Aquachloridobis[2-(1,3-thia­zol-4-yl-κN)-1H-benzimidazole-κN3]nickel(II) nitrate

Liang, P.; Wu, W.; Tian, W.-M.; Yin, X.-H.

doi:10.1107/S1600536812029728

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 8| August 2012| Page m1029

https://doi.org/10.1107/S1600536812029728

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Aquachloridobis[2-(1,3-thiazol-4-yl-κN)-1H-benzimidazole-κN³]nickel(II) nitrate

Peng Liang,^a Wei Wu,^a Wei-Man Tian ^a and Xian-Hong Yin ^a ^*

^aDepartment of Chemistry and Chemical Engineering, Guangxi University for Nationalities, Nanning 530006, People's Republic of China
^*Correspondence e-mail: 6628yxh@163.com

(Received 19 May 2012; accepted 29 June 2012; online 4 July 2012)

In the title compound, [NiCl(C₁₀H₇N₃S)₂(H₂O)]NO₃, the Ni^II ion is coordinated by four N atoms from two chelating 2-(1,3-thiazol-4-yl)-1H-benzimidazole ligands, one Cl atom and one water molecule in a distorted octahedral geometry. In the crystal, O—H⋯O, N—H⋯O and N—H⋯Cl hydrogen bonds link the complex cations and nitrate anions into a three-dimensional network. π–π interactions between the thiazole and imidazole rings and between the thiazole and benzene rings are observed [centroid–centroid distances = 3.592 (3) and 3.735 (3) Å].

Related literature

For background to the synthesis and properties of benzimidazole derivatives, see: Agh-Atabay et al. (2003 ); Devereux et al. (2004 ); Inoue et al. (2002 ). For a related structure, see: Mothilal et al. (2004 ).

Experimental

Crystal data

[NiCl(C₁₀H₇N₃S)₂(H₂O)]NO₃
M_r = 576.68
Monoclinic, P 2₁ /c
a = 16.091 (5) Å
b = 11.189 (3) Å
c = 13.931 (3) Å
β = 113.275 (3)°
V = 2304.1 (11) Å³
Z = 4
Mo Kα radiation
μ = 1.18 mm⁻¹
T = 296 K
0.26 × 0.25 × 0.24 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.748, T_max = 0.764
11654 measured reflections
4050 independent reflections
3129 reflections with I > 2σ(I)
R_int = 0.072

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.174
S = 1.07
4050 reflections
316 parameters
H-atom parameters constrained
Δρ_max = 0.80 e Å⁻³
Δρ_min = −0.53 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯O3ⁱ	0.84	2.00	2.751 (5)	149
O1—H1B⋯O2ⁱⁱ	0.79	2.53	3.293 (6)	160
O1—H1B⋯O4ⁱⁱ	0.79	2.38	3.025 (5)	139
N4—H4⋯O3ⁱⁱⁱ	0.86	2.35	2.962 (5)	129
N4—H4⋯O4ⁱⁱⁱ	0.86	2.14	2.996 (5)	173
N7—H7⋯Cl1^iv	0.86	2.35	3.159 (4)	157
Symmetry codes: (i) x-1, y, z; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[x-1, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (iv) -x+1, -y+1, -z+1.

Data collection: SMART (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: DIAMOND (Brandenburg, 1999 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536812029728/hy2553sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812029728/hy2553Isup2.hkl

checkCIF report

Comment top

Thiabendazole (TBZ) aroused considerable interest in biology and medicine due to its antiproliferative activities. It is an antimicrobial drug belonging to the benzimidazole derivatives and exhibits wide applications in human and veterinary medicine (Agh-Atabay et al., 2003; Devereux et al., 2004; Inoue et al., 2002). As part of our studies of the synthesis and characterization of these compounds, we report here the synthesis and crystal structure of the title compound (Fig. 1).

In the crystal, intermolecular O—H···O, N—H···O and N—H···Cl hydrogen bonds link the complex cations and nitrate anions into a three-dimensional network (Table 1, Fig. 2) (Mothilal et al., 2004). π–π interactions between the thiazole and imidazole rings and between the thiazole and benzene rings are observed [centroid–centroid distances = 3.592 (3) and 3.735 (3) Å]. In the complex cation, the two ligand planes are nearly perpendicular to each other, with a dihedral angle of 89.14 (7)°.

