4,4'-Bipyridine-1,1'-diium bis-(1,3-benzo-thia-zole-2-thiol-ate).

In the title salt, C10H10N2(2+)·2C7H4NS2(-), the complete 4,4'-bipyridine-1,1'-diium dication is generated by a center of symmetry. In the crystal, N-H⋯N hydrogen bonds are observed between the cations and anions.

Related literature

For ligands based on 2-mercaptobenzothia­zole in coordination chemistry, see: Chen et al. (2010 ▶) and for ligands based on 4,4′- bipyridine, see: Biradha et al. (1999 ▶); Ren et al. (2004 ▶); Tao et al. (2000 ▶); Tong et al. (2000 ▶); Xu et al. (2012 ▶). For a related structure, see: Deng et al. (2005 ▶).

Experimental

Crystal data

C10H10N2 2+·2C7H4NS2 −

M = 490.66

Monoclinic,

a = 14.3909 (13) Å

b = 5.6670 (4) Å

c = 15.5471 (14) Å

β = 109.023 (2)°

V = 1198.67 (17) Å3

Z = 2

Mo Kα radiation

μ = 0.42 mm−1

T = 298 K

0.32 × 0.30 × 0.26 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.878, T max = 0.900

5663 measured reflections

2116 independent reflections

990 reflections with I > 2σ(I)

R int = 0.055

Refinement

R[F 2 > 2σ(F 2)] = 0.060

wR(F 2) = 0.203

S = 1.04

2116 reflections

145 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.26 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT-Plus (Bruker, 2007 ▶); data reduction: SAINT-Plus; 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.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812047058/jj2151sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812047058/jj2151Isup2.hkl

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

C10H10N22+·2C7H4NS2−	F(000) = 508
Mr = 490.66	Dx = 1.359 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1198 reflections
a = 14.3909 (13) Å	θ = 2.7–20.7°
b = 5.6670 (4) Å	µ = 0.42 mm−1
c = 15.5471 (14) Å	T = 298 K
β = 109.023 (2)°	Block, colorless
V = 1198.67 (17) Å3	0.32 × 0.30 × 0.26 mm
Z = 2

Bruker SMART CCD area-detector diffractometer	2116 independent reflections
Radiation source: fine-focus sealed tube	990 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.055
phi and ω scans	θmax = 25.0°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −17→11
Tmin = 0.878, Tmax = 0.900	k = −6→6
5663 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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.203	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0797P)2 + 0.6601P] where P = (Fo2 + 2Fc2)/3
2116 reflections	(Δ/σ)max < 0.001
145 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.26 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
N1	0.2335 (3)	0.3414 (7)	0.7956 (2)	0.0629 (11)
N2	0.6509 (3)	0.4638 (7)	0.6145 (3)	0.0700 (11)
H2	0.6875	0.5792	0.6419	0.084*
S1	0.16856 (12)	0.6851 (3)	0.68804 (10)	0.1018 (7)
S2	0.30080 (16)	0.3128 (4)	0.65559 (11)	0.1352 (9)
C1	0.2387 (4)	0.4264 (10)	0.7171 (3)	0.0812 (16)
C2	0.1755 (3)	0.4737 (9)	0.8346 (3)	0.0586 (12)
C3	0.1353 (4)	0.6727 (10)	0.7852 (3)	0.0720 (14)
C4	0.0782 (4)	0.8244 (11)	0.8160 (5)	0.102 (2)
H4	0.0515	0.9598	0.7835	0.122*
C5	0.0617 (5)	0.7703 (13)	0.8960 (6)	0.112 (2)
H5	0.0217	0.8680	0.9170	0.135*
C6	0.1030 (5)	0.5758 (13)	0.9448 (4)	0.0991 (19)
H6	0.0921	0.5448	0.9995	0.119*
C7	0.1601 (3)	0.4255 (9)	0.9152 (3)	0.0700 (14)
H7	0.1879	0.2929	0.9491	0.084*
C8	0.5934 (4)	0.3548 (11)	0.6502 (4)	0.0888 (18)
H8	0.5926	0.4038	0.7070	0.107*
C9	0.5343 (4)	0.1726 (11)	0.6091 (4)	0.0888 (17)
H9	0.4955	0.0979	0.6385	0.107*
C10	0.5317 (3)	0.0987 (8)	0.5244 (3)	0.0549 (12)
C11	0.5936 (4)	0.2124 (10)	0.4888 (3)	0.0843 (17)
H11	0.5967	0.1676	0.4322	0.101*
C12	0.6507 (4)	0.3907 (11)	0.5350 (4)	0.0914 (19)
H12	0.6923	0.4653	0.5086	0.110*

