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The asymmetric unit of the title compound, C10H12O3S, contains two independent mol­ecules having different conformations. In one conformation, the aromatic ring and the acetyl substituent are gauche to each other, while in the other they are anti.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806047635/sa2024sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806047635/sa2024Isup2.hkl
Contains datablock I

CCDC reference: 630448

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.039
  • wR factor = 0.104
  • Data-to-parameter ratio = 17.1

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.59 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C2 PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 5
Alert level G REFLT03_ALERT_4_G WARNING: Large fraction of Friedel related reflns may be needed to determine absolute structure From the CIF: _diffrn_reflns_theta_max 28.32 From the CIF: _reflns_number_total 4419 Count of symmetry unique reflns 2952 Completeness (_total/calc) 149.70% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1467 Fraction of Friedel pairs measured 0.497 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART-NT (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1999); data reduction: XPREP (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); 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 (Farrugia, 1999) and PLATON (Spek, 2003).

1-(p-Tolylsulfonyl)propan-2-one top
Crystal data top
C10H12O3SF(000) = 448
Mr = 212.26Dx = 1.315 Mg m3
Monoclinic, P21Melting point = 323–324 K
Hall symbol: P 2ybMo Kα radiation, λ = 0.71073 Å
a = 14.5381 (16) ÅCell parameters from 863 reflections
b = 5.5394 (6) Åθ = 2.8–26.3°
c = 14.6879 (16) ŵ = 0.28 mm1
β = 114.998 (2)°T = 294 K
V = 1072.0 (2) Å3Cut_plate, colourless
Z = 40.4 × 0.4 × 0.12 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
4419 independent reflections
Radiation source: fine-focus sealed tube3580 reflections with I > 2σ(I))
Graphite monochromatorRint = 0.019
φ and ω scansθmax = 28.3°, θmin = 1.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1919
Tmin = 0.891, Tmax = 0.967k = 67
7547 measured reflectionsl = 1819
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)] = 0.039H-atom parameters constrained
wR(F2) = 0.104 w = 1/[σ2(Fo2) + (0.0638P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.024
4419 reflectionsΔρmax = 0.21 e Å3
258 parametersΔρmin = 0.23 e Å3
