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The title compound, C15H14O3S, displays a stair-like arrangement, with the tolyl and phenyl rings forming the steps. The S atom lies in the plane of the tolyl ring, whereas the ketone group CO(CH2) is coplanar with the phenyl ring.
Supporting information
CCDC reference: 235896
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.045
- wR factor = 0.104
- Data-to-parameter ratio = 10.1
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.95
Alert level C
PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low .... 0.94
PLAT380_ALERT_4_C Incorrectly Oriented X(sp2)-Methyl Moiety ...... C15
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
2 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
0 ALERT type 2 Indicator that the structure model may be wrong or deficient
2 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: PROCESS-AUTO (Rigaku, 2004); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: CRYSTALS (Watkin et al., 1996); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: CrystalStructure.
1-Phenyl-2-(toluene-4-sulfonyl)ethanone
top
Crystal data top
C15H14O3S | F(000) = 576.00 |
Mr = 274.33 | Dx = 1.346 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.7107 Å |
Hall symbol: -P 2ybc | Cell parameters from 9916 reflections |
a = 15.8077 (7) Å | θ = 1.7–27.3° |
b = 5.4113 (2) Å | µ = 0.24 mm−1 |
c = 15.8940 (9) Å | T = 293 K |
β = 95.343 (2)° | Chunk, colourless |
V = 1353.7 (1) Å3 | 0.40 × 0.24 × 0.14 mm |
Z = 4 | |
Data collection top
Rigaku R-AXIS RAPID diffractometer | 1729 reflections with F2 > 2σ(F2) |
Detector resolution: 10.00 pixels mm-1 | Rint = 0.035 |
ω scans | θmax = 27.3° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −20→20 |
Tmin = 0.862, Tmax = 0.967 | k = −6→6 |
10775 measured reflections | l = −20→20 |
2861 independent reflections | |
Refinement top
Refinement on F2 | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.045 | w = 1/[σ2(F*) + (0.0644P)2 + 0.233P] where P = 0.333max(Fo2,0) + 0.667Fc2 |
wR(F2) = 0.104 | (Δ/σ)max = 0.0003 |
S = 1.01 | Δρmax = 0.17 e Å−3 |
1730 reflections | Δρmin = −0.26 e Å−3 |
172 parameters | |
Special details top
Refinement. Refinement using reflections with F2 > 2.0 σ(F2). The
weighted R-factor (wR) and goodness of fit (S) are based
on F2. R-factor (gt) are based on F. The threshold
expression of F2 > 2.0 σ(F2) is used only for calculating
R-factor (gt). |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
S1 | 0.27957 (4) | 0.81402 (14) | 0.39622 (4) | 0.0590 | |
O1 | 0.07615 (15) | 0.6611 (4) | 0.41481 (14) | 0.0875 | |
O2 | 0.26681 (15) | 0.5529 (4) | 0.39131 (15) | 0.0880 | |
O3 | 0.32615 (12) | 0.9155 (4) | 0.46984 (11) | 0.0808 | |
C1 | 0.17732 (16) | 0.9554 (5) | 0.38419 (15) | 0.0538 | |
