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

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ISSN: 2056-9890

{2,2′-[Cyclo­hexane-1,2-diylbis(nitrilo­methanyl­yl­idene)]diphenolato}copper(II)

aCollege of Chemistry and Chemical Engineering, Xi'an University of Science and Technology, Xi'an 710054, Shaanxi, People's Republic of China, and bCollege of Chemical Engineering, Northwest University, Xi'an 710069, Shaanxi, People's Republic of China
*Correspondence e-mail: shshzhao@xust.edu.cn

(Received 6 August 2012; accepted 21 August 2012; online 25 August 2012)

The title compound, [Cu(C20H20N2O2)], crystallizes with two independent mol­ecules in the asymmetric unit. In each mol­ecule, the CuII atom occupies the tetra­dentate N2O2 cavity of the salen-type Schiff base ligand, adopting a distorted square-planar geometry with r.m.s. deviations of the coordin­ating atoms of 0.0522 (2) and 0.1128 (4) Å. No hydrogen bonds or ππ stacking inter­action are observed.

Related literature

For biological activity of salen Schiff bases, see: Caboni et al. (2012[Caboni, L., Kinsella, G. K., Blanco, F., Fayne, D., Jagoe, W. N., Carr, M., Williams, D. C., Meegan, M. J. & Lloyd, D. G. (2012). J. Med. Chem. 55, 1635-1644.]). For the synthetic method, see: Marinovich et al. (1999[Marinovich, A. F., O'Mahony, R. S., Waters, J. M. & Waters, T. N. (1999). Croat. Chem. Acta, 72, 685-703.]); For related structures, see: Tang (2009[Tang, C. (2009). Acta Cryst. E65, m317.]); Ji & Lu (2010[Ji, X.-H. & Lu, J.-F. (2010). Acta Cryst. E66, m881.]).

[Scheme 1]

Experimental

Crystal data
  • [Cu(C20H20N2O2)]

  • Mr = 383.93

  • Monoclinic, P 21 /c

  • a = 12.254 (7) Å

  • b = 24.302 (14) Å

  • c = 12.297 (7) Å

  • β = 108.654 (9)°

  • V = 3469 (4) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 1.27 mm−1

  • T = 296 K

  • 0.38 × 0.24 × 0.21 mm

Data collection
  • Bruker SMART 1K CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2004[Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.]) Tmin = 0.700, Tmax = 0.765

  • 16804 measured reflections

  • 6164 independent reflections

  • 2285 reflections with I > 2σ(I)

  • Rint = 0.154

Refinement
  • R[F2 > 2σ(F2)] = 0.085

  • wR(F2) = 0.248

  • S = 0.95

  • 6164 reflections

  • 451 parameters

  • H-atom parameters constrained

  • Δρmax = 0.59 e Å−3

  • Δρmin = −0.91 e Å−3

Table 1
Selected bond lengths (Å)

Cu1—O2 1.859 (7)
Cu1—O1 1.897 (6)
Cu1—N1 1.920 (9)
Cu1—N2 1.954 (8)
Cu2—O3 1.868 (6)
Cu2—O4 1.893 (6)
Cu2—N4 1.907 (8)
Cu2—N3 1.929 (7)

Data collection: SMART (Bruker, 2001[Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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

Salen Schiff-bases and their metal complexes are of interest due to their biological activity, as well as their optical, catalytic, chromophoric, thermochromic and photochromic properties (Caboni et al., 2012). Here we report the crystal structure of salen-type Schiff-base copper complex. As Fig. 1 shows, the title compound crystallized with two independent molecules in the asymmetric unit. Each of the Cu atoms exists in ann almost planar coordination geometry and is placed in the center of the coordination plane, which is defined by four donor atoms (N1, N2, O1, O2 or N3, N4, O3, O4) of the Schiff-base ligand.

Related literature top

For biological activity of salen Schiff bases, see: Caboni et al. (2012). For the synthetic method, see: Marinovich et al. (1999); For related structures, see: Tang (2009); Ji et al. (2010).

Experimental top

The compound was prepared according to previous reported method (Marinovich et al., 1999). Crystals suitable for the X-ray diffraction study were obtained upon recrystallization from N,N-dimethylformamide.

