{2,2′-[4-Chloro-5-methyl-o-phenyl­enebis(nitrilo­methyl­idyne)]diphenolato}nickel(II)

Wang, H.

doi:10.1107/S1600536810046088

metal-organic compounds

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Volume 66| Part 12| December 2010| Page m1571

https://doi.org/10.1107/S1600536810046088

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{2,2′-[4-Chloro-5-methyl-o-phenylenebis(nitrilomethylidyne)]diphenolato}nickel(II)

Haixia Wang ^a ^*

^aDepartment of Chemistry and Environmental Science, Henan Normal University, Xinxiang 453007, People's Republic of China
^*Correspondence e-mail: xxhxwang@126.com

(Received 31 October 2010; accepted 9 November 2010; online 13 November 2010)

In the title complex, [Ni(C₂₁H₁₅ClN₂O₂)], the Ni^II ion is coordinated by two N and two O atoms from the tetradentate Schiff base ligand in a distorted square geometry. The crystal packing exhibits short intermolecular Ni⋯Ni distances of 3.273 (3) Å.

Related literature

For related structures, see: Ali et al. (2010 ); Hernandez-Molina et al. (1997 ); Niu et al. (2009 ); Radha et al. (1985 ).

Experimental

Crystal data

[Ni(C₂₁H₁₅ClN₂O₂)]
M_r = 421.51
Monoclinic, P 2₁ /c
a = 11.0451 (10) Å
b = 8.0202 (7) Å
c = 19.5959 (17) Å
β = 106.37°
V = 1665.5 (3) Å³
Z = 4
Mo Kα radiation
μ = 1.35 mm⁻¹
T = 293 K
0.34 × 0.29 × 0.23 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ) T_min = 0.658, T_max = 0.747
7946 measured reflections
2917 independent reflections
2155 reflections with I > 2σ(I)
R_int = 0.040

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.153
S = 1.03
2917 reflections
245 parameters
H-atom parameters constrained
Δρ_max = 0.67 e Å⁻³
Δρ_min = −0.91 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT-Plus (Bruker, 2001 ); data reduction: SAINT-Plus; 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810046088/cv2792sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810046088/cv2792Isup2.hkl

checkCIF report

Comment top

Schiff-base ligands, due to their excellent coordination ability, have been widely introduced into the coordination chemistry. Here, we report a new nickel complex based on a tetradentate Schiff-base ligand.

In the title compound (Fig. 1), the whole molecule is essentially planar with the mean deviation 0.0523 Å from the plane formed by all non-hydrogen atoms. The Ni^II ion is four-coordinated by two N atoms and two O atoms of the Schiff base ligand. The Ni—O and Ni—N bond lengths are all consistent with those found in other reported tetradentate Schiff base Ni complexes (Ali, et al., 2010; Hernandez-Molina, et al., 1997; Niu, et al., 2009; Radha, et al., 1985).

Related literature top

For related structures, see: Ali et al. (2010); Hernandez-Molina et al. (1997); Niu et al. (2009); Radha et al. (1985).

Experimental top

The synthesis of the title complex was carried out by reaction of Ni(ClO₄)₂.6H₂O and the Schiff-base ligand with the molar ratio 1:1 in methanol under the stirring condition at room temperature. The filtrated solution was left to slowly evaperate in air to obtain single-crystal suitable for X-ray diffraction with the yield about 56%.

Structure description top

For related structures, see: Ali et al. (2010); Hernandez-Molina et al. (1997); Niu et al. (2009); Radha et al. (1985).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); 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 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title complex with the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms omitted for clarity.

{2,2'-[4-Chloro-5-methyl-o- phenylenebis(nitrilomethylidyne)]diphenolato}nickel(II) top

Crystal data top

[Ni(C₂₁H₁₅ClN₂O₂)]	F(000) = 864
M_r = 421.51	D_x = 1.681 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2314 reflections
a = 11.0451 (10) Å	θ = 2.5–27.0°
b = 8.0202 (7) Å	µ = 1.35 mm⁻¹
c = 19.5959 (17) Å	T = 293 K
β = 106.37°	Block, red-brown
V = 1665.5 (3) Å³	0.34 × 0.29 × 0.23 mm
Z = 4

Data collection top

Bruker APEXII CCD area-detector diffractometer	2917 independent reflections
Radiation source: fine-focus sealed tube	2155 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.040
φ and ω scans	θ_max = 25.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	h = −13→13
T_min = 0.658, T_max = 0.747	k = −9→9
7946 measured reflections	l = −23→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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.153	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.1P)²] where P = (F_o² + 2F_c²)/3
2917 reflections	(Δ/σ)_max = 0.018
245 parameters	Δρ_max = 0.67 e Å⁻³
0 restraints	Δρ_min = −0.91 e Å⁻³

