N-Heterocyclic Carbene Based Ruthenium-Catalyzed Direct Amide Synthesis from Alcohols and Secondary Amines: Involvement of Esters
Cheng Chen; Yao Zhang; Soon Hyeok Hong; Journal of Organic Chemistry 76 (2011) 10005–10010; doi:10.1021/jo201756z

data_4026788
_publ_section_title
;
 N-Heterocyclic Carbene Based Ruthenium-Catalyzed Direct Amide Synthesis
 from Alcohols and Secondary Amines: Involvement of Esters
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              10005
_journal_page_last               10010
_journal_paper_doi               10.1021/jo201756z
_journal_volume                  76
_journal_year                    2011
_chemical_formula_moiety         'C15 H22 Cl2 N2 Ru, C H Cl3 '
_chemical_formula_sum            'C16 H23 Cl5 N2 Ru'
_chemical_formula_weight         521.68
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 95.8110(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.9375(3)
_cell_length_b                   15.2834(4)
_cell_length_c                   15.6299(5)
_cell_measurement_reflns_used    9137
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      33.23
_cell_measurement_theta_min      2.52
_cell_volume                     2124.00(11)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      103(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_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  0.0270
_diffrn_reflns_av_sigmaI/netI    0.0224
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            41142
_diffrn_reflns_theta_full        33.28
_diffrn_reflns_theta_max         33.28
_diffrn_reflns_theta_min         2.52
_exptl_absorpt_coefficient_mu    1.369
_exptl_absorpt_correction_T_max  0.7714
_exptl_absorpt_correction_T_min  0.6533
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.631
_exptl_crystal_description       block
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.20
_refine_diff_density_max         1.263
_refine_diff_density_min         -0.796
_refine_diff_density_rms         0.099
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         8152
_refine_ls_number_restraints     23
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0309
_refine_ls_R_factor_gt           0.0251
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0340P)^2^+1.3553P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0662
_refine_ls_wR_factor_ref         0.0691
_reflns_number_gt                7154
_reflns_number_total             8152
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo201756z_si_001.cif
_cod_data_source_block           complex3
_cod_database_code               4026788