Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807023859/hk2239sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807023859/hk2239Isup2.hkl |
CCDC reference: 651497
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.010 Å
- R factor = 0.054
- wR factor = 0.116
- Data-to-parameter ratio = 8.0
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 1.02 PLAT230_ALERT_2_C Hirshfeld Test Diff for S1 - O1 .. 5.02 su PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 10
Alert level G REFLT03_ALERT_4_G WARNING: Large fraction of Friedel related reflns may be needed to determine absolute structure From the CIF: _diffrn_reflns_theta_max 25.95 From the CIF: _reflns_number_total 2890 Count of symmetry unique reflns 2888 Completeness (_total/calc) 100.07% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 2 Fraction of Friedel pairs measured 0.001 Are heavy atom types Z>Si present yes PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 202
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
2,2'-ethylidenebis(4-methylPhenol)(1.21 g, 5 mmol) and triethylamine (11 mmol, 1.52 ml) and methylene chloride(AR) (100 ml) were added into the four-neck round-bottom flask fitted with a mechanical stirrer, dropping funnel, thermometer, and reflux condenser. The system was put in an ice-water bath and stirred for 30 min. and then thionyl chloride (5 mmol, 0.36 ml) which was dissolved in methylene chloride(AR) (50 ml) was added and stirred. The reaction was kept at 273 K in an ice-water bath for 24 h. The mixture was washed with hydrogen chloride solution (5%, 100 ml) and saturated sodium hydrogen carbonate (7.4%, 100 ml) and distilled water (200 ml). The solvent was distilled under reduced pressure. The residue was exsiccated in a desiccator. The product was purified by repeated crystallization. Crystals of (I) suitable for X-ray analysis were obtained by slow evaporation of isopropyl alcohol(AR) (10 ml) (yield; 1.04 g, 72%, m.p. 401 K).
H atoms were positioned geometrically, with C—H = 0.93, 0.98 and 0.96 Å for aromatic, methine and methyl H, respectively, and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C), where x = 1.5 for methyl H, and x = 1.2 for all other H atoms.
In a research for novel antioxidants, a series of medium-ring heterocycles derived from sterically hindered phenols has been prepared and investigated (Pastor et al., 1983). We herein report the crystal structure of the title compound, (I).
The asymmetric unit of (I) contains two independent molecules, essentially in the same geometry (Fig. 1). The bond lengths and angles (Table 1) are within normal ranges (Allen et al., 1987).
