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

In the title compound, [ZnI(2)(C(12)H(12)N(2))(C(2)H(6)OS)], the Zn(II) ion is coordinated by two N atoms from a 4,4'-dimethyl-2,2'-bipyridine ligand, one O atom from a dimethyl sulfoxide mol-ecule and two I atoms in a distorted trigonal-bipyramidal geometry. Intra-molecular C-H⋯O hydrogen bonds and inter-molecular π-π stacking inter-actions between the pyridine rings [centroid-centroid distances = 3.637 (4) and 3.818 (4) Å] are present in the crystal structure.

Related literature

For metal complexes of 4,4′-dimethyl-2,2′-bipyridine, 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 ▶); Sofetis et al. (2006 ▶); Willett et al. (2001 ▶); Yoshikawa et al. (2003 ▶); Yousefi et al. (2008 ▶).

Experimental

Crystal data

[ZnI2(C12H12N2)(C2H6OS)]

M = 581.56

Monoclinic,

a = 8.6173 (7) Å

b = 15.5424 (11) Å

c = 14.8976 (10) Å

β = 102.908 (6)°

V = 1944.9 (3) Å3

Z = 4

Mo Kα radiation

μ = 4.54 mm−1

T = 298 K

0.40 × 0.20 × 0.10 mm

Data collection

Bruker APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.350, T max = 0.636

21034 measured reflections

5243 independent reflections

4246 reflections with I > 2σ(I)

R int = 0.113

Refinement

R[F 2 > 2σ(F 2)] = 0.076

wR(F 2) = 0.202

S = 1.20

5243 reflections

191 parameters

H-atom parameters constrained

Δρmax = 2.11 e Å−3

Δρmin = −2.87 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I. DOI: 10.1107/S1600536810046763/hy2375sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810046763/hy2375Isup2.hkl

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

[ZnI2(C12H12N2)(C2H6OS)]	F(000) = 1104
Mr = 581.56	Dx = 1.986 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 21034 reflections
a = 8.6173 (7) Å	θ = 2.4–29.2°
b = 15.5424 (11) Å	µ = 4.54 mm−1
c = 14.8976 (10) Å	T = 298 K
β = 102.908 (6)°	Block, colorless
V = 1944.9 (3) Å3	0.40 × 0.20 × 0.10 mm
Z = 4

Bruker APEX CCD diffractometer	5243 independent reflections
Radiation source: fine-focus sealed tube	4246 reflections with I > 2σ(I)
graphite	Rint = 0.113
φ and ω scans	θmax = 29.2°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
Tmin = 0.350, Tmax = 0.636	k = −21→21
21034 measured reflections	l = −20→19

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)] = 0.076	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.202	H-atom parameters constrained
S = 1.20	w = 1/[σ2(Fo2) + (0.1105P)2 + 1.119P] where P = (Fo2 + 2Fc2)/3
5243 reflections	(Δ/σ)max = 0.006
191 parameters	Δρmax = 2.11 e Å−3
0 restraints	Δρmin = −2.87 e Å−3

	x	y	z	Uiso*/Ueq
C1	0.3959 (9)	0.0849 (4)	0.5994 (5)	0.0499 (15)
H1	0.4491	0.1110	0.6537	0.060*
C2	0.4035 (10)	0.1229 (5)	0.5175 (5)	0.0558 (18)
H2	0.4613	0.1734	0.5171	0.067*
C3	0.3249 (8)	0.0859 (4)	0.4355 (5)	0.0434 (13)
C4	0.3297 (12)	0.1243 (6)	0.3445 (5)	0.060 (2)
H4C	0.2999	0.0816	0.2972	0.072*
H4B	0.4356	0.1442	0.3456	0.072*
H4A	0.2568	0.1718	0.3320	0.072*
C5	0.2391 (8)	0.0114 (4)	0.4415 (4)	0.0404 (12)
H5	0.1819	−0.0146	0.3880	0.049*
C6	0.2382 (7)	−0.0246 (4)	0.5263 (4)	0.0348 (11)
C7	0.1490 (7)	−0.1048 (4)	0.5361 (4)	0.0371 (11)
C8	0.0708 (8)	−0.1531 (5)	0.4614 (4)	0.0444 (13)
H8	0.0759	−0.1363	0.4022	0.053*
C9	−0.0137 (9)	−0.2252 (5)	0.4731 (5)	0.0520 (16)
C10	−0.0965 (13)	−0.2786 (6)	0.3928 (7)	0.072 (2)
H10C	−0.1468	−0.3269	0.4146	0.087*
H10B	−0.0202	−0.2987	0.3595	0.087*
H10A	−0.1755	−0.2443	0.3528	0.087*
C11	−0.0155 (10)	−0.2477 (5)	0.5633 (6)	0.0578 (18)
H11	−0.0723	−0.2957	0.5749	0.069*
C12	0.0667 (11)	−0.1988 (5)	0.6351 (5)	0.0563 (18)
H12	0.0660	−0.2157	0.6949	0.068*
C13	0.573 (3)	0.1599 (8)	0.8800 (9)	0.148 (9)
H13A	0.4826	0.1882	0.8428	0.178*
H13B	0.6632	0.1665	0.8523	0.178*
H13C	0.5975	0.1849	0.9404	0.178*
C14	0.7238 (12)	0.0134 (10)	0.9372 (7)	0.093 (4)
H14A	0.7977	0.0373	0.9044	0.112*
H14B	0.7258	−0.0482	0.9334	0.112*
H14C	0.7531	0.0307	1.0006	0.112*
N1	0.3148 (6)	0.0114 (3)	0.6051 (3)	0.0390 (10)
N2	0.1480 (7)	−0.1279 (4)	0.6227 (3)	0.0408 (11)
O1	0.4955 (6)	0.0209 (4)	0.7891 (3)	0.0512 (11)
Zn1	0.28482 (9)	−0.04667 (5)	0.72994 (5)	0.0401 (2)
I1	0.07682 (6)	0.04536 (4)	0.79226 (3)	0.05824 (19)
I2	0.37974 (8)	−0.18094 (4)	0.84331 (4)	0.0642 (2)
S1	0.5317 (2)	0.05061 (13)	0.88831 (11)	0.0482 (4)

	U11	U22	U33	U12	U13	U23
C1	0.057 (4)	0.047 (3)	0.043 (3)	−0.012 (3)	0.005 (3)	−0.002 (3)
C2	0.070 (5)	0.052 (4)	0.046 (4)	−0.016 (3)	0.013 (3)	0.003 (3)
C3	0.045 (3)	0.046 (3)	0.039 (3)	−0.005 (3)	0.010 (2)	0.005 (2)
C4	0.079 (5)	0.064 (4)	0.042 (4)	−0.011 (4)	0.021 (4)	0.012 (3)
C5	0.046 (3)	0.049 (3)	0.027 (2)	0.001 (3)	0.009 (2)	0.000 (2)
C6	0.035 (3)	0.040 (3)	0.030 (2)	−0.001 (2)	0.009 (2)	−0.002 (2)
C7	0.038 (3)	0.044 (3)	0.030 (3)	0.001 (2)	0.009 (2)	0.004 (2)
C8	0.046 (3)	0.052 (3)	0.036 (3)	−0.009 (3)	0.012 (2)	−0.001 (3)
C9	0.050 (4)	0.057 (4)	0.049 (4)	−0.012 (3)	0.009 (3)	0.001 (3)
C10	0.075 (6)	0.073 (5)	0.068 (5)	−0.025 (5)	0.014 (4)	−0.009 (4)
C11	0.058 (4)	0.052 (4)	0.064 (5)	−0.010 (3)	0.016 (3)	0.012 (3)
C12	0.065 (5)	0.057 (4)	0.048 (4)	−0.007 (3)	0.014 (3)	0.018 (3)
C13	0.29 (3)	0.070 (7)	0.058 (6)	−0.031 (11)	−0.023 (10)	−0.004 (5)
C14	0.048 (4)	0.171 (12)	0.055 (5)	0.020 (6)	0.000 (4)	−0.011 (7)
N1	0.038 (2)	0.046 (3)	0.032 (2)	−0.004 (2)	0.0059 (19)	0.000 (2)
N2	0.041 (3)	0.051 (3)	0.031 (2)	−0.002 (2)	0.0088 (19)	0.006 (2)
O1	0.045 (2)	0.078 (3)	0.030 (2)	−0.008 (2)	0.0059 (18)	−0.003 (2)
Zn1	0.0420 (4)	0.0511 (4)	0.0273 (3)	0.0043 (3)	0.0079 (3)	0.0021 (3)
I1	0.0498 (3)	0.0841 (4)	0.0397 (3)	0.0204 (2)	0.00761 (19)	−0.0118 (2)
I2	0.0731 (4)	0.0624 (3)	0.0512 (3)	0.0118 (2)	0.0009 (2)	0.0195 (2)
S1	0.0445 (8)	0.0693 (11)	0.0297 (7)	0.0026 (7)	0.0062 (6)	0.0014 (6)

C1—N1	1.352 (9)	C10—H10B	0.9600
C1—C2	1.370 (10)	C10—H10A	0.9600
C1—H1	0.9300	C11—C12	1.372 (12)
C2—C3	1.383 (10)	C11—H11	0.9300
C2—H2	0.9300	C12—N2	1.341 (9)
C3—C5	1.388 (9)	C12—H12	0.9300
C3—C4	1.490 (9)	C13—S1	1.746 (12)
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	1.384 (8)	C14—S1	1.751 (10)
C5—H5	0.9300	C14—H14A	0.9600
C6—N1	1.334 (7)	C14—H14B	0.9600
C6—C7	1.488 (8)	C14—H14C	0.9600
C7—N2	1.341 (7)	Zn1—N1	2.135 (5)
C7—C8	1.387 (9)	Zn1—N2	2.167 (6)
C8—C9	1.368 (10)	O1—S1	1.513 (5)
C8—H8	0.9300	Zn1—O1	2.112 (5)
C9—C11	1.392 (11)	Zn1—I1	2.6199 (9)
C9—C10	1.498 (12)	Zn1—I2	2.6944 (9)
C10—H10C	0.9600
N1—C1—C2	123.3 (7)	C12—C11—H11	120.0
N1—C1—H1	118.3	C9—C11—H11	120.0
C2—C1—H1	118.3	N2—C12—C11	122.8 (7)
C1—C2—C3	119.7 (7)	N2—C12—H12	118.6
C1—C2—H2	120.2	C11—C12—H12	118.6
C3—C2—H2	120.2	S1—C13—H13A	109.5
C2—C3—C5	117.0 (6)	S1—C13—H13B	109.5
C2—C3—C4	122.0 (6)	H13A—C13—H13B	109.5
C5—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—H14A	109.5
C3—C4—H4A	109.5	S1—C14—H14B	109.5
H4C—C4—H4A	109.5	H14A—C14—H14B	109.5
H4B—C4—H4A	109.5	S1—C14—H14C	109.5
C6—C5—C3	120.5 (6)	H14A—C14—H14C	109.5
C6—C5—H5	119.7	H14B—C14—H14C	109.5
C3—C5—H5	119.7	C6—N1—C1	117.4 (5)
N1—C6—C5	122.1 (6)	C6—N1—Zn1	117.2 (4)
N1—C6—C7	115.5 (5)	C1—N1—Zn1	125.2 (4)
C5—C6—C7	122.4 (5)	C12—N2—C7	117.9 (6)
N2—C7—C8	121.4 (6)	C12—N2—Zn1	126.3 (5)
N2—C7—C6	115.7 (5)	C7—N2—Zn1	115.7 (4)
C8—C7—C6	123.0 (5)	S1—O1—Zn1	122.0 (3)
C9—C8—C7	121.3 (6)	O1—Zn1—N1	83.89 (19)
C9—C8—H8	119.4	O1—Zn1—N2	150.80 (19)
C7—C8—H8	119.4	N1—Zn1—N2	75.84 (19)
C8—C9—C11	116.7 (7)	O1—Zn1—I1	99.96 (15)
C8—C9—C10	121.6 (7)	N1—Zn1—I1	107.68 (15)
C11—C9—C10	121.8 (7)	N2—Zn1—I1	106.06 (15)
C9—C10—H10C	109.5	O1—Zn1—I2	90.64 (15)
C9—C10—H10B	109.5	N1—Zn1—I2	142.63 (15)
H10C—C10—H10B	109.5	N2—Zn1—I2	92.86 (14)
C9—C10—H10A	109.5	I1—Zn1—I2	109.67 (3)
H10C—C10—H10A	109.5	O1—S1—C13	103.2 (5)
H10B—C10—H10A	109.5	O1—S1—C14	106.0 (4)
C12—C11—C9	119.9 (7)	C13—S1—C14	99.2 (9)
N1—C1—C2—C3	0.3 (13)	C8—C7—N2—C12	−1.0 (10)
C1—C2—C3—C5	0.9 (12)	C6—C7—N2—C12	178.8 (6)
C1—C2—C3—C4	−179.7 (8)	C8—C7—N2—Zn1	177.7 (5)
C2—C3—C5—C6	−1.9 (10)	C6—C7—N2—Zn1	−2.6 (7)
C4—C3—C5—C6	178.7 (7)	S1—O1—Zn1—N1	151.4 (4)
C3—C5—C6—N1	1.8 (10)	S1—O1—Zn1—N2	−162.7 (3)
C3—C5—C6—C7	−179.5 (6)	S1—O1—Zn1—I1	44.4 (4)
N1—C6—C7—N2	4.2 (8)	S1—O1—Zn1—I2	−65.7 (4)
C5—C6—C7—N2	−174.5 (6)	C6—N1—Zn1—O1	160.7 (5)
N1—C6—C7—C8	−176.1 (6)	C1—N1—Zn1—O1	−24.2 (6)
C5—C6—C7—C8	5.2 (10)	C6—N1—Zn1—N2	1.9 (4)
N2—C7—C8—C9	1.6 (11)	C1—N1—Zn1—N2	177.0 (6)
C6—C7—C8—C9	−178.1 (7)	C6—N1—Zn1—I1	−100.8 (4)
C7—C8—C9—C11	−0.6 (12)	C1—N1—Zn1—I1	74.3 (6)
C7—C8—C9—C10	−179.1 (8)	C6—N1—Zn1—I2	77.7 (5)
C8—C9—C11—C12	−0.8 (13)	C1—N1—Zn1—I2	−107.2 (6)
C10—C9—C11—C12	177.6 (9)	C12—N2—Zn1—O1	131.6 (6)
C9—C11—C12—N2	1.5 (14)	C7—N2—Zn1—O1	−46.9 (7)
C5—C6—N1—C1	−0.5 (9)	C12—N2—Zn1—N1	179.0 (7)
C7—C6—N1—C1	−179.3 (6)	C7—N2—Zn1—N1	0.5 (4)
C5—C6—N1—Zn1	174.9 (5)	C12—N2—Zn1—I1	−76.3 (6)
C7—C6—N1—Zn1	−3.8 (7)	C7—N2—Zn1—I1	105.2 (4)
C2—C1—N1—C6	−0.5 (11)	C12—N2—Zn1—I2	35.1 (6)
C2—C1—N1—Zn1	−175.6 (6)	C7—N2—Zn1—I2	−143.4 (4)
C11—C12—N2—C7	−0.5 (12)	Zn1—O1—S1—C13	−127.7 (9)
C11—C12—N2—Zn1	−179.0 (6)	Zn1—O1—S1—C14	128.5 (6)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O1	0.93	2.41	2.938 (9)	116

Table 1

Selected bond lengths (Å)

Zn1—N1	2.135 (5)
Zn1—N2	2.167 (6)
Zn1—O1	2.112 (5)
Zn1—I1	2.6199 (9)
Zn1—I2	2.6944 (9)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯O1	0.93	2.41	2.938 (9)	116