Ethyl 2-(2-oxo-4-phenyl-2,3-dihydro-1H-1,5-benzodiazepin-1-yl)acetate.

The seven-membered ring in the title compound, C(19)H(18)N(2)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 = 0.343 Å) and the phenyl substituent is 31.9 (1)°. The dihedral angle between this best plane and the best plane through the eth-oxy-carbonyl-methyl substituent (r.m.s. deviation = 0.058 Å) is 72.2 (1)°.

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

C19H18N2O3

M = 322.35

Monoclinic,

a = 12.5198 (4) Å

b = 11.7911 (3) Å

c = 11.2058 (3) Å

β = 97.843 (2)°

V = 1638.75 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.30 × 0.15 × 0.10 mm

Data collection

Bruker X8 APEXII diffractometer

13943 measured reflections

3029 independent reflections

2195 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.114

S = 1.00

3029 reflections

217 parameters

H-atom parameters constrained

Δρmax = 0.12 e Å−3

Δρmin = −0.15 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/S1600536810028278/zs2051sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810028278/zs2051Isup2.hkl

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

C19H18N2O3	F(000) = 680
Mr = 322.35	Dx = 1.307 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3291 reflections
a = 12.5198 (4) Å	θ = 2.4–23.1°
b = 11.7911 (3) Å	µ = 0.09 mm−1
c = 11.2058 (3) Å	T = 293 K
β = 97.843 (2)°	Prism, yellow
V = 1638.75 (8) Å3	0.30 × 0.15 × 0.10 mm
Z = 4

Bruker X8 APEXII diffractometer	2195 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.033
graphite	θmax = 25.5°, θmin = 2.5°
φ and ω scans	h = −15→15
13943 measured reflections	k = −14→14
3029 independent reflections	l = −13→13

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0707P)2] where P = (Fo2 + 2Fc2)/3
3029 reflections	(Δ/σ)max = 0.001
217 parameters	Δρmax = 0.12 e Å−3
0 restraints	Δρmin = −0.15 e Å−3

	x	y	z	Uiso*/Ueq
O1	0.45383 (9)	0.67927 (10)	0.34251 (11)	0.0662 (4)
O2	0.43414 (9)	0.64804 (9)	0.06491 (11)	0.0604 (3)
O3	0.60915 (8)	0.69533 (8)	0.08966 (10)	0.0488 (3)
N1	0.39095 (10)	0.82128 (10)	0.21765 (12)	0.0460 (3)
N2	0.16060 (9)	0.76218 (10)	0.14862 (11)	0.0438 (3)
C1	0.15443 (12)	0.57820 (13)	0.23365 (13)	0.0452 (4)
C2	0.21662 (14)	0.49224 (14)	0.29222 (16)	0.0599 (5)
H2	0.2822	0.5097	0.3381	0.072*
C3	0.18218 (17)	0.38119 (15)	0.28306 (18)	0.0690 (5)
H3	0.2253	0.3242	0.3214	0.083*
C4	0.08518 (16)	0.35429 (14)	0.21804 (18)	0.0648 (5)
H4	0.0618	0.2793	0.2132	0.078*
C5	0.02215 (14)	0.43823 (15)	0.15974 (18)	0.0631 (5)
H5	−0.0440	0.4202	0.1156	0.076*
C6	0.05711 (13)	0.54944 (13)	0.16671 (15)	0.0525 (4)
H6	0.0147	0.6057	0.1259	0.063*
C7	0.19264 (11)	0.69709 (12)	0.23782 (13)	0.0423 (4)
C8	0.27085 (12)	0.73756 (13)	0.34441 (13)	0.0483 (4)
H8A	0.2497	0.8118	0.3702	0.058*
H8B	0.2715	0.6853	0.4113	0.058*
C9	0.38018 (12)	0.74323 (13)	0.30496 (14)	0.0478 (4)
C10	0.49294 (13)	0.81974 (13)	0.16772 (16)	0.0536 (4)
H10A	0.5523	0.8288	0.2323	0.064*
H10B	0.4948	0.8828	0.1124	0.064*
C11	0.50622 (12)	0.71043 (12)	0.10251 (13)	0.0431 (4)
C12	0.63354 (14)	0.59312 (14)	0.02606 (16)	0.0592 (5)
H12A	0.6050	0.5992	−0.0586	0.071*
H12B	0.6010	0.5277	0.0593	0.071*
C13	0.75293 (14)	0.58019 (15)	0.04048 (16)	0.0669 (5)
H13A	0.7712	0.5132	−0.0011	0.100*
H13B	0.7803	0.5736	0.1245	0.100*
H13C	0.7843	0.6453	0.0074	0.100*
C14	0.31063 (11)	0.90246 (12)	0.17520 (12)	0.0414 (4)
C15	0.34293 (13)	1.01399 (12)	0.15912 (14)	0.0511 (4)
H15	0.4153	1.0333	0.1776	0.061*
C16	0.26962 (15)	1.09539 (14)	0.11653 (16)	0.0595 (5)
H16	0.2924	1.1694	0.1066	0.071*
C17	0.16234 (15)	1.06815 (14)	0.08833 (15)	0.0596 (5)
H17	0.1125	1.1238	0.0604	0.072*
C18	0.12908 (13)	0.95835 (13)	0.10160 (14)	0.0528 (4)
H18	0.0566	0.9402	0.0810	0.063*
C19	0.20182 (12)	0.87328 (12)	0.14543 (12)	0.0418 (4)

