Dichlorido(ethanol-κO)[2-(1,3-thia-zol-4-yl-κN)-1H-benzimidazole-κN(3)]copper(II).

In the title complex, [CuCl(2)(C(10)H(7)N(3)S)(C(2)H(5)OH)], the Cu(II) ion is five-coordinated in a distorted square-pyramidal geometry by two N atoms from a 2-(1,3-thia-zol-4-yl)-1H-benzimidazole ligand, one O atom from an ethanol mol-ecule and two Cl atoms. In the crystal, O-H⋯Cl and N-H⋯Cl hydrogen bonds link the complex mol-ecules into a layer parallel to (100). π-π inter-actions between the thia-zole rings are observed [centroid-centroid distance = 3.749 (3) Å].

Related literature

For related thia­bendazole complexes, see: Devereux et al. (2007 ▶); Umadevi et al. (1995 ▶).

Experimental

Crystal data

[CuCl2(C10n class="Species">H7N3S)(C2H6O)]

M = 381.75

Monoclinic,

a = 13.928 (5) Å

b = 7.473 (3) Å

c = 16.653 (4) Å

β = 122.43 (2)°

V = 1463.0 (9) Å3

Z = 4

Mo Kα radiation

μ = 2.00 mm−1

T = 296 K

0.35 × 0.33 × 0.32 mm

Data collection

Bruker APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.542, T max = 0.567

7540 measured reflections

2563 independent reflections

2139 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.109

S = 1.12

2563 reflections

182 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.58 e Å−3

Δρmin = −0.32 e Å−3

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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812013037/hy2524sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812013037/hy2524Isup2.hkl

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

[CuCl2(C10H7N3S)(C2H6O)]	F(000) = 772
Mr = 381.75	Dx = 1.733 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2962 reflections
a = 13.928 (5) Å	θ = 2.5–28.0°
b = 7.473 (3) Å	µ = 2.00 mm−1
c = 16.653 (4) Å	T = 296 K
β = 122.43 (2)°	Block, blue
V = 1463.0 (9) Å3	0.35 × 0.33 × 0.32 mm
Z = 4

Bruker APEX CCD diffractometer	2563 independent reflections
Radiation source: fine-focus sealed tube	2139 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
φ and ω scans	θmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −16→16
Tmin = 0.542, Tmax = 0.567	k = −8→8
7540 measured reflections	l = −19→17

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109	H-atom parameters constrained
S = 1.12	w = 1/[σ2(Fo2) + (0.0577P)2 + 0.818P] where P = (Fo2 + 2Fc2)/3
2563 reflections	(Δ/σ)max = 0.001
182 parameters	Δρmax = 0.58 e Å−3
1 restraint	Δρmin = −0.32 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
Cu1	0.63072 (4)	0.19084 (6)	−0.14281 (3)	0.03262 (17)
Cl1	0.51582 (8)	0.09392 (13)	−0.29888 (6)	0.0417 (3)
Cl2	0.76893 (8)	0.27324 (14)	−0.16501 (7)	0.0424 (3)
S1	0.31736 (8)	0.12748 (15)	−0.12506 (7)	0.0451 (3)
O1	0.6837 (2)	−0.1091 (4)	−0.0919 (2)	0.0475 (7)
H14	0.6287	−0.1424	−0.1428	0.071*
N1	0.4997 (2)	0.1642 (4)	−0.1231 (2)	0.0323 (7)
N2	0.7045 (2)	0.2934 (4)	−0.0093 (2)	0.0305 (6)
N3	0.6867 (2)	0.3619 (4)	0.1119 (2)	0.0347 (7)
H13	0.6561	0.3739	0.1448	0.042*
C1	0.8865 (3)	0.4787 (5)	0.2244 (3)	0.0438 (9)
H1	0.8786	0.5081	0.2749	0.053*
C2	0.9871 (3)	0.5050 (5)	0.2291 (3)	0.0467 (10)
H2	1.0488	0.5528	0.2844	0.056*
C3	0.9993 (3)	0.4623 (6)	0.1540 (3)	0.0475 (10)
H3	1.0686	0.4837	0.1600	0.057*
C4	0.9115 (3)	0.3892 (6)	0.0708 (3)	0.0418 (9)
H4	0.9206	0.3601	0.0211	0.050*
C5	0.8079 (3)	0.3602 (5)	0.0638 (2)	0.0333 (8)
C6	0.7975 (3)	0.4063 (5)	0.1408 (2)	0.0342 (8)
C7	0.6359 (3)	0.2965 (4)	0.0229 (2)	0.0296 (7)
C8	0.5201 (3)	0.2321 (4)	−0.0382 (2)	0.0302 (7)
C9	0.3960 (3)	0.1024 (5)	−0.1753 (3)	0.0397 (9)
H9	0.3675	0.0496	−0.2344	0.048*
C10	0.8827 (4)	−0.1291 (9)	0.0142 (4)	0.0862 (18)
H10A	0.8844	−0.0006	0.0146	0.129*
H10B	0.9524	−0.1745	0.0235	0.129*
H10C	0.8741	−0.1709	0.0645	0.129*
C11	0.7867 (4)	−0.1919 (7)	−0.0774 (4)	0.0655 (13)
H11A	0.7975	−0.1583	−0.1283	0.079*
H11B	0.7809	−0.3212	−0.0770	0.079*
C12	0.4314 (3)	0.2252 (5)	−0.0274 (3)	0.0384 (9)
H12	0.4317	0.2673	0.0253	0.046*

