Diaqua-bis(2-chloro-benzoato-κO)bis-(N,N-diethyl-nicotinamide-κN)nickel(II).

In the monomeric and centrosymmetric title Ni(II) complex, [Ni(C(7)H(4)ClO(2))(2)(C(10)H(14)N(2)O)(2)(H(2)O)(2)], the Ni(II) ion is located on an inversion center. The asymmetric unit contains one 2-chloro-benzoate ligand, one diethyl-nicotinamide (DENA) ligand and one coordinating water mol-ecule, the ligands being 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 two N atoms of the DENA ligands in axial positions. The dihedral angle between the benzene ring and the attached carboxyl-ate group is 87.36 (10)°, while the pyridine and benzene rings are oriented at an angle of 41.90 (5)°. In the crystal structure, inter-molecular O-H⋯O hydrogen bonds link the mol-ecules into a two-dimensional network parallel to (10).

Related literature

For general backgroud, 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 & Necefoğlu (1996 ▶, 1997 ▶, 2007 ▶).

Experimental

Crystal data

[Ni(C7H4ClO2)2(C10H14N2O)2(H2O)2]

M = 762.31

Monoclinic,

a = 12.7505 (2) Å

b = 10.3565 (2) Å

c = 14.9673 (3) Å

β = 114.046 (1)°

V = 1804.92 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.74 mm−1

T = 100 K

0.27 × 0.18 × 0.11 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.828, T max = 0.923

16593 measured reflections

4519 independent reflections

3781 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.084

S = 1.06

4519 reflections

233 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.08 e Å−3

Δρmin = −0.39 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 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809014226/ci2776sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809014226/ci2776Isup2.hkl

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

[Ni(C7H4ClO2)2(C10H14N2O)2(H2O)2]	F(000) = 796
Mr = 762.31	Dx = 1.403 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 7783 reflections
a = 12.7505 (2) Å	θ = 2.5–28.4°
b = 10.3565 (2) Å	µ = 0.74 mm−1
c = 14.9673 (3) Å	T = 100 K
β = 114.046 (1)°	Block, blue
V = 1804.92 (6) Å3	0.27 × 0.18 × 0.11 mm
Z = 2

Bruker Kappa APEXII CCD area-detector diffractometer	4519 independent reflections
Radiation source: fine-focus sealed tube	3781 reflections with I > 2σ(I)
graphite	Rint = 0.034
φ and ω scans	θmax = 28.4°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −17→17
Tmin = 0.828, Tmax = 0.923	k = −13→12
16593 measured reflections	l = −20→18

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.084	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0456P)2 + 0.2566P] where P = (Fo2 + 2Fc2)/3
4519 reflections	(Δ/σ)max = 0.001
233 parameters	Δρmax = 1.08 e Å−3
2 restraints	Δρmin = −0.39 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	0.0000	0.5000	0.0000	0.00853 (8)
Cl1	−0.31050 (4)	0.35043 (4)	0.08471 (3)	0.02678 (11)
O1	−0.03038 (8)	0.44605 (10)	0.11794 (7)	0.0128 (2)
O2	−0.13227 (11)	0.61462 (11)	0.13322 (9)	0.0268 (3)
O3	0.43014 (9)	0.61598 (10)	0.39621 (7)	0.0151 (2)
O4	0.11786 (9)	0.34845 (10)	0.03504 (8)	0.0123 (2)
H41	0.1299 (19)	0.338 (2)	−0.0143 (13)	0.042 (6)*
H42	0.1100 (18)	0.2746 (17)	0.0570 (15)	0.043 (6)*
N1	0.13740 (10)	0.61957 (11)	0.08958 (9)	0.0114 (2)
N2	0.48379 (11)	0.49545 (12)	0.29580 (9)	0.0152 (3)
C1	−0.09075 (13)	0.50440 (14)	0.15415 (11)	0.0135 (3)
C2	−0.11211 (13)	0.42820 (14)	0.23115 (11)	0.0148 (3)
C3	−0.03393 (14)	0.42920 (16)	0.32862 (12)	0.0202 (3)
H3	0.0299	0.4830	0.3480	0.024*
C4	−0.05013 (15)	0.35049 (17)	0.39746 (12)	0.0259 (4)
H4	0.0027	0.3517	0.4624	0.031*
C5	−0.14508 (16)	0.27062 (17)	0.36887 (13)	0.0270 (4)
H5	−0.1551	0.2169	0.4145	0.032*
C6	−0.22513 (15)	0.27003 (16)	0.27308 (13)	0.0235 (4)
H6	−0.2895	0.2170	0.2541	0.028*
C7	−0.20830 (14)	0.34949 (15)	0.20560 (11)	0.0183 (3)
C8	0.14003 (12)	0.74683 (14)	0.07426 (11)	0.0136 (3)
H8	0.0804	0.7833	0.0209	0.016*
C9	0.22780 (12)	0.82654 (14)	0.13450 (11)	0.0151 (3)
H9	0.2255	0.9148	0.1223	0.018*
C10	0.31847 (12)	0.77378 (14)	0.21268 (11)	0.0139 (3)
H10	0.3776	0.8255	0.2547	0.017*
C11	0.31889 (12)	0.64090 (14)	0.22689 (10)	0.0119 (3)
C12	0.22679 (12)	0.56819 (14)	0.16507 (10)	0.0124 (3)
H12	0.2267	0.4799	0.1762	0.015*
C13	0.41594 (12)	0.58190 (13)	0.31243 (11)	0.0120 (3)
C14	0.47757 (15)	0.45998 (18)	0.19868 (12)	0.0254 (4)
H14A	0.5535	0.4670	0.1989	0.031*
H14B	0.4278	0.5205	0.1507	0.031*
C15	0.43258 (16)	0.32361 (19)	0.16849 (14)	0.0368 (5)
H15A	0.4372	0.3023	0.1078	0.055*
H15B	0.3541	0.3187	0.1605	0.055*
H15C	0.4781	0.2638	0.2181	0.055*
C16	0.58189 (13)	0.44280 (15)	0.38015 (11)	0.0166 (3)
H16A	0.5967	0.3551	0.3657	0.020*
H16B	0.5628	0.4401	0.4366	0.020*
C17	0.68933 (14)	0.52372 (17)	0.40425 (13)	0.0233 (4)
H17A	0.7512	0.4876	0.4600	0.035*
H17B	0.6750	0.6105	0.4188	0.035*
H17C	0.7098	0.5242	0.3492	0.035*

