Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803013849/ob6263sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803013849/ob6263Isup2.hkl |
CCDC reference: 217609
Key indicators
- Single-crystal X-ray study
- T = 120 K
- Mean (C-C) = 0.004 Å
- R factor = 0.047
- wR factor = 0.112
- Data-to-parameter ratio = 17.0
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: 0.699 0.930 Tmin' and Tmax expected: 0.884 0.940 RR' = 0.800 Please check that your absorption correction is appropriate. General Notes
REFLT_03 From the CIF: _diffrn_reflns_theta_max 27.49 From the CIF: _reflns_number_total 6450 Count of symmetry unique reflns 3253 Completeness (_total/calc) 198.28% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 3197 Fraction of Friedel pairs measured 0.983 Are heavy atom types Z>Si present yes Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF.
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 2-naphthol (5.5 mmol) in aqueous NaOH (2.5 ml, 10%) with constant shaking. The precipitated compound, (I), (3.3 mmol, yield 70%) was filtered off and recrystallized from ethyl acetate.
Data collection: SMART-NT (Bruker, 1998); cell refinement: SMART-NT; data reduction: SAINT-NT (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.
C17H14O3S | F(000) = 624 |
Mr = 298.34 | Dx = 1.405 Mg m−3 |
Monoclinic, Pc | Melting point = 393–394 K |
Hall symbol: P -2yc | Mo Kα radiation, λ = 0.71073 Å |
a = 7.9315 (6) Å | Cell parameters from 942 reflections |
b = 29.130 (2) Å | θ = 2.9–27.4° |
c = 6.1111 (5) Å | µ = 0.24 mm−1 |
β = 92.383 (3)° | T = 120 K |
V = 1410.73 (19) Å3 | Block, colourless |
Z = 4 | 0.51 × 0.45 × 0.26 mm |
Bruker SMART 6K CCD area-detector diffractometer | 6450 independent reflections |
Radiation source: fine-focus sealed tube | 5907 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.045 |
Detector resolution: 8 pixels mm-1 | θmax = 27.5°, θmin = 0.7° |
ω scans | h = −10→10 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1998) | k = −37→37 |
Tmin = 0.699, Tmax = 0.930 | l = −7→7 |
20999 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.047 | H-atom parameters constrained |
wR(F2) = 0.112 | w = 1/[σ2(Fo2) + (0.0541P)2 + 0.7718P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.001 |
6450 reflections | Δρmax = 0.34 e Å−3 |
379 parameters | Δρmin = −0.32 e Å−3 |
2 restraints | Absolute structure: Flack (1983), 3197 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.03 (7) |
C17H14O3S | V = 1410.73 (19) Å3 |
Mr = 298.34 | Z = 4 |
Monoclinic, Pc | Mo Kα radiation |
a = 7.9315 (6) Å | µ = 0.24 mm−1 |
b = 29.130 (2) Å | T = 120 K |
c = 6.1111 (5) Å | 0.51 × 0.45 × 0.26 mm |
β = 92.383 (3)° |
Bruker SMART 6K CCD area-detector diffractometer | 6450 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1998) | 5907 reflections with I > 2σ(I) |
Tmin = 0.699, Tmax = 0.930 | Rint = 0.045 |
20999 measured reflections |
R[F2 > 2σ(F2)] = 0.047 | H-atom parameters constrained |
wR(F2) = 0.112 | Δρmax = 0.34 e Å−3 |
S = 1.04 | Δρmin = −0.32 e Å−3 |
6450 reflections | Absolute structure: Flack (1983), 3197 Friedel pairs |
379 parameters | Absolute structure parameter: 0.03 (7) |
2 restraints |
