(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

organic compounds

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ISSN: 2056-9890

Volume 66| Part 10| October 2010| Pages o2594-o2595

doi:10.1107/S1600536810035646

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(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

(Received 16 July 2010; accepted 5 September 2010; online 18 September 2010)

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—H⋯Cl interactions. These dimers are further linked through a C—H⋯O hydrogen bond, forming a C(8) chain extending along the a axis. C—H⋯π 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
α = 90.533 (7)°
β = 116.924 (4)°
γ = 93.427 (6)°
V = 801.38 (9) Å³
Z = 2
Mo Kα radiation
μ = 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 > 2σ(I)
R_int = 0.018

Refinement

R[F² > 2σ(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
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C31–C36 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯Cl2ⁱ	0.93	2.93	3.6447 (16)	134
C14—H14⋯O1ⁱⁱ	0.93	2.49	3.407 (2)	167
C36—H36⋯Cl1ⁱⁱⁱ	0.93	2.90	3.6334 (16)	137
C17—H17⋯Cg1^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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810035646/fb2206sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810035646/fb2206Isup2.hkl

checkCIF report

Comment top

Pyrazole and its derivatives have been successfully tested for their fungicidal (Chen & Li, 1998), antihistaminic (Mishra et al., 1998), anti-inflammatory (Smith et al., 2001), antiarrhythmic and sedative (Bruno et al., 1990), hypoglycemic (Cottineau et al., 2002), antiviral (Baraldi et al., 1998) activities. Pyrazole derivates possess antimicrobial (Velaparthi et al.,2008), anticancer (Magedov et al., 2007) and anti-inflammatory (Rovnyak et al., 1982) properties. They can also be used as biodegradable agrochemicals (Wamhoff et al., 1993) as well as pesticides (Londershausen, 1996). Wide variety of biological effects of these molecules provoked interest for their crystal structure study and accordingly we have synthesized the title compound by multi-component reaction which conforms to principles of green chemistry. The crystal structure of the title compound is reported here.

The title molecule is shown in Fig. 1. The pyrazole ring is planar with the r.m.s. deviation equal to 0.002 Å. The sum of the bond angles at N1 of the pyrazole ring (359.7 (1)°) is in accordance with the sp² hybridization of this atom (Beddoes et al., 1986). The C—N bond lengths in the pyrazole ring are 1.370 (2) [C5-N1] and 1.327 (2)Å [C3-N2] long. These distances are shorter than the pertinent single bond length (1.443 Å), however, they are longer than the double bond length (1.269 Å) (Jin et al., 2004). The values of these distances in the title structure indicate electron delocalization.

The two chlorophenyl rings are twisted out from the plane of the pyrazole ring with respective angles of 5.3 (1)° (C31//C36 ring) and 65.34 (4)° (C12//C17 ring). The propenal group assumes the extended conformation which is evidenced by the torsion angles of 173.3 (1)° [N1-C11-C1A-C2A] and 157.0 (2)° [C5-N1-C11-C1A]. The crystal structure is stabilized by intermolecular C—H···Cl, C—H···O and C—H···π-electron ring interactions (Tab. 1). The packing diagram of the title compound is shown in Fig. 2.

Each of two centrosymmetric R²₂(24) dimers (Etter et al., 1990) are formed around the crystallographic inversion centres through a pair of the respective C—H···Cl interactions (Figs. 3 and 4 referring to C13—H13···Cl2 and C36—H36···Cl1, respectively; Tab. 1). Though the latter H···Cl distances are somewhat longer by about 0.5Å than the accepted values for the C-H···Cl hydrogen bonding (Desiraju & Steiner, 1999) these dimers are an important motif in the present structure and therefore they are reported here.

These dimers are linked through a C—H···O bond making a chain C(8) motif (Etter et al., 1990) that extends along the a axis of the unit cell (Fig. 5). Further, one of these primary ring R²₂(24) motifs and the chain C(8) motif are combined to form a secondary ring R⁴₄(32) motif (Fig. 6). Also, the C—H···π-electron ring interactions are observed in the structure. The crystallographic inversions link the latter motifs into pairs, forming another ring motif.

