Tetra­kis(μ-2-iodo­benzoato-κ2O:O′)bis­[aqua­copper(II)]

Aydın, Ö.; Çaylak Delibaş, N.; Necefoğlu, H.; Hökelek, T.

doi:10.1107/S1600536812010367

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 4| April 2012| Pages m409-m410

doi:10.1107/S1600536812010367

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Tetrakis(μ-2-iodobenzoato-κ²O:O′)bis[aquacopper(II)]

Ömür Aydın,^a Nagihan Çaylak Delibaş,^b Hacali Necefoğlu ^a and Tuncer Hökelek ^c ^*

^aDepartment of Chemistry, Kafkas University, 36100 Kars, Turkey, ^bDepartment of Physics, Sakarya University, 54187 Esentepe, Sakarya, Turkey, and ^cDepartment of Physics, Hacettepe University, 06800 Beytepe, Ankara, Turkey
^*Correspondence e-mail: merzifon@hacettepe.edu.tr

(Received 7 March 2012; accepted 8 March 2012; online 14 March 2012)

In the centrosymmetric binuclear title complex, [Cu₂(C₇H₄IO₂)₄(H₂O)₂], the two Cu^II ions [Cu⋯Cu = 2.6009 (5) Å] are bridged by four 2-iodobenzoate (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 molecule at a distance of 2.1525 (16) Å. The dihedral angle between the benzene ring and the carboxylate 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 interactions link the molecules 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_r = 1151.14
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.019
wR(F²) = 0.045
S = 1.16
3987 reflections
207 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.61 e Å⁻³
Δρ_min = −0.66 e Å⁻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) -x+1, -y+1, -z+1.

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) -x+2, -y+1, -z+1.

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 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812010367/bq2345sup1.cif

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

checkCIF report

Comment top

As a part of our ongoing investigation on transition metal complexes of nicotinamide (NA), one form of niacin (Krishnamachari, 1974), and/or the nicotinic acid derivative N,N-diethylnicotinamide (DENA), an important respiratory stimulant (Bigoli et al., 1972), the title compound was synthesized and its crystal structure is reported herein.

The title compound is a binuclear compound, consisting of four iodobenzoate (IB) ligands. The structures of similar complexes of the Cu²⁺, Zn²⁺ and Co²⁺ ions, [Cu(C₆H₅COO)₂(C₅H₅N)]₂ (Usubaliev et al., 1980); [Cu(C₆H₅CO₂)₂(Py)]₂ (Speier & Fulop, 1989); [Cu₂(C₆H₅COO)₄(C₁₀H₁₄N₂O)₂] (Hökelek et al., 1995) [Cu₂(C₈H₇O₂)₄(C₆H₆N₂O)₂] (Necefoğlu et al., 2010a) [Zn₂(C₁₁H₁₄NO₂)₄(C₁₀H₁₄N₂O)₂] (Hökelek et al., 2009a); [Zn₂(C₈H₈NO₂)₄(C₁₀H₁₄N₂O)₂].2H₂O (Hökelek et al., 2009b); [Zn₂(C₉H₁₀NO₂)₄(C₁₀H₁₄N₂O)₂] (Hökelek et al., 2009c); [Zn₂(C₈H₇O₂)₄(C₁₀H₁₄N₂O)₂] (Necefoğlu et al., 2010b) and [Co₂(C₁₁H₁₄NO₂)₄(C₁₀H₁₄N₂O)₂] (Hökelek et al., 2011) have also been determined. In these structures, the benzoate ion acts as a bidentate ligand.

The title dimeric complex, [Cu₂(IB)₄(H₂O)₂], has a centre of symmetry and two Cu^II atoms are surrounded by four IB groups and two water molecules. The IB groups act as bridging ligands. The Cu···Cu' distance is 2.6009 (5) Å. The average Cu-O distance is 2.0012 (16) Å (Table 1), and four O atoms of the bridging IB ligands around each Cu atom form a distorted square plane. The Cu atom lies 0.1869 (3) Å below the least-squares plane. The average O-Cu-O bond angle is 92.48 (7)°. A distorted square-pyramidal arrangement around each Cu atom is completed by the water O atom at 2.1525 (16) Å from the Cu atom (Table 1). The O5-Cu1···Cu1' angle is 176.38 (5)° and the dihedral angle between plane through Cu1, O1, O2, C1, Cu1', O1', O2', C1' and the plane through Cu1, O3, O4, C8, Cu1', O3', O4', C8' is 89.13 (6)°. The dihedral angles between the planar carboxylate groups [(O1/O2/C1) and (O3/O4/C8)] and the adjacent benzene rings A (C2-C7) and B (C9-C14) are 25.67 (13) and 6.44 (11) °, respectively, while that between rings A and B is A/B = 86.61 (7)°.

