supplementary materials


HTML versionpdf versioncif file3d viewstructure factorssupplementary materialsCIF check reportsimilar papers buy article online

Acta Cryst. (2007). E63, m2184    [ doi:10.1107/S1600536807034678 ]

(2,2'-Dicarboxy-4,4'-carbonyldibenzoato)bis(1,10-phenanthroline)copper(II) dihydrate

L.-J. Hao and T.-L. Yu

Abstract top

In the title compound, [Cu(C17H8O9)(C12H8N2)2]·2H2O, the CuII cation is hexacoordinated by two carboxylate O atoms from one of the two deprotonated carboxyl groups in the 3,3,4,4-benzophenone tetracarboxylate, and four N atoms from two 1,10-phenanthrolines, showing a slightly distorted octahedral geometry. A network of hydrogen bonds links the units into a three-dimensional structure.

Comment top

In recent years, carboxylic acids have been widely used as polydentate ligands that can coordinate to transition or rare earth ions, yielding complexes with interesting properties that are useful in materials science (Church & Halvorson, 1959; Chung et al., 1971) and in biological systems (Okabe & Oya, 2000; Serre et al., 2005; Pocker & Fong, 1980; Scapin et al., 1997). For example, Kim et al. (2001) focused on the syntheses of transition metal complexes containing benzene carboxylate and rigid aromatic pyridine ligands in order to study their electronic conductivity and magnetic properties. The importance of transition metal dicarboxylate complexes motivated us to pursue synthetic strategies for these compounds, using 3,3,4,4-benzophenone tetracarboxylate as a polydentate ligand. Here we report the synthesis and X-ray crystal structure analysis of the title compound.

The molecular structure of the title compound is shown in Fig. 1. The Cu(II) ion is hexa-coordinated, with two carboxylate oxygen atoms from the 3,3,4,4-benzophenone tetracarboxylate and four nitrogen atoms from two 1,10-phenanthrolines, showing a slightly distorted octahedral geometry. The Cu—O bond and Cu—N distances are in the ranges 2.378 (2)–2.0837 (19) and 2.114 (3)–2.179 (3) Å, respectively.

Related literature top

For uses of carboxylic acids in materials science, see: Church & Halvorson (1959). For uses in biological systems, see: Chung et al. (1971); Okabe & Oya (2000); Serre et al. (2005); Pocker & Fong (1980); Scapin et al. (1997); Kim et al. (2001).

Experimental top

A mixture of copper acetate (0.5 mmol, 0.149 g), 3,3,4,4-benzophenone tetracarboxylic acid (0.5 mmol, 0.162 g), and 1,10-phenanthroline (0.5 mmol, 0.10 g) in 20 ml of a 1:1 solution of water and ethanol was sealed in a 30 ml Teflon-lined stainless steel autoclave, and kept at 150 °C for 2 days. Green, block-shaped crystals were obtained at a yield of 20% after slowly cooling to room temperature. Anal. Calc. for C41H28CuN4O11: C 60.28, H 3.43, N 6.86, Cu 7.84%; Found: C 60.33, H 3.49, N 6.81, Cu 7.80%.

