Diaqua­bis(N,N-diethyl­nicotinamide-κN1)bis­[4-(dimethyl­amino)benzoato-κO]nickel(II)

Hökelek, T.; Süzen, Y.; Tercan, B.; Aybirdi, Ö.; Necefoğlu, H.

doi:10.1107/S1600536809030098

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 8| August 2009| Pages m1015-m1016

doi:10.1107/S1600536809030098

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Diaquabis(N,N-diethylnicotinamide-κN¹)bis[4-(dimethylamino)benzoato-κO]nickel(II)

Tuncer Hökelek,^a ^* Yasemin Süzen,^b Barış Tercan,^c Özgür Aybirdi ^d and Hacali Necefoğlu ^d

^aDepartment of Physics, Hacettepe University, 06800 Beytepe, Ankara, Turkey, ^bDepartment of Chemistry, Faculty of Science, Anadolu University, 26470 Yenibağlar, Eskişehir, Turkey, ^cDepartment of Physics, Karabük University, 78050, Karabük, Turkey, and ^dDepartment of Chemistry, Kafkas University, 63100 Kars, Turkey
^*Correspondence e-mail: merzifon@hacettepe.edu.tr

(Received 28 July 2009; accepted 29 July 2009; online 31 July 2009)

The centrosymmetric title Ni^II complex, [Ni(C₉H₁₀NO₂)₂(C₁₀H₁₄N₂O)₂(H₂O)₂], contains two dimethylaminobenzoate (DMAB), two diethylnicotinamide (DENA) ligands and two water molecules, all of them monodentate. The four O atoms in the equatorial plane around the Ni^II atom form a slightly distorted square-planar arrangement, while the slightly distorted octahedral coordination is completed by the two pyridine N atoms of the DENA ligands in axial positions. The Ni^II atom is displaced by 0.681 (1) Å out of the least-squares plane of the carboxylate group. The dihedral angle between the carboxylate group and the adjacent benzene ring is 5.61 (7)°, while the pyridine and benzene rings are oriented at a dihedral angle of 73.20 (4)°. An intramolecular O—H⋯O hydrogen bond results in the formation of a six-membered ring with a twisted conformation. In the crystal structure, intermolecular O—H⋯O and C—H⋯O hydrogen bonds link molecules into a three-dimensional network. Two weak C—H⋯π interactions are also present.

Related literature

For our ongoing investigations of the transition metal complexes of nicotinamide, and/or the nicotinic acid derivative N,N-diethylnicotinamide, an important respiratory stimulant, see: Bigoli et al. (1972 ); Krishnamachari (1974 ). For related structures, see: Hökelek et al. (2009 ); Sertçelik et al. (2009 ).

Experimental

Crystal data

[Ni(C₉H₁₀NO₂)₂(C₁₀H₁₄N₂O)₂(H₂O)₂]
M_r = 779.57
Monoclinic, P 2₁ /c
a = 6.5081 (1) Å
b = 20.3157 (3) Å
c = 14.7235 (2) Å
β = 98.487 (2)°
V = 1925.37 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.56 mm⁻¹
T = 100 K
0.53 × 0.43 × 0.28 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.751, T_max = 0.851
18748 measured reflections
4819 independent reflections
4332 reflections with I > 2σ(I)
R_int = 0.019

Refinement

R[F² > 2σ(F²)] = 0.029
wR(F²) = 0.076
S = 1.04
4819 reflections
253 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.41 e Å⁻³

Table 1
Selected bond lengths (Å)

Ni1—O1	2.0498 (8)
Ni1—O4	2.0842 (9)
Ni1—N1	2.0962 (10)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H41⋯O2ⁱ	0.84 (2)	1.97 (2)	2.7875 (12)	163 (2)
O4—H42⋯O2	0.85 (2)	1.82 (2)	2.6552 (12)	165.9 (18)
C11—H11⋯O3ⁱⁱ	0.93	2.45	3.3641 (15)	167
C18—H18A⋯O3ⁱⁱⁱ	0.96	2.48	3.4038 (17)	161
C19—H19B⋯Cg1^iv	0.96	2.82	3.7203 (15)	157
C15—H15A⋯Cg2^v	0.96	2.91	3.7575 (16)	148
Symmetry codes: (i) -x, -y+1, -z+1; (ii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) x, y, z+1; (iv) -x+1, -y, -z+1; (v) x-1, y, z. Cg1 and Cg2 are the centroids of the C2–C7 and N1/C8–C12 rings, respectively.

