#------------------------------------------------------------------------------
#$Date: 2022-09-14 23:33:16 +0300 (Wed, 14 Sep 2022) $
#$Revision: 277842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/03/4020375.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_4020375
loop_
_publ_author_name
'Hassan Sheibani'
'Paul V. Bernhardt'
'Curt Wentrup'
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5859
_journal_page_last               5861
_journal_paper_doi               10.1021/jo050428m
_journal_volume                  70
_journal_year                    2005
_chemical_formula_moiety         'C25 H19 N1 O3'
_chemical_formula_structural     'C25 H19 N O3'
_chemical_formula_sum            'C25 H19 N O3'
_chemical_formula_weight         381.41
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                111.07(2)
_cell_angle_beta                 91.51(2)
_cell_angle_gamma                106.99(2)
_cell_formula_units_Z            2
_cell_length_a                   9.7290(10)
_cell_length_b                   10.142(3)
_cell_length_c                   10.829(2)
_cell_measurement_temperature    293(2)
_cell_volume                     943.2(3)
_diffrn_ambient_temperature      293(2)
_exptl_crystal_density_diffrn    1.343
_cod_database_code               4020375
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
C1 C 0.2025(3) 0.2615(2) 0.5812(3) 0.0419(6) Uani 1 1 d . . .
C2 C 0.2090(3) 0.2037(2) 0.4299(2) 0.0388(6) Uani 1 1 d . . .
C3 C 0.0502(3) 0.1244(3) 0.3626(3) 0.0455(6) Uani 1 1 d . . .
C4 C 0.0302(3) 0.2741(3) 0.3852(3) 0.0435(6) Uani 1 1 d . . .
H4 H -0.0329 0.2781 0.3154 0.052 Uiso 1 1 calc R . .
C5 C -0.0015(3) 0.3332(3) 0.5267(3) 0.0433(6) Uani 1 1 d . . .
C6 C 0.1985(3) 0.3343(3) 0.3864(2) 0.0378(6) Uani 1 1 d . . .
H6 H 0.2435 0.4326 0.4582 0.045 Uiso 1 1 calc R . .
C7 C 0.0704(3) 0.3756(3) 0.7606(2) 0.0467(7) Uani 1 1 d . . .
H7A H 0.1051 0.3195 0.803 0.056 Uiso 1 1 calc R . .
H7B H -0.0328 0.3547 0.765 0.056 Uiso 1 1 calc R . .
C8 C 0.1469(3) 0.5394(3) 0.8379(2) 0.0412(6) Uani 1 1 d . . .
C9 C 0.2926(3) 0.6055(3) 0.8401(3) 0.0637(9) Uani 1 1 d . . .
H9 H 0.3453 0.5488 0.7881 0.076 Uiso 1 1 calc R . .
C10 C 0.3615(3) 0.7529(3) 0.9173(3) 0.0677(9) Uani 1 1 d . . .
H10 H 0.4602 0.7954 0.9173 0.081 Uiso 1 1 calc R . .
C11 C 0.2862(4) 0.8383(3) 0.9944(3) 0.0642(9) Uani 1 1 d . . .
H11 H 0.3332 0.9384 1.0476 0.077 Uiso 1 1 calc R . .
C12 C 0.1412(4) 0.7750(3) 0.9925(3) 0.0659(9) Uani 1 1 d . . .
H12 H 0.089 0.8325 1.0441 0.079 Uiso 1 1 calc R . .
C13 C 0.0722(3) 0.6276(3) 0.9152(3) 0.0513(7) Uani 1 1 d . . .
H13 H -0.0268 0.5862 0.9148 0.062 Uiso 1 1 calc R . .
C14 C 0.3230(3) 0.1303(3) 0.3933(2) 0.0443(6) Uani 1 1 d . . .
C15 C 0.2917(4) -0.0195(3) 0.3673(3) 0.0654(9) Uani 1 1 d . . .
H15 H 0.199 -0.0757 0.3721 0.078 Uiso 1 1 calc R . .
C16 C 0.3983(6) -0.0870(4) 0.3339(4) 0.0923(14) Uani 1 1 d . . .
H16 H 0.3767 -0.1882 0.3163 0.111 Uiso 1 1 calc R . .
C17 C 0.5345(6) -0.0053(6) 0.3267(4) 0.0951(14) Uani 1 1 d . . .
H17 H 0.6057 -0.0507 0.3045 0.114 Uiso 1 1 calc R . .
C18 C 0.5658(4) 0.1413(5) 0.3521(4) 0.0867(11) Uani 1 1 d . . .
H18 H 0.6589 0.1966 0.347 0.104 Uiso 1 1 calc R . .
C19 C 0.4615(3) 0.2105(4) 0.3855(3) 0.0631(8) Uani 1 1 d . . .
H19 H 0.4848 0.3118 0.4028 0.076 Uiso 1 1 calc R . .
C20 C 0.2416(3) 0.3319(3) 0.2537(2) 0.0409(6) Uani 1 1 d . . .
C21 C 0.2022(3) 0.2035(3) 0.1392(3) 0.0528(7) Uani 1 1 d . . .
H21 H 0.1507 0.1126 0.1435 0.063 Uiso 1 1 calc R . .
C22 C 0.2389(3) 0.2088(4) 0.0175(3) 0.0627(8) Uani 1 1 d . . .
H22 H 0.2127 0.1216 -0.0591 0.075 Uiso 1 1 calc R . .
C23 C 0.3135(3) 0.3421(4) 0.0103(3) 0.0668(9) Uani 1 1 d . . .
H23 H 0.3368 0.346 -0.0713 0.08 Uiso 1 1 calc R . .
C24 C 0.3537(4) 0.4693(4) 0.1230(3) 0.0683(9) Uani 1 1 d . . .
H24 H 0.4051 0.5599 0.118 0.082 Uiso 1 1 calc R . .
C25 C 0.3189(3) 0.4649(3) 0.2443(3) 0.0524(7) Uani 1 1 d . . .
H25 H 0.3478 0.5524 0.3207 0.063 Uiso 1 1 calc R . .
N1 N 0.0917(2) 0.3232(2) 0.6191(2) 0.0429(5) Uani 1 1 d . . .
O1 O 0.2869(2) 0.2567(2) 0.66104(18) 0.0550(5) Uani 1 1 d . . .
O2 O -0.0239(2) -0.0024(2) 0.3059(2) 0.0683(6) Uani 1 1 d . . .
O3 O -0.0992(2) 0.3837(2) 0.55826(19) 0.0576(5) Uani 1 1 d . . .
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
C1 O1 1.200(3) . ?
C1 N1 1.399(3) . ?
C1 C2 1.538(3) . ?
C2 C14 1.495(3) . ?
C2 C3 1.536(4) . ?
C2 C6 1.585(3) . ?
C3 O2 1.191(3) . ?
C3 C4 1.521(3) . ?
C4 C5 1.509(4) . ?
C4 C6 1.569(4) . ?
C5 O3 1.208(3) . ?
C5 N1 1.382(3) . ?
C6 C20 1.502(3) . ?
C7 N1 1.472(3) . ?
C7 C8 1.503(3) . ?
C8 C9 1.375(4) . ?
C8 C13 1.379(3) . ?
C9 C10 1.368(4) . ?
C10 C11 1.367(4) . ?
C11 C12 1.364(4) . ?
C12 C13 1.368(4) . ?
C14 C19 1.378(4) . ?
C14 C15 1.378(4) . ?
C15 C16 1.390(5) . ?
C16 C17 1.363(6) . ?
C17 C18 1.348(6) . ?
C18 C19 1.381(4) . ?
C20 C25 1.380(3) . ?
C20 C21 1.379(4) . ?
C21 C22 1.390(4) . ?
C22 C23 1.366(4) . ?
C23 C24 1.362(4) . ?
C24 C25 1.378(4) . ?
