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

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

doi:10.1107/S1600536812049628

Volume 69
Part 1
Page o39
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 (C-C) = 0.002 Å
R = 0.035
wR = 0.095
Data-to-parameter ratio = 16.2
Details

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

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

^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 crystal structure of the title compound, C₁₉H₁₇Cl₂N₃O₂, the molecules form dimers of the R₂²(10) type through N-HO hydrogen bonding. 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 80.70 (13) and 64.82 (12)°, respectively. The dihedral angle between the dichlorophenyl and 2,3-dihydro-1H-pyrazol-4-yl rings is 48.45 (5)° while that between the 2,3-dihydro-1H-pyrazol-4-yl and phenyl rings is 56.33 (6)°.

Related literature

For a description of the Cambridge Structural Database, see: Allen (2002). For hydrogen-bond motifs, see: Bernstein et al. (1995). For N-substituted 2-arylacetamides and amides, see: Mijin & Marinkovic (2006); Mijin et al. (2008); Fun et al. (2011a,b); Fun, Shahani et al. (2012); Fun, Quah et al. (2012); Wu et al. (2008, 2010).

Experimental

Crystal data

C₁₉H₁₇Cl₂N₃O₂
M_r = 390.26
Monoclinic, C 2/c
a = 25.1853 (5) Å
b = 8.18108 (9) Å
c = 21.0978 (4) Å
= 119.772 (3)°
V = 3773.26 (16) Å³
Z = 8
Cu K radiation
= 3.25 mm^-1
T = 123 K
0.59 × 0.22 × 0.08 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 = 0.429, T_max = 0.804
12628 measured reflections
3849 independent reflections
3663 reflections with I > 2(I)
R_int = 0.027

Refinement

R[F² > 2(F²)] = 0.035
wR(F²) = 0.095
S = 1.05
3849 reflections
237 parameters
H-atom parameters constrained
_max = 0.57 e Å^-3
_min = -0.30 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1AO2ⁱ	0.88	1.92	2.7938 (15)	171
Symmetry code: (i) $[-x+1, y, -z+{\script{3\over 2}}]$ .

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: BT6879 ).

Acknowledgements

RJB acknowledges the NSF-MRI program (grant No. CHE-0619278) for funds to purchase the diffractometer.

References

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organic compounds