Copper-Catalyzed N-O Cleavage of α,β-Unsaturated Ketoxime Acetates toward Structurally Diverse Pyridines.
Zhang, Lei; Duan, Jindian; Xu, Gaochen; Ding, Xiaojuan; Mao, Yiyang; Rong, Binsen; Zhu, Ning; Fang, Zheng; Li, Zhenjiang; Guo, Kai; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.9b03238

data_4037847
_publ_section_title
;
 Copper-Catalyzed N-O Cleavage of \a,\b-Unsaturated Ketoxime Acetates
 toward Structurally Diverse Pyridines.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b03238
_journal_year                    2020
_chemical_formula_moiety         'C22 H16 F3 N O3'
_chemical_formula_sum            'C22 H16 F3 N O3'
_chemical_formula_weight         399.36
_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             2019-03-29
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                102.129(8)
_cell_angle_beta                 99.415(9)
_cell_angle_gamma                118.029(8)
_cell_formula_units_Z            2
_cell_length_a                   9.8831(13)
_cell_length_b                   10.2552(13)
_cell_length_c                   10.8546(13)
_cell_measurement_reflns_used    3794
_cell_measurement_temperature    111(2)
_cell_measurement_theta_max      54.91
_cell_measurement_theta_min      4.462
_cell_volume                     904.5(2)
_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      111.08
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0604
_diffrn_reflns_av_unetI/netI     0.0724
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7942
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         55.323
_diffrn_reflns_theta_min         3.804
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.647
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.4822
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1233 before and 0.0805 after correction. The Ratio of minimum to maximum transmission is 0.6422. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_description       block
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.425
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3404
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.1004
_refine_ls_R_factor_gt           0.0759
_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^)+(0.1186P)^2^+0.8387P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2165
_refine_ls_wR_factor_ref         0.2401
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2441
_reflns_number_total             3404
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b03238_si_002.cif
_cod_data_source_block           1903271269_0m
_cod_database_code               4037847
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.968
_shelx_estimated_absorpt_t_min   0.938
_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:
 C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C18(H18), C19(H19),
 C20(H20), C21(H21), C22(H22)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_shelx_res_checksum              4365
_shelx_hkl_checksum              7669
_olex2_submission_special_instructions 'No special instructions were received'