Refinement top

The H atoms of the water molecule were located from difference density maps and were refined with distance restraints of d(H–H) = 1.38 (2) Å, d(O—H) = 0.88 (2) Å, and with a fixed Uiso of 0.80 Å2. All other H atoms were placed in calculated positions with a C—H bond distance of 0.93 Å and Uiso(H) = 1.2Ueq of the carrier atom.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. A view of the the title compound, showing the atomic numbering scheme and 30% probability displacement ellipsoids.
(2,2'-Dicarboxy-4,4'-carbonyldibenzoato)bis(1,10-phenanthroline)copper(II) dihydrate top
Crystal data top
[Cu(C17H8O9)(C12H8N2)2]·2H2OF(000) = 1676
Mr = 816.21Dx = 1.523 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 6912 reflections
a = 14.3011 (9) Åθ = 1.5–26.0°
b = 16.9401 (10) ŵ = 0.69 mm−1
c = 14.9839 (9) ÅT = 293 K
β = 101.371 (1)°Block, green
V = 3558.8 (4) Å30.15 × 0.15 × 0.15 mm
Z = 4
Data collection top
Bruker APEXII CCD area-detector
diffractometer		6912 independent reflections
Radiation source: fine-focus sealed tube3976 reflections with I > 2σ(I)
graphiteRint = 0.061
φ and ω scansθmax = 26.0°, θmin = 1.5°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)		h = −16→17
Tmin = 0.904, Tmax = 0.904k = −20→20
17576 measured reflectionsl = −9→17
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.127 w = 1/[σ2(Fo2) + (0.0662P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max < 0.001
6912 reflectionsΔρmax = 0.86 e Å−3
528 parametersΔρmin = −0.84 e Å−3
6 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997)
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.00
Crystal data top
[Cu(C17H8O9)(C12H8N2)2]·2H2OV = 3558.8 (4) Å3
Mr = 816.21Z = 4
Monoclinic, P21/cMo Kα radiation
a = 14.3011 (9) ŵ = 0.69 mm−1
b = 16.9401 (10) ÅT = 293 K
c = 14.9839 (9) Å0.15 × 0.15 × 0.15 mm
β = 101.371 (1)°
Data collection top
Bruker APEXII CCD area-detector
diffractometer		6912 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2001)		3976 reflections with I > 2σ(I)
Tmin = 0.904, Tmax = 0.904Rint = 0.061
17576 measured reflectionsθmax = 26.0°
Refinement top
R[F2 > 2σ(F2)] = 0.044H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.127Δρmax = 0.86 e Å−3
S = 1.00Δρmin = −0.84 e Å−3
6912 reflectionsAbsolute structure: ?
528 parametersFlack parameter: ?
6 restraintsRogers parameter: ?
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
C10.8370 (3)0.4926 (3)0.2632 (3)0.0593 (11)
H10.79170.45260.25100.071*
C20.9332 (3)0.4719 (3)0.2790 (3)0.0715 (13)
H20.95090.41930.27710.086*
