Acta Cryst. (2008). E64, o734 [ doi:10.1107/S160053680800723X ]
The asymmetric unit of the title salt, C13H16N22+·C10H6O6S22-·2H2O, consists of one dication located on a general position, half each of two centrosymmetric dianions, and two uncoordinated water molecules in general positions. In the dication, the dihedral angle between the benzene rings is 74.67 (6)°. The cations and anions interact through N-H
O hydrogen bonds. The NH3+ functional groups are also involved in N-HO hydrogen bonds with the water molecules, forming an infinite three-dimensional framework in the crystal structure.
A 5 ml e thanol solution of 4,4'-methylene-bis(benzenamine) (0.5 mmol, 0.10 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 min. at 373 K. The solution was filtered, and the filtrate was allowed to stand at room temperature. After several days, colourless crystals suitable for X-ray diffraction were obtained.
H atoms for water molecules O1W and O2W were located in a difference map and refined with a geometry regularized through restrictions for distances: O—H = 0.85 (1) and H···H = 1.34 (1) Å. In order to reduce isotropic displacement parameters for water H atoms, SIMU restraints (similar Uij components; Sheldrick, 2008) were applied for water molecules. Other H atoms were placed in calculated positions with bond lengths fixed to N—H = 0.89, C—H = 0.93 (aromatic CH) and C—H = 0.97 Å (methylene CH2 group) and were refined as riding atoms, with Uiso(H) = 1.5 Ueq(carrier N) or Uiso(H) = 1.2 Ueq(carrier C).
Data collection: SMART (Bruker, 2003); cell refinement: SMART (Bruker, 2003); data reduction: SAINT-Plus (Bruker, 2003); 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]](./bh2163fig1thm.gif)
| Fig. 1. The structure of (I) including the asymmetric unit (labeled atoms) and anions completed through symmetry operators: unlabeled atoms in the C10 anion are related to labeled atoms by symmetry code -x + 1, -y, -z + 1; unlabeled atoms in the C16 anion are related to labeled atoms by symmetry code -x + 1, -y, -z. Displacement ellipsoids for non-H atoms are drawn at the 30% probability level. Hydrogen bonds are shown as dashed lines. |
![[Figure 2]](./bh2163fig2thm.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. |
| C13H16N22+·C10H6O6S22–·2H2O | Z = 2 |
| Mr = 522.58 | F000 = 548 |
| Triclinic, P1 | Dx = 1.460 Mg m−3 |
| Hall symbol: -P 1 | Mo Kα radiation λ = 0.71073 Å |
