Synthetic Studies toward 5,6,7,3',4'-Monomethoxytetrahydroxyflavones: Synthesis of Pedalitin.
Kamma, Koteswara Rao; Cho, Joungmo; Won, Hyo Jun; Nam, So-Yeon; Le, Ngan Hong; Jung, Je Hyeong; Lee, Kee-In; Molecules (Basel, Switzerland) 29 (2024) 513–; doi:10.3390/molecules29020513

data_1570919
_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  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w   -119.00 -94.00   0.50    0.47    --  -48.42-130.00-127.00   50
  2  \w    -89.00 -57.00   0.50    0.47    --  -48.42 130.00 -55.00   64
  3  \w    -95.00 -69.00   0.50    0.47    --  -48.42-141.00  59.00   52
  4  \w     80.00 105.00   0.50    0.47    --   48.42-141.00  59.00   50
  5  \w     47.00  74.00   0.50    0.47    --   48.42-141.00  59.00   54
  6  \w     47.00  73.00   0.50    0.47    --   48.42-130.00-127.00   52
  7  \w   -151.00 -79.00   0.50    1.87    --  -91.75-130.00-127.00  144
  8  \w   -147.00-107.00   0.50    1.87    --  -91.75-141.00  59.00   80
  9  \w     68.00 114.00   0.50    1.87    --  106.52-130.00-127.00   92
 10  \w     74.00 124.00   0.50    1.87    --  106.52-141.00  59.00  100
 11  \w     37.00  63.00   0.50    1.87    --  106.52-130.00-127.00   52
 12  \w    111.00 136.00   0.50    1.87    --  106.52 130.00 -55.00   50
 13  \w    115.00 141.00   0.50    1.87    --  106.52 141.00 117.00   52
 14  \w    -60.00 -35.00   0.50    0.47    --   14.00 168.00-178.32   50
 15  \w    -11.00  19.00   0.50    0.47    --   22.00  99.00 152.31   60
 16  \w     -5.00  34.00   0.50    0.47    --   22.00  91.00 -60.04   78
 17  \w      3.00  28.00   0.50    0.47    --   34.00  94.00 -21.59   50
 18  \w     14.00  40.00   0.50    0.47    --   42.00  91.00  11.61   52
 19  \w     17.00  42.00   0.50    0.47    --   46.00  90.00-105.40   50
 20  \w     17.00  42.00   0.50    0.47    --   46.00  90.00  32.16   50
 21  \w     17.00  42.00   0.50    0.47    --   46.00  90.00-138.43   50
 22  \w    -66.00 -36.00   0.50    0.47    --  -48.42 -19.00-120.00   60
 23  \w    -87.00 -35.00   0.50    0.47    --  -48.42 -38.00 120.00  104
 24  \w    -52.00 -26.00   0.50    0.47    --  -48.42 -77.00 -90.00   52
 25  \w    -52.00 -18.00   0.50    0.47    --  -48.42 130.00 -55.00   68
 26  \w    -78.00 -26.00   0.50    0.47    --  -48.42 -77.00  60.00  104
 27  \w    -46.00 -21.00   0.50    0.47    --  -48.42 141.00 117.00   50
 28  \w    -53.00 -27.00   0.50    0.47    --  -48.42 -77.00 120.00   52
 29  \w    -98.00 -51.00   0.50    0.47    --  -48.42 141.00 117.00   94
 30  \w    -57.00 -28.00   0.50    0.47    --  -50.00 -75.00  10.20   58
 31  \w   -122.00 -97.00   0.50    0.47    --  -50.00 -75.00  10.20   50
 32  \w     77.00 103.00   0.50    0.47    --   54.00  76.00-165.15   52
 33  \w     33.00  68.00   0.50    0.47    --   54.00  74.00-106.97   70
 34  \w     32.00  58.00   0.50    0.47    --   54.00  75.00 100.65   52
 35  \w     33.00  59.00   0.50    0.47    --   54.00  77.00 160.36   52
 36  \w     32.00  58.00   0.50    0.47    --   54.00  76.00-165.15   52
 37  \w     37.00  62.00   0.50    0.47    --   58.00  72.00 133.74   50
 38  \w    -81.00 -40.00   0.50    0.47    --  -62.00 -75.00 108.03   82
