Diaqua-bis(N,N-diethyl-nicotinamide-κN)bis-(4-formyl-benzoato-κO)nickel(II).

In the title centrosymmetric mononuclear Ni(II) compound, [Ni(C(8)H(5)O(3))(2)(C(10)H(14)N(2)O)(2)(H(2)O)(2)], the central Ni(II) atom is coordinated by two O atoms from two 4-formyl-benzoate (FOB) ligands, two O atoms from two water mol-ecules and two N atoms from two diethyl-nicotinamide (DENA) ligands. The coordination geometry is slightly distorted octa-hedral, with four O atoms in the equatorial plane and two N atoms in axial positions. Intra-molecular O-H⋯O hydrogen bonds are observed. In the crystal structure, mol-ecules are linked into chains along the a axis by inter-molecular O-H⋯O hydrogen bonds. The structure is further stabilized by π-π inter-actions between the pyridine rings of DENA units, with a centroid-centroid distance of 3.668 (2) Å.

Related literature

For general background, see: Antolini et al. (1982 ▶); Bigoli et al. (1972 ▶); Nadzhafov et al. (1981 ▶); Shnulin et al. (1981 ▶). For related structures, see: Hökelek et al. (1995 ▶, 1997 ▶, 2007 ▶, 2008 ▶); Hökelek & Necefouglu (1996 ▶, 1997 ▶); Hökelek & Necefoğlu (2007 ▶); Sertçelik et al. (2009 ▶).

Experimental

Crystal data

[Ni(C8H5O3)2(C10H14N2O)2(H2O)2]

M = 749.43

Triclinic,

a = 7.2909 (2) Å

b = 8.6883 (3) Å

c = 15.9037 (4) Å

α = 85.034 (5)°

β = 78.576 (4)°

γ = 67.594 (3)°

V = 912.85 (5) Å3

Z = 1

Mo Kα radiation

μ = 0.59 mm−1

T = 294 K

0.35 × 0.20 × 0.15 mm

Data collection

Rigaku R-AXIS RAPID-S diffractometer

Absorption correction: multi-scan (Blessing, 1995 ▶) T min = 0.870, T max = 0.918

19676 measured reflections

3740 independent reflections

2797 reflections with I > 2σ(I)

R int = 0.098

Refinement

R[F 2 > 2σ(F 2)] = 0.062

wR(F 2) = 0.122

S = 1.04

3740 reflections

242 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.50 e Å−3

Δρmin = −0.31 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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 Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809006345/ci2769sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809006345/ci2769Isup2.hkl

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

[Ni(C8H5O3)2(C10H14N2O)2(H2O)2]	Z = 1
Mr = 749.43	F(000) = 394
Triclinic, P1	Dx = 1.363 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.2909 (2) Å	Cell parameters from 4227 reflections
b = 8.6883 (3) Å	θ = 2.5–26.4°
c = 15.9037 (4) Å	µ = 0.59 mm−1
α = 85.034 (5)°	T = 294 K
β = 78.576 (4)°	Prism, green
γ = 67.594 (3)°	0.35 × 0.20 × 0.15 mm
V = 912.85 (5) Å3

Rigaku R-AXIS RAPID-S diffractometer	3740 independent reflections
Radiation source: fine-focus sealed tube	2797 reflections with I > 2σ(I)
graphite	Rint = 0.098
ω scans	θmax = 26.4°, θmin = 2.5°
Absorption correction: multi-scan (Blessing, 1995)	h = −9→9
Tmin = 0.870, Tmax = 0.918	k = −10→10
19676 measured reflections	l = −19→19