Related literature top

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 top

To a mixture of 1-(4-chlorophenyl)-1-ethanone N-[(E)-1-(4-chlorophenyl)ethylidene]hydrazone (0.003 mole) and 3 ml of dimethyl formamide kept in ice bath at 0°C, phosphorous oxycholride (0.024 mole) was added dropwise in 5 to 10 minutes. The reaction mixture was then irradiated under microwaves for 30 sec using a Biotage Microwave Synthesizer (frequency 2.45 GHz corresponding to the wavelength equal to 12.24 cm). The process of the reaction was monitored by thin layer chromatography using petroleum ether and ethyl acetate (4:1 v/v) as an eluent. The R_f value of the product was 0.62. After completion of the reaction, the reaction mixture was poured into crushed ice and extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate. The title compound was separated by column chromatography: carrier: silica gel (60-120 mesh), eluent: petroleum ether and ethyl acetate mixture (98:2 v/v). The compound was crystallized from dichloromethane. Colourless crystals of a prismatic habitus with the average size of 0.5 × 0.5 × 0.2 cm were grown within a week.

Computing details top

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

Figures top

	Fig. 1. The title molecule with the atom numbering scheme. The displacement ellipsoids are shown at the 50% probability level.
	Fig. 2. Packing diagram of the title structure viewed down the a axis. (Cl is shown in green, N in blue, O in red, C in black and H as a circle.)
	Fig. 3. Ring R²₂(24) motif involving the C13—H13···Cl2 interactions. These interactions are drawn as dashed lines. (Cl is shown in green, N in blue, O in red, C in black and H in violet.)
	Fig. 4. Ring R²₂(24) motif involving the C36—H36···Cl1 interactions. These interactions are drawn as dashed lines. (Cl is shown in green, N in blue, O in red, C in black and H in violet.)
	Fig. 5. Chain C(8) motif involving the C14—H14···O1 hydrogen bond. The hydrogen bonds are drawn as dashed lines. (Cl is shown in green, N in blue, O in red, C in black and H in violet.)
	Fig. 6. Secondary ring R⁴₄(32) motif formed by a combination of the ring R²₂(24) and the chain C(8) motifs. The C—H···O bonds and C—H···Cl interactions are drawn as dashed lines. (Cl is shown in green, N in blue, O in red, C in black and H in violet.)

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

Crystal data top

C₁₈H₁₂Cl₂N₂O	Z = 2
M_r = 343.20	F(000) = 352
Triclinic, P1	D_x = 1.422 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.4321 (6) Å	Cell parameters from 4879 reflections
b = 9.6081 (5) Å	θ = 2.4–24.7°
c = 9.9439 (7) Å	µ = 0.41 mm⁻¹
α = 90.533 (7)°	T = 293 K
β = 116.924 (4)°	Block, colourless
γ = 93.427 (6)°	0.16 × 0.14 × 0.12 mm
V = 801.38 (9) Å³

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3464 independent reflections
Radiation source: fine-focus sealed tube	2982 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.018
ω scans	θ_max = 27.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −12→11
T_min = 0.884, T_max = 0.993	k = −12→12
8950 measured reflections	l = −12→12

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.040	Hydrogen site location: difference Fourier map
wR(F²) = 0.116	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.064P)² + 0.1138P] where P = (F_o² + 2F_c²)/3
3464 reflections	(Δ/σ)_max < 0.001
211 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₁₈H₁₂Cl₂N₂O	γ = 93.427 (6)°
M_r = 343.20	V = 801.38 (9) Å³
Triclinic, P1	Z = 2
a = 9.4321 (6) Å	Mo Kα radiation
b = 9.6081 (5) Å	µ = 0.41 mm⁻¹
c = 9.9439 (7) Å	T = 293 K
α = 90.533 (7)°	0.16 × 0.14 × 0.12 mm
β = 116.924 (4)°

