μ-1,2-Bis­(diphenyl­phos­phino)­ethane-κ2P:P′-bis­{[1,2-bis­(diphenyl­phosphino)­ethane-κ2P,P′]bromidocopper(I)} acetone disolvate

Shi, W.-J.

doi:10.1107/S1600536808031000

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 10| October 2008| Pages m1346-m1347

doi:10.1107/S1600536808031000

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μ-1,2-Bis(diphenylphosphino)ethane-κ²P:P′-bis{[1,2-bis(diphenylphosphino)ethane-κ²P,P′]bromidocopper(I)} acetone disolvate

Wen-Juan Shi ^a ^*

^aJiangxi Key Laboratory of Surface Engineering, Jiangxi Science and Technology Normal University, Jiangxi 330013, People's Republic of China
^*Correspondence e-mail: swjuan2000@126.com

(Received 24 September 2008; accepted 25 September 2008; online 27 September 2008)

In the crystal structure of the title compound, [Cu₂Br₂(dppe)₃]·2CH₃COCH₃ [dppe is 1,2-bis(diphenylphosphino)ethane, C₂₆H₂₄P₂], the two Cu centers are bridged by a dppe ligand and each metal center carries one chelating dppe unit, with the fourth coordination site available for the Br⁻ anion. The molecule is centrosymmetric, with the center of symmetry located between the methylene C atoms of the bridging dppe ligand. The crystal structure is stabilized by intramolecular C—H⋯Br hydrogen bonds and intermolecular π–π interactions, with a centroid-to-centroid distance of 3.2055 (1) Å.

Related literature

For related research on phosphanecopper(I) compounds as biological agents, see: Berners-Price et al. (1987 ); Goldstein et al. (1992 ); Navon et al. (1995 ). For related structures, see: Albano et al. (1972 ); Comba et al. (1999 ); Darensbourg et al. (1990 ); Eller et al. (1977 ); Leoni et al. (1983 ); Mohr et al. (1991 ); Di Nicola et al. (2006 ).

Experimental

Crystal data

[Cu₂Br₂(C₂₆H₂₄P₂)₃]·2C₃H₆O
M_r = 1598.23
Monoclinic, P 2₁ /n
a = 12.5301 (6) Å
b = 21.8966 (10) Å
c = 14.8028 (7) Å
β = 105.932 (1)°
V = 3905.4 (3) Å³
Z = 2
Mo Kα radiation
μ = 1.74 mm⁻¹
T = 295 (2) K
0.20 × 0.18 × 0.17 mm

Data collection

Bruker SMART APEX area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.691, T_max = 0.752
33389 measured reflections
8907 independent reflections
6429 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.129
S = 1.02
8907 reflections
435 parameters
H-atom parameters constrained
Δρ_max = 0.75 e Å⁻³
Δρ_min = −0.42 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Cu1—P3	2.2740 (8)
Cu1—P1	2.2992 (8)
Cu1—P2	2.3205 (9)
Cu1—Br1	2.4381 (5)

P3—Cu1—P1	113.74 (3)
P3—Cu1—P2	122.23 (3)
P1—Cu1—P2	89.30 (3)
P3—Cu1—Br1	102.02 (3)
P1—Cu1—Br1	115.56 (3)
P2—Cu1—Br1	114.67 (3)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16⋯Br1	0.93	2.86	3.760 (4)	164
C32—H32⋯Br1ⁱ	0.93	2.82	3.666 (4)	151
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: SMART (Bruker, 2002 ); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808031000/sj2542sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808031000/sj2542Isup2.hkl

checkCIF report

Comment top

Detailed studies of solution equilibria and dynamics of copper(I) compounds of bidentate phosphanes have attracted considerable interest because of their potential application as potent antitumor agents (Berners-Price et al., 1987) and as free radical scavengers in industrial processes (Goldstein et al., 1992; Navon et al., 1995). Some mononuclear (Darensbourg et al., 1990; Leoni et al., 1983) and dinuclear phosphanecopper(I) compounds (Eller et al., 1977; Mohr et al., 1991) with coordinated and bridging halide anions and with phosphane ligands in various coordination modes have been isolated and characterized. In this work, 1,2-bis(diphenylphosphino)ethane (dppe) was adopted as a ligand which coordinates to the copper(I) ions in both bridging and chelating modes.

The asymmetric unit of the title compound (Fig. 1) consists of one half of the centrosymmetric dinuclear molecule Cu₂Br₂(dppe)₃ and an acetone solvate molecule. In the molecule Cu₂Br₂(dppe)₃, each copper(I) center adopts a distorted tetrahedral geometry due to the constraint imposed by a chelating dppe ligand with a P(1)—Cu(1)—P(2) angle of 89.30 (3)°, which is comparable to what has been observed in other similar structures (Albano et al., 1972; Comba et al., 1999). The copper(I)–phosphane distances are also in the range expected from other known structures (Albano et al., 1972; Comba et al., 1999; Di Nicola et al., 2006).

