3-{[3-(4-Meth­oxy­phen­yl)-4,5-dihydro-1,2-oxazol-5-yl]meth­yl}-1,5-dimethyl-1H-1,5-benzodiazepine-2,4(3H,5H)-dione

Dardouri, R.; Rodi, Y.K.; Saffon, N.; Essassi, E.M.; Ng, S.W.

doi:10.1107/S1600536811022872

organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page o1729

doi:10.1107/S1600536811022872

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3-{[3-(4-Methoxyphenyl)-4,5-dihydro-1,2-oxazol-5-yl]methyl}-1,5-dimethyl-1H-1,5-benzodiazepine-2,4(3H,5H)-dione

Rachida Dardouri,^a Yousef Kandri Rodi,^a Natalie Saffon,^b El Mokhtar Essassi ^c and Seik Weng Ng ^d ^*

^aLaboratoire de Chimie Organique Appliquée, Faculté des Sciences et Techniques, Université Sidi Mohamed Ben Abdallah, Fés, Morocco, ^bService Commun Rayons-X FR2599, Université Paul Sabatier Bâtiment 2R1, 118 route de Narbonne, Toulouse, France, ^cLaboratoire de Chimie Organique Hétérocyclique, Pôle de Compétences Pharmacochimie, Université Mohammed V-Agdal, BP 1014 Avenue Ibn Batout, Rabat, Morocco, and ^dDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 12 June 2011; accepted 13 June 2011; online 18 June 2011)

The molecule of the title compound, C₂₂H₂₃N₃O₄, features a benzodiazepine fused-ring system whose seven-membered ring adopts a boat-shaped conformation (with the C atoms of the fused-ring as the stern and the methine C atom as the prow). The methylene C atom connected to the methine C atom occupies an equatorial position. The methylene C atom is connected to the five-membered oxazole ring, both of which are disordered over two positions in a 0.634 (4):0.366 (4) ratio. Weak intermolecular C—H⋯O hydrogen bonding is present in the crystal structure.

Related literature

For a related compound, 1,5-dimethyl-3-[(3-phenyl-4,5-dihydro-1,2-oxazol-5-yl)methyl]-1H-1,5-benzodiazepine-2,4(3H,5H)-dione, see: Dardouri et al. (2010 ).

Experimental

Crystal data

C₂₂H₂₃N₃O₄
M_r = 393.43
Monoclinic, C 2/c
a = 28.0041 (5) Å
b = 15.4644 (3) Å
c = 9.0350 (2) Å
β = 93.235 (1)°
V = 3906.52 (13) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.40 × 0.05 × 0.05 mm

Data collection

Bruker APEXII diffractometer
30861 measured reflections
3445 independent reflections
2548 reflections with I > 2σ(I)
R_int = 0.047

Refinement

R[F² > 2σ(F²)] = 0.061
wR(F²) = 0.179
S = 1.05
3445 reflections
272 parameters
41 restraints
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O3ⁱ	0.93	2.51	3.367 (7)	154
C11—H11B⋯O1ⁱⁱ	0.96	2.56	3.501 (5)	168
Symmetry codes: (i) $[-x+{\script{3\over 2}}, -y+{\script{1\over 2}}, -z]$ ; (ii) $[-x+{\script{3\over 2}}, -y+{\script{1\over 2}}, -z+1]$ .

Data collection: APEX2 (Bruker, 2005 ); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811022872/xu5243sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811022872/xu5243Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811022872/xu5243Isup3.cml

checkCIF report

Comment top

A previous study reported the structure of 1,5-dimethyl-3-[(3-phenyl-1,2-oxazol-5-yl)methyl]-1,5-benzodiazepine-2,4-dione (Dardouri et al., 2010). The phenyl group in this compound is replaced by an anisyl group in the title compound (Scheme I). The molecule of C₂₂H₂₃N₃O₄ features a benzodiazepine fused-ring whose seven-membered ring adopts a boat-shaped conformation (with the C atoms of the fused-ring as the stern and the methine C atom as the prow). The methylene C atom connected to the methine C atom occupies an equatorial position (Fig. 1).

