Acta Cryst. (2008). E64, o2277 [ doi:10.1107/S1600536808035526 ]
The title compound, C11H9N3O4S·H2O, contains both an acid and a base centre and displays a zwitterionic structure. There are two independent molecules and two water molecules in the asymmetric unit. The dihedral angles between the benzene ring and the pyridinium ring are 109.7 (1) and 110.7 (1)°. The dihedral angles between the nitro group and the benzene ring are 116.1 (2) and 116.7 (1)°. The crystal structure is stabilized by N-H
O, O-HN and O-HO hydrogen bonds.
A solution of 2-nitrobenzenesulfonyl chloride (2.2 g, 10 mmol) in CH2Cl2 (10 ml) was added dropwise to a suspension of 4-aminopyridine (0.9 g, 10 mmol) in CH2Cl2 (10 ml) at room temperature with stirring. The reaction mixture was stirred overnight. The yellow solid obtained was washed with warm water to obtain the title compound in a yield of 55.7%. A colorless single crystal suitable for X-ray analysis was obtained by slow evaporation of an NaOH (10%) solution at room temperature over a period of a week.
The N-bound H atoms were located in a difference map and their coordinates were refined with Uiso(H) = 1.2Ueq(N). The C-bound H atoms were positioned geometrically (C—H = 0.93 Å) and refined as riding with Uiso(H) = 1.2Ueq(C). The Flack test results are ambiguous because of the presence of merohedral twin. The water O-bound H atoms were refined freely, but the O—H distances were restrained to 0.85 (1) Å, and the water HA···HB distance to 1.45 (1) Å.
Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); 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 (Sheldrick, 2008).
![[Figure 1]](./hg2431fig1thm.gif)
| Fig. 1. View of the molecule of title compound showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 35% probability level (arbitrary spheres for the H atoms). |
| C11H9N3O4S·H2O | F(000) = 616 |
| Mr = 297.29 | Dx = 1.557 Mg m−3 |
| Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: P 2yb | Cell parameters from 4439 reflections |
| a = 8.7206 (17) Å | θ = 2.4–27.5° |
| b = 11.972 (2) Å | µ = 0.28 mm−1 |
| c = 12.743 (3) Å | T = 113 K |
| β = 107.65 (3)° | Block, colourless |
| V = 1267.8 (4) Å3 | 0.14 × 0.10 × 0.04 mm |
| Z = 4 |
| Rigaku Saturn diffractometer | 4633 independent reflections |
| Radiation source: rotating anode | 3587 reflections with I > 2σ(I) |
| confocal | Rint = 0.033 |
| ω scans | θmax = 27.5°, θmin = 1.7° |
| Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005) | h = −11→11 |
| Tmin = 0.962, Tmax = 0.989 | k = −12→15 |
| 10348 measured reflections | l = −16→16 |
| 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)] = 0.032 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.090 | w = 1/[σ2(Fo2) + (0.0539P)2] where P = (Fo2 + 2Fc2)/3 |
| S = 1.03 | (Δ/σ)max = 0.002 |
| 4633 reflections | Δρmax = 0.22 e Å−3 |
| 385 parameters | Δρmin = −0.40 e Å−3 |
| 9 restraints | Absolute structure: Flack (1983), with how many Friedel pairs? |
| Primary atom site location: structure-invariant direct methods | Flack parameter: 0.52 (6) |
| C11H9N3O4S·H2O | V = 1267.8 (4) Å3 |
| Mr = 297.29 | Z = 4 |
| Monoclinic, P21 | Mo Kα radiation |
| a = 8.7206 (17) Å | µ = 0.28 mm−1 |
| b = 11.972 (2) Å | T = 113 K |
| c = 12.743 (3) Å | 0.14 × 0.10 × 0.04 mm |
| β = 107.65 (3)° |
| Rigaku Saturn diffractometer | 3587 reflections with I > 2σ(I) |
| Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005) | Rint = 0.033 |
| Tmin = 0.962, Tmax = 0.989 | θmax = 27.5° |
| 10348 measured reflections | Standard reflections: 0 |
| 4633 independent reflections |
| R[F2 > 2σ(F2)] = 0.032 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.090 | Δρmax = 0.22 e Å−3 |
| S = 1.03 | Δρmin = −0.40 e Å−3 |
| 4633 reflections | Absolute structure: Flack (1983), with how many Friedel pairs? |
| 385 parameters | Flack parameter: 0.52 (6) |
| 9 restraints |
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 | 0.54299 (7) | 0.49945 (5) | 0.75574 (5) | 0.01423 (14) | |
| S2 | 1.01577 (7) | 0.25356 (5) | 0.35546 (5) | 0.01307 (14) | |
| O1 | 0.36887 (19) | 0.49815 (17) | 0.72910 (14) | 0.0177 (4) | |
| O2 | 0.6116 (2) | 0.59540 (15) | 0.71745 (16) | 0.0187 (4) | |
| O3 | 0.4219 (3) | 0.29003 (18) | 0.87441 (18) | 0.0318 (5) | |
| O4 | 0.2777 (2) | 0.4008 (2) | 0.94108 (18) | 0.0326 (5) | |
| O5 | 0.9524 (2) | 0.15286 (15) | 0.38857 (15) | 0.0165 (4) | |
| O6 | 1.1904 (2) | 0.26159 (18) | 0.38501 (16) | 0.0182 (4) | |
| O7 | 1.1373 (3) | 0.46983 (18) | 0.24125 (19) | 0.0334 (5) | |
| O8 | 1.2807 (2) | 0.3638 (2) | 0.16880 (18) | 0.0371 (6) | |
| N1 | 1.0324 (3) | 0.2999 (2) | 0.67719 (19) | 0.0185 (5) | |
| N2 | 0.5920 (2) | 0.38299 (18) | 0.71702 (19) | 0.0146 (5) | |
| N3 | 0.4050 (3) | 0.3727 (2) | 0.9245 (2) | 0.0217 (5) | |
| N4 | 0.5077 (3) | 0.4240 (2) | 0.43389 (18) | 0.0179 (5) | |
