organic compounds
2-(2-Oxo-4-phenyl-2,3-dihydro-1H-1,5-benzodiazepin-1-yl)acetic acid
aLaboratoire de Chimie Organique Hétérocyclique, URAC 21, Pôle de Compétence Pharmacochimie, Av Ibn Battouta, BP 1014, Faculté des Sciences, Université Mohammed V, Rabat, Morocco, and bDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA
*Correspondence e-mail: essaghouani.hanine@gmail.com
The 17H14N2O3, consists of two independent molecules having distinctly different conformations. The components of the are connected by an O—H⋯N hydrogen bond, with additional O—H⋯N hydrogen bonds connecting this assemblage into chains running parallel to the b axis. Intermolecular C—H⋯π(ring) interactions are also present.
of the title compound, CCCDC reference: 1529295
Structure description
As a continuation of our studies on substituted 1,5-benzodiazepin-2-one derivatives (Essaghouani et al., 2016; Ballo et al., 2010), we report the synthesis of a new 1,5-benzodiazepin-2-one derivative by the hydrolysis reaction with an aqueous solution of potassium hydroxide of ethyl 2-(2-oxo-4-phenyl-2,3-dihydro-1H-1,5-benzodiazepin-1-yl)acetate in ethanol.
The ) consists of two independent molecules which differ markedly in their conformations. This can be seen, in part, from the puckering parameters for the seven-membered rings. For the ring N1,C1,C6,N2,C7,C8,C9, Q(2) = 0.881 (1) Å, Q(3) = 0.218 (1) Å, φ(2) = 203.79 (7)° and φ(3) = 307.7 (3)° with a total puckering amplitude of 0.907 (1) Å, while for the ring N3,C18,C23,N4,C24,C25,C26, the corresponding values are 0.904 (1) Å, 0.234 (1) Å, 25.64 (7)° and 125.9 (3)° with a total puckering amplitude of 0.934 (1) Å. Additionally, the dihedral angle between the C1–C6 and C12–C17 rings is 72.18 (4)° while that between the C18–C22 and C29–C34 rings is 80.03 (4)°.
(Fig. 1In the crystal, the molecules are linked into chains running parallel to the b axis by O2—H2A⋯N4 and O6—H6⋯N2iii [symmetry code: (iii) x, y + 1, z] hydrogen bonds (Table 1 and Fig. 2). Finally there are two sets of C—H⋯π(ring) interactions (Fig. 3).
Synthesis and crystallization
A solution of potassium hydroxide (12.0 mmol) in water (5 ml) was added to the solution of ethyl 2-(2-oxo-4-phenyl-2,3-dihydro-1H-1,5-benzodiazepin-1-yl)acetate (3.0 mmol) in ethanol (10 ml). The resulting reaction mixture was stirred at room temperature for 6 h, after completion of the reaction (monitored by TLC). The reaction mixture was poured into water and acidified with 3M HCl to form the title compound as a yellow solid. The solid product was purified by recrystallization from ethanol solution to afford the title compound as yellow crystals (yield 84%).
