(Z)-1,2-Dichloro-1,2-bis­(3-chloro­quinoxalin-2-yl)ethene

Fun, H.-K.; Goh, J.H.; Maity, A.C.; Goswami, S.

doi:10.1107/S1600536810054322

organic compounds

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ISSN: 2056-9890

Volume 67| Part 2| February 2011| Page o290

doi:10.1107/S1600536810054322

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(Z)-1,2-Dichloro-1,2-bis(3-chloroquinoxalin-2-yl)ethene

Hoong-Kun Fun,^a ^*‡ Jia Hao Goh,^a § Annada C. Maity ^b and Shyamaprosad Goswami ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bDepartment of Chemistry, Bengal Engineering and Science University, Shibpur, Howrah 711 103, India
^*Correspondence e-mail: hkfun@usm.my

(Received 20 December 2010; accepted 26 December 2010; online 8 January 2011)

The title compound, C₁₈H₈Cl₄N₄, exists in a cis configuration with respect to the bridging C=C bond. The two essentially planar quinoxaline ring systems [maximum deviations = 0.012 (1) and 0.022 (1) Å] are inclined at an angle of 59.84 (3). In the crystal, adjacent molecules are linked into chains propagating along [001] via intermolecular C—H⋯N hydrogen bonds. Weak intermolecular π–π [centroid–centroid distance = 3.6029 (7)°] and C—H⋯π interactions are also observed.

Related literature

For general background to and applications of the title compound, see: Fun et al. (2009 ); Goswami et al. (2007 ). For closely related structures, see: Fun et al. (2009); Goswami et al. (2007). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₁₈H₈Cl₄N₄
M_r = 422.08
Monoclinic, P 2₁ /c
a = 19.0972 (5) Å
b = 10.9883 (3) Å
c = 8.1905 (2) Å
β = 90.782 (1)°
V = 1718.58 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.70 mm⁻¹
T = 100 K
0.79 × 0.22 × 0.10 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.608, T_max = 0.933
72483 measured reflections
8778 independent reflections
6556 reflections with I > 2σ(I)
R_int = 0.061

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.119
S = 1.11
8778 reflections
267 parameters
All H-atom parameters refined
Δρ_max = 0.59 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C13–C18 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17⋯N2ⁱ	0.995 (17)	2.454 (17)	3.2609 (16)	137.8 (13)
C16—H16⋯Cg1ⁱⁱ	0.97 (2)	3.00 (2)	3.9664 (16)	176.0 (16)
Symmetry codes: (i) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810054322/sj5082sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810054322/sj5082Isup2.hkl

checkCIF report

Comment top

Halogen substituted heterocyclic compounds are of great importance due to their broad spectrum of use in organic chemistry. Recently a series of trichloromethyl substituted heterocyclic compounds have been synthesized by us in good yield using N-chlorosuccinimide (NCS) and triphenylphosphine (PPh₃) in carbon tetrachloride (Fun et al., 2009; Goswami et al., 2007). Here we report the results of X-ray crystallographic studies of the supramolecular self-assembly of a chlorine-substituted heterocyclic compound to show its possible choice of polymer formation by self-assembly. Reaction of 2-chloro-3-trichloromethylquinoxaline with Co(I)(PPh₃)₃Cl results in the formation of the title compound.

The title compound (Fig. 1) exists in a cis configuration with respect to the bridging C9═C10 bond [bond length of C9═C10 = 1.3374 (16) Å and torsion angle of C8–C9–C10–C11 = -0.3 (2)°]. The two quinoxaline ring systems [(C1–C8/N1/N2) & (C11–C18/N3/N4)] are essentially planar, with maximum deviations of 0.022 (1) Å at atom C8 and -0.012 (1) Å at atom C11, respectively. An interplanar angle of 59.84 (3)° is formed between the two quinoxaline ring systems, indicating the molecule is not planar. All geometric parameters are consistent to those observed in closely related structures (Goswami et al., 2007; Fun et al., 2009).