Refinement top

H atoms were positioned geometrically and refined using a riding model with C—H = 0.95–0.99 Å and with Uiso(H) = 1.2 times Ueq(C).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (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 (I), with atom labels and 50% probability displacement ellipsoids for non-H atoms.
{2,2'-[Cyclohexane-1,2-diylbis(nitrilomethanylylidene)]diphenolato}copper(II) top
Crystal data top
[Cu(C20H20N2O2)]F(000) = 1592
Mr = 383.93Dx = 1.470 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5789 reflections
a = 12.254 (7) Åθ = 1.9–25.3°
b = 24.302 (14) ŵ = 1.27 mm1
c = 12.297 (7) ÅT = 296 K
β = 108.654 (9)°Block, dark green
V = 3469 (4) Å30.38 × 0.24 × 0.21 mm
Z = 8
Data collection top
Bruker SMART 1K CCD area-detector
diffractometer
6164 independent reflections
Radiation source: fine-focus sealed tube2285 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.154
Thin–slice ω scansθmax = 25.1°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)
h = 1214
Tmin = 0.700, Tmax = 0.765k = 2820
16804 measured reflectionsl = 1414
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)] = 0.085Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.248H-atom parameters constrained
S = 0.95 w = 1/[σ2(Fo2) + (0.0984P)2]
where P = (Fo2 + 2Fc2)/3
6164 reflections(Δ/σ)max < 0.001
451 parametersΔρmax = 0.59 e Å3
0 restraintsΔρmin = 0.91 e Å3
Crystal data top
[Cu(C20H20N2O2)]V = 3469 (4) Å3
Mr = 383.93Z = 8
Monoclinic, P21/cMo Kα radiation
a = 12.254 (7) ŵ = 1.27 mm1
b = 24.302 (14) ÅT = 296 K
c = 12.297 (7) Å0.38 × 0.24 × 0.21 mm
β = 108.654 (9)°
Data collection top
Bruker SMART 1K CCD area-detector
diffractometer
6164 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)
2285 reflections with I > 2σ(I)
Tmin = 0.700, Tmax = 0.765Rint = 0.154
16804 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0850 restraints
wR(F2) = 0.248H-atom parameters constrained
S = 0.95Δρmax = 0.59 e Å3
6164 reflectionsΔρmin = 0.91 e Å3
451 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
Cu20.07642 (10)0.68998 (5)0.02055 (9)0.0691 (5)
Cu10.65609 (10)0.52703 (5)0.00444 (9)0.0730 (5)
N30.0935 (6)0.6996 (3)0.1397 (6)0.0561 (19)
O10.6408 (6)0.5123 (3)0.1601 (5)0.0772 (19)
O40.0387 (6)0.6869 (3)0.1822 (5)0.079 (2)
O20.6494 (5)0.6020 (3)0.0361 (5)0.0737 (19)
O30.2034 (6)0.7338 (3)0.0150 (5)0.087 (2)
N20.6614 (6)0.5371 (4)0.1548 (6)0.068 (2)
N40.0362 (6)0.6365 (3)0.0166 (6)0.065 (2)
N10.6748 (7)0.4505 (4)0.0359 (7)0.073 (2)
C270.1706 (9)0.7314 (4)0.2108 (7)0.063 (3)
H9A0.16790.73450.28530.075*
C70.6501 (8)0.4090 (5)0.0335 (9)0.075 (3)
H10A0.65300.37400.00180.089*
C330.2746 (10)0.7626 (4)0.0725 (7)0.076 (3)
