Unexpected formal [4 + 2]-cycloaddition of chalcone imines and homophthalic anhydrides: preparation of dihydropyridin-2(1<i>H</i>)-ones.
Guranova, Natalia; Golubev, Pavel; Bakulina, Olga; Dar'in, Dmitry; Kantin, Grigory; Krasavin, Mikhail; Organic & biomolecular chemistry 19 (2021) 3829–3833; doi:10.1039/d1ob00534k

data_7158008
_publ_section_title
;
 Unexpected formal [4 + 2]-cycloaddition of chalcone imines and
 homophthalic anhydrides: preparation of dihydropyridin-2(1<i>H</i>)-ones.
;
_journal_issue                   17
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3829
_journal_page_last               3833
_journal_paper_doi               10.1039/d1ob00534k
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C31 H25 N O3'
_chemical_formula_sum            'C31 H25 N O3'
_chemical_formula_weight         459.52
_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   mixed
_audit_creation_date             2021-03-03
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6257)
;
_audit_update_record
;
2021-03-03 deposited with the CCDC.	2021-04-05 downloaded from the CCDC.
;
_cell_angle_alpha                84.510(2)
_cell_angle_beta                 87.428(2)
_cell_angle_gamma                78.784(2)
_cell_formula_units_Z            2
_cell_length_a                   5.71200(10)
_cell_length_b                   10.0398(2)
_cell_length_c                   21.6602(3)
_cell_measurement_reflns_used    6424
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.1060
_cell_measurement_theta_min      2.0490
_cell_volume                     1212.40(4)
_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      293(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_av_unetI/netI     0.0435
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            11518
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.483
_diffrn_reflns_theta_min         2.050
_exptl_absorpt_coefficient_mu    0.641
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_description       prism
_exptl_crystal_F_000             484
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     321
_refine_ls_number_reflns         4515
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0451
_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^)+(0.0750P)^2^+0.1796P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1198
_refine_ls_wR_factor_ref         0.1258
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3839
_reflns_number_total             4515
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob00534k2.cif
_cod_data_source_block           2ver0-8722-14146_zra-521
_cod_depositor_comments
'Adding full bibliography for 7158008--7158009.cif.'
_cod_database_code               7158008
_shelx_shelxl_version_number     2018/3
_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.a Ternary CH refined with riding coordinates:
 C19(H19), C20(H20)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3A), C4(H4), C5(H5), C8(H8), C9(H9), C11(H11), C12(H12), C14(H14),
  C15(H15), C16(H16), C17(H17), C21(H21), C24(H24), C25(H25), C26(H26),
 C27(H27), C28(H28), C30(H30)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_olex2_submission_special_instructions 'No special instructions were received'