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The dinuclear title complex, [Cu2(C46H38N4O2)Cl2]·0.5C2H5OH·2H2O, is located on crystallographic inversion centres with two half-mol­ecules in the asymmetric unit. The two CuII atoms are coordinated by a hexa­dentate dianionic ligand formed in situ from the condensation of two tridentate ligands by four imine N atoms and two bridging phenolate O atoms along with two Cl atoms at axial positions. The coordination geometry around the metal atoms is distorted square-pyramidal (τ = 0.185 and 0.199). The non-bonding Cu...Cu distances are 2.9556 (12) and 2.9506 (12) Å in the two dimers. The packing is stabilized through solvent-mediated inter­molecular O—H...O and O—H...Cl hydrogen bonds. The diamine chain of one of the dimers is disordered over two positions in a 0.680 (5):0.320 (5) ratio.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536810042248/bt5381sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536810042248/bt5381Isup2.hkl
Contains datablock I

CCDC reference: 802965

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • Some non-H atoms missing
  • Disorder in main residue
  • R factor = 0.044
  • wR factor = 0.137
  • Data-to-parameter ratio = 11.6

checkCIF/PLATON results

No syntax errors found



Alert level A ABSMU01_ALERT_1_A The ratio of given/expected absorption coefficient lies outside the range 0.90 <> 1.10 Calculated value of mu = 0.539 Value of mu given = 1.079 CHEMW03_ALERT_2_A ALERT: The ratio of given/expected molecular weight as calculated from the _atom_site* data lies outside the range 0.90 <> 1.10 From the CIF: _cell_formula_units_Z 2 From the CIF: _chemical_formula_weight 935.85 TEST: Calculate formula weight from _atom_site_* atom mass num sum C 12.01 94.00 1129.03 H 1.01 90.00 90.72 N 14.01 8.00 112.06 O 16.00 9.00 143.99 Cl 35.45 4.00 141.81 Cu 63.55 4.00 254.18 Calculated formula weight 1871.80 DENSD01_ALERT_1_A The ratio of the submitted crystal density and that calculated from the formula is outside the range 0.90 <> 1.10 Crystal density given = 1.340 Calculated crystal density = 0.670 PLAT043_ALERT_1_A Check Reported Molecular Weight ................ 935.85 PLAT046_ALERT_1_A Reported Z, MW and D(calc) are Inconsistent .... 0.67
Alert level B THETM01_ALERT_3_B The value of sine(theta_max)/wavelength is less than 0.575 Calculated sin(theta_max)/wavelength = 0.5570 PLAT023_ALERT_3_B Resolution (too) Low [sin(theta)/Lambda < 0.6].. 23.32 Deg.
Alert level C PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Cu2 -- Cl2 .. 7.99 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Cu1 -- Cl1 .. 9.11 su PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C15 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for Cu2 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for Cu1 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.09 PLAT331_ALERT_2_C Small Average Phenyl C-C Dist. C17 -C22 1.37 Ang. PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) ..... 4 PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.557 27 PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF .... 2 PLAT041_ALERT_1_C Calc. and Reported SumFormula Strings Differ ? PLAT042_ALERT_1_C Calc. and Reported MoietyFormula Strings Differ ?
Alert level G FORMU01_ALERT_2_G There is a discrepancy between the atom counts in the _chemical_formula_sum and the formula from the _atom_site* data. Atom count from _chemical_formula_sum:C47 H45 Cl2 Cu2 N4 O4.5 Atom count from the _atom_site data: C94 H90 Cl4 Cu4 N8 O9 CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected. CELLZ01_ALERT_1_G ALERT: Large difference may be due to a symmetry error - see SYMMG tests From the CIF: _cell_formula_units_Z 2 From the CIF: _chemical_formula_sum C47 H45 Cl2 Cu2 N4 O4.5 TEST: Compare cell contents of formula and atom_site data atom Z*formula cif sites diff C 94.00 188.00 -94.00 H 90.00 180.00 -90.00 Cl 4.00 8.00 -4.00 Cu 4.00 8.00 -4.00 N 8.00 16.00 -8.00 O 9.00 18.00 -9.00 PLAT301_ALERT_3_G Note: Main Residue Disorder ................... 3.00 Perc. PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 13 PLAT128_ALERT_4_G Alternate Setting of Space-group P21/c ....... P21/n PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature 293 K PLAT302_ALERT_4_G Note: Anion/Solvent Disorder ................... 42.00 Perc. PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels .......... 6 PLAT764_ALERT_4_G Overcomplete CIF Bond List Detected (Rep/Expd) . 1.11 Ratio
5 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 12 ALERT level C = Check and explain 11 ALERT level G = General alerts; check 10 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 9 ALERT type 2 Indicator that the structure model may be wrong or deficient 7 ALERT type 3 Indicator that the structure quality may be low 4 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

Phenol-based Schiff base metal complexes with NNO donors have recently drawn more attention due to their adjustable coordination ability and interesting application in bio-inorganic and therapeutic chemistry (Generex & Barton, 2010; Fenton et al., 2010; Reisner et al., 2008). As part of our investigations on the phenol based Schiff base complexes (Gupta et al., 2002, 2007, 2008), we herein report the synthesis and crystal structure of a dimeric copper (II) complex. The molecular structure of the complex is shown in Fig.1. The dimeric complex consists of [Cu2Cl2{(µ-O)C6H2(Me-4)PhCN(CH 2)2NCPh}2].2H2O. 0.5 EtOH wherein the copper (II) ion is five- coordinated with four imine N, two bridging phenolato O and two Cl at axial positions, giving a square pyramidal geometry [τ = 0.185 and 0.199 for Cu1 and Cu2, respectively (Addison et al., 1984)]. The copper atoms are displaced from the basal planes by 0.430 (1) and 0.436 (1) Å, respectively. The average Cu—Cl, Cu—O and Cu—N bond lengths are 2.428 (2), 1.931 (13) and 1.927 (4) A, respectively. the non-bonding Cu···..Cu distances are 2.9556 (12) and 2.9506 (12) Å. The packing is stabilized through solvent mediated intermolecular hydrogen bonds.

Related literature top

For general background to phenol-based Schiff base metal complexes with N,N,O donors, see: Generex & Barton (2010); Fenton et al., (2010); Reisner et al. (2008). For related phenol-based Schiff base complexes, see: Gupta et al. (2002, 2007, 2008). For a description of the geometry of pentacoordinated atoms, see: Addison et al. (1984).

