#------------------------------------------------------------------------------
#$Date: 2025-08-19 22:06:29 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301812 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/08/4020812.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_4020812
loop_
_publ_author_name
'Daniele Casarini'
'Stefano Grilli'
'Lodovico Lunazzi'
'Andrea Mazzanti'
_publ_section_title
;
 Conformational Studies by Dynamic NMR. 97.
 Structure, Conformation, Stereodynamics and Enantioseparation
 of Aryl Substituted Norbornanes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              345
_journal_page_last               351
_journal_paper_doi               10.1021/jo035411n
_journal_volume                  69
_journal_year                    2004
_chemical_formula_sum            'C27 H28 O2'
_chemical_formula_weight         384.49
_chemical_melting_point          162
_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                 102.3720(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.8067(8)
_cell_length_b                   7.4743(5)
_cell_length_c                   22.3194(14)
_cell_measurement_temperature    293(2)
_cell_volume                     2086.8(2)
_diffrn_ambient_temperature      293(2)
_exptl_crystal_density_diffrn    1.224
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4020812
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 -0.15763(8) 0.40183(16) 0.02423(6) 0.0678(3) Uani 1 1 d . . .
O2 O 0.52754(9) 0.27201(17) 0.03778(6) 0.0682(3) Uani 1 1 d . . .
C1 C 0.23568(10) 0.01875(17) 0.23181(6) 0.0420(3) Uani 1 1 d . . .
C2 C 0.33121(12) -0.11205(19) 0.24217(7) 0.0542(4) Uani 1 1 d . . .
H2A H 0.3965 -0.0501 0.2393 0.065 Uiso 1 1 calc R . .
H2B H 0.3410 -0.1683 0.2822 0.065 Uiso 1 1 calc R . .
C3 C 0.30148(13) -0.25230(19) 0.19062(8) 0.0583(4) Uani 1 1 d . . .
H3A H 0.3536 -0.2544 0.1649 0.070 Uiso 1 1 calc R . .
H3B H 0.2961 -0.3709 0.2073 0.070 Uiso 1 1 calc R . .
C4 C 0.19282(11) -0.18694(17) 0.15486(7) 0.0473(3) Uani 1 1 d . . .
H4 H 0.1724 -0.2344 0.1130 0.057 Uiso 1 1 calc R . .
C5 C 0.11203(13) -0.22607(19) 0.19471(7) 0.0543(4) Uani 1 1 d . . .
H5A H 0.1207 -0.3466 0.2112 0.065 Uiso 1 1 calc R . .
H5B H 0.0393 -0.2113 0.1716 0.065 Uiso 1 1 calc R . .
C6 C 0.13954(13) -0.08623(19) 0.24597(7) 0.0532(4) Uani 1 1 d . . .
H6A H 0.1588 -0.1437 0.2858 0.064 Uiso 1 1 calc R . .
H6B H 0.0794 -0.0071 0.2456 0.064 Uiso 1 1 calc R . .
C7 C 0.20505(9) 0.02154(16) 0.15820(6) 0.0377(3) Uani 1 1 d . . .
C8 C 0.10334(9) 0.12210(17) 0.12776(5) 0.0375(3) Uani 1 1 d . . .
C9 C 0.02099(10) 0.04037(19) 0.08589(6) 0.0457(3) Uani 1 1 d . . .
H9 H 0.0241 -0.0823 0.0796 0.055 Uiso 1 1 calc R . .
C10 C -0.06516(11) 0.1354(2) 0.05344(7) 0.0517(3) Uani 1 1 d . . .
H10 H -0.1193 0.0756 0.0264 0.062 Uiso 1 1 calc R . .
C11 C -0.07209(10) 0.3175(2) 0.06052(6) 0.0474(3) Uani 1 1 d . . .
C12 C 0.00817(11) 0.4028(2) 0.10195(7) 0.0556(4) Uani 1 1 d . . .
H12 H 0.0046 0.5255 0.1081 0.067 Uiso 1 1 calc R . .
C13 C 0.09380(11) 0.30538(19) 0.13419(7) 0.0506(3) Uani 1 1 d . . .
H13 H 0.1474 0.3656 0.1614 0.061 Uiso 1 1 calc R . .
C14 C 0.29369(9) 0.09045(17) 0.12797(6) 0.0395(3) Uani 1 1 d . . .
C15 C 0.35114(11) 0.24416(18) 0.14743(7) 0.0486(3) Uani 1 1 d . . .
H15 H 0.3371 0.3055 0.1811 0.058 Uiso 1 1 calc R . .
C16 C 0.42902(11) 0.3103(2) 0.11860(7) 0.0520(3) Uani 1 1 d . . .
H16 H 0.4667 0.4134 0.1332 0.062 Uiso 1 1 calc R . .
C17 C 0.44994(11) 0.2221(2) 0.06827(7) 0.0490(3) Uani 1 1 d . . .
C18 C 0.39156(11) 0.0718(2) 0.04647(6) 0.0527(4) Uani 1 1 d . . .
H18 H 0.4038 0.0139 0.0117 0.063 Uiso 1 1 calc R . .
C19 C 0.31507(10) 0.0071(2) 0.07596(6) 0.0465(3) Uani 1 1 d . . .
H19 H 0.2767 -0.0948 0.0608 0.056 Uiso 1 1 calc R . .
C20 C 0.25694(11) 0.18719(18) 0.27107(6) 0.0443(3) Uani 1 1 d . . .
C21 C 0.17402(14) 0.2910(2) 0.28315(8) 0.0587(4) Uani 1 1 d . . .
H21 H 0.1042 0.2628 0.2639 0.070 Uiso 1 1 calc R . .
C22 C 0.19201(18) 0.4351(2) 0.32299(8) 0.0726(5) Uani 1 1 d . . .
H22 H 0.1347 0.5022 0.3302 0.087 Uiso 1 1 calc R . .
C23 C 0.2949(2) 0.4791(3) 0.35198(8) 0.0835(6) Uani 1 1 d . . .
H23 H 0.3076 0.5742 0.3795 0.100 Uiso 1 1 calc R . .
C24 C 0.37792(19) 0.3814(3) 0.33985(10) 0.0938(8) Uani 1 1 d . . .
H24 H 0.4477 0.4120 0.3585 0.113 Uiso 1 1 calc R . .
C25 C 0.35968(14) 0.2381(2) 0.30031(9) 0.0706(5) Uani 1 1 d . . .
H25 H 0.4177 0.1735 0.2929 0.085 Uiso 1 1 calc R . .
C26 C -0.16078(14) 0.5920(3) 0.02611(10) 0.0805(6) Uani 1 1 d . . .
H26A H -0.2242 0.6340 -0.0014 0.121 Uiso 1 1 calc R . .
H26B H -0.0990 0.6399 0.0139 0.121 Uiso 1 1 calc R . .
H26C H -0.1613 0.6305 0.0671 0.121 Uiso 1 1 calc R . .
C27 C 0.59370(15) 0.4191(3) 0.06109(10) 0.0808(6) Uani 1 1 d . . .
H27A H 0.6443 0.4396 0.0357 0.121 Uiso 1 1 calc R . .
H27B H 0.6313 0.3933 0.1022 0.121 Uiso 1 1 calc R . .
H27C H 0.5504 0.5239 0.0611 0.121 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 1.3687(16) . ?
O1 C26 1.423(2) . ?
O2 C17 1.3709(17) . ?
O2 C27 1.417(2) . ?
C1 C20 1.5247(18) . ?
C1 C2 1.5442(19) . ?
C1 C6 1.5486(19) . ?
C1 C7 1.6055(17) . ?
C2 C3 1.543(2) . ?
C3 C4 1.528(2) . ?
C4 C5 1.530(2) . ?
C4 C7 1.5663(17) . ?
C5 C6 1.534(2) . ?
C7 C14 1.5289(18) . ?
C7 C8 1.5310(17) . ?
C8 C13 1.3856(18) . ?
C8 C9 1.3915(16) . ?
C9 C10 1.3800(19) . ?
C10 C11 1.375(2) . ?
C11 C12 1.3825(19) . ?
C12 C13 1.3829(19) . ?
C14 C15 1.3831(18) . ?
C14 C19 1.3951(18) . ?
C15 C16 1.389(2) . ?
C16 C17 1.378(2) . ?
C17 C18 1.379(2) . ?
C18 C19 1.380(2) . ?
C20 C21 1.387(2) . ?
C20 C25 1.391(2) . ?
C21 C22 1.385(2) . ?
C22 C23 1.378(3) . ?
C23 C24 1.364(3) . ?
C24 C25 1.375(3) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 71375539
