Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680705619X/bt2585sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680705619X/bt2585Isup2.hkl |
CCDC reference: 672890
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (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
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).
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.
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.
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).
C16H18O4S | Z = 2 |
Mr = 306.36 | F(000) = 324 |
Triclinic, P1 | Dx = 1.303 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.8095 (10) Å | Cell parameters from 2654 reflections |
b = 9.2787 (12) Å | θ = 1.9–24.7° |
c = 11.4058 (15) Å | µ = 0.22 mm−1 |
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 |
Bruker Kappa APEX) diffractometer | 2654 independent reflections |
Radiation source: fine-focus sealed tube | 2338 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.016 |
ω and ϕ scan | θmax = 24.7°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −9→9 |
Tmin = 0.902, Tmax = 0.970 | k = −10→10 |
7352 measured reflections | l = −13→13 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.107 | H-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 parameters | Δρmax = 0.21 e Å−3 |
0 restraints | Δρmin = −0.21 e Å−3 |
C16H18O4S | γ = 94.906 (2)° |
Mr = 306.36 | V = 781.06 (18) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.8095 (10) Å | Mo Kα radiation |
b = 9.2787 (12) Å | µ = 0.22 mm−1 |
c = 11.4058 (15) Å | T = 295 K |
α = 104.678 (2)° | 0.48 × 0.46 × 0.14 mm |
β = 99.653 (2)° |
Bruker Kappa APEX) diffractometer | 2654 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2338 reflections with I > 2σ(I) |
Tmin = 0.902, Tmax = 0.970 | Rint = 0.016 |
7352 measured reflections |
R[F2 > 2σ(F2)] = 0.039 | 0 restraints |
wR(F2) = 0.107 | H-atom parameters constrained |
S = 1.06 | Δρmax = 0.21 e Å−3 |
2654 reflections | Δρmin = −0.21 e Å−3 |
193 parameters |
x | y | z | Uiso*/Ueq | ||
S1 | 0.34100 (7) | 0.33058 (5) | 0.26424 (4) | 0.05261 (18) | |
O1 | 0.52497 (16) | 0.28192 (14) | 0.31438 (12) | 0.0548 (4) | |
O4 | 0.69333 (17) | 0.21268 (14) | 0.12633 (12) | 0.0544 (4) | |
O3 | 0.2656 (2) | 0.23076 (18) | 0.14687 (12) | 0.0674 (4) | |
O2 | 0.3812 (2) | 0.48652 (17) | 0.27924 (16) | 0.0795 (5) | |
C1 | 0.2133 (2) | 0.3036 (2) | 0.37126 (16) | 0.0440 (4) | |
C13 | 0.6426 (2) | 0.0974 (2) | 0.17164 (15) | 0.0435 (4) | |
C12 | 0.6741 (2) | −0.0497 (2) | 0.12995 (16) | 0.0464 (4) | |
H12 | 0.7323 | −0.0753 | 0.0643 | 0.056* | |
C8 | 0.5536 (2) | 0.1316 (2) | 0.26945 (16) | 0.0455 (4) | |
C9 | 0.5040 (2) | 0.0247 (2) | 0.32517 (17) | 0.0538 (5) | |
