Chloridobis[2-(1,3-thia­zol-4-yl-κN)-1H-benzimidazole-κN3]cobalt(II) chloride dihydrate

Shi, Z.-W.; Qin, Y.; Lin, Y.-X.; Wu, W.; Liang, P.

doi:10.1107/S1600536812030371

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 8| August 2012| Pages m1042-m1043

https://doi.org/10.1107/S1600536812030371

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Chloridobis[2-(1,3-thiazol-4-yl-κN)-1H-benzimidazole-κN³]cobalt(II) chloride dihydrate

Zhan-Wang Shi,^a ^* Yan Qin,^a Yan-Xia Lin,^b Wei Wu ^a and Peng Liang ^a

^aDepartment of Chemistry and Chemical Engineering, Guangxi University for Nationalities, Nanning 530006, People's Republic of China, and ^bHybio Pharmaceutical Co. Ltd, Shenzhen 518057, People's Republic of China
^*Correspondence e-mail: 6628yxh@163.com

(Received 18 June 2012; accepted 3 July 2012; online 10 July 2012)

In the title compound, [CoCl(C₁₀H₇N₃S)₂]Cl·2H₂O, the Co^II atom is five-coordinated by four N atoms from two chelating 2-(1,3-thiazol-4-yl)-1H-benzimidazole ligands and one Cl atom in a distorted trigonal–bipyramidal geometry. In the crystal, N—H⋯O and O—H⋯Cl hydrogen bonds and π–π interactions between the thiazole, imidazole and benzene rings [centroid-to-centroid distances 3.546 (2), 3.683 (2) and 3.714 (2) Å] link the complex cations, chloride anions and uncoordinating water molecules into a three-dimensional network.

Related literature

For related structures, see: Devereux et al. (2004 , 2007 ); Flores-Alamo et al. (2010 ); Jean et al. (2002 ); Mothilal et al. (2004 ); Murugesan et al. (1998 ); Ren et al. (2010 ); Stanley et al. (2002 ); Trus & Marsh (1973 ); Wisniewski et al. (2001 ).

Experimental

Crystal data

[CoCl(C₁₀H₇N₃S)₂]Cl·2H₂O
M_r = 568.35
Monoclinic, P 2₁ /c
a = 14.803 (4) Å
b = 11.709 (3) Å
c = 14.082 (4) Å
β = 101.439 (4)°
V = 2392.3 (11) Å³
Z = 4
Mo Kα radiation
μ = 1.15 mm⁻¹
T = 296 K
0.20 × 0.20 × 0.20 mm

Data collection

Bruker SMART 1000 CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.803, T_max = 0.803
12683 measured reflections
4200 independent reflections
3517 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.096
S = 1.05
4200 reflections
298 parameters
H-atom parameters constrained
Δρ_max = 0.52 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯O2ⁱ	0.86	1.90	2.748 (3)	169
N6—H6⋯O1	0.86	1.86	2.704 (3)	168
O1—H1B⋯Cl2ⁱⁱ	0.85	2.27	3.104 (3)	169
O1—H1A⋯Cl1ⁱⁱⁱ	0.85	2.43	3.272 (3)	169
O2—H2B⋯Cl1	0.85	2.45	3.296 (3)	171
O2—H2A⋯Cl2	0.85	2.21	3.052 (2)	174
Symmetry codes: (i) $[-x, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) -x+1, -y+1, -z+2.

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/S1600536812030371/hy2563sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812030371/hy2563Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812030371/hy2563Isup3.cdx

checkCIF report

Comment top

Metal-based drugs aroused considerable interest in biology and medicine due to their antiproliferative activities. Thiabendazole is an antimicrobial drug belonging to the benzimidazole derivatives and exhibits wide applications in human and veterinary medicine. Thiabendazole had been studied for a long time. The crystal structures of thiabendazole (Trus & Marsh, 1973), thiabendazolium nitrate (Murugesan et al., 1998), thiabendazolium chlorate (Stanley et al., 2002), and a lot of its metal compounds (Devereux et al., 2004, 2007; Flores-Alamo et al., 2010; Jean et al., 2002; Mothilal et al., 2004; Ren et al., 2010; Wisniewski et al., 2001) have been reported.