Crystal data top

[Ni(C₂₁H₁₅ClN₂O₂)]	V = 1665.5 (3) Å³
M_r = 421.51	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.0451 (10) Å	µ = 1.35 mm⁻¹
b = 8.0202 (7) Å	T = 293 K
c = 19.5959 (17) Å	0.34 × 0.29 × 0.23 mm
β = 106.37°

Data collection top

Bruker APEXII CCD area-detector diffractometer	2917 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	2155 reflections with I > 2σ(I)
T_min = 0.658, T_max = 0.747	R_int = 0.040
7946 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.153	H-atom parameters constrained
S = 1.03	Δρ_max = 0.67 e Å⁻³
2917 reflections	Δρ_min = −0.91 e Å⁻³
245 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	0.45347 (5)	0.83377 (6)	0.03397 (2)	0.0490 (2)
Cl1	0.13615 (17)	0.8003 (2)	−0.31318 (8)	0.1129 (6)
O1	0.4706 (3)	0.9080 (4)	0.12480 (13)	0.0619 (7)
O2	0.6066 (3)	0.7335 (4)	0.07528 (14)	0.0582 (7)
N1	0.2996 (3)	0.9374 (4)	−0.00538 (16)	0.0520 (8)
N2	0.4388 (3)	0.7559 (4)	−0.05774 (15)	0.0471 (8)
C1	0.2514 (4)	0.9118 (5)	−0.0800 (2)	0.0541 (10)
C2	0.3286 (4)	0.8106 (5)	−0.1080 (2)	0.0531 (10)
C3	0.2928 (4)	0.7764 (6)	−0.1805 (2)	0.0627 (11)
H3	0.3430	0.7089	−0.1999	0.075*
C4	0.1837 (5)	0.8422 (6)	−0.2230 (2)	0.0732 (14)
C5	0.1058 (5)	0.9433 (6)	−0.1956 (3)	0.0721 (13)
C6	0.1415 (4)	0.9765 (6)	−0.1252 (2)	0.0689 (12)
H6	0.0908	1.0449	−0.1065	0.083*
C7	0.2348 (4)	1.0221 (5)	0.0289 (2)	0.0583 (11)
H7	0.1561	1.0618	0.0031	0.070*
C8	0.2758 (4)	1.0584 (5)	0.1032 (2)	0.0606 (11)
C9	0.1979 (6)	1.1596 (6)	0.1325 (3)	0.0792 (15)
H9	0.1203	1.1955	0.1035	0.095*
C10	0.2337 (7)	1.2052 (7)	0.2016 (3)	0.0926 (18)
H10	0.1801	1.2683	0.2204	0.111*
C11	0.3516 (7)	1.1567 (7)	0.2444 (3)	0.0880 (18)
H11	0.3779	1.1922	0.2915	0.106*
C12	0.4299 (5)	1.0572 (6)	0.2186 (2)	0.0756 (14)
H12	0.5079	1.0253	0.2484	0.091*
C13	0.3926 (5)	1.0026 (5)	0.1465 (2)	0.0598 (11)
C14	0.5194 (4)	0.6572 (5)	−0.0743 (2)	0.0530 (10)
H14	0.4997	0.6228	−0.1215	0.064*
C15	0.6325 (4)	0.5970 (5)	−0.0291 (2)	0.0529 (10)
C16	0.7113 (5)	0.4956 (5)	−0.0562 (3)	0.0669 (12)
H16	0.6855	0.4652	−0.1039	0.080*
C17	0.8255 (5)	0.4398 (6)	−0.0143 (3)	0.0774 (14)
H17	0.8756	0.3714	−0.0334	0.093*
C18	0.8657 (5)	0.4859 (6)	0.0564 (3)	0.0752 (13)
H18	0.9440	0.4507	0.0847	0.090*
C19	0.7894 (4)	0.5848 (6)	0.0855 (2)	0.0676 (12)
H19	0.8173	0.6124	0.1335	0.081*
C20	0.6729 (4)	0.6436 (5)	0.0451 (2)	0.0529 (10)
C21	0.0008 (6)	1.0115 (12)	−0.2558 (4)	0.132 (3)
H21A	−0.0784	0.9956	−0.2455	0.199*
H21B	−0.0005	0.9539	−0.2989	0.199*
H21C	0.0144	1.1283	−0.2613	0.199*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0643 (4)	0.0489 (4)	0.0354 (3)	−0.0117 (2)	0.0164 (2)	−0.0002 (2)
Cl1	0.1186 (13)	0.1466 (16)	0.0594 (9)	−0.0027 (10)	0.0020 (8)	−0.0031 (8)
O1	0.081 (2)	0.0689 (19)	0.0377 (15)	−0.0039 (16)	0.0190 (14)	−0.0014 (14)
O2	0.0714 (19)	0.0603 (17)	0.0423 (15)	−0.0052 (15)	0.0147 (14)	−0.0016 (13)
N1	0.072 (2)	0.0443 (18)	0.0400 (17)	−0.0150 (16)	0.0156 (15)	0.0010 (14)
N2	0.063 (2)	0.0462 (18)	0.0342 (16)	−0.0094 (16)	0.0174 (15)	0.0023 (14)
C1	0.062 (3)	0.051 (2)	0.049 (2)	−0.011 (2)	0.014 (2)	0.0046 (19)
C2	0.065 (3)	0.052 (2)	0.040 (2)	−0.0162 (19)	0.0116 (19)	0.0027 (17)
C3	0.076 (3)	0.065 (3)	0.046 (2)	−0.012 (2)	0.016 (2)	−0.003 (2)
C4	0.079 (3)	0.079 (3)	0.050 (3)	−0.019 (3)	−0.001 (2)	0.013 (2)
C5	0.074 (3)	0.071 (3)	0.062 (3)	−0.007 (3)	0.003 (2)	0.004 (2)
C6	0.073 (3)	0.065 (3)	0.066 (3)	−0.008 (2)	0.016 (2)	0.003 (2)
C7	0.070 (3)	0.049 (2)	0.061 (3)	−0.010 (2)	0.026 (2)	0.001 (2)
C8	0.086 (3)	0.048 (2)	0.057 (3)	−0.013 (2)	0.035 (2)	−0.001 (2)
C9	0.103 (4)	0.065 (3)	0.082 (4)	0.001 (3)	0.047 (3)	−0.002 (2)
C10	0.142 (6)	0.073 (3)	0.085 (4)	−0.008 (4)	0.068 (4)	−0.017 (3)
C11	0.141 (5)	0.077 (4)	0.061 (3)	−0.028 (3)	0.053 (4)	−0.017 (3)
C12	0.111 (4)	0.075 (3)	0.047 (2)	−0.019 (3)	0.035 (3)	−0.008 (2)
C13	0.090 (3)	0.050 (2)	0.046 (2)	−0.021 (2)	0.032 (2)	−0.0019 (19)
C14	0.075 (3)	0.047 (2)	0.039 (2)	−0.016 (2)	0.019 (2)	0.0006 (17)
C15	0.067 (3)	0.044 (2)	0.053 (2)	−0.0125 (19)	0.027 (2)	0.0010 (18)
C16	0.084 (3)	0.055 (3)	0.065 (3)	−0.007 (2)	0.028 (3)	0.005 (2)
C17	0.090 (4)	0.059 (3)	0.094 (4)	−0.004 (3)	0.044 (3)	0.003 (3)
C18	0.069 (3)	0.069 (3)	0.088 (4)	−0.004 (2)	0.022 (3)	0.009 (3)
C19	0.071 (3)	0.069 (3)	0.060 (3)	−0.012 (2)	0.013 (2)	0.005 (2)
C20	0.064 (3)	0.044 (2)	0.053 (2)	−0.0135 (19)	0.020 (2)	0.0092 (18)
C21	0.099 (5)	0.161 (8)	0.116 (5)	−0.012 (4)	−0.004 (4)	0.020 (4)

