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_1561706
_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         'C9 H11 N3 O3 S2'
_chemical_formula_sum            'C9 H11 N3 O3 S2'
_chemical_formula_weight         273.33
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-09-29
_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                83.542(3)
_cell_angle_beta                 88.913(2)
_cell_angle_gamma                82.753(2)
_cell_formula_units_Z            2
_cell_length_a                   5.49570(10)
_cell_length_b                   5.8614(2)
_cell_length_c                   18.6487(6)
_cell_measurement_reflns_used    5028
_cell_measurement_temperature    99.98(10)
_cell_measurement_theta_max      74.5980
_cell_measurement_theta_min      2.3880
_cell_volume                     592.13(3)
_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      99.98(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.946
_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   -119.00 -73.00   0.50    0.05    --  -46.62-125.00 143.00   92
  2  \w   -101.00 -23.00   0.50    0.05    --  -46.62 145.00  28.00  156
  3  \w   -119.00 -60.00   0.50    0.05    --  -46.62-145.00 -22.00  118
  4  \w    -86.00 -13.00   0.50    0.05    --  -46.62 125.00-137.00  146
  5  \w     45.00 107.00   0.50    0.05    --   46.62-145.00 -22.00  124
  6  \w     34.00  95.00   0.50    0.05    --   46.62-125.00 143.00  122
  7  \w   -160.00 -73.00   0.50    0.14    --  -88.50-125.00 143.00  174
  8  \w   -152.00 -60.00   0.50    0.14    --  -88.50-145.00 -22.00  184
  9  \w    -86.00 -15.00   0.50    0.14    --  -88.50 125.00-137.00  142
 10  \w   -101.00 -23.00   0.50    0.14    --  -88.50 145.00  28.00  156
 11  \w     34.00 111.00   0.50    0.14    --  106.69-125.00 143.00  154
 12  \w     95.00 178.00   0.50    0.14    --  106.69 125.00-137.00  166
 13  \w     45.00 126.00   0.50    0.14    --  106.69-145.00 -22.00  162
 14  \w     81.00 170.00   0.50    0.14    --  106.69 145.00  28.00  178
 15  \w   -119.00 -83.00   0.50    0.05    --  -46.62 -57.00-120.00   72
 16  \w   -119.00 -83.00   0.50    0.05    --  -46.62 -57.00-150.00   72
 17  \w    -30.00  29.00   0.50    0.05    --  -46.62  19.00   0.00  118
 18  \w   -119.00 -83.00   0.50    0.05    --  -46.62 -57.00 -90.00   72
 19  \w    -30.00  29.00   0.50    0.05    --  -46.62  19.00 150.00  118
 20  \w   -160.00-101.00   0.50    0.14    --  -88.50 -77.00-180.00  118
 21  \w   -160.00-101.00   0.50    0.14    --  -88.50 -77.00 150.00  118
 22  \w   -160.00 -91.00   0.50    0.14    --  -88.50 -61.00 150.00  138
 23  \w    -51.00 -16.00   0.50    0.14    --  -88.50  45.00  60.00   70
 24  \w   -163.00 -73.00   0.50    0.14    --  -88.50 -30.00-180.00  180
 25  \w    -51.00 -16.00   0.50    0.14    --  -88.50  45.00  90.00   70
 26  \w    -51.00 -16.00   0.50    0.14    --  -88.50  45.00   0.00   70
 27  \w     34.00 105.00   0.50    0.14    --  106.69 -94.00 -30.00  142
 28  \w     34.00  71.00   0.50    0.14    --  106.69 -61.00  30.00   74
 29  \w     34.00 101.00   0.50    0.14    --  106.69 -77.00 120.00  134
 30  \w     34.00  71.00   0.50    0.14    --  106.69 -61.00 -90.00   74
 31  \w     89.00 178.00   0.50    0.14    --  106.69  15.00-120.00  178
 32  \w     95.00 178.00   0.50    0.14    --  106.69 125.00 150.00  166
 33  \w     34.00  71.00   0.50    0.14    --  106.69 -61.00-150.00   74
 34  \w     34.00 111.00   0.50    0.14    --  106.69-125.00-120.00  154
 35  \w     89.00 178.00   0.50    0.14    --  106.69  15.00   0.00  178
 36  \w     34.00 101.00   0.50    0.14    --  106.69 -77.00 -30.00  134
 37  \w     34.00  71.00   0.50    0.14    --  106.69 -61.00 120.00   74
 38  \w     34.00  71.00   0.50    0.14    --  106.69 -61.00-180.00   74
 39  \w     32.00 121.00   0.50    0.05    --   46.62  37.00 120.00  178
 40  \w     32.00 121.00   0.50    0.05    --   46.62  37.00 -60.00  178
 41  \w     32.00 121.00   0.50    0.05    --   46.62  37.00-150.00  178
 42  \w     32.00 121.00   0.50    0.05    --   46.62  37.00  30.00  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      -0.0087525000
_diffrn_orient_matrix_UB_12      -0.0507449000
_diffrn_orient_matrix_UB_13      0.0828138000
_diffrn_orient_matrix_UB_21      0.2693399000
_diffrn_orient_matrix_UB_22      0.0448547000
_diffrn_orient_matrix_UB_23      0.0041722000
_diffrn_orient_matrix_UB_31      -0.0850459000
_diffrn_orient_matrix_UB_32      0.2578511000
_diffrn_orient_matrix_UB_33      0.0060321000
_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  0.0479
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            11016
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.591
_diffrn_reflns_theta_min         4.773
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.116
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.568
_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 colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.533
_exptl_crystal_description       plate
_exptl_crystal_F_000             284
_exptl_crystal_size_max          0.159
_exptl_crystal_size_mid          0.104
_exptl_crystal_size_min          0.022
_refine_diff_density_max         0.634
_refine_diff_density_min         -0.495
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2363
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0396
_refine_ls_R_factor_gt           0.0375
_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^)+(0.0550P)^2^+0.3000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0985
_refine_ls_wR_factor_ref         0.1002
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2181
_reflns_number_total             2363
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc01389k2.cif
_cod_data_source_block           hpd223b
_cod_database_code               1561706
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O S'
_chemical_oxdiff_usercomment     thiophene
_reflns_odcompleteness_completeness 100.00
_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:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_shelx_res_checksum              44423
_shelx_hkl_checksum              26856
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.450
_oxdiff_exptl_absorpt_empirical_full_min 0.713