Aqua-[2,2'-(propane-1,3-di-yl)bis-(5-car-boxy-1H-imidazole-4-carboxyl-ato)-κ(4)N(3),O(4):N(3'),O(4')](pyridine-κN)cobalt(II)-4,4'-bipyridine (1/1).

In the title compound, [Co(C(13)H(10)N(4)O(8))(C(5)H(5)N)(H(2)O)]·C(10)H(8)N(2), the asymmetric unit comprises half a Co(II) complex located on a mirror plane and half a cocrystallized mol-ecule of 4,4'-bipyridine located on an inversion center. The Co(II) ion is six coordinate, with distorted octa-hedral geometry, ligated by two N atoms and two O atoms from a 2,2'-(propane-1,3-di-yl)bis-(5-carboxy-1H-imidazole-4-carboxyl-ate) dianion, one N atom from a pyridine mol-ecule and one coordinating water mol-ecule. The Co-O bond lengths range from 2.076 (2) to 2.1441 (15) Å, while the Co-N bond lengths are 2.138 (3) and 2.1515 (17) Å. A two-dimensional network of N-H⋯O and O-H⋯N hydrogen bonds stabilizes the crystal packing. There are π-π inter-actions between the bipyridine and imidazole rings [centroid-centroid distance = 3.7694 (4) Å]. The propane-1,3-diyl group is disordered over two conformations, with refined occupancies of 0.755 (8) and 0.245 (8).

Related literature

For complexes based on substituted 4,5-imidazole­dicarb­oxy­lic acids, see: Zhu et al. (2010 ▶, 2011 ▶); Lu et al. (2010 ▶); Song et al. (2010 ▶); Zhang et al. (2010 ▶); Wang et al. (2008 ▶); Feng et al. (2010 ▶); Liu et al. (2010 ▶); Zheng et al. (2011 ▶); Li et al. (2009 ▶, 2010 ▶).

Experimental

Crystal data

[Co(C13H10N4O8)(C5H5N)(H2O)]·C10H8N2

M = 661.47

Monoclinic,

a = 7.9733 (10) Å

b = 20.738 (3) Å

c = 8.2987 (11) Å

β = 91.350 (2)°

V = 1371.8 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.70 mm−1

T = 296 K

0.22 × 0.18 × 0.11 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ▶) T min = 0.862, T max = 0.927

11480 measured reflections

3443 independent reflections

2633 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.105

S = 1.05

3443 reflections

219 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.43 e Å−3

Δρmin = −0.34 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); 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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812029856/pk2422sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812029856/pk2422Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Co(C13H10N4O8)(C5H5N)(H2O)]·C10H8N2	F(000) = 680
Mr = 661.47	Dx = 1.601 Mg m−3
Monoclinic, P21/m	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yb	Cell parameters from 2701 reflections
a = 7.9733 (10) Å	θ = 2.6–28.3°
b = 20.738 (3) Å	µ = 0.70 mm−1
c = 8.2987 (11) Å	T = 296 K
β = 91.350 (2)°	Prismatic, red
V = 1371.8 (3) Å3	0.22 × 0.18 × 0.11 mm
Z = 2

Bruker SMART CCD area-detector diffractometer	3443 independent reflections
Radiation source: fine-focus sealed tube	2633 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
φ and ω scans	θmax = 28.3°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −10→10
Tmin = 0.862, Tmax = 0.927	k = −27→27
11480 measured reflections	l = −11→10

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) = 0.105	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0442P)2 + 0.5516P] where P = (Fo2 + 2Fc2)/3
3443 reflections	(Δ/σ)max < 0.001
219 parameters	Δρmax = 0.43 e Å−3
1 restraint	Δρmin = −0.34 e Å−3

