##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section B. It has been peer reviewed under the auspices  #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary may be obtained from        #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
#           Copyright International Union of Crystallography                 #
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##############################################################################

data_almer60
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2003-11-12
_journal_date_accepted     2004-04-15
_journal_name_full     'Acta Crystallographica, Section B'
_journal_year     2004
_journal_volume     60
_journal_issue      3
_journal_page_first     300
_journal_page_last     314
_journal_paper_category     FA
_chemical_name_systematic
;
  (E)-3-(2-Ethoxyphenyl)propenoic acid
;
_chemical_name_common     'ortho-ethoxy-trans-cinnamic acid'
_chemical_formula_moiety     'C11 H12 O3'
_chemical_formula_sum     'C11 H12 O3'
_chemical_formula_weight     192.21
_chemical_melting_point     '134 - 135 \%C'
_symmetry_cell_setting     Triclinic
_symmetry_space_group_name_H-M     P-1
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     8.7336(4)
_cell_length_b     10.9590(7)
_cell_length_c     17.2709(10)
_cell_angle_alpha     91.232(4)
_cell_angle_beta     92.703(4)
_cell_angle_gamma     109.472(4)
_cell_volume     1555.53(15)
_cell_formula_units_Z     6
_cell_measurement_reflns_used     665
_cell_measurement_theta_min     2.68
_cell_measurement_theta_max     21.60
_cell_measurement_temperature     345(2)
_exptl_crystal_description     Prismic
_exptl_crystal_colour     Colourless
_exptl_crystal_size_max     1.00
_exptl_crystal_size_mid     0.34
_exptl_crystal_size_min     0.31
_exptl_crystal_density_diffrn     1.231
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     612
_exptl_absorpt_coefficient_mu     0.089
_exptl_absorpt_correction_type     None
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_exptl_special_details
;
The following alerts are triggered when using the ACTA-C CIF validation
software.
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......  0.90
PLAT063_ALERT_3_B Crystal Probably too Large for Beam Size .......  1.00 mm
REFLT03_ALERT_3_C  Reflection count < 95% complete
           From the CIF: _diffrn_reflns_theta_max           25.00
           From the CIF: _diffrn_reflns_theta_full           0.00
           From the CIF: _reflns_number_total               4937
           TEST2: Reflns within _diffrn_reflns_theta_max
           Count of symmetry unique reflns         5485
           Completeness (_total/calc)             90.01%
PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low ....  0.90
----------------
Author response: These issues are addressed in the paper associated with
this structure:
"Two crystals with different orientations were used (size: 1.0 x 0.34 x 0.33
and 1.0 x 0.34 x 0.28 mm respectively; collimator size: 0.8 mm) and a data set
at each temperature was collected for each crystal. Large crystals were used to
counteract the affect of sublimation at 375 K by allowing quick data collection
times (about 1.5 hours); smaller crystals were found to have almost disappeared
by the time the data collection run was over; alternative methods of preventing
sublimation such as coating the crystals with epoxy glue
(Hashizume et al., 2003)
or sealing in capillaries (Botoshansky et al., 1998) were avoided as it was
thought that they might interfere with the phase transition. Two crystals
in two different orientations were necessary as the heating device physically
restricted the amount of data collected on each crystal to about 60%
completeness to 25 deg Theta, for a
triclinic unit cell, while collecting two data sets on two crystals mounted in
different orientations ensured a data completeness of about 90% to 25 deg
theta."
See article for further details
PLAT305_ALERT_2_A Isolated Hydrogen Atom (Outside Bond Range ??)   H1C
PLAT355_ALERT_3_A Long    O-H Bond (0.82A)   O11B   -   H1B    ...    1.24 Ang.
PLAT355_ALERT_3_A Long    O-H Bond (0.82A)   O12A   -   H1A    ...    1.17 Ang.
PLAT417_ALERT_2_B Short Inter D-H..H-D       H1A    ..  H1A     ..    1.95 Ang.
PLAT420_ALERT_2_B D-H Without Acceptor       O11B   -   H1B    ...        ?
PLAT430_ALERT_2_B Short Inter D...A Contact  O11C   ..  O12B    ..    2.64 Ang.
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....         ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....         ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............   0.33 Ratio
---------
Author response: From article associated with this structure:
>From article "... the hydrogen bond data was obtained by
locating the carboxylic hydrogen atom positions in the difference map and then
fixing them to their parent atom. In contrast to the usual O-H bond length
of about 0.82 Å (the default for SHELX at 345 K), O-H lengths in the a'
polymorph at 345/375 K are on average about 1.21/1.28 Å long or about
46/48 % of the O...O distance (average 2.63/2.64 Å) respectively i.e.
they are almost in the middle of the hydrogen bond being shared almost equally
between two carboxylic oxygen atoms."
We chose to use located positions for the carboxylic hydrogens, rather than fix
them using AFIX in shelx, as this may more accurately describe the hydrogen
bonding
situation. The located hydrogen atoms being in the middle of the carboxylic
acid bond does cause some problems with platons builtin CIF check criteria,
which is not able to correctly connect the molecules leading to other errors
related to an incorrect calculation of the number of molecules in the unit
cell.
;
_diffrn_ambient_temperature     345(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART 1K'
_diffrn_measurement_method     'phi and omega scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     4937
_diffrn_reflns_av_R_equivalents     0.0000
_diffrn_reflns_av_sigmaI/netI     0.0294
_diffrn_reflns_theta_min     1.18
_diffrn_reflns_theta_max     25.00
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.900
_diffrn_measured_fraction_theta_full     0.900
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -12
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     0
_diffrn_reflns_limit_l_max     20
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     4937
_reflns_number_gt     2689
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1022
_refine_ls_R_factor_gt     0.0494
_refine_ls_wR_factor_gt     0.1262
_refine_ls_wR_factor_ref     0.1524
_refine_ls_goodness_of_fit_ref     1.021
_refine_ls_restrained_S_all     1.021
_refine_ls_number_reflns     4937
_refine_ls_number_parameters     386
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0807P)²+0.0096P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.162
_refine_diff_density_min     -0.122
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef     0.0085(17)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 0.0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0106 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'SMART-NT (Bruker, 1998)'
_computing_cell_refinement     'SAINT+(Bruker, 1999a)'
_computing_data_reduction     'SAINT+(Bruker, 1999a)'
_computing_structure_solution     'SHELXTL (Bruker, 1999b)'
_computing_structure_refinement     'SHELXTL (Bruker, 1999b)'
_computing_molecular_graphics
;
PLATON (Spek, 2003), SHELXTL (Bruker, 1999b),
SCHAKAL-97 (Keller, 1997) and DS ViewerPro (Accelrys, 2002)
;
_computing_publication_material     'SHELXTL (Bruker, 1999b)'
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
    C1A 1.0179(3) 0.0351(2) 0.22241(13) 0.0789(6) Uani d . 1 . . C
    C2A 1.0129(3) 0.0300(2) 0.30283(13) 0.0813(6) Uani d . 1 . . C
    C3A 1.1498(3) 0.0399(3) 0.34824(15) 0.1015(8) Uani d . 1 . . C
    H3A 1.1450 0.0370 0.4019 0.122 Uiso calc R 1 . . H
    C4A 1.2939(3) 0.0541(3) 0.31491(19) 0.1150(9) Uani d . 1 . . C
    H4A 1.3863 0.0606 0.3461 0.138 Uiso calc R 1 . . H
    C5A 1.3024(3) 0.0586(3) 0.2361(2) 0.1148(9) Uani d . 1 . . C
    H5A 1.4000 0.0675 0.2136 0.138 Uiso calc R 1 . . H
    C6A 1.1666(3) 0.0502(2) 0.19071(16) 0.1007(8) Uani d . 1 . . C
    H6A 1.1737 0.0546 0.1372 0.121 Uiso calc R 1 . . H
    C11A 0.8700(3) 0.0252(2) 0.17502(13) 0.0836(7) Uani d . 1 . . C
    H11A 0.7784 0.0199 0.2019 0.100 Uiso calc R 1 . . H
    C12A 0.8519(3) 0.0230(2) 0.09937(14) 0.0918(7) Uani d . 1 . . C
    H12A 0.9419 0.0294 0.0709 0.110 Uiso calc R 1 . . H
    C13A 0.6983(3) 0.0109(2) 0.05687(15) 0.0866(7) Uani d . 1 . . C
    C21A 0.8489(3) 0.0112(3) 0.41270(13) 0.1027(8) Uani d . 1 . . C
    H21E 0.9250 0.0890 0.4381 0.123 Uiso calc R 1 . . H
    H21F 0.8722 -0.0631 0.4328 0.123 Uiso calc R 1 . . H
    C22A 0.6795(3) 0.0018(3) 0.42765(15) 0.1280(10) Uani d . 1 . . C
    H22G 0.6576 0.0757 0.4075 0.192 Uiso calc R 1 . . H
    H22H 0.6660 -0.0005 0.4825 0.192 Uiso calc R 1 . . H
    H22I 0.6052 -0.0758 0.4026 0.192 Uiso calc R 1 . . H
    O11A 0.6952(2) 0.01020(17) -0.01537(9) 0.1090(6) Uani d . 1 . . O
    O12A 0.5726(2) 0.00053(17) 0.09525(8) 0.1068(6) Uani d . 1 . . O
    H1A 0.4692 0.0100 0.0526 0.242(19) Uiso d R 1 . . H
    O21A 0.86409(18) 0.01490(16) 0.33134(8) 0.0961(5) Uani d . 1 . . O
    C1B 0.8074(2) 0.3527(2) 0.13506(12) 0.0718(6) Uani d . 1 . . C
    C2B 0.8054(2) 0.3390(2) 0.05442(12) 0.0726(6) Uani d . 1 . . C
    C3B 0.6699(3) 0.3333(2) 0.00898(14) 0.0944(7) Uani d . 1 . . C
    H3B 0.6701 0.3246 -0.0447 0.113 Uiso calc R 1 . . H
    C4B 0.5329(3) 0.3405(3) 0.04312(17) 0.1079(9) Uani d . 1 . . C
    H4B 0.4408 0.3357 0.0122 0.129 Uiso calc R 1 . . H
    C5B 0.5317(3) 0.3547(3) 0.12155(18) 0.1101(9) Uani d . 1 . . C
    H5B 0.4397 0.3604 0.1442 0.132 Uiso calc R 1 . . H
    C6B 0.6668(3) 0.3604(2) 0.16679(15) 0.0947(7) Uani d . 1 . . C
    H6B 0.6650 0.3697 0.2203 0.114 Uiso calc R 1 . . H
    C11B 0.9519(3) 0.35932(19) 0.18293(12) 0.0738(6) Uani d . 1 . . C
    H11B 1.0441 0.3651 0.1564 0.089 Uiso calc R 1 . . H
    C12B 0.9684(3) 0.3582(2) 0.25900(12) 0.0845(7) Uani d . 1 . . C
    H12B 0.8783 0.3531 0.2870 0.101 Uiso calc R 1 . . H
    C13B 1.1174(3) 0.3643(2) 0.30209(12) 0.0803(6) Uani d . 1 . . C
    C21B 0.9511(2) 0.3152(2) -0.05662(11) 0.0817(6) Uani d . 1 . . C
    H21A 0.9373 0.3885 -0.0828 0.098 Uiso calc R 1 . . H
    H21B 0.8650 0.2372 -0.0758 0.098 Uiso calc R 1 . . H
    C22B 1.1141(3) 0.3047(2) -0.07109(13) 0.0971(8) Uani d . 1 . . C
    H22D 1.1979 0.3837 -0.0538 0.146 Uiso calc R 1 . . H
    H22E 1.1208 0.2896 -0.1256 0.146 Uiso calc R 1 . . H
    H22F 1.1279 0.2339 -0.0432 0.146 Uiso calc R 1 . . H
    O11B 1.1114(2) 0.34873(16) 0.37454(8) 0.0982(5) Uani d . 1 . . O
    H1B 1.2335 0.3478 0.4136 0.251(18) Uiso d R 1 . . H
    O12B 1.24646(19) 0.38378(16) 0.26678(8) 0.0981(5) Uani d . 1 . . O
    O21B 0.94565(16) 0.33197(15) 0.02525(7) 0.0825(5) Uani d . 1 . . O
    C1C 0.2044(2) 0.6761(2) 0.41880(12) 0.0727(6) Uani d . 1 . . C
    C2C 0.2171(2) 0.6971(2) 0.33960(12) 0.0746(6) Uani d . 1 . . C
    C3C 0.0873(3) 0.7034(2) 0.29414(14) 0.0952(7) Uani d . 1 . . C
    H3C 0.0977 0.7173 0.2414 0.114 Uiso calc R 1 . . H
    C4C -0.0581(3) 0.6893(3) 0.32632(18) 0.1069(8) Uani d . 1 . . C
    H4C -0.1459 0.6934 0.2951 0.128 Uiso calc R 1 . . H
    C5C -0.0750(3) 0.6694(2) 0.40403(18) 0.1060(9) Uani d . 1 . . C
    H5C -0.1734 0.6606 0.4257 0.127 Uiso calc R 1 . . H
    C6C 0.0540(3) 0.6626(2) 0.44922(14) 0.0922(7) Uani d . 1 . . C
    H6C 0.0418 0.6485 0.5018 0.111 Uiso calc R 1 . . H
    C11C 0.3420(3) 0.6665(2) 0.46571(12) 0.0773(6) Uani d . 1 . . C
    H11C 0.4367 0.6781 0.4400 0.093 Uiso calc R 1 . . H
    C12C 0.3496(3) 0.6434(2) 0.54027(13) 0.0857(7) Uani d . 1 . . C
    H12C 0.2573 0.6318 0.5679 0.103 Uiso calc R 1 . . H
    C13C 0.4940(3) 0.6350(2) 0.58137(13) 0.0854(7) Uani d . 1 . . C
    C21C 0.3828(3) 0.7136(3) 0.23053(12) 0.0958(8) Uani d . 1 . . C
    H21C 0.3737 0.7938 0.2116 0.115 Uiso calc R 1 . . H
    H21D 0.2983 0.6417 0.2040 0.115 Uiso calc R 1 . . H
    C22C 0.5453(3) 0.7060(3) 0.21584(13) 0.1112(9) Uani d . 1 . . C
    H22A 0.6278 0.7765 0.2434 0.167 Uiso calc R 1 . . H
    H22B 0.5615 0.7114 0.1613 0.167 Uiso calc R 1 . . H
    H22C 0.5518 0.6253 0.2334 0.167 Uiso calc R 1 . . H
    O11C 0.4853(2) 0.60726(18) 0.65238(9) 0.1148(6) Uani d . 1 . . O
    H1C 0.6111 0.6123 0.6892 0.217(14) Uiso d R 1 . . H
    O12C 0.62491(19) 0.65652(16) 0.54689(8) 0.1010(5) Uani d . 1 . . O
    O21C 0.36550(16) 0.70875(16) 0.31198(8) 0.0909(5) Uani d . 1 . . O
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
    C1A C2A . 1.393(3) ?
    C1A C6A . 1.394(3) ?
    C1A C11A . 1.467(3) ?
    C2A O21A . 1.371(2) ?
    C2A C3A . 1.371(3) ?
    C3A C4A . 1.371(3) ?
    C3A H3A . 0.9300 ?
    C4A C5A . 1.367(3) ?
    C4A H4A . 0.9300 ?
    C5A C6A . 1.366(3) ?
    C5A H5A . 0.9300 ?
    C6A H6A . 0.9300 ?
    C11A C12A . 1.307(3) ?
    C11A H11A . 0.9300 ?
    C12A C13A . 1.463(3) ?
    C12A H12A . 0.9300 ?
    C13A O11A . 1.246(2) ?
    C13A O12A . 1.283(2) ?
    C21A O21A . 1.418(2) ?
    C21A C22A . 1.484(3) ?
    C21A H21E . 0.9700 ?
    C21A H21F . 0.9700 ?
    C22A H22G . 0.9600 ?
    C22A H22H . 0.9600 ?
    C22A H22I . 0.9600 ?
    O12A H1A . 1.1705 ?
    C1B C6B . 1.394(3) ?
    C1B C2B . 1.396(3) ?
    C1B C11B . 1.456(3) ?
    C2B O21B . 1.371(2) ?
    C2B C3B . 1.371(3) ?
    C3B C4B . 1.383(3) ?
    C3B H3B . 0.9300 ?
    C4B C5B . 1.361(3) ?
    C4B H4B . 0.9300 ?
    C5B C6B . 1.367(3) ?
    C5B H5B . 0.9300 ?
    C6B H6B . 0.9300 ?
    C11B C12B . 1.316(3) ?
    C11B H11B . 0.9300 ?
    C12B C13B . 1.449(3) ?
    C12B H12B . 0.9300 ?
    C13B O12B . 1.264(2) ?
    C13B O11B . 1.268(2) ?
    C21B O21B . 1.427(2) ?
    C21B C22B . 1.498(3) ?
    C21B H21A . 0.9700 ?
    C21B H21B . 0.9700 ?
    C22B H22D . 0.9600 ?
    C22B H22E . 0.9600 ?
    C22B H22F . 0.9600 ?
    O11B H1B . 1.2377 ?
    C1C C2C . 1.395(3) ?
    C1C C6C . 1.400(3) ?
    C1C C11C . 1.452(3) ?
    C2C O21C . 1.369(2) ?
    C2C C3C . 1.370(3) ?
    C3C C4C . 1.373(3) ?
    C3C H3C . 0.9300 ?
    C4C C5C . 1.371(3) ?
    C4C H4C . 0.9300 ?
    C5C C6C . 1.364(3) ?
    C5C H5C . 0.9300 ?
    C6C H6C . 0.9300 ?
    C11C C12C . 1.321(3) ?
    C11C H11C . 0.9300 ?
    C12C C13C . 1.448(3) ?
    C12C H12C . 0.9300 ?
    C13C O12C . 1.268(2) ?
    C13C O11C . 1.269(2) ?
    C21C O21C . 1.422(2) ?
    C21C C22C . 1.482(3) ?
    C21C H21C . 0.9700 ?
    C21C H21D . 0.9700 ?
    C22C H22A . 0.9600 ?
    C22C H22B . 0.9600 ?