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2
|
Structural data
CCDC reference: 1529295
https://doi.org/10.1107/S2414314617001201/bv4007sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617001201/bv4007Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314617001201/bv4007Isup3.cdx
Supporting information file. DOI: https://doi.org/10.1107/S2414314617001201/bv4007Isup4.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: SHELXL2014 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).C17H14N2O3 | F(000) = 1232 |
Mr = 294.30 | Dx = 1.384 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 17.9752 (8) Å | Cell parameters from 9857 reflections |
b = 17.4403 (8) Å | θ = 2.3–28.8° |
c = 9.2472 (4) Å | µ = 0.10 mm−1 |
β = 102.892 (1)° | T = 298 K |
V = 2825.9 (2) Å3 | Block, yellow |
Z = 8 | 0.32 × 0.29 × 0.28 mm |
Bruker SMART APEX CCD diffractometer | 7627 independent reflections |
Radiation source: fine-focus sealed tube | 5791 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.033 |
Detector resolution: 8.3333 pixels mm-1 | θmax = 29.2°, θmin = 1.7° |
φ and ω scans | h = −24→24 |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | k = −23→23 |
Tmin = 0.89, Tmax = 0.97 | l = −12→12 |
54166 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)] = 0.048 | Hydrogen site location: mixed |
wR(F2) = 0.146 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.11 | w = 1/[σ2(Fo2) + (0.0941P)2 + 0.0156P] where P = (Fo2 + 2Fc2)/3 |
7627 reflections | (Δ/σ)max = 0.001 |
503 parameters | Δρmax = 0.36 e Å−3 |
0 restraints | Δρmin = −0.21 e Å−3 |
Experimental. The diffraction data were obtained from 3 sets of 400 frames, each of width 0.5° in ω, collected at φ = 0.00, 90.00 and 180.00° and 2 sets of 800 frames, each of width 0.45° in φ, collected at ω = –30.00 and 210.00°. The scan time was 15 sec/frame. |
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. Hydrogens attached to oxygen were placed in calculated positions and included as riding contributions. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.60331 (5) | 0.13791 (5) | 0.27570 (13) | 0.0536 (3) | |
O2 | 0.70218 (5) | 0.30973 (5) | 0.14443 (10) | 0.0448 (2) | |
H2A | 0.7194 | 0.3483 | 0.1907 | 0.067* | |
O3 | 0.76238 (7) | 0.24959 (5) | 0.34987 (10) | 0.0523 (3) | |
N1 | 0.71781 (5) | 0.10783 (5) | 0.22680 (11) | 0.0335 (2) | |
N2 | 0.72769 (5) | −0.06012 (5) | 0.28503 (11) | 0.0338 (2) | |
C1 | 0.78810 (6) | 0.06741 (6) | 0.26215 (12) | 0.0325 (2) | |
C2 | 0.85619 (7) | 0.10630 (7) | 0.26274 (15) | 0.0429 (3) | |
H2 | 0.8576 (8) | 0.1607 (10) | 0.2436 (17) | 0.054 (4)* | |
