Kinetically-driven reactivity of sulfinylamines enables direct conversion of carboxylic acids to sulfinamides.
Dang, Hang T.; Porey, Arka; Nand, Sachchida; Trevino, Ramon; Manning-Lorino, Patrick; Hughes, William B.; Fremin, Seth O.; Thompson, William T.; Dhakal, Shree Krishna; Arman, Hadi D.; Larionov, Oleg V.; Chemical science 14 (2023) 13384–13391; doi:10.1039/d3sc04727j

data_1570082
_publ_section_title
;
 Kinetically-driven reactivity of sulfinylamines enables direct conversion
 of carboxylic acids to sulfinamides.
;
_journal_issue                   46
_journal_name_full               'Chemical science'
_journal_page_first              13384
_journal_page_last               13391
_journal_paper_doi               10.1039/d3sc04727j
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C11 H14 N2 O S'
_chemical_formula_sum            'C11 H14 N2 O S'
_chemical_formula_weight         222.30
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2022-05-16
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-06-01 deposited with the CCDC.	2023-10-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.395(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.3363(2)
_cell_length_b                   21.0331(7)
_cell_length_c                   8.3324(2)
_cell_measurement_reflns_used    4618
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.9180
_cell_measurement_theta_min      4.2400
_cell_volume                     1105.56(6)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_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  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -21.00  75.00   0.50    0.07    --   46.75 -86.00 100.00  192
  2  \w     34.00 135.00   0.50    0.29    --  106.69 -86.00 100.00  202
  3  \w     34.00  71.00   0.50    0.29    --  106.69 -61.00  90.00   74
  4  \w     35.00  71.00   0.50    0.29    --  106.69 -61.00 120.00   72
  5  \w     34.00 105.00   0.50    0.29    --  106.69 -94.00   0.00  142
  6  \w     39.00  65.00   0.50    0.29    --  106.69 -61.00 -90.00   52
  7  \w     34.00  71.00   0.50    0.29    --  106.69 -61.00-120.00   74
  8  \w     34.00  71.00   0.50    0.29    --  106.69 -61.00 -60.00   74
  9  \w     34.00  71.00   0.50    0.29    --  106.69 -61.00 -30.00   74
 10  \w     34.00 111.00   0.50    0.29    --  106.69-125.00-120.00  154
 11  \w     34.00  71.00   0.50    0.29    --  106.69 -61.00-180.00   74
 12  \w     83.00 119.00   0.50    0.07    --   46.75  57.00-150.00   72
 13  \w    101.00 178.00   0.50    0.29    --  106.69  86.00-141.00  154
 14  \w     91.00 178.00   0.50    0.29    --  106.69  61.00 -90.00  174
 15  \w    -51.00 -16.00   0.50    0.29    --  -88.50  45.00-150.00   70
 16  \w    -75.00  26.00   0.50    0.07    --  -46.75  86.00-141.00  202
 17  \w    -51.00 -16.00   0.50    0.29    --  -88.50  45.00  60.00   70
 18  \w   -116.00 -15.00   0.50    0.29    --  -88.50  86.00-141.00  202
 19  \w   -119.00 -83.00   0.50    0.07    --  -46.75 -57.00-150.00   72
 20  \w   -119.00 -87.00   0.50    0.07    --  -46.75-125.00 -90.00   64
 21  \w   -160.00-101.00   0.50    0.29    --  -88.50 -77.00  30.00  118
 22  \w   -119.00 -83.00   0.50    0.07    --  -46.75 -57.00 120.00   72
 23  \w   -160.00 -79.00   0.50    0.29    --  -88.50 -86.00 100.00  162
 24  \w   -160.00 -91.00   0.50    0.29    --  -88.50 -61.00 150.00  138
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0605969000
_diffrn_orient_matrix_UB_12      -0.0611361000
_diffrn_orient_matrix_UB_13      -0.0866959000
_diffrn_orient_matrix_UB_21      0.2317577000
_diffrn_orient_matrix_UB_22      0.0227187000
_diffrn_orient_matrix_UB_23      0.0077064000
_diffrn_orient_matrix_UB_31      0.0473270000
_diffrn_orient_matrix_UB_32      -0.0333444000
_diffrn_orient_matrix_UB_33      0.1640817000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0511
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            10390
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.442
_diffrn_reflns_theta_min         4.204
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.394
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.804
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_description       plate
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.183
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.062
_refine_diff_density_max         0.475
_refine_diff_density_min         -0.574
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2229
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0417
_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^)+(0.0400P)^2^+1.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1036
_refine_ls_wR_factor_ref         0.1050
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2070
_reflns_number_total             2229
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc04727j2.cif
_cod_data_source_block           hpd539
_cod_depositor_comments
'Adding full bibliography for 1570081--1570086.cif.'
_cod_original_cell_volume        1105.55(6)
_cod_database_code               1570082
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O S'
_chemical_oxdiff_usercomment     'HDC 577-5'
_shelx_estimated_absorpt_t_max   0.866
_shelx_estimated_absorpt_t_min   0.668
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C2(H2A), C3(H3), C8(H8), C9(H9), C4(H4)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_shelx_res_checksum              49890
_olex2_exptl_crystal_mounting_method 'nylon loop'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 1.387
_oxdiff_exptl_absorpt_empirical_full_min 0.705