Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804033112/sj6042sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804033112/sj6042Isup2.hkl |
CCDC reference: 263665
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (C-C) = 0.002 Å
- R factor = 0.041
- wR factor = 0.117
- Data-to-parameter ratio = 25.2
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT391_ALERT_3_B Deviating Methyl C14 H-C-H Bond Angle ...... 98.10 Deg.
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97 PLAT350_ALERT_3_C Short C-H Bond (0.96A) C14 - H14C ... 0.82 Ang. PLAT391_ALERT_3_C Deviating Methyl C7 H-C-H Bond Angle ...... 100.50 Deg. PLAT480_ALERT_4_C Long H...A H-Bond Reported H6 .. O2 .. 2.63 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H9 .. O1 .. 2.65 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H2 .. O1 .. 2.79 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H7A .. O3 .. 2.77 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H12 .. O1 .. 2.70 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H14C .. O1 .. 2.94 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H7B .. CG1 .. 3.10 Ang. PLAT481_ALERT_4_C Long D...A H-Bond Reported C7 .. CG1 .. 3.98 Ang.
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 11 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 ALERT type 3 Indicator that the structure quality may be low 8 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: COLLECT (Nonius, 2000); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPAK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.
C14H14O3S | F(000) = 552 |
Mr = 262.31 | Dx = 1.374 Mg m−3 |
Monoclinic, P21/c | Melting point: 327 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 7.8660 (4) Å | Cell parameters from 9865 reflections |
b = 20.0760 (9) Å | θ = 2.5–35.0° |
c = 8.1060 (3) Å | µ = 0.25 mm−1 |
β = 97.794 (2)° | T = 150 K |
V = 1268.26 (10) Å3 | Fragment, colorless |
Z = 4 | 0.50 × 0.35 × 0.35 mm |
Nonius KappaCCD (with an Oxford Cryosystems Cryostream cooler) diffractometer | 5524 independent reflections |
Radiation source: fine-focus sealed tube | 3367 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.032 |
ω scans with κ offsets | θmax = 34.9°, θmin = 2.6° |
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997) | h = 0→12 |
Tmin = 0.858, Tmax = 0.917 | k = −26→32 |
21364 measured reflections | l = −13→12 |
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)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.117 | All H-atom parameters refined |
S = 0.92 | w = 1/[σ2(Fo2) + (0.0644P)2] where P = (Fo2 + 2Fc2)/3 |
