Bis{1-[3-(diethyl-ammonio)-propyl-imino-meth-yl]naphthalen-2-olato}nickel(II) dinitrate.

The asymmetric unit of the title compound, [Ni(C(18)H(24)N(2)O)(2)](NO(3))(2), consists of one half of the centrosymmetric nickel(II) complex cation and a nitrate anion. The Ni(II) atom, lying on an inversion center, is four-coordinated by the phenolate O atoms and imine N atoms of two Schiff base ligands, forming a square-planar geometry. The O- and N-donor atoms are mutually trans. In the crystal structure, the nitrate anions are linked to the complex cations by inter-molecular N-H⋯O hydrogen bonds.

Related literature

For background to complexes with Schiff bases, see: Hamaker et al. (2010 ▶); Wang et al. (2010 ▶); Mirkhani et al. (2010 ▶); Liu & Yang (2009 ▶); Keypour et al. (2009 ▶); Adhikary et al. (2009 ▶); Peng et al. (2009 ▶). For similar nickel complexes, see: Bhatia et al. (1983 ▶); Kamenar et al. (1990 ▶); Connor et al. (2003 ▶); Lacroix et al. (2004 ▶).

Experimental

Crystal data

[Ni(C18H24N2O)2](NO3)2

M = 751.51

Monoclinic,

a = 11.096 (2) Å

b = 12.773 (3) Å

c = 12.743 (3) Å

β = 107.66 (3)°

V = 1720.9 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.63 mm−1

T = 298 K

0.22 × 0.20 × 0.20 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.875, T max = 0.885

14203 measured reflections

3689 independent reflections

2616 reflections with I > 2σ(I)

R int = 0.055

Refinement

R[F 2 > 2σ(F 2)] = 0.069

wR(F 2) = 0.209

S = 1.05

3689 reflections

237 parameters

10 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.12 e Å−3

Δρmin = −0.56 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810025663/sj5031sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810025663/sj5031Isup2.hkl

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

[Ni(C18H24N2O)2](NO3)2	F(000) = 796
Mr = 751.51	Dx = 1.450 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1931 reflections
a = 11.096 (2) Å	θ = 2.3–24.5°
b = 12.773 (3) Å	µ = 0.63 mm−1
c = 12.743 (3) Å	T = 298 K
β = 107.66 (3)°	Block, red
V = 1720.9 (6) Å3	0.22 × 0.20 × 0.20 mm
Z = 2

Bruker APEXII CCD area-detector diffractometer	3689 independent reflections
Radiation source: fine-focus sealed tube	2616 reflections with I > 2σ(I)
graphite	Rint = 0.055
ω scans	θmax = 27.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −14→14
Tmin = 0.875, Tmax = 0.885	k = −16→16
14203 measured reflections	l = −15→15

