Catalytic Enantioselective Pyridine N-Oxidation.
Hsieh, Sheng-Ying; Tang, Y. U.; Crotti, Simone; Stone, Elizabeth; Miller, Scott J.; Journal of the American Chemical Society  (2019) –; doi:10.1021/jacs.9b10414

data_4129091
_publ_section_title
;
 Catalytic Enantioselective Pyridine N-Oxidation.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.9b10414
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H17 F3 N4 O2, 0.5(C4 H8 O2)'
_chemical_formula_sum            'C23 H21 F3 N4 O3'
_chemical_formula_weight         458.44
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     SHELXT
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                93.398(4)
_cell_angle_beta                 91.354(4)
_cell_angle_gamma                90.017(4)
_cell_formula_units_Z            2
_cell_length_a                   8.4638(4)
_cell_length_b                   11.0323(5)
_cell_length_c                   11.3821(6)
_cell_measurement_reflns_used    21684
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      66.5720
_cell_measurement_theta_min      3.8330
_cell_volume                     1060.64(9)
_computing_cell_refinement       'CrysAlisPro 1.171.39.16b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.16b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.16b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB-2014/2 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      93(2)
_diffrn_detector_area_resol_mean 22.2
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Rigaku Saturn 944+ CCD'
_diffrn_measurement_method       \w
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            38146
_diffrn_reflns_point_group_measured_fraction_full 0.939
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_theta_full        66.682
_diffrn_reflns_theta_max         66.682
_diffrn_reflns_theta_min         3.892
_diffrn_source                   'microfocus rotating anode'
_exptl_absorpt_coefficient_mu    0.977
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78933
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
CrysAlisPro 1.171.39.16b (Rigaku Oxford Diffraction, 2015) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_description       Plate
_exptl_crystal_F_000             476
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
; 
 Flack x determined using 2874 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.02(6)
_refine_ls_extinction_coef       0.0076(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     630
_refine_ls_number_reflns         7036
_refine_ls_number_restraints     27
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0334
_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^)+(0.0476P)^2^+0.1974P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0815
_refine_ls_wR_factor_ref         0.0834
_reflns_Friedel_coverage         0.904
_reflns_Friedel_fraction_full    0.891
_reflns_Friedel_fraction_max     0.891
_reflns_number_gt                6617
_reflns_number_total             7036
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b10414_si_004.cif
_cod_data_source_block           007b-19095
_cod_database_code               4129091
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.829
_shelx_estimated_absorpt_t_max   0.953
_shelx_res_checksum              67773
_shelx_hkl_checksum              57893