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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0235P)2 + 0.8051P] where P = (Fo2 + 2Fc2)/3
3740 reflections	(Δ/σ)max = 0.001
242 parameters	Δρmax = 0.50 e Å−3
3 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 > 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
O5	−0.2711 (4)	−0.0197 (4)	0.06069 (16)	0.0494 (6)
H52	−0.284 (6)	0.028 (4)	0.1070 (13)	0.069 (14)*
H51	−0.260 (6)	−0.1180 (19)	0.074 (2)	0.072 (15)*
Ni1	0.0000	0.0000	0.0000	0.03948 (19)
O1	0.0244 (3)	0.1122 (3)	0.10462 (14)	0.0465 (6)
O2	−0.2567 (4)	0.1272 (3)	0.19683 (16)	0.0569 (7)
N1	0.1775 (4)	−0.2306 (3)	0.04762 (17)	0.0427 (7)
O4	0.7320 (4)	−0.3311 (3)	0.12366 (16)	0.0579 (7)
C1	−0.0812 (5)	0.1254 (4)	0.1788 (2)	0.0430 (8)
C12	0.4355 (5)	−0.3815 (4)	0.1297 (2)	0.0423 (8)
C13	0.3191 (5)	−0.2372 (4)	0.0918 (2)	0.0433 (8)
H13	0.3401	−0.1398	0.0974	0.052*
C7	0.2092 (5)	0.1420 (4)	0.2370 (2)	0.0467 (8)
H7	0.2787	0.1384	0.1810	0.056*
C9	0.1550 (5)	−0.3738 (4)	0.0380 (2)	0.0467 (8)
H9	0.0593	−0.3722	0.0067	0.056*
C2	0.0178 (5)	0.1355 (4)	0.2521 (2)	0.0420 (8)
N2	0.6115 (5)	−0.4182 (4)	0.2506 (2)	0.0617 (9)
C3	−0.0823 (5)	0.1368 (4)	0.3360 (2)	0.0502 (9)
H3	−0.2093	0.1304	0.3472	0.060*
C11	0.4075 (5)	−0.5277 (4)	0.1196 (2)	0.0477 (9)
H11	0.4824	−0.6269	0.1445	0.057*
O3	0.4414 (5)	0.1916 (5)	0.4558 (2)	0.0974 (11)
C14	0.6023 (5)	−0.3740 (4)	0.1690 (2)	0.0474 (9)
C4	0.0071 (6)	0.1476 (5)	0.4030 (2)	0.0559 (10)
H4	−0.0606	0.1483	0.4591	0.067*
C6	0.2976 (5)	0.1538 (5)	0.3041 (2)	0.0523 (9)
H6	0.4251	0.1592	0.2932	0.063*
C10	0.2674 (5)	−0.5233 (4)	0.0723 (2)	0.0505 (9)
H10	0.2483	−0.6202	0.0635	0.061*
C5	0.1956 (6)	0.1575 (5)	0.3878 (2)	0.0533 (9)
C17	0.7912 (7)	−0.4225 (6)	0.2841 (3)	0.0746 (13)
H17A	0.8047	−0.4912	0.3356	0.090*
H17B	0.9119	−0.4723	0.2417	0.090*
C15	0.4604 (7)	−0.4666 (6)	0.3106 (3)	0.0740 (13)
H15A	0.3689	−0.4823	0.2785	0.089*
H15B	0.5285	−0.5725	0.3373	0.089*
C16	0.3433 (9)	−0.3450 (9)	0.3777 (4)	0.137 (3)
H16A	0.2414	−0.3797	0.4119	0.206*
H16B	0.2804	−0.2383	0.3518	0.206*
H16C	0.4309	−0.3367	0.4134	0.206*
C8	0.2863 (7)	0.1717 (6)	0.4606 (3)	0.0767 (13)
H8	0.2159	0.1645	0.5154	0.092*
C18	0.7725 (8)	−0.2525 (6)	0.3038 (3)	0.0961 (17)
H18A	0.8938	−0.2582	0.3212	0.144*
H18B	0.6600	−0.2068	0.3494	0.144*
H18C	0.7518	−0.1827	0.2537	0.144*

