Bis­(N,N′-diphenyl­thio­urea)iodido­copper(I) monohydrate

Jia, L.; Kong, L.; Li, D.

doi:10.1107/S1600536808007861

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 6| June 2008| Page m763

doi:10.1107/S1600536808007861

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Bis(N,N′-diphenylthiourea)iodidocopper(I) monohydrate

Li Jia,^a Lingqian Kong ^b and Dacheng Li ^b ^*

^aLiaocheng Vocational and Technical College, Liaocheng, Shandong 252000, People's Republic of China, ^bDongchang College of Liaocheng University, Liaocheng, Shandong 252000, People's Republic of China, and ^cSchool of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China
^*Correspondence e-mail: lidacheng62@lcu.edu.cn

(Received 18 March 2008; accepted 22 March 2008; online 3 May 2008)

In the title compound, [CuI(C₁₃H₁₂N₂S)₂]·H₂O, each Cu(I) ion is coordinated by two S atoms [Cu—S 2.2282 (16), 2.2377 (15) Å] from two N,N′-diphenylthiourea ligands and one iodide ion [Cu—I 2.5170 (11) Å] in a trigonal planar geometry. The uncoordinated water molecules are involved in N—H⋯O hydrogen-bonding [N⋯O 2.947 (5), 3.055 (5) Å], which link the molecules into chains extended in the [101] direction. These chains are further paired by weak intermolecular O—H⋯S hydrogen bonds [O⋯S 3.490 (4) Å].

Related literature

For geometrical parameters in related crystal structures, see: Lobana et al. (2006 ).

Experimental

Crystal data

[CuI(C₁₃H₁₂N₂S)₂]·H₂O
M_r = 665.07
Triclinic, $[P \overline 1]$
a = 9.700 (4) Å
b = 12.490 (5) Å
c = 12.935 (5) Å
α = 91.489 (5)°
β = 108.110 (5)°
γ = 110.950 (5)°
V = 1374.4 (9) Å³
Z = 2
Mo Kα radiation
μ = 2.10 mm⁻¹
T = 298 (2) K
0.28 × 0.19 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.592, T_max = 0.704
7290 measured reflections
4804 independent reflections
2999 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.085
S = 0.87
4804 reflections
316 parameters
H-atom parameters constrained
Δρ_max = 0.57 e Å⁻³
Δρ_min = −0.45 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯I1	0.86	2.87	3.706 (4)	166
N2—H2⋯O1ⁱ	0.86	2.14	2.947 (5)	156
N3—H3⋯I1	0.86	2.82	3.666 (4)	168
N4—H4⋯O1ⁱⁱ	0.86	2.38	3.055 (5)	136
O1—H1B⋯S2ⁱⁱⁱ	0.85	2.64	3.490 (4)	179
Symmetry codes: (i) x-1, y, z; (ii) x, y, z+1; (iii) -x+1, -y, -z+1.

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); 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/S1600536808007861/cv2394sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808007861/cv2394Isup2.hkl

checkCIF report

Comment top

In this paper, we report the synthesis and the crystal structure of the title compound (I).

In (I) (Fig. 1), the Cu(I) ion is in a trigonal coordination environment formed by to two S atoms of two monodentate diphenylthiourea ligands and one iodine ion. The Cu-S [2.2282 (16), 2.2377 (15) Å] and Cu-I [2.5170 (11) Å] bond lengths agree well with those reported for the related compounds (Lobana et al., 2006).

The crystalline water molecules are involved in N—H···O hydrogen-bonding (Table 1), which link the molecules into chains extended in direction [101]. These chains are further paired (Fig. 2) by the weak intermolecular O—H···S hydrogen bonds (Table 1).

Related literature top

For geometrical parameters in related crystal structures, see: Lobana et al. (2006).

