Nickel-catalyzed reaction of thioisatins and alkynes: a facile synthesis of thiochromones.
Inami, Tasuku; Kurahashi, Takuya; Matsubara, Seijiro; Organic letters 16 (2014) 5660–5662; doi:10.1021/ol5026102

data_1518127
_publ_section_title
;
 Nickel-catalyzed reaction of thioisatins and alkynes: a facile synthesis
 of thiochromones.
;
_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              5660
_journal_page_last               5662
_journal_paper_doi               10.1021/ol5026102
_journal_volume                  16
_journal_year                    2014
_chemical_formula_sum            'C23 H15 F3 O2 S'
_chemical_formula_weight         412.41
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.569(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.591(2)
_cell_length_b                   16.262(6)
_cell_length_c                   21.370(8)
_cell_measurement_reflns_used    1077
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      19.11
_cell_measurement_theta_min      2.50
_cell_volume                     1942.2(12)
_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      273(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_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  0.0565
_diffrn_reflns_av_sigmaI/netI    0.0826
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            11432
_diffrn_reflns_theta_full        27.10
_diffrn_reflns_theta_max         27.10
_diffrn_reflns_theta_min         1.57
_exptl_absorpt_coefficient_mu    0.211
_exptl_absorpt_correction_T_max  0.9895
_exptl_absorpt_correction_T_min  0.9590
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.625
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         4225
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.985
_refine_ls_R_factor_all          0.1576
_refine_ls_R_factor_gt           0.0799
_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^)+(0.1193P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1923
_refine_ls_wR_factor_ref         0.2336
_reflns_number_gt                2105
_reflns_number_total             4225
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5026102_si_004.cif
_cod_data_source_block           3am
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/home/saulius/struct/COD-crude-data--automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2827 2014-09-09 07:05:25Z andrius 

 Adding full bibliography for 1518126--1518130.cif.
;
_cod_original_cell_volume        1942.4(13)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1518127