#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/08/7150855.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_7150855
loop_
_publ_author_name
'Basavaiah, Deevi'
'Reddy, Raju Jannapu'
_publ_section_title
;
 Simple and facile synthesis of tetralone-spiro-glutarimides and
 spiro-bisglutarimides from Baylis--Hillman acetates
;
_journal_issue                   6
_journal_name_full               'Organic &  Biomolecular Chemistry'
_journal_page_first              1034
_journal_page_last               1039
_journal_paper_doi               10.1039/b717843c
_journal_volume                  6
_journal_year                    2008
_chemical_formula_moiety         'C27 H26 N2 O4'
_chemical_formula_sum            'C27 H26 N2 O4'
_chemical_formula_weight         442.50
_chemical_melting_point          218(2)
_chemical_name_common
3,3-Spiro-bis((5-(E)-4-ethylbenzylidene)piperidine-2,6-dione)
_chemical_name_systematic
;
3,3-Spiro-bis[{5-(E)-4-ethylbenzylidene}piperidine-2,6-dione]
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                101.142(1)
_cell_angle_beta                 108.914(1)
_cell_angle_gamma                105.628(1)
_cell_formula_units_Z            2
_cell_length_a                   10.0689(7)
_cell_length_b                   10.7855(8)
_cell_length_c                   12.4469(9)
_cell_measurement_temperature    298
_cell_volume                     1171.60(15)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Ortep-3 for Windows/Platon'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_sigmaI/netI    0.0291
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11347
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.82
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.9783
_exptl_absorpt_correction_T_min  0.9669
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-Bruker Nonius area detector scaling and absorption correction - V2.10'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rectangular
_exptl_crystal_F_000             468
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.448
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         4099
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0803
_refine_ls_R_factor_gt           0.0617
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1150P)²+0.1351P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1824
_refine_ls_wR_factor_ref         0.1963
_reflns_number_gt                2930
_reflns_number_total             4099
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b717843c.txt
_cod_data_source_block           4d
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P -1 '
_cod_database_code               7150855
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O3 O 0.40557(18) 0.14994(16) 0.82589(15) 0.0598(5) Uani 1 1 d . . .
O2 O 0.6133(2) 0.15188(18) 1.10355(15) 0.0635(5) Uani 1 1 d . . .
N1 N 0.7251(2) 0.0159(2) 1.0394(2) 0.0556(6) Uani 1 1 d . . .
N2 N 0.5587(2) 0.3534(2) 0.95587(19) 0.0584(6) Uani 1 1 d . . .
O4 O 0.6906(2) 0.55326(19) 1.09904(19) 0.0841(7) Uani 1 1 d . . .
C18 C 0.5307(3) 0.2224(2) 0.8984(2) 0.0489(6) Uani 1 1 d . . .
C12 C 0.6406(3) 0.0632(2) 0.8200(2) 0.0504(6) Uani 1 1 d . . .
H12A H 0.5408 -0.0051 0.7887 0.061 Uiso 1 1 calc R . .
H12B H 0.6496 0.1036 0.7583 0.061 Uiso 1 1 calc R . .
O1 O 0.8314(2) -0.12894(19) 0.98266(18) 0.0805(6) Uani 1 1 d . . .
C11 C 0.7742(3) -0.0462(2) 0.9598(2) 0.0573(6) Uani 1 1 d . . .
C14 C 0.6615(2) 0.1135(2) 1.0316(2) 0.0500(6) Uani 1 1 d . . .
C13 C 0.6615(2) 0.1726(2) 0.92986(19) 0.0452(5) Uani 1 1 d . . .
C16 C 0.8278(3) 0.4108(2) 1.0662(2) 0.0488(6) Uani 1 1 d . . .
C19 C 0.9507(3) 0.4957(2) 1.1612(2) 0.0540(6) Uani 1 1 d . . .
H19 H 0.9329 0.5635 1.2067 0.065 Uiso 1 1 calc R . .
C10 C 0.7559(3) -0.0017(2) 0.8520(2) 0.0530(6) Uani 1 1 d . . .
C15 C 0.8132(3) 0.2901(2) 0.9745(2) 0.0509(6) Uani 1 1 d . . .
H15A H 0.8941 0.2583 1.0082 0.061 Uiso 1 1 calc R . .
H15B H 0.8244 0.3170 0.9069 0.061 Uiso 1 1 calc R . .
C17 C 0.6919(3) 0.4469(2) 1.0453(2) 0.0589(7) Uani 1 1 d . . .
C9 C 0.8488(3) -0.0136(3) 0.7982(2) 0.0629(7) Uani 1 1 d . . .
H9 H 0.9170 -0.0538 0.8297 0.075 Uiso 1 1 calc R . .
C20 C 1.1067(3) 0.5040(2) 1.2082(2) 0.0536(6) Uani 1 1 d . . .
C6 C 0.8551(3) 0.0299(3) 0.6946(2) 0.0598(7) Uani 1 1 d . . .