Experimental top

CuI (0.19 g 1 mmol) and diphenylthiourea (0.46 g 2 mmol) in 10 ml acetonitrile,refluxed for 24 h, then a colourless solution formed. After filtration, the solution was allowed to evaporate slowly. Crystals suitable for X-ray diffraction were obtained after several days.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SMART (Siemens, 1996); 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), showing the atomic numbering and 40% probability displacement ellipsoids. H atoms omitted for clarity.
	Fig. 2. A portion of the crystal packing showing the paired hydrogen-bonded (dashed lines) chains. H atoms not involved in hydrogen-bonding are omitted for clarity.

Bis(N,N'-diphenylthiourea)iodidocopper(I) monohydrate top

Crystal data top

[CuI(C₁₃H₁₂N₂S)₂]·H₂O	Z = 2
M_r = 665.07	F(000) = 664
Triclinic, P1	D_x = 1.607 Mg m⁻³
a = 9.700 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.490 (5) Å	Cell parameters from 1949 reflections
c = 12.935 (5) Å	θ = 2.4–22.1°
α = 91.489 (5)°	µ = 2.10 mm⁻¹
β = 108.110 (5)°	T = 298 K
γ = 110.950 (5)°	Block, colourless
V = 1374.4 (9) Å³	0.28 × 0.19 × 0.18 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	4804 independent reflections
Radiation source: fine-focus sealed tube	2999 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
phi and ω scans	θ_max = 25.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
T_min = 0.592, T_max = 0.704	k = −14→14
7290 measured reflections	l = −15→9

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.085	H-atom parameters constrained
S = 0.87	w = 1/[σ²(F_o²) + (0.0329P)²] where P = (F_o² + 2F_c²)/3
4804 reflections	(Δ/σ)_max < 0.001
316 parameters	Δρ_max = 0.58 e Å⁻³
0 restraints	Δρ_min = −0.45 e Å⁻³

Crystal data top

[CuI(C₁₃H₁₂N₂S)₂]·H₂O	γ = 110.950 (5)°
M_r = 665.07	V = 1374.4 (9) Å³
Triclinic, P1	Z = 2
a = 9.700 (4) Å	Mo Kα radiation
b = 12.490 (5) Å	µ = 2.10 mm⁻¹
c = 12.935 (5) Å	T = 298 K
α = 91.489 (5)°	0.28 × 0.19 × 0.18 mm
β = 108.110 (5)°

