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Acta Crystallogr Sect E Struct Rep Online. 2010 December 1; 66(Pt 12): m1571.
Published online 2010 November 13. doi:  10.1107/S1600536810046088
PMCID: PMC3011529

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

Abstract

In the title complex, [Ni(C21H15ClN2O2)], the NiII 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 [triangle]); Hernandez-Molina et al. (1997 [triangle]); Niu et al. (2009 [triangle]); Radha et al. (1985 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-m1571-scheme1.jpg

Experimental

Crystal data

  • [Ni(C21H15ClN2O2)]
  • M r = 421.51
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-m1571-efi1.jpg
  • 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 [triangle]) 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[F 2 > 2σ(F 2)] = 0.052
  • wR(F 2) = 0.153
  • S = 1.03
  • 2917 reflections
  • 245 parameters
  • H-atom parameters constrained
  • Δρmax = 0.67 e Å−3
  • Δρmin = −0.91 e Å−3

Data collection: APEX2 (Bruker, 2004 [triangle]); cell refinement: SAINT-Plus (Bruker, 2001 [triangle]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Supplementary Material

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

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810046088/cv2792Isup2.hkl

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

supplementary crystallographic information

Comment

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 NiII 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).

Experimental

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%.

Refinement

C-bound H atoms were placed in idealized positions with C—H distances of 0.93 and 0.96 Å, and were refined as riding atoms, with Uiso(H) = 1.2-1.5 Ueq(C).

Figures

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.

Crystal data

[Ni(C21H15ClN2O2)]F(000) = 864
Mr = 421.51Dx = 1.681 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2314 reflections
a = 11.0451 (10) Åθ = 2.5–27.0°
b = 8.0202 (7) ŵ = 1.35 mm1
c = 19.5959 (17) ÅT = 293 K
β = 106.37°Block, red-brown
V = 1665.5 (3) Å30.34 × 0.29 × 0.23 mm
Z = 4

Data collection

Bruker APEXII CCD area-detector diffractometer2917 independent reflections
Radiation source: fine-focus sealed tube2155 reflections with I > 2σ(I)
graphiteRint = 0.040
[var phi] and ω scansθmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)h = −13→13
Tmin = 0.658, Tmax = 0.747k = −9→9
7946 measured reflectionsl = −23→19

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.052Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.153H-atom parameters constrained
S = 1.02w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3
2917 reflections(Δ/σ)max = 0.018
245 parametersΔρmax = 0.67 e Å3
0 restraintsΔρmin = −0.91 e Å3

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 (Å2)

