Acta Cryst. (2008). E64, o674 [ doi:10.1107/S1600536808005916 ]
The title compound, 2C7H7N2+·C10H6O6S22-·3H2O, consists of two crystallographically independent benzimidazolium cations, two independent naphthalene-1,5-disulfonate dianions (both generated by inversion) and three water molecules. These components construct an infinite three-dimensional framework in the crystal structure via O-H
O and N-HO hydrogen bonds.
A 5-ml ethanol solution of benzimidazole (1.00 mmol, 0.118 g) was added to an aqueous solution (25 ml) of naphthalene-1,5-disulfonic acid (0.50 mmol, 0.15 g). The mixture was stirred for 10 minutes at 373 K. The solution was filtered, and the filtrate was allowed to stand at room temperature. After several days, colourless blocks of (I) were recovered.
The H atoms bonded to N and O were located in a difference map and refined with distance restraints [N—H = 0.90 (1) Å, water O—H = 0.85 (1)Å and H···H = 1.34 (1) Å]; their Uiso values were freely refined.
The C-bound H atoms were positioned geometrically (C—H = 0.93 Å) and refined as riding with Uiso(H) = 1.2Ueq(C).
Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON (Spek, 2003).
![[Figure 1]](./hb2700fig1thm.gif)
| Fig. 1. The molecular structure of (I). Displacement ellipsoids for non-H atoms are drawn at the 30% probability level. Hydrogen bonds are shown as dashed lines. Unlabeled atoms in the C8 anion are related to labeled atoms by (1 - x, 1 - y, 1 - z). Unlabeled atoms in the C20 anion are related to labeled atoms by (1 - x, 1 - y, -z). |
![[Figure 2]](./hb2700fig2thm.gif)
| Fig. 2. The crystal packing of (I). Hydrogen bonds are shown as dashed lines. For clarity, H atoms not involved in hydrogen bonds are omitted. |
| 2C7H7N2+·C10H6O6S22–·3H2O | Z = 2 |
| Mr = 578.61 | F000 = 604 |
| Triclinic, P1 | Dx = 1.437 Mg m−3 |
| Hall symbol: -P 1 | Mo Kα radiation λ = 0.71073 Å |
| a = 8.372 (4) Å | Cell parameters from 3010 reflections |
| b = 9.889 (5) Å | θ = 2.5–28.2º |
| c = 17.044 (8) Å | µ = 0.26 mm−1 |
| α = 80.914 (8)º | T = 296 (2) K |
| β = 87.557 (9)º | Block, colourless |
| γ = 73.641 (8)º | 0.15 × 0.12 × 0.04 mm |
| V = 1337.0 (11) Å3 |
| Bruker SMART APEX CCD diffractometer | 4670 independent reflections |
| Radiation source: fine-focus sealed tube | 3494 reflections with I > 2σ(I) |
| Monochromator: graphite | Rint = 0.020 |
| T = 296(2) K | θmax = 25.0º |
| ω scans | θmin = 2.2º |
| Absorption correction: multi-scan (SADABS; Bruker, 2001) | h = −9→6 |
| Tmin = 0.962, Tmax = 0.990 | k = −11→10 |
