#------------------------------------------------------------------------------
#$Date: 2025-03-04 21:32:27 +0200 (Tue, 04 Mar 2025) $
#$Revision: 298163 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/36/1573694.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_1573694
loop_
_publ_author_name
'Seo, Seung Mo'
'Kim, Dongwook'
'Kim, Taewan'
'Han, Sunkyu'
_publ_section_title
;
 Total synthesis of (-)-flueggenine A and (-)-15'-epi-flueggenine
 D.
;
_journal_issue                   3
_journal_name_full               'Chemical science'
_journal_page_first              1216
_journal_page_last               1221
_journal_paper_doi               10.1039/d4sc07525k
_journal_volume                  16
_journal_year                    2025
_chemical_formula_moiety         'C36 H50 N2 O12'
_chemical_formula_sum            'C36 H50 N2 O12'
_chemical_formula_weight         702.78
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2024-09-23 deposited with the CCDC.	2024-12-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.613(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   17.7153(14)
_cell_length_b                   5.8663(5)
_cell_length_c                   18.0482(15)
_cell_measurement_reflns_used    9904
_cell_measurement_temperature    203(2)
_cell_measurement_theta_max      27.12
_cell_measurement_theta_min      2.74
_cell_volume                     1849.3(3)
_computing_cell_refinement       'Bruker APEX5 software'
_computing_data_collection       'Bruker APEX5 software'
_computing_data_reduction        'Bruker APEX5 software'
_computing_molecular_graphics    ORTEP
_computing_publication_material  CIFTAB
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2013)'
_diffrn_ambient_temperature      203(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'PHOTON II CPAD detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1039
_diffrn_reflns_av_unetI/netI     0.1113
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            26991
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.196
_diffrn_reflns_theta_min         2.737
_diffrn_source                   'Ius 3.0 microfocus source'
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6819
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.076
_exptl_crystal_size_mid          0.039
_exptl_crystal_size_min          0.035
_refine_diff_density_max         0.366
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
;
 Flack x determined using 1450 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.5(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     532
_refine_ls_number_reflns         8090
_refine_ls_number_restraints     199
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.1435
_refine_ls_R_factor_gt           0.0736
_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)+(0.0306P)²+0.5793P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1166
_refine_ls_wR_factor_ref         0.1370
_reflns_Friedel_coverage         0.807
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.972
_reflns_number_gt                4686
_reflns_number_total             8090
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4sc07525k2.cif
_cod_data_source_block           A24153O_004
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'MULTI-SCAN' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 1573690--1573694.cif.
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1573694
_shelx_shelxl_version_number     2019/3
_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.
;
_shelx_estimated_absorpt_t_min   0.993
_shelx_estimated_absorpt_t_max   0.997
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
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
O1 O 0.1361(2) 0.3345(7) 0.3793(2) 0.0493(10) Uani 1 1 d . . . . .
C2 C 0.1712(3) 0.4488(9) 0.4283(3) 0.0344(13) Uani 1 1 d . . . . .
O3 O 0.18623(18) 0.3728(6) 0.50107(19) 0.0346(8) Uani 1 1 d . . . . .
C4 C 0.2270(3) 0.5480(9) 0.5489(3) 0.0313(12) Uani 1 1 d . . . . .
C5 C 0.1733(3) 0.6268(9) 0.6041(3) 0.0349(13) Uani 1 1 d . . . . .
H5 H 0.207(3) 0.732(10) 0.648(3) 0.052 Uiso 1 1 d . U . . .
C6 C 0.1000(3) 0.7482(11) 0.5666(3) 0.0487(16) Uani 1 1 d . . . . .
H6A H 0.094560 0.737613 0.511248 0.058 Uiso 1 1 calc R U . A 1
H6B H 0.101500 0.911166 0.581034 0.058 Uiso 1 1 calc R U . A 1
C7 C 0.0325(7) 0.626(3) 0.5945(13) 0.047(4) Uani 0.54(3) 1 d . U P B 1
H7A H 0.018544 0.705034 0.638834 0.057 Uiso 0.54(3) 1 calc R U P B 1
H7B H -0.012984 0.620075 0.554426 0.057 Uiso 0.54(3) 1 calc R U P B 1
C7B C 0.0423(9) 0.580(3) 0.5559(15) 0.041(5) Uani 0.46(3) 1 d . U P B 2
H7C H 0.038455 0.513368 0.504991 0.049 Uiso 0.46(3) 1 calc R U P B 2
H7D H -0.007668 0.648980 0.560434 0.049 Uiso 0.46(3) 1 calc R U P B 2
C8 C 0.0620(3) 0.3952(12) 0.6146(3) 0.0508(16) Uani 1 1 d . . . . .
