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

In the mononuclear title compound, [Ni(C(8)H(7)O(3))(2)(C(6)H(6)N(2)O)(2)(H(2)O)(2)]·2H(2)O, the Ni(II) ion is located on a crystallographic inversion center. The asymmetric unit further contains one 4-meth-oxy-benzoate anion, one nicotinamide (NA) ligand and one coordinated and one uncoordinated water mol-ecule; all ligands are monodentate. The four O atoms in the equatorial plane around the Ni(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 7.2 (1)°, while the pyridine and benzene rings are oriented at a dihedral angle of 72.80 (4)°. An intra-molecular 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,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

[Ni(C8H7O3)2(C6H6N2O)2(H2O)2]·2H2O

M = 677.28

Triclinic,

a = 8.1279 (2) Å

b = 9.7006 (2) Å

c = 10.0636 (3) Å

α = 101.637 (3)°

β = 91.634 (2)°

γ = 105.137 (3)°

V = 747.42 (4) Å3

Z = 1

Mo Kα radiation

μ = 0.72 mm−1

T = 100 K

0.35 × 0.26 × 0.19 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.797, T max = 0.871

13749 measured reflections

3740 independent reflections

3454 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.026

wR(F 2) = 0.067

S = 1.04

3740 reflections

228 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.41 e Å−3

Δρmin = −0.32 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 datablocks I, global. DOI: 10.1107/S1600536810025985/ci5126sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810025985/ci5126Isup2.hkl

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

[Ni(C8H7O3)2(C6H6N2O)2(H2O)2]·2H2O	Z = 1
Mr = 677.28	F(000) = 354
Triclinic, P1	Dx = 1.505 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.1279 (2) Å	Cell parameters from 7665 reflections
b = 9.7006 (2) Å	θ = 2.2–28.4°
c = 10.0636 (3) Å	µ = 0.72 mm−1
α = 101.637 (3)°	T = 100 K
β = 91.634 (2)°	Block, blue
γ = 105.137 (3)°	0.35 × 0.26 × 0.19 mm
V = 747.42 (4) Å3

Bruker Kappa APEXII CCD area-detector diffractometer	3740 independent reflections
Radiation source: fine-focus sealed tube	3454 reflections with I > 2σ(I)
graphite	Rint = 0.024
φ and ω scans	θmax = 28.4°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −10→10
Tmin = 0.797, Tmax = 0.871	k = −12→12
13749 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)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.067	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0304P)2 + 0.3607P] where P = (Fo2 + 2Fc2)/3
3740 reflections	(Δ/σ)max = 0.001
228 parameters	Δρmax = 0.41 e Å−3
0 restraints	Δρmin = −0.32 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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
Ni1	1.0000	0.5000	0.5000	0.01031 (7)
O1	0.84093 (11)	0.34709 (9)	0.34598 (9)	0.01344 (18)
O2	0.97158 (13)	0.37223 (10)	0.15603 (9)	0.0186 (2)
O3	0.51173 (13)	−0.29261 (10)	0.00777 (10)	0.0227 (2)
O4	1.23447 (12)	−0.12322 (10)	0.38559 (10)	0.01808 (19)
O5	0.84001 (12)	0.41637 (10)	0.63798 (10)	0.01381 (18)
H51	0.824 (2)	0.328 (2)	0.6383 (18)	0.026 (5)*
H52	0.880 (3)	0.466 (2)	0.710 (2)	0.033 (5)*
O6	1.09929 (14)	0.36688 (11)	−0.10135 (11)	0.0217 (2)
H61	1.060 (2)	0.3618 (18)	−0.0275 (19)	0.020*
H62	1.093 (2)	0.444 (2)	−0.1194 (17)	0.020*
N1	1.15013 (13)	0.35208 (11)	0.50331 (10)	0.0123 (2)
N2	1.00731 (15)	−0.08680 (12)	0.27740 (11)	0.0164 (2)
H21	0.955 (2)	−0.027 (2)	0.2615 (17)	0.021 (4)*
H22	0.976 (2)	−0.178 (2)	0.2312 (19)	0.028 (5)*
C1	0.86838 (16)	0.29893 (13)	0.22424 (12)	0.0132 (2)
C2	0.77440 (16)	0.14302 (13)	0.16204 (12)	0.0136 (2)
C3	0.65161 (17)	0.06356 (14)	0.23287 (13)	0.0166 (3)
H3	0.6270	0.1096	0.3197	0.020*
C4	0.56565 (17)	−0.08093 (14)	0.17828 (14)	0.0186 (3)
H4	0.4811	−0.1330	0.2268	0.022*
C5	0.60317 (17)	−0.15037 (14)	0.05176 (13)	0.0166 (3)
C6	0.72616 (18)	−0.07365 (14)	−0.01936 (13)	0.0193 (3)
H6	0.7531	−0.1207	−0.1049	0.023*
C7	0.80961 (18)	0.07279 (14)	0.03580 (13)	0.0178 (3)
H7	0.8920	0.1256	−0.0138	0.021*
C8	0.5467 (2)	−0.37024 (15)	−0.11975 (15)	0.0267 (3)
H8A	0.4740	−0.4712	−0.1386	0.040*
H8B	0.6672	−0.3705	−0.1161	0.040*
H8C	0.5229	−0.3223	−0.1922	0.040*
C9	1.30962 (17)	0.40473 (14)	0.56440 (13)	0.0165 (3)
H9	1.3474	0.5053	0.6080	0.020*
C10	1.42177 (17)	0.31926 (14)	0.56686 (14)	0.0191 (3)
H10	1.5328	0.3600	0.6130	0.023*
C11	1.36869 (17)	0.17315 (14)	0.50057 (13)	0.0156 (2)
H11	1.4428	0.1119	0.5007	0.019*
C12	1.20523 (16)	0.11758 (13)	0.43385 (12)	0.0124 (2)
C13	1.09960 (16)	0.21032 (13)	0.43965 (12)	0.0124 (2)
H13	0.9867	0.1717	0.3967	0.015*
C14	1.14890 (16)	−0.04076 (13)	0.36228 (12)	0.0132 (2)

