Bis(2,4-dioxo-5,5-diphenyl­imidazol­idin­ido-κN3)bis­(propane-1,3-diamine-κ2N,N′)cobalt(II)

Hu, X.; Jiang, Q.; Wang, D.; Liu, H.

doi:10.1107/S1600536811050252

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 12| December 2011| Page m1885

https://doi.org/10.1107/S1600536811050252

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Bis(2,4-dioxo-5,5-diphenylimidazolidinido-κN³)bis(propane-1,3-diamine-κ²N,N′)cobalt(II)

Xilan Hu,^a ^* Qing Jiang,^a Daqi Wang ^b and Haifeng Liu ^a

^aHuaihai Institute of Technology, Jiangsu 222005, People's Republic of China, and ^bCollege of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China
^*Correspondence e-mail: huxilan836@sohu.com

(Received 9 November 2011; accepted 23 November 2011; online 30 November 2011)

The complex molecule of the title compound, [Co(C₁₅H₁₁N₂O₂)₂(C₃H₁₀N₂)₂], has crystallographically imposed inversion symmetry. The Co^II atom displays a distorted octahedral coordination geometry. In the phenytoin anion, the two phenyl rings form dihedral angles of 62.26 (8) and 57.47 (9)° with the central imidazole ring. Intramolecular N—H⋯O and C—H⋯O hydrogen bonds occur. In the crystal, N—H⋯O and C—H⋯O hydrogen bonds forming a three-dimensional network.

Related literature

For applications of phenytoin, see: Milne et al. (1999 ); Akitsu et al. (1997 ); Akitsu & Einaga (2005 ). For related structures, see: Hu et al. (2006 , 2007 , 2009 )

Experimental

Crystal data

[Co(C₁₅H₁₁N₂O₂)₂(C₃H₁₀N₂)₂]
M_r = 709.71
Monoclinic, P 2₁ /n
a = 10.0368 (12) Å
b = 8.7865 (9) Å
c = 20.684 (2) Å
β = 102.363 (2)°
V = 1781.8 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.53 mm⁻¹
T = 298 K
0.50 × 0.46 × 0.45 mm

Data collection

Siemens SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.777, T_max = 0.796
8632 measured reflections
3130 independent reflections
2536 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.097
S = 1.05
3130 reflections
224 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—N2	2.1531 (16)
Co1—N4	2.165 (2)
Co1—N3	2.180 (2)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯O1	0.90	2.35	3.061 (3)	136
N4—H4B⋯O2	0.90	2.38	3.095 (3)	137
C5—H5⋯O2	0.93	2.46	3.089 (3)	125
N1—H1⋯O1ⁱ	0.86	2.02	2.825 (2)	156
N3—H3B⋯O2ⁱⁱ	0.90	2.34	3.057 (3)	137
N4—H4A⋯O1ⁱⁱ	0.90	2.27	2.979 (3)	136
C6—H6⋯O2ⁱⁱⁱ	0.93	2.39	3.293 (3)	165
Symmetry codes: (i) -x+2, -y+1, -z; (ii) -x+1, -y+1, -z; (iii) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); 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 I, global. DOI: https://doi.org/10.1107/S1600536811050252/rz2670sup1.cif

Supporting information file. DOI: https://doi.org/10.1107/S1600536811050252/rz2670Isup2.mol

Supporting information file. DOI: https://doi.org/10.1107/S1600536811050252/rz2670Isup4.mol

Supporting information file. DOI: https://doi.org/10.1107/S1600536811050252/rz2670Isup5.cdx

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811050252/rz2670Isup7.hkl

checkCIF report

Comment top

5,5-Diphenylimidazoline-2,4-dione (phenytoin) is a widely used drug in the treatment of epilepsy and an excellent ligand for transition metal complexes (Milne et al., 1999; Akitsu et al., 1997; Akitsu & Einaga, 2005). As a continuation of our research devoted to the design and synthesis of complexes with 5,5-diphenylhydantoinate (Hu et al., 2006, 2007, 2009), we report here the crystal structure of the title compound.

