5-Acetyl-3-hy-droxy-4-phenyl-4,5-dihydro-1H-1,5-benzodiazepin-2(3H)-one.

In the title compound, C(17)H(16)N(2)O(3), the seven-membered diazepine ring adopts a boat conformation with the hy-droxy-substituted C atom at the prow and fused benzene ring C atoms at the stern. The phenyl substituent occupies an equatorial position. The amino group of the ring system is a hydrogen-bond donor to the oxo O atom of an inversion-related mol-ecule, and the hy-droxy group is a hydrogen-bond donor to the acetyl O atom of another inversion-related mol-ecule. The two hydrogen bonds generate a ribbon motif parallel to [10[Formula: see text]] in the crystal structure.

Related literature

For a related 1,5-benzodiazepin-2(3H)-one structure, see: Rida et al. (2011 ▶).

Experimental

Crystal data

C17H16N2O3

M = 296.32

Triclinic,

a = 8.9710 (1) Å

b = 9.3142 (1) Å

c = 9.4129 (1) Å

α = 81.563 (1)°

β = 68.921 (1)°

γ = 80.146 (1)°

V = 719.95 (1) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.29 × 0.23 × 0.18 mm

Data collection

Bruker APEX DUO diffractometer

19110 measured reflections

4203 independent reflections

3584 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.149

S = 1.02

4203 reflections

208 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.30 e Å−3

Δρmin = −0.27 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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 datablock(s) global, I. DOI: 10.1107/S1600536811047878/lh5376sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811047878/lh5376Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811047878/lh5376Isup3.cml

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

C17H16N2O3	Z = 2
Mr = 296.32	F(000) = 312
Triclinic, P1	Dx = 1.367 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.9710 (1) Å	Cell parameters from 9950 reflections
b = 9.3142 (1) Å	θ = 2.2–34.5°
c = 9.4129 (1) Å	µ = 0.10 mm−1
α = 81.563 (1)°	T = 293 K
β = 68.921 (1)°	Prism, colorless
γ = 80.146 (1)°	0.29 × 0.23 × 0.18 mm
V = 719.95 (1) Å3

Bruker APEX DUO diffractometer	3584 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.024
graphite	θmax = 30.0°, θmin = 2.2°
ω scans	h = −12→12
19110 measured reflections	k = −13→13
4203 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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.149	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0876P)2 + 0.1414P] where P = (Fo2 + 2Fc2)/3
4203 reflections	(Δ/σ)max = 0.001
208 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.27 e Å−3

