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Volume 69 
Part 1 
Pages o46-o47  
January 2013  

Received 2 December 2012
Accepted 3 December 2012
Online 8 December 2012

Key indicators
Single-crystal X-ray study
T = 123 K
Mean [sigma](C-C) = 0.004 Å
R = 0.062
wR = 0.185
Data-to-parameter ratio = 15.6
Details
Open access

2-(2,6-Dichlorophenyl)-N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)acetamide

aDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA,bLake Braddock Secondary School, 9200 Burke Lake Road, Burke, VA 22015, USA,cDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India, and dDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India
Correspondence e-mail: rbutcher99@yahoo.com

In the title compound, C19H17Cl2N3O2, the amide group is planar and, through N-H...O hydrogen bonding to an adjoining molecule, forms dimers of the R22(10) type. As a result of steric repulsion, the amide group is rotated with respect to both the dichlorophenyl and 2,3-dihydro-1H-pyrazol-4-yl rings, making dihedral angles of 71.63 (11) and 57.93 (10)°, respectively. The dihedral angle between the dichlorophenyl and 2,3-dihydro-1H-pyrazol-4-yl rings is 76.60 (10)° while that between the 2,3-dihydro-1H-pyrazol-4-yl and phenyl rings is 49.29 (7)°. The crystal structure also features weak C-H...O interactions.

Related literature

N-Substituted 2-arylacetamides are of interest because of their structural similarity to the lateral chain of natural benzylpenicillin, see: Mijin & Marinkovic (2006[Mijin, D. & Marinkovic, A. (2006). Synth. Commun. 36, 193-198.]); Mijin et al. (2008[Mijin, D. Z., Prascevic, M. & Petrovic, S. D. (2008). J. Serb. Chem. Soc. 73, 945-950.]). For amides as ligands, see: Wu et al. (2008[Wu, W.-N., Cheng, F.-X., Yan, L. & Tang, N. (2008). J. Coord. Chem. 61, 2207-2215.], 2010[Wu, W.-N., Wang, Y., Zhang, A.-Y., Zhao, R.-Q. & Wang, Q.-F. (2010). Acta Cryst. E66, m288.]). For the structures of acetamide derivatives, see: Fun et al. (2011a[Fun, H.-K., Quah, C. K., Narayana, B., Nayak, P. S. & Sarojini, B. K. (2011a). Acta Cryst. E67, o2926-o2927.],b[Fun, H.-K., Quah, C. K., Narayana, B., Nayak, P. S. & Sarojini, B. K. (2011b). Acta Cryst. E67, o2941-o2942.], 2012a[Fun, H.-K., Quah, C. K., Nayak, P. S., Narayana, B. & Sarojini, B. K. (2012a). Acta Cryst. E68, o2677.],b[Fun, H.-K., Shahani, T., Nayak, P. S., Narayana, B. & Sarojini, B. K. (2012b). Acta Cryst. E68, o519.]). For a description of the Cambridge Structural Database, see: Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]). 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
  • C19H17Cl2N3O2

  • Mr = 390.26

  • Monoclinic, C 2/c

  • a = 20.3442 (11) Å

  • b = 12.1080 (8) Å

  • c = 14.9500 (8) Å

  • [beta] = 93.837 (5)°

  • V = 3674.3 (4) Å3

  • Z = 8

  • Cu K[alpha] radiation

  • [mu] = 3.34 mm-1

  • T = 123 K

  • 0.60 × 0.55 × 0.24 mm

Data collection
  • Agilent Xcalibur (Ruby, Gemini) diffractometer

  • Absorption correction: analytical [CrysAlis PRO (Agilent, 2011[Agilent. (2011). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]) based on expressions derived by Clark & Reid (1995[Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897.])] Tmin = 0.276, Tmax = 0.560

  • 6894 measured reflections

  • 3692 independent reflections

  • 2836 reflections with I > 2[sigma](I)

  • Rint = 0.065

Refinement
  • R[F2 > 2[sigma](F2)] = 0.062

  • wR(F2) = 0.185

  • S = 1.05

  • 3692 reflections

  • 237 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.51 e Å-3

  • [Delta][rho]min = -0.62 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1A...O2i 0.88 1.99 2.845 (3) 164
C7-H7A...O2i 0.99 2.47 3.249 (3) 135
C12-H12A...O1ii 0.98 2.43 3.104 (3) 126
Symmetry codes: (i) [-x+1, y, -z+{\script{1\over 2}}]; (ii) [-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: CrysAlis PRO (Agilent, 2011[Agilent. (2011). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO (Agilent, 2011[Agilent. (2011). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]); 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG5277 ).


Acknowledgements

BN thanks the UGC for financial assistance through a BSR one-time grant for the purchase of chemicals. PSN thanks Mangalore University for research facilities and the DST-PURSE financial assistance. RJB acknowledges the NSF-MRI program (grant No. CHE-0619278) for funds to purchase the diffractometer.

References

Agilent. (2011). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.
Allen, F. H. (2002). Acta Cryst. B58, 380-388.  [ISI] [CrossRef] [details]
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897.  [CrossRef] [details]
Fun, H.-K., Quah, C. K., Narayana, B., Nayak, P. S. & Sarojini, B. K. (2011a). Acta Cryst. E67, o2926-o2927.  [CSD] [CrossRef] [details]
Fun, H.-K., Quah, C. K., Narayana, B., Nayak, P. S. & Sarojini, B. K. (2011b). Acta Cryst. E67, o2941-o2942.  [CSD] [CrossRef] [details]
Fun, H.-K., Quah, C. K., Nayak, P. S., Narayana, B. & Sarojini, B. K. (2012a). Acta Cryst. E68, o2677.  [CSD] [CrossRef] [details]
Fun, H.-K., Shahani, T., Nayak, P. S., Narayana, B. & Sarojini, B. K. (2012b). Acta Cryst. E68, o519.  [CSD] [CrossRef] [details]
Mijin, D. & Marinkovic, A. (2006). Synth. Commun. 36, 193-198.  [ISI] [CrossRef] [ChemPort]
Mijin, D. Z., Prascevic, M. & Petrovic, S. D. (2008). J. Serb. Chem. Soc. 73, 945-950.  [ISI] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Wu, W.-N., Cheng, F.-X., Yan, L. & Tang, N. (2008). J. Coord. Chem. 61, 2207-2215.  [ISI] [CrossRef] [ChemPort]
Wu, W.-N., Wang, Y., Zhang, A.-Y., Zhao, R.-Q. & Wang, Q.-F. (2010). Acta Cryst. E66, m288.  [CSD] [CrossRef] [details]


Acta Cryst (2013). E69, o46-o47   [ doi:10.1107/S160053681204963X ]

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