Related literature top

For background to the synthesis and properties of benzimidazole derivatives, see: Agh-Atabay et al. (2003); Devereux et al. (2004); Inoue et al. (2002). For a related structure, see: Mothilal et al. (2004).

Experimental top

A solution of TBZ (0.201 g, 1 mmol) in 3 ml DMF was added dropwise with stirring at room temperature to a solution of Ni(NO₃)₂.6H₂O (0.290 g, 1 mmol) and NiCl₂.6H₂O (0.237 g, 1 mmol) in a mixture of 10 ml water and 5 ml ethanol. Then an aqueous solution of sodium hydroxide was added dropwise with stirring to adjust the pH value of the solution being 6. The resulting mixture was sealed in a 23 ml Teflon-lined stainless reactor, kept under autogenous pressure at 403 K for 72 h, and then slowly cooled to room temperature at a rate of 5 K per hour. Dark-green block crystals suitable for X-ray diffraction were isolated, washed with ethanol and dried in air (yield: 65% based on Ni).

Structure description top

For background to the synthesis and properties of benzimidazole derivatives, see: Agh-Atabay et al. (2003); Devereux et al. (2004); Inoue et al. (2002). For a related structure, see: Mothilal et al. (2004).

Computing details top

Data collection: SMART (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: DIAMOND (Brandenburg, 1999); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The Molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level. H atoms have been omitted for clarity.
	Fig. 2. Crystal packing of the title compound. Dashed lines denote hydrogen bonds.

Aquachloridobis[2-(1,3-thiazol-4-yl-κN)- 1H-benzimidazole-κN³]nickel(II) nitrate top

Crystal data top

[NiCl(C₁₀H₇N₃S)₂(H₂O)]NO₃	F(000) = 1176
M_r = 576.68	D_x = 1.662 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2584 reflections
a = 16.091 (5) Å	θ = 2.3–26.6°
b = 11.189 (3) Å	µ = 1.18 mm⁻¹
c = 13.931 (3) Å	T = 296 K
β = 113.275 (3)°	Block, green
V = 2304.1 (11) Å³	0.26 × 0.25 × 0.24 mm
Z = 4

Data collection top

Bruker SMART APEX CCD diffractometer	4050 independent reflections
Radiation source: fine-focus sealed tube	3129 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.072
φ and ω scans	θ_max = 25.0°, θ_min = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −18→19
T_min = 0.748, T_max = 0.764	k = −13→13
11654 measured reflections	l = −14→16

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.174	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.083P)² + 1.4424P] where P = (F_o² + 2F_c²)/3
4050 reflections	(Δ/σ)_max = 0.045
316 parameters	Δρ_max = 0.80 e Å⁻³
0 restraints	Δρ_min = −0.53 e Å⁻³

Crystal data top

[NiCl(C₁₀H₇N₃S)₂(H₂O)]NO₃	V = 2304.1 (11) Å³
M_r = 576.68	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 16.091 (5) Å	µ = 1.18 mm⁻¹
b = 11.189 (3) Å	T = 296 K
c = 13.931 (3) Å	0.26 × 0.25 × 0.24 mm
β = 113.275 (3)°

