#------------------------------------------------------------------------------
#$Date: 2025-08-19 15:18:28 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301805 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/73/2227311.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_2227311
loop_
_publ_author_name
'Aree, Thammarat'
'Antia, Bassey S.'
'Ekpa, Okon D.'
'Kittakoop, Prasat'
_publ_section_title
;
 Paraherquamide E
;
_journal_coeditor_code           CI5149
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2227
_journal_paper_doi               10.1107/S1600536810030795
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C28 H35 N3 O4'
_chemical_formula_moiety         'C28 H35 N3 O4'
_chemical_formula_sum            'C28 H35 N3 O4'
_chemical_formula_weight         477.59
_chemical_melting_point          ?
_chemical_name_common
;
(1'R,5'aS,7'R,8'aS,9'aR)-2',3',8'a,9'-
tetrahydro-1'-hydroxy-1',4,4,8',8',11'-hexamethyl-14-
deoxyspiro[4H,8H-1,4-dioxepino[2,3-g]indole-
8,7'(8'H)-[5H,6H-
5a,9a](iminomethano)[1H]cyclopent[f]indolizine]-
9,10'(10H)-dione
;
_chemical_name_systematic        'Paraherquamide E'
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.5069(2)
_cell_length_b                   16.0351(8)
_cell_length_c                   23.9713(11)
_cell_measurement_reflns_used    1372
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      19.70
_cell_measurement_theta_min      2.54
_cell_volume                     2501.14(19)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    'Mercury (Macrae et al. 2006)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.824
_diffrn_measurement_device_type  'Bruker SMART APEXII CCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0493
_diffrn_reflns_av_sigmaI/netI    0.0732
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            8444
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.18
_diffrn_reflns_theta_min         1.53
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.9543
_exptl_absorpt_correction_T_min  0.9457
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.197
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.980
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     322
_refine_ls_number_reflns         2889
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.980
_refine_ls_R_factor_all          0.1059
_refine_ls_R_factor_gt           0.0486
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0463P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0842
_refine_ls_wR_factor_ref         0.1022
_reflns_number_gt                1746
_reflns_number_total             2889
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci5149.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value 'not measured' was changed to '?' -
the value is undefined or not given.

Automatic conversion script
Id: cif_fix_values 1569 2011-02-09 13:29:24Z adriana 
;
_cod_database_code               2227311
_cod_database_fobs_code          2227311
loop_
_symmetry_equiv_pos_as_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_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_disorder_assembly
_atom_site_disorder_group
N N1 0.0595(4) 0.84401(16) 0.16792(11) 0.0366(7) Uani d . 1 . .
H H1 -0.0514 0.8699 0.1769 0.044 Uiso calc R 1 . .
N N2 0.6009(5) 0.47354(18) 0.15605(13) 0.0452(8) Uani d . 1 . .
N N3 0.3520(4) 0.54738(18) 0.23432(11) 0.0353(7) Uani d . 1 . .
O O1 -0.0133(4) 0.71770(14) 0.20826(10) 0.0510(7) Uani d . 1 . .
O O2 0.4573(4) 1.06380(14) 0.07563(9) 0.0421(7) Uani d . 1 . .
O O3 0.0828(4) 1.01425(14) 0.13216(10) 0.0468(7) Uani d . 1 . .
O O4 0.2499(4) 0.41513(15) 0.25453(10) 0.0543(7) Uani d . 1 . .
C C2 0.0988(6) 0.7623(2) 0.17997(14) 0.0364(9) Uani d . 1 . .
C C3 0.3025(5) 0.73668(19) 0.15236(13) 0.0293(8) Uani d . 1 . .
C C4 0.5582(5) 0.8436(2) 0.10529(14) 0.0387(9) Uani d . 1 . .
H H4 0.6645 0.8054 0.1007 0.046 Uiso calc R 1 . .
C C5 0.5796(5) 0.9252(2) 0.08689(14) 0.0396(9) Uani d . 1 . .
