Visible-light-induced metal and reagent-free oxidative coupling of sp2 C–H bonds with organo-dichalcogenides: synthesis of 3-organochalcogenyl indoles
Rathore, Vandana; Kumar, Sangit; Green Chemistry 21 (2019) 2670–; doi:10.1039/C9GC00007K

data_7232541
_publ_section_title
;
 Visible-light-induced metal and reagent-free oxidative coupling of sp2
 C--H bonds with organo-dichalcogenides: synthesis of 3-organochalcogenyl
 indoles
;
_journal_issue                   10
_journal_name_full               'Green Chemistry'
_journal_page_first              2670
_journal_paper_doi               10.1039/C9GC00007K
_journal_volume                  21
_journal_year                    2019
_chemical_formula_moiety         'C15 H12 Br N Se'
_chemical_formula_sum            'C15 H12 Br N Se'
_chemical_formula_weight         365.13
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-12-30 deposited with the CCDC.    2019-03-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.553(18)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.469(4)
_cell_length_b                   6.265(2)
_cell_length_c                   17.738(6)
_cell_measurement_reflns_used    6300
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      27.18
_cell_measurement_theta_min      2.31
_cell_volume                     1376.6(8)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0883
_diffrn_reflns_av_unetI/netI     0.0542
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            23179
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.832
_diffrn_reflns_theta_min         2.311
_exptl_absorpt_coefficient_mu    5.611
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.762
_exptl_crystal_description       plate
_exptl_crystal_F_000             712
_exptl_crystal_size_max          .15
_exptl_crystal_size_mid          .10
_exptl_crystal_size_min          .09
_refine_diff_density_max         1.433
_refine_diff_density_min         -1.278
_refine_diff_density_rms         0.111
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         3581
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0825
_refine_ls_R_factor_gt           0.0487
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0450P)^2^+2.5698P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1036
_refine_ls_wR_factor_ref         0.1188
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2480
_reflns_number_total             3581
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9gc00007k2.cif
_cod_data_source_block           F2_a
_cod_depositor_comments          'Adding full bibliography for 7232541.cif.'
_cod_database_code               7232541
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              46968