Bis(2-cyclo­hexyl­imino­methyl-4,6-dihydro­seleno­phenolato)cobalt(II) acetonitrile solvate

Cui, Y.-M.; Zhang, X.; Wang, L.-J.; Zeng, Q.-F.

doi:10.1107/S1600536809034795

Bis(2-cyclohexyliminomethyl-4,6-dihydroselenophenolato)cobalt(II) acetonitrile solvate

Y.-M. Cui, X. Zhang, L.-J. Wang and Q.-F. Zeng

In the title compound, [Co(C₁₃H₁₆NOSe₂)₂]·CH₃CN, the Co^II atom is four-coordinated by two N,O-bidentate Schiff base ligands, resulting in a distorted tetrahedral coordination for the metal ion.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536809034795/hb5080sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536809034795/hb5080Isup2.hkl Contains datablock I

CCDC reference: 750530

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.009 Å
R factor = 0.044
wR factor = 0.141
Data-to-parameter ratio = 16.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Co1    --  O1      ..       5.03 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Co1    --  O2      ..       5.57 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Co1    --  N1      ..       5.80 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Co1    --  N2      ..       5.60 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O1
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O2
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        Co1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C17
PLAT341_ALERT_3_C Low Bond Precision on  C-C Bonds (x 1000) Ang ..          9
PLAT420_ALERT_2_C D-H Without Acceptor       Se1    -   H1     ...          ?
PLAT420_ALERT_2_C D-H Without Acceptor       Se2    -   H2     ...          ?
PLAT420_ALERT_2_C D-H Without Acceptor       Se3    -   H3A    ...          ?
PLAT420_ALERT_2_C D-H Without Acceptor       Se4    -   H4     ...          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT153_ALERT_1_C The su's on the Cell Axes   are Equal (x 100000)         50 Ang.
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors of         C28

Alert level G
PLAT128_ALERT_4_G Non-standard setting of Space-group P21/c   ....      P21/n

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
  16 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  12 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

There has been much research interest in Schiff base metal complexes due to their molecular architectures and biological activities (Shi et al., 2007; Shi et al., 2008). In this work, we report here the crystal structure of the title compound, (I). In (I), all bond lengths are within normal ranges (Allen et al., 1987) (Fig. 1). The Co^II is four-coordinated in a distorted tetrahedral coordination by two N atoms and two O atoms of the Schiff base ligand.

Related literature top

For background to Schiff bases, see: Shi et al., (2007, 2008). For reference structural data, see: Allen et al. (1987).

Experimental top

A mixture of 3,5-dihydroseleno-2-hydroxybenzaldehyde (564 mg, 2 mmol), cyclohexanamine (198 mg, 2 mmol) and CoCl₂.6H₂O (1 mmol, 238 mg) was stirred in acetonitrile (10 ml) for 1 h. After keeping the filtrate in air for 8 d, blue blocks of (I) were formed.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: XCAD4 (Harms & Wocadlo, 1995); 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 structure of the title compound (I) showing 30% probability displacement ellipsoids.

Bis(2-cyclohexyliminomethyl-4,6-dihydroselenophenolato)cobalt(II) acetonitrile solvate top

Crystal data top

[Co(C₁₃H₁₆NOSe₂)₂]·C₂H₃N	F(000) = 1612
M_r = 820.36	D_x = 1.716 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 25 reflections
a = 9.4745 (5) Å	θ = 9–12°
b = 16.3895 (5) Å	µ = 5.15 mm⁻¹
c = 20.4615 (5) Å	T = 298 K
β = 91.845 (2)°	Block, blue
V = 3175.7 (2) Å³	0.20 × 0.14 × 0.12 mm
Z = 4

Data collection top

Enraf–Nonius CAD-4 diffractometer	4034 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.043
Graphite monochromator	θ_max = 25.0°, θ_min = 1.6°
ω/2θ scans	h = −11→11
Absorption correction: ψ scan (North et al., 1968)	k = −19→19
T_min = 0.426, T_max = 0.577	l = −23→24
30082 measured reflections	200 standard reflections every 3 reflections
5592 independent reflections	intensity decay: 1%

