Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801016841/ci6068sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801016841/ci6068Isup2.hkl |
CCDC reference: 176008
The synthesis of the title compound was carried out by heating under reflux for 10 min, 1 mmol quantities of 3,5-dinitrosalicylic acid and sulfanilamide (4-aminobenzenesulfonamide) in 30 ml of 80% ethanol/water. Crystals were obtained after partial room-temperature evaporation of solvent.
H atoms were located from a difference map and both positional and isotropic displacement parameters were refined. For H atoms: C—H range 0.88 (2)–0.96 (2) Å; N—H range 0.81 (3)–0.93 (3) Å, and the intramolecular O—H distance is 1.03 (4) Å.
Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: PROCESS DATA (Gable et al., 1994); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON for Windows (Spek, 1999).
C7H3N2O7+·C6H9N2O2S− | F(000) = 412 |
Mr = 400.33 | Dx = 1.702 Mg m−3 |
Triclinic, P1 | Melting point = 471–474 K |
a = 7.0167 (9) Å | Mo Kα radiation, λ = 0.71069 Å |
b = 9.137 (1) Å | Cell parameters from 25 reflections |
c = 12.430 (1) Å | θ = 12–15° |
α = 90.77 (1)° | µ = 0.27 mm−1 |
β = 99.736 (9)° | T = 293 K |
γ = 95.70 (1)° | Prismatic, yellow |
V = 781.17 (15) Å3 | 0.35 × 0.25 × 0.20 mm |
Z = 2 |
Nonius CAD-4 diffractometer | Rint = 0.010 |
Radiation source: fine-focus sealed tube | θmax = 27.5°, θmin = 2.2° |
Graphite monochromator | h = 0→9 |
ω–2θ scans | k = −11→11 |
3867 measured reflections | l = −16→15 |
3575 independent reflections | 3 standard reflections every 160 min |
3080 reflections with I > 2σ(I) | intensity decay: 5.0% |
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)] = 0.037 | All H-atom parameters refined |
wR(F2) = 0.098 | w = 1/[σ2(Fo2) + (0.0482P)2 + 0.3779P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.006 |
3575 reflections | Δρmax = 0.39 e Å−3 |
293 parameters | Δρmin = −0.35 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.008 (2) |
C7H3N2O7+·C6H9N2O2S− | γ = 95.70 (1)° |
Mr = 400.33 | V = 781.17 (15) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.0167 (9) Å | Mo Kα radiation |
b = 9.137 (1) Å | µ = 0.27 mm−1 |
c = 12.430 (1) Å | T = 293 K |
α = 90.77 (1)° | 0.35 × 0.25 × 0.20 mm |
β = 99.736 (9)° |
Nonius CAD-4 diffractometer | Rint = 0.010 |
3867 measured reflections | 3 standard reflections every 160 min |
3575 independent reflections | intensity decay: 5.0% |
3080 reflections with I > 2σ(I) |
R[F2 > 2σ(F2)] = 0.037 | 0 restraints |
wR(F2) = 0.098 | All H-atom parameters refined |
S = 1.05 | Δρmax = 0.39 e Å−3 |
3575 reflections | Δρmin = −0.35 e Å−3 |