1 restraintAbsolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.03 (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 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C1'0.0227 (2)0.1556 (6)0.3375 (2)0.0588 (7)
H1A'0.09310.1270.29510.088*
H1B'0.01570.30440.37330.088*
H1C'0.01440.16570.29690.088*
C10.3376 (3)0.7743 (6)0.7593 (3)0.0865 (11)
H1A0.30210.77640.68740.13*
H1B0.31180.64560.78570.13*
H1C0.40870.74970.77830.13*
C2'0.01799 (18)0.0464 (5)0.41036 (18)0.0444 (6)
C20.3223 (2)1.0084 (6)0.8003 (2)0.0542 (7)
C30.38441 (18)1.0602 (5)0.9114 (2)0.0536 (7)
H3A0.38031.23160.92270.064*
H3B0.45491.02280.92820.064*
C3'0.13032 (17)0.0319 (5)0.48208 (18)0.0444 (6)
H3A'0.15170.13560.49170.053*
H3B'0.14070.09810.54690.053*
C40.21677 (16)0.9638 (5)0.95378 (17)0.0438 (6)
C4'0.32989 (16)0.1296 (4)0.51877 (17)0.0395 (5)
C5'0.37936 (19)0.2816 (5)0.59877 (19)0.0528 (6)
H5'0.34670.41880.60690.063*
C50.1866 (2)1.1690 (6)0.9861 (2)0.0620 (7)
H50.23461.27261.03120.074*
C60.0838 (2)1.2206 (7)0.9508 (2)0.0661 (8)
H60.06341.35940.97290.079*
C6'0.47698 (19)0.2310 (6)0.6669 (2)0.0597 (7)
H6'0.51070.3360.720.072*
C70.0119 (2)1.0704 (6)0.8842 (2)0.0544 (7)
C7'0.5252 (2)0.0240 (6)0.6564 (2)0.0578 (7)
C80.04351 (19)0.8679 (7)0.8522 (2)0.0633 (8)
H80.00470.7650.80690.076*
C8'0.47466 (19)0.1272 (6)0.5757 (2)0.0572 (7)
H8'0.5070.26480.56750.069*
C9'0.37663 (17)0.0766 (5)0.50709 (18)0.0491 (6)
H9'0.34270.18070.45370.059*
C90.14605 (19)0.8120 (6)0.8859 (2)0.0575 (7)
H90.16630.67460.86290.069*
C10'0.6324 (2)0.0330 (10)0.7325 (3)0.1022 (15)
H10D0.66780.11780.69990.153*
H10E0.62980.13180.7850.153*
H10F0.66750.11460.76070.153*
C100.1003 (2)1.1317 (8)0.8439 (3)0.0798 (11)
H10A0.11261.22080.89380.12*
H10B0.13930.98540.82840.12*
H10C0.11981.22770.78420.12*
O10.26371 (16)1.1560 (5)0.74856 (16)0.0747 (6)
O1'0.03263 (15)0.2135 (4)0.41460 (16)0.0716 (6)
O20.35770 (15)0.6445 (4)0.98151 (16)0.0655 (5)
O2'0.18700 (14)0.0951 (4)0.33745 (13)0.0659 (6)
O30.40167 (15)1.0012 (5)1.09230 (15)0.0760 (7)
O3'0.18760 (15)0.4497 (4)0.43782 (18)0.0766 (6)
S1'0.20456 (4)0.19591 (12)0.43282 (4)0.04616 (16)
S10.34665 (4)0.89814 (12)0.99473 (5)0.05059 (18)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C1'0.0496 (14)0.062 (2)0.0575 (15)0.0103 (13)0.0159 (12)0.0087 (14)
C10.131 (3)0.059 (2)0.083 (2)0.011 (2)0.059 (2)0.0015 (18)
C2'0.0385 (12)0.0471 (16)0.0471 (13)0.0013 (11)0.0175 (10)0.0038 (11)
C20.0502 (14)0.0547 (17)0.0636 (17)0.0007 (13)0.0297 (13)0.0049 (13)
