Dichlorido(ethanol-κO)[2-(1,3-thia­zol-4-yl-κN)-1H-benzimidazole-κN3]copper(II)

Li, L.; Diao, K.-S.; Ding, Y.-Q.; Tang, J.-N.; Wang, D.-Y.

doi:10.1107/S1600536812013037

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 4| April 2012| Page m508

doi:10.1107/S1600536812013037

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Dichlorido(ethanol-κO)[2-(1,3-thiazol-4-yl-κN)-1H-benzimidazole-κN³]copper(II)

Long Li,^a Kai-Sheng Diao,^a,^b ^* Yu-Qiu Ding,^a Jin-Niu Tang ^a and Dai-Yin Wang ^a

^aCollege of Chemistry and Chemical Engineering, Guangxi University for Nationalities, Nanning 530006, People's Republic of China, and ^bKey Laboratory of Development & Application of Forest Chemicals of Guangxi, Nanning 530006, People's Republic of China
^*Correspondence e-mail: 497426630@qq.com

(Received 10 March 2012; accepted 25 March 2012; online 31 March 2012)

In the title complex, [CuCl₂(C₁₀H₇N₃S)(C₂H₅OH)], the Cu^II ion is five-coordinated in a distorted square-pyramidal geometry by two N atoms from a 2-(1,3-thiazol-4-yl)-1H-benzimidazole ligand, one O atom from an ethanol molecule and two Cl atoms. In the crystal, O—H⋯Cl and N—H⋯Cl hydrogen bonds link the complex molecules into a layer parallel to (100). π–π interactions between the thiazole 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(C₁₀H₇N₃S)(C₂H₆O)]
M_r = 381.75
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.034
wR(F²) = 0.109
S = 1.12
2563 reflections
182 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.58 e Å⁻³
Δρ_min = −0.32 e Å⁻³

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) $[-x+1, y-{\script{1\over 2}}, -z-{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

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).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812013037/hy2524sup1.cif

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

checkCIF report

Comment top

As we know, thiabendazole, 2-(4-thiazolyl)benzimidazole, is widely used as a kind of anthelmintic. However, the insolubility in water restrict its potential efficacy. Thiabendazole has three N and one S atoms, easy to coordinate with non-toxic metals (Devereux et al., 2007; Umadevi et al., 1995). These metal-organic compounds would be more water soluble, yet retain the biological activity of the base. As part of our studies of researching the properties and effects of metal complexes of thiabendazole, we have synthesized the title compound.

In the title complex (Fig. 1), the Cu^II ion is five-coordinated in a distorted square-pyramidal geometry by two N atoms from a 1H-2-(4-thiazol-2-yl)benzimidazole ligand, one O atom from an ethanol molecule and two Cl atoms (Table 1). The dihedral angle between the imidazole ring (C5, C6, C7, N2, N3) and the thiazole ring (N1, S1, C8, C9, C12) is 3.8 (1)°. O—H···Cl and N—H···Cl hydrogen bonds link the complex molecules into a layer parallel to (100) (Fig. 2, Table 2). π–π interactions between the thiazole rings are observed [centroid–centroid distance = 3.749 (3) Å].

Related literature top

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

Experimental top

The title compound was prepared by the reaction of thiabendazole (1.5 mol) with cupric chloride (1 mol) in ethanol, with stirring at 343 K for 5 h and then filtered. The filtrate was kept at room temperature and three days later X-ray quality blue block-shaped single crystals were obtained.

Structure description top

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

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: SHELXTL (Sheldrick, 2008); 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.
	Fig. 2. The crystal packing diagram of the title compound.

Dichlorido(ethanol-κO)[2-(1,3-thiazol-4-yl-κN)-1H- benzimidazole-κN³]copper(II) top

Crystal data top

[CuCl₂(C₁₀H₇N₃S)(C₂H₆O)]	F(000) = 772
M_r = 381.75	D_x = 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

Data collection top

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

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.109	H-atom parameters constrained
S = 1.12	w = 1/[σ²(F_o²) + (0.0577P)² + 0.818P] where P = (F_o² + 2F_c²)/3
2563 reflections	(Δ/σ)_max = 0.001
182 parameters	Δρ_max = 0.58 e Å⁻³
1 restraint	Δρ_min = −0.32 e Å⁻³

Crystal data top

[CuCl₂(C₁₀H₇N₃S)(C₂H₆O)]	V = 1463.0 (9) Å³
M_r = 381.75	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.928 (5) Å	µ = 2.00 mm⁻¹
b = 7.473 (3) Å	T = 296 K
c = 16.653 (4) Å	0.35 × 0.33 × 0.32 mm
β = 122.43 (2)°

Data collection top

Bruker APEX CCD diffractometer	2563 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2139 reflections with I > 2σ(I)
T_min = 0.542, T_max = 0.567	R_int = 0.036
7540 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	1 restraint
wR(F²) = 0.109	H-atom parameters constrained
S = 1.12	Δρ_max = 0.58 e Å⁻³
2563 reflections	Δρ_min = −0.32 e Å⁻³
182 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
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, y−1/2, −z−1/2; (ii) x, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	[CuCl₂(C₁₀H₇N₃S)(C₂H₆O)]
M_r	381.75
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	13.928 (5), 7.473 (3), 16.653 (4)
β (°)	122.43 (2)
V (Å³)	1463.0 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.00
Crystal size (mm)	0.35 × 0.33 × 0.32

Data collection
Diffractometer	Bruker APEX CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.542, 0.567
No. of measured, independent and observed [I > 2σ(I)] reflections	7540, 2563, 2139
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.109, 1.12
No. of reflections	2563
No. of parameters	182
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.58, −0.32

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

Selected bond lengths (Å) top

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

Hydrogen-bond geometry (Å, º) top

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) −x+1, y−1/2, −z−1/2; (ii) x, −y+1/2, z+1/2.

Acknowledgements

This work was supported financially by the Scientific Research Program of the Education Department of Guangxi Zhuang Autonomous Region (project No. 201010LX081) and the Scientific Research Program of Guangxi University for Nationalities (project No. 2010QD019).

References

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