| N5 | 0.9564 (2) | 0.36491 (18) | 0.39696 (18) | 0.0141 (5) | |
| N6 | 1.1564 (3) | 0.3888 (2) | 0.18846 (19) | 0.0230 (6) | |
| C1 | 0.7414 (3) | 0.3615 (2) | 0.7078 (2) | 0.0132 (5) | |
| C2 | 0.7644 (3) | 0.2549 (2) | 0.6690 (2) | 0.0167 (5) | |
| H2 | 0.6813 | 0.2029 | 0.6537 | 0.020* | |
| C3 | 0.9100 (3) | 0.2265 (2) | 0.6532 (2) | 0.0188 (6) | |
| H3 | 0.9231 | 0.1563 | 0.6259 | 0.023* | |
| C4 | 1.0168 (3) | 0.4019 (2) | 0.7153 (2) | 0.0179 (6) | |
| H4 | 1.1030 | 0.4513 | 0.7304 | 0.021* | |
| C5 | 0.8752 (3) | 0.4350 (2) | 0.7325 (2) | 0.0169 (6) | |
| H5 | 0.8672 | 0.5058 | 0.7604 | 0.020* | |
| C6 | 0.6158 (3) | 0.5053 (3) | 0.9027 (2) | 0.0148 (5) | |
| C7 | 0.7441 (3) | 0.5753 (2) | 0.9531 (2) | 0.0189 (6) | |
| H7 | 0.7936 | 0.6156 | 0.9100 | 0.023* | |
| C8 | 0.7996 (3) | 0.5858 (2) | 1.0674 (2) | 0.0240 (6) | |
| H8 | 0.8857 | 0.6329 | 1.0999 | 0.029* | |
| C9 | 0.7271 (3) | 0.5264 (3) | 1.1326 (2) | 0.0245 (7) | |
| H9 | 0.7656 | 0.5325 | 1.2089 | 0.029* | |
| C10 | 0.5978 (3) | 0.4582 (2) | 1.0843 (2) | 0.0208 (6) | |
| H10 | 0.5469 | 0.4197 | 1.1277 | 0.025* | |
| C11 | 0.5441 (3) | 0.4472 (2) | 0.9712 (2) | 0.0162 (6) | |
| C12 | 0.8049 (3) | 0.3782 (2) | 0.4049 (2) | 0.0120 (5) | |
| C13 | 0.7734 (3) | 0.4806 (2) | 0.4510 (2) | 0.0163 (6) | |
| H13 | 0.8534 | 0.5347 | 0.4722 | 0.020* | |
| C14 | 0.6264 (3) | 0.4998 (2) | 0.4642 (2) | 0.0181 (5) | |
| H14 | 0.6078 | 0.5669 | 0.4949 | 0.022* | |
| C15 | 0.5302 (3) | 0.3265 (2) | 0.3884 (2) | 0.0165 (5) | |
| H15 | 0.4464 | 0.2752 | 0.3672 | 0.020* | |
| C16 | 0.6767 (3) | 0.3014 (2) | 0.3725 (2) | 0.0136 (5) | |
| H16 | 0.6905 | 0.2339 | 0.3405 | 0.016* | |
| C17 | 0.9459 (3) | 0.2526 (2) | 0.2084 (2) | 0.0145 (5) | |
| C18 | 0.8167 (3) | 0.1850 (2) | 0.1552 (2) | 0.0179 (6) | |
| H18 | 0.7672 | 0.1423 | 0.1967 | 0.021* | |
| C19 | 0.7603 (3) | 0.1799 (2) | 0.0417 (2) | 0.0229 (6) | |
| H19 | 0.6723 | 0.1349 | 0.0080 | 0.027* | |
| C20 | 0.8324 (3) | 0.2406 (3) | −0.0223 (2) | 0.0245 (7) | |
| H20 | 0.7933 | 0.2365 | −0.0987 | 0.029* | |
| C21 | 0.9631 (3) | 0.3074 (2) | 0.0276 (2) | 0.0195 (6) | |
| H21 | 1.0141 | 0.3476 | −0.0146 | 0.023* | |
| C22 | 1.0173 (3) | 0.3137 (2) | 0.1415 (2) | 0.0157 (6) | |
| O9 | 0.2408 (2) | 0.50194 (18) | 0.48520 (16) | 0.0183 (4) | |
| O10 | 0.6923 (2) | 0.74683 (18) | 0.37557 (18) | 0.0203 (4) | |
| H1A | 1.127 (3) | 0.280 (3) | 0.665 (3) | 0.054 (11)* | |
