Poly[bis-(1H-imidazole)(μ(3)-7-oxabicyclo-[2.2.1]heptane-2,3-dicarboxyl-ato)cadmium(II)].

The title compound, [Cd(C(8)H(8)O(5))(C(3)H(4)N(2))(2)](n), was synthesized by the reaction of 7-oxabicyclo-[2.2.1]heptane-2,3-dicarboxylic anhydride, cadmium acetate and imidazole. The Cd(II) atom is seven-coordinated in a distorted penta-gonal-bipyramidal configuration by five O atoms from carboxyl-ate groups of three 7-oxabicyclo-[2.2.1]heptane-2,3-dicarboxylate ligands and two N atoms from two imidazole ligands. The crystal structure is stabilized by N-H⋯O and C-H⋯O hydrogen-bonding and C-H⋯π inter-actions.

Related literature

7-Oxabicyclo­[2.2.1]heptane-2,3-dicarboxylic anhydride (nor­cantharidin) is a lower toxicity anti­cancer drug, see: Shimi et al. (1982 ▶). For cobalt complexes of norcantharidin, see: Wang et al. (1988 ▶) and of imidazole, see: Furenlid et al. (1986 ▶); Zhu et al. (2003 ▶).

Experimental

Crystal data

[Cd(C8H8O5)(C3H4N2)2]

M = 432.71

Monoclinic,

a = 12.5374 (16) Å

b = 9.6596 (13) Å

c = 14.1635 (17) Å

β = 112.761 (7)°

V = 1581.7 (3) Å3

Z = 4

Mo Kα radiation

μ = 1.41 mm−1

T = 296 K

0.12 × 0.06 × 0.05 mm

Data collection

Bruker APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.900, T max = 0.932

10791 measured reflections

2777 independent reflections

2310 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.075

wR(F 2) = 0.216

S = 1.05

2777 reflections

217 parameters

234 restraints

H-atom parameters constrained

Δρmax = 2.92 e Å−3

Δρmin = −1.26 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); 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: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809021801/at2804sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809021801/at2804Isup2.hkl

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

[Cd(C8H8O5)(C3H4N2)2]	F(000) = 864
Mr = 432.71	Dx = 1.817 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3164 reflections
a = 12.5374 (16) Å	θ = 1.8–25.0°
b = 9.6596 (13) Å	µ = 1.41 mm−1
c = 14.1635 (17) Å	T = 296 K
β = 112.761 (7)°	Block, colourless
V = 1581.7 (3) Å3	0.12 × 0.06 × 0.05 mm
Z = 4

Bruker APEXII area-detector diffractometer	2777 independent reflections
Radiation source: fine-focus sealed tube	2310 reflections with I > 2σ(I)
graphite	Rint = 0.035
ω scans	θmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→13
Tmin = 0.900, Tmax = 0.932	k = −9→11
10791 measured reflections	l = −16→16