In the crystal packing, intermolecular C17—H17···N2 hydrogen bonds (Table 1) link adjacent molecules into one-dimensional chains in an anti-parallel manner along the c axis (Fig. 2). Further stabilization of the crystal packing is provided by weak intermolecular C16—H16···Cg1 interactions (Table 1) as well as intermolecular Cg2···Cg3 interactions [3.6029 (7) Å; symmetry code: x, -y+3/2, z-1/2] where Cg1, Cg2 are the centroids of the C13–C18 and C1–C6 benzene rings, respectively, and Cg3 is the centroid of C1/C6–C8/N1/N2 pyrazine ring.

Related literature top

For general background to and applications of the title compound, see: Fun et al. (2009); Goswami et al. (2007). For closely related structures, see: Fun et al. (2009); Goswami et al. (2007). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

2-Chloro-3-trichloromethylquinoxaline (1 mmol) was dissolved in dry benzene (30 ml). The anhydrous green coloured Co(I)(PPh₃)₃Cl (2.5 mmol) catalyst was added to the reaction mixture with stirring at room temperature under nitrogen atmosphere. After 30 minutes, the colour of the reaction mixture changed from green to blue. The reaction mixture was then heated under reflux condition for 2-3 h. The solvent was evaporated to dryness. The residue was then worked up with water and the organic part was extracted with chloroform. The organic layer was dried (Na₂SO₄) and concentrated. Column chromatography of the crude product on silica gel and elution with methanol in chloroform afforded the title compound. Single crystals were grown by slow evaporation of a 1:1 solution of CHCl₃ and methanol.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids for non-H atoms and the atom-numbering scheme.
	Fig. 2. The crystal structure of the title compound, viewed along the b axis, showing a pair of 1D chains propagating along the c axis. Intermolecular hydrogen bonds are shown as dashed lines.

(Z)-1,2-Dichloro-1,2-bis(3-chloroquinoxalin-2-yl)ethene top

Crystal data top

C₁₈H₈Cl₄N₄	F(000) = 848
M_r = 422.08	D_x = 1.631 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9887 reflections
a = 19.0972 (5) Å	θ = 2.1–37.2°
b = 10.9883 (3) Å	µ = 0.70 mm⁻¹
c = 8.1905 (2) Å	T = 100 K
β = 90.782 (1)°	Block, yellow
V = 1718.58 (8) Å³	0.79 × 0.22 × 0.10 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	8778 independent reflections
Radiation source: fine-focus sealed tube	6556 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.061
ϕ and ω scans	θ_max = 37.2°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −32→32
T_min = 0.608, T_max = 0.933	k = −18→18
72483 measured reflections	l = −13→13

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.119	All H-atom parameters refined
S = 1.11	w = 1/[σ²(F_o²) + (0.060P)² + 0.1538P] where P = (F_o² + 2F_c²)/3
8778 reflections	(Δ/σ)_max = 0.001
267 parameters	Δρ_max = 0.59 e Å⁻³
0 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

C₁₈H₈Cl₄N₄	V = 1718.58 (8) Å³
M_r = 422.08	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 19.0972 (5) Å	µ = 0.70 mm⁻¹
b = 10.9883 (3) Å	T = 100 K
c = 8.1905 (2) Å	0.79 × 0.22 × 0.10 mm
β = 90.782 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	8778 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	6556 reflections with I > 2σ(I)
T_min = 0.608, T_max = 0.933	R_int = 0.061
72483 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.119	All H-atom parameters refined
S = 1.11	Δρ_max = 0.59 e Å⁻³
8778 reflections	Δρ_min = −0.35 e Å⁻³
267 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1)K.

