#------------------------------------------------------------------------------
#$Date: 2025-08-19 15:18:28 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301805 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/68/2226814.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2226814
loop_
_publ_author_name
'Aridoss, G.'
'Sundaramoorthy, S.'
'Velmurugan, D.'
'Park, K. S.'
'Jeong, Y. T.'
_publ_section_title
;
 Ethyl
 4-hydroxy-2,6-diphenyl-1-[2-(piperidin-1-yl)acetyl]-1,2,5,6-tetrahydropyridine-3-carboxylate
;
_journal_coeditor_code           CI5118
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2005
_journal_paper_doi               10.1107/S1600536810026619
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C27 H32 N2 O4'
_chemical_formula_moiety         'C27 H32 N2 O4'
_chemical_formula_sum            'C27 H32 N2 O4'
_chemical_formula_weight         448.55
_chemical_name_systematic
;
Ethyl 4-hydroxy-2,6-diphenyl-1-[2-(piperidin-1-yl)acetyl]-1,2,5,6-
tetrahydropyridine-3-carboxylate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 93.213(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.7936(6)
_cell_length_b                   9.6752(6)
_cell_length_c                   23.2335(13)
_cell_measurement_reflns_used    1525
_cell_measurement_temperature    292(2)
_cell_measurement_theta_max      28.31
_cell_measurement_theta_min      1.76
_cell_volume                     2422.5(2)
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      292(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type
'Bruker SMART APEXII area-detector diffractometer'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_sigmaI/netI    0.0268
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            21907
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.31
_diffrn_reflns_theta_min         1.76
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_correction_T_min  0.979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.583
_refine_diff_density_min         -0.367
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         5870
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0945
_refine_ls_R_factor_gt           0.0576
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0946P)²+0.5359P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1646
_refine_ls_wR_factor_ref         0.1925
_reflns_number_gt                3631
_reflns_number_total             5870
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci5118.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2226814
_cod_database_fobs_code          2226814
loop_
_symmetry_equiv_pos_as_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_type_symbol
_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
C C27 0.3740(4) -0.0409(8) 0.2481(2) 0.206(3) Uani d D 1 . .
H H27A 0.4323 -0.0751 0.2218 0.308 Uiso calc R 1 . .
H H27B 0.3930 -0.0787 0.2857 0.308 Uiso calc R 1 . .
H H27C 0.3791 0.0581 0.2498 0.308 Uiso calc R 1 . .
C C1 0.08942(18) 0.31589(19) 0.01812(8) 0.0470(4) Uani d . 1 . .
H H1 0.0592 0.3326 -0.0218 0.056 Uiso calc R 1 . .
C C2 -0.02445(18) 0.2987(2) 0.05340(9) 0.0539(5) Uani d . 1 . .
H H2A -0.0605 0.3888 0.0600 0.065 Uiso calc R 1 . .
H H2B -0.0859 0.2436 0.0317 0.065 Uiso calc R 1 . .
C C3 0.00608(18) 0.2312(2) 0.10962(9) 0.0528(5) Uani d . 1 . .
C C4 0.10915(17) 0.1540(2) 0.12035(8) 0.0492(5) Uani d . 1 . .
C C5 0.20372(17) 0.1306(2) 0.07547(8) 0.0455(4) Uani d . 1 . .
H H5 0.2104 0.0302 0.0711 0.055 Uiso calc R 1 . .
C C6 0.33462(17) 0.1815(2) 0.09306(8) 0.0467(4) Uani d . 1 . .
C C7 0.35769(19) 0.2807(3) 0.13484(9) 0.0573(5) Uani d . 1 . .
H H7 0.2915 0.3222 0.1521 0.069 Uiso calc R 1 . .
C C8 0.4785(2) 0.3197(3) 0.15163(11) 0.0733(7) Uani d . 1 . .
H H8 0.4926 0.3864 0.1801 0.088 Uiso calc R 1 . .
C C9 0.5763(2) 0.2598(3) 0.12621(13) 0.0821(8) Uani d . 1 . .
H H9 0.6571 0.2854 0.1374 0.098 Uiso calc R 1 . .
C C10 0.5550(2) 0.1619(3) 0.08418(14) 0.0822(8) Uani d . 1 . .
H H10 0.6215 0.1217 0.0667 0.099 Uiso calc R 1 . .
C C11 0.4350(2) 0.1225(3) 0.06762(11) 0.0645(6) Uani d . 1 . .
H H11 0.4215 0.0557 0.0392 0.077 Uiso calc R 1 . .
