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Acta Cryst. (2007). E63, m2933-m2934    [ doi:10.1107/S1600536807056267 ]

{N,N'-Bis[3-(2-nitrophenyl)prop-2-enylidene]ethylenediamine-[kappa]2N,N'}chlorido(triphenylphosphine-[kappa]P)copper(I)

M. H. Habibi, M. Montazerozohori, A. Lalegani, R. Mokhtari, R. W. Harrington and W. Clegg

Abstract top

The title complex, [CuCl(C20H18N4O4)(C18H15P)], has two molecules in the asymmetric unit. The Cu atom is four-coordinate in a distorted tetrahedral geometry, bonded to two imine N atoms of the Schiff base, Cl and PPh3; the main distortion is the small bite angle of the chelating Schiff base ligand. One triphenylphospine ligand adopts an approximate propeller conformation, with dihedral angles of 69.36 (14), 77.02 (12) and 82.44 (15)° for pairs of benzene rings, the normals of which make angles of 37.8, 65.4 and 72.6° with the P-Cu bond; the arrangement in the other triphenylphosphine ligand is rather less symmetrical, with dihedral angles of 63.41 (15), 70.67 (12) and 78.11 (12)° and angles of 20.3, 78.6 and 83.2° between the ring plane normals and the P-Cu bond. There are intermolecular C-H...Cl and C-H...O interactions. The crystal was a non-merohedral twin, with approximately equal contributions of the two domains.

Comment top

Transition metal complexes containing Schiff base ligands have been of great interest for many years (Yamada, 1999). These complexes play an important role in coordination chemistry related to catalysis and enzymatic reactions, magnetism and molecular architectures (Goswami & Eichhorn, 1999; Rybak-Akimova et al., 1998). The study of the variety of products in self-assembly processes between labile metal ions and flexible multidentate ligands is an interesting topic in supramolecular chemistry. The balance between the formation of different structures is often subtle. Factors that affect the coordination topology include not only the highly influential factors of metal and ligand coordination preferences, but also solvent-based influences, which have been extensively studied for silver(I) complexes (Amirnasr et al., 2006; Liu et al., 2005; Amirnasr et al., 2005; Khalaji et al., 2007). Here we report the results of the reaction of CuCl with N,N'-bis(2-nitrocinnamaldehyde)ethylenediamine and triphenylphosphine, which forms a copper(I) Schiff base complex, the crystal structure of which we have determined. The title complex is stable in dichloromethane for at least 24 h, but is decomposed in methanol much faster. A methanol solution exposed to the air slowly turns violet and finally green within 2 h. The complex is stable in air in the solid state for 2–3 weeks.

The asymmetric unit (Fig. 1) contains two complex molecules with essentially identical geometry. The bond lengths and angles around the Cu atoms are in good agreement with those found in similar copper(I) complexes (Barron et al., 1988). While a tetrahedral geometry is common for a four-coordinate copper(I) centre, the coordination in this complex is distorted by the restricted bite angle of the chelating ligand. The bond lengths in the chains of the ligand are consistent with extended electron delocalization.

The four nitro groups in the two independent molecules are twisted somewhat out of the planes of the benzene rings, with absolute O—N—C—C torsion angles in the range 17.2 (6)–33.6 (6)°. Dihedral angles between pairs of phenyl groups in the triphenylphosphine ligand are 82.44 (15), 77.02 (12) and 69.36 (14)° in one molecule, and 63.41 (15), 78.11 (12) and 70.67 (12)° in the other. Inspection shows that these rings form approximately a propeller arrangement in one molecule (angles between their normals and the P—Cu bond are 37.8, 65.4 and 72.6°), but a much less symmetrical arrangement in the other (corresponding angles are 20.3, 78.6 and 83.2°).

Molecules are linked via C—H···Cl and C—H···O interactions.

Related literature top

For related literature, see: Yamada (1999); Goswami & Eichhorn (1999); Rybak-Akimova et al. (1998); Amirnasr et al. (2005, 2006); Liu et al. (2005); Khalaji et al. (2007); Barron et al. (1988).

Experimental top

To a solution of 99 mg (1 mmol) CuCl in 5 ml acetonitrile a solution of 261 mg (1 mmol) of PPh3 in 5 ml acetonitrile was added. The mixture was stirred for 5 min and then 378 mg (1 mmol) of N,N'-bis(2-nitrocinnamaldehyde)ethylenediamine in 5 ml acetonitrile was added and the solution stirred for an additional 60 min. The volume of the solvent was reduced under vacuum to about 5 ml. The diffusion of diethyl ether vapour into the concentrated solution gave needle-like red crystals suitable for X-ray studies. The crystals were collected and dried in vacuo.

Refinement top

All H atoms were placed in idealized positions and constrained to ride on their parent atoms, with C—H = 0.95–0.99 Å, and with Uiso(H) = 1.2Ueq(C).

The crystal was found to be a non-merohedral twin, with symmetry-inequivalent reflections overlapping in the diffraction pattern, making it impossible to merge all equivalent reflections before the refinement. The deposited structure factors are in the format generated by the undocumented LIST 7 instruction of SHELXTL, in which the contributions of the twin components are identified following refinement of the twin fraction; this was 0.5095:0.4905 (6). The twin law (obtained as part of the cell and orientation matrix refinement and given to 3 decimal places) is: 1.009 0.019 0.013 / −0.059 0.999 0.030 / −0.140 − 0.098 0.986.

Computing details top

Data collection: GEMINI and SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2005); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and local programs.