Data collection top

Bruker SMART CCD area-detector diffractometer	4804 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2999 reflections with I > 2σ(I)
T_min = 0.592, T_max = 0.704	R_int = 0.031
7290 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.085	H-atom parameters constrained
S = 0.87	Δρ_max = 0.58 e Å⁻³
4804 reflections	Δρ_min = −0.45 e Å⁻³
316 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	0.05943 (7)	0.11385 (5)	0.77393 (5)	0.04630 (19)
I1	0.17712 (4)	0.33136 (3)	0.82406 (3)	0.05399 (14)
N1	−0.0381 (4)	0.2061 (3)	0.5295 (3)	0.0443 (11)
H1	0.0273	0.2349	0.5952	0.053*
N2	−0.2538 (4)	0.0540 (3)	0.4163 (3)	0.0436 (11)
H2	−0.2571	0.0987	0.3669	0.052*
N3	0.2680 (4)	0.1602 (3)	1.0425 (3)	0.0405 (10)
H3	0.2322	0.1966	0.9921	0.049*
N4	0.3157 (4)	−0.0053 (3)	1.0771 (3)	0.0406 (10)
H4	0.3845	0.0350	1.1385	0.049*
O1	0.6610 (4)	0.1414 (3)	0.2058 (3)	0.0619 (11)
H1A	0.6840	0.2105	0.1920	0.074*
H1B	0.7159	0.1107	0.1858	0.074*
S1	−0.12503 (15)	0.01325 (10)	0.61534 (11)	0.0466 (4)
S2	0.11547 (15)	−0.01538 (10)	0.87828 (11)	0.0474 (4)
C1	−0.1409 (5)	0.0964 (4)	0.5129 (4)	0.0347 (12)
C2	−0.0288 (6)	0.2790 (4)	0.4464 (4)	0.0423 (13)
C3	−0.1082 (7)	0.3512 (4)	0.4296 (5)	0.0613 (16)
H3A	−0.1706	0.3526	0.4711	0.074*
C4	−0.0948 (8)	0.4228 (5)	0.3497 (5)	0.073 (2)
H4A	−0.1478	0.4729	0.3384	0.088*
C5	−0.0044 (7)	0.4203 (5)	0.2876 (5)	0.0701 (19)
H5	0.0043	0.4687	0.2345	0.084*
C6	0.0738 (8)	0.3459 (6)	0.3040 (6)	0.085 (2)
H6	0.1342	0.3424	0.2615	0.102*
C7	0.0606 (6)	0.2770 (5)	0.3844 (5)	0.0645 (17)
H7	0.1145	0.2275	0.3966	0.077*
C8	−0.3704 (5)	−0.0610 (4)	0.3884 (4)	0.0379 (12)
C9	−0.5254 (6)	−0.0777 (4)	0.3680 (4)	0.0470 (14)
H9	−0.5529	−0.0142	0.3729	0.056*
C10	−0.6383 (6)	−0.1869 (5)	0.3406 (5)	0.0624 (17)
H10	−0.7425	−0.1977	0.3278	0.075*
C11	−0.5994 (7)	−0.2808 (5)	0.3318 (5)	0.0687 (18)
H11	−0.6772	−0.3553	0.3124	0.082*
C12	−0.4450 (8)	−0.2653 (5)	0.3517 (5)	0.0665 (18)
H12	−0.4180	−0.3290	0.3465	0.080*
C13	−0.3309 (6)	−0.1546 (4)	0.3791 (5)	0.0512 (14)
H13	−0.2267	−0.1435	0.3914	0.061*
C14	0.2398 (5)	0.0499 (4)	1.0080 (4)	0.0342 (12)
C15	0.3482 (5)	0.2268 (4)	1.1501 (5)	0.0412 (13)
C16	0.4300 (7)	0.3453 (4)	1.1573 (5)	0.0581 (16)
H16	0.4354	0.3778	1.0941	0.070*
C17	0.5030 (8)	0.4140 (5)	1.2591 (6)	0.081 (2)
H17	0.5568	0.4935	1.2646	0.097*
C18	0.4967 (7)	0.3661 (5)	1.3517 (6)	0.0724 (19)
H18	0.5469	0.4131	1.4201	0.087*
C19	0.4175 (6)	0.2495 (5)	1.3452 (5)	0.0553 (15)
H19	0.4151	0.2173	1.4090	0.066*
C20	0.3410 (6)	0.1801 (4)	1.2436 (4)	0.0444 (13)
H20	0.2844	0.1012	1.2388	0.053*
C21	0.2935 (6)	−0.1242 (4)	1.0585 (4)	0.0371 (12)
C22	0.4230 (6)	−0.1510 (4)	1.0756 (4)	0.0492 (14)
H22	0.5229	−0.0927	1.0974	0.059*