| 6891 measured reflections | l = −20→20 |
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: difmap and geom |
| R[F2 > 2σ(F2)] = 0.043 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.110 | w = 1/[σ2(Fo2) + (0.0559P)2 + 0.0198P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.06 | (Δ/σ)max < 0.001 |
| 4670 reflections | Δρmax = 0.30 e Å−3 |
| 392 parameters | Δρmin = −0.33 e Å−3 |
| 37 restraints | Extinction correction: none |
| Primary atom site location: structure-invariant direct methods |
| 2C7H7N2+·C10H6O6S22–·3H2O | γ = 73.641 (8)º |
| Mr = 578.61 | V = 1337.0 (11) Å3 |
| Triclinic, P1 | Z = 2 |
| a = 8.372 (4) Å | Mo Kα |
| b = 9.889 (5) Å | µ = 0.26 mm−1 |
| c = 17.044 (8) Å | T = 296 (2) K |
| α = 80.914 (8)º | 0.15 × 0.12 × 0.04 mm |
| β = 87.557 (9)º |
| Bruker SMART APEX CCD diffractometer | 4670 independent reflections |
| Absorption correction: multi-scan (SADABS; Bruker, 2001) | 3494 reflections with I > 2σ(I) |
| Tmin = 0.962, Tmax = 0.990 | Rint = 0.020 |
| 6891 measured reflections |
| R[F2 > 2σ(F2)] = 0.043 | 37 restraints |
| wR(F2) = 0.110 | H atoms treated by a mixture of independent and constrained refinement |
| S = 1.06 | Δρmax = 0.30 e Å−3 |
| 4670 reflections | Δρmin = −0.33 e Å−3 |
| 392 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 | ||
| S1 | 0.75176 (8) | 0.65881 (6) | 0.37087 (4) | 0.04129 (19) | |
| S2 | 0.39100 (7) | 0.25493 (6) | 0.14588 (3) | 0.03710 (17) | |
| N1 | 0.8368 (3) | 0.0653 (2) | 1.09595 (14) | 0.0502 (6) | |
| H1A | 0.794 (4) | −0.007 (2) | 1.1155 (19) | 0.098 (12)* | |
| N2 | 0.9885 (3) | 0.2131 (2) | 1.08427 (15) | 0.0505 (6) | |
| H2A | 1.065 (3) | 0.253 (3) | 1.0965 (18) | 0.082 (11)* | |
| N3 | 0.0749 (3) | 0.7339 (2) | 0.48285 (14) | 0.0460 (5) | |
| H3A | 0.032 (3) | 0.670 (2) | 0.4660 (15) | 0.063 (9)* | |
| N4 | 0.1689 (3) | 0.8418 (2) | 0.56460 (12) | 0.0432 (5) | |
| H4A | 0.192 (3) | 0.865 (3) | 0.6108 (9) | 0.056 (8)* | |
| O1 | 0.7659 (2) | 0.65613 (18) | 0.28505 (10) | 0.0554 (5) | |
| O2 | 0.6945 (2) | 0.80262 (17) | 0.39064 (11) | 0.0571 (5) | |
| O3 | 0.9056 (2) | 0.57458 (17) | 0.41288 (10) | 0.0473 (4) | |
| O4 | 0.21223 (19) | 0.33257 (17) | 0.14166 (10) | 0.0457 (4) | |
| O5 | 0.4281 (2) | 0.13448 (16) | 0.10230 (10) | 0.0490 (5) | |
| O6 | 0.4518 (2) | 0.21705 (18) | 0.22760 (10) | 0.0545 (5) | |
| O7 | 0.6702 (3) | 0.8721 (2) | 0.15255 (12) | 0.0636 (6) | |
| H7A | 0.695 (3) | 0.822 (3) | 0.1982 (9) | 0.072 (5)* | |
| H7B | 0.575 (2) | 0.928 (3) | 0.1601 (16) | 0.096 (14)* | |
