1-[2-(2-Oxo-1,3-oxazolidin-3-yl)eth-yl]-4-phenyl-1H-1,5-benzodiazepin-2(3H)-one.

The seven-membered ring in the title compound, C(20)H(19)N(3)O(3), adopts a boat conformation with the two phenyl-ene C atoms representing the stern and the methyl-ene C atom the prow. The dihedral angle between the best plane through the seven-membered ring (r.m.s deviation = 0.358 Å) and the phenyl substituent is 55.8 (1)°. The two rings at either ends of the ethyl chain are staggered [N-CH(2)-CH(2)-N torsion angle = 57.5 (4)°].

Related literature

For the background to 2,3-dihydro-1H-1,5-benzodiazepin-2-ones, see: Ahabchane et al. (1999 ▶). For a related structure, see: Ballo et al. (2010 ▶).

Experimental

Crystal data

C20H19N3O3

M = 349.38

Orthorhombic,

a = 9.0163 (5) Å

b = 11.6671 (6) Å

c = 16.2019 (8) Å

V = 1704.34 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.25 × 0.25 × 0.15 mm

Data collection

Bruker X8 APEXII diffractometer

9253 measured reflections

2053 independent reflections

1578 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.102

S = 0.90

2053 reflections

235 parameters

H-atom parameters constrained

Δρmax = 0.12 e Å−3

Δρmin = −0.16 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/S160053681002828X/zs2052sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681002828X/zs2052Isup2.hkl

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

C20H19N3O3	F(000) = 736
Mr = 349.38	Dx = 1.362 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2227 reflections
a = 9.0163 (5) Å	θ = 2.9–21.0°
b = 11.6671 (6) Å	µ = 0.09 mm−1
c = 16.2019 (8) Å	T = 293 K
V = 1704.34 (15) Å3	Prism, colorless
Z = 4	0.25 × 0.25 × 0.15 mm

Bruker X8 APEXII diffractometer	1578 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.039
graphite	θmax = 26.7°, θmin = 2.9°
φ and ω scans	h = −11→10
9253 measured reflections	k = −14→13
2053 independent reflections	l = −20→14

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102	H-atom parameters constrained
S = 0.90	w = 1/[σ2(Fo2) + (0.0742P)2] where P = (Fo2 + 2Fc2)/3
2053 reflections	(Δ/σ)max = 0.001
235 parameters	Δρmax = 0.12 e Å−3
0 restraints	Δρmin = −0.16 e Å−3

	x	y	z	Uiso*/Ueq
N1	0.3905 (2)	0.62919 (16)	0.33575 (12)	0.0439 (5)
N2	0.1611 (2)	0.45822 (16)	0.37488 (12)	0.0416 (5)
N3	0.4287 (2)	0.61202 (17)	0.51545 (12)	0.0458 (5)
O1	0.5951 (2)	0.51620 (17)	0.32572 (12)	0.0669 (5)
O2	0.1947 (2)	0.60716 (17)	0.57036 (13)	0.0677 (6)
O3	0.3700 (2)	0.48444 (16)	0.61065 (11)	0.0629 (5)
C1	0.2372 (3)	0.6471 (2)	0.31906 (14)	0.0434 (5)
C2	0.1935 (3)	0.7508 (2)	0.28491 (17)	0.0597 (7)
H2	0.2650	0.8049	0.2710	0.072*
C3	0.0461 (4)	0.7750 (2)	0.27117 (19)	0.0697 (8)
H3	0.0181	0.8445	0.2477	0.084*
C4	−0.0596 (3)	0.6950 (3)	0.29269 (17)	0.0646 (8)
H4	−0.1594	0.7110	0.2841	0.078*
C5	−0.0192 (3)	0.5927 (2)	0.32647 (15)	0.0520 (6)
H5	−0.0921	0.5403	0.3414	0.062*
C6	0.1301 (3)	0.5651 (2)	0.33911 (13)	0.0416 (5)
C7	0.2709 (3)	0.39924 (19)	0.34851 (13)	0.0405 (5)
C8	0.3658 (3)	0.4400 (2)	0.27737 (14)	0.0477 (6)
H8A	0.4248	0.3775	0.2554	0.057*
H8B	0.3046	0.4710	0.2335	0.057*
C9	0.4635 (3)	0.5312 (2)	0.31346 (14)	0.0467 (6)
C10	0.4696 (3)	0.7153 (2)	0.38443 (15)	0.0516 (6)
H10A	0.4560	0.7899	0.3592	0.062*
H10B	0.5748	0.6979	0.3839	0.062*
C11	0.4161 (3)	0.7200 (2)	0.47313 (15)	0.0483 (6)
H11A	0.4732	0.7772	0.5027	0.058*
H11B	0.3131	0.7440	0.4737	0.058*
C12	0.3193 (3)	0.5726 (2)	0.56469 (15)	0.0480 (6)
C13	0.5683 (3)	0.5585 (3)	0.53446 (17)	0.0590 (7)
H13A	0.6327	0.6096	0.5652	0.071*
H13B	0.6190	0.5333	0.4849	0.071*
C14	0.5192 (4)	0.4584 (3)	0.58632 (19)	0.0697 (8)
H14A	0.5224	0.3879	0.5546	0.084*
H14B	0.5826	0.4500	0.6343	0.084*
C15	0.3119 (3)	0.29286 (18)	0.39276 (14)	0.0415 (5)
C16	0.2634 (3)	0.2771 (2)	0.47373 (17)	0.0542 (6)
H16	0.2040	0.3321	0.4989	0.065*
C17	0.3038 (4)	0.1793 (3)	0.51664 (19)	0.0674 (8)
H17	0.2710	0.1690	0.5706	0.081*
C18	0.3914 (3)	0.0977 (3)	0.4807 (2)	0.0658 (8)
H18	0.4195	0.0331	0.5104	0.079*
C19	0.4373 (4)	0.1114 (3)	0.4010 (2)	0.0701 (8)
H19	0.4946	0.0551	0.3759	0.084*
C20	0.3988 (3)	0.2088 (2)	0.35785 (18)	0.0604 (7)
H20	0.4323	0.2180	0.3040	0.072*

	U11	U22	U33	U12	U13	U23
N1	0.0423 (11)	0.0491 (11)	0.0402 (10)	−0.0064 (9)	−0.0003 (9)	0.0029 (9)
N2	0.0395 (11)	0.0438 (10)	0.0415 (10)	−0.0009 (9)	−0.0001 (8)	−0.0040 (9)
N3	0.0414 (11)	0.0531 (11)	0.0428 (11)	0.0005 (9)	0.0037 (9)	0.0065 (9)
O1	0.0407 (10)	0.0837 (13)	0.0761 (13)	0.0036 (10)	0.0055 (9)	0.0061 (12)
O2	0.0511 (11)	0.0706 (12)	0.0815 (13)	0.0082 (11)	0.0214 (10)	0.0049 (10)
O3	0.0706 (12)	0.0607 (11)	0.0575 (11)	0.0065 (10)	0.0181 (10)	0.0150 (9)
C1	0.0470 (13)	0.0482 (13)	0.0351 (12)	0.0017 (11)	−0.0029 (11)	−0.0027 (11)
C2	0.0711 (18)	0.0510 (14)	0.0570 (16)	0.0016 (14)	−0.0068 (15)	0.0076 (12)
C3	0.080 (2)	0.0593 (16)	0.0695 (19)	0.0250 (16)	−0.0144 (17)	0.0092 (15)
C4	0.0580 (17)	0.0736 (18)	0.0623 (17)	0.0226 (16)	−0.0112 (15)	−0.0051 (15)
C5	0.0434 (13)	0.0644 (16)	0.0483 (14)	0.0065 (12)	−0.0018 (11)	−0.0093 (13)
C6	0.0447 (12)	0.0465 (13)	0.0335 (11)	0.0032 (10)	−0.0008 (10)	−0.0061 (10)
C7	0.0412 (13)	0.0444 (11)	0.0358 (11)	−0.0024 (10)	−0.0031 (10)	−0.0058 (10)
C8	0.0558 (14)	0.0542 (13)	0.0330 (11)	0.0057 (12)	0.0038 (11)	−0.0049 (11)
C9	0.0436 (14)	0.0599 (14)	0.0367 (12)	0.0005 (12)	0.0069 (11)	0.0080 (11)
C10	0.0551 (14)	0.0547 (13)	0.0451 (13)	−0.0174 (12)	−0.0012 (12)	0.0062 (11)
C11	0.0559 (15)	0.0455 (13)	0.0435 (13)	−0.0049 (11)	0.0009 (12)	0.0003 (10)
C12	0.0544 (15)	0.0460 (13)	0.0434 (13)	0.0008 (12)	0.0077 (11)	−0.0045 (11)
C13	0.0464 (14)	0.0794 (19)	0.0513 (15)	0.0070 (13)	0.0019 (12)	0.0094 (14)
C14	0.0655 (18)	0.0788 (19)	0.0650 (17)	0.0178 (16)	0.0061 (15)	0.0164 (16)
C15	0.0388 (11)	0.0417 (11)	0.0440 (13)	−0.0032 (10)	−0.0055 (10)	−0.0049 (10)
C16	0.0557 (15)	0.0557 (14)	0.0512 (15)	−0.0024 (12)	−0.0012 (13)	0.0025 (13)
C17	0.0756 (19)	0.0734 (18)	0.0532 (16)	−0.0086 (17)	−0.0077 (15)	0.0144 (15)
C18	0.0613 (17)	0.0592 (17)	0.077 (2)	0.0008 (14)	−0.0237 (16)	0.0153 (15)
C19	0.074 (2)	0.0600 (17)	0.077 (2)	0.0218 (15)	−0.0054 (17)	−0.0025 (15)
C20	0.0643 (18)	0.0614 (16)	0.0554 (16)	0.0138 (14)	−0.0014 (14)	−0.0048 (13)

