An electrochemical cascade process: synthesis of 3-selenylindoles from 2-alkynylanilines with diselenides.
Dapkekar, Anil Balajirao; Satyanarayana, Gedu; Chemical communications (Cambridge, England)  (2023) –; doi:10.1039/d3cc02294c

data_7131740
_publ_section_title
;
 An electrochemical cascade process: synthesis of 3-selenylindoles from
 2-alkynylanilines with diselenides.
;
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_paper_doi               10.1039/d3cc02294c
_journal_year                    2023
_chemical_formula_moiety         'C28 H23 N O2 S Se'
_chemical_formula_sum            'C28 H23 N O2 S Se'
_chemical_formula_weight         516.49
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2023-05-11
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-05-11 deposited with the CCDC.	2023-06-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.163(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.9442(10)
_cell_length_b                   11.3228(10)
_cell_length_c                   10.8455(10)
_cell_measurement_reflns_used    8094
_cell_measurement_temperature    299.00
_cell_measurement_theta_max      26.31
_cell_measurement_theta_min      2.60
_cell_volume                     1220.3(2)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      299.00
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_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  0.0332
_diffrn_reflns_av_unetI/netI     0.0583
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12026
_diffrn_reflns_point_group_measured_fraction_full 0.960
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.103
_diffrn_reflns_theta_min         2.049
_exptl_absorpt_coefficient_mu    1.649
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.5797
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0965 before and 0.0766 after correction.
The Ratio of minimum to maximum transmission is 0.7776.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.123
_exptl_crystal_size_min          0.096
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 1794 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.042(6)
_refine_ls_extinction_coef       0.006(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     295
_refine_ls_number_reflns         5161
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0364
_refine_ls_R_factor_gt           0.0299
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0120P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0655
_refine_ls_wR_factor_ref         0.0698
_reflns_Friedel_coverage         0.829
_reflns_Friedel_fraction_full    0.918
_reflns_Friedel_fraction_max     0.915
_reflns_number_gt                4536
_reflns_number_total             5161
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc02294c2.cif
_cod_data_source_block           mo_gs_ab_2_560_0m
_cod_database_code               7131740
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_max   0.858
_shelx_estimated_absorpt_t_min   0.596
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C22) = Uanis(C27)
3.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C3(H3), C4(H4), C21(H21), C20(H20), C19(H19), C18(H18),
 C17(H17), C9(H9), C10(H10), C11(H11), C12(H12), C27(H27), C26(H26), C24(H24),
 C23(H23)
3.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C28(H28A,H28B,H28C)
;
_shelx_res_checksum              8580
_shelx_hkl_checksum              7128
_olex2_submission_special_instructions 'No special instructions were received'