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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

{2,2′-[(2,2-Di­methyl­propane-1,3-diyl­di­nitrilo)­bis­­(phenyl­methyl­­idyne)]­diphenolato}nickel(II)

aChemistry Department, Payame Noor University, Tehran 19395-4697, Iran, bX-ray Crystallography Laboratory, Plasma Physics Research Center, and Department of Chemistry, Science and Research Branch, Islamic Azad University, Tehran, Iran, cCatalysis Division, Department of Chemistry, University of Isfahan, Isfahan 81746-73441, Iran, and dDepartment of Physics, University of Sargodha, Punjab, Pakistan
*Correspondence e-mail: hkargar@pnu.ac.ir, dmntahir_uos@yahoo.com

(Received 16 July 2011; accepted 22 July 2011; online 2 August 2011)

The asymmetric unit of the title complex, [Ni(C31H28N2O2)], comprises two crystallographically independent mol­ecules. The geometry around the NiII atom in each mol­ecule is distorted square planar. The dihedral angles between the two phen­oxy rings in each mol­ecule are 17.8 (4) and 36.5 (4)°. The crystal packing is stabilized by weak ππ inter­actions [centroid–centroid distance = 3.758 (5) Å] and C—H⋯π inter­actions.

Related literature

For standard values of bond lengths, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]). For background on tetra­dentate Schiff bases and their complexes, see: Kargar et al. (2010[Kargar, H., Kia, R., Ullah Khan, I. & Sahraei, A. (2010). Acta Cryst. E66, o539.], 2009[Kargar, H., Kia, R., Jamshidvand, A. & Fun, H.-K. (2009). Acta Cryst. E65, o776-o777.]).

[Scheme 1]

Experimental

Crystal data
  • [Ni(C31H28N2O2)]

  • Mr = 519.26

  • Monoclinic, P 21 /c

  • a = 23.722 (3) Å

  • b = 9.4716 (6) Å

  • c = 26.961 (4) Å

  • β = 124.319 (9)°

  • V = 5003.2 (10) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.81 mm−1

  • T = 291 K

  • 0.24 × 0.12 × 0.08 mm

Data collection
  • Stoe IPDS 2T image-plate diffractometer

  • Absorption correction: multi-scan [MULABS (Blessing, 1995[Blessing, R. H. (1995). Acta Cryst. A51, 33-38.]) in PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.])] Tmin = 0.830, Tmax = 1.000

  • 23324 measured reflections

  • 8608 independent reflections

  • 2512 reflections with I > 2σ(I)

  • Rint = 0.117

Refinement
  • R[F2 > 2σ(F2)] = 0.053

  • wR(F2) = 0.097

  • S = 0.61

  • 8608 reflections

  • 649 parameters

  • H-atom parameters constrained

  • Δρmax = 0.23 e Å−3

  • Δρmin = −0.24 e Å−3

Table 1
Table 1[link]. C—H⋯π inter­actions (Å, °)

Cg2, Cg3 and Cg4 are the centroids of the C18–C23, C32–C37 and C55–C60 rings, respectively.

C—H⋯Cg C—H H⋯Cg C⋯Cg C—H⋯Cg
C21—H21ACg2ii 0.93 2.90 3.757 (11) 153
C41—H41ACg3iii 0.93 2.83 3.680 (12) 153
C44—H44ACg4iv 0.93 2.95 3.708 (10) 149
C47—H47ACg4v 0.93 2.92 3.884 (9) 171
Symmetry codes: (ii) x, [{3\over 2}] − y, [{1\over 2}] + z; (iii) 1 − x, 2 − y, 1 − z; (iv) 1 − x, −[{1\over 2}] + y, [{3\over 2}] − z; (v) 1 − x, [{1\over 2}] + y, [{3\over 2}] − z.

Data collection: X-AREA (Stoe & Cie, 2009[Stoe & Cie (2009). X-AREA and X-RED. Stoe & Cie, Darmstadt, Germany.]); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2009[Stoe & Cie (2009). X-AREA and X-RED. Stoe & Cie, Darmstadt, Germany.]); 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 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

Schiff base ligands are one of the most prevalent systems in coordination chemistry. As part of a general study of potentially tetradenate Schiff bases and their complexes (Kargar et al., 2009; Kargar et al., 2010), we have determined the crystal structure of the title compound.

The asymmetric unit of the title compound, Fig. 1, comprises two crystallographically independent molecules (A and B). The bond lengths in the complex are normal (Allen et al., 1987). The geometry around the NiII atoms in each molecule is distorted square planar. The dihedral angles between the coordination planes (O1—Ni1—N1 and O2—Ni1—N2 in molecule A and O3—Ni2—N3 and O4—Ni2—N4 in molecule B) are 13.43 (24) and 11.83 (32) Å, respectively. The dihedral angles between the two phenoxy rings (C1–C6) and (C24–C29) in molecule A, and (C32–C37) and (C55–C60) in molecule B, are 17.8 (4) and 36.5 (4)°, respectively.

The crystal packing is stabilized by weak ππ interactions [Cg1···Cg1i = 3.758 (5) Å, perpendiculaire separation 3.750 (4) Å, slippage 1.171 Å; (i) 2 - x, 2 - y, 1 - z; Cg1 is the centroid of benzene ring (C1-C6)]. There are also a number of C-H···π interactions present (Table 1).

Related literature top

For standard values of bond lengths, see: Allen et al. (1987). For background on tetradentate Schiff bases and their complexes, see: Kargar et al. (2010, 2009).

Experimental top

The title compound was synthesized by adding a methanolic solution (25 ml) of bis(2-hydroxybenzophenone)-2,2'-dimethyl propanediimine (2 mmol) to a solution of NiCl2.6H2O (2 mmol in 25 ml ethanol). The mixture was refluxed with stirring for 30 min. The resultant green solution was filtered. Dark-red single crystals, suitable for X-ray diffraction analysis, were obtained by recrystallization from ethanol by slow evaporation of the solvent at room temperature over several days.