C30.0365 (12)0.0479 (17)0.0705 (17)0.0033 (11)0.0169 (12)0.0025 (13)
C3'0.0397 (12)0.0441 (15)0.0482 (13)0.0013 (10)0.0173 (10)0.0020 (10)
C40.0360 (11)0.0506 (16)0.0394 (11)0.0004 (10)0.0107 (9)0.0006 (10)
C4'0.0349 (10)0.0378 (13)0.0455 (12)0.0010 (9)0.0166 (9)0.0016 (10)
C5'0.0498 (14)0.0469 (16)0.0582 (15)0.0015 (12)0.0193 (12)0.0096 (12)
C50.0510 (14)0.064 (2)0.0613 (15)0.0018 (14)0.0144 (12)0.0203 (15)
C60.0570 (15)0.071 (2)0.0715 (17)0.0096 (15)0.0280 (13)0.0133 (16)
C6'0.0483 (13)0.067 (2)0.0519 (14)0.0082 (14)0.0100 (11)0.0122 (14)
C70.0421 (13)0.075 (2)0.0470 (14)0.0053 (13)0.0197 (11)0.0139 (13)
C7'0.0406 (13)0.077 (2)0.0547 (16)0.0015 (13)0.0188 (12)0.0125 (14)
C80.0425 (13)0.072 (2)0.0621 (16)0.0100 (14)0.0096 (12)0.0118 (15)
C8'0.0489 (14)0.0548 (18)0.0742 (17)0.0160 (13)0.0322 (13)0.0080 (14)
C9'0.0466 (12)0.0459 (16)0.0549 (14)0.0014 (12)0.0214 (11)0.0057 (12)
C90.0487 (14)0.0539 (17)0.0646 (17)0.0047 (12)0.0188 (13)0.0141 (13)
C10'0.0451 (16)0.158 (4)0.084 (2)0.018 (2)0.0083 (16)0.019 (3)
C100.0467 (15)0.116 (3)0.0740 (19)0.0150 (17)0.0233 (14)0.023 (2)
O10.0660 (12)0.0800 (17)0.0691 (13)0.0181 (12)0.0198 (10)0.0141 (12)
O1'0.0579 (11)0.0638 (14)0.0895 (14)0.0189 (11)0.0276 (10)0.0040 (12)
O20.0597 (12)0.0478 (13)0.0849 (13)0.0135 (9)0.0266 (10)0.0153 (10)
O2'0.0560 (11)0.0958 (18)0.0405 (10)0.0115 (11)0.0152 (8)0.0044 (9)
O30.0561 (11)0.0981 (19)0.0495 (11)0.0014 (11)0.0012 (9)0.0049 (11)
O3'0.0542 (11)0.0406 (13)0.1173 (18)0.0062 (9)0.0191 (11)0.0189 (12)
S1'0.0372 (3)0.0433 (4)0.0520 (3)0.0001 (3)0.0130 (2)0.0085 (3)
S10.0391 (3)0.0534 (4)0.0478 (3)0.0041 (3)0.0073 (2)0.0039 (3)
Geometric parameters (Å, º) top
C1'—C2'1.487 (4)C5—C61.389 (4)
C1'—H1A'0.96C5—H50.93
C1'—H1B'0.96C6—C71.371 (4)
C1'—H1C'0.96C6—H60.93
C1—C21.485 (4)C6'—C7'1.386 (4)
C1—H1A0.96C6'—H6'0.93
C1—H1B0.96C7—C81.367 (4)
C1—H1C0.96C7—C101.520 (4)
C2'—O1'1.201 (3)C7'—C8'1.381 (4)
C2'—C3'1.526 (3)C7'—C10'1.519 (4)
C2—O11.194 (3)C8—C91.393 (4)
C2—C31.522 (4)C8—H80.93
C3—S11.781 (3)C8'—C9'1.383 (3)
C3—H3A0.97C8'—H8'0.93
C3—H3B0.97C9'—H9'0.93
C3'—S1'1.782 (2)C9—H90.93
C3'—H3A'0.97C10'—H10D0.96
C3'—H3B'0.97C10'—H10E0.96
C4—C51.373 (4)C10'—H10F0.96
C4—C91.376 (4)C10—H10A0.96
C4—S11.761 (2)C10—H10B0.96
C4'—C5'1.376 (3)C10—H10C0.96
C4'—C9'1.377 (4)O2—S11.436 (2)
C4'—S1'1.762 (2)O2'—S1'1.427 (2)
C5'—C6'1.376 (4)O3—S11.432 (2)
C5'—H5'0.93O3'—S1'1.434 (2)
C2'—C1'—H1A'109.5C5'—C6'—C7'120.2 (3)
C2'—C1'—H1B'109.5C5'—C6'—H6'119.9
H1A'—C1'—H1B'109.5C7'—C6'—H6'119.9
