Diaqua-bis-(4-meth-oxy-benzoato-κO)bis-(nicotinamide-κN)cobalt(II) dihydrate.

In the mononuclear title compound, [Co(C(8)H(7)O(3))(2)(C(6)H(6)N(2)O)(2)(H(2)O)(2)]·2H(2)O, the Co(II) ion is located on a crystallographic inversion center. The asymmetric unit is completed by one 4-meth-oxy-benzoate anion, one nicotinamide (NA) ligand and one coordinated and one uncoordinated water mol-ecule. All ligands act in a monodentate mode. The four O atoms in the equatorial plane around the Co(II) ion 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 attached benzene ring is 6.47 (7)°, while the pyridine and benzene rings are oriented at a dihedral angle of 72.80 (4)°. An O-H⋯O hydrogen bond links the uncoordinated water mol-ecule to one of the carboxyl-ate groups. In the crystal structure, inter-molecular O-H⋯O, N-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 class="Chemical">N,N-diethyl­nicotinamide, see: Bigoli et al. (1972 ▶). For related structures, see: Hökelek et al. (1996 ▶, 2009a ▶,b ▶,c ▶); Hökelek & Necefoğlu (1998 ▶); Necefoğlu et al. (2010 ▶).

Experimental

Crystal data

[Co(C8H7O3)2(C6H6N2O)2(n class="Chemical">H2O)2]·2H2O

M = 677.52

Triclinic,

a = 8.1568 (2) Å

b = 9.7502 (2) Å

c = 10.0700 (3) Å

α = 101.151 (3)°

β = 91.796 (2)°

γ = 106.043 (3)°

V = 752.09 (4) Å3

Z = 1

Mo Kα radiation

μ = 0.64 mm−1

T = 100 K

0.45 × 0.29 × 0.24 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.799, T max = 0.856

13470 measured reflections

3776 independent reflections

3541 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.027

wR(F 2) = 0.074

S = 1.07

3776 reflections

230 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.55 e Å−3

Δρmin = −0.31 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 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810026462/cv2740sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810026462/cv2740Isup2.hkl

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

[Co(C8H7O3)2(C6H6N2O)2(H2O)2]·2H2O	Z = 1
Mr = 677.52	F(000) = 353
Triclinic, P1	Dx = 1.496 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.1568 (2) Å	Cell parameters from 9220 reflections
b = 9.7502 (2) Å	θ = 2.6–28.4°
c = 10.0700 (3) Å	µ = 0.64 mm−1
α = 101.151 (3)°	T = 100 K
β = 91.796 (2)°	Block, pink
γ = 106.043 (3)°	0.45 × 0.29 × 0.24 mm
V = 752.09 (4) Å3

Bruker Kappa APEXII CCD area-detector diffractometer	3776 independent reflections
Radiation source: fine-focus sealed tube	3541 reflections with I > 2σ(I)
graphite	Rint = 0.023
φ and ω scans	θmax = 28.5°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −10→10
Tmin = 0.799, Tmax = 0.856	k = −13→10
13470 measured reflections	l = −13→13