C31.0000 (3)0.5284 (3)0.2971 (3)0.0723 (13)
H31.06420.51480.30620.087*
C40.9735 (3)0.6076 (3)0.3024 (3)0.0625 (12)
C51.0388 (3)0.6732 (3)0.3252 (3)0.0756 (14)
H51.10400.66350.33790.091*
C61.0082 (3)0.7460 (3)0.3285 (3)0.0752 (14)
H61.05250.78650.34260.090*
C70.9086 (3)0.7648 (3)0.3108 (3)0.0588 (11)
C80.8728 (3)0.8412 (3)0.3158 (3)0.0691 (12)
H80.91440.88360.32950.083*
C90.7774 (3)0.8531 (3)0.3006 (3)0.0644 (12)
H90.75290.90350.30490.077*
C100.7162 (3)0.7889 (2)0.2785 (3)0.0573 (11)
H100.65080.79800.26770.069*
C110.8423 (2)0.7034 (2)0.2890 (3)0.0486 (10)
C120.8751 (2)0.6237 (2)0.2842 (3)0.0497 (10)
C130.4743 (3)0.7042 (3)0.2495 (3)0.0657 (12)
H130.50020.71280.31070.079*
C140.3821 (3)0.7304 (3)0.2149 (4)0.0725 (13)
H140.34690.75490.25310.087*
C150.3435 (3)0.7201 (2)0.1253 (3)0.0622 (12)
H150.28260.73880.10140.075*
C160.3957 (2)0.6813 (2)0.0699 (3)0.0490 (10)
C170.3613 (3)0.6667 (2)−0.0247 (3)0.0604 (12)
H170.30080.6841−0.05200.072*
C180.4146 (3)0.6282 (2)−0.0746 (3)0.0573 (11)
H180.38990.6187−0.13590.069*
C190.5088 (3)0.6014 (2)−0.0358 (3)0.0479 (9)
C200.5678 (3)0.5606 (2)−0.0853 (3)0.0567 (11)
H200.54660.5503−0.14690.068*
C210.6558 (3)0.5365 (2)−0.0428 (3)0.0584 (11)
H210.69480.5087−0.07460.070*
C220.6866 (3)0.5537 (2)0.0485 (3)0.0523 (10)
H220.74750.53740.07660.063*
C230.5450 (2)0.6154 (2)0.0557 (3)0.0390 (8)
C240.4882 (2)0.6564 (2)0.1100 (3)0.0418 (9)
C250.5931 (2)0.5078 (2)0.3286 (3)0.0412 (9)
C260.5346 (2)0.45871 (19)0.3815 (2)0.0358 (8)
C270.5710 (2)0.40717 (19)0.4523 (2)0.0367 (8)
C280.6751 (2)0.3964 (2)0.4895 (3)0.0428 (9)
C290.5087 (2)0.3617 (2)0.4913 (2)0.0377 (8)
H290.53350.32740.53860.045*
C300.4100 (2)0.36606 (19)0.4614 (2)0.0339 (8)
C310.3744 (2)0.4195 (2)0.3933 (2)0.0392 (9)
H310.30880.42470.37400.047*
C320.4356 (2)0.4653 (2)0.3536 (2)0.0427 (9)
H320.41040.50080.30790.051*
C330.3490 (2)0.3106 (2)0.5019 (2)0.0361 (8)
C340.2422 (2)0.31950 (19)0.4831 (2)0.0360 (8)
C350.1875 (2)0.2517 (2)0.4652 (2)0.0410 (9)
H350.21850.20390.46170.049*
C360.0881 (2)0.2516 (2)0.4520 (3)0.0433 (9)
C370.0438 (3)0.1704 (2)0.4357 (3)0.0600 (12)
C380.0422 (2)0.3247 (2)0.4594 (3)0.0392 (8)
C39−0.0641 (2)0.3395 (2)0.4486 (3)0.0541 (11)
C400.0981 (2)0.3921 (2)0.4798 (3)0.0411 (9)
H400.06810.43980.48660.049*
C410.1964 (2)0.39093 (19)0.4903 (3)0.0385 (8)
H410.23130.43740.50190.046*
Cu10.66501 (3)0.61130 (3)0.23968 (3)0.04183 (16)
N10.8075 (2)0.5662 (2)0.2648 (2)0.0497 (8)
N20.7463 (2)0.71606 (18)0.2723 (2)0.0472 (8)
N30.5263 (2)0.66769 (19)0.1986 (2)0.0494 (8)
N40.63421 (19)0.59196 (16)0.0981 (2)0.0451 (8)