C350.1253 (8)0.6263 (4)0.2210 (8)0.064 (3)
C280.2585 (8)0.7616 (4)0.1829 (7)0.059 (2)
C60.6184 (8)0.4131 (5)0.1561 (9)0.071 (3)
C260.0031 (9)0.6724 (4)0.1748 (7)0.072 (3)
H15A0.06440.69660.15230.086*
C290.3376 (9)0.7924 (4)0.2709 (8)0.073 (3)
H16A0.32870.79270.34320.087*
C90.8436 (9)0.4491 (4)0.2040 (8)0.087 (3)
H17A0.86280.48440.17790.104*
H17B0.88070.42050.17350.104*
C360.0496 (10)0.6608 (4)0.2540 (9)0.074 (3)
C140.6652 (8)0.5840 (5)0.2028 (8)0.077 (3)
H19A0.66500.58360.27830.092*
C300.4247 (9)0.8213 (4)0.2556 (9)0.083 (3)
H20A0.47540.84110.31540.099*
C150.6698 (8)0.6367 (5)0.1546 (8)0.066 (3)
C100.8874 (10)0.4472 (5)0.3359 (9)0.101 (4)
H22A0.96970.45410.36330.121*
H22B0.87410.41080.36160.121*
C340.1134 (8)0.6147 (4)0.1020 (8)0.071 (3)
H23A0.16470.59000.08670.085*
C80.7139 (9)0.4409 (4)0.1610 (8)0.079 (3)
H25A0.69370.40370.17860.095*
C200.6627 (8)0.6437 (5)0.0351 (8)0.070 (3)
C210.0296 (8)0.6198 (4)0.1019 (7)0.067 (3)
H27A0.10440.60610.10290.081*
C250.0285 (10)0.6593 (5)0.3008 (8)0.093 (4)
H28A0.04110.64600.31340.112*
H28B0.05230.69260.34560.112*
C320.3642 (10)0.7920 (5)0.0599 (8)0.095 (4)
H29A0.37570.79210.01130.114*
C130.6537 (9)0.4835 (5)0.2104 (8)0.080 (3)
H30A0.57210.47340.18660.096*
C220.0633 (9)0.5749 (4)0.1442 (9)0.085 (3)
H31A0.03700.54110.10170.102*
H31B0.13340.58640.13040.102*
C370.0656 (10)0.6652 (4)0.3730 (8)0.086 (3)
H32A0.01730.68780.39820.103*
C400.2150 (10)0.5986 (4)0.3064 (10)0.094 (3)
H33A0.26520.57570.28450.112*
C380.1520 (10)0.6365 (5)0.4513 (8)0.089 (3)
H34A0.15820.63860.52860.106*
C40.5544 (10)0.3658 (6)0.3380 (11)0.097 (4)
H35A0.53300.33340.37950.117*
C310.4363 (9)0.8206 (5)0.1457 (9)0.089 (3)
H36A0.49560.84060.13230.107*
C50.5867 (9)0.3652 (5)0.2215 (10)0.086 (3)
H37A0.58790.33180.18410.104*
C110.8252 (10)0.4904 (5)0.3863 (9)0.095 (4)
H38A0.85230.48760.46940.114*
H38B0.84370.52690.36570.114*
C230.0879 (10)0.5643 (5)0.2720 (10)0.100 (4)
H39A0.01940.54940.28440.120*
H39B0.14860.53700.29760.120*
C240.1237 (11)0.6157 (5)0.3420 (9)0.101 (4)
H40A0.19490.62960.33390.121*
H40B0.13700.60750.42240.121*
C20.5839 (9)0.4640 (5)0.3347 (8)0.088 (3)
H47A0.58440.49650.37450.106*
C190.6704 (9)0.6972 (5)0.0004 (10)0.084 (3)
H42A0.66550.70280.07670.101*
C10.6139 (9)0.4644 (5)0.2133 (9)0.075 (3)
C180.6845 (9)0.7424 (5)0.0686 (11)0.094 (4)
H43A0.69020.77740.04020.113*
C170.6903 (10)0.7347 (5)0.1852 (11)0.097 (4)
H45A0.69780.76480.23370.116*
C160.6847 (10)0.6836 (6)0.2241 (9)0.094 (4)
H44A0.69090.67910.30090.113*
C30.5537 (10)0.4146 (6)0.3935 (10)0.102 (4)
H48A0.53240.41470.47320.123*
C390.2283 (10)0.6053 (5)0.4203 (10)0.099 (4)
H49A0.28930.58850.47590.119*
C120.6981 (9)0.4823 (5)0.3433 (9)0.092 (3)
