.49980 (14) | 0.0457 (6) | |
O3 | 0.6524 (3) | 0.5185 (2) | 1.03109 (14) | 0.0501 (6) | |
N1 | 0.7942 (2) | 0.4900 (2) | 0.39852 (15) | 0.0355 (6) | |
N2 | 0.8194 (2) | 0.4042 (2) | 0.45369 (16) | 0.0384 (6) | |
H2N | 0.9073 | 0.3751 | 0.4579 | 0.046* | |
C1 | 0.8776 (3) | 0.6135 (3) | 0.29323 (19) | 0.0367 (7) | |
C2 | 0.7594 (3) | 0.6842 (3) | 0.29667 (19) | 0.0382 (7) | |
C3 | 0.7558 (4) | 0.7815 (3) | 0.2483 (2) | 0.0463 (8) | |
H3 | 0.6785 | 0.8315 | 0.2528 | 0.056* | |
C4 | 0.8636 (4) | 0.8061 (3) | 0.1937 (2) | 0.0505 (9) | |
H4 | 0.8591 | 0.8721 | 0.1603 | 0.061* | |
C5 | 0.9788 (4) | 0.7345 (3) | 0.1876 (2) | 0.0501 (9) | |
H5 | 1.0521 | 0.7506 | 0.1493 | 0.060* | |
C6 | 0.9854 (3) | 0.6404 (3) | 0.2372 (2) | 0.0440 (8) | |
H6 | 1.0648 | 0.5924 | 0.2336 | 0.053* | |
C7 | 0.8931 (3) | 0.5174 (3) | 0.34828 (19) | 0.0369 (7) | |
H7 | 0.9770 | 0.4744 | 0.3472 | 0.044* | |
C8 | 0.7144 (3) | 0.3729 (3) | 0.50537 (18) | 0.0378 (7) | |
C9 | 0.7485 (5) | 0.2842 (3) | 0.5710 (2) | 0.0533 (10) | 0.750 (6) |
H9 | 0.6630 | 0.2356 | 0.5724 | 0.064* | 0.750 (6) |
C10 | 0.8613 (5) | 0.2058 (4) | 0.5588 (3) | 0.0446 (10) | 0.750 (6) |
H10A | 0.8490 | 0.1672 | 0.5052 | 0.067* | 0.750 (6) |
H10B | 0.8612 | 0.1503 | 0.6042 | 0.067* | 0.750 (6) |
H10C | 0.9506 | 0.2465 | 0.5589 | 0.067* | 0.750 (6) |
C9A | 0.7485 (5) | 0.2842 (3) | 0.5710 (2) | 0.0533 (10) | 0.250 (6) |
H9A | 0.8508 | 0.2720 | 0.5611 | 0.064* | 0.250 (6) |
C10A | 0.6945 (14) | 0.1744 (7) | 0.5570 (8) | 0.0446 (10) | 0.250 (6) |
H10D | 0.5936 | 0.1739 | 0.5681 | 0.067* | 0.250 (6) |
H10E | 0.7414 | 0.1209 | 0.5943 | 0.067* | 0.250 (6) |
H10F | 0.7112 | 0.1526 | 0.4988 | 0.067* | 0.250 (6) |
C11 | 0.7502 (3) | 0.3408 (3) | 0.65668 (18) | 0.0384 (7) | |
C12 | 0.8507 (3) | 0.4254 (3) | 0.6747 (2) | 0.0407 (7) | |
H12 | 0.9166 | 0.4460 | 0.6329 | 0.049* | |
C13 | 0.8551 (3) | 0.4779 (3) | 0.75069 (18) | 0.0371 (7) | |
H13 | 0.9227 | 0.5351 | 0.7606 | 0.045* | |
C14 | 0.7602 (3) | 0.4481 (3) | 0.81483 (18) | 0.0329 (6) | |
C15 | 0.7607 (3) | 0.5016 (3) | 0.89421 (18) | 0.0363 (7) | |
H15 | 0.8275 | 0.5587 | 0.9061 | 0.044* | |
C16 | 0.6650 (3) | 0.4711 (3) | 0.95362 (19) | 0.0386 (7) | |
C17 | 0.5681 (3) | 0.3831 (3) | 0.9375 (2) | 0.0425 (7) | |
H17 | 0.5037 | 0.3610 | 0.9796 | 0.051* | |
C18 | 0.5668 (3) | 0.3303 (3) | 0.86249 (19) | 0.0403 (7) | |
H18 | 0.5015 | 0.2714 | 0.8528 | 0.048* | |
C19 | 0.6611 (3) | 0.3614 (3) | 0.79797 (18) | 0.0341 (6) | |
C20 | 0.6579 (3) | 0.3106 (3) | 0.71823 (19) | 0.0385 (7) | |
H20 | 0.5901 | 0.2541 | 0.7069 | 0.046* | |
C21 | 0.7521 (5) | 0.6018 (4) | 1.0534 (2) | 0.0591 (10) | |
H21A | 0.7346 | 0.6270 | 1.1108 | 0.089* | |
H21B | 0.7440 | 0.6660 | 1.0152 | 0.089* | |
H21C | 0.8466 | 0.5700 | 1.0496 | 0.089* | |