C3 | 0.92572 (8) | 0.06889 (9) | 0.29592 (17) | 0.0498 (3) | |
H3 | 0.9738 (9) | 0.0964 (10) | 0.3011 (19) | 0.061 (4)* | |
C4 | 0.92926 (7) | −0.00864 (9) | 0.32758 (16) | 0.0488 (3) | |
H4 | 0.9792 (9) | −0.0350 (9) | 0.3519 (17) | 0.054 (4)* | |
C5 | 0.86265 (7) | −0.04874 (8) | 0.32415 (15) | 0.0428 (3) | |
H5 | 0.8635 (8) | −0.1047 (9) | 0.3472 (16) | 0.049 (4)* | |
C6 | 0.79178 (6) | −0.01189 (6) | 0.29224 (13) | 0.0337 (2) | |
C7 | 0.67194 (6) | −0.03881 (6) | 0.34201 (12) | 0.0306 (2) | |
C8 | 0.67410 (7) | 0.03717 (6) | 0.41964 (13) | 0.0351 (2) | |
H8A | 0.6343 (7) | 0.0428 (7) | 0.4751 (15) | 0.038 (3)* | |
H8B | 0.7249 (8) | 0.0453 (8) | 0.4914 (15) | 0.043 (4)* | |
C9 | 0.66091 (6) | 0.09902 (6) | 0.30295 (13) | 0.0349 (2) | |
C10 | 0.70987 (8) | 0.17555 (6) | 0.13187 (14) | 0.0371 (3) | |
H10A | 0.7430 (8) | 0.1719 (8) | 0.0700 (16) | 0.042 (4)* | |
H10B | 0.6579 (9) | 0.1776 (9) | 0.0709 (17) | 0.053 (4)* | |
C11 | 0.72781 (7) | 0.24848 (6) | 0.22292 (13) | 0.0351 (2) | |
C12 | 0.60495 (6) | −0.08991 (6) | 0.33007 (13) | 0.0336 (2) | |
C13 | 0.58545 (8) | −0.14086 (8) | 0.21200 (16) | 0.0478 (3) | |
H13 | 0.6142 (9) | −0.1415 (9) | 0.1355 (18) | 0.058 (4)* | |
C14 | 0.52507 (9) | −0.19148 (9) | 0.2063 (2) | 0.0638 (4) | |
H14 | 0.5166 (13) | −0.2278 (14) | 0.127 (3) | 0.103 (7)* | |
C15 | 0.48451 (9) | −0.19212 (9) | 0.3147 (2) | 0.0627 (4) | |
H15 | 0.4416 (10) | −0.2285 (10) | 0.3082 (19) | 0.068 (5)* | |
C16 | 0.50222 (8) | −0.14105 (8) | 0.43070 (19) | 0.0527 (4) | |
H16 | 0.4772 (11) | −0.1397 (11) | 0.505 (2) | 0.075 (5)* | |
C17 | 0.56172 (7) | −0.08953 (7) | 0.43804 (15) | 0.0410 (3) | |
H17 | 0.5723 (8) | −0.0524 (10) | 0.5231 (18) | 0.056 (4)* | |
O4 | 0.90968 (5) | 0.61482 (6) | 0.27642 (12) | 0.0522 (3) | |
O5 | 0.81149 (7) | 0.75579 (5) | 0.35900 (11) | 0.0582 (3) | |
O6 | 0.74537 (7) | 0.80350 (5) | 0.14535 (11) | 0.0572 (3) | |
H6 | 0.7438 | 0.8422 | 0.1948 | 0.086* | |
N3 | 0.78152 (5) | 0.60652 (5) | 0.25031 (11) | 0.0330 (2) | |
N4 | 0.76233 (5) | 0.43981 (5) | 0.28495 (10) | 0.0323 (2) | |
C18 | 0.71694 (6) | 0.57473 (6) | 0.29305 (12) | 0.0308 (2) | |
C19 | 0.65708 (7) | 0.62319 (7) | 0.30917 (14) | 0.0408 (3) | |
H19 | 0.6625 (8) | 0.6793 (9) | 0.3044 (16) | 0.050 (4)* | |
C20 | 0.59079 (7) | 0.59410 (8) | 0.33805 (16) | 0.0477 (3) | |
H20 | 0.5497 (10) | 0.6274 (10) | 0.3508 (18) | 0.064 (5)* | |
C21 | 0.58232 (7) | 0.51563 (9) | 0.35311 (16) | 0.0492 (3) | |
H21 | 0.5326 (8) | 0.4907 (9) | 0.3709 (16) | 0.047 (4)* | |
C22 | 0.64072 (7) | 0.46703 (7) | 0.33788 (14) | 0.0417 (3) | |
H22 | 0.6367 (7) | 0.4087 (8) | 0.3431 (15) | 0.044 (4)* | |
