Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802014666/cv6134sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802014666/cv6134Isup2.hkl |
CCDC reference: 198325
Compound (I) was prepared as described previously by Gainsford & Woolhouse (2002). Crystals were grown from an ethyl acetate–hexane mixture.
All H atoms were constrained to ride on their parent atom, with a Uiso value 1.2 times the Ueq value of the parent atom.
Data collection: SHELXTL (Siemens, 1983); cell refinement: SHELXTL; data reduction: SHELXTL; program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 in WinGX (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997) and PLATON (Spek, 1990).
Fig. 1. The molecular structure of one of the two independent molecules of (I). Displacement ellipsoids are drawn at the 50% probability level. H atoms have arbitrary radii. |
C13H15NO3S | Z = 4 |
Mr = 265.32 | F(000) = 560 |
Triclinic, P1 | Dx = 1.374 Mg m−3 |
a = 5.282 (4) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.241 (3) Å | Cell parameters from 24 reflections |
c = 22.588 (6) Å | θ = 5.8–14.6° |
α = 79.65 (2)° | µ = 0.25 mm−1 |
β = 89.67 (4)° | T = 130 K |
γ = 76.58 (3)° | Needle, colourless |
V = 1282.4 (11) Å3 | 0.84 × 0.32 × 0.18 mm |
Siemens/Nicolet R3m four-circle diffractometer | Rint = 0.035 |
Radiation source: fine-focus sealed tube | θmax = 22.5°, θmin = 2.3° |
Graphite monochromator | h = 0→5 |
ω scans | k = −11→11 |
3583 measured reflections | l = −24→24 |
3157 independent reflections | 3 standard reflections every 97 reflections |
2378 reflections with I > 2σ(I) | intensity decay: 0.0% |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.057 | H-atom parameters constrained |
wR(F2) = 0.121 | w = 1/[σ2(Fo2) + (0.0097P)2 + 3.7137P] where P = (Fo2 + 2Fc2)/3 |
S = 1.16 | (Δ/σ)max < 0.001 |
3157 reflections | Δρmax = 0.31 e Å−3 |
316 parameters | Δρmin = −0.29 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0068 (8) |
C13H15NO3S | γ = 76.58 (3)° |
Mr = 265.32 | V = 1282.4 (11) Å3 |
Triclinic, P1 | Z = 4 |
a = 5.282 (4) Å | Mo Kα radiation |
b = 11.241 (3) Å | µ = 0.25 mm−1 |
c = 22.588 (6) Å | T = 130 K |
α = 79.65 (2)° | 0.84 × 0.32 × 0.18 mm |
β = 89.67 (4)° |
Siemens/Nicolet R3m four-circle diffractometer | Rint = 0.035 |
3583 measured reflections | θmax = 22.5° |
3157 independent reflections | 3 standard reflections every 97 reflections |
2378 reflections with I > 2σ(I) | intensity decay: 0.0% |
R[F2 > 2σ(F2)] = 0.057 | 0 restraints |
wR(F2) = 0.121 | H-atom parameters constrained |
