Redetermination of catena-poly[[chlorido­(thio­urea-κS)copper(I)]-μ-thio­urea-κ2S:S] at 100 K

Zouihri, H.

doi:10.1107/S1600536812004448

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 3| March 2012| Pages m260-m261

doi:10.1107/S1600536812004448

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Redetermination of catena-poly[[chlorido(thiourea-κS)copper(I)]-μ-thiourea-κ²S:S] at 100 K

Hafid Zouihri ^a ^*

^aLaboratoire Privé de Cristallographie (LPC), Kénitra, Morocco.
^*Correspondence e-mail: hafid.zouihri@gmail.com

(Received 8 January 2012; accepted 2 February 2012; online 10 February 2012)

The structure of the polymeric title compound, [CuCl(CH₄N₂S)₂]_n, has been redetermined to modern standards of precision with anisotropic refinement and location of the H atoms. The previous structure report [Spofford & Amma (1970 ). Acta Cryst. B26, 1474–1483] is generally confirmed to higher precision [typical Cu—S bond length s.u. values = 0.005 (old) and 0.001 Å (new)]. The asymmetric unit contains two formula units, with both Cu^I atoms coordinated by one terminal S atom and two bridging S atoms of thiourea ligands. This connectivity leads to polymeric [100] chains in the crystal. If very long contacts to nearby chloride ions [2.8687 (9) and 3.1394 (12) Å] are considered to be bonding, then very distorted CuS₃Cl tetrahedral coordination polyhedra arise. The crystal structure is consolidated by weak intra- and inter-chain N—H⋯S and N—H⋯Cl hydrogen bonds.

Related literature

For the structure of a related thiourea salt, see: Zouihri (2012 ). For the previous structure determination of the title compound, see: Spofford & Amma (1970).

Experimental

Crystal data

[CuCl(CH₄N₂S)₂]
M_r = 251.24
Monoclinic, P 2₁ /c
a = 5.8043 (2) Å
b = 8.1292 (3) Å
c = 35.9657 (12) Å
β = 92.326 (2)°
V = 1695.62 (10) Å³
Z = 8
Mo Kα radiation
μ = 3.32 mm⁻¹
T = 100 K
0.45 × 0.18 × 0.07 mm

Data collection

Bruker APEXII CCD detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.493, T_max = 0.793
18106 measured reflections
4089 independent reflections
3372 reflections with I > 2σ(I)
R_int = 0.040

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.081
S = 1.15
4089 reflections
245 parameters
16 restraints
All H-atom parameters refined
Δρ_max = 0.58 e Å⁻³
Δρ_min = −0.85 e Å⁻³

Table 1
Selected bond lengths (Å)

Cu1—S1	2.3091 (9)
Cu1—S2	2.2617 (10)
Cu1—S3	2.2728 (10)
Cu1—Cl2	3.1394 (12)
Cu2—S1ⁱ	2.3081 (9)
Cu2—S3	2.2747 (9)
Cu2—S4	2.2421 (9)
Cu2—Cl1	2.8687 (9)
Symmetry code: (i) x-1, y, z.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯Cl1ⁱⁱ	0.85 (3)	2.44 (3)	3.230 (3)	154 (4)
N1—H1B⋯S4ⁱⁱⁱ	0.87 (3)	2.55 (3)	3.404 (4)	171 (3)
N2—H2A⋯S2	0.87 (3)	2.54 (3)	3.379 (3)	164 (3)
N2—H2B⋯Cl1ⁱⁱ	0.86 (3)	2.56 (3)	3.344 (3)	153 (3)
N3—H3A⋯S1	0.87 (3)	2.65 (3)	3.488 (4)	164 (3)
N3—H3B⋯Cl2^iv	0.86 (4)	2.57 (4)	3.373 (4)	156 (4)
N4—H4A⋯Cl2^iv	0.85 (3)	2.49 (3)	3.309 (3)	161 (3)
N4—H4B⋯Cl2^v	0.84 (3)	2.55 (3)	3.340 (3)	157 (4)
N5—H5A⋯Cl2	0.86 (3)	2.35 (3)	3.197 (3)	167 (4)
N5—H5B⋯Cl2^vi	0.86 (3)	2.55 (4)	3.356 (3)	157 (3)
N6—H6A⋯Cl2ⁱ	0.87 (4)	2.66 (4)	3.323 (3)	134 (4)
N6—H6B⋯Cl1	0.86 (2)	2.44 (2)	3.296 (3)	174 (3)
N7—H7A⋯Cl1	0.85 (3)	2.61 (4)	3.343 (4)	145 (3)
N7—H7B⋯Cl1^vii	0.87 (4)	2.55 (4)	3.367 (4)	157 (3)
N8—H8A⋯Cl1^vii	0.86 (4)	2.54 (4)	3.326 (4)	152 (3)
N8—H8B⋯Cl1^viii	0.85 (3)	2.55 (3)	3.298 (4)	148 (4)
Symmetry codes: (i) x-1, y, z; (ii) x+1, y+1, z; (iii) x+1, y, z; (iv) -x+1, -y+1, -z; (v) -x, -y+1, -z; (vi) -x, -y, -z; (vii) $[-x-1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (viii) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2005 ); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812004448/hb6598sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812004448/hb6598Isup2.hkl

