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_7134719
_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         'C7 H11 Br3 In N O2'
_chemical_formula_sum            'C7 H11 Br3 In N O2'
_chemical_formula_weight         495.70
_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'
_symmetry_Int_Tables_number      14
_atom_sites_solution_primary     dual
_audit_creation_date             2025-03-14
_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                 100.430(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.0413(4)
_cell_length_b                   20.3742(10)
_cell_length_c                   8.1155(4)
_cell_measurement_reflns_used    9894
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      68.471
_cell_measurement_theta_min      5.955
_cell_volume                     1307.63(11)
_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  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150.0
_diffrn_measured_fraction_theta_full 0.9627
_diffrn_measured_fraction_theta_max 0.9627
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0906
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            40302
_diffrn_reflns_theta_full        66.4792
_diffrn_reflns_theta_max         66.48
_diffrn_reflns_theta_min         5.95
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    25.026
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.4387
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1718 before and 0.1108 after correction.
The Ratio of minimum to maximum transmission is 0.5825.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colorless
_exptl_crystal_colour_primary    colorless
_exptl_crystal_density_diffrn    2.5178
_exptl_crystal_description       block
_exptl_crystal_F_000             914.1210
_exptl_crystal_size_max          0.079
_exptl_crystal_size_mid          0.071
_exptl_crystal_size_min          0.067
_refine_diff_density_max         2.0125
_refine_diff_density_min         -1.0491
_refine_diff_density_rms         0.1948
_refine_ls_d_res_high            0.8407
_refine_ls_d_res_low             7.4315
_refine_ls_goodness_of_fit_ref   1.0169
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    15
_refine_ls_number_parameters     130
_refine_ls_number_reflns         2221
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0169
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0348
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0713P)^2^+1.3624P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0931
_refine_ls_wR_factor_ref         0.0942
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              24
_reflns_limit_k_min              0
_reflns_limit_l_max              9
_reflns_limit_l_min              0
_reflns_number_gt                2084
_reflns_number_total             2221
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d5cc02623g2.cif
_cod_data_source_block           ch1
_cod_depositor_comments
'Adding full bibliography for 7134715--7134719.cif.'
_cod_database_code               7134719
_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.a Secondary CH2 refined with riding coordinates:
 C00B(H00d,H00e)
2.b Idealised Me refined as rotating group:
 C009(H00a,H00b,H00c), C00D(H00f,H00g,H00h), C00E(H00i,H00j,H00k)
;
_olex2_submission_special_instructions 'No special instructions were received'