O10.62329 (16)0.57379 (14)0.35849 (17)0.0443 (6)
O20.60284 (18)0.48301 (17)0.25289 (18)0.0618 (8)
O30.72864 (16)0.42358 (16)0.4347 (2)0.0560 (7)
H3A0.78320.40690.45080.084*
O40.70660 (18)0.3663 (2)0.5624 (2)0.0740 (8)
O50.38447 (16)0.25576 (14)0.54750 (18)0.0476 (5)
O60.0945 (2)0.11279 (17)0.4451 (3)0.0797 (9)
O7−0.04731 (19)0.16318 (18)0.4096 (3)0.0849 (9)
H7−0.07190.20710.40390.153*
O8−0.12265 (18)0.28825 (19)0.4100 (3)0.1021 (12)
O9−0.09096 (16)0.40276 (15)0.4745 (2)0.0529 (6)
O100.7694 (4)0.4462 (5)0.7582 (5)0.072 (3)
O110.1075 (10)0.9558 (9)0.4964 (13)0.071 (3)
H1W0.7161 (12)0.443 (3)0.771 (3)0.080*
H2W0.8127 (19)0.447 (4)0.8053 (19)0.080*
H3W0.096 (3)0.933 (4)0.4435 (16)0.080*
H4W0.158 (2)0.980 (3)0.516 (2)0.080*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.055 (2)0.065 (3)0.062 (3)0.012 (2)0.022 (2)0.010 (2)
C20.064 (3)0.074 (3)0.083 (4)0.024 (2)0.030 (3)0.017 (3)
C30.045 (2)0.102 (4)0.074 (3)0.022 (2)0.021 (2)0.019 (3)
C40.040 (2)0.090 (3)0.059 (3)0.009 (2)0.015 (2)0.017 (3)
C50.034 (2)0.119 (4)0.075 (4)−0.007 (3)0.012 (2)0.014 (3)
C60.052 (3)0.092 (4)0.085 (4)−0.015 (3)0.020 (3)0.006 (3)
C70.050 (2)0.076 (3)0.051 (3)−0.010 (2)0.011 (2)0.011 (2)
C80.076 (3)0.070 (3)0.062 (3)−0.017 (3)0.014 (3)0.005 (2)
C90.075 (3)0.058 (3)0.060 (3)−0.002 (2)0.014 (2)0.006 (2)
C100.058 (2)0.064 (3)0.052 (3)0.007 (2)0.013 (2)0.014 (2)
C110.040 (2)0.067 (3)0.040 (2)−0.0021 (18)0.0122 (18)0.011 (2)
C120.0363 (19)0.068 (3)0.048 (3)0.0039 (18)0.0166 (18)0.013 (2)
C130.050 (2)0.093 (3)0.057 (3)0.015 (2)0.017 (2)−0.007 (3)
C140.052 (3)0.091 (3)0.075 (4)0.017 (2)0.015 (3)−0.014 (3)
C150.043 (2)0.065 (3)0.073 (3)0.011 (2)0.001 (2)0.002 (3)
C160.041 (2)0.046 (2)0.057 (3)0.0018 (17)0.002 (2)0.007 (2)
C170.046 (2)0.059 (3)0.066 (3)−0.002 (2)−0.014 (2)0.006 (2)
C180.061 (3)0.056 (3)0.048 (3)−0.009 (2)−0.005 (2)0.003 (2)
C190.057 (2)0.041 (2)0.046 (3)−0.0150 (18)0.011 (2)0.0048 (19)
C200.075 (3)0.051 (2)0.048 (3)−0.018 (2)0.020 (2)−0.006 (2)
C210.067 (3)0.058 (3)0.058 (3)−0.010 (2)0.031 (2)−0.008 (2)
C220.045 (2)0.055 (2)0.062 (3)−0.0040 (18)0.022 (2)0.002 (2)
C230.0411 (19)0.0355 (18)0.040 (2)−0.0067 (15)0.0076 (17)0.0052 (17)
C240.0393 (19)0.039 (2)0.046 (3)−0.0018 (16)0.0061 (18)0.0069 (18)
C250.0253 (17)0.055 (2)0.043 (2)0.0009 (16)0.0065 (16)0.000 (2)
C260.0303 (17)0.044 (2)0.035 (2)−0.0038 (15)0.0109 (15)−0.0096 (17)
C270.0267 (16)0.043 (2)0.042 (2)0.0000 (14)0.0091 (16)−0.0068 (17)
C280.0290 (17)0.047 (2)0.053 (3)0.0011 (16)0.0092 (18)0.003 (2)
C290.0290 (17)0.0428 (19)0.041 (2)0.0045 (14)0.0071 (16)0.0004 (17)