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 | 0.33101 (9) | 0.91865 (2) | 0.62202 (12) | 0.02686 (17) | |
O1 | 0.2236 (3) | 0.95769 (8) | 0.6089 (5) | 0.0413 (6) | |
O2 | 0.3813 (3) | 0.89919 (8) | 0.8286 (4) | 0.0358 (5) | |
O3 | 0.2264 (2) | 0.88092 (6) | 0.4804 (3) | 0.0242 (4) | |
C1 | 0.9502 (4) | 0.95299 (11) | 0.1037 (5) | 0.0317 (7) | |
H1A | 1.0503 | 0.9427 | 0.1893 | 0.048* | |
H1B | 0.9608 | 0.9858 | 0.0712 | 0.048* | |
H1C | 0.9403 | 0.9357 | −0.0337 | 0.048* | |
C2 | 0.7955 (3) | 0.94512 (9) | 0.2330 (5) | 0.0231 (6) | |
C3 | 0.8098 (3) | 0.92597 (10) | 0.4410 (5) | 0.0257 (6) | |
H3 | 0.9185 | 0.9188 | 0.5026 | 0.031* | |
C4 | 0.6674 (3) | 0.91706 (9) | 0.5620 (5) | 0.0218 (6) | |
H4 | 0.6780 | 0.9035 | 0.7032 | 0.026* | |
C5 | 0.5103 (3) | 0.92863 (9) | 0.4700 (5) | 0.0240 (6) | |
C6 | 0.4923 (3) | 0.94926 (9) | 0.2658 (5) | 0.0227 (6) | |
H6 | 0.3840 | 0.9579 | 0.2075 | 0.027* | |
C7 | 0.6353 (4) | 0.95703 (9) | 0.1487 (5) | 0.0250 (6) | |
H7 | 0.6240 | 0.9708 | 0.0079 | 0.030* | |
C8 | 0.2725 (3) | 0.83400 (9) | 0.5049 (5) | 0.0236 (6) | |
C9 | 0.3566 (3) | 0.81356 (10) | 0.3416 (5) | 0.0250 (6) | |
H9 | 0.3932 | 0.8310 | 0.2209 | 0.030* | |
C10 | 0.4719 (4) | 0.74204 (10) | 0.1904 (5) | 0.0285 (6) | |
H10 | 0.5111 | 0.7585 | 0.0684 | 0.034* | |
C11 | 0.4966 (4) | 0.69572 (11) | 0.2046 (6) | 0.0348 (7) | |
H11 | 0.5515 | 0.6802 | 0.0909 | 0.042* | |
C12 | 0.4414 (4) | 0.67065 (10) | 0.3860 (6) | 0.0345 (7) | |
H12 | 0.4598 | 0.6385 | 0.3939 | 0.041* | |
C13 | 0.3616 (4) | 0.69257 (11) | 0.5505 (5) | 0.0327 (7) | |
H13 | 0.3254 | 0.6756 | 0.6726 | 0.039* | |
C14 | 0.2474 (4) | 0.76440 (11) | 0.7044 (5) | 0.0292 (6) | |
H14 | 0.2116 | 0.7479 | 0.8282 | 0.035* | |
C15 | 0.2160 (4) | 0.81022 (10) | 0.6890 (5) | 0.0275 (6) | |
H15 | 0.1575 | 0.8258 | 0.7994 | 0.033* | |
C16 | 0.3889 (3) | 0.76536 (10) | 0.3555 (5) | 0.0239 (6) | |
C17 | 0.3324 (3) | 0.74101 (11) | 0.5395 (5) | 0.0258 (6) | |
S2 | 0.96993 (8) | 0.58200 (2) | 1.05639 (10) | 0.02009 (15) | |
O4 | 1.0857 (3) | 0.54516 (7) | 1.0349 (4) | 0.0304 (5) | |
O5 | 0.9319 (3) | 0.59901 (7) | 1.2672 (3) | 0.0277 (4) | |
O6 | 1.0545 (2) | 0.62248 (6) | 0.9197 (3) | 0.0218 (4) | |
C18 | 0.3206 (4) | 0.54824 (11) | 0.5314 (6) | 0.0311 (7) | |
H18A | 0.3437 | 0.5479 | 0.3751 | 0.037* | |
H18B | 0.2410 | 0.5730 | 0.5608 | 0.037* | |
H18C | 0.2717 | 0.5187 | 0.5725 | 0.037* | |
C19 | 0.4829 (3) | 0.55605 (9) | 0.6635 (5) | 0.0228 (5) | |
C20 | 0.6370 (4) | 0.54245 (10) | 0.5829 (5) | 0.0228 (6) | |
H20 | 0.6394 | 0.5279 | 0.4439 | 0.027* | |
C21 | 0.7874 (3) | 0.54989 (9) | 0.7032 (4) | 0.0209 (5) | |
H21 | 0.8921 | 0.5408 | 0.6468 | 0.025* | |
C22 | 0.7821 (3) | 0.57082 (9) | 0.9063 (4) | 0.0176 (5) | |
C23 | 0.6300 (3) | 0.58404 (9) | 0.9924 (5) | 0.0198 (5) | |
H23 | 0.6280 | 0.5980 | 1.1329 | 0.024* | |
C24 | 0.4813 (3) | 0.57660 (9) | 0.8703 (5) | 0.0235 (6) | |
H24 | 0.3768 | 0.5856 | 0.9279 | 0.028* | |
C25 | 0.9723 (3) | 0.66556 (9) | 0.9072 (5) | 0.0214 (5) | |
C26 | 0.9920 (3) | 0.69604 (9) | 1.0728 (5) | 0.0214 (5) | |
H26 | 1.0553 | 0.6880 | 1.2026 | 0.026* | |
C27 | 0.9356 (4) | 0.77356 (10) | 1.2172 (5) | 0.0273 (6) | |
H27 | 0.9988 | 0.7666 | 1.3483 | 0.033* | |
