μ-2,2′-Bipyrimidine-κ4N1,N1′:N3,N3′-bis­[iodido(triphenyl­phosphane-κP)copper(I)] dimethyl­formamide disolvate

Fettouhi, M.

doi:10.1107/S1600536812028139

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 7| July 2012| Page m1003

https://doi.org/10.1107/S1600536812028139

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μ-2,2′-Bipyrimidine-κ⁴N¹,N^1′:N³,N^3′-bis[iodido(triphenylphosphane-κP)copper(I)] dimethylformamide disolvate

Mohammed Fettouhi ^a ^*

^aDepartment of Chemistry, King Fahd University of Petroleum and Minerals, Dhahran 31261, Saudi Arabia
^*Correspondence e-mail: fettouhi@kfupm.edu.sa

(Received 7 June 2012; accepted 21 June 2012; online 30 June 2012)

In the title binuclear centrosymmetric complex, [Cu₂I₂(C₈H₆N₄)(C₁₈H₁₅P)₂]·2C₃H₇NO, the bis-bidentate 2,2′-bipyrimidine ligand bridges two copper(I) ions, each additionally bound to an iodide anion and a triphenylphosphane ligand in a distorted tetrahedral N₂IP geometry. The complex molecules pack in columns parallel to [100] generating cavities occupied by dimethylformamide solvent molecules. Weak C—H⋯I hydrogen-bonding interactions help to stabilize the crystal packing.

Related literature

For copper(I) mixed-ligand complexes based on diimines and phosphanes, see: Costa et al. (2011 ); Fazal et al. (2009 ). For 2,2′-bipyrimidine polymetallic complexes, see: Albores & Rentschler (2009 ); Yucesan et al. (2009 ). For the analogous chlorido complex, see: Tan et al. (2012 ).

Experimental

Crystal data

[Cu₂I₂(C₈H₆N₄)(C₁₈H₁₅P)₂]·2C₃H₇NO
M_r = 1209.78
Monoclinic, P 2₁ /c
a = 9.2436 (5) Å
b = 14.0911 (8) Å
c = 20.1932 (11) Å
β = 92.232 (1)°
V = 2628.2 (3) Å³
Z = 2
Mo Kα radiation
μ = 2.09 mm⁻¹
T = 298 K
0.70 × 0.17 × 0.14 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.323, T_max = 0.759
35525 measured reflections
6544 independent reflections
4457 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.114
S = 1.02
6544 reflections
291 parameters
H-atom parameters constrained
Δρ_max = 1.15 e Å⁻³
Δρ_min = −0.72 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Cu1—N3	2.075 (3)
Cu1—N4ⁱ	2.155 (3)
Cu1—P1	2.1857 (10)
Cu1—I1	2.5731 (6)

N3—Cu1—N4ⁱ	78.97 (10)
N3—Cu1—P1	124.71 (9)
N4ⁱ—Cu1—P1	119.53 (8)
N3—Cu1—I1	105.04 (9)
N4ⁱ—Cu1—I1	100.92 (8)
P1—Cu1—I1	119.15 (3)
Symmetry code: (i) -x, -y, -z+1.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯I1ⁱⁱ	0.93	3.03	3.796 (4)	140
Symmetry code: (ii) -x+1, -y, -z+1.

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536812028139/wm2646sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812028139/wm2646Isup2.hkl

checkCIF report

Comment top

Copper(I) mixed-ligand complexes based on diimines and phosphanes exhibit attracting photophysical and catalytic properties (Costa et al., 2011; Fazal et al., 2009). The 2,2'-bipyrimidine ligand (bpm) is of interest owing to its bis-chelating coordination ability, allowing the design of one-, two- and three-dimensional polymeric solids with interesting chemical and physical properties (Albores & Rentschler, 2009; Yucesan et al., 2009). Herein is reported on a bimetallic mixed-ligand copper(I) iodido complex based on 2,2'-bipyrimidine and triphenylphosphane, [Cu₂I₂{P(C₆H₅)₃}₂(C₈H₆N₄)]^.2(C₃H₇NO), (I).