C C12 0.17351(17) 0.4373(2) 0.03603(8) 0.0462(4) Uani d . 1 . .
C C13 0.1481(2) 0.5271(2) 0.08002(10) 0.0580(5) Uani d . 1 . .
H H13 0.0799 0.5107 0.1018 0.070 Uiso calc R 1 . .
C C14 0.2225(2) 0.6412(3) 0.09232(12) 0.0725(7) Uani d . 1 . .
H H14 0.2044 0.7001 0.1223 0.087 Uiso calc R 1 . .
C C15 0.3227(3) 0.6673(3) 0.06033(13) 0.0771(7) Uani d . 1 . .
H H15 0.3720 0.7446 0.0682 0.093 Uiso calc R 1 . .
C C16 0.3502(2) 0.5787(3) 0.01649(13) 0.0734(7) Uani d . 1 . .
H H16 0.4186 0.5956 -0.0051 0.088 Uiso calc R 1 . .
C C17 0.2763(2) 0.4647(2) 0.00461(10) 0.0591(5) Uani d . 1 . .
H H17 0.2957 0.4052 -0.0250 0.071 Uiso calc R 1 . .
C C18 0.15252(19) 0.0927(2) -0.02602(9) 0.0522(5) Uani d . 1 . .
C C19 0.0955(2) 0.1375(2) -0.08475(9) 0.0581(5) Uani d . 1 . .
H H19A 0.0885 0.0571 -0.1097 0.070 Uiso calc R 1 . .
H H19B 0.0122 0.1714 -0.0798 0.070 Uiso calc R 1 . .
C C20 0.2914(2) 0.1989(3) -0.12236(11) 0.0752(7) Uani d . 1 . .
H H20A 0.2891 0.1152 -0.1454 0.090 Uiso calc R 1 . .
H H20B 0.3334 0.1777 -0.0854 0.090 Uiso calc R 1 . .
C C21 0.3637(3) 0.3090(4) -0.15246(13) 0.0973(10) Uani d . 1 . .
H H21A 0.3713 0.3905 -0.1282 0.117 Uiso calc R 1 . .
H H21B 0.4466 0.2752 -0.1585 0.117 Uiso calc R 1 . .
C C22 0.2998(3) 0.3470(4) -0.20973(12) 0.0988(10) Uani d . 1 . .
H H22A 0.3428 0.4237 -0.2267 0.119 Uiso calc R 1 . .
H H22B 0.3018 0.2690 -0.2359 0.119 Uiso calc R 1 . .
C C23 0.1672(3) 0.3868(4) -0.20086(12) 0.0906(9) Uani d . 1 . .
H H23A 0.1240 0.4028 -0.2380 0.109 Uiso calc R 1 . .
H H23B 0.1658 0.4722 -0.1790 0.109 Uiso calc R 1 . .
C C24 0.1010(2) 0.2751(3) -0.16913(10) 0.0691(6) Uani d . 1 . .
H H24A 0.0169 0.3049 -0.1631 0.083 Uiso calc R 1 . .
H H24B 0.0964 0.1920 -0.1925 0.083 Uiso calc R 1 . .
C C25 0.1255(2) 0.0802(3) 0.17438(9) 0.0638(6) Uani d . 1 . .
C C26 0.2522(3) -0.0805(4) 0.22867(13) 0.1089(12) Uani d D 1 . .
H H26A 0.1940 -0.0565 0.2574 0.131 Uiso calc R 1 . .
H H26B 0.2487 -0.1797 0.2226 0.131 Uiso calc R 1 . .
N N1 0.15713(15) 0.18363(16) 0.01878(6) 0.0461(4) Uani d . 1 . .
N N2 0.16459(16) 0.24368(19) -0.11332(7) 0.0543(4) Uani d . 1 . .
O O1 0.19378(17) -0.02442(17) -0.02074(7) 0.0726(5) Uani d . 1 . .
O O2 -0.08101(14) 0.2495(2) 0.14807(7) 0.0731(5) Uani d . 1 . .
H H2 -0.0613 0.2069 0.1777 0.110 Uiso calc R 1 . .
O O3 0.05991(18) 0.0935(3) 0.21512(7) 0.0941(7) Uani d . 1 . .
O O4 0.21980(15) -0.0091(2) 0.17514(7) 0.0785(5) Uani d . 1 . .
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'
N N 0.0061 0.0033 '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'
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
C26 C27 H27A . . 109.5 ?
