#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/09/2230944.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_2230944
loop_
_publ_author_name
'Xiong, Hui-Ping'
'Wu, Zhi-Jun'
'Chen, Fa-Tang'
'Chen, Dong-Sheng'
_publ_section_title
;
 3-Hydroxy-1,2-dimethoxyxanthone
;
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1667
_journal_paper_doi               10.1107/S160053681102160X
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C15 H12 O5'
_chemical_formula_sum            'C15 H12 O5'
_chemical_formula_weight         272.25
_chemical_name_common            3-Hydroxy-1,2-dimethoxyxanthone
_chemical_name_systematic
;
3-Hydroxy-1,2-dimethoxy-9H-xanthen-9-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                94.634(4)
_cell_angle_beta                 93.561(4)
_cell_angle_gamma                115.027(4)
_cell_formula_units_Z            2
_cell_length_a                   7.338(2)
_cell_length_b                   7.824(3)
_cell_length_c                   11.964(4)
_cell_measurement_pressure       1
_cell_measurement_reflns_used    804
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.293
_cell_measurement_theta_min      2.893
_cell_volume                     616.8(4)
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1997)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_av_sigmaI/netI    0.0241
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            2562
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.72
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  0.9890
_exptl_absorpt_correction_T_min  0.9835
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             284
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.321
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2126
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0734
_refine_ls_R_factor_gt           0.0634
_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)+(0.1114P)²+0.1836P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1772
_refine_ls_wR_factor_ref         0.1895
_reflns_number_gt                1697
_reflns_number_total             2126
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            yk2009.cif
_cod_data_source_block           I
_cod_original_cell_volume        616.8(3)
_cod_database_code               2230944
_cod_database_fobs_code          2230944
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_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.2867(3) 0.6977(2) 0.52398(13) 0.0473(5) Uani d . 1 1 . .
O O2 0.2172(3) 0.1946(2) 0.35370(16) 0.0603(6) Uani d . 1 1 . .
O O3 0.2629(2) 0.3673(2) 0.15973(14) 0.0498(5) Uani d . 1 1 . .
O O4 0.2920(3) 0.6826(2) 0.06394(14) 0.0544(5) Uani d . 1 1 . .
O O5 0.3176(3) 0.9927(2) 0.19396(15) 0.0592(6) Uani d . 1 1 . .
H H5 0.2921 1.0654 0.2365 0.089 Uiso calc R 1 1 . .
C C1 0.2721(3) 0.5208(3) 0.22752(19) 0.0396(5) Uani d . 1 1 . .
C C2 0.2933(3) 0.6818(3) 0.17897(19) 0.0434(6) Uani d . 1 1 . .
C C3 0.3077(3) 0.8442(3) 0.2474(2) 0.0446(6) Uani d . 1 1 . .
C C4 0.3094(3) 0.8437(3) 0.3620(2) 0.0444(6) Uani d . 1 1 . .
H H4 0.3253 0.9520 0.4077 0.053 Uiso calc R 1 1 . .
C C5 0.2517(4) 0.5696(4) 0.6956(2) 0.0534(6) Uani d . 1 1 . .
H H5A 0.2708 0.6866 0.7317 0.064 Uiso calc R 1 1 . .
C C6 0.2189(4) 0.4191(4) 0.7557(2) 0.0599(7) Uani d . 1 1 . .
H H6 0.2148 0.4343 0.8333 0.072 Uiso calc R 1 1 . .
C C7 0.1919(4) 0.2451(4) 0.7025(2) 0.0599(7) Uani d . 1 1 . .
H H7 0.1689 0.1442 0.7444 0.072 Uiso calc R 1 1 . .
C C8 0.1988(4) 0.2210(4) 0.5886(2) 0.0522(6) Uani d . 1 1 . .
H H8 0.1827 0.1041 0.5537 0.063 Uiso calc R 1 1 . .
C C9 0.2376(3) 0.3482(3) 0.4018(2) 0.0417(6) Uani d . 1 1 . .
C C10 0.2654(3) 0.5149(3) 0.34488(19) 0.0376(5) Uani d . 1 1 . .
C C11 0.2873(3) 0.6818(3) 0.4091(2) 0.0397(5) Uani d . 1 1 . .
C C12 0.2559(3) 0.5436(3) 0.5796(2) 0.0437(6) Uani d . 1 1 . .
C C13 0.2302(3) 0.3713(3) 0.5240(2) 0.0422(6) Uani d . 1 1 . .