The title compound (Fig. 1) consists of [Co(pht)₂(pa)₂] (Hpht = 5,5-diphenylhydantoin; pa = 1,3-propylendiamine) neutral complex molecules having crystallographically imposed inversion symmetry. The Co atom is coordinated by two nitrogen atoms from two pht anions and four nitrogen atoms from two pa ligands in a distorted octahedral CoN₆ coordination geometry. The Co—N bond distances lie in the range 2.153 (2)–2.180 (2) Å. The imidazole ring (N1/N2/C1–C3) is approximately planar (maximum deviation 0.025 (3) Å for atoms C3) and forms dihedral angles of 62.26 (8) and 57.47 (9)° with the C4–C9 and C10–C15 phenyl rings, respectively. In the crystal structure, intra- and intermolecular N—H···O and C—H···O hydrogen bonds are observed (Table 1), forming a three-dimensional network.

Related literature top

For applications of phenytoin, see: Milne et al. (1999); Akitsu et al. (1997); Akitsu & Einaga (2005). For related structures, see: Hu et al. (2006, 2007, 2009)

Experimental top

To a solution of 5,5-diphenylhydantoin (1.00 mmol) in methanol (10 ml) was added cobalt(II) acetate tetrahydrate (0.5 mmol) and a solution of 1,3-propylendiamine (1 mmol) in methanol (10 ml). Then the mixture was sealed in a 25 ml stainless steel vessel with Teflon liner and heated to 393 K for 50 h, the fill rate being 80%. After cooling to room temperature, orange single crystals of the title compound suitable for X-ray analysis were obtained.

Structure description top

For applications of phenytoin, see: Milne et al. (1999); Akitsu et al. (1997); Akitsu & Einaga (2005). For related structures, see: Hu et al. (2006, 2007, 2009)

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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 complex showing displacement ellipsoids drawn at the 30% probability level. H-atom are omitted for clarity. Unlabelled atoms are related to the labelled atoms by the symmetry operation 1-x, 1-y, -z.

Bis(2,4-dioxo-5,5-diphenylimidazolidinido-κN³)bis(propane-1,3- diamine-κ²N,N')cobalt(II) top

Crystal data top

[Co(C₁₅H₁₁N₂O₂)₂(C₃H₁₀N₂)₂]	F(000) = 746
M_r = 709.71	D_x = 1.323 Mg m⁻³
Monoclinic, P2₁/n	Melting point = 534–536 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 10.0368 (12) Å	Cell parameters from 4059 reflections
b = 8.7865 (9) Å	θ = 2.5–27.9°
c = 20.684 (2) Å	µ = 0.53 mm⁻¹
β = 102.363 (2)°	T = 298 K
V = 1781.8 (3) Å³	Block, orange
Z = 2	0.50 × 0.46 × 0.45 mm

Data collection top

Siemens SMART CCD area-detector diffractometer	3130 independent reflections
Radiation source: fine-focus sealed tube	2536 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
phi and ω scans	θ_max = 25.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
T_min = 0.777, T_max = 0.796	k = −10→10
8632 measured reflections	l = −19→24

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.036	H-atom parameters constrained
wR(F²) = 0.097	w = 1/[σ²(F_o²) + (0.0364P)² + 1.1953P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
3130 reflections	Δρ_max = 0.24 e Å⁻³
224 parameters	Δρ_min = −0.22 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0318 (15)

Crystal data top

[Co(C₁₅H₁₁N₂O₂)₂(C₃H₁₀N₂)₂]	V = 1781.8 (3) Å³
M_r = 709.71	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.0368 (12) Å	µ = 0.53 mm⁻¹
b = 8.7865 (9) Å	T = 298 K
c = 20.684 (2) Å	0.50 × 0.46 × 0.45 mm
β = 102.363 (2)°

