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_4035821
_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         'C18 H15 Br Se'
_chemical_formula_sum            'C18 H15 Br Se'
_chemical_formula_weight         390.17
_chemical_melting_point          ?
_chemical_name_common            'bromo naphthalen tetrahydrobenzo selenophene'
_chemical_name_systematic
;
3-bromo-2-(naphthalen-2-yl)-4,5,6,7-tetrahydrobenzo[b]selenophene
;
_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             2018-04-12T14:24:13-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90.033(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   5.7033(2)
_cell_length_b                   22.7969(9)
_cell_length_c                   23.3729(9)
_cell_measurement_reflns_used    9612
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      74.528
_cell_measurement_theta_min      4.251
_cell_volume                     3038.9(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, Bonn-Germany'
_computing_structure_refinement  'SHELXL-2008 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXL-2008 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0469
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            65199
_diffrn_reflns_theta_full        74.62
_diffrn_reflns_theta_max         74.62
_diffrn_reflns_theta_min         2.71
_diffrn_source                   'micro-focus tube'
_exptl_absorpt_coefficient_mu    6.299
_exptl_absorpt_correction_T_max  0.8645
_exptl_absorpt_correction_T_min  0.5663
_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    1.706
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1536
_exptl_crystal_size_max          0.245
_exptl_crystal_size_mid          0.201
_exptl_crystal_size_min          0.194
_refine_diff_density_max         0.768
_refine_diff_density_min         -0.663
_refine_diff_density_rms         0.085
_refine_ls_extinction_coef       none
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         6186
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0364
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0518P)^2^+2.3671P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1023
_refine_ls_wR_factor_ref         0.1057
_reflns_number_gt                5630
_reflns_number_total             6186
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            jo8b01136_si_004.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 

2020-08-14
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_sg_symbol_Hall     -P2yn
_cod_original_sg_symbol_H-M      P21/n
_cod_original_formula_moiety     'C36 H30 Br2 Se2'
_cod_original_formula_sum        'C36 H30 Br2 Se2'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     780.34
_cod_database_code               4035821