##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and 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 is obtainable 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/  #
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#                                                                            #
#            Copyright International Union of Crystallography                #
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##############################################################################
                                             
data_global
_audit_creation_method     'from SHELXL97 CIF, local template and enCIFer'
_journal_date_recd_electronic     2004-01-22
_journal_date_accepted     2004-01-27
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2004
_journal_volume     60
_journal_issue      3
_journal_page_first     o331
_journal_page_last     o333
_journal_paper_category     EO
_publ_contact_author_name     'Dr Jeffrey R. Deschamps'
_publ_contact_author_address
;
Laboratory for the Structure of Matter
Naval Research Laboratory
Washington, DC 20375
;
_publ_contact_author_email     deschamps@nrl.navy.mil
_publ_contact_author_fax     '202-767-6874'
_publ_contact_author_phone     '202-767-0656'
_publ_section_title
;
7β,14β-Epoxyhydrocodone-6,6-dimethoxy ketal: an unusual
oxetane-containing opioid
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Deschamps, Jeffrey R.' ?
;
Laboratory for the Structure of Matter, Code 6030
Naval Research Laboratory
Washington, DC 20375, USA
;
    'Coop, Andrew'
;
Current address: Department of Pharmaceutical Sciences
University of Maryland School of Pharmacy
20 North Pine Street
Baltimore, MD 21201, USA
;
;
Laboratory of Medicinal Chemistry
Building 8, Room B1-23
National Institute of Diabetes and Digestive and Kidney Diseases
National Institutes of Health
8 Center Drive MSC 0815
Bethesda, MD 20892, USA
;
    'Parrish, Damon A.' ?
;
Laboratory for the Structure of Matter, Code 6030
Naval Research Laboratory
Washington, DC 20375, USA
;
    'Rice, Kenner C.' ?
;
Laboratory of Medicinal Chemistry
Building 8, Room B1-23
National Institute of Diabetes and Digestive and Kidney Diseases
National Institutes of Health
8 Center Drive MSC 0815
Bethesda, MD 20892, USA
;
data_4
_audit_creation_method     SHELXL
_chemical_name_systematic
;
;
_chemical_name_common     ?
_chemical_formula_moiety     'C20 H25 N O5'
_chemical_formula_sum     'C20 H25 N O5'
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_iupac     'C20 H25 N O5'
_chemical_formula_weight     359.41
_chemical_melting_point     ?
_symmetry_cell_setting     'triclinic'
_symmetry_space_group_name_H-M     'P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
_cell_length_a     7.509(2)
_cell_length_b     7.777(2)
_cell_length_c     8.430(2)
_cell_angle_alpha     83.776(6)
_cell_angle_beta     68.993(5)
_cell_angle_gamma     71.511(5)
_cell_volume     435.81(19)
_cell_formula_units_Z     1
_cell_measurement_reflns_used     3226
_cell_measurement_theta_min     2.59
_cell_measurement_theta_max     28.30
_cell_measurement_temperature     103.0(10)