H9 | 0.4477 | 0.0506 | 0.3918 | 0.065* | |
C6 | 0.0909 (2) | 0.1766 (2) | 0.34244 (17) | 0.0517 (5) | |
H6 | 0.0768 | 0.1046 | 0.2669 | 0.062* | |
C15 | 0.7938 (3) | 0.1811 (2) | 0.03069 (18) | 0.0528 (5) | |
H15A | 0.7230 | 0.1125 | −0.0438 | 0.063* | |
H15B | 0.8951 | 0.1350 | 0.0567 | 0.063* | |
C11 | 0.6209 (2) | −0.1601 (2) | 0.18391 (18) | 0.0493 (4) | |
C2 | 0.2360 (3) | 0.4108 (2) | 0.48349 (17) | 0.0522 (5) | |
H2 | 0.3187 | 0.4958 | 0.5024 | 0.063* | |
C4 | 0.0098 (3) | 0.2646 (2) | 0.54036 (19) | 0.0559 (5) | |
C10 | 0.5370 (3) | −0.1207 (2) | 0.28299 (18) | 0.0566 (5) | |
H10 | 0.5030 | −0.1929 | 0.3211 | 0.068* | |
C5 | −0.0096 (3) | 0.1585 (2) | 0.42711 (19) | 0.0566 (5) | |
H5 | −0.0922 | 0.0735 | 0.4081 | 0.068* | |
C3 | 0.1343 (3) | 0.3898 (2) | 0.56696 (18) | 0.0611 (5) | |
H3 | 0.1496 | 0.4612 | 0.6429 | 0.073* | |
C14 | 0.6526 (3) | −0.3197 (2) | 0.1314 (2) | 0.0688 (6) | |
H14A | 0.5991 | −0.3841 | 0.1728 | 0.103* | |
H14B | 0.7764 | −0.3245 | 0.1432 | 0.103* | |
H14C | 0.6025 | −0.3521 | 0.0446 | 0.103* | |
C16 | 0.8511 (3) | 0.3271 (3) | 0.0064 (2) | 0.0790 (7) | |
H16A | 0.7499 | 0.3713 | −0.0199 | 0.118* | |
H16B | 0.9193 | 0.3094 | −0.0572 | 0.118* | |
H16C | 0.9208 | 0.3941 | 0.0807 | 0.118* | |
C7 | −0.1038 (4) | 0.2435 (3) | 0.6305 (3) | 0.0897 (8) | |
H7A | −0.0548 | 0.1789 | 0.6772 | 0.135* | |
H7B | −0.2196 | 0.1988 | 0.5862 | 0.135* | |
H7C | −0.1096 | 0.3393 | 0.6858 | 0.135* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0591 (3) | 0.0523 (3) | 0.0535 (3) | 0.0119 (2) | 0.0268 (2) | 0.0154 (2) |
O1 | 0.0466 (7) | 0.0511 (8) | 0.0602 (8) | 0.0028 (6) | 0.0201 (6) | −0.0012 (6) |
O4 | 0.0615 (8) | 0.0459 (7) | 0.0635 (8) | 0.0069 (6) | 0.0322 (7) | 0.0160 (6) |
O3 | 0.0696 (9) | 0.0892 (11) | 0.0448 (8) | 0.0208 (8) | 0.0181 (7) | 0.0129 (7) |
O2 | 0.0996 (12) | 0.0575 (9) | 0.1041 (12) | 0.0188 (8) | 0.0587 (10) | 0.0346 (9) |
C1 | 0.0412 (9) | 0.0472 (10) | 0.0467 (10) | 0.0100 (8) | 0.0151 (8) | 0.0127 (8) |
C13 | 0.0392 (9) | 0.0470 (10) | 0.0428 (9) | 0.0001 (7) | 0.0108 (7) | 0.0099 (8) |
C12 | 0.0465 (10) | 0.0497 (11) | 0.0441 (10) | 0.0059 (8) | 0.0160 (8) | 0.0102 (8) |
C8 | 0.0379 (9) | 0.0488 (10) | 0.0459 (10) | 0.0019 (8) | 0.0120 (8) | 0.0047 (8) |
C9 | 0.0471 (10) | 0.0686 (13) | 0.0499 (11) | 0.0064 (9) | 0.0212 (8) | 0.0163 (9) |
C6 | 0.0513 (11) | 0.0516 (11) | 0.0484 (10) | 0.0031 (8) | 0.0109 (8) | 0.0073 (8) |
C15 | 0.0521 (11) | 0.0580 (12) | 0.0553 (11) | 0.0079 (9) | 0.0232 (9) | 0.0196 (9) |
C11 | 0.0453 (10) | 0.0488 (11) | 0.0547 (11) | 0.0042 (8) | 0.0110 (8) | 0.0156 (8) |
C2 | 0.0546 (11) | 0.0475 (11) | 0.0528 (11) | 0.0027 (8) | 0.0180 (9) | 0.0069 (9) |
