Chemoselective Cross-Coupling between Two Different and Unactivated C(aryl)-O Bonds Enabled by Chromium Catalysis.
Tang, Jinghua; Liu, Liu Leo; Yang, Shangru; Cong, Xuefeng; Luo, Meiming; Zeng, Xiaoming; Journal of the American Chemical Society 142 (2020) 7715–7720; doi:10.1021/jacs.0c00283

data_4134758
_publ_section_title
;
 Chemoselective Cross-Coupling between Two Different and Unactivated
 C(aryl)-O Bonds Enabled by Chromium Catalysis.
;
_journal_issue                   17
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7715
_journal_page_last               7720
_journal_paper_doi               10.1021/jacs.0c00283
_journal_volume                  142
_journal_year                    2020
_chemical_formula_moiety         'C20 H20 O2 Si'
_chemical_formula_sum            'C20 H20 O2 Si'
_chemical_formula_weight         320.45
_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
_atom_sites_solution_primary     iterative
_audit_creation_date             2018-01-16
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                100.434(4)
_cell_angle_beta                 91.333(5)
_cell_angle_gamma                93.497(4)
_cell_formula_units_Z            2
_cell_length_a                   7.0319(4)
_cell_length_b                   8.2216(3)
_cell_length_c                   22.6065(12)
_cell_measurement_reflns_used    2378
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.9020
_cell_measurement_theta_min      3.4730
_cell_volume                     1282.17(11)
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega   14.00   78.00   0.8000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       16.6856   38.0000   30.0000 80

  2 omega  -24.00   18.40   0.8000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669  -99.0000  -30.0000 53

  3 omega   32.00   57.60   0.8000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       16.6856 -178.0000 -120.0000 32

  4 omega  -83.00   11.40   0.8000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669  -77.0000   90.0000 118

  5 omega  -42.00   49.20   0.8000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669   77.0000 -150.0000 114

  6 omega  -87.00  -35.80   0.8000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669 -178.0000 -180.0000 64
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0146480000
_diffrn_orient_matrix_UB_12      -0.0859500000
_diffrn_orient_matrix_UB_13      -0.0058133000
_diffrn_orient_matrix_UB_21      -0.0182307000
_diffrn_orient_matrix_UB_22      -0.0040844000
_diffrn_orient_matrix_UB_23      0.0304418000
_diffrn_orient_matrix_UB_31      -0.0983769000
_diffrn_orient_matrix_UB_32      -0.0180343000
_diffrn_orient_matrix_UB_33      -0.0076537000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0181
_diffrn_reflns_av_unetI/netI     0.0453
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            10231
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.368
_diffrn_reflns_theta_min         3.076
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77654
_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_density_diffrn    0.830
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description
;
;
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.138
_refine_diff_density_rms         0.026
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.978
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     216
_refine_ls_number_reflns         5231
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.978
_refine_ls_R_factor_all          0.0911
_refine_ls_R_factor_gt           0.0533
_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^)+(0.0687P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1321
_refine_ls_wR_factor_ref         0.1476
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2992
_reflns_number_total             5231
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja0c00283_si_002.cif
_cod_data_source_block           180116_s1_ll_2246
_cod_depositor_comments          'Adding full bibliography for 4134758.cif.'
_cod_original_cell_volume        1282.18(11)
_cod_database_code               4134758
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         c12h12n2o3cl1
_shelx_estimated_absorpt_t_max   0.976
_shelx_estimated_absorpt_t_min   0.967
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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,H,H,H) groups, All O(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(Si1) = Uanis(Si1A)
3. Others
 Sof(Si1A)=Sof(H20D)=Sof(H20E)=Sof(H20F)=Sof(H19D)=Sof(H19E)=Sof(H19F)=
 Sof(H18D)=Sof(H18E)=Sof(H18F)=1-FVAR(1)
 Sof(Si1)=Sof(H20A)=Sof(H20B)=Sof(H20C)=Sof(H19A)=Sof(H19B)=Sof(H19C)=
 Sof(H18A)=Sof(H18B)=Sof(H18C)=FVAR(1)
4.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C7(H7), C6(H6), C17(H17), C9(H9), C11(H11), C5(H5), C16(H16),
 C13(H13), C14(H14)
4.b Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C20(H20D,H20E,H20F), C19(H19A,H19B,H19C), C19(H19D,H19E,
 H19F), C18(H18A,H18B,H18C), C18(H18D,H18E,H18F)
4.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_olex2_submission_special_instructions 'No special instructions were received'
_platon_squeeze_void_probe_radius 1.20