Data collection top

Bruker SMART APEX CCD diffractometer	4050 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3129 reflections with I > 2σ(I)
T_min = 0.748, T_max = 0.764	R_int = 0.072
11654 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	0 restraints
wR(F²) = 0.174	H-atom parameters constrained
S = 1.07	Δρ_max = 0.80 e Å⁻³
4050 reflections	Δρ_min = −0.53 e Å⁻³
316 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
Ni1	0.26114 (3)	0.47368 (5)	0.32612 (4)	0.0352 (2)
Cl1	0.31740 (8)	0.27662 (10)	0.40665 (10)	0.0490 (4)
S1	0.36620 (9)	0.71229 (11)	0.62788 (10)	0.0507 (4)
S2	0.13043 (9)	0.27528 (12)	0.00588 (11)	0.0552 (4)
O1	0.13949 (19)	0.4517 (3)	0.3478 (3)	0.0412 (7)
O3	1.0666 (2)	0.6635 (3)	0.3784 (3)	0.0606 (10)
O4	1.0018 (2)	0.8339 (3)	0.3421 (3)	0.0693 (11)
O2	0.9808 (3)	0.7045 (5)	0.2204 (3)	0.0964 (18)
N3	0.2001 (2)	0.3971 (3)	0.1739 (3)	0.0344 (8)
N5	0.3884 (2)	0.5240 (3)	0.3241 (3)	0.0313 (8)
N6	0.3205 (2)	0.5777 (3)	0.4687 (3)	0.0324 (8)
N2	0.2024 (2)	0.6272 (3)	0.2292 (3)	0.0343 (8)
N7	0.5158 (2)	0.6289 (3)	0.3975 (3)	0.0370 (9)
H7	0.5562	0.6742	0.4414	0.044*
N4	0.1133 (2)	0.6929 (3)	0.0713 (3)	0.0430 (9)
H4	0.0801	0.6916	0.0054	0.052*
N1	1.0157 (2)	0.7334 (4)	0.3117 (3)	0.0447 (10)
C8	0.4375 (3)	0.5129 (4)	0.2623 (3)	0.0343 (10)
C15	0.1532 (3)	0.4763 (4)	0.0953 (4)	0.0368 (10)
C20	0.5192 (3)	0.5792 (4)	0.3096 (4)	0.0371 (10)
C7	0.1553 (3)	0.5995 (4)	0.1300 (3)	0.0339 (9)
C19	0.4372 (2)	0.5941 (3)	0.4029 (3)	0.0321 (9)
C17	0.4038 (2)	0.6273 (3)	0.4827 (3)	0.0327 (9)
C6	0.1899 (3)	0.7514 (4)	0.2356 (4)	0.0388 (10)
C13	0.1927 (3)	0.2884 (4)	0.1364 (4)	0.0419 (11)
H13	0.2196	0.2229	0.1783	0.050*
C5	0.1327 (3)	0.7920 (4)	0.1353 (4)	0.0441 (11)
C18	0.4377 (3)	0.7027 (4)	0.5649 (4)	0.0421 (11)
H18	0.4923	0.7435	0.5842	0.051*
C11	0.5629 (4)	0.5228 (5)	0.1731 (5)	0.0571 (14)
H11	0.6040	0.5248	0.1412	0.069*
C1	0.2222 (3)	0.8290 (4)	0.3202 (4)	0.0495 (12)
H1	0.2602	0.8024	0.3862	0.059*
C12	0.5820 (3)	0.5849 (5)	0.2636 (5)	0.0540 (14)
H12	0.6349	0.6294	0.2935	0.065*
C14	0.1106 (3)	0.4261 (5)	−0.0009 (4)	0.0467 (12)
H14	0.0759	0.4676	−0.0613	0.056*
C10	0.4830 (4)	0.4559 (5)	0.1265 (4)	0.0507 (12)
H10	0.4723	0.4144	0.0649	0.061*
C9	0.4209 (3)	0.4511 (4)	0.1705 (4)	0.0443 (11)
H9	0.3681	0.4069	0.1392	0.053*
C16	0.2942 (3)	0.6140 (4)	0.5385 (4)	0.0412 (11)
H16	0.2400	0.5892	0.5412	0.049*
C4	0.1057 (4)	0.9106 (5)	0.1180 (5)	0.0562 (14)
H4A	0.0679	0.9375	0.0520	0.067*
C2	0.1958 (4)	0.9471 (4)	0.3023 (5)	0.0612 (15)
H2	0.2169	1.0019	0.3569	0.073*
C3	0.1367 (4)	0.9856 (4)	0.2012 (6)	0.0661 (18)
