2-(4-Methyl­phenyl­sulfon­yl)-1,3-diphenyl­prop-2-en-1-one

In the title compound, C₂₂H₁₈O₃S, the phen­yl group and sulfon­yl substituent are trans with respect to the olefinic bond.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.045
• wR factor = 0.141
• Data-to-parameter ratio = 17.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C7
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C19

   0 ALERT level A = In general: serious problem
   0 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
   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
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 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.

2-(4-Methylphenylsulfonyl)-1,3-diphenylprop-2-en-1-one

Crystal data

C22H18O3S	F(000) = 760.00
Mr = 362.44	Dx = 1.279 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: -P 2yn	Cell parameters from 12090 reflections
a = 13.6890 (4) Å	θ = 2.5–27.4°
b = 8.2386 (2) Å	µ = 0.19 mm^−1
c = 16.7066 (5) Å	T = 296 K
β = 92.9198 (9)°	Block, colorless
V = 1881.69 (9) Å^3	0.60 × 0.40 × 0.20 mm
Z = 4

Data collection

Rigaku R-AXIS RAPID diffractometer	3067 reflections with F^2 > 2σ(F^2)
Detector resolution: 10.00 pixels mm^-1	Rint = 0.025
ω scans	θmax = 27.4°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −17→17
Tmin = 0.827, Tmax = 0.963	k = −10→10
18258 measured reflections	l = −21→21
4301 independent reflections

Refinement

Refinement on F^2	w = 1/[0.0024Fo^2 + σ(Fo^2)]/(4Fo^2)
R[F^2 > 2σ(F^2)] = 0.045	(Δ/σ)max < 0.001
wR(F^2) = 0.141	Δρmax = 0.29 e Å^−3
S = 1.00	Δρmin = −0.28 e Å^−3
4116 reflections	Extinction correction: Larson (1970)
236 parameters	Extinction coefficient: 124 (37)
H-atom parameters constrained