Geometric parameters (Å, º) top

Ni1—O1	1.835 (3)	C9—C10	1.349 (8)
Ni1—O2	1.841 (3)	C9—H9	0.9300
Ni1—N1	1.854 (3)	C10—C11	1.391 (8)
Ni1—N2	1.866 (3)	C10—H10	0.9300
Cl1—C4	1.729 (5)	C11—C12	1.375 (7)
O1—C13	1.306 (5)	C11—H11	0.9300
O2—C20	1.285 (5)	C12—C13	1.425 (6)
N1—C7	1.302 (5)	C12—H12	0.9300
N1—C1	1.422 (5)	C14—C15	1.398 (6)
N2—C14	1.298 (5)	C14—H14	0.9300
N2—C2	1.403 (5)	C15—C16	1.400 (6)
C1—C6	1.386 (6)	C15—C20	1.444 (6)
C1—C2	1.397 (6)	C16—C17	1.372 (7)
C2—C3	1.390 (6)	C16—H16	0.9300
C3—C4	1.363 (6)	C17—C18	1.381 (7)
C3—H3	0.9300	C17—H17	0.9300
C4—C5	1.395 (7)	C18—C19	1.390 (7)
C5—C6	1.349 (6)	C18—H18	0.9300
C5—C21	1.505 (8)	C19—C20	1.390 (6)
C6—H6	0.9300	C19—H19	0.9300
C7—C8	1.428 (6)	C21—H21A	0.9600
C7—H7	0.9300	C21—H21B	0.9600
C8—C13	1.402 (6)	C21—H21C	0.9600
C8—C9	1.417 (6)