O4 | 0.1372 (2) | 0.6691 (2) | 0.66597 (14) | 0.0467 (6) | |
H4O | 0.1615 | 0.6097 | 0.6376 | 0.070* | |
O5 | 0.1009 (2) | 0.4092 (2) | 0.49733 (14) | 0.0434 (5) | |
O6 | 0.1563 (3) | 0.5107 (2) | −0.03381 (15) | 0.0565 (7) | |
N3 | 0.2906 (2) | 0.5061 (2) | 0.60278 (14) | 0.0346 (5) | |
N4 | 0.3235 (2) | 0.4228 (2) | 0.54634 (16) | 0.0367 (6) | |
H4N | 0.4157 | 0.4041 | 0.5432 | 0.044* | |
C22 | 0.3748 (3) | 0.6290 (3) | 0.70936 (18) | 0.0325 (6) | |
C23 | 0.2518 (3) | 0.6945 (3) | 0.71272 (19) | 0.0362 (7) | |
C24 | 0.2460 (4) | 0.7886 (3) | 0.7648 (2) | 0.0443 (8) | |
H24 | 0.1652 | 0.8355 | 0.7645 | 0.053* | |
C25 | 0.3570 (4) | 0.8139 (3) | 0.8167 (2) | 0.0474 (8) | |
H25 | 0.3518 | 0.8777 | 0.8525 | 0.057* | |
C26 | 0.4768 (4) | 0.7467 (3) | 0.8173 (2) | 0.0460 (8) | |
H26 | 0.5518 | 0.7629 | 0.8545 | 0.055* | |
C27 | 0.4853 (3) | 0.6567 (3) | 0.76323 (19) | 0.0385 (7) | |
H27 | 0.5681 | 0.6123 | 0.7625 | 0.046* | |
C28 | 0.3916 (3) | 0.5368 (3) | 0.65108 (18) | 0.0347 (6) | |
H28 | 0.4787 | 0.4983 | 0.6484 | 0.042* | |
C29 | 0.2252 (3) | 0.3820 (3) | 0.49370 (18) | 0.0347 (7) | |
C30 | 0.2816 (3) | 0.2981 (3) | 0.42970 (19) | 0.0371 (7) | |
H30 | 0.3825 | 0.2840 | 0.4430 | 0.044* | |
C31 | 0.2038 (4) | 0.1867 (3) | 0.4377 (2) | 0.0518 (9) | |
H31A | 0.2411 | 0.1327 | 0.3971 | 0.078* | |
H31B | 0.1038 | 0.1987 | 0.4269 | 0.078* | |
H31C | 0.2163 | 0.1568 | 0.4944 | 0.078* | |
C32 | 0.2738 (3) | 0.3507 (3) | 0.34317 (19) | 0.0334 (6) | |
C33 | 0.1834 (3) | 0.3126 (3) | 0.28257 (18) | 0.0333 (6) | |
H33 | 0.1216 | 0.2521 | 0.2950 | 0.040* | |
C34 | 0.1805 (3) | 0.3619 (3) | 0.20190 (18) | 0.0323 (6) | |
C35 | 0.0885 (3) | 0.3238 (3) | 0.13800 (19) | 0.0370 (7) | |
H35 | 0.0285 | 0.2616 | 0.1488 | 0.044* | |
C36 | 0.0841 (3) | 0.3740 (3) | 0.06201 (19) | 0.0418 (7) | |
H36 | 0.0216 | 0.3469 | 0.0204 | 0.050* | |
C37 | 0.1726 (4) | 0.4669 (3) | 0.0444 (2) | 0.0422 (7) | |
C38 | 0.2655 (3) | 0.5054 (3) | 0.10334 (19) | 0.0389 (7) | |
H38 | 0.3265 | 0.5662 | 0.0906 | 0.047* | |
C39 | 0.2705 (3) | 0.4542 (2) | 0.18322 (19) | 0.0334 (6) | |
C40 | 0.3638 (3) | 0.4918 (3) | 0.2469 (2) | 0.0397 (7) | |
H40 | 0.4259 | 0.5525 | 0.2359 | 0.048* | |
C41 | 0.3649 (3) | 0.4413 (3) | 0.3238 (2) | 0.0398 (7) | |
H41 | 0.4283 | 0.4676 | 0.3653 | 0.048* | |
C42 | 0.2464 (5) | 0.6007 (4) | −0.0567 (3) | 0.0649 (11) | |
H42A | 0.2295 | 0.6211 | −0.1152 | 0.097* | |
H42B | 0.3441 | 0.5772 | −0.0498 | 0.097* | |
H42C | 0.2278 | 0.6659 | −0.0209 | 0.097* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0351 (11) | 0.0595 (15) | 0.0438 (13) | 0.0128 (11) | 0.0022 (9) | −0.0024 (12) |
O2 | 0.0295 (10) | 0.0650 (16) | 0.0425 (12) | 0.0093 (11) | 0.0011 (8) | 0.0095 (11) |
O3 | 0.0633 (15) | 0.0544 (14) | 0.0327 (11) | −0.0122 (13) | 0.0029 (10) | −0.0091 (11) |