293 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. Because of the quality of the diffraction data, both positional and isotropic thermal parameters for the hydrogen atoms were refined after location by difference methods. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.35087 (6) | 0.71792 (4) | 0.94734 (3) | 0.02694 (12) | |
O1 | 0.2139 (2) | 0.24127 (13) | 0.42861 (10) | 0.0380 (3) | |
O2 | 0.1911 (2) | 0.19643 (14) | 0.62114 (12) | 0.0462 (4) | |
O3 | 0.1827 (3) | 0.38115 (15) | 0.73562 (11) | 0.0501 (4) | |
O4 | 0.3104 (3) | 0.88515 (15) | 0.61647 (12) | 0.0499 (4) | |
O5 | 0.2881 (3) | 0.92742 (15) | 0.44514 (13) | 0.0649 (5) | |
O6 | 0.3404 (3) | 0.52808 (19) | 0.19908 (13) | 0.0713 (6) | |
O7 | 0.1673 (3) | 0.32814 (18) | 0.21878 (12) | 0.0630 (5) | |
O8 | 0.55495 (19) | 0.72510 (15) | 0.98855 (11) | 0.0394 (3) | |
O9 | 0.2929 (2) | 0.77867 (15) | 0.84179 (10) | 0.0393 (3) | |
N1 | 0.2535 (2) | 0.44434 (17) | 0.25418 (12) | 0.0358 (3) | |
N2 | 0.2931 (2) | 0.84362 (15) | 0.52100 (13) | 0.0341 (3) | |
N3 | 0.2456 (3) | 0.55353 (17) | 0.94170 (15) | 0.0367 (4) | |
N4 | −0.0079 (2) | 1.04475 (16) | 1.26713 (12) | 0.0285 (3) | |
C1 | 0.2325 (2) | 0.43951 (17) | 0.55606 (13) | 0.0255 (3) | |
C2 | 0.2308 (2) | 0.38119 (17) | 0.44778 (13) | 0.0259 (3) | |
C3 | 0.2539 (2) | 0.48888 (18) | 0.36743 (13) | 0.0272 (3) | |
C4 | 0.2773 (2) | 0.63791 (18) | 0.39093 (14) | 0.0282 (3) | |
C5 | 0.2768 (2) | 0.68640 (16) | 0.49655 (13) | 0.0265 (3) | |
C6 | 0.2549 (2) | 0.58874 (17) | 0.57955 (13) | 0.0265 (3) | |
C7 | 0.2017 (3) | 0.33762 (18) | 0.64612 (13) | 0.0305 (4) | |
C8 | 0.2444 (2) | 0.81196 (17) | 1.04360 (12) | 0.0258 (3) | |
C9 | 0.0450 (3) | 0.79465 (19) | 1.03839 (14) | 0.0314 (4) | |
C10 | −0.0368 (3) | 0.87180 (19) | 1.11212 (14) | 0.0312 (4) | |
C11 | 0.0826 (2) | 0.96653 (17) | 1.18838 (12) | 0.0252 (3) | |
C12 | 0.2803 (3) | 0.9870 (2) | 1.19299 (15) | 0.0349 (4) | |
C13 | 0.3625 (3) | 0.9076 (2) | 1.11989 (15) | 0.0356 (4) | |
H1 | 0.196 (5) | 0.188 (4) | 0.539 (3) | 0.104 (11)* | |
H3A | 0.287 (4) | 0.504 (3) | 0.993 (2) | 0.061 (8)* | |
H3B | 0.228 (4) | 0.514 (3) | 0.879 (2) | 0.058 (7)* | |
H4 | 0.291 (3) | 0.703 (3) | 0.3406 (19) | 0.045 (6)* | |
H4A | 0.079 (4) | 1.108 (3) | 1.312 (2) | 0.048 (6)* | |
H4B | −0.073 (4) | 0.975 (3) | 1.305 (2) | 0.054 (7)* | |
H4C | −0.095 (3) | 1.099 (3) | 1.2305 (19) | 0.047 (6)* | |
H6 | 0.258 (3) | 0.624 (2) | 0.6510 (17) | 0.034 (5)* | |
H9 | −0.034 (3) | 0.734 (2) | 0.9835 (18) | 0.040 (6)* | |
H10 | −0.175 (3) | 0.858 (2) | 1.1112 (18) | 0.045 (6)* | |