H H5 0.7014 0.9414 0.0697 0.047 Uiso calc R 1 . .
C C6 0.4235(5) 0.9831(2) 0.09359(13) 0.0336(8) Uani d . 1 . .
C C7 0.2432(6) 0.9606(2) 0.12015(14) 0.0327(8) Uani d . 1 . .
C C8 0.2239(5) 0.8798(2) 0.13901(14) 0.0314(8) Uani d . 1 . .
C C9 0.3764(5) 0.8200(2) 0.13052(13) 0.0321(8) Uani d . 1 . .
C C10 0.4413(6) 0.6932(2) 0.19609(14) 0.0393(9) Uani d . 1 . .
H H10A 0.5828 0.7110 0.1916 0.047 Uiso calc R 1 . .
H H10B 0.3968 0.7074 0.2335 0.047 Uiso calc R 1 . .
C C11 0.4239(5) 0.5991(2) 0.18678(12) 0.0308(8) Uani d . 1 . .
C C12 0.6319(5) 0.5608(2) 0.17134(15) 0.0434(10) Uani d . 1 . .
H H12A 0.6918 0.5910 0.1403 0.052 Uiso calc R 1 . .
H H12B 0.7252 0.5646 0.2028 0.052 Uiso calc R 1 . .
C C13 0.3851(5) 0.4474(2) 0.16074(14) 0.0353(9) Uani d . 1 . .
C C14 0.4053(6) 0.3551(2) 0.14645(17) 0.0553(11) Uani d . 1 . .
H H14 0.4357 0.3520 0.1065 0.066 Uiso calc R 1 . .
C C15 0.6035(8) 0.3309(3) 0.1771(2) 0.0952(18) Uani d . 1 . .
H H15A 0.5717 0.3047 0.2126 0.114 Uiso calc R 1 . .
H H15B 0.6839 0.2923 0.1549 0.114 Uiso calc R 1 . .
C C16 0.7211(7) 0.4117(3) 0.1863(2) 0.0831(16) Uani d . 1 . .
H H16A 0.7289 0.4254 0.2256 0.100 Uiso calc R 1 . .
H H16B 0.8593 0.4078 0.1713 0.100 Uiso calc R 1 . .
C C17 0.2264(8) 0.2967(2) 0.15698(19) 0.0720(14) Uani d . 1 . .
H H17A 0.1929 0.2970 0.1960 0.108 Uiso calc R 1 . .
H H17B 0.2634 0.2412 0.1458 0.108 Uiso calc R 1 . .
H H17C 0.1094 0.3149 0.1358 0.108 Uiso calc R 1 . .
C C18 0.3167(5) 0.4666(2) 0.22117(14) 0.0377(9) Uani d . 1 . .
C C19 0.2626(6) 0.50045(19) 0.11950(13) 0.0371(9) Uani d . 1 . .
H H19A 0.1244 0.4786 0.1156 0.045 Uiso calc R 1 . .
H H19B 0.3282 0.4998 0.0832 0.045 Uiso calc R 1 . .
C C20 0.2558(5) 0.58959(18) 0.14247(12) 0.0282(8) Uani d . 1 . .
H H20 0.1259 0.5933 0.1630 0.034 Uiso calc R 1 . .
C C21 0.2623(5) 0.66842(19) 0.10578(13) 0.0311(8) Uani d . 1 . .
C C22 0.4342(6) 0.6665(2) 0.06154(14) 0.0441(10) Uani d . 1 . .
H H22A 0.5655 0.6642 0.0798 0.066 Uiso calc R 1 . .
H H22B 0.4266 0.7159 0.0390 0.066 Uiso calc R 1 . .
H H22C 0.4175 0.6182 0.0383 0.066 Uiso calc R 1 . .
C C23 0.0595(6) 0.6830(2) 0.07491(15) 0.0463(10) Uani d . 1 . .
H H23A 0.0437 0.6417 0.0462 0.069 Uiso calc R 1 . .