	x	y	z	Uiso*/Ueq
O1	0.18813 (12)	0.41278 (9)	0.39332 (11)	0.0488 (2)
O2	0.50968 (12)	0.39185 (9)	0.34285 (10)	0.0430 (2)
O3	0.41433 (13)	0.74792 (11)	−0.06449 (10)	0.0513 (2)
N1	0.14350 (13)	0.64817 (10)	0.44597 (12)	0.0426 (2)
N2	0.37829 (11)	0.75893 (9)	0.18338 (9)	0.03178 (19)
C1	0.19921 (15)	0.78134 (12)	0.44620 (13)	0.0406 (3)
C2	0.1358 (2)	0.85962 (16)	0.57413 (16)	0.0656 (5)
H2A	0.0547	0.8253	0.6599	0.079*
C3	0.1927 (3)	0.98823 (18)	0.5745 (2)	0.0756 (6)
H3	0.1499	1.0396	0.6609	0.091*
C4	0.3123 (2)	1.04144 (16)	0.4483 (2)	0.0639 (4)
H4	0.3501	1.1280	0.4496	0.077*
C5	0.37548 (17)	0.96508 (13)	0.31996 (15)	0.0468 (3)
H5	0.4570	0.9999	0.2349	0.056*
C6	0.31790 (13)	0.83653 (11)	0.31723 (12)	0.0346 (2)
C7	0.24114 (14)	0.52550 (11)	0.39399 (12)	0.0363 (2)
C8	0.42230 (13)	0.53221 (11)	0.34285 (11)	0.0329 (2)
H8	0.4407	0.5843	0.4171	0.039*
C9	0.48415 (12)	0.61900 (10)	0.18549 (10)	0.0293 (2)
H9	0.4758	0.5617	0.1099	0.035*
C10	0.65889 (13)	0.64317 (11)	0.13784 (12)	0.0345 (2)
C11	0.72509 (17)	0.67606 (14)	0.24003 (18)	0.0493 (3)
H11	0.6625	0.6825	0.3425	0.059*
C12	0.8864 (2)	0.69927 (17)	0.1874 (3)	0.0685 (5)
H12	0.9311	0.7212	0.2555	0.082*
C13	0.98046 (18)	0.69010 (16)	0.0359 (3)	0.0722 (6)
H13	1.0876	0.7066	0.0020	0.087*
C14	0.91519 (18)	0.65653 (16)	−0.0649 (2)	0.0624 (4)
H14	0.9786	0.6493	−0.1671	0.075*
C15	0.75549 (15)	0.63361 (13)	−0.01454 (15)	0.0450 (3)
H15	0.7120	0.6115	−0.0835	0.054*
C16	0.35154 (14)	0.81314 (12)	0.05077 (12)	0.0371 (2)
C17	0.24042 (18)	0.95367 (15)	0.05114 (17)	0.0529 (3)
H17A	0.1983	0.9597	−0.0303	0.079*
H17B	0.2988	1.0350	0.0367	0.079*
H17C	0.1532	0.9560	0.1472	0.079*
H1	0.042 (2)	0.635 (2)	0.498 (2)	0.057 (5)*
H2	0.517 (2)	0.353 (2)	0.266 (2)	0.065 (5)*

	U11	U22	U33	U12	U13	U23
O1	0.0575 (5)	0.0342 (4)	0.0491 (5)	−0.0188 (4)	−0.0046 (4)	−0.0074 (3)
O2	0.0622 (5)	0.0290 (4)	0.0370 (4)	0.0006 (3)	−0.0196 (4)	−0.0017 (3)
O3	0.0650 (6)	0.0559 (6)	0.0302 (4)	0.0024 (4)	−0.0175 (4)	−0.0038 (4)
N1	0.0456 (5)	0.0311 (5)	0.0406 (5)	−0.0124 (4)	0.0015 (4)	−0.0043 (4)
N2	0.0399 (4)	0.0259 (4)	0.0254 (4)	−0.0040 (3)	−0.0067 (3)	−0.0015 (3)
C1	0.0511 (6)	0.0282 (5)	0.0330 (5)	−0.0082 (4)	−0.0009 (4)	−0.0050 (4)
C2	0.0924 (12)	0.0422 (7)	0.0385 (6)	−0.0147 (7)	0.0118 (7)	−0.0120 (5)
C3	0.1156 (15)	0.0465 (8)	0.0507 (8)	−0.0142 (9)	−0.0023 (9)	−0.0248 (6)
C4	0.0897 (11)	0.0368 (6)	0.0631 (9)	−0.0180 (7)	−0.0139 (8)	−0.0185 (6)
C5	0.0571 (7)	0.0316 (5)	0.0465 (6)	−0.0148 (5)	−0.0066 (5)	−0.0058 (4)
C6	0.0432 (5)	0.0258 (4)	0.0298 (5)	−0.0061 (4)	−0.0052 (4)	−0.0040 (3)
C7	0.0491 (6)	0.0288 (5)	0.0270 (4)	−0.0114 (4)	−0.0062 (4)	−0.0004 (3)
C8	0.0469 (5)	0.0254 (4)	0.0259 (4)	−0.0063 (4)	−0.0116 (4)	−0.0009 (3)
C9	0.0385 (5)	0.0249 (4)	0.0240 (4)	−0.0057 (3)	−0.0091 (3)	−0.0028 (3)
C10	0.0389 (5)	0.0254 (4)	0.0381 (5)	−0.0054 (4)	−0.0111 (4)	−0.0034 (4)
C11	0.0556 (7)	0.0410 (6)	0.0608 (8)	−0.0076 (5)	−0.0281 (6)	−0.0112 (5)
C12	0.0610 (9)	0.0441 (7)	0.1198 (16)	−0.0066 (6)	−0.0511 (10)	−0.0159 (8)
C13	0.0406 (7)	0.0385 (7)	0.1285 (17)	−0.0077 (5)	−0.0178 (9)	−0.0063 (8)
C14	0.0456 (7)	0.0411 (7)	0.0778 (10)	−0.0069 (5)	0.0034 (7)	0.0027 (6)
C15	0.0454 (6)	0.0376 (6)	0.0426 (6)	−0.0069 (5)	−0.0042 (5)	−0.0013 (4)
C16	0.0414 (5)	0.0350 (5)	0.0313 (5)	−0.0071 (4)	−0.0097 (4)	0.0036 (4)
C17	0.0566 (7)	0.0426 (6)	0.0510 (7)	0.0028 (5)	−0.0171 (6)	0.0076 (5)

