#------------------------------------------------------------------------------
#$Date: 2025-08-19 00:06:14 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301780 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/92/1559277.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_1559277
loop_
_publ_author_name
'Ren, Shuyue'
'Jiao, Lingtai'
'Yang, Shiying'
'Zhang, Li'
'Song, Junke'
'Yu, Haoying'
'Wang, Jingrong'
'Lv, Tingting'
'Sun, Lan'
'Lu, Yang'
'Du, Guanhua'
_publ_section_title
;
 A Novel Co-Crystal of Bexarotene and Ligustrazine Improves
 Pharmacokinetics and Tissue Distribution of Bexarotene in SD Rats.
;
_journal_issue                   10
_journal_name_full               Pharmaceutics
_journal_page_first              906
_journal_paper_doi               10.3390/pharmaceutics12100906
_journal_volume                  12
_journal_year                    2020
_chemical_formula_moiety         'C24 H28 O2, C4 H6 N'
_chemical_formula_sum            'C28 H34 N O2'
_chemical_formula_weight         416.56
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2020-09-16
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 100.410(5)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   49.281(20)
_cell_length_b                   8.517(3)
_cell_length_c                   11.787(4)
_cell_measurement_reflns_used    67.679
_cell_measurement_temperature    566(2)
_cell_measurement_theta_max      72.897
_cell_measurement_theta_min      5.279
_cell_volume                     4866(3)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      566.3
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0710
_diffrn_reflns_av_unetI/netI     0.0525
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       54
_diffrn_reflns_limit_h_min       -60
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            17931
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.679
_diffrn_reflns_theta_min         5.273
_exptl_absorpt_coefficient_mu    0.546
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.137
_exptl_crystal_density_method    "'not measured'"
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1800
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.370
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.961
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     296
_refine_ls_number_reflns         4729
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.962
_refine_ls_R_factor_all          0.0804
_refine_ls_R_factor_gt           0.0621
_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)+(0.1065P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1693
_refine_ls_wR_factor_ref         0.1887
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2886
_reflns_number_total             4729
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            2BEX-LIG.cif
_cod_data_source_block           2BEX-LIG
_cod_database_code               1559277
_shelx_shelxl_version_number     2018/3
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Rigid bond restraints
 C2, C7
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C2, C1
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3.a Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C17(H17A,H17B)
3.b Aromatic/amide H refined with riding coordinates:
 C15(H15), C12(H12), C6(H6), C4(H4), C3(H3), C7(H7)
3.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C23(H23A,H23B,H23C), C24(H24A,H24B,
 H24C), C22(H22A,H22B,H22C), C28(H28A,H28B,H28C), C25(H25A,H25B,H25C)
3.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
C10 C 0.10768(3) 0.1147(2) 0.01276(13) 0.0450(4) Uani 1 1 d . . . . .
C15 C 0.08037(3) 0.1220(2) 0.02690(14) 0.0474(4) Uani 1 1 d . . . . .
H15 H 0.068932 0.037609 0.001034 0.057 Uiso 1 1 calc R . . . .
C13 C 0.08649(4) 0.3720(2) 0.11960(14) 0.0487(4) Uani 1 1 d . . . . .
C8 C 0.11713(3) -0.0218(2) -0.04900(14) 0.0490(4) Uani 1 1 d . . . . .
C12 C 0.11389(4) 0.3648(2) 0.10383(15) 0.0523(4) Uani 1 1 d . . . . .
H12 H 0.125385 0.448802 0.129870 0.063 Uiso 1 1 calc R . . . .
C11 C 0.12498(3) 0.2408(2) 0.05208(14) 0.0491(4) Uani 1 1 d . . . . .
C5 C 0.13945(3) -0.1242(2) 0.01060(15) 0.0495(4) Uani 1 1 d . . . . .
C14 C 0.06905(3) 0.2481(2) 0.07753(14) 0.0484(4) Uani 1 1 d . . . . .
