N-(2-Oxo-2-phenyl-acet-yl)benzamide.

In the title compound, C(15)H(11)NO(3), the two essentially planar benzaldehyde groups [maximum deviations = 0.0487 (12) and 0.0205 (10) Å] are inclined at a dihedral angle of 72.64 (6)° with respect to each other. The bridging C-C-N-C torsion angle is 22.58 (18)°. In the crystal, inter-molecular bifurcated acceptor N-H⋯O and C-H⋯O hydrogen bonds link inversion-related mol-ecules into dimers incorporating R(1) (2)(7) and R(2) (2)(8) ring motifs. The crystal structure is further stabilized by weak inter-molecular C-H⋯π inter-actions.

Related literature

For general background to and applications of the title benzamide compound, see: Haffner & Ulrich (2010 ▶); Lavanya & Rao (2010 ▶); Magarl et al. (2010 ▶). For graph-set descriptions of hydrogen-bond ring motifs, see: Bernstein et al. (1995 ▶). For related benzamide structures, see: Jotani et al. (2010 ▶); Fu et al. (1998 ▶); Gallagher et al. (2009 ▶). For related diketone structures, see: Cheah et al. (2008 ▶); Hartung et al. (2004 ▶). For standard bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C15H11NO3

M = 253.25

Monoclinic,

a = 5.7215 (1) Å

b = 10.7241 (1) Å

c = 20.6710 (3) Å

β = 98.255 (1)°

V = 1255.19 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.36 × 0.33 × 0.27 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.967, T max = 0.975

13904 measured reflections

3624 independent reflections

2549 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.124

S = 1.03

3624 reflections

176 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.19 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681005258X/lh5192sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681005258X/lh5192Isup2.hkl

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

C15H11NO3	F(000) = 528
Mr = 253.25	Dx = 1.340 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3981 reflections
a = 5.7215 (1) Å	θ = 2.8–28.7°
b = 10.7241 (1) Å	µ = 0.09 mm−1
c = 20.6710 (3) Å	T = 293 K
β = 98.255 (1)°	Block, colourless
V = 1255.19 (3) Å3	0.36 × 0.33 × 0.27 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	3624 independent reflections
Radiation source: fine-focus sealed tube	2549 reflections with I > 2σ(I)
graphite	Rint = 0.025
φ and ω scans	θmax = 30.1°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −8→7
Tmin = 0.967, Tmax = 0.975	k = −15→14
13904 measured reflections	l = −28→29

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0558P)2 + 0.1732P] where P = (Fo2 + 2Fc2)/3
3624 reflections	(Δ/σ)max = 0.001
176 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.19 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) 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	0.09882 (19)	0.34229 (9)	0.84139 (5)	0.0559 (3)
O2	0.55891 (18)	0.43948 (9)	0.92521 (5)	0.0541 (3)
O3	0.15170 (19)	0.15978 (8)	0.95510 (5)	0.0526 (3)
N1	0.2998 (2)	0.34922 (9)	0.98421 (5)	0.0425 (3)
C1	0.3026 (3)	0.14025 (14)	0.78023 (7)	0.0555 (4)
H1A	0.1544	0.1668	0.7607	0.067*
C2	0.4136 (4)	0.04282 (16)	0.75346 (8)	0.0682 (5)
H2A	0.3393	0.0029	0.7161	0.082*
C3	0.6340 (3)	0.00455 (15)	0.78184 (8)	0.0658 (5)
H3A	0.7078	−0.0613	0.7636	0.079*
C4	0.7464 (3)	0.06306 (15)	0.83711 (9)	0.0632 (4)
H4A	0.8964	0.0375	0.8557	0.076*
C5	0.6352 (3)	0.15980 (13)	0.86475 (7)	0.0520 (3)
H5A	0.7098	0.1988	0.9023	0.062*
C6	0.4132 (2)	0.19867 (11)	0.83662 (6)	0.0409 (3)
C7	0.2867 (2)	0.29847 (11)	0.86611 (6)	0.0399 (3)
C8	0.4020 (2)	0.36431 (10)	0.92888 (6)	0.0401 (3)
C9	0.1548 (2)	0.24758 (10)	0.99227 (6)	0.0387 (3)
C10	0.0059 (2)	0.25238 (10)	1.04531 (6)	0.0383 (3)
C11	−0.0018 (3)	0.35326 (11)	1.08721 (6)	0.0462 (3)
H11A	0.0917	0.4230	1.0833	0.055*
C12	−0.1486 (3)	0.34962 (13)	1.13475 (7)	0.0542 (4)
H12A	−0.1524	0.4168	1.1630	0.065*
C13	−0.2892 (3)	0.24711 (14)	1.14054 (8)	0.0612 (4)
H13A	−0.3876	0.2453	1.1727	0.073*
C14	−0.2843 (3)	0.14727 (14)	1.09876 (9)	0.0648 (4)
H14A	−0.3802	0.0784	1.1024	0.078*
C15	−0.1369 (3)	0.14978 (12)	1.05150 (7)	0.0527 (4)
H15A	−0.1332	0.0821	1.0235	0.063*
H1N1	0.337 (3)	0.4056 (15)	1.0148 (8)	0.055 (4)*

