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Information on the geometrical structures of α-(p-phenylsulfinyl)-p-substituted acetophenones X—PhC(O)CH2S(O)Ph—Y [X = OMe, Y = H (1); X = NO2, Y = OMe (2); X = OMe, Y = NO2 (3); IUPAC names: (1) 4-methoxyphenyl phenylsulfinylmethyl ketone; (2) 4-nitrophenyl 4-methoxyphenylsulfinylmethyl ketone; (3) 4-methoxyphenyl 4-nitrophenylsulfinylmethyl ketone] have been obtained from X-ray diffraction analyses. A comparison of these results with those previously obtained from X-ray diffraction and ab initio computations of α-methylsulfinylacetophenone, PhC(O)CH2­S(O)Me, indicated that (1) and (2) adopt in the crystal a cis1 conformation and (3) assumes a quasi-gauche geometry. The stabilization of these conformations in the crystal is discussed in terms of the dipole moment coupling, Coulombic and intramolecular charge transfer interactions between the oppositely charged atoms of the C=O and S=O dipoles. The p-substituted benzene ring is quasi-coplanar with the sulfinyl group for (1) and (3), but is quasi-perpendicular for (2). Conjugation and repulsion between the sulfinyl sulfur lone pair and the π-benzene ring seem to be responsible for the observed geometries.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768199008599/na0095sup1.cif
Contains datablocks default, 1, 2, 3

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768199008599/na00951sup2.hkl
Contains datablock 1

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768199008599/na00952sup3.hkl
Contains datablock 2

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768199008599/na00953sup4.hkl
Contains datablock 3

CCDC references: 141658; 141659; 141660

Computing details top

For all compounds, data collection: CAD-4 Software (Enraf-Nonius,1989); cell refinement: CAD-4 Software (Enraf-Nonius,1989); data reduction: MolEN (Fair, 1990); program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP (Zsolnai, 1995); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997) and PARST95 (Nardelli, 1995).

(1) top
Crystal data top
C15H14O3SF(000) = 1152
Mr = 274.32Dx = 1.345 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 10.4698 (9) ÅCell parameters from 20 reflections
b = 10.2770 (9) Åθ = 8.1–12.0°
c = 25.449 (2) ŵ = 0.24 mm1
β = 98.429 (1)°T = 293 K
V = 2708.7 (4) Å3Irregular, colorless
Z = 80.25 × 0.22 × 0.10 mm
Data collection top
Enraf-Nonius CAD-4
diffractometer
Rint = 0.133
Radiation source: fine-focus sealed tubeθmax = 21.6°