The asymmetric unit of (I) contains one half-molecule of the complex [Cu₂I₂(Ph₃P)₂(bpm)] and one dimethylformamide solvent molecule. The complete complex is generated by inversion symmetry with the inversion centre being located on the central C—C bond of the bipyrimidine ligand. One bis-chelating bpm ligand bridges two Cu(I) ions which are each additionally bound to an iodide anion and a phosphorus atom of the phosphane ligand. The geometry around the metal ion is distorted tetrahedral (Figure 1). The triphenylphosphane ipso carbon atoms and the iodide anion adopt an anti configuration with respect to the rotation around the Cu—P bond with a torsion angle (C17—P1—Cu1—I1) of -163.2 (1) °. The unfavorable syn configuration is observed in the analogous chlorido complex reported recently which is likely stabilized by intra-molecular π—π interactions (Tan et al., 2012). The molecules of the complex (I) pack in columns parallel to [100] generating cavities occupied by the solvent molecules (Figure 2). Weak C—H···I hydrogen bonding interactions help to stabilize the crystal packing.

Related literature top

For copper(I) mixed-ligand complexes based on diimines and phosphanes, see: Costa et al. (2011); Fazal et al. (2009). For 2,2'-bipyrimidine polymetallic complexes, see: Albores & Rentschler (2009); Yucesan et al. (2009). For the analogous chlorido complex, see: Tan et al. (2012).

Experimental top

CuI (1.0 mmol, 0.1904 g), Ph₃P (1.0 mmol, 0.2623 g) and 2,2'-bipyrimidine (0.5 mmol, 0.0790 g) were reacted in dimethylformamide (35 ml) at 338 K for 2 h. The red solution was then filtered. After a few days, red crystals suitable for X-ray diffraction were obtained by slow evaporation.

Structure description top

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. Molecular structure of the title compound showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level (Symmetry code: i = -x,-y,-z + 1).
	Fig. 2. The packing of the structure of (I).

[(µ₂-2,2'-Bipyrimidine)diiodidobis(triphenylphosphane)dicopper(I) dimethylformamide] disolvate top

Crystal data top

[Cu₂I₂(C₈H₆N₄)(C₁₈H₁₅P)₂]·2C₃H₇NO	F(000) = 1204
M_r = 1209.78	D_x = 1.529 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 35525 reflections
a = 9.2436 (5) Å	θ = 1.8–28.3°
b = 14.0911 (8) Å	µ = 2.09 mm⁻¹
c = 20.1932 (11) Å	T = 298 K
β = 92.232 (1)°	Rod, red
V = 2628.2 (3) Å³	0.70 × 0.17 × 0.14 mm
Z = 2

Data collection top

Bruker SMART APEX CCD diffractometer	6544 independent reflections
Radiation source: normal-focus sealed tube	4457 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
ω scans	θ_max = 28.3°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
T_min = 0.323, T_max = 0.759	k = −18→18
35525 measured reflections	l = −26→26

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.114	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.047P)² + 1.9084P] where P = (F_o² + 2F_c²)/3
6544 reflections	(Δ/σ)_max = 0.002
291 parameters	Δρ_max = 1.15 e Å⁻³
0 restraints	Δρ_min = −0.72 e Å⁻³

Crystal data top

[Cu₂I₂(C₈H₆N₄)(C₁₈H₁₅P)₂]·2C₃H₇NO	V = 2628.2 (3) Å³
M_r = 1209.78	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.2436 (5) Å	µ = 2.09 mm⁻¹
b = 14.0911 (8) Å	T = 298 K
c = 20.1932 (11) Å	0.70 × 0.17 × 0.14 mm
β = 92.232 (1)°