Data collection top

Siemens SMART CCD area-detector diffractometer	3130 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2536 reflections with I > 2σ(I)
T_min = 0.777, T_max = 0.796	R_int = 0.026
8632 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.097	H-atom parameters constrained
S = 1.05	Δρ_max = 0.24 e Å⁻³
3130 reflections	Δρ_min = −0.22 e Å⁻³
224 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	0.5000	0.5000	0.0000	0.03637 (17)
N1	0.92944 (16)	0.6118 (2)	0.05822 (9)	0.0418 (5)
H1	1.0091	0.6117	0.0491	0.050*
N2	0.70243 (16)	0.5782 (2)	0.04395 (9)	0.0412 (5)
N3	0.5249 (2)	0.5748 (3)	−0.09720 (10)	0.0615 (6)
H3A	0.6148	0.5873	−0.0949	0.074*
H3B	0.4972	0.4981	−0.1258	0.074*
N4	0.4168 (2)	0.7172 (3)	0.02120 (11)	0.0583 (6)
H4A	0.3484	0.6978	0.0419	0.070*
H4B	0.4822	0.7657	0.0505	0.070*
O1	0.81717 (15)	0.4817 (2)	−0.03302 (8)	0.0642 (6)
O2	0.66668 (15)	0.6952 (2)	0.13808 (8)	0.0539 (5)
C1	0.8178 (2)	0.5516 (3)	0.01896 (11)	0.0435 (6)
C2	0.7420 (2)	0.6519 (3)	0.10189 (11)	0.0392 (5)
C3	0.89906 (19)	0.6768 (3)	0.11802 (10)	0.0350 (5)
C4	0.9728 (2)	0.5888 (3)	0.17903 (11)	0.0370 (5)
C5	0.9063 (3)	0.5142 (3)	0.22210 (12)	0.0478 (6)
H5	0.8117	0.5177	0.2147	0.057*
C6	0.9794 (3)	0.4346 (3)	0.27608 (14)	0.0630 (7)
H6	0.9333	0.3851	0.3045	0.076*
C7	1.1180 (4)	0.4283 (4)	0.28789 (15)	0.0725 (9)
H7	1.1664	0.3750	0.3242	0.087*
C8	1.1861 (3)	0.5014 (4)	0.24573 (17)	0.0729 (9)
H8	1.2808	0.4970	0.2534	0.087*
C9	1.1138 (2)	0.5813 (3)	0.19190 (13)	0.0555 (7)
H9	1.1607	0.6309	0.1639	0.067*
C10	0.9329 (2)	0.8457 (3)	0.12697 (11)	0.0405 (5)
C11	1.0033 (3)	0.9222 (3)	0.08683 (14)	0.0627 (7)
H11	1.0304	0.8712	0.0524	0.075*
C12	1.0341 (4)	1.0768 (4)	0.09782 (17)	0.0823 (10)
H12	1.0823	1.1282	0.0708	0.099*
C13	0.9935 (3)	1.1521 (4)	0.14804 (17)	0.0768 (10)
H13	1.0125	1.2553	0.1545	0.092*
C14	0.9256 (3)	1.0773 (3)	0.18856 (16)	0.0663 (8)
H14	0.8990	1.1289	0.2230	0.080*
C15	0.8962 (2)	0.9249 (3)	0.17859 (13)	0.0514 (6)
H15	0.8508	0.8741	0.2069	0.062*
C16	0.4548 (6)	0.7161 (5)	−0.12703 (18)	0.1266 (19)
H16A	0.3618	0.6906	−0.1486	0.152*
H16B	0.5005	0.7526	−0.1609	0.152*
