#------------------------------------------------------------------------------
#$Date: 2021-07-05 20:03:55 +0300 (Mon, 05 Jul 2021) $
#$Revision: 267098 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/29/7242971.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7242971
loop_
_publ_author_name
'Niu, Yuan-Yuan'
'Wang, Ling-Yang'
'Yu, Yue-Ming'
'Li, Yan-Tuan'
'Wu, Zhi-Yong'
'Yan, Cui-Wei'
_publ_section_title
;
 Molecular adduct of amantadine ferulate presents a pathway for slowing in
 vitro/vivo releases and raising synergistic antiviral effects via dual
 optimization salification strategy
;
_journal_issue                   24
_journal_name_full               CrystEngComm
_journal_page_first              4389
_journal_page_last               4401
_journal_paper_doi               10.1039/D1CE00382H
_journal_volume                  23
_journal_year                    2021
_chemical_formula_moiety         '(C10 H18 N +), (C10 H9 O4 -), 0.5(C3 H8 O)'
_chemical_formula_sum            'C21.5 H31 N O4.5'
_chemical_formula_weight         375.47
_chemical_melting_point          215.0
_chemical_name_common            'Amantadine ferulate isopropanol solvate'
_chemical_name_systematic
'1-Adamantylammonium 3-(4-Hydroxy-3-methoxyphenyl)-2-propenoic acid propan-2-ol'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2016/4
_audit_update_record
;
2021-01-06 deposited with the CCDC.	2021-05-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.122(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.7505(4)
_cell_length_b                   10.1320(4)
_cell_length_c                   18.7022(8)
_cell_measurement_reflns_used    3833
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      73.2000
_cell_measurement_theta_min      4.3520
_cell_volume                     1983.93(14)
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  Bruker
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            7925
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.175
_diffrn_reflns_theta_min         4.367
_exptl_absorpt_coefficient_mu    0.704
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_description       block
_exptl_crystal_F_000             812
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Isopropanol/ethanol'
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     376
_refine_ls_number_reflns         3871
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0456
_refine_ls_R_factor_gt           0.0396
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0544P)²+0.5240P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1001
_refine_ls_wR_factor_ref         0.1058
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3367
_reflns_number_total             3871
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ce00382h2.cif
_cod_data_source_block           shelx
_cod_depositor_comments          'Adding full bibliography for 7242971.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_original_formula_sum        'C21.50 H31 N O4.50'
_cod_database_code               7242971
_shelx_shelxl_version_number     2016/4
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.844
_shelx_estimated_absorpt_t_max   0.872
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.39613(12) 0.74710(11) 0.25342(6) 0.0243(3) Uani 1 1 d . . . . .
C1 C 0.47593(11) 0.65257(12) 0.22143(6) 0.0176(3) Uani 1 1 d . . . . .
C2 C 0.54154(12) 0.55530(13) 0.28023(7) 0.0216(3) Uani 1 1 d . . . . .
C3 C 0.62376(13) 0.46010(15) 0.24633(8) 0.0296(3) Uani 1 1 d . . . . .
C4 C 0.72442(13) 0.53902(18) 0.21765(8) 0.0327(3) Uani 1 1 d . . . . .
C5 C 0.65791(12) 0.63742(14) 0.15911(7) 0.0233(3) Uani 1 1 d . . . . .
C6 C 0.57622(13) 0.73209(13) 0.19309(7) 0.0244(3) Uani 1 1 d . . . . .
C7 C 0.38927(12) 0.57788(14) 0.15798(7) 0.0233(3) Uani 1 1 d . . . . .
C8 C 0.47194(13) 0.48348(14) 0.12391(7) 0.0257(3) Uani 1 1 d . . . . .
C9 C 0.57163(12) 0.56341(14) 0.09534(7) 0.0235(3) Uani 1 1 d . . . . .
C10 C 0.53865(16) 0.38568(14) 0.18239(9) 0.0336(3) Uani 1 1 d . . . . .
O1 O 0.21106(9) 0.61503(10) 0.30652(5) 0.0274(2) Uani 1 1 d . . . . .
O2 O 0.22265(11) 0.41557(11) 0.35887(6) 0.0377(3) Uani 1 1 d . . . . .
O3 O 0.41404(9) 1.12718(9) 0.59452(5) 0.0240(2) Uani 1 1 d . . . . .
