4-Phenyl-1H-1,5-benzodiazepin-2(3H)-one.

In the title compound, C15H12N2O, the phenyl ring makes a dihedral angle of 32.45 (9)° with the benzene ring of the 1,5-benzodiazepin-2-one unit. The seven-membered ring adopts a boat conformation with the methyl-ene group as the prow and the fused benzene-ring C atoms as the stern. In the crystal, inversion dimers linked by pairs of N-H⋯O hydrogen bonds generate R2(2)(8) loops. The dimers are further linked by C-H⋯O hydrogen bonds, so forming a column along the a-axis direction.

Related literature

For background to benzodiazepine compounds, see: McKernan (2000 ▶); Thakur et al. (2003 ▶). For related structures, see: Benelbaghdadi et al. (2003 ▶); Višnjevac et al. (2002 ▶).

Experimental

Crystal data

C15H12N2O

M = 236.27

Triclinic,

a = 4.6894 (5) Å

b = 10.8353 (13) Å

c = 11.7540 (13) Å

α = 77.721 (10)°

β = 83.805 (9)°

γ = 82.112 (10)°

V = 576.13 (12) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 123 K

0.35 × 0.09 × 0.06 mm

Data collection

Oxford Diffraction Xcalibur Eos CCD diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.928, T max = 1.000

4335 measured reflections

2584 independent reflections

1830 reflections with I > 2σI

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.140

S = 1.02

2584 reflections

167 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.24 e Å−3

Δρmin = −0.29 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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, 2012 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶) and PLATON.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681204651X/hb6983sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681204651X/hb6983Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S160053681204651X/hb6983Isup3.cml

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

C15H12N2O	Z = 2
Mr = 236.27	F(000) = 248
Triclinic, P1	Dx = 1.362 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 4.6894 (5) Å	Cell parameters from 1808 reflections
b = 10.8353 (13) Å	θ = 3.6–28.6°
c = 11.7540 (13) Å	µ = 0.09 mm−1
α = 77.721 (10)°	T = 123 K
β = 83.805 (9)°	Rod, colourless
γ = 82.112 (10)°	0.35 × 0.09 × 0.06 mm
V = 576.13 (12) Å3

Oxford Diffraction Xcalibur Eos CCD diffractometer	2584 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1830 reflections with I > 2σI
Graphite monochromator	Rint = 0.034
Detector resolution: 16.0727 pixels mm-1	θmax = 28.7°, θmin = 3.6°
ω scans	h = −5→5
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −13→14
Tmin = 0.928, Tmax = 1.000	l = −14→14
4335 measured reflections

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.140	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0553P)2 + 0.0566P] where P = (Fo2 + 2Fc2)/3
2584 reflections	(Δ/σ)max < 0.001
167 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.29 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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	0.5985 (3)	0.83316 (12)	−0.01502 (12)	0.0240 (4)
N1	0.2761 (3)	0.91004 (15)	0.11765 (15)	0.0196 (5)
N2	0.1807 (3)	0.67999 (15)	0.30340 (14)	0.0208 (5)
C1	0.2541 (4)	0.69700 (17)	0.09252 (17)	0.0198 (6)
C2	0.3919 (4)	0.81833 (18)	0.05942 (17)	0.0189 (6)
C3	0.0429 (4)	0.90428 (18)	0.20457 (17)	0.0191 (6)
C4	−0.1284 (4)	1.01875 (18)	0.21167 (18)	0.0223 (6)
C5	−0.3538 (4)	1.0235 (2)	0.29689 (19)	0.0265 (7)
C6	−0.4128 (4)	0.9137 (2)	0.37674 (19)	0.0264 (7)
C7	−0.2380 (4)	0.80156 (19)	0.37327 (18)	0.0238 (6)
C8	−0.0060 (4)	0.79387 (18)	0.28803 (17)	0.0198 (6)
C9	0.3135 (4)	0.63570 (17)	0.21650 (17)	0.0188 (6)
C10	0.5331 (4)	0.52265 (17)	0.24188 (17)	0.0187 (6)
C11	0.7291 (4)	0.48274 (18)	0.15578 (18)	0.0219 (6)
C12	0.9357 (4)	0.37853 (19)	0.18455 (19)	0.0255 (7)
C13	0.9510 (4)	0.31567 (19)	0.29879 (19)	0.0263 (7)
C14	0.7573 (4)	0.35380 (19)	0.38557 (19)	0.0265 (7)
C15	0.5496 (4)	0.45695 (18)	0.35707 (18)	0.0230 (6)
H1A	0.33500	0.63890	0.03940	0.0240*
H1B	0.04320	0.71540	0.08580	0.0240*
H1N	0.324 (4)	0.990 (2)	0.089 (2)	0.038 (6)*
H4	−0.08940	1.09410	0.15730	0.0270*
H5	−0.46890	1.10190	0.30100	0.0320*
H6	−0.57300	0.91620	0.43340	0.0320*
H7	−0.27520	0.72760	0.42990	0.0290*
H11	0.72190	0.52680	0.07690	0.0260*
H12	1.06670	0.35070	0.12510	0.0310*
H13	1.09520	0.24570	0.31820	0.0320*
H14	0.76660	0.30960	0.46430	0.0320*
H15	0.41690	0.48320	0.41680	0.0280*