H1A | 0.18261 | 1.1300 | 0.39749 | 0.0500* | |
H1B | 0.1533 | 0.9395 | 0.3262 | 0.0500* | |
C2 | 0.11915 (17) | 0.8326 (5) | 0.44272 (17) | 0.0575 | |
C3 | 0.11789 (15) | 0.9178 (5) | 0.53130 (16) | 0.0500 | |
C4 | 0.16240 (18) | 1.1226 (5) | 0.56344 (18) | 0.0615 | |
H4 | 0.19491 | 1.2140 | 0.52879 | 0.0500* | |
C5 | 0.15893 (19) | 1.1908 (6) | 0.64633 (19) | 0.0686 | |
H5 | 0.18900 | 1.3286 | 0.66743 | 0.0500* | |
C6 | 0.11144 (19) | 1.0573 (7) | 0.69779 (19) | 0.0721 | |
H6 | 0.10916 | 1.1048 | 0.75377 | 0.0500* | |
C7 | 0.06723 (18) | 0.8539 (6) | 0.66705 (19) | 0.0701 | |
H7 | 0.03536 | 0.7623 | 0.70224 | 0.0500* | |
C8 | 0.07002 (17) | 0.7850 (6) | 0.58410 (18) | 0.0621 | |
H8 | 0.03938 | 0.6479 | 0.56322 | 0.0500* | |
C9 | 0.32716 (16) | 0.9122 (5) | 0.30642 (15) | 0.0498 | |
C10 | 0.31451 (18) | 0.7786 (5) | 0.23290 (17) | 0.0626 | |
H10 | 0.28115 | 0.6367 | 0.23069 | 0.0500* | |
C11 | 0.35141 (18) | 0.8567 (6) | 0.16250 (17) | 0.0670 | |
H11 | 0.34255 | 0.7665 | 0.11264 | 0.0500* | |
C12 | 0.40109 (17) | 1.0642 (6) | 0.16441 (17) | 0.0609 | |
C13 | 0.41287 (18) | 1.1956 (5) | 0.23909 (19) | 0.0653 | |
H13 | 0.44611 | 1.3377 | 0.24125 | 0.0500* | |
C14 | 0.37657 (17) | 1.1210 (5) | 0.31043 (17) | 0.0585 | |
H14 | 0.38546 | 1.2106 | 0.36042 | 0.0500* | |
C15 | 0.4428 (2) | 1.1482 (7) | 0.0880 (2) | 0.0948 | |
H151 | 0.4282 | 1.0375 | 0.0417 | 0.1118* | |
H152 | 0.5033 | 1.1492 | 0.1011 | 0.1118* | |
H153 | 0.4237 | 1.3119 | 0.0726 | 0.1118* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0700 (5) | 0.0605 (4) | 0.0476 (4) | 0.0075 (4) | 0.0116 (3) | 0.0113 (3) |
O1 | 0.0995 (16) | 0.0955 (18) | 0.0698 (14) | −0.0434 (14) | 0.0206 (11) | −0.0196 (12) |
O2 | 0.1153 (17) | 0.0499 (12) | 0.1051 (18) | 0.0137 (12) | 0.0435 (14) | 0.0200 (12) |
O3 | 0.0771 (13) | 0.1228 (18) | 0.0412 (11) | 0.0040 (13) | −0.0014 (9) | 0.0091 (12) |
C1 | 0.0664 (16) | 0.0533 (16) | 0.0416 (14) | 0.0003 (13) | 0.0041 (12) | 0.0042 (12) |
C2 | 0.0610 (16) | 0.0576 (17) | 0.0547 (16) | −0.0057 (15) | 0.0091 (12) | 0.0010 (14) |
C3 | 0.0519 (14) | 0.0506 (14) | 0.0484 (15) | 0.0015 (13) | 0.0088 (11) | 0.0030 (12) |
C4 | 0.0724 (18) | 0.0533 (17) | 0.0609 (18) | −0.0043 (14) | 0.0169 (14) | 0.0000 (13) |
C5 | 0.0785 (19) | 0.0615 (18) | 0.0659 (19) | 0.0020 (16) | 0.0077 (15) | −0.0157 (16) |
C6 | 0.0710 (19) | 0.096 (2) | 0.0508 (17) | 0.0178 (19) | 0.0140 (14) | −0.0086 (18) |
C7 | 0.0642 (18) | 0.092 (2) | 0.0568 (18) | −0.0002 (17) | 0.0203 (14) | 0.0104 (17) |
C8 | 0.0575 (15) | 0.0673 (18) | 0.0622 (17) | −0.0087 (14) | 0.0100 (13) | 0.0038 (15) |
C9 | 0.0557 (14) | 0.0514 (14) | 0.0425 (14) | 0.0024 (13) | 0.0063 (11) | −0.0006 (12) |
C10 | 0.0682 (17) | 0.0635 (17) | 0.0564 (17) | −0.0107 (15) | 0.0072 (13) | −0.0112 (14) |