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 > 2sigma(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
Cl1	0.230183 (15)	0.56482 (3)	−0.19687 (4)	0.01973 (7)
Cl2	0.408666 (15)	0.33929 (3)	−0.01835 (4)	0.02087 (7)
Cl3	0.277057 (17)	0.19701 (3)	0.08651 (5)	0.02505 (8)
Cl4	0.139656 (17)	0.28579 (3)	−0.12100 (4)	0.02431 (7)
N1	0.39159 (5)	0.59732 (9)	0.11036 (12)	0.01616 (17)
N2	0.30364 (5)	0.74383 (9)	−0.08414 (12)	0.01681 (17)
N3	0.21167 (5)	0.49059 (9)	0.24250 (12)	0.01686 (17)
N4	0.08344 (5)	0.42781 (9)	0.09017 (13)	0.01902 (19)
C1	0.40036 (6)	0.72039 (10)	0.10598 (14)	0.01538 (19)
C2	0.45443 (6)	0.77568 (11)	0.20007 (15)	0.0180 (2)
C3	0.46254 (7)	0.89969 (11)	0.19571 (16)	0.0202 (2)
C4	0.41789 (7)	0.97290 (11)	0.09745 (16)	0.0205 (2)
C5	0.36555 (7)	0.92203 (10)	0.00467 (15)	0.0181 (2)
C6	0.35580 (6)	0.79460 (10)	0.00883 (14)	0.01560 (19)
C7	0.29618 (6)	0.62669 (10)	−0.07490 (14)	0.01589 (19)
C8	0.33959 (6)	0.55012 (10)	0.02467 (14)	0.01502 (18)
C9	0.33274 (6)	0.41522 (10)	0.03069 (15)	0.01644 (19)
C10	0.27542 (6)	0.35370 (10)	0.07344 (15)	0.0173 (2)
C11	0.20886 (6)	0.41146 (10)	0.12282 (14)	0.01590 (19)
C12	0.14274 (6)	0.38222 (10)	0.04606 (14)	0.0173 (2)
C13	0.08526 (6)	0.50918 (11)	0.21677 (15)	0.0181 (2)
C14	0.02225 (7)	0.56163 (13)	0.26997 (17)	0.0240 (2)
C15	0.02406 (8)	0.64421 (14)	0.39522 (19)	0.0281 (3)
C16	0.08807 (8)	0.67632 (13)	0.47183 (19)	0.0275 (3)
C17	0.15010 (7)	0.62649 (12)	0.42128 (16)	0.0230 (2)
C18	0.14972 (6)	0.54162 (10)	0.29197 (14)	0.01708 (19)
H2	0.4818 (9)	0.7241 (16)	0.265 (2)	0.026 (4)*
H3	0.4954 (10)	0.9394 (17)	0.253 (2)	0.039 (5)*
H4	0.4232 (9)	1.0550 (17)	0.094 (2)	0.028 (5)*
H5	0.3373 (9)	0.9670 (16)	−0.066 (2)	0.027 (4)*
H14	−0.0216 (9)	0.5407 (16)	0.215 (2)	0.030 (5)*
H15	−0.0164 (12)	0.6781 (18)	0.435 (3)	0.041 (6)*
H16	0.0870 (10)	0.7361 (18)	0.559 (3)	0.035 (5)*
H17	0.1949 (9)	0.6476 (16)	0.478 (2)	0.026 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.01985 (13)	0.01898 (12)	0.02025 (13)	−0.00230 (9)	−0.00389 (10)	0.00064 (9)
Cl2	0.01669 (12)	0.01806 (12)	0.02796 (15)	0.00393 (9)	0.00359 (10)	0.00006 (10)
Cl3	0.02286 (14)	0.01315 (12)	0.03931 (18)	0.00158 (9)	0.00726 (12)	0.00199 (11)
Cl4	0.02400 (14)	0.02459 (14)	0.02439 (15)	−0.00171 (11)	0.00284 (11)	−0.00901 (11)
N1	0.0155 (4)	0.0167 (4)	0.0163 (4)	0.0010 (3)	0.0017 (3)	0.0000 (3)
N2	0.0176 (4)	0.0160 (4)	0.0169 (4)	−0.0001 (3)	0.0009 (3)	0.0005 (3)
N3	0.0165 (4)	0.0152 (4)	0.0190 (4)	0.0001 (3)	0.0029 (3)	0.0008 (3)
N4	0.0170 (4)	0.0209 (4)	0.0192 (5)	0.0002 (3)	0.0011 (4)	−0.0016 (4)
C1	0.0148 (4)	0.0158 (4)	0.0155 (5)	0.0010 (3)	0.0024 (4)	0.0005 (3)
C2	0.0162 (5)	0.0204 (5)	0.0174 (5)	0.0008 (4)	−0.0001 (4)	−0.0016 (4)
C3	0.0189 (5)	0.0204 (5)	0.0213 (5)	−0.0033 (4)	0.0009 (4)	−0.0026 (4)
C4	0.0230 (6)	0.0158 (5)	0.0227 (6)	−0.0016 (4)	0.0030 (4)	−0.0008 (4)
C5	0.0205 (5)	0.0151 (4)	0.0186 (5)	0.0011 (4)	0.0015 (4)	0.0007 (4)
C6	0.0145 (4)	0.0163 (4)	0.0161 (5)	0.0006 (3)	0.0022 (4)	−0.0002 (3)
C7	0.0149 (4)	0.0167 (4)	0.0161 (5)	0.0007 (3)	0.0005 (4)	0.0007 (4)
C8	0.0145 (4)	0.0149 (4)	0.0157 (5)	0.0013 (3)	0.0021 (4)	0.0007 (3)
C9	0.0158 (5)	0.0145 (4)	0.0190 (5)	0.0017 (3)	0.0018 (4)	0.0005 (4)
C10	0.0171 (5)	0.0139 (4)	0.0210 (5)	0.0012 (3)	0.0027 (4)	0.0008 (4)
C11	0.0158 (5)	0.0137 (4)	0.0183 (5)	0.0005 (3)	0.0028 (4)	0.0016 (3)
C12	0.0183 (5)	0.0164 (5)	0.0174 (5)	−0.0004 (4)	0.0019 (4)	−0.0017 (4)
C13	0.0181 (5)	0.0189 (5)	0.0172 (5)	0.0021 (4)	0.0012 (4)	0.0001 (4)
C14	0.0178 (5)	0.0288 (6)	0.0255 (6)	0.0051 (4)	0.0014 (5)	−0.0020 (5)
C15	0.0243 (6)	0.0317 (7)	0.0286 (7)	0.0078 (5)	0.0054 (5)	−0.0047 (5)
C16	0.0282 (7)	0.0267 (6)	0.0280 (7)	0.0018 (5)	0.0068 (5)	−0.0085 (5)
C17	0.0221 (6)	0.0228 (5)	0.0241 (6)	−0.0016 (4)	0.0024 (5)	−0.0059 (5)
C18	0.0177 (5)	0.0157 (4)	0.0179 (5)	0.0007 (4)	0.0021 (4)	−0.0003 (4)