checkCIF report

Comment top

In a former paper, we reported the crystal structure of (Diaminomethylidene)sulfonium chloride-thiourea (3/2) [Zouihri, 2012]. In this paper, we report the synthesis and the structure of the title compound. It was previously described by Spofford & Amma (1970).

The asymmetric unit of the title compound is shown in Fig. 1. The Cu^I ions have distorted tetrahedral coordination geometries formed by two bridging thiourea ligands, one terminal thiourea ligand and one chloride ion (Cu—S and Cu—Cl distances in the range of 2.2618 (10) Å to 3.1392 (12) Å) generating parallel one-dimensional polymeric chains propagating in the a axis direction.

In the crystal structure, there are two different types of hydrogen bonds (Table 1, Fig. 2). Intra-chain N—H···S and N—H···Cl interactions appear to influence the conformation of the helical chains while inter-chain N—H···S and N—H···Cl interactions crosslink the chains.

Related literature top

For the structure of a related thiourea salt, see: Zouihri (2012). For the previous structure determination of the title compound, see: Spofford & Amma (1970).

Experimental top

2 mmol of CuCl₂ and 1 mmol of (Diaminomethylidene)sulfonium chloride-thiourea (3/2) [Zouihri, 2012] in 5 ml of ethanol were refluxed for 1 h, forming a colorless solution. The solution was allowed to evaporate slowly and colourless prisms were obtained after several days.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. Molecular view of the title compound showing displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. Projection of the title compound along the a axis, H-bonds are represented by dashed lines.

catena-poly[[chlorido(thiourea-κS)copper(I)]-µ-thiourea- κ²S:S] top

Crystal data top

[CuCl(CH₄N₂S)₂]	F(000) = 1008
M_r = 251.24	D_x = 1.968 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 368 reflections
a = 5.8043 (2) Å	θ = 1.7–27.2°
b = 8.1292 (3) Å	µ = 3.32 mm⁻¹
c = 35.9657 (12) Å	T = 100 K
β = 92.326 (2)°	Prism, colourless
V = 1695.62 (10) Å³	0.45 × 0.18 × 0.07 mm
Z = 8

Data collection top

Bruker APEXII CCD detector diffractometer	4089 independent reflections
Radiation source: fine-focus sealed tube	3372 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.040
ω and ϕ scans	θ_max = 28.0°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→7
T_min = 0.493, T_max = 0.793	k = −10→10
18106 measured reflections	l = −47→33

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) = 0.081	All H-atom parameters refined
S = 1.15	w = 1/[σ²(F_o²) + (0.0226P)² + 3.6977P] where P = (F_o² + 2F_c²)/3
4089 reflections	(Δ/σ)_max = 0.001
245 parameters	Δρ_max = 0.58 e Å⁻³
16 restraints	Δρ_min = −0.85 e Å⁻³

Crystal data top

[CuCl(CH₄N₂S)₂]	V = 1695.62 (10) Å³
M_r = 251.24	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 5.8043 (2) Å	µ = 3.32 mm⁻¹
b = 8.1292 (3) Å	T = 100 K
c = 35.9657 (12) Å	0.45 × 0.18 × 0.07 mm
β = 92.326 (2)°