	U11	U22	U33	U12	U13	U23
O1	0.0567 (6)	0.0528 (6)	0.0559 (6)	−0.0008 (5)	0.0003 (5)	0.0004 (4)
O2	0.0593 (6)	0.0509 (5)	0.0563 (6)	−0.0261 (5)	0.0226 (5)	−0.0140 (4)
O3	0.0720 (7)	0.0380 (4)	0.0527 (5)	−0.0164 (4)	0.0258 (5)	−0.0117 (4)
N1	0.0522 (7)	0.0383 (5)	0.0390 (5)	−0.0163 (5)	0.0128 (5)	−0.0091 (4)
C1	0.0681 (10)	0.0593 (8)	0.0386 (6)	−0.0096 (7)	0.0057 (6)	−0.0075 (6)
C2	0.0970 (14)	0.0671 (10)	0.0431 (7)	−0.0139 (9)	0.0193 (8)	−0.0190 (7)
C3	0.0892 (13)	0.0541 (8)	0.0629 (9)	−0.0041 (8)	0.0409 (9)	−0.0113 (7)
C4	0.0576 (9)	0.0647 (9)	0.0715 (10)	0.0001 (7)	0.0234 (8)	−0.0067 (8)
C5	0.0504 (8)	0.0545 (8)	0.0522 (8)	−0.0094 (6)	0.0112 (6)	−0.0112 (6)
C6	0.0483 (7)	0.0412 (6)	0.0352 (6)	−0.0120 (5)	0.0129 (5)	−0.0029 (5)
C7	0.0466 (7)	0.0372 (6)	0.0366 (6)	−0.0123 (5)	0.0082 (5)	0.0006 (4)
C8	0.0454 (7)	0.0333 (5)	0.0431 (6)	−0.0090 (5)	0.0112 (5)	−0.0045 (4)
C9	0.0455 (7)	0.0334 (5)	0.0378 (6)	−0.0068 (5)	0.0077 (5)	−0.0012 (4)
C10	0.0444 (7)	0.0335 (5)	0.0380 (6)	−0.0031 (5)	0.0093 (5)	0.0024 (4)
C11	0.0559 (8)	0.0383 (6)	0.0459 (7)	−0.0074 (6)	0.0128 (6)	−0.0036 (5)
C12	0.0681 (10)	0.0472 (7)	0.0510 (8)	0.0018 (7)	0.0217 (7)	−0.0048 (6)
C13	0.0729 (10)	0.0553 (8)	0.0634 (9)	0.0031 (7)	0.0371 (8)	0.0073 (7)
C14	0.0778 (11)	0.0457 (7)	0.0793 (11)	−0.0143 (7)	0.0402 (9)	0.0038 (7)
C15	0.0675 (9)	0.0357 (6)	0.0598 (8)	−0.0096 (6)	0.0261 (7)	−0.0030 (5)

