catena-Poly[[bis-(4-carboxy-cyclo-hexane-carboxyl-ato-κO,O)cadmium(II)]-μ-1,4-bis-(imidazol-1-ylmeth-yl)benzene-κN:N].

In the title coordination polymer, [Cd(C(8)H(11)O(4))(2)(C(14)H(14)N(4))](n), the Cd atom (site symmetry 2) is six-coordin-ated by two O,O'-bidentate 4-carboxy-cyclo-hexa-necarboxyl-ate (Hchdc) ligands and two N atoms from two different 1,4-bis-(imidazol-1-ylmeth-yl)benzene (1,4-bix) mol-ecules in a very distorted cis-CdN(2)O(4) octa-hedral environment. The 1,4-bix mol-ecules act as bridging ligands that bind two Cd(II) atoms, thus forming an infinite chain propagating in [100], which is decorated by the Hchdc anions. The structure is completed by O-H⋯O hydrogen bonds, which link the chains together.

Related literature

For related structures, see: Qi et al. (2003 ▶). For background to coordination polymers, see: Chen & Liu (2002 ▶); Fang et al. (2006 ▶); Kim & Jung (2002 ▶); Lehn (1990 ▶); Batten & Robson (1998 ▶); Yang et al. (2008 ▶).

Experimental

Crystal data

[Cd(C8H11O4)2(C14H14N4)]

M = 693.03

Orthorhombic,

a = 12.6317 (5) Å

b = 19.9697 (12) Å

c = 12.3703 (7) Å

V = 3120.4 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.75 mm−1

T = 292 K

0.26 × 0.22 × 0.17 mm

Data collection

Oxford Diffraction Gemini R Ultra diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006 ▶) T min = 0.816, T max = 0.882

26676 measured reflections

3190 independent reflections

1658 reflections with I > 2σ(I)

R int = 0.116

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.120

S = 0.95

3190 reflections

195 parameters

H-atom parameters constrained

Δρmax = 0.62 e Å−3

Δρmin = −0.30 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 ▶); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2006 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL-Plus (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809021618/hb2986sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809021618/hb2986Isup2.hkl

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

[Cd(C8H11O4)2(C14H14N4)]	F(000) = 1424
Mr = 693.03	Dx = 1.475 Mg m−3
Orthorhombic, Pccn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ab 2ac	Cell parameters from 3190 reflections
a = 12.6317 (5) Å	θ = 3.0–26.5°
b = 19.9697 (12) Å	µ = 0.75 mm−1
c = 12.3703 (7) Å	T = 292 K
V = 3120.4 (3) Å3	Block, colorless
Z = 4	0.26 × 0.22 × 0.17 mm

Oxford Diffraction Gemini R Ultra diffractometer	3190 independent reflections
Radiation source: fine-focus sealed tube	1658 reflections with I > 2σ(I)
graphite	Rint = 0.116
Detector resolution: 10.0 pixels mm-1	θmax = 26.5°, θmin = 4.7°
ω scans	h = −15→15
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006)	k = −24→24
Tmin = 0.816, Tmax = 0.882	l = −15→15
26676 measured reflections

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120	H-atom parameters constrained
S = 0.95	w = 1/[σ2(Fo2) + (0.0575P)2] where P = (Fo2 + 2Fc2)/3
3190 reflections	(Δ/σ)max < 0.001
195 parameters	Δρmax = 0.62 e Å−3
0 restraints	Δρmin = −0.30 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
C1	0.7200 (5)	0.1255 (3)	0.1946 (5)	0.0556 (16)
C2	0.7134 (5)	0.0551 (3)	0.1562 (5)	0.0703 (18)
H2	0.6472	0.0495	0.1158	0.084*
C3	0.8075 (6)	0.0347 (3)	0.0813 (6)	0.089 (2)
H3A	0.8072	0.0627	0.0172	0.107*
H3B	0.8738	0.0420	0.1190	0.107*
C4	0.7998 (7)	−0.0363 (4)	0.0488 (6)	0.106 (3)
H4A	0.8606	−0.0478	0.0045	0.127*
H4B	0.7367	−0.0427	0.0054	0.127*
C5	0.7956 (5)	−0.0833 (3)	0.1467 (6)	0.082 (2)
H5	0.7788	−0.1281	0.1192	0.099*
C6	0.7065 (7)	−0.0639 (4)	0.2243 (7)	0.098 (2)
H6A	0.6387	−0.0729	0.1905	0.118*
H6B	0.7113	−0.0910	0.2891	0.118*
C7	0.7123 (6)	0.0065 (3)	0.2537 (6)	0.089 (2)
H7A	0.7758	0.0137	0.2961	0.107*
H7B	0.6521	0.0172	0.2992	0.107*
C8	0.9032 (6)	−0.0881 (3)	0.2022 (7)	0.078 (2)
C9	0.9060 (3)	0.2554 (3)	0.4765 (4)	0.0524 (13)
H9	0.8851	0.2997	0.4856	0.063*
C10	0.9221 (4)	0.1567 (3)	0.4138 (5)	0.0657 (16)
H10	0.9152	0.1192	0.3699	0.079*
C11	0.9818 (5)	0.1601 (3)	0.5038 (5)	0.0665 (18)
H11	1.0218	0.1258	0.5339	0.080*
C12	1.0206 (3)	0.2510 (3)	0.6389 (4)	0.0612 (14)
H12A	0.9962	0.2257	0.7010	0.073*
H12B	0.9972	0.2969	0.6481	0.073*
C13	1.1951 (4)	0.2506 (5)	0.5441 (5)	0.125 (4)
H13	1.1592	0.2521	0.4785	0.150*
C14	1.1390 (3)	0.2497 (3)	0.6368 (4)	0.0479 (11)
C15	1.1954 (4)	0.2499 (4)	0.7277 (5)	0.0693 (15)
H15	1.1599	0.2498	0.7936	0.083*
N1	0.8735 (3)	0.2166 (2)	0.3967 (4)	0.0527 (11)
N2	0.9721 (3)	0.2237 (2)	0.5420 (4)	0.0515 (12)
O1	0.7903 (3)	0.1640 (2)	0.1601 (3)	0.0683 (11)
O2	0.6563 (3)	0.1466 (2)	0.2657 (4)	0.0700 (12)
O3	0.9194 (5)	−0.0730 (3)	0.2950 (5)	0.120 (2)
O4	0.9764 (4)	−0.1119 (2)	0.1406 (4)	0.0951 (15)
H4	1.0323	−0.1134	0.1741	0.143*
Cd1	0.7500	0.2500	0.27740 (4)	0.04487 (19)