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)] = 0.069	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.209	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.1045P)2 + 2.3396P] where P = (Fo2 + 2Fc2)/3
3689 reflections	(Δ/σ)max < 0.001
237 parameters	Δρmax = 1.12 e Å−3
10 restraints	Δρmin = −0.56 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 > 2sigma(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	0.0000	0.0000	0.0311 (3)
O1	0.9986 (3)	0.1074 (2)	0.1014 (3)	0.0408 (7)
O2	0.5354 (7)	0.2034 (9)	0.9557 (8)	0.225 (5)
O3	0.4032 (8)	0.1988 (7)	0.8277 (7)	0.192 (4)
O4	0.3971 (5)	0.2888 (5)	0.9549 (6)	0.136 (3)
N1	0.8796 (3)	−0.0671 (3)	0.0330 (3)	0.0345 (8)
N2	0.5785 (3)	0.0578 (3)	−0.2176 (4)	0.0545 (11)
N3	0.4423 (5)	0.2296 (4)	0.9150 (5)	0.0721 (14)
C1	0.9022 (4)	0.0217 (3)	0.2196 (4)	0.0352 (9)
C2	0.9667 (4)	0.1028 (3)	0.1957 (4)	0.0359 (9)
C3	0.9970 (4)	0.1886 (4)	0.2757 (4)	0.0441 (11)
H3	1.0384	0.2466	0.2589	0.053*
C4	0.9685 (4)	0.1902 (4)	0.3755 (4)	0.0473 (11)
H4	0.9901	0.2484	0.4212	0.057*
C5	0.9090 (4)	0.1069 (4)	0.4066 (4)	0.0421 (10)
C6	0.8845 (4)	0.1068 (5)	0.5149 (4)	0.0547 (13)
H6	0.9079	0.1643	0.5614	0.066*
C7	0.8303 (5)	0.0261 (5)	0.5452 (5)	0.0591 (15)
H7	0.8141	0.0244	0.6126	0.071*
C8	0.7973 (4)	−0.0588 (5)	0.4694 (4)	0.0562 (14)
H8	0.7590	−0.1169	0.4898	0.067*
C9	0.8189 (4)	−0.0615 (4)	0.3639 (4)	0.0491 (12)
H9	0.7943	−0.1197	0.3187	0.059*
C10	0.8757 (4)	0.0217 (3)	0.3293 (4)	0.0394 (10)
C11	0.8539 (4)	−0.0524 (3)	0.1298 (4)	0.0371 (10)
H11	0.7939	−0.0985	0.1407	0.045*
C12	0.8045 (4)	−0.1365 (3)	−0.0545 (4)	0.0413 (10)
H12A	0.7442	−0.1746	−0.0276	0.050*
H12B	0.8601	−0.1871	−0.0727	0.050*
C13	0.7332 (4)	−0.0759 (4)	−0.1585 (4)	0.0456 (11)
H13A	0.7917	−0.0425	−0.1911	0.055*
H13B	0.6779	−0.1220	−0.2125	0.055*
C14	0.6604 (4)	0.0017 (4)	−0.1200 (5)	0.0541 (13)
H14A	0.7168	0.0506	−0.0706	0.065*
H14B	0.6090	−0.0323	−0.0805	0.065*
C15	0.4901 (5)	−0.0100 (5)	−0.2939 (8)	0.095 (3)
H15A	0.5335	−0.0566	−0.3306	0.114*
H15B	0.4280	0.0304	−0.3491	0.114*
C16	0.4293 (7)	−0.0697 (6)	−0.2234 (11)	0.162 (5)
H16A	0.4811	−0.1288	−0.1918	0.243*
H16B	0.3476	−0.0937	−0.2673	0.243*
H16C	0.4201	−0.0252	−0.1656	0.243*
C17	0.6274 (5)	0.1202 (5)	−0.2952 (6)	0.083 (2)
H17A	0.6633	0.0743	−0.3385	0.100*
H17B	0.5594	0.1602	−0.3449	0.100*
C18	0.7222 (6)	0.1889 (6)	−0.2297 (10)	0.135 (4)
H18A	0.6979	0.2124	−0.1674	0.203*
H18B	0.7311	0.2482	−0.2731	0.203*
H18C	0.8014	0.1523	−0.2045	0.203*
H2	0.548 (6)	0.100 (4)	−0.176 (4)	0.080*