The title compound can be stablized by intramolecular C—H···Br hydrogen bonds between Br(1)^- anions and –CH groups from phenyl rings. Additionally, the structure is held intact through intermolecular π–π stacking interactions [centroid-to-centroid distance of 3.2055 (1) Å], displaying a one-dimensional supramolecular array (Fig. 2).

Related literature top

For related research on phosphanecopper(I) compounds as biological agents, see: Berners-Price et al. (1987); Goldstein et al. (1992); Navon et al. (1995). For related structures, see: Albano et al. (1972); Comba et al. (1999); Darensbourg et al. (1990); Eller et al. (1977); Leoni et al. (1983); Mohr et al. (1991); Di Nicola et al. (2006).

Experimental top

1,2-Bis(diphenylphosphino)ethane (40 mg, 0.1 mmol) was added to an acetone suspension (7 ml) of CuBr (10 mg, 0.07 mmol). After the addition, a precipitate slowly formed and the suspension was stirred for 12 h. The precipitate was filtered off and the resulting colorless filtrate was allowed to cool in a refrigerator. Colorless block shaped crystals were obtained after two weeks. Yield: 10 mg (20%).

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); 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

	Fig. 1. The molecular structure of (I), with displacement ellipsoids drawn at the 30% probability level. H atoms are omitted for clarity. [symmetry code: (A) -x + 1, -y + 1, -z + 1].
	Fig. 2. Packing diagram of the title structure showing the π–π stacking interactions.

µ-1,2-Bis(diphenylphosphino)ethane-κ²P:P'-bis{[1,2-bis(diphenylphosphino)ethane-κ²P,P']bromidocopper(I)} acetone disolvate top

Crystal data top

[Cu₂Br₂(C₂₆H₂₄P₂)₃]·2C₃H₆O	F(000) = 1644
M_r = 1598.23	D_x = 1.359 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6062 reflections
a = 12.5301 (6) Å	θ = 2.3–23.5°
b = 21.8966 (10) Å	µ = 1.74 mm⁻¹
c = 14.8028 (7) Å	T = 295 K
β = 105.932 (1)°	Block, colourless
V = 3905.4 (3) Å³	0.20 × 0.18 × 0.17 mm
Z = 2

Data collection top

Bruker SMART APEX area-detector diffractometer	8907 independent reflections
Radiation source: fine-focus sealed tube	6429 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
ϕ and ω scans	θ_max = 27.5°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −16→16
T_min = 0.691, T_max = 0.752	k = −28→28
33389 measured reflections	l = −19→19

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.129	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0643P)² + 1.6786P] where P = (F_o² + 2F_c²)/3
8907 reflections	(Δ/σ)_max = 0.001
435 parameters	Δρ_max = 0.75 e Å⁻³
0 restraints	Δρ_min = −0.42 e Å⁻³

Crystal data top

[Cu₂Br₂(C₂₆H₂₄P₂)₃]·2C₃H₆O	V = 3905.4 (3) Å³
M_r = 1598.23	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 12.5301 (6) Å	µ = 1.74 mm⁻¹
b = 21.8966 (10) Å	T = 295 K
c = 14.8028 (7) Å	0.20 × 0.18 × 0.17 mm
β = 105.932 (1)°

