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Acta Crystallogr Sect E Struct Rep Online. 2010 May 1; 66(Pt 5): m568.
Published online 2010 April 24. doi:  10.1107/S1600536810014224
PMCID: PMC2979115

Poly[tetra­kis(2,2′-bipyridine)undeca-μ-oxido-hexa­oxidodicopper(II)hexa­vanadium(V)]

Abstract

In the title organic–inorganic hybrid vanadate complex, [Cu2V6O17(C10H8N2)4]n, the CuII atom is six-coordinated by two chelating 2,2′-bipyridine (bipy) ligands and two vanadate O atoms in a distorted octa­hedral geometry. Two [Cu(bipy)2V3O8] units are linked by a bridging O atom, which lies on an inversion center, forming a dimeric unit. The dimeric units are further connected by bridging vanadate O atoms into a two-dimensional layer parallel to (100). The layers are connected by weak C—H(...)O hydrogen bonds.

Related literature

For the introduction of some transition metal complexes into inorganic framework structures, see: Cao et al. (2003 [triangle]); Liu et al. (2001 [triangle]); Zhang et al. (2000 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0m568-scheme1.jpg

Experimental

Crystal data

  • [Cu2V6O17(C10H8N2)4]
  • M r = 1329.46
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0m568-efi1.jpg
  • a = 15.512 (3) Å
  • b = 14.761 (3) Å
  • c = 10.470 (2) Å
  • β = 92.00 (3)°
  • V = 2395.9 (8) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 2.07 mm−1
  • T = 293 K
  • 0.57 × 0.40 × 0.30 mm

Data collection

  • Rigaku R-AXIS RAPID diffractometer
  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995 [triangle]) T min = 0.385, T max = 0.577
  • 20154 measured reflections
  • 4742 independent reflections
  • 4010 reflections with I > 2σ(I)
  • R int = 0.027

Refinement

  • R[F 2 > 2σ(F 2)] = 0.031
  • wR(F 2) = 0.087
  • S = 1.05
  • 4742 reflections
  • 395 parameters
  • All H-atom parameters refined
  • Δρmax = 0.47 e Å−3
  • Δρmin = −0.67 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998 [triangle]); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810014224/hy2298sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810014224/hy2298Isup2.hkl

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

Acknowledgments

This work was supported financially by the National Natural Science Foundation of Heilongjiang Province (Nos. B200901 and B200917) and the Science and Technology Research Key Project of Jiamusi University (No. Lz2009-015).

supplementary crystallographic information

Comment

An important advance for the design of organic-inorganic hybrid materials is to introduce some transition metal complexes (TMCs) into the backbone of inorganic oxides (Liu et al., 2001; Zhang et al., 2000). We are interested in introducing transition metal complexes into inorganic frameworks and understanding the role of metal complexes on the modification of inorganic framework structures (Cao et al., 2003). In an effort to further explore the structural diversity of the M/V/O/L system (M = transition metal, L = organic ligand), we have prepared the title compound.

The asymmetric unit of the title compound contains a [Cu(bipy)2(V3O8.5)] (bipy = 2,2'-bipyridine) unit, as shown in Fig.1. The VV centers exhibit VO4 tetrahedral coordination environments with V—Ot (terminal O atom) distances ranging from 1.580 (3) to 1.610 (2) Å and V—Ob (bridging O atom) distances ranging from 1.630 (2) to 1.821 (2) Å. The CuII atom is six-coordinated by two bipy ligands and two vanadate O atoms (O1 and O4) in a distorted octahedral geometry, with Cu—N = 2.055 (2)–2.125 (2) Å and Cu—O = 2.025 (2) and 2.082 (2) Å. Two [Cu(bipy)2V3O8] units are linked by a bridging O2 atom, which lies on an inversion center, with a V—O distance of 1.7813 (6) Å, generating a dimeric [Cu2(bipy)4V6O17] unit. As illustrated in Fig. 2, each dimeric unit is joined to four adjacent ones through O6 and its symmetry equivalents, generating a two-dimensional network grafted with [Cu(bipy)2]2+ complex. In addition, the adjacent two-dimension layers further stack into a three-dimensional structure via weak C—H···O hydrogen-bonding interactions (Table 1).