O4 O 0.55509(9) 0.99816(10) 0.70156(5) 0.0279(2) Uani 1 1 d . . . . .
C11 C 0.24446(12) 0.53684(14) 0.36131(7) 0.0238(3) Uani 1 1 d . . . . .
C12 C 0.31288(12) 0.59379(13) 0.43267(7) 0.0224(3) Uani 1 1 d . . . . .
C13 C 0.31907(11) 0.72322(13) 0.44610(7) 0.0196(3) Uani 1 1 d . . . . .
C14 C 0.37912(11) 0.78895(12) 0.51506(6) 0.0178(3) Uani 1 1 d . . . . .
C15 C 0.36476(11) 0.92632(12) 0.52030(7) 0.0182(3) Uani 1 1 d . . . . .
C16 C 0.42253(11) 0.99382(12) 0.58335(7) 0.0182(3) Uani 1 1 d . . . . .
C17 C 0.49932(11) 0.92521(13) 0.64260(7) 0.0199(3) Uani 1 1 d . . . . .
C18 C 0.51386(12) 0.78948(13) 0.63767(7) 0.0214(3) Uani 1 1 d . . . . .
C19 C 0.45368(12) 0.72171(13) 0.57495(7) 0.0206(3) Uani 1 1 d . . . . .
C20 C 0.33112(13) 1.20056(13) 0.53752(8) 0.0276(3) Uani 1 1 d . . . . .
O5 O 0.1062(2) 0.3605(2) 0.47401(11) 0.0317(5) Uani 0.5 1 d . . P A -1
C21 C -0.0622(5) 0.5234(6) 0.4541(3) 0.0790(19) Uani 0.5 1 d . . P A -1
H21A H -0.045931 0.536740 0.405156 0.119 Uiso 0.5 1 calc R U P A -1
H21B H -0.086860 0.607472 0.472813 0.119 Uiso 0.5 1 calc R U P A -1
H21C H -0.131376 0.459216 0.451190 0.119 Uiso 0.5 1 calc R U P A -1
C22 C 0.0320(3) 0.4256(4) 0.57714(19) 0.0417(8) Uani 0.5 1 d D . P A -1
H22A H -0.028222 0.351541 0.568107 0.063 Uiso 0.5 1 calc R U P A -1
H22B H -0.004760 0.498074 0.600282 0.063 Uiso 0.5 1 calc R U P A -1
H22C H 0.112151 0.396891 0.609731 0.063 Uiso 0.5 1 calc R U P A -1
C23 C 0.0577(4) 0.4720(4) 0.5055(2) 0.0386(8) Uani 0.5 1 d D . P A -1
H23 H 0.123814 0.543181 0.515002 0.046 Uiso 0.5 1 calc R U P A -1
H5A H 0.134(4) 0.389(4) 0.433(2) 0.045(10) Uiso 0.5 1 d . . P B -1
H1A H 0.3339(17) 0.7008(18) 0.2734(10) 0.040(5) Uiso 1 1 d . . . . .
H7A H 0.3241(15) 0.5257(16) 0.1773(8) 0.027(4) Uiso 1 1 d . . . . .
H9A H 0.6260(16) 0.5034(17) 0.0718(9) 0.033(4) Uiso 1 1 d . . . . .
H13 H 0.2789(15) 0.7841(16) 0.4050(9) 0.030(4) Uiso 1 1 d . . . . .
H15 H 0.3135(15) 0.9751(16) 0.4787(8) 0.025(4) Uiso 1 1 d . . . . .
H18 H 0.5677(16) 0.7470(17) 0.6787(10) 0.034(4) Uiso 1 1 d . . . . .
H5 H 0.7239(15) 0.6890(17) 0.1408(9) 0.029(4) Uiso 1 1 d . . . . .
H6A H 0.5330(15) 0.7963(16) 0.1554(9) 0.027(4) Uiso 1 1 d . . . . .
H19 H 0.4674(14) 0.6267(16) 0.5716(8) 0.024(4) Uiso 1 1 d . . . . .
H4A H 0.7794(18) 0.480(2) 0.1966(10) 0.047(5) Uiso 1 1 d . . . . .
H10A H 0.4724(17) 0.3303(18) 0.1990(9) 0.038(5) Uiso 1 1 d . . . . .
H2A H 0.5952(16) 0.6042(16) 0.3234(9) 0.033(4) Uiso 1 1 d . . . . .
