Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803010444/ob6243sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803010444/ob6243Isup2.hkl |
CCDC reference: 214837
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.003 Å
- R factor = 0.058
- wR factor = 0.128
- Data-to-parameter ratio = 13.0
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level C:
ABSTM_02 Alert C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.736 0.974 Tmin' and Tmax expected: 0.900 0.974 RR' = 0.818 Please check that your absorption correction is appropriate.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check
4-Toluenesulfonyl chloride (4.7 mmol) dissolved in acetone (4 ml) was added dropwise to 4-methoxyphenol (4 mmol) in aqueous NaOH (2.5 ml, 10%) with vigorous shaking. The precipitated 4-methoxyphenyl 4-toluenesulfonate (2.7 mmol, yield 67%) was filtered off and recrystallized from diethyl ether.
All the H atoms were located in the difference Fourier map and their positional coordinates and isotropic displacement paramaters were refined. The C—H bond lengths are in the range 0.89 (3)–0.99 (3) Å, the H—C—H angles for the methyl group are in the range 98 (3)–112 (2)° and the C—C—H angles for the aromatic rings are in the range 118.1 (2)–121.9 (2)°.
Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1998); software used to prepare material for publication: SHELXTL.
C14H14O4S | Dx = 1.439 Mg m−3 |
Mr = 278.31 | Melting point = 72–73 K |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 14.778 (5) Å | Cell parameters from 5896 reflections |
b = 5.6665 (18) Å | θ = 2.6–27.6° |
c = 16.133 (5) Å | µ = 0.26 mm−1 |
β = 108.049 (5)° | T = 100 K |
V = 1284.6 (7) Å3 | Plate, colorless |
Z = 4 | 0.40 × 0.20 × 0.10 mm |
F(000) = 584 |
Bruker SMART CCD area-detector diffractometer | 2956 independent reflections |
Radiation source: fine-focus sealed tube | 2687 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.042 |
ϕ and ω scans | θmax = 27.7°, θmin = 1.5° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −19→19 |
Tmin = 0.736, Tmax = 0.974 | k = −7→7 |
10615 measured reflections | l = −20→21 |
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)] = 0.058 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.128 | All H-atom parameters refined |
S = 1.24 | w = 1/[σ2(Fo2) + (0.0403P)2 + 1.3915P] where P = (Fo2 + 2Fc2)/3 |
2956 reflections | (Δ/σ)max = 0.002 |
228 parameters | Δρmax = 0.58 e Å−3 |
0 restraints | Δρmin = −0.45 e Å−3 |
C14H14O4S | V = 1284.6 (7) Å3 |
Mr = 278.31 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 14.778 (5) Å | µ = 0.26 mm−1 |
b = 5.6665 (18) Å | T = 100 K |
c = 16.133 (5) Å | 0.40 × 0.20 × 0.10 mm |
β = 108.049 (5)° |
Bruker SMART CCD area-detector diffractometer | 2956 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2687 reflections with I > 2σ(I) |
