N-Benzoyl-N'-phenyl-urea.

In the title compound, C(14)H(12)N(2)O(2), the mol-ecular conformation is determined by a strong intra-molecular N-H⋯O=C hydrogen bond. In the crystal, pairs of mol-ecules are connected by inter-molecular N-H⋯O=C hydrogen bonds, forming centrosymmetric dimers. No specific inter-actions between dimers could be found.

Related literature

For related structures, see: Bart et al. (1989 ▶); Zhong et al. (1998 ▶); Moon et al. (2002 ▶), Yamin & Mardi (2003 ▶); Chen et al. (2004 ▶); Su (2005 ▶); Yan et al. (2007 ▶, 2008 ▶); Liu et al. (2008 ▶, 2008a ▶,b ▶). For graph-set notation, see: Etter (1990 ▶). The title compound was obtained as a byproduct during the synthesis of a copper(I) complex with N-benzoyl-N′-phenyl­thio­urea prepared according to Frank & Smith (1948 ▶).

Experimental

Crystal data

C14H12N2O2

M = 240.26

Monoclinic,

a = 15.5641 (8) Å

b = 4.6564 (3) Å

c = 21.1029 (15) Å

β = 128.716 (4)°

V = 1193.31 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 150 K

0.54 × 0.10 × 0.09 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire2 (large Be window) detector

Absorption correction: analytical [CrysAlis PRO (Oxford Diffraction, 2009 ▶); analytical numeric absorption correction using a multi-faceted crystal model based on expressions derived by Clark & Reid (1995 ▶)] T min = 0.971, T max = 0.993

4425 measured reflections

2221 independent reflections

1575 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.098

S = 0.94

2221 reflections

211 parameters

Only H-atom coordinates refined

Δρmax = 0.22 e Å−3

Δρmin = −0.14 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); 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, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810001807/im2175sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810001807/im2175Isup2.hkl

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

C14H12N2O2	F(000) = 504
Mr = 240.26	Dx = 1.337 Mg m−3
Monoclinic, P21/c	Melting point: 482(2) K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 15.5641 (8) Å	Cell parameters from 2481 reflections
b = 4.6564 (3) Å	θ = 2.5–28.4°
c = 21.1029 (15) Å	µ = 0.09 mm−1
β = 128.716 (4)°	T = 150 K
V = 1193.31 (15) Å3	Needle, colourless
Z = 4	0.54 × 0.10 × 0.09 mm

