#------------------------------------------------------------------------------
#$Date: 2025-08-19 16:18:28 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301805 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/67/2226788.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_2226788
loop_
_publ_author_name
'Chantrapromma, Suchada'
'Boonnak, Nawong'
'Fun, Hoong-Kun'
'Karalai, Chatchanok'
'Chantrapromma, Kan'
_publ_section_title
;
 Brasilixanthone
;
_journal_coeditor_code           BT5295
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2066
_journal_page_last               o2067
_journal_paper_doi               10.1107/S1600536810027285
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C23 H20 O6'
_chemical_formula_moiety         'C23 H20 O6'
_chemical_formula_sum            'C23 H20 O6'
_chemical_formula_weight         392.39
_chemical_melting_point_gt       478
_chemical_melting_point_lt       480
_chemical_name_common
;
Brasilixanthone
;
_chemical_name_systematic
;
5,13-dihydroxy-3,3,10,10-tetramethyl-3H-
dipyrano[3,2-a:2',3'-i]xanthen-14(10H)-one
;
_space_group_IT_number           7
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P -2yc'
_symmetry_space_group_name_H-M   'P 1 c 1'
_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                 96.827(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.5842(3)
_cell_length_b                   12.2937(4)
_cell_length_c                   19.6023(6)
_cell_measurement_reflns_used    3554
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.00
_cell_measurement_theta_min      1.96
_cell_volume                     1814.72(11)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0765
_diffrn_reflns_av_sigmaI/netI    0.0365
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            33718
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.96
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.9931
_exptl_absorpt_correction_T_min  0.9629
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.07
_refine_diff_density_max         1.214
_refine_diff_density_min         -0.390
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     453
_refine_ls_number_reflns         3554
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.1162
_refine_ls_R_factor_gt           0.1026
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1648P)²+5.5181P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2548
_refine_ls_wR_factor_ref         0.2702
_reflns_number_gt                2954
_reflns_number_total             3554
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt5295.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P c'
_cod_database_code               2226788
_cod_database_fobs_code          2226788
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
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
O O1A 0.2594(8) 0.6225(5) 0.5423(3) 0.0284(14) Uani d . 1 . .
O O2A 0.7864(8) 0.5793(5) 0.6095(4) 0.0300(15) Uani d . 1 . .
O O3A 0.7794(8) 0.7513(5) 0.6837(3) 0.0299(15) Uani d . 1 . .
H H3AA 0.8227 0.6975 0.6674 0.045 Uiso calc R 1 . .
O O4A 0.5559(8) 0.2608(5) 0.4390(3) 0.0254(13) Uani d . 1 . .
O O5A 0.2102(8) 0.3007(5) 0.4131(3) 0.0289(14) Uani d . 1 . .
H H5AA 0.2715 0.2500 0.4024 0.043 Uiso calc R 1 . .
O O6A 0.2246(8) 0.9394(5) 0.6739(3) 0.0256(14) Uani d . 1 . .
C C1A 0.6044(13) 0.4207(7) 0.5107(5) 0.0251(19) Uani d . 1 . .
C C2A 0.4941(11) 0.3517(7) 0.4674(4) 0.0219(6) Uani d . 1 . .
C C3A 0.3142(12) 0.3725(7) 0.4539(4) 0.0252(18) Uani d . 1 . .
C C4A 0.2407(11) 0.4679(7) 0.4795(4) 0.0219(6) Uani d . 1 . .
H H4AA 0.1211 0.4849 0.4685 0.026 Uiso calc R 1 . .
C C5A 0.2460(11) 0.7814(7) 0.6065(5) 0.0254(18) Uani d . 1 . .
H H5AB 0.1273 0.7895 0.5889 0.031 Uiso calc R 1 . .
C C6A 0.3293(13) 0.8539(7) 0.6537(4) 0.0275(14) Uani d . 1 . .
C C7A 0.5028(12) 0.8473(7) 0.6790(5) 0.029(2) Uani d . 1 . .
C C8A 0.6086(12) 0.7602(8) 0.6578(5) 0.030(2) Uani d . 1 . .
C C9A 0.6311(12) 0.5885(8) 0.5873(4) 0.028(2) Uani d . 1 . .
C C10A 0.5222(12) 0.5135(7) 0.5380(5) 0.028(2) Uani d . 1 . .
C C11A 0.3485(13) 0.5325(7) 0.5197(5) 0.0271(19) Uani d . 1 . .
C C12A 0.3513(13) 0.6930(8) 0.5859(4) 0.0275(14) Uani d . 1 . .
C C13A 0.5217(13) 0.6810(8) 0.6099(5) 0.029(2) Uani d . 1 . .