Tmin = 0.736, Tmax = 0.974 | Rint = 0.042 |
10615 measured reflections |
R[F2 > 2σ(F2)] = 0.058 | 0 restraints |
wR(F2) = 0.128 | All H-atom parameters refined |
S = 1.24 | Δρmax = 0.58 e Å−3 |
2956 reflections | Δρmin = −0.45 e Å−3 |
228 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
S | 0.29343 (4) | 0.31557 (10) | 1.01208 (3) | 0.01666 (16) | |
O1 | 0.36007 (12) | 0.3968 (3) | 0.97108 (10) | 0.0222 (4) | |
O2 | 0.27097 (13) | 0.0713 (3) | 1.00823 (11) | 0.0255 (4) | |
O3 | 0.19711 (11) | 0.4602 (3) | 0.97292 (10) | 0.0186 (4) | |
O4 | 0.06857 (12) | 0.5138 (3) | 0.61427 (10) | 0.0204 (4) | |
C1 | 0.4361 (2) | 0.6151 (5) | 1.38654 (16) | 0.0244 (5) | |
C2 | 0.39454 (16) | 0.5464 (4) | 1.29296 (15) | 0.0169 (5) | |
C3 | 0.34358 (17) | 0.3382 (4) | 1.26940 (15) | 0.0186 (5) | |
C4 | 0.30937 (17) | 0.2696 (4) | 1.18300 (15) | 0.0170 (5) | |
C5 | 0.32683 (16) | 0.4115 (4) | 1.12017 (14) | 0.0160 (4) | |
C6 | 0.37595 (17) | 0.6218 (4) | 1.14139 (15) | 0.0186 (5) | |
C7 | 0.40901 (17) | 0.6875 (4) | 1.22803 (15) | 0.0189 (5) | |
C8 | 0.16490 (16) | 0.4770 (4) | 0.88075 (14) | 0.0158 (5) | |
C9 | 0.10953 (16) | 0.2981 (4) | 0.83259 (15) | 0.0171 (5) | |
C10 | 0.07859 (17) | 0.3181 (4) | 0.74319 (15) | 0.0170 (5) | |
C11 | 0.10301 (16) | 0.5126 (4) | 0.70274 (14) | 0.0160 (5) | |
C12 | 0.15840 (17) | 0.6912 (4) | 0.75221 (15) | 0.0181 (5) | |
C13 | 0.18938 (17) | 0.6716 (4) | 0.84253 (15) | 0.0186 (5) | |
C14 | 0.0923 (2) | 0.7116 (5) | 0.56985 (16) | 0.0257 (6) | |
H1A | 0.438 (3) | 0.775 (8) | 1.396 (3) | 0.064 (12)* | |
H1B | 0.502 (3) | 0.586 (7) | 1.404 (2) | 0.060 (11)* | |
H1C | 0.407 (3) | 0.538 (7) | 1.423 (3) | 0.065 (12)* | |
H3 | 0.332 (2) | 0.249 (5) | 1.311 (2) | 0.028 (8)* | |
H4 | 0.2766 (19) | 0.126 (5) | 1.1668 (17) | 0.020 (7)* | |
H6 | 0.3870 (18) | 0.717 (5) | 1.0984 (18) | 0.018 (7)* | |
H7 | 0.4447 (19) | 0.829 (5) | 1.2449 (18) | 0.020 (7)* | |
H9 | 0.0927 (19) | 0.165 (5) | 0.8590 (18) | 0.020 (7)* | |
H10 | 0.042 (2) | 0.207 (5) | 0.7107 (19) | 0.025 (7)* | |
H12 | 0.1737 (19) | 0.819 (5) | 0.7264 (17) | 0.017 (7)* | |
H13 | 0.2274 (19) | 0.788 (5) | 0.8764 (18) | 0.019 (7)* | |
H14A | 0.160 (2) | 0.720 (5) | 0.5829 (19) | 0.025 (7)* | |
H14B | 0.060 (2) | 0.680 (5) | 0.508 (2) | 0.028 (8)* | |
H14C | 0.065 (2) | 0.857 (5) | 0.5862 (18) | 0.025 (7)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S | 0.0244 (3) | 0.0148 (3) | 0.0106 (3) | 0.0031 (2) | 0.0051 (2) | −0.0009 (2) |
O1 | 0.0254 (9) | 0.0279 (9) | 0.0149 (8) | 0.0048 (7) | 0.0087 (7) | 0.0016 (7) |
O2 | 0.0412 (11) | 0.0161 (9) | 0.0177 (9) | 0.0022 (8) | 0.0068 (8) | −0.0025 (7) |
O3 | 0.0237 (9) | 0.0209 (8) | 0.0111 (8) | 0.0037 (7) | 0.0053 (6) | −0.0012 (6) |
O4 | 0.0282 (9) | 0.0206 (9) | 0.0113 (8) | −0.0039 (7) | 0.0048 (7) | 0.0006 (6) |
