Synthesis of chiral <i>N</i>-free sulfinamides by asymmetric condensation of stable sulfinates and ammonium salts.
Xiong, Qin; Liao, Minghong; Wang, Gangyu; Shi, Hai; Wu, Xingxing; Chemical communications (Cambridge, England) 61 (2025) 3017–3020; doi:10.1039/d4cc06395c

data_7134170
_publ_section_title
;
 Synthesis of chiral <i>N</i>-free sulfinamides by asymmetric condensation
 of stable sulfinates and ammonium salts.
;
_journal_issue                   14
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              3017
_journal_page_last               3020
_journal_paper_doi               10.1039/d4cc06395c
_journal_volume                  61
_journal_year                    2025
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C7 H9 N O S'
_chemical_formula_sum            'C7 H9 N O S'
_chemical_formula_weight         155.21
_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_date             2024-01-30
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-01-31 deposited with the CCDC.	2025-01-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.9512(6)
_cell_length_b                   6.4395(8)
_cell_length_c                   24.625(3)
_cell_measurement_reflns_used    1846
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.465
_cell_measurement_theta_min      2.491
_cell_volume                     785.13(17)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1247
_diffrn_reflns_av_unetI/netI     0.0993
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            3718
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.006
_diffrn_reflns_theta_max         25.006
_diffrn_reflns_theta_min         3.270
_exptl_absorpt_coefficient_mu    0.341
_exptl_absorpt_correction_T_max  0.9667
_exptl_absorpt_correction_T_min  0.8533
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.324
_refine_diff_density_min         -0.371
_refine_diff_density_rms         0.072
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.1(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.143
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     93
_refine_ls_number_reflns         1374
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.143
_refine_ls_R_factor_all          0.0729
_refine_ls_R_factor_gt           0.0676
_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^)+(0.0661P)^2^+0.5559P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1703
_refine_ls_wR_factor_ref         0.1735
_reflns_Friedel_coverage         0.624
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                1255
_reflns_number_total             1374
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc06395c2.cif
_cod_data_source_block           230622b
_cod_depositor_comments          'Adding full bibliography for 7134170.cif.'
_cod_original_cell_volume        785.11(16)
_cod_database_code               7134170
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.967
_shelx_estimated_absorpt_t_min   0.853
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.9(3)
 0.1(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All N(H,H) groups
3.a Riding coordinates:
 N1(H1A,H1B)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6)
3.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_shelx_res_checksum              10251
_olex2_submission_special_instructions 'No special instructions were received'