Synthesis of Substituted 4 H-Thiochromen-4-imines via Copper-Catalyzed Cyclization Cascades of o-Bromobenzothioamides with Terminal Alkynes.
Ma, Yong-Gang; Huang, Meng-Qiao; Liu, Zhenhua; Liu, Jian-Quan; Wang, Xiang-Shan; The Journal of organic chemistry 83 (2018) 9504–9509; doi:10.1021/acs.joc.8b01180

data_4035316
_publ_section_title
;
 Synthesis of Substituted 4 H-Thiochromen-4-imines via Copper-Catalyzed
 Cyclization Cascades of o-Bromobenzothioamides with Terminal Alkynes.
;
_journal_issue                   16
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9504
_journal_page_last               9509
_journal_paper_doi               10.1021/acs.joc.8b01180
_journal_volume                  83
_journal_year                    2018
_chemical_formula_sum            'C21 H15 N S'
_chemical_formula_weight         313.40
_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_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                109.823(4)
_cell_angle_beta                 98.135(4)
_cell_angle_gamma                104.068(4)
_cell_formula_units_Z            2
_cell_length_a                   6.1542(7)
_cell_length_b                   11.9256(12)
_cell_length_c                   12.3170(14)
_cell_measurement_reflns_used    1650
_cell_measurement_temperature    276(2)
_cell_measurement_theta_max      25.38
_cell_measurement_theta_min      3.10
_cell_volume                     799.68(16)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      276(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0964
_diffrn_reflns_av_sigmaI/netI    0.1015
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9086
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         3.10
_exptl_absorpt_coefficient_mu    0.201
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.123
_exptl_crystal_size_mid          0.102
_exptl_crystal_size_min          0.096
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2821
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.1483
_refine_ls_R_factor_gt           0.0685
_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^)+(0.0393P)^2^+0.1043P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1056
_refine_ls_wR_factor_ref         0.1258
_reflns_number_gt                1522
_reflns_number_total             2821
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8b01180_si_002.cif
_cod_data_source_block           3A
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Triclinic' was changed to
'triclinic' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_cell_volume        799.68(15)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4035316