Iridium-Catalyzed Oxidative Heteroarylation of Arenes and Alkenes: Overcoming the Restriction to Specific Substrates
Tan, Guangying; You, Qiulin; You, Jingsong; ACS Catalysis 8 (2018) 8709–; doi:10.1021/acscatal.8b02639

data_4515711
_publ_section_title
;
 Iridium-Catalyzed Oxidative Heteroarylation of Arenes and Alkenes:
 Overcoming the Restriction to Specific Substrates
;
_journal_issue                   9
_journal_name_full               'ACS Catalysis'
_journal_page_first              8709
_journal_paper_doi               10.1021/acscatal.8b02639
_journal_volume                  8
_journal_year                    2018
_chemical_formula_moiety         '2(C16 H19 N O S)'
_chemical_formula_sum            'C32 H38 N2 O2 S2'
_chemical_formula_weight         546.76
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-06-06
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.03 svn.r3497 for OlexSys, GUI svn.r5486)
;
_cell_angle_alpha                90
_cell_angle_beta                 103.091(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.5365(3)
_cell_length_b                   14.4554(4)
_cell_length_c                   17.4788(4)
_cell_measurement_reflns_used    4874
_cell_measurement_temperature    294.05(10)
_cell_measurement_theta_max      72.3930
_cell_measurement_theta_min      3.9940
_cell_volume                     3085.19(14)
_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
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
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)'
_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      294.05(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega   23.00   90.00   1.0000    6.6200
omega____ theta____ kappa____ phi______ frames
    -       36.2921 -125.0000   30.0000 67

  2 omega  -31.00   63.00   1.0000    6.6200
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -77.0000  -30.0000 94

  3 omega   20.00  104.00   1.0000    6.6200
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000   60.0000 84

  4 omega   20.00  104.00   1.0000    6.6200
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000    0.0000 84

  5 omega  -31.00   63.00   1.0000    6.6200
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -77.0000 -150.0000 94

  6 omega   10.00  104.00   1.0000    6.6200
omega____ theta____ kappa____ phi______ frames
    -       36.2921   77.0000  120.0000 94

  7 omega  -35.00   66.00   1.0000    6.6200
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -19.0000 -150.0000 101

  8 omega   38.00   91.00   1.0000   26.4750
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000    0.0000 53

  9 omega   38.00   91.00   1.0000   26.4750
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   90.0000 53

 10 omega   87.00  178.00   1.0000   26.4750
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000 -150.0000 91

 11 omega   38.00   91.00   1.0000   26.4750
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  150.0000 53

 12 omega   38.00   91.00   1.0000   26.4750
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -30.0000 53

 13 omega   38.00  116.00   1.0000   26.4750
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  120.0000 78

 14 omega   91.00  173.00   1.0000   26.4750
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000   60.0000 82

 15 omega   72.00  107.00   1.0000   26.4750
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -150.0000 35

 16 omega   41.00   90.00   1.0000   26.4750
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -150.0000 49

 17 omega   42.00   68.00   1.0000   26.4750
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -90.0000 26

 18 omega   49.00  126.00   1.0000   26.4750
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000  -90.0000 77
;
_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      0.0084163000
_diffrn_orient_matrix_UB_12      0.1051749000
_diffrn_orient_matrix_UB_13      -0.0115069000
_diffrn_orient_matrix_UB_21      0.0972311000
_diffrn_orient_matrix_UB_22      -0.0152769000
_diffrn_orient_matrix_UB_23      -0.0389244000
_diffrn_orient_matrix_UB_31      -0.0800070000
_diffrn_orient_matrix_UB_32      -0.0076460000
_diffrn_orient_matrix_UB_33      -0.0808753000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            16182
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        65.077
_diffrn_reflns_theta_max         65.077
_diffrn_reflns_theta_min         4.912
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.789
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63385
_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 light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.177
_exptl_crystal_description       needle
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.75
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.271
_refine_diff_density_min         -0.453
_refine_diff_density_rms         0.101
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.438
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     351
_refine_ls_number_reflns         5242
_refine_ls_number_restraints     21
_refine_ls_restrained_S_all      1.445
_refine_ls_R_factor_all          0.1174
_refine_ls_R_factor_gt           0.1030
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3134
_refine_ls_wR_factor_ref         0.3425
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4139
_reflns_number_total             5242
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs8b02639_si_002.cif
_cod_data_source_block           tgy-1207
_cod_original_cell_volume        3085.18(14)
_cod_database_code               4515711
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.88
_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. Rigid bond restraints
 C00H
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C010, C011
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C008, C00G
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C1, C00H
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3. Uiso/Uaniso restraints and constraints
C00H: within 2A with sigma of 0.001 and sigma for terminal atoms of 0.002
C010 \\sim C011: within 2A with sigma of 0.001 and sigma for terminal atoms of
0.002
C008 \\sim C00G: within 2A with sigma of 0.001 and sigma for terminal atoms of
0.002
C1 \\sim C00H: within 2A with sigma of 0.001 and sigma for terminal atoms of
0.02
4.a Aromatic/amide H refined with riding coordinates:
 N005(H005), N006(H006), C008(H008), C009(H009), C00F(H00J), C00Q(H00Q),
 C00R(H00R), C00S(H00S), C00T(H00T), C00X(H00), C00Y(H00Y), C010(H010),
 C011(H011), C1(H1)
4.b Idealised Me refined as rotating group:
 C00N(H00A,H00B,H00C), C00O(H00K,H00L,H00M), C00P(H00N,H00O,H00P), C00U(H00U,
 H00V,H00W), C00V(H00X,H00Z,H), C00W(H00D,H00E,H00F), C00Z(H00G,H00H,H00I),
 C012(H01A,H01B,H01C)
;
_olex2_submission_special_instructions 'No special instructions were received'