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_1552181
_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 H16 F3 N2 O8 S2, H2 O'
_chemical_formula_sum            'C17 H18 F3 N2 O9 S2'
_chemical_formula_weight         515.45
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2018-10-18
_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                85.869(4)
_cell_angle_beta                 72.343(4)
_cell_angle_gamma                71.018(4)
_cell_formula_units_Z            2
_cell_length_a                   9.3787(4)
_cell_length_b                   10.6208(5)
_cell_length_c                   11.4671(6)
_cell_measurement_reflns_used    3388
_cell_measurement_temperature    109.5(5)
_cell_measurement_theta_max      70.8420
_cell_measurement_theta_min      4.0350
_cell_volume                     1028.78(9)
_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      N~2~
_diffrn_ambient_temperature      109.5(5)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2137
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.964
_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   -114.00 -33.00   1.00    1.00    --  -40.81 -38.00  90.00   81
  2  \w   -107.00  -8.00   1.00    1.00    --  -40.81 -77.00-150.00   99
  3  \w    -87.00  -2.00   1.00    1.00    --  -40.81 125.00 -30.00   85
  4  \w      2.00  50.00   1.00    1.00    --   40.81 -99.00 -30.00   48
  5  \w    136.00 174.00   1.00    1.00    --  100.91  45.00   0.00   38
  6  \w     29.00 117.00   1.00    1.00    --  100.91-125.00 150.00   88
  7  \w    122.00 154.00   1.00    1.00    --  100.91  45.00 -90.00   32
  8  \w    110.00 137.00   1.00    1.00    --  100.91 125.00-180.00   27
  9  \w     77.00 120.00   1.00    1.00    --  100.91  45.00   0.00   43
 10  \w     79.00 108.00   1.00    1.00    --  100.91 -95.00-180.00   29
 11  \w     74.00 163.00   1.00    1.00    --  100.91  77.00 120.00   89
 12  \w     73.00 177.00   1.00    1.00    --  100.91  30.00  60.00  104
 13  \w     87.00 113.00   1.00    1.00    --  100.91-125.00 -30.00   26
 14  \w     30.00  97.00   1.00    1.00    --  100.91 -61.00-150.00   67
 15  \w    100.00 169.00   1.00    1.00    --  100.91 125.00 -60.00   69
 16  \w     25.00 133.00   1.00    1.00    --  100.91 -77.00 -60.00  108
;
_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      -0.0062742000
_diffrn_orient_matrix_UB_12      -0.1194132000
_diffrn_orient_matrix_UB_13      0.0837650000
_diffrn_orient_matrix_UB_21      -0.1800110000
_diffrn_orient_matrix_UB_22      0.0638583000
_diffrn_orient_matrix_UB_23      0.0535019000
_diffrn_orient_matrix_UB_31      -0.0254036000
_diffrn_orient_matrix_UB_32      -0.0721993000
_diffrn_orient_matrix_UB_33      -0.1000800000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_unetI/netI     0.0406
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6843
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.269
_diffrn_reflns_theta_min         4.047
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.121
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81854
_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 colourless'
_exptl_crystal_density_diffrn    1.664
_exptl_crystal_description       plate
_exptl_crystal_F_000             530
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.454
_refine_diff_density_min         -0.704
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     304
_refine_ls_number_reflns         3854
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0523
_refine_ls_R_factor_gt           0.0449
_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^)+(0.0626P)^2^+1.2049P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1186
_refine_ls_wR_factor_ref         0.1260
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3346
_reflns_number_total             3854
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc03691a2.cif
_cod_data_source_block           20181015dongyi
_cod_original_cell_volume        1028.77(9)
_cod_database_code               1552181
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.97
_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, All O(H,H) groups
2. Restrained distances
 H1B-H13
 2.45 with sigma of 0.01
3.a Free rotating group:
 O1(H1A,H1B)
3.b Ternary CH refined with riding coordinates:
 C25(H25)
3.c Aromatic/amide H refined with riding coordinates:
 N11(H11), N13(H13), C14(H14), C15(H15), C23(H23), C29(H29)
3.d Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C30(H30A,H30B,H30C)
;
_shelx_res_checksum              58976
_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 1.327
_oxdiff_exptl_absorpt_empirical_full_min 0.761