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_1561704
_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 H25 N O2 S'
_chemical_formula_sum            'C14 H25 N O2 S'
_chemical_formula_weight         271.41
_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             2020-08-11
_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                 94.9930(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.47310(10)
_cell_length_b                   19.8101(2)
_cell_length_c                   11.04280(10)
_cell_measurement_reflns_used    9905
_cell_measurement_temperature    99.98(10)
_cell_measurement_theta_max      75.6390
_cell_measurement_theta_min      4.4600
_cell_volume                     1410.68(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 n/a (Sheldrick, 2015)'
_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 0.999
_diffrn_measured_fraction_theta_max 0.972
_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   -102.00 -24.00   0.50    0.05    --  -46.87 147.00 -43.00  156
  2  \w   -120.00 -74.00   0.50    0.05    --  -46.87-124.00  71.00   92
  3  \w   -120.00 -58.00   0.50    0.05    --  -46.87-147.00 -93.00  124
  4  \w     46.00 108.00   0.50    0.05    --   46.87-147.00 -93.00  124
  5  \w     34.00  95.00   0.50    0.05    --   46.87-124.00  71.00  122
  6  \w   -101.00 -24.00   0.50    0.11    --  -88.50 147.00 -43.00  154
  7  \w   -160.00 -74.00   0.50    0.11    --  -88.50-124.00  71.00  172
  8  \w     46.00 128.00   0.50    0.11    --  106.69-147.00 -93.00  164
  9  \w     34.00 111.00   0.50    0.11    --  106.69-124.00  71.00  154
 10  \w   -120.00 -83.00   0.50    0.05    --  -46.87 -57.00  60.00   74
 11  \w   -120.00 -83.00   0.50    0.05    --  -46.87 -57.00 -30.00   74
 12  \w     83.00 120.00   0.50    0.05    --   46.87  57.00-180.00   74
 13  \w     83.00 120.00   0.50    0.05    --   46.87  57.00 -30.00   74
 14  \w    -51.00 -16.00   0.50    0.11    --  -88.50  45.00 -30.00   70
 15  \w    -51.00 -16.00   0.50    0.11    --  -88.50  45.00  30.00   70
 16  \w    -51.00 -16.00   0.50    0.11    --  -88.50  45.00   0.00   70
 17  \w   -151.00 -58.00   0.50    0.11    --  -88.50-147.00 -93.00  186
 18  \w     34.00 105.00   0.50    0.11    --  106.69 -94.00-120.00  142
 19  \w     34.00 105.00   0.50    0.11    --  106.69 -94.00 -90.00  142
 20  \w     89.00 178.00   0.50    0.11    --  106.69  15.00  90.00  178
 21  \w     89.00 178.00   0.50    0.11    --  106.69  15.00 150.00  178
 22  \w     34.00 101.00   0.50    0.11    --  106.69 -77.00  60.00  134
 23  \w     34.00  71.00   0.50    0.11    --  106.69 -61.00  60.00   74
 24  \w     34.00  71.00   0.50    0.11    --  106.69 -61.00  90.00   74
 25  \w     80.00 168.00   0.50    0.11    --  106.69 147.00 -43.00  176
 26  \w   -120.00 -83.00   0.50    0.05    --  -46.87 -57.00 -90.00   74
 27  \w     32.00  77.00   0.50    0.05    --   46.87  37.00 -60.00   90
 28  \w     32.00 121.00   0.50    0.05    --   46.87  37.00  90.00  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      -0.0302974000
_diffrn_orient_matrix_UB_12      -0.0280873000
_diffrn_orient_matrix_UB_13      0.1273560000
_diffrn_orient_matrix_UB_21      -0.0330355000
_diffrn_orient_matrix_UB_22      0.0722086000
_diffrn_orient_matrix_UB_23      0.0462883000
_diffrn_orient_matrix_UB_31      -0.2346589000
_diffrn_orient_matrix_UB_32      -0.0065628000
_diffrn_orient_matrix_UB_33      -0.0354373000
_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  0.0340
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            16425
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.467
_diffrn_reflns_theta_min         4.464
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.992
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.676
_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    1.278
_exptl_crystal_description       plate
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.106
_exptl_crystal_size_min          0.055
_refine_diff_density_max         0.354
_refine_diff_density_min         -0.422
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     169
_refine_ls_number_reflns         2875
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0339
_refine_ls_R_factor_gt           0.0321
_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^)+(0.0459P)^2^+0.5650P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0856
_refine_ls_wR_factor_ref         0.0871
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2706
_reflns_number_total             2875
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc01389k2.cif
_cod_data_source_block           hpd197
_cod_database_code               1561704
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O S'
_chemical_oxdiff_usercomment     VNY-199-3
_shelx_estimated_absorpt_t_max   0.898
_shelx_estimated_absorpt_t_min   0.625
_reflns_odcompleteness_completeness 99.96
_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 Ternary CH refined with riding coordinates:
 C8(H8), C3(H3), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C7(H7A,H7B), C6(H6A,H6B), C10(H10A,H10B), C4(H4A,H4B), C9(H9A,H9B)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C)
;
_shelx_res_checksum              10973
_shelx_hkl_checksum              39904
_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 1.215
_oxdiff_exptl_absorpt_empirical_full_min 0.871