Electrochemically driven regioselective construction of 4-sulfenyl-isochromenones from <i>o</i>-alkynylbenzoates and diaryl disulfides.
Dapkekar, Anil Balajirao; Satyanarayana, Gedu; Organic & biomolecular chemistry 22 (2024) 7111–7116; doi:10.1039/d4ob01137f

data_7160092
_publ_section_title
;
 Electrochemically driven regioselective construction of
 4-sulfenyl-isochromenones from <i>o</i>-alkynylbenzoates and diaryl
 disulfides.
;
_journal_issue                   35
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7111
_journal_page_last               7116
_journal_paper_doi               10.1039/d4ob01137f
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C23 H18 O4 S'
_chemical_formula_sum            'C23 H18 O4 S'
_chemical_formula_weight         390.43
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-01-08
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2023.11.24 svn.r209d9fb2 for OlexSys, GUI svn.r6869)
;
_audit_update_record
;
2024-03-31 deposited with the CCDC.	2024-08-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.742(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.3863(19)
_cell_length_b                   18.506(3)
_cell_length_c                   12.780(2)
_cell_measurement_reflns_used    3715
_cell_measurement_temperature    149.00
_cell_measurement_theta_max      24.88
_cell_measurement_theta_min      2.58
_cell_volume                     1878.2(6)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      149.00
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-IV Photon II'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0981
_diffrn_reflns_av_unetI/netI     0.0593
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            22124
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.995
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_min         2.201
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.200
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5069
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1683 before and 0.0788 after correction.
The Ratio of minimum to maximum transmission is 0.6800.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'metallic light colourless'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.045
_exptl_crystal_size_mid          0.036
_exptl_crystal_size_min          0.012
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       0.0041(8)
_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   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         3304
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0659
_refine_ls_R_factor_gt           0.0421
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0348P)^2^+0.7827P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0895
_refine_ls_wR_factor_ref         0.1004
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2495
_reflns_number_total             3304
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01137f2.cif
_cod_data_source_block           mo_gs_ab_cho_0m
_cod_depositor_comments          'Adding full bibliography for 7160092.cif.'
_cod_original_cell_volume        1878.3(6)
_cod_database_code               7160092
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_max   0.998
_shelx_estimated_absorpt_t_min   0.991
_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:
 C3(H3), C4(H4), C9(H9), C10(H10), C13(H13), C14(H14), C15(H15), C16(H16),
 C19(H19), C20(H20), C21(H21), C22(H22)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C12(H12A,H12B,H12C)
;
_shelx_res_checksum              92255
_olex2_exptl_crystal_mounting_method 'Nylon loop used'
_olex2_submission_special_instructions 'No special instructions were received'