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Volume 65 
Part 3 
Page o510  
March 2009  

Received 3 February 2009
Accepted 5 February 2009
Online 11 February 2009

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Key indicators
Single-crystal X-ray study
T = 120 K
Mean [sigma](C-C) = 0.003 Å
R = 0.039
wR = 0.105
Data-to-parameter ratio = 15.7
Details
Open access

4-[(2-Benzoyl-4-chlorophenyl)diazenyl]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one

Zaker Bahreni,a Hossein Rahmania and Seik Weng Ngb*

aInstitute of Chemical Industries, Iranian Research Organization for Science and Technology, PO Box 15815-358, Tehran, Iran, and bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
Correspondence e-mail: seikweng@um.edu.my

In the title compound, C23H17ClN4O2, the amino H atom forms an intramolecular hydrogen bond to the exocyclic carbonyl O atom as well as to the O atom of the benzoyl group.

Related literature

For the crystal structure of 1-phenyl-3-methyl-4-(4'-chlorophenyazo)-pyrazol-5-one, whose amino H atom is intramolecularly hydrogen-bonded to the carbonyl O atom, see: Golinski et al. (1983[Golinski, B., Reck, G. & Kutschabsky, L. (1983). Z. Kristallogr. 158, 271-278.]).

[Scheme 1]

Experimental

Crystal data

  • C23H17ClN4O2

  • Mr = 416.86

  • Monoclinic, C 2/c

  • a = 25.800 (3) Å

  • b = 12.124 (1) Å

  • c = 13.966 (1) Å

  • [beta] = 119.179 (1)°

  • V = 3813.9 (7) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.23 mm-1

  • T = 120 (2) K

  • 0.35 × 0.25 × 0.10 mm
Data collection

  • Bruker SMART APEX diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.791, Tmax = 0.862 (expected range = 0.897-0.977)

  • 10753 measured reflections

  • 4346 independent reflections

  • 3309 reflections with I > 2[sigma](I)

  • Rint = 0.032
Refinement

  • R[F2 > 2[sigma](F2)] = 0.039

  • wR(F2) = 0.105

  • S = 1.00

  • 4346 reflections

  • 276 parameters

  • 1 restraint

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

  • [Delta][rho]max = 0.30 e Å-3

  • [Delta][rho]min = -0.30 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N4-H4...O1 0.89 (1) 2.06 (2) 2.755 (2) 135 (2)
N4-H4...O2 0.89 (1) 2.05 (2) 2.698 (2) 130 (2)

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2009[Westrip, S. P. (2009). publCIF. In preparation.]).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2371 ).

Acknowledgements

We thank the Iranian Research Organization for Science and Technology and the University of Malaya for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.  [CrossRef] [ChemPort]
Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Golinski, B., Reck, G. & Kutschabsky, L. (1983). Z. Kristallogr. 158, 271-278.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Westrip, S. P. (2009). publCIF. In preparation.

Acta Cryst (2009). E65, o510  [ doi:10.1107/S1600536809004243 ]

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