Bis(ethyl­enediamine-κ2N,N′)bis­(phenytoinato-κN)cobalt(II)

Hu, X.-L.; Xu, X.-Y.; Wang, D.-Q.; Zhou, Y.-Q.

doi:10.1107/S1600536809044092

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 11| November 2009| Page m1470

https://doi.org/10.1107/S1600536809044092

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Bis(ethylenediamine-κ²N,N′)bis(phenytoinato-κN)cobalt(II)

Xi-Lan Hu,^a ^* Xing-You Xu,^b Da-Qi Wang ^c and Yan-Qin Zhou ^a

^aHuaihai Institute of Technology, Jiangsu 222005, People's Republic of China, ^bHuaiyin Institute of Technology, Jiangsu 223003, People's Republic of China, and ^cCollege of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China
^*Correspondence e-mail: huxilan@hhit.edu.cn

(Received 19 October 2009; accepted 23 October 2009; online 31 October 2009)

The title compound [systematic name: bis(2,5-dioxo-4,4-diphenylimidazolidin-1-ido-κN¹)bis(ethylenediamine-κ²N,N′)cobalt(II)], [Co(C₁₅H₁₁N₂O₂)₂(C₂H₈N₂)₂], has site symmetry $[\overline{1}]$ . The Co^II cation is located on an inversion center and coordinated by two phenytoin anions and two ethylenediamine ligands in a distorted octahedral geometry. In the phenytoin anion, the two phenyl rings are twisted with respect to the central hydantoin ring, making dihedral angles of 77.49 (16) and 64.55 (15)°. Intramolecular and intermolecular N—H⋯O hydrogen bonding is present in the crystal structure.

Related literature

For applications of phenytoin, see: Akitsu & Einaga (2005 ); Akitsu et al. (1997 ). For related compounds, see: Hu et al. (2006 , 2007 ).

Experimental

Crystal data

[Co(C₁₅H₁₁N₂O₂)₂(C₂H₈N₂)₂]
M_r = 681.65
Monoclinic, P 2₁ /c
a = 11.8035 (12) Å
b = 12.3439 (13) Å
c = 11.0768 (10) Å
β = 92.277 (1)°
V = 1612.6 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.58 mm⁻¹
T = 298 K
0.52 × 0.42 × 0.28 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.751, T_max = 0.854
7877 measured reflections
2836 independent reflections
2201 reflections with I > 2σ(I)
R_int = 0.053

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.120
S = 1.08
2836 reflections
214 parameters
H-atom parameters constrained
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.63 e Å⁻³

Table 1
Selected bond lengths (Å)

Co1—N2	2.180 (2)
Co1—N3	2.123 (2)
Co1—N4	2.171 (2)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2ⁱ	0.86	2.00	2.861 (3)	173
N3—H3A⋯O1ⁱⁱ	0.90	2.18	2.947 (3)	143
N3—H3B⋯O2	0.90	2.20	2.966 (3)	143
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) -x+1, -y, -z.

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536809044092/xu2649sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809044092/xu2649Isup2.hkl

checkCIF report

Comment top

5,5-Diphenylimidazoline-2,4-dione (phenytoin) compound is a widely used drug in the treatment of epilepsy and should be an excellent ligand for transition metal complex (Akitsu et al., 1997; Akitsu & Einaga, 2005). We have synthesized a series of complexes with 5,5-diphenylhydantoinate ligand (Hu et al., 2006, 2007). We report here the crystal structure of the title compound.

The compound (Fig. 1) consists of [Co(pht)₂(en)₂] (Hpht = 5,5-diphenylhydantoin; en = ethylendiamine) complex neutral molecule. The Co atom is coordinated by two nitrogen atoms from two Hpht ligands and four nitrogen atoms from two en ligands in a distorted octahedral CoN₆ coordination environment (Table 1). The Co—N bond distances lie in the range of 2.123 (2) Å to 2.180 (2) Å. There are intra- and intermolecular N—H···O hydrogen bonds (Table 2).

Related literature top

For applications of phenytoin, see: Akitsu & Einaga (2005); Akitsu et al. (1997). For related compounds, see: Hu et al. (2006, 2007).