H50A0.66090.51120.37300.110*
H50B0.67880.44730.37020.110*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu20.0735 (9)0.0951 (9)0.0377 (6)0.0100 (8)0.0163 (5)0.0016 (6)
Cu10.0678 (9)0.0969 (10)0.0496 (7)0.0040 (8)0.0120 (6)0.0010 (6)
N30.046 (5)0.082 (5)0.044 (4)0.004 (4)0.019 (4)0.006 (4)
O10.076 (5)0.097 (5)0.051 (4)0.007 (4)0.010 (3)0.005 (4)
O40.079 (5)0.108 (5)0.050 (4)0.032 (4)0.020 (3)0.008 (4)
O20.077 (5)0.096 (5)0.047 (4)0.001 (4)0.016 (3)0.001 (3)
O30.089 (5)0.145 (6)0.029 (3)0.047 (5)0.019 (3)0.001 (4)
N20.052 (5)0.090 (6)0.053 (5)0.012 (5)0.002 (4)0.009 (5)
N40.060 (5)0.092 (6)0.044 (4)0.007 (5)0.019 (4)0.001 (4)
N10.063 (6)0.093 (6)0.058 (5)0.001 (5)0.012 (4)0.006 (5)
C270.081 (7)0.076 (7)0.029 (4)0.002 (6)0.015 (5)0.001 (4)
C70.052 (6)0.097 (8)0.077 (7)0.001 (6)0.026 (6)0.003 (6)
C330.083 (8)0.095 (8)0.040 (5)0.006 (7)0.007 (5)0.006 (5)
C350.048 (6)0.081 (7)0.056 (6)0.004 (6)0.005 (5)0.006 (5)
C280.062 (6)0.063 (6)0.048 (5)0.001 (5)0.012 (5)0.010 (5)
C60.049 (6)0.101 (8)0.066 (7)0.004 (6)0.023 (5)0.011 (7)
C260.072 (7)0.107 (8)0.046 (5)0.001 (6)0.032 (5)0.001 (5)
C290.072 (7)0.094 (8)0.046 (5)0.006 (7)0.008 (5)0.008 (5)
C90.088 (9)0.102 (8)0.061 (6)0.018 (7)0.010 (6)0.005 (6)
C360.077 (8)0.079 (7)0.065 (6)0.014 (7)0.022 (6)0.007 (6)
C140.075 (8)0.097 (9)0.053 (6)0.021 (7)0.012 (5)0.001 (6)
C300.060 (7)0.102 (9)0.073 (7)0.016 (7)0.005 (6)0.013 (6)
C150.056 (6)0.083 (7)0.054 (6)0.001 (6)0.011 (5)0.010 (6)
C100.094 (9)0.125 (10)0.064 (7)0.010 (8)0.000 (6)0.022 (7)
C340.055 (6)0.096 (7)0.059 (6)0.014 (6)0.015 (5)0.004 (6)
C80.081 (8)0.091 (8)0.054 (6)0.008 (7)0.006 (6)0.008 (6)
C200.056 (7)0.091 (8)0.056 (6)0.010 (6)0.006 (5)0.006 (6)
C210.054 (6)0.098 (8)0.048 (5)0.002 (6)0.014 (5)0.011 (5)
C250.097 (9)0.136 (10)0.054 (6)0.026 (9)0.035 (6)0.000 (7)
C320.091 (9)0.140 (10)0.047 (6)0.047 (8)0.013 (6)0.009 (6)
C130.075 (8)0.109 (9)0.053 (6)0.012 (7)0.018 (6)0.003 (6)
C220.076 (8)0.097 (8)0.075 (7)0.006 (7)0.015 (6)0.014 (6)
C370.107 (9)0.109 (8)0.040 (5)0.002 (7)0.021 (6)0.002 (6)
C400.094 (9)0.101 (9)0.076 (8)0.013 (7)0.013 (7)0.001 (7)
C380.094 (9)0.117 (9)0.043 (5)0.000 (8)0.004 (6)0.017 (6)
C40.083 (9)0.129 (11)0.086 (9)0.005 (9)0.036 (7)0.040 (8)
C310.072 (7)0.123 (10)0.065 (7)0.019 (7)0.012 (6)0.008 (7)
C50.083 (8)0.087 (8)0.098 (9)0.005 (7)0.041 (7)0.016 (7)
C110.115 (10)0.093 (8)0.071 (7)0.007 (8)0.022 (7)0.005 (6)
C230.084 (8)0.122 (10)0.085 (8)0.008 (8)0.016 (7)0.039 (8)
C240.102 (10)0.132 (10)0.059 (7)0.030 (9)0.012 (7)0.021 (7)
C20.081 (8)0.133 (10)0.051 (6)0.000 (8)0.023 (6)0.009 (7)
C190.092 (9)0.083 (8)0.075 (7)0.007 (7)0.022 (6)0.003 (7)
C10.059 (7)0.101 (9)0.066 (7)0.006 (7)0.020 (6)0.003 (7)
