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

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ISSN: 2056-9890

Aqua­(furan-2-carboxyl­ato-κO)(furan-2-carboxyl­ato-κ2O,O′)(1,10-phenanthroline-κ2N,N′)copper(II) methanol hemisolvate

aDepartment of Materials and Chemical Engineering, Taishan University, 271021 Taian, Shandong, People's Republic of China
*Correspondence e-mail: xiangyz_2008@163.com

(Received 24 May 2009; accepted 24 June 2009; online 1 July 2009)

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 ππ 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[Ai, C.-C., Xiang, J.-F., Li, M. & Yuan, L.-J. (2007). Acta Cryst. E63, m565-m566.]); Li et al. (2007[Li, X.-F., An, Y. & Yin, Y.-S. (2007). Acta Cryst. E63, m3117-m3118.]); Rodrigues (2004[Rodrigues, B. L. (2004). Acta Cryst. E60, m1169-m1171.]).

[Scheme 1]

Experimental

Crystal data
  • [Cu(C5H3O3)2(C12H8N2)2(H2O)]·0.5CH4O

  • Mr = 499.93

  • Tetragonal, I 41 /a

  • 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.750, Tmax = 0.836

  • 43834 measured reflections

  • 7448 independent reflections

  • 4004 reflections with I > 2σ(I)

  • Rint = 0.100

Refinement
  • R[F2 > 2σ(F2)] = 0.055

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O14—H14B⋯O5i 0.85 1.76 2.611 (8) 177
O14—H14A⋯O8 0.85 2.07 2.634 (7) 124
O13—H13B⋯O11 0.85 1.96 2.749 (7) 154
O13—H13A⋯O2 0.85 1.87 2.708 (7) 169
O15—H15⋯O4 0.82 1.86 2.474 (17) 131
Symmetry code: (i) x, y, z+1.

Data collection: SMART (Siemens, 1996[Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Systems, Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Siemens, 1996[Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Systems, 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

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.

Related literature top

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

Experimental top

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 top

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).

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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 content of asymmetric unit of the title compound, with atomic numbering and 30% probability displacement ellipsoids.
Aqua(furan-2-carboxylato-κO)(furan-2-carboxylato- κ2O,O')(1,10-phenanthroline-κ2N,N')copper(II) methanol hemisolvate top
Crystal data top
[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 top
Bruker SMART APEX
diffractometer
7448 independent reflections
Radiation source: fine-focus sealed tube4004 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.100
ϕ and ω scansθmax = 25.1°, θmin = 1.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 2440
Tmin = 0.750, Tmax = 0.836k = 4040
43834 measured reflectionsl = 1717
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)] = 0.055Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.169H-atom parameters constrained
S = 0.97 w = 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
Crystal data top
[Cu(C5H3O3)2(C12H8N2)(H2O)]·0.5CH4OZ = 32
Mr = 499.93Mo Kα radiation
Tetragonal, I41/aµ = 1.09 mm1
a = 34.129 (17) ÅT = 273 K
c = 14.450 (6) Å0.28 × 0.22 × 0.17 mm
V = 16831 (14) Å3
Data collection top
Bruker SMART APEX
diffractometer
7448 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
4004 reflections with I > 2σ(I)
Tmin = 0.750, Tmax = 0.836Rint = 0.100
43834 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.055792 restraints
wR(F2) = 0.169H-atom parameters constrained
S = 0.97 w = 1/[σ2(Fo2) + (0.0667P)2 + 46.5236P]
where P = (Fo2 + 2Fc2)/3
7448 reflectionsΔρmax = 0.60 e Å3
595 parametersΔρmin = 0.54 e Å3
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
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)
H80.43020.78450.03320.135*
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) top
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, º) top
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, º) top
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 code: (i) x, y, z+1.

Experimental details

Crystal data
Chemical formula[Cu(C5H3O3)2(C12H8N2)(H2O)]·0.5CH4O
Mr499.93
Crystal system, space groupTetragonal, I41/a
Temperature (K)273
a, c (Å)34.129 (17), 14.450 (6)
V3)16831 (14)
Z32
Radiation typeMo Kα
µ (mm1)1.09
Crystal size (mm)0.28 × 0.22 × 0.17
Data collection
DiffractometerBruker SMART APEX
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.750, 0.836
No. of measured, independent and
observed [I > 2σ(I)] reflections
43834, 7448, 4004
Rint0.100
(sin θ/λ)max1)0.596
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.055, 0.169, 0.97
No. of reflections7448
No. of parameters595
No. of restraints792
H-atom treatmentH-atom parameters constrained
w = 1/[σ2(Fo2) + (0.0667P)2 + 46.5236P]
where P = (Fo2 + 2Fc2)/3
Δρmax, Δρmin (e Å3)0.60, 0.54

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O14—H14B···O5i0.851.762.611 (8)177.0
O14—H14A···O80.852.072.634 (7)123.5
O13—H13B···O110.851.962.749 (7)154.1
O13—H13A···O20.851.872.708 (7)168.7
O15—H15···O40.821.862.474 (17)131.1
Symmetry code: (i) x, y, z+1.
 

Acknowledgements

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

References

First citationAi, C.-C., Xiang, J.-F., Li, M. & Yuan, L.-J. (2007). Acta Cryst. E63, m565–m566.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationLi, X.-F., An, Y. & Yin, Y.-S. (2007). Acta Cryst. E63, m3117–m3118.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationRodrigues, B. L. (2004). Acta Cryst. E60, m1169–m1171.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (1996). 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
First citationSiemens (1996). SMART and SAINT. Siemens Analytical X-ray Systems, Inc., Madison, Wisconsin, USA.  Google Scholar

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