#------------------------------------------------------------------------------
#$Date: 2020-10-22 02:21:43 +0300 (Thu, 22 Oct 2020) $
#$Revision: 258532 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/89/4038902.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_4038902
loop_
_publ_author_name
'Zheng, Kuan'
'Shen, Defeng'
'Zhang, Bingbing'
'Hong, Ran'
_publ_section_title
;
 The Landscape of Lankacidin Biomimetic Synthesis: Structural Revisions
 and Biogenetic Implications.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c01930
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H35 N O5'
_chemical_formula_sum            'C24 H35 N O5'
_chemical_formula_weight         417.53
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 108.2940(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.1817(4)
_cell_length_b                   5.89350(10)
_cell_length_c                   21.8822(5)
_cell_measurement_reflns_used    7730
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      68.17
_cell_measurement_theta_min      4.26
_cell_volume                     2471.14(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0451
_diffrn_reflns_av_unetI/netI     0.0348
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            15700
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.388
_diffrn_reflns_theta_min         2.126
_exptl_absorpt_coefficient_mu    0.627
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6174
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.122
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Flack x determined using 1406 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.17(11)
_refine_ls_extinction_coef       0.0024(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         4510
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0634
_refine_ls_R_factor_gt           0.0515
_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)+(0.0762P)²+0.9658P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1373
_refine_ls_wR_factor_ref         0.1538
_reflns_Friedel_coverage         0.805
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                3728
_reflns_number_total             4510
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c01930_si_001.cif
_cod_data_source_block           571
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               4038902
_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.
;
_shelx_estimated_absorpt_t_min   0.844
_shelx_estimated_absorpt_t_max   0.952
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, 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 0.39418(18) 0.9511(5) 0.31987(15) 0.0792(9) Uani 1 1 d . . . . .
O2 O 0.49748(18) 0.6051(9) 0.07077(16) 0.1087(13) Uani 1 1 d . . . . .
H2A H 0.507683 0.739707 0.070476 0.163 Uiso 1 1 calc R U . . .
O3 O 0.03381(15) 0.5830(10) 0.06938(16) 0.1181(16) Uani 1 1 d . . . . .
H3A H 0.014749 0.459186 0.067634 0.177 Uiso 1 1 calc R U . . .
O4 O 0.3218(2) 0.5374(5) 0.47498(17) 0.0945(11) Uani 1 1 d . . . . .
O5 O 0.3550(3) -0.0366(6) 0.4584(2) 0.141(2) Uani 1 1 d . . . . .
H5A H 0.340523 -0.158598 0.466979 0.211 Uiso 1 1 calc R U . . .
N1 N 0.34867(17) 0.3382(5) 0.39793(13) 0.0562(7) Uani 1 1 d . . . . .
H1A H 0.359498 0.205970 0.387397 0.067 Uiso 1 1 calc R U . . .
C1 C 0.4252(2) 0.7810(6) 0.31214(17) 0.0583(9) Uani 1 1 d . . . . .
C2 C 0.4704(2) 0.7948(7) 0.26968(19) 0.0650(10) Uani 1 1 d . . . . .
C3 C 0.4779(2) 0.6215(7) 0.23487(19) 0.0663(9) Uani 1 1 d . . . . .
H3B H 0.459219 0.484225 0.242586 0.080 Uiso 1 1 calc R U . . .
C4 C 0.5133(2) 0.6204(9) 0.18393(19) 0.0728(11) Uani 1 1 d . . . . .
H4A H 0.550117 0.507505 0.194790 0.087 Uiso 1 1 calc R U . . .
H4B H 0.534591 0.767370 0.183058 0.087 Uiso 1 1 calc R U . . .
C5 C 0.4628(2) 0.5686(9) 0.1174(2) 0.0748(12) Uani 1 1 d . . . . .
H5B H 0.449897 0.407943 0.116138 0.090 Uiso 1 1 calc R U . . .
C6 C 0.3980(2) 0.7068(7) 0.10468(19) 0.0669(10) Uani 1 1 d . . . . .
H6A H 0.402553 0.862255 0.112183 0.080 Uiso 1 1 calc R U . . .
C7 C 0.33441(19) 0.6206(7) 0.08334(17) 0.0607(9) Uani 1 1 d . . . . .
H7A H 0.331727 0.468983 0.071011 0.073 Uiso 1 1 calc R U . . .
C8 C 0.2679(2) 0.7317(6) 0.07655(18) 0.0599(9) Uani 1 1 d . . . . .
C9 C 0.2095(2) 0.6184(8) 0.04792(17) 0.0639(9) Uani 1 1 d . . . . .
