Catalytic asymmetric Michael and Nef-type sequential reaction of nitroolefin with azlactone to construct oxazole-fused succinimide.
Weng, Rui; Zhou, Yuqiao; Zhang, Yaqin; Feng, Xiaoming; Liu, Xiaohua; Chemical communications (Cambridge, England) 60 (2024) 13384–13387; doi:10.1039/d4cc04858j

data_1572878
_publ_section_title
;
 Catalytic asymmetric Michael and Nef-type sequential reaction of
 nitroolefin with azlactone to construct oxazole-fused succinimide.
;
_journal_issue                   91
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              13384
_journal_page_last               13387
_journal_paper_doi               10.1039/d4cc04858j
_journal_volume                  60
_journal_year                    2024
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C24 H18 N2 O3'
_chemical_formula_sum            'C24 H18 N2 O3'
_chemical_formula_weight         382.40
_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   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2019/1
_audit_update_record
;
2024-03-02 deposited with the CCDC.	2024-10-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.6718(3)
_cell_length_b                   9.0165(3)
_cell_length_c                   24.3506(9)
_cell_measurement_reflns_used    9931
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      79.13
_cell_measurement_theta_min      3.63
_cell_volume                     1903.96(12)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT (Sheldrick 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker D8 Venture Photon II'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0587
_diffrn_reflns_av_unetI/netI     0.0541
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            12022
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         79.911
_diffrn_reflns_theta_min         3.630
_exptl_absorpt_coefficient_mu    0.720
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.5866
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Et2O, PE'
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.138
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details
; 
 Flack x determined using 1449 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.05(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         4015
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0568
_refine_ls_R_factor_gt           0.0533
_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^)+(0.0901P)^2^+0.1835P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1358
_refine_ls_wR_factor_ref         0.1429
_reflns_Friedel_coverage         0.714
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.952
_reflns_number_gt                3719
_reflns_number_total             4015
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc04858j2.cif
_cod_data_source_block           xjx033
_cod_depositor_comments          'Adding full bibliography for 1572878.cif.'
_cod_database_code               1572878
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_min   0.715
_shelx_estimated_absorpt_t_max   0.907
_shelx_res_checksum              55699
_shelx_hkl_checksum              3560