(2-Acetyl­phenolato)(2-{1-[2-(morpholin-4-yl)ethyl­imino]­eth­yl}phenolato)(thio­cyanato-κN)­cobalt(III)

Wang, C.-Y.

doi:10.1107/S1600536811025116

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page m1008

doi:10.1107/S1600536811025116

Open

access

(2-Acetylphenolato)(2-{1-[2-(morpholin-4-yl)ethylimino]ethyl}phenolato)(thiocyanato-κN)cobalt(III)

Chen-Yi Wang ^a ^*

^aDepartment of Chemistry, Huzhou University, Huzhou 313000, People's Republic of China
^*Correspondence e-mail: chenyi_wang@163.com

(Received 23 June 2011; accepted 26 June 2011; online 30 June 2011)

The title mononuclear cobalt(III) complex, [Co(C₁₄H₁₉N₂O₂)(C₈H₇O₂)(NCS)], was obtained by the reaction of 2-acetylphenol, 2-(morpholin-4-yl)ethylamine, ammonium thiocyanate and cobalt nitrate in methanol. The Co^III atom is coordinated by one phenolate O, one imine N, and one amine N atom of the tridentate Schiff base ligand, two O atoms of the 2-acetylphenolate anion and one thiocyanate N atom. This results in a fairly regular fac-CoN₃O₃ octahedral coordination geometry for the metal ion. The dihedral angle between the two benzene rings is 88.3 (3)°.

Related literature

For background to urease inhibitors, see: Wang (2009 ); Wang & Ye (2011 ). For similar cobalt(III) complexes, see: Li et al. (2007 , 2008 ); Liu (2010 ); Wu et al. (2011 ).

Experimental

Crystal data

[Co(C₁₄H₁₉N₂O₂)(C₈H₇O₂)(NCS)]
M_r = 499.46
Monoclinic, P 2₁ /c
a = 8.145 (2) Å
b = 15.801 (2) Å
c = 17.702 (3) Å
β = 102.687 (3)°
V = 2222.6 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.90 mm⁻¹
T = 298 K
0.32 × 0.30 × 0.28 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.761, T_max = 0.786
13159 measured reflections
4588 independent reflections
2764 reflections with I > 2σ(I)
R_int = 0.047

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.101
S = 1.03
4588 reflections
291 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Selected bond lengths (Å)

Co1—O1	1.9094 (19)
Co1—O2	1.8621 (18)
Co1—O3	1.8624 (19)
Co1—N1	1.894 (2)
Co1—N3	1.914 (3)
Co1—N2	2.054 (2)

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811025116/hb5932sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811025116/hb5932Isup2.hkl

checkCIF report

Comment top

As part of our investigations into urease inhibitors (Wang & Ye, 2011; Wang, 2009), we have synthesized the title compound, a new mononuclear cobalt(III) complex, Fig. 1. The Co atom in the complex is six-coordinated by one phenolate O, one imine N, and one amine N atoms of a Schiff base ligand 2-[1-(2-morpholin-4-ylethylimino)ethyl]phenolate, two O atoms of 2-acetylphenolate, and one thiocyanate N atom, forming an octahedral geometry. The dihedral angle between the two benzene rings are 88.3 (3) °. The three trans angles at Co atom are in the range 175.1 (1)–177.5 (1)°; the other angles are close to 90°, ranging from 84.4 (1) to 94.2 (1)° (Table 1), indicating a slightly distorted octahedral coordination. The Co–O and Co–N bond lengths (Table 1) are typical and are comparable with those observed in other similar cobalt(III) complexes (Li et al., 2007; Liu, 2010; Li et al., 2008; Wu et al., 2011).

Related literature top

For background to urease inhibitors, see: Wang (2009); Wang & Ye (2011). For similar cobalt(III) complexes, see: Li et al. (2007, 2008); Liu (2010); Wu et al. (2011).