	U11	U22	U33	U12	U13	U23
O1	0.0551 (8)	0.0761 (8)	0.0638 (8)	0.0232 (6)	−0.0050 (6)	0.0014 (6)
O2	0.0439 (7)	0.0632 (7)	0.0729 (8)	−0.0078 (6)	0.0036 (5)	−0.0194 (6)
O3	0.0384 (6)	0.0511 (6)	0.0573 (7)	0.0031 (4)	0.0083 (5)	−0.0115 (5)
N1	0.0373 (7)	0.0501 (7)	0.0512 (8)	0.0040 (5)	0.0081 (6)	−0.0036 (6)
N2	0.0392 (7)	0.0486 (7)	0.0432 (7)	0.0003 (5)	0.0037 (5)	0.0044 (6)
C1	0.0456 (9)	0.0518 (9)	0.0405 (9)	0.0050 (7)	0.0138 (7)	0.0039 (7)
C2	0.0617 (11)	0.0583 (11)	0.0589 (11)	0.0074 (8)	0.0049 (8)	0.0115 (8)
C3	0.0826 (14)	0.0581 (11)	0.0687 (12)	0.0148 (10)	0.0184 (10)	0.0180 (9)
C4	0.0781 (13)	0.0476 (10)	0.0750 (13)	−0.0020 (9)	0.0333 (10)	0.0026 (9)
C5	0.0538 (11)	0.0612 (11)	0.0772 (13)	−0.0070 (8)	0.0189 (9)	−0.0040 (9)
C6	0.0464 (9)	0.0532 (9)	0.0594 (10)	0.0026 (7)	0.0123 (7)	0.0050 (8)
C7	0.0364 (8)	0.0518 (9)	0.0398 (8)	0.0053 (6)	0.0088 (6)	0.0034 (7)
C8	0.0523 (10)	0.0549 (9)	0.0372 (8)	0.0053 (7)	0.0047 (7)	0.0028 (7)
C9	0.0441 (9)	0.0546 (9)	0.0421 (9)	0.0077 (7)	−0.0031 (7)	−0.0086 (7)
C10	0.0390 (9)	0.0538 (9)	0.0696 (11)	−0.0012 (7)	0.0129 (8)	−0.0137 (8)
C11	0.0364 (8)	0.0487 (8)	0.0433 (9)	0.0009 (7)	0.0025 (6)	−0.0019 (7)
C12	0.0610 (11)	0.0597 (10)	0.0570 (11)	0.0105 (8)	0.0082 (8)	−0.0162 (8)
C13	0.0651 (12)	0.0721 (12)	0.0681 (12)	0.0205 (9)	0.0253 (9)	0.0010 (9)
C14	0.0413 (8)	0.0456 (8)	0.0383 (8)	0.0031 (6)	0.0085 (6)	−0.0049 (6)
C15	0.0521 (10)	0.0487 (9)	0.0536 (10)	−0.0049 (7)	0.0108 (7)	−0.0090 (7)
C16	0.0766 (13)	0.0426 (9)	0.0599 (11)	−0.0012 (8)	0.0115 (9)	−0.0004 (8)
C17	0.0711 (12)	0.0516 (10)	0.0552 (10)	0.0119 (9)	0.0053 (9)	0.0088 (8)
C18	0.0480 (9)	0.0592 (10)	0.0498 (10)	0.0056 (7)	0.0019 (7)	0.0078 (8)
C19	0.0430 (8)	0.0473 (8)	0.0349 (8)	0.0009 (7)	0.0050 (6)	−0.0007 (6)