_exptl_crystal_description     'irregular prism'
_exptl_crystal_colour     'colorless'
_exptl_crystal_size_max     0.40
_exptl_crystal_size_mid     0.30
_exptl_crystal_size_min     0.25
_exptl_crystal_density_diffrn     1.369
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     192
_exptl_absorpt_coefficient_mu     0.098
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     '(SADABS; Bruker, 2000)'
_exptl_absorpt_correction_T_min     0.962
_exptl_absorpt_correction_T_max     0.976
_exptl_special_details
;
;
_diffrn_ambient_temperature     103.0(10)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device     'Bruker SMART 1000 CCD'
_diffrn_measurement_method     ω
_diffrn_reflns_number     3770
_diffrn_reflns_av_R_equivalents     0.0098
_diffrn_reflns_av_sigmaI/netI     0.0198
_diffrn_reflns_theta_min     2.59
_diffrn_reflns_theta_max     28.36
_diffrn_reflns_theta_full     28.36
_diffrn_measured_fraction_theta_max     0.945
_diffrn_measured_fraction_theta_full     0.945
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -10
_diffrn_reflns_limit_k_max     10
_diffrn_reflns_limit_l_min     -11
_diffrn_reflns_limit_l_max     11
_diffrn_standards_number     450
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     'variable'
_diffrn_standards_decay_%     '0.7'
_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     2063
_reflns_number_gt     2036
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0321
_refine_ls_R_factor_gt     0.0318
_refine_ls_wR_factor_gt     0.0832
_refine_ls_wR_factor_ref     0.0835
_refine_ls_goodness_of_fit_ref     1.030
_refine_ls_restrained_S_all     1.029
_refine_ls_number_reflns     2063
_refine_ls_number_parameters     239
_refine_ls_number_restraints     3
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
     'calc w = 1/[σ²(Fo²)+(0.0566P)²+0.0944P] 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     0.337
_refine_diff_density_min     -0.190
_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' 0.0181 0.0091
                         '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'
    'N' 'N' 0.0311 0.0180
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0492 0.0322
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'SMART (Bruker, 2001)'
_computing_cell_refinement     'SMART and SAINT (Bruker, 2002)'
_computing_data_reduction     'SAINT and XPREP (Bruker, 2001)'
_computing_structure_solution     'SHELXTL (Bruker, 2000)'
_computing_structure_refinement     'SHELXTL'
_computing_molecular_graphics     'SHELXTL'
_computing_publication_material     'SHELXTL'
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
    C1 0.2152(3) 0.4085(3) 0.5092(2) 0.0221(4) Uani d . 1 . . C
    H1A 0.2670 0.4890 0.4255 0.027 Uiso calc R 1 . . H
    C2 0.3019(3) 0.2216(3) 0.4836(2) 0.0224(4) Uani d . 1 . . C
    H2A 0.4036 0.1777 0.3783 0.027 Uiso calc R 1 . . H
    C3 0.2429(3) 0.0972(3) 0.6088(2) 0.0189(3) Uani d . 1 . . C
    O3A 0.3297(2) -0.08633(19) 0.60108(18) 0.0238(3) Uani d . 1 . . O
    C3A 0.4927(3) -0.1581(3) 0.4483(3) 0.0305(5) Uani d . 1 . . C
