2-(2-Oxo-4-phenyl-2,3-di­hydro-1H-1,5-benzodiazepin-1-yl)acetic acid

Essaghouani, A.; Boulhaoua, M.; El Hafi, M.; Benchidmi, M.; Essassi, E.M.; Mague, J.T.

doi:10.1107/S2414314617001201

organic compounds

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ISSN: 2414-3146

Volume 2| Part 1| January 2017| x170120

https://doi.org/10.1107/S2414314617001201

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2-(2-Oxo-4-phenyl-2,3-dihydro-1H-1,5-benzodiazepin-1-yl)acetic acid

Abdelhanine Essaghouani,^a ^* Mohammed Boulhaoua,^a Mohamed El Hafi,^a Mohammed Benchidmi,^a El Mokhtar Essassi ^a and Joel T. Mague ^b

^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

Edited by R. J. Butcher, Howard University, USA (Received 23 December 2016; accepted 23 January 2017; online 27 January 2017)

The asymmetric unit of the title compound, C₁₇H₁₄N₂O₃, consists of two independent molecules having distinctly different conformations. The components of the asymmetric unit 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.

Keywords: crystal structure; hydrogen bond; 1,5-benzodiazepine; C—H⋯π(ring) interactions.

CCDC 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 asymmetric unit (Fig. 1) 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)°.

Figure 1
The asymmetric unit with the atom-labelling scheme and 50% probability ellipsoids. The O—H⋯N hydrogen bond is shown by the dotted line.

In 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).

Table 1
Hydrogen-bond geometry (Å, °)

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) $[-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Figure 2
Packing viewed along the c axis, with O—H⋯N hydrogen bonds shown as dotted lines.

Figure 3
Detail of the C—H⋯π(ring) interactions (dotted lines) [symmetry codes: (i) 2 − x, − $[{1\over 2}]$ + y, $[{1\over 2}]$ − z; (ii) x, $[{1\over 2}]$ − y, $[{1\over 2}]$ + z].

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 refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₇H₁₄N₂O₃
M_r	294.30
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	17.9752 (8), 17.4403 (8), 9.2472 (4)
β (°)	102.892 (1)
V (Å³)	2825.9 (2)
Z	8
Radiation type	Mo Kα
μ (mm⁻¹)	0.10
Crystal size (mm)	0.32 × 0.29 × 0.28

Data collection
Diffractometer	Bruker SMART APEX CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2016 )
T_min, T_max	0.89, 0.97
No. of measured, independent and observed [I > 2σ(I)] reflections	54166, 7627, 5791
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.687

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.146, 1.11
No. of reflections	7627
No. of parameters	503
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.21
Computer programs: APEX3 and SAINT (Bruker, 2016), SHELXT (Sheldrick, 2015a ), SHELXL2014 (Sheldrick, 2015b ), DIAMOND (Brandenburg & Putz, 2012 ) and SHELXTL (Sheldrick, 2008 ).

Structural data

CCDC reference: 1529295

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2414314617001201/bv4007sup1.cif

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

checkCIF report

Computing details top

Data collection: APEX3 (Bruker, 2016); cell refinement: 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).

2-(2-Oxo-4-phenyl-2,3-dihydro-1H-1,5-benzodiazepin-1-yl)acetic acid top

Crystal data top

C₁₇H₁₄N₂O₃	F(000) = 1232
M_r = 294.30	D_x = 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

Data collection top

Bruker SMART APEX CCD diffractometer	7627 independent reflections
Radiation source: fine-focus sealed tube	5791 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
Detector resolution: 8.3333 pixels mm^-1	θ_max = 29.2°, θ_min = 1.7°
φ and ω scans	h = −24→24
Absorption correction: multi-scan (SADABS; Bruker, 2016)	k = −23→23
T_min = 0.89, T_max = 0.97	l = −12→12
54166 measured reflections

Refinement top

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(F_o²) + (0.0941P)² + 0.0156P] where P = (F_o² + 2F_c²)/3
7627 reflections	(Δ/σ)_max = 0.001
503 parameters	Δρ_max = 0.36 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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.

References

Ballo, D., Ahabchane, N. H., Zouihri, H., Essassi, E. M. & Ng, S. W. (2010). Acta Cryst. E66, o2070. CrossRef IUCr Journals Google Scholar
Brandenburg, K. & Putz, H. (2012). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2016). APEX3, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Essaghouani, A., Bouzian, Y., Essassi, E. M., Saadi, M. & El Ammari, L. (2016). IUCrData, 1, x160661. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015a). Acta Cryst. A71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2015b). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar

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IUCrDATA

ISSN: 2414-3146

Volume 2| Part 1| January 2017| x170120

https://doi.org/10.1107/S2414314617001201

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

2-(2-Oxo-4-phenyl-2,3-di­hydro-1H-1,5-benzodiazepin-1-yl)acetic acid

Structure description

Synthesis and crystallization

Refinement

Structural data

Acknowledgements

References

organic compounds

2-(2-Oxo-4-phenyl-2,3-dihydro-1H-1,5-benzodiazepin-1-yl)acetic acid