#------------------------------------------------------------------------------
#$Date: 2025-08-07 04:19:51 +0300 (Thu, 07 Aug 2025) $
#$Revision: 301678 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/25/07/7250787.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_7250787
loop_
_publ_author_name
'Sinthopweha, Wichai'
'Khamto, Nopawit'
'Rithchumpon, Puracheth'
'Meepowpan, Puttinan'
_publ_section_title
;
 Methyl itaconate--anthracene adducts (MIAs) facilitate the enantiomeric
 separation of 1,1′-bi-2-naphthols via thin-layer chromatography
 (TLC) with trends predicted by molecular dynamics simulations
;
_journal_issue                   34
_journal_name_full               'RSC Advances'
_journal_page_first              28063
_journal_page_last               28074
_journal_paper_doi               10.1039/D5RA04790K
_journal_volume                  15
_journal_year                    2025
_chemical_formula_moiety         'C40 H30 O5, H2 O, C2 H2 O'
_chemical_formula_sum            'C42 H34 O7'
_chemical_formula_weight         650.69
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2025-02-13
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2025-02-13 deposited with the CCDC.	2025-07-29 downloaded from the CCDC.
;
_cell_angle_alpha                90.877(3)
_cell_angle_beta                 106.567(3)
_cell_angle_gamma                112.991(3)
_cell_formula_units_Z            2
_cell_length_a                   10.4163(4)
_cell_length_b                   12.2293(4)
_cell_length_c                   15.1051(5)
_cell_measurement_reflns_used    10671
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.2360
_cell_measurement_theta_min      1.8260
_cell_volume                     1680.19(12)
_computing_cell_refinement       'CrysAlisPro 1.171.41.111a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.111a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.111a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.913
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -73.00  -3.00   0.50   11.67    --   -9.75 -41.00  84.00  140
  2  ω    -14.00  12.00   0.50   11.67    --   -9.75  41.00-122.00   52
  3  ω    -50.00 -15.00   0.50   11.67    --    9.83 -41.00  84.00   70
  4  ω     15.00  56.00   0.50   11.67    --    9.83  41.00-122.00   82
  5  ω    -80.00 -43.00   0.50   11.67    --   -9.75 -19.00 -90.00   74
  6  ω    -41.00  16.00   0.50   11.67    --   -9.75 -77.00-150.00  114
  7  ω    -51.00 -25.00   0.50   11.67    --   -9.75 125.00   0.00   52
  8  ω    -46.00  -9.00   0.50   11.67    --   -9.75 -37.00-150.00   74
  9  ω    -73.00 -11.00   0.50   11.67    --   -9.75 -37.00   0.00  124
 10  ω    -40.00  13.00   0.50   11.67    --   -9.75 -77.00 120.00  106
 11  ω    -23.00   2.00   0.50   11.67    --   -9.75 -19.00 -90.00   50
 12  ω    -58.00 -24.00   0.50   11.67    --   -9.75 125.00  30.00   68
 13  ω    -49.00   6.00   0.50   11.67    --    9.83 -37.00 -30.00  110
 14  ω     12.00  39.00   0.50   11.67    --    9.83 -99.00 -60.00   54
 15  ω      2.00  77.00   0.50   11.67    --    9.83  19.00 -60.00  150
 16  ω    -32.00  -2.00   0.50   11.67    --    9.83 119.00  -1.35   60
 17  ω    -32.00   1.00   0.50   11.67    --    9.83 116.00  64.01   66
 18  ω      1.00  38.00   0.50   11.67    --    9.83 -99.00   0.00   74
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0525627000
_diffrn_orient_matrix_UB_12      -0.0124432000
_diffrn_orient_matrix_UB_13      0.0239339000
_diffrn_orient_matrix_UB_21      -0.0173972000
_diffrn_orient_matrix_UB_22      -0.0621809000
_diffrn_orient_matrix_UB_23      -0.0082038000
_diffrn_orient_matrix_UB_31      0.0549028000
_diffrn_orient_matrix_UB_32      0.0056447000
_diffrn_orient_matrix_UB_33      0.0425504000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_av_unetI/netI     0.0532