Experimental top

To a solution of Hpht (1 mmol) in methanol (10 ml) was added cobalt acetate tetrahydrate (0.5 mmol) and the solution of ethylenediamine (1 mmol) in methanol (10 ml). Then the mixture was sealed in a 25 ml stainless steel vessel with Teflon linear, and heated at 393 K for 50 h. After cooling to room temperature, the orange single crystals were obtained.

Structure description top

For applications of phenytoin, see: Akitsu & Einaga (2005); Akitsu et al. (1997). For related compounds, see: Hu et al. (2006, 2007).

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (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 complex. Displacement ellipsoids are drawn at the 30% probability level. The H-atom have been omitted for clarity.

bis(2,5-dioxo-4,4-diphenylimidazolidin-1-ido- κN¹)bis(ethylenediamine-κ²N,N')cobalt(II) top

Crystal data top

[Co(C₁₅H₁₁N₂O₂)₂(C₂H₈N₂)₂]	F(000) = 714
M_r = 681.65	D_x = 1.404 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3389 reflections
a = 11.8035 (12) Å	θ = 2.4–26.9°
b = 12.3439 (13) Å	µ = 0.58 mm⁻¹
c = 11.0768 (10) Å	T = 298 K
β = 92.277 (1)°	Block, orange
V = 1612.6 (3) Å³	0.52 × 0.42 × 0.28 mm
Z = 2

Data collection top

Bruker SMART CCD area-detector diffractometer	2836 independent reflections
Radiation source: fine-focus sealed tube	2201 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.053
φ and ω scans	θ_max = 25.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→11
T_min = 0.751, T_max = 0.854	k = −14→14
7877 measured reflections	l = −13→12

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.120	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0528P)² + 0.9459P] where P = (F_o² + 2F_c²)/3
2836 reflections	(Δ/σ)_max = 0.001
214 parameters	Δρ_max = 0.45 e Å⁻³
0 restraints	Δρ_min = −0.63 e Å⁻³

