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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805003922/cv6455sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805003922/cv6455Isup2.hkl
Contains datablock I

CCDC reference: 269418

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.039
  • wR factor = 0.130
  • Data-to-parameter ratio = 11.1

checkCIF/PLATON results

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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

Computing details top

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·2H2OF(000) = 576
Mr = 274.72Dx = 1.583 Mg m3
Orthorhombic, PnmaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2nCell parameters from 9848 reflections
a = 9.196 (2) Åθ = 3.1–27.5°
b = 9.407 (2) ŵ = 0.52 mm1
c = 13.322 (3) ÅT = 295 K
V = 1152.4 (4) Å3Block, pale pink
Z = 40.36 × 0.26 × 0.20 mm
Data collection top
Rigaki R-AXIS-RAPID IP
diffractometer
1393 independent reflections
Radiation source: fine-focus sealed tube1286 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.017
ω scansθmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 1011
Tmin = 0.798, Tmax = 0.903k = 1212
10743 measured reflectionsl = 1717
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.130H-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 parametersΔρmax = 0.48 e Å3
40 restraintsΔρmin = 0.31 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Cl10.601 (1)0.75000.0293 (3)0.050 (1)0.78 (3)
Cl1'0.546 (3)0.75000.016 (1)0.047 (2)0.22 (3)
S10.5924 (2)0.75000.62908 (9)0.0235 (3)0.744 (5)
O10.7257 (3)0.75000.6869 (2)0.0355 (7)0.744 (5)
O20.5128 (3)0.6184 (3)0.6437 (2)0.0461 (8)0.744 (5)
S1'0.5357 (6)0.75000.6113 (3)0.0326 (9)0.256 (5)
O1'0.3836 (7)0.75000.5850 (6)0.042 (2)0.256 (5)
O2'0.569 (2)0.619 (1)0.659 (1)0.088 (4)0.256 (5)
O1w0.5780 (2)0.5091 (2)0.1404 (1)0.0402 (4)
N10.7661 (2)0.4891 (1)0.3094 (1)0.0286 (3)
C10.6469 (2)0.75000.5006 (2)0.0233 (4)
C20.6765 (1)0.6219 (1)0.4530 (1)0.0237 (3)
C30.7386 (1)0.6247 (1)0.3589 (1)0.0223 (3)
C40.7752 (2)0.75000.3091 (2)0.0220 (4)
C50.8509 (3)0.75000.2085 (2)0.0316 (5)
H1w10.583 (3)0.574 (2)0.096 (2)0.069 (9)*
H1w20.568 (3)0.429 (1)0.111 (2)0.059 (8)*
H1n10.741 (2)0.423 (2)0.349 (2)0.077 (9)*
H1n20.855 (1)0.480 (3)0.293 (2)0.049 (7)*
H1n30.713 (2)0.484 (3)0.256 (1)0.072 (9)*
H20.65480.53590.48400.028*
H5a0.78880.70680.15920.047*0.50
H5b0.93990.69710.21330.047*0.50
H5c0.87200.84600.18900.047*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.080 (4)0.0368 (6)0.0330 (7)0.0000.001 (1)0.000
Cl1'0.048 (6)0.053 (3)0.040 (3)0.0000.005 (3)0.000
S10.0318 (7)0.0211 (4)0.0178 (5)0.0000.0044 (4)0.000
O10.050 (1)0.034 (1)0.023 (1)0.0000.008 (1)0.000
O20.059 (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)0.0000.003 (1)0.000