| a = 7.9652 (6) Å | Cell parameters from 3560 reflections |
| b = 10.9135 (8) Å | θ = 2.3–28.5º |
| c = 13.8158 (10) Å | µ = 0.28 mm−1 |
| α = 87.429 (1)º | T = 296 (2) K |
| β = 85.820 (1)º | Block, colourless |
| γ = 83.262 (1)º | 0.13 × 0.10 × 0.08 mm |
| V = 1188.72 (15) Å3 |
| Bruker SMART APEX CCD area-detector diffractometer | 4644 independent reflections |
| Radiation source: fine-focus sealed tube | 3999 reflections with I > 2σ(I) |
| Monochromator: graphite | Rint = 0.015 |
| T = 296(2) K | θmax = 26.0º |
| ω scans | θmin = 1.9º |
| Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | h = −9→9 |
| Tmin = 0.966, Tmax = 0.978 | k = −13→13 |
| 12513 measured reflections | l = −17→17 |
| 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)] = 0.039 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.117 | w = 1/[σ2(Fo2) + (0.0622P)2 + 0.4195P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.08 | (Δ/σ)max < 0.001 |
| 4644 reflections | Δρmax = 0.30 e Å−3 |
| 334 parameters | Δρmin = −0.30 e Å−3 |
| 30 restraints | Extinction correction: none |
| Primary atom site location: structure-invariant direct methods |
| C13H16N22+·C10H6O6S22–·2H2O | γ = 83.262 (1)º |
| Mr = 522.58 | V = 1188.72 (15) Å3 |
| Triclinic, P1 | Z = 2 |
| a = 7.9652 (6) Å | Mo Kα |
| b = 10.9135 (8) Å | µ = 0.28 mm−1 |
| c = 13.8158 (10) Å | T = 296 (2) K |
| α = 87.429 (1)º | 0.13 × 0.10 × 0.08 mm |
| β = 85.820 (1)º |
| Bruker SMART APEX CCD area-detector diffractometer | 4644 independent reflections |
| Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | 3999 reflections with I > 2σ(I) |
| Tmin = 0.966, Tmax = 0.978 | Rint = 0.015 |
| 12513 measured reflections |
| R[F2 > 2σ(F2)] = 0.039 | 30 restraints |
| wR(F2) = 0.117 | H atoms treated by a mixture of independent and constrained refinement |
| S = 1.08 | Δρmax = 0.30 e Å−3 |
| 4644 reflections | Δρmin = −0.30 e Å−3 |
| 334 parameters |
| x | y | z | Uiso*/Ueq | ||
| S1 | 0.40383 (6) | 0.31683 (4) | 0.49763 (3) | 0.04147 (14) | |
| S2 | 0.37003 (7) | 0.28607 (4) | 0.09053 (4) | 0.04796 (16) | |
| N1 | 0.4334 (2) | 0.52270 (16) | 0.28512 (13) | 0.0515 (4) | |
| H1A | 0.4107 | 0.4478 | 0.3063 | 0.077* | |
| H1B | 0.4850 | 0.5571 | 0.3302 | 0.077* | |
| H1C | 0.5006 | 0.5166 | 0.2308 | 0.077* | |
| N1A | −0.0574 (3) | 1.33594 (17) | 0.21344 (16) | 0.0635 (5) | |
| H1A1 | 0.0516 | 1.3376 | 0.1947 | 0.095* | |
| H1A2 | −0.0772 | 1.3627 | 0.2736 | 0.095* | |
