Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807011129/wk2042sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807011129/wk2042Isup2.hkl |
CCDC reference: 643130
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.003 Å
- R factor = 0.040
- wR factor = 0.098
- Data-to-parameter ratio = 18.3
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT431_ALERT_2_B Short Inter HL..A Contact Cl1 .. S1 .. 3.11 Ang.
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 1 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 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Data collection: SMART-W2K/NT (Bruker, 2003); cell refinement: SAINT-W2K/NT (Bruker, 2003); data reduction: SAINT-W2K/NT; program(s) used to solve structure: SHELXTL-NT (Bruker, 2003); program(s) used to refine structure: SHELXTL-NT; molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXTL-NT.
C4H6NOS+·Cl−·H2O | F(000) = 352 |
Mr = 169.62 | Dx = 1.541 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 1395 reflections |
a = 6.0291 (6) Å | θ = 2.8–26.3° |
b = 8.2420 (8) Å | µ = 0.74 mm−1 |
c = 14.7222 (14) Å | T = 173 K |
β = 91.921 (2)° | Block, colorless |
V = 731.16 (12) Å3 | 0.24 × 0.21 × 0.18 mm |
Z = 4 |
Bruker SMART APEX CCD area-detector diffractometer | 1743 independent reflections |
Radiation source: fine-focus sealed tube | 1477 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.034 |
Detector resolution: 8.366 pixels mm-1 | θmax = 27.9°, θmin = 2.8° |
ω scans | h = −7→7 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −10→7 |
Tmin = 0.843, Tmax = 0.879 | l = −19→19 |
5225 measured reflections |
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)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.098 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0514P)2 + 0.0524P] where P = (Fo2 + 2Fc2)/3 |
1743 reflections | (Δ/σ)max < 0.001 |
95 parameters | Δρmax = 0.42 e Å−3 |
0 restraints | Δρmin = −0.28 e Å−3 |
Geometry. Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) 3.1318 (0.0043) x + 6.3397 (0.0050) y - 5.7326 (0.0107) z = 1.9214 (0.0074) * 0.0040 (0.0009) S1 * -0.0078 (0.0010) N1 * 0.0085 (0.0012) C1 * -0.0046 (0.0013) C2 * -0.0001 (0.0012) C3 0.0200 (0.0028) O1 0.0912 (0.0033) C4 Rms deviation of fitted atoms = 0.0058 |
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 | ||
Cl1 | 0.36295 (9) | 0.96320 (6) | 0.33374 (3) | 0.02883 (17) | |
S1 | −0.22387 (9) | 0.74074 (6) | 0.36102 (3) | 0.02494 (17) | |
O1 | 0.2917 (2) | 0.60650 (18) | 0.49143 (11) | 0.0290 (4) | |
N1 | 0.0167 (3) | 0.6416 (2) | 0.38481 (11) | 0.0218 (4) | |
C1 | 0.1044 (3) | 0.6750 (2) | 0.46684 (13) | 0.0219 (4) | |
C4 | 0.1257 (4) | 0.5417 (3) | 0.31670 (15) | 0.0295 (5) | |