The title compound consists of a complex cation, a Cl^- anion and two uncoordinated water molecules (Fig. 1). The Co^II atom is five-coordinated by four N atoms from two chelating 2-(1,3-thiazol-4-yl)-1H-benzimidazole ligands and one Cl atom in a distorted trigonal-bipyramidal geometry. In the crystal, N—H···O and O—H···Cl hydrogen bonds (Table 1) and π–π interactions between the thiazole, imidazole and benzene rings [centroid–centroid distances = 3.546 (2), 3.683 (2) and 3.714 (2) Å] link the cations, anions and water molecules into a three-dimensional network.

Related literature top

For related structures, see: Devereux et al. (2004, 2007); Flores-Alamo et al. (2010); Jean et al. (2002); Mothilal et al. (2004); Murugesan et al. (1998); Ren et al. (2010); Stanley et al. (2002); Trus & Marsh (1973); Wisniewski et al. (2001).

Experimental top

In a 100 ml flask, thiabendazole hydrochloride (0.237 g, 1 mmol) and CoCl₂.6H₂O (0.240 g, 1 mmol) were dissolved in 20 ml water, 20 ml EtOH and 5 ml DMF. The mixture was heated to 350 K for 5 h. After cooling to room temperature, the mixture was filtered and the filtrate was evaporated slowly. After a month, red crystals were collected and washed with water (yield: 0.198 g, 34.9% based on Co).

Structure description top

For related structures, see: Devereux et al. (2004, 2007); Flores-Alamo et al. (2010); Jean et al. (2002); Mothilal et al. (2004); Murugesan et al. (1998); Ren et al. (2010); Stanley et al. (2002); Trus & Marsh (1973); Wisniewski et al. (2001).

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, showing 50% probability ellipsoids. H atoms have been omitted for clarity.
	Fig. 2. Crystal packing of the title compound, showing the molecules connected by O—H···Cl and N—H···O hydrogen bonds (dashed lines).

Chloridobis[2-(1,3-thiazol-4-yl-κN)-1H-benzimidazole- κN³]cobalt(II) chloride dihydrate top

Crystal data top

[CoCl(C₁₀H₇N₃S)₂]Cl·2H₂O	F(000) = 1156
M_r = 568.35	D_x = 1.578 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5625 reflections
a = 14.803 (4) Å	θ = 2.5–27.9°
b = 11.709 (3) Å	µ = 1.15 mm⁻¹
c = 14.082 (4) Å	T = 296 K
β = 101.439 (4)°	Block, red
V = 2392.3 (11) Å³	0.20 × 0.20 × 0.20 mm
Z = 4

Data collection top

Bruker SMART 1000 CCD diffractometer	4200 independent reflections
Radiation source: fine-focus sealed tube	3517 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
φ and ω scans	θ_max = 25.0°, θ_min = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→17
T_min = 0.803, T_max = 0.803	k = −13→13
12683 measured reflections	l = −16→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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.096	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0452P)² + 1.5251P] where P = (F_o² + 2F_c²)/3
4200 reflections	(Δ/σ)_max < 0.001
298 parameters	Δρ_max = 0.52 e Å⁻³
0 restraints	Δρ_min = −0.37 e Å⁻³

Crystal data top

[CoCl(C₁₀H₇N₃S)₂]Cl·2H₂O	V = 2392.3 (11) Å³
M_r = 568.35	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.803 (4) Å	µ = 1.15 mm⁻¹
b = 11.709 (3) Å	T = 296 K
c = 14.082 (4) Å	0.20 × 0.20 × 0.20 mm
β = 101.439 (4)°