Graphite monochromatorh = 1010
ω/2θ scansk = 010
3670 measured reflectionsl = 260
3162 independent reflections3 standard reflections every 60 min
1198 reflections with F2 > 2σF2 intensity decay: 1.0%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.057Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104H-atom parameters constrained
S = 0.93Calculated w = 1/[σ2(Fo2) + (0.0495)2]
where P = (Fo2 + 2Fc2)/3
3162 reflections(Δ/σ)max < 0.001
355 parametersΔρmax = 0.35 e Å3
0 restraintsΔρmin = 0.22 e Å3
Special details top

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 on F2 for ALL reflections except for 0 with very negative F2 or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating _R_factor_obs 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
S10.4424 (2)0.5124 (2)0.08843 (11)0.0670 (7)
O11A0.4005 (9)0.5241 (9)0.0278 (4)0.110 (4)0.624 (9)
O11B0.3817 (12)0.5572 (12)0.1394 (5)0.070 (6)0.376 (9)
O120.5423 (5)0.7658 (5)0.0813 (2)0.079 (2)
O131.1150 (6)0.8703 (5)0.0486 (2)0.0714 (17)
C110.6109 (6)0.5493 (7)0.0981 (3)0.066 (2)
H11A0.64740.53090.13460.079*
H11B0.65420.49460.07520.079*
C120.6331 (8)0.6910 (8)0.0859 (3)0.056 (2)
C130.7627 (7)0.7312 (8)0.0775 (3)0.049 (2)
C140.7783 (7)0.8537 (8)0.0555 (3)0.052 (2)
H140.70690.90770.04710.062*
C150.8949 (8)0.8946 (7)0.0463 (3)0.055 (2)
H150.90260.97540.03050.066*
C161.0035 (8)0.8186 (9)0.0598 (3)0.056 (2)
C170.9900 (8)0.6989 (8)0.0830 (3)0.061 (2)
H171.06240.64750.09330.073*
C180.8707 (8)0.6556 (7)0.0909 (3)0.059 (2)
H180.86270.57360.10550.071*
C190.4596 (6)0.3407 (8)0.1012 (4)0.054 (2)
C1100.4676 (8)0.2540 (11)0.0612 (4)0.074 (3)
H1100.47430.28250.02700.089*
C1110.4655 (9)0.1240 (12)0.0728 (5)0.102 (4)
H1110.47170.06310.04630.123*
C1120.4546 (9)0.0835 (12)0.1221 (7)0.109 (5)
H1120.45220.00530.12900.130*
C1130.4469 (9)0.1692 (16)0.1626 (5)0.110 (5)
H1130.44110.14040.19680.132*
C1140.4482 (8)0.3003 (11)0.1507 (4)0.077 (3)
H1140.44120.36130.17720.093*
C1151.2303 (7)0.7942 (8)0.0586 (3)0.094 (3)
H11C1.22120.71780.03660.141*
H11D1.24510.76890.09530.141*
H11E1.30220.84480.05060.141*
S20.7232 (2)0.8156 (3)0.24842 (10)0.0794 (8)
O210.7222 (6)0.6853 (6)0.2174 (3)0.117 (2)
O220.9668 (5)0.8952 (6)0.2201 (2)0.100 (2)
O230.9938 (5)1.3565 (5)0.0560 (2)0.0660 (16)
C210.7418 (6)0.9409 (7)0.2009 (3)0.049 (2)
H21A0.69460.91660.16660.059*
H21B0.70521.02140.21190.059*
C220.8825 (8)0.9626 (8)0.1955 (3)0.060 (2)
C230.9125 (8)1.0675 (8)0.1597 (3)0.052 (2)
C240.8173 (7)1.1452 (8)0.1308 (3)0.051 (2)
H240.73131.13230.13470.062*