	U11	U22	U33	U12	U13	U23
N1	0.068 (2)	0.077 (3)	0.046 (2)	−0.008 (2)	0.0210 (19)	0.002 (2)
N2	0.060 (2)	0.070 (3)	0.072 (3)	−0.015 (2)	0.010 (2)	−0.002 (2)
S1	0.1082 (12)	0.1031 (13)	0.0740 (9)	−0.0164 (10)	0.0019 (8)	0.0351 (9)
S2	0.1740 (19)	0.177 (2)	0.0824 (11)	−0.0039 (16)	0.0806 (12)	0.0087 (12)
C1	0.086 (4)	0.105 (5)	0.051 (3)	−0.020 (3)	0.020 (3)	0.013 (3)
C2	0.057 (3)	0.059 (3)	0.054 (3)	−0.004 (2)	0.010 (2)	0.001 (2)
C3	0.063 (3)	0.058 (3)	0.077 (3)	−0.009 (3)	−0.002 (3)	0.005 (3)
C4	0.074 (4)	0.061 (4)	0.141 (6)	0.008 (3)	−0.004 (4)	0.000 (4)
C5	0.091 (5)	0.094 (6)	0.146 (7)	0.011 (4)	0.031 (5)	−0.035 (5)
C6	0.103 (5)	0.105 (5)	0.095 (4)	0.012 (4)	0.040 (4)	−0.018 (4)
C7	0.076 (3)	0.069 (3)	0.068 (3)	0.005 (3)	0.027 (3)	−0.004 (3)
C8	0.089 (4)	0.108 (5)	0.077 (4)	−0.031 (4)	0.038 (3)	−0.019 (3)
C9	0.085 (4)	0.116 (5)	0.081 (4)	−0.027 (4)	0.049 (3)	−0.015 (4)
C10	0.044 (3)	0.061 (3)	0.057 (3)	0.004 (2)	0.013 (2)	0.011 (2)
C11	0.099 (4)	0.103 (4)	0.054 (3)	−0.035 (4)	0.029 (3)	−0.007 (3)
C12	0.109 (4)	0.112 (5)	0.058 (3)	−0.040 (4)	0.033 (3)	0.001 (3)

N1—C1	1.337 (5)	C5—H5	0.9300
N1—C2	1.399 (5)	C6—C7	1.363 (7)
N2—C8	1.294 (6)	C6—H6	0.9300
N2—C12	1.303 (6)	C7—H7	0.9300
N2—H2	0.8600	C8—C9	1.358 (7)
S1—C3	1.728 (6)	C8—H8	0.9300
S1—C1	1.754 (6)	C9—C10	1.371 (6)
S2—C1	1.638 (6)	C9—H9	0.9300
C2—C7	1.370 (6)	C10—C11	1.355 (6)
C2—C3	1.381 (6)	C10—C10i	1.487 (8)
C3—C4	1.378 (8)	C11—C12	1.352 (7)
C4—C5	1.375 (9)	C11—H11	0.9300
C4—H4	0.9300	C12—H12	0.9300
C5—C6	1.361 (9)
C1—N1—C2	115.0 (4)	C5—C6—H6	119.3
C8—N2—C12	116.8 (5)	C7—C6—H6	119.3
C8—N2—H2	121.6	C6—C7—C2	118.6 (5)
C12—N2—H2	121.6	C6—C7—H7	120.7
C3—S1—C1	92.4 (3)	C2—C7—H7	120.7
N1—C1—S2	126.5 (5)	N2—C8—C9	123.5 (5)
N1—C1—S1	109.7 (4)	N2—C8—H8	118.3
S2—C1—S1	123.8 (3)	C9—C8—H8	118.3
C7—C2—C3	120.6 (5)	C8—C9—C10	120.1 (5)
C7—C2—N1	126.0 (4)	C8—C9—H9	120.0
C3—C2—N1	113.4 (4)	C10—C9—H9	120.0
C4—C3—C2	120.3 (5)	C11—C10—C9	115.6 (4)
C4—C3—S1	130.1 (5)	C11—C10—C10i	121.7 (5)
C2—C3—S1	109.6 (4)	C9—C10—C10i	122.7 (5)
C5—C4—C3	118.3 (6)	C12—C11—C10	120.3 (5)
C5—C4—H4	120.9	C12—C11—H11	119.8
C3—C4—H4	120.9	C10—C11—H11	119.8
C6—C5—C4	120.8 (6)	N2—C12—C11	123.7 (5)
C6—C5—H5	119.6	N2—C12—H12	118.1
C4—C5—H5	119.6	C11—C12—H12	118.1
C5—C6—C7	121.3 (6)
C2—N1—C1—S2	179.6 (4)	C3—C4—C5—C6	1.9 (10)
C2—N1—C1—S1	0.0 (5)	C4—C5—C6—C7	−1.6 (10)
C3—S1—C1—N1	0.9 (4)	C5—C6—C7—C2	0.1 (8)
C3—S1—C1—S2	−178.8 (4)	C3—C2—C7—C6	1.0 (7)
C1—N1—C2—C7	−178.8 (4)	N1—C2—C7—C6	178.6 (5)
C1—N1—C2—C3	−1.1 (6)	C12—N2—C8—C9	−0.2 (8)
C7—C2—C3—C4	−0.6 (7)	N2—C8—C9—C10	−1.5 (9)
N1—C2—C3—C4	−178.5 (4)	C8—C9—C10—C11	2.4 (8)
C7—C2—C3—S1	179.5 (4)	C8—C9—C10—C10i	−179.7 (5)
N1—C2—C3—S1	1.7 (5)	C9—C10—C11—C12	−1.8 (8)
C1—S1—C3—C4	178.7 (5)	C10i—C10—C11—C12	−179.7 (5)
C1—S1—C3—C2	−1.5 (4)	C8—N2—C12—C11	0.9 (8)
C2—C3—C4—C5	−0.8 (8)	C10—C11—C12—N2	0.1 (9)
S1—C3—C4—C5	179.0 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···N1ii	0.86	1.93	2.790 (6)	178

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯N1i	0.86	1.93	2.790 (6)	178

Symmetry code: (i) .