Data collection top

Bruker SMART APEX CCD diffractometer	6544 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4457 reflections with I > 2σ(I)
T_min = 0.323, T_max = 0.759	R_int = 0.031
35525 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.114	H-atom parameters constrained
S = 1.02	Δρ_max = 1.15 e Å⁻³
6544 reflections	Δρ_min = −0.72 e Å⁻³
291 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

	x	y	z	U_iso*/U_eq
Cu1	0.21442 (4)	0.09166 (3)	0.42804 (2)	0.06482 (14)
P1	0.27705 (8)	0.23843 (6)	0.40902 (4)	0.0542 (2)
I1	0.33242 (3)	−0.04290 (2)	0.363020 (19)	0.09714 (15)
N3	0.1824 (3)	0.0354 (2)	0.52127 (15)	0.0613 (7)
N4	0.0105 (3)	−0.05172 (19)	0.58132 (14)	0.0566 (7)
N5	0.5546 (5)	0.1459 (3)	0.1663 (2)	0.0951 (11)
O1	0.7858 (7)	0.1074 (4)	0.1799 (6)	0.287 (5)
C1	0.0525 (3)	−0.0046 (2)	0.52828 (16)	0.0516 (7)
C2	0.1071 (4)	−0.0581 (3)	0.63210 (19)	0.0661 (9)
H2	0.0815	−0.0900	0.6702	0.079*
C3	0.2430 (4)	−0.0190 (3)	0.6297 (2)	0.0758 (11)
H3	0.3091	−0.0234	0.6654	0.091*
C4	0.2770 (4)	0.0266 (3)	0.5726 (2)	0.0756 (11)
H4	0.3691	0.0525	0.5695	0.091*
C5	0.4687 (3)	0.2596 (2)	0.39732 (18)	0.0581 (8)
C6	0.5653 (4)	0.2300 (3)	0.4476 (2)	0.0754 (10)
H6	0.5311	0.2007	0.4852	0.091*
C7	0.7126 (4)	0.2441 (4)	0.4418 (3)	0.0928 (14)
H7	0.7764	0.2251	0.4760	0.111*
C8	0.7651 (4)	0.2849 (3)	0.3872 (3)	0.0953 (15)
H8	0.8642	0.2942	0.3841	0.114*
C9	0.6737 (5)	0.3120 (4)	0.3372 (3)	0.0958 (14)
H9	0.7103	0.3387	0.2992	0.115*
C10	0.5233 (4)	0.3003 (3)	0.3420 (2)	0.0790 (11)
H10	0.4608	0.3203	0.3076	0.095*
C11	0.1831 (3)	0.2817 (3)	0.33385 (18)	0.0634 (9)
C12	0.1491 (4)	0.2157 (4)	0.2849 (2)	0.0829 (12)
H12	0.1803	0.1533	0.2900	0.099*
C13	0.0689 (6)	0.2418 (5)	0.2285 (3)	0.1131 (19)
H13	0.0463	0.1972	0.1958	0.136*
C14	0.0236 (6)	0.3329 (6)	0.2211 (3)	0.122 (2)
H14	−0.0302	0.3505	0.1832	0.146*
C15	0.0556 (6)	0.3986 (5)	0.2683 (3)	0.117 (2)
H15	0.0232	0.4607	0.2628	0.141*
C16	0.1362 (5)	0.3740 (4)	0.3249 (2)	0.0843 (12)
H16	0.1589	0.4197	0.3569	0.101*
C17	0.2317 (4)	0.3272 (3)	0.47079 (18)	0.0615 (8)
C18	0.3051 (5)	0.4121 (3)	0.4795 (2)	0.0875 (12)
H18	0.3856	0.4245	0.4547	0.105*
C19	0.2605 (7)	0.4787 (4)	0.5246 (3)	0.1106 (17)
H19	0.3113	0.5353	0.5301	0.133*
C20	0.1431 (7)	0.4616 (4)	0.5608 (3)	0.1070 (17)
H20	0.1131	0.5070	0.5907	0.128*
C21	0.0690 (5)	0.3794 (5)	0.5540 (2)	0.0994 (16)
H21	−0.0113	0.3687	0.5793	0.119*
C22	0.1124 (4)	0.3100 (3)	0.50876 (19)	0.0756 (11)
H22	0.0618	0.2532	0.5044	0.091*
C23	0.6841 (10)	0.1602 (6)	0.1610 (8)	0.267 (8)
H23	0.7095	0.2168	0.1407	0.321*