Refinement top

The quality of the crystal was not optimal and it diffracted weakly; only 29% of the data can be considered to be observed [I>2σ(I)]. Although recrystallization was attempted repeatedly, better crystals could not be obtained. The C-bound H-atoms were included in calculated positions and treated as riding atoms: C-H = 0.93, 0.97 and 0.96 Å for CH, CH2 and CH3 H-atoms, respectively, with Uiso(H) = k × Ueq(parent C-atom), where k = 1.5 for CH3 H-atoms and k = 1.2 for all other H-atoms.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2009); cell refinement: X-AREA (Stoe & Cie, 2009); data reduction: X-RED (Stoe & Cie, 2009); 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) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the two independent molecules (A and B) of the title compound, showing 30% probability displacement ellipsoids and the atomic numbering [H-atoms have been removed for clarity].
{2,2'-[(2,2-Dimethylpropane-1,3- diyldinitrilo)bis(phenylmethylidyne)]diphenolato}nickel(II) top
Crystal data top
[Ni(C31H28N2O2)]F(000) = 2176
Mr = 519.26Dx = 1.379 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 220 reflections
a = 23.722 (3) Åθ = 2.9–20.0°
b = 9.4716 (6) ŵ = 0.81 mm1
c = 26.961 (4) ÅT = 291 K
β = 124.319 (9)°Block, dark-red
V = 5003.2 (10) Å30.24 × 0.12 × 0.08 mm
Z = 8
Data collection top
Stoe IPDS 2T image-plate
diffractometer
8608 independent reflections
Radiation source: fine-focus sealed tube2512 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.117
ω scansθmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan
[MULABS (Blessing, 1995) in PLATON (Spek, 2009)]
h = 2827
Tmin = 0.830, Tmax = 1.000k = 1011
23324 measured reflectionsl = 3032
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)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097H-atom parameters constrained
S = 0.61 w = 1/[σ2(Fo2) + (0.005P)2]
where P = (Fo2 + 2Fc2)/3
8608 reflections(Δ/σ)max = 0.001
649 parametersΔρmax = 0.23 e Å3
0 restraintsΔρmin = 0.24 e Å3
Crystal data top
[Ni(C31H28N2O2)]V = 5003.2 (10) Å3
Mr = 519.26Z = 8
Monoclinic, P21/cMo Kα radiation
a = 23.722 (3) ŵ = 0.81 mm1
b = 9.4716 (6) ÅT = 291 K
c = 26.961 (4) Å0.24 × 0.12 × 0.08 mm
β = 124.319 (9)°
Data collection top
Stoe IPDS 2T image-plate
diffractometer
8608 independent reflections
Absorption correction: multi-scan
[MULABS (Blessing, 1995) in PLATON (Spek, 2009)]
2512 reflections with I > 2σ(I)
Tmin = 0.830, Tmax = 1.000Rint = 0.117
23324 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0530 restraints
wR(F2) = 0.097H-atom parameters constrained
S = 0.61Δρmax = 0.23 e Å3
8608 reflectionsΔρmin = 0.24 e Å3
649 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
Ni11.02997 (5)0.78653 (13)0.65990 (4)0.0311 (3)
O11.0842 (2)0.8006 (7)0.6312 (2)0.0507 (19)
O21.1123 (2)0.8077 (7)0.7328 (2)0.054 (2)
N10.9521 (3)0.7266 (8)0.5836 (2)0.0324 (19)
N20.9807 (3)0.8051 (7)0.6956 (2)0.0290 (18)
C11.0658 (4)0.8149 (10)0.5766 (3)0.034 (2)
C21.1152 (4)0.8582 (9)0.5660 (3)0.038 (3)
H2A1.15950.87550.59890.046*
C31.1012 (4)0.8759 (10)0.5096 (3)0.044 (3)
H3A1.13520.90400.50460.052*
C41.0358 (4)0.8513 (10)0.4605 (3)0.047 (3)
H4A1.02530.86360.42200.057*
C50.9863 (4)0.8089 (10)0.4683 (3)0.043 (3)
H5A0.94240.79340.43460.052*
C60.9993 (3)0.7877 (9)0.5257 (3)0.031 (2)
C70.9468 (3)0.7330 (9)0.5322 (3)0.033 (2)
C80.8828 (4)0.6750 (10)0.4753 (3)0.030 (2)
C90.8779 (4)0.5353 (10)0.4586 (3)0.044 (3)
H9A0.91470.47450.48130.053*
C100.8181 (4)0.4868 (10)0.4081 (3)0.050 (3)
H10A0.81470.39230.39740.061*
C110.7642 (4)0.5735 (11)0.3738 (3)0.048 (3)
H11A0.72360.53780.34090.057*
C120.7699 (4)0.7168 (11)0.3879 (3)0.046 (3)
H12A0.73410.77780.36280.055*
C130.8287 (4)0.7687 (10)0.4393 (3)0.046 (3)
H13A0.83230.86350.44970.055*
C140.9025 (3)0.6505 (8)0.5891 (3)0.033 (2)
