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_7134717
_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         '3(C3 H3 Cl3 Ga N O2), 1(C7 H8)'
_chemical_formula_sum            'C16 H17 Cl9 Ga3 N3 O6'
_chemical_formula_weight         875.54
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-03-13
_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                 134.875(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   43.189(4)
_cell_length_b                   6.5024(6)
_cell_length_c                   30.529(3)
_cell_measurement_reflns_used    9933
_cell_measurement_temperature    150
_cell_measurement_theta_max      68.40
_cell_measurement_theta_min      2.89
_cell_volume                     6075.6(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
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.1125
_diffrn_reflns_av_unetI/netI     0.0579
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       50
_diffrn_reflns_limit_h_min       -50
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            40415
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        66.594
_diffrn_reflns_theta_max         66.594
_diffrn_reflns_theta_min         2.888
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    10.734
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5077
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1524 before and 0.0965 after correction.
The Ratio of minimum to maximum transmission is 0.6741.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.914
_exptl_crystal_description       plate
_exptl_crystal_F_000             3424
_exptl_crystal_size_max          0.0432
_exptl_crystal_size_mid          0.0305
_exptl_crystal_size_min          0.026
_refine_diff_density_max         1.102
_refine_diff_density_min         -0.691
_refine_diff_density_rms         0.134
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     448
_refine_ls_number_reflns         5361
_refine_ls_number_restraints     205
_refine_ls_restrained_S_all      1.104
_refine_ls_R_factor_all          0.0686
_refine_ls_R_factor_gt           0.0622
_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^)+(0.0532P)^2^+72.9668P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1624
_refine_ls_wR_factor_ref         0.1661
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4651
_reflns_number_total             5361
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc02623g2.cif
_cod_data_source_block           6666
_cod_depositor_comments
'Adding full bibliography for 7134715--7134719.cif.'
_cod_original_cell_volume        6075.6(12)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7134717
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.768
_shelx_estimated_absorpt_t_min   0.654
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 Ga03-N00T \\sim Ga03-N00U
 with sigma of 0.02
 O00Q-C00U \\sim O00R-C1AA
 with sigma of 0.02
 O00Q-C00V \\sim O00R-C2AA
 with sigma of 0.02
 C00S-N00T \\sim C00T-N00U
 with sigma of 0.02
 C00S-C00V \\sim C00T-C2AA
 with sigma of 0.02
 N00T-C00U \\sim N00U-C1AA
 with sigma of 0.02
 C00V-O00X \\sim C2AA-O00Y
 with sigma of 0.02
 Ga03-C00S \\sim Ga03-C00T
 with sigma of 0.04
 Ga03-C00U \\sim Ga03-C1AA
 with sigma of 0.04
 O00Q-C00S \\sim O00R-C00T
 with sigma of 0.04
 O00Q-N00T \\sim O00R-N00U
 with sigma of 0.04
 O00Q-O00X \\sim O00R-O00Y
 with sigma of 0.04
 C00S-C00U \\sim C00T-C1AA
 with sigma of 0.04
 C00S-O00X \\sim C00T-O00Y
 with sigma of 0.04
 N00T-C00V \\sim N00U-C2AA
 with sigma of 0.04
 C00U-C00V \\sim C1AA-C2AA
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
C013 \\sim C010 \\sim C011 \\sim C00Z \\sim C00W \\sim C012 \\sim C00Y: within
2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
C5 \\sim C0 \\sim C00{ \\sim C4 \\sim C6 \\sim C00X \\sim C0AA: within 2A with
sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
C1AA \\sim N00T \\sim Ga03 \\sim Cl0C \\sim Cl00 \\sim C00S \\sim C00U \\sim
C00V \\sim O00Q \\sim O00X: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02 within 2A
Ga06 \\sim Cl0B \\sim Cl4 \\sim N00U \\sim C00T \\sim C1AA \\sim C2AA \\sim
O00R \\sim O00Y: within 2A with sigma of 0.01 and sigma for terminal atoms of
0.02 within 2A
4. Others
 Sof(C0)=Sof(C00{)=Sof(H00{)=Sof(C6)=Sof(H6)=Sof(C0AA)=Sof(H0AA)=Sof(C00X)=
 Sof(H00X)=Sof(C4)=Sof(H4)=Sof(C5)=Sof(H5A)=Sof(H5B)=Sof(H5C)=1-FVAR(1)
 Sof(C010)=Sof(C011)=Sof(H011)=Sof(C00W)=Sof(H00W)=Sof(C00Y)=Sof(H00Y)=
 Sof(C012)=Sof(H012)=Sof(C00Z)=Sof(H00Z)=Sof(C013)=Sof(H01A)=Sof(H01B)=
 Sof(H01C)=FVAR(1)
 Fixed Sof: Ga03(0.5) Ga06(0.5) Cl00(0.5) Cl4(0.5) O00Q(0.5) C00S(0.5)
 H00C(0.5) H00D(0.5) N00T(0.5) C00U(0.5) H00U(0.5) C00V(0.5) O00X(0.5)
 N00U(0.5) C00T(0.5) H00E(0.5) H00F(0.5) C1AA(0.5) H1AA(0.5) C2AA(0.5)
 O00R(0.5) O00Y(0.5)
5.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C00R(H00A,H00B), C00S(H00C,H00D), C00T(H00E,H00F)
5.b Aromatic/amide H refined with riding coordinates:
 C00N(H00N), C1(H1), C00U(H00U), C011(H011), C00W(H00W), C00Y(H00Y),
 C012(H012), C00Z(H00Z), C00{(H00{), C6(H6), C0AA(H0AA), C00X(H00X), C4(H4),
 C1AA(H1AA)
5.c Fitted hexagon refined as free rotating group:
 C010(C011,C00W,C00Y,C012,C00Z), C0(C00{,C6,C0AA,C00X,C4)
5.d Idealised Me refined as rotating group:
 C013(H01A,H01B,H01C), C5(H5A,H5B,H5C)
;
_olex2_submission_special_instructions 'No special instructions were received'