I<sub>2</sub>-Catalyzed sulfenylation of indoles and pyrroles using triethylammonium thiolates as sulfenylating agents.
Fan, Wei; Yang, Zhen; Jiang, Bo; Li, Guigen; Organic chemistry frontiers : an international journal of organic chemistry 4 (2017) 1091–1102; doi:10.1039/C6QO00851H

data_4036788
_publ_section_title
;
 I<sub>2</sub>-Catalyzed sulfenylation of indoles and pyrroles using
 triethylammonium thiolates as sulfenylating agents.
;
_journal_issue                   6
_journal_name_full
'Organic chemistry frontiers : an international journal of organic chemistry'
_journal_page_first              1091
_journal_page_last               1102
_journal_paper_doi               10.1039/C6QO00851H
_journal_volume                  4
_journal_year                    2017
_chemical_formula_sum            'C31.5 H24.5 Br N2.5 O3.5 S'
_chemical_formula_weight         606.00
_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_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2016-12-13 deposited with the CCDC.
2017-02-17 downloaded from the CCDC.
;
_cell_angle_alpha                82.403(2)
_cell_angle_beta                 75.7150(10)
_cell_angle_gamma                70.4870(10)
_cell_formula_units_Z            4
_cell_length_a                   12.3295(11)
_cell_length_b                   13.0067(12)
_cell_length_c                   18.5167(16)
_cell_measurement_reflns_used    1973
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.166
_cell_measurement_theta_min      2.744
_cell_volume                     2708.3(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1118
_diffrn_reflns_av_sigmaI/netI    0.2092
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            14016
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.32
_exptl_absorpt_coefficient_mu    1.635
_exptl_absorpt_correction_T_max  0.8803
_exptl_absorpt_correction_T_min  0.5984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.486
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1240
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.668
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_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    mixed
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_refine_ls_number_reflns         9430
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.103
_refine_ls_R_factor_all          0.2123
_refine_ls_R_factor_gt           0.0947
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0575P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2052
_refine_ls_wR_factor_ref         0.2263
_reflns_number_gt                3284
_reflns_number_total             9430
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6qo00851h2.cif
_cod_data_source_block           161010a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Triclinic' was changed to
'triclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 

2025-10-08
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C63 H49 Br2 N5 O7 S2'
_cod_original_formula_weight         1212.01
_cod_original_formula_units_Z            2
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4036788