Diaqua-bis-(2-chloro-benzoato-κO)bis-(nicotinamide-κN (1))cobalt(II).

In the title complex, [Co(C7H4ClO2)2(C6H6N2O)2(H2O)2], the Co(II) cation is located on an inversion center and is coord-inated by two 2-chloro-benzoate anions, two nicotin-amide (NA) ligands and two water mol-ecules. The four O atoms in the equatorial plane around the Co(II) cation form a slightly distorted square-planar arrangement, while the slightly distorted octa-hedral coordination is completed by the two pyridine N atoms of the NA ligands in the axial positions. The dihedral angle between the carboxyl-ate group and the adjacent benzene ring is 29.7 (4)°, while the pyridine and benzene rings are oriented at a dihedral angle of 83.17 (15)°. Intra-molecular O-H⋯O hydrogen bonding occurs between the carboxyl-ate group and coordinating water mol-ecule. In the crystal, inter-molecular N-H⋯O, O-H⋯O and weak C-H⋯O hydrogen bonds link the mol-ecules into a three-dimensional network.

Related literature

For background to niacin, see: Krishnamachari (1974 ▶). For information on the nicotinic acid derivative N,N-diethyl­nicotinamide, see: Bigoli et al. (1972 ▶). For related structures, see: Hökelek et al. (1996 ▶, 2009 ▶); Hökelek & Necefoğlu (1998 ▶, 2007 ▶); Necefoğlu et al. (2011 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

[Co(C7H4ClO2)2(C6H6N2O)2(H2O)2]

M = 650.32

Monoclinic,

a = 7.8679 (2) Å

b = 17.9522 (3) Å

c = 9.8492 (2) Å

β = 106.637 (3)°

V = 1332.92 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.90 mm−1

T = 100 K

0.39 × 0.33 × 0.23 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.708, T max = 0.811

10778 measured reflections

3285 independent reflections

2366 reflections with I > 2σ(I)

R int = 0.061

Refinement

R[F 2 > 2σ(F 2)] = 0.088

wR(F 2) = 0.237

S = 1.23

3285 reflections

202 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.42 e Å−3

Δρmin = −1.61 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, 2012 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶) and PLATON.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813004984/xu5678sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813004984/xu5678Isup2.hkl

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

[Co(C7H4ClO2)2(C6H6N2O)2(H2O)2]	F(000) = 666
Mr = 650.32	Dx = 1.620 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4735 reflections
a = 7.8679 (2) Å	θ = 2.4–27.9°
b = 17.9522 (3) Å	µ = 0.90 mm−1
c = 9.8492 (2) Å	T = 100 K
β = 106.637 (3)°	Block, pink
V = 1332.92 (5) Å3	0.39 × 0.33 × 0.23 mm
Z = 2

