(E)-1,2-Diphenyl­vinyl p-toluene­sulfonate

Cui, D.; Meng, Q.; Zhang, C.; Gu, J.

doi:10.1107/S160053680802607X

organic compounds

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ISSN: 2056-9890

Volume 64| Part 9| September 2008| Page o1787

doi:10.1107/S160053680802607X

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(E)-1,2-Diphenylvinyl p-toluenesulfonate

Dongmei Cui,^a ^* Qian Meng,^a Chen Zhang ^b and Jianming Gu ^b

^aZhejiang University of Technology, College of Pharmaceutical Science, Hangzhou 310014, People's Republic of China, and ^bZhejiang University, Hangzhou 310058, People's Republic of China
^*Correspondence e-mail: cuidongmei@zjut.edu.cn

(Received 8 May 2008; accepted 13 August 2008; online 20 August 2008)

The title compound, C₂₁H₁₈O₃S, is the E isomer, the ester oxy link being trans to one of the phenyl groups. The planes of the phenyl substituents at the vinyl C atoms form a dihedral angle of 66.32 (7)° with each other. The vinyl group shows noticeable non-planarity, the C(Ph)—C=C—C(Ph) torsion angle being 8.4 (3)°.

Related literature

For related literature, see: Ishikawa et al. (2001 ); Peterson & Indelicato (1968 ); Yoshihiro & Atsushi (1993 ); Larson (1970 ).

Experimental

Crystal data

C₂₁H₁₈O₃S
M_r = 350.43
Monoclinic, P 2₁ /c
a = 19.8000 (7) Å
b = 5.8289 (2) Å
c = 15.5228 (7) Å
β = 97.2226 (12)°
V = 1777.31 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 296 (1) K
0.50 × 0.50 × 0.20 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.879, T_max = 0.961
16497 measured reflections
4064 independent reflections
2454 reflections with I > 2σ(I)
R_int = 0.037

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.115
S = 1.01
4064 reflections
245 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.37 e Å⁻³

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 (Betteridge et al., 2003); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: CrystalStructure.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680802607X/ya2077sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680802607X/ya2077Isup2.hkl

checkCIF report

Comment top

The enol sulfonates have been extensively studied as substrates in solvolytic displacement reactions (Peterson & Indelicato, 1968) and as starting materials or intermediates in the synthesis of various medicines and agrichemicals (Yoshihiro & Atsushi, 1993). They also play important role in the synthesis of cephalosporin derivates (Ishikawa et al., 2001). As a part of our studies of enol sulfonates, we synthesized the title compound and determined its crystal structure.

The title compound is shown to be an E-isomer with the ester O1 oxygen in trans-position to the phenyl carbon atom C3. The C1=C2 double bond environment is notceably non-planar with the torsion angle C3—C2—C1—C9 being equal to 8.4 (3)°. The planes of Ph-groups C3—C8 and C9—C14 form dihedral angle of 66.32 (7)° with each other, whereas the C9—C14 plane is approximately parallel to the benzene plane C15—C20 of p-toluenesulfonic group; corresponding dihedral angle is equal to 10.5 (2)°.

Related literature top

For related literature, see: Ishikawa et al. (2001); Peterson & Indelicato (1968); Yoshihiro & Atsushi (1993); Larson (1970).

Experimental top

1,2-Diphenylethanone (0.84 mg, 4.3 mmol) in 2 ml of THF was slowly added to 5.00 mmol of freshly prepared lithium diisopropylamide at 195 K and stirred for 1 h. The resulting pale yellow solution was transferred to a solution of 3.0 g (9.2 mmol) of toluenesulfonic anhydride in 20 ml of THF at 273 K via a double-tip needle. This mixture was warmed to room temperature over a 3 h period and then poured into 200 ml of cold saturated NaHCO₃. Extraction into ether (250 ml) was followed by washing with brine (250 ml) and water (250 ml) and drying (MgSO₄). Evaporation of the solvent left a yellow-brown oil (0.94 g, 80% yield). Recrystallization from 20% ether/pentane gave colourless crystals.

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); 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 (Rigaku/MSC, 2004).

Figures top

Fig. 1. Molecular structure of the title compound, showing 30% probability displacement ellipsoids and atom numbering scheme.