Related literature top

For a related compound, 1,5-dimethyl-3-[(3-phenyl-4,5-dihydro-1,2-oxazol-5-yl)methyl]-1H-1,5-benzodiazepine-2,4(3H,5H)-dione, see: Dardouri et al. (2010).

Experimental top

To a solution of 3-allyl-1,5-dimethyl-1,5-benzodiazepine-2,4-dione (0.25 g, 1 mmol) and 4-methoxybenzaldoxime (0.2 g, 1.3 mmol) in chloroform (10 ml) was added at 0°C a solution of 24% bleach (4 ml). Stirring was continued for 4 h. The organic layer was dried over sodium sulfate and the solvent evaporated under reduced pressure. The residue was then purified by column chromatography on silica gel by using a mixture of hexane and ethyl acetate (1/1) as eluent. Colorless crystals were isolated when solvent was allowed to evaporate.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C₂₂H₂₃N₃O₄ at the 50% probability level; hydrogen atoms are drawn as arbitrary radius. The disorder is not shown.

3-{[3-(4-Methoxyphenyl)-4,5-dihydro-1,2-oxazol-5-yl]methyl}- 1,5-dimethyl-1H-1,5-benzodiazepine-2,4(3H,5H)-dione top

Crystal data top

C₂₂H₂₃N₃O₄	F(000) = 1664
M_r = 393.43	D_x = 1.338 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 5272 reflections
a = 28.0041 (5) Å	θ = 2.6–21.8°
b = 15.4644 (3) Å	µ = 0.09 mm⁻¹
c = 9.0350 (2) Å	T = 293 K
β = 93.235 (1)°	Prism, colorless
V = 3906.52 (13) Å³	0.40 × 0.05 × 0.05 mm
Z = 8

Data collection top

Bruker APEXII diffractometer	2548 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.047
Graphite monochromator	θ_max = 25.0°, θ_min = 1.5°
ϕ and ω scans	h = −33→31
30861 measured reflections	k = −18→18
3445 independent reflections	l = −10→10

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.061	H-atom parameters constrained
wR(F²) = 0.179	w = 1/[σ²(F_o²) + (0.0764P)² + 5.3445P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.001
3445 reflections	Δρ_max = 0.31 e Å⁻³
272 parameters	Δρ_min = −0.27 e Å⁻³
41 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0013 (3)

Crystal data top

C₂₂H₂₃N₃O₄	V = 3906.52 (13) Å³
M_r = 393.43	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 28.0041 (5) Å	µ = 0.09 mm⁻¹
b = 15.4644 (3) Å	T = 293 K
c = 9.0350 (2) Å	0.40 × 0.05 × 0.05 mm
β = 93.235 (1)°

Data collection top

Bruker APEXII diffractometer	2548 reflections with I > 2σ(I)
30861 measured reflections	R_int = 0.047
3445 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.061	41 restraints
wR(F²) = 0.179	H-atom parameters constrained
S = 1.05	Δρ_max = 0.31 e Å⁻³
3445 reflections	Δρ_min = −0.27 e Å⁻³
272 parameters

