catena-Poly[bis-[(1,10-phenanthroline)cobalt(II)]-μ(4)-3,6-dicarb-oxy-cyclo-hexane-1,2,4,5-tetra-carboxyl-ato].

In the title compound, [Co(2)(C(12)H(8)O(12))(C(12)H(8)N(2))(2)](n), each 3,6-dicarb-oxy-cyclo-hexane-1,2,4,5-tetra-carboxyl-ate (H(2)chhc(4-)) anion has crystallographically imposed C(2) symmetry and bridges four six-coordinate Co atoms, generating polymeric chains running along [010]. These chains are further extended into a three-dimensional network via O-H⋯O hydrogen-bonding inter-actions and inter-chain π-π stacking inter-actions [centroid-centroid distance = 3.662 (2) Å].

Related literature

For the design and synthesis of coordination polymer complexes and their potential applications, see: Biradha et al. (2006 ▶); Bauer et al. (2007 ▶); Zacher et al. (2011 ▶). For the 1,2,3,4,5,6-cyclo­hexa­nehexa­carboxyl­ate ligand, see: Li et al. (2006 ▶); Wang et al. (2008 ▶); Thuéry & Masci (2010 ▶). For related structures, see: Konar et al. (2004 ▶); Li et al. (2006 ▶).

Experimental

Crystal data

[Co2(C12H8O12)(C12H8N2)2]

M = 822.46

Monoclinic,

a = 22.180 (4) Å

b = 8.9520 (18) Å

c = 16.426 (3) Å

β = 93.33 (3)°

V = 3256.0 (11) Å3

Z = 4

Mo Kα radiation

μ = 1.10 mm−1

T = 295 K

0.31 × 0.23 × 0.15 mm

Data collection

Siemens P4 diffractometer

Absorption correction: ψ scan (XSCANS; Siemens, 1996 ▶) T min = 0.702, T max = 0.784

4566 measured reflections

3753 independent reflections

3312 reflections with I > 2σ(I)

R int = 0.022

3 standard reflections every 97 reflections intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.083

S = 1.03

3753 reflections

248 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.38 e Å−3

Δρmin = −0.33 e Å−3

Data collection: XSCANS (Siemens, 1996 ▶); cell refinement: XSCANS; data reduction: XSCANS; 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: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811019970/sj5153sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811019970/sj5153Isup2.hkl

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

[Co2(C12H8O12)(C12H8N2)2]	F(000) = 1672
Mr = 822.46	Dx = 1.678 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 25 reflections
a = 22.180 (4) Å	θ = 5.0–12.5°
b = 8.9520 (18) Å	µ = 1.10 mm−1
c = 16.426 (3) Å	T = 295 K
β = 93.33 (3)°	Block, pink
V = 3256.0 (11) Å3	0.31 × 0.23 × 0.15 mm
Z = 4

Siemens P4 diffractometer	3312 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.022
graphite	θmax = 27.5°, θmin = 2.5°
θ/2θ scans	h = −28→1
Absorption correction: ψ scan (XSCANS; Siemens, 1996)	k = −1→11
Tmin = 0.702, Tmax = 0.784	l = −21→21
4566 measured reflections	3 standard reflections every 97 reflections
3753 independent reflections	intensity decay: none

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) = 0.083	w = 1/[σ2(Fo2) + (0.0413P)2 + 2.2781P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
3753 reflections	Δρmax = 0.38 e Å−3
248 parameters	Δρmin = −0.33 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: 0.00077 (19)

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.

