catena-Poly[[aqua­(2-iodo­benzoato-κO)cobalt(II)]-μ-aqua-μ-2-iodo­benzoato-κ2O:O′]

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

doi:10.1107/S1600536812015115

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Pages m601-m602

doi:10.1107/S1600536812015115

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catena-Poly[[aqua(2-iodobenzoato-κO)cobalt(II)]-μ-aqua-μ-2-iodobenzoato-κ²O:O′]

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 29 March 2012; accepted 5 April 2012; online 18 April 2012)

The asymmetric unit of the polymeric title compound, [Co(C₇H₄IO₂)₂(H₂O)₂]_n, contains one Co^II cation, two iodobenzoate anions and two water molecules. One iodobenzoate anion and one water molecule bridge adjacent Co cations, forming a polymeric chain running along the a axis, while the other iodobenzoate anion and water molecule coordinate in a monodentate manner to the Co^II cation, completing the slightly distorted octahedral geometry. In the two independent anionic ligands, the carboxylate groups are twisted away from the attached benzene rings by 51.38 (18) and 39.89 (11)°, and the two benzene rings are nearly perpendicular to each other with a dihedral angle of 86.09 (10)°. Intramolecular O—H⋯O hydrogen bonds between coordinating water molecules and adjacent carboxylate O atoms help to stabilize the molecular structure. In the crystal, weak C—H⋯O hydrogen bonds link the polymeric chains into a three-dimentional supramolecular network.

Related literature

For niacin, see: Krishnamachari (1974 ) and for information on the nicotinic acid derivative N,N-diethylnicotinamide, see: Bigoli et al. (1972 ). For related structures, see: Hökelek et al. (2009 , 2010a ,b , 2011 ); Necefoğlu et al. (2011 ); Zaman et al. (2012 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

[Co(C₇H₄IO₂)₂(H₂O)₂]
M_r = 588.97
Orthorhombic, P 2₁ 2₁ 2₁
a = 7.5051 (3) Å
b = 10.5639 (4) Å
c = 21.6723 (9) Å
V = 1718.25 (12) Å³
Z = 4
Mo Kα radiation
μ = 4.62 mm⁻¹
T = 100 K
0.26 × 0.23 × 0.17 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.313, T_max = 0.456
30167 measured reflections
4313 independent reflections
4300 reflections with I > 2σ(I)
R_int = 0.037

Refinement

R[F² > 2σ(F²)] = 0.020
wR(F²) = 0.051
S = 1.20
4313 reflections
224 parameters
8 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.60 e Å⁻³
Δρ_min = −1.03 e Å⁻³
Absolute structure: Flack (1983 ), 1835 Friedel pairs
Flack parameter: 0.016 (19)

Table 1
Selected bond lengths (Å)

Co1—O2	2.118 (2)
Co1—O3ⁱ	2.021 (2)
Co1—O4	2.016 (2)
Co1—O5	2.124 (2)
Co1—O5ⁱ	2.151 (2)
Co1—O6	2.110 (2)
Symmetry code: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+2]$ .

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H51⋯O1ⁱⁱ	0.86 (3)	1.64 (3)	2.486 (3)	167 (5)
O6—H61⋯O2ⁱ	0.86 (2)	1.92 (2)	2.742 (3)	161 (4)
C4—H4⋯O1ⁱⁱⁱ	0.95	2.56	3.364 (4)	142
C13—H13⋯O4^iv	0.95	2.58	3.495 (4)	162
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+2]$ ; (ii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+2]$ ; (iii) $[-x+2, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iv) $[x-{\script{1\over 2}}, -y-{\script{1\over 2}}, -z+2]$ .

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/S1600536812015115/xu5504sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812015115/xu5504Isup2.hkl

checkCIF report

Comment top

As a part of our ongoing investigations of 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 asymmetric unit of the title compound, (I), contains one Co^II ion, two 2-iodobenzoate (IB) ligands and two water molecules (Fig. 1). In the crystal of the title compound, each Co^II ion is coordinated by one IB ligand, one water molecule, two symmetry related IB ligands and two symmetry related water molecules, while the symmetry related Co(II) ions are bridged by the two O atoms of the symmetry related IB ligands and the two O atoms of the two symmetry related water molecules forming a polymeric chain. The coordination around the Co(II) ion is a slightly distorted octahedral (Fig. 2).