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.67566 (10)	0.19618 (16)	0.5304 (3)	0.0852 (8)
O2	0.57207 (8)	0.11159 (17)	0.2866 (3)	0.0770 (7)
O3	0.63939 (16)	0.3964 (3)	0.2387 (4)	0.0605 (14)	0.634 (4)
O4	0.54628 (8)	0.85003 (14)	0.3904 (3)	0.0710 (7)
N1	0.71472 (9)	0.14146 (16)	0.3388 (3)	0.0578 (7)
N2	0.63531 (8)	0.07484 (15)	0.1556 (3)	0.0536 (6)
N3	0.6331 (2)	0.4866 (4)	0.2330 (7)	0.060 (2)	0.634 (4)
C1	0.67932 (11)	0.09694 (18)	0.0955 (3)	0.0523 (7)
C2	0.68467 (17)	0.0844 (3)	−0.0552 (4)	0.0855 (12)
H2	0.6590	0.0641	−0.1152	0.103*
C3	0.7269 (3)	0.1015 (3)	−0.1157 (6)	0.119 (2)
H3	0.7296	0.0928	−0.2167	0.143*
C4	0.7656 (2)	0.1314 (3)	−0.0313 (7)	0.117 (2)
H4	0.7946	0.1413	−0.0738	0.141*
C5	0.76090 (14)	0.1467 (2)	0.1191 (5)	0.0880 (13)
H5	0.7865	0.1691	0.1768	0.106*
C6	0.71793 (11)	0.12863 (18)	0.1834 (3)	0.0542 (8)
C7	0.61090 (12)	−0.0048 (2)	0.1047 (4)	0.0737 (10)
H7A	0.5898	−0.0238	0.1783	0.111*
H7B	0.6342	−0.0489	0.0892	0.111*
H7C	0.5928	0.0064	0.0134	0.111*
C8	0.61146 (11)	0.1295 (2)	0.2423 (3)	0.0554 (8)
C9	0.63728 (13)	0.21183 (18)	0.2874 (4)	0.0650 (9)
H9	0.6512	0.2368	0.1999	0.078*	0.634 (4)
H9'	0.6510	0.2375	0.2002	0.078*	0.366 (4)
C10	0.67758 (12)	0.18422 (18)	0.3971 (4)	0.0602 (8)
C11	0.75503 (13)	0.1155 (3)	0.4405 (5)	0.0895 (12)
H11A	0.7430	0.0928	0.5300	0.134*
H11B	0.7749	0.1648	0.4635	0.134*
H11C	0.7735	0.0718	0.3942	0.134*
C12	0.59677 (16)	0.2732 (3)	0.3369 (6)	0.0481 (11)	0.634 (4)
H12A	0.5712	0.2755	0.2599	0.058*	0.634 (4)
H12B	0.5836	0.2506	0.4261	0.058*	0.634 (4)
C13	0.61609 (16)	0.3625 (3)	0.3660 (5)	0.0512 (10)	0.634 (4)
H13	0.6381	0.3630	0.4544	0.061*	0.634 (4)
C14	0.57479 (7)	0.42592 (11)	0.3838 (2)	0.0855 (13)	0.634 (4)
H14A	0.5455	0.4069	0.3312	0.103*	0.634 (4)
H14B	0.5690	0.4365	0.4870	0.103*	0.634 (4)
C15	0.59627 (7)	0.50273 (11)	0.3118 (2)	0.0683 (10)
C16	0.58267 (7)	0.59290 (11)	0.3351 (2)	0.0551 (8)
C17	0.54373 (7)	0.61376 (11)	0.4159 (2)	0.0683 (10)
H17	0.5262	0.5696	0.4569	0.082*
C18	0.53026 (11)	0.6984 (2)	0.4372 (3)	0.0610 (8)
H18	0.5038	0.7110	0.4911	0.073*
C19	0.55629 (10)	0.76409 (19)	0.3782 (3)	0.0533 (7)
C20	0.59550 (10)	0.7442 (2)	0.2959 (3)	0.0551 (7)
H20	0.6132	0.7884	0.2555	0.066*
C21	0.60796 (10)	0.6603 (2)	0.2746 (3)	0.0547 (7)
H21	0.6339	0.6478	0.2185	0.066*
C22	0.50391 (11)	0.8728 (2)	0.4642 (5)	0.0783 (11)
H22A	0.5006	0.9346	0.4656	0.117*
H22B	0.5064	0.8514	0.5640	0.117*
H22C	0.4765	0.8477	0.4121	0.117*
O3'	0.6240 (3)	0.3830 (6)	0.1858 (9)	0.0605 (14)	0.37
N3'	0.6197 (5)	0.4734 (7)	0.2005 (15)	0.060 (2)	0.37
C12'	0.6199 (3)	0.2846 (5)	0.3878 (9)	0.0481 (11)	0.37
H12C	0.6000	0.2615	0.4631	0.058*	0.366 (4)
H12D	0.6467	0.3151	0.4360	0.058*	0.366 (4)
