#------------------------------------------------------------------------------
#$Date: 2025-03-07 18:30:27 +0200 (Fri, 07 Mar 2025) $
#$Revision: 298328 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/80/7158009.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_7158009
loop_
_publ_author_name
'Guranova, Natalia'
'Golubev, Pavel'
'Bakulina, Olga'
'Dar'in, Dmitry'
'Kantin, Grigory'
'Krasavin, Mikhail'
_publ_section_title
;
 Unexpected formal [4 + 2]-cycloaddition of chalcone imines and
 homophthalic anhydrides: preparation of dihydropyridin-2(1H)-ones.
;
_journal_issue                   17
_journal_name_full               'Organic & 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/[σ²(Fo²)+(0.0584P)²+0.3683P] where P=(Fo²+2Fc²)/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 > 2σ(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
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.50163(11) 0.44490(8) 0.35835(8) 0.0285(2) Uani 1 1 d . . . . .
O3 O 0.44566(12) 0.34264(9) 0.09945(8) 0.0326(2) Uani 1 1 d . . . . .
O2 O 0.59199(12) 0.57495(9) 0.16957(9) 0.0336(2) Uani 1 1 d . . . . .
N1 N 0.69987(12) 0.65851(10) 0.48610(9) 0.0218(2) Uani 1 1 d . . . . .
C21 C 0.48339(14) 0.85343(12) 0.27232(10) 0.0228(2) Uani 1 1 d . . . . .
C8 C 0.75947(14) 0.80445(12) 0.52429(10) 0.0219(2) Uani 1 1 d . . . . .
C27 C 0.88349(14) 0.88342(12) 0.64755(10) 0.0223(2) Uani 1 1 d . . . . .
C12 C 0.55455(14) 0.57032(12) 0.39182(10) 0.0225(2) Uani 1 1 d . . . . .
C1 C 0.80053(15) 0.60161(12) 0.54211(11) 0.0234(2) Uani 1 1 d . . . . .
H1A H 0.740270 0.501320 0.507434 0.028 Uiso 1 1 calc R . . . .
H1B H 0.828936 0.621979 0.624599 0.028 Uiso 1 1 calc R . . . .
C32 C 0.86509(15) 0.83663(12) 0.73998(11) 0.0238(2) Uani 1 1 d . . . . .
H32 H 0.776251 0.752789 0.724240 0.029 Uiso 1 1 calc R . . . .
C11 C 0.45953(14) 0.63692(12) 0.33206(10) 0.0233(2) Uani 1 1 d . . . . .
H11 H 0.418750 0.656537 0.383614 0.028 Uiso 1 1 calc R . . . .
C10 C 0.57048(14) 0.78031(12) 0.32720(10) 0.0224(2) Uani 1 1 d . . . . .
H10 H 0.618379 0.764960 0.279871 0.027 Uiso 1 1 calc R . . . .
C2 C 0.95008(15) 0.65917(12) 0.53021(11) 0.0238(2) Uani 1 1 d . . . . .
C30 C 1.11124(15) 1.04170(13) 0.87935(11) 0.0274(3) Uani 1 1 d . . . . .
H30 H 1.187843 1.093812 0.956507 0.033 Uiso 1 1 calc R . . . .
C26 C 0.42452(16) 0.90847(13) 0.32955(11) 0.0279(3) Uani 1 1 d . . . . .
H26 H 0.436941 0.898733 0.402474 0.034 Uiso 1 1 calc R . . . .
C28 C 1.01632(15) 1.01085(12) 0.67307(11) 0.0248(3) Uani 1 1 d . . . . .
H28 H 1.029701 1.042843 0.612453 0.030 Uiso 1 1 calc R . . . .
C9 C 0.70054(14) 0.86418(12) 0.45060(10) 0.0230(2) Uani 1 1 d . . . . .
H9 H 0.740611 0.959382 0.475990 0.028 Uiso 1 1 calc R . . . .
C24 C 0.32866(16) 0.99343(14) 0.17181(12) 0.0310(3) Uani 1 1 d . . . . .
H24 H 0.277578 1.040158 0.138508 0.037 Uiso 1 1 calc R . . . .
C13 C 0.31499(15) 0.53650(12) 0.21657(11) 0.0252(3) Uani 1 1 d . . . . .
