Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803013291/ob6259sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803013291/ob6259Isup2.hkl |
CCDC reference: 217604
4-Toluenesulfonyl chloride (4.9 mmol) dissolved in acetone (15 ml) was added to a mixture of phloroglucinol (4.9 mmol) and triethylamine (4.9 mmol) in 30 ml acetone. The solution was kept overnight and evaporated. The residue was washed several times with water and the crude title compound (0.8 mmol, yield: 50%) was recrystallized from a 1:1 mixture of ethanol and acetone.
All the H atoms were located from the difference Fourier maps and refined isotropically. The C—H bond lengths are in the range 0.84 (4)–0.99 (4) Å, the H—C—H angles for the methyl group are in the range 103 (3)–112 (3)° and the C—C—H angles for the aromatic rings are in the range 118.4 (2)–122.2 (2)°.
Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
C27H24O9S3 | Dx = 1.454 Mg m−3 |
Mr = 588.64 | Melting point = 357–359 K |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 9.8953 (14) Å | Cell parameters from 8345 reflections |
b = 11.6682 (17) Å | θ = 2.5–28.3° |
c = 23.626 (3) Å | µ = 0.33 mm−1 |
β = 99.719 (3)° | T = 100 K |
V = 2688.8 (7) Å3 | Block, colorless |
Z = 4 | 0.30 × 0.20 × 0.10 mm |
F(000) = 1224 |
Bruker CCD area-detector diffractometer | 6509 independent reflections |
Radiation source: fine-focus sealed tube | 5840 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.040 |
ϕ and ω scans | θmax = 28.3°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −12→12 |
Tmin = 0.908, Tmax = 0.968 | k = −15→15 |
33621 measured reflections | l = −31→31 |
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)] = 0.054 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.116 | All H-atom parameters refined |
S = 1.18 | w = 1/[σ2(Fo2) + (0.0392P)2 + 2.7273P] where P = (Fo2 + 2Fc2)/3 |
6509 reflections | (Δ/σ)max < 0.001 |
448 parameters | Δρmax = 0.55 e Å−3 |
0 restraints | Δρmin = −0.37 e Å−3 |
C27H24O9S3 | V = 2688.8 (7) Å3 |
Mr = 588.64 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 9.8953 (14) Å | µ = 0.33 mm−1 |
b = 11.6682 (17) Å | T = 100 K |
c = 23.626 (3) Å | 0.30 × 0.20 × 0.10 mm |
β = 99.719 (3)° |
Bruker CCD area-detector diffractometer | 6509 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 5840 reflections with I > 2σ(I) |
Tmin = 0.908, Tmax = 0.968 | Rint = 0.040 |
33621 measured reflections |
R[F2 > 2σ(F2)] = 0.054 | 0 restraints |
wR(F2) = 0.116 | All H-atom parameters refined |
S = 1.18 | Δρmax = 0.55 e Å−3 |
6509 reflections | Δρmin = −0.37 e Å−3 |
448 parameters |
Experimental. The Tmin and Tmax values obtained from the SIZE instruction are listed above. The absorption correction was applied using SADABS and it gives 0.921655 ratio of min/max transmission" |
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 | ||
S1 | 1.12899 (6) | 0.68996 (5) | 0.51347 (2) | 0.02276 (13) | |
S2 | 0.58000 (6) | 0.73964 (5) | 0.37889 (3) | 0.02139 (13) | |
S3 | 1.06649 (5) | 0.91812 (5) | 0.26207 (2) | 0.01924 (13) | |
O1 | 1.11165 (16) | 0.60656 (13) | 0.45856 (6) | 0.0205 (3) | |
O2 | 0.99741 (18) | 0.71509 (16) | 0.52669 (7) | 0.0314 (4) | |
