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Acta Crystallogr Sect E Struct Rep Online. 2009 December 1; 65(Pt 12): m1532.
Published online 2009 November 7. doi:  10.1107/S1600536809043189
PMCID: PMC2972094

(Benzoato-κO)(benzoic acid-κO)(4,4′-dimethyl-2,2′-bipyridine-κ2 N,N′)hydroxidocopper(II) monohydrate

Abstract

In the structure of the title complex, [Cu(C7H5O2)(OH)(C12H12N2)(C7H6O2)]·H2O, the CuII ion is penta­coordinated in a tetra­gonal-pyramidal geometry with one O atom of a hydroxide group, one O atom of a benzoate anion and two N atoms of a 4,4′-dimethyl-2,2′-bipyridine ligand occupying the basal plane, and one O atom of a benzoic acid mol­ecule located at the apical site. The title complex was refined with a metal-coordinated OH group and a ‘free’ benzoic acid molecule, although it can be assumed that the proton is delocalized between the OH and the COOH group. The uncoordinated water mol­ecule is equally disordered over two positions. The structure displays O—H(...)O hydrogen bonding.

Related literature

For selected 4,4′-dimethyl-2,2′-bipyridine copper complexes, see: Deschamps et al. (2002 [triangle]); Dong et al. (2006 [triangle]); Feng et al. (2007 [triangle]); Lin et al. (2008 [triangle]); Qian & Huang (2006 [triangle]); Willett et al. (2001 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-m1532-scheme1.jpg

Experimental

Crystal data

  • [Cu(C7H5O2)(OH)(C12H12N2)(C7H6O2)]·H2O
  • M r = 526.03
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-m1532-efi1.jpg
  • a = 11.3325 (15) Å
  • b = 17.155 (2) Å
  • c = 13.4007 (18) Å
  • β = 98.049 (3)°
  • V = 2579.5 (6) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.89 mm−1
  • T = 296 K
  • 0.28 × 0.26 × 0.25 mm

Data collection

  • Bruker SMART APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.789, T max = 0.808
  • 13741 measured reflections
  • 4538 independent reflections
  • 3075 reflections with I > 2σ(I)
  • R int = 0.053

Refinement

  • R[F 2 > 2σ(F 2)] = 0.053
  • wR(F 2) = 0.146
  • S = 0.95
  • 4538 reflections
  • 329 parameters
  • H-atom parameters constrained
  • Δρmax = 0.53 e Å−3
  • Δρmin = −0.25 e Å−3

Data collection: APEX2 (Bruker, 2005 [triangle]); cell refinement: SAINT (Bruker, 2005 [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/S1600536809043189/zq2009sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809043189/zq2009Isup2.hkl

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

supplementary crystallographic information

Comment

As a contribution to structural characterization of 4,4'-dimethyl-2,2'-bipyridine copper complexes (Deschamps et al., 2002; Dong et al., 2006; Feng et al., 2007; Lin et al. 2008; Qian & Huang, 2006; Willett et al., 2001), we present here the crystal structure of the title complex, [CuLL'L''(OH)].H2O (L = benzoate, L' = benzoic acid, L'' = 4,4'-dimethyl-2,2'-bipyridine).

In the structure of the title complex, the short O2···O5 separation of 2.636 (5) Å clearly indicates a typical hydrogen bond. The corresponding hydrogen atom was located in the Fourier difference maps near O2 (hydroxido benzoic acid type complex A) although general chemical considerations would rather expect it on O5 (water benzoate type complex B). One can assume that the proton is delocalised somewhere in-between as presented in Scheme 1 but based on the X-ray data only, the title complex was finally refined with a metal-coordinated OH group and a "free" benzoic acid molecule.

In the complex, the Cu2+ ion is pentacoordinated, with two N atoms of 4,4'-dimethyl-2,2'-bipyridine, one O atom of a hydroxide group and one O atom of a benzoate anion in the basal plane and one O atom of a benzoic acid molecule completing the square-pyramidal geometry from the apical site (Fig. 1). The atoms N1, N2, O1 and O3 are nearly coplanar, and the Cu atom is displaced by 0.2309 (5) Å from this plane towards the apical O atom. The water solvent molecule is disordered over two positions in a 1:1 ratio.