H12 | 0.358 (3) | 1.052 (2) | 1.2448 (19) | 0.043 (6)* | |
H13 | 0.491 (3) | 0.919 (2) | 1.1214 (19) | 0.046 (6)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0316 (2) | 0.0261 (2) | 0.0246 (2) | 0.00636 (15) | 0.00722 (15) | 0.00042 (14) |
O1 | 0.0594 (9) | 0.0210 (6) | 0.0322 (6) | 0.0025 (5) | 0.0048 (6) | −0.0031 (5) |
O2 | 0.0802 (11) | 0.0231 (6) | 0.0389 (7) | 0.0033 (6) | 0.0215 (7) | 0.0042 (5) |
O3 | 0.0857 (12) | 0.0359 (7) | 0.0298 (7) | −0.0001 (7) | 0.0165 (7) | 0.0007 (5) |
O4 | 0.0831 (11) | 0.0281 (7) | 0.0422 (8) | 0.0031 (7) | 0.0239 (7) | −0.0087 (6) |
O5 | 0.1223 (16) | 0.0238 (7) | 0.0453 (8) | 0.0059 (8) | 0.0049 (9) | 0.0087 (6) |
O6 | 0.1260 (17) | 0.0514 (9) | 0.0403 (8) | −0.0152 (10) | 0.0396 (10) | −0.0016 (7) |
O7 | 0.1023 (14) | 0.0469 (9) | 0.0338 (8) | −0.0208 (9) | 0.0125 (8) | −0.0127 (6) |
O8 | 0.0314 (7) | 0.0433 (7) | 0.0445 (7) | 0.0089 (5) | 0.0073 (5) | −0.0064 (6) |
O9 | 0.0519 (8) | 0.0417 (7) | 0.0281 (6) | 0.0155 (6) | 0.0111 (6) | 0.0079 (5) |
N1 | 0.0501 (9) | 0.0317 (7) | 0.0264 (7) | 0.0042 (7) | 0.0090 (6) | −0.0011 (6) |
N2 | 0.0451 (9) | 0.0215 (7) | 0.0365 (8) | 0.0043 (6) | 0.0084 (6) | −0.0002 (6) |
N3 | 0.0512 (10) | 0.0267 (7) | 0.0316 (8) | 0.0033 (7) | 0.0057 (7) | −0.0038 (6) |
N4 | 0.0358 (8) | 0.0262 (7) | 0.0247 (7) | 0.0052 (6) | 0.0074 (6) | −0.0019 (5) |
C1 | 0.0269 (8) | 0.0235 (7) | 0.0257 (7) | 0.0031 (6) | 0.0029 (6) | 0.0014 (6) |
C2 | 0.0270 (8) | 0.0221 (7) | 0.0277 (8) | 0.0031 (6) | 0.0023 (6) | −0.0016 (6) |
C3 | 0.0306 (8) | 0.0276 (8) | 0.0235 (7) | 0.0036 (6) | 0.0051 (6) | −0.0011 (6) |
C4 | 0.0329 (9) | 0.0243 (8) | 0.0278 (8) | 0.0039 (6) | 0.0057 (6) | 0.0037 (6) |
C5 | 0.0303 (8) | 0.0184 (7) | 0.0305 (8) | 0.0036 (6) | 0.0043 (6) | −0.0003 (6) |
C6 | 0.0299 (8) | 0.0242 (7) | 0.0252 (8) | 0.0039 (6) | 0.0041 (6) | −0.0018 (6) |
C7 | 0.0392 (9) | 0.0241 (7) | 0.0276 (8) | 0.0012 (6) | 0.0049 (7) | 0.0015 (6) |
C8 | 0.0314 (8) | 0.0229 (7) | 0.0240 (7) | 0.0036 (6) | 0.0071 (6) | −0.0012 (6) |
C9 | 0.0309 (9) | 0.0318 (8) | 0.0299 (8) | −0.0031 (7) | 0.0050 (7) | −0.0083 (7) |
C10 | 0.0253 (8) | 0.0356 (9) | 0.0325 (8) | −0.0009 (7) | 0.0065 (6) | −0.0047 (7) |
C11 | 0.0316 (8) | 0.0228 (7) | 0.0223 (7) | 0.0038 (6) | 0.0070 (6) | 0.0003 (6) |
C12 | 0.0314 (9) | 0.0359 (9) | 0.0348 (9) | −0.0024 (7) | 0.0024 (7) | −0.0134 (7) |
C13 | 0.0243 (8) | 0.0412 (10) | 0.0398 (10) | −0.0004 (7) | 0.0048 (7) | −0.0114 (8) |
S1—O8 | 1.4317 (14) | C1—C6 | 1.379 (2) |
S1—O9 | 1.4417 (13) | C1—C2 | 1.439 (2) |
S1—N3 | 1.6019 (17) | C1—C7 | 1.495 (2) |
S1—C8 | 1.7692 (16) | C2—C3 | 1.429 (2) |
