(R)-1-Iodo-1-phenyl-2-(p-tolyl­sulfonyl)­ethene

The title compound, C₁₅H₁₃IO₂S, displays an anti conform­ation with respect to the olefinic bond. Molecules are linked by weak C—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.028
• wR factor = 0.076
• Data-to-parameter ratio = 16.1

checkCIF/PLATON results

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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.

(I)

Crystal data

C15H13IO2S	F(000) = 752.00
Mr = 384.23	Dx = 1.714 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: -P 2yn	Cell parameters from 10732 reflections
a = 8.0171 (3) Å	θ = 2.1–27.4°
b = 12.3697 (4) Å	µ = 2.29 mm^−1
c = 15.0866 (5) Å	T = 296 K
β = 95.685 (1)°	Chunk, yellow
V = 1488.77 (9) Å^3	0.40 × 0.40 × 0.25 mm
Z = 4

Data collection

Rigaku R-AXIS RAPID diffractometer	2771 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 = −10→10
Tmin = 0.414, Tmax = 0.565	k = −16→16
14526 measured reflections	l = −19→19
3396 independent reflections

Refinement

Refinement on F^2	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.028	w = 1/[0.0009Fo^2 + σ(Fo^2)]/(4Fo^2)
wR(F^2) = 0.076	(Δ/σ)max < 0.001
S = 1.03	Δρmax = 0.35 e Å^−3
2771 reflections	Δρmin = −0.78 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
I(1)	−0.14477 (2)	0.39239 (1)	0.26222 (1)	0.05997 (7)
S(1)	0.28753 (9)	0.13942 (7)	0.25764 (4)	0.0574 (2)
O(1)	0.4475 (3)	0.1884 (2)	0.2828 (2)	0.0796 (7)
O(2)	0.2596 (3)	0.0848 (2)	0.1738 (1)	0.0851 (8)
C(1)	0.1397 (3)	0.2439 (2)	0.2671 (2)	0.0515 (7)
C(2)	−0.0050 (3)	0.2602 (2)	0.2192 (1)	0.0444 (6)
C(3)	−0.0844 (3)	0.2026 (2)	0.1401 (2)	0.0448 (6)
C(4)	−0.0024 (4)	0.1924 (2)	0.0635 (2)	0.0569 (7)
C(5)	−0.0796 (5)	0.1383 (3)	−0.0096 (2)	0.0706 (9)
C(6)	−0.2369 (5)	0.0941 (2)	−0.0070 (3)	0.076 (1)
C(7)	−0.3194 (5)	0.1061 (2)	0.0682 (3)	0.072 (1)
C(8)	−0.2457 (4)	0.1603 (2)	0.1414 (2)	0.0575 (8)
C(9)	0.2420 (3)	0.0491 (2)	0.3423 (1)	0.0475 (6)
C(10)	0.1382 (4)	−0.0387 (3)	0.3235 (2)	0.0623 (8)
C(11)	0.1038 (4)	−0.1074 (2)	0.3914 (3)	0.073 (1)
C(12)	0.1717 (4)	−0.0892 (3)	0.4781 (2)	0.0653 (9)
C(13)	0.2733 (4)	−0.0017 (3)	0.4953 (2)	0.0683 (9)
C(14)	0.3109 (4)	0.0687 (3)	0.4283 (2)	0.0598 (8)
C(15)	0.1370 (6)	−0.1656 (3)	0.5522 (3)	0.099 (1)
H(1)	0.1683	0.2970	0.3144	0.062*
H(4)	0.1098	0.2235	0.0625	0.069*
H(5)	−0.0226	0.1316	−0.0638	0.084*
H(6)	−0.2897	0.0537	−0.0581	0.089*
H(7)	−0.4321	0.0760	0.0700	0.085*
H(8)	−0.3044	0.1697	0.1949	0.069*
H(10)	0.0900	−0.0510	0.2621	0.074*
H(11)	0.0304	−0.1699	0.3780	0.088*
H(13)	0.3201	0.0127	0.5566	0.082*
H(14)	0.3848	0.1311	0.4410	0.071*
H(151)	0.0364	−0.1415	0.5785	0.122*
H(152)	0.2325	−0.1664	0.5980	0.122*
H(153)	0.1187	−0.2385	0.5278	0.122*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I(1)	0.0611 (1)	0.0512 (1)	0.0671 (1)	0.01235 (7)	0.00381 (9)	−0.00691 (7)
S(1)	0.0481 (4)	0.0764 (5)	0.0489 (3)	0.0178 (3)	0.0102 (3)	0.0029 (3)
O(1)	0.044 (1)	0.105 (2)	0.092 (2)	0.005 (1)	0.018 (1)	0.026 (1)
O(2)	0.103 (2)	0.107 (2)	0.045 (1)	0.053 (1)	0.010 (1)	−0.006 (1)
C(1)	0.048 (1)	0.059 (1)	0.047 (1)	0.006 (1)	0.006 (1)	−0.004 (1)
C(2)	0.045 (1)	0.043 (1)	0.046 (1)	0.0030 (9)	0.009 (1)	0.0033 (9)
C(3)	0.047 (1)	0.041 (1)	0.046 (1)	0.0019 (9)	0.004 (1)	0.0049 (9)
C(4)	0.058 (2)	0.066 (2)	0.047 (1)	0.005 (1)	0.007 (1)	0.004 (1)
C(5)	0.094 (2)	0.071 (2)	0.046 (1)	0.019 (2)	0.003 (1)	−0.003 (1)
C(6)	0.098 (3)	0.052 (2)	0.072 (2)	0.000 (2)	−0.023 (2)	−0.006 (1)
C(7)	0.073 (2)	0.057 (2)	0.084 (2)	−0.017 (1)	−0.010 (2)	0.003 (1)
C(8)	0.055 (1)	0.053 (2)	0.064 (2)	−0.007 (1)	0.005 (1)	0.004 (1)
C(9)	0.040 (1)	0.058 (1)	0.045 (1)	0.008 (1)	0.0041 (9)	−0.006 (1)
C(10)	0.057 (2)	0.065 (2)	0.063 (2)	0.000 (1)	−0.002 (1)	−0.016 (1)
C(11)	0.059 (2)	0.059 (2)	0.101 (3)	−0.005 (1)	0.013 (2)	−0.009 (2)
C(12)	0.060 (2)	0.062 (2)	0.077 (2)	0.015 (1)	0.025 (2)	0.008 (1)
C(13)	0.071 (2)	0.083 (2)	0.050 (1)	0.004 (2)	0.003 (1)	−0.002 (1)
C(14)	0.062 (2)	0.065 (2)	0.051 (1)	−0.006 (1)	−0.004 (1)	−0.005 (1)
C(15)	0.096 (3)	0.095 (3)	0.114 (3)	0.021 (2)	0.050 (3)	0.035 (2)

