Base-promoted cascade 5-<i>exo-dig</i> annulation/carboxylation of <i>o</i>-(1-alkynyl)benzenesulfonamides with CO<sub>2</sub>: divergent synthesis of mono- or <i>gem</i>-dicarboxylic esters.
Yao, Yang; Bai, Junxue; Cheng, Peidong; Yang, Han; Sun, Jianwei; Sun, Song; Chemical communications (Cambridge, England) 60 (2024) 14850–14853; doi:10.1039/d4cc05239k

data_7133968
_publ_section_title
;
 Base-promoted cascade 5-<i>exo-dig</i> annulation/carboxylation of
 <i>o</i>-(1-alkynyl)benzenesulfonamides with CO<sub>2</sub>: divergent
 synthesis of mono- or <i>gem</i>-dicarboxylic esters.
;
_journal_issue                   99
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              14850
_journal_page_last               14853
_journal_paper_doi               10.1039/d4cc05239k
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C18 H17 N O4 S'
_chemical_formula_sum            'C18 H17 N O4 S'
_chemical_formula_weight         343.38
_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             2022-06-30
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2023-07-07 deposited with the CCDC.	2024-11-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.78(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.907(4)
_cell_length_b                   10.099(4)
_cell_length_c                   17.406(7)
_cell_measurement_reflns_used    1352
_cell_measurement_temperature    128.00
_cell_measurement_theta_max      55.67
_cell_measurement_theta_min      4.43
_cell_volume                     1683.9(12)
_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  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      128.00
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34138
_diffrn_reflns_av_R_equivalents  0.1688
_diffrn_reflns_av_unetI/netI     0.1287
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11571
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        52.968
_diffrn_reflns_theta_max         52.968
_diffrn_reflns_theta_min         4.442
_diffrn_source_current           3.57
_diffrn_source_power             0.2494002
_diffrn_source_voltage           69.86
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.239
_exptl_absorpt_correction_T_max  0.7519
_exptl_absorpt_correction_T_min  0.4919
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1531 before and 0.0922 after correction.
The Ratio of minimum to maximum transmission is 0.6542.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.379
_refine_diff_density_min         -0.459
_refine_diff_density_rms         0.101
_refine_ls_extinction_coef       0.039(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         2909
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.998
_refine_ls_R_factor_all          0.1198
_refine_ls_R_factor_gt           0.0818
_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^)+(0.1603P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2078
_refine_ls_wR_factor_ref         0.2496
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1852
_reflns_number_total             2909
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc05239k2.cif
_cod_data_source_block           ga220630a_0m
_cod_depositor_comments
'Adding full bibliography for 7133968--7133969.cif.'
_cod_original_cell_volume        1683.8(12)
_cod_database_code               7133968
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.790
_shelx_estimated_absorpt_t_min   0.708
_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:
 C00A(H00A), C00D(H00E), C00F(H00F), C00H(H00H), C00I(H00I), C00J(H00J),
 C00K(H00K), C00L(H00L)
2.b Idealised Me refined as rotating group:
 C00B(H00B,H00C,H00D), C00M(H00G,H00M,H00N), C00O(H00O,H00P,H00Q)
;
_shelx_res_checksum              18665
_shelx_hkl_checksum              70124
_olex2_submission_special_instructions 'No special instructions were received'