Metal-Free Aminothiation of Alkynes: Three-Component Tandem Annulation toward Indolizine Thiones from 2-Alkylpyridines, Ynals, and Elemental Sulfur.
Chen, Zhengwang; Liang, Pei; Xu, Fan; Deng, Zhen; Long, Lipeng; Luo, Guotian; Ye, Min; The Journal of organic chemistry 84 (2019) 12639–12647; doi:10.1021/acs.joc.9b01802

data_4033958
_publ_section_title
;
 Metal-Free Aminothiation of Alkynes: Three-Component Tandem Annulation
 toward Indolizine Thiones from 2-Alkylpyridines, Ynals, and Elemental
 Sulfur.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12639
_journal_page_last               12647
_journal_paper_doi               10.1021/acs.joc.9b01802
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C17 H9 F3 N2'
_chemical_formula_sum            'C17 H9 F3 N2'
_chemical_formula_weight         298.26
_chemical_melting_point          ?
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_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                79.853(5)
_cell_angle_beta                 80.198(5)
_cell_angle_gamma                71.077(5)
_cell_formula_units_Z            2
_cell_length_a                   7.431(5)
_cell_length_b                   8.205(5)
_cell_length_c                   12.763(5)
_cell_measurement_reflns_used    3383
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.3
_cell_measurement_theta_min      3.3
_cell_volume                     719.2(7)
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1999)'
_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, 1997a)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.857
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       '\w scan'
_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  0.0257
_diffrn_reflns_av_sigmaI/netI    0.0352
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9338
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.32
_diffrn_reflns_theta_min         3.29
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_correction_T_min  0.971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.126
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.030
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3383
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.137
_refine_ls_R_factor_all          0.1150
_refine_ls_R_factor_gt           0.0684
_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^)+(0.0563P)^2^+0.1255P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1484
_refine_ls_wR_factor_ref         0.1700
_reflns_number_gt                2124
_reflns_number_total             3383
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo9b01802_si_002.cif
_cod_data_source_block           aa
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value 'not measured' was changed
to '?' -- the value is undefined or not given.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_Hall     -P_1
_cod_database_code               4033958