#------------------------------------------------------------------------------
#$Date: 2024-02-05 07:11:06 +0200 (Mon, 05 Feb 2024) $
#$Revision: 289673 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/09/1570919.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_1570919
loop_
_publ_author_name
'Kamma, Koteswara Rao'
'Cho, Joungmo'
'Won, Hyo Jun'
'Nam, So-Yeon'
'Le, Ngan Hong'
'Jung, Je Hyeong'
'Lee, Kee-In'
_publ_section_title
;
 Synthetic Studies toward 5,6,7,3',4'-Monomethoxytetrahydroxyflavones:
 Synthesis of Pedalitin.
;
_journal_issue                   2
_journal_name_full               'Molecules (Basel, Switzerland)'
_journal_page_first              513
_journal_paper_doi               10.3390/molecules29020513
_journal_volume                  29
_journal_year                    2024
_chemical_formula_moiety         'C24 H20 O11'
_chemical_formula_sum            'C24 H20 O11'
_chemical_formula_weight         484.40
_chemical_name_systematic        Ac-B
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-05-02
_audit_creation_method
;
Olex2 1.5-ac5-018
(compiled 2021.09.08 svn.r13c46975 for Rigaku Oxford Diffraction, GUI svn.r6396)
;
_cell_angle_alpha                108.253(2)
_cell_angle_beta                 93.6270(10)
_cell_angle_gamma                112.862(2)
_cell_formula_units_Z            2
_cell_length_a                   8.94440(10)
_cell_length_b                   10.9710(2)
_cell_length_c                   13.8699(2)
_cell_measurement_reflns_used    18289
_cell_measurement_temperature    298
_cell_measurement_theta_max      75.8490
_cell_measurement_theta_min      3.4020
_cell_volume                     1164.11(4)
_computing_cell_refinement       'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5-ac5-018 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-018 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      298
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.932
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω   -119.00 -94.00   0.50    0.47    --  -48.42-130.00-127.00   50
  2  ω    -89.00 -57.00   0.50    0.47    --  -48.42 130.00 -55.00   64
  3  ω    -95.00 -69.00   0.50    0.47    --  -48.42-141.00  59.00   52
  4  ω     80.00 105.00   0.50    0.47    --   48.42-141.00  59.00   50
  5  ω     47.00  74.00   0.50    0.47    --   48.42-141.00  59.00   54
  6  ω     47.00  73.00   0.50    0.47    --   48.42-130.00-127.00   52
  7  ω   -151.00 -79.00   0.50    1.87    --  -91.75-130.00-127.00  144
  8  ω   -147.00-107.00   0.50    1.87    --  -91.75-141.00  59.00   80
  9  ω     68.00 114.00   0.50    1.87    --  106.52-130.00-127.00   92
 10  ω     74.00 124.00   0.50    1.87    --  106.52-141.00  59.00  100
 11  ω     37.00  63.00   0.50    1.87    --  106.52-130.00-127.00   52
 12  ω    111.00 136.00   0.50    1.87    --  106.52 130.00 -55.00   50
 13  ω    115.00 141.00   0.50    1.87    --  106.52 141.00 117.00   52
 14  ω    -60.00 -35.00   0.50    0.47    --   14.00 168.00-178.32   50
 15  ω    -11.00  19.00   0.50    0.47    --   22.00  99.00 152.31   60
 16  ω     -5.00  34.00   0.50    0.47    --   22.00  91.00 -60.04   78
 17  ω      3.00  28.00   0.50    0.47    --   34.00  94.00 -21.59   50
 18  ω     14.00  40.00   0.50    0.47    --   42.00  91.00  11.61   52