Special details

Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY

Refinement. Refinement using all reflections. 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	0.67670 (3)	0.46093 (5)	0.84053 (3)	0.0479 (1)
O1	0.4345 (1)	0.4160 (2)	0.8205 (1)	0.0884 (6)
O2	0.76991 (9)	0.4379 (2)	0.80708 (8)	0.0634 (4)
O3	0.6593 (1)	0.6096 (1)	0.88222 (9)	0.0680 (4)
C1	0.5857 (1)	0.4447 (2)	0.7617 (1)	0.0449 (4)
C2	0.6102 (1)	0.3744 (2)	0.6938 (1)	0.0479 (5)
C3	0.5507 (1)	0.3365 (2)	0.6207 (1)	0.0519 (5)
C4	0.4514 (2)	0.3688 (3)	0.6091 (2)	0.0756 (7)
C5	0.4010 (2)	0.3252 (3)	0.5391 (2)	0.0854 (8)
C6	0.4465 (2)	0.2479 (3)	0.4801 (2)	0.0871 (8)
C7	0.5434 (2)	0.2137 (4)	0.4907 (2)	0.101 (1)
C8	0.5958 (2)	0.2572 (3)	0.5604 (1)	0.0724 (7)
C9	0.4858 (1)	0.5030 (2)	0.7832 (1)	0.0500 (5)
C10	0.4540 (1)	0.6672 (2)	0.7564 (1)	0.0473 (4)
C11	0.5197 (1)	0.7878 (2)	0.7389 (1)	0.0513 (5)
C12	0.4867 (2)	0.9402 (2)	0.7164 (1)	0.0660 (6)
C13	0.3882 (2)	0.9697 (3)	0.7078 (2)	0.0819 (8)
C14	0.3222 (2)	0.8496 (3)	0.7218 (2)	0.0893 (8)
C15	0.3551 (1)	0.7005 (2)	0.7470 (2)	0.0765 (7)
C16	0.6558 (1)	0.2977 (2)	0.9052 (1)	0.0454 (4)
C17	0.6717 (1)	0.1405 (2)	0.8792 (1)	0.0532 (5)
C18	0.6598 (1)	0.0126 (2)	0.9307 (1)	0.0624 (6)
C19	0.6333 (2)	0.0374 (3)	1.0086 (1)	0.0671 (6)
C20	0.6155 (2)	0.1941 (3)	1.0325 (1)	0.0805 (8)
C21	0.6256 (2)	0.3255 (3)	0.9815 (1)	0.0675 (6)
C22	0.6252 (2)	−0.1042 (4)	1.0653 (2)	0.107 (1)
H1	0.6791	0.3428	0.6924	0.057*
H2	0.4168	0.4239	0.6513	0.090*
H3	0.3311	0.3502	0.5320	0.101*
H4	0.4102	0.2171	0.4304	0.103*
H5	0.5767	0.1569	0.4484	0.120*
H6	0.6657	0.2316	0.5667	0.087*
H7	0.5900	0.7650	0.7425	0.062*
H8	0.5336	1.0270	0.7068	0.079*
H9	0.3648	1.0777	0.6913	0.098*
H10	0.2519	0.8704	0.7138	0.107*
H11	0.3076	0.6158	0.7587	0.092*
H12	0.6912	0.1206	0.8245	0.064*
H13	0.6704	−0.0983	0.9119	0.075*
H14	0.5951	0.2135	1.0871	0.097*
H15	0.6115	0.4359	0.9994	0.082*