H7B H 0.3441(17) 0.6419(18) 0.1207(10) 0.036(4) Uiso 1 1 d . . . . .
H8 H 0.4154(16) 0.4343(18) 0.0825(9) 0.037(4) Uiso 1 1 d . . . . .
H6B H 0.6305(16) 0.7809(18) 0.2352(10) 0.038(5) Uiso 1 1 d . . . . .
H2B H 0.4749(15) 0.5077(16) 0.2994(9) 0.030(4) Uiso 1 1 d . . . . .
H3 H 0.6662(18) 0.3956(19) 0.2863(10) 0.046(5) Uiso 1 1 d . . . . .
H12 H 0.3494(16) 0.5291(17) 0.4692(9) 0.033(4) Uiso 1 1 d . . . . .
H20A H 0.3381(16) 1.2948(18) 0.5533(9) 0.038(5) Uiso 1 1 d . . . . .
H1B H 0.3505(18) 0.811(2) 0.2145(11) 0.049(5) Uiso 1 1 d . . . . .
H20B H 0.3606(16) 1.1946(17) 0.4894(10) 0.035(4) Uiso 1 1 d . . . . .
H9B H 0.5250(17) 0.6263(18) 0.0562(10) 0.039(5) Uiso 1 1 d . . . . .
H1C H 0.4476(18) 0.8027(19) 0.2910(10) 0.043(5) Uiso 1 1 d . . . . .
H10B H 0.5915(18) 0.324(2) 0.1584(10) 0.047(5) Uiso 1 1 d . . . . .
H4 H 0.612(2) 0.948(2) 0.7401(12) 0.067(7) Uiso 1 1 d . . . . .
H20C H 0.2404(16) 1.1682(17) 0.5300(9) 0.035(4) Uiso 1 1 d . . . . .
H4B H 0.7836(19) 0.587(2) 0.2587(11) 0.050(5) Uiso 1 1 d . . . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 H1A 110.9(11) . . ?
C1 N1 H1B 110.3(11) . . ?
H1A N1 H1B 108.9(15) . . ?
C1 N1 H1C 112.1(11) . . ?
H1A N1 H1C 109.6(15) . . ?
H1B N1 H1C 104.8(15) . . ?
N1 C1 C2 109.77(9) . . ?
N1 C1 C7 108.81(10) . . ?
C2 C1 C7 109.86(11) . . ?
N1 C1 C6 108.27(10) . . ?
C2 C1 C6 110.03(10) . . ?
C7 C1 C6 110.08(10) . . ?
C1 C2 C3 108.84(10) . . ?
C1 C2 H2A 110.3(9) . . ?
C3 C2 H2A 111.1(9) . . ?
C1 C2 H2B 108.6(9) . . ?
C3 C2 H2B 111.9(9) . . ?
H2A C2 H2B 106.1(13) . . ?
C10 C3 C4 109.10(11) . . ?
C10 C3 C2 109.48(11) . . ?
C4 C3 C2 109.48(12) . . ?
C10 C3 H3 110.2(11) . . ?
C4 C3 H3 110.9(10) . . ?
C2 C3 H3 107.7(10) . . ?
C5 C4 C3 109.67(11) . . ?
C5 C4 H4A 109.6(11) . . ?
C3 C4 H4A 111.0(11) . . ?
C5 C4 H4B 110.2(12) . . ?
C3 C4 H4B 111.0(11) . . ?
H4A C4 H4B 105.3(16) . . ?
C9 C5 C4 109.87(12) . . ?
C9 C5 C6 109.08(10) . . ?
C4 C5 C6 109.23(11) . . ?
C9 C5 H5 109.9(9) . . ?
C4 C5 H5 109.4(9) . . ?
C6 C5 H5 109.4(9) . . ?
C5 C6 C1 109.18(10) . . ?
C5 C6 H6A 109.6(9) . . ?
C1 C6 H6A 109.7(9) . . ?
C5 C6 H6B 110.5(10) . . ?
C1 C6 H6B 108.6(10) . . ?
H6A C6 H6B 109.3(14) . . ?
C1 C7 C8 108.72(10) . . ?
C1 C7 H7A 109.3(9) . . ?
C8 C7 H7A 109.6(9) . . ?
C1 C7 H7B 109.6(10) . . ?
