Group 13 Lewis acid-mediated formation of 5-oxazolone derivatives from <i>tert</i>-butyl isocyanoacetate.
He, Zhou; Ju, Shaoying; Chen, Ting; Zhang, Xinghua; Stephan, Douglas W.; Wu, Yile; Chemical communications (Cambridge, England) 61 (2025) 10582–10585; doi:10.1039/d5cc02623g

data_7134718
_publ_section_title
;
 Group 13 Lewis acid-mediated formation of 5-oxazolone derivatives from
 <i>tert</i>-butyl isocyanoacetate.
;
_journal_issue                   57
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              10582
_journal_page_last               10585
_journal_paper_doi               10.1039/d5cc02623g
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C25 H11 B F15 N O2'
_chemical_formula_sum            'C25 H11 B F15 N O2'
_chemical_formula_weight         653.16
_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             2025-04-02
_audit_creation_method
;
Olex2 1.5
(compiled 2025.03.04 svn.red2d20d0 for OlexSys, GUI svn.r7188)
;
_audit_update_record
;
2025-05-01 deposited with the CCDC.	2025-06-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.532(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.7995(8)
_cell_length_b                   9.9144(5)
_cell_length_c                   19.6671(10)
_cell_measurement_reflns_used    6924
_cell_measurement_temperature    150
_cell_measurement_theta_max      66.33
_cell_measurement_theta_min      4.66
_cell_volume                     2865.7(3)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150.0
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1343
_diffrn_reflns_av_unetI/netI     0.0829
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            61759
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        66.591
_diffrn_reflns_theta_max         66.591
_diffrn_reflns_theta_min         4.663
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.472
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6515
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1199 before and 0.0797 after correction.
The Ratio of minimum to maximum transmission is 0.8651.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.514
_exptl_crystal_description       plate
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.156
_exptl_crystal_size_mid          0.071
_exptl_crystal_size_min          0.013
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       0.0025(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     401
_refine_ls_number_reflns         4934
_refine_ls_number_restraints     30
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.1001
_refine_ls_R_factor_gt           0.0497
_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^)+(0.0712P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1247
_refine_ls_wR_factor_ref         0.1477
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2733
_reflns_number_total             4934
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc02623g2.cif
_cod_data_source_block           777
_cod_depositor_comments
'Adding full bibliography for 7134715--7134719.cif.'
_cod_database_code               7134718
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.981
_shelx_estimated_absorpt_t_min   0.803
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
F00D \\sim C00Y \\sim C011 \\sim F00G \\sim C012 \\sim F00C: within 2A with
sigma of 0.005 and sigma for terminal atoms of 0.01 within 2A
3.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
3.b Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C6(H6A,H6B,H6C), C7(H7A,H7B,H7C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'