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_1518129
_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            'C16 H20 O S'
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_symmetry_cell_setting           monoclinic
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_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 94.900(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.3276(9)
_cell_length_b                   13.983(2)
_cell_length_c                   19.681(3)
_cell_measurement_reflns_used    3217
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      26.44
_cell_measurement_theta_min      2.54
_cell_volume                     1460.8(4)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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
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_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       17
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_diffrn_reflns_limit_l_min       -25
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_diffrn_reflns_theta_full        26.99
_diffrn_reflns_theta_max         26.99
_diffrn_reflns_theta_min         1.79
_exptl_absorpt_coefficient_mu    0.208
_exptl_absorpt_correction_T_max  0.9030
_exptl_absorpt_correction_T_min  0.8510
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.184
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.80
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_exptl_crystal_size_min          0.50
_refine_diff_density_max         0.298
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_refine_ls_extinction_method     none
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_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         3180
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0630
_refine_ls_R_factor_gt           0.0541
_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^)+(0.0943P)^2^+0.1610P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1462
_refine_ls_wR_factor_ref         0.1553
_reflns_number_gt                2595
_reflns_number_total             3180
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5026102_si_006.cif
_cod_data_source_block           3ba
_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_sg_symbol_H-M      P2(1)/n
_cod_database_code               1518129