#------------------------------------------------------------------------------
#$Date: 2025-08-19 00:06:14 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301780 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/95/1559509.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_1559509
loop_
_publ_author_name
'Guo, Yong-Wei'
'Liu, Xiao-Jing'
'Yuan, Jie'
'Li, Hou-Jin'
'Mahmud, Taifo'
'Hong, Ming-Jun'
'Yu, Jian-Chen'
'Lan, Wen-Jian'
_publ_section_title
;
 l-Tryptophan Induces a Marine-Derived Fusarium sp. to Produce
 Indole Alkaloids with Activity against the Zika Virus.
;
_journal_issue                   11
_journal_name_full               'Journal of natural products'
_journal_page_first              3372
_journal_page_last               3380
_journal_paper_doi               10.1021/acs.jnatprod.0c00717
_journal_volume                  83
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C28 H37 N O4'
_chemical_formula_sum            'C28 H37 N O4'
_chemical_formula_weight         451.58
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-07-09
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.32712(4)
_cell_length_b                   17.39284(13)
_cell_length_c                   21.08445(16)
_cell_measurement_reflns_used    18313
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.7510
_cell_measurement_theta_min      3.2860
_cell_volume                     2320.27(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -61.00  26.00   0.50    0.05    --  -46.62  50.00 146.00  174
  2  ω   -173.00 -85.00   0.50    0.25    -- -100.00 -50.00   0.00  176
  3  ω     34.00 129.00   0.50    0.25    --  107.00 -72.00 170.00  190
  4  ω     50.00 160.00   0.50    0.25    --  107.00 164.00 164.00  220
  5  ω   -119.00 -71.00   0.50    0.05    --  -46.62-125.00  90.00   96
  6  ω   -119.00 -71.00   0.50    0.05    --  -46.62-125.00  60.00   96
  7  ω    -61.00  27.00   0.50    0.05    --  -46.62  38.00 -90.00  176
  8  ω   -115.00 -25.00   0.50    0.25    -- -100.00  30.00 -30.00  180
  9  ω     31.00 125.00   0.50    0.25    --  107.00 -15.00 -30.00  188
 10  ω     34.00 117.00   0.50    0.25    --  107.00-125.00-180.00  166
 11  ω     35.00 122.00   0.50    0.25    --  107.00 -45.00 120.00  174
 12  ω     76.00 178.00   0.50    0.25    --  107.00 125.00-120.00  204
 13  ω     34.00 109.00   0.50    0.25    --  107.00 -94.00-180.00  150
 14  ω     31.00 125.00   0.50    0.25    --  107.00 -15.00 150.00  188
 15  ω   -119.00 -23.00   0.50    0.05    --  -46.62 -77.00  60.00  192
 16  ω   -119.00 -68.00   0.50    0.05    --  -46.62 -57.00 -90.00  102
 17  ω   -119.00 -25.00   0.50    0.05    --  -46.62 -72.00 170.00  188
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0428865000
_diffrn_orient_matrix_UB_12      -0.0402480000
_diffrn_orient_matrix_UB_13      0.0638374000
_diffrn_orient_matrix_UB_21      -0.1435141000
_diffrn_orient_matrix_UB_22      -0.0586235000
_diffrn_orient_matrix_UB_23      -0.0338386000
_diffrn_orient_matrix_UB_31      0.1919361000
_diffrn_orient_matrix_UB_32      -0.0527832000
_diffrn_orient_matrix_UB_33      -0.0110095000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_av_unetI/netI     0.0251
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            23647
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.912
_diffrn_reflns_theta_min         3.294
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.678
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_description       needle
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.155
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details
;
 Flack x determined using 1900 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     303
_refine_ls_number_reflns         4788
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0308
_refine_ls_R_factor_gt           0.0293
_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)+(0.0411P)²+0.3698P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0752
_refine_ls_wR_factor_ref         0.0773
_reflns_Friedel_coverage         0.722
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.970
_reflns_number_gt                4615
_reflns_number_total             4788
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            np0c00717_si_001.cif
_cod_data_source_block           guoyw_181227
_cod_depositor_comments          'Adding full bibliography for 1559509.cif.'