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.913
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            23741
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.913
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.524
_diffrn_reflns_theta_min         2.148
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.09507
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.111a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_description       block
_exptl_crystal_F_000             684
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.520
_refine_diff_density_min         -0.515
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     447
_refine_ls_number_reflns         7093
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.1094
_refine_ls_R_factor_gt           0.0661
_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)+(0.1033P)²+0.1961P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1817
_refine_ls_wR_factor_ref         0.2087
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4198
_reflns_number_total             7093
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5ra04790k2.cif
_cod_data_source_block           670610_pm_c6_auto
_cod_original_cell_volume        1680.19(11)
_cod_database_code               7250787
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O'
_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   0.996
_shelx_estimated_absorpt_t_min   0.958
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O6(H6A,H6B)
2.b Ternary CH refined with riding coordinates:
 C10(H10), C9(H9)
2.c Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C12(H12A,H12B)
2.d Aromatic/amide H refined with riding coordinates:
 C3'(H3'), C8'(H8'), C8"(H8"), C4'(H4'), C5(H5A), C4(H4), C8(H8), C6"(H6"),
 C5'(H5'), C3"(H3"), C4"(H4"), C1(H1), C6'(H6'), C6(H6), C2(H2), C7(H7), C3(H3),
  C7"(H7"), C19(H19), C20(H20), C18(H18), C17(H17)
2.e Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
2.f Idealised tetrahedral OH refined as rotating group:
 O5(H5)
;
_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 7.675
_oxdiff_exptl_absorpt_empirical_full_min 0.354
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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
O2 O 0.38819(16) 0.47536(14) 0.27507(9) 0.0430(4) Uani 1 1 d . . . . .
O4 O 0.80341(18) 0.66847(17) 0.47398(13) 0.0635(5) Uani 1 1 d . . . . .
O1 O 0.3637(2) 0.62600(16) 0.20009(11) 0.0611(5) Uani 1 1 d . . . . .
O5 O 0.00018(19) 0.35004(19) 0.05144(13) 0.0673(5) Uani 1 1 d . . . . .
H5 H -0.071136 0.367047 0.038590 0.101 Uiso 1 1 calc R U . . .
O6 O 0.2049(2) 0.5605(2) 0.01061(13) 0.0823(7) Uani 1 1 d G . . . .
H6A H 0.250974 0.587419 0.068085 0.123 Uiso 1 1 d G U . . .
H6B H 0.149586 0.487543 0.010045 0.123 Uiso 1 1 d G U . . .
O3 O 0.7126(2) 0.7321(2) 0.34367(15) 0.0926(8) Uani 1 1 d . . . . .
C1' C 0.2570(2) 0.3215(2) 0.14075(14) 0.0385(5) Uani 1 1 d . . . . .
C2' C 0.3814(2) 0.4182(2) 0.19068(14) 0.0396(5) Uani 1 1 d . . . . .
C13 C 0.3896(2) 0.5867(2) 0.27193(15) 0.0413(5) Uani 1 1 d . . . . .
C8A' C 0.2578(2) 0.2665(2) 0.05628(15) 0.0409(5) Uani 1 1 d . . . . .
C11 C 0.4274(2) 0.6529(2) 0.36855(14) 0.0393(5) Uani 1 1 d . . . . .
C1" C 0.1232(2) 0.2701(2) 0.17115(15) 0.0404(5) Uani 1 1 d . . . . .
C10 C 0.2901(2) 0.5944(2) 0.40497(14) 0.0399(5) Uani 1 1 d . . . . .
H10 H 0.272239 0.512059 0.416983 0.048 Uiso 1 1 calc R U . . .
C4A' C 0.3848(2) 0.3135(2) 0.02767(15) 0.0440(6) Uani 1 1 d . . . . .
C14 C 0.5590(2) 0.6401(2) 0.43694(15) 0.0427(6) Uani 1 1 d . . . . .
H14A H 0.578724 0.681587 0.497779 0.051 Uiso 1 1 calc R U . . .
H14B H 0.532136 0.555731 0.442611 0.051 Uiso 1 1 calc R U . . .
C4A C 0.1604(2) 0.6004(2) 0.33195(15) 0.0434(6) Uani 1 1 d . . . . .
C3' C 0.5095(2) 0.4640(2) 0.16425(16) 0.0464(6) Uani 1 1 d . . . . .
H3' H 0.592533 0.528995 0.201046 0.056 Uiso 1 1 calc R U . . .
C8A" C 0.1208(2) 0.1987(2) 0.24453(15) 0.0448(6) Uani 1 1 d . . . . .
C10A C 0.3194(2) 0.6760(2) 0.49203(15) 0.0418(6) Uani 1 1 d . . . . .
C8A C 0.3352(2) 0.7920(2) 0.47560(16) 0.0449(6) Uani 1 1 d . . . . .
C9A C 0.1813(3) 0.7167(2) 0.31461(16) 0.0478(6) Uani 1 1 d . . . . .
C2" C -0.0023(3) 0.2834(2) 0.12288(16) 0.0488(6) Uani 1 1 d . . . . .
C15 C 0.6985(3) 0.6873(2) 0.41153(18) 0.0507(6) Uani 1 1 d . . . . .
C8' C 0.1351(3) 0.1662(2) -0.00089(16) 0.0505(6) Uani 1 1 d . . . . .
H8' H 0.051333 0.132658 0.017222 0.061 Uiso 1 1 calc R U . . .
C9 C 0.3271(3) 0.8115(2) 0.37609(16) 0.0481(6) Uani 1 1 d . . . . .
H9 H 0.336820 0.892820 0.365639 0.058 Uiso 1 1 calc R U . . .
C8" C 0.2432(3) 0.1780(2) 0.29550(16) 0.0521(6) Uani 1 1 d . . . . .
H8" H 0.330872 0.214013 0.281912 0.063 Uiso 1 1 calc R U . . .
C4' C 0.5104(3) 0.4124(2) 0.08479(16) 0.0494(6) Uani 1 1 d . . . . .
H4' H 0.595099 0.442347 0.067304 0.059 Uiso 1 1 calc R U . . .
C5 C 0.3278(3) 0.6460(2) 0.58058(16) 0.0530(6) Uani 1 1 d . . . . .
H5A H 0.316899 0.568943 0.592258 0.064 Uiso 1 1 calc R U . . .
C4 C 0.0310(3) 0.5041(2) 0.28480(16) 0.0529(6) Uani 1 1 d . . . . .
H4 H 0.017166 0.426679 0.296976 0.063 Uiso 1 1 calc R U . . .
C12 C 0.4536(3) 0.7859(2) 0.35946(16) 0.0477(6) Uani 1 1 d . . . . .
H12A H 0.546429 0.838703 0.404771 0.057 Uiso 1 1 calc R U . . .
H12B H 0.459056 0.802049 0.297644 0.057 Uiso 1 1 calc R U . . .
C8 C 0.3606(3) 0.8763(2) 0.54729(18) 0.0562(7) Uani 1 1 d . . . . .
H8 H 0.371333 0.953440 0.536039 0.067 Uiso 1 1 calc R U . . .
C4A" C -0.0131(3) 0.1414(2) 0.26669(17) 0.0533(6) Uani 1 1 d . . . . .
C6" C 0.1372(3) 0.1178(2) -0.08194(17) 0.0574(7) Uani 1 1 d . . . . .
H6" H 0.055225 0.051635 -0.118293 0.069 Uiso 1 1 calc R U . . .
C5' C 0.3821(3) 0.2610(2) -0.05753(17) 0.0566(7) Uani 1 1 d . . . . .
H5' H 0.464931 0.292096 -0.076895 0.068 Uiso 1 1 calc R U . . .
C3" C -0.1343(3) 0.2256(3) 0.14454(19) 0.0586(7) Uani 1 1 d . . . . .
H3" H -0.218624 0.234641 0.110981 0.070 Uiso 1 1 calc R U . . .
C4" C -0.1378(3) 0.1571(3) 0.2141(2) 0.0619(7) Uani 1 1 d . . . . .
H4" H -0.225440 0.119433 0.227384 0.074 Uiso 1 1 calc R U . . .
C1 C 0.0710(3) 0.7353(3) 0.24839(18) 0.0618(7) Uani 1 1 d . . . . .
H1 H 0.083868 0.812529 0.236248 0.074 Uiso 1 1 calc R U . . .
