Nobiletin: a citrus flavonoid displaying potent physiological activity
Noguchi, Shuji; Atsumi, Haruka; Iwao, Yasunori; Kan, Toshiyuki; Itai, Shigeru; Acta Crystallographica Section C 72 (2016) 124–127; doi:10.1107/S2053229616000577

data_2020390
_publ_section_title
;
 Nobiletin: a citrus flavonoid displaying potent physiological activity
;
_journal_coeditor_code           YO3016
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              124
_journal_page_last               127
_journal_paper_doi               10.1107/S2053229616000577
_journal_volume                  72
_journal_year                    2016
_chemical_formula_iupac          'C21 H22 O8'
_chemical_formula_moiety         'C21 H22 O8'
_chemical_formula_sum            'C21 H22 O8'
_chemical_formula_weight         402.38
_chemical_name_common
;
Nobiletin
;
_chemical_name_systematic
;
2-(3,4-Dimethoxyphenyl)-5,6,7,8-tetramethoxy-4<i>H</i>-chromen-4-one
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.3239(17)
_cell_length_b                   22.921(2)
_cell_length_c                   4.1385(4)
_cell_measurement_reflns_used    377
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.5
_cell_measurement_theta_min      2.81
_cell_volume                     1833.0(3)
_computing_cell_refinement
;
RAPID-AUTO (Rigaku, 2010)
;
_computing_data_collection
;
RAPID-AUTO (Rigaku, 2010)
;
_computing_data_reduction
;
RAPID-AUTO (Rigaku, 2010)
;
_computing_molecular_graphics
;
Mercury (Macrae <i>et al.</i>,  2008)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015<i>b</i>) and
<i>shelXle</i> (H\"ubschle <i>et al.</i>,  2011)
;
_computing_structure_solution
;
<i>SHELXT</i> (Sheldrick, 2015<i>a</i>)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.937
_diffrn_measurement_device_type  'Rigaku Mercury2 CCD four-circle'
_diffrn_measurement_method       '\w scan'
_diffrn_radiation_type           'Synchrotron (SPring-8 BL02B1)'
_diffrn_radiation_wavelength     0.70041
_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            13177
_diffrn_reflns_theta_full        24.850
_diffrn_reflns_theta_max         29.604
_diffrn_reflns_theta_min         1.358
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_description       column
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.418
_refine_diff_density_min         -0.289
_refine_ls_abs_structure_details
'An arbitrary choice of enantiomer has been made.'
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.294
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     268
_refine_ls_number_reflns         4894
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.294
_refine_ls_R_factor_all          0.0805
_refine_ls_R_factor_gt           0.0651
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1854
_refine_ls_wR_factor_ref         0.1915
_reflns_number_gt                4091
_reflns_number_total             4894
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            yo3016sup1.cif
_cod_data_source_block           I
_cod_depositor_comments          'Adding full bibliography for 2020390.cif.'
_cod_database_code               2020390
_cod_database_fobs_code          2020390
_shelx_hkl_checksum              30106
_shelx_res_checksum              66047