Diaqua-bis-(2-iodo-benzoato-κO)bis-(nicotinamide-κN(1))copper(II).

In the title complex, [Cu(C(7)H(4)IO(2))(2)(C(6)H(6)N(2)O)(2)(H(2)O)(2)], the Cu(II) cation is located on an inversion center and is coordinated by two monodentate 2-iodo-benzoate (IB) anions, two nicotinamide (NA) ligands and two water mol-ecules in a distorted octa-hedral coordination geometry. The dihedral angle between the carboxyl-ate group and the adjacent benzene ring is 32.12 (14)°, while the pyridine ring and the benzene ring are oriented at a dihedral angle of 82.02 (5)°. The coordinating water mol-ecule links with the carboxyl-ate group via an intra-molecular O-H⋯O hydrogen bond. In the crystal, N-H⋯O, O-H⋯O and weak C-H⋯O hydrogen bonds link the mol-ecules into a three-dimensional supra-molecular network.

Related literature

For literature on niacin, see: Krishnamachari (1974 ▶). For information on the nicotinic acid derivative N,N-diethyl­nicotinamide, see: Bigoli et al. (1972 ▶). For related structures, see: Aydın et al. (2012 ▶); Hökelek et al. (2009 ▶); Necefoğlu et al. (2011 ▶); Sertçelik et al. (2012 ▶); Sertçelik et al. (2009 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

[Cu(C7H4IO2)2(C6H6N2O)2(H2O)2]

M = 837.85

Monoclinic,

a = 8.1617 (2) Å

b = 18.3365 (4) Å

c = 9.7047 (3) Å

β = 103.573 (3)°

V = 1411.81 (7) Å3

Z = 2

Mo Kα radiation

μ = 3.02 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 = 0.528, T max = 0.661

13216 measured reflections

3531 independent reflections

3337 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.021

wR(F 2) = 0.058

S = 1.13

3531 reflections

203 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.97 e Å−3

Δρmin = −0.50 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/S1600536812034587/xu5599sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812034587/xu5599Isup2.hkl

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

[Cu(C7H4IO2)2(C6H6N2O)2(H2O)2]	F(000) = 814
Mr = 837.85	Dx = 1.971 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 7325 reflections
a = 8.1617 (2) Å	θ = 2.8–28.3°
b = 18.3365 (4) Å	µ = 3.02 mm−1
c = 9.7047 (3) Å	T = 100 K
β = 103.573 (3)°	Block, blue
V = 1411.81 (7) Å3	0.39 × 0.36 × 0.24 mm
Z = 2

Bruker Kappa APEXII CCD area-detector diffractometer	3531 independent reflections
Radiation source: fine-focus sealed tube	3337 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.018
φ and ω scans	θmax = 28.4°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −10→10
Tmin = 0.528, Tmax = 0.661	k = −24→24
13216 measured reflections	l = −10→12