The crystal structures of some benzoate containing polymeric complexes of Mn^II, Zn^II and Pb^II ions, [Mn₂(C₈H₇O₂)₄(C₁₀H₁₄N₂O)₂(H₂O)]_n (Hökelek et al., 2010a), [Mn(C₇H₄FO₂)₂(H₂O)₂]_n (Necefoğlu et al., 2011), [Zn(C₈H₅O₃)₂(C₆H₆N₂O)]_n (Hökelek et al., 2009), [Pb(C₈H₇O₂)₂(C₆H₆N₂O)]_n (Hökelek et al., 2010b), {[Pb(C₉H₉O₂)₂(C₆H₆N₂O)].H₂O}_n (Hökelek et al., 2011), {[Pb(C₇H₅O₃)₂(C₆H₆N₂O)].H₂O}_n (Zaman et al., 2012) have also been reported.

In the title compound, the four O atoms (O2, O3', O4 and O6) in the equatorial plane around the Co^II ion form a slightly distorted square-planar arrangement, while the slightly distorted octahedral coordination is completed by the two symmetry related O atoms of the water molecules (O5 and O5') in the axial positions. The near equalities of the C1—O1 [1.252 (4) Å], C1—O2 [1.267 (4) Å], C8—O3 [1.251 (4) Å] and C8—O4 [1.260 (4) Å] bonds in the carboxylate groups indicate delocalized bonding arrangement, rather than localized single and double bonds. The average Co—O bond lengths are 2.052 (2) Å (for benzoate oxygens) and 2.128 (2) Å (for water oxygens) (Table 1) close to standard values (Allen et al., 1987). The Co atom is displaced out of the mean-planes of the carboxylate groups (O1/C1/O2) and (O3/C8/O4) by -0.5163 (4) and 0.3155 (4) Å, respectively. The dihedral angles between the planar carboxylate groups (O1/C1/O2) and (O3/C8/O4) and the adjacent benzene rings A (C2—C7) and B (C9—C14) are 51.38 (18) and 39.89 (11) °, respectively. The benzene rings are oriented at a dihedral angle of A/B = 86.09 (10)°.

In the crystal, O-H···O and weak C-H···O hydrogen bonds (Table 2) link the molecules into a three-dimentional supramolecular network. A weak C-H···π interaction is also found in the crystal structure.

Related literature top

For niacin, see: Krishnamachari (1974) and for infomation on the nicotinic acid derivative N,N-diethylnicotinamide, see: Bigoli et al. (1972). For related structures, see: Hökelek et al. (2009, 2010a,b, 2011); Necefoğlu et al. (2011); Zaman et al. (2012). For bond-length data, see: Allen et al. (1987).

Experimental top

The title compound was prepared by the reaction of CoSO₄.7H₂O (1.41 g, 5 mmol) in H₂O (100 ml) with sodium 2-iodobenzoate (2.70 g, 10 mmol) in H₂O (50 ml) at room temperature. The mixture was filtered and set aside to crystallize at ambient temperature for one week, giving orange single crystals.

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 asymmetric unit of the title molecule with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Part of the polymeric chain of the title compound.

catena-Poly[[aqua(2-iodobenzoato-κO)cobalt(II)]- µ-aqua-µ-2-iodobenzoato-κ²O:O'] top

Crystal data top

[Co(C₇H₄IO₂)₂(H₂O)₂]	F(000) = 1108
M_r = 588.97	D_x = 2.277 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 9972 reflections
a = 7.5051 (3) Å	θ = 2.7–28.4°
b = 10.5639 (4) Å	µ = 4.62 mm⁻¹
c = 21.6723 (9) Å	T = 100 K
V = 1718.25 (12) Å³	Block, orange
Z = 4	0.26 × 0.23 × 0.17 mm

Data collection top

Bruker Kappa APEXII CCD area-detector diffractometer	4313 independent reflections
Radiation source: fine-focus sealed tube	4300 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.037
ϕ and ω scans	θ_max = 28.4°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −10→10
T_min = 0.313, T_max = 0.456	k = −13→14
30167 measured reflections	l = −29→28