| H1A3 | −0.1207 | 1.3845 | 0.1734 | 0.095* | |
| O1 | 0.4100 (2) | 0.32750 (13) | 0.60152 (11) | 0.0566 (4) | |
| O2 | 0.5575 (2) | 0.34399 (13) | 0.44339 (12) | 0.0595 (4) | |
| O3 | 0.2547 (2) | 0.38716 (13) | 0.46064 (14) | 0.0666 (5) | |
| O4 | 0.5241 (2) | 0.33961 (14) | 0.05942 (14) | 0.0723 (5) | |
| O5 | 0.3092 (2) | 0.31235 (14) | 0.18981 (12) | 0.0669 (5) | |
| O6 | 0.2382 (2) | 0.31961 (13) | 0.02363 (12) | 0.0615 (4) | |
| O1W | 0.2991 (2) | 0.49532 (17) | 0.87440 (13) | 0.0664 (4) | |
| H1WA | 0.358 (3) | 0.541 (2) | 0.9040 (17) | 0.079 (5)* | |
| H1WB | 0.273 (4) | 0.4416 (19) | 0.9181 (15) | 0.085 (5)* | |
| O2W | 0.0816 (3) | 0.5858 (2) | 0.59992 (18) | 0.0880 (6) | |
| H2WA | 0.171 (2) | 0.538 (2) | 0.610 (2) | 0.088 (5)* | |
| H2WB | 0.014 (3) | 0.542 (2) | 0.578 (3) | 0.111 (5)* | |
| C1 | −0.0257 (2) | 0.74496 (17) | 0.22988 (14) | 0.0439 (4) | |
| C2 | 0.0752 (3) | 0.68758 (19) | 0.15493 (14) | 0.0485 (5) | |
| H2 | 0.0409 | 0.6979 | 0.0919 | 0.058* | |
| C3 | 0.2255 (3) | 0.61548 (18) | 0.17187 (14) | 0.0457 (4) | |
| H3 | 0.2924 | 0.5783 | 0.1209 | 0.055* | |
| C4 | 0.2745 (2) | 0.59965 (16) | 0.26548 (14) | 0.0404 (4) | |
| C5 | 0.1767 (3) | 0.65344 (17) | 0.34204 (14) | 0.0450 (4) | |
| H5 | 0.2110 | 0.6411 | 0.4050 | 0.054* | |
| C6 | 0.0275 (3) | 0.72579 (18) | 0.32417 (14) | 0.0466 (4) | |
| H6 | −0.0388 | 0.7624 | 0.3756 | 0.056* | |
| C7 | −0.1870 (3) | 0.8271 (2) | 0.21082 (17) | 0.0532 (5) | |
| H7A | −0.2744 | 0.8101 | 0.2606 | 0.064* | |
| H7B | −0.2248 | 0.8081 | 0.1486 | 0.064* | |
| C8 | 0.3828 (2) | 0.15788 (15) | 0.48048 (12) | 0.0361 (4) | |
| C9 | 0.2418 (2) | 0.13005 (17) | 0.43965 (14) | 0.0434 (4) | |
| H9 | 0.1597 | 0.1931 | 0.4217 | 0.052* | |
| C10 | 0.2200 (3) | 0.00641 (18) | 0.42456 (15) | 0.0459 (4) | |
| H10 | 0.1227 | −0.0117 | 0.3974 | 0.055* | |
| C11 | 0.6604 (2) | 0.08693 (16) | 0.55070 (13) | 0.0410 (4) | |
| H11 | 0.6764 | 0.1680 | 0.5620 | 0.049* | |
| C12 | 0.5117 (2) | 0.06267 (15) | 0.50798 (11) | 0.0330 (4) | |
| C13 | 0.4159 (2) | 0.12309 (16) | 0.08655 (13) | 0.0387 (4) | |
| C14 | 0.4905 (2) | 0.06601 (15) | 0.00027 (13) | 0.0342 (4) | |
| C15 | 0.5455 (2) | 0.13320 (16) | −0.08410 (14) | 0.0424 (4) | |
| H15 | 0.5351 | 0.2190 | −0.0839 | 0.051* | |
| C16 | 0.6129 (3) | 0.07474 (18) | −0.16519 (15) | 0.0521 (5) | |
| H16 | 0.6467 | 0.1208 | −0.2199 | 0.062* | |
| C17 | 0.3680 (3) | 0.05438 (18) | 0.16698 (14) | 0.0503 (5) | |
