Iodine-mediated regioselective 5-endo-dig electrophilic cyclization reaction of selenoenynes: synthesis of selenophene derivatives
Pistoia, Renan P.; Roehrs, Juliano A.; Back, Davi F.; Zeni, Gilson; Organic Chemistry Frontiers 4 (2017) 277–; doi:10.1039/C6QO00491A

data_1553554
_publ_section_title
;
 Iodine-mediated regioselective 5-endo-dig electrophilic cyclization
 reaction of selenoenynes: synthesis of selenophene derivatives
;
_journal_issue                   2
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              277
_journal_paper_doi               10.1039/C6QO00491A
_journal_volume                  4
_journal_year                    2017
_chemical_formula_moiety         'C18 H15 I O Se'
_chemical_formula_sum            'C18 H15 I O Se'
_chemical_formula_weight         453.16
_chemical_melting_point          357,4
_chemical_name_common            'iodo methoxy phenyl methyl phenylselenophene'
_chemical_name_systematic
;
3-iodo-5-(methoxy(phenyl)methyl)-2-phenylselenophene
;
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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      2.4
_audit_creation_date             2016-08-24T15:26:17-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2016-08-24 deposited with the CCDC.
2016-11-29 downloaded from the CCDC.
;
_cell_angle_alpha                90.000(2)
_cell_angle_beta                 94.075(3)
_cell_angle_gamma                90.0000(10)
_cell_formula_units_Z            8
_cell_length_a                   20.300(5)
_cell_length_b                   5.882(5)
_cell_length_c                   27.651(5)
_cell_measurement_reflns_used    8752
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.968
_cell_measurement_theta_min      2.409
_cell_volume                     3293(3)
_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, 2008)'
_computing_structure_solution    'SHELXL97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Venture 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  0.0546
_diffrn_reflns_av_unetI/netI     0.0691
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            17766
_diffrn_reflns_theta_full        30.09
_diffrn_reflns_theta_max         30.09
_diffrn_reflns_theta_min         2.41
_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    4.151
_exptl_absorpt_correction_T_max  0.8622
_exptl_absorpt_correction_T_min  0.6266
_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    1.828
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1744
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: MeOH/CH2Cl2'
_exptl_crystal_size_max          0.272
_exptl_crystal_size_mid          0.194
_exptl_crystal_size_min          0.078
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.414
_refine_diff_density_rms         0.153
_refine_ls_extinction_coef       none
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         4829
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0854
_refine_ls_R_factor_gt           0.046
_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^)+(0.0169P)^2^+13.3815P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0627
_refine_ls_wR_factor_ref         0.0699
_reflns_number_gt                3406
_reflns_number_total             4829
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            c6qo00491a2.cif
_cod_data_source_block           mo_dfbgz0716_0m
_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     -C2yc
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               1553554