C6' C 0.2616(3) 0.1667(3) -0.11102(18) 0.0615(7) Uani 1 1 d . . . . .
H6' H 0.261207 0.134300 -0.167237 0.074 Uiso 1 1 calc R U . . .
C6 C 0.3524(3) 0.7315(3) 0.65194(18) 0.0647(8) Uani 1 1 d . . . . .
H6 H 0.357255 0.711472 0.711578 0.078 Uiso 1 1 calc R U . . .
C2 C -0.0574(3) 0.6387(3) 0.2009(2) 0.0706(8) Uani 1 1 d . . . . .
H2 H -0.130844 0.650940 0.155983 0.085 Uiso 1 1 calc R U . . .
C7 C 0.3700(3) 0.8464(3) 0.63517(19) 0.0649(8) Uani 1 1 d . . . . .
H7 H 0.388186 0.903603 0.683741 0.078 Uiso 1 1 calc R U . . .
C3 C -0.0784(3) 0.5239(3) 0.21905(19) 0.0672(8) Uani 1 1 d . . . . .
H3 H -0.166254 0.459469 0.187044 0.081 Uiso 1 1 calc R U . . .
C7" C 0.2376(4) 0.1072(3) 0.36376(19) 0.0678(8) Uani 1 1 d . . . . .
H7" H 0.320420 0.095243 0.395973 0.081 Uiso 1 1 calc R U . . .
C19 C -0.0152(4) 0.0682(3) 0.3382(2) 0.0747(9) Uani 1 1 d . . . . .
H19 H -0.101596 0.030427 0.352884 0.090 Uiso 1 1 calc R U . . .
C20 C 0.1069(4) 0.0521(3) 0.3859(2) 0.0792(9) Uani 1 1 d . . . . .
H20 H 0.103657 0.004353 0.433327 0.095 Uiso 1 1 calc R U . . .
C16 C 0.9443(3) 0.7052(3) 0.4585(2) 0.0869(10) Uani 1 1 d . . . . .
H16A H 0.930753 0.667773 0.398202 0.130 Uiso 1 1 calc R U . . .
H16B H 1.007871 0.681318 0.505802 0.130 Uiso 1 1 calc R U . . .
H16C H 0.987878 0.790844 0.461160 0.130 Uiso 1 1 calc R U . . .
O7 O -0.5316(9) 0.0753(9) 0.1096(5) 0.309(4) Uani 1 1 d . . . . .
C18 C -0.6826(9) -0.0344(11) 0.1195(7) 0.235(4) Uani 1 1 d . . . . .
H18 H -0.774495 -0.049612 0.125075 0.282 Uiso 1 1 calc R U . . .
C17 C -0.595(2) -0.0866(11) 0.1148(7) 0.342(8) Uani 1 1 d . . . . .
H17 H -0.577698 -0.155622 0.114466 0.411 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'
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
C13 O2 C2' 115.29(17) . . ?
C15 O4 C16 117.7(2) . . ?
C2" O5 H5 109.5 . . ?
H6A O6 H6B 104.5 . . ?
C2' C1' C8A' 117.61(19) . . ?
C2' C1' C1" 123.01(19) . . ?
C8A' C1' C1" 119.37(19) . . ?
C1' C2' O2 120.35(19) . . ?
C1' C2' C3' 123.2(2) . . ?
C3' C2' O2 116.43(19) . . ?
O2 C13 C11 112.53(18) . . ?
O1 C13 O2 122.2(2) . . ?
O1 C13 C11 125.2(2) . . ?
C4A' C8A' C1' 119.8(2) . . ?
C8' C8A' C1' 122.4(2) . . ?
C8' C8A' C4A' 117.8(2) . . ?
C13 C11 C10 108.43(17) . . ?
C13 C11 C14 110.48(18) . . ?
C13 C11 C12 108.53(18) . . ?
C14 C11 C10 108.41(16) . . ?
C14 C11 C12 112.99(18) . . ?
C12 C11 C10 107.87(17) . . ?
C8A" C1" C1' 120.27(19) . . ?
C2" C1" C1' 119.9(2) . . ?
C2" C1" C8A" 119.7(2) . . ?
C11 C10 H10 112.1 . . ?
