Iridium-catalyzed regioselective C‒H sulfonamidation of 1,2,4-thiadiazoles with sulfonyl azides in water
Cao, Xian-Ting; Wei, Su-Ning; Sun, Hao-Tian; Li, Meng; Zheng, Zuo-Ling; Wang, Guannan; RSC Advances 11 (2021) 22000–22004; doi:10.1039/D1RA04450H

data_7243092
_publ_section_title
;
 Iridium-catalyzed regioselective C--H sulfonamidation of
 1,2,4-thiadiazoles with sulfonyl azides in water
;
_journal_issue                   36
_journal_name_full               'RSC Advances'
_journal_page_first              22000
_journal_page_last               22004
_journal_paper_doi               10.1039/D1RA04450H
_journal_volume                  11
_journal_year                    2021
_chemical_formula_moiety         'C21 H17 N3 O2 S2'
_chemical_formula_sum            'C21 H17 N3 O2 S2'
_chemical_formula_weight         407.49
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-12-11
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2021-05-05 deposited with the CCDC.	2021-06-14 downloaded from the CCDC.
;
_cell_angle_alpha                92.4680(10)
_cell_angle_beta                 98.2970(10)
_cell_angle_gamma                99.7790(10)
_cell_formula_units_Z            2
_cell_length_a                   7.46420(10)
_cell_length_b                   11.1508(2)
_cell_length_c                   11.6693(2)
_cell_measurement_reflns_used    5810
_cell_measurement_temperature    293(14)
_cell_measurement_theta_max      73.7550
_cell_measurement_theta_min      5.3760
_cell_volume                     944.85(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293(14)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.955
_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    -11.00  15.00   0.50    0.50    --    0.00 -38.00 -90.00   52
  2  \w     -8.00  21.00   0.50    0.50    --    0.00 -57.00-150.00   58
  3  \w    -25.00   1.00   0.50    0.50    --    0.00 -38.00   0.00   52
  4  \w    -88.00 -24.00   0.50    0.50    --    0.00 -38.00 -90.00  128
  5  \w    -87.00 -50.00   0.50    0.50    --    0.00 -38.00   0.00   74
  6  \w    -89.00 -28.00   0.50    0.50    --    0.00 -57.00-150.00  122
  7  \w     11.00  44.00   0.50    0.50    --   95.20 -61.00  90.00   66
  8  \w     11.00 115.00   0.50    0.50    --   95.20 -61.00  30.00  208
  9  \w      7.00 108.00   0.50    0.50    --   95.20 -30.00-120.00  202
 10  \w     25.00  56.00   0.50    0.50    --   95.20 -82.00  30.00   62
 11  \w     77.00 127.00   0.50    0.50    --   95.20 -82.00  30.00  100
 12  \w     10.00  98.00   0.50    0.50    --   95.20 -61.00-120.00  176
 13  \w     62.00 127.00   0.50    0.50    --   95.20 -82.00-120.00  130
 14  \w     81.00 185.00   0.50    0.50    --   95.20  15.00   0.00  208
 15  \w     61.00 104.00   0.50    0.50    --   95.20 -61.00  90.00   86
 16  \w      7.00  50.00   0.50    0.50    --   95.20 -82.00-120.00   86
 17  \w     15.00 117.00   0.50    0.50    --   95.20 -82.00 150.00  204
 18  \w      6.00  64.00   0.50    0.50    --   95.20 -30.00 150.00  116
 19  \w     87.00 112.00   0.50    0.50    --   95.20 -82.00 -60.00   50
 20  \w     16.00  41.00   0.50    0.50    --   95.20 -77.00 120.00   50
 21  \w     87.00 112.00   0.50    0.50    --   95.20 -77.00 120.00   50
 22  \w    124.00 149.00   0.50    0.50    --   95.20  30.00 -90.00   50
 23  \w     68.00 104.00   0.50    0.50    --   95.20 -30.00 -30.00   72
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0675510000
_diffrn_orient_matrix_UB_12      -0.1070777000
_diffrn_orient_matrix_UB_13      -0.0581204000
_diffrn_orient_matrix_UB_21      0.0496225000
_diffrn_orient_matrix_UB_22      0.0796106000
_diffrn_orient_matrix_UB_23      -0.0994565000
_diffrn_orient_matrix_UB_31      0.1946878000
_diffrn_orient_matrix_UB_32      0.0441108000
_diffrn_orient_matrix_UB_33      0.0679389000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0441
_diffrn_reflns_av_unetI/netI     0.0420
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8588
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.257
_diffrn_reflns_theta_min         3.837
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.745
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.22538
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_description       block
_exptl_crystal_F_000             424
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       0.0061(8)
_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   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3682
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0464
_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^)+(0.0771P)^2^+0.1888P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1285
_refine_ls_wR_factor_ref         0.1330
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3189
_reflns_number_total             3682
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ra04450h2.cif
_cod_data_source_block           xj-1
_cod_database_code               7243092
_reflns_odcompleteness_completeness 99.67
_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 N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15), C17(H17), C18(H18), C20(H20), C21(H21)
2.b Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_shelx_res_checksum              8333
_shelx_shelxl_version_number     2014/7
_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 6.830
_oxdiff_exptl_absorpt_empirical_full_min 0.394