Data collection top

Bruker APEXII CCD detector diffractometer	4089 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3372 reflections with I > 2σ(I)
T_min = 0.493, T_max = 0.793	R_int = 0.040
18106 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	16 restraints
wR(F²) = 0.081	All H-atom parameters refined
S = 1.15	Δρ_max = 0.58 e Å⁻³
4089 reflections	Δρ_min = −0.85 e Å⁻³
245 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	0.20578 (8)	0.31958 (6)	0.100266 (15)	0.02808 (13)
Cu2	−0.13231 (8)	0.24956 (6)	0.157138 (12)	0.02293 (12)
Cl1	−0.45164 (14)	0.01524 (10)	0.18514 (2)	0.01749 (17)
Cl2	0.35733 (14)	0.18063 (12)	0.02357 (3)	0.0253 (2)
S3	0.05347 (13)	0.07669 (10)	0.11866 (2)	0.01369 (17)
S4	0.06418 (14)	0.35188 (12)	0.20688 (3)	0.0207 (2)
S2	0.02223 (14)	0.52774 (12)	0.06966 (3)	0.01974 (19)
S1	0.55003 (14)	0.38438 (11)	0.13126 (3)	0.01895 (19)
C4	−0.1303 (6)	0.3857 (4)	0.24079 (10)	0.0203 (8)
C3	−0.1615 (5)	0.0262 (4)	0.08459 (9)	0.0148 (7)
C1	0.5411 (6)	0.5852 (4)	0.14784 (10)	0.0183 (7)
C2	0.2234 (6)	0.6102 (4)	0.04098 (10)	0.0179 (7)
N3	0.4489 (5)	0.5983 (5)	0.04812 (10)	0.0268 (8)
N1	0.7193 (6)	0.6469 (4)	0.16698 (10)	0.0277 (8)
N7	−0.3535 (5)	0.3549 (5)	0.23575 (10)	0.0298 (8)
N2	0.3566 (5)	0.6769 (4)	0.14099 (9)	0.0224 (7)
N4	0.1543 (5)	0.6897 (5)	0.01073 (9)	0.0259 (7)
N6	−0.3721 (5)	−0.0059 (4)	0.09504 (9)	0.0227 (7)
N5	−0.1090 (5)	0.0156 (4)	0.04974 (8)	0.0218 (7)
N8	−0.0560 (6)	0.4419 (5)	0.27368 (10)	0.0295 (8)
H5A	0.026 (4)	0.043 (5)	0.0426 (12)	0.037 (13)*
H6A	−0.482 (6)	−0.015 (6)	0.0781 (11)	0.049 (15)*
H7A	−0.398 (7)	0.304 (5)	0.2160 (8)	0.034 (13)*
H8A	−0.148 (6)	0.478 (6)	0.2898 (10)	0.040 (14)*
H3A	0.500 (7)	0.538 (4)	0.0666 (8)	0.023 (11)*
H4A	0.258 (5)	0.731 (5)	−0.0024 (10)	0.024 (11)*
H5B	−0.207 (6)	−0.017 (5)	0.0328 (9)	0.028 (11)*
H6B	−0.401 (7)	0.005 (5)	0.1181 (6)	0.027 (12)*
H7B	−0.443 (7)	0.391 (6)	0.2526 (10)	0.043 (14)*
H8B	0.082 (4)	0.477 (6)	0.2753 (14)	0.048 (15)*
H2B	0.358 (7)	0.775 (3)	0.1496 (11)	0.025 (12)*
H1B	0.817 (6)	0.573 (4)	0.1748 (11)	0.025 (11)*
H4B	0.016 (4)	0.692 (5)	0.0030 (12)	0.030 (12)*
H3B	0.537 (7)	0.639 (6)	0.0320 (10)	0.041 (14)*
H2A	0.249 (5)	0.639 (5)	0.1260 (9)	0.026 (11)*
H1A	0.715 (8)	0.743 (3)	0.1764 (13)	0.044 (14)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0184 (2)	0.0208 (2)	0.0442 (3)	−0.00450 (19)	−0.0103 (2)	0.0088 (2)
Cu2	0.0198 (2)	0.0286 (3)	0.0199 (2)	0.00834 (19)	−0.00549 (18)	−0.0093 (2)
Cl1	0.0177 (4)	0.0183 (4)	0.0164 (4)	0.0011 (3)	0.0005 (3)	−0.0003 (3)
Cl2	0.0123 (4)	0.0327 (5)	0.0309 (5)	−0.0007 (4)	0.0013 (3)	0.0069 (4)
S3	0.0108 (3)	0.0163 (4)	0.0139 (4)	0.0007 (3)	−0.0005 (3)	−0.0006 (3)
S4	0.0119 (4)	0.0297 (5)	0.0202 (4)	0.0024 (3)	−0.0022 (3)	−0.0077 (4)
S2	0.0102 (4)	0.0267 (5)	0.0223 (5)	0.0015 (3)	0.0006 (3)	0.0057 (4)
S1	0.0160 (4)	0.0135 (4)	0.0266 (5)	0.0012 (3)	−0.0077 (4)	−0.0010 (3)
C4	0.0162 (16)	0.0191 (18)	0.0251 (19)	0.0030 (14)	−0.0043 (14)	−0.0062 (15)
C3	0.0121 (15)	0.0167 (17)	0.0156 (17)	−0.0031 (13)	−0.0002 (13)	−0.0031 (13)
C1	0.0169 (16)	0.0179 (18)	0.0200 (18)	−0.0008 (14)	0.0007 (14)	0.0027 (14)
C2	0.0138 (15)	0.0233 (19)	0.0166 (17)	0.0016 (14)	−0.0019 (13)	−0.0019 (14)
N3	0.0121 (14)	0.042 (2)	0.0262 (19)	−0.0001 (14)	0.0008 (13)	0.0125 (16)
N1	0.0277 (17)	0.0149 (17)	0.039 (2)	0.0035 (14)	−0.0143 (15)	−0.0072 (15)
N7	0.0121 (14)	0.051 (2)	0.0263 (19)	−0.0026 (15)	0.0018 (14)	−0.0180 (17)
N2	0.0181 (15)	0.0173 (16)	0.0314 (18)	0.0034 (13)	−0.0036 (13)	−0.0054 (15)
N4	0.0114 (14)	0.041 (2)	0.0249 (18)	−0.0017 (14)	−0.0019 (13)	0.0098 (15)
N6	0.0153 (14)	0.0362 (19)	0.0166 (16)	−0.0091 (14)	0.0006 (13)	−0.0030 (15)
N5	0.0152 (15)	0.0377 (19)	0.0123 (15)	−0.0063 (14)	−0.0001 (12)	−0.0044 (13)
N8	0.0185 (16)	0.046 (2)	0.0237 (18)	−0.0033 (16)	−0.0016 (14)	−0.0193 (16)

