data_2203342
loop_
_publ_author_name
'Deschamps, Jeffrey R.'
'Coop, Andrew'
'Parrish, Damon A.'
'Rice, Kenner C.'
_publ_section_title
;
7\b,14\b-Epoxyhydrocodone-6,6-dimethoxy ketal: an unusual
oxetane-containing opioid
;
_journal_issue                 3
_journal_name_full             'Acta Crystallographica, Section E'
_journal_page_first            o331
_journal_page_last             o333
_journal_volume                60
_journal_year                  2004
_chemical_formula_analytical   ?
_chemical_formula_iupac        'C20 H25 N O5'
_chemical_formula_moiety       'C20 H25 N O5'
_chemical_formula_structural   ?
_chemical_formula_sum          'C20 H25 N O5'
_chemical_formula_weight       359.41
_chemical_melting_point        ?
_chemical_name_common          ?
_chemical_name_systematic      
;
;
_symmetry_cell_setting         triclinic
_symmetry_space_group_name_H-M 'P 1'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary   direct
_atom_sites_solution_secondary difmap
_audit_creation_method         SHELXL
_cell_angle_alpha              83.776(6)
_cell_angle_beta               68.993(5)
_cell_angle_gamma              71.511(5)
_cell_formula_units_Z          1
_cell_length_a                 7.509(2)
_cell_length_b                 7.777(2)
_cell_length_c                 8.430(2)
_cell_measurement_reflns_used  3226
_cell_measurement_temperature  103.0(10)
_cell_measurement_theta_max    28.30
_cell_measurement_theta_min    2.59
_cell_volume                   435.81(19)
_computing_cell_refinement     'SMART and SAINT (Bruker, 2002)'
_computing_data_collection     'SMART (Bruker, 2001)'
_computing_data_reduction      'SAINT and XPREP (Bruker, 2001)'
_computing_molecular_graphics  SHELXTL
_computing_publication_material SHELXTL
_computing_structure_refinement SHELXTL
_computing_structure_solution  'SHELXTL (Bruker, 2000)'
_diffrn_ambient_temperature    103.0(10)
_diffrn_measured_fraction_theta_full 0.945
_diffrn_measured_fraction_theta_max 0.945
_diffrn_measurement_device     'Bruker SMART 1000 CCD'
_diffrn_measurement_method     \w
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source       'sealed tube'
_diffrn_radiation_type         MoK\a
_diffrn_radiation_wavelength   0.71073
_diffrn_reflns_av_R_equivalents 0.0098
_diffrn_reflns_av_sigmaI/netI  0.0198
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_k_max     10
_diffrn_reflns_limit_k_min     -10
_diffrn_reflns_limit_l_max     11
_diffrn_reflns_limit_l_min     -11
_diffrn_reflns_number          3770
_diffrn_reflns_theta_full      28.36
_diffrn_reflns_theta_max       28.36
_diffrn_reflns_theta_min       2.59
_diffrn_standards_decay_%      0.7
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time variable
_diffrn_standards_number       450
_exptl_absorpt_coefficient_mu  0.098
_exptl_absorpt_correction_T_max 0.976
_exptl_absorpt_correction_T_min 0.962
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details '(SADABS; Bruker, 2000)'
_exptl_crystal_colour          colorless
_exptl_crystal_density_diffrn  1.369
_exptl_crystal_density_meas    ?
_exptl_crystal_density_method  'not measured'
_exptl_crystal_description     'irregular prism'
_exptl_crystal_F_000           192
_exptl_crystal_size_max        0.40
_exptl_crystal_size_mid        0.30
_exptl_crystal_size_min        0.25
_refine_diff_density_max       0.337
_refine_diff_density_min       -0.190
_refine_ls_extinction_coef     ?
