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_4518081
_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         'C23 H26 Ir N O2, 0.69(H2 O1)'
_chemical_formula_sum            'C23 H27.38 Ir N O2.69'
_chemical_formula_weight         553.08
_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   mixed
_audit_creation_date             2020-01-07
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                88.8330(10)
_cell_angle_beta                 86.1300(10)
_cell_angle_gamma                88.8850(10)
_cell_formula_units_Z            2
_cell_length_a                   8.2522(3)
_cell_length_b                   10.6947(5)
_cell_length_c                   11.6450(5)
_cell_measurement_reflns_used    9840
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.36
_cell_measurement_theta_min      3.81
_cell_volume                     1025.00(7)
_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      100.03
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.984
_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  0.0304
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            17078
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.373
_diffrn_reflns_theta_min         3.805
_diffrn_source                   'INCOATEC Imus micro-focus source'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    12.776
_exptl_absorpt_correction_T_max  0.5006
_exptl_absorpt_correction_T_min  0.3033
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1057 before and 0.0463 after correction.
The Ratio of minimum to maximum transmission is 0.6059.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.792
_exptl_crystal_description       rod
_exptl_crystal_F_000             542
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         1.132
_refine_diff_density_min         -1.070
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         4001
_refine_ls_number_restraints     14
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0180
_refine_ls_R_factor_gt           0.0179
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0159P)^2^+1.1127P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0435
_refine_ls_wR_factor_ref         0.0436
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3977
_reflns_number_total             4001
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs0c03207_si_002.cif
_cod_data_source_block           ms_yxh_12_40_1_0m
_cod_database_code               4518081
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.629
_shelx_estimated_absorpt_t_min   0.287
_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, All O(H) groups
2. Restrained distances
 O1S-H1SA = O1S-H1SB
 0.87 with sigma of 0.02
 H1SA-H1SB
 1.39 with sigma of 0.04
 H1SA-O1
 1.9 with sigma of 0.04
 Ir1-O1 \\sim Ir1-O1B
 with sigma of 0.02
 O1B-C2B \\sim O1-C2
 with sigma of 0.02
 O3-C2 \\sim O3B-C2B
 with sigma of 0.02
 C4B-C2B \\sim C4-C2
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C4B \\sim C4: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
Uanis(O1B) = Uanis(O1)
4. Others
 Sof(O1B)=Sof(O3B)=Sof(C2B)=Sof(C4B)=Sof(H4BA)=Sof(H4BB)=Sof(H4BC)=1-FVAR(1)
 Sof(O3)=Sof(C2)=Sof(C4)=Sof(H4A)=Sof(H4B)=Sof(H4C)=Sof(O1S)=Sof(O1)=Sof(H1SA)=
 Sof(H1SB)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C15(H15), C9(H9), C12(H12), C6(H6), C14(H14), C13(H13), C7(H7), C8(H8)
5.b Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C25(H25A,H25B,
 H25C), C26(H26A,H26B,H26C), C4(H4A,H4B,H4C), C4B(H4BA,H4BB,H4BC)
;
_shelx_res_checksum              2225
_shelx_hkl_checksum              40005
_olex2_submission_special_instructions 'No special instructions were received'