(E)-1,2-Diphenyl-ethenyl methane-sulfonate.

In the title compound, C(15)H(14)O(3)S, the dihedral angle between the two benzene rings is 59.3 (8)°. The crystal structure is stabilized by weak inter-molecular C-H⋯π inter-actions between the benzene rings and the central ethyl-ene bridge, and a weak non-classical C-H⋯O hydrogen bond occurs in the structure.

Related literature

For general background to the design and synthesis of vinyl sulfonate derivatives, see: Limmert et al. (2005 ▶). For related structures, see: Cui et al. (2009 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C15H14O3S

M = 274.33

Orthorhombic,

a = 8.3789 (3) Å

b = 11.1397 (4) Å

c = 14.8365 (5) Å

V = 1384.82 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.23 mm−1

T = 296 K

0.41 × 0.39 × 0.29 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.887, T max = 0.934

13673 measured reflections

3163 independent reflections

2606 reflections with F 2 > 2.0σ(F 2)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.092

S = 1.00

3163 reflections

174 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.20 e Å−3

Absolute structure: Flack (1983 ▶), 1341 Friedel Pairs

Flack parameter: −0.03 (7)

Data collection: PROCESS-AUTO (Rigaku, 2006 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku, 2007 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: CrystalStructure (Rigaku Americas, 2007 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681001281X/bq2190sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681001281X/bq2190Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C15H14O3S	F(000) = 576.00
Mr = 274.33	Dx = 1.316 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71075 Å
Hall symbol: P 2ac 2ab	Cell parameters from 11138 reflections
a = 8.3789 (3) Å	θ = 3.0–27.4°
b = 11.1397 (4) Å	µ = 0.23 mm−1
c = 14.8365 (5) Å	T = 296 K
V = 1384.82 (8) Å3	Chunk, colorless
Z = 4	0.41 × 0.39 × 0.29 mm

Rigaku R-AXIS RAPID diffractometer	2606 reflections with F2 > 2.0σ(F2)
Detector resolution: 10.00 pixels mm-1	Rint = 0.026
ω scans	θmax = 27.4°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −10→10
Tmin = 0.887, Tmax = 0.934	k = −13→14
13673 measured reflections	l = −19→18
3163 independent reflections

Refinement on F2	(Δ/σ)max < 0.001
R[F2 > 2σ(F2)] = 0.032	Δρmax = 0.15 e Å−3
wR(F2) = 0.092	Δρmin = −0.20 e Å−3
S = 1.00	Extinction correction: SHELXL97 (Sheldrick, 2008)
3163 reflections	Extinction coefficient: 0.0173 (19)
174 parameters	Absolute structure: Flack (1983), 1341 Friedel Pairs
H-atom parameters constrained	Flack parameter: −0.03 (7)
w = 1/[σ2(Fo2) + (0.0507P)2 + 0.1656P] where P = (Fo2 + 2Fc2)/3

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).

	x	y	z	Uiso*/Ueq
S1	0.61979 (6)	0.70614 (5)	0.09128 (3)	0.05358 (15)
O1	0.47962 (16)	0.75814 (11)	0.15261 (8)	0.0510 (3)
O2	0.6188 (2)	0.78154 (19)	0.01488 (11)	0.1006 (6)
O3	0.6001 (2)	0.58046 (14)	0.08152 (12)	0.0874 (5)
C1	0.3992 (2)	0.68265 (13)	0.21579 (10)	0.0413 (3)
C2	0.4741 (2)	0.68403 (14)	0.30602 (11)	0.0426 (3)
C3	0.4984 (2)	0.57768 (18)	0.35269 (12)	0.0528 (4)
C4	0.5742 (2)	0.5788 (2)	0.43570 (13)	0.0720 (6)
C5	0.6285 (3)	0.6847 (2)	0.47133 (13)	0.0848 (7)
C6	0.6049 (3)	0.7911 (2)	0.42591 (13)	0.0842 (7)
C7	0.5272 (2)	0.7914 (2)	0.34348 (12)	0.0635 (5)
C8	0.2696 (2)	0.62793 (16)	0.18488 (12)	0.0462 (4)
C9	0.1462 (2)	0.56029 (14)	0.23397 (11)	0.0429 (3)
C10	0.0528 (2)	0.47874 (19)	0.18648 (13)	0.0553 (4)
C11	−0.0714 (2)	0.4185 (2)	0.22810 (16)	0.0649 (5)
C12	−0.1058 (2)	0.43858 (18)	0.31661 (16)	0.0612 (5)
C13	−0.0169 (2)	0.51958 (19)	0.36462 (14)	0.0608 (5)
C14	0.1080 (2)	0.57984 (17)	0.32428 (12)	0.0522 (4)
C15	0.7899 (2)	0.7341 (2)	0.15510 (18)	0.0714 (6)
H3	0.4637	0.5054	0.3282	0.063*
H4	0.5884	0.5075	0.4673	0.086*
H5	0.6815	0.6847	0.5264	0.102*
H6	0.6411	0.8628	0.4506	0.101*
H7	0.5106	0.8634	0.3132	0.076*
H8	0.2544	0.6331	0.1229	0.055*
H10	0.0741	0.4645	0.1259	0.066*
H11	−0.1320	0.3637	0.1954	0.078*
H12	−0.1891	0.3975	0.3443	0.073*
H13	−0.0409	0.5341	0.4248	0.073*
H14	0.1677	0.6343	0.3578	0.063*
H151	0.8829	0.7131	0.1208	0.086*
H152	0.7940	0.8178	0.1705	0.086*
H153	0.7865	0.6870	0.2092	0.086*