N1 | 0.0301 (11) | 0.0451 (14) | 0.0311 (12) | 0.0039 (11) | −0.0035 (9) | −0.0094 (11) |
N2 | 0.0315 (12) | 0.0493 (15) | 0.0343 (13) | 0.0133 (12) | −0.0042 (10) | −0.0042 (12) |
C1 | 0.0293 (14) | 0.0461 (18) | 0.0347 (16) | 0.0018 (13) | −0.0016 (11) | −0.0108 (13) |
C2 | 0.0329 (15) | 0.0471 (18) | 0.0346 (16) | 0.0024 (14) | −0.0037 (12) | −0.0097 (14) |
C3 | 0.0465 (18) | 0.0475 (19) | 0.0447 (19) | 0.0064 (16) | −0.0087 (14) | −0.0106 (16) |
C4 | 0.057 (2) | 0.0446 (19) | 0.050 (2) | −0.0071 (17) | −0.0119 (16) | −0.0052 (17) |
C5 | 0.0445 (18) | 0.055 (2) | 0.050 (2) | −0.0134 (17) | 0.0008 (15) | −0.0055 (18) |
C6 | 0.0346 (16) | 0.052 (2) | 0.0448 (18) | 0.0006 (15) | 0.0018 (13) | −0.0091 (16) |
C7 | 0.0284 (13) | 0.0462 (18) | 0.0361 (15) | 0.0048 (13) | −0.0010 (11) | −0.0102 (14) |
C8 | 0.0395 (16) | 0.0458 (18) | 0.0281 (14) | 0.0067 (14) | −0.0044 (11) | −0.0067 (13) |
C9 | 0.079 (3) | 0.047 (2) | 0.0339 (18) | 0.0216 (19) | −0.0079 (16) | −0.0057 (15) |
C10 | 0.051 (2) | 0.046 (2) | 0.037 (2) | 0.002 (2) | 0.0006 (17) | −0.0022 (18) |
C9A | 0.079 (3) | 0.047 (2) | 0.0339 (18) | 0.0216 (19) | −0.0079 (16) | −0.0057 (15) |
C10A | 0.051 (2) | 0.046 (2) | 0.037 (2) | 0.002 (2) | 0.0006 (17) | −0.0022 (18) |
C11 | 0.0490 (17) | 0.0365 (16) | 0.0298 (15) | 0.0121 (14) | −0.0055 (12) | −0.0014 (13) |
C12 | 0.0442 (16) | 0.0463 (18) | 0.0318 (15) | 0.0101 (15) | 0.0023 (12) | 0.0063 (14) |
C13 | 0.0383 (15) | 0.0389 (16) | 0.0341 (16) | 0.0006 (13) | −0.0021 (12) | 0.0023 (13) |
C14 | 0.0333 (14) | 0.0342 (15) | 0.0313 (15) | 0.0034 (12) | −0.0049 (11) | 0.0022 (12) |
C15 | 0.0391 (15) | 0.0364 (16) | 0.0333 (15) | −0.0017 (13) | −0.0052 (12) | −0.0011 (13) |
C16 | 0.0468 (17) | 0.0391 (17) | 0.0299 (15) | 0.0009 (14) | −0.0044 (12) | −0.0015 (13) |
C17 | 0.0428 (16) | 0.0486 (19) | 0.0361 (16) | −0.0081 (15) | 0.0005 (12) | 0.0009 (15) |
C18 | 0.0412 (16) | 0.0415 (17) | 0.0383 (16) | −0.0072 (14) | −0.0040 (12) | 0.0003 (14) |
C19 | 0.0367 (14) | 0.0342 (15) | 0.0313 (14) | 0.0039 (12) | −0.0063 (11) | −0.0015 (13) |
C20 | 0.0438 (16) | 0.0361 (16) | 0.0357 (16) | 0.0046 (14) | −0.0084 (12) | −0.0002 (14) |
C21 | 0.074 (3) | 0.059 (2) | 0.044 (2) | −0.015 (2) | −0.0021 (18) | −0.0171 (19) |
O4 | 0.0355 (11) | 0.0608 (15) | 0.0438 (13) | 0.0142 (11) | −0.0031 (9) | 0.0045 (12) |
O5 | 0.0269 (10) | 0.0599 (15) | 0.0435 (12) | 0.0003 (10) | −0.0034 (8) | 0.0008 (11) |
O6 | 0.0744 (17) | 0.0602 (16) | 0.0350 (12) | −0.0096 (14) | 0.0013 (11) | 0.0130 (12) |
N3 | 0.0322 (12) | 0.0441 (14) | 0.0274 (12) | −0.0001 (11) | 0.0007 (9) | 0.0000 (11) |
N4 | 0.0293 (11) | 0.0452 (15) | 0.0355 (13) | 0.0012 (11) | −0.0020 (9) | −0.0049 (12) |
C22 | 0.0299 (14) | 0.0357 (15) | 0.0320 (15) | −0.0001 (12) | 0.0012 (11) | 0.0040 (12) |