Oxford Diffraction Xcalibur diffractometer with a Sapphire2 (large Be window) detector	2221 independent reflections
Radiation source: Mo Kα radiation	1575 reflections with I > 2σ(I)
graphite	Rint = 0.022
Detector resolution: 8.1883 pixels mm-1	θmax = 25.5°, θmin = 2.5°
ω scans	h = −18→9
Absorption correction: analytical [CrysAlis PRO (Oxford Diffraction, 2009); analytical numeric absorption correction using a multi-faceted crystal model based on expressions derived by Clark & Reid (1995)]	k = −3→5
Tmin = 0.971, Tmax = 0.993	l = −21→25
4425 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)] = 0.039	Hydrogen site location: difference Fourier map
wR(F2) = 0.098	Only H-atom coordinates refined
S = 0.94	w = 1/[σ2(Fo2) + (0.0656P)2] where P = (Fo2 + 2Fc2)/3
2221 reflections	(Δ/σ)max < 0.001
211 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.14 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 > 2σ(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	0.58625 (7)	0.6582 (2)	−0.00745 (6)	0.0384 (3)
O2	0.82393 (7)	0.2951 (2)	0.21526 (6)	0.0396 (3)
N1	0.77093 (9)	0.6517 (3)	0.09887 (7)	0.0295 (3)
N2	0.64890 (9)	0.3566 (3)	0.09771 (7)	0.0284 (3)
C1	0.66640 (10)	0.5660 (3)	0.05886 (8)	0.0274 (3)
C2	0.72519 (10)	0.2381 (3)	0.17319 (8)	0.0282 (3)
C11	0.81196 (11)	0.8530 (3)	0.07373 (9)	0.0297 (4)
C12	0.74750 (12)	0.9966 (3)	−0.00011 (9)	0.0330 (4)
C13	0.79673 (13)	1.1897 (4)	−0.01876 (10)	0.0393 (4)
C14	0.90876 (14)	1.2390 (4)	0.03479 (11)	0.0469 (5)
C15	0.97228 (13)	1.0949 (4)	0.10784 (12)	0.0516 (5)
C16	0.92476 (12)	0.9038 (4)	0.12780 (11)	0.0411 (4)
C21	0.68355 (10)	0.0351 (3)	0.20329 (8)	0.0275 (3)
C22	0.75435 (12)	−0.0253 (3)	0.28626 (9)	0.0336 (4)
C23	0.72257 (13)	−0.2128 (4)	0.31894 (10)	0.0389 (4)
C24	0.61969 (13)	−0.3423 (4)	0.26921 (10)	0.0390 (4)
C25	0.54898 (12)	−0.2851 (3)	0.18661 (10)	0.0368 (4)
C26	0.58046 (11)	−0.0960 (3)	0.15362 (9)	0.0316 (4)
H1	0.8205 (12)	0.559 (3)	0.1480 (10)	0.039 (4)*
H13	0.7502 (12)	1.291 (4)	−0.0711 (10)	0.041 (4)*
H12	0.6663 (12)	0.961 (3)	−0.0395 (8)	0.032 (4)*
H2	0.5745 (13)	0.328 (3)	0.0717 (9)	0.041 (4)*
H23	0.7751 (12)	−0.257 (3)	0.3782 (10)	0.040 (4)*
H26	0.5289 (12)	−0.059 (3)	0.0951 (9)	0.032 (4)*
H22	0.8256 (13)	0.077 (4)	0.3210 (9)	0.044 (4)*
H25	0.4762 (13)	−0.375 (3)	0.1504 (9)	0.043 (4)*
H24	0.5963 (12)	−0.477 (4)	0.2916 (9)	0.043 (4)*
H14	0.9397 (13)	1.385 (4)	0.0187 (10)	0.056 (5)*
H15	1.0520 (15)	1.117 (4)	0.1465 (10)	0.060 (5)*
H16	0.9654 (14)	0.800 (4)	0.1778 (11)	0.055 (5)*

	U11	U22	U33	U12	U13	U23
O1	0.0223 (5)	0.0518 (7)	0.0288 (6)	−0.0014 (4)	0.0100 (5)	0.0106 (5)
O2	0.0231 (5)	0.0527 (7)	0.0304 (6)	−0.0018 (5)	0.0107 (5)	0.0068 (5)
N1	0.0205 (6)	0.0363 (7)	0.0235 (6)	−0.0025 (5)	0.0097 (5)	0.0026 (6)
N2	0.0199 (6)	0.0351 (7)	0.0239 (6)	−0.0017 (5)	0.0106 (5)	0.0007 (6)
C1	0.0234 (7)	0.0333 (8)	0.0226 (7)	−0.0020 (6)	0.0130 (6)	−0.0018 (7)
C2	0.0237 (7)	0.0320 (8)	0.0243 (7)	0.0018 (6)	0.0128 (6)	−0.0015 (7)
C11	0.0275 (7)	0.0316 (8)	0.0297 (8)	−0.0041 (6)	0.0178 (6)	−0.0048 (7)
C12	0.0308 (8)	0.0373 (9)	0.0289 (8)	−0.0040 (6)	0.0178 (7)	−0.0030 (7)
C13	0.0443 (9)	0.0417 (10)	0.0360 (9)	−0.0046 (7)	0.0270 (8)	−0.0006 (8)
C14	0.0473 (10)	0.0458 (11)	0.0562 (11)	−0.0118 (8)	0.0366 (9)	−0.0009 (9)
C15	0.0303 (9)	0.0560 (12)	0.0579 (12)	−0.0089 (8)	0.0223 (9)	0.0049 (10)
C16	0.0273 (8)	0.0438 (10)	0.0413 (10)	−0.0041 (7)	0.0162 (7)	0.0051 (9)
C21	0.0279 (7)	0.0267 (8)	0.0276 (7)	0.0058 (6)	0.0173 (6)	0.0011 (7)
C22	0.0333 (8)	0.0339 (9)	0.0286 (8)	0.0037 (6)	0.0169 (7)	0.0011 (7)
C23	0.0441 (9)	0.0422 (10)	0.0296 (8)	0.0067 (7)	0.0227 (7)	0.0047 (8)
C24	0.0471 (9)	0.0367 (9)	0.0444 (9)	0.0052 (7)	0.0340 (8)	0.0080 (8)
C25	0.0357 (8)	0.0356 (9)	0.0425 (9)	0.0002 (7)	0.0261 (8)	0.0015 (8)
C26	0.0282 (7)	0.0355 (9)	0.0286 (8)	0.0033 (6)	0.0165 (7)	0.0026 (7)

