#------------------------------------------------------------------------------
#$Date: 2011-09-17 21:27:16 +0100 (Sat, 17 Sep 2011) $
#$Revision: 26029 $
#$URL: svn://www.crystallography.net/cod/cif/2/2202150.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_2202150
loop_
_publ_author_name
'Xie, Songwen'
'Hou, Yuqing'
'Meyers, Cal Y.'
'Robinson, Paul D.'
_publ_section_title
;
Lactone precursors of prostate therapy agents. II.
(+-)-5-Ethyl-endo-4-(4-methoxyphenyl)-2,2,anti-8-trimethyl-6-
oxabicyclo[3.2.1]octan-7-one, a bicyclic \g-lactone
;
_journal_name_full               'Acta Crystallographica, Section E'
_journal_page_first              o406
_journal_page_last               o407
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          'C19 H26 O3'
_chemical_formula_moiety         'C19 H26 O3'
_chemical_formula_sum            'C19 H26 O3'
_chemical_formula_weight         302.40
_chemical_melting_point          411.0(4)
_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                 91.860(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.318(2)
_cell_length_b                   7.597(3)
_cell_length_c                   12.0935(13)
_cell_measurement_temperature    296
_cell_volume                     1682.2(7)
_diffrn_ambient_temperature      296
_exptl_crystal_density_diffrn    1.194
_[local]_cod_cif_authors_sg_H-M  'P 21/c'
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '410.6-411.4' was changed to
'411.0(4)' - 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_database_code               2202150
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_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
O1 0.93628(7) 0.3563(2) 0.63097(11) 0.0632(4) Uani d . 1 . . O
O2 0.53075(6) 0.60610(17) 0.89125(10) 0.0534(3) Uani d . 1 . . O
O6 0.81709(6) 0.38375(14) 0.59134(9) 0.0392(3) Uani d . 1 . . O
C1 0.89193(9) 0.5729(2) 0.49339(13) 0.0396(4) Uani d . 1 . . C
C2 0.88546(9) 0.7544(2) 0.55194(14) 0.0442(4) Uani d . 1 . . C
C3 0.81738(9) 0.7504(2) 0.62315(14) 0.0429(4) Uani d . 1 . . C
C4 0.74931(8) 0.6614(2) 0.56946(13) 0.0367(4) Uani d . 1 . . C
C5 0.77099(8) 0.4869(2) 0.51302(12) 0.0360(4) Uani d . 1 . . C
C7 0.88847(9) 0.4283(2) 0.57833(14) 0.0420(4) Uani d . 1 . . C
C8 0.82449(9) 0.5286(2) 0.42097(13) 0.0385(4) Uani d . 1 . . C
C9 0.95324(10) 0.7874(3) 0.62595(18) 0.0647(6) Uani d . 1 . . C
C10 0.87955(12) 0.9020(2) 0.46579(18) 0.0618(5) Uani d . 1 . . C
C11 0.70693(9) 0.3694(2) 0.48118(15) 0.0457(4) Uani d . 1 . . C
C12 0.65405(11) 0.4516(3) 0.39665(17) 0.0639(6) Uani d . 1 . . C
C13 0.83925(11) 0.3767(2) 0.34180(15) 0.0531(5) Uani d . 1 . . C
C14 0.68951(8) 0.6455(2) 0.65255(13) 0.0371(4) Uani d . 1 . . C
C15 0.69860(9) 0.5449(2) 0.74874(14) 0.0438(4) Uani d . 1 . . C
C16 0.64470(9) 0.5352(2) 0.82512(14) 0.0441(4) Uani d . 1 . . C
C17 0.57972(9) 0.6252(2) 0.80858(13) 0.0395(4) Uani d . 1 . . C
C18 0.56888(9) 0.7245(2) 0.71410(14) 0.0444(4) Uani d . 1 . . C
C19 0.62381(9) 0.7334(2) 0.63789(14) 0.0432(4) Uani d . 1 . . C
C20 0.46665(11) 0.7094(3) 0.88672(19) 0.0685(6) Uani d . 1 . . C
H1 0.9367 0.5653 0.4514 0.048 Uiso calc R 1 . . H
H3a 0.8048 0.8705 0.6419 0.051 Uiso calc R 1 . . H
H3b 0.8298 0.6896 0.6917 0.051 Uiso calc R 1 . . H
H4 0.7310 0.7402 0.5108 0.044 Uiso calc R 1 . . H
H8 0.8081 0.6327 0.3793 0.046 Uiso calc R 1 . . H
H9a 0.9957 0.7904 0.5815 0.097 Uiso calc R 1 . . H
H9b 0.9583 0.6946 0.6795 0.097 Uiso calc R 1 . . H
H9c 0.9483 0.8981 0.6633 0.097 Uiso calc R 1 . . H