Data collection top

Bruker SMART 1000 CCD diffractometer	4200 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3517 reflections with I > 2σ(I)
T_min = 0.803, T_max = 0.803	R_int = 0.029
12683 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.096	H-atom parameters constrained
S = 1.05	Δρ_max = 0.52 e Å⁻³
4200 reflections	Δρ_min = −0.37 e Å⁻³
298 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
Co1	0.24191 (2)	0.52351 (3)	0.80442 (2)	0.03535 (12)
N1	0.12865 (16)	0.48857 (19)	0.70875 (17)	0.0431 (5)
N2	0.19207 (15)	0.69958 (19)	0.75929 (16)	0.0439 (5)
N3	−0.00486 (16)	0.54257 (19)	0.62029 (16)	0.0445 (5)
H3	−0.0486	0.5863	0.5919	0.053*
N4	0.36009 (15)	0.57629 (19)	0.88293 (17)	0.0433 (5)
N5	0.32957 (16)	0.4841 (2)	0.70910 (17)	0.0463 (6)
N6	0.50953 (15)	0.60834 (19)	0.89573 (16)	0.0427 (5)
H6	0.5629	0.6109	0.8805	0.051*
O1	0.68432 (15)	0.6368 (2)	0.86990 (18)	0.0747 (7)
H1A	0.7236	0.6088	0.9164	0.090*
H1B	0.6967	0.6135	0.8168	0.090*
O2	0.15760 (14)	0.17298 (19)	0.95087 (16)	0.0608 (6)
H2A	0.1934	0.1473	0.9156	0.073*
H2B	0.1578	0.2455	0.9482	0.073*
S1	0.42099 (6)	0.43913 (9)	0.57955 (7)	0.0668 (3)
S2	0.14108 (6)	0.90259 (6)	0.71020 (6)	0.0563 (2)
Cl1	0.18070 (6)	0.45144 (7)	0.93089 (6)	0.0572 (2)
Cl2	0.29471 (6)	0.07173 (8)	0.83834 (7)	0.0652 (2)
C1	0.39292 (18)	0.6275 (2)	0.9725 (2)	0.0430 (6)
C2	0.3493 (2)	0.6578 (3)	1.0480 (2)	0.0565 (8)
H2	0.2865	0.6460	1.0436	0.068*
C3	0.4030 (2)	0.7058 (3)	1.1293 (2)	0.0637 (9)
H3A	0.3757	0.7268	1.1807	0.076*
C4	0.4968 (2)	0.7237 (3)	1.1363 (2)	0.0573 (8)
H4	0.5305	0.7565	1.1925	0.069*
C5	0.5412 (2)	0.6952 (2)	1.0641 (2)	0.0499 (7)
H5	0.6040	0.7076	1.0695	0.060*
C6	0.48778 (18)	0.6465 (2)	0.98172 (19)	0.0409 (6)
C7	0.43232 (18)	0.5669 (2)	0.84080 (19)	0.0407 (6)
C8	0.41976 (19)	0.5164 (2)	0.7457 (2)	0.0416 (6)
C9	0.4787 (2)	0.4974 (3)	0.6854 (2)	0.0520 (7)
H9	0.5414	0.5137	0.6996	0.062*
C10	0.3214 (2)	0.4410 (3)	0.6220 (2)	0.0599 (8)
H10	0.2658	0.4138	0.5865	0.072*
C11	0.08023 (19)	0.3911 (2)	0.6733 (2)	0.0436 (6)
C12	0.1039 (2)	0.2764 (3)	0.6844 (2)	0.0547 (7)
H12	0.1600	0.2529	0.7214	0.066*
C13	0.0396 (3)	0.1989 (3)	0.6377 (3)	0.0637 (9)
H13	0.0535	0.1214	0.6428	0.076*
C14	−0.0449 (3)	0.2327 (3)	0.5835 (2)	0.0628 (9)
H14	−0.0865	0.1772	0.5548	0.075*
C15	−0.0687 (2)	0.3454 (3)	0.5711 (2)	0.0545 (8)
H15	−0.1250	0.3680	0.5339	0.065*
C16	−0.00419 (19)	0.4249 (2)	0.61717 (19)	0.0425 (6)
C17	0.07502 (18)	0.5765 (2)	0.67555 (19)	0.0403 (6)
C18	0.10696 (18)	0.6918 (2)	0.69648 (19)	0.0423 (6)
C19	0.0698 (2)	0.7934 (2)	0.6639 (2)	0.0521 (7)
H19	0.0132	0.8024	0.6221	0.063*
C20	0.2169 (2)	0.8065 (2)	0.7725 (2)	0.0484 (7)