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 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809030098/xu2570sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809030098/xu2570Isup2.hkl

checkCIF report

Comment top

As a part of our ongoing investigation on transition metal complexes of nicotinamide (NA), one form of niacin (Krishnamachari, 1974), and/or the nicotinic acid derivative N,N-diethylnicotinamide (DENA), an important respiratory stimulant (Bigoli et al., 1972), the title compound was synthesized and its crystal structure is reported herein.

The title compound is a monomeric complex, with Ni^II ion on a centre of symmetry, consisting of two DENA and two dimethylaminobenzoate (DMAB) ligands and two water molecules. The structures of similar comlexes of Ni^II ion, [Ni(C₈H₅O₃)₂(C₁₀H₁₄N₂O)₂(H₂O)₂] (Sertçelik et al., 2009) and [Ni(C₇H₄ClO₂)₂(C₁₀H₁₄N₂O)₂(H₂O)₂] (Hökelek et al., 2009) have also been determined.

In the title compound, all ligands are monodentate. The four O atoms (O1, O4, and the symmetry-related atoms, O1', O4') in the equatorial plane around the Ni atom form a slightly distorted square-planar arrangement, while the slightly distorted octahedral coordination is completed by the two pyridine N atoms (N1, N1') of the DENA ligands at 2.0962 (10) Å from the Ni atom in the axial positions (Fig. 1 and Table 1). The average Ni—O bond length is 2.0670 (9) Å and the Ni atom is displaced out of the least-squares plane of the carboxylate group (O1/C1/O2) by -0.681 (1) Å. The dihedral angle between the planar carboxylate group and the benzene ring A (C2—C7) is 5.61 (7)°, while that between rings A and B (N1/C8—C12) is 73.20 (4)°. Intramolecular O—H···O hydrogen bond results in the formation of a six-membered ring C (Ni1/O1/O2/O4/C1/H42) having twisted conformation.

In the crystal structure, intermolecular O—H···O and C—H···O hydrogen bonds (Table 2) link the molecules into a three-dimensional network, in which they may be effective in the stabilization of the structure. Two weak C—H···π interactions (Table 1) are also found.

Related literature top

For our ongoing investigation of the transition metal complexes of nicotinamide (NA), one form of niacin), and/or the nicotinic acid derivative N,N-diethylnicotinamide, an important respiratory stimulant, see: Bigoli et al. (1972); Krishnamachari (1974). For related structures, see: Hökelek et al. (2009); Sertçelik et al. (2009). Cg1 and Cg2 are the centroids of the C2–C7 and N1/C8–C12 rings, respectively.

Experimental top

The title compound was prepared by the reaction of NiSO₄.6H₂O (1.31 g, 5 mmol) in H₂O (50 ml) and DENA (1.78 g, 10 mmol) in H₂O (50 ml) with sodium p-dimethylaminobenzoate (1.88 g, 10 mmol) in H₂O (100 ml). The mixture was filtered and set aside to crystallize at ambient temperature for one week, 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) and PLATON (Spek, 2009).

Figures top

Fig. 1. The molecular structure of the title molecule with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. Primed atoms are generated by the symmetry operator:(') -x, -y, -z. Dashed lines indicate intramolecular hydrogen bonding.

Diaquabis(N,N-diethylnicotinamide-κN¹)bis[4- (dimethylamino)benzoato-κO]nickel(II) top

Crystal data top

[Ni(C₉H₁₀NO₂)₂(C₁₀H₁₄N₂O)₂(H₂O)₂]	F(000) = 828
M_r = 779.57	D_x = 1.345 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9995 reflections
a = 6.5081 (1) Å	θ = 2.4–28.4°
b = 20.3157 (3) Å	µ = 0.56 mm⁻¹
c = 14.7235 (2) Å	T = 100 K
β = 98.487 (2)°	Block, blue
V = 1925.37 (5) Å³	0.53 × 0.43 × 0.28 mm
Z = 2

