Reverse selectivity in m-CPBA oxidation of oligothiophenes to sulfones.
Pappenfus, Ted M.; Melby, Jacob H.; Hansen, Brent B.; Sumption, Devin M.; Hubers, Scott A.; Janzen, Daron E.; Ewbank, Paul C.; McGee, Kari A.; Burand, Michael W.; Mann, Kent R.; Organic letters 9 (2007) 3721–3724; doi:10.1021/ol071369x

data_1505496
_publ_section_title
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 Reverse selectivity in m-CPBA oxidation of oligothiophenes to sulfones.
;
_journal_issue                   19
_journal_name_full               'Organic letters'
_journal_page_first              3721
_journal_page_last               3724
_journal_paper_doi               10.1021/ol071369x
_journal_volume                  9
_journal_year                    2007
_chemical_formula_moiety         'C22 H28 O2 S3'
_chemical_formula_sum            'C22 H28 O2 S3'
_chemical_formula_weight         420.62
_chemical_name_common            'Me2 3T O2'
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                84.673(3)
_cell_angle_beta                 84.832(3)
_cell_angle_gamma                83.554(3)
_cell_formula_units_Z            4
_cell_length_a                   8.7636(15)
_cell_length_b                   11.4311(19)
_cell_length_c                   22.392(4)
_cell_measurement_reflns_used    2725
_cell_measurement_temperature    173(2)
_cell_volume                     2212.2(7)
_computing_cell_refinement       'SAINT, Bruker'
_computing_data_collection       'SMART, Bruker'
_computing_data_reduction        'SAINT, Bruker'
_computing_molecular_graphics    'SHELXTL, Bruker'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Siemens SMART Platform CCD'
_diffrn_measurement_method       'area detector, omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_sigmaI/netI    0.0496
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            21450
_diffrn_reflns_theta_full        25.04
_diffrn_reflns_theta_max         25.04
_diffrn_reflns_theta_min         1.80
_exptl_absorpt_coefficient_mu    0.349
_exptl_absorpt_correction_T_max  0.970000
_exptl_absorpt_correction_T_min  0.886511
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, R. Blessing, 1995'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.425
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.378
_refine_diff_density_min         -0.386
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     523
_refine_ls_number_reflns         7780
_refine_ls_number_restraints     157
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0829
_refine_ls_R_factor_gt           0.0509
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0638P)^2^+0.3637P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1152
_refine_ls_wR_factor_ref         0.1250
_reflns_number_gt                5428
_reflns_number_total             7780
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol071369x-file001.cif
_cod_data_source_block           trimer
_cod_original_cell_volume        2212.2(6)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1505496