C C14A 0.7423(11) 0.2633(7) 0.4260(5) 0.0219(6) Uani d . 1 . .
C C15A 0.8475(12) 0.3104(7) 0.4909(5) 0.0244(13) Uani d . 1 . .
H H15A 0.9617 0.2847 0.5042 0.029 Uiso calc R 1 . .
C C16A 0.7838(12) 0.3844(7) 0.5280(4) 0.0244(13) Uani d . 1 . .
H H16A 0.8539 0.4139 0.5656 0.029 Uiso calc R 1 . .
C C17A 0.7541(11) 0.3372(7) 0.3641(4) 0.0235(17) Uani d . 1 . .
H H17A 0.6762 0.3105 0.3256 0.035 Uiso calc R 1 . .
H H17B 0.8739 0.3378 0.3529 0.035 Uiso calc R 1 . .
H H17C 0.7197 0.4097 0.3750 0.035 Uiso calc R 1 . .
C C18A 0.7952(13) 0.1488(7) 0.4115(5) 0.031(2) Uani d . 1 . .
H H18A 0.7115 0.1184 0.3760 0.047 Uiso calc R 1 . .
H H18B 0.7965 0.1059 0.4525 0.047 Uiso calc R 1 . .
H H18C 0.9115 0.1487 0.3968 0.047 Uiso calc R 1 . .
C C19A 0.2789(11) 0.9818(7) 0.7425(4) 0.0219(6) Uani d . 1 . .
C C20A 0.4757(11) 0.9990(8) 0.7499(4) 0.0219(6) Uani d . 1 . .
H H20A 0.5231 1.0607 0.7725 0.026 Uiso calc R 1 . .
C C21A 0.5832(12) 0.9296(7) 0.7253(5) 0.0269(19) Uani d . 1 . .
H H21A 0.7055 0.9332 0.7372 0.032 Uiso calc R 1 . .
C C22A 0.2221(11) 0.9032(7) 0.7950(4) 0.0219(6) Uani d . 1 . .
H H22A 0.2928 0.8383 0.7954 0.033 Uiso calc R 1 . .
H H22B 0.0992 0.8849 0.7832 0.033 Uiso calc R 1 . .
H H22C 0.2384 0.9363 0.8396 0.033 Uiso calc R 1 . .
C C23A 0.1815(13) 1.0908(8) 0.7424(5) 0.030(2) Uani d . 1 . .
H H23A 0.2025 1.1318 0.7025 0.046 Uiso calc R 1 . .
H H23B 0.2245 1.1310 0.7830 0.046 Uiso calc R 1 . .
H H23C 0.0564 1.0781 0.7417 0.046 Uiso calc R 1 . .
O O1B 0.7714(6) 0.1279(5) 0.6348(3) 0.0170(11) Uani d . 1 . .
O O2B 0.2460(7) 0.1655(5) 0.5601(3) 0.0224(13) Uani d . 1 . .
O O3B 0.2679(7) -0.0013(5) 0.4835(3) 0.0243(14) Uani d . 1 . .
H H3BA 0.2190 0.0505 0.4997 0.036 Uiso calc R 1 . .
O O4B 0.4578(7) 0.4885(5) 0.7314(3) 0.0234(13) Uani d . 1 . .
O O5B 0.7974(7) 0.4482(5) 0.7649(3) 0.0265(14) Uani d . 1 . .
H H5BA 0.7316 0.4976 0.7742 0.032 Uiso calc R 1 . .
O O6B 0.8254(8) -0.1813(5) 0.5014(3) 0.0230(13) Uani d . 1 . .
C C1B 0.4180(11) 0.3280(7) 0.6589(4) 0.0219(6) Uani d . 1 . .
C C2B 0.5194(11) 0.3932(7) 0.7039(4) 0.0219(6) Uani d . 1 . .
C C3B 0.7035(11) 0.3754(7) 0.7233(4) 0.0195(16) Uani d . 1 . .
C C4B 0.7810(10) 0.2841(7) 0.6989(4) 0.0186(16) Uani d . 1 . .
H H4BA 0.9004 0.2689 0.7120 0.022 Uiso calc R 1 . .
C C5B 0.7971(10) -0.0268(6) 0.5681(4) 0.0168(9) Uani d . 1 . .
H H5BB 0.9150 -0.0335 0.5871 0.020 Uiso calc R 1 . .
C C6B 0.7222(10) -0.1000(7) 0.5196(4) 0.0168(9) Uani d . 1 . .
C C7B 0.5435(10) -0.0911(6) 0.4902(4) 0.0177(11) Uani d . 1 . .