Experimental top

Copper (II) chloride dihydrate (0.086 g, 0.51 mmol) dissolved in dry ethanol (20 ml) was added dropwise to an ethanol solution of tridentate ligand, 2-{N-(2-aminoethyl)benzimidoyl}-6-benzoyl-4-methylphenol (aebmpH) (0.365 g, 1.02 mmol) and heated to reflux. The clear solution so obtained was allowed to cool and dark green crystals suitable for X-ray diffraction were obtained in 40° yield.

Refinement top

The diamine chain of one of the dimers in the asymmetric unit is disordered. The site occupancy of the disordered components were refined [0.680 (5)/0.320 (5)]. The H atom bound to C atoms were restrained as riding atoms with d(C—H) = 0.93Å for aromatic CH and 0.97Å for secondary CH2 groups and 0.96Å for CH3 groups with Uiso(H) = 1.2Uequ(C). The hydroxyl hydrogen of ethanol solvate was fixed at 0.82 Å. The crystals did not scatter beyond 2θ of 46.7°. Recrystallization and fresh data collection did not improve the situation.

Structure description top

Phenol-based Schiff base metal complexes with NNO donors have recently drawn more attention due to their adjustable coordination ability and interesting application in bio-inorganic and therapeutic chemistry (Generex & Barton, 2010; Fenton et al., 2010; Reisner et al., 2008). As part of our investigations on the phenol based Schiff base complexes (Gupta et al., 2002, 2007, 2008), we herein report the synthesis and crystal structure of a dimeric copper (II) complex. The molecular structure of the complex is shown in Fig.1. The dimeric complex consists of [Cu2Cl2{(µ-O)C6H2(Me-4)PhCN(CH 2)2NCPh}2].2H2O. 0.5 EtOH wherein the copper (II) ion is five- coordinated with four imine N, two bridging phenolato O and two Cl at axial positions, giving a square pyramidal geometry [τ = 0.185 and 0.199 for Cu1 and Cu2, respectively (Addison et al., 1984)]. The copper atoms are displaced from the basal planes by 0.430 (1) and 0.436 (1) Å, respectively. The average Cu—Cl, Cu—O and Cu—N bond lengths are 2.428 (2), 1.931 (13) and 1.927 (4) A, respectively. the non-bonding Cu···..Cu distances are 2.9556 (12) and 2.9506 (12) Å. The packing is stabilized through solvent mediated intermolecular hydrogen bonds.