Rings A(C2—C7), B(C9—C14), D(C18—C23) and E(C25—C30) are, of course, planar and the dihedral angles between them are A/B = 79.06 (2)° and D/E=78.46 (2)°. Rings C (S1/O2/O3/C4/C5/C12/C13/C15) and F (S2/O5/O6/C21/C22/C27/C28/C31) are not planar, having total puckering amplitudes, QT, of 1.057 (3) and 1.037 (3) Å, respectively, and boat-chair conformations (Cremer & Pople, 1975).
For general backgroud, see: Pastor et al. (1983); Allen et al. (1987); Cremer & Pople (1975).
Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.
Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 15% probability level. |
C16H16O3S | Dx = 1.323 Mg m−3 |
Mr = 288.36 | Melting point: 401 K |
Orthorhombic, Pca21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2ac | Cell parameters from 25 reflections |
a = 14.122 (3) Å | θ = 10–13° |
b = 8.0880 (16) Å | µ = 0.23 mm−1 |
c = 25.343 (5) Å | T = 298 K |
V = 2894.6 (10) Å3 | Block, colorless |
Z = 8 | 0.30 × 0.20 × 0.10 mm |
F(000) = 1216 |
Enraf–Nonius CAD-4 diffractometer | 1444 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.021 |
Graphite monochromator | θmax = 26.0°, θmin = 1.6° |
ω/2θ scans | h = 0→17 |
Absorption correction: ψ scan (North et al., 1968) | k = 0→9 |
Tmin = 0.915, Tmax = 0.958 | l = −31→0 |
3213 measured reflections | 3 standard reflections every 200 reflections |
2890 independent reflections | intensity decay: none |
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)] = 0.054 | H-atom parameters constrained |
wR(F2) = 0.116 | w = 1/[σ2(Fo2) + (0.040P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.00 | (Δ/σ)max < 0.001 |
2890 reflections | Δρmax = 0.31 e Å−3 |
361 parameters | Δρmin = −0.14 e Å−3 |
202 restraints | Absolute structure: Flack (1983), 208 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.06 (17) |
C16H16O3S | V = 2894.6 (10) Å3 |
Mr = 288.36 | Z = 8 |
Orthorhombic, Pca21 | Mo Kα radiation |
a = 14.122 (3) Å | µ = 0.23 mm−1 |
b = 8.0880 (16) Å | T = 298 K |
c = 25.343 (5) Å | 0.30 × 0.20 × 0.10 mm |
Enraf–Nonius CAD-4 diffractometer | 1444 reflections with I > 2σ(I) |
Absorption correction: ψ scan (North et al., 1968) | Rint = 0.021 |
Tmin = 0.915, Tmax = 0.958 | 3 standard reflections every 200 reflections |
3213 measured reflections | intensity decay: none |
2890 independent reflections |
R[F2 > 2σ(F2)] = 0.054 | H-atom parameters constrained |
wR(F2) = 0.116 | Δρmax = 0.31 e Å−3 |
S = 1.00 | Δρmin = −0.14 e Å−3 |
2890 reflections | Absolute structure: Flack (1983), 208 Friedel pairs |
361 parameters | Absolute structure parameter: −0.06 (17) |
202 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 | 0.21883 (16) | 0.7088 (3) | 0.74303 (10) | 0.0973 (7) | |
O1 | 0.1300 (4) | 0.7391 (6) | 0.7223 (2) | 0.1098 (19) | |
O2 | 0.2261 (3) | 0.8052 (6) | 0.7991 (2) | 0.0862 (16) | |
