Regio- and Enantioselective Synthesis of Azole Hemiaminal Esters by Lewis Base Catalyzed Dynamic Kinetic Resolution.
Piotrowski, David W.; Kamlet, Adam S.; Dechert-Schmitt, Anne-Marie R; Yan, Jiangli; Brandt, Thomas A.; Xiao, Jun; Wei, Liuqing; Barrila, Mark T.; Journal of the American Chemical Society 138 (2016) 4818–4823; doi:10.1021/jacs.6b00207

data_4125018
_publ_section_title
;
 Regio- and Enantioselective Synthesis of Azole Hemiaminal Esters by Lewis
 Base Catalyzed Dynamic Kinetic Resolution.
;
_journal_issue                   14
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              4818
_journal_page_last               4823
_journal_paper_doi               10.1021/jacs.6b00207
_journal_volume                  138
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_sum            'C24 H20 F N5 O4'
_chemical_formula_weight         461.45
_space_group_crystal_system      trigonal
_space_group_IT_number           152
_space_group_name_Hall           'P 31 2"'
_space_group_name_H-M_alt        'P 31 2 1'
_symmetry_space_group_name_Hall  'P 31 2"'
_symmetry_space_group_name_H-M   'P 31 2 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            6
_cell_length_a                   11.73880(10)
_cell_length_b                   11.73880(10)
_cell_length_c                   27.4082(4)
_cell_measurement_reflns_used    9853
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      67.91
_cell_measurement_theta_min      4.35
_cell_volume                     3270.83(6)
_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-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_unetI/netI     0.0133
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            33122
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.718
_diffrn_reflns_theta_min         4.349
_diffrn_source                   'rotating anode'
_exptl_absorpt_coefficient_mu    0.871
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_T_min  0.928
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_description       PRISM
_exptl_crystal_F_000             1440
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.495
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
; 
 Flack x determined using 1623 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.00(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     319
_refine_ls_number_reflns         3989
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0382
_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^)+(0.0461P)^2^+1.4521P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0952
_refine_ls_wR_factor_ref         0.0961
_reflns_Friedel_coverage         0.727
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.984
_reflns_number_gt                3903
_reflns_number_total             3989
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b00207_si_002.cif
_cod_data_source_block           Z694
_cod_depositor_comments
'Adding full bibliography for 4125018--4125020.cif.'
_cod_original_cell_volume        3270.83(7)
_cod_database_code               4125018
_shelx_estimated_absorpt_t_min   0.733
_shelx_estimated_absorpt_t_max   0.918
_shelx_res_checksum              38131
_shelx_hkl_checksum              7043