Refinement top

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)] = 0.020	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.051	w = 1/[σ²(F_o²) + (0.0209P)² + 2.2878P] where P = (F_o² + 2F_c²)/3
S = 1.20	(Δ/σ)_max = 0.002
4313 reflections	Δρ_max = 0.60 e Å⁻³
224 parameters	Δρ_min = −1.03 e Å⁻³
8 restraints	Absolute structure: Flack (1983), 1835 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.016 (19)

Crystal data top

[Co(C₇H₄IO₂)₂(H₂O)₂]	V = 1718.25 (12) Å³
M_r = 588.97	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 7.5051 (3) Å	µ = 4.62 mm⁻¹
b = 10.5639 (4) Å	T = 100 K
c = 21.6723 (9) Å	0.26 × 0.23 × 0.17 mm

Data collection top

Bruker Kappa APEXII CCD area-detector diffractometer	4313 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	4300 reflections with I > 2σ(I)
T_min = 0.313, T_max = 0.456	R_int = 0.037
30167 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.020	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.051	Δρ_max = 0.60 e Å⁻³
S = 1.20	Δρ_min = −1.03 e Å⁻³
4313 reflections	Absolute structure: Flack (1983), 1835 Friedel pairs
224 parameters	Absolute structure parameter: 0.016 (19)
8 restraints