O3 | 1.22792 (19) | 0.63251 (16) | 0.55430 (7) | 0.0345 (4) | |
O4 | 0.66775 (15) | 0.66383 (13) | 0.34100 (7) | 0.0221 (3) | |
O5 | 0.44327 (16) | 0.70332 (15) | 0.35868 (8) | 0.0308 (4) | |
O6 | 0.63878 (17) | 0.72817 (15) | 0.43814 (7) | 0.0276 (4) | |
O7 | 1.08016 (15) | 0.78202 (13) | 0.27481 (6) | 0.0206 (3) | |
O8 | 1.04003 (17) | 0.97429 (14) | 0.31243 (7) | 0.0270 (4) | |
O9 | 1.18614 (16) | 0.94287 (15) | 0.23841 (7) | 0.0269 (4) | |
C1 | 1.0288 (2) | 0.64672 (18) | 0.40797 (9) | 0.0182 (4) | |
C2 | 0.8878 (2) | 0.63370 (18) | 0.40147 (9) | 0.0182 (4) | |
C3 | 0.8120 (2) | 0.67488 (18) | 0.35121 (9) | 0.0182 (4) | |
C4 | 0.8709 (2) | 0.72427 (19) | 0.30794 (9) | 0.0194 (4) | |
C5 | 1.0122 (2) | 0.73467 (18) | 0.31713 (9) | 0.0183 (4) | |
C6 | 1.0940 (2) | 0.69661 (18) | 0.36672 (9) | 0.0175 (4) | |
C7 | 1.1951 (2) | 0.81498 (19) | 0.48827 (9) | 0.0195 (4) | |
C8 | 1.3326 (2) | 0.8201 (2) | 0.48292 (10) | 0.0213 (4) | |
C9 | 1.3805 (2) | 0.9182 (2) | 0.46004 (10) | 0.0232 (5) | |
C10 | 1.2946 (2) | 1.01024 (19) | 0.44236 (9) | 0.0218 (5) | |
C11 | 1.1571 (2) | 1.0022 (2) | 0.44825 (10) | 0.0234 (5) | |
C12 | 1.1068 (2) | 0.9051 (2) | 0.47064 (9) | 0.0220 (5) | |
C13 | 1.3469 (3) | 1.1169 (2) | 0.41781 (13) | 0.0322 (6) | |
C14 | 0.6011 (2) | 0.88092 (18) | 0.35716 (9) | 0.0185 (4) | |
C15 | 0.7125 (2) | 0.9447 (2) | 0.38417 (9) | 0.0210 (4) | |
C16 | 0.7237 (2) | 1.0577 (2) | 0.36747 (10) | 0.0239 (5) | |
C17 | 0.6261 (3) | 1.1077 (2) | 0.32550 (10) | 0.0240 (5) | |
C18 | 0.5159 (3) | 1.0414 (2) | 0.29968 (10) | 0.0245 (5) | |
C19 | 0.5023 (2) | 0.9286 (2) | 0.31497 (10) | 0.0223 (5) | |
C20 | 0.6394 (4) | 1.2302 (2) | 0.30772 (14) | 0.0379 (7) | |
C21 | 0.9218 (2) | 0.92560 (18) | 0.20803 (9) | 0.0172 (4) | |
C22 | 0.7983 (2) | 0.96398 (19) | 0.22156 (9) | 0.0205 (4) | |
C23 | 0.6840 (2) | 0.96663 (19) | 0.17877 (10) | 0.0213 (4) | |
C24 | 0.6917 (2) | 0.93241 (18) | 0.12295 (9) | 0.0206 (4) | |
C25 | 0.8170 (2) | 0.89394 (19) | 0.11074 (9) | 0.0201 (4) | |
C26 | 0.9326 (2) | 0.89023 (18) | 0.15278 (9) | 0.0183 (4) | |
C27 | 0.5690 (3) | 0.9395 (3) | 0.07599 (12) | 0.0326 (6) | |
H2 | 0.847 (3) | 0.602 (2) | 0.4284 (11) | 0.020 (6)* | |
H4 | 0.816 (3) | 0.749 (2) | 0.2748 (11) | 0.022 (6)* | |
H6 | 1.188 (3) | 0.703 (2) | 0.3725 (11) | 0.021 (6)* | |
H8 | 1.392 (3) | 0.759 (2) | 0.4960 (11) | 0.026 (7)* | |
H9 | 1.474 (3) | 0.924 (2) | 0.4565 (11) | 0.024 (7)* | |
H11 | 1.100 (3) | 1.062 (2) | 0.4357 (11) | 0.023 (7)* | |
H12 | 1.014 (3) | 0.901 (2) | 0.4748 (11) | 0.028 (7)* | |
H13A | 1.293 (3) | 1.130 (3) | 0.3811 (15) | 0.049 (9)* | |
H13B | 1.442 (3) | 1.110 (3) | 0.4124 (13) | 0.040 (8)* | |
H13C | 1.341 (3) | 1.178 (3) | 0.4433 (13) | 0.038 (8)* | |
H15 | 0.780 (3) | 0.911 (2) | 0.4135 (11) | 0.024 (7)* | |
H16 | 0.799 (3) | 1.101 (2) | 0.3854 (12) | 0.030 (7)* | |
H18 | 0.449 (3) | 1.071 (2) | 0.2721 (12) | 0.029 (7)* | |
H19 | 0.429 (3) | 0.885 (2) | 0.2991 (12) | 0.029 (7)* | |
H20A | 0.683 (4) | 1.233 (3) | 0.2771 (17) | 0.061 (11)* | |
H20B | 0.556 (4) | 1.266 (4) | 0.2964 (17) | 0.071 (13)* | |
H20C | 0.690 (4) | 1.275 (3) | 0.3374 (16) | 0.056 (10)* | |
H22 | 0.791 (3) | 0.985 (2) | 0.2576 (11) | 0.021 (6)* | |
