The title compound, [NO2C6H4SO2NHCH2CHOHCH2NH3]+[p-NO2C6H4SO3]- or C9H14N3O5S+·C6H4NO5S-, was isolated from the reaction between 1,3-diamino-2-hydroxypropane and p-nitrobenzenesulfonyl chloride in CH2Cl2. The fairly extensive hydrogen-bond system involving all `active' H atoms links the ions in the crystal into layers normal to the b axis.
Supporting information
CCDC reference: 198327
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.009 Å
- R factor = 0.053
- wR factor = 0.052
- Data-to-parameter ratio = 7.1
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Alert Level B:
REFNR_01 Alert B Ratio of reflections to parameters is < 8 for a
centrosymmetric structure
sine(theta)/lambda 0.6497
Proportion of unique data used 0.4303
Ratio reflections to parameters 7.1143
0 Alert Level A = Potentially serious problem
1 Alert Level B = Potential problem
0 Alert Level C = Please check
1,3-Diamino-2-hydroxypropane (0.2 g) was stirred with p-nitrobenzenesulfonyl chloride (0.5 g) and pyridine in dry CH2Cl2 (10 ml) under N2 at room temperature for 5 h. The reaction mixture was extracted with 5% aqueous HCl solution. The organic phase was dried and purified by silica chromatography [elution with CH2Cl2–MeOH in 50:1 (v:v)]. The pale-yellow monosulfonylated diamine was obtained in 75% yield. X-Ray quality crystals were obtained by slow evaporation of a 10 ml mixture of CH2Cl2 and MeOH in a 3:1 (v:v) ratio at room temperature over a few days.
The positions of the H atoms were generated geometrically (C—H and N—H bond lengths fixed at 0.95 Å) with assigned isotropic displacement parameters and were allowed to ride on their respective parent C and N atoms before the final cycle of least-squares refinement.
Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT-Plus (Bruker, 1999); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: TEXSAN (Molecular Structure Corporation, 1992); software used to prepare material for publication: TEXSAN.
Crystal data top
C9H14N3O5S+·C6H4NO5S− | F(000) = 992.00 |
Mr = 478.45 | Dx = 1.576 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.7107 Å |
a = 6.7120 (8) Å | Cell parameters from 46 reflections |
b = 31.392 (1) Å | θ = 2.5–14° |
c = 9.8260 (9) Å | µ = 0.33 mm−1 |
β = 103.170 (5)° | T = 298 K |
V = 2015.9 (3) Å3 | Block, colourless |
Z = 4 | 0.23 × 0.20 × 0.11 mm |
Data collection top
Bruker SMART CCD Area detector diffractometer | 1992 reflections with I > 2σ(I) |
Radiation source: X-ray tube | Rint = 0.049 |
Graphite monochromator | θmax = 27.5°, θmin = 2.5° |
