Bis[1,3-bis­(benzimidazol-2-yl)-2-oxa­propane]cobalt(II) dipicrate acetonitrile tris­olvate

Wu, H.; Yun, R.; Huang, X.; Sun, Q.; Qi, B.

doi:10.1107/S1600536809024234

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page m851

doi:10.1107/S1600536809024234

Open

access

Bis[1,3-bis(benzimidazol-2-yl)-2-oxapropane]cobalt(II) dipicrate acetonitrile trisolvate

Huilu Wu,^a ^* Ruirui Yun,^b Xingcai Huang,^a Qingyu Sun ^a and Baoliang Qi ^a

^aSchool of Chemical and Biological Engineering, Lanzhou Jiaotong University, Lanzhou 730070, People's Republic of China, and ^bSchool of Chemical and Biological Engineering, Lanzhou Jiaotong University, Lanzhou 730070, People's Republic of China
^*Correspondence e-mail: wuhuilu@163.com

(Received 11 June 2009; accepted 24 June 2009; online 1 July 2009)

In the title compound, [Co(C₁₆H₁₄N₄O)₂](C₆H₂N₃O₇)₂·3CH₃CN, the Co^II ion is located on a crystallographic twofold rotation axis and is coordinated in a slightly distorted tetrahedral environment by four N atoms from the two bidentate N-heterocycles. The crystal structure is stabilized by intermolecular N—H⋯O and N—H⋯N hydrogen bonds. One of the acetonitrile solvent molecules also lies on a twofold rotation axis.

Related literature

For the crystal structures of related dipicrate metal complexes with 1,3-bis(1-benzyl-1H-benzimidazol-2-yl)-2-oxapropane ligands, see: Wu, Yun, Li, Wang & Huang (2009 ); Wu, Yun, Li, Tao & Wang (2009 ).

Experimental

Crystal data

[Co(C₁₆H₁₄N₄O)₂](C₆H₂N₃O₇)₂·3C₂H₃N
M_r = 1194.93
Monoclinic, P 2/c
a = 11.4114 (3) Å
b = 9.9303 (2) Å
c = 25.1442 (6) Å
β = 111.164 (1)°
V = 2657.12 (11) Å³
Z = 2
Mo Kα radiation
μ = 0.41 mm⁻¹
T = 153 K
0.28 × 0.25 × 0.17 mm

Data collection

Rigaku R-AXIS Spider diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.894, T_max = 0.933
25278 measured reflections
6093 independent reflections
5418 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.031
wR(F²) = 0.087
S = 1.04
6093 reflections
392 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2N⋯O6ⁱ	0.858 (9)	1.893 (12)	2.6746 (14)	150.7 (17)
N2—H2N⋯O5ⁱ	0.858 (9)	2.381 (15)	3.0166 (15)	131.3 (15)
N4—H4N⋯N8	0.858 (9)	2.052 (10)	2.9040 (18)	171.8 (18)
Symmetry code: (i) x, y-1, z.

Data collection: RAPID-AUTO (Rigaku/MSC, 2004 ); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; 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/S1600536809024234/lh2846sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809024234/lh2846Isup2.hkl

checkCIF report

Comment top

The asymmetric unit of the title compound consists of half a discrete di[1,3-bis(benzimidazol-2-yl)-2-oxopropane] cobalt(II) cation, one picrate anion and 1.5 molecules of acetonitrile; the formula unit is generated by a twofold rotation axis. The cation is shown in Fig. 1. The Co^II ion is four-coordinate with a N₄ ligand set. The (1,3-bis(benzimidazol-2-yl)-2-oxopropane) ligand acts as a bidentate donor. The coordination geometry of the Co^II may be best described as slightly distorted tetrahedral. This geometry is assumed by the Co^II to relieve the steric crowding. The crystal structure is stabilized by intermolecular N—H···O and N—H···N hydrogen bonds. Additional stabilization is provided by weak intermolecular C-H···O hydrogen bonds (Fig. 2).

