Diaqua-bis-(2-bromo-benzoato-κO)bis-(N,N-diethyl-nicotinamide-κN)cobalt(II).

In the mononuclear title compound, [Co(C(7)H(4)BrO(2))(2)(C(10)H(14)N(2)O)(2)(H(2)O)(2)], the Co(II) ion is located on a crystallographic inversion center. The asymmetric unit is completed by one 2-bromo-benzoate anion, one diethyl-nicotinamide (DENA) ligand and one coordinated water mol-ecule; all ligands are monodentate. The four O atoms in the equatorial plane around Co(II) form a slightly distorted square-planar arrangement, while the slightly distorted octa-hedral coordination is completed by the two pyridine N atoms of the DENA ligands in axial positions. The dihedral angle between the carboxyl-ate group and the attached benzene ring is 84.7 (1)°; the pyridine and benzene rings are oriented at a dihedral angle of 43.64 (6)°. In the crystal structure, inter-molecular O-H⋯O and C-H⋯O hydrogen bonds link the mol-ecules into a three-dimensional network.

Related literature

For niacin, see: Krishnamachari (1974 ▶). For N,N-diethyl­nicotinamide, see: Bigoli et al. (1972 ▶). For related structures, see: Hökelek, Dal, Tercan, Aybirdi et al. (2009 ▶); Hökelek et al. (2009a ▶,b ▶,c ▶,d ▶,e ▶); Necefoğlu et al. (2010 ▶).

Experimental

Crystal data

[Co(C7H4BrO2)2(C10H14N2O)2(H2O)2]

M = 851.43

Monoclinic,

a = 13.0106 (2) Å

b = 10.3513 (2) Å

c = 14.9580 (3) Å

β = 114.311 (1)°

V = 1835.86 (6) Å3

Z = 2

Mo Kα radiation

μ = 2.70 mm−1

T = 100 K

0.31 × 0.28 × 0.23 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.489, T max = 0.576

16787 measured reflections

4528 independent reflections

3700 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.064

S = 1.04

4528 reflections

233 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.60 e Å−3

Δρmin = −0.32 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAIn class="Chemical">NT; 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 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810032630/im2218sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810032630/im2218Isup2.hkl

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

[Co(C7H4BrO2)2(C10H14N2O)2(H2O)2]	F(000) = 866
Mr = 851.43	Dx = 1.540 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6465 reflections
a = 13.0106 (2) Å	θ = 2.5–28.3°
b = 10.3513 (2) Å	µ = 2.70 mm−1
c = 14.9580 (3) Å	T = 100 K
β = 114.311 (1)°	Block, pink
V = 1835.86 (6) Å3	0.31 × 0.28 × 0.23 mm
Z = 2

Bruker Kappa APEXII CCD area-detector diffractometer	4528 independent reflections
Radiation source: fine-focus sealed tube	3700 reflections with I > 2σ(I)
graphite	Rint = 0.029
φ and ω scans	θmax = 28.4°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −17→17
Tmin = 0.489, Tmax = 0.576	k = −13→13
16787 measured reflections	l = −19→17