Experimental

A mixture of Na2WO4.2H2O (1.20 g, 3.6 mmol), V2O5 (0.33 g, 1.8 mmol), Cu(CH3CO2)2.4H2O (0.3 g, 1.2 mmol), bipy (0.18 g, 1.2 mmol) and distilled water (20 ml, 1111 mmol) in a molar ratio of 6:3:2:2:1850 was stirred for 120 min. The pH value of the mixture was necessarily adjusted to 4 with dilute H3PO4 solution. The resultant mixture was sealed in a 25 ml Teflon-lined autoclave and heated at 553 K for 72 h. The autoclave was then cooled to room temperature. The crystalline product was filtered, washed with distilled water and dried at ambient temperature to give 0.335 g solids of the title compound.

Refinement

All H atoms were located from difference Fourier maps and refined isotropically.

Figures

Fig. 1.
The asymmetric unit of the title compound, with displacement ellipsoids at the 50% probability level.
Fig. 2.
A polyhedral representation of the two-dimensional layer-like structure in the title compound. H and C atoms of bipy molecules are omitted for clarity.

Crystal data

[Cu2V6O17(C10H8N2)4]F(000) = 1320
Mr = 1329.46Dx = 1.843 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 7302 reflections
a = 15.512 (3) Åθ = 2.4–26.0°
b = 14.761 (3) ŵ = 2.07 mm1
c = 10.470 (2) ÅT = 293 K
β = 92.00 (3)°Block, red
V = 2395.9 (8) Å30.57 × 0.40 × 0.30 mm
Z = 2

Data collection

Rigaku R-AXIS RAPID diffractometer4742 independent reflections
Radiation source: fine-focus sealed tube4010 reflections with I > 2σ(I)
graphiteRint = 0.027
Detector resolution: 10 pixels mm-1θmax = 26.1°, θmin = 2.4°
ω scansh = −19→19
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)k = −18→18
Tmin = 0.385, Tmax = 0.577l = −12→12
20154 measured reflections

