3-{[3-(4-Chloro-phen-yl)-4,5-dihydro-1,2-oxazol-5-yl]meth-yl}-1,5-dimethyl-1H-1,5-benzodiazepine-2,4(3H,5H)-dione.

The seven-membered ring of the title mol-ecule, C(21)H(20)ClN(3)O(3), 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 substituent at the 3-position occupies an equatorial position; its five-membered ring is approximately planar (r.m.s. deviation = 0.081 Å), and is aligned at 14.5 (1)° with respect to the chloro-phenyl ring to which it is connected.

Related literature

For the crystal structure of the tetra­decyl-substituted analog, see: Dardouri et al. (2011 ▶).

Experimental

Crystal data

C21H20ClN3O3

M = 397.85

Triclinic,

a = 8.1821 (1) Å

b = 9.0741 (1) Å

c = 13.3792 (2) Å

α = 79.748 (1)°

β = 80.142 (1)°

γ = 85.910 (1)°

V = 962.19 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.23 mm−1

T = 295 K

0.40 × 0.30 × 0.20 mm

Data collection

Bruker X8 APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.915, T max = 0.956

19243 measured reflections

4383 independent reflections

4056 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.066

wR(F 2) = 0.184

S = 1.03

4383 reflections

256 parameters

H-atom parameters constrained

Δρmax = 0.83 e Å−3

Δρmin = −0.44 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); 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 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681100657X/bt5479sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681100657X/bt5479Isup2.hkl

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

C21H20ClN3O3	Z = 2
Mr = 397.85	F(000) = 416
Triclinic, P1	Dx = 1.373 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.1821 (1) Å	Cell parameters from 9887 reflections
b = 9.0741 (1) Å	θ = 3.0–30.7°
c = 13.3792 (2) Å	µ = 0.23 mm−1
α = 79.748 (1)°	T = 295 K
β = 80.142 (1)°	Block, colorless
γ = 85.910 (1)°	0.40 × 0.30 × 0.20 mm
V = 962.19 (2) Å3

Bruker X8 APEXII diffractometer	4383 independent reflections
Radiation source: fine-focus sealed tube	4056 reflections with I > 2σ(I)
graphite	Rint = 0.020
φ and ω scans	θmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
Tmin = 0.915, Tmax = 0.956	k = −11→11
19243 measured reflections	l = −17→17

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)] = 0.066	H-atom parameters constrained
wR(F2) = 0.184	w = 1/[σ2(Fo2) + (0.1062P)2 + 0.889P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.001
4383 reflections	Δρmax = 0.83 e Å−3
256 parameters	Δρmin = −0.44 e Å−3
0 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: 0.046 (8)

	x	y	z	Uiso*/Ueq
Cl1	0.00333 (8)	0.14321 (7)	1.07254 (5)	0.0471 (2)
O1	0.2880 (2)	1.2329 (2)	0.66476 (13)	0.0428 (4)
O2	0.6469 (2)	1.2468 (2)	0.82002 (12)	0.0430 (4)
O3	0.6108 (2)	0.79540 (18)	0.76659 (12)	0.0400 (4)
N1	0.5122 (2)	1.2697 (2)	0.53908 (14)	0.0337 (4)
N2	0.7763 (2)	1.2907 (2)	0.65440 (13)	0.0310 (4)
N3	0.5112 (2)	0.6671 (2)	0.78978 (14)	0.0353 (4)
C1	0.6816 (3)	1.2379 (2)	0.50002 (15)	0.0309 (4)
C2	0.7216 (3)	1.2001 (3)	0.40171 (18)	0.0452 (6)
H2	0.6374	1.1910	0.3647	0.054*
C3	0.8856 (4)	1.1760 (4)	0.35894 (19)	0.0504 (7)
H3	0.9109	1.1522	0.2931	0.060*
C4	1.0116 (3)	1.1870 (3)	0.4132 (2)	0.0448 (6)
H4	1.1216	1.1710	0.3839	0.054*
C5	0.9744 (3)	1.2219 (3)	0.51136 (18)	0.0360 (5)
H5	1.0596	1.2275	0.5483	0.043*
C6	0.8100 (3)	1.2487 (2)	0.55536 (15)	0.0284 (4)
C7	0.4069 (3)	1.3563 (3)	0.46807 (19)	0.0449 (6)
H7A	0.3220	1.4127	0.5059	0.067*
H7B	0.3563	1.2889	0.4359	0.067*
H7C	0.4739	1.4237	0.4163	0.067*
C8	0.4365 (3)	1.2097 (2)	0.63486 (16)	0.0313 (4)
C9	0.5486 (3)	1.1145 (2)	0.70220 (15)	0.0293 (4)
H9	0.6178	1.0465	0.6616	0.035*
C10	0.6618 (3)	1.2213 (2)	0.73248 (15)	0.0301 (4)
C11	0.8826 (3)	1.3976 (3)	0.6799 (2)	0.0437 (6)
H11A	0.8160	1.4626	0.7216	0.065*
H11B	0.9365	1.4563	0.6177	0.065*
H11C	0.9648	1.3438	0.7173	0.065*
C12	0.4489 (3)	1.0212 (2)	0.79575 (16)	0.0307 (4)
H12A	0.4059	1.0846	0.8463	0.037*
H12B	0.3551	0.9814	0.7752	0.037*
C13	0.5550 (3)	0.8928 (2)	0.84372 (16)	0.0326 (4)
H13	0.6499	0.9304	0.8659	0.039*
C14	0.4547 (3)	0.7892 (2)	0.93283 (15)	0.0317 (4)
H14A	0.5181	0.7544	0.9881	0.038*
H14B	0.3515	0.8382	0.9599	0.038*
C15	0.4243 (3)	0.6634 (2)	0.87944 (15)	0.0301 (4)
C16	0.3142 (2)	0.5391 (2)	0.92464 (15)	0.0290 (4)
C17	0.2745 (3)	0.4381 (3)	0.86525 (16)	0.0352 (5)
H17	0.3144	0.4520	0.7950	0.042*
C18	0.1772 (3)	0.3186 (3)	0.90967 (18)	0.0367 (5)
H18	0.1508	0.2523	0.8698	0.044*
C19	0.1190 (3)	0.2982 (2)	1.01501 (17)	0.0330 (4)
C20	0.1526 (3)	0.3979 (2)	1.07529 (16)	0.0310 (4)
H20	0.1109	0.3840	1.1453	0.037*
C21	0.2496 (3)	0.5188 (2)	1.02965 (15)	0.0291 (4)
H21	0.2718	0.5871	1.0693	0.035*