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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.064	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0277P)2 + 0.7345P] where P = (Fo2 + 2Fc2)/3
4528 reflections	(Δ/σ)max < 0.001
233 parameters	Δρmax = 0.60 e Å−3
0 restraints	Δρmin = −0.32 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
Br1	0.178480 (15)	0.14223 (2)	0.071476 (14)	0.02693 (7)
Co1	0.5000	0.0000	0.0000	0.01023 (8)
O1	0.36578 (13)	−0.11744 (14)	0.13111 (11)	0.0287 (3)
H41	0.603 (2)	0.226 (3)	0.0534 (18)	0.037 (7)*
H42	0.6254 (19)	0.163 (2)	−0.0114 (19)	0.030 (7)*
O2	0.46952 (9)	0.04937 (13)	0.12000 (8)	0.0152 (3)
O3	0.93287 (10)	−0.11547 (13)	0.39609 (9)	0.0169 (3)
O4	0.61748 (10)	0.15516 (14)	0.03719 (10)	0.0142 (3)
N1	0.64001 (11)	−0.12268 (15)	0.09116 (10)	0.0132 (3)
N2	0.98258 (12)	0.00503 (16)	0.29417 (11)	0.0164 (3)
C1	0.40749 (14)	−0.00794 (18)	0.15390 (13)	0.0150 (4)
C2	0.38447 (14)	0.06833 (18)	0.22975 (13)	0.0158 (4)
C3	0.28874 (15)	0.1439 (2)	0.20361 (13)	0.0187 (4)
C4	0.27047 (16)	0.2238 (2)	0.27075 (15)	0.0247 (4)
H4	0.2063	0.2751	0.2512	0.030*
C5	0.34959 (17)	0.2251 (2)	0.36688 (15)	0.0275 (5)
H5	0.3394	0.2790	0.4123	0.033*
C6	0.44413 (16)	0.1466 (2)	0.39613 (15)	0.0264 (5)
H6	0.4958	0.1456	0.4614	0.032*
C7	0.46161 (15)	0.0693 (2)	0.32779 (14)	0.0217 (4)
H7	0.5256	0.0176	0.3476	0.026*
C8	0.72933 (13)	−0.07013 (18)	0.16504 (12)	0.0138 (4)
H8	0.7295	0.0185	0.1752	0.017*
C9	0.82096 (13)	−0.14176 (18)	0.22667 (12)	0.0129 (3)
C10	0.82087 (13)	−0.27504 (19)	0.21376 (12)	0.0153 (4)
H10	0.8800	−0.3260	0.2555	0.018*
C11	0.72976 (14)	−0.32932 (19)	0.13661 (13)	0.0164 (4)
H11	0.7275	−0.4177	0.1248	0.020*
C12	0.64230 (13)	−0.25033 (18)	0.07735 (13)	0.0156 (4)
H12	0.5822	−0.2878	0.0254	0.019*
C13	0.91718 (13)	−0.08168 (18)	0.31162 (12)	0.0132 (4)
C14	0.97403 (16)	0.0414 (2)	0.19635 (14)	0.0267 (5)
H14A	0.9242	−0.0188	0.1483	0.032*
H14B	1.0479	0.0345	0.1954	0.032*
C15	0.92981 (17)	0.1775 (3)	0.16739 (17)	0.0392 (6)
H15A	0.9321	0.1992	0.1058	0.059*
H15B	0.9759	0.2371	0.2169	0.059*
H15C	0.8535	0.1825	0.1611	0.059*
C16	1.08067 (14)	0.0566 (2)	0.37816 (13)	0.0189 (4)
H16A	1.0633	0.0604	0.4353	0.023*
H16B	1.0961	0.1438	0.3634	0.023*
C17	1.18452 (15)	−0.0267 (2)	0.40117 (15)	0.0256 (5)
H17A	1.2461	0.0075	0.4575	0.038*
H17B	1.2042	−0.0268	0.3460	0.038*
H17C	1.1689	−0.1134	0.4146	0.038*