C23	0.4029 (7)	−0.2666 (5)	1.0598 (5)	0.0631 (17)
H23	0.4903	−0.2856	1.0711	0.076*
C24	0.2569 (8)	−0.3529 (5)	1.0281 (5)	0.0699 (18)
H24	0.2448	−0.4300	1.0170	0.084*
C25	0.1277 (7)	−0.3252 (5)	1.0125 (5)	0.0673 (18)
H25	0.0279	−0.3838	0.9910	0.081*
C26	0.1456 (6)	−0.2107 (4)	1.0286 (5)	0.0498 (14)
H26	0.0583	−0.1920	1.0193	0.060*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0492 (4)	0.0489 (4)	0.0387 (4)	0.0194 (3)	0.0111 (3)	0.0147 (3)
I1	0.0693 (3)	0.0439 (2)	0.0507 (3)	0.02398 (19)	0.0197 (2)	0.01702 (19)
N1	0.044 (2)	0.041 (2)	0.033 (3)	0.010 (2)	0.001 (2)	0.011 (2)
N2	0.043 (2)	0.040 (2)	0.039 (3)	0.013 (2)	0.005 (2)	0.013 (2)
N3	0.053 (3)	0.037 (2)	0.030 (3)	0.019 (2)	0.008 (2)	0.010 (2)
N4	0.048 (2)	0.035 (2)	0.028 (2)	0.015 (2)	0.001 (2)	0.001 (2)
O1	0.065 (2)	0.056 (2)	0.050 (3)	0.017 (2)	0.008 (2)	0.010 (2)
S1	0.0489 (8)	0.0414 (8)	0.0394 (8)	0.0117 (6)	0.0077 (7)	0.0152 (7)
S2	0.0557 (8)	0.0400 (7)	0.0360 (8)	0.0166 (7)	0.0037 (7)	0.0076 (7)
C1	0.037 (3)	0.035 (3)	0.033 (3)	0.015 (2)	0.012 (3)	0.008 (2)
C2	0.046 (3)	0.037 (3)	0.041 (3)	0.015 (3)	0.011 (3)	0.014 (3)
C3	0.080 (4)	0.057 (4)	0.058 (4)	0.036 (3)	0.028 (4)	0.014 (3)
C4	0.112 (5)	0.057 (4)	0.066 (5)	0.052 (4)	0.025 (4)	0.032 (4)
C5	0.092 (5)	0.050 (4)	0.058 (4)	0.018 (3)	0.021 (4)	0.029 (3)
C6	0.103 (5)	0.104 (5)	0.086 (6)	0.054 (5)	0.062 (5)	0.057 (5)
C7	0.074 (4)	0.077 (4)	0.070 (5)	0.046 (4)	0.039 (4)	0.044 (4)
C8	0.039 (3)	0.041 (3)	0.029 (3)	0.009 (2)	0.012 (3)	0.006 (2)
C9	0.042 (3)	0.056 (3)	0.041 (4)	0.020 (3)	0.011 (3)	0.007 (3)
C10	0.041 (3)	0.071 (4)	0.062 (4)	0.007 (3)	0.020 (3)	−0.006 (4)
C11	0.064 (4)	0.057 (4)	0.059 (4)	−0.005 (3)	0.020 (4)	−0.007 (3)
C12	0.086 (5)	0.044 (4)	0.070 (5)	0.026 (4)	0.028 (4)	−0.003 (3)
C13	0.052 (3)	0.052 (4)	0.052 (4)	0.020 (3)	0.022 (3)	0.001 (3)
C14	0.034 (3)	0.032 (3)	0.032 (3)	0.007 (2)	0.012 (2)	0.004 (2)
C15	0.043 (3)	0.035 (3)	0.047 (4)	0.015 (2)	0.018 (3)	0.006 (3)
C16	0.082 (4)	0.040 (3)	0.055 (4)	0.013 (3)	0.039 (4)	0.009 (3)
C17	0.097 (5)	0.039 (3)	0.090 (6)	−0.008 (3)	0.050 (5)	−0.015 (4)
C18	0.084 (5)	0.057 (4)	0.061 (5)	0.006 (4)	0.031 (4)	−0.017 (4)
C19	0.057 (4)	0.058 (4)	0.043 (4)	0.015 (3)	0.016 (3)	0.000 (3)
C20	0.047 (3)	0.039 (3)	0.045 (4)	0.011 (3)	0.018 (3)	0.006 (3)
C21	0.050 (3)	0.037 (3)	0.026 (3)	0.018 (3)	0.013 (3)	0.012 (2)
C22	0.049 (3)	0.057 (4)	0.045 (4)	0.023 (3)	0.017 (3)	0.014 (3)
C23	0.081 (5)	0.070 (4)	0.065 (5)	0.046 (4)	0.039 (4)	0.022 (4)
C24	0.098 (5)	0.045 (4)	0.069 (5)	0.038 (4)	0.019 (4)	0.007 (3)
C25	0.064 (4)	0.043 (4)	0.077 (5)	0.009 (3)	0.013 (4)	0.017 (3)
C26	0.050 (3)	0.046 (3)	0.058 (4)	0.022 (3)	0.019 (3)	0.016 (3)