Experimental top

2-Acetylphenol (1.0 mmol, 0.136 g), 2-morpholin-4-ylethylamine (0.5 mmol, 0.065 g), ammonium thiocyanate (1.0 mmol, 0.076 g), and cobalt nitrate hexahydrate (0.5 mmol, 0.145 g) were dissolved in MeOH (30 ml). The mixture was stirred at room temperature for 10 min to give a clear deep brown solution. After keeping the solution in air for a week, brown block-shaped crystals were formed at the bottom of the vessel.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); 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, showing displacement ellipsoids drawn at the 30% probability level.

(2-Acetylphenolato)(2-{1-[2-(morpholin-4- yl)ethylimino]ethyl}phenolato)(thiocyanato-κN)cobalt(III) top

Crystal data top

[Co(C₁₄H₁₉N₂O₂)(C₈H₇O₂)(NCS)]	F(000) = 1040
M_r = 499.46	D_x = 1.493 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.145 (2) Å	Cell parameters from 2215 reflections
b = 15.801 (2) Å	θ = 2.5–24.5°
c = 17.702 (3) Å	µ = 0.90 mm⁻¹
β = 102.687 (3)°	T = 298 K
V = 2222.6 (7) Å³	Block, brown
Z = 4	0.32 × 0.30 × 0.28 mm

Data collection top

Bruker SMART CCD diffractometer	4588 independent reflections
Radiation source: fine-focus sealed tube	2764 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.047
ω scans	θ_max = 26.5°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→9
T_min = 0.761, T_max = 0.786	k = −15→19
13159 measured reflections	l = −21→22

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.101	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0387P)² + 0.1364P] where P = (F_o² + 2F_c²)/3
4588 reflections	(Δ/σ)_max < 0.001
291 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

[Co(C₁₄H₁₉N₂O₂)(C₈H₇O₂)(NCS)]	V = 2222.6 (7) Å³
M_r = 499.46	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.145 (2) Å	µ = 0.90 mm⁻¹
b = 15.801 (2) Å	T = 298 K
c = 17.702 (3) Å	0.32 × 0.30 × 0.28 mm
β = 102.687 (3)°