O3 | 0.2965 (3) | 0.8038 (6) | 0.7086 (2) | 0.0833 (15) | |
C1 | 0.0108 (6) | 1.3898 (10) | 0.8340 (3) | 0.116 (3) | |
H1B | −0.0482 | 1.3606 | 0.8503 | 0.175* | |
H1C | −0.0013 | 1.4450 | 0.8011 | 0.175* | |
H1D | 0.0456 | 1.4622 | 0.8570 | 0.175* | |
C2 | 0.0693 (5) | 1.2320 (9) | 0.8237 (3) | 0.0788 (19) | |
C3 | 0.1592 (4) | 1.2418 (8) | 0.8007 (3) | 0.0655 (18) | |
H3A | 0.1826 | 1.3447 | 0.7906 | 0.079* | |
C4 | 0.2138 (5) | 1.1037 (9) | 0.7925 (3) | 0.0617 (18) | |
C5 | 0.1728 (5) | 0.9516 (10) | 0.8060 (3) | 0.0694 (19) | |
C6 | 0.0842 (5) | 0.9431 (10) | 0.8286 (3) | 0.083 (2) | |
H6A | 0.0590 | 0.8416 | 0.8385 | 0.099* | |
C7 | 0.0340 (5) | 1.0837 (10) | 0.8362 (3) | 0.084 (2) | |
H7A | −0.0266 | 1.0770 | 0.8505 | 0.101* | |
C8 | 0.2456 (6) | 1.3871 (9) | 0.5856 (3) | 0.102 (2) | |
H8A | 0.2534 | 1.4839 | 0.6071 | 0.152* | |
H8B | 0.1839 | 1.3883 | 0.5697 | 0.152* | |
H8C | 0.2931 | 1.3861 | 0.5584 | 0.152* | |
C9 | 0.2561 (4) | 1.2314 (8) | 0.6201 (3) | 0.0676 (16) | |
C10 | 0.2452 (5) | 1.0780 (9) | 0.5978 (3) | 0.0739 (19) | |
H10A | 0.2296 | 1.0695 | 0.5622 | 0.089* | |
C11 | 0.2570 (5) | 0.9372 (9) | 0.6271 (3) | 0.0762 (18) | |
H11A | 0.2511 | 0.8337 | 0.6115 | 0.091* | |
C12 | 0.2775 (4) | 0.9505 (9) | 0.6798 (3) | 0.0689 (18) | |
C13 | 0.2884 (4) | 1.1028 (9) | 0.7053 (3) | 0.0580 (17) | |
C14 | 0.2783 (4) | 1.2404 (8) | 0.6728 (3) | 0.0675 (18) | |
H14A | 0.2871 | 1.3445 | 0.6876 | 0.081* | |
C15 | 0.3078 (4) | 1.1142 (9) | 0.7630 (3) | 0.0660 (19) | |
H15A | 0.3439 | 1.0152 | 0.7725 | 0.079* | |
C16 | 0.3669 (4) | 1.2611 (7) | 0.7795 (3) | 0.082 (2) | |
H16A | 0.4262 | 1.2589 | 0.7610 | 0.122* | |
H16B | 0.3783 | 1.2563 | 0.8168 | 0.122* | |
H16C | 0.3337 | 1.3613 | 0.7711 | 0.122* | |
S2 | 0.04866 (15) | 0.7149 (3) | 0.51953 (10) | 0.0912 (6) | |
O4 | 0.1369 (4) | 0.7467 (6) | 0.5400 (2) | 0.1101 (19) | |
O5 | −0.0329 (3) | 0.8073 (6) | 0.5539 (2) | 0.0810 (15) | |
O6 | 0.0424 (3) | 0.8172 (6) | 0.4638 (2) | 0.0813 (16) | |
C17 | 0.2390 (6) | 1.4193 (10) | 0.4275 (3) | 0.109 (3) | |
H17A | 0.2000 | 1.5103 | 0.4385 | 0.163* | |
H17B | 0.2535 | 1.4303 | 0.3907 | 0.163* | |
H17C | 0.2966 | 1.4192 | 0.4476 | 0.163* | |
C18 | 0.1868 (5) | 1.2598 (8) | 0.4366 (3) | 0.0731 (18) | |
C19 | 0.2286 (5) | 1.1054 (10) | 0.4249 (3) | 0.080 (2) | |
H19A | 0.2899 | 1.1010 | 0.4115 | 0.096* | |
C20 | 0.1795 (6) | 0.9635 (11) | 0.4330 (3) | 0.081 (2) | |
H20A | 0.2053 | 0.8631 | 0.4223 | 0.097* | |
C21 | 0.0904 (5) | 0.9661 (9) | 0.4573 (3) | 0.0665 (18) | |
C22 | 0.0483 (5) | 1.1173 (9) | 0.4706 (3) | 0.0664 (19) | |
C23 | 0.0994 (5) | 1.2595 (8) | 0.4597 (3) | 0.0716 (18) | |
H23A | 0.0725 | 1.3607 | 0.4685 | 0.086* | |
C24 | 0.0153 (5) | 1.3952 (9) | 0.6739 (3) | 0.093 (2) | |