| H17 | 0.3225 | 0.0935 | 0.2230 | 0.060* | |
| C1A | −0.1634 (2) | 0.96266 (19) | 0.21010 (14) | 0.0461 (4) | |
| C2A | −0.2043 (3) | 1.0326 (2) | 0.29072 (17) | 0.0642 (6) | |
| H2A | −0.2545 | 0.9966 | 0.3461 | 0.077* | |
| C3A | −0.1734 (3) | 1.1542 (2) | 0.29229 (18) | 0.0649 (6) | |
| H3A | −0.2018 | 1.1990 | 0.3480 | 0.078* | |
| C4A | −0.1006 (3) | 1.20806 (19) | 0.21109 (16) | 0.0508 (5) | |
| C5A | −0.0614 (4) | 1.1428 (2) | 0.12952 (18) | 0.0773 (8) | |
| H5A | −0.0133 | 1.1800 | 0.0740 | 0.093* | |
| C6A | −0.0929 (4) | 1.0208 (2) | 0.12897 (17) | 0.0735 (7) | |
| H6A | −0.0660 | 0.9770 | 0.0726 | 0.088* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| S1 | 0.0483 (3) | 0.0258 (2) | 0.0497 (3) | −0.00183 (18) | −0.0032 (2) | −0.00024 (18) |
| S2 | 0.0611 (3) | 0.0264 (2) | 0.0561 (3) | −0.0029 (2) | −0.0017 (2) | −0.00822 (19) |
| N1 | 0.0616 (11) | 0.0389 (9) | 0.0524 (10) | 0.0040 (8) | −0.0110 (8) | 0.0015 (7) |
| N1A | 0.0630 (12) | 0.0455 (10) | 0.0768 (13) | 0.0069 (9) | 0.0045 (10) | 0.0060 (9) |
| O1 | 0.0774 (10) | 0.0408 (8) | 0.0526 (9) | −0.0095 (7) | −0.0006 (7) | −0.0113 (6) |
| O2 | 0.0672 (10) | 0.0366 (7) | 0.0731 (10) | −0.0118 (7) | 0.0141 (8) | 0.0023 (7) |
| O3 | 0.0683 (10) | 0.0322 (7) | 0.0996 (13) | 0.0047 (7) | −0.0284 (9) | 0.0023 (7) |
| O4 | 0.0768 (11) | 0.0421 (8) | 0.1011 (14) | −0.0221 (8) | 0.0043 (10) | −0.0137 (8) |
| O5 | 0.0972 (13) | 0.0412 (8) | 0.0606 (10) | 0.0018 (8) | 0.0009 (9) | −0.0181 (7) |
| O6 | 0.0727 (10) | 0.0348 (7) | 0.0754 (11) | 0.0048 (7) | −0.0159 (8) | 0.0043 (7) |
| O1W | 0.0779 (11) | 0.0591 (10) | 0.0653 (10) | −0.0166 (8) | −0.0188 (9) | 0.0083 (8) |
| O2W | 0.0815 (14) | 0.0805 (14) | 0.1024 (16) | −0.0080 (11) | 0.0011 (12) | −0.0227 (12) |
| C1 | 0.0446 (10) | 0.0385 (10) | 0.0500 (11) | −0.0097 (8) | −0.0055 (8) | 0.0018 (8) |
| C2 | 0.0612 (12) | 0.0451 (11) | 0.0396 (10) | −0.0037 (9) | −0.0107 (9) | 0.0003 (8) |
| C3 | 0.0595 (12) | 0.0370 (10) | 0.0398 (10) | −0.0013 (8) | −0.0025 (9) | −0.0042 (8) |
| C4 | 0.0503 (11) | 0.0273 (8) | 0.0441 (10) | −0.0058 (7) | −0.0062 (8) | 0.0004 (7) |
| C5 | 0.0588 (12) | 0.0392 (10) | 0.0382 (10) | −0.0089 (9) | −0.0079 (8) | 0.0021 (8) |
| C6 | 0.0523 (11) | 0.0438 (10) | 0.0432 (10) | −0.0066 (9) | 0.0027 (8) | −0.0036 (8) |
| C7 | 0.0434 (11) | 0.0549 (12) | 0.0615 (13) | −0.0049 (9) | −0.0071 (9) | 0.0006 (10) |
| C8 | 0.0441 (10) | 0.0274 (8) | 0.0360 (9) | −0.0027 (7) | −0.0007 (7) | 0.0002 (7) |