	U11	U22	U33	U12	U13	U23
Br1	0.02492 (10)	0.03337 (14)	0.02163 (10)	0.00625 (9)	0.00871 (7)	0.00300 (9)
Co1	0.01015 (13)	0.01029 (18)	0.00981 (15)	−0.00021 (13)	0.00367 (11)	−0.00054 (14)
O1	0.0486 (9)	0.0161 (8)	0.0359 (8)	−0.0111 (7)	0.0320 (7)	−0.0081 (7)
O2	0.0167 (5)	0.0160 (7)	0.0148 (6)	−0.0032 (5)	0.0084 (5)	−0.0023 (6)
O3	0.0195 (6)	0.0154 (7)	0.0119 (6)	−0.0016 (5)	0.0027 (5)	0.0017 (5)
O4	0.0166 (5)	0.0111 (7)	0.0152 (6)	0.0006 (5)	0.0069 (5)	0.0005 (6)
N1	0.0139 (6)	0.0131 (8)	0.0122 (7)	0.0000 (6)	0.0049 (5)	−0.0001 (6)
N2	0.0163 (6)	0.0176 (9)	0.0131 (7)	−0.0036 (6)	0.0040 (5)	0.0003 (7)
C1	0.0163 (7)	0.0141 (10)	0.0157 (8)	0.0017 (7)	0.0076 (6)	0.0007 (8)
C2	0.0208 (8)	0.0127 (10)	0.0178 (9)	−0.0038 (8)	0.0119 (7)	−0.0002 (8)
C3	0.0222 (8)	0.0189 (10)	0.0177 (9)	−0.0027 (8)	0.0109 (7)	−0.0003 (8)
C4	0.0302 (9)	0.0212 (11)	0.0310 (11)	0.0018 (9)	0.0209 (8)	−0.0018 (10)
C5	0.0403 (11)	0.0244 (12)	0.0278 (11)	−0.0071 (10)	0.0240 (9)	−0.0107 (10)
C6	0.0286 (9)	0.0330 (13)	0.0193 (9)	−0.0096 (9)	0.0116 (8)	−0.0070 (10)
C7	0.0191 (8)	0.0245 (12)	0.0218 (9)	−0.0035 (8)	0.0089 (7)	−0.0021 (9)
C8	0.0167 (7)	0.0112 (9)	0.0133 (8)	0.0005 (7)	0.0059 (6)	−0.0002 (7)
C9	0.0138 (7)	0.0132 (9)	0.0110 (8)	−0.0004 (7)	0.0044 (6)	0.0006 (8)
C10	0.0155 (7)	0.0143 (10)	0.0149 (8)	0.0044 (7)	0.0051 (6)	0.0042 (8)
C11	0.0199 (8)	0.0108 (9)	0.0169 (9)	−0.0002 (7)	0.0060 (7)	−0.0006 (8)
C12	0.0137 (7)	0.0160 (10)	0.0150 (8)	−0.0015 (7)	0.0037 (6)	−0.0023 (8)
C13	0.0133 (7)	0.0100 (9)	0.0135 (8)	0.0024 (7)	0.0026 (6)	−0.0004 (7)
C14	0.0255 (9)	0.0390 (14)	0.0146 (9)	−0.0125 (10)	0.0071 (7)	0.0024 (10)
C15	0.0280 (10)	0.0483 (16)	0.0315 (12)	−0.0094 (11)	0.0023 (9)	0.0222 (12)
C16	0.0179 (8)	0.0189 (11)	0.0161 (9)	−0.0066 (8)	0.0033 (7)	−0.0018 (8)
C17	0.0181 (8)	0.0306 (12)	0.0242 (10)	−0.0013 (9)	0.0049 (7)	0.0041 (9)