H24A | 0.0061 | 1.4887 | 0.6511 | 0.140* | |
H24B | 0.0772 | 1.4006 | 0.6894 | 0.140* | |
H24C | −0.0317 | 1.3965 | 0.7013 | 0.140* | |
C25 | 0.0060 (4) | 1.2366 (9) | 0.6420 (3) | 0.0734 (18) | |
C26 | −0.0158 (4) | 1.2464 (7) | 0.5889 (3) | 0.0636 (17) | |
H26A | −0.0231 | 1.3501 | 0.5736 | 0.076* | |
C27 | −0.0273 (4) | 1.1081 (10) | 0.5581 (3) | 0.0679 (19) | |
C28 | −0.0154 (4) | 0.9546 (9) | 0.5820 (3) | 0.0642 (17) | |
C29 | 0.0086 (5) | 0.9411 (10) | 0.6343 (3) | 0.0750 (19) | |
H29A | 0.0189 | 0.8378 | 0.6493 | 0.090* | |
C30 | 0.0170 (4) | 1.0803 (10) | 0.6639 (3) | 0.0755 (19) | |
H30A | 0.0305 | 1.0707 | 0.6997 | 0.091* | |
C31 | −0.0445 (4) | 1.1191 (8) | 0.4987 (3) | 0.0640 (18) | |
H31A | −0.0772 | 1.0169 | 0.4886 | 0.077* | |
C32 | −0.1105 (4) | 1.2619 (8) | 0.4832 (3) | 0.083 (2) | |
H32A | −0.1209 | 1.2601 | 0.4458 | 0.124* | |
H32B | −0.0820 | 1.3652 | 0.4930 | 0.124* | |
H32C | −0.1700 | 1.2498 | 0.5012 | 0.124* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0971 (16) | 0.0757 (12) | 0.119 (2) | −0.0127 (12) | 0.0042 (14) | −0.0001 (15) |
O1 | 0.127 (5) | 0.085 (4) | 0.118 (4) | −0.020 (3) | −0.003 (4) | −0.007 (3) |
O2 | 0.108 (4) | 0.070 (3) | 0.080 (4) | 0.003 (3) | 0.000 (3) | 0.015 (3) |
O3 | 0.072 (3) | 0.077 (3) | 0.101 (4) | 0.010 (3) | 0.005 (3) | 0.007 (3) |
C1 | 0.108 (6) | 0.130 (7) | 0.111 (7) | 0.025 (6) | 0.030 (6) | 0.014 (6) |
C2 | 0.074 (4) | 0.089 (4) | 0.073 (4) | 0.009 (4) | −0.011 (3) | −0.001 (4) |
C3 | 0.072 (4) | 0.064 (4) | 0.060 (4) | −0.007 (3) | 0.007 (3) | 0.002 (3) |
C4 | 0.057 (4) | 0.068 (4) | 0.061 (4) | 0.001 (3) | −0.017 (3) | 0.005 (4) |
C5 | 0.072 (4) | 0.075 (4) | 0.061 (5) | −0.010 (4) | −0.001 (3) | 0.014 (4) |
C6 | 0.080 (4) | 0.084 (4) | 0.084 (5) | −0.015 (4) | 0.004 (4) | −0.002 (4) |
C7 | 0.065 (4) | 0.107 (5) | 0.081 (5) | −0.005 (4) | 0.002 (4) | 0.000 (5) |
C8 | 0.098 (5) | 0.105 (5) | 0.101 (5) | 0.014 (5) | 0.007 (5) | 0.012 (4) |
C9 | 0.054 (3) | 0.079 (4) | 0.071 (4) | −0.003 (3) | 0.002 (3) | 0.013 (3) |
C10 | 0.058 (4) | 0.088 (4) | 0.075 (4) | −0.004 (4) | 0.009 (4) | −0.008 (4) |
C11 | 0.061 (4) | 0.077 (4) | 0.091 (4) | −0.006 (4) | 0.012 (4) | −0.014 (4) |
C12 | 0.051 (4) | 0.059 (3) | 0.096 (5) | 0.002 (3) | 0.002 (4) | −0.008 (4) |
C13 | 0.044 (3) | 0.068 (4) | 0.062 (4) | −0.001 (3) | 0.005 (3) | 0.003 (3) |
C14 | 0.055 (4) | 0.068 (4) | 0.079 (4) | −0.007 (3) | 0.002 (3) | 0.001 (3) |
C15 | 0.039 (3) | 0.070 (4) | 0.090 (5) | 0.000 (3) | −0.008 (3) | 0.012 (4) |
C16 | 0.066 (4) | 0.074 (5) | 0.105 (6) | −0.007 (4) | −0.015 (4) | −0.005 (4) |
S2 | 0.0892 (15) | 0.0773 (12) | 0.1071 (16) | 0.0089 (12) | 0.0064 (14) | 0.0016 (14) |
O4 | 0.116 (5) | 0.089 (4) | 0.126 (5) | 0.022 (3) | −0.005 (4) | −0.009 (3) |
