Copper-catalyzed aerobic hydroxyamination of alkenes of unsaturated keto oximes in EtOH toward cyclic nitrones
Liu, Xiao-Dong; Wang, Qiu-An; Zhu, Yan-Ping; Peng, Zhi-Hong; Li, Jin-Heng; Green Chemistry 24 (2022) 2476–2482; doi:10.1039/D2GC00017B

data_7244381
_publ_section_title
;
 Copper-catalyzed aerobic hydroxyamination of alkenes of unsaturated keto
 oximes in EtOH toward cyclic nitrones
;
_journal_issue                   6
_journal_name_full               'Green Chemistry'
_journal_page_first              2476
_journal_page_last               2482
_journal_paper_doi               10.1039/D2GC00017B
_journal_volume                  24
_journal_year                    2022
_chemical_formula_moiety         C13H17NO2
_chemical_formula_sum            'C13 H17 N O2'
_chemical_formula_weight         219.27
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2021-09-01 deposited with the CCDC.	2022-02-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.1132(13)
_cell_length_b                   5.7769(7)
_cell_length_c                   20.392(3)
_cell_measurement_reflns_used    4006
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.72
_cell_measurement_theta_min      3.67
_cell_volume                     1191.4(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_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           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0203
_diffrn_reflns_av_unetI/netI     0.0172
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            8463
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.495
_diffrn_reflns_theta_min         3.666
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.223
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.150
_exptl_transmission_factor_max   1.0000
_exptl_transmission_factor_min   0.7145
_refine_diff_density_max         0.090
_refine_diff_density_min         -0.104
_refine_diff_density_rms         0.021
_refine_ls_abs_structure_details
; 
 Flack x determined using 893 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   1.1(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         2194
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0321
_refine_ls_R_factor_gt           0.0284
_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^)+(0.0425P)^2^+0.0916P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0738
_refine_ls_wR_factor_ref         0.0772
_reflns_Friedel_coverage         0.928
_reflns_Friedel_fraction_full    0.985
_reflns_Friedel_fraction_max     0.983
_reflns_number_gt                2020
_reflns_number_total             2194
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2gc00017b3.cif
_cod_data_source_block           A
_cod_depositor_comments          'Adding full bibliography for 7244381.cif.'
_cod_original_cell_volume        1191.3(3)
_cod_database_code               7244381
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.982
_shelx_estimated_absorpt_t_max   0.988
_shelx_res_checksum              92258
_shelx_hkl_checksum              45603