C180.075 (8)0.102 (10)0.100 (10)0.005 (7)0.019 (7)0.014 (8)
C170.092 (9)0.095 (9)0.095 (10)0.004 (8)0.016 (7)0.018 (8)
C160.096 (9)0.116 (10)0.061 (7)0.020 (9)0.010 (6)0.002 (8)
C30.094 (9)0.136 (11)0.068 (8)0.002 (9)0.015 (7)0.040 (9)
C390.079 (9)0.139 (11)0.061 (7)0.019 (8)0.002 (6)0.023 (7)
C120.074 (8)0.132 (10)0.071 (7)0.004 (7)0.025 (6)0.007 (7)
Geometric parameters (Å, º) top
Cu2—O31.868 (6)C10—H22B0.9700
Cu2—O41.893 (6)C34—H23A0.9300
Cu2—N41.907 (8)C8—C131.507 (13)
Cu2—N31.929 (7)C8—H25A0.9800
Cu1—O21.859 (7)C20—C191.386 (13)
Cu1—O11.897 (6)C21—C221.543 (12)
Cu1—N11.920 (9)C21—H27A0.9800
Cu1—N21.954 (8)C25—C241.537 (14)
N3—C271.312 (10)C25—H28A0.9700
N3—C261.468 (11)C25—H28B0.9700
O1—C11.325 (11)C32—C311.336 (13)
O4—C361.320 (11)C32—H29A0.9300
O2—C201.315 (11)C13—C121.548 (12)
O3—C331.345 (11)C13—H30A0.9800
N2—C141.278 (11)C22—C231.524 (13)
N2—C131.488 (12)C22—H31A0.9700
N4—C341.283 (10)C22—H31B0.9700
N4—C211.489 (10)C37—C381.372 (13)
N1—C71.293 (11)C37—H32A0.9300
N1—C81.475 (11)C40—C391.367 (14)
C27—C281.434 (12)C40—H33A0.9300
C27—H9A0.9300C38—C391.350 (14)
C7—C61.435 (12)C38—H34A0.9300
C7—H10A0.9300C4—C51.359 (14)
C33—C321.359 (13)C4—C31.366 (15)
C33—C281.434 (12)C4—H35A0.9300
C35—C361.404 (12)C31—H36A0.9300
C35—C401.423 (13)C5—H37A0.9300
C35—C341.451 (12)C11—C121.489 (13)
C28—C291.414 (12)C11—H38A0.9700
C6—C51.398 (13)C11—H38B0.9700
C6—C11.423 (13)C23—C241.501 (14)
C26—C251.514 (11)C23—H39A0.9700
C26—C211.539 (12)C23—H39B0.9700
C26—H15A0.9800C24—H40A0.9700
C29—C301.340 (13)C24—H40B0.9700
C29—H16A0.9300C2—C31.390 (14)
C9—C81.519 (13)C2—C11.418 (13)
C9—C101.537 (12)C2—H47A0.9300
C9—H17A0.9700C19—C181.364 (14)
C9—H17B0.9700C19—H42A0.9300
C36—C371.417 (12)C18—C171.425 (15)
C14—C151.418 (13)C18—H43A0.9300
C14—H19A0.9300C17—C161.340 (14)
C30—C311.404 (13)C17—H45A0.9300
C30—H20A0.9300C16—H44A0.9300
C15—C161.402 (13)C3—H48A0.9300
C15—C201.454 (12)C39—H49A0.9300
C10—C111.539 (14)C12—H50A0.9700
C10—H22A0.9700C12—H50B0.9700
O3—Cu2—O489.0 (3)N4—C21—C22109.0 (7)
O3—Cu2—N4171.1 (3)C26—C21—C22111.5 (8)
O4—Cu2—N493.7 (3)N4—C21—H27A110.3
O3—Cu2—N394.4 (3)C26—C21—H27A110.3
O4—Cu2—N3171.2 (3)C22—C21—H27A110.3
N4—Cu2—N384.2 (3)C26—C25—C24111.6 (9)
O2—Cu1—O189.4 (3)C26—C25—H28A109.3
O2—Cu1—N1175.6 (3)C24—C25—H28A109.3
O1—Cu1—N192.5 (3)C26—C25—H28B109.3
O2—Cu1—N294.1 (3)C24—C25—H28B109.3
O1—Cu1—N2174.9 (3)H28A—C25—H28B108.0
N1—Cu1—N284.2 (4)C31—C32—C33122.6 (11)
C27—N3—C26121.2 (7)C31—C32—H29A118.7
C27—N3—Cu2124.9 (6)C33—C32—H29A118.7
C26—N3—Cu2113.6 (5)N2—C13—C8107.8 (8)
C1—O1—Cu1126.3 (6)N2—C13—C12116.7 (9)
C36—O4—Cu2126.4 (6)C8—C13—C12111.1 (8)
C20—O2—Cu1128.8 (6)N2—C13—H30A106.9
C33—O3—Cu2130.3 (6)C8—C13—H30A106.9
C14—N2—C13124.6 (9)C12—C13—H30A106.9
