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Volume 67 
Part 1 
Page o197  
January 2011  

Received 14 December 2010
Accepted 15 December 2010
Online 18 December 2010

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.002 Å
R = 0.044
wR = 0.124
Data-to-parameter ratio = 20.6
Details
Open access

N-(2-Oxo-2-phenylacetyl)benzamide

aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and bSchool of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, People's Republic of China
Correspondence e-mail: hkfun@usm.my

In the title compound, C15H11NO3, 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, intermolecular bifurcated acceptor N-H...O and C-H...O hydrogen bonds link inversion-related molecules into dimers incorporating R12(7) and R22(8) ring motifs. The crystal structure is further stabilized by weak intermolecular C-H...[pi] interactions.

Related literature

For general background to and applications of the title benzamide compound, see: Haffner & Ulrich (2010[Haffner, C. D. & Ulrich, J. (2010). Bioorg. Med. Chem. Lett. 20, 6989-6992.]); Lavanya & Rao (2010[Lavanya, P. & Rao, C. V. (2010). J. Chem. Pharm. Res. 2, 25-32.]); Magarl et al. (2010[Magarl, D. D., Tapas, A. R. & Ambre, P. K. (2010). Pharma Chem. 2, 142-147.]). For graph-set descriptions of hydrogen-bond ring motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). For related benzamide structures, see: Jotani et al. (2010[Jotani, M. M., Baldaniya, B. B. & Tiekink, E. R. T. (2010). Acta Cryst. E66, o778.]); Fu et al. (1998[Fu, T. Y., Scheffer, J. R. & Trotter, J. (1998). Acta Cryst. C54, 101-102.]); Gallagher et al. (2009[Gallagher, J. F., Donnelly, K. & Lough, A. J. (2009). Acta Cryst. E65, o486-o487.]). For related diketone structures, see: Cheah et al. (2008[Cheah, W. C., Black, D. S., Goh, W. K. & Kumar, N. (2008). Tetrahedron Lett. 49, 2965-2968.]); Hartung et al. (2004[Hartung, J., Spehar, K., Svoboda, I. & Fuess, H. (2004). Acta Cryst. E60, o750-o751.]). For standard bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C15H11NO3

  • Mr = 253.25

  • Monoclinic, P 21 /c

  • a = 5.7215 (1) Å

  • b = 10.7241 (1) Å

  • c = 20.6710 (3) Å

  • [beta] = 98.255 (1)°

  • V = 1255.19 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.967, Tmax = 0.975

  • 13904 measured reflections

  • 3624 independent reflections

  • 2549 reflections with I > 2[sigma](I)

  • Rint = 0.025

Refinement
  • R[F2 > 2[sigma](F2)] = 0.044

  • wR(F2) = 0.124

  • S = 1.03

  • 3624 reflections

  • 176 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.22 e Å-3

  • [Delta][rho]min = -0.19 e Å-3

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) -x+1, -y+1, -z+2; (ii) -x, -y, -z+2.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL 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: LH5192 ).


Acknowledgements

HKF and JHG thank Universiti Sains Malaysia (USM) for a Research University Grant (No. 1001/PFIZIK/811160). Financial support from the Fok Ying Tung Education Foundation (114012) is also acknowledged.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cheah, W. C., Black, D. S., Goh, W. K. & Kumar, N. (2008). Tetrahedron Lett. 49, 2965-2968.  [CrossRef] [ChemPort]
Fu, T. Y., Scheffer, J. R. & Trotter, J. (1998). Acta Cryst. C54, 101-102.  [CrossRef] [details]
Gallagher, J. F., Donnelly, K. & Lough, A. J. (2009). Acta Cryst. E65, o486-o487.  [CSD] [CrossRef] [details]
Haffner, C. D. & Ulrich, J. (2010). Bioorg. Med. Chem. Lett. 20, 6989-6992.  [CrossRef] [ChemPort] [PubMed]
Hartung, J., Spehar, K., Svoboda, I. & Fuess, H. (2004). Acta Cryst. E60, o750-o751.  [CSD] [CrossRef] [details]
Jotani, M. M., Baldaniya, B. B. & Tiekink, E. R. T. (2010). Acta Cryst. E66, o778.  [CrossRef] [details]
Lavanya, P. & Rao, C. V. (2010). J. Chem. Pharm. Res. 2, 25-32.  [ChemPort]
Magarl, D. D., Tapas, A. R. & Ambre, P. K. (2010). Pharma Chem. 2, 142-147.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2011). E67, o197  [ doi:10.1107/S160053681005258X ]

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