Diaqua­bis(2-chloro­benzoato-κO)bis­(N,N-diethyl­nicotinamide-κN1)nickel(II)

Hökelek, T.; Dal, H.; Tercan, B.; Özbek, F.E.; Necefoğlu, H.

doi:10.1107/S1600536809014226

Diaquabis(2-chlorobenzoato-κO)bis(N,N-diethylnicotinamide-κN¹)nickel(II)

T. Hökelek, H. Dal, B. Tercan, F. E. Özbek and H. Necefoğlu

In the monomeric and centrosymmetric title Ni^II complex, [Ni(C₇H₄ClO₂)₂(C₁₀H₁₄N₂O)₂(H₂O)₂], the Ni^II ion is located on an inversion center. The asymmetric unit contains one 2-chlorobenzoate ligand, one diethylnicotinamide (DENA) ligand and one coordinating water molecule, 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 octahedral coordination is completed by two N atoms of the DENA ligands in axial positions. The dihedral angle between the benzene ring and the attached carboxylate group is 87.36 (10)°, while the pyridine and benzene rings are oriented at an angle of 41.90 (5)°. In the crystal structure, intermolecular O—H

O hydrogen bonds link the molecules into a two-dimensional network parallel to (10 $\overline{1}$ ).

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536809014226/ci2776sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536809014226/ci2776Isup2.hkl Contains datablock I

CCDC reference: 731162

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Key indicators

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
R factor = 0.031
wR factor = 0.084
Data-to-parameter ratio = 19.4

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Alert level C
            Value of measurement temperature given =   100.000
            Value of melting point given =     0.000
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.78
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.12 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.67 Ratio

Alert level G
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          2

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

Transition metal complexes with biochemically active ligands frequently show interesting physical and/or chemical properties, as a result they may find applications in biological systems (Antolini et al., 1982). The structural functions and coordination relationships of the arylcarboxylate ion in transition metal complexes of benzoic acid derivatives change depending on the nature and position of the substituent groups on the benzene ring, the nature of the additional ligand molecule or solvent, and the medium of the synthesis (Nadzhafov et al., 1981; Shnulin et al., 1981). The nicotinic acid derivative N,N-diethylnicotinamide (DENA) is an important respiratory stimulant (Bigoli et al., 1972).

The structure determination of the title compound, (I), a nickel complex with two 2-chlorobenzoate (CB), two diethylnicotinamide (DENA) ligands and two water molecules, was undertaken in order to determine the properties of the ligands and also to compare the results obtained with those reported previously.

Compound (I) is a monomeric complex, with the Ni^II ion on a centre of symmetry. It contains two CB, two DENA ligands and two water molecules (Fig. 1). All ligands are monodentate. The four O atoms (O1, O4, and the symmetry-related atoms O1', O4') in the equatorial plane around the Ni^II ion form a slightly distorted square-planar arrangement, while the slightly distorted octahedral coordination is completed by the two N atoms of the DENA ligands (N1, N1') in the axial positions (Table 1 and Fig. 1).

