Bis[N,N-bis­(2-hydroxy­ethyl)dithio­carbamato-κ2S,S′]copper(II)

Hou, L.-F.; Zhong, Y.; Mei, Y.; Fan, J.

doi:10.1107/S160053680904999X

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page m1694

doi:10.1107/S160053680904999X

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Bis[N,N-bis(2-hydroxyethyl)dithiocarbamato-κ²S,S′]copper(II)

Lan-Feng Hou,^a Yun Zhong,^a ^* Yan Mei ^a and Jun Fan ^b

^aSchool of Basical Science, East China Jiaotong University, Nanchang 330013, People's Republic of China, and ^bSchool of Chemistry and Environment, South China Normal University, Guangzhou 510006, People's Republic of China
^*Correspondence e-mail: zhongyun1973@126.com

(Received 17 November 2009; accepted 20 November 2009; online 28 November 2009)

In the title compound, [Cu(C₅H₁₀NO₂S₂)₂], the Cu^II cation is chelated by two bis(2-hydroxyethyl)dithiocarbamate anions with a distorted square-planar coordination geometry. Intermolecular O—H⋯O hydrogen bonding is observed between the terminal hydroxy groups in the crystal structure.

Related literature

For the different oxidation state of Cu in copper–dithiocarbamate complexes, see: Cardell et al. (2006 ); Zhang et al. (2004 ); Jian et al. (1999 ); Hogarth et al. (2000 ). For the Cu—S bond distances in a related structure, see: Jian et al. (2003 ).

Experimental

Crystal data

[Cu(C₅H₁₀NO₂S₂)₂]
M_r = 424.06
Monoclinic, P 2₁ /c
a = 11.1088 (9) Å
b = 14.7047 (11) Å
c = 11.3401 (9) Å
β = 118.253 (1)°
V = 1631.7 (2) Å³
Z = 4
Mo Kα radiation
μ = 1.86 mm⁻¹
T = 298 K
0.35 × 0.35 × 0.30 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.562, T_max = 0.605
8158 measured reflections
2928 independent reflections
2652 reflections with I > 2σ(I)
R_int = 0.068

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.095
S = 1.03
2928 reflections
190 parameters
H-atom parameters constrained
Δρ_max = 1.74 e Å⁻³
Δρ_min = −0.56 e Å⁻³

Table 1
Selected bond lengths (Å)

Cu1—S1	2.3026 (8)
Cu1—S2	2.3201 (8)
Cu1—S3	2.3148 (8)
Cu1—S4	2.2999 (8)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O4ⁱ	0.82	1.86	2.654 (4)	162
O2—H2⋯O1ⁱⁱ	0.82	2.29	2.694 (3)	111
O3—H3⋯O2ⁱⁱⁱ	0.82	1.94	2.744 (3)	166
O4—H4⋯O3^iv	0.82	1.90	2.677 (3)	157
Symmetry codes: (i) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) -x, -y, -z+1; (iii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT (Bruker, 1999 ); data reduction: SAINT program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680904999X/xu2681sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680904999X/xu2681Isup2.hkl

checkCIF report

Comment top

Metal dithiocarbamate complexes have been extensively studied. Monomeric, dimeric, polymeric, two-dimensional and three-dimensional structures are all featured amongst these complexes. In copper dithiocarbamate complexes, the copper oxidation states I–III have been accessible (Cardell et al., 2006; Zhang et al., 2004; Jian et al., 1999; Hogarth et al., 2000) because dithiocarbamates have capability to stabilize transition metals in a wide range of oxidation states. The title complex (I), was synthesized and characterized by X-ray crystal structure analysis.

The title complex has a monomeric structure (shown as Fig.1). The copper atom, which has distorted square-planar geometry, was coordinated to four sulfur atoms of two 2-hydroxyethyldithiocarbamate ligands. The Cu—S distances ranged from 2.2999 (8) to 2.3201 (8) Å. This is consistent with the literature precedents (Jian, 2003). The interesting feature of this structure is the presence of hydrogen bonding between molecules, owing to the presence of hydrogen-bonding functionality in the N-bound residues. The structure can be thought of as being comprised of layers held together primarily by O—H–O interactions in the bc plane; see Table 2 for geometric parameters describing the hydrogen-bonding interactions. Successive layers stack parallel to the a direction, held together by O—H–O interactions.

Related literature top

For the different oxidation state of Cu in copper–dithiocarbamate complexes, see: Cardell et al. (2006); Zhang et al. (2004); Jian et al. (1999); Hogarth et al. (2000). For the Cu—S bond distances in a related structure, see: Jian et al. (2003).

