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_7134716
_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         '2(C7 H11 I3 In N O2)'
_chemical_formula_sum            'C14 H22 I6 In2 N2 O4'
_chemical_formula_weight         1273.37
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_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                104.905(2)
_cell_angle_beta                 90.308(2)
_cell_angle_gamma                94.684(2)
_cell_formula_units_Z            2
_cell_length_a                   8.2731(4)
_cell_length_b                   11.0036(6)
_cell_length_c                   17.2172(9)
_cell_measurement_reflns_used    9899
_cell_measurement_temperature    150
_cell_measurement_theta_max      68.21
_cell_measurement_theta_min      2.66
_cell_volume                     1508.99(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    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150.00
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.966
_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  0.0689
_diffrn_reflns_av_unetI/netI     0.0529
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            26168
_diffrn_reflns_point_group_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        66.496
_diffrn_reflns_theta_max         66.496
_diffrn_reflns_theta_min         2.657
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    60.575
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.3106
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1388 before and 0.0755 after correction.
The Ratio of minimum to maximum transmission is 0.4124.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.803
_exptl_crystal_description       block
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.057
_exptl_crystal_size_mid          0.043
_exptl_crystal_size_min          0.038
_refine_diff_density_max         1.889
_refine_diff_density_min         -2.035
_refine_diff_density_rms         0.359
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         5134
_refine_ls_number_restraints     120
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0548
_refine_ls_R_factor_gt           0.0377
_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^)+(0.0565P)^2^+8.2227P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0948
_refine_ls_wR_factor_ref         0.1086
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4434
_reflns_number_total             5134
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc02623g2.cif
_cod_data_source_block           f1
_cod_depositor_comments
'Adding full bibliography for 7134715--7134719.cif.'
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7134716
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.207
_shelx_estimated_absorpt_t_min   0.130
_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
C8 \\sim C00O \\sim C00M \\sim C00L \\sim N00C \\sim C00J: within 2A with sigma
of 0.005 and sigma for terminal atoms of 0.01 within 2A
All non-hydrogen atoms have similar U: within 2A with sigma of 0.01 and sigma
for terminal atoms of 0.02 within 2A
3.a Secondary CH2 refined with riding coordinates:
 C00H(H00A,H00B), C00J(H00L,H00M)
3.b Idealised Me refined as rotating group:
 C00N(H00C,H00D,H00E), C00O(H00N,H00O,H00P), C00P(H00F,H00G,H00H), C00Q(H00I,
 H00J,H00K), C00R(H00Q,H00R,H00S), C8(H8A,H8B,H8C)
;
_olex2_submission_special_instructions 'No special instructions were received'