C13'	0.5914 (3)	0.3432 (4)	0.2836 (8)	0.0512 (10)	0.37
H13'	0.5647	0.3136	0.2302	0.061*	0.366 (4)
C14'	0.5746 (4)	0.4238 (4)	0.3791 (12)	0.0855 (13)	0.37
H14C	0.5400	0.4280	0.3741	0.103*	0.366 (4)
H14D	0.5858	0.4176	0.4821	0.103*	0.366 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.125 (2)	0.0719 (16)	0.0621 (15)	−0.0375 (15)	0.0306 (14)	−0.0213 (12)
O2	0.0500 (13)	0.1008 (19)	0.0811 (16)	0.0140 (12)	0.0119 (11)	0.0077 (13)
O3	0.067 (3)	0.046 (2)	0.071 (3)	0.0145 (19)	0.034 (2)	0.000 (2)
O4	0.0630 (14)	0.0528 (13)	0.0976 (17)	0.0060 (10)	0.0090 (12)	−0.0198 (12)
N1	0.0545 (15)	0.0564 (15)	0.0630 (16)	−0.0168 (12)	0.0066 (12)	−0.0010 (12)
N2	0.0506 (14)	0.0556 (14)	0.0545 (14)	0.0116 (11)	0.0017 (11)	−0.0023 (11)
N3	0.067 (4)	0.045 (2)	0.072 (4)	0.010 (2)	0.033 (4)	0.0050 (19)
C1	0.0648 (19)	0.0446 (15)	0.0486 (16)	0.0190 (13)	0.0136 (14)	0.0038 (12)
C2	0.126 (3)	0.081 (3)	0.053 (2)	0.042 (2)	0.025 (2)	0.0108 (17)
C3	0.181 (6)	0.096 (4)	0.088 (3)	0.058 (4)	0.087 (4)	0.031 (3)
C4	0.127 (4)	0.076 (3)	0.160 (5)	0.042 (3)	0.110 (4)	0.053 (3)
C5	0.073 (2)	0.067 (2)	0.129 (4)	0.0121 (18)	0.052 (2)	0.033 (2)
C6	0.0553 (17)	0.0432 (15)	0.0664 (19)	0.0068 (13)	0.0247 (15)	0.0113 (13)
C7	0.068 (2)	0.075 (2)	0.075 (2)	0.0031 (18)	−0.0172 (17)	−0.0143 (18)
C8	0.0539 (18)	0.0577 (18)	0.0556 (17)	0.0165 (14)	0.0106 (14)	0.0099 (14)
C9	0.090 (2)	0.0436 (16)	0.066 (2)	0.0164 (16)	0.0442 (18)	0.0085 (14)
C10	0.079 (2)	0.0416 (16)	0.063 (2)	−0.0227 (15)	0.0292 (17)	−0.0111 (14)
C11	0.074 (2)	0.091 (3)	0.100 (3)	−0.034 (2)	−0.025 (2)	−0.004 (2)
C12	0.044 (3)	0.048 (2)	0.053 (3)	0.008 (2)	0.011 (2)	−0.0026 (19)
C13	0.056 (3)	0.044 (2)	0.055 (3)	0.0088 (19)	0.0169 (18)	−0.0011 (18)
C14	0.102 (3)	0.058 (2)	0.103 (3)	0.0323 (19)	0.063 (2)	0.0215 (18)
C15	0.079 (2)	0.0585 (19)	0.072 (2)	0.0267 (16)	0.0420 (18)	0.0198 (16)
C16	0.0589 (18)	0.0555 (17)	0.0531 (16)	0.0217 (14)	0.0234 (14)	0.0109 (13)
C17	0.075 (2)	0.0589 (19)	0.075 (2)	0.0219 (16)	0.0391 (18)	0.0160 (16)
C18	0.0598 (18)	0.065 (2)	0.0611 (19)	0.0216 (15)	0.0241 (15)	0.0025 (15)
C19	0.0533 (17)	0.0530 (17)	0.0531 (16)	0.0093 (14)	−0.0001 (13)	−0.0071 (13)
C20	0.0471 (16)	0.0578 (18)	0.0612 (18)	0.0004 (14)	0.0097 (14)	−0.0044 (14)
C21	0.0491 (16)	0.0656 (19)	0.0509 (17)	0.0133 (14)	0.0148 (13)	−0.0001 (14)
C22	0.0513 (18)	0.066 (2)	0.117 (3)	0.0156 (16)	−0.0008 (19)	−0.034 (2)
O3'	0.067 (3)	0.046 (2)	0.071 (3)	0.0145 (19)	0.034 (2)	0.000 (2)
N3'	0.067 (4)	0.045 (2)	0.072 (4)	0.010 (2)	0.033 (4)	0.0050 (19)
C12'	0.044 (3)	0.048 (2)	0.053 (3)	0.008 (2)	0.011 (2)	−0.0026 (19)
C13'	0.056 (3)	0.044 (2)	0.055 (3)	0.0088 (19)	0.0169 (18)	−0.0011 (18)
C14'	0.102 (3)	0.058 (2)	0.103 (3)	0.0323 (19)	0.063 (2)	0.0215 (18)