Figures top
[Figure 1] Fig. 1. The asymmetric unit, with atom labels and 40% probability displacement ellipsoids. H atoms have been omitted for clarity.
{N,N'-Bis[3-(2-nitrophenyl)prop-2-enylidene]ethylenediamine- κ2N,N'}chlorido(triphenylphosphine-κP)copper(I) top
Crystal data top
[CuCl(C20H18N4O4)(C18H15P)]Z = 4
Mr = 739.64F000 = 1528
Triclinic, P1Dx = 1.392 Mg m−3
a = 8.4684 (10) ÅMo Kα radiation
λ = 0.71073 Å
b = 16.5749 (19) ÅCell parameters from 6328 reflections
c = 26.321 (3) Åθ = 2.5–26.5º
α = 100.338 (3)ºµ = 0.79 mm−1
β = 90.767 (3)ºT = 150 (2) K
γ = 103.499 (3)ºRod, red
V = 3528.2 (7) Å30.34 × 0.10 × 0.10 mm
Data collection top
Bruker SMART 1K CCD
diffractometer		33770 independent reflections
Radiation source: sealed tube21591 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.047
T = 150(2) Kθmax = 28.4º
thin–slice ω scansθmin = 1.4º
Absorption correction: multi-scan
(TWINABS; Bruker, 2005)		h = −11→11
Tmin = 0.753, Tmax = 0.901k = −22→21
56982 measured reflectionsl = −34→35
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.051H-atom parameters constrained
wR(F2) = 0.132  w = 1/[σ2(Fo2) + (0.0326P)2 + 12.0057P]
where P = (Fo2 + 2Fc2)/3
S = 1.10(Δ/σ)max = 0.001
33770 reflectionsΔρmax = 0.59 e Å−3
884 parametersΔρmin = −0.53 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
[CuCl(C20H18N4O4)(C18H15P)]γ = 103.499 (3)º
Mr = 739.64V = 3528.2 (7) Å3
Triclinic, P1Z = 4
a = 8.4684 (10) ÅMo Kα
b = 16.5749 (19) ŵ = 0.79 mm−1
c = 26.321 (3) ÅT = 150 (2) K
α = 100.338 (3)º0.34 × 0.10 × 0.10 mm
β = 90.767 (3)º
Data collection top
Bruker SMART 1K CCD
diffractometer		33770 independent reflections
Absorption correction: multi-scan
(TWINABS; Bruker, 2005)		21591 reflections with I > 2σ(I)
Tmin = 0.753, Tmax = 0.901Rint = 0.047
56982 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.051H-atom parameters constrained
wR(F2) = 0.132  w = 1/[σ2(Fo2) + (0.0326P)2 + 12.0057P]
where P = (Fo2 + 2Fc2)/3
S = 1.10Δρmax = 0.59 e Å−3
33770 reflectionsΔρmin = −0.53 e Å−3
884 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cu10.83930 (6)0.34287 (3)0.286307 (18)0.02188 (11)
Cl10.75924 (14)0.43883 (7)0.35090 (4)0.0358 (3)
P10.64450 (12)0.24294 (6)0.24358 (4)0.0224 (2)
O11.0781 (5)0.3844 (3)−0.03731 (13)0.0585 (10)
O21.1042 (4)0.3616 (3)0.03932 (13)0.0568 (10)
O31.1143 (5)0.1011 (2)0.45215 (13)0.0517 (9)
O41.0924 (5)0.0893 (3)0.53202 (13)0.0673 (12)
N11.0290 (4)0.3818 (2)0.00601 (13)0.0339 (8)
N21.0061 (4)0.42440 (19)0.24764 (11)0.0191 (6)
N31.0506 (4)0.3350 (2)0.32407 (12)0.0235 (7)
N41.0422 (6)0.1050 (2)0.49193 (15)0.0448 (10)
C10.8713 (5)0.4016 (2)0.01746 (15)0.0256 (9)
C20.7680 (6)0.3977 (3)−0.02449 (16)0.0336 (10)
H20.80320.3880−0.05870.040*
C30.6144 (6)0.4082 (3)−0.01604 (18)0.0409 (12)
H30.54250.4063−0.04450.049*
C40.5639 (5)0.4213 (3)0.03352 (18)0.0411 (12)
H40.45530.42560.03910.049*
C50.6702 (5)0.4284 (3)0.07542 (17)0.0346 (10)
H50.63450.43960.10950.042*
C60.8286 (5)0.4194 (3)0.06863 (15)0.0266 (9)
C70.9412 (5)0.4376 (2)0.11454 (14)0.0229 (8)
H71.05040.46680.11130.028*
C80.9034 (5)0.4169 (2)0.16037 (14)0.0226 (8)
H80.79850.38370.16480.027*
C91.0244 (4)0.4455 (2)0.20336 (14)0.0203 (8)
H91.12430.48260.19820.024*
C101.1457 (5)0.4580 (2)0.28535 (14)0.0226 (8)
H10A1.11640.49600.31530.027*
H10B1.23830.49070.26930.027*
C111.1923 (5)0.3841 (2)0.30284 (16)0.0254 (9)
H11A1.22820.34820.27320.030*
H11B1.28320.40490.32960.030*
C121.0730 (5)0.3071 (2)0.36506 (15)0.0240 (8)
H121.18060.31860.37990.029*
C130.9426 (5)0.2589 (2)0.38981 (15)0.0253 (9)
H130.83380.24960.37650.030*
C140.9718 (5)0.2269 (2)0.43105 (15)0.0280 (9)
H141.08240.23550.44250.034*
C150.8494 (5)0.1802 (3)0.46016 (15)0.0307 (10)
C160.6903 (6)0.1909 (3)0.46014 (18)0.0402 (11)
H160.66060.22650.43900.048*
C170.5754 (7)0.1512 (3)0.4900 (2)0.0514 (14)
H170.46800.15930.48890.062*
C180.6156 (8)0.0994 (3)0.5217 (2)0.0566 (16)
H180.53700.07350.54290.068*
C190.7692 (7)0.0860 (3)0.52203 (19)0.0513 (14)
H190.79750.05000.54310.062*
C200.8817 (6)0.1251 (3)0.49173 (16)0.0364 (11)
C210.5196 (4)0.2838 (2)0.20235 (16)0.0251 (9)
C220.5105 (4)0.3673 (2)0.21791 (15)0.0229 (8)
H220.57000.40040.24840.028*
C230.4149 (4)0.4027 (2)0.18919 (15)0.0249 (8)