	U11	U22	U33	U12	U13	U23
Cu1	0.0366 (3)	0.0378 (3)	0.0267 (3)	−0.00281 (18)	0.0191 (2)	−0.00050 (18)
Cl1	0.0483 (6)	0.0476 (6)	0.0280 (5)	−0.0005 (4)	0.0197 (4)	−0.0028 (4)
Cl2	0.0430 (5)	0.0529 (6)	0.0393 (5)	−0.0029 (4)	0.0274 (5)	0.0034 (4)
S1	0.0340 (5)	0.0540 (6)	0.0464 (6)	−0.0062 (4)	0.0211 (5)	−0.0006 (5)
O1	0.0417 (15)	0.0473 (17)	0.0467 (17)	0.0008 (12)	0.0193 (14)	0.0040 (13)
N1	0.0334 (16)	0.0382 (17)	0.0231 (15)	−0.0026 (13)	0.0137 (13)	0.0001 (12)
N2	0.0326 (15)	0.0330 (16)	0.0249 (15)	−0.0019 (12)	0.0148 (13)	0.0014 (12)
N3	0.0389 (17)	0.0408 (17)	0.0282 (16)	−0.0026 (13)	0.0205 (14)	−0.0046 (13)
C1	0.054 (2)	0.036 (2)	0.036 (2)	−0.0076 (18)	0.0208 (19)	−0.0076 (17)
C2	0.045 (2)	0.037 (2)	0.039 (2)	−0.0134 (17)	0.0101 (19)	−0.0046 (17)
C3	0.036 (2)	0.048 (2)	0.049 (2)	−0.0072 (18)	0.0173 (19)	0.005 (2)
C4	0.036 (2)	0.053 (2)	0.038 (2)	−0.0038 (17)	0.0209 (18)	0.0017 (18)
C5	0.0335 (19)	0.0355 (19)	0.027 (2)	−0.0027 (15)	0.0140 (16)	0.0004 (15)
C6	0.0348 (19)	0.0333 (19)	0.031 (2)	−0.0009 (15)	0.0156 (16)	−0.0006 (15)
C7	0.0353 (19)	0.0267 (18)	0.0276 (19)	0.0005 (14)	0.0173 (16)	0.0008 (14)
C8	0.0369 (19)	0.0245 (17)	0.0303 (19)	0.0007 (14)	0.0188 (16)	0.0046 (14)
C9	0.042 (2)	0.044 (2)	0.032 (2)	−0.0075 (17)	0.0193 (18)	−0.0026 (17)
C10	0.056 (3)	0.086 (4)	0.088 (4)	0.008 (3)	0.019 (3)	0.006 (3)
C11	0.070 (3)	0.054 (3)	0.072 (4)	0.009 (2)	0.038 (3)	0.008 (2)
C12	0.042 (2)	0.040 (2)	0.038 (2)	−0.0013 (16)	0.0257 (19)	−0.0007 (17)