(E)-1,2-Diphenylvinyl p-toluenesulfonate top

Crystal data top

C₂₁H₁₈O₃S	F(000) = 736.00
M_r = 350.43	D_x = 1.310 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71075 Å
Hall symbol: -P 2ybc	Cell parameters from 11320 reflections
a = 19.8000 (7) Å	θ = 3.1–27.4°
b = 5.8289 (2) Å	µ = 0.20 mm⁻¹
c = 15.5228 (7) Å	T = 296 K
β = 97.2226 (12)°	Plate, colourless
V = 1777.31 (12) Å³	0.50 × 0.50 × 0.20 mm
Z = 4

Data collection top

Rigaku R-AXIS RAPID diffractometer	2454 reflections with I > 2σ(I)
Detector resolution: 10.00 pixels mm^-1	R_int = 0.037
ω scans	θ_max = 27.5°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −25→25
T_min = 0.879, T_max = 0.961	k = −6→7
16497 measured reflections	l = −20→20
4064 independent reflections

Refinement top

Refinement on F²	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.035	w = 1/[0.0007F_o² + σ(F_o²)]/(4F_o²)
wR(F²) = 0.115	(Δ/σ)_max < 0.001
S = 1.01	Δρ_max = 0.32 e Å⁻³
4064 reflections	Δρ_min = −0.37 e Å⁻³
245 parameters	Extinction correction: Larson (1970)
0 restraints	Extinction coefficient: 704 (41)

