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In the title compound, C16H18O4S, the dihedral angle between the two aromatic rings is 43.71 (6)°. The mol­ecular structure is stabilized by a weak intra­molecular C–H...O inter­action and the crystal packing is stabilized by weak inter­molecular C—H...O inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680705619X/bt2585sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680705619X/bt2585Isup2.hkl
Contains datablock I

CCDC reference: 672890

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.039
  • wR factor = 0.106
  • Data-to-parameter ratio = 13.8

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............ 24.71 Deg.
Author Response: Since the criterion for MoKa is 25.24 deg and the data parameter ratio for I looks alright, we hope this is not a real problem

Alert level C THETM01_ALERT_3_C The value of sine(theta_max)/wavelength is less than 0.590 Calculated sin(theta_max)/wavelength = 0.5882 PLAT023_ALERT_3_C Resolution (too) Low [sin(th)/Lambda < 0.6]..... 24.71 Deg. PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 200 Deg.
1 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 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 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

Several compounds containing the para-toluene sulfonate moiety are used in the fields of biology and industry. The merging of lipids can be monitored using a derivative of para-toluene sulfonate (Yachi et al., 1989). This method has been used in studying the membrane fusion during the acrosome reaction (Spungin et al., 1984).

The geometric parameters in the title compound (Fig. 1) agree with the reported values of similar structures (Manivannan et al., 2005a; Manivannan et al., 2005b). The dihedral angle between the two phenyl rings is 43.71 (6)°. The ethoxy group is almost coplanar with the benzene ring C18—C13 to which it attached, with the dihedral angle of 4.84 (10)°.

The details of the hydrogen bonding are given in Table 1. The molecular structure is stabilized by a weak intramolecular C—H···O interaction and the crystal packing (Fig. 2) is stabilized by weak intermolecular C—H···O interactions.

Related literature top

For releted literature, see: Manivannan et al. (2005a); Spungin et al. (1984); Yachi et al. (1989). A similar compound has been reported (Manivannan et al., 2005b).

Experimental top

2-ethoxy, 4 methyl phenol (4.9 mmol)(17), triethylamine (4.9 mmol), were dissolved separately in acetone (10 ml) and mixed. To this solution, 4-toluene sulfonyl chloride (3.9 mmol), dissolved in acetone (10 ml) was added. The solution was left overnight and evaporated. The residue obtained was washed several times with 2% aqueous triethylamine solution to obtain the crude product. Crystals were obtained by recrystallizing the crude product (2.6 mmol, 68% yield) from ethanol.