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.141	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0729P)² + 2.8479P] where P = (F_o² + 2F_c²)/3
5592 reflections	(Δ/σ)_max < 0.001
348 parameters	Δρ_max = 0.88 e Å⁻³
0 restraints	Δρ_min = −0.83 e Å⁻³

Crystal data top

[Co(C₁₃H₁₆NOSe₂)₂]·C₂H₃N	V = 3175.7 (2) Å³
M_r = 820.36	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.4745 (5) Å	µ = 5.15 mm⁻¹
b = 16.3895 (5) Å	T = 298 K
c = 20.4615 (5) Å	0.20 × 0.14 × 0.12 mm
β = 91.845 (2)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	4034 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.043
T_min = 0.426, T_max = 0.577	200 standard reflections every 3 reflections
30082 measured reflections	intensity decay: 1%
5592 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.141	H-atom parameters constrained
S = 1.08	Δρ_max = 0.88 e Å⁻³
5592 reflections	Δρ_min = −0.83 e Å⁻³
348 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	0.71461 (6)	0.25063 (3)	0.18676 (3)	0.03902 (18)
Se1	0.78872 (10)	0.32963 (5)	0.40908 (3)	0.0967 (3)
H1	0.7785	0.3664	0.3821	0.145*
Se2	1.23778 (8)	0.10610 (5)	0.43164 (3)	0.0848 (2)
H2	1.3033	0.0961	0.4077	0.127*
Se3	0.26742 (7)	0.13073 (4)	0.12309 (4)	0.0831 (2)
H3A	0.3336	0.1105	0.1442	0.125*
Se4	0.14412 (10)	0.40993 (5)	−0.02853 (5)	0.1130 (3)
H4	0.1026	0.3769	−0.0523	0.169*
C1	0.8578 (5)	0.2201 (3)	0.3084 (2)	0.0512 (12)
C2	0.8960 (6)	0.2438 (3)	0.3727 (3)	0.0576 (13)
C3	1.0044 (6)	0.2114 (3)	0.4092 (3)	0.0630 (15)
H3	1.0245	0.2293	0.4516	0.076*
C4	1.0837 (6)	0.1511 (3)	0.3810 (3)	0.0568 (13)
C5	1.0558 (6)	0.1246 (3)	0.3186 (3)	0.0561 (13)
H5	1.1106	0.0835	0.3010	0.067*
C6	0.9441 (5)	0.1593 (3)	0.2806 (2)	0.0493 (12)
C7	0.9286 (5)	0.1301 (3)	0.2144 (2)	0.0520 (12)
H7	0.9847	0.0859	0.2034	0.062*
C8	0.8488 (6)	0.1210 (3)	0.1028 (2)	0.0590 (13)
H8	0.9382	0.0917	0.0987	0.071*
C9	0.8394 (8)	0.1865 (4)	0.0513 (3)	0.0756 (18)
H9A	0.9183	0.2237	0.0574	0.091*
H9B	0.7530	0.2174	0.0562	0.091*
C10	0.8410 (10)	0.1508 (5)	−0.0167 (3)	0.101 (3)
H10A	0.9304	0.1236	−0.0229	0.121*
H10B	0.8318	0.1944	−0.0487	0.121*
C11	0.7212 (10)	0.0904 (4)	−0.0274 (3)	0.106 (3)
H11A	0.7275	0.0658	−0.0703	0.127*
H11B	0.6316	0.1188	−0.0258	0.127*