    H3AA 0.5357 -0.2908 0.4535 0.046 Uiso calc R 1 . . H
    H3AB 0.6045 -0.1129 0.4370 0.046 Uiso calc R 1 . . H
    H3AC 0.4491 -0.1196 0.3501 0.046 Uiso calc R 1 . . H
    C4 0.0850(2) 0.1698(2) 0.7569(2) 0.0159(3) Uani d . 1 . . C
    O3 0.03019(19) 0.07758(17) 0.90728(16) 0.0170(3) Uani d . 1 . . O
    C5 -0.1221(2) 0.2095(2) 1.0358(2) 0.0143(3) Uani d . 1 . . C
    H5A -0.2468 0.1720 1.0772 0.017 Uiso calc R 1 . . H
    C6 -0.0625(3) 0.2214(2) 1.1934(2) 0.0156(3) Uani d . 1 . . C
    O6A 0.1121(2) 0.08793(18) 1.19864(17) 0.0204(3) Uani d . 1 . . O
    C6A 0.0975(3) -0.0932(3) 1.2269(3) 0.0263(4) Uani d . 1 . . C
    H6AA 0.2318 -0.1798 1.1995 0.039 Uiso calc R 1 . . H
    H6AB 0.0312 -0.1170 1.1541 0.039 Uiso calc R 1 . . H
    H6AC 0.0194 -0.1065 1.3463 0.039 Uiso calc R 1 . . H
    O6B -0.23515(19) 0.20892(18) 1.33069(16) 0.0193(3) Uani d . 1 . . O
    C6B -0.2444(3) 0.2531(3) 1.4944(2) 0.0256(4) Uani d . 1 . . C
    H6BA -0.3537 0.2180 1.5825 0.038 Uiso calc R 1 . . H
    H6BB -0.2683 0.3839 1.5016 0.038 Uiso calc R 1 . . H
    H6BC -0.1176 0.1876 1.5113 0.038 Uiso calc R 1 . . H
    C7 -0.0219(3) 0.4024(2) 1.1979(2) 0.0174(3) Uani d . 1 . . C
    H7A 0.0263 0.4129 1.2916 0.021 Uiso calc R 1 . . H
    O7 -0.19684(19) 0.55205(17) 1.19093(16) 0.0182(3) Uani d . 1 . . O
    C8 0.1023(3) 0.4544(2) 1.0224(2) 0.0170(3) Uani d . 1 . . C
    H8A 0.1914 0.3509 0.9451 0.020 Uiso calc R 1 . . H
    H8B 0.1718 0.5430 1.0236 0.020 Uiso calc R 1 . . H
    C9 -0.1515(3) 0.7110(2) 0.9043(2) 0.0174(3) Uani d . 1 . . C
    H9A -0.1143 0.8047 0.9472 0.021 Uiso calc R 1 . . H
    C10 -0.0212(3) 0.6765(2) 0.7115(2) 0.0210(4) Uani d . 1 . . C
    H10A -0.1013 0.7486 0.6425 0.025 Uiso calc R 1 . . H
    H10B 0.0957 0.7211 0.6870 0.025 Uiso calc R 1 . . H
    C11 0.0537(3) 0.4791(2) 0.6558(2) 0.0179(3) Uani d . 1 . . C
    C12 -0.0173(3) 0.3519(2) 0.7694(2) 0.0152(3) Uani d . 1 . . C
    C13 -0.1669(2) 0.3951(2) 0.9449(2) 0.0134(3) Uani d . 1 . . C
    C14 -0.1057(2) 0.5382(2) 1.0055(2) 0.0154(3) Uani d . 1 . . C
    C15 -0.3874(3) 0.4662(2) 0.9584(2) 0.0168(3) Uani d . 1 . . C
    H15A -0.4186 0.3779 0.9044 0.020 Uiso calc R 1 . . H
    H15B -0.4731 0.4772 1.0798 0.020 Uiso calc R 1 . . H
    C16 -0.4350(3) 0.6492(2) 0.8736(2) 0.0193(3) Uani d . 1 . . C
    H16A -0.3657 0.6357 0.7491 0.023 Uiso calc R 1 . . H
    H16B -0.5807 0.6973 0.8960 0.023 Uiso calc R 1 . . H
    N17 -0.3696(2) 0.7754(2) 0.9403(2) 0.0194(3) Uani d . 1 . . N
    C17 -0.4354(3) 0.9591(3) 0.8775(3) 0.0268(4) Uani d . 1 . . C
    H17C -0.5818 1.0015 0.9155 0.040 Uiso calc R 1 . . H
    H17D -0.3809 0.9584 0.7530 0.040 Uiso calc R 1 . . H
    H17A -0.3875 1.0404 0.9219 0.040 Uiso calc R 1 . . H
_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
    C1 C2 . 1.396(3) ?
    C1 C11 . 1.396(2) ?
    C1 H1A . 0.9500 ?
    C2 C3 . 1.401(3) ?
    C2 H2A . 0.9500 ?
    C3 O3A . 1.366(2) ?
    C3 C4 . 1.397(2) ?
    O3A C3A . 1.436(2) ?
    C3A H3AA . 0.9800 ?
    C3A H3AB . 0.9800 ?
    C3A H3AC . 0.9800 ?
    C4 C12 . 1.375(2) ?
    C4 O3 . 1.381(2) ?
    O3 C5 . 1.464(2) ?
    C5 C13 . 1.555(2) ?
    C5 C6 . 1.566(2) ?
