#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/98/2229881.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2229881
loop_
_publ_author_name
'Zhang, Yu'
'Zhang, Yi-Nan'
'Liu, Ming-Ming'
'Ryu, Kum-Chol'
'Ye, De-Yong'
_publ_section_title
;
 (E)-3-(8-Benzyloxy-2,3-dihydro-1,4-benzodioxin-6-yl)-1-[2-hydroxy-4,6-bis(methoxymethoxy)phenyl]prop-2-en-1-one
;
_journal_coeditor_code           XU5171
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o912
_journal_page_last               o913
_journal_paper_doi               10.1107/S160053681100924X
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C28 H28 O9'
_chemical_formula_moiety         'C28 H28 O9'
_chemical_formula_sum            'C28 H28 O9'
_chemical_formula_weight         508.50
_chemical_name_systematic
;
(E)-3-(8-Benzyloxy-2,3-dihydro-1,4-benzodioxin-6-yl)-
1-[2-hydroxy-4,6-bis(methoxymethoxy)phenyl]prop-2-en-1-one
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                72.752(5)
_cell_angle_beta                 84.269(5)
_cell_angle_gamma                70.601(5)
_cell_formula_units_Z            2
_cell_length_a                   8.149(4)
_cell_length_b                   11.744(5)
_cell_length_c                   14.439(7)
_cell_measurement_reflns_used    847
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      27.124
_cell_measurement_theta_min      2.649
_cell_volume                     1244.8(10)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'Bruker CCD 1000 area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_sigmaI/netI    0.0348
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5687
_diffrn_reflns_theta_full        26.01
_diffrn_reflns_theta_max         26.01
_diffrn_reflns_theta_min         1.48
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.9820
_exptl_absorpt_correction_T_min  0.9653
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.600
_refine_diff_density_min         -0.207
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     353
_refine_ls_number_reflns         4774
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0820
_refine_ls_R_factor_gt           0.0607
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1260P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1784
_refine_ls_wR_factor_ref         0.1946
_reflns_number_gt                3239
_reflns_number_total             4774
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            xu5171.cif
_cod_data_source_block           I
_cod_original_cell_volume        1244.7(10)
_cod_database_code               2229881
_cod_database_fobs_code          2229881
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 -0.02313(19) 0.61404(14) 0.91280(12) 0.0582(5) Uani d . 1 . .
O O2 -0.2521(2) 0.86192(14) 0.83479(12) 0.0597(5) Uani d . 1 . .
O O3 0.29103(19) 0.54252(13) 0.84269(11) 0.0558(5) Uani d . 1 A .
O O4 0.3240(2) 1.09630(15) 0.44508(13) 0.0642(5) Uani d . 1 . .
O O5 -0.1587(2) 1.65623(15) 0.28563(12) 0.0647(5) Uani d . 1 . .
O O6 -0.2044(3) 1.83191(15) 0.15912(13) 0.0736(5) Uani d . 1 . .
O O7 -0.1328(2) 1.30029(15) 0.55058(12) 0.0659(5) Uani d . 1 . .
O O8 -0.4304(3) 1.35542(18) 0.53966(16) 0.0848(6) Uani d . 1 . .
O O9 0.3228(2) 1.28722(16) 0.31656(13) 0.0668(5) Uani d . 1 . .
H H9C 0.3572 1.2137 0.3494 0.100 Uiso calc R 1 . .