H8A H 0.037277 0.329248 0.654993 0.061 Uiso 1 1 calc R U . B 1
H8B H 0.052993 0.292753 0.570377 0.061 Uiso 1 1 calc R U . B 1
N9 N 0.1442(2) 0.4303(8) 0.6404(2) 0.0380(11) Uani 1 1 d . . . . .
C10 C 0.1813(3) 0.3449(10) 0.7070(3) 0.0369(13) Uani 1 1 d . . . . .
O11 O 0.2416(2) 0.4157(7) 0.7398(2) 0.0445(9) Uani 1 1 d . . . . .
O12 O 0.1413(2) 0.1688(7) 0.7289(2) 0.0454(10) Uani 1 1 d . . . . .
C13 C 0.1597(3) 0.0734(10) 0.8057(3) 0.0414(14) Uani 1 1 d . . . . .
C14 C 0.2390(4) -0.0353(10) 0.8177(3) 0.0531(16) Uani 1 1 d . . . . .
H14A H 0.248469 -0.111663 0.866710 0.080 Uiso 1 1 calc R U . . .
H14B H 0.277820 0.083002 0.816276 0.080 Uiso 1 1 calc R U . . .
H14C H 0.241806 -0.147138 0.777938 0.080 Uiso 1 1 calc R U . . .
C15 C 0.1523(4) 0.2583(10) 0.8618(3) 0.0511(16) Uani 1 1 d . . . . .
H15A H 0.158606 0.192571 0.912362 0.077 Uiso 1 1 calc R U . . .
H15B H 0.101672 0.329060 0.849566 0.077 Uiso 1 1 calc R U . . .
H15C H 0.191933 0.373926 0.859968 0.077 Uiso 1 1 calc R U . . .
C16 C 0.0978(4) -0.1060(12) 0.8040(3) 0.0572(17) Uani 1 1 d . . . . .
H16A H 0.102700 -0.179748 0.853265 0.086 Uiso 1 1 calc R U . . .
H16B H 0.103377 -0.220564 0.765706 0.086 Uiso 1 1 calc R U . . .
H16C H 0.047407 -0.033779 0.791781 0.086 Uiso 1 1 calc R U . . .
C17 C 0.3037(3) 0.4608(8) 0.5891(3) 0.0321(12) Uani 1 1 d . . . . .
H17A H 0.333402 0.396277 0.552176 0.038 Uiso 1 1 calc R U . . .
H17B H 0.295688 0.338966 0.624922 0.038 Uiso 1 1 calc R U . . .
C18 C 0.3476(3) 0.6579(9) 0.6310(3) 0.0367(13) Uani 1 1 d . . . . .
H18 H 0.325(3) 0.699(10) 0.680(3) 0.055 Uiso 1 1 d . U . . .
O19 O 0.4286(13) 0.575(5) 0.6521(10) 0.042(3) Uani 0.71(3) 1 d D U P C 1
O20 O 0.4471(6) 0.849(3) 0.7406(9) 0.072(4) Uani 0.71(3) 1 d D U P C 1
C21 C 0.4700(7) 0.687(3) 0.7114(8) 0.052(4) Uani 0.71(3) 1 d D U P C 1
C22 C 0.5467(7) 0.579(3) 0.7338(11) 0.060(4) Uani 0.71(3) 1 d D U P C 1
H22A H 0.582141 0.688823 0.761768 0.089 Uiso 0.71(3) 1 calc R U P C 1
H22B H 0.566394 0.529953 0.688734 0.089 Uiso 0.71(3) 1 calc R U P C 1
H22C H 0.541848 0.445954 0.765658 0.089 Uiso 0.71(3) 1 calc R U P C 1
O19B O 0.421(3) 0.591(13) 0.652(2) 0.041(7) Uani 0.29(3) 1 d D U P C 2
O20B O 0.4309(16) 0.732(8) 0.7688(15) 0.076(9) Uani 0.29(3) 1 d D U P C 2
C21B C 0.457(2) 0.622(7) 0.7239(19) 0.058(7) Uani 0.29(3) 1 d D U P C 2
C22B C 0.530(2) 0.489(8) 0.739(3) 0.072(11) Uani 0.29(3) 1 d D U P C 2
H22D H 0.556782 0.521460 0.789776 0.109 Uiso 0.29(3) 1 calc R U P C 2
H22E H 0.562907 0.532969 0.702388 0.109 Uiso 0.29(3) 1 calc R U P C 2
H22F H 0.518698 0.325904 0.733898 0.109 Uiso 0.29(3) 1 calc R U P C 2
C23 C 0.3465(3) 0.8699(10) 0.5851(3) 0.0381(13) Uani 1 1 d . . . . .