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)] = 0.031Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.087All H-atom parameters refined
S = 1.05w = 1/[σ2(Fo2) + (0.0468P)2 + 1.8261P] where P = (Fo2 + 2Fc2)/3
4742 reflections(Δ/σ)max = 0.001
395 parametersΔρmax = 0.47 e Å3
0 restraintsΔρmin = −0.67 e Å3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
Cu10.23318 (2)0.97904 (2)0.20082 (3)0.02820 (11)
V10.08531 (3)1.05781 (3)0.42475 (4)0.02542 (12)
V20.31303 (3)1.19857 (3)0.31446 (4)0.02286 (12)
V30.25041 (3)1.14320 (3)0.60425 (4)0.02692 (12)
O10.14691 (13)0.98560 (13)0.3484 (2)0.0341 (5)
O20.00001.00000.50000.0553 (10)
O30.04662 (16)1.13047 (15)0.3236 (2)0.0510 (6)
O40.27773 (15)1.10202 (14)0.2580 (2)0.0427 (5)
O50.41332 (14)1.21072 (16)0.2836 (2)0.0436 (5)
O60.25003 (15)1.28957 (15)0.2414 (2)0.0430 (5)
O70.30503 (16)1.20006 (18)0.4860 (2)0.0510 (6)
O80.14570 (16)1.12151 (18)0.5470 (2)0.0551 (7)
O90.2978 (2)1.05097 (19)0.6372 (3)0.0846 (11)
N10.17768 (16)0.86159 (15)0.1249 (2)0.0318 (5)
N20.15122 (14)1.03192 (15)0.0616 (2)0.0268 (5)
N30.32645 (15)0.91624 (15)0.3159 (2)0.0294 (5)
N40.33465 (15)0.96215 (17)0.0718 (2)0.0318 (5)
C10.1889 (2)0.7771 (2)0.1683 (3)0.0430 (8)
C20.1533 (3)0.7026 (2)0.1050 (4)0.0546 (11)
C30.1052 (3)0.7157 (2)−0.0051 (4)0.0527 (10)
C40.0924 (2)0.8026 (2)−0.0504 (4)0.0437 (8)
C50.12893 (18)0.87492 (19)0.0171 (3)0.0313 (6)
C60.11711 (17)0.97065 (19)−0.0214 (3)0.0292 (6)
C70.0741 (2)0.9974 (3)−0.1329 (3)0.0428 (8)
C80.0654 (2)1.0887 (3)−0.1598 (3)0.0453 (8)
C90.0985 (2)1.1508 (2)−0.0744 (3)0.0393 (7)
C100.14073 (19)1.1201 (2)0.0355 (3)0.0333 (6)
C110.3215 (2)0.9033 (2)0.4409 (3)0.0407 (7)
C120.3903 (3)0.8710 (3)0.5148 (4)0.0550 (10)
C130.4660 (3)0.8537 (3)0.4584 (4)0.0615 (12)
C140.4726 (2)0.8668 (3)0.3293 (4)0.0498 (9)
C150.40065 (19)0.8971 (2)0.2594 (3)0.0340 (7)
C160.40090 (19)0.9128 (2)0.1201 (3)0.0343 (6)
C170.4643 (2)0.8791 (3)0.0428 (4)0.0478 (9)
C180.4617 (3)0.8992 (3)−0.0851 (4)0.0562 (10)
C190.3964 (2)0.9526 (3)−0.1333 (3)0.0509 (9)
C200.3348 (2)0.9822 (3)−0.0522 (3)0.0409 (8)
H10.299 (2)1.013 (2)−0.078 (3)0.032 (9)*
H20.387 (2)0.969 (3)−0.223 (4)0.057 (11)*
H30.508 (3)0.880 (2)−0.129 (4)0.053 (11)*
H40.498 (2)0.846 (3)0.078 (4)0.050 (11)*
H50.522 (3)0.856 (2)0.292 (3)0.052 (11)*
H60.510 (3)0.835 (3)0.498 (4)0.065 (12)*
H70.384 (3)0.867 (3)0.598 (4)0.072 (13)*
H80.272 (2)0.916 (2)0.474 (3)0.030 (8)*
H90.1628 (19)1.159 (2)0.094 (3)0.026 (8)*
H100.091 (2)1.207 (3)−0.088 (3)0.052 (11)*
H110.034 (3)1.110 (3)−0.245 (4)0.070 (12)*
H120.056 (2)0.956 (3)−0.177 (4)0.050 (11)*
H130.065 (3)0.813 (3)−0.128 (4)0.072 (14)*
H140.077 (3)0.658 (3)−0.049 (4)0.077 (13)*