H20	0.2718	0.8284	0.8128	0.058*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co1	0.02582 (19)	0.0390 (2)	0.0398 (2)	−0.00224 (13)	0.00312 (14)	−0.00274 (14)
N1	0.0372 (12)	0.0425 (13)	0.0489 (13)	−0.0005 (10)	0.0068 (10)	0.0016 (10)
N2	0.0379 (12)	0.0443 (13)	0.0486 (13)	0.0001 (10)	0.0065 (10)	−0.0020 (10)
N3	0.0375 (12)	0.0488 (14)	0.0441 (13)	0.0003 (10)	0.0007 (10)	0.0059 (10)
N4	0.0344 (12)	0.0449 (13)	0.0497 (13)	−0.0011 (10)	0.0064 (10)	−0.0044 (10)
N5	0.0364 (12)	0.0513 (14)	0.0491 (14)	−0.0013 (10)	0.0033 (10)	−0.0072 (11)
N6	0.0341 (12)	0.0482 (13)	0.0450 (13)	−0.0057 (10)	0.0055 (10)	0.0002 (10)
O1	0.0463 (13)	0.1013 (19)	0.0761 (16)	−0.0047 (13)	0.0114 (11)	0.0041 (14)
O2	0.0544 (13)	0.0559 (13)	0.0701 (14)	−0.0024 (10)	0.0072 (11)	−0.0076 (11)
S1	0.0620 (5)	0.0828 (6)	0.0582 (5)	−0.0049 (4)	0.0180 (4)	−0.0234 (4)
S2	0.0639 (5)	0.0412 (4)	0.0634 (5)	0.0021 (3)	0.0121 (4)	0.0026 (3)
Cl1	0.0574 (5)	0.0584 (5)	0.0558 (4)	−0.0100 (4)	0.0112 (4)	0.0053 (3)
Cl2	0.0516 (5)	0.0696 (5)	0.0732 (5)	−0.0039 (4)	0.0096 (4)	−0.0142 (4)
C1	0.0428 (15)	0.0374 (14)	0.0481 (15)	−0.0033 (12)	0.0074 (12)	−0.0040 (12)
C2	0.0489 (17)	0.0591 (19)	0.064 (2)	−0.0050 (14)	0.0161 (15)	−0.0134 (15)
C3	0.072 (2)	0.062 (2)	0.060 (2)	−0.0073 (17)	0.0206 (17)	−0.0183 (16)
C4	0.067 (2)	0.0513 (18)	0.0500 (17)	−0.0102 (15)	0.0022 (15)	−0.0114 (14)
C5	0.0502 (17)	0.0418 (16)	0.0540 (17)	−0.0086 (13)	0.0017 (14)	−0.0009 (13)
C6	0.0422 (15)	0.0365 (14)	0.0422 (15)	−0.0023 (11)	0.0040 (12)	0.0009 (11)
C7	0.0383 (14)	0.0383 (14)	0.0441 (15)	−0.0007 (11)	0.0049 (12)	0.0017 (11)
C8	0.0377 (14)	0.0399 (14)	0.0465 (15)	−0.0012 (11)	0.0068 (12)	0.0021 (12)
C9	0.0439 (16)	0.0540 (17)	0.0602 (19)	−0.0032 (13)	0.0155 (14)	−0.0054 (14)
C10	0.0512 (18)	0.070 (2)	0.0560 (19)	−0.0053 (16)	0.0051 (15)	−0.0192 (16)
C11	0.0408 (15)	0.0463 (16)	0.0448 (15)	−0.0032 (12)	0.0111 (12)	0.0000 (12)
C12	0.0535 (18)	0.0493 (17)	0.0613 (19)	0.0034 (14)	0.0110 (15)	0.0033 (14)
C13	0.077 (2)	0.0449 (18)	0.072 (2)	−0.0066 (16)	0.0224 (19)	−0.0007 (15)
C14	0.077 (2)	0.055 (2)	0.0586 (19)	−0.0255 (17)	0.0189 (18)	−0.0063 (15)
C15	0.0516 (18)	0.067 (2)	0.0447 (16)	−0.0163 (15)	0.0076 (13)	−0.0009 (14)
C16	0.0414 (15)	0.0493 (16)	0.0370 (14)	−0.0069 (12)	0.0080 (12)	0.0004 (12)
C17	0.0375 (14)	0.0443 (15)	0.0394 (14)	−0.0005 (12)	0.0081 (11)	0.0021 (11)
C18	0.0411 (15)	0.0460 (16)	0.0390 (14)	0.0004 (12)	0.0064 (12)	0.0006 (12)
C19	0.0536 (17)	0.0484 (17)	0.0523 (17)	0.0048 (14)	0.0051 (14)	0.0033 (13)
C20	0.0451 (16)	0.0449 (17)	0.0551 (17)	−0.0025 (13)	0.0100 (13)	−0.0057 (13)