With O—H···O hydrogen bonds (Table 1), an one-dimensional chain is formed as shown in Fig. 2.

Experimental

The title compound was synthesized hydrothermally in a Teflon-lined autoclave (25 ml) by heating a mixture of 4,4'-dimethyl-2,2'-bipyridine (0.2 mmol), benzoic acid (0.4 mmol) and CuSO4.5H2O (0.2 mmol) in water (10 ml) at 393 K for 3 d. Suitable crystals for an X-ray analysis were obtained.

Refinement

All H atoms were included in calculated positions, with C—H bond lengths fixed at 0.96 Å (methyl CH3), 0.93 Å (aryl group) and O—H = 0.85 Å and were refined in the riding-model approximation. Uiso(H) values were calculated at 1.5 Ueq(C) for methyl H atoms and 1.2 Ueq(C) for the other H atoms.

Figures

Fig. 1.
The molecular structure of the title compound with the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are presented as small spheres of arbitrary radius.
Fig. 2.
Crystal packing of the title compound. Hydrogen-bond interactions are drawn with dashed lines.

Crystal data

[Cu(C7H5O2)(OH)(C12H12N2)(C7H6O2)]·H2OF(000) = 1092
Mr = 526.03Dx = 1.355 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3905 reflections
a = 11.3325 (15) Åθ = 2.8–24.2°
b = 17.155 (2) ŵ = 0.89 mm1
c = 13.4007 (18) ÅT = 296 K
β = 98.049 (3)°Block, colourless
V = 2579.5 (6) Å30.28 × 0.26 × 0.25 mm
Z = 4

Data collection

Bruker SMART APEXII CCD area-detector diffractometer4538 independent reflections
Radiation source: fine-focus sealed tube3075 reflections with I > 2σ(I)
graphiteRint = 0.053
[var phi] and ω scansθmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2005)h = −13→13
Tmin = 0.789, Tmax = 0.808k = −20→11
13741 measured reflectionsl = −14→15