Data collection top

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

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.116	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.20 e Å⁻³
3464 reflections	Δρ_min = −0.24 e Å⁻³
211 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
N1	0.32051 (15)	0.14597 (14)	0.94391 (16)	0.0637 (3)
N2	0.33330 (15)	0.11932 (14)	0.81571 (16)	0.0645 (3)
C3	0.23105 (17)	0.01018 (15)	0.74769 (19)	0.0609 (4)
C4	0.1527 (2)	−0.03430 (17)	0.8341 (2)	0.0703 (4)
H4	0.0765	−0.1085	0.8109	0.084*
C5	0.2117 (2)	0.05315 (17)	0.9566 (2)	0.0704 (4)
H5	0.1838	0.0510	1.0351	0.084*
C11	0.42212 (17)	0.24992 (16)	1.05026 (18)	0.0616 (4)
C12	0.36968 (16)	0.29488 (15)	1.16169 (18)	0.0588 (3)
C13	0.21605 (17)	0.33822 (17)	1.1154 (2)	0.0656 (4)
H13	0.1469	0.3408	1.0129	0.079*
C14	0.16603 (17)	0.37703 (17)	1.2194 (2)	0.0674 (4)
H14	0.0635	0.4053	1.1877	0.081*
C15	0.26958 (18)	0.37363 (15)	1.3718 (2)	0.0617 (4)
C16	0.42360 (18)	0.33354 (15)	1.42098 (19)	0.0625 (4)
H16	0.4931	0.3333	1.5235	0.075*
C17	0.47177 (16)	0.29416 (15)	1.31565 (18)	0.0604 (4)
H17	0.5746	0.2665	1.3479	0.072*
C31	0.21217 (16)	−0.04755 (15)	0.60370 (19)	0.0596 (4)
C32	0.2953 (2)	0.01493 (17)	0.5314 (2)	0.0679 (4)
H32	0.3586	0.0971	0.5730	0.082*
C33	0.28550 (19)	−0.04239 (17)	0.4007 (2)	0.0695 (4)
H33	0.3421	0.0002	0.3544	0.083*
C34	0.19066 (18)	−0.16420 (17)	0.33797 (18)	0.0637 (4)
C35	0.10245 (17)	−0.22597 (17)	0.4035 (2)	0.0670 (4)
H35	0.0357	−0.3059	0.3590	0.080*
C36	0.11458 (17)	−0.16782 (16)	0.5355 (2)	0.0651 (4)
H36	0.0561	−0.2099	0.5803	0.078*
C1A	0.55695 (18)	0.29870 (18)	1.0452 (2)	0.0694 (4)
H1A	0.5853	0.2553	0.9778	0.083*
C2A	0.65832 (19)	0.4138 (2)	1.1383 (2)	0.0739 (4)
O1	0.78899 (15)	0.44765 (18)	1.14726 (18)	0.0993 (5)
Cl1	0.20652 (6)	0.41935 (5)	1.50378 (6)	0.08373 (18)
Cl2	0.18660 (6)	−0.24132 (5)	0.17751 (5)	0.08459 (18)
H2A	0.612 (3)	0.475 (2)	1.198 (3)	0.102*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0550 (7)	0.0618 (7)	0.0774 (8)	0.0047 (6)	0.0326 (6)	0.0104 (6)
N2	0.0554 (7)	0.0635 (7)	0.0762 (8)	0.0042 (6)	0.0312 (6)	0.0107 (6)
C3	0.0500 (7)	0.0530 (7)	0.0810 (10)	0.0102 (6)	0.0297 (7)	0.0162 (7)
C4	0.0665 (9)	0.0589 (8)	0.0926 (12)	0.0006 (7)	0.0427 (9)	0.0115 (8)
C5	0.0654 (9)	0.0641 (9)	0.0900 (11)	0.0033 (7)	0.0426 (9)	0.0148 (8)
C11	0.0475 (7)	0.0620 (8)	0.0726 (9)	0.0099 (6)	0.0240 (7)	0.0146 (7)
C12	0.0444 (7)	0.0553 (7)	0.0743 (9)	0.0047 (6)	0.0247 (6)	0.0127 (7)
C13	0.0443 (7)	0.0698 (9)	0.0745 (9)	0.0073 (6)	0.0194 (7)	0.0093 (7)
C14	0.0446 (7)	0.0643 (9)	0.0910 (11)	0.0056 (6)	0.0285 (8)	0.0058 (8)
C15	0.0550 (8)	0.0488 (7)	0.0830 (10)	−0.0070 (6)	0.0341 (7)	0.0005 (7)
C16	0.0532 (8)	0.0544 (7)	0.0722 (9)	−0.0030 (6)	0.0225 (7)	0.0081 (7)
C17	0.0432 (7)	0.0573 (8)	0.0747 (9)	0.0061 (6)	0.0211 (6)	0.0139 (7)
C31	0.0450 (7)	0.0536 (7)	0.0775 (9)	0.0098 (6)	0.0246 (7)	0.0167 (7)
C32	0.0617 (9)	0.0571 (8)	0.0812 (10)	−0.0050 (7)	0.0300 (8)	0.0110 (7)
C33	0.0612 (9)	0.0686 (9)	0.0755 (10)	−0.0059 (7)	0.0293 (8)	0.0144 (8)
C34	0.0489 (7)	0.0652 (8)	0.0669 (9)	0.0057 (6)	0.0171 (6)	0.0132 (7)
C35	0.0483 (7)	0.0608 (8)	0.0811 (10)	−0.0025 (6)	0.0205 (7)	0.0100 (7)
C36	0.0477 (7)	0.0605 (8)	0.0856 (11)	0.0009 (6)	0.0290 (7)	0.0138 (8)
C1A	0.0498 (8)	0.0802 (10)	0.0790 (10)	0.0084 (7)	0.0292 (7)	0.0104 (8)
C2A	0.0507 (8)	0.0877 (11)	0.0792 (11)	0.0029 (8)	0.0260 (8)	0.0168 (9)
O1	0.0524 (7)	0.1234 (12)	0.1192 (12)	−0.0071 (7)	0.0379 (7)	0.0170 (9)
Cl1	0.0797 (3)	0.0800 (3)	0.1033 (4)	−0.0142 (2)	0.0546 (3)	−0.0152 (2)
Cl2	0.0784 (3)	0.0921 (3)	0.0749 (3)	−0.0089 (2)	0.0293 (2)	−0.0005 (2)