	x	y	z	Uiso*/Ueq
Co1	0.098444 (9)	0.64743 (2)	0.140367 (13)	0.02138 (9)
O1	0.07208 (6)	0.79951 (15)	0.23735 (7)	0.0330 (3)
O2	0.04781 (7)	0.83776 (14)	0.10892 (7)	0.0327 (3)
O3	0.08305 (7)	1.16900 (18)	0.04746 (9)	0.0433 (4)
O4	−0.01738 (6)	1.14637 (17)	0.04776 (8)	0.0363 (3)
H4A	−0.0159 (12)	1.148 (3)	−0.0004 (19)	0.054*
O5	0.09100 (5)	1.45307 (15)	0.21296 (8)	0.0314 (3)
O6	0.01745 (5)	1.51543 (15)	0.12579 (8)	0.0329 (3)
N1	0.13438 (6)	0.55177 (17)	0.03690 (9)	0.0277 (3)
N2	0.18993 (7)	0.70526 (19)	0.16045 (9)	0.0322 (3)
C1	0.10617 (9)	0.4793 (2)	−0.02411 (11)	0.0378 (4)
H1A	0.0642	0.4771	−0.0272	0.045*
C2	0.13708 (13)	0.4053 (3)	−0.08457 (14)	0.0544 (6)
H2A	0.1159	0.3563	−0.1272	0.065*
C3	0.19861 (13)	0.4065 (3)	−0.07970 (15)	0.0591 (7)
H3A	0.2196	0.3561	−0.1186	0.071*
C4	0.23052 (10)	0.4833 (3)	−0.01624 (14)	0.0472 (5)
C5	0.29531 (12)	0.4955 (4)	−0.00706 (19)	0.0673 (8)
H5A	0.3186	0.4468	−0.0441	0.081*
C6	0.32300 (10)	0.5748 (4)	0.05321 (19)	0.0686 (9)
H6A	0.3649	0.5806	0.0569	0.082*
C7	0.28897 (9)	0.6512 (3)	0.11216 (16)	0.0517 (6)
C8	0.31442 (11)	0.7393 (4)	0.17623 (18)	0.0660 (8)
H8A	0.3561	0.7516	0.1821	0.079*
C9	0.27855 (12)	0.8067 (4)	0.22961 (17)	0.0658 (8)
H9A	0.2954	0.8650	0.2719	0.079*
C10	0.21599 (11)	0.7875 (3)	0.22011 (14)	0.0487 (5)
H10A	0.1917	0.8338	0.2568	0.058*
C11	0.22540 (8)	0.6391 (2)	0.10648 (12)	0.0339 (4)
C12	0.19595 (8)	0.5557 (2)	0.04106 (11)	0.0318 (4)
C13	0.00497 (7)	1.00717 (17)	0.20407 (9)	0.0213 (3)
H13A	−0.0344	0.9985	0.1741	0.026*
C14	0.03623 (7)	1.15052 (16)	0.17600 (9)	0.0205 (3)
H14A	0.0778	1.1519	0.1998	0.025*
C15	0.00349 (7)	1.29201 (17)	0.20377 (9)	0.0194 (3)
H15A	−0.0367	1.2958	0.1758	0.023*
C16	0.04335 (8)	0.87293 (17)	0.18323 (10)	0.0234 (3)
C17	0.03790 (8)	1.15477 (18)	0.08330 (10)	0.0256 (3)
C18	0.03920 (7)	1.42928 (17)	0.17948 (9)	0.0209 (3)

	U11	U22	U33	U12	U13	U23
Co1	0.02179 (13)	0.01718 (13)	0.02545 (13)	−0.00066 (8)	0.00385 (8)	−0.00008 (8)
