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Acta Crystallogr Sect E Struct Rep Online. 2009 August 1; 65(Pt 8): m858.
Published online 2009 July 1. doi:  10.1107/S1600536809024428
PMCID: PMC2977238

Aqua­(furan-2-carboxyl­ato-κO)(furan-2-carboxyl­ato-κ2 O,O′)(1,10-phenanthroline-κ2 N,N′)copper(II) methanol hemisolvate

Abstract

The asymmetric unit of the title compound, [Cu(C5H3O3)2(C12H8N2)2(H2O)]·0.5CH3OH, contains two CuII complex mol­ecules and one methanol solvent mol­ecule with the metal centres in strongly distorted octahedral coordination. The coordinated water mol­ecule is involved in inter­molecular O—H(...)O hydrogen bonding, which links the complex mol­ecules into chains propagating along the c axis. Neighbouring chains inter­act further via π–π inter­actions between the aromatic rings of 1,10-phenanthroline fragments [centroid–centroid distances = 3.726 (4) and 3.750 (4) Å].

Related literature

For the crystal structures of related carboxyl­ate complexes with 1,10-phenanthroline, see: Ai et al. (2007 [triangle]); Li et al. (2007 [triangle]); Rodrigues (2004 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0m858-scheme1.jpg

Experimental

Crystal data

  • [Cu(C5H3O3)2(C12H8N2)2(H2O)]·0.5CH4O
  • M r = 499.93
  • Tetragonal, An external file that holds a picture, illustration, etc.
Object name is e-65-0m858-efi1.jpg
  • a = 34.129 (17) Å
  • c = 14.450 (6) Å
  • V = 16831 (14) Å3
  • Z = 32
  • Mo Kα radiation
  • μ = 1.09 mm−1
  • T = 273 K
  • 0.28 × 0.22 × 0.17 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.750, T max = 0.836
  • 43834 measured reflections
  • 7448 independent reflections
  • 4004 reflections with I > 2σ(I)
  • R int = 0.100

Refinement

  • R[F 2 > 2σ(F 2)] = 0.055
  • wR(F 2) = 0.169
  • S = 0.97
  • 7448 reflections
  • 595 parameters
  • 792 restraints
  • H-atom parameters constrained
  • Δρmax = 0.60 e Å−3
  • Δρmin = −0.54 e Å−3

Data collection: SMART (Siemens, 1996 [triangle]); cell refinement: SAINT (Siemens, 1996 [triangle]); data reduction: SAINT; 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.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809024428/cv2568sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809024428/cv2568Isup2.hkl

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

Acknowledgments

The authors thank the Postgraduate Foundation of Taishan University for financial support (grant No. Y07–2–15).

supplementary crystallographic information

Comment

Metal complexes with carboxylates are among the most investigated complexes in the field of coordination chemistry. In recent years, more and more attentions begin to be inclined to complexes with mixed-ligands such as 1,10-phenanthroline ligand (Ai et al., 2007; Li et al., 2007; Rodrigues, 2004). We selected a new carboxylic ligand with the cupric acetate in the presence of 1,10-phenanthroline co-ligand and obtained the title compound, (I).

In (I), the Cu centers exhibit a six-coordinated octahedron geometry with three O atoms from two carboxylic ligands[Cu—O 1.946 (4)–2.255 (4) Å] and one water molecule (Cu—O 1.937 (4)/%A) and two N atoms [Cu—N 2.011 (4), 2.023 (4)/%A] from 1,10-phenanthroline ligand. The crystal packing exhibits intra- and intermolecular O—H···O hydrogen bonds (Table 1). The latter link the complex molecules into a one-dimensional infinite chain structure.

Experimental

The reaction was carried out in 30 ml me thanol solvent. furan-2-carboxylic acid(0.224 g,2 mmol) and cupric acetate(0.199 g, 1 mmol) and 1,10-phenanthroline(0.180 g, 1 mmol) were mixed in the methanol solvent and stirred for 6 h. The resulting blue solution was filtered. The filtrate was placed for sevaral days yielding blue crystals.