C12	0.7271 (10)	0.0240 (4)	0.0245 (3)	0.096 (2)
H12A	0.8114	−0.0087	0.0195	0.115*
H12B	0.6457	−0.0115	0.0188	0.115*
C13	0.7288 (7)	0.0613 (4)	0.0934 (3)	0.0749 (17)
H13A	0.6399	0.0890	0.1001	0.090*
H13B	0.7385	0.0181	0.1257	0.090*
C14	0.4488 (5)	0.2682 (3)	0.1182 (2)	0.0471 (11)
C15	0.3182 (5)	0.2362 (3)	0.0947 (3)	0.0576 (13)
C16	0.2303 (6)	0.2780 (4)	0.0515 (3)	0.0655 (15)
H16	0.1455	0.2548	0.0368	0.079*
C17	0.2684 (6)	0.3539 (4)	0.0304 (3)	0.0653 (15)
C18	0.3922 (6)	0.3876 (4)	0.0509 (3)	0.0645 (14)
H18	0.4162	0.4393	0.0362	0.077*
C19	0.4854 (5)	0.3461 (3)	0.0941 (2)	0.0514 (12)
C20	0.6163 (6)	0.3879 (3)	0.1118 (3)	0.0573 (13)
H20	0.6259	0.4402	0.0949	0.069*
C21	0.8396 (6)	0.4181 (3)	0.1603 (3)	0.0614 (14)
H21	0.8476	0.4544	0.1225	0.074*
C22	0.9765 (6)	0.3710 (4)	0.1690 (4)	0.0810 (19)
H22A	0.9935	0.3400	0.1296	0.097*
H22B	0.9689	0.3329	0.2049	0.097*
C23	1.1006 (7)	0.4290 (5)	0.1830 (4)	0.096 (2)
H23A	1.1863	0.3975	0.1904	0.115*
H23B	1.1137	0.4638	0.1453	0.115*
C24	1.0754 (7)	0.4805 (5)	0.2413 (4)	0.096 (2)
H24A	1.1532	0.5184	0.2478	0.116*
H24B	1.0715	0.4461	0.2798	0.116*
C25	0.9388 (8)	0.5275 (5)	0.2329 (4)	0.102 (2)
H25A	0.9458	0.5654	0.1968	0.123*
H25B	0.9225	0.5587	0.2723	0.123*
C26	0.8150 (7)	0.4698 (4)	0.2196 (4)	0.084 (2)
H26A	0.8030	0.4348	0.2573	0.101*
H26B	0.7291	0.5013	0.2128	0.101*
C27	0.3987 (11)	0.2810 (6)	0.3050 (5)	0.129 (3)
H27A	0.4115	0.2561	0.2631	0.193*
H27B	0.3041	0.2714	0.3185	0.193*
H27C	0.4645	0.2580	0.3365	0.193*
C28	0.4218 (9)	0.3646 (6)	0.3003 (5)	0.114 (3)
N1	0.8459 (4)	0.1584 (3)	0.1690 (2)	0.0520 (10)
N2	0.7197 (4)	0.3621 (2)	0.14735 (19)	0.0513 (10)
N3	0.4406 (11)	0.4297 (7)	0.2980 (7)	0.198 (6)
O1	0.7504 (4)	0.2540 (2)	0.27880 (17)	0.0631 (10)
O2	0.5246 (4)	0.2252 (2)	0.15900 (18)	0.0597 (9)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co1	0.0356 (3)	0.0429 (3)	0.0382 (3)	0.0049 (3)	−0.0047 (2)	0.0054 (3)
Se1	0.1520 (7)	0.0796 (5)	0.0579 (4)	0.0525 (5)	−0.0053 (4)	−0.0112 (3)
Se2	0.0823 (5)	0.0871 (5)	0.0825 (5)	0.0177 (4)	−0.0361 (4)	0.0025 (4)
Se3	0.0677 (4)	0.0769 (4)	0.1036 (5)	−0.0214 (3)	−0.0137 (4)	0.0174 (4)
Se4	0.0972 (6)	0.1095 (6)	0.1279 (7)	0.0072 (5)	−0.0632 (5)	0.0329 (5)