Experimental top

NaOH(0.04 g, 1.0 mmol), NH(CH₂CH₂OH)₂ (0.105 g, 1.0 mmol) and CS₂ (0.092 g, 1.2 mmol) was stirred for 1 h in methanol (25 ml) at room temperature, to this solution, CuCl₂ (0.067 g, 0.5 mmol) was added. The mixture was stirred for 2 h at room temperature and the precipitate was filtered off. Black crystals were obtained from the slow evaporation of the filtrate.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound with 50% probability displacement ellipsoids for non-H atoms.

Bis[N,N-bis(2-hydroxyethyl)dithiocarbamato- κ²S,S']copper(II) top

Crystal data top

[Cu(C₅H₁₀NO₂S₂)₂]	F(000) = 876
M_r = 424.06	D_x = 1.726 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5620 reflections
a = 11.1088 (9) Å	θ = 2.5–28.1°
b = 14.7047 (11) Å	µ = 1.86 mm⁻¹
c = 11.3401 (9) Å	T = 298 K
β = 118.253 (1)°	Prism, black
V = 1631.7 (2) Å³	0.35 × 0.35 × 0.30 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	2928 independent reflections
Radiation source: fine-focus sealed tube	2652 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.068
ϕ and ω scans	θ_max = 25.3°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→9
T_min = 0.562, T_max = 0.605	k = −16→17
8158 measured reflections	l = −7→13

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.095	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0446P)² + 1.7228P] where P = (F_o² + 2F_c²)/3
2928 reflections	(Δ/σ)_max < 0.001
190 parameters	Δρ_max = 1.74 e Å⁻³
0 restraints	Δρ_min = −0.56 e Å⁻³