5524 reflections | (Δ/σ)max = 0.001 |
219 parameters | Δρmax = 0.41 e Å−3 |
0 restraints | Δρmin = −0.59 e Å−3 |
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. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.25996 (4) | 0.383759 (15) | 0.00752 (3) | 0.02754 (9) | |
O1 | 0.21136 (12) | 0.44225 (5) | −0.08727 (10) | 0.0340 (2) | |
O2 | 0.35778 (13) | 0.33301 (5) | −0.05904 (11) | 0.0402 (2) | |
O3 | 0.37859 (10) | 0.40493 (4) | 0.17657 (9) | 0.02781 (18) | |
C1 | 0.07902 (14) | 0.34927 (6) | 0.07832 (12) | 0.0242 (2) | |
C2 | −0.06203 (15) | 0.38947 (6) | 0.09062 (13) | 0.0250 (2) | |
C3 | −0.20214 (15) | 0.36281 (6) | 0.15409 (14) | 0.0265 (2) | |
C4 | −0.20357 (15) | 0.29625 (6) | 0.20499 (12) | 0.0256 (2) | |
C5 | −0.05973 (17) | 0.25704 (6) | 0.19050 (15) | 0.0294 (2) | |
C6 | 0.08153 (16) | 0.28281 (6) | 0.12752 (14) | 0.0290 (2) | |
C7 | −0.35724 (18) | 0.26793 (7) | 0.27191 (17) | 0.0337 (3) | |
C8 | 0.33171 (14) | 0.46136 (6) | 0.26614 (13) | 0.0245 (2) | |
C9 | 0.36483 (17) | 0.52367 (6) | 0.20666 (15) | 0.0321 (3) | |
C10 | 0.3262 (2) | 0.57912 (7) | 0.29501 (16) | 0.0399 (3) | |
C11 | 0.2568 (2) | 0.57124 (7) | 0.44199 (16) | 0.0406 (3) | |
C12 | 0.22894 (18) | 0.50841 (7) | 0.50132 (15) | 0.0366 (3) | |
C13 | 0.26575 (15) | 0.45098 (6) | 0.41504 (13) | 0.0276 (2) | |
C14 | 0.2385 (2) | 0.38298 (7) | 0.48339 (16) | 0.0375 (3) | |
H2 | −0.0624 (18) | 0.4333 (7) | 0.0566 (15) | 0.025 (3)* | |
H3 | −0.295 (2) | 0.3932 (8) | 0.1729 (18) | 0.044 (4)* | |
H5 | −0.068 (2) | 0.2122 (8) | 0.2180 (17) | 0.039 (4)* | |
H6 | 0.172 (3) | 0.2590 (9) | 0.116 (2) | 0.058 (5)* | |
H7A | −0.416 (2) | 0.3029 (10) | 0.321 (2) | 0.065 (5)* | |
H7B | −0.320 (2) | 0.2333 (8) | 0.352 (2) | 0.050 (4)* | |
H7C | −0.433 (3) | 0.2438 (9) | 0.195 (3) | 0.068 (6)* | |
H9 | 0.415 (2) | 0.5251 (8) | 0.101 (2) | 0.050 (5)* | |
H10 | 0.350 (2) | 0.6214 (8) | 0.2528 (18) | 0.043 (4)* | |
H11 | 0.232 (2) | 0.6111 (9) | 0.5038 (19) | 0.056 (5)* | |
H12 | 0.1833 (18) | 0.4999 (7) | 0.6092 (19) | 0.038 (4)* | |
H14A | 0.129 (3) | 0.3645 (9) | 0.437 (2) | 0.067 (6)* | |
H14B | 0.307 (2) | 0.3513 (9) | 0.447 (2) | 0.062 (6)* | |
H14C | 0.245 (3) | 0.3841 (9) | 0.585 (3) | 0.068 (6)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.02750 (15) | 0.03394 (17) | 0.02256 (13) | 0.00256 (12) | 0.00840 (10) | −0.00067 (10) |
O1 | 0.0370 (5) | 0.0411 (5) | 0.0250 (4) | 0.0000 (4) | 0.0077 (3) | 0.0078 (3) |
O2 | 0.0399 (5) | 0.0464 (6) | 0.0375 (5) | 0.0080 (5) | 0.0172 (4) | −0.0093 (4) |
O3 | 0.0233 (4) | 0.0313 (4) | 0.0290 (4) | 0.0033 (3) | 0.0045 (3) | 0.0000 (3) |