| H4A | 0.411 (2) | 0.441 (2) | 0.444 (2) | 0.021 (8)* | |
| H9A | 0.260 (3) | 0.500 (3) | 0.5558 (8) | 0.047 (11)* | |
| H9B | 0.160 (2) | 0.460 (2) | 0.4517 (18) | 0.024 (9)* | |
| H10A | 0.719 (4) | 0.751 (4) | 0.4468 (8) | 0.11 (2)* | |
| H10B | 0.601 (2) | 0.780 (3) | 0.346 (2) | 0.034 (10)* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| S1 | 0.0127 (3) | 0.0152 (3) | 0.0156 (3) | 0.0016 (3) | 0.0055 (2) | 0.0026 (3) |
| S2 | 0.0098 (3) | 0.0162 (3) | 0.0138 (3) | 0.0013 (3) | 0.0044 (2) | 0.0012 (3) |
| O1 | 0.0119 (8) | 0.0220 (10) | 0.0201 (10) | 0.0049 (9) | 0.0064 (7) | 0.0009 (9) |
| O2 | 0.0242 (10) | 0.0133 (9) | 0.0209 (11) | 0.0000 (8) | 0.0102 (9) | 0.0042 (8) |
| O3 | 0.0376 (12) | 0.0285 (12) | 0.0288 (13) | −0.0115 (10) | 0.0095 (10) | −0.0019 (10) |
| O4 | 0.0157 (9) | 0.0515 (15) | 0.0329 (13) | −0.0051 (10) | 0.0109 (9) | 0.0064 (12) |
| O5 | 0.0194 (10) | 0.0153 (9) | 0.0158 (10) | 0.0043 (8) | 0.0067 (8) | 0.0053 (8) |
| O6 | 0.0099 (8) | 0.0269 (11) | 0.0190 (10) | 0.0008 (9) | 0.0061 (7) | 0.0016 (9) |
| O7 | 0.0378 (13) | 0.0292 (13) | 0.0329 (13) | −0.0111 (10) | 0.0101 (11) | −0.0060 (10) |
| O8 | 0.0180 (10) | 0.0689 (18) | 0.0274 (13) | −0.0077 (11) | 0.0114 (10) | 0.0055 (12) |
| N1 | 0.0135 (11) | 0.0249 (12) | 0.0184 (12) | 0.0064 (10) | 0.0067 (9) | 0.0022 (10) |
| N2 | 0.0116 (10) | 0.0147 (11) | 0.0196 (12) | 0.0000 (9) | 0.0078 (9) | −0.0001 (9) |
| N3 | 0.0209 (12) | 0.0263 (14) | 0.0176 (13) | −0.0040 (11) | 0.0057 (10) | 0.0071 (10) |
| N4 | 0.0148 (11) | 0.0224 (13) | 0.0179 (12) | 0.0020 (10) | 0.0072 (9) | 0.0009 (10) |
| N5 | 0.0108 (10) | 0.0177 (11) | 0.0144 (11) | −0.0028 (9) | 0.0046 (9) | −0.0035 (9) |
| N6 | 0.0193 (12) | 0.0354 (15) | 0.0146 (12) | −0.0067 (11) | 0.0054 (10) | 0.0064 (11) |
| C1 | 0.0123 (11) | 0.0178 (13) | 0.0100 (13) | 0.0024 (10) | 0.0042 (10) | 0.0041 (10) |
| C2 | 0.0166 (11) | 0.0179 (12) | 0.0164 (13) | −0.0044 (12) | 0.0062 (10) | 0.0015 (12) |
| C3 | 0.0177 (13) | 0.0173 (14) | 0.0217 (15) | 0.0033 (11) | 0.0062 (11) | −0.0025 (11) |
| C4 | 0.0133 (12) | 0.0214 (14) | 0.0181 (14) | −0.0009 (11) | 0.0035 (10) | 0.0014 (12) |
| C5 | 0.0145 (12) | 0.0147 (13) | 0.0211 (15) | 0.0009 (11) | 0.0048 (11) | −0.0006 (11) |
| C6 | 0.0151 (12) | 0.0134 (13) | 0.0166 (13) | 0.0032 (12) | 0.0059 (10) | 0.0000 (12) |
| C7 | 0.0206 (13) | 0.0143 (13) | 0.0224 (15) | −0.0036 (11) | 0.0075 (12) | 0.0006 (11) |
| C8 | 0.0252 (15) | 0.0225 (15) | 0.0224 (16) | −0.0067 (13) | 0.0040 (13) | −0.0035 (12) |
| C9 | 0.0255 (14) | 0.0278 (16) | 0.0184 (15) | 0.0041 (13) | 0.0038 (12) | −0.0030 (12) |
| C10 | 0.0236 (14) | 0.0239 (15) | 0.0178 (15) | 0.0041 (12) | 0.0106 (12) | 0.0047 (12) |
| C11 | 0.0103 (11) | 0.0175 (13) | 0.0217 (15) | 0.0013 (10) | 0.0062 (11) | 0.0027 (11) |
| C12 | 0.0152 (12) | 0.0125 (12) | 0.0083 (12) | 0.0024 (10) | 0.0038 (10) | 0.0017 (10) |
| C13 | 0.0168 (12) | 0.0141 (13) | 0.0183 (14) | −0.0048 (11) | 0.0060 (11) | −0.0026 (11) |
| C14 | 0.0225 (13) | 0.0147 (12) | 0.0186 (13) | −0.0018 (12) | 0.0087 (11) | −0.0020 (12) |
| C15 | 0.0136 (12) | 0.0198 (13) | 0.0173 (14) | 0.0002 (11) | 0.0066 (11) | −0.0031 (11) |
| C16 | 0.0093 (11) | 0.0150 (12) | 0.0173 (14) | −0.0026 (10) | 0.0051 (10) | −0.0032 (11) |
| C17 | 0.0160 (12) | 0.0150 (12) | 0.0119 (13) | 0.0007 (12) | 0.0033 (10) | −0.0004 (11) |
| C18 | 0.0193 (13) | 0.0163 (14) | 0.0198 (15) | −0.0015 (12) | 0.0084 (12) | 0.0037 (12) |
| C19 | 0.0262 (15) | 0.0190 (15) | 0.0202 (15) | −0.0061 (13) | 0.0022 (12) | 0.0005 (12) |
| C20 | 0.0322 (15) | 0.0275 (16) | 0.0115 (14) | 0.0032 (14) | 0.0033 (12) | −0.0006 (13) |
| C21 | 0.0193 (13) | 0.0221 (15) | 0.0205 (15) | 0.0031 (12) | 0.0110 (12) | 0.0049 (12) |
| C22 | 0.0118 (11) | 0.0181 (14) | 0.0172 (14) | 0.0001 (11) | 0.0045 (11) | 0.0019 (11) |
| O9 | 0.0157 (9) | 0.0210 (10) | 0.0194 (11) | 0.0003 (9) | 0.0072 (8) | −0.0056 (10) |
| O10 | 0.0170 (9) | 0.0221 (10) | 0.0215 (11) | 0.0022 (9) | 0.0057 (8) | 0.0043 (10) |
| S1—O2 | 1.4464 (19) | C6—C11 | 1.403 (3) |
| S1—O1 | 1.4521 (17) | C7—C8 | 1.394 (4) |
| S1—N2 | 1.581 (2) | C7—H7 | 0.9300 |
| S1—C6 | 1.787 (3) | C8—C9 | 1.383 (4) |
| S2—O5 | 1.4416 (19) | C8—H8 | 0.9300 |
| S2—O6 | 1.4568 (17) | C9—C10 | 1.377 (4) |
| S2—N5 | 1.578 (2) | C9—H9 | 0.9300 |
| S2—C17 | 1.787 (3) | C10—C11 | 1.380 (4) |
| O3—N3 | 1.211 (3) | C10—H10 | 0.9300 |
| O4—N3 | 1.237 (3) | C12—C16 | 1.409 (3) |
| O7—N6 | 1.221 (3) | C12—C13 | 1.421 (3) |
| O8—N6 | 1.221 (3) | C13—C14 | 1.362 (3) |
| N1—C4 | 1.336 (4) | C13—H13 | 0.9300 |
| N1—C3 | 1.345 (3) | C14—H14 | 0.9300 |
| N1—H1A | 0.918 (10) | C15—C16 | 1.385 (3) |
| N2—C1 | 1.367 (3) | C15—H15 | 0.9300 |
| N3—C11 | 1.478 (3) | C16—H16 | 0.9300 |
| N4—C14 | 1.342 (3) | C17—C18 | 1.386 (4) |
| N4—C15 | 1.344 (3) | C17—C22 | 1.404 (3) |