Data collection top

Bruker SMART APEX area-detector diffractometer	8907 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	6429 reflections with I > 2σ(I)
T_min = 0.691, T_max = 0.752	R_int = 0.035
33389 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.129	H-atom parameters constrained
S = 1.02	Δρ_max = 0.75 e Å⁻³
8907 reflections	Δρ_min = −0.42 e Å⁻³
435 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	0.37525 (3)	0.569117 (17)	0.27963 (2)	0.04207 (12)
Br1	0.43216 (4)	0.472630 (18)	0.22494 (3)	0.06925 (14)
P1	0.19903 (6)	0.57078 (4)	0.29823 (5)	0.04037 (18)
P2	0.32268 (6)	0.64379 (4)	0.16474 (5)	0.04127 (18)
P3	0.51111 (6)	0.58486 (4)	0.41525 (5)	0.04102 (19)
O1	0.6704 (6)	0.6982 (3)	0.0724 (5)	0.200 (2)
C1	0.0907 (3)	0.52128 (14)	0.2279 (2)	0.0460 (7)
C2	−0.0179 (3)	0.52408 (17)	0.2345 (3)	0.0589 (9)
H2	−0.0345	0.5479	0.2809	0.071*
C3	−0.1007 (3)	0.4917 (2)	0.1726 (3)	0.0726 (11)
H3	−0.1730	0.4937	0.1776	0.087*
C4	−0.0775 (4)	0.4568 (2)	0.1038 (3)	0.0771 (12)
H4	−0.1342	0.4356	0.0617	0.093*
C5	0.0292 (4)	0.4530 (2)	0.0968 (3)	0.0753 (12)
H5	0.0451	0.4290	0.0503	0.090*
C6	0.1137 (3)	0.48532 (16)	0.1596 (2)	0.0571 (9)
H6	0.1862	0.4825	0.1552	0.069*
C7	0.1730 (2)	0.57326 (15)	0.4131 (2)	0.0462 (7)
C8	0.1871 (4)	0.6258 (2)	0.4651 (3)	0.0743 (12)
H8	0.2035	0.6620	0.4388	0.089*
C9	0.1774 (4)	0.6263 (2)	0.5561 (3)	0.0931 (14)
H9	0.1868	0.6625	0.5902	0.112*
C10	0.1542 (4)	0.5734 (2)	0.5954 (3)	0.0840 (13)
H10	0.1466	0.5737	0.6562	0.101*
C11	0.1421 (4)	0.5207 (2)	0.5464 (3)	0.0732 (11)
H11	0.1280	0.4846	0.5741	0.088*
C12	0.1507 (3)	0.52019 (17)	0.4549 (3)	0.0583 (9)
H12	0.1414	0.4837	0.4215	0.070*
C13	0.1466 (3)	0.64480 (15)	0.2445 (2)	0.0500 (8)
H13A	0.0672	0.6476	0.2358	0.060*
H13B	0.1822	0.6780	0.2850	0.060*
C14	0.1726 (2)	0.64918 (15)	0.1491 (2)	0.0475 (7)
H14A	0.1453	0.6877	0.1193	0.057*
H14B	0.1352	0.6164	0.1085	0.057*
C15	0.3318 (3)	0.63429 (15)	0.0446 (2)	0.0470 (7)
C16	0.3772 (3)	0.58138 (18)	0.0207 (3)	0.0615 (9)
H16	0.4025	0.5511	0.0655	0.074*
C17	0.3851 (4)	0.5733 (2)	−0.0706 (3)	0.0768 (12)
H17	0.4163	0.5376	−0.0860	0.092*
C18	0.3486 (4)	0.6159 (3)	−0.1366 (3)	0.0796 (13)
H18	0.3539	0.6097	−0.1974	0.096*
C19	0.3035 (4)	0.6686 (2)	−0.1138 (3)	0.0823 (13)
H19	0.2784	0.6984	−0.1596	0.099*
C20	0.2945 (3)	0.67856 (19)	−0.0235 (2)	0.0662 (10)
H20	0.2637	0.7146	−0.0090	0.079*
C21	0.3690 (3)	0.72282 (16)	0.1894 (2)	0.0531 (8)
C22	0.4791 (3)	0.7350 (2)	0.1940 (3)	0.0744 (11)
H22	0.5254	0.7040	0.1840	0.089*
C23	0.5198 (5)	0.7950 (3)	0.2142 (4)	0.1008 (16)
H23	0.5935	0.8036	0.2176	0.121*
C24	0.4521 (6)	0.8405 (3)	0.2287 (4)	0.1076 (17)
H24	0.4797	0.8800	0.2412	0.129*
C25	0.3452 (5)	0.8287 (2)	0.2252 (3)	0.0970 (15)
H25	0.2997	0.8597	0.2364	0.116*
C26	0.3033 (4)	0.76971 (17)	0.2049 (3)	0.0718 (10)
H26	0.2294	0.7620	0.2017	0.086*
C27	0.4849 (3)	0.64567 (15)	0.4905 (2)	0.0475 (7)
C28	0.4577 (3)	0.70269 (16)	0.4509 (3)	0.0602 (9)
H28	0.4553	0.7085	0.3881	0.072*
C29	0.4343 (4)	0.75082 (19)	0.5011 (3)	0.0774 (12)
H29	0.4174	0.7889	0.4728	0.093*
C30	0.4358 (4)	0.7428 (2)	0.5926 (4)	0.0809 (13)
H30	0.4183	0.7752	0.6267	0.097*
C31	0.4630 (4)	0.6877 (2)	0.6339 (3)	0.0831 (13)
H31	0.4651	0.6825	0.6967	0.100*
C32	0.4880 (3)	0.63863 (18)	0.5832 (3)	0.0651 (10)
H32	0.5068	0.6010	0.6124	0.078*
C33	0.6459 (2)	0.60902 (15)	0.4006 (2)	0.0472 (7)
C34	0.6647 (3)	0.6054 (2)	0.3137 (3)	0.0666 (10)
H34	0.6106	0.5895	0.2630	0.080*
C35	0.7655 (4)	0.6258 (2)	0.3016 (3)	0.0855 (14)
H35	0.7780	0.6238	0.2426	0.103*
C36	0.8450 (4)	0.6485 (2)	0.3751 (4)	0.0830 (13)
H36	0.9117	0.6620	0.3662	0.100*
C37	0.8283 (3)	0.65166 (19)	0.4613 (4)	0.0785 (12)
H37	0.8838	0.6667	0.5118	0.094*
C38	0.7281 (3)	0.63241 (17)	0.4743 (3)	0.0627 (9)
H38	0.7162	0.6353	0.5335	0.075*
C39	0.5496 (2)	0.51720 (14)	0.4915 (2)	0.0455 (7)