Cu1—N1	2.030 (3)	C1—H1	0.9300
Cu1—N2	2.033 (3)	C2—C3	1.387 (6)
Cu1—Cl1	2.3194 (12)	C2—H2	0.9300
Cu1—Cl2	2.2328 (12)	C3—C4	1.377 (5)
Cu1—O1	2.370 (3)	C3—H3	0.9300
S1—C9	1.707 (4)	C4—C5	1.400 (5)
S1—C12	1.712 (4)	C4—H4	0.9300
O1—C11	1.459 (5)	C5—C6	1.408 (5)
O1—H14	0.8200	C7—C8	1.451 (5)
N1—C9	1.308 (5)	C8—C12	1.343 (5)
N1—C8	1.379 (5)	C9—H9	0.9300
N2—C7	1.324 (4)	C10—C11	1.466 (7)
N2—C5	1.388 (4)	C10—H10A	0.9600
N3—C7	1.346 (5)	C10—H10B	0.9600
N3—C6	1.389 (4)	C10—H10C	0.9600
N3—H13	0.8600	C11—H11A	0.9700
C1—C2	1.375 (6)	C11—H11B	0.9700
C1—C6	1.385 (5)	C12—H12	0.9300
N1—Cu1—N2	80.28 (12)	C3—C4—H4	121.1
N1—Cu1—Cl2	169.60 (9)	C5—C4—H4	121.1
N2—Cu1—Cl2	95.86 (9)	N2—C5—C4	131.8 (3)
N1—Cu1—Cl1	90.62 (9)	N2—C5—C6	108.8 (3)
N2—Cu1—Cl1	169.49 (9)	C4—C5—C6	119.4 (3)
Cl2—Cu1—Cl1	92.21 (4)	C1—C6—N3	132.1 (3)
N1—Cu1—O1	89.08 (10)	C1—C6—C5	122.5 (3)
N2—Cu1—O1	95.01 (11)	N3—C6—C5	105.4 (3)
Cl2—Cu1—O1	100.92 (7)	N2—C7—N3	112.7 (3)
Cl1—Cu1—O1	90.06 (8)	N2—C7—C8	118.8 (3)
C9—S1—C12	90.03 (18)	N3—C7—C8	128.5 (3)
C11—O1—Cu1	123.4 (3)	C12—C8—N1	115.1 (3)
C11—O1—H14	109.5	C12—C8—C7	132.4 (3)
Cu1—O1—H14	88.7	N1—C8—C7	112.5 (3)
C9—N1—C8	111.0 (3)	N1—C9—S1	114.0 (3)
C9—N1—Cu1	134.1 (3)	N1—C9—H9	123.0
C8—N1—Cu1	114.8 (2)	S1—C9—H9	123.0
C7—N2—C5	105.8 (3)	C11—C10—H10A	109.5
C7—N2—Cu1	113.5 (2)	C11—C10—H10B	109.5
C5—N2—Cu1	140.6 (2)	H10A—C10—H10B	109.5
C7—N3—C6	107.3 (3)	C11—C10—H10C	109.5
C7—N3—H13	126.3	H10A—C10—H10C	109.5
C6—N3—H13	126.4	H10B—C10—H10C	109.5
C2—C1—C6	116.6 (4)	O1—C11—C10	107.6 (4)
C2—C1—H1	121.7	O1—C11—H11A	110.2
C6—C1—H1	121.7	C10—C11—H11A	110.2
C1—C2—C3	122.0 (4)	O1—C11—H11B	110.2
C1—C2—H2	119.0	C10—C11—H11B	110.2
C3—C2—H2	119.0	H11A—C11—H11B	108.5
C4—C3—C2	121.7 (4)	C8—C12—S1	109.9 (3)
C4—C3—H3	119.1	C8—C12—H12	125.1
