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Acta Crystallogr Sect E Struct Rep Online. 2010 October 1; 66(Pt 10): m1201–m1202.
Published online 2010 September 4. doi:  10.1107/S1600536810034513
PMCID: PMC2983384

[μ-N,N,N′,N′-Tetra­kis­(2-pyridyl­meth­yl)pentane-1,5-diamine]­bis­[dichlorido­copper(II)] sesquihydrate

Abstract

In the title dinuclear copper complex, [Cu2Cl4(C29H34N6)]·1.5H2O, both CuII ions are coordinated in a slightly distorted square-pyramidal environment in which the N atoms of the dipicolyl­amine group and a chloride ligand form the basal plane. The apical position is occupied by a second chloride atom. The Cu—N distances involving the pyridine N atoms differ slightly from each other and the Cu—N distance involving the tertiary N atom is the longest. The apical Cu—Cl distance is elongated compared to its basal counterpart due to typical Jahn–Teller distortion. In the crystal structure, complex and water mol­ecules are linked via inter­molecular O—H(...)O and O—H(...)Cl hydrogen bonds into chains along [001]. One of the water mol­ecules was refined with half occupancy.

Related literature

For crystallographic data of tetra­kis­(pyridin-2-yl-meth­yl)alkyl-diamines, see: Fujihara et al. (2004 [triangle]); Mambanda et al. (2007 [triangle]). For the superoxide dismutase activity of iron complexes, see: Tamura et al. (2000 [triangle]). For dinuclear Pt complexes of similar ligands, see: Ertürk et al. (2007 [triangle]). For the use of the dipicolyl­amine moiety for binding of the M(CO)3 core (M = Re, 99mTc), see: Bartholomä et al. (2009 [triangle]). For crystal structures closely related to the title compound, see: Bartholomä et al. (2010a [triangle],b [triangle],c [triangle],d [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-m1201-scheme1.jpg

Experimental

Crystal data

  • [Cu2Cl4(C29H34N6)]·1.5H2O
  • M r = 762.55
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-m1201-efi1.jpg
  • a = 8.2003 (13) Å
  • b = 14.3700 (16) Å
  • c = 27.688 (4) Å
  • β = 97.919 (6)°
  • V = 3231.6 (8) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 1.68 mm−1
  • T = 90 K
  • 0.22 × 0.16 × 0.12 mm

Data collection

  • Bruker APEX CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.709, T max = 0.824
  • 31227 measured reflections
  • 7827 independent reflections
  • 7421 reflections with I > 2σ(I)
  • R int = 0.050

Refinement

  • R[F 2 > 2σ(F 2)] = 0.079
  • wR(F 2) = 0.156
  • S = 1.40
  • 7827 reflections
  • 404 parameters
  • 5 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.81 e Å−3
  • Δρmin = −0.67 e Å−3

Data collection: SMART (Bruker, 2002 [triangle]); cell refinement: SAINT (Bruker, 2002 [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: DIAMOND (Brandenburg & Putz, 1999 [triangle]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 [triangle]).

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

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810034513/lh5109sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810034513/lh5109Isup2.hkl

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

Acknowledgments

This work was supported by funding from Syracuse University.

supplementary crystallographic information

Comment

The described ligand has been used as starting material for hydrothermal synthesis of metal-organic transition metal/molybdateoxide frameworks in the principal author's laboratory (Bartholomä, unpublished results). The dipicolylamine moiety has originally been developed in our laboratory as metal chelating entity for binding of the M(CO)3 core (M = Re,99mTc) for radiopharmaceutical purposes. However, a different coordination mode has been observed for the M(CO)3 core in which the dipicolylamine metal chelate is coordinated in a facial manner (Bartholomä, 2009).

The title complex was prepared as part of a series with different cadmium and copper salts to study the coordination properties of the ligand with these metals without the interaction of metaloxide clusters (Bartholomä, 2010a,b,d). The shorter homologue N1,N1,N4,N4-tetrakis(pyridin-2-ylmethyl)butane-1,4-diamine gave structurally similar complexes with copper bromide as metal salt. The corresponding Cu—Npy distances are 2.015 (6) Å and 2.019 (6) Å and the Cu—Ntert distance was determined to 2.053 (5) Å (Bartholomä, 2010c).