Data collection top

Bruker SMART CCD diffractometer	4588 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2764 reflections with I > 2σ(I)
T_min = 0.761, T_max = 0.786	R_int = 0.047
13159 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.101	H-atom parameters constrained
S = 1.03	Δρ_max = 0.24 e Å⁻³
4588 reflections	Δρ_min = −0.22 e Å⁻³
291 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	0.10480 (5)	0.75033 (2)	0.40903 (2)	0.04240 (14)
N1	0.2071 (3)	0.84863 (14)	0.45991 (14)	0.0451 (6)
N2	0.2519 (3)	0.76544 (13)	0.32944 (13)	0.0423 (6)
N3	−0.0691 (3)	0.81713 (16)	0.34625 (15)	0.0553 (7)
O1	0.0119 (2)	0.64890 (12)	0.35843 (11)	0.0511 (5)
O2	0.2783 (2)	0.69333 (11)	0.47566 (10)	0.0445 (5)
O3	−0.0305 (2)	0.73184 (12)	0.47967 (12)	0.0545 (6)
O4	0.3888 (3)	0.69744 (15)	0.20174 (14)	0.0762 (7)
S1	−0.30242 (11)	0.92290 (6)	0.25423 (5)	0.0708 (3)
C1	0.1654 (3)	0.55174 (17)	0.45072 (16)	0.0406 (7)
C2	0.1808 (4)	0.46685 (18)	0.47754 (18)	0.0481 (7)
H2	0.1094	0.4261	0.4501	0.058*
C3	0.2958 (4)	0.44293 (19)	0.54166 (18)	0.0542 (8)
H3	0.3012	0.3870	0.5585	0.065*
C4	0.4056 (4)	0.5034 (2)	0.58189 (17)	0.0510 (8)
H4	0.4868	0.4873	0.6251	0.061*
C5	0.3955 (3)	0.58572 (18)	0.55864 (16)	0.0432 (7)
H5	0.4701	0.6249	0.5866	0.052*
C6	0.2756 (3)	0.61332 (18)	0.49350 (16)	0.0399 (7)
C7	0.0426 (3)	0.57306 (18)	0.38210 (17)	0.0429 (7)
C8	−0.0548 (4)	0.50563 (19)	0.33162 (17)	0.0603 (9)
H8A	−0.1453	0.5311	0.2947	0.090*
H8B	−0.0997	0.4662	0.3631	0.090*
H8C	0.0185	0.4763	0.3047	0.090*
C9	−0.0742 (4)	0.79083 (19)	0.52384 (16)	0.0465 (7)
C10	−0.2153 (4)	0.7738 (2)	0.55482 (18)	0.0576 (9)
H10	−0.2744	0.7236	0.5419	0.069*
C11	−0.2673 (4)	0.8297 (2)	0.60370 (19)	0.0673 (9)
H11	−0.3606	0.8169	0.6239	0.081*
C12	−0.1830 (5)	0.9046 (2)	0.62323 (19)	0.0711 (10)
H12	−0.2208	0.9431	0.6553	0.085*
C13	−0.0427 (4)	0.9222 (2)	0.59514 (17)	0.0614 (9)
H13	0.0156	0.9722	0.6100	0.074*
C14	0.0158 (4)	0.86696 (18)	0.54447 (16)	0.0468 (7)
C15	0.1688 (4)	0.88750 (17)	0.51812 (17)	0.0473 (7)
C16	0.2859 (4)	0.95472 (19)	0.56150 (17)	0.0659 (9)
H16A	0.3996	0.9422	0.5584	0.099*
H16B	0.2779	0.9553	0.6148	0.099*
H16C	0.2544	1.0091	0.5388	0.099*
C17	0.3581 (4)	0.86927 (19)	0.43098 (18)	0.0557 (8)
H17A	0.4518	0.8344	0.4566	0.067*
H17B	0.3883	0.9282	0.4414	0.067*
C18	0.3200 (4)	0.85313 (18)	0.34579 (17)	0.0535 (8)
H18A	0.4217	0.8595	0.3263	0.064*
H18B	0.2381	0.8940	0.3196	0.064*
C19	0.1570 (4)	0.75906 (19)	0.24703 (16)	0.0548 (8)
H19A	0.0748	0.8043	0.2363	0.066*
H19B	0.0967	0.7057	0.2397	0.066*
C20	0.2705 (5)	0.7645 (2)	0.19053 (18)	0.0676 (10)
H20A	0.2031	0.7622	0.1381	0.081*
H20B	0.3298	0.8181	0.1971	0.081*
C21	0.4903 (4)	0.7038 (2)	0.2774 (2)	0.0716 (10)