H14A0.92620.57740.61920.040*
H14B0.87040.60410.55110.040*
C150.8626 (4)0.7401 (9)0.6057 (3)0.034 (2)
C160.9092 (3)0.8557 (9)0.6521 (3)0.036 (2)
H16A0.91000.93740.63080.044*
H16B0.89000.88510.67410.044*
C171.0024 (4)0.7955 (9)0.7519 (3)0.028 (2)
C180.9564 (4)0.8038 (10)0.7730 (3)0.030 (2)
C190.9331 (4)0.6818 (10)0.7838 (3)0.040 (2)
H19A0.94540.59460.77680.048*
C200.8916 (3)0.6868 (11)0.8048 (3)0.042 (3)
H20A0.87590.60380.81160.051*
C210.8737 (4)0.8168 (14)0.8157 (4)0.056 (3)
H21A0.84640.82160.83040.068*
C220.8962 (4)0.9379 (11)0.8048 (4)0.051 (3)
H22A0.88331.02490.81130.061*
C230.9380 (4)0.9330 (10)0.7842 (3)0.038 (3)
H23A0.95381.01630.77780.046*
C241.0757 (3)0.7739 (9)0.7995 (3)0.032 (2)
C251.0976 (4)0.7541 (9)0.8595 (3)0.042 (3)
H25A1.06500.75070.86840.051*
C261.1646 (4)0.7396 (10)0.9052 (3)0.054 (3)
H26A1.17770.72510.94440.065*
C271.2131 (4)0.7473 (11)0.8914 (3)0.056 (3)
H27A1.25920.73800.92190.067*
C281.1944 (4)0.7678 (10)0.8345 (3)0.054 (3)
H28A1.22800.77180.82690.065*
C291.1253 (4)0.7834 (10)0.7860 (3)0.035 (2)
C300.8047 (3)0.8248 (9)0.5513 (3)0.055 (3)
H30A0.77360.76050.52010.083*
H30B0.82400.88660.53630.083*
H30C0.78070.87970.56370.083*
C310.8321 (4)0.6435 (10)0.6292 (3)0.059 (3)
H31A0.86790.59180.66310.088*
H31B0.80130.57860.59820.088*
H31C0.80770.69860.64110.088*
Ni20.53222 (5)0.89266 (12)0.72050 (4)0.0273 (3)
O30.6131 (2)0.9183 (7)0.7276 (2)0.0426 (18)
O40.5829 (2)0.9419 (7)0.8019 (2)0.0405 (18)
N30.4869 (3)0.8180 (7)0.6412 (2)0.0281 (18)
N40.4505 (3)0.9045 (7)0.7181 (2)0.0285 (18)
C320.6266 (4)0.9007 (10)0.6874 (3)0.032 (2)
C330.6938 (4)0.9313 (9)0.7043 (3)0.038 (2)
H33A0.72550.96470.74290.046*
C340.7135 (4)0.9136 (10)0.6662 (3)0.045 (3)
H34A0.75760.93710.67820.054*
C350.6674 (4)0.8602 (9)0.6091 (3)0.046 (3)
H35A0.68110.84390.58330.056*
C360.6019 (4)0.8316 (9)0.5906 (3)0.037 (3)
H36A0.57140.79940.55160.044*
C370.5787 (3)0.8485 (9)0.6275 (3)0.028 (2)
C380.5097 (3)0.8071 (9)0.6077 (3)0.025 (2)
C390.4662 (4)0.7477 (10)0.5448 (3)0.034 (2)
C400.4368 (4)0.8401 (10)0.4967 (3)0.043 (3)
H40A0.44250.93700.50330.051*
C410.3986 (4)0.7873 (13)0.4380 (3)0.053 (3)
H41A0.38000.84830.40530.063*
C420.3889 (4)0.6428 (13)0.4292 (4)0.054 (3)
H42A0.36180.60700.39040.065*
C430.4190 (4)0.5516 (11)0.4773 (4)0.054 (3)
H43A0.41350.45470.47100.065*
C440.4577 (4)0.6055 (10)0.5355 (3)0.043 (2)
H44A0.47780.54430.56810.051*
C450.4199 (3)0.7514 (8)0.6211 (3)0.029 (2)
H45A0.42720.68510.65160.035*
H45B0.40360.69830.58460.035*
C460.3645 (3)0.8560 (9)0.6092 (3)0.033 (2)
C470.3940 (3)0.9652 (9)0.6615 (3)0.036 (2)
H47A0.40991.04800.65170.043*
H47B0.35810.99470.66630.043*
C480.4448 (3)0.8768 (9)0.7615 (3)0.026 (2)
C490.3789 (3)0.8908 (11)0.7567 (3)0.029 (2)
C500.3352 (4)0.7777 (11)0.7428 (3)0.044 (3)
H50A0.34670.68800.73720.053*
C510.2742 (4)0.8000 (12)0.7373 (3)0.056 (3)
H51A0.24450.72480.72780.067*
C520.2570 (4)0.9323 (12)0.7456 (4)0.058 (3)
H52A0.21540.94620.74090.070*
C530.2999 (4)1.0415 (11)0.7606 (4)0.055 (3)
H53A0.28821.12980.76730.066*
C540.3611 (4)1.0242 (10)0.7661 (4)0.044 (3)
H54A0.39031.10060.77600.052*
C550.5051 (4)0.8366 (9)0.8212 (3)0.031 (2)
C560.4964 (3)0.7722 (10)0.8633 (3)0.041 (3)
H56A0.45320.74190.85160.049*
C570.5511 (4)0.7536 (10)0.9217 (3)0.051 (3)
H57A0.54530.70760.94910.061*
C580.6140 (4)0.8031 (11)0.9394 (3)0.052 (3)
H58A0.65030.79360.97940.063*
C590.6246 (4)0.8659 (10)0.8999 (3)0.050 (3)
H59A0.66790.89880.91340.060*
C600.5695 (4)0.8823 (10)0.8375 (3)0.029 (2)
C610.3381 (4)0.9449 (10)0.5511 (3)0.059 (3)
H61A0.31970.88270.51720.088*
H61B0.37520.99800.55560.088*
H61C0.30311.00840.54480.088*
C620.3060 (3)0.7700 (10)0.6021 (4)0.058 (3)
H62A0.32230.71700.63810.087*
H62B0.28860.70630.56880.087*
H62C0.27020.83250.59480.087*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.0228 (5)0.0430 (8)0.0227 (5)0.0028 (6)0.0098 (4)0.0008 (6)