S = 1.16 | Δρmax = 0.31 e Å−3 |
3157 reflections | Δρmin = −0.29 e Å−3 |
316 parameters |
Experimental. Crystal decay was monitored by repeating the initial 10 frames at the end of the data collection and analyzing duplicate reflections. A standard 1.0 mm diameter collimator was used. |
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. An extinction paramter was refined. |
x | y | z | Uiso*/Ueq | ||
S12 | 0.2613 (2) | 0.69088 (12) | 0.46531 (6) | 0.0227 (4) | |
S22 | 0.2616 (3) | 0.33210 (12) | −0.02285 (6) | 0.0252 (4) | |
O121 | −0.0047 (7) | 0.6840 (3) | 0.46455 (16) | 0.0309 (9) | |
O122 | 0.4493 (6) | 0.6030 (3) | 0.43921 (15) | 0.0253 (9) | |
O15 | 0.3399 (6) | 0.9248 (3) | 0.53905 (15) | 0.0256 (9) | |
O221 | 0.5282 (7) | 0.3370 (3) | −0.01971 (16) | 0.0346 (10) | |
O222 | 0.0758 (7) | 0.4388 (3) | −0.05378 (15) | 0.0276 (9) | |
O25 | 0.2259 (7) | 0.0468 (3) | 0.05684 (17) | 0.0338 (10) | |
N16 | 0.1571 (8) | 0.8792 (4) | 0.57727 (18) | 0.0237 (10) | |
N26 | 0.4029 (8) | 0.0741 (4) | 0.0958 (2) | 0.0319 (11) | |
C11 | 0.3846 (9) | 0.7102 (5) | 0.5373 (2) | 0.0198 (12) | |
H11 | 0.523 (9) | 0.643 (4) | 0.554 (2) | 0.024* | |
C13 | 0.3144 (10) | 0.8471 (5) | 0.4437 (2) | 0.0242 (13) | |
H13 | 0.140 (10) | 0.894 (5) | 0.443 (2) | 0.029* | |
C14 | 0.4592 (10) | 0.8300 (4) | 0.5047 (2) | 0.0198 (12) | |
H14 | 0.644 (9) | 0.827 (4) | 0.503 (2) | 0.024* | |
C17 | 0.1781 (9) | 0.7628 (4) | 0.5775 (2) | 0.0193 (12) | |
C18 | 0.0097 (4) | 0.6945 (2) | 0.61509 (9) | 0.0214 (12) | |
C19 | −0.1806 (6) | 0.7560 (2) | 0.64896 (11) | 0.0262 (13) | |
H19 | −0.2029 | 0.8427 | 0.6480 | 0.031* | |
C110 | −0.3381 (5) | 0.6907 (2) | 0.68425 (11) | 0.0298 (13) | |
H110 | −0.4681 | 0.7328 | 0.7074 | 0.036* | |
C111 | −0.3054 (5) | 0.5639 (2) | 0.68568 (10) | 0.0307 (14) | |
H111 | −0.4131 | 0.5193 | 0.7098 | 0.037* | |
C112 | −0.1152 (6) | 0.5024 (2) | 0.65181 (12) | 0.0261 (13) | |
H112 | −0.0929 | 0.4157 | 0.6528 | 0.031* | |
C113 | 0.0424 (5) | 0.56766 (18) | 0.61652 (10) | 0.0254 (13) | |
H113 | 0.1724 | 0.5256 | 0.5934 | 0.031* | |
C114 | 0.4570 (9) | 0.8744 (4) | 0.38663 (15) | 0.0309 (13) | |
H14A | 0.6102 | 0.8046 | 0.3860 | 0.037* | |
H14B | 0.5217 | 0.9502 | 0.3870 | 0.037* | |
C115 | 0.2907 (12) | 0.8934 (5) | 0.3294 (2) | 0.0397 (15) | |
H15A | 0.1258 | 0.9555 | 0.3320 | 0.048* | |
H15B | 0.2469 | 0.8141 | 0.3256 | 0.048* | |
C116 | 0.4327 (14) | 0.9380 (6) | 0.2741 (3) | 0.057 (2) | |
H16A | 0.4735 | 1.0173 | 0.2775 | 0.068* | |