Crystal data top

C₂₁H₁₈O₃S	V = 1777.31 (12) Å³
M_r = 350.43	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 19.8000 (7) Å	µ = 0.20 mm⁻¹
b = 5.8289 (2) Å	T = 296 K
c = 15.5228 (7) Å	0.50 × 0.50 × 0.20 mm
β = 97.2226 (12)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	4064 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	2454 reflections with I > 2σ(I)
T_min = 0.879, T_max = 0.961	R_int = 0.037
16497 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.115	H-atom parameters constrained
S = 1.01	Δρ_max = 0.32 e Å⁻³
4064 reflections	Δρ_min = −0.37 e Å⁻³
245 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.18392 (2)	0.36995 (9)	0.40582 (3)	0.04917 (14)
O1	0.24688 (6)	0.5425 (2)	0.41891 (8)	0.0490 (3)
O2	0.20815 (6)	0.1464 (2)	0.39044 (10)	0.0626 (4)
O3	0.14984 (6)	0.4139 (2)	0.47932 (9)	0.0692 (4)
C1	0.30475 (8)	0.5083 (2)	0.37345 (12)	0.0423 (4)
C2	0.36167 (9)	0.4467 (3)	0.42212 (12)	0.0504 (5)
C3	0.43026 (8)	0.4338 (3)	0.39505 (12)	0.0457 (5)
C4	0.47282 (10)	0.2516 (3)	0.42163 (13)	0.0588 (6)
C5	0.53825 (10)	0.2424 (3)	0.40017 (14)	0.0636 (6)
C6	0.56265 (9)	0.4158 (3)	0.35334 (13)	0.0564 (6)
C7	0.52180 (9)	0.5978 (3)	0.32689 (13)	0.0564 (6)
C8	0.45589 (9)	0.6074 (3)	0.34753 (12)	0.0528 (5)
C9	0.29281 (8)	0.5511 (2)	0.27937 (12)	0.0399 (4)
C10	0.31048 (9)	0.3861 (3)	0.22233 (12)	0.0463 (5)
C11	0.29633 (10)	0.4197 (3)	0.13398 (12)	0.0563 (6)
C12	0.26427 (10)	0.6160 (3)	0.10150 (12)	0.0570 (6)
C13	0.24713 (9)	0.7817 (3)	0.15732 (13)	0.0554 (6)
C14	0.26083 (8)	0.7515 (3)	0.24614 (12)	0.0469 (5)
C15	0.13442 (8)	0.4713 (3)	0.31215 (12)	0.0437 (5)
C16	0.13277 (9)	0.3540 (3)	0.23505 (12)	0.0490 (5)
C17	0.09787 (9)	0.4460 (3)	0.16026 (13)	0.0551 (5)
C18	0.06416 (9)	0.6543 (3)	0.16162 (13)	0.0558 (6)
C19	0.06504 (9)	0.7662 (3)	0.24064 (16)	0.0588 (6)
C20	0.09969 (9)	0.6786 (3)	0.31559 (13)	0.0538 (5)
C21	0.02903 (12)	0.7611 (4)	0.07986 (17)	0.0876 (9)
H2	0.3579	0.4074	0.4794	0.060*
H4	0.4570	0.1340	0.4543	0.071*
H5	0.5659	0.1178	0.4176	0.076*
H6	0.6070	0.4097	0.3395	0.068*
H7	0.5383	0.7155	0.2949	0.068*
H8	0.4284	0.7320	0.3293	0.063*
H10	0.3320	0.2521	0.2436	0.056*
H11	0.3086	0.3082	0.0960	0.068*
H12	0.2543	0.6363	0.0418	0.068*
H13	0.2261	0.9158	0.1353	0.066*
H14	0.2488	0.8644	0.2837	0.056*
H16	0.1550	0.2138	0.2332	0.059*
H17	0.0970	0.3668	0.1081	0.066*
H19	0.0416	0.9038	0.2429	0.071*
H20	0.1000	0.7564	0.3679	0.065*
H211	0.0549	0.7310	0.0327	0.105*
H212	0.0255	0.9238	0.0878	0.105*
H213	−0.0157	0.6967	0.0668	0.105*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0464 (2)	0.0604 (3)	0.0419 (3)	−0.0014 (2)	0.0103 (2)	0.0001 (2)
O1	0.0444 (6)	0.0644 (8)	0.0398 (7)	−0.0042 (5)	0.0116 (5)	−0.0115 (6)
O2	0.0705 (8)	0.0510 (8)	0.0651 (10)	0.0076 (6)	0.0040 (7)	0.0045 (7)
O3	0.0573 (7)	0.1060 (12)	0.0483 (9)	−0.0027 (7)	0.0228 (6)	0.0018 (8)
C1	0.0413 (8)	0.0491 (10)	0.0376 (10)	−0.0001 (7)	0.0088 (7)	−0.0053 (8)
C2	0.0480 (9)	0.0689 (12)	0.0343 (10)	−0.0031 (9)	0.0054 (8)	0.0055 (9)
C3	0.0437 (9)	0.0600 (11)	0.0325 (10)	−0.0006 (8)	0.0018 (7)	0.0033 (8)
C4	0.0571 (11)	0.0653 (13)	0.0539 (13)	0.0045 (10)	0.0070 (9)	0.0190 (10)
C5	0.0534 (11)	0.0721 (14)	0.0648 (14)	0.0137 (10)	0.0058 (10)	0.0122 (12)
C6	0.0426 (9)	0.0760 (14)	0.0501 (12)	−0.0005 (10)	0.0040 (8)	−0.0036 (11)
C7	0.0472 (9)	0.0674 (13)	0.0548 (13)	−0.0070 (9)	0.0073 (9)	0.0082 (10)
C8	0.0494 (10)	0.0567 (11)	0.0516 (12)	0.0012 (9)	0.0042 (8)	0.0091 (10)
C9	0.0379 (8)	0.0456 (9)	0.0362 (10)	−0.0007 (7)	0.0053 (7)	−0.0021 (8)
C10	0.0493 (9)	0.0477 (10)	0.0425 (11)	0.0045 (8)	0.0090 (8)	−0.0040 (9)
C11	0.0644 (11)	0.0656 (13)	0.0404 (12)	−0.0031 (10)	0.0130 (9)	−0.0133 (10)
C12	0.0605 (11)	0.0732 (14)	0.0367 (11)	−0.0102 (10)	0.0032 (9)	0.0061 (10)
C13	0.0543 (10)	0.0537 (12)	0.0568 (13)	−0.0014 (9)	0.0020 (9)	0.0139 (10)
C14	0.0489 (9)	0.0448 (10)	0.0475 (12)	−0.0012 (8)	0.0082 (8)	−0.0029 (9)
C15	0.0386 (8)	0.0485 (10)	0.0450 (11)	−0.0022 (7)	0.0093 (7)	−0.0020 (8)
C16	0.0466 (9)	0.0489 (10)	0.0516 (12)	−0.0001 (8)	0.0073 (8)	−0.0067 (9)
C17	0.0523 (10)	0.0654 (12)	0.0471 (12)	−0.0056 (10)	0.0044 (9)	−0.0079 (10)
C18	0.0415 (9)	0.0679 (13)	0.0576 (14)	−0.0036 (9)	0.0046 (9)	0.0085 (11)
C19	0.0461 (10)	0.0553 (12)	0.0763 (16)	0.0075 (9)	0.0124 (10)	0.0068 (11)
C20	0.0513 (10)	0.0544 (11)	0.0580 (13)	0.0020 (9)	0.0160 (9)	−0.0078 (10)
C21	0.0740 (14)	0.105 (2)	0.0801 (19)	0.0060 (14)	−0.0029 (13)	0.0261 (16)

