Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680500276X/fl6137sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680500276X/fl6137Isup2.hkl |
CCDC reference: 269554
Key indicators
- Single-crystal X-ray study
- T = 120 K
- Mean (C-C) = 0.002 Å
- R factor = 0.036
- wR factor = 0.092
- Data-to-parameter ratio = 17.0
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT480_ALERT_4_B Long H...A H-Bond Reported H12 .. O2 .. 2.99 Ang.
Alert level C CRYSC01_ALERT_1_C The word below has not been recognised as a standard identifier. tan CRYSC01_ALERT_1_C No recognised colour has been given for crystal colour. PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.04 Ratio PLAT480_ALERT_4_C Long H...A H-Bond Reported H2 .. O2 .. 2.67 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H3 .. O2 .. 2.97 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H6 .. O1 .. 2.62 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H7A .. O2 .. 2.69 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H9 .. O3 .. 2.87 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H3 .. CG3 .. 2.83 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H5 .. CG3 .. 2.86 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H6 .. CG2 .. 3.01 Ang. PLAT481_ALERT_4_C Long D...A H-Bond Reported C3 .. O2 .. 3.80 Ang. PLAT482_ALERT_4_C Small D-H..A Angle Rep for C2 .. O2 .. 99.00 Deg.
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 13 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 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 1 ALERT type 3 Indicator that the structure quality may be low 11 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: COLLECT (Nonius, 1997); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1990); software used to prepare material for publication: SHELXL97.
C17H14O3S | Z = 2 |
Mr = 298.34 | F(000) = 312 |
Triclinic, P1 | Dx = 1.372 Mg m−3 |
Hall symbol: -P 1 | Melting point = 396–397 K |
a = 8.8693 (10) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.3982 (10) Å | Cell parameters from 3629 reflections |
c = 9.7112 (10) Å | θ = 2.5–30.0° |
α = 70.446 (4)° | µ = 0.23 mm−1 |
β = 71.335 (4)° | T = 120 K |
γ = 81.831 (8)° | Fragment, tan |
V = 722.12 (14) Å3 | 0.40 × 0.27 × 0.08 mm |
KappaCCD (with an Oxford Cryosystems Cryostream coller) diffractometer | 4173 independent reflections |
Radiation source: fine-focus sealed tube | 3618 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.017 |
ω scans with κ offsets | θmax = 30.1°, θmin = 3.1° |
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997) | h = −12→12 |
Tmin = 0.934, Tmax = 0.982 | k = −13→13 |
12785 measured reflections | l = −13→13 |
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)] = 0.036 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.092 | All H-atom parameters refined |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0371P)2 + 0.2951P] where P = (Fo2 + 2Fc2)/3 |
4173 reflections | (Δ/σ)max < 0.001 |