The yield is 76% and elemental analysis: calc. for C45H36Cu2N4O15: C 54.05, H 3.63, N 5.60; found: C 54.32, H 3.39, N 5.22. The elemental analyses were performed with PERKIN ELMER MODEL 2400 SERIES II.

Refinement

C-bound H atoms were placed in idealized positions, with C—H = 0.93/%A and Uiso(H) = 1.2Ueq(C). O-bound H atoms were located in a difference Fourier map, but placed in idealized positions (O—H 0.82-0.85 Å) and refined as riding, with Uiso(H) = 1.2Ueq(O).

Figures

Fig. 1.
The content of asymmetric unit of the title compound, with atomic numbering and 30% probability displacement ellipsoids.

Crystal data

[Cu(C5H3O3)2(C12H8N2)(H2O)]·0.5CH4ODx = 1.578 Mg m3
Mr = 499.93Mo Kα radiation, λ = 0.71073 Å
Tetragonal, I41/aCell parameters from 2700 reflections
a = 34.129 (17) Åθ = 2.3–17.6°
c = 14.450 (6) ŵ = 1.09 mm1
V = 16831 (14) Å3T = 273 K
Z = 32Block, blue
F(000) = 81920.28 × 0.22 × 0.17 mm

Data collection

Bruker SMART APEX diffractometer7448 independent reflections
Radiation source: fine-focus sealed tube4004 reflections with I > 2σ(I)
graphiteRint = 0.100
[var phi] and ω scansθmax = 25.1°, θmin = 1.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −24→40
Tmin = 0.750, Tmax = 0.836k = −40→40
43834 measured reflectionsl = −17→17