 19  ω     17.00  42.00   0.50    0.47    --   46.00  90.00-105.40   50
 20  ω     17.00  42.00   0.50    0.47    --   46.00  90.00  32.16   50
 21  ω     17.00  42.00   0.50    0.47    --   46.00  90.00-138.43   50
 22  ω    -66.00 -36.00   0.50    0.47    --  -48.42 -19.00-120.00   60
 23  ω    -87.00 -35.00   0.50    0.47    --  -48.42 -38.00 120.00  104
 24  ω    -52.00 -26.00   0.50    0.47    --  -48.42 -77.00 -90.00   52
 25  ω    -52.00 -18.00   0.50    0.47    --  -48.42 130.00 -55.00   68
 26  ω    -78.00 -26.00   0.50    0.47    --  -48.42 -77.00  60.00  104
 27  ω    -46.00 -21.00   0.50    0.47    --  -48.42 141.00 117.00   50
 28  ω    -53.00 -27.00   0.50    0.47    --  -48.42 -77.00 120.00   52
 29  ω    -98.00 -51.00   0.50    0.47    --  -48.42 141.00 117.00   94
 30  ω    -57.00 -28.00   0.50    0.47    --  -50.00 -75.00  10.20   58
 31  ω   -122.00 -97.00   0.50    0.47    --  -50.00 -75.00  10.20   50
 32  ω     77.00 103.00   0.50    0.47    --   54.00  76.00-165.15   52
 33  ω     33.00  68.00   0.50    0.47    --   54.00  74.00-106.97   70
 34  ω     32.00  58.00   0.50    0.47    --   54.00  75.00 100.65   52
 35  ω     33.00  59.00   0.50    0.47    --   54.00  77.00 160.36   52
 36  ω     32.00  58.00   0.50    0.47    --   54.00  76.00-165.15   52
 37  ω     37.00  62.00   0.50    0.47    --   58.00  72.00 133.74   50
 38  ω    -81.00 -40.00   0.50    0.47    --  -62.00 -75.00 108.03   82
 39  ω    -72.00 -46.00   0.50    0.47    --  -62.00 -66.00 166.69   52
 40  ω    -64.00 -39.00   0.50    0.47    --  -62.00 -77.00  30.87   50
 41  ω     40.00  67.00   0.50    0.47    --   62.00  77.00 -42.44   54
 42  ω    -97.00 -46.00   0.50    0.47    --  -66.00 -70.00-100.71  102
 43  ω    -84.00 -46.00   0.50    0.47    --  -66.00 -70.00 -26.09   76
 44  ω   -135.00-109.00   0.50    0.47    --  -66.00 -72.00-137.74   52
 45  ω    -72.00 -46.00   0.50    0.47    --  -66.00 -72.00-137.74   52
 46  ω   -135.00-108.00   0.50    0.47    --  -66.00 -72.00  -8.67   54
 47  ω    -79.00 -45.00   0.50    0.47    --  -66.00 -72.00  -8.67   68
 48  ω    -74.00 -48.00   0.50    0.47    --  -70.00 -75.00-147.47   52
 49  ω    -77.00 -51.00   0.50    0.47    --  -70.00 -67.00 -58.33   52
 50  ω    -80.00 -54.00   0.50    0.47    --  -70.00 -61.00-138.42   52
 51  ω    -82.00 -56.00   0.50    0.47    --  -70.00 -62.00  54.76   52
 52  ω    -76.00 -51.00   0.50    1.87    --  -74.00 -76.00 174.80   50
 53  ω    -77.00 -51.00   0.50    1.87    --  -74.00 -76.00  93.85   52
 54  ω    -77.00 -51.00   0.50    1.87    --  -74.00 -76.00-173.43   52
 55  ω    -76.00 -51.00   0.50    1.87    --  -74.00 -77.00 150.51   50
 56  ω    -89.00 -56.00   0.50    1.87    --  -74.00 -73.00  42.36   66
 57  ω    -79.00 -53.00   0.50    1.87    --  -74.00 -74.00  58.07   52
 58  ω    -82.00 -56.00   0.50    1.87    --  -74.00 -67.00 -35.11   52
 59  ω    -83.00 -57.00   0.50    1.87    --  -78.00 -76.00  14.60   52
 60  ω    -90.00 -62.00   0.50    1.87    --  -82.00 -69.00-153.94   56
 61  ω    -91.00 -61.00   0.50    1.87    --  -82.00 -72.00-114.27   60
 62  ω    -88.00 -62.00   0.50    1.87    --  -82.00 -71.00-100.43   52
 63  ω    -90.00 -64.00   0.50    1.87    --  -82.00 -65.00 -82.36   52