    C22C H22C . 0.9600 ?
    O11C H1C . 1.2278 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C2A C1A C6A . . 117.3(2) ?
    C2A C1A C11A . . 119.7(2) ?
    C6A C1A C11A . . 122.9(2) ?
    O21A C2A C3A . . 124.0(2) ?
    O21A C2A C1A . . 115.3(2) ?
    C3A C2A C1A . . 120.7(2) ?
    C2A C3A C4A . . 120.3(2) ?
    C2A C3A H3A . . 119.9 ?
    C4A C3A H3A . . 119.9 ?
    C5A C4A C3A . . 120.3(3) ?
    C5A C4A H4A . . 119.8 ?
    C3A C4A H4A . . 119.8 ?
    C6A C5A C4A . . 119.6(2) ?
    C6A C5A H5A . . 120.2 ?
    C4A C5A H5A . . 120.2 ?
    C5A C6A C1A . . 121.7(2) ?
    C5A C6A H6A . . 119.1 ?
    C1A C6A H6A . . 119.1 ?
    C12A C11A C1A . . 127.6(2) ?
    C12A C11A H11A . . 116.2 ?
    C1A C11A H11A . . 116.2 ?
    C11A C12A C13A . . 123.8(2) ?
    C11A C12A H12A . . 118.1 ?
    C13A C12A H12A . . 118.1 ?
    O11A C13A O12A . . 122.8(2) ?
    O11A C13A C12A . . 118.3(2) ?
    O12A C13A C12A . . 118.9(2) ?
    O21A C21A C22A . . 107.8(2) ?
    O21A C21A H21E . . 110.2 ?
    C22A C21A H21E . . 110.2 ?
    O21A C21A H21F . . 110.2 ?
    C22A C21A H21F . . 110.2 ?
    H21E C21A H21F . . 108.5 ?
    C21A C22A H22G . . 109.5 ?
    C21A C22A H22H . . 109.5 ?
    H22G C22A H22H . . 109.5 ?
    C21A C22A H22I . . 109.5 ?
    H22G C22A H22I . . 109.5 ?
    H22H C22A H22I . . 109.5 ?
    C13A O12A H1A . . 108.7 ?
    C2A O21A C21A . . 118.96(18) ?
    C6B C1B C2B . . 117.2(2) ?
    C6B C1B C11B . . 122.2(2) ?
    C2B C1B C11B . . 120.53(18) ?
    O21B C2B C3B . . 123.55(19) ?
    O21B C2B C1B . . 115.65(18) ?
    C3B C2B C1B . . 120.81(19) ?
    C2B C3B C4B . . 119.9(2) ?
    C2B C3B H3B . . 120.1 ?
    C4B C3B H3B . . 120.1 ?
    C5B C4B C3B . . 120.6(2) ?
    C5B C4B H4B . . 119.7 ?
    C3B C4B H4B . . 119.7 ?
    C4B C5B C6B . . 119.5(2) ?
    C4B C5B H5B . . 120.3 ?
    C6B C5B H5B . . 120.3 ?
    C5B C6B C1B . . 122.0(2) ?
    C5B C6B H6B . . 119.0 ?
    C1B C6B H6B . . 119.0 ?
    C12B C11B C1B . . 128.2(2) ?
    C12B C11B H11B . . 115.9 ?
    C1B C11B H11B . . 115.9 ?
    C11B C12B C13B . . 124.5(2) ?
    C11B C12B H12B . . 117.8 ?
    C13B C12B H12B . . 117.8 ?
    O12B C13B O11B . . 122.7(2) ?
    O12B C13B C12B . . 119.60(19) ?
    O11B C13B C12B . . 117.7(2) ?
    O21B C21B C22B . . 106.92(16) ?
    O21B C21B H21A . . 110.3 ?
    C22B C21B H21A . . 110.3 ?
    O21B C21B H21B . . 110.3 ?
    C22B C21B H21B . . 110.3 ?
    H21A C21B H21B . . 108.6 ?
    C21B C22B H22D . . 109.5 ?
    C21B C22B H22E . . 109.5 ?
    H22D C22B H22E . . 109.5 ?
    C21B C22B H22F . . 109.5 ?
    H22D C22B H22F . . 109.5 ?
    H22E C22B H22F . . 109.5 ?
    C13B O11B H1B . . 120.3 ?
    C2B O21B C21B . . 118.69(15) ?
    C2C C1C C6C . . 117.0(2) ?
    C2C C1C C11C . . 120.26(18) ?
    C6C C1C C11C . . 122.7(2) ?
    O21C C2C C3C . . 123.8(2) ?
    O21C C2C C1C . . 115.22(19) ?
    C3C C2C C1C . . 121.02(19) ?
    C2C C3C C4C . . 120.1(2) ?
    C2C C3C H3C . . 120.0 ?
    C4C C3C H3C . . 120.0 ?
    C5C C4C C3C . . 120.6(2) ?
    C5C C4C H4C . . 119.7 ?
    C3C C4C H4C . . 119.7 ?
    C6C C5C C4C . . 119.3(2) ?
    C6C C5C H5C . . 120.3 ?
    C4C C5C H5C . . 120.3 ?
    C5C C6C C1C . . 122.0(2) ?
    C5C C6C H6C . . 119.0 ?
    C1C C6C H6C . . 119.0 ?
    C12C C11C C1C . . 128.2(2) ?
    C12C C11C H11C . . 115.9 ?
    C1C C11C H11C . . 115.9 ?
    C11C C12C C13C . . 123.6(2) ?
    C11C C12C H12C . . 118.2 ?
    C13C C12C H12C . . 118.2 ?
    O12C C13C O11C . . 121.7(2) ?
    O12C C13C C12C . . 120.2(2) ?
    O11C C13C C12C . . 118.0(2) ?
    O21C C21C C22C . . 107.66(17) ?
    O21C C21C H21C . . 110.2 ?
    C22C C21C H21C . . 110.2 ?
    O21C C21C H21D . . 110.2 ?
    C22C C21C H21D . . 110.2 ?
    H21C C21C H21D . . 108.5 ?
    C21C C22C H22A . . 109.5 ?
    C21C C22C H22B . . 109.5 ?
    H22A C22C H22B . . 109.5 ?
    C21C C22C H22C . . 109.5 ?
    H22A C22C H22C . . 109.5 ?
    H22B C22C H22C . . 109.5 ?
    C13C O11C H1C . . 118.0 ?
    C2C O21C C21C . . 118.80(16) ?
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C6A C1A C2A O21A . . . . -179.91(18) ?
    C11A C1A C2A O21A . . . . 0.3(3) ?
    C6A C1A C2A C3A . . . . 0.2(3) ?
    C11A C1A C2A C3A . . . . -179.6(2) ?
    O21A C2A C3A C4A . . . . 179.6(2) ?
    C1A C2A C3A C4A . . . . -0.5(4) ?
    C2A C3A C4A C5A . . . . 0.1(4) ?
    C3A C4A C5A C6A . . . . 0.6(4) ?
    C4A C5A C6A C1A . . . . -0.9(4) ?
    C2A C1A C6A C5A . . . . 0.5(4) ?
    C11A C1A C6A C5A . . . . -179.7(2) ?
    C2A C1A C11A C12A . . . . -177.0(2) ?
    C6A C1A C11A C12A . . . . 3.2(4) ?
    C1A C11A C12A C13A . . . . 179.1(2) ?
    C11A C12A C13A O11A . . . . 179.8(2) ?
    C11A C12A C13A O12A . . . . -0.7(4) ?
    C3A C2A O21A C21A . . . . 1.1(3) ?
    C1A C2A O21A C21A . . . . -178.81(19) ?
    C22A C21A O21A C2A . . . . 176.8(2) ?
    C6B C1B C2B O21B . . . . 179.90(18) ?
    C11B C1B C2B O21B . . . . 0.3(3) ?
    C6B C1B C2B C3B . . . . -0.1(3) ?
    C11B C1B C2B C3B . . . . -179.7(2) ?
    O21B C2B C3B C4B . . . . 179.7(2) ?
    C1B C2B C3B C4B . . . . -0.3(3) ?
    C2B C3B C4B C5B . . . . 0.7(4) ?
    C3B C4B C5B C6B . . . . -0.7(4) ?
    C4B C5B C6B C1B . . . . 0.3(4) ?
    C2B C1B C6B C5B . . . . 0.1(4) ?
    C11B C1B C6B C5B . . . . 179.7(2) ?
    C6B C1B C11B C12B . . . . 8.3(4) ?
    C2B C1B C11B C12B . . . . -172.1(2) ?
    C1B C11B C12B C13B . . . . 179.6(2) ?
    C11B C12B C13B O12B . . . . 6.8(3) ?
    C11B C12B C13B O11B . . . . -172.8(2) ?
    C3B C2B O21B C21B . . . . -1.3(3) ?
    C1B C2B O21B C21B . . . . 178.70(17) ?
    C22B C21B O21B C2B . . . . -177.41(17) ?
    C6C C1C C2C O21C . . . . -179.48(17) ?
    C11C C1C C2C O21C . . . . -0.7(3) ?
    C6C C1C C2C C3C . . . . -0.3(3) ?
    C11C C1C C2C C3C . . . . 178.5(2) ?
    O21C C2C C3C C4C . . . . 179.3(2) ?
    C1C C2C C3C C4C . . . . 0.2(4) ?
    C2C C3C C4C C5C . . . . 0.3(4) ?
    C3C C4C C5C C6C . . . . -0.5(4) ?
    C4C C5C C6C C1C . . . . 0.4(4) ?
    C2C C1C C6C C5C . . . . 0.0(3) ?
    C11C C1C C6C C5C . . . . -178.7(2) ?
    C2C C1C C11C C12C . . . . -177.9(2) ?
    C6C C1C C11C C12C . . . . 0.8(4) ?
    C1C C11C C12C C13C . . . . 179.6(2) ?
    C11C C12C C13C O12C . . . . 3.6(4) ?
    C11C C12C C13C O11C . . . . -177.3(2) ?
    C3C C2C O21C C21C . . . . -7.1(3) ?
    C1C C2C O21C C21C . . . . 172.03(18) ?
    C22C C21C O21C C2C . . . . -171.53(19) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    O11C H1C O12B 2_766 1.23 1.41 2.642(2) 178.4
    O11B H1B O12C 2_766 1.24 1.40 2.635(2) 175.9
    O12A H1A O11A 2_655 1.17 1.49 2.626(3) 161.2
data_almer80
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2003-11-12
_journal_date_accepted     2004-04-15
_journal_name_full     'Acta Crystallographica, Section B'
_journal_year     2004
_journal_volume     60
_journal_issue      3
_journal_page_first     300
_journal_page_last     314
_journal_paper_category     FA
_chemical_name_systematic
;
 (E)-3-(2-Ethoxyphenyl)propenoic acid
;
_chemical_name_common     'ortho-ethoxy-trans-cinnamic acid'
_chemical_formula_moiety     'C11 H12 O3'
_chemical_formula_sum     'C11 H12 O3'
_chemical_formula_weight     192.21
_chemical_melting_point     ?
_symmetry_cell_setting     Triclinic
_symmetry_space_group_name_H-M     P-1
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     8.7373(5)
_cell_length_b     11.0167(8)
_cell_length_c     17.2950(10)
_cell_angle_alpha     91.187(4)
_cell_angle_beta     92.775(5)
_cell_angle_gamma     108.938(4)
_cell_volume     1571.62(17)
_cell_formula_units_Z     6
_cell_measurement_reflns_used     797
_cell_measurement_theta_min     2.25
_cell_measurement_theta_max     20.89
_cell_measurement_temperature     375(2)
_exptl_crystal_description     Prismic
_exptl_crystal_colour     Colourless
_exptl_crystal_size_max     1.00
_exptl_crystal_size_mid     0.34
_exptl_crystal_size_min     0.31
_exptl_crystal_density_diffrn     1.218
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     612
_exptl_absorpt_coefficient_mu     0.088
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_exptl_special_details
;
The following alerts are triggered when using the ACTA-C CIF validation
software.
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......       0.89
REFLT03_ALERT_3_B  Reflection count < 90% complete (theta max?)
           From the CIF: _diffrn_reflns_theta_max           25.00
           From the CIF: _diffrn_reflns_theta_full           0.00
           From the CIF: _reflns_number_total               4947
           TEST2: Reflns within _diffrn_reflns_theta_max
           Count of symmetry unique reflns         5534
           Completeness (_total/calc)             89.39%
PLAT022_ALERT_3_B Ratio Unique / Expected Reflections too Low ....     0.89
PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low ....     39 Perc.
PLAT063_ALERT_3_B Crystal Probably too Large for Beam Size .......     1.00 mm
----------
Author response: These issues are addressed in the paper associated with
this structure:
"Two crystals with different orientations were used (size: 1.0 x 0.34 x 0.33
and 1.0 x 0.34 x 0.28 mm respectively; collimator size: 0.8 mm) and a data set
at each temperature was collected for each crystal. Large crystals were used to
counteract the affect of sublimation at 375 K by allowing quick data collection
times (about 1.5 hours); smaller crystals were found to have almost disappeared
by the time the data collection run was over; alternative methods of preventing
sublimation such as coating the crystals with epoxy glue
(Hashizume et al., 2003)
or sealing in capillaries (Botoshansky et al., 1998) were avoided as it was
thought that they might interfere with the phase transition. Two crystals
in two different orientations were necessary as the heating device physically
restricted the amount of data collected on each crystal to about 60%
completeness to 25 deg Theta, for a
triclinic unit cell, while collecting two data sets on two crystals mounted in
different orientations ensured a data completeness of about 90% to 25 deg
theta."
See article for further details
PLAT305_ALERT_2_A Isolated Hydrogen Atom (Outside Bond Range ??)          H1C
PLAT355_ALERT_3_A Long    O-H Bond (0.82A)   O12B   -   H1B    ...    1.31 Ang.
PLAT355_ALERT_3_A Long    O-H Bond (0.82A)   O12A   -   H1A    ...    1.26 Ang.
PLAT772_ALERT_2_A Suspect O-H Bond in CIF:      O12B   -H1B     ..    1.31 Ang.
PLAT420_ALERT_2_B D-H Without Acceptor       O12A   -   H1A    ...          ?
PLAT420_ALERT_2_B D-H Without Acceptor       O12B   -   H1B    ...          ?
PLAT430_ALERT_2_B Short Inter D...A Contact  O11B   ..  O12C    ..    2.64 Ang.
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
---------
Author response: From article associated with this structure:
>From article "... the hydrogen bond data was obtained by
locating the carboxylic hydrogen atom positions in the difference map and then
fixing them to their parent atom. In contrast to the usual O-H bond length
of about 0.82 Å (the default for SHELX at 345 K), O-H lengths in the a'
polymorph at 345/375 K are on average about 1.21/1.28 Å long or about
46/48 % of the O...O distance (average 2.63/2.64 Å) respectively i.e.
they are almost in the middle of the hydrogen bond being shared almost equally
between two carboxylic oxygen atoms."
We chose to use located positions for the carboxylic hydrogens, rather than fix
them using AFIX in shelx, as this may more accurately describe the hydrogen
bonding
situation. The located hydrogen atoms being in the middle of the carboxylic
acid bond does cause some problems with platons builtin CIF check criteria,
which is not able to correctly connect the molecules leading to other errors
related to an incorrect calculation of the number of molecules in the unit cell.