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)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.074	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0387P)2 + 0.2836P] where P = (Fo2 + 2Fc2)/3
3776 reflections	(Δ/σ)max < 0.001
230 parameters	Δρmax = 0.55 e Å−3
0 restraints	Δρmin = −0.31 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	0.01140 (7)
O1	0.16134 (11)	0.15267 (9)	0.15761 (8)	0.01516 (17)
O2	0.02618 (12)	0.12855 (9)	0.34523 (9)	0.02010 (19)
O3	0.49079 (13)	0.79361 (10)	0.49240 (10)	0.0241 (2)
O4	−0.23377 (11)	0.62299 (9)	0.11798 (9)	0.01950 (19)
O5	0.16105 (11)	0.08580 (10)	−0.14044 (9)	0.01498 (17)
H51	0.180 (2)	0.174 (2)	−0.145 (2)	0.038 (5)*
H52	0.118 (2)	0.034 (2)	−0.214 (2)	0.034 (5)*
O6	0.10074 (14)	−0.13088 (11)	0.39872 (10)	0.0230 (2)
H61	0.091 (3)	−0.056 (3)	0.380 (2)	0.046 (6)*
H62	0.060 (3)	−0.137 (2)	0.474 (2)	0.044 (6)*
N1	−0.15075 (13)	0.15172 (11)	−0.00112 (10)	0.01377 (19)
N2	−0.00471 (14)	0.58909 (12)	0.22425 (11)	0.0175 (2)
H21	0.028 (2)	0.680 (2)	0.2689 (18)	0.029 (4)*
H22	0.050 (2)	0.530 (2)	0.2387 (17)	0.024 (4)*
C1	0.13157 (15)	0.20178 (12)	0.27783 (11)	0.0141 (2)
C2	0.22590 (15)	0.35792 (12)	0.33911 (12)	0.0141 (2)
C3	0.35076 (16)	0.43797 (14)	0.26923 (12)	0.0181 (2)
H3	0.3764	0.3923	0.1834	0.022*
C4	0.43723 (16)	0.58247 (14)	0.32337 (13)	0.0203 (3)
H4	0.5229	0.6350	0.2755	0.024*
C5	0.39860 (16)	0.65132 (13)	0.44861 (13)	0.0177 (2)
C6	0.27348 (17)	0.57414 (14)	0.51879 (13)	0.0204 (3)
H6	0.2457	0.6207	0.6034	0.024*
C7	0.18914 (17)	0.42784 (14)	0.46397 (12)	0.0187 (2)
H7	0.1050	0.3748	0.5127	0.022*
C8	0.4554 (2)	0.87023 (15)	0.61895 (14)	0.0281 (3)
H8A	0.5296	0.9710	0.6381	0.042*
H8B	0.4770	0.8219	0.6917	0.042*
H8C	0.3352	0.8703	0.6139	0.042*
C9	−0.30977 (16)	0.09903 (13)	−0.06401 (13)	0.0179 (2)
H9	−0.3478	−0.0009	−0.1087	0.021*
C10	−0.42123 (16)	0.18327 (14)	−0.06690 (14)	0.0210 (3)
H10	−0.5321	0.1423	−0.1140	0.025*
C11	−0.36763 (16)	0.32850 (13)	0.00028 (13)	0.0173 (2)
H11	−0.4412	0.3888	−0.0002	0.021*
C12	−0.20437 (15)	0.38459 (12)	0.06844 (11)	0.0134 (2)
C13	−0.10001 (15)	0.29263 (12)	0.06338 (11)	0.0132 (2)
H13	0.0126	0.3314	0.1077	0.016*
C14	−0.14729 (15)	0.54226 (13)	0.14024 (12)	0.0143 (2)

	U11	U22	U33	U12	U13	U23
Co1	0.01336 (11)	0.00782 (11)	0.01164 (11)	0.00330 (8)	−0.00119 (8)	−0.00122 (8)
O1	0.0164 (4)	0.0127 (4)	0.0143 (4)	0.0046 (3)	−0.0009 (3)	−0.0024 (3)
O2	0.0282 (5)	0.0123 (4)	0.0153 (4)	0.0002 (4)	0.0015 (3)	0.0004 (3)
O3	0.0276 (5)	0.0107 (4)	0.0266 (5)	−0.0011 (4)	−0.0033 (4)	−0.0028 (4)
O4	0.0210 (4)	0.0117 (4)	0.0268 (5)	0.0070 (3)	0.0020 (4)	0.0029 (3)
O5	0.0177 (4)	0.0099 (4)	0.0155 (4)	0.0030 (3)	−0.0010 (3)	−0.0002 (3)
O6	0.0356 (5)	0.0144 (5)	0.0177 (5)	0.0072 (4)	0.0029 (4)	0.0006 (4)
N1	0.0159 (5)	0.0109 (5)	0.0136 (4)	0.0043 (4)	−0.0002 (4)	0.0003 (4)
N2	0.0234 (5)	0.0114 (5)	0.0171 (5)	0.0067 (4)	−0.0006 (4)	−0.0006 (4)
C1	0.0166 (5)	0.0115 (5)	0.0135 (5)	0.0055 (4)	−0.0037 (4)	0.0000 (4)
C2	0.0169 (5)	0.0110 (5)	0.0134 (5)	0.0044 (4)	−0.0020 (4)	−0.0001 (4)
C3	0.0197 (6)	0.0153 (6)	0.0171 (5)	0.0041 (5)	0.0020 (4)	−0.0007 (4)
C4	0.0195 (6)	0.0162 (6)	0.0222 (6)	0.0016 (5)	0.0025 (5)	0.0023 (5)
C5	0.0192 (6)	0.0104 (5)	0.0198 (6)	0.0018 (4)	−0.0056 (4)	−0.0011 (4)
C6	0.0277 (6)	0.0140 (6)	0.0151 (5)	0.0034 (5)	0.0000 (5)	−0.0033 (4)
C7	0.0245 (6)	0.0133 (6)	0.0144 (5)	0.0014 (5)	0.0019 (4)	0.0000 (4)
C8	0.0387 (8)	0.0135 (6)	0.0246 (7)	0.0033 (6)	−0.0079 (6)	−0.0060 (5)
C9	0.0178 (6)	0.0115 (5)	0.0215 (6)	0.0038 (4)	−0.0030 (5)	−0.0017 (4)
C10	0.0164 (6)	0.0165 (6)	0.0279 (7)	0.0055 (5)	−0.0045 (5)	−0.0003 (5)
C11	0.0173 (5)	0.0152 (6)	0.0210 (6)	0.0080 (5)	0.0017 (4)	0.0031 (5)
C12	0.0168 (5)	0.0112 (5)	0.0125 (5)	0.0045 (4)	0.0031 (4)	0.0024 (4)
C13	0.0152 (5)	0.0111 (5)	0.0123 (5)	0.0033 (4)	0.0002 (4)	0.0008 (4)
C14	0.0185 (5)	0.0114 (5)	0.0134 (5)	0.0048 (4)	0.0053 (4)	0.0024 (4)