For general background to phenol-based Schiff base metal complexes with N,N,O donors, see: Generex & Barton (2010); Fenton et al., (2010); Reisner et al. (2008). For related phenol-based Schiff base complexes, see: Gupta et al. (2002, 2007, 2008). For a description of the geometry of pentacoordinated atoms, see: Addison et al. (1984).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT-Plus (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoides are drawn at 50° probability level. Only one of the molecule in the asymmetric unit is shown for clarity. Solvent molecules are omitted.
[Figure 2] Fig. 2. The packing diagram of the molecules in the unit cell viewed down the a axis. The intermolecular H-bonding interactions are shown with dashed lines.
Dichlorido[µ-10,21-dimethyl-2,7,13,18-tetraphenyl-3,6,14,17- tetraazatricyclo[17.3.1.18,12]tetracosa-1(23),2,6,8,10,12(24),13,17,19,21- decaene-23,24-diolato]dicopper(II) ethanol hemisolvate dihydrate top
Crystal data top
[Cu2(C46H38N4O2)Cl2]·0.5C2H6O·2H2OF(000) = 1932
Mr = 935.85Dx = 1.340 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 6395 reflections
a = 15.1983 (4) Åθ = 2.1–22.5°
b = 16.2680 (5) ŵ = 1.08 mm1
c = 19.3344 (5) ÅT = 293 K
β = 103.964 (2)°Needle, brown
V = 4639.1 (2) Å30.30 × 0.20 × 0.20 mm
Z = 2
Data collection top
Bruker Kappa APEXII CCD
diffractometer
6669 independent reflections
Radiation source: fine-focus sealed tube4664 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.054
ω and φ scanθmax = 23.3°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Bruker, 1999)
h = 1616
Tmin = 0.738, Tmax = 0.813k = 1818
36333 measured reflectionsl = 2121
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.137H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.0717P)2 + 3.5141P]
where P = (Fo2 + 2Fc2)/3
6669 reflections(Δ/σ)max = 0.001
575 parametersΔρmax = 0.51 e Å3
13 restraintsΔρmin = 0.34 e Å3
Crystal data top
[Cu2(C46H38N4O2)Cl2]·0.5C2H6O·2H2OV = 4639.1 (2) Å3
Mr = 935.85Z = 2
Monoclinic, P21/nMo Kα radiation
a = 15.1983 (4) ŵ = 1.08 mm1
b = 16.2680 (5) ÅT = 293 K
c = 19.3344 (5) Å0.30 × 0.20 × 0.20 mm
β = 103.964 (2)°
Data collection top
Bruker Kappa APEXII CCD
diffractometer
6669 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 1999)
4664 reflections with I > 2σ(I)
Tmin = 0.738, Tmax = 0.813Rint = 0.054
36333 measured reflectionsθmax = 23.3°
Refinement top
R[F2 > 2σ(F2)] = 0.04413 restraints
wR(F2) = 0.137H atoms treated by a mixture of independent and constrained refinement
S = 1.05Δρmax = 0.51 e Å3
6669 reflectionsΔρmin = 0.34 e Å3
575 parameters
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*/UeqOcc. (<1)
Cu11.09084 (3)0.47211 (2)1.039422 (19)0.04010 (11)
Cu20.52512 (3)0.47246 (3)0.57491 (2)0.04566 (12)
Cl11.17520 (9)0.59912 (7)1.06780 (7)0.0984 (4)
Cl20.53483 (9)0.59915 (7)0.64348 (7)0.0943 (4)
O10.97493 (14)0.50362 (14)1.05664 (11)0.0473 (6)
O20.58164 (14)0.50367 (15)0.49873 (11)0.0519 (7)
O30.5295 (5)0.5394 (8)0.7957 (6)0.283 (7)0.50
H40.54850.53410.83890.425*0.50
O1W0.5206 (3)0.7508 (3)0.5223 (2)0.1308 (15)
H1W10.5577 (17)0.7868 (13)0.538 (2)0.196*
H1W20.526 (3)0.7165 (15)0.5540 (15)0.196*
O2W0.6367 (7)0.4809 (11)0.9357 (13)0.370 (13)0.50
H2W10.61630.44220.95690.555*0.50
H2W20.61630.46490.88610.555*0.50
O3W0.5749 (10)0.3569 (14)1.0049 (11)0.443 (12)0.50
H3W10.52020.36690.96090.665*0.50
H3W20.56440.36021.04420.665*0.50
N11.12269 (17)0.41850 (16)1.13139 (13)0.0396 (7)
N21.16146 (18)0.39153 (17)1.00425 (13)0.0458 (8)
N30.63697 (17)0.41998 (16)0.62346 (13)0.0435 (7)
N40.46031 (18)0.39075 (18)0.61374 (15)0.0554 (9)
C11.04385 (19)0.48096 (18)0.88252 (15)0.0341 (8)
C21.1145 (2)0.42521 (19)0.87872 (15)0.0369 (8)
C31.1337 (2)0.4126 (2)0.81264 (16)0.0443 (9)
H31.18050.37680.81010.053*
C41.0874 (2)0.4498 (2)0.75130 (16)0.0446 (9)
C51.0176 (2)0.50157 (19)0.75585 (16)0.0392 (8)
H50.98470.52650.71430.047*
C60.99364 (19)0.51866 (18)0.81944 (15)0.0350 (8)
C70.9157 (2)0.57477 (18)0.81663 (15)0.0362 (8)
C80.8847 (2)0.62559 (19)0.75101 (15)0.0400 (9)
C90.9455 (3)0.6785 (2)0.73011 (16)0.0494 (10)
H91.00640.67830.75430.059*
C100.9154 (3)0.7317 (2)0.67306 (19)0.0651 (12)
H100.95570.76800.65990.078*
C110.8266 (3)0.7308 (2)0.63641 (19)0.0720 (13)
H110.80680.76670.59840.086*
C120.7674 (3)0.6784 (3)0.65477 (19)0.0695 (13)
H120.70730.67780.62880.083*
C130.7953 (2)0.6251 (2)0.71241 (17)0.0513 (10)
H130.75400.58930.72480.062*
C141.2011 (2)0.3657 (2)1.13193 (18)0.0608 (11)
H14A1.25630.39721.14860.073*
H14B1.20200.32071.16500.073*
C151.1991 (3)0.3324 (3)1.06185 (18)0.0741 (13)
H15A1.16270.28281.05460.089*
H15B1.26020.31771.05960.089*
