[2-(1H-Benzimidazol-2-yl-κN3)aniline-κN]dichloridozinc

Eltayeb, N.E.; Teoh, S.G.; Chantrapromma, S.; Fun, H.-K.

doi:10.1107/S1600536811026572

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 8| August 2011| Pages m1062-m1063

doi:10.1107/S1600536811026572

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[2-(1H-Benzimidazol-2-yl-κN³)aniline-κN]dichloridozinc

Naser Eltaher Eltayeb,^a,^b Siang Guan Teoh,^a Suchada Chantrapromma ^c ‡ and Hoong-Kun Fun ^d ^*§

^aSchool of Chemical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bDepartment of Chemistry, Faculty of Pure and Applied Sciences, International University of Africa, Sudan, ^cCrystal Materials Research Unit, Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, and ^dX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: hkfun@usm.my

(Received 1 July 2011; accepted 4 July 2011; online 9 July 2011)

In the title benzimidazole mononuclear complex, [ZnCl₂(C₁₃H₁₁N₃)], the Zn^II ion is four-coordinated in a distorted tetrahedral geometry by an imidazole N, an amino N and two Cl atoms. The dihedral angle between the benzimidazole and benzene rings is 9.57 (1)°. In the crystal, molecules are linked by weak N—H⋯Cl hydrogen bonds into layers parallel to the bc plane. π–π interactions with centroid–centroid distances in the range 3.4452 (8)–3.8074 (8) Å are also observed.

Related literature

For bond-length data, see: Allen et al. (1987 ). For background to benzimidazoles and their applications, see: Chassaing et al. (2008 ); Podunavac-Kuzmonovic et al. (1999 ); Xue et al. (2011 ). For related structures, see: Eltayeb et al. (2007 ; 2009 ; 2011 ); Maldonado-Rogado et al. (2007 ). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

[ZnCl₂(C₁₃H₁₁N₃)]
M_r = 345.54
Monoclinic, C 2/c
a = 22.0252 (7) Å
b = 10.0651 (3) Å
c = 15.3676 (6) Å
β = 125.244 (2)°
V = 2782.32 (18) Å³
Z = 8
Mo Kα radiation
μ = 2.14 mm⁻¹
T = 100 K
0.48 × 0.31 × 0.31 mm

Data collection

Bruker APEX DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.428, T_max = 0.560
50659 measured reflections
7344 independent reflections
5887 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.027
wR(F²) = 0.081
S = 1.02
7344 reflections
172 parameters
H-atom parameters constrained
Δρ_max = 0.54 e Å⁻³
Δρ_min = −0.55 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯Cl1ⁱ	0.82	2.56	3.3503 (9)	164
N3—H1N3⋯Cl1ⁱⁱ	0.89	2.49	3.3753 (9)	174
N3—H2N3⋯Cl2ⁱⁱⁱ	0.94	2.44	3.3015 (12)	153
Symmetry codes: (i) -x, -y+1, -z; (ii) -x, -y+2, -z; (iii) $[-x, y, -z+{\script{1\over 2}}]$ .

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/S1600536811026572/rz2622sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811026572/rz2622Isup2.hkl

checkCIF report

Comment top

Benzimidazole compounds have a wide range of biological properties such as antibacterial (Chassaing et al., 2008) and inhibitory activity against enteroviruses (Xue et al., 2011). The complexes of transition metal salts with benzimidazole derivatives have been extensively studied as models of some important biological molecules (Podunavac-Kuzmonovic et al., 1999). As part of our ongoing structural studies of benzimidazoles (Eltayeb et al., 2007; 2009; 2011) and as an extension of investigation on their complexes, the title zinc(II) complex, (I), is reported here.

Complex (I) is a mononuclear zinc(II) complex (Fig. 1) in which the coordination geometry around the zinc ion is distorted tetrahedral, with the metal four-coordinated by an imidazole N, an amino N and two Cl atoms. In the complex, the 2-(2-aminophenyl)-1H-benzimidazole acts as a bidentate ligand. The bond angles around the central metal zinc(II) show some deviations from ideal tetrahedral geometry [N3-Zn1-Cl1 = 109.27 (3)°, N1-Zn1-Cl2= 114.83 (3)°, Cl1-Zn1-Cl2 = 117.844 (13)° and the bite angle N1–Zn1-N3 = 89.36 (3)°]. The Zn-N [2.0068 (8) and 2.0471 (9) Å] and Zn-Cl [2.2041 (3) and 2.2589 (3) Å] bond lengths are comparable to those found in a similar zinc(II) benzimidazole complex (Maldonado-Rogado et al., 2007). The benzimidazole ring system (C1–C7/N1–N2) is planar (r.m.s. of 0.0097 (1) Å), the larger deviation being observed for atom C1 (0.019 (1) Å). The dihedral angle between the benzimidazole and phenyl rings is 9.57 (6)°. The bond lengths of ligand are within normal ranges (Allen et al., 1987).