C250.8480 (7)1.2393 (8)0.0971 (3)0.058 (2)
H250.78271.28980.07860.070*
C260.9746 (8)1.2611 (8)0.0899 (3)0.048 (2)
C271.0704 (7)1.1840 (9)0.1177 (3)0.059 (2)
H271.15601.19590.11290.071*
C281.0397 (8)1.0901 (9)0.1524 (3)0.063 (2)
H281.10541.04070.17130.075*
C290.5597 (7)0.8503 (9)0.2517 (3)0.055 (2)
C2100.4619 (12)0.7759 (9)0.2247 (4)0.088 (3)
H2100.48120.70660.20370.106*
C2110.3321 (12)0.8058 (14)0.2290 (5)0.111 (4)
H2110.26450.75600.21170.133*
C2120.3091 (11)0.9105 (15)0.2596 (5)0.102 (4)
H2120.22420.93370.26160.122*
C2130.4053 (14)0.9809 (11)0.2867 (4)0.099 (3)
H2130.38771.04910.30860.119*
C2140.5283 (9)0.9501 (10)0.2814 (3)0.075 (3)
H2140.59471.00070.29910.089*
C2151.1239 (7)1.3873 (7)0.0503 (3)0.076 (3)
H21C1.16261.31430.03520.114*
H21D1.17161.40690.08450.114*
H21E1.12491.46140.02740.114*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0554 (14)0.0521 (16)0.092 (2)0.0002 (12)0.0075 (14)0.0074 (15)
O11A0.136 (9)0.091 (8)0.087 (9)0.038 (7)0.034 (6)0.036 (6)
O11B0.066 (10)0.055 (10)0.097 (13)0.004 (8)0.038 (9)0.019 (9)
O120.066 (4)0.047 (4)0.131 (6)0.011 (3)0.035 (4)0.007 (4)
O130.054 (4)0.054 (4)0.106 (5)0.001 (3)0.008 (3)0.007 (3)
C110.062 (6)0.049 (6)0.088 (6)0.001 (5)0.011 (5)0.003 (5)
C120.071 (7)0.039 (6)0.059 (6)0.001 (5)0.013 (5)0.003 (5)
C130.048 (6)0.047 (6)0.051 (6)0.000 (5)0.003 (5)0.002 (5)
C140.044 (5)0.045 (6)0.065 (6)0.010 (4)0.007 (4)0.002 (5)
C150.061 (6)0.029 (5)0.077 (7)0.006 (5)0.016 (5)0.003 (4)
C160.041 (5)0.048 (6)0.078 (7)0.010 (5)0.008 (5)0.002 (5)
C170.062 (6)0.044 (6)0.074 (7)0.009 (5)0.004 (5)0.004 (5)
C180.060 (6)0.047 (6)0.069 (6)0.007 (5)0.004 (5)0.018 (5)
C190.047 (5)0.063 (7)0.054 (6)0.001 (4)0.012 (4)0.031 (6)
C1100.102 (8)0.066 (8)0.050 (7)0.019 (6)0.000 (6)0.006 (6)
C1110.097 (8)0.054 (9)0.136 (12)0.019 (7)0.047 (8)0.022 (7)
C1120.047 (6)0.079 (10)0.189 (16)0.012 (6)0.017 (9)0.063 (11)
C1130.078 (7)0.157 (15)0.097 (11)0.019 (9)0.024 (7)0.065 (10)
C1140.080 (7)0.068 (8)0.087 (9)0.011 (6)0.023 (6)0.010 (7)
C1150.055 (6)0.093 (7)0.136 (9)0.001 (6)0.019 (6)0.014 (7)
S20.0642 (16)0.095 (2)0.0813 (18)0.0186 (15)0.0173 (13)0.0354 (17)
O210.164 (6)0.054 (4)0.143 (6)0.032 (4)0.058 (5)0.015 (4)
O220.068 (4)0.137 (6)0.097 (5)0.028 (4)0.013 (4)0.055 (5)
O230.049 (4)0.057 (4)0.093 (5)0.005 (3)0.013 (3)0.016 (4)
C210.046 (5)0.053 (5)0.050 (5)0.005 (4)0.015 (4)0.005 (4)
C220.061 (6)0.065 (7)0.051 (6)0.010 (5)0.002 (5)0.002 (5)
C230.052 (6)0.058 (6)0.042 (5)0.003 (5)0.001 (5)0.003 (5)
C240.039 (5)0.048 (6)0.067 (6)0.004 (4)0.006 (5)0.015 (5)
