Highly regioselective synthesis of lactams <i>via</i> cascade reaction of α,β-unsaturated ketones, ketoamides, and DBU as a catalyst.
Qin, Xin; Zhang, Jinhai; Wang, Zhan-Yong; Song, Yimei; Yang, Yixiao; Zhang, Wenhai; Liu, Hongxin; RSC advances 13 (2023) 4782–4786; doi:10.1039/d2ra07117g

data_7246395
_publ_section_title
;
 Highly regioselective synthesis of lactams <i>via</i> cascade reaction of
 &#x3b1;,&#x3b2;-unsaturated ketones, ketoamides, and DBU as a catalyst.
;
_journal_issue                   7
_journal_name_full               'RSC advances'
_journal_page_first              4782
_journal_page_last               4786
_journal_paper_doi               10.1039/d2ra07117g
_journal_volume                  13
_journal_year                    2023
_chemical_formula_moiety         'C19 H17 N O3'
_chemical_formula_sum            'C19 H17 N O3'
_chemical_formula_weight         307.33
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-01-11
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-02-19 deposited with the CCDC.	2022-12-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.529(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.4676(17)
_cell_length_b                   22.034(5)
_cell_length_c                   10.852(3)
_cell_measurement_reflns_used    2514
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      26.08
_cell_measurement_theta_min      2.651
_cell_volume                     1520.4(7)
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_unetI/netI     0.0449
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9956
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.365
_diffrn_reflns_theta_min         1.848
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            white
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_description       needle
_exptl_crystal_F_000             648
_refine_diff_density_max         0.511
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3777
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0962
_refine_ls_R_factor_gt           0.0584
_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^)+(0.1193P)^2^+0.4061P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1686
_refine_ls_wR_factor_ref         0.2135
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2493
_reflns_number_total             3777
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ra07117g2.cif
_cod_data_source_block           mo_20220110d_0m
_cod_original_cell_volume        1520.5(7)
_cod_database_code               7246395
_shelx_shelxl_version_number     2018/3
_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 O(H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3), C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C15(H15), C16(H16), C17(H17),
 C18(H18), C19(H19)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_res_checksum              23698
_olex2_submission_special_instructions 'No special instructions were received'