C23 | 0.0341 (15) | 0.0418 (17) | 0.0326 (16) | 0.0050 (13) | 0.0042 (11) | 0.0108 (13) |
C24 | 0.0498 (18) | 0.0384 (17) | 0.0447 (19) | 0.0088 (15) | 0.0134 (14) | 0.0079 (15) |
C25 | 0.059 (2) | 0.0383 (18) | 0.0445 (18) | −0.0058 (16) | 0.0128 (15) | −0.0007 (15) |
C26 | 0.0453 (18) | 0.0480 (19) | 0.0447 (19) | −0.0107 (16) | 0.0022 (14) | −0.0035 (16) |
C27 | 0.0314 (14) | 0.0425 (17) | 0.0417 (17) | −0.0012 (13) | −0.0007 (12) | 0.0008 (14) |
C28 | 0.0287 (13) | 0.0421 (17) | 0.0333 (15) | 0.0028 (13) | −0.0009 (11) | 0.0004 (13) |
C29 | 0.0327 (14) | 0.0422 (17) | 0.0293 (14) | −0.0040 (13) | −0.0038 (11) | 0.0052 (13) |
C30 | 0.0354 (15) | 0.0381 (16) | 0.0376 (16) | −0.0006 (13) | −0.0058 (12) | −0.0002 (13) |
C31 | 0.073 (2) | 0.0419 (19) | 0.0410 (19) | −0.0109 (18) | −0.0129 (16) | 0.0098 (15) |
C32 | 0.0312 (14) | 0.0331 (15) | 0.0358 (15) | −0.0004 (12) | 0.0015 (11) | 0.0005 (13) |
C33 | 0.0305 (13) | 0.0355 (16) | 0.0339 (15) | −0.0021 (12) | 0.0017 (11) | −0.0011 (13) |
C34 | 0.0306 (13) | 0.0348 (15) | 0.0316 (14) | 0.0006 (12) | 0.0043 (11) | −0.0008 (12) |
C35 | 0.0363 (15) | 0.0400 (17) | 0.0347 (15) | −0.0052 (14) | 0.0014 (11) | −0.0001 (14) |
C36 | 0.0442 (16) | 0.0484 (19) | 0.0329 (15) | −0.0044 (15) | −0.0009 (12) | 0.0004 (14) |
C37 | 0.0493 (18) | 0.0444 (18) | 0.0328 (16) | 0.0028 (15) | 0.0082 (13) | 0.0058 (14) |
C38 | 0.0408 (16) | 0.0368 (16) | 0.0390 (16) | −0.0021 (14) | 0.0081 (12) | 0.0028 (14) |
C39 | 0.0330 (14) | 0.0284 (14) | 0.0387 (16) | 0.0007 (12) | 0.0072 (12) | −0.0002 (12) |
C40 | 0.0387 (15) | 0.0359 (16) | 0.0444 (18) | −0.0073 (14) | 0.0051 (13) | −0.0010 (14) |
C41 | 0.0385 (16) | 0.0412 (17) | 0.0399 (16) | −0.0070 (14) | −0.0010 (13) | −0.0063 (14) |
C42 | 0.084 (3) | 0.060 (3) | 0.050 (2) | −0.012 (2) | 0.008 (2) | 0.025 (2) |
O1—C2 | 1.360 (4) | C21—H21A | 0.9800 |
O1—H1O | 0.8700 | C21—H21B | 0.9800 |
O2—C8 | 1.223 (4) | C21—H21C | 0.9800 |
O3—C16 | 1.367 (4) | O4—C23 | 1.358 (4) |
O3—C21 | 1.417 (5) | O4—H4O | 0.8701 |
N1—C7 | 1.283 (4) | O5—C29 | 1.231 (4) |
N1—N2 | 1.369 (4) | O6—C37 | 1.363 (4) |
N2—C8 | 1.352 (4) | O6—C42 | 1.420 (5) |
N2—H2N | 0.9100 | N3—C28 | 1.287 (4) |
C1—C6 | 1.402 (5) | N3—N4 | 1.375 (4) |
C1—C2 | 1.407 (4) | N4—C29 | 1.349 (4) |
C1—C7 | 1.449 (5) | N4—H4N | 0.9100 |
C2—C3 | 1.390 (5) | C22—C27 | 1.400 (4) |
C3—C4 | 1.382 (6) | C22—C23 | 1.410 (4) |
C3—H3 | 0.9500 | C22—C28 | 1.447 (4) |
C4—C5 | 1.394 (6) | C23—C24 | 1.396 (5) |
C4—H4 | 0.9500 | C24—C25 | 1.378 (5) |
C5—C6 | 1.372 (5) | C24—H24 | 0.9500 |
C5—H5 | 0.9500 | C25—C26 | 1.395 (5) |
C6—H6 | 0.9500 | C25—H25 | 0.9500 |
C7—H7 | 0.9500 | C26—C27 | 1.377 (5) |
C8—C9A | 1.523 (5) | C26—H26 | 0.9500 |
C8—C9 | 1.523 (5) | C27—H27 | 0.9500 |
