The cation, anion and water molecules of the title compound, C7H11N2O3S+·Cl-·2H2O are linked by hydrogen bonds into a three-dimensional network. The cation and anion lie on mirror planes, and both are disordered.
Supporting information
CCDC reference: 269418
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.003 Å
- R factor = 0.039
- wR factor = 0.130
- Data-to-parameter ratio = 11.1
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT165_ALERT_3_C Nr. of Status R Flagged Non-Hydrogen Atoms ..... 1
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for S1'
PLAT301_ALERT_3_C Main Residue Disorder ......................... 25.00 Perc.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 5
PLAT751_ALERT_4_C Bond Calc 1.45806, Rep 1.459(2) ...... Senseless su
N1 -C3 1.555 1.555
PLAT751_ALERT_4_C Bond Calc 1.37780, Rep 1.3780(10) ...... Senseless su
C2 -C3 1.555 1.555
PLAT751_ALERT_4_C Bond Calc 1.39383, Rep 1.394(2) ...... Senseless su
C3 -C4 1.555 1.555
PLAT751_ALERT_4_C Bond Calc 1.39383, Rep 1.394(2) ...... Senseless su
C4 -C3 1.555 7.575
PLAT752_ALERT_4_C Angle Calc 118.69, Rep 118.70(10) ...... Senseless su
C3 -C2 -C1 1.555 1.555 1.555
PLAT752_ALERT_4_C Angle Calc 123.32, Rep 123.40(10) ...... Senseless su
C2 -C3 -C4 1.555 1.555 1.555
PLAT752_ALERT_4_C Angle Calc 117.82, Rep 117.80(10) ...... Senseless su
C2 -C3 -N1 1.555 1.555 1.555
PLAT752_ALERT_4_C Angle Calc 118.86, Rep 118.80(10) ...... Senseless su
C4 -C3 -N1 1.555 1.555 1.555
PLAT752_ALERT_4_C Angle Calc 122.26, Rep 122.30(10) ...... Senseless su
C3 -C4 -C5 1.555 1.555 1.555
PLAT752_ALERT_4_C Angle Calc 108.25, Rep 108(2) ...... Senseless su
C3 -N1 -H1N1 1.555 1.555 1.555
PLAT752_ALERT_4_C Angle Calc 111.77, Rep 112(2) ...... Senseless su
C3 -N1 -H1N2 1.555 1.555 1.555
PLAT752_ALERT_4_C Angle Calc 108.84, Rep 109(2) ...... Senseless su
C3 -N1 -H1N3 1.555 1.555 1.555
PLAT753_ALERT_4_C Torsion Calc 1.44, Rep 1.5(2) ...... Senseless su
C2 -C1 -C2 -C3 7.575 1.555 1.555 1.555
PLAT753_ALERT_4_C Torsion Calc 0.82, Rep 0.80(10) ...... Senseless su
C1 -C2 -C3 -C4 1.555 1.555 1.555 1.555
PLAT753_ALERT_4_C Torsion Calc -178.79, Rep -178.8(2) ...... Senseless su
C1 -C2 -C3 -N1 1.555 1.555 1.555 1.555
PLAT753_ALERT_4_C Torsion Calc -2.88, Rep -2.9(2) ...... Senseless su
C2 -C3 -C4 -C3 1.555 1.555 1.555 7.575
PLAT753_ALERT_4_C Torsion Calc 176.73, Rep 176.70(10) ...... Senseless su