Crystal structures of the ligands N1,N1,N3,N3-tetrakis(2-pyridiniomethyl)-1,3-diaminopropane and N1,N1,N4,N4-tetrakis(pyridin-2-ylmethyl)butane-1,4-diamine have been described recently (Fujihara, 2004; Mambanda, 2007). Superoxide dismutase activity of iron(II) complexes of N1,N1,N3,N3-tetrakis(2-pyridiniomethyl)-1,3-diaminopropane and related ligands has been investigated by Tamura et al. (2000). Studies on the thermodynamic and kinetic behaviour of the reaction of platinum(II) complexes of higher ligand homologues with chloride have been performed by Ertürk et al. (2007).

Experimental

N1,N1,N5,N5-tetrakis(pyridin-2-ylmethyl)pentane-1,5-diamine. An amount of 1.00 g (9.78 mmol) 1,5-diaminopentane was dissolved in 30 ml anhydrous dichloroethane under an inert atmosphere (argon) followed by the addition of 3.91 ml (41.10 mmol) pyridine-2-carboxaldehyde. The mixture was stirred for 15 min at r.t. and then cooled with an ice bath prior to the portionwise addition of 12.44 g (58.72 mmol) sodium triacetoxyborohydride (gas evolution, exothermic reaction). The reaction was stirred overnight allowing the temperature slowly to rise to room temperature. The reaction was quenched by the dropwise addition of saturated sodium bicarbonate solution and stirring was continued until the gas evolution ceased. The mixture was separated and the organic layer was further washed with saturated sodium bicarbonate solution, water and brine. The organic phase was dried with anhydrous sodium sulfate, filtered and the solvent removed under reduced pressure. The crude reaction mixture was then purified by silica gel column chromatography starting with chloroform and increasing gradient to chloroform:methanol 10:1 (v/v). Yield: 4.02 g (86%). 1H NMR (CDCl3): δ = 8.39 (m, 4H), 7.49 (m, 4H), 7.37 (d, J = 7.81 Hz, 4H), 6.95 (m, 4H), 3.64 (s, 8H), 2.36 (m, 4H), 1.33 (m, 4H), 1.07 (m, 2H) p.p.m..

Synthesis of metal complex. To 2 ml of an aqueous solution of copper chloride, two equivalents (50 mg, 0.11 mmol) of N1,N1,N5,N5-tetrakis(pyridin-2-ylmethyl)pentane-1,5-diamine in 2 ml methanol were added followed by the addition of 2 ml N,N-dimethylformamide. Single crystals were obtained after a week by slow evaporation of the solvents at room temperature.

Refinement

All the H atoms were placed in idealized positions and refined by the riding model approximation with C—Haryl = 0.95 Å, C—Hmethyl = 0.98Å and C—Hmethylene = 0.99Åand Uiso(H) = 1.5Ueq(Cmethyl) and 1.2Ueq(Cmethylene/aryl). Water hydrogen atoms were initially located in the difference Fourier map but were then refined with O—H = 0.84 (2) Å and Uiso(H) = 1.5 Ueq(O).

Figures

Fig. 1.
The molecular structure of the title complex. The displacement ellipsoids are drawn at 50% probability level. solvent water molecules and hydrogen atoms are omitted for clarity.

Crystal data

[Cu2Cl4(C29H34N6)]·1.5H2OF(000) = 1564
Mr = 762.55Dx = 1.561 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 6480 reflections
a = 8.2003 (13) Åθ = 5.3–56.1°
b = 14.3700 (16) ŵ = 1.68 mm1
c = 27.688 (4) ÅT = 90 K
β = 97.919 (6)°Neeldes, blue
V = 3231.6 (8) Å30.22 × 0.16 × 0.12 mm
Z = 4

