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_4518082
_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         'C30 H36 N4 O Si'
_chemical_formula_sum            'C30 H36 N4 O Si'
_chemical_formula_weight         496.72
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2020-06-24
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                101.8688(9)
_cell_angle_beta                 102.9380(10)
_cell_angle_gamma                99.0470(8)
_cell_formula_units_Z            6
_cell_length_a                   11.2966(3)
_cell_length_b                   17.3143(4)
_cell_length_c                   23.2024(5)
_cell_measurement_reflns_used    9331
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      79.72
_cell_measurement_theta_min      2.67
_cell_volume                     4228.98(18)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 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      100.0
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.965
_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  0.0775
_diffrn_reflns_av_unetI/netI     0.0605
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            78536
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         80.083
_diffrn_reflns_theta_min         2.018
_diffrn_source                   'INCOATEC Imus micro-focus source'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.949
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8004
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0993 before and 0.0799 after correction.
The Ratio of minimum to maximum transmission is 0.8004.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.170
_exptl_crystal_description       block
_exptl_crystal_F_000             1596
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.413
_refine_diff_density_min         -0.547
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     994
_refine_ls_number_reflns         17834
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0824
_refine_ls_R_factor_gt           0.0571
_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^)+(0.0841P)^2^+1.1794P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1521
_refine_ls_wR_factor_ref         0.1745
_reflns_Friedel_coverage         0.000
_reflns_number_gt                12546
_reflns_number_total             17834
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs0c03207_si_004.cif
_cod_data_source_block           155
_cod_database_code               4518082
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.911
_shelx_estimated_absorpt_t_min   0.848
_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.a Ternary CH refined with riding coordinates:
 C28(H28), C31(H31), C34(H34), C68(H68), C71(H71), C74(H74), C108(H108),
 C111(H111), C114(H114)
2.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C58(H58A,H58B), C98(H98A,H98B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C11(H11), C15(H15), C20(H20), C21(H21), C22(H22),
 C23(H23), C24(H24), C41(H41), C42(H42), C43(H43), C51(H51), C55(H55), C60(H60),
  C61(H61), C62(H62), C63(H63), C64(H64), C81(H81), C82(H82), C83(H83),
 C91(H91), C95(H95), C100(H100), C101(H101), C102(H102), C103(H103), C104(H104)
2.d Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C29(H29A,H29B,H29C), C30(H30A,H30B,H30C), C32(H32A,H32B,
 H32C), C33(H33A,H33B,H33C), C35(H35A,H35B,H35C), C36(H36A,H36B,H36C), C46(H46A,
 H46B,H46C), C69(H69A,H69B,H69C), C70(H70A,H70B,H70C), C72(H72A,H72B,H72C),
 C73(H73A,H73B,H73C), C75(H75A,H75B,H75C), C76(H76A,H76B,H76C), C86(H86A,H86B,
 H86C), C109(H10A,H10B,H10C), C110(H11A,H11B,H11C), C112(H11D,H11E,H11F),
 C113(H11G,H11H,H11I), C115(H11J,H11K,H11L), C116(H11M,H11N,H11O)
;
_shelx_res_checksum              5944
_shelx_hkl_checksum              87842
_olex2_submission_special_instructions 'No special instructions were received'