Synthesis and crystal structure of 5,10-dihy-droxy-9-meth-oxy-2,2-dimethyl-12-(2-methyl-but-3-en-2-yl)-2<i>H</i>,6<i>H</i>-pyrano[3,2-<i>b</i>]xanthen-6-one.
Saekee, Amporn; Kuhakarn, Chutima; Chakarawet, Khetpakorn; Hongthong, Sakchai; Acta crystallographica. Section E, Crystallographic communications 81 (2025) 219–223; doi:10.1107/S2056989025001070

data_2023404
_publ_section_title
;
 Synthesis and crystal structure of
 5,10-dihy-droxy-9-meth-oxy-2,2-dimethyl-12-(2-methyl-but-3-en-2-yl)-2<i>H</i>,6<i>H</i>-pyrano[3,2-<i>b</i>]xanthen-6-one.
;
_journal_coeditor_code           DX2063
_journal_issue                   'Pt 3'
_journal_name_full
'Acta crystallographica. Section E, Crystallographic communications'
_journal_page_first              219
_journal_page_last               223
_journal_paper_doi               10.1107/S2056989025001070
_journal_volume                  81
_journal_year                    2025
_chemical_formula_iupac          'C24 H24 O6'
_chemical_formula_moiety         'C24 H24 O6'
_chemical_formula_sum            'C24 H24 O6'
_chemical_formula_weight         408.43
_chemical_name_common            'Garciosone F'
_chemical_name_systematic
5,10-Dihydroxy-9-methoxy-2,2-dimethyl-12-(2-methylbut-3-en-2-yl)-2H,6H-pyrano[3,2-b]xanthen-6-one
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_cell_angle_alpha                90
_cell_angle_beta                 96.2090(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.6205(3)
_cell_length_b                   14.8160(4)
_cell_length_c                   12.7073(3)
_cell_measurement_reflns_used    9895
_cell_measurement_temperature    101.00
_cell_measurement_theta_max      68.472
_cell_measurement_theta_min      4.600
_cell_volume                     1987.81(9)
_computing_cell_refinement
;
SAINT V8.40B (Bruker, 2016)
;
_computing_data_collection
;
APEX2 (Bruker, 2016)
;
_computing_data_reduction
;
SAINT V8.40B (Bruker, 2016)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
Olex2 1.5 (Dolomanov <i>et al.</i>,  2009)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL  (Sheldrick, 2015b)
;
_computing_structure_solution
;
<i>SHELXT2015</i> (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      101.00
_diffrn_detector                 'Bruker PHOTON III detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON III C7'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            32650
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.548
_diffrn_reflns_theta_min         4.187
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.1
_diffrn_source_power             0.55000000000000E-1
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.804
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.7032
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause <i>et al.</i>,  2015)
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.175
_exptl_crystal_size_mid          0.108
_exptl_crystal_size_min          0.059
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.245
_refine_ls_abs_structure_details
;
Flack <i>x</i> determined using 3110 quotients
[(<i>I</i>^+^)-(<i>I</i>^-^)]/[(<i>I</i>^+^)+(<i>I</i>^-^)]
(Parsons <i>et al.</i>, 2013)
;
_refine_ls_abs_structure_Flack   0.00(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     581
_refine_ls_number_reflns         7256
_refine_ls_number_restraints     253
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0308
_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^)+(0.0448P)^2^+0.2292P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0777
_refine_ls_wR_factor_ref         0.0791
_reflns_number_gt                6891
_reflns_number_total             7256
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            dx2063.cif
_cod_data_source_block           I
_cod_depositor_comments          'Adding full bibliography for 2023404.cif.'
_cod_database_code               2023404
_shelx_estimated_absorpt_t_min   0.872
_shelx_estimated_absorpt_t_max   0.954
_shelx_hkl_checksum              87734
_shelx_res_checksum              71361