Crystal data top

[Co(C₁₅H₁₁N₂O₂)₂(C₂H₈N₂)₂]	V = 1612.6 (3) Å³
M_r = 681.65	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.8035 (12) Å	µ = 0.58 mm⁻¹
b = 12.3439 (13) Å	T = 298 K
c = 11.0768 (10) Å	0.52 × 0.42 × 0.28 mm
β = 92.277 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2836 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2201 reflections with I > 2σ(I)
T_min = 0.751, T_max = 0.854	R_int = 0.053
7877 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.120	H-atom parameters constrained
S = 1.08	Δρ_max = 0.45 e Å⁻³
2836 reflections	Δρ_min = −0.63 e Å⁻³
214 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.5000	0.0000	0.0000	0.02790 (18)
N1	0.69362 (19)	0.2364 (2)	0.21879 (19)	0.0366 (6)
H1	0.7028	0.2732	0.2843	0.044*
N2	0.61498 (18)	0.11950 (18)	0.08239 (18)	0.0300 (5)
N3	0.63769 (19)	−0.0802 (2)	−0.0794 (2)	0.0412 (6)
H3A	0.6163	−0.1046	−0.1534	0.049*
H3B	0.6959	−0.0339	−0.0869	0.049*
N4	0.5465 (2)	−0.1072 (2)	0.1492 (2)	0.0437 (6)
H4A	0.5499	−0.0702	0.2193	0.052*
H4B	0.4951	−0.1606	0.1549	0.052*
O1	0.53186 (17)	0.14774 (19)	0.26695 (18)	0.0513 (6)
O2	0.74262 (16)	0.13811 (15)	−0.06839 (15)	0.0335 (5)
C1	0.6080 (2)	0.1661 (2)	0.1968 (2)	0.0336 (6)
C2	0.7082 (2)	0.1602 (2)	0.0329 (2)	0.0277 (6)
C3	0.7685 (2)	0.2423 (2)	0.1181 (2)	0.0304 (6)
C4	0.7646 (2)	0.3540 (2)	0.0582 (2)	0.0353 (7)
C5	0.6736 (3)	0.4219 (3)	0.0689 (4)	0.0608 (10)
H5	0.6148	0.4013	0.1174	0.073*
C6	0.6674 (4)	0.5196 (3)	0.0096 (5)	0.0799 (13)
H6	0.6046	0.5642	0.0177	0.096*
C7	0.7544 (4)	0.5513 (3)	−0.0617 (3)	0.0715 (12)
H7	0.7504	0.6174	−0.1019	0.086*
C8	0.8464 (4)	0.4856 (3)	−0.0734 (3)	0.0688 (12)
H8	0.9051	0.5067	−0.1217	0.083*
C9	0.8516 (3)	0.3875 (3)	−0.0129 (3)	0.0538 (9)
H9	0.9148	0.3434	−0.0203	0.065*
C10	0.8891 (2)	0.2084 (2)	0.1586 (2)	0.0329 (6)
C11	0.9473 (3)	0.2721 (3)	0.2414 (3)	0.0527 (9)
H11	0.9147	0.3362	0.2674	0.063*
C12	1.0538 (3)	0.2423 (4)	0.2868 (3)	0.0681 (11)
H12	1.0921	0.2864	0.3430	0.082*
C13	1.1027 (3)	0.1489 (4)	0.2494 (3)	0.0681 (12)
H13	1.1735	0.1282	0.2812	0.082*
C14	1.0475 (3)	0.0858 (3)	0.1654 (3)	0.0618 (10)
H14	1.0817	0.0231	0.1380	0.074*
C15	0.9402 (3)	0.1147 (3)	0.1204 (3)	0.0473 (8)
H15	0.9025	0.0705	0.0640	0.057*
C16	0.6722 (4)	−0.1698 (4)	−0.0025 (4)	0.0868 (14)
H16A	0.6294	−0.2335	−0.0277	0.104*
H16B	0.7517	−0.1849	−0.0143	0.104*
C17	0.6569 (4)	−0.1520 (4)	0.1242 (4)	0.0873 (15)
H17A	0.7153	−0.1028	0.1551	0.105*
H17B	0.6665	−0.2202	0.1668	0.105*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co1	0.0217 (3)	0.0286 (3)	0.0338 (3)	0.0002 (2)	0.00614 (19)	−0.0021 (2)
N1	0.0347 (13)	0.0453 (15)	0.0303 (12)	−0.0069 (11)	0.0082 (10)	−0.0116 (11)
N2	0.0266 (12)	0.0330 (13)	0.0308 (11)	−0.0021 (10)	0.0062 (9)	−0.0046 (10)
N3	0.0299 (13)	0.0402 (14)	0.0542 (14)	−0.0011 (11)	0.0085 (11)	−0.0106 (12)
N4	0.0394 (14)	0.0436 (16)	0.0480 (14)	−0.0049 (12)	0.0015 (11)	0.0072 (12)
O1	0.0414 (12)	0.0723 (17)	0.0415 (11)	−0.0166 (11)	0.0190 (10)	−0.0120 (11)
O2	0.0405 (11)	0.0343 (11)	0.0261 (9)	−0.0047 (9)	0.0082 (8)	−0.0015 (8)
C1	0.0287 (14)	0.0389 (17)	0.0334 (14)	−0.0016 (13)	0.0036 (11)	−0.0003 (12)
C2	0.0295 (14)	0.0256 (14)	0.0281 (13)	−0.0009 (11)	0.0035 (11)	0.0019 (11)
C3	0.0297 (14)	0.0312 (15)	0.0306 (13)	−0.0040 (12)	0.0066 (11)	−0.0051 (11)
C4	0.0392 (16)	0.0277 (15)	0.0390 (15)	−0.0049 (13)	0.0019 (12)	−0.0058 (12)
C5	0.048 (2)	0.047 (2)	0.088 (3)	0.0023 (17)	0.0093 (19)	0.009 (2)
C6	0.075 (3)	0.048 (3)	0.116 (4)	0.015 (2)	−0.003 (3)	0.014 (2)
C7	0.114 (4)	0.034 (2)	0.066 (2)	−0.003 (2)	−0.001 (2)	0.0057 (19)
C8	0.109 (4)	0.042 (2)	0.057 (2)	−0.009 (2)	0.029 (2)	0.0037 (17)
C9	0.069 (2)	0.0373 (19)	0.0565 (19)	0.0007 (17)	0.0248 (17)	0.0010 (16)
C10	0.0281 (14)	0.0396 (17)	0.0314 (14)	−0.0046 (13)	0.0058 (11)	0.0019 (12)
C11	0.0349 (17)	0.066 (2)	0.0576 (19)	−0.0035 (17)	0.0022 (14)	−0.0179 (17)
C12	0.0347 (19)	0.107 (3)	0.062 (2)	−0.011 (2)	−0.0046 (16)	−0.019 (2)
C13	0.0327 (18)	0.110 (4)	0.062 (2)	0.006 (2)	−0.0013 (17)	0.013 (2)
C14	0.047 (2)	0.063 (2)	0.075 (2)	0.0152 (19)	0.0041 (18)	0.007 (2)
C15	0.0419 (18)	0.047 (2)	0.0531 (18)	0.0017 (16)	−0.0014 (14)	−0.0023 (16)
C16	0.079 (3)	0.077 (3)	0.106 (4)	0.046 (3)	0.026 (3)	0.009 (3)
C17	0.072 (3)	0.094 (4)	0.097 (3)	0.043 (3)	0.011 (2)	0.037 (3)

