Dibromido(dimethyl sulfoxide-κO)(6-methyl-2,2'-bipyridine-κ(2)N,N')cadmium.

In the title compound, [CdBr(2)(C(11)H(10)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 a 6-methyl-2,2'-bipyridine ligand, one O atom from a dimethyl sulfoxide ligand and two Br atoms. An intra-molecular C-H⋯O hydrogen bond occurs. The crystal structure is stabilized by C-H⋯Br hydrogen bonds and π-π contacts between the pyridine rings [centroid-centroid distances = 3.582 (5) and 3.582 (5) Å].

Related literature

For related structures, see: Ahmadi et al. (2009 ▶); Ahmadi, Ebadi et al. (2008 ▶); Ahmadi, Kalateh et al. (2008 ▶); Alizadeh et al. (2009 ▶); Amani et al. (2009 ▶); Kalateh et al. (2010 ▶); Newkome et al. (1982 ▶); Onggo et al. (1990 ▶, 2005 ▶); Shirvan & Haydari Dezfuli (2012a ▶,b ▶).

Experimental

Crystal data

[CdBr2(C11H10N2)(C2H6OS)]

M = 520.56

Monoclinic,

a = 9.0169 (6) Å

b = 14.5503 (8) Å

c = 14.1473 (8) Å

β = 106.561 (5)°

V = 1779.11 (18) Å3

Z = 4

Mo Kα radiation

μ = 5.83 mm−1

T = 293 K

0.40 × 0.35 × 0.30 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.070, T max = 0.240

14429 measured reflections

3487 independent reflections

2683 reflections with I > 2σ(I)

R int = 0.114

Refinement

R[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.175

S = 1.05

3487 reflections

181 parameters

H-atom parameters constrained

Δρmax = 1.35 e Å−3

Δρmin = −1.58 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/S1600536812033168/hy2573sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812033168/hy2573Isup2.hkl

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

[CdBr2(C11H10N2)(C2H6OS)]	F(000) = 1000
Mr = 520.56	Dx = 1.944 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 14429 reflections
a = 9.0169 (6) Å	θ = 2.1–26.0°
b = 14.5503 (8) Å	µ = 5.83 mm−1
c = 14.1473 (8) Å	T = 293 K
β = 106.561 (5)°	Prism, colorless
V = 1779.11 (18) Å3	0.40 × 0.35 × 0.30 mm
Z = 4

Bruker APEXII CCD diffractometer	3487 independent reflections
Radiation source: fine-focus sealed tube	2683 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.114
φ and ω scans	θmax = 26.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −11→11
Tmin = 0.070, Tmax = 0.240	k = −17→17
14429 measured reflections	l = −17→17

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.175	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.1108P)2 + 0.213P] where P = (Fo2 + 2Fc2)/3
3487 reflections	(Δ/σ)max = 0.013
181 parameters	Δρmax = 1.35 e Å−3
0 restraints	Δρmin = −1.58 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	0.0526 (15)	0.2406 (9)	0.7072 (8)	0.095 (3)
H1A	0.1571	0.2589	0.7393	0.113*
H1B	0.0242	0.1907	0.7429	0.113*
H1C	−0.0157	0.2916	0.7054	0.113*
C2	0.0404 (10)	0.2109 (6)	0.6057 (7)	0.065 (2)
C3	−0.0649 (10)	0.2488 (7)	0.5244 (8)	0.076 (3)
H3	−0.1261	0.2979	0.5328	0.092*
C4	−0.0804 (11)	0.2160 (8)	0.4338 (9)	0.081 (3)
H4	−0.1515	0.2420	0.3794	0.098*
C5	0.0106 (10)	0.1432 (7)	0.4221 (7)	0.067 (2)
H5	0.0003	0.1189	0.3598	0.080*
C6	0.1172 (8)	0.1066 (5)	0.5039 (5)	0.0488 (16)
C7	0.2177 (8)	0.0275 (5)	0.4957 (5)	0.0489 (16)
C8	0.2191 (11)	−0.0105 (7)	0.4065 (6)	0.068 (2)
H8	0.1547	0.0137	0.3484	0.081*
C9	0.3133 (12)	−0.0828 (7)	0.4019 (8)	0.074 (3)
H9	0.3140	−0.1083	0.3417	0.089*
C10	0.4061 (11)	−0.1164 (6)	0.4886 (8)	0.071 (2)
H10	0.4726	−0.1652	0.4884	0.085*
C11	0.4012 (10)	−0.0778 (5)	0.5767 (7)	0.0589 (19)
H11	0.4628	−0.1025	0.6354	0.071*
C12	0.5881 (18)	−0.1426 (8)	0.9498 (9)	0.107 (4)
H12A	0.6375	−0.1857	0.9173	0.129*
H12B	0.4818	−0.1598	0.9392	0.129*
H12C	0.6399	−0.1426	1.0193	0.129*
C13	0.7939 (16)	−0.0279 (16)	0.9055 (11)	0.135 (6)
H13A	0.8121	0.0255	0.8706	0.162*
H13B	0.8204	−0.0821	0.8751	0.162*
H13C	0.8565	−0.0247	0.9728	0.162*
N1	0.1290 (7)	0.1384 (4)	0.5931 (5)	0.0517 (14)
N2	0.3111 (7)	−0.0063 (4)	0.5802 (4)	0.0466 (13)
Cd1	0.31578 (6)	0.06461 (3)	0.72653 (4)	0.0479 (2)
Br1	0.49691 (15)	0.19974 (7)	0.79147 (9)	0.0879 (4)
Br2	0.14174 (14)	−0.00070 (10)	0.82432 (8)	0.0931 (4)
O1	0.5147 (9)	−0.0376 (5)	0.7936 (5)	0.0803 (19)
S1	0.5972 (3)	−0.03236 (15)	0.90188 (15)	0.0594 (5)

	U11	U22	U33	U12	U13	U23
C1	0.116 (9)	0.091 (7)	0.083 (7)	0.038 (7)	0.039 (7)	−0.005 (6)
C2	0.058 (5)	0.066 (5)	0.073 (5)	0.013 (4)	0.023 (4)	0.007 (4)
C3	0.059 (5)	0.075 (6)	0.100 (8)	0.024 (4)	0.031 (5)	0.027 (6)
C4	0.058 (5)	0.097 (7)	0.083 (7)	0.013 (5)	0.012 (5)	0.025 (6)
C5	0.061 (5)	0.078 (6)	0.058 (5)	−0.001 (4)	0.012 (4)	0.009 (4)
C6	0.040 (3)	0.061 (4)	0.044 (4)	−0.008 (3)	0.011 (3)	0.007 (3)
C7	0.039 (4)	0.057 (4)	0.053 (4)	−0.008 (3)	0.018 (3)	−0.002 (3)
C8	0.059 (5)	0.096 (7)	0.048 (4)	−0.011 (5)	0.016 (4)	−0.014 (4)
C9	0.074 (6)	0.086 (6)	0.069 (6)	−0.009 (5)	0.030 (5)	−0.031 (5)
C10	0.069 (5)	0.057 (5)	0.096 (7)	−0.006 (4)	0.040 (5)	−0.026 (5)
C11	0.061 (5)	0.043 (4)	0.076 (5)	0.002 (3)	0.024 (4)	0.000 (3)
C12	0.160 (13)	0.088 (8)	0.076 (7)	−0.006 (8)	0.036 (8)	0.005 (6)
C13	0.080 (8)	0.24 (2)	0.086 (8)	0.027 (11)	0.026 (7)	0.010 (11)
N1	0.047 (3)	0.059 (4)	0.050 (3)	0.006 (3)	0.016 (3)	0.004 (3)
N2	0.048 (3)	0.050 (3)	0.045 (3)	−0.007 (2)	0.017 (3)	−0.005 (2)
Cd1	0.0532 (3)	0.0472 (3)	0.0421 (3)	−0.0042 (2)	0.0116 (2)	−0.0013 (2)
Br1	0.1072 (9)	0.0657 (6)	0.0866 (7)	−0.0300 (5)	0.0210 (6)	−0.0116 (5)
Br2	0.0902 (8)	0.1284 (10)	0.0644 (6)	−0.0346 (7)	0.0277 (5)	0.0009 (6)
O1	0.092 (5)	0.075 (4)	0.057 (3)	0.029 (4)	−0.006 (3)	−0.006 (3)
S1	0.0658 (12)	0.0625 (11)	0.0515 (10)	0.0095 (9)	0.0194 (9)	−0.0025 (9)

C1—C2	1.472 (14)	C9—H9	0.9300
C1—H1A	0.9600	C10—C11	1.378 (13)
C1—H1B	0.9600	C10—H10	0.9300
C1—H1C	0.9600	C11—N2	1.329 (10)
C2—N1	1.365 (10)	C11—H11	0.9300
C2—C3	1.381 (13)	C12—S1	1.752 (12)
C3—C4	1.337 (15)	C12—H12A	0.9600
C3—H3	0.9300	C12—H12B	0.9600
C4—C5	1.378 (14)	C12—H12C	0.9600
C4—H4	0.9300	C13—S1	1.761 (14)
C5—C6	1.383 (11)	C13—H13A	0.9600
C5—H5	0.9300	C13—H13B	0.9600
C6—N1	1.320 (10)	C13—H13C	0.9600
C6—C7	1.489 (11)	N1—Cd1	2.396 (6)
C7—N2	1.345 (10)	N2—Cd1	2.303 (6)
C7—C8	1.380 (11)	Cd1—O1	2.316 (6)
C8—C9	1.366 (14)	Cd1—Br2	2.5530 (12)
C8—H8	0.9300	Cd1—Br1	2.5539 (11)
C9—C10	1.364 (15)	O1—S1	1.502 (6)
C2—C1—H1A	109.5	N2—C11—H11	119.0
C2—C1—H1B	109.5	C10—C11—H11	119.0
H1A—C1—H1B	109.5	S1—C12—H12A	109.5
C2—C1—H1C	109.5	S1—C12—H12B	109.5
H1A—C1—H1C	109.5	H12A—C12—H12B	109.5
H1B—C1—H1C	109.5	S1—C12—H12C	109.5
N1—C2—C3	119.2 (9)	H12A—C12—H12C	109.5
N1—C2—C1	118.1 (8)	H12B—C12—H12C	109.5
C3—C2—C1	122.5 (9)	S1—C13—H13A	109.5
C4—C3—C2	121.0 (9)	S1—C13—H13B	109.5
C4—C3—H3	119.5	H13A—C13—H13B	109.5
C2—C3—H3	119.5	S1—C13—H13C	109.5
C3—C4—C5	119.1 (9)	H13A—C13—H13C	109.5
C3—C4—H4	120.5	H13B—C13—H13C	109.5
C5—C4—H4	120.5	C6—N1—C2	120.4 (7)
C4—C5—C6	119.5 (9)	C6—N1—Cd1	116.3 (5)
C4—C5—H5	120.3	C2—N1—Cd1	123.3 (6)
C6—C5—H5	120.3	C11—N2—C7	119.2 (7)
N1—C6—C5	120.7 (8)	C11—N2—Cd1	122.0 (6)
N1—C6—C7	117.4 (6)	C7—N2—Cd1	118.8 (5)
C5—C6—C7	121.8 (7)	N2—Cd1—O1	83.9 (2)
N2—C7—C8	119.9 (8)	N2—Cd1—N1	70.4 (2)
N2—C7—C6	117.0 (6)	O1—Cd1—N1	154.1 (2)
C8—C7—C6	123.0 (8)	N2—Cd1—Br2	117.63 (15)
C9—C8—C7	121.4 (9)	O1—Cd1—Br2	93.6 (2)
C9—C8—H8	119.3	N1—Cd1—Br2	101.02 (15)
C7—C8—H8	119.3	N2—Cd1—Br1	120.97 (14)
C10—C9—C8	117.6 (8)	O1—Cd1—Br1	90.3 (2)
C10—C9—H9	121.2	N1—Cd1—Br1	99.92 (16)
C8—C9—H9	121.2	Br2—Cd1—Br1	121.36 (4)
C9—C10—C11	119.9 (9)	S1—O1—Cd1	119.1 (4)
C9—C10—H10	120.1	O1—S1—C12	106.5 (5)
C11—C10—H10	120.1	O1—S1—C13	103.5 (6)
N2—C11—C10	122.0 (9)	C12—S1—C13	100.4 (9)
N1—C2—C3—C4	−0.5 (14)	C6—C7—N2—C11	179.0 (6)
C1—C2—C3—C4	−175.4 (11)	C8—C7—N2—Cd1	176.3 (6)
C2—C3—C4—C5	0.1 (16)	C6—C7—N2—Cd1	−3.1 (8)
C3—C4—C5—C6	−1.0 (15)	C11—N2—Cd1—O1	3.9 (6)
C4—C5—C6—N1	2.4 (13)	C7—N2—Cd1—O1	−174.0 (5)
C4—C5—C6—C7	179.6 (8)	C11—N2—Cd1—N1	−179.4 (6)
N1—C6—C7—N2	1.1 (10)	C7—N2—Cd1—N1	2.7 (5)
C5—C6—C7—N2	−176.2 (7)	C11—N2—Cd1—Br2	−87.0 (6)
N1—C6—C7—C8	−178.3 (7)	C7—N2—Cd1—Br2	95.1 (5)
C5—C6—C7—C8	4.4 (11)	C11—N2—Cd1—Br1	90.6 (6)
N2—C7—C8—C9	0.5 (12)	C7—N2—Cd1—Br1	−87.3 (5)
C6—C7—C8—C9	179.8 (8)	C6—N1—Cd1—N2	−2.1 (5)
C7—C8—C9—C10	0.0 (14)	C2—N1—Cd1—N2	179.5 (7)
C8—C9—C10—C11	0.7 (14)	C6—N1—Cd1—O1	5.5 (9)
C9—C10—C11—N2	−1.9 (13)	C2—N1—Cd1—O1	−173.0 (7)
C5—C6—N1—C2	−2.8 (11)	C6—N1—Cd1—Br2	−117.7 (5)
C7—C6—N1—C2	179.8 (7)	C2—N1—Cd1—Br2	63.9 (6)
C5—C6—N1—Cd1	178.6 (6)	C6—N1—Cd1—Br1	117.4 (5)
C7—C6—N1—Cd1	1.3 (8)	C2—N1—Cd1—Br1	−61.1 (6)
C3—C2—N1—C6	1.9 (12)	N2—Cd1—O1—S1	177.1 (5)
C1—C2—N1—C6	177.0 (9)	N1—Cd1—O1—S1	169.9 (4)
C3—C2—N1—Cd1	−179.7 (6)	Br2—Cd1—O1—S1	−65.5 (5)
C1—C2—N1—Cd1	−4.6 (12)	Br1—Cd1—O1—S1	55.9 (5)
C10—C11—N2—C7	2.4 (11)	Cd1—O1—S1—C12	126.0 (7)
C10—C11—N2—Cd1	−175.5 (6)	Cd1—O1—S1—C13	−128.7 (9)
C8—C7—N2—C11	−1.6 (10)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O1	0.93	2.35	3.003 (12)	127
C13—H13C···Br2i	0.96	2.89	3.722 (15)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯O1	0.93	2.35	3.003 (12)	127
C13—H13C⋯Br2i	0.96	2.89	3.722 (15)	146

Symmetry code: (i) .