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Volume 69 
Part 2 
Page o182  
February 2013  

Received 16 December 2012
Accepted 22 December 2012
Online 4 January 2013

Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.004 Å
Disorder in main residue
R = 0.045
wR = 0.135
Data-to-parameter ratio = 12.4
Details
Open access

Diethyl [(2-chloroanilino)(1,3-diphenyl-1H-pyrazol-4-yl)methyl]phosphonate

aDepartment of Physics, Presidency College (Autonomous), Chennai 600 005, India, and bOrganic Chemistry Laboratory, CLRI, Chennai, Tamilnadu, India
Correspondence e-mail: aravindhanpresidency@gmail.com

In the title compound, C26H27ClN3O3P, the mean plane of the central pyrazole ring forms a dihedral angle of 71.37 (14)° with the chlorophenyl ring. In the crystal, molecules are linked by pairs of N-H...O hydrogen bonds, forming inversion dimers with R22(10) ring motifs. The 3-phenyl ring is disordered with four C atoms occupying two sets of sites with an occupancy ratio of 0.748 (4):0.252 (4).

Related literature

For information on pyrazole derivatives, see: Sullivan et al. (2006[Sullivan, T. J., Truglio, J. J., Boyne, M. E., Novichenok, P., Zhang, X., Stratton, C. F., Li, H.-J., Kaur, T., Amin, A., Johnson, F., Slayden, R. A., Kisker, C. & Tonge, P. J. (2006). ACS Chem. Biol. 1, 43-53.]); Patel et al. (2010[Patel, C. K., Rami, C. S., Panigrahi, B. & Patel, C. N. (2010). J. Chem. Pharm. Res. 2, 73-78.]). For related structures, see: Saeed et al. (2009[Saeed, A., Hussain, S. & Bolte, M. (2009). Acta Cryst. E65, o1231.]); Suresh et al. (2012[Suresh, G., Sabari, V., Nandakumar, A., Perumal, P. T. & Aravindhan, S. (2012). Acta Cryst. E68, o1554.]). For hydrogen-bond 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.]).

[Scheme 1]

Experimental

Crystal data
  • C26H27ClN3O3P

  • Mr = 495.93

  • Monoclinic, P 21 /c

  • a = 11.2379 (3) Å

  • b = 23.7075 (6) Å

  • c = 9.4570 (2) Å

  • [beta] = 90.809 (1)°

  • V = 2519.31 (11) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.25 mm-1

  • T = 298 K

  • 0.25 × 0.20 × 0.18 mm

Data collection
  • Bruker APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.941, Tmax = 0.957

  • 14995 measured reflections

  • 4289 independent reflections

  • 3322 reflections with I > 2[sigma](I)

  • Rint = 0.020

Refinement
  • R[F2 > 2[sigma](F2)] = 0.045

  • wR(F2) = 0.135

  • S = 1.05

  • 4289 reflections

  • 346 parameters

  • 99 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.35 e Å-3

  • [Delta][rho]min = -0.29 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N3-H3A...O1i 0.86 2.37 3.199 (3) 163
Symmetry code: (i) -x, -y+1, -z.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. 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: ORTEP-3 (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXL97 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: SU2545 ).


Acknowledgements

GS and SA thank the UGC, India, for financial support. GS thanks the SAIF, IIT-Madras, for the instrumentation facility.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Patel, C. K., Rami, C. S., Panigrahi, B. & Patel, C. N. (2010). J. Chem. Pharm. Res. 2, 73-78.  [ChemPort]
Saeed, A., Hussain, S. & Bolte, M. (2009). Acta Cryst. E65, o1231.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Sullivan, T. J., Truglio, J. J., Boyne, M. E., Novichenok, P., Zhang, X., Stratton, C. F., Li, H.-J., Kaur, T., Amin, A., Johnson, F., Slayden, R. A., Kisker, C. & Tonge, P. J. (2006). ACS Chem. Biol. 1, 43-53.  [CrossRef] [PubMed] [ChemPort]
Suresh, G., Sabari, V., Nandakumar, A., Perumal, P. T. & Aravindhan, S. (2012). Acta Cryst. E68, o1554.  [CSD] [CrossRef] [details]


Acta Cryst (2013). E69, o182  [ doi:10.1107/S1600536812051719 ]

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