#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/08/7150854.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_7150854
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         'C28 H19 Cl2 N O3'
_chemical_formula_sum            'C28 H19 Cl2 N O3'
_chemical_formula_weight         488.34
_chemical_melting_point          187(2)
_chemical_name_common
;
2,5'-Di((E)-2-chlorobenzylidene)-(1,2,3,4-
tetrahydronaphthalen-1-one) 4-spiro-3'-(piperidine-2',6'-dione)
;
_chemical_name_systematic
;
2,5'-Di[(E)-2-chlorobenzylidene]-[1,2,3,4-tetrahydronaphthalen-1-one]
4-spiro-3'-[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                79.220(1)
_cell_angle_beta                 75.225(1)
_cell_angle_gamma                72.025(1)
_cell_formula_units_Z            2
_cell_length_a                   9.0278(7)
_cell_length_b                   10.5146(9)
_cell_length_c                   13.4184(11)
_cell_measurement_temperature    298
_cell_volume                     1163.34(16)
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0353
_diffrn_reflns_av_sigmaI/netI    0.0364
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11260
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.58
_exptl_absorpt_coefficient_mu    0.311
_exptl_absorpt_correction_T_max  0.9462
_exptl_absorpt_correction_T_min  0.8832
_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    1.394
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         4080
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.997
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0412
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0587P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1006
_refine_ls_wR_factor_ref         0.1064
_reflns_number_gt                3093
_reflns_number_total             4080
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b717843c.txt
_cod_data_source_block           3f
_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_database_code               7150854
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
Cl1 Cl 0.26803(7) 0.48473(6) 0.41912(5) 0.0687(2) Uani 1 1 d . . .
Cl2 Cl 0.59546(9) 0.14210(7) 0.46767(5) 0.0832(2) Uani 1 1 d . . .
O1 O 0.57179(19) -0.20808(14) 0.27794(12) 0.0674(5) Uani 1 1 d . . .
O2 O 0.02771(16) 0.51071(11) 0.12057(10) 0.0469(3) Uani 1 1 d . . .
O3 O 0.22964(17) 0.14028(13) -0.04205(10) 0.0553(4) Uani 1 1 d . . .
N1 N 0.11859(19) 0.31781(15) 0.04740(12) 0.0402(4) Uani 1 1 d . . .
H1N H 0.093(2) 0.3625(17) -0.0045(14) 0.036(5) Uiso 1 1 d . . .
C1 C 0.2560(2) -0.04509(17) 0.14024(13) 0.0357(4) Uani 1 1 d . . .
C2 C 0.1390(2) -0.07946(19) 0.10894(15) 0.0463(5) Uani 1 1 d . . .
H2 H 0.0575 -0.0120 0.0846 0.056 Uiso 1 1 calc R . .
C3 C 0.1427(3) -0.2125(2) 0.11372(16) 0.0565(6) Uani 1 1 d . . .
H3 H 0.0643 -0.2341 0.0921 0.068 Uiso 1 1 calc R . .
C4 C 0.2614(3) -0.3131(2) 0.15019(17) 0.0588(6) Uani 1 1 d . . .
H4 H 0.2655 -0.4028 0.1512 0.071 Uiso 1 1 calc R . .
C5 C 0.3734(3) -0.28134(18) 0.18505(16) 0.0525(5) Uani 1 1 d . . .
H5 H 0.4517 -0.3498 0.2117 0.063 Uiso 1 1 calc R . .
C6 C 0.3720(2) -0.14741(17) 0.18123(14) 0.0385(4) Uani 1 1 d . . .
C7 C 0.4897(2) -0.11841(18) 0.22748(14) 0.0434(5) Uani 1 1 d . . .
C8 C 0.5010(2) 0.02241(17) 0.21088(14) 0.0386(4) Uani 1 1 d . . .
C9 C 0.4187(2) 0.11604(17) 0.13001(14) 0.0377(4) Uani 1 1 d . . .
H9A H 0.4832 0.0977 0.0617 0.045 Uiso 1 1 calc R . .
H9B H 0.4097 0.2081 0.1380 0.045 Uiso 1 1 calc R . .
C10 C 0.2504(2) 0.10169(16) 0.13743(13) 0.0337(4) Uani 1 1 d . . .
C11 C 0.1338(2) 0.15729(16) 0.23507(13) 0.0346(4) Uani 1 1 d . . .