ϕ and ω scans | h = −8→5 |
12619 measured reflections | k = −38→40 |
4629 independent reflections | l = −8→12 |
Refinement top
Refinement on F | 0 restraints |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.053 | w = 1/[(σ)2(Fo) + (p/2)2(Fo)2] where P = 0.041 |
wR(F2) = 0.052 | (Δ/σ)max < 0.001 |
S = 1.19 | Δρmax = 0.40 e Å−3 |
1992 reflections | Δρmin = −0.28 e Å−3 |
280 parameters | |
Crystal data top
C9H14N3O5S+·C6H4NO5S− | V = 2015.9 (3) Å3 |
Mr = 478.45 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 6.7120 (8) Å | µ = 0.33 mm−1 |
b = 31.392 (1) Å | T = 298 K |
c = 9.8260 (9) Å | 0.23 × 0.20 × 0.11 mm |
β = 103.170 (5)° | |
Data collection top
Bruker SMART CCD Area detector diffractometer | 1992 reflections with I > 2σ(I) |
12619 measured reflections | Rint = 0.049 |
4629 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.053 | 0 restraints |
wR(F2) = 0.052 | H-atom parameters constrained |
S = 1.19 | Δρmax = 0.40 e Å−3 |
1992 reflections | Δρmin = −0.28 e Å−3 |
280 parameters | |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
S1 | 0.3248 (2) | 0.14269 (4) | 0.5080 (2) | 0.0522 (5) | |
S2 | 0.2987 (2) | 0.19924 (4) | 0.9308 (1) | 0.0450 (4) | |
O1 | 0.2129 (8) | −0.0668 (1) | 0.4951 (6) | 0.101 (2) | |
O2 | 0.3339 (9) | −0.0590 (1) | 0.7171 (6) | 0.109 (2) | |
O3 | 0.3156 (6) | 0.1473 (1) | 0.3628 (4) | 0.075 (1) | |
O4 | 0.4979 (5) | 0.1584 (1) | 0.6097 (4) | 0.071 (1) | |
O5 | −0.1228 (5) | 0.23851 (10) | 0.5015 (3) | 0.051 (1) | |
O6 | −0.3082 (7) | 0.0366 (1) | 0.9817 (5) | 0.106 (2) | |
O7 | −0.0373 (7) | 0.0160 (1) | 1.1292 (4) | 0.076 (2) | |
O8 | 0.1889 (6) | 0.2138 (1) | 0.7940 (3) | 0.059 (1) | |
O9 | 0.5115 (5) | 0.1895 (1) | 0.9395 (4) | 0.057 (1) | |
O10 | 0.2715 (5) | 0.2280 (1) | 1.0419 (3) | 0.052 (1) | |
N1 | 0.2738 (8) | −0.0449 (2) | 0.6001 (8) | 0.072 (2) | |
N2 | 0.1280 (7) | 0.1637 (1) | 0.5458 (4) | 0.052 (1) | |
N3 | −0.3619 (6) | 0.2535 (1) | 0.2239 (4) | 0.050 (1) | |
N4 | −0.1302 (9) | 0.0412 (2) | 1.0427 (6) | 0.068 (2) | |
C1 | 0.2834 (8) | 0.0019 (2) | 0.5782 (7) | 0.052 (2) | |
C2 | 0.2327 (8) | 0.0172 (2) | 0.4450 (6) | 0.054 (2) | |
C3 | 0.2454 (8) | 0.0607 (2) | 0.4242 (5) | 0.050 (2) | |
C4 | 0.3078 (7) | 0.0874 (2) | 0.5371 (5) | 0.042 (2) | |
C5 | 0.3552 (8) | 0.0706 (2) | 0.6710 (6) | 0.058 (2) | |
C6 | 0.3437 (9) | 0.0275 (2) | 0.6914 (6) | 0.062 (2) | |
C7 | −0.0727 (9) | 0.1644 (2) | 0.4501 (6) | 0.058 (2) | |
C8 | −0.1186 (8) | 0.2094 (2) | 0.3896 (6) | 0.057 (2) | |
C9 | −0.3160 (9) | 0.2109 (2) | 0.2878 (6) | 0.063 (2) | |
