#------------------------------------------------------------------------------
#$Date: 2015-01-27 21:58:39 +0200 (Tue, 27 Jan 2015) $
#$Revision: 130149 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/10/4021069.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_4021069
loop_
_publ_author_name
'Carolyn Selenski'
'Thomas R. R. Pettus'
_publ_section_title
;
 Enantioselective [4 + 2] Cycloadditions of o-Quinone Methides:
 Total Synthesis of (+)-Mimosifoliol and Formal
 Synthesis of (+)-Tolterodine
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9196
_journal_page_last               9203
_journal_paper_doi               10.1021/jo048703c
_journal_volume                  69
_journal_year                    2004
_chemical_formula_sum            'C29 H32 O6'
_chemical_formula_weight         476.55
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                101.808(4)
_cell_angle_beta                 93.818(4)
_cell_angle_gamma                113.117(4)
_cell_formula_units_Z            4
_cell_length_a                   12.389(3)
_cell_length_b                   12.719(3)
_cell_length_c                   19.197(5)
_cell_measurement_temperature    293(2)
_cell_volume                     2686.7(12)
_diffrn_ambient_temperature      293(2)
_exptl_crystal_density_diffrn    1.178
_cod_database_code               4021069
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
O1 O 0.71655(11) 0.93034(11) 0.04901(7) 0.0366(3) Uani 1 1 d . . .
O2 O 0.62026(12) 0.66388(12) 0.24981(7) 0.0388(3) Uani 1 1 d . . .
O3 O 0.49696(13) 0.54847(11) 0.31274(7) 0.0420(4) Uani 1 1 d . . .
O4 O 0.89249(11) 0.92032(11) 0.13246(7) 0.0350(3) Uani 1 1 d . . .
O5 O 0.88226(12) 1.09350(12) 0.18107(8) 0.0431(4) Uani 1 1 d . . .
O6 O 1.03116(11) 1.08032(11) 0.12222(7) 0.0382(3) Uani 1 1 d . . .
C11 C 0.77496(16) 0.85898(15) 0.14140(10) 0.0304(4) Uani 1 1 d . . .
C12 C 0.68316(16) 0.85948(15) 0.09564(9) 0.0293(4) Uani 1 1 d . . .
C13 C 0.56710(17) 0.79134(15) 0.10200(9) 0.0302(4) Uani 1 1 d . . .
H13 H 0.5047 0.7902 0.0716 0.036 Uiso 1 1 calc R . .
C14 C 0.54158(16) 0.72435(15) 0.15290(9) 0.0291(4) Uani 1 1 d . . .
C15 C 0.63553(17) 0.72713(15) 0.19794(9) 0.0310(4) Uani 1 1 d . . .
C16 C 0.75222(17) 0.79380(16) 0.19165(10) 0.0325(4) Uani 1 1 d . . .
H16 H 0.8148 0.7942 0.2215 0.039 Uiso 1 1 calc R . .
C17 C 0.62571(19) 0.92471(19) -0.00252(11) 0.0451(5) Uani 1 1 d . . .
H17A H 0.5863 0.8459 -0.0329 0.068 Uiso 1 1 calc R . .
H17B H 0.6602 0.9788 -0.0315 0.068 Uiso 1 1 calc R . .
H17C H 0.5691 0.9456 0.0219 0.068 Uiso 1 1 calc R . .
C21 C 0.33409(17) 0.58483(17) 0.08721(10) 0.0346(5) Uani 1 1 d . . .
C22 C 0.23075(19) 0.5974(2) 0.06786(13) 0.0546(6) Uani 1 1 d . . .
H22 H 0.2092 0.6493 0.0991 0.066 Uiso 1 1 calc R . .
C23 C 0.1593(2) 0.5319(3) 0.00129(17) 0.0788(10) Uani 1 1 d . . .
H23 H 0.0909 0.5416 -0.0121 0.095 Uiso 1 1 calc R . .
C24 C 0.1892(3) 0.4522(3) -0.04520(15) 0.0761(9) Uani 1 1 d . . .
H24 H 0.1405 0.4077 -0.0891 0.091 Uiso 1 1 calc R . .
C25 C 0.2905(2) 0.4400(2) -0.02584(12) 0.0581(7) Uani 1 1 d . . .
H25 H 0.3110 0.3868 -0.0567 0.070 Uiso 1 1 calc R . .
C26 C 0.36257(19) 0.50565(17) 0.03879(10) 0.0404(5) Uani 1 1 d . . .
H26 H 0.4322 0.4971 0.0506 0.049 Uiso 1 1 calc R . .
C27 C 0.41289(17) 0.65257(16) 0.15956(10) 0.0324(4) Uani 1 1 d . . .
H27 H 0.3817 0.7080 0.1833 0.039 Uiso 1 1 calc R . .
