[4,6-Dimethyl­pyrimidine-2(1H)-thione-κS]iodidobis(triphenyl­phosphane-κP)copper(I)

Pakawatchai, C.; Wattanakanjana, Y.; Choto, P.; Nimthong, R.

doi:10.1107/S1600536812021010

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Pages m773-m774

doi:10.1107/S1600536812021010

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[4,6-Dimethylpyrimidine-2(1H)-thione-κS]iodidobis(triphenylphosphane-κP)copper(I)

Chaveng Pakawatchai,^a ^* Yupa Wattanakanjana,^b Patcharanan Choto ^a and Ruthairat Nimthong ^a

^aDepartment of Chemistry and Center for Innovation in Chemistry, Faculty of Science, Prince of Songkla University, Hat Yai, Songkhla 90112, Thailand, and ^bDepartment of Chemistry, Faculty of Science, Prince of Songkla University, Hat Yai 90112, Thailand
^*Correspondence e-mail: chaveng.p@psu.ac.th

(Received 2 May 2012; accepted 9 May 2012; online 16 May 2012)

In the mononuclear title complex, [CuI(C₆H₈N₂S)(C₁₈H₁₅P)₂], the Cu^I ion is in a slightly distorted tetrahedral coordination geometry formed by two P atoms from two triphenylphosphane ligands, one S atom from a 4,6-dimethylpyrimidine-2(1H)-thione ligand and one iodide ion. There is an intramolecular N—H⋯I hydrogen bond. In the crystal, π–π stacking interactions [centroid–centroid distance = 3.594 (1) Å] are observed.

Related literature

For the coordination and potential applications of Cu^I complexes, see: Santra et al. (1999 ); Fujisawa et al. (2004 ); Tian et al. (2004 ); Kang (2006 ); Reymond & Cossy (2008 ); Gong et al. (2010 ). For relevant examples of discrete complexes, see: Voutsas et al. (1995 ); Lemos et al. (2001 ); Lobana et al. (2008 ); Nimthong et al. (2008 ).

Experimental

Crystal data

[CuI(C₆H₈N₂S)(C₁₈H₁₅P)₂]
M_r = 855.18
Triclinic, $[P \overline 1]$
a = 11.5605 (7) Å
b = 13.0076 (8) Å
c = 13.6456 (8) Å
α = 92.243 (1)°
β = 99.247 (1)°
γ = 106.092 (1)°
V = 1938.3 (2) Å³
Z = 2
Mo Kα radiation
μ = 1.53 mm⁻¹
T = 293 K
0.32 × 0.16 × 0.08 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2003 ) T_min = 0.744, T_max = 0.882
26730 measured reflections
9368 independent reflections
8066 reflections with I > 2σ(I)
R_int = 0.019

Refinement

R[F² > 2σ(F²)] = 0.028
wR(F²) = 0.075
S = 1.03
9368 reflections
448 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.90 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯I1	0.87 (3)	2.62 (3)	3.4858 (18)	176 (3)

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008 ); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812021010/lh5472sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812021010/lh5472Isup2.hkl

checkCIF report

Comment top

The synthesis and coordination chemistry of copper(I) complexes have been widely studied. Some of these complexes have been found to have unusual structural features, exhibit corrosion-inhibiting properties (Tian et al., 2004), catalytic activity in photo-redox reactions (Santra et al., 1999), phosphorescence due to close Cu···Cu interactions (Gong, et al., 2010), precursors to blue copper–protein model (Fujisawa et al., 2004) and catalysts in enantiomer selective Diels–Alder reactions (Reymond & Cossy, 2008). Moreover, the role of copper(I) is evident in several biologically important reactions, such as a dioxygen carrier and models for several enzymes (Kang, 2006).

