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Volume 69 
Part 12 
Pages o1726-o1727  
December 2013  

Received 20 October 2013
Accepted 28 October 2013
Online 6 November 2013

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.003 Å
R = 0.046
wR = 0.130
Data-to-parameter ratio = 14.5
Details
Open access

N-(1,5-Dimethyl-3-oxo-2-phenyl-2,3-di­hydro-1H-pyrazol-4-yl)-2-phenyl­acetamide

aDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India,bDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA, and cDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India
Correspondence e-mail: jjasinski@keene.edu

The title compound, C19H19N3O2, crystallizes with two independent mol­ecules (A and B) in the asymmetric unit. In mol­ecule A, the pyrazole ring adopts a slightly disordered half-chair conformation while in B it is planar [r.m.s. deviation = 0.0386 (15) Å]. The dihedral angle between the mean planes of the two phenyl rings is 56.2 (8) in A and 38.2 (3)° in B. The N-phenyl substituent on the pyrazole ring is twisted by 46.5 (2) in A and 58.6 (4)° in B while the extended phenyl ring is twisted by 82.2 (8) in A and 87.5 (9)° in B. The mean plane of the amide group forms an angle of 74.8 (3) in A and 67.7 (1)° in B with respect to the phenyl ring. In addition, the amide group is rotated by 51.4 (1) in A and 53.6 (2)° in B from the the mean plane of the pyrazole ring. In the crystal, the two molecules are linked via N-H...O hydrogen bonds, supported by weak C-H...O inter­actions, forming dimers enclosing an R22(10) ring motif. The dimers are linked via C-H...O inter­actions, forming a three-dimensional structure.

Related literature

For the structural similarity of N-substituted 2-aryl­acetamides to the lateral chain of natural benzyl­penicillin, see: Mijin et al. (2008[Mijin, D. Z., Prascevic, M. & Petrovic, S. D. (2008). J. Serb. Chem. Soc. 73, 945-950.]). For the coordination abilities of amides, 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 pharmaceutical, insecticidal and non-linear properties of pyrazoles, see: Chandrakantha et al. (2013[Chandrakantha, B., Isloor, A. M., Sridharan, K., Philip, R., Shetty, P. & Padaki, M. (2013). Arabian J. Chem. 6, 97-102.]); Cheng et al. (2008[Cheng, J. L., Wei, F. L., Zhu, L., Zhao, J. H. & Zhu, G. N. (2008). Chin. J. Org. Chem. 28, 622-627.]); Hatton et al. (1993[Hatton, L. R., Buntain, I. G., Hawkins, D. W., Parnell, E. W. & Pearson, C. J. (1993). US Patent 5232940.]); Liu et al. (2010[Liu, Y. Y., Shi, H., Li, Y. F. & Zhu, H. J. (2010). J. Heterocycl. Chem. 47, 897-902.]). For related structures, 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.], 2012[Fun, H.-K., Quah, C. K., Nayak, P. S., Narayana, B. & Sarojini, B. K. (2012). Acta Cryst. E68, o2677.]); Butcher et al. (2013a[Butcher, R. J., Mahan, A., Nayak, P. S., Narayana, B. & Yathirajan, H. S. (2013a). Acta Cryst. E69, o46-o47.],b[Butcher, R. J., Mahan, A., Nayak, P. S., Narayana, B. & Yathirajan, H. S. (2013b). Acta Cryst. E69, o39.]). For puckering parameters, see Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). For standard bond lengths, 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
  • C19H19N3O2

  • Mr = 321.37

  • Triclinic, [P \overline 1]

  • a = 10.1258 (7) Å

  • b = 10.4671 (8) Å

  • c = 17.8888 (12) Å

  • [alpha] = 100.833 (6)°

  • [beta] = 92.527 (5)°

  • [gamma] = 116.812 (7)°

  • V = 1643.9 (2) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 0.69 mm-1

  • T = 173 K

  • 0.48 × 0.32 × 0.26 mm

Data collection
  • Agilent Xcalibur (Eos, Gemini) diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]) Tmin = 0.876, Tmax = 1.000

