Bis[(1-methyl-1H-benzimidazol-2-yl)methanol-κ2N3,O]bis­(thio­cyanato-κN)cobalt(II) methanol solvate

Zhou, Y.-L.; Liang, H.; Zeng, M.-H.

doi:10.1107/S1600536810002114

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 2| February 2010| Page m189

https://doi.org/10.1107/S1600536810002114

Open

access

Bis[(1-methyl-1H-benzimidazol-2-yl)methanol-κ²N³,O]bis(thiocyanato-κN)cobalt(II) methanol solvate

Yan-Ling Zhou,^a Hong Liang ^b and Ming-Hua Zeng ^b ^*

^aSchool of Chemistry and Chemical Engineering, Central South University, Changsha 410083, People's Republic of China, and ^bSchool of Chemistry and Chemical Engineering, Guangxi Normal University, Guilin 541004, People's Republic of China
^*Correspondence e-mail: zmh@mailbox.gxnu.edu.cn

(Received 13 January 2010; accepted 18 January 2010; online 23 January 2010)

In the mononuclear title complex, [Co(NCS)₂(C₉H₁₀N₂O)₂]·CH₃OH, the cobalt(II) ion is surrounded by two (1-methyl-1H-benzimidazol-2-yl)methanol bidentate ligands and two thiocyanate ligands, and exhibits a distorted octahedral coordination by four N atoms and two O atoms. The structure is consolidated by hydrogen bonds between the organic ligand, thiocyanate anion and the uncoordinated methanol molecule, leading to a chain along [100].

Related literature

For the synthesis of the ligand, see: van Albada et al. (1995 ) and literature cited therein. For the cobalt(II) dithiocyanato adduct, see: Zeng et al. (2006 ). For the zinc(II) complex of a similar N-heterocycle, see: Zhou et al. (2007 ).

Experimental

Crystal data

[Co(NCS)₂(C₉H₁₀N₂O)₂]·CH₄O
M_r = 531.53
Triclinic, $[P \overline 1]$
a = 7.5008 (13) Å
b = 10.3470 (18) Å
c = 16.042 (3) Å
α = 95.579 (3)°
β = 103.388 (3)°
γ = 95.179 (3)°
V = 1197.3 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.93 mm⁻¹
T = 173 K
0.40 × 0.36 × 0.09 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.708, T_max = 0.921
8542 measured reflections
4146 independent reflections
3288 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.116
S = 1.01
4146 reflections
298 parameters
H-atom parameters constrained
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Selected bond lengths (Å)

Co1—N6	2.035 (3)
Co1—N5	2.047 (3)
Co1—N1	2.065 (3)
Co1—N3	2.079 (3)
Co1—O1	2.284 (2)
Co1—O2	2.327 (2)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯O3	0.85	1.89	2.689 (3)	155
O3—H3A⋯S2ⁱ	0.85	2.45	3.297 (3)	179
O1—H1⋯S1ⁱ	0.85	2.36	3.177 (2)	162
Symmetry code: (i) x-1, y, z.

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ) and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810002114/si2239sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810002114/si2239Isup2.hkl

checkCIF report

Comment top

The benzimidazol alcohols have widely been used as versatile ligands in coordination chemistry, and their metal complexes are of great interest in many fields. Recently, we have reported a few benzimidazol-2-yl methanol base cobalt and zinc complexes (Zeng et al. 2006, Zhou et al. 2007). In this paper, the title new cobalt(II) complex, (Fig. 1), is reported.

The complex consists of a mononuclear cobalt(II) complex molecule and a methanol molecule. The cobalt(II) ion is surrounded by two [(1-methyl-1H-benzimidazol-2-yl)methanol bidentate ligands and two thiocyanato ligands, and exhibits a distorted octahedral coordination by four N atoms and two O atoms (Albada et al. 1995) The coordinate bond lengths (Table 1) are typical and comparable to the corresponding values observed in our previously reported similar 2-Hydroxymethylbenzimidazole cobalt(II) complex (Zeng et al. 2006).

The structure is consolidated by hydrogen bonds between the organic ligand, thiocyanate anion and the uncoordinated methanol molecule, leading to a one-dimensional chain along the [100] direction. (Table 2, Fig. 2).

Related literature top

For the synthesis of the ligand, see: van Albada et al. (1995) and literature cited therein. For the cobalt(II) dithiocyanato adduct, see: Zeng et al. (2006). For the zinc(II) complex of a similar N-heterocycle, see: Zhou et al. (2007).

