Tetra-μ3-iodo-tetra­kis[(cyclo­hexyl­diphenyl­phosphine-κP)copper(I)]

Seddigi, Z.S.; Hossain, G.M.G.; Banu, A.

doi:10.1107/S1600536807006204

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 63| Part 3| March 2007| Pages m756-m758

https://doi.org/10.1107/S1600536807006204

Tetra-μ₃-iodo-tetrakis[(cyclohexyldiphenylphosphine-κP)copper(I)]

Zaki S. Seddigi,^a G. M. Golzar Hossain ^b ^* and Afroza Banu ^c

^aDepartment of Chemistry, King Fahd University of Petroleum and Minerals, PO Box 5048, Dhahran 31261, Saudi Arabia, ^bDepartment of Chemistry, University of Dhaka, Dhaka 1000, Bangladesh, and ^cSchool of Chemistry, Cardiff University, Cardiff CF10 3AT, Wales
^*Correspondence e-mail: acsbd@yahoo.com

(Received 24 January 2007; accepted 5 February 2007; online 14 February 2007)

The molecule of the title compound, [Cu₄I₄(C₁₈H₂₁P)₄], which lies on a crystallographic twofold rotation axis, displays a cubane-like Cu₄I₄ core.

Comment

Phosphine complexes of copper(I) halides [(CuXL_n)_m] (X = halogen and L = phosphine), which display a wide range of coordination geometries, are useful as catalysts, as precursors to organocopper reagents (Taylor, 1994 ) and as starting materials for the preparation of heterometallic complexes (Albano et al., 1995 ; Kudinov et al., 1993 ). It was proposed that the title complex, (I), has an irregular cubane structure (Churchill & Kalra, 1974a ,b ,c ; Churchill & Rotella, 1977 ), which is confirmed in the present study. The tetranuclear molecule lies on a crystallographic twofold rotation axis (Fig. 1).

The Cu₄I₄ core is a slightly irregular cubane with alternating copper(I) and iodide ions. The Cu atom exists in a tetrahedral environment, being linked to three I atoms and to the P atom of the cyclohexyldiphenylphosphine ligand.

The copper–iodine bond lengths show a significant range of values. The average of the bond lengths is in good agreement with the values of 2.6837 (13) and 2.6767 (15) Å in the Cu₄I₄ cores of other regular cubane-like adducts (Churchill & Kalra, 1974a,b,c; Churchill & Rotella, 1977). The six copper–copper contact distances are similar to reported values. The iodine–iodine contacts are also comparable to reported values, as are the copper–phosphorus bond distances.

There are van der Waals repulsive forces that may be responsible for the distortion of the six faces of the cubane core; the distortion manifests itself in the small Cu—I—Cu angles and in the non-planarity of the four-membered rings defining the faces of the cube.

Figure 1
The central coren of (I)

, showing the atom-labeling scheme. Displacement ellipsoids are drawn at the 50% probability level. The symmetry code is given in Table 1

Figure 2
The molecular structure of complex (I)

. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented by circles of arbitrary size.

Experimental

Cyclohexyldiphenylphosphine (0.235 g, 1 mmol) and copper(I) iodide (0.135 g, 2 mmol) were dissolved in 30 ml of acetone. After refluxing the mixture for one day, the hot solution was filtered. Cuboidal crystals were obtained upon recrystallization from the same solvent.

Crystal data

[Cu₄I₄(C₁₈H₂₁P)₄]
M_r = 1835.03
Monoclinic, C 2/c
a = 22.7712 (3) Å
b = 15.6704 (3) Å
c = 21.9311 (5) Å
β = 116.054 (1)°
V = 7030.5 (2) Å³
Z = 4
D_x = 1.734 Mg m⁻³
Mo Kα radiation
μ = 3.08 mm⁻¹
T = 150 (2) K
Cuboid, colorless
0.26 × 0.22 × 0.20 mm

Data collection

Nonius KappaCCD diffractometer
ω scans
Absorption correction: multi-scan (SORTAV; Blessing, 1995 ) T_min = 0.501, T_max = 0.578 (expected range = 0.469–0.540)
63740 measured reflections
8032 independent reflections
6289 reflections with I > 2σ(I)
R_int = 0.127
θ_max = 27.5°

Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.061
wR(F²) = 0.125
S = 1.21
8032 reflections
331 parameters
H-atom parameters constrained
w = 1/[σ²(F_o²) + 97.862P] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max = 0.001
Δρ_max = 1.00 e Å⁻³
Δρ_min = −0.92 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

I1—Cu1	2.6976 (11)
I1—Cu1ⁱ	2.6849 (10)
I1—Cu2	2.6645 (10)
I2—Cu2	2.6543 (11)
I2—Cu1	2.7077 (10)
I2—Cu2ⁱ	2.7667 (11)
Cu1—Cu2	2.8631 (13)
Cu1—Cu2ⁱ	3.0292 (13)
Cu2—Cu2ⁱ	3.0570 (18)