Data collection top

Bruker Kappa APEXII CCD area-detector diffractometer	4819 independent reflections
Radiation source: fine-focus sealed tube	4332 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.019
ϕ and ω scans	θ_max = 28.4°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −8→8
T_min = 0.751, T_max = 0.851	k = −25→27
18748 measured reflections	l = −19→19

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.076	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0382P)² + 0.8491P] where P = (F_o² + 2F_c²)/3
4819 reflections	(Δ/σ)_max = 0.001
253 parameters	Δρ_max = 0.47 e Å⁻³
0 restraints	Δρ_min = −0.41 e Å⁻³

Crystal data top

[Ni(C₉H₁₀NO₂)₂(C₁₀H₁₄N₂O)₂(H₂O)₂]	V = 1925.37 (5) Å³
M_r = 779.57	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 6.5081 (1) Å	µ = 0.56 mm⁻¹
b = 20.3157 (3) Å	T = 100 K
c = 14.7235 (2) Å	0.53 × 0.43 × 0.28 mm
β = 98.487 (2)°

Data collection top

Bruker Kappa APEXII CCD area-detector diffractometer	4819 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	4332 reflections with I > 2σ(I)
T_min = 0.751, T_max = 0.851	R_int = 0.019
18748 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	0 restraints
wR(F²) = 0.076	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.47 e Å⁻³
4819 reflections	Δρ_min = −0.41 e Å⁻³
253 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	0.5000	0.5000	0.5000	0.01159 (6)
O1	0.46213 (13)	0.50364 (4)	0.63567 (6)	0.01499 (17)
O2	0.12365 (13)	0.52742 (4)	0.62891 (5)	0.01770 (17)
O3	0.24871 (14)	0.28574 (5)	0.24645 (6)	0.02031 (19)
O4	0.21205 (14)	0.54434 (4)	0.46008 (6)	0.01635 (17)
H41	0.122 (3)	0.5242 (11)	0.4234 (13)	0.039 (5)*
H42	0.169 (3)	0.5441 (9)	0.5121 (14)	0.039 (5)*
N1	0.37272 (15)	0.40504 (5)	0.48904 (6)	0.01379 (19)
N2	−0.07839 (16)	0.27925 (5)	0.28157 (7)	0.0179 (2)
N3	0.31666 (19)	0.39407 (6)	1.02652 (7)	0.0242 (2)
C1	0.29426 (19)	0.50566 (5)	0.66964 (7)	0.0135 (2)
C2	0.30181 (18)	0.47867 (6)	0.76460 (7)	0.0145 (2)
C3	0.12187 (19)	0.47318 (6)	0.80487 (8)	0.0177 (2)
H3	−0.0035	0.4882	0.7731	0.021*
C4	0.1257 (2)	0.44578 (6)	0.89121 (8)	0.0197 (2)
H4	0.0029	0.4423	0.9161	0.024*
C5	0.3124 (2)	0.42317 (6)	0.94177 (8)	0.0182 (2)
C6	0.4949 (2)	0.43026 (7)	0.90178 (8)	0.0204 (2)
H6	0.6216	0.4170	0.9342	0.024*
C7	0.48766 (19)	0.45671 (6)	0.81467 (8)	0.0177 (2)
H7	0.6096	0.4599	0.7890	0.021*
C8	0.28565 (18)	0.38146 (6)	0.40728 (7)	0.0142 (2)
H8	0.2801	0.4084	0.3559	0.017*
C9	0.20358 (18)	0.31856 (6)	0.39614 (7)	0.0141 (2)
C10	0.21297 (19)	0.27802 (6)	0.47281 (8)	0.0174 (2)
H10	0.1598	0.2355	0.4673	0.021*
C11	0.30290 (19)	0.30200 (6)	0.55766 (8)	0.0176 (2)
H11	0.3104	0.2760	0.6100	0.021*
C12	0.38123 (18)	0.36540 (6)	0.56268 (7)	0.0158 (2)
H12	0.4425	0.3813	0.6195	0.019*
C13	0.12500 (19)	0.29353 (6)	0.30122 (8)	0.0149 (2)
C14	−0.2321 (2)	0.29609 (7)	0.34147 (9)	0.0241 (3)