  • 10216 measured reflections

  • 6333 independent reflections

  • 5485 reflections with I > 2[sigma](I)

  • Rint = 0.037

Refinement
  • R[F2 > 2[sigma](F2)] = 0.046

  • wR(F2) = 0.130

  • S = 1.04

  • 6333 reflections

  • 438 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.30 e Å-3

  • [Delta][rho]min = -0.23 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1A-H1A...O2B 0.86 1.97 2.8292 (16) 173
C14A-H14A...O1Ai 0.93 2.55 3.454 (2) 165
N1B-H1B...O2A 0.86 1.98 2.8115 (16) 163
C2B-H2BA...O1Bii 0.97 2.55 3.4239 (19) 150
C4B-H4B...O1Bii 0.93 2.72 3.487 (2) 141
C8B-H8B...O2A 0.93 2.57 3.404 (2) 150
C14B-H14B...O1Aiii 0.93 2.70 3.398 (2) 132
Symmetry codes: (i) -x+1, -y+1, -z; (ii) -x+1, -y+1, -z+1; (iii) x-1, y-1, z.

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007[Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790.]); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]); software used to prepare material for publication: OLEX2.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG5356 ).


Acknowledgements

MK is grateful to CPEPA-UGC for the award of a JRF and thanks the University of Mysore for research facilities. JPJ acknowledges the NSF-MRI program (grant No. CHE-1039027) for funds to purchase the X-ray diffractometer.

References

Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.
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.
Butcher, R. J., Mahan, A., Nayak, P. S., Narayana, B. & Yathirajan, H. S. (2013a). Acta Cryst. E69, o46-o47.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Butcher, R. J., Mahan, A., Nayak, P. S., Narayana, B. & Yathirajan, H. S. (2013b). Acta Cryst. E69, o39.  [CSD] [CrossRef] [IUCr Journals]
Chandrakantha, B., Isloor, A. M., Sridharan, K., Philip, R., Shetty, P. & Padaki, M. (2013). Arabian J. Chem. 6, 97-102.  [CrossRef] [ChemPort]
Cheng, J. L., Wei, F. L., Zhu, L., Zhao, J. H. & Zhu, G. N. (2008). Chin. J. Org. Chem. 28, 622-627.  [ChemPort]
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [Web of Science]
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Fun, H.-K., Quah, C. K., Narayana, B., Nayak, P. S. & Sarojini, B. K. (2011a). Acta Cryst. E67, o2926-o2927.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Fun, H.-K., Quah, C. K., Narayana, B., Nayak, P. S. & Sarojini, B. K. (2011b). Acta Cryst. E67, o2941-o2942.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Fun, H.-K., Quah, C. K., Nayak, P. S., Narayana, B. & Sarojini, B. K. (2012). Acta Cryst. E68, o2677.  [CSD] [CrossRef] [IUCr Journals]
Hatton, L. R., Buntain, I. G., Hawkins, D. W., Parnell, E. W. & Pearson, C. J. (1993). US Patent 5232940.
Liu, Y. Y., Shi, H., Li, Y. F. & Zhu, H. J. (2010). J. Heterocycl. Chem. 47, 897-902.  [CrossRef] [ChemPort]
Mijin, D. Z., Prascevic, M. & Petrovic, S. D. (2008). J. Serb. Chem. Soc. 73, 945-950.  [Web of Science] [CrossRef] [ChemPort]
Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Wu, W.-N., Cheng, F.-X., Yan, L. & Tang, N. (2008). J. Coord. Chem. 61, 2207-2215.  [Web of Science] [CrossRef] [ChemPort]
Wu, W.-N., Wang, Y., Zhang, A.-Y., Zhao, R.-Q. & Wang, Q.-F. (2010). Acta Cryst. E66, m288.  [CSD] [CrossRef] [IUCr Journals]


Acta Cryst (2013). E69, o1726-o1727   [ doi:10.1107/S1600536813029590 ]

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