;
_diffrn_ambient_temperature     375(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART 1K'
_diffrn_measurement_method     'phi and omega scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     4947
_diffrn_reflns_av_R_equivalents     0.0000
_diffrn_reflns_av_sigmaI/netI     0.0592
_diffrn_reflns_theta_min     1.18
_diffrn_reflns_theta_max     25.00
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.894
_diffrn_measured_fraction_theta_full     0.894
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -12
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     0
_diffrn_reflns_limit_l_max     20
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     4947
_reflns_number_gt     1906
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1554
_refine_ls_R_factor_gt     0.0492
_refine_ls_wR_factor_gt     0.1169
_refine_ls_wR_factor_ref     0.1569
_refine_ls_goodness_of_fit_ref     0.876
_refine_ls_restrained_S_all     0.876
_refine_ls_number_reflns     4947
_refine_ls_number_parameters     386
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0788P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.150
_refine_diff_density_min     -0.112
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef     0.0062(13)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 0.0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0106 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'SMART-NT (Bruker, 1998)'
_computing_cell_refinement     'SAINT+(Bruker, 1999a)'
_computing_data_reduction     'SAINT+(Bruker, 1999a)'
_computing_structure_solution     'SHELXTL (Bruker, 1999b)'
_computing_structure_refinement     'SHELXTL (Bruker, 1999b)'
_computing_molecular_graphics
;
PLATON (Spek, 2003), SHELXTL (Bruker, 1999b),
SCHAKAL-97 (Keller, 1997) and DS ViewerPro (Accelrys, 2002)
;
_computing_publication_material     'SHELXTL (Bruker, 1999b)'
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
    C1A 1.0173(4) 0.0345(3) 0.22231(19) 0.0918(8) Uani d . 1 . . C
    C2A 1.0123(4) 0.0293(3) 0.30236(19) 0.0950(9) Uani d . 1 . . C
    C3A 1.1485(5) 0.0389(3) 0.34807(19) 0.1192(11) Uani d . 1 . . C
    H3A 1.1434 0.0352 0.4016 0.143 Uiso calc R 1 . . H
    C4A 1.2923(5) 0.0541(3) 0.3147(3) 0.1342(13) Uani d . 1 . . C
    H4A 1.3845 0.0606 0.3459 0.161 Uiso calc R 1 . . H
    C5A 1.3023(5) 0.0598(3) 0.2362(3) 0.1317(13) Uani d . 1 . . C
    H5A 1.4004 0.0705 0.2140 0.158 Uiso calc R 1 . . H
    C6A 1.1658(5) 0.0497(3) 0.1908(2) 0.1167(11) Uani d . 1 . . C
    H6A 1.1724 0.0530 0.1373 0.140 Uiso calc R 1 . . H
    C11A 0.8693(4) 0.0251(3) 0.17491(18) 0.0988(10) Uani d . 1 . . C
    H11A 0.7778 0.0199 0.2017 0.119 Uiso calc R 1 . . H
    C12A 0.8523(5) 0.0233(3) 0.1006(2) 0.1088(10) Uani d . 1 . . C
    H12A 0.9425 0.0304 0.0723 0.131 Uiso calc R 1 . . H
    C13A 0.6961(5) 0.0104(3) 0.0575(2) 0.1000(10) Uani d . 1 . . C
    C21A 0.8482(4) 0.0113(3) 0.41231(17) 0.1272(11) Uani d . 1 . . C
    H21E 0.9225 0.0890 0.4375 0.153 Uiso calc R 1 . . H
    H21F 0.8736 -0.0617 0.4328 0.153 Uiso calc R 1 . . H
    C22A 0.6799(4) 0.0007(4) 0.42699(18) 0.1505(14) Uani d . 1 . . C
    H22G 0.6552 0.0724 0.4056 0.226 Uiso calc R 1 . . H
    H22H 0.6671 0.0004 0.4818 0.226 Uiso calc R 1 . . H
    H22I 0.6075 -0.0777 0.4031 0.226 Uiso calc R 1 . . H
    O11A 0.6956(3) 0.0099(2) -0.01446(12) 0.1277(8) Uani d . 1 . . O
    O12A 0.5719(3) 0.0006(2) 0.09493(11) 0.1222(8) Uani d . 1 . . O
    H1A 0.4401 0.0007 0.0614 0.25(2) Uiso d R 1 . . H
    O21A 0.8640(2) 0.0145(2) 0.33072(11) 0.1139(7) Uani d . 1 . . O
    C1B 0.8087(3) 0.3534(3) 0.13578(17) 0.0841(8) Uani d . 1 . . C
    C2B 0.8061(3) 0.3390(2) 0.05543(17) 0.0844(8) Uani d . 1 . . C
    C3B 0.6716(4) 0.3333(3) 0.00966(18) 0.1099(10) Uani d . 1 . . C
    H3B 0.6723 0.3244 -0.0439 0.132 Uiso calc R 1 . . H
    C4B 0.5353(4) 0.3409(3) 0.0433(2) 0.1279(12) Uani d . 1 . . C
    H4B 0.4437 0.3365 0.0122 0.154 Uiso calc R 1 . . H
    C5B 0.5328(4) 0.3548(3) 0.1219(3) 0.1298(12) Uani d . 1 . . C
    H5B 0.4404 0.3600 0.1442 0.156 Uiso calc R 1 . . H
    C6B 0.6677(4) 0.3611(3) 0.16708(19) 0.1104(10) Uani d . 1 . . C
    H6B 0.6657 0.3708 0.2205 0.132 Uiso calc R 1 . . H
    C11B 0.9523(3) 0.3591(2) 0.18385(16) 0.0854(8) Uani d . 1 . . C
    H11B 1.0443 0.3642 0.1574 0.103 Uiso calc R 1 . . H
    C12B 0.9690(4) 0.3580(3) 0.25923(17) 0.0977(9) Uani d . 1 . . C
    H12B 0.8789 0.3525 0.2872 0.117 Uiso calc R 1 . . H
    C13B 1.1196(4) 0.3646(3) 0.30273(17) 0.0923(9) Uani d . 1 . . C
    C21B 0.9524(3) 0.3149(3) -0.05520(14) 0.0963(9) Uani d . 1 . . C
    H21A 0.9373 0.3875 -0.0815 0.116 Uiso calc R 1 . . H
    H21B 0.8675 0.2375 -0.0743 0.116 Uiso calc R 1 . . H
    C22B 1.1154(3) 0.3049(3) -0.06990(16) 0.1147(11) Uani d . 1 . . C
    H22D 1.1984 0.3826 -0.0517 0.172 Uiso calc R 1 . . H
    H22E 1.1229 0.2920 -0.1245 0.172 Uiso calc R 1 . . H
    H22F 1.1296 0.2335 -0.0430 0.172 Uiso calc R 1 . . H
    O11B 1.1124(2) 0.34918(19) 0.37500(11) 0.1127(7) Uani d . 1 . . O
    O12B 1.2469(3) 0.38339(19) 0.26725(10) 0.1123(7) Uani d . 1 . . O
    H1B 1.3781 0.3768 0.3049 0.27(2) Uiso d R 1 . . H
    O21B 0.9463(2) 0.33174(18) 0.02649(10) 0.0960(6) Uani d . 1 . . O
    C1C 0.2034(3) 0.6762(2) 0.41845(17) 0.0830(8) Uani d . 1 . . C
    C2C 0.2154(4) 0.6967(3) 0.33951(17) 0.0885(8) Uani d . 1 . . C
    C3C 0.0860(4) 0.7036(3) 0.29377(18) 0.1111(10) Uani d . 1 . . C
    H3C 0.0964 0.7178 0.2412 0.133 Uiso calc R 1 . . H
    C4C -0.0592(4) 0.6896(3) 0.3261(3) 0.1266(12) Uani d . 1 . . C
    H4C -0.1471 0.6943 0.2952 0.152 Uiso calc R 1 . . H
    C5C -0.0753(4) 0.6686(3) 0.4034(3) 0.1223(12) Uani d . 1 . . C
    H5C -0.1739 0.6587 0.4250 0.147 Uiso calc R 1 . . H
    C6C 0.0539(4) 0.6624(3) 0.44855(18) 0.1069(10) Uani d . 1 . . C
    H6C 0.0419 0.6486 0.5011 0.128 Uiso calc R 1 . . H
    C11C 0.3410(4) 0.6665(3) 0.46511(16) 0.0891(8) Uani d . 1 . . C
    H11C 0.4356 0.6781 0.4395 0.107 Uiso calc R 1 . . H
    C12C 0.3486(4) 0.6433(3) 0.53937(17) 0.0999(9) Uani d . 1 . . C
    H12C 0.2561 0.6314 0.5667 0.120 Uiso calc R 1 . . H
    C13C 0.4941(4) 0.6352(3) 0.58122(18) 0.0996(9) Uani d . 1 . . C
    C21C 0.3819(3) 0.7144(3) 0.23043(15) 0.1158(11) Uani d . 1 . . C
    H21C 0.3726 0.7942 0.2117 0.139 Uiso calc R 1 . . H
    H21D 0.2981 0.6435 0.2036 0.139 Uiso calc R 1 . . H
    C22C 0.5435(4) 0.7062(3) 0.21622(17) 0.1325(12) Uani d . 1 . . C
    H22A 0.6254 0.7781 0.2417 0.199 Uiso calc R 1 . . H
    H22B 0.5579 0.7072 0.1615 0.199 Uiso calc R 1 . . H
    H22C 0.5522 0.6279 0.2362 0.199 Uiso calc R 1 . . H
    O11C 0.4849(2) 0.6081(2) 0.65176(12) 0.1326(9) Uani d . 1 . . O
    O12C 0.6235(3) 0.6569(2) 0.54658(10) 0.1160(7) Uani d . 1 . . O
    H1C 0.7462 0.6440 0.5835 0.201(15) Uiso d R 1 . . H
    O21C 0.3641(2) 0.70890(19) 0.31218(10) 0.1068(7) Uani d . 1 . . O
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
    C1A C2A . 1.389(3) ?
    C1A C6A . 1.394(4) ?
    C1A C11A . 1.470(4) ?
    C2A O21A . 1.368(3) ?
    C2A C3A . 1.370(4) ?
    C3A C4A . 1.371(4) ?
    C3A H3A . 0.9300 ?
    C4A C5A . 1.366(4) ?
    C4A H4A . 0.9300 ?
    C5A C6A . 1.367(4) ?
    C5A H5A . 0.9300 ?
    C6A H6A . 0.9300 ?
    C11A C12A . 1.285(3) ?
    C11A H11A . 0.9300 ?
    C12A C13A . 1.487(4) ?
    C12A H12A . 0.9300 ?
    C13A O11A . 1.244(3) ?
    C13A O12A . 1.266(3) ?
    C21A O21A . 1.425(3) ?
    C21A C22A . 1.472(4) ?
    C21A H21E . 0.9700 ?
    C21A H21F . 0.9700 ?
    C22A H22G . 0.9600 ?
    C22A H22H . 0.9600 ?
    C22A H22I . 0.9600 ?
    O12A H1A . 1.2645 ?
    C1B C2B . 1.394(3) ?
    C1B C6B . 1.396(3) ?
    C1B C11B . 1.454(3) ?
    C2B C3B . 1.368(3) ?
    C2B O21B . 1.371(3) ?
    C3B C4B . 1.376(3) ?
    C3B H3B . 0.9300 ?
    C4B C5B . 1.366(4) ?
    C4B H4B . 0.9300 ?
    C5B C6B . 1.364(4) ?
    C5B H5B . 0.9300 ?
    C6B H6B . 0.9300 ?
    C11B C12B . 1.306(3) ?
    C11B H11B . 0.9300 ?
    C12B C13B . 1.463(4) ?
    C12B H12B . 0.9300 ?
    C13B O12B . 1.256(3) ?
    C13B O11B . 1.267(3) ?
    C21B O21B . 1.427(2) ?
    C21B C22B . 1.498(3) ?
    C21B H21A . 0.9700 ?
    C21B H21B . 0.9700 ?
    C22B H22D . 0.9600 ?
    C22B H22E . 0.9600 ?
    C22B H22F . 0.9600 ?
    O12B H1B . 1.3137 ?
    C1C C2C . 1.392(3) ?
    C1C C6C . 1.394(3) ?
    C1C C11C . 1.449(3) ?
    C2C O21C . 1.370(3) ?
    C2C C3C . 1.372(3) ?
    C3C C4C . 1.375(4) ?
    C3C H3C . 0.9300 ?
    C4C C5C . 1.366(4) ?
    C4C H4C . 0.9300 ?
    C5C C6C . 1.362(4) ?
    C5C H5C . 0.9300 ?
    C6C H6C . 0.9300 ?
    C11C C12C . 1.317(3) ?
    C11C H11C . 0.9300 ?
    C12C C13C . 1.461(4) ?
    C12C H12C . 0.9300 ?
    C13C O12C . 1.261(3) ?
    C13C O11C . 1.262(3) ?
    C21C O21C . 1.430(3) ?
    C21C C22C . 1.476(3) ?
    C21C H21C . 0.9700 ?
    C21C H21D . 0.9700 ?
    C22C H22A . 0.9600 ?
    C22C H22B . 0.9600 ?
    C22C H22C . 0.9600 ?
    O12C H1C . 1.2714 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C2A C1A C6A . . 117.3(3) ?
    C2A C1A C11A . . 119.7(3) ?
    C6A C1A C11A . . 123.0(3) ?
    O21A C2A C3A . . 123.7(3) ?
    O21A C2A C1A . . 115.3(3) ?
    C3A C2A C1A . . 121.0(3) ?
    C2A C3A C4A . . 119.8(3) ?
    C2A C3A H3A . . 120.1 ?
    C4A C3A H3A . . 120.1 ?
    C5A C4A C3A . . 121.0(4) ?
    C5A C4A H4A . . 119.5 ?
    C3A C4A H4A . . 119.5 ?
    C4A C5A C6A . . 119.0(3) ?
    C4A C5A H5A . . 120.5 ?
    C6A C5A H5A . . 120.5 ?
    C5A C6A C1A . . 121.9(3) ?
    C5A C6A H6A . . 119.0 ?
    C1A C6A H6A . . 119.0 ?
    C12A C11A C1A . . 127.3(3) ?
    C12A C11A H11A . . 116.4 ?
    C1A C11A H11A . . 116.4 ?
    C11A C12A C13A . . 123.5(3) ?
    C11A C12A H12A . . 118.3 ?
    C13A C12A H12A . . 118.3 ?
    O11A C13A O12A . . 123.6(3) ?
    O11A C13A C12A . . 117.2(3) ?
    O12A C13A C12A . . 119.2(3) ?
    O21A C21A C22A . . 108.0(3) ?
    O21A C21A H21E . . 110.1 ?
    C22A C21A H21E . . 110.1 ?
    O21A C21A H21F . . 110.1 ?
    C22A C21A H21F . . 110.1 ?
    H21E C21A H21F . . 108.4 ?
    C21A C22A H22G . . 109.5 ?
    C21A C22A H22H . . 109.5 ?
    H22G C22A H22H . . 109.5 ?
    C21A C22A H22I . . 109.5 ?
    H22G C22A H22I . . 109.5 ?
    H22H C22A H22I . . 109.5 ?
    C13A O12A H1A . . 121.5 ?
    C2A O21A C21A . . 119.2(2) ?
    C2B C1B C6B . . 116.8(3) ?
    C2B C1B C11B . . 120.9(3) ?
    C6B C1B C11B . . 122.3(3) ?
    C3B C2B O21B . . 123.2(3) ?
    C3B C2B C1B . . 121.3(3) ?
    O21B C2B C1B . . 115.4(3) ?
    C2B C3B C4B . . 119.6(3) ?
    C2B C3B H3B . . 120.2 ?
    C4B C3B H3B . . 120.2 ?
    C5B C4B C3B . . 120.9(3) ?
    C5B C4B H4B . . 119.6 ?
    C3B C4B H4B . . 119.6 ?
    C6B C5B C4B . . 119.2(3) ?
    C6B C5B H5B . . 120.4 ?
    C4B C5B H5B . . 120.4 ?
    C5B C6B C1B . . 122.2(3) ?
    C5B C6B H6B . . 118.9 ?
    C1B C6B H6B . . 118.9 ?
    C12B C11B C1B . . 128.5(3) ?
    C12B C11B H11B . . 115.8 ?
    C1B C11B H11B . . 115.8 ?
    C11B C12B C13B . . 124.5(3) ?
    C11B C12B H12B . . 117.7 ?
    C13B C12B H12B . . 117.7 ?
    O12B C13B O11B . . 123.7(3) ?
    O12B C13B C12B . . 119.3(3) ?
    O11B C13B C12B . . 117.0(3) ?
    O21B C21B C22B . . 107.3(2) ?
    O21B C21B H21A . . 110.2 ?
    C22B C21B H21A . . 110.2 ?
    O21B C21B H21B . . 110.2 ?
    C22B C21B H21B . . 110.2 ?
    H21A C21B H21B . . 108.5 ?
    C21B C22B H22D . . 109.5 ?
    C21B C22B H22E . . 109.5 ?
    H22D C22B H22E . . 109.5 ?
    C21B C22B H22F . . 109.5 ?
    H22D C22B H22F . . 109.5 ?
    H22E C22B H22F . . 109.5 ?
    C13B O12B H1B . . 119.2 ?
    C2B O21B C21B . . 118.8(2) ?
    C2C C1C C6C . . 116.9(3) ?
    C2C C1C C11C . . 120.2(3) ?
    C6C C1C C11C . . 122.9(3) ?
    O21C C2C C3C . . 123.6(3) ?
    O21C C2C C1C . . 115.0(3) ?
    C3C C2C C1C . . 121.4(3) ?
    C2C C3C C4C . . 119.7(3) ?
    C2C C3C H3C . . 120.2 ?
    C4C C3C H3C . . 120.2 ?
    C5C C4C C3C . . 120.4(3) ?
    C5C C4C H4C . . 119.8 ?
    C3C C4C H4C . . 119.8 ?
    C6C C5C C4C . . 119.6(3) ?
    C6C C5C H5C . . 120.2 ?
    C4C C5C H5C . . 120.2 ?
    C5C C6C C1C . . 122.0(3) ?
    C5C C6C H6C . . 119.0 ?
    C1C C6C H6C . . 119.0 ?
    C12C C11C C1C . . 128.0(3) ?
    C12C C11C H11C . . 116.0 ?
    C1C C11C H11C . . 116.0 ?
    C11C C12C C13C . . 123.7(3) ?
    C11C C12C H12C . . 118.1 ?
    C13C C12C H12C . . 118.1 ?
    O12C C13C O11C . . 122.5(3) ?
    O12C C13C C12C . . 119.6(3) ?
    O11C C13C C12C . . 117.9(3) ?
    O21C C21C C22C . . 107.5(2) ?
    O21C C21C H21C . . 110.2 ?
    C22C C21C H21C . . 110.2 ?
    O21C C21C H21D . . 110.2 ?
    C22C C21C H21D . . 110.2 ?
    H21C C21C H21D . . 108.5 ?
    C21C C22C H22A . . 109.5 ?
    C21C C22C H22B . . 109.5 ?
    H22A C22C H22B . . 109.5 ?
    C21C C22C H22C . . 109.5 ?
    H22A C22C H22C . . 109.5 ?
    H22B C22C H22C . . 109.5 ?
    C13C O12C H1C . . 118.1 ?
    C2C O21C C21C . . 118.8(2) ?
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C6A C1A C2A O21A . . . . 179.9(2) ?
    C11A C1A C2A O21A . . . . 0.4(4) ?
    C6A C1A C2A C3A . . . . 0.1(4) ?
    C11A C1A C2A C3A . . . . -179.4(3) ?
    O21A C2A C3A C4A . . . . -179.7(3) ?
    C1A C2A C3A C4A . . . . 0.0(5) ?
    C2A C3A C4A C5A . . . . 0.0(5) ?
    C3A C4A C5A C6A . . . . -0.3(6) ?
    C4A C5A C6A C1A . . . . 0.4(5) ?
    C2A C1A C6A C5A . . . . -0.4(5) ?
    C11A C1A C6A C5A . . . . 179.2(3) ?
    C2A C1A C11A C12A . . . . -177.0(3) ?
    C6A C1A C11A C12A . . . . 3.4(5) ?
    C1A C11A C12A C13A . . . . 178.5(3) ?
    C11A C12A C13A O11A . . . . -180.0(3) ?
    C11A C12A C13A O12A . . . . 0.0(5) ?
    C3A C2A O21A C21A . . . . 1.3(4) ?
    C1A C2A O21A C21A . . . . -178.5(2) ?
    C22A C21A O21A C2A . . . . 177.4(3) ?
    C6B C1B C2B C3B . . . . 0.2(4) ?
    C11B C1B C2B C3B . . . . 179.9(3) ?
    C6B C1B C2B O21B . . . . 180.0(2) ?
    C11B C1B C2B O21B . . . . -0.4(4) ?
    O21B C2B C3B C4B . . . . 179.8(3) ?
    C1B C2B C3B C4B . . . . -0.5(4) ?