O1—C7	1.2261 (13)	C7—C8	1.5297 (16)
O2—C8	1.4046 (13)	C8—C9	1.5382 (13)
O2—H2	0.83 (2)	C8—H8	0.9800
O3—C16	1.2247 (14)	C9—C10	1.5148 (14)
N1—C7	1.3510 (15)	C9—H9	0.9800
N1—C1	1.4149 (14)	C10—C11	1.3897 (17)
N1—H1	0.89 (2)	C10—C15	1.3905 (16)
N2—C16	1.3637 (14)	C11—C12	1.395 (2)
N2—C6	1.4302 (13)	C11—H11	0.9300
N2—C9	1.4776 (12)	C12—C13	1.378 (3)
C1—C2	1.3886 (17)	C12—H12	0.9300
C1—C6	1.3950 (15)	C13—C14	1.375 (3)
C2—C3	1.381 (2)	C13—H13	0.9300
C2—H2A	0.9300	C14—C15	1.3818 (19)
C3—C4	1.378 (3)	C14—H14	0.9300
C3—H3	0.9300	C15—H15	0.9300
C4—C5	1.3814 (19)	C16—C17	1.5031 (17)
C4—H4	0.9300	C17—H17A	0.9600
C5—C6	1.3897 (15)	C17—H17B	0.9600
C5—H5	0.9300	C17—H17C	0.9600
C8—O2—H2	109.8 (14)	N2—C9—C10	111.43 (8)
C7—N1—C1	124.00 (10)	N2—C9—C8	109.66 (8)
C7—N1—H1	114.4 (12)	C10—C9—C8	113.46 (9)
C1—N1—H1	120.4 (12)	N2—C9—H9	107.3
C16—N2—C6	122.88 (9)	C10—C9—H9	107.3
C16—N2—C9	118.55 (8)	C8—C9—H9	107.3
C6—N2—C9	118.41 (8)	C11—C10—C15	119.09 (12)
C2—C1—C6	119.01 (11)	C11—C10—C9	122.52 (10)
C2—C1—N1	120.58 (11)	C15—C10—C9	118.38 (10)
C6—C1—N1	120.40 (10)	C10—C11—C12	119.33 (15)
C3—C2—C1	120.25 (13)	C10—C11—H11	120.3
C3—C2—H2A	119.9	C12—C11—H11	120.3
C1—C2—H2A	119.9	C13—C12—C11	120.92 (16)
C4—C3—C2	120.84 (13)	C13—C12—H12	119.5
C4—C3—H3	119.6	C11—C12—H12	119.5
C2—C3—H3	119.6	C14—C13—C12	119.71 (14)
C3—C4—C5	119.44 (13)	C14—C13—H13	120.1
C3—C4—H4	120.3	C12—C13—H13	120.1
C5—C4—H4	120.3	C13—C14—C15	120.03 (16)
C4—C5—C6	120.37 (12)	C13—C14—H14	120.0
C4—C5—H5	119.8	C15—C14—H14	120.0
C6—C5—H5	119.8	C14—C15—C10	120.91 (14)
C5—C6—C1	120.05 (10)	C14—C15—H15	119.5
C5—C6—N2	121.01 (10)	C10—C15—H15	119.5
C1—C6—N2	118.94 (9)	O3—C16—N2	120.90 (10)
O1—C7—N1	122.08 (11)	O3—C16—C17	121.05 (11)
