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_7157479
_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_absolute_configuration rmad
_chemical_formula_moiety         'C22 H17 N O2 Se'
_chemical_formula_sum            'C22 H17 N O2 Se'
_chemical_formula_weight         406.32
_chemical_melting_point          ?
_chemical_name_common            'azaspiro deca trienedione'
_chemical_name_systematic
;
1-methyl-4-phenyl-3-(phenylselanyl)-1-azaspiro[4.5]deca-3,7,9-triene-2,6-dione
;
_space_group_IT_number           7
_space_group_name_Hall           'P -2yc'
_space_group_name_H-M_alt        'P 1 c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P -2yc'
_symmetry_space_group_name_H-M   'P 1 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             2019-06-14T17:16:50-00:00
_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                 98.129(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.6477(5)
_cell_length_b                   14.9116(8)
_cell_length_c                   13.3181(7)
_cell_measurement_reflns_used    9259
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      25.547
_cell_measurement_theta_min      2.532
_cell_volume                     1896.73(17)
_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, 2008)'
_computing_structure_solution    'SHELXL-2008 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(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  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0429
_diffrn_reflns_av_unetI/netI     0.0376
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            78808
_diffrn_reflns_theta_full        28.4
_diffrn_reflns_theta_max         28.4
_diffrn_reflns_theta_min         2.53
_diffrn_source                   'micro-focus tube'
_exptl_absorpt_coefficient_mu    1.995
_exptl_absorpt_correction_T_max  0.6811
_exptl_absorpt_correction_T_min  0.5201
_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            yellow
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.54
_refine_diff_density_min         -0.562
_refine_diff_density_rms         0.18
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.021(7)
_refine_ls_extinction_coef       none
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     469
_refine_ls_number_reflns         9479
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0377
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0699P)^2^+0.0316P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0994
_refine_ls_wR_factor_ref         0.1104
_reflns_number_gt                7599
_reflns_number_total             9479
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            d0ob00609b2.cif
_cod_data_source_block           teste2_a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value 'none' was changed to '?'
-- the value is undefined or not given.

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.

2024-12-16
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_sg_symbol_Hall     P-2yc
_cod_original_sg_symbol_H-M      P1c1
_cod_original_formula_moiety     'C44 H34 N2 O4 Se2'
_cod_original_formula_sum        'C44 H34 N2 O4 Se2'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     812.65
_cod_database_code               7157479