H4A | 0.2528 | 0.6009 | 0.2934 | 0.044* | |
H4B | 0.0199 | 0.5177 | 0.2665 | 0.044* | |
H4C | 0.1770 | 0.4401 | 0.3448 | 0.044* | |
C3 | −0.2110 (4) | 0.8279 (3) | 0.46519 (14) | 0.0270 (5) | |
H3 | −0.3202 | 0.9009 | 0.4860 | 0.032* | |
C2 | −0.0300 (4) | 0.7835 (2) | 0.51574 (15) | 0.0260 (5) | |
H2 | 0.0029 | 0.8200 | 0.5759 | 0.031* | |
O2 | 0.4002 (4) | 0.7069 (2) | 0.64756 (12) | 0.0421 (5) | |
H2B | 0.396 (5) | 0.655 (4) | 0.693 (2) | 0.058 (10)* | |
H1 | 0.331 (5) | 0.636 (4) | 0.544 (2) | 0.060 (10)* | |
H2A | 0.467 (6) | 0.783 (4) | 0.656 (2) | 0.068 (12)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0311 (3) | 0.0292 (3) | 0.0262 (3) | 0.0001 (2) | 0.0008 (2) | −0.0015 (2) |
S1 | 0.0232 (3) | 0.0287 (3) | 0.0229 (3) | 0.0009 (2) | 0.0002 (2) | 0.00017 (19) |
O1 | 0.0274 (8) | 0.0321 (9) | 0.0271 (9) | 0.0014 (7) | −0.0048 (7) | −0.0002 (6) |
N1 | 0.0220 (8) | 0.0236 (9) | 0.0199 (9) | 0.0004 (7) | 0.0024 (7) | 0.0002 (6) |
C1 | 0.0232 (10) | 0.0212 (10) | 0.0213 (10) | −0.0050 (8) | 0.0002 (8) | 0.0035 (8) |
C4 | 0.0296 (11) | 0.0332 (12) | 0.0261 (11) | 0.0033 (9) | 0.0049 (9) | −0.0061 (9) |
C3 | 0.0300 (11) | 0.0254 (11) | 0.0257 (11) | 0.0000 (9) | 0.0044 (8) | −0.0025 (8) |
C2 | 0.0306 (11) | 0.0245 (11) | 0.0231 (11) | −0.0033 (9) | 0.0013 (8) | −0.0016 (8) |
O2 | 0.0634 (13) | 0.0362 (11) | 0.0260 (10) | −0.0142 (9) | −0.0103 (8) | 0.0035 (8) |
S1—N1 | 1.6911 (17) | C4—H4B | 0.9800 |
S1—C3 | 1.693 (2) | C4—H4C | 0.9800 |
O1—C1 | 1.303 (2) | C3—C2 | 1.351 (3) |
O1—H1 | 0.84 (3) | C3—H3 | 0.9500 |
N1—C1 | 1.331 (2) | C2—H2 | 0.9500 |
N1—C4 | 1.469 (3) | O2—H2B | 0.79 (3) |
C1—C2 | 1.419 (3) | O2—H2A | 0.75 (3) |
C4—H4A | 0.9800 | ||
N1—S1—C3 | 90.26 (9) | N1—C4—H4C | 109.5 |
C1—O1—H1 | 110 (2) | H4A—C4—H4C | 109.5 |
C1—N1—C4 | 124.18 (17) | H4B—C4—H4C | 109.5 |
C1—N1—S1 | 113.58 (14) | C2—C3—S1 | 113.30 (17) |
C4—N1—S1 | 121.97 (14) | C2—C3—H3 | 123.3 |
O1—C1—N1 | 118.49 (18) | S1—C3—H3 | 123.3 |
O1—C1—C2 | 129.52 (19) | C3—C2—C1 | 110.85 (19) |
N1—C1—C2 | 111.99 (18) | C3—C2—H2 | 124.6 |
N1—C4—H4A | 109.5 | C1—C2—H2 | 124.6 |
N1—C4—H4B | 109.5 | H2B—O2—H2A | 110 (4) |
H4A—C4—H4B | 109.5 | ||
C3—S1—N1—C1 | −1.08 (16) | S1—N1—C1—C2 | 1.6 (2) |
C3—S1—N1—C4 | −175.33 (17) | N1—S1—C3—C2 | 0.26 (17) |
C4—N1—C1—O1 | −5.0 (3) | S1—C3—C2—C1 | 0.6 (2) |
S1—N1—C1—O1 | −179.06 (14) | O1—C1—C2—C3 | 179.4 (2) |
C4—N1—C1—C2 | 175.70 (17) | N1—C1—C2—C3 | −1.4 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2A···Cl1i | 0.75 (3) | 2.33 (3) | 3.080 (2) | 171 (4) |
O2—H2B···Cl1ii | 0.79 (3) | 2.31 (3) | 3.093 (2) | 172 (3) |
O1—H1···O2 | 0.84 (3) | 1.67 (3) | 2.509 (2) | 176 (3) |
Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) x, −y+3/2, z+1/2. |