C1 | 0.0259 (5) | 0.0276 (6) | 0.0191 (4) | 0.0007 (4) | 0.0032 (4) | −0.0027 (4) |
C2 | 0.0265 (5) | 0.0234 (5) | 0.0251 (5) | 0.0017 (4) | 0.0027 (4) | 0.0024 (4) |
C3 | 0.0243 (5) | 0.0269 (6) | 0.0283 (5) | 0.0029 (5) | 0.0036 (4) | 0.0020 (4) |
C4 | 0.0276 (5) | 0.0272 (5) | 0.0213 (4) | −0.0019 (5) | 0.0009 (4) | −0.0003 (4) |
C5 | 0.0339 (6) | 0.0225 (6) | 0.0308 (5) | 0.0005 (5) | 0.0011 (4) | −0.0002 (4) |
C6 | 0.0284 (6) | 0.0267 (6) | 0.0317 (5) | 0.0069 (5) | 0.0037 (4) | −0.0035 (4) |
C7 | 0.0338 (7) | 0.0314 (7) | 0.0363 (6) | −0.0033 (6) | 0.0069 (5) | 0.0042 (5) |
C8 | 0.0204 (5) | 0.0277 (6) | 0.0250 (5) | 0.0013 (4) | 0.0013 (4) | 0.0012 (4) |
C9 | 0.0339 (6) | 0.0336 (7) | 0.0294 (6) | −0.0048 (5) | 0.0062 (5) | 0.0054 (5) |
C10 | 0.0518 (9) | 0.0289 (7) | 0.0370 (6) | −0.0036 (6) | −0.0008 (6) | 0.0044 (5) |
C11 | 0.0512 (9) | 0.0357 (7) | 0.0332 (6) | 0.0025 (6) | −0.0004 (5) | −0.0075 (5) |
C12 | 0.0422 (8) | 0.0437 (8) | 0.0241 (5) | −0.0037 (6) | 0.0046 (5) | −0.0058 (5) |
C13 | 0.0274 (6) | 0.0333 (6) | 0.0216 (5) | −0.0044 (5) | 0.0013 (4) | 0.0017 (4) |
C14 | 0.0509 (9) | 0.0373 (7) | 0.0244 (6) | −0.0105 (7) | 0.0058 (5) | 0.0029 (5) |
S1—O2 | 1.4261 (9) | C7—H7B | 0.969 (17) |
S1—O1 | 1.4268 (9) | C7—H7C | 0.94 (2) |
S1—O3 | 1.6070 (8) | C8—C9 | 1.3781 (16) |
S1—C1 | 1.7482 (12) | C8—C13 | 1.3926 (15) |
O3—C8 | 1.4210 (13) | C9—C10 | 1.3797 (19) |
C1—C2 | 1.3865 (16) | C9—H9 | 0.988 (17) |
C1—C6 | 1.3919 (17) | C10—C11 | 1.385 (2) |
C2—C3 | 1.3855 (16) | C10—H10 | 0.943 (16) |
C2—H2 | 0.922 (14) | C11—C12 | 1.378 (2) |
C3—C4 | 1.3991 (16) | C11—H11 | 0.978 (17) |
C3—H3 | 0.982 (16) | C12—C13 | 1.3990 (18) |
C4—C5 | 1.3962 (17) | C12—H12 | 1.004 (14) |
C4—C7 | 1.5021 (16) | C13—C14 | 1.4994 (18) |
C5—C6 | 1.3845 (17) | C14—H14A | 0.96 (2) |
C5—H5 | 0.933 (16) | C14—H14B | 0.905 (18) |
C6—H6 | 0.874 (19) | C14—H14C | 0.82 (2) |
C7—H7A | 0.96 (2) | ||
O2—S1—O1 | 120.20 (5) | C4—C7—H7C | 115.2 (12) |
O2—S1—O3 | 103.35 (5) | H7A—C7—H7C | 111.0 (16) |
O1—S1—O3 | 108.89 (5) | H7B—C7—H7C | 100.6 (15) |
O2—S1—C1 | 110.26 (6) | C9—C8—C13 | 123.33 (11) |
O1—S1—C1 | 109.40 (6) | C9—C8—O3 | 118.06 (10) |
O3—S1—C1 | 103.26 (5) | C13—C8—O3 | 118.46 (10) |
C8—O3—S1 | 119.06 (7) | C8—C9—C10 | 119.03 (12) |
C2—C1—C6 | 121.18 (11) | C8—C9—H9 | 116.4 (9) |
C2—C1—S1 | 119.21 (9) | C10—C9—H9 | 124.6 (9) |
C6—C1—S1 | 119.55 (9) | C9—C10—C11 | 119.65 (13) |
C3—C2—C1 | 119.11 (11) | C9—C10—H10 | 118.0 (9) |
C3—C2—H2 | 120.6 (9) | C11—C10—H10 | 122.4 (9) |
C1—C2—H2 | 120.3 (9) | C12—C11—C10 | 120.30 (13) |
