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_7134715
_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         'C3 H3 Ga I3 N O2'
_chemical_formula_sum            'C3 H3 Ga I3 N O2'
_chemical_formula_weight         535.48
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-05-01
_audit_creation_method
;
Olex2 1.5
(compiled 2025.04.05 svn.rf049d14d for OlexSys, GUI svn.r7224)
;
_audit_update_record
;
2025-05-01 deposited with the CCDC.	2025-06-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   24.5086(19)
_cell_length_b                   6.6842(5)
_cell_length_c                   6.5526(5)
_cell_measurement_reflns_used    9333
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      68.25
_cell_measurement_theta_min      3.61
_cell_volume                     1073.45(14)
_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      150.00
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.1224
_diffrn_reflns_av_unetI/netI     0.0439
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            32509
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.403
_diffrn_reflns_theta_min         3.607
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    70.927
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.3396
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1576 before and 0.1124 after correction.
The Ratio of minimum to maximum transmission is 0.4509.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    3.313
_exptl_crystal_description       block
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.025
_exptl_crystal_size_mid          0.013
_exptl_crystal_size_min          0.013
_refine_diff_density_max         1.527
_refine_diff_density_min         -1.992
_refine_diff_density_rms         0.334
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.109(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     92
_refine_ls_number_reflns         1951
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0428
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0768P)^2^+2.6258P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1098
_refine_ls_wR_factor_ref         0.1101
_reflns_Friedel_coverage         0.822
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                1922
_reflns_number_total             1951
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc02623g2.cif
_cod_data_source_block           11
_cod_depositor_comments
'Adding full bibliography for 7134715--7134719.cif.'
_cod_database_code               7134715
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.459
_shelx_estimated_absorpt_t_min   0.270
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.891(17)
 0.109(17)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
3.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3)
;
_shelx_res_checksum              45022
_shelx_hkl_checksum              40623
_olex2_submission_special_instructions 'No special instructions were received'