C4 | 0.0520 (11) | 0.0659 (13) | 0.0631 (12) | 0.0203 (10) | 0.0250 (9) | 0.0287 (10) |
C10 | 0.0530 (11) | 0.0627 (13) | 0.0638 (12) | 0.0053 (9) | 0.0218 (10) | 0.0286 (10) |
C5 | 0.0427 (10) | 0.0614 (12) | 0.0693 (13) | 0.0023 (9) | 0.0132 (9) | 0.0242 (10) |
C3 | 0.0736 (14) | 0.0638 (13) | 0.0479 (11) | 0.0171 (11) | 0.0243 (10) | 0.0080 (9) |
C14 | 0.0793 (15) | 0.0508 (12) | 0.0835 (15) | 0.0122 (11) | 0.0262 (12) | 0.0230 (11) |
C16 | 0.0830 (17) | 0.0744 (16) | 0.0989 (18) | 0.0104 (12) | 0.0454 (14) | 0.0408 (14) |
C7 | 0.0916 (18) | 0.109 (2) | 0.0970 (19) | 0.0282 (16) | 0.0599 (16) | 0.0468 (16) |
S1—O2 | 1.4143 (16) | C15—H15B | 0.9700 |
S1—O3 | 1.4180 (15) | C11—C10 | 1.385 (3) |
S1—O1 | 1.6004 (14) | C11—C14 | 1.509 (3) |
S1—C1 | 1.7517 (17) | C2—C3 | 1.377 (3) |
O1—C8 | 1.410 (2) | C2—H2 | 0.9300 |
O4—C13 | 1.358 (2) | C4—C3 | 1.384 (3) |
O4—C15 | 1.434 (2) | C4—C5 | 1.388 (3) |
C1—C2 | 1.381 (2) | C4—C7 | 1.504 (3) |
C1—C6 | 1.384 (3) | C10—H10 | 0.9300 |
C13—C12 | 1.385 (2) | C5—H5 | 0.9300 |
C13—C8 | 1.395 (2) | C3—H3 | 0.9300 |
C12—C11 | 1.390 (3) | C14—H14A | 0.9600 |
C12—H12 | 0.9300 | C14—H14B | 0.9600 |
C8—C9 | 1.369 (3) | C14—H14C | 0.9600 |
C9—C10 | 1.375 (3) | C16—H16A | 0.9600 |
C9—H9 | 0.9300 | C16—H16B | 0.9600 |
C6—C5 | 1.375 (3) | C16—H16C | 0.9600 |
C6—H6 | 0.9300 | C7—H7A | 0.9600 |
C15—C16 | 1.496 (3) | C7—H7B | 0.9600 |
C15—H15A | 0.9700 | C7—H7C | 0.9600 |
O2—S1—O3 | 121.17 (10) | C12—C11—C14 | 119.16 (17) |
O2—S1—O1 | 103.58 (9) | C3—C2—C1 | 118.89 (18) |
O3—S1—O1 | 109.09 (8) | C3—C2—H2 | 120.6 |
O2—S1—C1 | 109.05 (9) | C1—C2—H2 | 120.6 |
O3—S1—C1 | 108.99 (9) | C3—C4—C5 | 118.35 (18) |
O1—S1—C1 | 103.46 (8) | C3—C4—C7 | 121.4 (2) |
C8—O1—S1 | 118.68 (11) | C5—C4—C7 | 120.3 (2) |
C13—O4—C15 | 117.46 (14) | C9—C10—C11 | 120.26 (18) |
C2—C1—C6 | 120.97 (17) | C9—C10—H10 | 119.9 |
C2—C1—S1 | 119.08 (14) | C11—C10—H10 | 119.9 |
C6—C1—S1 | 119.95 (14) | C6—C5—C4 | 121.28 (19) |
O4—C13—C12 | 125.41 (15) | C6—C5—H5 | 119.4 |
O4—C13—C8 | 116.83 (16) | C4—C5—H5 | 119.4 |
C12—C13—C8 | 117.75 (16) | C2—C3—C4 | 121.48 (18) |
C13—C12—C11 | 121.53 (16) | C2—C3—H3 | 119.3 |
C13—C12—H12 | 119.2 | C4—C3—H3 | 119.3 |
C11—C12—H12 | 119.2 | C11—C14—H14A | 109.5 |
C9—C8—C13 | 121.27 (17) | C11—C14—H14B | 109.5 |
C9—C8—O1 | 120.61 (16) | H14A—C14—H14B | 109.5 |
C13—C8—O1 | 118.02 (16) | C11—C14—H14C | 109.5 |
C8—C9—C10 | 120.21 (17) | H14A—C14—H14C | 109.5 |
C8—C9—H9 | 119.9 | H14B—C14—H14C | 109.5 |
C10—C9—H9 | 119.9 | C15—C16—H16A | 109.5 |
C5—C6—C1 | 119.04 (18) | C15—C16—H16B | 109.5 |
C5—C6—H6 | 120.5 | H16A—C16—H16B | 109.5 |
C1—C6—H6 | 120.5 | C15—C16—H16C | 109.5 |
O4—C15—C16 | 107.62 (16) | H16A—C16—H16C | 109.5 |
O4—C15—H15A | 110.2 | H16B—C16—H16C | 109.5 |