C2—C3—C4 | 121.13 (11) | C12—C11—H11 | 121.1 (10) |
C2—C3—H3 | 117.8 (9) | C10—C11—H11 | 118.5 (10) |
C4—C3—H3 | 120.7 (9) | C11—C12—C13 | 121.77 (12) |
C5—C4—C3 | 118.33 (11) | C11—C12—H12 | 123.5 (8) |
C5—C4—C7 | 121.20 (11) | C13—C12—H12 | 114.7 (8) |
C3—C4—C7 | 120.46 (11) | C8—C13—C12 | 115.89 (11) |
C6—C5—C4 | 121.37 (11) | C8—C13—C14 | 123.03 (11) |
C6—C5—H5 | 122.2 (10) | C12—C13—C14 | 121.07 (11) |
C4—C5—H5 | 116.3 (10) | C13—C14—H14A | 111.8 (12) |
C5—C6—C1 | 118.87 (11) | C13—C14—H14B | 113.5 (11) |
C5—C6—H6 | 122.8 (12) | H14A—C14—H14B | 97.9 (15) |
C1—C6—H6 | 118.4 (12) | C13—C14—H14C | 110.7 (13) |
C4—C7—H7A | 109.4 (11) | H14A—C14—H14C | 109.6 (18) |
C4—C7—H7B | 109.1 (11) | H14B—C14—H14C | 112.7 (17) |
H7A—C7—H7B | 111.4 (15) | ||
O2—S1—O3—C8 | 171.63 (8) | C4—C5—C6—C1 | 0.14 (17) |
O1—S1—O3—C8 | 42.75 (9) | C2—C1—C6—C5 | −0.34 (17) |
C1—S1—O3—C8 | −73.44 (8) | S1—C1—C6—C5 | 177.06 (9) |
O2—S1—C1—C2 | −156.72 (9) | S1—O3—C8—C9 | −77.18 (12) |
O1—S1—C1—C2 | −22.41 (10) | S1—O3—C8—C13 | 107.14 (10) |
O3—S1—C1—C2 | 93.41 (9) | C13—C8—C9—C10 | −2.19 (19) |
O2—S1—C1—C6 | 25.82 (11) | O3—C8—C9—C10 | −177.64 (11) |
O1—S1—C1—C6 | 160.13 (9) | C8—C9—C10—C11 | 0.7 (2) |
O3—S1—C1—C6 | −84.04 (9) | C9—C10—C11—C12 | 1.0 (2) |
C6—C1—C2—C3 | 0.40 (16) | C10—C11—C12—C13 | −1.3 (2) |
S1—C1—C2—C3 | −177.01 (8) | C9—C8—C13—C12 | 1.87 (18) |
C1—C2—C3—C4 | −0.26 (16) | O3—C8—C13—C12 | 177.30 (10) |
C2—C3—C4—C5 | 0.06 (16) | C9—C8—C13—C14 | −176.74 (12) |
C2—C3—C4—C7 | −179.38 (11) | O3—C8—C13—C14 | −1.31 (17) |
C3—C4—C5—C6 | 0.00 (17) | C11—C12—C13—C8 | −0.08 (19) |
C7—C4—C5—C6 | 179.43 (11) | C11—C12—C13—C14 | 178.56 (13) |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···O1 | 0.922 (14) | 2.591 (13) | 2.9441 (14) | 103.4 (10) |
C6—H6···O2 | 0.874 (19) | 2.631 (18) | 2.9859 (16) | 105.5 (13) |
C9—H9···O1 | 0.988 (17) | 2.647 (16) | 3.0043 (16) | 101.5 (11) |
C14—H14A···Cg1 | 0.96 (2) | 2.780 | 3.597 | 143 |
C14—H14B···O3 | 0.905 (18) | 2.575 (18) | 2.8873 (16) | 101.0 (13) |
C2—H2···O1i | 0.922 (14) | 2.785 (15) | 3.5757 (15) | 144.5 (10) |
C3—H3···O3ii | 0.982 (16) | 2.579 (16) | 3.4333 (14) | 145.5 (12) |
C7—H7A···O3ii | 0.96 (2) | 2.77 (2) | 3.4705 (17) | 130.6 (14) |
C12—H12···O1iii | 1.004 (14) | 2.701 (15) | 3.6097 (15) | 150.6 (11) |
C14—H14C···O1iii | 0.82 (2) | 2.94 (2) | 3.7115 (16) | 156.5 (16) |
C7—H7B···Cg1iv | 0.97 (2) | 3.100 | 3.977 | 151 |
Symmetry codes: (i) −x, −y+1, −z; (ii) x−1, y, z; (iii) x, y, z+1; (iv) x, −y−1/2, z−1/2. |
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