Twisting and turning the sulfonamide bond: synthetic, quantum chemical and crystallographic study.
Blahun, Oleksandr P.; Rozhenko, Alexander B.; Rusanov, Eduard; Zhersh, Serhii; Tolmachev, Andrey A.; Volochnyuk, Dmitriy M.; Grygorenko, Oleksandr O.; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.9b03394

data_4038102
_publ_section_title
;
 Twisting and turning the sulfonamide bond: synthetic, quantum chemical
 and crystallographic study.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b03394
_journal_year                    2020
_chemical_formula_moiety         'C6 H11 N O2 S'
_chemical_formula_sum            'C6 H11 N O2 S'
_chemical_formula_weight         161.22
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2016/4
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.6488(3)
_cell_length_b                   9.8314(5)
_cell_length_c                   11.5610(6)
_cell_measurement_reflns_used    1308
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.33
_cell_measurement_theta_min      3.52
_cell_volume                     755.71(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0592
_diffrn_reflns_av_unetI/netI     0.0543
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6415
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.373
_diffrn_reflns_theta_min         2.720
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.367
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6512
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_description       plate
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.5(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.923
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     130
_refine_ls_number_reflns         1547
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      0.925
_refine_ls_R_factor_all          0.0803
_refine_ls_R_factor_gt           0.0451
_refine_ls_shift/su_max          0.033
_refine_ls_shift/su_mean         0.007
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0462P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0890
_refine_ls_wR_factor_ref         0.1014
_reflns_Friedel_coverage         0.677
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                962
_reflns_number_total             1547
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b03394_si_007.cif
_cod_data_source_block           xray169full
_cod_database_code               4038102
_shelx_shelxl_version_number     2016/4
_shelx_estimated_absorpt_t_min   0.838
_shelx_estimated_absorpt_t_max   0.975
_shelx_res_checksum              45079
_shelx_hkl_checksum              6692