C C8B 0.4416(10) -0.0059(6) 0.5117(4) 0.0139(15) Uani d . 1 . .
C C9B 0.4054(10) 0.1592(6) 0.5834(4) 0.0155(15) Uani d . 1 . .
C C10B 0.4968(9) 0.2335(7) 0.6322(4) 0.0158(16) Uani d . 1 . .
C C11B 0.6794(10) 0.2163(7) 0.6551(4) 0.0168(9) Uani d . 1 . .
C C12B 0.6909(11) 0.0571(6) 0.5876(4) 0.0177(11) Uani d . 1 . .
C C13B 0.5122(10) 0.0696(7) 0.5609(4) 0.0161(16) Uani d . 1 . .
C C14B 0.2689(10) 0.4816(6) 0.7418(4) 0.0145(15) Uani d . 1 . .
C C15B 0.1709(11) 0.4396(7) 0.6785(4) 0.0188(16) Uani d . 1 . .
H H15B 0.0594 0.4685 0.6640 0.023 Uiso calc R 1 . .
C C16B 0.2338(10) 0.3616(7) 0.6407(4) 0.0201(17) Uani d . 1 . .
H H16B 0.1629 0.3299 0.6041 0.024 Uiso calc R 1 . .
C C17B 0.2476(11) 0.4105(7) 0.8039(4) 0.0213(13) Uani d . 1 . .
H H17D 0.3047 0.3417 0.7990 0.032 Uiso calc R 1 . .
H H17E 0.1236 0.3989 0.8069 0.032 Uiso calc R 1 . .
H H17F 0.3009 0.4459 0.8448 0.032 Uiso calc R 1 . .
C C18B 0.2195(11) 0.6005(7) 0.7543(4) 0.0213(13) Uani d . 1 . .
H H18D 0.2315 0.6426 0.7139 0.032 Uiso calc R 1 . .
H H18E 0.2972 0.6291 0.7923 0.032 Uiso calc R 1 . .
H H18F 0.0990 0.6040 0.7645 0.032 Uiso calc R 1 . .
C C19B 0.7833(11) -0.2314(7) 0.4314(4) 0.0216(18) Uani d . 1 . .
C C20B 0.5868(11) -0.2446(7) 0.4176(5) 0.0244(18) Uani d . 1 . .
H H20B 0.5415 -0.3022 0.3901 0.029 Uiso calc R 1 . .
C C21B 0.4738(10) -0.1771(7) 0.4431(5) 0.0240(18) Uani d . 1 . .
H H21B 0.3520 -0.1846 0.4311 0.029 Uiso calc R 1 . .
C C22B 0.8534(13) -0.1520(8) 0.3810(5) 0.034(2) Uani d . 1 . .
H H22D 0.9794 -0.1439 0.3921 0.050 Uiso calc R 1 . .
H H22E 0.7969 -0.0826 0.3842 0.050 Uiso calc R 1 . .
H H22F 0.8279 -0.1797 0.3351 0.050 Uiso calc R 1 . .
C C23B 0.8837(12) -0.3365(7) 0.4352(5) 0.028(2) Uani d . 1 . .
H H23D 1.0078 -0.3223 0.4477 0.042 Uiso calc R 1 . .
H H23E 0.8670 -0.3718 0.3912 0.042 Uiso calc R 1 . .
H H23F 0.8408 -0.3828 0.4690 0.042 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 0.0000 '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 0.0000 '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
C12A O1A C11A . . 118.5(7) ?
C8A O3A H3AA . . 109.5 ?
C2A O4A C14A . . 116.2(6) ?
C3A O5A H5AA . . 109.5 ?
C6A O6A C19A . . 115.0(7) ?
C2A C1A C16A . . 115.8(8) ?
C2A C1A C10A . . 116.9(9) ?
C16A C1A C10A . . 127.0(9) ?
O4A C2A C3A . . 117.1(8) ?
O4A C2A C1A . . 122.4(8) ?
C3A C2A C1A . . 120.5(8) ?
O5A C3A C2A . . 118.5(8) ?
O5A C3A C4A . . 121.0(8) ?
C2A C3A C4A . . 120.5(8) ?
C11A C4A C3A . . 117.7(8) ?
C11A C4A H4AA . . 121.2 ?
C3A C4A H4AA . . 121.2 ?
C6A C5A C12A . . 116.8(8) ?
C6A C5A H5AB . . 121.6 ?
C12A C5A H5AB . . 121.6 ?
C7A C6A C5A . . 123.6(9) ?
C7A C6A O6A . . 120.0(8) ?
C5A C6A O6A . . 116.3(8) ?
C6A C7A C8A . . 119.6(9) ?