H230.40960.45970.20010.030*
C240.3283 (5)0.3553 (3)0.14503 (17)0.0372 (11)
H240.26240.37940.12560.045*
C250.3372 (6)0.2727 (3)0.1291 (2)0.0568 (16)
H250.27690.23990.09860.068*
C260.4333 (6)0.2373 (3)0.1570 (2)0.0500 (14)
H260.44050.18070.14520.060*
C270.4928 (5)0.1833 (2)0.28019 (17)0.0306 (10)
C280.3288 (6)0.1827 (3)0.2772 (2)0.0466 (13)
H280.28980.21270.25420.056*
C290.2206 (7)0.1381 (3)0.3078 (3)0.068 (2)
H290.10860.13830.30560.082*
C300.2747 (8)0.0944 (3)0.3407 (2)0.0664 (19)
H300.20030.06410.36130.080*
C310.4375 (8)0.0938 (3)0.3442 (2)0.0561 (16)
H310.47520.06320.36710.067*
C320.5456 (6)0.1383 (3)0.31390 (17)0.0394 (11)
H320.65750.13790.31630.047*
C330.7079 (5)0.1586 (2)0.20031 (15)0.0250 (9)
C340.6046 (6)0.0798 (3)0.18249 (18)0.0379 (11)
H340.49590.06860.19300.045*
C350.6569 (7)0.0172 (3)0.14974 (17)0.0438 (12)
H350.5847−0.03650.13800.053*
C360.8133 (7)0.0332 (3)0.13436 (18)0.0480 (14)
H360.8496−0.00920.11160.058*
C370.9172 (6)0.1104 (4)0.1519 (2)0.0571 (16)
H371.02580.12100.14140.068*
C380.8655 (5)0.1734 (3)0.18492 (17)0.0373 (11)
H380.93880.22670.19690.045*
Cu20.48633 (6)0.68749 (3)0.219149 (18)0.02083 (11)
Cl20.33758 (12)0.58831 (6)0.15118 (4)0.0274 (2)
P20.38212 (12)0.79103 (6)0.25379 (4)0.0202 (2)
O50.9162 (6)0.9170 (3)−0.04751 (15)0.0868 (16)
O60.9493 (5)0.8923 (2)0.02872 (15)0.0607 (10)
O70.7323 (4)0.6617 (3)0.47157 (14)0.0558 (10)
O80.6781 (5)0.5964 (2)0.53537 (13)0.0609 (11)
N50.8623 (6)0.8960 (3)−0.00768 (16)0.0504 (12)
N60.7106 (4)0.7103 (2)0.18252 (12)0.0226 (7)
N70.6010 (4)0.61720 (19)0.25880 (11)0.0192 (6)
N80.6364 (5)0.6220 (3)0.49759 (14)0.0396 (9)
C390.6849 (6)0.8767 (3)−0.00442 (16)0.0394 (11)
C400.5976 (9)0.9098 (3)−0.0364 (2)0.0591 (16)
H400.65210.9428−0.05990.071*
C410.4332 (9)0.8953 (4)−0.0344 (2)0.0669 (19)
H410.37270.9179−0.05650.080*
C420.3541 (7)0.8476 (4)−0.0002 (2)0.0568 (15)
H420.23940.83810.00160.068*
C430.4423 (6)0.8134 (3)0.03156 (18)0.0402 (11)
H430.38650.77990.05450.048*
C440.6106 (6)0.8273 (3)0.03047 (15)0.0309 (10)
C450.6958 (5)0.7858 (3)0.06340 (16)0.0295 (9)
H450.79080.76990.05070.035*
C460.6514 (5)0.7686 (2)0.10935 (15)0.0258 (9)
H460.55690.78340.12330.031*
C470.7452 (5)0.7276 (2)0.13830 (15)0.0251 (9)
H470.83830.71280.12330.030*
C480.8224 (5)0.6720 (3)0.20750 (16)0.0270 (9)
H48A0.88130.71240.23790.032*
H48B0.90330.65700.18300.032*
C490.7239 (4)0.5931 (2)0.22429 (14)0.0226 (8)
H49A0.67020.55130.19370.027*
H49B0.79620.56720.24260.027*
C500.6007 (4)0.5961 (2)0.30332 (14)0.0204 (8)
H500.67530.56400.31010.024*
C510.4960 (4)0.6171 (2)0.34397 (14)0.0210 (8)
H510.41760.64790.33870.025*
C520.5109 (5)0.5926 (2)0.38895 (14)0.0231 (8)
H520.59810.56670.39290.028*
C530.4080 (5)0.6011 (2)0.43307 (15)0.0251 (9)
C540.2416 (5)0.5938 (3)0.42456 (17)0.0339 (10)
H540.19930.59130.39060.041*
C550.1368 (6)0.5901 (3)0.4644 (2)0.0442 (12)
H550.02480.58700.45770.053*
C560.1947 (7)0.5908 (3)0.51386 (18)0.0448 (13)
H560.12160.58520.54080.054*
C570.3585 (6)0.5997 (3)0.52404 (17)0.0396 (11)
H570.39970.60130.55810.047*
C580.4614 (5)0.6063 (3)0.48434 (15)0.0300 (9)
C590.5387 (5)0.8755 (2)0.29209 (16)0.0260 (9)
C600.5591 (5)0.8865 (3)0.34516 (17)0.0399 (11)
H600.48320.85300.36380.048*
C610.6920 (6)0.9472 (4)0.3714 (2)0.0571 (16)
H610.70360.95590.40810.068*
C620.8057 (6)0.9941 (4)0.3450 (2)0.0579 (16)
H620.89591.03490.36320.069*
C630.7883 (6)0.9819 (3)0.2919 (2)0.0516 (14)
H630.86681.01410.27330.062*
C640.6567 (5)0.9226 (3)0.26561 (19)0.0374 (11)
H640.64650.91390.22890.045*
C650.2164 (5)0.7695 (2)0.29703 (15)0.0237 (8)
C660.1528 (5)0.8326 (3)0.32549 (18)0.0387 (11)
H660.19850.89010.32370.046*
C670.0240 (6)0.8127 (3)0.35622 (19)0.0474 (13)
H67−0.01990.85610.37500.057*
C68−0.0414 (5)0.7288 (3)0.35961 (18)0.0414 (12)
H68−0.12720.71500.38180.050*
C690.0179 (5)0.6664 (3)0.33113 (18)0.0345 (10)
H69−0.02890.60910.33290.041*
C700.1455 (5)0.6858 (3)0.29972 (16)0.0273 (9)
H700.18510.64160.27990.033*
C710.2946 (4)0.8436 (2)0.20901 (15)0.0229 (8)
C720.2333 (5)0.7960 (3)0.16073 (15)0.0264 (9)
H720.24400.73950.15140.032*
C730.1567 (5)0.8307 (3)0.12622 (17)0.0355 (10)
H730.11570.79790.09330.043*
C740.1396 (5)0.9125 (3)0.1395 (2)0.0428 (12)
H740.08750.93620.11570.051*
C750.1982 (6)0.9595 (3)0.1873 (2)0.0437 (12)
