Photocatalytic decarboxylative amidosulfonation enables direct transformation of carboxylic acids to sulfonamides
Nguyen, Vu T.; Haug, Graham C.; Nguyen, Viet D.; Vuong, Ngan T. H.; Arman, Hadi D.; Larionov, Oleg V.; Chemical Science  (2021) –; doi:10.1039/D1SC01389K

data_1561699
_publ_section_title
;
 Photocatalytic decarboxylative amidosulfonation enables direct
 transformation of carboxylic acids to sulfonamides
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC01389K
_journal_year                    2021
_chemical_formula_moiety         'C14 H21 N O5 S'
_chemical_formula_sum            'C14 H21 N O5 S'
_chemical_formula_weight         315.38
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2020-08-10
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.10.09 svn.r3662 for Rigaku Oxford Diffraction, GUI svn.r5959)
;
_audit_update_record
;
2020-11-05 deposited with the CCDC.	2021-04-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.078(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   26.9877(4)
_cell_length_b                   5.72560(10)
_cell_length_c                   9.8987(2)
_cell_measurement_reflns_used    8640
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.4470
_cell_measurement_theta_min      3.2630
_cell_volume                     1529.55(5)
_computing_cell_refinement       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_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 0.972
_diffrn_measured_fraction_theta_max 0.918
_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    -42.00  27.00   0.50    0.05    --  -46.87  36.00-127.00  138
  2  \w    -80.00 -15.00   0.50    0.10    --  -88.50  89.00  59.00  130
  3  \w     34.00 108.00   0.50    0.10    --  106.69-112.00-140.00  148
  4  \w     92.00 178.00   0.50    0.10    --  106.69  36.00-127.00  172
  5  \w   -120.00 -87.00   0.50    0.05    --  -46.87-125.00 -60.00   66
  6  \w   -120.00 -87.00   0.50    0.05    --  -46.87-125.00-150.00   66
  7  \w   -120.00 -83.00   0.50    0.05    --  -46.87 -57.00 -60.00   74
  8  \w    -28.00  30.00   0.50    0.05    --   46.87 -19.00 -90.00  116
  9  \w    -51.00 -16.00   0.50    0.10    --  -88.50  45.00 -60.00   70
 10  \w    -51.00 -16.00   0.50    0.10    --  -88.50  45.00-150.00   70
 11  \w    -51.00 -16.00   0.50    0.10    --  -88.50  45.00 -90.00   70
 12  \w     34.00  71.00   0.50    0.10    --  106.69 -61.00 120.00   74
 13  \w     34.00 101.00   0.50    0.10    --  106.69 -77.00 -60.00  134
 14  \w     34.00  71.00   0.50    0.10    --  106.69 -61.00   0.00   74
 15  \w   -120.00 -83.00   0.50    0.05    --  -46.87 -57.00  90.00   74
 16  \w   -120.00 -83.00   0.50    0.05    --  -46.87 -57.00   0.00   74
 17  \w     32.00 121.00   0.50    0.05    --   46.87  37.00  90.00  178
 18  \w     32.00 121.00   0.50    0.05    --   46.87  37.00-150.00  178
 19  \w   -160.00-132.00   0.50    0.10    --  -88.50 -61.00 -30.00   56
 20  \w     83.00 108.00   0.50    0.05    --   46.87  57.00  30.00   50
 21  \w    -71.00 -15.00   0.50    0.10    --  -88.50  61.00 -60.00  112
 22  \w     68.00  98.00   0.50    0.10    --  106.69 -77.00  90.00   60
 23  \w     93.00 119.00   0.50    0.10    --  106.69  30.00   0.00   52
 24  \w    143.00 169.00   0.50    0.10    --  106.69  30.00   0.00   52
 25  \w     39.00  65.00   0.50    0.10    --  106.69 -77.00  90.00   52
 26  \w     37.00  66.00   0.50    0.10    --  106.69 -61.00  90.00   58
 27  \w    111.00 136.00   0.50    0.10    --  106.69  36.00-127.00   50
 28  \w   -120.00 -83.00   0.50    0.05    --  -46.87 -57.00 -30.00   74
 29  \w     32.00 121.00   0.50    0.05    --   46.87  37.00 150.00  178
 30  \w     32.00  61.00   0.50    0.05    --   46.87  37.00  30.00   58
 31  \w     32.00 121.00   0.50    0.05    --   46.87  37.00 -60.00  178
;
_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      0.0516639000
_diffrn_orient_matrix_UB_12      -0.0177053000
_diffrn_orient_matrix_UB_13      -0.0651874000
_diffrn_orient_matrix_UB_21      0.0011624000
_diffrn_orient_matrix_UB_22      -0.2637480000
_diffrn_orient_matrix_UB_23      0.0307031000
_diffrn_orient_matrix_UB_31      -0.0242425000
_diffrn_orient_matrix_UB_32      -0.0503246000
_diffrn_orient_matrix_UB_33      -0.1379405000
_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  0.0322
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.918
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            14613
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.918
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.280
_diffrn_reflns_theta_min         3.275
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.075
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.563
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.63a (Rigaku Oxford Diffraction, 2019)
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 white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.204
_exptl_crystal_size_mid          0.136
_exptl_crystal_size_min          0.079
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.432
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2942
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0350
_refine_ls_R_factor_gt           0.0326
_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^)+(0.0439P)^2^+0.7163P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0843
_refine_ls_wR_factor_ref         0.0863
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2713
_reflns_number_total             2942
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc01389k2.cif
_cod_data_source_block           hpd192c
_cod_database_code               1561699
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H S O N'
_chemical_oxdiff_usercomment     'VNY 206-2'
_reflns_odcompleteness_completeness 96.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C5(H5A,H5B), C2(H2A,H2B), C6(H6A,H6B), C1(H1A,H1B), C4(H4A,H4B)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C12(H12), C8(H8)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C13(H13A,H13B,H13C)
;
_shelx_res_checksum              91846
_shelx_hkl_checksum              37929
_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
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 1.421
_oxdiff_exptl_absorpt_empirical_full_min 0.743