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	1.14075 (3)	0.58295 (2)	0.834432 (12)	0.02259 (6)
I2	0.86998 (3)	−0.04434 (2)	0.858655 (9)	0.01608 (6)
Co1	0.81243 (5)	0.25155 (4)	0.997594 (19)	0.00670 (8)
O1	1.0232 (3)	0.2952 (2)	0.86860 (10)	0.0128 (5)
O2	0.7492 (3)	0.3161 (2)	0.90771 (10)	0.0107 (4)
O3	0.4106 (3)	0.0744 (2)	0.98386 (11)	0.0136 (5)
O4	0.7100 (3)	0.0786 (2)	0.98080 (11)	0.0122 (4)
O5	0.5662 (3)	0.3202 (2)	1.03253 (11)	0.0093 (4)
H51	0.562 (7)	0.289 (4)	1.0690 (12)	0.030 (14)*
H52	0.561 (7)	0.4004 (18)	1.037 (2)	0.034 (14)*
O6	0.8845 (3)	0.1971 (2)	1.08789 (11)	0.0148 (5)
H61	0.993 (3)	0.190 (5)	1.100 (2)	0.021 (12)*
H62	0.824 (6)	0.151 (5)	1.113 (2)	0.048 (17)*
C1	0.8667 (5)	0.3361 (3)	0.86686 (13)	0.0104 (5)
C2	0.8126 (4)	0.4134 (3)	0.81193 (14)	0.0125 (6)
C3	0.9090 (5)	0.5170 (3)	0.79051 (15)	0.0161 (7)
C4	0.8484 (6)	0.5875 (4)	0.74032 (16)	0.0229 (8)
H4	0.9116	0.6607	0.7273	0.027*
C5	0.6959 (6)	0.5502 (5)	0.70965 (16)	0.0311 (10)
H5	0.6560	0.5967	0.6748	0.037*
C6	0.6007 (6)	0.4452 (5)	0.72940 (19)	0.0329 (10)
H6	0.4969	0.4192	0.7078	0.040*
C7	0.6571 (5)	0.3786 (4)	0.78044 (16)	0.0201 (7)
H7	0.5897	0.3082	0.7945	0.024*
C8	0.5602 (4)	0.0274 (3)	0.97274 (13)	0.0082 (5)
C9	0.5600 (4)	−0.1065 (3)	0.94894 (14)	0.0081 (5)
C10	0.6767 (4)	−0.1532 (3)	0.90444 (13)	0.0088 (6)
C11	0.6674 (4)	−0.2780 (3)	0.88547 (15)	0.0134 (6)
H11	0.7435	−0.3072	0.8535	0.016*
C12	0.5480 (5)	−0.3607 (3)	0.91279 (16)	0.0157 (7)
H12	0.5450	−0.4471	0.9006	0.019*
C13	0.4330 (5)	−0.3169 (3)	0.95795 (18)	0.0183 (7)
H13	0.3521	−0.3733	0.9774	0.022*
C14	0.4365 (5)	−0.1903 (3)	0.97459 (15)	0.0137 (6)
H14	0.3531	−0.1599	1.0040	0.016*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1	0.01863 (11)	0.01494 (11)	0.03419 (13)	−0.00281 (9)	0.00237 (10)	0.00476 (9)
I2	0.01887 (10)	0.01658 (10)	0.01281 (9)	−0.00775 (9)	0.00753 (8)	−0.00351 (8)
Co1	0.00702 (19)	0.00527 (16)	0.00782 (16)	−0.00060 (14)	−0.00006 (14)	−0.00093 (15)
O1	0.0111 (11)	0.0154 (11)	0.0118 (11)	0.0016 (9)	0.0016 (8)	0.0024 (9)
O2	0.0092 (11)	0.0128 (11)	0.0102 (10)	0.0004 (9)	0.0007 (8)	0.0018 (8)
O3	0.0117 (11)	0.0071 (10)	0.0221 (12)	0.0017 (8)	0.0011 (8)	−0.0025 (9)
O4	0.0091 (10)	0.0069 (10)	0.0208 (11)	−0.0004 (8)	0.0004 (9)	−0.0025 (9)
O5	0.0088 (10)	0.0056 (10)	0.0135 (11)	−0.0002 (8)	−0.0002 (8)	−0.0014 (8)
O6	0.0092 (11)	0.0205 (12)	0.0146 (11)	0.0002 (10)	−0.0005 (9)	0.0039 (9)
C1	0.0114 (13)	0.0107 (13)	0.0092 (13)	−0.0034 (12)	0.0005 (12)	−0.0020 (10)
C2	0.0144 (15)	0.0163 (15)	0.0067 (13)	0.0044 (12)	0.0008 (11)	−0.0022 (11)
C3	0.0202 (17)	0.0169 (17)	0.0111 (14)	0.0077 (13)	0.0059 (12)	0.0005 (12)
C4	0.032 (2)	0.0222 (17)	0.0145 (16)	0.0163 (17)	0.0104 (15)	0.0081 (13)
C5	0.039 (2)	0.044 (3)	0.0107 (15)	0.023 (2)	0.0014 (15)	0.0072 (16)
C6	0.028 (2)	0.053 (3)	0.0177 (17)	0.012 (2)	−0.0096 (15)	−0.0045 (19)
C7	0.0167 (17)	0.0296 (19)	0.0139 (15)	0.0014 (15)	−0.0035 (13)	−0.0010 (13)
C8	0.0106 (13)	0.0065 (14)	0.0075 (12)	0.0013 (11)	0.0005 (10)	0.0006 (10)
C9	0.0093 (13)	0.0054 (13)	0.0096 (13)	0.0005 (11)	−0.0006 (11)	−0.0011 (10)
C10	0.0101 (14)	0.0111 (15)	0.0052 (12)	−0.0006 (11)	0.0000 (10)	−0.0003 (10)
C11	0.0139 (16)	0.0139 (15)	0.0124 (14)	0.0004 (12)	0.0018 (12)	−0.0059 (11)
C12	0.0186 (17)	0.0083 (15)	0.0202 (16)	−0.0011 (13)	0.0010 (13)	−0.0066 (12)
C13	0.0198 (17)	0.0116 (16)	0.0235 (17)	−0.0066 (14)	0.0052 (14)	−0.0014 (13)
C14	0.0161 (15)	0.0118 (15)	0.0132 (14)	−0.0038 (13)	0.0063 (12)	−0.0041 (12)

Geometric parameters (Å, º) top

I1—C3	2.102 (4)	C3—C4	1.395 (5)
I2—C10	2.100 (3)	C4—C5	1.381 (7)
Co1—O2	2.118 (2)	C4—H4	0.9500
Co1—O3ⁱ	2.021 (2)	C5—C6	1.387 (7)
Co1—O4	2.016 (2)	C5—H5	0.9500
Co1—O5	2.124 (2)	C6—C7	1.377 (5)
Co1—O5ⁱ	2.151 (2)	C6—H6	0.9500
Co1—O6	2.110 (2)	C7—C2	1.400 (5)
O1—C1	1.252 (4)	C7—H7	0.9500
O2—C1	1.267 (4)	C8—C9	1.506 (4)
O3—Co1ⁱⁱ	2.021 (2)	C9—C10	1.393 (4)
O3—C8	1.251 (4)	C9—C14	1.397 (4)
O4—C8	1.260 (4)	C11—C10	1.382 (4)
O5—Co1ⁱⁱ	2.151 (2)	C11—H11	0.9500
O5—H51	0.855 (19)	C12—C11	1.385 (5)
O5—H52	0.855 (18)	C12—H12	0.9500
O6—H61	0.854 (18)	C13—C12	1.385 (5)
O6—H62	0.86 (2)	C13—H13	0.9500
C2—C1	1.499 (4)	C14—C13	1.385 (4)
C3—C2	1.392 (5)	C14—H14	0.9500

