organic compounds
Bis(2-methyl-1H-benzimidazol-3-ium) naphthalene-1,5-disulfonate
aTianmu College of ZheJiang A & F University, Lin'An 311300, People's Republic of China, and bFaculty of Science, ZheJiang A & F University, Lin'An 311300, People's Republic of China
*Correspondence e-mail: shouwenjin@yahoo.cn
The 8H9N2+·C10H6O6S22−, contains a 2-methylbenzimidazolium 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 interactions are observed. The methyl H atoms were refined as disordered over two sets of sites with equal occupancy.
of the title compound, 2CRelated 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
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Refinement
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Data collection: SMART (Bruker, 2002); cell 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).
Supporting information
https://doi.org/10.1107/S1600536812039396/lh5531sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812039396/lh5531Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536812039396/lh5531Isup3.cml
2-Methyl-1H-benzimidazole (24.0 mg, 0.20 mmol) was dissolved in 10 ml of methanol, and naphthalene-1,5-disulfonic acid tetrahydrate (36 mg, 0.1 mmol) was added. The solution was stirred for 1 h, and then filtered into a test tube. The solution was left standing at room temperature for about one week whereupon colorless block crystals were obtained.
All H atoms were positioned geometrically with C—H = 0.93–0.96 Å, N—H = 0.86 Å and constrained to ride on their parent atoms with Uiso(H) = 1.2Ueq(C,N). The methyl H atoms were refined as disordered over six sites with equal occupancy.
Sulfonic acids are important compounds, which have been widely used in various fields as coordination chemistry (Wang et al., 2005), pharmaceutical chemistry (Elder et al., 2010), and supramolecular chemistry (Voogt & Blanch, 2005). Recently the main focus for
has been in crystal engineering via hydrogen bonded assembly of sulfonic acid and organic base (Zhang et al., 2005). As an extension of our study concentrating on hydrogen bonded assemblies of organic acids and organic bases (Jin et al., 2012) herein we report the of the title compound (I).The molecular structure of (I) is shown in Fig. 1. The anion lies across an inversion center. In the crystal, N—H···O hydrogen bonds link the components into chains along [001] (Fig. 2). In addition, weak C—H···O hydrogen bonds and weak C—H···π interactions are observed.
For general background to organic [sulfonic?] acids, see: Jin et al. (2012); Elder et al. (2010); Voogt & Blanch (2005); Wang et al. (2005); Zhang et al. (2005).
Data collection: SMART (Bruker, 2002); cell
SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); 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).Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at the 30% probability level. Only the symmetry unique cation is shown and in the anion unlabeled atoms are related by the symmetry operator (-x, -y + 1, -z + 1). | |
Fig. 2. Part of the crystal structure with hydrogen bonds shown as dashed lines. H atoms not involved in the hydrogen bonds have been omitted for clarity. |
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) |
2C8H9N2+·C10H6O6S22− | γ = 106.497 (2)° |
Mr = 552.61 | V = 624.75 (10) Å3 |
Triclinic, P1 | Z = 1 |
a = 8.0360 (7) Å | Mo Kα radiation |
b = 9.3969 (8) Å | µ = 0.26 mm−1 |
c = 9.5101 (9) Å | T = 298 K |
α = 105.789 (1)° | 0.45 × 0.41 × 0.19 mm |
β = 103.303 (1)° |
Bruker SMART CCD diffractometer | 2169 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | 1694 reflections with I > 2σ(I) |
Tmin = 0.888, Tmax = 0.951 | Rint = 0.030 |
3137 measured reflections |
R[F2 > 2σ(F2)] = 0.043 | 0 restraints |
wR(F2) = 0.119 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.28 e Å−3 |
2169 reflections | Δρmin = −0.37 e Å−3 |
173 parameters |
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) |
Symmetry code: (i) −x, −y+1, −z+1. |
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) x, y, z−1; (iii) −x+1, −y+1, −z+1; (iv) −x, −y, −z; (v) x, y−1, z−1. |
Experimental details
Crystal data | |
Chemical formula | 2C8H9N2+·C10H6O6S22− |
Mr | 552.61 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 298 |
a, b, c (Å) | 8.0360 (7), 9.3969 (8), 9.5101 (9) |
α, β, γ (°) | 105.789 (1), 103.303 (1), 106.497 (2) |
V (Å3) | 624.75 (10) |
Z | 1 |
Radiation type | Mo Kα |
µ (mm−1) | 0.26 |
Crystal size (mm) | 0.45 × 0.41 × 0.19 |
Data collection | |
Diffractometer | Bruker SMART CCD |
Absorption correction | Multi-scan (SADABS; Bruker, 2002) |
Tmin, Tmax | 0.888, 0.951 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3137, 2169, 1694 |
Rint | 0.030 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.043, 0.119, 1.05 |
No. of reflections | 2169 |
No. of parameters | 173 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.28, −0.37 |
Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009), SHELXTL (Sheldrick, 2008).
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···O2i | 0.86 | 1.86 | 2.704 (3) | 165 |
N2—H2···O1 | 0.86 | 1.88 | 2.684 (3) | 155 |
C8—H8E···O3ii | 0.96 | 2.32 | 3.230 (4) | 158 |
C4—H4···Cg1iii | 0.93 | 2.61 | 3.468 (3) | 154 |
C4—H4···Cg2iv | 0.93 | 2.61 | 3.468 (3) | 154 |
Symmetry codes: (i) x, y, z−1; (ii) −x+1, −y+1, −z+1; (iii) −x, −y, −z; (iv) x, y−1, z−1. |
Acknowledgements
The authors gratefully acknowledge financial support from the Education Office Foundation of Zhejiang Province (project No. Y201017321) and the Innovation Project of Zhejiang A & F University.
References
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Sulfonic acids are important compounds, which have been widely used in various fields as coordination chemistry (Wang et al., 2005), pharmaceutical chemistry (Elder et al., 2010), and supramolecular chemistry (Voogt & Blanch, 2005). Recently the main focus for sulfonic acids has been in crystal engineering via hydrogen bonded assembly of sulfonic acid and organic base (Zhang et al., 2005). As an extension of our study concentrating on hydrogen bonded assemblies of organic acids and organic bases (Jin et al., 2012) herein we report the crystal structure of the title compound (I).
The molecular structure of (I) is shown in Fig. 1. The anion lies across an inversion center. In the crystal, N—H···O hydrogen bonds link the components into chains along [001] (Fig. 2). In addition, weak C—H···O hydrogen bonds and weak C—H···π interactions are observed.