N-Benzoyl-N′-phenyl­urea

Okuniewski, A.; Chojnacki, J.; Becker, B.

doi:10.1107/S1600536810001807

Volume 66
Part 2
Page o414
February 2010

Received 8 January 2010
Accepted 14 January 2010
Online 20 January 2010

Key indicators
Single-crystal X-ray study
T = 150 K
Mean (C-C) = 0.003 Å
R = 0.039
wR = 0.098
Data-to-parameter ratio = 10.5
Details

N-Benzoyl-N'-phenylurea

Andrzej Okuniewski,^a Jaroslaw Chojnacki ^a and Barbara Becker ^a ^*

^aDepartment of Inorganic Chemistry, Gdansk University of Technology, Narutowicza 11/12, 80-233 Gdansk, Poland
Correspondence e-mail: barbara.becker@pg.gda.pl

In the title compound, C₁₄H₁₂N₂O₂, the molecular conformation is determined by a strong intramolecular N-HO=C hydrogen bond. In the crystal, pairs of molecules are connected by intermolecular N-HO=C hydrogen bonds, forming centrosymmetric dimers. No specific interactions 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_r = 240.26
Monoclinic, P 2₁ /c
a = 15.5641 (8) Å
b = 4.6564 (3) Å
c = 21.1029 (15) Å
= 128.716 (4)°
V = 1193.31 (15) Å³
Z = 4
Mo K radiation
= 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 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); 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 > 2(I)
R_int = 0.022

Refinement

R[F² > 2(F²)] = 0.039
wR(F²) = 0.098
S = 0.94
2221 reflections
211 parameters
Only H-atom coordinates refined
_max = 0.22 e Å^-3
_min = -0.14 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1O2	0.93 (2)	1.85 (2)	2.634 (2)	140 (1)
N2-H2O1ⁱ	0.93 (2)	1.97 (2)	2.882 (1)	169 (1)
Symmetry code: (i) -x+1, -y+1, -z.

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); 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).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IM2175 ).

References

Bart, J. C. J., Calcaterra, M., Cavigiolo, W. & Massardo, P. (1989). J. Crystallogr. Spectrosc. Res. 19, 99-108.
Chen, L., Song, H.-B., Wang, Q.-M., Huang, R.-Q., Shang, J. & Mao, C.-H. (2004). Acta Cryst. E60, o1865-o1867.
Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897.
Etter, M. C. (1990). Acc. Chem. Res. 23, 120-126.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Frank, R. L. & Smith, P. V. (1948). Org. Synth. 28, 89-91.
Liu, Y., Li, F. & Li, Y. (2008). Acta Cryst. E64, o1756.
Liu, Y.-H., Li, F.-S., Li, Y., Yu, D.-S. & Lu, C. (2008a). Acta Cryst. E64, o1729.
Liu, Y., Li, F., Yin, L. & Yu, D. (2008b). Acta Cryst. E64, o1218.
Moon, J. K., Kim, J.-H., Rhee, S., Kim, G., Yun, H., Chung, B.-J., Lee, S. & Lim, Y. (2002). Bull. Korean Chem. Soc. 23, 1545-1547.
Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Su, B.-Q. (2005). Acta Cryst. E61, o3492-o3494.
Yamin, B. M. & Mardi, A. S. (2003). Acta Cryst. E59, o399-o400.
Yan, S.-J., Huang, C., Li, Y.-M., Yan, Y.-Y. & Lin, J. (2008). Acta Cryst. E64, o2102.
Yan, S.-J., Yan, Y.-Y., Li, Y.-M., Xie, M.-J. & Lin, J. (2007). Acta Cryst. E63, o2944.
Zhong, L., Xuhong, Q., Zhixiang, Z., Zongxiang, X. & Jie, S. (1998). J. Chem. Res. pp. 478-479.

organic compounds