In the crystal structure (Fig. 2), the molecules are linked through N—H···Cl hydrogen bonds into two dimensional layers parallel to the bc plane. π···π interactions are observed with centroid···centroid distances: Cg₁···Cg₁ⁱⁱⁱ = 3.4452 (8)) Å, Cg₁···Cg₂ⁱⁱⁱ = 3.6879 (9) Å and Cg₂···Cg₃ⁱ = 3.8074 (8) Å (Cg₁, Cg₂ and Cg₃ are the centroids of the C1/C6–C7/N1–N2, C1–C6 and C8–C13 rings, respectively; symmetry codes: (i) -x, 1-y, -z; (iii) -x, y, 1/2-z).

Related literature top

For bond-length data, see: Allen et al. (1987). For background to benzimidazoles and their applications, see: Chassaing et al. (2008); Podunavac-Kuzmonovic et al. (1999); Xue et al. (2011). For related structures, see: Eltayeb et al. (2007; 2009; 2011); Maldonado-Rogado et al. (2007). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

The title compound was synthesized by adding 2-hydroxy-3-methylbenzaldehyde (0.136 g, 1.0 mmol) to a solution of 2-(2-aminophenyl)-1H-benzimidazole (0.209 g, 1.0 mmol) in ethanol (30 mL). The colour of the resulting solution was pale-yellow. Then upon addition of zinc chloride (0.136 g, 1.0 mmol), the colour of the solution became golden-yellow. The mixture was refluxed with stirring for 3 h. The resultant solution was filtered and the filtrate was evaporated to give a yellow solid product. Yellow block-shaped single crystals of the title compound suitable for X-ray structure determination were obtained by slow evaporation of an ethanol solution at room temperature after several days.

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, with 50% probability displacement ellipsoids.
	Fig. 2. The crystal packing of the title compound viewed down the b axis. Hydrogen bonds are shown as dashed lines.

[2-(1H-Benzimidazol-2-yl-κN³)aniline- κN]dichloridozinc top

Crystal data top

[ZnCl₂(C₁₃H₁₁N₃)]	F(000) = 1392
M_r = 345.54	D_x = 1.650 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 7344 reflections
a = 22.0252 (7) Å	θ = 2.3–37.7°
b = 10.0651 (3) Å	µ = 2.14 mm⁻¹
c = 15.3676 (6) Å	T = 100 K
β = 125.244 (2)°	Block, yellow
V = 2782.32 (18) Å³	0.48 × 0.31 × 0.31 mm
Z = 8

Data collection top

Bruker APEX DUO CCD area-detector diffractometer	7344 independent reflections
Radiation source: sealed tube	5887 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
ϕ and ω scans	θ_max = 37.7°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −37→36
T_min = 0.428, T_max = 0.560	k = −17→17
50659 measured reflections	l = −25→26

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)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.081	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0419P)² + 0.7801P] where P = (F_o² + 2F_c²)/3
7344 reflections	(Δ/σ)_max = 0.002
172 parameters	Δρ_max = 0.54 e Å⁻³
0 restraints	Δρ_min = −0.55 e Å⁻³

Crystal data top

[ZnCl₂(C₁₃H₁₁N₃)]	V = 2782.32 (18) Å³
M_r = 345.54	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 22.0252 (7) Å	µ = 2.14 mm⁻¹
b = 10.0651 (3) Å	T = 100 K
c = 15.3676 (6) Å	0.48 × 0.31 × 0.31 mm
β = 125.244 (2)°