	U11	U22	U33	U12	U13	U23
Cl1	0.0506 (4)	0.0392 (3)	0.0554 (4)	−0.0106 (2)	−0.0094 (3)	−0.0145 (3)
O1	0.0328 (8)	0.0558 (11)	0.0374 (9)	0.0037 (7)	−0.0019 (6)	−0.0071 (7)
O2	0.0561 (10)	0.0510 (10)	0.0238 (7)	−0.0044 (8)	−0.0058 (7)	−0.0114 (7)
O3	0.0490 (9)	0.0360 (8)	0.0274 (7)	0.0054 (7)	0.0083 (6)	−0.0011 (6)
N1	0.0331 (9)	0.0421 (10)	0.0258 (8)	−0.0033 (7)	−0.0058 (7)	−0.0037 (7)
N2	0.0381 (9)	0.0322 (9)	0.0248 (8)	−0.0041 (7)	−0.0079 (7)	−0.0063 (7)
N3	0.0432 (10)	0.0348 (9)	0.0241 (8)	0.0085 (8)	−0.0014 (7)	−0.0026 (7)
C1	0.0339 (10)	0.0360 (10)	0.0220 (9)	−0.0061 (8)	−0.0025 (7)	−0.0030 (7)
C2	0.0481 (13)	0.0640 (16)	0.0256 (10)	−0.0096 (11)	−0.0045 (9)	−0.0121 (10)
C3	0.0542 (15)	0.0698 (18)	0.0267 (11)	−0.0104 (13)	0.0074 (10)	−0.0166 (11)
C4	0.0384 (12)	0.0523 (14)	0.0400 (12)	−0.0074 (10)	0.0093 (10)	−0.0104 (11)
C5	0.0338 (11)	0.0379 (11)	0.0356 (11)	−0.0038 (8)	−0.0045 (8)	−0.0042 (9)
C6	0.0346 (10)	0.0284 (9)	0.0214 (9)	−0.0045 (7)	−0.0037 (7)	−0.0018 (7)
C7	0.0408 (12)	0.0581 (15)	0.0366 (12)	−0.0014 (11)	−0.0149 (10)	−0.0020 (11)
C8	0.0338 (10)	0.0339 (10)	0.0271 (10)	−0.0031 (8)	−0.0027 (8)	−0.0091 (8)
C9	0.0326 (10)	0.0301 (9)	0.0235 (9)	−0.0002 (7)	−0.0005 (7)	−0.0045 (7)
C10	0.0370 (10)	0.0306 (10)	0.0224 (9)	0.0026 (8)	−0.0059 (7)	−0.0042 (7)
C11	0.0472 (13)	0.0469 (13)	0.0433 (13)	−0.0099 (10)	−0.0154 (10)	−0.0137 (10)
C12	0.0292 (9)	0.0346 (10)	0.0267 (9)	−0.0003 (8)	−0.0023 (7)	−0.0030 (8)
C13	0.0309 (10)	0.0381 (11)	0.0263 (9)	0.0005 (8)	−0.0025 (7)	−0.0016 (8)
C14	0.0391 (11)	0.0322 (10)	0.0211 (9)	−0.0001 (8)	−0.0008 (8)	−0.0015 (7)
C15	0.0358 (10)	0.0327 (10)	0.0202 (8)	0.0085 (8)	−0.0057 (7)	−0.0033 (7)
C16	0.0311 (10)	0.0328 (10)	0.0237 (9)	0.0069 (8)	−0.0067 (7)	−0.0075 (7)
C17	0.0383 (11)	0.0450 (12)	0.0250 (9)	0.0090 (9)	−0.0086 (8)	−0.0145 (8)
C18	0.0383 (11)	0.0415 (12)	0.0374 (11)	0.0085 (9)	−0.0143 (9)	−0.0216 (9)
C19	0.0306 (10)	0.0337 (10)	0.0376 (11)	0.0033 (8)	−0.0095 (8)	−0.0116 (8)
C20	0.0337 (10)	0.0336 (10)	0.0267 (9)	0.0002 (8)	−0.0044 (8)	−0.0094 (8)
C21	0.0349 (10)	0.0304 (10)	0.0231 (9)	0.0029 (8)	−0.0056 (7)	−0.0085 (7)

