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_1561703
_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 H17 N O4 S'
_chemical_formula_sum            'C9 H17 N O4 S'
_chemical_formula_weight         235.29
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-07-24
_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                 91.6050(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.4344(2)
_cell_length_b                   6.10100(10)
_cell_length_c                   9.77720(10)
_cell_measurement_reflns_used    8836
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.3360
_cell_measurement_theta_min      2.4030
_cell_volume                     1099.19(2)
_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 0.999
_diffrn_measured_fraction_theta_max 0.959
_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   -123.00 -29.00   0.50    0.05    --  -46.87 -15.00 113.00  188
  2  \w    -29.00  29.00   0.50    0.05    --  -46.87  15.00 -76.00  116
  3  \w     29.00 123.00   0.50    0.05    --   46.87  15.00 -76.00  188
  4  \w   -164.00 -71.00   0.50    0.05    --  -88.50 -15.00 113.00  186
  5  \w     89.00 178.00   0.50    0.05    --  106.69  15.00 -76.00  178
  6  \w   -120.00 -87.00   0.50    0.05    --  -46.87-125.00 120.00   66
  7  \w     83.00 120.00   0.50    0.05    --   46.87  57.00-180.00   74
  8  \w    -28.00  29.00   0.50    0.05    --   46.87 -15.00 113.00  114
  9  \w    -28.00  30.00   0.50    0.05    --   46.87 -19.00   0.00  116
 10  \w    -51.00 -16.00   0.50    0.05    --  -88.50  45.00-150.00   70
 11  \w    -51.00 -16.00   0.50    0.05    --  -88.50  45.00-120.00   70
 12  \w    -71.00 -15.00   0.50    0.05    --  -88.50  61.00 120.00  112
 13  \w    -51.00 -16.00   0.50    0.05    --  -88.50  45.00 -90.00   70
 14  \w    -71.00 -15.00   0.50    0.05    --  -88.50  61.00  60.00  112
 15  \w    -51.00 -16.00   0.50    0.05    --  -88.50  45.00 150.00   70
 16  \w   -160.00-100.00   0.50    0.05    --  -88.50 -94.00-120.00  120
 17  \w     34.00 111.00   0.50    0.05    --  106.69-125.00  30.00  154
 18  \w     34.00 105.00   0.50    0.05    --  106.69 -94.00  60.00  142
 19  \w     34.00  71.00   0.50    0.05    --  106.69 -61.00  30.00   74
 20  \w     34.00  71.00   0.50    0.05    --  106.69 -61.00 -90.00   74
 21  \w     34.00  71.00   0.50    0.05    --  106.69 -61.00 150.00   74
 22  \w     34.00  71.00   0.50    0.05    --  106.69 -61.00 -60.00   74
 23  \w     34.00  71.00   0.50    0.05    --  106.69 -61.00-150.00   74
 24  \w     34.00 101.00   0.50    0.05    --  106.69 -77.00 150.00  134
 25  \w     32.00 121.00   0.50    0.05    --   46.87  37.00  90.00  178
 26  \w     32.00 121.00   0.50    0.05    --   46.87  37.00-180.00  178
 27  \w     32.00 121.00   0.50    0.05    --   46.87  37.00 -90.00  178
 28  \w     34.00  96.00   0.50    0.05    --   46.87-125.00  60.00  124
 29  \w     32.00 109.00   0.50    0.05    --   46.87  37.00 -30.00  154
 30  \w     32.00 121.00   0.50    0.05    --   46.87  37.00   0.00  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      0.0819829000
_diffrn_orient_matrix_UB_12      -0.0472551000
_diffrn_orient_matrix_UB_13      -0.0045591000
_diffrn_orient_matrix_UB_21      0.0037903000
_diffrn_orient_matrix_UB_22      -0.0158485000
_diffrn_orient_matrix_UB_23      0.1573095000
_diffrn_orient_matrix_UB_31      -0.0159123000
_diffrn_orient_matrix_UB_32      -0.2475282000
_diffrn_orient_matrix_UB_33      -0.0091910000
_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     0.0191
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            12863
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.521
_diffrn_reflns_theta_min         2.398
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.613
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.397
_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    1.422
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.301
_exptl_crystal_size_mid          0.217
_exptl_crystal_size_min          0.105
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.519
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2219
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0369
_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^)+(0.0580P)^2^+0.4372P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1014
_refine_ls_wR_factor_ref         0.1034
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2062
_reflns_number_total             2219
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc01389k2.cif
_cod_data_source_block           hpd170
_cod_database_code               1561703
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H S O N'
_chemical_oxdiff_usercomment     'VNY 184-12'
_shelx_estimated_absorpt_t_max   0.771
_shelx_estimated_absorpt_t_min   0.507
_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, All C(H,H,H,H) groups
2. Others
 Fixed Sof: H1BC(0.65) H1BD(0.65) H1AA(0.35) H1AB(0.35) C4B(0.75) H4BA(0.75)
 H4BB(0.75) C3B(0.75) H3BA(0.75) H3BB(0.75) C2B(0.65) H2BA(0.65) H2BB(0.65)
 C2A(0.35) H2AA(0.35) H2AB(0.35) C4A(0.25) H4AA(0.25) H4AB(0.25) C3A(0.25)
 H3AA(0.25) H3AB(0.25)
3.a Ternary CH refined with riding coordinates:
 C5(H5)
3.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C9(H9A,H9B), C7(H7A,H7B), C8(H8A,H8B), C1(H1BC,H1BD), C1(H1AA,
 H1AB), C4B(H4BA,H4BB), C3B(H3BA,H3BB), C2B(H2BA,H2BB), C2A(H2AA,H2AB),
 C4A(H4AA,H4AB), C3A(H3AA,H3AB)
;
_shelx_res_checksum              94613
_shelx_hkl_checksum              59465
_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
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 1.305
_oxdiff_exptl_absorpt_empirical_full_min 0.751