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)] = 0.075	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.216	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.1141P)2 + 20.9278P] where P = (Fo2 + 2Fc2)/3
2777 reflections	(Δ/σ)max < 0.001
217 parameters	Δρmax = 2.92 e Å−3
234 restraints	Δρmin = −1.26 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
Cd1	0.56124 (6)	0.12069 (7)	0.41461 (5)	0.0343 (3)
C1	0.3497 (10)	−0.0468 (14)	0.3258 (10)	0.054 (2)
C2	0.2845 (10)	−0.2300 (14)	0.1484 (11)	0.057 (2)
C3	0.2272 (12)	−0.0995 (16)	0.2847 (13)	0.072 (2)
H3A	0.2224	−0.1610	0.3380	0.086*
C4	0.1928 (11)	−0.1894 (18)	0.1877 (12)	0.073 (2)
H4A	0.1672	−0.2772	0.2066	0.088*
C5	0.1415 (13)	−0.0051 (18)	0.2677 (13)	0.083 (3)
H5A	0.1617	0.0762	0.3126	0.099*
C6	0.0917 (13)	−0.1236 (17)	0.1263 (14)	0.080 (3)
H6A	0.0743	−0.1363	0.0532	0.096*
C7	0.0267 (13)	−0.0946 (18)	0.2649 (14)	0.083 (3)
H7A	0.0478	−0.1647	0.3180	0.100*
H7B	−0.0321	−0.0346	0.2715	0.100*
C8	−0.0141 (13)	−0.1606 (19)	0.1553 (13)	0.081 (3)
H8A	−0.0851	−0.1187	0.1084	0.097*
H8B	−0.0246	−0.2599	0.1573	0.097*
C9	0.7916 (10)	−0.0684 (14)	0.4431 (9)	0.054 (3)
H9A	0.8443	−0.0022	0.4815	0.064*
C10	0.8193 (11)	−0.1875 (15)	0.4113 (10)	0.060 (3)
H10A	0.8935	−0.2187	0.4231	0.072*
C11	0.6339 (10)	−0.1723 (13)	0.3608 (9)	0.051 (2)
H11A	0.5560	−0.1953	0.3299	0.061*
C12	0.3507 (10)	0.3209 (13)	0.4170 (9)	0.050 (2)
H12A	0.3139	0.2518	0.4388	0.060*
C13	0.3119 (11)	0.4481 (13)	0.3898 (10)	0.055 (3)
H13A	0.2432	0.4845	0.3897	0.066*
C14	0.4742 (10)	0.4295 (13)	0.3745 (9)	0.050 (2)
H14A	0.5396	0.4509	0.3616	0.060*
N1	0.4556 (8)	0.3092 (9)	0.4073 (6)	0.0389 (19)
N2	0.3900 (9)	0.5160 (10)	0.3620 (8)	0.055 (3)
H2A	0.3849	0.5999	0.3404	0.066*
N3	0.6737 (7)	−0.0577 (9)	0.4109 (6)	0.0385 (19)
N4	0.7219 (10)	−0.2529 (10)	0.3601 (8)	0.058 (3)
H4B	0.7153	−0.3326	0.3313	0.070*
O1	0.1232 (10)	0.0205 (13)	0.1600 (10)	0.102 (3)
O2	0.3853 (6)	0.0273 (8)	0.2739 (6)	0.0493 (16)
O3	0.4150 (8)	−0.0683 (11)	0.4176 (6)	0.064 (2)
O4	0.2664 (7)	−0.2321 (9)	0.0572 (7)	0.0558 (18)
O5	0.3769 (6)	−0.2772 (8)	0.2164 (5)	0.0425 (15)

	U11	U22	U33	U12	U13	U23
Cd1	0.0361 (5)	0.0323 (5)	0.0371 (5)	0.0007 (3)	0.0170 (3)	0.0026 (3)
C1	0.042 (4)	0.063 (4)	0.067 (4)	−0.001 (3)	0.032 (3)	−0.023 (4)
C2	0.039 (4)	0.064 (5)	0.076 (5)	−0.007 (4)	0.032 (4)	−0.028 (4)
C3	0.049 (4)	0.082 (5)	0.089 (5)	−0.006 (4)	0.031 (4)	−0.034 (4)
C4	0.048 (4)	0.083 (5)	0.091 (5)	−0.003 (4)	0.029 (4)	−0.035 (4)
C5	0.059 (4)	0.087 (5)	0.095 (5)	−0.004 (4)	0.023 (4)	−0.029 (4)
C6	0.054 (4)	0.085 (5)	0.094 (5)	−0.004 (4)	0.021 (4)	−0.030 (4)
C7	0.055 (5)	0.097 (5)	0.097 (5)	−0.004 (4)	0.029 (4)	−0.030 (5)
C8	0.055 (4)	0.091 (5)	0.096 (5)	−0.003 (4)	0.028 (4)	−0.032 (5)
C9	0.041 (5)	0.056 (6)	0.060 (5)	0.011 (5)	0.014 (4)	0.002 (5)
C10	0.047 (5)	0.064 (6)	0.067 (6)	0.016 (5)	0.018 (5)	0.001 (5)
C11	0.043 (4)	0.052 (5)	0.057 (5)	0.006 (4)	0.020 (4)	−0.001 (4)
C12	0.044 (5)	0.053 (5)	0.064 (5)	0.003 (4)	0.033 (4)	0.000 (4)
C13	0.051 (5)	0.052 (5)	0.068 (6)	0.007 (5)	0.029 (5)	0.003 (5)
C14	0.050 (5)	0.050 (5)	0.057 (5)	−0.002 (5)	0.029 (4)	0.001 (5)
N1	0.049 (5)	0.030 (4)	0.041 (4)	−0.001 (4)	0.021 (4)	−0.003 (4)
N2	0.071 (7)	0.032 (5)	0.065 (6)	0.014 (5)	0.031 (5)	0.013 (4)
N3	0.037 (5)	0.037 (5)	0.041 (5)	0.003 (4)	0.015 (4)	0.001 (4)
N4	0.087 (8)	0.038 (5)	0.054 (6)	0.017 (5)	0.031 (5)	−0.007 (4)
O1	0.081 (5)	0.090 (6)	0.109 (6)	0.012 (5)	0.006 (5)	0.000 (5)
O2	0.046 (3)	0.050 (4)	0.060 (4)	0.001 (3)	0.029 (3)	0.006 (3)
O3	0.066 (5)	0.086 (5)	0.046 (4)	0.018 (4)	0.028 (3)	0.004 (4)
O4	0.050 (4)	0.055 (4)	0.060 (4)	0.011 (3)	0.019 (3)	−0.002 (3)
O5	0.045 (3)	0.042 (4)	0.046 (3)	0.003 (3)	0.024 (3)	−0.005 (3)