O10.026 (3)0.097 (6)0.028 (3)0.009 (3)0.015 (3)0.001 (3)
O20.022 (3)0.103 (6)0.029 (3)0.010 (3)0.010 (3)0.001 (3)
N10.030 (4)0.043 (6)0.027 (3)0.005 (4)0.019 (3)0.001 (4)
N20.021 (3)0.037 (5)0.028 (3)0.000 (3)0.013 (3)0.000 (3)
C10.039 (5)0.038 (7)0.037 (5)0.003 (5)0.028 (4)0.003 (4)
C20.028 (4)0.053 (8)0.037 (4)0.007 (4)0.020 (4)0.000 (4)
C30.042 (5)0.059 (8)0.037 (5)0.006 (5)0.027 (4)0.007 (5)
C40.048 (5)0.071 (9)0.036 (5)0.000 (5)0.031 (5)0.001 (5)
C50.032 (4)0.062 (8)0.026 (4)0.009 (5)0.010 (4)0.004 (5)
C60.022 (4)0.043 (6)0.030 (4)0.009 (4)0.017 (4)0.001 (4)
C70.026 (4)0.032 (6)0.025 (4)0.006 (4)0.005 (4)0.001 (4)
C80.028 (4)0.035 (7)0.024 (4)0.004 (4)0.014 (4)0.005 (4)
C90.033 (5)0.047 (7)0.042 (5)0.007 (5)0.016 (4)0.002 (5)
C100.048 (6)0.045 (7)0.039 (5)0.002 (5)0.013 (5)0.011 (5)
C110.029 (5)0.074 (9)0.029 (4)0.026 (5)0.009 (4)0.020 (5)
C120.031 (4)0.072 (8)0.030 (4)0.011 (5)0.014 (4)0.007 (5)
C130.051 (5)0.052 (7)0.032 (4)0.000 (5)0.022 (4)0.007 (5)
C140.022 (4)0.043 (7)0.027 (4)0.005 (4)0.009 (4)0.003 (4)
C150.031 (4)0.039 (7)0.026 (4)0.002 (4)0.012 (4)0.010 (4)
C160.030 (4)0.044 (7)0.034 (4)0.015 (4)0.018 (4)0.015 (4)
C170.035 (4)0.030 (6)0.026 (4)0.003 (5)0.022 (4)0.004 (4)
C180.028 (4)0.035 (6)0.027 (4)0.005 (5)0.016 (4)0.003 (5)
C190.036 (5)0.036 (7)0.044 (5)0.004 (4)0.020 (4)0.010 (5)
C200.027 (4)0.078 (9)0.032 (4)0.012 (5)0.023 (4)0.004 (5)
C210.036 (5)0.106 (11)0.041 (5)0.014 (6)0.030 (4)0.000 (6)
C220.041 (5)0.053 (9)0.057 (6)0.006 (5)0.026 (5)0.001 (6)
C230.038 (5)0.049 (8)0.039 (5)0.009 (5)0.029 (4)0.006 (5)
C240.016 (4)0.046 (7)0.026 (4)0.002 (4)0.006 (3)0.006 (4)
C250.039 (5)0.049 (8)0.043 (5)0.003 (5)0.026 (4)0.013 (5)
C260.038 (5)0.093 (10)0.017 (4)0.002 (5)0.006 (4)0.019 (5)
C270.028 (4)0.100 (10)0.031 (4)0.010 (5)0.012 (4)0.029 (5)
C280.029 (4)0.093 (9)0.041 (5)0.000 (5)0.020 (4)0.012 (6)
C290.025 (4)0.045 (7)0.029 (4)0.007 (4)0.011 (4)0.001 (5)
C300.034 (5)0.081 (9)0.039 (4)0.011 (5)0.014 (4)0.010 (5)
C310.052 (5)0.079 (9)0.056 (5)0.023 (5)0.037 (5)0.014 (5)
Ni20.0227 (5)0.0371 (8)0.0204 (5)0.0030 (6)0.0112 (4)0.0031 (6)
O30.029 (3)0.065 (5)0.032 (3)0.003 (3)0.016 (3)0.002 (3)
O40.030 (3)0.066 (5)0.029 (3)0.016 (3)0.018 (3)0.012 (3)
N30.023 (3)0.026 (5)0.035 (3)0.001 (3)0.016 (3)0.002 (3)
N40.024 (3)0.034 (5)0.021 (3)0.001 (3)0.009 (3)0.004 (4)
C320.025 (4)0.037 (6)0.037 (5)0.001 (4)0.019 (4)0.002 (5)
C330.032 (5)0.042 (7)0.032 (4)0.008 (4)0.013 (4)0.004 (4)
C340.039 (5)0.066 (8)0.042 (5)0.005 (5)0.031 (4)0.008 (5)
C350.051 (5)0.066 (8)0.048 (5)0.002 (5)0.044 (5)0.016 (5)
C360.031 (5)0.053 (8)0.021 (4)0.009 (4)0.012 (4)0.006 (4)
C370.018 (4)0.039 (7)0.028 (4)0.001 (4)0.014 (4)0.002 (4)
C380.033 (4)0.017 (6)0.032 (4)0.006 (4)0.022 (4)0.010 (4)
C390.031 (4)0.044 (7)0.026 (4)0.005 (4)0.015 (4)0.007 (4)
C400.039 (5)0.051 (8)0.033 (5)0.015 (5)0.017 (4)0.005 (5)
C410.042 (5)0.089 (9)0.025 (4)0.011 (6)0.017 (4)0.000 (6)
C420.049 (6)0.088 (10)0.019 (4)0.011 (6)0.015 (4)0.028 (6)
C430.063 (6)0.051 (8)0.051 (6)0.003 (6)0.034 (5)0.012 (6)
C440.045 (5)0.034 (7)0.042 (5)0.002 (5)0.021 (4)0.006 (5)
C450.031 (4)0.027 (6)0.025 (4)0.014 (4)0.013 (3)0.005 (4)
C460.022 (4)0.042 (7)0.029 (4)0.003 (4)0.010 (4)0.003 (4)
C470.026 (4)0.047 (7)0.034 (4)0.005 (4)0.017 (4)0.016 (4)
C480.022 (4)0.021 (6)0.032 (4)0.005 (4)0.015 (4)0.007 (4)
C490.018 (4)0.041 (6)0.026 (4)0.018 (5)0.012 (3)0.015 (5)
C500.039 (5)0.050 (7)0.046 (5)0.003 (5)0.025 (4)0.005 (5)
C510.027 (5)0.081 (9)0.054 (5)0.001 (6)0.021 (4)0.029 (6)
C520.031 (5)0.079 (10)0.072 (7)0.022 (6)0.033 (5)0.027 (7)
C530.048 (6)0.041 (8)0.073 (6)0.012 (5)0.033 (5)0.001 (6)
C540.041 (5)0.038 (7)0.060 (6)0.006 (5)0.033 (5)0.003 (5)
C550.034 (5)0.043 (7)0.023 (4)0.004 (4)0.020 (4)0.005 (4)
C560.025 (4)0.065 (8)0.036 (4)0.010 (5)0.019 (4)0.005 (5)