O5 | 0.064 (3) | 0.068 (3) | 0.110 (4) | −0.007 (3) | 0.009 (3) | −0.005 (3) |
O6 | 0.073 (3) | 0.072 (3) | 0.099 (4) | 0.006 (3) | −0.016 (3) | −0.016 (3) |
C17 | 0.105 (6) | 0.116 (6) | 0.105 (6) | −0.050 (5) | 0.003 (5) | 0.004 (5) |
C18 | 0.079 (4) | 0.083 (4) | 0.058 (4) | −0.009 (4) | 0.012 (3) | −0.010 (3) |
C19 | 0.074 (4) | 0.103 (5) | 0.064 (4) | 0.009 (4) | 0.021 (4) | 0.010 (4) |
C20 | 0.085 (4) | 0.089 (4) | 0.069 (5) | 0.023 (4) | 0.004 (4) | −0.001 (4) |
C21 | 0.067 (4) | 0.069 (4) | 0.064 (4) | −0.004 (3) | −0.014 (3) | −0.011 (4) |
C22 | 0.057 (4) | 0.069 (4) | 0.073 (5) | 0.000 (3) | 0.000 (3) | −0.011 (4) |
C23 | 0.067 (4) | 0.071 (4) | 0.077 (4) | −0.004 (3) | 0.002 (3) | −0.006 (4) |
C24 | 0.086 (5) | 0.111 (6) | 0.083 (5) | −0.002 (5) | 0.002 (4) | −0.035 (5) |
C25 | 0.054 (4) | 0.088 (4) | 0.078 (4) | −0.010 (4) | 0.005 (3) | 0.000 (4) |
C26 | 0.060 (4) | 0.049 (3) | 0.082 (4) | −0.005 (3) | 0.001 (3) | 0.004 (3) |
C27 | 0.044 (3) | 0.080 (4) | 0.080 (5) | 0.001 (3) | −0.005 (3) | −0.004 (4) |
C28 | 0.050 (3) | 0.063 (4) | 0.079 (4) | −0.003 (3) | 0.010 (3) | −0.005 (4) |
C29 | 0.060 (4) | 0.086 (4) | 0.079 (4) | −0.003 (4) | 0.004 (4) | 0.007 (4) |
C30 | 0.054 (4) | 0.099 (5) | 0.073 (4) | 0.000 (4) | −0.003 (3) | 0.006 (4) |
C31 | 0.057 (4) | 0.048 (4) | 0.087 (5) | 0.000 (3) | −0.013 (4) | −0.006 (3) |
C32 | 0.053 (4) | 0.087 (5) | 0.108 (6) | 0.009 (4) | −0.025 (4) | −0.005 (4) |
S1—O1 | 1.381 (5) | S2—O4 | 1.375 (5) |
S1—O3 | 1.599 (5) | S2—O5 | 1.626 (5) |
S1—O2 | 1.625 (6) | S2—O6 | 1.639 (6) |
O2—C5 | 1.414 (8) | O5—C28 | 1.410 (8) |
O3—C12 | 1.418 (9) | O6—C21 | 1.391 (8) |
C1—C2 | 1.542 (9) | C17—C18 | 1.503 (9) |
C1—H1B | 0.9600 | C17—H17A | 0.9600 |
C1—H1C | 0.9600 | C17—H17B | 0.9600 |
C1—H1D | 0.9600 | C17—H17C | 0.9600 |
C2—C7 | 1.337 (9) | C18—C23 | 1.366 (9) |
C2—C3 | 1.400 (9) | C18—C19 | 1.413 (9) |
C3—C4 | 1.374 (8) | C19—C20 | 1.357 (10) |
C3—H3A | 0.9300 | C19—H19A | 0.9300 |
C4—C5 | 1.403 (10) | C20—C21 | 1.401 (10) |
C4—C15 | 1.525 (8) | C20—H20A | 0.9300 |
C5—C6 | 1.377 (10) | C21—C22 | 1.401 (9) |
C6—C7 | 1.353 (10) | C22—C23 | 1.385 (9) |
C6—H6A | 0.9300 | C22—C31 | 1.491 (9) |
C7—H7A | 0.9300 | C23—H23A | 0.9300 |
C8—C9 | 1.541 (9) | C24—C25 | 1.522 (9) |
C8—H8A | 0.9600 | C24—H24A | 0.9600 |
C8—H8B | 0.9600 | C24—H24B | 0.9600 |
C8—H8C | 0.9600 | C24—H24C | 0.9600 |
C9—C10 | 1.373 (8) | C25—C26 | 1.383 (9) |
C9—C14 | 1.374 (9) | C25—C30 | 1.389 (9) |
C10—C11 | 1.371 (9) | C26—C27 | 1.374 (9) |
C10—H10A | 0.9300 | C26—H26A | 0.9300 |
C11—C12 | 1.370 (10) | C27—C28 | 1.392 (10) |
C11—H11A | 0.9300 | C27—C31 | 1.528 (10) |
C12—C13 | 1.399 (10) | C28—C29 | 1.371 (9) |
C13—C14 | 1.392 (9) | C29—C30 | 1.358 (9) |
C13—C15 | 1.491 (10) | C29—H29A | 0.9300 |