Related literature top

Experimental top

To a stirred solution of 1,3-bis(benzimidazol-2-yl)-2-oxopropane (0.139 g, 0.5 mmol) in hot MeOH (15 ml) was added Co(C₆H₂N₃O₇)₂ (0.129 g, 0.25 mmol) in MeOH (5 ml). A red crystalline product formed rapidly. The precipitate was filtered off, washed with MeOH and absolute Et₂O, and dried in vacuo. The dried precipitate was dissolved in acetonitrile to form a red solution that was allowed to evaporate at room temperature. Red crystals suitable for X-ray diffraction studies were obtained after three days at room temperature. Yield, 0.106 g (66%). (found: C, 50.20; H, 3.51; N,19.94. Calcd. for C50H41N17O16Co: C, 50.26; H, 3.46; N, 19.93)

Computing details top

Data collection: RAPID-AUTO (Rigaku/MSC, 2004); cell refinement: RAPID-AUTO (Rigaku/MSC, 2004); data reduction: RAPID-AUTO (Rigaku/MSC, 2004); 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. Molecular structure and atom numbering for the cation of the title compound. Hydrogen atoms have been omitted for clarity and the displacement ellipsoids are shown at the 30% probability level [symmetry code: (A) -x+1, y, -z+3/2].
	Fig. 2. Part of the crystal structure with hydrogen bonds shown as dashed lines.

Bis[1,3-bis(benzimidazol-2-yl)-2-oxapropane]cobalt(II) dipicrate acetonitrile trisolvate top

Crystal data top

[Co(C₁₆H₁₄N₄O)₂](C₆H₂N₃O₇)₂·3C₂H₃N	F(000) = 1230
M_r = 1194.93	D_x = 1.494 Mg m⁻³
Monoclinic, P2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yc	Cell parameters from 7749 reflections
a = 11.4114 (3) Å	θ = 3.2–27.5°
b = 9.9303 (2) Å	µ = 0.41 mm⁻¹
c = 25.1442 (6) Å	T = 153 K
β = 111.164 (1)°	Block, red
V = 2657.12 (11) Å³	0.28 × 0.25 × 0.17 mm
Z = 2

Data collection top

Rigaku R-AXIS Spider diffractometer	6093 independent reflections
Radiation source: fine-focus sealed tube	5418 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
ϕ and ω scans	θ_max = 27.5°, θ_min = 3.0°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −14→14
T_min = 0.894, T_max = 0.933	k = −12→12
25278 measured reflections	l = −32→32

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)] = 0.031	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.087	w = 1/[σ²(F_o²) + (0.0487P)² + 0.9118P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.001
6093 reflections	Δρ_max = 0.45 e Å⁻³
392 parameters	Δρ_min = −0.30 e Å⁻³
2 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: 0.0036 (5)

Crystal data top

[Co(C₁₆H₁₄N₄O)₂](C₆H₂N₃O₇)₂·3C₂H₃N	V = 2657.12 (11) Å³
M_r = 1194.93	Z = 2
Monoclinic, P2/c	Mo Kα radiation
a = 11.4114 (3) Å	µ = 0.41 mm⁻¹
b = 9.9303 (2) Å	T = 153 K
c = 25.1442 (6) Å	0.28 × 0.25 × 0.17 mm
β = 111.164 (1)°