Cu1ⁱ—I1—Cu1	70.07 (4)
Cu2—I1—Cu1ⁱ	68.98 (3)
Cu2—I1—Cu1	64.54 (3)
Cu2—I2—Cu1	64.54 (3)
Cu2—I2—Cu2ⁱ	68.62 (3)
Cu1—I2—Cu2ⁱ	67.18 (3)
I1ⁱ—Cu1—I1	103.98 (3)
I1ⁱ—Cu1—I2	107.90 (3)
I1—Cu1—I2	112.27 (4)
I1ⁱ—Cu1—Cu2	107.34 (4)
I1—Cu1—Cu2	57.17 (3)
I2—Cu1—Cu2	56.83 (3)
I1ⁱ—Cu1—Cu2ⁱ	55.19 (3)
I1—Cu1—Cu2ⁱ	102.49 (4)
I2—Cu1—Cu2ⁱ	57.34 (3)
Cu2—Cu1—Cu2ⁱ	62.43 (4)
I2—Cu2—I1	115.10 (4)
I2—Cu2—I2ⁱ	104.49 (3)
I1—Cu2—I2ⁱ	106.78 (4)
I2—Cu2—Cu1	58.64 (3)
I1—Cu2—Cu1	58.29 (3)
I2ⁱ—Cu2—Cu1	107.27 (4)
I2—Cu2—Cu1ⁱ	105.64 (4)
I1—Cu2—Cu1ⁱ	55.83 (3)
I2ⁱ—Cu2—Cu1ⁱ	55.48 (3)
Cu1—Cu2—Cu1ⁱ	63.18 (4)
I2—Cu2—Cu2ⁱ	57.43 (3)
I1—Cu2—Cu2ⁱ	102.56 (2)
I2ⁱ—Cu2—Cu2ⁱ	53.95 (3)
Cu1—Cu2—Cu2ⁱ	61.45 (3)
Cu1ⁱ—Cu2—Cu2ⁱ	56.12 (3)
Symmetry code: (i) $[-x+1, y, -z+{\script{3\over 2}}]$ .

The data did not diffract well and the mosaicity was high so the R_int value was high. H atoms were placed in calculated positions (C—H = 0.95–1.00 Å) and included as riding atoms, with U_iso(H) values of 1.2U_eq of the attached C atoms. The final difference Fourier map had a large peak/hole 1.00 Å from atom C14..

Data collection: COLLECT (Nonius, 2000 ); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ); data reduction: SCALEPACK and DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536807006204/ng2211sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807006204/ng2211Isup2.hkl

Computing details top

Data collection: COLLECT (Nonius, 2000); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK and DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Tetra-µ₃-iodo-tetrakis[(cyclohexyldiphenylphosphine-κP)copper(I)] top

Crystal data top

[Cu₄I₄(C₁₈H₂₁P)₄]	F(000) = 3616
M_r = 1835.03	D_x = 1.734 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 8077 reflections
a = 22.7712 (3) Å	θ = 2.9–27.5°
b = 15.6704 (3) Å	µ = 3.08 mm⁻¹
c = 21.9311 (5) Å	T = 150 K
β = 116.054 (1)°	Cuboid, colorless
V = 7030.5 (2) Å³	0.26 × 0.22 × 0.20 mm
Z = 4

Data collection top

Nonius KappaCCD diffractometer	8032 independent reflections
Radiation source: fine-focus sealed tube	6289 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.127
ω scans	θ_max = 27.5°, θ_min = 3.0°
Absorption correction: multi-scan	h = −29→29
T_min = 0.501, T_max = 0.578	k = −20→19
63740 measured reflections	l = −28→28

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.125	H-atom parameters constrained
S = 1.21	w = 1/[σ²(F_o²) + 97.862P] where P = (F_o² + 2F_c²)/3
8032 reflections	(Δ/σ)_max = 0.001
331 parameters	Δρ_max = 1.01 e Å⁻³
24 restraints	Δρ_min = −0.92 e Å⁻³