Geometric parameters (Å, º) top

N1—N2	1.357 (2)	C16—C17	1.375 (2)
N1—C5	1.370 (2)	C16—H16	0.9300
N1—C11	1.408 (2)	C17—H17	0.9300
N2—C3	1.327 (2)	C31—C36	1.391 (2)
C3—C4	1.418 (2)	C31—C32	1.398 (2)
C3—C31	1.460 (2)	C32—C33	1.369 (2)
C4—C5	1.346 (3)	C32—H32	0.9300
C4—H4	0.9300	C33—C34	1.384 (2)
C5—H5	0.9300	C33—H33	0.9300
C11—C1A	1.351 (2)	C34—C35	1.382 (2)
C11—C12	1.474 (2)	C34—Cl2	1.7366 (18)
C12—C17	1.392 (2)	C35—C36	1.375 (2)
C12—C13	1.399 (2)	C35—H35	0.9300
C13—C14	1.374 (2)	C36—H36	0.9300
C13—H13	0.9300	C1A—C2A	1.431 (3)
C14—C15	1.384 (2)	C1A—H1A	0.9300
C14—H14	0.9300	C2A—O1	1.219 (2)
C15—C16	1.387 (2)	C2A—H2A	1.07 (2)
C15—Cl1	1.7313 (17)

N2—N1—C5	111.32 (14)	C17—C16—H16	120.5
N2—N1—C11	120.54 (13)	C15—C16—H16	120.5
C5—N1—C11	127.88 (15)	C16—C17—C12	121.30 (13)
C3—N2—N1	105.24 (13)	C16—C17—H17	119.3
N2—C3—C4	110.62 (16)	C12—C17—H17	119.3
N2—C3—C31	120.42 (14)	C36—C31—C32	117.70 (16)
C4—C3—C31	128.96 (15)	C36—C31—C3	121.53 (14)
C5—C4—C3	105.75 (15)	C32—C31—C3	120.75 (14)
C5—C4—H4	127.1	C33—C32—C31	121.34 (15)
C3—C4—H4	127.1	C33—C32—H32	119.3
C4—C5—N1	107.06 (16)	C31—C32—H32	119.3
C4—C5—H5	126.5	C32—C33—C34	119.49 (15)
N1—C5—H5	126.5	C32—C33—H33	120.3
C1A—C11—N1	119.59 (16)	C34—C33—H33	120.3
C1A—C11—C12	125.45 (15)	C35—C34—C33	120.66 (16)
N1—C11—C12	114.95 (13)	C35—C34—Cl2	120.04 (13)
C17—C12—C13	118.47 (15)	C33—C34—Cl2	119.29 (13)
C17—C12—C11	120.65 (13)	C36—C35—C34	119.15 (15)
C13—C12—C11	120.88 (14)	C36—C35—H35	120.4
C14—C13—C12	120.84 (15)	C34—C35—H35	120.4
C14—C13—H13	119.6	C35—C36—C31	121.60 (15)
C12—C13—H13	119.6	C35—C36—H36	119.2
C13—C14—C15	119.37 (14)	C31—C36—H36	119.2
C13—C14—H14	120.3	C11—C1A—C2A	123.32 (17)
C15—C14—H14	120.3	C11—C1A—H1A	118.3
C14—C15—C16	121.07 (15)	C2A—C1A—H1A	118.3
C14—C15—Cl1	119.74 (12)	O1—C2A—C1A	123.47 (19)
C16—C15—Cl1	119.20 (13)	O1—C2A—H2A	119.7 (13)
C17—C16—C15	118.93 (15)	C1A—C2A—H2A	116.7 (13)