O1	0.0451 (7)	0.0284 (6)	0.0258 (6)	0.0125 (6)	0.0031 (5)	0.0002 (5)
O2	0.0497 (8)	0.0259 (6)	0.0228 (6)	0.0115 (6)	0.0048 (5)	−0.0013 (5)
O3	0.0426 (8)	0.0505 (9)	0.0389 (7)	0.0011 (7)	0.0212 (6)	0.0015 (6)
O4	0.0402 (7)	0.0477 (9)	0.0209 (6)	0.0031 (6)	0.0014 (5)	−0.0005 (6)
O5	0.0286 (6)	0.0283 (6)	0.0368 (6)	−0.0066 (5)	−0.0040 (5)	0.0084 (5)
O6	0.0274 (6)	0.0276 (6)	0.0431 (7)	−0.0037 (5)	−0.0031 (5)	0.0141 (6)
N1	0.0265 (7)	0.0298 (7)	0.0272 (7)	0.0006 (6)	0.0044 (5)	−0.0008 (6)
N2	0.0299 (7)	0.0335 (8)	0.0328 (7)	−0.0094 (6)	−0.0004 (6)	0.0029 (7)
C1	0.0407 (10)	0.0412 (11)	0.0313 (9)	−0.0015 (8)	0.0005 (7)	−0.0037 (8)
C2	0.0764 (17)	0.0522 (14)	0.0353 (11)	−0.0025 (13)	0.0089 (10)	−0.0145 (10)
C3	0.0742 (17)	0.0589 (15)	0.0469 (13)	0.0132 (14)	0.0256 (12)	−0.0108 (12)
C4	0.0444 (11)	0.0513 (13)	0.0479 (12)	0.0140 (10)	0.0206 (9)	0.0045 (10)
C5	0.0411 (13)	0.086 (2)	0.0782 (18)	0.0230 (14)	0.0307 (13)	0.0099 (17)
C6	0.0245 (10)	0.096 (2)	0.087 (2)	0.0121 (13)	0.0166 (11)	0.0225 (18)
C7	0.0236 (9)	0.0692 (17)	0.0620 (14)	−0.0055 (9)	0.0005 (9)	0.0216 (12)
C8	0.0310 (11)	0.092 (2)	0.0729 (17)	−0.0238 (13)	−0.0132 (11)	0.0211 (16)
C9	0.0571 (15)	0.081 (2)	0.0564 (15)	−0.0368 (15)	−0.0180 (12)	0.0040 (14)
C10	0.0505 (13)	0.0511 (13)	0.0438 (11)	−0.0208 (11)	−0.0043 (9)	−0.0023 (10)
C11	0.0229 (8)	0.0386 (10)	0.0404 (10)	−0.0019 (7)	0.0025 (7)	0.0106 (8)
C12	0.0278 (8)	0.0337 (9)	0.0348 (9)	0.0038 (7)	0.0091 (7)	0.0062 (8)
C13	0.0275 (7)	0.0155 (7)	0.0213 (7)	−0.0008 (6)	0.0037 (6)	−0.0001 (6)
C14	0.0228 (7)	0.0161 (7)	0.0227 (7)	−0.0001 (6)	0.0036 (5)	0.0001 (6)
C15	0.0209 (7)	0.0157 (7)	0.0217 (7)	0.0000 (5)	0.0020 (5)	0.0003 (6)
C16	0.0302 (8)	0.0168 (7)	0.0238 (7)	−0.0003 (6)	0.0051 (6)	0.0008 (6)
C17	0.0342 (8)	0.0179 (7)	0.0252 (8)	0.0015 (6)	0.0077 (6)	0.0009 (6)
C18	0.0238 (7)	0.0167 (7)	0.0228 (7)	0.0008 (6)	0.0058 (6)	−0.0014 (6)

