organic compounds
4-Phenyl-5a,6,7,8,9,9a-hexahydro-1H-1,5-benzodiazepin-2(5H)-one
aLaboratoire de Chimie Organique Heterocyclique URAC 21, Av. Ibn Battouta, BP 1014, Faculte des Sciences, Universite Mohammed V, Rabat, Morocco, bLaboratory of Medicinal Chemistry, Drug Sciences Research Center, Faculty of Medicine and Pharmacy, Mohammed V University, Rabat, Morocco, cNational Center of Energy Sciences and Nuclear Techniques, Rabat, Morocco, and dDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA
*Correspondence e-mail: y.ramli@um5s.net.ma
In the title compound, C15H18N2O, the cyclohexyl portion is disordered over two alternate chair conformations in a 0.911 (2):0.089 (2) ratio. In the crystal, inversion-related pairwise N—H⋯O hydrogen bonds form dimers, which are connected into (100) layers by additional N—H⋯O hydrogen bonds.
Keywords: crystal structure; hydrogen bond; benzodiazepine.
CCDC reference: 1855622
Structure description
Benzodiazepines a nowadays well known for their therapeutic virtues. These heterocylic compounds are commonly used as anti-inflammatory (Bhat & Kumar, 2016), antioxidant (Patil et al., 2015) and anticancer (Chen et al., 2014) agents. As part of our studies in this area, we report here the synthesis and structure of a new 1,5-benzodiazepine derivative.
The cyclohexyl ring (C1–C6) in the title molecule (Fig. 1) is disordered over two alternate chair conformations in a 0.911 (2):0.089 (2) ratio. The major component has puckering parameters Q = 0.561 (2) Å, θ = 173.1 (2)° and φ = 321.1 (19)°. A puckering analysis of the major conformation of the seven-membered ring yielded the parameters Q(2) = 0.4234 (19) Å, Q(3) = 0.3884 (18) Å, φ(2) = 123.91 (2)° and φ(3) = 40.0 (3)°, with a total puckering amplitude of 0.574 (2) Å.
In the crystal, inversion-related pairwise N2—H2⋯O1i hydrogen bonds form dimers which are connected into (100) layers by N1—H1B⋯O1ii hydrogen bonds (Table 1 and Fig. 2). These layers have the phenyl rings protruding from both surfaces.
Synthesis and crystallization
To a stirred boiling solution of 0.1 mol (11.4 g) of 1,2-diaminocyclohexane in 60 ml p-xylene, 0.12 mol (23.06 g) of ethyl benzoylacetate in 10 ml p-xylene was added dropwise and refluxed for 2 h. The reaction mixture was left at room temperature for 24 h. The precipitated solid was collected by filtration and recrystallized from dry ethanol solution to give colourless blocks (m.p. 230–232°C).
Refinement
Crystal and . The cyclohexyl ring and its attached N atoms are disordered over two chair conformations in a 91:9 ratio. The minor component of the disorder was restrained to have a comparable geometry to that of the major one and the attached H atoms on both were included as riding contributions in idealized positions. The final model was refined as a two-component twin.