	U11	U22	U33	U12	U13	U23
O1	0.0232 (7)	0.0258 (8)	0.0206 (8)	−0.0022 (6)	0.0039 (6)	−0.0025 (6)
N1	0.0205 (8)	0.0168 (8)	0.0207 (10)	−0.0034 (6)	0.0005 (7)	−0.0021 (7)
N2	0.0188 (8)	0.0212 (9)	0.0216 (10)	−0.0027 (6)	0.0008 (6)	−0.0033 (7)
C1	0.0198 (9)	0.0200 (10)	0.0200 (11)	−0.0020 (7)	−0.0025 (7)	−0.0048 (8)
C2	0.0188 (9)	0.0197 (10)	0.0175 (11)	−0.0005 (7)	−0.0061 (7)	−0.0008 (8)
C3	0.0151 (9)	0.0241 (10)	0.0199 (11)	−0.0041 (7)	−0.0007 (7)	−0.0079 (8)
C4	0.0225 (10)	0.0191 (10)	0.0251 (12)	−0.0032 (8)	−0.0028 (8)	−0.0033 (8)
C5	0.0205 (10)	0.0295 (11)	0.0309 (13)	0.0017 (8)	−0.0038 (8)	−0.0110 (10)
C6	0.0183 (10)	0.0351 (12)	0.0276 (12)	−0.0023 (8)	0.0015 (8)	−0.0125 (10)
C7	0.0189 (10)	0.0285 (11)	0.0239 (12)	−0.0061 (8)	0.0007 (8)	−0.0043 (9)
C8	0.0161 (9)	0.0224 (10)	0.0221 (11)	−0.0028 (7)	−0.0028 (8)	−0.0065 (8)
C9	0.0189 (9)	0.0197 (10)	0.0183 (11)	−0.0057 (7)	−0.0010 (7)	−0.0028 (8)
C10	0.0178 (9)	0.0188 (10)	0.0211 (11)	−0.0047 (7)	−0.0022 (7)	−0.0054 (8)
C11	0.0233 (10)	0.0239 (11)	0.0188 (11)	−0.0049 (8)	−0.0010 (8)	−0.0042 (8)
C12	0.0221 (10)	0.0271 (11)	0.0284 (13)	−0.0021 (8)	0.0020 (8)	−0.0106 (9)
C13	0.0207 (10)	0.0248 (11)	0.0336 (13)	−0.0003 (8)	−0.0039 (8)	−0.0068 (9)
C14	0.0278 (11)	0.0270 (11)	0.0229 (12)	−0.0022 (8)	−0.0033 (8)	−0.0012 (9)
C15	0.0232 (10)	0.0249 (11)	0.0206 (11)	−0.0019 (8)	−0.0008 (8)	−0.0053 (9)

