metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

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 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[Ali, A., Abdullah, N., Maah, M. J. & Lo, K. M. (2010). Acta Cryst. E66, m458.]); Hernandez-Molina et al. (1997[Hernandez-Molina, R., Mederos, A., Gili, P., Dominguez, S., Nunez, P., Germain, G. & Debaerdemaeker, T. (1997). Inorg. Chim. Acta, 256, 319-325.]); Niu et al. (2009[Niu, M., Liu, G., Wang, D. & Dou, J. (2009). Acta Cryst. E65, m1357.]); Radha et al. (1985[Radha, A., Seshasayee, M., Ramalingam, K. & Aravamudan, G. (1985). Acta Cryst. C41, 1169-1171.]).

[Scheme 1]

Experimental

Crystal data
  • [Ni(C21H15ClN2O2)]

  • Mr = 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[Sheldrick, G. M. (2007). SADABS. University of Göttingen, Germany.]) Tmin = 0.658, Tmax = 0.747

  • 7946 measured reflections

  • 2917 independent reflections

  • 2155 reflections with I > 2σ(I)

  • Rint = 0.040

Refinement
  • R[F2 > 2σ(F2)] = 0.052

  • wR(F2) = 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[Bruker (2004). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2001[Bruker (2001). SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


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 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).

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%.

Refinement top

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).

Structure description 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 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).

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
[Figure 1] 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
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 top
Bruker APEXII CCD area-detector
diffractometer
2917 independent reflections
Radiation source: fine-focus sealed tube2155 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.040
φ and ω scansθmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2007)
h = 1313
Tmin = 0.658, Tmax = 0.747k = 99
7946 measured reflectionsl = 2319
Refinement top
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 = 1.03 w = 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
Crystal data top
[Ni(C21H15ClN2O2)]V = 1665.5 (3) Å3
Mr = 421.51Z = 4
Monoclinic, P21/cMo Kα radiation
a = 11.0451 (10) ŵ = 1.35 mm1
b = 8.0202 (7) ÅT = 293 K
c = 19.5959 (17) Å0.34 × 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)
Tmin = 0.658, Tmax = 0.747Rint = 0.040
7946 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0520 restraints
wR(F2) = 0.153H-atom parameters constrained
S = 1.03Δρmax = 0.67 e Å3
2917 reflectionsΔρmin = 0.91 e Å3
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
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)
H30.34300.70890.19990.075*
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)
H60.09081.04490.10650.083*
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)
H140.49970.62280.12150.064*
C150.6325 (4)0.5970 (5)0.0291 (2)0.0529 (10)
C160.7113 (5)0.4956 (5)0.0562 (3)0.0669 (12)
H160.68550.46520.10390.080*
C170.8255 (5)0.4398 (6)0.0143 (3)0.0774 (14)
H170.87560.37140.03340.093*
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)
H21A0.07840.99560.24550.199*
H21B0.00050.95390.29890.199*
H21C0.01441.12830.26130.199*
Atomic displacement parameters (Å2) top
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, º) top
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

Experimental details

Crystal data
Chemical formula[Ni(C21H15ClN2O2)]
Mr421.51
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)11.0451 (10), 8.0202 (7), 19.5959 (17)
β (°) 106.37
V3)1665.5 (3)
Z4
Radiation typeMo Kα
µ (mm1)1.35
Crystal size (mm)0.34 × 0.29 × 0.23
Data collection
DiffractometerBruker APEXII CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2007)
Tmin, Tmax0.658, 0.747
No. of measured, independent and
observed [I > 2σ(I)] reflections
7946, 2917, 2155
Rint0.040
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.052, 0.153, 1.03
No. of reflections2917
No. of parameters245
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.67, 0.91

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

 

References

First citationAli, A., Abdullah, N., Maah, M. J. & Lo, K. M. (2010). Acta Cryst. E66, m458.  Web of Science CrossRef IUCr Journals Google Scholar
First citationBruker (2001). SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationBruker (2004). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationHernandez-Molina, R., Mederos, A., Gili, P., Dominguez, S., Nunez, P., Germain, G. & Debaerdemaeker, T. (1997). Inorg. Chim. Acta, 256, 319–325.  CSD CrossRef CAS Web of Science Google Scholar
First citationNiu, M., Liu, G., Wang, D. & Dou, J. (2009). Acta Cryst. E65, m1357.  Web of Science CrossRef IUCr Journals Google Scholar
First citationRadha, A., Seshasayee, M., Ramalingam, K. & Aravamudan, G. (1985). Acta Cryst. C41, 1169–1171.  CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationSheldrick, G. M. (2007). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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