(Z)-1-Methoxy-1-phenyl-2-(4-toluene­sulfonyl)­ethene

In the title compound, C₁₆H₁₆O₃S, the methoxy group and sulfonyl moiety are cis with respect to the olefinic bond. The two benzene rings, located trans with respect to the olefin bond, are almost perpendicular to each other, forming a dihedral angle of 75.81 (11)°.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.047
• wR factor = 0.143
• Data-to-parameter ratio = 9.2

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT031_ALERT_4_B Refined Extinction Parameter within Range ......       2.30 Sigma

Alert level C
REFNR01_ALERT_3_C  Ratio of reflections to parameters is < 10 for a
            centrosymmetric structure
            sine(theta)/lambda                0.6486
            Proportion of unique data used    0.5408
            Ratio reflections to parameters   9.1667
PLAT088_ALERT_3_C Poor Data / Parameter Ratio ....................       9.17
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   3 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
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   1 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; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); 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 and Rigaku, 2004).

(I)

Crystal data

C16H16O3S	F(000) = 1216.00
Mr = 288.36	Dx = 1.296 Mg m^−3
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: -P 2n 2ab	Cell parameters from 29982 reflections
a = 29.7459 (6) Å	θ = 1.4–27.4°
b = 11.2443 (2) Å	µ = 0.22 mm^−1
c = 8.8337 (2) Å	T = 293 K
V = 2954.6 (1) Å^3	Chunk, colorless
Z = 8	0.51 × 0.40 × 0.31 mm

Data collection

Rigaku R-AXIS RAPID diffractometer	1815 reflections with F^2 > 2σ(F^2)
Detector resolution: 10.00 pixels mm^-1	Rint = 0.040
ω scans	θmax = 27.5°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −38→38
Tmin = 0.821, Tmax = 0.933	k = −14→14
21953 measured reflections	l = −8→11
3356 independent reflections

Refinement

Refinement on F^2	w = 1/[0.0035Fo^2 + σ(Fo^2)]/(4Fo^2)
R[F^2 > 2σ(F^2)] = 0.047	(Δ/σ)max < 0.001
wR(F^2) = 0.143	Δρmax = 0.24 e Å^−3
S = 1.00	Δρmin = −0.21 e Å^−3
1815 reflections	Extinction correction: Larson (1970)
198 parameters	Extinction coefficient: 131 (57)
H-atom parameters constrained

