Synthesis of 3-(Organochalcogen) Chalcogenazolo Indoles via Cascade Cyclization of N-Alkynylindoles.
Prochnow, Thaís; Maroneze, Adriano; Back, Davi Fernando; Zeni, Gilson; The Journal of organic chemistry 84 (2019) 2891–2900; doi:10.1021/acs.joc.9b00052

data_4033690
_publ_section_title
;
 Synthesis of 3-(Organochalcogen) Chalcogenazolo Indoles via Cascade
 Cyclization of N-Alkynylindoles.
;
_journal_issue                   5
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2891
_journal_page_last               2900
_journal_paper_doi               10.1021/acs.joc.9b00052
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C33 H24 Cl2 N2 O Se4'
_chemical_formula_sum            'C33 H24 Cl2 N2 O Se4'
_chemical_formula_weight         851.28
_chemical_melting_point          ?
_chemical_name_common            'bis phenyl selenazole indole diselene'
_chemical_name_systematic
;
        1,2-bis(2-phenyl-[1,3]selenazole[3,2-a]indole-3-il)diselene
;
_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             2018-04-03T11:10:26-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                79.994(6)
_cell_angle_beta                 81.269(6)
_cell_angle_gamma                78.371(5)
_cell_formula_units_Z            2
_cell_length_a                   10.3911(5)
_cell_length_b                   11.0643(9)
_cell_length_c                   14.6903(12)
_cell_measurement_reflns_used    9988
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      68.042
_cell_measurement_theta_min      3.084
_cell_volume                     1617.1(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'
_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  0.0342
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13304
_diffrn_reflns_theta_full        68.74
_diffrn_reflns_theta_max         68.74
_diffrn_reflns_theta_min         3.08
_diffrn_source                   'micro-focus tube'
_exptl_absorpt_coefficient_mu    7.187
_exptl_absorpt_correction_T_max  0.8641
_exptl_absorpt_correction_T_min  0.5673
_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            orange
_exptl_crystal_density_diffrn    1.748
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             828
_exptl_crystal_size_max          0.376
_exptl_crystal_size_mid          0.228
_exptl_crystal_size_min          0.201
_refine_diff_density_max         0.769
_refine_diff_density_min         -0.603
_refine_diff_density_rms         0.107
_refine_ls_extinction_coef       none
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         5304
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.261
_refine_ls_R_factor_all          0.045
_refine_ls_R_factor_gt           0.0437
_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^)+(0.0715P)^2^+2.6147P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.128
_refine_ls_wR_factor_ref         0.1291
_reflns_number_gt                4998
_reflns_number_total             5304
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            jo9b00052_si_002.cif
_cod_data_source_block           dfbgz0317sese2_0m
_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 
;
_cod_original_sg_symbol_Hall     -P1
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4033690