Silver-Mediated Oxidative Decarboxylative Trifluoromethylthiolation of Coumarin-3-carboxylic Acids.
Li, Minghao; Petersen, Jeffrey L.; Hoover, Jessica M.; Organic letters 19 (2017) 638–641; doi:10.1021/acs.orglett.6b03806

data_1545136
_publ_section_title
;
 Silver-Mediated Oxidative Decarboxylative Trifluoromethylthiolation of
 Coumarin-3-carboxylic Acids.
;
_journal_issue                   3
_journal_name_full               'Organic letters'
_journal_page_first              638
_journal_page_last               641
_journal_paper_doi               10.1021/acs.orglett.6b03806
_journal_volume                  19
_journal_year                    2017
_chemical_formula_sum            'C11 H6 Br F3 O3 S'
_chemical_formula_weight         355.13
_space_group_crystal_system      tetragonal
_space_group_IT_number           92
_space_group_name_Hall           'P 4abw 2nw'
_space_group_name_H-M_alt        'P 41 21 2'
_symmetry_space_group_name_Hall  'P 4abw 2nw'
_symmetry_space_group_name_H-M   'P 41 21 2'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.9189(5)
_cell_length_b                   13.9189(5)
_cell_length_c                   12.9169(5)
_cell_measurement_reflns_used    9873
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      32.5300
_cell_measurement_theta_min      3.1543
_cell_volume                     2502.47(16)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker AXS D8 Venture fixed chi'
_diffrn_measurement_method       'omega scan, PHOTON 100 CMOS'
_diffrn_radiation_monochromator  Triumph
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            26231
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         3.27
_diffrn_source_type              'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    3.489
_exptl_absorpt_correction_T_max  0.52
_exptl_absorpt_correction_T_min  0.33
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/3 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.885
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelopiped
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.517
_exptl_crystal_size_mid          0.258
_exptl_crystal_size_min          0.214
_refine_diff_density_max         0.826
_refine_diff_density_min         -0.301
_refine_ls_abs_structure_details
;
Flack x determined using 1341 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.025(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         3645
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0313
_refine_ls_R_factor_gt           0.0261
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0298P)^2^+0.5417P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0591
_refine_ls_wR_factor_ref         0.0609
_reflns_number_gt                3384
_reflns_number_total             3645
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b03806_si_002.cif
_cod_data_source_block           I
_cod_depositor_comments          'Adding full bibliography for 1545136.cif.'
_cod_original_cell_volume        2502.5(2)
_cod_database_code               1545136
_shelx_res_checksum              39393
_shelx_hkl_checksum              33210