C6A C7A C21A . . 120.5(8) ?
C8A C7A C21A . . 119.9(8) ?
O3A C8A C7A . . 120.2(8) ?
O3A C8A C13A . . 122.2(9) ?
C7A C8A C13A . . 117.5(9) ?
O2A C9A C13A . . 120.7(8) ?
O2A C9A C10A . . 127.5(9) ?
C13A C9A C10A . . 111.8(8) ?
C11A C10A C1A . . 119.7(10) ?
C11A C10A C9A . . 120.6(8) ?
C1A C10A C9A . . 119.7(8) ?
C4A C11A C10A . . 124.6(9) ?
C4A C11A O1A . . 112.0(8) ?
C10A C11A O1A . . 123.3(9) ?
C13A C12A O1A . . 124.0(9) ?
C13A C12A C5A . . 122.3(8) ?
O1A C12A C5A . . 113.7(8) ?
C12A C13A C8A . . 120.0(9) ?
C12A C13A C9A . . 121.7(9) ?
C8A C13A C9A . . 118.2(8) ?
O4A C14A C18A . . 107.3(7) ?
O4A C14A C17A . . 107.4(7) ?
C18A C14A C17A . . 111.4(7) ?
O4A C14A C15A . . 106.3(7) ?
C18A C14A C15A . . 112.8(8) ?
C17A C14A C15A . . 111.2(7) ?
C16A C15A C14A . . 122.7(9) ?
C16A C15A H15A . . 118.7 ?
C14A C15A H15A . . 118.7 ?
C15A C16A C1A . . 119.6(8) ?
C15A C16A H16A . . 120.2 ?
C1A C16A H16A . . 120.2 ?
C14A C17A H17A . . 109.5 ?
C14A C17A H17B . . 109.5 ?
H17A C17A H17B . . 109.5 ?
C14A C17A H17C . . 109.5 ?
H17A C17A H17C . . 109.5 ?
H17B C17A H17C . . 109.5 ?
C14A C18A H18A . . 109.5 ?
C14A C18A H18B . . 109.5 ?
H18A C18A H18B . . 109.5 ?
C14A C18A H18C . . 109.5 ?
H18A C18A H18C . . 109.5 ?
H18B C18A H18C . . 109.5 ?
O6A C19A C20A . . 108.0(6) ?
O6A C19A C22A . . 109.1(7) ?
C20A C19A C22A . . 112.7(7) ?
O6A C19A C23A . . 103.3(7) ?
C20A C19A C23A . . 110.6(8) ?
C22A C19A C23A . . 112.6(7) ?
C21A C20A C19A . . 122.0(9) ?
C21A C20A H20A . . 119.0 ?
C19A C20A H20A . . 119.0 ?
C20A C21A C7A . . 116.9(9) ?
C20A C21A H21A . . 121.6 ?
C7A C21A H21A . . 121.6 ?
C19A C22A H22A . . 109.5 ?
C19A C22A H22B . . 109.5 ?
H22A C22A H22B . . 109.5 ?
C19A C22A H22C . . 109.5 ?
H22A C22A H22C . . 109.5 ?
H22B C22A H22C . . 109.5 ?
C19A C23A H23A . . 109.5 ?
C19A C23A H23B . . 109.5 ?
H23A C23A H23B . . 109.5 ?
C19A C23A H23C . . 109.5 ?
H23A C23A H23C . . 109.5 ?
H23B C23A H23C . . 109.5 ?
C12B O1B C11B . . 120.0(6) ?
C8B O3B H3BA . . 109.5 ?
C2B O4B C14B . . 112.4(6) ?
C3B O5B H5BA . . 109.5 ?
C6B O6B C19B . . 118.6(6) ?
C2B C1B C10B . . 119.1(8) ?
C2B C1B C16B . . 116.3(8) ?
C10B C1B C16B . . 124.6(8) ?
C1B C2B O4B . . 123.8(8) ?
C1B C2B C3B . . 123.0(8) ?
O4B C2B C3B . . 113.0(7) ?
O5B C3B C4B . . 122.1(7) ?
O5B C3B C2B . . 119.2(7) ?
C4B C3B C2B . . 118.6(8) ?
C11B C4B C3B . . 118.9(7) ?
C11B C4B H4BA . . 120.6 ?
C3B C4B H4BA . . 120.6 ?
C6B C5B C12B . . 117.9(7) ?
C6B C5B H5BB . . 121.1 ?
C12B C5B H5BB . . 121.1 ?
O6B C6B C5B . . 117.5(7) ?
O6B C6B C7B . . 120.7(7) ?
C5B C6B C7B . . 121.8(7) ?