| N4—H4A | 0.913 (10) | C18—C19 | 1.380 (4) |
| N5—C12 | 1.365 (3) | C18—H18 | 0.9300 |
| N6—C22 | 1.482 (3) | C19—C20 | 1.379 (4) |
| C1—C2 | 1.405 (4) | C19—H19 | 0.9300 |
| C1—C5 | 1.419 (4) | C20—C21 | 1.380 (4) |
| C2—C3 | 1.387 (3) | C20—H20 | 0.9300 |
| C2—H2 | 0.9300 | C21—C22 | 1.385 (4) |
| C3—H3 | 0.9300 | C21—H21 | 0.9300 |
| C4—C5 | 1.376 (3) | O9—H9A | 0.864 (10) |
| C4—H4 | 0.9300 | O9—H9B | 0.867 (10) |
| C5—H5 | 0.9300 | O10—H10A | 0.867 (10) |
| C6—C7 | 1.389 (4) | O10—H10B | 0.870 (10) |
| O2—S1—O1 | 116.08 (11) | C9—C8—C7 | 120.3 (3) |
| O2—S1—N2 | 114.62 (10) | C9—C8—H8 | 119.9 |
| O1—S1—N2 | 106.27 (11) | C7—C8—H8 | 119.9 |
| O2—S1—C6 | 105.68 (13) | C10—C9—C8 | 119.8 (3) |
| O1—S1—C6 | 105.03 (11) | C10—C9—H9 | 120.1 |
| N2—S1—C6 | 108.55 (13) | C8—C9—H9 | 120.1 |
| O5—S2—O6 | 116.29 (11) | C9—C10—C11 | 119.8 (3) |
| O5—S2—N5 | 114.48 (10) | C9—C10—H10 | 120.1 |
| O6—S2—N5 | 106.33 (12) | C11—C10—H10 | 120.1 |
| O5—S2—C17 | 105.23 (12) | C10—C11—C6 | 121.9 (3) |
| O6—S2—C17 | 105.61 (11) | C10—C11—N3 | 117.1 (2) |
| N5—S2—C17 | 108.33 (12) | C6—C11—N3 | 121.0 (2) |
| C4—N1—C3 | 121.3 (2) | N5—C12—C16 | 127.0 (2) |
| C4—N1—H1A | 120 (2) | N5—C12—C13 | 116.4 (2) |
| C3—N1—H1A | 119 (2) | C16—C12—C13 | 116.6 (2) |
| C1—N2—S1 | 123.21 (19) | C14—C13—C12 | 120.2 (2) |
| O3—N3—O4 | 124.9 (3) | C14—C13—H13 | 119.9 |
| O3—N3—C11 | 119.3 (2) | C12—C13—H13 | 119.9 |
| O4—N3—C11 | 115.9 (2) | N4—C14—C13 | 121.6 (3) |
| C14—N4—C15 | 120.7 (2) | N4—C14—H14 | 119.2 |
| C14—N4—H4A | 118.3 (19) | C13—C14—H14 | 119.2 |
| C15—N4—H4A | 121.0 (19) | N4—C15—C16 | 120.9 (2) |
| C12—N5—S2 | 123.16 (18) | N4—C15—H15 | 119.6 |
| O7—N6—O8 | 125.8 (3) | C16—C15—H15 | 119.6 |
| O7—N6—C22 | 118.2 (2) | C15—C16—C12 | 120.0 (2) |
| O8—N6—C22 | 115.9 (2) | C15—C16—H16 | 120.0 |
| N2—C1—C2 | 116.3 (2) | C12—C16—H16 | 120.0 |
| N2—C1—C5 | 127.2 (2) | C18—C17—C22 | 116.9 (2) |
| C2—C1—C5 | 116.5 (2) | C18—C17—S2 | 119.0 (2) |
| C3—C2—C1 | 120.6 (2) | C22—C17—S2 | 124.1 (2) |
| C3—C2—H2 | 119.7 | C19—C18—C17 | 121.1 (2) |
| C1—C2—H2 | 119.7 | C19—C18—H18 | 119.4 |
| N1—C3—C2 | 120.3 (2) | C17—C18—H18 | 119.4 |
| N1—C3—H3 | 119.8 | C20—C19—C18 | 121.0 (3) |
| C2—C3—H3 | 119.8 | C20—C19—H19 | 119.5 |
| N1—C4—C5 | 121.1 (3) | C18—C19—H19 | 119.5 |
| N1—C4—H4 | 119.5 | C19—C20—C21 | 119.6 (3) |
| C5—C4—H4 | 119.5 | C19—C20—H20 | 120.2 |
| C4—C5—C1 | 120.2 (2) | C21—C20—H20 | 120.2 |