	U11	U22	U33	U12	U13	U23
Ni1	0.00850 (13)	0.00775 (13)	0.00768 (13)	0.00027 (9)	0.00159 (10)	0.00033 (9)
Cl1	0.0248 (2)	0.0307 (2)	0.0230 (2)	−0.00606 (17)	0.00789 (18)	−0.00259 (17)
O1	0.0143 (5)	0.0135 (5)	0.0110 (5)	0.0022 (4)	0.0055 (4)	0.0018 (4)
O2	0.0457 (8)	0.0154 (6)	0.0323 (7)	0.0119 (5)	0.0293 (6)	0.0083 (5)
O3	0.0180 (5)	0.0122 (5)	0.0103 (5)	0.0014 (4)	0.0008 (4)	−0.0013 (4)
O4	0.0136 (5)	0.0093 (5)	0.0121 (5)	0.0011 (4)	0.0034 (4)	0.0006 (4)
N1	0.0114 (6)	0.0109 (6)	0.0102 (6)	−0.0004 (5)	0.0027 (5)	0.0001 (5)
N2	0.0143 (6)	0.0175 (7)	0.0098 (6)	0.0038 (5)	0.0009 (5)	0.0004 (5)
C1	0.0158 (7)	0.0125 (7)	0.0126 (7)	−0.0021 (6)	0.0061 (6)	−0.0011 (6)
C2	0.0181 (7)	0.0132 (7)	0.0166 (7)	0.0037 (6)	0.0106 (6)	0.0016 (6)
C3	0.0185 (8)	0.0232 (9)	0.0194 (8)	0.0028 (6)	0.0081 (7)	0.0026 (7)
C4	0.0288 (9)	0.0322 (10)	0.0175 (8)	0.0105 (8)	0.0104 (7)	0.0082 (7)
C5	0.0380 (10)	0.0253 (9)	0.0269 (9)	0.0072 (8)	0.0228 (9)	0.0114 (7)
C6	0.0293 (9)	0.0199 (9)	0.0286 (9)	−0.0026 (7)	0.0193 (8)	0.0018 (7)
C7	0.0212 (8)	0.0181 (8)	0.0175 (8)	0.0008 (6)	0.0098 (7)	0.0002 (6)
C8	0.0125 (7)	0.0120 (7)	0.0131 (7)	0.0019 (6)	0.0018 (6)	0.0028 (6)
C9	0.0169 (7)	0.0093 (7)	0.0164 (7)	−0.0002 (6)	0.0039 (6)	0.0010 (6)
C10	0.0137 (7)	0.0125 (7)	0.0133 (7)	−0.0022 (6)	0.0033 (6)	−0.0019 (6)
C11	0.0117 (7)	0.0120 (7)	0.0097 (7)	0.0005 (5)	0.0022 (6)	−0.0006 (5)
C12	0.0144 (7)	0.0097 (7)	0.0113 (7)	0.0006 (5)	0.0032 (6)	0.0012 (5)
C13	0.0114 (7)	0.0089 (7)	0.0118 (7)	−0.0023 (5)	0.0009 (6)	−0.0005 (5)
C14	0.0223 (9)	0.0383 (10)	0.0129 (8)	0.0119 (7)	0.0042 (7)	−0.0016 (7)
C15	0.0259 (10)	0.0442 (12)	0.0291 (10)	0.0087 (8)	−0.0003 (8)	−0.0213 (9)
C16	0.0159 (7)	0.0144 (8)	0.0147 (7)	0.0054 (6)	0.0012 (6)	0.0021 (6)
C17	0.0169 (8)	0.0271 (9)	0.0214 (9)	0.0006 (7)	0.0033 (7)	−0.0046 (7)