Geometric parameters (Å, º) top

Cu1—S1	2.2282 (16)	C9—C10	1.360 (7)
Cu1—S2	2.2377 (15)	C9—H9	0.9300
Cu1—I1	2.5170 (11)	C10—C11	1.367 (7)
N1—C1	1.338 (5)	C10—H10	0.9300
N1—C2	1.431 (6)	C11—C12	1.377 (7)
N1—H1	0.8600	C11—H11	0.9300
N2—C1	1.320 (6)	C12—C13	1.378 (7)
N2—C8	1.425 (5)	C12—H12	0.9300
N2—H2	0.8600	C13—H13	0.9300
N3—C14	1.340 (5)	C15—C20	1.367 (7)
N3—C15	1.427 (6)	C15—C16	1.392 (7)
N3—H3	0.8600	C16—C17	1.378 (8)
N4—C14	1.343 (5)	C16—H16	0.9300
N4—C21	1.424 (5)	C17—C18	1.362 (8)
N4—H4	0.8600	C17—H17	0.9300
O1—H1A	0.8500	C18—C19	1.367 (7)
O1—H1B	0.8500	C18—H18	0.9300
S1—C1	1.708 (5)	C19—C20	1.380 (7)
S2—C14	1.703 (5)	C19—H19	0.9300
C2—C7	1.358 (7)	C20—H20	0.9300
C2—C3	1.363 (6)	C21—C22	1.368 (6)
C3—C4	1.389 (7)	C21—C26	1.379 (6)
C3—H3A	0.9300	C22—C23	1.386 (7)
C4—C5	1.368 (8)	C22—H22	0.9300
C4—H4A	0.9300	C23—C24	1.364 (7)
C5—C6	1.377 (8)	C23—H23	0.9300
C5—H5	0.9300	C24—C25	1.373 (7)
C6—C7	1.375 (7)	C24—H24	0.9300
C6—H6	0.9300	C25—C26	1.379 (7)
C7—H7	0.9300	C25—H25	0.9300
C8—C13	1.367 (6)	C26—H26	0.9300
C8—C9	1.378 (6)