Experimental top

(1-methyl-1H-benzimidazol-2-yl) methanol was purchased from a chemical supplier. This reagent (0.16 g, 1 mmol), cobalt(II) nitrate hexahydrate (0.15 g, 0.5 mmol) and ammonium thiocyanate(0.08 g, 1 mmol) were dissolved in water (10 ml) that was kept at about 333 K. Red platelets separated from the solution after two weeks.

Structure description top

For the synthesis of the ligand, see: van Albada et al. (1995) and literature cited therein. For the cobalt(II) dithiocyanato adduct, see: Zeng et al. (2006). For the zinc(II) complex of a similar N-heterocycle, see: Zhou et al. (2007).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010) and PLATON (Spek, 2009).

Figures top

	Fig. 1. Anisotropic displacement ellipsoid plot of the [Co(II)(NCS)₂(C₉H₁₀N₂O)₂] molecule at the 50% probability level; hydrogen atoms are drawn as sphere of arbitrary radius.
	Fig. 2. Part of the hydrogen bonded chains along [100] direction. Hydrogen bonds are shown as dashed lines. Symmetry codes: (i) -1 + x, y, z.

Bis[(1-methyl-1H-benzimidazol-2-yl)methanol- κ²N³,O]bis(thiocyanato-κN)cobalt(II) methanol solvate top

Crystal data top

[Co(NCS)₂(C₉H₁₀N₂O)₂]·CH₄O	Z = 2
M_r = 531.53	F(000) = 550
Triclinic, P1	D_x = 1.474 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.5008 (13) Å	Cell parameters from 4367 reflections
b = 10.3470 (18) Å	θ = 2.8–25.0°
c = 16.042 (3) Å	µ = 0.93 mm⁻¹
α = 95.579 (3)°	T = 173 K
β = 103.388 (3)°	Plate, red
γ = 95.179 (3)°	0.40 × 0.36 × 0.09 mm
V = 1197.3 (4) Å³

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	4146 independent reflections
Radiation source: fine-focus sealed tube	3288 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
phi and ω scans	θ_max = 25.0°, θ_min = 1.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
T_min = 0.708, T_max = 0.921	k = −12→12
8542 measured reflections	l = −19→19

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.116	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0643P)² + 1.1088P] where P = (F_o² + 2F_c²)/3
4146 reflections	(Δ/σ)_max = 0.001
298 parameters	Δρ_max = 0.39 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

[Co(NCS)₂(C₉H₁₀N₂O)₂]·CH₄O	γ = 95.179 (3)°
M_r = 531.53	V = 1197.3 (4) Å³
Triclinic, P1	Z = 2
a = 7.5008 (13) Å	Mo Kα radiation
b = 10.3470 (18) Å	µ = 0.93 mm⁻¹
c = 16.042 (3) Å	T = 173 K
α = 95.579 (3)°	0.40 × 0.36 × 0.09 mm
β = 103.388 (3)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	4146 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3288 reflections with I > 2σ(I)
T_min = 0.708, T_max = 0.921	R_int = 0.021
8542 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.116	H-atom parameters constrained
S = 1.01	Δρ_max = 0.39 e Å⁻³
4146 reflections	Δρ_min = −0.26 e Å⁻³
298 parameters

Special details top

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. In Checkcif report, the following ALERTS were generated