_refine_ls_extinction_method   none
_refine_ls_goodness_of_fit_ref 1.030
_refine_ls_hydrogen_treatment  constr
_refine_ls_matrix_type         full
_refine_ls_number_parameters   239
_refine_ls_number_reflns       2063
_refine_ls_number_restraints   3
_refine_ls_restrained_S_all    1.029
_refine_ls_R_factor_all        0.0321
_refine_ls_R_factor_gt         0.0318
_refine_ls_shift/su_max        0.000
_refine_ls_shift/su_mean       0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[\s^2^(Fo^2^)+(0.0566P)^2^+0.0944P] where P = (Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme    calc
_refine_ls_wR_factor_gt        0.0832
_refine_ls_wR_factor_ref       0.0835
_reflns_number_gt              2036
_reflns_number_total           2063
_reflns_threshold_expression   I>2\s(I)
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
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
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
C1 0.0201(8) 0.0300(10) 0.0154(8) -0.0095(8) -0.0042(7) 0.0028(7)
C2 0.0158(8) 0.0341(11) 0.0145(8) -0.0060(8) -0.0025(6) -0.0030(7)
C3 0.0149(8) 0.0236(9) 0.0176(8) -0.0039(7) -0.0051(6) -0.0052(7)
O3A 0.0185(6) 0.0237(7) 0.0222(7) -0.0004(5) -0.0016(5) -0.0091(5)
C3A 0.0213(9) 0.0349(11) 0.0253(10) 0.0022(8) -0.0018(8) -0.0136(8)
C4 0.0139(8) 0.0192(8) 0.0155(8) -0.0057(6) -0.0050(6) -0.0014(6)
O3 0.0183(6) 0.0145(6) 0.0144(6) -0.0020(5) -0.0027(5) -0.0031(5)
C5 0.0131(7) 0.0142(7) 0.0142(7) -0.0027(6) -0.0038(6) -0.0014(6)
C6 0.0147(8) 0.0162(8) 0.0144(7) -0.0028(6) -0.0044(6) -0.0009(6)
O6A 0.0183(6) 0.0195(6) 0.0237(6) -0.0019(5) -0.0105(5) -0.0008(5)
C6A 0.0305(10) 0.0188(9) 0.0286(10) -0.0021(8) -0.0143(8) 0.0025(7)
O6B 0.0191(6) 0.0253(7) 0.0128(6) -0.0077(5) -0.0036(5) 0.0000(5)
C6B 0.0279(10) 0.0335(11) 0.0147(8) -0.0087(8) -0.0065(7) -0.0013(7)
C7 0.0180(8) 0.0187(8) 0.0171(8) -0.0041(7) -0.0080(6) -0.0032(6)
O7 0.0191(6) 0.0176(6) 0.0163(6) -0.0023(5) -0.0061(5) -0.0035(5)
C8 0.0157(8) 0.0168(8) 0.0209(8) -0.0065(6) -0.0075(6) -0.0003(6)
C9 0.0175(8) 0.0135(8) 0.0225(9) -0.0052(6) -0.0080(7) 0.0004(6)
C10 0.0183(8) 0.0190(9) 0.0228(9) -0.0062(7) -0.0041(7) 0.0033(7)
C11 0.0145(8) 0.0223(9) 0.0170(8) -0.0060(7) -0.0054(6) 0.0017(7)
C12 0.0118(7) 0.0200(8) 0.0130(7) -0.0041(6) -0.0032(6) -0.0023(6)
C13 0.0122(7) 0.0134(8) 0.0142(7) -0.0038(6) -0.0038(6) -0.0009(6)
C14 0.0139(7) 0.0149(8) 0.0168(8) -0.0038(6) -0.0047(6) -0.0015(6)
C15 0.0126(7) 0.0178(8) 0.0196(8) -0.0044(6) -0.0048(6) -0.0005(6)
C16 0.0159(8) 0.0177(8) 0.0248(9) -0.0039(6) -0.0087(6) 0.0008(7)
N17 0.0163(7) 0.0143(7) 0.0274(8) -0.0029(6) -0.0084(6) -0.0005(6)
C17 0.0255(10) 0.0164(9) 0.0388(11) -0.0036(7) -0.0146(9) 0.0032(8)
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'
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_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_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) ?