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_7133969
_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         'C14 H15 N O6 S'
_chemical_formula_sum            'C14 H15 N O6 S'
_chemical_formula_weight         325.33
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-09-20
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2024-04-13 deposited with the CCDC.	2024-11-07 downloaded from the CCDC.
;
_cell_angle_alpha                74.518(2)
_cell_angle_beta                 88.476(3)
_cell_angle_gamma                84.620(2)
_cell_formula_units_Z            2
_cell_length_a                   7.9471(6)
_cell_length_b                   7.9767(6)
_cell_length_c                   12.2761(10)
_cell_measurement_reflns_used    6916
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      27.45
_cell_measurement_theta_min      2.57
_cell_volume                     746.66(10)
_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      150.00
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0634
_diffrn_reflns_av_unetI/netI     0.0514
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14032
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.554
_diffrn_reflns_theta_min         2.574
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.246
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5337
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1334 before and 0.0828 after correction.
The Ratio of minimum to maximum transmission is 0.7158.
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    1.447
_exptl_crystal_description       block
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.449
_refine_diff_density_min         -0.613
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         3395
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0733
_refine_ls_R_factor_gt           0.0539
_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^)+(0.0366P)^2^+1.1225P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1171
_refine_ls_wR_factor_ref         0.1375
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2767
_reflns_number_total             3395
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc05239k2.cif
_cod_data_source_block           mo_b230920a_0m
_cod_depositor_comments
'Adding full bibliography for 7133968--7133969.cif.'
_cod_database_code               7133969
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.953
_shelx_estimated_absorpt_t_min   0.930
_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:
 C00D(H00D), C00J(H00J), C00K(H00K)
2.b Idealised Me refined as rotating group:
 C00H(H00A,H00B,H00C), C00I(H00E,H00F,H00G), C00L(H00H,H00I,H00L), C00M(H00M,
 H00N,H00O)
;
_shelx_res_checksum              38610
_shelx_hkl_checksum              30501
_olex2_submission_special_instructions 'No special instructions were received'