    C2B C3B C4B C5B . . . . 0.4(5) ?
    C3B C4B C5B C6B . . . . -0.1(6) ?
    C4B C5B C6B C1B . . . . -0.2(5) ?
    C2B C1B C6B C5B . . . . 0.1(4) ?
    C11B C1B C6B C5B . . . . -179.6(3) ?
    C2B C1B C11B C12B . . . . -171.7(3) ?
    C6B C1B C11B C12B . . . . 7.9(5) ?
    C1B C11B C12B C13B . . . . -179.7(3) ?
    C11B C12B C13B O12B . . . . 6.2(4) ?
    C11B C12B C13B O11B . . . . -172.9(3) ?
    C3B C2B O21B C21B . . . . -1.3(4) ?
    C1B C2B O21B C21B . . . . 179.0(2) ?
    C22B C21B O21B C2B . . . . -177.7(2) ?
    C6C C1C C2C O21C . . . . -179.6(2) ?
    C11C C1C C2C O21C . . . . -1.3(4) ?
    C6C C1C C2C C3C . . . . 0.3(4) ?
    C11C C1C C2C C3C . . . . 178.7(2) ?
    O21C C2C C3C C4C . . . . 179.7(3) ?
    C1C C2C C3C C4C . . . . -0.3(5) ?
    C2C C3C C4C C5C . . . . -0.1(5) ?
    C3C C4C C5C C6C . . . . 0.4(5) ?
    C4C C5C C6C C1C . . . . -0.3(5) ?
    C2C C1C C6C C5C . . . . 0.0(4) ?
    C11C C1C C6C C5C . . . . -178.3(3) ?
    C2C C1C C11C C12C . . . . -177.6(3) ?
    C6C C1C C11C C12C . . . . 0.7(4) ?
    C1C C11C C12C C13C . . . . 179.9(3) ?
    C11C C12C C13C O12C . . . . 3.3(5) ?
    C11C C12C C13C O11C . . . . -177.6(3) ?
    C3C C2C O21C C21C . . . . -7.6(4) ?
    C1C C2C O21C C21C . . . . 172.4(2) ?
    C22C C21C O21C C2C . . . . -171.0(2) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    O12C H1C O11B 2_766 1.27 1.38 2.640(3) 170.9
    O12B H1B O11C 2_766 1.31 1.34 2.646(3) 169.5
    O12A H1A O11A 2_655 1.26 1.38 2.630(3) 170.1
data_d6h_s
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2003-11-12
_journal_date_accepted     2004-04-15
_journal_name_full     'Acta Crystallographica, Section B'
_journal_year     2004
_journal_volume     60
_journal_issue      3
_journal_page_first     300
_journal_page_last     314
_journal_paper_category     FA
_chemical_name_systematic
;
  (E)-3-(2-Ethoxyphenyl)propenoic acid and
trans-2,4-bis(2-ethoxyphenyl)-trans-1,3-cyclobutane-dicarboxylic acid
;
_chemical_name_common
;
ortho-ethoxy-trans-cinnamic acid and 2,2'-diethoxy alpha-truxillic acid
;
_chemical_formula_moiety     '2.738(C11 H12 O3), 0.131(C22 H24 O6)'
_chemical_formula_sum     'C33 H36 O9'
_chemical_formula_weight     576.62
_chemical_melting_point     ?
_symmetry_cell_setting     Triclinic
_symmetry_space_group_name_H-M     P-1
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     8.6759(11)
_cell_length_b     11.0003(13)
_cell_length_c     17.299(2)
_cell_angle_alpha     92.552(3)
_cell_angle_beta     92.347(2)
_cell_angle_gamma     111.155(3)
_cell_volume     1535.3(3)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     781
_cell_measurement_theta_min     2.25
_cell_measurement_theta_max     21.40
_cell_measurement_temperature     293(2)
_exptl_crystal_description     irregular
_exptl_crystal_colour     white
_exptl_crystal_size_max     0.38
_exptl_crystal_size_mid     0.33
_exptl_crystal_size_min     0.26
_exptl_crystal_density_diffrn     1.247
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     612
_exptl_absorpt_coefficient_mu     0.090
_exptl_absorpt_correction_type     None
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_exptl_special_details
;
The following alerts are triggered when using the ACTA-C CIF validation
software.
PLAT301_ALERT_3_B Main Residue  Disorder ......................... 40.00 Perc.
PLAT432_ALERT_2_B Short Inter X...Y Contact  C3C    ..  C4D     ..  3.05 Ang.
PLAT432_ALERT_2_B Short Inter X...Y Contact  C4C    ..  C3D     ..  3.07 Ang.
PLAT165_ALERT_3_C Nr. of Status R Flagged Non-Hydrogen Atoms .....      28
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...       6
PLAT432_ALERT_2_C Short Inter X...Y Contact  C3C    ..  C3D     ..  3.13 Ang.
------
Authors comment: The assymetric unit consists of a mixture of the monomer
and dimer. The short contacts are most probably due to the dimer not being
properly optimised for the crystal structure at this point. Coordinates
for the dimer molecule at a higher conversion stage was used as a starting
point for the refinement. The dimer was also refined isotropically
as a rigid body. This is necessary as the dimer is only present in about 4-5%
occupancy (4% dimer occupancy = 8% of monomer consumed).
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....    41 Perc.
-------
Authors comment: The crystal was exposed to 6 hours to UV light allowing
some reaction to occur. This has most probably caused a certain amount of
disorder leading to higher angle reflections having lower intensity
than expected.The number of observed reflections has most probably decreased
as a consequence.
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....      ?
------
Authors commment: Our moiety formula is correct as it takes the occupancy
of the dimer and monomer molecules into account.
;
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART 1K'
_diffrn_measurement_method     'phi and omega scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     8251
_diffrn_reflns_av_R_equivalents     0.0280
_diffrn_reflns_av_sigmaI/netI     0.0642
_diffrn_reflns_theta_min     1.18
_diffrn_reflns_theta_max     25.00
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.995
_diffrn_measured_fraction_theta_full     0.995
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -11
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     -20
_diffrn_reflns_limit_l_max     14
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     5391
_reflns_number_gt     2192
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1600
_refine_ls_R_factor_gt     0.0678
_refine_ls_wR_factor_gt     0.1724
_refine_ls_wR_factor_ref     0.2202
_refine_ls_goodness_of_fit_ref     0.904
_refine_ls_restrained_S_all     0.904
_refine_ls_number_reflns     5391
_refine_ls_number_parameters     391
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.1128P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.194
_refine_diff_density_min     -0.182
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef     0.008(2)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 0.0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0106 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'SMART-NT (Bruker, 1998)'
_computing_cell_refinement     'SAINT+(Bruker, 1999a)'
_computing_data_reduction     'SAINT+(Bruker, 1999a)'
_computing_structure_solution     'SHELXTL (Bruker, 1999b)'
_computing_structure_refinement     'SHELXTL (Bruker, 1999b)'
_computing_molecular_graphics
;
PLATON (Spek, 2003), SHELXTL (Bruker, 1999b),
SCHAKAL-97 (Keller, 1997) and DS ViewerPro (Accelrys, 2002)
;
_computing_publication_material     'SHELXTL (Bruker, 1999b)'
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
    C1A 1.0151(6) 0.0304(4) 0.2213(2) 0.0733(12) Uani d P 0.869(3) A 2 C
    C2A 1.0109(6) 0.0251(4) 0.3015(2) 0.0761(12) Uani d P 0.869(3) A 2 C
    C3A 1.1502(6) 0.0346(4) 0.3466(3) 0.0924(14) Uani d P 0.869(3) A 2 C
    H3A 1.1462 0.0325 0.4002 0.111 Uiso calc PR 0.869(3) A 2 H
    C4A 1.2944(6) 0.0472(5) 0.3126(4) 0.1040(16) Uani d P 0.869(3) A 2 C
    H4A 1.3873 0.0515 0.3430 0.125 Uiso calc PR 0.869(3) A 2 H
    C5A 1.3022(7) 0.0535(5) 0.2333(4) 0.1062(17) Uani d P 0.869(3) A 2 C
    H5A 1.4009 0.0647 0.2102 0.127 Uiso calc PR 0.869(3) A 2 H
    C6A 1.1624(8) 0.0431(5) 0.1888(3) 0.0976(15) Uani d P 0.869(3) A 2 C
    H6A 1.1673 0.0446 0.1353 0.117 Uiso calc PR 0.869(3) A 2 H
    C11A 0.8643(5) 0.0194(3) 0.1735(2) 0.0738(12) Uani d P 0.869(3) A 2 C
    H11A 0.7708 0.0117 0.2003 0.089 Uiso calc PR 0.869(3) A 2 H
    C12A 0.8480(6) 0.0194(4) 0.0976(2) 0.0814(13) Uani d P 0.869(3) A 2 C
    H12A 0.9397 0.0272 0.0693 0.098 Uiso calc PR 0.869(3) A 2 H
    C13A 0.6944(6) 0.0077(4) 0.0553(3) 0.0809(13) Uani d P 0.869(3) A 2 C
    C21A 0.8468(7) 0.0093(5) 0.4133(2) 0.0951(14) Uani d P 0.869(3) A 2 C
    H21C 0.9285 0.0874 0.4391 0.114 Uiso calc PR 0.869(3) A 2 H
    H21D 0.8647 -0.0663 0.4326 0.114 Uiso calc PR 0.869(3) A 2 H
    C22A 0.6766(7) 0.0035(6) 0.4279(3) 0.1086(16) Uani d P 0.869(3) A 2 C
    H22D 0.6604 0.0785 0.4083 0.163 Uiso calc PR 0.869(3) A 2 H
    H22E 0.6624 0.0026 0.4827 0.163 Uiso calc PR 0.869(3) A 2 H
    H22F 0.5972 -0.0745 0.4022 0.163 Uiso calc PR 0.869(3) A 2 H
    O11A 0.6914(4) 0.0087(3) -0.01701(17) 0.0957(10) Uani d P 0.869(3) A 2 O
    O12A 0.5711(5) -0.0035(3) 0.09473(19) 0.1040(11) Uani d P 0.869(3) A 2 O
    H1A 0.4916 -0.0085 0.0657 0.156 Uiso calc PR 0.869(3) A 2 H
    O21A 0.8606(5) 0.0111(4) 0.33080(16) 0.0899(9) Uani d P 0.869(3) A 2 O
    C1B 0.7939(5) 0.3471(4) 0.1306(2) 0.0661(10) Uani d P 0.869(3) A 2 C
    C2B 0.7929(5) 0.3366(4) 0.0494(2) 0.0657(10) Uani d P 0.869(3) A 2 C
    C3B 0.6538(6) 0.3308(4) 0.0043(3) 0.0848(14) Uani d P 0.869(3) A 2 C
    H3B 0.6531 0.3218 -0.0495 0.102 Uiso calc PR 0.869(3) A 2 H
    C4B 0.5175(6) 0.3384(5) 0.0389(3) 0.1009(16) Uani d P 0.869(3) A 2 C
    H4B 0.4255 0.3358 0.0084 0.121 Uiso calc PR 0.869(3) A 2 H
    C5B 0.5164(7) 0.3497(6) 0.1182(4) 0.1037(16) Uani d P 0.869(3) A 2 C
    H5B 0.4234 0.3536 0.1414 0.124 Uiso calc PR 0.869(3) A 2 H
    C6B 0.6547(6) 0.3553(4) 0.1632(3) 0.0861(13) Uani d P 0.869(3) A 2 C
    H6B 0.6540 0.3648 0.2169 0.103 Uiso calc PR 0.869(3) A 2 H
    C11B 0.9396(5) 0.3533(3) 0.1780(2) 0.0636(10) Uani d P 0.869(3) A 2 C
    H11B 1.0333 0.3595 0.1518 0.076 Uiso calc PR 0.869(3) A 2 H
    C12B 0.9532(5) 0.3510(4) 0.2543(2) 0.0736(12) Uani d P 0.869(3) A 2 C
    H12B 0.8616 0.3445 0.2822 0.088 Uiso calc PR 0.869(3) A 2 H
    C13B 1.1052(6) 0.3584(4) 0.2963(2) 0.0724(12) Uani d P 0.869(3) A 2 C
    C21B 0.9379(6) 0.3138(4) -0.0625(2) 0.0761(12) Uani d P 0.869(3) A 2 C
    H21E 0.9277 0.3886 -0.0867 0.091 Uiso calc PR 0.869(3) A 2 H
    H21F 0.8477 0.2359 -0.0832 0.091 Uiso calc PR 0.869(3) A 2 H
    C22B 1.1002(6) 0.3028(5) -0.0782(2) 0.0921(14) Uani d P 0.869(3) A 2 C
    H22G 1.1884 0.3815 -0.0589 0.138 Uiso calc PR 0.869(3) A 2 H
    H22H 1.1067 0.2900 -0.1331 0.138 Uiso calc PR 0.869(3) A 2 H
    H22I 1.1100 0.2299 -0.0528 0.138 Uiso calc PR 0.869(3) A 2 H
    O11B 1.0958(4) 0.3432(3) 0.36910(15) 0.0883(10) Uani d P 0.869(3) A 2 O
    H1B 1.1862 0.3480 0.3881 0.132 Uiso calc PR 0.869(3) A 2 H
    O12B 1.2360(4) 0.3790(3) 0.26206(17) 0.0877(9) Uani d P 0.869(3) A 2 O
    O21B 0.9329(4) 0.3290(3) 0.01970(14) 0.0751(8) Uani d P 0.869(3) A 2 O
    C1C 0.2163(4) 0.6710(3) 0.42390(19) 0.0688(9) Uani d . 1 . . C
    C2C 0.2291(4) 0.6868(3) 0.34529(19) 0.0743(10) Uani d . 1 . . C
    C3C 0.0957(5) 0.6907(4) 0.2992(2) 0.0975(12) Uani d . 1 . . C
    H3C 0.1049 0.7015 0.2464 0.117 Uiso calc R 1 . . H
    C4C -0.0505(5) 0.6785(4) 0.3330(3) 0.1070(13) Uani d . 1 . . C
    H4C -0.1406 0.6800 0.3026 0.128 Uiso calc R 1 . . H
    C5C -0.0636(6) 0.6640(4) 0.4113(3) 0.1041(13) Uani d . 1 . . C
    H5C -0.1617 0.6570 0.4338 0.125 Uiso calc R 1 . . H
    C6C 0.0680(5) 0.6598(3) 0.4562(2) 0.0882(11) Uani d . 1 . . C
    H6C 0.0580 0.6494 0.5091 0.106 Uiso calc R 1 . . H
    C11C 0.3570(4) 0.6642(3) 0.47092(19) 0.0700(9) Uani d . 1 . . C
    H11C 0.4524 0.6741 0.4451 0.084 Uiso calc R 1 . . H
    C12C 0.3643(5) 0.6455(3) 0.54595(19) 0.0805(10) Uani d . 1 . . C
    H12C 0.2720 0.6366 0.5739 0.097 Uiso calc R 1 . . H
    C13C 0.5116(5) 0.6382(3) 0.58652(19) 0.0796(11) Uani d . 1 . . C
    C21C 0.3944(4) 0.7049(4) 0.23477(18) 0.0846(11) Uani d . 1 . . C
    H21A 0.3861 0.7855 0.2180 0.102 Uiso calc R 1 . . H
    H21B 0.3080 0.6320 0.2068 0.102 Uiso calc R 1 . . H
    C22C 0.5601(4) 0.7008(4) 0.2197(2) 0.0953(12) Uani d . 1 . . C
    H22A 0.6443 0.7729 0.2481 0.143 Uiso calc R 1 . . H
    H22B 0.5769 0.7067 0.1653 0.143 Uiso calc R 1 . . H
    H22C 0.5662 0.6203 0.2360 0.143 Uiso calc R 1 . . H
    O11C 0.4971(3) 0.6124(3) 0.65788(13) 0.1059(9) Uani d . 1 . . O
    H1C 0.5846 0.6101 0.6763 0.159 Uiso calc R 1 . . H
    O12C 0.6431(3) 0.6588(2) 0.55318(13) 0.0957(8) Uani d . 1 . . O
    O21C 0.3774(3) 0.6973(2) 0.31633(12) 0.0854(7) Uani d . 1 . . O
    C1D 1.0193(15) 0.0446(10) 0.2376(7) 0.078(3) Uiso d PG 0.131(3) A 1 C
    C2D 1.0034(18) 0.0066(12) 0.3131(7) 0.078(3) Uiso d PG 0.131(3) A 1 C
    C3D 1.129(2) -0.0246(15) 0.3525(9) 0.078(3) Uiso d PG 0.131(3) A 1 C
    H3D 1.1161 -0.0523 0.4026 0.094 Uiso calc PR 0.131(3) A 1 H
    C4D 1.271(2) -0.0131(18) 0.3149(10) 0.078(3) Uiso d PG 0.131(3) A 1 C
    H4D 1.3555 -0.0315 0.3409 0.094 Uiso calc PR 0.131(3) A 1 H
    C5D 1.2909(19) 0.0247(18) 0.2406(10) 0.078(3) Uiso d PG 0.131(3) A 1 C
    H5D 1.3862 0.0306 0.2158 0.094 Uiso calc PR 0.131(3) A 1 H
    C6D 1.1654(16) 0.0541(14) 0.2029(8) 0.078(3) Uiso d PG 0.131(3) A 1 C
    H6D 1.1792 0.0811 0.1526 0.094 Uiso calc PR 0.131(3) A 1 H
    C11D 0.8894(12) 0.0911(8) 0.2048(6) 0.078(3) Uiso d PG 0.131(3) A 1 C
    H11D 0.7790 0.0294 0.2146 0.094 Uiso calc PR 0.131(3) A 1 H
    C12D 0.8940(12) 0.1274(9) 0.1198(5) 0.078(3) Uiso d PG 0.131(3) A 1 C
    H12D 0.9920 0.1235 0.0952 0.094 Uiso calc PR 0.131(3) A 1 H
    C13D 0.7332(14) 0.0555(10) 0.0702(6) 0.078(3) Uiso d PG 0.131(3) A 1 C
    C21D 0.845(2) -0.0164(18) 0.4253(7) 0.078(3) Uiso d PG 0.131(3) A 1 C
    H21G 0.9355 0.0516 0.4542 0.094 Uiso calc PR 0.131(3) A 1 H
    H21H 0.8485 -0.1004 0.4376 0.094 Uiso calc PR 0.131(3) A 1 H
    C22D 0.681(2) -0.008(2) 0.4465(8) 0.078(3) Uiso d PG 0.131(3) A 1 C
    H22J 0.6687 -0.0181 0.5010 0.117 Uiso calc PR 0.131(3) A 1 H
    H22K 0.5919 -0.0756 0.4177 0.117 Uiso calc PR 0.131(3) A 1 H
    H22L 0.6785 0.0758 0.4342 0.117 Uiso calc PR 0.131(3) A 1 H
    O11D 0.7562(18) 0.0505(13) -0.0048(6) 0.078(3) Uiso d PG 0.131(3) A 1 O
    H1D 0.6673 0.0113 -0.0288 0.117 Uiso calc PR 0.131(3) A 1 H
    O12D 0.5962(13) 0.0209(12) 0.0952(8) 0.078(3) Uiso d PG 0.131(3) A 1 O
    O21D 0.8578(19) -0.0007(14) 0.3443(7) 0.078(3) Uiso d PG 0.131(3) A 1 O
    C1E 0.7855(16) 0.3239(11) 0.1128(7) 0.078(3) Uiso d PG 0.131(3) A 1 C
    C2E 0.7950(19) 0.3461(12) 0.0348(7) 0.078(3) Uiso d PG 0.131(3) A 1 C
    C3E 0.669(2) 0.3721(16) -0.0060(9) 0.078(3) Uiso d PG 0.131(3) A 1 C
    H3E 0.6754 0.3869 -0.0584 0.094 Uiso calc PR 0.131(3) A 1 H
    C4E 0.533(2) 0.3754(19) 0.0333(11) 0.078(3) Uiso d PG 0.131(3) A 1 C
    H4E 0.4490 0.3926 0.0066 0.094 Uiso calc PR 0.131(3) A 1 H
    C5E 0.522(2) 0.3539(19) 0.1104(11) 0.078(3) Uiso d PG 0.131(3) A 1 C
    H5E 0.4311 0.3571 0.1362 0.094 Uiso calc PR 0.131(3) A 1 H
    C6E 0.6475(18) 0.3274(15) 0.1497(9) 0.078(3) Uiso d PG 0.131(3) A 1 C
    H6E 0.6393 0.3115 0.2021 0.094 Uiso calc PR 0.131(3) A 1 H
    C11E 0.9129(12) 0.2741(8) 0.1470(6) 0.078(3) Uiso d PG 0.131(3) A 1 C
    H11E 1.0244 0.3344 0.1378 0.094 Uiso calc PR 0.131(3) A 1 H
    C12E 0.9060(12) 0.2380(9) 0.2321(6) 0.078(3) Uiso d PG 0.131(3) A 1 C
    H12E 0.8065 0.2408 0.2558 0.094 Uiso calc PR 0.131(3) A 1 H
    C13E 1.0633(15) 0.3090(10) 0.2832(6) 0.078(3) Uiso d PG 0.131(3) A 1 C
    C21E 0.937(2) 0.3347(18) -0.0810(7) 0.078(3) Uiso d PG 0.131(3) A 1 C
    H21I 0.9376 0.4155 -0.1013 0.094 Uiso calc PR 0.131(3) A 1 H
    H21J 0.8398 0.2637 -0.1028 0.094 Uiso calc PR 0.131(3) A 1 H
    C22E 1.093(2) 0.311(2) -0.1017(7) 0.078(3) Uiso d PG 0.131(3) A 1 C
    H22M 1.0974 0.3046 -0.1571 0.117 Uiso calc PR 0.131(3) A 1 H
    H22N 1.0915 0.2303 -0.0813 0.117 Uiso calc PR 0.131(3) A 1 H
    H22O 1.1889 0.3814 -0.0799 0.117 Uiso calc PR 0.131(3) A 1 H
    O11E 1.0390(19) 0.2985(13) 0.3569(6) 0.078(3) Uiso d PG 0.131(3) A 1 O
    H1E 1.1262 0.3378 0.3823 0.117 Uiso calc PR 0.131(3) A 1 H
    O12E 1.2002(14) 0.3558(11) 0.2574(8) 0.078(3) Uiso d PG 0.131(3) A 1 O
    O21E 0.9371(19) 0.3427(13) 0.0023(7) 0.078(3) Uiso d PG 0.131(3) A 1 O
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
    C1A C6A . 1.380(5) ?