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)] = 0.055Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.169H-atom parameters constrained
S = 0.97w = 1/[σ2(Fo2) + (0.0667P)2 + 46.5236P] where P = (Fo2 + 2Fc2)/3
7448 reflections(Δ/σ)max = 0.067
595 parametersΔρmax = 0.60 e Å3
792 restraintsΔρmin = −0.54 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
Cu10.41922 (2)0.92317 (2)0.34020 (6)0.0567 (3)
Cu20.40266 (2)0.93097 (2)0.83960 (5)0.0545 (3)
N10.47730 (13)0.93179 (14)0.3495 (3)0.0526 (12)
N20.41904 (14)0.98143 (13)0.3637 (3)0.0537 (13)
N30.46157 (13)0.93354 (14)0.8468 (4)0.0584 (13)
N40.40865 (13)0.98941 (13)0.8544 (3)0.0522 (12)
O10.36304 (12)0.92475 (12)0.3225 (3)0.0682 (12)
O20.34551 (14)0.87386 (14)0.4113 (4)0.0920 (17)
O30.26925 (14)0.88894 (14)0.3840 (4)0.0917 (16)
O40.42538 (14)0.87018 (14)0.2810 (4)0.0790 (14)
O50.42095 (15)0.90712 (16)0.1585 (4)0.0922 (15)
O60.42574 (16)0.8048 (2)0.1759 (4)0.1119 (19)
O70.34659 (11)0.93629 (11)0.8196 (3)0.0611 (11)
O80.32803 (13)0.89471 (14)0.9321 (4)0.0826 (15)
O90.25254 (13)0.90035 (13)0.8808 (4)0.0809 (14)
O100.40450 (12)0.87529 (11)0.8105 (3)0.0622 (11)
O110.41060 (14)0.89599 (13)0.6660 (3)0.0758 (13)
O120.41274 (16)0.79989 (13)0.7609 (4)0.0909 (16)
O130.41769 (13)0.89163 (13)0.4768 (3)0.0825 (14)
H13A0.39460.88440.46310.099*
H13B0.41590.90070.53150.099*
O140.39486 (14)0.92340 (14)0.9930 (4)0.1002 (17)
H14A0.38570.90200.97160.120*
H14B0.40410.91771.04600.120*
O150.4487 (5)0.8142 (3)0.3748 (11)0.374 (11)
H150.43040.82330.34500.561*
C10.29690 (19)0.91197 (19)0.3408 (5)0.0633 (17)
C20.2805 (2)0.9406 (2)0.2934 (6)0.081 (2)
H20.29300.96000.25910.097*
C30.2386 (2)0.9356 (3)0.3055 (6)0.093 (2)
H30.21870.95090.28030.112*
C40.2345 (2)0.9050 (3)0.3605 (7)0.099 (2)
H40.21040.89550.38040.119*
C50.33834 (19)0.9016 (2)0.3615 (5)0.0671 (18)
C60.42439 (19)0.8399 (2)0.1322 (7)0.079 (2)
C70.4270 (2)0.8336 (2)0.0467 (7)0.091 (2)
H70.42630.85390.00360.109*
C80.4283 (2)0.7958 (3)0.0253 (8)0.113 (3)
H80.43020.7845−0.03320.135*
C90.4272 (3)0.7777 (3)0.1052 (9)0.115 (3)
H90.42760.75070.11230.138*
C100.42390 (18)0.8749 (2)0.1990 (6)0.0709 (18)