C28 | 0.8630 (4) | 0.81556 (11) | 1.1897 (6) | 0.0345 (7) | |
H28 | 0.8764 | 0.8379 | 1.3025 | 0.041* | |
C29 | 0.7676 (4) | 0.82664 (10) | 0.9956 (5) | 0.0339 (7) | |
H29 | 0.7162 | 0.8560 | 0.9810 | 0.041* | |
C30 | 0.7493 (4) | 0.79588 (11) | 0.8314 (5) | 0.0304 (7) | |
H30 | 0.6866 | 0.8039 | 0.7010 | 0.036* | |
C31 | 0.8066 (4) | 0.71786 (10) | 0.6864 (5) | 0.0251 (6) | |
H31 | 0.7431 | 0.7249 | 0.5555 | 0.030* | |
C32 | 0.8800 (3) | 0.67557 (10) | 0.7110 (5) | 0.0248 (6) | |
H32 | 0.8688 | 0.6533 | 0.5977 | 0.030* | |
C33 | 0.9165 (3) | 0.74073 (10) | 1.0508 (5) | 0.0218 (5) | |
C34 | 0.8242 (3) | 0.75096 (10) | 0.8527 (4) | 0.0235 (6) |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0179 (3) | 0.0275 (4) | 0.0356 (4) | −0.0036 (3) | 0.0065 (3) | −0.0112 (3) |
O1 | 0.0259 (12) | 0.0293 (12) | 0.0698 (18) | 0.0012 (9) | 0.0137 (11) | −0.0172 (11) |
O2 | 0.0303 (12) | 0.0499 (13) | 0.0275 (11) | −0.0133 (10) | 0.0051 (9) | −0.0088 (10) |
O3 | 0.0152 (9) | 0.0219 (9) | 0.0352 (11) | 0.0010 (7) | −0.0010 (8) | −0.0048 (8) |
C1 | 0.0234 (16) | 0.0359 (16) | 0.0364 (19) | −0.0058 (12) | 0.0080 (13) | 0.0011 (13) |
C2 | 0.0201 (13) | 0.0205 (12) | 0.0291 (15) | −0.0044 (10) | 0.0050 (11) | −0.0032 (11) |
C3 | 0.0148 (12) | 0.0298 (15) | 0.0323 (15) | 0.0010 (10) | −0.0009 (11) | 0.0015 (12) |
C4 | 0.0204 (13) | 0.0262 (14) | 0.0185 (13) | −0.0003 (10) | −0.0024 (10) | 0.0041 (10) |
C5 | 0.0183 (13) | 0.0201 (12) | 0.0340 (16) | −0.0010 (10) | 0.0057 (11) | −0.0072 (11) |
C6 | 0.0176 (12) | 0.0236 (13) | 0.0267 (14) | 0.0026 (10) | −0.0033 (11) | −0.0047 (11) |
C7 | 0.0278 (15) | 0.0219 (13) | 0.0254 (15) | −0.0023 (11) | 0.0007 (11) | 0.0002 (11) |
C8 | 0.0141 (12) | 0.0238 (13) | 0.0326 (15) | −0.0010 (10) | −0.0034 (11) | −0.0039 (11) |
C9 | 0.0186 (13) | 0.0298 (14) | 0.0268 (15) | −0.0042 (11) | 0.0020 (11) | −0.0013 (11) |
C10 | 0.0277 (15) | 0.0311 (15) | 0.0269 (15) | −0.0039 (12) | 0.0057 (12) | 0.0008 (12) |
C11 | 0.0358 (18) | 0.0282 (15) | 0.0409 (19) | 0.0013 (13) | 0.0090 (14) | −0.0018 (13) |
C12 | 0.0365 (18) | 0.0218 (14) | 0.046 (2) | 0.0013 (12) | 0.0098 (15) | 0.0010 (14) |
C13 | 0.0321 (17) | 0.0344 (16) | 0.0321 (16) | −0.0036 (13) | 0.0064 (13) | 0.0041 (13) |
C14 | 0.0247 (15) | 0.0390 (16) | 0.0244 (15) | −0.0043 (12) | 0.0052 (11) | 0.0020 (13) |
C15 | 0.0180 (13) | 0.0366 (16) | 0.0282 (15) | −0.0032 (11) | 0.0023 (11) | −0.0033 (12) |
C16 | 0.0196 (13) | 0.0293 (14) | 0.0229 (14) | −0.0041 (11) | 0.0024 (10) | 0.0008 (11) |
C17 | 0.0163 (13) | 0.0349 (16) | 0.0266 (15) | −0.0047 (11) | 0.0060 (11) | −0.0001 (12) |
S2 | 0.0150 (3) | 0.0223 (3) | 0.0228 (3) | 0.0003 (2) | −0.0006 (2) | 0.0012 (3) |
O4 | 0.0197 (10) | 0.0248 (11) | 0.0464 (14) | 0.0060 (8) | −0.0022 (9) | 0.0037 (9) |
O5 | 0.0258 (10) | 0.0322 (11) | 0.0250 (10) | −0.0045 (9) | 0.0003 (8) | 0.0006 (8) |
O6 | 0.0143 (9) | 0.0217 (9) | 0.0299 (10) | 0.0000 (7) | 0.0064 (7) | −0.0009 (8) |
C18 | 0.0245 (15) | 0.0320 (16) | 0.0360 (17) | −0.0044 (12) | −0.0093 (13) | 0.0061 (14) |
C19 | 0.0221 (13) | 0.0201 (13) | 0.0259 (14) | −0.0035 (10) | −0.0010 (11) | 0.0050 (11) |
C20 | 0.0267 (15) | 0.0210 (14) | 0.0210 (14) | −0.0028 (10) | 0.0041 (11) | 0.0000 (10) |
