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Acta Crystallogr Sect E Struct Rep Online. 2009 August 1; 65(Pt 8): m933.
Published online 2009 July 18. doi:  10.1107/S1600536809027123
PMCID: PMC2977150

Chlorido[2,2′-(oxydimethyl­ene)­dipyridine]copper(II) perchlorate–aqua­chlorido[2,2′-(oxydimethyl­ene)­dipyridine]copper(II) perchlorate (1/1)

Abstract

The asymmetric unit of the title compound, [CuCl(C12H12N2O)][CuCl(C12H12N2O)(H2O)](ClO4)2, contains two different discrete cations. In one cation, the CuII ion is coordinated in a slightly distorted square-planar geometry, while in the other the CuII ion is in a slightly distorted square-pyramidal environment. In the crystal structure, there are O—H(...)O hydrogen bonds between coordinated water mol­ecules and perchlorate anions. Both types of cations are linked into one-dimensional chains along the b axis by weak electrostatic Cu(...)Cl inter­actions, with Cu(...)Cl distances of 2.8088 (16) and 3.2074 (17) Å.

Related literature

For related structures, see: Li (2007 [triangle], 2008a [triangle],b [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0m933-scheme1.jpg

Experimental

Crystal data

  • [CuCl(C12H12N2O)][CuCl(C12H12N2O)(H2O)](ClO4)2
  • M r = 815.37
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0m933-efi1.jpg
  • a = 10.997 (2) Å
  • b = 12.882 (3) Å
  • c = 12.913 (3) Å
  • α = 97.174 (3)°
  • β = 112.031 (3)°
  • γ = 106.851 (3)°
  • V = 1565.7 (5) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 1.76 mm−1
  • T = 298 K
  • 0.42 × 0.23 × 0.21 mm

Data collection

  • Bruker SMART APEX CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.525, T max = 0.709
  • 8530 measured reflections
  • 6009 independent reflections
  • 4063 reflections with I > 2σ(I)
  • R int = 0.024

Refinement

  • R[F 2 > 2σ(F 2)] = 0.062
  • wR(F 2) = 0.185
  • S = 1.05
  • 6009 reflections
  • 411 parameters
  • 3 restraints
  • H-atom parameters constrained
  • Δρmax = 1.01 e Å−3
  • Δρmin = −0.60 e Å−3

Data collection: SMART (Bruker, 1997 [triangle]); cell refinement: SAINT (Bruker, 1997 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL and PLATON (Spek, 2009 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Selected geometric parameters (Å, °)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809027123/lh2860sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809027123/lh2860Isup2.hkl

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

Acknowledgments

The authors thank the Project of Scientific Studies Development of Shandong Provincial Education Department (grant No. J08LC51) and the Natural Science Foundation of Shandong Province (grant No. Y2007B26).

supplementary crystallographic information

Comment

Derivatives of pyridine play an important role in modern coordination chemistry and some complexes using 2,2'-(oxydimethylene)dipyridine as a ligand have already been reported (Li, 2007, 2008a,b). Herein we report the crystal structure of the title compound.

The molecular structure of the title compound is shown in Fig. 1. Atom Cu1 is in a slightly distorted square-planar coordination environment and atom Cu2 is coordinated in a slightly distorted square-pyramidal environment with the O atom of the coordinated H2O ligand in the apical site. 2,2'-(oxydimethylene)dipyridine acts as a tridentate ligand as in the related CuII, ZnII and CdII complexes (Li, 2007, 2008a,b). In the crystal structure, there are O—H···O hydrogen bonds between coordinated water molecule and perchlorate ions and both types of cation are linked into one-dimensional chains along the b axis by weak electrostatic Cu···Cl interactions with Cu···Cl distances of 2.8088 (16) and 3.2074 (17) Å (see Fig. 2).

Experimental

An 8ml methanol solution of 2,2'-(oxydimetheylene)dipyridine (0.0386 g, 0.193 mmol) was added to an 8 ml H2O solution containing Cu(ClO4)2.6H2O (0.0730 g, 0.197 mmol), and the mixture was stirred for a few minutes. Then, diluted HCl solution was added into the mixed solution in drops until the pH = 4.0. Blue single crystals were obtained after the solution had been allowed to stand at room temperature for three weeks.