C24	0.4410 (7)	0.2140 (5)	0.1495 (4)	0.149 (2)
H24A	0.3958	0.2339	0.1892	0.223*
H24B	0.3701	0.1850	0.1200	0.223*
H24C	0.4821	0.2681	0.1283	0.223*
C25	0.5060 (11)	0.0608 (7)	0.1946 (5)	0.216 (5)
H25A	0.5801	0.0361	0.2244	0.324*
H25B	0.4848	0.0154	0.1601	0.324*
H25C	0.4202	0.0731	0.2184	0.324*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0474 (2)	0.0649 (3)	0.0820 (3)	−0.01234 (18)	0.00001 (19)	0.0069 (2)
P1	0.0421 (4)	0.0605 (5)	0.0600 (5)	−0.0076 (3)	0.0026 (3)	0.0019 (4)
I1	0.05444 (16)	0.0968 (2)	0.1387 (3)	0.00905 (13)	−0.01487 (16)	−0.03649 (19)
N3	0.0401 (13)	0.0681 (18)	0.0748 (19)	−0.0121 (12)	−0.0099 (12)	0.0072 (14)
N4	0.0402 (13)	0.0598 (16)	0.0692 (18)	−0.0035 (11)	−0.0050 (12)	0.0043 (13)
N5	0.083 (3)	0.093 (3)	0.109 (3)	−0.014 (2)	0.004 (2)	−0.006 (2)
O1	0.115 (4)	0.126 (5)	0.619 (17)	0.002 (4)	0.008 (7)	−0.049 (7)
C1	0.0363 (13)	0.0490 (17)	0.069 (2)	−0.0057 (12)	−0.0043 (13)	0.0022 (15)
C2	0.0516 (18)	0.078 (2)	0.068 (2)	−0.0042 (16)	−0.0060 (16)	0.0085 (18)
C3	0.0512 (19)	0.099 (3)	0.075 (3)	−0.0110 (19)	−0.0176 (17)	0.009 (2)
C4	0.0435 (17)	0.092 (3)	0.090 (3)	−0.0178 (17)	−0.0154 (18)	0.007 (2)
C5	0.0436 (15)	0.0559 (19)	0.075 (2)	−0.0051 (13)	0.0056 (15)	−0.0035 (16)
C6	0.0517 (19)	0.084 (3)	0.091 (3)	0.0005 (18)	0.0011 (18)	0.003 (2)
C7	0.048 (2)	0.101 (3)	0.129 (4)	0.005 (2)	−0.007 (2)	−0.002 (3)
C8	0.046 (2)	0.087 (3)	0.154 (5)	−0.005 (2)	0.016 (3)	−0.013 (3)
C9	0.068 (3)	0.099 (3)	0.123 (4)	−0.014 (2)	0.039 (3)	0.007 (3)
C10	0.059 (2)	0.092 (3)	0.087 (3)	−0.013 (2)	0.0123 (19)	0.008 (2)
C11	0.0408 (15)	0.085 (3)	0.064 (2)	−0.0089 (16)	0.0044 (14)	0.0097 (19)
C12	0.071 (2)	0.108 (3)	0.070 (3)	−0.010 (2)	−0.0067 (19)	0.000 (2)
C13	0.090 (3)	0.174 (6)	0.074 (3)	−0.019 (4)	−0.015 (3)	0.002 (4)
C14	0.078 (3)	0.199 (8)	0.087 (4)	0.006 (4)	−0.012 (3)	0.048 (5)
C15	0.097 (4)	0.145 (6)	0.110 (4)	0.031 (4)	0.016 (3)	0.054 (4)
C16	0.075 (3)	0.096 (3)	0.083 (3)	0.006 (2)	0.004 (2)	0.025 (2)
C17	0.0502 (17)	0.071 (2)	0.063 (2)	0.0037 (16)	−0.0012 (15)	0.0013 (17)
C18	0.077 (3)	0.080 (3)	0.106 (3)	−0.004 (2)	0.011 (2)	−0.019 (3)
C19	0.103 (4)	0.096 (4)	0.132 (5)	0.008 (3)	−0.003 (3)	−0.040 (3)
C20	0.102 (4)	0.115 (4)	0.104 (4)	0.032 (3)	−0.007 (3)	−0.031 (3)
C21	0.068 (3)	0.149 (5)	0.082 (3)	0.035 (3)	0.011 (2)	0.003 (3)
C22	0.0545 (19)	0.103 (3)	0.069 (2)	0.010 (2)	0.0022 (17)	−0.002 (2)
C23	0.107 (6)	0.104 (6)	0.60 (3)	−0.009 (5)	0.082 (10)	−0.038 (10)
C24	0.117 (5)	0.136 (6)	0.191 (7)	−0.015 (4)	−0.017 (5)	0.004 (5)
C25	0.198 (10)	0.212 (10)	0.236 (11)	−0.049 (8)	−0.003 (8)	0.103 (8)

