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_4125020
_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            'C10 H13 I N6 O3'
_chemical_formula_weight         392.16
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.413(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   4.5885(4)
_cell_length_b                   10.0115(9)
_cell_length_c                   16.2053(13)
_cell_measurement_reflns_used    7615
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.13
_cell_measurement_theta_min      2.73
_cell_volume                     744.42(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      293(2)
_diffrn_measured_fraction_theta_full 0.955
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'montel multilayer optics'
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0527
_diffrn_reflns_av_sigmaI/netI    0.0453
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12126
_diffrn_reflns_theta_full        70.22
_diffrn_reflns_theta_max         70.22
_diffrn_reflns_theta_min         5.19
_exptl_absorpt_coefficient_mu    17.076
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_T_min  .504
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_density_diffrn    1.750
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             384
_refine_diff_density_max         0.727
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.080
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.040(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2625
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0511
_refine_ls_R_factor_gt           0.0355
_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^)+(0.0476P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0787
_refine_ls_wR_factor_ref         0.0864
_reflns_number_gt                2123
_reflns_number_total             2625
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja6b00207_si_004.cif
_cod_data_source_block           z343b
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 4125018--4125020.cif.
;
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               4125020