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
Co1	1.06603 (5)	0.2500	0.45178 (5)	0.03122 (13)
O1	1.1510 (2)	0.32701 (7)	0.60553 (18)	0.0383 (4)
O2	1.2252 (2)	0.43073 (8)	0.6011 (2)	0.0522 (5)
O3	1.2037 (3)	0.52310 (8)	0.4133 (2)	0.0529 (5)
H3	1.2128	0.4918	0.4734	0.079*
O4	1.1130 (3)	0.54174 (8)	0.1645 (2)	0.0529 (5)
O5	1.3034 (3)	0.2500	0.3543 (3)	0.0427 (6)
H1W	1.3294	0.2130	0.3301	0.064*	0.50
N1	1.0110 (2)	0.33325 (8)	0.3051 (2)	0.0333 (4)
N2	0.9918 (2)	0.41425 (8)	0.1356 (2)	0.0376 (4)
H2	0.9680	0.4358	0.0494	0.045*
N3	0.8291 (3)	0.2500	0.5671 (3)	0.0362 (6)
N4	0.5482 (3)	0.64535 (11)	0.7813 (3)	0.0581 (6)
C1	1.0812 (3)	0.38718 (10)	0.3751 (3)	0.0323 (5)
C2	1.0707 (3)	0.43808 (10)	0.2707 (3)	0.0339 (5)
C3	0.9574 (3)	0.35140 (10)	0.1597 (3)	0.0391 (5)
C4	1.1577 (3)	0.38108 (10)	0.5396 (3)	0.0352 (5)
C5	1.1307 (3)	0.50565 (11)	0.2790 (3)	0.0389 (5)
C6	0.8845 (10)	0.3117 (3)	0.0277 (8)	0.077 (2)	0.755 (8)
H6A	0.9736	0.2990	−0.0432	0.092*	0.755 (8)
H6B	0.8060	0.3380	−0.0347	0.092*	0.755 (8)
C7	0.7919 (6)	0.2500	0.0846 (6)	0.0417 (13)	0.755 (8)
H7A	0.6779	0.2500	0.0411	0.050*	0.755 (8)
H7B	0.7867	0.2500	0.2012	0.050*	0.755 (8)
C8	0.7494 (3)	0.30506 (12)	0.6012 (3)	0.0432 (6)
H8	0.8032	0.3439	0.5807	0.052*
C9	0.5915 (3)	0.30676 (14)	0.6651 (3)	0.0531 (7)
H9	0.5404	0.3460	0.6869	0.064*
C10	0.5108 (5)	0.2500	0.6959 (5)	0.0564 (10)
H10	0.4033	0.2500	0.7371	0.068*
C11	0.6117 (4)	0.63819 (13)	0.9295 (4)	0.0565 (7)
H11	0.6701	0.6727	0.9751	0.068*
C12	0.5967 (3)	0.58259 (12)	1.0209 (3)	0.0467 (6)
H12	0.6442	0.5802	1.1241	0.056*
C13	0.5101 (3)	0.53088 (11)	0.9558 (3)	0.0378 (5)
C14	0.4429 (4)	0.53878 (13)	0.8010 (4)	0.0604 (8)
H14	0.3829	0.5054	0.7520	0.072*
C15	0.4649 (4)	0.59541 (15)	0.7211 (4)	0.0681 (9)
H15	0.4183	0.5992	0.6177	0.082*
C7'	0.9726 (4)	0.25000 (15)	−0.0032 (4)	0.048 (4)*	0.245 (8)
H7'1	0.9962	0.2500	−0.1173	0.057*	0.245 (8)
H7'2	1.0762	0.2500	0.0604	0.057*	0.245 (8)
C6'	0.841 (2)	0.3086 (7)	0.049 (2)	0.034 (3)*	0.245 (8)
H6'1	0.8001	0.3323	−0.0446	0.041*	0.245 (8)
H6'2	0.7470	0.2917	0.1074	0.041*	0.245 (8)

