Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680600849X/ob2003sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680600849X/ob2003Isup2.hkl |
CCDC reference: 605139
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.
C16H17NO2S3 | F(000) = 736 |
Mr = 351.52 | Dx = 1.369 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 2190 reflections |
a = 10.2686 (6) Å | θ = 2.4–24.3° |
b = 9.5313 (5) Å | µ = 0.44 mm−1 |
c = 17.5095 (9) Å | T = 298 K |
β = 95.708 (2)° | Plate, colourless |
V = 1705.21 (16) Å3 | 0.25 × 0.22 × 0.08 mm |
Z = 4 |
Bruker SMART APEX CCD area-detector diffractometer | 4071 independent reflections |
Radiation source: fine-focus sealed tube | 2711 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.033 |
Detector resolution: 8.366 pixels mm-1 | θmax = 27.9°, θmin = 2.0° |
φ and ω scans | h = −13→9 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −12→12 |
Tmin = 0.852, Tmax = 0.966 | l = −21→23 |
12197 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)] = 0.056 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.158 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0824P)2 + 0.2134P] where P = (Fo2 + 2Fc2)/3 |
4071 reflections | (Δ/σ)max < 0.001 |
201 parameters | Δρmax = 0.53 e Å−3 |
0 restraints | Δρmin = −0.42 e Å−3 |
Geometry. Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) 0.5254 (0.0124) x - 9.4941 (0.0012) y + 1.1630 (0.0187) z = 0.2050 (0.0213) * -0.0010 (0.0018) C8 * -0.0014 (0.0018) C9 * 0.0031 (0.0019) C10 * -0.0024 (0.0020) C11 * 0.0001 (0.0021) C12 * 0.0016 (0.0020) C13 Rms deviation of fitted atoms = 0.0019 8.6979 (0.0068) x + 3.7995 (0.0118) y + 4.6505 (0.0207) z = 13.7378 (0.0156) Angle to previous plane (with approximate e.s.d.) = 70.82 (0.10) * 0.0022 (0.0020) C1 * -0.0025 (0.0020) C2 * 0.0018 (0.0021) C3 * -0.0009 (0.0022) C4 * 0.0007 (0.0023) C5 * -0.0014 (0.0022) C6 Rms deviation of fitted atoms = 0.0017 |
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 | ||
C1 | 0.7524 (3) | 0.6483 (3) | 1.01796 (15) | 0.0491 (6) | |
C2 | 0.7321 (3) | 0.7569 (3) | 0.96629 (16) | 0.0545 (7) | |
H2 | 0.6889 | 0.8377 | 0.9797 | 0.065* | |
C3 | 0.7754 (3) | 0.7456 (3) | 0.89510 (16) | 0.0606 (7) | |
H3 | 0.7621 | 0.8196 | 0.8606 | 0.073* | |
C4 | 0.8391 (3) | 0.6252 (3) | 0.87340 (16) | 0.0599 (7) | |
C5 | 0.8579 (3) | 0.5183 (3) | 0.92592 (18) | 0.0673 (8) | |
H5 | 0.9006 | 0.4372 | 0.9126 | 0.081* | |