 64  ω    -89.00 -64.00   0.50    1.87    --  -82.00 -64.00 -64.71   50
 65  ω    -90.00 -59.00   0.50    1.87    --  -82.00 -76.00-178.47   62
 66  ω    -90.00 -63.00   0.50    1.87    --  -82.00 -68.00-135.90   54
 67  ω    -85.00 -60.00   0.50    1.87    --  -82.00 -75.00  78.11   50
 68  ω   -111.00 -63.00   0.50    1.87    --  -86.00 -77.00 132.46   96
 69  ω   -158.00-120.00   0.50    1.87    --  -86.00 -77.00 132.46   76
 70  ω    -93.00 -63.00   0.50    1.87    --  -86.00 -76.00-161.13   60
 71  ω    -92.00 -64.00   0.50    1.87    --  -86.00 -75.00  66.78   56
 72  ω   -158.00-116.00   0.50    1.87    --  -86.00 -75.00  66.78   84
 73  ω   -126.00 -72.00   0.50    1.87    --  -90.00 -64.00 143.15  108
 74  ω   -160.00 -79.00   0.50    1.87    --  -91.75 -61.00 150.00  162
 75  ω    -98.00 -71.00   0.50    1.87    --  -91.75 -77.00-180.00   54
 76  ω   -142.00-116.00   0.50    1.87    --  -91.75 -77.00-180.00   52
 77  ω   -162.00 -77.00   0.50    1.87    --  -91.75 -65.00 -26.04  170
 78  ω    -70.00 -19.00   0.50    1.87    --  -91.75  61.00 -30.00  102
 79  ω   -104.00 -70.00   0.50    1.87    --  -91.75 -75.00  51.10   68
 80  ω   -152.00-127.00   0.50    1.87    --  -91.75 -74.00  17.11   50
 81  ω   -152.00-126.00   0.50    1.87    --  -91.75 -75.00  51.10   52
 82  ω   -102.00 -71.00   0.50    1.87    --  -91.75 -74.00-107.50   62
 83  ω   -158.00-113.00   0.50    1.87    --  -91.75 -74.00-107.50   90
 84  ω   -100.00 -74.00   0.50    1.87    --  -91.75 -72.00 -75.90   52
 85  ω   -125.00 -74.00   0.50    1.87    --  -91.75 -68.00  28.42  102
 86  ω    -95.00 -69.00   0.50    1.87    --  -91.75 -77.00   0.00   52
 87  ω   -159.00-133.00   0.50    1.87    --  -91.75 -77.00   0.00   52
 88  ω   -163.00 -75.00   0.50    1.87    --  -91.75 -66.00   2.10  176
 89  ω    -97.00 -72.00   0.50    1.87    --  -91.75 -77.00 -90.00   50
 90  ω   -161.00 -73.00   0.50    1.87    --  -91.75 -71.00-163.76  176
 91  ω   -148.00-102.00   0.50    1.87    --  -91.75 -77.00 -90.00   92
 92  ω   -152.00-124.00   0.50    1.87    --  -91.75 -65.00  94.83   56
 93  ω    -46.00 -20.00   0.50    1.87    --  -91.75  45.00 -30.00   52
 94  ω   -126.00 -71.00   0.50    1.87    --  -91.75 -74.00  17.11  110
 95  ω    -98.00 -72.00   0.50    1.87    --  -91.75 -72.00 -28.66   52
 96  ω   -159.00 -75.00   0.50    1.87    --  -91.75 -63.00  83.11  168
 97  ω   -163.00 -70.00   0.50    1.87    --  -91.75 -77.00-125.21  186
 98  ω   -115.00 -76.00   0.50    1.87    --  -91.75 -65.00  94.83   78
 99  ω   -100.00 -71.00   0.50    1.87    --  -91.75 -77.00 -60.00   58
100  ω    -98.00 -71.00   0.50    1.87    --  -91.75 -73.00 -46.10   54
101  ω   -163.00-113.00   0.50    1.87    --  -91.75 -73.00 -46.10  100
102  ω   -154.00-129.00   0.50    1.87    --  -91.75 -67.00 118.08   50
103  ω   -103.00 -77.00   0.50    1.87    --  -91.75 -67.00 118.08   52
104  ω   -161.00-112.00   0.50    1.87    --  -91.75 -77.00 -60.00   98
105  ω    -84.00 -59.00   0.50    1.87    --  -91.75 141.00 117.00   50
106  ω     61.00 112.00   0.50    1.87    --  106.52-126.00   0.00  102
107  ω    106.00 154.00   0.50    1.87    --  106.52 126.00-180.00   96
108  ω     34.00  68.00   0.50    1.87    --  106.52 -61.00-180.00   68
109  ω     43.00 111.00   0.50    1.87    --  106.52-126.00 150.00  136