C9—C10 | 1.436 (6) | C28—H28 | 0.9500 |
C9—C11 | 1.526 (4) | C29—C30 | 1.528 (5) |
C9—H9 | 1.0000 | C30—C32 | 1.520 (4) |
C10—H10A | 0.9800 | C30—C31 | 1.523 (5) |
C10—H10B | 0.9800 | C30—H30 | 1.0000 |
C10—H10C | 0.9800 | C31—H31A | 0.9800 |
C9A—C10A | 1.419 (7) | C31—H31B | 0.9800 |
C9A—C11 | 1.526 (4) | C31—H31C | 0.9800 |
C9A—H9A | 1.0000 | C32—C33 | 1.374 (4) |
C10A—H10D | 0.9800 | C32—C41 | 1.418 (4) |
C10A—H10E | 0.9800 | C33—C34 | 1.417 (4) |
C10A—H10F | 0.9800 | C33—H33 | 0.9500 |
C11—C20 | 1.370 (5) | C34—C35 | 1.421 (4) |
C11—C12 | 1.418 (5) | C34—C39 | 1.425 (4) |
C12—C13 | 1.367 (4) | C35—C36 | 1.354 (4) |
C12—H12 | 0.9500 | C35—H35 | 0.9500 |
C13—C14 | 1.415 (4) | C36—C37 | 1.418 (5) |
C13—H13 | 0.9500 | C36—H36 | 0.9500 |
C14—C15 | 1.420 (4) | C37—C38 | 1.372 (5) |
C14—C19 | 1.424 (4) | C38—C39 | 1.415 (4) |
C15—C16 | 1.368 (5) | C38—H38 | 0.9500 |
C15—H15 | 0.9500 | C39—C40 | 1.423 (4) |
C16—C17 | 1.419 (5) | C40—C41 | 1.368 (5) |
C17—C18 | 1.353 (5) | C40—H40 | 0.9500 |
C17—H17 | 0.9500 | C41—H41 | 0.9500 |
C18—C19 | 1.419 (4) | C42—H42A | 0.9800 |
C18—H18 | 0.9500 | C42—H42B | 0.9800 |
C19—C20 | 1.411 (4) | C42—H42C | 0.9800 |
C20—H20 | 0.9500 | ||
C2—O1—H1O | 104.9 | C11—C20—H20 | 119.2 |
C16—O3—C21 | 117.1 (3) | C19—C20—H20 | 119.2 |
C7—N1—N2 | 117.7 (2) | O3—C21—H21A | 109.5 |
C8—N2—N1 | 118.0 (2) | O3—C21—H21B | 109.5 |
C8—N2—H2N | 122.3 | H21A—C21—H21B | 109.5 |
N1—N2—H2N | 119.4 | O3—C21—H21C | 109.5 |
C6—C1—C2 | 118.6 (3) | H21A—C21—H21C | 109.5 |
C6—C1—C7 | 119.5 (3) | H21B—C21—H21C | 109.5 |
C2—C1—C7 | 121.8 (3) | C23—O4—H4O | 104.6 |
O1—C2—C3 | 118.1 (3) | C37—O6—C42 | 117.1 (3) |
O1—C2—C1 | 122.3 (3) | C28—N3—N4 | 115.2 (2) |
C3—C2—C1 | 119.6 (3) | C29—N4—N3 | 120.6 (2) |
C4—C3—C2 | 120.6 (3) | C29—N4—H4N | 123.4 |
C4—C3—H3 | 119.7 | N3—N4—H4N | 115.7 |
C2—C3—H3 | 119.7 | C27—C22—C23 | 118.3 (3) |
C3—C4—C5 | 120.3 (4) | C27—C22—C28 | 119.4 (3) |
C3—C4—H4 | 119.8 | C23—C22—C28 | 122.4 (3) |
C5—C4—H4 | 119.8 | O4—C23—C24 | 118.3 (3) |
C6—C5—C4 | 119.4 (3) | O4—C23—C22 | 121.8 (3) |
C6—C5—H5 | 120.3 | C24—C23—C22 | 119.9 (3) |
C4—C5—H5 | 120.3 | C25—C24—C23 | 120.2 (3) |
C5—C6—C1 | 121.5 (3) | C25—C24—H24 | 119.9 |
C5—C6—H6 | 119.3 | C23—C24—H24 | 119.9 |
C1—C6—H6 | 119.3 | C24—C25—C26 | 120.6 (3) |
N1—C7—C1 | 120.4 (3) | C24—C25—H25 | 119.7 |
N1—C7—H7 | 119.8 | C26—C25—H25 | 119.7 |
C1—C7—H7 | 119.8 | C27—C26—C25 | 119.3 (3) |
O2—C8—N2 | 121.4 (3) | C27—C26—H26 | 120.4 |
O2—C8—C9A | 121.5 (3) | C25—C26—H26 | 120.4 |
N2—C8—C9A | 117.0 (3) | C26—C27—C22 | 121.6 (3) |
O2—C8—C9 | 121.5 (3) | C26—C27—H27 | 119.2 |
N2—C8—C9 | 117.0 (3) | C22—C27—H27 | 119.2 |
C10—C9—C8 | 120.9 (3) | N3—C28—C22 | 121.2 (3) |
C10—C9—C11 | 113.6 (3) | N3—C28—H28 | 119.4 |
C8—C9—C11 | 108.4 (3) | C22—C28—H28 | 119.4 |