The near equality of the C1—O1 [1.2616 (17) Å] and C1—O2 [1.2435 (18) Å] bonds in the carboxylate group indicates a delocalized bonding arrangement, rather than localized single and double bonds, and may be compared with the corresponding distances: 1.256 (6) and 1.245 (6) Å in [Mn(DENA)₂(C₇H₄ClO₂)₂(H₂O)₂], (II) (Hökelek et al., 2008), 1.265 (6) and 1.275 (6) Å in [Mn(C₉H₁₀NO₂)₂(H₂O)₄].2(H₂O), (III) (Hökelek & Necefoğlu, 2007), 1.260 (4) and 1.252 (4) Å in [Zn(DENA)₂(C₇H₄FO₂)₂(H₂O)₂],(IV) (Hökelek et al., 2007), 1.259 (9) and 1.273 (9) Å in Cu₂(DENA)₂(C₆H₅COO)₄, (V) (Hökelek et al., 1995), 1.279 (4) and 1.246 (4) Å in [Zn₂(DENA)₂(C₇H₅O₃)₄].2H₂O, (VI) (Hökelek & Necefoğlu, 1996), 1.251 (6) and 1.254 (7) Å in [Co(DENA)₂(C₇H₅O₃)₂(H₂O)₂], (VII) (Hökelek & Necefoğlu, 1997) and 1.278 (3) and 1.246 (3) Å in [Cu(DENA)₂(C₇H₄NO₄)₂(H₂O)₂], (VIII) (Hökelek et al., 1997). In (I), the average Ni—O bond length is 2.0602 (10) Å and the Ni1 atom is displaced out of the least-squares plane of the carboxylate group (O1/C1/O2) by -0.276 (1) Å. The dihedral angle between the planar carboxylate group and the benzene ring A (C2—C7) is 87.36 (10)°, while that between rings A and B (N1/C8—C12) is 41.90 (5)°.

In the crystal structure, intermolecular O—H···O hydrogen bonds (Table 2) link the molecules into a two-dimesional network parallel to the (1 0 1).

Related literature top

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 top

The title compound was prepared by the reaction of Ni(SO₄).6(H₂O) (1.31 g, 5 mmol) in H₂O (20 ml) and DENA (1.78 g, 10 mmol) in H₂O (20 ml) with sodium 2-chlorobenzoate (1.785 g, 10 mmol) in H₂O (50 ml). The mixture was filtered and set aside to crystallize at ambient temperature for 3 d, giving blue single crystals.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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).

Figures top

Fig. 1. The molecular structure of the title compound with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. Primed atoms are generated by the symmetry operator (- x, 1 -y, -z).

Diaquabis(2-chlorobenzoato-κO)bis(N,N- diethylnicotinamide-κN¹)nickel(II) top

Crystal data top

[Ni(C₇H₄ClO₂)₂(C₁₀H₁₄N₂O)₂(H₂O)₂]	F(000) = 796
M_r = 762.31	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0456P)² + 0.2566P] where P = (F_o² + 2F_c²)/3
4519 reflections	(Δ/σ)_max = 0.001
233 parameters	Δρ_max = 1.08 e Å⁻³
2 restraints	Δρ_min = −0.39 e Å⁻³

Crystal data top

[Ni(C₇H₄ClO₂)₂(C₁₀H₁₄N₂O)₂(H₂O)₂]	V = 1804.92 (6) Å³
M_r = 762.31	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 12.7505 (2) Å	µ = 0.74 mm⁻¹
b = 10.3565 (2) Å	T = 100 K
c = 14.9673 (3) Å	0.27 × 0.18 × 0.11 mm
β = 114.046 (1)°

Data collection top

Bruker Kappa APEXII CCD area-detector diffractometer	4519 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	3781 reflections with I > 2σ(I)
T_min = 0.828, T_max = 0.923	R_int = 0.034
16593 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	2 restraints
wR(F²) = 0.084	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 1.08 e Å⁻³
4519 reflections	Δρ_min = −0.39 e Å⁻³
233 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Symmetry code: (i) −x, −y+1, −z.

Hydrogen-bond geometry (Å, º) top

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) −x, −y+1, −z; (ii) −x+1/2, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	[Ni(C₇H₄ClO₂)₂(C₁₀H₁₄N₂O)₂(H₂O)₂]
M_r	762.31
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	12.7505 (2), 10.3565 (2), 14.9673 (3)
β (°)	114.046 (1)
V (Å³)	1804.92 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.74
Crystal size (mm)	0.27 × 0.18 × 0.11

Data collection
Diffractometer	Bruker Kappa APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.828, 0.923
No. of measured, independent and observed [I > 2σ(I)] reflections	16593, 4519, 3781
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.669

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.084, 1.06
No. of reflections	4519
No. of parameters	233
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	1.08, −0.39

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Selected bond lengths (Å) top

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