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_7158561
_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_formula_moiety         'C32 H27 N O2'
_chemical_formula_sum            'C32 H27 N O2'
_chemical_formula_weight         457.55
_chemical_melting_point          ?
_chemical_name_systematic        '4j (racemate)'
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-I 2ya'
_symmetry_space_group_name_H-M   'I 1 2/a 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     other
_audit_creation_date             2021-07-15
_audit_creation_method           CRYSTALS_ver_14.61_build_6999
_audit_update_record
;
2021-11-24 deposited with the CCDC.	2022-02-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.3470(18)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   21.811899(14)
_cell_length_b                   9.840500(10)
_cell_length_c                   23.848099(14)
_cell_measurement_reflns_used    27100
_cell_measurement_temperature    293
_cell_measurement_theta_max      71
_cell_measurement_theta_min      5
_cell_volume                     5018.70(3)
_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      293
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.992
_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  0.021
_diffrn_reflns_av_unetI/netI     0.018
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            45155
_diffrn_reflns_theta_full        69.979
_diffrn_reflns_theta_max         71.408
_diffrn_reflns_theta_min         3.781
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.586
_exptl_absorpt_correction_T_max  0.90
_exptl_absorpt_correction_T_min  0.67
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_density_diffrn    1.211
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blocks
_exptl_crystal_F_000             1936
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: chloroform/hexane'
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.13
_refine_diff_density_min         -0.18
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.8816
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         4846
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0410
_refine_ls_shift/su_max          0.0005813
_refine_ls_shift/su_mean         0.0000885
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.06P)^2^ + 2.74P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1100
_refine_ls_wR_factor_gt          0.1058
_refine_ls_wR_factor_ref         0.1100
_reflns_limit_h_max              25
_reflns_limit_h_min              -26
_reflns_limit_k_max              12
_reflns_limit_k_min              0
_reflns_limit_l_max              29
_reflns_limit_l_min              0
_reflns_number_gt                4399
_reflns_number_total             4846
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   4.29
_oxford_diffrn_Wilson_scale      0.19
_oxford_refine_ls_r_factor_ref   0.0441
_oxford_refine_ls_scale          2.47(2)
_oxford_reflns_number_all        4846
_oxford_structure_analysis_title C:\Crystallography\JS-291-1\JS-291-01.cif_od
_cod_data_source_file            d2ob00177b2.cif
_cod_data_source_block           'global_CCDC1'
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value 'not measured' was changed
to '?' -- the value is undefined or not given.

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_sg_symbol_H-M      'I 2/a'
_cod_database_code               7158561
_oxford_refine_reflns_threshold_expression_ref I>-3.0\s(I)