H23 | 0.597 (3) | 0.993 (2) | 0.1882 (11) | 0.025 (7)* | |
H25 | 0.824 (3) | 0.872 (2) | 0.0737 (11) | 0.022 (6)* | |
H26 | 1.017 (3) | 0.865 (2) | 0.1447 (11) | 0.021 (6)* | |
H27A | 0.583 (4) | 0.901 (3) | 0.0399 (16) | 0.059 (10)* | |
H27B | 0.499 (4) | 0.912 (4) | 0.0862 (17) | 0.070 (13)* | |
H27C | 0.554 (4) | 1.020 (3) | 0.0646 (15) | 0.059 (10)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0240 (3) | 0.0286 (3) | 0.0158 (2) | −0.0043 (2) | 0.0038 (2) | 0.0036 (2) |
S2 | 0.0159 (3) | 0.0202 (3) | 0.0289 (3) | −0.0009 (2) | 0.0061 (2) | 0.0012 (2) |
S3 | 0.0182 (3) | 0.0209 (3) | 0.0175 (2) | 0.0005 (2) | 0.00002 (19) | 0.0027 (2) |
O1 | 0.0213 (8) | 0.0200 (7) | 0.0195 (7) | 0.0014 (6) | 0.0014 (6) | 0.0042 (6) |
O2 | 0.0318 (10) | 0.0396 (10) | 0.0260 (9) | −0.0087 (8) | 0.0139 (7) | −0.0022 (8) |
O3 | 0.0388 (10) | 0.0378 (10) | 0.0233 (9) | −0.0060 (8) | −0.0048 (8) | 0.0100 (8) |
O4 | 0.0140 (7) | 0.0226 (8) | 0.0291 (8) | −0.0013 (6) | 0.0023 (6) | −0.0038 (7) |
O5 | 0.0169 (8) | 0.0248 (9) | 0.0513 (11) | −0.0034 (7) | 0.0075 (8) | 0.0002 (8) |
O6 | 0.0274 (9) | 0.0297 (9) | 0.0275 (9) | 0.0061 (7) | 0.0097 (7) | 0.0064 (7) |
O7 | 0.0207 (8) | 0.0218 (8) | 0.0201 (7) | 0.0041 (6) | 0.0058 (6) | 0.0051 (6) |
O8 | 0.0312 (9) | 0.0270 (9) | 0.0206 (8) | 0.0009 (7) | −0.0021 (7) | −0.0020 (7) |
O9 | 0.0195 (8) | 0.0312 (9) | 0.0291 (9) | −0.0028 (7) | 0.0014 (7) | 0.0074 (7) |
C1 | 0.0211 (11) | 0.0160 (10) | 0.0164 (9) | 0.0030 (8) | 0.0001 (8) | −0.0002 (8) |
C2 | 0.0207 (11) | 0.0134 (9) | 0.0217 (10) | −0.0014 (8) | 0.0067 (9) | −0.0005 (8) |
C3 | 0.0145 (10) | 0.0159 (10) | 0.0239 (11) | 0.0004 (8) | 0.0021 (8) | −0.0046 (8) |
C4 | 0.0192 (10) | 0.0192 (10) | 0.0189 (10) | 0.0040 (8) | 0.0007 (8) | −0.0006 (8) |
C5 | 0.0197 (10) | 0.0155 (10) | 0.0204 (10) | 0.0017 (8) | 0.0056 (8) | −0.0007 (8) |
C6 | 0.0147 (10) | 0.0176 (10) | 0.0204 (10) | 0.0024 (8) | 0.0035 (8) | −0.0026 (8) |
C7 | 0.0221 (11) | 0.0219 (11) | 0.0143 (9) | −0.0007 (8) | 0.0024 (8) | −0.0004 (8) |
C8 | 0.0184 (11) | 0.0217 (11) | 0.0238 (11) | 0.0020 (9) | 0.0035 (9) | −0.0016 (9) |
C9 | 0.0200 (11) | 0.0231 (11) | 0.0278 (11) | −0.0009 (9) | 0.0078 (9) | −0.0044 (9) |
C10 | 0.0262 (12) | 0.0214 (11) | 0.0186 (10) | 0.0004 (9) | 0.0061 (9) | −0.0037 (9) |
C11 | 0.0248 (12) | 0.0254 (11) | 0.0200 (10) | 0.0088 (9) | 0.0039 (9) | −0.0008 (9) |
C12 | 0.0172 (11) | 0.0296 (12) | 0.0198 (10) | 0.0020 (9) | 0.0046 (8) | −0.0030 (9) |
C13 | 0.0398 (16) | 0.0231 (12) | 0.0362 (14) | −0.0008 (11) | 0.0138 (12) | 0.0014 (11) |
C14 | 0.0170 (10) | 0.0191 (10) | 0.0203 (10) | −0.0003 (8) | 0.0056 (8) | −0.0011 (8) |
C15 | 0.0168 (10) | 0.0268 (11) | 0.0191 (10) | −0.0011 (9) | 0.0018 (8) | −0.0008 (9) |
C16 | 0.0243 (12) | 0.0259 (12) | 0.0228 (11) | −0.0075 (9) | 0.0074 (9) | −0.0055 (9) |
C17 | 0.0317 (13) | 0.0225 (11) | 0.0206 (10) | 0.0008 (9) | 0.0124 (9) | −0.0008 (9) |
C18 | 0.0264 (12) | 0.0289 (12) | 0.0181 (10) | 0.0067 (10) | 0.0035 (9) | 0.0004 (9) |
C19 | 0.0168 (11) | 0.0274 (12) | 0.0219 (10) | 0.0006 (9) | 0.0010 (8) | −0.0050 (9) |
C20 | 0.0527 (19) | 0.0256 (13) | 0.0380 (16) | −0.0035 (13) | 0.0155 (14) | 0.0049 (12) |