C8 C7 H7B 110.6(10) . . ?
H7A C7 H7B 109.0(13) . . ?
C10 C8 C9 109.90(11) . . ?
C10 C8 C7 109.15(11) . . ?
C9 C8 C7 109.34(11) . . ?
C10 C8 H8 109.5(10) . . ?
C9 C8 H8 110.1(10) . . ?
C7 C8 H8 108.8(10) . . ?
C5 C9 C8 109.58(10) . . ?
C5 C9 H9A 109.0(10) . . ?
C8 C9 H9A 110.7(10) . . ?
C5 C9 H9B 111.6(10) . . ?
C8 C9 H9B 108.3(10) . . ?
H9A C9 H9B 107.7(13) . . ?
C8 C10 C3 109.89(11) . . ?
C8 C10 H10A 109.4(10) . . ?
C3 C10 H10A 111.9(10) . . ?
C8 C10 H10B 107.5(11) . . ?
C3 C10 H10B 110.7(11) . . ?
H10A C10 H10B 107.4(14) . . ?
C16 O3 C20 116.68(10) . . ?
C17 O4 H4 113.9(13) . . ?
O2 C11 O1 124.25(12) . . ?
O2 C11 C12 117.71(12) . . ?
O1 C11 C12 118.04(12) . . ?
C13 C12 C11 122.96(12) . . ?
C13 C12 H12 122.7(10) . . ?
C11 C12 H12 114.3(10) . . ?
C12 C13 C14 127.30(12) . . ?
C12 C13 H13 117.7(9) . . ?
C14 C13 H13 115.0(9) . . ?
C19 C14 C15 118.60(11) . . ?
C19 C14 C13 122.81(11) . . ?
C15 C14 C13 118.55(11) . . ?
C16 C15 C14 120.92(11) . . ?
C16 C15 H15 119.4(9) . . ?
C14 C15 H15 119.6(9) . . ?
O3 C16 C15 125.72(11) . . ?
O3 C16 C17 114.45(11) . . ?
C15 C16 C17 119.82(11) . . ?
O4 C17 C18 124.09(12) . . ?
O4 C17 C16 116.46(11) . . ?
C18 C17 C16 119.45(11) . . ?
C19 C18 C17 120.57(12) . . ?
C19 C18 H18 122.6(10) . . ?
C17 C18 H18 116.8(10) . . ?
C18 C19 C14 120.61(12) . . ?
C18 C19 H19 119.6(9) . . ?
C14 C19 H19 119.7(9) . . ?
O3 C20 H20A 106.5(10) . . ?
O3 C20 H20B 111.1(10) . . ?
H20A C20 H20B 107.4(14) . . ?
O3 C20 H20C 110.7(10) . . ?
H20A C20 H20C 111.0(14) . . ?
H20B C20 H20C 110.0(14) . . ?
C23 O5 H5A 108(2) . . ?
C23 C21 H21A 109.5 . . ?
C23 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C23 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 H22A 109.5 . . ?
C23 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C23 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O5 C23 C22 106.2(3) . . ?
O5 C23 C21 110.4(4) . . ?
C22 C23 C21 111.7(4) . . ?
O5 C23 H23 109.5 . . ?
C22 C23 H23 109.5 . . ?
C21 C23 H23 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.4981(15) . ?
N1 H1A 0.959(19) . ?
N1 H1B 1.01(2) . ?
N1 H1C 0.97(2) . ?
C1 C2 1.5250(17) . ?
C1 C7 1.5320(17) . ?
C1 C6 1.5336(17) . ?
C2 C3 1.5389(18) . ?
C2 H2A 1.009(17) . ?
C2 H2B 0.995(16) . ?
C3 C10 1.529(2) . ?
C3 C4 1.537(2) . ?
C3 H3 1.018(19) . ?
C4 C5 1.532(2) . ?
C4 H4A 0.984(19) . ?
C4 H4B 1.00(2) . ?
C5 C9 1.5306(18) . ?
C5 C6 1.5326(18) . ?
C5 H5 1.002(16) . ?
C6 H6A 0.993(16) . ?
C6 H6B 0.998(18) . ?
C7 C8 1.5388(18) . ?
C7 H7A 1.008(16) . ?
C7 H7B 0.994(18) . ?
C8 C10 1.528(2) . ?
C8 C9 1.5330(18) . ?
