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_4038104
_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         'C5 H9 N O2 S'
_chemical_formula_sum            'C5 H9 N O2 S'
_chemical_formula_weight         147.19
_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
_audit_creation_method           SHELXL-2016/4
_cell_angle_alpha                90
_cell_angle_beta                 98.817(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.0536(3)
_cell_length_b                   6.8910(3)
_cell_length_c                   11.5341(4)
_cell_measurement_reflns_used    1218
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      24.87
_cell_measurement_theta_min      2.56
_cell_volume                     632.55(4)
_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      123(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_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  0.0386
_diffrn_reflns_av_unetI/netI     0.0384
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5650
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.385
_diffrn_reflns_theta_min         2.559
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.430
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6664
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.546
_exptl_crystal_description       plate
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.377
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     82
_refine_ls_number_reflns         1301
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0512
_refine_ls_R_factor_gt           0.0408
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0452P)^2^+0.3789P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0942
_refine_ls_wR_factor_ref         0.0994
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1077
_reflns_number_total             1301
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b03394_si_005.cif
_cod_data_source_block           sam5n
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4038104
_shelx_shelxl_version_number     2016/4
_shelx_estimated_absorpt_t_min   0.814
_shelx_estimated_absorpt_t_max   0.979
_shelx_res_checksum              30896
_shelx_hkl_checksum              52457