Co1—O1	2.0831 (8)	C2—C7	1.3931 (16)
Co1—O1i	2.0831 (8)	C3—C4	1.3817 (17)
Co1—O5	2.0958 (9)	C3—H3	0.9500
Co1—O5i	2.0958 (9)	C4—C5	1.3982 (17)
Co1—N1	2.1706 (10)	C4—H4	0.9500
Co1—N1i	2.1706 (10)	C5—C6	1.3907 (18)
O1—C1	1.2698 (14)	C6—C7	1.3935 (17)
O2—C1	1.2626 (15)	C6—H6	0.9500
O3—C5	1.3603 (15)	C7—H7	0.9500
O3—C8	1.4281 (17)	C8—H8A	0.9800
O4—C14	1.2381 (15)	C8—H8B	0.9800
O5—H51	0.84 (2)	C8—H8C	0.9800
O5—H52	0.81 (2)	C9—C10	1.3865 (17)
O6—H61	0.81 (2)	C9—H9	0.9500
O6—H62	0.84 (2)	C10—C11	1.3866 (17)
N1—C9	1.3423 (15)	C10—H10	0.9500
N1—C13	1.3433 (15)	C11—C12	1.3923 (17)
N2—C14	1.3312 (16)	C11—H11	0.9500
N2—H21	0.875 (19)	C12—C13	1.3921 (16)
N2—H22	0.854 (18)	C12—C14	1.5021 (16)
C1—C2	1.5000 (16)	C13—H13	0.9500
C2—C3	1.3999 (17)
O1i—Co1—O1	180.00 (6)	C3—C4—C5	120.01 (11)
O1—Co1—O5	89.63 (3)	C3—C4—H4	120.0
O1i—Co1—O5	90.37 (3)	C5—C4—H4	120.0
O1—Co1—O5i	90.37 (3)	O3—C5—C4	115.24 (11)
O5—Co1—O5i	180.00 (5)	O3—C5—C6	124.82 (11)
O1i—Co1—O5i	89.63 (3)	C6—C5—C4	119.95 (11)
O1—Co1—N1	88.17 (3)	C5—C6—C7	119.43 (11)
O1i—Co1—N1	91.83 (3)	C5—C6—H6	120.3
O1—Co1—N1i	91.83 (3)	C7—C6—H6	120.3
O1i—Co1—N1i	88.17 (3)	C2—C7—C6	121.26 (11)
O5—Co1—N1	93.31 (4)	C2—C7—H7	119.4
O5i—Co1—N1	86.69 (4)	C6—C7—H7	119.4
O5—Co1—N1i	86.69 (4)	O3—C8—H8A	109.5
O5i—Co1—N1i	93.31 (4)	O3—C8—H8B	109.5
N1i—Co1—N1	180.00 (4)	O3—C8—H8C	109.5
C1—O1—Co1	130.19 (8)	H8A—C8—H8B	109.5
C5—O3—C8	117.77 (11)	H8A—C8—H8C	109.5
Co1—O5—H51	120.1 (13)	H8B—C8—H8C	109.5
Co1—O5—H52	104.5 (13)	N1—C9—C10	123.21 (11)
H52—O5—H51	109.5 (19)	N1—C9—H9	118.4
H62—O6—H61	107 (2)	C10—C9—H9	118.4
C9—N1—Co1	117.67 (8)	C9—C10—C11	118.68 (11)
C9—N1—C13	117.60 (10)	C9—C10—H10	120.7
C13—N1—Co1	124.61 (8)	C11—C10—H10	120.7
C14—N2—H21	119.2 (12)	C10—C11—C12	119.02 (11)
C14—N2—H22	120.4 (12)	C10—C11—H11	120.5
H22—N2—H21	120.2 (16)	C12—C11—H11	120.5
O1—C1—C2	116.55 (10)	C11—C12—C14	118.57 (10)
O2—C1—O1	124.00 (11)	C13—C12—C11	118.26 (11)
O2—C1—C2	119.43 (10)	C13—C12—C14	123.14 (11)
C3—C2—C1	120.15 (10)	N1—C13—C12	123.19 (11)
C7—C2—C1	121.38 (11)	N1—C13—H13	118.4
C7—C2—C3	118.45 (11)	C12—C13—H13	118.4
C2—C3—H3	119.6	O4—C14—N2	122.96 (11)
