(N,N-Diethyl­dithio­carbamato-κ2S,S′)iodido(1,10-phenanthroline-κ2N,N′)copper(II)

Fan, L.-Q.; Wu, J.-H.; Huang, Y.-F.; Ng, S.W.

doi:10.1107/S160053680903637X

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 10| October 2009| Page m1209

doi:10.1107/S160053680903637X

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(N,N-Diethyldithiocarbamato-κ²S,S′)iodido(1,10-phenanthroline-κ²N,N′)copper(II)

Le-Qing Fan,^a ^* Ji-Huai Wu,^a Yun-Fang Huang ^a and Seik Weng Ng ^b

^aInstitute of Materials Physical Chemistry, Huaqiao University, Quanzhou, Fujian 362021, People's Republic of China, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: lqfan@hqu.edu.cn

(Received 8 September 2009; accepted 9 September 2009; online 12 September 2009)

The copper(II) atom in the title compound, [Cu(C₅H₁₀NS₂)I(C₁₂H₈N₂)], is chelated by the N-heterocycle and the dithiocarbamate anion in a slightly distorted tetragonal coordination. The tetragonal-pyramidal coorination is completed by the iodine atom in the apical position. One ethyl group is disordered over two positions with site occupancies of 0.31 (2) and 0.69 (2).

Related literature

For the crystal structures of other N,N′-chelated dithiocarbamatocopper adducts of N-heterocycles, see: Fan & Wu (2008 , 2009 ).

Experimental

Crystal data

[Cu(C₅H₁₀NS₂)I(C₁₂H₈N₂)]
M_r = 518.90
Monoclinic, P 2₁ /c
a = 15.357 (5) Å
b = 9.252 (3) Å
c = 14.153 (5) Å
β = 103.741 (5)°
V = 1953.3 (11) Å³
Z = 4
Mo Kα radiation
μ = 2.92 mm⁻¹
T = 293 K
0.20 × 0.20 × 0.10 mm

Data collection

Rigaku Mercury diffractometer
Absorption correction: multi-scan CrystalClear (Rigaku, 2007 ) T_min = 0.593, T_max = 0.759
14774 measured reflections
4470 independent reflections
3666 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.116
S = 0.93
4470 reflections
237 parameters
H-atom parameters constrained
Δρ_max = 0.44 e Å⁻³
Δρ_min = −0.73 e Å⁻³

Data collection: CrystalClear (Rigaku, 2007); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680903637X/bt5056sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680903637X/bt5056Isup2.hkl

checkCIF report

Related literature top

For the crystal structures of other N,N'-chelated dithiocarbamatocopper adducts of N-heterocycles, see: Fan & Wu (2008, 2009).

Experimental top

A mixture of copper(II) acetate hydrate (0.08 g, 0.4 mmol), sodium diethyldithiocarbamate trihydrate (0.09 g, 0.4 mmol), 1,10-phenanthroline (0.08 g 0.4 mmol) and sodium iodide dihydrate (0.07 g, 0.4 mmol) was stirred in DMF (15 ml). 2-Propanol was diffused into the solution; crystals were isolated after several days, yielding single crystals.

Computing details top

Data collection: CrystalClear (Rigaku, 2007); cell refinement: CrystalClear (Rigaku, 2007); data reduction: CrystalClear (Rigaku, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top

Fig. 1. Anisotropic displacement ellipsoid plot (Barbour, 2001) of CuI(C₁₂H₈N₂)(C₅H₁₀NS₂) at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius. The minor occupied sites of the disordered ethyl chain is not shown.

(N,N-Diethyldithiocarbamato-κ²S,S')iodido(1,10-phenanthroline-κ²N,N')copper(II) top

Crystal data top

[Cu(C₅H₁₀NS₂)I(C₁₂H₈N₂)]	F(000) = 1020
M_r = 518.90	D_x = 1.764 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4020 reflections
a = 15.357 (5) Å	θ = 3.1–27.5°
b = 9.252 (3) Å	µ = 2.92 mm⁻¹
c = 14.153 (5) Å	T = 293 K
β = 103.741 (5)°	Prism, black
V = 1953.3 (11) Å³	0.20 × 0.20 × 0.10 mm
Z = 4

Data collection top

Rigaku Mercury diffractometer	4470 independent reflections
Radiation source: fine-focus sealed tube	3666 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
ω scans	θ_max = 27.5°, θ_min = 2.6°
Absorption correction: multi-scan CrystalClear (Rigaku, 2007)	h = −15→19
T_min = 0.593, T_max = 0.759	k = −12→12
14774 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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.116	H-atom parameters constrained
S = 0.93	w = 1/[σ²(F_o²) + (0.0613P)² + 3.3876P] where P = (F_o² + 2F_c²)/3
4470 reflections	(Δ/σ)_max = 0.001
237 parameters	Δρ_max = 0.44 e Å⁻³
0 restraints	Δρ_min = −0.73 e Å⁻³

Crystal data top

[Cu(C₅H₁₀NS₂)I(C₁₂H₈N₂)]	V = 1953.3 (11) Å³
M_r = 518.90	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 15.357 (5) Å	µ = 2.92 mm⁻¹
b = 9.252 (3) Å	T = 293 K
c = 14.153 (5) Å	0.20 × 0.20 × 0.10 mm
β = 103.741 (5)°

Data collection top

Rigaku Mercury diffractometer	4470 independent reflections
Absorption correction: multi-scan CrystalClear (Rigaku, 2007)	3666 reflections with I > 2σ(I)
T_min = 0.593, T_max = 0.759	R_int = 0.033
14774 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.116	H-atom parameters constrained
S = 0.93	Δρ_max = 0.44 e Å⁻³
4470 reflections	Δρ_min = −0.73 e Å⁻³
237 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	Occ. (<1)
Cu1	0.28574 (4)	0.83518 (6)	0.45653 (4)	0.04622 (16)
I1	0.17818 (2)	0.58393 (3)	0.47531 (2)	0.05255 (13)
S1	0.37150 (9)	0.78291 (19)	0.34872 (9)	0.0680 (4)
S2	0.42493 (9)	0.78293 (18)	0.55491 (9)	0.0645 (4)
N1	0.5328 (3)	0.6852 (6)	0.4466 (3)	0.0682 (13)
N2	0.1835 (2)	0.9450 (4)	0.3643 (2)	0.0418 (8)
N3	0.2373 (2)	0.9449 (4)	0.5572 (2)	0.0412 (8)
C1	0.4550 (3)	0.7443 (5)	0.4495 (3)	0.0506 (11)
C2	0.5523 (8)	0.6281 (16)	0.3563 (8)	0.078 (4)	0.69 (2)
H2A	0.5786	0.5327	0.3692	0.094*	0.69 (2)
H2B	0.4964	0.6180	0.3075	0.094*	0.69 (2)
C2'	0.5643 (15)	0.726 (3)	0.3480 (16)	0.065 (7)	0.31 (2)
H2D	0.5231	0.7918	0.3066	0.077*	0.31 (2)
H2E	0.6246	0.7645	0.3617	0.077*	0.31 (2)
C3'	0.559 (2)	0.569 (3)	0.305 (2)	0.113 (13)	0.31 (2)
H3D	0.6181	0.5292	0.3151	0.170*	0.31 (2)
H3E	0.5320	0.5725	0.2361	0.170*	0.31 (2)
H3F	0.5232	0.5092	0.3362	0.170*	0.31 (2)
C3	0.6108 (13)	0.716 (2)	0.3191 (10)	0.150 (8)	0.69 (2)
H3A	0.6161	0.6792	0.2574	0.224*	0.69 (2)
H3B	0.6687	0.7172	0.3636	0.224*	0.69 (2)
H3C	0.5874	0.8130	0.3109	0.224*	0.69 (2)
C4	0.6012 (3)	0.6512 (6)	0.5367 (4)	0.0620 (13)
H4A	0.6346	0.5664	0.5257	0.074*
H4B	0.5713	0.6284	0.5881	0.074*
C5	0.6644 (4)	0.7723 (7)	0.5687 (5)	0.0799 (18)
`H5B	0.6313	0.8586	0.5744	0.120*
H5A	0.6994	0.7874	0.5217	0.120*
H5C	0.7033	0.7495	0.6306	0.120*
C6	0.1575 (4)	0.9422 (5)	0.2673 (3)	0.0509 (11)
H6	0.1914	0.8907	0.2325	0.061*
C7	0.0802 (4)	1.0150 (5)	0.2165 (3)	0.0560 (12)
H7	0.0629	1.0093	0.1490	0.067*
C8	0.0309 (3)	1.0935 (5)	0.2656 (4)	0.0518 (11)
H8	−0.0206	1.1413	0.2322	0.062*
C9	0.0586 (3)	1.1019 (4)	0.3680 (3)	0.0419 (9)
C10	0.1346 (3)	1.0248 (4)	0.4133 (3)	0.0375 (8)
C11	0.0123 (3)	1.1834 (5)	0.4272 (4)	0.0520 (11)
H11	−0.0384	1.2358	0.3971	0.062*
C12	0.0400 (3)	1.1862 (5)	0.5249 (4)	0.0512 (11)
H12	0.0085	1.2408	0.5609	0.061*
C13	0.1176 (3)	1.1058 (4)	0.5741 (3)	0.0425 (9)
C14	0.1639 (3)	1.0261 (4)	0.5176 (3)	0.0383 (9)
C15	0.1484 (4)	1.0955 (5)	0.6757 (3)	0.0521 (11)
H15	0.1197	1.1463	0.7162	0.062*
C16	0.2204 (4)	1.0107 (6)	0.7144 (3)	0.0558 (12)
H16	0.2403	1.0012	0.7815	0.067*
C17	0.2640 (3)	0.9384 (5)	0.6528 (3)	0.0489 (11)
H17	0.3142	0.8830	0.6802	0.059*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0399 (3)	0.0589 (3)	0.0391 (3)	0.0118 (2)	0.0078 (2)	−0.0028 (2)
I1	0.0471 (2)	0.0563 (2)	0.0574 (2)	0.00439 (14)	0.01878 (15)	0.00145 (13)
S1	0.0460 (7)	0.1134 (12)	0.0443 (6)	0.0092 (7)	0.0103 (5)	−0.0187 (7)
S2	0.0442 (7)	0.1012 (11)	0.0461 (6)	0.0208 (7)	0.0069 (5)	−0.0011 (6)
N1	0.040 (2)	0.098 (4)	0.067 (3)	0.007 (2)	0.015 (2)	−0.017 (2)
N2	0.040 (2)	0.0471 (19)	0.0377 (18)	0.0040 (16)	0.0087 (15)	0.0007 (14)
N3	0.0367 (19)	0.0460 (19)	0.0403 (18)	0.0073 (15)	0.0080 (15)	0.0029 (14)
C1	0.041 (2)	0.059 (3)	0.052 (3)	−0.001 (2)	0.013 (2)	−0.013 (2)
C2	0.073 (7)	0.090 (9)	0.076 (7)	0.025 (6)	0.027 (5)	−0.016 (7)
C2'	0.055 (12)	0.071 (15)	0.079 (14)	0.012 (10)	0.038 (10)	−0.008 (11)
C3'	0.18 (3)	0.085 (19)	0.090 (19)	0.055 (19)	0.072 (19)	0.024 (14)
C3	0.161 (16)	0.207 (19)	0.099 (10)	−0.075 (14)	0.066 (10)	0.007 (10)
C4	0.044 (3)	0.057 (3)	0.086 (4)	0.004 (2)	0.017 (3)	0.002 (3)
C5	0.063 (4)	0.087 (4)	0.083 (4)	−0.018 (3)	0.006 (3)	0.008 (3)
C6	0.059 (3)	0.055 (3)	0.039 (2)	0.001 (2)	0.012 (2)	−0.0020 (19)
C7	0.064 (3)	0.057 (3)	0.040 (2)	0.002 (3)	−0.002 (2)	0.006 (2)
C8	0.051 (3)	0.043 (2)	0.056 (3)	0.004 (2)	0.001 (2)	0.010 (2)
C9	0.039 (2)	0.039 (2)	0.046 (2)	−0.0002 (18)	0.0063 (18)	0.0026 (17)
C10	0.036 (2)	0.0368 (19)	0.039 (2)	−0.0013 (17)	0.0071 (16)	0.0020 (16)
C11	0.043 (3)	0.044 (2)	0.068 (3)	0.008 (2)	0.012 (2)	0.003 (2)
C12	0.048 (3)	0.042 (2)	0.064 (3)	0.006 (2)	0.015 (2)	−0.008 (2)
C13	0.039 (2)	0.039 (2)	0.051 (2)	−0.0017 (18)	0.0134 (19)	−0.0040 (17)
C14	0.039 (2)	0.0357 (19)	0.041 (2)	−0.0028 (17)	0.0105 (17)	−0.0018 (16)
C15	0.058 (3)	0.056 (3)	0.047 (2)	−0.002 (2)	0.021 (2)	−0.011 (2)
C16	0.066 (3)	0.064 (3)	0.036 (2)	−0.001 (3)	0.011 (2)	−0.004 (2)
C17	0.052 (3)	0.058 (3)	0.035 (2)	0.008 (2)	0.0066 (19)	0.0001 (18)

Geometric parameters (Å, º) top

Cu1—N3	2.030 (4)	C4—C5	1.481 (8)
Cu1—N2	2.057 (3)	C4—H4A	0.9700
Cu1—S1	2.2916 (15)	C4—H4B	0.9700
Cu1—S2	2.3082 (14)	C5—`H5B	0.9600
Cu1—I1	2.9002 (10)	C5—H5A	0.9600
S1—C1	1.714 (5)	C5—H5C	0.9600
S2—C1	1.701 (5)	C6—C7	1.405 (7)
N1—C1	1.324 (6)	C6—H6	0.9300
N1—C2	1.477 (12)	C7—C8	1.354 (7)
N1—C4	1.481 (7)	C7—H7	0.9300
N1—C2'	1.62 (2)	C8—C9	1.412 (6)
N2—C6	1.335 (5)	C8—H8	0.9300
N2—C10	1.355 (5)	C9—C10	1.388 (6)
N3—C17	1.319 (5)	C9—C11	1.435 (6)
N3—C14	1.359 (5)	C10—C14	1.438 (5)
C2—C3	1.41 (2)	C11—C12	1.347 (7)
C2—H2A	0.9700	C11—H11	0.9300
C2—H2B	0.9700	C12—C13	1.438 (6)
C2'—C3'	1.57 (4)	C12—H12	0.9300
C2'—H2D	0.9700	C13—C14	1.400 (6)
C2'—H2E	0.9700	C13—C15	1.406 (6)
C3'—H3D	0.9600	C15—C16	1.360 (7)
C3'—H3E	0.9600	C15—H15	0.9300
C3'—H3F	0.9600	C16—C17	1.390 (6)
C3—H3A	0.9600	C16—H16	0.9300
C3—H3B	0.9600	C17—H17	0.9300
C3—H3C	0.9600

N3—Cu1—N2	81.17 (14)	H3B—C3—H3C	109.5
N3—Cu1—S1	159.66 (12)	N1—C4—C5	112.4 (5)
N2—Cu1—S1	98.89 (11)	N1—C4—H4A	109.1
N3—Cu1—S2	97.04 (11)	C5—C4—H4A	109.1
N2—Cu1—S2	160.83 (11)	N1—C4—H4B	109.1
S1—Cu1—S2	76.18 (5)	C5—C4—H4B	109.1
N3—Cu1—I1	91.42 (11)	H4A—C4—H4B	107.9
N2—Cu1—I1	95.08 (11)	C4—C5—`H5B	109.5
S1—Cu1—I1	108.77 (5)	C4—C5—H5A	109.5
S2—Cu1—I1	104.06 (5)	`H5B—C5—H5A	109.5
C1—S1—Cu1	85.68 (16)	C4—C5—H5C	109.5
C1—S2—Cu1	85.43 (17)	`H5B—C5—H5C	109.5
C1—N1—C2	123.0 (6)	H5A—C5—H5C	109.5
C1—N1—C4	121.4 (4)	N2—C6—C7	121.8 (5)
C2—N1—C4	114.9 (6)	N2—C6—H6	119.1
C1—N1—C2'	112.7 (9)	C7—C6—H6	119.1
C2—N1—C2'	34.6 (8)	C8—C7—C6	120.2 (4)
C4—N1—C2'	119.6 (9)	C8—C7—H7	119.9
C6—N2—C10	118.0 (4)	C6—C7—H7	119.9
C6—N2—Cu1	129.8 (3)	C7—C8—C9	119.1 (4)
C10—N2—Cu1	112.1 (3)	C7—C8—H8	120.4
C17—N3—C14	118.3 (4)	C9—C8—H8	120.4
C17—N3—Cu1	128.4 (3)	C10—C9—C8	117.4 (4)
C14—N3—Cu1	113.1 (3)	C10—C9—C11	118.7 (4)
N1—C1—S2	123.3 (4)	C8—C9—C11	123.9 (4)
N1—C1—S1	124.2 (4)	N2—C10—C9	123.4 (4)
S2—C1—S1	112.4 (3)	N2—C10—C14	117.0 (4)
C3—C2—N1	113.3 (14)	C9—C10—C14	119.6 (4)
C3—C2—H2A	108.9	C12—C11—C9	122.0 (4)
N1—C2—H2A	108.9	C12—C11—H11	119.0
C3—C2—H2B	108.9	C9—C11—H11	119.0
N1—C2—H2B	108.9	C11—C12—C13	120.7 (4)
H2A—C2—H2B	107.7	C11—C12—H12	119.7
C3'—C2'—N1	97 (2)	C13—C12—H12	119.7
C3'—C2'—H2D	112.3	C14—C13—C15	117.1 (4)
N1—C2'—H2D	112.3	C14—C13—C12	118.1 (4)
C3'—C2'—H2E	112.3	C15—C13—C12	124.7 (4)
N1—C2'—H2E	112.3	N3—C14—C13	122.6 (4)
H2D—C2'—H2E	109.9	N3—C14—C10	116.5 (4)
C2'—C3'—H3D	109.5	C13—C14—C10	120.9 (4)
C2'—C3'—H3E	109.5	C16—C15—C13	119.6 (4)
H3D—C3'—H3E	109.5	C16—C15—H15	120.2
C2'—C3'—H3F	109.5	C13—C15—H15	120.2
H3D—C3'—H3F	109.5	C15—C16—C17	119.5 (4)
H3E—C3'—H3F	109.5	C15—C16—H16	120.3
C2—C3—H3A	109.5	C17—C16—H16	120.3
C2—C3—H3B	109.5	N3—C17—C16	122.9 (4)
H3A—C3—H3B	109.5	N3—C17—H17	118.6
C2—C3—H3C	109.5	C16—C17—H17	118.6
H3A—C3—H3C	109.5

N3—Cu1—S1—C1	76.2 (4)	C1—N1—C4—C5	−90.7 (7)
N2—Cu1—S1—C1	164.8 (2)	C2—N1—C4—C5	98.3 (9)
S2—Cu1—S1—C1	3.66 (18)	C2'—N1—C4—C5	59.5 (13)
I1—Cu1—S1—C1	−96.74 (18)	C10—N2—C6—C7	−2.1 (7)
N3—Cu1—S2—C1	−164.2 (2)	Cu1—N2—C6—C7	174.0 (4)
N2—Cu1—S2—C1	−80.8 (4)	N2—C6—C7—C8	1.5 (8)
S1—Cu1—S2—C1	−3.69 (18)	C6—C7—C8—C9	0.5 (8)
I1—Cu1—S2—C1	102.57 (18)	C7—C8—C9—C10	−1.7 (7)
N3—Cu1—N2—C6	−179.5 (4)	C7—C8—C9—C11	179.1 (5)
S1—Cu1—N2—C6	21.1 (4)	C6—N2—C10—C9	0.8 (6)
S2—Cu1—N2—C6	94.5 (5)	Cu1—N2—C10—C9	−175.9 (3)
I1—Cu1—N2—C6	−88.8 (4)	C6—N2—C10—C14	−180.0 (4)
N3—Cu1—N2—C10	−3.2 (3)	Cu1—N2—C10—C14	3.2 (5)
S1—Cu1—N2—C10	−162.6 (3)	C8—C9—C10—N2	1.1 (6)
S2—Cu1—N2—C10	−89.2 (4)	C11—C9—C10—N2	−179.7 (4)
I1—Cu1—N2—C10	87.5 (3)	C8—C9—C10—C14	−178.1 (4)
N2—Cu1—N3—C17	177.5 (4)	C11—C9—C10—C14	1.2 (6)
S1—Cu1—N3—C17	−90.7 (5)	C10—C9—C11—C12	−0.5 (7)
S2—Cu1—N3—C17	−21.7 (4)	C8—C9—C11—C12	178.7 (5)
I1—Cu1—N3—C17	82.6 (4)	C9—C11—C12—C13	−0.5 (7)
N2—Cu1—N3—C14	2.6 (3)	C11—C12—C13—C14	0.8 (7)
S1—Cu1—N3—C14	94.4 (4)	C11—C12—C13—C15	−176.1 (5)
S2—Cu1—N3—C14	163.3 (3)	C17—N3—C14—C13	1.8 (6)
I1—Cu1—N3—C14	−92.3 (3)	Cu1—N3—C14—C13	177.3 (3)
C2—N1—C1—S2	168.7 (8)	C17—N3—C14—C10	−177.2 (4)
C4—N1—C1—S2	−1.5 (8)	Cu1—N3—C14—C10	−1.7 (5)
C2'—N1—C1—S2	−153.6 (11)	C15—C13—C14—N3	−1.9 (6)
C2—N1—C1—S1	−8.1 (10)	C12—C13—C14—N3	−179.0 (4)
C4—N1—C1—S1	−178.4 (4)	C15—C13—C14—C10	177.0 (4)
C2'—N1—C1—S1	29.5 (12)	C12—C13—C14—C10	−0.1 (6)
Cu1—S2—C1—N1	−172.0 (5)	N2—C10—C14—N3	−1.1 (5)
Cu1—S2—C1—S1	5.2 (3)	C9—C10—C14—N3	178.1 (4)
Cu1—S1—C1—N1	172.0 (5)	N2—C10—C14—C13	179.9 (4)
Cu1—S1—C1—S2	−5.2 (3)	C9—C10—C14—C13	−0.9 (6)
C1—N1—C2—C3	106.4 (13)	C14—C13—C15—C16	0.1 (7)
C4—N1—C2—C3	−82.7 (14)	C12—C13—C15—C16	177.0 (5)
C2'—N1—C2—C3	23.9 (18)	C13—C15—C16—C17	1.7 (7)
C1—N1—C2'—C3'	−114.7 (15)	C14—N3—C17—C16	0.1 (7)
C2—N1—C2'—C3'	1.0 (16)	Cu1—N3—C17—C16	−174.6 (4)
C4—N1—C2'—C3'	92.7 (17)	C15—C16—C17—N3	−1.8 (8)

Experimental details

Crystal data
Chemical formula	[Cu(C₅H₁₀NS₂)I(C₁₂H₈N₂)]
M_r	518.90
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	15.357 (5), 9.252 (3), 14.153 (5)
β (°)	103.741 (5)
V (Å³)	1953.3 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.92
Crystal size (mm)	0.20 × 0.20 × 0.10

Data collection
Diffractometer	Rigaku Mercury diffractometer
Absorption correction	Multi-scan CrystalClear (Rigaku, 2007)
T_min, T_max	0.593, 0.759
No. of measured, independent and observed [I > 2σ(I)] reflections	14774, 4470, 3666
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.116, 0.93
No. of reflections	4470
No. of parameters	237
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.44, −0.73

Computer programs: CrystalClear (Rigaku, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

Acknowledgements

This work was supported by the Young Talent Fund of Fujian Province (No. 2007 F3060).

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Fan, L.-Q. & Wu, J.-H. (2008). Acta Cryst. E64, m639. Web of Science CSD CrossRef IUCr Journals Google Scholar
Fan, L.-Q. & Wu, J.-H. (2009). Acta Cryst. E65, m319. Web of Science CSD CrossRef IUCr Journals Google Scholar
Rigaku (2007). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2009). publCIF. In preparation. Google Scholar

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