	U11	U22	U33	U12	U13	U23
O5	0.0454 (14)	0.0569 (17)	0.0485 (16)	−0.0216 (13)	−0.0106 (12)	0.0032 (14)
Ni1	0.0359 (3)	0.0445 (4)	0.0398 (4)	−0.0152 (3)	−0.0123 (3)	0.0044 (3)
O1	0.0473 (14)	0.0542 (15)	0.0420 (14)	−0.0207 (12)	−0.0141 (11)	0.0019 (11)
O2	0.0440 (14)	0.0733 (18)	0.0544 (15)	−0.0224 (13)	−0.0070 (12)	−0.0074 (13)
N1	0.0374 (15)	0.0452 (17)	0.0475 (17)	−0.0160 (13)	−0.0122 (12)	0.0030 (13)
O4	0.0500 (15)	0.0703 (18)	0.0611 (16)	−0.0315 (14)	−0.0132 (13)	0.0098 (14)
C1	0.0424 (19)	0.0387 (19)	0.046 (2)	−0.0103 (15)	−0.0139 (16)	0.0022 (15)
C12	0.0368 (18)	0.050 (2)	0.0411 (19)	−0.0174 (16)	−0.0105 (15)	0.0058 (16)
C13	0.0418 (18)	0.0436 (19)	0.047 (2)	−0.0158 (16)	−0.0144 (16)	0.0009 (16)
C7	0.048 (2)	0.053 (2)	0.0386 (19)	−0.0192 (17)	−0.0045 (15)	−0.0002 (16)
C9	0.046 (2)	0.054 (2)	0.046 (2)	−0.0236 (18)	−0.0159 (16)	0.0037 (17)
C2	0.0421 (19)	0.0426 (19)	0.0410 (19)	−0.0144 (16)	−0.0106 (15)	0.0013 (15)
N2	0.061 (2)	0.080 (2)	0.057 (2)	−0.0371 (18)	−0.0232 (16)	0.0143 (18)
C3	0.044 (2)	0.057 (2)	0.048 (2)	−0.0182 (18)	−0.0081 (16)	0.0019 (18)
C11	0.0444 (19)	0.046 (2)	0.051 (2)	−0.0137 (17)	−0.0145 (16)	0.0106 (17)
O3	0.101 (3)	0.155 (3)	0.069 (2)	−0.076 (3)	−0.0352 (19)	0.005 (2)
C14	0.044 (2)	0.050 (2)	0.050 (2)	−0.0176 (17)	−0.0140 (17)	0.0077 (17)
C4	0.062 (2)	0.066 (3)	0.038 (2)	−0.024 (2)	−0.0041 (17)	−0.0028 (18)
C6	0.051 (2)	0.061 (2)	0.051 (2)	−0.0257 (19)	−0.0137 (17)	−0.0005 (18)
C10	0.054 (2)	0.046 (2)	0.057 (2)	−0.0224 (18)	−0.0179 (18)	0.0045 (17)
C5	0.058 (2)	0.062 (2)	0.044 (2)	−0.025 (2)	−0.0139 (18)	0.0018 (18)
C17	0.081 (3)	0.078 (3)	0.076 (3)	−0.033 (3)	−0.038 (2)	0.014 (2)
C15	0.081 (3)	0.092 (3)	0.057 (3)	−0.040 (3)	−0.019 (2)	0.009 (2)
C16	0.102 (5)	0.176 (7)	0.131 (5)	−0.059 (5)	0.026 (4)	−0.069 (5)
C8	0.081 (3)	0.106 (4)	0.054 (3)	−0.042 (3)	−0.024 (2)	−0.003 (2)
C18	0.128 (5)	0.085 (4)	0.094 (4)	−0.046 (3)	−0.049 (3)	−0.002 (3)