H10a 0.8331 0.8948 0.4269 0.093 Uiso calc R 1 . . H
H10b 0.9180 0.8897 0.4142 0.093 Uiso calc R 1 . . H
H10c 0.8838 1.0139 0.5022 0.093 Uiso calc R 1 . . H
H11a 0.6807 0.3409 0.5472 0.055 Uiso calc R 1 . . H
H11b 0.7254 0.2602 0.4513 0.055 Uiso calc R 1 . . H
H12a 0.6319 0.5537 0.4282 0.096 Uiso calc R 1 . . H
H12b 0.6169 0.3677 0.3760 0.096 Uiso calc R 1 . . H
H12c 0.6800 0.4855 0.3323 0.096 Uiso calc R 1 . . H
H13a 0.8790 0.4075 0.2956 0.080 Uiso calc R 1 . . H
H13b 0.7963 0.3543 0.2964 0.080 Uiso calc R 1 . . H
H13c 0.8518 0.2730 0.3836 0.080 Uiso calc R 1 . . H
H15 0.7419 0.4833 0.7614 0.053 Uiso calc R 1 . . H
H16 0.6521 0.4674 0.8885 0.053 Uiso calc R 1 . . H
H18 0.5252 0.7849 0.7015 0.053 Uiso calc R 1 . . H
H19 0.6161 0.8012 0.5745 0.052 Uiso calc R 1 . . H
H20a 0.4796 0.8316 0.8830 0.103 Uiso calc R 1 . . H
H20b 0.4393 0.6887 0.9518 0.103 Uiso calc R 1 . . H
H20c 0.4375 0.6780 0.8223 0.103 Uiso calc R 1 . . H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.0442(7) 0.0797(10) 0.0655(8) 0.0093(7) -0.0023(6) 0.0243(8)
O2 0.0429(7) 0.0645(8) 0.0537(7) 0.0063(6) 0.0142(6) 0.0048(6)
O6 0.0373(6) 0.0401(6) 0.0403(6) 0.0004(5) 0.0023(5) 0.0101(5)
C1 0.0382(9) 0.0418(9) 0.0393(8) -0.0025(7) 0.0085(7) 0.0018(7)
C2 0.0416(9) 0.0449(10) 0.0464(9) -0.0106(7) 0.0052(7) -0.0039(8)
C3 0.0425(9) 0.0420(9) 0.0443(9) -0.0051(7) 0.0036(7) -0.0075(7)
C4 0.0374(8) 0.0356(9) 0.0371(8) -0.0002(7) 0.0010(7) 0.0025(7)
C5 0.0387(8) 0.0333(8) 0.0359(8) -0.0022(7) -0.0022(7) 0.0047(7)
C7 0.0389(9) 0.0467(10) 0.0407(9) 0.0004(8) 0.0034(7) 0.0030(8)
C8 0.0479(9) 0.0329(8) 0.0349(8) -0.0002(7) 0.0026(7) 0.0025(7)
C9 0.0440(11) 0.0780(14) 0.0720(13) -0.0166(10) 0.0013(9) -0.0165(11)
C10 0.0754(14) 0.0426(11) 0.0683(13) -0.0161(10) 0.0129(11) 0.0041(9)
C11 0.0458(10) 0.0404(9) 0.0507(10) -0.0084(8) -0.0043(8) -0.0009(8)
C12 0.0617(12) 0.0611(13) 0.0675(13) -0.0088(10) -0.0210(10) -0.0027(10)
C13 0.0697(13) 0.0463(10) 0.0438(10) 0.0014(9) 0.0074(9) -0.0042(8)
C14 0.0360(8) 0.0380(9) 0.0372(8) 0.0005(7) -0.0006(7) 0.0007(7)
C15 0.0375(9) 0.0481(10) 0.0459(9) 0.0100(7) 0.0011(7) 0.0062(8)
C16 0.0459(10) 0.0439(10) 0.0426(9) 0.0066(8) 0.0035(8) 0.0092(8)
C17 0.0358(9) 0.0406(9) 0.0423(9) -0.0008(7) 0.0049(7) -0.0017(7)
C18 0.0348(9) 0.0493(10) 0.0491(9) 0.0078(7) -0.0014(7) 0.0013(8)
C19 0.0415(9) 0.0459(10) 0.0420(9) 0.0045(8) -0.0025(7) 0.0069(8)
C20 0.0459(11) 0.0875(16) 0.0731(13) 0.0171(11) 0.0182(10) 0.0035(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C7 . 1.507(2) no
O6 C7 . 1.3646(19) no
O6 C5 . 1.4741(18) no
O1 C7 . 1.198(2) no
O2 C17 . 1.3724(19) no
O2 C20 . 1.412(2) no
C1 C8 . 1.529(2) no
C1 C2 . 1.556(2) no
C2 C9 . 1.528(2) no
C2 C10 . 1.532(3) no
C2 C3 . 1.539(2) no
C3 C4 . 1.543(2) no
C4 C14 . 1.515(2) no
C4 C5 . 1.549(2) no
C5 C11 . 1.514(2) no
C5 C8 . 1.540(2) no
C8 C13 . 1.529(2) no
C11 C12 . 1.520(3) no
C14 C19 . 1.383(2) no
C14 C15 . 1.397(2) no
C15 C16 . 1.376(2) no
C16 C17 . 1.382(2) no
C17 C18 . 1.378(2) no
C18 C19 . 1.388(2) no
C1 H1 . 0.9800 no
C3 H3a . 0.9700 no
C3 H3b . 0.9700 no
C4 H4 . 0.9800 no
C8 H8 . 0.9800 no
C9 H9a . 0.9600 no
C9 H9b . 0.9600 no
C9 H9c . 0.9600 no
C10 H10a . 0.9600 no
C10 H10b . 0.9600 no
C10 H10c . 0.9600 no
C11 H11a . 0.9700 no
C11 H11b . 0.9700 no
C12 H12a . 0.9600 no
C12 H12b . 0.9600 no
C12 H12c . 0.9600 no
C13 H13a . 0.9600 no
C13 H13b . 0.9600 no
C13 H13c . 0.9600 no
C15 H15 . 0.9300 no
C16 H16 . 0.9300 no
C18 H18 . 0.9300 no
C19 H19 . 0.9300 no
C20 H20a . 0.9600 no
C20 H20b . 0.9600 no
C20 H20c . 0.9600 no