Geometric parameters (Å, º) top

Co1—N1	1.974 (2)	C1—C6	1.402 (4)
Co1—N4	1.974 (2)	C2—C3	1.377 (4)
Co1—N5	2.095 (2)	C2—H2	0.9300
Co1—N2	2.239 (2)	C3—C4	1.390 (5)
Co1—Cl1	2.3120 (9)	C3—H3A	0.9300
N1—C17	1.327 (4)	C4—C5	1.357 (4)
N1—C11	1.387 (4)	C4—H4	0.9300
N2—C20	1.308 (4)	C5—C6	1.391 (4)
N2—C18	1.391 (3)	C5—H5	0.9300
N3—C17	1.340 (3)	C7—C8	1.442 (4)
N3—C16	1.379 (4)	C8—C9	1.351 (4)
N3—H3	0.8600	C9—H9	0.9300
N4—C7	1.326 (3)	C10—H10	0.9300
N4—C1	1.393 (3)	C11—C12	1.389 (4)
N5—C10	1.310 (4)	C11—C16	1.397 (4)
N5—C8	1.385 (4)	C12—C13	1.383 (4)
N6—C7	1.338 (3)	C12—H12	0.9300
N6—C6	1.387 (3)	C13—C14	1.388 (5)
N6—H6	0.8600	C13—H13	0.9300
O1—H1A	0.8500	C14—C15	1.368 (5)
O1—H1B	0.8500	C14—H14	0.9300
O2—H2A	0.8500	C15—C16	1.398 (4)
O2—H2B	0.8500	C15—H15	0.9300
S1—C10	1.698 (3)	C17—C18	1.442 (4)
S1—C9	1.707 (3)	C18—C19	1.352 (4)
S2—C19	1.702 (3)	C19—H19	0.9300
S2—C20	1.704 (3)	C20—H20	0.9300
C1—C2	1.395 (4)

N1—Co1—N4	170.18 (10)	C6—C5—H5	121.7
N1—Co1—N5	93.86 (9)	N6—C6—C5	132.0 (3)
N4—Co1—N5	80.51 (9)	N6—C6—C1	105.6 (2)
N1—Co1—N2	79.03 (9)	C5—C6—C1	122.4 (3)
N4—Co1—N2	94.37 (9)	N4—C7—N6	112.5 (2)
N5—Co1—N2	103.42 (9)	N4—C7—C8	118.9 (2)
N1—Co1—Cl1	92.32 (7)	N6—C7—C8	128.6 (2)
N4—Co1—Cl1	97.01 (7)	C9—C8—N5	114.6 (3)
N5—Co1—Cl1	143.16 (7)	C9—C8—C7	132.1 (3)
N2—Co1—Cl1	113.41 (6)	N5—C8—C7	113.2 (2)
C17—N1—C11	106.3 (2)	C8—C9—S1	109.9 (2)
C17—N1—Co1	116.58 (19)	C8—C9—H9	125.0
C11—N1—Co1	136.43 (19)	S1—C9—H9	125.0
C20—N2—C18	110.3 (2)	N5—C10—S1	114.1 (2)
C20—N2—Co1	140.7 (2)	N5—C10—H10	122.9
C18—N2—Co1	109.04 (17)	S1—C10—H10	122.9
C17—N3—C16	107.7 (2)	N1—C11—C12	130.9 (3)
C17—N3—H3	126.2	N1—C11—C16	108.1 (2)
C16—N3—H3	126.2	C12—C11—C16	121.0 (3)
C7—N4—C1	105.8 (2)	C13—C12—C11	116.5 (3)
C7—N4—Co1	115.27 (18)	C13—C12—H12	121.7
C1—N4—Co1	138.82 (18)	C11—C12—H12	121.7
C10—N5—C8	110.9 (2)	C12—C13—C14	122.3 (3)
C10—N5—Co1	136.9 (2)	C12—C13—H13	118.8
C8—N5—Co1	112.05 (18)	C14—C13—H13	118.8
C7—N6—C6	107.6 (2)	C15—C14—C13	121.8 (3)
C7—N6—H6	126.2	C15—C14—H14	119.1
C6—N6—H6	126.2	C13—C14—H14	119.1
H1A—O1—H1B	108.7	C14—C15—C16	116.6 (3)
H2A—O2—H2B	108.7	C14—C15—H15	121.7
C10—S1—C9	90.38 (15)	C16—C15—H15	121.7
C19—S2—C20	89.78 (15)	N3—C16—C11	106.0 (2)
N4—C1—C2	131.9 (3)	N3—C16—C15	132.2 (3)
N4—C1—C6	108.4 (2)	C11—C16—C15	121.8 (3)
C2—C1—C6	119.7 (3)	N1—C17—N3	111.9 (2)
C3—C2—C1	117.4 (3)	N1—C17—C18	120.4 (2)
C3—C2—H2	121.3	N3—C17—C18	127.7 (2)
C1—C2—H2	121.3	C19—C18—N2	114.5 (3)
C2—C3—C4	121.6 (3)	C19—C18—C17	131.3 (3)
C2—C3—H3A	119.2	N2—C18—C17	114.2 (2)
C4—C3—H3A	119.2	C18—C19—S2	110.6 (2)
C5—C4—C3	122.4 (3)	C18—C19—H19	124.7
C5—C4—H4	118.8	S2—C19—H19	124.7
C3—C4—H4	118.8	N2—C20—S2	114.9 (2)
C4—C5—C6	116.5 (3)	N2—C20—H20	122.5
C4—C5—H5	121.7	S2—C20—H20	122.5