H14A	−0.3490	0.3180	0.3053	0.029*
H14B	−0.1700	0.3268	0.3880	0.029*
C15	−0.3107 (2)	0.23647 (9)	0.38829 (12)	0.0381 (4)
H15A	−0.3958	0.2508	0.4325	0.057*
H15B	−0.1947	0.2119	0.4188	0.057*
H15C	−0.3912	0.2091	0.3432	0.057*
C16	−0.1508 (2)	0.24500 (7)	0.19478 (9)	0.0234 (3)
H16A	−0.0881	0.2653	0.1459	0.028*
H16B	−0.3002	0.2500	0.1800	0.028*
C17	−0.0974 (2)	0.17227 (7)	0.19917 (10)	0.0292 (3)
H17A	−0.1409	0.1525	0.1402	0.044*
H17B	−0.1673	0.1513	0.2444	0.044*
H17C	0.0500	0.1670	0.2157	0.044*
C18	0.1327 (3)	0.39476 (7)	1.07082 (9)	0.0301 (3)
H18A	0.1616	0.3730	1.1292	0.045*
H18B	0.0219	0.3723	1.0328	0.045*
H18C	0.0924	0.4395	1.0799	0.045*
C19	0.5140 (2)	0.37889 (7)	1.08181 (9)	0.0273 (3)
H19A	0.4902	0.3617	1.1401	0.041*
H19B	0.5962	0.4182	1.0913	0.041*
H19C	0.5863	0.3468	1.0507	0.041*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.01140 (11)	0.01277 (11)	0.01029 (10)	−0.00191 (7)	0.00061 (7)	0.00090 (7)
O1	0.0140 (4)	0.0182 (4)	0.0128 (4)	−0.0029 (3)	0.0018 (3)	0.0004 (3)
O2	0.0151 (4)	0.0226 (4)	0.0150 (4)	0.0013 (3)	0.0009 (3)	0.0008 (3)
O3	0.0219 (5)	0.0234 (5)	0.0160 (4)	−0.0044 (4)	0.0040 (3)	−0.0023 (3)
O4	0.0145 (4)	0.0197 (4)	0.0143 (4)	−0.0009 (3)	0.0006 (3)	0.0025 (3)
N1	0.0130 (5)	0.0144 (5)	0.0139 (4)	−0.0008 (4)	0.0018 (3)	0.0009 (3)
N2	0.0162 (5)	0.0170 (5)	0.0192 (5)	−0.0022 (4)	−0.0016 (4)	−0.0012 (4)
N3	0.0285 (6)	0.0277 (6)	0.0172 (5)	0.0012 (5)	0.0058 (4)	0.0072 (4)
C1	0.0165 (5)	0.0112 (5)	0.0125 (5)	−0.0029 (4)	0.0012 (4)	−0.0020 (4)
C2	0.0171 (6)	0.0140 (5)	0.0125 (5)	−0.0016 (4)	0.0027 (4)	−0.0008 (4)
C3	0.0159 (6)	0.0204 (6)	0.0168 (5)	0.0008 (5)	0.0024 (4)	0.0011 (4)
C4	0.0189 (6)	0.0223 (6)	0.0194 (5)	−0.0004 (5)	0.0077 (4)	0.0022 (4)
C5	0.0245 (6)	0.0159 (5)	0.0147 (5)	−0.0004 (5)	0.0042 (4)	0.0010 (4)
C6	0.0187 (6)	0.0242 (6)	0.0177 (5)	0.0030 (5)	0.0009 (4)	0.0038 (4)
C7	0.0157 (6)	0.0208 (6)	0.0174 (5)	0.0005 (5)	0.0044 (4)	0.0021 (4)
C8	0.0134 (5)	0.0156 (5)	0.0135 (5)	−0.0004 (4)	0.0021 (4)	0.0019 (4)
C9	0.0129 (5)	0.0153 (5)	0.0142 (5)	−0.0001 (4)	0.0018 (4)	−0.0004 (4)
C10	0.0194 (6)	0.0138 (5)	0.0193 (5)	−0.0021 (4)	0.0036 (4)	0.0017 (4)
C11	0.0202 (6)	0.0174 (6)	0.0154 (5)	0.0007 (5)	0.0030 (4)	0.0041 (4)
C12	0.0160 (6)	0.0183 (6)	0.0129 (5)	0.0009 (4)	0.0009 (4)	0.0010 (4)
C13	0.0179 (6)	0.0103 (5)	0.0158 (5)	−0.0018 (4)	−0.0003 (4)	0.0014 (4)
C14	0.0156 (6)	0.0278 (7)	0.0285 (6)	0.0027 (5)	0.0018 (5)	0.0014 (5)
C15	0.0214 (7)	0.0479 (10)	0.0471 (9)	0.0047 (7)	0.0118 (6)	0.0191 (7)
C16	0.0233 (7)	0.0214 (6)	0.0223 (6)	−0.0049 (5)	−0.0066 (5)	−0.0020 (5)
C17	0.0324 (8)	0.0206 (7)	0.0331 (7)	−0.0061 (6)	−0.0004 (6)	−0.0057 (5)
C18	0.0427 (9)	0.0274 (7)	0.0238 (6)	0.0071 (6)	0.0174 (6)	0.0082 (5)
C19	0.0373 (8)	0.0272 (7)	0.0166 (5)	0.0057 (6)	0.0016 (5)	0.0050 (5)

