Di-μ-bromido-bis-({2-[(4,6-dimethyl-pyrimidin-2-yl)disulfan-yl]-4,6-dimethyl-pyrimidine-κ(2)N(1),S(2)}copper(I)).

The title dinuclear complex, [Cu(2)Br(2)(C(12)H(14)N(4)S(2))(2)], is located about an inversion center. The Cu(I) ion is coordinated in a distorted tetra-hedral geometry by two bridging Br atoms in addition to an N and an S atom from the 2-[(4,6-dimethyl-pyrimidin-2-yl)disulfan-yl]-4,6-dimethyl-pyrimidine ligand. In the crystal, π-π stacking inter-actions are observed with a centroid-centroid distance of 3.590 (2) Å.

Related literature

For potential applications of heterocyclic thio­amides and their metal complexes, see: Battistuzzi & Peyronel (1981 ▶); Holm & Solomon (1996 ▶); Cox et al. (2006 ▶); Falcomer et al. (2006 ▶); Sevier & Kaiser (2006 ▶); Saxena et al. (2009 ▶). For related structures, see: Lemos et al. (2001 ▶); Aslanidis et al. (2004 ▶); Freeman et al. (2008 ▶).

Experimental

Crystal data

[Cu2Br2(C12H14N4S2)2]

M = 843.68

Monoclinic,

a = 15.3351 (7) Å

b = 15.3898 (7) Å

c = 14.3398 (7) Å

β = 109.178 (1)°

V = 3196.4 (3) Å3

Z = 4

Mo Kα radiation

μ = 4.12 mm−1

T = 293 K

0.21 × 0.18 × 0.10 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: integration (SADABS; Bruker, 2003 ▶) T min = 0.425, T max = 0.662

12339 measured reflections

2732 independent reflections

2344 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.077

S = 1.04

2732 reflections

181 parameters

55 restraints

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.31 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 2003 ▶); 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: SHELXL97 and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812016315/lh5449sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812016315/lh5449Isup2.hkl

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

[Cu2Br2(C12H14N4S2)2]	F(000) = 1680
Mr = 843.68	Dx = 1.753 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 16645 reflections
a = 15.3351 (7) Å	θ = 1.9–24.7°
b = 15.3898 (7) Å	µ = 4.12 mm−1
c = 14.3398 (7) Å	T = 293 K
β = 109.178 (1)°	Plate, colorless
V = 3196.4 (3) Å3	0.21 × 0.18 × 0.10 mm
Z = 4

Bruker SMART CCD diffractometer	2732 independent reflections
Radiation source: fine-focus sealed tube	2344 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
φ and ω scans	θmax = 24.7°, θmin = 1.9°
Absorption correction: integration (SADABS; Bruker, 2003)	h = −18→18
Tmin = 0.425, Tmax = 0.662	k = −18→17
12339 measured reflections	l = −16→16

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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.077	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0412P)2 + 3.1838P] where P = (Fo2 + 2Fc2)/3
2732 reflections	(Δ/σ)max = 0.001
181 parameters	Δρmax = 0.37 e Å−3
55 restraints	Δρmin = −0.31 e Å−3

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
C1A	0.12116 (19)	0.06625 (19)	0.6388 (2)	0.0437 (7)
C2A	0.0939 (2)	−0.0746 (2)	0.5935 (3)	0.0541 (8)
C3A	0.1153 (2)	−0.0561 (2)	0.5100 (3)	0.0559 (8)
H1A	0.1118	−0.0994	0.4637	0.067*
C4A	0.1417 (2)	0.0265 (2)	0.4949 (2)	0.0491 (7)
C5A	0.0690 (3)	−0.1640 (2)	0.6172 (4)	0.0806 (12)
H2A	0.0531	−0.1622	0.6766	0.097*
H4A	0.1206	−0.2022	0.6264	0.097*
H3A	0.0172	−0.1849	0.5637	0.097*
C6A	0.1667 (3)	0.0518 (3)	0.4062 (3)	0.0738 (11)
H7A	0.1835	0.1121	0.4107	0.089*
H5A	0.1147	0.0423	0.3477	0.089*
H6A	0.2178	0.0173	0.4033	0.089*
C1B	0.0927 (2)	0.3281 (2)	0.6662 (2)	0.0444 (7)
C2B	0.0657 (2)	0.4721 (2)	0.6545 (2)	0.0535 (8)
C3B	−0.0270 (2)	0.4533 (2)	0.6114 (2)	0.0572 (8)
H1B	−0.0700	0.4979	0.5910	0.069*
C4B	−0.0549 (2)	0.3680 (2)	0.5989 (2)	0.0534 (8)
C5B	0.1020 (3)	0.5630 (2)	0.6741 (3)	0.0741 (11)
H2B	0.1679	0.5614	0.7044	0.089*
H4B	0.0749	0.5914	0.7174	0.089*
H3B	0.0866	0.5943	0.6129	0.089*
C6B	−0.1546 (2)	0.3429 (3)	0.5541 (3)	0.0743 (11)
H5B	−0.1599	0.2807	0.5516	0.089*
H6B	−0.1787	0.3661	0.4885	0.089*
H7B	−0.1890	0.3658	0.5937	0.089*
Cu1	0.20241 (3)	0.20852 (2)	0.55473 (3)	0.05128 (14)
N1A	0.09541 (17)	−0.01146 (17)	0.65843 (19)	0.0522 (6)
N2A	0.14596 (16)	0.09016 (15)	0.56177 (17)	0.0420 (5)
N1B	0.12747 (18)	0.40741 (17)	0.68337 (19)	0.0515 (6)
N2B	0.00657 (18)	0.30262 (16)	0.62617 (19)	0.0491 (6)
S1A	0.12183 (7)	0.14055 (6)	0.73360 (6)	0.0591 (2)
S1B	0.18435 (6)	0.24973 (5)	0.70698 (6)	0.0506 (2)
Br1	0.13259 (2)	0.31106 (2)	0.42440 (3)	0.05795 (13)