C250.037 (5)0.055 (6)0.084 (7)0.001 (4)0.014 (5)0.006 (5)
C260.043 (6)0.042 (6)0.059 (6)0.007 (5)0.002 (5)0.003 (5)
C270.038 (5)0.071 (6)0.067 (6)0.009 (5)0.005 (5)0.022 (5)
C280.047 (6)0.079 (7)0.060 (6)0.008 (5)0.001 (5)0.005 (6)
C290.051 (6)0.067 (7)0.047 (6)0.016 (5)0.012 (5)0.015 (5)
C2100.093 (8)0.083 (8)0.091 (8)0.029 (7)0.022 (7)0.013 (6)
C2110.088 (10)0.123 (12)0.116 (11)0.059 (9)0.006 (8)0.039 (9)
C2120.064 (8)0.142 (13)0.100 (11)0.002 (9)0.016 (8)0.052 (9)
C2130.122 (10)0.119 (10)0.060 (8)0.029 (10)0.026 (8)0.012 (7)
C2140.067 (7)0.094 (9)0.068 (7)0.025 (6)0.026 (5)0.020 (6)
C2150.062 (6)0.066 (6)0.102 (7)0.023 (5)0.018 (5)0.013 (5)
Geometric parameters (Å, º) top
S1—O11A1.546 (9)S2—O211.553 (6)
S1—O11B1.593 (12)S2—C291.763 (7)
S1—C111.785 (7)S2—C211.797 (7)
S1—C191.799 (8)O22—C221.220 (8)
O12—C121.215 (8)O23—C261.341 (8)
O13—C161.350 (8)O23—C2151.425 (7)
O13—C1151.430 (8)C21—C221.516 (9)
C11—C121.515 (10)C22—C231.475 (10)
C12—C131.463 (9)C23—C281.391 (9)
C13—C181.373 (9)C23—C241.399 (9)
C13—C141.397 (9)C24—C251.363 (9)
C14—C151.345 (8)C25—C261.382 (9)
C15—C161.381 (9)C26—C271.388 (9)
C16—C171.381 (10)C27—C281.376 (9)
C17—C181.368 (9)C29—C2141.342 (10)
C19—C1141.348 (10)C29—C2101.378 (10)
C19—C1101.366 (10)C210—C2111.413 (12)
C110—C1111.369 (12)C211—C2121.369 (13)
C111—C1121.344 (13)C212—C2131.346 (12)
C112—C1131.365 (13)C213—C2141.352 (10)
C113—C1141.381 (13)
O11A—S1—O11B134.5 (6)C19—C114—C113120.6 (10)
O11A—S1—C11104.6 (4)O21—S2—C29105.3 (5)
O11B—S1—C11109.3 (5)O21—S2—C21105.6 (3)
O11A—S1—C19105.3 (5)C29—S2—C2195.1 (3)
O11B—S1—C19100.2 (6)C26—O23—C215117.6 (6)
C11—S1—C1996.5 (3)C22—C21—S2111.7 (5)
C16—O13—C115118.8 (6)O22—C22—C23121.9 (8)
C12—C11—S1110.8 (5)O22—C22—C21120.6 (8)
O12—C12—C13122.5 (8)C23—C22—C21117.5 (7)
O12—C12—C11119.1 (8)C28—C23—C24117.2 (8)
C13—C12—C11118.4 (7)C28—C23—C22120.0 (8)
C18—C13—C14118.0 (7)C24—C23—C22122.8 (8)
C18—C13—C12123.5 (8)C25—C24—C23121.3 (8)
C14—C13—C12118.5 (7)C24—C25—C26121.2 (8)
C15—C14—C13121.0 (7)O23—C26—C25116.2 (7)
C14—C15—C16121.0 (7)O23—C26—C27125.5 (8)
O13—C16—C15115.5 (8)C25—C26—C27118.4 (8)
O13—C16—C17125.9 (8)C28—C27—C26120.5 (7)
C15—C16—C17118.6 (7)C27—C28—C23121.4 (8)
C18—C17—C16120.4 (8)C214—C29—C210118.7 (8)
C17—C18—C13121.0 (8)C214—C29—S2120.0 (8)
C114—C19—C110121.4 (8)C210—C29—S2121.3 (9)
C114—C19—S1116.8 (9)C29—C210—C211119.5 (10)
C110—C19—S1121.3 (8)C212—C211—C210117.8 (11)
C19—C110—C111118.0 (9)C213—C212—C211122.2 (13)
C112—C111—C110120.7 (11)C212—C213—C214118.3 (11)