    C5 H5A . 1.0000 ?
    C6 O6A . 1.403(2) ?
    C6 O6B . 1.417(2) ?
    C6 C7 . 1.539(2) ?
    O6A C6A . 1.435(2) ?
    C6A H6AA . 0.9800 ?
    C6A H6AB . 0.9800 ?
    C6A H6AC . 0.9800 ?
    O6B C6B . 1.431(2) ?
    C6B H6BA . 0.9800 ?
    C6B H6BB . 0.9800 ?
    C6B H6BC . 0.9800 ?
    C7 O7 . 1.468(2) ?
    C7 C8 . 1.530(2) ?
    C7 C14 . 2.020(3) ?
    C7 H7A . 1.0000 ?
    O7 C14 . 1.465(2) ?
    C8 C14 . 1.542(2) ?
    C8 H8A . 0.9900 ?
    C8 H8B . 0.9900 ?
    C9 N17 . 1.477(2) ?
    C9 C14 . 1.523(2) ?
    C9 C10 . 1.568(3) ?
    C9 H9A . 1.0000 ?
    C10 C11 . 1.520(3) ?
    C10 H10A . 0.9900 ?
    C10 H10B . 0.9900 ?
    C11 C12 . 1.394(2) ?
    C12 C13 . 1.497(2) ?
    C13 C14 . 1.526(2) ?
    C13 C15 . 1.535(2) ?
    C15 C16 . 1.518(2) ?
    C15 H15A . 0.9900 ?
    C15 H15B . 0.9900 ?
    C16 N17 . 1.464(2) ?
    C16 H16A . 0.9900 ?
    C16 H16B . 0.9900 ?
    N17 C17 . 1.463(2) ?
    C17 H17C . 0.9800 ?
    C17 H17D . 0.9800 ?
    C17 H17A . 0.9800 ?
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
    C2 C1 C11 . . 121.10(17) ?
    C2 C1 H1A . . 119.5 ?
    C11 C1 H1A . . 119.4 ?
    C1 C2 C3 . . 121.83(17) ?
    C1 C2 H2A . . 119.1 ?
    C3 C2 H2A . . 119.1 ?
    O3A C3 C4 . . 117.60(16) ?
    O3A C3 C2 . . 126.01(16) ?
    C4 C3 C2 . . 116.35(17) ?
    C3 O3A C3A . . 116.75(16) ?
    O3A C3A H3AA . . 109.5 ?
    O3A C3A H3AB . . 109.5 ?
    H3AA C3A H3AB . . 109.5 ?
    O3A C3A H3AC . . 109.5 ?
    H3AA C3A H3AC . . 109.5 ?
    H3AB C3A H3AC . . 109.5 ?
    C12 C4 O3 . . 113.41(15) ?
    C12 C4 C3 . . 120.72(16) ?
    O3 C4 C3 . . 125.48(16) ?
    C4 O3 C5 . . 107.61(13) ?
    O3 C5 C13 . . 107.11(13) ?
    O3 C5 C6 . . 113.73(14) ?
    C13 C5 C6 . . 112.29(13) ?
    O3 C5 H5A . . 107.8 ?
    C13 C5 H5A . . 107.8 ?
    C6 C5 H5A . . 107.8 ?
    O6A C6 O6B . . 112.74(14) ?
    O6A C6 C7 . . 104.74(14) ?
    O6B C6 C7 . . 111.25(14) ?
    O6A C6 C5 . . 114.87(14) ?
    O6B C6 C5 . . 102.05(13) ?
    C7 C6 C5 . . 111.41(14) ?
    C6 O6A C6A . . 115.15(15) ?
    O6A C6A H6AA . . 109.5 ?
    O6A C6A H6AB . . 109.5 ?
    H6AA C6A H6AB . . 109.5 ?
    O6A C6A H6AC . . 109.5 ?
    H6AA C6A H6AC . . 109.5 ?