C300.0245 (15)0.0402 (19)0.038 (2)0.0002 (14)0.0091 (15)−0.0085 (17)
C310.0231 (16)0.050 (2)0.043 (2)0.0017 (15)0.0019 (15)−0.0027 (19)
C320.0320 (18)0.054 (2)0.042 (2)0.0042 (16)0.0065 (17)0.0023 (18)
C330.0315 (17)0.0329 (19)0.044 (2)0.0052 (15)0.0080 (16)−0.0049 (17)
C340.0258 (16)0.043 (2)0.042 (2)−0.0015 (14)0.0128 (15)0.0025 (17)
C350.0352 (19)0.039 (2)0.053 (2)0.0023 (15)0.0181 (18)−0.0023 (18)
C360.0333 (18)0.043 (2)0.055 (3)−0.0053 (15)0.0130 (18)−0.0004 (19)
C370.044 (2)0.051 (3)0.090 (4)−0.012 (2)0.025 (2)−0.007 (2)
C380.0257 (16)0.043 (2)0.049 (2)−0.0027 (15)0.0073 (16)0.0004 (18)
C390.0286 (19)0.055 (3)0.079 (3)−0.0022 (18)0.013 (2)0.004 (2)
C400.0273 (16)0.042 (2)0.054 (2)0.0053 (15)0.0098 (16)0.0020 (18)
C410.0265 (16)0.0373 (19)0.052 (2)−0.0009 (14)0.0095 (16)−0.0010 (18)
Cu10.0311 (2)0.0549 (3)0.0406 (3)0.0029 (2)0.00990 (19)0.0077 (2)
N10.0458 (18)0.058 (2)0.048 (2)0.0079 (16)0.0166 (16)0.0102 (17)
N20.0412 (17)0.057 (2)0.044 (2)0.0050 (15)0.0109 (15)0.0135 (16)
N30.0429 (17)0.064 (2)0.041 (2)0.0053 (15)0.0077 (16)−0.0010 (17)
N40.0384 (16)0.0452 (18)0.055 (2)−0.0019 (13)0.0172 (15)0.0076 (15)
O10.0424 (13)0.0413 (14)0.0509 (17)−0.0039 (11)0.0135 (12)−0.0007 (13)
O20.0624 (17)0.087 (2)0.0431 (17)−0.0233 (15)0.0275 (14)−0.0160 (16)
O30.0252 (12)0.0642 (17)0.081 (2)0.0072 (12)0.0155 (14)0.0142 (15)
O40.0324 (13)0.119 (2)0.0676 (17)0.0069 (14)0.0020 (12)0.0308 (16)
O50.0314 (12)0.0411 (13)0.0703 (14)0.0044 (9)0.0100 (10)0.0081 (11)
O60.0604 (18)0.0370 (14)0.140 (3)−0.0056 (13)0.0168 (18)−0.0061 (15)
O70.0422 (16)0.0554 (17)0.158 (3)−0.0182 (13)0.0219 (17)−0.0232 (18)
O80.0266 (14)0.0729 (19)0.198 (4)−0.0097 (13)0.0017 (17)−0.043 (2)
O90.0250 (12)0.0535 (14)0.0808 (17)0.0039 (10)0.0122 (11)−0.0022 (12)
O100.065 (6)0.083 (7)0.061 (7)0.008 (6)0.017 (5)0.018 (6)
O110.072 (6)0.067 (6)0.080 (8)0.001 (5)0.032 (5)0.004 (6)
Geometric parameters (Å, °) top
C1—N11.318 (5)C24—N31.345 (5)
C1—C21.393 (5)C25—O21.244 (4)
C1—H10.9300C25—O11.249 (4)
C2—C31.341 (6)C25—C261.511 (5)
C2—H20.9300C25—Cu12.539 (4)
C3—C41.401 (6)C26—C271.392 (5)
C3—H30.9300C26—C321.400 (4)
C4—C121.407 (5)C27—C291.391 (5)
C4—C51.448 (6)C27—C281.495 (5)
C5—C61.311 (6)C28—O41.209 (4)
C5—H50.9300C28—O31.311 (4)
C6—C71.433 (6)C29—C301.396 (4)
C6—H60.9300C29—H290.9300
C7—C81.400 (6)C30—C311.383 (5)
C7—C111.401 (5)C30—C331.491 (4)
C8—C91.354 (6)C31—C321.388 (5)
C8—H80.9300C31—H310.9300
C9—C101.393 (6)C32—H320.9300
C9—H90.9300C33—O51.205 (4)
C10—N21.316 (5)C33—C341.504 (4)
C10—H100.9300C34—C351.386 (4)
