PhI(OAc)2-mediated trifluoromethylthiolation/oxidative cyclization of ynamides
Su, Shixuan; Yan, Zhipeng; Ye, Xingyuan; Wang, Jingyang; Li, Yuan; He, Guangke; Organic & Biomolecular Chemistry 19 (2021) 8746–8753; doi:10.1039/D1OB01642C

data_7158318
_publ_section_title
;
 PhI(OAc)2-mediated trifluoromethylthiolation/oxidative cyclization of
 ynamides
;
_journal_issue                   40
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_page_first              8746
_journal_page_last               8753
_journal_paper_doi               10.1039/D1OB01642C
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C17 H11 Br F3 N O3 S'
_chemical_formula_sum            'C17 H11 Br F3 N O3 S'
_chemical_formula_weight         446.24
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-08-18
_audit_creation_method
;
Olex2 1.5
(compiled 2021.07.19 svn.r715e62df for OlexSys, GUI svn.r6383)
;
_audit_update_record
;
2021-08-19 deposited with the CCDC.	2021-09-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.222(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.868(5)
_cell_length_b                   12.831(4)
_cell_length_c                   7.106(3)
_cell_measurement_reflns_used    4025
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      27.375
_cell_measurement_theta_min      2.683
_cell_volume                     1717.6(10)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      193.00
_diffrn_measured_fraction_theta_full 0.961
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON 100'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0618
_diffrn_reflns_av_unetI/netI     0.0755
_diffrn_reflns_Laue_measured_fraction_full 0.961
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            9748
_diffrn_reflns_point_group_measured_fraction_full 0.961
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.663
_diffrn_reflns_theta_min         1.920
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.563
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6015
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1433 before and 0.0690 after correction.
The Ratio of minimum to maximum transmission is 0.8067.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.726
_exptl_crystal_description       block
_exptl_crystal_F_000             888
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.995
_refine_diff_density_min         -1.464
_refine_diff_density_rms         0.171
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3813
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0885
_refine_ls_R_factor_gt           0.0668
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1596P)^2^+3.4299P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2057
_refine_ls_wR_factor_ref         0.2603
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2896
_reflns_number_total             3813
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob01642c2.cif
_cod_data_source_block           a
_cod_depositor_comments          'Adding full bibliography for 7158318.cif.'
_cod_original_cell_volume        1717.5(10)
_cod_database_code               7158318
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.784
_shelx_estimated_absorpt_t_min   0.748
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Uiso/Uaniso restraints and constraints
C1 \\sim C2: within 2A with sigma of 0.005 and sigma for terminal atoms of 0.01
within 2A
3.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C13(H13), C14(H14), C15(H15), C16(H16),
 C17(H17)
;
_shelx_res_checksum              18009
_olex2_submission_special_instructions 'No special instructions were received'