C21 | 0.0242 (13) | 0.0223 (13) | 0.0167 (13) | 0.0005 (10) | 0.0084 (10) | 0.0031 (10) |
C22 | 0.0131 (11) | 0.0194 (12) | 0.0201 (13) | −0.0014 (9) | −0.0031 (9) | 0.0053 (10) |
C23 | 0.0179 (13) | 0.0204 (12) | 0.0216 (13) | 0.0013 (9) | 0.0064 (10) | −0.0028 (10) |
C24 | 0.0152 (12) | 0.0251 (13) | 0.0305 (15) | 0.0027 (10) | 0.0045 (11) | 0.0023 (11) |
C25 | 0.0136 (12) | 0.0216 (12) | 0.0298 (15) | −0.0026 (9) | 0.0089 (10) | 0.0024 (11) |
C26 | 0.0158 (13) | 0.0264 (13) | 0.0221 (13) | −0.0027 (10) | 0.0029 (10) | 0.0020 (11) |
C27 | 0.0283 (15) | 0.0277 (15) | 0.0260 (15) | −0.0030 (12) | 0.0039 (12) | 0.0014 (12) |
C28 | 0.0434 (19) | 0.0257 (15) | 0.0350 (18) | −0.0017 (13) | 0.0066 (15) | −0.0004 (13) |
C29 | 0.0425 (19) | 0.0222 (14) | 0.0375 (18) | 0.0048 (12) | 0.0092 (15) | 0.0074 (12) |
C30 | 0.0324 (16) | 0.0316 (15) | 0.0274 (16) | −0.0014 (12) | 0.0051 (13) | 0.0056 (12) |
C31 | 0.0233 (14) | 0.0340 (15) | 0.0179 (13) | −0.0038 (11) | −0.0006 (10) | 0.0029 (11) |
C32 | 0.0219 (14) | 0.0298 (14) | 0.0230 (14) | −0.0048 (11) | 0.0050 (11) | −0.0002 (11) |
C33 | 0.0154 (12) | 0.0293 (14) | 0.0211 (13) | −0.0050 (10) | 0.0044 (10) | 0.0015 (11) |
C34 | 0.0194 (13) | 0.0311 (14) | 0.0204 (14) | −0.0038 (11) | 0.0059 (10) | 0.0044 (11) |
S1—O1 | 1.421 (2) | S2—O4 | 1.422 (2) |
S1—O2 | 1.426 (2) | S2—O5 | 1.424 (2) |
S1—O3 | 1.608 (2) | S2—O6 | 1.6076 (19) |
S1—C5 | 1.755 (3) | S2—C22 | 1.747 (3) |
O3—C8 | 1.421 (3) | O6—C25 | 1.415 (3) |
C1—C2 | 1.504 (4) | C18—C19 | 1.508 (4) |
C1—H1A | 0.9800 | C18—H18A | 0.9800 |
C1—H1B | 0.9800 | C18—H18B | 0.9800 |
C1—H1C | 0.9800 | C18—H18C | 0.9800 |
C2—C3 | 1.389 (4) | C19—C20 | 1.394 (4) |
C2—C7 | 1.395 (4) | C19—C24 | 1.399 (4) |
C3—C4 | 1.399 (4) | C20—C21 | 1.392 (4) |
C3—H3 | 0.9500 | C20—H20 | 0.9500 |
C4—C5 | 1.387 (4) | C21—C22 | 1.385 (4) |
C4—H4 | 0.9500 | C21—H21 | 0.9500 |
C5—C6 | 1.387 (4) | C22—C23 | 1.391 (4) |
C6—C7 | 1.385 (4) | C23—C24 | 1.386 (4) |
C6—H6 | 0.9500 | C23—H23 | 0.9500 |
C7—H7 | 0.9500 | C24—H24 | 0.9500 |
C8—C9 | 1.360 (4) | C25—C26 | 1.350 (4) |
C8—C15 | 1.410 (4) | C25—C32 | 1.409 (4) |
C9—C16 | 1.429 (4) | C26—C33 | 1.437 (4) |
C9—H9 | 0.9500 | C26—H26 | 0.9500 |
C10—C11 | 1.366 (4) | C27—C28 | 1.360 (4) |
C10—C16 | 1.403 (4) | C27—C33 | 1.399 (4) |
C10—H10 | 0.9500 | C27—H27 | 0.9500 |
C11—C12 | 1.413 (5) | C28—C29 | 1.417 (5) |
C11—H11 | 0.9500 | C28—H28 | 0.9500 |
C12—C13 | 1.368 (4) | C29—C30 | 1.349 (5) |
C12—H12 | 0.9500 | C29—H29 | 0.9500 |
C13—C17 | 1.431 (4) | C30—C34 | 1.441 (4) |
C13—H13 | 0.9500 | C30—H30 | 0.9500 |
C14—C15 | 1.361 (4) | C31—C32 | 1.368 (4) |
C14—C17 | 1.411 (4) | C31—C34 | 1.403 (4) |
C14—H14 | 0.9500 | C31—H31 | 0.9500 |
C15—H15 | 0.9500 | C32—H32 | 0.9500 |
C16—C17 | 1.418 (4) | C33—C34 | 1.420 (4) |
O1—S1—O2 | 120.88 (16) | O4—S2—O5 | 120.52 (14) |
O1—S1—O3 | 102.82 (13) | O4—S2—O6 | 102.75 (12) |
O2—S1—O3 | 108.90 (12) | O5—S2—O6 | 108.85 (11) |
O1—S1—C5 | 109.55 (14) | O4—S2—C22 | 110.52 (13) |
O2—S1—C5 | 109.36 (15) | O5—S2—C22 | 109.39 (12) |
O3—S1—C5 | 103.87 (12) | O6—S2—C22 | 103.24 (11) |
C8—O3—S1 | 118.41 (17) | C25—O6—S2 | 118.53 (15) |
C2—C1—H1A | 109.5 | C19—C18—H18A | 109.5 |
