1,5-Dimethyl-3-[(3-phenyl-4,5-dihydro-1,2-oxazol-5-yl)meth-yl]-1H-1,5-benzodiazepine-2,4(3H,5H)-dione.

The reaction of 3-allyl-1,5-dimethyl-1,5-benzodiazepine-2,4-dione and benzaldoxime leads to the title compound, C(21)H(21)N(3)O(3). The mol-ecular structure is built up from two fused six- and seven-membered rings linked to a chain including a five- and six-membered ring (isoxazoline and phen-yl) via a methyl-ene group. The seven-membered ring displays a boat conformation. The dihedral angle between the two six-membered rings is 74.3 (1)°.

Related literature

For the biological activity and pharmaceutical properties of benzodiazepines and their derivatives, see: Cherif Alaoui, et al. (2007 ▶); Fruscella et al. (2001 ▶); Guerrini et al. (2006 ▶); Jabli et al., (2009 ▶); Keita et al. (2003 ▶); Rajarao et al. (2007 ▶); Kalkhambkar et al. (2008 ▶); Poisbeau et al. (1997 ▶); Smith et al. (1998 ▶); Kotyatkina et al. (2001 ▶). For their reactivity, see: Kosychova et al. (2004 ▶); Nabih et al. (2003 ▶); Reddy et al. (2000 ▶).

Experimental

Crystal data

C21H21N3O3

M = 363.41

Monoclinic,

a = 9.3491 (2) Å

b = 6.9722 (1) Å

c = 27.9201 (5) Å

β = 93.157 (1)°

V = 1817.18 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.40 × 0.38 × 0.36 mm

Data collection

Bruker SMART CCD area-detector diffractometer

28704 measured reflections

3717 independent reflections

3261 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.148

S = 1.04

3717 reflections

246 parameters

H-atom parameters constrained

Δρmax = 0.49 e Å−3

Δρmin = −0.34 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia,1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810042972/im2239sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810042972/im2239Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C21H21N3O3	F(000) = 768
Mr = 363.41	Dx = 1.328 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 9929 reflections
a = 9.3491 (2) Å	θ = 2.9–30.5°
b = 6.9722 (1) Å	µ = 0.09 mm−1
c = 27.9201 (5) Å	T = 296 K
β = 93.157 (1)°	Block, colourless
V = 1817.18 (6) Å3	0.40 × 0.38 × 0.36 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	3261 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.031
graphite	θmax = 26.4°, θmin = 1.5°
phi and ω scans	h = −11→11
28704 measured reflections	k = −8→8
3717 independent reflections	l = −34→34

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.148	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.057P)2 + 1.9064P] where P = (Fo2 + 2Fc2)/3
3717 reflections	(Δ/σ)max < 0.001
246 parameters	Δρmax = 0.49 e Å−3
0 restraints	Δρmin = −0.34 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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.

