organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
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ISSN: 2056-9890
Volume 66| Part 10| October 2010| Pages o2594-o2595

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

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[Baraldi, P. G., Manfredini, S., Romagnoli, R., Stevanato, L., Zaid, A. N. & Manservigi, R. (1998). Nucleosides Nucleotides, 17, 2165-2171.]); Bruno et al. (1990[Bruno, O., Bondavalli, F., Ranise, A., Schenone, P., Losasso, C., Cilenti, L., Matera, C. & Marmo, E. (1990). Farmaco, 45, 147-166.]); Chen & Li (1998[Chen, H. S. & Li, Z. M. (1998). Chem. J. Chin. Univ. 19, 572-576.]); Cottineau et al. (2002[Cottineau, B., Toto, P., Marot, C., Pipaud, A. & Chenault, J. (2002). Bioorg. Med. Chem. 12, 2105-2108.]); Londershausen (1996[Londershausen, M. (1996). Pestic. Sci. 48, 269-274.]); Mishra et al. (1998[Mishra, P. D., Wahidullah, S. & Kamat, S. Y. (1998). Indian J. Chem. Sect. B, 37, 199-200.]); Magedov et al. (2007[Magedov, I. V., Manpadi, M., Vanslambrouck, S., Steelant, W. F. A., Rozhkova, E., Przhevalskii, N. M., Rogelj, S. & Kornienko, A. (2007). J. Med. Chem. 50, 5183-5192.]); Rovnyak et al. (1982[Rovnyak, G. C., Millonig, R. C., Schwartz, J. & Shu, V. (1982). J. Med. Chem. 25, 1482-1488.]); Smith et al. (2001[Smith, S. R., Denhardt, G. & Terminelli, C. (2001). Eur. J. Pharmacol. 432, 107-119.]); Velaparthi et al. (2008[Velaparthi, S., Brunsteiner, M., Uddin, R., Wan, B., Franzblau, S. G. & Petukhov, P. A. (2008). J. Med. Chem. 51, 1999-2002.]); Wamhoff et al. (1993[Wamhoff, H., Kroth, E. & Strauch, K. (1993). Synthesis, 11, 1129-1132.]). For hybridization and electron delocalization around N atoms, see: Beddoes et al. (1986[Beddoes, R. L., Dalton, L., Joule, T. A., Mills, O. S., Street, J. D. & Watt, C. I. F. (1986). J. Chem. Soc. Perkin Trans. 2, pp. 787-797.]); Jin et al. (2004[Jin, Z.-M., Li, L., Li, M.-C., Hu, M.-L. & Shen, L. (2004). Acta Cryst. C60, o642-o643.]). For hydrogen bonding, see: Desiraju & Steiner (1999[Desiraju, G. R. & Steiner, T. (1999). The Weak Hydrogen Bond in Structural Chemistry and Biology, pp. 246-253. IUCr Monographs on Crystallography. Oxford University Press.]) and for hydrogen-bond motifs, see: Etter et al. (1990[Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.]).

[Scheme 1]

Experimental

Crystal data
  • C18H12Cl2N2O

  • Mr = 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[Sheldrick, G. M. (2001). SADABS. University of Göttingen, Germany.]) Tmin = 0.884, Tmax = 0.993

  • 8950 measured reflections

  • 3464 independent reflections

  • 2982 reflections with I > 2σ(I)

  • Rint = 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

  • Δρmax = 0.20 e Å−3

  • Δρmin = −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 DA 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⋯Cg1iv 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[Bruker (2001). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL/PC (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL/PC; molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXTL/PC.

Supporting information


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 Rf 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.

Refinement top

All the H atoms were observable in the difference electron density map. All the hydrogens except the one from the aldehyde group were situated into the idealized positions and refined by the riding model approximation. The used values for the constraints: d(C—H) = 0.93 Å. Uiso(H)= 1.2Ueq(C). The positional parameters of the aldehyde hydrogen were refined freely while Uiso(H)= 1.2Ueq(C).