C8B C7B C6B . . 118.3(7) ?
C8B C7B C21B . . 124.2(7) ?
C6B C7B C21B . . 117.3(7) ?
O3B C8B C7B . . 116.7(7) ?
O3B C8B C13B . . 121.5(6) ?
C7B C8B C13B . . 121.7(7) ?
O2B C9B C10B . . 125.2(7) ?
O2B C9B C13B . . 118.9(7) ?
C10B C9B C13B . . 115.9(7) ?
C11B C10B C1B . . 116.0(7) ?
C11B C10B C9B . . 119.4(7) ?
C1B C10B C9B . . 124.6(7) ?
C4B C11B O1B . . 113.3(7) ?
C4B C11B C10B . . 124.3(7) ?
O1B C11B C10B . . 122.4(7) ?
O1B C12B C5B . . 115.7(7) ?
O1B C12B C13B . . 121.2(7) ?
C5B C12B C13B . . 123.0(7) ?
C8B C13B C12B . . 117.3(7) ?
C8B C13B C9B . . 121.7(7) ?
C12B C13B C9B . . 121.0(7) ?
C15B C14B O4B . . 107.9(6) ?
C15B C14B C17B . . 112.5(7) ?
O4B C14B C17B . . 110.0(6) ?
C15B C14B C18B . . 111.2(7) ?
O4B C14B C18B . . 103.1(6) ?
C17B C14B C18B . . 111.6(6) ?
C16B C15B C14B . . 123.1(7) ?
C16B C15B H15B . . 118.5 ?
C14B C15B H15B . . 118.5 ?
C15B C16B C1B . . 117.5(8) ?
C15B C16B H16B . . 121.2 ?
C1B C16B H16B . . 121.2 ?
C14B C17B H17D . . 109.5 ?
C14B C17B H17E . . 109.5 ?
H17D C17B H17E . . 109.5 ?
C14B C17B H17F . . 109.5 ?
H17D C17B H17F . . 109.5 ?
H17E C17B H17F . . 109.5 ?
C14B C18B H18D . . 109.5 ?
C14B C18B H18E . . 109.5 ?
H18D C18B H18E . . 109.5 ?
C14B C18B H18F . . 109.5 ?
H18D C18B H18F . . 109.5 ?
H18E C18B H18F . . 109.5 ?
C20B C19B C23B . . 114.0(8) ?
C20B C19B O6B . . 108.1(6) ?
C23B C19B O6B . . 104.9(7) ?
C20B C19B C22B . . 111.7(7) ?
C23B C19B C22B . . 111.6(7) ?
O6B C19B C22B . . 106.0(7) ?
C21B C20B C19B . . 122.5(7) ?
C21B C20B H20B . . 118.8 ?
C19B C20B H20B . . 118.8 ?
C20B C21B C7B . . 119.2(7) ?
C20B C21B H21B . . 120.4 ?
C7B C21B H21B . . 120.4 ?
C19B C22B H22D . . 109.5 ?
C19B C22B H22E . . 109.5 ?
H22D C22B H22E . . 109.5 ?
C19B C22B H22F . . 109.5 ?
H22D C22B H22F . . 109.5 ?
H22E C22B H22F . . 109.5 ?
C19B C23B H23D . . 109.5 ?
C19B C23B H23E . . 109.5 ?
H23D C23B H23E . . 109.5 ?
C19B C23B H23F . . 109.5 ?
H23D C23B H23F . . 109.5 ?
H23E C23B H23F . . 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
O1A C12A . 1.351(11) ?
O1A C11A . 1.395(11) ?
O2A C9A . 1.211(11) ?
O3A C8A . 1.338(11) ?
O3A H3AA . 0.8200 ?
O4A C2A . 1.356(10) ?
O4A C14A . 1.467(10) ?
O5A C3A . 1.376(10) ?
O5A H5AA . 0.8200 ?
O6A C6A . 1.402(11) ?
O6A C19A . 1.455(11) ?
C1A C2A . 1.405(13) ?
C1A C16A . 1.433(14) ?
C1A C10A . 1.434(12) ?
C2A C3A . 1.382(12) ?
C3A C4A . 1.416(12) ?
C4A C11A . 1.330(13) ?
C4A H4AA . 0.9300 ?
C5A C6A . 1.382(12) ?
C5A C12A . 1.434(12) ?
C5A H5AB . 0.9300 ?
C6A C7A . 1.352(14) ?
C7A C8A . 1.429(13) ?
C7A C21A . 1.446(14) ?
C8A C13A . 1.454(13) ?
C9A C13A . 1.505(13) ?
C9A C10A . 1.508(13) ?