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

	x	y	z	U_iso*/U_eq
I1	0.50557 (2)	0.49256 (3)	0.65599 (2)	0.03452 (13)
I2	0.39523 (2)	0.69922 (3)	0.70308 (2)	0.03321 (12)
Cu1	0.42457 (5)	0.53083 (6)	0.71218 (5)	0.0394 (2)
Cu2	0.49587 (5)	0.65787 (6)	0.67853 (5)	0.0381 (2)
P1	0.33129 (9)	0.45435 (12)	0.66404 (9)	0.0316 (4)
P2	0.51053 (10)	0.72918 (12)	0.59690 (10)	0.0360 (4)
C1	0.2712 (2)	0.4907 (3)	0.58054 (19)	0.0334 (16)
C2	0.2911 (2)	0.5474 (3)	0.5445 (2)	0.046 (2)
H2	0.3349	0.5672	0.5636	0.055*
C3	0.2467 (3)	0.5752 (3)	0.4806 (2)	0.064 (3)
H3	0.2603	0.6140	0.4560	0.076*
C4	0.1825 (3)	0.5463 (4)	0.4526 (2)	0.064 (3)
H4	0.1522	0.5653	0.4089	0.076*
C5	0.1626 (2)	0.4896 (4)	0.4886 (3)	0.056 (2)
H5	0.1187	0.4698	0.4695	0.068*
C6	0.2069 (2)	0.4618 (3)	0.5526 (2)	0.050 (2)
H6	0.1934	0.4230	0.5772	0.060*
C7	0.2815 (3)	0.4538 (3)	0.7114 (3)	0.0413 (18)
C8	0.2564 (3)	0.5324 (3)	0.7178 (3)	0.053 (2)
H8	0.2666	0.5822	0.6997	0.063*
C9	0.2163 (3)	0.5379 (4)	0.7505 (3)	0.071 (3)
H9	0.1991	0.5916	0.7549	0.085*
C10	0.2013 (3)	0.4650 (5)	0.7769 (3)	0.078 (3)
H10	0.1740	0.4688	0.7993	0.094*
C11	0.2265 (3)	0.3864 (4)	0.7706 (3)	0.061 (3)
H11	0.2162	0.3365	0.7886	0.073*
C12	0.2665 (3)	0.3808 (3)	0.7378 (3)	0.059 (2)
H12	0.2837	0.3271	0.7335	0.071*
C13	0.3412 (3)	0.3405 (4)	0.6489 (3)	0.0362 (16)
H13	0.3001	0.3109	0.6426	0.043*
C14	0.3493 (5)	0.3264 (4)	0.5848 (3)	0.056 (2)
H14A	0.3879	0.3585	0.5878	0.067*
H14B	0.3103	0.3487	0.5455	0.067*
C15	0.3578 (5)	0.2322 (5)	0.5734 (3)	0.063 (3)
H15A	0.3662	0.2259	0.5330	0.075*
H15B	0.3170	0.2012	0.5645	0.075*
C16	0.4143 (5)	0.1931 (6)	0.6349 (4)	0.077 (3)
H16A	0.4171	0.1313	0.6272	0.093*
H16B	0.4559	0.2200	0.6412	0.093*
C17	0.4044 (4)	0.2062 (4)	0.6986 (3)	0.051 (2)
H17A	0.3648	0.1748	0.6939	0.061*
H17B	0.4423	0.1826	0.7383	0.061*
C18	0.3967 (4)	0.3002 (4)	0.7104 (3)	0.0455 (19)
H18A	0.4381	0.3304	0.7200	0.055*
H18B	0.3879	0.3065	0.7505	0.055*
C19	0.5802 (2)	0.6838 (3)	0.5874 (3)	0.045 (2)
C20	0.5708 (3)	0.6110 (3)	0.5480 (3)	0.055 (2)
H20	0.5281	0.5886	0.5230	0.066*
C21	0.6240 (4)	0.5710 (3)	0.5451 (3)	0.070 (3)
H21	0.6176	0.5212	0.5181	0.084*
C22	0.6866 (3)	0.6037 (4)	0.5816 (4)	0.081 (4)
H22	0.7229	0.5764	0.5797	0.097*
C23	0.6959 (2)	0.6765 (4)	0.6210 (3)	0.072 (3)
H23	0.7387	0.6989	0.6460	0.086*
C24	0.6427 (3)	0.7166 (3)	0.6239 (3)	0.048 (2)
H24	0.6491	0.7663	0.6509	0.057*
C25	0.5256 (3)	0.8451 (2)	0.6111 (3)	0.047 (2)
C26	0.5547 (3)	0.8937 (3)	0.5788 (3)	0.0433 (19)
H26	0.5708	0.8668	0.5504	0.052*
C27	0.5602 (3)	0.9816 (3)	0.5881 (3)	0.054 (2)
H27	0.5801	1.0147	0.5661	0.065*
C28	0.5366 (3)	1.0209 (2)	0.6297 (3)	0.048 (2)
H28	0.5404	1.0810	0.6361	0.057*
C29	0.5075 (3)	0.9724 (3)	0.6620 (3)	0.052 (2)
H29	0.4913	0.9993	0.6904	0.062*
C30	0.5019 (3)	0.8845 (3)	0.6526 (3)	0.0422 (19)
H30	0.4820	0.8513	0.6747	0.051*
C31	0.4444 (3)	0.7277 (6)	0.5117 (3)	0.051 (2)
H31	0.4358	0.6652	0.5034	0.062*
C32	0.4591 (4)	0.7531 (6)	0.4546 (3)	0.060 (3)
H32A	0.4936	0.7148	0.4543	0.072*
H32B	0.4770	0.8117	0.4631	0.072*
C33	0.4022 (4)	0.7507 (6)	0.3855 (3)	0.068 (3)
H33A	0.4137	0.7838	0.3539	0.081*
H33B	0.3949	0.6909	0.3695	0.081*
C34	0.3397 (4)	0.7850 (6)	0.3821 (4)	0.074 (3)