C2—C1—H1B | 109.5 | C19—C18—H18B | 109.5 |
H1A—C1—H1B | 109.5 | H18A—C18—H18B | 109.5 |
C2—C1—H1C | 109.5 | C19—C18—H18C | 109.5 |
H1A—C1—H1C | 109.5 | H18A—C18—H18C | 109.5 |
H1B—C1—H1C | 109.5 | H18B—C18—H18C | 109.5 |
C3—C2—C7 | 118.4 (3) | C20—C19—C24 | 118.8 (3) |
C3—C2—C1 | 120.3 (3) | C20—C19—C18 | 120.6 (3) |
C7—C2—C1 | 121.3 (3) | C24—C19—C18 | 120.5 (3) |
C2—C3—C4 | 121.4 (3) | C21—C20—C19 | 120.9 (3) |
C2—C3—H3 | 119.3 | C21—C20—H20 | 119.5 |
C4—C3—H3 | 119.3 | C19—C20—H20 | 119.5 |
C5—C4—C3 | 118.2 (3) | C22—C21—C20 | 119.0 (2) |
C5—C4—H4 | 120.9 | C22—C21—H21 | 120.5 |
C3—C4—H4 | 120.9 | C20—C21—H21 | 120.5 |
C6—C5—C4 | 121.8 (3) | C21—C22—C23 | 121.4 (2) |
C6—C5—S1 | 119.5 (2) | C21—C22—S2 | 119.7 (2) |
C4—C5—S1 | 118.6 (2) | C23—C22—S2 | 118.9 (2) |
C7—C6—C5 | 118.7 (3) | C24—C23—C22 | 119.0 (2) |
C7—C6—H6 | 120.7 | C24—C23—H23 | 120.5 |
C5—C6—H6 | 120.7 | C22—C23—H23 | 120.5 |
C6—C7—C2 | 121.5 (3) | C23—C24—C19 | 120.9 (2) |
C6—C7—H7 | 119.3 | C23—C24—H24 | 119.6 |
C2—C7—H7 | 119.3 | C19—C24—H24 | 119.6 |
C9—C8—C15 | 123.5 (3) | C26—C25—C32 | 122.8 (3) |
C9—C8—O3 | 118.4 (3) | C26—C25—O6 | 120.3 (3) |
C15—C8—O3 | 117.9 (2) | C32—C25—O6 | 116.9 (2) |
C8—C9—C16 | 118.6 (3) | C25—C26—C33 | 119.4 (3) |
C8—C9—H9 | 120.7 | C25—C26—H26 | 120.3 |
C16—C9—H9 | 120.7 | C33—C26—H26 | 120.3 |
C11—C10—C16 | 120.2 (3) | C28—C27—C33 | 119.5 (3) |
C11—C10—H10 | 119.9 | C28—C27—H27 | 120.2 |
C16—C10—H10 | 119.9 | C33—C27—H27 | 120.2 |
C10—C11—C12 | 120.8 (3) | C27—C28—C29 | 121.1 (3) |
C10—C11—H11 | 119.6 | C27—C28—H28 | 119.4 |
C12—C11—H11 | 119.6 | C29—C28—H28 | 119.4 |
C13—C12—C11 | 120.2 (3) | C30—C29—C28 | 120.6 (3) |
C13—C12—H12 | 119.9 | C30—C29—H29 | 119.7 |
C11—C12—H12 | 119.9 | C28—C29—H29 | 119.7 |
C12—C13—C17 | 120.3 (3) | C29—C30—C34 | 120.3 (3) |
C12—C13—H13 | 119.8 | C29—C30—H30 | 119.8 |
C17—C13—H13 | 119.8 | C34—C30—H30 | 119.8 |
C15—C14—C17 | 121.1 (3) | C32—C31—C34 | 120.7 (3) |
C15—C14—H14 | 119.5 | C32—C31—H31 | 119.7 |
C17—C14—H14 | 119.5 | C34—C31—H31 | 119.7 |
C14—C15—C8 | 118.3 (3) | C31—C32—C25 | 118.9 (3) |
C14—C15—H15 | 120.9 | C31—C32—H32 | 120.5 |
C8—C15—H15 | 120.9 | C25—C32—H32 | 120.5 |
C10—C16—C17 | 120.1 (3) | C27—C33—C34 | 120.8 (3) |
C10—C16—C9 | 121.4 (3) | C27—C33—C26 | 121.3 (3) |
C17—C16—C9 | 118.5 (3) | C34—C33—C26 | 117.9 (3) |
C14—C17—C16 | 120.1 (3) | C31—C34—C33 | 120.3 (3) |
C14—C17—C13 | 121.6 (3) | C31—C34—C30 | 122.0 (3) |
C16—C17—C13 | 118.3 (3) | C33—C34—C30 | 117.6 (3) |
O1—S1—O3—C8 | −163.2 (2) | O4—S2—O6—C25 | −179.4 (2) |
O2—S1—O3—C8 | −33.9 (2) | O5—S2—O6—C25 | −50.6 (2) |
C5—S1—O3—C8 | 82.6 (2) | C22—S2—O6—C25 | 65.6 (2) |
C7—C2—C3—C4 | 2.3 (4) | C24—C19—C20—C21 | −1.3 (4) |
C1—C2—C3—C4 | −178.1 (3) | C18—C19—C20—C21 | 179.5 (3) |
C2—C3—C4—C5 | −1.1 (4) | C19—C20—C21—C22 | 0.5 (4) |
C3—C4—C5—C6 | −1.2 (4) | C20—C21—C22—C23 | 0.6 (4) |
C3—C4—C5—S1 | −178.8 (2) | C20—C21—C22—S2 | −178.1 (2) |
O1—S1—C5—C6 | −42.8 (3) | O4—S2—C22—C21 | −39.0 (2) |
O2—S1—C5—C6 | −177.4 (2) | O5—S2—C22—C21 | −173.9 (2) |
O3—S1—C5—C6 | 66.5 (2) | O6—S2—C22—C21 | 70.3 (2) |
O1—S1—C5—C4 | 134.8 (2) | O4—S2—C22—C23 | 142.2 (2) |
O2—S1—C5—C4 | 0.2 (3) | O5—S2—C22—C23 | 7.3 (2) |
O3—S1—C5—C4 | −115.9 (2) | O6—S2—C22—C23 | −108.5 (2) |