H H23B 0.0603 0.7375 0.0584 0.069 Uiso calc R 1 . .
H H23C -0.0527 0.6788 0.1008 0.069 Uiso calc R 1 . .
C C24 0.0153(6) 1.0726(2) 0.09430(16) 0.0498(10) Uani d . 1 . .
H H24 -0.1173 1.0923 0.1003 0.060 Uiso calc R 1 . .
C C25 0.1105(6) 1.1046(2) 0.05100(17) 0.0523(11) Uani d . 1 . .
H H25 0.0318 1.1411 0.0298 0.063 Uiso calc R 1 . .
C C26 0.3240(6) 1.0919(2) 0.03039(14) 0.0456(10) Uani d . 1 . .
C C27 0.4195(8) 1.1744(2) 0.0128(2) 0.0788(15) Uani d . 1 . .
H H27A 0.4292 1.2107 0.0446 0.118 Uiso calc R 1 . .
H H27B 0.3351 1.2001 -0.0152 0.118 Uiso calc R 1 . .
H H27C 0.5543 1.1646 -0.0021 0.118 Uiso calc R 1 . .
C C28 0.3285(7) 1.0286(3) -0.01689(16) 0.0696(14) Uani d . 1 . .
H H28A 0.4682 1.0189 -0.0280 0.104 Uiso calc R 1 . .
H H28B 0.2518 1.0497 -0.0480 0.104 Uiso calc R 1 . .
H H28C 0.2685 0.9771 -0.0044 0.104 Uiso calc R 1 . .
C C29 0.3185(8) 0.5797(3) 0.28994(15) 0.0709(14) Uani d . 1 . .
H H29A 0.2896 0.5344 0.3149 0.106 Uiso calc R 1 . .
H H29B 0.2042 0.6175 0.2895 0.106 Uiso calc R 1 . .
H H29C 0.4394 0.6086 0.3023 0.106 Uiso calc R 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 0.0016 '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'
O O 0.0106 0.0060 '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'
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
C2 N1 C8 . . 110.8(3) ?
C2 N1 H1 . . 124.6 ?
C8 N1 H1 . . 124.6 ?
C16 N2 C12 . . 117.0(3) ?
C16 N2 C13 . . 106.3(3) ?
C12 N2 C13 . . 112.7(3) ?
C18 N3 C29 . . 122.1(3) ?
C18 N3 C11 . . 114.2(3) ?
C29 N3 C11 . . 123.7(3) ?
C6 O2 C26 . . 115.2(3) ?
C24 O3 C7 . . 121.8(3) ?
O1 C2 N1 . . 124.4(3) ?
O1 C2 C3 . . 126.5(3) ?
N1 C2 C3 . . 109.1(3) ?
C9 C3 C2 . . 100.8(3) ?
C9 C3 C10 . . 116.5(3) ?
C2 C3 C10 . . 109.4(3) ?
C9 C3 C21 . . 114.7(2) ?
C2 C3 C21 . . 110.2(3) ?
C10 C3 C21 . . 105.2(2) ?
C9 C4 C5 . . 118.9(3) ?
C9 C4 H4 . . 120.6 ?
C5 C4 H4 . . 120.6 ?
C6 C5 C4 . . 121.4(3) ?
C6 C5 H5 . . 119.3 ?
C4 C5 H5 . . 119.3 ?
O2 C6 C7 . . 121.5(3) ?
O2 C6 C5 . . 118.3(3) ?
C7 C6 C5 . . 120.1(3) ?
C8 C7 C6 . . 118.3(3) ?
C8 C7 O3 . . 116.6(3) ?
C6 C7 O3 . . 125.1(3) ?
C7 C8 C9 . . 122.3(3) ?
C7 C8 N1 . . 128.2(3) ?
C9 C8 N1 . . 109.5(3) ?
C4 C9 C8 . . 119.0(3) ?
C4 C9 C3 . . 131.7(3) ?
C8 C9 C3 . . 109.3(3) ?