O1—C1	1.2308 (16)	C14—H14	1.007 (19)
O2—C2	1.2304 (15)	C15—C16	1.381 (2)
N1—C1	1.3419 (16)	C15—H15	0.975 (18)
N1—C11	1.4114 (18)	C16—H16	0.956 (19)
N1—H1	0.926 (16)	C21—C26	1.394 (2)
N2—C2	1.3731 (18)	C21—C22	1.3950 (19)
N2—C1	1.4058 (18)	C22—C23	1.382 (2)
N2—H2	0.930 (15)	C22—H22	0.988 (16)
C2—C21	1.494 (2)	C23—C24	1.388 (2)
C11—C12	1.388 (2)	C23—H23	0.998 (16)
C11—C16	1.3907 (19)	C24—C25	1.386 (2)
C12—C13	1.388 (2)	C24—H24	0.983 (17)
C12—H12	1.001 (14)	C25—C26	1.388 (2)
C13—C14	1.380 (2)	C25—H25	0.980 (16)
C13—H13	0.984 (17)	C26—H26	0.979 (15)
C14—C15	1.378 (3)
C1—N1—C11	128.07 (12)	C14—C15—C16	120.59 (15)
C1—N1—H1	113.5 (9)	C14—C15—H15	122.2 (10)
C11—N1—H1	118.4 (9)	C16—C15—H15	117.2 (11)
C2—N2—C1	127.79 (11)	C15—C16—C11	120.10 (16)
C2—N2—H2	118.7 (9)	C15—C16—H16	123.5 (10)
C1—N2—H2	112.3 (10)	C11—C16—H16	116.4 (10)
O1—C1—N1	125.41 (14)	C26—C21—C22	119.31 (14)
O1—C1—N2	118.47 (11)	C26—C21—C2	123.99 (13)
N1—C1—N2	116.12 (12)	C22—C21—C2	116.69 (13)
O2—C2—N2	122.27 (13)	C23—C22—C21	120.37 (14)
O2—C2—C21	120.53 (12)	C23—C22—H22	121.3 (9)
N2—C2—C21	117.20 (12)	C21—C22—H22	118.3 (9)
C12—C11—C16	119.63 (14)	C22—C23—C24	120.06 (15)
C12—C11—N1	124.25 (12)	C22—C23—H23	119.3 (9)
C16—C11—N1	116.12 (13)	C24—C23—H23	120.7 (9)
C11—C12—C13	119.38 (14)	C25—C24—C23	120.03 (15)
C11—C12—H12	120.2 (8)	C25—C24—H24	119.1 (9)
C13—C12—H12	120.4 (8)	C23—C24—H24	120.9 (9)
C14—C13—C12	120.96 (16)	C24—C25—C26	120.07 (15)
C14—C13—H13	120.3 (9)	C24—C25—H25	121.3 (9)
C12—C13—H13	118.7 (9)	C26—C25—H25	118.6 (9)
C15—C14—C13	119.33 (16)	C25—C26—C21	120.16 (14)
C15—C14—H14	123.1 (10)	C25—C26—H26	118.5 (9)
C13—C14—H14	117.5 (10)	C21—C26—H26	121.4 (9)
N1—C1—N2—C2	3.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.93 (2)	1.85 (2)	2.634 (2)	140 (1)
N2—H2···O1i	0.93 (2)	1.97 (2)	2.882 (1)	169 (1)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2	0.93 (2)	1.85 (2)	2.634 (2)	140 (1)
N2—H2⋯O1i	0.93 (2)	1.97 (2)	2.882 (1)	169 (1)

Symmetry code: (i) .