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_7131741
_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_absolute_configuration unk
_chemical_formula_moiety         'C27 H21 N O2 S Se'
_chemical_formula_sum            'C27 H21 N O2 S Se'
_chemical_formula_weight         502.499
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_Int_Tables_number      19
_atom_sites_solution_primary     dual
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.9597(4)
_cell_length_b                   18.6637(15)
_cell_length_c                   20.6440(13)
_cell_measurement_reflns_used    346
_cell_measurement_temperature    299.00
_cell_measurement_theta_max      31.21
_cell_measurement_theta_min      2.71
_cell_volume                     2296.2(3)
_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  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'XT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      299.00
_diffrn_measured_fraction_theta_full 0.9992
_diffrn_measured_fraction_theta_max 0.9993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0579
_diffrn_reflns_av_unetI/netI     0.0543
_diffrn_reflns_Laue_measured_fraction_full 0.9992
_diffrn_reflns_Laue_measured_fraction_max 0.9993
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            19920
_diffrn_reflns_point_group_measured_fraction_full 0.9964
_diffrn_reflns_point_group_measured_fraction_max 0.9963
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         27.10
_diffrn_reflns_theta_min         2.18
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.751
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.5315
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1525 before and 0.0875 after correction.
The Ratio of minimum to maximum transmission is 0.7129.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.454
_exptl_crystal_description       block
_exptl_crystal_F_000             1024.979
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.234
_exptl_crystal_size_min          0.095
_refine_diff_density_max         0.3074
_refine_diff_density_min         -0.5272
_refine_diff_density_rms         0.0580
_refine_ls_abs_structure_details
'Hooft, R.W.W., Straver, L.H., Spek, A.L. (2010). J. Appl. Cryst., 43, 665-668.'
_refine_ls_abs_structure_Flack   0.078(8)
_refine_ls_d_res_high            0.7800
_refine_ls_d_res_low             9.3318
_refine_ls_goodness_of_fit_ref   1.0275
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    40
_refine_ls_number_parameters     290
_refine_ls_number_reflns         5060
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0275
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_gt           0.0351
_refine_ls_shift/su_max          -0.0018
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0359P)^2^+0.0434P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0808
_refine_ls_wR_factor_ref         0.0856
_reflns_Friedel_coverage         0.992
_reflns_limit_h_max              7
_reflns_limit_h_min              -7
_reflns_limit_k_max              23
_reflns_limit_k_min              -23
_reflns_limit_l_max              26
_reflns_limit_l_min              -26
_reflns_number_gt                4309
_reflns_number_total             5060
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d3cc02294c2.cif
_cod_data_source_block           mo_gs_ab_2_537_0m
_cod_original_sg_symbol_Hall     ' P 2ac 2ab'
_cod_database_code               7131741
_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.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C25(H25), C26(H26), C6(H6), C7(H7), C10(H10), C11(H11), C12(H12),
 C13(H13), C15(H15), C16(H16), C17(H17), C18(H18), C19(H19), C21(H21), C22(H22),
  C23(H23), C24(H24)
2.b Idealised Me refined as rotating group:
 C8(H8a,H8b,H8c)
;
_olex2_exptl_crystal_mounting_method 'Nylon loop'
_olex2_submission_special_instructions 'No special instructions were received'