C21 | 0.0168 (10) | 0.0186 (10) | 0.0154 (9) | 0.0006 (8) | −0.0001 (8) | 0.0040 (8) |
C22 | 0.0231 (11) | 0.0232 (11) | 0.0158 (10) | 0.0059 (9) | 0.0053 (8) | 0.0024 (8) |
C23 | 0.0179 (11) | 0.0238 (11) | 0.0221 (11) | 0.0050 (9) | 0.0036 (9) | 0.0016 (9) |
C24 | 0.0216 (11) | 0.0166 (10) | 0.0221 (10) | 0.0003 (8) | −0.0004 (9) | 0.0015 (8) |
C25 | 0.0262 (11) | 0.0182 (10) | 0.0158 (10) | −0.0004 (8) | 0.0031 (8) | −0.0024 (8) |
C26 | 0.0187 (10) | 0.0188 (10) | 0.0184 (10) | 0.0031 (8) | 0.0063 (8) | 0.0016 (8) |
C27 | 0.0298 (14) | 0.0357 (15) | 0.0285 (13) | 0.0063 (11) | −0.0062 (11) | −0.0061 (11) |
S1—O2 | 1.4199 (19) | C11—H11 | 0.92 (3) |
S1—O3 | 1.4211 (18) | C12—H12 | 0.95 (3) |
S1—O1 | 1.6077 (16) | C13—H13A | 0.95 (3) |
S1—C7 | 1.744 (2) | C13—H13B | 0.97 (3) |
S2—O5 | 1.4212 (17) | C13—H13C | 0.94 (3) |
S2—O6 | 1.4286 (18) | C14—C19 | 1.389 (3) |
S2—O4 | 1.6126 (16) | C14—C15 | 1.392 (3) |
S2—C14 | 1.750 (2) | C15—C16 | 1.386 (3) |
S3—O8 | 1.4209 (17) | C15—H15 | 0.96 (3) |
S3—O9 | 1.4216 (17) | C16—C17 | 1.390 (3) |
S3—O7 | 1.6177 (16) | C16—H16 | 0.94 (3) |
S3—C21 | 1.752 (2) | C17—C18 | 1.391 (3) |
O1—C1 | 1.410 (2) | C17—C20 | 1.502 (3) |
O4—C3 | 1.412 (3) | C18—C19 | 1.378 (3) |
O7—C5 | 1.408 (3) | C18—H18 | 0.91 (3) |
C1—C6 | 1.385 (3) | C19—H19 | 0.91 (3) |
C1—C2 | 1.386 (3) | C20—H20A | 0.90 (4) |
C2—C3 | 1.379 (3) | C20—H20B | 0.92 (4) |
C2—H2 | 0.89 (3) | C20—H20C | 0.95 (4) |
C3—C4 | 1.385 (3) | C21—C22 | 1.388 (3) |
C4—C5 | 1.384 (3) | C21—C26 | 1.390 (3) |
C4—H4 | 0.92 (3) | C22—C23 | 1.384 (3) |
C5—C6 | 1.380 (3) | C22—H22 | 0.90 (3) |
C6—H6 | 0.92 (3) | C23—C24 | 1.392 (3) |
C7—C12 | 1.385 (3) | C23—H23 | 0.97 (3) |
C7—C8 | 1.388 (3) | C24—C25 | 1.394 (3) |
C8—C9 | 1.384 (3) | C24—C27 | 1.502 (3) |
C8—H8 | 0.94 (3) | C25—C26 | 1.384 (3) |
C9—C10 | 1.389 (3) | C25—H25 | 0.92 (3) |
C9—H9 | 0.94 (3) | C26—H26 | 0.94 (3) |
C10—C11 | 1.394 (3) | C27—H27A | 0.99 (4) |
C10—C13 | 1.502 (3) | C27—H27B | 0.84 (4) |
C11—C12 | 1.378 (3) | C27—H27C | 0.98 (4) |
O2—S1—O3 | 120.02 (11) | C7—C12—H12 | 120.3 (17) |
O2—S1—O1 | 109.00 (10) | C10—C13—H13A | 108 (2) |
O3—S1—O1 | 103.28 (10) | C10—C13—H13B | 112.7 (18) |
O2—S1—C7 | 108.25 (11) | H13A—C13—H13B | 107 (3) |
O3—S1—C7 | 111.79 (11) | C10—C13—H13C | 108.5 (19) |
O1—S1—C7 | 103.05 (9) | H13A—C13—H13C | 112 (3) |
O5—S2—O6 | 120.55 (11) | H13B—C13—H13C | 108 (3) |
O5—S2—O4 | 102.78 (10) | C19—C14—C15 | 121.4 (2) |
O6—S2—O4 | 108.92 (9) | C19—C14—S2 | 118.90 (17) |
O5—S2—C14 | 109.67 (11) | C15—C14—S2 | 119.59 (17) |
O6—S2—C14 | 109.07 (11) | C16—C15—C14 | 118.2 (2) |
O4—S2—C14 | 104.58 (9) | C16—C15—H15 | 120.9 (16) |
O8—S3—O9 | 121.26 (11) | C14—C15—H15 | 120.9 (16) |
O8—S3—O7 | 108.56 (9) | C15—C16—C17 | 121.5 (2) |
O9—S3—O7 | 102.92 (9) | C15—C16—H16 | 118.4 (17) |
O8—S3—C21 | 110.11 (10) | C17—C16—H16 | 120.0 (17) |
O9—S3—C21 | 109.62 (10) | C16—C17—C18 | 118.6 (2) |
O7—S3—C21 | 102.52 (9) | C16—C17—C20 | 121.1 (2) |
C1—O1—S1 | 116.77 (13) | C18—C17—C20 | 120.4 (2) |
C3—O4—S2 | 118.57 (13) | C19—C18—C17 | 121.3 (2) |
C5—O7—S3 | 118.84 (13) | C19—C18—H18 | 117.1 (18) |
C6—C1—C2 | 123.2 (2) | C17—C18—H18 | 121.5 (18) |
C6—C1—O1 | 117.59 (19) | C18—C19—C14 | 118.9 (2) |
C2—C1—O1 | 119.19 (19) | C18—C19—H19 | 122.2 (18) |