Geometric parameters (Å, º) top

Co1—N2ⁱ	2.180 (2)	C5—H5	0.9300
Co1—N2	2.180 (2)	C6—C7	1.377 (6)
Co1—N3	2.123 (2)	C6—H6	0.9300
Co1—N3ⁱ	2.123 (2)	C7—C8	1.365 (6)
Co1—N4ⁱ	2.171 (2)	C7—H7	0.9300
Co1—N4	2.171 (2)	C8—C9	1.384 (5)
N1—C1	1.347 (3)	C8—H8	0.9300
N1—C3	1.452 (3)	C9—H9	0.9300
N1—H1	0.8600	C10—C11	1.372 (4)
N2—C2	1.346 (3)	C10—C15	1.378 (4)
N2—C1	1.397 (3)	C11—C12	1.386 (5)
N3—C16	1.444 (5)	C11—H11	0.9300
N3—H3A	0.9000	C12—C13	1.362 (6)
N3—H3B	0.9000	C12—H12	0.9300
N4—C17	1.452 (5)	C13—C14	1.359 (5)
N4—H4A	0.9000	C13—H13	0.9300
N4—H4B	0.9000	C14—C15	1.389 (5)
O1—C1	1.232 (3)	C14—H14	0.9300
O2—C2	1.239 (3)	C15—H15	0.9300
C2—C3	1.540 (4)	C16—C17	1.439 (6)
C3—C4	1.530 (4)	C16—H16A	0.9700
C3—C10	1.533 (4)	C16—H16B	0.9700
C4—C5	1.371 (4)	C17—H17A	0.9700
C4—C9	1.383 (4)	C17—H17B	0.9700
C5—C6	1.374 (5)

