#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/03/2230327.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_2230327
loop_
_publ_author_name
'Naicker, Tricia'
'Govender, Thavendran'
'Kruger, Hendrik. G.'
'Maguire, Glenn. E. M.'
_publ_section_title
;
 (1S,3S)-Methyl
 2-benzyl-6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylate
;
_journal_coeditor_code           GW2101
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1403
_journal_paper_doi               10.1107/S1600536811017430
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C26 H27 N O4'
_chemical_formula_moiety         'C26 H27 N O4'
_chemical_formula_sum            'C26 H27 N O4'
_chemical_formula_weight         417.49
_chemical_melting_point          420
_chemical_name_common            TIQester
_chemical_name_systematic
;
(1S,3S)-Methyl 2-benzyl-6,7-dimethoxy-
1-phenyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylate
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 96.9860(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.7797(7)
_cell_length_b                   5.4646(4)
_cell_length_c                   20.6959(15)
_cell_measurement_reflns_used    20624
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.40
_cell_measurement_theta_min      1.98
_cell_volume                     1097.82(14)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2000)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008b)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008b)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008b)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Kappa DUO APEXII'
_diffrn_measurement_method       '0.5° φ scans and ω'
_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  0.0296
_diffrn_reflns_av_sigmaI/netI    0.0149
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            20624
_diffrn_reflns_theta_full        28.40
_diffrn_reflns_theta_max         28.40
_diffrn_reflns_theta_min         1.98
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.9949
_exptl_absorpt_correction_T_min  0.9314
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2008a)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.85
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.185
_refine_ls_extinction_coef       none
_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     280
_refine_ls_number_reflns         3032
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0358
_refine_ls_R_factor_gt           0.0314
_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/[σ²(Fo²)+(0.0488P)²+0.1593P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0832
_refine_ls_wR_factor_ref         0.0866
_reflns_number_gt                2764
_reflns_number_total             3032
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gw2101.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      P21
_cod_database_code               2230327
_cod_database_fobs_code          2230327
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
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_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.59208(12) 0.2130(3) 0.07345(6) 0.0400(3) Uani d . 1 1 . .
O O2 0.53131(12) -0.1159(3) 0.15604(6) 0.0370(3) Uani d . 1 1 . .
O O3 1.13983(13) 0.2008(3) 0.41963(6) 0.0382(3) Uani d . 1 1 . .
O O4 1.06894(12) 0.5827(3) 0.43713(6) 0.0371(3) Uani d . 1 1 . .
N N1 1.07939(12) 0.4482(3) 0.28290(6) 0.0250(3) Uani d . 1 1 . .
C C1 0.99153(14) 0.5106(3) 0.22148(7) 0.0248(3) Uani d . 1 1 . .
H H1 0.9572 0.6819 0.2252 0.030 Uiso calc R 1 1 . .
C C2 0.86750(14) 0.3416(3) 0.20811(7) 0.0241(3) Uani d . 1 1 . .
C C3 0.78789(15) 0.3561(3) 0.14696(7) 0.0290(3) Uani d . 1 1 . .
H H3 0.8117 0.4713 0.1158 0.035 Uiso calc R 1 1 . .
C C4 0.67576(15) 0.2054(4) 0.13156(7) 0.0290(3) Uani d . 1 1 . .
C C5 0.64159(15) 0.0305(3) 0.17670(7) 0.0278(3) Uani d . 1 1 . .
C C6 0.71774(15) 0.0206(3) 0.23736(7) 0.0261(3) Uani d . 1 1 . .
H H6 0.6943 -0.0953 0.2684 0.031 Uiso calc R 1 1 . .
C C7 0.82981(14) 0.1801(3) 0.25388(7) 0.0238(3) Uani d . 1 1 . .
C C8 0.90596(15) 0.1782(3) 0.32152(7) 0.0262(3) Uani d . 1 1 . .
H H8A 0.9673 0.0336 0.3267 0.031 Uiso calc R 1 1 . .
H H8B 0.8390 0.1647 0.3536 0.031 Uiso calc R 1 1 . .
C C9 0.99109(14) 0.4091(3) 0.33493(7) 0.0246(3) Uani d . 1 1 . .
H H9 0.9278 0.5523 0.3364 0.030 Uiso calc R 1 1 . .
C C10 1.07737(14) 0.3815(4) 0.40099(7) 0.0279(3) Uani d . 1 1 . .
C C11 1.1481(2) 0.5762(5) 0.50083(9) 0.0495(5) Uani d . 1 1 . .
H H11A 1.1357 0.7303 0.5236 0.074 Uiso calc R 1 1 . .
H H11B 1.2459 0.5541 0.4961 0.074 Uiso calc R 1 1 . .
H H11C 1.1165 0.4397 0.5259 0.074 Uiso calc R 1 1 . .
C C12 1.17749(15) 0.6521(3) 0.29833(8) 0.0291(3) Uani d . 1 1 . .
H H12A 1.1310 0.7808 0.3213 0.035 Uiso calc R 1 1 . .
H H12B 1.1998 0.7234 0.2569 0.035 Uiso calc R 1 1 . .
C C13 1.31095(14) 0.5860(3) 0.33944(7) 0.0270(3) Uani d . 1 1 . .
C C14 1.38533(17) 0.3781(4) 0.32668(9) 0.0355(4) Uani d . 1 1 . .
H H14 1.3478 0.2647 0.2945 0.043 Uiso calc R 1 1 . .
C C15 1.51460(19) 0.3358(4) 0.36092(11) 0.0469(5) Uani d . 1 1 . .
H H15 1.5656 0.1948 0.3516 0.056 Uiso calc R 1 1 . .
C C16 1.56899(19) 0.4983(5) 0.40837(11) 0.0501(5) Uani d . 1 1 . .
H H16 1.6573 0.4691 0.4317 0.060 Uiso calc R 1 1 . .
C C17 1.4954(2) 0.7017(5) 0.42181(10) 0.0482(5) Uani d . 1 1 . .
H H17 1.5325 0.8125 0.4547 0.058 Uiso calc R 1 1 . .
C C18 1.36621(17) 0.7465(4) 0.38741(9) 0.0369(4) Uani d . 1 1 . .
H H18 1.3158 0.8879 0.3969 0.044 Uiso calc R 1 1 . .
C C19 1.07526(15) 0.4993(3) 0.16403(8) 0.0280(3) Uani d . 1 1 . .
C C20 1.16294(16) 0.3043(3) 0.15664(8) 0.0322(4) Uani d . 1 1 . .
H H20 1.1761 0.1814 0.1893 0.039 Uiso calc R 1 1 . .
C C21 1.23198(19) 0.2875(4) 0.10159(9) 0.0409(4) Uani d . 1 1 . .
H H21 1.2937 0.1558 0.0973 0.049 Uiso calc R 1 1 . .
C C22 1.2103(2) 0.4635(5) 0.05320(10) 0.0481(5) Uani d . 1 1 . .
H H22 1.2556 0.4504 0.0152 0.058 Uiso calc R 1 1 . .
C C23 1.1231(2) 0.6574(5) 0.06006(10) 0.0489(5) Uani d . 1 1 . .
H H23 1.1079 0.7772 0.0267 0.059 Uiso calc R 1 1 . .
C C24 1.05718(18) 0.6783(4) 0.11589(9) 0.0380(4) Uani d . 1 1 . .
H H24 0.9997 0.8153 0.1211 0.046 Uiso calc R 1 1 . .
C C25 0.60475(19) 0.4241(4) 0.03433(8) 0.0400(4) Uani d . 1 1 . .
H H25A 0.5409 0.4110 -0.0059 0.060 Uiso calc R 1 1 . .
H H25B 0.6994 0.4361 0.0236 0.060 Uiso calc R 1 1 . .
H H25C 0.5827 0.5705 0.0584 0.060 Uiso calc R 1 1 . .
C C26 0.4896(2) -0.2845(4) 0.20218(9) 0.0442(5) Uani d . 1 1 . .
H H26A 0.4106 -0.3792 0.1821 0.066 Uiso calc R 1 1 . .
H H26B 0.4636 -0.1948 0.2398 0.066 Uiso calc R 1 1 . .
H H26C 0.5660 -0.3957 0.2164 0.066 Uiso calc R 1 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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
C4 O1 C25 . . 116.09(14) ?
C5 O2 C26 . . 116.63(13) ?
C10 O4 C11 . . 115.28(16) ?
C9 N1 C12 . . 111.91(12) ?
C9 N1 C1 . . 109.20(11) ?
C12 N1 C1 . . 107.71(12) ?
N1 C1 C2 . . 112.42(12) ?
N1 C1 C19 . . 110.39(11) ?
C2 C1 C19 . . 108.97(12) ?
N1 C1 H1 . . 108.3 ?
C2 C1 H1 . . 108.3 ?
C19 C1 H1 . . 108.3 ?
C7 C2 C3 . . 119.35(13) ?
C7 C2 C1 . . 122.51(13) ?
C3 C2 C1 . . 118.13(13) ?
C4 C3 C2 . . 120.88(15) ?
C4 C3 H3 . . 119.6 ?
C2 C3 H3 . . 119.6 ?
O1 C4 C3 . . 123.96(15) ?
O1 C4 C5 . . 116.04(14) ?
C3 C4 C5 . . 119.99(13) ?
O2 C5 C6 . . 125.36(15) ?
O2 C5 C4 . . 115.59(13) ?
C6 C5 C4 . . 119.04(14) ?
C5 C6 C7 . . 120.93(14) ?
C5 C6 H6 . . 119.5 ?
C7 C6 H6 . . 119.5 ?
C2 C7 C6 . . 119.65(13) ?
C2 C7 C8 . . 120.07(13) ?
C6 C7 C8 . . 120.27(13) ?
C7 C8 C9 . . 111.28(13) ?
C7 C8 H8A . . 109.4 ?
C9 C8 H8A . . 109.4 ?
C7 C8 H8B . . 109.4 ?
C9 C8 H8B . . 109.4 ?
H8A C8 H8B . . 108.0 ?
N1 C9 C8 . . 110.08(12) ?
N1 C9 C10 . . 111.08(11) ?
C8 C9 C10 . . 108.24(14) ?
N1 C9 H9 . . 109.1 ?
C8 C9 H9 . . 109.1 ?
C10 C9 H9 . . 109.1 ?
O3 C10 O4 . . 124.06(14) ?
O3 C10 C9 . . 125.08(16) ?
O4 C10 C9 . . 110.79(14) ?
O4 C11 H11A . . 109.5 ?
O4 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
O4 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
N1 C12 C13 . . 115.70(14) ?
N1 C12 H12A . . 108.4 ?
C13 C12 H12A . . 108.4 ?
N1 C12 H12B . . 108.4 ?
C13 C12 H12B . . 108.4 ?
H12A C12 H12B . . 107.4 ?
C18 C13 C14 . . 119.07(15) ?
C18 C13 C12 . . 119.12(16) ?
C14 C13 C12 . . 121.58(15) ?
C15 C14 C13 . . 120.17(18) ?
C15 C14 H14 . . 119.9 ?
C13 C14 H14 . . 119.9 ?
C16 C15 C14 . . 120.2(2) ?
C16 C15 H15 . . 119.9 ?
C14 C15 H15 . . 119.9 ?
C17 C16 C15 . . 119.92(17) ?
C17 C16 H16 . . 120.0 ?
C15 C16 H16 . . 120.0 ?
C16 C17 C18 . . 120.29(19) ?
C16 C17 H17 . . 119.9 ?
C18 C17 H17 . . 119.9 ?
C13 C18 C17 . . 120.35(19) ?
C13 C18 H18 . . 119.8 ?
C17 C18 H18 . . 119.8 ?
C20 C19 C24 . . 119.15(15) ?
C20 C19 C1 . . 121.00(15) ?
C24 C19 C1 . . 119.72(16) ?
C19 C20 C21 . . 120.48(18) ?
C19 C20 H20 . . 119.8 ?
C21 C20 H20 . . 119.8 ?
C22 C21 C20 . . 119.81(19) ?
C22 C21 H21 . . 120.1 ?
C20 C21 H21 . . 120.1 ?
C23 C22 C21 . . 120.08(17) ?
C23 C22 H22 . . 120.0 ?
C21 C22 H22 . . 120.0 ?
C22 C23 C24 . . 120.2(2) ?
C22 C23 H23 . . 119.9 ?
C24 C23 H23 . . 119.9 ?
C19 C24 C23 . . 120.3(2) ?
C19 C24 H24 . . 119.9 ?
C23 C24 H24 . . 119.9 ?
O1 C25 H25A . . 109.5 ?
O1 C25 H25B . . 109.5 ?
H25A C25 H25B . . 109.5 ?
O1 C25 H25C . . 109.5 ?
H25A C25 H25C . . 109.5 ?
H25B C25 H25C . . 109.5 ?
O2 C26 H26A . . 109.5 ?
O2 C26 H26B . . 109.5 ?
H26A C26 H26B . . 109.5 ?
O2 C26 H26C . . 109.5 ?
H26A C26 H26C . . 109.5 ?
H26B C26 H26C . . 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
O1 C4 . 1.3705(17) ?
O1 C25 . 1.423(3) ?
O2 C5 . 1.3688(18) ?
O2 C26 . 1.422(2) ?
O3 C10 . 1.200(2) ?
O4 C10 . 1.338(2) ?
O4 C11 . 1.446(2) ?
N1 C9 . 1.4755(18) ?
N1 C12 . 1.480(2) ?
N1 C1 . 1.4849(18) ?
C1 C2 . 1.523(2) ?
C1 C19 . 1.525(2) ?
C1 H1 . 1.0000 ?
C2 C7 . 1.378(2) ?
C2 C3 . 1.405(2) ?
C3 C4 . 1.377(2) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.405(2) ?
C5 C6 . 1.381(2) ?
C6 C7 . 1.409(2) ?
C6 H6 . 0.9500 ?
C7 C8 . 1.5035(19) ?
C8 C9 . 1.519(2) ?
C8 H8A . 0.9900 ?
C8 H8B . 0.9900 ?
C9 C10 . 1.524(2) ?
C9 H9 . 1.0000 ?
C11 H11A . 0.9800 ?
C11 H11B . 0.9800 ?
C11 H11C . 0.9800 ?
C12 C13 . 1.513(2) ?
C12 H12A . 0.9900 ?
C12 H12B . 0.9900 ?
C13 C18 . 1.384(2) ?
C13 C14 . 1.391(2) ?
C14 C15 . 1.391(3) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.382(3) ?
C15 H15 . 0.9500 ?
C16 C17 . 1.371(3) ?
C16 H16 . 0.9500 ?
C17 C18 . 1.394(2) ?
C17 H17 . 0.9500 ?
C18 H18 . 0.9500 ?
C19 C20 . 1.388(2) ?
C19 C24 . 1.392(3) ?
C20 C21 . 1.396(2) ?
C20 H20 . 0.9500 ?
C21 C22 . 1.386(3) ?
C21 H21 . 0.9500 ?
C22 C23 . 1.378(4) ?
C22 H22 . 0.9500 ?
C23 C24 . 1.395(3) ?
C23 H23 . 0.9500 ?
C24 H24 . 0.9500 ?
C25 H25A . 0.9800 ?
C25 H25B . 0.9800 ?
C25 H25C . 0.9800 ?
C26 H26A . 0.9800 ?
C26 H26B . 0.9800 ?
C26 H26C . 0.9800 ?
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
C18 H18 O3 1_565 0.95 2.51 3.445(2) 168
C25 H25A O1 2_655 0.98 2.43 3.183(2) 133
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
C9 N1 C1 C2 . . . . -46.18(17) ?
C12 N1 C1 C2 . . . . -167.91(12) ?
C9 N1 C1 C19 . . . . -168.08(13) ?
C12 N1 C1 C19 . . . . 70.19(16) ?
N1 C1 C2 C7 . . . . 10.8(2) ?
C19 C1 C2 C7 . . . . 133.55(15) ?
N1 C1 C2 C3 . . . . -170.35(13) ?
C19 C1 C2 C3 . . . . -47.65(19) ?
C7 C2 C3 C4 . . . . -2.2(2) ?
C1 C2 C3 C4 . . . . 178.97(15) ?
C25 O1 C4 C3 . . . . -14.8(2) ?
C25 O1 C4 C5 . . . . 165.37(15) ?
C2 C3 C4 O1 . . . . 178.63(16) ?
C2 C3 C4 C5 . . . . -1.5(3) ?
C26 O2 C5 C6 . . . . 2.6(2) ?
C26 O2 C5 C4 . . . . -176.36(16) ?
O1 C4 C5 O2 . . . . 2.0(2) ?
C3 C4 C5 O2 . . . . -177.87(15) ?
O1 C4 C5 C6 . . . . -177.02(15) ?
C3 C4 C5 C6 . . . . 3.1(2) ?
O2 C5 C6 C7 . . . . 180.00(15) ?
C4 C5 C6 C7 . . . . -1.1(2) ?
C3 C2 C7 C6 . . . . 4.2(2) ?
C1 C2 C7 C6 . . . . -177.02(14) ?
C3 C2 C7 C8 . . . . -174.44(14) ?
C1 C2 C7 C8 . . . . 4.3(2) ?
C5 C6 C7 C2 . . . . -2.6(2) ?
C5 C6 C7 C8 . . . . 176.03(14) ?
C2 C7 C8 C9 . . . . 16.00(19) ?
C6 C7 C8 C9 . . . . -162.63(14) ?
C12 N1 C9 C8 . . . . -172.39(12) ?
C1 N1 C9 C8 . . . . 68.45(16) ?
C12 N1 C9 C10 . . . . -52.52(18) ?
C1 N1 C9 C10 . . . . -171.68(14) ?
C7 C8 C9 N1 . . . . -52.11(16) ?
C7 C8 C9 C10 . . . . -173.69(12) ?
C11 O4 C10 O3 . . . . 3.4(2) ?
C11 O4 C10 C9 . . . . -179.57(14) ?
N1 C9 C10 O3 . . . . -76.9(2) ?
C8 C9 C10 O3 . . . . 44.1(2) ?
N1 C9 C10 O4 . . . . 106.16(15) ?
C8 C9 C10 O4 . . . . -132.88(14) ?
C9 N1 C12 C13 . . . . 85.52(16) ?
C1 N1 C12 C13 . . . . -154.45(13) ?
N1 C12 C13 C18 . . . . -140.47(16) ?
N1 C12 C13 C14 . . . . 45.0(2) ?
C18 C13 C14 C15 . . . . -1.3(3) ?
C12 C13 C14 C15 . . . . 173.24(17) ?
C13 C14 C15 C16 . . . . 0.9(3) ?
C14 C15 C16 C17 . . . . 0.1(3) ?
C15 C16 C17 C18 . . . . -0.5(3) ?
C14 C13 C18 C17 . . . . 0.8(3) ?
C12 C13 C18 C17 . . . . -173.86(17) ?
C16 C17 C18 C13 . . . . 0.1(3) ?
N1 C1 C19 C20 . . . . 45.6(2) ?
C2 C1 C19 C20 . . . . -78.34(17) ?
N1 C1 C19 C24 . . . . -138.67(15) ?
C2 C1 C19 C24 . . . . 97.42(18) ?
C24 C19 C20 C21 . . . . -0.1(2) ?
C1 C19 C20 C21 . . . . 175.66(15) ?
C19 C20 C21 C22 . . . . -1.6(3) ?
C20 C21 C22 C23 . . . . 1.4(3) ?
C21 C22 C23 C24 . . . . 0.5(3) ?
C20 C19 C24 C23 . . . . 2.0(3) ?
C1 C19 C24 C23 . . . . -173.83(16) ?
C22 C23 C24 C19 . . . . -2.2(3) ?
loop_
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_cod_related_entry_code
1 ChemSpider 30656703