| O8 | 0.7493 (3) | 0.0547 (2) | 0.30528 (12) | 0.0573 (5) | |
| H8A | 0.733 (3) | −0.0213 (17) | 0.3299 (15) | 0.067 (5)* | |
| H8B | 0.657 (2) | 0.102 (3) | 0.283 (2) | 0.130 (17)* | |
| O9 | 0.0253 (4) | 0.6345 (3) | 0.73328 (16) | 0.0971 (8) | |
| H9A | −0.066 (2) | 0.618 (3) | 0.719 (2) | 0.081 (5)* | |
| H9B | 0.089 (3) | 0.5484 (16) | 0.743 (2) | 0.101 (6)* | |
| C1 | 0.9359 (3) | 0.1177 (3) | 1.13375 (17) | 0.0546 (7) | |
| H1 | 0.9641 | 0.0912 | 1.1873 | 0.065* | |
| C2 | 0.8228 (3) | 0.1305 (2) | 1.01695 (16) | 0.0421 (6) | |
| C3 | 0.7326 (3) | 0.1173 (3) | 0.95341 (18) | 0.0548 (7) | |
| H3 | 0.6675 | 0.0541 | 0.9585 | 0.066* | |
| C4 | 0.7446 (4) | 0.2034 (3) | 0.88195 (18) | 0.0619 (8) | |
| H4 | 0.6861 | 0.1975 | 0.8380 | 0.074* | |
| C5 | 0.8424 (4) | 0.2990 (3) | 0.87418 (18) | 0.0626 (8) | |
| H5 | 0.8468 | 0.3547 | 0.8252 | 0.075* | |
| C6 | 0.9320 (3) | 0.3128 (3) | 0.93678 (17) | 0.0532 (7) | |
| H6 | 0.9967 | 0.3763 | 0.9314 | 0.064* | |
| C7 | 0.9205 (3) | 0.2262 (2) | 1.00908 (16) | 0.0428 (6) | |
| C8 | 0.4007 (3) | 0.4475 (3) | 0.37232 (15) | 0.0514 (7) | |
| H8 | 0.3477 | 0.4186 | 0.3338 | 0.062* | |
| C9 | 0.5171 (3) | 0.5243 (3) | 0.34934 (15) | 0.0455 (6) | |
| H9 | 0.5410 | 0.5452 | 0.2957 | 0.055* | |
| C10 | 0.5963 (3) | 0.5689 (2) | 0.40503 (13) | 0.0360 (5) | |
| C11 | 0.5595 (3) | 0.5398 (2) | 0.48859 (13) | 0.0348 (5) | |
| C12 | 0.6357 (3) | 0.5851 (3) | 0.54888 (14) | 0.0442 (6) | |
| H12 | 0.7114 | 0.6378 | 0.5346 | 0.053* | |
| C13 | 0.0892 (3) | 0.7450 (3) | 0.55844 (16) | 0.0478 (7) | |
| H13 | 0.0493 | 0.6927 | 0.6011 | 0.057* | |
| C14 | 0.1487 (3) | 0.8290 (2) | 0.43592 (14) | 0.0392 (6) | |
| C15 | 0.1657 (3) | 0.8615 (3) | 0.35337 (16) | 0.0541 (7) | |
| H15 | 0.1264 | 0.8154 | 0.3181 | 0.065* | |
| C16 | 0.2444 (4) | 0.9660 (3) | 0.32755 (17) | 0.0620 (8) | |
| H16 | 0.2584 | 0.9907 | 0.2733 | 0.074* | |
| C17 | 0.3036 (3) | 1.0360 (3) | 0.38033 (18) | 0.0578 (8) | |
| H17 | 0.3552 | 1.1060 | 0.3601 | 0.069* | |
| C18 | 0.2877 (3) | 1.0043 (3) | 0.46113 (16) | 0.0477 (6) | |
| H18 | 0.3274 | 1.0507 | 0.4960 | 0.057* | |
| C19 | 0.2086 (3) | 0.8982 (2) | 0.48839 (14) | 0.0369 (6) | |
| C20 | 0.6767 (3) | 0.5287 (2) | 0.11047 (14) | 0.0394 (6) | |
| H20 | 0.7486 | 0.5548 | 0.1414 | 0.047* | |
| C21 | 0.6018 (3) | 0.4208 (2) | 0.14309 (13) | 0.0357 (5) | |
| H21 | 0.6249 | 0.3764 | 0.1953 | 0.043* | |
| C22 | 0.4946 (3) | 0.3809 (2) | 0.09785 (13) | 0.0308 (5) | |
| C23 | 0.4614 (3) | 0.4453 (2) | 0.01605 (12) | 0.0288 (5) | |
| C24 | 0.3560 (3) | 0.4050 (2) | −0.03388 (13) | 0.0353 (5) | |