Geometric parameters (Å, º) top

O1—C10	1.222 (4)	C11—H11C	0.9600
O2—C8	1.226 (3)	C12—C13	1.502 (6)
O3—N3	1.407 (5)	C12—H12A	0.9700
O3—C13	1.451 (5)	C12—H12B	0.9700
O4—C19	1.364 (3)	C13—C14	1.531 (4)
O4—C22	1.437 (4)	C13—H13	0.9800
N1—C10	1.364 (4)	C14—C15	1.4965
N1—C6	1.426 (4)	C14—H14A	0.9700
N1—C11	1.470 (4)	C14—H14B	0.9700
N2—C8	1.354 (4)	C15—N3'	1.313 (8)
N2—C1	1.416 (4)	C15—C16	1.4638
N2—C7	1.469 (4)	C15—C14'	1.507 (7)
N3—C15	1.309 (5)	C16—C17	1.3846
C1—C6	1.394 (4)	C16—C21	1.390 (3)
C1—C2	1.392 (4)	C17—C18	1.379 (3)
C2—C3	1.356 (7)	C17—H17	0.9300
C2—H2	0.9300	C18—C19	1.376 (4)
C3—C4	1.371 (8)	C18—H18	0.9300
C3—H3	0.9300	C19—C20	1.395 (4)
C4—C5	1.393 (7)	C20—C21	1.360 (4)
C4—H4	0.9300	C20—H20	0.9300
C5—C6	1.394 (4)	C21—H21	0.9300
C5—H5	0.9300	C22—H22A	0.9600
C7—H7A	0.9600	C22—H22B	0.9600
C7—H7B	0.9600	C22—H22C	0.9600
C7—H7C	0.9600	O3'—N3'	1.410 (8)
C8—C9	1.508 (5)	O3'—C13'	1.442 (8)
C9—C10	1.521 (5)	C12'—C13'	1.503 (8)
C9—C12'	1.541 (7)	C12'—H12C	0.9700
C9—C12	1.564 (5)	C12'—H12D	0.9700
C9—H9	0.9800	C13'—C14'	1.602 (8)
C9—H9'	0.9800	C13'—H13'	0.9800
C11—H11A	0.9600	C14'—H14C	0.9700
C11—H11B	0.9600	C14'—H14D	0.9700