110  ω     46.00  97.00   0.50    1.87    --  106.52 -95.00 -90.00  102
111  ω     57.00 108.00   0.50    1.87    --  106.52-126.00 -90.00  102
112  ω     34.00  71.00   0.50    1.87    --  106.52 -61.00 120.00   74
113  ω     72.00 108.00   0.50    1.87    --  106.52-113.00  74.39   72
114  ω     51.00  93.00   0.50    1.87    --  106.52 -77.00 120.00   84
115  ω     45.00  70.00   0.50    1.87    --  106.52-113.00  74.39   50
116  ω     37.00  70.00   0.50    1.87    --  106.52 -61.00-150.00   66
117  ω     35.00 104.00   0.50    1.87    --  106.52 -77.00  30.00  138
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1852209000
_diffrn_orient_matrix_UB_12      0.0666710000
_diffrn_orient_matrix_UB_13      -0.0035452000
_diffrn_orient_matrix_UB_21      -0.0453696000
_diffrn_orient_matrix_UB_22      -0.0677726000
_diffrn_orient_matrix_UB_23      -0.1195054000
_diffrn_orient_matrix_UB_31      -0.0144185000
_diffrn_orient_matrix_UB_32      0.1334453000
_diffrn_orient_matrix_UB_33      -0.0049529000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_unetI/netI     0.0198
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.932
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            35274
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.932
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.758
_diffrn_reflns_theta_min         3.433
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.947
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70310
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.121a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light colourless'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.766
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.0024(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     342
_refine_ls_number_reflns         4581
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0630
_refine_ls_R_factor_gt           0.0543
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0937P)²+0.1979P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1661
_refine_ls_wR_factor_ref         0.1754
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3652
_reflns_number_total             4581
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            6_auto.cif
_cod_data_source_block           20230426_auto
_cod_database_code               1570919
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C24H20O11
_chemical_oxdiff_usercomment     Ac-B
_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   0.963
_shelx_estimated_absorpt_t_min   0.703
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(O9B)=1-FVAR(1)
 Sof(O9A)=FVAR(1)
 Sof(O11B)=1-FVAR(2)
 Sof(O11A)=FVAR(2)
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C8(H8), C16(H16), C19(H19), C20(H20)
3.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C22(H22A,H22B,
 H22C), C24(H24A,H24B,H24C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_original_sample_id Ac-B
_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 1.510
_oxdiff_exptl_absorpt_empirical_full_min 0.543
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
O1 O 0.47789(15) 0.71945(15) 0.49213(9) 0.0677(4) Uani 1 1 d . . . . .
O2 O 0.8031(2) 0.6795(2) 0.30578(13) 0.0964(5) Uani 1 1 d . . . . .
