AgSCF<sub>3</sub>/Na<sub>2</sub>S<sub>2</sub>O<sub>8</sub>-Promoted Trifluoromethylthiolation/Cyclization of o-Propargyl Arylazides/ o-Alkynyl Benzylazides: Synthesis of SCF<sub>3</sub>-Substituted Quinolines and Isoquinolines.
Qiu, Yi-Feng; Niu, Yue-Jie; Wei, Xi; Cao, Bao-Qian; Wang, Xi-Cun; Quan, Zheng-Jun; The Journal of organic chemistry 84 (2019) 4165–4178; doi:10.1021/acs.joc.9b00181

data_4034221
_publ_section_title
;
 AgSCF<sub>3</sub>/Na<sub>2</sub>S<sub>2</sub>O<sub>8</sub>-Promoted
 Trifluoromethylthiolation/Cyclization of o-Propargyl Arylazides/
 o-Alkynyl Benzylazides: Synthesis of SCF<sub>3</sub>-Substituted
 Quinolines and Isoquinolines.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4165
_journal_page_last               4178
_journal_paper_doi               10.1021/acs.joc.9b00181
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C16 H10 F3 N S'
_chemical_formula_sum            'C16 H10 F3 N S'
_chemical_formula_weight         305.31
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   5.56940(10)
_cell_length_b                   16.5355(4)
_cell_length_c                   30.0961(6)
_cell_measurement_reflns_used    9928
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      25.05
_cell_measurement_theta_min      2.55
_cell_volume                     2771.63(10)
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_diffrn_ambient_temperature      291(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0993
_diffrn_reflns_av_unetI/netI     0.0443
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            47182
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.164
_diffrn_reflns_theta_max         25.164
_diffrn_reflns_theta_min         2.375
_exptl_absorpt_coefficient_mu    0.259
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_description       block
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.250
_refine_diff_density_max         0.131
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 1295 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.010(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.954
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         4964
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.954
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0279
_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^)+(0.0310P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0606
_refine_ls_wR_factor_ref         0.0631
_reflns_Friedel_coverage         0.718
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                3729
_reflns_number_total             4964
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b00181_si_003.cif
_cod_data_source_block           yao
_cod_original_cell_volume        2771.64(10)
_cod_database_code               4034221
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.922
_shelx_estimated_absorpt_t_max   0.938
_shelx_res_checksum              10564
_shelx_hkl_checksum              96421