Di-μ-thio­cyanato-κ2N:S;κ2S:N-bis­[bis­(2-methyl-1H-benzimidazole-κN3)(thio­cyanato-κN)cadmium(II)]

Shaker, S.A.; Khaledi, H.; Mohd Ali, H.

doi:10.1107/S1600536810042443

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 11| November 2010| Page m1464

https://doi.org/10.1107/S1600536810042443

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Di-μ-thiocyanato-κ²N:S;κ²S:N-bis[bis(2-methyl-1H-benzimidazole-κN³)(thiocyanato-κN)cadmium(II)]

Shayma A. Shaker,^a Hamid Khaledi ^a ^* and Hapipah Mohd Ali ^a

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: khaledi@siswa.um.edu.my

(Received 12 October 2010; accepted 19 October 2010; online 23 October 2010)

The title compound, [Cd₂(NCS)₄(C₈H₈N₂)₄], is a centrosymmetric dinuclear cadmium(II) complex in which each two metal ions are linked by a pair of thiocyanate N:S-bridges. Two 2-methylbenzimidazole N-atom donors and one terminal thiocyanate N atom complete a highly distorted square-pyramidal geometry around the Cd atom. In the crystal structure, two N—H⋯S hydrogen-bonding interactions occur, resulting in a three-dimensional polymeric structure. The apical 2-methylbenzimidazole ring and its symmetry-related counterpart are arranged in an antiparallel manner with a centroid–centroid separation of 3.6050 (14) Å, indicative of a π–π interaction.

Related literature

For cadmium complexes having a [Cd₂(μ₂-NCS)₂(NCS)₂] unit, see: Gou et al. (2008 ); Govor et al. (2008 ); Shi et al. (2004 ).

Experimental

Crystal data

[Cd₂(NCS)₄(C₈H₈N₂)₄]
M_r = 985.78
Monoclinic, C 2/c
a = 18.1519 (11) Å
b = 10.2098 (6) Å
c = 21.7385 (13) Å
β = 97.864 (1)°
V = 3990.8 (4) Å³
Z = 4
Mo Kα radiation
μ = 1.32 mm⁻¹
T = 100 K
0.38 × 0.20 × 0.13 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.634, T_max = 0.847
9361 measured reflections
3593 independent reflections
3213 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.021
wR(F²) = 0.047
S = 1.03
3593 reflections
253 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2N⋯S1ⁱ	0.86 (2)	2.45 (2)	3.273 (2)	163 (2)
N4—H4N⋯S1ⁱⁱ	0.84 (2)	2.48 (2)	3.281 (2)	159 (2)
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[x-{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ .

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810042443/pk2278sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810042443/pk2278Isup2.hkl

checkCIF report

Comment top

The title compound is a mixed-ligand cadmium(II) complex with thiocyanate and 2-methylbenzimidazole. The thiocyanate ions act as either bridging or terminal ligands. The pairs of the former, link each two metal ions into a centrosymmetric dinuclear complex. The resulting eight-membered Cd₂(µ₂-NCS)₂ring is almost planar (r.m.s = 0.015), unlike the chair conformation observed in most of the similar structures (Gou et al. 2008; Govor et al. 2008; Shi et al. 2004). The terminal thiocyanate ligand forms two types of hydrogen bond with the amine hydrogen atoms (Fig. 2), leading to an infinite three-dimensional network. Two 2-methylbenzimidazole ligands, one in the apical position and the other one equatorially positioned, complete the penta-coordinate cadmium(II) complex in a highly distorted square pyramidal geometry (τ = 0.26). The apical 2-methylbenzimidazole ring and its symmetry related counterpart at (-x+1, -y, -z+1) are arranged in an antiparallel manner with separation of 3.6050 (14) Å, indicative of a π-π interaction.

Related literature top

For cadmium(II) complexes having a [Cd₂(µ₂-NCS)₂(NCS)₂] unit, see: Gou et al. (2008); Govor et al. (2008); Shi et al. (2004).

Experimental top

An ethanolic solution (15 ml) of 2-methylbenzimidazole (1.32 g, 10 mmol) was added to an aqueous solution (20 ml) of CdCl₂. H₂O (0.5 g, 2.5 mmol) followed by addition of an aqueous solution (15 ml) of KSCN (0.49 g, 5 mmol). The mixture was heated in a water bath for 30 min with constant stirring. The resulting precipitate was filtered off and recrystallized from ethanol to give the colorless crystals of the title cadmium(II) complex.