Geometric parameters (Å, º) top

Ni1—O1	2.0498 (8)	C8—H8	0.9300
Ni1—O1ⁱ	2.0498 (8)	C9—C8	1.3853 (16)
Ni1—O4	2.0842 (9)	C9—C10	1.3915 (15)
Ni1—O4ⁱ	2.0842 (9)	C9—C13	1.5042 (15)
Ni1—N1	2.0962 (10)	C10—H10	0.9300
Ni1—N1ⁱ	2.0962 (10)	C11—C10	1.3874 (16)
O1—C1	1.2675 (14)	C11—C12	1.3831 (17)
O2—C1	1.2615 (15)	C11—H11	0.9300
O3—C13	1.2309 (15)	C12—H12	0.9300
O4—H41	0.84 (2)	C14—H14A	0.9700
O4—H42	0.85 (2)	C14—H14B	0.9700
N1—C8	1.3411 (14)	C15—C14	1.519 (2)
N1—C12	1.3452 (14)	C15—H15A	0.9600
N2—C13	1.3443 (16)	C15—H15B	0.9600
N2—C14	1.4682 (16)	C15—H15C	0.9600
N3—C18	1.4457 (17)	C16—N2	1.4700 (15)
N3—C19	1.4485 (18)	C16—H16A	0.9700
C2—C1	1.4958 (15)	C16—H16B	0.9700
C2—C7	1.3937 (17)	C17—C16	1.5173 (19)
C3—C2	1.3930 (16)	C17—H17A	0.9600
C3—C4	1.3846 (16)	C17—H17B	0.9600
C3—H3	0.9300	C17—H17C	0.9600
C4—H4	0.9300	C18—H18A	0.9600
C5—N3	1.3773 (15)	C18—H18B	0.9600
C5—C4	1.4050 (18)	C18—H18C	0.9600
C5—C6	1.4086 (17)	C19—H19A	0.9600
C6—C7	1.3850 (16)	C19—H19B	0.9600
C6—H6	0.9300	C19—H19C	0.9600
C7—H7	0.9300

