Aquachloridobis[2-(1,3-thia-zol-4-yl-κN)-1H-benzimidazole-κN(3)]nickel(II) nitrate.

In the title compound, [NiCl(C(10)H(7)N(3)S)(2)(H(2)O)]NO(3), the Ni(II) ion is coordinated by four N atoms from two chelating 2-(1,3-thia-zol-4-yl)-1H-benzimidazole ligands, one Cl atom and one water mol-ecule in a distorted octa-hedral 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 inter-actions between the thia-zole and imidazole rings and between the thia-zole 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 = 576.68

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.174

S = 1.07

4050 reflections

316 parameters

H-atom parameters constrained

Δρmax = 0.80 e Å−3

Δρmin = −0.53 e Å−3

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 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812029728/hy2553sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812029728/hy2553Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[NiCl(C10H7N3S)2(H2O)]NO3	F(000) = 1176
Mr = 576.68	Dx = 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

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

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(Fo2) + (0.083P)2 + 1.4424P] where P = (Fo2 + 2Fc2)/3
4050 reflections	(Δ/σ)max = 0.045
316 parameters	Δρmax = 0.80 e Å−3
0 restraints	Δρmin = −0.53 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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···Cl1iv	0.86	2.35	3.159 (4)	157

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⋯Cl1iv	0.86	2.35	3.159 (4)	157

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .