#------------------------------------------------------------------------------
#$Date: 2021-07-29 08:06:50 +0300 (Thu, 29 Jul 2021) $
#$Revision: 267814 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/32/7243279.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_7243279
loop_
_publ_author_name
'Tantawy, Ahmed H.'
'Meng, Xiang-Gao'
'Marzouk, Adel A.'
'Fouad, Ali'
'Abdelazeem, Ahmed H.'
'Youssif, Bahaa G. M.'
'Jiang, Hong'
'Wang, Man-Qun'
_publ_section_title
;
 Structure-based design, synthesis, and biological evaluation of novel
 piperine--resveratrol hybrids as antiproliferative agents targeting
 SIRT-2
;
_journal_issue                   41
_journal_name_full               'RSC Advances'
_journal_page_first              25738
_journal_page_last               25751
_journal_paper_doi               10.1039/D1RA04061H
_journal_volume                  11
_journal_year                    2021
_chemical_formula_moiety         'C23 H25 N3 O4, C H4 O'
_chemical_formula_sum            'C24 H29 N3 O5'
_chemical_formula_weight         439.50
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc22ygwd
_audit_creation_date             2019-03-28
_audit_creation_method
; 
Olex2 1.2 
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) 
;
_audit_update_record
;
2019-06-18 deposited with the CCDC.	2021-06-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.247(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.298(3)
_cell_length_b                   13.398(3)
_cell_length_c                   15.678(4)
_cell_measurement_reflns_used    2466
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.00
_cell_measurement_theta_min      2.42
_cell_volume                     2266.5(10)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XM (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0604
_diffrn_reflns_av_unetI/netI     0.0569
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            17545
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         1.887
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5832
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_description       block
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       0.0039(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     295
_refine_ls_number_reflns         4630
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0948
_refine_ls_R_factor_gt           0.0475
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0719P)²+0.0523P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1263
_refine_ls_wR_factor_ref         0.1535
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2716
_reflns_number_total             4630
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ra04061h3.cif
_cod_data_source_block           mo_190327e_0m
_cod_database_code               7243279
_shelx_shelxl_version_number     2014/7
_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_max   0.991
_shelx_estimated_absorpt_t_min   0.986
_olex2_refinement_description
; 
1. Fixed Uiso 
 At 1.2 times of: 
  All C(H) groups, All C(H,H) groups, All N(H) groups 
 At 1.5 times of: 
  All C(H,H,H) groups, All O(H) groups 
2.a Secondary CH2 refined with riding coordinates: 
 C2(H2A,H2B), C4(H4A,H4B), C23(H23A,H23B) 
2.b Aromatic/amide H refined with riding coordinates: 
 C6(H6), C9(H9), C10(H10), C11(H11), C13(H13), C14(H14), C15(H15), C16(H16), 
 C18(H18), C21(H21), C22(H22), N3(H3) 
2.c Idealised Me refined as rotating group: 
 C1(H1A,H1B,H1C), C3(H3A,H3B,H3C), C24(H24A,H24B,H24C) 
2.d Idealised tetrahedral OH refined as rotating group: 
 O1(H1), O5(H5) 
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
C1 C 0.0953(2) 0.39825(18) -0.31984(16) 0.0642(6) Uani 1 1 d . . . . .
H1A H 0.1225 0.3673 -0.3660 0.096 Uiso 1 1 calc GR . . . .
H1B H 0.1660 0.4159 -0.2708 0.096 Uiso 1 1 calc GR . . . .
H1C H 0.0486 0.4573 -0.3430 0.096 Uiso 1 1 calc GR . . . .
C2 C 0.01545(18) 0.32701(15) -0.28826(14) 0.0505(5) Uani 1 1 d . . . . .
H2A H -0.0128 0.3593 -0.2425 0.061 Uiso 1 1 calc R . . . .
H2B H -0.0571 0.3113 -0.3378 0.061 Uiso 1 1 calc R . . . .
C3 C -0.0332(3) 0.09182(19) -0.33995(18) 0.0786(8) Uani 1 1 d . . . . .
H3A H -0.0262 0.0419 -0.3821 0.118 Uiso 1 1 calc GR . . . .
H3B H -0.1061 0.1312 -0.3654 0.118 Uiso 1 1 calc GR . . . .
H3C H -0.0391 0.0600 -0.2865 0.118 Uiso 1 1 calc GR . . . .
C4 C 0.0784(2) 0.15757(16) -0.31795(14) 0.0568(6) Uani 1 1 d . . . . .
H4A H 0.1518 0.1166 -0.2953 0.068 Uiso 1 1 calc R . . . .
H4B H 0.0834 0.1894 -0.3723 0.068 Uiso 1 1 calc R . . . .
C5 C 0.14260(18) 0.22484(15) -0.16421(14) 0.0453(5) Uani 1 1 d . . . . .
C6 C 0.16632(19) 0.30732(15) -0.10652(14) 0.0503(5) Uani 1 1 d . . . . .
H6 H 0.1367 0.3697 -0.1291 0.060 Uiso 1 1 calc R . . . .
C7 C 0.23146(18) 0.29891(15) -0.01830(14) 0.0456(5) Uani 1 1 d . . . . .
C8 C 0.27656(17) 0.20627(15) 0.01969(13) 0.0443(5) Uani 1 1 d . . . . .
C9 C 0.25139(19) 0.12485(15) -0.03816(14) 0.0501(5) Uani 1 1 d . . . . .
H9 H 0.2794 0.0623 -0.0152 0.060 Uiso 1 1 calc R . . . .
C10 C 0.18797(19) 0.13193(15) -0.12643(15) 0.0524(6) Uani 1 1 d . . . . .
H10 H 0.1745 0.0751 -0.1621 0.063 Uiso 1 1 calc R . . . .
C11 C 0.34419(18) 0.19449(16) 0.11158(14) 0.0483(5) Uani 1 1 d . . . . .
H11 H 0.3689 0.1308 0.1333 0.058 Uiso 1 1 calc R . . . .
C12 C 0.47254(17) 0.32111(16) 0.31255(14) 0.0459(5) Uani 1 1 d . . . . .
C13 C 0.53305(18) 0.28560(16) 0.40295(14) 0.0494(5) Uani 1 1 d . . . . .
H13 H 0.5489 0.2176 0.4115 0.059 Uiso 1 1 calc R . . . .
C14 C 0.56667(17) 0.34510(16) 0.47365(14) 0.0483(5) Uani 1 1 d . . . . .
H14 H 0.5510 0.4130 0.4643 0.058 Uiso 1 1 calc R . . . .
C15 C 0.62494(18) 0.31298(16) 0.56291(14) 0.0508(5) Uani 1 1 d . . . . .
H15 H 0.6466 0.2459 0.5711 0.061 Uiso 1 1 calc R . . . .
C16 C 0.65111(17) 0.36977(15) 0.63546(14) 0.0480(5) Uani 1 1 d . . . . .
H16 H 0.6297 0.4368 0.6266 0.058 Uiso 1 1 calc R . . . .
C17 C 0.70934(17) 0.33906(15) 0.72709(14) 0.0450(5) Uani 1 1 d . . . . .
C18 C 0.73949(18) 0.23894(16) 0.74914(14) 0.0501(5) Uani 1 1 d . . . . .
H18 H 0.7197 0.1891 0.7059 0.060 Uiso 1 1 calc R . . . .
C19 C 0.79834(19) 0.21749(15) 0.83550(15) 0.0504(5) Uani 1 1 d . . . . .
C20 C 0.82769(19) 0.28881(17) 0.90149(14) 0.0522(5) Uani 1 1 d . . . . .
C21 C 0.7972(2) 0.38588(16) 0.88303(16) 0.0579(6) Uani 1 1 d . . . . .
H21 H 0.8154 0.4343 0.9275 0.069 Uiso 1 1 calc R . . . .
C22 C 0.73764(18) 0.40949(16) 0.79479(14) 0.0510(5) Uani 1 1 d . . . . .
H22 H 0.7156 0.4756 0.7803 0.061 Uiso 1 1 calc R . . . .
C23 C 0.9009(2) 0.1436(2) 0.96228(16) 0.0734(7) Uani 1 1 d . . . . .
H23A H 0.9883 0.1305 0.9717 0.088 Uiso 1 1 calc R . . . .
H23B H 0.8718 0.1000 1.0012 0.088 Uiso 1 1 calc R . . . .
C24 C 0.4339(3) 0.0046(2) 0.3784(2) 0.1005(10) Uani 1 1 d . . . . .
H24A H 0.3902 -0.0578 0.3687 0.151 Uiso 1 1 calc GR . . . .
H24B H 0.3909 0.0513 0.4050 0.151 Uiso 1 1 calc GR . . . .
H24C H 0.5162 -0.0055 0.4176 0.151 Uiso 1 1 calc GR . . . .
N2 N 0.37199(15) 0.26897(13) 0.16520(11) 0.0493(5) Uani 1 1 d . . . . .
N1 N 0.07828(16) 0.23447(13) -0.25234(11) 0.0529(5) Uani 1 1 d . . . . .
N3 N 0.43235(15) 0.24802(13) 0.25284(11) 0.0489(4) Uani 1 1 d . . . . .
H3 H 0.4446 0.1868 0.2698 0.059 Uiso 1 1 calc R . . . .
O1 O 0.25325(16) 0.38367(10) 0.03115(10) 0.0637(5) Uani 1 1 d . . . . .
H1 H 0.2927 0.3702 0.0828 0.096 Uiso 1 1 calc GR . . . .
O2 O 0.45973(14) 0.40982(11) 0.29319(10) 0.0624(4) Uani 1 1 d . . . . .
O3 O 0.83383(17) 0.12534(12) 0.87230(11) 0.0780(5) Uani 1 1 d . . . . .
O4 O 0.88325(16) 0.24463(13) 0.98205(10) 0.0721(5) Uani 1 1 d . . . . .
O5 O 0.4402(2) 0.04112(13) 0.29928(14) 0.0879(6) Uani 1 1 d . . . . .
H5 H 0.4728 -0.0004 0.2750 0.132 Uiso 1 1 calc GR . . . .
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_
_citation_id
_citation_doi
_citation_year
1 10.1016/j.bioorg.2019.103464 2019
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
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C1 C2 H2A 108.9 . . ?
C1 C2 H2B 108.9 . . ?
H2A C2 H2B 107.7 . . ?
N1 C2 C1 113.51(18) . . ?
N1 C2 H2A 108.9 . . ?
N1 C2 H2B 108.9 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C4 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
C4 C3 H3C 109.5 . . ?
C3 C4 H4A 108.8 . . ?
C3 C4 H4B 108.8 . . ?
H4A C4 H4B 107.7 . . ?
N1 C4 C3 113.8(2) . . ?
N1 C4 H4A 108.8 . . ?
N1 C4 H4B 108.8 . . ?
C6 C5 C10 116.68(19) . . ?
N1 C5 C6 121.43(18) . . ?
N1 C5 C10 121.88(18) . . ?
C5 C6 H6 119.0 . . ?
C7 C6 C5 122.06(19) . . ?
C7 C6 H6 119.0 . . ?
C6 C7 C8 121.40(19) . . ?
O1 C7 C6 117.52(18) . . ?
O1 C7 C8 121.06(19) . . ?
C7 C8 C11 122.99(19) . . ?
C9 C8 C7 115.94(19) . . ?
C9 C8 C11 121.07(19) . . ?
C8 C9 H9 118.2 . . ?
C10 C9 C8 123.51(19) . . ?
C10 C9 H9 118.2 . . ?
C5 C10 H10 119.8 . . ?
C9 C10 C5 120.39(19) . . ?
C9 C10 H10 119.8 . . ?
C8 C11 H11 119.0 . . ?
N2 C11 C8 122.01(19) . . ?
N2 C11 H11 119.0 . . ?
N3 C12 C13 113.91(19) . . ?
O2 C12 C13 123.0(2) . . ?
O2 C12 N3 123.1(2) . . ?
C12 C13 H13 118.3 . . ?
C14 C13 C12 123.5(2) . . ?
C14 C13 H13 118.3 . . ?
C13 C14 H14 117.5 . . ?
C13 C14 C15 125.0(2) . . ?
C15 C14 H14 117.5 . . ?
C14 C15 H15 116.9 . . ?
C16 C15 C14 126.1(2) . . ?
C16 C15 H15 116.9 . . ?
C15 C16 H16 116.3 . . ?
C15 C16 C17 127.3(2) . . ?
C17 C16 H16 116.3 . . ?
C18 C17 C16 121.41(19) . . ?
C22 C17 C16 119.97(19) . . ?
C22 C17 C18 118.61(19) . . ?
C17 C18 H18 121.2 . . ?
C19 C18 C17 117.53(19) . . ?
C19 C18 H18 121.2 . . ?
C18 C19 C20 122.9(2) . . ?
C18 C19 O3 127.51(19) . . ?
O3 C19 C20 109.50(19) . . ?
C21 C20 C19 121.1(2) . . ?
C21 C20 O4 129.1(2) . . ?
O4 C20 C19 109.67(19) . . ?
C20 C21 H21 121.6 . . ?
C20 C21 C22 116.8(2) . . ?
C22 C21 H21 121.6 . . ?
C17 C22 H22 118.5 . . ?
C21 C22 C17 122.9(2) . . ?
C21 C22 H22 118.5 . . ?
H23A C23 H23B 108.4 . . ?
O3 C23 H23A 110.0 . . ?
O3 C23 H23B 110.0 . . ?
O3 C23 O4 108.40(18) . . ?
O4 C23 H23A 110.0 . . ?
O4 C23 H23B 110.0 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O5 C24 H24A 109.5 . . ?
O5 C24 H24B 109.5 . . ?
O5 C24 H24C 109.5 . . ?
C11 N2 N3 116.77(18) . . ?
C4 N1 C2 115.57(17) . . ?
C5 N1 C2 121.65(16) . . ?
C5 N1 C4 122.49(17) . . ?
C12 N3 N2 121.11(18) . . ?
C12 N3 H3 119.4 . . ?
N2 N3 H3 119.4 . . ?
C7 O1 H1 109.5 . . ?
C19 O3 C23 105.55(17) . . ?
C20 O4 C23 105.52(17) . . ?
C24 O5 H5 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
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 C2 1.495(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 N1 1.456(3) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C3 C4 1.492(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 N1 1.456(3) . ?
C5 C6 1.403(3) . ?
C5 C10 1.408(3) . ?
C5 N1 1.363(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.365(3) . ?
C7 C8 1.405(3) . ?
C7 O1 1.356(2) . ?
C8 C9 1.393(3) . ?
C8 C11 1.425(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.360(3) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C11 N2 1.282(3) . ?
C12 C13 1.459(3) . ?
C12 N3 1.338(3) . ?
C12 O2 1.225(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.326(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.425(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.327(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.451(3) . ?
C17 C18 1.402(3) . ?
C17 C22 1.385(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.351(3) . ?
C19 C20 1.375(3) . ?
C19 O3 1.371(2) . ?
C20 C21 1.355(3) . ?
C20 O4 1.367(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.384(3) . ?
C22 H22 0.9300 . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 O3 1.411(3) . ?
C23 O4 1.416(3) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C24 O5 1.355(3) . ?
N2 N3 1.370(2) . ?
N3 H3 0.8600 . ?
O1 H1 0.8200 . ?
O5 H5 0.8200 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3 H3 O5 0.86 2.01 2.861(3) 169.7 .
O1 H1 N2 0.82 1.90 2.628(2) 146.7 .
O5 H5 O2 0.82 1.91 2.729(2) 174.0 2_645
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
C1 C2 N1 C4 -84.4(2) . . . . ?
C1 C2 N1 C5 89.6(2) . . . . ?
C3 C4 N1 C2 -87.0(2) . . . . ?
C3 C4 N1 C5 99.1(2) . . . . ?
C5 C6 C7 C8 -1.1(3) . . . . ?
C5 C6 C7 O1 177.69(18) . . . . ?
C6 C5 C10 C9 0.0(3) . . . . ?
C6 C5 N1 C2 -9.2(3) . . . . ?
C6 C5 N1 C4 164.3(2) . . . . ?
C6 C7 C8 C9 0.4(3) . . . . ?
C6 C7 C8 C11 -179.58(18) . . . . ?
C7 C8 C9 C10 0.4(3) . . . . ?
C7 C8 C11 N2 -2.4(3) . . . . ?
C8 C9 C10 C5 -0.6(3) . . . . ?
C8 C11 N2 N3 177.17(16) . . . . ?
C9 C8 C11 N2 177.55(18) . . . . ?
C10 C5 C6 C7 0.8(3) . . . . ?
C10 C5 N1 C2 170.48(19) . . . . ?
C10 C5 N1 C4 -16.0(3) . . . . ?
C11 C8 C9 C10 -179.60(18) . . . . ?
C11 N2 N3 C12 175.46(17) . . . . ?
C12 C13 C14 C15 179.44(18) . . . . ?
C13 C12 N3 N2 179.10(15) . . . . ?
C13 C14 C15 C16 -174.7(2) . . . . ?
C14 C15 C16 C17 179.45(18) . . . . ?
C15 C16 C17 C18 -3.5(3) . . . . ?
C15 C16 C17 C22 175.7(2) . . . . ?
C16 C17 C18 C19 177.20(18) . . . . ?
C16 C17 C22 C21 -177.58(18) . . . . ?
C17 C18 C19 C20 0.9(3) . . . . ?
C17 C18 C19 O3 178.3(2) . . . . ?
C18 C17 C22 C21 1.7(3) . . . . ?
C18 C19 C20 C21 0.8(3) . . . . ?
C18 C19 C20 O4 178.21(18) . . . . ?
C18 C19 O3 C23 174.9(2) . . . . ?
C19 C20 C21 C22 -1.2(3) . . . . ?
C19 C20 O4 C23 6.7(2) . . . . ?
C20 C19 O3 C23 -7.3(2) . . . . ?
C20 C21 C22 C17 0.0(3) . . . . ?
C21 C20 O4 C23 -176.1(2) . . . . ?
C22 C17 C18 C19 -2.0(3) . . . . ?
N1 C5 C6 C7 -179.45(18) . . . . ?
N1 C5 C10 C9 -179.74(18) . . . . ?
N3 C12 C13 C14 -171.99(18) . . . . ?
O1 C7 C8 C9 -178.26(18) . . . . ?
O1 C7 C8 C11 1.7(3) . . . . ?
O2 C12 C13 C14 8.0(3) . . . . ?
O2 C12 N3 N2 -0.9(3) . . . . ?
O3 C19 C20 C21 -177.1(2) . . . . ?
O3 C19 C20 O4 0.4(2) . . . . ?
O3 C23 O4 C20 -11.3(3) . . . . ?
O4 C20 C21 C22 -178.1(2) . . . . ?
O4 C23 O3 C19 11.5(3) . . . . ?