	x	y	z	Uiso*/Ueq
O1	0.30152 (16)	0.5636 (3)	0.20375 (6)	0.0494 (4)
O2	0.22075 (18)	0.1345 (3)	0.12654 (6)	0.0491 (4)
O3	0.07230 (18)	0.6193 (3)	0.04335 (7)	0.0613 (6)
N1	0.07203 (18)	0.5003 (2)	0.22029 (6)	0.0325 (4)
N2	0.00716 (18)	0.1746 (2)	0.15947 (6)	0.0318 (4)
N3	0.1055 (2)	0.7758 (4)	0.01417 (8)	0.0563 (6)
C1	0.1419 (2)	0.4598 (3)	0.13807 (7)	0.0330 (4)
H1	0.0487	0.5157	0.1282	0.040*
C2	0.1802 (2)	0.5157 (3)	0.18989 (8)	0.0342 (5)
C3	−0.0714 (2)	0.4552 (3)	0.20444 (7)	0.0273 (4)
C4	−0.1840 (2)	0.5679 (3)	0.21943 (7)	0.0346 (5)
H4	−0.1645	0.6706	0.2400	0.042*
C5	−0.3242 (2)	0.5290 (3)	0.20406 (8)	0.0389 (5)
H5	−0.3982	0.6047	0.2145	0.047*
C6	−0.3540 (2)	0.3778 (3)	0.17330 (8)	0.0382 (5)
H6	−0.4480	0.3533	0.1624	0.046*
C7	−0.2445 (2)	0.2627 (3)	0.15860 (7)	0.0336 (4)
H7	−0.2655	0.1603	0.1381	0.040*
C8	−0.1026 (2)	0.2986 (3)	0.17428 (7)	0.0268 (4)
C9	0.1275 (2)	0.2418 (3)	0.13959 (7)	0.0334 (5)
C10	0.1040 (3)	0.5479 (4)	0.27119 (8)	0.0460 (6)
H10A	0.1908	0.4848	0.2824	0.069*
H10B	0.0266	0.5058	0.2898	0.069*
H10C	0.1155	0.6842	0.2746	0.069*
C11	−0.0081 (3)	−0.0331 (3)	0.16577 (10)	0.0479 (6)
H11A	0.0173	−0.0977	0.1371	0.072*
H11B	−0.1055	−0.0626	0.1721	0.072*
H11C	0.0540	−0.0749	0.1923	0.072*
C12	0.2525 (2)	0.5268 (4)	0.10382 (8)	0.0395 (5)
H12A	0.2736	0.6613	0.1097	0.047*
H12B	0.3404	0.4548	0.1099	0.047*
C13	0.2009 (2)	0.5008 (4)	0.05218 (8)	0.0435 (5)
H13	0.1786	0.3656	0.0457	0.052*
C14	0.3060 (3)	0.5754 (4)	0.01653 (8)	0.0454 (6)
H14A	0.3993	0.6017	0.0321	0.054*
H14B	0.3167	0.4856	−0.0096	0.054*
C15	0.2327 (2)	0.7564 (4)	−0.00061 (8)	0.0400 (5)
C16	0.2942 (2)	0.8996 (3)	−0.03233 (7)	0.0357 (5)
C17	0.2153 (2)	1.0624 (4)	−0.04645 (8)	0.0416 (5)
H17	0.1246	1.0817	−0.0352	0.050*
C18	0.2715 (2)	1.1944 (4)	−0.07698 (9)	0.0455 (6)
H18	0.2183	1.3021	−0.0863	0.055*
C19	0.4069 (2)	1.1680 (4)	−0.09397 (8)	0.0441 (5)
H19	0.4438	1.2569	−0.1148	0.053*
C20	0.4862 (2)	1.0094 (4)	−0.07983 (8)	0.0417 (5)
H20	0.5775	0.9920	−0.0908	0.050*
C21	0.4301 (2)	0.8760 (3)	−0.04936 (7)	0.0376 (5)
H21	0.4840	0.7689	−0.0401	0.045*