Refinement

H2O-bound H atoms were located in a difference Fourier map, and placed in idealized positions with O—H = 0.90 Å and with Uiso(H) = 1.5Ueq(O); other H atoms were placed in calculated positions with C—H = 0.97 Å for methylene group and C—H = 0.93 Å for pyridyl group with Uiso(H) = 1.2Ueq(C). All H atoms were refined in a riding-model approximation.

Figures

Fig. 1.
The asymmetric unit of the title complex with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
Fig. 2.
Part of the crystal structure with hydrogen bonds shown as dashed lines.

Crystal data

[CuCl(C12H12N2O)][CuCl(C12H12N2O)(H2O)](ClO4)2Z = 2
Mr = 815.37F(000) = 824
Triclinic, P1Dx = 1.730 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.997 (2) ÅCell parameters from 2082 reflections
b = 12.882 (3) Åθ = 2.2–23.8°
c = 12.913 (3) ŵ = 1.76 mm1
α = 97.174 (3)°T = 298 K
β = 112.031 (3)°Block, blue
γ = 106.851 (3)°0.42 × 0.23 × 0.21 mm
V = 1565.7 (5) Å3

Data collection

Bruker SMART APEX CCD diffractometer6009 independent reflections
Radiation source: fine-focus sealed tube4063 reflections with I > 2σ(I)
graphiteRint = 0.024
[var phi] and ω scansθmax = 26.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −13→10
Tmin = 0.525, Tmax = 0.709k = −15→15
8530 measured reflectionsl = −15→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)] = 0.062Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.185H-atom parameters constrained
S = 1.05w = 1/[σ2(Fo2) + (0.1088P)2] where P = (Fo2 + 2Fc2)/3
6009 reflections(Δ/σ)max < 0.001
411 parametersΔρmax = 1.01 e Å3
3 restraintsΔρmin = −0.60 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
C10.6320 (7)0.2031 (5)1.2505 (5)0.0595 (16)
H10.70800.22181.23170.071*
C20.6551 (8)0.2240 (6)1.3637 (6)0.078 (2)
H20.74640.25731.42240.093*
C30.5399 (10)0.1947 (7)1.3902 (6)0.085 (2)
H30.55430.20691.46710.102*
C40.4070 (9)0.1483 (6)1.3042 (6)0.073 (2)
H40.32960.13031.32110.088*
C50.3891 (7)0.1283 (5)1.1908 (5)0.0507 (14)
C60.2451 (6)0.0723 (5)1.0915 (5)0.0567 (15)
H6A0.2091−0.00751.08550.068*
H6B0.18030.10471.10310.068*
C70.1462 (6)0.0206 (5)0.8805 (5)0.0583 (15)
H7A0.06850.04710.86070.070*
H7B0.1126−0.05630.88520.070*
C80.2003 (6)0.0257 (5)0.7912 (5)0.0499 (13)
C90.1103 (7)−0.0147 (6)0.6740 (6)0.0661 (17)
H90.0131−0.04380.64920.079*
C100.1668 (8)−0.0112 (7)0.5942 (6)0.074 (2)
H100.1084−0.03950.51530.089*
