#------------------------------------------------------------------------------
#$Date: 2025-01-16 04:24:26 +0200 (Thu, 16 Jan 2025) $
#$Revision: 297348 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/97/7249785.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7249785
loop_
_publ_author_name
'Kajtár, Mihály'
'Király, Sándor Balázs'
'Bényei, Attila'
'Kiss-Szikszai, Attila'
'Kónya-Ábrahám, Anita'
'Horváth, Lilla Borbála'
'Bősze, Szilvia'
'Kotschy, Andras'
'Paczal, Attila'
'Kurtán, Tibor'
_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       'ω and π 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/[σ²(Fo²)+(0.1140P)²+2.6496P] where P=(Fo²+2Fc²)/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 > 2σ(I)'
_publcif_datablock.id            {dc8e7557-cf64-4d62-bd38-e07b027209ea}
_cod_data_source_file            d4ra08353a2.cif
_cod_data_source_block           6p
_cod_database_code               7249785
_publcif_funding_html
;
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.6915(10) 0.4670(6) 0.8928(3) 0.0559(14) Uani d . . . 1 . .
H H1A 0.563835 0.423233 0.914652 0.067000 Uiso calc U . R 1 . .
H H1AB 0.833068 0.471239 0.933956 0.067000 Uiso calc U . R 1 . .
C C2 0.6502(10) 0.6123(6) 0.8941(4) 0.0605(15) Uani d . . . 1 . .
H H2A 0.624849 0.663385 0.955573 0.073000 Uiso calc U . R 1 . .
H H2AB 0.787044 0.659811 0.880147 0.073000 Uiso calc U . R 1 . .
C C4 0.4481(10) 0.5227(5) 0.7332(3) 0.0537(13) Uani d . . . 1 . .
H H4A 0.571566 0.560812 0.706357 0.064000 Uiso calc U . R 1 . .
H H4AB 0.301538 0.520520 0.695656 0.064000 Uiso calc U . R 1 . .
C C5 0.4865(9) 0.2763(5) 0.6384(3) 0.0492(12) Uani d . . . 1 . .
H H5 0.629761 0.302847 0.616326 0.059000 Uiso calc U . R 1 . .
C C4A 0.4824(9) 0.3754(5) 0.7333(3) 0.0468(12) Uani d . . . 1 . .
H H4AA 0.355105 0.338474 0.759889 0.056000 Uiso calc U . R 1 . .
C C6 0.6435(9) 0.1271(5) 0.7172(3) 0.0502(12) Uani d . . . 1 . .
C C7 0.6654(12) -0.0227(6) 0.7063(5) 0.0764(19) Uani d . . . 1 . .
H H7A 0.512115 -0.076794 0.689733 0.092000 Uiso calc U . R 1 . .
H H7AB 0.753847 -0.057053 0.656608 0.092000 Uiso calc U . R 1 . .
C C8 0.7831(13) -0.0408(7) 0.7935(5) 0.083(2) Uani d . . . 1 . .
H H8A 0.820167 -0.134742 0.781799 0.100000 Uiso calc U . R 1 . .
H H8AB 0.679628 -0.025998 0.839653 0.100000 Uiso calc U . R 1 . .
C C9 1.0016(12) 0.0608(7) 0.8291(5) 0.080(2) Uani d . . . 1 . .
H H9A 1.111774 0.037161 0.786169 0.096000 Uiso calc U . R 1 . .
H H9AB 1.069584 0.052268 0.887893 0.096000 Uiso calc U . R 1 . .
C C9B 0.7119(9) 0.3808(5) 0.7950(3) 0.0460(12) Uani d . . . 1 . .
H H9B 0.836277 0.429450 0.773287 0.055000 Uiso calc U . R 1 . .
C C10 0.9635(10) 0.2092(6) 0.8417(4) 0.0572(14) Uani d . . . 1 . .
C C10A 0.7636(8) 0.2345(5) 0.7850(3) 0.0467(12) Uani d . . . 1 . .
C C12 0.2879(10) 0.6957(5) 0.8429(4) 0.0556(13) Uani d . . . 1 . .
C C13 0.2975(13) 0.7901(7) 0.9402(4) 0.0759(19) Uani d . . . 1 . .