H16	0.5598	−0.1466	1.0611	0.129*
H17	0.6401	−0.0684	1.1193	0.129*
H18	0.6705	−0.1874	1.0516	0.129*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0419 (3)	0.0405 (3)	0.0605 (3)	−0.0029 (2)	−0.0048 (2)	−0.0008 (2)
O1	0.0531 (8)	0.077 (1)	0.137 (2)	−0.0007 (7)	0.0250 (9)	0.048 (1)
O2	0.0365 (6)	0.0791 (9)	0.0739 (9)	−0.0048 (6)	−0.0024 (6)	0.0101 (7)
O3	0.080 (1)	0.0389 (7)	0.083 (1)	−0.0023 (6)	−0.0143 (8)	−0.0095 (7)
C1	0.0367 (8)	0.0359 (8)	0.062 (1)	−0.0006 (6)	−0.0018 (7)	0.0057 (7)
C2	0.0421 (8)	0.0407 (8)	0.060 (1)	0.0017 (7)	−0.0037 (7)	0.0058 (8)
C3	0.053 (1)	0.0391 (8)	0.062 (1)	−0.0017 (7)	−0.0098 (8)	0.0083 (8)
C4	0.059 (1)	0.074 (1)	0.091 (2)	0.014 (1)	−0.021 (1)	−0.017 (1)
C5	0.069 (1)	0.083 (2)	0.100 (2)	0.004 (1)	−0.034 (1)	−0.001 (1)
C6	0.093 (2)	0.094 (2)	0.071 (2)	−0.016 (1)	−0.028 (1)	0.004 (1)
C7	0.105 (2)	0.135 (2)	0.061 (1)	−0.005 (2)	−0.005 (1)	−0.018 (2)
C8	0.067 (1)	0.089 (2)	0.061 (1)	−0.002 (1)	−0.000 (1)	−0.004 (1)
C9	0.0385 (8)	0.0449 (9)	0.067 (1)	−0.0043 (7)	0.0040 (8)	0.0065 (8)
C10	0.0374 (8)	0.0420 (8)	0.063 (1)	0.0006 (7)	0.0067 (7)	−0.0038 (8)
C11	0.0415 (9)	0.0454 (9)	0.067 (1)	−0.0027 (7)	0.0028 (8)	0.0046 (8)
C12	0.060 (1)	0.046 (1)	0.092 (2)	−0.0044 (8)	0.002 (1)	0.009 (1)
C13	0.068 (1)	0.048 (1)	0.129 (2)	0.014 (1)	−0.001 (1)	0.005 (1)
C14	0.048 (1)	0.057 (1)	0.163 (3)	0.014 (1)	0.003 (1)	−0.002 (1)
C15	0.0398 (9)	0.048 (1)	0.142 (2)	0.0001 (8)	0.012 (1)	−0.001 (1)
C16	0.0418 (8)	0.0425 (8)	0.0517 (9)	0.0035 (7)	−0.0002 (7)	−0.0034 (7)
C17	0.060 (1)	0.0442 (9)	0.055 (1)	0.0059 (8)	0.0021 (8)	−0.0056 (8)
C18	0.065 (1)	0.0443 (9)	0.077 (1)	0.0034 (9)	−0.006 (1)	0.0020 (9)
C19	0.062 (1)	0.067 (1)	0.072 (1)	−0.002 (1)	−0.001 (1)	0.018 (1)
C20	0.099 (2)	0.088 (2)	0.056 (1)	0.006 (1)	0.019 (1)	0.004 (1)
C21	0.084 (1)	0.057 (1)	0.063 (1)	0.010 (1)	0.013 (1)	−0.009 (1)
C22	0.107 (2)	0.104 (2)	0.109 (2)	−0.013 (2)	−0.007 (2)	0.054 (2)