C10 | −0.0215 (9) | 0.0792 (2) | 1.0112 (6) | 0.053 (2) | |
C11 | −0.1330 (10) | 0.1126 (2) | 0.9460 (9) | 0.107 (3) | |
C12 | −0.0305 (10) | 0.1489 (2) | 0.9222 (8) | 0.099 (3) | |
C13 | 0.1789 (8) | 0.1510 (1) | 0.9604 (5) | 0.044 (2) | |
C14 | 0.2867 (8) | 0.1168 (2) | 1.0249 (5) | 0.050 (2) | |
C15 | 0.1885 (9) | 0.0801 (2) | 1.0494 (5) | 0.051 (2) | |
H2 | 0.1896 | −0.0016 | 0.3680 | 0.0649 | |
H2a | 0.1423 | 0.1764 | 0.6352 | 0.0628 | |
H3 | 0.2110 | 0.0721 | 0.3322 | 0.0597 | |
H3a1 | −0.4915 | 0.2530 | 0.1599 | 0.0596 | |
H3a2 | −0.2594 | 0.2611 | 0.1757 | 0.0596 | |
H3a3 | −0.3643 | 0.2739 | 0.2950 | 0.0596 | |
H5 | 0.3959 | 0.0890 | 0.7491 | 0.0695 | |
H5a | 0.0371 | 0.2505 | 0.5355 | 0.0779 | |
H6 | 0.3773 | 0.0158 | 0.7830 | 0.0741 | |
H7a | −0.1739 | 0.1565 | 0.4989 | 0.0699 | |
H7b | −0.0744 | 0.1449 | 0.3760 | 0.0699 | |
H8 | −0.0134 | 0.2177 | 0.3448 | 0.0683 | |
H9b | −0.4211 | 0.2034 | 0.3339 | 0.0758 | |
H9a | −0.3134 | 0.1909 | 0.2158 | 0.0758 | |
H11 | −0.2779 | 0.1109 | 0.9175 | 0.1279 | |
H12 | −0.1059 | 0.1728 | 0.8789 | 0.1193 | |
H14 | 0.4316 | 0.1185 | 1.0533 | 0.0598 | |
H15 | 0.2638 | 0.0560 | 1.0916 | 0.0610 | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0535 (9) | 0.0436 (8) | 0.063 (1) | −0.0084 (7) | 0.0207 (8) | −0.0065 (7) |
S2 | 0.0486 (9) | 0.0407 (7) | 0.0441 (8) | 0.0016 (7) | 0.0075 (6) | −0.0005 (7) |
O1 | 0.093 (4) | 0.053 (3) | 0.159 (5) | 0.000 (3) | 0.035 (4) | −0.002 (3) |
O2 | 0.131 (5) | 0.082 (3) | 0.128 (4) | 0.035 (3) | 0.058 (4) | 0.043 (3) |
O3 | 0.110 (4) | 0.059 (3) | 0.067 (3) | −0.012 (2) | 0.045 (2) | 0.002 (2) |
O4 | 0.048 (2) | 0.059 (2) | 0.104 (3) | −0.017 (2) | 0.010 (2) | −0.026 (2) |
O5 | 0.050 (2) | 0.044 (2) | 0.054 (2) | 0.001 (2) | 0.002 (2) | −0.006 (2) |
O6 | 0.074 (4) | 0.101 (4) | 0.131 (4) | −0.043 (3) | 0.002 (3) | 0.010 (3) |
O7 | 0.096 (4) | 0.068 (3) | 0.067 (3) | −0.015 (3) | 0.024 (3) | 0.008 (2) |
O8 | 0.083 (3) | 0.053 (2) | 0.037 (2) | 0.010 (2) | 0.006 (2) | 0.002 (2) |
O9 | 0.045 (2) | 0.058 (2) | 0.070 (3) | 0.001 (2) | 0.018 (2) | 0.009 (2) |
O10 | 0.056 (2) | 0.051 (2) | 0.047 (2) | 0.004 (2) | 0.004 (2) | −0.011 (2) |
N1 | 0.052 (4) | 0.056 (4) | 0.118 (6) | 0.015 (3) | 0.040 (4) | 0.008 (4) |
N2 | 0.052 (3) | 0.046 (2) | 0.055 (3) | 0.007 (2) | 0.004 (2) | −0.009 (2) |
N3 | 0.050 (3) | 0.051 (3) | 0.042 (3) | 0.002 (2) | −0.002 (2) | 0.005 (2) |
N4 | 0.066 (4) | 0.067 (4) | 0.073 (4) | −0.019 (3) | 0.020 (3) | −0.004 (3) |
C1 | 0.037 (3) | 0.047 (3) | 0.078 (4) | 0.005 (3) | 0.023 (3) | 0.004 (3) |