_cod_database_code               1559509
_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_max   0.935
_shelx_estimated_absorpt_t_min   0.823
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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
2.a Ternary CH refined with riding coordinates:
 C13(H13), C16(H16), C8(H8), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B), C11(H11A,H11B), C15(H15A,H15B), C14(H14A,H14B),
 C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C27(H27), C23(H23), C20(H20), C21(H21), C22(H22)
2.d Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C26(H26A,H26B,H26C), C0AA(H0AA,H0AB,H0AC), C30(H30A,H30B,
 H30C), C29(H29A,H29B,H29C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.210
_oxdiff_exptl_absorpt_empirical_full_min 0.856
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'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
O3 O 0.38481(18) 0.21131(7) 0.63953(6) 0.0220(2) Uani 1 1 d . . . . .
O9 O 0.2582(2) 0.55505(7) 0.50916(6) 0.0255(3) Uani 1 1 d . . . . .
O31 O 0.2856(2) 0.14436(8) 0.77061(6) 0.0282(3) Uani 1 1 d . . . . .
O32 O 0.0350(2) 0.19158(8) 0.61761(7) 0.0324(3) Uani 1 1 d . . . . .
N1 N 0.2642(3) 0.09276(9) 0.63492(7) 0.0279(3) Uani 1 1 d . . . . .
H1 H 0.171153 0.059886 0.622729 0.034 Uiso 1 1 calc R . . . .
C13 C 0.4888(2) 0.42615(9) 0.62920(8) 0.0200(3) Uani 1 1 d . . . . .
H13 H 0.370835 0.438560 0.657520 0.024 Uiso 1 1 calc R . . . .
C25 C 0.1999(3) 0.31230(10) 0.70043(8) 0.0235(3) Uani 1 1 d . . . . .
H25A H 0.079366 0.316484 0.672987 0.035 Uiso 1 1 calc GR . . . .
H25B H 0.222666 0.360463 0.721597 0.035 Uiso 1 1 calc GR . . . .
H25C H 0.174997 0.272808 0.731353 0.035 Uiso 1 1 calc GR . . . .
C5 C 0.4371(3) 0.34442(9) 0.60209(8) 0.0206(3) Uani 1 1 d . . . . .
C18 C 0.4590(3) 0.15829(11) 0.74793(8) 0.0247(3) Uani 1 1 d . . . . .
C12 C 0.4870(3) 0.48959(9) 0.57802(8) 0.0213(3) Uani 1 1 d . . . . .
C28 C 0.1480(3) 0.73634(11) 0.58442(8) 0.0272(4) Uani 1 1 d . . . . .
C2 C 0.2100(3) 0.16898(10) 0.63050(8) 0.0252(4) Uani 1 1 d . . . . .
C6 C 0.2389(3) 0.34716(10) 0.55881(8) 0.0239(3) Uani 1 1 d . . . . .
H6A H 0.225422 0.298024 0.537425 0.029 Uiso 1 1 calc R . . . .
H6B H 0.115002 0.353712 0.585367 0.029 Uiso 1 1 calc R . . . .
C7 C 0.2401(3) 0.41125(9) 0.50840(8) 0.0245(3) Uani 1 1 d . . . . .
H7A H 0.353585 0.403213 0.478190 0.029 Uiso 1 1 calc R . . . .
H7B H 0.106879 0.412455 0.485653 0.029 Uiso 1 1 calc R . . . .
C16 C 0.5952(3) 0.28802(9) 0.70316(8) 0.0217(3) Uani 1 1 d . . . . .
H16 H 0.710581 0.267767 0.677035 0.026 Uiso 1 1 calc R . . . .
C8 C 0.2732(3) 0.48519(9) 0.54469(8) 0.0221(3) Uani 1 1 d . . . . .
H8 H 0.164368 0.487282 0.577710 0.026 Uiso 1 1 calc R . . . .
C4 C 0.3954(3) 0.29180(10) 0.66115(8) 0.0210(3) Uani 1 1 d . . . . .
C27 C 0.1605(3) 0.66040(10) 0.57803(8) 0.0256(4) Uani 1 1 d . . . . .
H27 H 0.043817 0.632494 0.591836 0.031 Uiso 1 1 calc R . . . .
C11 C 0.4666(3) 0.57186(10) 0.60392(8) 0.0232(3) Uani 1 1 d . . . . .
H11A H 0.604423 0.595146 0.609943 0.028 Uiso 1 1 calc R . . . .
H11B H 0.390863 0.572397 0.643922 0.028 Uiso 1 1 calc R . . . .