C1 | 0.0309 (14) | 0.0265 (14) | 0.0152 (12) | −0.0039 (11) | 0.0064 (10) | −0.0049 (10) |
C2 | 0.0182 (11) | 0.0172 (11) | 0.0154 (11) | 0.0028 (9) | 0.0057 (9) | −0.0019 (9) |
C3 | 0.0239 (12) | 0.0194 (12) | 0.0146 (11) | −0.0006 (9) | 0.0092 (9) | 0.0030 (9) |
C4 | 0.0225 (12) | 0.0134 (11) | 0.0160 (11) | −0.0024 (9) | 0.0075 (9) | −0.0001 (9) |
C5 | 0.0208 (11) | 0.0146 (11) | 0.0119 (10) | 0.0021 (9) | 0.0040 (8) | −0.0011 (8) |
C6 | 0.0259 (12) | 0.0147 (11) | 0.0166 (11) | 0.0011 (9) | 0.0083 (9) | 0.0042 (9) |
C7 | 0.0238 (12) | 0.0135 (11) | 0.0195 (11) | −0.0020 (9) | 0.0069 (9) | −0.0038 (9) |
C8 | 0.0200 (11) | 0.0167 (11) | 0.0100 (10) | 0.0047 (9) | 0.0036 (8) | −0.0011 (8) |
C9 | 0.0211 (11) | 0.0146 (11) | 0.0174 (11) | −0.0005 (9) | 0.0083 (9) | 0.0018 (9) |
C10 | 0.0202 (11) | 0.0129 (11) | 0.0181 (11) | −0.0001 (9) | 0.0064 (9) | −0.0038 (9) |
C11 | 0.0177 (11) | 0.0166 (11) | 0.0139 (10) | 0.0031 (9) | 0.0050 (8) | 0.0000 (9) |
C12 | 0.0217 (12) | 0.0133 (11) | 0.0191 (11) | −0.0017 (9) | 0.0059 (9) | 0.0008 (9) |
C13 | 0.0227 (12) | 0.0133 (11) | 0.0186 (11) | −0.0001 (9) | 0.0045 (9) | −0.0042 (9) |
C14 | 0.0363 (15) | 0.0242 (14) | 0.0158 (12) | −0.0039 (11) | 0.0068 (10) | 0.0043 (10) |
S—O2 | 1.4200 (19) | C5—C6 | 1.382 (3) |
S—O1 | 1.4223 (18) | C6—C7 | 1.381 (3) |
S—O3 | 1.5936 (17) | C6—H6 | 0.93 (3) |
S—C5 | 1.745 (2) | C7—H7 | 0.95 (3) |
O3—C8 | 1.417 (3) | C8—C13 | 1.366 (3) |
O4—C11 | 1.359 (3) | C8—C9 | 1.381 (3) |
O4—C14 | 1.432 (3) | C9—C10 | 1.376 (3) |
C1—C2 | 1.495 (3) | C9—H9 | 0.94 (3) |
C1—H1A | 0.92 (5) | C10—C11 | 1.385 (3) |
C1—H1B | 0.95 (4) | C10—H10 | 0.89 (3) |
C1—H1C | 0.94 (4) | C11—C12 | 1.388 (3) |
C2—C7 | 1.386 (3) | C12—C13 | 1.390 (3) |
C2—C3 | 1.388 (3) | C12—H12 | 0.90 (3) |
C3—C4 | 1.383 (3) | C13—H13 | 0.93 (3) |
C3—H3 | 0.90 (3) | C14—H14A | 0.96 (3) |
C4—C5 | 1.380 (3) | C14—H14B | 0.99 (3) |
C4—H4 | 0.94 (3) | C14—H14C | 0.98 (3) |
O2—S—O1 | 118.77 (11) | C5—C6—H6 | 120.9 (17) |
O2—S—O3 | 108.41 (11) | C6—C7—C2 | 121.4 (2) |
O1—S—O3 | 108.13 (10) | C6—C7—H7 | 120.5 (17) |
O2—S—C5 | 109.71 (11) | C2—C7—H7 | 118.1 (17) |
O1—S—C5 | 109.97 (11) | C13—C8—C9 | 122.2 (2) |
O3—S—C5 | 100.21 (10) | C13—C8—O3 | 118.6 (2) |
C8—O3—S | 114.78 (13) | C9—C8—O3 | 119.3 (2) |
C11—O4—C14 | 117.35 (18) | C10—C9—C8 | 118.4 (2) |
C2—C1—H1A | 114 (3) | C10—C9—H9 | 119.7 (17) |
C2—C1—H1B | 109 (2) | C8—C9—H9 | 121.9 (16) |
H1A—C1—H1B | 98 (3) | C9—C10—C11 | 120.6 (2) |
C2—C1—H1C | 113 (3) | C9—C10—H10 | 120.3 (19) |
H1A—C1—H1C | 110 (4) | C11—C10—H10 | 119.1 (19) |
H1B—C1—H1C | 111 (3) | O4—C11—C10 | 115.6 (2) |
C7—C2—C3 | 118.7 (2) | O4—C11—C12 | 124.3 (2) |
C7—C2—C1 | 120.1 (2) | C10—C11—C12 | 120.2 (2) |
C3—C2—C1 | 121.1 (2) | C11—C12—C13 | 119.3 (2) |
C4—C3—C2 | 120.9 (2) | C11—C12—H12 | 120.6 (17) |
C4—C3—H3 | 120 (2) | C13—C12—H12 | 120.2 (17) |