C1	0.054 (3)	0.051 (3)	0.048 (3)	0.003 (2)	−0.004 (2)	0.005 (2)
C2	0.074 (4)	0.052 (3)	0.047 (3)	0.012 (3)	0.001 (3)	0.003 (2)
C3	0.087 (4)	0.051 (3)	0.050 (3)	0.001 (3)	−0.018 (3)	0.000 (2)
C4	0.056 (3)	0.053 (3)	0.059 (3)	0.000 (2)	−0.015 (3)	0.007 (2)
C5	0.055 (3)	0.050 (3)	0.063 (3)	0.006 (2)	−0.008 (3)	−0.003 (2)
C6	0.048 (3)	0.043 (3)	0.056 (3)	−0.001 (2)	−0.007 (2)	0.001 (2)
C7	0.048 (3)	0.056 (3)	0.052 (3)	0.007 (2)	−0.002 (2)	−0.003 (2)
C8	0.059 (3)	0.069 (3)	0.049 (3)	0.008 (3)	−0.003 (2)	−0.009 (3)
C9	0.106 (5)	0.069 (4)	0.053 (3)	−0.026 (3)	0.013 (3)	−0.005 (3)
C10	0.162 (8)	0.086 (5)	0.056 (4)	−0.018 (5)	0.023 (4)	0.004 (3)
C11	0.174 (8)	0.082 (5)	0.058 (4)	−0.013 (5)	−0.040 (4)	0.003 (3)
C12	0.151 (7)	0.067 (4)	0.068 (4)	−0.019 (4)	−0.015 (4)	−0.005 (3)
C13	0.109 (5)	0.057 (3)	0.058 (3)	−0.011 (3)	−0.009 (3)	0.008 (3)
C14	0.041 (3)	0.058 (3)	0.042 (3)	0.003 (2)	0.002 (2)	0.003 (2)
C15	0.048 (3)	0.068 (3)	0.056 (3)	0.004 (2)	−0.003 (2)	−0.003 (3)
C16	0.047 (3)	0.087 (4)	0.062 (3)	−0.003 (3)	−0.009 (3)	−0.005 (3)
C17	0.061 (4)	0.067 (4)	0.067 (4)	0.009 (3)	−0.016 (3)	0.008 (3)
C18	0.065 (4)	0.063 (3)	0.065 (3)	0.006 (3)	−0.011 (3)	0.008 (3)
C19	0.047 (3)	0.053 (3)	0.053 (3)	0.003 (2)	−0.008 (2)	0.004 (2)
C20	0.063 (3)	0.054 (3)	0.054 (3)	−0.001 (3)	−0.004 (3)	0.008 (2)
C21	0.062 (3)	0.057 (3)	0.064 (3)	−0.011 (3)	−0.009 (3)	0.011 (3)
C22	0.049 (3)	0.088 (4)	0.106 (5)	−0.009 (3)	0.004 (3)	−0.027 (4)
C23	0.060 (4)	0.106 (5)	0.121 (6)	−0.015 (4)	0.001 (4)	−0.031 (5)
C24	0.075 (5)	0.113 (6)	0.100 (5)	−0.030 (4)	0.000 (4)	−0.034 (5)
C25	0.087 (5)	0.092 (5)	0.130 (6)	−0.020 (4)	0.012 (5)	−0.046 (5)
C26	0.066 (4)	0.082 (4)	0.103 (5)	−0.005 (3)	0.002 (4)	−0.034 (4)
C27	0.153 (9)	0.122 (7)	0.115 (7)	−0.018 (6)	0.055 (6)	−0.023 (6)
C28	0.092 (6)	0.104 (7)	0.146 (8)	−0.022 (5)	0.003 (5)	0.023 (6)
N1	0.051 (2)	0.055 (2)	0.050 (2)	0.0023 (19)	−0.001 (2)	−0.0058 (19)
N2	0.047 (2)	0.055 (2)	0.052 (2)	−0.0031 (19)	−0.005 (2)	0.0063 (19)
N3	0.138 (8)	0.126 (7)	0.326 (17)	−0.033 (6)	−0.034 (9)	0.068 (9)
O1	0.066 (2)	0.075 (2)	0.048 (2)	0.0262 (19)	−0.0044 (18)	−0.0012 (17)
O2	0.051 (2)	0.062 (2)	0.066 (2)	−0.0037 (17)	−0.0102 (18)	0.0153 (18)