C4—C5—C6—C7 | 2.1 (4) | C21—C22—C23—C24 | −0.9 (4) |
S1—C5—C6—C7 | 179.7 (2) | S2—C22—C23—C24 | 177.8 (2) |
C5—C6—C7—C2 | −0.8 (4) | C22—C23—C24—C19 | 0.1 (4) |
C3—C2—C7—C6 | −1.4 (4) | C20—C19—C24—C23 | 1.0 (4) |
C1—C2—C7—C6 | 179.1 (3) | C18—C19—C24—C23 | −179.8 (3) |
S1—O3—C8—C9 | −105.7 (3) | S2—O6—C25—C26 | 81.7 (3) |
S1—O3—C8—C15 | 79.5 (3) | S2—O6—C25—C32 | −102.1 (2) |
C15—C8—C9—C16 | 0.5 (4) | C32—C25—C26—C33 | 0.0 (4) |
O3—C8—C9—C16 | −174.0 (2) | O6—C25—C26—C33 | 176.0 (2) |
C16—C10—C11—C12 | −0.9 (5) | C33—C27—C28—C29 | 0.2 (5) |
C10—C11—C12—C13 | 0.2 (5) | C27—C28—C29—C30 | −1.2 (5) |
C11—C12—C13—C17 | 0.4 (5) | C28—C29—C30—C34 | 1.0 (5) |
C17—C14—C15—C8 | −0.8 (4) | C34—C31—C32—C25 | 0.6 (4) |
C9—C8—C15—C14 | 0.1 (4) | C26—C25—C32—C31 | −0.1 (4) |
O3—C8—C15—C14 | 174.6 (3) | O6—C25—C32—C31 | −176.2 (2) |
C11—C10—C16—C17 | 0.9 (5) | C28—C27—C33—C34 | 0.9 (4) |
C11—C10—C16—C9 | −178.0 (3) | C28—C27—C33—C26 | 179.6 (3) |
C8—C9—C16—C10 | 178.7 (3) | C25—C26—C33—C27 | −179.2 (3) |
C8—C9—C16—C17 | −0.3 (4) | C25—C26—C33—C34 | −0.4 (4) |
C15—C14—C17—C16 | 1.0 (4) | C32—C31—C34—C33 | −1.0 (4) |
C15—C14—C17—C13 | −178.0 (3) | C32—C31—C34—C30 | 179.7 (3) |
C10—C16—C17—C14 | −179.4 (3) | C27—C33—C34—C31 | 179.7 (3) |
C9—C16—C17—C14 | −0.4 (4) | C26—C33—C34—C31 | 0.9 (4) |
C10—C16—C17—C13 | −0.3 (4) | C27—C33—C34—C30 | −1.0 (4) |
C9—C16—C17—C13 | 178.6 (3) | C26—C33—C34—C30 | −179.8 (2) |
C12—C13—C17—C14 | 178.7 (3) | C29—C30—C34—C31 | 179.4 (3) |
C12—C13—C17—C16 | −0.3 (5) | C29—C30—C34—C33 | 0.0 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
C24—H24···O6i | 0.95 | 2.77 | 3.663 (3) | 157 |
C24—H24···O4i | 0.95 | 2.70 | 3.458 (4) | 138 |
C18—H18A···O4ii | 0.98 | 2.86 | 3.495 (4) | 124 |
C18—H18C···O4iii | 0.98 | 2.38 | 3.298 (4) | 156 |
C32—H32···O5iv | 0.95 | 2.63 | 3.549 (4) | 163 |
C21—H21···O5iv | 0.95 | 2.90 | 3.273 (3) | 105 |
C6—H6···O2iv | 0.95 | 2.88 | 3.138 (3) | 97 |
C6—H6···O1v | 0.95 | 2.82 | 3.555 (4) | 135 |
C1—H1B···O1vi | 0.98 | 2.66 | 3.386 (4) | 131 |
C1—H1A···O3vii | 0.98 | 2.85 | 3.753 (4) | 153 |
C3—H3···O3vii | 0.95 | 2.69 | 3.554 (3) | 152 |
C3—H3···O1vii | 0.95 | 2.73 | 3.521 (4) | 142 |
C26—H26···O5 | 0.95 | 2.80 | 3.111 (3) | 100 |
C23—H23···O5 | 0.95 | 2.51 | 2.900 (3) | 104 |
C21—H21···O4 | 0.95 | 2.77 | 3.054 (4) | 98 |
C15—H15···O2 | 0.95 | 2.78 | 3.012 (4) | 95 |
C6—H6···O1 | 0.95 | 2.81 | 3.061 (4) | 96 |
C4—H4···O2 | 0.95 | 2.51 | 2.895 (4) | 104 |
C7—H7···Cg1viii | 0.95 | 2.84 | 3.578 | 133 |
C10—H10···Cg6 | 0.95 | 2.74 | 3.383 | 121 |
C11—H11···Cg5 | 0.95 | 3.14 | 3.835 | 121 |
C14—H14···Cg5ix | 0.95 | 2.74 | 3.430 | 128 |
C15—H15···Cg6ix | 0.95 | 3.05 | 3.744 | 123 |
C20—H20···Cg4x | 0.95 | 2.82 | 3.574 | 138 |
C26—H26···Cg3vii | 0.95 | 3.15 | 3.806 | 128 |
C27—H27···Cg2vii | 0.95 | 2.63 | 3.415 | 132 |
C30—H30···Cg2iv | 0.95 | 3.23 | 3.956 | 138 |
C31—H31···Cg3iv | 0.95 | 2.84 | 3.582 | 132 |
Symmetry codes: (i) x−1, y, z; (ii) x−1, y, z−1; (iii) x−1, −y+1, z−1/2; (iv) x, y, z−1; (v) x, −y+2, z−1/2; (vi) x+1, −y+2, z−1/2; (vii) x+1, y, z; (viii) x, −y, z−1/2; (ix) x−1, y, z+1; (x) x, −y+1, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C17H14O3S |
Mr | 298.34 |
