Literature DB >> 21201767

(E)-1,2-Diphenyl-vinyl p-toluene-sulfonate.

Dongmei Cui, Qian Meng, Chen Zhang, Jianming Gu.

Abstract

The title compound, C(21)H(18)O(3)S, 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)°.

Entities: CellLine Chemical Disease Gene

Year: 2008 PMID： 21201767 PMCID： PMC2960522 DOI： 10.1107/S160053680802607X

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

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

Experimental

Crystal data

C21H18O3S M = 350.43 Monoclinic, 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[F 2 > 2σ(F 2)] = 0.035 wR(F 2) = 0.115 S = 1.01 4064 reflections 245 parameters H-atom parameters constrained Δρmax = 0.32 e Å−3 Δρmin = −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. Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680802607X/ya2077sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S160053680802607X/ya2077Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

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

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 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)

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).

	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*

	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)

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)

1 in total

1. Studies on anti-MRSA parenteral cephalosporins. III. Synthesis and antibacterial activity of 7beta-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2(Z)-alkoxyiminoacetamido-3.

Authors: T Ishikawa; K Kamiyama; Y Nakayama; Y Iizawa; K Okonogi; A Miyake
Journal: J Antibiot (Tokyo) Date: 2001-03 Impact factor: 2.649

1 in total