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#$Date: 2025-08-22 00:26:11 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301853 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/04/7100408.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_7100408
loop_
_publ_author_name
'Deevi Basavaiah'
'Jamjanam Srivardhana Rao'
'Anumolu Jaganmohan Rao'
'Raju J. Reddy'
_publ_section_title
;
TiCl4 Catalyzed Tandem Construction of C-C and C-O
Bonds: a Simple and One-Pot Atom-Economical Stereoselective Synthesis of
Spiro-Oxindoles
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/b500224a
_journal_year                    2005
_chemical_formula_moiety         'C20 H18 O4'
_chemical_formula_sum            'C20 H18 O4'
_chemical_formula_weight         322.34
_chemical_melting_point          421.1(10)
_chemical_name_common
;
(1S,5S,7(1')S/1R,5R,7(1')R)-(1-Acetyl-5-methyl-6,8-
dioxabicyclo(3.2.1)octane)-7-spiro-1'-(1',2'-dihydroacenaphthalene-2'-
one)
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_cell_angle_alpha                90.00
_cell_angle_beta                 90.66(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.901(2)
_cell_length_b                   9.0504(13)
_cell_length_c                   14.859(6)
_cell_measurement_temperature    298
_cell_volume                     1600.4(7)
_diffrn_ambient_temperature      298
_exptl_crystal_density_diffrn    1.338
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '147-149 degree centigrade' was
changed to '421.1(10)' - it was converted from degrees Celsius(C) to
Kelvins(K), the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7100408
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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 0.2894(3) 0.3449(3) 0.28374(15) 0.0660(8) Uani 1 1 d . . .
O2 O 0.42632(17) 0.3510(2) 0.11363(15) 0.0446(5) Uani 1 1 d . . .
O3 O 0.38260(16) 0.1412(2) 0.03605(13) 0.0361(5) Uani 1 1 d . . .
O4 O 0.1033(2) 0.1397(3) 0.11124(18) 0.0585(7) Uani 1 1 d . . .
C1 C 0.1836(3) 0.5087(3) 0.1884(2) 0.0444(7) Uani 1 1 d . . .
C2 C 0.1213(4) 0.6012(4) 0.2413(2) 0.0614(10) Uani 1 1 d . . .
H2 H 0.1239 0.5935 0.3037 0.074 Uiso 1 1 calc R . .
C3 C 0.0533(4) 0.7084(5) 0.1987(3) 0.0678(11) Uani 1 1 d . . .
H3 H 0.0107 0.7719 0.2337 0.081 Uiso 1 1 calc R . .
C4 C 0.0486(3) 0.7211(4) 0.1070(3) 0.0548(9) Uani 1 1 d . . .
H4 H 0.0038 0.7943 0.0813 0.066 Uiso 1 1 calc R . .
C5 C 0.1100(3) 0.6261(3) 0.0505(2) 0.0416(7) Uani 1 1 d . . .
C6 C 0.1773(2) 0.5214(3) 0.09452(18) 0.0355(6) Uani 1 1 d . . .
C7 C 0.2442(2) 0.4179(3) 0.04897(18) 0.0331(6) Uani 1 1 d . . .
C8 C 0.2447(3) 0.4196(3) -0.04211(19) 0.0408(7) Uani 1 1 d . . .
H8 H 0.2894 0.3538 -0.0738 0.049 Uiso 1 1 calc R . .
C9 C 0.1761(3) 0.5234(4) -0.0883(2) 0.0476(8) Uani 1 1 d . . .
H9 H 0.1751 0.5228 -0.1509 0.057 Uiso 1 1 calc R . .
C10 C 0.1110(3) 0.6243(3) -0.0443(2) 0.0458(7) Uani 1 1 d . . .
H10 H 0.0677 0.6916 -0.0769 0.055 Uiso 1 1 calc R . .
C11 C 0.2630(3) 0.3875(4) 0.21017(19) 0.0445(7) Uani 1 1 d . . .
C12 C 0.3081(2) 0.3263(3) 0.11895(18) 0.0360(6) Uani 1 1 d . . .
C13 C 0.3003(2) 0.1569(3) 0.10458(18) 0.0364(6) Uani 1 1 d . . .
C14 C 0.3361(3) 0.0619(4) 0.1850(2) 0.0524(8) Uani 1 1 d . . .
H14A H 0.2838 0.0775 0.2337 0.063 Uiso 1 1 calc R . .
H14B H 0.3322 -0.0414 0.1680 0.063 Uiso 1 1 calc R . .
C15 C 0.4548(4) 0.0969(5) 0.2185(3) 0.0675(11) Uani 1 1 d . . .
H15A H 0.4523 0.1816 0.2584 0.081 Uiso 1 1 calc R . .
H15B H 0.4834 0.0135 0.2528 0.081 Uiso 1 1 calc R . .
C16 C 0.5345(3) 0.1298(4) 0.1421(3) 0.0592(9) Uani 1 1 d . . .
H16A H 0.5999 0.1820 0.1653 0.071 Uiso 1 1 calc R . .
H16B H 0.5598 0.0378 0.1156 0.071 Uiso 1 1 calc R . .
C17 C 0.4769(2) 0.2223(3) 0.0712(2) 0.0420(7) Uani 1 1 d . . .
C18 C 0.5490(3) 0.2696(4) -0.0060(3) 0.0581(9) Uani 1 1 d . . .
H18A H 0.5758 0.1839 -0.0371 0.087 Uiso 1 1 calc R . .
H18B H 0.6117 0.3258 0.0165 0.087 Uiso 1 1 calc R . .
H18C H 0.5054 0.3295 -0.0468 0.087 Uiso 1 1 calc R . .
C19 C 0.1863(3) 0.1076(3) 0.0695(2) 0.0416(7) Uani 1 1 d . . .
C20 C 0.1813(3) 0.0161(4) -0.0147(2) 0.0494(8) Uani 1 1 d . . .
H20A H 0.1048 -0.0113 -0.0272 0.074 Uiso 1 1 calc R . .
H20B H 0.2258 -0.0715 -0.0065 0.074 Uiso 1 1 calc R . .
H20C H 0.2100 0.0723 -0.0641 0.074 Uiso 1 1 calc R . .
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 C11 1.198(4) . ?
O2 C12 1.427(3) . ?
O2 C17 1.458(4) . ?
O3 C13 1.428(3) . ?
O3 C17 1.434(4) . ?
O4 C19 1.208(4) . ?
C1 C2 1.372(4) . ?
C1 C6 1.401(4) . ?
C1 C11 1.481(4) . ?
C2 C3 1.409(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.367(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.412(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.398(4) . ?
C5 C10 1.410(4) . ?
C6 C7 1.407(4) . ?
C7 C8 1.354(4) . ?
C7 C12 1.526(4) . ?
C8 C9 1.417(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.368(5) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.565(4) . ?
C12 C13 1.551(4) . ?
C13 C19 1.514(4) . ?
C13 C14 1.529(4) . ?
C14 C15 1.526(6) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.517(6) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.505(5) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.503(5) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C20 1.501(5) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139179447