C161.1640 (2)0.3759 (2)0.93993 (16)0.0393 (8)
C171.2154 (2)0.3023 (2)0.92484 (16)0.0430 (9)
C181.1723 (3)0.2301 (2)0.90520 (18)0.0561 (10)
H181.10950.22740.89700.067*
C191.2206 (3)0.1607 (3)0.8974 (2)0.0750 (13)
H191.19050.11120.88470.090*
C201.3116 (3)0.1643 (3)0.9080 (2)0.0838 (14)
H201.34410.11720.90290.101*
C211.3553 (3)0.2362 (3)0.9260 (2)0.0807 (14)
H211.41790.23870.93230.097*
C221.3082 (2)0.3061 (3)0.93507 (19)0.0614 (11)
H221.33880.35540.94800.074*
C231.1097 (3)0.4335 (3)0.68094 (18)0.0719 (12)
H23A1.12620.37690.67850.108*
H23B1.15930.46790.67640.108*
H23C1.05760.44550.64300.108*
C240.6667 (2)0.52384 (19)0.50571 (15)0.0368 (8)
C250.3096 (2)0.41742 (19)0.54154 (15)0.0372 (8)
C260.2183 (2)0.39777 (19)0.53150 (16)0.0412 (9)
H260.20230.35920.56180.049*
C270.1505 (2)0.4319 (2)0.47948 (16)0.0396 (8)
C280.1757 (2)0.48855 (19)0.43462 (16)0.0387 (8)
H280.13050.51250.39920.046*
C290.7350 (2)0.48847 (18)0.56032 (15)0.0356 (8)
C300.7164 (2)0.42868 (19)0.61303 (15)0.0382 (8)
C310.7943 (2)0.37859 (19)0.65308 (17)0.0424 (9)
C320.8411 (2)0.3293 (2)0.61612 (19)0.0515 (10)
H320.82680.33070.56660.062*
C330.9089 (3)0.2780 (2)0.6522 (2)0.0712 (13)
H330.93890.24390.62680.085*
C340.9321 (3)0.2768 (3)0.7248 (3)0.0818 (15)
H340.97810.24220.74890.098*
C350.8880 (3)0.3265 (3)0.7621 (2)0.0721 (13)
H350.90440.32600.81170.087*
C360.8191 (2)0.3776 (2)0.72694 (18)0.0533 (10)
H360.78930.41130.75280.064*
C370.6168 (3)0.3678 (4)0.6819 (3)0.0512 (14)0.680 (5)
H37A0.61410.40170.72260.061*0.680 (5)
H37B0.66380.32690.69700.061*0.680 (5)
C380.5260 (3)0.3264 (4)0.6524 (3)0.0598 (17)0.680 (5)
H38A0.53250.28280.61980.072*0.680 (5)
H38B0.50370.30260.69090.072*0.680 (5)
C37'0.6112 (7)0.3476 (9)0.6580 (6)0.0512 (14)0.320 (5)
H37C0.65840.33470.70010.061*0.320 (5)
H37D0.60470.30110.62570.061*0.320 (5)
C38'0.5228 (7)0.3623 (8)0.6789 (7)0.0598 (17)0.320 (5)
H38C0.50100.31190.69580.072*0.320 (5)
H38D0.53030.40360.71610.072*0.320 (5)
C390.3754 (2)0.3723 (2)0.59562 (17)0.0444 (9)
C400.3429 (2)0.2996 (2)0.62927 (18)0.0482 (9)
C410.3327 (3)0.2247 (2)0.5969 (2)0.0681 (12)
H410.34410.21840.55200.082*
C420.3054 (3)0.1576 (3)0.6310 (3)0.0912 (17)
H420.30080.10590.60980.109*
C430.2855 (3)0.1676 (3)0.6957 (3)0.0975 (16)
H430.26520.12300.71760.117*
C440.2948 (3)0.2402 (3)0.7275 (2)0.0872 (15)
H440.28200.24580.77190.105*
C450.3234 (2)0.3077 (3)0.6954 (2)0.0652 (12)
H450.32960.35850.71810.078*
C460.0538 (2)0.4050 (2)0.46937 (19)0.0549 (10)
H46A0.03820.40440.51460.082*
H46B0.04650.35090.44900.082*
H46C0.01470.44260.43800.082*
C470.3985 (7)0.4819 (7)0.8194 (8)0.250 (11)0.50
H47A0.33470.47440.79970.375*0.50
H47B0.40880.49740.86860.375*0.50
H47C0.42980.43140.81570.375*0.50
C480.4334 (9)0.5483 (9)0.7789 (9)0.292 (9)0.50
H48A0.40840.54200.72800.350*0.50
H48B0.41670.60210.79320.350*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0408 (2)0.0455 (2)0.03363 (19)0.01844 (18)0.00837 (16)0.00292 (17)
Cu20.0359 (2)0.0530 (2)0.0464 (2)0.00232 (19)0.00656 (18)0.02143 (19)
Cl10.1143 (9)0.0656 (7)0.1098 (9)0.0300 (7)0.0164 (8)0.0062 (7)
Cl20.1024 (9)0.0662 (7)0.1126 (9)0.0039 (7)0.0227 (8)0.0161 (7)
O10.0457 (12)0.0634 (14)0.0318 (11)0.0272 (11)0.0076 (10)0.0027 (10)
O20.0329 (12)0.0715 (15)0.0484 (13)0.0072 (11)0.0040 (10)0.0273 (12)
O30.356 (14)0.345 (15)0.188 (9)0.215 (12)0.141 (10)0.125 (9)
O1W0.115 (3)0.156 (3)0.126 (3)0.016 (3)0.037 (2)0.023 (3)
O2W0.065 (6)0.325 (19)0.71 (4)0.021 (9)0.071 (12)0.06 (2)
O3W0.179 (12)0.61 (3)0.51 (2)0.054 (16)0.029 (14)0.38 (2)
N10.0407 (14)0.0414 (15)0.0360 (13)0.0166 (12)0.0075 (12)0.0054 (12)
N20.0478 (15)0.0525 (16)0.0367 (14)0.0245 (13)0.0094 (12)0.0040 (12)
N30.0389 (14)0.0464 (15)0.0441 (14)0.0024 (13)0.0079 (12)0.0175 (13)
N40.0385 (15)0.0663 (19)0.0591 (17)0.0008 (14)0.0074 (13)0.0333 (15)
C10.0316 (15)0.0389 (17)0.0325 (15)0.0062 (14)0.0090 (13)0.0023 (14)
C20.0344 (16)0.0396 (17)0.0377 (16)0.0095 (14)0.0106 (13)0.0003 (14)
C30.0442 (17)0.0458 (19)0.0465 (18)0.0181 (16)0.0179 (15)0.0028 (15)
C40.0471 (18)0.052 (2)0.0375 (17)0.0124 (16)0.0164 (15)0.0008 (15)
C50.0440 (18)0.0428 (18)0.0294 (15)0.0084 (15)0.0065 (14)0.0006 (14)
C60.0312 (16)0.0340 (17)0.0392 (16)0.0051 (14)0.0072 (13)0.0050 (14)
C70.0375 (16)0.0336 (16)0.0331 (16)0.0081 (14)0.0000 (14)0.0052 (14)
C80.0495 (19)0.0389 (17)0.0285 (15)0.0117 (16)0.0032 (14)0.0051 (14)
C90.066 (2)0.0419 (19)0.0377 (17)0.0053 (18)0.0082 (16)0.0042 (15)
C100.105 (3)0.046 (2)0.049 (2)0.007 (2)0.026 (2)0.0054 (17)
C110.105 (3)0.062 (2)0.041 (2)0.033 (2)0.003 (2)0.0060 (19)
C120.077 (3)0.075 (3)0.045 (2)0.034 (2)0.009 (2)0.003 (2)
C130.050 (2)0.054 (2)0.0442 (19)0.0151 (18)0.0004 (16)0.0048 (17)