Ni1—O1i	2.0336 (10)	C7—C2	1.390 (2)
Ni1—O1	2.0336 (10)	C7—C6	1.386 (2)
Ni1—O4	2.0867 (10)	C8—C9	1.387 (2)
Ni1—O4i	2.0867 (10)	C8—H8	0.93
Ni1—N1i	2.1181 (12)	C9—H9	0.93
Ni1—N1	2.1181 (12)	C10—C9	1.379 (2)
Cl1—C7	1.7466 (17)	C10—H10	0.93
O1—C1	1.2616 (17)	C11—C10	1.392 (2)
O2—C1	1.2435 (18)	C11—C12	1.384 (2)
O3—C13	1.2429 (17)	C12—H12	0.93
O4—H41	0.820 (15)	C13—N2	1.3369 (18)
O4—H42	0.854 (15)	C13—C11	1.501 (2)
N1—C8	1.3405 (19)	C14—H14A	0.97
N1—C12	1.3452 (18)	C14—H14B	0.97
N2—C14	1.470 (2)	C15—C14	1.522 (3)
N2—C16	1.4728 (19)	C15—H15A	0.96
C2—C3	1.392 (2)	C15—H15B	0.96
C2—C1	1.510 (2)	C15—H15C	0.96
C3—C4	1.394 (2)	C16—H16A	0.97
C3—H3	0.93	C16—H16B	0.97
C4—H4	0.93	C17—C16	1.519 (2)
C5—C4	1.382 (3)	C17—H17A	0.96
C5—H5	0.93	C17—H17B	0.96
C6—C5	1.380 (2)	C17—H17C	0.96
C6—H6	0.93
O1i—Ni1—O1	180.0	C6—C7—C2	121.94 (15)
O1i—Ni1—O4	93.00 (4)	C6—C7—Cl1	119.13 (13)
O1—Ni1—O4	87.00 (4)	N1—C8—C9	122.93 (14)
O1i—Ni1—O4i	87.00 (4)	N1—C8—H8	118.5
O1—Ni1—O4i	93.00 (4)	C9—C8—H8	118.5
O1i—Ni1—N1i	90.70 (4)	C8—C9—H9	120.3
O1—Ni1—N1i	89.30 (4)	C10—C9—C8	119.41 (14)
O1i—Ni1—N1	89.30 (4)	C10—C9—H9	120.3
O1—Ni1—N1	90.70 (4)	C9—C10—C11	118.10 (13)
O4—Ni1—O4i	180.0	C9—C10—H10	121.0
O4—Ni1—N1i	92.55 (4)	C11—C10—H10	121.0
O4i—Ni1—N1i	87.45 (4)	C10—C11—C13	118.90 (13)
O4—Ni1—N1	87.45 (4)	C12—C11—C10	119.09 (13)
O4i—Ni1—N1	92.55 (4)	C12—C11—C13	121.91 (13)
N1i—Ni1—N1	180.00 (7)	N1—C12—C11	122.94 (13)
C1—O1—Ni1	127.35 (9)	N1—C12—H12	118.5
Ni1—O4—H41	104.4 (15)	C11—C12—H12	118.5
Ni1—O4—H42	125.8 (15)	O3—C13—N2	122.60 (13)
H41—O4—H42	109 (2)	O3—C13—C11	118.39 (13)
C8—N1—Ni1	122.58 (10)	N2—C13—C11	119.01 (13)
C8—N1—C12	117.45 (12)	N2—C14—C15	112.80 (15)
C12—N1—Ni1	119.97 (9)	N2—C14—H14A	109.0
C13—N2—C14	124.98 (13)	N2—C14—H14B	109.0
C13—N2—C16	118.44 (12)	C15—C14—H14A	109.0
C14—N2—C16	116.10 (12)	C15—C14—H14B	109.0
O1—C1—C2	114.14 (12)	H14A—C14—H14B	107.8
O2—C1—O1	127.09 (14)	C14—C15—H15A	109.5
O2—C1—C2	118.77 (13)	C14—C15—H15B	109.5
C3—C2—C1	121.41 (14)	C14—C15—H15C	109.5
C7—C2—C1	120.65 (14)	H15A—C15—H15B	109.5
C7—C2—C3	117.87 (14)	H15A—C15—H15C	109.5
C2—C3—C4	120.80 (16)	H15B—C15—H15C	109.5
