Iodido[5-methyl-1H-benzimidazole-2(3H)-thione-κS]bis­(triphenyl­phosphane-κP)copper(I) methanol monosolvate

Jiang, Y.-H.; Qiu, Q.-M.; Jiang, R.-X.; Huang, X.; Jin, Q.-H.

doi:10.1107/S1600536812039165

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 10| October 2012| Page m1295

https://doi.org/10.1107/S1600536812039165

Open

access

Iodido[5-methyl-1H-benzimidazole-2(3H)-thione-κS]bis(triphenylphosphane-κP)copper(I) methanol monosolvate

Yu-Han Jiang,^a Qi-Ming Qiu,^a Rui-Xia Jiang,^b Xu Huang ^a and Qiong-Hua Jin ^a ^*

^aDepartment of Chemistry, Capital Normal University, Beijing 100048, People's Republic of China, and ^bQingdao Hygain Chemical (Group) Co. Ltd, Qingdao 266044, People's Republic of China
^*Correspondence e-mail: jinqh204@163.com

(Received 2 September 2012; accepted 13 September 2012; online 26 September 2012)

In the title compound, [CuI(C₈H₈N₂S)(C₁₈H₁₅P)₂]·CH₃OH, the coordination environment around the Cu^I atom is distorted tetrahedral, defined by two P atoms of two triphenylphosphane ligands, one S atom of a 5-methyl-1H-benzimidazole-2(3H)-thione ligand and one I atom. The complex molecules and the methanol solvent molecules are connected via N—H⋯O and O—H⋯I hydrogen bonds, forming a chain along [010]. An intramolecular N—H⋯I hydrogen bond is also observed.

Related literature

For the structures and properties of transition metal complexes with phosphanes, see: Baxter et al. (1994 ); Kitagawa et al. (1995 ); Lewis et al. (1996 ). For complexes with a 2-mercapto-5-methylbenzimidazole ligand, see: Ozturk et al. (2009 ); Schneider et al. (2008 ). For related structures, see: Aslanidis et al. (1993 ); Li et al. (2004 ); Lobana et al. (2005 ).

Experimental

Crystal data

[CuI(C₈H₈N₂S)(C₁₈H₁₅P)₂]·CH₄O
M_r = 911.27
Monoclinic, P 2₁ /c
a = 15.6081 (11) Å
b = 10.5938 (8) Å
c = 25.976 (2) Å
β = 96.919 (1)°
V = 4263.8 (5) Å³
Z = 4
Mo Kα radiation
μ = 1.40 mm⁻¹
T = 298 K
0.43 × 0.38 × 0.35 mm

Data collection

Bruker APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.585, T_max = 0.641
20808 measured reflections
7504 independent reflections
5465 reflections with I > 2σ(I)
R_int = 0.037

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.088
S = 1.09
7504 reflections
478 parameters
H-atom parameters constrained
Δρ_max = 0.75 e Å⁻³
Δρ_min = −0.54 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.86	1.97	2.755 (7)	152
N2—H2⋯I1	0.86	2.80	3.539 (3)	145
O1—H1A⋯I1	0.82	2.67	3.469 (5)	164
Symmetry code: (i) x, y+1, z.

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT-Plus (Bruker, 2007); data reduction: SAINT-Plus; 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 global, I. DOI: https://doi.org/10.1107/S1600536812039165/hy2586sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812039165/hy2586Isup2.hkl

checkCIF report

Comment top

Various transition metal complexes with bridging phosphanes or functionalized phosphanes have drawn much attention in recent years for their special structures, novel reactivity performances, catalytic properties and luminescence (Baxter et al., 1994; Kitagawa et al., 1995; Lewis et al., 1996). The 2-mercapto-5-methylbenzimidazole (MMBI) ligand, with an -SH group and two potential coordination N atoms, is excellent in building supramolecular structures (Ozturk et al., 2009; Schneider et al., 2008). However, to our best knowledge, Cu(I) complexes with the MMBI ligand have not been reported. In this paper, one Cu(I) complex with PPh₃ and MMBI is reported.

In the title compound, MMBI acts as a neutral, monodentate ligand with the S atom as a coordination atom. Other sites of the coordination tetrahedron are occupied by two P atoms from two PPh₃ ligands and an iodide anion (Fig. 1). The Cu—S, Cu—P and Cu—I bond lengths agree with those in [CuI(H₂itsc)(Ph₃P)₂] (H₂itsc = isatin-3-thiosemicarbazones) (Lobana et al., 2005) and [CuI(C₄H₆N₂S)(C₁₈H₁₅P)₂] (Li et al., 2004). Similarly, in the title complex, angles around the Cu atom ranging from 102.31 (4) to 122.72 (4)° are close to those in [CuI(PPh₃)₂(pymtH)] (pymtH = pyrimidine-2-thione) (Aslanidis et al., 1993). The complex molecules and the solvent methanol molecules are connected via N—H···O and O—H···I hydrogen bonds (Table 1), forming a chain along [0 1 0]. An intramolecular N—H···I hydrogen bond is also observed.

Related literature top

For the structures and properties of transition metal complexes with phosphanes, see: Baxter et al. (1994); Kitagawa et al. (1995); Lewis et al. (1996). For complexes with a 2-mercapto-5-methylbenzimidazole ligand, see: Ozturk et al. (2009); Schneider et al. (2008). For related structures, see: Aslanidis et al. (1993); Li et al. (2004); Lobana et al. (2005).