Structure description top

For cadmium(II) complexes having a [Cd₂(µ₂-NCS)₂(NCS)₂] unit, see: Gou et al. (2008); Govor et al. (2008); Shi et al. (2004).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of the title compound showing displacement ellipsoids at the 50% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius. The unlabelled atoms are generated by the symmetry operation (–x + 1, –y + 1, –z + 1).
	Fig. 2. A view of the hydrogen bonding interactions (dashed lines). C-bound hydrogen atoms have been omitted for clarity. Symmetry codes: (i) -x + 1, -y + 1, -z + 1; (ii) x + 1/2, y + 1/2, z; (iii) -x + 3/2, -y + 3/2, -z + 1/2; (iv) -x+3/2, y - 1/2, - z+3/2.

Di-µ-thiocyanato-κ²N:S;κ²S:N- bis[bis(2-methyl-1H-benzimidazole-κN³)(thiocyanato- κN)cadmium(II)] top

Crystal data top

[Cd₂(NCS)₄(C₈H₈N₂)₄]	F(000) = 1968
M_r = 985.78	D_x = 1.641 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4666 reflections
a = 18.1519 (11) Å	θ = 2.3–30.1°
b = 10.2098 (6) Å	µ = 1.32 mm⁻¹
c = 21.7385 (13) Å	T = 100 K
β = 97.864 (1)°	Block, colorless
V = 3990.8 (4) Å³	0.38 × 0.20 × 0.13 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	3593 independent reflections
Radiation source: fine-focus sealed tube	3213 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
φ and ω scans	θ_max = 25.2°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −21→21
T_min = 0.634, T_max = 0.847	k = −12→8
9361 measured reflections	l = −26→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)] = 0.021	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.047	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0169P)² + 6.0676P] where P = (F_o² + 2F_c²)/3
3593 reflections	(Δ/σ)_max = 0.003
253 parameters	Δρ_max = 0.35 e Å⁻³
3 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

[Cd₂(NCS)₄(C₈H₈N₂)₄]	V = 3990.8 (4) Å³
M_r = 985.78	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 18.1519 (11) Å	µ = 1.32 mm⁻¹
b = 10.2098 (6) Å	T = 100 K
c = 21.7385 (13) Å	0.38 × 0.20 × 0.13 mm
β = 97.864 (1)°