Cd1—N1	2.230 (9)	C7—H7A	0.9700
Cd1—N3	2.240 (9)	C7—H7B	0.9700
Cd1—O3i	2.333 (8)	C8—H8A	0.9700
Cd1—O5ii	2.476 (7)	C8—H8B	0.9700
Cd1—O4ii	2.487 (8)	C9—C10	1.329 (18)
Cd1—O2	2.500 (8)	C9—N3	1.372 (14)
Cd1—O3	2.599 (10)	C9—H9A	0.9300
C1—O2	1.226 (15)	C10—N4	1.316 (17)
C1—O3	1.258 (15)	C10—H10A	0.9300
C1—C3	1.506 (17)	C11—N3	1.305 (15)
C2—O4	1.222 (15)	C11—N4	1.354 (15)
C2—O5	1.271 (15)	C11—H11A	0.9300
C2—C4	1.510 (17)	C12—C13	1.323 (18)
C3—C5	1.36 (2)	C12—N1	1.379 (14)
C3—C4	1.540 (19)	C12—H12A	0.9300
C3—H3A	0.9800	C13—N2	1.357 (16)
C4—C6	1.38 (2)	C13—H13A	0.9300
C4—H4A	0.9800	C14—N1	1.306 (15)
C5—O1	1.47 (2)	C14—N2	1.304 (15)
C5—C7	1.67 (2)	C14—H14A	0.9300
C5—H5A	0.9800	N2—H2A	0.8600
C6—O1	1.476 (18)	N4—H4B	0.8600
C6—C8	1.57 (2)	O3—Cd1i	2.333 (8)
C6—H6A	0.9800	O4—Cd1iii	2.487 (8)
C7—C8	1.57 (2)	O5—Cd1iii	2.476 (7)
N1—Cd1—N3	174.2 (3)	C8—C6—H6A	112.5
N1—Cd1—O3i	93.7 (3)	C8—C7—C5	100.5 (13)
N3—Cd1—O3i	91.4 (3)	C8—C7—H7A	111.7
N1—Cd1—O5ii	89.6 (3)	C5—C7—H7A	111.7
N3—Cd1—O5ii	84.6 (3)	C8—C7—H7B	111.7
O3i—Cd1—O5ii	153.7 (3)	C5—C7—H7B	111.7
N1—Cd1—O4ii	90.2 (3)	H7A—C7—H7B	109.4
N3—Cd1—O4ii	85.8 (3)	C7—C8—C6	100.4 (12)
O3i—Cd1—O4ii	101.5 (3)	C7—C8—H8A	111.7
O5ii—Cd1—O4ii	52.3 (3)	C6—C8—H8A	111.7
N1—Cd1—O2	86.1 (3)	C7—C8—H8B	111.7
N3—Cd1—O2	94.2 (3)	C6—C8—H8B	111.7
O3i—Cd1—O2	117.3 (3)	H8A—C8—H8B	109.5
O5ii—Cd1—O2	89.0 (2)	C10—C9—N3	110.0 (12)
O4ii—Cd1—O2	141.1 (3)	C10—C9—H9A	125.0
N1—Cd1—O3	99.5 (3)	N3—C9—H9A	125.0
N3—Cd1—O3	85.1 (3)	N4—C10—C9	107.1 (11)
O3i—Cd1—O3	69.1 (4)	N4—C10—H10A	126.5
O5ii—Cd1—O3	136.0 (3)	C9—C10—H10A	126.5
O4ii—Cd1—O3	166.8 (3)	N3—C11—N4	110.6 (11)
O2—Cd1—O3	49.4 (3)	N3—C11—H11A	124.7
O2—C1—O3	118.3 (11)	N4—C11—H11A	124.7
O2—C1—C3	121.3 (13)	C13—C12—N1	107.8 (11)
O3—C1—C3	120.1 (13)	C13—C12—H12A	126.1
O4—C2—O5	122.5 (10)	N1—C12—H12A	126.1
O4—C2—C4	122.5 (13)	C12—C13—N2	107.9 (11)
O5—C2—C4	114.5 (12)	C12—C13—H13A	126.1
C5—C3—C1	117.4 (13)	N2—C13—H13A	126.1
