RhCl3-Catalyzed Oxidative C‒H/C‒H Cross-Coupling of (Hetero)aromatic Sulfonamides with (Hetero)arenes
Ran, You; Yang, Yudong; You, Huansha; You, Jingsong; ACS Catalysis 8 (2018) 1796–; doi:10.1021/acscatal.7b04298

data_4514384
_publ_section_title
;
 RhCl3-Catalyzed Oxidative C--H/C--H Cross-Coupling of (Hetero)aromatic
 Sulfonamides with (Hetero)arenes
;
_journal_issue                   3
_journal_name_full               'ACS Catalysis'
_journal_page_first              1796
_journal_paper_doi               10.1021/acscatal.7b04298
_journal_volume                  8
_journal_year                    2018
_chemical_formula_moiety         'C24 H29 N2 O3 Rh S'
_chemical_formula_sum            'C24 H29 N2 O3 Rh S'
_chemical_formula_weight         528.46
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-01-12
_audit_creation_method
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Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 90.736(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.8164(3)
_cell_length_b                   14.3580(4)
_cell_length_c                   17.0526(4)
_cell_measurement_reflns_used    4171
_cell_measurement_temperature    293.06(10)
_cell_measurement_theta_max      72.3480
_cell_measurement_theta_min      4.0400
_cell_volume                     2403.26(11)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.06(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measurement_details
;
  1 omega   20.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000 -180.0000 84

  2 omega  -31.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -77.0000   30.0000 94

  3 omega   44.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921 -162.0000 -136.0000 65

  4 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -57.0000 -120.0000 84

  5 omega   38.00   91.00   1.0000    2.3700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   60.0000 53

  6 omega   40.00   98.00   1.0000    2.3700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -150.0000 58

  7 omega   39.00  109.00   1.0000    2.3700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -30.0000 70

  8 omega   40.00   88.00   1.0000    2.3700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  150.0000 48

  9 omega   55.00   91.00   1.0000    2.3700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   90.0000 36

 10 omega   40.00   97.00   1.0000    2.3700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -90.0000 57

 11 omega   43.00   89.00   1.0000    2.3700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  150.0000 46

 12 omega   37.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.6671   77.0000   30.0000 61

 13 omega   65.00  100.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.6671   57.0000  120.0000 35

 14 omega   96.00  153.00   1.0000    2.3700
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -90.0000 57

 15 omega   61.00   87.00   1.0000    2.3700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -120.0000 26

 16 omega   64.00   95.00   1.0000    2.3700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -150.0000 31

 17 omega   42.00   52.00   1.0000    2.3700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -60.0000 10
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.1293198000
_diffrn_orient_matrix_UB_12      0.0212695000
_diffrn_orient_matrix_UB_13      0.0471544000
_diffrn_orient_matrix_UB_21      0.0863239000
_diffrn_orient_matrix_UB_22      0.0043994000
_diffrn_orient_matrix_UB_23      0.0760414000
_diffrn_orient_matrix_UB_31      0.0224124000
_diffrn_orient_matrix_UB_32      0.1049475000
_diffrn_orient_matrix_UB_33      -0.0127083000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_av_unetI/netI     0.0441
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            9899
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.487
_diffrn_reflns_theta_min         5.170
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    6.775
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.24044
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear dark red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.461
_exptl_crystal_description       block
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_refine_diff_density_max         1.144
_refine_diff_density_min         -0.912
_refine_diff_density_rms         0.144
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     287
_refine_ls_number_reflns         4540
_refine_ls_number_restraints     492
_refine_ls_restrained_S_all      1.144
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0588
_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^)+(0.1185P)^2^+2.0493P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1633
_refine_ls_wR_factor_ref         0.1738
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3982
_reflns_number_total             4540
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs7b04298_si_002.cif
_cod_data_source_block           yjs-ry-dw82-1
_cod_depositor_comments          'Adding full bibliography for 4514384.cif.'
_cod_database_code               4514384
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 97.62
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
C007 \\sim C009 \\sim C00A \\sim C00B \\sim C00C \\sim C00D \\sim C00E \\sim
C00F \\sim C00G \\sim C00H \\sim C00I \\sim C00J \\sim C00K \\sim C00L \\sim
C00M \\sim C00N \\sim C00O \\sim C00P \\sim C00Q \\sim C00R \\sim C00S \\sim
C00T \\sim C00U \\sim C00V: within 3.8A with sigma of 0.01 and sigma for
terminal atoms of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00D(H00D), C00H(H00H), C00I(H00I), C00J(H00J), C00K(H00K),
 C00L(H00L), C00M(H00M)
3.b Idealised Me refined as rotating group:
 C00G(H00B,H00C,H00E), C00Q(H00F,H00G,H00N), C00R(H00O,H00P,H00Q), C00S(H00R,
 H00S,H00T), C00T(H00U,H00V,H00W), C00U(H00X,H00Y,H), C00V(H00Z,HA,HB)
;
_olex2_submission_special_instructions 'No special instructions were received'