O1—Ni1—O1ⁱ	180.000 (1)	C8—C9—C10	118.69 (10)
O1—Ni1—O4	91.54 (3)	C8—C9—C13	119.61 (10)
O1ⁱ—Ni1—O4	88.46 (3)	C10—C9—C13	121.45 (10)
O1—Ni1—O4ⁱ	88.46 (3)	C9—C10—H10	120.5
O1ⁱ—Ni1—O4ⁱ	91.54 (3)	C11—C10—C9	118.99 (11)
O1—Ni1—N1	90.30 (3)	C11—C10—H10	120.5
O1ⁱ—Ni1—N1	89.70 (3)	C10—C11—H11	120.7
O1—Ni1—N1ⁱ	89.70 (3)	C12—C11—C10	118.58 (10)
O1ⁱ—Ni1—N1ⁱ	90.30 (3)	C12—C11—H11	120.7
O4—Ni1—O4ⁱ	180.0	N1—C12—C11	122.91 (11)
O4—Ni1—N1	92.72 (4)	N1—C12—H12	118.5
O4ⁱ—Ni1—N1	87.28 (4)	C11—C12—H12	118.5
O4—Ni1—N1ⁱ	87.28 (4)	O3—C13—N2	123.34 (11)
O4ⁱ—Ni1—N1ⁱ	92.72 (4)	O3—C13—C9	119.12 (11)
N1—Ni1—N1ⁱ	180.0	N2—C13—C9	117.51 (10)
C1—O1—Ni1	128.34 (8)	N2—C14—C15	113.05 (12)
Ni1—O4—H41	118.7 (14)	N2—C14—H14A	109.0
Ni1—O4—H42	98.5 (13)	N2—C14—H14B	109.0
H41—O4—H42	106.5 (18)	C15—C14—H14A	109.0
C8—N1—C12	118.12 (10)	C15—C14—H14B	109.0
C8—N1—Ni1	120.51 (7)	H14A—C14—H14B	107.8
C12—N1—Ni1	121.34 (8)	C14—C15—H15A	109.5
C13—N2—C14	123.83 (10)	C14—C15—H15B	109.5
C13—N2—C16	117.93 (10)	C14—C15—H15C	109.5
C14—N2—C16	118.24 (11)	H15A—C15—H15B	109.5
C5—N3—C18	119.82 (11)	H15A—C15—H15C	109.5
C5—N3—C19	119.89 (11)	H15B—C15—H15C	109.5
C18—N3—C19	118.24 (11)	N2—C16—C17	112.45 (11)
O1—C1—C2	116.46 (10)	N2—C16—H16A	109.1
O2—C1—O1	124.98 (10)	N2—C16—H16B	109.1
O2—C1—C2	118.55 (10)	C17—C16—H16A	109.1
C3—C2—C1	120.90 (11)	C17—C16—H16B	109.1
C3—C2—C7	117.88 (10)	H16A—C16—H16B	107.8
C7—C2—C1	121.20 (10)	C16—C17—H17A	109.5
C2—C3—H3	119.3	C16—C17—H17B	109.5
C4—C3—C2	121.37 (11)	C16—C17—H17C	109.5
C4—C3—H3	119.3	H17A—C17—H17B	109.5
C3—C4—C5	121.00 (11)	H17A—C17—H17C	109.5
C3—C4—H4	119.5	H17B—C17—H17C	109.5
C5—C4—H4	119.5	N3—C18—H18A	109.5
N3—C5—C4	121.38 (11)	N3—C18—H18B	109.5
N3—C5—C6	121.13 (12)	N3—C18—H18C	109.5
C4—C5—C6	117.48 (10)	H18A—C18—H18B	109.5
C5—C6—H6	119.6	H18A—C18—H18C	109.5
C7—C6—C5	120.76 (11)	H18B—C18—H18C	109.5
C7—C6—H6	119.6	N3—C19—H19A	109.5
C2—C7—H7	119.3	N3—C19—H19B	109.5
C6—C7—C2	121.48 (11)	N3—C19—H19C	109.5
C6—C7—H7	119.3	H19A—C19—H19B	109.5
N1—C8—C9	122.70 (10)	H19A—C19—H19C	109.5
N1—C8—H8	118.7	H19B—C19—H19C	109.5
C9—C8—H8	118.7