C23 | 0.70850 (6) | 0.49519 (6) | 0.30834 (12) | 0.0319 (2) | |
C24 | 0.83437 (6) | 0.45013 (6) | 0.33622 (12) | 0.0320 (2) | |
C25 | 0.86337 (7) | 0.52106 (6) | 0.42453 (13) | 0.0361 (2) | |
H25A | 0.9180 (8) | 0.5147 (8) | 0.4696 (16) | 0.044 (4)* | |
H25B | 0.8342 (8) | 0.5321 (8) | 0.4972 (16) | 0.043 (4)* | |
C26 | 0.85536 (6) | 0.58557 (6) | 0.31257 (14) | 0.0352 (2) | |
C27 | 0.77099 (8) | 0.67215 (6) | 0.15010 (14) | 0.0374 (3) | |
H27A | 0.8080 (8) | 0.6687 (8) | 0.0928 (16) | 0.045 (4)* | |
H27B | 0.7230 (8) | 0.6712 (8) | 0.0886 (15) | 0.040 (4)* | |
C28 | 0.77890 (7) | 0.74808 (6) | 0.23226 (14) | 0.0370 (3) | |
C29 | 0.88927 (6) | 0.39373 (6) | 0.30039 (13) | 0.0343 (2) | |
C30 | 0.95522 (7) | 0.37419 (7) | 0.40601 (14) | 0.0399 (3) | |
H30 | 0.9649 (8) | 0.3990 (9) | 0.5045 (18) | 0.053 (4)* | |
C31 | 1.00541 (8) | 0.32027 (8) | 0.37314 (17) | 0.0473 (3) | |
H31 | 1.0518 (9) | 0.3082 (9) | 0.4463 (16) | 0.049 (4)* | |
C32 | 0.99114 (8) | 0.28555 (8) | 0.23510 (18) | 0.0522 (3) | |
H32 | 1.0269 (10) | 0.2474 (10) | 0.214 (2) | 0.070 (5)* | |
C33 | 0.92654 (8) | 0.30505 (8) | 0.12984 (17) | 0.0506 (3) | |
H33 | 0.9169 (9) | 0.2840 (11) | 0.035 (2) | 0.062 (5)* | |
C34 | 0.87589 (7) | 0.35883 (7) | 0.16167 (14) | 0.0422 (3) | |
H34 | 0.8301 (9) | 0.3742 (9) | 0.0780 (17) | 0.058 (4)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0432 (5) | 0.0407 (5) | 0.0819 (7) | 0.0120 (4) | 0.0244 (5) | 0.0092 (5) |
O2 | 0.0514 (5) | 0.0230 (4) | 0.0563 (5) | 0.0006 (3) | 0.0041 (4) | −0.0014 (3) |
O3 | 0.0790 (7) | 0.0336 (5) | 0.0432 (5) | −0.0009 (4) | 0.0113 (5) | −0.0035 (4) |
N1 | 0.0369 (5) | 0.0214 (4) | 0.0453 (5) | 0.0001 (3) | 0.0157 (4) | 0.0017 (4) |
N2 | 0.0356 (5) | 0.0217 (4) | 0.0458 (5) | −0.0001 (3) | 0.0127 (4) | 0.0007 (4) |
C1 | 0.0348 (5) | 0.0251 (5) | 0.0405 (6) | −0.0018 (4) | 0.0146 (4) | −0.0031 (4) |
C2 | 0.0420 (7) | 0.0348 (6) | 0.0577 (8) | −0.0076 (5) | 0.0239 (6) | −0.0039 (5) |
C3 | 0.0373 (7) | 0.0547 (8) | 0.0625 (8) | −0.0112 (6) | 0.0218 (6) | −0.0108 (6) |
C4 | 0.0327 (6) | 0.0549 (8) | 0.0603 (8) | 0.0057 (6) | 0.0140 (6) | −0.0049 (6) |
C5 | 0.0394 (6) | 0.0369 (6) | 0.0542 (7) | 0.0066 (5) | 0.0150 (5) | 0.0007 (5) |
C6 | 0.0340 (5) | 0.0267 (5) | 0.0428 (6) | −0.0004 (4) | 0.0138 (5) | −0.0024 (4) |
C7 | 0.0351 (5) | 0.0225 (5) | 0.0346 (5) | −0.0007 (4) | 0.0087 (4) | 0.0028 (4) |
C8 | 0.0398 (6) | 0.0282 (5) | 0.0409 (6) | −0.0046 (4) | 0.0167 (5) | −0.0039 (4) |
C9 | 0.0344 (6) | 0.0230 (5) | 0.0497 (6) | −0.0012 (4) | 0.0142 (5) | −0.0036 (4) |
C10 | 0.0488 (7) | 0.0226 (5) | 0.0414 (6) | −0.0020 (4) | 0.0134 (5) | 0.0008 (4) |