C110.3108 (8)0.0351 (6)0.6341 (5)0.0664 (17)
H110.35090.03950.58210.080*
C120.3942 (6)0.0742 (5)0.7500 (5)0.0514 (14)
H120.49140.10500.77630.062*
C130.1523 (7)0.3151 (6)0.6299 (5)0.0659 (17)
H130.15440.26230.57510.079*
C140.2190 (6)0.3236 (5)0.7442 (5)0.0572 (15)
H140.26720.27570.76680.069*
C150.0808 (7)0.3866 (6)0.5959 (5)0.073 (2)
H150.03550.38360.51800.088*
C160.0780 (7)0.4616 (6)0.6790 (5)0.0682 (18)
H160.02880.50910.65760.082*
C170.1485 (6)0.4672 (5)0.7953 (5)0.0500 (13)
C180.1488 (7)0.5490 (5)0.8875 (5)0.0558 (14)
H18A0.20630.62470.89400.067*
H18B0.05360.54600.86890.067*
C190.2582 (7)0.6040 (5)1.0978 (5)0.0579 (15)
H19A0.18150.60961.11520.069*
H19B0.30720.67621.08980.069*
C200.3576 (6)0.5727 (5)1.1929 (5)0.0489 (13)
C210.4126 (7)0.6304 (6)1.3080 (5)0.0646 (17)
H210.38540.68901.32790.077*
C220.5060 (7)0.6021 (6)1.3923 (6)0.0704 (18)
H220.54670.64311.46930.084*
C230.5389 (7)0.5114 (6)1.3611 (5)0.0645 (17)
H230.59950.48821.41720.077*
C240.4815 (6)0.4558 (5)1.2464 (5)0.0555 (15)
H240.50370.39441.22570.067*
Cl10.19499 (15)0.84371 (14)0.29265 (13)0.0570 (4)
Cl20.89001 (17)0.69411 (16)0.70403 (14)0.0648 (4)
Cl30.47655 (15)0.34451 (11)0.99732 (12)0.0504 (4)
Cl40.65816 (14)0.13410 (12)1.00771 (12)0.0496 (3)
Cu10.44927 (6)0.12094 (6)0.99775 (5)0.0443 (2)
Cu20.31420 (7)0.41888 (6)0.99518 (5)0.0482 (2)
N10.3943 (5)0.4871 (4)1.1630 (4)0.0453 (10)
N20.2185 (5)0.3987 (4)0.8269 (4)0.0483 (11)
N30.3399 (5)0.0696 (4)0.8284 (4)0.0455 (10)
N40.4983 (5)0.1550 (4)1.1649 (4)0.0492 (11)
O10.2589 (4)0.0900 (3)0.9887 (3)0.0487 (9)
O20.2049 (4)0.5195 (3)0.9940 (3)0.0533 (10)
O31.0211 (5)0.7169 (5)0.6997 (5)0.0934 (16)
O40.8206 (10)0.7530 (10)0.6406 (10)0.221 (5)
O50.9105 (10)0.7257 (15)0.8086 (7)0.335 (10)
O60.8156 (9)0.5888 (7)0.6593 (12)0.253 (7)
O70.1715 (12)0.7738 (12)0.3473 (14)0.304 (9)
O80.3380 (7)0.8819 (6)0.3202 (8)0.157 (3)
O90.1338 (12)0.7967 (16)0.1870 (8)0.356 (12)
O100.1404 (10)0.9200 (9)0.3042 (11)0.218 (5)
O110.1331 (5)0.2760 (4)0.9973 (4)0.0675 (11)
H11A0.12920.31691.05660.101*
H11B0.05160.26760.93810.101*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.065 (4)0.061 (4)0.047 (3)0.026 (3)0.018 (3)0.009 (3)
C20.082 (5)0.078 (5)0.053 (4)0.030 (4)0.012 (4)0.004 (3)
C30.125 (7)0.099 (6)0.048 (4)0.060 (6)0.042 (5)0.017 (4)
C40.102 (6)0.080 (5)0.072 (5)0.050 (5)0.057 (5)0.031 (4)
C50.071 (4)0.045 (3)0.057 (3)0.033 (3)0.039 (3)0.019 (3)