Cl1—C19	1.738 (2)	C9—C12	1.523 (3)
O1—C8	1.228 (3)	C9—C10	1.536 (3)
O2—C10	1.218 (3)	C9—H9	0.9800
O3—N3	1.427 (3)	C11—H11A	0.9600
O3—C13	1.470 (3)	C11—H11B	0.9600
N1—C8	1.360 (3)	C11—H11C	0.9600
N1—C1	1.423 (3)	C12—C13	1.518 (3)
N1—C7	1.477 (3)	C12—H12A	0.9700
N2—C10	1.371 (3)	C12—H12B	0.9700
N2—C6	1.420 (3)	C13—C14	1.534 (3)
N2—C11	1.467 (3)	C13—H13	0.9800
N3—C15	1.282 (3)	C14—C15	1.506 (3)
C1—C2	1.397 (3)	C14—H14A	0.9700
C1—C6	1.403 (3)	C14—H14B	0.9700
C2—C3	1.384 (4)	C15—C16	1.471 (3)
C2—H2	0.9300	C16—C21	1.398 (3)
C3—C4	1.378 (4)	C16—C17	1.403 (3)
C3—H3	0.9300	C17—C18	1.376 (4)
C4—C5	1.383 (3)	C17—H17	0.9300
C4—H4	0.9300	C18—C19	1.392 (3)
C5—C6	1.396 (3)	C18—H18	0.9300
C5—H5	0.9300	C19—C20	1.384 (3)
C7—H7A	0.9600	C20—C21	1.388 (3)
C7—H7B	0.9600	C20—H20	0.9300
C7—H7C	0.9600	C21—H21	0.9300
C8—C9	1.514 (3)
N3—O3—C13	109.02 (15)	N2—C11—H11B	109.5
C8—N1—C1	123.46 (18)	H11A—C11—H11B	109.5
C8—N1—C7	117.58 (19)	N2—C11—H11C	109.5
C1—N1—C7	118.47 (18)	H11A—C11—H11C	109.5
C10—N2—C6	122.62 (17)	H11B—C11—H11C	109.5
C10—N2—C11	117.51 (18)	C13—C12—C9	111.22 (17)
C6—N2—C11	119.31 (18)	C13—C12—H12A	109.4
C15—N3—O3	109.03 (18)	C9—C12—H12A	109.4
C2—C1—C6	119.0 (2)	C13—C12—H12B	109.4
C2—C1—N1	118.8 (2)	C9—C12—H12B	109.4
C6—C1—N1	122.17 (18)	H12A—C12—H12B	108.0
C3—C2—C1	120.5 (2)	O3—C13—C12	107.78 (17)
C3—C2—H2	119.8	O3—C13—C14	103.57 (17)
C1—C2—H2	119.8	C12—C13—C14	112.48 (17)
C4—C3—C2	120.5 (2)	O3—C13—H13	110.9
C4—C3—H3	119.8	C12—C13—H13	110.9
C2—C3—H3	119.8	C14—C13—H13	110.9
C3—C4—C5	119.9 (2)	C15—C14—C13	100.88 (16)
C3—C4—H4	120.0	C15—C14—H14A	111.6
C5—C4—H4	120.0	C13—C14—H14A	111.6
C4—C5—C6	120.5 (2)	C15—C14—H14B	111.6
C4—C5—H5	119.7	C13—C14—H14B	111.6
C6—C5—H5	119.7	H14A—C14—H14B	109.4
C5—C6—C1	119.58 (19)	N3—C15—C16	120.6 (2)
C5—C6—N2	119.19 (19)	N3—C15—C14	114.1 (2)
C1—C6—N2	121.20 (18)	C16—C15—C14	125.22 (17)
N1—C7—H7A	109.5	C21—C16—C17	118.9 (2)
N1—C7—H7B	109.5	C21—C16—C15	119.55 (19)
H7A—C7—H7B	109.5	C17—C16—C15	121.59 (19)
N1—C7—H7C	109.5	C18—C17—C16	120.8 (2)
H7A—C7—H7C	109.5	C18—C17—H17	119.6