H750.18531.01560.19650.052*
C760.2759 (5)0.9262 (3)0.22211 (18)0.0335 (10)
H760.31650.95950.25500.040*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0202 (2)0.0233 (2)0.0237 (2)0.00567 (19)0.00173 (19)0.0080 (2)
Cl10.0520 (7)0.0422 (6)0.0244 (5)0.0289 (5)0.0130 (5)0.0118 (5)
P10.0201 (5)0.0194 (5)0.0292 (5)0.0062 (4)0.0052 (4)0.0065 (4)
O10.071 (3)0.086 (3)0.0298 (19)0.039 (2)0.0203 (18)0.0127 (19)
O20.047 (2)0.105 (3)0.0319 (19)0.044 (2)0.0029 (16)0.015 (2)
O30.074 (3)0.064 (2)0.0325 (19)0.032 (2)0.0181 (18)0.0263 (17)
O40.114 (4)0.079 (3)0.0304 (19)0.054 (3)0.006 (2)0.0242 (19)
N10.038 (2)0.040 (2)0.0225 (19)0.0122 (17)0.0043 (16)0.0006 (16)
N20.0204 (16)0.0194 (16)0.0179 (16)0.0042 (13)0.0009 (13)0.0051 (13)
N30.0242 (17)0.0225 (17)0.0256 (17)0.0077 (14)0.0021 (14)0.0062 (14)
N40.075 (3)0.037 (2)0.030 (2)0.021 (2)0.005 (2)0.0156 (18)
C10.029 (2)0.028 (2)0.0202 (19)0.0060 (17)−0.0012 (17)0.0063 (17)
C20.049 (3)0.032 (2)0.019 (2)0.008 (2)−0.0046 (19)0.0050 (18)
C30.042 (3)0.048 (3)0.032 (3)0.008 (2)−0.018 (2)0.009 (2)
C40.027 (2)0.055 (3)0.043 (3)0.009 (2)−0.007 (2)0.015 (2)
C50.026 (2)0.051 (3)0.029 (2)0.010 (2)0.0010 (18)0.011 (2)
C60.025 (2)0.032 (2)0.024 (2)0.0051 (17)0.0009 (17)0.0097 (17)
C70.0190 (19)0.030 (2)0.0208 (19)0.0049 (16)0.0016 (16)0.0073 (16)
C80.0194 (19)0.029 (2)0.0203 (19)0.0056 (16)0.0045 (16)0.0085 (16)
C90.0202 (19)0.0208 (19)0.0207 (19)0.0047 (15)0.0036 (15)0.0061 (15)
C100.023 (2)0.023 (2)0.0200 (19)0.0009 (16)−0.0012 (16)0.0051 (16)
C110.020 (2)0.032 (2)0.027 (2)0.0070 (17)0.0005 (16)0.0129 (18)
C120.028 (2)0.023 (2)0.022 (2)0.0068 (16)−0.0039 (16)0.0066 (16)
C130.028 (2)0.026 (2)0.023 (2)0.0060 (17)0.0007 (17)0.0066 (17)
C140.034 (2)0.024 (2)0.025 (2)0.0043 (18)−0.0008 (18)0.0061 (17)
C150.042 (3)0.025 (2)0.021 (2)0.0008 (19)0.0024 (19)0.0033 (17)
C160.044 (3)0.035 (3)0.037 (3)0.001 (2)0.005 (2)0.005 (2)
C170.045 (3)0.053 (3)0.045 (3)−0.005 (3)0.012 (2)−0.001 (3)
C180.073 (4)0.047 (3)0.036 (3)−0.012 (3)0.025 (3)0.004 (2)
C190.081 (4)0.039 (3)0.031 (3)0.004 (3)0.020 (3)0.014 (2)
C200.059 (3)0.028 (2)0.020 (2)0.006 (2)0.005 (2)0.0061 (18)
C210.0173 (19)0.025 (2)0.033 (2)0.0060 (16)0.0014 (17)0.0047 (17)
C220.0156 (18)0.025 (2)0.027 (2)0.0010 (15)0.0039 (16)0.0069 (17)
C230.020 (2)0.025 (2)0.032 (2)0.0073 (16)0.0054 (17)0.0097 (17)
C240.029 (2)0.051 (3)0.035 (2)0.021 (2)−0.003 (2)0.004 (2)
C250.057 (3)0.058 (3)0.051 (3)0.029 (3)−0.031 (3)−0.020 (3)
C260.053 (3)0.037 (3)0.056 (3)0.022 (2)−0.024 (3)−0.014 (2)
C270.033 (2)0.0165 (19)0.039 (2)0.0021 (17)0.015 (2)0.0012 (18)
C280.034 (3)0.025 (2)0.082 (4)0.007 (2)0.026 (3)0.010 (2)
C290.047 (3)0.032 (3)0.123 (6)0.008 (2)0.054 (4)0.005 (3)
C300.080 (5)0.033 (3)0.072 (4)−0.006 (3)0.057 (4)−0.003 (3)
C310.083 (4)0.036 (3)0.036 (3)−0.012 (3)0.013 (3)0.004 (2)
C320.049 (3)0.032 (2)0.029 (2)−0.006 (2)0.008 (2)0.0038 (19)
C330.029 (2)0.026 (2)0.026 (2)0.0138 (17)0.0073 (17)0.0112 (17)
C340.049 (3)0.024 (2)0.042 (3)0.009 (2)0.020 (2)0.008 (2)
C350.078 (4)0.030 (2)0.031 (2)0.024 (3)0.012 (2)0.009 (2)
C360.070 (4)0.058 (3)0.028 (2)0.047 (3)0.000 (2)−0.003 (2)
C370.036 (3)0.092 (5)0.046 (3)0.035 (3)0.008 (2)−0.006 (3)
C380.029 (2)0.050 (3)0.033 (2)0.014 (2)0.005 (2)0.003 (2)
Cu20.0235 (2)0.0225 (2)0.0186 (2)0.00857 (19)0.00131 (19)0.00512 (19)
Cl20.0316 (5)0.0251 (5)0.0226 (5)−0.0003 (4)−0.0066 (4)0.0066 (4)
P20.0199 (5)0.0207 (5)0.0203 (5)0.0054 (4)−0.0003 (4)0.0041 (4)
O50.111 (4)0.091 (3)0.037 (2)−0.025 (3)0.031 (2)0.019 (2)
O60.058 (2)0.069 (3)0.051 (2)−0.001 (2)0.018 (2)0.022 (2)
O70.038 (2)0.084 (3)0.039 (2)−0.0008 (19)−0.0085 (16)0.019 (2)
O80.084 (3)0.063 (2)0.039 (2)0.024 (2)−0.026 (2)0.0117 (18)
N50.076 (3)0.034 (2)0.032 (2)−0.008 (2)0.023 (2)0.0073 (19)
N60.0194 (16)0.0241 (17)0.0228 (17)0.0009 (13)0.0000 (13)0.0061 (14)
N70.0200 (16)0.0194 (16)0.0183 (16)0.0040 (13)0.0025 (13)0.0047 (13)
N80.050 (3)0.045 (2)0.0229 (19)0.014 (2)−0.0131 (18)0.0021 (17)
C390.069 (3)0.028 (2)0.020 (2)0.009 (2)0.008 (2)0.0053 (18)
C400.115 (6)0.038 (3)0.030 (3)0.027 (3)0.005 (3)0.013 (2)
C410.115 (6)0.064 (4)0.037 (3)0.051 (4)−0.012 (3)0.012 (3)
C420.069 (4)0.065 (4)0.047 (3)0.039 (3)−0.008 (3)0.008 (3)