    C1A C2A . 1.394(5) ?
    C1A C11A . 1.482(6) ?
    C2A O21A . 1.377(4) ?
    C2A C3A . 1.380(6) ?
    C3A C4A . 1.368(6) ?
    C3A H3A . 0.9300 ?
    C4A C5A . 1.380(6) ?
    C4A H4A . 0.9300 ?
    C5A C6A . 1.375(6) ?
    C5A H5A . 0.9300 ?
    C6A H6A . 0.9300 ?
    C11A C12A . 1.316(5) ?
    C11A H11A . 0.9300 ?
    C12A C13A . 1.454(6) ?
    C12A H12A . 0.9300 ?
    C13A O11A . 1.251(4) ?
    C13A O12A . 1.264(5) ?
    C21A O21A . 1.437(4) ?
    C21A C22A . 1.488(6) ?
    C21A H21C . 0.9700 ?
    C21A H21D . 0.9700 ?
    C22A H22D . 0.9600 ?
    C22A H22E . 0.9600 ?
    C22A H22F . 0.9600 ?
    O12A H1A . 0.8200 ?
    C1B C6B . 1.384(5) ?
    C1B C2B . 1.403(5) ?
    C1B C11B . 1.458(5) ?
    C2B O21B . 1.367(4) ?
    C2B C3B . 1.390(5) ?
    C3B C4B . 1.374(5) ?
    C3B H3B . 0.9300 ?
    C4B C5B . 1.373(6) ?
    C4B H4B . 0.9300 ?
    C5B C6B . 1.385(6) ?
    C5B H5B . 0.9300 ?
    C6B H6B . 0.9300 ?
    C11B C12B . 1.321(5) ?
    C11B H11B . 0.9300 ?
    C12B C13B . 1.454(5) ?
    C12B H12B . 0.9300 ?
    C13B O12B . 1.254(4) ?
    C13B O11B . 1.279(4) ?
    C21B O21B . 1.429(4) ?
    C21B C22B . 1.491(5) ?
    C21B H21E . 0.9700 ?
    C21B H21F . 0.9700 ?
    C22B H22G . 0.9600 ?
    C22B H22H . 0.9600 ?
    C22B H22I . 0.9600 ?
    O11B H1B . 0.8200 ?
    C1C C2C . 1.382(4) ?
    C1C C6C . 1.391(4) ?
    C1C C11C . 1.466(4) ?
    C2C O21C . 1.368(4) ?
    C2C C3C . 1.393(5) ?
    C3C C4C . 1.383(5) ?
    C3C H3C . 0.9300 ?
    C4C C5C . 1.376(5) ?
    C4C H4C . 0.9300 ?
    C5C C6C . 1.369(5) ?
    C5C H5C . 0.9300 ?
    C6C H6C . 0.9300 ?
    C11C C12C . 1.326(4) ?
    C11C H11C . 0.9300 ?
    C12C C13C . 1.462(5) ?
    C12C H12C . 0.9300 ?
    C13C O12C . 1.251(4) ?
    C13C O11C . 1.280(4) ?
    C21C O21C . 1.428(3) ?
    C21C C22C . 1.488(4) ?
    C21C H21A . 0.9700 ?
    C21C H21B . 0.9700 ?
    C22C H22A . 0.9600 ?
    C22C H22B . 0.9600 ?
    C22C H22C . 0.9600 ?
    O11C H1C . 0.8200 ?
    C1D C2D . 1.3865 ?
    C1D C6D . 1.3961 ?
    C1D C11D . 1.4979 ?
    C2D O21D . 1.3716 ?
    C2D C3D . 1.4116 ?
    C3D C4D . 1.3885 ?
    C3D H3D . 0.9300 ?
    C4D C5D . 1.3674 ?
    C4D H4D . 0.9300 ?
    C5D C6D . 1.3890 ?
    C5D H5D . 0.9300 ?
    C6D H6D . 0.9300 ?
    C11D C12D . 1.5394 ?
    C11D C12E . 1.6166 ?
    C11D H11D . 0.9800 ?
    C12D C13D . 1.5337 ?
    C12D C11E . 1.6084 ?
    C12D H12D . 0.9800 ?
    C13D O12D . 1.2148 ?
    C13D O11D . 1.3234 ?
    C21D O21D . 1.4229 ?
    C21D C22D . 1.5151 ?
    C21D H21G . 0.9700 ?
    C21D H21H . 0.9700 ?
    C22D H22J . 0.9600 ?
    C22D H22K . 0.9600 ?
    C22D H22L . 0.9600 ?
    O11D H1D . 0.8200 ?
    C1E C2E . 1.3829 ?
    C1E C6E . 1.3919 ?
    C1E C11E . 1.5118 ?
    C2E O21E . 1.3878 ?
    C2E C3E . 1.3985 ?
    C3E C4E . 1.3933 ?
    C3E H3E . 0.9300 ?
    C4E C5E . 1.3663 ?
    C4E H4E . 0.9300 ?
    C5E C6E . 1.3865 ?
    C5E H5E . 0.9300 ?
    C6E H6E . 0.9300 ?
    C11E C12E . 1.5393 ?
    C11E H11E . 0.9800 ?
    C12E C13E . 1.5245 ?
    C12E H12E . 0.9800 ?
    C13E O12E . 1.2245 ?
    C13E O11E . 1.3047 ?
    C21E O21E . 1.4391 ?
    C21E C22E . 1.5213 ?
    C21E H21I . 0.9700 ?
    C21E H21J . 0.9700 ?
    C22E H22M . 0.9600 ?
    C22E H22N . 0.9600 ?
    C22E H22O . 0.9600 ?
    O11E H1E . 0.8200 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C6A C1A C2A . . 117.5(5) ?
    C6A C1A C11A . . 122.2(4) ?
    C2A C1A C11A . . 120.3(4) ?
    O21A C2A C3A . . 124.0(4) ?
    O21A C2A C1A . . 115.2(4) ?
    C3A C2A C1A . . 120.9(4) ?
    C4A C3A C2A . . 120.1(4) ?
    C4A C3A H3A . . 120.0 ?
    C2A C3A H3A . . 120.0 ?
    C3A C4A C5A . . 120.2(5) ?
    C3A C4A H4A . . 119.9 ?
    C5A C4A H4A . . 119.9 ?
    C6A C5A C4A . . 119.2(5) ?
    C6A C5A H5A . . 120.4 ?
    C4A C5A H5A . . 120.4 ?
    C5A C6A C1A . . 122.0(5) ?
    C5A C6A H6A . . 119.0 ?
    C1A C6A H6A . . 119.0 ?
    C12A C11A C1A . . 127.3(4) ?
    C12A C11A H11A . . 116.3 ?
    C1A C11A H11A . . 116.3 ?
    C11A C12A C13A . . 123.6(4) ?
    C11A C12A H12A . . 118.2 ?
    C13A C12A H12A . . 118.2 ?
    O11A C13A O12A . . 124.0(5) ?
    O11A C13A C12A . . 118.8(4) ?
    O12A C13A C12A . . 117.2(4) ?
    O21A C21A C22A . . 106.8(4) ?
    O21A C21A H21C . . 110.4 ?
    C22A C21A H21C . . 110.4 ?
    O21A C21A H21D . . 110.4 ?
    C22A C21A H21D . . 110.4 ?
    H21C C21A H21D . . 108.6 ?
    C21A C22A H22D . . 109.5 ?
    C21A C22A H22E . . 109.5 ?
    H22D C22A H22E . . 109.5 ?
    C21A C22A H22F . . 109.5 ?
    H22D C22A H22F . . 109.5 ?
    H22E C22A H22F . . 109.5 ?
    C13A O12A H1A . . 109.5 ?
    C2A O21A C21A . . 118.8(3) ?
    C6B C1B C2B . . 117.7(4) ?
    C6B C1B C11B . . 121.8(4) ?
    C2B C1B C11B . . 120.5(3) ?
    O21B C2B C3B . . 123.8(3) ?
    O21B C2B C1B . . 115.8(3) ?
    C3B C2B C1B . . 120.4(4) ?
    C4B C3B C2B . . 120.1(4) ?
    C4B C3B H3B . . 119.9 ?
    C2B C3B H3B . . 119.9 ?
    C5B C4B C3B . . 120.4(5) ?
    C5B C4B H4B . . 119.8 ?
    C3B C4B H4B . . 119.8 ?
    C4B C5B C6B . . 119.5(4) ?
    C4B C5B H5B . . 120.2 ?
    C6B C5B H5B . . 120.2 ?
    C1B C6B C5B . . 121.8(4) ?
    C1B C6B H6B . . 119.1 ?
    C5B C6B H6B . . 119.1 ?
    C12B C11B C1B . . 127.1(4) ?
    C12B C11B H11B . . 116.4 ?
    C1B C11B H11B . . 116.4 ?
    C11B C12B C13B . . 122.9(4) ?
    C11B C12B H12B . . 118.6 ?
    C13B C12B H12B . . 118.6 ?
    O12B C13B O11B . . 123.2(4) ?
    O12B C13B C12B . . 120.9(3) ?
    O11B C13B C12B . . 115.9(4) ?
    O21B C21B C22B . . 107.1(3) ?
    O21B C21B H21E . . 110.3 ?
    C22B C21B H21E . . 110.3 ?
    O21B C21B H21F . . 110.3 ?
    C22B C21B H21F . . 110.3 ?
    H21E C21B H21F . . 108.5 ?
    C21B C22B H22G . . 109.5 ?
    C21B C22B H22H . . 109.5 ?
    H22G C22B H22H . . 109.5 ?
    C21B C22B H22I . . 109.5 ?
    H22G C22B H22I . . 109.5 ?
    H22H C22B H22I . . 109.5 ?
    C13B O11B H1B . . 109.5 ?
    C2B O21B C21B . . 118.6(3) ?
    C2C C1C C6C . . 118.7(3) ?
    C2C C1C C11C . . 119.7(3) ?
    C6C C1C C11C . . 121.5(3) ?
    O21C C2C C1C . . 116.5(3) ?
    O21C C2C C3C . . 122.9(3) ?
    C1C C2C C3C . . 120.6(3) ?
    C4C C3C C2C . . 119.3(4) ?
    C4C C3C H3C . . 120.4 ?
    C2C C3C H3C . . 120.4 ?
    C5C C4C C3C . . 120.4(4) ?
    C5C C4C H4C . . 119.8 ?
    C3C C4C H4C . . 119.8 ?
    C6C C5C C4C . . 120.0(4) ?
    C6C C5C H5C . . 120.0 ?
    C4C C5C H5C . . 120.0 ?
    C5C C6C C1C . . 120.9(4) ?
    C5C C6C H6C . . 119.5 ?
    C1C C6C H6C . . 119.5 ?
    C12C C11C C1C . . 127.6(3) ?
    C12C C11C H11C . . 116.2 ?
    C1C C11C H11C . . 116.2 ?
    C11C C12C C13C . . 122.7(3) ?
    C11C C12C H12C . . 118.7 ?
    C13C C12C H12C . . 118.7 ?
    O12C C13C O11C . . 123.0(4) ?
    O12C C13C C12C . . 121.4(3) ?
    O11C C13C C12C . . 115.6(4) ?
    O21C C21C C22C . . 106.9(3) ?
    O21C C21C H21A . . 110.3 ?
    C22C C21C H21A . . 110.3 ?
    O21C C21C H21B . . 110.3 ?
    C22C C21C H21B . . 110.3 ?
    H21A C21C H21B . . 108.6 ?
    C21C C22C H22A . . 109.5 ?
    C21C C22C H22B . . 109.5 ?
    H22A C22C H22B . . 109.5 ?
    C21C C22C H22C . . 109.5 ?
    H22A C22C H22C . . 109.5 ?
    H22B C22C H22C . . 109.5 ?
    C13C O11C H1C . . 109.5 ?
    C2C O21C C21C . . 119.0(3) ?
    C2D C1D C6D . . 117.6 ?
    C2D C1D C11D . . 116.5 ?
    C6D C1D C11D . . 125.3 ?
    O21D C2D C1D . . 115.0 ?
    O21D C2D C3D . . 124.0 ?
    C1D C2D C3D . . 121.0 ?
    C4D C3D C2D . . 118.8 ?
    C4D C3D H3D . . 120.6 ?
    C2D C3D H3D . . 120.6 ?
    C5D C4D C3D . . 121.6 ?
    C5D C4D H4D . . 119.2 ?
    C3D C4D H4D . . 119.2 ?
    C4D C5D C6D . . 118.6 ?
    C4D C5D H5D . . 120.7 ?
    C6D C5D H5D . . 120.7 ?
    C5D C6D C1D . . 122.5 ?
    C5D C6D H6D . . 118.7 ?
    C1D C6D H6D . . 118.7 ?
    C1D C11D C12D . . 119.2 ?
    C1D C11D C12E . . 116.5 ?
    C12D C11D C12E . . 89.6 ?
    C1D C11D H11D . . 110.0 ?
    C12D C11D H11D . . 110.0 ?
    C12E C11D H11D . . 110.0 ?
    C13D C12D C11D . . 114.6 ?
    C13D C12D C11E . . 112.4 ?
    C11D C12D C11E . . 90.4 ?
    C13D C12D H12D . . 112.6 ?
    C11D C12D H12D . . 112.6 ?
    C11E C12D H12D . . 112.6 ?
    O12D C13D O11D . . 122.4 ?
    O12D C13D C12D . . 124.0 ?
    O11D C13D C12D . . 113.0 ?
    O21D C21D C22D . . 107.7 ?
    O21D C21D H21G . . 110.2 ?
    C22D C21D H21G . . 110.2 ?
    O21D C21D H21H . . 110.2 ?
    C22D C21D H21H . . 110.2 ?
    H21G C21D H21H . . 108.5 ?
    C21D C22D H22J . . 109.5 ?