Geometric parameters (Å, º) top

Cl1—C7	1.7362 (11)	C4—H4	0.908 (18)
Cl2—C9	1.7250 (12)	C5—C6	1.4130 (15)
Cl3—C10	1.7253 (11)	C5—H5	0.927 (18)
Cl4—C12	1.7310 (12)	C7—C8	1.4289 (15)
N1—C8	1.3149 (15)	C8—C9	1.4889 (15)
N1—C1	1.3632 (14)	C9—C10	1.3374 (16)
N2—C7	1.2974 (15)	C10—C11	1.4819 (16)
N2—C6	1.3646 (15)	C11—C12	1.4393 (16)
N3—C11	1.3108 (15)	C13—C14	1.4086 (17)
N3—C18	1.3754 (15)	C13—C18	1.4146 (17)
N4—C12	1.2941 (16)	C14—C15	1.370 (2)
N4—C13	1.3692 (16)	C14—H14	0.974 (18)
C1—C6	1.4156 (15)	C15—C16	1.411 (2)
C1—C2	1.4169 (16)	C15—H15	0.92 (2)
C2—C3	1.3720 (17)	C16—C17	1.3739 (19)
C2—H2	0.934 (18)	C16—H16	0.97 (2)
C3—C4	1.4153 (18)	C17—C18	1.4111 (17)
C3—H3	0.89 (2)	C17—H17	0.994 (18)
C4—C5	1.3669 (17)