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
[Figure 1] Fig. 1. The title molecule with the atom numbering scheme. The displacement ellipsoids are shown at the 50% probability level.
[Figure 2] 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.)
[Figure 3] 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.)
[Figure 4] 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.)
[Figure 5] 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.)
[Figure 6] 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
C18H12Cl2N2OZ = 2
Mr = 343.20F(000) = 352
Triclinic, P1Dx = 1.422 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.4321 (6) ÅCell parameters from 4879 reflections
b = 9.6081 (5) Åθ = 2.4–24.7°
c = 9.9439 (7) ŵ = 0.41 mm1
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 tube2982 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.018
ω scansθmax = 27.0°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2001)
h = 1211
Tmin = 0.884, Tmax = 0.993k = 1212
8950 measured reflectionsl = 1212
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040Hydrogen site location: difference Fourier map
wR(F2) = 0.116H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.064P)2 + 0.1138P]
where P = (Fo2 + 2Fc2)/3
3464 reflections(Δ/σ)max < 0.001
211 parametersΔρmax = 0.20 e Å3
0 restraintsΔρmin = 0.24 e Å3
Crystal data top
C18H12Cl2N2Oγ = 93.427 (6)°
Mr = 343.20V = 801.38 (9) Å3
Triclinic, P1Z = 2
a = 9.4321 (6) ÅMo Kα radiation
b = 9.6081 (5) ŵ = 0.41 mm1
c = 9.9439 (7) ÅT = 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)
Tmin = 0.884, Tmax = 0.993Rint = 0.018
8950 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0400 restraints
wR(F2) = 0.116H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.20 e Å3
3464 reflectionsΔρmin = 0.24 e Å3
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
xyzUiso*/Ueq
N10.32051 (15)0.14597 (14)0.94391 (16)0.0637 (3)
N20.33330 (15)0.11932 (14)0.81571 (16)0.0645 (3)
C30.23105 (17)0.01018 (15)0.74769 (19)0.0609 (4)
C40.1527 (2)0.03430 (17)0.8341 (2)0.0703 (4)
H40.07650.10850.81090.084*
C50.2117 (2)0.05315 (17)0.9566 (2)0.0704 (4)
H50.18380.05101.03510.084*
C110.42212 (17)0.24992 (16)1.05026 (18)0.0616 (4)
C120.36968 (16)0.29488 (15)1.16169 (18)0.0588 (3)
C130.21605 (17)0.33822 (17)1.1154 (2)0.0656 (4)
H130.14690.34081.01290.079*
C140.16603 (17)0.37703 (17)1.2194 (2)0.0674 (4)
H140.06350.40531.18770.081*
C150.26958 (18)0.37363 (15)1.3718 (2)0.0617 (4)
C160.42360 (18)0.33354 (15)1.42098 (19)0.0625 (4)
H160.49310.33331.52350.075*
C170.47177 (16)0.29416 (15)1.31565 (18)0.0604 (4)
H170.57460.26651.34790.072*
C310.21217 (16)0.04755 (15)0.60370 (19)0.0596 (4)
C320.2953 (2)0.01493 (17)0.5314 (2)0.0679 (4)
H320.35860.09710.57300.082*
C330.28550 (19)0.04239 (17)0.4007 (2)0.0695 (4)
H330.34210.00020.35440.083*
C340.19066 (18)0.16420 (17)0.33797 (18)0.0637 (4)
C350.10245 (17)0.22597 (17)0.4035 (2)0.0670 (4)
H350.03570.30590.35900.080*
C360.11458 (17)0.16782 (16)0.5355 (2)0.0651 (4)
H360.05610.20990.58030.078*
