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Acta Crystallogr Sect E Struct Rep Online. 2010 February 1; 66(Pt 2): o283.
Published online 2010 January 9. doi:  10.1107/S1600536809055329
PMCID: PMC2979761

2-(2,3-Difluoro­phen­yl)ethyl toluene-4-sulfonate

Abstract

In the title compound, C15H14F2O3S, the dihedral angle between the aromatic rings is 6.19 (13)°. In the crystal, mol­ecules are linked by C—H(...)O hydrogen bonds, generating [110] chains.

Related literature

For related structures, see: Zhang & Zang (2008 [triangle]); Xi et al. (2008 [triangle]); Wang & Qin (2008 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0o283-scheme1.jpg

Experimental

Crystal data

  • C15H14F2O3S
  • M r = 312.32
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0o283-efi1.jpg
  • a = 7.487 (12) Å
  • b = 8.386 (14) Å
  • c = 12.69 (2) Å
  • α = 91.67 (3)°
  • β = 96.51 (3)°
  • γ = 105.65 (3)°
  • V = 761 (2) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.24 mm−1
  • T = 295 K
  • 0.21 × 0.21 × 0.16 mm

Data collection

  • Bruker APEXII CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2003 [triangle]) T min = 0.955, T max = 0.966
  • 4133 measured reflections
  • 2630 independent reflections
  • 2246 reflections with I > 2σ(I)
  • R int = 0.018

Refinement

  • R[F 2 > 2σ(F 2)] = 0.046
  • wR(F 2) = 0.180
  • S = 1.10
  • 2630 reflections
  • 191 parameters
  • H-atom parameters constrained
  • Δρmax = 0.35 e Å−3
  • Δρmin = −0.25 e Å−3

Data collection: APEX2 (Bruker, 2003 [triangle]); cell refinement: SAINT (Bruker, 2003 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809055329/hb5283sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809055329/hb5283Isup2.hkl

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

Acknowledgments

The authors are grateful to Jiangsu Polytechnic University and the Natural Science Foundation of China (No.20872051) for financial support.

supplementary crystallographic information

Comment

Toluene-4-sulfonic acid 2-(2,3-difluoro-phenyl)-ethyl ester is an important intermediate for the synthesis of natural products. We have already synthesized and reported several related structures (Zhang et al.,2008; Xi et al.,2008; Wang et al.2008). In this research we report the X-ray crystal structure of the title compound, (I).

In the structure, the dihedral angle between the benzene(C1—C6) and benzene(C9—C14) ring is 6.18°. Weak intermolecular C–H···O hydrogen bonds and C–F···F interactions contribute to the crystal packing.

Experimental

A solution of 2-(2,3-difluoro-phenyl)-ethanol (5 g, 32 mmol) in pyridine (15 ml) was added slowly (in 1 h) to a solution of p-toluenesulfonyl chloride (7.23 g, 38 mmol) in pyridine (17 ml) in ice bath. After being stirred for 3 h in ice bath, The solvent was evaporated on a rotary evaporator and the resulting solid was recrystallized in methanol, yielding the title compound (7.5 g, 76%). Colourless blocks of (I) were grown in methanol by slow evaporation at room temperature.

Refinement

All H atoms were fixed geometrically and treated as riding with C—H = 0.93 Å, 0.96 Å or 0.97 Å, and Uiso(H)=1.2Ueq(C-methylene,C-aromatic) or 1.5Ueq(C-methyl).

Figures

Fig. 1.
The molecular structure of (I) with displacement ellipsoids drawn at the 30% probability level and H atoms represented as spheres of arbitrary radius.

Crystal data

C15H14F2O3SZ = 2
Mr = 312.32F(000) = 324
Triclinic, P1Dx = 1.363 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.487 (12) ÅCell parameters from 2108 reflections
b = 8.386 (14) Åθ = 2.5–26.9°
c = 12.69 (2) ŵ = 0.24 mm1
α = 91.67 (3)°T = 295 K
β = 96.51 (3)°Block, colorless
γ = 105.65 (3)°0.21 × 0.21 × 0.16 mm
V = 761 (2) Å3

Data collection

Bruker APEXII CCD diffractometer2630 independent reflections
Radiation source: fine-focus sealed tube2246 reflections with I > 2σ(I)
graphiteRint = 0.018
[var phi] and ω scansθmax = 25.0°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2003)h = −8→8
Tmin = 0.955, Tmax = 0.966k = −9→7
4133 measured reflectionsl = −14→15