C C1 -0.172(2) 0.6699(16) 0.9639(10) 0.086(4) Uani d P 0.463(18) A 1
H H1A -0.2494 0.6200 0.9719 0.103 Uiso calc PR 0.463(18) A 1
H H1B -0.1333 0.6586 1.0283 0.103 Uiso calc PR 0.463(18) A 1
C C2 -0.2644(15) 0.7837(9) 0.9331(7) 0.057(2) Uani d P 0.463(18) A 1
H H2A -0.2440 0.8268 0.9765 0.069 Uiso calc PR 0.463(18) A 1
H H2B -0.3847 0.7855 0.9424 0.069 Uiso calc PR 0.463(18) A 1
C C1' -0.2038(13) 0.6528(9) 0.9316(8) 0.054(2) Uani d P 0.537(18) A 2
H H1'1 -0.2492 0.5982 0.9103 0.065 Uiso calc PR 0.537(18) A 2
H H1'2 -0.2150 0.6304 1.0017 0.065 Uiso calc PR 0.537(18) A 2
C C2' -0.3120(14) 0.7637(13) 0.9008(13) 0.110(5) Uani d P 0.537(18) A 2
H H2'1 -0.3615 0.7923 0.9570 0.132 Uiso calc PR 0.537(18) A 2
H H2'2 -0.4062 0.7567 0.8690 0.132 Uiso calc PR 0.537(18) A 2
C C3 -0.0883(3) 0.82076(19) 0.79882(16) 0.0448(5) Uani d . 1 A .
C C4 0.0230(3) 0.69963(18) 0.83660(15) 0.0443(5) Uani d . 1 A .
C C5 0.1907(3) 0.66401(18) 0.79889(16) 0.0451(5) Uani d . 1 . .
C C6 0.2440(3) 0.74792(19) 0.72391(16) 0.0474(5) Uani d . 1 A .
H H6A 0.3559 0.7236 0.6991 0.057 Uiso calc R 1 . .
C C7 0.1314(3) 0.86943(18) 0.68465(15) 0.0432(5) Uani d . 1 . .
C C8 -0.0349(3) 0.90484(19) 0.72278(16) 0.0458(5) Uani d . 1 A .
H H8A -0.1109 0.9854 0.6971 0.055 Uiso calc R 1 . .
C C9 0.4658(3) 0.5063(2) 0.8107(2) 0.0668(7) Uani d . 1 . .
H H9A 0.5240 0.5615 0.8209 0.080 Uiso calc R 1 A .
H H9B 0.4686 0.5137 0.7419 0.080 Uiso calc R 1 . .
C C10 0.5581(3) 0.3732(2) 0.86577(16) 0.0493(6) Uani d . 1 A .
C C11 0.5419(3) 0.2761(2) 0.83868(17) 0.0581(6) Uani d . 1 . .
H H11A 0.4675 0.2931 0.7880 0.070 Uiso calc R 1 A .
C C12 0.6339(4) 0.1524(2) 0.8848(2) 0.0697(7) Uani d . 1 A .
H H12A 0.6209 0.0874 0.8651 0.084 Uiso calc R 1 . .
C C13 0.7425(4) 0.1264(2) 0.9585(2) 0.0699(8) Uani d . 1 . .
H H13A 0.8061 0.0434 0.9885 0.084 Uiso calc R 1 A .
C C14 0.7594(4) 0.2206(3) 0.9891(2) 0.0758(8) Uani d . 1 A .
H H14A 0.8328 0.2021 1.0406 0.091 Uiso calc R 1 . .
C C15 0.6664(3) 0.3454(2) 0.9430(2) 0.0663(7) Uani d . 1 . .
H H15A 0.6772 0.4100 0.9642 0.080 Uiso calc R 1 A .
C C16 0.1943(3) 0.95607(19) 0.60541(15) 0.0453(5) Uani d . 1 A .
H H16A 0.3115 0.9287 0.5893 0.054 Uiso calc R 1 . .
C C17 0.1011(3) 1.06911(19) 0.55476(16) 0.0478(5) Uani d . 1 . .
H H17A -0.0167 1.0994 0.5686 0.057 Uiso calc R 1 A .
C C18 0.1795(3) 1.1487(2) 0.47661(16) 0.0458(5) Uani d . 1 A .
C C19 0.0915(3) 1.28298(19) 0.43388(15) 0.0431(5) Uani d . 1 . .
C C20 -0.0676(3) 1.35676(19) 0.46461(15) 0.0461(5) Uani d . 1 A .
C C21 -0.1479(3) 1.4795(2) 0.41326(16) 0.0510(6) Uani d . 1 . .
H H21A -0.2552 1.5247 0.4335 0.061 Uiso calc R 1 A .
C C22 -0.0687(3) 1.53574(19) 0.33120(16) 0.0487(5) Uani d . 1 A .
C C23 0.0905(3) 1.4708(2) 0.30072(16) 0.0528(6) Uani d . 1 . .
H H23A 0.1448 1.5100 0.2470 0.063 Uiso calc R 1 A .
C C24 0.1693(3) 1.3463(2) 0.35090(15) 0.0473(5) Uani d . 1 A .
C C25 -0.0851(4) 1.7180(3) 0.19855(19) 0.0734(8) Uani d . 1 . .
H H25A 0.0211 1.7290 0.2134 0.088 Uiso calc R 1 . .
H H25B -0.0575 1.6677 0.1531 0.088 Uiso calc R 1 . .
C C26 -0.2259(6) 1.9197(3) 0.2108(3) 0.1194(14) Uani d . 1 . .
H H26A -0.3122 1.9971 0.1795 0.179 Uiso calc R 1 . .
H H26B -0.1174 1.9344 0.2126 0.179 Uiso calc R 1 . .
H H26C -0.2627 1.8876 0.2758 0.179 Uiso calc R 1 . .
C C27 -0.2982(3) 1.3618(2) 0.5841(2) 0.0680(7) Uani d . 1 . .
H H27A -0.3059 1.3242 0.6533 0.082 Uiso calc R 1 . .
H H27B -0.3094 1.4495 0.5740 0.082 Uiso calc R 1 . .
C C28 -0.4456(5) 1.2299(3) 0.5652(3) 0.0982(11) Uani d . 1 . .
H H28A -0.5417 1.2315 0.5308 0.147 Uiso calc R 1 . .
H H28B -0.4649 1.2023 0.6337 0.147 Uiso calc R 1 . .
H H28C -0.3402 1.1729 0.5478 0.147 Uiso calc R 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
C4 O1 C1' . . 112.0(4) ?
C4 O1 C1 . . 113.1(6) ?
C1' O1 C1 . . 26.9(7) ?
C3 O2 C2' . . 114.7(5) ?
C3 O2 C2 . . 110.1(5) ?
C2' O2 C2 . . 30.5(7) ?
C5 O3 C9 . . 116.05(16) ?
C22 O5 C25 . . 117.68(19) ?
C25 O6 C26 . . 113.9(3) ?
C20 O7 C27 . . 120.56(18) ?
C27 O8 C28 . . 113.5(2) ?
C24 O9 H9C . . 109.5 ?
C2 C1 O1 . . 122.3(10) ?
C2 C1 H1A . . 106.8 ?
O1 C1 H1A . . 106.8 ?
C2 C1 H1B . . 106.8 ?
O1 C1 H1B . . 106.8 ?
H1A C1 H1B . . 106.6 ?
C1 C2 O2 . . 123.6(9) ?
C1 C2 H2A . . 106.4 ?
O2 C2 H2A . . 106.4 ?
C1 C2 H2B . . 106.4 ?
O2 C2 H2B . . 106.4 ?
H2A C2 H2B . . 106.5 ?
C2' C1' O1 . . 126.8(8) ?
C2' C1' H1'1 . . 105.6 ?
O1 C1' H1'1 . . 105.6 ?
C2' C1' H1'2 . . 105.6 ?
O1 C1' H1'2 . . 105.6 ?
H1'1 C1' H1'2 . . 106.1 ?
C1' C2' O2 . . 119.3(8) ?
C1' C2' H2'1 . . 107.5 ?
O2 C2' H2'1 . . 107.5 ?
C1' C2' H2'2 . . 107.5 ?
O2 C2' H2'2 . . 107.5 ?
H2'1 C2' H2'2 . . 107.0 ?
O2 C3 C8 . . 117.66(18) ?