C140.061 (2)0.072 (2)0.054 (2)0.0405 (19)0.0219 (17)0.0171 (18)
C150.094 (3)0.085 (3)0.045 (2)0.059 (2)0.0195 (19)0.0149 (19)
C160.0315 (16)0.0468 (18)0.0407 (17)0.0097 (15)0.0112 (14)0.0001 (15)
C170.0429 (18)0.051 (2)0.0375 (16)0.0212 (16)0.0149 (14)0.0071 (15)
C180.061 (2)0.051 (2)0.062 (2)0.0161 (19)0.0267 (18)0.0044 (18)
C190.105 (3)0.054 (2)0.071 (2)0.023 (2)0.031 (2)0.005 (2)
C200.115 (3)0.077 (3)0.066 (2)0.061 (3)0.032 (2)0.010 (2)
C210.063 (2)0.112 (3)0.072 (3)0.053 (2)0.025 (2)0.008 (2)
C220.050 (2)0.076 (3)0.061 (2)0.023 (2)0.0181 (18)0.001 (2)
C230.084 (3)0.094 (3)0.0438 (19)0.040 (2)0.0275 (19)0.006 (2)
C240.0306 (16)0.0436 (18)0.0364 (16)0.0036 (15)0.0082 (13)0.0047 (14)
C250.0341 (16)0.0409 (17)0.0376 (16)0.0016 (15)0.0106 (13)0.0034 (14)
C260.0467 (18)0.0422 (18)0.0395 (16)0.0061 (15)0.0196 (14)0.0023 (14)
C270.0346 (16)0.0431 (18)0.0406 (17)0.0060 (15)0.0080 (14)0.0016 (15)
C280.0357 (17)0.0415 (18)0.0360 (16)0.0005 (15)0.0027 (14)0.0007 (14)
C290.0374 (17)0.0324 (16)0.0368 (16)0.0027 (14)0.0085 (14)0.0005 (13)
C300.0400 (17)0.0355 (17)0.0359 (16)0.0073 (15)0.0029 (14)0.0010 (14)
C310.0374 (18)0.0356 (17)0.0480 (19)0.0053 (15)0.0019 (15)0.0076 (15)
C320.049 (2)0.0409 (19)0.060 (2)0.0059 (17)0.0038 (17)0.0013 (17)
C330.052 (2)0.051 (2)0.105 (3)0.008 (2)0.007 (2)0.002 (2)
C340.058 (2)0.067 (3)0.102 (3)0.009 (2)0.015 (2)0.029 (3)
C350.066 (3)0.077 (3)0.058 (2)0.015 (2)0.014 (2)0.024 (2)
C360.051 (2)0.054 (2)0.048 (2)0.0067 (18)0.0026 (17)0.0053 (17)
C370.046 (2)0.067 (3)0.040 (3)0.006 (2)0.008 (2)0.024 (2)
C380.042 (2)0.061 (4)0.076 (4)0.008 (3)0.014 (2)0.035 (3)
C37'0.046 (2)0.067 (3)0.040 (3)0.006 (2)0.008 (2)0.024 (2)
C38'0.042 (2)0.061 (4)0.076 (4)0.008 (3)0.014 (2)0.035 (3)
C390.0420 (18)0.0497 (19)0.0457 (18)0.0010 (16)0.0190 (15)0.0100 (15)
C400.0364 (17)0.054 (2)0.057 (2)0.0025 (16)0.0180 (15)0.0226 (17)
C410.066 (2)0.058 (2)0.085 (3)0.003 (2)0.028 (2)0.012 (2)
C420.071 (3)0.055 (3)0.149 (4)0.005 (2)0.029 (3)0.020 (3)
C430.075 (3)0.086 (3)0.140 (4)0.004 (3)0.044 (3)0.064 (3)
C440.080 (3)0.108 (4)0.085 (3)0.010 (3)0.042 (2)0.048 (3)
C450.060 (2)0.074 (3)0.067 (2)0.010 (2)0.0260 (19)0.025 (2)
C460.0427 (19)0.066 (2)0.057 (2)0.0076 (18)0.0131 (17)0.0036 (18)
C470.201 (18)0.156 (13)0.35 (3)0.001 (13)0.019 (18)0.134 (15)
C480.346 (18)0.231 (17)0.39 (2)0.177 (15)0.275 (16)0.174 (15)
Geometric parameters (Å, º) top
Cu1—N21.920 (3)C18—H180.9300
Cu1—O1i1.9258 (19)C19—C201.349 (6)
Cu1—N11.934 (2)C19—H190.9300
Cu1—O11.939 (2)C20—C211.350 (6)
Cu1—Cl12.4238 (12)C20—H200.9300
Cu1—Cu1i2.9563 (7)C21—C221.377 (6)
Cu2—N41.913 (3)C21—H210.9300
Cu2—O2ii1.922 (2)C22—H220.9300
Cu2—N31.931 (2)C23—H23A0.9600
Cu2—O21.943 (2)C23—H23B0.9600
Cu2—Cl22.4356 (13)C23—H23C0.9600
Cu2—Cu2ii2.9512 (8)C24—C291.412 (4)
O1—C1i1.300 (4)C24—C25ii1.427 (4)
O1—Cu1i1.9258 (19)C25—C261.391 (4)
O2—C241.309 (4)C25—C24ii1.427 (4)
O2—Cu2ii1.922 (2)C25—C391.458 (4)
O3—C481.425 (13)C26—C271.372 (4)
O3—H40.8200C26—H260.9300
O1W—H1W10.820 (17)C27—C281.382 (4)
O1W—H1W20.818 (17)C27—C461.500 (4)
O2W—H2W10.8494C28—C29ii1.388 (4)
O2W—H2W20.9688C28—H280.9300
O3W—H3W11.0487C29—C28ii1.388 (4)
O3W—H3W20.8157C29—C301.485 (4)
N1—C7i1.282 (4)C30—C311.491 (4)
N1—C141.467 (4)C31—C321.380 (5)
N2—C161.279 (4)C31—C361.386 (5)
N2—C151.478 (4)C32—C331.378 (5)
N3—C301.279 (4)C32—H320.9300
N3—C37'1.453 (13)C33—C341.363 (6)
N3—C371.502 (6)C33—H330.9300
N4—C391.289 (4)C34—C351.363 (6)
N4—C38'1.458 (12)C34—H340.9300
N4—C381.514 (6)C35—C361.380 (5)
C1—O1i1.300 (4)C35—H350.9300
C1—C61.413 (4)C36—H360.9300
C1—C21.421 (4)C37—C381.517 (7)
C2—C31.393 (4)C37—H37A0.9700
C2—C161.476 (4)C37—H37B0.9700
C3—C41.366 (4)C38—H38A0.9700
C3—H30.9300C38—H38B0.9700
C4—C51.374 (5)C37'—C38'1.512 (13)
C4—C231.502 (5)C37'—H37C0.9700
C5—C61.392 (4)C37'—H37D0.9700
C5—H50.9300C38'—H38C0.9700
C6—C71.486 (4)C38'—H38D0.9700
C7—N1i1.282 (4)C39—C401.490 (5)
C7—C81.492 (4)C40—C411.363 (5)
C8—C131.384 (4)C40—C451.386 (5)
C8—C91.392 (5)C41—C421.389 (6)
C9—C101.390 (5)C41—H410.9300
C9—H90.9300C42—C431.366 (7)
C10—C111.363 (6)C42—H420.9300
C10—H100.9300C43—C441.323 (7)
C11—C121.348 (6)C43—H430.9300
C11—H110.9300C44—C451.382 (6)
C12—C131.395 (5)C44—H440.9300
C12—H120.9300C45—H450.9300
C13—H130.9300C46—H46A0.9600
C14—C151.452 (5)C46—H46B0.9600
C14—H14A0.9700C46—H46C0.9600
C14—H14B0.9700C47—C481.505 (10)
C15—H15A0.9700C47—H47A0.9600
C15—H15B0.9700C47—H47B0.9600
C16—C171.496 (4)C47—H47C0.9600
C17—C181.354 (5)C48—H48A0.9700
C17—C221.378 (5)C48—H48B0.9700
C18—C191.374 (5)
N2—Cu1—O1i90.16 (10)C18—C19—H19119.9
N2—Cu1—N188.88 (11)C19—C20—C21119.9 (4)
O1i—Cu1—N1159.32 (11)C19—C20—H20120.0