Experimental top

A mixture of CuI (0.2 mmol) and 2-mercapto-5-methylbenzimidazole (0.2 mmol) in MeOH and CH₂Cl₂ (10 ml, v/v = 1:1) was stirred for 2 h. PPh₃ (0.2 mmol) was added to the mixture, which was stirred for another 4 h. The insoluble residues were removed by filtration, and filtrate was evaporated slowly at room temperature for a week to yield colorless crystalline products.

Structure description top

For the structures and properties of transition metal complexes with phosphanes, see: Baxter et al. (1994); Kitagawa et al. (1995); Lewis et al. (1996). For complexes with a 2-mercapto-5-methylbenzimidazole ligand, see: Ozturk et al. (2009); Schneider et al. (2008). For related structures, see: Aslanidis et al. (1993); Li et al. (2004); Lobana et al. (2005).

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT-Plus (Bruker, 2007); data reduction: SAINT-Plus (Bruker, 2007); 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 the title compound. Displacement ellipsoids are drawn at the 50% probability level. H atoms have been omitted for clarity.

Iodido[5-methyl-1H-benzimidazole-2(3H)-thione- κS]bis(triphenylphosphane-κP)copper(I) methanol monosolvate top

Crystal data top

[CuI(C₈H₈N₂S)(C₁₈H₁₅P)₂]·CH₄O	F(000) = 1848
M_r = 911.27	D_x = 1.420 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8084 reflections
a = 15.6081 (11) Å	θ = 2.3–26.4°
b = 10.5938 (8) Å	µ = 1.40 mm⁻¹
c = 25.976 (2) Å	T = 298 K
β = 96.919 (1)°	Block, colorless
V = 4263.8 (5) Å³	0.43 × 0.38 × 0.35 mm
Z = 4

Data collection top

Bruker APEX CCD diffractometer	7504 independent reflections
Radiation source: fine-focus sealed tube	5465 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.037
φ and ω scans	θ_max = 25.0°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −18→17
T_min = 0.585, T_max = 0.641	k = −12→11
20808 measured reflections	l = −24→30

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.088	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0172P)² + 5.6518P] where P = (F_o² + 2F_c²)/3
7504 reflections	(Δ/σ)_max = 0.001
478 parameters	Δρ_max = 0.75 e Å⁻³
0 restraints	Δρ_min = −0.54 e Å⁻³

Crystal data top

[CuI(C₈H₈N₂S)(C₁₈H₁₅P)₂]·CH₄O	V = 4263.8 (5) Å³
M_r = 911.27	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 15.6081 (11) Å	µ = 1.40 mm⁻¹
b = 10.5938 (8) Å	T = 298 K
c = 25.976 (2) Å	0.43 × 0.38 × 0.35 mm
β = 96.919 (1)°