O3 O 0.59365(19) 0.38953(18) 0.21757(10) 0.0821(4) Uani 1 1 d . . . . .
O4 O 0.7761(2) 0.4025(2) 0.34150(13) 0.1079(6) Uani 1 1 d . . . . .
O5 O 0.3282(2) 0.17712(16) 0.23214(10) 0.0808(4) Uani 1 1 d . . . . .
O6 O 0.1598(2) 0.17735(17) 0.10756(12) 0.0913(5) Uani 1 1 d . . . . .
O7 O 0.11545(19) 0.22792(16) 0.34874(11) 0.0818(4) Uani 1 1 d . . . . .
O8 O 0.3737(2) 1.0941(2) 0.73318(12) 0.0928(5) Uani 1 1 d . . . . .
O9A O 0.4621(4) 1.1219(4) 0.8936(2) 0.1043(14) Uani 0.669(7) 1 d . . P A 1
O9B O 0.3777(9) 0.9781(9) 0.8236(7) 0.122(3) Uani 0.331(7) 1 d . . P A 2
O10 O 0.6635(3) 1.33742(19) 0.79750(14) 0.1019(6) Uani 1 1 d . . . . .
O11A O 0.8553(5) 1.3557(3) 0.9167(2) 0.1048(13) Uani 0.743(9) 1 d . . P B 1
O11B O 0.699(2) 1.2998(10) 0.9317(6) 0.131(7) Uani 0.257(9) 1 d . . P B 2
C1 C 0.6215(2) 0.8321(2) 0.50194(13) 0.0640(4) Uani 1 1 d . . . . .
C2 C 0.7288(3) 0.8200(2) 0.44044(15) 0.0710(5) Uani 1 1 d . . . . .
H2 H 0.824614 0.900818 0.449066 0.085 Uiso 1 1 calc R U . . .
C3 C 0.7021(3) 0.6868(2) 0.36139(15) 0.0715(5) Uani 1 1 d . . . . .
C4 C 0.5506(2) 0.5662(2) 0.35601(13) 0.0660(5) Uani 1 1 d . . . . .
C5 C 0.5028(3) 0.4246(2) 0.29025(13) 0.0698(5) Uani 1 1 d . . . . .
C6 C 0.3603(3) 0.3160(2) 0.29059(14) 0.0713(5) Uani 1 1 d . . . . .
C7 C 0.2532(2) 0.3431(2) 0.35553(14) 0.0690(5) Uani 1 1 d . . . . .
C8 C 0.2959(2) 0.4809(2) 0.42112(14) 0.0697(5) Uani 1 1 d . . . . .
H8 H 0.226910 0.501525 0.464560 0.084 Uiso 1 1 calc R U . . .
C9 C 0.4429(2) 0.5874(2) 0.42100(13) 0.0630(4) Uani 1 1 d . . . . .
C10 C 0.7338(3) 0.3827(3) 0.25313(17) 0.0823(6) Uani 1 1 d . . . . .
C11 C 0.8208(4) 0.3491(4) 0.1671(2) 0.1161(10) Uani 1 1 d . . . . .
H11A H 0.746204 0.262266 0.112093 0.174 Uiso 1 1 calc R U . . .
H11B H 0.915418 0.338461 0.192737 0.174 Uiso 1 1 calc R U . . .
H11C H 0.856684 0.425122 0.141184 0.174 Uiso 1 1 calc R U . . .
C13 C 0.2104(3) -0.0283(3) 0.0819(2) 0.0957(7) Uani 1 1 d . . . . .
H13A H 0.309933 -0.021660 0.056915 0.144 Uiso 1 1 calc R U . . .
H13B H 0.117128 -0.078316 0.024208 0.144 Uiso 1 1 calc R U . . .
H13C H 0.194856 -0.078679 0.128585 0.144 Uiso 1 1 calc R U . . .
C14 C 0.0028(3) 0.2490(3) 0.4123(2) 0.0859(6) Uani 1 1 d . . . . .