O2 O 0.20857(4) -0.4231(2) 0.29023(15) 0.0944(6) Uani 1 1 d . . . . .
H2 H 0.220069 -0.489273 0.316786 0.142 Uiso 1 1 calc GR . . . .
C2 C 0.18131(4) -0.3231(3) 0.12191(19) 0.0609(5) Uani 1 1 d . U . . .
O1 O 0.21510(3) -0.5230(2) 0.12336(15) 0.0849(5) Uani 1 1 d . . . . .
C6 C 0.14681(4) -0.1245(3) 0.13076(16) 0.0604(5) Uani 1 1 d . . . . .
H6 H 0.137794 -0.058168 0.174443 0.073 Uiso 1 1 calc R . . . .
C4 C 0.15391(4) -0.2253(3) -0.05056(17) 0.0593(5) Uani 1 1 d . . . . .
H4 H 0.149633 -0.225798 -0.130710 0.071 Uiso 1 1 calc R . . . .
C3 C 0.17415(4) -0.3237(3) 0.00357(18) 0.0626(5) Uani 1 1 d . . . . .
H3 H 0.183077 -0.391139 -0.039751 0.075 Uiso 1 1 calc R . . . .
C7 C 0.16754(4) -0.2236(3) 0.18537(17) 0.0658(5) Uani 1 1 d . U . . .
H7 H 0.172224 -0.223102 0.265426 0.079 Uiso 1 1 calc R . . . .
C16 C 0.03830(4) 0.2432(3) 0.08445(18) 0.0633(5) Uani 1 1 d . . . . .
C19 C 0.07678(5) 0.5159(3) 0.17881(18) 0.0648(6) Uani 1 1 d . . . . .
C9 C 0.10425(5) -0.0518(3) -0.15647(18) 0.0673(6) Uani 1 1 d . . . . .
C20 C 0.15448(4) 0.2492(3) 0.0324(2) 0.0714(6) Uani 1 1 d . . . . .
H20A H 0.164844 0.163345 0.071368 0.107 Uiso 1 1 calc GR . . . .
H20B H 0.162603 0.346661 0.062047 0.107 Uiso 1 1 calc GR . . . .
H20C H 0.154683 0.242764 -0.048781 0.107 Uiso 1 1 calc GR . . . .
C1 C 0.20340(4) -0.4338(3) 0.1769(2) 0.0661(6) Uani 1 1 d . U . . .
C21 C 0.09683(7) 0.5554(4) 0.2902(2) 0.1021(10) Uani 1 1 d . . . . .
H21A H 0.098779 0.465925 0.340563 0.153 Uiso 1 1 calc GR . . . .
H21B H 0.089809 0.642560 0.327609 0.153 Uiso 1 1 calc GR . . . .
H21C H 0.114490 0.582289 0.272153 0.153 Uiso 1 1 calc GR . . . .
C23 C 0.02101(5) 0.2074(4) -0.0332(2) 0.0942(9) Uani 1 1 d . . . . .
H23A H 0.025207 0.282028 -0.088583 0.141 Uiso 1 1 calc GR . . . .
H23B H 0.001792 0.214178 -0.028717 0.141 Uiso 1 1 calc GR . . . .
H23C H 0.025137 0.103407 -0.056540 0.141 Uiso 1 1 calc GR . . . .
C18 C 0.04881(6) 0.4817(4) 0.2120(3) 0.0985(9) Uani 1 1 d . . . . .
H18A H 0.051657 0.415865 0.280342 0.118 Uiso 1 1 calc R . . . .
H18B H 0.040817 0.579798 0.231783 0.118 Uiso 1 1 calc R . . . .
C17 C 0.02919(5) 0.4040(4) 0.1216(3) 0.0938(9) Uani 1 1 d . . . . .
H17A H 0.025817 0.472038 0.054575 0.113 Uiso 1 1 calc R . . . .
H17B H 0.011841 0.391514 0.148567 0.113 Uiso 1 1 calc R . . . .