H16B | 0.3215 | 0.9494 | 0.2379 | 0.068* | |
H16C | 0.5945 | 0.8760 | 0.2711 | 0.068* | |
C21 | 0.1452 (10) | 0.2656 (5) | 0.0489 (2) | 0.0251 (13) | |
H21 | 0.004 (10) | 0.322 (5) | 0.056 (2) | 0.030* | |
C23 | 0.2068 (11) | 0.1887 (5) | −0.0421 (2) | 0.0288 (14) | |
H23 | 0.385 (10) | 0.142 (5) | −0.045 (2) | 0.035* | |
C24 | 0.0845 (11) | 0.1605 (5) | 0.0199 (3) | 0.0283 (13) | |
H24 | −0.096 (10) | 0.160 (4) | 0.019 (2) | 0.034* | |
C27 | 0.3611 (10) | 0.1936 (5) | 0.0931 (2) | 0.0251 (13) | |
C28 | 0.5188 (4) | 0.2460 (2) | 0.13003 (9) | 0.0257 (13) | |
C29 | 0.7282 (6) | 0.1707 (2) | 0.16611 (11) | 0.0321 (14) | |
H29 | 0.7705 | 0.0833 | 0.1674 | 0.039* | |
C210 | 0.8756 (5) | 0.2231 (3) | 0.20023 (11) | 0.0358 (15) | |
H210 | 1.0187 | 0.1717 | 0.2249 | 0.043* | |
C211 | 0.8136 (5) | 0.3509 (3) | 0.19827 (10) | 0.0365 (15) | |
H211 | 0.9144 | 0.3868 | 0.2216 | 0.044* | |
C212 | 0.6042 (6) | 0.4263 (2) | 0.16220 (12) | 0.0325 (14) | |
H212 | 0.5619 | 0.5136 | 0.1609 | 0.039* | |
C213 | 0.4568 (5) | 0.3738 (2) | 0.12808 (11) | 0.0270 (13) | |
H213 | 0.3136 | 0.4253 | 0.1034 | 0.032* | |
C214 | 0.0410 (9) | 0.2064 (4) | −0.09788 (15) | 0.0332 (14) | |
H24A | −0.1185 | 0.2721 | −0.0959 | 0.040* | |
H24B | −0.0130 | 0.1282 | −0.0992 | 0.040* | |
C215 | 0.1773 (12) | 0.2421 (5) | −0.1553 (3) | 0.0440 (16) | |
H25A | 0.2415 | 0.3172 | −0.1530 | 0.053* | |
H25B | 0.3299 | 0.1738 | −0.1590 | 0.053* | |
C216 | 0.0012 (16) | 0.2674 (8) | −0.2102 (3) | 0.087 (3) | |
H26A | −0.0454 | 0.1904 | −0.2155 | 0.105* | |
H26B | 0.0909 | 0.2985 | −0.2457 | 0.105* | |
H26C | −0.1572 | 0.3300 | −0.2053 | 0.105* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S12 | 0.0243 (7) | 0.0209 (8) | 0.0233 (8) | −0.0014 (6) | 0.0018 (6) | −0.0100 (6) |
S22 | 0.0293 (8) | 0.0181 (8) | 0.0259 (8) | −0.0025 (6) | 0.0086 (6) | −0.0018 (6) |
O121 | 0.030 (2) | 0.033 (2) | 0.033 (2) | −0.0068 (17) | 0.0018 (17) | −0.0153 (18) |
O122 | 0.030 (2) | 0.021 (2) | 0.024 (2) | 0.0011 (16) | 0.0039 (16) | −0.0116 (16) |
O15 | 0.036 (2) | 0.021 (2) | 0.022 (2) | −0.0087 (17) | 0.0101 (17) | −0.0091 (16) |
O221 | 0.033 (2) | 0.033 (2) | 0.039 (2) | −0.0113 (18) | 0.0076 (18) | −0.0078 (19) |
O222 | 0.036 (2) | 0.018 (2) | 0.025 (2) | 0.0008 (17) | 0.0047 (17) | −0.0027 (16) |
O25 | 0.043 (2) | 0.016 (2) | 0.039 (2) | −0.0047 (18) | 0.0018 (19) | −0.0004 (18) |
N16 | 0.031 (3) | 0.024 (3) | 0.018 (2) | −0.008 (2) | 0.008 (2) | −0.007 (2) |
N26 | 0.033 (3) | 0.026 (3) | 0.033 (3) | −0.003 (2) | 0.002 (2) | −0.001 (2) |