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.180H-atom parameters constrained
S = 1.10w = 1/[σ2(Fo2) + (0.125P)2 + 0.1095P] where P = (Fo2 + 2Fc2)/3
2630 reflections(Δ/σ)max < 0.001
191 parametersΔρmax = 0.35 e Å3
0 restraintsΔρmin = −0.25 e Å3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
S11.10764 (8)0.91567 (7)0.72239 (5)0.0436 (3)
F10.7545 (3)0.2961 (2)1.01476 (15)0.0728 (6)
F20.8697 (2)0.6359 (2)1.04849 (14)0.0664 (5)
O11.3018 (3)0.9177 (3)0.75887 (18)0.0631 (6)
O21.0724 (3)1.0423 (2)0.65329 (16)0.0631 (6)
O31.0172 (2)0.9271 (2)0.83135 (14)0.0489 (5)
C10.5485 (4)0.3112 (3)0.8590 (2)0.0493 (6)
H10.51080.19620.84870.059*
C20.6824 (4)0.3906 (3)0.9445 (2)0.0474 (6)
C30.7407 (3)0.5666 (3)0.96112 (19)0.0429 (6)
C40.6655 (3)0.6682 (3)0.8921 (2)0.0430 (6)
C50.5301 (4)0.5870 (3)0.8060 (2)0.0498 (6)
H50.47800.65080.75970.060*
C60.4721 (4)0.4123 (4)0.7884 (2)0.0542 (7)
H60.38410.36330.73080.065*
C70.7222 (4)0.8606 (3)0.9135 (2)0.0525 (7)
H7A0.80200.88990.98080.063*
H7B0.61050.89610.91950.063*
C80.8273 (4)0.9564 (3)0.8242 (2)0.0532 (7)
H8A0.75790.91640.75490.064*
H8B0.83921.07410.83400.064*
C90.9802 (3)0.7116 (3)0.66443 (19)0.0369 (5)
C101.0027 (4)0.5709 (3)0.7179 (2)0.0430 (6)
H101.08350.58370.78080.052*
C110.9002 (4)0.4104 (3)0.6741 (2)0.0479 (6)
H110.91610.31800.70860.057*
C120.7747 (3)0.3873 (3)0.5795 (2)0.0469 (6)
C130.7558 (4)0.5309 (3)0.5248 (2)0.0511 (7)
H130.67630.51790.46140.061*
C140.8594 (4)0.6939 (3)0.5678 (2)0.0466 (6)
H140.84750.78700.53270.056*
C150.6567 (5)0.2110 (4)0.5350 (3)0.0740 (10)
H15A0.73620.13830.53460.111*
H15B0.60070.21680.46380.111*
H15C0.56050.16910.57910.111*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0463 (4)0.0295 (4)0.0505 (4)0.0020 (3)0.0082 (3)0.0014 (3)
F10.0742 (12)0.0693 (12)0.0839 (13)0.0319 (10)0.0117 (10)0.0265 (10)
F20.0549 (10)0.0767 (12)0.0594 (11)0.0096 (8)−0.0050 (8)−0.0008 (8)
O10.0448 (11)0.0510 (11)0.0832 (15)−0.0004 (8)0.0024 (10)−0.0082 (10)
O20.0868 (15)0.0357 (10)0.0659 (13)0.0110 (10)0.0173 (11)0.0143 (9)
O30.0545 (11)0.0423 (10)0.0471 (11)0.0101 (8)0.0038 (8)−0.0037 (8)
C10.0527 (15)0.0376 (13)0.0559 (16)0.0057 (11)0.0167 (12)−0.0006 (11)
C20.0452 (14)0.0464 (14)0.0560 (16)0.0165 (11)0.0175 (12)0.0132 (12)
C30.0356 (12)0.0515 (15)0.0402 (13)0.0084 (10)0.0077 (10)−0.0008 (11)
C40.0425 (13)0.0397 (14)0.0476 (14)0.0089 (11)0.0146 (11)0.0023 (10)
C50.0528 (15)0.0511 (15)0.0471 (15)0.0172 (12)0.0047 (11)0.0066 (12)
C60.0501 (15)0.0521 (16)0.0532 (16)0.0031 (12)0.0050 (12)−0.0047 (13)
C70.0617 (16)0.0400 (14)0.0580 (16)0.0141 (12)0.0180 (13)−0.0007 (12)
C80.0637 (17)0.0395 (14)0.0618 (17)0.0203 (12)0.0148 (13)0.0060 (12)
C90.0366 (12)0.0320 (12)0.0403 (12)0.0058 (9)0.0061 (10)0.0011 (9)
C100.0458 (13)0.0388 (13)0.0423 (13)0.0100 (10)0.0011 (10)0.0026 (10)
C110.0543 (15)0.0329 (13)0.0562 (16)0.0106 (11)0.0088 (12)0.0051 (11)
C120.0420 (13)0.0414 (14)0.0531 (15)0.0025 (11)0.0133 (11)−0.0085 (11)
C130.0456 (14)0.0582 (16)0.0414 (14)0.0036 (12)−0.0004 (11)−0.0042 (12)
C140.0523 (14)0.0442 (14)0.0415 (13)0.0109 (11)0.0033 (11)0.0076 (10)
C150.072 (2)0.0494 (17)0.084 (2)−0.0101 (15)0.0149 (17)−0.0241 (16)

Geometric parameters (Å, °)