O4—Ni1—O1—C1	24.97 (9)	C7—C2—C1—O2	−177.04 (11)
O4ⁱ—Ni1—O1—C1	−155.03 (9)	C1—C2—C7—C6	−178.48 (11)
N1—Ni1—O1—C1	−67.76 (9)	C3—C2—C7—C6	−0.08 (18)
N1ⁱ—Ni1—O1—C1	112.24 (9)	C4—C3—C2—C1	177.32 (11)
O1—Ni1—N1—C8	156.38 (9)	C4—C3—C2—C7	−1.09 (18)
O1ⁱ—Ni1—N1—C8	−23.62 (9)	C2—C3—C4—C5	0.7 (2)
O4—Ni1—N1—C8	64.83 (9)	C4—C5—N3—C18	−8.82 (19)
O4ⁱ—Ni1—N1—C8	−115.17 (9)	C4—C5—N3—C19	−172.22 (12)
O1—Ni1—N1—C12	−25.63 (9)	C6—C5—N3—C18	172.36 (13)
O1ⁱ—Ni1—N1—C12	154.37 (9)	C6—C5—N3—C19	8.97 (19)
O4—Ni1—N1—C12	−117.18 (9)	N3—C5—C4—C3	−178.04 (12)
O4ⁱ—Ni1—N1—C12	62.82 (9)	C6—C5—C4—C3	0.81 (19)
Ni1—O1—C1—O2	−25.08 (16)	N3—C5—C6—C7	176.89 (12)
Ni1—O1—C1—C2	153.63 (8)	C4—C5—C6—C7	−1.96 (19)
Ni1—N1—C8—C9	178.55 (8)	C5—C6—C7—C2	1.6 (2)
C12—N1—C8—C9	0.49 (17)	C10—C9—C8—N1	−0.41 (18)
Ni1—N1—C12—C11	−178.58 (9)	C13—C9—C8—N1	−174.79 (11)
C8—N1—C12—C11	−0.54 (17)	C8—C9—C10—C11	0.36 (17)
C14—N2—C13—O3	−171.82 (11)	C13—C9—C10—C11	174.63 (11)
C14—N2—C13—C9	9.85 (17)	C8—C9—C13—O3	64.89 (15)
C16—N2—C13—O3	7.90 (18)	C8—C9—C13—N2	−116.71 (12)
C16—N2—C13—C9	−170.42 (10)	C10—C9—C13—O3	−109.33 (13)
C13—N2—C14—C15	−108.56 (14)	C10—C9—C13—N2	69.07 (15)
C16—N2—C14—C15	71.71 (15)	C12—C11—C10—C9	−0.40 (18)
C3—C2—C1—O1	−174.19 (11)	C10—C11—C12—N1	0.51 (18)
C3—C2—C1—O2	4.60 (17)	C17—C16—N2—C13	76.55 (15)
C7—C2—C1—O1	4.16 (16)	C17—C16—N2—C14	−103.71 (14)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H41···O2ⁱⁱ	0.84 (2)	1.97 (2)	2.7875 (12)	163 (2)
O4—H42···O2	0.85 (2)	1.82 (2)	2.6552 (12)	165.9 (18)
C11—H11···O3ⁱⁱⁱ	0.93	2.45	3.3641 (15)	167
C18—H18A···O3^iv	0.96	2.48	3.4038 (17)	161
C19—H19B···Cg1^v	0.96	2.82	3.7203 (15)	157
C15—H15A···Cg2^vi	0.96	2.91	3.7575 (16)	148

Symmetry codes: (ii) −x, −y+1, −z+1; (iii) x, −y+1/2, z+1/2; (iv) x, y, z+1; (v) −x+1, −y, −z+1; (vi) x−1, y, z.

Experimental details

Crystal data
Chemical formula	[Ni(C₉H₁₀NO₂)₂(C₁₀H₁₄N₂O)₂(H₂O)₂]
M_r	779.57
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	6.5081 (1), 20.3157 (3), 14.7235 (2)
β (°)	98.487 (2)
V (Å³)	1925.37 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.56
Crystal size (mm)	0.53 × 0.43 × 0.28

Data collection
Diffractometer	Bruker Kappa APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.751, 0.851
No. of measured, independent and observed [I > 2σ(I)] reflections	18748, 4819, 4332
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.076, 1.04
No. of reflections	4819
No. of parameters	253
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.47, −0.41

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Selected bond lengths (Å) top

Ni1—O1	2.0498 (8)	Ni1—N1	2.0962 (10)
Ni1—O4	2.0842 (9)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H41···O2ⁱ	0.84 (2)	1.97 (2)	2.7875 (12)	163 (2)
O4—H42···O2	0.85 (2)	1.82 (2)	2.6552 (12)	165.9 (18)
C11—H11···O3ⁱⁱ	0.93	2.45	3.3641 (15)	167
C18—H18A···O3ⁱⁱⁱ	0.96	2.48	3.4038 (17)	161
C19—H19B···Cg1^iv	0.96	2.82	3.7203 (15)	157
C15—H15A···Cg2^v	0.96	2.91	3.7575 (16)	148

Symmetry codes: (i) −x, −y+1, −z+1; (ii) x, −y+1/2, z+1/2; (iii) x, y, z+1; (iv) −x+1, −y, −z+1; (v) x−1, y, z.

Acknowledgements

The authors are indebted to Anadolu University and Medicinal Plants and Medicine Research Centre of Anadolu University, Eskişehir, Turkey, for the use of X-ray diffractometer.

References

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