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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 [sigma](C-C) = 0.003 Å
R = 0.039
wR = 0.098
Data-to-parameter ratio = 10.5
Details
Open access

N-Benzoyl-N'-phenylurea

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-H...O=C hydrogen bond. In the crystal, pairs of molecules are connected by intermolecular N-H...O=C hydrogen bonds, forming centrosymmetric dimers. No specific interactions between dimers could be found.

Related literature

For related structures, see: Bart et al. (1989[Bart, J. C. J., Calcaterra, M., Cavigiolo, W. & Massardo, P. (1989). J. Crystallogr. Spectrosc. Res. 19, 99-108.]); Zhong et al. (1998[Zhong, L., Xuhong, Q., Zhixiang, Z., Zongxiang, X. & Jie, S. (1998). J. Chem. Res. pp. 478-479.]); Moon et al. (2002[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.]), Yamin & Mardi (2003[Yamin, B. M. & Mardi, A. S. (2003). Acta Cryst. E59, o399-o400.]); Chen et al. (2004[Chen, L., Song, H.-B., Wang, Q.-M., Huang, R.-Q., Shang, J. & Mao, C.-H. (2004). Acta Cryst. E60, o1865-o1867.]); Su (2005[Su, B.-Q. (2005). Acta Cryst. E61, o3492-o3494.]); Yan et al. (2007[Yan, S.-J., Yan, Y.-Y., Li, Y.-M., Xie, M.-J. & Lin, J. (2007). Acta Cryst. E63, o2944.], 2008[Yan, S.-J., Huang, C., Li, Y.-M., Yan, Y.-Y. & Lin, J. (2008). Acta Cryst. E64, o2102.]); Liu et al. (2008[Liu, Y., Li, F. & Li, Y. (2008). Acta Cryst. E64, o1756.], 2008a[Liu, Y.-H., Li, F.-S., Li, Y., Yu, D.-S. & Lu, C. (2008a). Acta Cryst. E64, o1729.],b[Liu, Y., Li, F., Yin, L. & Yu, D. (2008b). Acta Cryst. E64, o1218.]). For graph-set notation, see: Etter (1990[Etter, M. C. (1990). Acc. Chem. Res. 23, 120-126.]). 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[Frank, R. L. & Smith, P. V. (1948). Org. Synth. 28, 89-91.]).

[Scheme 1]

Experimental

Crystal data
  • C14H12N2O2

  • Mr = 240.26

  • Monoclinic, P 21 /c

  • a = 15.5641 (8) Å

  • b = 4.6564 (3) Å

  • c = 21.1029 (15) Å

  • [beta] = 128.716 (4)°

  • V = 1193.31 (15) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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[Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897.])] Tmin = 0.971, Tmax = 0.993

  • 4425 measured reflections

  • 2221 independent reflections

  • 1575 reflections with I > 2[sigma](I)

  • Rint = 0.022

Refinement
  • R[F2 > 2[sigma](F2)] = 0.039

  • wR(F2) = 0.098

  • S = 0.94

  • 2221 reflections

  • 211 parameters

  • Only H-atom coordinates refined

  • [Delta][rho]max = 0.22 e Å-3

  • [Delta][rho]min = -0.14 e Å-3

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) -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[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


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.  [CrossRef] [ChemPort] [ISI]
Chen, L., Song, H.-B., Wang, Q.-M., Huang, R.-Q., Shang, J. & Mao, C.-H. (2004). Acta Cryst. E60, o1865-o1867.  [CSD] [CrossRef] [details]
Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897.  [CrossRef] [details]
Etter, M. C. (1990). Acc. Chem. Res. 23, 120-126.  [CrossRef] [ChemPort] [ISI]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [CrossRef] [ChemPort] [details]
Frank, R. L. & Smith, P. V. (1948). Org. Synth. 28, 89-91.  [ChemPort]
Liu, Y., Li, F. & Li, Y. (2008). Acta Cryst. E64, o1756.  [CSD] [CrossRef] [details]
Liu, Y.-H., Li, F.-S., Li, Y., Yu, D.-S. & Lu, C. (2008a). Acta Cryst. E64, o1729.  [CSD] [CrossRef] [details]
Liu, Y., Li, F., Yin, L. & Yu, D. (2008b). Acta Cryst. E64, o1218.  [CSD] [CrossRef] [details]
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.  [ChemPort]
Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Su, B.-Q. (2005). Acta Cryst. E61, o3492-o3494.  [CSD] [CrossRef] [details]
Yamin, B. M. & Mardi, A. S. (2003). Acta Cryst. E59, o399-o400.  [CSD] [CrossRef] [details]
Yan, S.-J., Huang, C., Li, Y.-M., Yan, Y.-Y. & Lin, J. (2008). Acta Cryst. E64, o2102.  [CrossRef] [details]
Yan, S.-J., Yan, Y.-Y., Li, Y.-M., Xie, M.-J. & Lin, J. (2007). Acta Cryst. E63, o2944.  [CSD] [CrossRef] [details]
Zhong, L., Xuhong, Q., Zhixiang, Z., Zongxiang, X. & Jie, S. (1998). J. Chem. Res. pp. 478-479.  [CrossRef]


Acta Cryst (2010). E66, o414  [ doi:10.1107/S1600536810001807 ]

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