Data collection top

Bruker APEXII CCD diffractometer	3593 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3213 reflections with I > 2σ(I)
T_min = 0.634, T_max = 0.847	R_int = 0.022
9361 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.021	3 restraints
wR(F²) = 0.047	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.35 e Å⁻³
3593 reflections	Δρ_min = −0.31 e Å⁻³
253 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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
Cd1	0.611050 (9)	0.354819 (16)	0.590885 (7)	0.01561 (6)
S1	0.88100 (3)	0.33657 (6)	0.67126 (3)	0.02608 (15)
S2	0.63546 (3)	0.42113 (7)	0.47897 (3)	0.02741 (16)
N1	0.62322 (10)	0.41831 (19)	0.69141 (9)	0.0181 (4)
N2	0.63781 (11)	0.5391 (2)	0.77688 (9)	0.0211 (5)
H2N	0.6364 (14)	0.609 (2)	0.7982 (11)	0.025*
N3	0.57608 (10)	0.14637 (19)	0.58946 (8)	0.0166 (4)
N4	0.50684 (11)	−0.0294 (2)	0.59628 (9)	0.0193 (4)
H4N	0.4715 (12)	−0.075 (2)	0.6062 (11)	0.023*
N5	0.73824 (11)	0.3290 (2)	0.60377 (10)	0.0258 (5)
N6	0.49556 (11)	0.4528 (2)	0.57293 (9)	0.0227 (5)
C1	0.57531 (15)	0.6482 (2)	0.68162 (12)	0.0279 (6)
H1A	0.5852	0.6462	0.6384	0.042*
H1B	0.5953	0.7293	0.7014	0.042*
H1C	0.5215	0.6444	0.6826	0.042*
C2	0.61150 (12)	0.5342 (2)	0.71553 (11)	0.0195 (5)
C3	0.67023 (13)	0.4198 (2)	0.79411 (11)	0.0199 (5)
C4	0.70777 (13)	0.3741 (3)	0.85017 (11)	0.0256 (6)
H4	0.7157	0.4277	0.8862	0.031*
C5	0.73278 (13)	0.2465 (3)	0.85032 (11)	0.0267 (6)
H5	0.7590	0.2115	0.8875	0.032*
C6	0.72085 (13)	0.1674 (3)	0.79777 (11)	0.0244 (6)
H6	0.7376	0.0791	0.8004	0.029*
C7	0.68519 (13)	0.2141 (2)	0.74170 (11)	0.0207 (5)
H7	0.6782	0.1606	0.7056	0.025*
C8	0.66004 (12)	0.3433 (2)	0.74051 (10)	0.0180 (5)
C9	0.47424 (14)	0.1670 (2)	0.65538 (11)	0.0235 (6)
H9A	0.5070	0.1980	0.6921	0.035*
H9B	0.4369	0.1074	0.6683	0.035*
H9C	0.4493	0.2419	0.6333	0.035*
C10	0.51909 (12)	0.0964 (2)	0.61350 (10)	0.0180 (5)
C11	0.55900 (12)	−0.0656 (2)	0.55862 (10)	0.0179 (5)
C12	0.57193 (13)	−0.1818 (2)	0.52880 (11)	0.0215 (5)
H12	0.5417	−0.2570	0.5316	0.026*
C13	0.63096 (14)	−0.1828 (2)	0.49486 (11)	0.0224 (5)
H13	0.6421	−0.2610	0.4743	0.027*
C14	0.67477 (13)	−0.0712 (2)	0.49010 (11)	0.0221 (5)
H14	0.7146	−0.0752	0.4660	0.027*
C15	0.66144 (13)	0.0441 (2)	0.51961 (10)	0.0191 (5)
H15	0.6914	0.1194	0.5164	0.023*
C16	0.60252 (12)	0.0460 (2)	0.55436 (10)	0.0162 (5)
C17	0.79736 (13)	0.3327 (2)	0.63127 (11)	0.0190 (5)
C18	0.55777 (13)	0.4945 (2)	0.44892 (10)	0.0181 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cd1	0.01419 (9)	0.01624 (10)	0.01592 (9)	−0.00017 (7)	0.00037 (6)	−0.00061 (7)
S1	0.0177 (3)	0.0296 (4)	0.0292 (3)	−0.0058 (3)	−0.0026 (3)	0.0120 (3)
S2	0.0179 (3)	0.0383 (4)	0.0273 (3)	0.0099 (3)	0.0080 (3)	0.0139 (3)
N1	0.0166 (10)	0.0187 (11)	0.0187 (10)	0.0004 (8)	0.0009 (8)	−0.0010 (9)
N2	0.0222 (11)	0.0219 (12)	0.0193 (11)	0.0006 (9)	0.0026 (9)	−0.0070 (9)
N3	0.0148 (9)	0.0179 (10)	0.0169 (9)	−0.0008 (8)	0.0016 (8)	0.0001 (8)
N4	0.0176 (10)	0.0214 (11)	0.0190 (10)	−0.0059 (8)	0.0024 (8)	0.0023 (9)
N5	0.0183 (11)	0.0351 (13)	0.0245 (11)	0.0003 (9)	0.0043 (9)	0.0033 (10)
N6	0.0210 (11)	0.0283 (12)	0.0188 (10)	0.0040 (9)	0.0031 (9)	−0.0008 (9)
C1	0.0305 (14)	0.0229 (14)	0.0288 (13)	0.0028 (11)	−0.0010 (12)	−0.0035 (12)
C2	0.0150 (11)	0.0213 (13)	0.0223 (12)	−0.0009 (10)	0.0027 (10)	−0.0012 (11)
C3	0.0160 (12)	0.0262 (14)	0.0181 (12)	−0.0029 (10)	0.0043 (10)	−0.0003 (11)
C4	0.0209 (13)	0.0399 (17)	0.0162 (12)	−0.0057 (11)	0.0033 (10)	−0.0021 (11)
C5	0.0186 (13)	0.0414 (17)	0.0202 (13)	0.0015 (11)	0.0023 (10)	0.0108 (12)
C6	0.0185 (12)	0.0260 (14)	0.0298 (14)	0.0029 (10)	0.0071 (11)	0.0095 (11)
C7	0.0177 (12)	0.0222 (14)	0.0222 (12)	0.0005 (10)	0.0027 (10)	0.0000 (11)
C8	0.0138 (11)	0.0215 (13)	0.0185 (12)	−0.0012 (10)	0.0018 (9)	0.0018 (10)
C9	0.0232 (13)	0.0284 (15)	0.0197 (12)	−0.0038 (11)	0.0061 (10)	−0.0028 (11)
C10	0.0164 (12)	0.0220 (13)	0.0148 (11)	−0.0014 (10)	−0.0002 (10)	0.0035 (10)
C11	0.0178 (12)	0.0211 (13)	0.0139 (11)	−0.0015 (10)	−0.0016 (9)	0.0039 (10)
C12	0.0248 (13)	0.0182 (13)	0.0198 (12)	−0.0046 (10)	−0.0025 (10)	0.0013 (10)
C13	0.0256 (13)	0.0197 (13)	0.0206 (12)	0.0024 (10)	−0.0010 (11)	−0.0029 (10)
C14	0.0194 (12)	0.0262 (14)	0.0208 (12)	0.0011 (10)	0.0032 (10)	−0.0010 (11)
C15	0.0174 (12)	0.0184 (13)	0.0210 (12)	−0.0023 (10)	0.0002 (10)	0.0004 (10)
C16	0.0156 (11)	0.0176 (12)	0.0141 (11)	0.0004 (9)	−0.0023 (9)	0.0016 (10)
C17	0.0201 (12)	0.0184 (13)	0.0193 (12)	−0.0006 (10)	0.0061 (10)	0.0050 (10)
C18	0.0177 (12)	0.0207 (13)	0.0164 (12)	−0.0015 (10)	0.0048 (10)	0.0004 (10)