N2—Cu1—O1148.23 (11)C21—C20—H20120.0
O1i—Cu1—O180.20 (10)C20—C21—C22120.7 (4)
N1—Cu1—O189.86 (10)C20—C21—H21119.7
N2—Cu1—Cl1110.60 (9)C22—C21—H21119.7
O1i—Cu1—Cl199.59 (8)C21—C22—C17119.4 (4)
N1—Cu1—Cl1100.07 (8)C21—C22—H22120.3
O1—Cu1—Cl1100.87 (8)C17—C22—H22120.3
N2—Cu1—Cu1i124.02 (7)C4—C23—H23A109.5
O1i—Cu1—Cu1i40.26 (7)C4—C23—H23B109.5
N1—Cu1—Cu1i127.43 (8)H23A—C23—H23B109.5
O1—Cu1—Cu1i39.93 (6)C4—C23—H23C109.5
Cl1—Cu1—Cu1i103.43 (4)H23A—C23—H23C109.5
N4—Cu2—O2ii90.49 (10)H23B—C23—H23C109.5
N4—Cu2—N388.75 (11)O2—C24—C29120.3 (3)
O2ii—Cu2—N3159.37 (11)O2—C24—C25ii119.8 (3)
N4—Cu2—O2147.45 (12)C29—C24—C25ii119.9 (3)
O2ii—Cu2—O280.47 (10)C26—C25—C24ii117.5 (3)
N3—Cu2—O289.18 (10)C26—C25—C39118.2 (3)
N4—Cu2—Cl2110.11 (10)C24ii—C25—C39124.2 (3)
O2ii—Cu2—Cl299.31 (8)C27—C26—C25123.9 (3)
N3—Cu2—Cl2100.31 (9)C27—C26—H26118.1
O2—Cu2—Cl2102.22 (8)C25—C26—H26118.1
N4—Cu2—Cu2ii124.09 (8)C26—C27—C28117.2 (3)
O2ii—Cu2—Cu2ii40.49 (7)C26—C27—C46121.1 (3)
N3—Cu2—Cu2ii126.88 (8)C28—C27—C46121.6 (3)
O2—Cu2—Cu2ii39.97 (6)C27—C28—C29ii123.4 (3)
Cl2—Cu2—Cu2ii104.16 (4)C27—C28—H28118.3
C1i—O1—Cu1i131.06 (19)C29ii—C28—H28118.3
C1i—O1—Cu1127.82 (18)C28ii—C29—C24118.2 (3)
Cu1i—O1—Cu199.80 (10)C28ii—C29—C30118.2 (3)
C24—O2—Cu2ii131.45 (19)C24—C29—C30123.6 (3)
C24—O2—Cu2126.42 (19)N3—C30—C29121.6 (3)
Cu2ii—O2—Cu299.54 (10)N3—C30—C31121.3 (3)
C48—O3—H4109.5C29—C30—C31117.1 (3)
H1W1—O1W—H1W2105 (3)C32—C31—C36118.7 (3)
H2W1—O2W—H2W2102.3C32—C31—C30119.5 (3)
H3W1—O3W—H3W2116.8C36—C31—C30121.7 (3)
C7i—N1—C14124.5 (3)C33—C32—C31120.4 (4)
C7i—N1—Cu1128.4 (2)C33—C32—H32119.8
C14—N1—Cu1107.0 (2)C31—C32—H32119.8
C16—N2—C15120.4 (3)C34—C33—C32120.4 (4)
C16—N2—Cu1129.1 (2)C34—C33—H33119.8
C15—N2—Cu1109.0 (2)C32—C33—H33119.8
C30—N3—C37'122.1 (5)C35—C34—C33119.9 (4)
C30—N3—C37123.6 (3)C35—C34—H34120.0
C30—N3—Cu2128.9 (2)C33—C34—H34120.0
C37'—N3—Cu2106.2 (4)C34—C35—C36120.5 (4)
C37—N3—Cu2107.4 (2)C34—C35—H35119.7
C39—N4—C38'124.2 (5)C36—C35—H35119.7
C39—N4—C38118.2 (3)C35—C36—C31120.0 (4)
C39—N4—Cu2129.2 (2)C35—C36—H36120.0
C38'—N4—Cu2105.7 (5)C31—C36—H36120.0
C38—N4—Cu2109.5 (3)N3—C37—C38107.5 (4)
O1i—C1—C6120.4 (3)N3—C37—H37A110.2
O1i—C1—C2120.2 (2)C38—C37—H37A110.2
C6—C1—C2119.3 (3)N3—C37—H37B110.2
C3—C2—C1118.0 (3)C38—C37—H37B110.2
C3—C2—C16118.4 (3)H37A—C37—H37B108.5
C1—C2—C16123.4 (3)N4—C38—C37108.1 (4)
C4—C3—C2123.6 (3)N4—C38—H38A110.1
C4—C3—H3118.2C37—C38—H38A110.1
C2—C3—H3118.2N4—C38—H38B110.1
C3—C4—C5117.4 (3)C37—C38—H38B110.1
C3—C4—C23121.8 (3)H38A—C38—H38B108.4
C5—C4—C23120.8 (3)N3—C37'—C38'110.5 (10)
C4—C5—C6123.4 (3)N3—C37'—H37C109.6
C4—C5—H5118.3C38'—C37'—H37C109.6
C6—C5—H5118.3N3—C37'—H37D109.6
C5—C6—C1118.3 (3)C38'—C37'—H37D109.6
C5—C6—C7117.8 (3)H37C—C37'—H37D108.1
C1—C6—C7123.9 (3)N4—C38'—C37'104.8 (9)
N1i—C7—C6122.2 (3)N4—C38'—H38C110.8
N1i—C7—C8120.6 (3)C37'—C38'—H38C110.8
C6—C7—C8117.1 (3)N4—C38'—H38D110.8
C13—C8—C9118.8 (3)C37'—C38'—H38D110.8
C13—C8—C7121.5 (3)H38C—C38'—H38D108.9
C9—C8—C7119.6 (3)N4—C39—C25123.1 (3)
C10—C9—C8120.0 (3)N4—C39—C40118.8 (3)
C10—C9—H9120.0C25—C39—C40118.1 (3)
C8—C9—H9120.0C41—C40—C45118.9 (3)
C11—C10—C9120.1 (4)C41—C40—C39121.5 (3)
C11—C10—H10120.0C45—C40—C39119.6 (3)
C9—C10—H10120.0C40—C41—C42119.9 (4)
C12—C11—C10120.6 (4)C40—C41—H41120.0
C12—C11—H11119.7C42—C41—H41120.0
C10—C11—H11119.7C43—C42—C41119.8 (5)
C11—C12—C13120.7 (4)C43—C42—H42120.1
C11—C12—H12119.7C41—C42—H42120.1
C13—C12—H12119.7C44—C43—C42120.7 (4)
C8—C13—C12119.8 (4)C44—C43—H43119.6
C8—C13—H13120.1C42—C43—H43119.6
C12—C13—H13120.1C43—C44—C45120.7 (5)
C15—C14—N1112.2 (3)C43—C44—H44119.7
C15—C14—H14A109.2C45—C44—H44119.7
N1—C14—H14A109.2C44—C45—C40119.9 (4)
C15—C14—H14B109.2C44—C45—H45120.0
N1—C14—H14B109.2C40—C45—H45120.0
H14A—C14—H14B107.9C27—C46—H46A109.5
C14—C15—N2112.2 (3)C27—C46—H46B109.5
C14—C15—H15A109.2H46A—C46—H46B109.5
N2—C15—H15A109.2C27—C46—H46C109.5
C14—C15—H15B109.2H46A—C46—H46C109.5
N2—C15—H15B109.2H46B—C46—H46C109.5
H15A—C15—H15B107.9C48—C47—H47A109.5
N2—C16—C2122.8 (3)C48—C47—H47B109.5
N2—C16—C17119.2 (3)H47A—C47—H47B109.5
C2—C16—C17117.9 (3)C48—C47—H47C109.5
C18—C17—C22119.2 (3)H47A—C47—H47C109.5
C18—C17—C16120.6 (3)H47B—C47—H47C109.5
C22—C17—C16120.0 (3)O3—C48—C47106.2 (9)
C17—C18—C19120.5 (4)O3—C48—H48A110.5
C17—C18—H18119.7C47—C48—H48A110.5
C19—C18—H18119.7O3—C48—H48B110.5
C20—C19—C18120.3 (4)C47—C48—H48B110.5
C20—C19—H19119.9H48A—C48—H48B108.7
N2—Cu1—O1—C1i117.9 (3)C11—C12—C13—C80.3 (6)
O1i—Cu1—O1—C1i168.0 (3)C7i—N1—C14—C15146.7 (3)
N1—Cu1—O1—C1i30.2 (3)Cu1—N1—C14—C1532.8 (4)
Cl1—Cu1—O1—C1i70.0 (3)N1—C14—C15—N235.9 (5)
Cu1i—Cu1—O1—C1i168.0 (3)C16—N2—C15—C14172.2 (3)
N2—Cu1—O1—Cu1i74.1 (2)Cu1—N2—C15—C1420.5 (4)