H23 H 0.382692 0.986041 0.601888 0.046 Uiso 1 1 calc R U . . .
C24 C 0.2967(3) 0.9048(9) 0.5213(3) 0.0357(12) Uani 1 1 d . . . . .
H24 H 0.297730 1.043529 0.494306 0.043 Uiso 1 1 calc R U . . .
C25 C 0.2414(2) 0.7286(9) 0.4937(3) 0.0290(11) Uani 1 1 d . . . . .
C26 C 0.2056(3) 0.6776(9) 0.4249(3) 0.0297(12) Uani 1 1 d . . . . .
C27 C 0.2044(3) 0.8089(10) 0.3538(3) 0.0312(12) Uani 1 1 d . . . . .
H27 H 0.223(3) 0.967(10) 0.366(3) 0.047 Uiso 1 1 d . U . . .
C28 C 0.2591(3) 0.7166(10) 0.3034(3) 0.0317(12) Uani 1 1 d . . . . .
H28 H 0.241(3) 0.564(10) 0.284(3) 0.047 Uiso 1 1 d . U . . .
O29 O 0.33637(18) 0.7191(6) 0.3452(2) 0.0385(9) Uani 1 1 d D . . . .
O30 O 0.3284(2) 0.3504(8) 0.3797(2) 0.0589(12) Uani 1 1 d D . . . .
C31 C 0.3633(3) 0.5252(11) 0.3804(3) 0.0434(14) Uani 1 1 d D . . . .
C32 C 0.4436(3) 0.5590(14) 0.4218(4) 0.073(2) Uani 1 1 d D . . . .
H32A H 0.468816 0.410621 0.430924 0.110 Uiso 1 1 calc R U . . .
H32B H 0.441858 0.634520 0.469928 0.110 Uiso 1 1 calc R U . . .
H32C H 0.472289 0.653905 0.391518 0.110 Uiso 1 1 calc R U . . .
C33 C 0.2590(3) 0.8742(10) 0.2370(3) 0.0354(12) Uani 1 1 d . . . . .
H33A H 0.296205 0.816349 0.206256 0.042 Uiso 1 1 calc R U . . .
H33B H 0.276488 1.026927 0.255880 0.042 Uiso 1 1 calc R U . . .
C34 C 0.1808(3) 0.8981(9) 0.1868(3) 0.0341(12) Uani 1 1 d . . . . .
O35 O 0.1825(3) 1.0725(7) 0.1323(2) 0.0545(12) Uani 1 1 d . . . . .
H35 H 0.221(4) 1.154(13) 0.146(4) 0.082 Uiso 1 1 d . U . . .
C36 C 0.1207(3) 0.9573(10) 0.2360(3) 0.0440(15) Uani 1 1 d . . . . .
O37 O 0.0736(3) 1.1053(9) 0.2184(3) 0.0872(18) Uani 1 1 d . . . . .
C38 C 0.1228(3) 0.8206(11) 0.3066(3) 0.0418(15) Uani 1 1 d . . . . .
H38A H 0.104584 0.663951 0.293252 0.050 Uiso 1 1 calc R U . . .
H38B H 0.087496 0.889803 0.337386 0.050 Uiso 1 1 calc R U . . .
C39 C 0.1557(3) 0.6769(9) 0.1425(3) 0.0326(12) Uani 1 1 d . . . . .
H39 H 0.160851 0.543059 0.177314 0.039 Uiso 1 1 calc R U . . .
C40 C 0.0752(3) 0.6842(12) 0.0958(3) 0.0470(15) Uani 1 1 d . . . . .
H40A H 0.053640 0.528566 0.088457 0.056 Uiso 1 1 calc R U . D 1
H40B H 0.040722 0.778247 0.121094 0.056 Uiso 1 1 calc R U . D 1
C41 C 0.0845(5) 0.789(3) 0.0213(6) 0.049(3) Uani 0.77(3) 1 d . U P E 1
H41A H 0.079178 0.956428 0.022792 0.059 Uiso 0.77(3) 1 calc R U P E 1
H41B H 0.045709 0.727507 -0.019747 0.059 Uiso 0.77(3) 1 calc R U P E 1
C41B C 0.0850(18) 0.650(10) 0.0137(18) 0.047(9) Uani 0.23(3) 1 d . U P E 2
H41C H 0.077134 0.488485 -0.001142 0.056 Uiso 0.23(3) 1 calc R U P E 2
H41D H 0.047845 0.744908 -0.020107 0.056 Uiso 0.23(3) 1 calc R U P E 2
C42 C 0.1649(3) 0.7223(11) 0.0098(3) 0.0408(13) Uani 1 1 d . . . . .
H42A H 0.162887 0.599492 -0.028104 0.049 Uiso 1 1 calc R U . E 1
H42B H 0.192027 0.855055 -0.007046 0.049 Uiso 1 1 calc R U . E 1
N43 N 0.2030(2) 0.6431(7) 0.0834(2) 0.0346(10) Uani 1 1 d . . . . .
C44 C 0.2681(3) 0.5212(9) 0.0937(3) 0.0336(12) Uani 1 1 d . . . . .
O45 O 0.2943(2) 0.4211(7) 0.1523(2) 0.0437(9) Uani 1 1 d . . . . .
O46 O 0.3004(2) 0.5278(7) 0.0316(2) 0.0434(9) Uani 1 1 d . . . . .
C47 C 0.3736(3) 0.4102(11) 0.0274(3) 0.0465(15) Uani 1 1 d . . . . .
C48 C 0.3860(4) 0.4732(12) -0.0514(4) 0.067(2) Uani 1 1 d . . . . .
H48A H 0.432778 0.399944 -0.061933 0.100 Uiso 1 1 calc R U . . .
H48B H 0.390981 0.639022 -0.055090 0.100 Uiso 1 1 calc R U . . .
H48C H 0.342177 0.421261 -0.088024 0.100 Uiso 1 1 calc R U . . .
C49 C 0.3625(4) 0.1532(11) 0.0350(5) 0.068(2) Uani 1 1 d . . . . .
H49A H 0.409916 0.073916 0.029366 0.102 Uiso 1 1 calc R U . . .
H49B H 0.320864 0.101438 -0.004073 0.102 Uiso 1 1 calc R U . . .
H49C H 0.349660 0.119537 0.084619 0.102 Uiso 1 1 calc R U . . .
C50 C 0.4363(3) 0.5069(12) 0.0860(4) 0.0615(19) Uani 1 1 d . . . . .
H50A H 0.485582 0.440679 0.079622 0.092 Uiso 1 1 calc R U . . .
H50B H 0.425746 0.470076 0.136280 0.092 Uiso 1 1 calc R U . . .
H50C H 0.438255 0.672836 0.080258 0.092 Uiso 1 1 calc R U . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C2 O3 121.3(5) . . ?
O1 C2 C26 130.0(5) . . ?
O3 C2 C26 108.7(4) . . ?
C2 O3 C4 109.7(4) . . ?
O3 C4 C25 103.2(4) . . ?
O3 C4 C17 111.2(4) . . ?
C25 C4 C17 108.5(4) . . ?
O3 C4 C5 107.1(4) . . ?
C25 C4 C5 113.8(4) . . ?
C17 C4 C5 112.8(4) . . ?
N9 C5 C6 103.1(4) . . ?
N9 C5 C4 110.6(4) . . ?
C6 C5 C4 114.6(4) . . ?
N9 C5 H5 108(3) . . ?
C6 C5 H5 112(3) . . ?
C4 C5 H5 108(3) . . ?
C7B C6 C5 106.0(7) . . ?
C5 C6 C7 106.5(6) . . ?
C5 C6 H6A 110.4 . . ?
C7 C6 H6A 110.4 . . ?
C5 C6 H6B 110.4 . . ?
C7 C6 H6B 110.4 . . ?
H6A C6 H6B 108.6 . . ?
C8 C7 C6 104.1(9) . . ?
C8 C7 H7A 110.9 . . ?
C6 C7 H7A 110.9 . . ?
C8 C7 H7B 110.9 . . ?
C6 C7 H7B 110.9 . . ?
H7A C7 H7B 109.0 . . ?
C6 C7B C8 109.2(11) . . ?
C6 C7B H7C 109.8 . . ?
C8 C7B H7C 109.8 . . ?
C6 C7B H7D 109.8 . . ?
C8 C7B H7D 109.8 . . ?
H7C C7B H7D 108.3 . . ?
N9 C8 C7 103.9(7) . . ?
N9 C8 C7B 102.8(7) . . ?
N9 C8 H8A 111.0 . . ?
C7 C8 H8A 111.0 . . ?
N9 C8 H8B 111.0 . . ?
C7 C8 H8B 111.0 . . ?
H8A C8 H8B 109.0 . . ?
C10 N9 C5 121.9(5) . . ?
C10 N9 C8 122.3(4) . . ?
C5 N9 C8 112.0(4) . . ?
O11 C10 O12 125.9(5) . . ?
O11 C10 N9 124.3(5) . . ?
O12 C10 N9 109.8(5) . . ?
C10 O12 C13 121.3(4) . . ?
O12 C13 C15 109.1(4) . . ?
O12 C13 C16 101.4(4) . . ?
C15 C13 C16 111.8(5) . . ?
O12 C13 C14 110.2(4) . . ?
C15 C13 C14 112.8(5) . . ?
C16 C13 C14 111.0(5) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C4 C17 C18 108.9(4) . . ?
C4 C17 H17A 109.9 . . ?
C18 C17 H17A 109.9 . . ?
C4 C17 H17B 109.9 . . ?
C18 C17 H17B 109.9 . . ?
H17A C17 H17B 108.3 . . ?
O19B C18 C23 109(4) . . ?
C23 C18 O19 109.5(15) . . ?
O19B C18 C17 108(3) . . ?
C23 C18 C17 113.5(4) . . ?
O19 C18 C17 105.4(10) . . ?
O19B C18 H18 108(4) . . ?
C23 C18 H18 108(3) . . ?
O19 C18 H18 110(3) . . ?
C17 C18 H18 111(3) . . ?
C21 O19 C18 114.0(13) . . ?
O20 C21 O19 123.8(11) . . ?
O20 C21 C22 125.7(11) . . ?
O19 C21 C22 110.6(11) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C18 O19B C21B 121(4) . . ?
O20B C21B O19B 123(3) . . ?
O20B C21B C22B 126(3) . . ?
O19B C21B C22B 111(2) . . ?
C21B C22B H22D 109.5 . . ?
C21B C22B H22E 109.5 . . ?
H22D C22B H22E 109.5 . . ?
C21B C22B H22F 109.5 . . ?
H22D C22B H22F 109.5 . . ?
H22E C22B H22F 109.5 . . ?
C24 C23 C18 123.2(5) . . ?
C24 C23 H23 118.4 . . ?
C18 C23 H23 118.4 . . ?
C23 C24 C25 119.5(5) . . ?
C23 C24 H24 120.2 . . ?
C25 C24 H24 120.2 . . ?
C26 C25 C24 131.9(5) . . ?
C26 C25 C4 110.6(4) . . ?
C24 C25 C4 117.0(4) . . ?
C25 C26 C2 107.5(4) . . ?
C25 C26 C27 128.4(5) . . ?
C2 C26 C27 123.9(4) . . ?
C26 C27 C28 114.1(4) . . ?
C26 C27 C38 111.8(4) . . ?
C28 C27 C38 108.2(4) . . ?
C26 C27 H27 109(3) . . ?
C28 C27 H27 105(3) . . ?
C38 C27 H27 109(3) . . ?
O29 C28 C33 106.4(4) . . ?
O29 C28 C27 108.8(4) . . ?
C33 C28 C27 109.7(4) . . ?
O29 C28 H28 115(3) . . ?
C33 C28 H28 108(3) . . ?
C27 C28 H28 109(3) . . ?
C31 O29 C28 117.7(4) . . ?
O30 C31 O29 125.1(5) . . ?
O30 C31 C32 124.2(6) . . ?
O29 C31 C32 110.7(6) . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C28 C33 C34 114.0(4) . . ?
C28 C33 H33A 108.8 . . ?
C34 C33 H33A 108.8 . . ?
C28 C33 H33B 108.8 . . ?
C34 C33 H33B 108.8 . . ?
H33A C33 H33B 107.7 . . ?
O35 C34 C33 110.7(4) . . ?
O35 C34 C36 109.5(4) . . ?
C33 C34 C36 108.9(4) . . ?
O35 C34 C39 106.5(4) . . ?
C33 C34 C39 112.4(4) . . ?
C36 C34 C39 108.7(4) . . ?
C34 O35 H35 108(5) . . ?
O37 C36 C38 121.7(5) . . ?
O37 C36 C34 121.6(5) . . ?
C38 C36 C34 116.7(4) . . ?
C36 C38 C27 112.2(4) . . ?
C36 C38 H38A 109.2 . . ?
C27 C38 H38A 109.2 . . ?
C36 C38 H38B 109.2 . . ?
C27 C38 H38B 109.2 . . ?
H38A C38 H38B 107.9 . . ?
N43 C39 C40 101.2(4) . . ?
N43 C39 C34 109.7(4) . . ?
C40 C39 C34 114.9(4) . . ?
N43 C39 H39 110.2 . . ?
C40 C39 H39 110.2 . . ?
C34 C39 H39 110.2 . . ?
C41 C40 C39 105.7(5) . . ?
C39 C40 C41B 106.4(13) . . ?
C41 C40 H40A 110.6 . . ?
C39 C40 H40A 110.6 . . ?
C41 C40 H40B 110.6 . . ?
C39 C40 H40B 110.6 . . ?
H40A C40 H40B 108.7 . . ?
C40 C41 C42 105.1(7) . . ?
C40 C41 H41A 110.7 . . ?
C42 C41 H41A 110.7 . . ?
C40 C41 H41B 110.7 . . ?
C42 C41 H41B 110.7 . . ?
H41A C41 H41B 108.8 . . ?
C42 C41B C40 106(2) . . ?
C42 C41B H41C 110.6 . . ?
C40 C41B H41C 110.6 . . ?
C42 C41B H41D 110.6 . . ?
C40 C41B H41D 110.6 . . ?
H41C C41B H41D 108.7 . . ?
N43 C42 C41B 99.5(15) . . ?
N43 C42 C41 105.0(5) . . ?
N43 C42 H42A 110.8 . . ?
C41 C42 H42A 110.8 . . ?
N43 C42 H42B 110.8 . . ?
C41 C42 H42B 110.8 . . ?
H42A C42 H42B 108.8 . . ?
C44 N43 C42 123.4(4) . . ?
C44 N43 C39 123.3(4) . . ?
C42 N43 C39 112.5(4) . . ?
O45 C44 O46 125.3(5) . . ?
O45 C44 N43 124.4(5) . . ?
O46 C44 N43 110.2(4) . . ?
C44 O46 C47 121.9(4) . . ?
O46 C47 C50 109.7(5) . . ?
O46 C47 C48 101.5(5) . . ?
C50 C47 C48 111.1(5) . . ?
O46 C47 C49 109.2(5) . . ?
C50 C47 C49 113.5(6) . . ?
C48 C47 C49 111.4(6) . . ?
C47 C48 H48A 109.5 . . ?
C47 C48 H48B 109.5 . . ?
H48A C48 H48B 109.5 . . ?
C47 C48 H48C 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
C47 C49 H49A 109.5 . . ?
C47 C49 H49B 109.5 . . ?
H49A C49 H49B 109.5 . . ?
C47 C49 H49C 109.5 . . ?
H49A C49 H49C 109.5 . . ?
H49B C49 H49C 109.5 . . ?
C47 C50 H50A 109.5 . . ?
C47 C50 H50B 109.5 . . ?
H50A C50 H50B 109.5 . . ?
C47 C50 H50C 109.5 . . ?
H50A C50 H50C 109.5 . . ?
H50B C50 H50C 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
O1 C2 1.197(6) . ?
C2 O3 1.370(6) . ?
C2 C26 1.480(7) . ?
O3 C4 1.454(6) . ?
C4 C25 1.504(7) . ?
C4 C17 1.519(7) . ?
C4 C5 1.559(7) . ?
C5 N9 1.461(6) . ?
C5 C6 1.535(7) . ?
C5 H5 1.11(6) . ?
C6 C7B 1.411(16) . ?
C6 C7 1.549(15) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.475(16) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7B C8 1.514(19) . ?
C7B H7C 0.9900 . ?
C7B H7D 0.9900 . ?
C8 N9 1.467(6) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
N9 C10 1.366(6) . ?
C10 O11 1.205(6) . ?
C10 O12 1.349(6) . ?
O12 C13 1.481(6) . ?
C13 C15 1.504(8) . ?
C13 C16 1.517(8) . ?
C13 C14 1.525(8) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.522(7) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 O19B 1.34(5) . ?
C18 C23 1.493(8) . ?
C18 O19 1.503(19) . ?
C18 H18 1.05(6) . ?
O19 C21 1.364(15) . ?
O20 C21 1.190(11) . ?
C21 C22 1.494(12) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
O19B C21B 1.36(2) . ?
O20B C21B 1.188(19) . ?
C21B C22B 1.50(2) . ?
C22B H22D 0.9800 . ?
C22B H22E 0.9800 . ?
C22B H22F 0.9800 . ?
C23 C24 1.345(7) . ?
C23 H23 0.9500 . ?
C24 C25 1.454(7) . ?
C24 H24 0.9500 . ?
C25 C26 1.332(7) . ?
C26 C27 1.494(7) . ?
C27 C28 1.533(7) . ?
C27 C38 1.553(7) . ?
C27 H27 0.99(6) . ?
C28 O29 1.449(6) . ?
C28 C33 1.513(7) . ?
C28 H28 1.00(6) . ?
O29 C31 1.350(7) . ?
O30 C31 1.197(7) . ?
C31 C32 1.504(8) . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33 C34 1.530(7) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 O35 1.422(6) . ?
C34 C36 1.537(7) . ?
C34 C39 1.549(7) . ?
O35 H35 0.83(7) . ?
C36 O37 1.209(6) . ?
C36 C38 1.501(8) . ?
C38 H38A 0.9900 . ?
C38 H38B 0.9900 . ?
C39 N43 1.476(6) . ?
C39 C40 1.531(7) . ?
C39 H39 1.0000 . ?
C40 C41 1.511(11) . ?