C8—N1—C1	117.99 (10)	C10—C9—Cl2	120.67 (9)
C7—N2—C6	116.94 (10)	C8—C9—Cl2	113.54 (8)
C11—N3—C18	117.65 (10)	C9—C10—C11	124.28 (10)
C12—N4—C13	116.81 (10)	C9—C10—Cl3	120.43 (9)
N1—C1—C6	120.87 (10)	C11—C10—Cl3	115.17 (8)
N1—C1—C2	119.99 (10)	N3—C11—C12	120.10 (10)
C6—C1—C2	119.13 (10)	N3—C11—C10	117.49 (10)
C3—C2—C1	119.56 (11)	C12—C11—C10	122.40 (10)
C3—C2—H2	123.7 (11)	N4—C12—C11	123.88 (11)
C1—C2—H2	116.7 (11)	N4—C12—Cl4	115.93 (9)
C2—C3—C4	120.80 (11)	C11—C12—Cl4	120.14 (9)
C2—C3—H3	123.4 (12)	N4—C13—C14	119.24 (11)
C4—C3—H3	115.8 (12)	N4—C13—C18	120.48 (11)
C5—C4—C3	120.93 (11)	C14—C13—C18	120.27 (11)
C5—C4—H4	118.1 (11)	C15—C14—C13	119.33 (12)
C3—C4—H4	121.0 (11)	C15—C14—H14	121.1 (11)
C4—C5—C6	119.17 (11)	C13—C14—H14	119.5 (11)
C4—C5—H5	122.9 (11)	C14—C15—C16	120.76 (13)
C6—C5—H5	117.9 (11)	C14—C15—H15	121.1 (13)
N2—C6—C5	119.15 (10)	C16—C15—H15	118.0 (13)
N2—C6—C1	120.45 (10)	C17—C16—C15	120.76 (13)
C5—C6—C1	120.40 (10)	C17—C16—H16	121.3 (11)
N2—C7—C8	123.65 (10)	C15—C16—H16	117.9 (11)
N2—C7—Cl1	115.75 (8)	C16—C17—C18	119.60 (12)
C8—C7—Cl1	120.58 (8)	C16—C17—H17	120.4 (10)
N1—C8—C7	120.03 (10)	C18—C17—H17	120.0 (10)
N1—C8—C9	116.17 (10)	N3—C18—C17	119.66 (11)
C7—C8—C9	123.69 (10)	N3—C18—C13	121.06 (10)
C10—C9—C8	125.76 (10)	C17—C18—C13	119.27 (11)