Data collection top

Rigaku R-AXIS Spider diffractometer	6093 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	5418 reflections with I > 2σ(I)
T_min = 0.894, T_max = 0.933	R_int = 0.021
25278 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	2 restraints
wR(F²) = 0.087	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.45 e Å⁻³
6093 reflections	Δρ_min = −0.30 e Å⁻³
392 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	Occ. (<1)
Co	0.5000	0.36301 (2)	0.7500	0.01700 (8)
O1	0.67337 (8)	0.24981 (9)	0.71220 (4)	0.02259 (19)
O2	0.74591 (13)	0.49084 (15)	0.46620 (6)	0.0583 (4)
O3	0.54824 (12)	0.47322 (11)	0.41556 (5)	0.0409 (3)
O4	0.25535 (11)	0.76959 (16)	0.44436 (6)	0.0567 (4)
O5	0.29928 (11)	0.88294 (12)	0.52194 (5)	0.0428 (3)
O6	0.54003 (9)	0.96666 (10)	0.56756 (4)	0.0292 (2)
O7	0.78254 (12)	0.91568 (16)	0.63960 (5)	0.0522 (3)
O8	0.88585 (11)	0.89860 (13)	0.58266 (5)	0.0420 (3)
N1	0.41234 (10)	0.25020 (10)	0.67914 (4)	0.0200 (2)
N2	0.39034 (10)	0.10735 (11)	0.60795 (4)	0.0202 (2)
N3	0.62918 (10)	0.49981 (11)	0.74562 (4)	0.0195 (2)
N4	0.77113 (11)	0.58828 (12)	0.71442 (5)	0.0260 (2)
N5	0.63674 (13)	0.52737 (13)	0.45326 (5)	0.0342 (3)
N6	0.33090 (11)	0.81256 (13)	0.48951 (5)	0.0309 (3)
N7	0.79113 (12)	0.88240 (13)	0.59422 (5)	0.0332 (3)
N8	0.93174 (15)	0.59702 (16)	0.64743 (6)	0.0452 (4)
N9	1.0000	0.3626 (2)	0.7500	0.0471 (5)
C1	0.28403 (12)	0.23999 (12)	0.64561 (5)	0.0196 (2)
C2	0.17845 (12)	0.29913 (14)	0.65151 (5)	0.0252 (3)
H2	0.1860	0.3604	0.6816	0.030*
C3	0.06220 (13)	0.26482 (15)	0.61173 (6)	0.0282 (3)
H3	−0.0113	0.3029	0.6150	0.034*
C4	0.04975 (13)	0.17528 (15)	0.56674 (6)	0.0278 (3)
H4	−0.0317	0.1546	0.5402	0.033*
C5	0.15352 (13)	0.11673 (14)	0.56030 (6)	0.0249 (3)
H5	0.1458	0.0568	0.5298	0.030*
C6	0.26998 (12)	0.14996 (12)	0.60080 (5)	0.0194 (2)
C7	0.47004 (12)	0.16761 (12)	0.65481 (5)	0.0197 (2)
C8	0.60830 (12)	0.13872 (13)	0.67854 (6)	0.0252 (3)
H8A	0.6244	0.0564	0.7023	0.030*
H8B	0.6391	0.1231	0.6469	0.030*
C9	0.68619 (12)	0.35957 (13)	0.67806 (5)	0.0222 (3)
H9A	0.6121	0.3650	0.6422	0.027*
H9B	0.7624	0.3481	0.6684	0.027*
C10	0.69630 (11)	0.48306 (13)	0.71274 (5)	0.0201 (2)
C11	0.75372 (13)	0.68185 (14)	0.75169 (6)	0.0267 (3)
C12	0.80865 (17)	0.80687 (16)	0.77019 (7)	0.0396 (4)
H12	0.8685	0.8446	0.7562	0.047*
C13	0.77203 (19)	0.87304 (16)	0.80967 (8)	0.0450 (4)
H13	0.8071	0.9588	0.8232	0.054*
C14	0.68394 (17)	0.81668 (16)	0.83043 (7)	0.0393 (4)
H14	0.6612	0.8653	0.8578	0.047*
C15	0.62941 (14)	0.69269 (15)	0.81217 (6)	0.0293 (3)
H15	0.5702	0.6549	0.8265	0.035*
C16	0.66544 (13)	0.62542 (13)	0.77169 (5)	0.0221 (3)
C17	0.61070 (14)	0.63884 (13)	0.48431 (6)	0.0262 (3)
C18	0.48772 (13)	0.67268 (13)	0.47497 (5)	0.0238 (3)
H18	0.4208	0.6222	0.4489	0.029*
C19	0.46257 (13)	0.78010 (13)	0.50371 (5)	0.0233 (3)
C20	0.55850 (13)	0.86220 (13)	0.54417 (5)	0.0228 (3)
C21	0.68386 (13)	0.81456 (14)	0.55233 (6)	0.0260 (3)
C22	0.70968 (14)	0.71058 (15)	0.52261 (6)	0.0288 (3)
H22	0.7941	0.6878	0.5281	0.035*
C23	1.05744 (17)	0.6226 (2)	0.58074 (8)	0.0495 (5)
H23A	1.0127	0.5755	0.5449	0.059*
H23B	1.1415	0.5837	0.5987	0.059*
H23C	1.0648	0.7183	0.5730	0.059*
C24	0.98832 (15)	0.60810 (18)	0.61876 (7)	0.0371 (4)
C25	1.0000	0.1051 (3)	0.7500	0.0971 (16)
H25A	1.0691	0.0722	0.7836	0.116*	0.50
H25B	1.0110	0.0722	0.7154	0.116*	0.50