Geometric parameters (Å, º) top

Cd1—N3	2.2199 (19)	C3—C8	1.394 (3)
Cd1—N1	2.2611 (19)	C4—C5	1.379 (4)
Cd1—N5	2.302 (2)	C4—H4	0.9500
Cd1—N6	2.307 (2)	C5—C6	1.392 (4)
Cd1—S2	2.6207 (7)	C5—H5	0.9500
S1—C17	1.644 (2)	C6—C7	1.385 (3)
S2—C18	1.651 (2)	C6—H6	0.9500
N1—C2	1.323 (3)	C7—C8	1.394 (3)
N1—C8	1.406 (3)	C7—H7	0.9500
N2—C2	1.355 (3)	C9—C10	1.488 (3)
N2—C3	1.382 (3)	C9—H9A	0.9800
N2—H2N	0.856 (17)	C9—H9B	0.9800
N3—C10	1.323 (3)	C9—H9C	0.9800
N3—C16	1.401 (3)	C11—C12	1.388 (3)
N4—C10	1.347 (3)	C11—C16	1.396 (3)
N4—C11	1.384 (3)	C12—C13	1.382 (3)
N4—H4N	0.844 (16)	C12—H12	0.9500
N5—C17	1.155 (3)	C13—C14	1.401 (3)
N6—C18ⁱ	1.152 (3)	C13—H13	0.9500
C1—C2	1.482 (3)	C14—C15	1.378 (3)
C1—H1A	0.9800	C14—H14	0.9500
C1—H1B	0.9800	C15—C16	1.391 (3)
C1—H1C	0.9800	C15—H15	0.9500
C3—C4	1.393 (3)	C18—N6ⁱ	1.152 (3)

