Atropselective synthesis of N-aryl pyridones via dynamic kinetic resolution enabled by non-covalent interactions
Sweet, Jamie S.; Wang, Ruichen; Manesiotis, Panagiotis; Dingwall, Paul; Knipe, Peter C.; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D2OB00177B

data_7158562
_publ_section_title
;
 Atropselective synthesis of N-aryl pyridones via dynamic kinetic
 resolution enabled by non-covalent interactions
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB00177B
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C31 H22 N2 O2'
_chemical_formula_sum            'C31 H22 N2 O2'
_chemical_formula_weight         454.51
_chemical_name_systematic        (+)-4b
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_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   difmap
_atom_sites_solution_primary     other
_audit_update_record
;
2021-11-24 deposited with the CCDC.	2022-02-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.661(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.3537(3)
_cell_length_b                   12.1471(4)
_cell_length_c                   11.0218(3)
_cell_measurement_reflns_used    3021
_cell_measurement_temperature    299
_cell_measurement_theta_max      71
_cell_measurement_theta_min      4
_cell_volume                     1211.53(7)
_computing_cell_refinement
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_data_reduction
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_pressure         100
_diffrn_ambient_temperature      299
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  'focussing mirrors'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.000
_diffrn_reflns_av_unetI/netI     0.030
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6917
_diffrn_reflns_theta_full        69.278
_diffrn_reflns_theta_max         71.420
_diffrn_reflns_theta_min         4.146
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.620
_exptl_absorpt_correction_T_max  0.93
_exptl_absorpt_correction_T_min  0.76
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_exptl_crystal_colour            clear_pale_yellow
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blocks
_exptl_crystal_F_000             476
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: chloroform/hexane'
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.18
_refine_diff_density_min         -0.27
_refine_ls_abs_structure_details
; 
 Parsons, Flack & Wagner (2013), 
 1957 Friedel Pairs 
;
_refine_ls_abs_structure_Flack   0.02(15)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9451
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         4528
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0370
_refine_ls_shift/su_max          0.0437506
_refine_ls_shift/su_mean         0.0037541
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.05P)^2^ + 0.08P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0943
_refine_ls_wR_factor_gt          0.0886
_refine_ls_wR_factor_ref         0.0943
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              14
_reflns_limit_k_min              -14
_reflns_limit_l_max              13
_reflns_limit_l_min              0
_reflns_number_gt                4016
_reflns_number_total             4528
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   5.01
_oxford_diffrn_Wilson_scale      0.03
_oxford_refine_ls_r_factor_ref   0.0421
_oxford_refine_ls_scale          6.49(12)
_oxford_reflns_number_all        4528
_cod_data_source_file            d2ob00177b2.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_cell_volume        1211.52(6)
_cod_original_sg_symbol_H-M      'P 1 21 1 '
_cod_database_code               7158562
_oxford_refine_reflns_threshold_expression_ref I>-3.0\s(I)
_oxford_hooft_y                  -0.00(14)
_oxford_bijvoet_difference       0.02(15)