4-Acetyl­phenyl phenyl sulfone

The title compound, C₁₄H₁₂O₃S, is an important synthetic inter­mediate in organic synthesis whose derivatives show favourable antiviral activity [Tetsushi, Yuji, Hirotaka, Masaki, Katsunori & Shozo (2003). Green Chem. 6, 690-692]. The average S-C and S=O bond lengths are1.781 (3) and 1.436 (2) Å, respectively, and the two benzene planes are almost perpendicular to one another, forming a dihedral angle of 103.79 (9)°.<

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.045
• wR factor = 0.119
• Data-to-parameter ratio = 14.0

checkCIF/PLATON results

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PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?

Alert level G

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   2 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
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Computing details

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Bruker, 2002); software used to prepare material for publication: SHELXL97.

4-Acetylphenyl phenyl sulfone

Crystal data

C14H12O3S	Dx = 1.375 Mg m^−3
Mr = 260.31	Melting point: 412 K
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 5196 reflections
a = 21.300 (8) Å	θ = 2.4–26.3°
b = 7.756 (3) Å	µ = 0.25 mm^−1
c = 15.227 (6) Å	T = 298 K
V = 2515.5 (17) Å^3	Block, colourless
Z = 8	0.32 × 0.24 × 0.20 mm
F(000) = 1088

Data collection

Bruker SMART CCD area-detector diffractometer	2297 independent reflections
Radiation source: fine-focus sealed tube	2096 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
φ and ω scans	θmax = 25.3°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −25→22
Tmin = 0.923, Tmax = 0.951	k = −9→9
12493 measured reflections	l = −18→12

