Bis[2-(3-cyano-phenyl-imino-meth-yl)phenolato]nickel(II).

In the title complex, [Ni(C(14)H(9)N(2)O)(2)], the Ni(II) atom lies on an inversion center and is coordinated by the O atom and an N atom of two Schiff base 2-(3-cyano-phenyl-imino-meth-yl)phenolate ligands in a square-planar geometry. The dihedral angle between the cyano-phenyl and phenolate rings is 47.62 (7)°.

Related literature

For related literature, see: Adams et al. (2004 ▶); Bian et al. (2004 ▶); Brückner et al. (2000 ▶); Harrop et al. (2003 ▶); Marganian et al. (1995 ▶); Akkurt et al. (2006 ▶); Peng et al. (2006 ▶).

Experimental

Crystal data

[Ni(C14H9N2O)2]

M = 501.17

Monoclinic,

a = 9.0294 (18) Å

b = 8.0856 (16) Å

c = 15.644 (3) Å

β = 104.01 (3)°

V = 1108.1 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.91 mm−1

T = 293 (2) K

0.25 × 0.18 × 0.18 mm

Data collection

Rigaku Mercury2 diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.852, T max = 1.00 (expected range = 0.723–0.849)

11052 measured reflections

2540 independent reflections

2246 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.090

S = 1.10

2540 reflections

160 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.35 e Å−3

Data collection: CrystalClear (Rigaku, 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: ORTEPIII (Burnett & Johnson, 1996 ▶) and ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808004765/dn2310sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808004765/dn2310Isup2.hkl

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

[Ni(C14H9N2O1)2]	F000 = 516
Mr = 501.17	Dx = 1.502 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 10336 reflections
a = 9.0294 (18) Å	θ = 3.1–27.4º
b = 8.0856 (16) Å	µ = 0.91 mm−1
c = 15.644 (3) Å	T = 293 (2) K
β = 104.01 (3)º	Block, blue
V = 1108.1 (4) Å3	0.25 × 0.18 × 0.18 mm
Z = 2

Rigaku Mercury2 diffractometer	2540 independent reflections
Radiation source: fine-focus sealed tube	2246 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.035
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5º
T = 293(2) K	θmin = 3.1º
ω scans	h = −11→11
Absorption correction: multi-scan(CrystalClear; Rigaku, 2005)	k = −10→10
Tmin = 0.852, Tmax = 1.00	l = −20→20
11052 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.034	H-atom parameters constrained
wR(F2) = 0.090	w = 1/[σ2(Fo2) + (0.0403P)2 + 0.5389P] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max < 0.001
2540 reflections	Δρmax = 0.32 e Å−3
160 parameters	Δρmin = −0.35 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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	0.5000	0.5000	0.5000	0.02514 (11)
O1	0.66446 (15)	0.36034 (17)	0.52053 (9)	0.0349 (3)
N1	0.41172 (16)	0.38940 (18)	0.58415 (10)	0.0266 (3)
C9	0.3215 (2)	0.6210 (2)	0.65595 (12)	0.0302 (4)
H9	0.4159	0.6714	0.6613	0.036*
C14	0.2380 (2)	0.8635 (3)	0.72431 (15)	0.0401 (5)
C1	0.5678 (2)	0.1429 (2)	0.59534 (12)	0.0283 (4)
C10	0.2087 (2)	0.6997 (2)	0.68770 (12)	0.0318 (4)
C8	0.2929 (2)	0.4678 (2)	0.61652 (12)	0.0274 (4)
C11	0.0679 (2)	0.6238 (3)	0.68133 (14)	0.0395 (5)
H11	−0.0069	0.6759	0.7034	0.047*
C3	0.7949 (2)	0.1080 (3)	0.54150 (14)	0.0383 (5)
H3	0.8663	0.1492	0.5130	0.046*
C2	0.6729 (2)	0.2098 (2)	0.55130 (11)	0.0286 (4)
C13	0.1528 (2)	0.3938 (3)	0.60894 (15)	0.0404 (5)
H13	0.1329	0.2914	0.5815	0.048*
C7	0.4475 (2)	0.2409 (2)	0.61321 (12)	0.0297 (4)
H7	0.3897	0.1942	0.6488	0.036*
C5	0.7059 (3)	−0.1167 (3)	0.61697 (15)	0.0432 (5)
H5	0.7169	−0.2245	0.6382	0.052*
N2	0.2618 (3)	0.9944 (2)	0.75059 (17)	0.0570 (6)
C12	0.0409 (2)	0.4716 (3)	0.64212 (17)	0.0461 (6)
H12	−0.0527	0.4199	0.6377	0.055*
C4	0.8094 (3)	−0.0502 (3)	0.57343 (15)	0.0430 (5)
H4	0.8904	−0.1149	0.5658	0.052*
C6	0.5875 (3)	−0.0197 (2)	0.62794 (14)	0.0366 (4)
H6	0.5184	−0.0625	0.6577	0.044*

