Switching the site-selectivity of C–H activation in aryl sulfonamides containing strongly coordinating N-heterocycles
Dong, Yi; Zhang, Xuepeng; Chen, Jiajing; Zou, Wenxing; Lin, Songwen; Xu, Heng; Chemical Science  (2019) –; doi:10.1039/C9SC03691A

data_1552180
_publ_section_title
;
 Switching the site-selectivity of C--H activation in aryl sulfonamides
 containing strongly coordinating N-heterocycles
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/C9SC03691A
_journal_year                    2019
_chemical_formula_moiety         'C17 H15 F3 N2 O8 S2'
_chemical_formula_sum            'C17 H15 F3 N2 O8 S2'
_chemical_formula_weight         496.43
_chemical_melting_point          443
_chemical_name_systematic
'dimethyl 2-(5-(N-acetylsulfamoyl)-2-(thiazol-2-yl)-4-(trifluoromethoxy)phenyl)malonate'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-09-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-10-19 deposited with the CCDC.    2019-08-12 downloaded from the CCDC.
;
_cell_angle_alpha                95.266(3)
_cell_angle_beta                 100.867(3)
_cell_angle_gamma                92.113(3)
_cell_formula_units_Z            2
_cell_length_a                   8.0043(3)
_cell_length_b                   10.7993(4)
_cell_length_c                   12.4643(5)
_cell_measurement_reflns_used    4368
_cell_measurement_temperature    296.00(18)
_cell_measurement_theta_max      71.1810
_cell_measurement_theta_min      4.0970
_cell_volume                     1052.02(7)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      296.00(18)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2137
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.968
_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    -68.00  13.00   1.00    1.00    --  -40.81  57.00 150.00   81
  2  \w   -110.00 -21.00   1.00    1.00    --  -40.81 -57.00-150.00   89
  3  \w    -69.00  30.00   1.00    1.00    --  -40.81  57.00   0.00   99
  4  \w      1.00  27.00   1.00    1.00    --   40.81 -99.00  90.00   26
  5  \w     95.00 120.00   1.00    1.00    --  100.91 125.00  30.00   25
  6  \w     94.00 159.00   1.00    1.00    --  100.91 125.00 150.00   65
  7  \w     29.00  55.00   1.00    1.00    --  100.91 -45.00  60.00   26
  8  \w     82.00 170.00   1.00    1.00    --  100.91  30.00 150.00   88
  9  \w     84.00 171.00   1.00    1.00    --  100.91  61.00-150.00   87
 10  \w     42.00 110.00   1.00    1.00    --  100.91 -95.00  90.00   68
 11  \w    113.00 169.00   1.00    1.00    --  100.91 125.00  90.00   56
 12  \w     60.00 127.00   1.00    1.00    --  100.91 -45.00  60.00   67
 13  \w     52.00 113.00   1.00    1.00    --  100.91-125.00  60.00   61
 14  \w     91.00 118.00   1.00    1.00    --  100.91-125.00 -60.00   27
 15  \w     45.00 130.00   1.00    1.00    --  100.91 -77.00-180.00   85
 16  \w     43.00 119.00   1.00    1.00    --  100.91 -30.00-180.00   76
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0376374000
_diffrn_orient_matrix_UB_12      0.1048457000
_diffrn_orient_matrix_UB_13      0.0951650000
_diffrn_orient_matrix_UB_21      -0.1887318000
_diffrn_orient_matrix_UB_22      -0.0073366000
_diffrn_orient_matrix_UB_23      0.0105169000
_diffrn_orient_matrix_UB_31      0.0386078000
_diffrn_orient_matrix_UB_32      -0.0976721000
_diffrn_orient_matrix_UB_33      0.0826706000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0208
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            6999
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.316
_diffrn_reflns_theta_min         3.629
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.994
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80529
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light pink'
_exptl_crystal_density_diffrn    1.567
_exptl_crystal_description       plate
_exptl_crystal_F_000             508
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: dichloromethane, hexane'
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.526
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         3965
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0459
_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^)+(0.0684P)^2^+0.4167P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1222
_refine_ls_wR_factor_ref         0.1269
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3554
_reflns_number_total             3965
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc03691a2.cif
_cod_data_source_block           20180911dy-655-430
_cod_database_code               1552180
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_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 Ternary CH refined with riding coordinates:
 C10(H10)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), N6(H6), C14(H14), C25(H25), C26(H26)
2.c Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C), C29(H29A,H29B,H29C), C1(H1A,H1B,H1C)
;
_shelx_res_checksum              3446
_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 1.294
_oxdiff_exptl_absorpt_empirical_full_min 0.768