H3	0.1186	1.0652	0.1916	0.079*
H1A	0.1016	0.5069	0.3358	0.079*
H1B	0.1000	0.4040	0.3241	0.079*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0293 (3)	0.0361 (3)	0.0344 (4)	−0.0022 (2)	0.0065 (3)	−0.0048 (2)
Cl1	0.0429 (6)	0.0411 (6)	0.0506 (8)	0.0038 (5)	0.0053 (5)	0.0024 (5)
S1	0.0636 (8)	0.0451 (6)	0.0402 (8)	−0.0015 (5)	0.0170 (6)	−0.0142 (5)
S2	0.0516 (7)	0.0592 (8)	0.0476 (8)	−0.0047 (6)	0.0119 (6)	−0.0238 (6)
O1	0.0344 (15)	0.0363 (15)	0.051 (2)	−0.0037 (12)	0.0148 (14)	−0.0003 (14)
O3	0.072 (2)	0.054 (2)	0.046 (2)	0.0172 (18)	0.0134 (19)	0.0004 (17)
O4	0.059 (2)	0.057 (2)	0.093 (3)	0.0218 (18)	0.032 (2)	0.011 (2)
O2	0.090 (3)	0.159 (5)	0.025 (2)	−0.052 (3)	0.006 (2)	−0.010 (2)
N3	0.0294 (16)	0.0339 (17)	0.034 (2)	−0.0017 (14)	0.0065 (15)	−0.0072 (15)
N5	0.0255 (16)	0.0344 (17)	0.029 (2)	−0.0029 (13)	0.0058 (15)	−0.0020 (15)
N6	0.0306 (17)	0.0380 (18)	0.025 (2)	0.0000 (14)	0.0077 (15)	−0.0059 (15)
N2	0.0346 (17)	0.0303 (17)	0.035 (2)	−0.0006 (14)	0.0104 (16)	−0.0017 (15)
N7	0.0291 (16)	0.0394 (18)	0.036 (2)	−0.0067 (14)	0.0055 (16)	0.0033 (16)
N4	0.042 (2)	0.045 (2)	0.036 (2)	0.0034 (17)	0.0087 (17)	0.0068 (18)
N1	0.0357 (19)	0.061 (3)	0.038 (2)	−0.0123 (18)	0.0146 (18)	0.001 (2)
C8	0.032 (2)	0.035 (2)	0.033 (2)	0.0016 (17)	0.0102 (19)	0.0018 (18)
C15	0.032 (2)	0.045 (2)	0.032 (3)	−0.0053 (17)	0.0113 (19)	−0.0058 (19)
C20	0.034 (2)	0.034 (2)	0.044 (3)	0.0039 (17)	0.0153 (19)	0.010 (2)
C7	0.0296 (19)	0.040 (2)	0.033 (2)	0.0007 (17)	0.0126 (18)	0.0016 (18)
C19	0.0265 (18)	0.033 (2)	0.033 (2)	0.0024 (16)	0.0076 (18)	0.0031 (18)
C17	0.0296 (19)	0.0275 (18)	0.032 (2)	−0.0016 (16)	0.0032 (17)	0.0002 (17)
C6	0.033 (2)	0.030 (2)	0.054 (3)	−0.0005 (17)	0.017 (2)	0.004 (2)
C13	0.031 (2)	0.044 (2)	0.046 (3)	−0.0004 (18)	0.010 (2)	−0.009 (2)
C5	0.039 (2)	0.045 (3)	0.054 (3)	0.0063 (19)	0.024 (2)	0.018 (2)
C18	0.042 (2)	0.037 (2)	0.040 (3)	−0.0067 (18)	0.007 (2)	−0.0074 (19)
C11	0.069 (3)	0.057 (3)	0.062 (4)	0.013 (3)	0.043 (3)	0.017 (3)
C1	0.048 (3)	0.035 (2)	0.065 (3)	0.001 (2)	0.021 (2)	−0.003 (2)
C12	0.040 (2)	0.053 (3)	0.071 (4)	0.003 (2)	0.024 (3)	0.023 (3)
C14	0.045 (2)	0.057 (3)	0.033 (3)	−0.002 (2)	0.010 (2)	0.001 (2)
C10	0.064 (3)	0.055 (3)	0.040 (3)	0.004 (2)	0.028 (3)	0.006 (2)
C9	0.046 (3)	0.043 (2)	0.043 (3)	0.001 (2)	0.018 (2)	−0.001 (2)
C16	0.036 (2)	0.046 (2)	0.038 (3)	−0.0030 (19)	0.012 (2)	−0.004 (2)
C4	0.060 (3)	0.045 (3)	0.071 (4)	0.016 (2)	0.035 (3)	0.022 (3)
C2	0.069 (3)	0.038 (2)	0.092 (5)	−0.002 (2)	0.048 (3)	−0.005 (3)
C3	0.067 (3)	0.034 (2)	0.116 (6)	0.011 (2)	0.057 (4)	0.013 (3)

