Diorganyl Dichalcogenides-Promoted Nucleophilic Closure of 1,4-Diyn-3-ols: Synthesis of 2-Benzoyl Chalcogenophenes.
Roehrs, Juliano A.; Pistoia, Renan P.; Back, Davi F.; Zeni, Gilson; The Journal of organic chemistry 80 (2015) 12470–12481; doi:10.1021/acs.joc.5b02334

data_4036510
_publ_section_title
;
 Diorganyl Dichalcogenides-Promoted Nucleophilic Closure of
 1,4-Diyn-3-ols: Synthesis of 2-Benzoyl Chalcogenophenes.
;
_journal_issue                   24
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12470
_journal_page_last               12481
_journal_paper_doi               10.1021/acs.joc.5b02334
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety         'C20 H17 I O4 Se'
_chemical_formula_sum            'C20 H17 I O4 Se'
_chemical_formula_weight         527.2
_chemical_name_common
4-iodo-5-phenyl-2-(3,4,5-trimethoxybenzoyl)selenophene
_chemical_name_systematic
;
(4-iodo-5-phenylselenophene-2yl)(3,4,5-trimethoxybenzoyl)methanone
;
_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      2.3
_audit_creation_date             2013-12-02T16:08:01-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 93.011(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.3426(3)
_cell_length_b                   7.7556(3)
_cell_length_c                   30.4400(10)
_cell_measurement_reflns_used    9905
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.555
_cell_measurement_theta_min      2.444
_cell_volume                     1966.81(12)
_computing_cell_refinement       'BRUKER SANT'
_computing_data_collection       'BRUKER APEX-II'
_computing_data_reduction        'BRUKER SOFTWARE'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2000)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXL97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean none
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device_type  'X8 APEX II'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            27607
_diffrn_reflns_theta_full        27.27
_diffrn_reflns_theta_max         27.27
_diffrn_reflns_theta_min         1.34
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_number         none
_exptl_absorpt_coefficient_mu    3.5
_exptl_absorpt_correction_T_max  0.659
_exptl_absorpt_correction_T_min  0.196
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   XPREP
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.78
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.506
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.987
_refine_diff_density_min         -0.612
_refine_diff_density_rms         0.159
_refine_ls_extinction_coef       none
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.218
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         4262
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.218
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0401
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0514P)^2^+2.5524P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.104
_refine_ls_wR_factor_ref         0.1185
_reflns_number_gt                3638
_reflns_number_total             4262
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5b02334_si_002.cif
_cod_data_source_block           teste
_cod_depositor_comments
;
The following automatic conversions were performed:

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 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_Hall     -P2ybc
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               4036510