C1A0.55695 (18)0.29870 (18)1.0452 (2)0.0694 (4)
H1A0.58530.25530.97780.083*
C2A0.65832 (19)0.4138 (2)1.1383 (2)0.0739 (4)
O10.78899 (15)0.44765 (18)1.14726 (18)0.0993 (5)
Cl10.20652 (6)0.41935 (5)1.50378 (6)0.08373 (18)
Cl20.18660 (6)0.24132 (5)0.17751 (5)0.08459 (18)
H2A0.612 (3)0.475 (2)1.198 (3)0.102*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0550 (7)0.0618 (7)0.0774 (8)0.0047 (6)0.0326 (6)0.0104 (6)
N20.0554 (7)0.0635 (7)0.0762 (8)0.0042 (6)0.0312 (6)0.0107 (6)
C30.0500 (7)0.0530 (7)0.0810 (10)0.0102 (6)0.0297 (7)0.0162 (7)
C40.0665 (9)0.0589 (8)0.0926 (12)0.0006 (7)0.0427 (9)0.0115 (8)
C50.0654 (9)0.0641 (9)0.0900 (11)0.0033 (7)0.0426 (9)0.0148 (8)
C110.0475 (7)0.0620 (8)0.0726 (9)0.0099 (6)0.0240 (7)0.0146 (7)
C120.0444 (7)0.0553 (7)0.0743 (9)0.0047 (6)0.0247 (6)0.0127 (7)
C130.0443 (7)0.0698 (9)0.0745 (9)0.0073 (6)0.0194 (7)0.0093 (7)
C140.0446 (7)0.0643 (9)0.0910 (11)0.0056 (6)0.0285 (8)0.0058 (8)
C150.0550 (8)0.0488 (7)0.0830 (10)0.0070 (6)0.0341 (7)0.0005 (7)
C160.0532 (8)0.0544 (7)0.0722 (9)0.0030 (6)0.0225 (7)0.0081 (7)
C170.0432 (7)0.0573 (8)0.0747 (9)0.0061 (6)0.0211 (6)0.0139 (7)
C310.0450 (7)0.0536 (7)0.0775 (9)0.0098 (6)0.0246 (7)0.0167 (7)
C320.0617 (9)0.0571 (8)0.0812 (10)0.0050 (7)0.0300 (8)0.0110 (7)
C330.0612 (9)0.0686 (9)0.0755 (10)0.0059 (7)0.0293 (8)0.0144 (8)
C340.0489 (7)0.0652 (8)0.0669 (9)0.0057 (6)0.0171 (6)0.0132 (7)
C350.0483 (7)0.0608 (8)0.0811 (10)0.0025 (6)0.0205 (7)0.0100 (7)
C360.0477 (7)0.0605 (8)0.0856 (11)0.0009 (6)0.0290 (7)0.0138 (8)
C1A0.0498 (8)0.0802 (10)0.0790 (10)0.0084 (7)0.0292 (7)0.0104 (8)
C2A0.0507 (8)0.0877 (11)0.0792 (11)0.0029 (8)0.0260 (8)0.0168 (9)
O10.0524 (7)0.1234 (12)0.1192 (12)0.0071 (7)0.0379 (7)0.0170 (9)
Cl10.0797 (3)0.0800 (3)0.1033 (4)0.0142 (2)0.0546 (3)0.0152 (2)
Cl20.0784 (3)0.0921 (3)0.0749 (3)0.0089 (2)0.0293 (2)0.0005 (2)
Geometric parameters (Å, º) top
N1—N21.357 (2)C16—C171.375 (2)
N1—C51.370 (2)C16—H160.9300
N1—C111.408 (2)C17—H170.9300
N2—C31.327 (2)C31—C361.391 (2)
C3—C41.418 (2)C31—C321.398 (2)
C3—C311.460 (2)C32—C331.369 (2)
C4—C51.346 (3)C32—H320.9300
C4—H40.9300C33—C341.384 (2)
C5—H50.9300C33—H330.9300
C11—C1A1.351 (2)C34—C351.382 (2)
C11—C121.474 (2)C34—Cl21.7366 (18)
C12—C171.392 (2)C35—C361.375 (2)
C12—C131.399 (2)C35—H350.9300
C13—C141.374 (2)C36—H360.9300
C13—H130.9300C1A—C2A1.431 (3)
C14—C151.384 (2)C1A—H1A0.9300
C14—H140.9300C2A—O11.219 (2)
C15—C161.387 (2)C2A—H2A1.07 (2)
C15—Cl11.7313 (17)
N2—N1—C5111.32 (14)C17—C16—H16120.5
N2—N1—C11120.54 (13)C15—C16—H16120.5
C5—N1—C11127.88 (15)C16—C17—C12121.30 (13)
C3—N2—N1105.24 (13)C16—C17—H17119.3
N2—C3—C4110.62 (16)C12—C17—H17119.3
N2—C3—C31120.42 (14)C36—C31—C32117.70 (16)
C4—C3—C31128.96 (15)C36—C31—C3121.53 (14)
C5—C4—C3105.75 (15)C32—C31—C3120.75 (14)
C5—C4—H4127.1C33—C32—C31121.34 (15)
C3—C4—H4127.1C33—C32—H32119.3
C4—C5—N1107.06 (16)C31—C32—H32119.3
C4—C5—H5126.5C32—C33—C34119.49 (15)
N1—C5—H5126.5C32—C33—H33120.3
C1A—C11—N1119.59 (16)C34—C33—H33120.3
C1A—C11—C12125.45 (15)C35—C34—C33120.66 (16)