PLAT230_ALERT_2_C Hirshfeld Test Diff for S1–C19.. 6.12 su PLAT230_ALERT_2_C Hirshfeld Test Diff for S2–C20.. 5.57 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M—X) Co1–O1..5.19 su Author response: referring to the alert levels C, similar anisotropic displacement ellipsoids were observed in the solvent-free cobalt(II) complex (Zeng et al., 2006), and similar distances for S—C and Co—O (2.268 (2) Å) are found in Zeng et al. (2006).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Co1	0.49422 (6)	0.79547 (4)	0.71477 (3)	0.03196 (15)
O1	0.3407 (3)	0.9076 (2)	0.61010 (13)	0.0388 (5)
H1	0.2553	0.9321	0.6326	0.058*
O2	0.2200 (3)	0.7225 (2)	0.74875 (14)	0.0420 (6)
H2A	0.2062	0.6429	0.7575	0.063*
O3	0.0999 (4)	0.4972 (2)	0.79928 (16)	0.0552 (7)
H3A	0.0496	0.5315	0.8370	0.083*
N1	0.3872 (3)	0.6541 (3)	0.61074 (16)	0.0321 (6)
N2	0.2271 (4)	0.5910 (3)	0.47582 (16)	0.0360 (6)
N3	0.4426 (3)	0.9434 (3)	0.80037 (16)	0.0335 (6)
N4	0.3048 (4)	1.0150 (3)	0.90172 (17)	0.0377 (6)
N5	0.7251 (4)	0.8800 (3)	0.68486 (17)	0.0402 (7)
N6	0.6311 (4)	0.6910 (3)	0.80523 (19)	0.0451 (7)
C1	0.2850 (5)	0.8331 (3)	0.5273 (2)	0.0435 (8)
H1A	0.3651	0.8629	0.4901	0.052*
H1B	0.1561	0.8449	0.4996	0.052*
C2	0.2998 (4)	0.6920 (3)	0.53789 (19)	0.0335 (7)
C3	0.3678 (4)	0.5184 (3)	0.59742 (19)	0.0321 (7)
C4	0.4280 (4)	0.4266 (3)	0.6519 (2)	0.0365 (7)
H4A	0.4974	0.4526	0.7096	0.044*
C5	0.3834 (5)	0.2958 (3)	0.6193 (2)	0.0447 (8)
H5A	0.4227	0.2310	0.6554	0.054*
C6	0.2822 (5)	0.2573 (4)	0.5348 (2)	0.0479 (9)
H6B	0.2539	0.1666	0.5148	0.057*
C7	0.2218 (5)	0.3459 (4)	0.4795 (2)	0.0430 (8)
H7A	0.1532	0.3190	0.4218	0.052*
C8	0.2661 (4)	0.4773 (3)	0.51224 (19)	0.0335 (7)
C9	0.1212 (5)	0.5970 (4)	0.3872 (2)	0.0444 (8)
H9A	0.1124	0.6885	0.3776	0.067*
H9B	−0.0029	0.5510	0.3786	0.067*
H9C	0.1837	0.5554	0.3462	0.067*
C10	0.1814 (5)	0.7973 (3)	0.8195 (2)	0.0412 (8)
H10A	0.1972	0.7475	0.8698	0.049*
H10B	0.0525	0.8184	0.8045	0.049*
C11	0.3106 (4)	0.9185 (3)	0.8402 (2)	0.0348 (7)
C12	0.5277 (4)	1.0679 (3)	0.83793 (19)	0.0332 (7)
C13	0.6722 (4)	1.1464 (4)	0.8213 (2)	0.0427 (8)
H13A	0.7323	1.1183	0.7779	0.051*
C14	0.7252 (5)	1.2669 (4)	0.8701 (2)	0.0508 (9)
H14A	0.8219	1.3231	0.8589	0.061*
C15	0.6418 (5)	1.3092 (4)	0.9354 (2)	0.0506 (9)
H15A	0.6843	1.3923	0.9681	0.061*
C16	0.4986 (5)	1.2322 (4)	0.9530 (2)	0.0471 (9)
H16A	0.4411	1.2597	0.9975	0.056*
C17	0.4430 (4)	1.1128 (3)	0.9026 (2)	0.0373 (7)
C18	0.1719 (5)	1.0184 (4)	0.9551 (2)	0.0528 (10)
H18A	0.0893	0.9362	0.9418	0.079*
H18B	0.0995	1.0916	0.9433	0.079*
H18C	0.2377	1.0295	1.0162	0.079*
C19	0.8474 (4)	0.9482 (3)	0.6751 (2)	0.0354 (7)
C20	0.7421 (4)	0.6650 (3)	0.8619 (2)	0.0317 (7)
C21	0.2200 (7)	0.4131 (5)	0.8363 (3)	0.0730 (14)