C3—C2—C1 | 116.6 (2) | C14—C19—H19 | 118.9 (18) |
C3—C2—H2 | 121.1 (16) | C17—C20—H20A | 110 (2) |
C1—C2—H2 | 122.2 (16) | C17—C20—H20B | 114 (3) |
C2—C3—C4 | 123.0 (2) | H20A—C20—H20B | 106 (3) |
C2—C3—O4 | 120.16 (19) | C17—C20—H20C | 112 (2) |
C4—C3—O4 | 116.80 (19) | H20A—C20—H20C | 108 (3) |
C5—C4—C3 | 117.4 (2) | H20B—C20—H20C | 107 (3) |
C5—C4—H4 | 122.6 (16) | C22—C21—C26 | 121.5 (2) |
C3—C4—H4 | 119.9 (16) | C22—C21—S3 | 119.40 (16) |
C6—C5—C4 | 122.5 (2) | C26—C21—S3 | 119.10 (17) |
C6—C5—O7 | 116.58 (19) | C23—C22—C21 | 118.8 (2) |
C4—C5—O7 | 120.92 (19) | C23—C22—H22 | 119.7 (16) |
C5—C6—C1 | 117.2 (2) | C21—C22—H22 | 121.5 (16) |
C5—C6—H6 | 122.1 (16) | C22—C23—C24 | 121.1 (2) |
C1—C6—H6 | 120.7 (16) | C22—C23—H23 | 119.1 (15) |
C12—C7—C8 | 121.2 (2) | C24—C23—H23 | 119.8 (15) |
C12—C7—S1 | 118.90 (18) | C23—C24—C25 | 118.7 (2) |
C8—C7—S1 | 119.79 (17) | C23—C24—C27 | 121.2 (2) |
C9—C8—C7 | 118.5 (2) | C25—C24—C27 | 120.1 (2) |
C9—C8—H8 | 121.2 (17) | C26—C25—C24 | 121.2 (2) |
C7—C8—H8 | 120.3 (17) | C26—C25—H25 | 119.2 (16) |
C8—C9—C10 | 121.6 (2) | C24—C25—H25 | 119.5 (16) |
C8—C9—H9 | 120.0 (16) | C25—C26—C21 | 118.6 (2) |
C10—C9—H9 | 118.4 (16) | C25—C26—H26 | 121.6 (15) |
C9—C10—C11 | 118.4 (2) | C21—C26—H26 | 119.8 (15) |
C9—C10—C13 | 121.5 (2) | C24—C27—H27A | 113 (2) |
C11—C10—C13 | 120.0 (2) | C24—C27—H27B | 112 (3) |
C12—C11—C10 | 121.0 (2) | H27A—C27—H27B | 109 (3) |
C12—C11—H11 | 120.5 (17) | C24—C27—H27C | 109 (2) |
C10—C11—H11 | 118.5 (17) | H27A—C27—H27C | 103 (3) |
C11—C12—C7 | 119.3 (2) | H27B—C27—H27C | 110 (3) |
C11—C12—H12 | 120.4 (17) | ||
O2—S1—O1—C1 | 57.61 (17) | C9—C10—C11—C12 | −0.5 (3) |
O3—S1—O1—C1 | −173.71 (15) | C13—C10—C11—C12 | 180.0 (2) |
C7—S1—O1—C1 | −57.22 (17) | C10—C11—C12—C7 | 1.0 (3) |
O5—S2—O4—C3 | −177.82 (16) | C8—C7—C12—C11 | −1.1 (3) |
O6—S2—O4—C3 | −48.87 (18) | S1—C7—C12—C11 | −177.10 (17) |
C14—S2—O4—C3 | 67.62 (17) | O5—S2—C14—C19 | −14.2 (2) |
O8—S3—O7—C5 | 26.29 (18) | O6—S2—C14—C19 | −148.24 (17) |
O9—S3—O7—C5 | 155.98 (15) | O4—S2—C14—C19 | 95.38 (18) |
C21—S3—O7—C5 | −90.20 (16) | O5—S2—C14—C15 | 162.78 (18) |
S1—O1—C1—C6 | 97.7 (2) | O6—S2—C14—C15 | 28.8 (2) |
S1—O1—C1—C2 | −83.0 (2) | O4—S2—C14—C15 | −87.60 (19) |
C6—C1—C2—C3 | −0.9 (3) | C19—C14—C15—C16 | −0.7 (3) |
O1—C1—C2—C3 | 179.82 (18) | S2—C14—C15—C16 | −177.64 (17) |
C1—C2—C3—C4 | 1.8 (3) | C14—C15—C16—C17 | 0.9 (3) |
C1—C2—C3—O4 | 179.31 (18) | C15—C16—C17—C18 | −0.6 (3) |
S2—O4—C3—C2 | 69.9 (2) | C15—C16—C17—C20 | −180.0 (2) |
S2—O4—C3—C4 | −112.43 (19) | C16—C17—C18—C19 | 0.1 (3) |
C2—C3—C4—C5 | −1.8 (3) | C20—C17—C18—C19 | 179.4 (2) |
O4—C3—C4—C5 | −179.40 (18) | C17—C18—C19—C14 | 0.1 (3) |
C3—C4—C5—C6 | 0.9 (3) | C15—C14—C19—C18 | 0.2 (3) |
C3—C4—C5—O7 | 178.83 (18) | S2—C14—C19—C18 | 177.17 (17) |
S3—O7—C5—C6 | −110.68 (18) | O8—S3—C21—C22 | −10.6 (2) |
S3—O7—C5—C4 | 71.3 (2) | O9—S3—C21—C22 | −146.45 (18) |
C4—C5—C6—C1 | −0.1 (3) | O7—S3—C21—C22 | 104.75 (18) |
O7—C5—C6—C1 | −178.11 (18) | O8—S3—C21—C26 | 170.92 (17) |
C2—C1—C6—C5 | 0.1 (3) | O9—S3—C21—C26 | 35.1 (2) |
O1—C1—C6—C5 | 179.39 (18) | O7—S3—C21—C26 | −73.71 (18) |
O2—S1—C7—C12 | −16.5 (2) | C26—C21—C22—C23 | 0.1 (3) |
