1-Phenyl-2-(toluene-4-sulfonyl)­ethanone

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.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](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

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Computing details

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

Crystal data

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) Å^3	0.40 × 0.24 × 0.14 mm
Z = 4

Data collection

Rigaku R-AXIS RAPID diffractometer	1729 reflections with F^2 > 2σ(F^2)
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

Refinement on F^2	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.045	w = 1/[σ^2(F*) + (0.0644P)^2 + 0.233P] where P = 0.333max(Fo^2,0) + 0.667Fc^2
wR(F^2) = 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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O1^i	0.93	2.52	3.341 (3)	147
C11—H11···O3^ii	0.93	2.46	3.388 (3)	171

Symmetry codes: (i) −x, −y+1, −z+1; (ii) x, −y+3/2, z−1/2.