Regioselective catalytic asymmetric N-alkylation of isoxazol-5-ones with para-quinone methides.
Qi, Suo-Suo; Jiang, Zhen-Hui; Chu, Ming-Ming; Wang, Yi-Feng; Chen, Xue-Yang; Ju, Wan-Zhen; Xu, Dan-Qian; Organic & biomolecular chemistry 18 (2020) 2398–2404; doi:10.1039/d0ob00393j

data_7157415
_publ_section_title
;
 Regioselective catalytic asymmetric N-alkylation of isoxazol-5-ones with
 para-quinone methides.
;
_journal_issue                   13
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2398
_journal_page_last               2404
_journal_paper_doi               10.1039/d0ob00393j
_journal_volume                  18
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_compound_source        synthesis
_chemical_formula_moiety         chlorophenyl?phenylisoxazol
_chemical_formula_sum            'C31 H34 Cl N O3'
_chemical_formula_weight         504.04
_chemical_melting_point          410
_chemical_name_common            'N-diarylmethane substituted isoxazolinones'
_chemical_name_systematic
(R)-2-((2-chlorophenyl)(3,5-di-tert-butyl-4-hydroxyphenyl)methyl)-4-methyl-3-phenylisoxazol-5(2H)-one
_chemical_properties_physical    stable
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2020-01-14 deposited with the CCDC.	2020-03-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.3478(10)
_cell_length_b                   14.7058(14)
_cell_length_c                   18.6178(17)
_cell_measurement_reflns_used    6763
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      54.719
_cell_measurement_theta_min      4.503
_cell_volume                     2833.1(5)
_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-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_unetI/netI     0.0367
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            14349
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.996
_diffrn_reflns_theta_min         2.590
_exptl_absorpt_coefficient_mu    0.166
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6443
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.182
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1072
_exptl_crystal_preparation       no
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DCM'
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.140
_refine_diff_density_max         0.147
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details
; 
 Flack x determined using 1717 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.06(3)
_refine_ls_extinction_coef       0.038(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     334
_refine_ls_number_reflns         5529
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0407
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0484P)^2^+0.4494P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0955
_refine_ls_wR_factor_ref         0.1045
_reflns_Friedel_coverage         0.774
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                4641
_reflns_number_total             5529
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob00393j2.cif
_cod_data_source_block           mo_dd18232_0m
_cod_depositor_comments          'Adding full bibliography for 7157415.cif.'
_cod_database_code               7157415
_shelx_estimated_absorpt_t_min   0.968
_shelx_estimated_absorpt_t_max   0.977
_shelxl_version_number           2013-4
_shelx_res_checksum              41795