(4,4'-Dimethyl-2,2'-bipyridine-κN,N')(dimethyl sulfoxide-κO)diiodidocadmium(II).

In the title compound, [CdI(2)(C(12)H(12)N(2))(C(2)H(6)OS)], the Cd(II) cation is coordinated by two N atoms from a dimethyl-bipyridine ligand, one O atom from a dimethyl sulfoxide mol-ecule and two I(-) anions in a distorted trigonal-bipyramidal geometry. Intra-molecular C-H⋯O hydrogen bonding and inter-molecular π-π stacking between parallel pyridine rings [centroid-centroid distance = 3.658 (3) Å] are present in the crystal structure.

Related literature

For metal complexes of 4,4′-dimethyl-2,2′-bipyridine, see: Ahmadi et al. (2008 ▶); Amani et al. (2009 ▶); Kalateh et al. (2008 ▶); Bellusci et al. (2008 ▶); Hojjat Kashani et al. (2008 ▶); Sakamoto et al. (2004 ▶); Sofetis et al. (2006 ▶); Willett et al. (2001 ▶); Yoshikawa et al. (2003 ▶); Yousefi et al. (2008 ▶).

Experimental

Crystal data

[CdI2(C12H12N2)(C2H6OS)]

M = 628.58

Monoclinic,

a = 8.729 (1) Å

b = 15.5247 (18) Å

c = 15.1354 (17) Å

β = 102.620 (9)°

V = 2001.5 (4) Å3

Z = 4

Mo Kα radiation

μ = 4.28 mm−1

T = 298 K

0.49 × 0.30 × 0.28 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1998 ▶) T min = 0.002, T max = 0.055

15568 measured reflections

5360 independent reflections

4625 reflections with I > 2σ(I)

R int = 0.082

Refinement

R[F 2 > 2σ(F 2)] = 0.066

wR(F 2) = 0.172

S = 1.16

5360 reflections

195 parameters

H-atom parameters constrained

Δρmax = 2.10 e Å−3

Δρmin = −2.23 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAIn class="Chemical">NT; 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: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810012572/xu2734sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810012572/xu2734Isup2.hkl

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

[CdI2(C12H12N2)(C2H6OS)]	F(000) = 1176
Mr = 628.58	Dx = 2.086 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 887 reflections
a = 8.729 (1) Å	θ = 1.9–29.3°
b = 15.5247 (18) Å	µ = 4.28 mm−1
c = 15.1354 (17) Å	T = 298 K
β = 102.620 (9)°	Block, colorless
V = 2001.5 (4) Å3	0.49 × 0.30 × 0.28 mm
Z = 4

Bruker SMART CCD diffractometer	5360 independent reflections
Radiation source: fine-focus sealed tube	4625 reflections with I > 2σ(I)
graphite	Rint = 0.082
φ and ω scans	θmax = 29.2°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1998)	h = −11→11
Tmin = 0.002, Tmax = 0.055	k = −21→20
15568 measured reflections	l = −20→19