C60.065 (4)0.056 (4)0.072 (4)0.030 (3)0.046 (3)0.023 (3)
C70.042 (3)0.061 (4)0.070 (4)0.021 (3)0.019 (3)0.018 (3)
C80.047 (3)0.048 (3)0.056 (3)0.024 (3)0.018 (3)0.018 (3)
C90.045 (3)0.071 (4)0.064 (4)0.023 (3)0.005 (3)0.016 (3)
C100.077 (5)0.088 (5)0.049 (4)0.039 (4)0.012 (3)0.017 (4)
C110.083 (5)0.072 (5)0.052 (4)0.033 (4)0.032 (3)0.018 (3)
C120.054 (3)0.060 (4)0.046 (3)0.024 (3)0.024 (3)0.020 (3)
C130.079 (5)0.060 (4)0.053 (4)0.015 (4)0.033 (3)0.008 (3)
C140.066 (4)0.052 (4)0.047 (3)0.016 (3)0.024 (3)0.008 (3)
C150.078 (5)0.085 (5)0.041 (4)0.016 (4)0.021 (3)0.014 (3)
C160.073 (4)0.078 (5)0.048 (4)0.030 (4)0.017 (3)0.025 (3)
C170.047 (3)0.052 (4)0.047 (3)0.013 (3)0.020 (3)0.017 (3)
C180.061 (4)0.054 (4)0.054 (3)0.027 (3)0.022 (3)0.018 (3)
C190.080 (4)0.053 (4)0.056 (4)0.037 (3)0.037 (3)0.015 (3)
C200.055 (3)0.046 (3)0.050 (3)0.017 (3)0.029 (3)0.009 (3)
C210.086 (5)0.062 (4)0.049 (4)0.032 (4)0.031 (3)0.009 (3)
C220.081 (5)0.076 (5)0.049 (4)0.022 (4)0.032 (3)0.002 (3)
C230.063 (4)0.072 (5)0.046 (3)0.021 (3)0.013 (3)0.016 (3)
C240.070 (4)0.048 (3)0.051 (3)0.023 (3)0.027 (3)0.016 (3)
Cl10.0530 (9)0.0720 (11)0.0519 (9)0.0266 (8)0.0252 (7)0.0185 (8)
Cl20.0521 (9)0.0780 (12)0.0550 (9)0.0191 (8)0.0207 (7)0.0063 (8)
Cl30.0574 (8)0.0420 (8)0.0598 (8)0.0232 (6)0.0293 (7)0.0150 (6)
Cl40.0424 (7)0.0506 (8)0.0599 (8)0.0209 (6)0.0233 (6)0.0149 (6)
Cu10.0410 (4)0.0507 (4)0.0428 (4)0.0176 (3)0.0196 (3)0.0103 (3)
Cu20.0602 (5)0.0470 (4)0.0409 (4)0.0263 (3)0.0209 (3)0.0102 (3)
N10.054 (3)0.041 (3)0.041 (2)0.016 (2)0.021 (2)0.010 (2)
N20.057 (3)0.041 (3)0.043 (3)0.014 (2)0.021 (2)0.010 (2)
N30.046 (3)0.045 (3)0.043 (3)0.017 (2)0.017 (2)0.010 (2)
N40.063 (3)0.048 (3)0.047 (3)0.027 (2)0.030 (2)0.016 (2)
O10.049 (2)0.051 (2)0.057 (2)0.0208 (18)0.0314 (19)0.0182 (19)
O20.066 (3)0.054 (2)0.045 (2)0.033 (2)0.0210 (18)0.0109 (18)
O30.061 (3)0.107 (4)0.113 (4)0.026 (3)0.042 (3)0.029 (3)
O40.147 (8)0.260 (12)0.351 (15)0.151 (9)0.128 (9)0.141 (11)
O50.136 (8)0.70 (3)0.089 (6)0.059 (12)0.076 (6)−0.015 (10)
O60.111 (6)0.093 (6)0.52 (2)−0.001 (5)0.152 (10)0.014 (9)
O70.200 (10)0.398 (19)0.52 (2)0.167 (12)0.248 (14)0.384 (19)
O80.078 (4)0.124 (6)0.285 (10)0.039 (4)0.084 (5)0.091 (6)
O90.201 (11)0.66 (3)0.104 (7)0.225 (16)−0.020 (7)−0.122 (12)
O100.153 (7)0.171 (9)0.366 (14)0.118 (7)0.112 (8)0.048 (9)
O110.071 (3)0.066 (3)0.066 (3)0.019 (2)0.035 (2)0.019 (2)