details are presented in Table 2Structural data
CCDC reference: 1855622
https://doi.org/10.1107/S2414314618010118/hb4246sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314618010118/hb4246Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314618010118/hb4246Isup3.cml
Data 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: SHELXL (Sheldrick, 2015b); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXTL (Bruker, 2016).C15H18N2O | F(000) = 520 |
Mr = 242.31 | Dx = 1.243 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 11.4283 (18) Å | Cell parameters from 9967 reflections |
b = 9.2294 (15) Å | θ = 2.8–29.2° |
c = 12.3632 (19) Å | µ = 0.08 mm−1 |
β = 96.890 (2)° | T = 100 K |
V = 1294.6 (4) Å3 | Block, colourless |
Z = 4 | 0.30 × 0.27 × 0.19 mm |
Bruker SMART APEX CCD diffractometer | 44744 independent reflections |
Radiation source: fine-focus sealed tube | 25002 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.046 |
Detector resolution: 8.3333 pixels mm-1 | θmax = 29.2°, θmin = 1.8° |
ω and φ scans | h = −15→15 |
Absorption correction: multi-scan (TWINABS; Sheldrick, 2009) | k = −12→12 |
Tmin = 0.98, Tmax = 0.99 | l = −16→16 |
44744 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.054 | Hydrogen site location: mixed |
wR(F2) = 0.152 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.93 | w = 1/[σ2(Fo2) + (0.0804P)2] where P = (Fo2 + 2Fc2)/3 |
44744 reflections | (Δ/σ)max < 0.001 |
207 parameters | Δρmax = 0.32 e Å−3 |
18 restraints | Δρmin = −0.24 e Å−3 |
Experimental. The diffraction data were obtained from 3 sets of 400 frames, each of width 0.5 deg. in omega, colllected at phi = 0.00, 90.00 and 180.00 deg. and 2 sets of 800 frames, each of width 0.45 deg in phi, collected at omega = -30.00 and 210.00 deg. The scan time was 30 sec/frame. Analysis of 1323 reflections having I/σ(I) > 12 and chosen from the full data set with CELL_NOW (Sheldrick, 2008) showed the crystal to belong to the monoclinic system and to be twinned by a 180° rotation about b. The raw data were processed using the multi-component version of SAINT under control of the two-component orientation file generated by CELL_NOW. |