Geometric parameters (Å, º) top

Ni1—O1	2.109 (3)	C8—C9	1.383 (6)
Ni1—N3	2.133 (3)	C8—C20	1.424 (6)
Ni1—N5	2.134 (3)	C15—C14	1.361 (6)
Ni1—N2	2.159 (3)	C15—C7	1.456 (6)
Ni1—N6	2.171 (3)	C20—C12	1.396 (7)
Ni1—Cl1	2.4772 (13)	C19—C17	1.461 (6)
S1—C18	1.704 (5)	C17—C18	1.351 (6)
S1—C16	1.721 (4)	C6—C1	1.389 (7)
S2—C13	1.700 (5)	C6—C5	1.410 (6)
S2—C14	1.713 (5)	C13—H13	0.9300
O1—H1A	0.8372	C5—C4	1.387 (7)
O1—H1B	0.7947	C18—H18	0.9300
O3—N1	1.244 (5)	C11—C12	1.364 (8)
O4—N1	1.252 (5)	C11—C10	1.406 (8)
O2—N1	1.214 (5)	C11—H11	0.9300
N3—C13	1.310 (5)	C1—C2	1.381 (7)
N3—C15	1.380 (5)	C1—H1	0.9300
N5—C19	1.326 (5)	C12—H12	0.9300
N5—C8	1.386 (6)	C14—H14	0.9300
N6—C16	1.271 (6)	C10—C9	1.364 (7)
N6—C17	1.391 (5)	C10—H10	0.9300
N2—C7	1.324 (5)	C9—H9	0.9300
N2—C6	1.412 (5)	C16—H16	0.9300
N7—C19	1.354 (5)	C4—C3	1.356 (8)
N7—C20	1.367 (6)	C4—H4A	0.9300
N7—H7	0.8600	C2—C3	1.420 (8)
N4—C7	1.335 (5)	C2—H2	0.9300
N4—C5	1.379 (6)	C3—H3	0.9300
N4—H4	0.8600