H14A H -0.044464 0.304631 0.392092 0.129 Uiso 1 1 calc R U . . .
H14B H 0.060632 0.298232 0.483659 0.129 Uiso 1 1 calc R U . . .
H14C H -0.084089 0.158568 0.404258 0.129 Uiso 1 1 calc R U . . .
C15 C 0.6381(2) 0.9628(2) 0.58354(14) 0.0649(5) Uani 1 1 d . . . . .
C16 C 0.5030(2) 0.9664(2) 0.62690(14) 0.0688(5) Uani 1 1 d . . . . .
H16 H 0.403704 0.884502 0.606526 0.083 Uiso 1 1 calc R U . . .
C17 C 0.5157(3) 1.0903(2) 0.69964(15) 0.0720(5) Uani 1 1 d . . . . .
C18 C 0.6614(3) 1.2117(3) 0.73047(16) 0.0783(6) Uani 1 1 d . . . . .
C19 C 0.7981(3) 1.2099(3) 0.69055(19) 0.0868(6) Uani 1 1 d . . . . .
H19 H 0.897780 1.291662 0.712647 0.104 Uiso 1 1 calc R U . . .
C20 C 0.7853(3) 1.0849(3) 0.61710(17) 0.0795(6) Uani 1 1 d . . . . .
H20 H 0.877302 1.083261 0.589986 0.095 Uiso 1 1 calc R U . . .
C21 C 0.3480(3) 1.0939(3) 0.8244(2) 0.0933(7) Uani 1 1 d . . . . .
C22 C 0.1961(3) 1.1084(3) 0.8450(2) 0.1009(8) Uani 1 1 d . . . . .
H22A H 0.182244 1.172690 0.815481 0.151 Uiso 1 1 calc R U . . .
H22B H 0.203788 1.145002 0.918595 0.151 Uiso 1 1 calc R U . . .
H22C H 0.102484 1.017099 0.814286 0.151 Uiso 1 1 calc R U . . .
C23 C 0.7505(4) 1.3960(3) 0.8935(2) 0.0974(8) Uani 1 1 d . . . . .
C24 C 0.7337(5) 1.5257(3) 0.9560(3) 0.1226(11) Uani 1 1 d . . . . .
H24A H 0.838745 1.594942 1.000832 0.184 Uiso 1 1 calc R U . . .
H24B H 0.652566 1.501457 0.997215 0.184 Uiso 1 1 calc R U . . .
H24C H 0.699052 1.564350 0.910454 0.184 Uiso 1 1 calc R U . . .
C25 C 0.2248(3) 0.1165(2) 0.13712(15) 0.0699(5) Uani 1 1 d . . . . .
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'
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
C1 O1 C9 119.91(14) . . ?
C10 O3 C5 116.91(15) . . ?
C25 O5 C6 117.03(14) . . ?
C7 O7 C14 118.02(17) . . ?
C21 O8 C17 122.61(18) . . ?
C23 O10 C18 119.57(19) . . ?
O1 C1 C15 111.75(15) . . ?
C2 C1 O1 121.73(18) . . ?
C2 C1 C15 126.49(19) . . ?
C1 C2 H2 118.6 . . ?
C1 C2 C3 122.8(2) . . ?
C3 C2 H2 118.6 . . ?
O2 C3 C2 121.2(2) . . ?
O2 C3 C4 124.6(2) . . ?
C2 C3 C4 114.22(16) . . ?
C5 C4 C3 124.87(17) . . ?
C9 C4 C3 119.73(18) . . ?
C9 C4 C5 115.38(19) . . ?
O3 C5 C4 121.4(2) . . ?
C6 C5 O3 116.71(18) . . ?
C6 C5 C4 121.84(17) . . ?
O5 C6 C7 119.9(2) . . ?
C5 C6 O5 119.23(18) . . ?
C5 C6 C7 120.72(19) . . ?
O7 C7 C6 115.59(18) . . ?
O7 C7 C8 125.32(18) . . ?