Special details

Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY

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
S1	0.39069 (2)	0.24234 (7)	0.45052 (9)	0.0594 (3)
O1	0.40544 (8)	0.1340 (2)	0.3811 (3)	0.0794 (8)
O2	0.39893 (7)	0.3527 (2)	0.3737 (3)	0.0792 (8)
O3	0.33406 (6)	0.0589 (2)	0.6033 (2)	0.0645 (7)
C1	0.3325 (1)	0.2360 (3)	0.4726 (3)	0.0574 (9)
C2	0.31018 (9)	0.1433 (2)	0.5283 (3)	0.0502 (8)
C3	0.26084 (9)	0.1311 (2)	0.5248 (3)	0.0481 (8)
C4	0.2361 (1)	0.1805 (3)	0.4067 (3)	0.0555 (8)
C5	0.1898 (1)	0.1738 (3)	0.4059 (4)	0.0660 (9)
C6	0.1677 (1)	0.1171 (3)	0.5231 (4)	0.0680 (8)
C7	0.1915 (1)	0.0681 (3)	0.6392 (4)	0.0660 (8)
C8	0.2377 (1)	0.0741 (3)	0.6400 (3)	0.0578 (9)
C9	0.3306 (1)	−0.0621 (3)	0.5471 (5)	0.0820 (8)
C10	0.41475 (9)	0.2521 (3)	0.6311 (3)	0.0555 (9)
C11	0.4228 (1)	0.3618 (3)	0.6944 (4)	0.0650 (7)
C12	0.4427 (1)	0.3705 (4)	0.8347 (4)	0.0740 (8)
C13	0.4540 (1)	0.2705 (4)	0.9143 (4)	0.0760 (8)
C14	0.4460 (1)	0.1589 (4)	0.8499 (4)	0.0780 (8)
C15	0.4264 (1)	0.1493 (3)	0.7085 (4)	0.0680 (7)
C16	0.4755 (1)	0.2785 (5)	1.0680 (5)	0.1180 (9)
H(1)	0.3147	0.3051	0.4412	0.069*
H(2)	0.2519	0.2201	0.3234	0.066*
H(3)	0.1724	0.2085	0.3226	0.079*
H(4)	0.1348	0.1126	0.5232	0.081*
H(5)	0.1754	0.0288	0.7220	0.079*
H(6)	0.2547	0.0372	0.7226	0.069*
H(7)	0.3059	−0.1020	0.5952	0.099*
H(8)	0.3580	−0.1038	0.5688	0.099*
H(9)	0.3258	−0.0603	0.4397	0.099*
H(10)	0.4140	0.4333	0.6383	0.079*
H(11)	0.4490	0.4488	0.8787	0.089*
H(12)	0.4544	0.0870	0.9058	0.094*
H(13)	0.4207	0.0716	0.6619	0.081*
H(14)	0.5076	0.2812	1.0575	0.142*
H(15)	0.4672	0.2107	1.1279	0.142*
H(16)	0.4652	0.3497	1.1169	0.142*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0516 (5)	0.0739 (6)	0.0529 (5)	−0.0062 (4)	0.0023 (3)	0.0018 (4)
O1	0.071 (1)	0.096 (2)	0.072 (2)	0.004 (1)	0.007 (1)	−0.025 (1)
O2	0.068 (1)	0.098 (2)	0.071 (1)	−0.022 (1)	−0.002 (1)	0.026 (1)
O3	0.063 (1)	0.060 (1)	0.070 (1)	−0.004 (1)	−0.018 (1)	0.008 (1)
C1	0.053 (2)	0.061 (2)	0.058 (2)	−0.001 (1)	−0.006 (1)	0.004 (1)
C2	0.056 (2)	0.054 (2)	0.041 (1)	−0.001 (1)	−0.004 (1)	−0.005 (1)
C3	0.055 (2)	0.046 (1)	0.044 (1)	−0.003 (1)	−0.003 (1)	−0.007 (1)
C4	0.064 (2)	0.055 (2)	0.048 (2)	−0.004 (1)	−0.005 (1)	0.001 (1)
C5	0.064 (2)	0.065 (2)	0.069 (2)	−0.001 (2)	−0.019 (2)	0.000 (2)
C6	0.053 (2)	0.071 (2)	0.080 (2)	−0.005 (1)	−0.004 (2)	0.000 (2)
C7	0.065 (2)	0.070 (2)	0.063 (2)	−0.010 (2)	0.009 (2)	−0.001 (2)
C8	0.064 (2)	0.060 (2)	0.050 (2)	−0.008 (1)	−0.006 (1)	0.001 (1)
C9	0.082 (2)	0.059 (2)	0.104 (3)	0.011 (2)	−0.001 (2)	0.002 (2)
C10	0.041 (1)	0.067 (2)	0.058 (2)	−0.003 (1)	0.004 (1)	−0.000 (1)
C11	0.054 (2)	0.072 (2)	0.069 (2)	0.003 (1)	0.003 (2)	−0.006 (2)
C12	0.060 (2)	0.091 (3)	0.071 (2)	−0.002 (2)	0.005 (2)	−0.023 (2)
C13	0.040 (2)	0.130 (3)	0.058 (2)	−0.006 (2)	0.006 (1)	−0.010 (2)
C14	0.056 (2)	0.105 (3)	0.073 (2)	−0.002 (2)	−0.008 (2)	0.028 (2)
C15	0.055 (2)	0.070 (2)	0.077 (2)	−0.004 (1)	−0.007 (2)	0.007 (2)
C16	0.071 (3)	0.226 (6)	0.058 (2)	−0.011 (3)	−0.001 (2)	−0.012 (3)