C17	0.4511 (6)	0.8423 (5)	−0.0788 (2)	0.1254 (17)
H17A	0.5435	0.8589	−0.0540	0.150*
H17B	0.4228	0.9343	−0.1039	0.150*
C18	0.3650 (5)	0.8236 (4)	−0.0320 (2)	0.1069 (15)
H18A	0.2760	0.7890	−0.0555	0.128*
H18B	0.3529	0.9220	−0.0128	0.128*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co1	0.0217 (2)	0.0489 (3)	0.0374 (3)	0.00008 (18)	0.00402 (16)	−0.0121 (2)
N1	0.0222 (9)	0.0644 (13)	0.0398 (10)	−0.0066 (8)	0.0089 (7)	−0.0201 (9)
N2	0.0228 (9)	0.0589 (13)	0.0419 (10)	−0.0021 (8)	0.0073 (7)	−0.0200 (9)
N3	0.0480 (12)	0.0901 (18)	0.0444 (12)	−0.0201 (12)	0.0055 (9)	−0.0083 (12)
N4	0.0365 (11)	0.0634 (15)	0.0690 (15)	0.0073 (10)	−0.0021 (10)	−0.0241 (12)
O1	0.0278 (8)	0.1144 (17)	0.0514 (10)	−0.0071 (9)	0.0108 (7)	−0.0475 (11)
O2	0.0294 (8)	0.0796 (13)	0.0547 (10)	−0.0015 (8)	0.0131 (7)	−0.0340 (9)
C1	0.0249 (10)	0.0628 (16)	0.0426 (13)	−0.0021 (10)	0.0068 (9)	−0.0168 (11)
C2	0.0266 (10)	0.0497 (14)	0.0410 (12)	−0.0001 (10)	0.0068 (9)	−0.0134 (11)
C3	0.0243 (10)	0.0445 (13)	0.0361 (11)	−0.0024 (9)	0.0062 (8)	−0.0114 (10)
C4	0.0320 (11)	0.0368 (13)	0.0410 (12)	−0.0042 (9)	0.0056 (9)	−0.0123 (10)
C5	0.0460 (13)	0.0482 (15)	0.0509 (14)	−0.0082 (11)	0.0143 (11)	−0.0066 (12)
C6	0.084 (2)	0.0521 (17)	0.0553 (17)	−0.0086 (15)	0.0196 (15)	0.0014 (14)
C7	0.086 (2)	0.062 (2)	0.0620 (19)	0.0063 (17)	−0.0028 (16)	0.0124 (16)
C8	0.0444 (15)	0.083 (2)	0.081 (2)	0.0034 (15)	−0.0087 (14)	0.0110 (18)
C9	0.0341 (12)	0.0646 (18)	0.0640 (17)	−0.0067 (12)	0.0022 (11)	0.0078 (14)
C10	0.0319 (11)	0.0443 (14)	0.0405 (12)	−0.0013 (10)	−0.0032 (9)	−0.0016 (10)
C11	0.0733 (18)	0.0644 (19)	0.0480 (15)	−0.0186 (15)	0.0075 (13)	−0.0012 (14)
C12	0.097 (3)	0.071 (2)	0.071 (2)	−0.029 (2)	0.0016 (18)	0.0202 (18)
C13	0.089 (2)	0.0456 (17)	0.081 (2)	−0.0035 (16)	−0.0157 (18)	−0.0020 (17)
C14	0.0643 (18)	0.0494 (18)	0.079 (2)	0.0019 (14)	0.0018 (15)	−0.0148 (16)
C15	0.0469 (14)	0.0455 (15)	0.0602 (16)	−0.0001 (12)	0.0077 (12)	−0.0128 (13)
C16	0.230 (6)	0.074 (3)	0.057 (2)	−0.036 (3)	−0.013 (3)	0.012 (2)
C17	0.201 (6)	0.072 (3)	0.096 (3)	−0.007 (3)	0.015 (3)	0.013 (3)
C18	0.120 (3)	0.070 (2)	0.105 (3)	0.030 (2)	−0.032 (3)	−0.018 (2)