C4—C3—C2	120.90 (11)	O4—C14—C12	118.73 (11)
C4—C3—H3	119.6	N2—C14—C12	118.31 (10)
O5—Co1—O1—C1	158.01 (10)	O2—C1—C2—C3	176.09 (11)
O5i—Co1—O1—C1	−21.99 (10)	O2—C1—C2—C7	−5.62 (17)
N1—Co1—O1—C1	64.69 (10)	C1—C2—C3—C4	179.13 (11)
N1i—Co1—O1—C1	−115.31 (10)	C7—C2—C3—C4	0.78 (18)
O1—Co1—N1—C9	−163.03 (9)	C1—C2—C7—C6	−178.10 (11)
O1i—Co1—N1—C9	16.97 (9)	C3—C2—C7—C6	0.22 (19)
O1—Co1—N1—C13	12.88 (9)	C2—C3—C4—C5	−0.99 (19)
O1i—Co1—N1—C13	−167.12 (9)	C3—C4—C5—O3	−179.82 (11)
O5—Co1—N1—C9	107.45 (9)	C3—C4—C5—C6	0.19 (19)
O5i—Co1—N1—C9	−72.55 (9)	O3—C5—C6—C7	−179.20 (12)
O5—Co1—N1—C13	−76.64 (9)	C4—C5—C6—C7	0.79 (19)
O5i—Co1—N1—C13	103.36 (9)	C5—C6—C7—C2	−1.0 (2)
Co1—O1—C1—O2	31.88 (16)	N1—C9—C10—C11	−1.2 (2)
Co1—O1—C1—C2	−146.38 (8)	C9—C10—C11—C12	−0.15 (19)
C8—O3—C5—C4	179.22 (11)	C10—C11—C12—C13	1.50 (17)
C8—O3—C5—C6	−0.80 (19)	C10—C11—C12—C14	179.68 (11)
Co1—N1—C9—C10	177.21 (10)	C11—C12—C13—N1	−1.72 (17)
C13—N1—C9—C10	1.01 (18)	C14—C12—C13—N1	−179.81 (10)
Co1—N1—C13—C12	−175.45 (8)	C11—C12—C14—O4	−12.03 (16)
C9—N1—C13—C12	0.47 (17)	C11—C12—C14—N2	168.54 (11)
O1—C1—C2—C3	−5.57 (16)	C13—C12—C14—O4	166.05 (11)
O1—C1—C2—C7	172.73 (11)	C13—C12—C14—N2	−13.38 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H21···O6ii	0.876 (19)	1.969 (19)	2.8343 (15)	169.6 (17)
O5—H51···O4iii	0.841 (19)	1.868 (19)	2.6976 (13)	168.6 (19)
O5—H52···O2iv	0.817 (19)	1.924 (19)	2.7064 (13)	159.8 (19)
O6—H61···O2	0.81 (3)	2.10 (3)	2.9009 (14)	170 (2)
O6—H62···O2v	0.84 (2)	1.97 (2)	2.8068 (14)	173.9 (19)
C4—H4···O4vi	0.95	2.59	3.4225 (16)	146
C9—H9···O1iv	0.95	2.40	3.0325 (16)	124
C10—H10···O5vii	0.95	2.40	3.2925 (17)	156

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H21⋯O6i	0.876 (19)	1.969 (19)	2.8343 (15)	169.6 (17)
O5—H51⋯O4ii	0.841 (19)	1.868 (19)	2.6976 (13)	168.6 (19)
O5—H52⋯O2iii	0.817 (19)	1.924 (19)	2.7064 (13)	159.8 (19)
O6—H61⋯O2	0.81 (3)	2.10 (3)	2.9009 (14)	170 (2)
O6—H62⋯O2iv	0.84 (2)	1.97 (2)	2.8068 (14)	173.9 (19)
C4—H4⋯O4v	0.95	2.59	3.4225 (16)	146
C9—H9⋯O1iii	0.95	2.40	3.0325 (16)	124
C10—H10⋯O5vi	0.95	2.40	3.2925 (17)	156

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