H150.164 (3)0.651 (3)0.129 (4)0.060 (12)*
H160.223 (2)0.772 (2)0.247 (3)0.040 (9)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cu10.02821 (19)0.02505 (19)0.0313 (2)0.00175 (13)−0.00022 (14)−0.00123 (13)
V10.0201 (2)0.0241 (2)0.0322 (3)−0.00464 (17)0.00256 (18)−0.00629 (18)
V20.0239 (2)0.0238 (2)0.0208 (2)−0.00305 (17)−0.00113 (17)0.00312 (17)
V30.0344 (3)0.0247 (2)0.0215 (2)0.00049 (19)−0.00231 (19)−0.00010 (18)
O10.0324 (11)0.0333 (11)0.0370 (11)0.0057 (9)0.0089 (9)−0.0015 (9)
O20.0417 (19)0.0462 (19)0.080 (3)−0.0205 (16)0.0305 (18)−0.0156 (18)
O30.0606 (16)0.0355 (12)0.0561 (15)0.0119 (11)−0.0094 (12)−0.0029 (11)
O40.0535 (14)0.0283 (11)0.0450 (13)−0.0079 (10)−0.0142 (11)−0.0008 (9)
O50.0289 (11)0.0584 (15)0.0438 (13)−0.0057 (10)0.0052 (9)0.0031 (11)
O60.0523 (14)0.0443 (13)0.0329 (11)0.0190 (11)0.0073 (10)0.0107 (10)
O70.0553 (15)0.0756 (17)0.0221 (11)−0.0188 (13)0.0007 (10)0.0027 (11)
O80.0452 (14)0.0773 (18)0.0430 (14)−0.0242 (13)0.0016 (11)−0.0233 (12)
O90.140 (3)0.0501 (16)0.0618 (18)0.0471 (18)−0.0262 (19)−0.0005 (14)
N10.0354 (14)0.0246 (12)0.0361 (14)−0.0028 (10)0.0089 (11)−0.0038 (10)
N20.0231 (12)0.0260 (12)0.0312 (12)0.0005 (9)−0.0015 (9)−0.0020 (9)
N30.0325 (13)0.0271 (12)0.0286 (12)0.0054 (10)−0.0012 (10)−0.0004 (9)
N40.0277 (13)0.0359 (13)0.0317 (13)0.0023 (10)0.0020 (10)0.0009 (10)
C10.053 (2)0.0291 (16)0.047 (2)−0.0013 (14)0.0123 (17)−0.0002 (14)
C20.074 (3)0.0237 (17)0.068 (3)−0.0073 (17)0.027 (2)−0.0034 (16)
C30.060 (2)0.0374 (19)0.061 (2)−0.0164 (17)0.0191 (19)−0.0196 (17)
C40.0414 (19)0.0415 (19)0.048 (2)−0.0090 (15)0.0062 (16)−0.0190 (15)
C50.0275 (15)0.0319 (15)0.0350 (16)−0.0018 (12)0.0076 (12)−0.0102 (12)
C60.0220 (13)0.0353 (15)0.0303 (15)−0.0013 (11)0.0019 (11)−0.0073 (12)
C70.0378 (18)0.055 (2)0.0354 (18)−0.0037 (16)−0.0039 (14)−0.0108 (16)
C80.0395 (19)0.059 (2)0.0368 (18)0.0058 (16)−0.0055 (14)0.0090 (16)
C90.0369 (18)0.0387 (18)0.0423 (18)0.0035 (14)0.0011 (14)0.0102 (14)
C100.0311 (16)0.0285 (15)0.0399 (17)0.0003 (12)−0.0034 (13)0.0004 (13)
C110.047 (2)0.0427 (18)0.0322 (17)0.0091 (15)−0.0002 (15)−0.0034 (14)
C120.076 (3)0.056 (2)0.0317 (19)0.014 (2)−0.0137 (18)0.0014 (16)
C130.060 (3)0.067 (3)0.055 (2)0.025 (2)−0.026 (2)−0.0006 (19)
C140.039 (2)0.056 (2)0.054 (2)0.0190 (17)−0.0066 (17)−0.0005 (17)
C150.0329 (16)0.0292 (15)0.0397 (17)0.0067 (12)−0.0023 (13)−0.0009 (12)
C160.0293 (15)0.0335 (15)0.0401 (17)0.0057 (12)0.0023 (13)0.0003 (13)
C170.042 (2)0.050 (2)0.052 (2)0.0176 (17)0.0068 (17)−0.0025 (17)
C180.057 (2)0.063 (2)0.050 (2)0.0111 (19)0.0220 (19)−0.0076 (18)
C190.054 (2)0.065 (2)0.0344 (19)0.0032 (18)0.0077 (16)0.0014 (17)
C200.0333 (18)0.053 (2)0.0360 (18)0.0042 (16)−0.0004 (14)0.0054 (15)