C11 C10 C3 . . 107.6(3) ?
C11 C10 H10A . . 110.2 ?
C3 C10 H10A . . 110.2 ?
C11 C10 H10B . . 110.2 ?
C3 C10 H10B . . 110.2 ?
H10A C10 H10B . . 108.5 ?
N3 C11 C10 . . 117.5(3) ?
N3 C11 C12 . . 103.8(3) ?
C10 C11 C12 . . 111.5(3) ?
N3 C11 C20 . . 104.5(2) ?
C10 C11 C20 . . 104.6(3) ?
C12 C11 C20 . . 115.0(3) ?
N2 C12 C11 . . 108.9(3) ?
N2 C12 H12A . . 109.9 ?
C11 C12 H12A . . 109.9 ?
N2 C12 H12B . . 109.9 ?
C11 C12 H12B . . 109.9 ?
H12A C12 H12B . . 108.3 ?
N2 C13 C14 . . 100.2(3) ?
N2 C13 C19 . . 106.9(3) ?
C14 C13 C19 . . 116.1(3) ?
N2 C13 C18 . . 106.9(3) ?
C14 C13 C18 . . 115.3(3) ?
C19 C13 C18 . . 110.2(3) ?
C17 C14 C13 . . 119.7(3) ?
C17 C14 C15 . . 114.2(3) ?
C13 C14 C15 . . 102.1(4) ?
C17 C14 H14 . . 106.7 ?
C13 C14 H14 . . 106.7 ?
C15 C14 H14 . . 106.7 ?
C16 C15 C14 . . 106.0(3) ?
C16 C15 H15A . . 110.5 ?
C14 C15 H15A . . 110.5 ?
C16 C15 H15B . . 110.5 ?
C14 C15 H15B . . 110.5 ?
H15A C15 H15B . . 108.7 ?
N2 C16 C15 . . 103.8(4) ?
N2 C16 H16A . . 111.0 ?
C15 C16 H16A . . 111.0 ?
N2 C16 H16B . . 111.0 ?
C15 C16 H16B . . 111.0 ?
H16A C16 H16B . . 109.0 ?
C14 C17 H17A . . 109.5 ?
C14 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
C14 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
O4 C18 N3 . . 123.5(3) ?
O4 C18 C13 . . 125.3(3) ?
N3 C18 C13 . . 111.1(3) ?
C13 C19 C20 . . 107.6(3) ?
C13 C19 H19A . . 110.2 ?
C20 C19 H19A . . 110.2 ?
C13 C19 H19B . . 110.2 ?
C20 C19 H19B . . 110.2 ?
H19A C19 H19B . . 108.5 ?
C19 C20 C11 . . 108.8(3) ?
C19 C20 C21 . . 124.0(3) ?
C11 C20 C21 . . 107.1(2) ?
C19 C20 H20 . . 105.2 ?
C11 C20 H20 . . 105.2 ?
C21 C20 H20 . . 105.2 ?
C23 C21 C20 . . 112.2(3) ?
C23 C21 C22 . . 107.2(3) ?
C20 C21 C22 . . 113.4(3) ?
C23 C21 C3 . . 112.2(3) ?
C20 C21 C3 . . 99.7(2) ?
C22 C21 C3 . . 112.3(3) ?
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 ?
C21 C23 H23A . . 109.5 ?
C21 C23 H23B . . 109.5 ?
H23A C23 H23B . . 109.5 ?
C21 C23 H23C . . 109.5 ?
H23A C23 H23C . . 109.5 ?
H23B C23 H23C . . 109.5 ?
C25 C24 O3 . . 129.5(4) ?
C25 C24 H24 . . 115.2 ?
O3 C24 H24 . . 115.2 ?
C24 C25 C26 . . 130.5(4) ?
C24 C25 H25 . . 114.8 ?
C26 C25 H25 . . 114.8 ?
O2 C26 C25 . . 110.5(3) ?
O2 C26 C28 . . 109.7(3) ?