Data collection

Bruker APEX CCD diffractometer7827 independent reflections
Radiation source: fine-focus sealed tube7421 reflections with I > 2σ(I)
graphiteRint = 0.050
Detector resolution: 512 pixels mm-1θmax = 28.1°, θmin = 1.6°
[var phi] and ω scansh = −10→10
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)k = −18→18
Tmin = 0.709, Tmax = 0.824l = −36→35
31227 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)] = 0.079Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.156H atoms treated by a mixture of independent and constrained refinement
S = 1.40w = 1/[σ2(Fo2) + (0.0289P)2 + 16.2006P] where P = (Fo2 + 2Fc2)/3
7827 reflections(Δ/σ)max = 0.003
404 parametersΔρmax = 0.81 e Å3
5 restraintsΔρmin = −0.67 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)
Cu10.27113 (7)0.72996 (4)1.01183 (2)0.01076 (13)
Cu20.27749 (7)0.33032 (4)0.71531 (2)0.01413 (14)
Cl10.18034 (14)0.87113 (8)1.05552 (4)0.0141 (2)
Cl20.37112 (16)0.61583 (9)1.06521 (5)0.0213 (3)
Cl30.41385 (17)0.36546 (10)0.65260 (5)0.0258 (3)
Cl40.10401 (16)0.18600 (9)0.69447 (5)0.0215 (3)
O10.2269 (9)0.9799 (4)0.6606 (2)0.0570 (16)
O20.9605 (10)0.2886 (6)0.8770 (3)0.0253 (17)0.50
N10.4863 (5)0.7920 (3)1.00962 (14)0.0113 (8)
N20.2270 (5)0.7828 (3)0.94143 (14)0.0114 (8)
N30.0433 (5)0.6801 (3)0.99475 (15)0.0120 (8)
N40.4603 (5)0.2609 (3)0.75526 (15)0.0159 (8)
N50.2081 (5)0.3520 (3)0.78308 (15)0.0132 (8)
N60.0870 (5)0.4163 (3)0.69621 (15)0.0168 (9)
C10.3151 (6)0.8723 (3)0.94483 (17)0.0114 (9)
H1A0.24950.91990.95940.014*
H1B0.33150.89370.91180.014*
C20.4794 (6)0.8601 (3)0.97598 (17)0.0140 (9)
C30.6144 (6)0.9175 (3)0.97175 (19)0.0158 (10)
H30.60750.96570.94800.019*
C40.7587 (6)0.9022 (4)1.0032 (2)0.0190 (11)
H40.85260.94011.00120.023*
C50.7659 (6)0.8316 (4)1.03749 (19)0.0180 (10)
H50.86420.82011.05910.022*
C60.6271 (6)0.7785 (3)1.03951 (18)0.0156 (9)
H60.63140.73021.06310.019*
C70.0454 (6)0.7921 (3)0.92979 (17)0.0131 (9)
H7A0.01320.78870.89400.016*
H7B0.01080.85350.94110.016*
C8−0.0398 (6)0.7164 (3)0.95395 (17)0.0132 (9)
C9−0.1994 (6)0.6872 (3)0.93578 (17)0.0141 (9)
H9−0.25570.71320.90660.017*
C10−0.2733 (6)0.6204 (3)0.96078 (19)0.0169 (10)
H10−0.38120.59920.94900.020*
C11−0.1882 (6)0.5841 (4)1.0036 (2)0.0199 (11)
H11−0.23820.53881.02180.024*
C12−0.0301 (6)0.6148 (3)1.01933 (19)0.0175 (10)
H120.02860.58921.04830.021*
C130.2943 (6)0.7235 (3)0.90419 (17)0.0128 (9)
H13A0.41600.72650.91030.015*
H13B0.25900.75060.87160.015*
C140.2430 (6)0.6220 (3)0.90307 (16)0.0129 (9)
H14A0.12150.61730.89920.016*
H14B0.28800.59150.93410.016*
C150.3081 (6)0.5735 (4)0.86064 (19)0.0172 (10)
H15A0.42980.57110.86730.021*
H15B0.27800.61090.83070.021*
C160.2422 (6)0.4749 (3)0.85142 (18)0.0165 (10)
H16A0.12110.47460.85040.020*
H16B0.29020.43340.87820.020*
C170.2879 (6)0.4396 (3)0.80292 (17)0.0147 (9)
H17A0.26110.48910.77830.018*
H17B0.40860.43030.80690.018*
C180.2662 (6)0.2696 (3)0.81311 (18)0.0161 (10)
H18A0.18720.21760.80610.019*
H18B0.27380.28510.84820.019*
C190.4314 (6)0.2415 (3)0.80118 (18)0.0155 (9)
C200.5471 (7)0.1945 (4)0.8336 (2)0.0222 (11)
H200.52770.18380.86620.027*
C210.6906 (7)0.1636 (4)0.8181 (2)0.0268 (12)
H210.77020.13060.83970.032*
C220.7170 (7)0.1812 (4)0.7709 (2)0.0218 (11)
H220.81360.15900.75930.026*
C230.6002 (7)0.2317 (4)0.74057 (19)0.0207 (11)
H230.62040.24600.70840.025*
C240.0260 (6)0.3601 (4)0.77349 (19)0.0181 (10)
H24A−0.01550.38990.80170.022*
H24B−0.02390.29740.76890.022*
C25−0.0214 (6)0.4176 (4)0.72845 (19)0.0192 (10)
C26−0.1696 (7)0.4657 (4)0.7199 (2)0.0241 (12)
H26−0.24520.46490.74300.029*
C27−0.2036 (7)0.5149 (4)0.6766 (2)0.0301 (14)
H27−0.30530.54700.66920.036*
C28−0.0899 (8)0.5172 (4)0.6444 (2)0.0274 (13)
H28−0.10990.55270.61520.033*
C290.0536 (7)0.4668 (4)0.6552 (2)0.0225 (11)
H290.13180.46800.63290.027*
H1WA0.208 (14)1.035 (3)0.668 (4)0.10 (4)*
H1WB0.266 (9)0.972 (6)0.6345 (17)0.05 (2)*
H2WA0.889 (10)0.330 (5)0.871 (5)0.04 (4)*0.50
H2WB0.904 (10)0.242 (4)0.882 (4)0.02 (3)*0.50