Geometric parameters (Å, °)

Cu1—O42.025 (2)C2—H150.82 (4)
Cu1—N22.055 (2)C3—C41.380 (5)
Cu1—N32.069 (2)C3—H141.06 (4)
Cu1—N12.081 (2)C4—C51.390 (4)
Cu1—O12.082 (2)C4—H130.91 (4)
Cu1—N42.125 (2)C5—C61.479 (4)
V1—O31.609 (2)C6—C71.382 (5)
V1—O11.656 (2)C7—C81.382 (5)
V1—O21.7813 (6)C7—H120.82 (4)
V1—O81.821 (2)C8—C91.367 (5)
V2—O51.610 (2)C8—H111.05 (4)
V2—O41.630 (2)C9—C101.380 (4)
V2—O71.805 (2)C9—H100.85 (4)
V2—O61.814 (2)C10—H90.90 (3)
V3—O91.580 (3)C11—C121.381 (5)
V3—O71.740 (2)C11—H80.87 (3)
V3—O81.741 (2)C12—C131.358 (6)
V3—O6i1.746 (2)C12—H70.88 (4)
O2—V1ii1.7813 (6)C13—C141.373 (6)
O6—V3iii1.746 (2)C13—H60.83 (4)
N1—C11.336 (4)C14—C151.388 (4)
N1—C51.351 (4)C14—H50.89 (4)
N2—C101.338 (4)C15—C161.477 (4)
N2—C61.349 (3)C16—C171.387 (4)
N3—C111.328 (4)C17—C181.370 (5)
N3—C151.342 (4)C17—H40.79 (4)
N4—C201.332 (4)C18—C191.366 (5)
N4—C161.344 (4)C18—H30.90 (4)
C1—C21.389 (5)C19—C201.372 (5)
C1—H160.97 (3)C19—H20.98 (4)
C2—C31.365 (6)C20—H10.77 (3)
O4—Cu1—N293.75 (9)C1—C2—H15121 (3)
O4—Cu1—N390.30 (9)C2—C3—C4119.3 (3)
N2—Cu1—N3170.39 (9)C2—C3—H14117 (2)
O4—Cu1—N1172.68 (9)C4—C3—H14123 (2)
N2—Cu1—N178.93 (10)C3—C4—C5119.2 (4)
N3—Cu1—N196.93 (10)C3—C4—H13121 (3)
O4—Cu1—O187.74 (9)C5—C4—H13120 (3)
N2—Cu1—O196.38 (9)N1—C5—C4121.3 (3)
N3—Cu1—O192.48 (9)N1—C5—C6115.3 (2)
N1—Cu1—O193.10 (9)C4—C5—C6123.4 (3)
O4—Cu1—N492.31 (10)N2—C6—C7121.3 (3)
N2—Cu1—N492.71 (9)N2—C6—C5115.0 (2)
N3—Cu1—N478.41 (9)C7—C6—C5123.7 (3)
N1—Cu1—N488.01 (9)C6—C7—C8119.5 (3)
O1—Cu1—N4170.89 (9)C6—C7—H12114 (3)
O3—V1—O1108.66 (12)C8—C7—H12126 (3)
O3—V1—O2110.17 (10)C9—C8—C7119.2 (3)
O1—V1—O2110.81 (8)C9—C8—H11120 (2)
O3—V1—O8106.82 (13)C7—C8—H11121 (2)
O1—V1—O8112.34 (12)C8—C9—C10118.8 (3)
O2—V1—O8107.96 (8)C8—C9—H10120 (3)
O5—V2—O4109.82 (12)C10—C9—H10121 (3)
O5—V2—O7107.40 (12)N2—C10—C9122.7 (3)
O4—V2—O7109.75 (11)N2—C10—H9116.5 (19)
O5—V2—O6110.05 (11)C9—C10—H9120.8 (19)
O4—V2—O6108.97 (11)N3—C11—C12122.1 (3)
O7—V2—O6110.83 (11)N3—C11—H8116 (2)