Geometric parameters (Å, º) top

Cu1—S1	2.3091 (9)	C1—N2	1.320 (4)
Cu1—S2	2.2617 (10)	C2—N4	1.314 (5)
Cu1—S3	2.2728 (10)	C2—N3	1.327 (4)
Cu1—Cl2	3.1394 (12)	N3—H3A	0.867 (19)
Cu2—S1ⁱ	2.3081 (9)	N3—H3B	0.853 (19)
Cu2—S3	2.2747 (9)	N1—H1B	0.862 (19)
Cu2—S4	2.2421 (9)	N1—H1A	0.855 (19)
Cu2—Cl1	2.8687 (9)	N7—H7A	0.854 (19)
Cu1—Cu2	2.9470 (7)	N7—H7B	0.867 (19)
S3—C3	1.761 (3)	N2—H2B	0.852 (19)
S4—C4	1.717 (4)	N2—H2A	0.867 (19)
S2—C2	1.725 (4)	N4—H4A	0.852 (19)
S1—C1	1.739 (4)	N4—H4B	0.837 (19)
S1—Cu2ⁱⁱ	2.3081 (9)	N6—H6A	0.866 (19)
C4—N8	1.324 (5)	N6—H6B	0.857 (19)
C4—N7	1.325 (4)	N5—H5A	0.862 (19)
C3—N5	1.305 (4)	N5—H5B	0.856 (19)
C3—N6	1.320 (4)	N8—H8A	0.856 (19)
C1—N1	1.319 (5)	N8—H8B	0.852 (19)