Geometric parameters (Å, º)

S1—O1	1.433 (3)	C13—C16	1.503 (5)
S1—O2	1.435 (3)	C14—C15	1.383 (5)
S1—C1	1.744 (3)	C1—H(1)	0.9800
S1—C10	1.752 (3)	C4—H(2)	0.9800
O3—C2	1.358 (3)	C5—H(3)	0.9800
O3—C9	1.451 (4)	C6—H(4)	0.9800
C1—C2	1.330 (4)	C7—H(5)	0.9800
C2—C3	1.474 (4)	C8—H(6)	0.9800
C3—C4	1.392 (4)	C9—H(7)	0.9600
C3—C8	1.385 (4)	C9—H(8)	0.9600
C4—C5	1.381 (4)	C9—H(9)	0.9600
C5—C6	1.382 (5)	C11—H(10)	0.9800
C6—C7	1.362 (5)	C12—H(11)	0.9800
C7—C8	1.377 (4)	C14—H(12)	0.9800
C10—C11	1.376 (4)	C15—H(13)	0.9800
C10—C15	1.386 (4)	C16—H(14)	0.9600
C11—C12	1.376 (5)	C16—H(15)	0.9600
C12—C13	1.369 (6)	C16—H(16)	0.9600
C13—C14	1.398 (6)
O2—S1—O1	118.7 (1)	O3—C9—H(9)	109.2333
C1—S1—O1	108.5 (1)	O3—C9—H(7)	109.9719
C10—S1—O1	108.5 (1)	H(1)—C1—C2	117.2450
C1—S1—O2	105.0 (1)	C3—C4—H(2)	119.4624
C10—S1—O2	107.9 (1)	C3—C8—H(6)	119.1416
S1—C1—C2	124.7 (2)	H(2)—C4—C5	119.9248
C10—S1—C1	107.8 (1)	C4—C5—H(3)	120.5313
S1—C10—C11	119.8 (2)	H(3)—C5—C6	119.7407
S1—C10—C15	119.9 (2)	C5—C6—H(4)	119.9117
O3—C2—C1	117.8 (2)	C6—C7—H(5)	119.3413
C9—O3—C2	116.8 (2)	H(4)—C6—C7	119.8786
O3—C2—C3	117.8 (2)	C7—C8—H(6)	119.8779
C1—C2—C3	124.2 (3)	H(5)—C7—C8	120.4354
C2—C3—C8	121.5 (2)	H(8)—C9—H(7)	109.4811
C2—C3—C4	120.2 (2)	H(9)—C9—H(7)	109.4642
C8—C3—C4	118.2 (3)	H(9)—C9—H(8)	109.4764
C3—C4—C5	120.6 (3)	C10—C11—H(10)	118.9288
C3—C8—C7	121.0 (3)	C10—C15—H(13)	119.5625
C4—C5—C6	119.7 (3)	H(10)—C11—C12	120.7847
C5—C6—C7	120.2 (3)	C11—C12—H(11)	120.2567
C6—C7—C8	120.2 (3)	H(11)—C12—C13	119.0773
C15—C10—C11	120.3 (3)	C13—C14—H(12)	119.4312
C10—C11—C12	120.3 (3)	C13—C16—H(14)	109.7170
C10—C15—C14	119.0 (3)	C13—C16—H(15)	109.9732
C11—C12—C13	120.7 (4)	C13—C16—H(16)	108.7141
C12—C13—C14	119.1 (3)	C14—C15—H(13)	121.4238
C12—C13—C16	121.3 (4)	H(12)—C14—C15	119.8925
C13—C14—C15	120.7 (4)	H(15)—C16—H(14)	109.4761
C16—C13—C14	119.6 (4)	H(16)—C16—H(14)	109.4746
S1—C1—H(1)	118.0695	H(16)—C16—H(15)	109.4694
O3—C9—H(8)	109.1991