C11 | 0.0743 (18) | 0.083 (2) | 0.0442 (16) | 0.0021 (17) | 0.0057 (13) | −0.0151 (15) |
C12 | 0.0555 (16) | 0.079 (2) | 0.0496 (16) | 0.0121 (16) | 0.0113 (12) | 0.0071 (15) |
C13 | 0.0657 (17) | 0.0612 (17) | 0.071 (2) | −0.0108 (15) | 0.0157 (14) | 0.0000 (16) |
C14 | 0.0699 (17) | 0.0575 (17) | 0.0487 (15) | −0.0008 (14) | 0.0090 (13) | −0.0106 (13) |
C15 | 0.087 (2) | 0.137 (3) | 0.064 (2) | 0.011 (2) | 0.0288 (17) | 0.020 (2) |
Geometric parameters (Å, º) top
S1—O2 | 1.428 (2) | C7—H7 | 0.930 |
S1—O3 | 1.433 (2) | C7—C8 | 1.375 (4) |
S1—C1 | 1.782 (3) | C8—H8 | 0.930 |
S1—C9 | 1.756 (3) | C9—C10 | 1.373 (4) |
O1—C2 | 1.210 (3) | C9—C14 | 1.372 (3) |
C1—H1A | 0.970 | C10—H10 | 0.930 |
C1—H1B | 0.968 | C10—C11 | 1.376 (4) |
C1—C2 | 1.520 (3) | C11—H11 | 0.930 |
C2—C3 | 1.483 (4) | C11—C12 | 1.369 (4) |
C3—C4 | 1.385 (4) | C12—C13 | 1.381 (4) |
C3—C8 | 1.383 (3) | C12—C15 | 1.505 (4) |
C4—H4 | 0.930 | C13—H13 | 0.930 |
C4—C5 | 1.374 (4) | C13—C14 | 1.378 (4) |
C5—H5 | 0.930 | C14—H14 | 0.930 |
C5—C6 | 1.367 (4) | C15—H151 | 0.960 |
C6—H6 | 0.930 | C15—H152 | 0.960 |
C6—C7 | 1.369 (4) | C15—H153 | 0.960 |
| | | |
O2—S1—O3 | 118.87 (14) | H7—C7—C8 | 119.960 |
O2—S1—C1 | 107.26 (13) | C3—C8—C7 | 120.6 (3) |
O3—S1—C1 | 108.37 (13) | C3—C8—H8 | 119.624 |
O2—S1—C9 | 108.90 (13) | C7—C8—H8 | 119.773 |
O3—S1—C9 | 108.75 (13) | S1—C9—C10 | 119.5 (2) |
C1—S1—C9 | 103.63 (12) | S1—C9—C14 | 119.8 (2) |
S1—C1—H1A | 109.620 | C10—C9—C14 | 120.7 (3) |
S1—C1—H1B | 109.641 | C9—C10—H10 | 120.267 |
H1A—C1—H1B | 108.188 | C9—C10—C11 | 119.4 (3) |
S1—C1—C2 | 109.94 (18) | H10—C10—C11 | 120.311 |
H1A—C1—C2 | 109.688 | C10—C11—H11 | 119.359 |
H1B—C1—C2 | 109.739 | C10—C11—C12 | 121.3 (3) |
C1—C2—O1 | 117.5 (2) | H11—C11—C12 | 119.324 |
C1—C2—C3 | 120.5 (2) | C11—C12—C13 | 118.2 (3) |
O1—C2—C3 | 122.0 (2) | C11—C12—C15 | 121.5 (3) |
C2—C3—C4 | 123.2 (2) | C13—C12—C15 | 120.3 (3) |
C2—C3—C8 | 118.1 (2) | C12—C13—H13 | 119.186 |
C4—C3—C8 | 118.7 (2) | C12—C13—C14 | 121.5 (3) |
C3—C4—H4 | 119.816 | H13—C13—C14 | 119.272 |
C3—C4—C5 | 120.3 (3) | C13—C14—C9 | 118.8 (3) |
H4—C4—C5 | 119.906 | C13—C14—H14 | 120.593 |
C4—C5—H5 | 119.749 | C9—C14—H14 | 120.594 |
C4—C5—C6 | 120.3 (3) | C12—C15—H151 | 109.747 |
H5—C5—C6 | 119.912 | C12—C15—H152 | 109.192 |
C5—C6—H6 | 119.938 | H151—C15—H152 | 109.476 |
C5—C6—C7 | 120.1 (3) | C12—C15—H153 | 109.461 |
H6—C6—C7 | 119.954 | H151—C15—H153 | 109.476 |
C6—C7—H7 | 120.071 | H152—C15—H153 | 109.476 |
C6—C7—C8 | 120.0 (3) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8···O1i | 0.93 | 2.52 | 3.341 (3) | 147 |
C11—H11···O3ii | 0.93 | 2.46 | 3.388 (3) | 171 |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) x, −y+3/2, z−1/2. |
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