Selenium-promoted electrophilic cyclization of arylpropiolamides: synthesis of 3-organoselenyl spiro[4,5]trienones.
Recchi, Ana Maria S.; Rosa, Pedro H. P.; Back, Davi F.; Zeni, Gilson; Organic & biomolecular chemistry 18 (2020) 3544–3551; doi:10.1039/d0ob00609b

data_7157478
_publ_section_title
;
 Selenium-promoted electrophilic cyclization of arylpropiolamides:
 synthesis of 3-organoselenyl spiro[4,5]trienones.
;
_journal_issue                   18
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3544
_journal_page_last               3551
_journal_paper_doi               10.1039/d0ob00609b
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C23 H16 F3 N O2 Se'
_chemical_formula_sum            'C23 H16 F3 N O2 Se'
_chemical_formula_weight         474.33
_chemical_melting_point          421
_chemical_name_common            'phenylselanyl azaspiro decatrienedione'
_chemical_name_systematic
'1-methyl-4-phenyl-3-((3-(trifluoromethyl)phenyl)selanyl)-1-azaspiro        [4.5]deca-3,6,9-triene-2,8-dione'
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_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_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_date             2019-06-14T16:48:24-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2020-03-19 deposited with the CCDC.	2020-04-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.147(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.7568(4)
_cell_length_b                   25.3971(13)
_cell_length_c                   13.5914(8)
_cell_measurement_reflns_used    7325
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.774
_cell_measurement_theta_min      2.843
_cell_volume                     1967.1(2)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'Bruker Instrument Service v4.2.7'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'Diamond (version 3.2i; Crystal Impact GbR'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXL97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 Quest Photon 100 diffractometer'
_diffrn_measurement_method       '2\% \f & \w scans'
_diffrn_radiation_monochromator  'Montel type 2-dim beam shaping X ray optics'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_av_unetI/netI     0.0365
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            22029
_diffrn_reflns_theta_full        27.16
_diffrn_reflns_theta_max         27.16
_diffrn_reflns_theta_min         2.21
_diffrn_source                   'micro-focus tube'
_exptl_absorpt_coefficient_mu    1.957
_exptl_absorpt_correction_T_max  0.9358
_exptl_absorpt_correction_T_min  0.6504
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS (version 2012/1; Bruker, 2012) was used to perform the numerical
        absorption correction based on the indexed faces of the crystal.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.602
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tabular
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.482
_refine_diff_density_min         -0.429
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       none
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         4358
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0608
_refine_ls_R_factor_gt           0.041
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0441P)^2^+1.6050P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0915
_refine_ls_wR_factor_ref         0.0981
_reflns_number_gt                3415
_reflns_number_total             4358
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            d0ob00609b2.cif
_cod_data_source_block           test_a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '421K' was changed to '421'
-- the value should be numeric and without a unit designator.

data item '_exptl_crystal_density_meas' value 'none' was changed to
'?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7157478--7157479.cif.
;
_cod_original_sg_symbol_Hall     -P2ybc
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7157478