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cu10.0096 (3)0.0114 (3)0.0112 (3)−0.0016 (2)0.0012 (2)0.0018 (2)
Cu20.0172 (3)0.0144 (3)0.0109 (3)0.0015 (2)0.0023 (2)−0.0014 (2)
Cl10.0143 (5)0.0144 (5)0.0144 (5)−0.0022 (4)0.0044 (4)−0.0035 (4)
Cl20.0212 (6)0.0173 (6)0.0238 (6)−0.0021 (5)−0.0028 (5)0.0082 (5)
Cl30.0299 (7)0.0301 (7)0.0190 (6)0.0026 (6)0.0094 (5)0.0040 (5)
Cl40.0265 (6)0.0175 (6)0.0198 (6)−0.0050 (5)0.0003 (5)−0.0031 (5)
O10.085 (4)0.037 (3)0.060 (4)−0.001 (3)0.052 (3)−0.002 (3)
O20.023 (4)0.025 (4)0.028 (4)−0.002 (3)0.006 (3)0.005 (3)
N10.0084 (17)0.0120 (19)0.0145 (19)0.0006 (14)0.0053 (14)−0.0030 (15)
N20.0122 (18)0.0108 (19)0.0111 (18)−0.0029 (15)0.0020 (14)−0.0013 (14)
N30.0131 (18)0.0085 (18)0.0154 (19)−0.0025 (14)0.0052 (15)−0.0003 (15)
N40.016 (2)0.014 (2)0.018 (2)−0.0005 (16)0.0032 (16)−0.0031 (16)
N50.0125 (19)0.013 (2)0.0141 (19)0.0033 (15)0.0028 (15)0.0014 (15)
N60.019 (2)0.018 (2)0.013 (2)−0.0027 (17)−0.0012 (16)−0.0039 (16)
C10.014 (2)0.009 (2)0.012 (2)−0.0028 (17)0.0033 (17)−0.0009 (16)
C20.015 (2)0.014 (2)0.014 (2)−0.0013 (18)0.0048 (18)−0.0079 (18)
C30.016 (2)0.011 (2)0.023 (3)−0.0052 (18)0.0107 (19)−0.0044 (19)
C40.014 (2)0.016 (2)0.029 (3)−0.0032 (19)0.009 (2)−0.015 (2)
C50.008 (2)0.025 (3)0.021 (2)0.0015 (19)0.0016 (18)−0.011 (2)
C60.016 (2)0.015 (2)0.016 (2)0.0001 (18)0.0032 (18)−0.0042 (18)
C70.012 (2)0.014 (2)0.013 (2)0.0003 (17)0.0014 (17)−0.0003 (17)
C80.017 (2)0.009 (2)0.015 (2)0.0028 (17)0.0069 (18)−0.0032 (17)
C90.013 (2)0.016 (2)0.013 (2)0.0010 (18)0.0013 (17)−0.0034 (18)
C100.015 (2)0.014 (2)0.022 (3)0.0006 (18)0.0024 (19)−0.0023 (19)
C110.017 (2)0.014 (2)0.031 (3)−0.0026 (19)0.011 (2)0.004 (2)
C120.020 (2)0.014 (2)0.019 (2)0.0021 (19)0.0026 (19)0.0045 (19)
C130.013 (2)0.013 (2)0.013 (2)−0.0025 (17)0.0019 (17)−0.0034 (17)
C140.018 (2)0.014 (2)0.008 (2)−0.0015 (18)0.0043 (17)−0.0011 (17)
C150.019 (2)0.016 (2)0.018 (2)−0.0020 (19)0.0085 (19)−0.0039 (19)
C160.023 (3)0.014 (2)0.013 (2)−0.0006 (19)0.0070 (19)−0.0024 (18)
C170.017 (2)0.015 (2)0.011 (2)−0.0003 (18)0.0002 (18)−0.0008 (18)
C180.024 (2)0.011 (2)0.014 (2)0.0023 (19)0.0052 (19)0.0036 (18)
C190.022 (2)0.010 (2)0.015 (2)0.0001 (18)0.0014 (19)−0.0010 (18)
C200.030 (3)0.019 (3)0.017 (2)0.003 (2)0.000 (2)0.001 (2)
C210.026 (3)0.025 (3)0.027 (3)0.008 (2)−0.004 (2)0.001 (2)
C220.018 (2)0.019 (3)0.028 (3)0.001 (2)0.003 (2)−0.009 (2)
C230.024 (3)0.021 (3)0.018 (2)−0.004 (2)0.007 (2)−0.008 (2)
C240.015 (2)0.018 (2)0.021 (3)0.0002 (19)0.0017 (19)−0.002 (2)
C250.020 (2)0.014 (2)0.022 (3)−0.001 (2)−0.002 (2)−0.003 (2)
C260.018 (3)0.017 (3)0.036 (3)0.002 (2)−0.001 (2)−0.004 (2)
C270.028 (3)0.016 (3)0.044 (4)0.009 (2)−0.006 (3)−0.005 (2)
C280.038 (3)0.015 (3)0.025 (3)0.000 (2)−0.007 (2)0.000 (2)
C290.030 (3)0.016 (2)0.020 (3)−0.005 (2)−0.001 (2)−0.003 (2)