H11A H 0.0337 0.1367 0.2422 0.042 Uiso 1 1 calc R . .
H11B H 0.1771 0.1124 0.2956 0.042 Uiso 1 1 calc R . .
C12 C 0.1026(2) 0.30648(16) 0.23191(13) 0.0329(4) Uani 1 1 d . . .
C13 C 0.0802(2) 0.38809(17) 0.13185(13) 0.0356(4) Uani 1 1 d . . .
C14 C 0.1986(2) 0.18396(17) 0.03995(14) 0.0374(4) Uani 1 1 d . . .
C15 C 0.0904(2) 0.37192(17) 0.31130(13) 0.0381(4) Uani 1 1 d . . .
H15 H 0.0772 0.4643 0.2964 0.046 Uiso 1 1 calc R . .
C16 C 0.0955(2) 0.31478(18) 0.41893(13) 0.0407(5) Uani 1 1 d . . .
C17 C 0.1713(2) 0.3616(2) 0.47700(15) 0.0495(5) Uani 1 1 d . . .
C18 C 0.1737(3) 0.3121(3) 0.57888(19) 0.0724(8) Uani 1 1 d . . .
H18 H 0.2275 0.3437 0.6152 0.087 Uiso 1 1 calc R . .
C19 C 0.0969(4) 0.2165(3) 0.62691(19) 0.0849(9) Uani 1 1 d . . .
H19 H 0.0986 0.1829 0.6960 0.102 Uiso 1 1 calc R . .
C20 C 0.0169(3) 0.1697(2) 0.57310(19) 0.0771(8) Uani 1 1 d . . .
H20 H -0.0371 0.1060 0.6063 0.093 Uiso 1 1 calc R . .
C21 C 0.0171(3) 0.2174(2) 0.46996(15) 0.0545(5) Uani 1 1 d . . .
H21 H -0.0356 0.1843 0.4339 0.065 Uiso 1 1 calc R . .
C22 C 0.5850(2) 0.05347(19) 0.26719(15) 0.0452(5) Uani 1 1 d . . .
H22 H 0.6223 -0.0137 0.3179 0.054 Uiso 1 1 calc R . .
C23 C 0.6257(2) 0.18021(19) 0.25890(16) 0.0474(5) Uani 1 1 d . . .
C24 C 0.6357(2) 0.2296(2) 0.34567(17) 0.0537(5) Uani 1 1 d . . .
C25 C 0.6726(2) 0.3496(2) 0.3383(2) 0.0672(7) Uani 1 1 d . . .
H25 H 0.6755 0.3815 0.3977 0.081 Uiso 1 1 calc R . .
C26 C 0.7050(3) 0.4211(2) 0.2432(2) 0.0715(7) Uani 1 1 d . . .
H26 H 0.7290 0.5023 0.2380 0.086 Uiso 1 1 calc R . .
C27 C 0.7024(3) 0.3739(2) 0.1559(2) 0.0719(7) Uani 1 1 d . . .
H27 H 0.7265 0.4224 0.0913 0.086 Uiso 1 1 calc R . .
C28 C 0.6641(2) 0.2548(2) 0.16264(18) 0.0596(6) Uani 1 1 d . . .
H28 H 0.6639 0.2234 0.1023 0.072 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 0.0033 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'
Cl Cl 0.1484 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 C13 128.45(15) . . ?
C14 N1 H1N 116.8(13) . . ?
C13 N1 H1N 114.8(13) . . ?
C6 C1 C2 118.60(16) . . ?
C6 C1 C10 120.37(15) . . ?
C2 C1 C10 120.88(15) . . ?
C3 C2 C1 120.68(18) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C4 C3 C2 120.35(19) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C5 C4 C3 119.82(19) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 120.89(18) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C5 119.55(17) . . ?
C1 C6 C7 121.88(15) . . ?
C5 C6 C7 118.46(16) . . ?
O1 C7 C8 122.03(17) . . ?
O1 C7 C6 120.17(17) . . ?
C8 C7 C6 117.79(15) . . ?
C22 C8 C7 117.60(16) . . ?
C22 C8 C9 126.16(17) . . ?
C7 C8 C9 116.23(15) . . ?
C8 C9 C10 112.63(14) . . ?
C8 C9 H9A 109.1 . . ?
C10 C9 H9A 109.1 . . ?
C8 C9 H9B 109.1 . . ?
C10 C9 H9B 109.1 . . ?
H9A C9 H9B 107.8 . . ?
C1 C10 C14 110.46(14) . . ?
C1 C10 C11 109.01(14) . . ?
C14 C10 C11 110.41(14) . . ?
C1 C10 C9 110.80(14) . . ?
C14 C10 C9 105.10(14) . . ?
C11 C10 C9 111.04(14) . . ?
C12 C11 C10 112.79(14) . . ?
C12 C11 H11A 109.0 . . ?
C10 C11 H11A 109.0 . . ?
C12 C11 H11B 109.0 . . ?
C10 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
C15 C12 C13 117.41(15) . . ?
C15 C12 C11 126.17(15) . . ?
C13 C12 C11 116.41(14) . . ?
O2 C13 N1 119.39(15) . . ?
O2 C13 C12 124.43(16) . . ?
N1 C13 C12 116.16(15) . . ?
O3 C14 N1 119.70(16) . . ?
O3 C14 C10 123.93(16) . . ?
N1 C14 C10 116.28(15) . . ?
C12 C15 C16 127.40(16) . . ?
C12 C15 H15 116.3 . . ?
C16 C15 H15 116.3 . . ?
C17 C16 C21 117.01(18) . . ?
C17 C16 C15 120.94(18) . . ?
C21 C16 C15 121.94(17) . . ?
C18 C17 C16 121.9(2) . . ?
C18 C17 Cl1 118.59(19) . . ?
C16 C17 Cl1 119.47(15) . . ?
C19 C18 C17 119.9(3) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C19 C20 120.1(2) . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C19 C20 C21 120.0(3) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C20 C21 C16 121.0(2) . . ?
C20 C21 H21 119.5 . . ?
C16 C21 H21 119.5 . . ?
C8 C22 C23 128.05(18) . . ?
C8 C22 H22 116.0 . . ?
C23 C22 H22 116.0 . . ?
C24 C23 C28 116.44(19) . . ?
C24 C23 C22 121.82(19) . . ?
C28 C23 C22 121.67(19) . . ?
C25 C24 C23 122.0(2) . . ?
C25 C24 Cl2 118.14(18) . . ?
C23 C24 Cl2 119.85(16) . . ?
C26 C25 C24 119.6(2) . . ?
C26 C25 H25 120.2 . . ?
C24 C25 H25 120.2 . . ?
C27 C26 C25 120.3(2) . . ?
C27 C26 H26 119.8 . . ?
C25 C26 H26 119.8 . . ?
C26 C27 C28 120.5(3) . . ?
C26 C27 H27 119.8 . . ?
C28 C27 H27 119.8 . . ?
C27 C28 C23 121.1(2) . . ?
C27 C28 H28 119.4 . . ?
C23 C28 H28 119.4 . . ?
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
Cl1 C17 1.738(2) . ?
Cl2 C24 1.731(2) . ?
O1 C7 1.218(2) . ?
O2 C13 1.2232(19) . ?
O3 C14 1.205(2) . ?
N1 C14 1.379(2) . ?
N1 C13 1.380(2) . ?
N1 H1N 0.808(17) . ?
C1 C6 1.390(2) . ?
C1 C2 1.394(2) . ?
C1 C10 1.522(2) . ?
C2 C3 1.378(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.372(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.365(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.396(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.488(2) . ?
C7 C8 1.487(2) . ?
C8 C22 1.338(2) . ?
C8 C9 1.503(2) . ?
C9 C10 1.549(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C14 1.522(2) . ?
C10 C11 1.539(2) . ?
C11 C12 1.500(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C15 1.337(2) . ?
C12 C13 1.477(2) . ?
C15 C16 1.463(2) . ?
C15 H15 0.9300 . ?
C16 C17 1.393(3) . ?
C16 C21 1.398(3) . ?
C17 C18 1.372(3) . ?
C18 C19 1.366(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.379(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.381(3) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 C23 1.466(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.394(3) . ?
C23 C28 1.401(3) . ?
C24 C25 1.382(3) . ?
C25 C26 1.366(3) . ?
C25 H25 0.9300 . ?
C26 C27 1.363(3) . ?
C26 H26 0.9300 . ?
C27 C28 1.381(3) . ?
C27 H27 0.9300 . ?
C28 H28 0.9300 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139190258