C2—C3—H3 | 119.0 (19) | C8—C13—C12 | 119.4 (2) |
C5—C4—C3 | 118.9 (2) | C8—C13—H13 | 120.3 (17) |
C5—C4—H4 | 119.9 (16) | C12—C13—H13 | 120.3 (17) |
C3—C4—H4 | 121.2 (16) | O4—C14—H14A | 109.3 (18) |
C4—C5—C6 | 121.6 (2) | O4—C14—H14B | 104.7 (17) |
C4—C5—S | 119.54 (18) | H14A—C14—H14B | 112 (2) |
C6—C5—S | 118.71 (17) | O4—C14—H14C | 109.7 (17) |
C7—C6—C5 | 118.5 (2) | H14A—C14—H14C | 112 (2) |
C7—C6—H6 | 120.7 (17) | H14B—C14—H14C | 109 (2) |
O2—S—O3—C8 | −82.6 (2) | C3—C2—C7—C6 | −1.7 (4) |
O1—S—O3—C8 | 47.4 (2) | C1—C2—C7—C6 | 176.4 (2) |
C5—S—O3—C8 | 162.5 (2) | S—O3—C8—C13 | −94.7 (2) |
C7—C2—C3—C4 | 1.3 (4) | S—O3—C8—C9 | 85.8 (2) |
C1—C2—C3—C4 | −176.7 (2) | C13—C8—C9—C10 | 0.2 (3) |
C2—C3—C4—C5 | 0.1 (4) | O3—C8—C9—C10 | 179.7 (2) |
C3—C4—C5—C6 | −1.2 (4) | C8—C9—C10—C11 | 0.4 (3) |
C3—C4—C5—S | 174.4 (2) | C14—O4—C11—C10 | −179.9 (2) |
O2—S—C5—C4 | −13.4 (2) | C14—O4—C11—C12 | 0.8 (3) |
O1—S—C5—C4 | −145.8 (2) | C9—C10—C11—O4 | 180.0 (2) |
O3—S—C5—C4 | 100.5 (2) | C9—C10—C11—C12 | −0.6 (3) |
O2—S—C5—C6 | 162.4 (2) | O4—C11—C12—C13 | 179.7 (2) |
O1—S—C5—C6 | 30.0 (2) | C10—C11—C12—C13 | 0.4 (3) |
O3—S—C5—C6 | −83.7 (2) | C9—C8—C13—C12 | −0.4 (4) |
C4—C5—C6—C7 | 0.9 (4) | O3—C8—C13—C12 | −180.0 (2) |
S—C5—C6—C7 | −174.8 (2) | C11—C12—C13—C8 | 0.1 (3) |
C5—C6—C7—C2 | 0.6 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1A···O1i | 0.92 (5) | 2.67 (4) | 3.424 (3) | 141 (3) |
C1—H1B···O1ii | 0.95 (4) | 2.96 (4) | 3.551 (3) | 122 (3) |
C1—H1C···O1iii | 0.94 (4) | 2.73 (4) | 3.534 (4) | 143 (3) |
C1—H1C···O2iii | 0.94 (4) | 2.83 (4) | 3.728 (3) | 160 (3) |
C3—H3···O1iii | 0.90 (3) | 2.61 (3) | 3.454 (3) | 155 (2) |
C6—H6···O2iv | 0.93 (3) | 2.75 (3) | 3.383 (3) | 126 (2) |
C9—H9···O4v | 0.94 (3) | 2.69 (3) | 3.414 (3) | 135 (2) |
C13—H13···O2iv | 0.93 (3) | 2.58 (3) | 3.426 (3) | 152 (2) |
C14—H14A···O2vi | 0.96 (3) | 2.84 (3) | 3.486 (4) | 125 (2) |
C14—H14A···O3vii | 0.96 (3) | 2.71 (3) | 3.131 (3) | 107 (2) |
C14—H14B···O4viii | 0.99 (3) | 2.53 (3) | 3.425 (3) | 152 (2) |
C3—H3···Cg2ix | 0.90 (3) | 3.17 | 3.742 | 124 |
C7—H7···Cg1x | 0.95 (3) | 2.88 | 3.644 | 138 |
C10—H10···Cg2xi | 0.89 (3) | 2.85 | 3.527 | 134 |
C12—H12···Cg1vii | 0.90 (3) | 3.09 | 3.781 | 135 |
Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) −x+1, y+1/2, −z+5/2; (iii) x, −y+1/2, z+1/2; (iv) x, y+1, z; (v) −x, y−1/2, −z+3/2; (vi) x, −y+1/2, z−1/2; (vii) x, −y+3/2, z−1/2; (viii) −x, −y+1, −z+1; (ix) x, −y+5/2, z+1/2; (x) −x+1, y−1/2, −z+3/2; (xi) −x, y+1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C14H14O4S |
Mr | 278.31 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 100 |
a, b, c (Å) | 14.778 (5), 5.6665 (18), 16.133 (5) |
β (°) | 108.049 (5) |
V (Å3) | 1284.6 (7) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.26 |