Geometric parameters (Å, °)

Cu1—N11.986 (4)C9—C101.372 (7)
Cu1—N31.996 (4)C9—H90.9500
Cu1—N22.076 (4)C10—C111.392 (7)
Cu1—Cl22.2832 (13)C10—H100.9500
Cu1—Cl12.5261 (13)C11—C121.382 (7)
Cu2—N42.002 (4)C11—H110.9500
Cu2—N62.005 (4)C12—H120.9500
Cu2—N52.058 (4)C13—C141.517 (6)
Cu2—Cl32.2484 (14)C13—H13A0.9900
Cu2—Cl42.5361 (14)C13—H13B0.9900
O1—H1WA0.84 (2)C14—C151.524 (6)
O1—H1WB0.84 (2)C14—H14A0.9900
O2—H2WA0.84 (2)C14—H14B0.9900
O2—H2WB0.83 (2)C15—C161.525 (7)
N1—C61.339 (6)C15—H15A0.9900
N1—C21.346 (6)C15—H15B0.9900
N2—C11.473 (6)C16—C171.529 (7)
N2—C71.486 (6)C16—H16A0.9900
N2—C131.500 (6)C16—H16B0.9900
N3—C81.342 (6)C17—H17A0.9900
N3—C121.348 (6)C17—H17B0.9900
N4—C231.337 (7)C18—C191.494 (7)
N4—C191.354 (6)C18—H18A0.9900
N5—C241.485 (6)C18—H18B0.9900
N5—C171.487 (6)C19—C201.388 (7)
N5—C181.488 (6)C20—C211.381 (8)
N6—C291.343 (7)C20—H200.9500
N6—C251.344 (7)C21—C221.376 (8)
C1—C21.507 (6)C21—H210.9500
C1—H1A0.9900C22—C231.389 (8)
C1—H1B0.9900C22—H220.9500
C2—C31.399 (7)C23—H230.9500
C3—C41.386 (7)C24—C251.502 (7)
C3—H30.9500C24—H24A0.9900
C4—C51.386 (8)C24—H24B0.9900
C4—H40.9500C25—C261.390 (7)
C5—C61.378 (7)C26—C271.387 (9)
C5—H50.9500C26—H260.9500
C6—H60.9500C27—C281.377 (9)
C7—C81.499 (7)C27—H270.9500
C7—H7A0.9900C28—C291.379 (8)
C7—H7B0.9900C28—H280.9500
C8—C91.400 (7)C29—H290.9500
N1—Cu1—N3163.88 (16)C9—C10—H10120.4
N1—Cu1—N281.22 (16)C11—C10—H10120.4
N3—Cu1—N282.68 (16)C12—C11—C10119.1 (5)
N1—Cu1—Cl295.81 (12)C12—C11—H11120.4
N3—Cu1—Cl297.84 (12)C10—C11—H11120.4
N2—Cu1—Cl2150.55 (12)N3—C12—C11121.9 (5)
N1—Cu1—Cl188.61 (11)N3—C12—H12119.1
N3—Cu1—Cl194.23 (12)C11—C12—H12119.1
N2—Cu1—Cl197.55 (11)N2—C13—C14115.7 (4)
Cl2—Cu1—Cl1111.72 (5)N2—C13—H13A108.4
N4—Cu2—N6161.75 (17)C14—C13—H13A108.4
N4—Cu2—N581.47 (16)N2—C13—H13B108.4
N6—Cu2—N581.02 (16)C14—C13—H13B108.4
N4—Cu2—Cl397.15 (13)H13A—C13—H13B107.4
N6—Cu2—Cl396.33 (13)C13—C14—C15109.3 (4)