Geometric parameters (Å, º) top

Cu1—N3	2.075 (3)	C9—H9	0.9300
Cu1—N4ⁱ	2.155 (3)	C10—H10	0.9300
Cu1—P1	2.1857 (10)	C11—C16	1.380 (6)
Cu1—I1	2.5731 (6)	C11—C12	1.385 (6)
P1—C5	1.821 (3)	C12—C13	1.384 (7)
P1—C11	1.824 (4)	C12—H12	0.9300
P1—C17	1.827 (4)	C13—C14	1.357 (9)
N3—C4	1.336 (5)	C13—H13	0.9300
N3—C1	1.339 (4)	C14—C15	1.354 (9)
N4—C1	1.331 (4)	C14—H14	0.9300
N4—C2	1.336 (4)	C15—C16	1.383 (7)
N4—Cu1ⁱ	2.155 (3)	C15—H15	0.9300
N5—C23	1.222 (8)	C16—H16	0.9300
N5—C25	1.408 (8)	C17—C18	1.383 (6)
N5—C24	1.453 (8)	C17—C22	1.388 (5)
O1—C23	1.247 (12)	C18—C19	1.381 (7)
C1—C1ⁱ	1.476 (6)	C18—H18	0.9300
C2—C3	1.374 (5)	C19—C20	1.354 (8)
C2—H2	0.9300	C19—H19	0.9300
C3—C4	1.367 (6)	C20—C21	1.349 (8)
C3—H3	0.9300	C20—H20	0.9300
C4—H4	0.9300	C21—C22	1.407 (7)
C5—C10	1.370 (5)	C21—H21	0.9300
C5—C6	1.390 (5)	C22—H22	0.9300
C6—C7	1.385 (5)	C23—H23	0.9300
C6—H6	0.9300	C24—H24A	0.9600
C7—C8	1.350 (7)	C24—H24B	0.9600
C7—H7	0.9300	C24—H24C	0.9600
C8—C9	1.346 (7)	C25—H25A	0.9600
C8—H8	0.9300	C25—H25B	0.9600
C9—C10	1.407 (5)	C25—H25C	0.9600