| C9 | 0.0471 (10) | 0.0346 (9) | 0.0478 (10) | 0.0008 (8) | −0.0091 (8) | 0.0008 (8) |
| C10 | 0.0455 (11) | 0.0415 (10) | 0.0527 (11) | −0.0062 (8) | −0.0142 (9) | −0.0031 (8) |
| C11 | 0.0474 (10) | 0.0323 (9) | 0.0446 (10) | −0.0075 (7) | −0.0060 (8) | −0.0039 (7) |
| C12 | 0.0404 (9) | 0.0287 (8) | 0.0293 (8) | −0.0037 (7) | 0.0013 (7) | −0.0004 (6) |
| C13 | 0.0451 (10) | 0.0274 (8) | 0.0432 (10) | −0.0016 (7) | −0.0041 (8) | −0.0038 (7) |
| C14 | 0.0343 (9) | 0.0268 (8) | 0.0416 (9) | −0.0028 (6) | −0.0057 (7) | −0.0012 (7) |
| C15 | 0.0490 (11) | 0.0273 (8) | 0.0497 (11) | −0.0032 (7) | 0.0008 (8) | 0.0021 (7) |
| C16 | 0.0668 (13) | 0.0393 (10) | 0.0462 (11) | −0.0011 (9) | 0.0083 (10) | 0.0084 (8) |
| C17 | 0.0665 (13) | 0.0398 (10) | 0.0414 (10) | 0.0027 (9) | 0.0042 (9) | −0.0033 (8) |
| C1A | 0.0366 (10) | 0.0529 (11) | 0.0465 (11) | 0.0030 (8) | −0.0043 (8) | 0.0057 (9) |
| C2A | 0.0727 (15) | 0.0602 (14) | 0.0555 (13) | −0.0088 (12) | 0.0233 (11) | 0.0015 (10) |
| C3A | 0.0736 (16) | 0.0576 (14) | 0.0583 (14) | 0.0000 (12) | 0.0213 (12) | −0.0067 (11) |
| C4A | 0.0478 (11) | 0.0427 (11) | 0.0570 (12) | 0.0091 (9) | 0.0008 (9) | 0.0079 (9) |
| C5A | 0.120 (2) | 0.0620 (15) | 0.0465 (13) | −0.0132 (15) | 0.0164 (14) | 0.0118 (11) |
| C6A | 0.111 (2) | 0.0629 (15) | 0.0436 (12) | −0.0113 (14) | 0.0155 (13) | −0.0026 (11) |
| S1—O2 | 1.4417 (16) | C7—H7A | 0.9700 |
| S1—O3 | 1.4495 (15) | C7—H7B | 0.9700 |
| S1—O1 | 1.4501 (15) | C8—C9 | 1.364 (3) |
| S1—C8 | 1.7900 (17) | C8—C12 | 1.432 (2) |
| S2—O4 | 1.4496 (17) | C9—C10 | 1.407 (3) |
| S2—O5 | 1.4507 (17) | C9—H9 | 0.9300 |
| S2—O6 | 1.4531 (17) | C10—C11i | 1.360 (3) |
| S2—C13 | 1.7759 (17) | C10—H10 | 0.9300 |
| N1—C4 | 1.470 (2) | C11—C10i | 1.360 (3) |
| N1—H1A | 0.8900 | C11—C12 | 1.418 (3) |
| N1—H1B | 0.8900 | C11—H11 | 0.9300 |
| N1—H1C | 0.8900 | C12—C12i | 1.431 (3) |
| N1A—C4A | 1.478 (3) | C13—C17 | 1.369 (3) |
| N1A—H1A1 | 0.8900 | C13—C14 | 1.428 (2) |
| N1A—H1A2 | 0.8900 | C14—C15 | 1.419 (3) |
| N1A—H1A3 | 0.8900 | C14—C14ii | 1.431 (3) |
| O1W—H1WA | 0.860 (10) | C15—C16 | 1.359 (3) |
| O1W—H1WB | 0.854 (10) | C15—H15 | 0.9300 |
| O2W—H2WA | 0.847 (10) | C16—C17ii | 1.401 (3) |
| O2W—H2WB | 0.840 (10) | C16—H16 | 0.9300 |
| C1—C2 | 1.389 (3) | C17—C16ii | 1.401 (3) |
| C1—C6 | 1.399 (3) | C17—H17 | 0.9300 |
| C1—C7 | 1.510 (3) | C1A—C2A | 1.376 (3) |
| C2—C3 | 1.382 (3) | C1A—C6A | 1.379 (3) |