Cl2—Cu1—S1	103.79 (3)	N5—C3—S3	119.8 (2)
Cl2—Cu1—S2	89.13 (4)	N6—C3—S3	119.1 (3)
Cl2—Cu1—S3	93.98 (3)	N1—C1—N2	119.7 (3)
S1—Cu1—S2	116.46 (4)	N1—C1—S1	120.1 (3)
S1—Cu1—S3	113.38 (4)	N2—C1—S1	120.1 (3)
S2—Cu1—S3	127.63 (4)	N4—C2—N3	117.5 (3)
Cl1—Cu2—S3	97.61 (3)	N4—C2—S2	119.7 (3)
Cl1—Cu2—S4	106.33 (3)	N3—C2—S2	122.8 (3)
Cl1—Cu2—S1ⁱ	86.56 (3)	C2—N3—H3A	120 (3)
S2—Cu1—S3	127.63 (4)	C2—N3—H3B	117 (3)
S2—Cu1—S1	116.46 (4)	H3A—N3—H3B	123 (4)
S3—Cu1—S1	113.38 (4)	C1—N1—H1B	113 (3)
S2—Cu1—Cu2	99.70 (3)	C1—N1—H1A	122 (3)
S3—Cu1—Cu2	49.63 (2)	H1B—N1—H1A	122 (4)
S1—Cu1—Cu2	107.25 (3)	C4—N7—H7A	118 (3)
S4—Cu2—S3	118.44 (3)	C4—N7—H7B	117 (3)
S4—Cu2—S1ⁱ	121.18 (4)	H7A—N7—H7B	125 (4)
S3—Cu2—S1ⁱ	116.02 (4)	C1—N2—H2B	118 (3)
S4—Cu2—Cu1	98.66 (3)	C1—N2—H2A	118 (3)
S3—Cu2—Cu1	49.58 (3)	H2B—N2—H2A	124 (4)
S1ⁱ—Cu2—Cu1	99.90 (3)	C2—N4—H4A	117 (3)
C3—S3—Cu1	105.83 (12)	C2—N4—H4B	123 (3)
C3—S3—Cu2	103.14 (11)	H4A—N4—H4B	120 (4)
Cu1—S3—Cu2	80.79 (3)	C3—N6—H6A	119 (3)
C4—S4—Cu2	107.36 (12)	C3—N6—H6B	118 (3)
C2—S2—Cu1	105.36 (12)	H6A—N6—H6B	122 (4)
C1—S1—Cu2ⁱⁱ	110.00 (12)	C3—N5—H5A	121 (3)
C1—S1—Cu1	110.01 (12)	C3—N5—H5B	122 (3)
Cu2ⁱⁱ—S1—Cu1	138.40 (4)	H5A—N5—H5B	117 (4)
N8—C4—N7	117.9 (4)	C4—N8—H8A	122 (3)
N8—C4—S4	119.4 (3)	C4—N8—H8B	117 (3)
N7—C4—S4	122.7 (3)	H8A—N8—H8B	117 (5)
N5—C3—N6	121.0 (3)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cl1ⁱⁱⁱ	0.85 (3)	2.44 (3)	3.230 (3)	154 (4)
N1—H1B···S4ⁱⁱ	0.87 (3)	2.55 (3)	3.404 (4)	171 (3)
N2—H2A···S2	0.87 (3)	2.54 (3)	3.379 (3)	164 (3)
N2—H2B···Cl1ⁱⁱⁱ	0.86 (3)	2.56 (3)	3.344 (3)	153 (3)
N3—H3A···S1	0.87 (3)	2.65 (3)	3.488 (4)	164 (3)
N3—H3B···Cl2^iv	0.86 (4)	2.57 (4)	3.373 (4)	156 (4)
N4—H4A···Cl2^iv	0.85 (3)	2.49 (3)	3.309 (3)	161 (3)
N4—H4B···Cl2^v	0.84 (3)	2.55 (3)	3.340 (3)	157 (4)
N5—H5A···Cl2	0.86 (3)	2.35 (3)	3.197 (3)	167 (4)
N5—H5B···Cl2^vi	0.86 (3)	2.55 (4)	3.356 (3)	157 (3)
N6—H6A···Cl2ⁱ	0.87 (4)	2.66 (4)	3.323 (3)	134 (4)
N6—H6B···Cl1	0.86 (2)	2.44 (2)	3.296 (3)	174 (3)
N7—H7A···Cl1	0.85 (3)	2.61 (4)	3.343 (4)	145 (3)
N7—H7B···Cl1^vii	0.87 (4)	2.55 (4)	3.367 (4)	157 (3)
N8—H8A···Cl1^vii	0.86 (4)	2.54 (4)	3.326 (4)	152 (3)
N8—H8B···Cl1^viii	0.85 (3)	2.55 (3)	3.298 (4)	148 (4)

Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z; (iii) x+1, y+1, z; (iv) −x+1, −y+1, −z; (v) −x, −y+1, −z; (vi) −x, −y, −z; (vii) −x−1, y+1/2, −z+1/2; (viii) −x, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	[CuCl(CH₄N₂S)₂]
M_r	251.24
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	5.8043 (2), 8.1292 (3), 35.9657 (12)
β (°)	92.326 (2)
V (Å³)	1695.62 (10)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	3.32
Crystal size (mm)	0.45 × 0.18 × 0.07

Data collection
Diffractometer	Bruker APEXII CCD detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.493, 0.793
No. of measured, independent and observed [I > 2σ(I)] reflections	18106, 4089, 3372
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.661

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.081, 1.15
No. of reflections	4089
No. of parameters	245
No. of restraints	16
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.58, −0.85

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009), publCIF (Westrip, 2010).

Selected bond lengths (Å) top

Cu1—S1	2.3091 (9)	Cu2—S1ⁱ	2.3081 (9)
Cu1—S2	2.2617 (10)	Cu2—S3	2.2747 (9)
Cu1—S3	2.2728 (10)	Cu2—S4	2.2421 (9)
Cu1—Cl2	3.1394 (12)	Cu2—Cl1	2.8687 (9)

Symmetry code: (i) x−1, y, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cl1ⁱⁱ	0.85 (3)	2.44 (3)	3.230 (3)	154 (4)
N1—H1B···S4ⁱⁱⁱ	0.87 (3)	2.55 (3)	3.404 (4)	171 (3)
N2—H2A···S2	0.87 (3)	2.54 (3)	3.379 (3)	164 (3)
N2—H2B···Cl1ⁱⁱ	0.86 (3)	2.56 (3)	3.344 (3)	153 (3)
N3—H3A···S1	0.87 (3)	2.65 (3)	3.488 (4)	164 (3)
N3—H3B···Cl2^iv	0.86 (4)	2.57 (4)	3.373 (4)	156 (4)
N4—H4A···Cl2^iv	0.85 (3)	2.49 (3)	3.309 (3)	161 (3)
N4—H4B···Cl2^v	0.84 (3)	2.55 (3)	3.340 (3)	157 (4)
N5—H5A···Cl2	0.86 (3)	2.35 (3)	3.197 (3)	167 (4)
N5—H5B···Cl2^vi	0.86 (3)	2.55 (4)	3.356 (3)	157 (3)
N6—H6A···Cl2ⁱ	0.87 (4)	2.66 (4)	3.323 (3)	134 (4)
N6—H6B···Cl1	0.86 (2)	2.44 (2)	3.296 (3)	174 (3)
N7—H7A···Cl1	0.85 (3)	2.61 (4)	3.343 (4)	145 (3)
N7—H7B···Cl1^vii	0.87 (4)	2.55 (4)	3.367 (4)	157 (3)
N8—H8A···Cl1^vii	0.86 (4)	2.54 (4)	3.326 (4)	152 (3)
N8—H8B···Cl1^viii	0.85 (3)	2.55 (3)	3.298 (4)	148 (4)

Symmetry codes: (i) x−1, y, z; (ii) x+1, y+1, z; (iii) x+1, y, z; (iv) −x+1, −y+1, −z; (v) −x, −y+1, −z; (vi) −x, −y, −z; (vii) −x−1, y+1/2, −z+1/2; (viii) −x, y+1/2, −z+1/2.

Acknowledgements

The author thanks the Unit of Support for Technical and Scientific Research (UATRS, CNRST) for the X-ray measurements.

References

Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. 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
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
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Zouihri, H. (2012). Acta Cryst. E68, o257. Web of Science CSD CrossRef IUCr Journals Google Scholar

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