Bis(2-methyl-1H-benzimidazol-3-ium) naphthalene-1,5-disulfonate.

The asymmetric unit of the title compound, 2C(8)H(9)N(2) (+)·C(10)H(6)O(6)S(2) (2-), contains a 2-methyl-benzimidazolium cation and one half of a naphthalene-1,5-disulfonate anion. The formula unit is generated by an inversion center. In the crystal, N-H⋯O hydrogen bonds link the components into chains along [001]. In addition, weak C-H⋯O hydrogen bonds and weak C-H⋯π inter-actions are observed. The methyl H atoms were refined as disordered over two sets of sites with equal occupancy.

Related literature

For general background to organic acids, see: Jin et al. (2012 ▶); Elder et al. (2010 ▶); Voogt & Blanch (2005 ▶); Wang et al. (2005 ▶); Zhang et al. (2005 ▶).

Experimental

Crystal data

2C8H9N2 +·C10H6O6S2 2−

M = 552.61

Triclinic,

a = 8.0360 (7) Å

b = 9.3969 (8) Å

c = 9.5101 (9) Å

α = 105.789 (1)°

β = 103.303 (1)°

γ = 106.497 (2)°

V = 624.75 (10) Å3

Z = 1

Mo Kα radiation

μ = 0.26 mm−1

T = 298 K

0.45 × 0.41 × 0.19 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T min = 0.888, T max = 0.951

3137 measured reflections

2169 independent reflections

1694 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.119

S = 1.05

2169 reflections

173 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.37 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812039396/lh5531sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812039396/lh5531Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812039396/lh5531Isup3.cml

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

2C8H9N2+·C10H6O6S22−	Z = 1
Mr = 552.61	F(000) = 288
Triclinic, P1	Dx = 1.469 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.0360 (7) Å	Cell parameters from 1471 reflections
b = 9.3969 (8) Å	θ = 2.4–28.0°
c = 9.5101 (9) Å	µ = 0.26 mm−1
α = 105.789 (1)°	T = 298 K
β = 103.303 (1)°	Block, colourless
γ = 106.497 (2)°	0.45 × 0.41 × 0.19 mm
V = 624.75 (10) Å3

Bruker SMART CCD diffractometer	2169 independent reflections
Radiation source: fine-focus sealed tube	1694 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
φ and ω scans	θmax = 25.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −9→9
Tmin = 0.888, Tmax = 0.951	k = −8→11
3137 measured reflections	l = −10→11

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)] = 0.043	H-atom parameters constrained
wR(F2) = 0.119	w = 1/[σ2(Fo2) + (0.0583P)2 + 0.1477P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
2169 reflections	Δρmax = 0.28 e Å−3
173 parameters	Δρmin = −0.37 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: 0.043 (6)

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	Occ. (<1)
N1	0.2089 (3)	0.0991 (2)	−0.0901 (2)	0.0390 (5)
H1	0.1838	0.1027	−0.1817	0.047*
N2	0.2562 (3)	0.1632 (2)	0.1561 (2)	0.0404 (5)
H2	0.2664	0.2148	0.2495	0.048*
O1	0.3057 (3)	0.2484 (2)	0.4604 (2)	0.0530 (6)
O2	0.1946 (3)	0.1418 (2)	0.6381 (2)	0.0447 (5)
O3	0.4010 (3)	0.4162 (2)	0.7288 (2)	0.0524 (5)
S1	0.25771 (8)	0.28337 (7)	0.60043 (6)	0.0330 (2)
C1	0.2166 (4)	0.2092 (3)	0.0356 (3)	0.0383 (6)
C2	0.2784 (3)	0.0185 (3)	0.1067 (3)	0.0354 (6)
C3	0.2475 (3)	−0.0230 (3)	−0.0511 (3)	0.0354 (6)
C4	0.2607 (4)	−0.1614 (3)	−0.1376 (3)	0.0436 (7)
H4	0.2379	−0.1902	−0.2438	0.052*
C5	0.3095 (4)	−0.2543 (3)	−0.0584 (3)	0.0495 (7)
H5	0.3195	−0.3484	−0.1125	0.059*
C6	0.3443 (4)	−0.2105 (3)	0.1010 (3)	0.0497 (7)
H6	0.3796	−0.2751	0.1506	0.060*
C7	0.3281 (4)	−0.0747 (3)	0.1870 (3)	0.0455 (7)
H7	0.3493	−0.0467	0.2929	0.055*
C8	0.1861 (4)	0.3582 (3)	0.0410 (4)	0.0552 (8)
H8A	0.1993	0.4176	0.1452	0.083*	0.50
H8B	0.0643	0.3332	−0.0263	0.083*	0.50
H8C	0.2749	0.4206	0.0077	0.083*	0.50
H8D	0.1597	0.3633	−0.0608	0.083*	0.50
H8E	0.2947	0.4477	0.1106	0.083*	0.50
H8F	0.0841	0.3603	0.0767	0.083*	0.50
C9	−0.0943 (3)	0.2568 (3)	0.5733 (3)	0.0356 (6)
H9	−0.1013	0.1681	0.6009	0.043*
C10	0.0652 (3)	0.3429 (3)	0.5591 (2)	0.0284 (5)
C11	0.0793 (3)	0.4782 (3)	0.5137 (2)	0.0275 (5)
C12	0.2405 (3)	0.5702 (3)	0.4963 (3)	0.0336 (6)
H12	0.3438	0.5427	0.5143	0.040*
C13	0.2477 (3)	0.6986 (3)	0.4535 (3)	0.0388 (6)
H13	0.3552	0.7570	0.4421	0.047*