N5—Cu2—Cl3154.07 (13)C13—C14—H14A109.8
N4—Cu2—Cl494.14 (13)C15—C14—H14A109.8
N6—Cu2—Cl492.95 (13)C13—C14—H14B109.8
N5—Cu2—Cl496.58 (12)C15—C14—H14B109.8
Cl3—Cu2—Cl4109.33 (5)H14A—C14—H14B108.3
H1WA—O1—H1WB117 (9)C14—C15—C16113.6 (4)
H2WA—O2—H2WB102 (3)C14—C15—H15A108.8
C6—N1—C2118.9 (4)C16—C15—H15A108.8
C6—N1—Cu1127.6 (3)C14—C15—H15B108.8
C2—N1—Cu1113.3 (3)C16—C15—H15B108.8
C1—N2—C7113.8 (4)H15A—C15—H15B107.7
C1—N2—C13108.5 (4)C15—C16—C17109.4 (4)
C7—N2—C13110.8 (3)C15—C16—H16A109.8
C1—N2—Cu1103.8 (3)C17—C16—H16A109.8
C7—N2—Cu1106.0 (3)C15—C16—H16B109.8
C13—N2—Cu1113.9 (3)C17—C16—H16B109.8
C8—N3—C12119.0 (4)H16A—C16—H16B108.2
C8—N3—Cu1114.2 (3)N5—C17—C16117.2 (4)
C12—N3—Cu1126.8 (3)N5—C17—H17A108.0
C23—N4—C19119.3 (4)C16—C17—H17A108.0
C23—N4—Cu2126.7 (4)N5—C17—H17B108.0
C19—N4—Cu2114.0 (3)C16—C17—H17B108.0
C24—N5—C17112.4 (4)H17A—C17—H17B107.2
C24—N5—C18113.5 (4)N5—C18—C19108.8 (4)
C17—N5—C18112.1 (4)N5—C18—H18A109.9
C24—N5—Cu2104.3 (3)C19—C18—H18A109.9
C17—N5—Cu2107.6 (3)N5—C18—H18B109.9
C18—N5—Cu2106.4 (3)C19—C18—H18B109.9
C29—N6—C25118.5 (5)H18A—C18—H18B108.3
C29—N6—Cu2128.1 (4)N4—C19—C20121.0 (5)
C25—N6—Cu2113.3 (3)N4—C19—C18115.7 (4)
N2—C1—C2109.1 (4)C20—C19—C18123.2 (5)
N2—C1—H1A109.9C21—C20—C19119.4 (5)
C2—C1—H1A109.9C21—C20—H20120.3
N2—C1—H1B109.9C19—C20—H20120.3
C2—C1—H1B109.9C22—C21—C20119.3 (5)
H1A—C1—H1B108.3C22—C21—H21120.4
N1—C2—C3121.9 (5)C20—C21—H21120.4
N1—C2—C1115.4 (4)C21—C22—C23119.0 (5)
C3—C2—C1122.6 (5)C21—C22—H22120.5
C4—C3—C2118.1 (5)C23—C22—H22120.5
C4—C3—H3121.0N4—C23—C22122.0 (5)
C2—C3—H3121.0N4—C23—H23119.0
C5—C4—C3119.9 (5)C22—C23—H23119.0
C5—C4—H4120.1N5—C24—C25109.3 (4)
C3—C4—H4120.1N5—C24—H24A109.8
C6—C5—C4118.4 (5)C25—C24—H24A109.8
C6—C5—H5120.8N5—C24—H24B109.8
C4—C5—H5120.8C25—C24—H24B109.8
N1—C6—C5122.7 (5)H24A—C24—H24B108.3
N1—C6—H6118.6N6—C25—C26122.5 (5)
C5—C6—H6118.6N6—C25—C24115.1 (4)
N2—C7—C8110.7 (4)C26—C25—C24122.4 (5)