Refinement top

H atoms were positioned geometrically and refined using riding model with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C) for aromatic C—H, C—H = 0.97 Å and Uiso(H) = 1.2Ueq(C) for CH2 and C—H = 0.96 Å and Uiso(H) = 1.5Ueq(C) for CH3.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 (Bruker, 2004); data reduction: APEX2 (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, with atom labels and 50% probability displacement ellipsoids for non-H atoms.
[Figure 2] Fig. 2. The packing of the title compound, viewed down the c axis. Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted.
2-Ethoxy-4-methylphenyl p-toluenesulfonate top
Crystal data top
C16H18O4SZ = 2
Mr = 306.36F(000) = 324
Triclinic, P1Dx = 1.303 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.8095 (10) ÅCell parameters from 2654 reflections
b = 9.2787 (12) Åθ = 1.9–24.7°
c = 11.4058 (15) ŵ = 0.22 mm1
α = 104.678 (2)°T = 295 K
β = 99.653 (2)°Block, colourless
γ = 94.906 (2)°0.48 × 0.46 × 0.14 mm
V = 781.06 (18) Å3
Data collection top
Bruker Kappa APEX)
diffractometer
2654 independent reflections
Radiation source: fine-focus sealed tube2338 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.016
ω and ϕ scanθmax = 24.7°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 99
Tmin = 0.902, Tmax = 0.970k = 1010
7352 measured reflectionsl = 1313
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0551P)2 + 0.2034P]
where P = (Fo2 + 2Fc2)/3
2654 reflections(Δ/σ)max < 0.001
193 parametersΔρmax = 0.21 e Å3
0 restraintsΔρmin = 0.21 e Å3
Crystal data top
C16H18O4Sγ = 94.906 (2)°
Mr = 306.36V = 781.06 (18) Å3
Triclinic, P1Z = 2
a = 7.8095 (10) ÅMo Kα radiation
b = 9.2787 (12) ŵ = 0.22 mm1
c = 11.4058 (15) ÅT = 295 K
α = 104.678 (2)°0.48 × 0.46 × 0.14 mm
β = 99.653 (2)°
Data collection top
Bruker Kappa APEX)
diffractometer
2654 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
2338 reflections with I > 2σ(I)
Tmin = 0.902, Tmax = 0.970Rint = 0.016
7352 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0390 restraints
wR(F2) = 0.107H-atom parameters constrained
S = 1.06Δρmax = 0.21 e Å3
2654 reflectionsΔρmin = 0.21 e Å3
193 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.34100 (7)0.33058 (5)0.26424 (4)0.05261 (18)
O10.52497 (16)0.28192 (14)0.31438 (12)0.0548 (4)
O40.69333 (17)0.21268 (14)0.12633 (12)0.0544 (4)
O30.2656 (2)0.23076 (18)0.14687 (12)0.0674 (4)
O20.3812 (2)0.48652 (17)0.27924 (16)0.0795 (5)
C10.2133 (2)0.3036 (2)0.37126 (16)0.0440 (4)
C130.6426 (2)0.0974 (2)0.17164 (15)0.0435 (4)
C120.6741 (2)0.0497 (2)0.12995 (16)0.0464 (4)
H120.73230.07530.06430.056*
C80.5536 (2)0.1316 (2)0.26945 (16)0.0455 (4)
C90.5040 (2)0.0247 (2)0.32517 (17)0.0538 (5)
H90.44770.05060.39180.065*
C60.0909 (2)0.1766 (2)0.34244 (17)0.0517 (5)
H60.07680.10460.26690.062*
C150.7938 (3)0.1811 (2)0.03069 (18)0.0528 (5)
H15A0.72300.11250.04380.063*
H15B0.89510.13500.05670.063*
C110.6209 (2)0.1601 (2)0.18391 (18)0.0493 (4)
C20.2360 (3)0.4108 (2)0.48349 (17)0.0522 (5)
