Dibromido(4,4'-dimethyl-2,2'-bipyridine-κ(2)N,N')(dimethyl sulfoxide-κO)cadmium.

In the title compound, [CdBr(2)(C(12)H(12)N(2))(C(2)H(6)OS)], the Cd(II) atom is five-coordinated in a distorted trigonal-bipyramidal geometry by two N atoms from one 4,4'-dimethyl-2,2'-bipyridine (DMBP) ligand, one O atom from a dimethyl sulfoxide (DMSO) ligand and two Br atoms. A weak intra-molecular C-H⋯O hydrogen bond occurs between the DMBP and DMSO ligands. π-π stacking between pyridine rings [centroid-centroid distances = 3.682 (3) and 3.598 (3) Å] is observed in the crystal.

Related literature

For related structures, see: Ahmadi et al. (2008 ▶); Alizadeh et al. (2010 ▶); Amani et al. (2009 ▶); Bellusci et al. (2008 ▶); Hojjat Kashani et al. (2008 ▶); Kalateh et al. (2008 ▶, 2010 ▶); Sakamoto et al. (2004 ▶); Shirvan & Haydari Dezfuli (2011 ▶); Sofetis et al. (2006 ▶); Willett et al. (2001 ▶); Yoshikawa et al. (2003 ▶); Yousefi et al. (2008 ▶).

Experimental

Crystal data

[CdBr2(C12H12N2)(C2H6OS)]

M = 534.58

Monoclinic,

a = 8.3940 (6) Å

b = 15.2928 (15) Å

c = 14.8606 (9) Å

β = 103.377 (5)°

V = 1855.9 (3) Å3

Z = 4

Mo Kα radiation

μ = 5.59 mm−1

T = 298 K

0.33 × 0.28 × 0.20 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.183, T max = 0.342

16741 measured reflections

4054 independent reflections

3008 reflections with I > 2σ(I)

R int = 0.099

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.086

S = 1.04

4054 reflections

190 parameters

H-atom parameters constrained

Δρmax = 0.53 e Å−3

Δρmin = −0.42 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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 datablock(s) I, global. DOI: 10.1107/S1600536812028553/xu5571sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812028553/xu5571Isup2.hkl

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

[CdBr2(C12H12N2)(C2H6OS)]	F(000) = 1032
Mr = 534.58	Dx = 1.913 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 10741 reflections
a = 8.3940 (6) Å	θ = 1.9–27.0°
b = 15.2928 (15) Å	µ = 5.59 mm−1
c = 14.8606 (9) Å	T = 298 K
β = 103.377 (5)°	Block, colorless
V = 1855.9 (3) Å3	0.33 × 0.28 × 0.20 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	4054 independent reflections
Radiation source: fine-focus sealed tube	3008 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.099
ω scans	θmax = 27.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −9→10
Tmin = 0.183, Tmax = 0.342	k = −19→19
16741 measured reflections	l = −18→18

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) = 0.086	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0279P)2 + 0.8746P] where P = (Fo2 + 2Fc2)/3
4054 reflections	(Δ/σ)max = 0.010
190 parameters	Δρmax = 0.53 e Å−3
0 restraints	Δρmin = −0.42 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
C1	0.0502 (6)	0.2148 (3)	0.6246 (3)	0.0501 (11)
H1	0.0521	0.2350	0.6838	0.060*
C2	−0.0370 (7)	0.2624 (3)	0.5505 (3)	0.0526 (12)
H2	−0.0933	0.3127	0.5599	0.063*
C3	−0.0391 (7)	0.2337 (3)	0.4611 (3)	0.0528 (12)
C4	−0.1294 (8)	0.2827 (4)	0.3769 (4)	0.0767 (18)
H4A	−0.0862	0.3409	0.3779	0.092*
H4B	−0.2437	0.2854	0.3769	0.092*
H4C	−0.1160	0.2529	0.3223	0.092*
C5	0.0474 (6)	0.1592 (3)	0.4529 (3)	0.0473 (11)
H5	0.0502	0.1387	0.3944	0.057*
C6	0.1305 (5)	0.1138 (2)	0.5302 (2)	0.0373 (9)
C7	0.2243 (5)	0.0322 (2)	0.5237 (3)	0.0365 (9)
C8	0.2297 (6)	−0.0049 (3)	0.4393 (3)	0.0426 (10)
H8	0.1732	0.0214	0.3848	0.051*
C9	0.3177 (6)	−0.0803 (3)	0.4350 (3)	0.0476 (11)
C10	0.3268 (7)	−0.1202 (3)	0.3438 (3)	0.0634 (14)
H10A	0.2846	−0.1787	0.3402	0.076*
H10B	0.4387	−0.1213	0.3387	0.076*
H10C	0.2629	−0.0858	0.2943	0.076*
C11	0.3983 (7)	−0.1162 (3)	0.5174 (3)	0.0535 (12)
H11	0.4593	−0.1670	0.5178	0.064*
C12	0.3894 (7)	−0.0776 (3)	0.5995 (3)	0.0539 (12)
H12	0.4446	−0.1034	0.6545	0.065*
C13	0.5760 (15)	−0.1667 (4)	0.8786 (5)	0.144 (4)
H13A	0.6672	−0.1729	0.8502	0.173*
H13B	0.4795	−0.1906	0.8385	0.173*
H13C	0.5987	−0.1973	0.9365	0.173*
C14	0.7460 (8)	−0.0254 (5)	0.9509 (4)	0.094 (2)
H14A	0.7545	0.0372	0.9532	0.112*
H14B	0.8195	−0.0483	0.9159	0.112*
H14C	0.7744	−0.0485	1.0126	0.112*
N1	0.1310 (5)	0.1425 (2)	0.6162 (2)	0.0418 (8)
N2	0.3045 (5)	−0.0041 (2)	0.6035 (2)	0.0424 (8)
Br1	0.35504 (9)	0.19185 (4)	0.84879 (4)	0.0779 (2)
Br2	0.07055 (8)	−0.04712 (4)	0.79461 (3)	0.06865 (18)
O1	0.5107 (5)	−0.0161 (3)	0.8016 (2)	0.0663 (10)
S1	0.54455 (17)	−0.05549 (9)	0.89770 (7)	0.0547 (3)
Cd1	0.27102 (4)	0.05814 (2)	0.741841 (19)	0.04315 (10)

	U11	U22	U33	U12	U13	U23
C1	0.065 (3)	0.048 (2)	0.040 (2)	0.002 (2)	0.017 (2)	−0.0086 (18)
C2	0.060 (3)	0.046 (2)	0.053 (3)	0.011 (2)	0.016 (2)	−0.002 (2)
C3	0.062 (3)	0.051 (3)	0.043 (2)	0.005 (2)	0.007 (2)	0.0069 (19)
C4	0.094 (5)	0.076 (4)	0.058 (3)	0.032 (3)	0.014 (3)	0.017 (3)
C5	0.060 (3)	0.051 (2)	0.030 (2)	0.000 (2)	0.0084 (19)	0.0015 (17)
C6	0.043 (2)	0.040 (2)	0.0296 (19)	−0.0028 (18)	0.0094 (17)	−0.0016 (15)
C7	0.042 (2)	0.0367 (19)	0.0315 (18)	−0.0094 (17)	0.0090 (17)	−0.0005 (14)
C8	0.049 (3)	0.048 (2)	0.0295 (19)	−0.003 (2)	0.0061 (18)	0.0004 (16)
C9	0.057 (3)	0.047 (2)	0.039 (2)	−0.004 (2)	0.012 (2)	−0.0054 (17)
C10	0.083 (4)	0.067 (3)	0.045 (3)	0.001 (3)	0.024 (3)	−0.011 (2)
C11	0.062 (3)	0.050 (3)	0.051 (3)	0.012 (2)	0.017 (2)	−0.003 (2)
C12	0.069 (3)	0.050 (3)	0.039 (2)	0.009 (2)	0.006 (2)	0.0047 (18)
C13	0.262 (13)	0.059 (4)	0.091 (5)	0.014 (6)	0.003 (7)	0.010 (3)
C14	0.075 (5)	0.144 (6)	0.055 (3)	−0.019 (4)	0.001 (3)	0.000 (4)
N1	0.050 (2)	0.0409 (18)	0.0332 (17)	−0.0013 (17)	0.0076 (16)	−0.0039 (14)
N2	0.050 (2)	0.0457 (19)	0.0309 (16)	0.0009 (17)	0.0077 (15)	0.0003 (14)
Br1	0.1001 (5)	0.0708 (3)	0.0542 (3)	−0.0152 (3)	0.0004 (3)	−0.0206 (2)
Br2	0.0777 (4)	0.0856 (4)	0.0417 (3)	−0.0271 (3)	0.0118 (2)	0.0113 (2)
O1	0.066 (2)	0.091 (2)	0.0404 (17)	0.022 (2)	0.0083 (16)	0.0151 (17)
S1	0.0557 (7)	0.0726 (7)	0.0358 (5)	0.0043 (7)	0.0102 (5)	0.0008 (5)
Cd1	0.0511 (2)	0.04968 (17)	0.02831 (14)	−0.00105 (16)	0.00838 (12)	0.00028 (12)