Crystal system, space group | Monoclinic, Pc |
Temperature (K) | 120 |
a, b, c (Å) | 7.9315 (6), 29.130 (2), 6.1111 (5) |
β (°) | 92.383 (3) |
V (Å3) | 1410.73 (19) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.24 |
Crystal size (mm) | 0.51 × 0.45 × 0.26 |
Data collection | |
Diffractometer | Bruker SMART 6K CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1998) |
Tmin, Tmax | 0.699, 0.930 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 20999, 6450, 5907 |
Rint | 0.045 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.047, 0.112, 1.04 |
No. of reflections | 6450 |
No. of parameters | 379 |
No. of restraints | 2 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.34, −0.32 |
Absolute structure | Flack (1983), 3197 Friedel pairs |
Absolute structure parameter | 0.03 (7) |
Computer programs: SMART-NT (Bruker, 1998), SMART-NT, SAINT-NT (Bruker, 1998), SHELXTL (Sheldrick, 1998), SHELXTL.
S1—O1 | 1.421 (2) | S1—C5 | 1.755 (3) |
S1—O2 | 1.426 (2) | O3—C8 | 1.421 (3) |
S1—O3 | 1.608 (2) | C1—C2 | 1.504 (4) |
O1—S1—O2 | 120.88 (16) | O4—S2—O5 | 120.52 (14) |
O1—S1—O3 | 102.82 (13) | O4—S2—O6 | 102.75 (12) |
O2—S1—O3 | 108.90 (12) | O5—S2—O6 | 108.85 (11) |
O1—S1—C5 | 109.55 (14) | O4—S2—C22 | 110.52 (13) |
O2—S1—C5 | 109.36 (15) | O5—S2—C22 | 109.39 (12) |
O3—S1—C5 | 103.87 (12) | O6—S2—C22 | 103.24 (11) |
C8—O3—S1 | 118.41 (17) | C25—O6—S2 | 118.53 (15) |
C5—S1—O3—C8 | 82.6 (2) | C22—S2—O6—C25 | 65.6 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C24—H24···O6i | 0.95 | 2.77 | 3.663 (3) | 156.6 |
C24—H24···O4i | 0.95 | 2.70 | 3.458 (4) | 137.6 |
C18—H18A···O4ii | 0.98 | 2.86 | 3.495 (4) | 123.5 |
C18—H18C···O4iii | 0.98 | 2.38 | 3.298 (4) | 155.7 |
C32—H32···O5iv | 0.95 | 2.63 | 3.549 (4) | 162.8 |
C21—H21···O5iv | 0.95 | 2.90 | 3.273 (3) | 104.6 |
C6—H6···O2iv | 0.95 | 2.88 | 3.138 (3) | 96.9 |
C6—H6···O1v | 0.95 | 2.82 | 3.555 (4) | 134.7 |
C1—H1B···O1vi | 0.98 | 2.66 | 3.386 (4) | 131.3 |
C1—H1A···O3vii | 0.98 | 2.85 | 3.753 (4) | 153.0 |
C3—H3···O3vii | 0.95 | 2.69 | 3.554 (3) | 152.0 |
C3—H3···O1vii | 0.95 | 2.73 | 3.521 (4) | 141.7 |
C26—H26···O5 | 0.95 | 2.80 | 3.111 (3) | 99.8 |
C23—H23···O5 | 0.95 | 2.51 | 2.900 (3) | 104.4 |
C21—H21···O4 | 0.95 | 2.77 | 3.054 (4) | 97.9 |
C15—H15···O2 | 0.95 | 2.78 | 3.012 (4) | 94.8 |
C6—H6···O1 | 0.95 | 2.81 | 3.061 (4) | 96.1 |
C4—H4···O2 | 0.95 | 2.51 | 2.895 (4) | 104.4 |
C7—H7···Cg1viii | 0.95 | 2.843 | 3.578 | 133.12 |
C10—H10···Cg6 | 0.95 | 2.740 | 3.383 | 121.43 |
C11—H11···Cg5 | 0.95 | 3.143 | 3.835 | 121.23 |
C14—H14···Cg5ix | 0.95 | 2.736 | 3.430 | 127.69 |
C15—H15···Cg6ix | 0.95 | 3.045 | 3.744 | 123.31 |
C20—H20···Cg4x | 0.95 | 2.823 | 3.574 | 137.73 |
C26—H26···Cg3vii | 0.95 | 3.146 | 3.806 | 128.31 |
C27—H27···Cg2vii | 0.95 | 2.626 | 3.415 | 131.63 |
C30—H30···Cg2iv | 0.95 | 3.231 | 3.956 | 137.57 |
C31—H31···Cg3iv | 0.95 | 2.844 | 3.582 | 131.56 |
Symmetry codes: (i) x−1, y, z; (ii) x−1, y, z−1; (iii) x−1, −y+1, z−1/2; (iv) x, y, z−1; (v) x, −y+2, z−1/2; (vi) x+1, −y+2, z−1/2; (vii) x+1, y, z; (viii) x, −y, z−1/2; (ix) x−1, y, z+1; (x) x, −y+1, z−1/2. |