C5—N1—N2—C3	0.51 (16)	C14—C15—C16—C17	−1.3 (2)
C11—N1—N2—C3	175.14 (12)	Cl1—C15—C16—C17	178.47 (11)
N1—N2—C3—C4	−0.49 (16)	C15—C16—C17—C12	0.5 (2)
N1—N2—C3—C31	179.66 (12)	C13—C12—C17—C16	0.7 (2)
N2—C3—C4—C5	0.30 (18)	C11—C12—C17—C16	−178.87 (13)
C31—C3—C4—C5	−179.86 (14)	N2—C3—C31—C36	175.27 (13)
C3—C4—C5—N1	0.03 (18)	C4—C3—C31—C36	−4.6 (2)
N2—N1—C5—C4	−0.34 (18)	N2—C3—C31—C32	−3.1 (2)
C11—N1—C5—C4	−174.48 (14)	C4—C3—C31—C32	177.04 (15)
N2—N1—C11—C1A	−16.7 (2)	C36—C31—C32—C33	−2.1 (2)
C5—N1—C11—C1A	156.99 (16)	C3—C31—C32—C33	176.38 (14)
N2—N1—C11—C12	164.21 (12)	C31—C32—C33—C34	0.4 (2)
C5—N1—C11—C12	−22.1 (2)	C32—C33—C34—C35	1.9 (2)
C1A—C11—C12—C17	−52.2 (2)	C32—C33—C34—Cl2	−176.72 (12)
N1—C11—C12—C17	126.86 (15)	C33—C34—C35—C36	−2.4 (2)
C1A—C11—C12—C13	128.27 (18)	Cl2—C34—C35—C36	176.17 (11)
N1—C11—C12—C13	−52.66 (19)	C34—C35—C36—C31	0.7 (2)
C17—C12—C13—C14	−1.0 (2)	C32—C31—C36—C35	1.5 (2)
C11—C12—C13—C14	178.48 (14)	C3—C31—C36—C35	−176.91 (13)
C12—C13—C14—C15	0.3 (2)	N1—C11—C1A—C2A	173.32 (15)
C13—C14—C15—C16	0.9 (2)	C12—C11—C1A—C2A	−7.7 (3)
C13—C14—C15—Cl1	−178.85 (12)	C11—C1A—C2A—O1	170.98 (18)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C31–C36 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···Cl2ⁱ	0.93	2.93	3.6447 (16)	134
C14—H14···O1ⁱⁱ	0.93	2.49	3.407 (2)	167
C36—H36···Cl1ⁱⁱⁱ	0.93	2.90	3.6334 (16)	137
C17—H17···Cg1^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.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₂Cl₂N₂O
M_r	343.20
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	9.4321 (6), 9.6081 (5), 9.9439 (7)
α, β, γ (°)	90.533 (7), 116.924 (4), 93.427 (6)
V (Å³)	801.38 (9)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.41
Crystal size (mm)	0.16 × 0.14 × 0.12

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2001)
T_min, T_max	0.884, 0.993
No. of measured, independent and observed [I > 2σ(I)] reflections	8950, 3464, 2982
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.116, 1.04
No. of reflections	3464
No. of parameters	211
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.24

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXTL/PC (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C31–C36 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···Cl2ⁱ	0.93	2.93	3.6447 (16)	134.3
C14—H14···O1ⁱⁱ	0.93	2.49	3.407 (2)	167.4
C36—H36···Cl1ⁱⁱⁱ	0.93	2.90	3.6334 (16)	137.2
C17—H17···Cg1^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.

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.

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Volume 66| Part 10| October 2010| Pages o2594-o2595

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