	U11	U22	U33	U12	U13	U23
S1	0.0561 (2)	0.0659 (2)	0.0387 (2)	−0.0098 (2)	0.0083 (2)	−0.0016 (2)
O1	0.0526 (7)	0.0517 (6)	0.0486 (6)	0.0011 (5)	0.0082 (5)	0.0140 (5)
O2	0.0944 (13)	0.1520 (18)	0.0553 (8)	0.0003 (14)	0.0209 (9)	0.0421 (10)
O3	0.0931 (12)	0.0749 (10)	0.0941 (11)	−0.0237 (9)	0.0330 (11)	−0.0417 (9)
C1	0.0450 (9)	0.0403 (8)	0.0387 (7)	0.0011 (7)	0.0059 (7)	0.0078 (6)
C2	0.0409 (8)	0.0484 (9)	0.0384 (7)	−0.0008 (7)	0.0074 (6)	−0.0006 (7)
C3	0.0595 (11)	0.0550 (10)	0.0437 (9)	0.0102 (9)	−0.0020 (8)	0.0018 (8)
C4	0.0755 (15)	0.0970 (17)	0.0437 (10)	0.0231 (14)	−0.0026 (9)	0.0089 (11)
C5	0.0799 (16)	0.136 (2)	0.0381 (9)	−0.0057 (19)	−0.0035 (11)	−0.0126 (13)
C6	0.1004 (19)	0.1041 (18)	0.0483 (11)	−0.0390 (17)	0.0141 (12)	−0.0247 (12)
C7	0.0851 (15)	0.0571 (10)	0.0484 (9)	−0.0150 (11)	0.0131 (10)	−0.0055 (9)
C8	0.0468 (9)	0.0533 (10)	0.0384 (8)	0.0025 (8)	−0.0015 (7)	0.0060 (7)
C9	0.0408 (9)	0.0441 (8)	0.0438 (8)	0.0030 (7)	−0.0029 (7)	0.0030 (7)
C10	0.0524 (10)	0.0632 (11)	0.0504 (9)	−0.0025 (9)	−0.0063 (9)	−0.0050 (9)
C11	0.0552 (12)	0.0616 (12)	0.0777 (14)	−0.0128 (10)	−0.0067 (10)	−0.0075 (11)
C12	0.0477 (10)	0.0565 (10)	0.0795 (13)	−0.0095 (9)	0.0092 (10)	0.0034 (10)
C13	0.0573 (12)	0.0659 (12)	0.0591 (11)	−0.0072 (10)	0.0161 (10)	−0.0025 (10)
C14	0.0493 (9)	0.0560 (10)	0.0511 (9)	−0.0091 (9)	0.0067 (9)	−0.0061 (8)
C15	0.0518 (11)	0.0768 (15)	0.0857 (16)	−0.0016 (11)	0.0009 (10)	−0.0069 (13)