H39A	0.5914	0.4894	0.4632	0.055*
H39B	0.5979	0.5300	0.5516	0.055*
C40	0.6595 (9)	0.6699 (4)	0.0016 (8)	0.188 (2)
C41	0.6260 (8)	0.6948 (4)	−0.0902 (6)	0.193 (2)
H41A	0.5854	0.7319	−0.0894	0.289*
H41B	0.5795	0.6661	−0.1320	0.289*
H41C	0.6903	0.7034	−0.1113	0.289*
C42	0.7128 (8)	0.6120 (4)	0.0087 (7)	0.198 (3)
H42A	0.7886	0.6160	0.0453	0.297*
H42B	0.7104	0.5975	−0.0530	0.297*
H42C	0.6752	0.5835	0.0387	0.297*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0368 (2)	0.0466 (2)	0.0328 (2)	0.00363 (15)	0.00805 (15)	−0.00058 (15)
Br1	0.0828 (3)	0.0659 (3)	0.0499 (2)	0.0296 (2)	0.0208 (2)	−0.00313 (17)
P1	0.0385 (4)	0.0433 (4)	0.0407 (4)	0.0002 (3)	0.0131 (3)	0.0015 (3)
P2	0.0408 (4)	0.0452 (4)	0.0372 (4)	−0.0033 (3)	0.0097 (3)	0.0021 (3)
P3	0.0370 (4)	0.0487 (5)	0.0363 (4)	0.0002 (3)	0.0081 (3)	0.0015 (3)
O1	0.242 (5)	0.196 (5)	0.182 (4)	−0.043 (4)	0.090 (4)	−0.045 (4)
C1	0.0458 (17)	0.0483 (18)	0.0425 (17)	−0.0066 (14)	0.0096 (14)	0.0054 (14)
C2	0.0463 (19)	0.067 (2)	0.062 (2)	−0.0061 (16)	0.0114 (16)	0.0013 (18)
C3	0.050 (2)	0.085 (3)	0.076 (3)	−0.015 (2)	0.0053 (19)	0.014 (2)
C4	0.074 (3)	0.083 (3)	0.060 (2)	−0.031 (2)	−0.005 (2)	0.002 (2)
C5	0.089 (3)	0.076 (3)	0.058 (2)	−0.023 (2)	0.014 (2)	−0.012 (2)
C6	0.059 (2)	0.062 (2)	0.051 (2)	−0.0112 (17)	0.0167 (17)	0.0006 (17)
C7	0.0359 (15)	0.059 (2)	0.0459 (17)	0.0012 (13)	0.0149 (13)	0.0025 (15)
C8	0.103 (3)	0.070 (3)	0.064 (2)	−0.018 (2)	0.046 (2)	−0.012 (2)
C9	0.124 (4)	0.097 (3)	0.071 (3)	−0.023 (3)	0.048 (3)	−0.029 (3)
C10	0.092 (3)	0.120 (4)	0.050 (2)	−0.010 (3)	0.036 (2)	−0.002 (2)
C11	0.078 (3)	0.085 (3)	0.062 (2)	0.004 (2)	0.029 (2)	0.021 (2)
C12	0.063 (2)	0.059 (2)	0.056 (2)	0.0033 (17)	0.0222 (17)	0.0058 (17)
C13	0.0466 (17)	0.0470 (18)	0.060 (2)	0.0072 (14)	0.0207 (15)	0.0049 (15)
C14	0.0435 (16)	0.0478 (18)	0.0487 (18)	0.0021 (13)	0.0084 (14)	0.0085 (14)
C15	0.0441 (17)	0.058 (2)	0.0376 (16)	−0.0107 (15)	0.0095 (13)	0.0012 (14)
C16	0.063 (2)	0.074 (2)	0.051 (2)	0.0039 (19)	0.0222 (17)	−0.0006 (18)
C17	0.081 (3)	0.099 (3)	0.060 (2)	−0.008 (2)	0.036 (2)	−0.013 (2)
C18	0.081 (3)	0.116 (4)	0.045 (2)	−0.023 (3)	0.023 (2)	−0.008 (2)
C19	0.088 (3)	0.110 (4)	0.045 (2)	−0.014 (3)	0.012 (2)	0.020 (2)
C20	0.075 (3)	0.072 (3)	0.046 (2)	−0.009 (2)	0.0075 (17)	0.0068 (18)
C21	0.067 (2)	0.0541 (19)	0.0369 (16)	−0.0173 (16)	0.0125 (15)	0.0035 (14)
C22	0.070 (2)	0.085 (3)	0.062 (2)	−0.029 (2)	0.0084 (19)	0.006 (2)
C23	0.099 (3)	0.113 (4)	0.084 (3)	−0.058 (3)	0.014 (3)	0.005 (3)
C24	0.152 (5)	0.083 (3)	0.087 (3)	−0.051 (3)	0.032 (3)	−0.019 (3)
C25	0.154 (4)	0.064 (3)	0.083 (3)	−0.020 (3)	0.049 (3)	−0.012 (2)
C26	0.105 (3)	0.050 (2)	0.065 (2)	−0.012 (2)	0.032 (2)	−0.0030 (18)
C27	0.0428 (17)	0.0547 (19)	0.0439 (17)	−0.0046 (14)	0.0100 (14)	−0.0057 (14)
C28	0.068 (2)	0.058 (2)	0.051 (2)	0.0054 (18)	0.0112 (17)	−0.0041 (17)
C29	0.080 (3)	0.058 (2)	0.087 (3)	0.006 (2)	0.012 (2)	−0.011 (2)
C30	0.076 (3)	0.080 (3)	0.090 (3)	−0.008 (2)	0.028 (2)	−0.037 (3)
C31	0.092 (3)	0.105 (4)	0.058 (2)	−0.016 (3)	0.031 (2)	−0.026 (3)
C32	0.082 (3)	0.066 (2)	0.049 (2)	−0.005 (2)	0.0206 (19)	−0.0041 (17)
C33	0.0408 (16)	0.0500 (18)	0.0513 (18)	0.0015 (14)	0.0135 (14)	0.0051 (15)
C34	0.049 (2)	0.099 (3)	0.054 (2)	0.0012 (19)	0.0168 (17)	0.007 (2)
C35	0.068 (3)	0.121 (4)	0.078 (3)	0.010 (3)	0.038 (2)	0.025 (3)
C36	0.057 (2)	0.085 (3)	0.115 (4)	−0.006 (2)	0.038 (3)	0.014 (3)
C37	0.054 (2)	0.075 (3)	0.107 (4)	−0.0156 (19)	0.023 (2)	−0.022 (3)
C38	0.054 (2)	0.065 (2)	0.072 (2)	−0.0098 (17)	0.0218 (18)	−0.0135 (19)
C39	0.0381 (15)	0.0523 (18)	0.0436 (17)	0.0000 (13)	0.0069 (13)	0.0058 (14)
C40	0.221 (5)	0.172 (5)	0.169 (4)	−0.058 (4)	0.052 (4)	−0.042 (4)
C41	0.213 (5)	0.174 (5)	0.176 (4)	−0.071 (4)	0.028 (5)	−0.032 (4)
C42	0.233 (6)	0.178 (5)	0.167 (5)	−0.041 (4)	0.029 (5)	−0.048 (4)