H25C	0.9199	0.0722	0.7511	0.116*	0.50
C26	1.0000	0.2497 (2)	0.7500	0.0355 (5)
H2N	0.4130 (16)	0.0525 (15)	0.5871 (7)	0.037 (5)*
H4N	0.8242 (14)	0.5947 (19)	0.6975 (7)	0.041 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co	0.01758 (12)	0.01751 (13)	0.01522 (12)	0.000	0.00511 (9)	0.000
O1	0.0227 (5)	0.0215 (4)	0.0208 (4)	−0.0016 (3)	0.0046 (4)	−0.0025 (3)
O2	0.0533 (8)	0.0616 (9)	0.0637 (8)	0.0260 (7)	0.0257 (7)	−0.0152 (7)
O3	0.0612 (8)	0.0328 (6)	0.0310 (5)	0.0086 (5)	0.0194 (5)	−0.0069 (5)
O4	0.0274 (6)	0.0785 (10)	0.0554 (8)	−0.0016 (6)	0.0044 (6)	−0.0380 (7)
O5	0.0291 (6)	0.0489 (7)	0.0506 (7)	0.0037 (5)	0.0147 (5)	−0.0249 (6)
O6	0.0275 (5)	0.0275 (5)	0.0321 (5)	0.0021 (4)	0.0102 (4)	−0.0101 (4)
O7	0.0354 (6)	0.0790 (10)	0.0353 (6)	0.0055 (6)	0.0046 (5)	−0.0223 (6)
O8	0.0292 (6)	0.0469 (7)	0.0486 (7)	−0.0026 (5)	0.0126 (5)	0.0015 (5)
N1	0.0186 (5)	0.0204 (5)	0.0200 (5)	0.0016 (4)	0.0058 (4)	−0.0023 (4)
N2	0.0214 (5)	0.0189 (5)	0.0203 (5)	0.0001 (4)	0.0075 (4)	−0.0037 (4)
N3	0.0211 (5)	0.0207 (5)	0.0178 (5)	−0.0001 (4)	0.0082 (4)	−0.0005 (4)
N4	0.0287 (6)	0.0261 (6)	0.0286 (6)	−0.0045 (5)	0.0170 (5)	−0.0010 (5)
N5	0.0495 (8)	0.0292 (6)	0.0304 (6)	0.0138 (6)	0.0222 (6)	0.0023 (5)
N6	0.0251 (6)	0.0324 (6)	0.0345 (6)	0.0000 (5)	0.0100 (5)	−0.0109 (5)
N7	0.0271 (6)	0.0361 (7)	0.0327 (6)	0.0065 (5)	0.0061 (5)	−0.0024 (5)
N8	0.0477 (9)	0.0524 (9)	0.0459 (8)	0.0125 (7)	0.0295 (7)	0.0123 (7)
N9	0.0421 (12)	0.0387 (12)	0.0568 (13)	0.000	0.0132 (10)	0.000
C1	0.0192 (6)	0.0204 (6)	0.0178 (5)	−0.0006 (5)	0.0052 (5)	−0.0001 (4)
C2	0.0217 (6)	0.0300 (7)	0.0234 (6)	0.0023 (5)	0.0074 (5)	−0.0052 (5)
C3	0.0199 (6)	0.0351 (7)	0.0289 (7)	0.0021 (5)	0.0080 (5)	−0.0046 (6)
C4	0.0203 (6)	0.0330 (7)	0.0259 (6)	−0.0026 (5)	0.0035 (5)	−0.0040 (6)
C5	0.0247 (7)	0.0264 (6)	0.0215 (6)	−0.0022 (5)	0.0059 (5)	−0.0051 (5)
C6	0.0204 (6)	0.0191 (6)	0.0196 (5)	−0.0003 (4)	0.0082 (5)	0.0008 (4)
C7	0.0212 (6)	0.0167 (5)	0.0209 (6)	−0.0001 (5)	0.0073 (5)	−0.0009 (4)
C8	0.0206 (6)	0.0220 (6)	0.0294 (6)	0.0019 (5)	0.0049 (5)	−0.0078 (5)
C9	0.0217 (6)	0.0264 (7)	0.0198 (6)	0.0004 (5)	0.0091 (5)	−0.0015 (5)
C10	0.0189 (6)	0.0239 (6)	0.0179 (5)	0.0011 (5)	0.0073 (5)	0.0026 (5)
C11	0.0299 (7)	0.0246 (7)	0.0280 (6)	−0.0030 (5)	0.0133 (6)	−0.0004 (5)
C12	0.0469 (9)	0.0293 (8)	0.0490 (9)	−0.0132 (7)	0.0251 (8)	−0.0049 (7)
C13	0.0582 (11)	0.0270 (8)	0.0540 (10)	−0.0149 (7)	0.0254 (9)	−0.0139 (7)
C14	0.0509 (10)	0.0305 (8)	0.0415 (8)	−0.0047 (7)	0.0228 (8)	−0.0134 (7)
C15	0.0347 (8)	0.0284 (7)	0.0283 (6)	−0.0023 (6)	0.0156 (6)	−0.0056 (6)
C16	0.0240 (6)	0.0213 (6)	0.0211 (6)	−0.0010 (5)	0.0080 (5)	−0.0001 (5)
C17	0.0380 (8)	0.0225 (6)	0.0229 (6)	0.0085 (5)	0.0168 (6)	0.0030 (5)
C18	0.0335 (7)	0.0202 (6)	0.0203 (6)	0.0012 (5)	0.0130 (5)	0.0008 (5)
C19	0.0259 (7)	0.0229 (6)	0.0229 (6)	0.0037 (5)	0.0111 (5)	−0.0006 (5)
C20	0.0256 (7)	0.0230 (6)	0.0216 (6)	0.0032 (5)	0.0106 (5)	0.0002 (5)
C21	0.0252 (7)	0.0282 (7)	0.0238 (6)	0.0038 (5)	0.0081 (5)	0.0003 (5)
C22	0.0287 (7)	0.0332 (7)	0.0269 (6)	0.0109 (6)	0.0129 (6)	0.0036 (6)
C23	0.0350 (9)	0.0802 (14)	0.0412 (9)	0.0146 (9)	0.0233 (8)	0.0109 (9)
C24	0.0319 (8)	0.0471 (9)	0.0344 (8)	0.0142 (7)	0.0146 (7)	0.0100 (7)
C25	0.109 (3)	0.0309 (15)	0.110 (3)	0.000	−0.011 (3)	0.000
C26	0.0263 (10)	0.0338 (12)	0.0407 (11)	0.000	0.0052 (9)	0.000

