(E)-3-(4-Chloro­phen­yl)-3-[3-(4-chloro­phen­yl)-1H-pyrazol-1-yl]prop-2-enal

Susindran, V.; Athimoolam, S.; Bahadur, S.A.; Manikannan, R.; Muthusubramanian, S.

doi:10.1107/S1600536810035646

Volume 66
Part 10
Pages o2594-o2595
October 2010

Received 16 July 2010
Accepted 5 September 2010
Online 18 September 2010

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
R = 0.040
wR = 0.116
Data-to-parameter ratio = 16.4
Details

(E)-3-(4-Chlorophenyl)-3-[3-(4-chlorophenyl)-1H-pyrazol-1-yl]prop-2-enal

V. Susindran,^a S. Athimoolam,^b S. Asath Bahadur,^c ^* R. Manikannan ^d and S. Muthusubramanian ^d

^aDepartment of Lighthouses & Lightships, Ministry of Shipping, Nagapattinam Lighthouse & DGPS station, Nagapattinam 611 001, India,^bDepartment of Physics, University College of Engineering Nagercoil, Anna University Tirunelveli, Nagercoil 629 004, India,^cDepartment of Physics, Kalasalingam University, Anand Nagar, Krishnan Koil 626 190, India, and ^dDepartment of Organic Chemistry, Madurai Kamaraj University, Madurai 625 021, India
Correspondence e-mail: s_a_bahadur@yahoo.co.in

In the title compound, C₁₈H₁₂Cl₂N₂O, the pyrazole ring is almost planar [r.m.s. deviation = 0.002 Å] while the two chlorophenyl rings are twisted out from the plane of the pyrazole ring, making dihedral angles of 5.3 (1) and 65.34 (4)°. In the crystal, centrosymmetric R₂²(24) dimers are formed about crystallographic inversion centres through a pair of C-HCl interactions. These dimers are further linked through a C-HO hydrogen bond, forming a C(8) chain extending along the a axis. C-H [pi] interactions are also observed.

Related literature

For the pharmacological properties of pyrazoles and their derivatives, see: Baraldi et al. (1998); Bruno et al. (1990); Chen & Li (1998); Cottineau et al. (2002); Londershausen (1996); Mishra et al. (1998); Magedov et al. (2007); Rovnyak et al. (1982); Smith et al. (2001); Velaparthi et al. (2008); Wamhoff et al. (1993). For hybridization and electron delocalization around N atoms, see: Beddoes et al. (1986); Jin et al. (2004). For hydrogen bonding, see: Desiraju & Steiner (1999) and for hydrogen-bond motifs, see: Etter et al. (1990).

Experimental

Crystal data

C₁₈H₁₂Cl₂N₂O
M_r = 343.20
Triclinic, $[P \overline 1]$
a = 9.4321 (6) Å
b = 9.6081 (5) Å
c = 9.9439 (7) Å
= 90.533 (7)°
= 116.924 (4)°
= 93.427 (6)°
V = 801.38 (9) Å³
Z = 2
Mo K radiation
= 0.41 mm^-1
T = 293 K
0.16 × 0.14 × 0.12 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2001) T_min = 0.884, T_max = 0.993
8950 measured reflections
3464 independent reflections
2982 reflections with I > 2(I)
R_int = 0.018

Refinement

R[F² > 2(F²)] = 0.040
wR(F²) = 0.116
S = 1.04
3464 reflections
211 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.20 e Å^-3
_min = -0.24 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C31-C36 ring.

D-HA	D-H	HA	DA	D-HA
C13-H13Cl2ⁱ	0.93	2.93	3.6447 (16)	134
C14-H14O1ⁱⁱ	0.93	2.49	3.407 (2)	167
C36-H36Cl1ⁱⁱⁱ	0.93	2.90	3.6334 (16)	137
C17-H17Cg1^iv	0.93	2.68	3.4919 (18)	147
Symmetry codes: (i) -x, -y, -z+1; (ii) x-1, y, z; (iii) -x, -y, -z+2; (iv) -x+1, -y, -z+2.

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXTL/PC (Sheldrick, 2008); program(s) used to refine structure: SHELXTL/PC; molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL/PC.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FB2206 ).

Acknowledgements

VS and SAB sincerely thank the Vice Chancellor and Management of Kalasalingam University, Anand Nagar, Krishnan Koil, for their support and encouragement. SA thanks the Vice-Chancellor of Anna University, Tirunelveli, for his support and encouragement.

References

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organic compounds