Electrophilic Cyclization Involving Carbon-Selenium/Carbon-Halide Bond Formation: Synthesis of 3-Substituted Selenophenes.
Casola, Kamila Kaiser; Gomes, Matheus Rick; Back, Davi Fernando; Zeni, Gilson; The Journal of organic chemistry 83 (2018) 6706–6718; doi:10.1021/acs.joc.8b01136

data_4035822
_publ_section_title
;
 Electrophilic Cyclization Involving Carbon-Selenium/Carbon-Halide Bond
 Formation: Synthesis of 3-Substituted Selenophenes.
;
_journal_issue                   12
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              6706
_journal_page_last               6718
_journal_paper_doi               10.1021/acs.joc.8b01136
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C14 H13 I Se'
_chemical_formula_sum            'C14 H13 I Se'
_chemical_formula_weight         387.1
_chemical_melting_point          ?
_chemical_name_common            'iodo phenyl tetrahydrobenzo selephene'
_chemical_name_systematic
;
        3-iodo-2-phenyl-4,5,6,7-tetrahydrobenzo[b]selephene
;
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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             2017-09-27T17:20:15-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 98.1430(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.4395(4)
_cell_length_b                   8.6100(4)
_cell_length_c                   16.0486(6)
_cell_measurement_reflns_used    9966
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      22.61
_cell_measurement_theta_min      2.503
_cell_volume                     1291.18(9)
_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, Bonn-Germany'
_computing_structure_refinement  'SHELXL-2008 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXL-2008 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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           AgK\a
_diffrn_radiation_wavelength     0.56086
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_unetI/netI     0.0176
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            21516
_diffrn_reflns_theta_full        22.61
_diffrn_reflns_theta_max         22.61
_diffrn_reflns_theta_min         2.02
_diffrn_source                   'micro-focus tube'
_exptl_absorpt_coefficient_mu    2.795
_exptl_absorpt_correction_T_max  0.6633
_exptl_absorpt_correction_T_min  0.4778
_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    1.991
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.626
_refine_diff_density_min         -0.578
_refine_diff_density_rms         0.141
_refine_ls_extinction_coef       none
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.212
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         3468
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.212
_refine_ls_R_factor_all          0.0224
_refine_ls_R_factor_gt           0.019
_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^)+(0.0000P)^2^+3.0075P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0408
_refine_ls_wR_factor_ref         0.0477
_reflns_number_gt                3201
_reflns_number_total             3468
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            jo8b01136_si_002.cif
_cod_data_source_block           test
_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 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_Hall     -P2yn
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               4035822