Crystal data top

[Cu(C₅H₁₀NO₂S₂)₂]	V = 1631.7 (2) Å³
M_r = 424.06	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.1088 (9) Å	µ = 1.86 mm⁻¹
b = 14.7047 (11) Å	T = 298 K
c = 11.3401 (9) Å	0.35 × 0.35 × 0.30 mm
β = 118.253 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2928 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2652 reflections with I > 2σ(I)
T_min = 0.562, T_max = 0.605	R_int = 0.068
8158 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.095	H-atom parameters constrained
S = 1.03	Δρ_max = 1.74 e Å⁻³
2928 reflections	Δρ_min = −0.56 e Å⁻³
190 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
C1	0.0521 (3)	−0.05853 (18)	0.2261 (3)	0.0192 (6)
C2	−0.1504 (3)	−0.0869 (2)	0.2496 (3)	0.0233 (6)
H2A	−0.1983	−0.1411	0.2531	0.028*
H2B	−0.2019	−0.0601	0.1614	0.028*
C3	−0.1424 (4)	−0.0196 (3)	0.3548 (4)	0.0406 (8)
H3A	−0.1207	−0.0520	0.4371	0.049*
H3B	−0.0697	0.0236	0.3735	0.049*
C4	0.0381 (3)	−0.20342 (18)	0.3257 (3)	0.0212 (6)
H4A	0.1013	−0.2229	0.2942	0.025*
H4B	−0.0383	−0.2454	0.2901	0.025*
C5	0.1091 (3)	−0.2093 (2)	0.4765 (3)	0.0227 (6)
H5A	0.0560	−0.1763	0.5100	0.027*
H5B	0.1130	−0.2725	0.5028	0.027*
C6	0.3436 (3)	0.17401 (18)	0.0766 (2)	0.0162 (5)
C7	0.5611 (3)	0.20374 (19)	0.0815 (3)	0.0190 (6)
H7A	0.5985	0.1702	0.1650	0.023*
H7B	0.6123	0.2600	0.0980	0.023*
C8	0.5805 (3)	0.1480 (2)	−0.0214 (3)	0.0255 (6)
H8A	0.6740	0.1264	0.0185	0.031*
H8B	0.5209	0.0953	−0.0462	0.031*
C9	0.3588 (3)	0.30637 (19)	−0.0457 (3)	0.0206 (6)
H9A	0.2618	0.3096	−0.0736	0.025*
H9B	0.3693	0.3001	−0.1255	0.025*
C10	0.4260 (3)	0.3936 (2)	0.0247 (3)	0.0307 (7)
H10A	0.5215	0.3927	0.0462	0.037*
H10B	0.3827	0.4445	−0.0347	0.037*
Cu1	0.18494 (3)	0.05408 (2)	0.13092 (3)	0.02051 (13)
N1	−0.0131 (2)	−0.11176 (16)	0.2714 (2)	0.0194 (5)
N2	0.4167 (2)	0.22570 (16)	0.0394 (2)	0.0166 (5)
O1	−0.2655 (3)	0.02700 (18)	0.3122 (3)	0.0447 (6)
H1	−0.3242	−0.0082	0.3092	0.067*
O2	0.2441 (2)	−0.17337 (15)	0.5363 (2)	0.0270 (5)
H2	0.2414	−0.1197	0.5156	0.040*
O3	0.5511 (2)	0.19925 (15)	−0.13961 (19)	0.0290 (5)
H3	0.6027	0.2431	−0.1195	0.044*
O4	0.4164 (3)	0.40549 (16)	0.1437 (2)	0.0457 (7)
H4	0.4534	0.3626	0.1944	0.069*
S1	0.20586 (7)	−0.08469 (5)	0.23294 (7)	0.02249 (18)
S2	−0.01496 (8)	0.04398 (5)	0.14746 (8)	0.02730 (19)
S3	0.17688 (7)	0.19631 (5)	0.03995 (7)	0.01979 (17)
S4	0.40396 (7)	0.07346 (5)	0.16331 (7)	0.02160 (18)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0173 (13)	0.0192 (14)	0.0184 (13)	−0.0016 (11)	0.0064 (11)	−0.0002 (10)
C2	0.0194 (14)	0.0258 (15)	0.0272 (15)	−0.0037 (12)	0.0130 (12)	−0.0013 (12)
C3	0.0315 (18)	0.051 (2)	0.047 (2)	−0.0082 (17)	0.0249 (16)	−0.0178 (18)
C4	0.0210 (14)	0.0159 (13)	0.0253 (14)	−0.0022 (11)	0.0097 (12)	0.0012 (11)
C5	0.0208 (14)	0.0214 (14)	0.0258 (15)	0.0013 (12)	0.0110 (12)	0.0039 (11)
C6	0.0163 (12)	0.0175 (13)	0.0151 (12)	0.0001 (11)	0.0076 (10)	−0.0040 (10)
C7	0.0144 (13)	0.0229 (14)	0.0202 (13)	−0.0002 (11)	0.0086 (11)	0.0004 (11)
C8	0.0250 (15)	0.0253 (15)	0.0311 (15)	0.0012 (13)	0.0173 (13)	−0.0021 (12)
C9	0.0172 (13)	0.0227 (14)	0.0203 (13)	0.0003 (11)	0.0077 (11)	0.0057 (11)
C10	0.0266 (16)	0.0206 (15)	0.0334 (17)	−0.0023 (13)	0.0047 (13)	0.0066 (13)
Cu1	0.0192 (2)	0.0191 (2)	0.0275 (2)	0.00087 (14)	0.01459 (16)	0.00434 (13)
N1	0.0161 (11)	0.0186 (11)	0.0226 (12)	−0.0017 (10)	0.0084 (9)	0.0018 (9)
N2	0.0146 (11)	0.0173 (11)	0.0182 (11)	−0.0005 (9)	0.0079 (9)	0.0009 (9)
O1	0.0341 (13)	0.0424 (14)	0.0581 (16)	0.0015 (12)	0.0223 (12)	−0.0075 (12)
O2	0.0191 (10)	0.0286 (11)	0.0287 (11)	0.0026 (9)	0.0076 (8)	0.0000 (9)
O3	0.0321 (12)	0.0350 (12)	0.0256 (10)	−0.0108 (10)	0.0183 (9)	−0.0059 (9)
O4	0.0601 (17)	0.0282 (12)	0.0299 (12)	0.0181 (12)	0.0058 (11)	−0.0052 (10)
S1	0.0161 (3)	0.0221 (4)	0.0296 (4)	0.0025 (3)	0.0111 (3)	0.0073 (3)
S2	0.0251 (4)	0.0220 (4)	0.0423 (4)	0.0070 (3)	0.0221 (3)	0.0120 (3)
S3	0.0157 (3)	0.0196 (3)	0.0263 (4)	0.0013 (3)	0.0118 (3)	0.0025 (3)
S4	0.0195 (3)	0.0189 (3)	0.0294 (4)	0.0034 (3)	0.0140 (3)	0.0062 (3)

Geometric parameters (Å, º) top

C1—N1	1.324 (4)	C7—C8	1.522 (4)
C1—S1	1.717 (3)	C7—H7A	0.9700
C1—S2	1.730 (3)	C7—H7B	0.9700
C2—N1	1.472 (4)	C8—O3	1.434 (4)
C2—C3	1.519 (4)	C8—H8A	0.9700
C2—H2A	0.9700	C8—H8B	0.9700
C2—H2B	0.9700	C9—N2	1.471 (3)
C3—O1	1.396 (4)	C9—C10	1.508 (4)
C3—H3A	0.9700	C9—H9A	0.9700
C3—H3B	0.9700	C9—H9B	0.9700
C4—N1	1.479 (3)	C10—O4	1.414 (4)
C4—C5	1.510 (4)	C10—H10A	0.9700
C4—H4A	0.9700	C10—H10B	0.9700
C4—H4B	0.9700	Cu1—S1	2.3026 (8)
C5—O2	1.423 (3)	Cu1—S2	2.3201 (8)
C5—H5A	0.9700	Cu1—S3	2.3148 (8)
C5—H5B	0.9700	Cu1—S4	2.2999 (8)
C6—N2	1.319 (4)	O1—H1	0.8200
C6—S4	1.726 (3)	O2—H2	0.8200
C6—S3	1.727 (3)	O3—H3	0.8200
C7—N2	1.477 (3)	O4—H4	0.8200