	U11	U22	U33	U12	U13	U23
Ni1	0.01171 (11)	0.00792 (11)	0.01082 (11)	0.00341 (8)	−0.00027 (8)	0.00012 (8)
O1	0.0145 (4)	0.0117 (4)	0.0131 (4)	0.0045 (3)	−0.0005 (3)	−0.0006 (3)
O2	0.0262 (5)	0.0119 (4)	0.0144 (4)	0.0005 (4)	0.0021 (4)	0.0015 (3)
O3	0.0265 (5)	0.0112 (4)	0.0244 (5)	−0.0007 (4)	−0.0025 (4)	−0.0016 (4)
O4	0.0195 (5)	0.0117 (4)	0.0246 (5)	0.0068 (4)	0.0026 (4)	0.0039 (4)
O5	0.0164 (4)	0.0100 (4)	0.0140 (4)	0.0034 (3)	−0.0002 (3)	0.0007 (3)
O6	0.0344 (6)	0.0147 (5)	0.0164 (5)	0.0076 (4)	0.0037 (4)	0.0025 (4)
N1	0.0140 (5)	0.0108 (5)	0.0123 (5)	0.0044 (4)	0.0013 (4)	0.0018 (4)
N2	0.0217 (6)	0.0112 (5)	0.0167 (5)	0.0071 (4)	−0.0002 (4)	0.0010 (4)
C1	0.0146 (6)	0.0117 (5)	0.0137 (6)	0.0052 (4)	−0.0024 (4)	0.0017 (4)
C2	0.0151 (6)	0.0112 (5)	0.0135 (6)	0.0039 (4)	−0.0024 (5)	0.0007 (4)
C3	0.0175 (6)	0.0152 (6)	0.0157 (6)	0.0043 (5)	0.0021 (5)	0.0006 (5)
C4	0.0174 (6)	0.0152 (6)	0.0211 (6)	0.0011 (5)	0.0022 (5)	0.0033 (5)
C5	0.0173 (6)	0.0111 (6)	0.0190 (6)	0.0025 (5)	−0.0049 (5)	0.0006 (5)
C6	0.0261 (7)	0.0152 (6)	0.0136 (6)	0.0041 (5)	0.0007 (5)	−0.0018 (5)
C7	0.0223 (6)	0.0139 (6)	0.0144 (6)	0.0016 (5)	0.0019 (5)	0.0014 (5)
C8	0.0364 (8)	0.0146 (6)	0.0236 (7)	0.0044 (6)	−0.0065 (6)	−0.0038 (5)
C9	0.0165 (6)	0.0115 (6)	0.0195 (6)	0.0036 (5)	−0.0013 (5)	−0.0002 (5)
C10	0.0140 (6)	0.0169 (6)	0.0250 (7)	0.0046 (5)	−0.0031 (5)	0.0013 (5)
C11	0.0161 (6)	0.0150 (6)	0.0185 (6)	0.0085 (5)	0.0029 (5)	0.0043 (5)
C12	0.0158 (6)	0.0104 (5)	0.0120 (5)	0.0044 (4)	0.0041 (4)	0.0034 (4)
C13	0.0140 (6)	0.0116 (5)	0.0117 (5)	0.0036 (4)	0.0014 (4)	0.0028 (4)
C14	0.0169 (6)	0.0110 (5)	0.0129 (5)	0.0047 (4)	0.0061 (5)	0.0037 (4)