H7B—C7—H7C	109.5	C16—C17—H17	119.6
O1—C8—N1	122.1 (2)	C17—C18—C19	119.1 (2)
O1—C8—C9	122.53 (19)	C17—C18—H18	120.4
N1—C8—C9	115.32 (18)	C19—C18—H18	120.4
C8—C9—C12	111.58 (17)	C20—C19—C18	121.4 (2)
C8—C9—C10	107.09 (17)	C20—C19—Cl1	119.19 (17)
C12—C9—C10	112.23 (17)	C18—C19—Cl1	119.38 (17)
C8—C9—H9	108.6	C21—C20—C19	119.01 (19)
C12—C9—H9	108.6	C21—C20—H20	120.5
C10—C9—H9	108.6	C19—C20—H20	120.5
O2—C10—N2	122.0 (2)	C20—C21—C16	120.69 (19)
O2—C10—C9	121.92 (19)	C20—C21—H21	119.7
N2—C10—C9	116.09 (17)	C16—C21—H21	119.7
N2—C11—H11A	109.5
C13—O3—N3—C15	−11.1 (2)	C11—N2—C10—C9	177.93 (19)
C8—N1—C1—C2	132.2 (2)	C8—C9—C10—O2	109.6 (2)
C7—N1—C1—C2	−39.5 (3)	C12—C9—C10—O2	−13.1 (3)
C8—N1—C1—C6	−50.2 (3)	C8—C9—C10—N2	−68.0 (2)
C7—N1—C1—C6	138.0 (2)	C12—C9—C10—N2	169.27 (17)
C6—C1—C2—C3	−1.0 (4)	C8—C9—C12—C13	162.03 (18)
N1—C1—C2—C3	176.6 (2)	C10—C9—C12—C13	−77.8 (2)
C1—C2—C3—C4	0.9 (4)	N3—O3—C13—C12	−101.45 (18)
C2—C3—C4—C5	0.2 (4)	N3—O3—C13—C14	17.9 (2)
C3—C4—C5—C6	−1.1 (4)	C9—C12—C13—O3	−61.8 (2)
C4—C5—C6—C1	1.0 (3)	C9—C12—C13—C14	−175.36 (17)
C4—C5—C6—N2	−177.2 (2)	O3—C13—C14—C15	−17.1 (2)
C2—C1—C6—C5	0.1 (3)	C12—C13—C14—C15	99.0 (2)
N1—C1—C6—C5	−177.46 (19)	O3—N3—C15—C16	−177.74 (17)
C2—C1—C6—N2	178.3 (2)	O3—N3—C15—C14	−1.2 (2)
N1—C1—C6—N2	0.7 (3)	C13—C14—C15—N3	12.0 (2)
C10—N2—C6—C5	−130.1 (2)	C13—C14—C15—C16	−171.60 (18)
C11—N2—C6—C5	41.1 (3)	N3—C15—C16—C21	165.85 (19)
C10—N2—C6—C1	51.7 (3)	C14—C15—C16—C21	−10.3 (3)
C11—N2—C6—C1	−137.1 (2)	N3—C15—C16—C17	−13.0 (3)
C1—N1—C8—O1	−176.2 (2)	C14—C15—C16—C17	170.9 (2)
C7—N1—C8—O1	−4.3 (3)	C21—C16—C17—C18	−1.7 (3)
C1—N1—C8—C9	4.7 (3)	C15—C16—C17—C18	177.11 (19)
C7—N1—C8—C9	176.56 (19)	C16—C17—C18—C19	−0.4 (3)
O1—C8—C9—C12	15.3 (3)	C17—C18—C19—C20	2.0 (3)
N1—C8—C9—C12	−165.63 (18)	C17—C18—C19—Cl1	−177.34 (16)
O1—C8—C9—C10	−107.9 (2)	C18—C19—C20—C21	−1.4 (3)
N1—C8—C9—C10	71.2 (2)	Cl1—C19—C20—C21	177.92 (15)
C6—N2—C10—O2	171.7 (2)	C19—C20—C21—C16	−0.8 (3)
C11—N2—C10—O2	0.3 (3)	C17—C16—C21—C20	2.3 (3)
C6—N2—C10—C9	−10.7 (3)	C15—C16—C21—C20	−176.55 (18)