O1—Ni1—N3	90.37 (13)	N2—C7—C15	119.8 (4)
O1—Ni1—N5	169.10 (12)	N4—C7—C15	126.7 (4)
N3—Ni1—N5	99.19 (13)	N5—C19—N7	112.6 (4)
O1—Ni1—N2	88.88 (12)	N5—C19—C17	120.3 (3)
N3—Ni1—N2	77.42 (13)	N7—C19—C17	127.0 (4)
N5—Ni1—N2	88.12 (13)	C18—C17—N6	114.4 (4)
O1—Ni1—N6	91.69 (12)	C18—C17—C19	131.0 (4)
N3—Ni1—N6	171.22 (14)	N6—C17—C19	114.5 (3)
N5—Ni1—N6	78.08 (13)	C1—C6—C5	121.2 (4)
N2—Ni1—N6	94.09 (13)	C1—C6—N2	130.8 (4)
O1—Ni1—Cl1	91.44 (9)	C5—C6—N2	107.9 (4)
N3—Ni1—Cl1	91.99 (10)	N3—C13—S2	115.4 (4)
N5—Ni1—Cl1	93.43 (9)	N3—C13—H13	122.3
N2—Ni1—Cl1	169.41 (10)	S2—C13—H13	122.3
N6—Ni1—Cl1	96.48 (10)	N4—C5—C4	132.9 (5)
C18—S1—C16	89.2 (2)	N4—C5—C6	105.9 (4)
C13—S2—C14	89.5 (2)	C4—C5—C6	121.1 (5)
Ni1—O1—H1A	122.0	C17—C18—S1	110.3 (3)
Ni1—O1—H1B	130.8	C17—C18—H18	124.9
H1A—O1—H1B	90.7	S1—C18—H18	124.9
C13—N3—C15	110.2 (4)	C12—C11—C10	121.9 (5)
C13—N3—Ni1	134.7 (3)	C12—C11—H11	119.0
C15—N3—Ni1	115.1 (3)	C10—C11—H11	119.0
C19—N5—C8	105.7 (3)	C2—C1—C6	117.4 (5)
C19—N5—Ni1	113.7 (3)	C2—C1—H1	121.3
C8—N5—Ni1	140.4 (3)	C6—C1—H1	121.3
C16—N6—C17	111.0 (4)	C11—C12—C20	117.5 (5)
C16—N6—Ni1	135.5 (3)	C11—C12—H12	121.3
C17—N6—Ni1	113.2 (3)	C20—C12—H12	121.3
C7—N2—C6	105.0 (3)	C15—C14—S2	110.0 (4)
C7—N2—Ni1	113.3 (3)	C15—C14—H14	125.0
C6—N2—Ni1	141.4 (3)	S2—C14—H14	125.0
C19—N7—C20	107.6 (3)	C9—C10—C11	120.8 (5)
C19—N7—H7	126.2	C9—C10—H10	119.6
C20—N7—H7	126.2	C11—C10—H10	119.6
C7—N4—C5	107.6 (4)	C10—C9—C8	119.2 (5)
C7—N4—H4	126.2	C10—C9—H9	120.4
C5—N4—H4	126.2	C8—C9—H9	120.4
O2—N1—O3	120.7 (5)	N6—C16—S1	115.2 (3)
O2—N1—O4	121.6 (5)	N6—C16—H16	122.4
O3—N1—O4	117.7 (4)	S1—C16—H16	122.4
C9—C8—N5	132.1 (4)	C3—C4—C5	117.4 (5)
C9—C8—C20	119.5 (4)	C3—C4—H4A	121.3
N5—C8—C20	108.4 (4)	C5—C4—H4A	121.3
C14—C15—N3	114.9 (4)	C1—C2—C3	120.5 (5)
C14—C15—C7	130.8 (4)	C1—C2—H2	119.8
N3—C15—C7	114.3 (4)	C3—C2—H2	119.8
N7—C20—C12	133.3 (4)	C4—C3—C2	122.4 (5)
N7—C20—C8	105.7 (4)	C4—C3—H3	118.8
C12—C20—C8	121.0 (5)	C2—C3—H3	118.8
N2—C7—N4	113.5 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O3ⁱ	0.84	2.00	2.751 (5)	149
O1—H1B···O2ⁱⁱ	0.79	2.53	3.293 (6)	160
O1—H1B···O4ⁱⁱ	0.79	2.38	3.025 (5)	139
N4—H4···O3ⁱⁱⁱ	0.86	2.35	2.962 (5)	129
N4—H4···O4ⁱⁱⁱ	0.86	2.14	2.996 (5)	173
N7—H7···Cl1^iv	0.86	2.35	3.159 (4)	157

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

Experimental details

Crystal data
Chemical formula	[NiCl(C₁₀H₇N₃S)₂(H₂O)]NO₃
M_r	576.68
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	16.091 (5), 11.189 (3), 13.931 (3)
β (°)	113.275 (3)
V (Å³)	2304.1 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.18
Crystal size (mm)	0.26 × 0.25 × 0.24

Data collection
Diffractometer	Bruker SMART APEX CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.748, 0.764
No. of measured, independent and observed [I > 2σ(I)] reflections	11654, 4050, 3129
R_int	0.072
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.174, 1.07
No. of reflections	4050
No. of parameters	316
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.80, −0.53

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 1999), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O3ⁱ	0.84	2.00	2.751 (5)	149
O1—H1B···O2ⁱⁱ	0.79	2.53	3.293 (6)	160
O1—H1B···O4ⁱⁱ	0.79	2.38	3.025 (5)	139
N4—H4···O3ⁱⁱⁱ	0.86	2.35	2.962 (5)	129
N4—H4···O4ⁱⁱⁱ	0.86	2.14	2.996 (5)	173
N7—H7···Cl1^iv	0.86	2.35	3.159 (4)	157

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

Acknowledgements

This work was supported by the Key Scientific Research Projects of Guangxi University for Nationalities (2009MDZD42) and the Innovation Project of Guangxi University for Nationalities (gxun-chx2011092).

References

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