C28 C 0.40809(18) 0.56948(16) 0.20775(10) 0.0350(5) Uani 1 1 d . . .
H28A H 0.3315 0.5429 0.2239 0.042 Uiso 1 1 calc R . .
H28B H 0.4158 0.5006 0.1801 0.042 Uiso 1 1 calc R . .
C29 C 0.50481(18) 0.62891(16) 0.27177(10) 0.0352(5) Uani 1 1 d . . .
H29 H 0.4971 0.6978 0.3008 0.042 Uiso 1 1 calc R . .
C31 C 0.5160(2) 0.67285(19) 0.43182(10) 0.0422(5) Uani 1 1 d . . .
C32 C 0.3947(2) 0.6372(2) 0.42926(12) 0.0491(6) Uani 1 1 d . . .
H32 H 0.3424 0.5670 0.3972 0.059 Uiso 1 1 calc R . .
C33 C 0.3502(2) 0.7051(2) 0.47396(13) 0.0585(7) Uani 1 1 d . . .
H33 H 0.2684 0.6803 0.4717 0.070 Uiso 1 1 calc R . .
C34 C 0.4265(3) 0.8088(3) 0.52157(13) 0.0694(8) Uani 1 1 d . . .
H34 H 0.3965 0.8545 0.5514 0.083 Uiso 1 1 calc R . .
C35 C 0.5461(3) 0.8448(3) 0.52499(14) 0.0736(8) Uani 1 1 d . . .
H35 H 0.5978 0.9148 0.5575 0.088 Uiso 1 1 calc R . .
C36 C 0.5914(2) 0.7774(2) 0.48017(12) 0.0578(6) Uani 1 1 d . . .
H36 H 0.6733 0.8030 0.4827 0.069 Uiso 1 1 calc R . .
C37 C 0.5657(2) 0.59868(19) 0.38420(10) 0.0426(5) Uani 1 1 d . . .
H37 H 0.6480 0.6484 0.3810 0.051 Uiso 1 1 calc R . .
C38 C 0.5633(3) 0.4942(2) 0.41188(13) 0.0616(7) Uani 1 1 d . . .
H38A H 0.4828 0.4444 0.4143 0.092 Uiso 1 1 calc R . .
H38B H 0.6102 0.5223 0.4591 0.092 Uiso 1 1 calc R . .
H38C H 0.5954 0.4500 0.3797 0.092 Uiso 1 1 calc R . .
C41 C 0.93205(17) 1.04035(16) 0.14855(10) 0.0318(4) Uani 1 1 d . . .
C42 C 1.09226(19) 1.20721(18) 0.12538(12) 0.0473(6) Uani 1 1 d . . .
C43 C 1.0107(3) 1.2419(3) 0.0831(2) 0.1061(12) Uani 1 1 d . . .
H43A H 0.9842 1.1906 0.0353 0.159 Uiso 1 1 calc R . .
H43B H 1.0526 1.3220 0.0803 0.159 Uiso 1 1 calc R . .
H43C H 0.9432 1.2353 0.1067 0.159 Uiso 1 1 calc R . .
C44 C 1.1307(3) 1.2770(3) 0.20306(16) 0.1042(13) Uani 1 1 d . . .
H44A H 1.0622 1.2624 0.2267 0.156 Uiso 1 1 calc R . .
H44B H 1.1695 1.3597 0.2052 0.156 Uiso 1 1 calc R . .
H44C H 1.1848 1.2533 0.2268 0.156 Uiso 1 1 calc R . .
C45 C 1.1973(2) 1.2132(2) 0.08895(16) 0.0707(8) Uani 1 1 d . . .
H45A H 1.2467 1.1885 0.1161 0.106 Uiso 1 1 calc R . .
H45B H 1.2423 1.2929 0.0863 0.106 Uiso 1 1 calc R . .
H45C H 1.1700 1.1621 0.0411 0.106 Uiso 1 1 calc R . .
O7 O 0.17433(12) 0.83854(12) 0.19582(8) 0.0442(4) Uani 1 1 d . . .
O8 O 0.62271(12) 0.98130(13) 0.34825(7) 0.0442(4) Uani 1 1 d . . .
O9 O 0.80416(12) 1.12833(13) 0.39597(7) 0.0460(4) Uani 1 1 d . . .
O10 O 0.20450(12) 0.79590(11) 0.32530(7) 0.0427(4) Uani 1 1 d . . .
O11 O 0.17557(14) 0.61645(12) 0.25897(8) 0.0520(4) Uani 1 1 d . . .
O12 O 0.04722(13) 0.64899(12) 0.33019(9) 0.0553(4) Uani 1 1 d . . .
C51 C 0.30438(18) 0.85128(16) 0.29488(10) 0.0347(5) Uani 1 1 d . . .