| H24 | 0.3084 | 0.3323 | −0.0139 | 0.042* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| S1 | 0.0484 (4) | 0.0338 (3) | 0.0428 (4) | −0.0151 (3) | −0.0003 (3) | −0.0022 (3) |
| S2 | 0.0385 (4) | 0.0360 (3) | 0.0376 (3) | −0.0162 (3) | 0.0002 (3) | 0.0027 (3) |
| N1 | 0.0443 (13) | 0.0410 (13) | 0.0639 (16) | −0.0139 (11) | 0.0030 (11) | −0.0011 (11) |
| N2 | 0.0383 (13) | 0.0498 (14) | 0.0660 (16) | −0.0161 (11) | −0.0060 (11) | −0.0082 (12) |
| N3 | 0.0469 (13) | 0.0372 (12) | 0.0571 (15) | −0.0157 (10) | −0.0011 (11) | −0.0087 (11) |
| N4 | 0.0488 (13) | 0.0396 (12) | 0.0397 (13) | −0.0117 (10) | −0.0042 (10) | −0.0018 (10) |
| O1 | 0.0689 (13) | 0.0589 (12) | 0.0399 (10) | −0.0246 (10) | 0.0042 (9) | −0.0003 (9) |
| O2 | 0.0714 (13) | 0.0312 (9) | 0.0693 (13) | −0.0159 (9) | 0.0042 (10) | −0.0072 (9) |
| O3 | 0.0444 (10) | 0.0422 (10) | 0.0567 (11) | −0.0170 (8) | −0.0044 (8) | −0.0020 (8) |
| O4 | 0.0346 (10) | 0.0478 (10) | 0.0541 (11) | −0.0140 (8) | 0.0058 (8) | −0.0033 (8) |
| O5 | 0.0555 (11) | 0.0317 (9) | 0.0634 (12) | −0.0180 (8) | 0.0009 (9) | −0.0069 (8) |
| O6 | 0.0642 (12) | 0.0609 (12) | 0.0395 (10) | −0.0306 (10) | −0.0067 (9) | 0.0153 (8) |
| O7 | 0.0655 (15) | 0.0497 (13) | 0.0740 (15) | −0.0202 (12) | −0.0078 (11) | 0.0045 (10) |
| O8 | 0.0676 (14) | 0.0493 (12) | 0.0582 (13) | −0.0246 (11) | −0.0130 (11) | 0.0009 (10) |
| O9 | 0.109 (2) | 0.0876 (17) | 0.0720 (16) | 0.0001 (16) | 0.0210 (16) | −0.0007 (14) |
| C1 | 0.0467 (17) | 0.0544 (17) | 0.0579 (18) | −0.0094 (14) | −0.0031 (14) | −0.0022 (14) |
| C2 | 0.0341 (14) | 0.0358 (14) | 0.0562 (17) | −0.0083 (11) | 0.0035 (12) | −0.0099 (12) |
| C3 | 0.0445 (16) | 0.0523 (17) | 0.074 (2) | −0.0178 (13) | 0.0072 (14) | −0.0234 (15) |
| C4 | 0.0578 (19) | 0.069 (2) | 0.061 (2) | −0.0145 (16) | −0.0041 (15) | −0.0214 (16) |
| C5 | 0.065 (2) | 0.0580 (19) | 0.0579 (19) | −0.0107 (16) | 0.0059 (16) | −0.0032 (15) |
| C6 | 0.0507 (17) | 0.0434 (15) | 0.0679 (19) | −0.0184 (13) | 0.0076 (15) | −0.0078 (14) |
| C7 | 0.0331 (14) | 0.0369 (14) | 0.0585 (17) | −0.0084 (11) | 0.0032 (12) | −0.0112 (12) |
| C8 | 0.0587 (17) | 0.0617 (17) | 0.0434 (16) | −0.0275 (15) | −0.0076 (13) | −0.0147 (13) |
| C9 | 0.0541 (16) | 0.0511 (15) | 0.0341 (13) | −0.0175 (13) | −0.0024 (12) | −0.0087 (12) |
| C10 | 0.0384 (14) | 0.0325 (12) | 0.0363 (13) | −0.0083 (10) | −0.0013 (11) | −0.0054 (10) |
| C11 | 0.0360 (13) | 0.0296 (12) | 0.0400 (13) | −0.0095 (10) | −0.0027 (10) | −0.0074 (10) |
