N-Alkylation and N,C-Dialkylation of Amines with Alcohols in the Presence of Ruthenium Catalysts with Chelating N-Heterocyclic Carbene Ligands
Şahin, Zeynel; Gürbüz, Nevin; Özdemir, İsmail; Şahin, Onur; Büyükgüngör, Orhan; Achard, Mathieu; Bruneau, Christian; Organometallics 34 (2015) 2296–; doi:10.1021/om501066n

data_4085678
_publ_section_title
;
 N-Alkylation and N,C-Dialkylation of Amines with Alcohols in the Presence
 of Ruthenium Catalysts with Chelating N-Heterocyclic Carbene Ligands
;
_journal_issue                   11
_journal_name_full               Organometallics
_journal_page_first              2296
_journal_paper_doi               10.1021/om501066n
_journal_volume                  34
_journal_year                    2015
_chemical_formula_moiety         'C22 H27 Br2 N2 O2 Ru, C H Cl3'
_chemical_formula_sum            'C23 H28 Br2 Cl3 N2 O2 Ru'
_chemical_formula_weight         731.71
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 108.536(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.3080(7)
_cell_length_b                   10.4183(8)
_cell_length_c                   20.6079(11)
_cell_measurement_reflns_used    12988
_cell_measurement_temperature    296
_cell_measurement_theta_max      27.87
_cell_measurement_theta_min      1.61
_cell_volume                     2709.0(3)
_computing_cell_refinement       'X-AREA (Stoe & Cie, 2002)'
_computing_data_collection       'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction        'X-RED (Stoe & Cie, 2002)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       'w scan rotation'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1137
_diffrn_reflns_av_sigmaI/netI    0.1259
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            20454
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.61
_diffrn_standards_decay_%        <2
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.848
_exptl_absorpt_correction_T_max  0.9247
_exptl_absorpt_correction_T_min  0.4035
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(X-RED32; Stoe & Cie, 2002)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.794
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1444
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.999
_refine_diff_density_min         -1.287
_refine_diff_density_rms         0.169
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.925
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     297
_refine_ls_number_reflns         4780
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      0.928
_refine_ls_R_factor_all          0.1286
_refine_ls_R_factor_gt           0.0721
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1020P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1725
_refine_ls_wR_factor_ref         0.1947
_reflns_number_gt                2574
_reflns_number_total             4780
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            om501066n_si_002.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 4085678--4085679.cif.'
_cod_original_sg_symbol_Hall     -P2ybc
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               4085678