Enantioselective synthesis of C3-functionalized 2,1-benzothiazine 2,2-dioxides by N-heterocyclic carbene catalysis.
Mroczyńska, Karina; Dobrzańska, Liliana; Rafiński, Zbigniew; Chemical communications (Cambridge, England) 60 (2024) 7176–7179; doi:10.1039/d4cc01754d

data_7133220
_publ_section_title
;
 Enantioselective synthesis of C3-functionalized 2,1-benzothiazine
 2,2-dioxides by N-heterocyclic carbene catalysis.
;
_journal_issue                   56
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              7176
_journal_page_last               7179
_journal_paper_doi               10.1039/d4cc01754d
_journal_volume                  60
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C27 H38 N2 O5 S Si'
_chemical_formula_sum            'C27 H38 N2 O5 S Si'
_chemical_formula_weight         530.74
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2024-03-14 deposited with the CCDC.	2024-06-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.349(1)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.9560(1)
_cell_length_b                   12.4093(1)
_cell_length_c                   12.9018(1)
_cell_measurement_reflns_used    31738
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      77.9750
_cell_measurement_theta_min      3.4370
_cell_volume                     1427.63(2)
_computing_cell_refinement       'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXL-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_av_unetI/netI     0.0198
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            42196
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.993
_diffrn_reflns_theta_min         3.441
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    1.717
_exptl_absorpt_correction_T_max  1.284
_exptl_absorpt_correction_T_min  0.768
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.89a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_description       plate
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 2660 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.007(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     334
_refine_ls_number_reflns         5911
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0262
_refine_ls_R_factor_gt           0.0260
_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^)+(0.0373P)^2^+0.3770P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0690
_refine_ls_wR_factor_ref         0.0692
_reflns_Friedel_coverage         0.852
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.923
_reflns_number_gt                5848
_reflns_number_total             5911
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc01754d2.cif
_cod_data_source_block           LD
_cod_depositor_comments          'Adding full bibliography for 7133220.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7133220
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.704
_shelx_estimated_absorpt_t_max   0.904
_shelx_res_checksum              49750
_shelx_hkl_checksum              45399