Synthesis of Selenochromenes via Dehydration of Arylalkynols Promoted by Iron(III) Chloride and Diorganyl Diselenides.
Casola, Kamila Kayser; Gomes, Matheus Rick; Back, Davi F.; Zeni, Gilson; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c00741

data_4038344
_publ_section_title
;
 Synthesis of Selenochromenes via Dehydration of Arylalkynols Promoted by
 Iron(III) Chloride and Diorganyl Diselenides.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00741
_journal_year                    2020
_chemical_formula_moiety         'C22 H16 Se2'
_chemical_formula_sum            'C22 H16 Se2'
_chemical_formula_weight         438.27
_chemical_melting_point          336
_chemical_name_common            'methylene phenyl phenylselanyl selenochromene'
_chemical_name_systematic
;
4-methylene-2-phenyl-3-(phenylselanyl)-4H-selenochromene
;
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   '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             2019-07-12T15:32:20-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                110.327(2)
_cell_angle_beta                 92.316(2)
_cell_angle_gamma                96.373(2)
_cell_formula_units_Z            2
_cell_length_a                   7.0078(4)
_cell_length_b                   9.6334(6)
_cell_length_c                   13.8589(8)
_cell_measurement_reflns_used    6728
_cell_measurement_temperature    127(2)
_cell_measurement_theta_max      27.566
_cell_measurement_theta_min      3.146
_cell_volume                     868.78(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'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXL-2008 (Sheldrick, 2008)'
_diffrn_ambient_temperature      127(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_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  0.025
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10067
_diffrn_reflns_theta_full        27.57
_diffrn_reflns_theta_max         27.57
_diffrn_reflns_theta_min         2.26
_diffrn_source                   'micro-focus tube'
_exptl_absorpt_coefficient_mu    4.255
_exptl_absorpt_correction_T_max  0.7007
_exptl_absorpt_correction_T_min  0.35622
_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    1.675
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.424
_refine_diff_density_min         -0.481
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       none
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3941
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0268
_refine_ls_R_factor_gt           0.0225
_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^)+(0.0190P)^2^+0.5502P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0535
_refine_ls_wR_factor_ref         0.0551
_reflns_number_gt                3546
_reflns_number_total             3941
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            jo0c00741_si_002.cif
_cod_data_source_block           test2_a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '336K' was changed to '336'
-- 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 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_sg_symbol_Hall     -P1
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4038344