C25 C26 C28 . . 110.9(3) ?
O2 C26 C27 . . 103.4(3) ?
C25 C26 C27 . . 110.7(3) ?
C28 C26 C27 . . 111.5(3) ?
C26 C27 H27A . . 109.5 ?
C26 C27 H27B . . 109.5 ?
H27A C27 H27B . . 109.5 ?
C26 C27 H27C . . 109.5 ?
H27A C27 H27C . . 109.5 ?
H27B C27 H27C . . 109.5 ?
C26 C28 H28A . . 109.5 ?
C26 C28 H28B . . 109.5 ?
H28A C28 H28B . . 109.5 ?
C26 C28 H28C . . 109.5 ?
H28A C28 H28C . . 109.5 ?
H28B C28 H28C . . 109.5 ?
N3 C29 H29A . . 109.5 ?
N3 C29 H29B . . 109.5 ?
H29A C29 H29B . . 109.5 ?
N3 C29 H29C . . 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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C2 . 1.366(4) ?
N1 C8 . 1.398(4) ?
N1 H1 . 0.86 ?
N2 C16 . 1.456(5) ?
N2 C12 . 1.460(4) ?
N2 C13 . 1.470(5) ?
N3 C18 . 1.353(4) ?
N3 C29 . 1.447(4) ?
N3 C11 . 1.485(4) ?
O1 C2 . 1.226(4) ?
O2 C6 . 1.382(4) ?
O2 C26 . 1.460(4) ?
O3 C24 . 1.376(4) ?
O3 C7 . 1.383(4) ?
O4 C18 . 1.228(4) ?
C2 C3 . 1.537(5) ?
C3 C9 . 1.513(4) ?
C3 C10 . 1.550(4) ?
C3 C21 . 1.585(4) ?
C4 C9 . 1.382(5) ?
C4 C5 . 1.388(4) ?
C4 H4 . 0.93 ?
C5 C6 . 1.385(5) ?
C5 H5 . 0.93 ?
C6 C7 . 1.382(5) ?
C7 C8 . 1.378(4) ?
C8 C9 . 1.395(5) ?
C10 C11 . 1.529(5) ?
C10 H10A . 0.97 ?
C10 H10B . 0.97 ?
C11 C12 . 1.532(5) ?
C11 C20 . 1.533(4) ?
C12 H12A . 0.97 ?
C12 H12B . 0.97 ?
C13 C14 . 1.525(5) ?
C13 C19 . 1.528(5) ?
C13 C18 . 1.546(5) ?
C14 C17 . 1.516(6) ?
C14 C15 . 1.534(6) ?
C14 H14 . 0.98 ?
C15 C16 . 1.521(7) ?
C15 H15A . 0.97 ?
C15 H15B . 0.97 ?
C16 H16A . 0.97 ?
C16 H16B . 0.97 ?
C17 H17A . 0.96 ?
C17 H17B . 0.96 ?
C17 H17C . 0.96 ?
C19 C20 . 1.532(4) ?
C19 H19A . 0.97 ?
C19 H19B . 0.97 ?
C20 C21 . 1.541(4) ?
C20 H20 . 0.98 ?
C21 C23 . 1.531(5) ?
C21 C22 . 1.541(5) ?
C22 H22A . 0.96 ?
C22 H22B . 0.96 ?
C22 H22C . 0.96 ?
C23 H23A . 0.96 ?
C23 H23B . 0.96 ?
C23 H23C . 0.96 ?
C24 C25 . 1.313(5) ?
C24 H24 . 0.93 ?
C25 C26 . 1.489(5) ?
C25 H25 . 0.93 ?
C26 C28 . 1.522(5) ?
C26 C27 . 1.522(5) ?
C27 H27A . 0.96 ?
C27 H27B . 0.96 ?
C27 H27C . 0.96 ?
C28 H28A . 0.96 ?
C28 H28B . 0.96 ?
C28 H28C . 0.96 ?
C29 H29A . 0.96 ?