H20.31870.49580.50240.063*
C40.0098 (3)0.2646 (2)0.54036 (19)0.0559 (5)
C100.5370 (3)0.1207 (2)0.28299 (18)0.0566 (5)
H100.50300.19290.32110.068*
C50.0096 (3)0.1585 (2)0.42711 (19)0.0566 (5)
H50.09220.07350.40810.068*
C30.1343 (3)0.3898 (2)0.56696 (18)0.0611 (5)
H30.14960.46120.64290.073*
C140.6526 (3)0.3197 (2)0.1314 (2)0.0688 (6)
H14A0.59910.38410.17280.103*
H14B0.77640.32450.14320.103*
H14C0.60250.35210.04460.103*
C160.8511 (3)0.3271 (3)0.0064 (2)0.0790 (7)
H16A0.74990.37130.01990.118*
H16B0.91930.30940.05720.118*
H16C0.92080.39410.08070.118*
C70.1038 (4)0.2435 (3)0.6305 (3)0.0897 (8)
H7A0.05480.17890.67720.135*
H7B0.21960.19880.58620.135*
H7C0.10960.33930.68580.135*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0591 (3)0.0523 (3)0.0535 (3)0.0119 (2)0.0268 (2)0.0154 (2)
O10.0466 (7)0.0511 (8)0.0602 (8)0.0028 (6)0.0201 (6)0.0012 (6)
O40.0615 (8)0.0459 (7)0.0635 (8)0.0069 (6)0.0322 (7)0.0160 (6)
O30.0696 (9)0.0892 (11)0.0448 (8)0.0208 (8)0.0181 (7)0.0129 (7)
O20.0996 (12)0.0575 (9)0.1041 (12)0.0188 (8)0.0587 (10)0.0346 (9)
C10.0412 (9)0.0472 (10)0.0467 (10)0.0100 (8)0.0151 (8)0.0127 (8)
C130.0392 (9)0.0470 (10)0.0428 (9)0.0001 (7)0.0108 (7)0.0099 (8)
C120.0465 (10)0.0497 (11)0.0441 (10)0.0059 (8)0.0160 (8)0.0102 (8)
C80.0379 (9)0.0488 (10)0.0459 (10)0.0019 (8)0.0120 (8)0.0047 (8)
C90.0471 (10)0.0686 (13)0.0499 (11)0.0064 (9)0.0212 (8)0.0163 (9)
C60.0513 (11)0.0516 (11)0.0484 (10)0.0031 (8)0.0109 (8)0.0073 (8)
C150.0521 (11)0.0580 (12)0.0553 (11)0.0079 (9)0.0232 (9)0.0196 (9)
C110.0453 (10)0.0488 (11)0.0547 (11)0.0042 (8)0.0110 (8)0.0156 (8)
C20.0546 (11)0.0475 (11)0.0528 (11)0.0027 (8)0.0180 (9)0.0069 (9)
C40.0520 (11)0.0659 (13)0.0631 (12)0.0203 (10)0.0250 (9)0.0287 (10)
C100.0530 (11)0.0627 (13)0.0638 (12)0.0053 (9)0.0218 (10)0.0286 (10)
C50.0427 (10)0.0614 (12)0.0693 (13)0.0023 (9)0.0132 (9)0.0242 (10)
C30.0736 (14)0.0638 (13)0.0479 (11)0.0171 (11)0.0243 (10)0.0080 (9)
C140.0793 (15)0.0508 (12)0.0835 (15)0.0122 (11)0.0262 (12)0.0230 (11)
C160.0830 (17)0.0744 (16)0.0989 (18)0.0104 (12)0.0454 (14)0.0408 (14)
C70.0916 (18)0.109 (2)0.0970 (19)0.0282 (16)0.0599 (16)0.0468 (16)
Geometric parameters (Å, º) top
S1—O21.4143 (16)C15—H15B0.9700
S1—O31.4180 (15)C11—C101.385 (3)
S1—O11.6004 (14)C11—C141.509 (3)
S1—C11.7517 (17)C2—C31.377 (3)
O1—C81.410 (2)C2—H20.9300
O4—C131.358 (2)C4—C31.384 (3)
O4—C151.434 (2)C4—C51.388 (3)
C1—C21.381 (2)C4—C71.504 (3)
C1—C61.384 (3)C10—H100.9300
C13—C121.385 (2)C5—H50.9300
C13—C81.395 (2)C3—H30.9300
C12—C111.390 (3)C14—H14A0.9600
C12—H120.9300C14—H14B0.9600
C8—C91.369 (3)C14—H14C0.9600
C9—C101.375 (3)C16—H16A0.9600
C9—H90.9300C16—H16B0.9600
C6—C51.375 (3)C16—H16C0.9600
C6—H60.9300C7—H7A0.9600
C15—C161.496 (3)C7—H7B0.9600
C15—H15A0.9700C7—H7C0.9600
O2—S1—O3121.17 (10)C12—C11—C14119.16 (17)
O2—S1—O1103.58 (9)C3—C2—C1118.89 (18)
O3—S1—O1109.09 (8)C3—C2—H2120.6
O2—S1—C1109.05 (9)C1—C2—H2120.6
O3—S1—C1108.99 (9)C3—C4—C5118.35 (18)
O1—S1—C1103.46 (8)C3—C4—C7121.4 (2)
C8—O1—S1118.68 (11)C5—C4—C7120.3 (2)