N1—C1—S1	124.4 (2)	O3—C8—H8A	109.1
N1—C1—S2	122.3 (2)	C7—C8—H8A	109.1
S1—C1—S2	113.23 (16)	O3—C8—H8B	109.1
N1—C2—C3	111.0 (2)	C7—C8—H8B	109.1
N1—C2—H2A	109.4	H8A—C8—H8B	107.8
C3—C2—H2A	109.4	N2—C9—C10	112.7 (2)
N1—C2—H2B	109.4	N2—C9—H9A	109.1
C3—C2—H2B	109.4	C10—C9—H9A	109.1
H2A—C2—H2B	108.0	N2—C9—H9B	109.1
O1—C3—C2	111.3 (3)	C10—C9—H9B	109.1
O1—C3—H3A	109.4	H9A—C9—H9B	107.8
C2—C3—H3A	109.4	O4—C10—C9	111.6 (3)
O1—C3—H3B	109.4	O4—C10—H10A	109.3
C2—C3—H3B	109.4	C9—C10—H10A	109.3
H3A—C3—H3B	108.0	O4—C10—H10B	109.3
N1—C4—C5	114.6 (2)	C9—C10—H10B	109.3
N1—C4—H4A	108.6	H10A—C10—H10B	108.0
C5—C4—H4A	108.6	S4—Cu1—S1	100.48 (3)
N1—C4—H4B	108.6	S4—Cu1—S3	76.94 (3)
C5—C4—H4B	108.6	S1—Cu1—S3	176.35 (3)
H4A—C4—H4B	107.6	S4—Cu1—S2	167.33 (3)
O2—C5—C4	112.7 (2)	S1—Cu1—S2	77.02 (3)
O2—C5—H5A	109.1	S3—Cu1—S2	104.91 (3)
C4—C5—H5A	109.1	C1—N1—C2	120.1 (2)
O2—C5—H5B	109.1	C1—N1—C4	121.8 (2)
C4—C5—H5B	109.1	C2—N1—C4	117.4 (2)
H5A—C5—H5B	107.8	C6—N2—C9	122.0 (2)
N2—C6—S4	123.0 (2)	C6—N2—C7	120.7 (2)
N2—C6—S3	124.5 (2)	C9—N2—C7	117.3 (2)
S4—C6—S3	112.51 (15)	C3—O1—H1	109.5
N2—C7—C8	113.3 (2)	C5—O2—H2	109.5
N2—C7—H7A	108.9	C8—O3—H3	109.5
C8—C7—H7A	108.9	C10—O4—H4	109.5
N2—C7—H7B	108.9	C1—S1—Cu1	85.25 (10)
C8—C7—H7B	108.9	C1—S2—Cu1	84.42 (10)
H7A—C7—H7B	107.7	C6—S3—Cu1	84.86 (9)
O3—C8—C7	112.5 (2)	C6—S4—Cu1	85.35 (9)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O4ⁱ	0.82	1.86	2.654 (4)	162
O2—H2···O1ⁱⁱ	0.82	2.29	2.694 (3)	111
O3—H3···O2ⁱⁱⁱ	0.82	1.94	2.744 (3)	166
O4—H4···O3^iv	0.82	1.90	2.677 (3)	157

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

Experimental details

Crystal data
Chemical formula	[Cu(C₅H₁₀NO₂S₂)₂]
M_r	424.06
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	11.1088 (9), 14.7047 (11), 11.3401 (9)
β (°)	118.253 (1)
V (Å³)	1631.7 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.86
Crystal size (mm)	0.35 × 0.35 × 0.30

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.562, 0.605
No. of measured, independent and observed [I > 2σ(I)] reflections	8158, 2928, 2652
R_int	0.068
(sin θ/λ)_max (Å⁻¹)	0.600

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.095, 1.03
No. of reflections	2928
No. of parameters	190
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.74, −0.56

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997).

Selected bond lengths (Å) top

Cu1—S1	2.3026 (8)	Cu1—S3	2.3148 (8)
Cu1—S2	2.3201 (8)	Cu1—S4	2.2999 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O4ⁱ	0.82	1.86	2.654 (4)	162.3
O2—H2···O1ⁱⁱ	0.82	2.29	2.694 (3)	110.8
O3—H3···O2ⁱⁱⁱ	0.82	1.94	2.744 (3)	165.5
O4—H4···O3^iv	0.82	1.90	2.677 (3)	157.4

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

Acknowledgements

This work was supported by the Natural Science Foundation of Jiangxi Province, China (2007GZH1573).

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