| C12 | 0.0474 (15) | 0.0487 (15) | 0.0441 (15) | −0.0229 (13) | −0.0004 (12) | −0.0118 (12) |
| C13 | 0.0498 (16) | 0.0364 (14) | 0.0532 (17) | −0.0104 (12) | 0.0041 (13) | 0.0014 (12) |
| C14 | 0.0350 (13) | 0.0358 (13) | 0.0450 (15) | −0.0080 (11) | 0.0009 (11) | −0.0047 (11) |
| C15 | 0.0566 (18) | 0.0572 (17) | 0.0471 (16) | −0.0108 (14) | −0.0004 (13) | −0.0130 (13) |
| C16 | 0.067 (2) | 0.068 (2) | 0.0452 (17) | −0.0154 (17) | 0.0105 (15) | −0.0002 (15) |
| C17 | 0.0546 (18) | 0.0537 (17) | 0.0628 (19) | −0.0193 (15) | 0.0120 (15) | 0.0027 (15) |
| C18 | 0.0410 (15) | 0.0443 (15) | 0.0606 (18) | −0.0165 (12) | 0.0006 (13) | −0.0074 (13) |
| C19 | 0.0326 (13) | 0.0336 (13) | 0.0413 (14) | −0.0058 (11) | −0.0028 (11) | −0.0020 (11) |
| C20 | 0.0410 (14) | 0.0432 (14) | 0.0399 (14) | −0.0193 (12) | −0.0071 (11) | −0.0076 (11) |
| C21 | 0.0407 (14) | 0.0372 (13) | 0.0294 (12) | −0.0121 (11) | −0.0022 (10) | −0.0030 (10) |
| C22 | 0.0314 (12) | 0.0278 (12) | 0.0329 (12) | −0.0079 (10) | 0.0016 (10) | −0.0045 (9) |
| C23 | 0.0276 (12) | 0.0273 (12) | 0.0319 (12) | −0.0078 (9) | 0.0037 (10) | −0.0062 (10) |
| C24 | 0.0381 (13) | 0.0343 (13) | 0.0379 (13) | −0.0185 (11) | −0.0001 (10) | −0.0030 (10) |
| S1—O2 | 1.4558 (18) | C5—H5 | 0.9300 |
| S1—O1 | 1.4663 (19) | C6—C7 | 1.402 (4) |
| S1—O3 | 1.4665 (18) | C6—H6 | 0.9300 |
| S1—C10 | 1.802 (2) | C8—C12i | 1.373 (3) |
| S2—O5 | 1.4555 (18) | C8—C9 | 1.404 (3) |
| S2—O6 | 1.4586 (18) | C8—H8 | 0.9300 |
| S2—O4 | 1.4761 (18) | C9—C10 | 1.373 (3) |
| S2—C22 | 1.789 (2) | C9—H9 | 0.9300 |
| N1—C1 | 1.329 (3) | C10—C11 | 1.445 (3) |
| N1—C2 | 1.393 (3) | C11—C12 | 1.423 (3) |
| N1—H1A | 0.898 (10) | C11—C11i | 1.442 (4) |
| N2—C1 | 1.322 (3) | C12—C8i | 1.373 (3) |
| N2—C7 | 1.397 (3) | C12—H12 | 0.9300 |
| N2—H2A | 0.887 (18) | C13—H13 | 0.9300 |
| N3—C13 | 1.323 (3) | C14—C19 | 1.394 (3) |
| N3—C14 | 1.398 (3) | C14—C15 | 1.403 (3) |
| N3—H3A | 0.895 (10) | C15—C16 | 1.382 (4) |
| N4—C13 | 1.330 (3) | C15—H15 | 0.9300 |
| N4—C19 | 1.396 (3) | C16—C17 | 1.401 (4) |
| N4—H4A | 0.899 (10) | C16—H16 | 0.9300 |
| O7—H7A | 0.853 (10) | C17—C18 | 1.373 (4) |
| O7—H7B | 0.852 (10) | C17—H17 | 0.9300 |
| O8—H8A | 0.844 (10) | C18—C19 | 1.402 (3) |
| O8—H8B | 0.847 (10) | C18—H18 | 0.9300 |
| O9—H9A | 0.871 (10) | C20—C24ii | 1.367 (3) |
| O9—H9B | 0.863 (10) | C20—C21 | 1.414 (3) |
| C1—H1 | 0.9300 | C20—H20 | 0.9300 |
| C2—C3 | 1.389 (4) | C21—C22 | 1.382 (3) |
| C2—C7 | 1.403 (3) | C21—H21 | 0.9300 |
| C3—C4 | 1.389 (4) | C22—C23 | 1.442 (3) |
| C3—H3 | 0.9300 | C23—C24 | 1.425 (3) |