    C21D C22D H22K . . 109.5 ?
    H22J C22D H22K . . 109.5 ?
    C21D C22D H22L . . 109.5 ?
    H22J C22D H22L . . 109.5 ?
    H22K C22D H22L . . 109.5 ?
    C13D O11D H1D . . 109.5 ?
    C2D O21D C21D . . 118.0 ?
    C2E C1E C6E . . 118.5 ?
    C2E C1E C11E . . 115.6 ?
    C6E C1E C11E . . 124.9 ?
    C1E C2E O21E . . 115.2 ?
    C1E C2E C3E . . 120.7 ?
    O21E C2E C3E . . 124.1 ?
    C4E C3E C2E . . 119.0 ?
    C4E C3E H3E . . 120.5 ?
    C2E C3E H3E . . 120.5 ?
    C5E C4E C3E . . 121.3 ?
    C5E C4E H4E . . 119.4 ?
    C3E C4E H4E . . 119.4 ?
    C4E C5E C6E . . 119.0 ?
    C4E C5E H5E . . 120.5 ?
    C6E C5E H5E . . 120.5 ?
    C5E C6E C1E . . 121.6 ?
    C5E C6E H6E . . 119.2 ?
    C1E C6E H6E . . 119.2 ?
    C1E C11E C12E . . 119.6 ?
    C1E C11E C12D . . 116.7 ?
    C12E C11E C12D . . 89.9 ?
    C1E C11E H11E . . 109.7 ?
    C12E C11E H11E . . 109.7 ?
    C12D C11E H11E . . 109.7 ?
    C13E C12E C11E . . 115.4 ?
    C13E C12E C11D . . 112.1 ?
    C11E C12E C11D . . 90.1 ?
    C13E C12E H12E . . 112.5 ?
    C11E C12E H12E . . 112.5 ?
    C11D C12E H12E . . 112.5 ?
    O12E C13E O11E . . 123.8 ?
    O12E C13E C12E . . 123.0 ?
    O11E C13E C12E . . 112.5 ?
    O21E C21E C22E . . 107.3 ?
    O21E C21E H21I . . 110.3 ?
    C22E C21E H21I . . 110.3 ?
    O21E C21E H21J . . 110.3 ?
    C22E C21E H21J . . 110.3 ?
    H21I C21E H21J . . 108.5 ?
    C21E C22E H22M . . 109.5 ?
    C21E C22E H22N . . 109.5 ?
    H22M C22E H22N . . 109.5 ?
    C21E C22E H22O . . 109.5 ?
    H22M C22E H22O . . 109.5 ?
    H22N C22E H22O . . 109.5 ?
    C13E O11E H1E . . 109.5 ?
    C2E O21E C21E . . 117.6 ?
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C6A C1A C2A O21A . . . . -179.4(3) ?
    C11A C1A C2A O21A . . . . -0.8(5) ?
    C6A C1A C2A C3A . . . . 1.1(6) ?
    C11A C1A C2A C3A . . . . 179.7(4) ?
    O21A C2A C3A C4A . . . . 179.5(4) ?
    C1A C2A C3A C4A . . . . -1.1(6) ?
    C2A C3A C4A C5A . . . . 1.5(7) ?
    C3A C4A C5A C6A . . . . -1.9(7) ?
    C4A C5A C6A C1A . . . . 2.0(7) ?
    C2A C1A C6A C5A . . . . -1.6(6) ?
    C11A C1A C6A C5A . . . . 179.9(4) ?
    C6A C1A C11A C12A . . . . 0.4(6) ?
    C2A C1A C11A C12A . . . . -178.1(4) ?
    C1A C11A C12A C13A . . . . 179.8(4) ?
    C11A C12A C13A O11A . . . . 180.0(4) ?
    C11A C12A C13A O12A . . . . -0.3(6) ?
    C3A C2A O21A C21A . . . . 1.5(6) ?
    C1A C2A O21A C21A . . . . -177.9(3) ?
    C22A C21A O21A C2A . . . . 175.8(3) ?
    C6B C1B C2B O21B . . . . 179.9(3) ?
    C11B C1B C2B O21B . . . . 1.9(5) ?
    C6B C1B C2B C3B . . . . -1.9(5) ?
    C11B C1B C2B C3B . . . . -180.0(3) ?
    O21B C2B C3B C4B . . . . 179.5(4) ?
    C1B C2B C3B C4B . . . . 1.5(6) ?
    C2B C3B C4B C5B . . . . -1.0(7) ?
    C3B C4B C5B C6B . . . . 0.9(7) ?
    C2B C1B C6B C5B . . . . 1.8(6) ?
    C11B C1B C6B C5B . . . . 179.8(4) ?
    C4B C5B C6B C1B . . . . -1.3(7) ?
    C6B C1B C11B C12B . . . . 8.8(6) ?
    C2B C1B C11B C12B . . . . -173.2(4) ?
    C1B C11B C12B C13B . . . . -179.7(3) ?
    C11B C12B C13B O12B . . . . 6.4(6) ?
    C11B C12B C13B O11B . . . . -173.8(3) ?
    C3B C2B O21B C21B . . . . -0.1(5) ?
    C1B C2B O21B C21B . . . . 178.0(3) ?
    C22B C21B O21B C2B . . . . -177.7(3) ?
    C6C C1C C2C O21C . . . . -180.0(3) ?
    C11C C1C C2C O21C . . . . -1.0(4) ?
    C6C C1C C2C C3C . . . . -0.4(5) ?
    C11C C1C C2C C3C . . . . 178.6(3) ?
    O21C C2C C3C C4C . . . . 179.5(3) ?
    C1C C2C C3C C4C . . . . -0.1(6) ?
    C2C C3C C4C C5C . . . . 0.7(6) ?
    C3C C4C C5C C6C . . . . -0.9(6) ?
    C4C C5C C6C C1C . . . . 0.5(6) ?
    C2C C1C C6C C5C . . . . 0.2(5) ?
    C11C C1C C6C C5C . . . . -178.8(3) ?
    C2C C1C C11C C12C . . . . -177.8(3) ?
    C6C C1C C11C C12C . . . . 1.1(5) ?
    C1C C11C C12C C13C . . . . 178.9(3) ?
    C11C C12C C13C O12C . . . . 5.2(5) ?
    C11C C12C C13C O11C . . . . -176.2(3) ?
    C1C C2C O21C C21C . . . . 175.8(3) ?
    C3C C2C O21C C21C . . . . -3.8(5) ?
    C22C C21C O21C C2C . . . . -174.0(3) ?
    C6D C1D C2D O21D . . . . 179.8 ?
    C11D C1D C2D O21D . . . . 8.7 ?
    C6D C1D C2D C3D . . . . -1.6 ?
    C11D C1D C2D C3D . . . . -172.7 ?
    O21D C2D C3D C4D . . . . -179.8 ?
    C1D C2D C3D C4D . . . . 1.7 ?
    C2D C3D C4D C5D . . . . -1.5 ?
    C3D C4D C5D C6D . . . . 1.1 ?
    C4D C5D C6D C1D . . . . -1.0 ?
    C2D C1D C6D C5D . . . . 1.3 ?
    C11D C1D C6D C5D . . . . 171.5 ?
    C2D C1D C11D C12D . . . . -176.6 ?
    C6D C1D C11D C12D . . . . 13.1 ?
    C2D C1D C11D C12E . . . . 77.8 ?
    C6D C1D C11D C12E . . . . -92.6 ?
    C1D C11D C12D C13D . . . . 125.2 ?
    C12E C11D C12D C13D . . . . -114.3 ?
    C1D C11D C12D C11E . . . . -119.8 ?
    C12E C11D C12D C11E . . . . 0.7 ?
    C11D C12D C13D O12D . . . . 31.8 ?
    C11E C12D C13D O12D . . . . -69.5 ?
    C11D C12D C13D O11D . . . . -157.0 ?
    C11E C12D C13D O11D . . . . 101.6 ?
    C1D C2D O21D C21D . . . . -169.1 ?
    C3D C2D O21D C21D . . . . 12.3 ?
    C22D C21D O21D C2D . . . . 174.3 ?
    C6E C1E C2E O21E . . . . 179.2 ?
    C11E C1E C2E O21E . . . . -11.3 ?
    C6E C1E C2E C3E . . . . 0.2 ?
    C11E C1E C2E C3E . . . . 169.8 ?
    C1E C2E C3E C4E . . . . 0.1 ?
    O21E C2E C3E C4E . . . . -178.7 ?
    C2E C3E C4E C5E . . . . 0.0 ?
    C3E C4E C5E C6E . . . . -0.5 ?
    C4E C5E C6E C1E . . . . 0.9 ?
    C2E C1E C6E C5E . . . . -0.7 ?
    C11E C1E C6E C5E . . . . -169.2 ?
    C2E C1E C11E C12E . . . . -176.1 ?
    C6E C1E C11E C12E . . . . -7.4 ?
    C2E C1E C11E C12D . . . . -69.7 ?
    C6E C1E C11E C12D . . . . 99.1 ?
    C13D C12D C11E C1E . . . . -7.3 ?
    C11D C12D C11E C1E . . . . -124.2 ?
    C13D C12D C11E C12E . . . . 116.2 ?
    C11D C12D C11E C12E . . . . -0.7 ?
    C1E C11E C12E C13E . . . . -123.6 ?
    C12D C11E C12E C13E . . . . 115.4 ?
    C1E C11E C12E C11D . . . . 121.7 ?
    C12D C11E C12E C11D . . . . 0.7 ?
    C1D C11D C12E C13E . . . . 4.5 ?
    C12D C11D C12E C13E . . . . -118.3 ?
    C1D C11D C12E C11E . . . . 122.1 ?
    C12D C11D C12E C11E . . . . -0.7 ?
    C11E C12E C13E O12E . . . . -23.8 ?
    C11D C12E C13E O12E . . . . 77.5 ?
    C11E C12E C13E O11E . . . . 165.0 ?
    C11D C12E C13E O11E . . . . -93.7 ?
    C1E C2E O21E C21E . . . . 165.9 ?
    C3E C2E O21E C21E . . . . -15.2 ?
    C22E C21E O21E C2E . . . . -171.1 ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    O11C H1C O12B 2_766 0.82 1.81 2.618(4) 166.2
    O11B H1B O12C 2_766 0.82 1.79 2.593(4) 167.2
    O12A H1A O11A 2_655 0.82 1.77 2.578(6) 170.2
data_d6hlt_s
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2003-11-12
_journal_date_accepted     2004-04-15
_journal_name_full     'Acta Crystallographica, Section B'
_journal_year     2004
_journal_volume     60
_journal_issue      3
_journal_page_first     300
_journal_page_last     314
_journal_paper_category     FA
_chemical_name_systematic
;
  (E)-3-(2-Ethoxyphenyl)propenoic acid and
trans-2,4-bis(2-ethoxyphenyl)-trans-1,3-cyclobutane-dicarboxylic acid
;
_chemical_name_common
;
ortho-ethoxy-trans-cinnamic acid and 2,2'-diethoxy alpha-truxillic acid
;
_chemical_formula_moiety     '0.124(C22 H24 O6), 2.752(C11 H12 O3)'
_chemical_formula_sum     'C33 H36 O9'
_chemical_formula_weight     576.62
_chemical_melting_point     ?
_symmetry_cell_setting     Triclinic
_symmetry_space_group_name_H-M     P-1
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     8.6452(13)
_cell_length_b     10.8577(17)
_cell_length_c     17.262(3)
_cell_angle_alpha     92.470(3)
_cell_angle_beta     92.102(3)
_cell_angle_gamma     112.563(3)
_cell_volume     1492.4(4)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     728
_cell_measurement_theta_min     2.37
_cell_measurement_theta_max     26.28
_cell_measurement_temperature     173(2)
_exptl_crystal_description     irregular
_exptl_crystal_colour     white
_exptl_crystal_size_max     0.38
_exptl_crystal_size_mid     0.33
_exptl_crystal_size_min     0.24
_exptl_crystal_density_diffrn     1.283
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     612
_exptl_absorpt_coefficient_mu     0.093
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_exptl_special_details
;
The following alerts are triggered when using the ACTA-C CIF validation
software:
PLAT301_ALERT_3_B Main Residue  Disorder ......................... 40.00 Perc.
PLAT432_ALERT_2_B Short Inter X...Y Contact  C3C    ..  C4D     ..  3.09 Ang.
PLAT432_ALERT_2_B Short Inter X...Y Contact  C4C    ..  C3D     ..  3.07 Ang.
PLAT165_ALERT_3_C Nr. of Status R Flagged Non-Hydrogen Atoms .....     28
PLAT432_ALERT_2_C Short Inter X...Y Contact  C3C    ..  C3D     ..  3.18 Ang.
------
Authors comment: The assymetric unit consists of a mixture of the monomer
and dimer. The short contacts are most probably due to the dimer not being
properly optimised for the crystal structure at this point. Coordinates
for the dimer molecule at a higher conversion stage was used as a starting
point for the refinement. The dimer was also refined isotropically
as a rigid body. This is necessary as the dimer is only present in about 4-5%
occupancy (4% dimer occupancy = 8% of monomer consumed).
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....       ?
------
Authors commment: Our moiety formula is correct as it takes the occupancy
of the dimer and monomer molecules into account.