C11—N21.364 (4)C34—C411.390 (4)
C11—C121.436 (5)C35—C361.396 (4)
C12—N11.363 (5)C35—H350.9300
C13—N31.321 (5)C36—C381.417 (5)
C13—C141.391 (5)C36—C371.514 (5)
C13—H130.9300C37—O61.207 (4)
C14—C151.358 (6)C37—O71.290 (4)
C14—H140.9300C38—C401.393 (4)
C15—C161.386 (5)C38—C391.518 (4)
C15—H150.9300C39—O91.226 (4)
C16—C241.406 (5)C39—O81.264 (4)
C16—C171.427 (6)C40—C411.384 (4)
C17—C181.337 (6)C40—H400.9300
C17—H170.9300C41—H410.9300
C18—C191.432 (5)Cu1—O12.085 (2)
C18—H180.9300Cu1—N42.106 (3)
C19—C231.387 (5)Cu1—N22.125 (3)
C19—C201.410 (5)Cu1—N12.139 (3)
C20—C211.356 (6)Cu1—N32.178 (3)
C20—H200.9300Cu1—O22.371 (3)
C21—C221.383 (6)O3—H3A0.8200
C21—H210.9300O7—H70.8200
C22—N41.325 (4)O10—H1W0.821 (11)
C22—H220.9300O10—H2W0.84 (3)
C23—N41.366 (4)O11—H3W0.87 (3)
C23—C241.438 (5)O11—H4W0.83 (4)
N1—C1—C2122.9 (4)C26—C27—C28123.8 (3)
N1—C1—H1118.6O4—C28—O3123.7 (3)
C2—C1—H1118.5O4—C28—C27123.7 (3)
C3—C2—C1119.7 (4)O3—C28—C27112.7 (3)
C3—C2—H2120.2C27—C29—C30121.8 (3)
C1—C2—H2120.1C27—C29—H29119.1
C2—C3—C4120.3 (4)C30—C29—H29119.1
C2—C3—H3119.8C31—C30—C29118.3 (3)
C4—C3—H3119.9C31—C30—C33123.5 (3)
C3—C4—C12116.5 (4)C29—C30—C33118.2 (3)
C3—C4—C5125.5 (4)C30—C31—C32120.7 (3)
C12—C4—C5118.1 (4)C30—C31—H31119.6
C6—C5—C4121.8 (4)C32—C31—H31119.7
C6—C5—H5119.1C31—C32—C26120.9 (3)
C4—C5—H5119.1C31—C32—H32119.5
C5—C6—C7121.9 (4)C26—C32—H32119.6
C5—C6—H6119.1O5—C33—C30120.1 (3)
C7—C6—H6119.0O5—C33—C34118.8 (3)
C8—C7—C11117.4 (4)C30—C33—C34121.0 (3)
C8—C7—C6123.8 (4)C35—C34—C41118.6 (3)
C11—C7—C6118.7 (4)C35—C34—C33117.8 (3)
C9—C8—C7119.7 (4)C41—C34—C33123.3 (3)
C9—C8—H8120.2C34—C35—C36123.3 (3)
C7—C8—H8120.1C34—C35—H35118.4
C8—C9—C10119.3 (4)C36—C35—H35118.3
C8—C9—H9120.5C35—C36—C38117.5 (3)
C10—C9—H9120.3C35—C36—C37114.0 (3)
N2—C10—C9123.3 (4)C38—C36—C37128.4 (3)
N2—C10—H10118.2O6—C37—O7120.5 (4)
C9—C10—H10118.4O6—C37—C36119.5 (3)
N2—C11—C7122.5 (4)O7—C37—C36120.0 (4)
N2—C11—C12117.7 (3)C40—C38—C36118.6 (3)
C7—C11—C12119.8 (3)C40—C38—C39114.0 (3)
N1—C12—C4122.9 (4)C36—C38—C39127.3 (3)
N1—C12—C11117.3 (3)O9—C39—O8121.6 (3)
C4—C12—C11119.7 (4)O9—C39—C38118.7 (3)
N3—C13—C14122.3 (4)O8—C39—C38119.6 (4)
N3—C13—H13118.8C41—C40—C38122.7 (3)
C14—C13—H13118.9C41—C40—H40118.7
C15—C14—C13119.8 (4)C38—C40—H40118.7
C15—C14—H14120.0C40—C41—C34119.2 (3)
C13—C14—H14120.1C40—C41—H41120.4
C14—C15—C16119.5 (4)C34—C41—H41120.4
C14—C15—H15120.3O1—Cu1—N4140.77 (10)
C16—C15—H15120.2O1—Cu1—N2107.09 (11)
C15—C16—C24117.3 (4)N4—Cu1—N2110.97 (11)
C15—C16—C17123.9 (4)O1—Cu1—N199.44 (11)
C24—C16—C17118.9 (4)N4—Cu1—N197.14 (11)