    H6AB C6A H6AC . . 109.5 ?
    C6 O6B C6B . . 115.53(14) ?
    O6B C6B H6BA . . 109.5 ?
    O6B C6B H6BB . . 109.5 ?
    H6BA C6B H6BB . . 109.5 ?
    O6B C6B H6BC . . 109.5 ?
    H6BA C6B H6BC . . 109.5 ?
    H6BB C6B H6BC . . 109.5 ?
    O7 C7 C8 . . 90.10(13) ?
    O7 C7 C6 . . 108.95(14) ?
    C8 C7 C6 . . 111.94(14) ?
    O7 C7 C14 . . 46.41(8) ?
    C8 C7 C14 . . 49.14(10) ?
    C6 C7 C14 . . 101.61(12) ?
    O7 C7 H7A . . 114.5 ?
    C8 C7 H7A . . 114.5 ?
    C6 C7 H7A . . 114.5 ?
    C14 C7 H7A . . 143.8 ?
    C14 O7 C7 . . 87.06(12) ?
    C7 C8 C14 . . 82.22(13) ?
    C7 C8 H8A . . 114.9 ?
    C14 C8 H8A . . 114.9 ?
    C7 C8 H8B . . 114.9 ?
    C14 C8 H8B . . 114.9 ?
    H8A C8 H8B . . 112.0 ?
    N17 C9 C14 . . 107.77(14) ?
    N17 C9 C10 . . 114.81(15) ?
    C14 C9 C10 . . 110.23(14) ?
    N17 C9 H9A . . 107.9 ?
    C14 C9 H9A . . 107.9 ?
    C10 C9 H9A . . 107.9 ?
    C11 C10 C9 . . 114.60(15) ?
    C11 C10 H10A . . 108.6 ?
    C9 C10 H10A . . 108.6 ?
    C11 C10 H10B . . 108.6 ?
    C9 C10 H10B . . 108.6 ?
    H10A C10 H10B . . 107.6 ?
    C12 C11 C1 . . 115.77(17) ?
    C12 C11 C10 . . 118.96(16) ?
    C1 C11 C10 . . 124.31(17) ?
    C4 C12 C11 . . 122.76(16) ?
    C4 C12 C13 . . 109.56(15) ?
    C11 C12 C13 . . 124.65(16) ?
    C12 C13 C14 . . 102.68(13) ?
    C12 C13 C15 . . 116.06(14) ?
    C14 C13 C15 . . 110.78(14) ?
    C12 C13 C5 . . 102.08(14) ?
    C14 C13 C5 . . 113.60(14) ?
    C15 C13 C5 . . 111.23(13) ?
    O7 C14 C9 . . 117.29(14) ?
    O7 C14 C13 . . 108.38(13) ?
    C9 C14 C13 . . 108.65(13) ?
    O7 C14 C8 . . 89.75(13) ?
    C9 C14 C8 . . 121.07(14) ?
    C13 C14 C8 . . 110.20(14) ?
    O7 C14 C7 . . 46.53(9) ?
    C9 C14 C7 . . 151.15(13) ?
    C13 C14 C7 . . 99.90(12) ?
    C8 C14 C7 . . 48.64(9) ?
    C16 C15 C13 . . 111.98(14) ?
    C16 C15 H15A . . 109.2 ?
    C13 C15 H15A . . 109.2 ?
    C16 C15 H15B . . 109.2 ?
    C13 C15 H15B . . 109.2 ?
    H15A C15 H15B . . 107.9 ?
    N17 C16 C15 . . 109.50(15) ?
    N17 C16 H16A . . 109.8 ?
    C15 C16 H16A . . 109.8 ?
    N17 C16 H16B . . 109.8 ?
    C15 C16 H16B . . 109.8 ?
    H16A C16 H16B . . 108.2 ?
    C17 N17 C16 . . 111.02(16) ?
    C17 N17 C9 . . 112.28(15) ?