H21A	0.5525	0.7566	0.2820	0.086*
H21B	0.5712	0.6578	0.2857	0.086*
C22	0.3886 (3)	0.70057 (19)	0.33915 (17)	0.0545 (8)
H22A	0.3387	0.6448	0.3388	0.065*
H22B	0.4638	0.7085	0.3893	0.065*
C23	−0.1659 (4)	0.86167 (19)	0.30900 (18)	0.0475 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co1	0.0373 (2)	0.0384 (2)	0.0506 (3)	−0.00521 (18)	0.00765 (17)	−0.00324 (19)
N1	0.0408 (14)	0.0395 (14)	0.0524 (16)	−0.0071 (11)	0.0048 (12)	−0.0005 (12)
N2	0.0401 (13)	0.0395 (15)	0.0455 (14)	−0.0035 (11)	0.0054 (11)	0.0020 (11)
N3	0.0447 (16)	0.0499 (16)	0.0682 (19)	0.0013 (13)	0.0055 (14)	−0.0069 (14)
O1	0.0479 (12)	0.0509 (14)	0.0541 (13)	−0.0085 (10)	0.0101 (10)	−0.0053 (10)
O2	0.0446 (11)	0.0380 (12)	0.0486 (12)	−0.0066 (9)	0.0053 (9)	0.0015 (10)
O3	0.0544 (13)	0.0459 (13)	0.0688 (15)	−0.0115 (10)	0.0257 (12)	−0.0131 (10)
O4	0.0883 (18)	0.0750 (18)	0.0742 (17)	−0.0075 (15)	0.0372 (15)	−0.0125 (14)
S1	0.0555 (5)	0.0781 (7)	0.0741 (6)	0.0045 (5)	0.0040 (5)	0.0192 (5)
C1	0.0392 (16)	0.0378 (17)	0.0484 (18)	−0.0029 (13)	0.0175 (14)	−0.0080 (14)
C2	0.0455 (17)	0.0415 (18)	0.061 (2)	−0.0057 (15)	0.0198 (16)	−0.0056 (16)
C3	0.061 (2)	0.0387 (18)	0.066 (2)	0.0023 (16)	0.0217 (18)	0.0027 (16)
C4	0.0480 (18)	0.053 (2)	0.0512 (19)	0.0055 (16)	0.0098 (15)	0.0027 (16)
C5	0.0437 (17)	0.0459 (18)	0.0406 (17)	−0.0035 (14)	0.0104 (14)	−0.0018 (14)
C6	0.0390 (16)	0.0432 (18)	0.0419 (18)	−0.0041 (14)	0.0187 (14)	−0.0045 (14)
C7	0.0395 (16)	0.0409 (18)	0.0525 (19)	−0.0070 (14)	0.0192 (14)	−0.0069 (15)
C8	0.061 (2)	0.056 (2)	0.063 (2)	−0.0134 (17)	0.0116 (17)	−0.0185 (17)
C9	0.0444 (17)	0.0449 (18)	0.0476 (18)	0.0045 (15)	0.0048 (14)	−0.0029 (15)
C10	0.052 (2)	0.061 (2)	0.062 (2)	−0.0026 (16)	0.0190 (17)	−0.0055 (17)
C11	0.066 (2)	0.079 (3)	0.061 (2)	0.008 (2)	0.0220 (19)	−0.003 (2)
C12	0.082 (3)	0.072 (3)	0.061 (2)	0.017 (2)	0.020 (2)	−0.014 (2)
C13	0.079 (2)	0.050 (2)	0.053 (2)	0.0022 (18)	0.0078 (19)	−0.0107 (16)
C14	0.0533 (18)	0.0416 (18)	0.0418 (18)	0.0037 (15)	0.0024 (15)	0.0011 (14)
C15	0.0552 (19)	0.0342 (16)	0.0464 (19)	0.0005 (15)	−0.0023 (16)	0.0064 (14)
C16	0.077 (2)	0.052 (2)	0.062 (2)	−0.0169 (18)	0.0025 (19)	−0.0124 (17)
C17	0.0499 (19)	0.0502 (19)	0.067 (2)	−0.0137 (15)	0.0132 (17)	−0.0100 (17)
C18	0.0531 (19)	0.0438 (19)	0.065 (2)	−0.0103 (15)	0.0165 (16)	0.0020 (16)
C19	0.0546 (19)	0.060 (2)	0.0465 (19)	−0.0074 (16)	0.0047 (15)	0.0000 (16)
C20	0.078 (2)	0.077 (3)	0.048 (2)	−0.015 (2)	0.0146 (18)	−0.0008 (18)
C21	0.060 (2)	0.074 (3)	0.088 (3)	0.006 (2)	0.033 (2)	0.010 (2)
C22	0.0481 (18)	0.052 (2)	0.068 (2)	0.0062 (16)	0.0220 (16)	0.0108 (17)
C23	0.0411 (18)	0.0464 (19)	0.057 (2)	−0.0080 (15)	0.0137 (15)	−0.0085 (16)

Geometric parameters (Å, º) top

Co1—O1	1.9094 (19)	C8—H8C	0.9600
Co1—O2	1.8621 (18)	C9—C10	1.404 (4)
Co1—O3	1.8624 (19)	C9—C14	1.414 (4)
Co1—N1	1.894 (2)	C10—C11	1.368 (4)
Co1—N3	1.914 (3)	C10—H10	0.9300
Co1—N2	2.054 (2)	C11—C12	1.374 (4)
N1—C15	1.295 (3)	C11—H11	0.9300
N1—C17	1.469 (3)	C12—C13	1.371 (4)
N2—C22	1.495 (3)	C12—H12	0.9300
N2—C19	1.497 (3)	C13—C14	1.408 (4)
N2—C18	1.497 (3)	C13—H13	0.9300
N3—C23	1.150 (3)	C14—C15	1.460 (4)
O1—C7	1.276 (3)	C15—C16	1.519 (4)
O2—C6	1.304 (3)	C16—H16A	0.9600
O3—C9	1.315 (3)	C16—H16B	0.9600
O4—C21	1.415 (4)	C16—H16C	0.9600
O4—C20	1.416 (4)	C17—C18	1.493 (4)
S1—C23	1.625 (3)	C17—H17A	0.9700
C1—C2	1.419 (4)	C17—H17B	0.9700
C1—C6	1.424 (4)	C18—H18A	0.9700
C1—C7	1.434 (4)	C18—H18B	0.9700
C2—C3	1.357 (4)	C19—C20	1.506 (4)
C2—H2	0.9300	C19—H19A	0.9700
C3—C4	1.393 (4)	C19—H19B	0.9700
C3—H3	0.9300	C20—H20A	0.9700
C4—C5	1.362 (4)	C20—H20B	0.9700
C4—H4	0.9300	C21—C22	1.510 (4)
C5—C6	1.407 (4)	C21—H21A	0.9700
C5—H5	0.9300	C21—H21B	0.9700
C7—C8	1.500 (4)	C22—H22A	0.9700
C8—H8A	0.9600	C22—H22B	0.9700
C8—H8B	0.9600

O2—Co1—O3	88.70 (8)	C11—C10—H10	119.4
O2—Co1—N1	84.38 (9)	C9—C10—H10	119.4
O3—Co1—N1	94.17 (9)	C10—C11—C12	120.6 (3)
O2—Co1—O1	93.36 (8)	C10—C11—H11	119.7
O3—Co1—O1	87.21 (8)	C12—C11—H11	119.7
N1—Co1—O1	177.31 (9)	C13—C12—C11	119.6 (3)
O2—Co1—N3	175.10 (9)	C13—C12—H12	120.2
O3—Co1—N3	90.27 (10)	C11—C12—H12	120.2
N1—Co1—N3	90.93 (10)	C12—C13—C14	122.1 (3)
O1—Co1—N3	91.38 (9)	C12—C13—H13	119.0
O2—Co1—N2	90.86 (8)	C14—C13—H13	119.0
O3—Co1—N2	177.51 (8)	C13—C14—C9	117.6 (3)
N1—Co1—N2	88.22 (9)	C13—C14—C15	119.9 (3)
O1—Co1—N2	90.37 (8)	C9—C14—C15	122.5 (3)
N3—Co1—N2	90.37 (10)	N1—C15—C14	121.4 (3)
C15—N1—C17	122.6 (2)	N1—C15—C16	120.0 (3)
C15—N1—Co1	127.5 (2)	C14—C15—C16	118.7 (3)
C17—N1—Co1	109.32 (18)	C15—C16—H16A	109.5
C22—N2—C19	106.1 (2)	C15—C16—H16B	109.5
C22—N2—C18	112.2 (2)	H16A—C16—H16B	109.5
C19—N2—C18	109.9 (2)	C15—C16—H16C	109.5
C22—N2—Co1	111.92 (16)	H16A—C16—H16C	109.5
C19—N2—Co1	114.01 (17)	H16B—C16—H16C	109.5
C18—N2—Co1	102.84 (16)	N1—C17—C18	108.0 (2)
C23—N3—Co1	175.3 (2)	N1—C17—H17A	110.1
C7—O1—Co1	127.26 (19)	C18—C17—H17A	110.1
C6—O2—Co1	124.85 (17)	N1—C17—H17B	110.1
C9—O3—Co1	124.42 (18)	C18—C17—H17B	110.1
C21—O4—C20	108.5 (3)	H17A—C17—H17B	108.4
C2—C1—C6	118.0 (3)	C17—C18—N2	109.8 (2)
C2—C1—C7	119.9 (3)	C17—C18—H18A	109.7
C6—C1—C7	122.1 (3)	N2—C18—H18A	109.7
C3—C2—C1	122.5 (3)	C17—C18—H18B	109.7
C3—C2—H2	118.8	N2—C18—H18B	109.7
C1—C2—H2	118.8	H18A—C18—H18B	108.2
C2—C3—C4	119.0 (3)	N2—C19—C20	112.5 (2)
C2—C3—H3	120.5	N2—C19—H19A	109.1
C4—C3—H3	120.5	C20—C19—H19A	109.1
C5—C4—C3	120.8 (3)	N2—C19—H19B	109.1
C5—C4—H4	119.6	C20—C19—H19B	109.1
C3—C4—H4	119.6	H19A—C19—H19B	107.8
C4—C5—C6	121.9 (3)	O4—C20—C19	111.3 (3)
C4—C5—H5	119.0	O4—C20—H20A	109.4
C6—C5—H5	119.0	C19—C20—H20A	109.4
O2—C6—C5	117.0 (3)	O4—C20—H20B	109.4
O2—C6—C1	125.2 (3)	C19—C20—H20B	109.4
C5—C6—C1	117.9 (3)	H20A—C20—H20B	108.0
O1—C7—C1	123.3 (3)	O4—C21—C22	112.6 (3)
O1—C7—C8	115.6 (3)	O4—C21—H21A	109.1
C1—C7—C8	121.1 (3)	C22—C21—H21A	109.1
C7—C8—H8A	109.5	O4—C21—H21B	109.1
C7—C8—H8B	109.5	C22—C21—H21B	109.1
H8A—C8—H8B	109.5	H21A—C21—H21B	107.8
C7—C8—H8C	109.5	N2—C22—C21	114.0 (2)
H8A—C8—H8C	109.5	N2—C22—H22A	108.8
H8B—C8—H8C	109.5	C21—C22—H22A	108.8
O3—C9—C10	116.6 (3)	N2—C22—H22B	108.8
O3—C9—C14	124.3 (3)	C21—C22—H22B	108.8
C10—C9—C14	119.0 (3)	H22A—C22—H22B	107.6
C11—C10—C9	121.1 (3)	N3—C23—S1	178.3 (3)