O1—C2	1.237 (2)	C10—C11	1.390 (3)
N1—C2	1.346 (3)	C11—C12	1.391 (3)
N1—C3	1.412 (3)	C12—C13	1.375 (3)
N2—C8	1.402 (3)	C13—C14	1.383 (3)
N2—C9	1.285 (3)	C14—C15	1.387 (3)
N1—H1N	0.91 (2)	C1—H1A	0.9900
C1—C9	1.506 (3)	C1—H1B	0.9900
C1—C2	1.503 (3)	C4—H4	0.9500
C3—C8	1.405 (3)	C5—H5	0.9500
C3—C4	1.395 (3)	C6—H6	0.9500
C4—C5	1.379 (3)	C7—H7	0.9500
C5—C6	1.390 (3)	C11—H11	0.9500
C6—C7	1.375 (3)	C12—H12	0.9500
C7—C8	1.404 (3)	C13—H13	0.9500
C9—C10	1.488 (3)	C14—H14	0.9500
C10—C15	1.394 (3)	C15—H15	0.9500
C2—N1—C3	127.34 (17)	C12—C13—C14	120.27 (19)
C8—N2—C9	122.03 (17)	C13—C14—C15	119.7 (2)
C2—N1—H1N	117.5 (14)	C10—C15—C14	120.81 (19)
C3—N1—H1N	113.8 (13)	C2—C1—H1A	110.00
C2—C1—C9	108.46 (16)	C2—C1—H1B	110.00
O1—C2—C1	122.81 (17)	C9—C1—H1A	110.00
O1—C2—N1	122.06 (18)	C9—C1—H1B	110.00
N1—C2—C1	115.13 (16)	H1A—C1—H1B	108.00
N1—C3—C8	123.51 (17)	C3—C4—H4	120.00
C4—C3—C8	119.81 (18)	C5—C4—H4	120.00
N1—C3—C4	116.43 (17)	C4—C5—H5	120.00
C3—C4—C5	120.61 (19)	C6—C5—H5	120.00
C4—C5—C6	120.12 (19)	C5—C6—H6	120.00
C5—C6—C7	119.63 (19)	C7—C6—H6	120.00
C6—C7—C8	121.54 (19)	C6—C7—H7	119.00
C3—C8—C7	118.18 (18)	C8—C7—H7	119.00
N2—C8—C7	116.13 (17)	C10—C11—H11	120.00
N2—C8—C3	125.11 (17)	C12—C11—H11	120.00
N2—C9—C1	121.42 (17)	C11—C12—H12	120.00
N2—C9—C10	117.88 (17)	C13—C12—H12	120.00
C1—C9—C10	120.69 (16)	C12—C13—H13	120.00
C9—C10—C11	122.52 (18)	C14—C13—H13	120.00
C11—C10—C15	118.72 (18)	C13—C14—H14	120.00
C9—C10—C15	118.73 (17)	C15—C14—H14	120.00
C10—C11—C12	120.32 (19)	C10—C15—H15	120.00
C11—C12—C13	120.21 (19)	C14—C15—H15	120.00
C3—N1—C2—O1	−179.53 (18)	C3—C4—C5—C6	−0.1 (3)
C3—N1—C2—C1	−0.2 (3)	C4—C5—C6—C7	2.7 (3)
C2—N1—C3—C4	−149.39 (19)	C5—C6—C7—C8	−2.3 (3)
C2—N1—C3—C8	36.4 (3)	C6—C7—C8—N2	171.13 (18)
C9—N2—C8—C3	−40.1 (3)	C6—C7—C8—C3	−0.6 (3)
C9—N2—C8—C7	148.81 (19)	N2—C9—C10—C11	−166.64 (18)
C8—N2—C9—C1	−6.0 (3)	N2—C9—C10—C15	11.0 (3)
C8—N2—C9—C10	172.89 (17)	C1—C9—C10—C11	12.3 (3)
C9—C1—C2—O1	112.8 (2)	C1—C9—C10—C15	−170.04 (17)
C9—C1—C2—N1	−66.6 (2)	C9—C10—C11—C12	178.16 (18)
C2—C1—C9—N2	74.3 (2)	C15—C10—C11—C12	0.5 (3)
C2—C1—C9—C10	−104.6 (2)	C9—C10—C15—C14	−177.71 (18)
N1—C3—C4—C5	−177.32 (18)	C11—C10—C15—C14	0.0 (3)
C8—C3—C4—C5	−2.9 (3)	C10—C11—C12—C13	−1.2 (3)
N1—C3—C8—N2	6.3 (3)	C11—C12—C13—C14	1.4 (3)
N1—C3—C8—C7	177.21 (18)	C12—C13—C14—C15	−0.9 (3)
C4—C3—C8—N2	−167.75 (18)	C13—C14—C15—C10	0.1 (3)
C4—C3—C8—C7	3.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.91 (2)	1.99 (2)	2.900 (2)	175 (2)
C1—H1B···O1ii	0.99	2.56	3.468 (2)	153

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.91 (2)	1.99 (2)	2.900 (2)	175 (2)
C1—H1B⋯O1ii	0.99	2.56	3.468 (2)	153

Symmetry codes: (i) ; (ii) .