    C16 N17 C9 . . 111.34(14) ?
    N17 C17 H17C . . 109.5 ?
    N17 C17 H17D . . 109.5 ?
    H17C C17 H17D . . 109.5 ?
    N17 C17 H17A . . 109.5 ?
    H17C C17 H17A . . 109.5 ?
    H17D C17 H17A . . 109.5 ?
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
    C11 C1 C2 C3 . . . . -5.5(3) ?
    C1 C2 C3 O3A . . . . -174.20(18) ?
    C1 C2 C3 C4 . . . . 3.5(3) ?
    C4 C3 O3A C3A . . . . -179.55(17) ?
    C2 C3 O3A C3A . . . . -1.8(3) ?
    O3A C3 C4 C12 . . . . -175.97(16) ?
    C2 C3 C4 C12 . . . . 6.1(3) ?
    O3A C3 C4 O3 . . . . 11.6(3) ?
    C2 C3 C4 O3 . . . . -166.28(16) ?
    C12 C4 O3 C5 . . . . -0.92(19) ?
    C3 C4 O3 C5 . . . . 171.95(16) ?
    C4 O3 C5 C13 . . . . 3.60(17) ?
    C4 O3 C5 C6 . . . . -121.07(15) ?
    O3 C5 C6 O6A . . . . -8.5(2) ?
    C13 C5 C6 O6A . . . . -130.38(15) ?
    O3 C5 C6 O6B . . . . -130.85(14) ?
    C13 C5 C6 O6B . . . . 107.30(15) ?
    O3 C5 C6 C7 . . . . 110.34(16) ?
    C13 C5 C6 C7 . . . . -11.50(18) ?
    O6B C6 O6A C6A . . . . 48.0(2) ?
    C7 C6 O6A C6A . . . . 169.14(14) ?
    C5 C6 O6A C6A . . . . -68.31(19) ?
    O6A C6 O6B C6B . . . . 68.66(19) ?
    C7 C6 O6B C6B . . . . -48.7(2) ?
    C5 C6 O6B C6B . . . . -167.58(15) ?
    O6A C6 C7 O7 . . . . 179.38(13) ?
    O6B C6 C7 O7 . . . . -58.53(18) ?
    C5 C6 C7 O7 . . . . 54.62(17) ?
    O6A C6 C7 C8 . . . . 81.32(17) ?
    O6B C6 C7 C8 . . . . -156.59(14) ?
    C5 C6 C7 C8 . . . . -43.44(19) ?
    O6A C6 C7 C14 . . . . 131.73(12) ?
    O6B C6 C7 C14 . . . . -106.18(14) ?
    C5 C6 C7 C14 . . . . 6.97(16) ?
    C8 C7 O7 C14 . . . . 25.20(12) ?
    C6 C7 O7 C14 . . . . -88.11(14) ?
    O7 C7 C8 C14 . . . . -24.06(12) ?
    C6 C7 C8 C14 . . . . 86.47(15) ?
    N17 C9 C10 C11 . . . . -99.08(18) ?
    C14 C9 C10 C11 . . . . 22.8(2) ?
    C2 C1 C11 C12 . . . . -2.1(3) ?
    C2 C1 C11 C10 . . . . 166.60(18) ?
    C9 C10 C11 C12 . . . . 8.1(2) ?
    C9 C10 C11 C1 . . . . -160.26(17) ?
    O3 C4 C12 C11 . . . . 158.83(16) ?
    C3 C4 C12 C11 . . . . -14.4(3) ?
    O3 C4 C12 C13 . . . . -2.3(2) ?
    C3 C4 C12 C13 . . . . -175.55(15) ?
    C1 C11 C12 C4 . . . . 12.0(3) ?
    C10 C11 C12 C4 . . . . -157.32(17) ?
    C1 C11 C12 C13 . . . . 170.23(17) ?
    C10 C11 C12 C13 . . . . 0.9(3) ?
    C4 C12 C13 C14 . . . . 122.12(15) ?
