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_1561707
_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         'C17 H23 N O2 S'
_chemical_formula_sum            'C17 H23 N O2 S'
_chemical_formula_weight         305.42
_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
_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                 110.571(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.0325(4)
_cell_length_b                   6.26860(10)
_cell_length_c                   18.2532(5)
_cell_measurement_reflns_used    5571
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.2670
_cell_measurement_theta_min      5.1710
_cell_volume                     1503.25(7)
_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      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 1.000
_diffrn_measured_fraction_theta_max 0.990
_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   -122.00 -45.00   0.50    0.21    --  -46.75 -25.00-150.00  154
  2  \w    -23.00  30.00   0.50    0.21    --  -46.75  25.00  13.00  106
  3  \w    -22.00   3.00   0.50    0.21    --   46.75 -25.00-150.00   50
  4  \w     58.00 100.00   0.50    0.21    --   46.75  25.00  13.00   84
  5  \w   -111.00 -81.00   0.50    0.83    --  -88.50 -25.00-150.00   60
  6  \w     91.00 178.00   0.50    0.83    --  106.69  25.00  13.00  174
  7  \w    -29.00  27.00   0.50    0.21    --  -46.75  19.00 150.00  112
  8  \w     85.00 117.00   0.50    0.21    --   46.75  57.00 -60.00   64
  9  \w    -51.00 -19.00   0.50    0.83    --  -88.50  45.00 150.00   64
 10  \w    -44.00 -19.00   0.50    0.83    --  -88.50  45.00 -60.00   50
 11  \w    -50.00 -25.00   0.50    0.83    --  -88.50  45.00-180.00   50
 12  \w    -50.00 -16.00   0.50    0.83    --  -88.50  45.00  90.00   68
 13  \w    -51.00 -18.00   0.50    0.83    --  -88.50  45.00   0.00   66
 14  \w    -59.00 -33.00   0.50    0.83    --  -88.50  61.00-150.00   52
 15  \w     86.00 111.00   0.50    0.83    --  106.69-125.00-150.00   50
 16  \w     65.00 105.00   0.50    0.83    --  106.69 -94.00   0.00   80
 17  \w     36.00  64.00   0.50    0.83    --  106.69-125.00-150.00   56
 18  \w     35.00  66.00   0.50    0.83    --  106.69 -61.00-150.00   62
 19  \w     34.00  59.00   0.50    0.83    --  106.69 -61.00  60.00   50
 20  \w     60.00  98.00   0.50    0.83    --  106.69 -77.00  90.00   76
 21  \w     63.00  93.00   0.50    0.83    --  106.69 -77.00  60.00   60
 22  \w     34.00  59.00   0.50    0.83    --  106.69 -61.00  90.00   50
 23  \w     34.00  70.00   0.50    0.83    --  106.69 -61.00-120.00   72
 24  \w     76.00 105.00   0.50    0.83    --  106.69 -94.00-150.00   58
 25  \w     46.00  72.00   0.50    0.83    --  106.69 -77.00 -60.00   52
 26  \w     74.00 100.00   0.50    0.83    --  106.69 -77.00 -60.00   52
 27  \w     36.00  61.00   0.50    0.83    --  106.69 -94.00-150.00   50
 28  \w     34.00  62.00   0.50    0.83    --  106.69 -61.00 -90.00   56
 29  \w     48.00  94.00   0.50    0.83    --  106.69 -77.00 -90.00   92
 30  \w     34.00  59.00   0.50    0.83    --  106.69 -61.00 -60.00   50
 31  \w     66.00  92.00   0.50    0.83    --  106.69 -77.00 120.00   52
 32  \w     37.00  70.00   0.50    0.83    --  106.69 -61.00   0.00   66
 33  \w    110.00 135.00   0.50    0.83    --  106.69  25.00  14.00   50
 34  \w     87.00 113.00   0.50    0.21    --   46.75  57.00 -90.00   52
 35  \w    -57.00 -20.00   0.50    0.83    --  -88.50  61.00  60.00   74
 36  \w   -144.00-118.00   0.50    0.83    --  -88.50 -77.00  90.00   52
 37  \w   -151.00-102.00   0.50    0.83    --  -88.50 -77.00  30.00   98
 38  \w    117.00 143.00   0.50    0.83    --  106.69 125.00  60.00   52
 39  \w     57.00  83.00   0.50    0.83    --  106.69 -77.00-180.00   52
 40  \w    153.00 178.00   0.50    0.83    --  106.69 125.00  60.00   50
 41  \w     80.00 105.00   0.50    0.83    --  106.69 -94.00  90.00   50
 42  \w     34.00  60.00   0.50    0.83    --  106.69 -61.00  30.00   52
;
_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      0.0905970000
_diffrn_orient_matrix_UB_12      -0.0296000000
_diffrn_orient_matrix_UB_13      -0.0281679000
_diffrn_orient_matrix_UB_21      -0.0668350000
_diffrn_orient_matrix_UB_22      0.0742446000
_diffrn_orient_matrix_UB_23      -0.0825608000
_diffrn_orient_matrix_UB_31      0.0329050000
_diffrn_orient_matrix_UB_32      0.2322816000
_diffrn_orient_matrix_UB_33      0.0228102000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_unetI/netI     0.0198
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            5689
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.687
_diffrn_reflns_theta_min         3.448
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.941
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.807
_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    1.350
_exptl_crystal_description       plate
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.151
_exptl_crystal_size_mid          0.118
_exptl_crystal_size_min          0.023
_refine_diff_density_max         0.399
_refine_diff_density_min         -0.467
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         5689
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0445
_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^+1.2000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1072
_refine_ls_wR_factor_ref         0.1096
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5110
_reflns_number_total             5689
_reflns_threshold_expression     'I > 2\s(I)'
_twin_special_details
;
Component 2 rotated by -179.7531\% 
 around [0.40 0.00 0.91] (reciprocal) or [0.71 -0.00 0.71] (direct)
;
_cod_data_source_file            d1sc01389k2.cif
_cod_data_source_block           hpd188b_twin1_hklf4
_cod_database_code               1561707
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C H N S O'
_chemical_oxdiff_usercomment     194-02
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.6671(10)
 0.3329(10)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
3.a Ternary CH refined with riding coordinates:
 C12(H12), C10(H10), C15(H15)
3.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C1(H1A,H1B), C9(H9A,H9B), C16(H16A,H16B), C13(H13A,H13B),
 C17(H17A,H17B), C11(H11A,H11B)
3.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C3(H3), C7(H7), C6(H6), C5(H5), C4(H4)
;
_shelx_res_checksum              20272
_shelx_hkl_checksum              20048
_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 1.638
_oxdiff_exptl_absorpt_empirical_full_min 0.784
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2