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

Mahan, A.; Butcher, R.J.; Nayak, P.S.; Narayana, B.; Yathirajan, H.S.

doi:10.1107/S1600536813002341

Volume 69
Part 3
Pages o402-o403
March 2013

Received 22 January 2013
Accepted 23 January 2013
Online 20 February 2013

Key indicators
Single-crystal X-ray study
T = 123 K
Mean (C-C) = 0.005 Å
R = 0.119
wR = 0.345
Data-to-parameter ratio = 38.8
Details

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

Aneeka Mahan,^a Ray J. Butcher,^b ^* Prakash S. Nayak,^c B. Narayana ^c and H. S. Yathirajan ^d

^aLake Braddock Secondary School, 9200 Burke Lake Road, Burke, VA 22015, USA,^bDepartment of Chemistry, Howard University, 525 College Street NW, Washington DC 20059, 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, there are three molecules (A, B and C) in the asymmetric unit and each differs in the conformation adopted. 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 44.5 (2) and 56.2 (2)°, respectively in A, 51.1 (2) and 54.1 (2)° in B, and 53.8 (2) and 54.6 (2)° in C. The dihedral angles between the dichlorophenyl and 2,3-dihydro-1H-pyrazol-4-yl rings are 54.8 (2), 76.2 (2) and 77.5 (2)° in molecules A, B and C, respectively, while the 2,3-dihydro-1H-pyrazol-4-yl and phenyl rings make dihedral angles of 45.3 (2), 51.2 (2) and 42.8 (2)°, respectively. In the crystal, two of the molecules are linked through N-HO hydrogen bonding to an adjoining molecule, forming dimers of the R₂²(10) type, while the third molecule forms such dimers with itself. C-HO interactions link the dimers.

Related literature

For graph-set description of hydrogen-bonding patterns, see: Bernstein et al. (1995). For related structures, see: Fun et al. (2011a,b, 2012a,b). For similar structures but with differing dichloro substitution, see: Butcher et al. (2013a,b). For a description of the Cambridge Structural Database, see: Allen (2002). For the biological activity of N-substituted 2-arylacetamides, see: Mijin & Marinkovic (2006); Mijin et al. (2008). For the coordination abilities of amides, see: Wu et al. (2008, 2010).

Experimental

Crystal data

C₁₉H₁₇Cl₂N₃O₂
M_r = 390.26
Monoclinic, P 2₁ /c
a = 17.2064 (8) Å
b = 20.7984 (9) Å
c = 15.6102 (7) Å
= 101.213 (4)°
V = 5479.7 (4) Å³
Z = 12
Mo K radiation
= 0.37 mm^-1
T = 123 K
0.51 × 0.34 × 0.10 mm

Data collection

Agilent Xcalibur (Ruby, Gemini) diffractometer
Absorption correction: analytical [CrysAlis PRO (Agilent, 2011) based on expressions derived by Clark & Reid (1995)] T_min = 0.743, T_max = 0.932
54403 measured reflections
27521 independent reflections
11938 reflections with I > 2(I)
R_int = 0.076

Refinement

R[F² > 2(F²)] = 0.119
wR(F²) = 0.345
S = 1.02
27521 reflections
709 parameters
H-atom parameters constrained
_max = 3.46 e Å^-3
_min = -0.84 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1A-H1AAO2Aⁱ	0.88	1.98	2.820 (3)	159
N1B-H1BAO2C	0.88	2.01	2.849 (3)	159
N1C-H1CAO2B	0.88	1.96	2.795 (3)	158
C11A-H11CO2Bⁱⁱ	0.98	2.39	3.344 (4)	163
C11C-H11HO2Aⁱⁱⁱ	0.98	2.45	3.377 (4)	158
C12C-H12GO2Aⁱⁱⁱ	0.98	2.44	3.186 (4)	133
C12C-H12HO1Bⁱⁱⁱ	0.98	2.51	3.178 (4)	125
C12A-H12AO2Bⁱⁱ	0.98	2.50	3.273 (4)	136
C11B-H11FO2C^iv	0.98	2.42	3.364 (4)	163
C12B-H12DO2C^iv	0.98	2.46	3.282 (4)	142
C17B-H17BCl1B^v	0.95	2.89	3.705 (4)	144
Symmetry codes: (i) -x+1, -y+1, -z+2; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (iv) -x+1, -y+1, -z+1; (v) x+1, y, z.

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG5286 ).

Acknowledgements

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.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Butcher, R. J., Mahan, A., Nayak, P. S., Narayana, B. & Yathirajan, H. S. (2013a). Acta Cryst. E69, o39.
Butcher, R. J., Mahan, A., Nayak, P. S., Narayana, B. & Yathirajan, H. S. (2013b). Acta Cryst. E69, o46-o47.
Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897.
Fun, H.-K., Quah, C. K., Narayana, B., Nayak, P. S. & Sarojini, B. K. (2011a). Acta Cryst. E67, o2926-o2927.
Fun, H.-K., Quah, C. K., Narayana, B., Nayak, P. S. & Sarojini, B. K. (2011b). Acta Cryst. E67, o2941-o2942.
Fun, H.-K., Quah, C. K., Nayak, P. S., Narayana, B. & Sarojini, B. K. (2012a). Acta Cryst. E68, o2677.
Fun, H.-K., Shahani, T., Nayak, P. S., Narayana, B. & Sarojini, B. K. (2012b). Acta Cryst. E68, o519.
Mijin, D. & Marinkovic, A. (2006). Synth. Commun. 36, 193-198.
Mijin, D. Z., Prascevic, M. & Petrovic, S. D. (2008). J. Serb. Chem. Soc. 73, 945-950.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Wu, W.-N., Cheng, F.-X., Yan, L. & Tang, N. (2008). J. Coord. Chem. 61, 2207-2215.
Wu, W.-N., Wang, Y., Zhang, A.-Y., Zhao, R.-Q. & Wang, Q.-F. (2010). Acta Cryst. E66, m288.

organic compounds