H34A	0.3035	0.7676	0.3384	0.088*
H34B	0.3418	0.8481	0.3826	0.088*
C35	0.3240 (3)	0.7565 (7)	0.4384 (4)	0.075 (3)
H35A	0.2887	0.7930	0.4387	0.090*
H35C	0.3072	0.6973	0.4291	0.090*
C36	0.3807 (3)	0.7593 (6)	0.5073 (3)	0.052 (2)
H36C	0.3867	0.8191	0.5236	0.062*
H36A	0.3696	0.7250	0.5387	0.062*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1	0.0349 (3)	0.0310 (2)	0.0335 (2)	−0.0004 (2)	0.0113 (2)	−0.00226 (19)
I2	0.0356 (3)	0.0336 (2)	0.0289 (2)	0.0052 (2)	0.01262 (19)	0.00124 (19)
Cu1	0.0346 (5)	0.0368 (5)	0.0397 (5)	−0.0026 (4)	0.0099 (4)	−0.0012 (4)
Cu2	0.0452 (6)	0.0348 (5)	0.0365 (5)	−0.0001 (4)	0.0199 (4)	0.0016 (4)
P1	0.0307 (10)	0.0329 (9)	0.0297 (9)	0.0001 (8)	0.0118 (8)	−0.0014 (8)
P2	0.0447 (12)	0.0320 (10)	0.0338 (10)	−0.0043 (9)	0.0196 (9)	−0.0018 (8)
C1	0.033 (4)	0.035 (4)	0.028 (3)	0.002 (3)	0.010 (3)	−0.002 (3)
C2	0.051 (5)	0.054 (5)	0.030 (4)	0.000 (4)	0.016 (4)	0.004 (4)
C3	0.087 (8)	0.063 (6)	0.039 (5)	0.011 (6)	0.026 (5)	0.015 (4)
C4	0.065 (7)	0.076 (7)	0.032 (4)	0.027 (5)	0.004 (4)	−0.005 (4)
C5	0.038 (5)	0.071 (6)	0.049 (5)	0.003 (5)	0.009 (4)	−0.014 (5)
C6	0.047 (5)	0.056 (5)	0.034 (4)	−0.001 (4)	0.006 (4)	−0.001 (4)
C7	0.043 (5)	0.052 (5)	0.034 (4)	−0.003 (4)	0.021 (4)	−0.004 (4)
C8	0.063 (6)	0.054 (5)	0.050 (5)	0.003 (5)	0.033 (5)	−0.004 (4)
C9	0.082 (8)	0.078 (7)	0.066 (7)	0.010 (6)	0.044 (6)	−0.003 (6)
C10	0.071 (8)	0.109 (9)	0.080 (8)	0.009 (7)	0.055 (7)	0.000 (7)
C11	0.045 (5)	0.089 (7)	0.057 (6)	0.006 (5)	0.030 (5)	0.014 (5)
C12	0.066 (7)	0.064 (6)	0.059 (6)	0.005 (5)	0.038 (5)	0.005 (5)
C13	0.040 (4)	0.031 (4)	0.038 (4)	−0.002 (3)	0.018 (3)	−0.001 (3)
C14	0.069 (6)	0.052 (5)	0.036 (4)	0.009 (5)	0.013 (4)	−0.006 (4)
C15	0.076 (7)	0.048 (5)	0.051 (5)	0.011 (5)	0.016 (5)	−0.018 (4)
C16	0.094 (8)	0.058 (6)	0.062 (6)	0.032 (6)	0.017 (6)	−0.004 (5)
C17	0.043 (5)	0.045 (5)	0.063 (6)	0.015 (4)	0.022 (4)	0.015 (4)
C18	0.051 (5)	0.038 (4)	0.046 (5)	−0.001 (4)	0.021 (4)	0.001 (4)
C19	0.061 (6)	0.035 (4)	0.051 (5)	−0.002 (4)	0.036 (4)	−0.002 (4)
C20	0.078 (7)	0.049 (5)	0.051 (5)	−0.002 (5)	0.039 (5)	−0.005 (4)
C21	0.091 (9)	0.058 (6)	0.072 (7)	0.021 (6)	0.046 (7)	−0.005 (5)
C22	0.098 (10)	0.083 (8)	0.080 (8)	0.039 (7)	0.056 (8)	0.019 (7)
C23	0.060 (7)	0.060 (6)	0.103 (9)	0.001 (5)	0.041 (6)	0.004 (6)
C24	0.053 (5)	0.041 (4)	0.045 (5)	0.006 (4)	0.019 (4)	0.009 (4)
C25	0.062 (6)	0.036 (4)	0.048 (5)	−0.006 (4)	0.030 (4)	−0.003 (4)
C26	0.050 (5)	0.039 (4)	0.044 (5)	−0.008 (4)	0.023 (4)	−0.006 (4)
C27	0.075 (7)	0.038 (4)	0.060 (5)	−0.002 (4)	0.040 (5)	0.008 (4)
C28	0.048 (5)	0.034 (4)	0.056 (5)	−0.012 (4)	0.017 (4)	−0.007 (4)
C29	0.074 (6)	0.035 (4)	0.060 (5)	0.006 (4)	0.042 (5)	−0.002 (4)
C30	0.059 (5)	0.035 (4)	0.045 (5)	−0.006 (4)	0.034 (4)	0.000 (3)
C31	0.053 (5)	0.064 (6)	0.033 (4)	−0.013 (5)	0.016 (4)	0.001 (4)
C32	0.088 (8)	0.049 (5)	0.039 (5)	−0.001 (5)	0.024 (5)	−0.001 (4)
C33	0.089 (8)	0.055 (6)	0.054 (6)	−0.020 (6)	0.027 (6)	0.004 (5)
C34	0.100 (9)	0.050 (6)	0.042 (5)	−0.003 (6)	0.005 (5)	−0.004 (4)
C35	0.057 (6)	0.084 (8)	0.067 (7)	0.003 (6)	0.010 (5)	0.024 (6)
C36	0.059 (6)	0.047 (5)	0.042 (5)	−0.008 (4)	0.015 (4)	−0.007 (4)

