Tetra-kis(μ-2-iodo-benzoato-κ(2)O:O')bis-[aqua-copper(II)].

In the centrosymmetric binuclear title complex, [Cu(2)(C(7)H(4)IO(2))(4)(H(2)O)(2)], the two Cu(II) ions [Cu⋯Cu = 2.6009 (5) Å] are bridged by four 2-iodo-benzoate (IB) ligands. The four nearest O atoms around each Cu(II) ion form a distorted square-planar arrangement, the distorted square-pyramidal coordination being completed by the O atom of the water mol-ecule at a distance of 2.1525 (16) Å. The dihedral angle between the benzene ring and the carboxyl-ate group is 25.67 (13)° in one of the independent IB ligands and 6.44 (11)° in the other. The benzene rings of the two independent IB ligands are oriented at a dihedral angle of 86.61 (7)°. In the crystal, O-H⋯O inter-actions link the mol-ecules into a two-dimensional network. π-π contacts between the benzene rings [centroid-centroid distances = 3.810 (2) and 3.838 (2) Å] may further stabilize the structure.

Related literature

For niacin, see: Krishnamachari (1974 ▶). For N,N-diethyl­nicotinamide, see: Bigoli et al. (1972 ▶). For related structures, see: Speier & Fulop (1989 ▶); Usubaliev et al. (1980 ▶); Hökelek et al. (1995 ▶, 2009a ▶,b ▶,c ▶, 2011 ▶); Necefoğlu et al. (2010a ▶,b ▶).

Experimental

Crystal data

[Cu2(C7H4IO2)4(H2O)2]

M = 1151.14

Triclinic,

a = 7.3563 (2) Å

b = 10.7448 (3) Å

c = 10.9066 (3) Å

α = 83.167 (3)°

β = 72.779 (2)°

γ = 77.227 (2)°

V = 801.73 (4) Å3

Z = 1

Mo Kα radiation

μ = 5.23 mm−1

T = 100 K

0.39 × 0.36 × 0.24 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.150, T max = 0.285

14335 measured reflections

3987 independent reflections

3818 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.019

wR(F 2) = 0.045

S = 1.16

3987 reflections

207 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.61 e Å−3

Δρmin = −0.66 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812010367/bq2345sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812010367/bq2345Isup2.hkl

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

[Cu2(C7H4IO2)4(H2O)2]	Z = 1
Mr = 1151.14	F(000) = 538
Triclinic, P1	Dx = 2.384 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.3563 (2) Å	Cell parameters from 9932 reflections
b = 10.7448 (3) Å	θ = 2.7–28.4°
c = 10.9066 (3) Å	µ = 5.23 mm−1
α = 83.167 (3)°	T = 100 K
β = 72.779 (2)°	Block, green
γ = 77.227 (2)°	0.39 × 0.36 × 0.24 mm
V = 801.73 (4) Å3

Bruker Kappa APEXII CCD area-detector diffractometer	3987 independent reflections
Radiation source: fine-focus sealed tube	3818 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
φ and ω scans	θmax = 28.4°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −9→9
Tmin = 0.150, Tmax = 0.285	k = −14→14
14335 measured reflections	l = −14→14

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)] = 0.019	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.045	H atoms treated by a mixture of independent and constrained refinement
S = 1.16	w = 1/[σ2(Fo2) + (0.0134P)2 + 0.9745P] where P = (Fo2 + 2Fc2)/3
3987 reflections	(Δ/σ)max = 0.002
207 parameters	Δρmax = 0.61 e Å−3
2 restraints	Δρmin = −0.66 e Å−3