Geometric parameters (Å, °)

C1—N41.360 (7)C17—C181.486 (8)
C1—C21.364 (8)C18—O21.430 (6)
C1—H10.9300C18—H18A0.9700
C2—C31.394 (11)C18—H18B0.9700
C2—H20.9300C19—O21.415 (6)
C3—C41.356 (10)C19—C201.496 (8)
C3—H30.9300C19—H19A0.9700
C4—C51.381 (8)C19—H19B0.9700
C4—H40.9300C20—N11.340 (7)
C5—N41.328 (7)C20—C211.385 (8)
C5—C61.502 (9)C21—C221.360 (9)
C6—O11.430 (6)C21—H210.9300
C6—H6A0.9700C22—C231.377 (9)
C6—H6B0.9700C22—H220.9300
C7—O11.426 (7)C23—C241.370 (8)
C7—C81.483 (8)C23—H230.9300
C7—H7A0.9700C24—N11.342 (7)
C7—H7B0.9700C24—H240.9300
C8—N31.335 (7)Cl1—O71.239 (8)
C8—C91.386 (8)Cl1—O91.244 (8)
C9—C101.388 (10)Cl1—O101.313 (7)
C9—H90.9300Cl1—O81.389 (6)
C10—C111.376 (9)Cl2—O51.273 (7)
C10—H100.9300Cl2—O61.285 (8)
C11—C121.360 (8)Cl2—O41.360 (8)
C11—H110.9300Cl2—O31.409 (5)
C12—N31.353 (7)Cl3—Cu22.2511 (15)
C12—H120.9300Cl4—Cu12.2067 (14)
C13—C141.353 (8)Cu1—N31.968 (4)
C13—C151.386 (9)Cu1—O11.970 (3)
C13—H130.9300Cu1—N41.973 (4)
C14—N21.352 (7)Cu2—N21.970 (4)
C14—H140.9300Cu2—N11.972 (4)
C15—C161.367 (9)Cu2—O22.005 (4)
C15—H150.9300Cu2—O112.298 (4)
C16—C171.389 (8)O11—H11A0.8969
C16—H160.9300O11—H11B0.8995
C17—N21.336 (7)
N4—C1—C2120.2 (6)C20—C19—H19B110.1
N4—C1—H1119.9H19A—C19—H19B108.4
C2—C1—H1119.9N1—C20—C21120.4 (5)
C1—C2—C3119.1 (7)N1—C20—C19117.7 (5)
C1—C2—H2120.5C21—C20—C19121.9 (5)
C3—C2—H2120.5C22—C21—C20120.6 (6)
C4—C3—C2120.2 (6)C22—C21—H21119.7
C4—C3—H3119.9C20—C21—H21119.7
C2—C3—H3119.9C21—C22—C23118.5 (6)
C3—C4—C5118.6 (7)C21—C22—H22120.8
C3—C4—H4120.7C23—C22—H22120.8
C5—C4—H4120.7C24—C23—C22119.2 (6)
N4—C5—C4121.6 (6)C24—C23—H23120.4
N4—C5—C6117.1 (5)C22—C23—H23120.4
C4—C5—C6121.3 (6)N1—C24—C23122.1 (6)
O1—C6—C5107.2 (5)N1—C24—H24119.0
O1—C6—H6A110.3C23—C24—H24119.0
C5—C6—H6A110.3O7—Cl1—O9109.6 (11)
O1—C6—H6B110.3O7—Cl1—O10111.8 (7)
C5—C6—H6B110.3O9—Cl1—O10104.2 (8)
H6A—C6—H6B108.5O7—Cl1—O8108.2 (6)
O1—C7—C8108.0 (5)O9—Cl1—O8105.6 (7)
O1—C7—H7A110.1O10—Cl1—O8117.1 (6)
C8—C7—H7A110.1O5—Cl2—O6111.9 (9)
O1—C7—H7B110.1O5—Cl2—O4108.8 (9)
C8—C7—H7B110.1O6—Cl2—O4108.4 (7)
H7A—C7—H7B108.4O5—Cl2—O3109.3 (5)
N3—C8—C9121.3 (5)O6—Cl2—O3109.4 (5)
N3—C8—C7117.1 (5)O4—Cl2—O3108.9 (5)