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)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.146H-atom parameters constrained
S = 0.95w = 1/[σ2(Fo2) + (0.0932P)2] where P = (Fo2 + 2Fc2)/3
4538 reflections(Δ/σ)max < 0.001
329 parametersΔρmax = 0.53 e Å3
0 restraintsΔρmin = −0.25 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*/UeqOcc. (<1)
Cu10.09687 (4)0.20024 (2)0.53039 (3)0.05062 (19)
N10.1716 (2)0.09925 (16)0.5797 (2)0.0480 (7)
N20.0537 (2)0.13606 (16)0.40610 (19)0.0450 (7)
O1−0.0650 (2)0.18703 (15)0.6049 (2)0.0656 (7)
O2−0.1757 (3)0.2835 (2)0.5320 (3)0.0854 (9)
H2−0.11160.29890.51780.128*
O30.1942 (2)0.25605 (15)0.63954 (18)0.0631 (7)
O40.1932 (3)0.37656 (17)0.5773 (2)0.0797 (9)
C1−0.1583 (4)0.2267 (3)0.5918 (3)0.0622 (10)
C2−0.2573 (3)0.2055 (2)0.6527 (3)0.0654 (11)
C3−0.2304 (4)0.1691 (3)0.7438 (3)0.0709 (11)
H3−0.15160.15620.76700.085*
C4−0.3181 (5)0.1511 (3)0.8019 (4)0.0877 (14)
H4−0.29840.12600.86350.105*
C5−0.4335 (5)0.1702 (4)0.7687 (4)0.0992 (17)
H5−0.49220.15880.80850.119*
C6−0.4635 (4)0.2054 (4)0.6789 (4)0.1010 (19)
H6−0.54290.21720.65670.121*
C7−0.3759 (4)0.2245 (3)0.6186 (4)0.0898 (15)
H7−0.39650.24940.55700.108*
C80.2201 (3)0.3285 (2)0.6455 (3)0.0548 (9)
C90.2891 (3)0.3544 (2)0.7448 (3)0.0543 (9)
C100.3280 (3)0.4320 (2)0.7563 (3)0.0696 (11)
H100.31370.46640.70230.083*
C110.3871 (4)0.4575 (3)0.8471 (4)0.0825 (14)
H110.41410.50870.85400.099*
C120.4065 (4)0.4069 (3)0.9284 (4)0.0781 (13)
H120.44510.42440.99010.094*
C130.3686 (4)0.3309 (3)0.9178 (3)0.0744 (12)
H130.38210.29680.97210.089*
C140.3098 (3)0.3052 (2)0.8252 (3)0.0616 (10)
H140.28430.25370.81820.074*
C15−0.0037 (3)0.1604 (2)0.3175 (2)0.0522 (9)
H15−0.02640.21250.31070.063*
C16−0.0304 (3)0.1116 (2)0.2362 (3)0.0562 (9)
H16−0.07060.13090.17600.067*
C170.0021 (3)0.0342 (2)0.2435 (2)0.0545 (9)
C18−0.0228 (4)−0.0190 (3)0.1528 (3)0.0783 (13)
H18A−0.0952−0.00300.11200.117*
H18B−0.0310−0.07170.17510.117*
H18C0.0420−0.01610.11390.117*
C190.0616 (3)0.0085 (2)0.3355 (2)0.0499 (8)
H190.0845−0.04340.34370.060*
C200.0867 (3)0.06038 (19)0.4148 (2)0.0423 (8)
C210.1553 (3)0.03960 (19)0.5139 (2)0.0431 (8)
C220.1997 (3)−0.0338 (2)0.5383 (2)0.0480 (8)
H220.1856−0.07410.49160.058*
C230.2658 (3)−0.0484 (2)0.6329 (3)0.0509 (9)
C240.3132 (4)−0.1282 (2)0.6618 (3)0.0672 (11)
H24A0.3985−0.12620.67680.101*
H24B0.2909−0.16370.60700.101*
H24C0.2805−0.14590.72020.101*
C250.2833 (3)0.0141 (2)0.6973 (3)0.0624 (10)
H250.32810.00760.76050.075*
C260.2360 (3)0.0853 (2)0.6704 (3)0.0589 (10)
H260.24860.12600.71650.071*
O50.0289 (3)0.29651 (13)0.46085 (19)0.0677 (8)
H5A0.05600.33500.49240.102*
O1W0.3806 (6)0.4206 (5)0.4579 (5)0.116 (3)0.50
H1WA0.45070.40490.45310.139*0.50
H1WB0.36310.39850.51070.139*0.50
O2W0.3699 (7)0.5847 (4)0.4468 (5)0.112 (2)0.50
H2WA0.34660.54770.48140.135*0.50
H2WB0.30600.60760.42160.135*0.50