C40 C41B 1.53(3) . ?
C40 H40A 0.9900 . ?
C40 H40B 0.9900 . ?
C41 C42 1.522(11) . ?
C41 H41A 0.9900 . ?
C41 H41B 0.9900 . ?
C41B C42 1.49(3) . ?
C41B H41C 0.9900 . ?
C41B H41D 0.9900 . ?
C42 N43 1.461(6) . ?
C42 H42A 0.9900 . ?
C42 H42B 0.9900 . ?
N43 C44 1.343(6) . ?
C44 O45 1.232(6) . ?
C44 O46 1.342(6) . ?
O46 C47 1.481(6) . ?
C47 C50 1.511(8) . ?
C47 C48 1.521(8) . ?
C47 C49 1.529(9) . ?
C48 H48A 0.9800 . ?
C48 H48B 0.9800 . ?
C48 H48C 0.9800 . ?
C49 H49A 0.9800 . ?
C49 H49B 0.9800 . ?
C49 H49C 0.9800 . ?
C50 H50A 0.9800 . ?
C50 H50B 0.9800 . ?
C50 H50C 0.9800 . ?
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
_geom_hbond_publ_flag
O35 H35 O45 0.83(7) 2.03(8) 2.828(5) 161(7) 1_565 yes
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
O1 C2 O3 C4 -178.0(5) . . . . ?
C26 C2 O3 C4 2.8(5) . . . . ?
C2 O3 C4 C25 -5.6(5) . . . . ?
C2 O3 C4 C17 -121.7(4) . . . . ?
C2 O3 C4 C5 114.7(4) . . . . ?
O3 C4 C5 N9 50.2(5) . . . . ?
C25 C4 C5 N9 163.5(4) . . . . ?
C17 C4 C5 N9 -72.4(6) . . . . ?
O3 C4 C5 C6 -65.8(6) . . . . ?
C25 C4 C5 C6 47.5(6) . . . . ?
C17 C4 C5 C6 171.5(5) . . . . ?
N9 C5 C6 C7B -24.0(13) . . . . ?
C4 C5 C6 C7B 96.2(13) . . . . ?
N9 C5 C6 C7 8.0(11) . . . . ?
C4 C5 C6 C7 128.3(11) . . . . ?
C5 C6 C7 C8 -25.1(16) . . . . ?
C5 C6 C7B C8 27.0(19) . . . . ?
C6 C7 C8 N9 31.9(15) . . . . ?
C6 C7B C8 N9 -18.8(18) . . . . ?
C6 C5 N9 C10 -146.1(5) . . . . ?
C4 C5 N9 C10 91.0(6) . . . . ?
C6 C5 N9 C8 12.6(6) . . . . ?
C4 C5 N9 C8 -110.4(5) . . . . ?
C7 C8 N9 C10 129.6(11) . . . . ?
C7B C8 N9 C10 161.2(11) . . . . ?
C7 C8 N9 C5 -29.0(11) . . . . ?
C7B C8 N9 C5 2.7(12) . . . . ?
C5 N9 C10 O11 -3.1(8) . . . . ?
C8 N9 C10 O11 -159.5(6) . . . . ?
C5 N9 C10 O12 178.3(4) . . . . ?
C8 N9 C10 O12 21.8(7) . . . . ?
O11 C10 O12 C13 13.6(8) . . . . ?
N9 C10 O12 C13 -167.8(4) . . . . ?
C10 O12 C13 C15 59.0(6) . . . . ?
C10 O12 C13 C16 177.0(5) . . . . ?
C10 O12 C13 C14 -65.4(6) . . . . ?
O3 C4 C17 C18 173.6(4) . . . . ?
C25 C4 C17 C18 60.8(5) . . . . ?
C5 C4 C17 C18 -66.1(6) . . . . ?
C4 C17 C18 O19B -167(3) . . . . ?
C4 C17 C18 C23 -46.0(6) . . . . ?
C4 C17 C18 O19 -165.9(13) . . . . ?
C23 C18 O19 C21 80(2) . . . . ?
C17 C18 O19 C21 -158(2) . . . . ?
C18 O19 C21 O20 -6(4) . . . . ?
C18 O19 C21 C22 174.0(18) . . . . ?
C23 C18 O19B C21B 105(7) . . . . ?
C17 C18 O19B C21B -131(6) . . . . ?
C18 O19B C21B O20B -9(10) . . . . ?
C18 O19B C21B C22B 167(6) . . . . ?
O19B C18 C23 C24 136.1(17) . . . . ?
O19 C18 C23 C24 133.7(8) . . . . ?
C17 C18 C23 C24 16.2(7) . . . . ?
C18 C23 C24 C25 -0.9(8) . . . . ?