Geometric parameters (Å, º) top

S1—O1	1.5946 (12)	C17—C18	1.387 (2)
S1—O2	1.4189 (14)	C18—C19	1.387 (3)
S1—O3	1.4200 (15)	C18—C21	1.503 (3)
S1—C15	1.7508 (17)	C19—C20	1.373 (2)
O1—C1	1.433 (2)	C2—H2	0.930
C1—C2	1.325 (2)	C4—H4	0.930
C1—C9	1.471 (2)	C5—H5	0.930
C2—C3	1.473 (2)	C6—H6	0.930
C3—C4	1.386 (2)	C7—H7	0.930
C3—C8	1.386 (2)	C8—H8	0.930
C4—C5	1.379 (2)	C10—H10	0.930
C5—C6	1.368 (3)	C11—H11	0.930
C6—C7	1.366 (2)	C12—H12	0.930
C7—C8	1.383 (2)	C13—H13	0.930
C9—C10	1.382 (2)	C14—H14	0.930
C9—C14	1.396 (2)	C16—H16	0.930
C10—C11	1.379 (2)	C17—H17	0.930
C11—C12	1.374 (2)	C19—H19	0.930
C12—C13	1.368 (3)	C20—H20	0.930
C13—C14	1.383 (2)	C21—H211	0.960
C15—C16	1.375 (2)	C21—H212	0.960
C15—C20	1.395 (2)	C21—H213	0.960
C16—C17	1.382 (2)

O1—S1—O2	108.97 (7)	C1—C2—H2	116.6
O1—S1—O3	103.10 (8)	C3—C2—H2	116.6
O1—S1—C15	103.89 (7)	C3—C4—H4	119.6
O2—S1—O3	120.38 (9)	C5—C4—H4	119.6
O2—S1—C15	109.63 (8)	C4—C5—H5	119.8
O3—S1—C15	109.48 (8)	C6—C5—H5	119.8
S1—O1—C1	120.67 (10)	C5—C6—H6	120.1
O1—C1—C2	115.62 (16)	C7—C6—H6	120.1
O1—C1—C9	115.25 (13)	C6—C7—H7	119.9
C2—C1—C9	129.13 (17)	C8—C7—H7	119.9
C1—C2—C3	126.85 (18)	C3—C8—H8	119.6
C2—C3—C4	120.13 (17)	C7—C8—H8	119.6
C2—C3—C8	121.81 (16)	C9—C10—H10	119.9
C4—C3—C8	117.94 (16)	C11—C10—H10	119.9
C3—C4—C5	120.82 (19)	C10—C11—H11	119.7
C4—C5—C6	120.35 (19)	C12—C11—H11	119.7
C5—C6—C7	119.88 (18)	C11—C12—H12	120.1
C6—C7—C8	120.15 (19)	C13—C12—H12	120.1
C3—C8—C7	120.86 (17)	C12—C13—H13	119.7
C1—C9—C10	119.73 (15)	C14—C13—H13	119.7
C1—C9—C14	121.18 (16)	C9—C14—H14	120.1
C10—C9—C14	119.02 (17)	C13—C14—H14	120.1
C9—C10—C11	120.18 (17)	C15—C16—H16	120.2
C10—C11—C12	120.66 (19)	C17—C16—H16	120.2
C11—C12—C13	119.71 (18)	C16—C17—H17	119.4
C12—C13—C14	120.55 (18)	C18—C17—H17	119.4
C9—C14—C13	119.88 (17)	C18—C19—H19	119.2
S1—C15—C16	120.30 (13)	C20—C19—H19	119.2
S1—C15—C20	119.19 (14)	C15—C20—H20	120.5
C16—C15—C20	120.42 (16)	C19—C20—H20	120.5
C15—C16—C17	119.51 (17)	C18—C21—H211	109.5
C16—C17—C18	121.17 (19)	C18—C21—H212	109.5
C17—C18—C19	118.19 (18)	C18—C21—H213	109.5
C17—C18—C21	121.5 (2)	H211—C21—H212	109.5
C19—C18—C21	120.32 (19)	H211—C21—H213	109.5
C18—C19—C20	121.60 (18)	H212—C21—H213	109.5
C15—C20—C19	119.09 (19)