Geometric parameters (Å, º) top

I1—Cu1	2.6976 (11)	C15—H15A	0.9900
I1—Cu1ⁱ	2.6849 (10)	C15—H15B	0.9900
I1—Cu2	2.6645 (10)	C16—C17	1.523 (8)
I2—Cu2	2.6543 (11)	C16—H16A	0.9900
I2—Cu1	2.7077 (10)	C16—H16B	0.9900
I2—Cu2ⁱ	2.7667 (11)	C17—C18	1.519 (7)
Cu1—P1	2.257 (2)	C17—H17A	0.9900
Cu1—I1ⁱ	2.6849 (10)	C17—H17B	0.9900
Cu1—Cu2	2.8631 (13)	C18—H18A	0.9900
Cu1—Cu2ⁱ	3.0292 (13)	C18—H18B	0.9900
Cu2—P2	2.256 (2)	C19—C20	1.3900
Cu2—I2ⁱ	2.7667 (11)	C19—C24	1.3900
Cu2—Cu1ⁱ	3.0292 (13)	C20—C21	1.3900
Cu2—Cu2ⁱ	3.0570 (18)	C20—H20	0.9500
P1—C1	1.830 (4)	C21—C22	1.3900
P1—C7	1.844 (4)	C21—H21	0.9500
P1—C13	1.846 (6)	C22—C23	1.3900
P2—C31	1.814 (7)	C22—H22	0.9500
P2—C19	1.831 (5)	C23—C24	1.3900
P2—C25	1.849 (4)	C23—H23	0.9500
C1—C2	1.3900	C24—H24	0.9500
C1—C6	1.3900	C25—C26	1.3900
C2—C3	1.3900	C25—C30	1.3900
C2—H2	0.9500	C26—C27	1.3900
C3—C4	1.3900	C26—H26	0.9500
C3—H3	0.9500	C27—C28	1.3900
C4—C5	1.3900	C27—H27	0.9500
C4—H4	0.9500	C28—C29	1.3900
C5—C6	1.3900	C28—H28	0.9500
C5—H5	0.9500	C29—C30	1.3900
C6—H6	0.9500	C29—H29	0.9500
C7—C8	1.3900	C30—H30	0.9500
C7—C12	1.3900	C31—C32	1.485 (7)
C8—C9	1.3900	C31—C36	1.494 (7)
C8—H8	0.9500	C31—H31	1.0000
C9—C10	1.3900	C32—C33	1.500 (7)
C9—H9	0.9500	C32—H32A	0.9900
C10—C11	1.3900	C32—H32B	0.9900
C10—H10	0.9500	C33—C34	1.491 (8)
C11—C12	1.3900	C33—H33A	0.9900
C11—H11	0.9500	C33—H33B	0.9900
C12—H12	0.9500	C34—C35	1.496 (8)
C13—C14	1.511 (7)	C34—H34A	0.9900
C13—C18	1.523 (7)	C34—H34B	0.9900
C13—H13	1.0000	C35—C36	1.496 (7)
C14—C15	1.523 (7)	C35—H35A	0.9900
C14—H14A	0.9900	C35—H35C	0.9900
C14—H14B	0.9900	C36—H36C	0.9900
C15—C16	1.526 (8)	C36—H36A	0.9900

