Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806015789/dn2033sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806015789/dn2033Isup2.hkl |
CCDC reference: 610757
Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SIR2002 (Burla et al., 2003); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999).
C16H17NO2S | F(000) = 304 |
Mr = 287.37 | Dx = 1.325 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 25 reflections |
a = 7.7704 (18) Å | θ = 5.9–14.2° |
b = 7.8397 (9) Å | µ = 0.23 mm−1 |
c = 12.0141 (15) Å | T = 173 K |
β = 100.230 (14)° | Prism, yellow |
V = 720.2 (2) Å3 | 0.48 × 0.41 × 0.35 mm |
Z = 2 |
Enraf–Nonius CAD-4 diffractometer | 3185 reflections with I > 2σ(I) |
non–profiled ω/2θ scans | Rint = 0.024 |
Absorption correction: ψ scan (North et al., 1968) | θmax = 27.4°, θmin = 1.7° |
Tmin = 0.900, Tmax = 0.925 | h = −10→10 |
3780 measured reflections | k = −10→10 |
3285 independent reflections | l = −15→15 |
Refinement on F2 | H-atom parameters constrained |
Least-squares matrix: full | w = 1/[σ2(Fo2) + (0.0616P)2 + 0.0994P] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.032 | (Δ/σ)max = 0.001 |
wR(F2) = 0.086 | Δρmax = 0.29 e Å−3 |
S = 1.05 | Δρmin = −0.25 e Å−3 |
3285 reflections | Absolute structure: Flack (1983), 1518 Friedel pairs |
182 parameters | Absolute structure parameter: 0.02 (6) |
1 restraint |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | −0.1014 (2) | 0.2613 (2) | −0.12109 (15) | 0.0310 (3) | |
H1A | −0.1653 | 0.3593 | −0.1586 | 0.046* | |
H1B | −0.173 | 0.2049 | −0.0726 | 0.046* | |
H1C | −0.0758 | 0.1806 | −0.1782 | 0.046* | |
C10 | 0.20900 (18) | 0.42546 (17) | −0.13818 (12) | 0.0202 (3) | |
C11 | 0.14963 (19) | 0.41892 (18) | −0.25468 (12) | 0.0237 (3) | |
H11 | 0.0416 | 0.3645 | −0.2833 | 0.028* | |
C12 | 0.2460 (2) | 0.4907 (2) | −0.32941 (12) | 0.0265 (3) | |
H12 | 0.2036 | 0.4859 | −0.4085 | 0.032* | |
C13 | 0.4046 (2) | 0.5697 (2) | −0.28843 (13) | 0.0265 (3) | |
H13 | 0.4706 | 0.6196 | −0.3394 | 0.032* | |
C14 | 0.46646 (19) | 0.57561 (19) | −0.17284 (12) | 0.0232 (3) | |
H14 | 0.5752 | 0.6293 | −0.1451 | 0.028* | |
C15 | 0.37102 (17) | 0.50387 (17) | −0.09721 (11) | 0.0194 (2) | |
C20 | 0.58546 (18) | 0.48023 (18) | 0.06170 (11) | 0.0211 (3) | |
H20 | 0.6595 | 0.4438 | 0.0113 | 0.025* | |
C21 | 0.65980 (17) | 0.49551 (17) | 0.18222 (11) | 0.0200 (3) | |
C22 | 0.82824 (18) | 0.43370 (17) | 0.21886 (12) | 0.0220 (3) | |
H22 | 0.8923 | 0.384 | 0.1667 | 0.026* | |
C23 | 0.90136 (18) | 0.44576 (18) | 0.33309 (12) | 0.0239 (3) | |
C24 | 0.8091 (2) | 0.5204 (2) | 0.40877 (11) | 0.0253 (3) | |
H24 | 0.8607 | 0.5298 | 0.4864 | 0.03* | |
C25 | 0.64011 (18) | 0.58192 (18) | 0.37093 (11) | 0.0221 (3) | |
C26 | 0.56351 (19) | 0.56879 (18) | 0.25750 (12) | 0.0210 (3) | |
H26 | 0.4479 | 0.6089 | 0.2318 | 0.025* | |
C27 | 1.1601 (2) | 0.2993 (2) | 0.30618 (14) | 0.0342 (4) | |
H27A | 1.2742 | 0.2647 | 0.3489 | 0.051* | |
H27B | 1.1772 | 0.3743 | 0.2438 | 0.051* | |
H27C | 1.0945 | 0.1978 | 0.2757 | 0.051* | |
C28 | 0.3894 (2) | 0.7201 (2) | 0.41768 (13) | 0.0308 (3) | |
H28A | 0.3467 | 0.7661 | 0.4836 | 0.046* | |
H28B | 0.3107 | 0.6295 | 0.3831 | 0.046* | |
H28C | 0.3932 | 0.8113 | 0.3624 | 0.046* | |
N | 0.42604 (16) | 0.51353 (16) | 0.02142 (9) | 0.0217 (2) | |
O1 | 1.06487 (14) | 0.38790 (17) | 0.37906 (10) | 0.0344 (3) | |
O2 | 0.56041 (15) | 0.65213 (17) | 0.45246 (8) | 0.0313 (3) | |
S | 0.09959 (4) | 0.33291 (5) | −0.03654 (3) | 0.02760 (10) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0219 (7) | 0.0321 (7) | 0.0393 (9) | −0.0048 (6) | 0.0062 (6) | −0.0045 (6) |
C10 | 0.0203 (6) | 0.0204 (6) | 0.0200 (6) | 0.0023 (5) | 0.0040 (5) | −0.0024 (5) |
C11 | 0.0223 (7) | 0.0262 (7) | 0.0205 (6) | 0.0012 (5) | −0.0018 (5) | −0.0036 (5) |
C12 | 0.0301 (7) | 0.0298 (7) | 0.0179 (6) | 0.0026 (6) | −0.0005 (5) | −0.0005 (5) |
C13 | 0.0281 (7) | 0.0302 (7) | 0.0219 (7) | 0.0012 (6) | 0.0063 (6) | 0.0042 (6) |
C14 | 0.0223 (6) | 0.0238 (6) | 0.0230 (7) | −0.0005 (5) | 0.0024 (5) | −0.0013 (5) |
C15 | 0.0197 (6) | 0.0208 (6) | 0.0171 (6) | 0.0039 (5) | 0.0013 (5) | −0.0030 (5) |
C20 | 0.0211 (6) | 0.0238 (6) | 0.0187 (6) | −0.0007 (5) | 0.0040 (5) | −0.0025 (5) |
C21 | 0.0206 (6) | 0.0209 (6) | 0.0182 (6) | −0.0030 (5) | 0.0026 (5) | 0.0006 (5) |
C22 | 0.0205 (6) | 0.0249 (7) | 0.0208 (6) | −0.0019 (5) | 0.0042 (5) | 0.0002 (5) |
C23 | 0.0192 (7) | 0.0273 (7) | 0.0236 (7) | −0.0023 (5) | −0.0009 (5) | 0.0041 (5) |
C24 | 0.0255 (7) | 0.0323 (7) | 0.0166 (6) | −0.0036 (6) | −0.0003 (5) | 0.0027 (5) |
C25 | 0.0241 (7) | 0.0250 (6) | 0.0174 (6) | −0.0031 (5) | 0.0044 (5) | −0.0002 (5) |
C26 | 0.0192 (6) | 0.0242 (6) | 0.0190 (6) | −0.0019 (5) | 0.0016 (5) | 0.0002 (5) |
C27 | 0.0234 (7) | 0.0388 (9) | 0.0382 (8) | 0.0067 (6) | −0.0005 (6) | 0.0045 (7) |
C28 | 0.0318 (8) | 0.0367 (8) | 0.0251 (7) | 0.0038 (6) | 0.0083 (6) | −0.0033 (6) |
N | 0.0215 (5) | 0.0264 (6) | 0.0166 (5) | −0.0003 (4) | 0.0014 (4) | −0.0040 (4) |
O1 | 0.0224 (5) | 0.0511 (7) | 0.0268 (5) | 0.0062 (5) | −0.0031 (4) | 0.0019 (5) |
O2 | 0.0320 (5) | 0.0459 (7) | 0.0162 (5) | 0.0041 (5) | 0.0045 (4) | −0.0043 (5) |
S | 0.02517 (17) | 0.03598 (19) | 0.02238 (16) | −0.00458 (15) | 0.00619 (12) | −0.00092 (14) |
C1—S | 1.7955 (16) | C21—C22 | 1.3917 (19) |
C1—H1A | 0.98 | C21—C26 | 1.396 (2) |
C1—H1B | 0.98 | C22—C23 | 1.3922 (19) |
C1—H1C | 0.98 | C22—H22 | 0.95 |
C10—C11 | 1.395 (2) | C23—O1 | 1.3696 (17) |
C10—C15 | 1.4089 (18) | C23—C24 | 1.384 (2) |
C10—S | 1.7633 (14) | C24—C25 | 1.397 (2) |
C11—C12 | 1.387 (2) | C24—H24 | 0.95 |
C11—H11 | 0.95 | C25—O2 | 1.3644 (17) |
C12—C13 | 1.389 (2) | C25—C26 | 1.3906 (19) |
C12—H12 | 0.95 | C26—H26 | 0.95 |
C13—C14 | 1.387 (2) | C27—O1 | 1.424 (2) |
C13—H13 | 0.95 | C27—H27A | 0.98 |
C14—C15 | 1.390 (2) | C27—H27B | 0.98 |
C14—H14 | 0.95 | C27—H27C | 0.98 |
C15—N | 1.4154 (16) | C28—O2 | 1.423 (2) |
C20—N | 1.2744 (19) | C28—H28A | 0.98 |
C20—C21 | 1.4655 (18) | C28—H28B | 0.98 |
C20—H20 | 0.95 | C28—H28C | 0.98 |
S—C1—H1A | 109.5 | C21—C22—H22 | 120.5 |
S—C1—H1B | 109.5 | C23—C22—H22 | 120.5 |
H1A—C1—H1B | 109.5 | O1—C23—C24 | 115.26 (12) |
S—C1—H1C | 109.5 | O1—C23—C22 | 124.19 (14) |
H1A—C1—H1C | 109.5 | C24—C23—C22 | 120.55 (13) |
H1B—C1—H1C | 109.5 | C23—C24—C25 | 119.92 (12) |
C11—C10—C15 | 118.85 (13) | C23—C24—H24 | 120 |
C11—C10—S | 124.44 (11) | C25—C24—H24 | 120 |
C15—C10—S | 116.64 (10) | O2—C25—C26 | 124.30 (13) |
C12—C11—C10 | 120.96 (13) | O2—C25—C24 | 115.21 (12) |
C12—C11—H11 | 119.5 | C26—C25—C24 | 120.49 (13) |
C10—C11—H11 | 119.5 | C25—C26—C21 | 118.69 (13) |
C11—C12—C13 | 119.92 (13) | C25—C26—H26 | 120.7 |
C11—C12—H12 | 120 | C21—C26—H26 | 120.7 |
C13—C12—H12 | 120 | O1—C27—H27A | 109.5 |
C14—C13—C12 | 119.83 (13) | O1—C27—H27B | 109.5 |
C14—C13—H13 | 120.1 | H27A—C27—H27B | 109.5 |
C12—C13—H13 | 120.1 | O1—C27—H27C | 109.5 |
C13—C14—C15 | 120.72 (13) | H27A—C27—H27C | 109.5 |
C13—C14—H14 | 119.6 | H27B—C27—H27C | 109.5 |
C15—C14—H14 | 119.6 | O2—C28—H28A | 109.5 |
C14—C15—C10 | 119.71 (12) | O2—C28—H28B | 109.5 |
C14—C15—N | 122.40 (12) | H28A—C28—H28B | 109.5 |
C10—C15—N | 117.81 (12) | O2—C28—H28C | 109.5 |
N—C20—C21 | 122.99 (13) | H28A—C28—H28C | 109.5 |
N—C20—H20 | 118.5 | H28B—C28—H28C | 109.5 |
C21—C20—H20 | 118.5 | C20—N—C15 | 118.09 (12) |
C22—C21—C26 | 121.37 (13) | C23—O1—C27 | 117.38 (12) |
C22—C21—C20 | 117.88 (12) | C25—O2—C28 | 117.34 (11) |
C26—C21—C20 | 120.75 (12) | C10—S—C1 | 102.41 (7) |
C21—C22—C23 | 118.97 (13) | ||
C15—C10—C11—C12 | −1.2 (2) | O1—C23—C24—C25 | −179.23 (13) |
S—C10—C11—C12 | −178.08 (11) | C22—C23—C24—C25 | 1.0 (2) |
C10—C11—C12—C13 | 0.4 (2) | C23—C24—C25—O2 | 179.62 (13) |
C11—C12—C13—C14 | 0.3 (2) | C23—C24—C25—C26 | 0.0 (2) |
C12—C13—C14—C15 | −0.3 (2) | O2—C25—C26—C21 | 179.41 (14) |
C13—C14—C15—C10 | −0.5 (2) | C24—C25—C26—C21 | −1.0 (2) |
C13—C14—C15—N | −177.29 (13) | C22—C21—C26—C25 | 1.0 (2) |
C11—C10—C15—C14 | 1.21 (19) | C20—C21—C26—C25 | −179.43 (12) |
S—C10—C15—C14 | 178.38 (10) | C21—C20—N—C15 | 176.38 (13) |
C11—C10—C15—N | 178.13 (12) | C14—C15—N—C20 | −46.1 (2) |
S—C10—C15—N | −4.70 (16) | C10—C15—N—C20 | 137.10 (14) |
N—C20—C21—C22 | 171.34 (14) | C24—C23—O1—C27 | 175.65 (14) |
N—C20—C21—C26 | −8.2 (2) | C22—C23—O1—C27 | −4.6 (2) |
C26—C21—C22—C23 | 0.0 (2) | C26—C25—O2—C28 | −1.7 (2) |
C20—C21—C22—C23 | −179.60 (12) | C24—C25—O2—C28 | 178.64 (13) |
C21—C22—C23—O1 | 179.29 (13) | C11—C10—S—C1 | −6.42 (14) |
C21—C22—C23—C24 | −1.0 (2) | C15—C10—S—C1 | 176.59 (11) |