	U11	U22	U33	U12	U13	U23
O1	0.0309 (8)	0.0572 (11)	0.0589 (10)	−0.0073 (7)	−0.0071 (7)	−0.0018 (8)
O2	0.0468 (9)	0.0525 (10)	0.0488 (9)	0.0202 (8)	0.0092 (7)	−0.0012 (8)
O3	0.0354 (9)	0.0933 (15)	0.0558 (11)	0.0041 (9)	0.0070 (8)	0.0310 (10)
N1	0.0323 (8)	0.0317 (9)	0.0329 (9)	−0.0016 (7)	−0.0043 (7)	−0.0033 (7)
N2	0.0353 (9)	0.0258 (8)	0.0341 (9)	0.0033 (7)	−0.0004 (7)	−0.0021 (7)
N3	0.0358 (10)	0.0837 (17)	0.0502 (12)	0.0095 (10)	0.0098 (9)	0.0248 (12)
C1	0.0240 (9)	0.0394 (11)	0.0355 (10)	0.0023 (8)	0.0023 (8)	0.0057 (9)
C2	0.0301 (10)	0.0288 (10)	0.0433 (11)	0.0006 (8)	−0.0030 (8)	0.0018 (9)
C3	0.0294 (9)	0.0271 (9)	0.0254 (9)	−0.0012 (7)	0.0005 (7)	0.0043 (7)
C4	0.0411 (11)	0.0323 (10)	0.0311 (10)	0.0037 (9)	0.0073 (8)	0.0007 (8)
C5	0.0343 (10)	0.0454 (13)	0.0381 (11)	0.0097 (9)	0.0108 (8)	0.0105 (10)
C6	0.0268 (9)	0.0501 (13)	0.0378 (11)	−0.0031 (9)	0.0016 (8)	0.0137 (10)
C7	0.0334 (10)	0.0360 (11)	0.0309 (10)	−0.0064 (8)	−0.0022 (8)	0.0032 (8)
C8	0.0282 (9)	0.0262 (9)	0.0261 (9)	0.0003 (7)	0.0021 (7)	0.0046 (7)
C9	0.0316 (10)	0.0406 (11)	0.0279 (10)	0.0093 (9)	−0.0007 (8)	−0.0003 (8)
C10	0.0476 (13)	0.0508 (14)	0.0381 (12)	0.0017 (11)	−0.0096 (10)	−0.0118 (10)
C11	0.0525 (14)	0.0262 (11)	0.0638 (15)	0.0033 (10)	−0.0079 (12)	−0.0012 (10)
C12	0.0295 (10)	0.0477 (13)	0.0416 (12)	−0.0011 (9)	0.0047 (9)	0.0052 (10)
C13	0.0413 (12)	0.0481 (13)	0.0417 (12)	0.0002 (10)	0.0078 (10)	0.0031 (10)
C14	0.0461 (13)	0.0521 (14)	0.0388 (12)	0.0057 (11)	0.0102 (10)	0.0026 (11)
C15	0.0359 (11)	0.0525 (14)	0.0317 (10)	0.0034 (10)	0.0014 (8)	0.0006 (10)
C16	0.0353 (10)	0.0452 (12)	0.0263 (9)	0.0037 (9)	0.0004 (8)	−0.0029 (9)
C17	0.0331 (10)	0.0492 (13)	0.0426 (12)	0.0057 (10)	0.0037 (9)	−0.0041 (10)
C18	0.0430 (12)	0.0409 (13)	0.0513 (14)	0.0042 (10)	−0.0086 (10)	0.0000 (11)
C19	0.0430 (12)	0.0484 (13)	0.0404 (12)	−0.0126 (10)	−0.0015 (9)	0.0013 (10)
C20	0.0296 (10)	0.0586 (14)	0.0371 (11)	−0.0018 (10)	0.0037 (8)	−0.0073 (10)
C21	0.0347 (10)	0.0458 (12)	0.0322 (10)	0.0068 (9)	−0.0001 (8)	−0.0033 (9)