C110.50628 (18)0.90624 (19)0.3447 (5)0.0655 (17)
H110.50010.87990.33680.079*
C120.54568 (19)0.9165 (2)0.3516 (5)0.0683 (18)
H120.56510.89750.34870.082*
C130.55537 (19)0.9543 (2)0.3620 (5)0.0677 (17)
H130.58160.96160.36480.081*
C140.52599 (18)0.98333 (19)0.3684 (4)0.0575 (15)
C150.5328 (2)1.0239 (2)0.3838 (5)0.0686 (17)
H15A0.55851.03290.38860.082*
C160.5032 (2)1.04922 (19)0.3911 (5)0.0698 (17)
H160.50861.07560.40020.084*
C170.46328 (19)1.03649 (18)0.3853 (4)0.0603 (16)
C180.4303 (2)1.0611 (2)0.3938 (5)0.0731 (18)
H180.43351.08770.40430.088*
C190.3941 (2)1.0457 (2)0.3873 (5)0.0776 (19)
H190.37241.06200.39270.093*
C200.3887 (2)1.00561 (19)0.3720 (5)0.0690 (18)
H200.36340.99560.36800.083*
C210.45586 (17)0.99693 (16)0.3707 (4)0.0504 (14)
C220.48726 (17)0.96997 (17)0.3627 (4)0.0493 (14)
C230.28030 (18)0.92319 (18)0.8385 (5)0.0574 (16)
C240.26325 (19)0.9482 (2)0.7801 (5)0.0709 (18)
H240.27560.96670.74270.085*
C250.2217 (2)0.9409 (2)0.7866 (6)0.082 (2)
H250.20170.95400.75550.099*
C260.2175 (2)0.9119 (2)0.8455 (6)0.084 (2)
H260.19360.90060.86120.101*
C270.32148 (18)0.91669 (17)0.8667 (5)0.0580 (16)
C280.41337 (16)0.82819 (17)0.6946 (5)0.0533 (15)
C290.41773 (17)0.81258 (18)0.6102 (5)0.0629 (17)
H290.41910.82590.55410.075*
C300.4200 (2)0.7715 (2)0.6235 (6)0.080 (2)
H300.42310.75250.57810.097*
C310.4168 (2)0.7659 (2)0.7131 (6)0.094 (2)
H310.41720.74130.74070.112*
C320.40934 (17)0.86949 (18)0.7240 (5)0.0567 (16)
C330.48763 (18)0.90588 (19)0.8414 (5)0.0701 (18)
H330.47880.88030.83310.084*
C340.52802 (19)0.9110 (2)0.8497 (5)0.0757 (19)
H340.54540.89010.84610.091*
C350.54161 (19)0.9475 (2)0.8621 (5)0.0701 (18)
H350.56840.95190.86580.084*
C360.51533 (19)0.97918 (19)0.8692 (4)0.0614 (16)
C370.52598 (19)1.0189 (2)0.8857 (5)0.0694 (17)
H370.55241.02540.89090.083*
C380.4990 (2)1.0473 (2)0.8937 (5)0.0713 (18)
H380.50721.07280.90540.086*
C390.45792 (18)1.03930 (18)0.8848 (4)0.0580 (15)
C400.4279 (2)1.06707 (18)0.8917 (5)0.0650 (17)
H400.43391.09310.90480.078*
C410.3902 (2)1.05618 (19)0.8798 (5)0.0681 (17)
H410.37031.07470.88400.082*
C420.38101 (18)1.01689 (18)0.8599 (4)0.0613 (16)
H420.35501.00990.85090.074*