Geometric parameters (Å, º) top

Co—N1	2.0355 (10)	C4—H4	0.9500
Co—N1ⁱ	2.0355 (10)	C5—C6	1.3910 (18)
Co—N3	2.0367 (11)	C5—H5	0.9500
Co—N3ⁱ	2.0367 (11)	C7—C8	1.4993 (18)
O1—C8	1.4250 (15)	C8—H8A	0.9900
O1—C9	1.4272 (16)	C8—H8B	0.9900
O2—N5	1.2234 (19)	C9—C10	1.4849 (18)
O3—N5	1.2315 (18)	C9—H9A	0.9900
O4—N6	1.2278 (17)	C9—H9B	0.9900
O5—N6	1.2233 (16)	C11—C12	1.393 (2)
O6—C20	1.2475 (16)	C11—C16	1.3956 (19)
O7—N7	1.2255 (17)	C12—C13	1.375 (2)
O8—N7	1.2270 (17)	C12—H12	0.9500
N1—C7	1.3308 (16)	C13—C14	1.405 (3)
N1—C1	1.4048 (16)	C13—H13	0.9500
N2—C7	1.3416 (16)	C14—C15	1.381 (2)
N2—C6	1.3855 (16)	C14—H14	0.9500
N2—H2N	0.858 (9)	C15—C16	1.3977 (19)
N3—C10	1.3247 (15)	C15—H15	0.9500
N3—C16	1.4004 (16)	C17—C18	1.378 (2)
N4—C10	1.3404 (17)	C17—C22	1.388 (2)
N4—C11	1.3840 (18)	C18—C19	1.3756 (18)
N4—H4N	0.858 (9)	C18—H18	0.9500
N5—C17	1.4459 (17)	C19—C20	1.4469 (19)
N6—C19	1.4497 (18)	C20—C21	1.4492 (19)
N7—C21	1.4597 (19)	C21—C22	1.368 (2)
N8—C24	1.133 (2)	C22—H22	0.9500
N9—C26	1.121 (3)	C23—C24	1.450 (2)
C1—C2	1.3956 (18)	C23—H23A	0.9800
C1—C6	1.4013 (17)	C23—H23B	0.9800
C2—C3	1.3850 (19)	C23—H23C	0.9800
C2—H2	0.9500	C25—C26	1.436 (4)
C3—C4	1.405 (2)	C25—H25A	0.9800
C3—H3	0.9500	C25—H25B	0.9800
C4—C5	1.380 (2)	C25—H25C	0.9800

N1—Co—N1ⁱ	113.22 (6)	C10—C9—H9A	110.5
N1—Co—N3	117.15 (4)	O1—C9—H9B	110.5
N1ⁱ—Co—N3	106.14 (4)	C10—C9—H9B	110.5
N1—Co—N3ⁱ	106.13 (4)	H9A—C9—H9B	108.7
N1ⁱ—Co—N3ⁱ	117.15 (4)	N3—C10—N4	112.81 (11)
N3—Co—N3ⁱ	96.33 (6)	N3—C10—C9	122.03 (11)
C8—O1—C9	112.25 (10)	N4—C10—C9	125.15 (11)
C7—N1—C1	105.13 (10)	N4—C11—C12	131.85 (13)
C7—N1—Co	124.97 (9)	N4—C11—C16	105.85 (12)
C1—N1—Co	129.90 (8)	C12—C11—C16	122.27 (13)
C7—N2—C6	107.67 (10)	C13—C12—C11	116.71 (15)
C7—N2—H2N	124.2 (12)	C13—C12—H12	121.6
C6—N2—H2N	128.2 (12)	C11—C12—H12	121.6
C10—N3—C16	105.33 (10)	C12—C13—C14	121.49 (14)
C10—N3—Co	122.88 (9)	C12—C13—H13	119.3
C16—N3—Co	131.77 (8)	C14—C13—H13	119.3
C10—N4—C11	107.41 (11)	C15—C14—C13	121.90 (14)
C10—N4—H4N	126.7 (13)	C15—C14—H14	119.0
C11—N4—H4N	125.8 (13)	C13—C14—H14	119.0
O2—N5—O3	123.27 (13)	C14—C15—C16	116.89 (14)
O2—N5—C17	118.13 (14)	C14—C15—H15	121.6
O3—N5—C17	118.60 (13)	C16—C15—H15	121.6
O5—N6—O4	122.50 (13)	C11—C16—C15	120.73 (13)
O5—N6—C19	119.46 (12)	C11—C16—N3	108.58 (11)
O4—N6—C19	118.03 (12)	C15—C16—N3	130.67 (12)
O7—N7—O8	123.97 (14)	C18—C17—C22	121.11 (12)
O7—N7—C21	117.91 (13)	C18—C17—N5	119.33 (13)
O8—N7—C21	118.07 (12)	C22—C17—N5	119.56 (13)
C2—C1—C6	120.09 (12)	C19—C18—C17	119.49 (13)
C2—C1—N1	131.19 (11)	C19—C18—H18	120.3
C6—C1—N1	108.69 (11)	C17—C18—H18	120.3
C3—C2—C1	117.27 (12)	C18—C19—C20	123.90 (12)
C3—C2—H2	121.4	C18—C19—N6	115.93 (12)
C1—C2—H2	121.4	C20—C19—N6	120.12 (11)
C2—C3—C4	121.95 (13)	O6—C20—C19	125.89 (12)
C2—C3—H3	119.0	O6—C20—C21	122.06 (13)
C4—C3—H3	119.0	C19—C20—C21	111.92 (11)
C5—C4—C3	121.29 (12)	C22—C21—C20	124.43 (13)
C5—C4—H4	119.4	C22—C21—N7	116.92 (13)
C3—C4—H4	119.4	C20—C21—N7	118.64 (12)
C4—C5—C6	116.58 (12)	C21—C22—C17	119.00 (13)
C4—C5—H5	121.7	C21—C22—H22	120.5
C6—C5—H5	121.7	C17—C22—H22	120.5
N2—C6—C5	131.51 (12)	C24—C23—H23A	109.5
N2—C6—C1	105.68 (11)	C24—C23—H23B	109.5
C5—C6—C1	122.80 (12)	H23A—C23—H23B	109.5
N1—C7—N2	112.80 (11)	C24—C23—H23C	109.5
N1—C7—C8	124.00 (11)	H23A—C23—H23C	109.5
N2—C7—C8	123.12 (11)	H23B—C23—H23C	109.5
O1—C8—C7	109.64 (10)	N8—C24—C23	178.40 (18)
O1—C8—H8A	109.7	C26—C25—H25A	109.5
C7—C8—H8A	109.7	C26—C25—H25B	109.5
O1—C8—H8B	109.7	H25A—C25—H25B	109.5
C7—C8—H8B	109.7	C26—C25—H25C	109.5
H8A—C8—H8B	108.2	H25A—C25—H25C	109.5
O1—C9—C10	106.29 (10)	H25B—C25—H25C	109.5
O1—C9—H9A	110.5	N9—C26—C25	180.000 (3)