O9—V3—O7109.65 (17)C12—C11—H8122 (2)
O9—V3—O8109.78 (17)C13—C12—C11119.0 (4)
O7—V3—O8108.38 (12)C13—C12—H7123 (3)
O9—V3—O6i108.97 (14)C11—C12—H7118 (3)
O7—V3—O6i109.07 (11)C12—C13—C14119.9 (3)
O8—V3—O6i110.97 (12)C12—C13—H6124 (3)
V1—O1—Cu1141.73 (12)C14—C13—H6116 (3)
V1ii—O2—V1180.00 (3)C13—C14—C15118.6 (4)
V2—O4—Cu1175.90 (14)C13—C14—H5120 (2)
V3iii—O6—V2138.61 (13)C15—C14—H5121 (2)
V3—O7—V2138.95 (15)N3—C15—C14121.5 (3)
V3—O8—V1141.98 (16)N3—C15—C16115.7 (3)
C1—N1—C5118.9 (3)C14—C15—C16122.8 (3)
C1—N1—Cu1126.9 (2)N4—C16—C17121.5 (3)
C5—N1—Cu1114.19 (18)N4—C16—C15115.3 (3)
C10—N2—C6118.6 (3)C17—C16—C15123.1 (3)
C10—N2—Cu1125.6 (2)C18—C17—C16119.7 (3)
C6—N2—Cu1114.90 (18)C18—C17—H4125 (3)
C11—N3—C15119.0 (3)C16—C17—H4115 (3)
C11—N3—Cu1125.1 (2)C19—C18—C17118.8 (3)
C15—N3—Cu1115.52 (19)C19—C18—H3125 (2)
C20—N4—C16117.4 (3)C17—C18—H3115 (2)
C20—N4—Cu1128.3 (2)C18—C19—C20118.6 (3)
C16—N4—Cu1113.47 (19)C18—C19—H2126 (2)
N1—C1—C2122.1 (4)C20—C19—H2115 (2)
N1—C1—H16116 (2)N4—C20—C19123.9 (3)
C2—C1—H16122 (2)N4—C20—H1117 (3)
C3—C2—C1119.2 (4)C19—C20—H1119 (3)
C3—C2—H15119 (3)
O3—V1—O1—Cu136.1 (2)N1—Cu1—N4—C16−90.4 (2)
O2—V1—O1—Cu1157.26 (16)C5—N1—C1—C21.1 (5)
O8—V1—O1—Cu1−81.9 (2)Cu1—N1—C1—C2−175.5 (3)
O4—Cu1—O1—V137.4 (2)N1—C1—C2—C30.0 (6)
N2—Cu1—O1—V1−56.2 (2)C1—C2—C3—C4−0.6 (6)
N3—Cu1—O1—V1127.6 (2)C2—C3—C4—C50.1 (5)
N1—Cu1—O1—V1−135.4 (2)C1—N1—C5—C4−1.6 (4)
O5—V2—O6—V3iii33.7 (3)Cu1—N1—C5—C4175.4 (2)
O4—V2—O6—V3iii−86.8 (2)C1—N1—C5—C6177.8 (3)
O7—V2—O6—V3iii152.3 (2)Cu1—N1—C5—C6−5.3 (3)
O9—V3—O7—V281.2 (3)C3—C4—C5—N11.0 (5)
O8—V3—O7—V2−38.6 (3)C3—C4—C5—C6−178.3 (3)
O6i—V3—O7—V2−159.5 (2)C10—N2—C6—C71.7 (4)
O5—V2—O7—V3−138.5 (2)Cu1—N2—C6—C7−167.8 (2)
O4—V2—O7—V3−19.1 (3)C10—N2—C6—C5−177.9 (2)
O6—V2—O7—V3101.3 (3)Cu1—N2—C6—C512.6 (3)
O9—V3—O8—V1−54.8 (3)N1—C5—C6—N2−4.8 (4)
O7—V3—O8—V164.9 (3)C4—C5—C6—N2174.6 (3)
O6i—V3—O8—V1−175.4 (2)N1—C5—C6—C7175.7 (3)
O3—V1—O8—V3−109.6 (3)C4—C5—C6—C7−5.0 (5)
O1—V1—O8—V39.4 (3)N2—C6—C7—C8−0.4 (5)