	U11	U22	U33	U12	U13	U23
Co1	0.0391 (2)	0.0229 (2)	0.0313 (2)	0.000	−0.00719 (16)	0.000
O1	0.0514 (10)	0.0286 (8)	0.0344 (9)	−0.0005 (7)	−0.0105 (7)	−0.0007 (7)
O2	0.0784 (13)	0.0338 (9)	0.0434 (10)	−0.0142 (8)	−0.0229 (9)	−0.0026 (7)
O3	0.0842 (14)	0.0277 (9)	0.0458 (11)	−0.0100 (8)	−0.0171 (9)	−0.0005 (7)
O4	0.0819 (13)	0.0294 (9)	0.0466 (11)	−0.0079 (8)	−0.0133 (9)	0.0070 (8)
O5	0.0451 (13)	0.0284 (11)	0.0549 (15)	0.000	0.0038 (11)	0.000
N1	0.0417 (10)	0.0235 (8)	0.0342 (10)	−0.0004 (7)	−0.0091 (8)	−0.0011 (7)
N2	0.0518 (11)	0.0257 (9)	0.0349 (10)	−0.0025 (8)	−0.0109 (8)	0.0041 (8)
N3	0.0409 (15)	0.0319 (14)	0.0356 (15)	0.000	−0.0052 (11)	0.000
N4	0.0629 (15)	0.0422 (13)	0.0696 (17)	0.0037 (11)	0.0090 (12)	0.0145 (11)
C1	0.0381 (11)	0.0237 (10)	0.0349 (12)	0.0008 (9)	−0.0056 (9)	−0.0030 (8)
C2	0.0414 (12)	0.0268 (10)	0.0333 (12)	0.0016 (9)	−0.0040 (9)	−0.0017 (9)
C3	0.0533 (14)	0.0280 (11)	0.0354 (13)	−0.0024 (10)	−0.0111 (10)	0.0007 (9)
C4	0.0427 (12)	0.0288 (11)	0.0336 (12)	0.0000 (9)	−0.0074 (9)	−0.0031 (9)
C5	0.0497 (14)	0.0275 (11)	0.0394 (13)	−0.0007 (10)	−0.0042 (10)	−0.0029 (10)
C6	0.127 (6)	0.053 (3)	0.049 (3)	−0.053 (3)	−0.024 (4)	0.005 (2)
C7	0.049 (3)	0.033 (2)	0.042 (3)	0.000	−0.020 (2)	0.000
C8	0.0486 (14)	0.0405 (13)	0.0402 (14)	0.0048 (11)	−0.0044 (10)	0.0007 (11)
C9	0.0528 (16)	0.0609 (18)	0.0456 (15)	0.0178 (13)	−0.0006 (12)	0.0010 (13)
C10	0.043 (2)	0.084 (3)	0.042 (2)	0.000	−0.0003 (16)	0.000
C11	0.0655 (18)	0.0355 (14)	0.069 (2)	−0.0091 (12)	0.0129 (15)	−0.0069 (13)
C12	0.0578 (16)	0.0388 (13)	0.0433 (14)	−0.0068 (11)	0.0000 (11)	−0.0039 (11)
C13	0.0384 (12)	0.0330 (12)	0.0419 (13)	−0.0018 (9)	−0.0019 (10)	0.0015 (10)
C14	0.076 (2)	0.0456 (15)	0.0580 (18)	−0.0175 (14)	−0.0252 (15)	0.0147 (13)
C15	0.083 (2)	0.0592 (19)	0.061 (2)	−0.0065 (16)	−0.0203 (16)	0.0207 (16)