N1—C11—C12114.95 (13)C35—C34—Cl2120.04 (13)
C17—C12—C13118.47 (15)C33—C34—Cl2119.29 (13)
C17—C12—C11120.65 (13)C36—C35—C34119.15 (15)
C13—C12—C11120.88 (14)C36—C35—H35120.4
C14—C13—C12120.84 (15)C34—C35—H35120.4
C14—C13—H13119.6C35—C36—C31121.60 (15)
C12—C13—H13119.6C35—C36—H36119.2
C13—C14—C15119.37 (14)C31—C36—H36119.2
C13—C14—H14120.3C11—C1A—C2A123.32 (17)
C15—C14—H14120.3C11—C1A—H1A118.3
C14—C15—C16121.07 (15)C2A—C1A—H1A118.3
C14—C15—Cl1119.74 (12)O1—C2A—C1A123.47 (19)
C16—C15—Cl1119.20 (13)O1—C2A—H2A119.7 (13)
C17—C16—C15118.93 (15)C1A—C2A—H2A116.7 (13)
C5—N1—N2—C30.51 (16)C14—C15—C16—C171.3 (2)
C11—N1—N2—C3175.14 (12)Cl1—C15—C16—C17178.47 (11)
N1—N2—C3—C40.49 (16)C15—C16—C17—C120.5 (2)
N1—N2—C3—C31179.66 (12)C13—C12—C17—C160.7 (2)
N2—C3—C4—C50.30 (18)C11—C12—C17—C16178.87 (13)
C31—C3—C4—C5179.86 (14)N2—C3—C31—C36175.27 (13)
C3—C4—C5—N10.03 (18)C4—C3—C31—C364.6 (2)
N2—N1—C5—C40.34 (18)N2—C3—C31—C323.1 (2)
C11—N1—C5—C4174.48 (14)C4—C3—C31—C32177.04 (15)
N2—N1—C11—C1A16.7 (2)C36—C31—C32—C332.1 (2)
C5—N1—C11—C1A156.99 (16)C3—C31—C32—C33176.38 (14)
N2—N1—C11—C12164.21 (12)C31—C32—C33—C340.4 (2)
C5—N1—C11—C1222.1 (2)C32—C33—C34—C351.9 (2)
C1A—C11—C12—C1752.2 (2)C32—C33—C34—Cl2176.72 (12)
N1—C11—C12—C17126.86 (15)C33—C34—C35—C362.4 (2)
C1A—C11—C12—C13128.27 (18)Cl2—C34—C35—C36176.17 (11)
N1—C11—C12—C1352.66 (19)C34—C35—C36—C310.7 (2)
C17—C12—C13—C141.0 (2)C32—C31—C36—C351.5 (2)
C11—C12—C13—C14178.48 (14)C3—C31—C36—C35176.91 (13)
C12—C13—C14—C150.3 (2)N1—C11—C1A—C2A173.32 (15)
C13—C14—C15—C160.9 (2)C12—C11—C1A—C2A7.7 (3)
C13—C14—C15—Cl1178.85 (12)C11—C1A—C2A—O1170.98 (18)
Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the C31–C36 ring.
D—H···AD—HH···AD···AD—H···A
C13—H13···Cl2i0.932.933.6447 (16)134
C14—H14···O1ii0.932.493.407 (2)167
C36—H36···Cl1iii0.932.903.6334 (16)137
C17—H17···Cg1iv0.932.683.4919 (18)147
Symmetry codes: (i) x, y, z+1; (ii) x1, y, z; (iii) x, y, z+2; (iv) x+1, y, z+2.

Experimental details

Crystal data
Chemical formulaC18H12Cl2N2O
Mr343.20
Crystal system, space groupTriclinic, 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)
V3)801.38 (9)
Z2
Radiation typeMo Kα
µ (mm1)0.41
Crystal size (mm)0.16 × 0.14 × 0.12
Data collection
DiffractometerBruker SMART APEX CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2001)
Tmin, Tmax0.884, 0.993
No. of measured, independent and
observed [I > 2σ(I)] reflections
8950, 3464, 2982
Rint0.018
(sin θ/λ)max1)0.639
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.040, 0.116, 1.04
No. of reflections3464
No. of parameters211
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)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···AD—HH···AD···AD—H···A
C13—H13···Cl2i0.932.933.6447 (16)134.3
C14—H14···O1ii0.932.493.407 (2)167.4
C36—H36···Cl1iii0.932.903.6334 (16)137.2
C17—H17···Cg1iv0.932.683.4919 (18)147
Symmetry codes: (i) x, y, z+1; (ii) x1, 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.

References

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