N1 -C3 -C4 -C3 1.555 1.555 1.555 7.575
PLAT753_ALERT_4_C Torsion Calc 176.47, Rep 176.50(10) ...... Senseless su
C2 -C3 -C4 -C5 1.555 1.555 1.555 1.555
PLAT753_ALERT_4_C Torsion Calc -3.92, Rep -3.9(2) ...... Senseless su
N1 -C3 -C4 -C5 1.555 1.555 1.555 1.555
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
24 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
1 ALERT type 2 Indicator that the structure model may be wrong or deficient
2 ALERT type 3 Indicator that the structure quality may be low
20 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
2,6-Diammonio-4-toluenesulfonate chloride dihydrate
top
Crystal data top
C7H11N2O3S+·Cl−·2H2O | F(000) = 576 |
Mr = 274.72 | Dx = 1.583 Mg m−3 |
Orthorhombic, Pnma | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2n | Cell parameters from 9848 reflections |
a = 9.196 (2) Å | θ = 3.1–27.5° |
b = 9.407 (2) Å | µ = 0.52 mm−1 |
c = 13.322 (3) Å | T = 295 K |
V = 1152.4 (4) Å3 | Block, pale pink |
Z = 4 | 0.36 × 0.26 × 0.20 mm |
Data collection top
Rigaki R-AXIS-RAPID IP diffractometer | 1393 independent reflections |
Radiation source: fine-focus sealed tube | 1286 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.017 |
ω scans | θmax = 27.5°, θmin = 3.1° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −10→11 |
Tmin = 0.798, Tmax = 0.903 | k = −12→12 |
10743 measured reflections | l = −17→17 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.130 | H-atom parameters constrained |
S = 1.11 | w = 1/[σ2(Fo2) + (0.0844P)2 + 0.4374P] where P = (Fo2 + 2Fc2)/3 |
1393 reflections | (Δ/σ)max = 0.001 |
125 parameters | Δρmax = 0.48 e Å−3 |
40 restraints | Δρmin = −0.31 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
Cl1 | 0.601 (1) | 0.7500 | −0.0293 (3) | 0.050 (1) | 0.78 (3) |
Cl1' | 0.546 (3) | 0.7500 | −0.016 (1) | 0.047 (2) | 0.22 (3) |
S1 | 0.5924 (2) | 0.7500 | 0.62908 (9) | 0.0235 (3) | 0.744 (5) |
O1 | 0.7257 (3) | 0.7500 | 0.6869 (2) | 0.0355 (7) | 0.744 (5) |
O2 | 0.5128 (3) | 0.6184 (3) | 0.6437 (2) | 0.0461 (8) | 0.744 (5) |
S1' | 0.5357 (6) | 0.7500 | 0.6113 (3) | 0.0326 (9) | 0.256 (5) |
O1' | 0.3836 (7) | 0.7500 | 0.5850 (6) | 0.042 (2) | 0.256 (5) |
O2' | 0.569 (2) | 0.619 (1) | 0.659 (1) | 0.088 (4) | 0.256 (5) |
O1w | 0.5780 (2) | 0.5091 (2) | 0.1404 (1) | 0.0402 (4) | |
N1 | 0.7661 (2) | 0.4891 (1) | 0.3094 (1) | 0.0286 (3) | |