C26 C27 H27B . . 109.5 ?
H27A C27 H27B . . 109.5 ?
C26 C27 H27C . . 109.5 ?
H27A C27 H27C . . 109.5 ?
H27B C27 H27C . . 109.5 ?
N1 C1 C2 . . 108.30(16) ?
N1 C1 C12 . . 112.21(15) ?
C2 C1 C12 . . 114.98(17) ?
N1 C1 H1 . . 107.0 ?
C2 C1 H1 . . 107.0 ?
C12 C1 H1 . . 107.0 ?
C3 C2 C1 . . 112.11(16) ?
C3 C2 H2A . . 109.2 ?
C1 C2 H2A . . 109.2 ?
C3 C2 H2B . . 109.2 ?
C1 C2 H2B . . 109.2 ?
H2A C2 H2B . . 107.9 ?
O2 C3 C4 . . 123.3(2) ?
O2 C3 C2 . . 113.52(18) ?
C4 C3 C2 . . 123.13(18) ?
C3 C4 C25 . . 119.49(19) ?
C3 C4 C5 . . 122.28(17) ?
C25 C4 C5 . . 117.99(18) ?
N1 C5 C4 . . 110.69(15) ?
N1 C5 C6 . . 112.96(15) ?
C4 C5 C6 . . 114.55(16) ?
N1 C5 H5 . . 106.0 ?
C4 C5 H5 . . 106.0 ?
C6 C5 H5 . . 106.0 ?
C7 C6 C11 . . 118.2(2) ?
C7 C6 C5 . . 122.69(17) ?
C11 C6 C5 . . 119.04(19) ?
C6 C7 C8 . . 121.1(2) ?
C6 C7 H7 . . 119.5 ?
C8 C7 H7 . . 119.5 ?
C9 C8 C7 . . 119.8(3) ?
C9 C8 H8 . . 120.1 ?
C7 C8 H8 . . 120.1 ?
C8 C9 C10 . . 119.9(2) ?
C8 C9 H9 . . 120.1 ?
C10 C9 H9 . . 120.1 ?
C9 C10 C11 . . 120.4(2) ?
C9 C10 H10 . . 119.8 ?
C11 C10 H10 . . 119.8 ?
C10 C11 C6 . . 120.6(2) ?
C10 C11 H11 . . 119.7 ?
C6 C11 H11 . . 119.7 ?
C13 C12 C17 . . 117.8(2) ?
C13 C12 C1 . . 123.09(18) ?
C17 C12 C1 . . 118.96(18) ?
C12 C13 C14 . . 121.2(2) ?
C12 C13 H13 . . 119.4 ?
C14 C13 H13 . . 119.4 ?
C15 C14 C13 . . 120.1(2) ?
C15 C14 H14 . . 120.0 ?
C13 C14 H14 . . 120.0 ?
C14 C15 C16 . . 119.8(2) ?
C14 C15 H15 . . 120.1 ?
C16 C15 H15 . . 120.1 ?
C15 C16 C17 . . 120.0(2) ?
C15 C16 H16 . . 120.0 ?
C17 C16 H16 . . 120.0 ?
C16 C17 C12 . . 121.2(2) ?
C16 C17 H17 . . 119.4 ?
C12 C17 H17 . . 119.4 ?
O1 C18 N1 . . 121.68(19) ?
O1 C18 C19 . . 118.64(19) ?
N1 C18 C19 . . 119.68(18) ?
N2 C19 C18 . . 114.65(17) ?
N2 C19 H19A . . 108.6 ?
C18 C19 H19A . . 108.6 ?
N2 C19 H19B . . 108.6 ?
C18 C19 H19B . . 108.6 ?
H19A C19 H19B . . 107.6 ?
N2 C20 C21 . . 111.6(2) ?
N2 C20 H20A . . 109.3 ?
C21 C20 H20A . . 109.3 ?
N2 C20 H20B . . 109.3 ?
C21 C20 H20B . . 109.3 ?
H20A C20 H20B . . 108.0 ?
C22 C21 C20 . . 110.9(3) ?
C22 C21 H21A . . 109.5 ?
C20 C21 H21A . . 109.5 ?
C22 C21 H21B . . 109.5 ?
C20 C21 H21B . . 109.5 ?
H21A C21 H21B . . 108.0 ?
C23 C22 C21 . . 109.4(2) ?
C23 C22 H22A . . 109.8 ?
C21 C22 H22A . . 109.8 ?
C23 C22 H22B . . 109.8 ?