xyzUiso*/Ueq
Ni10.45347 (5)0.83377 (6)0.03397 (2)0.0490 (2)
Cl10.13615 (17)0.8003 (2)−0.31318 (8)0.1129 (6)
O10.4706 (3)0.9080 (4)0.12480 (13)0.0619 (7)
O20.6066 (3)0.7335 (4)0.07528 (14)0.0582 (7)
N10.2996 (3)0.9374 (4)−0.00538 (16)0.0520 (8)
N20.4388 (3)0.7559 (4)−0.05774 (15)0.0471 (8)
C10.2514 (4)0.9118 (5)−0.0800 (2)0.0541 (10)
C20.3286 (4)0.8106 (5)−0.1080 (2)0.0531 (10)
C30.2928 (4)0.7764 (6)−0.1805 (2)0.0627 (11)
H30.34300.7089−0.19990.075*
C40.1837 (5)0.8422 (6)−0.2230 (2)0.0732 (14)
C50.1058 (5)0.9433 (6)−0.1956 (3)0.0721 (13)
C60.1415 (4)0.9765 (6)−0.1252 (2)0.0689 (12)
H60.09081.0449−0.10650.083*
C70.2348 (4)1.0221 (5)0.0289 (2)0.0583 (11)
H70.15611.06180.00310.070*
C80.2758 (4)1.0584 (5)0.1032 (2)0.0606 (11)
C90.1979 (6)1.1596 (6)0.1325 (3)0.0792 (15)
H90.12031.19550.10350.095*
C100.2337 (7)1.2052 (7)0.2016 (3)0.0926 (18)
H100.18011.26830.22040.111*
C110.3516 (7)1.1567 (7)0.2444 (3)0.0880 (18)
H110.37791.19220.29150.106*
C120.4299 (5)1.0572 (6)0.2186 (2)0.0756 (14)
H120.50791.02530.24840.091*
C130.3926 (5)1.0026 (5)0.1465 (2)0.0598 (11)
C140.5194 (4)0.6572 (5)−0.0743 (2)0.0530 (10)
H140.49970.6228−0.12150.064*
C150.6325 (4)0.5970 (5)−0.0291 (2)0.0529 (10)
C160.7113 (5)0.4956 (5)−0.0562 (3)0.0669 (12)
H160.68550.4652−0.10390.080*
C170.8255 (5)0.4398 (6)−0.0143 (3)0.0774 (14)
H170.87560.3714−0.03340.093*
C180.8657 (5)0.4859 (6)0.0564 (3)0.0752 (13)
H180.94400.45070.08470.090*
C190.7894 (4)0.5848 (6)0.0855 (2)0.0676 (12)
H190.81730.61240.13350.081*
C200.6729 (4)0.6436 (5)0.0451 (2)0.0529 (10)
C210.0008 (6)1.0115 (12)−0.2558 (4)0.132 (3)
H21A−0.07840.9956−0.24550.199*
H21B−0.00050.9539−0.29890.199*
H21C0.01441.1283−0.26130.199*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Ni10.0643 (4)0.0489 (4)0.0354 (3)−0.0117 (2)0.0164 (2)−0.0002 (2)
Cl10.1186 (13)0.1466 (16)0.0594 (9)−0.0027 (10)0.0020 (8)−0.0031 (8)
O10.081 (2)0.0689 (19)0.0377 (15)−0.0039 (16)0.0190 (14)−0.0014 (14)
O20.0714 (19)0.0603 (17)0.0423 (15)−0.0052 (15)0.0147 (14)−0.0016 (13)
N10.072 (2)0.0443 (18)0.0400 (17)−0.0150 (16)0.0156 (15)0.0010 (14)
N20.063 (2)0.0462 (18)0.0342 (16)−0.0094 (16)0.0174 (15)0.0023 (14)
C10.062 (3)0.051 (2)0.049 (2)−0.011 (2)0.014 (2)0.0046 (19)
C20.065 (3)0.052 (2)0.040 (2)−0.0162 (19)0.0116 (19)0.0027 (17)
C30.076 (3)0.065 (3)0.046 (2)−0.012 (2)0.016 (2)−0.003 (2)
C40.079 (3)0.079 (3)0.050 (3)−0.019 (3)−0.001 (2)0.013 (2)
C50.074 (3)0.071 (3)0.062 (3)−0.007 (3)0.003 (2)0.004 (2)
C60.073 (3)0.065 (3)0.066 (3)−0.008 (2)0.016 (2)0.003 (2)
C70.070 (3)0.049 (2)0.061 (3)−0.010 (2)0.026 (2)0.001 (2)
C80.086 (3)0.048 (2)0.057 (3)−0.013 (2)0.035 (2)−0.001 (2)
C90.103 (4)0.065 (3)0.082 (4)0.001 (3)0.047 (3)−0.002 (2)
C100.142 (6)0.073 (3)0.085 (4)−0.008 (4)0.068 (4)−0.017 (3)
C110.141 (5)0.077 (4)0.061 (3)−0.028 (3)0.053 (4)−0.017 (3)
C120.111 (4)0.075 (3)0.047 (2)−0.019 (3)0.035 (3)−0.008 (2)
C130.090 (3)0.050 (2)0.046 (2)−0.021 (2)0.032 (2)−0.0019 (19)
C140.075 (3)0.047 (2)0.039 (2)−0.016 (2)0.019 (2)0.0006 (17)
C150.067 (3)0.044 (2)0.053 (2)−0.0125 (19)0.027 (2)0.0010 (18)
C160.084 (3)0.055 (3)0.065 (3)−0.007 (2)0.028 (3)0.005 (2)
C170.090 (4)0.059 (3)0.094 (4)−0.004 (3)0.044 (3)0.003 (3)
C180.069 (3)0.069 (3)0.088 (4)−0.004 (2)0.022 (3)0.009 (3)
C190.071 (3)0.069 (3)0.060 (3)−0.012 (2)0.013 (2)0.005 (2)
C200.064 (3)0.044 (2)0.053 (2)−0.0135 (19)0.020 (2)0.0092 (18)
C210.099 (5)0.161 (8)0.116 (5)−0.012 (4)−0.004 (4)0.020 (4)

Geometric parameters (Å, °)