O3—S1—C7—C12 | −150.86 (18) | S3—C21—C22—C23 | −178.34 (17) |
O1—S1—C7—C12 | 98.86 (18) | C21—C22—C23—C24 | −0.4 (3) |
O2—S1—C7—C8 | 167.41 (17) | C22—C23—C24—C25 | 0.7 (3) |
O3—S1—C7—C8 | 33.1 (2) | C22—C23—C24—C27 | −177.7 (2) |
O1—S1—C7—C8 | −77.22 (19) | C23—C24—C25—C26 | −0.5 (3) |
C12—C7—C8—C9 | 0.7 (3) | C27—C24—C25—C26 | 177.8 (2) |
S1—C7—C8—C9 | 176.73 (17) | C24—C25—C26—C21 | 0.1 (3) |
C7—C8—C9—C10 | −0.3 (3) | C22—C21—C26—C25 | 0.1 (3) |
C8—C9—C10—C11 | 0.2 (3) | S3—C21—C26—C25 | 178.49 (16) |
C8—C9—C10—C13 | 179.7 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···O2 | 0.89 (3) | 2.86 (2) | 3.122 (3) | 98.9 (18) |
C2—H2···O6 | 0.89 (3) | 2.58 (3) | 2.959 (3) | 106.9 (19) |
C8—H8···O3 | 0.94 (3) | 2.73 (3) | 3.049 (3) | 100.7 (18) |
C12—H12···O2 | 0.95 (3) | 2.51 (3) | 2.885 (3) | 104.0 (19) |
C15—H15···O6 | 0.96 (3) | 2.67 (3) | 2.976 (3) | 99.1 (17) |
C19—H19···O5 | 0.91 (3) | 2.53 (3) | 2.919 (3) | 106 (2) |
C22—H22···O8 | 0.90 (3) | 2.59 (3) | 2.934 (3) | 103.6 (18) |
C26—H26···O9 | 0.94 (3) | 2.70 (2) | 3.008 (3) | 100.4 (17) |
C2—H2···O3i | 0.89 (3) | 2.88 (3) | 3.529 (3) | 131 (2) |
C6—H6···O5ii | 0.92 (3) | 2.60 (3) | 3.494 (3) | 164 (2) |
C8—H8···O6ii | 0.94 (3) | 3.02 (3) | 3.540 (3) | 116.8 (19) |
C9—H9···O6ii | 0.94 (3) | 2.89 (3) | 3.488 (3) | 122.9 (19) |
C11—H11···O2iii | 0.92 (3) | 2.96 (3) | 3.725 (3) | 142 (2) |
C13—H13C···O6iii | 0.94 (3) | 2.98 (3) | 3.835 (3) | 151 (2) |
C18—H18···O4iv | 0.91 (3) | 2.94 (3) | 3.788 (3) | 156 (2) |
C18—H18···O9v | 0.91 (3) | 2.99 (3) | 3.531 (3) | 120 (2) |
C19—H19···O9v | 0.91 (3) | 2.67 (3) | 3.343 (3) | 131 (2) |
C20—H20A···O7vi | 0.90 (4) | 2.88 (4) | 3.701 (4) | 152 (3) |
C20—H20A···O9vi | 0.90 (4) | 2.82 (4) | 3.311 (3) | 116 (3) |
C20—H20C···O3iii | 0.95 (4) | 2.77 (4) | 3.670 (4) | 159 (3) |
C20—H20A···O9vi | 0.90 (4) | 2.82 (4) | 3.311 (3) | 116 (3) |
C23—H23···O5iv | 0.97 (3) | 2.70 (3) | 3.102 (3) | 105.4 (18) |
C25—H25···O1vi | 0.92 (3) | 2.94 (3) | 3.118 (3) | 92.5 (17) |
C25—H25···O2vii | 0.92 (3) | 2.42 (3) | 3.154 (3) | 136 (2) |
C26—H26···O2vii | 0.94 (3) | 2.92 (3) | 3.382 (3) | 112.1 (18) |
C27—H27A···O6vii | 0.99 (4) | 2.97 (4) | 3.958 (3) | 175 (3) |
C27—H27B···O3viii | 0.84 (4) | 2.71 (4) | 3.431 (4) | 145 (3) |
C27—H27C···O5iv | 0.98 (4) | 2.80 (4) | 3.455 (3) | 125 (3) |
C6—H6···Cg2 | 0.92 (3) | 3.26 | 3.576 | 102.5 |
C22—H22···Cg3 | 0.90 (3) | 2.86 | 3.638 | 145.2 |
C13—H13B···Cg3v | 0.97 (3) | 2.98 | 3.728 | 141.6 |
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) x+1, y, z; (iii) −x+2, −y+2, −z+1; (iv) −x+1, y+1/2, −z+1/2; (v) x−1, y, z; (vi) −x+2, y+1/2, −z+1/2; (vii) x, −y+3/2, z−1/2; (viii) x−1, −y+3/2, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C27H24O9S3 |
Mr | 588.64 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 100 |
a, b, c (Å) | 9.8953 (14), 11.6682 (17), 23.626 (3) |
β (°) | 99.719 (3) |
V (Å3) | 2688.8 (7) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.33 |
Crystal size (mm) | 0.30 × 0.20 × 0.10 |
Data collection | |
Diffractometer | Bruker CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.908, 0.968 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 33621, 6509, 5840 |
Rint | 0.040 |
