Electrochemical cascade migratory <i>versus ortho</i>-cyclization of 2-alkynylbenzenesulfonamides.
Shi, Zhaojiang; Dong, Shicheng; Liu, Ting; Wang, Wei-Zhen; Li, Nan; Yuan, Yaofeng; Zhu, Jun; Ye, Ke-Yin; Chemical science 15 (2024) 2827–2832; doi:10.1039/d3sc05229j

data_1570767
_publ_section_title
;
 Electrochemical cascade migratory <i>versus ortho</i>-cyclization of
 2-alkynylbenzenesulfonamides.
;
_journal_issue                   8
_journal_name_full               'Chemical science'
_journal_page_first              2827
_journal_page_last               2832
_journal_paper_doi               10.1039/d3sc05229j
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C21 H13 N O4 S'
_chemical_formula_sum            'C21 H13 N O4 S'
_chemical_formula_weight         375.38
_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             2022-06-25
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_audit_update_record
;
2023-06-24 deposited with the CCDC.	2024-01-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.504(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.086(3)
_cell_length_b                   5.5939(14)
_cell_length_c                   38.073(11)
_cell_measurement_reflns_used    4519
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      22.578
_cell_measurement_theta_min      2.542
_cell_volume                     1716.8(9)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1153
_diffrn_reflns_av_unetI/netI     0.0787
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_number            31689
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.206
_diffrn_reflns_theta_max         25.206
_diffrn_reflns_theta_min         2.146
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.217
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.4477
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1682 before and 0.0804 after correction.
The Ratio of minimum to maximum transmission is 0.6008.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_description       needle
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3082
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.1055
_refine_ls_R_factor_gt           0.0513
_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^)+(0.0459P)^2^+0.3529P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1048
_refine_ls_wR_factor_ref         0.1233
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1875
_reflns_number_total             3082
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc05229j2.cif
_cod_data_source_block           szj-078x
_cod_depositor_comments
'Adding full bibliography for 1570763--1570767.cif.'
_cod_original_cell_volume        1716.7(9)
_cod_database_code               1570767
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.979
_shelx_estimated_absorpt_t_min   0.979
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C008(H008), C00B(H00B), C00C(H00C), C00G(H00G), C00H(H00H), C00J(H00J),
 C00K(H00K), C00L(H00L), C00N(H00N), C00O(H00O), C00P(H00P), C00Q(H00Q),
 C00R(H00R)
;
_shelx_res_checksum              13119
_olex2_submission_special_instructions 'No special instructions were received'