Geometric parameters (Å, º) top

Cu1—P3	2.2740 (8)	C18—H18	0.9300
Cu1—P1	2.2992 (8)	C19—C20	1.389 (6)
Cu1—P2	2.3205 (9)	C19—H19	0.9300
Cu1—Br1	2.4381 (5)	C20—H20	0.9300
P1—C7	1.818 (3)	C21—C26	1.374 (5)
P1—C1	1.824 (3)	C21—C22	1.388 (5)
P1—C13	1.845 (3)	C22—C23	1.412 (6)
P2—C15	1.824 (3)	C22—H22	0.9300
P2—C21	1.830 (3)	C23—C24	1.363 (8)
P2—C14	1.834 (3)	C23—H23	0.9300
P3—C27	1.823 (3)	C24—C25	1.352 (7)
P3—C33	1.838 (3)	C24—H24	0.9300
P3—C39	1.845 (3)	C25—C26	1.395 (6)
O1—C40	1.193 (11)	C25—H25	0.9300
C1—C6	1.373 (5)	C26—H26	0.9300
C1—C2	1.391 (5)	C27—C32	1.371 (5)
C2—C3	1.377 (5)	C27—C28	1.381 (5)
C2—H2	0.9300	C28—C29	1.366 (5)
C3—C4	1.367 (6)	C28—H28	0.9300
C3—H3	0.9300	C29—C30	1.362 (6)
C4—C5	1.372 (6)	C29—H29	0.9300
C4—H4	0.9300	C30—C31	1.354 (6)
C5—C6	1.395 (5)	C30—H30	0.9300
C5—H5	0.9300	C31—C32	1.395 (6)
C6—H6	0.9300	C31—H31	0.9300
C7—C8	1.369 (5)	C32—H32	0.9300
C7—C12	1.381 (5)	C33—C34	1.372 (5)
C8—C9	1.385 (6)	C33—C38	1.377 (5)
C8—H8	0.9300	C34—C35	1.396 (5)
C9—C10	1.362 (6)	C34—H34	0.9300
C9—H9	0.9300	C35—C36	1.352 (7)
C10—C11	1.349 (6)	C35—H35	0.9300
C10—H10	0.9300	C36—C37	1.351 (7)
C11—C12	1.387 (5)	C36—H36	0.9300
C11—H11	0.9300	C37—C38	1.387 (5)
C12—H12	0.9300	C37—H37	0.9300
C13—C14	1.537 (5)	C38—H38	0.9300
C13—H13A	0.9700	C39—C39ⁱ	1.533 (6)
C13—H13B	0.9700	C39—H39A	0.9700
C14—H14A	0.9700	C39—H39B	0.9700
C14—H14B	0.9700	C40—C41	1.417 (9)
C15—C16	1.379 (5)	C40—C42	1.422 (9)
C15—C20	1.385 (5)	C41—H41A	0.9600
C16—C17	1.394 (5)	C41—H41B	0.9600
C16—H16	0.9300	C41—H41C	0.9600
C17—C18	1.337 (6)	C42—H42A	0.9600
C17—H17	0.9300	C42—H42B	0.9600
C18—C19	1.368 (7)	C42—H42C	0.9600