H9A H 0.215412 0.479008 0.030398 0.077 Uiso 1 1 calc R U . . .
C10 C 0.1358(2) 0.6834(9) 0.03992(19) 0.0710(11) Uani 1 1 d . . . . .
H10A H 0.106881 0.651675 -0.003812 0.085 Uiso 1 1 calc R U . . .
H10B H 0.133303 0.844830 0.047560 0.085 Uiso 1 1 calc R U . . .
C11 C 0.10875(19) 0.5514(10) 0.08691(18) 0.0742(12) Uani 1 1 d . . . . .
H11A H 0.118513 0.389860 0.083508 0.089 Uiso 1 1 calc R U . . .
C12 C 0.1433(2) 0.6266(10) 0.15421(18) 0.0739(12) Uani 1 1 d . . . . .
H12A H 0.126427 0.756557 0.168356 0.089 Uiso 1 1 calc R U . . .
C13 C 0.1965(2) 0.5202(8) 0.19526(17) 0.0651(9) Uani 1 1 d . . . . .
H13A H 0.208692 0.381071 0.181779 0.078 Uiso 1 1 calc R U . . .
C14 C 0.2384(2) 0.5956(7) 0.25929(17) 0.0609(9) Uani 1 1 d . . . . .
C15 C 0.2961(2) 0.4779(7) 0.28980(16) 0.0584(9) Uani 1 1 d . . . . .
H15A H 0.304682 0.349914 0.268592 0.070 Uiso 1 1 calc R U . . .
C16 C 0.34864(19) 0.5281(6) 0.35435(15) 0.0535(8) Uani 1 1 d . . . . .
H16A H 0.334446 0.666478 0.371745 0.064 Uiso 1 1 calc R U . . .
C17 C 0.4215(2) 0.5649(6) 0.34814(16) 0.0573(9) Uani 1 1 d . . . . .
H17A H 0.433361 0.435680 0.325371 0.069 Uiso 1 1 calc R U . . .
C18 C 0.3333(2) 0.3562(6) 0.45208(18) 0.0604(9) Uani 1 1 d . . . . .
C19 C 0.3287(2) 0.1374(6) 0.48654(18) 0.0670(10) Uani 1 1 d . . . . .
H19A H 0.279306 0.105666 0.480071 0.080 Uiso 1 1 calc R U . . .
C20 C 0.3648(5) 0.1512(11) 0.5565(3) 0.133(3) Uani 1 1 d . . . . .
H20A H 0.345374 0.273212 0.574462 0.200 Uiso 1 1 calc R U . . .
H20B H 0.358923 0.010976 0.576516 0.200 Uiso 1 1 calc R U . . .
H20C H 0.413637 0.178548 0.564070 0.200 Uiso 1 1 calc R U . . .
C21 C 0.4992(5) 1.0245(10) 0.2657(4) 0.142(3) Uani 1 1 d . . . . .
H21A H 0.487476 1.124341 0.295339 0.213 Uiso 1 1 calc R U . . .
H21B H 0.549080 1.015094 0.276341 0.213 Uiso 1 1 calc R U . . .
H21C H 0.479824 1.082194 0.222705 0.213 Uiso 1 1 calc R U . . .
C22 C 0.2704(3) 0.9643(8) 0.1059(2) 0.0819(12) Uani 1 1 d . . . . .
H22A H 0.318049 1.011783 0.123728 0.123 Uiso 1 1 calc R U . . .
H22B H 0.245646 1.069931 0.073315 0.123 Uiso 1 1 calc R U . . .
H22C H 0.248934 0.959120 0.139333 0.123 Uiso 1 1 calc R U . . .
C23 C 0.2161(3) 0.8087(10) 0.2862(2) 0.0915(16) Uani 1 1 d . . . . .
H23A H 0.173447 0.864520 0.256391 0.137 Uiso 1 1 calc R U . . .
H23B H 0.208891 0.774643 0.326512 0.137 Uiso 1 1 calc R U . . .
H23C H 0.251813 0.922016 0.292630 0.137 Uiso 1 1 calc R U . . .
C24 C 0.4775(2) 0.5906(10) 0.4142(2) 0.0850(13) Uani 1 1 d . . . . .
H24A H 0.477799 0.457595 0.439659 0.127 Uiso 1 1 calc R U . . .
H24B H 0.522440 0.608845 0.408479 0.127 Uiso 1 1 calc R U . . .
H24C H 0.467240 0.721355 0.435833 0.127 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 0.0181 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
C5 O2 H2A 109.5 . . ?
C11 O3 H3A 109.5 . . ?
C19 O5 H5A 109.5 . . ?