Cu1ⁱ—I1—Cu1	70.07 (4)	C13—C14—H14B	109.3
Cu2—I1—Cu1ⁱ	68.98 (3)	C15—C14—H14B	109.3
Cu2—I1—Cu1	64.54 (3)	H14A—C14—H14B	107.9
Cu2—I2—Cu1	64.54 (3)	C14—C15—C16	111.3 (6)
Cu2—I2—Cu2ⁱ	68.62 (3)	C14—C15—H15A	109.4
Cu1—I2—Cu2ⁱ	67.18 (3)	C16—C15—H15A	109.4
P1—Cu1—I1ⁱ	112.08 (6)	C14—C15—H15B	109.4
P1—Cu1—I1	111.11 (6)	C16—C15—H15B	109.4
I1ⁱ—Cu1—I1	103.98 (3)	H15A—C15—H15B	108.0
P1—Cu1—I2	109.39 (6)	C17—C16—C15	110.4 (6)
I1ⁱ—Cu1—I2	107.90 (3)	C17—C16—H16A	109.6
I1—Cu1—I2	112.27 (4)	C15—C16—H16A	109.6
P1—Cu1—Cu2	140.58 (6)	C17—C16—H16B	109.6
I1ⁱ—Cu1—Cu2	107.34 (4)	C15—C16—H16B	109.6
I1—Cu1—Cu2	57.17 (3)	H16A—C16—H16B	108.1
I2—Cu1—Cu2	56.83 (3)	C18—C17—C16	111.1 (5)
P1—Cu1—Cu2ⁱ	146.32 (7)	C18—C17—H17A	109.4
I1ⁱ—Cu1—Cu2ⁱ	55.19 (3)	C16—C17—H17A	109.4
I1—Cu1—Cu2ⁱ	102.49 (4)	C18—C17—H17B	109.4
I2—Cu1—Cu2ⁱ	57.34 (3)	C16—C17—H17B	109.4
Cu2—Cu1—Cu2ⁱ	62.43 (4)	H17A—C17—H17B	108.0
P2—Cu2—I2	118.81 (7)	C17—C18—C13	111.4 (5)
P2—Cu2—I1	106.33 (6)	C17—C18—H18A	109.4
I2—Cu2—I1	115.10 (4)	C13—C18—H18A	109.4
P2—Cu2—I2ⁱ	104.17 (6)	C17—C18—H18B	109.4
I2—Cu2—I2ⁱ	104.49 (3)	C13—C18—H18B	109.4
I1—Cu2—I2ⁱ	106.78 (4)	H18A—C18—H18B	108.0
P2—Cu2—Cu1	147.91 (7)	C20—C19—C24	120.0
I2—Cu2—Cu1	58.64 (3)	C20—C19—P2	119.1 (3)
I1—Cu2—Cu1	58.29 (3)	C24—C19—P2	120.7 (3)
I2ⁱ—Cu2—Cu1	107.27 (4)	C19—C20—C21	120.0
P2—Cu2—Cu1ⁱ	135.06 (7)	C19—C20—H20	120.0
I2—Cu2—Cu1ⁱ	105.64 (4)	C21—C20—H20	120.0
I1—Cu2—Cu1ⁱ	55.83 (3)	C20—C21—C22	120.0
I2ⁱ—Cu2—Cu1ⁱ	55.48 (3)	C20—C21—H21	120.0
Cu1—Cu2—Cu1ⁱ	63.18 (4)	C22—C21—H21	120.0
P2—Cu2—Cu2ⁱ	148.19 (6)	C23—C22—C21	120.0
I2—Cu2—Cu2ⁱ	57.43 (3)	C23—C22—H22	120.0
I1—Cu2—Cu2ⁱ	102.56 (2)	C21—C22—H22	120.0
I2ⁱ—Cu2—Cu2ⁱ	53.95 (3)	C22—C23—C24	120.0
Cu1—Cu2—Cu2ⁱ	61.45 (3)	C22—C23—H23	120.0
Cu1ⁱ—Cu2—Cu2ⁱ	56.12 (3)	C24—C23—H23	120.0
C1—P1—C7	101.0 (3)	C23—C24—C19	120.0
C1—P1—C13	102.6 (3)	C23—C24—H24	120.0
C7—P1—C13	104.6 (3)	C19—C24—H24	120.0
C1—P1—Cu1	116.07 (18)	C26—C25—C30	120.0
C7—P1—Cu1	115.1 (2)	C26—C25—P2	123.1 (3)
C13—P1—Cu1	115.6 (2)	C30—C25—P2	116.7 (3)
C31—P2—C19	104.2 (3)	C27—C26—C25	120.0
C31—P2—C25	101.2 (4)	C27—C26—H26	120.0
C19—P2—C25	107.2 (3)	C25—C26—H26	120.0
C31—P2—Cu2	117.8 (3)	C28—C27—C26	120.0
C19—P2—Cu2	109.6 (2)	C28—C27—H27	120.0
C25—P2—Cu2	115.74 (18)	C26—C27—H27	120.0
C2—C1—C6	120.0	C27—C28—C29	120.0
C2—C1—P1	118.7 (3)	C27—C28—H28	120.0
C6—C1—P1	121.3 (3)	C29—C28—H28	120.0
C3—C2—C1	120.0	C30—C29—C28	120.0
C3—C2—H2	120.0	C30—C29—H29	120.0
C1—C2—H2	120.0	C28—C29—H29	120.0
C4—C3—C2	120.0	C29—C30—C25	120.0
C4—C3—H3	120.0	C29—C30—H30	120.0
C2—C3—H3	120.0	C25—C30—H30	120.0
C5—C4—C3	120.0	C32—C31—C36	115.4 (5)
C5—C4—H4	120.0	C32—C31—P2	118.2 (5)
C3—C4—H4	120.0	C36—C31—P2	113.9 (5)
C4—C5—C6	120.0	C32—C31—H31	101.9
C4—C5—H5	120.0	C36—C31—H31	101.9
C6—C5—H5	120.0	P2—C31—H31	101.9
C5—C6—C1	120.0	C31—C32—C33	115.5 (6)
C5—C6—H6	120.0	C31—C32—H32A	108.4
C1—C6—H6	120.0	C33—C32—H32A	108.4
C8—C7—C12	120.0	C31—C32—H32B	108.4
C8—C7—P1	115.7 (3)	C33—C32—H32B	108.4
C12—C7—P1	124.2 (3)	H32A—C32—H32B	107.5
C9—C8—C7	120.0	C34—C33—C32	115.1 (6)
C9—C8—H8	120.0	C34—C33—H33A	108.5
C7—C8—H8	120.0	C32—C33—H33A	108.5
C10—C9—C8	120.0	C34—C33—H33B	108.5
C10—C9—H9	120.0	C32—C33—H33B	108.5
C8—C9—H9	120.0	H33A—C33—H33B	107.5
C9—C10—C11	120.0	C33—C34—C35	114.8 (6)
C9—C10—H10	120.0	C33—C34—H34A	108.6
C11—C10—H10	120.0	C35—C34—H34A	108.6
C10—C11—C12	120.0	C33—C34—H34B	108.6
C10—C11—H11	120.0	C35—C34—H34B	108.6
C12—C11—H11	120.0	H34A—C34—H34B	107.6
C11—C12—C7	120.0	C36—C35—C34	114.3 (6)
C11—C12—H12	120.0	C36—C35—H35A	108.7
C7—C12—H12	120.0	C34—C35—H35A	108.7
C14—C13—C18	111.7 (5)	C36—C35—H35C	108.7
C14—C13—P1	112.6 (4)	C34—C35—H35C	108.7
C18—C13—P1	111.2 (4)	H35A—C35—H35C	107.6
C14—C13—H13	107.0	C31—C36—C35	115.9 (5)
C18—C13—H13	107.0	C31—C36—H36C	108.3
P1—C13—H13	107.0	C35—C36—H36C	108.3
C13—C14—C15	111.8 (6)	C31—C36—H36A	108.3
C13—C14—H14A	109.3	C35—C36—H36A	108.3
C15—C14—H14A	109.3	H36C—C36—H36A	107.4

