#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/08/7150853.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_7150853
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 H21 N O3'
_chemical_formula_sum            'C28 H21 N O3'
_chemical_formula_weight         419.46
_chemical_melting_point          184(2)
_chemical_name_common
;
2,5'-Di((E)-benzylidene)-(1,2,3,4-tetrahydronaphthalen-1-one)
4-spiro-3'-(piperidine-2',6'-dione)
;
_chemical_name_systematic
;
2,5'-Di[(E)-benzylidene]-[1,2,3,4-tetrahydronaphthalen-1-one]
4-spiro-3'-[piperidine-2',6'-dione]
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.108(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.0369(18)
_cell_length_b                   25.751(5)
_cell_length_c                   9.2740(18)
_cell_measurement_temperature    298
_cell_volume                     2145.9(7)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0233
_diffrn_reflns_av_sigmaI/netI    0.0235
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            12584
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.58
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.9817
_exptl_absorpt_correction_T_min  0.9639
_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    1.298
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         3780
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0528
_refine_ls_R_factor_gt           0.0427
_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)+(0.0526P)²+0.3438P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1031
_refine_ls_wR_factor_ref         0.1081
_reflns_number_gt                3097
_reflns_number_total             3780
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b717843c.txt
_cod_data_source_block           3a
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 21/n'
_cod_database_code               7150853
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
O1 O 0.39665(14) 0.24285(5) 0.50025(11) 0.0598(3) Uani 1 1 d . . .
O2 O 0.49069(18) 0.12690(5) -0.27763(12) 0.0782(5) Uani 1 1 d . . .
O3 O 0.30426(14) 0.27618(5) -0.13502(12) 0.0593(3) Uani 1 1 d . . .
N1 N 0.42346(17) 0.20494(5) -0.19979(14) 0.0509(4) Uani 1 1 d . . .
H1N H 0.391(2) 0.2122(7) -0.289(2) 0.063(5) Uiso 1 1 d . . .
C1 C 0.47677(16) 0.27852(6) 0.14098(15) 0.0365(3) Uani 1 1 d . . .
C2 C 0.54705(18) 0.31880(6) 0.07548(17) 0.0476(4) Uani 1 1 d . . .
H2 H 0.5679 0.3153 -0.0201 0.057 Uiso 1 1 calc R . .
C3 C 0.5863(2) 0.36387(7) 0.14994(18) 0.0545(4) Uani 1 1 d . . .
H3 H 0.6336 0.3903 0.1044 0.065 Uiso 1 1 calc R . .
C4 C 0.5558(2) 0.37006(7) 0.29200(19) 0.0549(4) Uani 1 1 d . . .
H4 H 0.5799 0.4009 0.3411 0.066 Uiso 1 1 calc R . .
C5 C 0.48978(19) 0.33039(6) 0.35948(17) 0.0491(4) Uani 1 1 d . . .
H5 H 0.4700 0.3343 0.4553 0.059 Uiso 1 1 calc R . .
C6 C 0.45169(16) 0.28408(6) 0.28601(15) 0.0385(3) Uani 1 1 d . . .
C7 C 0.39629(17) 0.24011(6) 0.36840(15) 0.0412(4) Uani 1 1 d . . .
C8 C 0.34355(16) 0.19314(6) 0.28565(15) 0.0390(4) Uani 1 1 d . . .
C9 C 0.30708(16) 0.20082(6) 0.12478(15) 0.0398(4) Uani 1 1 d . . .
H9A H 0.2178 0.2218 0.1066 0.048 Uiso 1 1 calc R . .
H9B H 0.2881 0.1674 0.0781 0.048 Uiso 1 1 calc R . .
C10 C 0.43802(16) 0.22812(5) 0.06016(14) 0.0355(3) Uani 1 1 d . . .
C11 C 0.57626(16) 0.19305(5) 0.07213(15) 0.0378(3) Uani 1 1 d . . .
H11A H 0.6614 0.2135 0.0507 0.045 Uiso 1 1 calc R . .
H11B H 0.5956 0.1808 0.1713 0.045 Uiso 1 1 calc R . .
C12 C 0.56164(17) 0.14702(6) -0.02759(15) 0.0400(4) Uani 1 1 d . . .
C13 C 0.4915(2) 0.15711(6) -0.17703(16) 0.0505(4) Uani 1 1 d . . .
C14 C 0.38294(18) 0.23969(6) -0.09845(15) 0.0413(4) Uani 1 1 d . . .
C15 C 0.60714(18) 0.09839(6) 0.00085(16) 0.0456(4) Uani 1 1 d . . .
H15 H 0.5895 0.0759 -0.0777 0.055 Uiso 1 1 calc R . .
C16 C 0.67950(17) 0.07368(6) 0.13197(16) 0.0436(4) Uani 1 1 d . . .
C17 C 0.67223(19) 0.01965(6) 0.13899(18) 0.0516(4) Uani 1 1 d . . .
H17 H 0.6271 0.0014 0.0597 0.062 Uiso 1 1 calc R . .
C18 C 0.7300(2) -0.00720(7) 0.2599(2) 0.0605(5) Uani 1 1 d . . .
H18 H 0.7215 -0.0432 0.2628 0.073 Uiso 1 1 calc R . .
C19 C 0.8002(2) 0.01886(8) 0.3763(2) 0.0648(5) Uani 1 1 d . . .
H19 H 0.8396 0.0007 0.4583 0.078 Uiso 1 1 calc R . .
C20 C 0.8120(2) 0.07170(8) 0.3712(2) 0.0658(5) Uani 1 1 d . . .
H20 H 0.8599 0.0893 0.4504 0.079 Uiso 1 1 calc R . .
C21 C 0.75387(19) 0.09951(7) 0.25040(18) 0.0551(5) Uani 1 1 d . . .
H21 H 0.7645 0.1354 0.2483 0.066 Uiso 1 1 calc R . .
C22 C 0.34326(17) 0.14801(6) 0.35716(15) 0.0438(4) Uani 1 1 d . . .
H22 H 0.3798 0.1491 0.4547 0.053 Uiso 1 1 calc R . .
C23 C 0.29286(18) 0.09705(6) 0.30151(16) 0.0447(4) Uani 1 1 d . . .
C24 C 0.1597(2) 0.09059(7) 0.21246(18) 0.0560(4) Uani 1 1 d . . .
H24 H 0.1022 0.1195 0.1837 0.067 Uiso 1 1 calc R . .
C25 C 0.1125(2) 0.04197(8) 0.1667(2) 0.0674(5) Uani 1 1 d . . .
H25 H 0.0231 0.0382 0.1081 0.081 Uiso 1 1 calc R . .
C26 C 0.1968(2) -0.00108(8) 0.2073(2) 0.0695(6) Uani 1 1 d . . .
H26 H 0.1648 -0.0339 0.1756 0.083 Uiso 1 1 calc R . .
C27 C 0.3281(2) 0.00438(8) 0.2947(2) 0.0667(5) Uani 1 1 d . . .
H27 H 0.3857 -0.0247 0.3212 0.080 Uiso 1 1 calc R . .
C28 C 0.3751(2) 0.05295(7) 0.34323(18) 0.0556(4) Uani 1 1 d . . .
H28 H 0.4628 0.0562 0.4047 0.067 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'
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 128.44(13) . . ?
C14 N1 H1N 115.2(12) . . ?
C13 N1 H1N 115.8(12) . . ?
C2 C1 C6 118.28(13) . . ?
C2 C1 C10 120.91(13) . . ?
C6 C1 C10 120.68(13) . . ?
C3 C2 C1 121.00(15) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
C2 C3 C4 120.52(16) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C5 C4 C3 119.36(15) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C6 120.72(15) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C5 120.03(14) . . ?
C1 C6 C7 121.13(13) . . ?
C5 C6 C7 118.65(13) . . ?
O1 C7 C6 120.37(14) . . ?
O1 C7 C8 122.00(14) . . ?
C6 C7 C8 117.62(12) . . ?
C22 C8 C7 117.98(13) . . ?
C22 C8 C9 126.38(14) . . ?
C7 C8 C9 115.45(13) . . ?
C8 C9 C10 110.29(11) . . ?
C8 C9 H9A 109.6 . . ?
C10 C9 H9A 109.6 . . ?
C8 C9 H9B 109.6 . . ?
C10 C9 H9B 109.6 . . ?
H9A C9 H9B 108.1 . . ?
C1 C10 C14 109.97(11) . . ?
C1 C10 C11 108.86(11) . . ?
C14 C10 C11 111.26(12) . . ?
C1 C10 C9 109.97(12) . . ?
C14 C10 C9 106.02(11) . . ?
C11 C10 C9 110.73(12) . . ?
C12 C11 C10 113.72(12) . . ?
C12 C11 H11A 108.8 . . ?
C10 C11 H11A 108.8 . . ?
C12 C11 H11B 108.8 . . ?
C10 C11 H11B 108.8 . . ?
H11A C11 H11B 107.7 . . ?
C15 C12 C13 116.13(13) . . ?
C15 C12 C11 127.87(13) . . ?
C13 C12 C11 115.98(13) . . ?
O2 C13 N1 119.15(14) . . ?
O2 C13 C12 124.93(15) . . ?
N1 C13 C12 115.93(13) . . ?
O3 C14 N1 120.47(13) . . ?
O3 C14 C10 122.95(14) . . ?
N1 C14 C10 116.55(13) . . ?
C12 C15 C16 132.28(14) . . ?
C12 C15 H15 113.9 . . ?
C16 C15 H15 113.9 . . ?
C21 C16 C17 117.41(15) . . ?
C21 C16 C15 125.63(15) . . ?
C17 C16 C15 116.96(14) . . ?
C18 C17 C16 121.67(16) . . ?
C18 C17 H17 119.2 . . ?
C16 C17 H17 119.2 . . ?
C19 C18 C17 120.10(18) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C20 C19 C18 119.53(17) . . ?
C20 C19 H19 120.2 . . ?
C18 C19 H19 120.2 . . ?
C19 C20 C21 121.23(18) . . ?
C19 C20 H20 119.4 . . ?
C21 C20 H20 119.4 . . ?
C20 C21 C16 120.01(17) . . ?
C20 C21 H21 120.0 . . ?
C16 C21 H21 120.0 . . ?
C8 C22 C23 128.34(14) . . ?
C8 C22 H22 115.8 . . ?
C23 C22 H22 115.8 . . ?
C28 C23 C24 117.99(16) . . ?
C28 C23 C22 119.81(15) . . ?
C24 C23 C22 122.12(15) . . ?
C25 C24 C23 120.71(18) . . ?
C25 C24 H24 119.6 . . ?
C23 C24 H24 119.6 . . ?
C26 C25 C24 120.35(18) . . ?
C26 C25 H25 119.8 . . ?
C24 C25 H25 119.8 . . ?
C27 C26 C25 119.91(19) . . ?
C27 C26 H26 120.0 . . ?
C25 C26 H26 120.0 . . ?
C26 C27 C28 120.14(19) . . ?
C26 C27 H27 119.9 . . ?
C28 C27 H27 119.9 . . ?
C27 C28 C23 120.87(17) . . ?
C27 C28 H28 119.6 . . ?
C23 C28 H28 119.6 . . ?
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 C7 1.2245(17) . ?
O2 C13 1.2142(19) . ?
O3 C14 1.2051(18) . ?
N1 C14 1.375(2) . ?
N1 C13 1.383(2) . ?
N1 H1N 0.872(19) . ?
C1 C2 1.389(2) . ?
C1 C6 1.395(2) . ?
C1 C10 1.5210(19) . ?
C2 C3 1.377(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.384(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.368(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.398(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.482(2) . ?
C7 C8 1.484(2) . ?
C8 C22 1.338(2) . ?
C8 C9 1.5063(19) . ?
C9 C10 1.551(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C14 1.5312(18) . ?
C10 C11 1.536(2) . ?
C11 C12 1.5007(19) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C15 1.336(2) . ?
C12 C13 1.484(2) . ?
C15 C16 1.464(2) . ?
C15 H15 0.9300 . ?
C16 C21 1.394(2) . ?
C16 C17 1.395(2) . ?
C17 C18 1.373(2) . ?
C17 H17 0.9300 . ?
C18 C19 1.368(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.366(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.385(2) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 C23 1.465(2) . ?
C22 H22 0.9300 . ?
C23 C28 1.389(2) . ?
C23 C24 1.395(2) . ?
C24 C25 1.375(2) . ?
C24 H24 0.9300 . ?
C25 C26 1.375(3) . ?
C25 H25 0.9300 . ?
C26 C27 1.371(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 ChemSpider 21430352