O1'0.039 (4)0.049 (4)0.037 (4)0.0000.008 (3)0.000
O2'0.109 (8)0.093 (7)0.062 (6)0.048 (6)0.033 (5)0.051 (5)
O1w0.046 (1)0.039 (1)0.036 (1)0.003 (1)0.004 (1)0.001 (1)
N10.033 (1)0.022 (1)0.031 (1)0.0002 (5)0.0050 (5)0.0058 (5)
C10.026 (1)0.025 (1)0.019 (1)0.0000.002 (1)0.000
C20.028 (1)0.021 (1)0.023 (1)0.002 (1)0.001 (1)0.002 (1)
C30.023 (1)0.020 (1)0.024 (1)0.000 (1)0.001 (1)0.004 (1)
C40.021 (1)0.025 (1)0.021 (1)0.0000.001 (1)0.000
C50.035 (1)0.031 (1)0.028 (1)0.0000.011 (1)0.000
Geometric parameters (Å, º) top
S1—O11.447 (3)C3—C41.394 (2)
S1—O21.451 (2)C4—C3i1.394 (2)
S1—O2i1.451 (2)C4—C51.511 (3)
S1—C11.783 (2)O1w—H1w10.85 (1)
S1'—O1'1.442 (7)O1w—H1w20.85 (1)
S1'—O2'1.421 (7)N1—H1n10.85 (1)
S1'—O2'i1.421 (7)N1—H1n20.85 (1)
S1'—C11.795 (4)N1—H1n30.86 (1)
N1—C31.459 (2)C2—H20.93
C1—C21.389 (1)C5—H5a0.96
C1—C2i1.389 (1)C5—H5b0.96
C2—C31.378 (1)C5—H5c0.96
O1—S1—O2110.9 (2)C4—C3—N1118.8 (1)
O1—S1—O2i110.9 (2)C3—C4—C3i115.5 (2)
O2—S1—O2i117.0 (3)C3—C4—C5122.3 (1)
O1—S1—C1105.8 (1)C3i—C4—C5122.3 (1)
O2—S1—C1105.7 (1)H1w1—O1w—H1w2109 (2)
O2i—S1—C1105.7 (1)C3—N1—H1n1108 (2)
O2'i—S1'—O2'121 (2)C3—N1—H1n2112 (2)
O2'i—S1'—O1'108.4 (8)H1n1—N1—H1n2110 (2)
O2'—S1'—O1'108.4 (8)C3—N1—H1n3109 (2)
O2'i—S1'—C1103.9 (6)H1n1—N1—H1n3109 (2)
O2'—S1'—C1103.9 (6)H1n2—N1—H1n3109 (2)
O1'—S1'—C1110.7 (4)C3—C2—H2120.7
C2—C1—C2i120.4 (2)C1—C2—H2120.7
C2—C1—S1119.6 (1)C4—C5—H5a109.5
C2i—C1—S1119.6 (1)C4—C5—H5b109.5
C2—C1—S1'119.1 (1)H5a—C5—H5b109.5
C2i—C1—S1'119.1 (1)C4—C5—H5c109.5
C3—C2—C1118.7 (1)H5a—C5—H5c109.5
C2—C3—C4123.4 (1)H5b—C5—H5c109.5
C2—C3—N1117.8 (1)
O1—S1—C1—C286.1 (1)O1'—S1'—C1—C2i83.45 (17)
O2—S1—C1—C231.6 (3)C2i—C1—C2—C31.5 (2)
O2i—S1—C1—C2156.3 (2)S1—C1—C2—C3170.6 (1)
O1—S1—C1—C2i86.1 (1)S1'—C1—C2—C3168.2 (2)
O2—S1—C1—C2i156.3 (2)C1—C2—C3—C40.8 (1)
O2i—S1—C1—C2i31.6 (3)C1—C2—C3—N1178.8 (2)
O2'i—S1'—C1—C2160.4 (8)C2—C3—C4—C3i2.9 (2)
O2'—S1'—C1—C233 (1)N1—C3—C4—C3i176.7 (1)
O1'—S1'—C1—C283.5 (2)C2—C3—C4—C5176.5 (1)
O2'i—S1'—C1—C2i33 (1)N1—C3—C4—C53.9 (2)
O2'—S1'—C1—C2i160.4 (8)
Symmetry code: (i) x, y+3/2, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1n3···O1ii0.86 (1)2.45 (3)2.780 (2)103 (2)
N1—H1n1···O2iii0.85 (1)2.37 (2)2.827 (3)114 (2)
N1—H1n2···O1wiv0.85 (1)2.25 (2)2.952 (2)140 (2)
N1—H1n3···O1w0.86 (1)2.00 (1)2.845 (2)169 (3)
N1—H1n1···O1iii0.85 (1)2.18 (1)2.989 (5)160 (2)
N1—H1n2···O2ii0.85 (1)2.14 (2)2.71 (1)125 (2)
O1w—H1w1···Cl10.85 (1)2.36 (1)3.207 (4)179 (3)
O1w—H1w2···Cl1v0.85 (1)2.54 (2)3.291 (5)148 (2)
O1w—H1w1···Cl10.85 (1)2.26 (1)3.094 (9)168 (3)
O1w—H1w2···Cl1v0.85 (1)2.35 (2)3.158 (5)158 (2)
Symmetry codes: (ii) x+3/2, y+1, z1/2; (iii) x+1, y+1, z+1; (iv) x+1/2, y, z+1/2; (v) x+1, y+1, z.
 

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