P3—Cu1—P1	113.74 (3)	C19—C18—H18	120.3
P3—Cu1—P2	122.23 (3)	C18—C19—C20	121.2 (4)
P1—Cu1—P2	89.30 (3)	C18—C19—H19	119.4
P3—Cu1—Br1	102.02 (3)	C20—C19—H19	119.4
P1—Cu1—Br1	115.56 (3)	C15—C20—C19	119.4 (4)
P2—Cu1—Br1	114.67 (3)	C15—C20—H20	120.3
C7—P1—C1	104.76 (14)	C19—C20—H20	120.3
C7—P1—C13	104.07 (15)	C26—C21—C22	118.8 (4)
C1—P1—C13	98.90 (15)	C26—C21—P2	124.6 (3)
C7—P1—Cu1	122.50 (10)	C22—C21—P2	116.6 (3)
C1—P1—Cu1	120.75 (11)	C21—C22—C23	119.0 (5)
C13—P1—Cu1	101.66 (10)	C21—C22—H22	120.5
C15—P2—C21	101.58 (15)	C23—C22—H22	120.5
C15—P2—C14	102.75 (14)	C24—C23—C22	120.6 (5)
C21—P2—C14	102.84 (16)	C24—C23—H23	119.7
C15—P2—Cu1	123.55 (11)	C22—C23—H23	119.7
C21—P2—Cu1	120.64 (11)	C25—C24—C23	120.5 (5)
C14—P2—Cu1	102.29 (10)	C25—C24—H24	119.8
C27—P3—C33	100.83 (15)	C23—C24—H24	119.8
C27—P3—C39	105.88 (15)	C24—C25—C26	119.7 (5)
C33—P3—C39	102.06 (14)	C24—C25—H25	120.1
C27—P3—Cu1	115.67 (11)	C26—C25—H25	120.1
C33—P3—Cu1	115.37 (11)	C21—C26—C25	121.4 (5)
C39—P3—Cu1	115.16 (10)	C21—C26—H26	119.3
C6—C1—C2	119.0 (3)	C25—C26—H26	119.3
C6—C1—P1	119.1 (3)	C32—C27—C28	117.5 (3)
C2—C1—P1	121.5 (3)	C32—C27—P3	124.7 (3)
C3—C2—C1	120.2 (4)	C28—C27—P3	117.8 (3)
C3—C2—H2	119.9	C29—C28—C27	122.1 (4)
C1—C2—H2	119.9	C29—C28—H28	119.0
C4—C3—C2	120.5 (4)	C27—C28—H28	119.0
C4—C3—H3	119.7	C30—C29—C28	119.7 (4)
C2—C3—H3	119.7	C30—C29—H29	120.2
C3—C4—C5	120.1 (4)	C28—C29—H29	120.2
C3—C4—H4	120.0	C31—C30—C29	119.8 (4)
C5—C4—H4	120.0	C31—C30—H30	120.1
C4—C5—C6	119.8 (4)	C29—C30—H30	120.1
C4—C5—H5	120.1	C30—C31—C32	120.7 (4)
C6—C5—H5	120.1	C30—C31—H31	119.7
C1—C6—C5	120.4 (4)	C32—C31—H31	119.7
C1—C6—H6	119.8	C27—C32—C31	120.2 (4)
C5—C6—H6	119.8	C27—C32—H32	119.9
C8—C7—C12	117.8 (3)	C31—C32—H32	119.9
C8—C7—P1	121.5 (3)	C34—C33—C38	118.7 (3)
C12—C7—P1	120.3 (3)	C34—C33—P3	119.7 (3)
C7—C8—C9	121.4 (4)	C38—C33—P3	121.7 (3)
C7—C8—H8	119.3	C33—C34—C35	119.8 (4)
C9—C8—H8	119.3	C33—C34—H34	120.1
C10—C9—C8	119.7 (4)	C35—C34—H34	120.1
C10—C9—H9	120.2	C36—C35—C34	120.4 (4)
C8—C9—H9	120.2	C36—C35—H35	119.8
C11—C10—C9	120.1 (4)	C34—C35—H35	119.8
C11—C10—H10	119.9	C37—C36—C35	120.6 (4)
C9—C10—H10	119.9	C37—C36—H36	119.7
C10—C11—C12	120.3 (4)	C35—C36—H36	119.7
C10—C11—H11	119.8	C36—C37—C38	119.7 (4)
C12—C11—H11	119.8	C36—C37—H37	120.1
C7—C12—C11	120.6 (4)	C38—C37—H37	120.1
C7—C12—H12	119.7	C33—C38—C37	120.8 (4)
C11—C12—H12	119.7	C33—C38—H38	119.6
C14—C13—P1	108.1 (2)	C37—C38—H38	119.6
C14—C13—H13A	110.1	C39ⁱ—C39—P3	114.0 (3)
P1—C13—H13A	110.1	C39ⁱ—C39—H39A	108.7
C14—C13—H13B	110.1	P3—C39—H39A	108.7
P1—C13—H13B	110.1	C39ⁱ—C39—H39B	108.7
H13A—C13—H13B	108.4	P3—C39—H39B	108.7
C13—C14—P2	110.4 (2)	H39A—C39—H39B	107.6
C13—C14—H14A	109.6	O1—C40—C41	125.0 (10)
P2—C14—H14A	109.6	O1—C40—C42	117.3 (10)
C13—C14—H14B	109.6	C41—C40—C42	115.1 (11)
P2—C14—H14B	109.6	C40—C41—H41A	109.5
H14A—C14—H14B	108.1	C40—C41—H41B	109.5
C16—C15—C20	118.8 (3)	H41A—C41—H41B	109.5
C16—C15—P2	119.1 (3)	C40—C41—H41C	109.5
C20—C15—P2	122.1 (3)	H41A—C41—H41C	109.5
C15—C16—C17	120.0 (4)	H41B—C41—H41C	109.5
C15—C16—H16	120.0	C40—C42—H42A	109.5
C17—C16—H16	120.0	C40—C42—H42B	109.5
C18—C17—C16	121.2 (4)	H42A—C42—H42B	109.5
C18—C17—H17	119.4	C40—C42—H42C	109.5
C16—C17—H17	119.4	H42A—C42—H42C	109.5
C17—C18—C19	119.4 (4)	H42B—C42—H42C	109.5
C17—C18—H18	120.3