C18 N1 C16 124.7(3) . . ?
C18 N1 H1A 117.7 . . ?
C16 N1 H1A 117.7 . . ?
O1 C1 C2 118.8(3) . . ?
O1 C1 C17 120.5(3) . . ?
C2 C1 C17 120.6(3) . . ?
C3 C2 C21 123.8(4) . . ?
C3 C2 C1 121.6(4) . . ?
C21 C2 C1 114.4(4) . . ?
C2 C3 C4 127.1(4) . . ?
C2 C3 H3B 116.4 . . ?
C4 C3 H3B 116.4 . . ?
C3 C4 C5 112.3(3) . . ?
C3 C4 H4A 109.1 . . ?
C5 C4 H4A 109.1 . . ?
C3 C4 H4B 109.1 . . ?
C5 C4 H4B 109.1 . . ?
H4A C4 H4B 107.9 . . ?
O2 C5 C6 112.6(4) . . ?
O2 C5 C4 108.9(3) . . ?
C6 C5 C4 110.7(3) . . ?
O2 C5 H5B 108.2 . . ?
C6 C5 H5B 108.2 . . ?
C4 C5 H5B 108.2 . . ?
C7 C6 C5 123.6(4) . . ?
C7 C6 H6A 118.2 . . ?
C5 C6 H6A 118.2 . . ?
C6 C7 C8 128.6(4) . . ?
C6 C7 H7A 115.7 . . ?
C8 C7 H7A 115.7 . . ?
C9 C8 C7 118.3(4) . . ?
C9 C8 C22 124.3(4) . . ?
C7 C8 C22 117.3(4) . . ?
C8 C9 C10 129.1(4) . . ?
C8 C9 H9A 115.5 . . ?
C10 C9 H9A 115.5 . . ?
C9 C10 C11 110.2(3) . . ?
C9 C10 H10A 109.6 . . ?
C11 C10 H10A 109.6 . . ?
C9 C10 H10B 109.6 . . ?
C11 C10 H10B 109.6 . . ?
H10A C10 H10B 108.1 . . ?
O3 C11 C12 110.5(3) . . ?
O3 C11 C10 108.8(3) . . ?
C12 C11 C10 111.2(4) . . ?
O3 C11 H11A 108.8 . . ?
C12 C11 H11A 108.8 . . ?
C10 C11 H11A 108.8 . . ?
C13 C12 C11 124.1(5) . . ?
C13 C12 H12A 117.9 . . ?
C11 C12 H12A 117.9 . . ?
C12 C13 C14 127.6(4) . . ?
C12 C13 H13A 116.2 . . ?
C14 C13 H13A 116.2 . . ?
C15 C14 C13 118.1(4) . . ?
C15 C14 C23 123.6(4) . . ?
C13 C14 C23 118.2(4) . . ?
C14 C15 C16 127.7(3) . . ?
C14 C15 H15A 116.1 . . ?
C16 C15 H15A 116.1 . . ?
N1 C16 C15 108.4(3) . . ?
N1 C16 C17 111.1(3) . . ?
C15 C16 C17 110.9(3) . . ?
N1 C16 H16A 108.8 . . ?
C15 C16 H16A 108.8 . . ?
C17 C16 H16A 108.8 . . ?
C1 C17 C16 111.8(3) . . ?
C1 C17 C24 105.4(3) . . ?
C16 C17 C24 111.9(3) . . ?
C1 C17 H17A 109.2 . . ?
C16 C17 H17A 109.2 . . ?
C24 C17 H17A 109.2 . . ?
O4 C18 N1 124.2(3) . . ?
O4 C18 C19 119.2(3) . . ?
N1 C18 C19 116.6(3) . . ?
O5 C19 C20 111.7(5) . . ?
O5 C19 C18 108.5(3) . . ?
C20 C19 C18 112.5(4) . . ?
O5 C19 H19A 108.0 . . ?
C20 C19 H19A 108.0 . . ?
C18 C19 H19A 108.0 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C2 C21 H21A 109.5 . . ?
C2 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C2 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C8 C22 H22A 109.5 . . ?
C8 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C8 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C14 C23 H23A 109.5 . . ?
C14 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C14 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C17 C24 H24A 109.5 . . ?
C17 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C17 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 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 C1 1.221(5) . ?
O2 C5 1.423(5) . ?
O2 H2A 0.8200 . ?
O3 C11 1.451(5) . ?
O3 H3A 0.8200 . ?
O4 C18 1.232(4) . ?
O5 C19 1.385(5) . ?
O5 H5A 0.8200 . ?
N1 C18 1.321(4) . ?
N1 C16 1.470(4) . ?
N1 H1A 0.8600 . ?
C1 C2 1.494(6) . ?
C1 C17 1.512(5) . ?
C2 C3 1.311(6) . ?
C2 C21 1.487(7) . ?
C3 C4 1.501(5) . ?
C3 H3B 0.9300 . ?
C4 C5 1.523(6) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.492(6) . ?
C5 H5B 0.9800 . ?
C6 C7 1.322(6) . ?
C6 H6A 0.9300 . ?
C7 C8 1.459(6) . ?
C7 H7A 0.9300 . ?
C8 C9 1.327(6) . ?
C8 C22 1.508(6) . ?
C9 C10 1.492(6) . ?
C9 H9A 0.9300 . ?
C10 C11 1.521(6) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.485(6) . ?
C11 H11A 0.9800 . ?
C12 C13 1.322(6) . ?
C12 H12A 0.9300 . ?
C13 C14 1.460(6) . ?
C13 H13A 0.9300 . ?
C14 C15 1.339(5) . ?
C14 C23 1.514(6) . ?
C15 C16 1.506(5) . ?
C15 H15A 0.9300 . ?
C16 C17 1.534(5) . ?
C16 H16A 0.9800 . ?
C17 C24 1.538(6) . ?
C17 H17A 0.9800 . ?
C18 C19 1.511(5) . ?
C19 C20 1.477(7) . ?
C19 H19A 0.9800 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
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
O2 H2A O3 0.82 2.09 2.913(8) 179.8 3 yes
O3 H3A O2 0.82 2.12 2.913(8) 162.5 3_445 yes
O5 H5A O4 0.82 1.85 2.653(5) 165.6 1_545 yes
N1 H1A O1 0.86 2.36 3.155(4) 153.4 1_545 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 C1 C2 C3 -146.9(4) . . . . ?
C17 C1 C2 C3 36.9(6) . . . . ?
O1 C1 C2 C21 27.2(7) . . . . ?
C17 C1 C2 C21 -149.0(5) . . . . ?
C21 C2 C3 C4 -2.5(8) . . . . ?
C1 C2 C3 C4 171.1(4) . . . . ?
C2 C3 C4 C5 -115.5(5) . . . . ?
C3 C4 C5 O2 171.0(4) . . . . ?
C3 C4 C5 C6 46.9(5) . . . . ?
O2 C5 C6 C7 107.7(5) . . . . ?
C4 C5 C6 C7 -130.2(4) . . . . ?
C5 C6 C7 C8 171.8(4) . . . . ?
C6 C7 C8 C9 173.4(4) . . . . ?
C6 C7 C8 C22 -9.8(6) . . . . ?
C7 C8 C9 C10 174.2(4) . . . . ?
C22 C8 C9 C10 -2.4(6) . . . . ?
C8 C9 C10 C11 -103.8(5) . . . . ?
C9 C10 C11 O3 -168.5(4) . . . . ?
C9 C10 C11 C12 69.6(5) . . . . ?
O3 C11 C12 C13 140.8(5) . . . . ?
C10 C11 C12 C13 -98.3(6) . . . . ?
C11 C12 C13 C14 172.4(4) . . . . ?
C12 C13 C14 C15 -171.0(4) . . . . ?
C12 C13 C14 C23 6.2(6) . . . . ?
C13 C14 C15 C16 177.3(3) . . . . ?
C23 C14 C15 C16 0.3(7) . . . . ?
C18 N1 C16 C15 -119.4(4) . . . . ?
C18 N1 C16 C17 118.5(4) . . . . ?
C14 C15 C16 N1 117.6(4) . . . . ?
C14 C15 C16 C17 -120.2(4) . . . . ?
O1 C1 C17 C16 37.8(5) . . . . ?
C2 C1 C17 C16 -146.0(3) . . . . ?
O1 C1 C17 C24 -83.9(5) . . . . ?
C2 C1 C17 C24 92.3(4) . . . . ?
N1 C16 C17 C1 -171.0(3) . . . . ?
C15 C16 C17 C1 68.3(4) . . . . ?
N1 C16 C17 C24 -53.1(4) . . . . ?
C15 C16 C17 C24 -173.8(3) . . . . ?
C16 N1 C18 O4 -5.4(7) . . . . ?
C16 N1 C18 C19 173.6(4) . . . . ?
O4 C18 C19 O5 -169.9(5) . . . . ?
N1 C18 C19 O5 11.0(6) . . . . ?
O4 C18 C19 C20 -45.8(7) . . . . ?
N1 C18 C19 C20 135.1(5) . . . . ?