| C2—H2 | 0.9300 | C2A—C3A | 1.379 (3) |
| C3—C4 | 1.375 (3) | C2A—H2A | 0.9300 |
| C3—H3 | 0.9300 | C3A—C4A | 1.366 (3) |
| C4—C5 | 1.378 (3) | C3A—H3A | 0.9300 |
| C5—C6 | 1.379 (3) | C4A—C5A | 1.358 (3) |
| C5—H5 | 0.9300 | C5A—C6A | 1.384 (4) |
| C6—H6 | 0.9300 | C5A—H5A | 0.9300 |
| C7—C1A | 1.512 (3) | C6A—H6A | 0.9300 |
| O2—S1—O3 | 112.14 (10) | H7A—C7—H7B | 107.9 |
| O2—S1—O1 | 113.15 (10) | C9—C8—C12 | 120.94 (16) |
| O3—S1—O1 | 112.19 (10) | C9—C8—S1 | 118.27 (14) |
| O2—S1—C8 | 106.96 (8) | C12—C8—S1 | 120.78 (13) |
| O3—S1—C8 | 106.27 (9) | C8—C9—C10 | 120.28 (17) |
| O1—S1—C8 | 105.51 (8) | C8—C9—H9 | 119.9 |
| O4—S2—O5 | 113.54 (11) | C10—C9—H9 | 119.9 |
| O4—S2—O6 | 111.67 (11) | C11i—C10—C9 | 120.71 (18) |
| O5—S2—O6 | 111.49 (11) | C11i—C10—H10 | 119.6 |
| O4—S2—C13 | 107.67 (9) | C9—C10—H10 | 119.6 |
| O5—S2—C13 | 106.25 (9) | C10i—C11—C12 | 121.09 (17) |
| O6—S2—C13 | 105.67 (9) | C10i—C11—H11 | 119.5 |
| C4—N1—H1A | 109.5 | C12—C11—H11 | 119.5 |
| C4—N1—H1B | 109.5 | C11—C12—C12i | 118.75 (19) |
| H1A—N1—H1B | 109.5 | C11—C12—C8 | 123.03 (15) |
| C4—N1—H1C | 109.5 | C12i—C12—C8 | 118.22 (19) |
| H1A—N1—H1C | 109.5 | C17—C13—C14 | 121.41 (16) |
| H1B—N1—H1C | 109.5 | C17—C13—S2 | 117.57 (14) |
| C4A—N1A—H1A1 | 109.5 | C14—C13—S2 | 120.91 (13) |
| C4A—N1A—H1A2 | 109.5 | C15—C14—C13 | 123.46 (15) |
| H1A1—N1A—H1A2 | 109.5 | C15—C14—C14ii | 118.9 (2) |
| C4A—N1A—H1A3 | 109.5 | C13—C14—C14ii | 117.66 (19) |
| H1A1—N1A—H1A3 | 109.5 | C16—C15—C14 | 121.31 (17) |
| H1A2—N1A—H1A3 | 109.5 | C16—C15—H15 | 119.3 |
| H1WA—O1W—H1WB | 103.5 (14) | C14—C15—H15 | 119.3 |
| H2WA—O2W—H2WB | 106.2 (15) | C15—C16—C17ii | 120.51 (18) |
| C2—C1—C6 | 117.94 (19) | C15—C16—H16 | 119.7 |
| C2—C1—C7 | 121.48 (18) | C17ii—C16—H16 | 119.7 |
| C6—C1—C7 | 120.57 (19) | C13—C17—C16ii | 120.20 (18) |
| C3—C2—C1 | 121.54 (18) | C13—C17—H17 | 119.9 |
| C3—C2—H2 | 119.2 | C16ii—C17—H17 | 119.9 |
| C1—C2—H2 | 119.2 | C2A—C1A—C6A | 116.8 (2) |
| C4—C3—C2 | 118.83 (19) | C2A—C1A—C7 | 122.09 (19) |
| C4—C3—H3 | 120.6 | C6A—C1A—C7 | 121.1 (2) |
| C2—C3—H3 | 120.6 | C1A—C2A—C3A | 122.3 (2) |
| C3—C4—C5 | 121.45 (18) | C1A—C2A—H2A | 118.8 |
| C3—C4—N1 | 119.68 (18) | C3A—C2A—H2A | 118.8 |
| C5—C4—N1 | 118.87 (17) | C4A—C3A—C2A | 119.3 (2) |
| C4—C5—C6 | 119.20 (18) | C4A—C3A—H3A | 120.4 |
| C4—C5—H5 | 120.4 | C2A—C3A—H3A | 120.4 |
| C6—C5—H5 | 120.4 | C5A—C4A—C3A | 120.2 (2) |
| C5—C6—C1 | 121.03 (19) | C5A—C4A—N1A | 119.9 (2) |