N3—O3—C13	109.0 (4)	O3—C13—C12	111.5 (4)
C19—O4—C22	117.1 (3)	O3—C13—C14	103.2 (3)
C10—N1—C6	122.7 (3)	C12—C13—C14	109.9 (3)
C10—N1—C11	117.8 (3)	O3—C13—H13	110.7
C6—N1—C11	119.2 (3)	C12—C13—H13	110.7
C8—N2—C1	122.6 (3)	C14—C13—H13	110.7
C8—N2—C7	117.9 (3)	C15—C14—C13	97.93 (17)
C1—N2—C7	118.8 (2)	C15—C14—H14A	112.2
C15—N3—O3	105.6 (5)	C13—C14—H14A	112.2
C6—C1—C2	118.9 (3)	C15—C14—H14B	112.2
C6—C1—N2	122.0 (2)	C13—C14—H14B	112.2
C2—C1—N2	119.0 (3)	H14A—C14—H14B	109.8
C3—C2—C1	120.7 (5)	N3—C15—C16	118.6 (3)
C3—C2—H2	119.6	N3'—C15—C16	125.8 (5)
C1—C2—H2	119.6	N3—C15—C14	115.7 (3)
C2—C3—C4	121.5 (5)	N3'—C15—C14	106.8 (5)
C2—C3—H3	119.3	C16—C15—C14	125.4
C4—C3—H3	119.3	N3'—C15—C14'	105.1 (6)
C3—C4—C5	119.0 (4)	C16—C15—C14'	126.8 (3)
C3—C4—H4	120.5	C17—C16—C21	117.81 (13)
C5—C4—H4	120.5	C17—C16—C15	121.1
C4—C5—C6	120.3 (5)	C21—C16—C15	121.05 (13)
C4—C5—H5	119.9	C18—C17—C16	121.65 (14)
C6—C5—H5	119.9	C18—C17—H17	119.2
C1—C6—C5	119.5 (3)	C16—C17—H17	119.2
C1—C6—N1	121.3 (2)	C17—C18—C19	119.5 (2)
C5—C6—N1	119.1 (3)	C17—C18—H18	120.3
N2—C7—H7A	109.5	C19—C18—H18	120.3
N2—C7—H7B	109.5	O4—C19—C18	124.9 (3)
H7A—C7—H7B	109.5	O4—C19—C20	115.5 (3)
N2—C7—H7C	109.5	C18—C19—C20	119.6 (3)
H7A—C7—H7C	109.5	C21—C20—C19	120.1 (3)
H7B—C7—H7C	109.5	C21—C20—H20	119.9
O2—C8—N2	122.0 (3)	C19—C20—H20	119.9
O2—C8—C9	121.9 (3)	C20—C21—C16	121.3 (2)
N2—C8—C9	116.0 (3)	C20—C21—H21	119.3
C8—C9—C10	105.4 (2)	C16—C21—H21	119.3
C8—C9—C12'	127.7 (4)	O4—C22—H22A	109.5
C10—C9—C12'	93.9 (4)	O4—C22—H22B	109.5
C8—C9—C12	104.2 (3)	H22A—C22—H22B	109.5
C10—C9—C12	120.5 (3)	O4—C22—H22C	109.5
C8—C9—H9	108.7	H22A—C22—H22C	109.5
C10—C9—H9	108.7	H22B—C22—H22C	109.5
C12'—C9—H9	110.0	N3'—O3'—C13'	107.8 (8)
C12—C9—H9	108.7	C15—N3'—O3'	117.6 (9)
C8—C9—H9'	109.2	C13'—C12'—C9	104.2 (5)
C10—C9—H9'	109.2	C13'—C12'—H12C	110.9
C12'—C9—H9'	109.2	C9—C12'—H12C	110.9
C12—C9—H9'	107.9	C13'—C12'—H12D	110.9
O1—C10—N1	122.1 (3)	C9—C12'—H12D	110.9
O1—C10—C9	121.9 (3)	H12C—C12'—H12D	108.9
N1—C10—C9	116.0 (3)	O3'—C13'—C12'	108.1 (7)
N1—C11—H11A	109.5	O3'—C13'—C14'	102.4 (6)
N1—C11—H11B	109.5	C12'—C13'—C14'	107.1 (7)
H11A—C11—H11B	109.5	O3'—C13'—H13'	112.9
N1—C11—H11C	109.5	C12'—C13'—H13'	112.9
H11A—C11—H11C	109.5	C14'—C13'—H13'	112.9
H11B—C11—H11C	109.5	C15—C14'—C13'	105.9 (5)
C13—C12—C9	110.4 (3)	C15—C14'—H14D	110.5
C13—C12—H12A	109.6	C13'—C14'—H14D	110.5
C9—C12—H12A	109.6	C15—C14'—H14C	110.5
C13—C12—H12B	109.6	C13'—C14'—H14D	110.5
C9—C12—H12B	109.6	H14C—C14'—H14D	108.7
H12A—C12—H12B	108.1