;
_diffrn_ambient_temperature     173(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART 1K'
_diffrn_measurement_method     'phi and omega scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     8177
_diffrn_reflns_av_R_equivalents     0.0220
_diffrn_reflns_av_sigmaI/netI     0.0525
_diffrn_reflns_theta_min     1.18
_diffrn_reflns_theta_max     25.49
_diffrn_reflns_theta_full     25.49
_diffrn_measured_fraction_theta_max     0.990
_diffrn_measured_fraction_theta_full     0.990
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     8
_diffrn_reflns_limit_k_min     -13
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     -20
_diffrn_reflns_limit_l_max     20
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     5500
_reflns_number_gt     3167
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1075
_refine_ls_R_factor_gt     0.0530
_refine_ls_wR_factor_gt     0.1170
_refine_ls_wR_factor_ref     0.1357
_refine_ls_goodness_of_fit_ref     1.033
_refine_ls_restrained_S_all     1.033
_refine_ls_number_reflns     5500
_refine_ls_number_parameters     390
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0572P)²+0.0749P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.139
_refine_diff_density_min     -0.209
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 0.0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0106 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'SMART-NT (Bruker, 1998)'
_computing_cell_refinement     'SAINT+(Bruker, 1999a)'
_computing_data_reduction     'SAINT+(Bruker, 1999a)'
_computing_structure_solution     'SHELXTL (Bruker, 1999b)'
_computing_structure_refinement     'SHELXTL (Bruker, 1999b)'
_computing_molecular_graphics
;
PLATON (Spek, 2003), SHELXTL (Bruker, 1999b),
SCHAKAL-97 (Keller, 1997) and DS ViewerPro (Accelrys, 2002)
;
_computing_publication_material     'SHELXTL (Bruker, 1999b)'
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
    C1A 1.0162(3) 0.0296(2) 0.22157(15) 0.0409(7) Uani d P 0.876(2) A 2 C
    C2A 1.0094(4) 0.0241(3) 0.30238(15) 0.0419(7) Uani d P 0.876(2) A 2 C
    C3A 1.1499(4) 0.0338(3) 0.34793(17) 0.0495(8) Uani d P 0.876(2) A 2 C
    H3A 1.1454 0.0318 0.4028 0.059 Uiso calc PR 0.876(2) A 2 H
    C4A 1.2960(4) 0.0462(3) 0.31332(19) 0.0562(8) Uani d P 0.876(2) A 2 C
    H4A 1.3916 0.0519 0.3445 0.067 Uiso calc PR 0.876(2) A 2 H
    C5A 1.3042(4) 0.0504(3) 0.2336(2) 0.0578(8) Uani d P 0.876(2) A 2 C
    H5A 1.4053 0.0595 0.2100 0.069 Uiso calc PR 0.876(2) A 2 H
    C6A 1.1662(4) 0.0414(3) 0.18871(17) 0.0511(8) Uani d P 0.876(2) A 2 C
    H6A 1.1725 0.0432 0.1339 0.061 Uiso calc PR 0.876(2) A 2 H
    C11A 0.8669(3) 0.0204(2) 0.17418(14) 0.0431(7) Uani d P 0.876(2) A 2 C
    H11A 0.7711 0.0140 0.2016 0.052 Uiso calc PR 0.876(2) A 2 H
    C12A 0.8511(4) 0.0198(2) 0.09700(14) 0.0458(7) Uani d P 0.876(2) A 2 C
    H12A 0.9449 0.0270 0.0678 0.055 Uiso calc PR 0.876(2) A 2 H
    C13A 0.6963(4) 0.0087(2) 0.05566(15) 0.0453(7) Uani d P 0.876(2) A 2 C
    C21A 0.8459(4) 0.0094(3) 0.41466(14) 0.0461(7) Uani d P 0.876(2) A 2 C
    H21C 0.9338 0.0898 0.4412 0.055 Uiso calc PR 0.876(2) A 2 H
    H21D 0.8592 -0.0708 0.4338 0.055 Uiso calc PR 0.876(2) A 2 H
    C22A 0.6753(4) 0.0064(3) 0.43047(16) 0.0522(8) Uani d P 0.876(2) A 2 C
    H22D 0.6661 0.0886 0.4139 0.078 Uiso calc PR 0.876(2) A 2 H
    H22E 0.6586 -0.0005 0.4862 0.078 Uiso calc PR 0.876(2) A 2 H
    H22F 0.5897 -0.0709 0.4016 0.078 Uiso calc PR 0.876(2) A 2 H
    O11A 0.6924(2) 0.01017(19) -0.01746(11) 0.0515(6) Uani d P 0.876(2) A 2 O
    O12A 0.5693(3) -0.0032(2) 0.09562(12) 0.0584(6) Uani d P 0.876(2) A 2 O
    H1A 0.4880 -0.0083 0.0657 0.088 Uiso calc PR 0.876(2) A 2 H
    O21A 0.8599(3) 0.0121(2) 0.33185(10) 0.0461(5) Uani d P 0.876(2) A 2 O
    C1B 0.7885(3) 0.3467(2) 0.12841(14) 0.0335(6) Uani d P 0.876(2) A 2 C
    C2B 0.7885(3) 0.3357(2) 0.04688(14) 0.0335(6) Uani d P 0.876(2) A 2 C
    C3B 0.6507(3) 0.3319(3) 0.00137(16) 0.0429(7) Uani d P 0.876(2) A 2 C
    H3B 0.6512 0.3246 -0.0537 0.051 Uiso calc PR 0.876(2) A 2 H
    C4B 0.5132(4) 0.3388(3) 0.03635(18) 0.0509(8) Uani d P 0.876(2) A 2 C
    H4B 0.4188 0.3355 0.0051 0.061 Uiso calc PR 0.876(2) A 2 H
    C5B 0.5107(4) 0.3504(3) 0.11661(19) 0.0505(8) Uani d P 0.876(2) A 2 C
    H5B 0.4157 0.3555 0.1403 0.061 Uiso calc PR 0.876(2) A 2 H
    C6B 0.6481(3) 0.3544(3) 0.16136(15) 0.0417(7) Uani d P 0.876(2) A 2 C
    H6B 0.6467 0.3626 0.2163 0.050 Uiso calc PR 0.876(2) A 2 H
    C11B 0.9351(3) 0.3525(2) 0.17578(13) 0.0362(6) Uani d P 0.876(2) A 2 C
    H11B 1.0318 0.3591 0.1489 0.043 Uiso calc PR 0.876(2) A 2 H
    C12B 0.9469(3) 0.3493(2) 0.25290(13) 0.0408(7) Uani d P 0.876(2) A 2 C
    H12B 0.8521 0.3422 0.2814 0.049 Uiso calc PR 0.876(2) A 2 H
    C13B 1.1002(4) 0.3566(2) 0.29525(14) 0.0403(6) Uani d P 0.876(2) A 2 C
    C21B 0.9331(3) 0.3141(3) -0.06611(13) 0.0354(6) Uani d P 0.876(2) A 2 C
    H21E 0.9263 0.3928 -0.0906 0.043 Uiso calc PR 0.876(2) A 2 H
    H21F 0.8372 0.2333 -0.0871 0.043 Uiso calc PR 0.876(2) A 2 H
    C22B 1.0954(4) 0.3014(3) -0.08263(15) 0.0448(7) Uani d P 0.876(2) A 2 C
    H22G 1.1891 0.3847 -0.0654 0.067 Uiso calc PR 0.876(2) A 2 H
    H22H 1.0987 0.2837 -0.1386 0.067 Uiso calc PR 0.876(2) A 2 H
    H22I 1.1045 0.2275 -0.0548 0.067 Uiso calc PR 0.876(2) A 2 H
    O11B 1.0898(2) 0.34100(19) 0.36854(10) 0.0481(5) Uani d P 0.876(2) A 2 O
    H1B 1.1827 0.3460 0.3880 0.072 Uiso calc PR 0.876(2) A 2 H
    O12B 1.2329(3) 0.3776(2) 0.26032(11) 0.0467(5) Uani d P 0.876(2) A 2 O
    O21B 0.9293(2) 0.32927(19) 0.01674(10) 0.0383(5) Uani d P 0.876(2) A 2 O
    C1C 0.2212(3) 0.6717(2) 0.42538(12) 0.0383(5) Uani d . 1 . . C
    C2C 0.2336(3) 0.6865(2) 0.34524(12) 0.0387(5) Uani d . 1 . . C
    C3C 0.1000(3) 0.6899(2) 0.29955(14) 0.0519(6) Uani d . 1 . . C
    H3C 0.1096 0.7004 0.2454 0.062 Uiso calc R 1 . . H
    C4C -0.0476(3) 0.6779(3) 0.33352(15) 0.0573(7) Uani d . 1 . . C
    H4C -0.1396 0.6791 0.3022 0.069 Uiso calc R 1 . . H
    C5C -0.0623(3) 0.6642(2) 0.41232(15) 0.0536(7) Uani d . 1 . . C
    H5C -0.1636 0.6567 0.4352 0.064 Uiso calc R 1 . . H
    C6C 0.0706(3) 0.6614(2) 0.45758(13) 0.0467(6) Uani d . 1 . . C
    H6C 0.0600 0.6522 0.5118 0.056 Uiso calc R 1 . . H
    C11C 0.3617(3) 0.66488(19) 0.47177(12) 0.0386(5) Uani d . 1 . . C
    H11C 0.4601 0.6754 0.4454 0.046 Uiso calc R 1 . . H
    C12C 0.3664(3) 0.6453(2) 0.54770(12) 0.0444(6) Uani d . 1 . . C
    H12C 0.2711 0.6359 0.5762 0.053 Uiso calc R 1 . . H
    C13C 0.5136(3) 0.6378(2) 0.58787(12) 0.0430(6) Uani d . 1 . . C
    C21C 0.3994(3) 0.7040(2) 0.23407(11) 0.0406(6) Uani d . 1 . . C
    H21A 0.3936 0.7882 0.2171 0.049 Uiso calc R 1 . . H
    H21B 0.3084 0.6279 0.2057 0.049 Uiso calc R 1 . . H
    C22C 0.5668(3) 0.6999(2) 0.21845(12) 0.0456(6) Uani d . 1 . . C
    H22A 0.6551 0.7730 0.2491 0.068 Uiso calc R 1 . . H
    H22B 0.5862 0.7099 0.1631 0.068 Uiso calc R 1 . . H
    H22C 0.5686 0.6142 0.2330 0.068 Uiso calc R 1 . . H
    O11C 0.49716(19) 0.61046(16) 0.65985(8) 0.0557(5) Uani d . 1 . . O
    H1C 0.5869 0.6081 0.6787 0.084 Uiso calc R 1 . . H
    O12C 0.6474(2) 0.65866(16) 0.55414(8) 0.0515(4) Uani d . 1 . . O
    O21C 0.38280(17) 0.69618(15) 0.31622(8) 0.0435(4) Uani d . 1 . . O
    C1D 1.0226(10) 0.0482(7) 0.2390(4) 0.0386(17) Uiso d PG 0.124(2) A 1 C
    C2D 1.0064(12) 0.0102(8) 0.3149(4) 0.0386(17) Uiso d PG 0.124(2) A 1 C
    C3D 1.1339(14) -0.0175(10) 0.3546(5) 0.0386(17) Uiso d PG 0.124(2) A 1 C
    H3D 1.1208 -0.0458 0.4062 0.046 Uiso calc PR 0.124(2) A 1 H
    C4D 1.2788(14) -0.0024(12) 0.3171(6) 0.0386(17) Uiso d PG 0.124(2) A 1 C
    H4D 1.3662 -0.0188 0.3439 0.046 Uiso calc PR 0.124(2) A 1 H
    C5D 1.2986(13) 0.0354(12) 0.2424(6) 0.0386(17) Uiso d PG 0.124(2) A 1 C
    H5D 1.3976 0.0438 0.2170 0.046 Uiso calc PR 0.124(2) A 1 H
    C6D 1.1710(11) 0.0613(9) 0.2043(5) 0.0386(17) Uiso d PG 0.124(2) A 1 C
    H6D 1.1853 0.0890 0.1526 0.046 Uiso calc PR 0.124(2) A 1 H
    C11D 0.8902(8) 0.0913(5) 0.2057(4) 0.0386(17) Uiso d PG 0.124(2) A 1 C
    H11D 0.7763 0.0248 0.2159 0.046 Uiso calc PR 0.124(2) A 1 H
    C12D 0.8950(8) 0.1272(6) 0.1203(3) 0.0386(17) Uiso d PG 0.124(2) A 1 C
    H12D 0.9967 0.1256 0.0952 0.046 Uiso calc PR 0.124(2) A 1 H
    C13D 0.7324(10) 0.0497(7) 0.0709(4) 0.0386(17) Uiso d PG 0.124(2) A 1 C
    C21D 0.8448(16) -0.0161(12) 0.4273(5) 0.0386(17) Uiso d PG 0.124(2) A 1 C
    H21G 0.9383 0.0568 0.4566 0.046 Uiso calc PR 0.124(2) A 1 H
    H21H 0.8496 -0.1024 0.4404 0.046 Uiso calc PR 0.124(2) A 1 H
    C22D 0.6783(16) -0.0116(15) 0.4483(5) 0.0386(17) Uiso d PG 0.124(2) A 1 C
    H22J 0.6655 -0.0219 0.5041 0.058 Uiso calc PR 0.124(2) A 1 H
    H22K 0.5867 -0.0843 0.4191 0.058 Uiso calc PR 0.124(2) A 1 H
    H22L 0.6750 0.0744 0.4352 0.058 Uiso calc PR 0.124(2) A 1 H
    O11D 0.7562(13) 0.0444(9) -0.0043(4) 0.0386(17) Uiso d PG 0.124(2) A 1 O
    H11E 0.6641 0.0012 -0.0289 0.058 Uiso calc PR 0.124(2) A 1 H
    O12D 0.5934(9) 0.0114(8) 0.0960(5) 0.0386(17) Uiso d PG 0.124(2) A 1 O
    O21D 0.8584(12) -0.0007(9) 0.3461(4) 0.0386(17) Uiso d PG 0.124(2) A 1 O
    C1E 0.7828(11) 0.3225(7) 0.1120(5) 0.0386(17) Uiso d PG 0.124(2) A 1 C
    C2E 0.7926(13) 0.3444(8) 0.0336(5) 0.0386(17) Uiso d PG 0.124(2) A 1 C
    C3E 0.6643(15) 0.3668(11) -0.0075(6) 0.0386(17) Uiso d PG 0.124(2) A 1 C
    H3E 0.6712 0.3817 -0.0613 0.046 Uiso calc PR 0.124(2) A 1 H
    C4E 0.5264(15) 0.3669(13) 0.0317(7) 0.0386(17) Uiso d PG 0.124(2) A 1 C
    H4E 0.4388 0.3820 0.0041 0.046 Uiso calc PR 0.124(2) A 1 H
    C5E 0.5146(14) 0.3458(13) 0.1091(7) 0.0386(17) Uiso d PG 0.124(2) A 1 C
    H5E 0.4203 0.3468 0.1353 0.046 Uiso calc PR 0.124(2) A 1 H
    C6E 0.6424(12) 0.3228(10) 0.1488(5) 0.0386(17) Uiso d PG 0.124(2) A 1 C
    H6E 0.6338 0.3068 0.2025 0.046 Uiso calc PR 0.124(2) A 1 H
    C11E 0.9126(9) 0.2761(6) 0.1467(4) 0.0386(17) Uiso d PG 0.124(2) A 1 C
    H11F 1.0277 0.3412 0.1370 0.046 Uiso calc PR 0.124(2) A 1 H
    C12E 0.9055(9) 0.2403(6) 0.2322(4) 0.0386(17) Uiso d PG 0.124(2) A 1 C
    H12E 0.8023 0.2408 0.2562 0.046 Uiso calc PR 0.124(2) A 1 H
    C13E 1.0645(11) 0.3168(7) 0.2831(4) 0.0386(17) Uiso d PG 0.124(2) A 1 C
    C21E 0.9380(16) 0.3355(12) -0.0822(4) 0.0386(17) Uiso d PG 0.124(2) A 1 C
    H21I 0.9374 0.4185 -0.1035 0.046 Uiso calc PR 0.124(2) A 1 H
    H21J 0.8374 0.2594 -0.1042 0.046 Uiso calc PR 0.124(2) A 1 H
    C22E 1.0965(16) 0.3150(15) -0.1027(5) 0.0386(17) Uiso d PG 0.124(2) A 1 C
    H22M 1.1011 0.3084 -0.1593 0.058 Uiso calc PR 0.124(2) A 1 H
    H22N 1.0954 0.2325 -0.0813 0.058 Uiso calc PR 0.124(2) A 1 H
    H22O 1.1950 0.3910 -0.0806 0.058 Uiso calc PR 0.124(2) A 1 H
    O11E 1.0396(14) 0.3063(9) 0.3571(4) 0.0386(17) Uiso d PG 0.124(2) A 1 O
    H11G 1.1299 0.3497 0.3830 0.058 Uiso calc PR 0.124(2) A 1 H
    O12E 1.2033(10) 0.3675(7) 0.2571(5) 0.0386(17) Uiso d PG 0.124(2) A 1 O
    O21E 0.9371(13) 0.3445(9) 0.0012(4) 0.0386(17) Uiso d PG 0.124(2) A 1 O
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
    C1A C6A . 1.397(4) ?
    C1A C2A . 1.401(3) ?
    C1A C11A . 1.470(4) ?
    C2A O21A . 1.368(3) ?
    C2A C3A . 1.389(4) ?
    C3A C4A . 1.379(4) ?
    C3A H3A . 0.9500 ?
    C4A C5A . 1.383(4) ?
    C4A H4A . 0.9500 ?
    C5A C6A . 1.366(4) ?
    C5A H5A . 0.9500 ?
    C6A H6A . 0.9500 ?
    C11A C12A . 1.334(3) ?
    C11A H11A . 0.9500 ?
    C12A C13A . 1.454(4) ?
    C12A H12A . 0.9500 ?
    C13A O11A . 1.262(3) ?
    C13A O12A . 1.285(3) ?
    C21A O21A . 1.440(3) ?
    C21A C22A . 1.497(3) ?
    C21A H21C . 0.9900 ?
    C21A H21D . 0.9900 ?
    C22A H22D . 0.9800 ?
    C22A H22E . 0.9800 ?
    C22A H22F . 0.9800 ?
    O12A H1A . 0.8400 ?
    C1B C6B . 1.389(3) ?
    C1B C2B . 1.407(3) ?
    C1B C11B . 1.462(3) ?
    C2B O21B . 1.366(3) ?
    C2B C3B . 1.389(3) ?
    C3B C4B . 1.379(3) ?
    C3B H3B . 0.9500 ?
    C4B C5B . 1.387(4) ?
    C4B H4B . 0.9500 ?
    C5B C6B . 1.378(4) ?
    C5B H5B . 0.9500 ?
    C6B H6B . 0.9500 ?
    C11B C12B . 1.334(3) ?
    C11B H11B . 0.9500 ?
    C12B C13B . 1.463(3) ?
    C12B H12B . 0.9500 ?
    C13B O12B . 1.262(3) ?
    C13B O11B . 1.285(3) ?
    C21B O21B . 1.436(3) ?
    C21B C22B . 1.497(3) ?
    C21B H21E . 0.9900 ?
    C21B H21F . 0.9900 ?
    C22B H22G . 0.9800 ?
    C22B H22H . 0.9800 ?
    C22B H22I . 0.9800 ?
    O11B H1B . 0.8400 ?
    C1C C6C . 1.401(3) ?
    C1C C2C . 1.403(3) ?
    C1C C11C . 1.458(3) ?
    C2C O21C . 1.369(2) ?
    C2C C3C . 1.388(3) ?
    C3C C4C . 1.387(3) ?
    C3C H3C . 0.9500 ?
    C4C C5C . 1.380(3) ?
    C4C H4C . 0.9500 ?
    C5C C6C . 1.377(3) ?
    C5C H5C . 0.9500 ?
    C6C H6C . 0.9500 ?
    C11C C12C . 1.339(3) ?
    C11C H11C . 0.9500 ?
    C12C C13C . 1.458(3) ?
    C12C H12C . 0.9500 ?
    C13C O12C . 1.260(3) ?
    C13C O11C . 1.290(2) ?
    C21C O21C . 1.433(2) ?
    C21C C22C . 1.499(3) ?
    C21C H21A . 0.9900 ?
    C21C H21B . 0.9900 ?
    C22C H22A . 0.9800 ?
    C22C H22B . 0.9800 ?
    C22C H22C . 0.9800 ?
    O11C H1C . 0.8400 ?
    C1D C2D . 1.3866 ?
    C1D C6D . 1.3961 ?
    C1D C11D . 1.4979 ?
    C2D O21D . 1.3716 ?
    C2D C3D . 1.4116 ?
    C3D C4D . 1.3884 ?
    C3D H3D . 0.9500 ?
    C4D C5D . 1.3674 ?
    C4D H4D . 0.9500 ?
    C5D C6D . 1.3890 ?
    C5D H5D . 0.9500 ?
    C6D H6D . 0.9500 ?
    C11D C12D . 1.5394 ?
    C11D C12E . 1.6166 ?
    C11D H11D . 1.0000 ?
    C12D C13D . 1.5337 ?
    C12D C11E . 1.6084 ?
    C12D H12D . 1.0000 ?
    C13D O12D . 1.2148 ?
    C13D O11D . 1.3234 ?
    C21D O21D . 1.4229 ?
    C21D C22D . 1.5151 ?
    C21D H21G . 0.9900 ?
    C21D H21H . 0.9900 ?
    C22D H22J . 0.9800 ?
    C22D H22K . 0.9800 ?
    C22D H22L . 0.9800 ?
    O11D H11E . 0.8400 ?
    C1E C2E . 1.3829 ?
    C1E C6E . 1.3919 ?
    C1E C11E . 1.5118 ?
    C2E O21E . 1.3878 ?
    C2E C3E . 1.3985 ?
    C3E C4E . 1.3933 ?
    C3E H3E . 0.9500 ?
    C4E C5E . 1.3664 ?
    C4E H4E . 0.9500 ?
    C5E C6E . 1.3865 ?
    C5E H5E . 0.9500 ?
    C6E H6E . 0.9500 ?
    C11E C12E . 1.5393 ?
    C11E H11F . 1.0000 ?
    C12E C13E . 1.5245 ?
    C12E H12E . 1.0000 ?
    C13E O12E . 1.2245 ?
    C13E O11E . 1.3047 ?
    C21E O21E . 1.4391 ?
    C21E C22E . 1.5213 ?
    C21E H21I . 0.9900 ?
    C21E H21J . 0.9900 ?
    C22E H22M . 0.9800 ?
    C22E H22N . 0.9800 ?
    C22E H22O . 0.9800 ?
    O11E H11G . 0.8400 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C6A C1A C2A . . 118.0(3) ?
    C6A C1A C11A . . 122.2(2) ?
    C2A C1A C11A . . 119.7(2) ?
    O21A C2A C3A . . 123.7(2) ?
    O21A C2A C1A . . 115.9(2) ?
    C3A C2A C1A . . 120.4(3) ?