C4A C10 C11 106.64(17) . . ?
C4A C10 H10 112.1 . . ?
C4A C10 C10A 106.57(17) . . ?
C10A C10 C11 107.09(17) . . ?
C10A C10 H10 112.1 . . ?
C8A' C4A' C4' 119.0(2) . . ?
C8A' C4A' C5' 119.1(2) . . ?
C4' C4A' C5' 121.9(2) . . ?
C11 C14 H14A 108.4 . . ?
C11 C14 H14B 108.4 . . ?
H14A C14 H14B 107.4 . . ?
C15 C14 C11 115.71(19) . . ?
C15 C14 H14A 108.4 . . ?
C15 C14 H14B 108.4 . . ?
C9A C4A C10 113.40(19) . . ?
C4 C4A C10 125.9(2) . . ?
C4 C4A C9A 120.7(2) . . ?
C2' C3' H3' 120.4 . . ?
C4' C3' C2' 119.3(2) . . ?
C4' C3' H3' 120.4 . . ?
C1" C8A" C4A" 119.2(2) . . ?
C8" C8A" C1" 123.1(2) . . ?
C8" C8A" C4A" 117.7(2) . . ?
C8A C10A C10 113.33(19) . . ?
C5 C10A C10 127.1(2) . . ?
C5 C10A C8A 119.5(2) . . ?
C10A C8A C9 113.08(19) . . ?
C8 C8A C10A 120.4(2) . . ?
C8 C8A C9 126.5(2) . . ?
C4A C9A C9 113.28(19) . . ?
C1 C9A C4A 119.5(2) . . ?
C1 C9A C9 127.2(2) . . ?
O5 C2" C1" 119.2(2) . . ?
O5 C2" C3" 120.0(2) . . ?
C1" C2" C3" 120.8(2) . . ?
O4 C15 C14 110.5(2) . . ?
O3 C15 O4 124.2(2) . . ?
O3 C15 C14 125.3(2) . . ?
C8A' C8' H8' 119.4 . . ?
C6" C8' C8A' 121.3(2) . . ?
C6" C8' H8' 119.4 . . ?
C8A C9 C9A 106.62(19) . . ?
C8A C9 H9 111.9 . . ?
C8A C9 C12 105.15(18) . . ?
C9A C9 H9 111.9 . . ?
C9A C9 C12 108.94(19) . . ?
C12 C9 H9 111.9 . . ?
C8A" C8" H8" 118.9 . . ?
C7" C8" C8A" 122.1(2) . . ?
C7" C8" H8" 118.9 . . ?
C4A' C4' H4' 119.4 . . ?
C3' C4' C4A' 121.2(2) . . ?
C3' C4' H4' 119.4 . . ?
C10A C5 H5A 120.3 . . ?
C10A C5 C6 119.5(3) . . ?
C6 C5 H5A 120.3 . . ?
C4A C4 H4 120.4 . . ?
C4A C4 C3 119.2(3) . . ?
C3 C4 H4 120.4 . . ?
C11 C12 H12A 109.6 . . ?
C11 C12 H12B 109.6 . . ?
C9 C12 C11 110.38(18) . . ?
C9 C12 H12A 109.6 . . ?
C9 C12 H12B 109.6 . . ?
H12A C12 H12B 108.1 . . ?
C8A C8 H8 120.0 . . ?
C7 C8 C8A 119.9(3) . . ?
C7 C8 H8 120.0 . . ?
C4" C4A" C8A" 118.4(2) . . ?
C4" C4A" C19 122.8(3) . . ?
C19 C4A" C8A" 118.7(3) . . ?
C8' C6" H6" 119.7 . . ?
C8' C6" C6' 120.6(2) . . ?
C6' C6" H6" 119.7 . . ?
C4A' C5' H5' 119.4 . . ?
C6' C5' C4A' 121.2(2) . . ?
C6' C5' H5' 119.4 . . ?
C2" C3" H3" 120.0 . . ?
C4" C3" C2" 120.0(2) . . ?
C4" C3" H3" 120.0 . . ?
C4A" C4" H4" 119.1 . . ?
C3" C4" C4A" 121.9(2) . . ?
C3" C4" H4" 119.1 . . ?