C10—C9—H9 | 104.0 | O5—C29—N4 | 123.0 (3) |
C8—C9—H9 | 104.0 | O5—C29—C30 | 122.9 (3) |
C11—C9—H9 | 104.0 | N4—C29—C30 | 114.0 (2) |
C9—C10—H10A | 109.5 | C32—C30—C31 | 114.2 (3) |
C9—C10—H10B | 109.5 | C32—C30—C29 | 109.0 (3) |
H10A—C10—H10B | 109.5 | C31—C30—C29 | 109.7 (3) |
C9—C10—H10C | 109.5 | C32—C30—H30 | 107.9 |
H10A—C10—H10C | 109.5 | C31—C30—H30 | 107.9 |
H10B—C10—H10C | 109.5 | C29—C30—H30 | 107.9 |
C10A—C9A—C8 | 116.7 (6) | C30—C31—H31A | 109.5 |
C10A—C9A—C11 | 123.4 (6) | C30—C31—H31B | 109.5 |
C8—C9A—C11 | 108.4 (3) | H31A—C31—H31B | 109.5 |
C10A—C9A—H9A | 101.4 | C30—C31—H31C | 109.5 |
C8—C9A—H9A | 101.4 | H31A—C31—H31C | 109.5 |
C11—C9A—H9A | 101.4 | H31B—C31—H31C | 109.5 |
C9A—C10A—H10D | 109.5 | C33—C32—C41 | 118.7 (3) |
C9A—C10A—H10E | 109.5 | C33—C32—C30 | 122.5 (3) |
H10D—C10A—H10E | 109.5 | C41—C32—C30 | 118.8 (3) |
C9A—C10A—H10F | 109.5 | C32—C33—C34 | 121.2 (3) |
H10D—C10A—H10F | 109.5 | C32—C33—H33 | 119.4 |
H10E—C10A—H10F | 109.5 | C34—C33—H33 | 119.4 |
C20—C11—C12 | 118.4 (3) | C33—C34—C35 | 122.3 (3) |
C20—C11—C9 | 121.6 (3) | C33—C34—C39 | 119.9 (3) |
C12—C11—C9 | 120.0 (3) | C35—C34—C39 | 117.8 (3) |
C20—C11—C9A | 121.6 (3) | C36—C35—C34 | 121.6 (3) |
C12—C11—C9A | 120.0 (3) | C36—C35—H35 | 119.2 |
C13—C12—C11 | 121.5 (3) | C34—C35—H35 | 119.2 |
C13—C12—H12 | 119.2 | C35—C36—C37 | 120.2 (3) |
C11—C12—H12 | 119.2 | C35—C36—H36 | 119.9 |
C12—C13—C14 | 120.8 (3) | C37—C36—H36 | 119.9 |
C12—C13—H13 | 119.6 | O6—C37—C38 | 125.2 (3) |
C14—C13—H13 | 119.6 | O6—C37—C36 | 114.3 (3) |
C13—C14—C15 | 122.4 (3) | C38—C37—C36 | 120.5 (3) |
C13—C14—C19 | 118.0 (3) | C37—C38—C39 | 119.9 (3) |
C15—C14—C19 | 119.6 (3) | C37—C38—H38 | 120.0 |
C16—C15—C14 | 120.1 (3) | C39—C38—H38 | 120.0 |
C16—C15—H15 | 119.9 | C38—C39—C40 | 122.1 (3) |
C14—C15—H15 | 119.9 | C38—C39—C34 | 120.0 (3) |
O3—C16—C15 | 125.5 (3) | C40—C39—C34 | 117.9 (3) |
O3—C16—C17 | 114.2 (3) | C41—C40—C39 | 120.7 (3) |
C15—C16—C17 | 120.3 (3) | C41—C40—H40 | 119.7 |
C18—C17—C16 | 120.5 (3) | C39—C40—H40 | 119.7 |
C18—C17—H17 | 119.8 | C40—C41—C32 | 121.7 (3) |
C16—C17—H17 | 119.8 | C40—C41—H41 | 119.2 |
C17—C18—C19 | 121.3 (3) | C32—C41—H41 | 119.2 |
C17—C18—H18 | 119.3 | O6—C42—H42A | 109.5 |
C19—C18—H18 | 119.3 | O6—C42—H42B | 109.5 |
C20—C19—C18 | 122.3 (3) | H42A—C42—H42B | 109.5 |
C20—C19—C14 | 119.5 (3) | O6—C42—H42C | 109.5 |
C18—C19—C14 | 118.2 (3) | H42A—C42—H42C | 109.5 |
C11—C20—C19 | 121.7 (3) | H42B—C42—H42C | 109.5 |
C7—N1—N2—C8 | −178.3 (3) | C12—C11—C20—C19 | 0.0 (4) |
C6—C1—C2—O1 | 178.0 (3) | C9—C11—C20—C19 | 178.7 (3) |
C7—C1—C2—O1 | −4.8 (4) | C9A—C11—C20—C19 | 178.7 (3) |
C6—C1—C2—C3 | −3.5 (4) | C18—C19—C20—C11 | −179.6 (3) |
C7—C1—C2—C3 | 173.7 (3) | C14—C19—C20—C11 | 1.5 (4) |
O1—C2—C3—C4 | −178.0 (3) | C28—N3—N4—C29 | 178.5 (3) |
