Copper-Catalyzed Diastereoselective O-Transfer Reaction of N-Vinyl-α,β-Unsaturated Nitrones with Ketenes into γ-Lactones through [5+2] Cycloaddition and N-O Bond Cleavage
Liao, Jun-Yi; Wu, Qing-Yan; Lu, Xiuqiang; Zou, Ning; Pan, Cheng-Xue; Liang, Cui; SU, Guifa; Mo, Dong-Liang; Green Chemistry  (2019) –; doi:10.1039/C9GC01811E

data_7234157
_publ_section_title
;
 Copper-Catalyzed Diastereoselective O-Transfer Reaction of
 N-Vinyl-\a,\b-Unsaturated Nitrones with Ketenes into \g-Lactones through
 [5+2] Cycloaddition and N-O Bond Cleavage
;
_journal_name_full               'Green Chemistry'
_journal_paper_doi               10.1039/C9GC01811E
_journal_year                    2019
_chemical_formula_moiety         'C29 H25 N O2'
_chemical_formula_sum            'C29 H25 N O2'
_chemical_formula_weight         419.50
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-10-15
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_audit_update_record
;
2019-05-13 deposited with the CCDC.    2019-09-24 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 109.759(17)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.123(14)
_cell_length_b                   11.404(12)
_cell_length_c                   16.760(18)
_cell_measurement_reflns_used    8491
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.24
_cell_measurement_theta_min      2.20
_cell_volume                     2361(4)
_computing_cell_refinement       'SAINT v8.27A (Bruker, 2012)'
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            25354
_diffrn_reflns_theta_full        25.59
_diffrn_reflns_theta_max         25.59
_diffrn_reflns_theta_min         1.65
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.180
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             888
_refine_diff_density_max         0.528
_refine_diff_density_min         -0.538
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         4388
_refine_ls_number_restraints     684
_refine_ls_restrained_S_all      1.268
_refine_ls_R_factor_all          0.0826
_refine_ls_R_factor_gt           0.0656
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1003P)^2^+1.3480P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1798
_refine_ls_wR_factor_ref         0.1981
_reflns_number_gt                3375
_reflns_number_total             4388
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c9gc01811e2.cif
_cod_data_source_block           aaaa
_cod_original_cell_volume        2360(4)
_cod_database_code               7234157
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
C3 \\sim C5 \\sim C6 \\sim C7 \\sim C8 \\sim C9 \\sim C10 \\sim C11 \\sim C12
\\sim C13 \\sim C14 \\sim C15 \\sim C16 \\sim C17 \\sim C18 \\sim C19 \\sim C20
\\sim C21 \\sim C22 \\sim C23 \\sim C24 \\sim C25 \\sim C27 \\sim C28 \\sim C29
\\sim C30 \\sim C31 \\sim C1AA \\sim C0AA: within 3.8A with sigma of 0.01 and
sigma for terminal atoms of 0.02
3.a Ternary CH refined with riding coordinates:
 C9(H9), C10(H10), C12(H12)
3.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C15(H15), C17(H17), C18(H18), C19(H19), C20(H20), C22(H22), C23(H23),
 C24(H24), C25(H25), C27(H27), C28(H28), C30(H30), C31(H31), C1AA(H1AA),
 C0AA(H0AA)
3.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C29(H29A,H29B,H29C)
;
_olex2_submission_special_instructions 'No special instructions were received'