 39  \w    -72.00 -46.00   0.50    0.47    --  -62.00 -66.00 166.69   52
 40  \w    -64.00 -39.00   0.50    0.47    --  -62.00 -77.00  30.87   50
 41  \w     40.00  67.00   0.50    0.47    --   62.00  77.00 -42.44   54
 42  \w    -97.00 -46.00   0.50    0.47    --  -66.00 -70.00-100.71  102
 43  \w    -84.00 -46.00   0.50    0.47    --  -66.00 -70.00 -26.09   76
 44  \w   -135.00-109.00   0.50    0.47    --  -66.00 -72.00-137.74   52
 45  \w    -72.00 -46.00   0.50    0.47    --  -66.00 -72.00-137.74   52
 46  \w   -135.00-108.00   0.50    0.47    --  -66.00 -72.00  -8.67   54
 47  \w    -79.00 -45.00   0.50    0.47    --  -66.00 -72.00  -8.67   68
 48  \w    -74.00 -48.00   0.50    0.47    --  -70.00 -75.00-147.47   52
 49  \w    -77.00 -51.00   0.50    0.47    --  -70.00 -67.00 -58.33   52
 50  \w    -80.00 -54.00   0.50    0.47    --  -70.00 -61.00-138.42   52
 51  \w    -82.00 -56.00   0.50    0.47    --  -70.00 -62.00  54.76   52
 52  \w    -76.00 -51.00   0.50    1.87    --  -74.00 -76.00 174.80   50
 53  \w    -77.00 -51.00   0.50    1.87    --  -74.00 -76.00  93.85   52
 54  \w    -77.00 -51.00   0.50    1.87    --  -74.00 -76.00-173.43   52
 55  \w    -76.00 -51.00   0.50    1.87    --  -74.00 -77.00 150.51   50
 56  \w    -89.00 -56.00   0.50    1.87    --  -74.00 -73.00  42.36   66
 57  \w    -79.00 -53.00   0.50    1.87    --  -74.00 -74.00  58.07   52
 58  \w    -82.00 -56.00   0.50    1.87    --  -74.00 -67.00 -35.11   52
 59  \w    -83.00 -57.00   0.50    1.87    --  -78.00 -76.00  14.60   52
 60  \w    -90.00 -62.00   0.50    1.87    --  -82.00 -69.00-153.94   56
 61  \w    -91.00 -61.00   0.50    1.87    --  -82.00 -72.00-114.27   60
 62  \w    -88.00 -62.00   0.50    1.87    --  -82.00 -71.00-100.43   52
 63  \w    -90.00 -64.00   0.50    1.87    --  -82.00 -65.00 -82.36   52
 64  \w    -89.00 -64.00   0.50    1.87    --  -82.00 -64.00 -64.71   50
 65  \w    -90.00 -59.00   0.50    1.87    --  -82.00 -76.00-178.47   62
 66  \w    -90.00 -63.00   0.50    1.87    --  -82.00 -68.00-135.90   54
 67  \w    -85.00 -60.00   0.50    1.87    --  -82.00 -75.00  78.11   50
 68  \w   -111.00 -63.00   0.50    1.87    --  -86.00 -77.00 132.46   96
 69  \w   -158.00-120.00   0.50    1.87    --  -86.00 -77.00 132.46   76
 70  \w    -93.00 -63.00   0.50    1.87    --  -86.00 -76.00-161.13   60
 71  \w    -92.00 -64.00   0.50    1.87    --  -86.00 -75.00  66.78   56
 72  \w   -158.00-116.00   0.50    1.87    --  -86.00 -75.00  66.78   84
 73  \w   -126.00 -72.00   0.50    1.87    --  -90.00 -64.00 143.15  108
 74  \w   -160.00 -79.00   0.50    1.87    --  -91.75 -61.00 150.00  162
 75  \w    -98.00 -71.00   0.50    1.87    --  -91.75 -77.00-180.00   54
 76  \w   -142.00-116.00   0.50    1.87    --  -91.75 -77.00-180.00   52
 77  \w   -162.00 -77.00   0.50    1.87    --  -91.75 -65.00 -26.04  170
 78  \w    -70.00 -19.00   0.50    1.87    --  -91.75  61.00 -30.00  102
 79  \w   -104.00 -70.00   0.50    1.87    --  -91.75 -75.00  51.10   68
 80  \w   -152.00-127.00   0.50    1.87    --  -91.75 -74.00  17.11   50
 81  \w   -152.00-126.00   0.50    1.87    --  -91.75 -75.00  51.10   52