C1—C2—C3—C4 | 3.5 (5) | C27—C22—C23—O4 | −176.2 (3) |
C2—C3—C4—C5 | −1.1 (5) | C28—C22—C23—O4 | 5.4 (5) |
C3—C4—C5—C6 | −1.2 (5) | C27—C22—C23—C24 | 4.1 (4) |
C4—C5—C6—C1 | 1.1 (5) | C28—C22—C23—C24 | −174.2 (3) |
C2—C1—C6—C5 | 1.2 (5) | O4—C23—C24—C25 | 176.4 (3) |
C7—C1—C6—C5 | −176.0 (3) | C22—C23—C24—C25 | −3.9 (5) |
N2—N1—C7—C1 | −174.8 (3) | C23—C24—C25—C26 | 0.7 (5) |
C6—C1—C7—N1 | −178.4 (3) | C24—C25—C26—C27 | 2.2 (5) |
C2—C1—C7—N1 | 4.5 (4) | C25—C26—C27—C22 | −1.9 (5) |
N1—N2—C8—O2 | 4.7 (4) | C23—C22—C27—C26 | −1.3 (5) |
N1—N2—C8—C9A | −175.0 (3) | C28—C22—C27—C26 | 177.1 (3) |
N1—N2—C8—C9 | −175.0 (3) | N4—N3—C28—C22 | 175.6 (3) |
O2—C8—C9—C10 | 155.7 (4) | C27—C22—C28—N3 | 177.4 (3) |
N2—C8—C9—C10 | −24.6 (5) | C23—C22—C28—N3 | −4.3 (5) |
O2—C8—C9—C11 | −70.5 (4) | N3—N4—C29—O5 | −6.0 (5) |
N2—C8—C9—C11 | 109.2 (3) | N3—N4—C29—C30 | 174.6 (3) |
O2—C8—C9A—C10A | 74.2 (8) | O5—C29—C30—C32 | 68.8 (4) |
N2—C8—C9A—C10A | −106.1 (7) | N4—C29—C30—C32 | −111.8 (3) |
O2—C8—C9A—C11 | −70.5 (4) | O5—C29—C30—C31 | −57.0 (4) |
N2—C8—C9A—C11 | 109.2 (3) | N4—C29—C30—C31 | 122.4 (3) |
C10—C9—C11—C20 | −104.9 (4) | C31—C30—C32—C33 | 11.7 (5) |
C8—C9—C11—C20 | 117.6 (4) | C29—C30—C32—C33 | −111.4 (3) |
C10—C9—C11—C12 | 73.8 (4) | C31—C30—C32—C41 | −167.2 (3) |
C8—C9—C11—C12 | −63.7 (4) | C29—C30—C32—C41 | 69.6 (3) |
C10A—C9A—C11—C20 | −24.2 (8) | C41—C32—C33—C34 | 0.3 (5) |
C8—C9A—C11—C20 | 117.6 (4) | C30—C32—C33—C34 | −178.7 (3) |
C10A—C9A—C11—C12 | 154.5 (7) | C32—C33—C34—C35 | 179.7 (3) |
C8—C9A—C11—C12 | −63.7 (4) | C32—C33—C34—C39 | −1.4 (4) |
C20—C11—C12—C13 | −1.3 (5) | C33—C34—C35—C36 | 178.0 (3) |
C9—C11—C12—C13 | 180.0 (3) | C39—C34—C35—C36 | −0.9 (5) |
C9A—C11—C12—C13 | 180.0 (3) | C34—C35—C36—C37 | 0.0 (5) |
C11—C12—C13—C14 | 1.0 (5) | C42—O6—C37—C38 | 2.4 (5) |
C12—C13—C14—C15 | −179.3 (3) | C42—O6—C37—C36 | −177.2 (3) |
C12—C13—C14—C19 | 0.5 (4) | C35—C36—C37—O6 | −179.0 (3) |
C13—C14—C15—C16 | 178.8 (3) | C35—C36—C37—C38 | 1.4 (5) |
C19—C14—C15—C16 | −1.0 (4) | O6—C37—C38—C39 | 178.6 (3) |
C21—O3—C16—C15 | −3.9 (5) | C36—C37—C38—C39 | −1.8 (5) |
C21—O3—C16—C17 | 175.9 (3) | C37—C38—C39—C40 | −179.3 (3) |
C14—C15—C16—O3 | −178.0 (3) | C37—C38—C39—C34 | 0.9 (5) |
C14—C15—C16—C17 | 2.3 (5) | C33—C34—C39—C38 | −178.5 (3) |
O3—C16—C17—C18 | 178.5 (3) | C35—C34—C39—C38 | 0.4 (4) |
C15—C16—C17—C18 | −1.7 (5) | C33—C34—C39—C40 | 1.7 (4) |
C16—C17—C18—C19 | −0.3 (5) | C35—C34—C39—C40 | −179.4 (3) |
C17—C18—C19—C20 | −177.4 (3) | C38—C39—C40—C41 | 179.3 (3) |
C17—C18—C19—C14 | 1.5 (5) | C34—C39—C40—C41 | −0.9 (5) |
C13—C14—C19—C20 | −1.7 (4) | C39—C40—C41—C32 | −0.2 (5) |
C15—C14—C19—C20 | 178.1 (3) | C33—C32—C41—C40 | 0.5 (5) |
C13—C14—C19—C18 | 179.3 (3) | C30—C32—C41—C40 | 179.6 (3) |
