Copper-catalyzed [4 + 2] oxidative annulation of α,β-unsaturated ketoxime acetates with ethyl trifluoropyruvate
Yan, Huan; Xu, Gaochen; Gu, Meng; Zhang, Sai; Wu, Qinghuan; Meng, Jingjing; Zhu, Ning; Fang, Zheng; Duan, Jindian; Guo, Kai; Chemical Communications  (2022) –; doi:10.1039/D2CC01573K

data_7130108
_publ_section_title
;
 Copper-catalyzed [4 + 2] oxidative annulation of \a,\b-unsaturated
 ketoxime acetates with ethyl trifluoropyruvate
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC01573K
_journal_year                    2022
_chemical_formula_moiety         'C16 H14 F3 N O5'
_chemical_formula_sum            'C16 H14 F3 N O5'
_chemical_formula_weight         357.28
_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             2021-05-17
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-01-10 deposited with the CCDC.	2022-05-18 downloaded from the CCDC.
;
_cell_angle_alpha                85.1240(10)
_cell_angle_beta                 79.5830(10)
_cell_angle_gamma                67.9670(10)
_cell_formula_units_Z            6
_cell_length_a                   12.9185(2)
_cell_length_b                   14.1732(2)
_cell_length_c                   14.4149(2)
_cell_measurement_reflns_used    9867
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      54.92
_cell_measurement_theta_min      2.93
_cell_volume                     2405.81(6)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      172.99
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_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  0.0311
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            31488
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.928
_diffrn_reflns_theta_min         2.927
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.740
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.6553
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0903 before and 0.0472 after correction. The Ratio of minimum to maximum transmission is 0.8728. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_description       block
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     682
_refine_ls_number_reflns         9074
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0345
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0442P)^2^+0.7232P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0914
_refine_ls_wR_factor_ref         0.0935
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8437
_reflns_number_total             9074
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc01573k2.cif
_cod_data_source_block           2105130246_0m
_cod_database_code               7130108
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.978
_shelx_estimated_absorpt_t_min   0.964
_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.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C31(H31A,H31B), C47(H47A,H47B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C22(H22), C25(H25),
 C26(H26), C27(H27), C28(H28), C29(H29), C38(H38), C41(H41), C42(H42), C43(H43),
  C44(H44), C45(H45)
2.c Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C16(H16A,H16B,H16C), C21(H21A,H21B,H21C), C32(H32A,H32B,
 H32C), C37(H37A,H37B,H37C), C48(H48A,H48B,H48C)
;
_shelx_res_checksum              78695
_shelx_hkl_checksum              48219
_olex2_submission_special_instructions 'No special instructions were received'