C570.056 (6)0.065 (9)0.041 (5)0.021 (6)0.032 (5)0.017 (5)
C580.043 (5)0.080 (9)0.034 (5)0.019 (6)0.022 (4)0.012 (6)
C590.025 (4)0.082 (9)0.043 (5)0.008 (5)0.020 (4)0.008 (5)
C600.028 (5)0.034 (6)0.032 (4)0.005 (4)0.020 (4)0.001 (4)
C610.055 (6)0.066 (8)0.041 (5)0.009 (5)0.019 (5)0.007 (5)
C620.036 (5)0.070 (9)0.074 (6)0.012 (5)0.035 (5)0.015 (6)
Geometric parameters (Å, º) top
Ni1—O21.841 (4)Ni2—O31.833 (5)
Ni1—O11.841 (5)Ni2—O41.872 (5)
Ni1—N21.896 (6)Ni2—N41.904 (6)
Ni1—N11.918 (5)Ni2—N31.907 (6)
O1—C11.286 (8)O3—C321.304 (9)
O2—C291.307 (9)O4—C601.298 (9)
N1—C71.319 (9)N3—C381.292 (9)
N1—C141.458 (9)N3—C451.498 (8)
N2—C171.302 (8)N4—C481.281 (9)
N2—C161.497 (8)N4—C471.466 (8)
C1—C61.413 (9)C32—C331.419 (10)
C1—C21.415 (11)C32—C371.441 (9)
C2—C31.369 (9)C33—C341.358 (10)
C2—H2A0.9300C33—H33A0.9300
C3—C41.378 (9)C34—C351.387 (9)
C3—H3A0.9300C34—H34A0.9300
C4—C51.363 (11)C35—C361.365 (10)
C4—H4A0.9300C35—H35A0.9300
C5—C61.410 (10)C36—C371.391 (10)
C5—H5A0.9300C36—H36A0.9300
C6—C71.449 (10)C37—C381.460 (9)
C7—C81.528 (9)C38—C391.511 (9)
C8—C91.381 (10)C39—C441.364 (11)
C8—C131.403 (10)C39—C401.384 (10)
C9—C101.377 (10)C40—C411.400 (10)
C9—H9A0.9300C40—H40A0.9300
C10—C111.354 (10)C41—C421.386 (12)
C10—H10A0.9300C41—H41A0.9300
C11—C121.395 (12)C42—C431.375 (12)
C11—H11A0.9300C42—H42A0.9300
C12—C131.390 (9)C43—C441.393 (10)
C12—H12A0.9300C43—H43A0.9300
C13—H13A0.9300C44—H44A0.9300
C14—C151.514 (10)C45—C461.528 (10)
C14—H14A0.9700C45—H45A0.9700
C14—H14B0.9700C45—H45B0.9700
C15—C311.510 (10)C46—C621.527 (10)
C15—C301.553 (9)C46—C471.562 (10)
C15—C161.557 (10)C46—C611.564 (10)
C16—H16A0.9700C47—H47A0.9700
C16—H16B0.9700C47—H47B0.9700
C17—C241.481 (9)C48—C551.477 (9)
C17—C181.490 (11)C48—C491.500 (10)
C18—C191.381 (11)C49—C501.387 (11)
C18—C231.388 (11)C49—C541.399 (11)
C19—C201.386 (10)C50—C511.385 (11)
C19—H19A0.9300C50—H50A0.9300
C20—C211.388 (12)C51—C521.374 (12)
C20—H20A0.9300C51—H51A0.9300
C21—C221.366 (12)C52—C531.343 (12)
C21—H21A0.9300C52—H52A0.9300
C22—C231.384 (11)C53—C541.385 (11)
C22—H22A0.9300C53—H53A0.9300
C23—H23A0.9300C54—H54A0.9300
C24—C251.405 (9)C55—C601.400 (10)
C24—C291.415 (11)C55—C561.403 (10)
C25—C261.361 (9)C56—C571.375 (8)
C25—H25A0.9300C56—H56A0.9300
C26—C271.398 (11)C57—C581.367 (11)
C26—H26A0.9300C57—H57A0.9300
C27—C281.347 (10)C58—C591.362 (11)
C27—H27A0.9300C58—H58A0.9300
C28—C291.415 (9)C59—C601.444 (9)
C28—H28A0.9300C59—H59A0.9300
C30—H30A0.9600C61—H61A0.9600
C30—H30B0.9600C61—H61B0.9600
C30—H30C0.9600C61—H61C0.9600
C31—H31A0.9600C62—H62A0.9600
C31—H31B0.9600C62—H62B0.9600
C31—H31C0.9600C62—H62C0.9600
O2—Ni1—O182.5 (2)O3—Ni2—O484.3 (2)
O2—Ni1—N292.0 (2)O3—Ni2—N4168.5 (3)
O1—Ni1—N2169.5 (3)O4—Ni2—N489.7 (2)
O2—Ni1—N1167.8 (3)O3—Ni2—N393.6 (3)
O1—Ni1—N192.8 (2)O4—Ni2—N3172.1 (3)
N2—Ni1—N194.3 (2)N4—Ni2—N393.6 (2)
C1—O1—Ni1128.5 (5)C32—O3—Ni2129.0 (5)
C29—O2—Ni1127.2 (5)C60—O4—Ni2119.7 (5)
C7—N1—C14121.6 (6)C38—N3—C45119.4 (6)
C7—N1—Ni1125.2 (5)C38—N3—Ni2128.2 (5)
C14—N1—Ni1112.5 (5)C45—N3—Ni2112.0 (5)
C17—N2—C16117.8 (6)C48—N4—C47121.6 (6)
C17—N2—Ni1129.3 (5)C48—N4—Ni2126.0 (5)
C16—N2—Ni1112.4 (4)C47—N4—Ni2112.1 (5)
O1—C1—C6124.4 (8)O3—C32—C33117.8 (7)
O1—C1—C2118.5 (7)O3—C32—C37124.6 (7)
C6—C1—C2117.1 (7)C33—C32—C37117.6 (8)
C3—C2—C1123.2 (7)C34—C33—C32122.4 (7)
C3—C2—H2A118.4C34—C33—H33A118.8
C1—C2—H2A118.4C32—C33—H33A118.8
C2—C3—C4118.9 (8)C33—C34—C35119.4 (7)
C2—C3—H3A120.6C33—C34—H34A120.3
C4—C3—H3A120.6C35—C34—H34A120.3
C5—C4—C3120.2 (7)C36—C35—C34120.1 (7)
C5—C4—H4A119.9C36—C35—H35A119.9
C3—C4—H4A119.9C34—C35—H35A119.9
C4—C5—C6122.4 (7)C35—C36—C37122.9 (7)
C4—C5—H5A118.8C35—C36—H36A118.5
C6—C5—H5A118.8C37—C36—H36A118.5
C5—C6—C1118.2 (7)C36—C37—C32117.5 (6)
C5—C6—C7120.9 (6)C36—C37—C38121.4 (6)
C1—C6—C7120.8 (6)C32—C37—C38121.0 (7)
N1—C7—C6124.3 (6)N3—C38—C37123.3 (7)