N1—C9	1.367 (3)	C8—C9	1.501 (3)
N1—C1	1.424 (3)	C8—H8A	0.9700
N1—C10	1.463 (3)	C8—H8B	0.9700
N2—C7	1.280 (3)	C10—C11	1.517 (4)
N2—C6	1.403 (3)	C10—H10A	0.9700
N3—C12	1.350 (3)	C10—H10B	0.9700
N3—C11	1.439 (3)	C11—H11A	0.9700
N3—C13	1.439 (3)	C11—H11B	0.9700
O1—C9	1.216 (3)	C13—C14	1.505 (4)
O2—C12	1.197 (3)	C13—H13A	0.9700
O3—C12	1.350 (3)	C13—H13B	0.9700
O3—C14	1.435 (4)	C14—H14A	0.9700
C1—C2	1.387 (3)	C14—H14B	0.9700
C1—C6	1.398 (3)	C15—C20	1.377 (3)
C2—C3	1.377 (4)	C15—C16	1.395 (4)
C2—H2	0.9300	C16—C17	1.385 (4)
C3—C4	1.378 (4)	C16—H16	0.9300
C3—H3	0.9300	C17—C18	1.367 (4)
C4—C5	1.363 (4)	C17—H17	0.9300
C4—H4	0.9300	C18—C19	1.364 (5)
C5—C6	1.399 (3)	C18—H18	0.9300
C5—H5	0.9300	C19—C20	1.379 (4)
C7—C15	1.480 (3)	C19—H19	0.9300
C7—C8	1.512 (3)	C20—H20	0.9300
C9—N1—C1	122.7 (2)	C11—C10—H10B	109.1
C9—N1—C10	118.8 (2)	H10A—C10—H10B	107.9
C1—N1—C10	118.3 (2)	N3—C11—C10	113.2 (2)
C7—N2—C6	119.6 (2)	N3—C11—H11A	108.9
C12—N3—C11	121.5 (2)	C10—C11—H11A	108.9
C12—N3—C13	111.40 (19)	N3—C11—H11B	108.9
C11—N3—C13	123.5 (2)	C10—C11—H11B	108.9
C12—O3—C14	109.1 (2)	H11A—C11—H11B	107.7
C2—C1—C6	119.6 (2)	O2—C12—O3	122.2 (2)
C2—C1—N1	118.7 (2)	O2—C12—N3	128.1 (2)
C6—C1—N1	121.7 (2)	O3—C12—N3	109.8 (2)
C3—C2—C1	121.2 (3)	N3—C13—C14	101.5 (2)
C3—C2—H2	119.4	N3—C13—H13A	111.5
C1—C2—H2	119.4	C14—C13—H13A	111.5
C2—C3—C4	119.1 (3)	N3—C13—H13B	111.5
C2—C3—H3	120.4	C14—C13—H13B	111.5
C4—C3—H3	120.4	H13A—C13—H13B	109.3
C5—C4—C3	120.7 (3)	O3—C14—C13	105.4 (2)
C5—C4—H4	119.7	O3—C14—H14A	110.7
C3—C4—H4	119.7	C13—C14—H14A	110.7
C4—C5—C6	121.1 (3)	O3—C14—H14B	110.7
C4—C5—H5	119.4	C13—C14—H14B	110.7
C6—C5—H5	119.4	H14A—C14—H14B	108.8
C1—C6—C5	118.3 (2)	C20—C15—C16	118.1 (2)
C1—C6—N2	124.5 (2)	C20—C15—C7	122.7 (2)
C5—C6—N2	117.2 (2)	C16—C15—C7	119.2 (2)
N2—C7—C15	118.8 (2)	C17—C16—C15	119.9 (3)