Ni1—O11.835 (3)C9—C101.349 (8)
Ni1—O21.841 (3)C9—H90.9300
Ni1—N11.854 (3)C10—C111.391 (8)
Ni1—N21.866 (3)C10—H100.9300
Cl1—C41.729 (5)C11—C121.375 (7)
O1—C131.306 (5)C11—H110.9300
O2—C201.285 (5)C12—C131.425 (6)
N1—C71.302 (5)C12—H120.9300
N1—C11.422 (5)C14—C151.398 (6)
N2—C141.298 (5)C14—H140.9300
N2—C21.403 (5)C15—C161.400 (6)
C1—C61.386 (6)C15—C201.444 (6)
C1—C21.397 (6)C16—C171.372 (7)
C2—C31.390 (6)C16—H160.9300
C3—C41.363 (6)C17—C181.381 (7)
C3—H30.9300C17—H170.9300
C4—C51.395 (7)C18—C191.390 (7)
C5—C61.349 (6)C18—H180.9300
C5—C211.505 (8)C19—C201.390 (6)
C6—H60.9300C19—H190.9300
C7—C81.428 (6)C21—H21A0.9600
C7—H70.9300C21—H21B0.9600
C8—C131.402 (6)C21—H21C0.9600
C8—C91.417 (6)
O1—Ni1—O283.34 (13)C8—C9—H9119.3
O1—Ni1—N195.17 (14)C9—C10—C11119.3 (5)
O2—Ni1—N1178.50 (13)C9—C10—H10120.3
O1—Ni1—N2178.89 (14)C11—C10—H10120.3
O2—Ni1—N295.55 (14)C12—C11—C10121.3 (5)
N1—Ni1—N285.94 (14)C12—C11—H11119.4
C13—O1—Ni1127.3 (3)C10—C11—H11119.4
C20—O2—Ni1127.9 (3)C11—C12—C13120.5 (5)
C7—N1—C1120.3 (4)C11—C12—H12119.7
C7—N1—Ni1126.3 (3)C13—C12—H12119.7
C1—N1—Ni1113.4 (3)O1—C13—C8124.6 (4)
C14—N2—C2122.4 (3)O1—C13—C12117.9 (5)
C14—N2—Ni1124.4 (3)C8—C13—C12117.5 (4)
C2—N2—Ni1113.2 (3)N2—C14—C15127.2 (4)
C6—C1—C2119.2 (4)N2—C14—H14116.4
C6—C1—N1127.6 (4)C15—C14—H14116.4
C2—C1—N1113.2 (4)C14—C15—C16120.0 (4)
C3—C2—C1119.1 (4)C14—C15—C20121.0 (4)
C3—C2—N2126.6 (4)C16—C15—C20118.9 (4)
C1—C2—N2114.3 (3)C17—C16—C15121.8 (5)
C4—C3—C2119.8 (5)C17—C16—H16119.1
C4—C3—H3120.1C15—C16—H16119.1
C2—C3—H3120.1C16—C17—C18119.6 (5)
C3—C4—C5121.6 (4)C16—C17—H17120.2
C3—C4—Cl1120.7 (4)C18—C17—H17120.2
C5—C4—Cl1117.6 (4)C17—C18—C19120.2 (5)
C6—C5—C4118.3 (5)C17—C18—H18119.9
C6—C5—C21131.9 (6)C19—C18—H18119.9
C4—C5—C21109.4 (5)C18—C19—C20122.0 (5)
C5—C6—C1122.1 (5)C18—C19—H19119.0
C5—C6—H6119.0C20—C19—H19119.0
C1—C6—H6119.0O2—C20—C19119.0 (4)
N1—C7—C8124.8 (4)O2—C20—C15123.6 (4)
N1—C7—H7117.6C19—C20—C15117.4 (4)
C8—C7—H7117.6C5—C21—H21A109.5
C13—C8—C9119.9 (4)C5—C21—H21B109.5
C13—C8—C7121.6 (4)H21A—C21—H21B109.5
C9—C8—C7118.4 (5)C5—C21—H21C109.5
C10—C9—C8121.4 (6)H21A—C21—H21C109.5
C10—C9—H9119.3H21B—C21—H21C109.5

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV2792).

References

  • Ali, A., Abdullah, N., Maah, M. J. & Lo, K. M. (2010). Acta Cryst. E66, m458. [PMC free article] [PubMed]
  • Bruker (2001). SAINT-Plus Bruker AXS Inc., Madison, Wisconsin, USA.
  • Bruker (2004). APEX2 Bruker AXS Inc., Madison, Wisconsin, USA.
  • Hernandez-Molina, R., Mederos, A., Gili, P., Dominguez, S., Nunez, P., Germain, G. & Debaerdemaeker, T. (1997). Inorg. Chim. Acta, 256, 319–325.
  • Niu, M., Liu, G., Wang, D. & Dou, J. (2009). Acta Cryst. E65, m1357. [PMC free article] [PubMed]
  • Radha, A., Seshasayee, M., Ramalingam, K. & Aravamudan, G. (1985). Acta Cryst. C41, 1169–1171.
  • Sheldrick, G. M. (2007). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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