    C11 C12 C13 C14 . . . . -38.6(2) ?
    C4 C12 C13 C15 . . . . -116.90(17) ?
    C11 C12 C13 C15 . . . . 82.4(2) ?
    C4 C12 C13 C5 . . . . 4.22(18) ?
    C11 C12 C13 C5 . . . . -156.48(17) ?
    O3 C5 C13 C12 . . . . -4.67(17) ?
    C6 C5 C13 C12 . . . . 120.87(15) ?
    O3 C5 C13 C14 . . . . -114.46(15) ?
    C6 C5 C13 C14 . . . . 11.09(19) ?
    O3 C5 C13 C15 . . . . 119.74(15) ?
    C6 C5 C13 C15 . . . . -114.72(15) ?
    C7 O7 C14 C9 . . . . -150.33(15) ?
    C7 O7 C14 C13 . . . . 86.26(14) ?
    C7 O7 C14 C8 . . . . -24.99(12) ?
    N17 C9 C14 O7 . . . . -61.14(18) ?
    C10 C9 C14 O7 . . . . 172.87(14) ?
    N17 C9 C14 C13 . . . . 62.13(17) ?
    C10 C9 C14 C13 . . . . -63.86(18) ?
    N17 C9 C14 C8 . . . . -168.91(15) ?
    C10 C9 C14 C8 . . . . 65.1(2) ?
    N17 C9 C14 C7 . . . . -109.2(3) ?
    C10 C9 C14 C7 . . . . 124.8(3) ?
    C12 C13 C14 O7 . . . . -162.52(14) ?
    C15 C13 C14 O7 . . . . 72.94(16) ?
    C5 C13 C14 O7 . . . . -53.10(17) ?
    C12 C13 C14 C9 . . . . 69.01(17) ?
    C15 C13 C14 C9 . . . . -55.52(17) ?
    C5 C13 C14 C9 . . . . 178.43(13) ?
    C12 C13 C14 C8 . . . . -65.78(16) ?
    C15 C13 C14 C8 . . . . 169.68(13) ?
    C5 C13 C14 C8 . . . . 43.64(18) ?
    C12 C13 C14 C7 . . . . -115.21(13) ?
    C15 C13 C14 C7 . . . . 120.26(13) ?
    C5 C13 C14 C7 . . . . -5.79(16) ?
    C7 C8 C14 O7 . . . . 24.11(12) ?
    C7 C8 C14 C9 . . . . 146.30(16) ?
    C7 C8 C14 C13 . . . . -85.43(15) ?
    C8 C7 C14 O7 . . . . -145.74(17) ?
    C6 C7 C14 O7 . . . . 105.19(14) ?
    O7 C7 C14 C9 . . . . 65.7(3) ?
    C8 C7 C14 C9 . . . . -80.0(3) ?
    C6 C7 C14 C9 . . . . 170.9(3) ?
    O7 C7 C14 C13 . . . . -105.99(14) ?
    C8 C7 C14 C13 . . . . 108.26(15) ?
    C6 C7 C14 C13 . . . . -0.80(15) ?
    O7 C7 C14 C8 . . . . 145.74(17) ?
    C6 C7 C14 C8 . . . . -109.07(16) ?
    C12 C13 C15 C16 . . . . -65.1(2) ?
    C14 C13 C15 C16 . . . . 51.43(19) ?
    C5 C13 C15 C16 . . . . 178.79(14) ?
    C13 C15 C16 N17 . . . . -53.0(2) ?
    C15 C16 N17 C17 . . . . -172.87(15) ?
    C15 C16 N17 C9 . . . . 61.24(19) ?
    C14 C9 N17 C17 . . . . 168.38(15) ?
    C10 C9 N17 C17 . . . . -68.4(2) ?
    C14 C9 N17 C16 . . . . -66.43(18) ?
    C10 C9 N17 C16 . . . . 56.8(2) ?