C430.44656 (17)1.00040 (17)0.8670 (4)0.0519 (14)
C440.47548 (17)0.97014 (18)0.8604 (4)0.0522 (14)
C450.44756 (18)0.7762 (3)0.3692 (8)0.217 (7)
H45A0.47060.76600.39860.325*
H45B0.44880.77100.30390.325*
H45C0.42480.76380.39480.325*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cu10.0515 (5)0.0466 (4)0.0721 (6)0.0005 (3)−0.0048 (4)−0.0029 (4)
Cu20.0478 (4)0.0464 (4)0.0693 (6)−0.0023 (3)−0.0005 (4)−0.0026 (4)
N10.046 (3)0.051 (3)0.061 (3)0.009 (2)−0.004 (2)−0.001 (2)
N20.047 (3)0.046 (3)0.068 (4)0.007 (2)0.002 (2)0.000 (2)
N30.047 (3)0.050 (3)0.079 (4)0.005 (2)0.001 (3)−0.007 (3)
N40.043 (3)0.051 (3)0.063 (3)0.001 (2)−0.003 (2)−0.002 (2)
O10.050 (3)0.066 (3)0.088 (4)0.002 (2)−0.002 (2)0.004 (2)
O20.081 (3)0.065 (3)0.130 (5)−0.015 (3)−0.021 (3)0.023 (3)
O30.060 (3)0.075 (3)0.140 (5)−0.015 (3)0.007 (3)−0.005 (3)
O40.080 (3)0.082 (3)0.076 (4)−0.001 (3)−0.008 (3)−0.005 (3)
O50.0933 (17)0.0914 (17)0.0919 (18)−0.0022 (10)−0.0005 (10)0.0002 (10)
O60.096 (4)0.110 (5)0.130 (5)0.002 (4)−0.022 (4)−0.021 (4)
O70.052 (2)0.051 (2)0.080 (3)−0.003 (2)−0.005 (2)0.010 (2)
O80.069 (3)0.084 (3)0.094 (4)−0.003 (3)−0.004 (3)0.032 (3)
O90.057 (3)0.074 (3)0.111 (4)−0.007 (2)0.010 (3)0.013 (3)
O100.062 (3)0.050 (3)0.075 (3)−0.005 (2)0.004 (2)−0.011 (2)
O110.098 (4)0.048 (3)0.081 (4)−0.007 (2)0.011 (3)−0.003 (3)
O120.136 (5)0.051 (3)0.086 (4)0.011 (3)0.001 (3)−0.002 (3)
O130.092 (3)0.080 (3)0.076 (3)−0.011 (3)−0.009 (3)0.005 (3)
O140.095 (4)0.115 (4)0.091 (4)−0.005 (3)−0.001 (3)−0.003 (3)
O150.45 (2)0.300 (17)0.37 (2)−0.042 (16)−0.035 (16)−0.220 (17)
C10.059 (4)0.051 (4)0.080 (5)−0.005 (3)0.005 (4)−0.017 (3)
C20.068 (4)0.079 (5)0.097 (5)0.001 (4)−0.007 (4)−0.011 (4)
C30.070 (5)0.098 (5)0.112 (6)0.020 (4)−0.014 (4)−0.019 (5)
C40.062 (5)0.097 (6)0.139 (7)−0.003 (4)0.000 (5)−0.020 (5)
C50.057 (4)0.053 (4)0.091 (5)−0.005 (3)−0.007 (4)−0.015 (4)
C60.053 (4)0.051 (4)0.133 (6)−0.006 (3)0.005 (4)−0.028 (5)
C70.074 (5)0.094 (5)0.105 (6)0.006 (4)−0.003 (5)−0.008 (5)
C80.085 (5)0.119 (7)0.134 (7)−0.001 (5)−0.010 (5)−0.071 (6)
C90.098 (6)0.063 (5)0.183 (8)−0.004 (4)0.002 (6)−0.026 (6)