p-Toluene sulfonates are used in monitoring the merging of lipids (Yachi et al., 1989), studying membrane fusion during acrosome reactions (Spungin et al., 1992), development of immuno-affinity 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 photosensitizers to model monoclonal antibodies (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 because of the biological importance of its analogues.
The dihedral angle between the mean planes of the 4-tolyl and 2-naphthyl rings is 65.10 (7)° for the molecule involving S1, and 55.11 (7)° for the molecule involving S2 (Fig. 1 and Table 1). This shows their non-coplanar orientation, similar to that found between the 4-tolyl and 2-chlorophenyl rings in 2-chlorophenyl 4-toluenesulfonate (Vembu, Nallu, Garrison & Youngs, 2003b) and the 4-tolyl and quinoline rings in 8-tosyloxyquinoline (Vembu, Nallu, Garrison & Youngs, 2003c) and in contrast to the near coplanar orientation of the 4-tolyl and 2,4-dinitrophenyl rings in 2,4-dinitrophenyl 4-toluenesulfonate (Vembu, Nallu, Garrison & Youngs, 2003a) and 4-tolyl and 4-methoxyphenyl rings in 4-methoxyphenyl 4-toluenesulfonate (Vembu, Nallu, Garrison, Hindi & Youngs, 2003).
The crystal structure of (I) is stabilized by weak C—H···O interactions. The range of H···O distances (Table 2) agrees with that found for weak C—H···O bonds (Desiraju & Steiner, 1999). The C4—H4···O2, C6—H6···O1, C15—H15···O2 (Fig.2), C21—H21···O4, C23—H23···O5 and C26—H26···O5 intramolecular interactions generate rings of graph-set motif (Etter, 1990; Bernstein et al., 1995) S(5), S(5), S(6), S(5), S(5) and S(6), respectively. The C3—H3···O1vii and C3—H3···O3vii interactions constitute a pair of bifurcated donor bonds, generating a ring of graph set R21(4). The H3···O1vii and H3···O3vii distances differ only by 0.04 Å. The resulting configuration is best regarded as a three-centered symmetrical hydrogen-bonded chelate motif (Desiraju, 1989) and is also observed in similar structures (Vembu, Nallu, Garrison & Youngs, 2003b, 2003c, 2003 d,2003 e, 2003f, 2003 g; Vembu, Nallu, Garrison, Hindi & Youngs 2003). The C3—H3···O3vii and C1—H1A···O3vii interactions constitute a pair of bifurcated acceptor bonds, generating a ring of graph set R12(6). The C3—H3···O1vii and C1—H1A···O3vii interactions together generate a ring of graph set R12(8). The R21(4) chelate motif and the R12(6) ring motif are present within the R12(8) ring motif. The C21—H21···O5iv and C32—H32···O5iv interactions constitute a pair of bifurcated acceptor bonds, generating a ring of graph set R12(9). The C24—H24···O4i and C24—H24···O6i (Fig.3) interactions constitute a pair of bifurcated donor bonds, forming another symmetrical three[centered hydrogen-bonded chelate motif of graph set R21(4). The H24···O4i and H24···O6i distances differ by 0.07 Å. There are several other weak C—H···O bonds (Table 2, Fig. 3), which contribute to the aggregation of the title compound in the crystal lattice. The supramolecular aggregation is completed by the presence of ten C—H···π interactions (Table 2), where Cg1–Cg6 are the centroids of the rings C2—C7, C8—C9/C14—C17, C10—C13/C16—C17, C19—C24, C25—C26/C31—C34 and C27—C30/C33—C34, respectively. The details of these C—H···π interactions were calculated using PLATON (Spek, 1998).