C430.048 (3)0.043 (3)0.035 (3)0.018 (2)0.001 (2)0.012 (2)
C440.049 (3)0.027 (2)0.018 (2)0.011 (2)0.0038 (19)0.0059 (17)
C450.029 (2)0.029 (2)0.029 (2)0.0047 (18)0.0056 (18)0.0071 (18)
C460.026 (2)0.028 (2)0.023 (2)0.0042 (17)0.0033 (17)0.0074 (17)
C470.021 (2)0.029 (2)0.026 (2)0.0025 (16)0.0068 (17)0.0103 (17)
C480.018 (2)0.036 (2)0.029 (2)0.0054 (17)0.0016 (17)0.0140 (19)
C490.022 (2)0.028 (2)0.0200 (19)0.0099 (16)0.0035 (16)0.0064 (16)
C500.0179 (19)0.0212 (19)0.0218 (19)0.0024 (15)−0.0027 (15)0.0068 (15)
C510.0203 (19)0.026 (2)0.0167 (18)0.0048 (16)−0.0005 (15)0.0061 (15)
C520.0197 (19)0.028 (2)0.0204 (19)0.0027 (16)−0.0016 (15)0.0047 (16)
C530.031 (2)0.026 (2)0.0178 (19)0.0068 (17)0.0010 (17)0.0039 (16)
C540.033 (2)0.040 (3)0.028 (2)0.008 (2)0.0029 (19)0.0035 (19)
C550.034 (3)0.047 (3)0.050 (3)0.007 (2)0.015 (2)0.006 (2)
C560.063 (4)0.037 (3)0.033 (3)0.009 (2)0.028 (2)0.006 (2)
C570.062 (3)0.035 (3)0.021 (2)0.011 (2)0.010 (2)0.0061 (19)
C580.041 (3)0.028 (2)0.021 (2)0.0070 (19)0.0013 (18)0.0058 (17)
C590.020 (2)0.024 (2)0.033 (2)0.0088 (16)−0.0026 (17)0.0009 (17)
C600.027 (2)0.058 (3)0.031 (2)0.009 (2)−0.0029 (19)−0.002 (2)
C610.033 (3)0.083 (4)0.042 (3)0.013 (3)−0.012 (2)−0.021 (3)
C620.021 (2)0.066 (4)0.067 (4)0.002 (2)−0.006 (3)−0.027 (3)
C630.030 (3)0.048 (3)0.063 (4)−0.005 (2)0.002 (2)−0.007 (3)
C640.030 (2)0.034 (2)0.043 (3)−0.0004 (19)0.002 (2)0.003 (2)
C650.021 (2)0.028 (2)0.023 (2)0.0056 (16)−0.0009 (16)0.0049 (16)
C660.034 (3)0.034 (3)0.041 (3)0.003 (2)0.010 (2)−0.003 (2)
C670.040 (3)0.059 (3)0.037 (3)0.011 (2)0.012 (2)−0.006 (2)
C680.023 (2)0.066 (3)0.033 (3)0.003 (2)0.0040 (19)0.012 (2)
C690.021 (2)0.042 (3)0.044 (3)0.0036 (19)−0.0019 (19)0.025 (2)
C700.020 (2)0.031 (2)0.033 (2)0.0052 (17)−0.0043 (17)0.0125 (18)
C710.0150 (18)0.024 (2)0.032 (2)0.0053 (15)0.0015 (16)0.0096 (17)
C720.025 (2)0.029 (2)0.028 (2)0.0074 (17)0.0019 (17)0.0107 (18)
C730.026 (2)0.051 (3)0.033 (2)0.010 (2)−0.0045 (19)0.013 (2)
C740.030 (2)0.055 (3)0.056 (3)0.019 (2)0.002 (2)0.031 (3)
C750.041 (3)0.036 (3)0.064 (3)0.019 (2)0.002 (3)0.022 (2)
C760.029 (2)0.028 (2)0.045 (3)0.0078 (18)−0.003 (2)0.008 (2)
Geometric parameters (Å, °) top
Cu1—Cl12.3332 (11)Cu2—Cl22.3253 (11)
Cu1—P12.1762 (11)Cu2—P22.1730 (11)
Cu1—N22.121 (3)Cu2—N62.127 (3)
Cu1—N32.077 (3)Cu2—N72.080 (3)
P1—C211.823 (4)P2—C591.823 (4)
P1—C271.827 (4)P2—C651.829 (4)
P1—C331.826 (4)P2—C711.829 (4)
O1—N11.223 (4)O5—N51.224 (5)
O2—N11.216 (4)O6—N51.220 (5)
O3—N41.218 (5)O7—N81.220 (5)
O4—N41.224 (5)O8—N81.227 (5)
N1—C11.470 (5)N5—C391.468 (7)
N2—C91.277 (5)N6—C471.270 (5)
N2—C101.468 (5)N6—C481.465 (5)
N3—C111.462 (5)N7—C491.469 (5)
N3—C121.277 (5)N7—C501.282 (4)
N4—C201.473 (6)N8—C581.470 (6)
C1—C21.382 (5)C39—C401.377 (7)
C1—C61.397 (5)C39—C441.398 (6)
C2—H20.950C40—H400.950
C2—C31.368 (6)C40—C411.360 (9)
C3—H30.950C41—H410.950
C3—C41.374 (7)C41—C421.381 (8)
C4—H40.950C42—H420.950
C4—C51.385 (6)C42—C431.388 (6)
C5—H50.950C43—H430.950
C5—C61.394 (6)C43—C441.391 (6)
C6—C71.471 (5)C44—C451.475 (6)
C7—H70.950C45—H450.950
C7—C81.336 (5)C45—C461.331 (5)
C8—H80.950C46—H460.950
C8—C91.451 (5)C46—C471.447 (5)
C9—H90.950C47—H470.950
C10—H10A0.990C48—H48A0.990
C10—H10B0.990C48—H48B0.990
C10—C111.514 (5)C48—C491.520 (5)
C11—H11A0.990C49—H49A0.990
C11—H11B0.990C49—H49B0.990
C12—H120.950C50—H500.950
C12—C131.440 (5)C50—C511.445 (5)
C13—H130.950C51—H510.950
C13—C141.334 (5)C51—C521.332 (5)
C14—H140.950C52—H520.950
C14—C151.456 (6)C52—C531.467 (5)
C15—C161.400 (6)C53—C541.398 (6)
C15—C201.407 (6)C53—C581.399 (5)
C16—H160.950C54—H540.950
C16—C171.381 (7)C54—C551.383 (6)
C17—H170.950C55—H550.950
C17—C181.390 (8)C55—C561.382 (7)
C18—H180.950C56—H560.950
C18—C191.370 (8)C56—C571.378 (7)
C19—H190.950C57—H570.950
C19—C201.371 (6)C57—C581.373 (6)
C21—C221.391 (5)C59—C601.379 (6)
C21—C261.390 (6)C59—C641.395 (6)
C22—H220.950C60—H600.950
C22—C231.390 (5)C60—C611.398 (6)
C23—H230.950C61—H610.950
C23—C241.373 (6)C61—C621.371 (8)
C24—H240.950C62—H620.950
C24—C251.377 (7)C62—C631.376 (8)
C25—H250.950C63—H630.950
C25—C261.383 (6)C63—C641.382 (6)
C26—H260.950C64—H640.950
C27—C281.388 (6)C65—C661.392 (6)
C27—C321.388 (6)C65—C701.393 (5)
C28—H280.950C66—H660.950
C28—C291.396 (7)C66—C671.380 (6)