C16—C15—H15A | 110.2 | C4—C7—H7A | 109.5 |
O4—C15—H15B | 110.2 | C4—C7—H7B | 109.5 |
C16—C15—H15B | 110.2 | H7A—C7—H7B | 109.5 |
H15A—C15—H15B | 108.5 | C4—C7—H7C | 109.5 |
C10—C11—C12 | 118.93 (17) | H7A—C7—H7C | 109.5 |
C10—C11—C14 | 121.89 (18) | H7B—C7—H7C | 109.5 |
O2—S1—O1—C8 | −154.33 (13) | C13—C8—C9—C10 | −1.9 (3) |
O3—S1—O1—C8 | −24.01 (15) | O1—C8—C9—C10 | −178.07 (17) |
C1—S1—O1—C8 | 91.91 (13) | C2—C1—C6—C5 | 0.4 (3) |
O2—S1—C1—C2 | −30.49 (18) | S1—C1—C6—C5 | −179.20 (14) |
O3—S1—C1—C2 | −164.75 (15) | C13—O4—C15—C16 | −173.64 (17) |
O1—S1—C1—C2 | 79.27 (16) | C13—C12—C11—C10 | −1.1 (3) |
O2—S1—C1—C6 | 149.11 (16) | C13—C12—C11—C14 | 177.62 (18) |
O3—S1—C1—C6 | 14.85 (18) | C6—C1—C2—C3 | −0.1 (3) |
O1—S1—C1—C6 | −101.13 (16) | S1—C1—C2—C3 | 179.48 (15) |
C15—O4—C13—C12 | −2.6 (3) | C8—C9—C10—C11 | 0.1 (3) |
C15—O4—C13—C8 | 176.46 (16) | C12—C11—C10—C9 | 1.4 (3) |
O4—C13—C12—C11 | 178.42 (16) | C14—C11—C10—C9 | −177.30 (19) |
C8—C13—C12—C11 | −0.6 (3) | C1—C6—C5—C4 | −0.1 (3) |
O4—C13—C8—C9 | −177.01 (16) | C3—C4—C5—C6 | −0.4 (3) |
C12—C13—C8—C9 | 2.1 (3) | C7—C4—C5—C6 | 179.0 (2) |
O4—C13—C8—O1 | −0.7 (2) | C1—C2—C3—C4 | −0.4 (3) |
C12—C13—C8—O1 | 178.41 (15) | C5—C4—C3—C2 | 0.7 (3) |
S1—O1—C8—C9 | −87.46 (19) | C7—C4—C3—C2 | −178.7 (2) |
S1—O1—C8—C13 | 96.20 (16) |
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6···O3 | 0.93 | 2.57 | 2.926 (2) | 103 |
C2—H2···O1i | 0.93 | 2.58 | 3.353 (2) | 141 |
C12—H12···O3ii | 0.93 | 2.48 | 3.310 (2) | 149 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y, −z. |
Experimental details
Crystal data | |
Chemical formula | C16H18O4S |
Mr | 306.36 |
Crystal system, space group | Triclinic, 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) |
V (Å3) | 781.06 (18) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.22 |
Crystal size (mm) | 0.48 × 0.46 × 0.14 |
Data collection | |
Diffractometer | Bruker Kappa APEX) diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.902, 0.970 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7352, 2654, 2338 |
Rint | 0.016 |
(sin θ/λ)max (Å−1) | 0.588 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.039, 0.107, 1.06 |
No. of reflections | 2654 |
No. of parameters | 193 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.21, −0.21 |
Computer programs: APEX2 (Bruker, 2004), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6···O3 | 0.93 | 2.57 | 2.926 (2) | 103 |
C2—H2···O1i | 0.93 | 2.58 | 3.353 (2) | 141 |
C12—H12···O3ii | 0.93 | 2.48 | 3.310 (2) | 149 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y, −z. |
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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.