Bruker Kappa APEXII CCD area-detector diffractometer	3285 independent reflections
Radiation source: fine-focus sealed tube	2366 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.061
φ and ω scans	θmax = 28.3°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −6→10
Tmin = 0.708, Tmax = 0.811	k = −23→18
10778 measured reflections	l = −13→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)] = 0.088	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.237	H atoms treated by a mixture of independent and constrained refinement
S = 1.23	w = 1/[σ2(Fo2) + (0.0784P)2 + 7.9389P] where P = (Fo2 + 2Fc2)/3
3285 reflections	(Δ/σ)max < 0.001
202 parameters	Δρmax = 1.42 e Å−3
0 restraints	Δρmin = −1.61 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
Co1	0.0000	0.0000	0.0000	0.0169 (3)
Cl1	−0.0922 (2)	0.28811 (9)	−0.32577 (17)	0.0282 (4)
O1	−0.1130 (5)	0.1367 (2)	−0.2254 (4)	0.0223 (9)
O2	0.1155 (5)	0.0988 (2)	−0.0461 (4)	0.0192 (8)
O3	−0.4515 (5)	0.0095 (3)	0.3249 (4)	0.0250 (10)
O4	−0.2634 (6)	0.0436 (3)	−0.0890 (4)	0.0211 (9)
H41	−0.329 (12)	0.014 (5)	−0.133 (10)	0.04 (3)*
H42	−0.241 (11)	0.084 (5)	−0.146 (9)	0.05 (2)*
N1	−0.0041 (6)	0.0446 (3)	0.1993 (5)	0.0175 (10)
N2	−0.3567 (7)	0.0816 (3)	0.5201 (5)	0.0244 (12)
H21	−0.282 (12)	0.108 (5)	0.573 (10)	0.05 (3)*
H22	−0.457 (8)	0.071 (3)	0.543 (7)	0.013 (15)*
C1	0.0477 (7)	0.1383 (3)	−0.1558 (6)	0.0180 (11)
C2	0.1707 (8)	0.1857 (3)	−0.2106 (6)	0.0188 (11)
C3	0.1181 (8)	0.2488 (3)	−0.2961 (6)	0.0196 (11)
C4	0.2310 (8)	0.2848 (4)	−0.3596 (6)	0.0214 (12)
H4	0.1919	0.3263	−0.4166	0.026*
C5	0.4023 (8)	0.2589 (4)	−0.3380 (6)	0.0236 (12)
H5	0.4774	0.2818	−0.3830	0.028*
C6	0.4619 (8)	0.1984 (4)	−0.2485 (6)	0.0233 (12)
H6	0.5784	0.1821	−0.2303	0.028*
C7	0.3468 (8)	0.1629 (4)	−0.1870 (6)	0.0207 (12)
H7	0.3879	0.1224	−0.1278	0.025*
C8	−0.1512 (7)	0.0371 (3)	0.2405 (5)	0.0179 (11)
H8	−0.2469	0.0113	0.1819	0.021*
C9	−0.1672 (7)	0.0661 (3)	0.3663 (5)	0.0173 (11)
C10	−0.0260 (8)	0.1057 (3)	0.4526 (6)	0.0211 (12)
H10	−0.0339	0.1267	0.5369	0.025*
C11	0.1259 (8)	0.1134 (4)	0.4115 (6)	0.0227 (12)
H11	0.2225	0.1395	0.4680	0.027*
C12	0.1337 (7)	0.0817 (3)	0.2846 (5)	0.0189 (11)
H12	0.2375	0.0863	0.2581	0.023*
C13	−0.3372 (7)	0.0508 (3)	0.4019 (6)	0.0188 (12)

	U11	U22	U33	U12	U13	U23
Co1	0.0160 (5)	0.0304 (6)	0.0024 (4)	−0.0006 (4)	0.000	−0.0003 (4)
Cl1	0.0217 (7)	0.0377 (9)	0.0220 (8)	0.0073 (6)	0.0009 (6)	0.0057 (6)
O1	0.019 (2)	0.039 (3)	0.0062 (18)	−0.0013 (17)	−0.0009 (15)	0.0015 (17)
O2	0.0159 (19)	0.035 (2)	0.0026 (17)	−0.0021 (16)	−0.0033 (15)	0.0011 (15)
O3	0.019 (2)	0.047 (3)	0.0072 (18)	−0.0064 (18)	0.0008 (15)	−0.0044 (18)
O4	0.020 (2)	0.034 (3)	0.0059 (19)	−0.0020 (18)	−0.0014 (16)	−0.0009 (18)
N1	0.018 (2)	0.029 (3)	0.004 (2)	−0.0013 (19)	−0.0005 (17)	−0.0005 (18)
N2	0.019 (3)	0.049 (4)	0.007 (2)	−0.007 (2)	0.007 (2)	−0.006 (2)
C1	0.017 (2)	0.027 (3)	0.007 (2)	−0.001 (2)	−0.001 (2)	−0.003 (2)
C2	0.020 (3)	0.029 (3)	0.004 (2)	−0.004 (2)	−0.001 (2)	−0.003 (2)
C3	0.018 (3)	0.031 (3)	0.007 (2)	0.001 (2)	−0.001 (2)	−0.004 (2)
C4	0.021 (3)	0.032 (3)	0.007 (3)	−0.003 (2)	−0.002 (2)	−0.001 (2)
C5	0.024 (3)	0.038 (3)	0.008 (3)	−0.007 (3)	0.004 (2)	−0.002 (2)
C6	0.019 (3)	0.034 (3)	0.015 (3)	−0.002 (2)	0.001 (2)	−0.004 (2)
C7	0.018 (3)	0.031 (3)	0.008 (2)	−0.002 (2)	−0.004 (2)	−0.002 (2)
C8	0.016 (3)	0.030 (3)	0.004 (2)	−0.002 (2)	−0.002 (2)	−0.002 (2)
C9	0.014 (2)	0.030 (3)	0.006 (2)	0.002 (2)	0.001 (2)	0.002 (2)
C10	0.023 (3)	0.032 (3)	0.006 (2)	−0.003 (2)	0.001 (2)	−0.004 (2)
C11	0.018 (3)	0.036 (3)	0.008 (3)	−0.003 (2)	−0.006 (2)	−0.005 (2)
C12	0.015 (3)	0.035 (3)	0.005 (2)	0.000 (2)	0.000 (2)	0.002 (2)
C13	0.013 (2)	0.036 (3)	0.006 (2)	0.000 (2)	0.000 (2)	0.001 (2)