| C4—C5—H5 | 119.9 | C20—C21—C22 | 119.1 (3) |
| C1—C5—H5 | 119.9 | C20—C21—H21 | 120.4 |
| C7—C6—C11 | 117.3 (2) | C22—C21—H21 | 120.4 |
| C7—C6—S1 | 119.3 (2) | C21—C22—C17 | 122.3 (2) |
| C11—C6—S1 | 123.3 (2) | C21—C22—N6 | 115.7 (2) |
| C6—C7—C8 | 120.9 (3) | C17—C22—N6 | 122.0 (2) |
| C6—C7—H7 | 119.6 | H9A—O9—H9B | 111.6 (16) |
| C8—C7—H7 | 119.6 | H10A—O10—H10B | 110.7 (16) |
| O2—S1—N2—C1 | 36.7 (2) | O4—N3—C11—C10 | 62.9 (3) |
| O1—S1—N2—C1 | 166.3 (2) | O3—N3—C11—C6 | 64.4 (4) |
| C6—S1—N2—C1 | −81.2 (2) | O4—N3—C11—C6 | −116.0 (3) |
| O5—S2—N5—C12 | −36.0 (2) | S2—N5—C12—C16 | −4.2 (4) |
| O6—S2—N5—C12 | −165.8 (2) | S2—N5—C12—C13 | 175.7 (2) |
| C17—S2—N5—C12 | 81.0 (2) | N5—C12—C13—C14 | −178.5 (2) |
| S1—N2—C1—C2 | −178.07 (19) | C16—C12—C13—C14 | 1.4 (4) |
| S1—N2—C1—C5 | 1.5 (4) | C15—N4—C14—C13 | −0.6 (4) |
| N2—C1—C2—C3 | 177.8 (2) | C12—C13—C14—N4 | −0.4 (4) |
| C5—C1—C2—C3 | −1.9 (4) | C14—N4—C15—C16 | 0.6 (4) |
| C4—N1—C3—C2 | −0.8 (4) | N4—C15—C16—C12 | 0.4 (4) |
| C1—C2—C3—N1 | 1.4 (4) | N5—C12—C16—C15 | 178.5 (2) |
| C3—N1—C4—C5 | 0.7 (4) | C13—C12—C16—C15 | −1.3 (4) |
| N1—C4—C5—C1 | −1.2 (4) | O5—S2—C17—C18 | 18.6 (2) |
| N2—C1—C5—C4 | −177.8 (3) | O6—S2—C17—C18 | 142.2 (2) |
| C2—C1—C5—C4 | 1.8 (4) | N5—S2—C17—C18 | −104.2 (2) |
| O2—S1—C6—C7 | −14.8 (2) | O5—S2—C17—C22 | −159.0 (2) |
| O1—S1—C6—C7 | −138.0 (2) | O6—S2—C17—C22 | −35.5 (3) |
| N2—S1—C6—C7 | 108.6 (2) | N5—S2—C17—C22 | 78.1 (2) |
| O2—S1—C6—C11 | 161.6 (2) | C22—C17—C18—C19 | −1.0 (4) |
| O1—S1—C6—C11 | 38.3 (3) | S2—C17—C18—C19 | −178.8 (2) |
| N2—S1—C6—C11 | −75.0 (2) | C17—C18—C19—C20 | 1.1 (4) |
| C11—C6—C7—C8 | 0.6 (4) | C18—C19—C20—C21 | 0.1 (4) |
| S1—C6—C7—C8 | 177.2 (2) | C19—C20—C21—C22 | −1.2 (4) |
| C6—C7—C8—C9 | −0.1 (4) | C20—C21—C22—C17 | 1.3 (4) |
| C7—C8—C9—C10 | −1.1 (4) | C20—C21—C22—N6 | −179.0 (2) |
| C8—C9—C10—C11 | 1.7 (4) | C18—C17—C22—C21 | −0.2 (4) |
| C9—C10—C11—C6 | −1.2 (4) | S2—C17—C22—C21 | 177.5 (2) |
| C9—C10—C11—N3 | 180.0 (2) | C18—C17—C22—N6 | −179.9 (2) |
| C7—C6—C11—C10 | 0.0 (4) | S2—C17—C22—N6 | −2.2 (4) |
| S1—C6—C11—C10 | −176.4 (2) | O7—N6—C22—C21 | 116.6 (3) |
| C7—C6—C11—N3 | 178.8 (2) | O8—N6—C22—C21 | −62.4 (3) |
| S1—C6—C11—N3 | 2.4 (4) | O7—N6—C22—C17 | −63.7 (4) |
| O3—N3—C11—C10 | −116.7 (3) | O8—N6—C22—C17 | 117.3 (3) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N4—H4A···O9 | 0.91 (1) | 1.87 (1) | 2.764 (3) | 167 (3) |
