##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section C. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section C, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_database_code_depnum_ccdc_archive 'CCDC 1446723'
_audit_creation_method     'SHELXL-2014/7'
_journal_date_recd_electronic     2015-09-30
_journal_date_accepted     2016-01-12
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2016
_journal_volume     72
_journal_issue      2
_journal_page_first     124
_journal_page_last     127
_journal_paper_category     FA
_journal_paper_doi     10.1107/S2053229616000577
_journal_coeditor_code     YO3016
_publ_contact_author_name     'Shigeru Itai'
_publ_contact_author_address
;
Graduate Division of Pharmaceutical Sciences, University of Shizuoka,
52-1 Yada, Suruga-Ku, Shizuoka, Japan
;
_publ_contact_author_email     s-itai@u-shizuoka-ken.ac.jp
_publ_contact_author_fax     '+81-54-264-5615'
_publ_contact_author_phone     '+81-54-264-5614'
_publ_section_title
;
Nobiletin: a citrus flavonoid displaying potent physiological activity
;
_publ_section_title_footnote     .
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Noguchi, Shuji' .
;
Graduate Division of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada,
Suruga-Ku, Shizuoka, Japan
;
    'Atsumi, Haruka' .
;
Graduate Division of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada,
Suruga-Ku, Shizuoka, Japan
;
    'Iwao, Yasunori' .
;
Graduate Division of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada,
Suruga-Ku, Shizuoka, Japan
;
    'Kan, Toshiyuki' .
;
Graduate Division of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada,
Suruga-Ku, Shizuoka, Japan
;
    'Itai, Shigeru' .
;
Graduate Division of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada,
Suruga-Ku, Shizuoka, Japan
;
_publ_section_synopsis
;
Based on its potent physiological activities, the citrus flavonoid nobiletin
has become an attractive candidate for use as a therapeutic agent. The crystal
structure analysis revealed it to be nobiletin is conformationally chiral
because of the conformational arrangement of the four methoxy groups bound to
the chromene ring of the flavone moiety.
;
_chemical_name_systematic
;
2-(3,4-Dimethoxyphenyl)-5,6,7,8-tetramethoxy-4H-chromen-4-one
;
_chemical_name_common
;
Nobiletin
;
_chemical_formula_moiety     'C21 H22 O8'
_chemical_formula_sum     'C21 H22 O8'
_chemical_formula_iupac     'C21 H22 O8'
_chemical_formula_weight     402.38
_chemical_melting_point     ?
_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.
;
_space_group_crystal_system     orthorhombic
_space_group_name_H-M_alt     'P 21 21 21'
_space_group_name_Hall     'P 2ac 2ab'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x+1/2, -y, z+1/2'
    '-x, y+1/2, -z+1/2'
    'x+1/2, -y+1/2, -z'
_cell_length_a     19.3239(17)
_cell_length_b     22.921(2)
_cell_length_c     4.1385(4)
_cell_angle_alpha     90
_cell_angle_beta     90
_cell_angle_gamma     90
_cell_volume     1833.0(3)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     377
_cell_measurement_theta_min     2.81
_cell_measurement_theta_max     29.5
_cell_measurement_temperature     100(2)
_exptl_crystal_description     'column'
_exptl_crystal_colour     'colourless'
_exptl_crystal_size_max     0.5
_exptl_crystal_size_mid     0.02
_exptl_crystal_size_min     0.01
_exptl_crystal_density_diffrn     1.458
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     848
_exptl_absorpt_coefficient_mu     0.112
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_shelx_estimated_absorpt_T_min     ?
_shelx_estimated_absorpt_T_max     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_diffrn_ambient_temperature     100(2)
_diffrn_radiation_type     'Synchrotron (SPring-8 BL02B1)'
_diffrn_radiation_wavelength     0.70041
_diffrn_measurement_device_type     'Rigaku Mercury2 CCD four-circle'
_diffrn_measurement_method     'ω scan'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     13177
_diffrn_reflns_av_R_equivalents     0.0425
_diffrn_reflns_theta_min     1.358
_diffrn_reflns_theta_max     29.604
_diffrn_reflns_theta_full     24.850
_diffrn_measured_fraction_theta_max     0.937
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -26
_diffrn_reflns_limit_h_max     25
_diffrn_reflns_limit_k_min     -32
_diffrn_reflns_limit_k_max     30
_diffrn_reflns_limit_l_min     -5
_diffrn_reflns_limit_l_max     5
_refine_special_details     ?