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cu10.0706 (3)0.0357 (3)0.0434 (3)−0.0046 (2)0.0005 (2)−0.00101 (19)
N10.0625 (17)0.0394 (15)0.0420 (15)−0.0075 (14)0.0068 (13)−0.0005 (13)
N20.0549 (16)0.0372 (15)0.0427 (15)−0.0046 (14)0.0066 (13)0.0021 (13)
O10.0714 (18)0.0529 (16)0.0737 (18)0.0049 (14)0.0140 (14)−0.0017 (13)
O20.086 (2)0.089 (2)0.076 (2)0.004 (2)−0.0082 (17)0.0052 (18)
O30.0863 (18)0.0440 (16)0.0535 (15)−0.0054 (14)−0.0096 (13)−0.0086 (12)
O40.113 (2)0.0570 (17)0.0635 (17)−0.0284 (17)−0.0080 (16)0.0101 (15)
C10.076 (3)0.052 (2)0.053 (2)−0.003 (2)−0.011 (2)−0.018 (2)
C20.059 (2)0.065 (3)0.070 (3)0.000 (2)0.002 (2)−0.036 (2)
C30.073 (3)0.063 (3)0.077 (3)−0.003 (2)0.010 (2)−0.013 (2)
C40.098 (4)0.079 (3)0.090 (3)−0.009 (3)0.028 (3)−0.021 (3)
C50.086 (4)0.121 (5)0.095 (4)−0.012 (3)0.028 (3)−0.031 (4)
C60.062 (3)0.143 (6)0.096 (4)0.006 (3)0.005 (3)−0.041 (4)
C70.072 (3)0.118 (4)0.075 (3)0.007 (3)−0.006 (2)−0.028 (3)
C80.062 (2)0.048 (2)0.055 (2)−0.008 (2)0.0096 (18)−0.0103 (19)
C90.052 (2)0.051 (2)0.060 (2)−0.0014 (18)0.0075 (17)−0.0180 (19)
C100.071 (3)0.056 (2)0.080 (3)−0.007 (2)0.005 (2)−0.017 (2)
C110.069 (3)0.068 (3)0.106 (4)−0.011 (2)−0.001 (3)−0.041 (3)
C120.060 (3)0.094 (4)0.077 (3)0.002 (3)−0.003 (2)−0.042 (3)
C130.065 (3)0.092 (4)0.064 (3)0.012 (3)0.000 (2)−0.012 (3)
C140.060 (2)0.059 (3)0.065 (2)0.005 (2)0.0040 (19)−0.012 (2)
C150.065 (2)0.043 (2)0.047 (2)0.0012 (18)0.0028 (17)0.0039 (17)
C160.066 (2)0.056 (2)0.043 (2)0.000 (2)−0.0053 (17)0.0024 (17)
C170.062 (2)0.053 (2)0.047 (2)−0.0061 (19)0.0019 (16)−0.0065 (18)
C180.106 (3)0.070 (3)0.054 (2)0.006 (3)−0.006 (2)−0.017 (2)
C190.058 (2)0.0419 (19)0.049 (2)0.0008 (17)0.0061 (16)0.0009 (16)
C200.0477 (18)0.0387 (18)0.0416 (18)−0.0057 (16)0.0102 (14)−0.0001 (15)
C210.0487 (18)0.0388 (18)0.0427 (18)−0.0083 (16)0.0096 (14)0.0025 (15)
C220.057 (2)0.0390 (19)0.0483 (19)−0.0057 (17)0.0074 (15)0.0050 (16)
C230.055 (2)0.046 (2)0.052 (2)−0.0039 (18)0.0106 (16)0.0110 (17)
C240.076 (3)0.057 (2)0.068 (3)0.011 (2)0.009 (2)0.019 (2)
C250.078 (3)0.060 (3)0.044 (2)−0.009 (2)−0.0075 (18)0.0094 (19)
C260.084 (3)0.048 (2)0.042 (2)−0.009 (2)−0.0007 (18)0.0015 (17)
O50.107 (2)0.0367 (14)0.0542 (15)−0.0051 (15)−0.0079 (14)0.0008 (12)
O1W0.115 (5)0.130 (7)0.119 (6)0.009 (5)0.069 (5)0.051 (5)
O2W0.152 (6)0.083 (5)0.101 (5)−0.008 (5)0.013 (5)0.017 (4)

Geometric parameters (Å, °)