Co1—N1	2.129 (4)	C2—C7	1.399 (8)
Co1—N1i	2.129 (4)	C3—C4	1.384 (8)
Co1—O2	2.102 (4)	C4—C5	1.383 (8)
Co1—O2i	2.102 (4)	C4—H4	0.9300
Co1—O4	2.153 (4)	C5—H5	0.9300
Co1—O4i	2.153 (4)	C6—C5	1.392 (9)
Cl1—C3	1.744 (6)	C6—H6	0.9300
O1—C1	1.254 (7)	C7—C6	1.381 (8)
O2—C1	1.273 (7)	C7—H7	0.9300
O3—C13	1.243 (7)	C8—H8	0.9300
O4—H41	0.78 (9)	C9—C8	1.382 (7)
O4—H42	0.96 (9)	C9—C10	1.386 (8)
N1—C8	1.339 (7)	C9—C13	1.502 (7)
N1—C12	1.343 (7)	C10—C11	1.374 (8)
N2—C13	1.337 (7)	C10—H10	0.9300
N2—H21	0.81 (9)	C11—H11	0.9300
N2—H22	0.90 (6)	C12—C11	1.390 (8)
C1—C2	1.501 (8)	C12—H12	0.9300
C2—C3	1.402 (8)
O2—Co1—O2i	180.0 (2)	C4—C3—C2	122.1 (5)
O2—Co1—O4	91.75 (17)	C4—C3—Cl1	115.9 (5)
O2i—Co1—O4	88.25 (17)	C3—C4—H4	120.1
O2—Co1—O4i	88.25 (17)	C5—C4—C3	119.8 (6)
O2i—Co1—O4i	91.75 (17)	C5—C4—H4	120.1
O2—Co1—N1	90.19 (16)	C4—C5—C6	119.7 (5)
O2i—Co1—N1	89.81 (16)	C4—C5—H5	120.1
O2—Co1—N1i	89.81 (16)	C6—C5—H5	120.1
O2i—Co1—N1i	90.19 (16)	C5—C6—H6	120.2
O4—Co1—O4i	180.0 (2)	C7—C6—C5	119.6 (6)
N1—Co1—O4	88.39 (17)	C7—C6—H6	120.2
N1i—Co1—N1	180.0 (3)	C2—C7—H7	118.8
N1i—Co1—O4	91.61 (17)	C6—C7—C2	122.3 (6)
N1—Co1—O4i	91.61 (17)	C6—C7—H7	118.8
N1i—Co1—O4i	88.39 (17)	N1—C8—C9	122.8 (5)
C1—O2—Co1	123.4 (4)	N1—C8—H8	118.6
Co1—O4—H41	113 (6)	C9—C8—H8	118.6
Co1—O4—H42	101 (5)	C8—C9—C10	118.7 (5)
H41—O4—H42	113 (8)	C8—C9—C13	117.1 (5)
C8—N1—Co1	119.0 (4)	C10—C9—C13	124.1 (5)
C8—N1—C12	118.3 (5)	C9—C10—H10	120.6
C12—N1—Co1	122.8 (4)	C11—C10—C9	118.9 (5)
C13—N2—H21	124 (6)	C11—C10—H10	120.6
C13—N2—H22	117 (4)	C10—C11—C12	119.3 (5)
H22—N2—H21	119 (7)	C10—C11—H11	120.4
O1—C1—O2	124.2 (5)	C12—C11—H11	120.4
O1—C1—C2	118.0 (5)	N1—C12—C11	122.0 (5)
O2—C1—C2	117.6 (5)	N1—C12—H12	119.0
C3—C2—C1	124.4 (5)	C11—C12—H12	119.0
C7—C2—C1	119.0 (5)	O3—C13—N2	122.3 (5)
C7—C2—C3	116.4 (5)	O3—C13—C9	120.2 (5)