N1—C7—C8119.4 (7)N3—C38—C39121.5 (6)
C6—C7—C8116.2 (6)C37—C38—C39115.2 (7)
C9—C8—C13120.3 (7)C44—C39—C40120.4 (7)
C9—C8—C7121.7 (7)C44—C39—C38120.8 (7)
C13—C8—C7118.0 (8)C40—C39—C38118.7 (8)
C10—C9—C8119.5 (8)C39—C40—C41119.8 (9)
C10—C9—H9A120.3C39—C40—H40A120.1
C8—C9—H9A120.3C41—C40—H40A120.1
C11—C10—C9121.5 (9)C42—C41—C40119.0 (9)
C11—C10—H10A119.2C42—C41—H41A120.5
C9—C10—H10A119.2C40—C41—H41A120.5
C10—C11—C12119.7 (7)C43—C42—C41120.8 (8)
C10—C11—H11A120.2C43—C42—H42A119.6
C12—C11—H11A120.2C41—C42—H42A119.6
C13—C12—C11120.3 (8)C42—C43—C44119.6 (10)
C13—C12—H12A119.9C42—C43—H43A120.2
C11—C12—H12A119.9C44—C43—H43A120.2
C12—C13—C8118.6 (9)C39—C44—C43120.4 (9)
C12—C13—H13A120.7C39—C44—H44A119.8
C8—C13—H13A120.7C43—C44—H44A119.8
N1—C14—C15115.3 (7)N3—C45—C46114.5 (6)
N1—C14—H14A108.5N3—C45—H45A108.6
C15—C14—H14A108.5C46—C45—H45A108.6
N1—C14—H14B108.5N3—C45—H45B108.6
C15—C14—H14B108.5C46—C45—H45B108.6
H14A—C14—H14B107.5H45A—C45—H45B107.6
C31—C15—C14108.1 (7)C62—C46—C45107.1 (6)
C31—C15—C30109.3 (6)C62—C46—C47112.2 (7)
C14—C15—C30112.2 (6)C45—C46—C47110.2 (5)
C31—C15—C16112.4 (6)C62—C46—C61109.8 (6)
C14—C15—C16110.7 (6)C45—C46—C61111.8 (7)
C30—C15—C16104.2 (7)C47—C46—C61105.8 (7)
N2—C16—C15112.4 (6)N4—C47—C46111.2 (6)
N2—C16—H16A109.1N4—C47—H47A109.4
C15—C16—H16A109.1C46—C47—H47A109.4
N2—C16—H16B109.1N4—C47—H47B109.4
C15—C16—H16B109.1C46—C47—H47B109.4
H16A—C16—H16B107.9H47A—C47—H47B108.0
N2—C17—C24121.3 (7)N4—C48—C55120.8 (6)
N2—C17—C18123.2 (6)N4—C48—C49123.1 (6)
C24—C17—C18115.6 (6)C55—C48—C49116.0 (7)
C19—C18—C23118.7 (8)C50—C49—C54119.5 (7)
C19—C18—C17120.2 (9)C50—C49—C48122.6 (9)
C23—C18—C17121.1 (9)C54—C49—C48118.0 (8)
C18—C19—C20121.3 (9)C51—C50—C49119.1 (9)
C18—C19—H19A119.4C51—C50—H50A120.4
C20—C19—H19A119.4C49—C50—H50A120.4
C19—C20—C21119.3 (9)C52—C51—C50120.6 (10)
C19—C20—H20A120.3C52—C51—H51A119.7
C21—C20—H20A120.3C50—C51—H51A119.7
C22—C21—C20119.7 (9)C53—C52—C51120.5 (9)
C22—C21—H21A120.2C53—C52—H52A119.7
C20—C21—H21A120.2C51—C52—H52A119.7
C21—C22—C23121.0 (10)C52—C53—C54120.8 (10)
C21—C22—H22A119.5C52—C53—H53A119.6
C23—C22—H22A119.5C54—C53—H53A119.6
C22—C23—C18120.0 (10)C53—C54—C49119.4 (9)
C22—C23—H23A120.0C53—C54—H54A120.3
C18—C23—H23A120.0C49—C54—H54A120.3
C25—C24—C29118.9 (6)C60—C55—C56120.9 (7)
C25—C24—C17120.5 (7)C60—C55—C48118.5 (7)
C29—C24—C17120.5 (6)C56—C55—C48120.0 (7)
C26—C25—C24122.7 (8)C57—C56—C55120.5 (7)
C26—C25—H25A118.7C57—C56—H56A119.7
C24—C25—H25A118.7C55—C56—H56A119.7
C25—C26—C27118.1 (7)C58—C57—C56119.7 (9)
C25—C26—H26A121.0C58—C57—H57A120.1
C27—C26—H26A121.0C56—C57—H57A120.1
C28—C27—C26121.2 (7)C59—C58—C57121.6 (7)
C28—C27—H27A119.4C59—C58—H58A119.2
C26—C27—H27A119.4C57—C58—H58A119.2
C27—C28—C29122.2 (8)C58—C59—C60120.9 (8)
C27—C28—H28A118.9C58—C59—H59A119.6
C29—C28—H28A118.9C60—C59—H59A119.6
O2—C29—C28117.7 (7)O4—C60—C55125.5 (6)
O2—C29—C24125.3 (6)O4—C60—C59118.1 (7)
C28—C29—C24117.0 (7)C55—C60—C59116.3 (8)
C15—C30—H30A109.5C46—C61—H61A109.5
C15—C30—H30B109.5C46—C61—H61B109.5
H30A—C30—H30B109.5H61A—C61—H61B109.5
C15—C30—H30C109.5C46—C61—H61C109.5
H30A—C30—H30C109.5H61A—C61—H61C109.5
H30B—C30—H30C109.5H61B—C61—H61C109.5
C15—C31—H31A109.5C46—C62—H62A109.5
C15—C31—H31B109.5C46—C62—H62B109.5
H31A—C31—H31B109.5H62A—C62—H62B109.5
C15—C31—H31C109.5C46—C62—H62C109.5
H31A—C31—H31C109.5H62A—C62—H62C109.5
H31B—C31—H31C109.5H62B—C62—H62C109.5
O2—Ni1—O1—C1169.8 (8)C17—C24—C29—C28177.2 (8)
N2—Ni1—O1—C1111.3 (13)O4—Ni2—O3—C32177.9 (8)
N1—Ni1—O1—C121.5 (8)N4—Ni2—O3—C32123.1 (13)
O1—Ni1—O2—C29165.6 (8)N3—Ni2—O3—C325.5 (8)
N2—Ni1—O2—C2923.3 (8)O3—Ni2—O4—C60144.8 (6)
N1—Ni1—O2—C2997.8 (15)N4—Ni2—O4—C6045.0 (6)
O2—Ni1—N1—C779.4 (17)O3—Ni2—N3—C385.1 (8)
O1—Ni1—N1—C712.6 (8)N4—Ni2—N3—C38165.9 (7)
N2—Ni1—N1—C7159.7 (8)O3—Ni2—N3—C45167.7 (5)
O2—Ni1—N1—C1491.0 (14)N4—Ni2—N3—C4521.3 (5)