Geometric parameters (Å, º)

S1—O2	1.431 (1)	C17—C18	1.375 (3)
S1—O3	1.435 (1)	C18—C19	1.383 (3)
S1—C1	1.770 (2)	C19—C20	1.377 (3)
S1—C16	1.758 (2)	C19—C22	1.511 (4)
O1—C9	1.201 (3)	C20—C21	1.389 (3)
C1—C2	1.332 (3)	C2—H1	0.9800
C1—C9	1.510 (2)	C4—H2	0.9800
C2—C3	1.467 (2)	C5—H3	0.9800
C3—C4	1.389 (3)	C6—H4	0.9800
C3—C8	1.374 (3)	C7—H5	0.9800
C4—C5	1.375 (4)	C8—H6	0.9800
C5—C6	1.352 (4)	C11—H7	0.9800
C6—C7	1.359 (4)	C12—H8	0.9800
C7—C8	1.383 (4)	C13—H9	0.9800
C9—C10	1.483 (2)	C14—H10	0.9800
C10—C11	1.381 (2)	C15—H11	0.9800
C10—C15	1.383 (3)	C17—H12	0.9800
C11—C12	1.380 (3)	C18—H13	0.9800
C12—C13	1.371 (3)	C20—H14	0.9800
C13—C14	1.368 (3)	C21—H15	0.9800
C14—C15	1.367 (3)	C22—H16	0.9600
C16—C17	1.386 (2)	C22—H17	0.9600
C16—C21	1.379 (3)	C22—H18	0.9600
O3—S1—O2	118.45 (9)	C22—C19—C20	121.5 (2)
C1—S1—O2	107.87 (8)	C1—C2—H1	114.7830
C16—S1—O2	108.34 (8)	H1—C2—C3	114.7090
C1—S1—O3	107.31 (8)	C3—C4—H2	119.5638
C16—S1—O3	108.57 (9)	C3—C8—H6	119.7561
S1—C1—C2	118.0 (1)	H2—C4—C5	119.5273
S1—C1—C9	114.3 (1)	C4—C5—H3	119.5360
C16—S1—C1	105.58 (8)	H3—C5—C6	119.5859
S1—C16—C17	119.3 (1)	C5—C6—H4	120.4741
S1—C16—C21	120.4 (1)	C6—C7—H5	119.4192
O1—C9—C1	119.6 (2)	H4—C6—C7	120.4840
O1—C9—C10	122.0 (2)	C7—C8—H6	119.7643
C9—C1—C2	127.6 (2)	H5—C7—C8	119.4226
C1—C2—C3	130.5 (2)	C10—C11—H7	119.8600
C1—C9—C10	118.4 (2)	C10—C15—H11	119.4179
C2—C3—C4	125.0 (2)	H7—C11—C12	119.8188
C2—C3—C8	117.4 (2)	C11—C12—H8	120.0883
C8—C3—C4	117.5 (2)	H8—C12—C13	120.1358
C3—C4—C5	120.9 (2)	C12—C13—H9	119.7136
C3—C8—C7	120.5 (2)	C13—C14—H10	120.2164
C4—C5—C6	120.9 (2)	H9—C13—C14	119.7399
C5—C6—C7	119.0 (3)	C14—C15—H11	119.3338
C6—C7—C8	121.2 (3)	H10—C14—C15	120.2811
C9—C10—C11	122.4 (1)	C16—C17—H12	120.1804
C9—C10—C15	119.1 (2)	C16—C21—H15	120.6509
C15—C10—C11	118.5 (2)	H12—C17—C18	120.1588
C10—C11—C12	120.3 (2)	C17—C18—H13	119.2909
C10—C15—C14	121.2 (2)	H13—C18—C19	119.3733
C11—C12—C13	119.8 (2)	C19—C20—H14	119.0922
C12—C13—C14	120.5 (2)	C19—C22—H16	109.4586
C13—C14—C15	119.5 (2)	C19—C22—H17	109.4853
C21—C16—C17	120.2 (2)	C19—C22—H18	109.4293
C16—C17—C18	119.7 (2)	C20—C21—H15	120.5637
C16—C21—C20	118.8 (2)	H14—C20—C21	119.0561
C17—C18—C19	121.3 (2)	H17—C22—H16	109.4959
C18—C19—C20	118.1 (2)	H18—C22—H16	109.4737
C18—C19—C22	120.5 (2)	H18—C22—H17	109.4844
C19—C20—C21	121.9 (2)
O2—S1—C1—C2	17.5 (2)	C4—C5—C6—C7	−0.2 (4)
O2—S1—C1—C9	−166.9 (1)	C5—C6—C7—C8	−0.3 (5)
O3—S1—C1—C2	146.2 (1)	C6—C7—C8—C3	0.1 (4)
O3—S1—C1—C9	−38.2 (2)	O1—C9—C10—C11	157.3 (2)
C16—S1—C1—C2	−98.1 (2)	O1—C9—C10—C15	−24.2 (4)
C16—S1—C1—C9	77.5 (1)	C1—C9—C10—C11	−23.3 (3)
O2—S1—C16—C17	−47.7 (2)	C1—C9—C10—C15	155.3 (2)
O2—S1—C16—C21	131.2 (2)	C9—C10—C11—C12	−178.1 (2)
O3—S1—C16—C17	−177.5 (1)	C15—C10—C11—C12	3.3 (3)
O3—S1—C16—C21	1.3 (2)	C9—C10—C15—C14	−179.5 (3)
C1—S1—C16—C17	67.6 (2)	C11—C10—C15—C14	−0.9 (4)
C1—S1—C16—C21	−113.5 (2)	C10—C11—C12—C13	−3.1 (4)
S1—C1—C2—C3	176.5 (2)	C11—C12—C13—C14	0.5 (5)
C9—C1—C2—C3	1.6 (3)	C12—C13—C14—C15	1.9 (5)
S1—C1—C9—O1	−80.2 (2)	C13—C14—C15—C10	−1.7 (5)
S1—C1—C9—C10	100.4 (2)	S1—C16—C17—C18	177.0 (2)
C2—C1—C9—O1	94.9 (3)	C21—C16—C17—C18	−1.8 (3)
C2—C1—C9—C10	−84.5 (3)	S1—C16—C21—C20	−176.3 (2)
C1—C2—C3—C4	−0.5 (4)	C17—C16—C21—C20	2.6 (4)
C1—C2—C3—C8	−177.7 (2)	C16—C17—C18—C19	−0.7 (4)
C2—C3—C4—C5	−178.4 (2)	C17—C18—C19—C20	2.3 (4)
C8—C3—C4—C5	−1.2 (4)	C17—C18—C19—C22	−177.1 (3)
C2—C3—C8—C7	178.1 (3)	C18—C19—C20—C21	−1.5 (4)
C4—C3—C8—C7	0.7 (4)	C22—C19—C20—C21	177.9 (3)
C3—C4—C5—C6	1.0 (5)	C19—C20—C21—C16	−0.9 (4)