C100.051 (4)0.069 (4)0.093 (5)0.002 (3)−0.005 (4)0.014 (4)
C110.059 (4)0.060 (4)0.078 (4)0.006 (3)−0.004 (3)−0.004 (3)
C120.054 (4)0.075 (4)0.076 (4)0.013 (3)−0.005 (3)−0.006 (4)
C130.057 (4)0.080 (4)0.066 (4)−0.006 (3)−0.004 (3)0.003 (3)
C140.057 (3)0.065 (4)0.051 (4)−0.006 (3)0.000 (3)0.005 (3)
C150.070 (4)0.069 (4)0.067 (4)−0.020 (3)−0.002 (3)0.004 (3)
C160.084 (4)0.053 (3)0.072 (4)−0.013 (3)0.003 (4)−0.006 (3)
C170.072 (4)0.050 (3)0.059 (4)−0.001 (3)0.004 (3)0.002 (3)
C180.086 (4)0.053 (4)0.081 (4)0.000 (3)0.001 (4)−0.005 (3)
C190.087 (5)0.059 (4)0.086 (5)0.022 (4)0.004 (4)−0.002 (4)
C200.064 (4)0.064 (4)0.079 (4)0.007 (3)0.002 (3)−0.004 (3)
C210.057 (3)0.047 (3)0.046 (3)−0.002 (3)0.002 (3)0.004 (3)
C220.055 (3)0.048 (3)0.044 (3)0.000 (3)−0.001 (3)0.002 (3)
C230.052 (4)0.053 (4)0.068 (4)−0.001 (3)0.002 (3)−0.008 (3)
C240.064 (4)0.073 (4)0.075 (5)0.000 (3)−0.008 (4)−0.004 (4)
C250.068 (4)0.093 (5)0.086 (5)0.015 (4)−0.018 (4)−0.007 (4)
C260.051 (4)0.090 (5)0.111 (6)0.000 (4)−0.008 (4)−0.014 (5)
C270.060 (4)0.039 (3)0.075 (5)−0.003 (3)0.004 (3)−0.001 (3)
C280.042 (3)0.045 (3)0.073 (4)−0.001 (3)0.001 (3)−0.004 (3)
C290.057 (4)0.057 (4)0.074 (5)−0.004 (3)0.002 (3)−0.010 (3)
C300.088 (5)0.058 (4)0.096 (5)0.005 (4)0.005 (4)−0.019 (4)
C310.125 (6)0.049 (4)0.107 (6)0.010 (4)0.007 (5)−0.003 (4)
C320.047 (3)0.048 (4)0.076 (5)−0.005 (3)0.004 (3)−0.010 (3)
C330.058 (4)0.062 (4)0.091 (5)0.000 (3)0.002 (4)−0.010 (3)
C340.052 (4)0.081 (4)0.094 (5)0.016 (3)0.001 (4)−0.010 (4)
C350.049 (3)0.087 (4)0.074 (4)0.002 (3)0.001 (3)0.001 (4)
C360.061 (4)0.069 (4)0.054 (4)−0.011 (3)−0.001 (3)0.001 (3)
C370.056 (4)0.077 (4)0.076 (4)−0.019 (3)−0.004 (3)0.006 (3)
C380.073 (4)0.064 (4)0.077 (4)−0.023 (3)0.001 (3)0.001 (3)
C390.063 (4)0.056 (3)0.056 (4)−0.011 (3)0.004 (3)0.006 (3)
C400.075 (4)0.051 (3)0.069 (4)−0.004 (3)−0.003 (3)0.001 (3)
C410.073 (4)0.058 (4)0.073 (4)0.012 (3)0.001 (4)0.006 (3)
C420.053 (3)0.058 (4)0.073 (4)0.004 (3)−0.004 (3)0.001 (3)
C430.055 (3)0.053 (3)0.048 (3)−0.003 (3)−0.003 (3)0.000 (3)
C440.049 (3)0.058 (3)0.049 (3)−0.009 (3)0.000 (3)0.000 (3)
C450.199 (14)0.35 (2)0.097 (10)−0.035 (15)−0.029 (9)0.080 (12)