C11 | 0.020 (3) | 0.016 (3) | 0.026 (3) | −0.003 (2) | 0.000 (2) | −0.011 (2) |
C13 | 0.025 (3) | 0.022 (3) | 0.026 (3) | −0.004 (2) | 0.004 (2) | −0.006 (2) |
C14 | 0.020 (3) | 0.019 (3) | 0.021 (3) | −0.001 (2) | 0.005 (2) | −0.009 (2) |
C17 | 0.024 (3) | 0.013 (3) | 0.019 (3) | −0.002 (2) | −0.001 (2) | −0.003 (2) |
C18 | 0.022 (3) | 0.024 (3) | 0.017 (3) | −0.004 (2) | 0.000 (2) | −0.002 (2) |
C19 | 0.029 (3) | 0.023 (3) | 0.027 (3) | −0.002 (2) | 0.006 (2) | −0.010 (2) |
C110 | 0.032 (3) | 0.033 (3) | 0.025 (3) | −0.006 (3) | 0.005 (3) | −0.008 (3) |
C111 | 0.039 (3) | 0.036 (4) | 0.019 (3) | −0.017 (3) | 0.003 (3) | 0.001 (3) |
C112 | 0.035 (3) | 0.021 (3) | 0.022 (3) | −0.008 (2) | 0.000 (2) | 0.000 (2) |
C113 | 0.027 (3) | 0.023 (3) | 0.024 (3) | −0.001 (2) | 0.001 (2) | −0.008 (2) |
C114 | 0.041 (3) | 0.023 (3) | 0.027 (3) | −0.006 (3) | 0.007 (3) | −0.006 (3) |
C115 | 0.064 (4) | 0.026 (3) | 0.030 (4) | −0.010 (3) | −0.001 (3) | −0.008 (3) |
C116 | 0.087 (5) | 0.049 (4) | 0.023 (4) | 0.004 (4) | 0.007 (3) | −0.004 (3) |
C21 | 0.022 (3) | 0.018 (3) | 0.033 (3) | 0.000 (2) | 0.004 (3) | −0.005 (3) |
C23 | 0.031 (3) | 0.015 (3) | 0.039 (4) | −0.003 (2) | 0.008 (3) | −0.003 (3) |
C24 | 0.026 (3) | 0.019 (3) | 0.038 (4) | −0.002 (2) | 0.002 (3) | −0.004 (3) |
C27 | 0.027 (3) | 0.016 (3) | 0.029 (3) | 0.000 (2) | 0.009 (2) | 0.000 (2) |
C28 | 0.022 (3) | 0.028 (3) | 0.025 (3) | −0.005 (2) | 0.009 (2) | −0.003 (3) |
C29 | 0.030 (3) | 0.034 (3) | 0.025 (3) | 0.001 (3) | 0.004 (3) | 0.001 (3) |
C210 | 0.023 (3) | 0.052 (4) | 0.026 (3) | −0.001 (3) | 0.002 (3) | 0.000 (3) |
C211 | 0.041 (4) | 0.048 (4) | 0.023 (3) | −0.015 (3) | 0.010 (3) | −0.007 (3) |
C212 | 0.040 (3) | 0.030 (3) | 0.028 (3) | −0.012 (3) | 0.010 (3) | −0.002 (3) |
C213 | 0.032 (3) | 0.027 (3) | 0.020 (3) | −0.005 (3) | 0.003 (2) | −0.001 (2) |
C214 | 0.046 (4) | 0.021 (3) | 0.034 (4) | −0.008 (3) | 0.005 (3) | −0.006 (3) |
C215 | 0.069 (5) | 0.026 (3) | 0.035 (4) | −0.005 (3) | 0.009 (3) | −0.007 (3) |
C216 | 0.105 (7) | 0.092 (6) | 0.031 (4) | 0.042 (5) | 0.005 (4) | −0.008 (4) |
S12—O121 | 1.425 (4) | C114—H14B | 0.9900 |
S12—O122 | 1.434 (3) | C115—C116 | 1.522 (8) |
S12—C11 | 1.822 (5) | C115—H15A | 0.9900 |
S12—C13 | 1.822 (5) | C115—H15B | 0.9900 |
S22—O221 | 1.425 (4) | C116—H16A | 0.9800 |
S22—O222 | 1.432 (4) | C116—H16B | 0.9800 |
S22—C21 | 1.825 (5) | C116—H16C | 0.9800 |
S22—C23 | 1.828 (5) | C21—C27 | 1.499 (7) |
O15—N16 | 1.414 (5) | C21—C24 | 1.544 (7) |
O15—C14 | 1.454 (5) | C21—H21 | 0.89 (5) |