C14—N2—Cu1124.0 (7)C23—C22—C21110.4 (9)
C13—N2—Cu1111.3 (6)C23—C22—H31A109.6
C34—N4—C21118.9 (8)C21—C22—H31A109.6
C34—N4—Cu2127.7 (7)C23—C22—H31B109.6
C21—N4—Cu2113.4 (6)C21—C22—H31B109.6
C7—N1—C8119.7 (9)H31A—C22—H31B108.1
C7—N1—Cu1127.0 (7)C38—C37—C36120.5 (11)
C8—N1—Cu1113.2 (7)C38—C37—H32A119.8
N3—C27—C28125.3 (8)C36—C37—H32A119.8
N3—C27—H9A117.4C39—C40—C35120.7 (11)
C28—C27—H9A117.4C39—C40—H33A119.6
N1—C7—C6124.5 (10)C35—C40—H33A119.6
N1—C7—H10A117.8C39—C38—C37122.4 (10)
C6—C7—H10A117.8C39—C38—H34A118.8
O3—C33—C32121.6 (9)C37—C38—H34A118.8
O3—C33—C28119.8 (10)C5—C4—C3119.3 (12)
C32—C33—C28118.6 (9)C5—C4—H35A120.3
C36—C35—C40119.7 (10)C3—C4—H35A120.3
C36—C35—C34123.0 (8)C32—C31—C30121.4 (11)
C40—C35—C34117.2 (10)C32—C31—H36A119.3
C29—C28—C27118.2 (9)C30—C31—H36A119.3
C29—C28—C33116.5 (9)C4—C5—C6122.1 (11)
C27—C28—C33125.3 (9)C4—C5—H37A119.0
C5—C6—C1119.0 (10)C6—C5—H37A119.0
C5—C6—C7118.6 (11)C12—C11—C10111.3 (10)
C1—C6—C7122.4 (10)C12—C11—H38A109.4
N3—C26—C25117.9 (8)C10—C11—H38A109.4
N3—C26—C21106.4 (7)C12—C11—H38B109.4
C25—C26—C21110.6 (8)C10—C11—H38B109.4
N3—C26—H15A107.1H38A—C11—H38B108.0
C25—C26—H15A107.1C24—C23—C22112.1 (9)
C21—C26—H15A107.1C24—C23—H39A109.2
C30—C29—C28123.5 (10)C22—C23—H39A109.2
C30—C29—H16A118.2C24—C23—H39B109.2
C28—C29—H16A118.2C22—C23—H39B109.2
C8—C9—C10109.7 (9)H39A—C23—H39B107.9
C8—C9—H17A109.7C23—C24—C25109.5 (9)
C10—C9—H17A109.7C23—C24—H40A109.8
C8—C9—H17B109.7C25—C24—H40A109.8
C10—C9—H17B109.7C23—C24—H40B109.8
H17A—C9—H17B108.2C25—C24—H40B109.8
O4—C36—C35124.8 (9)H40A—C24—H40B108.2
O4—C36—C37117.9 (10)C3—C2—C1119.3 (11)
C35—C36—C37117.3 (9)C3—C2—H47A120.3
N2—C14—C15127.8 (9)C1—C2—H47A120.3
N2—C14—H19A116.1C18—C19—C20124.6 (11)
C15—C14—H19A116.1C18—C19—H42A117.7
C29—C30—C31117.3 (10)C20—C19—H42A117.7
C29—C30—H20A121.3O1—C1—C2117.7 (10)
C31—C30—H20A121.3O1—C1—C6124.1 (9)
C16—C15—C14119.6 (10)C2—C1—C6118.1 (10)
C16—C15—C20118.3 (10)C19—C18—C17118.5 (11)
C14—C15—C20122.0 (9)C19—C18—H43A120.8
C9—C10—C11110.7 (8)C17—C18—H43A120.8
C9—C10—H22A109.5C16—C17—C18119.2 (11)
C11—C10—H22A109.5C16—C17—H45A120.4
C9—C10—H22B109.5C18—C17—H45A120.4
C11—C10—H22B109.5C17—C16—C15123.2 (11)
H22A—C10—H22B108.1C17—C16—H44A118.4
N4—C34—C35123.7 (9)C15—C16—H44A118.4
N4—C34—H23A118.2C4—C3—C2122.1 (11)
C35—C34—H23A118.2C4—C3—H48A119.0
N1—C8—C13105.9 (8)C2—C3—H48A119.0
N1—C8—C9107.3 (8)C38—C39—C40119.3 (10)
C13—C8—C9111.2 (9)C38—C39—H49A120.3
N1—C8—H25A110.7C40—C39—H49A120.3
C13—C8—H25A110.7C11—C12—C13110.3 (9)
C9—C8—H25A110.7C11—C12—H50A109.6
O2—C20—C19121.3 (9)C13—C12—H50A109.6
O2—C20—C15122.5 (10)C11—C12—H50B109.6
C19—C20—C15116.1 (10)C13—C12—H50B109.6
N4—C21—C26105.5 (7)H50A—C12—H50B108.1