C23 C24 C25 C26 -153.3(5) . . . . ?
C23 C24 C25 C4 17.6(7) . . . . ?
O3 C4 C25 C26 6.9(5) . . . . ?
C17 C4 C25 C26 124.9(4) . . . . ?
C5 C4 C25 C26 -108.8(5) . . . . ?
O3 C4 C25 C24 -166.0(4) . . . . ?
C17 C4 C25 C24 -47.9(5) . . . . ?
C5 C4 C25 C24 78.4(5) . . . . ?
C24 C25 C26 C2 166.0(5) . . . . ?
C4 C25 C26 C2 -5.4(5) . . . . ?
C24 C25 C26 C27 -8.5(9) . . . . ?
C4 C25 C26 C27 -179.9(4) . . . . ?
O1 C2 C26 C25 -177.4(5) . . . . ?
O3 C2 C26 C25 1.7(5) . . . . ?
O1 C2 C26 C27 -2.5(8) . . . . ?
O3 C2 C26 C27 176.5(4) . . . . ?
C25 C26 C27 C28 100.4(6) . . . . ?
C2 C26 C27 C28 -73.3(6) . . . . ?
C25 C26 C27 C38 -136.3(5) . . . . ?
C2 C26 C27 C38 49.9(6) . . . . ?
C26 C27 C28 O29 -58.7(6) . . . . ?
C38 C27 C28 O29 176.2(4) . . . . ?
C26 C27 C28 C33 -174.6(4) . . . . ?
C38 C27 C28 C33 60.3(6) . . . . ?
C33 C28 O29 C31 -146.6(5) . . . . ?
C27 C28 O29 C31 95.3(5) . . . . ?
C28 O29 C31 O30 0.1(8) . . . . ?
C28 O29 C31 C32 -179.2(5) . . . . ?
O29 C28 C33 C34 -178.6(4) . . . . ?
C27 C28 C33 C34 -61.1(6) . . . . ?
C28 C33 C34 O35 171.6(4) . . . . ?
C28 C33 C34 C36 51.1(6) . . . . ?
C28 C33 C34 C39 -69.5(6) . . . . ?
O35 C34 C36 O37 13.7(7) . . . . ?
C33 C34 C36 O37 134.9(6) . . . . ?
C39 C34 C36 O37 -102.3(6) . . . . ?
O35 C34 C36 C38 -167.0(4) . . . . ?
C33 C34 C36 C38 -45.8(6) . . . . ?
C39 C34 C36 C38 77.1(5) . . . . ?
O37 C36 C38 C27 -130.9(6) . . . . ?
C34 C36 C38 C27 49.7(6) . . . . ?
C26 C27 C38 C36 178.5(4) . . . . ?
C28 C27 C38 C36 -55.0(6) . . . . ?
O35 C34 C39 N43 50.1(5) . . . . ?
C33 C34 C39 N43 -71.3(5) . . . . ?
C36 C34 C39 N43 168.0(4) . . . . ?
O35 C34 C39 C40 -63.1(6) . . . . ?
C33 C34 C39 C40 175.6(4) . . . . ?
C36 C34 C39 C40 54.8(6) . . . . ?
N43 C39 C40 C41 -32.0(9) . . . . ?
C34 C39 C40 C41 86.1(9) . . . . ?
N43 C39 C40 C41B 1(2) . . . . ?
C34 C39 C40 C41B 119(2) . . . . ?
C39 C40 C41 C42 29.5(12) . . . . ?
C39 C40 C41B C42 -23(4) . . . . ?
C40 C41B C42 N43 36(3) . . . . ?
C40 C41 C42 N43 -14.7(12) . . . . ?
C41B C42 N43 C44 132(2) . . . . ?
C41 C42 N43 C44 164.1(8) . . . . ?
C41B C42 N43 C39 -38(2) . . . . ?
C41 C42 N43 C39 -6.1(9) . . . . ?
C40 C39 N43 C44 -146.5(5) . . . . ?
C34 C39 N43 C44 91.8(6) . . . . ?
C40 C39 N43 C42 23.7(6) . . . . ?
C34 C39 N43 C42 -98.1(5) . . . . ?
C42 N43 C44 O45 -167.4(5) . . . . ?
C39 N43 C44 O45 1.7(8) . . . . ?
C42 N43 C44 O46 13.6(7) . . . . ?
C39 N43 C44 O46 -177.3(4) . . . . ?
O45 C44 O46 C47 0.2(8) . . . . ?
N43 C44 O46 C47 179.2(4) . . . . ?
C44 O46 C47 C50 -61.2(7) . . . . ?
C44 O46 C47 C48 -178.7(5) . . . . ?
C44 O46 C47 C49 63.6(7) . . . . ?