O1—C7—C8	121.49 (10)	N2—C16—C17	118.04 (10)
N1—C7—C8	116.36 (9)	C16—C17—H17A	109.5
O2—C8—C7	111.68 (8)	C16—C17—H17B	109.5
O2—C8—C9	110.91 (8)	H17A—C17—H17B	109.5
C7—C8—C9	111.53 (9)	C16—C17—H17C	109.5
O2—C8—H8	107.5	H17A—C17—H17C	109.5
C7—C8—H8	107.5	H17B—C17—H17C	109.5
C9—C8—H8	107.5
C7—N1—C1—C2	−134.65 (15)	C6—N2—C9—C10	−87.10 (10)
C7—N1—C1—C6	45.87 (19)	C16—N2—C9—C8	−145.05 (10)
C6—C1—C2—C3	−1.6 (3)	C6—N2—C9—C8	39.37 (12)
N1—C1—C2—C3	178.87 (17)	O2—C8—C9—N2	173.40 (8)
C1—C2—C3—C4	0.3 (3)	C7—C8—C9—N2	48.24 (11)
C2—C3—C4—C5	0.1 (3)	O2—C8—C9—C10	−61.29 (11)
C3—C4—C5—C6	0.7 (3)	C7—C8—C9—C10	173.56 (8)
C4—C5—C6—C1	−2.0 (2)	N2—C9—C10—C11	84.57 (12)
C4—C5—C6—N2	177.86 (14)	C8—C9—C10—C11	−39.79 (14)
C2—C1—C6—C5	2.5 (2)	N2—C9—C10—C15	−94.64 (11)
N1—C1—C6—C5	−178.04 (12)	C8—C9—C10—C15	140.99 (10)
C2—C1—C6—N2	−177.42 (13)	C15—C10—C11—C12	0.26 (18)
N1—C1—C6—N2	2.06 (18)	C9—C10—C11—C12	−178.95 (11)
C16—N2—C6—C5	−67.48 (16)	C10—C11—C12—C13	0.0 (2)
C9—N2—C6—C5	107.89 (12)	C11—C12—C13—C14	−0.5 (2)
C16—N2—C6—C1	112.42 (13)	C12—C13—C14—C15	0.7 (2)
C9—N2—C6—C1	−72.21 (14)	C13—C14—C15—C10	−0.4 (2)
C1—N1—C7—O1	−178.75 (11)	C11—C10—C15—C14	−0.10 (18)
C1—N1—C7—C8	4.08 (17)	C9—C10—C15—C14	179.14 (11)
O1—C7—C8—O2	−18.12 (14)	C6—N2—C16—O3	175.01 (10)
N1—C7—C8—O2	159.07 (10)	C9—N2—C16—O3	−0.35 (16)
O1—C7—C8—C9	106.61 (11)	C6—N2—C16—C17	−6.10 (16)
N1—C7—C8—C9	−76.20 (12)	C9—N2—C16—C17	178.53 (10)
C16—N2—C9—C10	88.48 (11)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.89 (2)	2.04 (2)	2.924 (1)	175 (2)
O2—H2···O3ii	0.83 (2)	2.09 (2)	2.905 (1)	168 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.89 (2)	2.04 (2)	2.924 (1)	175 (2)
O2—H2⋯O3ii	0.83 (2)	2.09 (2)	2.905 (1)	168 (2)

Symmetry codes: (i) ; (ii) .