 82  \w   -102.00 -71.00   0.50    1.87    --  -91.75 -74.00-107.50   62
 83  \w   -158.00-113.00   0.50    1.87    --  -91.75 -74.00-107.50   90
 84  \w   -100.00 -74.00   0.50    1.87    --  -91.75 -72.00 -75.90   52
 85  \w   -125.00 -74.00   0.50    1.87    --  -91.75 -68.00  28.42  102
 86  \w    -95.00 -69.00   0.50    1.87    --  -91.75 -77.00   0.00   52
 87  \w   -159.00-133.00   0.50    1.87    --  -91.75 -77.00   0.00   52
 88  \w   -163.00 -75.00   0.50    1.87    --  -91.75 -66.00   2.10  176
 89  \w    -97.00 -72.00   0.50    1.87    --  -91.75 -77.00 -90.00   50
 90  \w   -161.00 -73.00   0.50    1.87    --  -91.75 -71.00-163.76  176
 91  \w   -148.00-102.00   0.50    1.87    --  -91.75 -77.00 -90.00   92
 92  \w   -152.00-124.00   0.50    1.87    --  -91.75 -65.00  94.83   56
 93  \w    -46.00 -20.00   0.50    1.87    --  -91.75  45.00 -30.00   52
 94  \w   -126.00 -71.00   0.50    1.87    --  -91.75 -74.00  17.11  110
 95  \w    -98.00 -72.00   0.50    1.87    --  -91.75 -72.00 -28.66   52
 96  \w   -159.00 -75.00   0.50    1.87    --  -91.75 -63.00  83.11  168
 97  \w   -163.00 -70.00   0.50    1.87    --  -91.75 -77.00-125.21  186
 98  \w   -115.00 -76.00   0.50    1.87    --  -91.75 -65.00  94.83   78
 99  \w   -100.00 -71.00   0.50    1.87    --  -91.75 -77.00 -60.00   58
100  \w    -98.00 -71.00   0.50    1.87    --  -91.75 -73.00 -46.10   54
101  \w   -163.00-113.00   0.50    1.87    --  -91.75 -73.00 -46.10  100
102  \w   -154.00-129.00   0.50    1.87    --  -91.75 -67.00 118.08   50
103  \w   -103.00 -77.00   0.50    1.87    --  -91.75 -67.00 118.08   52
104  \w   -161.00-112.00   0.50    1.87    --  -91.75 -77.00 -60.00   98
105  \w    -84.00 -59.00   0.50    1.87    --  -91.75 141.00 117.00   50
106  \w     61.00 112.00   0.50    1.87    --  106.52-126.00   0.00  102
107  \w    106.00 154.00   0.50    1.87    --  106.52 126.00-180.00   96
108  \w     34.00  68.00   0.50    1.87    --  106.52 -61.00-180.00   68
109  \w     43.00 111.00   0.50    1.87    --  106.52-126.00 150.00  136
110  \w     46.00  97.00   0.50    1.87    --  106.52 -95.00 -90.00  102
111  \w     57.00 108.00   0.50    1.87    --  106.52-126.00 -90.00  102
112  \w     34.00  71.00   0.50    1.87    --  106.52 -61.00 120.00   74
113  \w     72.00 108.00   0.50    1.87    --  106.52-113.00  74.39   72
114  \w     51.00  93.00   0.50    1.87    --  106.52 -77.00 120.00   84
115  \w     45.00  70.00   0.50    1.87    --  106.52-113.00  74.39   50
116  \w     37.00  70.00   0.50    1.87    --  106.52 -61.00-150.00   66
117  \w     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       '\w 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+0.001xFc^2^\l^3^/sin(2\q)]^-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/[\s^2^(Fo^2^)+(0.0937P)^2^+0.1979P] where P=(Fo^2^+2Fc^2^)/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 > 2\s(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_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
_shelx_res_checksum              53997
_shelx_hkl_checksum              24756
_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