_reflns_number_total     4894
_reflns_number_gt     4091
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0805
_refine_ls_R_factor_gt     0.0651
_refine_ls_wR_factor_gt     0.1854
_refine_ls_wR_factor_ref     0.1915
_refine_ls_goodness_of_fit_ref     1.294
_refine_ls_restrained_S_all     1.294
_refine_ls_number_reflns     4894
_refine_ls_number_parameters     268
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                      'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.418
_refine_diff_density_min     -0.289
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
_refine_ls_abs_structure_details
                              'An arbitrary choice of enantiomer has been made.'
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0020 0.0016
                         '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' 0.0075 0.0059
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection
;
RAPID-AUTO (Rigaku, 2010)
;
_computing_cell_refinement
;
RAPID-AUTO (Rigaku, 2010)
;
_computing_data_reduction
;
RAPID-AUTO (Rigaku, 2010)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b) and
shelXle (Hübschle et al.,  2011)
;
_computing_molecular_graphics
;
Mercury (Macrae et al.,  2008)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    O O2 0.86158(13) 0.29414(11) 0.2767(8) 0.0202(6) Uani d 1 . .
    C C2 0.70156(19) 0.36216(16) 0.4652(10) 0.0159(7) Uani d 1 . .
    O O1 0.66854(13) 0.32043(11) 0.6357(7) 0.0166(6) Uani d 1 . .
    O O3 0.85629(13) 0.18115(11) 0.5377(7) 0.0165(6) Uani d 1 . .
    C C3 0.76441(19) 0.35347(16) 0.3380(11) 0.0178(8) Uani d 1 . .
    H H3 0.7845 0.3837 0.2118 0.021 Uiso calc 1 . .
    O O4 0.77681(14) 0.10365(12) 0.8750(7) 0.0196(6) Uani d 1 . .
    C C4 0.80334(18) 0.29972(16) 0.3846(10) 0.0157(7) Uani d 1 . .
    C C7 0.68406(19) 0.17222(16) 0.8978(10) 0.0160(7) Uani d 1 . .
    O O7 0.49217(13) 0.47574(11) 0.7082(8) 0.0213(7) Uani d 1 . .
    O O6 0.59535(14) 0.24399(13) 0.9566(8) 0.0218(6) Uani d 1 . .
    C C6 0.7513(2) 0.15775(15) 0.7931(10) 0.0164(8) Uani d 1 . .
    O O5 0.64380(15) 0.13367(12) 1.0635(8) 0.0247(7) Uani d 1 . .
    C C5 0.79098(18) 0.19812(16) 0.6319(10) 0.0154(7) Uani d 1 . .
    C C9 0.69935(18) 0.26729(15) 0.6807(10) 0.0147(7) Uani d 1 . .
    O O8 0.53896(14) 0.56400(12) 0.4006(8) 0.0220(6) Uani d 1 . .
    C C8 0.65893(18) 0.22752(17) 0.8452(10) 0.0161(8) Uani d 1 . .
    C C10 0.76586(18) 0.25431(16) 0.5686(10) 0.0143(7) Uani d 1 . .
    C C17 0.90960(18) 0.20222(16) 0.7489(10) 0.0172(8) Uani d 1 . .
    H H17A 0.9536 0.1834 0.6937 0.021 Uiso calc 1 . .
    H H17B 0.8975 0.1930 0.9731 0.021 Uiso calc 1 . .
    H H17C 0.9141 0.2446 0.7240 0.021 Uiso calc 1 . .
    C C11 0.66062(19) 0.41593(16) 0.4440(10) 0.0164(7) Uani d 1 . .
    C C18 0.7924(2) 0.06551(17) 0.6135(12) 0.0259(9) Uani d 1 . .
    H H18A 0.7526 0.0634 0.4673 0.031 Uiso calc 1 . .
    H H18B 0.8027 0.0265 0.6977 0.031 Uiso calc 1 . .
    H H18C 0.8327 0.0804 0.4956 0.031 Uiso calc 1 . .
    C C12 0.59492(19) 0.41848(16) 0.5923(10) 0.0169(8) Uani d 1 . .
    H H12 0.5775 0.3855 0.7054 0.020 Uiso calc 1 . .
    C C19 0.6239(2) 0.08263(18) 0.8898(14) 0.0314(11) Uani d 1 . .
    H H19A 0.6101 0.0935 0.6700 0.038 Uiso calc 1 . .
    H H19B 0.5849 0.0639 0.9999 0.038 Uiso calc 1 . .