O1—Ni1—N1—C14157.9 (6)O3—Ni2—N4—C4890.3 (15)
N2—Ni1—N1—C1429.9 (6)O4—Ni2—N4—C4831.7 (8)
O2—Ni1—N2—C1716.1 (8)N3—Ni2—N4—C48141.1 (8)
O1—Ni1—N2—C1773.8 (17)O3—Ni2—N4—C4783.4 (13)
N1—Ni1—N2—C17153.5 (8)O4—Ni2—N4—C47142.0 (5)
O2—Ni1—N2—C16155.5 (5)N3—Ni2—N4—C4745.2 (6)
O1—Ni1—N2—C1697.7 (13)Ni2—O3—C32—C33178.6 (6)
N1—Ni1—N2—C1635.0 (6)Ni2—O3—C32—C373.3 (14)
Ni1—O1—C1—C616.7 (14)O3—C32—C33—C34178.6 (9)
Ni1—O1—C1—C2164.6 (6)C37—C32—C33—C340.3 (14)
O1—C1—C2—C3179.6 (9)C32—C33—C34—C351.8 (15)
C6—C1—C2—C30.8 (14)C33—C34—C35—C362.8 (15)
C1—C2—C3—C40.3 (15)C34—C35—C36—C372.5 (15)
C2—C3—C4—C50.6 (14)C35—C36—C37—C321.0 (14)
C3—C4—C5—C60.4 (15)C35—C36—C37—C38175.4 (8)
C4—C5—C6—C11.5 (15)O3—C32—C37—C36178.0 (9)
C4—C5—C6—C7175.6 (9)C33—C32—C37—C360.1 (12)
O1—C1—C6—C5179.6 (9)O3—C32—C37—C381.6 (14)
C2—C1—C6—C51.7 (13)C33—C32—C37—C38176.6 (8)
O1—C1—C6—C73.3 (14)C45—N3—C38—C37170.0 (7)
C2—C1—C6—C7175.4 (8)Ni2—N3—C38—C372.3 (12)
C14—N1—C7—C6170.1 (7)C45—N3—C38—C399.1 (12)
Ni1—N1—C7—C60.5 (12)Ni2—N3—C38—C39178.6 (5)
C14—N1—C7—C87.6 (12)C36—C37—C38—N3178.3 (8)
Ni1—N1—C7—C8177.2 (6)C32—C37—C38—N32.0 (13)
C5—C6—C7—N1171.3 (9)C36—C37—C38—C390.9 (12)
C1—C6—C7—N111.7 (13)C32—C37—C38—C39177.1 (8)
C5—C6—C7—C811.0 (12)N3—C38—C39—C4479.4 (11)
C1—C6—C7—C8166.0 (8)C37—C38—C39—C4499.8 (9)
N1—C7—C8—C988.6 (11)N3—C38—C39—C40102.9 (10)
C6—C7—C8—C989.3 (10)C37—C38—C39—C4078.0 (10)
N1—C7—C8—C1392.5 (10)C44—C39—C40—C410.5 (13)
C6—C7—C8—C1389.6 (9)C38—C39—C40—C41177.3 (7)
C13—C8—C9—C103.6 (14)C39—C40—C41—C422.2 (13)
C7—C8—C9—C10177.5 (7)C40—C41—C42—C433.1 (15)
C8—C9—C10—C111.1 (14)C41—C42—C43—C442.2 (15)
C9—C10—C11—C123.0 (14)C40—C39—C44—C430.5 (14)
C10—C11—C12—C134.5 (14)C38—C39—C44—C43178.2 (8)
C11—C12—C13—C82.1 (12)C42—C43—C44—C390.4 (14)
C9—C8—C13—C122.0 (12)C38—N3—C45—C46116.3 (8)
C7—C8—C13—C12179.1 (7)Ni2—N3—C45—C4670.2 (7)
C7—N1—C14—C15117.5 (8)N3—C45—C46—C62168.5 (6)
Ni1—N1—C14—C1571.7 (7)N3—C45—C46—C4746.1 (8)
N1—C14—C15—C31161.6 (6)N3—C45—C46—C6171.2 (8)
N1—C14—C15—C3077.8 (8)C48—N4—C47—C46110.5 (9)
N1—C14—C15—C1638.1 (8)Ni2—N4—C47—C4675.5 (7)
C17—N2—C16—C15114.9 (8)C62—C46—C47—N491.3 (8)
Ni1—N2—C16—C1572.5 (7)C45—C46—C47—N428.0 (9)
C31—C15—C16—N285.4 (8)C61—C46—C47—N4149.0 (7)
C14—C15—C16—N235.6 (8)C47—N4—C48—C55170.5 (7)
C30—C15—C16—N2156.4 (6)Ni2—N4—C48—C552.6 (13)
C16—N2—C17—C24167.8 (7)C47—N4—C48—C495.8 (14)
Ni1—N2—C17—C243.4 (13)Ni2—N4—C48—C49178.9 (7)
C16—N2—C17—C1812.8 (13)N4—C48—C49—C5095.3 (11)
Ni1—N2—C17—C18176.0 (7)C55—C48—C49—C5088.2 (10)
N2—C17—C18—C1996.9 (10)N4—C48—C49—C5484.0 (11)
C24—C17—C18—C1982.6 (9)C55—C48—C49—C5492.5 (9)
N2—C17—C18—C2385.4 (11)C54—C49—C50—C511.3 (12)
C24—C17—C18—C2395.2 (9)C48—C49—C50—C51178.0 (7)
C23—C18—C19—C200.6 (11)C49—C50—C51—C520.2 (13)
C17—C18—C19—C20178.4 (6)C50—C51—C52—C531.5 (14)
C18—C19—C20—C210.5 (11)C51—C52—C53—C542.0 (15)
C19—C20—C21—C220.9 (11)C52—C53—C54—C490.8 (14)
C20—C21—C22—C231.4 (12)C50—C49—C54—C530.9 (12)
C21—C22—C23—C181.4 (12)C48—C49—C54—C53178.5 (7)
C19—C18—C23—C221.0 (11)N4—C48—C55—C6025.5 (13)
C17—C18—C23—C22178.8 (7)C49—C48—C55—C60151.1 (8)
N2—C17—C24—C25175.6 (9)N4—C48—C55—C56163.6 (9)
C18—C17—C24—C253.9 (12)C49—C48—C55—C5619.8 (12)
N2—C17—C24—C299.1 (13)C60—C55—C56—C570.5 (14)
C18—C17—C24—C29171.4 (9)C48—C55—C56—C57170.2 (8)
C29—C24—C25—C261.9 (14)C55—C56—C57—C582.5 (14)
C17—C24—C25—C26177.2 (8)C56—C57—C58—C592.6 (16)
C24—C25—C26—C271.0 (15)C57—C58—C59—C600.2 (15)
C25—C26—C27—C280.3 (17)Ni2—O4—C60—C5532.1 (12)
C26—C27—C28—C290.3 (17)Ni2—O4—C60—C59150.6 (6)
Ni1—O2—C29—C28162.6 (6)C56—C55—C60—O4179.5 (9)
Ni1—O2—C29—C2418.6 (15)C48—C55—C60—O49.7 (13)
C27—C28—C29—O2177.7 (10)C56—C55—C60—C593.2 (13)
C27—C28—C29—C241.1 (15)C48—C55—C60—C59167.6 (7)
C25—C24—C29—O2176.9 (9)C58—C59—C60—O4179.4 (9)
C17—C24—C29—O21.6 (15)C58—C59—C60—C553.1 (13)
C25—C24—C29—C281.8 (14)