C8 C7 C6 119.1(2) . . ?
C7 C8 H8 120.7 . . ?
C9 C8 C7 118.69(17) . . ?
C9 C8 H8 120.7 . . ?
O1 C9 C4 121.47(18) . . ?
O1 C9 C8 114.29(15) . . ?
C8 C9 C4 124.23(18) . . ?
O3 C10 C11 110.7(2) . . ?
O4 C10 O3 122.15(18) . . ?
O4 C10 C11 127.1(2) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C25 C13 H13A 109.5 . . ?
C25 C13 H13B 109.5 . . ?
C25 C13 H13C 109.5 . . ?
O7 C14 H14A 109.5 . . ?
O7 C14 H14B 109.5 . . ?
O7 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C1 120.12(18) . . ?
C20 C15 C1 121.17(16) . . ?
C20 C15 C16 118.69(19) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 C15 120.3(2) . . ?
C17 C16 H16 119.9 . . ?
C16 C17 O8 118.7(2) . . ?
C18 C17 O8 120.54(19) . . ?
C18 C17 C16 120.45(18) . . ?
C17 C18 O10 118.1(2) . . ?
C17 C18 C19 120.4(2) . . ?
C19 C18 O10 121.4(2) . . ?
C18 C19 H19 120.4 . . ?
C18 C19 C20 119.2(2) . . ?
C20 C19 H19 120.4 . . ?
C15 C20 C19 120.99(19) . . ?
C15 C20 H20 119.5 . . ?
C19 C20 H20 119.5 . . ?
O8 C21 O9B 99.4(4) . . ?
O8 C21 C22 112.7(2) . . ?
O9A C21 O8 120.9(2) . . ?
O9A C21 C22 122.9(3) . . ?
O9B C21 C22 124.2(3) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O10 C23 C24 112.9(3) . . ?
O11A C23 O10 119.1(2) . . ?
O11A C23 C24 126.7(3) . . ?
O11B C23 O10 105.5(5) . . ?
O11B C23 C24 111.7(5) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O5 C25 C13 110.69(17) . . ?
O6 C25 O5 121.52(18) . . ?
O6 C25 C13 127.8(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.354(2) . ?
O1 C9 1.372(2) . ?
O2 C3 1.234(2) . ?
O3 C5 1.389(2) . ?
O3 C10 1.355(3) . ?
O4 C10 1.185(3) . ?
O5 C6 1.385(2) . ?
O5 C25 1.361(2) . ?
O6 C25 1.182(2) . ?
O7 C7 1.351(3) . ?
O7 C14 1.419(3) . ?
O8 C17 1.391(2) . ?
O8 C21 1.301(3) . ?
O9A C21 1.227(3) . ?
O9B C21 1.392(7) . ?
O10 C18 1.394(3) . ?
O10 C23 1.317(3) . ?
O11A C23 1.245(4) . ?
O11B C23 1.269(11) . ?
C1 C2 1.341(3) . ?
C1 C15 1.469(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.444(3) . ?
C3 C4 1.458(3) . ?
C4 C5 1.405(3) . ?
C4 C9 1.396(2) . ?
C5 C6 1.367(3) . ?
C6 C7 1.407(3) . ?
C7 C8 1.380(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.379(3) . ?
C10 C11 1.493(3) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C13 C25 1.480(3) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.392(2) . ?
C15 C20 1.381(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.373(3) . ?
C17 C18 1.371(3) . ?
C18 C19 1.378(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.385(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.464(3) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 C24 1.486(4) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 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
O1 C1 C2 C3 -1.5(3) . . . . ?
O1 C1 C15 C16 -11.4(2) . . . . ?
O1 C1 C15 C20 170.16(17) . . . . ?
O2 C3 C4 C5 3.0(3) . . . . ?
O2 C3 C4 C9 -178.33(18) . . . . ?
O3 C5 C6 O5 10.2(2) . . . . ?
O3 C5 C6 C7 -174.75(15) . . . . ?
O5 C6 C7 O7 -5.5(2) . . . . ?
O5 C6 C7 C8 173.41(15) . . . . ?
O7 C7 C8 C9 178.54(16) . . . . ?
O8 C17 C18 O10 1.1(3) . . . . ?
O8 C17 C18 C19 -174.75(19) . . . . ?
O10 C18 C19 C20 -174.3(2) . . . . ?
C1 O1 C9 C4 -1.5(2) . . . . ?
C1 O1 C9 C8 177.82(14) . . . . ?
C1 C2 C3 O2 179.68(19) . . . . ?
C1 C2 C3 C4 -1.5(3) . . . . ?
C1 C15 C16 C17 -176.89(16) . . . . ?
C1 C15 C20 C19 176.91(19) . . . . ?
C2 C1 C15 C16 166.92(18) . . . . ?
C2 C1 C15 C20 -11.6(3) . . . . ?
C2 C3 C4 C5 -175.82(16) . . . . ?
C2 C3 C4 C9 2.9(2) . . . . ?
C3 C4 C5 O3 -4.9(3) . . . . ?
C3 C4 C5 C6 178.70(16) . . . . ?
C3 C4 C9 O1 -1.5(3) . . . . ?
C3 C4 C9 C8 179.23(16) . . . . ?
C4 C5 C6 O5 -173.30(15) . . . . ?
C4 C5 C6 C7 1.8(3) . . . . ?
C5 O3 C10 O4 1.6(4) . . . . ?
C5 O3 C10 C11 -178.0(2) . . . . ?
C5 C4 C9 O1 177.28(14) . . . . ?
C5 C4 C9 C8 -2.0(3) . . . . ?
C5 C6 C7 O7 179.46(16) . . . . ?
C5 C6 C7 C8 -1.6(3) . . . . ?
C6 O5 C25 O6 -3.1(3) . . . . ?
C6 O5 C25 C13 176.8(2) . . . . ?
C6 C7 C8 C9 -0.3(3) . . . . ?
C7 C8 C9 O1 -177.18(15) . . . . ?
C7 C8 C9 C4 2.1(3) . . . . ?
C9 O1 C1 C2 3.0(2) . . . . ?
C9 O1 C1 C15 -178.60(13) . . . . ?
C9 C4 C5 O3 176.35(15) . . . . ?
C9 C4 C5 C6 0.0(3) . . . . ?
C10 O3 C5 C4 79.3(2) . . . . ?
C10 O3 C5 C6 -104.2(2) . . . . ?
C14 O7 C7 C6 -179.87(17) . . . . ?
C14 O7 C7 C8 1.3(3) . . . . ?
C15 C1 C2 C3 -179.59(17) . . . . ?
C15 C16 C17 O8 173.28(16) . . . . ?
C15 C16 C17 C18 -0.1(3) . . . . ?
C16 C15 C20 C19 -1.6(3) . . . . ?
C16 C17 C18 O10 174.41(18) . . . . ?
C16 C17 C18 C19 -1.5(3) . . . . ?
C17 O8 C21 O9A 16.4(5) . . . . ?
C17 O8 C21 O9B -50.6(5) . . . . ?
C17 O8 C21 C22 175.9(2) . . . . ?
C17 C18 C19 C20 1.5(3) . . . . ?
C18 O10 C23 O11A 14.6(4) . . . . ?
C18 O10 C23 O11B -55.3(8) . . . . ?
C18 O10 C23 C24 -177.5(3) . . . . ?
C18 C19 C20 C15 0.1(4) . . . . ?
C20 C15 C16 C17 1.6(3) . . . . ?
C21 O8 C17 C16 106.5(3) . . . . ?
C21 O8 C17 C18 -80.1(3) . . . . ?
C23 O10 C18 C17 112.0(3) . . . . ?
C23 O10 C18 C19 -72.1(3) . . . . ?
C25 O5 C6 C5 -97.9(2) . . . . ?
C25 O5 C6 C7 87.0(2) . . . . ?