C2—C3—H3	119.1	S1—C12—H12	125.1
C3—C4—C5	117.7 (4)
N1—Cu1—O1—C11	−174.0 (3)	C2—C1—C6—N3	179.7 (4)
N2—Cu1—O1—C11	−93.8 (3)	C2—C1—C6—C5	0.3 (6)
Cl2—Cu1—O1—C11	3.1 (3)	C7—N3—C6—C1	179.7 (4)
Cl1—Cu1—O1—C11	95.4 (3)	C7—N3—C6—C5	−0.8 (4)
N2—Cu1—N1—C9	179.9 (4)	N2—C5—C6—C1	−179.3 (3)
Cl2—Cu1—N1—C9	111.0 (5)	C4—C5—C6—C1	−0.5 (6)
Cl1—Cu1—N1—C9	5.2 (3)	N2—C5—C6—N3	1.1 (4)
O1—Cu1—N1—C9	−84.9 (4)	C4—C5—C6—N3	180.0 (3)
N2—Cu1—N1—C8	3.3 (2)	C5—N2—C7—N3	0.4 (4)
Cl2—Cu1—N1—C8	−65.6 (6)	Cu1—N2—C7—N3	178.9 (2)
Cl1—Cu1—N1—C8	−171.4 (2)	C5—N2—C7—C8	−179.4 (3)
O1—Cu1—N1—C8	98.5 (2)	Cu1—N2—C7—C8	−0.9 (4)
N1—Cu1—N2—C7	−1.2 (2)	C6—N3—C7—N2	0.3 (4)
Cl2—Cu1—N2—C7	169.0 (2)	C6—N3—C7—C8	−179.9 (3)
Cl1—Cu1—N2—C7	29.1 (6)	C9—N1—C8—C12	−1.4 (4)
O1—Cu1—N2—C7	−89.4 (2)	Cu1—N1—C8—C12	175.9 (2)
N1—Cu1—N2—C5	176.5 (4)	C9—N1—C8—C7	178.1 (3)
Cl2—Cu1—N2—C5	−13.2 (4)	Cu1—N1—C8—C7	−4.5 (4)
Cl1—Cu1—N2—C5	−153.1 (4)	N2—C7—C8—C12	−177.0 (4)
O1—Cu1—N2—C5	88.3 (4)	N3—C7—C8—C12	3.2 (6)
C6—C1—C2—C3	0.3 (6)	N2—C7—C8—N1	3.7 (4)
C1—C2—C3—C4	−0.8 (7)	N3—C7—C8—N1	−176.2 (3)
C2—C3—C4—C5	0.6 (6)	C8—N1—C9—S1	1.2 (4)
C7—N2—C5—C4	−179.6 (4)	Cu1—N1—C9—S1	−175.49 (19)
Cu1—N2—C5—C4	2.5 (7)	C12—S1—C9—N1	−0.6 (3)
C7—N2—C5—C6	−0.9 (4)	Cu1—O1—C11—C10	78.2 (5)
Cu1—N2—C5—C6	−178.8 (3)	N1—C8—C12—S1	1.0 (4)
C3—C4—C5—N2	178.6 (4)	C7—C8—C12—S1	−178.4 (3)
C3—C4—C5—C6	0.0 (5)	C9—S1—C12—C8	−0.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H14···Cl1i	0.82	2.60	3.246 (3)	136
N3—H13···Cl1ii	0.86	2.59	3.431 (4)	165

Table 1

Selected bond lengths (Å)

Cu1—N1	2.030 (3)
Cu1—N2	2.033 (3)
Cu1—Cl1	2.3194 (12)
Cu1—Cl2	2.2328 (12)
Cu1—O1	2.370 (3)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H14⋯Cl1i	0.82	2.60	3.246 (3)	136
N3—H13⋯Cl1ii	0.86	2.59	3.431 (4)	165

Symmetry codes: (i) ; (ii) .