N3—Cu1—N4ⁱ	78.97 (10)	C16—C11—C12	118.5 (4)
N3—Cu1—P1	124.71 (9)	C16—C11—P1	124.2 (3)
N4ⁱ—Cu1—P1	119.53 (8)	C12—C11—P1	117.2 (3)
N3—Cu1—I1	105.04 (9)	C13—C12—C11	120.5 (5)
N4ⁱ—Cu1—I1	100.92 (8)	C13—C12—H12	119.7
P1—Cu1—I1	119.15 (3)	C11—C12—H12	119.7
C5—P1—C11	105.74 (16)	C14—C13—C12	119.7 (6)
C5—P1—C17	103.11 (16)	C14—C13—H13	120.2
C11—P1—C17	102.97 (17)	C12—C13—H13	120.2
C5—P1—Cu1	116.31 (12)	C15—C14—C13	120.8 (5)
C11—P1—Cu1	110.00 (13)	C15—C14—H14	119.6
C17—P1—Cu1	117.30 (12)	C13—C14—H14	119.6
C4—N3—C1	116.2 (3)	C14—C15—C16	120.4 (6)
C4—N3—Cu1	128.9 (2)	C14—C15—H15	119.8
C1—N3—Cu1	114.6 (2)	C16—C15—H15	119.8
C1—N4—C2	116.4 (3)	C11—C16—C15	120.1 (5)
C1—N4—Cu1ⁱ	111.74 (19)	C11—C16—H16	119.9
C2—N4—Cu1ⁱ	131.5 (2)	C15—C16—H16	119.9
C23—N5—C25	120.3 (8)	C18—C17—C22	118.5 (4)
C23—N5—C24	124.8 (7)	C18—C17—P1	123.7 (3)
C25—N5—C24	114.7 (6)	C22—C17—P1	117.7 (3)
N4—C1—N3	125.9 (3)	C19—C18—C17	120.9 (5)
N4—C1—C1ⁱ	117.6 (3)	C19—C18—H18	119.5
N3—C1—C1ⁱ	116.5 (4)	C17—C18—H18	119.5
N4—C2—C3	122.0 (4)	C20—C19—C18	120.0 (5)
N4—C2—H2	119.0	C20—C19—H19	120.0
C3—C2—H2	119.0	C18—C19—H19	120.0
C4—C3—C2	117.3 (3)	C21—C20—C19	120.8 (5)
C4—C3—H3	121.3	C21—C20—H20	119.6
C2—C3—H3	121.3	C19—C20—H20	119.6
N3—C4—C3	122.2 (3)	C20—C21—C22	120.4 (5)
N3—C4—H4	118.9	C20—C21—H21	119.8
C3—C4—H4	118.9	C22—C21—H21	119.8
C10—C5—C6	118.4 (3)	C17—C22—C21	119.3 (5)
C10—C5—P1	124.4 (3)	C17—C22—H22	120.4
C6—C5—P1	117.2 (3)	C21—C22—H22	120.4
C7—C6—C5	120.0 (4)	N5—C23—O1	127.1 (10)
C7—C6—H6	120.0	N5—C23—H23	116.4
C5—C6—H6	120.0	O1—C23—H23	116.4
C8—C7—C6	121.1 (4)	N5—C24—H24A	109.5
C8—C7—H7	119.5	N5—C24—H24B	109.5
C6—C7—H7	119.5	H24A—C24—H24B	109.5
C9—C8—C7	119.9 (4)	N5—C24—H24C	109.5
C9—C8—H8	120.1	H24A—C24—H24C	109.5
C7—C8—H8	120.1	H24B—C24—H24C	109.5
C8—C9—C10	120.5 (4)	N5—C25—H25A	109.5
C8—C9—H9	119.7	N5—C25—H25B	109.5
C10—C9—H9	119.7	H25A—C25—H25B	109.5
C5—C10—C9	120.1 (4)	N5—C25—H25C	109.5
C5—C10—H10	120.0	H25A—C25—H25C	109.5
C9—C10—H10	120.0	H25B—C25—H25C	109.5

Symmetry code: (i) −x, −y, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···I1ⁱⁱ	0.93	3.03	3.796 (4)	140

Symmetry code: (ii) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formula	[Cu₂I₂(C₈H₆N₄)(C₁₈H₁₅P)₂]·2C₃H₇NO
M_r	1209.78
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	9.2436 (5), 14.0911 (8), 20.1932 (11)
β (°)	92.232 (1)
V (Å³)	2628.2 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.09
Crystal size (mm)	0.70 × 0.17 × 0.14

Data collection
Diffractometer	Bruker SMART APEX CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.323, 0.759
No. of measured, independent and observed [I > 2σ(I)] reflections	35525, 6544, 4457
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.114, 1.02
No. of reflections	6544
No. of parameters	291
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.15, −0.72

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), publCIF (Westrip, 2010).

Selected geometric parameters (Å, º) top

Cu1—N3	2.075 (3)	Cu1—P1	2.1857 (10)
Cu1—N4ⁱ	2.155 (3)	Cu1—I1	2.5731 (6)

N3—Cu1—N4ⁱ	78.97 (10)	N3—Cu1—I1	105.04 (9)
N3—Cu1—P1	124.71 (9)	N4ⁱ—Cu1—I1	100.92 (8)
N4ⁱ—Cu1—P1	119.53 (8)	P1—Cu1—I1	119.15 (3)

Symmetry code: (i) −x, −y, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···I1ⁱⁱ	0.93	3.03	3.796 (4)	140

Symmetry code: (ii) −x+1, −y, −z+1.

Acknowledgements

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

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