Co1—O1	2.2002 (13)	C3—H3A	0.9300
Co1—O2	2.0890 (13)	C4—C12	1.406 (3)
Co1—O5i	2.1211 (13)	C4—C5	1.440 (3)
Co1—O6i	2.1519 (13)	C5—C6	1.338 (5)
Co1—N1	2.1012 (15)	C5—H5A	0.9300
Co1—N2	2.1016 (15)	C6—C7	1.435 (4)
Co1—C18i	2.4599 (16)	C6—H6A	0.9300
Co1—C16	2.4827 (16)	C7—C8	1.407 (4)
O1—C16	1.250 (2)	C7—C11	1.412 (3)
O2—C16	1.270 (2)	C8—C9	1.359 (4)
O3—C17	1.198 (2)	C8—H8A	0.9300
O4—C17	1.329 (2)	C9—C10	1.398 (3)
O4—H4A	0.79 (3)	C9—H9A	0.9300
O5—C18	1.263 (2)	C10—H10A	0.9300
O5—Co1ii	2.1211 (13)	C11—C12	1.435 (3)
O6—C18	1.247 (2)	C13—C16	1.523 (2)
O6—Co1ii	2.1519 (13)	C13—C13iii	1.538 (3)
N1—C1	1.321 (2)	C13—C14	1.542 (2)
N1—C12	1.364 (2)	C13—H13A	0.9800
N2—C10	1.330 (3)	C14—C17	1.526 (2)
N2—C11	1.355 (3)	C14—C15	1.542 (2)
C1—C2	1.405 (3)	C14—H14A	0.9800
C1—H1A	0.9300	C15—C18	1.528 (2)
C2—C3	1.363 (4)	C15—C15iii	1.535 (3)
C2—H2A	0.9300	C15—H15A	0.9800
C3—C4	1.405 (4)	C18—Co1ii	2.4599 (16)
O2—Co1—N1	110.87 (6)	C5—C6—C7	121.0 (2)
O2—Co1—N2	109.77 (6)	C5—C6—H6A	119.5
N1—Co1—N2	79.58 (6)	C7—C6—H6A	119.5
O2—Co1—O5i	138.57 (6)	C8—C7—C11	116.6 (2)
N1—Co1—O5i	99.55 (6)	C8—C7—C6	124.6 (2)
N2—Co1—O5i	102.70 (6)	C11—C7—C6	118.8 (2)
O2—Co1—O6i	89.26 (5)	C9—C8—C7	120.5 (2)
N1—Co1—O6i	92.27 (6)	C9—C8—H8A	119.8
N2—Co1—O6i	160.89 (6)	C7—C8—H8A	119.8
O5i—Co1—O6i	61.34 (5)	C8—C9—C10	119.2 (2)
O2—Co1—O1	60.84 (5)	C8—C9—H9A	120.4
N1—Co1—O1	165.26 (6)	C10—C9—H9A	120.4
N2—Co1—O1	91.64 (6)	N2—C10—C9	122.4 (2)
O5i—Co1—O1	93.89 (5)	N2—C10—H10A	118.8
O6i—Co1—O1	99.50 (6)	C9—C10—H10A	118.8
O2—Co1—C18i	115.12 (6)	N2—C11—C7	122.6 (2)
N1—Co1—C18i	96.96 (6)	N2—C11—C12	117.47 (15)
N2—Co1—C18i	132.85 (6)	C7—C11—C12	119.9 (2)
O5i—Co1—C18i	30.88 (5)	N1—C12—C4	122.56 (19)
O6i—Co1—C18i	30.46 (5)	N1—C12—C11	117.50 (16)
O1—Co1—C18i	97.68 (5)	C4—C12—C11	119.94 (18)
O2—Co1—C16	30.74 (5)	C16—C13—C13iii	109.53 (11)
N1—Co1—C16	140.98 (6)	C16—C13—C14	108.82 (12)
N2—Co1—C16	104.00 (6)	C13iii—C13—C14	112.70 (10)
O5i—Co1—C16	116.86 (6)	C16—C13—H13A	108.6
O6i—Co1—C16	93.24 (6)	C13iii—C13—H13A	108.6
O1—Co1—C16	30.20 (5)	C14—C13—H13A	108.6
C18i—Co1—C16	106.99 (5)	C17—C14—C13	110.89 (13)
C16—O1—Co1	87.50 (10)	C17—C14—C15	108.29 (12)
C16—O2—Co1	92.02 (10)	C13—C14—C15	111.56 (12)
C17—O4—H4A	110 (2)	C17—C14—H14A	108.7
C18—O5—Co1ii	89.55 (10)	C13—C14—H14A	108.7
C18—O6—Co1ii	88.55 (10)	C15—C14—H14A	108.7
C1—N1—C12	118.65 (16)	C18—C15—C15iii	109.99 (10)
C1—N1—Co1	128.96 (13)	C18—C15—C14	108.86 (12)
C12—N1—Co1	112.02 (12)	C15iii—C15—C14	111.64 (10)
C10—N2—C11	118.66 (18)	C18—C15—H15A	108.8
C10—N2—Co1	128.76 (15)	C15iii—C15—H15A	108.8
C11—N2—Co1	112.44 (12)	C14—C15—H15A	108.8
N1—C1—C2	122.6 (2)	O1—C16—O2	119.22 (15)
N1—C1—H1A	118.7	O1—C16—C13	121.57 (14)
C2—C1—H1A	118.7	O2—C16—C13	119.17 (14)
C3—C2—C1	118.9 (2)	O1—C16—Co1	62.30 (9)
C3—C2—H2A	120.6	O2—C16—Co1	57.23 (8)
C1—C2—H2A	120.6	C13—C16—Co1	174.86 (12)
C2—C3—C4	120.5 (2)	O3—C17—O4	124.52 (17)
C2—C3—H3A	119.8	O3—C17—C14	124.24 (17)
C4—C3—H3A	119.8	O4—C17—C14	111.20 (14)
C3—C4—C12	116.8 (2)	O6—C18—O5	120.56 (15)
C3—C4—C5	124.8 (2)	O6—C18—C15	119.79 (14)
C12—C4—C5	118.3 (2)	O5—C18—C15	119.64 (14)
C6—C5—C4	122.0 (2)	O6—C18—Co1ii	60.99 (9)
C6—C5—H5A	119.0	O5—C18—Co1ii	59.57 (8)
C4—C5—H5A	119.0	C15—C18—Co1ii	178.92 (11)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4A···O2iv	0.79 (3)	1.89 (3)	2.627 (2)	156 (2)

Table 1

Selected bond lengths (Å)

Co1—O1	2.2002 (13)
Co1—O2	2.0890 (13)
Co1—O5i	2.1211 (13)
Co1—O6i	2.1519 (13)
Co1—N1	2.1012 (15)
Co1—N2	2.1016 (15)

Symmetry code: (i) .

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4A⋯O2ii	0.79 (3)	1.89 (3)	2.627 (2)	156 (2)

Symmetry code: (ii) .