H21B	0.3474	0.4535	0.8455	0.109*
H21A	0.2018	0.3309	0.7978	0.109*
H21C	0.1958	0.3952	0.8918	0.109*
S2	0.89902 (12)	0.63097 (9)	0.94306 (5)	0.0424 (2)
S1	1.01807 (12)	1.04930 (9)	0.66347 (6)	0.0445 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co1	0.0292 (2)	0.0377 (3)	0.0279 (2)	0.00460 (18)	0.00559 (17)	0.00169 (18)
O1	0.0360 (12)	0.0467 (13)	0.0333 (12)	0.0101 (10)	0.0075 (10)	0.0003 (10)
O2	0.0414 (13)	0.0489 (14)	0.0382 (13)	−0.0009 (11)	0.0173 (11)	0.0048 (11)
O3	0.0719 (18)	0.0496 (15)	0.0489 (15)	0.0112 (14)	0.0232 (14)	0.0048 (12)
N1	0.0266 (13)	0.0411 (15)	0.0290 (14)	0.0046 (11)	0.0079 (11)	0.0026 (11)
N2	0.0301 (14)	0.0506 (17)	0.0254 (13)	0.0021 (12)	0.0057 (11)	0.0000 (12)
N3	0.0262 (13)	0.0445 (16)	0.0302 (14)	0.0046 (11)	0.0069 (11)	0.0061 (12)
N4	0.0382 (15)	0.0475 (17)	0.0349 (14)	0.0134 (13)	0.0195 (12)	0.0084 (12)
N5	0.0329 (15)	0.0484 (17)	0.0403 (16)	0.0052 (13)	0.0139 (13)	−0.0018 (13)
N6	0.0438 (17)	0.0477 (18)	0.0396 (16)	0.0114 (14)	−0.0007 (14)	0.0050 (13)
C1	0.044 (2)	0.051 (2)	0.0332 (18)	0.0089 (16)	0.0055 (15)	0.0054 (15)
C2	0.0247 (15)	0.0475 (19)	0.0302 (16)	0.0046 (13)	0.0107 (13)	0.0036 (14)
C3	0.0243 (15)	0.0425 (18)	0.0324 (16)	0.0016 (13)	0.0149 (13)	0.0009 (14)
C4	0.0317 (17)	0.0443 (19)	0.0358 (17)	0.0025 (14)	0.0135 (14)	0.0045 (15)
C5	0.045 (2)	0.043 (2)	0.052 (2)	0.0053 (16)	0.0233 (17)	0.0076 (17)
C6	0.051 (2)	0.040 (2)	0.055 (2)	0.0002 (17)	0.0227 (18)	−0.0050 (17)
C7	0.0381 (19)	0.056 (2)	0.0343 (18)	−0.0029 (16)	0.0159 (15)	−0.0067 (16)
C8	0.0266 (16)	0.0448 (19)	0.0313 (16)	0.0016 (14)	0.0145 (13)	−0.0001 (14)
C9	0.0383 (19)	0.062 (2)	0.0281 (17)	0.0057 (17)	0.0020 (14)	−0.0007 (16)
C10	0.0424 (19)	0.045 (2)	0.0438 (19)	0.0089 (15)	0.0213 (16)	0.0116 (15)
C11	0.0297 (16)	0.0445 (19)	0.0340 (17)	0.0094 (14)	0.0107 (14)	0.0120 (14)
C12	0.0272 (16)	0.0422 (18)	0.0291 (16)	0.0095 (14)	0.0029 (13)	0.0037 (14)
C13	0.0296 (17)	0.053 (2)	0.0430 (19)	0.0019 (15)	0.0110 (15)	−0.0069 (16)
C14	0.0345 (19)	0.058 (2)	0.056 (2)	−0.0017 (17)	0.0112 (17)	−0.0066 (19)
C15	0.041 (2)	0.053 (2)	0.051 (2)	0.0014 (17)	0.0065 (17)	−0.0123 (18)
C16	0.046 (2)	0.059 (2)	0.0378 (19)	0.0163 (18)	0.0111 (16)	−0.0029 (17)
C17	0.0311 (17)	0.050 (2)	0.0332 (17)	0.0120 (15)	0.0091 (14)	0.0066 (15)
C18	0.057 (2)	0.061 (2)	0.054 (2)	0.0158 (19)	0.037 (2)	0.0099 (19)
C19	0.0328 (18)	0.0428 (19)	0.0317 (17)	0.0155 (15)	0.0079 (14)	0.0006 (14)
C20	0.0321 (17)	0.0296 (16)	0.0367 (17)	0.0036 (13)	0.0146 (15)	0.0040 (13)
C21	0.084 (3)	0.101 (4)	0.056 (3)	0.047 (3)	0.039 (2)	0.032 (3)
S2	0.0376 (5)	0.0594 (6)	0.0333 (4)	0.0147 (4)	0.0086 (4)	0.0129 (4)
S1	0.0376 (5)	0.0423 (5)	0.0599 (6)	0.0092 (4)	0.0199 (4)	0.0134 (4)

