data_2202149
_journal_name_full  'Acta Crystallographica, Section E'
_journal_year  2003
_journal_volume  59
_journal_page_first  o403
_journal_page_last  o405
_publ_section_title
;
Lactone precursors of prostate therapy agents. I.
(+-)-anti-7-Ethyl-1-(4-methoxyphenyl)-5,5,syn-8-trimethyl-2-
oxabicyclo[2.2.2]octan-3-one, a bicyclic \d-lactone
;
loop_
_publ_author_name
  'Xie, Songwen'
  'Hou, Yuqing'
  'Meyers, Cal Y.'
  'Robinson, Paul D.'
_chemical_formula_moiety  'C19 H26 O3'
_chemical_formula_sum  'C19 H26 O3'
_chemical_formula_iupac  'C19 H26 O3'
_chemical_formula_weight  302.40
_chemical_melting_point  388-388.8
_symmetry_cell_setting  monoclinic
_symmetry_space_group_name_H-M  'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, y, -z+1/2'
  'x+1/2, y+1/2, z'
  '-x+1/2, y+1/2, -z+1/2'
  '-x, -y, -z'
  'x, -y, z-1/2'
  '-x+1/2, -y+1/2, -z'
  'x+1/2, -y+1/2, z-1/2'
_cell_length_a  32.326(4)
_cell_length_b  7.1937(12)
_cell_length_c  15.4134(19)
_cell_angle_alpha  90.00
_cell_angle_beta  104.022(9)
_cell_angle_gamma  90.00
_cell_volume  3477.5(9)
_cell_formula_units_Z  8
_cell_measurement_temperature  296
_exptl_crystal_density_diffrn  1.155
_diffrn_ambient_temperature  296
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 0.93871(5) 1.1412(2) 0.49181(13) 0.0736(5) Uani d . 1 . . O
  O2 0.88085(4) 0.97256(18) 0.43861(9) 0.0461(4) Uani d . 1 . . O
  O3 0.68514(4) 0.8026(2) 0.32443(11) 0.0666(5) Uani d . 1 . . O
  C1 0.86610(6) 0.7784(3) 0.41856(13) 0.0392(5) Uani d . 1 . . C
  C3 0.92363(6) 0.9899(3) 0.47143(14) 0.0492(5) Uani d . 1 . . C
  C4 0.94654(6) 0.8088(3) 0.47569(14) 0.0465(5) Uani d . 1 . . C
  C5 0.93708(6) 0.7320(3) 0.37866(13) 0.0461(5) Uani d . 1 . . C
  C6 0.88812(6) 0.7053(3) 0.34840(13) 0.0454(5) Uani d . 1 . . C
  C7 0.88039(6) 0.6711(3) 0.50733(13) 0.0431(5) Uani d . 1 . . C
  C8 0.92946(6) 0.6819(3) 0.53923(13) 0.0463(5) Uani d . 1 . . C
  C9 0.95205(7) 0.8732(4) 0.31840(16) 0.0709(7) Uani d . 1 . . C
  C10 0.96094(7) 0.5495(4) 0.37558(16) 0.0660(7) Uani d . 1 . . C
  C11 0.86319(7) 0.4719(3) 0.50172(15) 0.0550(6) Uani d . 1 . . C
  C12 0.87329(9) 0.3698(4) 0.59109(17) 0.0769(8) Uani d . 1 . . C
  C13 0.94435(8) 0.7514(4) 0.63569(14) 0.0714(7) Uani d . 1 . . C
  C14 0.81795(6) 0.7904(3) 0.38787(13) 0.0415(5) Uani d . 1 . . C
  C15 0.79488(6) 0.6831(3) 0.31862(14) 0.0529(6) Uani d . 1 . . C
  C16 0.75064(6) 0.6822(3) 0.29586(15) 0.0565(6) Uani d . 1 . . C
  C17 0.72884(6) 0.7921(3) 0.34206(14) 0.0479(5) Uani d . 1 . . C
  C18 0.75103(6) 0.9034(3) 0.41006(15) 0.0541(6) Uani d . 1 . . C
  C19 0.79494(6) 0.9019(3) 0.43308(14) 0.0496(5) Uani d . 1 . . C
  C20 0.66146(7) 0.6837(4) 0.2573(2) 0.0888(9) Uani d . 1 . . C
  H4 0.9773 0.8278 0.4986 0.056 Uiso calc R 1 . . H
  H6A 0.8772 0.7706 0.2925 0.054 Uiso calc R 1 . . H
  H6B 0.8817 0.5743 0.3382 0.054 Uiso calc R 1 . . H
  H7 0.8687 0.7369 0.5517 0.052 Uiso calc R 1 . . H
  H8 0.9410 0.5568 0.5361 0.056 Uiso calc R 1 . . H
  H9A 0.9822 0.8922 0.3395 0.106 Uiso calc R 1 . . H
  H9B 0.9375 0.9890 0.3197 0.106 Uiso calc R 1 . . H
  H9C 0.9459 0.8269 0.2582 0.106 Uiso calc R 1 . . H
  H10A 0.9558 0.5072 0.3148 0.099 Uiso calc R 1 . . H
  H10B 0.9510 0.4576 0.4110 0.099 Uiso calc R 1 . . H