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)] = 0.021	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.058	H atoms treated by a mixture of independent and constrained refinement
S = 1.13	w = 1/[σ2(Fo2) + (0.0285P)2 + 1.437P] where P = (Fo2 + 2Fc2)/3
3531 reflections	(Δ/σ)max = 0.001
203 parameters	Δρmax = 0.97 e Å−3
0 restraints	Δρmin = −0.50 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
Cu1	0.0000	0.5000	0.0000	0.01102 (8)
I1	0.120179 (18)	0.213804 (8)	0.323774 (16)	0.02225 (6)
O1	−0.10863 (18)	0.40869 (8)	0.04600 (14)	0.0137 (3)
O2	0.10292 (18)	0.37645 (8)	0.22737 (15)	0.0163 (3)
O3	0.4441 (2)	0.48850 (9)	−0.32723 (15)	0.0195 (3)
O4	−0.2967 (2)	0.54420 (9)	−0.08965 (16)	0.0174 (3)
H41	−0.252 (5)	0.571 (2)	−0.145 (4)	0.045 (10)*
H42	−0.369 (5)	0.521 (2)	−0.140 (4)	0.056 (12)*
N1	0.0134 (2)	0.45775 (9)	−0.18686 (17)	0.0116 (3)
N2	0.3517 (2)	0.42184 (11)	−0.52508 (19)	0.0191 (4)
H21	0.434 (4)	0.4370 (16)	−0.555 (3)	0.024 (7)*
H22	0.276 (4)	0.3983 (16)	−0.578 (3)	0.026 (8)*
C1	−0.0459 (2)	0.37253 (10)	0.1582 (2)	0.0116 (3)
C2	−0.1668 (2)	0.32473 (11)	0.2144 (2)	0.0117 (3)
C3	−0.1182 (2)	0.26188 (11)	0.2949 (2)	0.0120 (3)
C4	−0.2309 (3)	0.22441 (11)	0.3571 (2)	0.0162 (4)
H4	−0.1958	0.1831	0.4116	0.019*
C5	−0.3955 (3)	0.24892 (12)	0.3375 (2)	0.0180 (4)
H5	−0.4703	0.2247	0.3807	0.022*
C6	−0.4487 (3)	0.30965 (12)	0.2535 (2)	0.0177 (4)
H6	−0.5599	0.3254	0.2382	0.021*
C7	−0.3354 (3)	0.34687 (11)	0.1925 (2)	0.0147 (4)
H7	−0.3722	0.3873	0.1359	0.018*
C8	0.1566 (2)	0.46254 (10)	−0.2307 (2)	0.0119 (4)
H8	0.2495	0.4847	−0.1717	0.014*
C9	0.1720 (2)	0.43569 (10)	−0.36104 (19)	0.0113 (3)
C10	0.0335 (3)	0.40108 (11)	−0.4471 (2)	0.0153 (4)
H10	0.0408	0.3815	−0.5338	0.018*
C11	−0.1159 (3)	0.39604 (12)	−0.4024 (2)	0.0164 (4)
H11	−0.2101	0.3733	−0.4585	0.020*
C12	−0.1209 (3)	0.42577 (11)	−0.2720 (2)	0.0142 (4)
H12	−0.2212	0.4235	−0.2424	0.017*
C13	0.3339 (3)	0.45019 (11)	−0.4031 (2)	0.0140 (4)

	U11	U22	U33	U12	U13	U23
Cu1	0.01365 (16)	0.01161 (15)	0.00929 (15)	−0.00216 (12)	0.00570 (12)	−0.00079 (11)
I1	0.01407 (8)	0.01936 (8)	0.03321 (10)	0.00596 (5)	0.00532 (6)	0.00443 (5)
O1	0.0148 (7)	0.0151 (7)	0.0114 (6)	−0.0026 (5)	0.0036 (5)	0.0004 (5)
O2	0.0112 (7)	0.0219 (7)	0.0152 (7)	−0.0038 (6)	0.0019 (5)	0.0012 (5)
O3	0.0158 (7)	0.0289 (8)	0.0142 (7)	−0.0075 (6)	0.0046 (6)	−0.0058 (6)
O4	0.0148 (7)	0.0222 (8)	0.0150 (7)	−0.0012 (6)	0.0028 (6)	0.0021 (6)
N1	0.0112 (8)	0.0128 (7)	0.0115 (7)	−0.0007 (6)	0.0044 (6)	0.0003 (6)
N2	0.0149 (9)	0.0301 (10)	0.0146 (8)	−0.0072 (8)	0.0082 (7)	−0.0074 (7)
C1	0.0119 (9)	0.0124 (8)	0.0112 (8)	−0.0013 (7)	0.0042 (7)	−0.0025 (6)
C2	0.0115 (9)	0.0128 (8)	0.0115 (8)	−0.0014 (7)	0.0041 (7)	−0.0010 (6)
C3	0.0088 (9)	0.0132 (8)	0.0139 (9)	0.0005 (7)	0.0020 (7)	−0.0011 (7)
C4	0.0185 (10)	0.0138 (9)	0.0163 (9)	−0.0032 (8)	0.0042 (8)	0.0020 (7)
C5	0.0153 (10)	0.0195 (10)	0.0211 (10)	−0.0053 (8)	0.0083 (8)	0.0003 (8)
C6	0.0111 (9)	0.0190 (10)	0.0235 (10)	0.0000 (8)	0.0052 (8)	−0.0006 (8)
C7	0.0142 (9)	0.0136 (9)	0.0160 (9)	0.0006 (7)	0.0030 (7)	0.0008 (7)
C8	0.0113 (9)	0.0135 (9)	0.0113 (8)	−0.0013 (7)	0.0037 (7)	−0.0001 (7)
C9	0.0103 (8)	0.0136 (8)	0.0109 (8)	−0.0011 (7)	0.0044 (7)	0.0002 (6)
C10	0.0148 (10)	0.0195 (10)	0.0121 (9)	−0.0026 (8)	0.0039 (7)	−0.0033 (7)
C11	0.0138 (9)	0.0202 (10)	0.0150 (9)	−0.0058 (8)	0.0028 (7)	−0.0037 (7)
C12	0.0129 (9)	0.0150 (9)	0.0158 (9)	−0.0026 (7)	0.0053 (7)	−0.0008 (7)
C13	0.0111 (9)	0.0183 (9)	0.0128 (9)	−0.0006 (7)	0.0033 (7)	0.0002 (7)