In the crystal structure, intermolecular O-H···O interactions (Table 2) link the molecules into a two-dimensional network, in which they may be effective in the stabilization of the structure. The π–π contacts between the benzene rings, Cg1—Cg1ⁱ and Cg2—Cg2ⁱⁱ [symmetry codes: (i) 1 - x, -y, 1 - z, (ii) 2 - x, 1 - y, -z, where Cg1 and Cg2 are the centroids of the rings A (C2-C7) and B (C9-C14), respectively] may further stabilize the structure, with centroid-centroid distances of 3.810 (2) and 3.838 (2) Å].

Related literature top

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 top

The title compound was prepared by the reaction of CuSO₄.5H₂O (1.25 g, 5 mmol) in H₂O (100 ml) with sodium 2-iodobenzoate (2.70 g, 10 mmol) in H₂O (50 ml). The mixture was set aside to crystallize at ambient temperature for one day, giving green single crystals.

Structure description top

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).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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).

Figures top

Fig. 1. The molecular structure of the title compound with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. Primed atoms are generated by the symmetry operator:(') - x, - y, - z.

Tetrakis(µ-2-iodobenzoato-κ²O:O')bis[aquacopper(II)] top

Crystal data top

[Cu₂(C₇H₄IO₂)₄(H₂O)₂]	Z = 1
M_r = 1151.14	F(000) = 538
Triclinic, P1	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0134P)² + 0.9745P] where P = (F_o² + 2F_c²)/3
3987 reflections	(Δ/σ)_max = 0.002
207 parameters	Δρ_max = 0.61 e Å⁻³
2 restraints	Δρ_min = −0.66 e Å⁻³

Crystal data top

[Cu₂(C₇H₄IO₂)₄(H₂O)₂]	γ = 77.227 (2)°
M_r = 1151.14	V = 801.73 (4) Å³
Triclinic, P1	Z = 1
a = 7.3563 (2) Å	Mo Kα radiation
b = 10.7448 (3) Å	µ = 5.23 mm⁻¹
c = 10.9066 (3) Å	T = 100 K
α = 83.167 (3)°	0.39 × 0.36 × 0.24 mm
β = 72.779 (2)°

Data collection top

Bruker Kappa APEXII CCD area-detector diffractometer	3987 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	3818 reflections with I > 2σ(I)
T_min = 0.150, T_max = 0.285	R_int = 0.025
14335 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.019	2 restraints
wR(F²) = 0.045	H atoms treated by a mixture of independent and constrained refinement
S = 1.16	Δρ_max = 0.61 e Å⁻³
3987 reflections	Δρ_min = −0.66 e Å⁻³
207 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

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) −x+2, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	[Cu₂(C₇H₄IO₂)₄(H₂O)₂]
M_r	1151.14
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	7.3563 (2), 10.7448 (3), 10.9066 (3)
α, β, γ (°)	83.167 (3), 72.779 (2), 77.227 (2)
V (Å³)	801.73 (4)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	5.23
Crystal size (mm)	0.39 × 0.36 × 0.24

Data collection
Diffractometer	Bruker Kappa APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.150, 0.285
No. of measured, independent and observed [I > 2σ(I)] reflections	14335, 3987, 3818
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.669

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.019, 0.045, 1.16
No. of reflections	3987
No. of parameters	207
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.61, −0.66

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Selected bond lengths (Å) top

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

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

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) −x+2, −y+1, −z+1.

Acknowledgements

The authors are indebted to Anadolu University and the Medicinal Plants and Medicine Research Centre of Anadolu University, Eskişehir, Turkey, for the use of X-ray diffractometer.

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