    C4A C3A C2A . . 119.8(3) ?
    C4A C3A H3A . . 120.1 ?
    C2A C3A H3A . . 120.1 ?
    C3A C4A C5A . . 120.5(3) ?
    C3A C4A H4A . . 119.8 ?
    C5A C4A H4A . . 119.8 ?
    C6A C5A C4A . . 119.8(3) ?
    C6A C5A H5A . . 120.1 ?
    C4A C5A H5A . . 120.1 ?
    C5A C6A C1A . . 121.5(3) ?
    C5A C6A H6A . . 119.2 ?
    C1A C6A H6A . . 119.2 ?
    C12A C11A C1A . . 127.2(3) ?
    C12A C11A H11A . . 116.4 ?
    C1A C11A H11A . . 116.4 ?
    C11A C12A C13A . . 122.7(3) ?
    C11A C12A H12A . . 118.6 ?
    C13A C12A H12A . . 118.6 ?
    O11A C13A O12A . . 123.2(3) ?
    O11A C13A C12A . . 118.7(2) ?
    O12A C13A C12A . . 118.1(2) ?
    O21A C21A C22A . . 107.1(2) ?
    O21A C21A H21C . . 110.3 ?
    C22A C21A H21C . . 110.3 ?
    O21A C21A H21D . . 110.3 ?
    C22A C21A H21D . . 110.3 ?
    H21C C21A H21D . . 108.6 ?
    C21A C22A H22D . . 109.5 ?
    C21A C22A H22E . . 109.5 ?
    H22D C22A H22E . . 109.5 ?
    C21A C22A H22F . . 109.5 ?
    H22D C22A H22F . . 109.5 ?
    H22E C22A H22F . . 109.5 ?
    C13A O12A H1A . . 109.5 ?
    C2A O21A C21A . . 118.73(19) ?
    C6B C1B C2B . . 118.1(2) ?
    C6B C1B C11B . . 122.0(2) ?
    C2B C1B C11B . . 119.9(2) ?
    O21B C2B C3B . . 123.3(2) ?
    O21B C2B C1B . . 116.3(2) ?
    C3B C2B C1B . . 120.4(2) ?
    C4B C3B C2B . . 119.7(2) ?
    C4B C3B H3B . . 120.1 ?
    C2B C3B H3B . . 120.1 ?
    C3B C4B C5B . . 120.9(2) ?
    C3B C4B H4B . . 119.5 ?
    C5B C4B H4B . . 119.5 ?
    C6B C5B C4B . . 119.0(2) ?
    C6B C5B H5B . . 120.5 ?
    C4B C5B H5B . . 120.5 ?
    C5B C6B C1B . . 121.9(2) ?
    C5B C6B H6B . . 119.1 ?
    C1B C6B H6B . . 119.1 ?
    C12B C11B C1B . . 126.5(2) ?
    C12B C11B H11B . . 116.7 ?
    C1B C11B H11B . . 116.7 ?
    C11B C12B C13B . . 122.5(2) ?
    C11B C12B H12B . . 118.8 ?
    C13B C12B H12B . . 118.8 ?
    O12B C13B O11B . . 123.4(2) ?
    O12B C13B C12B . . 120.6(2) ?
    O11B C13B C12B . . 115.9(2) ?
    O21B C21B C22B . . 107.09(18) ?
    O21B C21B H21E . . 110.3 ?
    C22B C21B H21E . . 110.3 ?
    O21B C21B H21F . . 110.3 ?
    C22B C21B H21F . . 110.3 ?
    H21E C21B H21F . . 108.6 ?
    C21B C22B H22G . . 109.5 ?
    C21B C22B H22H . . 109.5 ?
    H22G C22B H22H . . 109.5 ?
    C21B C22B H22I . . 109.5 ?
    H22G C22B H22I . . 109.5 ?
    H22H C22B H22I . . 109.5 ?
    C13B O11B H1B . . 109.5 ?
    C2B O21B C21B . . 118.34(17) ?
    C6C C1C C2C . . 117.9(2) ?
    C6C C1C C11C . . 122.4(2) ?
    C2C C1C C11C . . 119.69(19) ?
    O21C C2C C3C . . 123.3(2) ?
    O21C C2C C1C . . 115.99(18) ?
    C3C C2C C1C . . 120.8(2) ?
    C2C C3C C4C . . 119.6(2) ?
    C2C C3C H3C . . 120.2 ?
    C4C C3C H3C . . 120.2 ?
    C5C C4C C3C . . 120.7(2) ?
    C5C C4C H4C . . 119.6 ?
    C3C C4C H4C . . 119.6 ?
    C6C C5C C4C . . 119.6(2) ?
    C6C C5C H5C . . 120.2 ?
    C4C C5C H5C . . 120.2 ?
    C5C C6C C1C . . 121.4(2) ?
    C5C C6C H6C . . 119.3 ?
    C1C C6C H6C . . 119.3 ?
    C12C C11C C1C . . 126.7(2) ?
    C12C C11C H11C . . 116.6 ?
    C1C C11C H11C . . 116.6 ?
    C11C C12C C13C . . 121.9(2) ?
    C11C C12C H12C . . 119.0 ?
    C13C C12C H12C . . 119.0 ?
    O12C C13C O11C . . 123.0(2) ?
    O12C C13C C12C . . 121.7(2) ?
    O11C C13C C12C . . 115.3(2) ?
    O21C C21C C22C . . 106.68(16) ?
    O21C C21C H21A . . 110.4 ?
    C22C C21C H21A . . 110.4 ?
    O21C C21C H21B . . 110.4 ?
    C22C C21C H21B . . 110.4 ?
    H21A C21C H21B . . 108.6 ?
    C21C C22C H22A . . 109.5 ?
    C21C C22C H22B . . 109.5 ?
    H22A C22C H22B . . 109.5 ?
    C21C C22C H22C . . 109.5 ?
    H22A C22C H22C . . 109.5 ?
    H22B C22C H22C . . 109.5 ?
    C13C O11C H1C . . 109.5 ?
    C2C O21C C21C . . 118.45(15) ?
    C2D C1D C6D . . 117.6 ?
    C2D C1D C11D . . 116.5 ?
    C6D C1D C11D . . 125.3 ?
    O21D C2D C1D . . 115.0 ?
    O21D C2D C3D . . 124.0 ?
    C1D C2D C3D . . 121.0 ?
    C4D C3D C2D . . 118.8 ?
    C4D C3D H3D . . 120.6 ?
    C2D C3D H3D . . 120.6 ?
    C5D C4D C3D . . 121.6 ?
    C5D C4D H4D . . 119.2 ?
    C3D C4D H4D . . 119.2 ?
    C4D C5D C6D . . 118.6 ?
    C4D C5D H5D . . 120.7 ?
    C6D C5D H5D . . 120.7 ?
    C5D C6D C1D . . 122.5 ?
    C5D C6D H6D . . 118.7 ?
    C1D C6D H6D . . 118.7 ?
    C1D C11D C12D . . 119.2 ?
    C1D C11D C12E . . 116.5 ?
    C12D C11D C12E . . 89.6 ?
    C1D C11D H11D . . 110.0 ?
    C12D C11D H11D . . 110.0 ?
    C12E C11D H11D . . 110.0 ?
    C13D C12D C11D . . 114.6 ?
    C13D C12D C11E . . 112.4 ?
    C11D C12D C11E . . 90.4 ?
    C13D C12D H12D . . 112.6 ?
    C11D C12D H12D . . 112.6 ?
    C11E C12D H12D . . 112.6 ?
    O12D C13D O11D . . 122.4 ?
    O12D C13D C12D . . 124.0 ?
    O11D C13D C12D . . 113.0 ?
    O21D C21D C22D . . 107.7 ?
    O21D C21D H21G . . 110.2 ?
    C22D C21D H21G . . 110.2 ?
    O21D C21D H21H . . 110.2 ?
    C22D C21D H21H . . 110.2 ?
    H21G C21D H21H . . 108.5 ?
    C21D C22D H22J . . 109.5 ?
    C21D C22D H22K . . 109.5 ?
    H22J C22D H22K . . 109.5 ?
    C21D C22D H22L . . 109.5 ?
    H22J C22D H22L . . 109.5 ?
    H22K C22D H22L . . 109.5 ?
    C13D O11D H11E . . 109.5 ?
    C2D O21D C21D . . 118.0 ?
    C2E C1E C6E . . 118.5 ?
    C2E C1E C11E . . 115.6 ?
    C6E C1E C11E . . 124.9 ?
    C1E C2E O21E . . 115.2 ?
    C1E C2E C3E . . 120.7 ?
    O21E C2E C3E . . 124.1 ?
    C4E C3E C2E . . 119.0 ?
    C4E C3E H3E . . 120.5 ?
    C2E C3E H3E . . 120.5 ?
    C5E C4E C3E . . 121.3 ?
    C5E C4E H4E . . 119.4 ?
    C3E C4E H4E . . 119.4 ?
    C4E C5E C6E . . 119.0 ?
    C4E C5E H5E . . 120.5 ?
    C6E C5E H5E . . 120.5 ?
    C5E C6E C1E . . 121.6 ?
    C5E C6E H6E . . 119.2 ?
    C1E C6E H6E . . 119.2 ?
    C1E C11E C12E . . 119.6 ?
    C1E C11E C12D . . 116.7 ?
    C12E C11E C12D . . 89.9 ?
    C1E C11E H11F . . 109.7 ?
    C12E C11E H11F . . 109.7 ?
    C12D C11E H11F . . 109.7 ?
    C13E C12E C11E . . 115.4 ?
    C13E C12E C11D . . 112.1 ?
    C11E C12E C11D . . 90.1 ?
    C13E C12E H12E . . 112.5 ?
    C11E C12E H12E . . 112.5 ?
    C11D C12E H12E . . 112.5 ?
    O12E C13E O11E . . 123.8 ?
    O12E C13E C12E . . 123.0 ?
    O11E C13E C12E . . 112.5 ?
    O21E C21E C22E . . 107.3 ?
    O21E C21E H21I . . 110.3 ?
    C22E C21E H21I . . 110.3 ?
    O21E C21E H21J . . 110.3 ?
    C22E C21E H21J . . 110.3 ?
    H21I C21E H21J . . 108.5 ?
    C21E C22E H22M . . 109.5 ?
    C21E C22E H22N . . 109.5 ?
    H22M C22E H22N . . 109.5 ?
    C21E C22E H22O . . 109.5 ?
    H22M C22E H22O . . 109.5 ?
    H22N C22E H22O . . 109.5 ?
    C13E O11E H11G . . 109.5 ?
    C2E O21E C21E . . 117.6 ?
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C6A C1A C2A O21A . . . . -179.7(2) ?
    C11A C1A C2A O21A . . . . -1.0(3) ?
    C6A C1A C2A C3A . . . . 1.7(4) ?
    C11A C1A C2A C3A . . . . -179.5(2) ?
    O21A C2A C3A C4A . . . . -179.7(2) ?
    C1A C2A C3A C4A . . . . -1.3(4) ?
    C2A C3A C4A C5A . . . . 0.6(4) ?
    C3A C4A C5A C6A . . . . -0.4(4) ?
    C4A C5A C6A C1A . . . . 0.8(4) ?
    C2A C1A C6A C5A . . . . -1.5(4) ?
    C11A C1A C6A C5A . . . . 179.8(2) ?
    C6A C1A C11A C12A . . . . 1.0(4) ?
    C2A C1A C11A C12A . . . . -177.8(2) ?
    C1A C11A C12A C13A . . . . 179.3(2) ?
    C11A C12A C13A O11A . . . . 179.4(2) ?
    C11A C12A C13A O12A . . . . -1.2(4) ?
    C3A C2A O21A C21A . . . . 0.1(4) ?
    C1A C2A O21A C21A . . . . -178.4(2) ?
    C22A C21A O21A C2A . . . . 175.7(2) ?
    C6B C1B C2B O21B . . . . 179.6(2) ?
    C11B C1B C2B O21B . . . . 0.8(3) ?
    C6B C1B C2B C3B . . . . -0.4(3) ?
    C11B C1B C2B C3B . . . . -179.2(2) ?
    O21B C2B C3B C4B . . . . 179.9(2) ?
    C1B C2B C3B C4B . . . . -0.1(4) ?
    C2B C3B C4B C5B . . . . 0.5(4) ?
    C3B C4B C5B C6B . . . . -0.3(4) ?
    C4B C5B C6B C1B . . . . -0.2(4) ?
    C2B C1B C6B C5B . . . . 0.6(4) ?
    C11B C1B C6B C5B . . . . 179.3(2) ?
    C6B C1B C11B C12B . . . . 8.5(4) ?
    C2B C1B C11B C12B . . . . -172.8(2) ?
    C1B C11B C12B C13B . . . . -179.6(2) ?
    C11B C12B C13B O12B . . . . 6.0(4) ?
    C11B C12B C13B O11B . . . . -174.2(2) ?
    C3B C2B O21B C21B . . . . -1.8(3) ?
    C1B C2B O21B C21B . . . . 178.21(19) ?
    C22B C21B O21B C2B . . . . -176.56(19) ?
    C6C C1C C2C O21C . . . . -179.96(19) ?
    C11C C1C C2C O21C . . . . -1.2(3) ?
    C6C C1C C2C C3C . . . . -0.4(3) ?
    C11C C1C C2C C3C . . . . 178.4(2) ?
    O21C C2C C3C C4C . . . . 179.3(2) ?
    C1C C2C C3C C4C . . . . -0.3(3) ?
    C2C C3C C4C C5C . . . . 0.7(4) ?
    C3C C4C C5C C6C . . . . -0.5(4) ?
    C4C C5C C6C C1C . . . . -0.2(4) ?
    C2C C1C C6C C5C . . . . 0.6(3) ?
    C11C C1C C6C C5C . . . . -178.1(2) ?
    C6C C1C C11C C12C . . . . 1.7(3) ?
    C2C C1C C11C C12C . . . . -176.9(2) ?
    C1C C11C C12C C13C . . . . 178.88(19) ?
    C11C C12C C13C O12C . . . . 4.9(3) ?
    C11C C12C C13C O11C . . . . -175.92(19) ?
    C3C C2C O21C C21C . . . . -3.0(3) ?
    C1C C2C O21C C21C . . . . 176.63(17) ?
    C22C C21C O21C C2C . . . . -174.50(18) ?
    C6D C1D C2D O21D . . . . 179.8 ?
    C11D C1D C2D O21D . . . . 8.7 ?
    C6D C1D C2D C3D . . . . -1.6 ?
    C11D C1D C2D C3D . . . . -172.7 ?
    O21D C2D C3D C4D . . . . -179.8 ?
    C1D C2D C3D C4D . . . . 1.7 ?
    C2D C3D C4D C5D . . . . -1.5 ?
    C3D C4D C5D C6D . . . . 1.1 ?
    C4D C5D C6D C1D . . . . -1.0 ?
    C2D C1D C6D C5D . . . . 1.3 ?
    C11D C1D C6D C5D . . . . 171.5 ?
    C2D C1D C11D C12D . . . . -176.6 ?
    C6D C1D C11D C12D . . . . 13.1 ?
    C2D C1D C11D C12E . . . . 77.8 ?
    C6D C1D C11D C12E . . . . -92.6 ?
    C1D C11D C12D C13D . . . . 125.2 ?
    C12E C11D C12D C13D . . . . -114.3 ?
    C1D C11D C12D C11E . . . . -119.8 ?
    C12E C11D C12D C11E . . . . 0.7 ?
    C11D C12D C13D O12D . . . . 31.8 ?
    C11E C12D C13D O12D . . . . -69.5 ?
    C11D C12D C13D O11D . . . . -157.0 ?
    C11E C12D C13D O11D . . . . 101.6 ?
    C1D C2D O21D C21D . . . . -169.1 ?
    C3D C2D O21D C21D . . . . 12.3 ?
    C22D C21D O21D C2D . . . . 174.3 ?
    C6E C1E C2E O21E . . . . 179.2 ?
    C11E C1E C2E O21E . . . . -11.3 ?
    C6E C1E C2E C3E . . . . 0.2 ?
    C11E C1E C2E C3E . . . . 169.8 ?
    C1E C2E C3E C4E . . . . 0.1 ?
    O21E C2E C3E C4E . . . . -178.7 ?
    C2E C3E C4E C5E . . . . 0.0 ?
    C3E C4E C5E C6E . . . . -0.5 ?
    C4E C5E C6E C1E . . . . 0.9 ?
    C2E C1E C6E C5E . . . . -0.7 ?
    C11E C1E C6E C5E . . . . -169.2 ?
    C2E C1E C11E C12E . . . . -176.1 ?
    C6E C1E C11E C12E . . . . -7.4 ?
    C2E C1E C11E C12D . . . . -69.7 ?
    C6E C1E C11E C12D . . . . 99.1 ?
    C13D C12D C11E C1E . . . . -7.3 ?
    C11D C12D C11E C1E . . . . -124.2 ?
    C13D C12D C11E C12E . . . . 116.2 ?
    C11D C12D C11E C12E . . . . -0.7 ?
    C1E C11E C12E C13E . . . . -123.6 ?
    C12D C11E C12E C13E . . . . 115.4 ?
    C1E C11E C12E C11D . . . . 121.7 ?
    C12D C11E C12E C11D . . . . 0.7 ?
    C1D C11D C12E C13E . . . . 4.5 ?
    C12D C11D C12E C13E . . . . -118.3 ?
    C1D C11D C12E C11E . . . . 122.1 ?
    C12D C11D C12E C11E . . . . -0.7 ?
    C11E C12E C13E O12E . . . . -23.8 ?
    C11D C12E C13E O12E . . . . 77.5 ?
    C11E C12E C13E O11E . . . . 165.0 ?
    C11D C12E C13E O11E . . . . -93.7 ?
    C1E C2E O21E C21E . . . . 165.9 ?
    C3E C2E O21E C21E . . . . -15.2 ?
    C22E C21E O21E C2E . . . . -171.1 ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    O12A H1A O11A 2_655 0.84 1.73 2.566(3) 170.4
    O11B H1B O12C 2_766 0.84 1.76 2.591(2) 167.7
    O11C H1C O12B 2_766 0.84 1.80 2.622(3) 166.0