Crystal size (mm) | 0.40 × 0.20 × 0.10 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.736, 0.974 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10615, 2956, 2687 |
Rint | 0.042 |
(sin θ/λ)max (Å−1) | 0.653 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.058, 0.128, 1.24 |
No. of reflections | 2956 |
No. of parameters | 228 |
H-atom treatment | All H-atom parameters refined |
Δρmax, Δρmin (e Å−3) | 0.58, −0.45 |
Computer programs: SMART (Bruker, 1998), SMART, SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Sheldrick, 1998), SHELXTL.
S—O2 | 1.4200 (19) | O3—C8 | 1.417 (3) |
S—O1 | 1.4223 (18) | O4—C11 | 1.359 (3) |
S—O3 | 1.5936 (17) | O4—C14 | 1.432 (3) |
S—C5 | 1.745 (2) | C1—C2 | 1.495 (3) |
O2—S—O1 | 118.77 (11) | O1—S—C5 | 109.97 (11) |
O2—S—O3 | 108.41 (11) | O3—S—C5 | 100.21 (10) |
O1—S—O3 | 108.13 (10) | C8—O3—S | 114.78 (13) |
O2—S—C5 | 109.71 (11) | C11—O4—C14 | 117.35 (18) |
C5—S—O3—C8 | 162.5 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1A···O1i | 0.92 (5) | 2.67 (4) | 3.424 (3) | 141 (3) |
C1—H1B···O1ii | 0.95 (4) | 2.96 (4) | 3.551 (3) | 122 (3) |
C1—H1C···O1iii | 0.94 (4) | 2.73 (4) | 3.534 (4) | 143 (3) |
C1—H1C···O2iii | 0.94 (4) | 2.83 (4) | 3.728 (3) | 160 (3) |
C3—H3···O1iii | 0.90 (3) | 2.61 (3) | 3.454 (3) | 155 (2) |
C6—H6···O2iv | 0.93 (3) | 2.75 (3) | 3.383 (3) | 126 (2) |
C9—H9···O4v | 0.94 (3) | 2.69 (3) | 3.414 (3) | 135 (2) |
C13—H13···O2iv | 0.93 (3) | 2.58 (3) | 3.426 (3) | 152 (2) |
C14—H14A···O2vi | 0.96 (3) | 2.84 (3) | 3.486 (4) | 125 (2) |
C14—H14A···O3vii | 0.96 (3) | 2.71 (3) | 3.131 (3) | 107 (2) |
C14—H14B···O4viii | 0.99 (3) | 2.53 (3) | 3.425 (3) | 152 (2) |
C3—H3···Cg2ix | 0.90 (3) | 3.17 | 3.742 | 124 |
C7—H7···Cg1x | 0.95 (3) | 2.88 | 3.644 | 138 |
C10—H10···Cg2xi | 0.89 (3) | 2.85 | 3.527 | 134 |
C12—H12···Cg1vii | 0.90 (3) | 3.09 | 3.781 | 135 |
Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) −x+1, y+1/2, −z+5/2; (iii) x, −y+1/2, z+1/2; (iv) x, y+1, z; (v) −x, y−1/2, −z+3/2; (vi) x, −y+1/2, z−1/2; (vii) x, −y+3/2, z−1/2; (viii) −x, −y+1, −z+1; (ix) x, −y+5/2, z+1/2; (x) −x+1, y−1/2, −z+3/2; (xi) −x, y+1/2, −z+1/2. |
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p-Toluenesulfonates are used in monitoring the merging of lipids (Yachi et al., 1989), studying membrane fusion during acrosome reaction (Spungin et al., 1992), development of immunoaffinity chromatography for the purification of human coagulation factor (Tharakan et al., 1992), chemical studies on viruses (Alford et al., 1991), development of technology for linking photosensitizer to model monoclonal antibody (Jiang et al., 1990) and chemical modification of sigma sub units of the E. coli RNA polymerase (Narayanan & Krakow, 1983). An X-ray study of the title compound, (I), was undertaken in order to determine its crystal and molecular structure owing to the biological importance of its analogues.