Ni1—O1	2.0569 (9)	C2—C7	1.3904 (18)
Ni1—O1i	2.0569 (9)	C3—C4	1.3822 (18)
Ni1—O5	2.0697 (9)	C3—H3	0.95
Ni1—O5i	2.0697 (9)	C4—C5	1.3970 (19)
Ni1—N1	2.1167 (10)	C4—H4	0.95
Ni1—N1i	2.1167 (10)	C5—C6	1.3902 (19)
O1—C1	1.2681 (15)	C6—C7	1.3941 (18)
O2—C1	1.2644 (16)	C6—H6	0.95
O3—C5	1.3607 (15)	C7—H7	0.95
O3—C8	1.4274 (18)	C8—H8A	0.98
O4—C14	1.2392 (15)	C8—H8B	0.98
O5—H51	0.83 (2)	C8—H8C	0.98
O5—H52	0.79 (2)	C9—C10	1.3858 (18)
O6—H61	0.823 (18)	C9—H9	0.95
O6—H62	0.818 (18)	C10—C11	1.3867 (18)
N1—C9	1.3421 (16)	C10—H10	0.95
N1—C13	1.3434 (15)	C11—C12	1.3913 (18)
N2—C14	1.3324 (17)	C11—H11	0.95
N2—H21	0.839 (18)	C12—C13	1.3910 (17)
N2—H22	0.877 (19)	C12—C14	1.5017 (16)
C1—C2	1.5001 (17)	C13—H13	0.95
C2—C3	1.3995 (18)
O1i—Ni1—O1	180.0	C3—C4—C5	119.95 (12)
O1—Ni1—O5	88.52 (4)	C3—C4—H4	120.0
O1i—Ni1—O5	91.48 (4)	C5—C4—H4	120.0
O1—Ni1—O5i	91.48 (4)	O3—C5—C4	115.16 (12)
O1i—Ni1—O5i	88.52 (4)	O3—C5—C6	124.95 (12)
O1—Ni1—N1	88.64 (4)	C6—C5—C4	119.89 (12)
O1i—Ni1—N1	91.36 (4)	C5—C6—C7	119.52 (12)
O1—Ni1—N1i	91.36 (4)	C5—C6—H6	120.2
O1i—Ni1—N1i	88.64 (4)	C7—C6—H6	120.2
O5—Ni1—O5i	180.000 (1)	C2—C7—C6	121.20 (12)
O5—Ni1—N1	93.21 (4)	C2—C7—H7	119.4
O5i—Ni1—N1	86.79 (4)	C6—C7—H7	119.4
O5—Ni1—N1i	86.79 (4)	O3—C8—H8A	109.5
O5i—Ni1—N1i	93.21 (4)	O3—C8—H8B	109.5
N1—Ni1—N1i	180.0	O3—C8—H8C	109.5
C1—O1—Ni1	130.22 (8)	H8A—C8—H8B	109.5
C5—O3—C8	117.74 (11)	H8A—C8—H8C	109.5
Ni1—O5—H51	117.6 (12)	H8B—C8—H8C	109.5
Ni1—O5—H52	104.9 (14)	N1—C9—C10	123.11 (12)
H51—O5—H52	111.1 (19)	N1—C9—H9	118.4
H62—O6—H61	108.0 (17)	C10—C9—H9	118.4
C9—N1—Ni1	118.24 (8)	C9—C10—C11	118.69 (12)
C9—N1—C13	117.80 (11)	C9—C10—H10	120.7
C13—N1—Ni1	123.79 (8)	C11—C10—H10	120.7
C14—N2—H21	120.0 (12)	C10—C11—C12	118.98 (11)
C14—N2—H22	119.6 (12)	C10—C11—H11	120.5
H21—N2—H22	120.1 (17)	C12—C11—H11	120.5
O1—C1—C2	116.29 (11)	C11—C12—C14	118.60 (11)
O2—C1—O1	124.22 (11)	C13—C12—C11	118.44 (11)
O2—C1—C2	119.46 (11)	C13—C12—C14	122.93 (11)
C3—C2—C1	120.07 (11)	N1—C13—C12	122.95 (11)
C7—C2—C1	121.44 (12)	N1—C13—H13	118.5
C7—C2—C3	118.47 (11)	C12—C13—H13	118.5
C2—C3—H3	119.5	O4—C14—N2	122.82 (12)