N1ⁱ—Co—N1—C7	−63.92 (10)	O1—C9—C10—N4	141.87 (12)
N3—Co—N1—C7	60.12 (11)	C10—N4—C11—C12	178.52 (17)
N3ⁱ—Co—N1—C7	166.22 (10)	C10—N4—C11—C16	0.22 (15)
N1ⁱ—Co—N1—C1	116.01 (11)	N4—C11—C12—C13	−177.85 (17)
N3—Co—N1—C1	−119.95 (10)	C16—C11—C12—C13	0.2 (3)
N3ⁱ—Co—N1—C1	−13.86 (11)	C11—C12—C13—C14	0.3 (3)
N1—Co—N3—C10	−29.43 (11)	C12—C13—C14—C15	−0.3 (3)
N1ⁱ—Co—N3—C10	98.12 (10)	C13—C14—C15—C16	−0.3 (3)
N3ⁱ—Co—N3—C10	−141.21 (11)	N4—C11—C16—C15	177.74 (13)
N1—Co—N3—C16	148.33 (10)	C12—C11—C16—C15	−0.8 (2)
N1ⁱ—Co—N3—C16	−84.11 (11)	N4—C11—C16—N3	−0.97 (15)
N3ⁱ—Co—N3—C16	36.55 (10)	C12—C11—C16—N3	−179.47 (14)
C7—N1—C1—C2	177.34 (14)	C14—C15—C16—C11	0.8 (2)
Co—N1—C1—C2	−2.6 (2)	C14—C15—C16—N3	179.14 (14)
C7—N1—C1—C6	−0.67 (13)	C10—N3—C16—C11	1.34 (14)
Co—N1—C1—C6	179.40 (8)	Co—N3—C16—C11	−176.71 (9)
C6—C1—C2—C3	0.0 (2)	C10—N3—C16—C15	−177.19 (14)
N1—C1—C2—C3	−177.80 (13)	Co—N3—C16—C15	4.8 (2)
C1—C2—C3—C4	−0.6 (2)	O2—N5—C17—C18	−172.99 (14)
C2—C3—C4—C5	0.3 (2)	O3—N5—C17—C18	6.38 (19)
C3—C4—C5—C6	0.6 (2)	O2—N5—C17—C22	7.5 (2)
C7—N2—C6—C5	−178.36 (14)	O3—N5—C17—C22	−173.11 (13)
C7—N2—C6—C1	0.86 (14)	C22—C17—C18—C19	0.6 (2)
C4—C5—C6—N2	177.88 (13)	N5—C17—C18—C19	−178.90 (12)
C4—C5—C6—C1	−1.2 (2)	C17—C18—C19—C20	−0.1 (2)
C2—C1—C6—N2	−178.38 (12)	C17—C18—C19—N6	177.32 (12)
N1—C1—C6—N2	−0.12 (13)	O5—N6—C19—C18	162.30 (14)
C2—C1—C6—C5	0.92 (19)	O4—N6—C19—C18	−19.0 (2)
N1—C1—C6—C5	179.19 (12)	O5—N6—C19—C20	−20.2 (2)
C1—N1—C7—N2	1.27 (14)	O4—N6—C19—C20	158.52 (15)
Co—N1—C7—N2	−178.79 (8)	C18—C19—C20—O6	173.77 (13)
C1—N1—C7—C8	−175.73 (12)	N6—C19—C20—O6	−3.5 (2)
Co—N1—C7—C8	4.21 (18)	C18—C19—C20—C21	−2.18 (18)
C6—N2—C7—N1	−1.38 (15)	N6—C19—C20—C21	−179.48 (12)
C6—N2—C7—C8	175.65 (12)	O6—C20—C21—C22	−171.77 (14)
C9—O1—C8—C7	−77.34 (13)	C19—C20—C21—C22	4.36 (19)
N1—C7—C8—O1	−26.34 (18)	O6—C20—C21—N7	7.1 (2)
N2—C7—C8—O1	156.97 (11)	C19—C20—C21—N7	−176.76 (12)
C8—O1—C9—C10	153.52 (10)	O7—N7—C21—C22	−140.26 (15)
C16—N3—C10—N4	−1.25 (14)	O8—N7—C21—C22	37.34 (19)
Co—N3—C10—N4	177.02 (8)	O7—N7—C21—C20	40.78 (19)
C16—N3—C10—C9	179.16 (11)	O8—N7—C21—C20	−141.62 (13)
Co—N3—C10—C9	−2.57 (16)	C20—C21—C22—C17	−4.2 (2)
C11—N4—C10—N3	0.67 (15)	N7—C21—C22—C17	176.93 (12)
C11—N4—C10—C9	−179.76 (12)	C18—C17—C22—C21	1.5 (2)
O1—C9—C10—N3	−38.59 (16)	N5—C17—C22—C21	−179.07 (12)