246 parameters | Δρmax = 0.36 e Å−3 |
0 restraints | Δρmin = −0.43 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 | 0.27616 (3) | 0.69621 (3) | 0.84693 (3) | 0.01878 (8) | |
O1 | 0.44043 (11) | 0.64780 (11) | 0.81136 (11) | 0.0262 (2) | |
O2 | 0.21933 (12) | 0.81989 (10) | 0.74096 (10) | 0.0278 (2) | |
O3 | 0.17074 (10) | 0.55929 (9) | 0.87136 (10) | 0.01995 (18) | |
C1 | 0.21628 (14) | 0.72478 (13) | 1.02625 (13) | 0.0169 (2) | |
C2 | 0.07282 (14) | 0.80386 (13) | 1.06793 (14) | 0.0191 (2) | |
C3 | 0.02221 (15) | 0.82293 (15) | 1.21147 (15) | 0.0226 (2) | |
C4 | 0.11336 (16) | 0.76464 (15) | 1.31332 (14) | 0.0238 (3) | |
C5 | 0.25789 (16) | 0.68812 (15) | 1.26721 (14) | 0.0236 (2) | |
C6 | 0.31085 (15) | 0.66675 (14) | 1.12429 (14) | 0.0207 (2) | |
C7 | 0.0554 (2) | 0.7846 (2) | 1.46938 (19) | 0.0420 (4) | |
C8 | 0.22678 (13) | 0.40893 (13) | 0.92523 (13) | 0.0177 (2) | |
C9 | 0.20123 (15) | 0.33882 (15) | 1.07827 (14) | 0.0219 (2) | |
C10 | 0.24750 (16) | 0.18480 (15) | 1.12931 (15) | 0.0248 (3) | |
C11 | 0.31563 (15) | 0.10623 (14) | 1.02734 (15) | 0.0226 (2) | |
C12 | 0.41305 (15) | 0.09891 (14) | 0.75945 (16) | 0.0241 (3) | |
C13 | 0.43480 (16) | 0.17064 (15) | 0.60671 (16) | 0.0274 (3) | |
C14 | 0.38663 (17) | 0.32404 (16) | 0.55448 (15) | 0.0268 (3) | |
C15 | 0.31966 (15) | 0.40423 (14) | 0.65588 (14) | 0.0214 (2) | |
C16 | 0.29733 (13) | 0.33325 (13) | 0.81436 (13) | 0.0175 (2) | |
C17 | 0.34306 (14) | 0.17783 (13) | 0.86778 (14) | 0.0191 (2) | |
H2 | 0.0069 (19) | 0.8441 (18) | 0.9993 (19) | 0.027 (4)* | |
H3 | −0.077 (2) | 0.8780 (18) | 1.2415 (18) | 0.029 (4)* | |
H5 | 0.326 (2) | 0.6496 (19) | 1.3372 (19) | 0.033 (4)* | |
H6 | 0.4121 (19) | 0.6113 (18) | 1.0922 (18) | 0.028 (4)* | |
H7A | 0.141 (3) | 0.802 (3) | 1.502 (3) | 0.069 (7)* | |
H7B | −0.020 (3) | 0.864 (3) | 1.475 (3) | 0.082 (8)* | |
H7C | 0.011 (3) | 0.694 (3) | 1.540 (3) | 0.082 (8)* | |
H9 | 0.1505 (19) | 0.3958 (19) | 1.1459 (19) | 0.028 (4)* | |
H10 | 0.230 (2) | 0.134 (2) | 1.238 (2) | 0.036 (5)* | |
H11 | 0.345 (2) | 0.001 (2) | 1.060 (2) | 0.034 (4)* | |
H12 | 0.4413 (19) | −0.0079 (19) | 0.7957 (18) | 0.027 (4)* | |
H13 | 0.486 (2) | 0.116 (2) | 0.538 (2) | 0.034 (4)* | |
H14 | 0.401 (2) | 0.376 (2) | 0.446 (2) | 0.038 (5)* | |
H15 | 0.285 (2) | 0.5090 (19) | 0.6218 (19) | 0.032 (4)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.02205 (15) | 0.01889 (14) | 0.01668 (14) | −0.00053 (10) | −0.00477 (10) | −0.00807 (10) |
O1 | 0.0202 (4) | 0.0337 (5) | 0.0263 (5) | −0.0023 (4) | −0.0010 (3) | −0.0162 (4) |
O2 | 0.0438 (6) | 0.0219 (4) | 0.0193 (4) | −0.0003 (4) | −0.0128 (4) | −0.0052 (4) |
O3 | 0.0203 (4) | 0.0186 (4) | 0.0253 (4) | 0.0029 (3) | −0.0097 (3) | −0.0110 (3) |
C1 | 0.0189 (5) | 0.0171 (5) | 0.0164 (5) | −0.0004 (4) | −0.0056 (4) | −0.0071 (4) |
C2 | 0.0183 (5) | 0.0209 (5) | 0.0208 (5) | 0.0010 (4) | −0.0078 (4) | −0.0086 (4) |
C3 | 0.0191 (6) | 0.0262 (6) | 0.0235 (6) | 0.0004 (5) | −0.0043 (4) | −0.0114 (5) |