C111—C112—C113121.8 (13)C29—C214—C213123.4 (10)
C112—C113—C114117.5 (12)
(2) top
Crystal data top
C15H13NO5SDx = 1.455 Mg m3
Mr = 319.32Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 25 reflections
a = 5.5704 (8) Åθ = 8.2–13.4°
b = 8.619 (1) ŵ = 0.25 mm1
c = 30.356 (5) ÅT = 293 K
V = 1457.4 (4) Å3Irregular, colorless
Z = 40.20 × 0.15 × 0.08 mm
F(000) = 664
Data collection top
Enraf-Nonius CAD-4
diffractometer
θmax = 25.5°
Radiation source: fine-focus sealed tubeh = 06
Graphite monochromatork = 010
ω/2θ scansl = 036
1615 measured reflections3 standard reflections every 60 min
1615 independent reflections intensity decay: 0.4%
688 reflections with F2 > 2σF2
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.107H-atom parameters constrained
wR(F2) = 0.289Calculated w = 1/[σ2(Fo2) + (0.2000)2]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max = 0.003
1615 reflectionsΔρmax = 1.55 e Å3
201 parametersΔρmin = 0.51 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.003 (7)
Special details top

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 on F2 for ALL reflections except for 0 with very negative F2 or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating _R_factor_obs 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N0.856 (4)0.6354 (19)0.9621 (4)0.101 (6)
S0.8418 (7)1.0154 (4)0.71316 (13)0.0682 (13)
O10.7068 (17)1.1627 (8)0.7236 (3)0.056 (2)
O21.119 (2)1.0406 (10)0.7911 (3)0.075 (3)
O30.259 (3)0.6749 (16)0.5806 (4)0.122 (5)
O40.714 (5)0.5394 (16)0.9655 (4)0.167 (10)
O50.989 (3)0.6837 (18)0.9910 (5)0.133 (6)
C10.816 (3)0.8958 (17)0.7585 (4)0.070 (4)
H1A0.64920.89400.76780.084*
H1B0.85980.79110.75000.084*
C20.963 (3)0.9431 (14)0.7953 (4)0.047 (3)
C30.932 (2)0.8617 (13)0.8390 (4)0.046 (3)
C40.733 (3)0.7620 (14)0.8456 (4)0.052 (3)
H40.61990.74200.82380.062*
C50.720 (3)0.6925 (17)0.8900 (5)0.075 (5)
H50.59570.62510.89710.090*
C60.891 (3)0.7276 (16)0.9205 (5)0.061 (4)
C71.074 (3)0.8214 (17)0.9133 (4)0.067 (4)
H71.18720.83860.93530.080*
C81.096 (3)0.8950 (16)0.8724 (4)0.059 (4)
H81.21970.96560.86750.071*
C90.665 (3)0.9074 (14)0.6742 (5)0.058 (4)
C100.761 (3)0.8969 (19)0.6310 (6)0.077 (5)
H100.90680.94320.62380.092*
C110.629 (4)0.814 (2)0.5999 (5)0.085 (6)
H110.69180.80160.57170.102*
C120.409 (4)0.7516 (19)0.6095 (7)0.092 (6)
C130.339 (4)0.761 (2)0.6491 (7)0.085 (5)
H130.19720.71010.65620.102*
C140.452 (3)0.8386 (18)0.6824 (4)0.062 (4)
H140.38260.84400.71020.074*
C150.369 (5)0.644 (2)0.5396 (6)0.131 (9)