C52 C 0.28949(17) 0.88199(16) 0.23014(10) 0.0343(5) Uani 1 1 d . . .
C53 C 0.38911(17) 0.95322(16) 0.20714(10) 0.0326(4) Uani 1 1 d . . .
H53 H 0.3802 0.9756 0.1647 0.039 Uiso 1 1 calc R . .
C54 C 0.50376(17) 0.99291(15) 0.24598(9) 0.0298(4) Uani 1 1 d . . .
C55 C 0.51517(17) 0.95441(16) 0.30762(10) 0.0329(4) Uani 1 1 d . . .
C56 C 0.41540(18) 0.88539(16) 0.33267(10) 0.0361(5) Uani 1 1 d . . .
H56 H 0.4240 0.8624 0.3749 0.043 Uiso 1 1 calc R . .
C57 C 0.1546(2) 0.8793(2) 0.13436(13) 0.0572(6) Uani 1 1 d . . .
H57A H 0.1856 0.9640 0.1476 0.086 Uiso 1 1 calc R . .
H57B H 0.0708 0.8467 0.1168 0.086 Uiso 1 1 calc R . .
H57C H 0.1942 0.8547 0.0972 0.086 Uiso 1 1 calc R . .
C61 C 0.59467(17) 1.16754(15) 0.19009(9) 0.0309(4) Uani 1 1 d . . .
C62 C 0.64865(18) 1.19702(17) 0.13165(10) 0.0368(5) Uani 1 1 d . . .
H62 H 0.6886 1.1544 0.1094 0.044 Uiso 1 1 calc R . .
C63 C 0.6435(2) 1.2900(2) 0.10606(11) 0.0482(6) Uani 1 1 d . . .
H63 H 0.6792 1.3086 0.0665 0.058 Uiso 1 1 calc R . .
C64 C 0.5857(2) 1.35457(19) 0.13902(12) 0.0512(6) Uani 1 1 d . . .
H64 H 0.5834 1.4174 0.1222 0.061 Uiso 1 1 calc R . .
C65 C 0.5312(2) 1.32576(19) 0.19696(12) 0.0491(6) Uani 1 1 d . . .
H65 H 0.4916 1.3688 0.2191 0.059 Uiso 1 1 calc R . .
C66 C 0.53544(19) 1.23309(17) 0.22203(11) 0.0394(5) Uani 1 1 d . . .
H66 H 0.4981 1.2140 0.2610 0.047 Uiso 1 1 calc R . .
C67 C 0.61360(16) 1.07738(15) 0.22433(9) 0.0299(4) Uani 1 1 d . . .
H67 H 0.6433 1.0311 0.1900 0.036 Uiso 1 1 calc R . .
C68 C 0.70878(17) 1.14368(16) 0.29120(10) 0.0340(4) Uani 1 1 d . . .
H68A H 0.7824 1.1914 0.2770 0.041 Uiso 1 1 calc R . .
H68B H 0.6842 1.1965 0.3234 0.041 Uiso 1 1 calc R . .
C69 C 0.73054(18) 1.06212(17) 0.33056(10) 0.0365(5) Uani 1 1 d . . .
H69 H 0.7684 1.0178 0.3016 0.044 Uiso 1 1 calc R . .
C71 C 0.9731(3) 1.0813(3) 0.39886(12) 0.0630(8) Uani 1 1 d . . .
C72 C 0.9821(4) 0.9826(4) 0.35782(15) 0.1156(16) Uani 1 1 d . . .
H72 H 0.9200 0.9083 0.3505 0.139 Uiso 1 1 calc R . .
C73 C 1.0821(7) 0.9950(8) 0.3283(3) 0.192(4) Uani 1 1 d . . .
H73 H 1.0853 0.9282 0.2997 0.230 Uiso 1 1 calc R . .
C74 C 1.1746(6) 1.0973(11) 0.3384(4) 0.221(6) Uani 1 1 d . . .
H74 H 1.2425 1.1023 0.3188 0.266 Uiso 1 1 calc R . .
C75 C 1.1676(4) 1.1976(7) 0.3792(3) 0.166(3) Uani 1 1 d . . .
H75 H 1.2313 1.2708 0.3862 0.199 Uiso 1 1 calc R . .
C76 C 1.0670(3) 1.1900(4) 0.40959(17) 0.0934(11) Uani 1 1 d . . .
H76 H 1.0631 1.2575 0.4369 0.112 Uiso 1 1 calc R . .
C77 C 0.8623(2) 1.0682(2) 0.42971(13) 0.0593(7) Uani 1 1 d . . .
H77 H 0.8088 0.9841 0.4190 0.071 Uiso 1 1 calc R . .
C78 C 0.8822(3) 1.1203(4) 0.50973(14) 0.1025(12) Uani 1 1 d . . .