Data collection top

Bruker APEX DUO CCD area-detector diffractometer	7344 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	5887 reflections with I > 2σ(I)
T_min = 0.428, T_max = 0.560	R_int = 0.023
50659 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.027	0 restraints
wR(F²) = 0.081	H-atom parameters constrained
S = 1.02	Δρ_max = 0.54 e Å⁻³
7344 reflections	Δρ_min = −0.55 e Å⁻³
172 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
Zn1	0.057453 (6)	0.825871 (11)	0.151068 (9)	0.03470 (4)
Cl1	0.094347 (18)	0.82859 (2)	0.04109 (2)	0.04377 (6)
Cl2	0.121812 (17)	0.94430 (3)	0.29852 (2)	0.04885 (7)
N1	0.03795 (5)	0.63755 (8)	0.17124 (6)	0.03277 (14)
N2	−0.01309 (5)	0.43948 (8)	0.11361 (7)	0.03566 (16)
H1N2	−0.0400	0.3776	0.0772	0.043*
N3	−0.05430 (5)	0.86317 (8)	0.06474 (7)	0.03630 (16)
H1N3	−0.0613	0.9453	0.0395	0.044*
H2N3	−0.0606	0.8661	0.1203	0.044*
C1	0.08602 (5)	0.54368 (9)	0.24599 (8)	0.03401 (16)
C2	0.15487 (6)	0.55968 (12)	0.34379 (9)	0.0441 (2)
H2A	0.1765	0.6429	0.3686	0.053*
C3	0.18917 (8)	0.44533 (15)	0.40179 (11)	0.0548 (3)
H3A	0.2351	0.4519	0.4673	0.066*
C4	0.15673 (9)	0.32000 (14)	0.36457 (13)	0.0578 (3)
H4A	0.1816	0.2457	0.4063	0.069*
C5	0.08893 (8)	0.30296 (12)	0.26782 (11)	0.0487 (3)
H5A	0.0677	0.2195	0.2428	0.058*
C6	0.05428 (6)	0.41848 (9)	0.20999 (8)	0.03638 (18)
C7	−0.02133 (5)	0.57180 (8)	0.09356 (7)	0.03092 (15)
C8	−0.08750 (5)	0.62967 (9)	−0.00210 (7)	0.03133 (15)
C9	−0.13949 (6)	0.54428 (11)	−0.08355 (9)	0.0409 (2)
H9A	−0.1313	0.4531	−0.0751	0.049*
C10	−0.20257 (7)	0.59227 (14)	−0.17600 (10)	0.0501 (3)
H10A	−0.2366	0.5336	−0.2286	0.060*
C11	−0.21502 (7)	0.72704 (15)	−0.19038 (10)	0.0556 (3)
H11A	−0.2567	0.7598	−0.2535	0.067*
C12	−0.16525 (7)	0.81339 (12)	−0.11062 (10)	0.0478 (3)
H12A	−0.1741	0.9043	−0.1203	0.057*
C13	−0.10222 (5)	0.76671 (9)	−0.01632 (7)	0.03314 (16)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.03589 (6)	0.02529 (5)	0.03528 (6)	−0.00291 (3)	0.01612 (5)	−0.00044 (3)
Cl1	0.05837 (16)	0.03021 (11)	0.04711 (13)	−0.00299 (9)	0.03297 (13)	0.00024 (8)
Cl2	0.05149 (15)	0.04321 (13)	0.04471 (13)	−0.01328 (11)	0.02364 (11)	−0.01315 (10)
N1	0.0341 (3)	0.0252 (3)	0.0324 (3)	−0.0009 (3)	0.0154 (3)	0.0028 (2)
N2	0.0392 (4)	0.0235 (3)	0.0404 (4)	−0.0010 (3)	0.0207 (3)	0.0010 (3)
N3	0.0372 (4)	0.0252 (3)	0.0366 (4)	0.0020 (3)	0.0156 (3)	−0.0006 (3)
C1	0.0358 (4)	0.0293 (4)	0.0345 (4)	0.0030 (3)	0.0188 (3)	0.0054 (3)
C2	0.0390 (5)	0.0421 (5)	0.0387 (5)	0.0026 (4)	0.0153 (4)	0.0045 (4)
C3	0.0460 (6)	0.0552 (7)	0.0454 (6)	0.0125 (5)	0.0162 (5)	0.0139 (5)
C4	0.0568 (7)	0.0461 (7)	0.0588 (7)	0.0189 (5)	0.0266 (6)	0.0219 (5)
C5	0.0541 (6)	0.0299 (4)	0.0586 (7)	0.0101 (4)	0.0306 (6)	0.0126 (4)
C6	0.0405 (4)	0.0275 (4)	0.0413 (4)	0.0039 (3)	0.0237 (4)	0.0055 (3)
C7	0.0345 (4)	0.0238 (3)	0.0331 (4)	−0.0006 (3)	0.0187 (3)	0.0011 (3)
C8	0.0316 (4)	0.0280 (3)	0.0313 (3)	−0.0009 (3)	0.0163 (3)	−0.0002 (3)
C9	0.0391 (5)	0.0345 (4)	0.0406 (5)	−0.0050 (4)	0.0180 (4)	−0.0065 (4)
C10	0.0374 (5)	0.0505 (6)	0.0421 (5)	−0.0056 (4)	0.0112 (4)	−0.0100 (5)
C11	0.0369 (5)	0.0533 (7)	0.0440 (6)	0.0034 (5)	0.0045 (4)	−0.0008 (5)
C12	0.0372 (5)	0.0385 (5)	0.0438 (5)	0.0061 (4)	0.0095 (4)	0.0038 (4)
C13	0.0307 (4)	0.0288 (4)	0.0334 (4)	0.0015 (3)	0.0147 (3)	0.0007 (3)