O1i—Cu1—O1—Cu1i0.0C15—N2—C16—C2169.5 (3)
N1—Cu1—O1—Cu1i161.78 (11)Cu1—N2—C16—C25.0 (5)
Cl1—Cu1—O1—Cu1i97.99 (9)C15—N2—C16—C177.4 (5)
N4—Cu2—O2—C24121.0 (3)Cu1—N2—C16—C17171.8 (2)
O2ii—Cu2—O2—C24163.3 (3)C3—C2—C16—N2169.0 (3)
N3—Cu2—O2—C2434.6 (3)C1—C2—C16—N215.4 (5)
Cl2—Cu2—O2—C2465.8 (3)C3—C2—C16—C1714.1 (4)
Cu2ii—Cu2—O2—C24163.3 (3)C1—C2—C16—C17161.5 (3)
N4—Cu2—O2—Cu2ii75.7 (2)N2—C16—C17—C1895.3 (4)
O2ii—Cu2—O2—Cu2ii0.0C2—C16—C17—C1881.7 (4)
N3—Cu2—O2—Cu2ii162.08 (12)N2—C16—C17—C2280.7 (4)
Cl2—Cu2—O2—Cu2ii97.55 (9)C2—C16—C17—C22102.3 (4)
N2—Cu1—N1—C7i162.5 (3)C22—C17—C18—C191.7 (5)
O1i—Cu1—N1—C7i75.0 (4)C16—C17—C18—C19174.4 (3)
O1—Cu1—N1—C7i14.2 (3)C17—C18—C19—C201.2 (6)
Cl1—Cu1—N1—C7i86.8 (3)C18—C19—C20—C210.4 (6)
Cu1i—Cu1—N1—C7i28.9 (3)C19—C20—C21—C221.3 (7)
N2—Cu1—N1—C1417.0 (2)C20—C21—C22—C170.7 (6)
O1i—Cu1—N1—C14104.5 (3)C18—C17—C22—C210.8 (5)
O1—Cu1—N1—C14165.2 (2)C16—C17—C22—C21175.3 (3)
Cl1—Cu1—N1—C1493.8 (2)Cu2ii—O2—C24—C29170.8 (2)
Cu1i—Cu1—N1—C14150.57 (19)Cu2—O2—C24—C2931.4 (4)
O1i—Cu1—N2—C168.0 (3)Cu2ii—O2—C24—C25ii10.0 (5)
N1—Cu1—N2—C16167.4 (3)Cu2—O2—C24—C25ii147.8 (2)
O1—Cu1—N2—C1679.5 (4)C24ii—C25—C26—C270.5 (5)
Cl1—Cu1—N2—C1692.3 (3)C39—C25—C26—C27175.7 (3)
Cu1i—Cu1—N2—C1631.3 (3)C25—C26—C27—C280.5 (5)
O1i—Cu1—N2—C15157.8 (2)C25—C26—C27—C46177.1 (3)
N1—Cu1—N2—C151.5 (2)C26—C27—C28—C29ii0.3 (5)
O1—Cu1—N2—C1586.4 (3)C46—C27—C28—C29ii176.2 (3)
Cl1—Cu1—N2—C15101.9 (2)O2—C24—C29—C28ii179.7 (3)
Cu1i—Cu1—N2—C15134.6 (2)C25ii—C24—C29—C28ii1.1 (5)
N4—Cu2—N3—C30164.0 (3)O2—C24—C29—C300.9 (5)
O2ii—Cu2—N3—C3075.9 (4)C25ii—C24—C29—C30178.3 (3)
O2—Cu2—N3—C3016.4 (3)C37'—N3—C30—C29161.7 (6)
Cl2—Cu2—N3—C3085.8 (3)C37—N3—C30—C29172.6 (3)
Cu2ii—Cu2—N3—C3030.8 (3)Cu2—N3—C30—C293.5 (4)
N4—Cu2—N3—C37'3.1 (6)C37'—N3—C30—C3117.9 (7)
O2ii—Cu2—N3—C37'85.0 (6)C37—N3—C30—C317.9 (5)
O2—Cu2—N3—C37'144.4 (6)Cu2—N3—C30—C31176.1 (2)
Cl2—Cu2—N3—C37'113.3 (6)C28ii—C29—C30—N3162.3 (3)
Cu2ii—Cu2—N3—C37'130.1 (6)C24—C29—C30—N317.1 (5)
N4—Cu2—N3—C3719.5 (3)C28ii—C29—C30—C3118.1 (4)
O2ii—Cu2—N3—C37107.6 (4)C24—C29—C30—C31162.5 (3)
O2—Cu2—N3—C37167.0 (3)N3—C30—C31—C32121.2 (4)
Cl2—Cu2—N3—C3790.7 (3)C29—C30—C31—C3258.4 (4)
Cu2ii—Cu2—N3—C37152.7 (2)N3—C30—C31—C3656.2 (4)
O2ii—Cu2—N4—C396.0 (3)C29—C30—C31—C36124.2 (3)
N3—Cu2—N4—C39165.3 (3)C36—C31—C32—C332.3 (5)
O2—Cu2—N4—C3978.8 (4)C30—C31—C32—C33175.2 (3)
Cl2—Cu2—N4—C3994.1 (3)C31—C32—C33—C341.7 (6)
Cu2ii—Cu2—N4—C3930.1 (4)C32—C33—C34—C350.2 (6)
O2ii—Cu2—N4—C38'175.0 (6)C33—C34—C35—C360.7 (6)
N3—Cu2—N4—C38'25.6 (6)C34—C35—C36—C310.0 (6)
O2—Cu2—N4—C38'112.1 (6)C32—C31—C36—C351.5 (5)
Cl2—Cu2—N4—C38'74.9 (6)C30—C31—C36—C35176.0 (3)
Cu2ii—Cu2—N4—C38'160.9 (6)C30—N3—C37—C38142.6 (4)
O2ii—Cu2—N4—C38153.1 (3)C37'—N3—C37—C3849.3 (12)
N3—Cu2—N4—C386.2 (3)Cu2—N3—C37—C3840.7 (5)
O2—Cu2—N4—C3880.3 (3)C39—N4—C38—C37167.8 (4)
Cl2—Cu2—N4—C38106.8 (3)C38'—N4—C38—C3757.4 (10)
Cu2ii—Cu2—N4—C38129.0 (3)Cu2—N4—C38—C3730.5 (5)
O1i—C1—C2—C3178.2 (3)N3—C37—C38—N446.5 (6)
C6—C1—C2—C32.5 (4)C30—N3—C37'—C38'166.6 (7)
O1i—C1—C2—C166.2 (5)C37—N3—C37'—C38'65.7 (14)
C6—C1—C2—C16173.1 (3)Cu2—N3—C37'—C38'30.9 (10)
C1—C2—C3—C41.0 (5)C39—N4—C38'—C37'143.6 (8)
C16—C2—C3—C4174.8 (3)C38—N4—C38'—C37'55.2 (10)
C2—C3—C4—C50.9 (5)Cu2—N4—C38'—C37'46.7 (10)
C2—C3—C4—C23179.2 (3)N3—C37'—C38'—N452.5 (12)
C3—C4—C5—C61.3 (5)C38'—N4—C39—C25163.2 (7)
C23—C4—C5—C6179.7 (3)C38—N4—C39—C25161.6 (4)
C4—C5—C6—C10.2 (5)Cu2—N4—C39—C254.0 (5)
C4—C5—C6—C7179.0 (3)C38'—N4—C39—C4019.2 (8)
O1i—C1—C6—C5178.6 (3)C38—N4—C39—C4016.0 (5)
C2—C1—C6—C52.1 (4)Cu2—N4—C39—C40173.6 (2)
O1i—C1—C6—C72.3 (5)C26—C25—C39—N4173.4 (3)
C2—C1—C6—C7177.0 (3)C24ii—C25—C39—N411.7 (5)
C5—C6—C7—N1i165.9 (3)C26—C25—C39—C409.0 (5)
C1—C6—C7—N1i13.2 (5)C24ii—C25—C39—C40165.9 (3)
C5—C6—C7—C815.8 (4)N4—C39—C40—C4195.9 (4)
C1—C6—C7—C8165.1 (3)C25—C39—C40—C4181.8 (4)
N1i—C7—C8—C1355.5 (4)N4—C39—C40—C4583.3 (4)
C6—C7—C8—C13126.2 (3)C25—C39—C40—C4599.0 (4)
N1i—C7—C8—C9120.7 (3)C45—C40—C41—C421.5 (5)
C6—C7—C8—C957.6 (4)C39—C40—C41—C42177.6 (3)
C13—C8—C9—C102.4 (5)C40—C41—C42—C432.5 (6)
C7—C8—C9—C10173.9 (3)C41—C42—C43—C442.3 (7)
C8—C9—C10—C111.6 (5)C42—C43—C44—C451.2 (7)
C9—C10—C11—C120.2 (6)C43—C44—C45—C400.2 (6)
C10—C11—C12—C131.1 (6)C41—C40—C45—C440.4 (5)
C9—C8—C13—C121.5 (5)C39—C40—C45—C44178.8 (3)
C7—C8—C13—C12174.7 (3)
Symmetry codes: (i) x+2, y+1, z+2; (ii) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H4···O2W0.822.202.96 (2)154
O1W—H1W1···Cl1iii0.82 (2)2.54 (2)3.355 (4)171 (4)
O1W—H1W2···Cl20.82 (2)2.56 (2)3.374 (4)174 (3)
O2W—H2W1···O3W0.851.862.71 (3)179
O2W—H2W2···O30.972.272.96 (2)127
Symmetry code: (iii) x1/2, y+3/2, z1/2.