N3—Co1—N3ⁱ	180.00 (17)	C9—C4—C3	120.4 (3)
N3—Co1—N4ⁱ	98.26 (10)	C4—C5—C6	121.5 (4)
N3ⁱ—Co1—N4ⁱ	81.74 (10)	C4—C5—H5	119.2
N3—Co1—N4	81.74 (10)	C6—C5—H5	119.2
N3ⁱ—Co1—N4	98.26 (10)	C5—C6—C7	119.8 (4)
N4ⁱ—Co1—N4	180.00 (13)	C5—C6—H6	120.1
N3—Co1—N2ⁱ	89.15 (9)	C7—C6—H6	120.1
N3ⁱ—Co1—N2ⁱ	90.85 (9)	C8—C7—C6	120.0 (4)
N4ⁱ—Co1—N2ⁱ	87.67 (9)	C8—C7—H7	120.0
N4—Co1—N2ⁱ	92.33 (9)	C6—C7—H7	120.0
N3—Co1—N2	90.85 (9)	C7—C8—C9	119.6 (4)
N3ⁱ—Co1—N2	89.15 (9)	C7—C8—H8	120.2
N4ⁱ—Co1—N2	92.33 (9)	C9—C8—H8	120.2
N4—Co1—N2	87.67 (9)	C4—C9—C8	121.2 (4)
N2ⁱ—Co1—N2	180.00 (13)	C4—C9—H9	119.4
C1—N1—C3	111.7 (2)	C8—C9—H9	119.4
C1—N1—H1	124.2	C11—C10—C15	118.2 (3)
C3—N1—H1	124.2	C11—C10—C3	118.2 (3)
C2—N2—C1	107.1 (2)	C15—C10—C3	123.5 (3)
C2—N2—Co1	125.97 (16)	C10—C11—C12	120.9 (4)
C1—N2—Co1	126.87 (17)	C10—C11—H11	119.5
C16—N3—Co1	108.4 (2)	C12—C11—H11	119.5
C16—N3—H3A	110.0	C13—C12—C11	120.2 (4)
Co1—N3—H3A	110.0	C13—C12—H12	119.9
C16—N3—H3B	110.0	C11—C12—H12	119.9
Co1—N3—H3B	110.0	C14—C13—C12	119.8 (3)
H3A—N3—H3B	108.4	C14—C13—H13	120.1
C17—N4—Co1	106.7 (2)	C12—C13—H13	120.1
C17—N4—H4A	110.4	C13—C14—C15	120.2 (4)
Co1—N4—H4A	110.4	C13—C14—H14	119.9
C17—N4—H4B	110.4	C15—C14—H14	119.9
Co1—N4—H4B	110.4	C10—C15—C14	120.6 (3)
H4A—N4—H4B	108.6	C10—C15—H15	119.7
O1—C1—N1	124.4 (3)	C14—C15—H15	119.7
O1—C1—N2	124.6 (3)	C17—C16—N3	114.5 (3)
N1—C1—N2	111.0 (2)	C17—C16—H16A	108.6
O2—C2—N2	126.1 (2)	N3—C16—H16A	108.6
O2—C2—C3	122.7 (2)	C17—C16—H16B	108.6
N2—C2—C3	111.2 (2)	N3—C16—H16B	108.6
N1—C3—C4	111.7 (2)	H16A—C16—H16B	107.6
N1—C3—C10	110.4 (2)	C16—C17—N4	113.1 (3)
C4—C3—C10	112.6 (2)	C16—C17—H17A	109.0
N1—C3—C2	99.0 (2)	N4—C17—H17A	109.0
C4—C3—C2	108.7 (2)	C16—C17—H17B	109.0
C10—C3—C2	113.6 (2)	N4—C17—H17B	109.0
C5—C4—C9	117.9 (3)	H17A—C17—H17B	107.8
C5—C4—C3	121.6 (3)