Geometric parameters (Å, º) top

Co1—O1	1.904 (3)	C12—H12B	0.9700
Co1—O2	1.916 (3)	C13—H13A	0.9700
Co1—N1	1.999 (4)	C13—H13B	0.9700
Co1—N2	1.999 (4)	C14—O2	1.293 (6)
Se1—C2	1.901 (5)	C14—C15	1.414 (7)
Se1—H1	0.8200	C14—C19	1.415 (7)
Se2—C4	1.910 (5)	C15—C16	1.377 (7)
Se2—H2	0.8200	C16—C17	1.368 (8)
Se3—C15	1.890 (6)	C16—H16	0.9300
Se3—H3A	0.8200	C17—C18	1.351 (8)
Se4—C17	1.896 (5)	C18—C19	1.405 (7)
Se4—H4	0.8200	C18—H18	0.9300
C1—O1	1.293 (6)	C19—C20	1.452 (7)
C1—C2	1.408 (7)	C20—N2	1.273 (6)
C1—C6	1.419 (7)	C20—H20	0.9300
C2—C3	1.359 (7)	C21—N2	1.477 (6)
C3—C4	1.379 (8)	C21—C26	1.504 (8)
C3—H3	0.9300	C21—C22	1.516 (8)
C4—C5	1.367 (7)	C21—H21	0.9800
C5—C6	1.413 (7)	C22—C23	1.532 (8)
C5—H5	0.9300	C22—H22A	0.9700
C6—C7	1.439 (7)	C22—H22B	0.9700
C7—N1	1.283 (6)	C23—C24	1.486 (10)
C7—H7	0.9300	C23—H23A	0.9700
C8—N1	1.487 (6)	C23—H23B	0.9700
C8—C9	1.505 (8)	C24—C25	1.511 (10)
C8—C13	1.508 (8)	C24—H24A	0.9700
C8—H8	0.9800	C24—H24B	0.9700
C9—C10	1.511 (9)	C25—C26	1.524 (9)
C9—H9A	0.9700	C25—H25A	0.9700
C9—H9B	0.9700	C25—H25B	0.9700
C10—C11	1.517 (10)	C26—H26A	0.9700
C10—H10A	0.9700	C26—H26B	0.9700
C10—H10B	0.9700	C27—C28	1.391 (13)
C11—C12	1.520 (9)	C27—H27A	0.9600
C11—H11A	0.9700	C27—H27B	0.9600
C11—H11B	0.9700	C27—H27C	0.9600
C12—C13	1.536 (9)	C28—N3	1.082 (11)
C12—H12A	0.9700