C2 | 0.042 (3) | 0.049 (3) | 0.070 (4) | −0.002 (3) | 0.010 (3) | −0.014 (3) |
C3 | 0.049 (4) | 0.051 (3) | 0.052 (3) | 0.002 (3) | 0.015 (3) | 0.001 (3) |
C4 | 0.037 (3) | 0.045 (3) | 0.046 (3) | 0.001 (2) | 0.016 (3) | −0.002 (3) |
C5 | 0.059 (4) | 0.066 (4) | 0.050 (4) | −0.004 (3) | 0.014 (3) | −0.007 (3) |
C6 | 0.064 (4) | 0.069 (4) | 0.056 (4) | 0.004 (3) | 0.021 (3) | 0.011 (3) |
C7 | 0.060 (4) | 0.039 (3) | 0.067 (4) | 0.004 (3) | −0.004 (3) | 0.000 (3) |
C8 | 0.057 (4) | 0.039 (3) | 0.065 (4) | 0.000 (3) | −0.005 (3) | −0.006 (3) |
C9 | 0.068 (4) | 0.050 (3) | 0.060 (4) | 0.000 (3) | −0.009 (3) | 0.001 (3) |
C10 | 0.053 (4) | 0.047 (3) | 0.062 (4) | −0.009 (3) | 0.016 (3) | 0.002 (3) |
C11 | 0.044 (4) | 0.071 (5) | 0.194 (8) | −0.014 (4) | 0.005 (5) | 0.028 (5) |
C12 | 0.049 (4) | 0.062 (4) | 0.174 (7) | 0.012 (3) | −0.002 (4) | 0.035 (5) |
C13 | 0.042 (3) | 0.039 (3) | 0.049 (3) | 0.003 (2) | 0.007 (3) | −0.003 (2) |
C14 | 0.041 (3) | 0.053 (3) | 0.054 (3) | 0.002 (3) | 0.008 (3) | 0.003 (3) |
C15 | 0.056 (4) | 0.049 (3) | 0.045 (3) | 0.004 (3) | 0.007 (3) | 0.005 (3) |
Geometric parameters (Å, º) top
S1—O3 | 1.421 (4) | C10—C11 | 1.360 (8) |
S1—O4 | 1.436 (4) | C10—C15 | 1.374 (7) |
S1—N2 | 1.594 (4) | C11—C12 | 1.378 (8) |
S1—C4 | 1.767 (5) | C12—C13 | 1.371 (7) |
S2—O8 | 1.452 (3) | C13—C14 | 1.365 (6) |
S2—O9 | 1.444 (3) | C14—C15 | 1.376 (7) |
S2—O10 | 1.459 (3) | O5—H5a | 1.11 |
S2—C13 | 1.770 (5) | N3—H3a1 | 0.95 |
O1—N1 | 1.230 (7) | N3—H3a3 | 0.95 |
O2—N1 | 1.212 (6) | C3—H3 | 0.95 |
O5—C8 | 1.434 (6) | C6—H6 | 0.95 |
O6—N4 | 1.217 (6) | C7—H7b | 0.95 |
O7—N4 | 1.222 (6) | C9—H9b | 0.95 |
N1—C1 | 1.488 (7) | C11—H11 | 0.95 |
N2—C7 | 1.457 (6) | C14—H14 | 0.95 |
N3—C9 | 1.481 (6) | N2—H2a | 0.95 |
N4—C10 | 1.468 (7) | N3—H3a2 | 0.95 |
C1—C2 | 1.362 (7) | C2—H2 | 0.95 |
C1—C6 | 1.357 (7) | C5—H5 | 0.95 |
C2—C3 | 1.387 (7) | C7—H7a | 0.95 |
C3—C4 | 1.378 (6) | C8—H8 | 0.95 |
C4—C5 | 1.385 (7) | C9—H9a | 0.95 |
C5—C6 | 1.374 (7) | C12—H12 | 0.95 |
C7—C8 | 1.535 (7) | C15—H15 | 0.95 |
C8—C9 | 1.468 (7) | | |
| | | |
O3—S1—O4 | 120.4 (2) | C12—C13—C14 | 119.4 (5) |
O3—S1—N2 | 110.0 (2) | C13—C14—C15 | 121.0 (5) |
O3—S1—C4 | 105.9 (2) | C10—C15—C14 | 118.1 (5) |
O4—S1—N2 | 106.1 (2) | C8—O5—H5a | 105.0 |
O4—S1—C4 | 107.3 (2) | C7—N2—H2a | 118.3 |
N2—S1—C4 | 106.3 (2) | C9—N3—H3a2 | 109.5 |
O8—S2—O9 | 114.0 (2) | H3a1—N3—H3a2 | 109.5 |
O8—S2—O10 | 112.0 (2) | H3a2—N3—H3a3 | 109.5 |
O8—S2—C13 | 105.5 (2) | C3—C2—H2 | 120.7 |
O9—S2—O10 | 112.2 (2) | C4—C3—H3 | 120.0 |
O9—S2—C13 | 106.8 (2) | C6—C5—H5 | 119.8 |
