Three-Component Ruthenium-Catalyzed Direct <i>Meta-</i>Selective C-H Activation of Arenes: A New Approach to the Alkylarylation of Alkenes.
Wang, Xin-Gang; Li, Yuke; Liu, Hong-Chao; Zhang, Bo-Sheng; Gou, Xue-Ya; Wang, Qiang; Ma, Jun-Wei; Liang, Yong-Min; Journal of the American Chemical Society 141 (2019) 13914–13922; doi:10.1021/jacs.9b06608

data_4128876
_publ_section_title
;
 Three-Component Ruthenium-Catalyzed Direct <i>Meta-</i>Selective C-H
 Activation of Arenes: A New Approach to the Alkylarylation of Alkenes.
;
_journal_issue                   35
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13914
_journal_page_last               13922
_journal_paper_doi               10.1021/jacs.9b06608
_journal_volume                  141
_journal_year                    2019
_chemical_formula_moiety         'C23.25 H20.5 F2 N2 O5'
_chemical_formula_sum            'C23.25 H20.5 F2 N2 O5'
_chemical_formula_weight         445.92
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-05-20
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 96.031(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.9425(12)
_cell_length_b                   8.5046(8)
_cell_length_c                   19.818(2)
_cell_measurement_reflns_used    884
_cell_measurement_temperature    292.90(10)
_cell_measurement_theta_max      21.0130
_cell_measurement_theta_min      3.9670
_cell_volume                     2169.3(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      292.90(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega   14.00   51.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.4273   77.0000   30.0000 37

  2 omega   32.00   58.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   77.0000  120.0000 26

  3 omega    4.00   94.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   77.0000  -90.0000 90

  4 omega   14.00   81.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   77.0000 -180.0000 67
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0049876000
_diffrn_orient_matrix_UB_12      0.0171918000
_diffrn_orient_matrix_UB_13      -0.0352569000
_diffrn_orient_matrix_UB_21      -0.0514929000
_diffrn_orient_matrix_UB_22      -0.0297433000
_diffrn_orient_matrix_UB_23      -0.0031081000
_diffrn_orient_matrix_UB_31      -0.0189966000
_diffrn_orient_matrix_UB_32      0.0759169000
_diffrn_orient_matrix_UB_33      0.0066876000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0453
_diffrn_reflns_av_unetI/netI     0.1024
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            7536
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.017
_diffrn_reflns_theta_min         3.440
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53106
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_description       block
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.443
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         4266
_refine_ls_number_restraints     13
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.2073
_refine_ls_R_factor_gt           0.0861
_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^)+(0.0750P)^2^+0.4233P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1870
_refine_ls_wR_factor_ref         0.2538
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1585
_reflns_number_total             4266
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b06608_si_002.cif
_cod_data_source_block           wangxg_0509
_cod_original_cell_volume        2169.4(4)
_cod_original_formula_sum        'C23.25 H20.50 F2 N2 O5'
_cod_database_code               4128876
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.52
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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. Restrained distances
 O3-C23B
 1.5 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C23) \\sim Ueq, Uanis(C23B) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
4. Others
 Fixed Sof: C23B(0.25) H23A(0.25) H23B(0.25) C24B(0.25) H24A(0.25) H24B(0.25)
 H24C(0.25) C23(0.75) H23C(0.75) H23D(0.75) H23E(0.75)
5.a Ternary CH refined with riding coordinates:
 C13(H13)
5.b Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C23B(H23A,H23B)
5.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11), C15(H15),
 C16(H16), C18(H18), C19(H19)
5.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C24B(H24A,H24B,H24C), C23(H23C,H23D,H23E)
;
_shelx_res_checksum              85992
_shelx_hkl_checksum              82532
_olex2_date_sample_data_collection 2019-05-09
_olex2_submission_special_instructions 'No special instructions were received'