N-heterocyclic carbene-catalyzed amidation of unactivated esters with amino alcohols.
Movassaghi, Mohammad; Schmidt, Michael A.; Organic letters 7 (2005) 2453–2456; doi:10.1021/ol050773y

data_1506584
_publ_section_title
;
 N-heterocyclic carbene-catalyzed amidation of unactivated esters with
 amino alcohols.
;
_journal_issue                   12
_journal_name_full               'Organic letters'
_journal_page_first              2453
_journal_page_last               2456
_journal_paper_doi               10.1021/ol050773y
_journal_volume                  7
_journal_year                    2005
_chemical_formula_sum            'C22 H28 N2 O'
_chemical_formula_weight         336.46
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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                 94.235(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.9026(16)
_cell_length_b                   16.6125(17)
_cell_length_c                   7.8304(8)
_cell_measurement_reflns_used    8703
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      22.5
_cell_measurement_theta_min      2
_cell_volume                     1933.3(3)
_computing_cell_refinement       'SAINT 5 (Bruker-AXS, 2003)'
_computing_data_collection       'SMART 5 (Bruker-AXS, 2003)'
_computing_data_reduction        'SAINT 5 (Bruker-AXS, 2003)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Smart APEX CCD'
_diffrn_measurement_method       'omega and phi 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  0.0501
_diffrn_reflns_av_sigmaI/netI    0.0286
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            25954
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.84
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  0.9944
_exptl_absorpt_correction_T_min  0.8925
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.156
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     234
_refine_ls_number_reflns         3411
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0637
_refine_ls_R_factor_gt           0.0471
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0455P)^2^+0.7451P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1036
_refine_ls_wR_factor_ref         0.1120
_reflns_number_gt                2741
_reflns_number_total             3411
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol050773ysi20050413_041648.cif
_cod_data_source_block           04152final
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1506584