Site-selective Ru-catalyzed C-H bond alkenylation with biologically relevant isoindolinones: a case of catalyst performance controlled by subtle stereo-electronic effects of the weak directing group
Yuan, Yu-Chao; Bruneau, Christian; Roisnel, Thierry; Gramage-Doria, Rafael; Catalysis Science & Technology  (2019) –; doi:10.1039/C9CY01231A

data_1552140
_publ_section_title
;
 Site-selective Ru-catalyzed C-H bond alkenylation with biologically
 relevant isoindolinones: a case of catalyst performance controlled by
 subtle stereo-electronic effects of the weak directing group
;
_journal_name_full               'Catalysis Science &amp; Technology'
_journal_paper_doi               10.1039/C9CY01231A
_journal_year                    2019
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C22 H17 N O'
_chemical_formula_sum            'C22 H17 N O'
_chemical_formula_weight         311.36
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2018-11-20
_audit_creation_method           'SHELXL-2018_3, CRYSCALC (Oct. 2018)'
_audit_update_record
;
2019-02-06 deposited with the CCDC.    2019-08-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.658(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.0929(7)
_cell_length_b                   16.8891(17)
_cell_length_c                   15.9338(19)
_cell_measurement_reflns_used    7683
_cell_measurement_temperature    150
_cell_measurement_theta_max      27.4971
_cell_measurement_theta_min      2.5576
_cell_measurement_wavelength     0.71073
_cell_volume                     1639.0(3)
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_collection       'SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_molecular_graphics    'SXGRAPH (Farrugia, 1999), Mercury (CSD, 2016)'
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2018)'
_computing_structure_refinement  'SHELXL-2018_3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150
_diffrn_detector                 '(CMOS) PHOTON 100'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12524
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.570
_diffrn_reflns_theta_min         2.412
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_correction_T_min  0.807
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_description       stick
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.0173(18)
_refine_ls_extinction_method     'SHELXL-2018_3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3755
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0579
_refine_ls_R_factor_gt           0.0450
_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^)+(0.0433P)^2^+0.6999P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1109
_refine_ls_wR_factor_ref         0.1180
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3067
_reflns_number_total             3755
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c9cy01231a2.cif
_cod_data_source_block           YYC435
_cod_database_code               1552140
_shelx_res_checksum              85133