O1—C2 | 1.2874 (19) | C3—C4 | 1.377 (2) |
O2—C7 | 1.315 (2) | C4—C5 | 1.381 (2) |
O2—H1 | 1.03 (4) | C4—H4 | 0.88 (2) |
O3—C7 | 1.209 (2) | C5—C6 | 1.391 (2) |
O4—N2 | 1.224 (2) | C6—H6 | 0.94 (2) |
O5—N2 | 1.221 (2) | C8—C9 | 1.383 (2) |
O6—N1 | 1.220 (2) | C8—C13 | 1.385 (2) |
O7—N1 | 1.207 (2) | C9—C10 | 1.381 (2) |
N1—C3 | 1.459 (2) | C9—H9 | 0.94 (2) |
N2—C5 | 1.454 (2) | C10—C11 | 1.384 (2) |
N3—H3A | 0.81 (3) | C10—H10 | 0.96 (2) |
N3—H3B | 0.84 (3) | C11—C12 | 1.373 (2) |
N4—C11 | 1.467 (2) | C12—C13 | 1.388 (2) |
N4—H4A | 0.91 (3) | C12—H12 | 0.93 (2) |
N4—H4B | 0.93 (3) | C13—H13 | 0.89 (2) |
N4—H4C | 0.89 (2) | ||
O8—S1—O9 | 117.22 (9) | C3—C4—C5 | 118.86 (15) |
O8—S1—N3 | 112.63 (9) | C3—C4—H4 | 122.1 (15) |
O9—S1—N3 | 106.50 (9) | C5—C4—H4 | 119.0 (15) |
O8—S1—C8 | 107.21 (8) | C4—C5—C6 | 121.74 (14) |
O9—S1—C8 | 108.05 (8) | C4—C5—N2 | 119.18 (15) |
N3—S1—C8 | 104.42 (8) | C6—C5—N2 | 119.05 (14) |
C7—O2—H1 | 107 (2) | C1—C6—C5 | 119.35 (15) |
O7—N1—O6 | 122.87 (16) | C1—C6—H6 | 120.5 (12) |
O7—N1—C3 | 119.31 (15) | C5—C6—H6 | 120.2 (12) |
O6—N1—C3 | 117.82 (15) | O3—C7—O2 | 121.66 (16) |
O5—N2—O4 | 123.38 (15) | O3—C7—C1 | 122.58 (15) |
O5—N2—C5 | 118.28 (15) | O2—C7—C1 | 115.73 (14) |
O4—N2—C5 | 118.35 (14) | C9—C8—C13 | 121.07 (15) |
S1—N3—H3A | 114 (2) | C9—C8—S1 | 119.84 (12) |
S1—N3—H3B | 113.0 (18) | C13—C8—S1 | 119.01 (13) |
H3A—N3—H3B | 118 (3) | C10—C9—C8 | 119.29 (15) |
C11—N4—H4A | 112.6 (16) | C10—C9—H9 | 120.6 (13) |
C11—N4—H4B | 107.8 (15) | C8—C9—H9 | 120.1 (13) |
H4A—N4—H4B | 113 (2) | C9—C10—C11 | 119.16 (16) |
C11—N4—H4C | 108.7 (15) | C9—C10—H10 | 120.2 (14) |
H4A—N4—H4C | 107 (2) | C11—C10—H10 | 120.6 (14) |
H4B—N4—H4C | 108 (2) | C12—C11—C10 | 122.13 (15) |
C6—C1—C2 | 121.91 (14) | C12—C11—N4 | 119.89 (15) |
C6—C1—C7 | 118.03 (14) | C10—C11—N4 | 117.97 (15) |
C2—C1—C7 | 120.02 (14) | C11—C12—C13 | 118.59 (16) |
O1—C2—C3 | 124.22 (15) | C11—C12—H12 | 120.9 (14) |
O1—C2—C1 | 120.62 (14) | C13—C12—H12 | 120.5 (14) |
C3—C2—C1 | 115.14 (13) | C8—C13—C12 | 119.74 (17) |
C4—C3—C2 | 122.99 (14) | C8—C13—H13 | 119.9 (15) |
C4—C3—N1 | 116.37 (14) | C12—C13—H13 | 120.3 (15) |
C2—C3—N1 | 120.64 (14) | ||
C6—C1—C2—O1 | 178.45 (15) | C4—C5—C6—C1 | −0.2 (3) |
C7—C1—C2—O1 | −3.9 (2) | N2—C5—C6—C1 | 177.72 (15) |
C6—C1—C2—C3 | 0.0 (2) | C6—C1—C7—O3 | 5.2 (3) |
C7—C1—C2—C3 | 177.62 (15) | C2—C1—C7—O3 | −172.54 (18) |
O1—C2—C3—C4 | −178.04 (16) | C6—C1—C7—O2 | −176.65 (16) |
C1—C2—C3—C4 | 0.3 (2) | C2—C1—C7—O2 | 5.6 (2) |
O1—C2—C3—N1 | 2.0 (3) | O8—S1—C8—C9 | −165.23 (14) |
C1—C2—C3—N1 | −179.58 (15) | O9—S1—C8—C9 | 67.57 (16) |
O7—N1—C3—C4 | −153.24 (19) | N3—S1—C8—C9 | −45.52 (16) |
O6—N1—C3—C4 | 26.3 (3) | O8—S1—C8—C13 | 17.90 (17) |
O7—N1—C3—C2 | 26.7 (3) | O9—S1—C8—C13 | −109.30 (15) |
O6—N1—C3—C2 | −153.79 (19) | N3—S1—C8—C13 | 137.61 (15) |
C2—C3—C4—C5 | −0.6 (3) | C13—C8—C9—C10 | −1.4 (3) |
N1—C3—C4—C5 | 179.33 (15) | S1—C8—C9—C10 | −178.22 (14) |
C3—C4—C5—C6 | 0.5 (3) | C8—C9—C10—C11 | 1.1 (3) |
C3—C4—C5—N2 | −177.38 (15) | C9—C10—C11—C12 | 0.3 (3) |
O5—N2—C5—C4 | 6.8 (3) | C9—C10—C11—N4 | −178.77 (15) |
O4—N2—C5—C4 | −173.40 (17) | C10—C11—C12—C13 | −1.3 (3) |
O5—N2—C5—C6 | −171.11 (18) | N4—C11—C12—C13 | 177.78 (17) |
O4—N2—C5—C6 | 8.7 (3) | C9—C8—C13—C12 | 0.4 (3) |
C2—C1—C6—C5 | −0.1 (2) | S1—C8—C13—C12 | 177.27 (15) |
C7—C1—C6—C5 | −177.75 (15) | C11—C12—C13—C8 | 0.9 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H1···O1 | 1.03 (4) | 1.48 (4) | 2.462 (2) | 157 (3) |
N3—H3A···O6i | 0.82 (3) | 2.53 (2) | 3.172 (2) | 137 (2) |
N3—H3A···O8ii | 0.82 (3) | 2.46 (3) | 3.090 (2) | 135 (2) |
N3—H3B···O3 | 0.84 (3) | 2.10 (3) | 2.934 (2) | 170 (3) |
N4—H4A···O1iii | 0.91 (3) | 1.93 (3) | 2.822 (2) | 166 (3) |
N4—H4A···O7iii | 0.91 (3) | 2.41 (3) | 2.870 (2) | 111.2 (19) |
N4—H4B···O2iv | 0.93 (3) | 2.01 (3) | 2.926 (2) | 172 (2) |
N4—H4B···O4v | 0.93 (3) | 2.51 (3) | 2.880 (2) | 104 (2) |
N4—H4C···O9v | 0.89 (2) | 1.97 (2) | 2.867 (2) | 176 (2) |
C4—H4···O5 | 0.88 (3) | 2.42 (3) | 2.711 (2) | 100.0 (18) |
C9—H9···O7vi | 0.94 (2) | 2.57 (2) | 3.414 (2) | 150.6 (16) |
C10—H10···O8vii | 0.96 (2) | 2.43 (2) | 3.171 (2) | 133.5 (16) |
C13—H13···O8 | 0.89 (2) | 2.53 (2) | 2.896 (2) | 105.3 (15) |
Symmetry codes: (i) x, y, z+1; (ii) −x+1, −y+1, −z+2; (iii) x, y+1, z+1; (iv) −x, −y+1, −z+2; (v) −x, −y+2, −z+2; (vi) −x, −y+1, −z+1; (vii) x−1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C7H3N2O7+·C6H9N2O2S− |
Mr | 400.33 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 7.0167 (9), 9.137 (1), 12.430 (1) |
α, β, γ (°) | 90.77 (1), 99.736 (9), 95.70 (1) |
V (Å3) | 781.17 (15) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.27 |
Crystal size (mm) | 0.35 × 0.25 × 0.20 |
Data collection | |
Diffractometer | Nonius CAD-4 diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3867, 3575, 3080 |
Rint | 0.010 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.037, 0.098, 1.05 |
No. of reflections | 3575 |
No. of parameters | 293 |
H-atom treatment | All H-atom parameters refined |
Δρmax, Δρmin (e Å−3) | 0.39, −0.35 |
Computer programs: CAD-4 Software (Enraf-Nonius, 1989), CAD-4 Software, PROCESS DATA (Gable et al., 1994), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON for Windows (Spek, 1999).
