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_4518087
_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         'C33 H48 F N Si2'
_chemical_formula_sum            'C33 H48 F N Si2'
_chemical_formula_weight         533.90
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2020-06-27
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 96.5480(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.0636(2)
_cell_length_b                   13.0350(4)
_cell_length_c                   15.6853(5)
_cell_measurement_reflns_used    9744
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      79.61
_cell_measurement_theta_min      2.84
_cell_volume                     1637.91(8)
_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 0.993
_diffrn_measured_fraction_theta_max 0.968
_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  0.0640
_diffrn_reflns_av_unetI/netI     0.0561
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            24112
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.936
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         79.719
_diffrn_reflns_theta_min         2.836
_diffrn_source                   'INCOATEC Imus micro-focus source'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.173
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7676
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1274 before and 0.0865 after correction.
The Ratio of minimum to maximum transmission is 0.7676.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.083
_exptl_crystal_description       plate
_exptl_crystal_F_000             580
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Flack x determined using 2649 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.064(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     377
_refine_ls_number_reflns         6683
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_gt           0.0465
_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^)+(0.0722P)^2^+0.2120P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1237
_refine_ls_wR_factor_ref         0.1312
_reflns_Friedel_coverage         0.851
_reflns_Friedel_fraction_full    0.967
_reflns_Friedel_fraction_max     0.901
_reflns_number_gt                6235
_reflns_number_total             6683
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs0c03207_si_005.cif
_cod_data_source_block           ms_yxh_163_3_0m
_cod_database_code               4518087
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.944
_shelx_estimated_absorpt_t_min   0.735
_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, All C(H,H,H,H,H,H) groups
2. Restrained distances
 C34A-C32 = C34B-C32
 1.52 with sigma of 0.02
 C18B-C17B = C19-C17B
 1.52 with sigma of 0.02
 C18B-Si2
 2.86 with sigma of 0.04
 Si2-C17B \\sim Si2-C17A
 with sigma of 0.01
3. Others
 Sof(H32A)=Sof(C34B)=Sof(H34D)=Sof(H34E)=Sof(H34F)=1-FVAR(1)
 Sof(H32)=Sof(C34A)=Sof(H34A)=Sof(H34B)=Sof(H34C)=FVAR(1)
 Sof(C17B)=Sof(H17B)=Sof(C18B)=Sof(H18D)=Sof(H18E)=Sof(H18F)=Sof(H19D)=
 Sof(H19E)=Sof(H19F)=1-FVAR(2)
 Sof(C17A)=Sof(H17A)=Sof(C18A)=Sof(H18A)=Sof(H18B)=Sof(H18C)=Sof(H19A)=
 Sof(H19B)=Sof(H19C)=FVAR(2)
 Sof(H2)=Sof(F2)=1-FVAR(3)
 Sof(F1)=Sof(H6)=FVAR(3)
4.a Ternary CH refined with riding coordinates:
 C17A(H17A), C17B(H17B), C20(H20), C23(H23), C26(H26), C29(H29), C32(H32),
 C32(H32A)
4.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C6(H6), C13(H13), C14(H14), C15(H15), C16(H16)
4.c Idealised Me refined as rotating group:
 C18A(H18A,H18B,H18C), C18B(H18D,H18E,H18F), C19(H19A,H19B,H19C), C19(H19D,
 H19E,H19F), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C24(H24A,H24B,H24C),
 C25(H25A,H25B,H25C), C27(H27A,H27B,H27C), C28(H28A,H28B,H28C), C30(H30A,H30B,
 H30C), C31(H31A,H31B,H31C), C33(H33A,H33B,H33C), C34A(H34A,H34B,H34C),
 C34B(H34D,H34E,H34F)
;
_shelx_res_checksum              87804
_shelx_hkl_checksum              21244
_olex2_submission_special_instructions 'No special instructions were received'