O25—N26 | 1.409 (5) | C23—C214 | 1.495 (6) |
O25—C24 | 1.439 (6) | C23—C24 | 1.550 (8) |
N16—C17 | 1.287 (6) | C23—H23 | 0.97 (5) |
N26—C27 | 1.300 (6) | C24—H24 | 0.96 (5) |
C11—C17 | 1.499 (7) | C27—C28 | 1.466 (6) |
C11—C14 | 1.548 (7) | C28—C29 | 1.3900 |
C11—H11 | 0.94 (5) | C28—C213 | 1.3900 |
C13—C114 | 1.509 (6) | C29—C210 | 1.3900 |
C13—C14 | 1.540 (7) | C29—H29 | 0.9500 |
C13—H13 | 0.95 (5) | C210—C211 | 1.3900 |
C14—H14 | 0.97 (5) | C210—H210 | 0.9500 |
C17—C18 | 1.475 (5) | C211—C212 | 1.3900 |
C18—C19 | 1.3900 | C211—H211 | 0.9500 |
C18—C113 | 1.3900 | C212—C213 | 1.3900 |
C19—C110 | 1.3900 | C212—H212 | 0.9500 |
C19—H19 | 0.9500 | C213—H213 | 0.9500 |
C110—C111 | 1.3900 | C214—C215 | 1.516 (7) |
C110—H110 | 0.9500 | C214—H24A | 0.9900 |
C111—C112 | 1.3900 | C214—H24B | 0.9900 |
C111—H111 | 0.9500 | C215—C216 | 1.499 (9) |
C112—C113 | 1.3900 | C215—H25A | 0.9900 |
C112—H112 | 0.9500 | C215—H25B | 0.9900 |
C113—H113 | 0.9500 | C216—H26A | 0.9800 |
C114—C115 | 1.521 (7) | C216—H26B | 0.9800 |
C114—H14A | 0.9900 | C216—H26C | 0.9800 |
O121—S12—O122 | 118.9 (2) | C116—C115—H15B | 109.4 |
O121—S12—C11 | 114.5 (2) | H15A—C115—H15B | 108.0 |
O122—S12—C11 | 110.9 (2) | C115—C116—H16A | 109.5 |
O121—S12—C13 | 114.9 (2) | C115—C116—H16B | 109.5 |
O122—S12—C13 | 110.9 (2) | H16A—C116—H16B | 109.5 |
C11—S12—C13 | 80.5 (2) | C115—C116—H16C | 109.5 |
O221—S22—O222 | 118.8 (2) | H16A—C116—H16C | 109.5 |
O221—S22—C21 | 113.2 (2) | H16B—C116—H16C | 109.5 |
O222—S22—C21 | 112.3 (2) | C27—C21—C24 | 101.0 (4) |
O221—S22—C23 | 114.7 (2) | C27—C21—S22 | 113.2 (4) |
O222—S22—C23 | 111.2 (2) | C24—C21—S22 | 89.7 (3) |
C21—S22—C23 | 80.6 (2) | C27—C21—H21 | 126 (3) |
N16—O15—C14 | 108.5 (3) | C24—C21—H21 | 114 (3) |
N26—O25—C24 | 109.2 (4) | S22—C21—H21 | 106 (3) |
C17—N16—O15 | 110.8 (4) | C214—C23—C24 | 118.5 (5) |
C27—N26—O25 | 110.3 (4) | C214—C23—S22 | 114.9 (4) |
C17—C11—C14 | 100.9 (4) | C24—C23—S22 | 89.4 (3) |
C17—C11—S12 | 114.5 (4) | C214—C23—H23 | 114 (3) |
C14—C11—S12 | 88.9 (3) | C24—C23—H23 | 115 (3) |
C17—C11—H11 | 119 (3) | S22—C23—H23 | 101 (3) |
C14—C11—H11 | 117 (3) | O25—C24—C21 | 105.2 (4) |
S12—C11—H11 | 112 (3) | O25—C24—C23 | 112.7 (4) |
C114—C13—C14 | 118.8 (4) | C21—C24—C23 | 99.5 (4) |
C114—C13—S12 | 117.4 (4) | O25—C24—H24 | 109 (3) |
C14—C13—S12 | 89.1 (3) | C21—C24—H24 | 114 (3) |
C114—C13—H13 | 115 (3) | C23—C24—H24 | 116 (3) |
C14—C13—H13 | 113 (3) | N26—C27—C28 | 120.9 (4) |
S12—C13—H13 | 99 (3) | N26—C27—C21 | 112.8 (5) |