O2—Co1—O5	91.32 (9)	C4—C3—I1	116.5 (3)
O2—Co1—O5ⁱ	91.88 (9)	C5—C4—C3	119.5 (4)
O3ⁱ—Co1—O6	88.28 (10)	C5—C4—H4	120.2
O3ⁱ—Co1—O2	88.37 (10)	C3—C4—H4	120.2
O3ⁱ—Co1—O5	86.32 (9)	C4—C5—C6	120.5 (3)
O3ⁱ—Co1—O5ⁱ	93.32 (9)	C4—C5—H5	119.8
O4—Co1—O2	92.32 (9)	C6—C5—H5	119.8
O4—Co1—O3ⁱ	178.57 (10)	C7—C6—C5	119.8 (4)
O4—Co1—O5	92.41 (9)	C7—C6—H6	120.1
O4—Co1—O5ⁱ	87.92 (9)	C5—C6—H6	120.1
O4—Co1—O6	91.04 (10)	C6—C7—C2	120.9 (4)
O5—Co1—O5ⁱ	176.77 (4)	C6—C7—H7	119.5
O6—Co1—O2	176.58 (10)	C2—C7—H7	119.5
O6—Co1—O5	89.15 (9)	O3—C8—O4	127.2 (3)
O6—Co1—O5ⁱ	87.63 (9)	O3—C8—C9	116.0 (3)
C1—O2—Co1	122.7 (2)	O4—C8—C9	116.8 (3)
C8—O3—Co1ⁱⁱ	136.6 (2)	C10—C9—C8	124.7 (3)
C8—O4—Co1	139.0 (2)	C10—C9—C14	117.9 (3)
Co1—O5—Co1ⁱⁱ	122.81 (10)	C14—C9—C8	117.3 (3)
Co1—O5—H51	103 (3)	C9—C10—I2	124.6 (2)
Co1ⁱⁱ—O5—H51	97 (4)	C11—C10—I2	114.6 (2)
Co1—O5—H52	115 (4)	C11—C10—C9	120.8 (3)
Co1ⁱⁱ—O5—H52	110 (4)	C10—C11—C12	120.5 (3)
H51—O5—H52	106 (4)	C10—C11—H11	119.8
Co1—O6—H61	123 (3)	C12—C11—H11	119.8
Co1—O6—H62	127 (4)	C11—C12—H12	120.2
H61—O6—H62	106 (4)	C13—C12—C11	119.6 (3)
O1—C1—O2	125.1 (3)	C13—C12—H12	120.2
O1—C1—C2	117.8 (3)	C12—C13—H13	120.1
O2—C1—C2	117.2 (3)	C14—C13—C12	119.7 (3)
C3—C2—C1	123.5 (3)	C14—C13—H13	120.1
C3—C2—C7	118.5 (3)	C9—C14—H14	119.3
C7—C2—C1	118.0 (3)	C13—C14—C9	121.4 (3)
C2—C3—I1	122.7 (2)	C13—C14—H14	119.3
C2—C3—C4	120.7 (4)