C C14 0.0691(5) 0.2530(4) 0.0989(3) 0.0700(8) Uani d . 1 1 . .
H H14A -0.0279 0.1977 0.1511 0.105 Uiso calc R 1 1 . .
H H14B 0.0770 0.1539 0.0496 0.105 Uiso calc R 1 1 . .
H H14C 0.0278 0.3306 0.0551 0.105 Uiso calc R 1 1 . .
C C15 0.4879(5) 0.7613(5) 0.0279(3) 0.0741(9) Uani d . 1 1 . .
H H15A 0.5620 0.8891 0.0637 0.111 Uiso calc R 1 1 . .
H H15B 0.4772 0.7615 -0.0524 0.111 Uiso calc R 1 1 . .
H H15C 0.5575 0.6865 0.0481 0.111 Uiso calc R 1 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
C12 O1 C11 . . 119.52(18) ?
C1 O3 C14 . . 114.41(19) ?
C2 O4 C15 . . 113.4(2) ?
C3 O5 H5 . . 109.5 ?
O3 C1 C2 . . 118.6(2) ?
O3 C1 C10 . . 120.1(2) ?
C2 C1 C10 . . 121.2(2) ?
O4 C2 C1 . . 120.4(2) ?
O4 C2 C3 . . 119.7(2) ?
C1 C2 C3 . . 119.8(2) ?
O5 C3 C4 . . 123.5(2) ?
O5 C3 C2 . . 116.7(2) ?
C4 C3 C2 . . 119.7(2) ?
C3 C4 C11 . . 119.7(2) ?
C3 C4 H4 . . 120.2 ?
C11 C4 H4 . . 120.2 ?
C6 C5 C12 . . 118.6(3) ?
C6 C5 H5A . . 120.7 ?
C12 C5 H5A . . 120.7 ?
C5 C6 C7 . . 120.9(3) ?
C5 C6 H6 . . 119.6 ?
C7 C6 H6 . . 119.6 ?
C8 C7 C6 . . 120.3(2) ?
C8 C7 H7 . . 119.9 ?
C6 C7 H7 . . 119.9 ?
C7 C8 C13 . . 120.5(3) ?
C7 C8 H8 . . 119.7 ?
C13 C8 H8 . . 119.7 ?
O2 C9 C10 . . 124.6(2) ?
O2 C9 C13 . . 120.0(2) ?
C10 C9 C13 . . 115.45(19) ?
C11 C10 C1 . . 116.5(2) ?
C11 C10 C9 . . 119.1(2) ?
C1 C10 C9 . . 124.3(2) ?
O1 C11 C4 . . 114.15(19) ?
O1 C11 C10 . . 123.0(2) ?
C4 C11 C10 . . 122.9(2) ?
O1 C12 C13 . . 122.1(2) ?
O1 C12 C5 . . 116.1(2) ?
C13 C12 C5 . . 121.8(2) ?
C12 C13 C8 . . 117.8(2) ?
C12 C13 C9 . . 120.7(2) ?
C8 C13 C9 . . 121.4(2) ?
O3 C14 H14A . . 109.5 ?
O3 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
O3 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
O4 C15 H15A . . 109.5 ?
O4 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
O4 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 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 C12 . 1.366(3) ?
O1 C11 . 1.370(3) ?
O2 C9 . 1.234(3) ?
O3 C1 . 1.368(3) ?
O3 C14 . 1.430(3) ?
O4 C2 . 1.376(3) ?
O4 C15 . 1.415(3) ?
O5 C3 . 1.349(3) ?
O5 H5 . 0.8200 ?
C1 C2 . 1.383(3) ?
C1 C10 . 1.412(3) ?
C2 C3 . 1.415(3) ?
C3 C4 . 1.370(3) ?
C4 C11 . 1.379(3) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.370(4) ?
C5 C12 . 1.391(4) ?
C5 H5A . 0.9300 ?
C6 C7 . 1.383(4) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.367(4) ?
C7 H7 . 0.9300 ?
C8 C13 . 1.405(3) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.463(3) ?
C9 C13 . 1.466(3) ?
C10 C11 . 1.402(3) ?
C12 C13 . 1.386(3) ?
C14 H14A . 0.9600 ?
C14 H14B . 0.9600 ?
C14 H14C . 0.9600 ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 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
O5 H5 O2 1_565 0.82 1.90 2.713(3) 169
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656813