N2—C7—H7A109.5C27—C26—C25117.9 (6)
C8—C7—H7A109.5C27—C26—H26121.0
N2—C7—H7B109.5C25—C26—H26121.0
C8—C7—H7B109.5C28—C27—C26119.9 (5)
H7A—C7—H7B108.1C28—C27—H27120.0
N3—C8—C9121.8 (4)C26—C27—H27120.0
N3—C8—C7116.3 (4)C27—C28—C29118.7 (5)
C9—C8—C7121.8 (4)C27—C28—H28120.7
C10—C9—C8119.0 (5)C29—C28—H28120.7
C10—C9—H9120.5N6—C29—C28122.5 (5)
C8—C9—H9120.5N6—C29—H29118.8
C9—C10—C11119.2 (5)C28—C29—H29118.8
N3—Cu1—N1—C6−160.7 (5)N1—C2—C3—C40.6 (7)
N2—Cu1—N1—C6−163.3 (4)C1—C2—C3—C4178.1 (4)
Cl2—Cu1—N1—C6−12.9 (4)C2—C3—C4—C50.0 (7)
Cl1—Cu1—N1—C698.8 (4)C3—C4—C5—C6−0.4 (7)
N3—Cu1—N1—C225.0 (8)C2—N1—C6—C50.2 (7)
N2—Cu1—N1—C222.3 (3)Cu1—N1—C6—C5−173.8 (4)
Cl2—Cu1—N1—C2172.8 (3)C4—C5—C6—N10.3 (7)
Cl1—Cu1—N1—C2−75.5 (3)C1—N2—C7—C8−147.0 (4)
N1—Cu1—N2—C1−35.2 (3)C13—N2—C7—C890.5 (4)
N3—Cu1—N2—C1145.6 (3)Cu1—N2—C7—C8−33.5 (4)
Cl2—Cu1—N2—C1−121.5 (3)C12—N3—C8—C9−1.1 (7)
Cl1—Cu1—N2—C152.2 (3)Cu1—N3—C8—C9178.0 (3)
N1—Cu1—N2—C7−155.4 (3)C12—N3—C8—C7177.0 (4)
N3—Cu1—N2—C725.4 (3)Cu1—N3—C8—C7−3.9 (5)
Cl2—Cu1—N2—C7118.4 (3)N2—C7—C8—N326.3 (6)
Cl1—Cu1—N2—C7−68.0 (3)N2—C7—C8—C9−155.6 (4)
N1—Cu1—N2—C1382.6 (3)N3—C8—C9—C100.8 (7)
N3—Cu1—N2—C13−96.7 (3)C7—C8—C9—C10−177.2 (4)
Cl2—Cu1—N2—C13−3.7 (4)C8—C9—C10—C110.5 (7)
Cl1—Cu1—N2—C13170.0 (3)C9—C10—C11—C12−1.4 (8)
N1—Cu1—N3—C8−15.3 (8)C8—N3—C12—C110.2 (7)
N2—Cu1—N3—C8−12.7 (3)Cu1—N3—C12—C11−178.8 (4)
Cl2—Cu1—N3—C8−162.9 (3)C10—C11—C12—N31.1 (8)
Cl1—Cu1—N3—C884.4 (3)C1—N2—C13—C14168.1 (4)
N1—Cu1—N3—C12163.7 (5)C7—N2—C13—C14−66.4 (5)
N2—Cu1—N3—C12166.4 (4)Cu1—N2—C13—C1453.0 (5)
Cl2—Cu1—N3—C1216.1 (4)N2—C13—C14—C15174.9 (4)
Cl1—Cu1—N3—C12−96.6 (4)C13—C14—C15—C16−171.3 (4)
N6—Cu2—N4—C23−149.6 (5)C14—C15—C16—C17169.4 (4)
N5—Cu2—N4—C23−166.1 (4)C24—N5—C17—C1660.6 (5)
Cl3—Cu2—N4—C23−12.3 (4)C18—N5—C17—C16−68.6 (5)
Cl4—Cu2—N4—C2397.8 (4)Cu2—N5—C17—C16174.8 (3)
N6—Cu2—N4—C1932.0 (7)C15—C16—C17—N5−168.8 (4)
N5—Cu2—N4—C1915.5 (3)C24—N5—C18—C19153.0 (4)