C1 | 0.6469 (2) | 0.7500 | 0.5006 (2) | 0.0233 (4) | |
C2 | 0.6765 (1) | 0.6219 (1) | 0.4530 (1) | 0.0237 (3) | |
C3 | 0.7386 (1) | 0.6247 (1) | 0.3589 (1) | 0.0223 (3) | |
C4 | 0.7752 (2) | 0.7500 | 0.3091 (2) | 0.0220 (4) | |
C5 | 0.8509 (3) | 0.7500 | 0.2085 (2) | 0.0316 (5) | |
H1w1 | 0.583 (3) | 0.574 (2) | 0.096 (2) | 0.069 (9)* | |
H1w2 | 0.568 (3) | 0.429 (1) | 0.111 (2) | 0.059 (8)* | |
H1n1 | 0.741 (2) | 0.423 (2) | 0.349 (2) | 0.077 (9)* | |
H1n2 | 0.855 (1) | 0.480 (3) | 0.293 (2) | 0.049 (7)* | |
H1n3 | 0.713 (2) | 0.484 (3) | 0.256 (1) | 0.072 (9)* | |
H2 | 0.6548 | 0.5359 | 0.4840 | 0.028* | |
H5a | 0.7888 | 0.7068 | 0.1592 | 0.047* | 0.50 |
H5b | 0.9399 | 0.6971 | 0.2133 | 0.047* | 0.50 |
H5c | 0.8720 | 0.8460 | 0.1890 | 0.047* | 0.50 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.080 (4) | 0.0368 (6) | 0.0330 (7) | 0.000 | 0.001 (1) | 0.000 |
Cl1' | 0.048 (6) | 0.053 (3) | 0.040 (3) | 0.000 | 0.005 (3) | 0.000 |
S1 | 0.0318 (7) | 0.0211 (4) | 0.0178 (5) | 0.000 | 0.0044 (4) | 0.000 |
O1 | 0.050 (1) | 0.034 (1) | 0.023 (1) | 0.000 | −0.008 (1) | 0.000 |
O2 | 0.059 (2) | 0.046 (1) | 0.034 (1) | −0.028 (1) | 0.015 (1) | −0.005 (1) |
S1' | 0.032 (2) | 0.048 (2) | 0.018 (1) | 0.000 | 0.003 (1) | 0.000 |
O1' | 0.039 (4) | 0.049 (4) | 0.037 (4) | 0.000 | 0.008 (3) | 0.000 |
O2' | 0.109 (8) | 0.093 (7) | 0.062 (6) | 0.048 (6) | 0.033 (5) | 0.051 (5) |
O1w | 0.046 (1) | 0.039 (1) | 0.036 (1) | 0.003 (1) | −0.004 (1) | 0.001 (1) |
N1 | 0.033 (1) | 0.022 (1) | 0.031 (1) | −0.0002 (5) | 0.0050 (5) | −0.0058 (5) |
C1 | 0.026 (1) | 0.025 (1) | 0.019 (1) | 0.000 | 0.002 (1) | 0.000 |
C2 | 0.028 (1) | 0.021 (1) | 0.023 (1) | −0.002 (1) | 0.001 (1) | 0.002 (1) |
C3 | 0.023 (1) | 0.020 (1) | 0.024 (1) | 0.000 (1) | −0.001 (1) | −0.004 (1) |
C4 | 0.021 (1) | 0.025 (1) | 0.021 (1) | 0.000 | 0.001 (1) | 0.000 |
C5 | 0.035 (1) | 0.031 (1) | 0.028 (1) | 0.000 | 0.011 (1) | 0.000 |
Geometric parameters (Å, º) top
S1—O1 | 1.447 (3) | C3—C4 | 1.394 (2) |
S1—O2 | 1.451 (2) | C4—C3i | 1.394 (2) |
S1—O2i | 1.451 (2) | C4—C5 | 1.511 (3) |
S1—C1 | 1.783 (2) | O1w—H1w1 | 0.85 (1) |
S1'—O1' | 1.442 (7) | O1w—H1w2 | 0.85 (1) |
S1'—O2' | 1.421 (7) | N1—H1n1 | 0.85 (1) |
S1'—O2'i | 1.421 (7) | N1—H1n2 | 0.85 (1) |
S1'—C1 | 1.795 (4) | N1—H1n3 | 0.86 (1) |
N1—C3 | 1.459 (2) | C2—H2 | 0.93 |
C1—C2 | 1.389 (1) | C5—H5a | 0.96 |