O1—C2	1.225 (2)	C10—H10B	0.9600
O2—C9	1.220 (2)	C10—H10C	0.9600
O3—N3	1.407 (3)	C11—H11A	0.9600
O3—C13	1.469 (3)	C11—H11B	0.9600
N1—C2	1.360 (3)	C11—H11C	0.9600
N1—C3	1.424 (2)	C12—C13	1.506 (3)
N1—C10	1.474 (3)	C12—H12A	0.9700
N2—C9	1.364 (3)	C12—H12B	0.9700
N2—C8	1.420 (2)	C13—C14	1.527 (3)
N2—C11	1.467 (3)	C13—H13	0.9800
N3—C15	1.287 (3)	C14—C15	1.502 (3)
C1—C12	1.520 (3)	C14—H14A	0.9700
C1—C2	1.522 (3)	C14—H14B	0.9700
C1—C9	1.527 (3)	C15—C16	1.472 (3)
C1—H1	0.9800	C16—C21	1.391 (3)
C3—C4	1.396 (3)	C16—C17	1.398 (3)
C3—C8	1.400 (3)	C17—C18	1.378 (3)
C4—C5	1.383 (3)	C17—H17	0.9300
C4—H4	0.9300	C18—C19	1.388 (3)
C5—C6	1.378 (3)	C18—H18	0.9300
C5—H5	0.9300	C19—C20	1.377 (3)
C6—C7	1.381 (3)	C19—H19	0.9300
C6—H6	0.9300	C20—C21	1.383 (3)
C7—C8	1.397 (3)	C20—H20	0.9300
C7—H7	0.9300	C21—H21	0.9300
C10—H10A	0.9600
N3—O3—C13	109.19 (16)	N2—C11—H11B	109.5
C2—N1—C3	122.92 (17)	H11A—C11—H11B	109.5
C2—N1—C10	117.75 (17)	N2—C11—H11C	109.5
C3—N1—C10	119.14 (17)	H11A—C11—H11C	109.5
C9—N2—C8	122.31 (17)	H11B—C11—H11C	109.5
C9—N2—C11	118.38 (18)	C13—C12—C1	111.85 (18)
C8—N2—C11	119.31 (18)	C13—C12—H12A	109.2
C15—N3—O3	109.9 (2)	C1—C12—H12A	109.2
C12—C1—C2	112.76 (17)	C13—C12—H12B	109.2
C12—C1—C9	112.80 (18)	C1—C12—H12B	109.2
C2—C1—C9	104.18 (16)	H12A—C12—H12B	107.9
C12—C1—H1	109.0	O3—C13—C12	108.00 (19)
C2—C1—H1	109.0	O3—C13—C14	104.44 (19)
C9—C1—H1	109.0	C12—C13—C14	113.5 (2)
O1—C2—N1	122.1 (2)	O3—C13—H13	110.2
O1—C2—C1	122.36 (19)	C12—C13—H13	110.2
N1—C2—C1	115.42 (17)	C14—C13—H13	110.2
C4—C3—C8	118.96 (18)	C15—C14—C13	101.25 (18)
C4—C3—N1	119.68 (18)	C15—C14—H14A	111.5
C8—C3—N1	121.35 (17)	C13—C14—H14A	111.5
C5—C4—C3	120.9 (2)	C15—C14—H14B	111.5
C5—C4—H4	119.6	C13—C14—H14B	111.5
C3—C4—H4	119.6	H14A—C14—H14B	109.3
C6—C5—C4	119.9 (2)	N3—C15—C16	121.3 (2)
C6—C5—H5	120.0	N3—C15—C14	113.6 (2)
C4—C5—H5	120.0	C16—C15—C14	125.12 (19)
C5—C6—C7	120.13 (19)	C21—C16—C17	118.5 (2)
C5—C6—H6	119.9	C21—C16—C15	121.3 (2)
C7—C6—H6	119.9	C17—C16—C15	120.20 (19)
C6—C7—C8	120.6 (2)	C18—C17—C16	120.2 (2)
C6—C7—H7	119.7	C18—C17—H17	119.9
C8—C7—H7	119.7	C16—C17—H17	119.9
C7—C8—C3	119.40 (18)	C17—C18—C19	120.6 (2)
C7—C8—N2	119.25 (18)	C17—C18—H18	119.7
C3—C8—N2	121.35 (17)	C19—C18—H18	119.7
O2—C9—N2	122.0 (2)	C20—C19—C18	119.7 (2)
O2—C9—C1	122.5 (2)	C20—C19—H19	120.1
N2—C9—C1	115.40 (17)	C18—C19—H19	120.1
N1—C10—H10A	109.5	C19—C20—C21	120.0 (2)
N1—C10—H10B	109.5	C19—C20—H20	120.0
H10A—C10—H10B	109.5	C21—C20—H20	120.0
N1—C10—H10C	109.5	C20—C21—C16	121.0 (2)
H10A—C10—H10C	109.5	C20—C21—H21	119.5
H10B—C10—H10C	109.5	C16—C21—H21	119.5
N2—C11—H11A	109.5