C9A C1 H1 120.2 . . ?
C2 C1 C9A 119.6(3) . . ?
C2 C1 H1 120.2 . . ?
C6" C6' H6' 120.0 . . ?
C5' C6' C6" 120.0(2) . . ?
C5' C6' H6' 120.0 . . ?
C5 C6 H6 119.7 . . ?
C7 C6 C5 120.5(2) . . ?
C7 C6 H6 119.7 . . ?
C1 C2 H2 119.6 . . ?
C1 C2 C3 120.7(2) . . ?
C3 C2 H2 119.6 . . ?
C8 C7 C6 120.2(2) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C4 C3 H3 119.9 . . ?
C2 C3 C4 120.3(3) . . ?
C2 C3 H3 119.9 . . ?
C8" C7" H7" 119.9 . . ?
C8" C7" C20 120.1(3) . . ?
C20 C7" H7" 119.9 . . ?
C4A" C19 H19 119.4 . . ?
C20 C19 C4A" 121.2(3) . . ?
C20 C19 H19 119.4 . . ?
C7" C20 H20 120.0 . . ?
C19 C20 C7" 120.1(3) . . ?
C19 C20 H20 120.0 . . ?
O4 C16 H16A 109.5 . . ?
O4 C16 H16B 109.5 . . ?
O4 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 O7 C17 43.8(5) . . ?
O7 C18 H18 142.6 . . ?
C17 C18 O7 74.9(9) . . ?
C17 C18 H18 142.6 . . ?
O7 C17 H17 149.3 . . ?
C18 C17 O7 61.3(6) . . ?
C18 C17 H17 149.3 . . ?
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
O2 C2' 1.415(2) . ?
O2 C13 1.358(3) . ?
O4 C15 1.323(3) . ?
O4 C16 1.448(3) . ?
O1 C13 1.196(2) . ?
O5 H5 0.8200 . ?
O5 C2" 1.362(3) . ?
O6 H6A 0.8502 . ?
O6 H6B 0.8501 . ?
O3 C15 1.188(3) . ?
C1' C2' 1.365(3) . ?
C1' C8A' 1.437(3) . ?
C1' C1" 1.496(3) . ?
C2' C3' 1.407(3) . ?
C13 C11 1.525(3) . ?
C8A' C4A' 1.416(3) . ?
C8A' C8' 1.413(3) . ?
C11 C10 1.588(3) . ?
C11 C14 1.528(3) . ?
C11 C12 1.556(3) . ?
C1" C8A" 1.421(3) . ?
C1" C2" 1.377(3) . ?
C10 H10 0.9800 . ?
C10 C4A 1.509(3) . ?
C10 C10A 1.520(3) . ?
C4A' C4' 1.417(3) . ?
C4A' C5' 1.418(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.504(3) . ?
C4A C9A 1.392(3) . ?
C4A C4 1.378(3) . ?
C3' H3' 0.9300 . ?
C3' C4' 1.352(3) . ?
C8A" C8" 1.407(3) . ?
C8A" C4A" 1.435(3) . ?
C10A C8A 1.397(3) . ?
C10A C5 1.380(3) . ?
C8A C9 1.509(3) . ?
C8A C8 1.377(3) . ?
C9A C9 1.516(3) . ?
C9A C1 1.389(3) . ?
C2" C3" 1.414(3) . ?
C8' H8' 0.9300 . ?
C8' C6" 1.361(3) . ?
C9 H9 0.9800 . ?
C9 C12 1.551(3) . ?
C8" H8" 0.9300 . ?
C8" C7" 1.355(4) . ?
C4' H4' 0.9300 . ?
C5 H5A 0.9300 . ?
C5 C6 1.386(4) . ?
C4 H4 0.9300 . ?
C4 C3 1.385(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C8 H8 0.9300 . ?
C8 C7 1.369(4) . ?
C4A" C4" 1.403(4) . ?
C4A" C19 1.412(4) . ?
C6" H6" 0.9300 . ?
C6" C6' 1.399(4) . ?
C5' H5' 0.9300 . ?
C5' C6' 1.349(3) . ?
C3" H3" 0.9300 . ?
C3" C4" 1.353(4) . ?
C4" H4" 0.9300 . ?