The molecular structure of the title compound is shown in Fig. 1. The complex is monomeric with a slightly distorted tetrahedral coordination enviroment around Cu1. The Cu1—S bond length of 2.3404 (6) Å, is in good agreement with values reported for other copper(I) complexes with heterocyclic thione ligands, such as 2.3723 (12) Å for [Cu(N₃)(dmpymtH)(PPh₃)₂] (Lemos et al., 2001) and 2.344 (3) Å for [CuI(1κs-imzsH)(PPh₃)₂] (Lobana et al., 2008). The Cu1—P1 and Cu1—P2 bond distances, 2.2897 (5) and 2.3047 (5) Å, are as expected. The bond distance of Cu1—I1, 2.6801 (3), is comparable to those found [2.6658 (8) Å] for [Cu₂(C₇H₈N₂S)(C₁₈ H₁₃P)₂I] (Nimthong et al., 2008) and 2.674 (2) Å for [Cu(PPh₃)₂(pymtH)I] (Voutsas et al., 1995). In the crystal, π(pyrimidine)···π(pyrimidine) (centroid-centroid distances = 3.594 Å) interactions are observed. In addition, an intramolecular hydrogen bond is also observed (see Table 1 and Fig. 2).

Related literature top

For the coordination and potential applications of Cu^I complexes, see: Santra et al. (1999); Fujisawa et al. (2004); Tian et al. (2004); Kang (2006); Reymond & Cossy (2008); Gong et al. (2010). For relevant examples of discrete complexes, see: Voutsas et al. (1995); Lemos et al. (2001); Lobana et al. (2008); Nimthong et al. (2008).

Experimental top

A solution of 4,6-dimethylpyrimidine-2(1H)-thione, (0.08 g, 0.52 mmol) in 30 cm³ of methanol was stirred at 333 K then CuI (0.10 g, 0.52 mmol) solid was added and stirred for 3 h. Solid of triphenylphosphane (0.27 g, 1.04 mmol) was added and heated with continuous stirring for a period of 2 h. The clear yellow solution was formed then filtered off and kept at room temperature. Slow evaporation of the solvent gave the yellow colored crystalline solids, which were filtered off and dried in vacuo. Analysis found: C 60.11, H 4.46, N 2.88, S 3.22%; calculated for C₄₂H₃₇CuIN₂P₂S: C 59.03, H 4.37, N 3.28, S 3.76%.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure with displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. Part of the crystal structure with the intramolecular hydrogen bond and π–π stacking interactions shown asphosphine dashed lines.

[4,6-Dimethylpyrimidine-2(1H)-thione- κS]iodidobis(triphenylphosphane-κP)copper(I) top

Crystal data top

[CuI(C₆H₈N₂S)(C₁₈H₁₅P)₂]	Z = 2
M_r = 855.18	F(000) = 864
Triclinic, P1	D_x = 1.465 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 11.5605 (7) Å	Cell parameters from 9368 reflections
b = 13.0076 (8) Å	θ = 1.5–28.1°
c = 13.6456 (8) Å	µ = 1.53 mm⁻¹
α = 92.243 (1)°	T = 293 K
β = 99.247 (1)°	Block, yellow
γ = 106.092 (1)°	0.32 × 0.16 × 0.08 mm
V = 1938.3 (2) Å³

Data collection top

Bruker SMART CCD diffractometer	9368 independent reflections
Radiation source: fine-focus sealed tube	8066 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.019
ϕ and ω scans	θ_max = 28.1°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2003)	h = −15→15
T_min = 0.744, T_max = 0.882	k = −17→17
26730 measured reflections	l = −18→18

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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.075	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.040P)² + 0.4017P] where P = (F_o² + 2F_c²)/3
9368 reflections	(Δ/σ)_max = 0.009
448 parameters	Δρ_max = 0.90 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

[CuI(C₆H₈N₂S)(C₁₈H₁₅P)₂]	γ = 106.092 (1)°
M_r = 855.18	V = 1938.3 (2) Å³
Triclinic, P1	Z = 2
a = 11.5605 (7) Å	Mo Kα radiation
b = 13.0076 (8) Å	µ = 1.53 mm⁻¹
c = 13.6456 (8) Å	T = 293 K
α = 92.243 (1)°	0.32 × 0.16 × 0.08 mm
β = 99.247 (1)°