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.119	H-atom parameters not defined?
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0616P)^2 + 1.0763P] where P = (Fo^2 + 2Fc^2)/3
2297 reflections	(Δ/σ)max = 0.001
164 parameters	Δρmax = 0.30 e Å^−3
0 restraints	Δρmin = −0.25 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
S1	0.83181 (2)	0.37336 (7)	0.70265 (3)	0.0469 (2)
O1	0.77347 (7)	0.3295 (2)	0.66161 (11)	0.0689 (5)
O2	0.85856 (8)	0.54039 (19)	0.68886 (11)	0.0642 (5)
O3	1.01097 (9)	−0.3096 (2)	0.60659 (18)	0.0972 (8)
C1	1.09286 (11)	−0.1109 (4)	0.5909 (2)	0.0705 (7)
H1A	1.1164	−0.2115	0.5746	0.106*
H1B	1.1110	−0.0603	0.6425	0.106*
H1C	1.0939	−0.0289	0.5437	0.106*
C2	1.02674 (11)	−0.1602 (3)	0.60918 (17)	0.0579 (6)
C3	0.97895 (9)	−0.0245 (3)	0.63008 (14)	0.0465 (5)
C4	0.99313 (10)	0.1497 (3)	0.62887 (16)	0.0534 (5)
H4	1.0334	0.1849	0.6134	0.064*
C5	0.94873 (10)	0.2717 (3)	0.65013 (15)	0.0510 (5)
H5	0.9589	0.3883	0.6498	0.061*
C6	0.88905 (9)	0.2186 (3)	0.67185 (12)	0.0429 (5)
C7	0.87297 (10)	0.0450 (3)	0.67161 (15)	0.0501 (5)
H7	0.8322	0.0105	0.6847	0.060*
C8	0.91816 (10)	−0.0748 (3)	0.65174 (15)	0.0520 (5)
H8	0.9080	−0.1915	0.6528	0.062*
C9	0.82353 (8)	0.3428 (2)	0.81664 (14)	0.0397 (4)
C10	0.86769 (9)	0.4134 (3)	0.87246 (14)	0.0441 (5)
H10	0.9012	0.4764	0.8501	0.053*
C11	0.86154 (11)	0.3894 (3)	0.96176 (15)	0.0554 (6)
H11	0.8913	0.4352	0.9999	0.066*
C12	0.81146 (11)	0.2978 (3)	0.99451 (16)	0.0585 (6)
H12	0.8072	0.2829	1.0548	0.070*
C13	0.76794 (11)	0.2284 (3)	0.93862 (17)	0.0632 (6)
H13	0.7343	0.1661	0.9613	0.076*
C14	0.77337 (10)	0.2498 (3)	0.84897 (16)	0.0537 (5)
H14	0.7438	0.2025	0.8111	0.064*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0489 (3)	0.0447 (3)	0.0472 (3)	0.0046 (2)	−0.0055 (2)	0.0040 (2)
O1	0.0558 (9)	0.0851 (12)	0.0658 (10)	0.0129 (9)	−0.0218 (8)	−0.0072 (9)
O2	0.0824 (11)	0.0426 (9)	0.0676 (10)	0.0048 (8)	0.0061 (8)	0.0156 (7)
O3	0.0661 (12)	0.0538 (11)	0.172 (2)	0.0060 (9)	0.0174 (13)	−0.0097 (13)
C1	0.0494 (13)	0.0757 (17)	0.0864 (18)	0.0060 (12)	0.0069 (12)	−0.0074 (14)
C2	0.0530 (12)	0.0543 (14)	0.0665 (15)	0.0017 (11)	−0.0020 (11)	−0.0026 (11)
C3	0.0440 (11)	0.0479 (11)	0.0476 (11)	−0.0035 (9)	−0.0017 (8)	−0.0026 (9)
C4	0.0414 (11)	0.0546 (13)	0.0642 (14)	−0.0108 (10)	0.0045 (10)	−0.0017 (10)
C5	0.0514 (12)	0.0412 (10)	0.0605 (13)	−0.0087 (9)	0.0016 (10)	−0.0007 (9)
C6	0.0453 (11)	0.0443 (11)	0.0390 (10)	−0.0013 (9)	−0.0027 (8)	−0.0003 (8)
C7	0.0422 (11)	0.0477 (12)	0.0605 (13)	−0.0089 (9)	0.0055 (9)	−0.0022 (10)
C8	0.0519 (12)	0.0413 (11)	0.0628 (13)	−0.0089 (9)	0.0017 (10)	−0.0038 (10)
C9	0.0371 (10)	0.0320 (9)	0.0501 (11)	0.0031 (7)	−0.0004 (8)	−0.0003 (8)
C10	0.0385 (10)	0.0402 (10)	0.0537 (12)	−0.0015 (8)	0.0018 (8)	−0.0035 (9)
C11	0.0550 (13)	0.0588 (13)	0.0524 (13)	0.0046 (10)	−0.0052 (10)	−0.0117 (10)
C12	0.0639 (14)	0.0603 (14)	0.0513 (12)	0.0071 (12)	0.0098 (11)	0.0043 (11)
C13	0.0597 (14)	0.0570 (14)	0.0728 (16)	−0.0089 (11)	0.0169 (12)	0.0100 (12)
C14	0.0466 (11)	0.0488 (12)	0.0657 (14)	−0.0092 (10)	−0.0003 (10)	−0.0023 (10)

Geometric parameters (Å, º)