C24 C 0.03333(5) 0.1156(4) 0.1691(3) 0.0966(9) Uani 1 1 d . . . . .
H24A H 0.039434 0.016292 0.144457 0.145 Uiso 1 1 calc GR . . . .
H24B H 0.013992 0.110019 0.171670 0.145 Uiso 1 1 calc GR . . . .
H24C H 0.043431 0.140067 0.244533 0.145 Uiso 1 1 calc GR . . . .
C22 C 0.07553(7) 0.6574(3) 0.0984(3) 0.0964(9) Uani 1 1 d . . . . .
H22A H 0.093259 0.672968 0.077284 0.145 Uiso 1 1 calc GR . . . .
H22B H 0.070542 0.749274 0.137078 0.145 Uiso 1 1 calc GR . . . .
H22C H 0.061994 0.638777 0.030227 0.145 Uiso 1 1 calc GR . . . .
N1 N 0.24245(4) 0.3503(2) 0.40821(14) 0.0660(5) Uani 1 1 d . . . . .
C26 C 0.23286(4) 0.2021(3) 0.40411(17) 0.0635(6) Uani 1 1 d . . . . .
C27 C 0.25960(4) 0.3991(3) 0.50235(17) 0.0632(5) Uani 1 1 d . . . . .
C28 C 0.27026(6) 0.5632(3) 0.5042(2) 0.0898(8) Uani 1 1 d . . . . .
H28A H 0.289885 0.561270 0.508024 0.135 Uiso 1 1 calc GR . . . .
H28B H 0.266062 0.617226 0.570383 0.135 Uiso 1 1 calc GR . . . .
H28C H 0.261701 0.616830 0.435302 0.135 Uiso 1 1 calc GR . . . .
C25 C 0.21421(5) 0.1493(4) 0.2968(2) 0.0849(7) Uani 1 1 d . . . . .
H25A H 0.212932 0.230212 0.239368 0.127 Uiso 1 1 calc GR . . . .
H25B H 0.196205 0.128202 0.313475 0.127 Uiso 1 1 calc GR . . . .
H25C H 0.221509 0.055537 0.268524 0.127 Uiso 1 1 calc GR . . . .
H9A H 0.0898(4) 0.023(3) -0.1925(18) 0.065(6) Uiso 1 1 d . . . . .
H9B H 0.1086(5) -0.140(3) -0.201(2) 0.080(7) 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
C15 C10 C8 119.28(16) . . ?
C15 C10 C11 118.21(16) . . ?
C11 C10 C8 122.42(15) . . ?
C10 C15 H15 118.0 . . ?
C10 C15 C14 123.93(17) . . ?
C14 C15 H15 118.0 . . ?
C12 C13 C19 119.04(17) . . ?
C14 C13 C12 117.89(16) . . ?
C14 C13 C19 123.05(16) . . ?
C5 C8 C10 119.96(15) . . ?
C9 C8 C10 118.41(18) . . ?
C9 C8 C5 121.58(18) . . ?
C13 C12 H12 117.9 . . ?
C11 C12 C13 124.18(17) . . ?
C11 C12 H12 117.9 . . ?
C10 C11 C20 122.00(17) . . ?
C12 C11 C10 117.91(15) . . ?
C12 C11 C20 119.97(17) . . ?
C6 C5 C8 121.19(16) . . ?
C6 C5 C4 117.27(17) . . ?
C4 C5 C8 121.54(16) . . ?
C15 C14 C13 117.84(15) . . ?
C15 C14 C16 118.55(17) . . ?
C13 C14 C16 123.61(17) . . ?
C1 O2 H2 109.5 . . ?
C3 C2 C7 119.24(19) . . ?
C3 C2 C1 118.05(19) . . ?
C7 C2 C1 122.7(2) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 C5 120.35(19) . . ?
C7 C6 H6 119.8 . . ?
C5 C4 H4 118.9 . . ?
C3 C4 C5 122.21(18) . . ?
C3 C4 H4 118.9 . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.14(19) . . ?