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
I1	0.36263 (2)	0.882863 (16)	0.200310 (15)	0.01953 (5)
I2	−0.20180 (2)	0.701971 (15)	0.777993 (14)	0.01579 (5)
Cu1	0.65575 (4)	0.46820 (2)	0.53900 (2)	0.00769 (6)
O1	0.6886 (2)	0.64727 (16)	0.49086 (16)	0.0152 (3)
O2	0.4156 (2)	0.70018 (16)	0.43065 (16)	0.0153 (3)
O3	0.4755 (2)	0.52102 (17)	0.70398 (15)	0.0151 (3)
O4	0.7945 (2)	0.43067 (18)	0.35988 (15)	0.0171 (4)
O5	0.9024 (2)	0.41164 (17)	0.61507 (15)	0.0137 (3)
H51	1.010 (3)	0.375 (3)	0.573 (3)	0.031 (9)*
H52	0.920 (6)	0.462 (3)	0.660 (3)	0.050 (12)*
C1	0.5690 (3)	0.7241 (2)	0.4403 (2)	0.0111 (4)
C2	0.6219 (3)	0.8508 (2)	0.3878 (2)	0.0118 (4)
C3	0.5596 (3)	0.9249 (2)	0.2873 (2)	0.0137 (4)
C4	0.6304 (4)	1.0353 (2)	0.2372 (3)	0.0204 (5)
H4	0.5932	1.0828	0.1663	0.024*
C5	0.7553 (4)	1.0769 (3)	0.2899 (3)	0.0247 (6)
H5	0.8022	1.1529	0.2558	0.030*
C6	0.8112 (4)	1.0070 (2)	0.3925 (3)	0.0222 (5)
H6	0.8927	1.0367	0.4310	0.027*
C7	0.7483 (3)	0.8947 (2)	0.4384 (2)	0.0162 (5)
H7	0.7918	0.8456	0.5063	0.019*
C8	0.2958 (3)	0.5622 (2)	0.7233 (2)	0.0102 (4)
C9	0.1865 (3)	0.6078 (2)	0.8544 (2)	0.0095 (4)
C10	−0.0093 (3)	0.6684 (2)	0.8928 (2)	0.0115 (4)
C11	−0.0913 (3)	0.7150 (2)	1.0144 (2)	0.0170 (5)
H11	−0.2233	0.7576	1.0386	0.020*
C12	0.0184 (4)	0.6997 (3)	1.1009 (2)	0.0184 (5)
H12	−0.0385	0.7317	1.1841	0.022*
C13	0.2108 (4)	0.6377 (2)	1.0661 (2)	0.0160 (5)
H13	0.2860	0.6261	1.1255	0.019*
C14	0.2927 (3)	0.5930 (2)	0.9441 (2)	0.0124 (4)
H14	0.4251	0.5510	0.9206	0.015*

	U11	U22	U33	U12	U13	U23
I1	0.01733 (8)	0.02241 (9)	0.01989 (8)	−0.00265 (6)	−0.00902 (6)	0.00232 (6)
I2	0.01043 (8)	0.01989 (8)	0.01694 (7)	0.00135 (6)	−0.00594 (6)	−0.00335 (6)
Cu1	0.00592 (12)	0.00946 (13)	0.00725 (11)	−0.00149 (9)	−0.00117 (9)	−0.00054 (9)
O1	0.0129 (8)	0.0116 (8)	0.0231 (8)	−0.0056 (6)	−0.0079 (7)	0.0048 (6)
O2	0.0119 (8)	0.0115 (8)	0.0249 (8)	−0.0044 (6)	−0.0082 (7)	0.0022 (6)
O3	0.0092 (8)	0.0237 (9)	0.0101 (7)	0.0023 (7)	−0.0018 (6)	−0.0046 (6)
O4	0.0096 (8)	0.0315 (10)	0.0090 (7)	−0.0007 (7)	−0.0018 (6)	−0.0048 (7)
O5	0.0084 (8)	0.0194 (9)	0.0134 (7)	−0.0012 (7)	−0.0037 (6)	−0.0024 (6)
C1	0.0111 (10)	0.0123 (10)	0.0082 (9)	−0.0025 (8)	0.0004 (8)	−0.0016 (8)
C2	0.0088 (10)	0.0101 (10)	0.0146 (10)	−0.0011 (8)	−0.0006 (8)	−0.0009 (8)
C3	0.0089 (10)	0.0131 (11)	0.0166 (10)	−0.0003 (8)	−0.0009 (8)	−0.0010 (8)
C4	0.0148 (12)	0.0171 (12)	0.0252 (12)	−0.0012 (10)	−0.0040 (10)	0.0069 (10)
C5	0.0194 (13)	0.0147 (12)	0.0396 (15)	−0.0089 (10)	−0.0066 (11)	0.0069 (11)
C6	0.0179 (12)	0.0147 (12)	0.0365 (14)	−0.0071 (10)	−0.0095 (11)	0.0011 (10)
C7	0.0152 (11)	0.0136 (11)	0.0197 (11)	−0.0039 (9)	−0.0048 (9)	0.0007 (9)
C8	0.0118 (10)	0.0091 (10)	0.0097 (9)	−0.0040 (8)	−0.0021 (8)	0.0002 (7)
C9	0.0092 (10)	0.0087 (10)	0.0095 (9)	−0.0029 (8)	−0.0004 (8)	0.0001 (7)
C10	0.0099 (10)	0.0119 (10)	0.0129 (10)	−0.0016 (8)	−0.0042 (8)	0.0001 (8)
C11	0.0115 (11)	0.0206 (12)	0.0146 (11)	0.0017 (9)	0.0003 (9)	−0.0041 (9)
C12	0.0168 (12)	0.0238 (13)	0.0124 (10)	−0.0005 (10)	−0.0012 (9)	−0.0068 (9)
C13	0.0161 (12)	0.0197 (12)	0.0124 (10)	−0.0026 (9)	−0.0041 (9)	−0.0027 (9)
C14	0.0104 (10)	0.0134 (11)	0.0129 (10)	−0.0006 (8)	−0.0036 (8)	−0.0006 (8)