| C4—C5 | 1.403 (4) | C23—C23ii | 1.436 (4) |
| C4—H4 | 0.9300 | C24—C20ii | 1.367 (3) |
| C5—C6 | 1.375 (4) | C24—H24 | 0.9300 |
| O2—S1—O1 | 113.02 (11) | C9—C8—H8 | 119.7 |
| O2—S1—O3 | 112.36 (11) | C10—C9—C8 | 120.8 (2) |
| O1—S1—O3 | 111.76 (11) | C10—C9—H9 | 119.6 |
| O2—S1—C10 | 107.58 (11) | C8—C9—H9 | 119.6 |
| O1—S1—C10 | 105.71 (11) | C9—C10—C11 | 120.7 (2) |
| O3—S1—C10 | 105.83 (10) | C9—C10—S1 | 117.92 (18) |
| O5—S2—O6 | 113.58 (11) | C11—C10—S1 | 121.33 (17) |
| O5—S2—O4 | 111.49 (10) | C12—C11—C11i | 118.8 (3) |
| O6—S2—O4 | 111.78 (11) | C12—C11—C10 | 123.3 (2) |
| O5—S2—C22 | 108.32 (10) | C11i—C11—C10 | 117.9 (3) |
| O6—S2—C22 | 106.06 (10) | C8i—C12—C11 | 121.2 (2) |
| O4—S2—C22 | 105.02 (10) | C8i—C12—H12 | 119.4 |
| C1—N1—C2 | 108.7 (2) | C11—C12—H12 | 119.4 |
| C1—N1—H1A | 127 (2) | N3—C13—N4 | 110.2 (2) |
| C2—N1—H1A | 124 (2) | N3—C13—H13 | 124.9 |
| C1—N2—C7 | 109.1 (2) | N4—C13—H13 | 124.9 |
| C1—N2—H2A | 124 (2) | C19—C14—N3 | 106.2 (2) |
| C7—N2—H2A | 126 (2) | C19—C14—C15 | 121.6 (2) |
| C13—N3—C14 | 108.8 (2) | N3—C14—C15 | 132.2 (2) |
| C13—N3—H3A | 124.4 (18) | C16—C15—C14 | 116.0 (3) |
| C14—N3—H3A | 126.6 (18) | C16—C15—H15 | 122.0 |
| C13—N4—C19 | 108.6 (2) | C14—C15—H15 | 122.0 |
| C13—N4—H4A | 124.5 (17) | C15—C16—C17 | 122.3 (3) |
| C19—N4—H4A | 126.9 (17) | C15—C16—H16 | 118.9 |
| H7A—O7—H7B | 103.0 (15) | C17—C16—H16 | 118.9 |
| H8A—O8—H8B | 105.6 (15) | C18—C17—C16 | 121.9 (3) |
| H9A—O9—H9B | 100.1 (14) | C18—C17—H17 | 119.1 |
| N2—C1—N1 | 110.2 (3) | C16—C17—H17 | 119.1 |
| N2—C1—H1 | 124.9 | C17—C18—C19 | 116.6 (3) |
| N1—C1—H1 | 124.9 | C17—C18—H18 | 121.7 |
| C3—C2—N1 | 132.0 (2) | C19—C18—H18 | 121.7 |
| C3—C2—C7 | 121.6 (2) | C14—C19—N4 | 106.3 (2) |
| N1—C2—C7 | 106.4 (2) | C14—C19—C18 | 121.6 (2) |
| C4—C3—C2 | 116.5 (3) | N4—C19—C18 | 132.1 (2) |
| C4—C3—H3 | 121.8 | C24ii—C20—C21 | 120.5 (2) |
| C2—C3—H3 | 121.8 | C24ii—C20—H20 | 119.7 |
| C3—C4—C5 | 121.9 (3) | C21—C20—H20 | 119.7 |
| C3—C4—H4 | 119.1 | C22—C21—C20 | 120.4 (2) |
| C5—C4—H4 | 119.1 | C22—C21—H21 | 119.8 |
| C6—C5—C4 | 122.0 (3) | C20—C21—H21 | 119.8 |
| C6—C5—H5 | 119.0 | C21—C22—C23 | 120.6 (2) |
| C4—C5—H5 | 119.0 | C21—C22—S2 | 117.66 (17) |
| C5—C6—C7 | 116.4 (3) | C23—C22—S2 | 121.65 (16) |
| C5—C6—H6 | 121.8 | C24—C23—C23ii | 118.9 (2) |
| C7—C6—H6 | 121.8 | C24—C23—C22 | 122.86 (19) |
| N2—C7—C6 | 132.7 (2) | C23ii—C23—C22 | 118.2 (2) |
| N2—C7—C2 | 105.7 (2) | C20ii—C24—C23 | 121.3 (2) |
| C6—C7—C2 | 121.6 (3) | C20ii—C24—H24 | 119.3 |