C4—C3—C2	120.95 (12)	O4—C14—C12	118.87 (11)
C4—C3—H3	119.5	N2—C14—C12	118.31 (11)
O5—Ni1—O1—C1	−160.75 (10)	C1—C2—C3—C4	−178.93 (12)
O5i—Ni1—O1—C1	19.25 (10)	C7—C2—C3—C4	−0.71 (19)
N1—Ni1—O1—C1	−67.50 (10)	C1—C2—C7—C6	177.72 (12)
N1i—Ni1—O1—C1	112.50 (10)	C3—C2—C7—C6	−0.5 (2)
O1—Ni1—N1—C9	162.56 (10)	C2—C3—C4—C5	1.2 (2)
O1i—Ni1—N1—C9	−17.44 (10)	C8—O3—C5—C4	−178.85 (12)
O1—Ni1—N1—C13	−12.62 (10)	C8—O3—C5—C6	1.3 (2)
O1i—Ni1—N1—C13	167.38 (10)	C3—C4—C5—O3	179.75 (12)
O5—Ni1—N1—C9	−109.01 (10)	C3—C4—C5—C6	−0.4 (2)
O5i—Ni1—N1—C9	70.99 (10)	O3—C5—C6—C7	179.07 (13)
O5—Ni1—N1—C13	75.81 (10)	C4—C5—C6—C7	−0.7 (2)
O5i—Ni1—N1—C13	−104.19 (10)	C5—C6—C7—C2	1.2 (2)
Ni1—O1—C1—O2	−29.75 (18)	N1—C9—C10—C11	1.5 (2)
Ni1—O1—C1—C2	148.20 (9)	C9—C10—C11—C12	0.1 (2)
Ni1—N1—C9—C10	−176.80 (10)	C10—C11—C12—C13	−1.78 (19)
C13—N1—C9—C10	−1.33 (19)	C10—C11—C12—C14	179.97 (11)
Ni1—N1—C13—C12	174.71 (9)	C11—C12—C13—N1	2.04 (18)
C9—N1—C13—C12	−0.49 (18)	C14—C12—C13—N1	−179.79 (11)
O1—C1—C2—C3	6.12 (17)	C11—C12—C14—O4	13.48 (17)
O1—C1—C2—C7	−172.05 (12)	C11—C12—C14—N2	−167.30 (12)
O2—C1—C2—C3	−175.83 (11)	C13—C12—C14—O4	−164.68 (12)
O2—C1—C2—C7	6.00 (18)	C13—C12—C14—N2	14.53 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H22···O6ii	0.88 (2)	1.96 (2)	2.8306 (16)	170 (2)
O5—H51···O4iii	0.83 (2)	1.88 (2)	2.7074 (14)	171 (2)
O5—H52···O2i	0.79 (2)	1.95 (2)	2.7040 (14)	159 (2)
O6—H61···O2	0.82 (2)	1.99 (2)	2.8136 (14)	174 (2)
O6—H62···O2iv	0.82 (2)	2.08 (2)	2.8887 (15)	169 (2)
C9—H9···O1i	0.95	2.35	2.9719 (16)	123
C10—H10···O5v	0.95	2.41	3.2973 (17)	156

Table 1

Selected bond lengths (Å)

Ni1—O1	2.0569 (9)
Ni1—O5	2.0697 (9)
Ni1—N1	2.1167 (10)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H22⋯O6i	0.88 (2)	1.96 (2)	2.8306 (16)	170 (2)
O5—H51⋯O4ii	0.83 (2)	1.88 (2)	2.7074 (14)	171 (2)
O5—H52⋯O2iii	0.79 (2)	1.95 (2)	2.7040 (14)	159 (2)
O6—H61⋯O2	0.82 (2)	1.99 (2)	2.8136 (14)	174 (2)
O6—H62⋯O2iv	0.82 (2)	2.08 (2)	2.8887 (15)	169 (2)
C9—H9⋯O1iii	0.95	2.35	2.9719 (16)	123
C10—H10⋯O5v	0.95	2.41	3.2973 (17)	156

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