C9—C8—C7121.6 (6)N3—Cu1—O180.97 (17)
C8—C9—C10119.2 (6)N3—Cu1—N4161.79 (19)
C8—C9—H9120.4O1—Cu1—N481.04 (17)
C10—C9—H9120.4N3—Cu1—Cl498.72 (13)
C11—C10—C9118.8 (6)O1—Cu1—Cl4173.09 (12)
C11—C10—H10120.6N4—Cu1—Cl498.80 (14)
C9—C10—H10120.6N2—Cu2—N1159.85 (19)
C12—C11—C10119.5 (6)N2—Cu2—O280.78 (17)
C12—C11—H11120.2N1—Cu2—O280.45 (16)
C10—C11—H11120.2N2—Cu2—Cl398.32 (14)
N3—C12—C11122.0 (6)N1—Cu2—Cl398.09 (13)
N3—C12—H12119.0O2—Cu2—Cl3165.86 (13)
C11—C12—H12119.0N2—Cu2—O1193.89 (17)
C14—C13—C15118.8 (6)N1—Cu2—O1192.93 (17)
C14—C13—H13120.6O2—Cu2—O1188.68 (16)
C15—C13—H13120.6Cl3—Cu2—O11105.46 (12)
N2—C14—C13122.7 (6)C20—N1—C24119.1 (5)
N2—C14—H14118.6C20—N1—Cu2115.3 (4)
C13—C14—H14118.6C24—N1—Cu2125.5 (4)
C16—C15—C13118.8 (6)C17—N2—C14119.1 (5)
C16—C15—H15120.6C17—N2—Cu2115.1 (4)
C13—C15—H15120.6C14—N2—Cu2125.8 (4)
C15—C16—C17120.2 (6)C8—N3—C12119.2 (5)
C15—C16—H16119.9C8—N3—Cu1115.0 (4)
C17—C16—H16119.9C12—N3—Cu1125.8 (4)
N2—C17—C16120.4 (6)C5—N4—C1120.3 (5)
N2—C17—C18118.3 (5)C5—N4—Cu1115.0 (4)
C16—C17—C18121.3 (6)C1—N4—Cu1124.6 (4)
O2—C18—C17107.8 (5)C7—O1—C6117.4 (5)
O2—C18—H18A110.2C7—O1—Cu1115.1 (3)
C17—C18—H18A110.2C6—O1—Cu1115.1 (3)
O2—C18—H18B110.2C19—O2—C18117.2 (4)
C17—C18—H18B110.2C19—O2—Cu2115.9 (3)
H18A—C18—H18B108.5C18—O2—Cu2115.2 (3)
O2—C19—C20107.9 (4)Cu2—O11—H11A94.6
O2—C19—H19A110.1Cu2—O11—H11B109.4
C20—C19—H19A110.1H11A—O11—H11B101.6
O2—C19—H19B110.1
N4—C1—C2—C30.5 (10)O11—Cu2—N2—C1796.4 (4)
C1—C2—C3—C4−1.4 (11)N1—Cu2—N2—C14166.6 (5)
C2—C3—C4—C51.7 (11)O2—Cu2—N2—C14−171.9 (5)
C3—C4—C5—N4−1.1 (10)Cl3—Cu2—N2—C1422.4 (5)
C3—C4—C5—C6177.2 (6)O11—Cu2—N2—C14−83.8 (5)
N4—C5—C6—O1−16.3 (7)C9—C8—N3—C12−0.3 (8)
C4—C5—C6—O1165.4 (5)C7—C8—N3—C12178.8 (5)
O1—C7—C8—N313.7 (7)C9—C8—N3—Cu1−179.5 (4)
O1—C7—C8—C9−167.1 (5)C7—C8—N3—Cu1−0.3 (6)
N3—C8—C9—C101.2 (9)C11—C12—N3—C8−0.2 (8)
C7—C8—C9—C10−177.9 (6)C11—C12—N3—Cu1178.9 (4)
C8—C9—C10—C11−1.6 (10)O1—Cu1—N3—C8−9.1 (4)
C9—C10—C11—C121.2 (10)N4—Cu1—N3—C8−0.1 (8)
C10—C11—C12—N3−0.3 (10)Cl4—Cu1—N3—C8163.9 (4)
C15—C13—C14—N20.2 (10)O1—Cu1—N3—C12171.7 (5)
C14—C13—C15—C16−1.2 (10)N4—Cu1—N3—C12−179.2 (5)
C13—C15—C16—C171.4 (10)Cl4—Cu1—N3—C12−15.2 (5)