A search of Version 5.23 (July 2002 updates) of the Cambridge Structural Database (Allen, 2002) revealed 16 structures (with the following refcodes: KAWDAN, FIXCAQ, NEDXUP, NEDYAW, NEDYIE, NUNCII, RASSOT, RELVUZ, SIMVUF, TCPTOS, TEBFOV, TMPDTS, TSMIPH, WOHCUR, ZZZBDA10 and MIWHIJ) that are closely related to the title compound (I). The S—C, S—O and S═O bond lengths (Table 1) are comparable to those found in these structures. The dihedral angle between the mean planes of the 4-tolyl and the 4-methoxyphenyl rings is 7.2 (1)°. This shows their near coplanar orientation similar to that found between the mean planes of the 4-tolyl and 2,4-dinitrophenyl rings in 2,4-dinitrophenyl 4-toluenesulfonate (Vembu et al., 2003a) and in contrast to the non-coplanar orientation of 4-tolyl and 2-chlorophenyl rings in 2-chlorophenyl 4-toluenesulfonate (Vembu et al., 2003b) and the non-coplanar orientation of the 4-tolyl and quinoline rings in 8-tosyloxyquinoline (Vembu et al., 2003c).
The crystal structure of (I) is stabilized by weak C—H···O interactions (Table 2). The range of the H···O distances agree with those found for weak C—H···O bonds (Desiraju & Steiner, 1999). The C3—H3···O1iii and C1—H1C···O1iii interactions constitute a pair of bifurcated acceptor bonds involving H atoms of the neighbouring 4-tolyl moiety (see Table 2 for symmetry code). They generate a ring of graph set (Etter, 1990; Bernstein et al., 1995) motif R12(6). The C1—H1C···O1iii and C1—H1C···O2iii interactions form a pair of bifurcated donor bonds involving the sulfonyl O atoms. They generate a ring of graph set motif R21(4). The H1C···O1iii and H1C···O2iii distances differ by 0.10 Å. The resulting configuration is best regarded as a three center symmetrical hydrogen-bonded chelate (Desiraju, 1989) and is also observed in 2-chlorophenyl 4-toluenesulfonate (Vembu et al., 2003b), 8-tosyloxyquinoline (Vembu et al., 2003c) and 4-dimethylaminopyridinium picrate (Vembu et al., 2003 d). The inter-fusion of R12(6) and R21(4) motifs generate a ring of graph set motif R22(8). The C6—H6···O2iv and C13—H13···O2iv interactions constitute a pair of bifurcated acceptor bonds involving the H atoms of the neighbouring 4-tolyl and 4-methoxyphenyl moieties (see Table 2 for symmetry code). They generate a ring of graph-set motif R12(9) (Fig. 2).
The supramolecular aggregation is completed by the presence of four C—H···π interactions which pack the molecules in a slip stack along the b axis (Fig. 3). The geometry of the C—H···π interactions obtained from PLATON (Spek, 1998) is given in Table 2, where Cg1 and Cg2 are the centroids of the 4-tolyl and 4-methoxyphenyl rings, respectively.