C1 H1 0.9300 . ?
C1 C2 1.375(4) . ?
C6' H6' 0.9300 . ?
C6 H6 0.9300 . ?
C6 C7 1.381(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.378(4) . ?
C7 H7 0.9300 . ?
C3 H3 0.9300 . ?
C7" H7" 0.9300 . ?
C7" C20 1.403(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.362(4) . ?
C20 H20 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
O7 C18 1.669(11) . ?
O7 C17 1.837(15) . ?
C18 H18 0.9300 . ?
C18 C17 1.318(12) . ?
C17 H17 0.9300 . ?
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
O2 C2' C3' C4' 179.3(2) . . . . ?
O2 C13 C11 C10 -73.1(2) . . . . ?
O2 C13 C11 C14 45.6(2) . . . . ?
O2 C13 C11 C12 170.02(17) . . . . ?
O1 C13 C11 C10 107.0(2) . . . . ?
O1 C13 C11 C14 -134.3(2) . . . . ?
O1 C13 C11 C12 -9.9(3) . . . . ?
O5 C2" C3" C4" 178.5(2) . . . . ?
C1' C2' C3' C4' 1.4(4) . . . . ?
C1' C8A' C4A' C4' 1.8(3) . . . . ?
C1' C8A' C4A' C5' -177.7(2) . . . . ?
C1' C8A' C8' C6" 178.1(2) . . . . ?
C1' C1" C8A" C8" 3.6(3) . . . . ?
C1' C1" C8A" C4A" -174.4(2) . . . . ?
C1' C1" C2" O5 -4.1(3) . . . . ?
C1' C1" C2" C3" 173.7(2) . . . . ?
C2' O2 C13 O1 11.3(3) . . . . ?
C2' O2 C13 C11 -168.63(16) . . . . ?
C2' C1' C8A' C4A' -0.3(3) . . . . ?
C2' C1' C8A' C8' -179.9(2) . . . . ?
C2' C1' C1" C8A" -75.8(3) . . . . ?
C2' C1' C1" C2" 109.6(3) . . . . ?
C2' C3' C4' C4A' 0.2(4) . . . . ?
C13 O2 C2' C1' -110.1(2) . . . . ?
C13 O2 C2' C3' 71.9(2) . . . . ?
C13 C11 C10 C4A -55.8(2) . . . . ?
C13 C11 C10 C10A -169.57(17) . . . . ?
C13 C11 C14 C15 59.3(3) . . . . ?
C13 C11 C12 C9 109.9(2) . . . . ?
C8A' C1' C2' O2 -179.16(18) . . . . ?
C8A' C1' C2' C3' -1.3(3) . . . . ?
C8A' C1' C1" C8A" 102.9(2) . . . . ?
C8A' C1' C1" C2" -71.7(3) . . . . ?
C8A' C4A' C4' C3' -1.7(4) . . . . ?
C8A' C4A' C5' C6' -0.6(4) . . . . ?
C8A' C8' C6" C6' -0.2(4) . . . . ?
C11 C10 C4A C9A -58.2(2) . . . . ?
C11 C10 C4A C4 122.0(2) . . . . ?
C11 C10 C10A C8A 60.9(2) . . . . ?
C11 C10 C10A C5 -120.8(2) . . . . ?
C11 C14 C15 O4 -178.21(19) . . . . ?
C11 C14 C15 O3 -0.3(4) . . . . ?
C1" C1' C2' O2 -0.5(3) . . . . ?
C1" C1' C2' C3' 177.4(2) . . . . ?
C1" C1' C8A' C4A' -179.07(19) . . . . ?
C1" C1' C8A' C8' 1.4(3) . . . . ?
C1" C8A" C8" C7" -178.4(2) . . . . ?
C1" C8A" C4A" C4" 0.6(3) . . . . ?
C1" C8A" C4A" C19 178.4(2) . . . . ?
C1" C2" C3" C4" 0.7(4) . . . . ?
C10 C11 C14 C15 178.04(18) . . . . ?
C10 C11 C12 C9 -7.4(2) . . . . ?
C10 C4A C9A C9 -2.6(3) . . . . ?
C10 C4A C9A C1 179.5(2) . . . . ?