Data collection top

Bruker APEX CCD diffractometer	7504 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	5465 reflections with I > 2σ(I)
T_min = 0.585, T_max = 0.641	R_int = 0.037
20808 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.088	H-atom parameters constrained
S = 1.09	Δρ_max = 0.75 e Å⁻³
7504 reflections	Δρ_min = −0.54 e Å⁻³
478 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	0.29356 (3)	0.60884 (4)	0.391446 (18)	0.03756 (13)
I1	0.426976 (18)	0.44881 (3)	0.414919 (13)	0.05740 (11)
N1	0.4673 (2)	0.9549 (3)	0.43122 (14)	0.0537 (9)
H1	0.4405	1.0245	0.4233	0.064*
N2	0.4928 (2)	0.7598 (3)	0.45022 (14)	0.0538 (10)
H2	0.4850	0.6814	0.4569	0.065*
O1	0.3820 (4)	0.1429 (4)	0.3723 (3)	0.134 (2)
H1A	0.4018	0.2133	0.3794	0.201*
P1	0.18454 (6)	0.53857 (10)	0.43498 (4)	0.0349 (2)
P2	0.27571 (7)	0.64671 (10)	0.30391 (4)	0.0392 (3)
S1	0.32156 (7)	0.81432 (10)	0.42639 (5)	0.0535 (3)
C1	0.4289 (3)	0.8418 (4)	0.43596 (15)	0.0453 (10)
C2	0.5732 (3)	0.8173 (4)	0.45291 (16)	0.0499 (11)
C3	0.5561 (3)	0.9423 (4)	0.44091 (16)	0.0481 (10)
C4	0.6229 (3)	1.0295 (4)	0.44001 (19)	0.0647 (14)
H4	0.6114	1.1140	0.4323	0.078*
C5	0.7071 (3)	0.9861 (5)	0.4510 (2)	0.0641 (14)
C6	0.7220 (3)	0.8599 (5)	0.46243 (19)	0.0668 (14)
H6	0.7786	0.8322	0.4698	0.080*
C7	0.6563 (3)	0.7739 (5)	0.46341 (19)	0.0663 (14)
H7	0.6678	0.6892	0.4709	0.080*
C8	0.7824 (3)	1.0764 (5)	0.4514 (3)	0.100 (2)
H8A	0.8228	1.0612	0.4817	0.151*
H8B	0.7618	1.1617	0.4521	0.151*
H8C	0.8103	1.0636	0.4209	0.151*
C9	0.1375 (3)	0.3813 (4)	0.42121 (15)	0.0431 (10)
C10	0.1941 (3)	0.2831 (4)	0.41679 (17)	0.0565 (12)
H10	0.2530	0.2991	0.4187	0.068*
C11	0.1638 (4)	0.1607 (5)	0.4095 (2)	0.0775 (16)
H11	0.2026	0.0946	0.4075	0.093*
C12	0.0777 (5)	0.1367 (6)	0.4053 (2)	0.0850 (19)
H12	0.0577	0.0545	0.3999	0.102*
C13	0.0205 (4)	0.2325 (6)	0.4090 (2)	0.0826 (18)
H13	−0.0384	0.2154	0.4062	0.099*
C14	0.0498 (3)	0.3555 (5)	0.41675 (17)	0.0596 (13)
H14	0.0106	0.4208	0.4190	0.072*
C15	0.0922 (2)	0.6456 (4)	0.42431 (15)	0.0376 (9)
C16	0.0621 (3)	0.7184 (4)	0.46264 (17)	0.0478 (11)
H16	0.0869	0.7103	0.4969	0.057*
C17	−0.0048 (3)	0.8032 (4)	0.4501 (2)	0.0631 (13)
H17	−0.0248	0.8515	0.4760	0.076*
C18	−0.0417 (3)	0.8166 (5)	0.3999 (2)	0.0678 (15)
H18	−0.0863	0.8741	0.3918	0.081*
C19	−0.0132 (3)	0.7459 (5)	0.3618 (2)	0.0672 (15)
H19	−0.0388	0.7545	0.3277	0.081*
C20	0.0537 (3)	0.6610 (5)	0.37340 (18)	0.0578 (12)
H20	0.0732	0.6137	0.3470	0.069*
C21	0.2100 (2)	0.5320 (3)	0.50569 (14)	0.0357 (9)
C22	0.1545 (3)	0.4788 (4)	0.53712 (16)	0.0530 (12)
H22	0.1025	0.4445	0.5223	0.064*
C23	0.1752 (3)	0.4759 (5)	0.59040 (18)	0.0652 (14)
H23	0.1369	0.4409	0.6112	0.078*
C24	0.2523 (3)	0.5247 (5)	0.61249 (17)	0.0637 (13)
H24	0.2663	0.5231	0.6483	0.076*
C25	0.3087 (3)	0.5759 (5)	0.58182 (17)	0.0614 (13)
H25	0.3615	0.6076	0.5968	0.074*
C26	0.2874 (3)	0.5804 (4)	0.52853 (16)	0.0468 (11)
H26	0.3256	0.6164	0.5079	0.056*
C27	0.2603 (2)	0.5071 (4)	0.26301 (15)	0.0449 (10)
C28	0.2276 (3)	0.4022 (5)	0.2840 (2)	0.0696 (14)
H28	0.2157	0.4035	0.3182	0.083*
C29	0.2119 (4)	0.2933 (6)	0.2545 (3)	0.098 (2)
H29	0.1882	0.2230	0.2688	0.117*
C30	0.2309 (4)	0.2887 (7)	0.2047 (3)	0.094 (2)
H30	0.2210	0.2154	0.1853	0.113*
C31	0.2642 (4)	0.3912 (7)	0.1840 (2)	0.0859 (19)
H31	0.2773	0.3882	0.1500	0.103*
C32	0.2792 (3)	0.5009 (5)	0.21231 (18)	0.0669 (14)
H32	0.3022	0.5710	0.1973	0.080*
C33	0.3667 (3)	0.7297 (4)	0.28087 (16)	0.0481 (11)
C34	0.4472 (3)	0.7145 (5)	0.30815 (18)	0.0585 (13)
H34	0.4540	0.6615	0.3369	0.070*
C35	0.5177 (3)	0.7767 (6)	0.2934 (2)	0.0873 (19)
H35	0.5714	0.7668	0.3127	0.105*
C36	0.5095 (4)	0.8528 (6)	0.2506 (2)	0.093 (2)
H36	0.5576	0.8928	0.2403	0.111*
C37	0.4308 (4)	0.8694 (6)	0.2234 (2)	0.101 (2)
H37	0.4248	0.9223	0.1946	0.122*
C38	0.3591 (3)	0.8083 (6)	0.2381 (2)	0.0815 (18)
H38	0.3054	0.8203	0.2190	0.098*
C39	0.1847 (3)	0.7474 (4)	0.27877 (15)	0.0443 (10)
C40	0.1187 (3)	0.7103 (5)	0.24166 (18)	0.0624 (13)
H40	0.1197	0.6300	0.2273	0.075*
C41	0.0506 (3)	0.7915 (6)	0.2253 (2)	0.0832 (17)
H41	0.0064	0.7650	0.2005	0.100*