Experimental details

Crystal data
Chemical formula[Cu2(C46H38N4O2)Cl2]·0.5C2H6O·2H2O
Mr935.85
Crystal system, space groupMonoclinic, P21/n
Temperature (K)293
a, b, c (Å)15.1983 (4), 16.2680 (5), 19.3344 (5)
β (°) 103.964 (2)
V3)4639.1 (2)
Z2
Radiation typeMo Kα
µ (mm1)1.08
Crystal size (mm)0.30 × 0.20 × 0.20
Data collection
DiffractometerBruker Kappa APEXII CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 1999)
Tmin, Tmax0.738, 0.813
No. of measured, independent and
observed [I > 2σ(I)] reflections
36333, 6669, 4664
Rint0.054
θmax (°)23.3
(sin θ/λ)max1)0.557
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.137, 1.05
No. of reflections6669
No. of parameters575
No. of restraints13
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.51, 0.34

Computer programs: APEX2 (Bruker, 2004), APEX2 and SAINT-Plus (Bruker, 2004), SAINT and XPREP (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H4···O2W0.822.202.96 (2)154.3
O1W—H1W1···Cl1i0.820 (17)2.543 (16)3.355 (4)171 (4)
O1W—H1W2···Cl20.818 (17)2.559 (17)3.374 (4)174 (3)
O2W—H2W1···O3W0.851.862.71 (3)178.5
O2W—H2W2···O30.972.272.96 (2)127.3
Symmetry code: (i) x1/2, y+3/2, z1/2.
 

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