O10—S2—C13 | 105.5 (2) | C5—C6—H6 | 120.7 |
O1—N1—O2 | 124.5 (6) | N2—C7—H7b | 109.4 |
O1—N1—C1 | 116.6 (6) | C8—C7—H7b | 109.4 |
O2—N1—C1 | 118.9 (6) | O5—C8—H8 | 109.1 |
S1—N2—C7 | 123.3 (4) | C9—C8—H8 | 109.1 |
O6—N4—O7 | 123.6 (5) | N3—C9—H9a | 108.7 |
O6—N4—C10 | 118.1 (6) | C8—C9—H9a | 108.7 |
O7—N4—C10 | 118.2 (5) | C10—C11—H11 | 120.8 |
N1—C1—C2 | 118.5 (6) | C11—C12—H12 | 119.6 |
N1—C1—C6 | 118.7 (6) | C13—C14—H14 | 119.5 |
C2—C1—C6 | 122.8 (5) | C10—C15—H15 | 120.9 |
C1—C2—C3 | 118.6 (5) | S1—N2—H2a | 118.3 |
C2—C3—C4 | 119.9 (5) | C9—N3—H3a1 | 109.5 |
S1—C4—C3 | 119.1 (4) | C9—N3—H3a3 | 109.5 |
S1—C4—C5 | 121.2 (4) | H3a1—N3—H3a3 | 109.5 |
C3—C4—C5 | 119.7 (5) | C1—C2—H2 | 120.7 |
C4—C5—C6 | 120.4 (5) | C2—C3—H3 | 120.0 |
C1—C6—C5 | 118.7 (5) | C4—C5—H5 | 119.8 |
N2—C7—C8 | 109.8 (4) | C1—C6—H6 | 120.7 |
O5—C8—C7 | 109.0 (4) | N2—C7—H7a | 109.4 |
O5—C8—C9 | 109.3 (4) | C8—C7—H7a | 109.4 |
C7—C8—C9 | 111.3 (4) | H7a—C7—H7b | 109.5 |
N3—C9—C8 | 112.7 (4) | C7—C8—H8 | 109.1 |
N4—C10—C11 | 118.6 (6) | N3—C9—H9b | 108.7 |
N4—C10—C15 | 119.2 (5) | C8—C9—H9b | 108.7 |
C11—C10—C15 | 122.2 (5) | H9b—C9—H9a | 109.5 |
C10—C11—C12 | 118.3 (6) | C12—C11—H11 | 120.8 |
C11—C12—C13 | 120.9 (6) | C13—C12—H12 | 119.6 |
S2—C13—C12 | 118.1 (4) | C15—C14—H14 | 119.5 |
S2—C13—C14 | 122.4 (4) | C14—C15—H15 | 120.9 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2a···O8 | 0.95 | 1.92 | 2.852 (5) | 166 |
N3—H3a1···O10i | 0.95 | 1.91 | 2.809 (5) | 157 |
N3—H3a2···O5ii | 0.95 | 2.12 | 3.002 (5) | 154 |
N3—H3a3···O5 | 0.95 | 2.55 | 2.871 (5) | 100 |
N3—H3a3···O9iii | 0.95 | 2.14 | 3.038 (5) | 158 |
O5—H5a···O10ii | 1.11 | 1.70 | 2.791 (5) | 165 |
Symmetry codes: (i) x−1, y, z−1; (ii) x, −y+1/2, z−1/2; (iii) x−1, −y+1/2, z−1/2. |
Experimental details
Crystal data |
Chemical formula | C9H14N3O5S+·C6H4NO5S− |
Mr | 478.45 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 298 |
a, b, c (Å) | 6.7120 (8), 31.392 (1), 9.8260 (9) |
β (°) | 103.170 (5) |
V (Å3) | 2015.9 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.33 |
Crystal size (mm) | 0.23 × 0.20 × 0.11 |
|
Data collection |
Diffractometer | Bruker SMART CCD Area detector diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12619, 4629, 1992 |
Rint | 0.049 |
(sin θ/λ)max (Å−1) | 0.650 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.053, 0.052, 1.19 |
No. of reflections | 1992 |
No. of parameters | 280 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.40, −0.28 |
Selected geometric parameters (Å, º) topS1—O3 | 1.421 (4) | S2—C13 | 1.770 (5) |