C1—N1	1.318 (6)	C10—H10B	0.9600
C1—C2	1.380 (7)	C10—H10C	0.9600
C1—H1	0.9300	C11—C12	1.372 (6)
C2—C3	1.394 (6)	C11—H11	0.9300
C2—H2	0.9300	C12—N2	1.339 (6)
C3—C5	1.373 (7)	C12—H12	0.9300
C3—C4	1.504 (7)	C13—S1	1.754 (7)
C4—H4A	0.9600	C13—H13A	0.9600
C4—H4B	0.9600	C13—H13B	0.9600
C4—H4C	0.9600	C13—H13C	0.9600
C5—C6	1.384 (6)	C14—S1	1.755 (6)
C5—H5	0.9300	C14—H14A	0.9600
C6—N1	1.351 (5)	C14—H14B	0.9600
C6—C7	1.489 (6)	C14—H14C	0.9600
C7—N2	1.342 (5)	Cd1—O1	2.301 (4)
C7—C8	1.387 (5)	Cd1—N1	2.349 (3)
C8—C9	1.378 (6)	Cd1—N2	2.340 (3)
C8—H8	0.9300	Cd1—Br1	2.5857 (6)
C9—C11	1.370 (6)	Cd1—Br2	2.5784 (6)
C9—C10	1.505 (6)	O1—S1	1.515 (3)
C10—H10A	0.9600
N1—C1—C2	123.8 (4)	C9—C11—H11	119.8
N1—C1—H1	118.1	C12—C11—H11	119.8
C2—C1—H1	118.1	N2—C12—C11	122.7 (4)
C1—C2—C3	118.8 (4)	N2—C12—H12	118.7
C1—C2—H2	120.6	C11—C12—H12	118.7
C3—C2—H2	120.6	S1—C13—H13A	109.5
C5—C3—C2	117.1 (4)	S1—C13—H13B	109.5
C5—C3—C4	121.0 (4)	H13A—C13—H13B	109.5
C2—C3—C4	121.9 (5)	S1—C13—H13C	109.5
C3—C4—H4A	109.5	H13A—C13—H13C	109.5
C3—C4—H4B	109.5	H13B—C13—H13C	109.5
H4A—C4—H4B	109.5	S1—C14—H14A	109.5
C3—C4—H4C	109.5	S1—C14—H14B	109.5
H4A—C4—H4C	109.5	H14A—C14—H14B	109.5
H4B—C4—H4C	109.5	S1—C14—H14C	109.5
C3—C5—C6	121.2 (4)	H14A—C14—H14C	109.5
C3—C5—H5	119.4	H14B—C14—H14C	109.5
C6—C5—H5	119.4	C1—N1—C6	118.3 (4)
N1—C6—C5	120.8 (4)	C1—N1—Cd1	124.0 (3)
N1—C6—C7	116.6 (3)	C6—N1—Cd1	117.7 (3)
C5—C6—C7	122.6 (3)	C12—N2—C7	118.1 (3)
N2—C7—C8	121.0 (4)	C12—N2—Cd1	123.6 (3)
N2—C7—C6	117.0 (3)	C7—N2—Cd1	118.1 (3)
C8—C7—C6	122.0 (4)	S1—O1—Cd1	121.1 (2)
C9—C8—C7	120.9 (4)	O1—S1—C13	103.6 (3)
C9—C8—H8	119.5	O1—S1—C14	105.7 (3)
C7—C8—H8	119.5	C13—S1—C14	99.3 (5)
C11—C9—C8	116.9 (4)	O1—Cd1—N2	82.34 (12)
C11—C9—C10	121.7 (4)	O1—Cd1—N1	144.06 (13)
C8—C9—C10	121.3 (4)	N2—Cd1—N1	70.41 (12)
C9—C10—H10A	109.5	O1—Cd1—Br2	98.54 (10)
C9—C10—H10B	109.5	N2—Cd1—Br2	103.45 (9)
H10A—C10—H10B	109.5	N1—Cd1—Br2	110.05 (9)
C9—C10—H10C	109.5	O1—Cd1—Br1	93.61 (10)
H10A—C10—H10C	109.5	N2—Cd1—Br1	142.22 (9)
H10B—C10—H10C	109.5	N1—Cd1—Br1	93.99 (8)
C9—C11—C12	120.3 (4)	Br2—Cd1—Br1	114.28 (2)
N1—C1—C2—C3	−0.9 (8)	C8—C7—N2—C12	−0.3 (6)
C1—C2—C3—C5	−0.2 (7)	C6—C7—N2—C12	179.9 (4)
C1—C2—C3—C4	−179.2 (5)	C8—C7—N2—Cd1	−175.5 (3)
C2—C3—C5—C6	1.1 (7)	C6—C7—N2—Cd1	4.6 (5)
C4—C3—C5—C6	−179.9 (5)	Cd1—O1—S1—C13	122.3 (5)
C3—C5—C6—N1	−1.0 (7)	Cd1—O1—S1—C14	−133.7 (3)
C3—C5—C6—C7	179.4 (4)	S1—O1—Cd1—N2	−145.6 (3)
N1—C6—C7—N2	−1.8 (6)	S1—O1—Cd1—N1	174.01 (19)
C5—C6—C7—N2	177.7 (4)	S1—O1—Cd1—Br2	−43.1 (3)
N1—C6—C7—C8	178.4 (4)	S1—O1—Cd1—Br1	72.1 (3)
C5—C6—C7—C8	−2.1 (6)	C12—N2—Cd1—O1	24.8 (4)
N2—C7—C8—C9	0.0 (7)	C7—N2—Cd1—O1	−160.3 (3)
C6—C7—C8—C9	179.8 (4)	C12—N2—Cd1—N1	−179.0 (4)
C7—C8—C9—C11	0.1 (7)	C7—N2—Cd1—N1	−4.1 (3)
C7—C8—C9—C10	−178.9 (5)	C12—N2—Cd1—Br2	−72.2 (4)
C8—C9—C11—C12	0.1 (8)	C7—N2—Cd1—Br2	102.7 (3)
C10—C9—C11—C12	179.1 (5)	C12—N2—Cd1—Br1	110.8 (4)
C9—C11—C12—N2	−0.4 (8)	C7—N2—Cd1—Br1	−74.3 (4)
C2—C1—N1—C6	1.0 (7)	C1—N1—Cd1—O1	−135.5 (4)
C2—C1—N1—Cd1	−177.5 (4)	C6—N1—Cd1—O1	46.0 (4)
C5—C6—N1—C1	0.0 (6)	C1—N1—Cd1—N2	−178.5 (4)
C7—C6—N1—C1	179.5 (4)	C6—N1—Cd1—N2	3.1 (3)
C5—C6—N1—Cd1	178.5 (3)	C1—N1—Cd1—Br2	83.9 (4)
C7—C6—N1—Cd1	−1.9 (5)	C6—N1—Cd1—Br2	−94.6 (3)
C11—C12—N2—C7	0.5 (7)	C1—N1—Cd1—Br1	−33.8 (4)
C11—C12—N2—Cd1	175.5 (4)	C6—N1—Cd1—Br1	147.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O1	0.93	2.51	3.087 (5)	120

Table 1

Selected bond lengths (Å)

Cd1—O1	2.301 (4)
Cd1—N1	2.349 (3)
Cd1—N2	2.340 (3)
Cd1—Br1	2.5857 (6)
Cd1—Br2	2.5784 (6)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯O1	0.93	2.51	3.087 (5)	120