Geometric parameters (Å, º) top

Co1—N2ⁱ	2.1531 (16)	C6—C7	1.361 (4)
Co1—N2	2.1531 (16)	C6—H6	0.9300
Co1—N4ⁱ	2.165 (2)	C7—C8	1.377 (4)
Co1—N4	2.165 (2)	C7—H7	0.9300
Co1—N3ⁱ	2.180 (2)	C8—C9	1.384 (4)
Co1—N3	2.180 (2)	C8—H8	0.9300
N1—C1	1.343 (3)	C9—H9	0.9300
N1—C3	1.453 (3)	C10—C11	1.375 (3)
N1—H1	0.8600	C10—C15	1.389 (3)
N2—C2	1.345 (3)	C11—C12	1.401 (5)
N2—C1	1.385 (3)	C11—H11	0.9300
N3—C16	1.494 (5)	C12—C13	1.366 (5)
N3—H3A	0.9000	C12—H12	0.9300
N3—H3B	0.9000	C13—C14	1.358 (4)
N4—C18	1.452 (4)	C13—H13	0.9300
N4—H4A	0.9000	C14—C15	1.378 (4)
N4—H4B	0.9000	C14—H14	0.9300
O1—C1	1.237 (3)	C15—H15	0.9300
O2—C2	1.232 (2)	C16—C17	1.498 (6)
C2—C3	1.555 (3)	C16—H16A	0.9700
C3—C10	1.525 (3)	C16—H16B	0.9700
C3—C4	1.529 (3)	C17—C18	1.438 (6)
C4—C9	1.384 (3)	C17—H17A	0.9700
C4—C5	1.387 (3)	C17—H17B	0.9700
C5—C6	1.387 (4)	C18—H18A	0.9700
C5—H5	0.9300	C18—H18B	0.9700

N2ⁱ—Co1—N2	180.00 (10)	C4—C5—H5	119.6
N2ⁱ—Co1—N4ⁱ	90.18 (7)	C7—C6—C5	120.6 (3)
N2—Co1—N4ⁱ	89.82 (7)	C7—C6—H6	119.7
N2ⁱ—Co1—N4	89.82 (7)	C5—C6—H6	119.7
N2—Co1—N4	90.18 (7)	C6—C7—C8	119.6 (3)
N4ⁱ—Co1—N4	180.00 (12)	C6—C7—H7	120.2
N2ⁱ—Co1—N3ⁱ	90.51 (7)	C8—C7—H7	120.2
N2—Co1—N3ⁱ	89.49 (7)	C7—C8—C9	120.0 (3)
N4ⁱ—Co1—N3ⁱ	92.65 (10)	C7—C8—H8	120.0
N4—Co1—N3ⁱ	87.35 (10)	C9—C8—H8	120.0
N2ⁱ—Co1—N3	89.49 (7)	C4—C9—C8	121.2 (3)
N2—Co1—N3	90.51 (7)	C4—C9—H9	119.4
N4ⁱ—Co1—N3	87.35 (10)	C8—C9—H9	119.4
N4—Co1—N3	92.65 (10)	C11—C10—C15	118.3 (2)
N3ⁱ—Co1—N3	180.00 (13)	C11—C10—C3	122.2 (2)
C1—N1—C3	111.68 (16)	C15—C10—C3	119.5 (2)
C1—N1—H1	124.2	C10—C11—C12	120.0 (3)
C3—N1—H1	124.2	C10—C11—H11	120.0
C2—N2—C1	107.61 (17)	C12—C11—H11	120.0
C2—N2—Co1	126.99 (13)	C13—C12—C11	120.2 (3)
C1—N2—Co1	125.27 (14)	C13—C12—H12	119.9
C16—N3—Co1	119.6 (2)	C11—C12—H12	119.9
C16—N3—H3A	107.4	C14—C13—C12	120.4 (3)
Co1—N3—H3A	107.4	C14—C13—H13	119.8
C16—N3—H3B	107.4	C12—C13—H13	119.8
Co1—N3—H3B	107.4	C13—C14—C15	119.9 (3)
H3A—N3—H3B	106.9	C13—C14—H14	120.1
C18—N4—Co1	120.3 (2)	C15—C14—H14	120.1
C18—N4—H4A	107.2	C14—C15—C10	121.2 (3)
Co1—N4—H4A	107.2	C14—C15—H15	119.4
C18—N4—H4B	107.2	C10—C15—H15	119.4
Co1—N4—H4B	107.2	N3—C16—C17	114.6 (3)
H4A—N4—H4B	106.9	N3—C16—H16A	108.6
O1—C1—N1	124.70 (19)	C17—C16—H16A	108.6
O1—C1—N2	123.96 (19)	N3—C16—H16B	108.6
N1—C1—N2	111.35 (19)	C17—C16—H16B	108.6
O2—C2—N2	125.96 (19)	H16A—C16—H16B	107.6
O2—C2—C3	123.48 (19)	C18—C17—C16	117.9 (4)
N2—C2—C3	110.56 (17)	C18—C17—H17A	107.8
N1—C3—C10	113.85 (19)	C16—C17—H17A	107.8
N1—C3—C4	110.53 (17)	C18—C17—H17B	107.8
C10—C3—C4	109.62 (17)	C16—C17—H17B	107.8
N1—C3—C2	98.61 (15)	H17A—C17—H17B	107.2
C10—C3—C2	110.65 (17)	C17—C18—N4	114.5 (4)
C4—C3—C2	113.27 (18)	C17—C18—H18A	108.6
C9—C4—C5	117.8 (2)	N4—C18—H18A	108.6
C9—C4—C3	118.5 (2)	C17—C18—H18B	108.6
C5—C4—C3	123.67 (19)	N4—C18—H18B	108.6
C6—C5—C4	120.7 (2)	H18A—C18—H18B	107.6
C6—C5—H5	119.6