H15A0.33450.53900.53080.196*
H15B0.53970.65690.54220.196*
H15C0.30820.71420.51780.196*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N0.180 (19)0.084 (10)0.040 (8)0.017 (14)0.005 (11)0.013 (8)
S0.060 (2)0.064 (2)0.081 (3)0.002 (2)0.005 (2)0.001 (2)
O10.065 (6)0.034 (4)0.070 (6)0.011 (5)0.005 (5)0.007 (4)
O20.105 (9)0.074 (6)0.046 (5)0.027 (7)0.018 (6)0.015 (5)
O30.148 (13)0.116 (9)0.104 (10)0.018 (12)0.024 (10)0.028 (9)
O40.34 (3)0.095 (10)0.071 (9)0.075 (16)0.019 (13)0.017 (8)
O50.138 (13)0.174 (16)0.087 (10)0.022 (12)0.016 (10)0.045 (11)
C10.062 (10)0.093 (10)0.054 (8)0.020 (10)0.011 (8)0.001 (7)
C20.055 (8)0.045 (6)0.039 (7)0.006 (7)0.002 (6)0.001 (6)
C30.050 (8)0.032 (6)0.056 (8)0.001 (7)0.005 (7)0.012 (6)
C40.067 (9)0.045 (6)0.043 (7)0.008 (7)0.003 (7)0.015 (6)
C50.082 (12)0.061 (9)0.081 (11)0.023 (10)0.014 (10)0.001 (8)
C60.078 (11)0.052 (7)0.052 (9)0.013 (9)0.009 (8)0.002 (7)
C70.067 (10)0.087 (10)0.047 (8)0.027 (10)0.019 (7)0.011 (8)
C80.057 (10)0.058 (8)0.062 (9)0.007 (8)0.007 (7)0.000 (7)
C90.049 (9)0.051 (7)0.075 (10)0.001 (8)0.025 (8)0.001 (7)
C100.052 (9)0.087 (11)0.091 (13)0.011 (9)0.005 (9)0.023 (10)
C110.103 (14)0.123 (15)0.029 (7)0.063 (14)0.001 (8)0.003 (9)
C120.113 (18)0.062 (10)0.102 (16)0.008 (12)0.020 (15)0.037 (10)
C130.070 (11)0.075 (10)0.111 (15)0.004 (11)0.019 (12)0.002 (11)
C140.060 (9)0.085 (10)0.040 (7)0.021 (9)0.009 (7)0.000 (8)
C150.19 (3)0.124 (16)0.081 (13)0.04 (2)0.008 (16)0.039 (12)
Geometric parameters (Å, º) top
N—O41.15 (3)C3—C41.418 (19)
N—O51.22 (2)C4—C51.477 (19)
N—C61.51 (2)C5—C61.36 (2)
S—O11.509 (8)C6—C71.318 (19)
S—C11.726 (14)C7—C81.400 (18)
S—C91.799 (13)C9—C141.35 (2)
O2—C21.214 (14)C9—C101.42 (2)
O3—C121.38 (2)C10—C111.39 (2)
O3—C151.42 (2)C11—C121.37 (3)
C1—C21.446 (18)C12—C131.26 (2)
C2—C31.511 (16)C13—C141.37 (2)
C3—C81.394 (17)
O4—N—O5126.9 (18)C7—C6—C5124.3 (14)
O4—N—C6123.0 (18)C7—C6—N124.3 (15)
O5—N—C6110.0 (19)C5—C6—N111.2 (15)
O1—S—C1107.1 (6)C6—C7—C8119.5 (14)
O1—S—C9107.4 (6)C3—C8—C7119.6 (13)
C1—S—C999.7 (7)C14—C9—C10118.4 (13)
C12—O3—C15113 (2)C14—C9—S126.1 (13)
C2—C1—S113.6 (11)C10—C9—S115.6 (12)
O2—C2—C1121.3 (12)C11—C10—C9117.3 (15)
O2—C2—C3119.7 (12)C12—C11—C10121.9 (15)
C1—C2—C3118.9 (12)C13—C12—C11116.8 (19)
C8—C3—C4122.4 (12)C13—C12—O3117 (2)
C8—C3—C2117.9 (12)C11—C12—O3126 (2)
C4—C3—C2119.6 (11)C12—C13—C14127 (2)
C3—C4—C5114.3 (13)C9—C14—C13118.9 (15)
C6—C5—C4119.8 (16)
(3) top
Crystal data top
C15H13NO5SZ = 2
Mr = 319.32F(000) = 332
Triclinic, P1Dx = 1.463 Mg m3
a = 6.7468 (8) ÅMo Kα radiation, λ = 0.71073 Å