Geometric parameters (Å, º) top

Co1—N6	2.035 (3)	C5—C6	1.392 (5)
Co1—N5	2.047 (3)	C5—H5A	0.9500
Co1—N1	2.065 (3)	C6—C7	1.371 (5)
Co1—N3	2.079 (3)	C6—H6B	0.9500
Co1—O1	2.284 (2)	C7—C8	1.390 (5)
Co1—O2	2.327 (2)	C7—H7A	0.9500
O1—C1	1.421 (4)	C9—H9A	0.9800
O1—H1	0.8500	C9—H9B	0.9800
O2—C10	1.411 (4)	C9—H9C	0.9800
O2—H2A	0.8500	C10—C11	1.474 (5)
O3—C21	1.384 (5)	C10—H10A	0.9900
O3—H3A	0.8501	C10—H10B	0.9900
N1—C2	1.315 (4)	C12—C13	1.387 (5)
N1—C3	1.389 (4)	C12—C17	1.401 (4)
N2—C2	1.351 (4)	C13—C14	1.380 (5)
N2—C8	1.388 (4)	C13—H13A	0.9500
N2—C9	1.470 (4)	C14—C15	1.392 (5)
N3—C11	1.317 (4)	C14—H14A	0.9500
N3—C12	1.397 (4)	C15—C16	1.378 (5)
N4—C11	1.345 (4)	C15—H15A	0.9500
N4—C17	1.378 (4)	C16—C17	1.382 (5)
N4—C18	1.457 (4)	C16—H16A	0.9500
N5—C19	1.155 (4)	C18—H18A	0.9800
N6—C20	1.154 (4)	C18—H18B	0.9800
C1—C2	1.498 (5)	C18—H18C	0.9800
C1—H1A	0.9900	C19—S1	1.636 (4)
C1—H1B	0.9900	C20—S2	1.630 (3)
C3—C4	1.388 (5)	C21—H21B	0.9800
C3—C8	1.405 (4)	C21—H21A	0.9800
C4—C5	1.384 (5)	C21—H21C	0.9800
C4—H4A	0.9500