O1—Ni1—O2	83.34 (13)	C8—C9—H9	119.3
O1—Ni1—N1	95.17 (14)	C9—C10—C11	119.3 (5)
O2—Ni1—N1	178.50 (13)	C9—C10—H10	120.3
O1—Ni1—N2	178.89 (14)	C11—C10—H10	120.3
O2—Ni1—N2	95.55 (14)	C12—C11—C10	121.3 (5)
N1—Ni1—N2	85.94 (14)	C12—C11—H11	119.4
C13—O1—Ni1	127.3 (3)	C10—C11—H11	119.4
C20—O2—Ni1	127.9 (3)	C11—C12—C13	120.5 (5)
C7—N1—C1	120.3 (4)	C11—C12—H12	119.7
C7—N1—Ni1	126.3 (3)	C13—C12—H12	119.7
C1—N1—Ni1	113.4 (3)	O1—C13—C8	124.6 (4)
C14—N2—C2	122.4 (3)	O1—C13—C12	117.9 (5)
C14—N2—Ni1	124.4 (3)	C8—C13—C12	117.5 (4)
C2—N2—Ni1	113.2 (3)	N2—C14—C15	127.2 (4)
C6—C1—C2	119.2 (4)	N2—C14—H14	116.4
C6—C1—N1	127.6 (4)	C15—C14—H14	116.4
C2—C1—N1	113.2 (4)	C14—C15—C16	120.0 (4)
C3—C2—C1	119.1 (4)	C14—C15—C20	121.0 (4)
C3—C2—N2	126.6 (4)	C16—C15—C20	118.9 (4)
C1—C2—N2	114.3 (3)	C17—C16—C15	121.8 (5)
C4—C3—C2	119.8 (5)	C17—C16—H16	119.1
C4—C3—H3	120.1	C15—C16—H16	119.1
C2—C3—H3	120.1	C16—C17—C18	119.6 (5)
C3—C4—C5	121.6 (4)	C16—C17—H17	120.2
C3—C4—Cl1	120.7 (4)	C18—C17—H17	120.2
C5—C4—Cl1	117.6 (4)	C17—C18—C19	120.2 (5)
C6—C5—C4	118.3 (5)	C17—C18—H18	119.9
C6—C5—C21	131.9 (6)	C19—C18—H18	119.9
C4—C5—C21	109.4 (5)	C18—C19—C20	122.0 (5)
C5—C6—C1	122.1 (5)	C18—C19—H19	119.0
C5—C6—H6	119.0	C20—C19—H19	119.0
C1—C6—H6	119.0	O2—C20—C19	119.0 (4)
N1—C7—C8	124.8 (4)	O2—C20—C15	123.6 (4)
N1—C7—H7	117.6	C19—C20—C15	117.4 (4)
C8—C7—H7	117.6	C5—C21—H21A	109.5
C13—C8—C9	119.9 (4)	C5—C21—H21B	109.5
C13—C8—C7	121.6 (4)	H21A—C21—H21B	109.5
C9—C8—C7	118.4 (5)	C5—C21—H21C	109.5
C10—C9—C8	121.4 (6)	H21A—C21—H21C	109.5
C10—C9—H9	119.3	H21B—C21—H21C	109.5

Experimental details

Crystal data
Chemical formula	[Ni(C₂₁H₁₅ClN₂O₂)]
M_r	421.51
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	11.0451 (10), 8.0202 (7), 19.5959 (17)
β (°)	106.37
V (Å³)	1665.5 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.35
Crystal size (mm)	0.34 × 0.29 × 0.23

Data collection
Diffractometer	Bruker APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 2007)
T_min, T_max	0.658, 0.747
No. of measured, independent and observed [I > 2σ(I)] reflections	7946, 2917, 2155
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.153, 1.03
No. of reflections	2917
No. of parameters	245
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.67, −0.91

Computer programs: APEX2 (Bruker, 2004), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

References

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