C14—H14A | 0.9300 | C30—H30A | 0.9300 |
C15—C16 | 1.511 (8) | C31—C32 | 1.536 (8) |
C15—H15A | 0.9800 | C31—H31A | 0.9800 |
C16—H16A | 0.9600 | C32—H32A | 0.9600 |
C16—H16B | 0.9600 | C32—H32B | 0.9600 |
C16—H16C | 0.9600 | C32—H32C | 0.9600 |
O1—S1—O3 | 109.3 (3) | O4—S2—O5 | 110.7 (3) |
O1—S1—O2 | 107.7 (3) | O4—S2—O6 | 106.2 (3) |
O3—S1—O2 | 101.8 (3) | O5—S2—O6 | 101.0 (3) |
C5—O2—S1 | 118.4 (5) | C28—O5—S2 | 122.3 (4) |
C12—O3—S1 | 123.6 (4) | C21—O6—S2 | 120.8 (5) |
C2—C1—H1B | 109.5 | C18—C17—H17A | 109.5 |
C2—C1—H1C | 109.5 | C18—C17—H17B | 109.5 |
H1B—C1—H1C | 109.5 | H17A—C17—H17B | 109.5 |
C2—C1—H1D | 109.5 | C18—C17—H17C | 109.5 |
H1B—C1—H1D | 109.5 | H17A—C17—H17C | 109.5 |
H1C—C1—H1D | 109.5 | H17B—C17—H17C | 109.5 |
C7—C2—C3 | 119.2 (7) | C23—C18—C19 | 117.8 (6) |
C7—C2—C1 | 120.2 (7) | C23—C18—C17 | 120.6 (7) |
C3—C2—C1 | 120.6 (7) | C19—C18—C17 | 121.5 (7) |
C4—C3—C2 | 121.8 (6) | C20—C19—C18 | 120.1 (7) |
C4—C3—H3A | 119.1 | C20—C19—H19A | 119.9 |
C2—C3—H3A | 119.1 | C18—C19—H19A | 119.9 |
C3—C4—C5 | 116.4 (7) | C19—C20—C21 | 120.9 (8) |
C3—C4—C15 | 121.2 (7) | C19—C20—H20A | 119.6 |
C5—C4—C15 | 121.9 (7) | C21—C20—H20A | 119.6 |
C6—C5—C4 | 121.4 (7) | O6—C21—C22 | 121.4 (6) |
C6—C5—O2 | 119.6 (7) | O6—C21—C20 | 118.4 (7) |
C4—C5—O2 | 118.9 (6) | C22—C21—C20 | 120.0 (7) |
C7—C6—C5 | 119.5 (8) | C23—C22—C21 | 117.1 (6) |
C7—C6—H6A | 120.2 | C23—C22—C31 | 123.0 (7) |
C5—C6—H6A | 120.2 | C21—C22—C31 | 119.7 (7) |
C2—C7—C6 | 121.6 (7) | C18—C23—C22 | 123.9 (7) |
C2—C7—H7A | 119.2 | C18—C23—H23A | 118.1 |
C6—C7—H7A | 119.2 | C22—C23—H23A | 118.1 |
C9—C8—H8A | 109.5 | C25—C24—H24A | 109.5 |
C9—C8—H8B | 109.5 | C25—C24—H24B | 109.5 |
H8A—C8—H8B | 109.5 | H24A—C24—H24B | 109.5 |
C9—C8—H8C | 109.5 | C25—C24—H24C | 109.5 |
H8A—C8—H8C | 109.5 | H24A—C24—H24C | 109.5 |
H8B—C8—H8C | 109.5 | H24B—C24—H24C | 109.5 |
C10—C9—C14 | 118.3 (6) | C26—C25—C30 | 117.7 (7) |
C10—C9—C8 | 119.6 (6) | C26—C25—C24 | 119.2 (7) |
C14—C9—C8 | 122.1 (6) | C30—C25—C24 | 123.1 (7) |
C11—C10—C9 | 120.9 (7) | C27—C26—C25 | 122.2 (6) |
C11—C10—H10A | 119.6 | C27—C26—H26A | 118.9 |
C9—C10—H10A | 119.6 | C25—C26—H26A | 118.9 |
C12—C11—C10 | 119.3 (8) | C26—C27—C28 | 117.6 (8) |
C12—C11—H11A | 120.4 | C26—C27—C31 | 122.1 (7) |
C10—C11—H11A | 120.4 | C28—C27—C31 | 120.0 (7) |
C11—C12—C13 | 122.8 (8) | C29—C28—C27 | 121.4 (8) |
C11—C12—O3 | 118.3 (7) | C29—C28—O5 | 117.7 (7) |
C13—C12—O3 | 118.6 (7) | C27—C28—O5 | 120.8 (7) |
C14—C13—C12 | 114.8 (7) | C30—C29—C28 | 119.3 (8) |
C14—C13—C15 | 123.3 (7) | C30—C29—H29A | 120.3 |
C12—C13—C15 | 121.8 (7) | C28—C29—H29A | 120.3 |
C9—C14—C13 | 123.8 (6) | C29—C30—C25 | 121.6 (8) |
C9—C14—H14A | 118.1 | C29—C30—H30A | 119.2 |
C13—C14—H14A | 118.1 | C25—C30—H30A | 119.2 |