H H13A 0.170352 0.843278 0.942487 0.114000 Uiso calc U . R 1 . .
H H13B 0.441432 0.851803 0.958112 0.114000 Uiso calc U . R 1 . .
H H13C 0.286645 0.735093 0.981852 0.114000 Uiso calc U . R 1 . .
C C15 0.2843(9) 0.2685(5) 0.5664(3) 0.0465(12) Uani d . . . 1 . .
C C16 0.0741(9) 0.1863(5) 0.5586(4) 0.0524(13) Uani d . . . 1 . .
H H16 0.054284 0.134058 0.599044 0.063000 Uiso calc U . R 1 . .
C C17 -0.1068(9) 0.1825(6) 0.4897(4) 0.0595(14) Uani d . . . 1 . .
H H17 -0.246957 0.126456 0.483828 0.071000 Uiso calc U . R 1 . .
C C18 -0.0798(10) 0.2606(6) 0.4306(4) 0.0607(15) Uani d . . . 1 . .
H H18 -0.202436 0.259502 0.385814 0.073000 Uiso calc U . R 1 . .
C C19 0.1257(11) 0.3394(6) 0.4378(4) 0.0648(16) Uani d . . . 1 . .
H H19 0.143705 0.392351 0.397672 0.078000 Uiso calc U . R 1 . .
C C20 0.3087(10) 0.3420(6) 0.5037(4) 0.0598(14) Uani d . . . 1 . .
H H20 0.450641 0.394000 0.506130 0.072000 Uiso calc U . R 1 . .
N N3 0.4492(8) 0.6107(4) 0.8270(3) 0.0511(11) Uani d . . . 1 . .
O O6 0.4886(7) 0.1387(4) 0.6477(3) 0.0625(11) Uani d . . . 1 . .
O O11 1.1028(7) 0.3049(5) 0.8942(3) 0.0716(13) Uani d . . . 1 . .
O O14 0.1343(9) 0.6984(5) 0.7830(3) 0.0836(15) Uani d . . . 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C9B . . 110.2(4) ?
C2 C1 H1A . . 109.600000 ?
C9B C1 H1A . . 109.600000 ?
C2 C1 H1AB . . 109.600000 ?
C9B C1 H1AB . . 109.600000 ?
H1A C1 H1AB . . 108.100000 ?
N3 C2 C1 . . 111.6(4) ?
N3 C2 H2A . . 109.300000 ?
C1 C2 H2A . . 109.300000 ?
N3 C2 H2AB . . 109.300000 ?
C1 C2 H2AB . . 109.300000 ?
H2A C2 H2AB . . 108.000000 ?
N3 C4 C4A . . 110.3(4) ?
N3 C4 H4A . . 109.600000 ?
C4A C4 H4A . . 109.600000 ?
N3 C4 H4AB . . 109.600000 ?
C4A C4 H4AB . . 109.600000 ?
H4A C4 H4AB . . 108.100000 ?
O6 C5 C15 . . 107.1(4) ?
O6 C5 C4A . . 107.8(4) ?
C15 C5 C4A . . 115.7(4) ?
O6 C5 H5 . . 108.700000 ?
C15 C5 H5 . . 108.700000 ?
C4A C5 H5 . . 108.700000 ?
C5 C4A C4 . . 114.2(4) ?
C5 C4A C9B . . 108.6(4) ?
C4 C4A C9B . . 109.1(4) ?
C5 C4A H4AA . . 108.300000 ?
C4 C4A H4AA . . 108.300000 ?
C9B C4A H4AA . . 108.300000 ?
C10A C6 O6 . . 124.6(4) ?
C10A C6 C7 . . 124.9(5) ?
O6 C6 C7 . . 110.4(4) ?
C8 C7 C6 . . 111.2(5) ?
C8 C7 H7A . . 109.400000 ?
C6 C7 H7A . . 109.400000 ?
C8 C7 H7AB . . 109.400000 ?
C6 C7 H7AB . . 109.400000 ?
H7A C7 H7AB . . 108.000000 ?
C7 C8 C9 . . 110.0(6) ?
C7 C8 H8A . . 109.700000 ?
C9 C8 H8A . . 109.700000 ?
C7 C8 H8AB . . 109.700000 ?
C9 C8 H8AB . . 109.700000 ?
