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_4034222
_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      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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-09-17
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 117.756(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   9.9275(4)
_cell_length_b                   30.6826(8)
_cell_length_c                   10.2669(5)
_cell_measurement_reflns_used    2663
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.8530
_cell_measurement_theta_min      3.5540
_cell_volume                     2767.5(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details
;
  1 omega  -48.00   44.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -57.0000  -60.0000 92

  2 omega    0.00   91.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   57.0000   90.0000 91

  3 omega   -1.00   27.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   19.0000  -60.0000 28
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0260092000
_diffrn_orient_matrix_UB_12      0.0144991000
_diffrn_orient_matrix_UB_13      -0.0606914000
_diffrn_orient_matrix_UB_21      0.0544817000
_diffrn_orient_matrix_UB_22      0.0156625000
_diffrn_orient_matrix_UB_23      0.0446154000
_diffrn_orient_matrix_UB_31      0.0535419000
_diffrn_orient_matrix_UB_32      -0.0089003000
_diffrn_orient_matrix_UB_33      -0.0203066000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_unetI/netI     0.0501
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9893
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.48
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.259
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93380
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         5419
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0657
_refine_ls_R_factor_gt           0.0478
_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^)+(0.0284P)^2^+1.3368P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0979
_refine_ls_wR_factor_ref         0.1079
_reflns_number_gt                4200
_reflns_number_total             5419
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo9b00181_si_002.cif
_cod_data_source_block           qiuyf_0913
_cod_depositor_comments
;

2020-04-07
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_cell_volume        2767.47(19)
_cod_original_formula_moiety     '2(C16 H10 F3 N S)'
_cod_original_formula_sum        'C32 H20 F6 N2 S2'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     610.62
_cod_database_code               4034222
_reflns_odcompleteness_completeness 99.15
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C23(H23), C21(H21), C31(H31), C27(H27), C30(H30), C18(H18), C28(H28),
 C29(H29), C20(H20), C19(H19), C7(H7), C11(H11), C2(H2), C4(H4), C5(H5),
 C15(H15), C14(H14), C12(H12), C3(H3), C13(H13)
;
_olex2_date_sample_data_collection 2018-09-14
_olex2_submission_special_instructions 'No special instructions were received'