I1—C3	2.100 (2)	C4—H4	0.9500
I2—C10	2.102 (2)	C5—C4	1.388 (4)
Cu1—Cu1i	2.6009 (5)	C5—H5	0.9500
Cu1—O1	1.9814 (16)	C6—C5	1.386 (4)
Cu1—O2i	1.9577 (16)	C6—H6	0.9500
Cu1—O3	1.9533 (16)	C7—C6	1.374 (3)
Cu1—O4	1.9610 (16)	C7—H7	0.9500
Cu1—O5	2.1525 (16)	C8—O4i	1.260 (3)
O1—C1	1.272 (3)	C8—C9	1.498 (3)
O2—Cu1i	1.9577 (16)	C9—C10	1.403 (3)
O2—C1	1.247 (3)	C9—C14	1.397 (3)
O3—C8	1.260 (3)	C10—C11	1.388 (3)
O4—C8i	1.260 (3)	C11—C12	1.387 (3)
O5—H51	0.828 (18)	C11—H11	0.9500
O5—H52	0.828 (19)	C12—C13	1.384 (3)
C2—C1	1.499 (3)	C12—H12	0.9500
C2—C7	1.397 (3)	C13—C14	1.384 (3)
C3—C2	1.404 (3)	C13—H13	0.9500
C3—C4	1.389 (3)	C14—H14	0.9500
O1—Cu1—Cu1i	86.36 (5)	C5—C4—C3	120.5 (2)
O1—Cu1—O5	95.68 (7)	C5—C4—H4	119.8
O2i—Cu1—Cu1i	82.79 (5)	C4—C5—H5	120.1
O2i—Cu1—O1	168.98 (7)	C6—C5—C4	119.8 (2)
O2i—Cu1—O4	90.09 (8)	C6—C5—H5	120.1
O2i—Cu1—O5	95.26 (7)	C5—C6—H6	120.1
O3—Cu1—Cu1i	83.11 (5)	C7—C6—C5	119.7 (2)
O3—Cu1—O1	89.93 (7)	C7—C6—H6	120.1
O3—Cu1—O2i	90.68 (7)	C2—C7—H7	119.1
O3—Cu1—O4	168.90 (7)	C6—C7—C2	121.7 (2)
O3—Cu1—O5	93.88 (6)	C6—C7—H7	119.1
O4—Cu1—Cu1i	86.00 (5)	O3—C8—O4i	124.6 (2)
O4—Cu1—O1	87.22 (8)	O3—C8—C9	116.33 (18)
O4—Cu1—O5	97.08 (7)	O4i—C8—C9	119.06 (19)
O5—Cu1—Cu1i	176.38 (5)	C10—C9—C8	125.79 (19)
C1—O1—Cu1	119.86 (14)	C14—C9—C8	116.50 (19)
C1—O2—Cu1i	125.63 (15)	C14—C9—C10	117.66 (19)
C8—O3—Cu1	124.96 (14)	C9—C10—I2	125.52 (16)
C8i—O4—Cu1	121.09 (15)	C11—C10—I2	113.88 (16)
Cu1—O5—H51	123 (2)	C11—C10—C9	120.6 (2)
Cu1—O5—H52	117 (3)	C10—C11—H11	119.8
H51—O5—H52	108 (4)	C12—C11—C10	120.3 (2)
O1—C1—C2	116.23 (19)	C12—C11—H11	119.8
O2—C1—O1	124.6 (2)	C11—C12—H12	120.0
O2—C1—C2	119.2 (2)	C13—C12—C11	120.1 (2)
C3—C2—C1	124.2 (2)	C13—C12—H12	120.0
C7—C2—C1	117.6 (2)	C12—C13—H13	120.3
C7—C2—C3	118.1 (2)	C14—C13—C12	119.4 (2)
C2—C3—I1	125.24 (17)	C14—C13—H13	120.3