C15—C16—C17—N2−0.6 (9)C4—C5—N4—C10.1 (8)
C15—C16—C17—C18179.2 (6)C6—C5—N4—C1−178.2 (5)
N2—C17—C18—O2−11.5 (7)C4—C5—N4—Cu1−179.3 (5)
C16—C17—C18—O2168.8 (5)C6—C5—N4—Cu12.3 (6)
O2—C19—C20—N110.1 (7)C2—C1—N4—C50.1 (9)
O2—C19—C20—C21−171.0 (5)C2—C1—N4—Cu1179.6 (5)
N1—C20—C21—C220.8 (9)N3—Cu1—N4—C5−0.5 (8)
C19—C20—C21—C22−178.0 (6)O1—Cu1—N4—C58.5 (4)
C20—C21—C22—C23−3.2 (10)Cl4—Cu1—N4—C5−164.5 (4)
C21—C22—C23—C242.7 (10)N3—Cu1—N4—C1−180.0 (5)
C22—C23—C24—N10.3 (10)O1—Cu1—N4—C1−170.9 (5)
C21—C20—N1—C242.1 (8)Cl4—Cu1—N4—C116.1 (5)
C19—C20—N1—C24−179.0 (5)C8—C7—O1—C6−161.6 (4)
C21—C20—N1—Cu2−177.1 (4)C8—C7—O1—Cu1−21.1 (6)
C19—C20—N1—Cu21.8 (6)C5—C6—O1—C7163.5 (4)
C23—C24—N1—C20−2.7 (8)C5—C6—O1—Cu123.1 (5)
C23—C24—N1—Cu2176.4 (4)N3—Cu1—O1—C717.4 (4)
N2—Cu2—N1—C2012.5 (8)N4—Cu1—O1—C7−159.8 (4)
O2—Cu2—N1—C20−9.0 (4)Cl4—Cu1—O1—C7−70.6 (10)
Cl3—Cu2—N1—C20156.7 (4)N3—Cu1—O1—C6158.8 (4)
O11—Cu2—N1—C20−97.2 (4)N4—Cu1—O1—C6−18.4 (4)
N2—Cu2—N1—C24−166.6 (5)Cl4—Cu1—O1—C670.8 (11)
O2—Cu2—N1—C24171.8 (5)C20—C19—O2—C18−158.7 (5)
Cl3—Cu2—N1—C24−22.4 (5)C20—C19—O2—Cu2−17.4 (6)
O11—Cu2—N1—C2483.7 (5)C17—C18—O2—C19159.6 (5)
C16—C17—N2—C14−0.5 (8)C17—C18—O2—Cu218.0 (6)
C18—C17—N2—C14179.8 (5)N2—Cu2—O2—C19−157.4 (4)
C16—C17—N2—Cu2179.3 (4)N1—Cu2—O2—C1915.3 (4)
C18—C17—N2—Cu2−0.4 (7)Cl3—Cu2—O2—C19−69.9 (6)
C13—C14—N2—C170.6 (9)O11—Cu2—O2—C19108.5 (4)
C13—C14—N2—Cu2−179.1 (5)N2—Cu2—O2—C18−15.2 (4)
N1—Cu2—N2—C17−13.2 (8)N1—Cu2—O2—C18157.4 (4)
O2—Cu2—N2—C178.4 (4)Cl3—Cu2—O2—C1872.2 (6)
Cl3—Cu2—N2—C17−157.4 (4)O11—Cu2—O2—C18−109.4 (4)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O11—H11A···O5i0.902.052.725 (8)131
O11—H11B···O9ii0.901.922.787 (10)163

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH2860).

References

  • Bruker (1997). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Li, J. M. (2007). Acta Cryst. E63, m2241. [PMC free article] [PubMed]
  • Li, J. M. (2008a). Acta Cryst. E64, m1467. [PMC free article] [PubMed]
  • Li, J. (2008b). Acta Cryst. E64, m1468. [PMC free article] [PubMed]
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]

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