C2'—C1'—H1C'109.5C8—C7—C6118.6 (2)
H1A'—C1'—H1C'109.5C8—C7—C10120.7 (3)
H1B'—C1'—H1C'109.5C6—C7—C10120.7 (3)
C2—C1—H1A109.5C8'—C7'—C6'119.1 (2)
C2—C1—H1B109.5C8'—C7'—C10'120.9 (3)
H1A—C1—H1B109.5C6'—C7'—C10'120.0 (3)
C2—C1—H1C109.5C7—C8—C9121.7 (3)
H1A—C1—H1C109.5C7—C8—H8119.2
H1B—C1—H1C109.5C9—C8—H8119.2
O1'—C2'—C1'123.4 (2)C7'—C8'—C9'120.9 (3)
O1'—C2'—C3'120.4 (2)C7'—C8'—H8'119.6
C1'—C2'—C3'116.2 (2)C9'—C8'—H8'119.6
O1—C2—C1121.9 (3)C4'—C9'—C8'119.2 (2)
O1—C2—C3119.6 (3)C4'—C9'—H9'120.4
C1—C2—C3118.5 (3)C8'—C9'—H9'120.4
C2—C3—S1115.20 (18)C4—C9—C8118.8 (3)
C2—C3—H3A108.5C4—C9—H9120.6
S1—C3—H3A108.5C8—C9—H9120.6
C2—C3—H3B108.5C7'—C10'—H10D109.5
S1—C3—H3B108.5C7'—C10'—H10E109.5
H3A—C3—H3B107.5H10D—C10'—H10E109.5
C2'—C3'—S1'110.37 (17)C7'—C10'—H10F109.5
C2'—C3'—H3A'109.6H10D—C10'—H10F109.5
S1'—C3'—H3A'109.6H10E—C10'—H10F109.5
C2'—C3'—H3B'109.6C7—C10—H10A109.5
S1'—C3'—H3B'109.6C7—C10—H10B109.5
H3A'—C3'—H3B'108.1H10A—C10—H10B109.5
C5—C4—C9120.4 (2)C7—C10—H10C109.5
C5—C4—S1120.44 (19)H10A—C10—H10C109.5
C9—C4—S1119.1 (2)H10B—C10—H10C109.5
C5'—C4'—C9'120.5 (2)O2'—S1'—O3'118.05 (14)
C5'—C4'—S1'119.6 (2)O2'—S1'—C4'108.88 (12)
C9'—C4'—S1'119.94 (18)O3'—S1'—C4'108.40 (12)
C4'—C5'—C6'120.2 (3)O2'—S1'—C3'108.14 (12)
C4'—C5'—H5'119.9O3'—S1'—C3'109.41 (14)
C6'—C5'—H5'119.9C4'—S1'—C3'102.90 (11)
C4—C5—C6119.5 (3)O3—S1—O2118.57 (14)
C4—C5—H5120.2O3—S1—C4108.92 (13)
C6—C5—H5120.2O2—S1—C4108.72 (13)
C7—C6—C5121.1 (3)O3—S1—C3106.41 (15)
C7—C6—H6119.5O2—S1—C3108.40 (14)
C5—C6—H6119.5C4—S1—C3104.98 (12)
O1—C2—C3—S1106.9 (3)C5—C4—C9—C81.3 (4)
C1—C2—C3—S173.8 (3)S1—C4—C9—C8178.7 (2)
O1'—C2'—C3'—S1'85.9 (3)C7—C8—C9—C40.7 (5)
C1'—C2'—C3'—S1'94.3 (2)C5'—C4'—S1'—O2'152.5 (2)
C9'—C4'—C5'—C6'1.3 (4)C9'—C4'—S1'—O2'29.2 (2)
S1'—C4'—C5'—C6'179.5 (2)C5'—C4'—S1'—O3'22.9 (2)
C9—C4—C5—C61.0 (4)C9'—C4'—S1'—O3'158.8 (2)
S1—C4—C5—C6178.4 (2)C5'—C4'—S1'—C3'92.9 (2)
C4—C5—C6—C70.1 (5)C9'—C4'—S1'—C3'85.3 (2)
C4'—C5'—C6'—C7'1.4 (4)C2'—C3'—S1'—O2'58.9 (2)
C5—C6—C7—C80.4 (5)C2'—C3'—S1'—O3'70.9 (2)
C5—C6—C7—C10178.4 (3)C2'—C3'—S1'—C4'173.97 (18)
C5'—C6'—C7'—C8'1.3 (4)C5—C4—S1—O328.8 (3)
C5'—C6'—C7'—C10'179.1 (3)C9—C4—S1—O3153.8 (2)
C6—C7—C8—C90.1 (5)C5—C4—S1—O2159.3 (2)
C10—C7—C8—C9178.1 (3)C9—C4—S1—O223.3 (3)
C6'—C7'—C8'—C9'1.2 (4)C5—C4—S1—C384.9 (2)
C10'—C7'—C8'—C9'179.3 (3)C9—C4—S1—C392.5 (2)
C5'—C4'—C9'—C8'1.2 (4)C2—C3—S1—O3170.3 (2)
S1'—C4'—C9'—C8'179.4 (2)C2—C3—S1—O261.1 (2)
C7'—C8'—C9'—C4'1.1 (4)C2—C3—S1—C454.9 (2)
 

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