Cl3—Cu2—N4—C19169.4 (3)C17—N5—C18—C19−78.4 (5)
Cl4—Cu2—N4—C19−80.6 (3)Cu2—N5—C18—C1939.0 (4)
N4—Cu2—N5—C24−150.3 (3)C23—N4—C19—C202.2 (7)
N6—Cu2—N5—C2434.9 (3)Cu2—N4—C19—C20−179.3 (4)
Cl3—Cu2—N5—C24120.9 (3)C23—N4—C19—C18−175.0 (4)
Cl4—Cu2—N5—C24−57.0 (3)Cu2—N4—C19—C183.5 (5)
N4—Cu2—N5—C1790.3 (3)N5—C18—C19—N4−29.2 (6)
N6—Cu2—N5—C17−84.6 (3)N5—C18—C19—C20153.7 (5)
Cl3—Cu2—N5—C171.5 (5)N4—C19—C20—C21−2.9 (8)
Cl4—Cu2—N5—C17−176.5 (3)C18—C19—C20—C21174.0 (5)
N4—Cu2—N5—C18−30.1 (3)C19—C20—C21—C220.9 (9)
N6—Cu2—N5—C18155.1 (3)C20—C21—C22—C231.7 (8)
Cl3—Cu2—N5—C18−118.9 (3)C19—N4—C23—C220.5 (8)
Cl4—Cu2—N5—C1863.2 (3)Cu2—N4—C23—C22−177.8 (4)
N4—Cu2—N6—C29144.3 (5)C21—C22—C23—N4−2.5 (8)
N5—Cu2—N6—C29160.9 (5)C17—N5—C24—C2574.5 (5)
Cl3—Cu2—N6—C296.9 (4)C18—N5—C24—C25−157.0 (4)
Cl4—Cu2—N6—C29−102.9 (4)Cu2—N5—C24—C25−41.7 (4)
N4—Cu2—N6—C25−39.2 (7)C29—N6—C25—C263.1 (7)
N5—Cu2—N6—C25−22.6 (3)Cu2—N6—C25—C26−173.8 (4)
Cl3—Cu2—N6—C25−176.6 (3)C29—N6—C25—C24−179.3 (4)
Cl4—Cu2—N6—C2573.6 (3)Cu2—N6—C25—C243.8 (5)
C7—N2—C1—C2156.6 (4)N5—C24—C25—N626.7 (6)
C13—N2—C1—C2−79.7 (4)N5—C24—C25—C26−155.7 (5)
Cu1—N2—C1—C241.8 (4)N6—C25—C26—C27−1.0 (8)
C6—N1—C2—C3−0.7 (7)C24—C25—C26—C27−178.4 (5)
Cu1—N1—C2—C3174.2 (4)C25—C26—C27—C28−1.9 (8)
C6—N1—C2—C1−178.3 (4)C26—C27—C28—C292.6 (8)
Cu1—N1—C2—C1−3.5 (5)C25—N6—C29—C28−2.3 (8)
N2—C1—C2—N1−27.4 (5)Cu2—N6—C29—C28174.0 (4)
N2—C1—C2—C3154.9 (4)C27—C28—C29—N6−0.5 (8)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O2—H2WB···Cl1i0.83 (2)2.54 (7)3.270 (8)147 (11)
O2—H2WA···O1ii0.84 (2)2.46 (4)3.249 (11)157 (10)
O1—H1WB···Cl2iii0.84 (2)2.54 (4)3.335 (6)159 (8)
O1—H1WA···Cl4iv0.84 (2)2.47 (3)3.306 (6)169 (10)

Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) −x+1, y−1/2, −z+3/2; (iii) x, −y+3/2, z−1/2; (iv) x, y+1, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5109).

References

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