	U11	U22	U33	U12	U13	U23
C1	0.062 (4)	0.045 (3)	0.059 (4)	0.007 (3)	−0.007 (3)	0.005 (3)
C2	0.096 (5)	0.045 (3)	0.069 (4)	0.000 (3)	0.000 (4)	0.002 (3)
C3	0.149 (6)	0.058 (4)	0.061 (4)	−0.006 (4)	0.036 (5)	0.000 (4)
C4	0.118 (6)	0.103 (6)	0.096 (6)	0.048 (5)	−0.013 (5)	−0.008 (5)
C5	0.085 (4)	0.068 (4)	0.093 (6)	0.022 (4)	−0.020 (4)	0.014 (4)
C6	0.095 (5)	0.078 (5)	0.123 (7)	0.020 (4)	0.014 (5)	0.016 (5)
C7	0.111 (6)	0.065 (4)	0.092 (6)	−0.013 (4)	0.027 (4)	0.005 (4)
C8	0.089 (5)	0.058 (4)	0.087 (6)	0.029 (4)	−0.001 (4)	0.002 (4)
C9	0.036 (2)	0.060 (3)	0.062 (3)	0.015 (3)	−0.002 (3)	0.001 (4)
C10	0.067 (4)	0.055 (4)	0.075 (5)	0.009 (3)	−0.018 (3)	0.002 (3)
C11	0.060 (4)	0.062 (4)	0.077 (5)	0.014 (3)	−0.018 (3)	0.006 (3)
C12	0.037 (2)	0.094 (4)	0.052 (3)	0.009 (4)	−0.006 (2)	0.000 (4)
C13	0.042 (3)	0.291 (12)	0.042 (4)	−0.020 (7)	−0.008 (3)	−0.003 (6)
C14	0.040 (2)	0.062 (3)	0.042 (3)	−0.002 (3)	0.001 (2)	−0.009 (4)
C15	0.048 (3)	0.119 (5)	0.041 (3)	−0.006 (5)	0.004 (2)	−0.004 (5)
N1	0.039 (2)	0.056 (3)	0.064 (3)	0.000 (2)	−0.007 (2)	0.006 (3)
N2	0.030 (2)	0.069 (3)	0.056 (3)	−0.0009 (19)	−0.002 (2)	0.006 (2)
O1	0.083 (3)	0.058 (2)	0.064 (3)	0.001 (2)	0.021 (2)	−0.004 (2)
O2	0.051 (2)	0.059 (2)	0.100 (3)	−0.0010 (18)	0.015 (2)	−0.025 (2)
O3	0.143 (5)	0.130 (5)	0.088 (4)	0.059 (4)	−0.019 (4)	−0.005 (4)
O4	0.077 (3)	0.099 (4)	0.110 (4)	0.027 (3)	−0.007 (3)	−0.027 (3)
Cd1	0.0318 (2)	0.0523 (3)	0.0505 (3)	0.0036 (3)	0.000	0.000