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. The cyclohexyl ring and its attached nitrogen atoms are disordered over two chair conformations in a 91:9 ratio. The minor component of the disorder was restrained to have a comparable geometry to that of the major one and the attached hydrogens on both were included as riding contributions in idealized positions. The final model was refined as a 2-component twin. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O1 | 0.35039 (10) | 0.54728 (14) | 0.97683 (10) | 0.0323 (4) | |
N1 | 0.35229 (12) | 0.69692 (17) | 0.63902 (12) | 0.0309 (4) | 0.911 (2) |
H1B | 0.336391 | 0.742292 | 0.576378 | 0.037* | 0.911 (2) |
N2 | 0.48216 (12) | 0.58638 (16) | 0.85897 (12) | 0.0291 (4) | 0.911 (2) |
H2 | 0.530411 | 0.528523 | 0.899541 | 0.035* | 0.911 (2) |
C1 | 0.53237 (16) | 0.6625 (2) | 0.77215 (16) | 0.0264 (5) | 0.911 (2) |
H1 | 0.527560 | 0.769274 | 0.784632 | 0.032* | 0.911 (2) |
C2 | 0.66216 (17) | 0.6171 (3) | 0.78221 (19) | 0.0338 (7) | 0.911 (2) |
H2A | 0.702263 | 0.651335 | 0.853023 | 0.041* | 0.911 (2) |
H2B | 0.666875 | 0.510004 | 0.781610 | 0.041* | 0.911 (2) |
C3 | 0.72628 (18) | 0.6767 (3) | 0.69142 (18) | 0.0359 (6) | 0.911 (2) |
H3A | 0.809178 | 0.643256 | 0.701073 | 0.043* | 0.911 (2) |
H3B | 0.726174 | 0.783939 | 0.693833 | 0.043* | 0.911 (2) |
C4 | 0.66544 (18) | 0.6250 (3) | 0.58212 (19) | 0.0367 (6) | 0.911 (2) |
H4A | 0.668078 | 0.517946 | 0.578709 | 0.044* | 0.911 (2) |
H4B | 0.706872 | 0.664164 | 0.522574 | 0.044* | 0.911 (2) |
C5 | 0.53792 (17) | 0.6761 (2) | 0.56791 (17) | 0.0303 (6) | 0.911 (2) |
H5A | 0.498609 | 0.639623 | 0.497463 | 0.036* | 0.911 (2) |
H5B | 0.536658 | 0.783314 | 0.564929 | 0.036* | 0.911 (2) |
C6 | 0.46797 (16) | 0.6259 (2) | 0.65916 (16) | 0.0259 (5) | 0.911 (2) |
H6 | 0.456677 | 0.518621 | 0.653614 | 0.031* | 0.911 (2) |
N1A | 0.35229 (12) | 0.69692 (17) | 0.63902 (12) | 0.0309 (4) | 0.089 (2) |
H1C | 0.331921 | 0.683920 | 0.568769 | 0.037* | 0.089 (2) |
N2A | 0.48216 (12) | 0.58638 (16) | 0.85897 (12) | 0.0291 (4) | 0.089 (2) |
H2C | 0.538385 | 0.583969 | 0.914203 | 0.035* | 0.089 (2) |
C1A | 0.5210 (11) | 0.5822 (19) | 0.7504 (9) | 0.0264 (5) | 0.089 (2) |
H1A | 0.489134 | 0.492652 | 0.712003 | 0.032* | 0.089 (2) |
C2A | 0.6553 (12) | 0.573 (3) | 0.7681 (15) | 0.0338 (7) | 0.089 (2) |
H2AA | 0.685897 | 0.652867 | 0.816838 | 0.041* | 0.089 (2) |
H2AB | 0.678265 | 0.480545 | 0.805409 | 0.041* | 0.089 (2) |
C3A | 0.7129 (15) | 0.581 (2) | 0.6642 (16) | 0.0359 (6) | 0.089 (2) |
H3AA | 0.688596 | 0.496789 | 0.617389 | 0.043* | 0.089 (2) |
H3AB | 0.799659 | 0.578199 | 0.681997 | 0.043* | 0.089 (2) |
C4A | 0.6773 (13) | 0.720 (2) | 0.6032 (18) | 0.0367 (6) | 0.089 (2) |
H4AA | 0.712770 | 0.723251 | 0.533981 | 0.044* | 0.089 (2) |
H4AB | 0.706448 | 0.804972 | 0.647678 | 0.044* | 0.089 (2) |
C5A | 0.5437 (12) | 0.727 (3) | 0.5796 (14) | 0.0303 (6) | 0.089 (2) |
H5AA | 0.516753 | 0.646747 | 0.529269 | 0.036* | 0.089 (2) |
H5AB | 0.521217 | 0.819029 | 0.542015 | 0.036* | 0.089 (2) |
C6A | 0.4795 (8) | 0.7153 (18) | 0.6810 (11) | 0.0259 (5) | 0.089 (2) |
H6A | 0.491302 | 0.805811 | 0.725432 | 0.031* | 0.089 (2) |
C7 | 0.26759 (14) | 0.69980 (19) | 0.70681 (15) | 0.0251 (4) | |
C8 | 0.27531 (16) | 0.65248 (19) | 0.81167 (15) | 0.0264 (4) | |
C9 | 0.37109 (15) | 0.59344 (19) | 0.88495 (15) | 0.0255 (4) | |
C10 | 0.15212 (15) | 0.7588 (2) | 0.65637 (16) | 0.0284 (4) | |
H10 | 0.1482 (17) | 0.650 (2) | 0.5102 (16) | 0.039 (6)* | |
C11 | 0.10522 (17) | 0.7196 (2) | 0.55146 (18) | 0.0376 (5) | |
H11 | −0.0345 (19) | 0.738 (2) | 0.4304 (18) | 0.052 (6)* | |
C12 | −0.00385 (18) | 0.7731 (3) | 0.5068 (2) | 0.0456 (6) | |
H12 | −0.1426 (19) | 0.906 (2) | 0.5324 (17) | 0.047 (6)* | |
C13 | −0.06599 (18) | 0.8668 (3) | 0.5657 (2) | 0.0447 (6) | |
H13 | −0.0647 (19) | 0.971 (2) | 0.7134 (17) | 0.048 (6)* | |
C14 | −0.02046 (18) | 0.9060 (2) | 0.6693 (2) | 0.0426 (6) | |
H14 | 0.2059 (16) | 0.6540 (19) | 0.8426 (14) | 0.028 (5)* | |
C15 | 0.08779 (16) | 0.8525 (2) | 0.71489 (18) | 0.0346 (5) | |
H15 | 0.1212 (17) | 0.881 (2) | 0.7891 (17) | 0.038 (6)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0263 (7) | 0.0473 (9) | 0.0239 (8) | 0.0017 (6) | 0.0055 (5) | 0.0068 (6) |
N1 | 0.0225 (8) | 0.0477 (10) | 0.0230 (9) | 0.0055 (7) | 0.0040 (7) | 0.0068 (7) |
N2 | 0.0214 (8) | 0.0412 (10) | 0.0253 (9) | 0.0048 (6) | 0.0052 (6) | 0.0079 (7) |
C1 | 0.0227 (10) | 0.0308 (12) | 0.0265 (12) | −0.0013 (8) | 0.0063 (8) | 0.0017 (9) |
C2 | 0.0228 (10) | 0.0436 (17) | 0.0351 (13) | 0.0008 (9) | 0.0038 (9) | 0.0074 (11) |
C3 | 0.0234 (10) | 0.0419 (15) | 0.0433 (15) | 0.0004 (9) | 0.0080 (10) | 0.0096 (11) |
C4 | 0.0312 (11) | 0.0425 (14) | 0.0391 (14) | 0.0049 (10) | 0.0156 (10) | 0.0048 (11) |
C5 | 0.0284 (10) | 0.0371 (15) | 0.0265 (12) | 0.0026 (9) | 0.0087 (8) | 0.0015 (10) |
C6 | 0.0222 (10) | 0.0296 (12) | 0.0264 (12) | 0.0024 (8) | 0.0049 (8) | 0.0009 (9) |
N1A | 0.0225 (8) | 0.0477 (10) | 0.0230 (9) | 0.0055 (7) | 0.0040 (7) | 0.0068 (7) |
N2A | 0.0214 (8) | 0.0412 (10) | 0.0253 (9) | 0.0048 (6) | 0.0052 (6) | 0.0079 (7) |
C1A | 0.0227 (10) | 0.0308 (12) | 0.0265 (12) | −0.0013 (8) | 0.0063 (8) | 0.0017 (9) |
C2A | 0.0228 (10) | 0.0436 (17) | 0.0351 (13) | 0.0008 (9) | 0.0038 (9) | 0.0074 (11) |
C3A | 0.0234 (10) | 0.0419 (15) | 0.0433 (15) | 0.0004 (9) | 0.0080 (10) | 0.0096 (11) |
C4A | 0.0312 (11) | 0.0425 (14) | 0.0391 (14) | 0.0049 (10) | 0.0156 (10) | 0.0048 (11) |
C5A | 0.0284 (10) | 0.0371 (15) | 0.0265 (12) | 0.0026 (9) | 0.0087 (8) | 0.0015 (10) |
C6A | 0.0222 (10) | 0.0296 (12) | 0.0264 (12) | 0.0024 (8) | 0.0049 (8) | 0.0009 (9) |
C7 | 0.0200 (8) | 0.0286 (10) | 0.0269 (11) | −0.0008 (7) | 0.0036 (7) | 0.0002 (8) |
C8 | 0.0195 (9) | 0.0338 (11) | 0.0269 (11) | 0.0004 (7) | 0.0062 (8) | 0.0020 (8) |
C9 | 0.0224 (9) | 0.0303 (10) | 0.0241 (10) | −0.0008 (7) | 0.0048 (7) | −0.0018 (8) |
C10 | 0.0206 (9) | 0.0361 (11) | 0.0287 (11) | −0.0005 (7) | 0.0041 (8) | 0.0078 (8) |
C11 | 0.0279 (10) | 0.0523 (14) | 0.0326 (13) | 0.0006 (9) | 0.0032 (9) | 0.0050 (10) |
C12 | 0.0295 (11) | 0.0690 (16) | 0.0362 (14) | −0.0041 (10) | −0.0042 (10) | 0.0123 (11) |
C13 | 0.0202 (10) | 0.0603 (15) | 0.0533 (16) | 0.0024 (9) | 0.0036 (10) | 0.0244 (12) |
C14 | 0.0281 (11) | 0.0490 (14) | 0.0525 (16) | 0.0097 (9) | 0.0117 (10) | 0.0143 (11) |
C15 | 0.0261 (10) | 0.0423 (12) | 0.0359 (13) | 0.0037 (8) | 0.0054 (9) | 0.0068 (9) |
O1—C9 | 1.262 (2) | C1A—C6A | 1.541 (10) |
N1—C7 | 1.354 (2) | C1A—H1A | 1.0000 |
N1—C6 | 1.470 (2) | C2A—C3A | 1.514 (10) |
N1—H1B | 0.8800 | C2A—H2AA | 0.9900 |
N2—C9 | 1.348 (2) | C2A—H2AB | 0.9900 |
N2—C1 | 1.457 (2) | C3A—C4A | 1.519 (10) |
N2—H2 | 0.8800 | C3A—H3AA | 0.9900 |
C1—C2 | 1.532 (3) | C3A—H3AB | 0.9900 |
C1—C6 | 1.536 (3) | C4A—C5A | 1.521 (10) |
C1—H1 | 1.0000 | C4A—H4AA | 0.9900 |
C2—C3 | 1.515 (3) | C4A—H4AB | 0.9900 |
C2—H2A | 0.9900 | C5A—C6A | 1.529 (10) |
C2—H2B | 0.9900 | C5A—H5AA | 0.9900 |
C3—C4 | 1.520 (3) | C5A—H5AB | 0.9900 |
C3—H3A | 0.9900 | C6A—H6A | 1.0000 |
C3—H3B | 0.9900 | C7—C8 | 1.361 (2) |
C4—C5 | 1.522 (3) | C7—C10 | 1.493 (2) |
C4—H4A | 0.9900 | C8—C9 | 1.441 (2) |
C4—H4B | 0.9900 | C8—H14 | 0.922 (18) |
C5—C6 | 1.531 (3) | C10—C11 | 1.391 (3) |
C5—H5A | 0.9900 | C10—C15 | 1.392 (3) |
C5—H5B | 0.9900 | C11—C12 | 1.392 (3) |
C6—H6 | 1.0000 | C11—H10 | 0.99 (2) |
N1A—C7 | 1.354 (2) | C12—C13 | 1.381 (3) |
N1A—C6A | 1.494 (9) | C12—H11 | 1.02 (2) |
N1A—H1C | 0.8800 | C13—C14 | 1.372 (3) |
N2A—C9 | 1.348 (2) | C13—H12 | 0.99 (2) |
N2A—C1A | 1.464 (9) | C14—C15 | 1.388 (3) |
N2A—H2C | 0.8800 | C14—H13 | 0.99 (2) |
C1A—C2A | 1.526 (10) | C15—H15 | 0.99 (2) |
C7—N1—C6 | 126.79 (15) | C1A—C2A—H2AB | 108.7 |
C7—N1—H1B | 116.6 | H2AA—C2A—H2AB | 107.6 |
C6—N1—H1B | 116.6 | C2A—C3A—C4A | 110.2 (12) |
C9—N2—C1 | 128.15 (15) | C2A—C3A—H3AA | 109.6 |
C9—N2—H2 | 115.9 | C4A—C3A—H3AA | 109.6 |
C1—N2—H2 | 115.9 | C2A—C3A—H3AB | 109.6 |
N2—C1—C2 | 105.75 (16) | C4A—C3A—H3AB | 109.6 |
N2—C1—C6 | 112.07 (16) | H3AA—C3A—H3AB | 108.1 |
C2—C1—C6 | 111.55 (16) | C3A—C4A—C5A | 109.3 (12) |
N2—C1—H1 | 109.1 | C3A—C4A—H4AA | 109.8 |
C2—C1—H1 | 109.1 | C5A—C4A—H4AA | 109.8 |
C6—C1—H1 | 109.1 | C3A—C4A—H4AB | 109.8 |
C3—C2—C1 | 112.96 (18) | C5A—C4A—H4AB | 109.8 |
C3—C2—H2A | 109.0 | H4AA—C4A—H4AB | 108.3 |
C1—C2—H2A | 109.0 | C4A—C5A—C6A | 114.2 (11) |
C3—C2—H2B | 109.0 | C4A—C5A—H5AA | 108.7 |
C1—C2—H2B | 109.0 | C6A—C5A—H5AA | 108.7 |
H2A—C2—H2B | 107.8 | C4A—C5A—H5AB | 108.7 |
C2—C3—C4 | 109.52 (18) | C6A—C5A—H5AB | 108.7 |
C2—C3—H3A | 109.8 | H5AA—C5A—H5AB | 107.6 |
C4—C3—H3A | 109.8 | N1A—C6A—C5A | 105.4 (9) |
C2—C3—H3B | 109.8 | N1A—C6A—C1A | 108.9 (10) |
C4—C3—H3B | 109.8 | C5A—C6A—C1A | 111.4 (11) |
H3A—C3—H3B | 108.2 | N1A—C6A—H6A | 110.3 |
C3—C4—C5 | 109.57 (18) | C5A—C6A—H6A | 110.3 |
C3—C4—H4A | 109.8 | C1A—C6A—H6A | 110.3 |
C5—C4—H4A | 109.8 | N1A—C7—C8 | 127.86 (16) |
C3—C4—H4B | 109.8 | N1—C7—C8 | 127.86 (16) |
C5—C4—H4B | 109.8 | N1A—C7—C10 | 114.21 (15) |
H4A—C4—H4B | 108.2 | N1—C7—C10 | 114.21 (15) |
C4—C5—C6 | 113.50 (18) | C8—C7—C10 | 117.90 (15) |
C4—C5—H5A | 108.9 | C7—C8—C9 | 132.66 (17) |
C6—C5—H5A | 108.9 | C7—C8—H14 | 115.5 (11) |
C4—C5—H5B | 108.9 | C9—C8—H14 | 111.8 (11) |
C6—C5—H5B | 108.9 | O1—C9—N2A | 118.81 (16) |
H5A—C5—H5B | 107.7 | O1—C9—N2 | 118.81 (16) |
N1—C6—C5 | 106.19 (15) | O1—C9—C8 | 118.89 (16) |
N1—C6—C1 | 112.28 (15) | N2A—C9—C8 | 122.30 (16) |
C5—C6—C1 | 111.59 (16) | N2—C9—C8 | 122.30 (16) |
N1—C6—H6 | 108.9 | C11—C10—C15 | 118.54 (18) |
C5—C6—H6 | 108.9 | C11—C10—C7 | 121.13 (17) |
C1—C6—H6 | 108.9 | C15—C10—C7 | 120.31 (18) |
C7—N1A—C6A | 121.4 (6) | C10—C11—C12 | 120.3 (2) |
C7—N1A—H1C | 119.3 | C10—C11—H10 | 119.4 (11) |
C6A—N1A—H1C | 119.3 | C12—C11—H10 | 120.2 (11) |
C9—N2A—C1A | 128.1 (5) | C13—C12—C11 | 120.4 (2) |
C9—N2A—H2C | 115.9 | C13—C12—H11 | 123.1 (12) |
C1A—N2A—H2C | 115.9 | C11—C12—H11 | 116.5 (12) |
N2A—C1A—C2A | 106.3 (9) | C14—C13—C12 | 119.7 (2) |
N2A—C1A—C6A | 112.5 (10) | C14—C13—H12 | 120.5 (12) |
C2A—C1A—C6A | 111.2 (11) | C12—C13—H12 | 119.8 (12) |
N2A—C1A—H1A | 108.9 | C13—C14—C15 | 120.4 (2) |
C2A—C1A—H1A | 108.9 | C13—C14—H13 | 120.9 (12) |
C6A—C1A—H1A | 108.9 | C15—C14—H13 | 118.7 (13) |
C3A—C2A—C1A | 114.1 (12) | C14—C15—C10 | 120.7 (2) |
C3A—C2A—H2AA | 108.7 | C14—C15—H15 | 120.5 (11) |
C1A—C2A—H2AA | 108.7 | C10—C15—H15 | 118.8 (11) |
C3A—C2A—H2AB | 108.7 | ||
C9—N2—C1—C2 | 178.49 (18) | C2A—C1A—C6A—C5A | 47.7 (17) |
C9—N2—C1—C6 | −59.8 (3) | C6A—N1A—C7—C8 | −33.3 (8) |
N2—C1—C2—C3 | 175.09 (18) | C6A—N1A—C7—C10 | 148.6 (7) |
C6—C1—C2—C3 | 53.0 (3) | C6—N1—C7—C8 | 7.9 (3) |
C1—C2—C3—C4 | −58.6 (3) | C6—N1—C7—C10 | −170.20 (17) |
C2—C3—C4—C5 | 59.2 (2) | N1A—C7—C8—C9 | 3.5 (3) |
C3—C4—C5—C6 | −57.0 (2) | N1—C7—C8—C9 | 3.5 (3) |
C7—N1—C6—C5 | −170.40 (17) | C10—C7—C8—C9 | −178.47 (19) |
C7—N1—C6—C1 | −48.2 (2) | C1A—N2A—C9—O1 | 155.9 (9) |
C4—C5—C6—N1 | 174.11 (17) | C1A—N2A—C9—C8 | −24.4 (9) |
C4—C5—C6—C1 | 51.5 (2) | C1—N2—C9—O1 | −163.67 (18) |
N2—C1—C6—N1 | 74.5 (2) | C1—N2—C9—C8 | 16.0 (3) |
C2—C1—C6—N1 | −167.09 (16) | C7—C8—C9—O1 | −174.44 (19) |
N2—C1—C6—C5 | −166.35 (16) | C7—C8—C9—N2A | 5.9 (3) |
C2—C1—C6—C5 | −48.0 (2) | C7—C8—C9—N2 | 5.9 (3) |
C9—N2A—C1A—C2A | −179.4 (11) | N1A—C7—C10—C11 | 43.1 (2) |
C9—N2A—C1A—C6A | 58.6 (15) | N1—C7—C10—C11 | 43.1 (2) |
N2A—C1A—C2A—C3A | −174.7 (17) | C8—C7—C10—C11 | −135.20 (19) |
C6A—C1A—C2A—C3A | −52 (2) | N1A—C7—C10—C15 | −138.29 (18) |
C1A—C2A—C3A—C4A | 57 (2) | N1—C7—C10—C15 | −138.29 (18) |
C2A—C3A—C4A—C5A | −57 (2) | C8—C7—C10—C15 | 43.4 (2) |
C3A—C4A—C5A—C6A | 57 (2) | C15—C10—C11—C12 | −0.2 (3) |
C7—N1A—C6A—C5A | −172.4 (10) | C7—C10—C11—C12 | 178.49 (18) |
C7—N1A—C6A—C1A | 67.9 (12) | C10—C11—C12—C13 | 0.7 (3) |
C4A—C5A—C6A—N1A | −170.1 (15) | C11—C12—C13—C14 | −0.7 (3) |
C4A—C5A—C6A—C1A | −52 (2) | C12—C13—C14—C15 | 0.3 (3) |
N2A—C1A—C6A—N1A | −77.3 (15) | C13—C14—C15—C10 | 0.3 (3) |
C2A—C1A—C6A—N1A | 163.6 (13) | C11—C10—C15—C14 | −0.3 (3) |
N2A—C1A—C6A—C5A | 166.9 (13) | C7—C10—C15—C14 | −178.97 (18) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1B···O1i | 0.88 | 2.32 | 3.096 (2) | 148 |
N2—H2···O1ii | 0.88 | 2.04 | 2.8936 (19) | 162 |
Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) −x+1, −y+1, −z+2. |
Acknowledgements
JTM thanks Tulane University for support of the Tulane Crystallography Laboratory.
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