C4 | 0.0280 (6) | 0.0270 (6) | 0.0182 (6) | −0.0031 (5) | −0.0054 (5) | −0.0096 (5) |
C5 | 0.0277 (6) | 0.0254 (6) | 0.0205 (6) | 0.0007 (5) | −0.0121 (5) | −0.0065 (5) |
C6 | 0.0219 (6) | 0.0199 (5) | 0.0221 (6) | 0.0029 (4) | −0.0094 (4) | −0.0076 (4) |
C7 | 0.0485 (10) | 0.0587 (11) | 0.0228 (7) | 0.0058 (8) | −0.0091 (7) | −0.0224 (8) |
C8 | 0.0154 (5) | 0.0178 (5) | 0.0216 (5) | 0.0008 (4) | −0.0057 (4) | −0.0084 (4) |
C9 | 0.0203 (6) | 0.0263 (6) | 0.0205 (6) | −0.0008 (4) | −0.0044 (4) | −0.0105 (5) |
C10 | 0.0246 (6) | 0.0283 (6) | 0.0193 (6) | −0.0027 (5) | −0.0069 (5) | −0.0032 (5) |
C11 | 0.0201 (6) | 0.0188 (6) | 0.0273 (6) | −0.0010 (4) | −0.0086 (5) | −0.0033 (5) |
C12 | 0.0215 (6) | 0.0190 (6) | 0.0339 (7) | 0.0002 (4) | −0.0062 (5) | −0.0129 (5) |
C13 | 0.0279 (6) | 0.0265 (6) | 0.0307 (7) | −0.0019 (5) | −0.0018 (5) | −0.0186 (6) |
C14 | 0.0322 (7) | 0.0274 (6) | 0.0204 (6) | −0.0058 (5) | −0.0019 (5) | −0.0104 (5) |
C15 | 0.0252 (6) | 0.0189 (5) | 0.0195 (6) | −0.0020 (4) | −0.0046 (4) | −0.0067 (4) |
C16 | 0.0160 (5) | 0.0174 (5) | 0.0199 (5) | −0.0013 (4) | −0.0042 (4) | −0.0073 (4) |
C17 | 0.0154 (5) | 0.0181 (5) | 0.0245 (6) | −0.0012 (4) | −0.0055 (4) | −0.0076 (4) |
S1—O2 | 1.4244 (9) | C8—C9 | 1.3659 (17) |
S1—O1 | 1.4296 (9) | C8—C16 | 1.4183 (16) |
S1—O3 | 1.6068 (9) | C9—C10 | 1.4109 (18) |
S1—C1 | 1.7513 (11) | C9—H9 | 0.948 (17) |
O3—C8 | 1.4105 (14) | C10—C11 | 1.3677 (19) |
C1—C2 | 1.3922 (16) | C10—H10 | 0.970 (18) |
C1—C6 | 1.3932 (16) | C11—C17 | 1.4213 (18) |
C2—C3 | 1.3858 (17) | C11—H11 | 0.960 (17) |
C2—H2 | 0.973 (16) | C12—C13 | 1.370 (2) |
C3—C4 | 1.3983 (18) | C12—C17 | 1.4197 (17) |
C3—H3 | 0.968 (17) | C12—H12 | 0.971 (16) |
C4—C5 | 1.3954 (18) | C13—C14 | 1.4115 (19) |
C4—C7 | 1.5036 (19) | C13—H13 | 0.942 (18) |
C5—C6 | 1.3892 (17) | C14—C15 | 1.3732 (17) |
C5—H5 | 0.998 (17) | C14—H14 | 0.976 (18) |
C6—H6 | 0.986 (16) | C15—C16 | 1.4171 (17) |
C7—H7A | 0.96 (3) | C15—H15 | 0.966 (17) |
C7—H7B | 0.94 (3) | C16—C17 | 1.4235 (16) |
C7—H7C | 0.94 (3) | ||
O2—S1—O1 | 120.59 (6) | C9—C8—O3 | 120.41 (10) |
O2—S1—O3 | 103.28 (5) | C9—C8—C16 | 122.80 (11) |
O1—S1—O3 | 108.74 (5) | O3—C8—C16 | 116.58 (10) |
O2—S1—C1 | 109.69 (6) | C8—C9—C10 | 119.05 (11) |
O1—S1—C1 | 109.43 (6) | C8—C9—H9 | 118.1 (10) |
O3—S1—C1 | 103.66 (5) | C10—C9—H9 | 122.8 (10) |
C8—O3—S1 | 119.57 (7) | C11—C10—C9 | 120.58 (12) |
C2—C1—C6 | 121.59 (11) | C11—C10—H10 | 119.6 (11) |
C2—C1—S1 | 118.60 (9) | C9—C10—H10 | 119.9 (11) |
C6—C1—S1 | 119.80 (9) | C10—C11—C17 | 120.96 (11) |
C3—C2—C1 | 118.96 (11) | C10—C11—H11 | 121.6 (10) |
C3—C2—H2 | 119.6 (10) | C17—C11—H11 | 117.4 (10) |
C1—C2—H2 | 121.4 (10) | C13—C12—C17 | 120.62 (12) |
C2—C3—C4 | 120.91 (11) | C13—C12—H12 | 120.4 (9) |
C2—C3—H3 | 119.6 (10) | C17—C12—H12 | 118.9 (10) |
C4—C3—H3 | 119.5 (10) | C12—C13—C14 | 120.52 (12) |
C5—C4—C3 | 118.76 (11) | C12—C13—H13 | 118.2 (11) |
C5—C4—C7 | 121.08 (13) | C14—C13—H13 | 121.2 (11) |