O1—C9	1.2207 (17)	C8—C9	1.496 (2)
O2—C11	1.1955 (17)	C8—H8A	0.9700
O3—C11	1.3281 (17)	C8—H8B	0.9700
O3—C12	1.4537 (17)	C10—C11	1.502 (2)
N1—C9	1.363 (2)	C10—H10A	0.9700
N1—C14	1.4224 (17)	C10—H10B	0.9700
N1—C10	1.4625 (19)	C12—C13	1.489 (2)
N2—C7	1.2805 (18)	C12—H12A	0.9700
N2—C19	1.4102 (18)	C12—H12B	0.9700
C1—C6	1.383 (2)	C13—H13A	0.9600
C1—C2	1.387 (2)	C13—H13B	0.9600
C1—C7	1.480 (2)	C13—H13C	0.9600
C2—C3	1.378 (2)	C14—C15	1.395 (2)
C2—H2	0.9300	C14—C19	1.4005 (19)
C3—C4	1.366 (3)	C15—C16	1.368 (2)
C3—H3	0.9300	C15—H15	0.9300
C4—C5	1.374 (2)	C16—C17	1.375 (2)
C4—H4	0.9300	C16—H16	0.9300
C5—C6	1.381 (2)	C17—C18	1.374 (2)
C5—H5	0.9300	C17—H17	0.9300
C6—H6	0.9300	C18—C19	1.398 (2)
C7—C8	1.515 (2)	C18—H18	0.9300
C11—O3—C12	115.86 (12)	C11—C10—H10A	109.5
C9—N1—C14	124.03 (13)	N1—C10—H10B	109.5
C9—N1—C10	116.31 (12)	C11—C10—H10B	109.5
C14—N1—C10	119.65 (12)	H10A—C10—H10B	108.0
C7—N2—C19	119.99 (13)	O2—C11—O3	125.19 (14)
C6—C1—C2	118.26 (15)	O2—C11—C10	124.83 (14)
C6—C1—C7	120.43 (14)	O3—C11—C10	109.95 (12)
C2—C1—C7	121.26 (14)	O3—C12—C13	107.85 (13)
C3—C2—C1	120.61 (17)	O3—C12—H12A	110.1
C3—C2—H2	119.7	C13—C12—H12A	110.1
C1—C2—H2	119.7	O3—C12—H12B	110.1
C4—C3—C2	120.46 (17)	C13—C12—H12B	110.1
C4—C3—H3	119.8	H12A—C12—H12B	108.4
C2—C3—H3	119.8	C12—C13—H13A	109.5
C3—C4—C5	119.83 (17)	C12—C13—H13B	109.5
C3—C4—H4	120.1	H13A—C13—H13B	109.5
C5—C4—H4	120.1	C12—C13—H13C	109.5
C4—C5—C6	119.99 (17)	H13A—C13—H13C	109.5
C4—C5—H5	120.0	H13B—C13—H13C	109.5
C6—C5—H5	120.0	C15—C14—C19	119.38 (13)
C5—C6—C1	120.83 (16)	C15—C14—N1	118.26 (13)
C5—C6—H6	119.6	C19—C14—N1	122.32 (13)
C1—C6—H6	119.6	C16—C15—C14	120.93 (16)
N2—C7—C1	118.53 (13)	C16—C15—H15	119.5