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)] = 0.066	H-atom parameters constrained
wR(F2) = 0.172	w = 1/[σ2(Fo2) + (0.0903P)2 + 1.8883P] where P = (Fo2 + 2Fc2)/3
S = 1.16	(Δ/σ)max = 0.015
5360 reflections	Δρmax = 2.10 e Å−3
195 parameters	Δρmin = −2.23 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: 0.0171 (10)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.9509 (8)	0.7934 (4)	0.8795 (4)	0.0575 (14)
H1	0.9529	0.7743	0.8216	0.069*
C2	1.0322 (8)	0.7476 (4)	0.9527 (5)	0.0596 (14)
H2	1.0897	0.6991	0.9439	0.071*
C3	1.0280 (8)	0.7741 (4)	1.0397 (4)	0.0584 (14)
C4	1.1139 (11)	0.7258 (6)	1.1206 (6)	0.082 (2)
H4C	1.1322	0.7630	1.1725	0.098*
H4B	1.2126	0.7060	1.1101	0.098*
H4A	1.0522	0.6773	1.1313	0.098*
C5	0.9435 (7)	0.8469 (4)	1.0476 (4)	0.0499 (12)
H5	0.9383	0.8666	1.1049	0.060*
C6	0.8651 (5)	0.8918 (3)	0.9714 (3)	0.0385 (9)
C7	0.7726 (5)	0.9709 (3)	0.9790 (3)	0.0385 (9)
C8	0.7692 (6)	1.0072 (4)	1.0620 (3)	0.0453 (10)
H8	0.8262	0.9825	1.1151	0.054*
C9	0.6794 (7)	1.0810 (4)	1.0656 (4)	0.0488 (11)
C10	0.6735 (10)	1.1201 (5)	1.1561 (4)	0.0679 (17)
H10A	0.7188	1.1767	1.1603	0.081*
H10B	0.7315	1.0846	1.2037	0.081*
H10C	0.5663	1.1239	1.1617	0.081*
C11	0.5989 (8)	1.1146 (4)	0.9857 (4)	0.0568 (13)
H11	0.5372	1.1635	0.9857	0.068*
C12	0.6086 (8)	1.0764 (4)	0.9054 (4)	0.0545 (13)
H12	0.5546	1.1013	0.8517	0.065*
C13	0.411 (3)	1.1614 (9)	0.6212 (9)	0.189 (11)
H13A	0.3652	1.1675	0.6730	0.227*
H13B	0.3365	1.1789	0.5677	0.227*
H13C	0.5029	1.1971	0.6287	0.227*
C14	0.2811 (10)	1.0103 (11)	0.5584 (6)	0.110 (4)
H14C	0.2942	0.9510	0.5437	0.132*
H14B	0.2383	1.0418	0.5040	0.132*
H14A	0.2108	1.0141	0.5989	0.132*
N1	0.8687 (5)	0.8647 (3)	0.8888 (3)	0.0471 (9)
N2	0.6925 (5)	1.0048 (3)	0.9006 (3)	0.0439 (9)
O1	0.4994 (6)	1.0216 (4)	0.7072 (3)	0.0664 (12)
Cd1	0.72703 (5)	0.94561 (3)	0.76515 (2)	0.04529 (16)
I1	0.93442 (5)	1.04931 (3)	0.70096 (3)	0.06676 (19)
I2	0.63195 (7)	0.80423 (3)	0.65550 (3)	0.0758 (2)
S1	0.46338 (19)	1.05399 (12)	0.61041 (10)	0.0574 (4)

	U11	U22	U33	U12	U13	U23
C1	0.068 (3)	0.057 (3)	0.046 (3)	0.009 (3)	0.008 (2)	−0.013 (2)
C2	0.066 (3)	0.056 (3)	0.055 (3)	0.014 (3)	0.010 (3)	−0.008 (3)
C3	0.062 (3)	0.055 (3)	0.056 (3)	0.010 (3)	0.007 (3)	0.003 (3)
C4	0.094 (5)	0.082 (5)	0.063 (4)	0.032 (4)	0.006 (4)	0.008 (4)
C5	0.055 (3)	0.054 (3)	0.038 (2)	0.008 (2)	0.005 (2)	0.000 (2)
C6	0.038 (2)	0.042 (2)	0.036 (2)	−0.0003 (16)	0.0086 (16)	0.0007 (18)
C7	0.037 (2)	0.045 (2)	0.033 (2)	−0.0025 (17)	0.0059 (16)	−0.0002 (18)
C8	0.054 (3)	0.050 (3)	0.031 (2)	0.003 (2)	0.0069 (18)	−0.0019 (19)
C9	0.055 (3)	0.048 (3)	0.045 (3)	0.002 (2)	0.013 (2)	−0.003 (2)
C10	0.090 (5)	0.070 (4)	0.046 (3)	0.011 (4)	0.019 (3)	−0.009 (3)
C11	0.068 (3)	0.051 (3)	0.050 (3)	0.013 (3)	0.010 (3)	−0.004 (2)
C12	0.069 (3)	0.055 (3)	0.036 (2)	0.014 (3)	0.002 (2)	0.002 (2)
C13	0.38 (3)	0.084 (8)	0.079 (7)	0.051 (13)	−0.012 (12)	0.009 (6)
C14	0.061 (4)	0.200 (13)	0.063 (5)	−0.027 (6)	0.001 (4)	−0.007 (7)
N1	0.050 (2)	0.053 (2)	0.038 (2)	−0.0004 (18)	0.0086 (17)	−0.0057 (18)
N2	0.048 (2)	0.048 (2)	0.0333 (18)	0.0019 (17)	0.0039 (16)	−0.0008 (17)
O1	0.059 (2)	0.095 (4)	0.042 (2)	0.014 (2)	0.0060 (18)	0.010 (2)
Cd1	0.0492 (2)	0.0532 (3)	0.0323 (2)	−0.00441 (14)	0.00650 (14)	−0.00210 (14)
I1	0.0659 (3)	0.0866 (4)	0.0452 (2)	−0.0248 (2)	0.00653 (18)	0.01257 (19)
I2	0.0940 (4)	0.0675 (3)	0.0581 (3)	−0.0181 (2)	−0.0001 (2)	−0.0193 (2)
S1	0.0532 (7)	0.0810 (11)	0.0364 (6)	0.0013 (6)	0.0061 (5)	−0.0011 (6)

C1—N1	1.342 (8)	C10—H10B	0.9600
C1—C2	1.376 (9)	C10—H10C	0.9600
C1—H1	0.9300	C11—C12	1.373 (8)
C2—C3	1.387 (9)	C11—H11	0.9300
C2—H2	0.9300	C12—N2	1.342 (8)
C3—C5	1.368 (8)	C12—H12	0.9300
C3—C4	1.491 (9)	C13—S1	1.746 (13)
C4—H4C	0.9600	C13—H13A	0.9600
C4—H4B	0.9600	C13—H13B	0.9600
C4—H4A	0.9600	C13—H13C	0.9600
C5—C6	1.393 (7)	C14—S1	1.751 (9)
C5—H5	0.9300	C14—H14C	0.9600
C6—N1	1.327 (6)	C14—H14B	0.9600
C6—C7	1.487 (7)	C14—H14A	0.9600
C7—N2	1.346 (6)	Cd1—N1	2.366 (5)
C7—C8	1.384 (7)	Cd1—N2	2.326 (4)
C8—C9	1.396 (8)	O1—S1	1.515 (5)
C8—H8	0.9300	Cd1—O1	2.313 (5)
C9—C11	1.363 (9)	Cd1—I1	2.7535 (6)
C9—C10	1.508 (8)	Cd1—I2	2.7674 (6)
C10—H10A	0.9600
N1—C1—C2	122.4 (6)	C9—C11—H11	120.0
N1—C1—H1	118.8	C12—C11—H11	120.0
C2—C1—H1	118.8	N2—C12—C11	123.1 (5)
C1—C2—C3	119.6 (6)	N2—C12—H12	118.5
C1—C2—H2	120.2	C11—C12—H12	118.5
C3—C2—H2	120.2	S1—C13—H13A	109.5
C5—C3—C2	117.0 (6)	S1—C13—H13B	109.5
C5—C3—C4	121.8 (6)	H13A—C13—H13B	109.5
C2—C3—C4	121.1 (6)	S1—C13—H13C	109.5
C3—C4—H4C	109.5	H13A—C13—H13C	109.5
C3—C4—H4B	109.5	H13B—C13—H13C	109.5
H4C—C4—H4B	109.5	S1—C14—H14C	109.5
C3—C4—H4A	109.5	S1—C14—H14B	109.5
H4C—C4—H4A	109.5	H14C—C14—H14B	109.5
H4B—C4—H4A	109.5	S1—C14—H14A	109.5
C3—C5—C6	121.2 (5)	H14C—C14—H14A	109.5
C3—C5—H5	119.4	H14B—C14—H14A	109.5
C6—C5—H5	119.4	C6—N1—C1	118.9 (5)
N1—C6—C5	120.9 (5)	C6—N1—Cd1	117.5 (4)
N1—C6—C7	117.4 (4)	C1—N1—Cd1	123.6 (4)
C5—C6—C7	121.8 (4)	C12—N2—C7	117.5 (5)
N2—C7—C8	122.1 (5)	C12—N2—Cd1	123.5 (3)
N2—C7—C6	116.2 (4)	C7—N2—Cd1	118.7 (3)
C8—C7—C6	121.7 (4)	S1—O1—Cd1	121.0 (3)
C7—C8—C9	119.6 (5)	O1—Cd1—N2	82.36 (16)
C7—C8—H8	120.2	O1—Cd1—N1	145.92 (16)
C9—C8—H8	120.2	N2—Cd1—N1	70.02 (16)
C11—C9—C8	117.7 (5)	O1—Cd1—I1	98.31 (14)
C11—C9—C10	122.5 (6)	N2—Cd1—I1	107.57 (12)
C8—C9—C10	119.8 (5)	N1—Cd1—I1	108.61 (12)
C9—C10—H10A	109.5	O1—Cd1—I2	93.25 (14)
C9—C10—H10B	109.5	N2—Cd1—I2	139.68 (12)
H10A—C10—H10B	109.5	N1—Cd1—I2	95.15 (12)
C9—C10—H10C	109.5	I1—Cd1—I2	112.72 (2)
H10A—C10—H10C	109.5	O1—S1—C13	103.3 (5)
H10B—C10—H10C	109.5	O1—S1—C14	106.4 (5)
C9—C11—C12	120.0 (6)	C13—S1—C14	100.5 (9)
N1—C1—C2—C3	1.3 (11)	C8—C7—N2—C12	0.5 (8)
C1—C2—C3—C5	−1.2 (11)	C6—C7—N2—C12	−179.7 (5)
C1—C2—C3—C4	179.6 (8)	C8—C7—N2—Cd1	174.2 (4)
C2—C3—C5—C6	0.2 (10)	C6—C7—N2—Cd1	−6.0 (6)
C4—C3—C5—C6	179.4 (7)	S1—O1—Cd1—N2	152.1 (4)
C3—C5—C6—N1	0.8 (9)	S1—O1—Cd1—N1	−172.4 (3)
C3—C5—C6—C7	179.9 (6)	S1—O1—Cd1—I1	45.3 (4)
N1—C6—C7—N2	4.0 (7)	S1—O1—Cd1—I2	−68.2 (4)
C5—C6—C7—N2	−175.1 (5)	C12—N2—Cd1—O1	−22.7 (5)
N1—C6—C7—C8	−176.1 (5)	C7—N2—Cd1—O1	164.0 (4)
C5—C6—C7—C8	4.8 (8)	C12—N2—Cd1—N1	177.6 (5)
N2—C7—C8—C9	0.4 (8)	C7—N2—Cd1—N1	4.3 (4)
C6—C7—C8—C9	−179.4 (5)	C12—N2—Cd1—I1	73.7 (5)
C7—C8—C9—C11	−0.4 (9)	C7—N2—Cd1—I1	−99.6 (4)
C7—C8—C9—C10	179.2 (6)	C12—N2—Cd1—I2	−108.7 (5)
C8—C9—C11—C12	−0.5 (10)	C7—N2—Cd1—I2	78.0 (4)
C10—C9—C11—C12	180.0 (7)	C6—N1—Cd1—O1	−39.9 (6)
C9—C11—C12—N2	1.5 (11)	C1—N1—Cd1—O1	139.8 (5)
C5—C6—N1—C1	−0.8 (8)	C6—N1—Cd1—N2	−2.0 (4)
C7—C6—N1—C1	−179.9 (5)	C1—N1—Cd1—N2	177.7 (5)
C5—C6—N1—Cd1	179.0 (4)	C6—N1—Cd1—I1	100.5 (4)
C7—C6—N1—Cd1	−0.2 (6)	C1—N1—Cd1—I1	−79.8 (5)
C2—C1—N1—C6	−0.3 (10)	C6—N1—Cd1—I2	−143.5 (4)
C2—C1—N1—Cd1	−180.0 (5)	C1—N1—Cd1—I2	36.2 (5)
C11—C12—N2—C7	−1.4 (10)	Cd1—O1—S1—C13	−131.6 (9)
C11—C12—N2—Cd1	−174.8 (5)	Cd1—O1—S1—C14	123.1 (6)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O1	0.93	2.47	3.063 (8)	122

Table 1

Selected bond lengths (Å)

Cd1—N1	2.366 (5)
Cd1—N2	2.326 (4)
Cd1—O1	2.313 (5)
Cd1—I1	2.7535 (6)
Cd1—I2	2.7674 (6)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯O1	0.93	2.47	3.063 (8)	122