C11 | 0.0400 (6) | 0.0243 (5) | 0.0436 (6) | −0.0009 (4) | 0.0147 (5) | 0.0002 (4) |
C12 | 0.0325 (5) | 0.0254 (5) | 0.0428 (6) | −0.0014 (4) | 0.0078 (4) | 0.0045 (4) |
C13 | 0.0465 (7) | 0.0399 (7) | 0.0572 (8) | −0.0055 (5) | 0.0120 (6) | −0.0107 (6) |
C14 | 0.0528 (9) | 0.0442 (8) | 0.0908 (12) | −0.0123 (6) | 0.0087 (8) | −0.0202 (8) |
C15 | 0.0391 (7) | 0.0390 (7) | 0.1101 (14) | −0.0085 (6) | 0.0165 (8) | 0.0043 (8) |
C16 | 0.0417 (7) | 0.0420 (7) | 0.0798 (10) | −0.0007 (5) | 0.0249 (7) | 0.0154 (7) |
C17 | 0.0395 (6) | 0.0357 (6) | 0.0499 (7) | −0.0009 (5) | 0.0141 (5) | 0.0078 (5) |
O4 | 0.0384 (5) | 0.0451 (5) | 0.0777 (7) | −0.0076 (4) | 0.0225 (5) | 0.0028 (5) |
O5 | 0.0853 (8) | 0.0354 (5) | 0.0489 (5) | 0.0014 (5) | 0.0047 (5) | −0.0069 (4) |
O6 | 0.0824 (7) | 0.0286 (4) | 0.0572 (6) | 0.0155 (5) | 0.0082 (5) | −0.0022 (4) |
N3 | 0.0339 (5) | 0.0229 (4) | 0.0435 (5) | −0.0003 (3) | 0.0113 (4) | 0.0007 (4) |
N4 | 0.0320 (5) | 0.0222 (4) | 0.0422 (5) | −0.0006 (3) | 0.0073 (4) | −0.0005 (3) |
C18 | 0.0293 (5) | 0.0269 (5) | 0.0363 (5) | −0.0009 (4) | 0.0076 (4) | −0.0039 (4) |
C19 | 0.0375 (6) | 0.0332 (6) | 0.0516 (7) | 0.0044 (5) | 0.0098 (5) | −0.0073 (5) |
C20 | 0.0351 (6) | 0.0536 (8) | 0.0558 (8) | 0.0071 (6) | 0.0134 (6) | −0.0111 (6) |
C21 | 0.0349 (6) | 0.0585 (8) | 0.0574 (8) | −0.0066 (6) | 0.0175 (6) | −0.0038 (6) |
C22 | 0.0367 (6) | 0.0379 (6) | 0.0508 (7) | −0.0081 (5) | 0.0108 (5) | 0.0003 (5) |
C23 | 0.0307 (5) | 0.0277 (5) | 0.0368 (5) | −0.0021 (4) | 0.0066 (4) | −0.0029 (4) |
C24 | 0.0330 (5) | 0.0247 (5) | 0.0374 (5) | −0.0002 (4) | 0.0060 (4) | 0.0017 (4) |
C25 | 0.0333 (6) | 0.0304 (5) | 0.0420 (6) | −0.0012 (4) | 0.0028 (5) | −0.0040 (4) |
C26 | 0.0317 (5) | 0.0265 (5) | 0.0486 (6) | −0.0037 (4) | 0.0113 (5) | −0.0060 (4) |
C27 | 0.0477 (7) | 0.0244 (5) | 0.0407 (6) | 0.0005 (4) | 0.0115 (5) | 0.0005 (4) |
C28 | 0.0442 (6) | 0.0246 (5) | 0.0453 (6) | 0.0000 (4) | 0.0167 (5) | −0.0006 (4) |
C29 | 0.0325 (5) | 0.0253 (5) | 0.0455 (6) | 0.0008 (4) | 0.0098 (5) | 0.0031 (4) |
C30 | 0.0370 (6) | 0.0347 (6) | 0.0468 (7) | 0.0028 (5) | 0.0067 (5) | 0.0025 (5) |
C31 | 0.0379 (7) | 0.0410 (7) | 0.0612 (8) | 0.0079 (5) | 0.0070 (6) | 0.0076 (6) |
C32 | 0.0493 (8) | 0.0383 (7) | 0.0730 (9) | 0.0120 (6) | 0.0218 (7) | 0.0007 (6) |
C33 | 0.0529 (8) | 0.0469 (8) | 0.0533 (8) | 0.0097 (6) | 0.0148 (6) | −0.0072 (6) |
C34 | 0.0410 (7) | 0.0389 (6) | 0.0464 (7) | 0.0058 (5) | 0.0090 (5) | −0.0013 (5) |
O1—C9 | 1.2162 (14) | O4—C26 | 1.2127 (14) |
O2—C11 | 1.3157 (14) | O5—C28 | 1.1952 (16) |
O2—H2A | 0.8200 | O6—C28 | 1.3141 (15) |
O3—C11 | 1.1996 (15) | O6—H6 | 0.8200 |