(sin θ/λ)max (Å−1) | 0.667 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.054, 0.116, 1.18 |
No. of reflections | 6509 |
No. of parameters | 448 |
H-atom treatment | All H-atom parameters refined |
Δρmax, Δρmin (e Å−3) | 0.55, −0.37 |
Computer programs: SMART (Bruker, 1998), SMART, SAINT (Bruker, 1998), SHELXTL (Sheldrick, 1998), SHELXTL.
S1—O2 | 1.4199 (19) | S3—O8 | 1.4209 (17) |
S1—O3 | 1.4211 (18) | S3—O9 | 1.4216 (17) |
S1—O1 | 1.6077 (16) | S3—O7 | 1.6177 (16) |
S1—C7 | 1.744 (2) | S3—C21 | 1.752 (2) |
S2—O5 | 1.4212 (17) | O1—C1 | 1.410 (2) |
S2—O6 | 1.4286 (18) | O4—C3 | 1.412 (3) |
S2—O4 | 1.6126 (16) | O7—C5 | 1.408 (3) |
S2—C14 | 1.750 (2) | ||
O2—S1—O3 | 120.02 (11) | O4—S2—C14 | 104.58 (9) |
O2—S1—O1 | 109.00 (10) | O8—S3—O9 | 121.26 (11) |
O3—S1—O1 | 103.28 (10) | O8—S3—O7 | 108.56 (9) |
O2—S1—C7 | 108.25 (11) | O9—S3—O7 | 102.92 (9) |
O3—S1—C7 | 111.79 (11) | O8—S3—C21 | 110.11 (10) |
O1—S1—C7 | 103.05 (9) | O9—S3—C21 | 109.62 (10) |
O5—S2—O6 | 120.55 (11) | O7—S3—C21 | 102.52 (9) |
O5—S2—O4 | 102.78 (10) | C1—O1—S1 | 116.77 (13) |
O6—S2—O4 | 108.92 (9) | C3—O4—S2 | 118.57 (13) |
O5—S2—C14 | 109.67 (11) | C5—O7—S3 | 118.84 (13) |
O6—S2—C14 | 109.07 (11) | ||
C7—S1—O1—C1 | −57.22 (17) | C21—S3—O7—C5 | −90.20 (16) |
C14—S2—O4—C3 | 67.62 (17) |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···O2 | 0.89 (3) | 2.86 (2) | 3.122 (3) | 98.9 (18) |
C2—H2···O6 | 0.89 (3) | 2.58 (3) | 2.959 (3) | 106.9 (19) |
C8—H8···O3 | 0.94 (3) | 2.73 (3) | 3.049 (3) | 100.7 (18) |
C12—H12···O2 | 0.95 (3) | 2.51 (3) | 2.885 (3) | 104.0 (19) |
C15—H15···O6 | 0.96 (3) | 2.67 (3) | 2.976 (3) | 99.1 (17) |
C19—H19···O5 | 0.91 (3) | 2.53 (3) | 2.919 (3) | 106 (2) |
C22—H22···O8 | 0.90 (3) | 2.59 (3) | 2.934 (3) | 103.6 (18) |
C26—H26···O9 | 0.94 (3) | 2.70 (2) | 3.008 (3) | 100.4 (17) |
C2—H2···O3i | 0.89 (3) | 2.88 (3) | 3.529 (3) | 131 (2) |
C6—H6···O5ii | 0.92 (3) | 2.60 (3) | 3.494 (3) | 164 (2) |
C8—H8···O6ii | 0.94 (3) | 3.02 (3) | 3.540 (3) | 116.8 (19) |
C9—H9···O6ii | 0.94 (3) | 2.89 (3) | 3.488 (3) | 122.9 (19) |
C11—H11···O2iii | 0.92 (3) | 2.96 (3) | 3.725 (3) | 142 (2) |
C13—H13C···O6iii | 0.94 (3) | 2.98 (3) | 3.835 (3) | 151 (2) |
C18—H18···O4iv | 0.91 (3) | 2.94 (3) | 3.788 (3) | 156 (2) |
C18—H18···O9v | 0.91 (3) | 2.99 (3) | 3.531 (3) | 120 (2) |
C19—H19···O9v | 0.91 (3) | 2.67 (3) | 3.343 (3) | 131 (2) |
C20—H20A···O7vi | 0.90 (4) | 2.88 (4) | 3.701 (4) | 152 (3) |
C20—H20A···O9vi | 0.90 (4) | 2.82 (4) | 3.311 (3) | 116 (3) |
C20—H20C···O3iii | 0.95 (4) | 2.77 (4) | 3.670 (4) | 159 (3) |
C20—H20A···O9vi | 0.90 (4) | 2.82 (4) | 3.311 (3) | 116 (3) |
C23—H23···O5iv | 0.97 (3) | 2.70 (3) | 3.102 (3) | 105.4 (18) |
C25—H25···O1vi | 0.92 (3) | 2.94 (3) | 3.118 (3) | 92.5 (17) |
C25—H25···O2vii | 0.92 (3) | 2.42 (3) | 3.154 (3) | 136 (2) |
C26—H26···O2vii | 0.94 (3) | 2.92 (3) | 3.382 (3) | 112.1 (18) |
C27—H27A···O6vii | 0.99 (4) | 2.97 (4) | 3.958 (3) | 175 (3) |
C27—H27B···O3viii | 0.84 (4) | 2.71 (4) | 3.431 (4) | 145 (3) |
C27—H27C···O5iv | 0.98 (4) | 2.80 (4) | 3.455 (3) | 125 (3) |
C6—H6···Cg2 | 0.92 (3) | 3.26 | 3.576 | 102.5 |
C22—H22···Cg3 | 0.90 (3) | 2.86 | 3.638 | 145.2 |
C13—H13B···Cg3v | 0.97 (3) | 2.98 | 3.728 | 141.6 |