C10 C4A C4 C3 -179.7(2) . . . . ?
C10 C10A C8A C9 -2.9(3) . . . . ?
C10 C10A C8A C8 179.25(19) . . . . ?
C10 C10A C5 C6 -178.6(2) . . . . ?
C4A' C8A' C8' C6" -1.5(3) . . . . ?
C4A' C5' C6' C6" -1.1(4) . . . . ?
C14 C11 C10 C4A -175.77(17) . . . . ?
C14 C11 C10 C10A 70.5(2) . . . . ?
C14 C11 C12 C9 -127.17(19) . . . . ?
C4A C10 C10A C8A -52.9(2) . . . . ?
C4A C10 C10A C5 125.4(2) . . . . ?
C4A C9A C9 C8A -53.5(2) . . . . ?
C4A C9A C9 C12 59.5(2) . . . . ?
C4A C9A C1 C2 0.0(4) . . . . ?
C4A C4 C3 C2 0.3(4) . . . . ?
C8A" C1" C2" O5 -178.7(2) . . . . ?
C8A" C1" C2" C3" -0.9(3) . . . . ?
C8A" C8" C7" C20 -0.2(4) . . . . ?
C8A" C4A" C4" C3" -0.9(4) . . . . ?
C8A" C4A" C19 C20 0.3(4) . . . . ?
C10A C10 C4A C9A 56.0(2) . . . . ?
C10A C10 C4A C4 -123.9(2) . . . . ?
C10A C8A C9 C9A 56.4(2) . . . . ?
C10A C8A C9 C12 -59.1(2) . . . . ?
C10A C8A C8 C7 -0.2(3) . . . . ?
C10A C5 C6 C7 -0.6(4) . . . . ?
C8A C10A C5 C6 -0.4(3) . . . . ?
C8A C9 C12 C11 63.0(2) . . . . ?
C8A C8 C7 C6 -0.7(4) . . . . ?
C9A C4A C4 C3 0.5(3) . . . . ?
C9A C9 C12 C11 -51.0(2) . . . . ?
C9A C1 C2 C3 0.8(4) . . . . ?
C2" C1" C8A" C8" 178.3(2) . . . . ?
C2" C1" C8A" C4A" 0.2(3) . . . . ?
C2" C3" C4" C4A" 0.2(4) . . . . ?
C8' C8A' C4A' C4' -178.6(2) . . . . ?
C8' C8A' C4A' C5' 1.9(3) . . . . ?
C8' C6" C6' C5' 1.5(4) . . . . ?
C9 C8A C8 C7 -177.7(2) . . . . ?
C9 C9A C1 C2 -177.6(3) . . . . ?
C8" C8A" C4A" C4" -177.5(2) . . . . ?
C8" C8A" C4A" C19 0.3(3) . . . . ?
C8" C7" C20 C19 0.8(4) . . . . ?
C4' C4A' C5' C6' 179.9(2) . . . . ?
C5 C10A C8A C9 178.6(2) . . . . ?
C5 C10A C8A C8 0.8(3) . . . . ?
C5 C6 C7 C8 1.1(4) . . . . ?
C4 C4A C9A C9 177.3(2) . . . . ?
C4 C4A C9A C1 -0.6(3) . . . . ?
C12 C11 C10 C4A 61.6(2) . . . . ?
C12 C11 C10 C10A -52.2(2) . . . . ?
C12 C11 C14 C15 -62.5(2) . . . . ?
C8 C8A C9 C9A -125.9(2) . . . . ?
C8 C8A C9 C12 118.5(2) . . . . ?
C4A" C8A" C8" C7" -0.3(4) . . . . ?
C4A" C19 C20 C7" -0.8(5) . . . . ?
C5' C4A' C4' C3' 177.7(2) . . . . ?
C4" C4A" C19 C20 178.0(3) . . . . ?
C1 C9A C9 C8A 124.2(3) . . . . ?
C1 C9A C9 C12 -122.8(3) . . . . ?
C1 C2 C3 C4 -0.9(4) . . . . ?
C19 C4A" C4" C3" -178.6(3) . . . . ?
C16 O4 C15 O3 0.1(4) . . . . ?
C16 O4 C15 C14 178.1(2) . . . . ?