C2—C3—Cl1	122.0 (4)	N2—C13—C9	117.4 (5)
O4—Co1—O2—C1	−34.9 (4)	C1—C2—C3—Cl1	10.4 (8)
O4i—Co1—O2—C1	145.1 (4)	C1—C2—C3—C4	−171.1 (5)
N1—Co1—O2—C1	−123.3 (4)	C7—C2—C3—Cl1	−175.5 (4)
N1i—Co1—O2—C1	56.7 (4)	C7—C2—C3—C4	3.0 (8)
O2—Co1—N1—C8	134.5 (4)	C1—C2—C7—C6	171.9 (5)
O2i—Co1—N1—C8	−45.5 (4)	C3—C2—C7—C6	−2.5 (8)
O2—Co1—N1—C12	−43.9 (4)	Cl1—C3—C4—C5	177.9 (4)
O2i—Co1—N1—C12	136.1 (4)	C2—C3—C4—C5	−0.7 (9)
O4—Co1—N1—C8	42.8 (4)	C3—C4—C5—C6	−2.3 (9)
O4i—Co1—N1—C8	−137.2 (4)	C7—C6—C5—C4	2.7 (9)
O4—Co1—N1—C12	−135.6 (5)	C2—C7—C6—C5	−0.3 (9)
O4i—Co1—N1—C12	44.4 (5)	C10—C9—C8—N1	1.1 (9)
Co1—O2—C1—O1	21.7 (8)	C13—C9—C8—N1	−177.6 (5)
Co1—O2—C1—C2	−154.0 (4)	C8—C9—C10—C11	−1.3 (9)
Co1—N1—C8—C9	−178.2 (4)	C13—C9—C10—C11	177.2 (6)
C12—N1—C8—C9	0.3 (9)	C8—C9—C13—O3	4.8 (8)
Co1—N1—C12—C11	177.0 (4)	C8—C9—C13—N2	−176.9 (6)
C8—N1—C12—C11	−1.4 (8)	C10—C9—C13—O3	−173.8 (6)
O1—C1—C2—C3	26.3 (8)	C10—C9—C13—N2	4.5 (9)
O1—C1—C2—C7	−147.6 (5)	C9—C10—C11—C12	0.3 (9)
O2—C1—C2—C3	−157.8 (5)	N1—C12—C11—C10	1.1 (9)
O2—C1—C2—C7	28.3 (8)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H21···O1ii	0.82 (10)	2.11 (9)	2.861 (6)	152 (9)
N2—H22···O3iii	0.90 (7)	2.20 (6)	2.932 (7)	138 (5)
O4—H41···O3iv	0.78 (9)	2.20 (10)	2.890 (6)	147 (10)
O4—H42···O1	0.96 (9)	1.72 (9)	2.628 (7)	155 (8)
C6—H6···O1v	0.93	2.55	3.468 (8)	170
C10—H10···O1ii	0.93	2.60	3.476 (7)	158

Table 1

Selected bond lengths (Å)

Co1—N1	2.129 (4)
Co1—O2	2.102 (4)
Co1—O4	2.153 (4)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H21⋯O1i	0.82 (10)	2.11 (9)	2.861 (6)	152 (9)
N2—H22⋯O3ii	0.90 (7)	2.20 (6)	2.932 (7)	138 (5)
O4—H41⋯O3iii	0.78 (9)	2.20 (10)	2.890 (6)	147 (10)
O4—H42⋯O1	0.96 (9)	1.72 (9)	2.628 (7)	155 (8)
C6—H6⋯O1iv	0.93	2.55	3.468 (8)	170
C10—H10⋯O1i	0.93	2.60	3.476 (7)	158

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