Co1—O5	2.076 (2)	C6—H6A	0.9700
Co1—N3	2.138 (3)	C6—H6B	0.9700
Co1—O1	2.1441 (15)	C7—C6i	1.557 (6)
Co1—O1i	2.1441 (15)	C7—H7A	0.9700
Co1—N1i	2.1515 (17)	C7—H7B	0.9700
Co1—N1	2.1515 (17)	C8—C9	1.378 (4)
O1—C4	1.249 (3)	C8—H8	0.9300
O2—C4	1.264 (3)	C9—C10	1.369 (3)
O3—C5	1.297 (3)	C9—H9	0.9300
O3—H3	0.8200	C10—C9i	1.369 (3)
O4—C5	1.215 (3)	C10—H10	0.9300
O5—H1W	0.8200	C11—C12	1.387 (4)
N1—C3	1.326 (3)	C11—H11	0.9300
N1—C1	1.374 (3)	C12—C13	1.378 (3)
N2—C3	1.348 (3)	C12—H12	0.9300
N2—C2	1.366 (3)	C13—C14	1.390 (3)
N2—H2	0.8600	C13—C13ii	1.486 (4)
N3—C8	1.340 (3)	C14—C15	1.362 (4)
N3—C8i	1.340 (3)	C14—H14	0.9300
N4—C15	1.322 (4)	C15—H15	0.9300
N4—C11	1.327 (4)	C7'—C6'i	1.667 (13)
C1—C2	1.367 (3)	C7'—C6'	1.667 (13)
C1—C4	1.487 (3)	C7'—H7'1	0.9700
C2—C5	1.482 (3)	C7'—H7'2	0.9700
C3—C6	1.478 (6)	C6'—H6'1	0.9700
C3—C6'	1.565 (19)	C6'—H6'2	0.9700
C6—C7	1.557 (6)
O5—Co1—N3	176.35 (10)	C3—C6—H6A	108.6
O5—Co1—O1	87.35 (7)	C7—C6—H6A	108.6
N3—Co1—O1	90.22 (7)	C3—C6—H6B	108.6
O5—Co1—O1i	87.35 (7)	C7—C6—H6B	108.6
N3—Co1—O1i	90.22 (7)	H6A—C6—H6B	107.6
O1—Co1—O1i	96.30 (8)	C6—C7—C6i	110.7 (7)
O5—Co1—N1i	87.43 (7)	C6—C7—H7A	109.5
N3—Co1—N1i	94.74 (7)	C6i—C7—H7A	109.5
O1—Co1—N1i	172.62 (6)	C6—C7—H7B	109.5
O1i—Co1—N1i	78.25 (6)	C6i—C7—H7B	109.5
O5—Co1—N1	87.43 (7)	H7A—C7—H7B	108.1
N3—Co1—N1	94.74 (7)	N3—C8—C9	123.0 (2)
O1—Co1—N1	78.25 (6)	N3—C8—H8	118.5
O1i—Co1—N1	172.62 (6)	C9—C8—H8	118.5
N1i—Co1—N1	106.72 (9)	C10—C9—C8	119.2 (3)
C4—O1—Co1	115.09 (14)	C10—C9—H9	120.4
C5—O3—H3	109.5	C8—C9—H9	120.4
Co1—O5—H1W	109.5	C9—C10—C9i	118.7 (4)
C3—N1—C1	105.87 (18)	C9—C10—H10	120.7
C3—N1—Co1	143.14 (15)	C9i—C10—H10	120.7
C1—N1—Co1	109.78 (13)	N4—C11—C12	124.3 (3)
C3—N2—C2	108.63 (18)	N4—C11—H11	117.8
C3—N2—H2	125.7	C12—C11—H11	117.8
C2—N2—H2	125.7	C13—C12—C11	118.8 (3)
C8—N3—C8i	116.9 (3)	C13—C12—H12	120.6
C8—N3—Co1	121.51 (15)	C11—C12—H12	120.6
C8i—N3—Co1	121.51 (15)	C12—C13—C14	116.7 (2)
C15—N4—C11	116.1 (2)	C12—C13—C13ii	122.5 (3)
C2—C1—N1	110.02 (19)	C14—C13—C13ii	120.9 (3)
C2—C1—C4	131.70 (19)	C15—C14—C13	120.0 (3)
N1—C1—C4	118.24 (18)	C15—C14—H14	120.0
N2—C2—C1	105.15 (18)	C13—C14—H14	120.0
N2—C2—C5	121.5 (2)	N4—C15—C14	124.1 (3)
C1—C2—C5	133.3 (2)	N4—C15—H15	118.0
N1—C3—N2	110.33 (19)	C14—C15—H15	118.0
N1—C3—C6	129.0 (3)	C6'i—C7'—C6'	93.5 (12)
N2—C3—C6	120.4 (3)	C6'i—C7'—H7'1	113.0
N1—C3—C6'	123.2 (7)	C6'—C7'—H7'1	113.0
N2—C3—C6'	125.5 (6)	C6'i—C7'—H7'2	113.0