N4ⁱ—Co1—N2—C2	−133.8 (2)	N2—C2—C3—C4	−114.1 (2)
N4—Co1—N2—C2	46.2 (2)	N1—C3—C4—C9	59.8 (3)
N3ⁱ—Co1—N2—C2	−41.2 (2)	C10—C3—C4—C9	−66.5 (3)
N3—Co1—N2—C2	138.8 (2)	C2—C3—C4—C9	169.3 (2)
N4ⁱ—Co1—N2—C1	41.5 (2)	N1—C3—C4—C5	−119.5 (2)
N4—Co1—N2—C1	−138.5 (2)	C10—C3—C4—C5	114.2 (2)
N3ⁱ—Co1—N2—C1	134.1 (2)	C2—C3—C4—C5	−9.9 (3)
N3—Co1—N2—C1	−45.9 (2)	C9—C4—C5—C6	−0.2 (4)
N2ⁱ—Co1—N3—C16	75.1 (2)	C3—C4—C5—C6	179.1 (2)
N2—Co1—N3—C16	−104.9 (2)	C4—C5—C6—C7	0.1 (4)
N4ⁱ—Co1—N3—C16	165.3 (2)	C5—C6—C7—C8	−0.2 (5)
N4—Co1—N3—C16	−14.7 (2)	C6—C7—C8—C9	0.3 (5)
N2ⁱ—Co1—N4—C18	−72.1 (3)	C5—C4—C9—C8	0.4 (4)
N2—Co1—N4—C18	107.9 (3)	C3—C4—C9—C8	−179.0 (3)
N3ⁱ—Co1—N4—C18	−162.7 (3)	C7—C8—C9—C4	−0.5 (5)
N3—Co1—N4—C18	17.3 (3)	N1—C3—C10—C11	−8.7 (3)
C3—N1—C1—O1	−175.7 (3)	C4—C3—C10—C11	115.7 (2)
C3—N1—C1—N2	4.5 (3)	C2—C3—C10—C11	−118.6 (2)
C2—N2—C1—O1	177.8 (3)	N1—C3—C10—C15	173.60 (19)
Co1—N2—C1—O1	1.7 (4)	C4—C3—C10—C15	−62.0 (3)
C2—N2—C1—N1	−2.4 (3)	C2—C3—C10—C15	63.6 (3)
Co1—N2—C1—N1	−178.51 (16)	C15—C10—C11—C12	−1.1 (4)
C1—N2—C2—O2	179.5 (3)	C3—C10—C11—C12	−178.9 (2)
Co1—N2—C2—O2	−4.5 (4)	C10—C11—C12—C13	−0.5 (5)
C1—N2—C2—C3	−0.4 (3)	C11—C12—C13—C14	1.4 (5)
Co1—N2—C2—C3	175.61 (15)	C12—C13—C14—C15	−0.7 (5)
C1—N1—C3—C10	−121.4 (2)	C13—C14—C15—C10	−1.0 (4)
C1—N1—C3—C4	114.7 (2)	C11—C10—C15—C14	1.8 (4)
C1—N1—C3—C2	−4.2 (2)	C3—C10—C15—C14	179.6 (2)
O2—C2—C3—N1	−177.2 (2)	Co1—N3—C16—C17	38.1 (5)
N2—C2—C3—N1	2.7 (2)	N3—C16—C17—C18	−70.4 (6)
O2—C2—C3—C10	−57.6 (3)	C16—C17—C18—N4	74.0 (5)
N2—C2—C3—C10	122.3 (2)	Co1—N4—C18—C17	−44.7 (4)
O2—C2—C3—C4	66.0 (3)