Symmetry code: (i) −x+1, y, −z+3/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O6ⁱⁱ	0.86 (1)	1.89 (1)	2.6746 (14)	151 (2)
N2—H2N···O5ⁱⁱ	0.86 (1)	2.38 (2)	3.0166 (15)	131 (2)
N4—H4N···N8	0.86 (1)	2.05 (1)	2.9040 (18)	172 (2)

Symmetry code: (ii) x, y−1, z.

Experimental details

Crystal data
Chemical formula	[Co(C₁₆H₁₄N₄O)₂](C₆H₂N₃O₇)₂·3C₂H₃N
M_r	1194.93
Crystal system, space group	Monoclinic, P2/c
Temperature (K)	153
a, b, c (Å)	11.4114 (3), 9.9303 (2), 25.1442 (6)
β (°)	111.164 (1)
V (Å³)	2657.12 (11)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.41
Crystal size (mm)	0.28 × 0.25 × 0.17

Data collection
Diffractometer	Rigaku R-AXIS Spider diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.894, 0.933
No. of measured, independent and observed [I > 2σ(I)] reflections	25278, 6093, 5418
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.087, 1.04
No. of reflections	6093
No. of parameters	392
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.30

Computer programs: RAPID-AUTO (Rigaku/MSC, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O6ⁱ	0.858 (9)	1.893 (12)	2.6746 (14)	150.7 (17)
N2—H2N···O5ⁱ	0.858 (9)	2.381 (15)	3.0166 (15)	131.3 (15)
N4—H4N···N8	0.858 (9)	2.052 (10)	2.9040 (18)	171.8 (18)

Symmetry code: (i) x, y−1, z.

Acknowledgements

The authors acknowledge financial support and a grant from the `Qing Lan' Talent Engineering Funds and the Students' Science and Technology Innovation Funds (grant No. DXS2008–040,041) of Lanzhou Jiaotong University. A grant from `Long Yuan Qing Nian' of Gansu Province is also acknowledged.

References

Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku/MSC (2004). RAPID-AUTO. Rigaku/MSC, The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wu, H., Yun, R., Li, K., Tao, S. & Wang, K. (2009). Acta Cryst. E65, m786. Web of Science CSD CrossRef IUCr Journals Google Scholar
Wu, H., Yun, R., Li, K., Wang, K. & Huang, X. (2009). Acta Cryst. E65, m751–m752. Web of Science CSD CrossRef CAS 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.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page m851

doi:10.1107/S1600536809024234

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Bis[1,3-bis­­(benzimidazol-2-yl)-2-oxa­propane]cobalt(II) dipicrate aceto­nitrile tris­­olvate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Bis[1,3-bis(benzimidazol-2-yl)-2-oxapropane]cobalt(II) dipicrate acetonitrile trisolvate