O1—Co1—O2	115.82 (16)	C16—C15—C14	122.5 (5)
O1—Co1—N1	96.32 (16)	C16—C15—Se3	119.8 (4)
O2—Co1—N1	111.45 (16)	C14—C15—Se3	117.6 (4)
O1—Co1—N2	111.50 (16)	C17—C16—C15	119.6 (5)
O2—Co1—N2	96.55 (15)	C17—C16—H16	120.2
N1—Co1—N2	126.51 (17)	C15—C16—H16	120.2
C2—Se1—H1	109.5	C18—C17—C16	120.6 (5)
C4—Se2—H2	109.5	C18—C17—Se4	120.9 (4)
C15—Se3—H3A	109.5	C16—C17—Se4	118.4 (4)
C17—Se4—H4	109.5	C17—C18—C19	121.2 (5)
O1—C1—C2	119.6 (5)	C17—C18—H18	119.4
O1—C1—C6	124.7 (4)	C19—C18—H18	119.4
C2—C1—C6	115.8 (4)	C18—C19—C14	120.0 (5)
C3—C2—C1	124.9 (5)	C18—C19—C20	116.2 (5)
C3—C2—Se1	118.6 (4)	C14—C19—C20	123.8 (4)
C1—C2—Se1	116.5 (4)	N2—C20—C19	128.4 (5)
C2—C3—C4	117.6 (5)	N2—C20—H20	115.8
C2—C3—H3	121.2	C19—C20—H20	115.8
C4—C3—H3	121.2	N2—C21—C26	110.9 (5)
C5—C4—C3	121.7 (5)	N2—C21—C22	110.8 (5)
C5—C4—Se2	120.4 (4)	C26—C21—C22	110.2 (5)
C3—C4—Se2	117.9 (4)	N2—C21—H21	108.3
C4—C5—C6	120.4 (5)	C26—C21—H21	108.3
C4—C5—H5	119.8	C22—C21—H21	108.3
C6—C5—H5	119.8	C21—C22—C23	110.8 (6)
C5—C6—C1	119.5 (5)	C21—C22—H22A	109.5
C5—C6—C7	115.8 (4)	C23—C22—H22A	109.5
C1—C6—C7	124.6 (4)	C21—C22—H22B	109.5
N1—C7—C6	127.1 (5)	C23—C22—H22B	109.5
N1—C7—H7	116.5	H22A—C22—H22B	108.1
C6—C7—H7	116.5	C24—C23—C22	111.1 (6)
N1—C8—C9	110.0 (4)	C24—C23—H23A	109.4
N1—C8—C13	110.3 (5)	C22—C23—H23A	109.4
C9—C8—C13	110.3 (5)	C24—C23—H23B	109.4
N1—C8—H8	108.7	C22—C23—H23B	109.4
C9—C8—H8	108.7	H23A—C23—H23B	108.0
C13—C8—H8	108.7	C23—C24—C25	111.0 (6)
C8—C9—C10	111.5 (5)	C23—C24—H24A	109.4
C8—C9—H9A	109.3	C25—C24—H24A	109.4
C10—C9—H9A	109.3	C23—C24—H24B	109.4
C8—C9—H9B	109.3	C25—C24—H24B	109.4
C10—C9—H9B	109.3	H24A—C24—H24B	108.0
H9A—C9—H9B	108.0	C24—C25—C26	110.8 (6)
C9—C10—C11	110.8 (6)	C24—C25—H25A	109.5
C9—C10—H10A	109.5	C26—C25—H25A	109.5
C11—C10—H10A	109.5	C24—C25—H25B	109.5
C9—C10—H10B	109.5	C26—C25—H25B	109.5
C11—C10—H10B	109.5	H25A—C25—H25B	108.1
H10A—C10—H10B	108.1	C21—C26—C25	110.8 (6)
C10—C11—C12	110.9 (6)	C21—C26—H26A	109.5
C10—C11—H11A	109.5	C25—C26—H26A	109.5
C12—C11—H11A	109.5	C21—C26—H26B	109.5
C10—C11—H11B	109.5	C25—C26—H26B	109.5
C12—C11—H11B	109.5	H26A—C26—H26B	108.1
H11A—C11—H11B	108.1	C28—C27—H27A	109.5
C11—C12—C13	110.8 (6)	C28—C27—H27B	109.5
C11—C12—H12A	109.5	H27A—C27—H27B	109.5
C13—C12—H12A	109.5	C28—C27—H27C	109.5
C11—C12—H12B	109.5	H27A—C27—H27C	109.5
C13—C12—H12B	109.5	H27B—C27—H27C	109.5
H12A—C12—H12B	108.1	N3—C28—C27	178.6 (14)
C8—C13—C12	111.1 (5)	C7—N1—C8	118.9 (4)
C8—C13—H13A	109.4	C7—N1—Co1	120.7 (3)
C12—C13—H13A	109.4	C8—N1—Co1	120.5 (3)
C8—C13—H13B	109.4	C20—N2—C21	118.0 (4)
C12—C13—H13B	109.4	C20—N2—Co1	120.3 (4)
H13A—C13—H13B	108.0	C21—N2—Co1	121.6 (3)
O2—C14—C15	118.6 (4)	C1—O1—Co1	124.3 (3)
O2—C14—C19	125.4 (4)	C14—O2—Co1	124.7 (3)
C15—C14—C19	116.0 (4)