Experimental details

Crystal data
Chemical formula	[Co(C₁₄H₁₉N₂O₂)(C₈H₇O₂)(NCS)]
M_r	499.46
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	8.145 (2), 15.801 (2), 17.702 (3)
β (°)	102.687 (3)
V (Å³)	2222.6 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.90
Crystal size (mm)	0.32 × 0.30 × 0.28

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.761, 0.786
No. of measured, independent and observed [I > 2σ(I)] reflections	13159, 4588, 2764
R_int	0.047
(sin θ/λ)_max (Å⁻¹)	0.628

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.101, 1.03
No. of reflections	4588
No. of parameters	291
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.22

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Co1—O1	1.9094 (19)	Co1—N1	1.894 (2)
Co1—O2	1.8621 (18)	Co1—N3	1.914 (3)
Co1—O3	1.8624 (19)	Co1—N2	2.054 (2)

Acknowledgements

This work was supported financially by the Natural Science Foundation of China (No. 31071856), the Natural Science Foundation of Zhejiang Province (No. Y407318) and the Applied Research Project on Nonprofit Technology of Zhejiang Province (No. 2010 C32060).

References

Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Li, K., Huang, S.-S., Zhou, Q., Li, H. & Diao, Y.-P. (2007). Acta Cryst. E63, m2274. Web of Science CSD CrossRef IUCr Journals Google Scholar
Li, S., Wang, S.-B., Tang, K. & Ma, Y.-F. (2008). Acta Cryst. E64, m823. Web of Science CSD CrossRef IUCr Journals Google Scholar
Liu, L.-J. (2010). Acta Cryst. E66, m1143. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, C.-Y. (2009). J. Coord. Chem. 62, 2860–2868. Web of Science CSD CrossRef CAS Google Scholar
Wang, C. Y. & Ye, J. Y. (2011). Russ. J. Coord. Chem. 37, 235–241. Web of Science CrossRef CAS Google Scholar
Wu, Q.-J., Chen, X.-H., Jiang, J., Cai, B.-Q. & Xie, Y.-P. (2011). Acta Cryst. E67, m293. 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.