C26 C 0.6189(3) 0.30933(10) 0.56225(8) 0.0242(3) Uani 1 1 d . . . . .
H26A H 0.604121 0.324953 0.518807 0.036 Uiso 1 1 calc GR . . . .
H26B H 0.613059 0.254262 0.564857 0.036 Uiso 1 1 calc GR . . . .
H26C H 0.752165 0.327020 0.578403 0.036 Uiso 1 1 calc GR . . . .
C24 C 0.4582(3) 0.06295(10) 0.65759(8) 0.0276(4) Uani 1 1 d . . . . .
C19 C 0.5655(3) 0.09707(10) 0.70919(8) 0.0253(4) Uani 1 1 d . . . . .
C15 C 0.6610(3) 0.36847(10) 0.72613(8) 0.0239(3) Uani 1 1 d . . . . .
H15A H 0.555563 0.387517 0.755598 0.029 Uiso 1 1 calc R . . . .
H15B H 0.794074 0.364576 0.748751 0.029 Uiso 1 1 calc R . . . .
C14 C 0.6855(3) 0.42612(10) 0.67163(8) 0.0230(3) Uani 1 1 d . . . . .
H14A H 0.707326 0.477226 0.688847 0.028 Uiso 1 1 calc R . . . .
H14B H 0.808616 0.412735 0.646526 0.028 Uiso 1 1 calc R . . . .
C10 C 0.3394(3) 0.61442(10) 0.55132(8) 0.0246(4) Uani 1 1 d . . . . .
H10 H 0.434332 0.648436 0.527632 0.030 Uiso 1 1 calc R . . . .
C17 C 0.5690(3) 0.23373(10) 0.76097(8) 0.0257(4) Uani 1 1 d . . . . .
H17A H 0.708162 0.222745 0.778031 0.031 Uiso 1 1 calc R . . . .
H17B H 0.490326 0.260848 0.793498 0.031 Uiso 1 1 calc R . . . .
C23 C 0.5463(4) -0.00036(11) 0.62779(9) 0.0337(4) Uani 1 1 d . . . . .
H23 H 0.476133 -0.023119 0.593869 0.040 Uiso 1 1 calc R . . . .
C20 C 0.7628(3) 0.06913(11) 0.72687(9) 0.0291(4) Uani 1 1 d . . . . .
H20 H 0.838738 0.093733 0.758709 0.035 Uiso 1 1 calc R . . . .
C0AA C 0.6726(3) 0.48877(11) 0.53117(9) 0.0266(4) Uani 1 1 d . . . . .
H0AA H 0.802753 0.495151 0.553944 0.040 Uiso 1 1 calc GR . . . .
H0AB H 0.656323 0.530029 0.501317 0.040 Uiso 1 1 calc GR . . . .
H0AC H 0.674663 0.440617 0.508920 0.040 Uiso 1 1 calc GR . . . .
C21 C 0.8474(3) 0.00450(11) 0.69718(10) 0.0356(4) Uani 1 1 d . . . . .
H21 H 0.976757 -0.015290 0.710297 0.043 Uiso 1 1 calc R . . . .
C22 C 0.7376(4) -0.03008(11) 0.64800(10) 0.0388(5) Uani 1 1 d . . . . .
H22 H 0.792868 -0.073577 0.628437 0.047 Uiso 1 1 calc R . . . .
C30 C -0.0455(4) 0.77240(12) 0.61324(10) 0.0352(4) Uani 1 1 d . . . . .
H30A H -0.114720 0.803897 0.582143 0.053 Uiso 1 1 calc GR . . . .
H30B H -0.004976 0.803547 0.648804 0.053 Uiso 1 1 calc GR . . . .
H30C H -0.140422 0.732778 0.627165 0.053 Uiso 1 1 calc GR . . . .
C29 C 0.3178(3) 0.79191(11) 0.56515(10) 0.0343(4) Uani 1 1 d . . . . .
H29A H 0.434578 0.764143 0.547238 0.052 Uiso 1 1 calc GR . . . .
H29B H 0.364906 0.820066 0.601672 0.052 Uiso 1 1 calc GR . . . .
H29C H 0.262572 0.827064 0.534204 0.052 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 0.0181 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
C2 O3 C4 127.05(13) . . ?
C8 O9 C10 105.03(12) . . ?
C2 N1 H1 116.8 . . ?
C2 N1 C24 126.39(15) . . ?
C24 N1 H1 116.8 . . ?
C5 C13 H13 105.2 . . ?
C12 C13 H13 105.2 . . ?
C12 C13 C5 113.08(13) . . ?
C14 C13 H13 105.2 . . ?
C14 C13 C5 112.47(13) . . ?
C14 C13 C12 114.48(14) . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C4 C25 H25A 109.5 . . ?
C4 C25 H25B 109.5 . . ?
C4 C25 H25C 109.5 . . ?
C13 C5 C4 105.96(12) . . ?
C6 C5 C13 110.83(13) . . ?
C6 C5 C4 110.42(14) . . ?
C26 C5 C13 113.59(14) . . ?
C26 C5 C6 107.06(13) . . ?
C26 C5 C4 109.00(13) . . ?
O31 C18 C19 118.37(17) . . ?
O31 C18 C17 121.01(16) . . ?
C19 C18 C17 120.56(15) . . ?
C8 C12 C13 107.02(13) . . ?
C8 C12 C11 97.79(13) . . ?
C8 C12 C0AA 112.40(14) . . ?
C11 C12 C13 114.69(13) . . ?
C0AA C12 C13 115.97(14) . . ?
C0AA C12 C11 107.57(14) . . ?
C27 C28 C30 120.23(19) . . ?
C27 C28 C29 124.71(19) . . ?
C29 C28 C30 115.06(17) . . ?
O3 C2 N1 108.33(15) . . ?
O32 C2 O3 127.57(16) . . ?
O32 C2 N1 124.01(17) . . ?
C5 C6 H6A 108.5 . . ?
C5 C6 H6B 108.5 . . ?
H6A C6 H6B 107.5 . . ?
C7 C6 C5 115.08(14) . . ?
C7 C6 H6A 108.5 . . ?
C7 C6 H6B 108.5 . . ?
C6 C7 H7A 110.6 . . ?
C6 C7 H7B 110.6 . . ?
H7A C7 H7B 108.8 . . ?
C8 C7 C6 105.50(13) . . ?
C8 C7 H7A 110.6 . . ?
C8 C7 H7B 110.6 . . ?
C4 C16 H16 107.6 . . ?
C4 C16 C17 112.90(14) . . ?
C15 C16 H16 107.6 . . ?
C15 C16 C4 111.30(13) . . ?
C15 C16 C17 109.60(13) . . ?
C17 C16 H16 107.6 . . ?
O9 C8 C12 104.91(13) . . ?
O9 C8 C7 116.65(13) . . ?
O9 C8 H8 107.1 . . ?
C12 C8 H8 107.1 . . ?
C7 C8 C12 113.50(14) . . ?
C7 C8 H8 107.1 . . ?
O3 C4 C25 110.59(13) . . ?
O3 C4 C5 108.45(12) . . ?
O3 C4 C16 100.03(12) . . ?
C25 C4 C5 115.46(14) . . ?
C25 C4 C16 111.15(13) . . ?
C16 C4 C5 110.03(13) . . ?
C28 C27 H27 116.1 . . ?
C28 C27 C10 127.87(18) . . ?
C10 C27 H27 116.1 . . ?
C12 C11 H11A 111.1 . . ?
C12 C11 H11B 111.1 . . ?
C12 C11 C10 103.48(13) . . ?
H11A C11 H11B 109.0 . . ?
C10 C11 H11A 111.1 . . ?
C10 C11 H11B 111.1 . . ?
C5 C26 H26A 109.5 . . ?
C5 C26 H26B 109.5 . . ?
C5 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C19 C24 N1 121.51(16) . . ?
C23 C24 N1 119.13(18) . . ?
C23 C24 C19 119.35(18) . . ?
C24 C19 C18 120.08(16) . . ?
C20 C19 C18 120.31(16) . . ?
C20 C19 C24 119.40(17) . . ?
C16 C15 H15A 109.0 . . ?
C16 C15 H15B 109.0 . . ?
H15A C15 H15B 107.8 . . ?
C14 C15 C16 112.73(14) . . ?
C14 C15 H15A 109.0 . . ?
C14 C15 H15B 109.0 . . ?
C13 C14 C15 110.83(14) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C15 C14 H14A 109.5 . . ?
C15 C14 H14B 109.5 . . ?
H14A C14 H14B 108.1 . . ?
O9 C10 C27 110.00(14) . . ?
O9 C10 C11 106.25(13) . . ?
O9 C10 H10 109.5 . . ?
C27 C10 C11 112.15(14) . . ?
C27 C10 H10 109.5 . . ?
C11 C10 H10 109.5 . . ?
C18 C17 C16 115.80(14) . . ?
C18 C17 H17A 108.3 . . ?
C18 C17 H17B 108.3 . . ?
C16 C17 H17A 108.3 . . ?
C16 C17 H17B 108.3 . . ?
H17A C17 H17B 107.4 . . ?
C24 C23 H23 119.7 . . ?
C22 C23 C24 120.6(2) . . ?
C22 C23 H23 119.7 . . ?
C19 C20 H20 119.8 . . ?
C19 C20 C21 120.43(19) . . ?
C21 C20 H20 119.8 . . ?
C12 C0AA H0AA 109.5 . . ?
C12 C0AA H0AB 109.5 . . ?
C12 C0AA H0AC 109.5 . . ?
H0AA C0AA H0AB 109.5 . . ?
H0AA C0AA H0AC 109.5 . . ?
H0AB C0AA H0AC 109.5 . . ?
C20 C21 H21 120.2 . . ?
C22 C21 C20 119.58(19) . . ?
C22 C21 H21 120.2 . . ?
C23 C22 C21 120.48(18) . . ?
C23 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
C28 C30 H30A 109.5 . . ?
C28 C30 H30B 109.5 . . ?
C28 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 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
O3 C2 1.342(2) . ?
O3 C4 1.4739(19) . ?
O9 C8 1.431(2) . ?
O9 C10 1.456(2) . ?
O31 C18 1.222(2) . ?
O32 C2 1.206(2) . ?
N1 H1 0.8600 . ?
N1 C2 1.372(2) . ?
N1 C24 1.416(3) . ?
C13 H13 0.9800 . ?
C13 C5 1.567(2) . ?
C13 C12 1.543(2) . ?
C13 C14 1.533(2) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C25 C4 1.531(2) . ?
C5 C6 1.552(2) . ?
C5 C4 1.568(2) . ?
C5 C26 1.550(2) . ?
C18 C19 1.502(2) . ?
C18 C17 1.510(3) . ?
C12 C8 1.526(2) . ?
C12 C11 1.537(2) . ?
C12 C0AA 1.534(2) . ?
C28 C27 1.330(3) . ?
C28 C30 1.504(3) . ?
C28 C29 1.501(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.540(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.511(2) . ?
C16 H16 0.9800 . ?
C16 C4 1.545(2) . ?
C16 C15 1.538(2) . ?
C16 C17 1.551(2) . ?
C8 H8 0.9800 . ?
C27 H27 0.9300 . ?
C27 C10 1.496(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C10 1.557(2) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C24 C19 1.413(3) . ?
C24 C23 1.385(3) . ?
C19 C20 1.390(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C14 1.533(2) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C10 H10 0.9800 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C23 H23 0.9300 . ?
C23 C22 1.383(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.394(3) . ?
C0AA H0AA 0.9600 . ?
C0AA H0AB 0.9600 . ?
C0AA H0AC 0.9600 . ?
C21 H21 0.9300 . ?
C21 C22 1.386(3) . ?
C22 H22 0.9300 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
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
O31 C18 C19 C24 53.6(2) . . . . ?
O31 C18 C19 C20 -121.12(18) . . . . ?
O31 C18 C17 C16 -112.90(18) . . . . ?
N1 C24 C19 C18 9.8(2) . . . . ?
N1 C24 C19 C20 -175.44(16) . . . . ?
N1 C24 C23 C22 178.82(17) . . . . ?
C13 C5 C6 C7 48.88(19) . . . . ?
C13 C5 C4 O3 -169.65(12) . . . . ?
C13 C5 C4 C25 65.63(17) . . . . ?
C13 C5 C4 C16 -61.16(16) . . . . ?
C13 C12 C8 O9 166.50(12) . . . . ?
C13 C12 C8 C7 -65.04(17) . . . . ?
C13 C12 C11 C10 -147.37(14) . . . . ?
C5 C13 C12 C8 54.31(17) . . . . ?
C5 C13 C12 C11 161.57(13) . . . . ?
C5 C13 C12 C0AA -72.02(18) . . . . ?
C5 C13 C14 C15 -56.47(18) . . . . ?
C5 C6 C7 C8 -55.28(18) . . . . ?
C18 C19 C20 C21 170.00(17) . . . . ?
C12 C13 C5 C6 -47.73(18) . . . . ?
C12 C13 C5 C4 -167.54(13) . . . . ?
C12 C13 C5 C26 72.84(17) . . . . ?
C12 C13 C14 C15 172.65(14) . . . . ?
C12 C11 C10 O9 12.17(17) . . . . ?
C12 C11 C10 C27 132.39(15) . . . . ?
C28 C27 C10 O9 -136.18(19) . . . . ?
C28 C27 C10 C11 105.8(2) . . . . ?
C2 O3 C4 C25 25.7(2) . . . . ?
C2 O3 C4 C5 -101.85(17) . . . . ?
C2 O3 C4 C16 142.95(15) . . . . ?
C2 N1 C24 C19 37.6(3) . . . . ?
C2 N1 C24 C23 -141.31(19) . . . . ?
C6 C5 C4 O3 70.28(16) . . . . ?
C6 C5 C4 C25 -54.44(18) . . . . ?
C6 C5 C4 C16 178.77(13) . . . . ?
C6 C7 C8 O9 -173.58(14) . . . . ?
C6 C7 C8 C12 64.27(18) . . . . ?
C16 C15 C14 C13 51.16(18) . . . . ?
C8 O9 C10 C27 -103.93(15) . . . . ?
C8 O9 C10 C11 17.67(17) . . . . ?
C8 C12 C11 C10 -34.55(16) . . . . ?
C4 O3 C2 O32 26.6(3) . . . . ?
C4 O3 C2 N1 -156.66(14) . . . . ?
C4 C5 C6 C7 165.99(14) . . . . ?
C4 C16 C15 C14 -53.17(19) . . . . ?
C4 C16 C17 C18 42.3(2) . . . . ?
C11 C12 C8 O9 47.63(15) . . . . ?
C11 C12 C8 C7 176.09(14) . . . . ?
C26 C5 C6 C7 -75.49(17) . . . . ?
C26 C5 C4 O3 -47.05(17) . . . . ?
C26 C5 C4 C25 -171.77(14) . . . . ?
C26 C5 C4 C16 61.43(17) . . . . ?
C24 N1 C2 O3 11.8(2) . . . . ?
C24 N1 C2 O32 -171.35(18) . . . . ?
C24 C19 C20 C21 -4.8(3) . . . . ?
C24 C23 C22 C21 -2.0(3) . . . . ?
C19 C18 C17 C16 70.0(2) . . . . ?
C19 C24 C23 C22 -0.2(3) . . . . ?
C19 C20 C21 C22 2.6(3) . . . . ?
C15 C16 C4 O3 172.98(13) . . . . ?
C15 C16 C4 C25 -70.18(18) . . . . ?
C15 C16 C4 C5 58.99(17) . . . . ?
C15 C16 C17 C18 166.95(14) . . . . ?
C14 C13 C5 C6 -179.31(13) . . . . ?
C14 C13 C5 C4 60.88(17) . . . . ?
C14 C13 C5 C26 -58.74(18) . . . . ?
C14 C13 C12 C8 -175.12(13) . . . . ?
C14 C13 C12 C11 -67.85(18) . . . . ?
C14 C13 C12 C0AA 58.55(19) . . . . ?
C10 O9 C8 C12 -41.78(15) . . . . ?
C10 O9 C8 C7 -168.32(15) . . . . ?
C17 C18 C19 C24 -129.25(17) . . . . ?
C17 C18 C19 C20 56.0(2) . . . . ?
C17 C16 C4 O3 -63.27(16) . . . . ?
C17 C16 C4 C25 53.57(18) . . . . ?
C17 C16 C4 C5 -177.26(13) . . . . ?
C17 C16 C15 C14 -178.77(14) . . . . ?
C23 C24 C19 C18 -171.26(16) . . . . ?
C23 C24 C19 C20 3.5(3) . . . . ?
C20 C21 C22 C23 0.8(3) . . . . ?
C0AA C12 C8 O9 -65.07(16) . . . . ?
C0AA C12 C8 C7 63.39(19) . . . . ?
C0AA C12 C11 C10 82.00(16) . . . . ?
C30 C28 C27 C10 -179.33(17) . . . . ?
C29 C28 C27 C10 0.1(3) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 156580972