O15—C14—C13 | 111.9 (4) | C28—C27—C21 | 126.3 (4) |
O15—C14—C11 | 104.7 (4) | C29—C28—C213 | 120.0 |
C13—C14—C11 | 99.4 (4) | C29—C28—C27 | 121.3 (2) |
O15—C14—H14 | 108 (3) | C213—C28—C27 | 118.7 (2) |
C13—C14—H14 | 116 (3) | C210—C29—C28 | 120.0 |
C11—C14—H14 | 116 (3) | C210—C29—H29 | 120.0 |
N16—C17—C18 | 120.4 (4) | C28—C29—H29 | 120.0 |
N16—C17—C11 | 113.1 (4) | C29—C210—C211 | 120.0 |
C18—C17—C11 | 126.5 (4) | C29—C210—H210 | 120.0 |
C19—C18—C113 | 120.0 | C211—C210—H210 | 120.0 |
C19—C18—C17 | 120.5 (2) | C212—C211—C210 | 120.0 |
C113—C18—C17 | 119.5 (2) | C212—C211—H211 | 120.0 |
C18—C19—C110 | 120.0 | C210—C211—H211 | 120.0 |
C18—C19—H19 | 120.0 | C211—C212—C213 | 120.0 |
C110—C19—H19 | 120.0 | C211—C212—H212 | 120.0 |
C19—C110—C111 | 120.0 | C213—C212—H212 | 120.0 |
C19—C110—H110 | 120.0 | C212—C213—C28 | 120.0 |
C111—C110—H110 | 120.0 | C212—C213—H213 | 120.0 |
C112—C111—C110 | 120.0 | C28—C213—H213 | 120.0 |
C112—C111—H111 | 120.0 | C23—C214—C215 | 113.4 (4) |
C110—C111—H111 | 120.0 | C23—C214—H24A | 108.9 |
C111—C112—C113 | 120.0 | C215—C214—H24A | 108.9 |
C111—C112—H112 | 120.0 | C23—C214—H24B | 108.9 |
C113—C112—H112 | 120.0 | C215—C214—H24B | 108.9 |
C112—C113—C18 | 120.0 | H24A—C214—H24B | 107.7 |
C112—C113—H113 | 120.0 | C216—C215—C214 | 112.2 (5) |
C18—C113—H113 | 120.0 | C216—C215—H25A | 109.2 |
C13—C114—C115 | 113.8 (4) | C214—C215—H25A | 109.2 |
C13—C114—H14A | 108.8 | C216—C215—H25B | 109.2 |
C115—C114—H14A | 108.8 | C214—C215—H25B | 109.2 |
C13—C114—H14B | 108.8 | H25A—C215—H25B | 107.9 |
C115—C114—H14B | 108.8 | C215—C216—H26A | 109.5 |
H14A—C114—H14B | 107.7 | C215—C216—H26B | 109.5 |
C114—C115—C116 | 111.1 (5) | H26A—C216—H26B | 109.5 |
C114—C115—H15A | 109.4 | C215—C216—H26C | 109.5 |
C116—C115—H15A | 109.4 | H26A—C216—H26C | 109.5 |
C114—C115—H15B | 109.4 | H26B—C216—H26C | 109.5 |
C14—O15—N16—C17 | 9.8 (5) | C14—C13—C114—C115 | −178.2 (4) |
C23—S22—C21—C24 | −6.3 (3) | S12—C13—C114—C115 | 76.5 (5) |
C13—S12—C11—C17 | 91.5 (4) | C13—C114—C115—C116 | 172.1 (5) |
C23—S22—C21—C27 | 95.6 (4) | O221—S22—C21—C27 | −17.3 (5) |
C24—O25—N26—C27 | 9.0 (5) | O222—S22—C21—C27 | −155.3 (4) |
O121—S12—C11—C17 | −21.7 (4) | O221—S22—C21—C24 | −119.1 (3) |
O122—S12—C11—C17 | −159.6 (3) | O222—S22—C21—C24 | 102.9 (3) |
O121—S12—C11—C14 | −123.2 (3) | O221—S22—C23—C214 | −121.0 (4) |
O122—S12—C11—C14 | 98.9 (3) | O222—S22—C23—C214 | 17.3 (5) |
C13—S12—C11—C14 | −10.0 (3) | C21—S22—C23—C214 | 127.7 (4) |
O121—S12—C13—C114 | −114.8 (4) | O221—S22—C23—C24 | 117.6 (3) |