C13—O4—C15117.46 (14)C9—C10—C11120.26 (18)
C2—C1—C6120.97 (17)C9—C10—H10119.9
C2—C1—S1119.08 (14)C11—C10—H10119.9
C6—C1—S1119.95 (14)C6—C5—C4121.28 (19)
O4—C13—C12125.41 (15)C6—C5—H5119.4
O4—C13—C8116.83 (16)C4—C5—H5119.4
C12—C13—C8117.75 (16)C2—C3—C4121.48 (18)
C13—C12—C11121.53 (16)C2—C3—H3119.3
C13—C12—H12119.2C4—C3—H3119.3
C11—C12—H12119.2C11—C14—H14A109.5
C9—C8—C13121.27 (17)C11—C14—H14B109.5
C9—C8—O1120.61 (16)H14A—C14—H14B109.5
C13—C8—O1118.02 (16)C11—C14—H14C109.5
C8—C9—C10120.21 (17)H14A—C14—H14C109.5
C8—C9—H9119.9H14B—C14—H14C109.5
C10—C9—H9119.9C15—C16—H16A109.5
C5—C6—C1119.04 (18)C15—C16—H16B109.5
C5—C6—H6120.5H16A—C16—H16B109.5
C1—C6—H6120.5C15—C16—H16C109.5
O4—C15—C16107.62 (16)H16A—C16—H16C109.5
O4—C15—H15A110.2H16B—C16—H16C109.5
C16—C15—H15A110.2C4—C7—H7A109.5
O4—C15—H15B110.2C4—C7—H7B109.5
C16—C15—H15B110.2H7A—C7—H7B109.5
H15A—C15—H15B108.5C4—C7—H7C109.5
C10—C11—C12118.93 (17)H7A—C7—H7C109.5
C10—C11—C14121.89 (18)H7B—C7—H7C109.5
O2—S1—O1—C8154.33 (13)C13—C8—C9—C101.9 (3)
O3—S1—O1—C824.01 (15)O1—C8—C9—C10178.07 (17)
C1—S1—O1—C891.91 (13)C2—C1—C6—C50.4 (3)
O2—S1—C1—C230.49 (18)S1—C1—C6—C5179.20 (14)
O3—S1—C1—C2164.75 (15)C13—O4—C15—C16173.64 (17)
O1—S1—C1—C279.27 (16)C13—C12—C11—C101.1 (3)
O2—S1—C1—C6149.11 (16)C13—C12—C11—C14177.62 (18)
O3—S1—C1—C614.85 (18)C6—C1—C2—C30.1 (3)
O1—S1—C1—C6101.13 (16)S1—C1—C2—C3179.48 (15)
C15—O4—C13—C122.6 (3)C8—C9—C10—C110.1 (3)
C15—O4—C13—C8176.46 (16)C12—C11—C10—C91.4 (3)
O4—C13—C12—C11178.42 (16)C14—C11—C10—C9177.30 (19)
C8—C13—C12—C110.6 (3)C1—C6—C5—C40.1 (3)
O4—C13—C8—C9177.01 (16)C3—C4—C5—C60.4 (3)
C12—C13—C8—C92.1 (3)C7—C4—C5—C6179.0 (2)
O4—C13—C8—O10.7 (2)C1—C2—C3—C40.4 (3)
C12—C13—C8—O1178.41 (15)C5—C4—C3—C20.7 (3)
S1—O1—C8—C987.46 (19)C7—C4—C3—C2178.7 (2)
S1—O1—C8—C1396.20 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6—H6···O30.932.572.926 (2)103
C2—H2···O1i0.932.583.353 (2)141
C12—H12···O3ii0.932.483.310 (2)149
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+1, y, z.

Experimental details

Crystal data
Chemical formulaC16H18O4S
Mr306.36
Crystal system, space groupTriclinic, P1
Temperature (K)295
a, b, c (Å)7.8095 (10), 9.2787 (12), 11.4058 (15)
α, β, γ (°)104.678 (2), 99.653 (2), 94.906 (2)
V3)781.06 (18)
Z2
Radiation typeMo Kα
µ (mm1)0.22
Crystal size (mm)0.48 × 0.46 × 0.14
Data collection
DiffractometerBruker Kappa APEX)
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.902, 0.970
No. of measured, independent and
observed [I > 2σ(I)] reflections
7352, 2654, 2338
Rint0.016
(sin θ/λ)max1)0.588
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.039, 0.107, 1.06
No. of reflections2654
No. of parameters193
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.21, 0.21

Computer programs: APEX2 (Bruker, 2004), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6—H6···O30.932.572.926 (2)103
C2—H2···O1i0.932.583.353 (2)141
C12—H12···O3ii0.932.483.310 (2)149
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+1, y, z.
 

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