Structural elucidation of 1-(3-acetyl-2,6-dihydroxy-4-methoxyphenyl)-4,5-dihydroxy-2-methylanthracene-9,10-dione isolated from Bulbine latifolia (L.) Wild, C24H18O8
Hlangothi, Buyiswa G.; Mahanjana, Lungelwa; Hosten, Eric C.; van Heerden, Fanie R.; van de Venter, Maryna; Zeitschrift für Kristallographie - New Crystal Structures 235 (2020) 1077–1081; doi:10.1515/ncrs-2020-0177

data_8105383
_publ_section_title
;
 Structural elucidation of
 1-(3-acetyl-2,6-dihydroxy-4-methoxyphenyl)-4,5-dihydroxy-2-methylanthracene-9,10-dione
 isolated from Bulbine latifolia (L.) Wild, C24H18O8
;
_journal_issue                   5
_journal_name_full
'Zeitschrift f\"ur Kristallographie - New Crystal Structures'
_journal_page_first              1077
_journal_page_last               1081
_journal_paper_doi               10.1515/ncrs-2020-0177
_journal_volume                  235
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H18 O8'
_chemical_formula_sum            'C24 H18 O8'
_chemical_formula_weight         434.38
_chemical_melting_point          512.15
_chemical_name_common            Knipholone
_chemical_name_systematic
;
1-(3-acetyl-2,6-dihydroxy-4-methoxyphenyl)-4,5-dihydroxy-2-methylanthraquinone
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 96.777(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.9654(3)
_cell_length_b                   23.6910(8)
_cell_length_c                   21.2314(8)
_cell_measurement_reflns_used    9956
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      27.90
_cell_measurement_theta_min      2.58
_cell_volume                     3978.5(3)
_computing_cell_refinement       'APEX2 v2011.4-1 [1]'
_computing_data_collection       'Bruker Instrument Service v2011.4.0.0 [1]'
_computing_data_reduction        'SAINT V7.68A [1]'
_computing_molecular_graphics    'Ortep-3 for Windows [5]'
_computing_publication_material  'PLATON [6] and MERCURY [7]'
_computing_structure_refinement  'SHELXL 2018/3 [3] and ShelXle [4]'
_computing_structure_solution    'SHELXT 2018/2 [2]'
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w 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  0.0246
_diffrn_reflns_av_unetI/netI     0.0411
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            36555
_diffrn_reflns_point_group_measured_fraction_full 0.920
_diffrn_reflns_point_group_measured_fraction_max 0.890
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.386
_diffrn_reflns_theta_min         1.932
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8735
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS V2008/1 [1]'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1808
_exptl_crystal_size_max          0.525
_exptl_crystal_size_mid          0.467
_exptl_crystal_size_min          0.066
_refine_diff_density_max         0.281
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
;
 Flack x determined using 5306 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1181
_refine_ls_number_reflns         17766
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0647
_refine_ls_R_factor_gt           0.0499
_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/[\s^2^(Fo^2^)+(0.0661P)^2^+1.0201P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1238
_refine_ls_wR_factor_ref         0.1320
_reflns_Friedel_coverage         0.767
_reflns_Friedel_fraction_full    0.841
_reflns_Friedel_fraction_max     0.791
_reflns_number_gt                14484
_reflns_number_total             17766
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            suppl_ncrs-2020-0177_suppl.cif
_cod_data_source_block           ea110
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               8105383
_shelx_estimated_absorpt_t_min   0.944
_shelx_estimated_absorpt_t_max   0.993