C42	0.0491 (4)	0.9100 (6)	0.2459 (2)	0.0891 (19)
H42	0.0045	0.9651	0.2342	0.107*
C43	0.1126 (4)	0.9482 (5)	0.2836 (2)	0.0821 (16)
H43	0.1105	1.0283	0.2981	0.099*
C44	0.1801 (3)	0.8674 (5)	0.3002 (2)	0.0683 (14)
H44	0.2229	0.8936	0.3261	0.082*
C45	0.3990 (8)	0.1101 (10)	0.3249 (4)	0.204 (5)
H45A	0.4585	0.1275	0.3217	0.306*
H45B	0.3628	0.1576	0.2994	0.306*
H45C	0.3880	0.0216	0.3197	0.306*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0345 (3)	0.0433 (3)	0.0356 (3)	−0.0078 (2)	0.0072 (2)	−0.0013 (2)
I1	0.04338 (17)	0.04799 (18)	0.0800 (2)	−0.00010 (14)	0.00389 (15)	0.00189 (16)
N1	0.063 (2)	0.034 (2)	0.064 (2)	−0.0099 (18)	0.0073 (19)	−0.0053 (17)
N2	0.055 (2)	0.043 (2)	0.061 (2)	−0.0163 (19)	−0.0026 (19)	0.0114 (18)
O1	0.152 (5)	0.051 (3)	0.198 (6)	0.022 (3)	0.022 (5)	0.008 (3)
P1	0.0314 (5)	0.0405 (6)	0.0333 (6)	−0.0095 (4)	0.0057 (4)	−0.0015 (4)
P2	0.0362 (6)	0.0484 (6)	0.0332 (6)	−0.0073 (5)	0.0047 (5)	0.0012 (5)
S1	0.0521 (7)	0.0440 (6)	0.0647 (8)	−0.0101 (5)	0.0080 (6)	−0.0121 (5)
C1	0.055 (3)	0.042 (2)	0.039 (2)	−0.013 (2)	0.005 (2)	−0.0073 (19)
C2	0.057 (3)	0.046 (3)	0.043 (3)	−0.017 (2)	−0.004 (2)	0.001 (2)
C3	0.050 (3)	0.047 (3)	0.048 (3)	−0.011 (2)	0.008 (2)	−0.011 (2)
C4	0.076 (4)	0.037 (3)	0.083 (4)	−0.017 (2)	0.019 (3)	−0.013 (2)
C5	0.054 (3)	0.065 (3)	0.075 (4)	−0.018 (3)	0.015 (3)	−0.025 (3)
C6	0.056 (3)	0.070 (4)	0.073 (4)	−0.008 (3)	0.001 (3)	−0.009 (3)
C7	0.062 (3)	0.058 (3)	0.076 (4)	−0.008 (3)	−0.004 (3)	0.009 (3)
C8	0.069 (4)	0.076 (4)	0.161 (6)	−0.029 (3)	0.035 (4)	−0.045 (4)
C9	0.048 (3)	0.046 (3)	0.036 (2)	−0.018 (2)	0.0087 (19)	−0.0029 (19)
C10	0.061 (3)	0.048 (3)	0.060 (3)	−0.013 (2)	0.007 (2)	−0.002 (2)
C11	0.110 (5)	0.045 (3)	0.077 (4)	−0.008 (3)	0.011 (3)	−0.003 (3)
C12	0.128 (6)	0.067 (4)	0.062 (4)	−0.054 (4)	0.021 (4)	−0.011 (3)
C13	0.083 (4)	0.100 (5)	0.067 (4)	−0.058 (4)	0.020 (3)	−0.017 (3)
C14	0.050 (3)	0.071 (3)	0.059 (3)	−0.028 (2)	0.012 (2)	−0.010 (2)
C15	0.031 (2)	0.045 (2)	0.037 (2)	−0.0108 (17)	0.0059 (18)	0.0059 (18)
C16	0.042 (2)	0.054 (3)	0.046 (3)	−0.003 (2)	0.001 (2)	−0.003 (2)
C17	0.054 (3)	0.053 (3)	0.083 (4)	0.004 (2)	0.009 (3)	−0.004 (3)
C18	0.043 (3)	0.065 (3)	0.094 (4)	0.009 (2)	0.002 (3)	0.026 (3)
C19	0.044 (3)	0.097 (4)	0.059 (3)	0.002 (3)	−0.002 (2)	0.032 (3)
C20	0.039 (3)	0.086 (4)	0.049 (3)	−0.004 (2)	0.009 (2)	0.008 (2)
C21	0.034 (2)	0.035 (2)	0.038 (2)	−0.0019 (17)	0.0062 (17)	−0.0004 (17)
C22	0.046 (3)	0.073 (3)	0.040 (3)	−0.015 (2)	0.004 (2)	0.008 (2)
C23	0.062 (3)	0.089 (4)	0.046 (3)	−0.019 (3)	0.013 (2)	0.017 (3)
C24	0.076 (4)	0.079 (4)	0.035 (3)	−0.015 (3)	−0.001 (2)	0.008 (2)
C25	0.054 (3)	0.080 (4)	0.047 (3)	−0.018 (3)	−0.008 (2)	0.003 (2)
C26	0.045 (2)	0.056 (3)	0.039 (2)	−0.012 (2)	0.0033 (19)	0.003 (2)
C27	0.034 (2)	0.063 (3)	0.036 (2)	0.000 (2)	−0.0015 (18)	−0.006 (2)
C28	0.081 (4)	0.062 (3)	0.067 (3)	−0.020 (3)	0.016 (3)	−0.022 (3)
C29	0.106 (5)	0.074 (4)	0.112 (6)	−0.025 (4)	0.008 (4)	−0.032 (4)
C30	0.074 (4)	0.100 (5)	0.101 (6)	0.014 (4)	−0.021 (4)	−0.063 (4)
C31	0.074 (4)	0.123 (6)	0.057 (4)	0.024 (4)	−0.006 (3)	−0.037 (4)
C32	0.068 (3)	0.091 (4)	0.042 (3)	0.009 (3)	0.009 (2)	−0.007 (3)
C33	0.041 (3)	0.063 (3)	0.041 (3)	−0.011 (2)	0.007 (2)	0.005 (2)
C34	0.043 (3)	0.077 (3)	0.056 (3)	−0.011 (2)	0.010 (2)	0.015 (2)
C35	0.041 (3)	0.138 (6)	0.084 (4)	−0.023 (3)	0.010 (3)	0.029 (4)
C36	0.058 (4)	0.133 (6)	0.090 (4)	−0.038 (4)	0.021 (3)	0.029 (4)
C37	0.079 (4)	0.144 (6)	0.080 (4)	−0.045 (4)	0.009 (3)	0.051 (4)
C38	0.056 (3)	0.118 (5)	0.068 (4)	−0.024 (3)	−0.002 (3)	0.041 (3)
C39	0.040 (2)	0.054 (3)	0.039 (2)	−0.006 (2)	0.0040 (19)	0.005 (2)
C40	0.057 (3)	0.076 (3)	0.052 (3)	0.005 (3)	−0.003 (2)	−0.004 (3)
C41	0.064 (4)	0.118 (5)	0.061 (4)	0.022 (4)	−0.017 (3)	−0.001 (3)
C42	0.086 (4)	0.099 (5)	0.081 (4)	0.037 (4)	0.000 (3)	0.029 (4)
C43	0.089 (4)	0.056 (3)	0.099 (5)	0.011 (3)	0.001 (4)	0.011 (3)
C44	0.067 (3)	0.054 (3)	0.081 (4)	0.000 (3)	−0.007 (3)	0.003 (3)
C45	0.287 (15)	0.139 (9)	0.187 (12)	0.045 (9)	0.035 (11)	0.054 (8)

