C-H Bond Alkylation of Cyclic Amides with Maleimides via a Site-Selective-Determining Six-Membered Ruthenacycle.
Yuan, Yu-Chao; Goujon, Marion; Bruneau, Christian; Roisnel, Thierry; Gramage-Doria, Rafael; The Journal of organic chemistry  (2019) –; doi:10.1021/acs.joc.9b02690

data_4037626
_publ_section_title
;
 C-H Bond Alkylation of Cyclic Amides with Maleimides via a
 Site-Selective-Determining Six-Membered Ruthenacycle.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b02690
_journal_year                    2019
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C24 H18 N2 O3'
_chemical_formula_sum            'C24 H18 N2 O3'
_chemical_formula_weight         382.40
_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     dual
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 119.990(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.8305(12)
_cell_length_b                   9.6000(9)
_cell_length_c                   17.8131(16)
_cell_measurement_reflns_used    9900
_cell_measurement_temperature    150
_cell_measurement_theta_max      27.4968
_cell_measurement_theta_min      2.4988
_cell_measurement_wavelength     0.71073
_cell_volume                     1900.3(3)
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_collection       'SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_molecular_graphics
'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2016)'
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2019)'
_computing_structure_refinement  'SHELXL-2018_3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT (G. Sheldrick, 2015)'
_diffrn_ambient_temperature      150
_diffrn_detector                 '(CMOS) PHOTON 100'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_orient_matrix_UB_11      0.0469363
_diffrn_orient_matrix_UB_12      -0.0863133
_diffrn_orient_matrix_UB_13      0.0283152
_diffrn_orient_matrix_UB_21      0.0574198
_diffrn_orient_matrix_UB_22      0.0229799
_diffrn_orient_matrix_UB_23      -0.0207393
_diffrn_orient_matrix_UB_31      0.0509680
_diffrn_orient_matrix_UB_32      0.0535967
_diffrn_orient_matrix_UB_33      0.0544915
_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  0.0572
_diffrn_reflns_av_unetI/netI     0.0551
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            15488
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.497
_diffrn_reflns_theta_min         2.499
_diffrn_source_current           1.0
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_correction_T_min  0.694
_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    1.337
_exptl_crystal_description       prism
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.436
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.147
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         4311
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.147
_refine_ls_R_factor_all          0.1010
_refine_ls_R_factor_gt           0.0872
_refine_ls_shift/su_max          0.013
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0908P)^2^+2.6776P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2320
_refine_ls_wR_factor_ref         0.2434
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3514
_reflns_number_total             4311
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo9b02690_si_002.cif
_cod_data_source_block           MG30
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4037626
_shelx_res_checksum              3468
_shelx_hkl_checksum              1941