C5—C3—C4	106.9 (13)	N1—C14—N2	111.8 (10)
C1—C3—C4	115.3 (11)	N1—C14—H14A	124.1
C5—C3—H3A	105.4	N2—C14—H14A	124.1
C1—C3—H3A	105.4	C14—N1—C12	105.7 (10)
C4—C3—H3A	105.4	C14—N1—Cd1	124.0 (7)
C6—C4—C2	122.0 (16)	C12—N1—Cd1	129.4 (8)
C6—C4—C3	100.0 (12)	C14—N2—C13	106.8 (10)
C2—C4—C3	119.0 (11)	C14—N2—H2A	126.6
C6—C4—H4A	104.6	C13—N2—H2A	126.6
C2—C4—H4A	104.6	C11—N3—C9	104.6 (10)
C3—C4—H4A	104.6	C11—N3—Cd1	123.6 (7)
C3—C5—O1	95.3 (13)	C9—N3—Cd1	131.1 (8)
C3—C5—C7	105.8 (14)	C10—N4—C11	107.7 (10)
O1—C5—C7	106.0 (12)	C10—N4—H4B	126.1
C3—C5—H5A	115.8	C11—N4—H4B	126.1
O1—C5—H5A	115.8	C6—O1—C5	95.3 (13)
C7—C5—H5A	115.8	C1—O2—Cd1	98.4 (7)
C4—C6—O1	99.4 (12)	C1—O3—Cd1i	149.9 (8)
C4—C6—C8	113.0 (16)	C1—O3—Cd1	92.7 (8)
O1—C6—C8	106.1 (13)	Cd1i—O3—Cd1	110.9 (4)
C4—C6—H6A	112.5	C2—O4—Cd1iii	92.6 (7)
O1—C6—H6A	112.5	C2—O5—Cd1iii	91.9 (6)
O2—C1—C3—C5	−67.4 (19)	C10—C9—N3—Cd1	−170.3 (9)
O3—C1—C3—C5	106.4 (18)	N1—Cd1—N3—C11	−105 (3)
O2—C1—C3—C4	60.1 (19)	O3i—Cd1—N3—C11	105.9 (9)
O3—C1—C3—C4	−126.2 (15)	O5ii—Cd1—N3—C11	−100.2 (9)
O4—C2—C4—C6	−15 (2)	O4ii—Cd1—N3—C11	−152.6 (9)
O5—C2—C4—C6	173.5 (13)	O2—Cd1—N3—C11	−11.6 (9)
O4—C2—C4—C3	−140.1 (15)	O3—Cd1—N3—C11	37.0 (9)
O5—C2—C4—C3	48 (2)	N1—Cd1—N3—C9	64 (3)
C5—C3—C4—C6	3.3 (19)	O3i—Cd1—N3—C9	−84.9 (10)
C1—C3—C4—C6	−129.2 (15)	O5ii—Cd1—N3—C9	69.0 (10)
C5—C3—C4—C2	138.9 (16)	O4ii—Cd1—N3—C9	16.6 (10)
C1—C3—C4—C2	6(2)	O2—Cd1—N3—C9	157.6 (10)
C1—C3—C5—O1	91.7 (15)	O3—Cd1—N3—C9	−153.8 (10)
C4—C3—C5—O1	−39.6 (16)	C9—C10—N4—C11	0.0 (15)
C1—C3—C5—C7	−160.0 (14)	N3—C11—N4—C10	0.2 (14)
C4—C3—C5—C7	68.7 (17)	C4—C6—O1—C5	−60.7 (15)
C2—C4—C6—O1	−99.0 (17)	C8—C6—O1—C5	56.7 (14)
C3—C4—C6—O1	34.8 (16)	C3—C5—O1—C6	60.4 (13)
C2—C4—C6—C8	149.0 (14)	C7—C5—O1—C6	−47.8 (13)
C3—C4—C6—C8	−77.2 (16)	O3—C1—O2—Cd1	−11.1 (12)
C3—C5—C7—C8	−76.9 (17)	C3—C1—O2—Cd1	162.8 (10)
O1—C5—C7—C8	23.5 (16)	N1—Cd1—O2—C1	−99.8 (7)
C5—C7—C8—C6	10.1 (16)	N3—Cd1—O2—C1	86.1 (7)