C10A C11A . 1.344(14) ?
C12A C13A . 1.331(14) ?
C14A C18A . 1.501(12) ?
C14A C17A . 1.527(12) ?
C14A C15A . 1.532(12) ?
C15A C16A . 1.293(13) ?
C15A H15A . 0.9300 ?
C16A H16A . 0.9300 ?
C17A H17A . 0.9600 ?
C17A H17B . 0.9600 ?
C17A H17C . 0.9600 ?
C18A H18A . 0.9600 ?
C18A H18B . 0.9600 ?
C18A H18C . 0.9600 ?
C19A C20A . 1.498(11) ?
C19A C22A . 1.511(11) ?
C19A C23A . 1.530(12) ?
C20A C21A . 1.309(12) ?
C20A H20A . 0.9300 ?
C21A H21A . 0.9300 ?
C22A H22A . 0.9600 ?
C22A H22B . 0.9600 ?
C22A H22C . 0.9600 ?
C23A H23A . 0.9600 ?
C23A H23B . 0.9600 ?
C23A H23C . 0.9600 ?
O1B C12B . 1.361(9) ?
O1B C11B . 1.375(9) ?
O2B C9B . 1.242(9) ?
O3B C8B . 1.368(9) ?
O3B H3BA . 0.8200 ?
O4B C2B . 1.393(10) ?
O4B C14B . 1.473(9) ?
O5B C3B . 1.355(10) ?
O5B H5BA . 0.8200 ?
O6B C6B . 1.343(9) ?
O6B C19B . 1.503(9) ?
C1B C2B . 1.361(13) ?
C1B C10B . 1.434(11) ?
C1B C16B . 1.460(11) ?
C2B C3B . 1.420(12) ?
C3B C4B . 1.379(11) ?
C4B C11B . 1.367(12) ?
C4B H4BA . 0.9300 ?
C5B C6B . 1.382(11) ?
C5B C12B . 1.390(10) ?
C5B H5BB . 0.9300 ?
C6B C7B . 1.412(11) ?
C7B C8B . 1.397(10) ?
C7B C21B . 1.461(11) ?
C8B C13B . 1.398(11) ?
C9B C10B . 1.439(11) ?
C9B C13B . 1.466(10) ?
C10B C11B . 1.420(10) ?
C12B C13B . 1.402(11) ?
C14B C15B . 1.463(11) ?
C14B C17B . 1.522(11) ?
C14B C18B . 1.535(10) ?
C15B C16B . 1.334(11) ?
C15B H15B . 0.9300 ?
C16B H16B . 0.9300 ?
C17B H17D . 0.9600 ?
C17B H17E . 0.9600 ?
C17B H17F . 0.9600 ?
C18B H18D . 0.9600 ?
C18B H18E . 0.9600 ?
C18B H18F . 0.9600 ?
C19B C20B . 1.491(11) ?
C19B C23B . 1.497(11) ?
C19B C22B . 1.528(13) ?
C20B C21B . 1.333(12) ?
C20B H20B . 0.9300 ?
C21B H21B . 0.9300 ?
C22B H22D . 0.9600 ?
C22B H22E . 0.9600 ?
C22B H22F . 0.9600 ?
C23B H23D . 0.9600 ?
C23B H23E . 0.9600 ?
C23B H23F . 0.9600 ?
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
O3A H3AA O2A 1_555 0.82 1.84 2.571(9) 147 y
O5A H5AA O4A 1_555 0.82 2.19 2.656(9) 116 y
O3B H3BA O2B 1_555 0.82 1.84 2.559(9) 146 y
O5B H5BA O4B 1_555 0.82 2.15 2.628(8) 117 y
C15B H15B O2A 1_455 0.93 2.60 3.514(11) 168 y
C16A H16A O2A 1_555 0.93 2.29 2.879(11) 121 y
C16B H16B O2B 1_555 0.93 2.31 2.890(10) 120 y
C17B H17E O5B 1_455 0.96 2.58 3.441(10) 149 y
C23B H23D O1A 1_645 0.96 2.59 3.370(11) 139 y
C18A H18B Cg20 1_555 0.96 2.75 3.611(10) 150 y
C18B H18D Cg5 1_555 0.96 2.79 3.662(9) 152 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
C14A O4A C2A C3A . . . . 153.0(7) ?
C14A O4A C2A C1A . . . . -29.3(11) ?
C16A C1A C2A O4A . . . . -5.1(12) ?
C10A C1A C2A O4A . . . . -179.3(7) ?
C16A C1A C2A C3A . . . . 172.5(7) ?
C10A C1A C2A C3A . . . . -1.7(12) ?