N5—Co1—N1—C17	−110.9 (2)	C10—N5—C8—C9	0.1 (4)
N2—Co1—N1—C17	−7.97 (19)	Co1—N5—C8—C9	−177.3 (2)
Cl1—Co1—N1—C17	105.44 (19)	C10—N5—C8—C7	178.7 (3)
N5—Co1—N1—C11	80.0 (3)	Co1—N5—C8—C7	1.3 (3)
N2—Co1—N1—C11	−177.0 (3)	N4—C7—C8—C9	178.9 (3)
Cl1—Co1—N1—C11	−63.6 (3)	N6—C7—C8—C9	−0.7 (5)
N1—Co1—N2—C20	−174.8 (3)	N4—C7—C8—N5	0.6 (4)
N4—Co1—N2—C20	−2.2 (3)	N6—C7—C8—N5	−179.0 (3)
N5—Co1—N2—C20	−83.5 (3)	N5—C8—C9—S1	0.6 (3)
Cl1—Co1—N2—C20	97.4 (3)	C7—C8—C9—S1	−177.6 (3)
N1—Co1—N2—C18	4.89 (17)	C10—S1—C9—C8	−0.9 (3)
N4—Co1—N2—C18	177.54 (17)	C8—N5—C10—S1	−0.9 (4)
N5—Co1—N2—C18	96.27 (18)	Co1—N5—C10—S1	175.71 (17)
Cl1—Co1—N2—C18	−82.88 (17)	C9—S1—C10—N5	1.0 (3)
N5—Co1—N4—C7	2.24 (19)	C17—N1—C11—C12	179.2 (3)
N2—Co1—N4—C7	−100.7 (2)	Co1—N1—C11—C12	−11.0 (5)
Cl1—Co1—N4—C7	145.09 (19)	C17—N1—C11—C16	0.4 (3)
N5—Co1—N4—C1	178.8 (3)	Co1—N1—C11—C16	170.2 (2)
N2—Co1—N4—C1	75.9 (3)	N1—C11—C12—C13	−179.0 (3)
Cl1—Co1—N4—C1	−38.4 (3)	C16—C11—C12—C13	−0.3 (4)
N1—Co1—N5—C10	−6.5 (3)	C11—C12—C13—C14	−0.9 (5)
N4—Co1—N5—C10	−178.4 (3)	C12—C13—C14—C15	1.7 (5)
N2—Co1—N5—C10	−86.2 (3)	C13—C14—C15—C16	−1.1 (5)
Cl1—Co1—N5—C10	92.5 (3)	C17—N3—C16—C11	−0.1 (3)
N1—Co1—N5—C8	170.01 (19)	C17—N3—C16—C15	179.9 (3)
N4—Co1—N5—C8	−1.89 (18)	N1—C11—C16—N3	−0.2 (3)
N2—Co1—N5—C8	90.38 (19)	C12—C11—C16—N3	−179.1 (3)
Cl1—Co1—N5—C8	−90.9 (2)	N1—C11—C16—C15	179.8 (2)
C7—N4—C1—C2	−179.5 (3)	C12—C11—C16—C15	0.9 (4)
Co1—N4—C1—C2	3.8 (5)	C14—C15—C16—N3	179.8 (3)
C7—N4—C1—C6	−0.7 (3)	C14—C15—C16—C11	−0.2 (4)
Co1—N4—C1—C6	−177.4 (2)	C11—N1—C17—N3	−0.4 (3)
N4—C1—C2—C3	178.7 (3)	Co1—N1—C17—N3	−172.59 (17)
C6—C1—C2—C3	0.0 (4)	C11—N1—C17—C18	−177.6 (2)
C1—C2—C3—C4	0.1 (5)	Co1—N1—C17—C18	10.2 (3)
C2—C3—C4—C5	0.0 (5)	C16—N3—C17—N1	0.3 (3)
C3—C4—C5—C6	−0.1 (5)	C16—N3—C17—C18	177.3 (3)
C7—N6—C6—C5	179.0 (3)	C20—N2—C18—C19	0.0 (3)
C7—N6—C6—C1	−1.5 (3)	Co1—N2—C18—C19	−179.8 (2)
C4—C5—C6—N6	179.6 (3)	C20—N2—C18—C17	178.4 (2)
C4—C5—C6—C1	0.2 (4)	Co1—N2—C18—C17	−1.4 (3)
N4—C1—C6—N6	1.4 (3)	N1—C17—C18—C19	172.7 (3)