Geometric parameters (Å, º) top

Zn1—N1	2.0068 (8)	C3—H3A	0.9300
Zn1—N3	2.0471 (9)	C4—C5	1.381 (2)
Zn1—Cl2	2.2041 (3)	C4—H4A	0.9300
Zn1—Cl1	2.2589 (3)	C5—C6	1.3933 (14)
N1—C7	1.3300 (12)	C5—H5A	0.9300
N1—C1	1.3890 (12)	C7—C8	1.4668 (12)
N2—C7	1.3554 (12)	C8—C9	1.4009 (13)
N2—C6	1.3798 (13)	C8—C13	1.4049 (13)
N2—H1N2	0.8188	C9—C10	1.3797 (16)
N3—C13	1.4460 (12)	C9—H9A	0.9300
N3—H1N3	0.8877	C10—C11	1.376 (2)
N3—H2N3	0.9418	C10—H10A	0.9300
C1—C6	1.3916 (14)	C11—C12	1.3816 (18)
C1—C2	1.3978 (15)	C11—H11A	0.9300
C2—C3	1.3830 (17)	C12—C13	1.3878 (14)
C2—H2A	0.9300	C12—H12A	0.9300
C3—C4	1.399 (2)

N1—Zn1—N3	89.36 (3)	C3—C4—H4A	118.9
N1—Zn1—Cl2	114.83 (3)	C4—C5—C6	115.92 (12)
N3—Zn1—Cl2	112.74 (3)	C4—C5—H5A	122.0
N1—Zn1—Cl1	109.18 (3)	C6—C5—H5A	122.0
N3—Zn1—Cl1	109.27 (3)	N2—C6—C1	105.68 (8)
Cl2—Zn1—Cl1	117.844 (13)	N2—C6—C5	131.80 (10)
C7—N1—C1	106.79 (8)	C1—C6—C5	122.52 (10)
C7—N1—Zn1	121.20 (6)	N1—C7—N2	110.58 (8)
C1—N1—Zn1	129.89 (7)	N1—C7—C8	126.51 (8)
C7—N2—C6	108.33 (8)	N2—C7—C8	122.91 (8)
C7—N2—H1N2	130.1	C9—C8—C13	117.84 (9)
C6—N2—H1N2	121.5	C9—C8—C7	118.62 (9)
C13—N3—Zn1	116.24 (6)	C13—C8—C7	123.53 (8)
C13—N3—H1N3	113.1	C10—C9—C8	121.57 (10)
Zn1—N3—H1N3	107.2	C10—C9—H9A	119.2
C13—N3—H2N3	112.7	C8—C9—H9A	119.2
Zn1—N3—H2N3	99.8	C11—C10—C9	119.95 (10)
H1N3—N3—H2N3	106.7	C11—C10—H10A	120.0
N1—C1—C6	108.60 (8)	C9—C10—H10A	120.0
N1—C1—C2	130.32 (9)	C10—C11—C12	119.67 (11)
C6—C1—C2	121.07 (9)	C10—C11—H11A	120.2
C3—C2—C1	116.57 (11)	C12—C11—H11A	120.2
C3—C2—H2A	121.7	C11—C12—C13	121.13 (11)
C1—C2—H2A	121.7	C11—C12—H12A	119.4
C2—C3—C4	121.78 (12)	C13—C12—H12A	119.4
C2—C3—H3A	119.1	C12—C13—C8	119.79 (9)
C4—C3—H3A	119.1	C12—C13—N3	117.73 (9)
C5—C4—C3	122.13 (11)	C8—C13—N3	122.48 (8)
C5—C4—H4A	118.9