Br1—C3	1.9053 (18)	C6—C7	1.388 (3)
Co1—O2	2.0559 (12)	C6—H6	0.9300
Co1—O2i	2.0559 (12)	C7—H7	0.9300
Co1—O4i	2.1272 (13)	C8—H8	0.9300
Co1—N1i	2.1783 (14)	C9—C8	1.384 (2)
O1—C1	1.242 (2)	C9—C10	1.393 (3)
O2—C1	1.264 (2)	C9—C13	1.503 (2)
O3—C13	1.244 (2)	C10—C11	1.388 (2)
O4—Co1	2.1272 (13)	C10—H10	0.9300
O4—H41	0.82 (3)	C11—H11	0.9300
O4—H42	0.78 (3)	C12—C11	1.385 (2)
N1—C12	1.340 (2)	C12—H12	0.9300
N1—C8	1.345 (2)	C14—C15	1.516 (3)
N1—Co1	2.1783 (14)	C14—H14A	0.9700
N2—C13	1.334 (2)	C14—H14B	0.9700
N2—C14	1.470 (2)	C15—H15A	0.9600
N2—C16	1.474 (2)	C15—H15B	0.9600
C2—C1	1.510 (2)	C15—H15C	0.9600
C2—C7	1.395 (2)	C16—C17	1.518 (3)
C3—C2	1.384 (3)	C16—H16A	0.9700
C3—C4	1.395 (3)	C16—H16B	0.9700
C4—C5	1.381 (3)	C17—H17A	0.9600
C4—H4	0.9300	C17—H17B	0.9600
C5—H5	0.9300	C17—H17C	0.9600
C6—C5	1.386 (3)
O2—Co1—O2i	180.00 (5)	C6—C7—C2	120.88 (18)
O2—Co1—O4	87.71 (5)	C6—C7—H7	119.6
O2i—Co1—O4	92.29 (5)	N1—C8—C9	123.11 (17)
O2—Co1—O4i	92.29 (5)	N1—C8—H8	118.4
O2i—Co1—O4i	87.71 (5)	C9—C8—H8	118.4
O2—Co1—N1	90.60 (5)	C8—C9—C10	119.13 (15)
O2i—Co1—N1	89.40 (5)	C8—C9—C13	122.05 (16)
O2—Co1—N1i	89.40 (5)	C10—C9—C13	118.68 (15)
O2i—Co1—N1i	90.60 (5)	C9—C10—H10	121.1
O4i—Co1—O4	180.00 (7)	C11—C10—C9	117.90 (16)
O4—Co1—N1	87.18 (5)	C11—C10—H10	121.1
O4i—Co1—N1	92.82 (5)	C10—C11—H11	120.4
O4—Co1—N1i	92.82 (5)	C12—C11—C10	119.25 (18)
O4i—Co1—N1i	87.18 (5)	C12—C11—H11	120.4
N1i—Co1—N1	180.00 (13)	N1—C12—C11	123.24 (16)
C1—O2—Co1	128.18 (12)	N1—C12—H12	118.4
Co1—O4—H41	121.8 (17)	C11—C12—H12	118.4
Co1—O4—H42	100.9 (18)	O3—C13—N2	122.44 (15)
H42—O4—H41	109 (2)	O3—C13—C9	118.27 (15)
C8—N1—Co1	119.70 (12)	N2—C13—C9	119.29 (15)
C12—N1—Co1	122.99 (11)	N2—C14—C15	112.75 (18)
C12—N1—C8	117.32 (15)	N2—C14—H14A	109.0
C13—N2—C14	125.02 (15)	N2—C14—H14B	109.0
C13—N2—C16	118.37 (15)	C15—C14—H14A	109.0
C14—N2—C16	116.09 (14)	C15—C14—H14B	109.0
O1—C1—O2	126.67 (17)	H14A—C14—H14B	107.8
O1—C1—C2	118.94 (15)	C14—C15—H15A	109.5
O2—C1—C2	114.40 (16)	C14—C15—H15B	109.5
C3—C2—C1	121.13 (16)	C14—C15—H15C	109.5
C3—C2—C7	117.86 (17)	H15A—C15—H15B	109.5
C7—C2—C1	120.95 (16)	H15A—C15—H15C	109.5
C2—C3—Br1	119.59 (14)	H15B—C15—H15C	109.5
C2—C3—C4	122.13 (17)	N2—C16—C17	111.41 (16)
C4—C3—Br1	118.26 (14)	N2—C16—H16A	109.3
C3—C4—H4	120.6	N2—C16—H16B	109.3