C4 C3 H3 119.9 . . ?
C2 C7 C6 120.78(19) . . ?
C2 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C23 C16 C14 110.68(16) . . ?
C23 C16 C17 107.2(2) . . ?
C23 C16 C24 108.9(2) . . ?
C17 C16 C14 109.57(18) . . ?
C24 C16 C14 109.36(18) . . ?
C24 C16 C17 111.1(2) . . ?
C13 C19 C21 111.12(19) . . ?
C18 C19 C13 109.57(19) . . ?
C18 C19 C21 107.1(2) . . ?
C22 C19 C13 109.26(17) . . ?
C22 C19 C21 107.9(2) . . ?
C22 C19 C18 111.9(2) . . ?
C8 C9 H9A 117.8(13) . . ?
C8 C9 H9B 123.6(15) . . ?
H9A C9 H9B 118.6(19) . . ?
C11 C20 H20A 109.5 . . ?
C11 C20 H20B 109.5 . . ?
C11 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O2 C1 C2 112.8(2) . . ?
O1 C1 O2 123.7(2) . . ?
O1 C1 C2 123.5(2) . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C16 C23 H23A 109.5 . . ?
C16 C23 H23B 109.5 . . ?
C16 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C19 C18 H18A 108.7 . . ?
C19 C18 H18B 108.7 . . ?
H18A C18 H18B 107.6 . . ?
C17 C18 C19 114.1(2) . . ?
C17 C18 H18A 108.7 . . ?
C17 C18 H18B 108.7 . . ?
C16 C17 H17A 108.5 . . ?
C16 C17 H17B 108.5 . . ?
C18 C17 C16 115.1(2) . . ?
C18 C17 H17A 108.5 . . ?
C18 C17 H17B 108.5 . . ?
H17A C17 H17B 107.5 . . ?
C16 C24 H24A 109.5 . . ?
C16 C24 H24B 109.5 . . ?
C16 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C27 N1 C26 119.21(19) . . ?
N1 C26 C27 120.6(2) . 7_556 ?
N1 C26 C25 118.1(2) . . ?
C27 C26 C25 121.2(2) 7_556 . ?
N1 C27 C26 120.2(2) . 7_556 ?
N1 C27 C28 118.2(2) . . ?
C26 C27 C28 121.6(2) 7_556 . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C26 C25 H25A 109.5 . . ?
C26 C25 H25B 109.5 . . ?
C26 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 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
C10 C15 1.387(2) . ?
C10 C8 1.491(3) . ?
C10 C11 1.397(3) . ?
C15 H15 0.9300 . ?
C15 C14 1.393(3) . ?
C13 C12 1.397(3) . ?
C13 C14 1.394(3) . ?
C13 C19 1.530(3) . ?
C8 C5 1.478(3) . ?
C8 C9 1.335(3) . ?
C12 H12 0.9300 . ?
C12 C11 1.380(3) . ?
C11 C20 1.515(3) . ?
C5 C6 1.397(3) . ?
C5 C4 1.398(3) . ?
C14 C16 1.533(3) . ?
O2 H2 0.8200 . ?
O2 C1 1.317(3) . ?
C2 C3 1.376(3) . ?
C2 C7 1.387(3) . ?
C2 C1 1.496(3) . ?
O1 C1 1.200(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.390(3) . ?
C4 H4 0.9300 . ?
C4 C3 1.369(3) . ?
C3 H3 0.9300 . ?
C7 H7 0.9300 . ?
C16 C23 1.521(3) . ?
C16 C17 1.530(4) . ?
C16 C24 1.525(3) . ?
C19 C21 1.531(4) . ?
C19 C18 1.528(3) . ?
C19 C22 1.527(4) . ?
C9 H9A 0.99(2) . ?
C9 H9B 0.96(3) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C17 1.461(4) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
N1 C26 1.345(3) . ?
N1 C27 1.334(3) . ?
C26 C27 1.396(3) 7_556 ?
C26 C25 1.492(3) . ?
