K2S2O8-mediated radical cyclisation of 2-alkynylthioanisoles or -selenoanisoles: a green and regioselective route to 3-nitrobenzothiophenes and benzoselenophenes
Lu, Shi-Chao; Wu, Botao; Zhang, Shi-Peng; Gong, Ya-Ling; Xu, Shu; RSC Advances 10 (2020) 19083–19087; doi:10.1039/D0RA03894F

data_7240560
_publ_section_title
;
 K2S2O8-mediated radical cyclisation of 2-alkynylthioanisoles or
 -selenoanisoles: a green and regioselective route to
 3-nitrobenzothiophenes and benzoselenophenes
;
_journal_issue                   32
_journal_name_full               'RSC Advances'
_journal_page_first              19083
_journal_page_last               19087
_journal_paper_doi               10.1039/D0RA03894F
_journal_volume                  10
_journal_year                    2020
_chemical_formula_moiety         'C14 H9 N O2 S'
_chemical_formula_sum            'C14 H9 N O2 S'
_chemical_formula_weight         255.28
_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             2019-01-18
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-05-07 deposited with the CCDC.	2020-05-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.5030(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.2070(2)
_cell_length_b                   17.4113(6)
_cell_length_c                   10.8693(4)
_cell_measurement_reflns_used    9722
_cell_measurement_temperature    178(2)
_cell_measurement_theta_max      55.05
_cell_measurement_theta_min      4.215
_cell_volume                     1158.55(7)
_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      178.27
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.981
_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  0.0600
_diffrn_reflns_av_unetI/netI     0.0444
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10969
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         55.022
_diffrn_reflns_theta_min         4.213
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.590
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5225
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1821 before and 0.0937 after correction. The Ratio of minimum to maximum transmission is 0.6959. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.491
_refine_diff_density_min         -0.729
_refine_diff_density_rms         0.090
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2175
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0558
_refine_ls_R_factor_gt           0.0543
_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^)+(0.1009P)^2^+0.3463P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1424
_refine_ls_wR_factor_ref         0.1441
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2060
_reflns_number_total             2175
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ra03894f2.cif
_cod_data_source_block           1901162580_0m
_cod_depositor_comments          'Adding full bibliography for 7240560.cif.'
_cod_database_code               7240560
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.925
_shelx_estimated_absorpt_t_min   0.857
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C12(H12), C13(H13),
 C14(H14)
;
_shelx_res_checksum              92328
_olex2_submission_special_instructions 'No special instructions were received'