	U11	U22	U33	U12	U13	U23
Ni1	0.02507 (18)	0.02233 (17)	0.03093 (19)	0.00178 (12)	0.01241 (13)	0.00362 (12)
O1	0.0309 (7)	0.0327 (7)	0.0458 (8)	0.0070 (6)	0.0182 (6)	0.0125 (6)
N1	0.0262 (7)	0.0245 (7)	0.0319 (7)	−0.0009 (6)	0.0124 (6)	−0.0003 (6)
C9	0.0294 (9)	0.0286 (9)	0.0360 (9)	−0.0003 (7)	0.0146 (8)	0.0016 (7)
C14	0.0431 (12)	0.0363 (12)	0.0480 (12)	0.0067 (9)	0.0247 (10)	0.0000 (9)
C1	0.0305 (9)	0.0236 (9)	0.0309 (9)	0.0009 (7)	0.0075 (7)	0.0007 (7)
C10	0.0348 (10)	0.0305 (9)	0.0332 (9)	0.0058 (8)	0.0140 (8)	0.0022 (8)
C8	0.0282 (9)	0.0272 (9)	0.0300 (9)	0.0015 (7)	0.0133 (7)	0.0023 (7)
C11	0.0327 (10)	0.0449 (12)	0.0461 (11)	0.0093 (9)	0.0194 (9)	0.0032 (9)
C3	0.0335 (10)	0.0412 (11)	0.0425 (11)	0.0088 (9)	0.0134 (9)	0.0043 (9)
C2	0.0294 (9)	0.0282 (9)	0.0278 (9)	0.0036 (7)	0.0064 (7)	0.0020 (7)
C13	0.0348 (10)	0.0378 (11)	0.0521 (12)	−0.0068 (9)	0.0174 (9)	−0.0090 (9)
C7	0.0315 (9)	0.0263 (9)	0.0335 (9)	−0.0034 (7)	0.0122 (7)	0.0022 (7)
C5	0.0491 (13)	0.0250 (10)	0.0528 (13)	0.0073 (9)	0.0070 (10)	0.0048 (9)
N2	0.0685 (15)	0.0369 (11)	0.0762 (15)	−0.0001 (9)	0.0379 (12)	−0.0109 (10)
C12	0.0294 (10)	0.0550 (14)	0.0592 (14)	−0.0081 (9)	0.0212 (10)	−0.0084 (11)
C4	0.0407 (12)	0.0397 (11)	0.0476 (12)	0.0173 (9)	0.0085 (9)	0.0018 (10)
C6	0.0398 (11)	0.0266 (10)	0.0437 (11)	−0.0013 (8)	0.0104 (9)	0.0045 (8)

Ni1—O1i	1.8310 (14)	C8—C13	1.378 (3)
Ni1—O1	1.8310 (14)	C11—C12	1.371 (3)
Ni1—N1i	1.9174 (15)	C11—H11	0.9300
Ni1—N1	1.9174 (15)	C3—C4	1.368 (3)
O1—C2	1.304 (2)	C3—C2	1.413 (3)
N1—C7	1.297 (2)	C3—H3	0.9300
N1—C8	1.440 (2)	C13—C12	1.393 (3)
C9—C8	1.380 (3)	C13—H13	0.9300
C9—C10	1.391 (3)	C7—H7	0.9300
C9—H9	0.9300	C5—C6	1.370 (3)
C14—N2	1.137 (3)	C5—C4	1.390 (3)
C14—C10	1.442 (3)	C5—H5	0.9300
C1—C6	1.406 (2)	C12—H12	0.9300
C1—C2	1.409 (3)	C4—H4	0.9300
C1—C7	1.426 (3)	C6—H6	0.9300
C10—C11	1.393 (3)
O1i—Ni1—O1	180.000 (1)	C10—C11—H11	120.4
O1i—Ni1—N1i	92.65 (6)	C4—C3—C2	120.89 (19)
O1—Ni1—N1i	87.35 (6)	C4—C3—H3	119.6
O1i—Ni1—N1	87.35 (6)	C2—C3—H3	119.6
O1—Ni1—N1	92.65 (6)	O1—C2—C1	123.56 (17)
N1i—Ni1—N1	180.000 (1)	O1—C2—C3	118.75 (17)
C2—O1—Ni1	127.78 (12)	C1—C2—C3	117.68 (17)
C7—N1—C8	115.34 (15)	C8—C13—C12	120.4 (2)
C7—N1—Ni1	124.25 (13)	C8—C13—H13	119.8
C8—N1—Ni1	120.35 (12)	C12—C13—H13	119.8
C8—C9—C10	119.75 (18)	N1—C7—C1	125.63 (17)
C8—C9—H9	120.1	N1—C7—H7	117.2
C10—C9—H9	120.1	C1—C7—H7	117.2
N2—C14—C10	177.8 (2)	C6—C5—C4	118.5 (2)
C6—C1—C2	119.71 (18)	C6—C5—H5	120.7
C6—C1—C7	118.93 (18)	C4—C5—H5	120.7
C2—C1—C7	121.21 (16)	C11—C12—C13	120.4 (2)
C9—C10—C11	120.51 (18)	C11—C12—H12	119.8
C9—C10—C14	118.81 (18)	C13—C12—H12	119.8
C11—C10—C14	120.64 (18)	C3—C4—C5	121.6 (2)
C13—C8—C9	119.78 (17)	C3—C4—H4	119.2
C13—C8—N1	121.69 (17)	C5—C4—H4	119.2
C9—C8—N1	118.53 (16)	C5—C6—C1	121.6 (2)
C12—C11—C10	119.20 (19)	C5—C6—H6	119.2
C12—C11—H11	120.4	C1—C6—H6	119.2