	U11	U22	U33	U12	U13	U23
C1A	0.0383 (15)	0.0440 (16)	0.0466 (16)	0.0048 (12)	0.0110 (13)	0.0077 (13)
C2A	0.0375 (17)	0.0438 (17)	0.072 (2)	−0.0002 (13)	0.0056 (15)	0.0108 (16)
C3A	0.0514 (19)	0.0434 (17)	0.066 (2)	−0.0011 (14)	0.0099 (16)	−0.0083 (15)
C4A	0.0506 (18)	0.0460 (17)	0.0482 (17)	0.0027 (14)	0.0127 (14)	−0.0042 (14)
C5A	0.070 (3)	0.049 (2)	0.113 (3)	−0.0075 (18)	0.017 (2)	0.017 (2)
C6A	0.107 (3)	0.062 (2)	0.063 (2)	−0.011 (2)	0.042 (2)	−0.0166 (18)
C1B	0.0487 (17)	0.0486 (17)	0.0411 (16)	0.0076 (13)	0.0216 (13)	−0.0017 (13)
C2B	0.070 (2)	0.0468 (18)	0.0517 (18)	0.0055 (15)	0.0303 (16)	−0.0021 (14)
C3B	0.060 (2)	0.0566 (19)	0.059 (2)	0.0166 (15)	0.0256 (16)	0.0068 (16)
C4B	0.0501 (18)	0.063 (2)	0.0504 (18)	0.0081 (15)	0.0211 (14)	0.0066 (15)
C5B	0.092 (3)	0.051 (2)	0.083 (3)	0.0023 (19)	0.034 (2)	−0.0080 (19)
C6B	0.051 (2)	0.090 (3)	0.082 (3)	0.0056 (19)	0.0231 (18)	0.018 (2)
Cu1	0.0570 (3)	0.0424 (2)	0.0616 (3)	0.00037 (16)	0.0292 (2)	0.00422 (17)
N1A	0.0473 (14)	0.0483 (15)	0.0595 (16)	−0.0005 (12)	0.0157 (12)	0.0126 (13)
N2A	0.0429 (13)	0.0409 (13)	0.0426 (13)	−0.0011 (10)	0.0146 (10)	0.0018 (10)
N1B	0.0565 (16)	0.0476 (15)	0.0552 (15)	0.0014 (12)	0.0249 (12)	−0.0074 (12)
N2B	0.0477 (15)	0.0521 (15)	0.0501 (15)	0.0017 (12)	0.0197 (12)	0.0034 (12)
S1A	0.0828 (6)	0.0531 (5)	0.0510 (5)	0.0106 (4)	0.0351 (4)	0.0078 (4)
S1B	0.0495 (4)	0.0485 (5)	0.0521 (4)	0.0070 (3)	0.0142 (3)	−0.0062 (4)
Br1	0.0467 (2)	0.0548 (2)	0.0746 (3)	0.01020 (14)	0.02299 (17)	0.02122 (16)