O122—S12—C13—C114 | 23.6 (5) | O222—S22—C23—C24 | −104.1 (3) |
C11—S12—C13—C114 | 132.4 (4) | C21—S22—C23—C24 | 6.2 (3) |
O121—S12—C13—C14 | 122.8 (3) | N26—O25—C24—C21 | −12.3 (5) |
O122—S12—C13—C14 | −98.8 (3) | N26—O25—C24—C23 | 95.1 (5) |
C11—S12—C13—C14 | 10.1 (3) | C27—C21—C24—O25 | 10.7 (5) |
N16—O15—C14—C13 | 92.5 (4) | S22—C21—C24—O25 | 124.2 (4) |
N16—O15—C14—C11 | −14.2 (5) | C27—C21—C24—C23 | −106.2 (4) |
C114—C13—C14—O15 | 116.9 (5) | S22—C21—C24—C23 | 7.4 (4) |
S12—C13—C14—O15 | −121.9 (4) | C214—C23—C24—O25 | 123.4 (5) |
C114—C13—C14—C11 | −133.0 (4) | S22—C23—C24—O25 | −118.4 (4) |
S12—C13—C14—C11 | −11.9 (3) | C214—C23—C24—C21 | −125.6 (5) |
C17—C11—C14—O15 | 12.9 (5) | S22—C23—C24—C21 | −7.4 (4) |
S12—C11—C14—O15 | 127.6 (3) | O25—N26—C27—C28 | 179.4 (4) |
C17—C11—C14—C13 | −102.8 (4) | O25—N26—C27—C21 | −1.4 (6) |
S12—C11—C14—C13 | 11.9 (3) | C24—C21—C27—N26 | −6.0 (6) |
O15—N16—C17—C18 | 179.0 (3) | S22—C21—C27—N26 | −100.4 (5) |
O15—N16—C17—C11 | −0.7 (6) | C24—C21—C27—C28 | 173.2 (4) |
C14—C11—C17—N16 | −7.9 (5) | S22—C21—C27—C28 | 78.8 (5) |
S12—C11—C17—N16 | −101.7 (4) | N26—C27—C28—C29 | 4.3 (5) |
C14—C11—C17—C18 | 172.5 (4) | C21—C27—C28—C29 | −174.8 (4) |
S12—C11—C17—C18 | 78.7 (5) | N26—C27—C28—C213 | −176.3 (4) |
N16—C17—C18—C19 | 2.5 (5) | C21—C27—C28—C213 | 4.5 (6) |
C11—C17—C18—C19 | −177.9 (4) | C213—C28—C29—C210 | 0.0 |
N16—C17—C18—C113 | −177.5 (3) | C27—C28—C29—C210 | 179.4 (3) |
C11—C17—C18—C113 | 2.1 (6) | C28—C29—C210—C211 | 0.0 |
C113—C18—C19—C110 | 0.0 | C29—C210—C211—C212 | 0.0 |
C17—C18—C19—C110 | −180.0 (2) | C210—C211—C212—C213 | 0.0 |
C18—C19—C110—C111 | 0.0 | C211—C212—C213—C28 | 0.0 |
C19—C110—C111—C112 | 0.0 | C29—C28—C213—C212 | 0.0 |
C110—C111—C112—C113 | 0.0 | C27—C28—C213—C212 | −179.4 (2) |
C111—C112—C113—C18 | 0.0 | C24—C23—C214—C215 | 176.0 (4) |
C19—C18—C113—C112 | 0.0 | S22—C23—C214—C215 | 72.3 (5) |
C17—C18—C113—C112 | 180.0 (2) | C23—C214—C215—C216 | −176.2 (5) |
Experimental details
Crystal data | |
Chemical formula | C13H15NO3S |
Mr | 265.32 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 130 |
a, b, c (Å) | 5.282 (4), 11.241 (3), 22.588 (6) |
α, β, γ (°) | 79.65 (2), 89.67 (4), 76.58 (3) |
V (Å3) | 1282.4 (11) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.25 |
Crystal size (mm) | 0.84 × 0.32 × 0.18 |
Data collection | |
Diffractometer | Siemens/Nicolet R3m four-circle diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3583, 3157, 2378 |
Rint | 0.035 |
θmax (°) | 22.5 |