C8—N1—C1—C6	−1.53 (16)	C8—C9—C10—Cl3	−176.06 (9)
C8—N1—C1—C2	178.18 (11)	Cl2—C9—C10—Cl3	2.01 (15)
N1—C1—C2—C3	−179.56 (11)	C18—N3—C11—C12	1.06 (16)
C6—C1—C2—C3	0.15 (17)	C18—N3—C11—C10	−178.07 (10)
C1—C2—C3—C4	−0.48 (19)	C9—C10—C11—N3	−54.58 (17)
C2—C3—C4—C5	0.10 (19)	Cl3—C10—C11—N3	121.43 (10)
C3—C4—C5—C6	0.62 (19)	C9—C10—C11—C12	126.31 (13)
C7—N2—C6—C5	−179.23 (11)	Cl3—C10—C11—C12	−57.69 (14)
C7—N2—C6—C1	1.88 (16)	C13—N4—C12—C11	0.56 (17)
C4—C5—C6—N2	−179.84 (11)	C13—N4—C12—Cl4	−176.74 (9)
C4—C5—C6—C1	−0.94 (18)	N3—C11—C12—N4	−1.63 (18)
N1—C1—C6—N2	−0.85 (17)	C10—C11—C12—N4	177.46 (11)
C2—C1—C6—N2	179.44 (11)	N3—C11—C12—Cl4	175.56 (9)
N1—C1—C6—C5	−179.73 (11)	C10—C11—C12—Cl4	−5.35 (16)
C2—C1—C6—C5	0.56 (17)	C12—N4—C13—C14	−179.97 (12)
C6—N2—C7—C8	−0.66 (17)	C12—N4—C13—C18	0.90 (17)
C6—N2—C7—Cl1	−179.12 (9)	N4—C13—C14—C15	−179.18 (13)
C1—N1—C8—C7	2.74 (16)	C18—C13—C14—C15	−0.05 (19)
C1—N1—C8—C9	178.96 (10)	C13—C14—C15—C16	−0.5 (2)
N2—C7—C8—N1	−1.74 (18)	C14—C15—C16—C17	0.7 (2)
Cl1—C7—C8—N1	176.65 (9)	C15—C16—C17—C18	−0.4 (2)
N2—C7—C8—C9	−177.66 (11)	C11—N3—C18—C17	179.47 (11)
Cl1—C7—C8—C9	0.73 (16)	C11—N3—C18—C13	0.36 (16)
N1—C8—C9—C10	124.93 (13)	C16—C17—C18—N3	−179.24 (12)
C7—C8—C9—C10	−59.01 (18)	C16—C17—C18—C13	−0.11 (19)
N1—C8—C9—Cl2	−53.26 (13)	N4—C13—C18—N3	−1.41 (18)
C7—C8—C9—Cl2	122.81 (11)	C14—C13—C18—N3	179.47 (11)
C8—C9—C10—C11	−0.3 (2)	N4—C13—C18—C17	179.47 (11)
Cl2—C9—C10—C11	177.81 (9)	C14—C13—C18—C17	0.35 (18)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C13–C18 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···N2ⁱ	0.995 (17)	2.454 (17)	3.2609 (16)	137.8 (13)
C16—H16···Cg1ⁱⁱ	0.97 (2)	3.00 (2)	3.9664 (16)	176.0 (16)

Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) x, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₈H₈Cl₄N₄
M_r	422.08
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	19.0972 (5), 10.9883 (3), 8.1905 (2)
β (°)	90.782 (1)
V (Å³)	1718.58 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.70
Crystal size (mm)	0.79 × 0.22 × 0.10

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.608, 0.933
No. of measured, independent and observed [I > 2σ(I)] reflections	72483, 8778, 6556
R_int	0.061
(sin θ/λ)_max (Å⁻¹)	0.851

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.119, 1.11
No. of reflections	8778
No. of parameters	267
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.59, −0.35

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C13–C18 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···N2ⁱ	0.995 (17)	2.454 (17)	3.2609 (16)	137.8 (13)
C16—H16···Cg1ⁱⁱ	0.97 (2)	3.00 (2)	3.9664 (16)	176.0 (16)

Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) x, −y+1/2, z−1/2.

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

§Thomson Reuters ResearcherID: C-7576-2009.

Acknowledgements

HKF and JHG thank USM for the Research University Grant (No. 1001/PFIZIK/811160). ACM and SG thank the DST, Government of India [SR/S1/OC-13/2005] for financial support. ACM also thanks the UGC, Government of India, for a fellowship.

References

Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107. CrossRef CAS Web of Science IUCr Journals Google Scholar
Fun, H.-K., Kia, R., Maity, A. C., Chakrabarty, R. & Goswami, S. (2009). Acta Cryst. E65, o354. Web of Science CSD CrossRef IUCr Journals Google Scholar
Goswami, S., Maity, A. C. & Fun, H.-K. (2007). Chem. Lett. 36, 552–553 Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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