Development of a Chiral DMAP Catalyst for the Dynamic Kinetic Resolution of Azole Hemiaminals.
Kinens, Artis; Sejejs, Marcis; Kamlet, Adam S.; Piotrowski, David W.; Vedejs, Edwin; Suna, Edgars; The Journal of organic chemistry 82 (2017) 869–886; doi:10.1021/acs.joc.6b02955

data_4032311
_publ_section_title
;
 Development of a Chiral DMAP Catalyst for the Dynamic Kinetic Resolution
 of Azole Hemiaminals.
;
_journal_issue                   2
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              869
_journal_page_last               886
_journal_paper_doi               10.1021/acs.joc.6b02955
_journal_volume                  82
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H14 Br N5 O4'
_chemical_formula_sum            'C17 H14 Br N5 O4'
_chemical_formula_weight         432.24
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 107.8219(17)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.5743(5)
_cell_length_b                   7.6627(4)
_cell_length_c                   18.0825(11)
_cell_measurement_reflns_used    3409
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      0.9
_cell_volume                     1790.61(16)
_computing_structure_refinement  'SHELXL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.98
_diffrn_measured_fraction_theta_max 0.98
_diffrn_measurement_device       'Bruker-Nonius KappaCCD'
_diffrn_measurement_method       '\f and \w scan'
_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  0.0127
_diffrn_reflns_av_sigmaI/netI    0.0850
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            7401
_diffrn_reflns_theta_full        28.0
_diffrn_reflns_theta_max         28.0
_diffrn_reflns_theta_min         1.18
_exptl_absorpt_coefficient_mu    2.330
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.603
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.848
_refine_diff_density_min         -0.797
_refine_diff_density_rms         0.075
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.032(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     487
_refine_ls_number_reflns         7394
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.1263
_refine_ls_R_factor_gt           0.0797
_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^)+(0.0408P)^2^+3.9369P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1501
_refine_ls_wR_factor_ref         0.1697
_reflns_d_resolution_high        0.7603
_reflns_number_gt                4973
_reflns_number_total             7394
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo6b02955_si_002.cif
_cod_data_source_block           ms_173
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4032311
_shelx_title                     ' Compound ms_173'
_shelx_refln_list_code           4
_shelx_f_calc_maximum            211.04
_shelx_f_squared_multiplier      1.000