C29—H290.950C67—H670.950
C29—C301.362 (9)C67—C681.391 (7)
C30—H300.950C68—H680.950
C30—C311.383 (8)C68—C691.363 (6)
C31—H310.950C69—H690.950
C31—C321.391 (6)C69—C701.382 (6)
C32—H320.950C70—H700.950
C33—C341.388 (6)C71—C721.392 (5)
C33—C381.379 (6)C71—C761.397 (5)
C34—H340.950C72—H720.950
C34—C351.385 (6)C72—C731.386 (5)
C35—H350.950C73—H730.950
C35—C361.370 (7)C73—C741.381 (6)
C36—H360.950C74—H740.950
C36—C371.369 (8)C74—C751.373 (7)
C37—H370.950C75—H750.950
C37—C381.391 (7)C75—C761.383 (6)
C38—H380.950C76—H760.950
Cl1—Cu1—P1115.98 (5)Cl2—Cu2—P2117.85 (4)
Cl1—Cu1—N2101.81 (9)Cl2—Cu2—N696.77 (9)
Cl1—Cu1—N398.19 (9)Cl2—Cu2—N7104.00 (9)
P1—Cu1—N2121.16 (9)P2—Cu2—N6121.11 (9)
P1—Cu1—N3129.82 (9)P2—Cu2—N7126.11 (9)
N2—Cu1—N382.70 (12)N6—Cu2—N782.97 (12)
Cu1—P1—C21111.74 (13)Cu2—P2—C59110.15 (13)
Cu1—P1—C27118.29 (15)Cu2—P2—C65118.41 (13)
Cu1—P1—C33115.99 (14)Cu2—P2—C71116.39 (13)
C21—P1—C27102.3 (2)C59—P2—C65105.04 (18)
C21—P1—C33104.83 (18)C59—P2—C71104.04 (18)
C27—P1—C33101.88 (18)C65—P2—C71101.26 (17)
O1—N1—O2122.2 (4)O5—N5—O6122.8 (5)
O1—N1—C1118.6 (4)O5—N5—C39117.1 (5)
O2—N1—C1119.2 (3)O6—N5—C39120.1 (4)
Cu1—N2—C9140.3 (3)Cu2—N6—C47131.6 (3)
Cu1—N2—C10103.3 (2)Cu2—N6—C48108.0 (2)
C9—N2—C10116.1 (3)C47—N6—C48117.0 (3)
Cu1—N3—C11109.7 (2)Cu2—N7—C49104.9 (2)
Cu1—N3—C12131.3 (3)Cu2—N7—C50138.7 (3)
C11—N3—C12118.1 (3)C49—N7—C50116.2 (3)
O3—N4—O4123.6 (4)O7—N8—O8123.4 (4)
O3—N4—C20119.0 (4)O7—N8—C58118.6 (4)
O4—N4—C20117.4 (4)O8—N8—C58117.9 (4)
N1—C1—C2116.7 (4)N5—C39—C40117.3 (5)
N1—C1—C6120.2 (3)N5—C39—C44120.3 (4)
C2—C1—C6123.0 (4)C40—C39—C44122.4 (5)
C1—C2—H2120.5C39—C40—H40120.1
C1—C2—C3119.0 (4)C39—C40—C41119.8 (5)
H2—C2—C3120.5H40—C40—C41120.1
C2—C3—H3120.0C40—C41—H41120.0
C2—C3—C4120.1 (4)C40—C41—C42120.1 (5)
H3—C3—C4120.0H41—C41—C42120.0
C3—C4—H4119.8C41—C42—H42120.0
C3—C4—C5120.5 (4)C41—C42—C43119.9 (6)
H4—C4—C5119.8H42—C42—C43120.0
C4—C5—H5119.4C42—C43—H43119.3
C4—C5—C6121.3 (4)C42—C43—C44121.4 (5)
H5—C5—C6119.4H43—C43—C44119.3
C1—C6—C5116.0 (4)C39—C44—C43116.4 (4)
C1—C6—C7125.2 (4)C39—C44—C45124.9 (4)
C5—C6—C7118.5 (4)C43—C44—C45118.6 (4)
C6—C7—H7117.2C44—C45—H45117.1
C6—C7—C8125.7 (4)C44—C45—C46125.7 (4)
H7—C7—C8117.2H45—C45—C46117.1
C7—C8—H8120.4C45—C46—H46119.6
C7—C8—C9119.2 (4)C45—C46—C47120.8 (4)
H8—C8—C9120.4H46—C46—C47119.6
N2—C9—C8124.6 (4)N6—C47—C46124.0 (4)
N2—C9—H9117.7N6—C47—H47118.0
C8—C9—H9117.7C46—C47—H47118.0
N2—C10—H10A110.1N6—C48—H48A110.0
N2—C10—H10B110.1N6—C48—H48B110.0
N2—C10—C11108.0 (3)N6—C48—C49108.4 (3)
H10A—C10—H10B108.4H48A—C48—H48B108.4
H10A—C10—C11110.1H48A—C48—C49110.0
H10B—C10—C11110.1H48B—C48—C49110.0
N3—C11—C10108.6 (3)N7—C49—C48108.4 (3)
N3—C11—H11A110.0N7—C49—H49A110.0
N3—C11—H11B110.0N7—C49—H49B110.0
C10—C11—H11A110.0C48—C49—H49A110.0
C10—C11—H11B110.0C48—C49—H49B110.0
H11A—C11—H11B108.4H49A—C49—H49B108.4
N3—C12—H12118.5N7—C50—H50117.3
N3—C12—C13123.1 (4)N7—C50—C51125.3 (3)
H12—C12—C13118.5H50—C50—C51117.3
C12—C13—H13119.3C50—C51—H51120.4
C12—C13—C14121.3 (4)C50—C51—C52119.1 (4)
H13—C13—C14119.3H51—C51—C52120.4
C13—C14—H14117.0C51—C52—H52116.3
C13—C14—C15125.9 (4)C51—C52—C53127.4 (4)
H14—C14—C15117.0H52—C52—C53116.3
C14—C15—C16120.9 (4)C52—C53—C54119.9 (4)
C14—C15—C20123.8 (4)C52—C53—C58123.9 (4)
C16—C15—C20115.3 (4)C54—C53—C58115.7 (4)
C15—C16—H16119.2C53—C54—H54119.2
C15—C16—C17121.7 (5)C53—C54—C55121.7 (4)
H16—C16—C17119.2H54—C54—C55119.2
C16—C17—H17119.7C54—C55—H55119.9
C16—C17—C18120.5 (5)C54—C55—C56120.2 (5)
H17—C17—C18119.7H55—C55—C56119.9
C17—C18—H18120.2C55—C56—H56120.1
C17—C18—C19119.5 (5)C55—C56—C57119.9 (4)
H18—C18—C19120.2H56—C56—C57120.1
C18—C19—H19120.3C56—C57—H57120.5
C18—C19—C20119.4 (5)C56—C57—C58119.0 (4)
H19—C19—C20120.3H57—C57—C58120.5
N4—C20—C15119.6 (4)N8—C58—C53119.4 (4)
N4—C20—C19116.8 (4)N8—C58—C57117.2 (4)
C15—C20—C19123.6 (5)C53—C58—C57123.4 (4)
P1—C21—C22117.0 (3)P2—C59—C60123.0 (3)
P1—C21—C26124.5 (3)P2—C59—C64117.7 (3)
C22—C21—C26118.4 (4)C60—C59—C64118.6 (4)
C21—C22—H22119.7C59—C60—H60120.1
C21—C22—C23120.6 (4)C59—C60—C61119.8 (5)
H22—C22—C23119.7H60—C60—C61120.1
C22—C23—H23119.9C60—C61—H61119.5
C22—C23—C24120.2 (4)C60—C61—C62120.9 (5)
H23—C23—C24119.9H61—C61—C62119.5
C23—C24—H24120.1C61—C62—H62120.2