C5—C4—C3	118.71 (19)	C17—C16—H16A	109.3
C5—C4—H4	120.6	C17—C16—H16B	109.3
C4—C5—C6	120.46 (18)	H16A—C16—H16B	108.0
C4—C5—H5	119.8	C16—C17—H17A	109.5
C6—C5—H5	119.8	C16—C17—H17B	109.5
C5—C6—C7	119.88 (18)	C16—C17—H17C	109.5
C5—C6—H6	120.1	H17A—C17—H17B	109.5
C7—C6—H6	120.1	H17A—C17—H17C	109.5
C2—C7—H7	119.6	H17B—C17—H17C	109.5
O4—Co1—O2—C1	−175.42 (14)	C3—C2—C1—O1	−86.0 (2)
O4i—Co1—O2—C1	4.58 (14)	C3—C2—C1—O2	94.2 (2)
N1—Co1—O2—C1	−88.27 (14)	C7—C2—C1—O1	96.9 (2)
N1i—Co1—O2—C1	91.73 (14)	C7—C2—C1—O2	−82.9 (2)
Co1—O2—C1—O1	12.3 (3)	C1—C2—C7—C6	175.44 (17)
Co1—O2—C1—C2	−167.89 (11)	C3—C2—C7—C6	−1.8 (3)
C8—N1—Co1—O2	−61.76 (13)	Br1—C3—C2—C1	4.6 (2)
C8—N1—Co1—O2i	118.24 (13)	Br1—C3—C4—C5	179.62 (15)
C8—N1—Co1—O4	25.92 (13)	Br1—C3—C2—C7	−178.19 (14)
C8—N1—Co1—O4i	−154.08 (13)	C2—C3—C4—C5	−1.4 (3)
C12—N1—Co1—O2	118.37 (14)	C4—C3—C2—C1	−174.33 (17)
C12—N1—Co1—O2i	−61.63 (14)	C4—C3—C2—C7	2.9 (3)
C12—N1—Co1—O4	−153.95 (14)	C3—C4—C5—C6	−1.2 (3)
C12—N1—Co1—O4i	26.05 (14)	C7—C6—C5—C4	2.2 (3)
Co1—N1—C8—C9	179.40 (13)	C5—C6—C7—C2	−0.7 (3)
Co1—N1—C12—C11	−178.31 (13)	C10—C9—C8—N1	−1.4 (3)
C8—N1—C12—C11	1.8 (3)	C13—C9—C8—N1	−177.05 (15)
C12—N1—C8—C9	−0.7 (2)	C8—C9—C10—C11	2.4 (3)
C14—N2—C13—O3	174.95 (18)	C13—C9—C10—C11	178.18 (15)
C14—N2—C13—C9	−4.8 (3)	C8—C9—C13—O3	114.69 (19)
C16—N2—C13—O3	3.6 (3)	C8—C9—C13—N2	−65.5 (2)
C16—N2—C13—C9	−176.22 (15)	C10—C9—C13—O3	−61.0 (2)
C13—N2—C14—C15	110.3 (2)	C10—C9—C13—N2	118.79 (19)
C13—N2—C16—C17	88.6 (2)	C9—C10—C11—C12	−1.4 (3)
C16—N2—C14—C15	−78.2 (2)	N1—C12—C11—C10	−0.8 (3)
C14—N2—C16—C17	−83.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H41···O3ii	0.82 (3)	1.94 (3)	2.757 (2)	174 (3)
O4—H42···O1i	0.78 (3)	1.90 (3)	2.644 (2)	159 (2)
C4—H4···O1iii	0.93	2.56	3.184 (3)	125
C10—H10···O2iv	0.93	2.44	3.368 (2)	174
C12—H12···O3v	0.93	2.33	3.259 (2)	179
C16—H16A···O3vi	0.97	2.57	3.506 (2)	163
C16—H16B···O1ii	0.97	2.52	3.460 (3)	164

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H41⋯O3i	0.82 (3)	1.94 (3)	2.757 (2)	174 (3)
O4—H42⋯O1ii	0.78 (3)	1.90 (3)	2.644 (2)	159 (2)
C4—H4⋯O1iii	0.93	2.56	3.184 (3)	125
C10—H10⋯O2iv	0.93	2.44	3.368 (2)	174
C12—H12⋯O3v	0.93	2.33	3.259 (2)	179
C16—H16A⋯O3vi	0.97	2.57	3.506 (2)	163
C16—H16B⋯O1i	0.97	2.52	3.460 (3)	164

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