H8A C8 H8AB . . 108.200000 ?
C8 C9 C10 . . 113.4(5) ?
C8 C9 H9A . . 108.900000 ?
C10 C9 H9A . . 108.900000 ?
C8 C9 H9AB . . 108.900000 ?
C10 C9 H9AB . . 108.900000 ?
H9A C9 H9AB . . 107.700000 ?
C10A C9B C1 . . 115.5(4) ?
C10A C9B C4A . . 109.3(4) ?
C1 C9B C4A . . 107.4(4) ?
C10A C9B H9B . . 108.100000 ?
C1 C9B H9B . . 108.100000 ?
C4A C9B H9B . . 108.100000 ?
O11 C10 C10A . . 121.6(5) ?
O11 C10 C9 . . 120.7(5) ?
C10A C10 C9 . . 117.6(5) ?
C6 C10A C10 . . 118.3(5) ?
C6 C10A C9B . . 120.6(4) ?
C10 C10A C9B . . 120.6(4) ?
O14 C12 N3 . . 122.7(5) ?
O14 C12 C13 . . 119.3(5) ?
N3 C12 C13 . . 118.0(5) ?
C12 C13 H13A . . 109.500000 ?
C12 C13 H13B . . 109.500000 ?
H13A C13 H13B . . 109.500000 ?
C12 C13 H13C . . 109.500000 ?
H13A C13 H13C . . 109.500000 ?
H13B C13 H13C . . 109.500000 ?
C20 C15 C16 . . 118.5(5) ?
C20 C15 C5 . . 119.2(5) ?
C16 C15 C5 . . 122.3(5) ?
C15 C16 C17 . . 119.6(5) ?
C15 C16 H16 . . 120.200000 ?
C17 C16 H16 . . 120.200000 ?
C18 C17 C16 . . 120.5(5) ?
C18 C17 H17 . . 119.800000 ?
C16 C17 H17 . . 119.800000 ?
C19 C18 C17 . . 119.7(5) ?
C19 C18 H18 . . 120.100000 ?
C17 C18 H18 . . 120.100000 ?
C18 C19 C20 . . 120.8(6) ?
C18 C19 H19 . . 119.600000 ?
C20 C19 H19 . . 119.600000 ?
C19 C20 C15 . . 120.9(5) ?
C19 C20 H20 . . 119.600000 ?
C15 C20 H20 . . 119.600000 ?
C12 N3 C4 . . 118.8(4) ?
C12 N3 C2 . . 124.9(4) ?
C4 N3 C2 . . 115.7(4) ?
C6 O6 C5 . . 116.1(4) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.512(7) ?
C1 C9B . 1.525(7) ?
C1 H1A . 0.970000 ?
C1 H1AB . 0.970000 ?
C2 N3 . 1.465(6) ?
C2 H2A . 0.970000 ?
C2 H2AB . 0.970000 ?
C4 N3 . 1.455(6) ?
C4 C4A . 1.528(7) ?
C4 H4A . 0.970000 ?
C4 H4AB . 0.970000 ?
C5 O6 . 1.444(6) ?
C5 C15 . 1.499(7) ?
C5 C4A . 1.515(7) ?
C5 H5 . 0.980000 ?
C4A C9B . 1.537(6) ?
C4A H4AA . 0.980000 ?
C6 C10A . 1.338(7) ?
C6 O6 . 1.354(6) ?
C6 C7 . 1.500(7) ?
C7 C8 . 1.495(9) ?
C7 H7A . 0.970000 ?
C7 H7AB . 0.970000 ?
C8 C9 . 1.501(10) ?
C8 H8A . 0.970000 ?
C8 H8AB . 0.970000 ?
C9 C10 . 1.504(8) ?
C9 H9A . 0.970000 ?
C9 H9AB . 0.970000 ?
C9B C10A . 1.513(7) ?
C9B H9B . 0.980000 ?
C10 O11 . 1.224(7) ?
C10 C10A . 1.462(7) ?
C12 O14 . 1.216(6) ?
C12 N3 . 1.338(7) ?
C12 C13 . 1.513(8) ?
C13 H13A . 0.960000 ?
C13 H13B . 0.960000 ?
C13 H13C . 0.960000 ?
C15 C20 . 1.380(7) ?
C15 C16 . 1.389(7) ?
C16 C17 . 1.393(7) ?
C16 H16 . 0.930000 ?
C17 C18 . 1.371(8) ?
C17 H17 . 0.930000 ?
C18 C19 . 1.351(9) ?
C18 H18 . 0.930000 ?
C19 C20 . 1.376(8) ?
C19 H19 . 0.930000 ?
C20 H20 . 0.930000 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C1 H1AB O11 . 0.97 2.42 3.049(7) 121.8 ?
C2 H2A O11 2_767 0.97 2.56 3.221(6) 125.6 ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C9B C1 C2 N3 . . . . 54.3(7) ?
O6 C5 C4A C4 . . . . -172.5(4) ?
C15 C5 C4A C4 . . . . -52.7(6) ?
O6 C5 C4A C9B . . . . 65.6(5) ?
C15 C5 C4A C9B . . . . -174.6(4) ?
N3 C4 C4A C5 . . . . -179.3(4) ?
N3 C4 C4A C9B . . . . -57.7(6) ?
C10A C6 C7 C8 . . . . 16.7(9) ?
O6 C6 C7 C8 . . . . -164.7(6) ?
C6 C7 C8 C9 . . . . -49.2(8) ?
C7 C8 C9 C10 . . . . 54.5(9) ?
C2 C1 C9B C10A . . . . 177.5(5) ?
C2 C1 C9B C4A . . . . -60.2(6) ?
C5 C4A C9B C10A . . . . -47.2(5) ?
C4 C4A C9B C10A . . . . -172.1(4) ?
C5 C4A C9B C1 . . . . -173.2(4) ?
C4 C4A C9B C1 . . . . 61.8(5) ?
C8 C9 C10 O11 . . . . 158.0(6) ?
C8 C9 C10 C10A . . . . -25.8(9) ?
O6 C6 C10A C10 . . . . -165.2(5) ?
C7 C6 C10A C10 . . . . 13.2(9) ?
O6 C6 C10A C9B . . . . 7.5(8) ?
C7 C6 C10A C9B . . . . -174.0(6) ?
O11 C10 C10A C6 . . . . 167.8(6) ?
C9 C10 C10A C6 . . . . -8.3(8) ?
O11 C10 C10A C9B . . . . -4.9(8) ?
C9 C10 C10A C9B . . . . 178.9(5) ?
C1 C9B C10A C6 . . . . 133.4(5) ?
C4A C9B C10A C6 . . . . 12.2(7) ?
C1 C9B C10A C10 . . . . -54.0(7) ?
C4A C9B C10A C10 . . . . -175.3(5) ?
O6 C5 C15 C20 . . . . -140.3(5) ?
C4A C5 C15 C20 . . . . 99.4(6) ?
O6 C5 C15 C16 . . . . 37.7(6) ?
C4A C5 C15 C16 . . . . -82.6(6) ?
C20 C15 C16 C17 . . . . -1.4(8) ?
C5 C15 C16 C17 . . . . -179.5(5) ?
C15 C16 C17 C18 . . . . -0.9(8) ?
C16 C17 C18 C19 . . . . 1.6(9) ?
C17 C18 C19 C20 . . . . 0.0(9) ?
C18 C19 C20 C15 . . . . -2.4(9) ?
C16 C15 C20 C19 . . . . 3.1(8) ?
C5 C15 C20 C19 . . . . -178.8(5) ?
O14 C12 N3 C4 . . . . 3.2(8) ?
C13 C12 N3 C4 . . . . -177.8(5) ?
O14 C12 N3 C2 . . . . 173.9(6) ?
C13 C12 N3 C2 . . . . -7.1(8) ?
C4A C4 N3 C12 . . . . -135.4(5) ?
C4A C4 N3 C2 . . . . 53.0(6) ?
C1 C2 N3 C12 . . . . 137.6(6) ?
C1 C2 N3 C4 . . . . -51.4(7) ?
C10A C6 O6 C5 . . . . 11.3(8) ?
C7 C6 O6 C5 . . . . -167.3(5) ?
C15 C5 O6 C6 . . . . -172.8(4) ?
C4A C5 O6 C6 . . . . -47.7(6) ?
loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max
loop_
_publcif_info_exptl_table_header_item
?
