SeCl<sub>2</sub>-Mediated Approach Toward Indole-Containing Polysubstituted Selenophenes.
Martins, Guilherme M.; Back, Davi F.; Kaufman, Teodoro S.; Silveira, Claudio C.; The Journal of organic chemistry 83 (2018) 3252–3264; doi:10.1021/acs.joc.8b00166

data_4035164
_publ_section_title
;
 SeCl<sub>2</sub>-Mediated Approach Toward Indole-Containing
 Polysubstituted Selenophenes.
;
_journal_issue                   6
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3252
_journal_page_last               3264
_journal_paper_doi               10.1021/acs.joc.8b00166
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C23 H16 O Se2'
_chemical_formula_sum            'C23 H16 O Se2'
_chemical_formula_weight         466.28
_chemical_melting_point          467
_chemical_name_common
'methoxyphenyl phenylbenzo selenopheno selenophene'
_chemical_name_systematic
;
3-(4-methoxyphenyl)-2-phenylbenzo[b]selenopheno[3,2-d]selenophene
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -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             2016-09-01T15:53:20-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                94.317(16)
_cell_angle_beta                 115.917(16)
_cell_angle_gamma                115.692(14)
_cell_formula_units_Z            2
_cell_length_a                   10.260(2)
_cell_length_b                   10.6085(15)
_cell_length_c                   11.2369(17)
_cell_measurement_reflns_used    9947
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      74.985
_cell_measurement_theta_min      4.631
_cell_volume                     936.9(4)
_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 G'
_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           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.025
_diffrn_reflns_av_unetI/netI     0.018
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            21709
_diffrn_reflns_theta_full        74.79
_diffrn_reflns_theta_max         74.79
_diffrn_reflns_theta_min         4.63
_diffrn_source                   'micro-focus tube'
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_number         none
_exptl_absorpt_coefficient_mu    4.991
_exptl_absorpt_correction_T_max  0.3159
_exptl_absorpt_correction_T_min  0.2228
_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    1.653
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             460
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.337
_refine_diff_density_min         -0.414
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       none
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3826
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.119
_refine_ls_R_factor_all          0.0292
_refine_ls_R_factor_gt           0.029
_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^)+(0.0339P)^2^+0.5676P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0738
_refine_ls_wR_factor_ref         0.0739
_reflns_number_gt                3664
_reflns_number_total             3826
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            jo8b00166_si_003.cif
_cod_data_source_block           test4
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '467K' was changed to '467'
-- 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 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_cell_volume        936.9(3)
_cod_original_sg_symbol_Hall     -P1
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4035164