Cu2—I1—Cu1—P1	137.42 (7)	I2—Cu2—P2—C25	62.0 (2)
Cu1ⁱ—I1—Cu1—P1	−147.05 (6)	I1—Cu2—P2—C25	−166.3 (2)
Cu2—I1—Cu1—I1ⁱ	−101.82 (4)	I2ⁱ—Cu2—P2—C25	−53.7 (2)
Cu1ⁱ—I1—Cu1—I1ⁱ	−26.29 (4)	Cu1—Cu2—P2—C25	138.1 (2)
Cu2—I1—Cu1—I2	14.56 (3)	Cu1ⁱ—Cu2—P2—C25	−108.6 (2)
Cu1ⁱ—I1—Cu1—I2	90.08 (3)	Cu2ⁱ—Cu2—P2—C25	−11.8 (3)
Cu1ⁱ—I1—Cu1—Cu2	75.53 (3)	C7—P1—C1—C2	140.6 (3)
Cu2—I1—Cu1—Cu2ⁱ	−45.01 (4)	C13—P1—C1—C2	−111.6 (4)
Cu1ⁱ—I1—Cu1—Cu2ⁱ	30.52 (4)	Cu1—P1—C1—C2	15.5 (4)
Cu2—I2—Cu1—P1	−138.44 (7)	C7—P1—C1—C6	−40.3 (4)
Cu2ⁱ—I2—Cu1—P1	145.31 (7)	C13—P1—C1—C6	67.5 (4)
Cu2—I2—Cu1—I1ⁱ	99.38 (4)	Cu1—P1—C1—C6	−165.4 (2)
Cu2ⁱ—I2—Cu1—I1ⁱ	23.13 (3)	C6—C1—C2—C3	0.0
Cu2—I2—Cu1—I1	−14.61 (3)	P1—C1—C2—C3	179.1 (4)
Cu2ⁱ—I2—Cu1—I1	−90.86 (4)	C1—C2—C3—C4	0.0
Cu2ⁱ—I2—Cu1—Cu2	−76.25 (4)	C2—C3—C4—C5	0.0
Cu2—I2—Cu1—Cu2ⁱ	76.25 (4)	C3—C4—C5—C6	0.0
Cu1—I2—Cu2—P2	142.86 (8)	C4—C5—C6—C1	0.0
Cu2ⁱ—I2—Cu2—P2	−143.09 (7)	C2—C1—C6—C5	0.0
Cu1—I2—Cu2—I1	15.13 (3)	P1—C1—C6—C5	−179.1 (4)
Cu2ⁱ—I2—Cu2—I1	89.18 (3)	C1—P1—C7—C8	−61.8 (4)
Cu1—I2—Cu2—I2ⁱ	−101.63 (4)	C13—P1—C7—C8	−168.0 (3)
Cu2ⁱ—I2—Cu2—I2ⁱ	−27.58 (4)	Cu1—P1—C7—C8	64.0 (3)
Cu2ⁱ—I2—Cu2—Cu1	74.05 (3)	C1—P1—C7—C12	115.8 (4)
Cu1—I2—Cu2—Cu1ⁱ	−44.01 (4)	C13—P1—C7—C12	9.6 (4)
Cu2ⁱ—I2—Cu2—Cu1ⁱ	30.04 (4)	Cu1—P1—C7—C12	−118.4 (3)
Cu1—I2—Cu2—Cu2ⁱ	−74.05 (3)	C12—C7—C8—C9	0.0
Cu1ⁱ—I1—Cu2—P2	133.84 (7)	P1—C7—C8—C9	177.7 (4)
Cu1—I1—Cu2—P2	−148.96 (7)	C7—C8—C9—C10	0.0
Cu1ⁱ—I1—Cu2—I2	−92.39 (4)	C8—C9—C10—C11	0.0
Cu1—I1—Cu2—I2	−15.19 (3)	C9—C10—C11—C12	0.0
Cu1ⁱ—I1—Cu2—I2ⁱ	23.07 (3)	C10—C11—C12—C7	0.0
Cu1—I1—Cu2—I2ⁱ	100.27 (4)	C8—C7—C12—C11	0.0
Cu1ⁱ—I1—Cu2—Cu1	−77.20 (4)	P1—C7—C12—C11	−177.5 (5)
Cu1—I1—Cu2—Cu1ⁱ	77.20 (4)	C1—P1—C13—C14	46.0 (6)
Cu1ⁱ—I1—Cu2—Cu2ⁱ	−32.70 (4)	C7—P1—C13—C14	151.1 (5)
Cu1—I1—Cu2—Cu2ⁱ	44.50 (4)	Cu1—P1—C13—C14	−81.3 (6)
P1—Cu1—Cu2—P2	−14.99 (18)	C1—P1—C13—C18	172.3 (5)
I1ⁱ—Cu1—Cu2—P2	164.42 (12)	C7—P1—C13—C18	−82.7 (5)
I1—Cu1—Cu2—P2	68.70 (13)	Cu1—P1—C13—C18	45.0 (5)
I2—Cu1—Cu2—P2	−95.17 (13)	C18—C13—C14—C15	53.7 (9)
Cu2ⁱ—Cu1—Cu2—P2	−162.46 (14)	P1—C13—C14—C15	179.7 (6)
P1—Cu1—Cu2—I2	80.18 (10)	C13—C14—C15—C16	−54.8 (11)
I1ⁱ—Cu1—Cu2—I2	−100.41 (4)	C14—C15—C16—C17	56.0 (11)
I1—Cu1—Cu2—I2	163.87 (4)	C15—C16—C17—C18	−56.7 (10)
Cu2ⁱ—Cu1—Cu2—I2	−67.29 (3)	C16—C17—C18—C13	55.9 (9)
P1—Cu1—Cu2—I1	−83.69 (10)	C14—C13—C18—C17	−54.3 (8)
I1ⁱ—Cu1—Cu2—I1	95.73 (4)	P1—C13—C18—C17	179.0 (5)
I2—Cu1—Cu2—I1	−163.87 (4)	C31—P2—C19—C20	−44.7 (4)