S1—Cu1—S2	106.87 (6)	C10—C11—C12	120.0 (5)
S1—Cu1—I1	125.81 (4)	C10—C11—H11	120.0
S2—Cu1—I1	127.32 (5)	C12—C11—H11	120.0
C1—N1—C2	125.0 (4)	C11—C12—C13	119.5 (5)
C1—N1—H1	117.5	C11—C12—H12	120.2
C2—N1—H1	117.5	C13—C12—H12	120.2
C1—N2—C8	124.3 (4)	C8—C13—C12	120.2 (5)
C1—N2—H2	117.8	C8—C13—H13	119.9
C8—N2—H2	117.8	C12—C13—H13	119.9
C14—N3—C15	130.0 (4)	N3—C14—N4	118.1 (4)
C14—N3—H3	115.0	N3—C14—S2	120.2 (4)
C15—N3—H3	115.0	N4—C14—S2	121.6 (3)
C14—N4—C21	126.3 (4)	C20—C15—C16	119.8 (5)
C14—N4—H4	116.8	C20—C15—N3	122.9 (4)
C21—N4—H4	116.8	C16—C15—N3	117.3 (5)
H1A—O1—H1B	110.0	C17—C16—C15	119.3 (6)
C1—S1—Cu1	112.56 (17)	C17—C16—H16	120.3
C14—S2—Cu1	111.44 (16)	C15—C16—H16	120.3
N2—C1—N1	118.9 (4)	C18—C17—C16	120.2 (5)
N2—C1—S1	120.9 (4)	C18—C17—H17	119.9
N1—C1—S1	120.3 (4)	C16—C17—H17	119.9
C7—C2—C3	119.7 (5)	C17—C18—C19	120.7 (6)
C7—C2—N1	119.9 (4)	C17—C18—H18	119.6
C3—C2—N1	120.4 (5)	C19—C18—H18	119.6
C2—C3—C4	119.3 (6)	C18—C19—C20	119.6 (6)
C2—C3—H3A	120.4	C18—C19—H19	120.2
C4—C3—H3A	120.4	C20—C19—H19	120.2
C5—C4—C3	120.7 (5)	C15—C20—C19	120.3 (5)
C5—C4—H4A	119.7	C15—C20—H20	119.9
C3—C4—H4A	119.7	C19—C20—H20	119.9
C4—C5—C6	119.8 (6)	C22—C21—C26	120.6 (5)
C4—C5—H5	120.1	C22—C21—N4	118.5 (4)
C6—C5—H5	120.1	C26—C21—N4	120.9 (4)
C7—C6—C5	118.7 (6)	C21—C22—C23	119.0 (5)
C7—C6—H6	120.7	C21—C22—H22	120.5
C5—C6—H6	120.7	C23—C22—H22	120.5
C2—C7—C6	121.9 (5)	C24—C23—C22	120.9 (5)
C2—C7—H7	119.0	C24—C23—H23	119.5
C6—C7—H7	119.0	C22—C23—H23	119.5
C13—C8—C9	119.7 (5)	C23—C24—C25	119.7 (5)
C13—C8—N2	120.8 (4)	C23—C24—H24	120.2
C9—C8—N2	119.5 (4)	C25—C24—H24	120.2
C10—C9—C8	120.2 (5)	C24—C25—C26	120.1 (5)
C10—C9—H9	119.9	C24—C25—H25	119.9
C8—C9—H9	119.9	C26—C25—H25	119.9
C9—C10—C11	120.4 (5)	C21—C26—C25	119.6 (5)
C9—C10—H10	119.8	C21—C26—H26	120.2
C11—C10—H10	119.8	C25—C26—H26	120.2

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···I1	0.86	2.87	3.706 (4)	166
N2—H2···O1ⁱ	0.86	2.14	2.947 (5)	156
N3—H3···I1	0.86	2.82	3.666 (4)	168
N4—H4···O1ⁱⁱ	0.86	2.38	3.055 (5)	136
O1—H1B···S2ⁱⁱⁱ	0.85	2.64	3.490 (4)	179

Symmetry codes: (i) x−1, y, z; (ii) x, y, z+1; (iii) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formula	[CuI(C₁₃H₁₂N₂S)₂]·H₂O
M_r	665.07
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	9.700 (4), 12.490 (5), 12.935 (5)
α, β, γ (°)	91.489 (5), 108.110 (5), 110.950 (5)
V (Å³)	1374.4 (9)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.10
Crystal size (mm)	0.28 × 0.19 × 0.18

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.592, 0.704
No. of measured, independent and observed [I > 2σ(I)] reflections	7290, 4804, 2999
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.085, 0.87
No. of reflections	4804
No. of parameters	316
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.58, −0.45

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), 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···I1	0.86	2.87	3.706 (4)	165.6
N2—H2···O1ⁱ	0.86	2.14	2.947 (5)	155.8
N3—H3···I1	0.86	2.82	3.666 (4)	168.3
N4—H4···O1ⁱⁱ	0.86	2.38	3.055 (5)	135.9
O1—H1B···S2ⁱⁱⁱ	0.85	2.64	3.490 (4)	179.4

Symmetry codes: (i) x−1, y, z; (ii) x, y, z+1; (iii) −x+1, −y, −z+1.

Acknowledgements

We thank the Natural Science Foundation of Liaocheng University (X051002) for support.

References

Lobana, T. S., Khanna, S., Butcher, R. J., Hunter, A. D. & Zeller, M. (2006). Polyhedron, 25, 2755–2763. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siemens (1996). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar