(2,2'-Bipyridine-κN,N')dibromido(dimethyl sulfoxide-κO)zinc(II).

In the mol-ecule of the title compound, [ZnBr(2)(C(10)H(8)N(2))(C(2)H(6)OS)], the Zn(II) atom is five-coordinated in a distorted trigonal-bipyramidal configuration by two N atoms from one 2,2'-bipyridine, one O atom from one dimethyl-sulfoxide molecule and two Br atoms. Inter-molecular π-π stacking between parallel pyridine rings [face-to-face distance 3.32 (4) Å] and C-H⋯Br and C-H⋯O hydrogen-bonding interactions are present in the crystal structure.

Related literature

For related structures, see: Ahmadi et al. (2008 ▶); Alizadeh, Kalateh, Ebadi et al. (2009 ▶); Alizadeh, Kalateh, Khoshtarkib et al. (2009 ▶); Alizadeh, Khoshtarkib et al. (2009 ▶); Blake et al. (2007 ▶); Khan & Tuck (1984 ▶); Marjani et al. (2007 ▶); Khalighi et al. (2008 ▶).

Experimental

Crystal data

[ZnBr2(C10n class="Species">H8N2)(C2H6OS)]

M = 459.51

Monoclinic,

a = 9.4802 (10) Å

b = 8.3449 (7) Å

c = 19.989 (2) Å

β = 95.185 (8)°

V = 1574.9 (3) Å3

Z = 4

Mo Kα radiation

μ = 6.76 mm−1

T = 298 K

0.30 × 0.25 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.148, T max = 0.260

12674 measured reflections

4245 independent reflections

3229 reflections with I > 2σ(I)

R int = 0.078

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.140

S = 1.13

4245 reflections

175 parameters

H-atom parameters constrained

Δρmax = 1.08 e Å−3

Δρmin = −1.46 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT; 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/S1600536810017551/xu2761sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810017551/xu2761Isup2.hkl

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

[ZnBr2(C10H8N2)(C2H6OS)]	F(000) = 896
Mr = 459.51	Dx = 1.938 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 653 reflections
a = 9.4802 (10) Å	θ = 2.1–29.2°
b = 8.3449 (7) Å	µ = 6.76 mm−1
c = 19.989 (2) Å	T = 298 K
β = 95.185 (8)°	Block, colorless
V = 1574.9 (3) Å3	0.30 × 0.25 × 0.20 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	4245 independent reflections
Radiation source: fine-focus sealed tube	3229 reflections with I > 2σ(I)
graphite	Rint = 0.078
φ and ω scans	θmax = 29.2°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −12→12
Tmin = 0.148, Tmax = 0.260	k = −11→11
12674 measured reflections	l = −27→25

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)] = 0.058	H-atom parameters constrained
wR(F2) = 0.140	w = 1/[σ2(Fo2) + (0.0602P)2 + 1.8278P] where P = (Fo2 + 2Fc2)/3
S = 1.13	(Δ/σ)max = 0.005
4245 reflections	Δρmax = 1.08 e Å−3
175 parameters	Δρmin = −1.46 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: 0.0087 (7)

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	0.5556 (5)	0.1151 (7)	0.3831 (3)	0.0377 (10)
H1	0.5286	0.0980	0.3378	0.045*
C2	0.6783 (5)	0.0424 (7)	0.4117 (3)	0.0425 (12)
H2	0.7333	−0.0208	0.3859	0.051*
C3	0.7166 (6)	0.0660 (7)	0.4788 (3)	0.0462 (13)
H3	0.7982	0.0185	0.4992	0.055*
C4	0.6335 (5)	0.1603 (6)	0.5155 (3)	0.0383 (10)
H4	0.6581	0.1772	0.5611	0.046*
C5	0.5129 (5)	0.2297 (6)	0.4840 (2)	0.0295 (9)
C6	0.4154 (5)	0.3323 (6)	0.5190 (2)	0.0311 (9)
C7	0.4311 (6)	0.3600 (7)	0.5883 (2)	0.0406 (11)
H7	0.5056	0.3137	0.6150	0.049*
C8	0.3346 (6)	0.4570 (7)	0.6166 (3)	0.0432 (12)
H8	0.3433	0.4771	0.6625	0.052*
C9	0.2254 (5)	0.5234 (7)	0.5759 (3)	0.0422 (12)
H9	0.1589	0.5889	0.5939	0.051*
C10	0.2162 (5)	0.4915 (7)	0.5085 (3)	0.0395 (11)
H10	0.1421	0.5366	0.4812	0.047*
C11	0.2234 (7)	0.7783 (10)	0.2635 (4)	0.0621 (18)
H11A	0.3167	0.7412	0.2564	0.075*
H11B	0.2302	0.8683	0.2935	0.075*
H11C	0.1750	0.8099	0.2213	0.075*
C12	−0.0109 (6)	0.7414 (10)	0.3256 (4)	0.0650 (19)
H12A	0.0281	0.8281	0.3529	0.078*
H12B	−0.0698	0.6765	0.3514	0.078*
H12C	−0.0665	0.7838	0.2872	0.078*
N1	0.4750 (4)	0.2084 (5)	0.41813 (19)	0.0324 (8)
N2	0.3090 (4)	0.3984 (5)	0.48005 (19)	0.0324 (8)
O1	0.2163 (4)	0.5774 (5)	0.36384 (18)	0.0440 (9)
Zn1	0.29167 (5)	0.33824 (7)	0.37552 (3)	0.03244 (16)
Br1	0.37506 (6)	0.34269 (8)	0.26199 (3)	0.04918 (19)
Br2	0.07887 (6)	0.17861 (8)	0.37356 (3)	0.05171 (19)
S1	0.12833 (14)	0.62307 (17)	0.29876 (7)	0.0413 (3)

	U11	U22	U33	U12	U13	U23
C1	0.040 (2)	0.040 (3)	0.033 (2)	0.006 (2)	0.0043 (19)	−0.001 (2)
C2	0.042 (3)	0.038 (3)	0.049 (3)	0.009 (2)	0.012 (2)	−0.001 (2)
C3	0.041 (3)	0.044 (3)	0.052 (3)	0.009 (2)	−0.002 (2)	0.008 (3)
C4	0.038 (2)	0.041 (3)	0.035 (2)	−0.001 (2)	−0.0051 (18)	0.004 (2)
C5	0.032 (2)	0.028 (2)	0.028 (2)	−0.0061 (17)	0.0007 (16)	0.0022 (17)
C6	0.0297 (19)	0.031 (2)	0.032 (2)	−0.0062 (17)	0.0025 (16)	−0.0013 (19)
C7	0.043 (3)	0.047 (3)	0.031 (2)	−0.006 (2)	−0.0026 (19)	−0.001 (2)
C8	0.052 (3)	0.049 (3)	0.029 (2)	−0.008 (2)	0.008 (2)	−0.003 (2)
C9	0.046 (3)	0.040 (3)	0.043 (3)	0.000 (2)	0.018 (2)	−0.001 (2)
C10	0.037 (2)	0.043 (3)	0.039 (2)	0.005 (2)	0.0079 (19)	0.004 (2)
C11	0.047 (3)	0.080 (5)	0.060 (4)	−0.005 (3)	0.010 (3)	0.026 (4)
C12	0.040 (3)	0.071 (5)	0.086 (5)	0.006 (3)	0.014 (3)	0.022 (4)
N1	0.0333 (18)	0.034 (2)	0.0299 (18)	0.0003 (15)	0.0015 (14)	0.0026 (16)
N2	0.0278 (17)	0.039 (2)	0.0309 (18)	−0.0022 (15)	0.0029 (14)	−0.0005 (17)
O1	0.053 (2)	0.041 (2)	0.0352 (18)	0.0093 (16)	−0.0089 (15)	0.0020 (16)
Zn1	0.0303 (3)	0.0378 (3)	0.0285 (3)	0.0010 (2)	−0.00125 (19)	0.0005 (2)
Br1	0.0467 (3)	0.0704 (4)	0.0309 (2)	0.0102 (3)	0.0059 (2)	0.0055 (3)
Br2	0.0373 (3)	0.0562 (4)	0.0604 (4)	−0.0122 (2)	−0.0025 (2)	−0.0009 (3)
S1	0.0409 (6)	0.0409 (7)	0.0397 (6)	0.0015 (5)	−0.0084 (5)	0.0036 (5)

C1—N1	1.333 (6)	C9—H9	0.9300
C1—C2	1.388 (7)	C10—N2	1.338 (6)
C1—H1	0.9300	C10—H10	0.9300
C2—C3	1.372 (8)	C11—S1	1.761 (7)
C2—H2	0.9300	C11—H11A	0.9600
C3—C4	1.372 (8)	C11—H11B	0.9600
C3—H3	0.9300	C11—H11C	0.9600
C4—C5	1.382 (6)	C12—S1	1.770 (7)
C4—H4	0.9300	C12—H12A	0.9600
C5—N1	1.345 (6)	C12—H12B	0.9600
C5—C6	1.480 (6)	C12—H12C	0.9600
C6—N2	1.336 (6)	Zn1—N1	2.157 (4)
C6—C7	1.401 (6)	Zn1—N2	2.141 (4)
C7—C8	1.380 (8)	S1—O1	1.529 (4)
C7—H7	0.9300	Zn1—O1	2.125 (4)
C8—C9	1.374 (8)	Zn1—Br1	2.4701 (8)
C8—H8	0.9300	Zn1—Br2	2.4148 (8)
C9—C10	1.369 (7)
N1—C1—C2	122.6 (5)	S1—C11—H11B	109.5
N1—C1—H1	118.7	H11A—C11—H11B	109.5
C2—C1—H1	118.7	S1—C11—H11C	109.5
C3—C2—C1	118.5 (5)	H11A—C11—H11C	109.5
C3—C2—H2	120.7	H11B—C11—H11C	109.5
C1—C2—H2	120.7	S1—C12—H12A	109.5
C2—C3—C4	119.4 (5)	S1—C12—H12B	109.5
C2—C3—H3	120.3	H12A—C12—H12B	109.5
C4—C3—H3	120.3	S1—C12—H12C	109.5
C3—C4—C5	119.2 (5)	H12A—C12—H12C	109.5
C3—C4—H4	120.4	H12B—C12—H12C	109.5
C5—C4—H4	120.4	C1—N1—C5	118.4 (4)
N1—C5—C4	121.8 (5)	C1—N1—Zn1	124.5 (3)
N1—C5—C6	114.5 (4)	C5—N1—Zn1	117.1 (3)
C4—C5—C6	123.6 (4)	C6—N2—C10	118.9 (4)
N2—C6—C7	121.0 (4)	C6—N2—Zn1	117.3 (3)
N2—C6—C5	115.8 (4)	C10—N2—Zn1	123.7 (3)
C7—C6—C5	123.2 (4)	S1—O1—Zn1	118.7 (2)
C8—C7—C6	119.1 (5)	O1—Zn1—N2	83.24 (15)
C8—C7—H7	120.4	O1—Zn1—N1	139.98 (15)
C6—C7—H7	120.4	N2—Zn1—N1	75.19 (15)
C9—C8—C7	119.1 (5)	O1—Zn1—Br2	104.13 (11)
C9—C8—H8	120.4	N2—Zn1—Br2	97.80 (11)
C7—C8—H8	120.4	N1—Zn1—Br2	111.81 (11)
C10—C9—C8	118.8 (5)	O1—Zn1—Br1	90.99 (11)
C10—C9—H9	120.6	N2—Zn1—Br1	152.93 (11)
C8—C9—H9	120.6	N1—Zn1—Br1	93.27 (11)
N2—C10—C9	123.1 (5)	Br2—Zn1—Br1	109.25 (3)
N2—C10—H10	118.5	O1—S1—C11	105.3 (3)
C9—C10—H10	118.5	O1—S1—C12	104.2 (3)
S1—C11—H11A	109.5	C11—S1—C12	97.7 (4)
N1—C1—C2—C3	1.0 (9)	C9—C10—N2—C6	0.4 (8)
C1—C2—C3—C4	−0.2 (9)	C9—C10—N2—Zn1	177.1 (4)
C2—C3—C4—C5	−0.1 (8)	S1—O1—Zn1—N2	−159.5 (3)
C3—C4—C5—N1	−0.5 (8)	S1—O1—Zn1—N1	143.3 (2)
C3—C4—C5—C6	179.5 (5)	S1—O1—Zn1—Br2	−63.2 (3)
N1—C5—C6—N2	−4.3 (6)	S1—O1—Zn1—Br1	47.0 (3)
C4—C5—C6—N2	175.7 (4)	C6—N2—Zn1—O1	−146.3 (4)
N1—C5—C6—C7	175.5 (4)	C10—N2—Zn1—O1	36.9 (4)
C4—C5—C6—C7	−4.5 (7)	C6—N2—Zn1—N1	−0.3 (3)
N2—C6—C7—C8	0.1 (8)	C10—N2—Zn1—N1	−177.1 (4)
C5—C6—C7—C8	−179.7 (5)	C6—N2—Zn1—Br2	110.3 (3)
C6—C7—C8—C9	0.2 (8)	C10—N2—Zn1—Br2	−66.5 (4)
C7—C8—C9—C10	−0.2 (8)	C6—N2—Zn1—Br1	−67.5 (5)
C8—C9—C10—N2	−0.1 (8)	C10—N2—Zn1—Br1	115.7 (4)
C2—C1—N1—C5	−1.5 (8)	C1—N1—Zn1—O1	−119.4 (4)
C2—C1—N1—Zn1	175.5 (4)	C5—N1—Zn1—O1	57.6 (4)
C4—C5—N1—C1	1.2 (7)	C1—N1—Zn1—N2	−179.1 (4)
C6—C5—N1—C1	−178.8 (4)	C5—N1—Zn1—N2	−2.2 (3)
C4—C5—N1—Zn1	−175.9 (4)	C1—N1—Zn1—Br2	88.3 (4)
C6—C5—N1—Zn1	4.0 (5)	C5—N1—Zn1—Br2	−94.7 (3)
C7—C6—N2—C10	−0.4 (7)	C1—N1—Zn1—Br1	−24.0 (4)
C5—C6—N2—C10	179.4 (4)	C5—N1—Zn1—Br1	153.0 (3)
C7—C6—N2—Zn1	−177.3 (4)	Zn1—O1—S1—C11	−120.4 (4)
C5—C6—N2—Zn1	2.5 (5)	Zn1—O1—S1—C12	137.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···Br1	0.93	2.86	3.413 (6)	119
C10—H10···O1	0.93	2.53	2.979 (7)	110

Table 1

Selected bond lengths (Å)

Zn1—N1	2.157 (4)
Zn1—N2	2.141 (4)
Zn1—O1	2.125 (4)
Zn1—Br1	2.4701 (8)
Zn1—Br2	2.4148 (8)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯Br1	0.93	2.86	3.413 (6)	119
C10—H10⋯O1	0.93	2.53	2.979 (7)	110