C29 H29B . 0.96 ?
C29 H29C . 0.96 ?
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
_geom_hbond_publ_flag
N1 H1 O4 3 0.86 2.21 2.968(4) 147 y
C17 H17A O4 . 0.96 2.39 3.016(5) 123 y
C20 H20 O1 . 0.98 2.44 3.126(4) 126 y
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
C8 N1 C2 O1 . . . . 174.9(3) ?
C8 N1 C2 C3 . . . . -5.3(4) ?
O1 C2 C3 C9 . . . . -173.3(3) ?
N1 C2 C3 C9 . . . . 7.0(3) ?
O1 C2 C3 C10 . . . . -50.0(4) ?
N1 C2 C3 C10 . . . . 130.2(3) ?
O1 C2 C3 C21 . . . . 65.1(4) ?
N1 C2 C3 C21 . . . . -114.6(3) ?
C9 C4 C5 C6 . . . . 0.3(5) ?
C26 O2 C6 C7 . . . . -66.8(4) ?
C26 O2 C6 C5 . . . . 116.4(3) ?
C4 C5 C6 O2 . . . . 178.3(3) ?
C4 C5 C6 C7 . . . . 1.4(5) ?
O2 C6 C7 C8 . . . . -177.3(3) ?
C5 C6 C7 C8 . . . . -0.5(5) ?
O2 C6 C7 O3 . . . . -0.9(5) ?
C5 C6 C7 O3 . . . . 175.9(3) ?
C24 O3 C7 C8 . . . . -141.1(3) ?
C24 O3 C7 C6 . . . . 42.5(5) ?
C6 C7 C8 C9 . . . . -2.2(5) ?
O3 C7 C8 C9 . . . . -178.8(3) ?
C6 C7 C8 N1 . . . . 178.3(3) ?
O3 C7 C8 N1 . . . . 1.6(5) ?
C2 N1 C8 C7 . . . . -179.3(3) ?
C2 N1 C8 C9 . . . . 1.1(4) ?
C5 C4 C9 C8 . . . . -2.9(5) ?
C5 C4 C9 C3 . . . . 176.9(3) ?
C7 C8 C9 C4 . . . . 3.9(5) ?
N1 C8 C9 C4 . . . . -176.5(3) ?
C7 C8 C9 C3 . . . . -175.9(3) ?
N1 C8 C9 C3 . . . . 3.7(4) ?
C2 C3 C9 C4 . . . . 173.8(3) ?
C10 C3 C9 C4 . . . . 55.7(5) ?
C21 C3 C9 C4 . . . . -67.8(5) ?
C2 C3 C9 C8 . . . . -6.3(3) ?
C10 C3 C9 C8 . . . . -124.5(3) ?
C21 C3 C9 C8 . . . . 112.1(3) ?
C9 C3 C10 C11 . . . . -146.2(3) ?
C2 C3 C10 C11 . . . . 100.4(3) ?
C21 C3 C10 C11 . . . . -18.0(3) ?
C18 N3 C11 C10 . . . . 172.4(3) ?
C29 N3 C11 C10 . . . . -6.6(5) ?
C18 N3 C11 C12 . . . . -64.0(3) ?
C29 N3 C11 C12 . . . . 117.0(4) ?
C18 N3 C11 C20 . . . . 57.0(3) ?
C29 N3 C11 C20 . . . . -122.0(4) ?
C3 C10 C11 N3 . . . . -121.9(3) ?
C3 C10 C11 C12 . . . . 118.4(3) ?
C3 C10 C11 C20 . . . . -6.5(3) ?
C16 N2 C12 C11 . . . . -124.8(3) ?
C13 N2 C12 C11 . . . . -1.1(4) ?
N3 C11 C12 N2 . . . . 59.7(3) ?
C10 C11 C12 N2 . . . . -172.8(3) ?
C20 C11 C12 N2 . . . . -53.9(4) ?
C16 N2 C13 C14 . . . . -46.9(4) ?
C12 N2 C13 C14 . . . . -176.3(3) ?
C16 N2 C13 C19 . . . . -168.3(3) ?
C12 N2 C13 C19 . . . . 62.3(4) ?
C16 N2 C13 C18 . . . . 73.7(4) ?
C12 N2 C13 C18 . . . . -55.7(3) ?
N2 C13 C14 C17 . . . . 167.8(4) ?
C19 C13 C14 C17 . . . . -77.6(5) ?
C18 C13 C14 C17 . . . . 53.5(5) ?
N2 C13 C14 C15 . . . . 40.5(4) ?
C19 C13 C14 C15 . . . . 155.1(3) ?
C18 C13 C14 C15 . . . . -73.7(4) ?
C17 C14 C15 C16 . . . . -152.3(4) ?
C13 C14 C15 C16 . . . . -21.5(5) ?
C12 N2 C16 C15 . . . . 160.1(3) ?
C13 N2 C16 C15 . . . . 33.2(4) ?
C14 C15 C16 N2 . . . . -6.0(5) ?
C29 N3 C18 O4 . . . . 1.6(5) ?
C11 N3 C18 O4 . . . . -177.4(3) ?
C29 N3 C18 C13 . . . . -174.5(3) ?
C11 N3 C18 C13 . . . . 6.5(4) ?
N2 C13 C18 O4 . . . . -121.8(4) ?
C14 C13 C18 O4 . . . . -11.4(5) ?
C19 C13 C18 O4 . . . . 122.4(4) ?
N2 C13 C18 N3 . . . . 54.3(3) ?
C14 C13 C18 N3 . . . . 164.6(3) ?
C19 C13 C18 N3 . . . . -61.5(4) ?
N2 C13 C19 C20 . . . . -70.9(3) ?
C14 C13 C19 C20 . . . . 178.3(3) ?
C18 C13 C19 C20 . . . . 44.8(4) ?
C13 C19 C20 C11 . . . . 17.3(4) ?
C13 C19 C20 C21 . . . . 144.4(3) ?
N3 C11 C20 C19 . . . . -69.8(3) ?
C10 C11 C20 C19 . . . . 166.1(3) ?
C12 C11 C20 C19 . . . . 43.4(4) ?
N3 C11 C20 C21 . . . . 154.0(3) ?
C10 C11 C20 C21 . . . . 29.8(3) ?
C12 C11 C20 C21 . . . . -92.8(3) ?
C19 C20 C21 C23 . . . . 73.5(4) ?
C11 C20 C21 C23 . . . . -158.6(3) ?
C19 C20 C21 C22 . . . . -48.1(4) ?
C11 C20 C21 C22 . . . . 79.8(3) ?
C19 C20 C21 C3 . . . . -167.6(3) ?
C11 C20 C21 C3 . . . . -39.7(3) ?
C9 C3 C21 C23 . . . . -77.2(4) ?
C2 C3 C21 C23 . . . . 35.6(4) ?
C10 C3 C21 C23 . . . . 153.4(3) ?
C9 C3 C21 C20 . . . . 163.9(3) ?
C2 C3 C21 C20 . . . . -83.2(3) ?
C10 C3 C21 C20 . . . . 34.5(3) ?
C9 C3 C21 C22 . . . . 43.6(4) ?
C2 C3 C21 C22 . . . . 156.5(3) ?
C10 C3 C21 C22 . . . . -85.8(3) ?
C7 O3 C24 C25 . . . . -20.7(6) ?
O3 C24 C25 C26 . . . . -3.5(7) ?
C6 O2 C26 C25 . . . . 71.2(4) ?
C6 O2 C26 C28 . . . . -51.3(4) ?
C6 O2 C26 C27 . . . . -170.3(3) ?
C24 C25 C26 O2 . . . . -23.2(6) ?
C24 C25 C26 C28 . . . . 98.6(5) ?
C24 C25 C26 C27 . . . . -137.2(5) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24745716
2 PubChem 133562749