O3ⁱ—Co1—O2—C1	72.6 (2)	C4—C3—C2—C1	−177.9 (3)
O4—Co1—O2—C1	−108.6 (2)	C4—C3—C2—C7	2.4 (5)
O5—Co1—O2—C1	158.9 (2)	I1—C3—C4—C5	−179.4 (3)
O5ⁱ—Co1—O2—C1	−20.6 (2)	C2—C3—C4—C5	−3.3 (5)
O2—Co1—O4—C8	−70.4 (3)	C3—C4—C5—C6	1.6 (6)
O5—Co1—O4—C8	21.0 (3)	C4—C5—C6—C7	0.9 (6)
O5ⁱ—Co1—O4—C8	−162.2 (3)	C5—C6—C7—C2	−1.7 (6)
O6—Co1—O4—C8	110.2 (3)	C6—C7—C2—C1	−179.6 (3)
O2—Co1—O5—Co1ⁱⁱ	63.36 (13)	C6—C7—C2—C3	0.1 (5)
O3ⁱ—Co1—O5—Co1ⁱⁱ	151.65 (14)	O3—C8—C9—C10	142.8 (3)
O4—Co1—O5—Co1ⁱⁱ	−29.01 (13)	O3—C8—C9—C14	−38.8 (4)
O6—Co1—O5—Co1ⁱⁱ	−120.02 (13)	O4—C8—C9—C10	−39.0 (4)
Co1—O2—C1—O1	16.8 (4)	O4—C8—C9—C14	139.4 (3)
Co1—O2—C1—C2	−164.0 (2)	C8—C9—C10—I2	−2.7 (4)
Co1ⁱⁱ—O3—C8—O4	14.0 (5)	C8—C9—C10—C11	179.7 (3)
Co1ⁱⁱ—O3—C8—C9	−168.0 (2)	C14—C9—C10—I2	178.9 (2)
Co1—O4—C8—O3	−13.8 (5)	C14—C9—C10—C11	1.4 (5)
Co1—O4—C8—C9	168.2 (2)	C8—C9—C14—C13	−176.5 (3)
C3—C2—C1—O1	−51.1 (4)	C10—C9—C14—C13	2.0 (5)
C3—C2—C1—O2	129.7 (3)	C12—C11—C10—I2	178.7 (3)
C7—C2—C1—O1	128.6 (3)	C12—C11—C10—C9	−3.5 (5)
C7—C2—C1—O2	−50.7 (4)	C13—C12—C11—C10	2.2 (5)
I1—C3—C2—C1	−2.0 (4)	C14—C13—C12—C11	1.1 (6)
I1—C3—C2—C7	178.3 (2)	C9—C14—C13—C12	−3.2 (6)

Symmetry codes: (i) x+1/2, −y+1/2, −z+2; (ii) x−1/2, −y+1/2, −z+2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H51···O1ⁱⁱ	0.86 (3)	1.64 (3)	2.486 (3)	167 (5)
O6—H61···O2ⁱ	0.86 (2)	1.92 (2)	2.742 (3)	161 (4)
C4—H4···O1ⁱⁱⁱ	0.95	2.56	3.364 (4)	142
C13—H13···O4^iv	0.95	2.58	3.495 (4)	162

Symmetry codes: (i) x+1/2, −y+1/2, −z+2; (ii) x−1/2, −y+1/2, −z+2; (iii) −x+2, y+1/2, −z+3/2; (iv) x−1/2, −y−1/2, −z+2.

Experimental details

Crystal data
Chemical formula	[Co(C₇H₄IO₂)₂(H₂O)₂]
M_r	588.97
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	100
a, b, c (Å)	7.5051 (3), 10.5639 (4), 21.6723 (9)
V (Å³)	1718.25 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	4.62
Crystal size (mm)	0.26 × 0.23 × 0.17

Data collection
Diffractometer	Bruker Kappa APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.313, 0.456
No. of measured, independent and observed [I > 2σ(I)] reflections	30167, 4313, 4300
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.670

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.020, 0.051, 1.20
No. of reflections	4313
No. of parameters	224
No. of restraints	8
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.60, −1.03
Absolute structure	Flack (1983), 1835 Friedel pairs
Absolute structure parameter	0.016 (19)

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

Co1—O2	2.118 (2)	Co1—O5	2.124 (2)
Co1—O3ⁱ	2.021 (2)	Co1—O5ⁱ	2.151 (2)
Co1—O4	2.016 (2)	Co1—O6	2.110 (2)

Symmetry code: (i) x+1/2, −y+1/2, −z+2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H51···O1ⁱⁱ	0.86 (3)	1.64 (3)	2.486 (3)	167 (5)
O6—H61···O2ⁱ	0.86 (2)	1.92 (2)	2.742 (3)	161 (4)
C4—H4···O1ⁱⁱⁱ	0.95	2.56	3.364 (4)	142
C13—H13···O4^iv	0.95	2.58	3.495 (4)	162

Symmetry codes: (i) x+1/2, −y+1/2, −z+2; (ii) x−1/2, −y+1/2, −z+2; (iii) −x+2, y+1/2, −z+3/2; (iv) x−1/2, −y−1/2, −z+2.

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.

References

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