Knoevenagel-IMHDA and -IMSDA sequences for the synthesis of chiral condensed O,N-, S,N- and N-heterocycles
Kajtár, Mihály; Király, Sándor Balázs; Bényei, Attila; Kiss-Szikszai, Attila; Kónya-Ábrahám, Anita; Horváth, Lilla Borbála; Bősze, Szilvia; Kotschy, Andras; Paczal, Attila; Kurtán, Tibor; RSC Advances 15 (2025) 1230–1248; doi:10.1039/D4RA08353A

data_7249785
_publ_section_title
;
 Knoevenagel-IMHDA and -IMSDA sequences for the synthesis of chiral
 condensed O,N-, S,N- and N-heterocycles
;
_journal_issue                   2
_journal_name_full               'RSC Advances'
_journal_page_first              1230
_journal_page_last               1248
_journal_paper_doi               10.1039/D4RA08353A
_journal_volume                  15
_journal_year                    2025
_chemical_formula_moiety         'C20 H23 N O3 '
_chemical_formula_sum            'C20 H23 N O3'
_chemical_formula_weight         325.39
_chemical_name_common            KM321/1
_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     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2024-11-07 deposited with the CCDC.	2024-12-20 downloaded from the CCDC.
;
_cell_angle_alpha                106.479(5)
_cell_angle_beta                 96.585(5)
_cell_angle_gamma                95.737(5)
_cell_formula_units_Z            2
_cell_length_a                   5.8551(7)
_cell_length_b                   10.1414(12)
_cell_length_c                   15.2595(17)
_cell_measurement_reflns_used    4838
_cell_measurement_temperature    295.(2)
_cell_measurement_theta_max      23.2061
_cell_measurement_theta_min      2.8159
_cell_volume                     854.75(17)
_computing_cell_refinement       'APEX3 v2017.3-0 (Bruker AXS)'
_computing_data_collection       'Bruker Instrument Service vV6.2.6'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 1503)'
_computing_publication_material  'WinGX, PublCIF'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      295.(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device       'Bruker D8 Venture'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       '\w and \p scan'
_diffrn_radiation_monochromator  'multilayer mirror INCOATEC'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           ' Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0588
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            21749
_diffrn_reflns_theta_full        25.24
_diffrn_reflns_theta_max         25.46
_diffrn_reflns_theta_min         2.87
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'INCOATEC I\mS 3.0'
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.97
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.325
_exptl_crystal_size_mid          0.087
_exptl_crystal_size_min          0.071
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.258
_refine_ls_extinction_coef       0.057(14)
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3124
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.1160
_refine_ls_R_factor_gt           0.0962
_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^)+(0.1140P)^2^+2.6496P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3058
_refine_ls_wR_factor_ref         0.3195
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2356
_reflns_number_total             3124
_reflns_threshold_expression     'I > 2\s(I)'
_publcif_datablock.id            {dc8e7557-cf64-4d62-bd38-e07b027209ea}
_cod_data_source_file            d4ra08353a2.cif
_cod_data_source_block           6p
_cod_database_code               7249785
_shelx_res_checksum              5728
_shelx_hkl_checksum              83165
_publcif_funding_html
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