H78A H 0.9329 1.2032 0.5206 0.154 Uiso 1 1 calc R . .
H78B H 0.9191 1.0816 0.5345 0.154 Uiso 1 1 calc R . .
H78C H 0.8072 1.1094 0.5251 0.154 Uiso 1 1 calc R . .
C81 C 0.14366(18) 0.67755(17) 0.29965(11) 0.0382(5) Uani 1 1 d . . .
C82 C -0.0371(2) 0.5232(2) 0.31680(14) 0.0594(7) Uani 1 1 d . . .
C83 C -0.1344(3) 0.5329(3) 0.3585(2) 0.1204(15) Uani 1 1 d . . .
H83A H -0.1020 0.5668 0.4088 0.181 Uiso 1 1 calc R . .
H83B H -0.1971 0.4557 0.3522 0.181 Uiso 1 1 calc R . .
H83C H -0.1657 0.5823 0.3407 0.181 Uiso 1 1 calc R . .
C84 C -0.0855(3) 0.4712(3) 0.23756(17) 0.0864(10) Uani 1 1 d . . .
H84A H -0.1171 0.5203 0.2198 0.130 Uiso 1 1 calc R . .
H84B H -0.1475 0.3934 0.2304 0.130 Uiso 1 1 calc R . .
H84C H -0.0228 0.4667 0.2120 0.130 Uiso 1 1 calc R . .
C85 C 0.0241(2) 0.4578(2) 0.34787(16) 0.0745(8) Uani 1 1 d . . .
H85A H 0.0870 0.4561 0.3216 0.112 Uiso 1 1 calc R . .
H85B H -0.0323 0.3785 0.3441 0.112 Uiso 1 1 calc R . .
H85C H 0.0568 0.4972 0.3977 0.112 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 C12 1.368(2) . ?
O1 C17 1.418(2) . ?
O2 C15 1.381(2) . ?
O2 C29 1.442(2) . ?
O3 C29 1.392(2) . ?
O3 C37 1.440(2) . ?
O4 C41 1.366(2) . ?
O4 C11 1.398(2) . ?
O5 C41 1.197(2) . ?
O6 C41 1.311(2) . ?
O6 C42 1.475(2) . ?
C11 C16 1.370(3) . ?
C11 C12 1.393(3) . ?
C12 C13 1.386(3) . ?
C13 C14 1.397(3) . ?
C14 C15 1.387(3) . ?
C14 C27 1.524(3) . ?
C15 C16 1.388(3) . ?
C21 C22 1.387(3) . ?
C21 C26 1.394(3) . ?
C21 C27 1.514(3) . ?
C22 C23 1.395(4) . ?
C23 C24 1.388(4) . ?
C24 C25 1.361(4) . ?
C25 C26 1.370(3) . ?
C27 C28 1.528(3) . ?
C28 C29 1.493(3) . ?
C31 C36 1.381(3) . ?
C31 C32 1.383(3) . ?
C31 C37 1.511(3) . ?
C32 C33 1.385(3) . ?
C33 C34 1.372(4) . ?
C34 C35 1.362(4) . ?
C35 C36 1.389(3) . ?
C37 C38 1.519(3) . ?
C42 C45 1.501(3) . ?
C42 C43 1.504(4) . ?
C42 C44 1.507(4) . ?
O7 C52 1.372(2) . ?
O7 C57 1.425(3) . ?
O8 C55 1.377(2) . ?
O8 C69 1.443(2) . ?
O9 C69 1.389(2) . ?
O9 C77 1.447(3) . ?
O10 C81 1.354(2) . ?
O10 C51 1.396(2) . ?
O11 C81 1.185(2) . ?
O12 C81 1.320(2) . ?
O12 C82 1.484(3) . ?
C51 C56 1.370(3) . ?
C51 C52 1.399(3) . ?
C52 C53 1.377(3) . ?
C53 C54 1.404(3) . ?
C54 C55 1.389(3) . ?
C54 C67 1.513(3) . ?
C55 C56 1.389(3) . ?
C61 C62 1.386(3) . ?
C61 C66 1.393(3) . ?
C61 C67 1.517(3) . ?
C62 C63 1.391(3) . ?
C63 C64 1.378(3) . ?
C64 C65 1.378(3) . ?
C65 C66 1.379(3) . ?
C67 C68 1.524(3) . ?
C68 C69 1.494(3) . ?
C71 C76 1.377(5) . ?
C71 C72 1.388(4) . ?
C71 C77 1.495(4) . ?
C72 C73 1.364(7) . ?
C73 C74 1.319(12) . ?
C74 C75 1.390(11) . ?
C75 C76 1.389(5) . ?
C77 C78 1.505(4) . ?
C82 C85 1.504(4) . ?
C82 C84 1.505(4) . ?
C82 C83 1.521(4) . ?