C6—C3—C6'	14.6 (7)	C6'—C7'—H7'2	113.0
O1—C4—O2	125.2 (2)	H7'1—C7'—H7'2	110.4
O1—C4—C1	117.23 (18)	C3—C6'—C7'	101.5 (9)
O2—C4—C1	117.59 (19)	C3—C6'—H6'1	111.5
O4—C5—O3	122.8 (2)	C7'—C6'—H6'1	111.5
O4—C5—C2	121.0 (2)	C3—C6'—H6'2	111.5
O3—C5—C2	116.2 (2)	C7'—C6'—H6'2	111.5
C3—C6—C7	114.5 (5)	H6'1—C6'—H6'2	109.3
O5—Co1—O1—C4	77.25 (17)	C1—N1—C3—C6	174.5 (5)
N3—Co1—O1—C4	−105.47 (17)	Co1—N1—C3—C6	9.5 (6)
O1i—Co1—O1—C4	164.28 (13)	C1—N1—C3—C6'	−169.0 (6)
N1i—Co1—O1—C4	122.3 (5)	Co1—N1—C3—C6'	26.1 (7)
N1—Co1—O1—C4	−10.68 (16)	C2—N2—C3—N1	−0.1 (3)
O5—Co1—N1—C3	86.0 (3)	C2—N2—C3—C6	−174.9 (4)
N3—Co1—N1—C3	−96.9 (3)	C2—N2—C3—C6'	168.9 (7)
O1—Co1—N1—C3	173.8 (3)	Co1—O1—C4—O2	−169.8 (2)
O1i—Co1—N1—C3	131.0 (5)	Co1—O1—C4—C1	9.7 (3)
N1i—Co1—N1—C3	−0.5 (3)	C2—C1—C4—O1	−178.4 (2)
O5—Co1—N1—C1	−78.58 (15)	N1—C1—C4—O1	−1.1 (3)
N3—Co1—N1—C1	98.49 (15)	C2—C1—C4—O2	1.1 (4)
O1—Co1—N1—C1	9.25 (14)	N1—C1—C4—O2	178.5 (2)
O1i—Co1—N1—C1	−33.6 (6)	N2—C2—C5—O4	−0.9 (4)
N1i—Co1—N1—C1	−165.12 (11)	C1—C2—C5—O4	176.1 (2)
O5—Co1—N3—C8	91.7 (2)	N2—C2—C5—O3	180.0 (2)
O1—Co1—N3—C8	43.6 (2)	C1—C2—C5—O3	−3.1 (4)
O1i—Co1—N3—C8	139.9 (2)	N1—C3—C6—C7	27.9 (8)
N1i—Co1—N3—C8	−141.9 (2)	N2—C3—C6—C7	−158.5 (4)
N1—Co1—N3—C8	−34.6 (2)	C6'—C3—C6—C7	−44 (3)
O5—Co1—N3—C8i	−91.7 (2)	C3—C6—C7—C6i	−114.7 (5)
O1—Co1—N3—C8i	−139.9 (2)	C8i—N3—C8—C9	−1.4 (5)
O1i—Co1—N3—C8i	−43.6 (2)	Co1—N3—C8—C9	175.34 (19)
N1i—Co1—N3—C8i	34.6 (2)	N3—C8—C9—C10	0.1 (4)
N1—Co1—N3—C8i	141.9 (2)	C8—C9—C10—C9i	1.3 (5)
C3—N1—C1—C2	−0.4 (3)	C15—N4—C11—C12	0.6 (4)
Co1—N1—C1—C2	170.09 (15)	N4—C11—C12—C13	−0.2 (4)
C3—N1—C1—C4	−178.2 (2)	C11—C12—C13—C14	−0.2 (4)
Co1—N1—C1—C4	−7.8 (2)	C11—C12—C13—C13ii	179.1 (3)
C3—N2—C2—C1	−0.1 (3)	C12—C13—C14—C15	0.3 (4)
C3—N2—C2—C5	177.6 (2)	C13ii—C13—C14—C15	−179.0 (3)
N1—C1—C2—N2	0.3 (2)	C11—N4—C15—C14	−0.4 (5)
C4—C1—C2—N2	177.8 (2)	C13—C14—C15—N4	0.0 (5)
N1—C1—C2—C5	−177.0 (2)	N1—C3—C6'—C7'	−70.7 (10)
C4—C1—C2—C5	0.5 (4)	N2—C3—C6'—C7'	121.7 (6)
C1—N1—C3—N2	0.3 (3)	C6—C3—C6'—C7'	48 (2)
Co1—N1—C3—N2	−164.64 (19)	C6'i—C7'—C6'—C3	129.0 (6)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2	0.82	1.65	2.473 (2)	177
O5—H1W···N4iii	0.82	1.95	2.727 (3)	157
N2—H2···O4iv	0.86	1.93	2.763 (3)	162

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O2	0.82	1.65	2.473 (2)	177
O5—H1W⋯N4i	0.82	1.95	2.727 (3)	157
N2—H2⋯O4ii	0.86	1.93	2.763 (3)	162

Symmetry codes: (i) ; (ii) .