Geometric parameters (Å, °)

Cu1—O11.935 (4)C12—C131.340 (8)
Cu1—N12.008 (5)C12—H120.9300
Cu1—O42.012 (5)C13—C141.412 (9)
Cu1—N22.017 (5)C13—H130.9300
Cu1—O132.249 (5)C14—C221.400 (8)
Cu2—O71.944 (4)C14—C151.420 (8)
Cu2—O101.947 (4)C15—C161.335 (9)
Cu2—N32.015 (5)C15—H15A0.9300
Cu2—N42.016 (5)C16—C171.432 (9)
Cu2—O142.248 (5)C16—H160.9300
N1—C111.321 (7)C17—C211.390 (8)
N1—C221.360 (7)C17—C181.410 (9)
N2—C201.329 (7)C18—C191.343 (9)
N2—C211.367 (7)C18—H180.9300
N3—C331.299 (7)C19—C201.399 (9)
N3—C441.350 (7)C19—H190.9300
N4—C421.333 (7)C20—H200.9300
N4—C431.359 (7)C21—C221.417 (8)
O1—C51.286 (8)C23—C241.335 (8)
O2—C51.214 (8)C23—C271.480 (8)
O3—C41.349 (9)C24—C251.445 (9)
O3—C11.377 (7)C24—H240.9300
O4—C101.196 (8)C25—C261.312 (10)
O5—C101.249 (8)C25—H250.9300
O6—C61.354 (9)C26—H260.9300
O6—C91.379 (11)C28—C291.339 (8)
O7—C271.283 (7)C28—C321.478 (8)
O8—C271.228 (7)C29—C301.415 (9)
O9—C261.359 (8)C29—H290.9300
O9—C231.371 (7)C30—C311.313 (10)
O10—C321.277 (7)C30—H300.9300
O11—C321.233 (7)C31—H310.9300
O12—C311.358 (8)C33—C341.395 (9)
O12—C281.360 (7)C33—H330.9300
O13—H13A0.8500C34—C351.340 (9)
O13—H13B0.8501C34—H340.9300
O14—H14A0.8519C35—C361.409 (9)
O14—H14B0.8500C35—H350.9300
O15—C451.301 (9)C36—C441.401 (8)
O15—H150.8200C36—C371.424 (9)
C1—C21.320 (9)C37—C381.342 (9)
C1—C51.488 (9)C37—H370.9300
C2—C31.451 (10)C38—C391.435 (8)
C2—H20.9300C38—H380.9300
C3—C41.319 (11)C39—C401.400 (8)
C3—H30.9300C39—C431.407 (8)
C4—H40.9300C40—C411.348 (9)
C6—C71.257 (10)C40—H400.9300
C6—C101.537 (10)C41—C421.407 (8)
C7—C81.329 (10)C41—H410.9300
C7—H70.9300C42—H420.9300
C8—C91.309 (12)C43—C441.432 (8)
C8—H80.9300C45—H45A0.9600
C9—H90.9300C45—H45B0.9600
C11—C121.393 (8)C45—H45C0.9600
C11—H110.9300
O1—Cu1—N1169.33 (19)C15—C16—H16119.3
O1—Cu1—O494.15 (18)C17—C16—H16119.4
N1—Cu1—O493.28 (19)C21—C17—C18116.5 (6)
O1—Cu1—N289.53 (18)C21—C17—C16118.5 (6)
N1—Cu1—N281.21 (19)C18—C17—C16125.1 (6)
O4—Cu1—N2163.4 (2)C19—C18—C17119.7 (6)
O1—Cu1—O1396.10 (18)C19—C18—H18120.2
N1—Cu1—O1391.95 (18)C17—C18—H18120.1
O4—Cu1—O1386.9 (2)C18—C19—C20120.9 (7)
N2—Cu1—O13108.89 (18)C18—C19—H19119.7
O7—Cu2—O1095.21 (16)C20—C19—H19119.4
O7—Cu2—N3170.34 (19)N2—C20—C19121.3 (6)
O10—Cu2—N391.23 (18)N2—C20—H20119.2
O7—Cu2—N491.33 (17)C19—C20—H20119.5
O10—Cu2—N4170.05 (19)N2—C21—C17123.7 (6)
N3—Cu2—N481.39 (18)N2—C21—C22116.0 (5)
O7—Cu2—O1492.35 (18)C17—C21—C22120.4 (6)
O10—Cu2—O1496.00 (19)N1—C22—C14123.8 (5)
N3—Cu2—O1494.1 (2)N1—C22—C21116.4 (5)
N4—Cu2—O1491.20 (19)C14—C22—C21119.8 (5)
C11—N1—C22116.9 (5)C24—C23—O9110.2 (6)
C11—N1—Cu1129.7 (4)C24—C23—C27133.2 (6)
C22—N1—Cu1113.4 (4)O9—C23—C27116.7 (6)
C20—N2—C21118.0 (5)C23—C24—C25106.0 (6)
C20—N2—Cu1129.0 (4)C23—C24—H24127.1
C21—N2—Cu1113.0 (4)C25—C24—H24126.8
C33—N3—C44116.1 (5)C26—C25—C24106.2 (7)
C33—N3—Cu2130.4 (4)C26—C25—H25126.7
C44—N3—Cu2113.5 (4)C24—C25—H25127.1
C42—N4—C43118.1 (5)C25—C26—O9111.5 (7)
C42—N4—Cu2129.1 (4)C25—C26—H26124.4
C43—N4—Cu2112.6 (4)O9—C26—H26124.1