S1—O2	1.4308 (17)	C6—C7	1.390 (3)
S1—O1	1.4321 (17)	C7—C8	1.372 (3)
S1—C9	1.761 (2)	C7—H7	0.9300
S1—C6	1.774 (2)	C8—H8	0.9300
O3—C2	1.207 (3)	C9—C14	1.380 (3)
C1—C2	1.486 (3)	C9—C10	1.381 (3)
C1—H1A	0.9600	C10—C11	1.379 (3)
C1—H1B	0.9600	C10—H10	0.9300
C1—H1C	0.9600	C11—C12	1.375 (3)
C2—C3	1.498 (3)	C11—H11	0.9300
C3—C4	1.384 (3)	C12—C13	1.369 (3)
C3—C8	1.392 (3)	C12—H12	0.9300
C4—C5	1.377 (3)	C13—C14	1.380 (3)
C4—H4	0.9300	C13—H13	0.9300
C5—C6	1.376 (3)	C14—H14	0.9300
C5—H5	0.9300
O2—S1—O1	119.79 (11)	C7—C6—S1	119.14 (15)
O2—S1—C9	107.85 (10)	C8—C7—C6	118.94 (19)
O1—S1—C9	108.14 (10)	C8—C7—H7	120.5
O2—S1—C6	107.46 (10)	C6—C7—H7	120.5
O1—S1—C6	108.67 (10)	C7—C8—C3	121.0 (2)
C9—S1—C6	103.79 (9)	C7—C8—H8	119.5
C2—C1—H1A	109.5	C3—C8—H8	119.5
C2—C1—H1B	109.5	C14—C9—C10	121.0 (2)
H1A—C1—H1B	109.5	C14—C9—S1	119.97 (16)
C2—C1—H1C	109.5	C10—C9—S1	119.02 (15)
H1A—C1—H1C	109.5	C11—C10—C9	119.26 (19)
H1B—C1—H1C	109.5	C11—C10—H10	120.4
O3—C2—C1	120.3 (2)	C9—C10—H10	120.4
O3—C2—C3	119.5 (2)	C12—C11—C10	120.1 (2)
C1—C2—C3	120.2 (2)	C12—C11—H11	120.0
C4—C3—C8	118.67 (19)	C10—C11—H11	120.0
C4—C3—C2	122.30 (19)	C13—C12—C11	120.2 (2)
C8—C3—C2	119.03 (19)	C13—C12—H12	119.9
C5—C4—C3	121.18 (19)	C11—C12—H12	119.9
C5—C4—H4	119.4	C12—C13—C14	120.7 (2)
C3—C4—H4	119.4	C12—C13—H13	119.6
C6—C5—C4	119.0 (2)	C14—C13—H13	119.6
C6—C5—H5	120.5	C9—C14—C13	118.7 (2)
C4—C5—H5	120.5	C9—C14—H14	120.6
C5—C6—C7	121.13 (19)	C13—C14—H14	120.6
C5—C6—S1	119.72 (16)
O3—C2—C3—C4	−176.0 (3)	C6—C7—C8—C3	−1.5 (3)
C1—C2—C3—C4	3.4 (4)	C4—C3—C8—C7	0.0 (3)
O3—C2—C3—C8	4.2 (4)	C2—C3—C8—C7	179.8 (2)
C1—C2—C3—C8	−176.5 (2)	O2—S1—C9—C14	145.65 (17)
C8—C3—C4—C5	1.2 (4)	O1—S1—C9—C14	14.74 (19)
C2—C3—C4—C5	−178.6 (2)	C6—S1—C9—C14	−100.55 (17)
C3—C4—C5—C6	−0.8 (4)	O2—S1—C9—C10	−34.17 (18)
C4—C5—C6—C7	−0.7 (3)	O1—S1—C9—C10	−165.07 (15)
C4—C5—C6—S1	178.11 (17)	C6—S1—C9—C10	79.63 (17)
O2—S1—C6—C5	6.7 (2)	C14—C9—C10—C11	0.4 (3)
O1—S1—C6—C5	137.74 (18)	S1—C9—C10—C11	−179.81 (16)
C9—S1—C6—C5	−107.34 (18)	C9—C10—C11—C12	−0.8 (3)
O2—S1—C6—C7	−174.38 (16)	C10—C11—C12—C13	0.8 (3)
O1—S1—C6—C7	−43.38 (19)	C11—C12—C13—C14	−0.3 (4)
C9—S1—C6—C7	71.54 (18)	C10—C9—C14—C13	0.0 (3)
C5—C6—C7—C8	1.9 (3)	S1—C9—C14—C13	−179.78 (17)
S1—C6—C7—C8	−176.98 (16)	C12—C13—C14—C9	−0.1 (4)