O2—S1—O1—C1	32.69 (14)	C3—C4—C5—C6	1.1 (3)
O3—S1—O1—C1	161.67 (12)	C4—C5—C6—C7	−0.7 (3)
O1—S1—C15—C16	106.36 (15)	C5—C6—C7—C8	0.1 (2)
O1—S1—C15—C20	−70.21 (15)	C6—C7—C8—C3	−0.0 (2)
C15—S1—O1—C1	−84.11 (13)	C1—C9—C10—C11	176.68 (16)
O2—S1—C15—C16	−9.98 (17)	C1—C9—C14—C13	−176.66 (15)
O2—S1—C15—C20	173.46 (14)	C10—C9—C14—C13	0.2 (2)
O3—S1—C15—C16	−144.06 (15)	C14—C9—C10—C11	−0.3 (2)
O3—S1—C15—C20	39.38 (17)	C9—C10—C11—C12	−0.4 (2)
S1—O1—C1—C2	−110.89 (15)	C10—C11—C12—C13	1.0 (3)
S1—O1—C1—C9	70.28 (17)	C11—C12—C13—C14	−1.0 (2)
O1—C1—C2—C3	−170.22 (16)	C12—C13—C14—C9	0.4 (2)
O1—C1—C9—C10	−127.99 (16)	S1—C15—C16—C17	−174.80 (14)
O1—C1—C9—C14	48.9 (2)	S1—C15—C20—C19	175.21 (14)
C2—C1—C9—C10	53.4 (2)	C16—C15—C20—C19	−1.4 (2)
C2—C1—C9—C14	−129.8 (2)	C20—C15—C16—C17	1.7 (2)
C9—C1—C2—C3	8.4 (3)	C15—C16—C17—C18	−0.3 (2)
C1—C2—C3—C4	−138.5 (2)	C16—C17—C18—C19	−1.4 (2)
C1—C2—C3—C8	45.6 (2)	C16—C17—C18—C21	176.93 (19)
C2—C3—C4—C5	−177.00 (18)	C17—C18—C19—C20	1.8 (2)
C2—C3—C8—C7	176.40 (18)	C21—C18—C19—C20	−176.57 (19)
C4—C3—C8—C7	0.4 (2)	C18—C19—C20—C15	−0.4 (2)
C8—C3—C4—C5	−1.0 (2)

Experimental details

Crystal data
Chemical formula	C₂₁H₁₈O₃S
M_r	350.43
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	19.8000 (7), 5.8289 (2), 15.5228 (7)
β (°)	97.2226 (12)
V (Å³)	1777.31 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.50 × 0.50 × 0.20

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.879, 0.961
No. of measured, independent and observed [I > 2σ(I)] reflections	16497, 4064, 2454
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.115, 1.01
No. of reflections	4064
No. of parameters	245
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.37

Computer programs: PROCESS-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2004), SIR97 (Altomare et al., 1999), CRYSTALS (Watkin et al., 1996), ORTEP-3 for Windows (Farrugia, 1997).

Acknowledgements

This work was partially supported by the Natural Science Foundation of China (20572094, 20672099). Mr Xinju Ma of the College of Pharmaceutical Science of Zhejiang University of Technology is acknowledged for interpretation and discussion of the structural results.

References

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