N2—C7—C8	121.78 (13)	C14—C15—H15	119.5
C1—C7—C8	119.65 (13)	C15—C16—C17	120.26 (15)
C9—C8—C7	107.47 (12)	C15—C16—H16	119.9
C9—C8—H8A	110.2	C17—C16—H16	119.9
C7—C8—H8A	110.2	C18—C17—C16	119.74 (16)
C9—C8—H8B	110.2	C18—C17—H17	120.1
C7—C8—H8B	110.2	C16—C17—H17	120.1
H8A—C8—H8B	108.5	C17—C18—C19	121.43 (16)
O1—C9—N1	121.36 (15)	C17—C18—H18	119.3
O1—C9—C8	123.30 (15)	C19—C18—H18	119.3
N1—C9—C8	115.23 (13)	C18—C19—C14	118.24 (13)
N1—C10—C11	110.92 (12)	C18—C19—N2	116.89 (13)
N1—C10—H10A	109.5	C14—C19—N2	124.72 (13)
C6—C1—C2—C3	0.4 (2)	C14—N1—C10—C11	−116.19 (14)
C7—C1—C2—C3	−177.05 (15)	C12—O3—C11—O2	−1.0 (2)
C1—C2—C3—C4	−1.3 (3)	C12—O3—C11—C10	−179.08 (14)
C2—C3—C4—C5	1.0 (3)	N1—C10—C11—O2	20.5 (2)
C3—C4—C5—C6	0.2 (3)	N1—C10—C11—O3	−161.39 (13)
C4—C5—C6—C1	−1.1 (3)	C11—O3—C12—C13	−169.68 (13)
C2—C1—C6—C5	0.9 (2)	C9—N1—C14—C15	135.77 (15)
C7—C1—C6—C5	178.28 (15)	C10—N1—C14—C15	−43.45 (18)
C19—N2—C7—C1	−175.16 (12)	C9—N1—C14—C19	−46.5 (2)
C19—N2—C7—C8	2.8 (2)	C10—N1—C14—C19	134.31 (15)
C6—C1—C7—N2	−26.6 (2)	C19—C14—C15—C16	1.0 (2)
C2—C1—C7—N2	150.72 (15)	N1—C14—C15—C16	178.85 (13)
C6—C1—C7—C8	155.40 (14)	C14—C15—C16—C17	−0.2 (2)
C2—C1—C7—C8	−27.3 (2)	C15—C16—C17—C18	−0.8 (3)
N2—C7—C8—C9	−74.71 (17)	C16—C17—C18—C19	1.2 (3)
C1—C7—C8—C9	103.20 (15)	C17—C18—C19—C14	−0.4 (2)
C14—N1—C9—O1	−176.16 (13)	C17—C18—C19—N2	−176.23 (14)
C10—N1—C9—O1	3.1 (2)	C15—C14—C19—C18	−0.7 (2)
C14—N1—C9—C8	7.5 (2)	N1—C14—C19—C18	−178.44 (13)
C10—N1—C9—C8	−173.24 (12)	C15—C14—C19—N2	174.79 (14)
C7—C8—C9—O1	−111.25 (16)	N1—C14—C19—N2	−2.9 (2)
C7—C8—C9—N1	65.00 (16)	C7—N2—C19—C18	−140.71 (15)
C9—N1—C10—C11	64.53 (18)	C7—N2—C19—C14	43.7 (2)