Palladium-Catalyzed ortho-Sulfonylation of 2-Aryloxypyridines and Subsequent Formation of ortho-Sulfonylated Phenols.
Xu, Yinfeng; Liu, Ping; Li, Shun-Li; Sun, Peipei; The Journal of organic chemistry 80 (2015) 1269–1274; doi:10.1021/jo5026095

data_4030397
_publ_section_title
;
 Palladium-Catalyzed ortho-Sulfonylation of 2-Aryloxypyridines and
 Subsequent Formation of ortho-Sulfonylated Phenols.
;
_journal_issue                   2
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1269
_journal_page_last               1274
_journal_paper_doi               10.1021/jo5026095
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety         'C22 H17 N O3 S'
_chemical_formula_sum            'C22 H17 N O3 S'
_chemical_formula_weight         375.43
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_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                82.958(3)
_cell_angle_beta                 78.274(3)
_cell_angle_gamma                87.522(4)
_cell_formula_units_Z            2
_cell_length_a                   8.799(2)
_cell_length_b                   9.982(3)
_cell_length_c                   10.691(3)
_cell_measurement_temperature    293(2)
_cell_volume                     912.3(4)
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL-PLUS (Sheldrick, 1990)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997'
_computing_structure_solution    'SHELXS-97(Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.884
_diffrn_measurement_device_type  'Bruker APEX CCD area-detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0188
_diffrn_reflns_av_sigmaI/netI    0.0350
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7567
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.38
_diffrn_reflns_theta_min         1.96
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_number         none
_exptl_absorpt_coefficient_mu    0.200
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_correction_T_min  0.970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.172
_exptl_crystal_size_mid          0.126
_exptl_crystal_size_min          0.113
_refine_diff_density_max         0.400
_refine_diff_density_min         -0.424
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         4052
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0709
_refine_ls_R_factor_gt           0.0496
_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^)+(0.0933P)^2^+0.1193P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1425
_refine_ls_wR_factor_ref         0.1601
_reflns_number_gt                3056
_reflns_number_total             4052
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5026095_si_002.cif
_cod_data_source_block           4
_cod_depositor_comments
'Adding full bibliography for 4030397--4030398.cif.'
_cod_database_code               4030397