(Thio-cyanato-κN)bis-(thio-semicarbazide-κS)copper(I).

In the title complex, [Cu(CH(5)N(3)S)(2)(NCS)], the non-H part of the mol-ecule is strictly planar, lying on the mirror plane at y = 0.25. The Cu atom lies at the centre of a triangle formed by the coordination of three monodentate groups, viz. two thio-semicarbazide ligands and one NCS(-) anion. Weak inter-molecular N-H⋯S inter-actions generate a two-dimensional network.

Related literature

For related thio­semicarbazide metal complexes, see: Capacchi et al. (1968 ▶). For related literature, see: Chattopadhyay et al. (1991 ▶).

Experimental

Crystal data

[Cu(CH5N3S)2(NCS)]

M = 303.90

Orthorhombic,

a = 11.488 (2) Å

b = 6.6085 (12) Å

c = 14.650 (3) Å

V = 1112.2 (4) Å3

Z = 4

Mo Kα radiation

μ = 2.50 mm−1

T = 298 (2) K

0.38 × 0.27 × 0.24 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.44, T max = 0.55

5593 measured reflections

1077 independent reflections

947 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.080

S = 1.05

1077 reflections

86 parameters

H-atom parameters constrained

Δρmax = 0.67 e Å−3

Δρmin = −0.54 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); 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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808013068/bg2183sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808013068/bg2183Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Cu(CH5N3S)2(NCS)]	F(000) = 616
Mr = 303.90	Dx = 1.815 Mg m−3
Orthorhombic, Pnma	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2n	Cell parameters from 3130 reflections
a = 11.488 (2) Å	θ = 2.3–28.2°
b = 6.6085 (12) Å	µ = 2.50 mm−1
c = 14.650 (3) Å	T = 298 K
V = 1112.2 (4) Å3	Block, black
Z = 4	0.38 × 0.27 × 0.24 mm

Bruker SMART CCD area-detector diffractometer	1077 independent reflections
Radiation source: fine-focus sealed tube	947 reflections with I > 2σ(I)
graphite	Rint = 0.021
φ and ω scans	θmax = 25.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→13
Tmin = 0.44, Tmax = 0.55	k = −7→7
5593 measured reflections	l = −17→10

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.029	H-atom parameters constrained
wR(F2) = 0.080	w = 1/[σ2(Fo2) + (0.0469P)2 + 0.712P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
1077 reflections	Δρmax = 0.67 e Å−3
86 parameters	Δρmin = −0.54 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0072 (9)

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cu1	0.28439 (4)	0.2500	0.53244 (3)	0.0689 (3)
N1	0.1200 (2)	0.2500	0.25507 (19)	0.0338 (6)
H1A	0.1489	0.2500	0.2009	0.041*
H1B	0.0458	0.2500	0.2625	0.041*
N2	0.3047 (2)	0.2500	0.31376 (19)	0.0361 (7)
H2	0.3483	0.2500	0.3615	0.043*
N3	0.3600 (2)	0.2500	0.22780 (18)	0.0348 (6)
H3A	0.3244	0.1616	0.1914	0.052*	0.50
H3B	0.3555	0.3732	0.2035	0.052*	0.50
N4	0.4655 (2)	0.2500	0.7081 (2)	0.0457 (8)
H4A	0.5262	0.2500	0.7423	0.055*
H4B	0.4729	0.2500	0.6496	0.055*
N5	0.3516 (2)	0.2500	0.83438 (18)	0.0349 (7)
H5	0.2839	0.2500	0.8594	0.042*
N6	0.4526 (2)	0.2500	0.88959 (19)	0.0414 (7)
H6A	0.4426	0.1645	0.9359	0.062*	0.50
H6B	0.4647	0.3741	0.9112	0.062*	0.50
N7	0.4475 (3)	0.2500	0.4928 (2)	0.0415 (7)
S1	0.13368 (7)	0.2500	0.43541 (6)	0.0335 (2)
S2	0.23512 (7)	0.2500	0.68064 (5)	0.0318 (2)
S3	0.68866 (8)	0.2500	0.47665 (7)	0.0528 (3)
C1	0.1893 (3)	0.2500	0.3264 (2)	0.0283 (7)
C2	0.3611 (3)	0.2500	0.7450 (2)	0.0286 (7)
C3	0.5450 (3)	0.2500	0.4851 (2)	0.0278 (7)