S1—O4 | 1.436 (4) | O5—C8 | 1.434 (6) |
S1—N2 | 1.594 (4) | N2—C7 | 1.457 (6) |
S1—C4 | 1.767 (5) | N3—C9 | 1.481 (6) |
S2—O8 | 1.452 (3) | C7—C8 | 1.535 (7) |
S2—O9 | 1.444 (3) | C8—C9 | 1.468 (7) |
S2—O10 | 1.459 (3) | | |
| | | |
O3—S1—O4 | 120.4 (2) | S1—C4—C3 | 119.1 (4) |
O3—S1—N2 | 110.0 (2) | S1—C4—C5 | 121.2 (4) |
O3—S1—C4 | 105.9 (2) | N2—C7—C8 | 109.8 (4) |
O4—S1—N2 | 106.1 (2) | O5—C8—C7 | 109.0 (4) |
O4—S1—C4 | 107.3 (2) | O5—C8—C9 | 109.3 (4) |
N2—S1—C4 | 106.3 (2) | C7—C8—C9 | 111.3 (4) |
S1—N2—C7 | 123.3 (4) | N3—C9—C8 | 112.7 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2a···O8 | 0.95 | 1.92 | 2.852 (5) | 166 |
N3—H3a1···O10i | 0.95 | 1.91 | 2.809 (5) | 157 |
N3—H3a2···O5ii | 0.95 | 2.12 | 3.002 (5) | 154 |
N3—H3a3···O5 | 0.95 | 2.55 | 2.871 (5) | 100 |
N3—H3a3···O9iii | 0.95 | 2.14 | 3.038 (5) | 158 |
O5—H5a···O10ii | 1.11 | 1.70 | 2.791 (5) | 165 |
Symmetry codes: (i) x−1, y, z−1; (ii) x, −y+1/2, z−1/2; (iii) x−1, −y+1/2, z−1/2. |
Nitrobenzenesulfonamide is an efficient protecting reagent for preparing amine derivatives (Fukuyama et al., 1995; Hidai et al., 1999). Under controlled reaction conditions, mono-protected primary diamine was synthesized selectively and in high yield. The crystal of the title compound, (I), has an ionic structure, built of 2-hydroxy-3-(p-nitrobenzenesulfonylamino)propylammonium cations, [NO2C6H4SO2NHCH2CHOHCH2NH3]+, and p-nitrobenzenesulfonate anions, [p-NO2C6H4SO3]−, as shown in Fig. 1. The present X-ray diffraction study proved the successful formation of mono-substituted products and provided the first reported crystal structure with cationic mono protected diamine.
The S—O and S—N bond lengths in the cation, and the S—O and S—C bond lengths in the anion are comparable to those in the similar previously reported molecular fragments (Barrans & Cotrait, 1976; Brunzelle et al., 1999; Cook et al., 1971; Curtis & Pavkovic, 1983; Russell et al., 1994; Takahashi et al., 1998).
There are five `active' H atoms in the structure of (I), all of which participate in hydrogen bonds of the N—H···O═S, N—H···O(H) and O—H···O═S types (Table 2). The N—H···O═S and N—H···O(H) bonds are in the range 2.809 (5)–3.038 (5) Å. O5—H5a···O10 is a fairly strong interaction, with an O···O distance of 2.791 (5) Å and an O—H···O angle of 164.85 (18)°, which is typical for `anionic' O—H···O− hydrogen bonds in the crystal structures of salts (Jeffrey, 1997). These hydrogen bonds link cations and anions into the infinite two-dimensional aggregates, i.e. layers parallel to the [010] plane (Fig. 2).