S1—O21.456 (3)C7—H7A0.9700
S1—O11.470 (3)C7—H7B0.9700
S1—O31.618 (3)C8—H8A0.9700
S1—C91.808 (3)C8—H8B0.9700
F1—C21.369 (3)C9—C141.417 (4)
F2—C31.384 (3)C9—C101.417 (4)
O3—C81.500 (4)C10—C111.418 (4)
C1—C21.406 (4)C10—H100.9300
C1—C61.428 (4)C11—C121.412 (4)
C1—H10.9300C11—H110.9300
C2—C31.423 (5)C12—C131.438 (4)
C3—C41.414 (4)C12—C151.555 (4)
C4—C51.421 (4)C13—C141.434 (4)
C4—C71.561 (4)C13—H130.9300
C5—C61.414 (5)C14—H140.9300
C5—H50.9300C15—H15A0.9600
C6—H60.9300C15—H15B0.9600
C7—C81.569 (4)C15—H15C0.9600
O2—S1—O1119.16 (13)O3—C8—C7108.0 (2)
O2—S1—O3109.80 (14)O3—C8—H8A110.1
O1—S1—O3103.90 (15)C7—C8—H8A110.1
O2—S1—C9110.16 (16)O3—C8—H8B110.1
O1—S1—C9109.48 (13)C7—C8—H8B110.1
O3—S1—C9103.00 (12)H8A—C8—H8B108.4
C8—O3—S1118.26 (17)C14—C9—C10121.1 (2)
C2—C1—C6118.1 (3)C14—C9—S1120.24 (19)
C2—C1—H1121.0C10—C9—S1118.7 (2)
C6—C1—H1121.0C9—C10—C11119.0 (2)
F1—C2—C1119.1 (3)C9—C10—H10120.5
F1—C2—C3119.5 (3)C11—C10—H10120.5
C1—C2—C3121.4 (2)C12—C11—C10121.8 (2)
F2—C3—C4120.7 (3)C12—C11—H11119.1
F2—C3—C2118.2 (2)C10—C11—H11119.1
C4—C3—C2121.1 (3)C11—C12—C13118.7 (2)
C3—C4—C5117.1 (3)C11—C12—C15121.2 (3)
C3—C4—C7121.1 (2)C13—C12—C15120.1 (3)
C5—C4—C7121.7 (2)C14—C13—C12120.2 (3)
C6—C5—C4122.2 (3)C14—C13—H13119.9
C6—C5—H5118.9C12—C13—H13119.9
C4—C5—H5118.9C9—C14—C13119.2 (2)
C5—C6—C1120.1 (3)C9—C14—H14120.4
C5—C6—H6120.0C13—C14—H14120.4
C1—C6—H6120.0C12—C15—H15A109.5
C4—C7—C8113.2 (2)C12—C15—H15B109.5
C4—C7—H7A108.9H15A—C15—H15B109.5
C8—C7—H7A108.9C12—C15—H15C109.5
C4—C7—H7B108.9H15A—C15—H15C109.5
C8—C7—H7B108.9H15B—C15—H15C109.5
H7A—C7—H7B107.7
O2—S1—O3—C841.5 (2)S1—O3—C8—C7146.04 (19)
O1—S1—O3—C8170.02 (17)C4—C7—C8—O3−70.1 (3)
C9—S1—O3—C8−75.8 (2)O2—S1—C9—C14−3.1 (2)
C6—C1—C2—F1178.5 (2)O1—S1—C9—C14−136.0 (2)
C6—C1—C2—C30.1 (4)O3—S1—C9—C14114.0 (2)
F1—C2—C3—F20.1 (3)O2—S1—C9—C10177.34 (18)
C1—C2—C3—F2178.4 (2)O1—S1—C9—C1044.5 (2)
F1—C2—C3—C4−178.1 (2)O3—S1—C9—C10−65.6 (2)
C1—C2—C3—C40.2 (4)C14—C9—C10—C11−0.9 (4)
F2—C3—C4—C5−178.3 (2)S1—C9—C10—C11178.70 (19)
C2—C3—C4—C5−0.1 (3)C9—C10—C11—C12−0.9 (4)
F2—C3—C4—C7−1.2 (3)C10—C11—C12—C132.1 (4)
C2—C3—C4—C7177.0 (2)C10—C11—C12—C15−177.3 (2)
C3—C4—C5—C6−0.3 (4)C11—C12—C13—C14−1.7 (4)
C7—C4—C5—C6−177.4 (2)C15—C12—C13—C14177.7 (2)
C4—C5—C6—C10.6 (4)C10—C9—C14—C131.2 (4)
C2—C1—C6—C5−0.5 (4)S1—C9—C14—C13−178.31 (18)
C3—C4—C7—C8116.4 (3)C12—C13—C14—C90.0 (4)
C5—C4—C7—C8−66.7 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C1—H1···O1i0.932.583.442 (7)154

Symmetry codes: (i) x−1, y−1, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5283).

References

  • Bruker (2003). APEX2, SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Wang, Q. & Qin, H. (2008). Chin. J. Chem. Ind. Eng 25, 271–272.
  • Xi, H., Gao, Y., Sun, X., Meng, Q. & Jiang, Y. (2008). Acta Cryst. E64, o1853. [PMC free article] [PubMed]
  • Zhang, C. & Zang, Y. (2008). Chin. J. Organo-Fluorine Ind 2, 48–50.

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