C15—C14—C19—C18 | −0.9 (4) |
Cg1 is the centroid of the hydroxyphenyl ring (C1–C6) of molecule 1; Cg4 and Cg6 are the centroids of the hydroxyphenyl ring (C22–C27) and the benzene ring (C34–C39) of the naphthalene group of molecule 2, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1O···N1 | 0.87 | 1.81 | 2.606 (3) | 151 |
N2—H2N···O5i | 0.91 | 1.99 | 2.776 (3) | 143 |
O4—H4O···N3 | 0.87 | 1.83 | 2.630 (3) | 152 |
N4—H4N···O2 | 0.91 | 1.87 | 2.724 (3) | 154 |
C6—H6···Cg6i | 0.95 | 2.97 | 3.734 (4) | 139 |
C21—H21A···Cg1ii | 0.98 | 2.66 | 3.476 (4) | 141 |
C42—H42A···Cg4iii | 0.98 | 2.62 | 3.403 (5) | 137 |
Symmetry codes: (i) x+1, y, z; (ii) x, y, z+1; (iii) x, y, z−1. |
Cg1 is the centroid of the hydroxyphenyl ring (C1–C6) of molecule 1; Cg4 and Cg6 are the centroids of the hydroxyphenyl ring (C22–C27) and the benzene ring (C34–C39) of the naphthalene group of molecule 2, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1O···N1 | 0.87 | 1.81 | 2.606 (3) | 151 |
N2—H2N···O5i | 0.91 | 1.99 | 2.776 (3) | 143 |
O4—H4O···N3 | 0.87 | 1.83 | 2.630 (3) | 152 |
N4—H4N···O2 | 0.91 | 1.87 | 2.724 (3) | 154 |
C6—H6···Cg6i | 0.95 | 2.97 | 3.734 (4) | 139 |
C21—H21A···Cg1ii | 0.98 | 2.66 | 3.476 (4) | 141 |
C42—H42A···Cg4iii | 0.98 | 2.62 | 3.403 (5) | 137 |
Symmetry codes: (i) x+1, y, z; (ii) x, y, z+1; (iii) x, y, z−1. |
Experimental details
Crystal data | |
Chemical formula | C21H20N2O3 |
Mr | 348.39 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 150 |
a, b, c (Å) | 9.5461 (5), 11.8724 (6), 15.9962 (8) |
β (°) | 90.104 (2) |
V (Å3) | 1812.93 (16) |
Z | 4 |
Radiation type | Cu Kα |
µ (mm−1) | 0.70 |
Crystal size (mm) | 0.25 × 0.18 × 0.04 |
Data collection | |
Diffractometer | Bruker D8 VENTURE PHOTON 100 CMOS |
Absorption correction | Multi-scan (SADABS; Bruker, 2016) |
Tmin, Tmax | 0.86, 0.97 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 14005, 6487, 5685 |
Rint | 0.035 |
(sin θ/λ)max (Å−1) | 0.619 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.042, 0.109, 1.03 |
No. of reflections | 6487 |
No. of parameters | 479 |
No. of restraints | 2 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.31, −0.22 |
Absolute structure | Flack x determined using 2150 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
Absolute structure parameter | 0.21 (19) |
Computer programs: APEX3 (Bruker, 2016), SAINT (Bruker, 2016), SHELXT (Sheldrick, 2015a), SHELXL2014 (Sheldrick, 2015b), DIAMOND (Brandenburg & Putz, 2012) and Mercury (Macrae et al., 2008), SHELXTL (Sheldrick, 2008).
Acknowledgements
The support of NSF–MRI Grant No. 1228232 for the purchase of the diffractometer and Tulane University for support of the Tulane Crystallography Laboratory are gratefully acknowledged.
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