Cu1—O31.955 (2)C12—C131.373 (6)
Cu1—O51.997 (2)C12—H120.9300
Cu1—N21.999 (3)C13—C141.396 (5)
Cu1—N11.999 (3)C13—H130.9300
Cu1—O12.219 (3)C14—H140.9300
N1—C211.346 (4)C15—C161.374 (5)
N1—C261.348 (4)C15—H150.9300
N2—C151.338 (4)C16—C171.378 (5)
N2—C201.352 (4)C16—H160.9300
O1—C11.249 (5)C17—C191.391 (4)
O2—C11.258 (5)C17—C181.514 (5)
O2—H20.8200C18—H18A0.9600
O3—C81.276 (5)C18—H18B0.9600
O4—C81.237 (5)C18—H18C0.9600
C1—C21.521 (6)C19—C201.385 (4)
C2—C31.367 (6)C19—H190.9300
C2—C71.396 (6)C20—C211.484 (4)
C3—C41.381 (6)C21—C221.378 (5)
C3—H30.9300C22—C231.402 (5)
C4—C51.361 (7)C22—H220.9300
C4—H40.9300C23—C251.373 (5)
C5—C61.347 (8)C23—C241.502 (5)
C5—H50.9300C24—H24A0.9600
C6—C71.404 (7)C24—H24B0.9600
C6—H60.9300C24—H24C0.9600
C7—H70.9300C25—C261.363 (5)
C8—C91.514 (5)C25—H250.9300
C9—C141.362 (5)C26—H260.9300
C9—C101.404 (5)O5—H5A0.8200
C10—C111.375 (6)O1W—H1WA0.8500
C10—H100.9300O1W—H1WB0.8500
C11—C121.386 (7)O2W—H2WA0.8500
C11—H110.9300O2W—H2WB0.8500
O3—Cu1—O594.85 (10)C13—C12—H12120.0
O3—Cu1—N2159.99 (11)C11—C12—H12120.0
O5—Cu1—N291.90 (10)C12—C13—C14119.7 (5)
O3—Cu1—N190.50 (10)C12—C13—H13120.2
O5—Cu1—N1171.29 (11)C14—C13—H13120.2
N2—Cu1—N180.85 (11)C9—C14—C13121.0 (4)
O3—Cu1—O197.39 (11)C9—C14—H14119.5
O5—Cu1—O190.31 (12)C13—C14—H14119.5
N2—Cu1—O1101.40 (10)N2—C15—C16122.6 (3)
N1—Cu1—O195.82 (10)N2—C15—H15118.7
C21—N1—C26117.6 (3)C16—C15—H15118.7
C21—N1—Cu1115.4 (2)C15—C16—C17120.3 (3)
C26—N1—Cu1127.0 (2)C15—C16—H16119.8
C15—N2—C20118.1 (3)C17—C16—H16119.8
C15—N2—Cu1126.8 (2)C16—C17—C19117.3 (3)
C20—N2—Cu1115.1 (2)C16—C17—C18120.4 (3)
C1—O1—Cu1128.1 (3)C19—C17—C18122.2 (4)
C1—O2—H2109.5C17—C18—H18A109.5
C8—O3—Cu1128.6 (2)C17—C18—H18B109.5
O1—C1—O2124.4 (4)H18A—C18—H18B109.5
O1—C1—C2117.8 (4)C17—C18—H18C109.5
O2—C1—C2117.7 (4)H18A—C18—H18C109.5
C3—C2—C7118.9 (4)H18B—C18—H18C109.5
C3—C2—C1120.0 (4)C20—C19—C17120.0 (3)
C7—C2—C1121.1 (4)C20—C19—H19120.0
C2—C3—C4121.2 (5)C17—C19—H19120.0
C2—C3—H3119.4N2—C20—C19121.7 (3)
C4—C3—H3119.4N2—C20—C21114.3 (3)
C5—C4—C3119.8 (5)C19—C20—C21123.9 (3)
C5—C4—H4120.1N1—C21—C22121.8 (3)
C3—C4—H4120.1N1—C21—C20114.2 (3)
C6—C5—C4120.7 (5)C22—C21—C20124.0 (3)
C6—C5—H5119.6C21—C22—C23120.5 (3)
C4—C5—H5119.6C21—C22—H22119.7
C5—C6—C7120.6 (5)C23—C22—H22119.7
C5—C6—H6119.7C25—C23—C22116.2 (3)
C7—C6—H6119.7C25—C23—C24122.3 (3)
C2—C7—C6118.9 (5)C22—C23—C24121.5 (3)
C2—C7—H7120.6C23—C24—H24A109.5
C6—C7—H7120.6C23—C24—H24B109.5
O4—C8—O3125.0 (3)H24A—C24—H24B109.5
O4—C8—C9119.7 (3)C23—C24—H24C109.5
O3—C8—C9115.3 (3)H24A—C24—H24C109.5