	U11	U22	U33	U12	U13	U23
N1	0.0449 (13)	0.0439 (13)	0.0288 (11)	0.0159 (11)	0.0095 (10)	0.0171 (10)
N2	0.0476 (14)	0.0419 (13)	0.0294 (11)	0.0160 (11)	0.0130 (10)	0.0101 (10)
O1	0.0700 (14)	0.0829 (15)	0.0407 (11)	0.0547 (12)	0.0338 (10)	0.0335 (10)
O2	0.0573 (12)	0.0481 (11)	0.0447 (10)	0.0312 (10)	0.0162 (9)	0.0290 (9)
O3	0.0407 (11)	0.0512 (12)	0.0517 (12)	0.0217 (10)	−0.0051 (9)	0.0104 (9)
S1	0.0378 (4)	0.0441 (4)	0.0266 (3)	0.0251 (3)	0.0108 (3)	0.0166 (3)
C1	0.0355 (14)	0.0395 (15)	0.0375 (14)	0.0113 (12)	0.0089 (11)	0.0155 (12)
C2	0.0355 (14)	0.0385 (14)	0.0301 (13)	0.0099 (11)	0.0107 (11)	0.0136 (11)
C3	0.0368 (14)	0.0395 (14)	0.0319 (13)	0.0130 (12)	0.0118 (11)	0.0166 (11)
C4	0.0476 (17)	0.0448 (16)	0.0327 (13)	0.0148 (13)	0.0114 (12)	0.0095 (12)
C5	0.0500 (17)	0.0393 (16)	0.0580 (18)	0.0182 (14)	0.0170 (15)	0.0149 (14)
C6	0.0512 (18)	0.0452 (17)	0.0570 (18)	0.0174 (14)	0.0127 (14)	0.0298 (15)
C7	0.0518 (17)	0.0488 (17)	0.0369 (14)	0.0144 (14)	0.0125 (13)	0.0235 (13)
C8	0.0558 (19)	0.0448 (17)	0.0609 (19)	0.0220 (15)	0.0107 (16)	0.0169 (15)
C9	0.0424 (15)	0.0397 (14)	0.0350 (13)	0.0185 (12)	0.0167 (12)	0.0221 (12)
C10	0.0315 (13)	0.0366 (13)	0.0225 (11)	0.0181 (11)	0.0092 (10)	0.0126 (10)
C11	0.0318 (13)	0.0336 (13)	0.0214 (11)	0.0162 (11)	0.0100 (10)	0.0112 (10)
C12	0.0286 (13)	0.0467 (15)	0.0353 (13)	0.0211 (12)	0.0137 (11)	0.0194 (12)
C13	0.0329 (14)	0.0477 (15)	0.0463 (15)	0.0160 (12)	0.0194 (12)	0.0261 (13)