    H H19C 0.6630 0.0555 0.8802 0.038 Uiso calc 1 . .
    C C13 0.55586(19) 0.46892(16) 0.5732(11) 0.0176(8) Uani d 1 . .
    C C20 0.5402(2) 0.2274(2) 0.7441(13) 0.0325(11) Uani d 1 . .
    H H20A 0.5338 0.1850 0.7530 0.039 Uiso calc 1 . .
    H H20B 0.5516 0.2390 0.5226 0.039 Uiso calc 1 . .
    H H20C 0.4973 0.2467 0.8115 0.039 Uiso calc 1 . .
    C C14 0.58174(19) 0.51748(16) 0.4071(11) 0.0178(8) Uani d 1 . .
    C C15 0.64615(19) 0.51500(16) 0.2609(10) 0.0179(8) Uani d 1 . .
    H H15 0.6635 0.5480 0.1478 0.021 Uiso calc 1 . .
    C C16 0.68554(19) 0.46417(16) 0.2797(11) 0.0183(8) Uani d 1 . .
    H H16 0.7297 0.4626 0.1793 0.022 Uiso calc 1 . .
    C C21 0.4644(2) 0.42762(18) 0.8763(12) 0.0229(9) Uani d 1 . .
    H H21A 0.4580 0.3950 0.7263 0.027 Uiso calc 1 . .
    H H21B 0.4197 0.4385 0.9704 0.027 Uiso calc 1 . .
    H H21C 0.4963 0.4160 1.0488 0.027 Uiso calc 1 . .
    C C22 0.5608(2) 0.61381(17) 0.2152(12) 0.0234(9) Uani d 1 . .
    H H22A 0.5690 0.6020 -0.0091 0.028 Uiso calc 1 . .
    H H22B 0.6036 0.6296 0.3072 0.028 Uiso calc 1 . .
    H H22C 0.5246 0.6438 0.2213 0.028 Uiso calc 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    O2 C4 . 1.217(4) ?
    C2 C3 . 1.339(5) ?
    C2 O1 . 1.349(4) ?
    C2 C11 . 1.467(5) ?
    O1 C9 . 1.368(4) ?
    O3 C5 . 1.377(4) ?
    O3 C17 . 1.435(5) ?
    C3 C4 . 1.456(5) ?
    C3 H3 . 0.9500 ?
    O4 C6 . 1.376(4) ?
    O4 C18 . 1.424(5) ?
    C4 C10 . 1.479(5) ?
    C7 O5 . 1.362(5) ?
    C7 C8 . 1.375(5) ?
    C7 C6 . 1.410(5) ?
    O7 C13 . 1.361(4) ?
    O7 C21 . 1.410(5) ?
    O6 C8 . 1.365(4) ?
    O6 C20 . 1.434(5) ?
    C6 C5 . 1.374(5) ?
    O5 C19 . 1.426(5) ?
    C5 C10 . 1.401(5) ?
    C9 C8 . 1.380(5) ?
    C9 C10 . 1.398(5) ?
    O8 C14 . 1.349(4) ?
    O8 C22 . 1.439(5) ?
    C17 H17A . 0.9800 ?
    C17 H17B . 0.9800 ?
    C17 H17C . 0.9800 ?
    C11 C16 . 1.384(5) ?
    C11 C12 . 1.411(5) ?
    C18 H18A . 0.9800 ?
    C18 H18B . 0.9800 ?
    C18 H18C . 0.9800 ?
    C12 C13 . 1.383(5) ?
    C12 H12 . 0.9500 ?
    C19 H19A . 0.9800 ?
    C19 H19B . 0.9800 ?
    C19 H19C . 0.9800 ?
    C13 C14 . 1.401(5) ?
    C20 H20A . 0.9800 ?
    C20 H20B . 0.9800 ?
    C20 H20C . 0.9800 ?
    C14 C15 . 1.385(5) ?
    C15 C16 . 1.394(5) ?
    C15 H15 . 0.9500 ?
    C16 H16 . 0.9500 ?
    C21 H21A . 0.9800 ?
    C21 H21B . 0.9800 ?
    C21 H21C . 0.9800 ?
    C22 H22A . 0.9800 ?
    C22 H22B . 0.9800 ?
    C22 H22C . 0.9800 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C3 C2 O1 . . 122.0(3) ?
    C3 C2 C11 . . 126.2(4) ?
    O1 C2 C11 . . 111.8(3) ?
    C2 O1 C9 . . 119.8(3) ?
    C5 O3 C17 . . 113.0(3) ?
    C2 C3 C4 . . 122.8(4) ?
    C2 C3 H3 . . 118.6 ?
    C4 C3 H3 . . 118.6 ?
    C6 O4 C18 . . 116.2(3) ?
    O2 C4 C3 . . 121.2(3) ?
    O2 C4 C10 . . 124.6(3) ?
    C3 C4 C10 . . 114.2(3) ?
    O5 C7 C8 . . 118.4(3) ?
    O5 C7 C6 . . 121.9(3) ?
    C8 C7 C6 . . 119.6(3) ?
    C13 O7 C21 . . 117.2(3) ?
    C8 O6 C20 . . 112.9(3) ?
    C5 C6 O4 . . 121.8(3) ?
    C5 C6 C7 . . 120.3(3) ?
    O4 C6 C7 . . 117.8(3) ?
    C7 O5 C19 . . 115.6(3) ?
    C6 C5 O3 . . 117.3(3) ?
    C6 C5 C10 . . 121.1(3) ?
    O3 C5 C10 . . 121.6(3) ?
    O1 C9 C8 . . 114.1(3) ?
    O1 C9 C10 . . 123.0(3) ?
    C8 C9 C10 . . 122.9(3) ?
    C14 O8 C22 . . 117.3(3) ?
    O6 C8 C7 . . 121.3(3) ?
    O6 C8 C9 . . 119.6(3) ?
    C7 C8 C9 . . 119.2(3) ?
    C9 C10 C5 . . 116.9(3) ?
    C9 C10 C4 . . 118.1(3) ?
    C5 C10 C4 . . 125.0(3) ?
    O3 C17 H17A . . 109.5 ?
    O3 C17 H17B . . 109.5 ?
    H17A C17 H17B . . 109.5 ?
    O3 C17 H17C . . 109.5 ?
    H17A C17 H17C . . 109.5 ?
    H17B C17 H17C . . 109.5 ?
    C16 C11 C12 . . 119.6(3) ?
    C16 C11 C2 . . 120.8(3) ?
    C12 C11 C2 . . 119.6(3) ?
    O4 C18 H18A . . 109.5 ?
    O4 C18 H18B . . 109.5 ?
    H18A C18 H18B . . 109.5 ?
    O4 C18 H18C . . 109.5 ?
    H18A C18 H18C . . 109.5 ?
    H18B C18 H18C . . 109.5 ?
    C13 C12 C11 . . 120.0(3) ?
    C13 C12 H12 . . 120.0 ?
    C11 C12 H12 . . 120.0 ?
    O5 C19 H19A . . 109.5 ?
    O5 C19 H19B . . 109.5 ?
    H19A C19 H19B . . 109.5 ?
    O5 C19 H19C . . 109.5 ?
    H19A C19 H19C . . 109.5 ?
    H19B C19 H19C . . 109.5 ?
    O7 C13 C12 . . 124.5(3) ?
    O7 C13 C14 . . 115.7(3) ?
    C12 C13 C14 . . 119.8(3) ?
    O6 C20 H20A . . 109.5 ?
    O6 C20 H20B . . 109.5 ?
    H20A C20 H20B . . 109.5 ?
    O6 C20 H20C . . 109.5 ?
    H20A C20 H20C . . 109.5 ?
    H20B C20 H20C . . 109.5 ?
    O8 C14 C15 . . 125.1(4) ?
    O8 C14 C13 . . 114.8(3) ?
    C15 C14 C13 . . 120.2(3) ?
    C14 C15 C16 . . 120.0(4) ?
    C14 C15 H15 . . 120.0 ?
    C16 C15 H15 . . 120.0 ?
    C11 C16 C15 . . 120.3(3) ?
    C11 C16 H16 . . 119.8 ?
    C15 C16 H16 . . 119.8 ?
    O7 C21 H21A . . 109.5 ?
    O7 C21 H21B . . 109.5 ?
    H21A C21 H21B . . 109.5 ?
    O7 C21 H21C . . 109.5 ?
    H21A C21 H21C . . 109.5 ?
    H21B C21 H21C . . 109.5 ?
    O8 C22 H22A . . 109.5 ?
    O8 C22 H22B . . 109.5 ?
    H22A C22 H22B . . 109.5 ?
    O8 C22 H22C . . 109.5 ?
    H22A C22 H22C . . 109.5 ?
    H22B C22 H22C . . 109.5 ?
