Divergent synthesis of α-functionalized amides through selective N-O/C-C or N-O/C-C/C-N cleavage of aza-cyclobutanone oxime esters.
Liu, Hua-Wei; Wang, Dian-Liang; Jiang, Nan-Quan; Li, Hai-Yan; Cai, Zhong-Jian; Ji, Shun-Jun; Chemical communications (Cambridge, England) 57 (2021) 9618–9621; doi:10.1039/d1cc03348d

data_7128893
_publ_section_title
;
 Divergent synthesis of \a-functionalized amides through selective N-O/C-C
 or N-O/C-C/C-N cleavage of aza-cyclobutanone oxime esters.
;
_journal_issue                   75
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              9618
_journal_page_last               9621
_journal_paper_doi               10.1039/d1cc03348d
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C22 H20 N2 O3'
_chemical_formula_sum            'C22 H20 N2 O3'
_chemical_formula_weight         360.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   mixed
_audit_block_doi                 10.5517/ccdc.csd.cc27xfzl
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-05-11 deposited with the CCDC.	2021-08-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 114.818(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   25.6297(8)
_cell_length_b                   6.39261(18)
_cell_length_c                   12.4690(3)
_cell_measurement_reflns_used    4992
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      77.1110
_cell_measurement_theta_min      3.7890
_cell_volume                     1854.26(10)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      223(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0634
_diffrn_reflns_av_unetI/netI     0.0493
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12743
_diffrn_reflns_point_group_measured_fraction_full 0.954
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         77.285
_diffrn_reflns_theta_min         3.800
_exptl_absorpt_coefficient_mu    0.701
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85997
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details
;
 Flack x determined using 1305 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.894
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3720
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.894
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0559
_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^)+(0.1000P)^2^+1.3788P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1382
_refine_ls_wR_factor_ref         0.1455
_reflns_Friedel_coverage         0.726
_reflns_Friedel_fraction_full    0.898
_reflns_Friedel_fraction_max     0.874
_reflns_number_gt                3422
_reflns_number_total             3720
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc03348d2.cif
_cod_data_source_block           t
_cod_depositor_comments
'Adding full bibliography for 7128893--7128894.cif.'
_cod_original_cell_volume        1854.25(10)
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               7128893
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.767
_shelx_estimated_absorpt_t_max   0.902
_shelx_res_checksum              32582
_shelx_hkl_checksum              52901