C13—C15—C16 | 114.9 (6) | C22—C31—C27 | 109.3 (5) |
C13—C15—C4 | 108.5 (5) | C22—C31—C32 | 114.8 (6) |
C16—C15—C4 | 112.9 (6) | C27—C31—C32 | 113.1 (6) |
C13—C15—H15A | 106.7 | C22—C31—H31A | 106.4 |
C16—C15—H15A | 106.7 | C27—C31—H31A | 106.4 |
C4—C15—H15A | 106.7 | C32—C31—H31A | 106.4 |
C15—C16—H16A | 109.5 | C31—C32—H32A | 109.5 |
C15—C16—H16B | 109.5 | C31—C32—H32B | 109.5 |
H16A—C16—H16B | 109.5 | H32A—C32—H32B | 109.5 |
C15—C16—H16C | 109.5 | C31—C32—H32C | 109.5 |
H16A—C16—H16C | 109.5 | H32A—C32—H32C | 109.5 |
H16B—C16—H16C | 109.5 | H32B—C32—H32C | 109.5 |
O1—S1—O2—C5 | −29.3 (6) | O4—S2—O5—C28 | 28.1 (7) |
O3—S1—O2—C5 | 85.6 (6) | O6—S2—O5—C28 | −84.2 (6) |
O1—S1—O3—C12 | 27.4 (7) | O4—S2—O6—C21 | −31.6 (6) |
O2—S1—O3—C12 | −86.3 (6) | O5—S2—O6—C21 | 84.0 (5) |
C7—C2—C3—C4 | −2.7 (11) | C23—C18—C19—C20 | 4.6 (10) |
C1—C2—C3—C4 | 178.1 (7) | C17—C18—C19—C20 | −179.3 (7) |
C2—C3—C4—C5 | 3.1 (10) | C18—C19—C20—C21 | −5.6 (11) |
C2—C3—C4—C15 | 174.6 (6) | S2—O6—C21—C22 | −89.2 (8) |
C3—C4—C5—C6 | −2.9 (11) | S2—O6—C21—C20 | 96.0 (8) |
C15—C4—C5—C6 | −174.4 (7) | C19—C20—C21—O6 | 178.9 (7) |
C3—C4—C5—O2 | −179.2 (7) | C19—C20—C21—C22 | 4.0 (12) |
C15—C4—C5—O2 | 9.4 (10) | O6—C21—C22—C23 | −176.1 (7) |
S1—O2—C5—C6 | 93.5 (8) | C20—C21—C22—C23 | −1.4 (11) |
S1—O2—C5—C4 | −90.2 (7) | O6—C21—C22—C31 | 8.1 (11) |
C4—C5—C6—C7 | 2.4 (11) | C20—C21—C22—C31 | −177.2 (7) |
O2—C5—C6—C7 | 178.6 (6) | C19—C18—C23—C22 | −2.1 (11) |
C3—C2—C7—C6 | 2.0 (11) | C17—C18—C23—C22 | −178.2 (7) |
C1—C2—C7—C6 | −178.8 (7) | C21—C22—C23—C18 | 0.5 (11) |
C5—C6—C7—C2 | −1.9 (12) | C31—C22—C23—C18 | 176.2 (7) |
C14—C9—C10—C11 | −0.6 (10) | C30—C25—C26—C27 | 0.4 (10) |
C8—C9—C10—C11 | 177.9 (7) | C24—C25—C26—C27 | −178.5 (6) |
C9—C10—C11—C12 | 1.7 (10) | C25—C26—C27—C28 | −0.5 (10) |
C10—C11—C12—C13 | −0.9 (10) | C25—C26—C27—C31 | −175.5 (6) |
C10—C11—C12—O3 | −175.3 (6) | C26—C27—C28—C29 | −1.1 (10) |
S1—O3—C12—C11 | −96.8 (7) | C31—C27—C28—C29 | 174.0 (6) |
S1—O3—C12—C13 | 88.6 (7) | C26—C27—C28—O5 | 175.2 (6) |
C11—C12—C13—C14 | −1.0 (9) | C31—C27—C28—O5 | −9.6 (10) |
O3—C12—C13—C14 | 173.4 (5) | S2—O5—C28—C29 | −94.4 (7) |
C11—C12—C13—C15 | 178.1 (6) | S2—O5—C28—C27 | 89.1 (7) |
O3—C12—C13—C15 | −7.6 (9) | C27—C28—C29—C30 | 2.8 (10) |
C10—C9—C14—C13 | −1.5 (10) | O5—C28—C29—C30 | −173.7 (6) |
C8—C9—C14—C13 | −180.0 (6) | C28—C29—C30—C25 | −2.8 (10) |
C12—C13—C14—C9 | 2.2 (9) | C26—C25—C30—C29 | 1.3 (10) |
C15—C13—C14—C9 | −176.8 (6) | C24—C25—C30—C29 | −179.8 (7) |
C14—C13—C15—C16 | −32.3 (8) | C23—C22—C31—C27 | −88.7 (9) |
C12—C13—C15—C16 | 148.7 (6) | C21—C22—C31—C27 | 86.8 (8) |
C14—C13—C15—C4 | 95.1 (7) | C23—C22—C31—C32 | 39.5 (10) |
C12—C13—C15—C4 | −83.8 (8) | C21—C22—C31—C32 | −145.0 (6) |