  H10C 0.9909 0.5691 0.3990 0.099 Uiso calc R 1 . . H
  H11A 0.8325 0.4753 0.4785 0.066 Uiso calc R 1 . . H
  H11B 0.8752 0.4024 0.4597 0.066 Uiso calc R 1 . . H
  H12A 0.9036 0.3602 0.6133 0.115 Uiso calc R 1 . . H
  H12B 0.8611 0.2475 0.5830 0.115 Uiso calc R 1 . . H
  H12C 0.8615 0.4374 0.6332 0.115 Uiso calc R 1 . . H
  H13A 0.9749 0.7513 0.6532 0.107 Uiso calc R 1 . . H
  H13B 0.9334 0.6711 0.6746 0.107 Uiso calc R 1 . . H
  H13C 0.9340 0.8755 0.6397 0.107 Uiso calc R 1 . . H
  H15 0.8094 0.6092 0.2863 0.063 Uiso calc R 1 . . H
  H16 0.7359 0.6073 0.2494 0.068 Uiso calc R 1 . . H
  H18 0.7363 0.9802 0.4407 0.065 Uiso calc R 1 . . H
  H19 0.8095 0.9769 0.4797 0.060 Uiso calc R 1 . . H
  H20A 0.6691 0.7073 0.2019 0.133 Uiso calc R 1 . . H
  H20B 0.6316 0.7066 0.2500 0.133 Uiso calc R 1 . . H
  H20C 0.6677 0.5566 0.2746 0.133 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 0.0492(9) 0.0464(10) 0.1211(15) -0.0014(8) 0.0125(9) -0.0143(10)
  O2 0.0371(7) 0.0388(8) 0.0598(9) 0.0058(6) 0.0066(6) -0.0011(7)
  O3 0.0359(8) 0.0801(12) 0.0837(12) -0.0028(8) 0.0141(8) -0.0207(9)
  C1 0.0376(10) 0.0366(11) 0.0429(11) 0.0050(9) 0.0087(8) -0.0013(9)
  C3 0.0410(11) 0.0476(13) 0.0588(13) 0.0035(10) 0.0114(10) -0.0029(11)
  C4 0.0348(10) 0.0515(13) 0.0504(12) 0.0068(9) 0.0050(9) -0.0055(10)
  C5 0.0384(10) 0.0559(13) 0.0444(11) 0.0099(10) 0.0111(9) -0.0002(10)
  C6 0.0415(11) 0.0533(13) 0.0410(11) 0.0074(9) 0.0091(9) -0.0015(10)
  C7 0.0465(11) 0.0441(12) 0.0401(11) 0.0111(9) 0.0130(9) -0.0012(9)
  C8 0.0447(11) 0.0512(13) 0.0408(11) 0.0134(9) 0.0060(9) -0.0017(9)
  C9 0.0567(14) 0.095(2) 0.0650(16) -0.0025(14) 0.0215(12) 0.0108(15)
  C10 0.0558(13) 0.0811(17) 0.0585(15) 0.0255(13) 0.0089(11) -0.0162(13)
  C11 0.0589(14) 0.0470(13) 0.0602(14) 0.0067(11) 0.0166(11) 0.0046(11)
  C12 0.107(2) 0.0589(16) 0.0715(17) 0.0128(15) 0.0353(15) 0.0160(14)
  C13 0.0694(15) 0.094(2) 0.0448(13) 0.0064(15) 0.0018(11) -0.0072(13)
  C14 0.0385(10) 0.0439(12) 0.0419(11) 0.0042(9) 0.0096(9) 0.0016(9)
  C15 0.0428(11) 0.0564(14) 0.0597(14) 0.0066(10) 0.0128(10) -0.0157(11)
  C16 0.0431(12) 0.0582(14) 0.0641(14) -0.0010(10) 0.0048(11) -0.0188(12)
  C17 0.0377(11) 0.0512(13) 0.0555(13) 0.0018(10) 0.0123(9) 0.0003(11)
  C18 0.0425(12) 0.0634(14) 0.0587(14) 0.0065(11) 0.0167(10) -0.0128(12)
  C19 0.0442(12) 0.0574(14) 0.0464(12) 0.0030(10) 0.0092(9) -0.0101(10)
  C20 0.0412(13) 0.097(2) 0.121(2) -0.0087(14) 0.0064(14) -0.0348(19)
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
  C3 C4 . 1.492(3) no
  O2 C3 . 1.358(2) no
  O2 C1 . 1.484(2) no
  O1 C3 . 1.203(3) no
  O3 C17 . 1.374(2) no
  O3 C20 . 1.415(3) no
  C1 C14 . 1.516(2) no
  C1 C6 . 1.525(2) no
  C1 C7 . 1.541(3) no
  C4 C8 . 1.536(3) no
  C4 C5 . 1.554(3) no
  C5 C10 . 1.529(3) no
  C5 C9 . 1.532(3) no
  C5 C6 . 1.550(3) no
  C7 C11 . 1.532(3) no
  C7 C8 . 1.545(3) no
  C8 C13 . 1.531(3) no
  C11 C12 . 1.525(3) no
  C14 C15 . 1.380(3) no
  C14 C19 . 1.391(3) no
  C15 C16 . 1.388(3) no
  C16 C17 . 1.368(3) no
  C17 C18 . 1.375(3) no
  C18 C19 . 1.377(3) no
  C4 H4 . 0.9800 no
  C6 H6A . 0.9700 no
  C6 H6B . 0.9700 no
  C7 H7 . 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