b = 7.4303 (7) ÅCell parameters from 25 reflections
c = 15.201 (2) Åθ = 8.1–17.2°
α = 85.25 (1)°µ = 0.25 mm1
β = 79.56 (1)°T = 293 K
γ = 75.39 (1)°Irregular, colorless
V = 724.64 (15) Å30.25 × 0.15 × 0.10 mm
Data collection top
Enraf-Nonius CAD-4
diffractometer
Rint = 0.010
Radiation source: fine-focus sealed tubeθmax = 26.3°
Graphite monochromatorh = 08
ω/2θ scansk = 89
3188 measured reflectionsl = 1818
2930 independent reflections3 standard reflections every 60 min
2503 reflections with F2 > 2σF2 intensity decay: 1.1%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113H-atom parameters constrained
S = 1.08Calculated w = 1/[σ2(Fo2) + (0.0648)2 + 0.2154P]
where P = (Fo2 + 2Fc2)/3
2930 reflections(Δ/σ)max = 0.001
200 parametersΔρmax = 0.26 e Å3
0 restraintsΔρmin = 0.32 e Å3
Special details top

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 on F2 for ALL reflections except for 0 with very negative F2 or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating _R_factor_obs 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S0.27961 (7)0.03749 (6)0.72076 (3)0.04792 (17)
N0.1777 (3)0.3389 (3)0.41670 (14)0.0663 (5)
O10.5029 (2)0.0020 (3)0.68241 (11)0.0729 (5)
O20.3268 (3)0.0770 (2)0.90668 (11)0.0785 (5)
O30.8947 (3)0.6315 (2)0.90885 (12)0.0719 (4)
O40.3630 (4)0.3586 (4)0.42814 (16)0.1173 (8)
O50.0789 (4)0.3722 (3)0.34593 (13)0.1019 (7)
C10.2257 (4)0.2501 (3)0.77881 (15)0.0603 (5)
H1A0.26920.34680.73880.072*
H1B0.07800.29170.80070.072*
C20.3458 (3)0.2104 (3)0.85678 (13)0.0550 (5)
C30.4851 (3)0.3283 (3)0.86721 (12)0.0476 (4)
C40.4971 (3)0.4898 (3)0.81539 (13)0.0558 (5)
H40.41320.52690.77170.067*
C50.6301 (3)0.5965 (3)0.82717 (14)0.0567 (5)
H50.63510.70440.79210.068*
C60.7561 (3)0.5404 (3)0.89194 (13)0.0528 (5)
C70.7472 (3)0.3787 (3)0.94424 (13)0.0541 (5)
H70.83300.34070.98720.065*
C80.6131 (3)0.2759 (3)0.93273 (12)0.0501 (4)
H80.60640.16950.96880.060*
C90.1390 (3)0.1368 (2)0.63123 (12)0.0433 (4)
C140.0751 (3)0.1755 (3)0.64562 (14)0.0627 (6)
H140.14860.15510.70200.075*
C110.1454 (3)0.2315 (3)0.47734 (14)0.0572 (5)
H110.21810.24990.42060.069*
C100.2488 (3)0.1641 (3)0.54825 (13)0.0547 (5)
H100.39310.13720.53970.066*
C120.0672 (3)0.2704 (2)0.49281 (13)0.0488 (4)
C130.1786 (3)0.2450 (4)0.57483 (16)0.0660 (6)
H130.32300.27400.58320.079*
C150.8947 (5)0.8086 (4)0.8655 (2)0.0828 (7)
H15A0.98510.86500.88990.124*
H15B0.75630.88670.87490.124*
H15C0.94290.79360.80250.124*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S0.0442 (3)0.0493 (3)0.0518 (3)0.01112 (19)0.01421 (19)0.00199 (19)
