Non-hydrogen bond catalyst-mediated diastereoselective conjugate additions of 5H-oxazol-4-ones to o-hydroxyphenyl-substituted p-quinone methides.
Wang, Ziyang; Huang, Anqi; Fang, Fang; Li, Pengfei; Liu, Guokai; Li, Wenjun; Organic & biomolecular chemistry 18 (2020) 6807–6811; doi:10.1039/d0ob01558j

data_7157674
_publ_section_title
;
 Non-hydrogen bond catalyst-mediated diastereoselective conjugate
 additions of 5H-oxazol-4-ones to o-hydroxyphenyl-substituted p-quinone
 methides.
;
_journal_issue                   35
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6807
_journal_page_last               6811
_journal_paper_doi               10.1039/d0ob01558j
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C31 H34 Br N O4'
_chemical_formula_sum            'C31 H34 Br N O4'
_chemical_formula_weight         564.50
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-09-28
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-07-21 deposited with the CCDC.	2020-08-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.138(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.805(2)
_cell_length_b                   28.766(4)
_cell_length_c                   9.1158(16)
_cell_measurement_reflns_used    9826
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.523
_cell_measurement_theta_min      2.368
_cell_volume                     2804.8(8)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker PHOTO 100 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker PHOTO 100 area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0548
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            43790
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.559
_diffrn_reflns_theta_min         2.365
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_exptl_absorpt_coefficient_mu    1.501
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5737
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_description       block
_exptl_crystal_F_000             1176
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.39
_refine_diff_density_max         0.634
_refine_diff_density_min         -0.719
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       0.0042(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         6427
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0333
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0211P)^2^+2.7926P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0734
_refine_ls_wR_factor_ref         0.0758
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5698
_reflns_number_total             6427
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob01558j2.cif
_cod_data_source_block           cxy0498_0m
_cod_depositor_comments          'Adding full bibliography for 7157674.cif.'
_cod_original_cell_volume        2804.7(9)
_cod_database_code               7157674
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.592
_shelx_estimated_absorpt_t_min   0.533
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14), C20(H20), C27(H27),
 C28(H28), C30(H30)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C22(H22A,H22B,
 H22C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C31(H31A,H31B,H31C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2), O3(H3)
;
_olex2_submission_special_instructions 'No special instructions were received'