(sin θ/λ)max (Å−1) | 0.538 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.057, 0.121, 1.16 |
No. of reflections | 3157 |
No. of parameters | 316 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.31, −0.29 |
Computer programs: SHELXTL (Siemens, 1983), SHELXTL, SHELXS86 (Sheldrick, 1990), ORTEP-3 in WinGX (Farrugia, 1997), SHELXL97 (Sheldrick, 1997) and PLATON (Spek, 1990).
S12—O121 | 1.425 (4) | S22—O221 | 1.425 (4) |
S12—O122 | 1.434 (3) | O25—N26 | 1.409 (5) |
S12—C11 | 1.822 (5) | N16—C17 | 1.287 (6) |
O121—S12—O122 | 118.9 (2) | C17—N16—O15 | 110.8 (4) |
C11—S12—C13 | 80.5 (2) | C14—C11—S12 | 88.9 (3) |
C14—O15—N16—C17 | 9.8 (5) | C13—S12—C11—C17 | 91.5 (4) |
C23—S22—C21—C24 | −6.3 (3) | C23—S22—C21—C27 | 95.6 (4) |
The title compound, (I), was prepared as part of a study of the use of carnivore odours in mammal pest control. It is closely related to two previously reported structures: exo-7-aza-6-oxa-4-n-propyl-3-thiabicyclo[5.4.11,7.12,5]undecane 3,3-dioxide (Woolhouse et al., 1993) and the exo-stereoisomer exo-7-phenyl-3-n-propyl-5-oxa-2-thia-6-azabicyclo[3.2.01,4]hept-6-ene 2,2-dioxide (Gainsford & Woolhouse, 2002), being formed from a thiete sulfone (Gainsford & Woolhouse, 1994). The crystal structure of (I) consists of two nearly identical independent molecules (one of these is shown in Fig. 1) and their centrosymmetrically related molecules. Most intermolecular interactions are between each independent molecule and their centrosymmetrically related molecules, e.g. C113—H113···O122i, with C113···O122i = 3.303 (5) Å [symmetry code: (i) 1 − x, 1 − y, 1 − z], making two infinite chains along the b crystal axis. The Cj1—Cj4—Oj5—Nj6—Cj7 five-membered rings, where j = 1 or 2, have envelope conformations, with flap atoms Cj4 at distances of 0.222 (7) and 0.185 (8) Å from the four-atom plane for p = 1 and 2, respectively. The four-membered C3S fused rings are not planar, with mean deviations from the mean plane of 0.0787 (3) and 0.0487 (3) Å for j = 1 and 2, respectively. The angles between the mean planes through the two rings are identical at 66.0 (3)°. This is unlike the exo-molecule where the fused four- and five-membered rings are planar (Gainsford & Woolhouse, 2002). The pendant planar phenyl rings Cj8–Cj13 are twisted by 5.2 (2) and 6.9 (3)° for j = 1 and 2, respectively, from their bound five-membered ring. The same comments about the oxygen Oj5 binding in fused-ring systems constructed by cycloaddition apply (see Gainsford & Woolhouse, 2002).