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) x+1, y, z; (iii) −x+2, −y+2, −z+1; (iv) −x+1, y+1/2, −z+1/2; (v) x−1, y, z; (vi) −x+2, y+1/2, −z+1/2; (vii) x, −y+3/2, z−1/2; (viii) x−1, −y+3/2, z−1/2. |
p-Toluene sulfonates 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.
The crystal structure is stabilized by weak C—H···O interactions (Table 2). The range for the H···O distances found in (I) agree with those found for weak C—H···O bonds (Desiraju & Steiner, 1999). The C2—H2···O2 and C2—H2···O6 interactions together constitute a pair of bifurcated donor bonds. Each generates a ring of graph set S(6) (Etter, 1990; Bernstein et al., 1995). Each of the C8—H8···O3, C12—H12···O2, C15—H15···O6, C19—H19···O5, C22—H22···O8 and C26—H26···O9 interactions generates S(5) ring motifs. The C8—H8···O6ii and C9—H9···O6ii interactions together form a pair of bifurcated acceptor bonds generating a ring of graph set R12(5) (Fig. 2; see Table 2 for symmetry codes). The C11—H11···O2iii and C13—H13C···O6iii interactions together generate a ring of graph set R22(14). A R22(20) motif is formed by the C11—H11···O2iii and C20—H20C···O3iii interactions. The C23—H23···O5iv and C27—H27C···O5iv (Fig. 3) interactions together form a pair of bifurcated acceptor bonds generating a ring of graph-set motif R12(6). The C18—H18···O9v and C19—H19···O9v (Fig. 2) interactions constitute a pair of bifurcated acceptor bonds generating a ring of graph set R12(5). The C20—H20A···O7vi and C20—H20A···O9vi interactions constitute a pair of bifurcated donor bonds generating a ring of graph set R21(4). The H20A···O7vi and H20A···O9vi distances differ by 0.06 (4) Å. The resulting configuration can be termed as a symmetrical three center hydrogen-bonded chelate (Desiraju, 1989) and is also observed in related structures (Vembu et al., 2003, 2003b,c,d,e). The C25—H25···O2vii and C26—H26···O2vii interactions together constitute a pair of bifurcated acceptor bonds generating a ring of graph set R12(5). There are several other C—H···O interactions which contribute for the supramolecular aggregation (Table 2).
The conformation of the molecule can be best described as a three legged table stabilized by the intramolecular C—H···O and C—H···π interactions. The atoms H12, O2, H2, O6, H15 form a `W'-shaped hydrogen-bonded chain which fix the S1 and S2 p-tolyl rings in almost similar dispostion with respect to the central benzene ring. This is also supported by the C6—H6···Cg2 interaction, where Cg1, Cg2, Cg3, and Cg4 are the centroids of the rings formed by C1—C6, C7—C12, C14—C19, and C21—C26 atoms, respectively. The S3 p-tolyl ring is not supported by a similar hydrogen-bonded network with the H atoms of the central benzene ring with special reference H4. This may be the reason for the nearly parallel orientation of the S3 p-tolyl ring with respect to the central benzene ring. In the crystal, the molecules are stacked in layers, held together by two π–π interactions. The distance between Cg1 and Cg4(-x, −1/2 + y, 1/2 − z) is 3.932 Å. The supramolecular aggregation is completed by the presence of three C—H···π interactions (Table 2), which were obtained from PLATON (Spek, 1998).