C5 C 0.9906(3) 0.1108(3) 0.6999(3) 0.0702(8) Uani 1 1 d . . .
H5 H 1.0772 0.1372 0.7689 0.084 Uiso 1 1 calc R . .
C25 C 1.2071(3) 0.6151(3) 1.3055(2) 0.0697(8) Uani 1 1 d . . .
H25 H 1.1715 0.6761 1.3401 0.084 Uiso 1 1 calc R . .
C7 C 0.7298(3) -0.0072(3) 0.5897(2) 0.0724(8) Uani 1 1 d . . .
H7 H 0.6370 -0.0615 0.5838 0.087 Uiso 1 1 calc R . .
C8 C 0.7396(4) 0.0345(3) 0.4940(3) 0.0820(9) Uani 1 1 d . . .
H8 H 0.6534 0.0071 0.4245 0.098 Uiso 1 1 calc R . .
C21 C 1.1683(3) 0.4189(3) 1.1591(3) 0.0848(10) Uani 1 1 d . . .
H21 H 1.1061 0.3456 1.0911 0.102 Uiso 1 1 calc R . .
C3 C 0.8739(4) 0.1159(3) 0.4989(3) 0.0775(8) Uani 1 1 d . . .
C4 C 0.9987(4) 0.1530(3) 0.6034(3) 0.0808(9) Uani 1 1 d . . .
H4 H 1.0910 0.2081 0.6092 0.097 Uiso 1 1 calc R . .
C22 C 1.3192(3) 0.4413(3) 1.2091(3) 0.0969(11) Uani 1 1 d . . .
H22 H 1.3556 0.3799 1.1760 0.116 Uiso 1 1 calc R . .
C24 C 1.3583(3) 0.6371(4) 1.3520(3) 0.0904(10) Uani 1 1 d . . .
H24 H 1.4225 0.7133 1.4169 0.108 Uiso 1 1 calc R . .
C23 C 1.4175(3) 0.5498(4) 1.3055(3) 0.0894(10) Uani 1 1 d . . .
C26 C 1.5830(4) 0.5779(6) 1.3544(5) 0.151(2) Uani 1 1 d . . .
H26A H 1.6244 0.6245 1.3067 0.181 Uiso 1 1 calc R . .
H26B H 1.6265 0.6403 1.4346 0.181 Uiso 1 1 calc R . .
C2 C 0.8827(6) 0.1617(4) 0.3942(3) 0.1143(13) Uani 1 1 d . . .
H2A H 0.9583 0.1355 0.3735 0.137 Uiso 1 1 calc R . .
H2B H 0.7870 0.1126 0.3268 0.137 Uiso 1 1 calc R . .
C1 C 0.9149(12) 0.2942(6) 0.4077(5) 0.281(5) Uani 1 1 d . . .
H1A H 0.8248 0.3146 0.3936 0.422 Uiso 1 1 calc R . .
H1B H 0.9563 0.3175 0.3518 0.422 Uiso 1 1 calc R . .
H1C H 0.9867 0.3455 0.4875 0.422 Uiso 1 1 calc R . .
C27 C 1.6308(7) 0.4726(9) 1.3595(9) 0.278(5) Uani 1 1 d . . .
H27A H 1.6965 0.4872 1.4401 0.416 Uiso 1 1 calc R . .
H27B H 1.6842 0.4652 1.3085 0.416 Uiso 1 1 calc R . .
H27C H 1.5458 0.3905 1.3335 0.416 Uiso 1 1 calc R . .
H1N H 0.720(3) -0.021(3) 1.090(2) 0.055(8) Uiso 1 1 d . . .
H2N H 0.477(3) 0.386(3) 0.943(2) 0.069(7) Uiso 1 1 d . . .
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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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
C14 N1 C11 128.5(2) . . ?
C14 N1 H1N 117.0(18) . . ?
C11 N1 H1N 113.4(18) . . ?
C18 N2 C17 127.8(2) . . ?
C18 N2 H2N 119.3(16) . . ?
C17 N2 H2N 112.4(16) . . ?
O3 C18 N2 120.5(2) . . ?
O3 C18 C13 122.4(2) . . ?
N2 C18 C13 117.1(2) . . ?
C10 C12 C13 110.72(18) . . ?
C10 C12 H12A 109.5 . . ?
C13 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C13 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
O1 C11 N1 119.6(2) . . ?
O1 C11 C10 124.6(2) . . ?
N1 C11 C10 115.8(2) . . ?
O2 C14 N1 121.4(2) . . ?
O2 C14 C13 122.8(2) . . ?
N1 C14 C13 115.7(2) . . ?
C18 C13 C14 107.68(18) . . ?
C18 C13 C12 109.19(18) . . ?
C14 C13 C12 110.19(18) . . ?
C18 C13 C15 111.31(18) . . ?
C14 C13 C15 107.61(18) . . ?
C12 C13 C15 110.80(18) . . ?
C19 C16 C17 115.5(2) . . ?
C19 C16 C15 128.3(2) . . ?
C17 C16 C15 116.1(2) . . ?
C16 C19 C20 133.4(2) . . ?
C16 C19 H19 113.3 . . ?
C20 C19 H19 113.3 . . ?
C9 C10 C11 118.1(2) . . ?
C9 C10 C12 126.1(2) . . ?
C11 C10 C12 115.6(2) . . ?
C16 C15 C13 113.22(18) . . ?
C16 C15 H15A 108.9 . . ?
C13 C15 H15A 108.9 . . ?
C16 C15 H15B 108.9 . . ?
C13 C15 H15B 108.9 . . ?
H15A C15 H15B 107.7 . . ?
O4 C17 N2 118.7(2) . . ?
O4 C17 C16 124.4(2) . . ?
N2 C17 C16 116.9(2) . . ?
C10 C9 C6 127.1(2) . . ?
C10 C9 H9 116.5 . . ?
C6 C9 H9 116.5 . . ?
C25 C20 C21 116.2(2) . . ?
C25 C20 C19 116.7(2) . . ?
C21 C20 C19 126.8(2) . . ?
C5 C6 C7 117.5(3) . . ?
C5 C6 C9 119.7(2) . . ?
C7 C6 C9 122.8(3) . . ?
C6 C5 C4 120.5(3) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C24 C25 C20 121.4(3) . . ?
C24 C25 H25 119.3 . . ?
C20 C25 H25 119.3 . . ?
C8 C7 C6 121.4(3) . . ?
C8 C7 H7 119.3 . . ?
C6 C7 H7 119.3 . . ?
C7 C8 C3 121.4(3) . . ?
C7 C8 H8 119.3 . . ?
C3 C8 H8 119.3 . . ?
C22 C21 C20 121.2(3) . . ?
C22 C21 H21 119.4 . . ?
C20 C21 H21 119.4 . . ?
C8 C3 C4 117.2(3) . . ?
C8 C3 C2 120.9(3) . . ?
C4 C3 C2 121.9(3) . . ?
C3 C4 C5 121.9(3) . . ?
C3 C4 H4 119.0 . . ?
C5 C4 H4 119.0 . . ?
C23 C22 C21 122.4(3) . . ?
C23 C22 H22 118.8 . . ?
C21 C22 H22 118.8 . . ?
C25 C24 C23 122.0(3) . . ?
C25 C24 H24 119.0 . . ?
C23 C24 H24 119.0 . . ?
C22 C23 C24 116.7(3) . . ?
C22 C23 C26 121.9(3) . . ?
C24 C23 C26 121.3(3) . . ?
C27 C26 C23 118.6(5) . . ?
C27 C26 H26A 107.7 . . ?
C23 C26 H26A 107.7 . . ?
C27 C26 H26B 107.7 . . ?
C23 C26 H26B 107.7 . . ?
H26A C26 H26B 107.1 . . ?
C1 C2 C3 117.0(4) . . ?
C1 C2 H2A 108.0 . . ?
C3 C2 H2A 108.0 . . ?
C1 C2 H2B 108.0 . . ?
C3 C2 H2B 108.0 . . ?
H2A C2 H2B 107.3 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
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
O3 C18 1.213(3) . ?
O2 C14 1.206(3) . ?
N1 C14 1.375(3) . ?
N1 C11 1.383(3) . ?
N1 H1N 0.81(2) . ?
N2 C18 1.360(3) . ?
N2 C17 1.387(3) . ?
N2 H2N 0.96(3) . ?
O4 C17 1.217(3) . ?
C18 C13 1.519(3) . ?
C12 C10 1.497(3) . ?
C12 C13 1.537(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
O1 C11 1.216(3) . ?
C11 C10 1.484(3) . ?
C14 C13 1.524(3) . ?
C13 C15 1.543(3) . ?
C16 C19 1.338(3) . ?
C16 C17 1.479(3) . ?
C16 C15 1.495(3) . ?
C19 C20 1.458(3) . ?
C19 H19 0.9300 . ?
C10 C9 1.333(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C9 C6 1.469(4) . ?
C9 H9 0.9300 . ?
C20 C25 1.385(4) . ?
C20 C21 1.391(4) . ?
C6 C5 1.381(4) . ?
C6 C7 1.384(4) . ?
C5 C4 1.382(4) . ?
C5 H5 0.9300 . ?
C25 C24 1.375(4) . ?
C25 H25 0.9300 . ?
C7 C8 1.374(4) . ?
C7 H7 0.9300 . ?
C8 C3 1.375(4) . ?
C8 H8 0.9300 . ?
C21 C22 1.373(4) . ?
C21 H21 0.9300 . ?
C3 C4 1.378(4) . ?
C3 C2 1.500(5) . ?
C4 H4 0.9300 . ?
C22 C23 1.361(4) . ?
C22 H22 0.9300 . ?
C24 C23 1.376(4) . ?
C24 H24 0.9300 . ?
C23 C26 1.496(5) . ?
C26 C27 1.352(8) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C2 C1 1.342(6) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 24813905
