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_7158009
_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         'C32 H27 N O3'
_chemical_formula_sum            'C32 H27 N O3'
_chemical_formula_weight         473.55
_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   geom
_atom_sites_solution_primary     dual
_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                95.410(2)
_cell_angle_beta                 112.439(2)
_cell_angle_gamma                115.598(3)
_cell_formula_units_Z            2
_cell_length_a                   10.6020(3)
_cell_length_b                   11.2205(3)
_cell_length_c                   13.0016(2)
_cell_measurement_reflns_used    11857
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      76.9960
_cell_measurement_theta_min      3.8630
_cell_volume                     1225.34(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 (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            20378
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.275
_diffrn_reflns_theta_min         3.870
_exptl_absorpt_coefficient_mu    0.650
_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    1.283
_exptl_crystal_description       prism
_exptl_crystal_F_000             500
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         5076
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0414
_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^)+(0.0584P)^2^+0.3683P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1105
_refine_ls_wR_factor_ref         0.1142
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4503
_reflns_number_total             5076
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob00534k2.cif
_cod_data_source_block           1ver0-17269_zra-807(1)
_cod_depositor_comments
;
Adding full bibliography for 7158008--7158009.cif.

2025-03-06
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C21.33 H18 N0.67 O2'
_cod_original_formula_weight         315.70
_cod_original_formula_moiety         '0.67(C32 H27 N O3)'
_cod_original_formula_units_Z            3
_cod_original_cell_volume        1225.33(6)
_cod_database_code               7158009
_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 C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
2.c Aromatic/amide H refined with riding coordinates:
 C32(H32), C30(H30), C26(H26), C28(H28), C9(H9), C24(H24), C31(H31), C22(H22),
 C18(H18), C3(H3), C29(H29), C4(H4), C25(H25), C7(H7), C17(H17), C15(H15),
 C16(H16), C23(H23), C5(H5), C6(H6)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_shelx_res_checksum              28195
_shelx_hkl_checksum              94860
_olex2_submission_special_instructions 'No special instructions were received'