C13—O3—N3—C15	−20.5 (6)	C12—C13—C14—C15	−144.4 (3)
C8—N2—C1—C6	51.7 (4)	O3—N3—C15—N3'	−69 (2)
C7—N2—C1—C6	−137.7 (3)	O3—N3—C15—C16	176.0 (3)
C8—N2—C1—C2	−130.1 (3)	O3—N3—C15—C14	2.1 (6)
C7—N2—C1—C2	40.5 (4)	O3—N3—C15—C14'	0.4 (8)
C6—C1—C2—C3	0.9 (5)	C13—C14—C15—N3	15.3 (4)
N2—C1—C2—C3	−177.3 (3)	C13—C14—C15—N3'	37.2 (8)
C1—C2—C3—C4	0.1 (7)	C13—C14—C15—C16	−158.1 (2)
C2—C3—C4—C5	−1.8 (7)	C13—C14—C15—C14'	66 (13)
C3—C4—C5—C6	2.5 (6)	N3—C15—C16—C17	179.2 (4)
C2—C1—C6—C5	−0.2 (4)	N3'—C15—C16—C17	154.3 (9)
N2—C1—C6—C5	178.0 (3)	C14—C15—C16—C17	−7.6
C2—C1—C6—N1	−179.0 (3)	C14'—C15—C16—C17	−5.8 (7)
N2—C1—C6—N1	−0.8 (4)	N3—C15—C16—C21	0.3 (4)
C4—C5—C6—C1	−1.5 (5)	N3'—C15—C16—C21	−24.6 (9)
C4—C5—C6—N1	177.4 (3)	C14—C15—C16—C21	173.52 (17)
C10—N1—C6—C1	−48.7 (4)	C14'—C15—C16—C21	175.2 (7)
C11—N1—C6—C1	137.5 (3)	C21—C16—C17—C18	−0.3 (2)
C10—N1—C6—C5	132.5 (3)	C15—C16—C17—C18	−179.28 (19)
C11—N1—C6—C5	−41.3 (4)	C16—C17—C18—C19	−0.6 (4)
C1—N2—C8—O2	175.7 (3)	C22—O4—C19—C18	−3.4 (4)
C7—N2—C8—O2	5.0 (4)	C22—O4—C19—C20	175.1 (3)
C1—N2—C8—C9	−7.3 (4)	C17—C18—C19—O4	179.3 (3)
C7—N2—C8—C9	−177.9 (3)	C17—C18—C19—C20	0.9 (5)
O2—C8—C9—C10	106.4 (3)	O4—C19—C20—C21	−178.8 (3)
N2—C8—C9—C10	−70.6 (3)	C18—C19—C20—C21	−0.2 (4)
O2—C8—C9—C12'	−1.3 (6)	C19—C20—C21—C16	−0.8 (4)
N2—C8—C9—C12'	−178.3 (4)	C17—C16—C21—C20	1.1 (3)
O2—C8—C9—C12	−21.4 (4)	C15—C16—C21—C20	−180.0 (2)
N2—C8—C9—C12	161.6 (3)	N3—C15—N3'—O3'	110 (3)
C6—N1—C10—O1	−178.6 (3)	C16—C15—N3'—O3'	−171.5 (8)
C11—N1—C10—O1	−4.8 (4)	C14—C15—N3'—O3'	−6.9 (14)
C6—N1—C10—C9	4.6 (4)	C14'—C15—N3'—O3'	−7.9 (15)
C11—N1—C10—C9	178.5 (3)	C13'—O3'—N3'—C15	12.3 (16)
C8—C9—C10—O1	−104.6 (3)	C8—C9—C12'—C13'	−87.0 (7)
C12'—C9—C10—O1	26.3 (5)	C10—C9—C12'—C13'	160.0 (6)
C12—C9—C10—O1	12.6 (4)	C12—C9—C12'—C13'	−44.5 (6)
C8—C9—C10—N1	72.1 (3)	N3'—O3'—C13'—C12'	−122.7 (10)
C12'—C9—C10—N1	−156.9 (4)	N3'—O3'—C13'—C14'	−9.9 (11)
C12—C9—C10—N1	−170.7 (3)	C9—C12'—C13'—O3'	−67.2 (8)
C8—C9—C12—C13	−172.4 (3)	C9—C12'—C13'—C14'	−176.8 (6)
C10—C9—C12—C13	69.8 (5)	N3—C15—C14'—C13'	−20.7 (10)
C12'—C9—C12—C13	41.0 (7)	N3'—C15—C14'—C13'	0.8 (12)
N3—O3—C13—C12	147.7 (5)	C16—C15—C14'—C13'	164.2 (4)
N3—O3—C13—C14	29.7 (5)	C14—C15—C14'—C13'	−151 (13)
C9—C12—C13—O3	54.9 (5)	O3'—C13'—C14'—C15	5.7 (10)
C9—C12—C13—C14	168.7 (3)	C12'—C13'—C14'—C15	119.3 (8)
O3—C13—C14—C15	−25.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O3ⁱ	0.93	2.51	3.367 (7)	154
C11—H11B···O1ⁱⁱ	0.96	2.56	3.501 (5)	168