O5—Ni1	2.084 (2)	N2—C17	1.496 (5)
O5—H52	0.85 (3)	C3—C4	1.380 (5)
O5—H51	0.84 (2)	C3—H3	0.93
Ni1—O1	2.069 (2)	C11—C10	1.371 (5)
Ni1—O1i	2.069 (2)	C11—H11	0.93
Ni1—O5i	2.084 (2)	O3—C8	1.194 (5)
Ni1—N1	2.100 (3)	C4—C5	1.382 (5)
Ni1—N1i	2.100 (3)	C4—H4	0.93
O1—C1	1.263 (4)	C6—C5	1.386 (5)
O2—C1	1.249 (4)	C6—H6	0.93
N1—C9	1.340 (4)	C10—H10	0.93
N1—C13	1.341 (4)	C5—C8	1.478 (5)
O4—C14	1.227 (4)	C17—C18	1.486 (6)
C1—C2	1.511 (4)	C17—H17A	0.97
C12—C13	1.384 (4)	C17—H17B	0.97
C12—C11	1.389 (5)	C15—C16	1.459 (6)
C12—C14	1.498 (4)	C15—H15A	0.97
C13—H13	0.93	C15—H15B	0.97
C7—C6	1.380 (4)	C16—H16A	0.96
C7—C2	1.391 (4)	C16—H16B	0.96
C7—H7	0.93	C16—H16C	0.96
C9—C10	1.379 (5)	C8—H8	0.93
C9—H9	0.93	C18—H18A	0.96
C2—C3	1.388 (5)	C18—H18B	0.96
N2—C14	1.328 (4)	C18—H18C	0.96
N2—C15	1.473 (5)
Ni1—O5—H52	98 (3)	C10—C11—C12	118.8 (3)
Ni1—O5—H51	113 (3)	C10—C11—H11	120.6
H52—O5—H51	106 (2)	C12—C11—H11	120.6
O1—Ni1—O1i	180.00 (6)	O4—C14—N2	121.3 (3)
O1—Ni1—O5	92.91 (10)	O4—C14—C12	118.6 (3)
O1i—Ni1—O5	87.09 (10)	N2—C14—C12	120.1 (3)
O1—Ni1—O5i	87.09 (10)	C3—C4—C5	121.0 (3)
O1i—Ni1—O5i	92.91 (10)	C3—C4—H4	119.5
O5—Ni1—O5i	180.00 (19)	C5—C4—H4	119.5
O1—Ni1—N1	88.53 (10)	C7—C6—C5	119.8 (3)
O1i—Ni1—N1	91.47 (10)	C7—C6—H6	120.1
O5—Ni1—N1	93.76 (10)	C5—C6—H6	120.1
O5i—Ni1—N1	86.24 (10)	C11—C10—C9	119.3 (3)
O1—Ni1—N1i	91.47 (10)	C11—C10—H10	120.3
O1i—Ni1—N1i	88.53 (10)	C9—C10—H10	120.3
O5—Ni1—N1i	86.24 (10)	C4—C5—C6	119.4 (3)
O5i—Ni1—N1i	93.76 (10)	C4—C5—C8	119.8 (4)
N1—Ni1—N1i	180.0 (2)	C6—C5—C8	120.8 (4)
C1—O1—Ni1	126.8 (2)	C18—C17—N2	111.3 (4)
C9—N1—C13	117.2 (3)	C18—C17—H17A	109.4
C9—N1—Ni1	123.6 (2)	N2—C17—H17A	109.4
C13—N1—Ni1	119.3 (2)	C18—C17—H17B	109.4
O2—C1—O1	125.9 (3)	N2—C17—H17B	109.4
O2—C1—C2	117.7 (3)	H17A—C17—H17B	108.0
O1—C1—C2	116.3 (3)	C16—C15—N2	113.6 (4)
C13—C12—C11	118.2 (3)	C16—C15—H15A	108.8
C13—C12—C14	117.4 (3)	N2—C15—H15A	108.8
C11—C12—C14	123.8 (3)	C16—C15—H15B	108.8
N1—C13—C12	123.4 (3)	N2—C15—H15B	108.8
N1—C13—H13	118.3	H15A—C15—H15B	107.7
C12—C13—H13	118.3	C15—C16—H16A	109.5
C6—C7—C2	120.9 (3)	C15—C16—H16B	109.5
C6—C7—H7	119.6	H16A—C16—H16B	109.5