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H1···O1 | 1.03 (4) | 1.48 (4) | 2.462 (2) | 157 (3) |
N3—H3A···O6i | 0.82 (3) | 2.53 (2) | 3.172 (2) | 137 (2) |
N3—H3A···O8ii | 0.82 (3) | 2.46 (3) | 3.090 (2) | 135 (2) |
N3—H3B···O3 | 0.84 (3) | 2.10 (3) | 2.934 (2) | 170 (3) |
N4—H4A···O1iii | 0.91 (3) | 1.93 (3) | 2.822 (2) | 166 (3) |
N4—H4A···O7iii | 0.91 (3) | 2.41 (3) | 2.870 (2) | 111.2 (19) |
N4—H4B···O2iv | 0.93 (3) | 2.01 (3) | 2.926 (2) | 172 (2) |
N4—H4B···O4v | 0.93 (3) | 2.51 (3) | 2.880 (2) | 104 (2) |
N4—H4C···O9v | 0.89 (2) | 1.97 (2) | 2.867 (2) | 176 (2) |
C4—H4···O5 | 0.88 (3) | 2.42 (3) | 2.711 (2) | 100.0 (18) |
C9—H9···O7vi | 0.94 (2) | 2.57 (2) | 3.414 (2) | 150.6 (16) |
C10—H10···O8vii | 0.96 (2) | 2.43 (2) | 3.171 (2) | 133.5 (16) |
C13—H13···O8 | 0.89 (2) | 2.53 (2) | 2.896 (2) | 105.3 (15) |
Symmetry codes: (i) x, y, z+1; (ii) −x+1, −y+1, −z+2; (iii) x, y+1, z+1; (iv) −x, −y+1, −z+2; (v) −x, −y+2, −z+2; (vi) −x, −y+1, −z+1; (vii) x−1, y, z. |
3,5-Dinitrosalicylic acid (DNSA) provides one of the best chemical synthons for the construction of hydrogen-bonded structural motifs. The acid has provided examples of polymorphism in which associations with solvent molecules such as water (two examples), dioxane (four examples) and tert-butyl alcohol (one example) give a variety of hydrogen-bonded molecular assemblies (Smith et al., 1995; Kumar et al., 1999). The low pKa of the acid (2.18) also means that with Lewis bases, protonation of the hetero-N atom usually occurs, giving further promotion of hydrogen bonding. We have synthesized and determined the structures of the proton-transfer compounds with the isomeric aminobenzoic acids (Smith et al., 1995), viz. 3-amino-1H-1,2,4-triazole (Smith et al., 1996), 8-aminoquinoline (Smith, Wermuth, Bott et al., 2001), 8-hydroxyquinoline (Smith, Wermuth & White, 2001), guanidine (Smith, Bott & Wermuth, 2001a) and 8-quinolylurea (Smith, Bott & Wermuth, 2001b). All of these are 1:1 except for the 1:2 adduct with 4-aminobenzoic acid.
In a continuation of the study of the nature of the interactions of DNSA with Lewis bases, reaction with sulfanilamide (4-aminobenzenesulfonamide, ABSA), gave large yellow crystals of the title compound [(ABSA)+(DNSA)-], (I). The structure determination has shown that the amine group of sulfanilamide is protonated (Fig. 1), subsequently giving an extensively hydrogen-bonded network polymer in which all ABSA H atoms are involved in a total of eight associations [five to the protonated amine (two three-centred); three to the amide (one three-centred)], with DNSA oxygen acceptors or sulfonate O atoms of other ABSA molecules.
The sulfonilamide cation molecules form centrosymmetric hydrogen-bonded cyclic dimers through the sulfonamide groups [N4—H4C···O9 2.867 (2) Å: symmetry code: -x, 2 - y, 2 - z] (Fig. 2). These dimers are linked by weak hydrogen bonds [C10—H10···O8 3.171 (2) Å; symmetry code: 1 - x, y, z] to form infinite chains extending down the a axis of the cell. Hydrogen bonds between the protonated amine groups and sulfanilamide O atoms [N3—H3A···O8 3.090 (2) Å; symmetry code: 1 - x, 1 - y, 2 - z] form a two-dimensional network parallel to (001). The 3,5-dinitrosalicylate anion molecules are stacked down the a cell direction and are linked peripherally to the ABSA framework sheets by N—H···O hydrogen bonds (Table 1).
The usual intramolecular hydrogen bonding is found between the phenolic O atom and the anti-related H atom on the carboxyl group [O2—H1···O1 2.462 (2) Å], comparing closely with the mean for the current series (2.461 Å). This arrangement with the H atom located on the carboxyl O atom rather than the phenolic O atom is found in 75% of the known proton-transfer compounds of DNSA with Lewis bases (Smith, Bott, Wermuth, Healy et al., 2001).