	U11	U22	U33	U12	U13	U23
Ni1	0.0217 (4)	0.0292 (4)	0.0426 (5)	−0.0016 (3)	0.0100 (3)	0.0006 (3)
O1	0.0354 (15)	0.0351 (16)	0.056 (2)	−0.0065 (12)	0.0206 (14)	−0.0047 (14)
O2	0.122 (6)	0.287 (12)	0.234 (9)	0.107 (7)	0.006 (6)	−0.103 (9)
O3	0.162 (6)	0.188 (7)	0.191 (6)	0.051 (5)	−0.001 (5)	−0.087 (6)
O4	0.086 (4)	0.132 (5)	0.223 (7)	0.024 (4)	0.093 (4)	−0.033 (5)
N1	0.0218 (15)	0.0313 (18)	0.047 (2)	−0.0011 (12)	0.0060 (14)	−0.0014 (15)
N2	0.0246 (17)	0.055 (3)	0.080 (3)	0.0071 (17)	0.0115 (18)	−0.009 (2)
N3	0.046 (3)	0.081 (4)	0.096 (4)	0.009 (3)	0.032 (3)	−0.010 (3)
C1	0.0223 (17)	0.036 (2)	0.046 (2)	0.0032 (15)	0.0096 (16)	0.0034 (17)
C2	0.0235 (17)	0.038 (2)	0.046 (2)	0.0045 (15)	0.0097 (17)	0.0011 (18)
C3	0.035 (2)	0.041 (3)	0.056 (3)	−0.0073 (18)	0.013 (2)	−0.004 (2)
C4	0.033 (2)	0.052 (3)	0.053 (3)	0.0012 (19)	0.007 (2)	−0.014 (2)
C5	0.0236 (18)	0.054 (3)	0.048 (3)	0.0068 (18)	0.0093 (18)	0.000 (2)
C6	0.039 (2)	0.072 (4)	0.053 (3)	0.010 (2)	0.015 (2)	−0.007 (3)
C7	0.041 (3)	0.093 (4)	0.051 (3)	0.017 (3)	0.025 (2)	0.008 (3)
C8	0.030 (2)	0.078 (4)	0.065 (3)	0.006 (2)	0.020 (2)	0.021 (3)
C9	0.029 (2)	0.057 (3)	0.063 (3)	0.003 (2)	0.018 (2)	0.008 (2)
C10	0.0194 (17)	0.049 (3)	0.049 (3)	0.0084 (16)	0.0103 (17)	0.0050 (19)
C11	0.0235 (18)	0.035 (2)	0.052 (3)	0.0008 (16)	0.0106 (17)	0.0072 (19)
C12	0.0222 (18)	0.038 (2)	0.062 (3)	−0.0043 (16)	0.0096 (18)	−0.011 (2)
C13	0.0254 (19)	0.049 (3)	0.058 (3)	0.0024 (18)	0.0058 (19)	−0.011 (2)
C14	0.030 (2)	0.067 (3)	0.065 (3)	0.014 (2)	0.013 (2)	−0.004 (3)
C15	0.031 (3)	0.070 (4)	0.156 (8)	0.007 (3)	−0.015 (4)	−0.016 (4)
C16	0.043 (4)	0.079 (5)	0.338 (16)	−0.010 (4)	0.019 (6)	0.054 (8)
C17	0.045 (3)	0.081 (4)	0.126 (6)	0.018 (3)	0.029 (3)	0.032 (4)
C18	0.044 (4)	0.083 (5)	0.270 (13)	−0.003 (3)	0.035 (5)	0.015 (7)