C2—C7—H7	119.6	C15—C16—H16C	109.5
N1—C9—C10	123.0 (3)	H16A—C16—H16C	109.5
N1—C9—H9	118.5	H16B—C16—H16C	109.5
C10—C9—H9	118.5	O3—C8—C5	126.2 (4)
C3—C2—C7	119.0 (3)	O3—C8—H8	116.9
C3—C2—C1	119.8 (3)	C5—C8—H8	116.9
C7—C2—C1	121.2 (3)	C17—C18—H18A	109.5
C14—N2—C15	125.2 (3)	C17—C18—H18B	109.5
C14—N2—C17	117.6 (3)	H18A—C18—H18B	109.5
C15—N2—C17	117.1 (3)	C17—C18—H18C	109.5
C4—C3—C2	119.9 (3)	H18A—C18—H18C	109.5
C4—C3—H3	120.1	H18B—C18—H18C	109.5
C2—C3—H3	120.1
O5—Ni1—O1—C1	10.8 (3)	C7—C2—C3—C4	1.2 (5)
O5i—Ni1—O1—C1	−169.2 (3)	C1—C2—C3—C4	−179.4 (3)
N1—Ni1—O1—C1	−82.9 (3)	C13—C12—C11—C10	0.4 (5)
N1i—Ni1—O1—C1	97.1 (3)	C14—C12—C11—C10	−171.1 (3)
O1—Ni1—N1—C9	146.8 (3)	C15—N2—C14—O4	178.1 (4)
O1i—Ni1—N1—C9	−33.2 (3)	C17—N2—C14—O4	−3.2 (6)
O5—Ni1—N1—C9	54.0 (3)	C15—N2—C14—C12	−4.0 (6)
O5i—Ni1—N1—C9	−126.0 (3)	C17—N2—C14—C12	174.7 (3)
O1—Ni1—N1—C13	−31.7 (2)	C13—C12—C14—O4	−57.3 (5)
O1i—Ni1—N1—C13	148.3 (2)	C11—C12—C14—O4	114.3 (4)
O5—Ni1—N1—C13	−124.5 (3)	C13—C12—C14—N2	124.7 (4)
O5i—Ni1—N1—C13	55.5 (3)	C11—C12—C14—N2	−63.7 (5)
Ni1—O1—C1—O2	−26.2 (5)	C2—C3—C4—C5	0.1 (6)
Ni1—O1—C1—C2	152.2 (2)	C2—C7—C6—C5	0.7 (5)
C9—N1—C13—C12	−2.3 (5)	C12—C11—C10—C9	−1.6 (5)
Ni1—N1—C13—C12	176.3 (2)	N1—C9—C10—C11	0.8 (6)
C11—C12—C13—N1	1.6 (5)	C3—C4—C5—C6	−1.0 (6)
C14—C12—C13—N1	173.7 (3)	C3—C4—C5—C8	179.0 (4)
C13—N1—C9—C10	1.1 (5)	C7—C6—C5—C4	0.7 (6)
Ni1—N1—C9—C10	−177.5 (3)	C7—C6—C5—C8	−179.4 (4)
C6—C7—C2—C3	−1.6 (5)	C14—N2—C17—C18	78.7 (5)
C6—C7—C2—C1	179.0 (3)	C15—N2—C17—C18	−102.4 (5)
O2—C1—C2—C3	3.7 (5)	C14—N2—C15—C16	−110.3 (5)
O1—C1—C2—C3	−174.9 (3)	C17—N2—C15—C16	71.0 (6)
O2—C1—C2—C7	−177.0 (3)	C4—C5—C8—O3	−175.0 (5)
O1—C1—C2—C7	4.5 (5)	C6—C5—C8—O3	5.1 (7)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H51···O4ii	0.84 (2)	1.97 (2)	2.796 (4)	170 (3)
O5—H52···O2	0.85 (3)	1.81 (3)	2.646 (4)	168 (4)

Table 1

Selected bond lengths (Å)

O5—Ni1	2.084 (2)
Ni1—O1	2.069 (2)
Ni1—N1	2.100 (3)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H51⋯O4i	0.84 (2)	1.97 (2)	2.796 (4)	170 (3)
O5—H52⋯O2	0.85 (3)	1.81 (3)	2.646 (4)	168 (4)

Symmetry code: (i) .