Continuous-flow electrosynthesis of selenium-substituted iminoisobenzofuran via oxidative cyclization of olefinic amides and diselenides.
Bian, Mixue; Hua, Jiawei; Ma, Tao; Xu, Jia; Cai, Chen; Yang, Zhao; Liu, Chengkou; He, Wei; Fang, Zheng; Guo, Kai; Organic & biomolecular chemistry 19 (2021) 3207–3212; doi:10.1039/d1ob00236h

data_7157933
_publ_section_title
;
 Continuous-flow electrosynthesis of selenium-substituted
 iminoisobenzofuran via oxidative cyclization of olefinic amides and
 diselenides.
;
_journal_issue                   14
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3207
_journal_page_last               3212
_journal_paper_doi               10.1039/d1ob00236h
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C23 H21 N O3 S Se'
_chemical_formula_sum            'C23 H21 N O3 S Se'
_chemical_formula_weight         470.43
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-07-06
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-07-31 deposited with the CCDC.	2021-03-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.128(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.5825(11)
_cell_length_b                   11.7312(12)
_cell_length_c                   16.2936(16)
_cell_measurement_reflns_used    9939
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      54.911
_cell_measurement_theta_min      4.133
_cell_volume                     2078.7(4)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      173.01
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0571
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            21511
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.961
_diffrn_reflns_theta_min         4.132
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.416
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.4454
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1568 before and 0.0783 after correction. The Ratio of minimum to maximum transmission is 0.5932. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.503
_exptl_crystal_description       block
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.294
_refine_diff_density_min         -1.125
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3934
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0349
_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^)+(0.0484P)^2^+1.5490P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0924
_refine_ls_wR_factor_ref         0.0946
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3680
_reflns_number_total             3934
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob00236h2.cif
_cod_data_source_block           2007018687_0m
_cod_depositor_comments          'Adding full bibliography for 7157933.cif.'
_cod_database_code               7157933
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.794
_shelx_estimated_absorpt_t_min   0.670
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6(H6), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16),
 C18(H18), C19(H19), C21(H21), C22(H22)
2.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C23(H23A,H23B,H23C)
;
_shelx_res_checksum              89605
_olex2_submission_special_instructions 'No special instructions were received'