Data collection top

Bruker SMART CCD diffractometer	9368 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2003)	8066 reflections with I > 2σ(I)
T_min = 0.744, T_max = 0.882	R_int = 0.019
26730 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	0 restraints
wR(F²) = 0.075	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.90 e Å⁻³
9368 reflections	Δρ_min = −0.26 e Å⁻³
448 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
C28	0.1739 (3)	0.7348 (2)	0.7628 (3)	0.0828 (9)
H28	0.1874	0.8068	0.7511	0.099*
N1	0.30622 (16)	0.47879 (16)	0.54816 (13)	0.0497 (4)
N2	0.50121 (16)	0.58089 (15)	0.62532 (14)	0.0522 (4)
I1	0.059857 (12)	0.249292 (11)	0.536351 (9)	0.05129 (5)
Cu1	0.20767 (2)	0.292271 (17)	0.714703 (16)	0.03664 (6)
P1	0.23312 (4)	0.13349 (4)	0.76683 (3)	0.03493 (10)
P2	0.11163 (4)	0.37674 (4)	0.81382 (3)	0.03521 (10)
S	0.40255 (5)	0.40670 (5)	0.71098 (4)	0.05366 (14)
C25	0.13677 (17)	0.52001 (15)	0.79783 (16)	0.0419 (4)
C36	0.2937 (2)	0.4210 (2)	0.97987 (18)	0.0589 (6)
H36	0.3434	0.4507	0.9349	0.071*
C31	0.16908 (18)	0.37741 (15)	0.94672 (14)	0.0413 (4)
C7	0.08651 (17)	0.04295 (14)	0.78284 (14)	0.0390 (4)
C13	0.33044 (18)	0.13894 (16)	0.88752 (14)	0.0413 (4)
C20	−0.12265 (19)	0.38591 (17)	0.84239 (16)	0.0479 (5)
H20	−0.0832	0.4533	0.8758	0.057*
C19	−0.05481 (16)	0.32710 (14)	0.80249 (13)	0.0361 (4)
C1A	0.40371 (17)	0.49478 (16)	0.62299 (15)	0.0436 (4)
C15	0.3912 (3)	0.0614 (3)	1.03790 (19)	0.0688 (7)
H15	0.3791	0.0047	1.0782	0.083*
C1	0.29216 (18)	0.05372 (14)	0.68461 (15)	0.0413 (4)
C24	−0.11585 (18)	0.22715 (16)	0.75210 (15)	0.0457 (4)
H24	−0.0721	0.1869	0.7244	0.055*
C12	0.0372 (2)	0.06523 (18)	0.86484 (17)	0.0519 (5)
H12	0.0823	0.1209	0.9125	0.062*
C23	−0.2420 (2)	0.18691 (19)	0.74285 (18)	0.0582 (6)
H23	−0.2822	0.1197	0.7093	0.070*
C30	0.1607 (2)	0.59860 (18)	0.8761 (2)	0.0595 (6)
H30	0.1647	0.5793	0.9412	0.071*
C4A	0.4968 (2)	0.64843 (17)	0.55446 (18)	0.0528 (5)
C3A	0.3966 (2)	0.63329 (19)	0.47959 (19)	0.0590 (6)
H3A	0.3960	0.6827	0.4322	0.071*
C21	−0.2480 (2)	0.3452 (2)	0.83287 (19)	0.0588 (6)
H21	−0.2924	0.3850	0.8603	0.071*
C26	0.1312 (2)	0.5507 (2)	0.70146 (18)	0.0577 (5)
H26	0.1153	0.4991	0.6481	0.069*
C6	0.3865 (2)	0.0101 (2)	0.7182 (2)	0.0607 (6)
H6	0.4233	0.0216	0.7850	0.073*
C14	0.3145 (2)	0.0530 (2)	0.94765 (17)	0.0549 (5)
H14	0.2518	−0.0100	0.9266	0.066*
C11	−0.0780 (2)	0.0054 (2)	0.8761 (2)	0.0636 (6)
H11	−0.1099	0.0205	0.9316	0.076*
C8	0.0176 (2)	−0.03985 (19)	0.71278 (18)	0.0577 (6)
H8	0.0489	−0.0563	0.6575	0.069*
C18	0.4263 (2)	0.23035 (18)	0.91961 (17)	0.0545 (5)
H18	0.4394	0.2878	0.8803	0.065*
C32	0.0970 (2)	0.33340 (18)	1.01459 (16)	0.0523 (5)
H32	0.0132	0.3033	0.9940	0.063*
C22	−0.3075 (2)	0.2458 (2)	0.78291 (19)	0.0608 (6)
H22	−0.3920	0.2186	0.7764	0.073*
C10	−0.1458 (2)	−0.0765 (2)	0.8056 (2)	0.0730 (7)
H10	−0.2236	−0.1167	0.8130	0.088*
C35	0.3454 (3)	0.4211 (3)	1.0784 (2)	0.0741 (8)
H35	0.4292	0.4510	1.0994	0.089*
C2	0.2401 (2)	0.03643 (19)	0.58387 (17)	0.0567 (5)
H2	0.1786	0.0671	0.5598	0.068*
C2A	0.2996 (2)	0.5461 (2)	0.47577 (18)	0.0589 (6)
C17	0.5035 (3)	0.2368 (2)	1.0107 (2)	0.0738 (8)
H17	0.5676	0.2988	1.0318	0.089*
C16	0.4861 (3)	0.1539 (3)	1.0685 (2)	0.0743 (8)
H16	0.5382	0.1592	1.1292	0.089*
C6A	0.6067 (3)	0.7428 (2)	0.5611 (3)	0.0796 (8)
H6A1	0.6128	0.7903	0.6185	0.119*
H6A2	0.5994	0.7801	0.5021	0.119*
H6A3	0.6787	0.7187	0.5668	0.119*
C33	0.1498 (3)	0.3341 (2)	1.11417 (18)	0.0693 (7)
H33	0.1009	0.3051	1.1599	0.083*
C34	0.2736 (3)	0.3774 (2)	1.1448 (2)	0.0761 (8)
H34	0.3085	0.3770	1.2111	0.091*
C5A	0.1858 (3)	0.5182 (3)	0.3989 (2)	0.1030 (13)
H5A1	0.1244	0.5432	0.4238	0.155*
H5A2	0.1567	0.4417	0.3840	0.155*
H5A3	0.2032	0.5519	0.3395	0.155*
C5	0.4258 (3)	−0.0509 (3)	0.6519 (3)	0.0819 (9)
H5	0.4898	−0.0793	0.6744	0.098*
C3	0.2792 (3)	−0.0261 (2)	0.5190 (2)	0.0716 (7)
H3	0.2428	−0.0384	0.4520	0.086*
C4	0.3712 (3)	−0.0695 (2)	0.5536 (2)	0.0793 (9)
H4	0.3969	−0.1119	0.5101	0.095*
C29	0.1787 (3)	0.7050 (2)	0.8583 (3)	0.0758 (8)
H29	0.1942	0.7569	0.9114	0.091*
C9	−0.0984 (2)	−0.0983 (2)	0.7250 (2)	0.0791 (8)
H9	−0.1446	−0.1534	0.6772	0.095*
C27	0.1490 (3)	0.6578 (2)	0.6843 (2)	0.0777 (8)
H27	0.1442	0.6777	0.6194	0.093*
H1N	0.247 (3)	0.420 (2)	0.547 (2)	0.078 (9)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C28	0.0644 (16)	0.0417 (13)	0.141 (3)	0.0128 (12)	0.0139 (18)	0.0234 (17)
N1	0.0387 (9)	0.0553 (11)	0.0455 (9)	0.0002 (8)	0.0018 (7)	0.0137 (8)
N2	0.0393 (9)	0.0523 (10)	0.0570 (11)	0.0014 (8)	0.0059 (8)	0.0074 (8)
I1	0.04691 (8)	0.05672 (9)	0.03803 (8)	0.00194 (6)	−0.00378 (5)	−0.00007 (6)
Cu1	0.03788 (12)	0.03647 (12)	0.03407 (11)	0.00853 (9)	0.00599 (9)	0.00272 (9)
P1	0.0365 (2)	0.0340 (2)	0.0347 (2)	0.00952 (18)	0.00871 (18)	0.00224 (18)
P2	0.0338 (2)	0.0356 (2)	0.0343 (2)	0.00938 (18)	0.00254 (18)	−0.00113 (18)
S	0.0366 (2)	0.0665 (3)	0.0475 (3)	0.0004 (2)	−0.0008 (2)	0.0205 (2)
C25	0.0321 (9)	0.0378 (9)	0.0543 (11)	0.0091 (7)	0.0050 (8)	0.0045 (8)
C36	0.0478 (12)	0.0735 (15)	0.0511 (13)	0.0197 (11)	−0.0040 (10)	−0.0108 (11)
C31	0.0464 (10)	0.0423 (10)	0.0352 (9)	0.0187 (8)	−0.0011 (8)	−0.0062 (7)
C7	0.0376 (9)	0.0364 (9)	0.0447 (10)	0.0111 (7)	0.0105 (8)	0.0078 (8)
C13	0.0419 (10)	0.0473 (10)	0.0392 (10)	0.0198 (8)	0.0076 (8)	0.0049 (8)
C20	0.0456 (11)	0.0457 (11)	0.0520 (12)	0.0134 (9)	0.0090 (9)	−0.0031 (9)
C19	0.0342 (9)	0.0399 (9)	0.0339 (9)	0.0105 (7)	0.0051 (7)	0.0033 (7)
C1A	0.0340 (9)	0.0501 (11)	0.0424 (10)	0.0052 (8)	0.0064 (8)	0.0063 (8)
C15	0.0698 (16)	0.093 (2)	0.0561 (14)	0.0397 (15)	0.0136 (12)	0.0321 (14)
C1	0.0449 (10)	0.0329 (9)	0.0487 (11)	0.0086 (8)	0.0206 (9)	0.0018 (8)
C24	0.0410 (10)	0.0466 (11)	0.0474 (11)	0.0099 (8)	0.0085 (8)	−0.0046 (8)
C12	0.0540 (12)	0.0546 (12)	0.0484 (12)	0.0127 (10)	0.0188 (10)	0.0042 (9)
C23	0.0449 (11)	0.0560 (13)	0.0625 (14)	−0.0012 (10)	0.0088 (10)	−0.0096 (11)
C30	0.0603 (14)	0.0433 (11)	0.0696 (15)	0.0089 (10)	0.0095 (12)	−0.0041 (10)
C4A	0.0460 (11)	0.0459 (11)	0.0656 (14)	0.0075 (9)	0.0174 (10)	0.0075 (10)
C3A	0.0579 (13)	0.0559 (13)	0.0653 (15)	0.0139 (11)	0.0169 (11)	0.0248 (11)
C21	0.0489 (12)	0.0665 (14)	0.0676 (15)	0.0228 (11)	0.0197 (11)	−0.0006 (12)
C26	0.0566 (13)	0.0569 (13)	0.0584 (13)	0.0179 (11)	0.0021 (11)	0.0128 (11)
C6	0.0605 (14)	0.0649 (15)	0.0646 (15)	0.0274 (12)	0.0188 (12)	0.0008 (12)
C14	0.0509 (12)	0.0621 (13)	0.0546 (13)	0.0191 (11)	0.0096 (10)	0.0175 (10)
C11	0.0568 (14)	0.0752 (16)	0.0663 (15)	0.0175 (12)	0.0318 (12)	0.0194 (13)
C8	0.0476 (12)	0.0582 (13)	0.0604 (14)	0.0034 (10)	0.0135 (10)	−0.0086 (11)
C18	0.0553 (13)	0.0501 (12)	0.0539 (13)	0.0164 (10)	−0.0042 (10)	0.0009 (10)
C32	0.0597 (13)	0.0524 (12)	0.0429 (11)	0.0169 (10)	0.0025 (9)	0.0044 (9)
C22	0.0376 (11)	0.0735 (16)	0.0674 (15)	0.0082 (10)	0.0136 (10)	0.0014 (12)
C10	0.0452 (13)	0.0726 (17)	0.097 (2)	0.0019 (12)	0.0246 (14)	0.0171 (15)
C35	0.0616 (15)	0.096 (2)	0.0607 (16)	0.0371 (15)	−0.0184 (13)	−0.0229 (14)
C2	0.0665 (14)	0.0596 (13)	0.0490 (12)	0.0225 (11)	0.0183 (11)	−0.0018 (10)
C2A	0.0535 (13)	0.0669 (15)	0.0515 (13)	0.0109 (11)	0.0041 (10)	0.0193 (11)
C17	0.0651 (16)	0.0727 (17)	0.0712 (17)	0.0201 (13)	−0.0208 (13)	−0.0064 (14)
C16	0.0705 (17)	0.103 (2)	0.0530 (14)	0.0422 (17)	−0.0090 (12)	0.0069 (14)
C6A	0.0615 (16)	0.0562 (15)	0.110 (2)	−0.0056 (12)	0.0211 (16)	0.0166 (15)
C33	0.095 (2)	0.0756 (17)	0.0410 (12)	0.0339 (15)	0.0062 (12)	0.0104 (11)
C34	0.099 (2)	0.089 (2)	0.0442 (13)	0.0519 (18)	−0.0173 (14)	−0.0088 (13)
C5A	0.0741 (19)	0.124 (3)	0.082 (2)	−0.0040 (19)	−0.0207 (16)	0.055 (2)
C5	0.083 (2)	0.085 (2)	0.099 (2)	0.0493 (17)	0.0372 (18)	0.0027 (17)
C3	0.0882 (19)	0.0708 (16)	0.0584 (15)	0.0197 (15)	0.0300 (14)	−0.0112 (12)
C4	0.094 (2)	0.0695 (17)	0.086 (2)	0.0278 (16)	0.0473 (18)	−0.0101 (15)
C29	0.0727 (17)	0.0385 (12)	0.110 (2)	0.0092 (12)	0.0121 (16)	−0.0065 (14)
C9	0.0520 (14)	0.0715 (17)	0.095 (2)	−0.0115 (12)	0.0176 (14)	−0.0172 (15)
C27	0.0728 (18)	0.0692 (18)	0.092 (2)	0.0231 (14)	0.0062 (15)	0.0383 (16)

Geometric parameters (Å, º) top

C28—C29	1.372 (5)	C4A—C6A	1.490 (3)
C28—C27	1.375 (5)	C3A—C2A	1.349 (3)
C28—H28	0.9300	C3A—H3A	0.9300
N1—C2A	1.352 (3)	C21—C22	1.377 (3)
N1—C1A	1.356 (3)	C21—H21	0.9300
N1—H1N	0.87 (3)	C26—C27	1.386 (3)
N2—C4A	1.336 (3)	C26—H26	0.9300
N2—C1A	1.346 (2)	C6—C5	1.390 (3)
I1—Cu1	2.6801 (3)	C6—H6	0.9300
Cu1—P1	2.2897 (5)	C14—H14	0.9300
Cu1—P2	2.3047 (5)	C11—C10	1.374 (4)
Cu1—S	2.3404 (6)	C11—H11	0.9300
P1—C13	1.826 (2)	C8—C9	1.385 (3)
P1—C7	1.8276 (19)	C8—H8	0.9300
P1—C1	1.8301 (18)	C18—C17	1.394 (3)
P2—C31	1.8271 (19)	C18—H18	0.9300
P2—C19	1.8306 (18)	C32—C33	1.396 (3)
P2—C25	1.832 (2)	C32—H32	0.9300
S—C1A	1.691 (2)	C22—H22	0.9300
C25—C26	1.386 (3)	C10—C9	1.359 (4)
C25—C30	1.388 (3)	C10—H10	0.9300
C36—C35	1.380 (3)	C35—C34	1.362 (4)
C36—C31	1.385 (3)	C35—H35	0.9300
C36—H36	0.9300	C2—C3	1.388 (3)
C31—C32	1.380 (3)	C2—H2	0.9300
C7—C8	1.381 (3)	C2A—C5A	1.491 (4)
C7—C12	1.390 (3)	C17—C16	1.350 (4)
C13—C18	1.381 (3)	C17—H17	0.9300
C13—C14	1.401 (3)	C16—H16	0.9300
C20—C21	1.380 (3)	C6A—H6A1	0.9600
C20—C19	1.391 (3)	C6A—H6A2	0.9600
C20—H20	0.9300	C6A—H6A3	0.9600
C19—C24	1.388 (3)	C33—C34	1.372 (4)
C15—C14	1.378 (3)	C33—H33	0.9300
C15—C16	1.382 (4)	C34—H34	0.9300
C15—H15	0.9300	C5A—H5A1	0.9600
C1—C6	1.387 (3)	C5A—H5A2	0.9600
C1—C2	1.392 (3)	C5A—H5A3	0.9600
C24—C23	1.389 (3)	C5—C4	1.369 (5)
C24—H24	0.9300	C5—H5	0.9300
C12—C11	1.380 (3)	C3—C4	1.365 (4)
C12—H12	0.9300	C3—H3	0.9300
C23—C22	1.372 (3)	C4—H4	0.9300
C23—H23	0.9300	C29—H29	0.9300
C30—C29	1.378 (3)	C9—H9	0.9300
C30—H30	0.9300	C27—H27	0.9300
C4A—C3A	1.379 (3)

C29—C28—C27	119.7 (2)	C25—C26—H26	119.8
C29—C28—H28	120.1	C27—C26—H26	119.8
C27—C28—H28	120.1	C1—C6—C5	120.0 (3)
C2A—N1—C1A	123.70 (19)	C1—C6—H6	120.0
C2A—N1—H1N	119.8 (19)	C5—C6—H6	120.0
C1A—N1—H1N	116.5 (19)	C15—C14—C13	120.3 (2)
C4A—N2—C1A	118.34 (19)	C15—C14—H14	119.8
P1—Cu1—P2	114.845 (19)	C13—C14—H14	119.8
P1—Cu1—S	107.14 (2)	C10—C11—C12	120.1 (2)
P2—Cu1—S	108.80 (2)	C10—C11—H11	119.9
P1—Cu1—I1	107.867 (15)	C12—C11—H11	119.9
P2—Cu1—I1	104.908 (15)	C7—C8—C9	119.9 (2)
S—Cu1—I1	113.453 (16)	C7—C8—H8	120.1
C13—P1—C7	102.91 (9)	C9—C8—H8	120.1
C13—P1—C1	102.99 (9)	C13—C18—C17	120.3 (2)
C7—P1—C1	104.14 (9)	C13—C18—H18	119.9
C13—P1—Cu1	117.33 (7)	C17—C18—H18	119.9
C7—P1—Cu1	110.26 (6)	C31—C32—C33	120.1 (2)
C1—P1—Cu1	117.49 (6)	C31—C32—H32	120.0
C31—P2—C19	104.15 (9)	C33—C32—H32	120.0
C31—P2—C25	102.49 (9)	C23—C22—C21	119.9 (2)
C19—P2—C25	102.70 (8)	C23—C22—H22	120.0
C31—P2—Cu1	112.72 (6)	C21—C22—H22	120.0
C19—P2—Cu1	118.86 (6)	C9—C10—C11	119.6 (2)
C25—P2—Cu1	114.09 (7)	C9—C10—H10	120.2
C1A—S—Cu1	113.57 (7)	C11—C10—H10	120.2
C26—C25—C30	118.6 (2)	C34—C35—C36	119.9 (3)
C26—C25—P2	117.47 (17)	C34—C35—H35	120.1
C30—C25—P2	123.89 (17)	C36—C35—H35	120.1
C35—C36—C31	121.2 (3)	C3—C2—C1	120.6 (2)
C35—C36—H36	119.4	C3—C2—H2	119.7
C31—C36—H36	119.4	C1—C2—H2	119.7
C32—C31—C36	118.4 (2)	C3A—C2A—N1	117.0 (2)
C32—C31—P2	124.09 (16)	C3A—C2A—C5A	125.5 (2)
C36—C31—P2	117.43 (17)	N1—C2A—C5A	117.5 (2)
C8—C7—C12	118.64 (19)	C16—C17—C18	120.6 (3)
C8—C7—P1	123.06 (15)	C16—C17—H17	119.7
C12—C7—P1	118.01 (15)	C18—C17—H17	119.7
C18—C13—C14	118.5 (2)	C17—C16—C15	120.2 (2)
C18—C13—P1	118.66 (16)	C17—C16—H16	119.9
C14—C13—P1	122.82 (17)	C15—C16—H16	119.9
C21—C20—C19	120.6 (2)	C4A—C6A—H6A1	109.5
C21—C20—H20	119.7	C4A—C6A—H6A2	109.5
C19—C20—H20	119.7	H6A1—C6A—H6A2	109.5
C24—C19—C20	118.64 (18)	C4A—C6A—H6A3	109.5
C24—C19—P2	118.91 (14)	H6A1—C6A—H6A3	109.5
C20—C19—P2	122.45 (15)	H6A2—C6A—H6A3	109.5
N2—C1A—N1	119.00 (18)	C34—C33—C32	120.2 (3)
N2—C1A—S	120.84 (15)	C34—C33—H33	119.9
N1—C1A—S	120.16 (15)	C32—C33—H33	119.9
C14—C15—C16	120.0 (2)	C35—C34—C33	120.1 (2)
C14—C15—H15	120.0	C35—C34—H34	119.9
C16—C15—H15	120.0	C33—C34—H34	119.9
C6—C1—C2	118.65 (19)	C2A—C5A—H5A1	109.5
C6—C1—P1	122.95 (17)	C2A—C5A—H5A2	109.5
C2—C1—P1	118.40 (16)	H5A1—C5A—H5A2	109.5
C19—C24—C23	120.29 (19)	C2A—C5A—H5A3	109.5
C19—C24—H24	119.9	H5A1—C5A—H5A3	109.5
C23—C24—H24	119.9	H5A2—C5A—H5A3	109.5
C11—C12—C7	120.6 (2)	C4—C5—C6	120.5 (3)
C11—C12—H12	119.7	C4—C5—H5	119.7
C7—C12—H12	119.7	C6—C5—H5	119.7
C22—C23—C24	120.3 (2)	C4—C3—C2	119.9 (3)
C22—C23—H23	119.8	C4—C3—H3	120.1
C24—C23—H23	119.8	C2—C3—H3	120.1
C29—C30—C25	120.6 (3)	C3—C4—C5	120.3 (2)
C29—C30—H30	119.7	C3—C4—H4	119.8
C25—C30—H30	119.7	C5—C4—H4	119.8
N2—C4A—C3A	122.6 (2)	C28—C29—C30	120.4 (3)
N2—C4A—C6A	116.1 (2)	C28—C29—H29	119.8
C3A—C4A—C6A	121.3 (2)	C30—C29—H29	119.8
C2A—C3A—C4A	119.3 (2)	C10—C9—C8	121.2 (3)
C2A—C3A—H3A	120.3	C10—C9—H9	119.4
C4A—C3A—H3A	120.3	C8—C9—H9	119.4
C22—C21—C20	120.2 (2)	C28—C27—C26	120.3 (3)
C22—C21—H21	119.9	C28—C27—H27	119.8
C20—C21—H21	119.9	C26—C27—H27	119.8
C25—C26—C27	120.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···I1	0.87 (3)	2.62 (3)	3.4858 (18)	176 (3)

Experimental details

Crystal data
Chemical formula	[CuI(C₆H₈N₂S)(C₁₈H₁₅P)₂]
M_r	855.18
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	11.5605 (7), 13.0076 (8), 13.6456 (8)
α, β, γ (°)	92.243 (1), 99.247 (1), 106.092 (1)
V (Å³)	1938.3 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.53
Crystal size (mm)	0.32 × 0.16 × 0.08

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2003)
T_min, T_max	0.744, 0.882
No. of measured, independent and observed [I > 2σ(I)] reflections	26730, 9368, 8066
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.662

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.075, 1.03
No. of reflections	9368
No. of parameters	448
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.90, −0.26

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 2003), SHELXS97 (Sheldrick, 2008), Mercury (Macrae et al., 2008), SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···I1	0.87 (3)	2.62 (3)	3.4858 (18)	176 (3)

Acknowledgements

We gratefully acknowledge financial support from the Center for Innovation in Chemistry (PERCH–CIC), the Commission on Higher Education, Ministry of Education, the Department of Chemistry and the Graduate School, Prince of Songkla University.

References

Bruker (1998). SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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Volume 68| Part 6| June 2012| Pages m773-m774

doi:10.1107/S1600536812021010

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

[4,6-Di­methyl­pyrimidine-2(1H)-thione-κS]iodidobis(tri­phenyl­phosphane-κP)copper(I)

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

[4,6-Dimethylpyrimidine-2(1H)-thione-κS]iodidobis(triphenylphosphane-κP)copper(I)