Experimental details

Crystal data
Chemical formula[Ni(C31H28N2O2)]
Mr519.26
Crystal system, space groupMonoclinic, P21/c
Temperature (K)291
a, b, c (Å)23.722 (3), 9.4716 (6), 26.961 (4)
β (°) 124.319 (9)
V3)5003.2 (10)
Z8
Radiation typeMo Kα
µ (mm1)0.81
Crystal size (mm)0.24 × 0.12 × 0.08
Data collection
DiffractometerStoe IPDS 2T image-plate
diffractometer
Absorption correctionMulti-scan
[MULABS (Blessing, 1995) in PLATON (Spek, 2009)]
Tmin, Tmax0.830, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
23324, 8608, 2512
Rint0.117
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.053, 0.097, 0.61
No. of reflections8608
No. of parameters649
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.23, 0.24

Computer programs: X-AREA (Stoe & Cie, 2009), X-RED (Stoe & Cie, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Table 1. C—H···π interactions (Å, °) top
Cg2, Cg3 and Cg4 are the centroids of the C8–C23, C32–C37 and C55–C60 rings, respectively.
C—H···CgC—HH···CgC···CgC—H···Cg
C21-H21A···Cg2ii0.932.903.757 (11)153
C41-H41A···Cg3iii0.932.833.680 (12)153
C44-H44A···Cg4iv0.932.953.708 (10)149
C47-H47A···Cg4v0.932.923.884 (9)171
Symmetry codes: (ii) x, 3/2-y, 1/2+z; (iii) 1-x, 2-y, 1-z; (iv) 1-x, -1/2+y, 3/2-z; (v) 1-x, 1/2+y, 3/2-z.
 

Acknowledgements

HK and FF thank the PNU for financial support. RK thanks the Science and Research Branch, Islamic Azad University, Tehran, for support. MNT thanks Sargodha University for the research facility.

References

First citationAllen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.  CrossRef Web of Science Google Scholar
First citationBlessing, R. H. (1995). Acta Cryst. A51, 33–38.  CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationKargar, H., Kia, R., Jamshidvand, A. & Fun, H.-K. (2009). Acta Cryst. E65, o776–o777.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
First citationKargar, H., Kia, R., Ullah Khan, I. & Sahraei, A. (2010). Acta Cryst. E66, o539.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationStoe & Cie (2009). X-AREA and X-RED. Stoe & Cie, Darmstadt, Germany.  Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds