#------------------------------------------------------------------------------
#$Date: 2016-03-21 02:18:56 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178380 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/02/4020267.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_4020267
loop_
_publ_author_name
'Yutaka Ikeuchi'
'Takeo Taguchi'
'Yuji Hanzawa'
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4354
_journal_page_last               4359
_journal_paper_doi               10.1021/jo0502293
_journal_volume                  70
_journal_year                    2005
_chemical_formula_moiety         'C23 H28 F2 O'
_chemical_formula_sum            'C23 H28 F2 O'
_chemical_formula_weight         358.45
_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                 116.287(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.5450(5)
_cell_length_b                   7.8080(3)
_cell_length_c                   20.6670(7)
_cell_measurement_temperature    100(2)
_cell_volume                     1959.69(12)
_diffrn_ambient_temperature      100(2)
_exptl_crystal_density_diffrn    1.215
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4020267
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
C1 C 0.29973(13) 0.1326(2) 0.83813(8) 0.0213(3) Uani 1 1 d . . .
H1 H 0.2795 0.2550 0.8244 0.026 Uiso 1 1 calc R . .
C2 C 0.25964(12) 0.02868(19) 0.76705(8) 0.0203(3) Uani 1 1 d . . .
H2 H 0.2942 0.0816 0.7380 0.024 Uiso 1 1 calc R . .
C3 C 0.30540(13) -0.1546(2) 0.78585(9) 0.0221(3) Uani 1 1 d . . .
H3A H 0.2830 -0.2037 0.8215 0.027 Uiso 1 1 calc R . .
H3B H 0.2726 -0.2261 0.7418 0.027 Uiso 1 1 calc R . .
C4 C 0.43163(13) -0.16171(19) 0.81689(8) 0.0206(3) Uani 1 1 d . . .
C5 C 0.48555(13) -0.00992(19) 0.86690(8) 0.0197(3) Uani 1 1 d . . .
C6 C 0.60118(13) -0.0036(2) 0.90365(8) 0.0214(3) Uani 1 1 d . . .
H6 H 0.6440 -0.0930 0.8977 0.026 Uiso 1 1 calc R . .
C7 C 0.65179(13) 0.1320(2) 0.94813(9) 0.0231(3) Uani 1 1 d . . .
C8 C 0.59496(13) 0.2636(2) 0.96132(9) 0.0246(4) Uani 1 1 d . . .
H8 H 0.6322 0.3544 0.9935 0.030 Uiso 1 1 calc R . .
C9 C 0.48082(14) 0.2566(2) 0.92524(9) 0.0238(3) Uani 1 1 d . . .
H9 H 0.4393 0.3449 0.9333 0.029 Uiso 1 1 calc R . .
C10 C 0.42473(13) 0.12401(19) 0.87736(8) 0.0199(3) Uani 1 1 d . . .
C11 C 0.24920(14) 0.0816(2) 0.88888(9) 0.0273(4) Uani 1 1 d . . .
H11A H 0.2637 -0.0399 0.9014 0.041 Uiso 1 1 calc R . .
H11B H 0.1695 0.1012 0.8647 0.041 Uiso 1 1 calc R . .
H11C H 0.2821 0.1509 0.9329 0.041 Uiso 1 1 calc R . .
C12 C 0.47049(14) -0.3304(2) 0.85903(9) 0.0255(4) Uani 1 1 d . . .
H12A H 0.5500 -0.3431 0.8757 0.038 Uiso 1 1 calc R . .
H12B H 0.4321 -0.4267 0.8275 0.038 Uiso 1 1 calc R . .
H12C H 0.4541 -0.3288 0.9007 0.038 Uiso 1 1 calc R . .
C13 C 0.46482(14) -0.1599(2) 0.75434(9) 0.0252(4) Uani 1 1 d . . .
H13A H 0.4383 -0.0541 0.7264 0.038 Uiso 1 1 calc R . .
H13B H 0.4320 -0.2588 0.7229 0.038 Uiso 1 1 calc R . .
H13C H 0.5452 -0.1656 0.7740 0.038 Uiso 1 1 calc R . .
C14 C 0.08065(13) 0.1322(2) 0.65748(9) 0.0229(3) Uani 1 1 d . . .
C15 C 0.13548(13) 0.0323(2) 0.72053(9) 0.0211(3) Uani 1 1 d . . .
C16 C 0.07072(13) -0.0728(2) 0.74190(9) 0.0230(3) Uani 1 1 d . . .
H16 H 0.1069 -0.1437 0.7831 0.028 Uiso 1 1 calc R . .
C17 C -0.04326(13) -0.0778(2) 0.70577(9) 0.0249(4) Uani 1 1 d . . .
H17 H -0.0849 -0.1497 0.7215 0.030 Uiso 1 1 calc R . .
C18 C -0.09325(13) 0.0251(2) 0.64646(9) 0.0249(4) Uani 1 1 d . . .
C19 C -0.03489(14) 0.1278(2) 0.62134(9) 0.0251(4) Uani 1 1 d . . .
H19 H -0.0730 0.1958 0.5794 0.030 Uiso 1 1 calc R . .
C20 C 0.14109(14) 0.2504(2) 0.62592(9) 0.0300(4) Uani 1 1 d . . .
C21 C 0.19032(15) 0.4114(2) 0.67385(10) 0.0310(4) Uani 1 1 d . . .
H21A H 0.2467 0.3759 0.7214 0.047 Uiso 1 1 calc R . .
H21B H 0.1317 0.4734 0.6795 0.047 Uiso 1 1 calc R . .
H21C H 0.2235 0.4864 0.6508 0.047 Uiso 1 1 calc R . .
C22 C 0.06610(15) 0.3099(3) 0.54854(11) 0.0391(5) Uani 1 1 d . . .
H22A H 0.1105 0.3677 0.5284 0.059 Uiso 1 1 calc R . .
H22B H 0.0107 0.3895 0.5493 0.059 Uiso 1 1 calc R . .
H22C H 0.0293 0.2104 0.5186 0.059 Uiso 1 1 calc R . .
C23 C 0.20913(16) 0.0145(2) 0.58341(10) 0.0329(4) Uani 1 1 d . . .
H23A H 0.1606 -0.0579 0.5956 0.049 Uiso 1 1 calc R . .
H23B H 0.2772 -0.0479 0.5934 0.049 Uiso 1 1 calc R . .
H23C H 0.1719 0.0446 0.5321 0.049 Uiso 1 1 calc R . .
F24 F 0.76482(8) 0.13684(13) 0.98151(5) 0.0287(3) Uani 1 1 d . . .
F25 F -0.20570(8) 0.02682(14) 0.60987(6) 0.0347(3) Uani 1 1 d . . .
O26 O 0.23471(10) 0.16574(15) 0.62551(6) 0.0289(3) 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 C10 1.521(2) . ?
C1 C11 1.537(2) . ?
C1 C2 1.551(2) . ?
C1 H1 1.0000 . ?
C2 C15 1.524(2) . ?
C2 C3 1.539(2) . ?
C2 H2 1.0000 . ?
C3 C4 1.538(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.529(2) . ?
C4 C12 1.538(2) . ?
C4 C13 1.545(2) . ?
C5 C10 1.406(2) . ?
C5 C6 1.407(2) . ?
C6 C7 1.370(2) . ?
C6 H6 0.9500 . ?
C7 F24 1.3732(17) . ?
C7 C8 1.382(2) . ?
C8 C9 1.389(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.401(2) . ?
C9 H9 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C19 1.405(2) . ?
C14 C15 1.415(2) . ?
C14 C20 1.556(2) . ?
C15 C16 1.407(2) . ?
C16 C17 1.386(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.368(2) . ?
C17 H17 0.9500 . ?
C18 F25 1.3681(18) . ?
C18 C19 1.379(2) . ?
C19 H19 0.9500 . ?
C20 O26 1.433(2) . ?
C20 C22 1.538(2) . ?
C20 C21 1.556(3) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 O26 1.416(2) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