C5—O1—Cu1125.1 (4)O8—C27—O7127.3 (6)
C4—O3—C1104.9 (6)O8—C27—C23118.5 (6)
C10—O4—Cu1107.2 (5)O7—C27—C23114.2 (6)
C6—O6—C9104.3 (8)C29—C28—O12111.1 (5)
C27—O7—Cu2122.0 (4)C29—C28—C32130.6 (6)
C26—O9—C23106.0 (6)O12—C28—C32118.3 (6)
C32—O10—Cu2111.5 (4)C28—C29—C30106.0 (6)
C31—O12—C28104.4 (6)C28—C29—H29127.2
Cu1—O13—H13A87.5C30—C29—H29126.8
Cu1—O13—H13B130.1C31—C30—C29106.0 (7)
H13A—O13—H13B104.9C31—C30—H30127.0
Cu2—O14—H14A77.5C29—C30—H30127.0
Cu2—O14—H14B150.6C30—C31—O12112.5 (7)
H14A—O14—H14B105.5C30—C31—H31123.8
C45—O15—H15108.8O12—C31—H31123.7
C2—C1—O3111.5 (6)O11—C32—O10123.7 (6)
C2—C1—C5133.2 (7)O11—C32—C28120.1 (7)
O3—C1—C5115.1 (6)O10—C32—C28116.2 (6)
C1—C2—C3105.6 (7)N3—C33—C34125.4 (6)
C1—C2—H2127.3N3—C33—H33117.9
C3—C2—H2127.1C34—C33—H33116.6
C4—C3—C2105.6 (7)C35—C34—C33118.1 (6)
C4—C3—H3127.3C35—C34—H34120.1
C2—C3—H3127.1C33—C34—H34121.9
C3—C4—O3112.4 (8)C34—C35—C36120.2 (6)
C3—C4—H4123.6C34—C35—H35120.0
O3—C4—H4124.0C36—C35—H35119.8
O2—C5—O1127.4 (6)C44—C36—C35116.3 (6)
O2—C5—C1119.7 (7)C44—C36—C37118.2 (6)
O1—C5—C1112.9 (7)C35—C36—C37125.5 (6)
C7—C6—O6107.8 (7)C38—C37—C36121.9 (6)
C7—C6—C10138.6 (9)C38—C37—H37119.0
O6—C6—C10113.3 (8)C36—C37—H37119.1
C6—C7—C8113.3 (9)C37—C38—C39121.6 (6)
C6—C7—H7122.0C37—C38—H38119.1
C8—C7—H7124.5C39—C38—H38119.2
C9—C8—C7104.5 (9)C40—C39—C43116.8 (6)
C9—C8—H8127.5C40—C39—C38125.5 (6)
C7—C8—H8128.0C43—C39—C38117.8 (6)
C8—C9—O6109.9 (8)C41—C40—C39120.1 (6)
C8—C9—H9124.3C41—C40—H40119.9
O6—C9—H9125.8C39—C40—H40119.9
O4—C10—O5125.9 (8)C40—C41—C42120.1 (6)
O4—C10—C6121.1 (7)C40—C41—H41120.0
O5—C10—C6113.0 (8)C42—C41—H41119.9
N1—C11—C12123.6 (6)N4—C42—C41121.6 (6)
N1—C11—H11118.3N4—C42—H42119.1
C12—C11—H11118.2C41—C42—H42119.2
C13—C12—C11119.3 (6)N4—C43—C39123.2 (5)
C13—C12—H12120.1N4—C43—C44116.6 (5)
C11—C12—H12120.6C39—C43—C44120.2 (5)
C12—C13—C14120.5 (6)N3—C44—C36123.9 (6)
C12—C13—H13119.9N3—C44—C43115.8 (5)
C14—C13—H13119.7C36—C44—C43120.3 (6)
C22—C14—C13116.0 (6)O15—C45—H45A108.1
C22—C14—C15118.8 (6)O15—C45—H45B104.1
C13—C14—C15125.2 (6)H45A—C45—H45B109.5
C16—C15—C14121.2 (6)O15—C45—H45C116.0
C16—C15—H15A119.4H45A—C45—H45C109.5
C14—C15—H15A119.3H45B—C45—H45C109.5
C15—C16—C17121.3 (6)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O14—H14B···O5i0.851.762.611 (8)177
O14—H14A···O80.852.072.634 (7)124
O13—H13B···O110.851.962.749 (7)154
O13—H13A···O20.851.872.708 (7)169
O15—H15···O40.821.862.474 (17)131

Symmetry codes: (i) x, y, z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV2568).

References

  • Ai, C.-C., Xiang, J.-F., Li, M. & Yuan, L.-J. (2007). Acta Cryst. E63, m565–m566.
  • Li, X.-F., An, Y. & Yin, Y.-S. (2007). Acta Cryst. E63, m3117–m3118.
  • Rodrigues, B. L. (2004). Acta Cryst. E60, m1169–m1171.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Siemens (1996). SMART and SAINT Siemens Analytical X-ray Systems, Inc., Madison, Wisconsin, USA.

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