N2—C7—C8	121.6 (2)	C17—C16—H16	120.0
C15—C7—C8	119.5 (2)	C15—C16—H16	120.0
C9—C8—C7	104.95 (17)	C18—C17—C16	120.7 (3)
C9—C8—H8A	110.8	C18—C17—H17	119.6
C7—C8—H8A	110.8	C16—C17—H17	119.6
C9—C8—H8B	110.8	C19—C18—C17	119.8 (3)
C7—C8—H8B	110.8	C19—C18—H18	120.1
H8A—C8—H8B	108.8	C17—C18—H18	120.1
O1—C9—N1	123.2 (2)	C18—C19—C20	120.0 (3)
O1—C9—C8	122.3 (2)	C18—C19—H19	120.0
N1—C9—C8	114.4 (2)	C20—C19—H19	120.0
N1—C10—C11	112.4 (2)	C15—C20—C19	121.4 (3)
N1—C10—H10A	109.1	C15—C20—H20	119.3
C11—C10—H10A	109.1	C19—C20—H20	119.3
N1—C10—H10B	109.1
C9—N1—C1—C2	−132.7 (2)	C9—N1—C10—C11	−108.0 (2)
C10—N1—C1—C2	52.3 (3)	C1—N1—C10—C11	67.3 (3)
C9—N1—C1—C6	49.8 (3)	C12—N3—C11—C10	−137.1 (2)
C10—N1—C1—C6	−125.2 (2)	C13—N3—C11—C10	66.2 (3)
C6—C1—C2—C3	0.7 (4)	N1—C10—C11—N3	57.5 (3)
N1—C1—C2—C3	−176.8 (3)	C14—O3—C12—O2	176.3 (3)
C1—C2—C3—C4	0.7 (5)	C14—O3—C12—N3	−4.3 (3)
C2—C3—C4—C5	−0.6 (4)	C11—N3—C12—O2	12.8 (4)
C3—C4—C5—C6	−1.0 (4)	C13—N3—C12—O2	172.0 (3)
C2—C1—C6—C5	−2.2 (3)	C11—N3—C12—O3	−166.5 (2)
N1—C1—C6—C5	175.2 (2)	C13—N3—C12—O3	−7.3 (3)
C2—C1—C6—N2	−179.1 (2)	C12—N3—C13—C14	14.8 (3)
N1—C1—C6—N2	−1.6 (3)	C11—N3—C13—C14	173.5 (2)
C4—C5—C6—C1	2.4 (4)	C12—O3—C14—C13	13.4 (3)
C4—C5—C6—N2	179.5 (2)	N3—C13—C14—O3	−16.4 (3)
C7—N2—C6—C1	−42.9 (3)	N2—C7—C15—C20	161.8 (2)
C7—N2—C6—C5	140.2 (2)	C8—C7—C15—C20	−22.5 (3)
C6—N2—C7—C15	173.44 (19)	N2—C7—C15—C16	−19.4 (3)
C6—N2—C7—C8	−2.2 (3)	C8—C7—C15—C16	156.3 (2)
N2—C7—C8—C9	76.5 (3)	C20—C15—C16—C17	0.4 (4)
C15—C7—C8—C9	−99.1 (2)	C7—C15—C16—C17	−178.4 (2)
C1—N1—C9—O1	178.2 (2)	C15—C16—C17—C18	0.2 (4)
C10—N1—C9—O1	−6.8 (3)	C16—C17—C18—C19	−1.3 (4)
C1—N1—C9—C8	−5.5 (3)	C17—C18—C19—C20	1.8 (5)
C10—N1—C9—C8	169.45 (19)	C16—C15—C20—C19	0.1 (4)
C7—C8—C9—O1	107.4 (3)	C7—C15—C20—C19	178.9 (3)
C7—C8—C9—N1	−68.8 (2)	C18—C19—C20—C15	−1.2 (5)