| C12i—C8—C9 | 120.6 (2) | C23—C24—H24 | 119.3 |
| C12i—C8—H8 | 119.7 |
| Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+1, −z. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H1A···O7iii | 0.898 (10) | 1.820 (12) | 2.708 (3) | 170 (3) |
| N2—H2A···O4iv | 0.887 (18) | 1.885 (19) | 2.762 (3) | 170 (3) |
| N3—H3A···O3v | 0.895 (10) | 1.937 (12) | 2.812 (3) | 166 (2) |
| N4—H4A···O8i | 0.899 (10) | 1.883 (11) | 2.771 (3) | 169 (2) |
| O7—H7B···O5vi | 0.852 (10) | 2.169 (19) | 2.839 (3) | 135 (2) |
| O8—H8A···O2vii | 0.844 (10) | 1.982 (10) | 2.826 (3) | 178 (3) |
| O7—H7A···O1 | 0.853 (10) | 1.999 (12) | 2.823 (3) | 162 (3) |
| O8—H8B···O6 | 0.847 (10) | 1.963 (10) | 2.809 (3) | 176 (3) |
| O9—H9B···O1i | 0.863 (10) | 2.157 (18) | 2.970 (3) | 157 (3) |
| Symmetry codes: (iii) x, y−1, z+1; (iv) x+1, y, z+1; (v) x−1, y, z; (i) −x+1, −y+1, −z+1; (vi) x, y+1, z; (vii) x, y−1, z. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H1A···O7i | 0.898 (10) | 1.820 (12) | 2.708 (3) | 170 (3) |
| N2—H2A···O4ii | 0.887 (18) | 1.885 (19) | 2.762 (3) | 170 (3) |
| N3—H3A···O3iii | 0.895 (10) | 1.937 (12) | 2.812 (3) | 166 (2) |
| N4—H4A···O8iv | 0.899 (10) | 1.883 (11) | 2.771 (3) | 169 (2) |
| O7—H7B···O5v | 0.852 (10) | 2.169 (19) | 2.839 (3) | 135 (2) |
| O8—H8A···O2vi | 0.844 (10) | 1.982 (10) | 2.826 (3) | 178 (3) |
| O7—H7A···O1 | 0.853 (10) | 1.999 (12) | 2.823 (3) | 162 (3) |
| O8—H8B···O6 | 0.847 (10) | 1.963 (10) | 2.809 (3) | 176 (3) |
| O9—H9B···O1iv | 0.863 (10) | 2.157 (18) | 2.970 (3) | 157 (3) |
| Symmetry codes: (i) x, y−1, z+1; (ii) x+1, y, z+1; (iii) x−1, y, z; (iv) −x+1, −y+1, −z+1; (v) x, y+1, z; (vi) x, y−1, z. |
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Wang, Z.-L. & Wei, L.-H. (2007). Acta Cryst. E63, o1448–o1449.
This work continues our previous synthetic and structural studies of supramolecular interactions in aromatic molecular salts and adducts (Wang & Wei, 2007). Herein we report the structure of the title salt, (I).
The title compound (I) contains two independent benzimidazolium cations, two naphthalene-1,5-disulfonate dianions and three water molecules (Fig. 1). Each of the dianions occupies a special position on an inversion centre. Therefore, the asymmetric unit of the crystal structure is composed of two half naphthalene-1,5-disulfonate dianions, two benzimidazolium cations and three water molecules.
These ions and molecules are finally organized into an infinite three-dimensional framework through N—H···O and O—H···O hydrogen bonds (Fig. 2 and Table 1).