Ni1—N1i	1.743 (3)	C7—H7	0.9300
Ni1—N1	1.743 (3)	C8—C9	1.437 (7)
Ni1—O1	1.888 (3)	C8—H8	0.9300
Ni1—O1i	1.888 (3)	C9—C10	1.374 (6)
O1—C2	1.353 (5)	C9—H9	0.9300
O2—N3	1.059 (7)	C11—H11	0.9300
O3—N3	1.135 (8)	C12—C13	1.531 (6)
O4—N3	1.111 (6)	C12—H12A	0.9700
N1—C11	1.360 (5)	C12—H12B	0.9700
N1—C12	1.469 (5)	C13—C14	1.454 (6)
N2—C15	1.442 (7)	C13—H13A	0.9700
N2—C14	1.483 (7)	C13—H13B	0.9700
N2—C17	1.495 (8)	C14—H14A	0.9700
N2—H2	0.89 (6)	C14—H14B	0.9700
C1—C2	1.345 (6)	C15—C16	1.487 (12)
C1—C11	1.457 (6)	C15—H15A	0.9700
C1—C10	1.513 (6)	C15—H15B	0.9700
C2—C3	1.465 (6)	C16—H16A	0.9600
C3—C4	1.400 (7)	C16—H16B	0.9600
C3—H3	0.9300	C16—H16C	0.9600
C4—C5	1.373 (7)	C17—C18	1.428 (10)
C4—H4	0.9300	C17—H17A	0.9700
C5—C10	1.439 (6)	C17—H17B	0.9700
C5—C6	1.484 (7)	C18—H18A	0.9600
C6—C7	1.310 (8)	C18—H18B	0.9600
C6—H6	0.9300	C18—H18C	0.9600
C7—C8	1.424 (8)
N1i—Ni1—N1	180.0 (3)	C9—C10—C1	122.2 (4)
N1i—Ni1—O1	88.51 (14)	C5—C10—C1	123.4 (4)
N1—Ni1—O1	91.49 (14)	N1—C11—C1	132.3 (4)
N1i—Ni1—O1i	91.49 (14)	N1—C11—H11	113.8
N1—Ni1—O1i	88.51 (14)	C1—C11—H11	113.8
O1—Ni1—O1i	180.0 (2)	N1—C12—C13	112.1 (4)
C2—O1—Ni1	129.4 (3)	N1—C12—H12A	109.2
C11—N1—C12	123.0 (3)	C13—C12—H12A	109.2
C11—N1—Ni1	122.5 (3)	N1—C12—H12B	109.2
C12—N1—Ni1	114.4 (3)	C13—C12—H12B	109.2
C15—N2—C14	113.2 (5)	H12A—C12—H12B	107.9
C15—N2—C17	100.5 (6)	C14—C13—C12	104.3 (4)
C14—N2—C17	124.0 (4)	C14—C13—H13A	110.9
C15—N2—H2	117 (4)	C12—C13—H13A	110.9
C14—N2—H2	93 (4)	C14—C13—H13B	110.9
C17—N2—H2	110 (4)	C12—C13—H13B	110.9
O2—N3—O4	120.0 (8)	H13A—C13—H13B	108.9
O2—N3—O3	113.3 (7)	C13—C14—N2	108.0 (4)
O4—N3—O3	126.3 (7)	C13—C14—H14A	110.1
C2—C1—C11	114.7 (4)	N2—C14—H14A	110.1
C2—C1—C10	118.4 (4)	C13—C14—H14B	110.1
C11—C1—C10	126.7 (4)	N2—C14—H14B	110.1
C1—C2—O1	122.3 (4)	H14A—C14—H14B	108.4
C1—C2—C3	116.4 (4)	N2—C15—C16	103.9 (7)
O1—C2—C3	121.3 (4)	N2—C15—H15A	111.0
C4—C3—C2	125.2 (4)	C16—C15—H15A	111.0
C4—C3—H3	117.4	N2—C15—H15B	111.0
C2—C3—H3	117.4	C16—C15—H15B	111.0
C5—C4—C3	120.8 (4)	H15A—C15—H15B	109.0
C5—C4—H4	119.6	C15—C16—H16A	109.5
C3—C4—H4	119.6	C15—C16—H16B	109.5
C4—C5—C10	115.7 (4)	H16A—C16—H16B	109.5
C4—C5—C6	120.6 (5)	C15—C16—H16C	109.5
C10—C5—C6	123.7 (4)	H16A—C16—H16C	109.5
C7—C6—C5	120.3 (5)	H16B—C16—H16C	109.5
C7—C6—H6	119.8	C18—C17—N2	107.0 (7)
C5—C6—H6	119.8	C18—C17—H17A	110.3
C6—C7—C8	116.5 (5)	N2—C17—H17A	110.3
C6—C7—H7	121.8	C18—C17—H17B	110.3
C8—C7—H7	121.8	N2—C17—H17B	110.3
C7—C8—C9	124.8 (5)	H17A—C17—H17B	108.6
C7—C8—H8	117.6	C17—C18—H18A	109.5
C9—C8—H8	117.6	C17—C18—H18B	109.5
C10—C9—C8	120.4 (5)	H18A—C18—H18B	109.5
C10—C9—H9	119.8	C17—C18—H18C	109.5
C8—C9—H9	119.8	H18A—C18—H18C	109.5
C9—C10—C5	114.3 (4)	H18B—C18—H18C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O3ii	0.89 (6)	2.05 (4)	2.836 (8)	146 (6)
N2—H2···O2ii	0.89 (6)	2.17 (5)	3.033 (9)	162 (6)

Ni1—N1	1.743 (3)
Ni1—O1	1.888 (3)

N1i—Ni1—N1	180.0 (3)
N1i—Ni1—O1	88.51 (14)
N1—Ni1—O1	91.49 (14)

Symmetry code: (i) .

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O3ii	0.89 (6)	2.05 (4)	2.836 (8)	146 (6)
N2—H2⋯O2ii	0.89 (6)	2.17 (5)	3.033 (9)	162 (6)

Symmetry code: (ii) .