O1—C7	1.2164 (16)	C5—H5A	0.9300
O2—C8	1.2170 (14)	C6—C7	1.4723 (18)
O3—C9	1.2138 (14)	C7—C8	1.5401 (16)
N1—C8	1.3667 (16)	C9—C10	1.4828 (17)
N1—C9	1.3943 (15)	C10—C15	1.3873 (17)
N1—H1N1	0.879 (16)	C10—C11	1.3904 (17)
C1—C2	1.379 (2)	C11—C12	1.3818 (19)
C1—C6	1.3929 (18)	C11—H11A	0.9300
C1—H1A	0.9300	C12—C13	1.378 (2)
C2—C3	1.375 (3)	C12—H12A	0.9300
C2—H2A	0.9300	C13—C14	1.378 (2)
C3—C4	1.379 (2)	C13—H13A	0.9300
C3—H3A	0.9300	C14—C15	1.380 (2)
C4—C5	1.383 (2)	C14—H14A	0.9300
C4—H4A	0.9300	C15—H15A	0.9300
C5—C6	1.383 (2)
C8—N1—C9	121.74 (10)	O2—C8—N1	122.59 (11)
C8—N1—H1N1	115.6 (10)	O2—C8—C7	118.81 (11)
C9—N1—H1N1	122.6 (10)	N1—C8—C7	117.88 (10)
C2—C1—C6	119.74 (16)	O3—C9—N1	119.05 (11)
C2—C1—H1A	120.1	O3—C9—C10	122.50 (10)
C6—C1—H1A	120.1	N1—C9—C10	118.44 (10)
C3—C2—C1	120.14 (15)	C15—C10—C11	119.20 (12)
C3—C2—H2A	119.9	C15—C10—C9	116.69 (10)
C1—C2—H2A	119.9	C11—C10—C9	124.09 (11)
C2—C3—C4	120.52 (15)	C12—C11—C10	119.85 (12)
C2—C3—H3A	119.7	C12—C11—H11A	120.1
C4—C3—H3A	119.7	C10—C11—H11A	120.1
C3—C4—C5	119.75 (16)	C13—C12—C11	120.44 (13)
C3—C4—H4A	120.1	C13—C12—H12A	119.8
C5—C4—H4A	120.1	C11—C12—H12A	119.8
C4—C5—C6	120.10 (14)	C12—C13—C14	120.04 (14)
C4—C5—H5A	119.9	C12—C13—H13A	120.0
C6—C5—H5A	119.9	C14—C13—H13A	120.0
C5—C6—C1	119.73 (13)	C13—C14—C15	119.87 (13)
C5—C6—C7	121.43 (11)	C13—C14—H14A	120.1
C1—C6—C7	118.81 (13)	C15—C14—H14A	120.1
O1—C7—C6	124.36 (11)	C14—C15—C10	120.59 (13)
O1—C7—C8	115.00 (11)	C14—C15—H15A	119.7
C6—C7—C8	120.35 (11)	C10—C15—H15A	119.7
C6—C1—C2—C3	−0.8 (2)	O1—C7—C8—N1	71.15 (15)
C1—C2—C3—C4	−0.2 (3)	C6—C7—C8—N1	−114.71 (13)
C2—C3—C4—C5	0.9 (2)	C8—N1—C9—O3	13.09 (19)
C3—C4—C5—C6	−0.7 (2)	C8—N1—C9—C10	−165.59 (12)
C4—C5—C6—C1	−0.2 (2)	O3—C9—C10—C15	1.00 (19)
C4—C5—C6—C7	177.86 (13)	N1—C9—C10—C15	179.64 (12)
C2—C1—C6—C5	1.0 (2)	O3—C9—C10—C11	−177.49 (13)
C2—C1—C6—C7	−177.13 (13)	N1—C9—C10—C11	1.15 (19)
C5—C6—C7—O1	174.79 (12)	C15—C10—C11—C12	0.8 (2)
C1—C6—C7—O1	−7.10 (19)	C9—C10—C11—C12	179.20 (13)
C5—C6—C7—C8	1.23 (18)	C10—C11—C12—C13	−0.6 (2)
C1—C6—C7—C8	179.33 (11)	C11—C12—C13—C14	0.0 (3)
C9—N1—C8—O2	−167.27 (13)	C12—C13—C14—C15	0.5 (3)
C9—N1—C8—C7	22.58 (18)	C13—C14—C15—C10	−0.4 (3)
O1—C7—C8—O2	−99.38 (15)	C11—C10—C15—C14	−0.3 (2)
C6—C7—C8—O2	74.76 (16)	C9—C10—C15—C14	−178.82 (14)

Cg1 is the centroid of the C1–C6 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O2i	0.879 (16)	2.107 (16)	2.9765 (14)	170.0 (15)
C11—H11A···O2i	0.93	2.51	3.4080 (18)	162
C14—H14A···Cg1ii	0.93	2.86	3.6592 (18)	145

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O2i	0.879 (16)	2.107 (16)	2.9765 (14)	170.0 (15)
C11—H11A⋯O2i	0.93	2.51	3.4080 (18)	162
C14—H14A⋯Cg1ii	0.93	2.86	3.6592 (18)	145

Symmetry codes: (i) ; (ii) .