Enantioselective construction of functionalized oxazoles <i>via</i> anionic stereogenic-at-cobalt(III) complex-catalyzed Ugi-4CR/Wittig reaction sequences.
Wang, Qi-Ming; Peng, Chang-Min; Sun, Yong-En; Yao, Chuan-Zhi; Jiang, Hua-Jie; Yu, Jie; Organic & biomolecular chemistry 23 (2025) 4074–4078; doi:10.1039/d5ob00293a

data_7160483
_publ_section_title
;
 Enantioselective construction of functionalized oxazoles <i>via</i>
 anionic stereogenic-at-cobalt(III) complex-catalyzed Ugi-4CR/Wittig
 reaction sequences.
;
_journal_issue                   17
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4074
_journal_page_last               4078
_journal_paper_doi               10.1039/d5ob00293a
_journal_volume                  23
_journal_year                    2025
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C18 H14 Br Cl N2 O3'
_chemical_formula_sum            'C18 H14 Br Cl N2 O3'
_chemical_formula_weight         421.67
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-10-14
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2025-02-07 deposited with the CCDC.	2025-04-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.368(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.1043(3)
_cell_length_b                   13.4026(4)
_cell_length_c                   12.0631(4)
_cell_measurement_reflns_used    9812
_cell_measurement_temperature    213
_cell_measurement_theta_max      55.010
_cell_measurement_theta_min      2.869
_cell_volume                     1795.27(9)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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      213
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0458
_diffrn_reflns_av_unetI/netI     0.0408
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            24195
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         55.120
_diffrn_reflns_theta_min         3.463
_diffrn_source_current           2.86
_diffrn_source_power             0.1995708
_diffrn_source_voltage           69.78
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.083
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1013 before and 0.0726 after correction.
The Ratio of minimum to maximum transmission is 0.7975.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.560
_exptl_crystal_description       block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
;
 Flack x determined using 2908 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.041(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     453
_refine_ls_number_reflns         6784
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0274
_refine_ls_R_factor_gt           0.0258
_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^)+(0.0254P)^2^+0.2446P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0625
_refine_ls_wR_factor_ref         0.0638
_reflns_Friedel_coverage         0.897
_reflns_Friedel_fraction_full    0.986
_reflns_Friedel_fraction_max     0.977
_reflns_number_gt                6497
_reflns_number_total             6784
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00293a2.cif
_cod_data_source_block           221014wqm
_cod_depositor_comments          'Adding full bibliography for 7160483.cif.'
_cod_database_code               7160483
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.861
_shelx_estimated_absorpt_t_min   0.813
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3), C21(H21)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C5(H5), C6(H6), C8(H8), C9(H9), C11(H11), C15(H15), C16(H16),
 C17(H17), C18(H18), N3(H3A), C23(H23), C24(H24), C26(H26), C27(H27), C29(H29),
 C33(H33), C34(H34), C35(H35), C36(H36)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C32(H32A,H32B,H32C)
;
_shelx_res_checksum              29548
_olex2_submission_special_instructions 'No special instructions were received'