Symmetry codes: (i) −x+3/2, −y+1/2, −z; (ii) −x+3/2, −y+1/2, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₂H₂₃N₃O₄
M_r	393.43
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	28.0041 (5), 15.4644 (3), 9.0350 (2)
β (°)	93.235 (1)
V (Å³)	3906.52 (13)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.40 × 0.05 × 0.05

Data collection
Diffractometer	Bruker APEXII diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	30861, 3445, 2548
R_int	0.047
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.061, 0.179, 1.05
No. of reflections	3445
No. of parameters	272
No. of restraints	41
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.27

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O3ⁱ	0.93	2.51	3.367 (7)	154
C11—H11B···O1ⁱⁱ	0.96	2.56	3.501 (5)	168

Symmetry codes: (i) −x+3/2, −y+1/2, −z; (ii) −x+3/2, −y+1/2, −z+1.

Acknowledgements

We thank Université Sidi Mohamed Ben Abdallah, Université Mohammed V-Agdal and the University of Malaya for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Dardouri, R., Kandri Rodi, Y., Saffon, N., El Ammari, L. & Essassi, E. M. (2010). Acta Cryst. E66, o2983. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 67| Part 7| July 2011| Page o1729

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

3-{[3-(4-Meth­­oxy­phen­yl)-4,5-di­hydro-1,2-oxazol-5-yl]meth­yl}-1,5-di­methyl-1H-1,5-benzodiazepine-2,4(3H,5H)-dione

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

3-{[3-(4-Methoxyphenyl)-4,5-dihydro-1,2-oxazol-5-yl]methyl}-1,5-dimethyl-1H-1,5-benzodiazepine-2,4(3H,5H)-dione