Cu2ⁱ—Cu1—Cu2—I1	128.84 (4)	C25—P2—C19—C20	−151.5 (3)
P1—Cu1—Cu2—I2ⁱ	176.92 (9)	Cu2—P2—C19—C20	82.2 (3)
I1ⁱ—Cu1—Cu2—I2ⁱ	−3.67 (5)	C31—P2—C19—C24	141.2 (4)
I1—Cu1—Cu2—I2ⁱ	−99.39 (4)	C25—P2—C19—C24	34.5 (4)
I2—Cu1—Cu2—I2ⁱ	96.74 (4)	Cu2—P2—C19—C24	−91.8 (3)
Cu2ⁱ—Cu1—Cu2—I2ⁱ	29.45 (3)	C24—C19—C20—C21	0.0
P1—Cu1—Cu2—Cu1ⁱ	−148.38 (11)	P2—C19—C20—C21	−174.1 (4)
I1ⁱ—Cu1—Cu2—Cu1ⁱ	31.03 (4)	C19—C20—C21—C22	0.0
I1—Cu1—Cu2—Cu1ⁱ	−64.69 (3)	C20—C21—C22—C23	0.0
I2—Cu1—Cu2—Cu1ⁱ	131.44 (4)	C21—C22—C23—C24	0.0
Cu2ⁱ—Cu1—Cu2—Cu1ⁱ	64.15 (4)	C22—C23—C24—C19	0.0
P1—Cu1—Cu2—Cu2ⁱ	147.47 (11)	C20—C19—C24—C23	0.0
I1ⁱ—Cu1—Cu2—Cu2ⁱ	−33.12 (4)	P2—C19—C24—C23	174.0 (4)
I1—Cu1—Cu2—Cu2ⁱ	−128.84 (4)	C31—P2—C25—C26	−71.7 (4)
I2—Cu1—Cu2—Cu2ⁱ	67.29 (3)	C19—P2—C25—C26	37.2 (4)
I1ⁱ—Cu1—P1—C1	166.9 (2)	Cu2—P2—C25—C26	159.8 (3)
I1—Cu1—P1—C1	−77.2 (2)	C31—P2—C25—C30	103.8 (4)
I2—Cu1—P1—C1	47.3 (2)	C19—P2—C25—C30	−147.3 (3)
Cu2—Cu1—P1—C1	−13.7 (2)	Cu2—P2—C25—C30	−24.7 (4)
Cu2ⁱ—Cu1—P1—C1	107.0 (2)	C30—C25—C26—C27	0.0
I1ⁱ—Cu1—P1—C7	49.3 (2)	P2—C25—C26—C27	175.4 (5)
I1—Cu1—P1—C7	165.2 (2)	C25—C26—C27—C28	0.0
I2—Cu1—P1—C7	−70.3 (2)	C26—C27—C28—C29	0.0
Cu2—Cu1—P1—C7	−131.3 (2)	C27—C28—C29—C30	0.0
Cu2ⁱ—Cu1—P1—C7	−10.6 (3)	C28—C29—C30—C25	0.0
I1ⁱ—Cu1—P1—C13	−72.9 (2)	C26—C25—C30—C29	0.0
I1—Cu1—P1—C13	43.0 (2)	P2—C25—C30—C29	−175.6 (4)
I2—Cu1—P1—C13	167.5 (2)	C19—P2—C31—C32	−41.9 (8)
Cu2—Cu1—P1—C13	106.5 (2)	C25—P2—C31—C32	69.2 (7)
Cu2ⁱ—Cu1—P1—C13	−132.7 (2)	Cu2—P2—C31—C32	−163.6 (6)
I2—Cu2—P2—C31	−57.8 (3)	C19—P2—C31—C36	177.8 (6)
I1—Cu2—P2—C31	73.9 (3)	C25—P2—C31—C36	−71.1 (6)
I2ⁱ—Cu2—P2—C31	−173.5 (3)	Cu2—P2—C31—C36	56.1 (7)
Cu1—Cu2—P2—C31	18.2 (4)	C36—C31—C32—C33	−40.0 (11)
Cu1ⁱ—Cu2—P2—C31	131.5 (3)	P2—C31—C32—C33	−179.8 (7)
Cu2ⁱ—Cu2—P2—C31	−131.6 (3)	C31—C32—C33—C34	42.1 (11)
I2—Cu2—P2—C19	−176.71 (19)	C32—C33—C34—C35	−44.2 (12)
I1—Cu2—P2—C19	−45.0 (2)	C33—C34—C35—C36	44.2 (12)
I2ⁱ—Cu2—P2—C19	67.6 (2)	C32—C31—C36—C35	40.6 (11)
Cu1—Cu2—P2—C19	−100.7 (2)	P2—C31—C36—C35	−177.9 (7)
Cu1ⁱ—Cu2—P2—C19	12.7 (2)	C34—C35—C36—C31	−42.5 (12)
Cu2ⁱ—Cu2—P2—C19	109.5 (2)

Symmetry code: (i) −x+1, y, −z+3/2.

Acknowledgements

ZSS acknowledges King Fahd University of Petroleum and Minerals, Dhahran, Saudi Arabia, for financial support.

References

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Volume 63| Part 3| March 2007| Pages m756-m758

https://doi.org/10.1107/S1600536807006204

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