P3—Cu1—P1—C7	−8.49 (14)	Cu1—P2—C14—C13	39.9 (2)
P2—Cu1—P1—C7	−133.75 (13)	C21—P2—C15—C16	136.2 (3)
Br1—Cu1—P1—C7	109.07 (13)	C14—P2—C15—C16	−117.6 (3)
P3—Cu1—P1—C1	−145.43 (12)	Cu1—P2—C15—C16	−3.3 (3)
P2—Cu1—P1—C1	89.31 (12)	C21—P2—C15—C20	−43.9 (3)
Br1—Cu1—P1—C1	−27.88 (12)	C14—P2—C15—C20	62.3 (3)
P3—Cu1—P1—C13	106.71 (12)	Cu1—P2—C15—C20	176.7 (2)
P2—Cu1—P1—C13	−18.55 (12)	C20—C15—C16—C17	0.2 (5)
Br1—Cu1—P1—C13	−135.73 (12)	P2—C15—C16—C17	−179.9 (3)
P3—Cu1—P2—C15	119.84 (12)	C15—C16—C17—C18	−0.5 (6)
P1—Cu1—P2—C15	−122.24 (12)	C16—C17—C18—C19	0.5 (7)
Br1—Cu1—P2—C15	−4.25 (12)	C17—C18—C19—C20	−0.3 (7)
P3—Cu1—P2—C21	−12.44 (15)	C16—C15—C20—C19	0.1 (5)
P1—Cu1—P2—C21	105.48 (14)	P2—C15—C20—C19	−179.9 (3)
Br1—Cu1—P2—C21	−136.53 (14)	C18—C19—C20—C15	0.0 (6)
P3—Cu1—P2—C14	−125.61 (11)	C15—P2—C21—C26	114.5 (3)
P1—Cu1—P2—C14	−7.68 (11)	C14—P2—C21—C26	8.4 (3)
Br1—Cu1—P2—C14	110.30 (11)	Cu1—P2—C21—C26	−104.5 (3)
P1—Cu1—P3—C27	−43.39 (12)	C15—P2—C21—C22	−66.6 (3)
P2—Cu1—P3—C27	61.77 (13)	C14—P2—C21—C22	−172.8 (3)
Br1—Cu1—P3—C27	−168.53 (12)	Cu1—P2—C21—C22	74.3 (3)
P1—Cu1—P3—C33	−160.69 (12)	C26—C21—C22—C23	−0.2 (5)
P2—Cu1—P3—C33	−55.52 (12)	P2—C21—C22—C23	−179.1 (3)
Br1—Cu1—P3—C33	74.17 (12)	C21—C22—C23—C24	−0.1 (7)
P1—Cu1—P3—C39	80.75 (12)	C22—C23—C24—C25	0.8 (8)
P2—Cu1—P3—C39	−174.08 (11)	C23—C24—C25—C26	−1.2 (8)
Br1—Cu1—P3—C39	−44.39 (12)	C22—C21—C26—C25	−0.2 (6)
C7—P1—C1—C6	−147.2 (3)	P2—C21—C26—C25	178.6 (3)
C13—P1—C1—C6	105.6 (3)	C24—C25—C26—C21	0.9 (7)
Cu1—P1—C1—C6	−3.7 (3)	C33—P3—C27—C32	−109.5 (3)
C7—P1—C1—C2	40.1 (3)	C39—P3—C27—C32	−3.5 (3)
C13—P1—C1—C2	−67.1 (3)	Cu1—P3—C27—C32	125.4 (3)
Cu1—P1—C1—C2	−176.4 (2)	C33—P3—C27—C28	71.9 (3)
C6—C1—C2—C3	−0.8 (5)	C39—P3—C27—C28	177.9 (3)
P1—C1—C2—C3	171.9 (3)	Cu1—P3—C27—C28	−53.3 (3)
C1—C2—C3—C4	−0.3 (6)	C32—C27—C28—C29	−0.1 (5)
C2—C3—C4—C5	0.9 (7)	P3—C27—C28—C29	178.6 (3)
C3—C4—C5—C6	−0.5 (7)	C27—C28—C29—C30	−1.0 (6)
C2—C1—C6—C5	1.2 (5)	C28—C29—C30—C31	1.5 (7)
P1—C1—C6—C5	−171.7 (3)	C29—C30—C31—C32	−0.9 (7)
C4—C5—C6—C1	−0.6 (6)	C28—C27—C32—C31	0.7 (5)
C1—P1—C7—C8	−141.9 (3)	P3—C27—C32—C31	−177.9 (3)
C13—P1—C7—C8	−38.5 (3)	C30—C31—C32—C27	−0.2 (7)
Cu1—P1—C7—C8	75.5 (3)	C27—P3—C33—C34	−137.3 (3)
C1—P1—C7—C12	45.7 (3)	C39—P3—C33—C34	113.6 (3)
C13—P1—C7—C12	149.0 (3)	Cu1—P3—C33—C34	−12.0 (3)
Cu1—P1—C7—C12	−97.0 (3)	C27—P3—C33—C38	40.8 (3)
C12—C7—C8—C9	−1.2 (6)	C39—P3—C33—C38	−68.2 (3)
P1—C7—C8—C9	−173.8 (4)	Cu1—P3—C33—C38	166.2 (3)
C7—C8—C9—C10	0.5 (8)	C38—C33—C34—C35	−0.5 (6)
C8—C9—C10—C11	0.9 (8)	P3—C33—C34—C35	177.7 (3)
C9—C10—C11—C12	−1.5 (7)	C33—C34—C35—C36	0.7 (7)
C8—C7—C12—C11	0.6 (5)	C34—C35—C36—C37	0.1 (8)
P1—C7—C12—C11	173.3 (3)	C35—C36—C37—C38	−1.0 (7)
C10—C11—C12—C7	0.8 (6)	C34—C33—C38—C37	−0.4 (6)
C7—P1—C13—C14	176.0 (2)	P3—C33—C38—C37	−178.5 (3)
C1—P1—C13—C14	−76.3 (2)	C36—C37—C38—C33	1.2 (7)
Cu1—P1—C13—C14	47.8 (2)	C27—P3—C39—C39ⁱ	80.6 (3)
P1—C13—C14—P2	−59.6 (3)	C33—P3—C39—C39ⁱ	−174.3 (3)
C15—P2—C14—C13	168.9 (2)	Cu1—P3—C39—C39ⁱ	−48.5 (4)
C21—P2—C14—C13	−85.9 (2)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16···Br1	0.93	2.86	3.760 (4)	164
C32—H32···Br1ⁱ	0.93	2.82	3.666 (4)	151

