Facilitating Ir-Catalyzed C‒H Alkynylation with Electrochemistry: Anodic Oxidation-Induced Reductive Elimination
Ye, Xiaohan; Wang, Chenhuan; Zhang, Shuyao; Wei, Jingwen; Shan, Chuan; Wojtas, Lukasz; Xie, Yan; Shi, Xiaodong; ACS Catalysis  (2020) 11693–11699; doi:10.1021/acscatal.0c03207

data_4518083
_publ_section_title
;
 Facilitating Ir-Catalyzed C--H Alkynylation with Electrochemistry: Anodic
 Oxidation-Induced Reductive Elimination
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              11693
_journal_page_last               11699
_journal_paper_doi               10.1021/acscatal.0c03207
_journal_year                    2020
_chemical_formula_moiety         'C32 H44 Ir N Si'
_chemical_formula_sum            'C32 H44 Ir N Si'
_chemical_formula_weight         662.97
_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
_audit_creation_date             2020-01-09
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 103.0170(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.3222(3)
_cell_length_b                   18.4507(5)
_cell_length_c                   14.6046(4)
_cell_measurement_reflns_used    9442
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.36
_cell_measurement_theta_min      3.92
_cell_volume                     2972.54(14)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.01
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON II CPAD'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            35441
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.348
_diffrn_reflns_theta_min         3.923
_diffrn_source                   'INCOATEC Imus micro-focus source'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    9.211
_exptl_absorpt_correction_T_max  0.6005
_exptl_absorpt_correction_T_min  0.4445
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0870 before and 0.0505 after correction.
The Ratio of minimum to maximum transmission is 0.7402.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.481
_exptl_crystal_description       needle
_exptl_crystal_F_000             1336
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.315
_refine_diff_density_min         -0.449
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         5821
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.101
_refine_ls_R_factor_all          0.0172
_refine_ls_R_factor_gt           0.0165
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0116P)^2^+1.8028P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0378
_refine_ls_wR_factor_ref         0.0382
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5670
_reflns_number_total             5821
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs0c03207_si_003.cif
_cod_data_source_block           yxh_12_40_2
_cod_database_code               4518083
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.710
_shelx_estimated_absorpt_t_min   0.404
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Shared sites
{C29, N29}
{N22, C22}
3. Uiso/Uaniso restraints and constraints
Uanis(C29) = Uanis(N29)
Uanis(N22) = Uanis(C22)
4. Others
 Sof(C22)=Sof(H23A)=Sof(N29)=Sof(H30A)=1-FVAR(1)
 Sof(N22)=Sof(H23)=Sof(C29)=Sof(H30)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C3(H3), C6(H6), C9(H9)
5.b Aromatic/amide H refined with riding coordinates:
 C23(H23), C23(H23A), C24(H24), C25(H25), C26(H26), C30(H30), C30(H30A),
 C31(H31), C32(H32), C33(H33)
5.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C5(H5A,H5B,H5C), C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C10(H10A,
 H10B,H10C), C11(H11A,H11B,H11C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C),
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C)
;
_shelx_res_checksum              70579
_shelx_hkl_checksum              87258
_olex2_submission_special_instructions 'No special instructions were received'