N3—Zn1—N1—C7	37.88 (8)	C4—C5—C6—C1	0.90 (19)
Cl2—Zn1—N1—C7	152.76 (7)	C1—N1—C7—N2	−1.27 (11)
Cl1—Zn1—N1—C7	−72.34 (8)	Zn1—N1—C7—N2	163.70 (7)
N3—Zn1—N1—C1	−160.99 (9)	C1—N1—C7—C8	178.98 (9)
Cl2—Zn1—N1—C1	−46.11 (10)	Zn1—N1—C7—C8	−16.04 (14)
Cl1—Zn1—N1—C1	88.79 (9)	C6—N2—C7—N1	1.11 (12)
N1—Zn1—N3—C13	−47.06 (7)	C6—N2—C7—C8	−179.14 (9)
Cl2—Zn1—N3—C13	−163.85 (6)	N1—C7—C8—C9	170.17 (10)
Cl1—Zn1—N3—C13	63.07 (7)	N2—C7—C8—C9	−9.55 (15)
C7—N1—C1—C6	0.96 (11)	N1—C7—C8—C13	−10.56 (16)
Zn1—N1—C1—C6	−162.24 (7)	N2—C7—C8—C13	169.73 (10)
C7—N1—C1—C2	−177.97 (12)	C13—C8—C9—C10	1.27 (17)
Zn1—N1—C1—C2	18.82 (17)	C7—C8—C9—C10	−179.41 (11)
N1—C1—C2—C3	178.91 (12)	C8—C9—C10—C11	0.9 (2)
C6—C1—C2—C3	0.09 (18)	C9—C10—C11—C12	−1.9 (2)
C1—C2—C3—C4	0.0 (2)	C10—C11—C12—C13	0.7 (2)
C2—C3—C4—C5	0.3 (3)	C11—C12—C13—C8	1.5 (2)
C3—C4—C5—C6	−0.8 (2)	C11—C12—C13—N3	−177.82 (13)
C7—N2—C6—C1	−0.46 (11)	C9—C8—C13—C12	−2.43 (16)
C7—N2—C6—C5	178.79 (13)	C7—C8—C13—C12	178.29 (11)
N1—C1—C6—N2	−0.30 (11)	C9—C8—C13—N3	176.84 (10)
C2—C1—C6—N2	178.75 (10)	C7—C8—C13—N3	−2.44 (15)
N1—C1—C6—C5	−179.64 (11)	Zn1—N3—C13—C12	−143.37 (10)
C2—C1—C6—C5	−0.59 (18)	Zn1—N3—C13—C8	37.35 (12)
C4—C5—C6—N2	−178.24 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···Cl1ⁱ	0.82	2.56	3.3503 (9)	164
N3—H1N3···Cl1ⁱⁱ	0.89	2.49	3.3753 (9)	174
N3—H2N3···Cl2ⁱⁱⁱ	0.94	2.44	3.3015 (12)	153

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

Experimental details

Crystal data
Chemical formula	[ZnCl₂(C₁₃H₁₁N₃)]
M_r	345.54
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	100
a, b, c (Å)	22.0252 (7), 10.0651 (3), 15.3676 (6)
β (°)	125.244 (2)
V (Å³)	2782.32 (18)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	2.14
Crystal size (mm)	0.48 × 0.31 × 0.31

Data collection
Diffractometer	Bruker APEX DUO CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.428, 0.560
No. of measured, independent and observed [I > 2σ(I)] reflections	50659, 7344, 5887
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.859

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.027, 0.081, 1.02
No. of reflections	7344
No. of parameters	172
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.54, −0.55

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···Cl1ⁱ	0.82	2.56	3.3503 (9)	164
N3—H1N3···Cl1ⁱⁱ	0.89	2.49	3.3753 (9)	174
N3—H2N3···Cl2ⁱⁱⁱ	0.94	2.44	3.3015 (12)	153

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

Footnotes

‡Thomson Reuters ResearcherID: A-5085-2009.

§Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

The authors thank the Malaysian Government and Universiti Sains Malaysia for the RU research grant (1001/PKIMIA/815067). NEE thanks Universiti Sains Malaysia for a post-doctoral fellowship and the International University of Africa (Sudan) for providing study leave. The authors also thank Universiti Sains Malaysia for the Research University grant No. 1001/PFIZIK/811160.

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