O4A C2A C3A O5A . . . . 0.0(11) ?
C1A C2A C3A O5A . . . . -177.7(7) ?
O4A C2A C3A C4A . . . . -177.6(7) ?
C1A C2A C3A C4A . . . . 4.7(12) ?
O5A C3A C4A C11A . . . . 178.7(7) ?
C2A C3A C4A C11A . . . . -3.8(12) ?
C12A C5A C6A C7A . . . . 2.1(13) ?
C12A C5A C6A O6A . . . . -179.4(7) ?
C19A O6A C6A C7A . . . . -29.2(11) ?
C19A O6A C6A C5A . . . . 152.2(7) ?
C5A C6A C7A C8A . . . . -1.2(13) ?
O6A C6A C7A C8A . . . . -179.6(7) ?
C5A C6A C7A C21A . . . . 176.5(8) ?
O6A C6A C7A C21A . . . . -1.9(12) ?
C6A C7A C8A O3A . . . . -178.4(8) ?
C21A C7A C8A O3A . . . . 3.8(12) ?
C6A C7A C8A C13A . . . . -0.9(12) ?
C21A C7A C8A C13A . . . . -178.7(7) ?
C2A C1A C10A C11A . . . . -2.1(12) ?
C16A C1A C10A C11A . . . . -175.6(8) ?
C2A C1A C10A C9A . . . . 177.4(7) ?
C16A C1A C10A C9A . . . . 4.0(13) ?
O2A C9A C10A C11A . . . . 177.6(9) ?
C13A C9A C10A C11A . . . . -0.6(11) ?
O2A C9A C10A C1A . . . . -1.9(13) ?
C13A C9A C10A C1A . . . . 179.8(7) ?
C3A C4A C11A C10A . . . . -0.2(13) ?
C3A C4A C11A O1A . . . . -179.0(7) ?
C1A C10A C11A C4A . . . . 3.1(13) ?
C9A C10A C11A C4A . . . . -176.4(8) ?
C1A C10A C11A O1A . . . . -178.1(7) ?
C9A C10A C11A O1A . . . . 2.3(12) ?
C12A O1A C11A C4A . . . . 177.5(7) ?
C12A O1A C11A C10A . . . . -1.4(12) ?
C11A O1A C12A C13A . . . . -1.4(12) ?
C11A O1A C12A C5A . . . . -179.1(7) ?
C6A C5A C12A C13A . . . . -0.8(13) ?
C6A C5A C12A O1A . . . . 177.0(7) ?
O1A C12A C13A C8A . . . . -178.8(8) ?
C5A C12A C13A C8A . . . . -1.3(13) ?
O1A C12A C13A C9A . . . . 3.1(14) ?
C5A C12A C13A C9A . . . . -179.3(7) ?
O3A C8A C13A C12A . . . . 179.6(8) ?
C7A C8A C13A C12A . . . . 2.2(13) ?
O3A C8A C13A C9A . . . . -2.3(13) ?
C7A C8A C13A C9A . . . . -179.7(7) ?
O2A C9A C13A C12A . . . . 179.6(8) ?
C10A C9A C13A C12A . . . . -2.0(12) ?
O2A C9A C13A C8A . . . . 1.5(12) ?
C10A C9A C13A C8A . . . . 179.9(7) ?
C2A O4A C14A C18A . . . . 166.4(7) ?
C2A O4A C14A C17A . . . . -73.7(9) ?
C2A O4A C14A C15A . . . . 45.5(9) ?
O4A C14A C15A C16A . . . . -34.4(11) ?
C18A C14A C15A C16A . . . . -151.7(8) ?
C17A C14A C15A C16A . . . . 82.2(10) ?
C14A C15A C16A C1A . . . . 3.6(13) ?
C2A C1A C16A C15A . . . . 18.1(12) ?
C10A C1A C16A C15A . . . . -168.4(8) ?
C6A O6A C19A C20A . . . . 46.9(9) ?
C6A O6A C19A C22A . . . . -75.9(8) ?
C6A O6A C19A C23A . . . . 164.1(7) ?
O6A C19A C20A C21A . . . . -40.2(11) ?
C22A C19A C20A C21A . . . . 80.4(10) ?
C23A C19A C20A C21A . . . . -152.6(8) ?
C19A C20A C21A C7A . . . . 12.1(12) ?
C6A C7A C21A C20A . . . . 10.9(12) ?
C8A C7A C21A C20A . . . . -171.4(8) ?
C10B C1B C2B O4B . . . . 178.1(7) ?
C16B C1B C2B O4B . . . . -1.1(12) ?
C10B C1B C2B C3B . . . . 3.3(12) ?
C16B C1B C2B C3B . . . . -175.9(7) ?
C14B O4B C2B C1B . . . . 33.4(11) ?
C14B O4B C2B C3B . . . . -151.3(7) ?
C1B C2B C3B O5B . . . . 175.7(7) ?
O4B C2B C3B O5B . . . . 0.4(11) ?
C1B C2B C3B C4B . . . . -4.2(12) ?
O4B C2B C3B C4B . . . . -179.5(7) ?
O5B C3B C4B C11B . . . . -177.6(7) ?
C2B C3B C4B C11B . . . . 2.3(12) ?
C19B O6B C6B C5B . . . . -153.9(7) ?
C19B O6B C6B C7B . . . . 26.5(11) ?
C12B C5B C6B O6B . . . . -179.6(7) ?
C12B C5B C6B C7B . . . . 0.0(11) ?
O6B C6B C7B C8B . . . . 179.1(7) ?
C5B C6B C7B C8B . . . . -0.5(12) ?
O6B C6B C7B C21B . . . . 3.9(11) ?
C5B C6B C7B C21B . . . . -175.7(7) ?
C6B C7B C8B O3B . . . . -178.4(7) ?
C21B C7B C8B O3B . . . . -3.5(11) ?
C6B C7B C8B C13B . . . . 0.3(11) ?
C21B C7B C8B C13B . . . . 175.1(7) ?
C2B C1B C10B C11B . . . . -0.7(11) ?
C16B C1B C10B C11B . . . . 178.5(7) ?
C2B C1B C10B C9B . . . . -178.7(7) ?
C16B C1B C10B C9B . . . . 0.4(13) ?
O2B C9B C10B C11B . . . . 179.5(7) ?
C13B C9B C10B C11B . . . . 0.0(10) ?
O2B C9B C10B C1B . . . . -2.5(13) ?
C13B C9B C10B C1B . . . . 178.0(7) ?
C3B C4B C11B O1B . . . . -179.6(7) ?
C3B C4B C11B C10B . . . . 0.3(12) ?
C12B O1B C11B C4B . . . . -175.6(7) ?
C12B O1B C11B C10B . . . . 4.6(11) ?
C1B C10B C11B C4B . . . . -1.1(12) ?
C9B C10B C11B C4B . . . . 177.0(7) ?
C1B C10B C11B O1B . . . . 178.7(7) ?
C9B C10B C11B O1B . . . . -3.2(11) ?
C11B O1B C12B C5B . . . . 177.2(6) ?
C11B O1B C12B C13B . . . . -2.7(11) ?
C6B C5B C12B O1B . . . . -179.2(7) ?
C6B C5B C12B C13B . . . . 0.8(12) ?
O3B C8B C13B C12B . . . . 179.0(7) ?
C7B C8B C13B C12B . . . . 0.5(11) ?
O3B C8B C13B C9B . . . . -1.6(11) ?
C7B C8B C13B C9B . . . . 179.8(7) ?
O1B C12B C13B C8B . . . . 178.9(7) ?
C5B C12B C13B C8B . . . . -1.0(11) ?
O1B C12B C13B C9B . . . . -0.5(11) ?
C5B C12B C13B C9B . . . . 179.6(7) ?
O2B C9B C13B C8B . . . . 2.9(11) ?
C10B C9B C13B C8B . . . . -177.6(7) ?
O2B C9B C13B C12B . . . . -177.7(7) ?
C10B C9B C13B C12B . . . . 1.8(11) ?
C2B O4B C14B C15B . . . . -48.5(9) ?
C2B O4B C14B C17B . . . . 74.5(8) ?
C2B O4B C14B C18B . . . . -166.3(7) ?
O4B C14B C15B C16B . . . . 38.8(11) ?
C17B C14B C15B C16B . . . . -82.7(10) ?
C18B C14B C15B C16B . . . . 151.2(8) ?
C14B C15B C16B C1B . . . . -8.3(12) ?
C2B C1B C16B C15B . . . . -12.5(11) ?
C10B C1B C16B C15B . . . . 168.3(8) ?
C6B O6B C19B C20B . . . . -41.9(10) ?
C6B O6B C19B C23B . . . . -163.9(7) ?
C6B O6B C19B C22B . . . . 77.9(8) ?
C23B C19B C20B C21B . . . . 147.1(9) ?
O6B C19B C20B C21B . . . . 30.9(12) ?
C22B C19B C20B C21B . . . . -85.3(11) ?
C19B C20B C21B C7B . . . . -4.3(14) ?
C8B C7B C21B C20B . . . . 169.7(8) ?
C6B C7B C21B C20B . . . . -15.4(12) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139079252