Cu1—O1	1.9937 (14)	C3—C2	1.397 (3)
Cu1—O1i	1.9937 (14)	C4—C3	1.394 (3)
Cu1—O4	2.5078 (16)	C4—C5	1.387 (3)
Cu1—O4i	2.5078 (16)	C4—H4	0.9300
Cu1—N1	1.9984 (16)	C5—C6	1.388 (3)
Cu1—N1i	1.9984 (16)	C5—H5	0.9300
I1—C3	2.0942 (19)	C6—H6	0.9300
O1—C1	1.275 (2)	C7—C6	1.389 (3)
O2—C1	1.245 (2)	C7—H7	0.9300
O3—C13	1.238 (3)	C8—H8	0.9300
O4—H41	0.87 (4)	C9—C8	1.390 (2)
O4—H42	0.80 (4)	C9—C10	1.391 (3)
N1—C8	1.337 (2)	C9—C13	1.496 (3)
N1—C12	1.343 (3)	C10—C11	1.390 (3)
N2—C13	1.331 (3)	C10—H10	0.9300
N2—H22	0.83 (3)	C11—H11	0.9300
N2—H21	0.84 (3)	C12—C11	1.387 (3)
C1—C2	1.513 (3)	C12—H12	0.9300
C2—C7	1.403 (3)
O1i—Cu1—O1	180.00 (7)	C4—C5—C6	119.99 (19)
O1—Cu1—N1	89.98 (6)	C4—C5—H5	120.0
O1i—Cu1—N1	90.02 (6)	C6—C5—H5	120.0
O1—Cu1—N1i	90.02 (6)	C5—C6—C7	119.8 (2)
O1i—Cu1—N1i	89.98 (6)	C5—C6—H6	120.1
O4—Cu1—O1	84.56 (6)	C7—C6—H6	120.1
O4—Cu1—N1	93.70 (6)	C2—C7—H7	119.3
N1—Cu1—N1i	180.00 (9)	C6—C7—C2	121.42 (19)
H41—O4—H42	106 (4)	C6—C7—H7	119.3
C1—O1—Cu1	121.16 (13)	N1—C8—C9	122.62 (18)
C8—N1—Cu1	120.11 (13)	N1—C8—H8	118.7
C12—N1—Cu1	121.13 (13)	C9—C8—H8	118.7
C8—N1—C12	118.74 (16)	C8—C9—C10	118.26 (18)
C13—N2—H21	116 (2)	C8—C9—C13	117.39 (17)
C13—N2—H22	122 (2)	C10—C9—C13	124.23 (17)
H22—N2—H21	120 (3)	C9—C10—H10	120.3
O1—C1—C2	116.35 (17)	C11—C10—C9	119.46 (18)
O2—C1—O1	125.16 (18)	C11—C10—H10	120.3
O2—C1—C2	118.39 (17)	C10—C11—H11	120.8
C3—C2—C1	123.79 (18)	C12—C11—C10	118.33 (19)
C3—C2—C7	117.57 (18)	C12—C11—H11	120.8
C7—C2—C1	118.51 (17)	N1—C12—C11	122.56 (19)
C2—C3—I1	123.71 (14)	N1—C12—H12	118.7
C4—C3—I1	114.92 (15)	C11—C12—H12	118.7
C4—C3—C2	121.30 (18)	O3—C13—N2	122.34 (19)
C3—C4—H4	120.1	O3—C13—C9	120.19 (17)