Geometric parameters (Å, º)

I(1)—C(2)	2.120 (2)	C(12)—C(13)	1.364 (5)
S(1)—O(1)	1.435 (2)	C(12)—C(15)	1.511 (6)
S(1)—O(2)	1.432 (2)	C(13)—C(14)	1.388 (4)
S(1)—C(1)	1.768 (3)	C(1)—H(1)	0.9800
S(1)—C(9)	1.762 (3)	C(4)—H(4)	0.9800
C(1)—C(2)	1.320 (3)	C(5)—H(5)	0.9800
C(2)—C(3)	1.478 (3)	C(6)—H(6)	0.9800
C(3)—C(4)	1.390 (4)	C(7)—H(7)	0.9800
C(3)—C(8)	1.397 (4)	C(8)—H(8)	0.9800
C(4)—C(5)	1.383 (4)	C(10)—H(10)	0.9800
C(5)—C(6)	1.378 (6)	C(11)—H(11)	0.9800
C(6)—C(7)	1.377 (6)	C(13)—H(13)	0.9800
C(7)—C(8)	1.374 (4)	C(14)—H(14)	0.9800
C(9)—C(10)	1.381 (4)	C(15)—H(151)	0.9800
C(9)—C(14)	1.381 (3)	C(15)—H(152)	0.9800
C(10)—C(11)	1.380 (5)	C(15)—H(153)	0.9800
C(11)—C(12)	1.384 (5)
I1—C2—C1	114.4 (2)	C(15)—C(12)—C(13)	120.4 (3)
I1—C2—C3	114.8 (2)	S(1)—C(1)—H(1)	115.9832
C1—S1—O1	105.0 (1)	H(1)—C(1)—C(2)	115.1622
O(2)—S(1)—O(1)	119.4 (2)	C(3)—C(4)—H(4)	119.1637
C(9)—S(1)—O(1)	108.6 (1)	C(3)—C(8)—H(8)	119.1580
C1—S1—O2	111.6 (1)	H(4)—C(4)—C(5)	121.1359
C9—S1—O2	108.4 (1)	C(4)—C(5)—H(5)	119.8591
S1—C1—C2	128.9 (2)	H(5)—C(5)—C(6)	119.6075
C9—S1—C1	102.5 (1)	C(5)—C(6)—H(6)	120.3577
S(1)—C(9)—C(10)	120.9 (2)	C(6)—C(7)—H(7)	120.0192
S(1)—C(9)—C(14)	118.5 (2)	H(6)—C(6)—C(7)	119.9138
C1—C2—C3	130.8 (2)	C(7)—C(8)—H(8)	121.0987
C(2)—C(3)—C(8)	119.6 (2)	H(7)—C(7)—C(8)	119.2065
C(2)—C(3)—C(4)	120.9 (2)	C(9)—C(10)—H(10)	119.2968
C(8)—C(3)—C(4)	119.5 (2)	C(9)—C(14)—H(14)	119.9123
C(3)—C(4)—C(5)	119.7 (3)	H(10)—C(10)—C(11)	121.1974
C(3)—C(8)—C(7)	119.7 (3)	C(10)—C(11)—H(11)	119.4872
C(4)—C(5)—C(6)	120.5 (3)	H(11)—C(11)—C(12)	119.7022
C(5)—C(6)—C(7)	119.7 (3)	C(12)—C(13)—H(13)	119.2864
C(6)—C(7)—C(8)	120.8 (3)	C(12)—C(15)—H(151)	109.2255
C(14)—C(9)—C(10)	120.5 (3)	C(12)—C(15)—H(152)	109.9112
C(9)—C(10)—C(11)	119.5 (3)	C(12)—C(15)—H(153)	109.2739
C(9)—C(14)—C(13)	118.5 (3)	C(13)—C(14)—H(14)	121.5437
C(10)—C(11)—C(12)	120.8 (3)	H(13)—C(13)—C(14)	118.8387
C(11)—C(12)—C(13)	118.7 (3)	H(152)—C(15)—H(151)	109.4673
C(11)—C(12)—C(15)	120.8 (3)	H(153)—C(15)—H(151)	109.4735
C(12)—C(13)—C(14)	121.9 (3)	H(153)—C(15)—H(152)	109.4749

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O2^i	0.98	2.48	3.342 (4)	148
C8—H8···O1^ii	0.98	2.51	3.429 (4)	156

Symmetry codes: (i) −x, −y, −z; (ii) x−1, y, z.