C2—C3—H3	119.6	N2—C16—C17	111.60 (13)
C4—C3—H3	119.6	N2—C16—H16A	109.3
C3—C4—H4	120.1	N2—C16—H16B	109.3
C5—C4—C3	119.74 (16)	C17—C16—H16A	109.3
C5—C4—H4	120.1	C17—C16—H16B	109.3
C6—C5—C4	120.52 (15)	H16A—C16—H16B	108.0
C6—C5—H5	119.7	C16—C17—H17A	109.5
C4—C5—H5	119.7	C16—C17—H17B	109.5
C5—C6—C7	119.08 (16)	C16—C17—H17C	109.5
C5—C6—H6	120.5	H17A—C17—H17B	109.5
C7—C6—H6	120.5	H17A—C17—H17C	109.5
C2—C7—Cl1	118.94 (12)	H17B—C17—H17C	109.5
O4—Ni1—O1—C1	172.55 (12)	C1—C2—C3—C4	−174.81 (14)
O4i—Ni1—O1—C1	−7.45 (12)	C7—C2—C3—C4	2.0 (2)
N1i—Ni1—O1—C1	−94.85 (12)	C2—C3—C4—C5	−0.2 (2)
N1—Ni1—O1—C1	85.15 (12)	C6—C5—C4—C3	−1.3 (3)
O1i—Ni1—N1—C8	58.61 (11)	C7—C6—C5—C4	0.8 (3)
O1—Ni1—N1—C8	−121.39 (11)	Cl1—C7—C2—C1	−5.36 (19)
O1i—Ni1—N1—C12	−121.15 (11)	Cl1—C7—C2—C3	177.78 (12)
O1—Ni1—N1—C12	58.85 (11)	C6—C7—C2—C1	174.35 (14)
O4—Ni1—N1—C8	151.65 (11)	C6—C7—C2—C3	−2.5 (2)
O4i—Ni1—N1—C8	−28.35 (11)	Cl1—C7—C6—C5	−179.16 (12)
O4—Ni1—N1—C12	−28.11 (11)	C2—C7—C6—C5	1.1 (2)
O4i—Ni1—N1—C12	151.89 (11)	N1—C8—C9—C10	1.6 (2)
Ni1—O1—C1—O2	−9.8 (2)	C11—C10—C9—C8	1.1 (2)
Ni1—O1—C1—C2	170.38 (9)	C12—C11—C10—C9	−2.7 (2)
Ni1—N1—C8—C9	177.78 (11)	C13—C11—C10—C9	−179.11 (13)
C12—N1—C8—C9	−2.5 (2)	C10—C11—C12—N1	1.8 (2)
Ni1—N1—C12—C11	−179.49 (11)	C13—C11—C12—N1	178.16 (13)
C8—N1—C12—C11	0.7 (2)	O3—C13—N2—C14	−174.33 (15)
C13—N2—C14—C15	−110.16 (17)	O3—C13—N2—C16	−2.5 (2)
C16—N2—C14—C15	77.88 (18)	C11—C13—N2—C14	5.4 (2)
C13—N2—C16—C17	−90.03 (17)	C11—C13—N2—C16	177.22 (12)
C14—N2—C16—C17	82.48 (17)	O3—C13—C11—C10	61.59 (19)
C3—C2—C1—O1	85.51 (18)	O3—C13—C11—C12	−114.75 (16)
C3—C2—C1—O2	−94.30 (19)	N2—C13—C11—C10	−118.19 (15)
C7—C2—C1—O1	−91.23 (17)	N2—C13—C11—C12	65.48 (19)
C7—C2—C1—O2	88.96 (19)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H41···O2i	0.82 (2)	1.86 (2)	2.6267 (17)	155 (2)
O4—H42···O3ii	0.85 (2)	1.93 (2)	2.7826 (15)	172 (2)

Table 1

Selected bond lengths (Å)

Ni1—O1	2.0336 (10)
Ni1—O4	2.0867 (10)
Ni1—N1	2.1181 (12)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H41⋯O2i	0.82 (2)	1.86 (2)	2.6267 (17)	155 (2)
O4—H42⋯O3ii	0.85 (2)	1.93 (2)	2.7826 (15)	172 (2)

Symmetry codes: (i) ; (ii) .