C1A—N1A	1.319 (4)	C2B—C3B	1.381 (5)
C1A—N2A	1.332 (4)	C2B—C5B	1.498 (5)
C1A—S1A	1.774 (3)	C3B—C4B	1.375 (5)
C2A—N1A	1.341 (4)	C3B—H1B	0.9300
C2A—C3A	1.371 (5)	C4B—N2B	1.346 (4)
C2A—C5A	1.496 (4)	C4B—C6B	1.501 (5)
C3A—C4A	1.372 (4)	C5B—H2B	0.9600
C3A—H1A	0.9300	C5B—H4B	0.9600
C4A—N2A	1.358 (4)	C5B—H3B	0.9600
C4A—C6A	1.495 (5)	C6B—H5B	0.9600
C5A—H2A	0.9600	C6B—H6B	0.9600
C5A—H4A	0.9600	C6B—H7B	0.9600
C5A—H3A	0.9600	Cu1—N2A	2.033 (2)
C6A—H7A	0.9600	Cu1—S1B	2.3754 (9)
C6A—H5A	0.9600	Cu1—Br1	2.4114 (5)
C6A—H6A	0.9600	Cu1—Br1i	2.4669 (5)
C1B—N2B	1.315 (4)	Cu1—Cu1i	2.7801 (7)
C1B—N1B	1.323 (4)	S1A—S1B	2.0318 (13)
C1B—S1B	1.798 (3)	Br1—Cu1i	2.4668 (5)
C2B—N1B	1.342 (4)
N1A—C1A—N2A	127.9 (3)	C3B—C4B—C6B	122.1 (3)
N1A—C1A—S1A	110.3 (2)	C2B—C5B—H2B	109.5
N2A—C1A—S1A	121.7 (2)	C2B—C5B—H4B	109.5
N1A—C2A—C3A	120.0 (3)	H2B—C5B—H4B	109.5
N1A—C2A—C5A	117.2 (3)	C2B—C5B—H3B	109.5
C3A—C2A—C5A	122.8 (3)	H2B—C5B—H3B	109.5
C2A—C3A—C4A	119.9 (3)	H4B—C5B—H3B	109.5
C2A—C3A—H1A	120.0	C4B—C6B—H5B	109.5
C4A—C3A—H1A	120.0	C4B—C6B—H6B	109.5
N2A—C4A—C3A	120.3 (3)	H5B—C6B—H6B	109.5
N2A—C4A—C6A	116.5 (3)	C4B—C6B—H7B	109.5
C3A—C4A—C6A	123.2 (3)	H5B—C6B—H7B	109.5
C2A—C5A—H2A	109.5	H6B—C6B—H7B	109.5
C2A—C5A—H4A	109.5	N2A—Cu1—S1B	90.77 (7)
H2A—C5A—H4A	109.5	N2A—Cu1—Br1	122.47 (7)
C2A—C5A—H3A	109.5	S1B—Cu1—Br1	112.43 (3)
H2A—C5A—H3A	109.5	N2A—Cu1—Br1i	108.72 (7)
H4A—C5A—H3A	109.5	S1B—Cu1—Br1i	110.22 (3)
C4A—C6A—H7A	109.5	Br1—Cu1—Br1i	110.523 (16)
C4A—C6A—H5A	109.5	N2A—Cu1—Cu1i	138.63 (7)
H7A—C6A—H5A	109.5	S1B—Cu1—Cu1i	129.62 (3)
C4A—C6A—H6A	109.5	Br1—Cu1—Cu1i	56.200 (16)
H7A—C6A—H6A	109.5	Br1i—Cu1—Cu1i	54.323 (15)
H5A—C6A—H6A	109.5	C1A—N1A—C2A	116.6 (3)
N2B—C1B—N1B	129.9 (3)	C1A—N2A—C4A	115.2 (3)
N2B—C1B—S1B	120.5 (2)	C1A—N2A—Cu1	122.05 (19)
N1B—C1B—S1B	109.5 (2)	C4A—N2A—Cu1	122.3 (2)
N1B—C2B—C3B	120.1 (3)	C1B—N1B—C2B	115.2 (3)
N1B—C2B—C5B	116.9 (3)	C1B—N2B—C4B	114.3 (3)
C3B—C2B—C5B	123.0 (3)	C1A—S1A—S1B	105.86 (11)
C4B—C3B—C2B	119.3 (3)	C1B—S1B—S1A	104.42 (11)
C4B—C3B—H1B	120.4	C1B—S1B—Cu1	101.24 (10)
C2B—C3B—H1B	120.4	S1A—S1B—Cu1	99.01 (4)
N2B—C4B—C3B	121.2 (3)	Cu1—Br1—Cu1i	69.476 (16)
N2B—C4B—C6B	116.7 (3)