C21 C22 H22B . . 109.8 ?
H22A C22 H22B . . 108.2 ?
C22 C23 C24 . . 111.3(3) ?
C22 C23 H23A . . 109.4 ?
C24 C23 H23A . . 109.4 ?
C22 C23 H23B . . 109.4 ?
C24 C23 H23B . . 109.4 ?
H23A C23 H23B . . 108.0 ?
N2 C24 C23 . . 111.7(2) ?
N2 C24 H24A . . 109.3 ?
C23 C24 H24A . . 109.3 ?
N2 C24 H24B . . 109.3 ?
C23 C24 H24B . . 109.3 ?
H24A C24 H24B . . 107.9 ?
O3 C25 O4 . . 122.2(2) ?
O3 C25 C4 . . 125.0(2) ?
O4 C25 C4 . . 112.78(19) ?
C27 C26 O4 . . 108.6(3) ?
C27 C26 H26A . . 110.0 ?
O4 C26 H26A . . 110.0 ?
C27 C26 H26B . . 110.0 ?
O4 C26 H26B . . 110.0 ?
H26A C26 H26B . . 108.4 ?
C18 N1 C1 . . 123.80(16) ?
C18 N1 C5 . . 117.01(16) ?
C1 N1 C5 . . 117.08(14) ?
C19 N2 C20 . . 111.43(19) ?
C19 N2 C24 . . 108.92(17) ?
C20 N2 C24 . . 109.31(17) ?
C3 O2 H2 . . 109.5 ?
C25 O4 C26 . . 117.9(2) ?
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
C27 C26 . 1.418(4) ?
C27 H27A . 0.96 ?
C27 H27B . 0.96 ?
C27 H27C . 0.96 ?
C1 N1 . 1.473(2) ?
C1 C2 . 1.524(3) ?
C1 C12 . 1.528(3) ?
C1 H1 . 0.98 ?
C2 C3 . 1.481(3) ?
C2 H2A . 0.97 ?
C2 H2B . 0.97 ?
C3 O2 . 1.344(2) ?
C3 C4 . 1.352(3) ?
C4 C25 . 1.446(3) ?
C4 C5 . 1.516(3) ?
C5 N1 . 1.475(2) ?
C5 C6 . 1.530(3) ?
C5 H5 . 0.98 ?
C6 C7 . 1.378(3) ?
C6 C11 . 1.386(3) ?
C7 C8 . 1.392(3) ?
C7 H7 . 0.93 ?
C8 C9 . 1.367(4) ?
C8 H8 . 0.93 ?
C9 C10 . 1.371(4) ?
C9 H9 . 0.93 ?
C10 C11 . 1.384(4) ?
C10 H10 . 0.93 ?
C11 H11 . 0.93 ?
C12 C13 . 1.381(3) ?
C12 C17 . 1.388(3) ?
C13 C14 . 1.385(3) ?
C13 H13 . 0.93 ?
C14 C15 . 1.369(4) ?
C14 H14 . 0.93 ?
C15 C16 . 1.376(4) ?
C15 H15 . 0.93 ?
C16 C17 . 1.379(3) ?
C16 H16 . 0.93 ?
C17 H17 . 0.93 ?
C18 O1 . 1.221(3) ?
C18 N1 . 1.361(3) ?
C18 C19 . 1.528(3) ?
C19 N2 . 1.452(3) ?
C19 H19A . 0.97 ?
C19 H19B . 0.97 ?
C20 N2 . 1.463(3) ?
C20 C21 . 1.514(4) ?
C20 H20A . 0.97 ?
C20 H20B . 0.97 ?
C21 C22 . 1.509(4) ?
C21 H21A . 0.97 ?
C21 H21B . 0.97 ?
C22 C23 . 1.508(4) ?
C22 H22A . 0.97 ?
C22 H22B . 0.97 ?
C23 C24 . 1.510(4) ?
C23 H23A . 0.97 ?
C23 H23B . 0.97 ?
C24 N2 . 1.465(3) ?
C24 H24A . 0.97 ?
C24 H24B . 0.97 ?
C25 O3 . 1.220(3) ?
C25 O4 . 1.335(3) ?
C26 O4 . 1.448(3) ?
C26 H26A . 0.97 ?
C26 H26B . 0.97 ?
O2 H2 . 0.82 ?
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
O2 H2 O3 . 0.82 1.88 2.598(3) 145
C2 H2B O1 3 0.97 2.43 3.286(3) 148
C10 H10 O1 3_655 0.93 2.50 3.427(3) 177
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
N1 C1 C2 C3 . . . . 47.4(2) ?
C12 C1 C2 C3 . . . . -79.0(2) ?
C1 C2 C3 O2 . . . . 161.99(18) ?
C1 C2 C3 C4 . . . . -20.6(3) ?
O2 C3 C4 C25 . . . . 3.4(3) ?
C2 C3 C4 C25 . . . . -173.7(2) ?
O2 C3 C4 C5 . . . . 177.68(19) ?
C2 C3 C4 C5 . . . . 0.6(3) ?
C3 C4 C5 N1 . . . . -8.9(3) ?
C25 C4 C5 N1 . . . . 165.46(18) ?
C3 C4 C5 C6 . . . . 120.3(2) ?
C25 C4 C5 C6 . . . . -65.4(2) ?
N1 C5 C6 C7 . . . . 106.2(2) ?
C4 C5 C6 C7 . . . . -21.8(3) ?
N1 C5 C6 C11 . . . . -76.2(2) ?
C4 C5 C6 C11 . . . . 155.77(19) ?
C11 C6 C7 C8 . . . . -0.7(3) ?
C5 C6 C7 C8 . . . . 176.9(2) ?
C6 C7 C8 C9 . . . . 0.4(4) ?
C7 C8 C9 C10 . . . . 0.2(4) ?
C8 C9 C10 C11 . . . . -0.5(4) ?
C9 C10 C11 C6 . . . . 0.2(4) ?
C7 C6 C11 C10 . . . . 0.4(3) ?
C5 C6 C11 C10 . . . . -177.3(2) ?
N1 C1 C12 C13 . . . . -125.6(2) ?
C2 C1 C12 C13 . . . . -1.2(3) ?
N1 C1 C12 C17 . . . . 58.6(2) ?
C2 C1 C12 C17 . . . . -177.07(17) ?
C17 C12 C13 C14 . . . . 0.2(3) ?
C1 C12 C13 C14 . . . . -175.7(2) ?
C12 C13 C14 C15 . . . . 0.6(4) ?
C13 C14 C15 C16 . . . . -0.9(4) ?
C14 C15 C16 C17 . . . . 0.5(4) ?
C15 C16 C17 C12 . . . . 0.2(4) ?
C13 C12 C17 C16 . . . . -0.6(3) ?
C1 C12 C17 C16 . . . . 175.4(2) ?
O1 C18 C19 N2 . . . . -112.8(2) ?
N1 C18 C19 N2 . . . . 66.8(3) ?
N2 C20 C21 C22 . . . . -57.8(3) ?
C20 C21 C22 C23 . . . . 53.9(4) ?
C21 C22 C23 C24 . . . . -53.7(4) ?
C22 C23 C24 N2 . . . . 57.3(3) ?
C3 C4 C25 O3 . . . . -8.8(4) ?
C5 C4 C25 O3 . . . . 176.7(2) ?
C3 C4 C25 O4 . . . . 169.4(2) ?
C5 C4 C25 O4 . . . . -5.0(3) ?
O1 C18 N1 C1 . . . . -168.4(2) ?
C19 C18 N1 C1 . . . . 12.1(3) ?
O1 C18 N1 C5 . . . . -5.5(3) ?
C19 C18 N1 C5 . . . . 175.05(17) ?
C2 C1 N1 C18 . . . . 102.4(2) ?
C12 C1 N1 C18 . . . . -129.59(19) ?
C2 C1 N1 C5 . . . . -60.5(2) ?
C12 C1 N1 C5 . . . . 67.5(2) ?
C4 C5 N1 C18 . . . . -123.85(19) ?
C6 C5 N1 C18 . . . . 106.2(2) ?
C4 C5 N1 C1 . . . . 40.3(2) ?
C6 C5 N1 C1 . . . . -89.7(2) ?
C18 C19 N2 C20 . . . . 58.5(2) ?
C18 C19 N2 C24 . . . . 179.17(19) ?
C21 C20 N2 C19 . . . . 179.7(2) ?
C21 C20 N2 C24 . . . . 59.2(3) ?
C23 C24 N2 C19 . . . . 179.1(2) ?
C23 C24 N2 C20 . . . . -58.9(3) ?
O3 C25 O4 C26 . . . . -6.9(4) ?
C4 C25 O4 C26 . . . . 174.8(2) ?
C27 C26 O4 C25 . . . . -116.4(5) ?
loop_
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1 PubChem 139079266