Experimental details

Crystal data
Chemical formula[Cu(C20H20N2O2)]
Mr383.93
Crystal system, space groupMonoclinic, P21/c
Temperature (K)296
a, b, c (Å)12.254 (7), 24.302 (14), 12.297 (7)
β (°) 108.654 (9)
V3)3469 (4)
Z8
Radiation typeMo Kα
µ (mm1)1.27
Crystal size (mm)0.38 × 0.24 × 0.21
Data collection
DiffractometerBruker SMART 1K CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2004)
Tmin, Tmax0.700, 0.765
No. of measured, independent and
observed [I > 2σ(I)] reflections
16804, 6164, 2285
Rint0.154
(sin θ/λ)max1)0.597
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.085, 0.248, 0.95
No. of reflections6164
No. of parameters451
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.59, 0.91

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top
Cu2—O31.868 (6)Cu1—O21.859 (7)
Cu2—O41.893 (6)Cu1—O11.897 (6)
Cu2—N41.907 (8)Cu1—N11.920 (9)
Cu2—N31.929 (7)Cu1—N21.954 (8)
 

Acknowledgements

The project was supported by the National Natural Science Foundation of China (program Nos. 21103135 and 21073139), the Natural Science Basic Research Plan in Shaanxi Province of China (program No. 2011JQ2011), the Scientific Research Program Funded by Shaanxi Provincial Education Department (program No. 12 J K0622) and the Grant of Xi'an University of Science and Technology (program No. 2010QDJ030).

References

First citationBruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationCaboni, L., Kinsella, G. K., Blanco, F., Fayne, D., Jagoe, W. N., Carr, M., Williams, D. C., Meegan, M. J. & Lloyd, D. G. (2012). J. Med. Chem. 55, 1635–1644.  Web of Science CrossRef CAS PubMed
First citationJi, X.-H. & Lu, J.-F. (2010). Acta Cryst. E66, m881.  Web of Science CSD CrossRef IUCr Journals
First citationMarinovich, A. F., O'Mahony, R. S., Waters, J. M. & Waters, T. N. (1999). Croat. Chem. Acta, 72, 685–703.  CAS
First citationSheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationTang, C. (2009). Acta Cryst. E65, m317.  Web of Science CSD CrossRef IUCr Journals

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