N1—C9 | 1.3737 (14) | N3—C26 | 1.3732 (14) |
N1—C1 | 1.4197 (14) | N3—C18 | 1.4197 (14) |
N1—C10 | 1.4593 (14) | N3—C27 | 1.4582 (14) |
N2—C7 | 1.2868 (14) | N4—C24 | 1.2885 (14) |
N2—C6 | 1.4159 (14) | N4—C23 | 1.4175 (14) |
C1—C2 | 1.3983 (16) | C18—C19 | 1.4022 (16) |
C1—C6 | 1.4094 (15) | C18—C23 | 1.4060 (15) |
C2—C3 | 1.382 (2) | C19—C20 | 1.3750 (19) |
C2—H2 | 0.967 (17) | C19—H19 | 0.986 (16) |
C3—C4 | 1.382 (2) | C20—C21 | 1.387 (2) |
C3—H3 | 0.980 (16) | C20—H20 | 0.967 (17) |
C4—C5 | 1.3808 (19) | C21—C22 | 1.3807 (19) |
C4—H4 | 0.989 (16) | C21—H21 | 1.039 (15) |
C5—C6 | 1.3984 (16) | C22—C23 | 1.3959 (16) |
C5—H5 | 0.999 (15) | C22—H22 | 1.021 (15) |
C7—C12 | 1.4823 (15) | C24—C29 | 1.4822 (15) |
C7—C8 | 1.5034 (15) | C24—C25 | 1.5097 (15) |
C8—C9 | 1.5066 (16) | C25—C26 | 1.5139 (17) |
C8—H8A | 0.975 (14) | C25—H25A | 0.983 (14) |
C8—H8B | 1.012 (14) | C25—H25B | 0.959 (15) |
C10—C11 | 1.5198 (15) | C27—C28 | 1.5176 (15) |
C10—H10A | 0.916 (14) | C27—H27A | 0.941 (15) |
C10—H10B | 0.978 (15) | C27—H27B | 0.921 (14) |
C12—C13 | 1.3906 (17) | C29—C34 | 1.3915 (17) |
C12—C17 | 1.3952 (17) | C29—C30 | 1.3995 (16) |
C13—C14 | 1.391 (2) | C30—C31 | 1.3832 (18) |
C13—H13 | 0.964 (16) | C30—H30 | 0.988 (16) |
C14—C15 | 1.365 (3) | C31—C32 | 1.384 (2) |
C14—H14 | 0.96 (3) | C31—H31 | 0.972 (15) |
C15—C16 | 1.376 (2) | C32—C33 | 1.381 (2) |
C15—H15 | 0.991 (18) | C32—H32 | 0.974 (19) |
C16—C17 | 1.3870 (18) | C33—C34 | 1.3838 (18) |
C16—H16 | 0.901 (19) | C33—H33 | 0.933 (18) |
C17—H17 | 1.004 (17) | C34—H34 | 1.031 (16) |
C11—O2—H2A | 109.5 | C28—O6—H6 | 109.5 |
C9—N1—C1 | 123.54 (9) | C26—N3—C18 | 123.59 (9) |
C9—N1—C10 | 114.51 (9) | C26—N3—C27 | 116.85 (10) |
C1—N1—C10 | 120.19 (9) | C18—N3—C27 | 119.02 (9) |
C7—N2—C6 | 120.58 (9) | C24—N4—C23 | 120.87 (9) |
C2—C1—C6 | 118.21 (10) | C19—C18—C23 | 118.77 (10) |
C2—C1—N1 | 119.56 (10) | C19—C18—N3 | 119.26 (10) |
C6—C1—N1 | 122.20 (9) | C23—C18—N3 | 121.78 (9) |
C3—C2—C1 | 121.29 (12) | C20—C19—C18 | 121.14 (12) |
C3—C2—H2 | 116.4 (9) | C20—C19—H19 | 118.2 (9) |
C1—C2—H2 | 122.3 (9) | C18—C19—H19 | 120.6 (9) |
C4—C3—C2 | 120.36 (12) | C19—C20—C21 | 120.18 (12) |
C4—C3—H3 | 118.0 (10) | C19—C20—H20 | 121.4 (10) |
C2—C3—H3 | 121.6 (10) | C21—C20—H20 | 118.4 (10) |
C5—C4—C3 | 119.48 (12) | C22—C21—C20 | 119.50 (12) |
C5—C4—H4 | 120.6 (9) | C22—C21—H21 | 117.3 (8) |
C3—C4—H4 | 120.0 (9) | C20—C21—H21 | 123.1 (8) |
C4—C5—C6 | 121.10 (12) | C21—C22—C23 | 121.36 (12) |
C4—C5—H5 | 121.2 (8) | C21—C22—H22 | 122.9 (8) |
C6—C5—H5 | 117.7 (8) | C23—C22—H22 | 115.7 (8) |
C5—C6—C1 | 119.55 (10) | C22—C23—C18 | 119.04 (10) |
C5—C6—N2 | 115.48 (10) | C22—C23—N4 | 116.45 (10) |
C1—C6—N2 | 124.88 (10) | C18—C23—N4 | 124.34 (9) |
N2—C7—C12 | 119.32 (10) | N4—C24—C29 | 119.33 (10) |
N2—C7—C8 | 120.71 (10) | N4—C24—C25 | 120.72 (10) |
C12—C7—C8 | 119.97 (10) | C29—C24—C25 | 119.86 (10) |
C7—C8—C9 | 107.81 (9) | C24—C25—C26 | 105.68 (9) |
C7—C8—H8A | 113.3 (8) | C24—C25—H25A | 109.1 (8) |
C9—C8—H8A | 106.8 (8) | C26—C25—H25A | 107.9 (8) |
C7—C8—H8B | 111.1 (8) | C24—C25—H25B | 111.6 (9) |
C9—C8—H8B | 110.1 (8) | C26—C25—H25B | 110.2 (9) |
H8A—C8—H8B | 107.6 (11) | H25A—C25—H25B | 112.1 (12) |
O1—C9—N1 | 121.89 (11) | O4—C26—N3 | 122.33 (11) |
O1—C9—C8 | 122.57 (11) | O4—C26—C25 | 122.79 (11) |
N1—C9—C8 | 115.54 (10) | N3—C26—C25 | 114.83 (10) |
N1—C10—C11 | 111.34 (10) | N3—C27—C28 | 112.49 (10) |
N1—C10—H10A | 109.3 (9) | N3—C27—H27A | 107.5 (9) |
C11—C10—H10A | 108.5 (9) | C28—C27—H27A | 109.8 (9) |
N1—C10—H10B | 109.2 (9) | N3—C27—H27B | 110.5 (9) |
C11—C10—H10B | 110.3 (9) | C28—C27—H27B | 107.1 (9) |
H10A—C10—H10B | 108.2 (13) | H27A—C27—H27B | 109.5 (12) |
O3—C11—O2 | 124.60 (10) | O5—C28—O6 | 125.06 (11) |
O3—C11—C10 | 123.72 (10) | O5—C28—C27 | 124.04 (11) |
O2—C11—C10 | 111.66 (10) | O6—C28—C27 | 110.90 (10) |
C13—C12—C17 | 118.80 (11) | C34—C29—C30 | 118.83 (11) |
C13—C12—C7 | 120.07 (11) | C34—C29—C24 | 120.63 (10) |
C17—C12—C7 | 121.11 (11) | C30—C29—C24 | 120.54 (10) |
C12—C13—C14 | 119.55 (14) | C31—C30—C29 | 120.31 (12) |
C12—C13—H13 | 120.0 (10) | C31—C30—H30 | 120.7 (9) |
C14—C13—H13 | 120.4 (10) | C29—C30—H30 | 119.0 (9) |
C15—C14—C13 | 121.18 (15) | C30—C31—C32 | 120.29 (12) |
C15—C14—H14 | 122.6 (14) | C30—C31—H31 | 119.6 (9) |
C13—C14—H14 | 116.1 (14) | C32—C31—H31 | 120.1 (9) |
C14—C15—C16 | 119.92 (13) | C33—C32—C31 | 119.74 (13) |
C14—C15—H15 | 119.8 (10) | C33—C32—H32 | 121.2 (11) |
C16—C15—H15 | 120.3 (10) | C31—C32—H32 | 119.1 (11) |
C15—C16—C17 | 119.95 (15) | C32—C33—C34 | 120.44 (13) |
C15—C16—H16 | 122.8 (12) | C32—C33—H33 | 121.2 (10) |
C17—C16—H16 | 117.2 (12) | C34—C33—H33 | 118.4 (10) |
C16—C17—C12 | 120.56 (13) | C33—C34—C29 | 120.39 (12) |
C16—C17—H17 | 117.7 (9) | C33—C34—H34 | 118.0 (9) |
C12—C17—H17 | 121.7 (9) | C29—C34—H34 | 121.5 (9) |
C9—N1—C1—C2 | −137.08 (12) | C26—N3—C18—C19 | 137.80 (11) |
C10—N1—C1—C2 | 26.96 (16) | C27—N3—C18—C19 | −33.44 (15) |
C9—N1—C1—C6 | 45.09 (16) | C26—N3—C18—C23 | −47.32 (16) |
C10—N1—C1—C6 | −150.87 (11) | C27—N3—C18—C23 | 141.44 (11) |
C6—C1—C2—C3 | −1.79 (18) | C23—C18—C19—C20 | −0.59 (18) |
N1—C1—C2—C3 | −179.70 (12) | N3—C18—C19—C20 | 174.44 (11) |
C1—C2—C3—C4 | 0.9 (2) | C18—C19—C20—C21 | 0.6 (2) |
C2—C3—C4—C5 | 0.7 (2) | C19—C20—C21—C22 | −0.4 (2) |
C3—C4—C5—C6 | −1.4 (2) | C20—C21—C22—C23 | 0.3 (2) |
C4—C5—C6—C1 | 0.39 (19) | C21—C22—C23—C18 | −0.37 (18) |
C4—C5—C6—N2 | 177.02 (12) | C21—C22—C23—N4 | −175.85 (12) |
C2—C1—C6—C5 | 1.16 (17) | C19—C18—C23—C22 | 0.49 (16) |
N1—C1—C6—C5 | 179.02 (11) | N3—C18—C23—C22 | −174.42 (10) |
C2—C1—C6—N2 | −175.12 (11) | C19—C18—C23—N4 | 175.58 (10) |
N1—C1—C6—N2 | 2.73 (18) | N3—C18—C23—N4 | 0.67 (17) |
C7—N2—C6—C5 | 138.67 (11) | C24—N4—C23—C22 | −141.09 (11) |
C7—N2—C6—C1 | −44.91 (17) | C24—N4—C23—C18 | 43.70 (16) |
C6—N2—C7—C12 | 178.79 (9) | C23—N4—C24—C29 | −175.62 (10) |
C6—N2—C7—C8 | −0.99 (16) | C23—N4—C24—C25 | 0.86 (16) |
N2—C7—C8—C9 | 73.67 (13) | N4—C24—C25—C26 | −74.56 (13) |
C12—C7—C8—C9 | −106.11 (11) | C29—C24—C25—C26 | 101.89 (11) |
C1—N1—C9—O1 | 175.41 (11) | C18—N3—C26—O4 | −178.32 (11) |
C10—N1—C9—O1 | 10.55 (16) | C27—N3—C26—O4 | −6.90 (16) |
C1—N1—C9—C8 | −5.74 (15) | C18—N3—C26—C25 | 4.16 (15) |
C10—N1—C9—C8 | −170.60 (9) | C27—N3—C26—C25 | 175.58 (9) |
C7—C8—C9—O1 | 111.79 (13) | C24—C25—C26—O4 | −108.08 (13) |
C7—C8—C9—N1 | −67.04 (12) | C24—C25—C26—N3 | 69.43 (12) |
C9—N1—C10—C11 | 72.77 (13) | C26—N3—C27—C28 | −81.33 (13) |
C1—N1—C10—C11 | −92.65 (13) | C18—N3—C27—C28 | 90.50 (13) |
N1—C10—C11—O3 | 17.87 (18) | N3—C27—C28—O5 | 21.02 (18) |
N1—C10—C11—O2 | −163.44 (10) | N3—C27—C28—O6 | −159.08 (11) |
N2—C7—C12—C13 | −27.62 (16) | N4—C24—C29—C34 | 36.54 (16) |
C8—C7—C12—C13 | 152.16 (11) | C25—C24—C29—C34 | −139.96 (12) |
N2—C7—C12—C17 | 150.59 (11) | N4—C24—C29—C30 | −142.93 (11) |
C8—C7—C12—C17 | −29.63 (15) | C25—C24—C29—C30 | 40.57 (15) |
C17—C12—C13—C14 | −1.80 (19) | C34—C29—C30—C31 | −0.92 (18) |
C7—C12—C13—C14 | 176.45 (13) | C24—C29—C30—C31 | 178.56 (11) |
C12—C13—C14—C15 | 0.0 (2) | C29—C30—C31—C32 | 0.5 (2) |
C13—C14—C15—C16 | 1.3 (3) | C30—C31—C32—C33 | 0.1 (2) |
C14—C15—C16—C17 | −0.6 (2) | C31—C32—C33—C34 | −0.2 (2) |
C15—C16—C17—C12 | −1.2 (2) | C32—C33—C34—C29 | −0.2 (2) |
C13—C12—C17—C16 | 2.43 (18) | C30—C29—C34—C33 | 0.81 (19) |
C7—C12—C17—C16 | −175.80 (11) | C24—C29—C34—C33 | −178.67 (12) |
Cg1 and Cg2 are the centroids of the C18–C22 and C29–C34 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2A···N4 | 0.82 | 1.90 | 2.7161 (12) | 176 |
O6—H6···N2i | 0.82 | 1.95 | 2.7585 (13) | 171 |
C4—H4···Cg2ii | 0.989 (16) | 2.97 (2) | 3.7650 (16) | 139 (1) |
C17—H17···Cg1iii | 1.004 (17) | 2.82 (2) | 3.6431 (14) | 140 (1) |
Symmetry codes: (i) x, y+1, z; (ii) −x+2, y−1/2, −z+1/2; (iii) x, −y+1/2, z+1/2. |
Acknowledgements
JTM thanks Tulane University for support of the Tulane Crystallography Laboratory.
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