| C5—C6—H6 | 119.5 | C3A—C4A—N1A | 119.9 (2) |
| C1—C6—H6 | 119.5 | C4A—C5A—C6A | 120.0 (2) |
| C1—C7—C1A | 112.23 (16) | C4A—C5A—H5A | 120.0 |
| C1—C7—H7A | 109.2 | C6A—C5A—H5A | 120.0 |
| C1A—C7—H7A | 109.2 | C1A—C6A—C5A | 121.5 (2) |
| C1—C7—H7B | 109.2 | C1A—C6A—H6A | 119.3 |
| C1A—C7—H7B | 109.2 | C5A—C6A—H6A | 119.3 |
| Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+1, −y, −z. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H1B···O1iii | 0.89 | 1.91 | 2.770 (2) | 162 |
| N1A—H1A1···O5iv | 0.89 | 2.03 | 2.897 (3) | 163 |
| N1—H1C···O1Wiii | 0.89 | 2.07 | 2.948 (3) | 167 |
| N1A—H1A2···O2Wv | 0.89 | 1.86 | 2.739 (3) | 171 |
| N1A—H1A3···O1Wv | 0.89 | 1.95 | 2.807 (3) | 161 |
| O1W—H1WA···O4iii | 0.860 (10) | 1.801 (10) | 2.645 (2) | 166 (2) |
| O1W—H1WB···O6vi | 0.854 (10) | 1.957 (11) | 2.807 (2) | 174 (3) |
| N1—H1A···O2 | 0.89 | 2.46 | 3.007 (2) | 120 |
| N1—H1A···O5 | 0.89 | 2.47 | 2.996 (2) | 118 |
| N1—H1A···O3 | 0.89 | 2.49 | 3.125 (3) | 129 |
| O2W—H2WA···O2iii | 0.847 (10) | 2.68 (3) | 3.072 (3) | 110 (2) |
| Symmetry codes: (iii) −x+1, −y+1, −z+1; (iv) x, y+1, z; (v) −x, −y+2, −z+1; (vi) x, y, z+1. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H1B···O1i | 0.89 | 1.91 | 2.770 (2) | 162 |
| N1A—H1A1···O5ii | 0.89 | 2.03 | 2.897 (3) | 163 |
| N1—H1C···O1Wi | 0.89 | 2.07 | 2.948 (3) | 167 |
| N1A—H1A2···O2Wiii | 0.89 | 1.86 | 2.739 (3) | 171 |
| N1A—H1A3···O1Wiii | 0.89 | 1.95 | 2.807 (3) | 161 |
| O1W—H1WA···O4i | 0.860 (10) | 1.801 (10) | 2.645 (2) | 166 (2) |
| O1W—H1WB···O6iv | 0.854 (10) | 1.957 (11) | 2.807 (2) | 174 (3) |
| Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, y+1, z; (iii) −x, −y+2, −z+1; (iv) x, y, z+1. |
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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 complex, (I), consists of one crystallographically independent 4,4'-diphenylmethylendiammonium dication, two water molecules and two independent half naphthalene-1,5-disulfonate dianions. In the dication, the dihedral angle between benzene rings is 74.67 (6)°, and central C1—C7—C1A angle is 112.23 (16)° (Fig. 1). Each dianion is placed on an inversion centre. The 4,4'-diphenylmethylendiammonium dication interact with two naphthalene-1,5-disulfonate dianions through N—H···O hydrogen bonds. These units are further linked by water molecules into an infinite three-dimensional framework by hydrogen bonds (Fig. 2).