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_1561705
_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         'C12 H17 N O3 S'
_chemical_formula_sum            'C12 H17 N O3 S'
_chemical_formula_weight         255.32
_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   mixed
_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                 105.544(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.4965(2)
_cell_length_b                   24.4849(12)
_cell_length_c                   9.7713(4)
_cell_measurement_reflns_used    4354
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.8620
_cell_measurement_theta_min      5.0090
_cell_volume                     1266.94(10)
_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 n/a (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 0.992
_diffrn_measured_fraction_theta_max 0.958
_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    -31.00  28.00   0.50    0.15    --  -45.87  39.00 125.00  118
  2  \w   -119.00 -32.00   0.50    0.15    --  -45.87 -39.00 -28.00  174
  3  \w     16.00  45.00   0.50    0.15    --   45.87 -39.00 -28.00   58
  4  \w   -111.00 -75.00   0.50    0.60    --  -88.50 -39.00 -28.00   72
  5  \w   -162.00-136.00   0.50    0.60    --  -88.50 -39.00 -28.00   52
  6  \w    -44.00 -19.00   0.50    0.60    --  -88.50  39.00 125.00   50
  7  \w     93.00 173.00   0.50    0.60    --  106.69  39.00 125.00  160
  8  \w   -117.00 -88.00   0.50    0.15    --  -45.87-125.00 120.00   58
  9  \w     34.00  82.00   0.50    0.15    --   45.87-125.00   0.00   96
 10  \w     83.00 117.00   0.50    0.15    --   45.87  57.00  60.00   68
 11  \w     56.00  83.00   0.50    0.15    --   45.87  39.00 125.00   54
 12  \w    -46.00 -16.00   0.50    0.60    --  -88.50  45.00  60.00   60
 13  \w   -125.00-100.00   0.50    0.60    --  -88.50 -94.00  90.00   50
 14  \w    -64.00 -16.00   0.50    0.60    --  -88.50  57.00 -79.96   96
 15  \w    -47.00 -16.00   0.50    0.60    --  -88.50  45.00 -60.00   62
 16  \w    -49.00 -17.00   0.50    0.60    --  -88.50  45.00-150.00   64
 17  \w    -42.00 -17.00   0.50    0.60    --  -88.50  45.00-180.00   50
 18  \w     34.00  66.00   0.50    0.60    --  106.69 -61.00 120.00   64
 19  \w     57.00 107.00   0.50    0.60    --  106.69-102.00 119.40  100
 20  \w     35.00  66.00   0.50    0.60    --  106.69-125.00  60.00   62
 21  \w     77.00 111.00   0.50    0.60    --  106.69-125.00  60.00   68
 22  \w    112.00 162.00   0.50    0.60    --  106.69  15.00  60.00  100
 23  \w     38.00  65.00   0.50    0.60    --  106.69 -60.00-173.67   54
 24  \w     41.00  69.00   0.50    0.60    --  106.69 -61.00-120.00   56
 25  \w     76.00 105.00   0.50    0.60    --  106.69-125.00-150.00   58
 26  \w     36.00  75.00   0.50    0.60    --  106.69-125.00-150.00   78
 27  \w     72.00 105.00   0.50    0.60    --  106.69 -94.00-150.00   66
 28  \w     46.00  74.00   0.50    0.60    --  106.69-114.00   3.26   56
 29  \w     81.00 109.00   0.50    0.60    --  106.69-114.00   3.26   56
 30  \w     45.00  71.00   0.50    0.60    --  106.69 -61.00-150.00   52
 31  \w     56.00  83.00   0.50    0.60    --  106.69 -94.00  90.00   54
 32  \w     89.00 177.00   0.50    0.60    --  106.69  15.00-120.00  176
 33  \w     43.00  70.00   0.50    0.60    --  106.69 -77.00  60.00   54
 34  \w     40.00 106.00   0.50    0.60    --  106.69-102.00  73.52  132
 35  \w    -58.00 -32.00   0.50    0.15    --  -45.87 -38.00 -27.00   52
 36  \w   -123.00 -97.00   0.50    0.60    --  -88.50-125.00  60.00   52
 37  \w   -156.00-129.00   0.50    0.60    --  -88.50 -94.00 -60.00   54
 38  \w     56.00 101.00   0.50    0.60    --  106.69 -77.00-120.00   90
;
_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      0.1257887000
_diffrn_orient_matrix_UB_12      0.0551735000
_diffrn_orient_matrix_UB_13      0.0520578000
_diffrn_orient_matrix_UB_21      0.2554377000
_diffrn_orient_matrix_UB_22      -0.0290586000
_diffrn_orient_matrix_UB_23      0.0580662000
_diffrn_orient_matrix_UB_31      0.0598348000
_diffrn_orient_matrix_UB_32      0.0082206000
_diffrn_orient_matrix_UB_33      -0.1439234000
_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  0.0467
_diffrn_reflns_av_unetI/netI     0.0397
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            11078
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.662
_diffrn_reflns_theta_min         3.610
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.256
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.533
_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    1.339
_exptl_crystal_description       plate
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.174
_exptl_crystal_size_mid          0.162
_exptl_crystal_size_min          0.044
_refine_diff_density_max         0.558
_refine_diff_density_min         -0.663
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         2554
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0531
_refine_ls_R_factor_gt           0.0486
_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^)+(0.0350P)^2^+2.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1217
_refine_ls_wR_factor_ref         0.1239
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2308
_reflns_number_total             2554
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc01389k2.cif
_cod_data_source_block           hpd191
_cod_database_code               1561705
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H S O N'
_chemical_oxdiff_usercomment     203-A3
_shelx_estimated_absorpt_t_max   0.907
_shelx_estimated_absorpt_t_min   0.695
_reflns_odcompleteness_completeness 99.06
_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, All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C6(H6A,H6B), C4(H4A,H4B), C1(H1A,H1B), C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C11(H11), C12(H12), C10(H10), C9(H9)
;
_shelx_res_checksum              97494
_shelx_hkl_checksum              80866
_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 1.296
_oxdiff_exptl_absorpt_empirical_full_min 0.775