N3—Co1—N2—C2	36.0 (2)	O2—C2—C3—C4	63.0 (3)
N3ⁱ—Co1—N2—C2	−144.0 (2)	N2—C2—C3—C4	−115.9 (2)
N4ⁱ—Co1—N2—C2	−62.3 (2)	O2—C2—C3—C10	−63.3 (3)
N4—Co1—N2—C2	117.7 (2)	N2—C2—C3—C10	117.7 (2)
N2ⁱ—Co1—N2—C2	−164 (100)	N1—C3—C4—C5	−22.4 (4)
N3—Co1—N2—C1	−142.2 (2)	C10—C3—C4—C5	−147.3 (3)
N3ⁱ—Co1—N2—C1	37.8 (2)	C2—C3—C4—C5	85.8 (3)
N4ⁱ—Co1—N2—C1	119.5 (2)	N1—C3—C4—C9	160.3 (3)
N4—Co1—N2—C1	−60.5 (2)	C10—C3—C4—C9	35.4 (4)
N2ⁱ—Co1—N2—C1	18 (100)	C2—C3—C4—C9	−91.5 (3)
N3ⁱ—Co1—N3—C16	63 (100)	C9—C4—C5—C6	1.0 (5)
N4ⁱ—Co1—N3—C16	−170.8 (3)	C3—C4—C5—C6	−176.4 (3)
N4—Co1—N3—C16	9.2 (3)	C4—C5—C6—C7	−0.5 (7)
N2ⁱ—Co1—N3—C16	−83.3 (3)	C5—C6—C7—C8	0.0 (7)
N2—Co1—N3—C16	96.7 (3)	C6—C7—C8—C9	−0.2 (6)
N3—Co1—N4—C17	13.2 (3)	C5—C4—C9—C8	−1.2 (5)
N3ⁱ—Co1—N4—C17	−166.8 (3)	C3—C4—C9—C8	176.2 (3)
N4ⁱ—Co1—N4—C17	−140 (100)	C7—C8—C9—C4	0.8 (6)
N2ⁱ—Co1—N4—C17	102.0 (3)	N1—C3—C10—C11	−65.3 (3)
N2—Co1—N4—C17	−78.0 (3)	C4—C3—C10—C11	60.3 (3)
C3—N1—C1—O1	−178.6 (3)	C2—C3—C10—C11	−175.5 (3)
C3—N1—C1—N2	−0.7 (3)	N1—C3—C10—C15	111.6 (3)
C2—N2—C1—O1	179.1 (3)	C4—C3—C10—C15	−122.8 (3)
Co1—N2—C1—O1	−2.4 (4)	C2—C3—C10—C15	1.5 (4)
C2—N2—C1—N1	1.1 (3)	C15—C10—C11—C12	−1.0 (5)
Co1—N2—C1—N1	179.62 (18)	C3—C10—C11—C12	176.2 (3)
C1—N2—C2—O2	180.0 (3)	C10—C11—C12—C13	0.2 (6)
Co1—N2—C2—O2	1.5 (4)	C11—C12—C13—C14	1.3 (6)
C1—N2—C2—C3	−1.1 (3)	C12—C13—C14—C15	−1.9 (6)
Co1—N2—C2—C3	−179.66 (16)	C11—C10—C15—C14	0.3 (5)
C1—N1—C3—C4	114.4 (3)	C3—C10—C15—C14	−176.6 (3)
C1—N1—C3—C10	−119.5 (3)	C13—C14—C15—C10	1.1 (5)
C1—N1—C3—C2	0.0 (3)	Co1—N3—C16—C17	−31.8 (5)
O2—C2—C3—N1	179.7 (2)	N3—C16—C17—N4	46.5 (6)
N2—C2—C3—N1	0.7 (3)	Co1—N4—C17—C16	−34.6 (5)

Symmetry code: (i) −x+1, −y, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2ⁱⁱ	0.86	2.00	2.861 (3)	173
N3—H3A···O1ⁱ	0.90	2.18	2.947 (3)	143
N3—H3B···O2	0.90	2.20	2.966 (3)	143

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

Experimental details

Crystal data
Chemical formula	[Co(C₁₅H₁₁N₂O₂)₂(C₂H₈N₂)₂]
M_r	681.65
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	11.8035 (12), 12.3439 (13), 11.0768 (10)
β (°)	92.277 (1)
V (Å³)	1612.6 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.58
Crystal size (mm)	0.52 × 0.42 × 0.28

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.751, 0.854
No. of measured, independent and observed [I > 2σ(I)] reflections	7877, 2836, 2201
R_int	0.053
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.120, 1.08
No. of reflections	2836
No. of parameters	214
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.63

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Co1—N2	2.180 (2)	Co1—N4	2.171 (2)
Co1—N3	2.123 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2ⁱ	0.86	2.00	2.861 (3)	173.4
N3—H3A···O1ⁱⁱ	0.90	2.18	2.947 (3)	142.8
N3—H3B···O2	0.90	2.20	2.966 (3)	142.5

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

Acknowledgements

We are grateful for financial support from the Key Project for Fundamental Research of the Education Committee of Jiangsu Province (07KJA15011) and the Natural Science Foundation of Huaihai Institute of Technology, China (KX07042).

References

Akitsu, T. & Einaga, Y. (2005). Acta Cryst. C61, m183–m186. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Akitsu, T., Komorita, S., Kushi, Y., Li, C., Kanehisa, N. & Kai, Y. (1997). Bull. Chem. Soc. Jpn, 70, 821–827. CrossRef CAS Web of Science Google Scholar
Hu, X.-L., Xu, X.-Y., Wang, D.-Q., Liu, H.-F. & Ying, F.-J. (2007). Acta Cryst. E63, m405–m406. Web of Science CSD CrossRef IUCr Journals Google Scholar
Hu, X.-L., Xu, X.-Y., Liu, H.-F., Xu, T.-T. & Wang, D.-Q. (2006). Acta Cryst. E62, m2976–m2977. 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
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar