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_1561701
_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_absolute_configuration ad
_chemical_formula_moiety         'C26 H33 N O9 S'
_chemical_formula_sum            'C26 H33 N O9 S'
_chemical_formula_weight         535.59
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-08-01
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6143)
;
_audit_update_record
;
2020-11-05 deposited with the CCDC.	2021-04-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.6693(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   22.5244(2)
_cell_length_b                   10.26708(10)
_cell_length_c                   12.02634(11)
_cell_measurement_reflns_used    13114
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      75.3520
_cell_measurement_theta_min      3.7010
_cell_volume                     2762.39(4)
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(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 0.937
_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    -82.00  -1.00   0.50    0.08    --  -46.87 110.00 -43.00  162
  2  \w     23.00  88.00   0.50    0.08    --   46.87-110.00-138.00  130
  3  \w    -82.00 -15.00   0.50    0.32    --  -88.50 110.00 -43.00  134
  4  \w   -160.00 -82.00   0.50    0.32    --  -88.50-110.00-138.00  156
  5  \w     34.00 107.00   0.50    0.32    --  106.69-110.00-138.00  146
  6  \w    103.00 178.00   0.50    0.32    --  106.69 110.00 -43.00  150
  7  \w   -120.00 -83.00   0.50    0.08    --  -46.87 -57.00  30.00   74
  8  \w   -120.00 -83.00   0.50    0.08    --  -46.87 -57.00-180.00   74
  9  \w   -120.00 -87.00   0.50    0.08    --  -46.87-125.00  30.00   66
 10  \w   -120.00 -83.00   0.50    0.08    --  -46.87 -57.00 -90.00   74
 11  \w     83.00 120.00   0.50    0.08    --   46.87  57.00   0.00   74
 12  \w    -28.00  30.00   0.50    0.08    --   46.87 -19.00 120.00  116
 13  \w    -51.00 -16.00   0.50    0.32    --  -88.50  45.00 -60.00   70
 14  \w    -71.00 -15.00   0.50    0.32    --  -88.50  61.00 150.00  112
 15  \w   -160.00-101.00   0.50    0.32    --  -88.50 -77.00 -90.00  118
 16  \w    -51.00 -16.00   0.50    0.32    --  -88.50  45.00-120.00   70
 17  \w    -51.00 -16.00   0.50    0.32    --  -88.50  45.00   0.00   70
 18  \w    -51.00 -16.00   0.50    0.32    --  -88.50  45.00 150.00   70
 19  \w    -51.00 -16.00   0.50    0.32    --  -88.50  45.00-180.00   70
 20  \w    -51.00 -16.00   0.50    0.32    --  -88.50  45.00 -90.00   70
 21  \w    -51.00 -16.00   0.50    0.32    --  -88.50  45.00  90.00   70
 22  \w    -51.00 -16.00   0.50    0.32    --  -88.50  45.00 120.00   70
 23  \w     34.00  71.00   0.50    0.32    --  106.69 -61.00  30.00   74
 24  \w     34.00 105.00   0.50    0.32    --  106.69 -94.00-120.00  142
 25  \w     34.00 111.00   0.50    0.32    --  106.69-125.00 -30.00  154
 26  \w     34.00  71.00   0.50    0.32    --  106.69 -61.00   0.00   74
 27  \w     34.00 111.00   0.50    0.32    --  106.69-125.00  60.00  154
 28  \w     34.00  71.00   0.50    0.32    --  106.69 -61.00 -90.00   74
 29  \w   -121.00 -32.00   0.50    0.08    --  -46.87 -37.00 -90.00  178
 30  \w   -121.00 -32.00   0.50    0.08    --  -46.87 -37.00-180.00  178
 31  \w     32.00  67.00   0.50    0.08    --   46.87  37.00  60.00   70
 32  \w     32.00 121.00   0.50    0.08    --   46.87  37.00 120.00  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      -0.0067595000
_diffrn_orient_matrix_UB_12      0.0034706000
_diffrn_orient_matrix_UB_13      -0.1289235000
_diffrn_orient_matrix_UB_21      -0.0141181000
_diffrn_orient_matrix_UB_22      0.1467499000
_diffrn_orient_matrix_UB_23      0.0025156000
_diffrn_orient_matrix_UB_31      0.0670384000
_diffrn_orient_matrix_UB_32      0.0312296000
_diffrn_orient_matrix_UB_33      0.0028649000
_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     0.0266
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.937
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            16441
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.938
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.582
_diffrn_reflns_theta_min         3.700
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.482
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.506
_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    1.288
_exptl_crystal_description       plate
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.225
_exptl_crystal_size_mid          0.174
_exptl_crystal_size_min          0.051
_refine_diff_density_max         0.578
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.072(19)
_refine_ls_extinction_coef       0.00072(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     339
_refine_ls_number_reflns         4895
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.0359
_refine_ls_R_factor_gt           0.0355
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0588P)^2^+2.3316P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0938
_refine_ls_wR_factor_ref         0.0944
_reflns_Friedel_coverage         0.891
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.938
_reflns_number_gt                4809
_reflns_number_total             4895
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc01389k2.cif
_cod_data_source_block           hpd185
_cod_original_cell_volume        2762.38(5)
_cod_database_code               1561701
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C H N O S'
_chemical_oxdiff_usercomment     206-3
_shelx_estimated_absorpt_t_max   0.928
_shelx_estimated_absorpt_t_min   0.731
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.928(19)
 0.072(19)
2. 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
3.a Ternary CH refined with riding coordinates:
 C2(H2), C10(H10), C9(H9), C12(H12)
3.b Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B), C7(H7A,H7B), C4(H4A,H4B), C22(H22A,H22B), C21(H21A,H21B),
 C15(H15A,H15B), C20(H20A,H20B), C3(H3A,H3B)
3.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C13(H13)
3.d X=CH2 refined with riding coordinates:
 C19(H19A,H19B)
3.e Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C26(H26A,H26B,H26C), C18(H18A,H18B,H18C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              84125
_shelx_hkl_checksum              9998
_shelx_fab_checksum              32531
_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 1.356
_oxdiff_exptl_absorpt_empirical_full_min 0.815