C23—C24—C25119.7 (4)C61—C62—C63119.6 (5)
H24—C24—C25120.1H62—C62—C63120.2
C24—C25—H25119.8C62—C63—H63120.0
C24—C25—C26120.5 (4)C62—C63—C64120.0 (5)
H25—C25—C26119.8H63—C63—C64120.0
C21—C26—C25120.5 (4)C59—C64—C63121.0 (5)
C21—C26—H26119.7C59—C64—H64119.5
C25—C26—H26119.7C63—C64—H64119.5
P1—C27—C28123.5 (4)P2—C65—C66123.1 (3)
P1—C27—C32118.1 (3)P2—C65—C70118.4 (3)
C28—C27—C32118.4 (4)C66—C65—C70118.4 (4)
C27—C28—H28119.8C65—C66—H66119.6
C27—C28—C29120.4 (5)C65—C66—C67120.7 (4)
H28—C28—C29119.8H66—C66—C67119.6
C28—C29—H29119.8C66—C67—H67120.1
C28—C29—C30120.4 (5)C66—C67—C68119.8 (5)
H29—C29—C30119.8H67—C67—C68120.1
C29—C30—H30119.8C67—C68—H68120.0
C29—C30—C31120.3 (5)C67—C68—C69119.9 (4)
H30—C30—C31119.8H68—C68—C69120.0
C30—C31—H31120.3C68—C69—H69119.7
C30—C31—C32119.4 (6)C68—C69—C70120.7 (4)
H31—C31—C32120.3H69—C69—C70119.7
C27—C32—C31121.1 (5)C65—C70—C69120.4 (4)
C27—C32—H32119.5C65—C70—H70119.8
C31—C32—H32119.5C69—C70—H70119.8
P1—C33—C34122.8 (3)P2—C71—C72117.5 (3)
P1—C33—C38118.7 (3)P2—C71—C76123.5 (3)
C34—C33—C38118.5 (4)C72—C71—C76118.8 (4)
C33—C34—H34119.4C71—C72—H72119.8
C33—C34—C35121.3 (5)C71—C72—C73120.3 (4)
H34—C34—C35119.4H72—C72—C73119.8
C34—C35—H35120.2C72—C73—H73119.8
C34—C35—C36119.6 (5)C72—C73—C74120.3 (4)
H35—C35—C36120.2H73—C73—C74119.8
C35—C36—H36120.1C73—C74—H74120.2
C35—C36—C37119.9 (4)C73—C74—C75119.7 (4)
H36—C36—C37120.1H74—C74—C75120.2
C36—C37—H37119.6C74—C75—H75119.6
C36—C37—C38120.8 (5)C74—C75—C76120.8 (4)
H37—C37—C38119.6H75—C75—C76119.6
C33—C38—C37120.0 (5)C71—C76—C75120.0 (4)
C33—C38—H38120.0C71—C76—H76120.0
C37—C38—H38120.0C75—C76—H76120.0
Cl1—Cu1—P1—C2169.27 (15)Cl2—Cu2—P2—C59−163.61 (15)
Cl1—Cu1—P1—C27−49.16 (16)Cl2—Cu2—P2—C6575.53 (15)
Cl1—Cu1—P1—C33−170.66 (14)Cl2—Cu2—P2—C71−45.55 (15)
N2—Cu1—P1—C21−54.84 (17)N6—Cu2—P2—C59−45.27 (18)
N2—Cu1—P1—C27−173.26 (18)N6—Cu2—P2—C65−166.13 (17)
N2—Cu1—P1—C3365.24 (17)N6—Cu2—P2—C7172.80 (17)
N3—Cu1—P1—C21−162.95 (18)N7—Cu2—P2—C5959.99 (18)
N3—Cu1—P1—C2778.6 (2)N7—Cu2—P2—C65−60.86 (18)
N3—Cu1—P1—C33−42.88 (19)N7—Cu2—P2—C71178.06 (17)
Cl1—Cu1—N2—C9−117.2 (4)Cl2—Cu2—N6—C4750.1 (4)
Cl1—Cu1—N2—C1070.1 (2)Cl2—Cu2—N6—C48−108.1 (2)
P1—Cu1—N2—C913.3 (4)P2—Cu2—N6—C47−78.3 (4)
P1—Cu1—N2—C10−159.42 (19)P2—Cu2—N6—C48123.5 (2)
N3—Cu1—N2—C9145.9 (4)N7—Cu2—N6—C47153.4 (4)
N3—Cu1—N2—C10−26.8 (2)N7—Cu2—N6—C48−4.8 (2)
Cl1—Cu1—N3—C11−103.5 (2)Cl2—Cu2—N7—C4970.3 (2)
Cl1—Cu1—N3—C1264.8 (4)Cl2—Cu2—N7—C50−115.7 (4)
P1—Cu1—N3—C11122.3 (2)P2—Cu2—N7—C49−148.61 (19)
P1—Cu1—N3—C12−69.4 (4)P2—Cu2—N7—C5025.4 (4)
N2—Cu1—N3—C11−2.6 (2)N6—Cu2—N7—C49−24.9 (2)
N2—Cu1—N3—C12165.7 (4)N6—Cu2—N7—C50149.1 (4)
O1—N1—C1—C218.3 (6)O5—N5—C39—C40−21.5 (6)
O1—N1—C1—C6−164.6 (4)O5—N5—C39—C44159.1 (4)
O2—N1—C1—C2−159.9 (4)O6—N5—C39—C40157.2 (5)
O2—N1—C1—C617.2 (6)O6—N5—C39—C44−22.1 (6)
N1—C1—C2—C3174.2 (4)N5—C39—C40—C41−178.8 (5)
C6—C1—C2—C3−2.8 (7)C44—C39—C40—C410.5 (8)
C1—C2—C3—C4−0.7 (7)C39—C40—C41—C420.1 (8)
C2—C3—C4—C53.3 (7)C40—C41—C42—C43−0.9 (9)
C3—C4—C5—C6−2.4 (7)C41—C42—C43—C441.0 (8)
C4—C5—C6—C1−1.0 (6)C42—C43—C44—C39−0.4 (7)
C4—C5—C6—C7172.8 (4)C42—C43—C44—C45−177.1 (4)
N1—C1—C6—C5−173.3 (4)N5—C39—C44—C43178.9 (4)
N1—C1—C6—C713.4 (6)N5—C39—C44—C45−4.6 (6)
C2—C1—C6—C53.6 (6)C40—C39—C44—C43−0.4 (7)
C2—C1—C6—C7−169.7 (4)C40—C39—C44—C45176.1 (4)
C1—C6—C7—C8−146.7 (4)C39—C44—C45—C46151.1 (4)
C5—C6—C7—C840.1 (6)C43—C44—C45—C46−32.5 (6)
C6—C7—C8—C9−174.8 (4)C44—C45—C46—C47−179.9 (4)
Cu1—N2—C9—C85.8 (6)Cu2—N6—C47—C4625.9 (6)
C10—N2—C9—C8177.9 (3)C48—N6—C47—C46−177.5 (4)
C7—C8—C9—N2−174.6 (4)C45—C46—C47—N6179.2 (4)
Cu1—N2—C10—C1151.4 (3)Cu2—N6—C48—C4933.0 (4)
C9—N2—C10—C11−123.4 (3)C47—N6—C48—C49−128.8 (4)
Cu1—N3—C11—C1031.3 (4)Cu2—N7—C49—C4850.5 (3)
C12—N3—C11—C10−138.7 (3)C50—N7—C49—C48−125.1 (3)
N2—C10—C11—N3−57.1 (4)N6—C48—C49—N7−57.3 (4)
Cu1—N3—C12—C1311.8 (6)Cu2—N7—C50—C513.2 (6)
C11—N3—C12—C13179.3 (3)C49—N7—C50—C51176.8 (3)
N3—C12—C13—C14176.4 (4)N7—C50—C51—C52−178.5 (4)
C12—C13—C14—C15177.6 (4)C50—C51—C52—C53−174.3 (4)
C13—C14—C15—C16−24.5 (6)C51—C52—C53—C5434.6 (6)
C13—C14—C15—C20158.6 (4)C51—C52—C53—C58−153.5 (4)
C14—C15—C16—C17−175.9 (4)C52—C53—C54—C55171.2 (4)
C20—C15—C16—C171.2 (6)C58—C53—C54—C55−1.4 (6)
C15—C16—C17—C180.7 (7)C53—C54—C55—C56−2.1 (7)