C3—C4—C7 | 120.15 (13) | C15—C14—C13 | 120.45 (12) |
C6—C5—C4 | 121.43 (11) | C15—C14—H14 | 118.6 (11) |
C6—C5—H5 | 119.0 (10) | C13—C14—H14 | 120.9 (11) |
C4—C5—H5 | 119.6 (10) | C14—C15—C16 | 120.20 (12) |
C5—C6—C1 | 118.33 (11) | C14—C15—H15 | 121.3 (10) |
C5—C6—H6 | 121.5 (9) | C16—C15—H15 | 118.5 (10) |
C1—C6—H6 | 120.1 (9) | C15—C16—C8 | 123.02 (11) |
C4—C7—H7A | 112.0 (14) | C15—C16—C17 | 119.52 (11) |
C4—C7—H7B | 112.9 (16) | C8—C16—C17 | 117.44 (11) |
H7A—C7—H7B | 108 (2) | C12—C17—C11 | 122.15 (11) |
C4—C7—H7C | 107.9 (16) | C12—C17—C16 | 118.68 (11) |
H7A—C7—H7C | 106 (2) | C11—C17—C16 | 119.17 (11) |
H7B—C7—H7C | 110 (2) | ||
O2—S1—O3—C8 | 158.11 (8) | O3—C8—C9—C10 | 175.02 (10) |
O1—S1—O3—C8 | 28.90 (10) | C16—C8—C9—C10 | 0.42 (18) |
C1—S1—O3—C8 | −87.46 (9) | C8—C9—C10—C11 | −0.60 (19) |
O2—S1—C1—C2 | 31.33 (11) | C9—C10—C11—C17 | 0.68 (19) |
O1—S1—C1—C2 | 165.71 (9) | C17—C12—C13—C14 | −0.6 (2) |
O3—S1—C1—C2 | −78.42 (10) | C12—C13—C14—C15 | 1.1 (2) |
O2—S1—C1—C6 | −149.58 (10) | C13—C14—C15—C16 | −0.4 (2) |
O1—S1—C1—C6 | −15.20 (12) | C14—C15—C16—C8 | −179.03 (12) |
O3—S1—C1—C6 | 100.67 (10) | C14—C15—C16—C17 | −0.75 (18) |
C6—C1—C2—C3 | −1.04 (18) | C9—C8—C16—C15 | 178.02 (12) |
S1—C1—C2—C3 | 178.04 (9) | O3—C8—C16—C15 | 3.22 (16) |
C1—C2—C3—C4 | 0.28 (19) | C9—C8—C16—C17 | −0.30 (17) |
C2—C3—C4—C5 | 0.78 (19) | O3—C8—C16—C17 | −175.10 (10) |
C2—C3—C4—C7 | −179.17 (14) | C13—C12—C17—C11 | 178.66 (12) |
C3—C4—C5—C6 | −1.2 (2) | C13—C12—C17—C16 | −0.57 (18) |
C7—C4—C5—C6 | 178.80 (14) | C10—C11—C17—C12 | −179.79 (12) |
C4—C5—C6—C1 | 0.43 (19) | C10—C11—C17—C16 | −0.56 (18) |
C2—C1—C6—C5 | 0.68 (18) | C15—C16—C17—C12 | 1.23 (17) |
S1—C1—C6—C5 | −178.38 (9) | C8—C16—C17—C12 | 179.61 (10) |
S1—O3—C8—C9 | 84.39 (12) | C15—C16—C17—C11 | −178.02 (11) |
S1—O3—C8—C16 | −100.68 (10) | C8—C16—C17—C11 | 0.35 (16) |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···O2 | 0.973 (16) | 2.670 (16) | 2.9813 (15) | 99.0 (11) |
C6—H6···O1 | 0.986 (16) | 2.565 (16) | 2.9421 (15) | 102.6 (11) |
C15—H15···O3 | 0.966 (17) | 2.487 (17) | 2.8236 (15) | 100.3 (11) |
C3—H3···O2i | 0.968 (17) | 2.975 (17) | 3.7990 (16) | 143.8 (12) |
C6—H6···O1ii | 0.986 (16) | 2.621 (16) | 3.4334 (15) | 139.8 (12) |
C7—H7A···O2iii | 0.96 (3) | 2.69 (3) | 3.515 (2) | 144.1 (18) |
C9—H9···O3iv | 0.948 (17) | 2.870 (16) | 3.2285 (15) | 103.7 (11) |
C12—H12···O2v | 0.971 (16) | 2.988 (16) | 3.4139 (16) | 107.9 (11) |
C14—H14···O1vi | 0.976 (18) | 2.509 (18) | 3.3231 (16) | 140.8 (14) |
C2—H2···Cg2vii | 0.973 (16) | 2.68 | 3.36 | 127 |
C3—H3···Cg3vii | 0.968 (17) | 2.83 | 3.40 | 119 |
C5—H5···Cg3viii | 0.998 (17) | 2.86 | 3.55 | 127 |
C6—H6···Cg2viii | 0.986 (16) | 3.01 | 3.62 | 121 |
C11—H11···Cg1v | 0.960 (17) | 2.78 | 3.49 | 132 |
Symmetry codes: (i) −x, −y+2, −z+2; (ii) −x+1, −y+1, −z+2; (iii) x, y, z+1; (iv) −x, −y+1, −z+2; (v) x, y−1, z; (vi) −x+1, −y+1, −z+1; (vii) −x, −y+1, −z; (viii) −x+1, −y+1, −z. |
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