Symmetry code: (i) −x+1, −y+1, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O1	0.90	2.35	3.061 (3)	136
N4—H4B···O2	0.90	2.38	3.095 (3)	137
C5—H5···O2	0.93	2.46	3.089 (3)	125
N1—H1···O1ⁱⁱ	0.86	2.02	2.825 (2)	156
N3—H3B···O2ⁱ	0.90	2.34	3.057 (3)	137
N4—H4A···O1ⁱ	0.90	2.27	2.979 (3)	136
C6—H6···O2ⁱⁱⁱ	0.93	2.39	3.293 (3)	165

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

Experimental details

Crystal data
Chemical formula	[Co(C₁₅H₁₁N₂O₂)₂(C₃H₁₀N₂)₂]
M_r	709.71
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	10.0368 (12), 8.7865 (9), 20.684 (2)
β (°)	102.363 (2)
V (Å³)	1781.8 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.53
Crystal size (mm)	0.50 × 0.46 × 0.45

Data collection
Diffractometer	Siemens SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.777, 0.796
No. of measured, independent and observed [I > 2σ(I)] reflections	8632, 3130, 2536
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.097, 1.05
No. of reflections	3130
No. of parameters	224
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.22

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Co1—N2	2.1531 (16)	Co1—N3	2.180 (2)
Co1—N4	2.165 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O1	0.90	2.35	3.061 (3)	136.2
N4—H4B···O2	0.90	2.38	3.095 (3)	136.6
C5—H5···O2	0.93	2.46	3.089 (3)	125
N1—H1···O1ⁱ	0.86	2.02	2.825 (2)	155.9
N3—H3B···O2ⁱⁱ	0.90	2.34	3.057 (3)	136.5
N4—H4A···O1ⁱⁱ	0.90	2.27	2.979 (3)	135.5
C6—H6···O2ⁱⁱⁱ	0.93	2.39	3.293 (3)	165

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

Acknowledgements

We are grateful for financial support by the Key Project for Fundamental Research of Natural Science Foundation of Jiangsu Lianyungang (CG0806) and the Natural Science Foundation of Huaihai Institute of Technology (2010150019).

References

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