C14—C9—C10119.0 (4)H24B—C24—H24C109.5
C14—C9—C8121.5 (3)C26—C25—C23121.1 (3)
C10—C9—C8119.4 (4)C26—C25—H25119.5
C11—C10—C9120.3 (4)C23—C25—H25119.5
C11—C10—H10119.9N1—C26—C25122.7 (4)
C9—C10—H10119.9N1—C26—H26118.6
C10—C11—C12120.0 (4)C25—C26—H26118.6
C10—C11—H11120.0Cu1—O5—H5A109.5
C12—C11—H11120.0H1WA—O1W—H1WB104.5
C13—C12—C11120.0 (4)H2WA—O2W—H2WB104.5
O3—Cu1—N1—C21−164.4 (2)O4—C8—C9—C10−3.7 (6)
N2—Cu1—N1—C21−2.5 (2)O3—C8—C9—C10176.1 (3)
O1—Cu1—N1—C2198.2 (2)C14—C9—C10—C110.7 (6)
O3—Cu1—N1—C2615.3 (3)C8—C9—C10—C11177.6 (4)
N2—Cu1—N1—C26177.2 (3)C9—C10—C11—C12−1.3 (6)
O1—Cu1—N1—C26−82.2 (3)C10—C11—C12—C131.2 (7)
O3—Cu1—N2—C15−111.7 (4)C11—C12—C13—C14−0.5 (6)
O5—Cu1—N2—C15−1.9 (3)C10—C9—C14—C130.0 (6)
N1—Cu1—N2—C15−177.1 (3)C8—C9—C14—C13−176.9 (3)
O1—Cu1—N2—C1588.8 (3)C12—C13—C14—C90.0 (6)
O3—Cu1—N2—C2068.5 (4)C20—N2—C15—C160.3 (5)
O5—Cu1—N2—C20178.3 (2)Cu1—N2—C15—C16−179.4 (3)
N1—Cu1—N2—C203.2 (2)N2—C15—C16—C17−0.2 (6)
O1—Cu1—N2—C20−91.0 (2)C15—C16—C17—C190.3 (5)
O3—Cu1—O1—C1100.1 (3)C15—C16—C17—C18−177.5 (4)
O5—Cu1—O1—C15.2 (3)C16—C17—C19—C20−0.5 (5)
N2—Cu1—O1—C1−86.8 (3)C18—C17—C19—C20177.2 (4)
N1—Cu1—O1—C1−168.6 (3)C15—N2—C20—C19−0.6 (5)
O5—Cu1—O3—C8−13.1 (3)Cu1—N2—C20—C19179.2 (2)
N2—Cu1—O3—C896.2 (4)C15—N2—C20—C21176.9 (3)
N1—Cu1—O3—C8160.0 (3)Cu1—N2—C20—C21−3.3 (3)
O1—Cu1—O3—C8−104.0 (3)C17—C19—C20—N20.7 (5)
Cu1—O1—C1—O2−0.6 (5)C17—C19—C20—C21−176.6 (3)
Cu1—O1—C1—C2179.9 (2)C26—N1—C21—C221.6 (5)
O1—C1—C2—C326.3 (5)Cu1—N1—C21—C22−178.6 (2)
O2—C1—C2—C3−153.2 (4)C26—N1—C21—C20−178.2 (3)
O1—C1—C2—C7−155.6 (4)Cu1—N1—C21—C201.5 (3)
O2—C1—C2—C724.9 (5)N2—C20—C21—N11.2 (4)
C7—C2—C3—C40.0 (6)C19—C20—C21—N1178.7 (3)
C1—C2—C3—C4178.2 (4)N2—C20—C21—C22−178.7 (3)
C2—C3—C4—C5−0.4 (7)C19—C20—C21—C22−1.2 (5)
C3—C4—C5—C61.1 (8)N1—C21—C22—C23−1.2 (5)
C4—C5—C6—C7−1.3 (9)C20—C21—C22—C23178.6 (3)
C3—C2—C7—C6−0.2 (7)C21—C22—C23—C25−0.3 (5)
C1—C2—C7—C6−178.3 (4)C21—C22—C23—C24178.9 (3)
C5—C6—C7—C20.8 (8)C22—C23—C25—C261.4 (5)
Cu1—O3—C8—O4−5.3 (6)C24—C23—C25—C26−177.8 (3)
Cu1—O3—C8—C9174.9 (2)C21—N1—C26—C25−0.5 (5)
O4—C8—C9—C14173.1 (4)Cu1—N1—C26—C25179.8 (3)
O3—C8—C9—C14−7.0 (5)C23—C25—C26—N1−1.0 (6)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O2W—H2WB···O2i0.852.513.195 (8)138
O2W—H2WA···O1W0.852.242.821 (10)125
O1W—H1WB···O40.852.262.932 (6)136
O1W—H1WA···O2Wii0.852.282.937 (10)134
O5—H5A···O40.821.932.642 (4)145
O2—H2···O50.821.862.636 (5)158

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZQ2009).

References

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