C1—C2i | 1.389 (1) | C5—H5b | 0.96 |
C2—C3 | 1.378 (1) | C5—H5c | 0.96 |
| | | |
O1—S1—O2 | 110.9 (2) | C4—C3—N1 | 118.8 (1) |
O1—S1—O2i | 110.9 (2) | C3—C4—C3i | 115.5 (2) |
O2—S1—O2i | 117.0 (3) | C3—C4—C5 | 122.3 (1) |
O1—S1—C1 | 105.8 (1) | C3i—C4—C5 | 122.3 (1) |
O2—S1—C1 | 105.7 (1) | H1w1—O1w—H1w2 | 109 (2) |
O2i—S1—C1 | 105.7 (1) | C3—N1—H1n1 | 108 (2) |
O2'i—S1'—O2' | 121 (2) | C3—N1—H1n2 | 112 (2) |
O2'i—S1'—O1' | 108.4 (8) | H1n1—N1—H1n2 | 110 (2) |
O2'—S1'—O1' | 108.4 (8) | C3—N1—H1n3 | 109 (2) |
O2'i—S1'—C1 | 103.9 (6) | H1n1—N1—H1n3 | 109 (2) |
O2'—S1'—C1 | 103.9 (6) | H1n2—N1—H1n3 | 109 (2) |
O1'—S1'—C1 | 110.7 (4) | C3—C2—H2 | 120.7 |
C2—C1—C2i | 120.4 (2) | C1—C2—H2 | 120.7 |
C2—C1—S1 | 119.6 (1) | C4—C5—H5a | 109.5 |
C2i—C1—S1 | 119.6 (1) | C4—C5—H5b | 109.5 |
C2—C1—S1' | 119.1 (1) | H5a—C5—H5b | 109.5 |
C2i—C1—S1' | 119.1 (1) | C4—C5—H5c | 109.5 |
C3—C2—C1 | 118.7 (1) | H5a—C5—H5c | 109.5 |
C2—C3—C4 | 123.4 (1) | H5b—C5—H5c | 109.5 |
C2—C3—N1 | 117.8 (1) | | |
| | | |
O1—S1—C1—C2 | 86.1 (1) | O1'—S1'—C1—C2i | 83.45 (17) |
O2—S1—C1—C2 | −31.6 (3) | C2i—C1—C2—C3 | 1.5 (2) |
O2i—S1—C1—C2 | −156.3 (2) | S1—C1—C2—C3 | −170.6 (1) |
O1—S1—C1—C2i | −86.1 (1) | S1'—C1—C2—C3 | 168.2 (2) |
O2—S1—C1—C2i | 156.3 (2) | C1—C2—C3—C4 | 0.8 (1) |
O2i—S1—C1—C2i | 31.6 (3) | C1—C2—C3—N1 | −178.8 (2) |
O2'i—S1'—C1—C2 | 160.4 (8) | C2—C3—C4—C3i | −2.9 (2) |
O2'—S1'—C1—C2 | 33 (1) | N1—C3—C4—C3i | 176.7 (1) |
O1'—S1'—C1—C2 | −83.5 (2) | C2—C3—C4—C5 | 176.5 (1) |
O2'i—S1'—C1—C2i | −33 (1) | N1—C3—C4—C5 | −3.9 (2) |
O2'—S1'—C1—C2i | −160.4 (8) | | |
Symmetry code: (i) x, −y+3/2, z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1n3···O1ii | 0.86 (1) | 2.45 (3) | 2.780 (2) | 103 (2) |
N1—H1n1···O2iii | 0.85 (1) | 2.37 (2) | 2.827 (3) | 114 (2) |
N1—H1n2···O1wiv | 0.85 (1) | 2.25 (2) | 2.952 (2) | 140 (2) |
N1—H1n3···O1w | 0.86 (1) | 2.00 (1) | 2.845 (2) | 169 (3) |
N1—H1n1···O1′iii | 0.85 (1) | 2.18 (1) | 2.989 (5) | 160 (2) |
N1—H1n2···O2′ii | 0.85 (1) | 2.14 (2) | 2.71 (1) | 125 (2) |
O1w—H1w1···Cl1 | 0.85 (1) | 2.36 (1) | 3.207 (4) | 179 (3) |
O1w—H1w2···Cl1v | 0.85 (1) | 2.54 (2) | 3.291 (5) | 148 (2) |
O1w—H1w1···Cl1′ | 0.85 (1) | 2.26 (1) | 3.094 (9) | 168 (3) |
O1w—H1w2···Cl1′v | 0.85 (1) | 2.35 (2) | 3.158 (5) | 158 (2) |
Symmetry codes: (ii) −x+3/2, −y+1, z−1/2; (iii) −x+1, −y+1, −z+1; (iv) x+1/2, y, −z+1/2; (v) −x+1, −y+1, −z. |