C8 H8 1.001(17) . ?
C9 H9A 1.011(17) . ?
C9 H9B 1.013(18) . ?
C10 H10A 1.010(18) . ?
C10 H10B 1.02(2) . ?
O1 C11 1.2804(17) . ?
O2 C11 1.2497(17) . ?
O3 C16 1.3734(15) . ?
O3 C20 1.4326(16) . ?
O4 C17 1.3495(15) . ?
O4 H4 0.98(2) . ?
C11 C12 1.4864(17) . ?
C12 C13 1.3340(18) . ?
C12 H12 0.964(17) . ?
C13 C14 1.4648(17) . ?
C13 H13 1.004(17) . ?
C14 C19 1.3977(17) . ?
C14 C15 1.4063(17) . ?
C15 C16 1.3825(17) . ?
C15 H15 0.980(16) . ?
C16 C17 1.4061(17) . ?
C17 C18 1.3896(18) . ?
C18 C19 1.3860(18) . ?
C18 H18 0.952(17) . ?
C19 H19 0.978(16) . ?
C20 H20A 0.997(19) . ?
C20 H20B 1.021(17) . ?
C20 H20C 1.009(17) . ?
O5 C23 1.426(4) . ?
O5 H5A 0.93(4) . ?
C21 C23 1.514(6) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C23 1.504(4) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23 1.0000 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 -179.51(11) . . . . ?
C7 C1 C2 C3 60.88(13) . . . . ?
C6 C1 C2 C3 -60.47(14) . . . . ?
C1 C2 C3 C10 -59.75(14) . . . . ?
C1 C2 C3 C4 59.81(14) . . . . ?
C10 C3 C4 C5 59.82(16) . . . . ?
C2 C3 C4 C5 -59.97(15) . . . . ?
C3 C4 C5 C9 -59.65(15) . . . . ?
C3 C4 C5 C6 59.96(16) . . . . ?
C9 C5 C6 C1 60.13(14) . . . . ?
C4 C5 C6 C1 -59.97(14) . . . . ?
N1 C1 C6 C5 -179.22(10) . . . . ?
C2 C1 C6 C5 60.82(13) . . . . ?
C7 C1 C6 C5 -60.40(14) . . . . ?
N1 C1 C7 C8 178.54(10) . . . . ?
C2 C1 C7 C8 -61.27(13) . . . . ?
C6 C1 C7 C8 60.04(14) . . . . ?
C1 C7 C8 C10 60.29(14) . . . . ?
C1 C7 C8 C9 -59.95(14) . . . . ?
C4 C5 C9 C8 58.96(14) . . . . ?
C6 C5 C9 C8 -60.74(14) . . . . ?
C10 C8 C9 C5 -58.96(14) . . . . ?
C7 C8 C9 C5 60.83(14) . . . . ?
C9 C8 C10 C3 59.78(14) . . . . ?
C7 C8 C10 C3 -60.13(14) . . . . ?
C4 C3 C10 C8 -59.93(14) . . . . ?
C2 C3 C10 C8 59.86(14) . . . . ?
O2 C11 C12 C13 -166.17(13) . . . . ?
O1 C11 C12 C13 13.45(18) . . . . ?
C11 C12 C13 C14 177.28(11) . . . . ?
C12 C13 C14 C19 8.31(19) . . . . ?
C12 C13 C14 C15 -173.96(12) . . . . ?
C19 C14 C15 C16 -0.27(17) . . . . ?
C13 C14 C15 C16 -178.10(10) . . . . ?
C20 O3 C16 C15 4.40(17) . . . . ?
C20 O3 C16 C17 -176.55(10) . . . . ?
C14 C15 C16 O3 -179.46(11) . . . . ?
C14 C15 C16 C17 1.54(17) . . . . ?
O3 C16 C17 O4 -0.71(15) . . . . ?
C15 C16 C17 O4 178.40(10) . . . . ?
O3 C16 C17 C18 179.42(10) . . . . ?
C15 C16 C17 C18 -1.47(17) . . . . ?
O4 C17 C18 C19 -179.71(11) . . . . ?
C16 C17 C18 C19 0.15(18) . . . . ?
C17 C18 C19 C14 1.13(18) . . . . ?
C15 C14 C19 C18 -1.06(17) . . . . ?
C13 C14 C19 C18 176.67(11) . . . . ?