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	[Cu₂Br₂(C₂₆H₂₄P₂)₃]·2C₃H₆O
M_r	1598.23
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	295
a, b, c (Å)	12.5301 (6), 21.8966 (10), 14.8028 (7)
β (°)	105.932 (1)
V (Å³)	3905.4 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.74
Crystal size (mm)	0.20 × 0.18 × 0.17

Data collection
Diffractometer	Bruker SMART APEX area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.691, 0.752
No. of measured, independent and observed [I > 2σ(I)] reflections	33389, 8907, 6429
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.129, 1.02
No. of reflections	8907
No. of parameters	435
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.75, −0.42

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top

Cu1—P3	2.2740 (8)	Cu1—P2	2.3205 (9)
Cu1—P1	2.2992 (8)	Cu1—Br1	2.4381 (5)

P3—Cu1—P1	113.74 (3)	P3—Cu1—Br1	102.02 (3)
P3—Cu1—P2	122.23 (3)	P1—Cu1—Br1	115.56 (3)
P1—Cu1—P2	89.30 (3)	P2—Cu1—Br1	114.67 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16···Br1	0.93	2.86	3.760 (4)	163.5
C32—H32···Br1ⁱ	0.93	2.82	3.666 (4)	151.2

Symmetry code: (i) −x+1, −y+1, −z+1.

Acknowledgements

The author thanks Jiangxi Science and Technology Normal University for supporting this study.

References

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ISSN: 2056-9890

Volume 64| Part 10| October 2008| Pages m1346-m1347

doi:10.1107/S1600536808031000

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