C6 | 0.8152 (3) | 0.5279 (3) | 0.99773 (17) | 0.0633 (8) | |
H6 | 0.8285 | 0.4539 | 1.0323 | 0.076* | |
C7 | 0.8870 (4) | 0.6129 (4) | 0.79526 (19) | 0.0883 (11) | |
H7A | 0.9739 | 0.5745 | 0.8002 | 0.132* | |
H7B | 0.8880 | 0.7041 | 0.7720 | 0.132* | |
H7C | 0.8296 | 0.5523 | 0.7637 | 0.132* | |
C8 | 0.7007 (3) | 0.1469 (3) | 1.05789 (16) | 0.0508 (6) | |
C9 | 0.8352 (3) | 0.1548 (3) | 1.06442 (19) | 0.0652 (8) | |
H9 | 0.8819 | 0.1623 | 1.1125 | 0.078* | |
C10 | 0.9010 (3) | 0.1514 (3) | 0.9987 (2) | 0.0726 (9) | |
H10 | 0.9918 | 0.1584 | 1.0034 | 0.087* | |
C11 | 0.8344 (3) | 0.1377 (3) | 0.92682 (19) | 0.0654 (8) | |
C12 | 0.6998 (3) | 0.1296 (3) | 0.92180 (17) | 0.0630 (8) | |
H12 | 0.6530 | 0.1203 | 0.8738 | 0.076* | |
C13 | 0.6332 (3) | 0.1347 (3) | 0.98588 (16) | 0.0551 (7) | |
H13 | 0.5423 | 0.1301 | 0.9808 | 0.066* | |
C14 | 0.9068 (5) | 0.1323 (4) | 0.8563 (2) | 0.1023 (14) | |
H14A | 0.9749 | 0.2017 | 0.8602 | 0.154* | |
H14B | 0.8471 | 0.1509 | 0.8117 | 0.154* | |
H14C | 0.9447 | 0.0409 | 0.8519 | 0.154* | |
C16 | 0.5500 (3) | 0.5597 (3) | 1.10467 (16) | 0.0532 (6) | |
H16A | 0.5081 | 0.5714 | 1.1515 | 0.064* | |
H16B | 0.4897 | 0.5909 | 1.0619 | 0.064* | |
C15 | 0.5699 (3) | 0.3232 (3) | 1.14504 (14) | 0.0478 (6) | |
N1 | 0.5828 (2) | 0.4138 (2) | 1.09475 (12) | 0.0509 (5) | |
O1 | 0.6585 (2) | 0.8043 (2) | 1.12088 (11) | 0.0654 (6) | |
O2 | 0.7909 (2) | 0.5972 (2) | 1.16436 (11) | 0.0731 (6) | |
S1 | 0.69735 (7) | 0.66232 (7) | 1.10953 (4) | 0.0519 (2) | |
S2 | 0.61618 (9) | 0.14789 (8) | 1.14109 (4) | 0.0660 (3) | |
S3 | 0.49679 (9) | 0.35188 (9) | 1.23050 (4) | 0.0685 (3) | |
H1A | 0.468 (3) | 0.249 (4) | 1.2558 (17) | 0.103* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0488 (15) | 0.0456 (14) | 0.0533 (14) | −0.0017 (11) | 0.0072 (12) | −0.0020 (11) |
C2 | 0.0522 (15) | 0.0468 (15) | 0.0652 (16) | 0.0049 (12) | 0.0101 (13) | 0.0045 (13) |
C3 | 0.0592 (17) | 0.0636 (19) | 0.0594 (16) | 0.0059 (14) | 0.0084 (14) | 0.0137 (14) |
C4 | 0.0549 (17) | 0.071 (2) | 0.0552 (16) | −0.0034 (14) | 0.0104 (13) | −0.0002 (14) |
C5 | 0.079 (2) | 0.0563 (18) | 0.0712 (19) | 0.0143 (15) | 0.0281 (17) | −0.0007 (14) |
C6 | 0.079 (2) | 0.0463 (16) | 0.0675 (18) | 0.0139 (14) | 0.0231 (16) | 0.0104 (13) |
C7 | 0.097 (3) | 0.109 (3) | 0.0628 (19) | 0.014 (2) | 0.0274 (19) | 0.0038 (19) |
C8 | 0.0588 (17) | 0.0372 (13) | 0.0573 (15) | 0.0051 (11) | 0.0103 (13) | 0.0058 (11) |