C18—C17—C16121.2 (4)N2—Cu1—N178.41 (12)
C18—C17—H17119.4O1—Cu1—N388.70 (11)
C16—C17—H17119.4N4—Cu1—N377.60 (12)
C17—C18—C19121.4 (4)N2—Cu1—N397.19 (12)
C17—C18—H18119.3N1—Cu1—N3171.58 (12)
C19—C18—H18119.3O1—Cu1—O258.28 (9)
C23—C19—C20117.2 (4)N4—Cu1—O286.22 (10)
C23—C19—C18119.1 (4)N2—Cu1—O2160.63 (11)
C20—C19—C18123.7 (4)N1—Cu1—O291.00 (11)
C21—C20—C19119.8 (4)N3—Cu1—O295.17 (11)
C21—C20—H20120.1O1—Cu1—C2529.28 (10)
C19—C20—H20120.1N4—Cu1—C25113.30 (12)
C20—C21—C22119.1 (4)N2—Cu1—C25135.70 (12)
C20—C21—H21120.4N1—Cu1—C2597.53 (11)
C22—C21—H21120.5N3—Cu1—C2590.63 (11)
N4—C22—C21123.5 (4)O2—Cu1—C2529.08 (10)
N4—C22—H22118.2C1—N1—C12117.6 (3)
C21—C22—H22118.3C1—N1—Cu1129.3 (3)
N4—C23—C19122.9 (3)C12—N1—Cu1113.1 (2)
N4—C23—C24117.2 (3)C10—N2—C11117.7 (3)
C19—C23—C24119.9 (3)C10—N2—Cu1128.9 (3)
N3—C24—C16122.9 (4)C11—N2—Cu1113.4 (3)
N3—C24—C23117.5 (3)C13—N3—C24118.1 (3)
C16—C24—C23119.5 (4)C13—N3—Cu1128.9 (3)
O2—C25—O1122.5 (3)C24—N3—Cu1112.7 (2)
O2—C25—C26117.8 (3)C22—N4—C23117.5 (3)
O1—C25—C26119.5 (3)C22—N4—Cu1127.7 (3)
O2—C25—Cu167.9 (2)C23—N4—Cu1114.4 (2)
O1—C25—Cu154.76 (18)C25—O1—Cu196.0 (2)
C26—C25—Cu1168.3 (2)C25—O2—Cu183.0 (2)
C27—C26—C32118.8 (3)C28—O3—H3A109.6
C27—C26—C25125.6 (3)C37—O7—H7109.4
C32—C26—C25115.6 (3)H1W—O10—H2W112 (3)
C29—C27—C26119.5 (3)H3W—O11—H4W122 (4)
C29—C27—C28116.7 (3)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O11—H4W···O6i0.83 (4)2.58 (5)2.764 (14)94 (4)
O3—H3A···O8ii0.822.563.198 (4)136
O3—H3A···O9ii0.821.772.555 (3)161
Symmetry codes: (i) x, y+1, z; (ii) x+1, y, z.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O11—H4W···O6i0.83 (4)2.58 (5)2.764 (14)94 (4)
O3—H3A···O8ii0.822.563.198 (4)136
O3—H3A···O9ii0.821.772.555 (3)161
Symmetry codes: (i) x, y+1, z; (ii) x+1, y, z.
references
References top

Bruker (2001). SMART, SAINT-Plus, SADABS and SHELXTL. Bruker AXS Inc., Madison, Wisconsin, USA. [SMART not cited - may it be removed?]

Bruker (2004). APEX2. Bruker AXS Inc., Madison , Wisconsin , USA .

Chung, L., Rajan, K. S., Merdinger, E. & Grecz, N. (1971). Biophys. J. 11, 469–482.

Church, B. S. & Halvorson, H. (1959). Nature (London), 183, 124–125.

Kim, Y., Lee, E. & Jung, D. Y. (2001). Chem. Mater. 13, 2684–2690.

Okabe, N. & Oya, N. (2000). Acta Cryst. C56, 1416–1417.

Pocker, Y. & Fong, C. T. O. (1980). Biochemistry, 19, 2045–2049.

Scapin, G., Reddy, S. G., Zheng, R. & Blanchard, J. S. (1997). Biochemistry, 36, 15081–15088.

Serre, C., Marrot, J. & Férey, G. (2005). Inorg. Chem. 44, 654–658.

Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.