S1—O1	1.5946 (13)	C11—C12	1.363 (3)
S1—O2	1.4108 (18)	C12—C13	1.370 (3)
S1—O3	1.4172 (17)	C13—C14	1.380 (2)
S1—C15	1.739 (2)	C3—H3	0.930
O1—C1	1.428 (2)	C4—H4	0.930
C1—C2	1.478 (2)	C5—H5	0.930
C1—C8	1.328 (2)	C6—H6	0.930
C2—C3	1.387 (2)	C7—H7	0.930
C2—C7	1.392 (2)	C8—H8	0.930
C3—C4	1.386 (2)	C10—H10	0.930
C4—C5	1.370 (4)	C11—H11	0.930
C5—C6	1.378 (4)	C12—H12	0.930
C6—C7	1.385 (3)	C13—H13	0.930
C8—C9	1.472 (2)	C14—H14	0.930
C9—C10	1.391 (2)	C15—H151	0.960
C9—C14	1.395 (2)	C15—H152	0.960
C10—C11	1.384 (3)	C15—H153	0.960
O1—S1—O2	103.76 (10)	C4—C3—H3	119.9
O1—S1—O3	109.35 (9)	C3—C4—H4	119.9
O1—S1—C15	103.16 (9)	C5—C4—H4	119.9
O2—S1—O3	120.36 (11)	C4—C5—H5	119.9
O2—S1—C15	109.61 (12)	C6—C5—H5	119.9
O3—S1—C15	109.16 (11)	C5—C6—H6	119.9
S1—O1—C1	120.53 (10)	C7—C6—H6	119.9
O1—C1—C2	112.84 (13)	C2—C7—H7	120.0
O1—C1—C8	115.45 (14)	C6—C7—H7	120.0
C2—C1—C8	131.66 (15)	C1—C8—H8	115.1
C1—C2—C3	120.36 (15)	C9—C8—H8	115.1
C1—C2—C7	120.41 (15)	C9—C10—H10	119.5
C3—C2—C7	119.18 (16)	C11—C10—H10	119.5
C2—C3—C4	120.20 (19)	C10—C11—H11	119.7
C3—C4—C5	120.2 (2)	C12—C11—H11	119.7
C4—C5—C6	120.3 (2)	C11—C12—H12	120.2
C5—C6—C7	120.1 (2)	C13—C12—H12	120.2
C2—C7—C6	120.0 (2)	C12—C13—H13	119.8
C1—C8—C9	129.70 (16)	C14—C13—H13	119.8
C8—C9—C10	118.61 (15)	C9—C14—H14	119.5
C8—C9—C14	123.81 (15)	C13—C14—H14	119.5
C10—C9—C14	117.37 (16)	S1—C15—H151	109.5
C9—C10—C11	120.93 (19)	S1—C15—H152	109.5
C10—C11—C12	120.6 (2)	S1—C15—H153	109.5
C11—C12—C13	119.6 (2)	H151—C15—H152	109.5
C12—C13—C14	120.5 (2)	H151—C15—H153	109.5
C9—C14—C13	120.97 (18)	H152—C15—H153	109.5
C2—C3—H3	119.9
O2—S1—O1—C1	154.37 (13)	C2—C3—C4—C5	−1.3 (3)
O3—S1—O1—C1	24.77 (15)	C3—C4—C5—C6	1.5 (3)
C15—S1—O1—C1	−91.29 (14)	C4—C5—C6—C7	−0.6 (4)
S1—O1—C1—C2	90.79 (14)	C5—C6—C7—C2	−0.5 (3)
S1—O1—C1—C8	−91.52 (17)	C1—C8—C9—C10	−158.77 (19)
O1—C1—C2—C3	−135.28 (16)	C1—C8—C9—C14	26.6 (2)
O1—C1—C2—C7	41.9 (2)	C8—C9—C10—C11	−175.86 (18)
O1—C1—C8—C9	−169.44 (16)	C8—C9—C14—C13	175.14 (18)
C2—C1—C8—C9	7.7 (3)	C10—C9—C14—C13	0.5 (2)
C8—C1—C2—C3	47.5 (2)	C14—C9—C10—C11	−0.9 (2)
C8—C1—C2—C7	−135.3 (2)	C9—C10—C11—C12	0.6 (3)
C1—C2—C3—C4	177.46 (18)	C10—C11—C12—C13	0.3 (3)
C1—C2—C7—C6	−176.5 (2)	C11—C12—C13—C14	−0.7 (3)
C3—C2—C7—C6	0.7 (3)	C12—C13—C14—C9	0.3 (3)
C7—C2—C3—C4	0.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O2i	0.93	2.53	3.376 (2)	152
C15—H152···Cg1ii	0.96	2.68	3.514 (1)	145

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯O2i	0.93	2.53	3.376 (2)	152
C15—H152⋯Cg1ii	0.96	2.68	3.514 (1)	145

Symmetry codes: (i) ; (ii) . Cg1 is the centroid of the C9–C14 ring.