C27 C28 1.492(3) . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
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
C10 C15 C14 C13 -2.1(2) . . . . ?
C10 C15 C14 C16 178.16(17) . . . . ?
C10 C8 C5 C6 17.9(3) . . . . ?
C10 C8 C5 C4 -162.59(18) . . . . ?
C15 C10 C8 C5 -120.18(18) . . . . ?
C15 C10 C8 C9 57.2(2) . . . . ?
C15 C10 C11 C12 0.6(2) . . . . ?
C15 C10 C11 C20 -175.27(17) . . . . ?
C15 C14 C16 C23 -51.5(3) . . . . ?
C15 C14 C16 C17 -169.5(2) . . . . ?
C15 C14 C16 C24 68.5(2) . . . . ?
C13 C12 C11 C10 0.1(3) . . . . ?
C13 C12 C11 C20 176.12(17) . . . . ?
C13 C14 C16 C23 128.8(2) . . . . ?
C13 C14 C16 C17 10.8(3) . . . . ?
C13 C14 C16 C24 -111.2(2) . . . . ?
C13 C19 C18 C17 -44.6(3) . . . . ?
C8 C10 C15 C14 -176.35(16) . . . . ?
C8 C10 C11 C12 177.22(15) . . . . ?
C8 C10 C11 C20 1.3(3) . . . . ?
C8 C5 C6 C7 178.89(18) . . . . ?
C8 C5 C4 C3 -178.29(18) . . . . ?
C12 C13 C14 C15 2.7(2) . . . . ?
C12 C13 C14 C16 -177.54(17) . . . . ?
C12 C13 C19 C21 -48.5(3) . . . . ?
C12 C13 C19 C18 -166.7(2) . . . . ?
C12 C13 C19 C22 70.4(2) . . . . ?
C11 C10 C15 C14 0.3(2) . . . . ?
C11 C10 C8 C5 63.3(2) . . . . ?
C11 C10 C8 C9 -119.3(2) . . . . ?
C5 C6 C7 C2 0.2(3) . . . . ?
C5 C4 C3 C2 -1.4(3) . . . . ?
C14 C13 C12 C11 -1.8(3) . . . . ?
C14 C13 C19 C21 133.2(2) . . . . ?
C14 C13 C19 C18 15.0(3) . . . . ?
C14 C13 C19 C22 -107.9(2) . . . . ?
C14 C16 C17 C18 -40.8(3) . . . . ?
C6 C5 C4 C3 1.2(3) . . . . ?
C4 C5 C6 C7 -0.6(3) . . . . ?
C3 C2 C7 C6 -0.3(3) . . . . ?
C3 C2 C1 O2 180.0(2) . . . . ?
C3 C2 C1 O1 -0.2(3) . . . . ?
C7 C2 C3 C4 0.9(3) . . . . ?
C7 C2 C1 O2 -1.5(3) . . . . ?
C7 C2 C1 O1 178.3(2) . . . . ?
C19 C13 C12 C11 179.73(17) . . . . ?
C19 C13 C14 C15 -178.96(16) . . . . ?
C19 C13 C14 C16 0.8(3) . . . . ?
C19 C18 C17 C16 61.0(4) . . . . ?
C9 C8 C5 C6 -159.4(2) . . . . ?
C9 C8 C5 C4 20.1(3) . . . . ?
C1 C2 C3 C4 179.53(18) . . . . ?
C1 C2 C7 C6 -178.89(19) . . . . ?
C21 C19 C18 C17 -165.3(3) . . . . ?
C23 C16 C17 C18 -160.9(3) . . . . ?
C24 C16 C17 C18 80.2(3) . . . . ?
C22 C19 C18 C17 76.7(3) . . . . ?
C26 N1 C27 C26 -0.9(3) . . . 7_556 ?
C26 N1 C27 C28 179.2(2) . . . . ?
C27 N1 C26 C27 0.9(3) . . . 7_556 ?
C27 N1 C26 C25 -178.63(18) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168306815