N6—Co1—N5	95.76 (12)	C7—C6—H6B	118.9
N6—Co1—N1	102.52 (11)	C5—C6—H6B	118.9
N5—Co1—N1	102.62 (10)	C6—C7—C8	116.5 (3)
N6—Co1—N3	96.87 (11)	C6—C7—H7A	121.7
N5—Co1—N3	101.37 (10)	C8—C7—H7A	121.7
N1—Co1—N3	147.26 (10)	N2—C8—C7	132.0 (3)
N6—Co1—O1	178.26 (10)	N2—C8—C3	105.7 (3)
N5—Co1—O1	84.12 (10)	C7—C8—C3	122.2 (3)
N1—Co1—O1	75.83 (9)	N2—C9—H9A	109.5
N3—Co1—O1	84.85 (9)	N2—C9—H9B	109.5
N6—Co1—O2	88.91 (11)	H9A—C9—H9B	109.5
N5—Co1—O2	173.52 (10)	N2—C9—H9C	109.5
N1—Co1—O2	80.65 (9)	H9A—C9—H9C	109.5
N3—Co1—O2	73.54 (9)	H9B—C9—H9C	109.5
O1—Co1—O2	91.34 (8)	O2—C10—C11	107.8 (3)
C1—O1—Co1	113.38 (19)	O2—C10—H10A	110.1
C1—O1—H1	116.7	C11—C10—H10A	110.1
Co1—O1—H1	100.9	O2—C10—H10B	110.1
C10—O2—Co1	114.71 (19)	C11—C10—H10B	110.1
C10—O2—H2A	106.8	H10A—C10—H10B	108.5
Co1—O2—H2A	116.5	N3—C11—N4	113.3 (3)
C21—O3—H3A	109.5	N3—C11—C10	123.5 (3)
C2—N1—C3	106.1 (3)	N4—C11—C10	123.2 (3)
C2—N1—Co1	117.9 (2)	C13—C12—N3	131.3 (3)
C3—N1—Co1	135.7 (2)	C13—C12—C17	119.5 (3)
C2—N2—C8	106.9 (3)	N3—C12—C17	109.2 (3)
C2—N2—C9	127.6 (3)	C14—C13—C12	117.4 (3)
C8—N2—C9	125.5 (3)	C14—C13—H13A	121.3
C11—N3—C12	104.8 (3)	C12—C13—H13A	121.3
C11—N3—Co1	118.5 (2)	C13—C14—C15	122.4 (4)
C12—N3—Co1	136.2 (2)	C13—C14—H14A	118.8
C11—N4—C17	107.4 (3)	C15—C14—H14A	118.8
C11—N4—C18	126.4 (3)	C16—C15—C14	121.0 (3)
C17—N4—C18	126.2 (3)	C16—C15—H15A	119.5
C19—N5—Co1	167.6 (3)	C14—C15—H15A	119.5
C20—N6—Co1	160.2 (3)	C15—C16—C17	116.6 (3)
O1—C1—C2	108.7 (3)	C15—C16—H16A	121.7
O1—C1—H1A	110.0	C17—C16—H16A	121.7
C2—C1—H1A	110.0	N4—C17—C16	131.6 (3)
O1—C1—H1B	110.0	N4—C17—C12	105.3 (3)
C2—C1—H1B	110.0	C16—C17—C12	123.2 (3)
H1A—C1—H1B	108.3	N4—C18—H18A	109.5
N1—C2—N2	112.9 (3)	N4—C18—H18B	109.5
N1—C2—C1	122.2 (3)	H18A—C18—H18B	109.5
N2—C2—C1	124.9 (3)	N4—C18—H18C	109.5
C4—C3—N1	131.5 (3)	H18A—C18—H18C	109.5
C4—C3—C8	120.0 (3)	H18B—C18—H18C	109.5
N1—C3—C8	108.5 (3)	N5—C19—S1	177.8 (3)
C5—C4—C3	117.7 (3)	N6—C20—S2	178.9 (3)
C5—C4—H4A	121.2	O3—C21—H21B	109.5
C3—C4—H4A	121.2	O3—C21—H21A	109.5
C4—C5—C6	121.3 (3)	H21B—C21—H21A	109.5
C4—C5—H5A	119.3	O3—C21—H21C	109.5
C6—C5—H5A	119.3	H21B—C21—H21C	109.5
C7—C6—C5	122.2 (3)	H21A—C21—H21C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O3	0.85	1.89	2.689 (3)	155
O3—H3A···S2ⁱ	0.85	2.45	3.297 (3)	179
O1—H1···S1ⁱ	0.85	2.36	3.177 (2)	162

Symmetry code: (i) x−1, y, z.

Experimental details

Crystal data
Chemical formula	[Co(NCS)₂(C₉H₁₀N₂O)₂]·CH₄O
M_r	531.53
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	7.5008 (13), 10.3470 (18), 16.042 (3)
α, β, γ (°)	95.579 (3), 103.388 (3), 95.179 (3)
V (Å³)	1197.3 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.93
Crystal size (mm)	0.40 × 0.36 × 0.09

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.708, 0.921
No. of measured, independent and observed [I > 2σ(I)] reflections	8542, 4146, 3288
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.116, 1.01
No. of reflections	4146
No. of parameters	298
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.26

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010) and PLATON (Spek, 2009).

Selected bond lengths (Å) top

Co1—N6	2.035 (3)	Co1—N3	2.079 (3)
Co1—N5	2.047 (3)	Co1—O1	2.284 (2)
Co1—N1	2.065 (3)	Co1—O2	2.327 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O3	0.85	1.89	2.689 (3)	155.2
O3—H3A···S2ⁱ	0.85	2.45	3.297 (3)	178.8
O1—H1···S1ⁱ	0.85	2.36	3.177 (2)	161.7

Symmetry code: (i) x−1, y, z.

Acknowledgements

We thank Central South University and Guangxi Normal University for supporting this study.

References

Albada, G. A. van, Lakin, M. T., Veldman, N., Spek, A. L. & Reedijk, J. (1995). Inorg. Chem. 34, 4910–4917. CSD CrossRef Web of Science Google Scholar
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2001). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Goöttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). publCIF. In preparation. Google Scholar
Zeng, M.-H., Zhou, Y.-L. & Ng, S. W. (2006). Acta Cryst. E62, m2101–m2102. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zhou, Y.-L., Zeng, M.-H. & Ng, S. W. (2007). Acta Cryst. E63, m15–m16. Web of Science CSD CrossRef IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.