C3—C4—C15—C13 | −85.1 (8) | C26—C27—C31—C22 | 90.0 (8) |
C5—C4—C15—C13 | 85.9 (8) | C28—C27—C31—C22 | −84.9 (8) |
C3—C4—C15—C16 | 43.4 (9) | C26—C27—C31—C32 | −39.2 (9) |
C5—C4—C15—C16 | −145.6 (6) | C28—C27—C31—C32 | 145.9 (6) |
Experimental details
Crystal data | |
Chemical formula | C16H16O3S |
Mr | 288.36 |
Crystal system, space group | Orthorhombic, Pca21 |
Temperature (K) | 298 |
a, b, c (Å) | 14.122 (3), 8.0880 (16), 25.343 (5) |
V (Å3) | 2894.6 (10) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.23 |
Crystal size (mm) | 0.30 × 0.20 × 0.10 |
Data collection | |
Diffractometer | Enraf–Nonius CAD-4 diffractometer |
Absorption correction | ψ scan (North et al., 1968) |
Tmin, Tmax | 0.915, 0.958 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3213, 2890, 1444 |
Rint | 0.021 |
(sin θ/λ)max (Å−1) | 0.616 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.054, 0.116, 1.00 |
No. of reflections | 2890 |
No. of parameters | 361 |
No. of restraints | 202 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.31, −0.14 |
Absolute structure | Flack (1983), 208 Friedel pairs |
Absolute structure parameter | −0.06 (17) |
Computer programs: CAD-4 Software (Enraf–Nonius, 1989), CAD-4 Software, XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2000), SHELXTL.
S1—O1 | 1.381 (5) | S2—O4 | 1.375 (5) |
S1—O3 | 1.599 (5) | S2—O5 | 1.626 (5) |
S1—O2 | 1.625 (6) | S2—O6 | 1.639 (6) |
O2—C5 | 1.414 (8) | O5—C28 | 1.410 (8) |
O3—C12 | 1.418 (9) | O6—C21 | 1.391 (8) |
O1—S1—O3 | 109.3 (3) | O4—S2—O5 | 110.7 (3) |
O1—S1—O2 | 107.7 (3) | O4—S2—O6 | 106.2 (3) |
O3—S1—O2 | 101.8 (3) | O5—S2—O6 | 101.0 (3) |
C5—O2—S1 | 118.4 (5) | C28—O5—S2 | 122.3 (4) |
C12—O3—S1 | 123.6 (4) | C21—O6—S2 | 120.8 (5) |
C6—C5—O2 | 119.6 (7) | O6—C21—C22 | 121.4 (6) |
C4—C5—O2 | 118.9 (6) | O6—C21—C20 | 118.4 (7) |
C11—C12—O3 | 118.3 (7) | C29—C28—O5 | 117.7 (7) |
C13—C12—O3 | 118.6 (7) | C27—C28—O5 | 120.8 (7) |
In a research for novel antioxidants, a series of medium-ring heterocycles derived from sterically hindered phenols has been prepared and investigated (Pastor et al., 1983). We herein report the crystal structure of the title compound, (I).
The asymmetric unit of (I) contains two independent molecules, essentially in the same geometry (Fig. 1). The bond lengths and angles (Table 1) are within normal ranges (Allen et al., 1987).
Rings A(C2—C7), B(C9—C14), D(C18—C23) and E(C25—C30) are, of course, planar and the dihedral angles between them are A/B = 79.06 (2)° and D/E=78.46 (2)°. Rings C (S1/O2/O3/C4/C5/C12/C13/C15) and F (S2/O5/O6/C21/C22/C27/C28/C31) are not planar, having total puckering amplitudes, QT, of 1.057 (3) and 1.037 (3) Å, respectively, and boat-chair conformations (Cremer & Pople, 1975).