O2—V1—O8—V3131.9 (2)C5—C6—C7—C8179.1 (3)
N2—Cu1—N1—C1−174.2 (3)C6—C7—C8—C9−0.9 (5)
N3—Cu1—N1—C114.6 (3)C7—C8—C9—C100.8 (5)
O1—Cu1—N1—C1−78.3 (3)C6—N2—C10—C9−1.8 (4)
N4—Cu1—N1—C192.6 (3)Cu1—N2—C10—C9166.5 (2)
N2—Cu1—N1—C59.10 (19)C8—C9—C10—N20.6 (5)
N3—Cu1—N1—C5−162.12 (19)C15—N3—C11—C120.1 (5)
O1—Cu1—N1—C5105.0 (2)Cu1—N3—C11—C12−171.9 (3)
N4—Cu1—N1—C5−84.0 (2)N3—C11—C12—C131.4 (6)
O4—Cu1—N2—C10−0.6 (2)C11—C12—C13—C14−1.2 (6)
N1—Cu1—N2—C10179.4 (3)C12—C13—C14—C15−0.4 (6)
O1—Cu1—N2—C1087.5 (2)C11—N3—C15—C14−1.9 (5)
N4—Cu1—N2—C10−93.1 (2)Cu1—N3—C15—C14170.9 (3)
O4—Cu1—N2—C6168.1 (2)C11—N3—C15—C16179.7 (3)
N1—Cu1—N2—C6−11.84 (19)Cu1—N3—C15—C16−7.5 (3)
O1—Cu1—N2—C6−103.8 (2)C13—C14—C15—N32.0 (5)
N4—Cu1—N2—C675.6 (2)C13—C14—C15—C16−179.6 (3)
O4—Cu1—N3—C1180.5 (3)C20—N4—C16—C17−3.9 (5)
N1—Cu1—N3—C11−100.6 (3)Cu1—N4—C16—C17166.7 (3)
O1—Cu1—N3—C11−7.2 (3)C20—N4—C16—C15176.4 (3)
N4—Cu1—N3—C11172.8 (3)Cu1—N4—C16—C15−13.0 (3)
O4—Cu1—N3—C15−91.7 (2)N3—C15—C16—N413.9 (4)
N1—Cu1—N3—C1587.1 (2)C14—C15—C16—N4−164.5 (3)
O1—Cu1—N3—C15−179.5 (2)N3—C15—C16—C17−165.8 (3)
N4—Cu1—N3—C150.6 (2)C14—C15—C16—C1715.8 (5)
O4—Cu1—N4—C20−93.8 (3)N4—C16—C17—C182.6 (5)
N2—Cu1—N4—C200.1 (3)C15—C16—C17—C18−177.8 (3)
N3—Cu1—N4—C20176.4 (3)C16—C17—C18—C190.2 (6)
N1—Cu1—N4—C2078.9 (3)C17—C18—C19—C20−1.5 (6)
O4—Cu1—N4—C1696.9 (2)C16—N4—C20—C192.6 (5)
N2—Cu1—N4—C16−169.2 (2)Cu1—N4—C20—C19−166.4 (3)
N3—Cu1—N4—C167.1 (2)C18—C19—C20—N40.1 (6)

Symmetry codes: (i) x, −y+5/2, z+1/2; (ii) −x, −y+2, −z+1; (iii) x, −y+5/2, z−1/2.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C11—H8···O10.87 (3)2.52 (3)3.093 (4)124 (2)
C14—H5···O5iv0.89 (4)2.51 (3)3.159 (5)131 (3)
C18—H3···O5v0.90 (4)2.46 (4)3.315 (5)157 (3)
C19—H2···O9vi0.98 (4)2.32 (4)3.156 (5)144 (3)

Symmetry codes: (iv) −x+1, y−1/2, −z+1/2; (v) −x+1, −y+2, −z; (vi) x, y, z−1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HY2298).

References

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