	U11	U22	U33	U12	U13	U23
Cu1	0.0292 (3)	0.1520 (7)	0.0256 (3)	0.000	−0.00124 (17)	0.000
N1	0.0205 (13)	0.0557 (17)	0.0252 (13)	0.000	−0.0003 (10)	0.000
N2	0.0214 (13)	0.0632 (18)	0.0237 (14)	0.000	−0.0002 (11)	0.000
N3	0.0254 (13)	0.0517 (17)	0.0274 (15)	0.000	0.0048 (11)	0.000
N4	0.0261 (15)	0.088 (2)	0.0236 (14)	0.000	−0.0024 (11)	0.000
N5	0.0260 (13)	0.0529 (17)	0.0259 (15)	0.000	−0.0030 (11)	0.000
N6	0.0339 (15)	0.0617 (19)	0.0285 (15)	0.000	−0.0088 (12)	0.000
N7	0.0338 (18)	0.0549 (19)	0.0357 (16)	0.000	0.0011 (13)	0.000
S1	0.0242 (4)	0.0521 (5)	0.0242 (4)	0.000	0.0021 (3)	0.000
S2	0.0232 (4)	0.0477 (5)	0.0243 (4)	0.000	−0.0017 (3)	0.000
S3	0.0279 (5)	0.0971 (8)	0.0333 (5)	0.000	−0.0009 (4)	0.000
C1	0.0242 (15)	0.0345 (16)	0.0263 (16)	0.000	−0.0003 (12)	0.000
C2	0.0256 (15)	0.0335 (16)	0.0265 (16)	0.000	−0.0038 (12)	0.000
C3	0.0286 (18)	0.0395 (18)	0.0152 (14)	0.000	0.0017 (12)	0.000

Cu1—N7	1.962 (3)	N4—H4A	0.8600
Cu1—S1	2.2401 (10)	N4—H4B	0.8600
Cu1—S2	2.2437 (10)	N5—C2	1.314 (4)
N1—C1	1.313 (4)	N5—N6	1.414 (4)
N1—H1A	0.8600	N5—H5	0.8600
N1—H1B	0.8600	N6—H6A	0.8900
N2—C1	1.339 (4)	N6—H6B	0.8900
N2—N3	1.410 (4)	N7—C3	1.126 (4)
N2—H2	0.8600	S1—C1	1.721 (3)
N3—H3A	0.8900	S2—C2	1.727 (3)
N3—H3B	0.8900	S3—C3	1.655 (3)
N4—C2	1.315 (4)
N7—Cu1—S1	123.38 (10)	C2—N5—H5	119.9
N7—Cu1—S2	121.85 (10)	N6—N5—H5	119.9
S1—Cu1—S2	114.77 (4)	N5—N6—H6A	109.3
C1—N1—H1A	120.0	N5—N6—H6B	109.4
C1—N1—H1B	120.0	H6A—N6—H6B	109.5
H1A—N1—H1B	120.0	C3—N7—Cu1	168.5 (3)
C1—N2—N3	124.7 (3)	C1—S1—Cu1	107.58 (11)
C1—N2—H2	117.7	C2—S2—Cu1	108.46 (11)
N3—N2—H2	117.7	N1—C1—N2	119.4 (3)
N2—N3—H3A	109.2	N1—C1—S1	120.9 (2)
N2—N3—H3B	109.4	N2—C1—S1	119.7 (2)
H3A—N3—H3B	109.5	N5—C2—N4	119.0 (3)
C2—N4—H4A	120.0	N5—C2—S2	118.3 (2)
C2—N4—H4B	120.0	N4—C2—S2	122.7 (3)
H4A—N4—H4B	120.0	N7—C3—S3	178.6 (3)
C2—N5—N6	120.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···S3i	0.86	2.64	3.485 (3)	167.
N1—H1B···N3i	0.86	2.14	2.998 (4)	177.
N2—H2···N7	0.86	2.24	3.093 (4)	175.
N3—H3A···S2ii	0.89	2.81	3.5481 (11)	141.
N3—H3B···S2iii	0.89	2.72	3.5481 (11)	155.
N4—H4A···S2iv	0.86	2.65	3.501 (3)	170.
N4—H4B···N7	0.86	2.32	3.161 (4)	167.
N5—H5···S3v	0.86	2.64	3.342 (3)	140.
N6—H6A···S1vi	0.89	2.88	3.5144 (12)	130.
N6—H6B···S1vii	0.89	2.75	3.5144 (11)	144.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯S3i	0.86	2.64	3.485 (3)	167
N1—H1B⋯N3i	0.86	2.14	2.998 (4)	177
N2—H2⋯N7	0.86	2.24	3.093 (4)	175
N3—H3A⋯S2ii	0.89	2.81	3.5481 (11)	141
N3—H3B⋯S2iii	0.89	2.72	3.5481 (11)	155
N4—H4A⋯S2iv	0.86	2.65	3.501 (3)	170
N4—H4B⋯N7	0.86	2.32	3.161 (4)	167
N5—H5⋯S3v	0.86	2.64	3.342 (3)	140
N6—H6A⋯S1vi	0.89	2.88	3.5144 (12)	130
N6—H6B⋯S1vii	0.89	2.75	3.5144 (11)	144

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) .