Geometric parameters (Å, º) top

Cu1—P1	2.2786 (10)	C19—C20	1.383 (6)
Cu1—P2	2.2925 (11)	C19—H19	0.9300
Cu1—S1	2.3786 (12)	C20—H20	0.9300
Cu1—I1	2.6974 (6)	C21—C26	1.379 (5)
N1—C1	1.352 (5)	C21—C22	1.380 (5)
N1—C3	1.386 (5)	C22—C23	1.383 (6)
N1—H1	0.8600	C22—H22	0.9300
N2—C1	1.341 (5)	C23—C24	1.370 (6)
N2—C2	1.389 (5)	C23—H23	0.9300
N2—H2	0.8600	C24—C25	1.368 (6)
O1—C45	1.334 (10)	C24—H24	0.9300
O1—H1A	0.8200	C25—C26	1.385 (6)
P1—C15	1.829 (4)	C25—H25	0.9300
P1—C21	1.833 (4)	C26—H26	0.9300
P1—C9	1.839 (4)	C27—C28	1.363 (6)
P2—C27	1.820 (4)	C27—C32	1.386 (6)
P2—C33	1.831 (4)	C28—C29	1.390 (7)
P2—C39	1.833 (4)	C28—H28	0.9300
S1—C1	1.689 (4)	C29—C30	1.361 (8)
C2—C7	1.373 (6)	C29—H29	0.9300
C2—C3	1.378 (6)	C30—C31	1.344 (8)
C3—C4	1.395 (6)	C30—H30	0.9300
C4—C5	1.389 (7)	C31—C32	1.380 (7)
C4—H4	0.9300	C31—H31	0.9300
C5—C6	1.383 (7)	C32—H32	0.9300
C5—C8	1.514 (6)	C33—C34	1.376 (6)
C6—C7	1.374 (6)	C33—C38	1.382 (6)
C6—H6	0.9300	C34—C35	1.376 (6)
C7—H7	0.9300	C34—H34	0.9300
C8—H8A	0.9600	C35—C36	1.367 (7)
C8—H8B	0.9600	C35—H35	0.9300
C8—H8C	0.9600	C36—C37	1.352 (7)
C9—C10	1.378 (6)	C36—H36	0.9300
C9—C14	1.387 (6)	C37—C38	1.385 (6)
C10—C11	1.385 (6)	C37—H37	0.9300
C10—H10	0.9300	C38—H38	0.9300
C11—C12	1.360 (8)	C39—C40	1.380 (6)
C11—H11	0.9300	C39—C44	1.393 (6)
C12—C13	1.362 (8)	C40—C41	1.392 (7)
C12—H12	0.9300	C40—H40	0.9300
C13—C14	1.389 (7)	C41—C42	1.367 (8)
C13—H13	0.9300	C41—H41	0.9300
C14—H14	0.9300	C42—C43	1.369 (8)
C15—C16	1.385 (5)	C42—H42	0.9300
C15—C20	1.394 (5)	C43—C44	1.384 (7)
C16—C17	1.387 (6)	C43—H43	0.9300
C16—H16	0.9300	C44—H44	0.9300
C17—C18	1.368 (7)	C45—H45A	0.9600
C17—H17	0.9300	C45—H45B	0.9600
C18—C19	1.358 (7)	C45—H45C	0.9600
C18—H18	0.9300

P1—Cu1—P2	122.72 (4)	C18—C19—H19	119.9
P1—Cu1—S1	102.91 (4)	C20—C19—H19	119.9
P2—Cu1—S1	102.31 (4)	C19—C20—C15	120.7 (5)
P1—Cu1—I1	106.54 (3)	C19—C20—H20	119.7
P2—Cu1—I1	109.42 (3)	C15—C20—H20	119.7
S1—Cu1—I1	112.81 (3)	C26—C21—C22	118.5 (4)
C1—N1—C3	110.1 (4)	C26—C21—P1	119.3 (3)
C1—N1—H1	125.0	C22—C21—P1	122.2 (3)
C3—N1—H1	125.0	C21—C22—C23	120.9 (4)
C1—N2—C2	111.5 (3)	C21—C22—H22	119.6
C1—N2—H2	124.2	C23—C22—H22	119.6
C2—N2—H2	124.2	C24—C23—C22	119.9 (4)
C45—O1—H1A	109.5	C24—C23—H23	120.1
C15—P1—C21	104.32 (17)	C22—C23—H23	120.1
C15—P1—C9	104.08 (18)	C25—C24—C23	120.0 (4)
C21—P1—C9	101.16 (17)	C25—C24—H24	120.0
C15—P1—Cu1	110.15 (12)	C23—C24—H24	120.0
C21—P1—Cu1	115.16 (12)	C24—C25—C26	120.1 (4)
C9—P1—Cu1	120.27 (13)	C24—C25—H25	120.0
C27—P2—C33	104.65 (19)	C26—C25—H25	120.0
C27—P2—C39	102.86 (19)	C21—C26—C25	120.7 (4)
C33—P2—C39	101.65 (19)	C21—C26—H26	119.7
C27—P2—Cu1	115.37 (14)	C25—C26—H26	119.7
C33—P2—Cu1	113.70 (14)	C28—C27—C32	118.3 (4)
C39—P2—Cu1	116.85 (13)	C28—C27—P2	117.3 (3)
C1—S1—Cu1	110.32 (15)	C32—C27—P2	124.4 (4)
N2—C1—N1	106.0 (4)	C27—C28—C29	120.4 (5)
N2—C1—S1	128.4 (3)	C27—C28—H28	119.8
N1—C1—S1	125.6 (4)	C29—C28—H28	119.8
C7—C2—C3	121.3 (4)	C30—C29—C28	120.6 (6)
C7—C2—N2	133.6 (4)	C30—C29—H29	119.7
C3—C2—N2	105.2 (4)	C28—C29—H29	119.7
C2—C3—N1	107.2 (4)	C31—C30—C29	119.4 (6)
C2—C3—C4	121.0 (4)	C31—C30—H30	120.3
N1—C3—C4	131.8 (4)	C29—C30—H30	120.3
C5—C4—C3	117.9 (4)	C30—C31—C32	121.0 (6)
C5—C4—H4	121.0	C30—C31—H31	119.5
C3—C4—H4	121.0	C32—C31—H31	119.5
C6—C5—C4	119.6 (4)	C31—C32—C27	120.3 (5)
C6—C5—C8	120.0 (5)	C31—C32—H32	119.9
C4—C5—C8	120.5 (5)	C27—C32—H32	119.9
C7—C6—C5	122.7 (5)	C34—C33—C38	118.0 (4)
C7—C6—H6	118.7	C34—C33—P2	118.1 (3)
C5—C6—H6	118.7	C38—C33—P2	123.9 (3)
C2—C7—C6	117.5 (5)	C33—C34—C35	120.8 (4)
C2—C7—H7	121.2	C33—C34—H34	119.6
C6—C7—H7	121.2	C35—C34—H34	119.6
C5—C8—H8A	109.5	C36—C35—C34	120.6 (5)
C5—C8—H8B	109.5	C36—C35—H35	119.7
H8A—C8—H8B	109.5	C34—C35—H35	119.7
C5—C8—H8C	109.5	C37—C36—C35	119.4 (5)
H8A—C8—H8C	109.5	C37—C36—H36	120.3
H8B—C8—H8C	109.5	C35—C36—H36	120.3
C10—C9—C14	118.7 (4)	C36—C37—C38	120.6 (5)
C10—C9—P1	117.1 (3)	C36—C37—H37	119.7
C14—C9—P1	124.2 (4)	C38—C37—H37	119.7
C9—C10—C11	120.4 (5)	C33—C38—C37	120.6 (5)
C9—C10—H10	119.8	C33—C38—H38	119.7
C11—C10—H10	119.8	C37—C38—H38	119.7
C12—C11—C10	120.2 (5)	C40—C39—C44	117.9 (4)
C12—C11—H11	119.9	C40—C39—P2	124.4 (4)
C10—C11—H11	119.9	C44—C39—P2	117.6 (3)
C11—C12—C13	120.4 (5)	C39—C40—C41	121.0 (5)
C11—C12—H12	119.8	C39—C40—H40	119.5
C13—C12—H12	119.8	C41—C40—H40	119.5
C12—C13—C14	120.1 (5)	C42—C41—C40	119.8 (5)
C12—C13—H13	119.9	C42—C41—H41	120.1
C14—C13—H13	119.9	C40—C41—H41	120.1
C9—C14—C13	120.1 (5)	C41—C42—C43	120.4 (5)
C9—C14—H14	119.9	C41—C42—H42	119.8
C13—C14—H14	119.9	C43—C42—H42	119.8
C16—C15—C20	118.2 (4)	C42—C43—C44	119.9 (5)
C16—C15—P1	124.4 (3)	C42—C43—H43	120.1
C20—C15—P1	117.3 (3)	C44—C43—H43	120.1
C15—C16—C17	120.1 (4)	C43—C44—C39	120.9 (5)
C15—C16—H16	119.9	C43—C44—H44	119.5
C17—C16—H16	119.9	C39—C44—H44	119.5
C18—C17—C16	120.6 (5)	O1—C45—H45A	109.5
C18—C17—H17	119.7	O1—C45—H45B	109.5
C16—C17—H17	119.7	H45A—C45—H45B	109.5
C19—C18—C17	120.0 (5)	O1—C45—H45C	109.5
C19—C18—H18	120.0	H45A—C45—H45C	109.5
C17—C18—H18	120.0	H45B—C45—H45C	109.5
C18—C19—C20	120.3 (5)

P2—Cu1—P1—C15	−55.75 (15)	C20—C15—C16—C17	0.4 (6)
S1—Cu1—P1—C15	58.28 (14)	P1—C15—C16—C17	175.6 (3)
I1—Cu1—P1—C15	177.16 (14)	C15—C16—C17—C18	−0.3 (7)
P2—Cu1—P1—C21	−173.36 (13)	C16—C17—C18—C19	0.4 (7)
S1—Cu1—P1—C21	−59.33 (14)	C17—C18—C19—C20	−0.6 (8)
I1—Cu1—P1—C21	59.55 (14)	C18—C19—C20—C15	0.8 (7)
P2—Cu1—P1—C9	65.20 (17)	C16—C15—C20—C19	−0.6 (6)
S1—Cu1—P1—C9	179.23 (16)	P1—C15—C20—C19	−176.2 (3)
I1—Cu1—P1—C9	−61.90 (16)	C15—P1—C21—C26	−114.3 (3)
P1—Cu1—P2—C27	−69.86 (15)	C9—P1—C21—C26	137.9 (3)
S1—Cu1—P2—C27	175.81 (14)	Cu1—P1—C21—C26	6.6 (4)
I1—Cu1—P2—C27	55.97 (15)	C15—P1—C21—C22	66.4 (4)
P1—Cu1—P2—C33	169.21 (16)	C9—P1—C21—C22	−41.5 (4)
S1—Cu1—P2—C33	54.88 (17)	Cu1—P1—C21—C22	−172.8 (3)
I1—Cu1—P2—C33	−64.96 (16)	C26—C21—C22—C23	1.0 (7)
P1—Cu1—P2—C39	51.22 (16)	P1—C21—C22—C23	−179.6 (4)
S1—Cu1—P2—C39	−63.11 (16)	C21—C22—C23—C24	−0.9 (7)
I1—Cu1—P2—C39	177.05 (15)	C22—C23—C24—C25	−0.2 (8)
P1—Cu1—S1—C1	139.24 (16)	C23—C24—C25—C26	1.2 (8)
P2—Cu1—S1—C1	−92.61 (16)	C22—C21—C26—C25	−0.1 (6)
I1—Cu1—S1—C1	24.83 (16)	P1—C21—C26—C25	−179.5 (3)
C2—N2—C1—N1	−2.3 (5)	C24—C25—C26—C21	−1.0 (7)
C2—N2—C1—S1	178.6 (3)	C33—P2—C27—C28	150.5 (4)
C3—N1—C1—N2	2.0 (5)	C39—P2—C27—C28	−103.6 (4)
C3—N1—C1—S1	−178.8 (3)	Cu1—P2—C27—C28	24.8 (4)
Cu1—S1—C1—N2	−34.4 (4)	C33—P2—C27—C32	−29.7 (4)
Cu1—S1—C1—N1	146.7 (3)	C39—P2—C27—C32	76.2 (4)
C1—N2—C2—C7	−177.0 (5)	Cu1—P2—C27—C32	−155.4 (3)
C1—N2—C2—C3	1.7 (5)	C32—C27—C28—C29	−1.6 (8)
C7—C2—C3—N1	178.5 (4)	P2—C27—C28—C29	178.2 (4)
N2—C2—C3—N1	−0.4 (5)	C27—C28—C29—C30	1.7 (9)
C7—C2—C3—C4	−1.3 (7)	C28—C29—C30—C31	−0.8 (10)
N2—C2—C3—C4	179.8 (4)	C29—C30—C31—C32	−0.1 (9)
C1—N1—C3—C2	−1.0 (5)	C30—C31—C32—C27	0.1 (8)
C1—N1—C3—C4	178.7 (4)	C28—C27—C32—C31	0.7 (7)
C2—C3—C4—C5	0.7 (7)	P2—C27—C32—C31	−179.1 (4)
N1—C3—C4—C5	−179.0 (4)	C27—P2—C33—C34	−99.1 (4)
C3—C4—C5—C6	−0.2 (7)	C39—P2—C33—C34	154.1 (4)
C3—C4—C5—C8	−179.1 (5)	Cu1—P2—C33—C34	27.7 (4)
C4—C5—C6—C7	0.1 (8)	C27—P2—C33—C38	81.9 (5)
C8—C5—C6—C7	179.0 (5)	C39—P2—C33—C38	−24.9 (5)
C3—C2—C7—C6	1.2 (7)	Cu1—P2—C33—C38	−151.4 (4)
N2—C2—C7—C6	179.7 (5)	C38—C33—C34—C35	0.6 (8)
C5—C6—C7—C2	−0.6 (8)	P2—C33—C34—C35	−178.5 (4)
C15—P1—C9—C10	168.4 (3)	C33—C34—C35—C36	−1.5 (9)
C21—P1—C9—C10	−83.6 (3)	C34—C35—C36—C37	1.7 (11)
Cu1—P1—C9—C10	44.5 (4)	C35—C36—C37—C38	−1.1 (11)
C15—P1—C9—C14	−13.8 (4)	C34—C33—C38—C37	0.0 (9)
C21—P1—C9—C14	94.3 (4)	P2—C33—C38—C37	179.1 (5)
Cu1—P1—C9—C14	−137.7 (3)	C36—C37—C38—C33	0.3 (11)
C14—C9—C10—C11	−1.8 (7)	C27—P2—C39—C40	6.5 (4)
P1—C9—C10—C11	176.1 (4)	C33—P2—C39—C40	114.6 (4)
C9—C10—C11—C12	1.7 (8)	Cu1—P2—C39—C40	−121.0 (4)
C10—C11—C12—C13	−0.9 (8)	C27—P2—C39—C44	−176.4 (4)
C11—C12—C13—C14	0.3 (9)	C33—P2—C39—C44	−68.2 (4)
C10—C9—C14—C13	1.2 (7)	Cu1—P2—C39—C44	56.1 (4)
P1—C9—C14—C13	−176.6 (4)	C44—C39—C40—C41	1.4 (7)
C12—C13—C14—C9	−0.5 (8)	P2—C39—C40—C41	178.5 (4)
C21—P1—C15—C16	9.9 (4)	C39—C40—C41—C42	0.5 (8)
C9—P1—C15—C16	115.6 (3)	C40—C41—C42—C43	−2.0 (9)
Cu1—P1—C15—C16	−114.2 (3)	C41—C42—C43—C44	1.5 (9)
C21—P1—C15—C20	−174.9 (3)	C42—C43—C44—C39	0.5 (8)
C9—P1—C15—C20	−69.2 (3)	C40—C39—C44—C43	−1.9 (7)
Cu1—P1—C15—C20	61.0 (3)	P2—C39—C44—C43	−179.2 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.86	1.97	2.755 (7)	152
N2—H2···I1	0.86	2.80	3.539 (3)	145
O1—H1A···I1	0.82	2.67	3.469 (5)	164

Symmetry code: (i) x, y+1, z.

Experimental details

Crystal data
Chemical formula	[CuI(C₈H₈N₂S)(C₁₈H₁₅P)₂]·CH₄O
M_r	911.27
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	15.6081 (11), 10.5938 (8), 25.976 (2)
β (°)	96.919 (1)
V (Å³)	4263.8 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.40
Crystal size (mm)	0.43 × 0.38 × 0.35

Data collection
Diffractometer	Bruker APEX CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.585, 0.641
No. of measured, independent and observed [I > 2σ(I)] reflections	20808, 7504, 5465
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.088, 1.09
No. of reflections	7504
No. of parameters	478
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.75, −0.54

Computer programs: SMART (Bruker, 2007), SAINT-Plus (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.86	1.97	2.755 (7)	152
N2—H2···I1	0.86	2.80	3.539 (3)	145
O1—H1A···I1	0.82	2.67	3.469 (5)	164

Symmetry code: (i) x, y+1, z.

Acknowledgements

This work was supported by the National Natural Science Foundation of China (grant No. 21171119), the National High Technology Research and Development Program of China (863 Program) (2012 A A063201), Beijing Personnel Bureau, the National Keystone Basic Research Program (973 Program) (grant Nos. 2007CB310408 and 2006CB302901) and and the Committee of Education of the Beijing Foundation of China (grant No. KM201210028020).

References

Aslanidis, P., Hadjikakou, S. K., Karagiannidis, P., Gdaniec, M. & Kosturkiewicz, Z. (1993). Polyhedron, 12, 2221–2226. CSD CrossRef CAS Web of Science Google Scholar
Baxter, P., Lehn, J. M., Fischer, J. & Youinou, M. T. (1994). Angew. Chem. Int. Ed. Engl. 33, 2284–2287. CSD CrossRef Web of Science Google Scholar
Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2007). SMART and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Kitagawa, S., Kondo, M., Kawata, S., Wada, S., Maekawa, M. & Munakata, M. (1995). Inorg. Chem. 34, 1455–1465. CSD CrossRef CAS Web of Science Google Scholar
Lewis, J. S., Zweit, J., Dearling, J. L. J., Rooney, B. C. & Blower, P. J. (1996). Chem. Commun. pp. 1093–1094. CrossRef Web of Science Google Scholar
Li, D., Luo, Y.-F., Wu, T. & Ng, S. W. (2004). Acta Cryst. E60, m726–m727. Web of Science CSD CrossRef IUCr Journals Google Scholar
Lobana, T. S., Rekha, Sidhu, B.S., Castineiras, A., Bermejo, E. & Nishioka, T. (2005). J. Coord. Chem. 58, 803–809. Web of Science CSD CrossRef CAS Google Scholar
Ozturk, I. I., Hadjikakou, S. K., Hadjiliadis, N., Kourkoumelis, N., Kubicki, M., Tasiopoulos, A. J., Scleiman, H., Barsan, M. M., Butler, I. S. & Balzarini, J. (2009). Inorg. Chem. 48, 2233–2245. Web of Science CSD CrossRef PubMed CAS Google Scholar
Schneider, J., Lee, Y. A., Perez, J., Brennessel, W. W., Flaschenriem, C. & Eisenberg, R. (2008). Inorg. Chem. 47, 957–968. Web of Science CSD CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 10| October 2012| Page m1295

https://doi.org/10.1107/S1600536812039165

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Iodido[5-methyl-1H-benzimidazole-2(3H)-thione-κS]bis­­(tri­phenyl­phosphane-κP)copper(I) methanol monosolvate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Iodido[5-methyl-1H-benzimidazole-2(3H)-thione-κS]bis(triphenylphosphane-κP)copper(I) methanol monosolvate