C4—C6—C8—C7	65.5 (17)	O3i—Cd1—O2—C1	−7.6 (8)
O1—C6—C8—C7	−42.4 (17)	O5ii—Cd1—O2—C1	170.6 (7)
N3—C9—C10—N4	−0.3 (15)	O4ii—Cd1—O2—C1	174.6 (7)
N1—C12—C13—N2	0.7 (14)	O3—Cd1—O2—C1	6.2 (7)
N2—C14—N1—C12	−0.4 (13)	O2—C1—O3—Cd1i	153.0 (13)
N2—C14—N1—Cd1	169.4 (8)	C3—C1—O3—Cd1i	−21 (2)
C13—C12—N1—C14	−0.2 (13)	O2—C1—O3—Cd1	10.5 (11)
C13—C12—N1—Cd1	−169.3 (8)	C3—C1—O3—Cd1	−163.4 (10)
N3—Cd1—N1—C14	−18 (3)	N1—Cd1—O3—C1	70.6 (7)
O3i—Cd1—N1—C14	131.6 (9)	N3—Cd1—O3—C1	−105.8 (7)
O5ii—Cd1—N1—C14	−22.2 (9)	O3i—Cd1—O3—C1	160.9 (9)
O4ii—Cd1—N1—C14	30.1 (9)	O5ii—Cd1—O3—C1	−28.7 (8)
O2—Cd1—N1—C14	−111.2 (9)	O4ii—Cd1—O3—C1	−152.6 (11)
O3—Cd1—N1—C14	−158.9 (9)	O2—Cd1—O3—C1	−6.0 (6)
N3—Cd1—N1—C12	150 (3)	N1—Cd1—O3—Cd1i	−90.3 (4)
O3i—Cd1—N1—C12	−61.1 (10)	N3—Cd1—O3—Cd1i	93.3 (4)
O5ii—Cd1—N1—C12	145.1 (9)	O3i—Cd1—O3—Cd1i	0.0
O4ii—Cd1—N1—C12	−162.7 (9)	O5ii—Cd1—O3—Cd1i	170.4 (3)
O2—Cd1—N1—C12	56.1 (9)	O4ii—Cd1—O3—Cd1i	46.5 (14)
O3—Cd1—N1—C12	8.4 (10)	O2—Cd1—O3—Cd1i	−166.9 (5)
N1—C14—N2—C13	0.8 (14)	O5—C2—O4—Cd1iii	9.0 (13)
C12—C13—N2—C14	−0.9 (14)	C4—C2—O4—Cd1iii	−162.4 (13)
N4—C11—N3—C9	−0.4 (13)	O4—C2—O5—Cd1iii	−9.0 (13)
N4—C11—N3—Cd1	171.2 (7)	C4—C2—O5—Cd1iii	163.0 (11)
C10—C9—N3—C11	0.4 (14)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O5iv	0.86	2.09	2.830 (12)	144
N4—H4B···O1iii	0.86	2.44	3.012 (17)	125
N4—H4B···O2iii	0.86	2.05	2.818 (13)	149
C6—H6A···O4	0.98	2.56	2.92 (2)	101
C11—H11A···O5	0.93	2.34	3.239 (15)	164
C14—H14A···O2ii	0.93	2.55	3.358 (15)	145
C12—H12A···Cg5i	0.93	2.76	3.565 (14)	145

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O5i	0.86	2.09	2.830 (12)	144
N4—H4B⋯O1ii	0.86	2.44	3.012 (17)	125
N4—H4B⋯O2ii	0.86	2.05	2.818 (13)	149
C6—H6A⋯O4	0.98	2.56	2.92 (2)	101
C11—H11A⋯O5	0.93	2.34	3.239 (15)	164
C14—H14A⋯O2iii	0.93	2.55	3.358 (15)	145
C12—H12A⋯Cg5iv	0.93	2.76	3.565 (14)	145

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) . Cg5 is the centroid of the N3/N4/C9–C11 ring.