C2—C1—C6—N6	−179.7 (3)	N3—C17—C18—C19	−4.0 (5)
N4—C1—C6—C5	−179.1 (2)	N1—C17—C18—N2	−5.4 (4)
C2—C1—C6—C5	−0.1 (4)	N3—C17—C18—N2	177.9 (2)
C1—N4—C7—N6	−0.3 (3)	N2—C18—C19—S2	0.6 (3)
Co1—N4—C7—N6	177.35 (18)	C17—C18—C19—S2	−177.5 (2)
C1—N4—C7—C8	−179.9 (2)	C20—S2—C19—C18	−0.7 (2)
Co1—N4—C7—C8	−2.3 (3)	C18—N2—C20—S2	−0.6 (3)
C6—N6—C7—N4	1.2 (3)	Co1—N2—C20—S2	179.15 (17)
C6—N6—C7—C8	−179.2 (3)	C19—S2—C20—N2	0.8 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O2ⁱ	0.86	1.90	2.748 (3)	169
N6—H6···O1	0.86	1.86	2.704 (3)	168
O1—H1B···Cl2ⁱⁱ	0.85	2.27	3.104 (3)	169
O1—H1A···Cl1ⁱⁱⁱ	0.85	2.43	3.272 (3)	169
O2—H2B···Cl1	0.85	2.45	3.296 (3)	171
O2—H2A···Cl2	0.85	2.21	3.052 (2)	174

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

Experimental details

Crystal data
Chemical formula	[CoCl(C₁₀H₇N₃S)₂]Cl·2H₂O
M_r	568.35
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	14.803 (4), 11.709 (3), 14.082 (4)
β (°)	101.439 (4)
V (Å³)	2392.3 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.15
Crystal size (mm)	0.20 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART 1000 CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.803, 0.803
No. of measured, independent and observed [I > 2σ(I)] reflections	12683, 4200, 3517
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.096, 1.05
No. of reflections	4200
No. of parameters	298
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.52, −0.37

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
N3—H3···O2ⁱ	0.86	1.90	2.748 (3)	169
N6—H6···O1	0.86	1.86	2.704 (3)	168
O1—H1B···Cl2ⁱⁱ	0.85	2.27	3.104 (3)	169
O1—H1A···Cl1ⁱⁱⁱ	0.85	2.43	3.272 (3)	169
O2—H2B···Cl1	0.85	2.45	3.296 (3)	171
O2—H2A···Cl2	0.85	2.21	3.052 (2)	174

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

Acknowledgements

This work was supported by the Innovation Project of Guangxi University for Nationalities (grant No. gxun-chx2011092).

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