O2 C3 C4 . . 122.02(18) ?
C8 C3 C4 . . 120.32(18) ?
O1 C4 C3 . . 122.35(18) ?
O1 C4 C5 . . 118.11(18) ?
C3 C4 C5 . . 119.49(18) ?
C6 C5 O3 . . 125.25(18) ?
C6 C5 C4 . . 120.08(19) ?
O3 C5 C4 . . 114.67(17) ?
C5 C6 C7 . . 120.63(19) ?
C5 C6 H6A . . 119.7 ?
C7 C6 H6A . . 119.7 ?
C8 C7 C6 . . 119.15(18) ?
C8 C7 C16 . . 122.12(19) ?
C6 C7 C16 . . 118.73(19) ?
C3 C8 C7 . . 120.32(19) ?
C3 C8 H8A . . 119.8 ?
C7 C8 H8A . . 119.8 ?
O3 C9 C10 . . 109.76(17) ?
O3 C9 H9A . . 109.7 ?
C10 C9 H9A . . 109.7 ?
O3 C9 H9B . . 109.7 ?
C10 C9 H9B . . 109.7 ?
H9A C9 H9B . . 108.2 ?
C11 C10 C15 . . 118.2(2) ?
C11 C10 C9 . . 120.4(2) ?
C15 C10 C9 . . 121.4(2) ?
C10 C11 C12 . . 121.4(3) ?
C10 C11 H11A . . 119.3 ?
C12 C11 H11A . . 119.3 ?
C13 C12 C11 . . 119.9(2) ?
C13 C12 H12A . . 120.0 ?
C11 C12 H12A . . 120.0 ?
C12 C13 C14 . . 120.4(3) ?
C12 C13 H13A . . 119.8 ?
C14 C13 H13A . . 119.8 ?
C13 C14 C15 . . 119.8(3) ?
C13 C14 H14A . . 120.1 ?
C15 C14 H14A . . 120.1 ?
C10 C15 C14 . . 120.2(2) ?
C10 C15 H15A . . 119.9 ?
C14 C15 H15A . . 119.9 ?
C17 C16 C7 . . 126.4(2) ?
C17 C16 H16A . . 116.8 ?
C7 C16 H16A . . 116.8 ?
C16 C17 C18 . . 121.5(2) ?
C16 C17 H17A . . 119.2 ?
C18 C17 H17A . . 119.2 ?
O4 C18 C19 . . 119.96(18) ?
O4 C18 C17 . . 117.31(19) ?
C19 C18 C17 . . 122.70(18) ?
C20 C19 C24 . . 115.78(19) ?
C20 C19 C18 . . 126.62(18) ?
C24 C19 C18 . . 117.56(18) ?
O7 C20 C21 . . 122.18(19) ?
O7 C20 C19 . . 115.90(18) ?
C21 C20 C19 . . 121.86(19) ?
C20 C21 C22 . . 119.9(2) ?
C20 C21 H21A . . 120.0 ?
C22 C21 H21A . . 120.0 ?
O5 C22 C23 . . 123.9(2) ?
O5 C22 C21 . . 115.3(2) ?
C23 C22 C21 . . 120.8(2) ?
C22 C23 C24 . . 119.27(19) ?
C22 C23 H23A . . 120.4 ?
C24 C23 H23A . . 120.4 ?
O9 C24 C23 . . 116.51(18) ?
O9 C24 C19 . . 121.29(19) ?
C23 C24 C19 . . 122.19(19) ?
O6 C25 O5 . . 107.9(2) ?
O6 C25 H25A . . 110.1 ?
O5 C25 H25A . . 110.1 ?
O6 C25 H25B . . 110.1 ?
O5 C25 H25B . . 110.1 ?
H25A C25 H25B . . 108.4 ?
O6 C26 H26A . . 109.5 ?
O6 C26 H26B . . 109.5 ?
H26A C26 H26B . . 109.5 ?
O6 C26 H26C . . 109.5 ?
H26A C26 H26C . . 109.5 ?
H26B C26 H26C . . 109.5 ?
O8 C27 O7 . . 113.2(2) ?
O8 C27 H27A . . 108.9 ?
O7 C27 H27A . . 108.9 ?
O8 C27 H27B . . 108.9 ?
O7 C27 H27B . . 108.9 ?
H27A C27 H27B . . 107.8 ?
O8 C28 H28A . . 109.5 ?
O8 C28 H28B . . 109.5 ?
H28A C28 H28B . . 109.5 ?
O8 C28 H28C . . 109.5 ?
H28A C28 H28C . . 109.5 ?
H28B C28 H28C . . 109.5 ?
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
O1 C4 . 1.369(2) ?
O1 C1' . 1.413(10) ?
O1 C1 . 1.425(14) ?
O2 C3 . 1.366(2) ?
O2 C2' . 1.452(11) ?
O2 C2 . 1.458(10) ?
O3 C5 . 1.377(2) ?
O3 C9 . 1.416(3) ?
O4 C18 . 1.245(2) ?
O5 C22 . 1.352(3) ?
O5 C25 . 1.437(3) ?
O6 C25 . 1.362(3) ?
O6 C26 . 1.400(4) ?
O7 C20 . 1.370(2) ?
O7 C27 . 1.415(3) ?
O8 C27 . 1.341(3) ?
O8 C28 . 1.455(4) ?
O9 C24 . 1.340(2) ?
O9 H9C . 0.8200 ?
C1 C2 . 1.264(19) ?
C1 H1A . 0.9700 ?
C1 H1B . 0.9700 ?
C2 H2A . 0.9700 ?
C2 H2B . 0.9700 ?
C1' C2' . 1.282(15) ?
C1' H1'1 . 0.9700 ?
C1' H1'2 . 0.9700 ?
C2' H2'1 . 0.9700 ?
C2' H2'2 . 0.9700 ?
C3 C8 . 1.384(3) ?
C3 C4 . 1.388(3) ?
C4 C5 . 1.395(3) ?
C5 C6 . 1.374(3) ?
C6 C7 . 1.398(3) ?
C6 H6A . 0.9300 ?
C7 C8 . 1.388(3) ?
C7 C16 . 1.465(3) ?
C8 H8A . 0.9300 ?
C9 C10 . 1.497(3) ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C10 C11 . 1.358(3) ?
C10 C15 . 1.384(3) ?
C11 C12 . 1.385(3) ?
C11 H11A . 0.9300 ?
C12 C13 . 1.350(4) ?
C12 H12A . 0.9300 ?
C13 C14 . 1.357(4) ?
C13 H13A . 0.9300 ?
C14 C15 . 1.396(4) ?
C14 H14A . 0.9300 ?
C15 H15A . 0.9300 ?
C16 C17 . 1.319(3) ?
C16 H16A . 0.9300 ?
C17 C18 . 1.477(3) ?
C17 H17A . 0.9300 ?
C18 C19 . 1.464(3) ?
C19 C20 . 1.413(3) ?
C19 C24 . 1.422(3) ?
C20 C21 . 1.375(3) ?
C21 C22 . 1.387(3) ?
C21 H21A . 0.9300 ?
C22 C23 . 1.373(3) ?
C23 C24 . 1.384(3) ?
C23 H23A . 0.9300 ?
C25 H25A . 0.9700 ?
C25 H25B . 0.9700 ?
C26 H26A . 0.9600 ?
C26 H26B . 0.9600 ?
C26 H26C . 0.9600 ?
C27 H27A . 0.9700 ?
C27 H27B . 0.9700 ?
C28 H28A . 0.9600 ?
C28 H28B . 0.9600 ?
C28 H28C . 0.9600 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O9 H9C O4 . 0.82 1.71 2.448(2) 149
C6 H6A O9 2_676 0.93 2.57 3.426(3) 154
C21 H21A O8 2_486 0.93 2.53 3.453(3) 169