O1—C1—C2—C3	178.5 (5)	C14—C19—C20—N2	3.8 (9)
C6—C1—C2—C3	−2.0 (8)	N2—C21—C22—C23	−179.5 (5)
O1—C1—C2—Se1	−3.1 (7)	C26—C21—C22—C23	−56.4 (8)
C6—C1—C2—Se1	176.4 (4)	C21—C22—C23—C24	56.5 (9)
C1—C2—C3—C4	0.4 (9)	C22—C23—C24—C25	−56.3 (9)
Se1—C2—C3—C4	−177.9 (4)	C23—C24—C25—C26	56.7 (9)
C2—C3—C4—C5	0.4 (8)	N2—C21—C26—C25	179.9 (6)
C2—C3—C4—Se2	179.3 (4)	C22—C21—C26—C25	56.9 (8)
C3—C4—C5—C6	0.5 (8)	C24—C25—C26—C21	−57.0 (9)
Se2—C4—C5—C6	−178.4 (4)	C6—C7—N1—C8	178.1 (5)
C4—C5—C6—C1	−2.1 (8)	C6—C7—N1—Co1	−2.2 (7)
C4—C5—C6—C7	176.8 (5)	C9—C8—N1—C7	−139.0 (5)
O1—C1—C6—C5	−177.8 (5)	C13—C8—N1—C7	99.1 (6)
C2—C1—C6—C5	2.7 (7)	C9—C8—N1—Co1	41.3 (6)
O1—C1—C6—C7	3.4 (8)	C13—C8—N1—Co1	−80.6 (5)
C2—C1—C6—C7	−176.1 (5)	O1—Co1—N1—C7	−7.3 (4)
C5—C6—C7—N1	−171.9 (5)	O2—Co1—N1—C7	−128.3 (4)
C1—C6—C7—N1	7.0 (8)	N2—Co1—N1—C7	115.4 (4)
N1—C8—C9—C10	−179.6 (6)	O1—Co1—N1—C8	172.4 (4)
C13—C8—C9—C10	−57.7 (7)	O2—Co1—N1—C8	51.4 (4)
C8—C9—C10—C11	57.4 (9)	N2—Co1—N1—C8	−64.9 (4)
C9—C10—C11—C12	−55.7 (9)	C19—C20—N2—C21	−177.5 (5)
C10—C11—C12—C13	54.8 (10)	C19—C20—N2—Co1	0.2 (8)
N1—C8—C13—C12	178.2 (5)	C26—C21—N2—C20	88.0 (6)
C9—C8—C13—C12	56.5 (7)	C22—C21—N2—C20	−149.2 (5)
C11—C12—C13—C8	−55.6 (9)	C26—C21—N2—Co1	−89.7 (5)
O2—C14—C15—C16	179.5 (5)	C22—C21—N2—Co1	33.0 (6)
C19—C14—C15—C16	−0.6 (8)	O1—Co1—N2—C20	−126.7 (4)
O2—C14—C15—Se3	−1.9 (6)	O2—Co1—N2—C20	−5.6 (4)
C19—C14—C15—Se3	177.9 (4)	N1—Co1—N2—C20	117.3 (4)
C14—C15—C16—C17	−0.6 (9)	O1—Co1—N2—C21	51.0 (4)
Se3—C15—C16—C17	−179.2 (4)	O2—Co1—N2—C21	172.0 (4)
C15—C16—C17—C18	0.9 (9)	N1—Co1—N2—C21	−65.1 (4)
C15—C16—C17—Se4	−179.6 (4)	C2—C1—O1—Co1	162.9 (4)
C16—C17—C18—C19	0.1 (9)	C6—C1—O1—Co1	−16.6 (7)
Se4—C17—C18—C19	−179.4 (4)	O2—Co1—O1—C1	134.1 (4)
C17—C18—C19—C14	−1.4 (8)	N1—Co1—O1—C1	16.5 (4)
C17—C18—C19—C20	178.9 (5)	N2—Co1—O1—C1	−116.9 (4)
O2—C14—C19—C18	−178.6 (5)	C15—C14—O2—Co1	170.8 (4)
C15—C14—C19—C18	1.6 (7)	C19—C14—O2—Co1	−9.0 (7)
O2—C14—C19—C20	1.0 (8)	O1—Co1—O2—C14	127.7 (4)
C15—C14—C19—C20	−178.8 (5)	N1—Co1—O2—C14	−123.5 (4)
C18—C19—C20—N2	−176.6 (6)	N2—Co1—O2—C14	10.0 (4)

Experimental details

Crystal data
Chemical formula	[Co(C₁₃H₁₆NOSe₂)₂]·C₂H₃N
M_r	820.36
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	9.4745 (5), 16.3895 (5), 20.4615 (5)
β (°)	91.845 (2)
V (Å³)	3175.7 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	5.15
Crystal size (mm)	0.20 × 0.14 × 0.12

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.426, 0.577
No. of measured, independent and observed [I > 2σ(I)] reflections	30082, 5592, 4034
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.141, 1.08
No. of reflections	5592
No. of parameters	348
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.88, −0.83

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Co1—O1	1.904 (3)	Co1—N1	1.999 (4)
Co1—O2	1.916 (3)	Co1—N2	1.999 (4)

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

Bis(2-cyclo­hexyl­imino­methyl-4,6-dihydro­seleno­phenolato)cobalt(II) acetonitrile solvate

Supporting information

Key indicators

checkCIF/PLATON results

Bis(2-cyclohexyliminomethyl-4,6-dihydroselenophenolato)cobalt(II) acetonitrile solvate