C4—C3—I1	114.73 (17)	C9—C14—H14	119.0
C4—C3—C2	120.0 (2)	C13—C14—C9	121.9 (2)
C3—C4—H4	119.8	C13—C14—H14	119.0
Cu1i—Cu1—O1—C1	−2.22 (16)	C3—C2—C7—C6	0.1 (4)
O2i—Cu1—O1—C1	7.9 (5)	I1—C3—C2—C1	5.4 (3)
O3—Cu1—O1—C1	−85.32 (17)	I1—C3—C2—C7	−177.62 (17)
O4—Cu1—O1—C1	83.95 (17)	C4—C3—C2—C1	−174.1 (2)
O5—Cu1—O1—C1	−179.21 (16)	C4—C3—C2—C7	2.9 (3)
Cu1i—Cu1—O3—C8	0.27 (18)	I1—C3—C4—C5	177.2 (2)
O1—Cu1—O3—C8	86.62 (19)	C2—C3—C4—C5	−3.3 (4)
O2i—Cu1—O3—C8	−82.38 (19)	C6—C5—C4—C3	0.6 (4)
O4—Cu1—O3—C8	11.6 (5)	C7—C6—C5—C4	2.3 (4)
O5—Cu1—O3—C8	−177.70 (18)	C2—C7—C6—C5	−2.7 (4)
Cu1i—Cu1—O4—C8i	−4.82 (18)	O3—C8—C9—C10	173.4 (2)
O1—Cu1—O4—C8i	−91.37 (18)	O3—C8—C9—C14	−3.7 (3)
O2i—Cu1—O4—C8i	77.94 (18)	O4i—C8—C9—C10	−5.2 (3)
O3—Cu1—O4—C8i	−16.0 (5)	O4i—C8—C9—C14	177.7 (2)
O5—Cu1—O4—C8i	173.25 (18)	C8—C9—C10—C11	−175.2 (2)
Cu1—O1—C1—O2	8.5 (3)	C8—C9—C10—I2	3.2 (3)
Cu1—O1—C1—C2	−170.57 (14)	C14—C9—C10—I2	−179.69 (16)
Cu1i—O2—C1—O1	−11.8 (3)	C14—C9—C10—C11	1.9 (3)
Cu1i—O2—C1—C2	167.28 (15)	C8—C9—C14—C13	176.4 (2)
Cu1—O3—C8—O4i	3.5 (3)	C10—C9—C14—C13	−1.0 (3)
Cu1—O3—C8—C9	−175.06 (14)	I2—C10—C11—C12	179.93 (19)
C3—C2—C1—O1	153.2 (2)	C9—C10—C11—C12	−1.5 (4)
C3—C2—C1—O2	−25.9 (3)	C10—C11—C12—C13	0.1 (4)
C7—C2—C1—O1	−23.8 (3)	C11—C12—C13—C14	0.8 (4)
C7—C2—C1—O2	157.1 (2)	C12—C13—C14—C9	−0.4 (4)
C1—C2—C7—C6	177.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H51···O1ii	0.83 (3)	2.09 (3)	2.839 (2)	152 (3)
O5—H52···O4ii	0.83 (3)	2.56 (4)	3.171 (2)	132 (3)

Table 1

Selected bond lengths (Å)

Cu1—O1	1.9814 (16)
Cu1—O2i	1.9577 (16)
Cu1—O3	1.9533 (16)
Cu1—O4	1.9610 (16)

Symmetry code: (i) .

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H51⋯O1ii	0.83 (3)	2.09 (3)	2.839 (2)	152 (3)
O5—H52⋯O4ii	0.83 (3)	2.56 (4)	3.171 (2)	132 (3)

Symmetry code: (ii) .