N3—Cd1—N1	106.16 (7)	C4—C5—H5	118.9
N3—Cd1—N5	99.90 (7)	C6—C5—H5	118.9
N1—Cd1—N5	87.22 (7)	C7—C6—C5	121.6 (2)
N3—Cd1—N6	99.32 (7)	C7—C6—H6	119.2
N1—Cd1—N6	90.32 (7)	C5—C6—H6	119.2
N5—Cd1—N6	160.55 (7)	C6—C7—C8	117.1 (2)
N3—Cd1—S2	108.61 (5)	C6—C7—H7	121.5
N1—Cd1—S2	144.74 (5)	C8—C7—H7	121.5
N5—Cd1—S2	81.28 (5)	C3—C8—C7	120.6 (2)
N6—Cd1—S2	89.77 (5)	C3—C8—N1	108.9 (2)
C18—S2—Cd1	103.94 (8)	C7—C8—N1	130.5 (2)
C2—N1—C8	105.77 (19)	C10—C9—H9A	109.5
C2—N1—Cd1	129.77 (16)	C10—C9—H9B	109.5
C8—N1—Cd1	123.42 (15)	H9A—C9—H9B	109.5
C2—N2—C3	108.3 (2)	C10—C9—H9C	109.5
C2—N2—H2N	122.1 (18)	H9A—C9—H9C	109.5
C3—N2—H2N	129.4 (18)	H9B—C9—H9C	109.5
C10—N3—C16	106.11 (19)	N3—C10—N4	111.5 (2)
C10—N3—Cd1	126.99 (16)	N3—C10—C9	125.3 (2)
C16—N3—Cd1	126.17 (15)	N4—C10—C9	123.2 (2)
C10—N4—C11	108.57 (19)	N4—C11—C12	132.7 (2)
C10—N4—H4N	123.9 (18)	N4—C11—C16	105.1 (2)
C11—N4—H4N	127.4 (18)	C12—C11—C16	122.2 (2)
C17—N5—Cd1	154.70 (19)	C13—C12—C11	116.7 (2)
C18ⁱ—N6—Cd1	164.86 (18)	C13—C12—H12	121.7
C2—C1—H1A	109.5	C11—C12—H12	121.7
C2—C1—H1B	109.5	C12—C13—C14	121.5 (2)
H1A—C1—H1B	109.5	C12—C13—H13	119.2
C2—C1—H1C	109.5	C14—C13—H13	119.2
H1A—C1—H1C	109.5	C15—C14—C13	121.5 (2)
H1B—C1—H1C	109.5	C15—C14—H14	119.2
N1—C2—N2	111.7 (2)	C13—C14—H14	119.2
N1—C2—C1	126.1 (2)	C14—C15—C16	117.5 (2)
N2—C2—C1	122.2 (2)	C14—C15—H15	121.2
N2—C3—C4	132.2 (2)	C16—C15—H15	121.2
N2—C3—C8	105.3 (2)	C15—C16—C11	120.5 (2)
C4—C3—C8	122.4 (2)	C15—C16—N3	130.7 (2)
C5—C4—C3	116.1 (2)	C11—C16—N3	108.8 (2)
C5—C4—H4	121.9	N5—C17—S1	179.1 (2)
C3—C4—H4	121.9	N6ⁱ—C18—S2	178.5 (2)
C4—C5—C6	122.2 (2)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···S1ⁱⁱ	0.86 (2)	2.45 (2)	3.273 (2)	163 (2)
N4—H4N···S1ⁱⁱⁱ	0.84 (2)	2.48 (2)	3.281 (2)	159 (2)

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

Experimental details

Crystal data
Chemical formula	[Cd₂(NCS)₄(C₈H₈N₂)₄]
M_r	985.78
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	100
a, b, c (Å)	18.1519 (11), 10.2098 (6), 21.7385 (13)
β (°)	97.864 (1)
V (Å³)	3990.8 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.32
Crystal size (mm)	0.38 × 0.20 × 0.13

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.634, 0.847
No. of measured, independent and observed [I > 2σ(I)] reflections	9361, 3593, 3213
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.599

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.021, 0.047, 1.03
No. of reflections	3593
No. of parameters	253
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.31

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···S1ⁱ	0.856 (17)	2.445 (18)	3.273 (2)	163 (2)
N4—H4N···S1ⁱⁱ	0.844 (16)	2.481 (18)	3.281 (2)	159 (2)

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

Acknowledgements

The authors thank University of Malaya for funding this study (UMRG grant RG024/09BIO).

References

Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Gou, L., Wu, Q. R., Hu, H. M., Qin, T., Xue, G. L., Yang, M. L. & Tang, Z. X. (2008). Polyhedron, 27, 1517–1526. Web of Science CSD CrossRef CAS Google Scholar
Govor, E. V., Lysenko, A. B., Domasevitch, K. V., Rusanov, E. B. & Chernega, A. N. (2008). Acta Cryst. C64, m117–m120. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Shi, Q., Xu, L. J., Ji, J. X., Li, Y. M., Wang, R. H., Zhou, Z. Y., Cao, R., Hong, M. C. & Chan, A. S. C. (2004). Inorg. Chem. Commun. 7, 1254–1257. Web of Science CSD CrossRef CAS Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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