N0.0830 (14)0.0566 (10)0.0637 (12)0.0103 (9)0.0343 (10)0.0001 (9)
O10.0408 (8)0.0987 (12)0.0659 (9)0.0099 (7)0.0102 (7)0.0072 (8)
O20.1028 (14)0.0787 (11)0.0711 (10)0.0418 (10)0.0421 (10)0.0222 (9)
O30.0641 (10)0.0681 (10)0.0894 (12)0.0236 (8)0.0240 (8)0.0108 (8)
O40.0794 (14)0.178 (2)0.1032 (16)0.0265 (14)0.0564 (12)0.0233 (15)
O50.1155 (17)0.1189 (17)0.0624 (11)0.0096 (13)0.0299 (11)0.0233 (11)
C10.0657 (13)0.0553 (11)0.0587 (12)0.0016 (9)0.0278 (10)0.0078 (9)
C20.0614 (12)0.0553 (11)0.0465 (10)0.0048 (9)0.0185 (9)0.0002 (8)
C30.0504 (10)0.0494 (10)0.0388 (9)0.0026 (8)0.0110 (7)0.0004 (7)
C40.0598 (12)0.0560 (11)0.0469 (10)0.0021 (9)0.0176 (9)0.0069 (8)
C50.0593 (12)0.0507 (11)0.0551 (11)0.0072 (9)0.0106 (9)0.0098 (9)
C60.0447 (10)0.0532 (11)0.0549 (11)0.0041 (8)0.0050 (8)0.0017 (8)
C70.0500 (10)0.0566 (11)0.0523 (11)0.0030 (8)0.0167 (8)0.0035 (8)
C80.0555 (11)0.0471 (10)0.0433 (9)0.0035 (8)0.0123 (8)0.0042 (8)
C90.0392 (9)0.0466 (9)0.0474 (9)0.0129 (7)0.0114 (7)0.0027 (7)
C140.0417 (10)0.0967 (17)0.0527 (11)0.0251 (10)0.0096 (8)0.0096 (11)
C110.0567 (12)0.0659 (12)0.0451 (10)0.0104 (9)0.0037 (8)0.0036 (9)
C100.0407 (9)0.0679 (12)0.0522 (11)0.0072 (9)0.0058 (8)0.0056 (9)
C120.0558 (11)0.0429 (9)0.0524 (10)0.0112 (8)0.0214 (8)0.0028 (8)
C130.0401 (10)0.0948 (17)0.0666 (13)0.0203 (10)0.0172 (9)0.0076 (12)
C150.0938 (19)0.0726 (16)0.0894 (18)0.0364 (14)0.0161 (15)0.0081 (14)
Geometric parameters (Å, º) top
S—O11.4771 (15)C3—C81.403 (3)
S—C11.798 (2)C4—C51.381 (3)
S—C91.8015 (18)C5—C61.386 (3)
N—O51.201 (3)C6—C71.393 (3)
N—O41.204 (3)C7—C81.364 (3)
N—C121.475 (2)C9—C101.370 (3)
O2—C21.216 (3)C9—C141.380 (3)
O3—C61.354 (3)C14—C131.382 (3)
O3—C151.422 (3)C11—C121.369 (3)
C1—C21.522 (3)C11—C101.381 (3)
C2—C31.473 (3)C12—C131.360 (3)
C3—C41.392 (3)
O1—S—C1105.67 (11)O3—C6—C5124.57 (19)
O1—S—C9106.95 (9)O3—C6—C7115.35 (18)
C1—S—C995.70 (9)C5—C6—C7120.07 (19)
O5—N—O4122.8 (2)C8—C7—C6120.25 (18)
O5—N—C12118.6 (2)C7—C8—C3120.94 (18)
O4—N—C12118.6 (2)C10—C9—C14121.07 (17)
C6—O3—C15118.26 (19)C10—C9—S118.74 (14)
C2—C1—S107.41 (14)C14—C9—S120.11 (15)
O2—C2—C3122.57 (18)C9—C14—C13118.86 (19)
O2—C2—C1117.81 (19)C12—C11—C10118.23 (18)
C3—C2—C1119.58 (17)C9—C10—C11120.02 (18)
C4—C3—C8117.88 (18)C13—C12—C11122.49 (18)
C4—C3—C2123.52 (17)C13—C12—N119.23 (19)
C8—C3—C2118.60 (17)C11—C12—N118.27 (19)
C5—C4—C3121.75 (18)C12—C13—C14119.32 (19)
C4—C5—C6119.09 (18)
 

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