C1—O1	1.250 (6)	C9—N2	1.325 (7)
C1—O2	1.265 (6)	C9—H9	0.9300
C1—C2	1.487 (8)	C10—C11	1.347 (8)
C1—Cd1	2.716 (6)	C10—N1	1.361 (6)
C2—C7	1.548 (8)	C10—H10	0.9300
C2—C3	1.561 (8)	C11—N2	1.360 (7)
C2—H2	0.9800	C11—H11	0.9300
C3—C4	1.478 (9)	C12—N2	1.453 (7)
C3—H3A	0.9700	C12—C14	1.496 (6)
C3—H3B	0.9700	C12—H12A	0.9700
C4—C5	1.533 (10)	C12—H12B	0.9700
C4—H4A	0.9700	C13—C14	1.347 (7)
C4—H4B	0.9700	C13—C13i	1.388 (11)
C5—C8	1.526 (9)	C13—H13	0.9300
C5—C6	1.529 (9)	C14—C15	1.331 (7)
C5—H5	0.9800	C15—C15i	1.379 (10)
C6—C7	1.453 (9)	C15—H15	0.9300
C6—H6A	0.9700	O4—H4	0.8200
C6—H6B	0.9700	Cd1—N1	2.249 (4)
C7—H7A	0.9700	Cd1—O1	2.306 (4)
C7—H7B	0.9700	Cd1—O2	2.384 (4)
C8—O3	1.205 (8)	Cd1—N1ii	2.249 (4)
C8—O4	1.288 (8)	Cd1—O1ii	2.306 (4)
C9—N1	1.320 (7)	Cd1—O2ii	2.384 (4)
O1—C1—O2	119.0 (5)	C11—C10—N1	109.7 (5)
O1—C1—C2	120.8 (5)	C11—C10—H10	125.2
O2—C1—C2	120.2 (6)	N1—C10—H10	125.2
C1—C2—C7	110.2 (5)	C10—C11—N2	106.5 (5)
C1—C2—C3	113.2 (5)	C10—C11—H11	126.8
C7—C2—C3	107.8 (5)	N2—C11—H11	126.8
C1—C2—H2	108.5	N2—C12—C14	113.6 (4)
C7—C2—H2	108.5	N2—C12—H12A	108.8
C3—C2—H2	108.5	C14—C12—H12A	108.8
C4—C3—C2	111.2 (6)	N2—C12—H12B	108.8
C4—C3—H3A	109.4	C14—C12—H12B	108.8
C2—C3—H3A	109.4	H12A—C12—H12B	107.7
C4—C3—H3B	109.4	C14—C13—C13i	121.7 (3)
C2—C3—H3B	109.4	C14—C13—H13	119.2
H3A—C3—H3B	108.0	C13i—C13—H13	119.2
C3—C4—C5	112.0 (6)	C15—C14—C13	115.9 (4)
C3—C4—H4A	109.2	C15—C14—C12	121.3 (4)
C5—C4—H4A	109.2	C13—C14—C12	122.7 (5)
C3—C4—H4B	109.2	C14—C15—C15i	122.4 (3)
C5—C4—H4B	109.2	C14—C15—H15	118.8
H4A—C4—H4B	107.9	C15i—C15—H15	118.8
C8—C5—C6	112.9 (6)	C9—N1—C10	105.1 (5)
C8—C5—C4	111.2 (6)	C9—N1—Cd1	122.2 (4)
C6—C5—C4	111.5 (6)	C10—N1—Cd1	132.5 (4)
C8—C5—H5	106.9	C9—N2—C11	106.9 (5)
C6—C5—H5	106.9	C9—N2—C12	126.2 (5)
C4—C5—H5	106.9	C11—N2—C12	126.8 (5)
C7—C6—C5	111.5 (6)	C1—O1—Cd1	94.9 (3)
C7—C6—H6A	109.3	C1—O2—Cd1	90.9 (3)
C5—C6—H6A	109.3	C8—O4—H4	109.5
C7—C6—H6B	109.3	N1—Cd1—N1ii	97.9 (2)
C5—C6—H6B	109.3	N1—Cd1—O1	92.24 (16)
H6A—C6—H6B	108.0	N1ii—Cd1—O1	141.92 (15)
C6—C7—C2	114.3 (6)	N1—Cd1—O1ii	141.92 (15)
C6—C7—H7A	108.7	N1ii—Cd1—O1ii	92.24 (16)
C2—C7—H7A	108.7	O1—Cd1—O1ii	102.0 (2)
C6—C7—H7B	108.7	N1—Cd1—O2	97.33 (15)
C2—C7—H7B	108.7	N1ii—Cd1—O2	87.24 (15)
H7A—C7—H7B	107.6	O1—Cd1—O2	55.00 (14)
O3—C8—O4	122.2 (7)	O1ii—Cd1—O2	119.83 (15)
O3—C8—C5	124.4 (7)	N1—Cd1—O2ii	87.24 (15)
O4—C8—C5	113.3 (7)	N1ii—Cd1—O2ii	97.33 (15)
N1—C9—N2	111.8 (6)	O1—Cd1—O2ii	119.83 (15)
N1—C9—H9	124.1	O1ii—Cd1—O2ii	55.00 (14)
N2—C9—H9	124.1	O2—Cd1—O2ii	173.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O2iii	0.82	1.86	2.644 (6)	161

Cd1—N1	2.249 (4)
Cd1—O1	2.306 (4)
Cd1—O2	2.384 (4)

O1—Cd1—O2

55.00 (14)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4⋯O2i	0.82	1.86	2.644 (6)	161

Symmetry code: (i) .