C5—C4—C3	119.83 (19)	N2—C13—C9	117.45 (18)
C5—C4—H4	120.1
N1—Cu1—O1—C1	123.90 (15)	I1—C3—C2—C7	173.86 (14)
N1i—Cu1—O1—C1	−56.10 (15)	C4—C3—C2—C1	172.78 (18)
O1—Cu1—N1—C8	−133.41 (15)	C4—C3—C2—C7	−3.0 (3)
O1i—Cu1—N1—C8	46.59 (15)	C5—C4—C3—I1	−176.15 (16)
O1—Cu1—N1—C12	48.21 (16)	C5—C4—C3—C2	1.0 (3)
O1i—Cu1—N1—C12	−131.79 (16)	C3—C4—C5—C6	1.5 (3)
Cu1—O1—C1—O2	−20.6 (3)	C4—C5—C6—C7	−1.8 (3)
Cu1—O1—C1—C2	155.73 (13)	C2—C7—C6—C5	−0.4 (3)
Cu1—N1—C8—C9	−178.46 (15)	C10—C9—C8—N1	−1.5 (3)
C12—N1—C8—C9	0.0 (3)	C13—C9—C8—N1	174.79 (18)
Cu1—N1—C12—C11	179.89 (16)	C8—C9—C10—C11	1.6 (3)
C8—N1—C12—C11	1.5 (3)	C13—C9—C10—C11	−174.41 (19)
O1—C1—C2—C3	153.14 (18)	C8—C9—C13—O3	−4.3 (3)
O1—C1—C2—C7	−31.1 (3)	C8—C9—C13—N2	177.18 (19)
O2—C1—C2—C3	−30.3 (3)	C10—C9—C13—O3	171.8 (2)
O2—C1—C2—C7	145.49 (19)	C10—C9—C13—N2	−6.8 (3)
C1—C2—C7—C6	−173.32 (18)	C9—C10—C11—C12	−0.3 (3)
C3—C2—C7—C6	2.7 (3)	N1—C12—C11—C10	−1.3 (3)
I1—C3—C2—C1	−10.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H21···O3ii	0.84 (3)	2.17 (3)	2.942 (3)	154 (3)
N2—H22···O2iii	0.83 (3)	2.11 (3)	2.881 (2)	154 (3)
O4—H41···O2i	0.87 (4)	1.87 (4)	2.720 (2)	165 (4)
O4—H42···O3iv	0.80 (4)	2.16 (4)	2.923 (2)	160 (4)
C10—H10···O2iii	0.93	2.49	3.368 (2)	158

Table 1

Selected bond lengths (Å)

Cu1—O1	1.9937 (14)
Cu1—O4	2.5078 (16)
Cu1—N1	1.9984 (16)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H21⋯O3i	0.84 (3)	2.17 (3)	2.942 (3)	154 (3)
N2—H22⋯O2ii	0.83 (3)	2.11 (3)	2.881 (2)	154 (3)
O4—H41⋯O2iii	0.87 (4)	1.87 (4)	2.720 (2)	165 (4)
O4—H42⋯O3iv	0.80 (4)	2.16 (4)	2.923 (2)	160 (4)
C10—H10⋯O2ii	0.93	2.49	3.368 (2)	158

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .