Bis{μ-(E)-methyl 4-[(2-carbamothio­ylhydrazinyl­idene)meth­yl]benzoate-κ2S:S}bis­[iodido(triphenyl­phosphane-κP)copper(I)]

Mandal, S.; Nethi, V.; Gupta, P.

doi:10.1107/S1600536811041845

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page m1535

doi:10.1107/S1600536811041845

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Bis{μ-(E)-methyl 4-[(2-carbamothioylhydrazinylidene)methyl]benzoate-κ²S:S}bis[iodido(triphenylphosphane-κP)copper(I)]

Soumik Mandal,^a Vamsidhar Nethi ^a and Parna Gupta ^a ^*

^aDepartment of Chemical Sciences, IISER Kolkata, Mohanpur Campus, 741 252 West Bengal, India
^*Correspondence e-mail: parna@iiserkol.ac.in

(Received 30 August 2011; accepted 11 October 2011; online 12 October 2011)

The title complex, [Cu₂I₂(C₁₀H₁₁N₃O₂S)₂(C₁₈H₁₅P)₂], is a centrosymmetric sulfur-bridged dimer of Cu^I with PPh₃ and iodine. The Cu^I atom shows a distorted tetrahedral geometry, with bite angles ranging from 98.61 (2) to 120.16 (3)°. The intramolecular Cu⋯Cu distance is 2.8228 (12) Å. The thiosemicarbazone ligand is coordinated only through the S atom. In the crystal, the complex molecules are linked via intermolecular N—H⋯O hydrogen bonds, resulting in a hydrogen-bonded chain along the b axis.

Related literature

For a related structure, see: Lobana et al. (2009 ). For the chemotherapeutic properties of transition metal complexes of thiosemicarbazones see: Quiroga et al. (1998 ). For binding modes of thiosemicarbazones, see: Dutta et al. (2008 ).

Experimental

Crystal data

[Cu₂I₂(C₁₀H₁₁N₃O₂S)₂(C₁₈H₁₅P)₂]
M_r = 1380.02
Triclinic, $[P \overline 1]$
a = 9.6319 (16) Å
b = 11.945 (2) Å
c = 13.581 (4) Å
α = 108.627 (4)°
β = 101.655 (4)°
γ = 105.044 (3)°
V = 1359.0 (5) Å³
Z = 1
Mo Kα radiation
μ = 2.11 mm⁻¹
T = 100 K
0.18 × 0.11 × 0.09 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008) T_min = 0.757, T_max = 0.827
22347 measured reflections
5922 independent reflections
4560 reflections with I > 2σ(I)
R_int = 0.065

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.073
S = 1.02
5922 reflections
335 parameters
H-atom parameters constrained
Δρ_max = 1.56 e Å⁻³
Δρ_min = −0.82 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3B⋯O1ⁱ	0.86	2.17	2.963 (5)	154
Symmetry code: (i) x, y+1, z.

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); 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/S1600536811041845/ds2140sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811041845/ds2140Isup2.hkl

checkCIF report

Comment top

Thiosemicarbazones and more specifically transition metal complexes of thiosemicarbazones (Lobana et al., 2009) are of considerable pharmacological interest as they have shown a broad spectrum of chemotherapeutic properties (Quiroga et al., 1998). Thiosemicarbazones usually bind to a metal ion in mono, bi or tridentate fashion (Dutta et al., 2008). Interestingly, one-dimensional network formation has been observed here, where the single unit contain two metal ion bridged by the sulfur atom of two ligands. Two phosphine molecules and two iodine molecules are also coordinated to the metal centre. The C—S bond length [C19—S1 (1.720 (3) Å), C20—N2 (1.282 (5) Å)] indicates presence of double-bond character.

Related literature top

For a related structure, see: Lobana et al. (2009). For the chemotherapeutic properties of transition metal complexes of thiosemicarbazones see: Quiroga et al. (1998). For binding modes of thiosemicarbazones, see: Dutta et al. (2008).

Experimental top

0.190 g(1.0 mmol) CuI was dissolved in 10 mL acetonitrile and 10 mL me thanol, and to this solution 0.237 g(1.0 mmol) Schiff's base of 4-formyl methyl benzoate and thiosemicarbazone was added and stirred for 2 h followed by the addition of 0.262 g(1.0 mmol) PPh₃. The mixture was stirred for another 2 h, filtered and kept for crystallization. From the yellow solution yellow coloured block shaped crystals were obtained suitable for x-ray crystallography.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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. Structure with 50% probability displacement ellipsoids.
	Fig. 2. One dimensional asoociation via intermolecular H-bonding between C═O and N—H proton.
	Fig. 3. The formation of the title compound.

Bis{µ-(E)-methyl 4-[(2-carbamothioylhydrazinylidene)methyl]benzoate- κ²S:S}bis[iodido(triphenylphosphane-κP)copper(I)] top

Crystal data top

[Cu₂I₂(C₁₀H₁₁N₃O₂S)₂(C₁₈H₁₅P)₂]	Z = 1
M_r = 1380.02	F(000) = 688
Triclinic, P1	D_x = 1.684 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.6319 (16) Å	Cell parameters from 4585 reflections
b = 11.945 (2) Å	θ = 2.3–28.2°
c = 13.581 (4) Å	µ = 2.11 mm⁻¹
α = 108.627 (4)°	T = 100 K
β = 101.655 (4)°	Block, yellow
γ = 105.044 (3)°	0.18 × 0.11 × 0.09 mm
V = 1359.0 (5) Å³

Data collection top

Bruker APEXII CCD diffractometer	5922 independent reflections
Radiation source: fine-focus sealed tube	4560 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.065
ϕ and ω scans	θ_max = 27.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −12→11
T_min = 0.757, T_max = 0.827	k = −14→15
22347 measured reflections	l = −17→17

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.073	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0265P)² + 0.8634P] where P = (F_o² + 2F_c²)/3
5922 reflections	(Δ/σ)_max = 0.001
335 parameters	Δρ_max = 1.56 e Å⁻³
0 restraints	Δρ_min = −0.82 e Å⁻³

Crystal data top

[Cu₂I₂(C₁₀H₁₁N₃O₂S)₂(C₁₈H₁₅P)₂]	γ = 105.044 (3)°
M_r = 1380.02	V = 1359.0 (5) Å³
Triclinic, P1	Z = 1
a = 9.6319 (16) Å	Mo Kα radiation
b = 11.945 (2) Å	µ = 2.11 mm⁻¹
c = 13.581 (4) Å	T = 100 K
α = 108.627 (4)°	0.18 × 0.11 × 0.09 mm
β = 101.655 (4)°

Data collection top

Bruker APEXII CCD diffractometer	5922 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	4560 reflections with I > 2σ(I)
T_min = 0.757, T_max = 0.827	R_int = 0.065
22347 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.073	H-atom parameters constrained
S = 1.02	Δρ_max = 1.56 e Å⁻³
5922 reflections	Δρ_min = −0.82 e Å⁻³
335 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	0.44847 (4)	0.99151 (4)	0.39202 (4)	0.01460 (11)
I1	0.44275 (2)	1.19639 (2)	0.35819 (2)	0.01695 (7)
S1	0.70887 (9)	1.06875 (7)	0.50340 (8)	0.01341 (19)
P1	0.36351 (9)	0.82308 (7)	0.23174 (8)	0.01134 (19)
O1	0.9554 (3)	0.1581 (2)	0.2812 (2)	0.0209 (6)
O2	1.0438 (3)	0.2624 (2)	0.1819 (2)	0.0216 (6)
N1	0.7579 (3)	0.8525 (2)	0.4633 (3)	0.0153 (7)
H1	0.7016	0.8385	0.5030	0.018*
N2	0.8214 (3)	0.7653 (3)	0.4179 (3)	0.0178 (7)
N3	0.8721 (3)	0.9774 (3)	0.3848 (3)	0.0190 (7)
H3A	0.9110	0.9222	0.3577	0.023*
H3B	0.8903	1.0452	0.3724	0.023*
C1	0.4266 (3)	0.8438 (3)	0.1181 (3)	0.0124 (7)
C2	0.3426 (4)	0.7719 (3)	0.0089 (3)	0.0158 (8)
H2	0.2443	0.7175	−0.0092	0.019*
C3	0.4045 (4)	0.7809 (3)	−0.0733 (3)	0.0187 (8)
H3	0.3484	0.7315	−0.1462	0.022*
C4	0.5499 (4)	0.8635 (3)	−0.0468 (3)	0.0177 (8)
H4	0.5918	0.8688	−0.1018	0.021*
C5	0.6322 (4)	0.9377 (3)	0.0606 (3)	0.0179 (8)
H5	0.7291	0.9942	0.0776	0.021*
C6	0.5724 (3)	0.9295 (3)	0.1446 (3)	0.0148 (8)
H6	0.6287	0.9804	0.2171	0.018*
C7	0.1577 (4)	0.7719 (3)	0.1779 (3)	0.0140 (7)
C8	0.0617 (4)	0.6465 (3)	0.1235 (3)	0.0193 (8)
H8	0.1016	0.5821	0.1127	0.023*
C9	−0.0938 (4)	0.6175 (3)	0.0851 (3)	0.0244 (9)
H9	−0.1572	0.5336	0.0494	0.029*
C10	−0.1549 (4)	0.7110 (3)	0.0992 (4)	0.0242 (9)
H10	−0.2590	0.6905	0.0733	0.029*
C11	−0.0610 (4)	0.8364 (3)	0.1523 (3)	0.0223 (9)
H11	−0.1018	0.9001	0.1607	0.027*
C12	0.0937 (4)	0.8664 (3)	0.1926 (3)	0.0186 (8)
H12	0.1560	0.9505	0.2300	0.022*
C13	0.3993 (3)	0.6799 (3)	0.2321 (3)	0.0120 (7)
C14	0.4589 (4)	0.6129 (3)	0.1569 (3)	0.0195 (8)
H14	0.4803	0.6399	0.1028	0.023*
C15	0.4858 (4)	0.5062 (3)	0.1631 (3)	0.0208 (9)
H15	0.5253	0.4623	0.1129	0.025*
C16	0.4549 (4)	0.4645 (3)	0.2425 (3)	0.0196 (8)
H16	0.4725	0.3925	0.2454	0.023*
C17	0.3975 (4)	0.5306 (3)	0.3180 (3)	0.0231 (9)
H17	0.3759	0.5026	0.3716	0.028*
C18	0.3722 (4)	0.6386 (3)	0.3138 (3)	0.0178 (8)
H18	0.3367	0.6839	0.3662	0.021*
C19	0.7841 (3)	0.9580 (3)	0.4455 (3)	0.0145 (8)
C20	0.7924 (4)	0.6687 (3)	0.4428 (3)	0.0176 (8)
H20	0.7346	0.6633	0.4894	0.021*
C21	0.8490 (4)	0.5666 (3)	0.3989 (3)	0.0166 (8)
C22	0.8040 (4)	0.4589 (3)	0.4212 (3)	0.0173 (8)
H22	0.7422	0.4548	0.4654	0.021*
C23	0.8497 (4)	0.3586 (3)	0.3787 (3)	0.0160 (8)
H23	0.8207	0.2882	0.3955	0.019*
C24	0.9396 (4)	0.3629 (3)	0.3104 (3)	0.0142 (8)
C25	0.9797 (4)	0.2505 (3)	0.2592 (3)	0.0157 (8)
C26	1.0860 (4)	0.1589 (3)	0.1253 (4)	0.0257 (9)
H26A	1.1516	0.1418	0.1774	0.038*
H26B	1.1378	0.1804	0.0768	0.038*
H26C	0.9969	0.0855	0.0838	0.038*
C27	0.9853 (4)	0.4709 (3)	0.2880 (3)	0.0197 (8)
H27	1.0460	0.4748	0.2430	0.024*
C28	0.9406 (4)	0.5719 (3)	0.3325 (3)	0.0206 (8)
H28	0.9721	0.6437	0.3179	0.025*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0178 (2)	0.01218 (19)	0.0124 (3)	0.00618 (16)	0.00386 (19)	0.00278 (18)
I1	0.02130 (12)	0.01412 (11)	0.01860 (16)	0.00695 (8)	0.00813 (10)	0.00863 (10)
S1	0.0140 (4)	0.0123 (4)	0.0132 (5)	0.0046 (3)	0.0041 (4)	0.0041 (3)
P1	0.0139 (4)	0.0109 (4)	0.0100 (5)	0.0060 (3)	0.0040 (4)	0.0036 (4)
O1	0.0301 (13)	0.0156 (12)	0.0252 (17)	0.0118 (10)	0.0147 (13)	0.0116 (12)
O2	0.0278 (13)	0.0214 (12)	0.0221 (17)	0.0139 (10)	0.0150 (13)	0.0080 (12)
N1	0.0185 (14)	0.0125 (13)	0.0210 (19)	0.0086 (11)	0.0123 (14)	0.0077 (13)
N2	0.0154 (13)	0.0147 (13)	0.023 (2)	0.0077 (11)	0.0086 (14)	0.0040 (13)
N3	0.0211 (15)	0.0206 (14)	0.024 (2)	0.0107 (12)	0.0140 (15)	0.0131 (14)
C1	0.0162 (15)	0.0109 (14)	0.015 (2)	0.0098 (12)	0.0073 (15)	0.0064 (14)
C2	0.0168 (16)	0.0126 (15)	0.017 (2)	0.0072 (13)	0.0058 (16)	0.0022 (15)
C3	0.0261 (18)	0.0211 (17)	0.012 (2)	0.0142 (14)	0.0053 (16)	0.0058 (16)
C4	0.0234 (17)	0.0262 (18)	0.018 (2)	0.0180 (15)	0.0133 (17)	0.0153 (17)
C5	0.0124 (15)	0.0228 (17)	0.027 (2)	0.0104 (13)	0.0082 (16)	0.0164 (17)
C6	0.0141 (15)	0.0163 (16)	0.016 (2)	0.0077 (13)	0.0043 (15)	0.0072 (15)
C7	0.0152 (16)	0.0154 (15)	0.010 (2)	0.0037 (12)	0.0035 (15)	0.0049 (14)
C8	0.0184 (17)	0.0156 (16)	0.024 (2)	0.0059 (13)	0.0089 (16)	0.0060 (16)
C9	0.0186 (17)	0.0183 (17)	0.030 (3)	−0.0011 (14)	0.0093 (18)	0.0066 (17)
C10	0.0131 (16)	0.031 (2)	0.028 (3)	0.0070 (14)	0.0061 (17)	0.0117 (18)
C11	0.0237 (18)	0.0280 (19)	0.022 (2)	0.0162 (15)	0.0084 (17)	0.0125 (18)
C12	0.0208 (17)	0.0131 (15)	0.017 (2)	0.0058 (13)	0.0029 (16)	0.0025 (15)
C13	0.0118 (15)	0.0122 (14)	0.009 (2)	0.0041 (12)	0.0017 (14)	0.0022 (14)
C14	0.0264 (18)	0.0204 (17)	0.017 (2)	0.0119 (15)	0.0106 (17)	0.0078 (16)
C15	0.0296 (19)	0.0184 (17)	0.020 (2)	0.0161 (15)	0.0096 (18)	0.0070 (16)
C16	0.0229 (17)	0.0137 (16)	0.022 (2)	0.0090 (14)	0.0035 (17)	0.0068 (16)
C17	0.033 (2)	0.0217 (18)	0.020 (2)	0.0105 (16)	0.0099 (19)	0.0133 (17)
C18	0.0258 (18)	0.0164 (16)	0.017 (2)	0.0115 (14)	0.0135 (17)	0.0069 (16)
C19	0.0113 (15)	0.0138 (15)	0.013 (2)	0.0022 (12)	0.0008 (14)	0.0015 (14)
C20	0.0157 (16)	0.0180 (16)	0.019 (2)	0.0063 (13)	0.0082 (16)	0.0057 (16)
C21	0.0165 (16)	0.0161 (16)	0.016 (2)	0.0051 (13)	0.0051 (16)	0.0047 (15)
C22	0.0147 (16)	0.0200 (17)	0.018 (2)	0.0057 (13)	0.0077 (15)	0.0068 (16)
C23	0.0142 (15)	0.0145 (15)	0.020 (2)	0.0033 (13)	0.0061 (16)	0.0090 (15)
C24	0.0143 (15)	0.0153 (15)	0.014 (2)	0.0055 (12)	0.0046 (15)	0.0060 (15)
C25	0.0146 (16)	0.0139 (15)	0.015 (2)	0.0031 (12)	0.0029 (15)	0.0034 (15)
C26	0.032 (2)	0.0228 (18)	0.028 (3)	0.0159 (16)	0.0186 (19)	0.0066 (18)
C27	0.0217 (17)	0.0209 (17)	0.024 (2)	0.0107 (14)	0.0132 (17)	0.0115 (17)
C28	0.0291 (19)	0.0164 (16)	0.023 (2)	0.0106 (14)	0.0127 (18)	0.0114 (16)

Geometric parameters (Å, º) top

Cu1—P1	2.2548 (10)	C9—C10	1.371 (5)
Cu1—S1ⁱ	2.4060 (10)	C9—H9	0.9300
Cu1—S1	2.4093 (10)	C10—C11	1.387 (5)
Cu1—I1	2.6423 (6)	C10—H10	0.9300
Cu1—Cu1ⁱ	2.8228 (12)	C11—C12	1.384 (5)
S1—C19	1.720 (3)	C11—H11	0.9300
S1—Cu1ⁱ	2.4059 (10)	C12—H12	0.9300
P1—C7	1.827 (3)	C13—C18	1.394 (5)
P1—C1	1.832 (4)	C13—C14	1.402 (5)
P1—C13	1.832 (3)	C14—C15	1.389 (5)
O1—C25	1.212 (4)	C14—H14	0.9300
O2—C25	1.347 (4)	C15—C16	1.377 (6)
O2—C26	1.437 (4)	C15—H15	0.9300
N1—C19	1.329 (4)	C16—C17	1.385 (5)
N1—N2	1.383 (4)	C16—H16	0.9300
N1—H1	0.8600	C17—C18	1.390 (5)
N2—C20	1.282 (5)	C17—H17	0.9300
N3—C19	1.325 (5)	C18—H18	0.9300
N3—H3A	0.8600	C20—C21	1.467 (5)
N3—H3B	0.8600	C20—H20	0.9300
C1—C2	1.390 (5)	C21—C28	1.387 (5)
C1—C6	1.402 (4)	C21—C22	1.395 (5)
C2—C3	1.388 (5)	C22—C23	1.377 (5)
C2—H2	0.9300	C22—H22	0.9300
C3—C4	1.384 (5)	C23—C24	1.394 (5)
C3—H3	0.9300	C23—H23	0.9300
C4—C5	1.372 (5)	C24—C27	1.400 (5)
C4—H4	0.9300	C24—C25	1.489 (5)
C5—C6	1.396 (5)	C26—H26A	0.9600
C5—H5	0.9300	C26—H26B	0.9600
C6—H6	0.9300	C26—H26C	0.9600
C7—C8	1.394 (4)	C27—C28	1.384 (5)
C7—C12	1.401 (5)	C27—H27	0.9300
C8—C9	1.391 (5)	C28—H28	0.9300
C8—H8	0.9300

P1—Cu1—S1ⁱ	104.59 (4)	C12—C11—C10	119.8 (3)
P1—Cu1—S1	120.16 (3)	C12—C11—H11	120.1
S1ⁱ—Cu1—S1	108.22 (3)	C10—C11—H11	120.1
P1—Cu1—I1	110.45 (3)	C11—C12—C7	120.9 (3)
S1ⁱ—Cu1—I1	115.32 (3)	C11—C12—H12	119.5
S1—Cu1—I1	98.61 (2)	C7—C12—H12	119.5
P1—Cu1—Cu1ⁱ	130.06 (4)	C18—C13—C14	118.4 (3)
S1ⁱ—Cu1—Cu1ⁱ	54.16 (3)	C18—C13—P1	118.5 (3)
S1—Cu1—Cu1ⁱ	54.05 (3)	C14—C13—P1	123.0 (3)
I1—Cu1—Cu1ⁱ	119.49 (2)	C15—C14—C13	120.1 (4)
C19—S1—Cu1ⁱ	113.92 (13)	C15—C14—H14	120.0
C19—S1—Cu1	106.03 (11)	C13—C14—H14	120.0
Cu1ⁱ—S1—Cu1	71.78 (3)	C16—C15—C14	121.0 (4)
C7—P1—C1	103.42 (17)	C16—C15—H15	119.5
C7—P1—C13	104.04 (14)	C14—C15—H15	119.5
C1—P1—C13	102.23 (15)	C15—C16—C17	119.5 (3)
C7—P1—Cu1	109.73 (12)	C15—C16—H16	120.2
C1—P1—Cu1	117.80 (11)	C17—C16—H16	120.2
C13—P1—Cu1	117.87 (12)	C16—C17—C18	120.1 (4)
C25—O2—C26	116.7 (3)	C16—C17—H17	120.0
C19—N1—N2	119.7 (3)	C18—C17—H17	120.0
C19—N1—H1	120.1	C17—C18—C13	120.9 (3)
N2—N1—H1	120.1	C17—C18—H18	119.5
C20—N2—N1	114.6 (3)	C13—C18—H18	119.5
C19—N3—H3A	120.0	N3—C19—N1	118.8 (3)
C19—N3—H3B	120.0	N3—C19—S1	120.9 (3)
H3A—N3—H3B	120.0	N1—C19—S1	120.3 (3)
C2—C1—C6	119.4 (3)	N2—C20—C21	121.1 (3)
C2—C1—P1	123.3 (2)	N2—C20—H20	119.5
C6—C1—P1	117.1 (3)	C21—C20—H20	119.5
C3—C2—C1	120.5 (3)	C28—C21—C22	119.2 (3)
C3—C2—H2	119.8	C28—C21—C20	122.0 (3)
C1—C2—H2	119.8	C22—C21—C20	118.8 (3)
C4—C3—C2	119.9 (4)	C23—C22—C21	121.0 (3)
C4—C3—H3	120.0	C23—C22—H22	119.5
C2—C3—H3	120.0	C21—C22—H22	119.5
C5—C4—C3	120.1 (4)	C22—C23—C24	119.9 (3)
C5—C4—H4	119.9	C22—C23—H23	120.1
C3—C4—H4	119.9	C24—C23—H23	120.1
C4—C5—C6	120.8 (3)	C23—C24—C27	119.3 (3)
C4—C5—H5	119.6	C23—C24—C25	119.3 (3)
C6—C5—H5	119.6	C27—C24—C25	121.4 (3)
C5—C6—C1	119.2 (3)	O1—C25—O2	123.5 (3)
C5—C6—H6	120.4	O1—C25—C24	125.2 (3)
C1—C6—H6	120.4	O2—C25—C24	111.3 (3)
C8—C7—C12	118.4 (3)	O2—C26—H26A	109.5
C8—C7—P1	124.6 (3)	O2—C26—H26B	109.5
C12—C7—P1	117.0 (2)	H26A—C26—H26B	109.5
C9—C8—C7	120.1 (3)	O2—C26—H26C	109.5
C9—C8—H8	120.0	H26A—C26—H26C	109.5
C7—C8—H8	120.0	H26B—C26—H26C	109.5
C10—C9—C8	120.9 (3)	C28—C27—C24	120.3 (4)
C10—C9—H9	119.6	C28—C27—H27	119.8
C8—C9—H9	119.6	C24—C27—H27	119.8
C9—C10—C11	119.9 (3)	C27—C28—C21	120.3 (3)
C9—C10—H10	120.1	C27—C28—H28	119.9
C11—C10—H10	120.1	C21—C28—H28	119.9

Symmetry code: (i) −x+1, −y+2, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3B···O1ⁱⁱ	0.86	2.17	2.963 (5)	154

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

Experimental details

Crystal data
Chemical formula	[Cu₂I₂(C₁₀H₁₁N₃O₂S)₂(C₁₈H₁₅P)₂]
M_r	1380.02
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	9.6319 (16), 11.945 (2), 13.581 (4)
α, β, γ (°)	108.627 (4), 101.655 (4), 105.044 (3)
V (Å³)	1359.0 (5)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	2.11
Crystal size (mm)	0.18 × 0.11 × 0.09

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.757, 0.827
No. of measured, independent and observed [I > 2σ(I)] reflections	22347, 5922, 4560
R_int	0.065
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.073, 1.02
No. of reflections	5922
No. of parameters	335
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.56, −0.82

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), 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
N3—H3B···O1ⁱ	0.860	2.165	2.963 (5)	154.09

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

Acknowledgements

PG thanks the Department of Science and Technology, India, for research grant SR/FT/CS-057/2009. SM thanks the CSIR, India, for his PhD fellowship. VN thanks the DST for an INSPIRE fellowship.

References

Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Dutta, S., Basuli, F., Castineiras, A., Peng, S. M., Lee, G. H. & Bhattacharya, S. (2008). Eur. J. Inorg. Chem. pp. 4538–4546. Web of Science CSD CrossRef Google Scholar
Lobana, T. S., Khanna, S., Hundal, G., Kaur, P., Thakur, B., Attri, S. & Butcher, R. J. (2009). Polyhedron, 28, 1583–1593. Web of Science CSD CrossRef CAS Google Scholar
Quiroga, A. G., Perez, J. M., Solera, I. L., Masaguer, J. R., Luque, A., Raman, P., Edwards, A., Alonso, C. & Ranninger, C. N. (1998). J. Med. Chem. 41, 1399–1408. Web of Science CSD CrossRef CAS PubMed Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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