| O9—H9A···O1 | 0.86 (1) | 2.12 (1) | 2.967 (3) | 166 (3) |
| N1—H1A···O10i | 0.92 (1) | 1.84 (1) | 2.757 (3) | 174 (4) |
| O9—H9B···N5ii | 0.87 (1) | 2.04 (1) | 2.901 (3) | 170 (2) |
| O9—H9B···O6ii | 0.87 (1) | 2.56 (2) | 3.125 (3) | 123 (2) |
| O10—H10A···O6iii | 0.87 (1) | 2.05 (1) | 2.914 (3) | 174 (4) |
| O10—H10B···N2iv | 0.87 (1) | 2.04 (1) | 2.902 (3) | 170 (3) |
| Symmetry codes: (i) −x+2, y−1/2, −z+1; (ii) x−1, y, z; (iii) −x+2, y+1/2, −z+1; (iv) −x+1, y+1/2, −z+1. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N4—H4A···O9 | 0.91 (1) | 1.87 (1) | 2.764 (3) | 167 (3) |
| O9—H9A···O1 | 0.86 (1) | 2.12 (1) | 2.967 (3) | 166 (3) |
| N1—H1A···O10i | 0.92 (1) | 1.84 (1) | 2.757 (3) | 174 (4) |
| O9—H9B···N5ii | 0.87 (1) | 2.04 (1) | 2.901 (3) | 170 (2) |
| O9—H9B···O6ii | 0.87 (1) | 2.56 (2) | 3.125 (3) | 123 (2) |
| O10—H10A···O6iii | 0.87 (1) | 2.05 (1) | 2.914 (3) | 174 (4) |
| O10—H10B···N2iv | 0.87 (1) | 2.04 (1) | 2.902 (3) | 170 (3) |
| Symmetry codes: (i) −x+2, y−1/2, −z+1; (ii) x−1, y, z; (iii) −x+2, y+1/2, −z+1; (iv) −x+1, y+1/2, −z+1. |
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.
Damiano, T., Morton, D. & Nelson, A. (2007). Org. Biomol. Chem. 5, 2735—2752.
Flack, H. D. (1983). Acta Cryst. A39, 876–881.
Li, J.-S., Chen, L.-G., Zhang, Y.-Y., Xu, Y.-J., Deng, Y., Zeng, T. & Huang, P.-M. (2007). J. Chem. Res. pp. 350–352.
Rigaku/MSC (2005). CrystalClear and CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Yu, H.-J. & Li, J.-S. (2007). Acta Cryst. E63, o3399.
Organic pyridinium salts have been widely used in the construction of supramolecular architectures (Damiano et al., 2007). As part of our ongoing studies of supramolecular chemistry involving the pyridinium rings (Li et al., 2007), the structure of the title compound was determined by X-ray diffraction. There are two independent molecules and two independent water molecules in the unit cell. In the cations of the title compound the short C—N distance [N2—C1 = 1.367 (3) Å and N5—C12 = 1.365 (3) Å] indicate the slight conjugation of the sulfonamide N with the pyridinium ring (Allen et al., 1987).
The dihedral angles between the benzene ring and the pyridinium ring are 109.7 (1)° and 110.7 (1)° respectively. And the dihedral angles between the nitro group and the benzene ring are 116.1 (2)° and 116.7 (1)° respectively. The crystal structure is stabilized by N—H···O hydrogen bonds.