C9 | 0.0594 (18) | 0.066 (2) | 0.0682 (18) | 0.0050 (14) | −0.0039 (15) | −0.0040 (15) |
C10 | 0.0531 (17) | 0.069 (2) | 0.097 (3) | 0.0013 (14) | 0.0143 (18) | −0.0121 (17) |
C11 | 0.078 (2) | 0.0461 (16) | 0.076 (2) | 0.0054 (14) | 0.0296 (18) | −0.0004 (14) |
C12 | 0.074 (2) | 0.0600 (18) | 0.0546 (16) | 0.0056 (14) | 0.0063 (15) | 0.0002 (13) |
C13 | 0.0505 (16) | 0.0533 (16) | 0.0615 (17) | 0.0048 (12) | 0.0056 (13) | 0.0021 (12) |
C14 | 0.126 (3) | 0.093 (3) | 0.099 (3) | −0.001 (2) | 0.064 (3) | −0.009 (2) |
C16 | 0.0572 (16) | 0.0494 (15) | 0.0552 (15) | 0.0029 (12) | 0.0172 (13) | −0.0044 (12) |
C15 | 0.0538 (15) | 0.0542 (15) | 0.0364 (12) | −0.0034 (12) | 0.0091 (11) | −0.0020 (11) |
N1 | 0.0625 (14) | 0.0440 (12) | 0.0485 (12) | 0.0025 (10) | 0.0171 (10) | −0.0018 (10) |
O1 | 0.0869 (15) | 0.0471 (11) | 0.0638 (12) | −0.0006 (10) | 0.0149 (11) | −0.0119 (9) |
O2 | 0.0792 (14) | 0.0770 (15) | 0.0594 (12) | 0.0051 (12) | −0.0113 (11) | −0.0011 (11) |
S1 | 0.0605 (4) | 0.0472 (4) | 0.0481 (4) | 0.0015 (3) | 0.0057 (3) | −0.0046 (3) |
S2 | 0.0895 (6) | 0.0518 (4) | 0.0596 (4) | 0.0051 (4) | 0.0226 (4) | 0.0132 (3) |
S3 | 0.0867 (6) | 0.0829 (6) | 0.0387 (4) | 0.0018 (4) | 0.0213 (4) | 0.0006 (3) |
C1—C2 | 1.377 (4) | C10—C11 | 1.377 (5) |
C1—C6 | 1.380 (4) | C10—H10 | 0.9300 |
C1—S1 | 1.758 (3) | C11—C12 | 1.378 (5) |
C2—C3 | 1.369 (4) | C11—C14 | 1.505 (5) |
C2—H2 | 0.9300 | C12—C13 | 1.371 (4) |
C3—C4 | 1.392 (4) | C12—H12 | 0.9300 |
C3—H3 | 0.9300 | C13—H13 | 0.9300 |
C4—C5 | 1.374 (4) | C14—H14A | 0.9600 |
C4—C7 | 1.504 (4) | C14—H14B | 0.9600 |
C5—C6 | 1.375 (4) | C14—H14C | 0.9600 |
C5—H5 | 0.9300 | C16—N1 | 1.445 (3) |
C6—H6 | 0.9300 | C16—S1 | 1.796 (3) |
C7—H7A | 0.9600 | C16—H16A | 0.9700 |
C7—H7B | 0.9600 | C16—H16B | 0.9700 |
C7—H7C | 0.9600 | C15—N1 | 1.250 (3) |
C8—C9 | 1.377 (4) | C15—S2 | 1.741 (3) |
C8—C13 | 1.382 (4) | C15—S3 | 1.761 (2) |
C8—S2 | 1.768 (3) | O1—S1 | 1.430 (2) |
C9—C10 | 1.392 (5) | O2—S1 | 1.430 (2) |
C9—H9 | 0.9300 | S3—H1A | 1.13 (4) |
C2—C1—C6 | 120.1 (3) | C10—C11—C12 | 117.9 (3) |
C2—C1—S1 | 120.0 (2) | C10—C11—C14 | 120.8 (3) |
C6—C1—S1 | 119.9 (2) | C12—C11—C14 | 121.3 (3) |
C1—C2—C3 | 119.8 (3) | C13—C12—C11 | 121.6 (3) |
C1—C2—H2 | 120.0 | C13—C12—H12 | 119.2 |
C3—C2—H2 | 120.2 | C11—C12—H12 | 119.2 |
C2—C3—C4 | 121.2 (3) | C12—C13—C8 | 120.3 (3) |
C2—C3—H3 | 119.4 | C12—C13—H13 | 119.9 |
C4—C3—H3 | 119.4 | C8—C13—H13 | 119.8 |
C5—C4—C3 | 117.8 (3) | C11—C14—H14A | 109.5 |
C5—C4—C7 | 121.0 (3) | C11—C14—H14B | 109.6 |
C3—C4—C7 | 121.2 (3) | H14A—C14—H14B | 109.5 |
C4—C5—C6 | 121.8 (3) | C11—C14—H14C | 109.3 |
C4—C5—H5 | 119.1 | H14A—C14—H14C | 109.5 |
C6—C5—H5 | 119.1 | H14B—C14—H14C | 109.5 |
C5—C6—C1 | 119.3 (3) | N1—C16—S1 | 108.94 (18) |
C5—C6—H6 | 120.4 | N1—C16—H16A | 109.9 |
C1—C6—H6 | 120.3 | S1—C16—H16A | 109.9 |
C4—C7—H7A | 109.3 | N1—C16—H16B | 109.9 |
C4—C7—H7B | 109.6 | S1—C16—H16B | 109.9 |
H7A—C7—H7B | 109.5 | H16A—C16—H16B | 108.3 |
C4—C7—H7C | 109.5 | N1—C15—S2 | 125.9 (2) |
H7A—C7—H7C | 109.5 | N1—C15—S3 | 125.1 (2) |
H7B—C7—H7C | 109.5 | S2—C15—S3 | 108.89 (14) |
C9—C8—C13 | 119.2 (3) | C15—N1—C16 | 122.5 (2) |
C9—C8—S2 | 120.1 (2) | O2—S1—O1 | 119.67 (13) |
C13—C8—S2 | 120.7 (2) | O2—S1—C1 | 108.89 (13) |
C8—C9—C10 | 119.7 (3) | O1—S1—C1 | 108.57 (12) |
C8—C9—H9 | 120.2 | O2—S1—C16 | 107.57 (14) |
C10—C9—H9 | 120.1 | O1—S1—C16 | 106.06 (13) |
C11—C10—C9 | 121.3 (3) | C1—S1—C16 | 105.14 (12) |
C11—C10—H10 | 119.4 | C15—S2—C8 | 101.31 (12) |
C9—C10—H10 | 119.3 | C15—S3—H1A | 110.7 (16) |
C6—C1—C2—C3 | −0.7 (4) | C9—C8—C13—C12 | 0.5 (4) |
S1—C1—C2—C3 | 179.8 (2) | S2—C8—C13—C12 | −177.9 (2) |
C1—C2—C3—C4 | 0.6 (5) | S2—C15—N1—C16 | −175.6 (2) |
C2—C3—C4—C5 | −0.4 (5) | S3—C15—N1—C16 | 6.5 (4) |
C2—C3—C4—C7 | −179.9 (3) | S1—C16—N1—C15 | 113.3 (3) |
C3—C4—C5—C6 | 0.3 (5) | C2—C1—S1—O2 | −142.9 (2) |
C7—C4—C5—C6 | 179.8 (3) | C6—C1—S1—O2 | 37.6 (3) |
C4—C5—C6—C1 | −0.3 (5) | C2—C1—S1—O1 | −11.1 (3) |
C2—C1—C6—C5 | 0.5 (5) | C6—C1—S1—O1 | 169.4 (2) |
S1—C1—C6—C5 | −180.0 (3) | C2—C1—S1—C16 | 102.1 (2) |
C13—C8—C9—C10 | 0.4 (4) | C6—C1—S1—C16 | −77.4 (3) |
S2—C8—C9—C10 | 178.8 (2) | N1—C16—S1—O2 | −49.7 (2) |
C8—C9—C10—C11 | −1.2 (4) | N1—C16—S1—O1 | −178.85 (17) |
C9—C10—C11—C12 | 0.9 (5) | N1—C16—S1—C1 | 66.2 (2) |
C9—C10—C11—C14 | −179.2 (3) | N1—C15—S2—C8 | 7.6 (3) |
C10—C11—C12—C13 | 0.0 (4) | S3—C15—S2—C8 | −174.24 (14) |
C14—C11—C12—C13 | −179.8 (3) | C9—C8—S2—C15 | 98.2 (2) |
C11—C12—C13—C8 | −0.7 (4) | C13—C8—S2—C15 | −83.4 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
S3—H1A···O1i | 1.13 (4) | 2.68 (3) | 3.219 (2) | 108 (2) |
C13—H13···O1ii | 0.93 | 2.66 | 3.420 (4) | 139 |
C2—H2···Cg1iii | 0.93 | 3.02 | 3.717 (2) | 133 |
Symmetry codes: (i) −x+1, y−1/2, −z+5/2; (ii) −x+1, −y+1, −z+2; (iii) x, y+1, z. |