N1—C1	1.327 (3)	C6—H6	0.9300
N1—C3	1.390 (3)	C7—H7	0.9300
N1—H1	0.8600	C8—H8A	0.9600
N2—C1	1.335 (3)	C8—H8B	0.9600
N2—C2	1.389 (3)	C8—H8C	0.9600
N2—H2	0.8600	C8—H8D	0.9600
O1—S1	1.4491 (17)	C8—H8E	0.9600
O2—S1	1.4543 (17)	C8—H8F	0.9600
O3—S1	1.4427 (19)	C9—C10	1.366 (3)
S1—C10	1.786 (2)	C9—C13i	1.403 (4)
C1—C8	1.478 (4)	C9—H9	0.9300
C2—C3	1.386 (3)	C10—C11	1.433 (3)
C2—C7	1.390 (4)	C11—C12	1.413 (3)
C3—C4	1.384 (3)	C11—C11i	1.436 (4)
C4—C5	1.378 (4)	C12—C13	1.365 (3)
C4—H4	0.9300	C12—H12	0.9300
C5—C6	1.395 (4)	C13—C9i	1.403 (4)
C5—H5	0.9300	C13—H13	0.9300
C6—C7	1.375 (4)
C1—N1—C3	109.56 (19)	H8A—C8—H8B	109.5
C1—N1—H1	125.2	C1—C8—H8C	109.5
C3—N1—H1	125.2	H8A—C8—H8C	109.5
C1—N2—C2	109.1 (2)	H8B—C8—H8C	109.5
C1—N2—H2	125.5	C1—C8—H8D	109.5
C2—N2—H2	125.5	H8A—C8—H8D	141.1
O3—S1—O1	112.92 (13)	H8B—C8—H8D	56.3
O3—S1—O2	113.16 (11)	H8C—C8—H8D	56.3
O1—S1—O2	111.54 (11)	C1—C8—H8E	109.5
O3—S1—C10	106.00 (11)	H8A—C8—H8E	56.3
O1—S1—C10	106.50 (10)	H8B—C8—H8E	141.1
O2—S1—C10	106.07 (11)	H8C—C8—H8E	56.3
N1—C1—N2	108.8 (2)	H8D—C8—H8E	109.5
N1—C1—C8	125.5 (2)	C1—C8—H8F	109.5
N2—C1—C8	125.7 (2)	H8A—C8—H8F	56.3
C3—C2—N2	106.4 (2)	H8B—C8—H8F	56.3
C3—C2—C7	121.8 (2)	H8C—C8—H8F	141.1
N2—C2—C7	131.7 (2)	H8D—C8—H8F	109.5
C4—C3—C2	121.7 (2)	H8E—C8—H8F	109.5
C4—C3—N1	132.2 (2)	C10—C9—C13i	120.3 (2)
C2—C3—N1	106.1 (2)	C10—C9—H9	119.8
C5—C4—C3	116.6 (2)	C13i—C9—H9	119.8
C5—C4—H4	121.7	C9—C10—C11	121.2 (2)
C3—C4—H4	121.7	C9—C10—S1	118.13 (18)
C4—C5—C6	121.5 (3)	C11—C10—S1	120.63 (17)
C4—C5—H5	119.2	C12—C11—C10	123.4 (2)
C6—C5—H5	119.2	C12—C11—C11i	118.9 (2)
C7—C6—C5	122.0 (3)	C10—C11—C11i	117.7 (3)
C7—C6—H6	119.0	C13—C12—C11	121.3 (2)
C5—C6—H6	119.0	C13—C12—H12	119.4
C6—C7—C2	116.2 (2)	C11—C12—H12	119.4
C6—C7—H7	121.9	C12—C13—C9i	120.5 (2)
C2—C7—H7	121.9	C12—C13—H13	119.7
C1—C8—H8A	109.5	C9i—C13—H13	119.7
C1—C8—H8B	109.5
C3—N1—C1—N2	−1.0 (3)	C3—C2—C7—C6	−0.2 (4)
C3—N1—C1—C8	179.1 (3)	N2—C2—C7—C6	−177.4 (3)
C2—N2—C1—N1	1.1 (3)	C13i—C9—C10—C11	−1.3 (4)
C2—N2—C1—C8	−178.9 (3)	C13i—C9—C10—S1	178.19 (18)
C1—N2—C2—C3	−0.9 (3)	O3—S1—C10—C9	−118.6 (2)
C1—N2—C2—C7	176.6 (3)	O1—S1—C10—C9	120.9 (2)
N2—C2—C3—C4	179.3 (2)	O2—S1—C10—C9	2.0 (2)
C7—C2—C3—C4	1.5 (4)	O3—S1—C10—C11	60.9 (2)
N2—C2—C3—N1	0.3 (3)	O1—S1—C10—C11	−59.6 (2)
C7—C2—C3—N1	−177.5 (2)	O2—S1—C10—C11	−178.54 (17)
C1—N1—C3—C4	−178.4 (3)	C9—C10—C11—C12	−179.5 (2)
C1—N1—C3—C2	0.4 (3)	S1—C10—C11—C12	1.1 (3)
C2—C3—C4—C5	−1.2 (4)	C9—C10—C11—C11i	1.1 (4)
N1—C3—C4—C5	177.5 (3)	S1—C10—C11—C11i	−178.4 (2)
C3—C4—C5—C6	−0.2 (4)	C10—C11—C12—C13	−179.7 (2)
C4—C5—C6—C7	1.4 (5)	C11i—C11—C12—C13	−0.2 (4)
C5—C6—C7—C2	−1.2 (4)	C11—C12—C13—C9i	0.4 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2ii	0.86	1.86	2.704 (3)	165
N2—H2···O1	0.86	1.88	2.684 (3)	155
C8—H8E···O3iii	0.96	2.32	3.230 (4)	158
C4—H4···Cg1iv	0.93	2.61	3.468 (3)	154
C4—H4···Cg2v	0.93	2.61	3.468 (3)	154

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C9–C11/C11i/C12i/C13i and C11–C13/C9i/C10i/C11i rings, respectively [symmetry code: (i) −x, −y + 1, −z + 1].

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2ii	0.86	1.86	2.704 (3)	165
N2—H2⋯O1	0.86	1.88	2.684 (3)	155
C8—H8E⋯O3iii	0.96	2.32	3.230 (4)	158
C4—H4⋯Cg1iv	0.93	2.61	3.468 (3)	154
C4—H4⋯Cg2v	0.93	2.61	3.468 (3)	154

Symmetry codes: (ii) ; (iii) ; (iv) ; (v) .