C19 C 0.46670(16) 0.46912(13) 0.13589(11) 0.0278(3) Uani 1 1 d . . . . .
C31 C 0.97944(16) 0.91545(13) 0.85497(11) 0.0260(3) Uani 1 1 d . . . . .
H31 H 0.967664 0.883470 0.916009 0.031 Uiso 1 1 calc R . . . .
C22 C 0.46341(16) 0.86955(13) 0.16352(11) 0.0281(3) Uani 1 1 d . . . . .
H22 H 0.501945 0.833468 0.123627 0.034 Uiso 1 1 calc R . . . .
C14 C 0.31812(16) 0.45979(12) 0.12641(11) 0.0282(3) Uani 1 1 d . . . . .
C18 C 0.16772(16) 0.51420(13) 0.20054(12) 0.0302(3) Uani 1 1 d . . . . .
H18 H 0.162619 0.562803 0.259427 0.036 Uiso 1 1 calc R . . . .
C3 C 0.94774(17) 0.67380(14) 0.42460(12) 0.0297(3) Uani 1 1 d . . . . .
H3 H 0.853874 0.653175 0.360957 0.036 Uiso 1 1 calc R . . . .
C29 C 1.12853(15) 1.09001(13) 0.78851(11) 0.0276(3) Uani 1 1 d . . . . .
H29 H 1.215503 1.175669 0.804923 0.033 Uiso 1 1 calc R . . . .
C4 C 1.08535(18) 0.71917(14) 0.41382(13) 0.0350(3) Uani 1 1 d . . . . .
H4 H 1.083279 0.728921 0.343045 0.042 Uiso 1 1 calc R . . . .
C25 C 0.34739(16) 0.97783(14) 0.28013(12) 0.0315(3) Uani 1 1 d . . . . .
H25 H 0.308430 1.013711 0.319732 0.038 Uiso 1 1 calc R . . . .
C7 C 1.09210(17) 0.69286(15) 0.62457(13) 0.0341(3) Uani 1 1 d . . . . .
H7 H 1.095427 0.685238 0.696054 0.041 Uiso 1 1 calc R . . . .
C17 C 0.02850(17) 0.42135(14) 0.09899(13) 0.0367(3) Uani 1 1 d . . . . .
H17 H -0.068257 0.407203 0.091213 0.044 Uiso 1 1 calc R . . . .
C15 C 0.17755(17) 0.36879(13) 0.02368(12) 0.0343(3) Uani 1 1 d . . . . .
H15 H 0.180940 0.320035 -0.036214 0.041 Uiso 1 1 calc R . . . .
C16 C 0.03386(18) 0.35022(14) 0.00980(13) 0.0385(3) Uani 1 1 d . . . . .
H16 H -0.058676 0.290147 -0.059247 0.046 Uiso 1 1 calc R . . . .
C23 C 0.38635(17) 0.93913(15) 0.11349(12) 0.0328(3) Uani 1 1 d . . . . .
H23 H 0.373692 0.949065 0.040574 0.039 Uiso 1 1 calc R . . . .
C5 C 1.22498(18) 0.74976(14) 0.50795(14) 0.0362(3) Uani 1 1 d . . . . .
H5 H 1.316337 0.778503 0.500062 0.043 Uiso 1 1 calc R . . . .
C20 C 0.5849(2) 0.34295(15) 0.10794(13) 0.0379(3) Uani 1 1 d . . . . .
H20A H 0.614652 0.385749 0.054080 0.057 Uiso 1 1 calc GR . . . .
H20B H 0.563151 0.249034 0.089158 0.057 Uiso 1 1 calc GR . . . .
H20C H 0.670014 0.394260 0.186259 0.057 Uiso 1 1 calc GR . . . .
C6 C 1.22925(18) 0.73777(17) 0.61365(14) 0.0404(3) Uani 1 1 d . . . . .
H6 H 1.323677 0.759693 0.677383 0.049 Uiso 1 1 calc R . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C19 O3 C20 114.82(11) . . ?
C8 N1 C1 120.04(10) . . ?
C12 N1 C8 121.47(10) . . ?
C12 N1 C1 118.29(9) . . ?
C26 C21 C10 121.40(11) . . ?
C26 C21 C22 118.18(11) . . ?
C22 C21 C10 120.41(11) . . ?
N1 C8 C27 117.58(10) . . ?
C9 C8 N1 119.94(11) . . ?
C9 C8 C27 122.46(10) . . ?
C32 C27 C8 121.03(11) . . ?
C28 C27 C8 119.73(11) . . ?
C28 C27 C32 119.12(11) . . ?
O1 C12 N1 122.20(11) . . ?
O1 C12 C11 121.75(11) . . ?
N1 C12 C11 116.03(10) . . ?
N1 C1 C2 113.25(10) . . ?
C31 C32 C27 120.02(11) . . ?
C12 C11 C10 110.53(10) . . ?
C13 C11 C12 111.85(10) . . ?
C13 C11 C10 115.72(10) . . ?
C21 C10 C11 112.86(10) . . ?
C9 C10 C21 112.67(10) . . ?
C9 C10 C11 106.71(9) . . ?
C3 C2 C1 121.28(11) . . ?
C7 C2 C1 119.78(11) . . ?
C7 C2 C3 118.88(12) . . ?
C29 C30 C31 119.90(12) . . ?
C21 C26 C25 121.34(12) . . ?
C29 C28 C27 120.35(11) . . ?
C8 C9 C10 121.25(10) . . ?
C23 C24 C25 119.58(12) . . ?
C14 C13 C11 124.57(12) . . ?
C18 C13 C11 117.78(12) . . ?
C18 C13 C14 117.59(12) . . ?
O3 C19 C14 111.53(11) . . ?
O2 C19 O3 122.41(13) . . ?
O2 C19 C14 126.05(12) . . ?
C32 C31 C30 120.39(11) . . ?
C21 C22 C23 120.79(12) . . ?
C13 C14 C19 122.56(11) . . ?
C15 C14 C13 120.01(13) . . ?
C15 C14 C19 117.42(12) . . ?
C17 C18 C13 121.80(14) . . ?
C4 C3 C2 120.21(13) . . ?
C30 C29 C28 120.19(11) . . ?
C5 C4 C3 120.15(13) . . ?
C24 C25 C26 119.87(12) . . ?
C6 C7 C2 120.85(13) . . ?
C16 C17 C18 119.99(14) . . ?
C16 C15 C14 121.02(14) . . ?
C17 C16 C15 119.54(13) . . ?
C24 C23 C22 120.24(12) . . ?
C6 C5 C4 120.13(13) . . ?
C5 C6 C7 119.76(14) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C12 1.2249(14) . ?
O3 C19 1.3444(15) . ?
O3 C20 1.4363(19) . ?
O2 C19 1.2089(16) . ?
N1 C8 1.4284(15) . ?
N1 C12 1.3667(16) . ?
N1 C1 1.4697(15) . ?
C21 C10 1.5155(16) . ?
C21 C26 1.3877(18) . ?
C21 C22 1.3896(17) . ?
C8 C27 1.4829(16) . ?
C8 C9 1.3354(17) . ?
C27 C32 1.4027(17) . ?
C27 C28 1.3969(17) . ?
C12 C11 1.5295(17) . ?
C1 C2 1.5087(17) . ?
C32 C31 1.3884(17) . ?
C11 C10 1.5546(16) . ?
C11 C13 1.5182(17) . ?
C10 C9 1.5054(16) . ?
C2 C3 1.3903(18) . ?
C2 C7 1.3878(19) . ?
C30 C31 1.3879(18) . ?
C30 C29 1.3865(19) . ?
C26 C25 1.3893(18) . ?
C28 C29 1.3890(18) . ?
C24 C25 1.3843(19) . ?
C24 C23 1.382(2) . ?
C13 C14 1.4072(19) . ?
C13 C18 1.3957(19) . ?
C19 C14 1.488(2) . ?
C22 C23 1.3934(19) . ?
C14 C15 1.3986(18) . ?
C18 C17 1.3898(19) . ?
C3 C4 1.391(2) . ?
C4 C5 1.380(2) . ?
C7 C6 1.388(2) . ?
C17 C16 1.378(2) . ?
C15 C16 1.380(2) . ?
C5 C6 1.379(2) . ?