C16—C17—C18—C19−1.9 (8)C54—C55—C56—C573.4 (7)
C17—C18—C19—C201.1 (8)C55—C56—C57—C58−1.1 (7)
C18—C19—C20—N4−177.2 (4)C56—C57—C58—N8175.7 (4)
C18—C19—C20—C150.9 (7)C56—C57—C58—C53−2.7 (7)
C14—C15—C20—N4−6.9 (6)C52—C53—C58—N813.3 (6)
C14—C15—C20—C19175.0 (4)C52—C53—C58—C57−168.4 (4)
C16—C15—C20—N4176.0 (4)C54—C53—C58—N8−174.5 (4)
C16—C15—C20—C19−2.1 (6)C54—C53—C58—C573.8 (6)
O3—N4—C20—C15−33.6 (6)O7—N8—C58—C5328.6 (6)
O3—N4—C20—C19144.6 (5)O7—N8—C58—C57−149.8 (4)
O4—N4—C20—C15149.7 (4)O8—N8—C58—C53−153.6 (4)
O4—N4—C20—C19−32.1 (6)O8—N8—C58—C5728.0 (6)
Cu1—P1—C21—C22−27.4 (3)Cu2—P2—C59—C60−99.6 (4)
Cu1—P1—C21—C26152.9 (4)Cu2—P2—C59—C6470.7 (3)
C27—P1—C21—C22100.1 (3)C65—P2—C59—C6028.9 (4)
C27—P1—C21—C26−79.6 (4)C65—P2—C59—C64−160.8 (3)
C33—P1—C21—C22−153.9 (3)C71—P2—C59—C60134.9 (4)
C33—P1—C21—C2626.5 (5)C71—P2—C59—C64−54.8 (4)
P1—C21—C22—C23−178.6 (3)P2—C59—C60—C61173.4 (4)
C26—C21—C22—C231.1 (6)C64—C59—C60—C613.2 (7)
C21—C22—C23—C240.0 (6)C59—C60—C61—C62−2.2 (8)
C22—C23—C24—C25−0.5 (7)C60—C61—C62—C630.4 (8)
C23—C24—C25—C26−0.3 (8)C61—C62—C63—C640.1 (8)
C24—C25—C26—C211.5 (9)C62—C63—C64—C591.0 (8)
P1—C21—C26—C25177.8 (4)P2—C59—C64—C63−173.4 (4)
C22—C21—C26—C25−1.8 (8)C60—C59—C64—C63−2.7 (7)
Cu1—P1—C27—C28117.3 (4)Cu2—P2—C65—C66173.0 (3)
Cu1—P1—C27—C32−60.7 (4)Cu2—P2—C65—C70−10.2 (3)
C21—P1—C27—C28−5.9 (4)C59—P2—C65—C6649.5 (4)
C21—P1—C27—C32176.0 (3)C59—P2—C65—C70−133.6 (3)
C33—P1—C27—C28−114.2 (4)C71—P2—C65—C66−58.5 (4)
C33—P1—C27—C3267.8 (4)C71—P2—C65—C70118.3 (3)
P1—C27—C28—C29−177.6 (4)P2—C65—C66—C67177.8 (4)
C32—C27—C28—C290.4 (7)C70—C65—C66—C670.9 (7)
C27—C28—C29—C30−0.4 (8)C65—C66—C67—C681.2 (7)
C28—C29—C30—C310.1 (9)C66—C67—C68—C69−2.5 (7)
C29—C30—C31—C320.1 (8)C67—C68—C69—C701.6 (7)
P1—C27—C32—C31177.9 (4)C68—C69—C70—C650.5 (6)
C28—C27—C32—C31−0.3 (7)P2—C65—C70—C69−178.8 (3)
C30—C31—C32—C270.0 (7)C66—C65—C70—C69−1.8 (6)
Cu1—P1—C33—C34160.3 (3)Cu2—P2—C71—C7228.3 (3)
Cu1—P1—C33—C38−19.2 (4)Cu2—P2—C71—C76−156.5 (3)
C21—P1—C33—C34−75.9 (4)C59—P2—C71—C72149.6 (3)
C21—P1—C33—C38104.5 (3)C59—P2—C71—C76−35.2 (4)
C27—P1—C33—C3430.4 (4)C65—P2—C71—C72−101.6 (3)
C27—P1—C33—C38−149.1 (3)C65—P2—C71—C7673.6 (4)
P1—C33—C34—C35−179.9 (3)P2—C71—C72—C73176.1 (3)
C38—C33—C34—C35−0.4 (7)C76—C71—C72—C730.7 (6)
C33—C34—C35—C36−0.3 (7)C71—C72—C73—C74−0.4 (6)
C34—C35—C36—C370.7 (7)C72—C73—C74—C75−0.3 (7)
C35—C36—C37—C38−0.5 (8)C73—C74—C75—C760.7 (7)
P1—C33—C38—C37−179.9 (4)C74—C75—C76—C71−0.4 (7)
C34—C33—C38—C370.6 (7)P2—C71—C76—C75−175.5 (3)
C36—C37—C38—C33−0.1 (8)C72—C71—C76—C75−0.3 (6)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C7—H7···Cl2i0.952.823.683 (4)151
C9—H9···Cl2i0.952.693.585 (4)158
C12—H12···O8ii0.952.533.263 (5)134
C24—H24···O2iii0.952.563.377 (5)145
C30—H30···O3iii0.952.523.245 (6)133
C37—H37···O5iv0.952.523.114 (6)121
C50—H50···Cl10.952.733.595 (4)153
C67—H67···O4v0.952.593.372 (6)140
C72—H72···Cl20.952.803.716 (4)163
C74—H74···O6iii0.952.463.237 (6)139
Symmetry codes: (i) x+1, y, z; (ii) −x+2, −y+1, −z+1; (iii) x−1, y, z; (iv) −x+2, −y+1, −z; (v) −x+1, −y+1, −z+1.
Table 1
Selected geometric parameters (Å, °) top
Cu1—Cl12.3332 (11)Cu2—Cl22.3253 (11)
Cu1—P12.1762 (11)Cu2—P22.1730 (11)
Cu1—N22.121 (3)Cu2—N62.127 (3)
Cu1—N32.077 (3)Cu2—N72.080 (3)
Cl1—Cu1—P1115.98 (5)Cl2—Cu2—P2117.85 (4)
Cl1—Cu1—N2101.81 (9)Cl2—Cu2—N696.77 (9)
Cl1—Cu1—N398.19 (9)Cl2—Cu2—N7104.00 (9)
P1—Cu1—N2121.16 (9)P2—Cu2—N6121.11 (9)
P1—Cu1—N3129.82 (9)P2—Cu2—N7126.11 (9)
N2—Cu1—N382.70 (12)N6—Cu2—N782.97 (12)
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C7—H7···Cl2i0.952.823.683 (4)151
C9—H9···Cl2i0.952.693.585 (4)158
C12—H12···O8ii0.952.533.263 (5)134
C24—H24···O2iii0.952.563.377 (5)145
C30—H30···O3iii0.952.523.245 (6)133
C37—H37···O5iv0.952.523.114 (6)121
C50—H50···Cl10.952.733.595 (4)153
C67—H67···O4v0.952.593.372 (6)140
C72—H72···Cl20.952.803.716 (4)163
C74—H74···O6iii0.952.463.237 (6)139
Symmetry codes: (i) x+1, y, z; (ii) −x+2, −y+1, −z+1; (iii) x−1, y, z; (iv) −x+2, −y+1, −z; (v) −x+1, −y+1, −z+1.
Acknowledgements top

We thank the EPSRC (UK) and Isfahan University Centre of Excellence (Catalysis and Fuel cells) for financial support.

references
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