Bis[2-(3-cyano­phenyl­imino­meth­yl)phenolato]nickel(II)

In the title complex, [Ni(C₁₄H₉N₂O)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-cyano­phenyl­imino­meth­yl)phenolate ligands in a square-planar geometry. The dihedral angle between the cyano­phenyl and phenolate rings is 47.62 (7)°.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.034
• wR factor = 0.090
• Data-to-parameter ratio = 15.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.85
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C10    -   C14    ...       1.44 Ang.

Alert level G
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      0.849
            Tmax scaled      0.849 Tmin scaled      0.723
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

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

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

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S1. Comment

Schiff bases have been used extensively as ligands in the field of coordination chemistry. These complexes play an important role in the development of pharmacological and catalytic properties (Harrop et al., 2003; Brückner et al., 2000). Nickel(II) compounds with Schiff bases have received much attention in recent years (Marganian et al., 1995). Here we report the molecular and crystal structure of nickel (II) complex with a Schiff base ligand.

The Ni^II atom in (I) lies on an inversion center and is coordinated by the two imine N and two phenolateO atoms of the two Schiff base ligands in a square-planar geometry (Fig.1). The dihedral angle between the cyanophenyl and phenyl rings is 47.62 (7)°.. The Ni—O and Ni—N bond lengths agree with the values reported for related complexes(Peng, et al., (2006); Adams et al., 2004; Bian et al., 2004).

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).

S2. Experimental

2-(3-cyanophenyliminomethyl)phenol was prepared according to the literature (Akkurt et al., 2006). NiCl₂.6H₂O(23.7 mg, 0.1 mmol) in methanol (5 ml) was added to the solution of 2-(3-cyanophenyliminomethyl)phenol (22.2 mg, 0.1 mmol)in the methanol (5 ml), the pH was then adjusted to 8–9 and the mixture was stirred for 4 h. The filtrate was kept at room temperature for about two weeks, and blue block shaped crystals of (I) suitable for for X-ray single-crystal analyses were obtained.

S3. Refinement

All H atoms attached to C atoms were fixed geometrically and treated as riding with C—H = 0.93 Å and U_iso(H) = 1.2U_eq(C).

Computing details

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); 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 (Sheldrick, 2008).

Figures

Fig. 1. Molecular view of the title compound with the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented as small spheres of arbitrary radii. [Symmetry code: (i) 1 - x, 1 - y, 1 - z]

Bis[2-(3-cyanophenyliminomethyl)phenolato]nickel(II)

Crystal data

[Ni(C14H9N2O)2]	F(000) = 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 = 3.1–27.4°
b = 8.0856 (16) Å	µ = 0.91 mm^−1
c = 15.644 (3) Å	T = 293 K
β = 104.01 (3)°	Block, blue
V = 1108.1 (4) Å^3	0.25 × 0.18 × 0.18 mm
Z = 2

Data collection

Rigaku Mercury2 diffractometer	2540 independent reflections
Radiation source: fine-focus sealed tube	2246 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.035
Detector resolution: 13.6612 pixels mm^-1	θmax = 27.5°, θmin = 3.1°
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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.090	H-atom parameters constrained
S = 1.10	w = 1/[σ^2(Fo^2) + (0.0403P)^2 + 0.5389P] where P = (Fo^2 + 2Fc^2)/3
2540 reflections	(Δ/σ)max < 0.001
160 parameters	Δρmax = 0.32 e Å^−3
0 restraints	Δρmin = −0.35 e Å^−3

Special details

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 (Ų)

	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*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

Geometric parameters (Å, º)

Ni1—O1^i	1.8310 (14)	C8—C13	1.378 (3)
Ni1—O1	1.8310 (14)	C11—C12	1.371 (3)
Ni1—N1^i	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)
O1^i—Ni1—O1	180.000 (1)	C10—C11—H11	120.4
O1^i—Ni1—N1^i	92.65 (6)	C4—C3—C2	120.89 (19)
O1—Ni1—N1^i	87.35 (6)	C4—C3—H3	119.6
O1^i—Ni1—N1	87.35 (6)	C2—C3—H3	119.6
O1—Ni1—N1	92.65 (6)	O1—C2—C1	123.56 (17)
N1^i—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

Symmetry code: (i) −x+1, −y+1, −z+1.