#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/03/2200307.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_2200307
loop_
_publ_author_name
'Cai, Yue-Peng'
'Tan, Duan-Min'
'Su, Cheng-Yong'
'Liao, Miao-Fen'
'Kang, Bei-Sheng'
'Xu, Zun-Le'
_publ_section_title
7a,13b-Ethylenedioxy-1-hydroxy-7a,13b-dihydrodibenzo[a,kl]xanthene
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o528
_journal_page_last               o530
_journal_paper_doi               10.1107/S1600536801007772
_journal_volume                  57
_journal_year                    2001
_chemical_formula_iupac          'C22 H16 O4'
_chemical_formula_moiety         'C22 H16 O4'
_chemical_formula_sum            'C22 H16 O4'
_chemical_formula_weight         344.35
_chemical_name_systematic
;
7a,13b-ethylenedioxy-1-hydroxy-7a,13b-dihydrodibenzo[a,kl]xanthene
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 98.70(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.3170(10)
_cell_length_b                   17.787(4)
_cell_length_c                   12.422(2)
_cell_measurement_reflns_used    4616
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      30
_cell_measurement_theta_min      4.5
_cell_volume                     1598.1(5)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT+ (Bruker, 1999)'
_computing_molecular_graphics    'SHELXL (Bruker, 1998)'
_computing_publication_material  SHELXL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full .990
_diffrn_measured_fraction_theta_max .990
_diffrn_measurement_device_type  'Bruker Smart CCD'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .0191
_diffrn_reflns_av_sigmaI/netI    .0292
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11347
_diffrn_reflns_theta_full        30.01
_diffrn_reflns_theta_max         30.01
_diffrn_reflns_theta_min         4.44
_diffrn_standards_decay_%        none
_exptl_absorpt_coefficient_mu    .098
_exptl_absorpt_correction_T_max  .981
_exptl_absorpt_correction_T_min  .965
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   '(Blessing, 1995)'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          .36
_exptl_crystal_size_mid          .25
_exptl_crystal_size_min          .20
_refine_diff_density_max         .342
_refine_diff_density_min         -.222
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         4616
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          .0667
_refine_ls_R_factor_gt           .0452
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0825P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .1358
_reflns_number_gt                3271
_reflns_number_total             4616
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            na6063.cif
_cod_data_source_block           global
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2200307
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_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
_atom_site_type_symbol
O2 .56396(12) .29117(5) .65396(6) .0337(2) Uani d . 1 . . O
C9 .63783(16) .35741(7) .62057(10) .0318(3) Uani d . 1 . . C
C8 .61294(15) .37686(6) .50861(10) .0296(2) Uani d . 1 . . C
O1 .39572(15) .31130(6) .23628(8) .0469(3) Uani d . 1 . . O
C19 .56749(16) .18828(6) .45472(9) .0294(2) Uani d . 1 . . C
C7 .51217(15) .32901(6) .42884(9) .0289(2) Uani d . 1 . . C
C12 .36593(18) .18819(7) .63570(10) .0354(3) Uani d . 1 . . C
H12 .2842 .1859 .6861 .042 Uiso calc R 1 . . H
C3 .69376(17) .44490(7) .47881(12) .0376(3) Uani d . 1 . . C
C6 .48902(17) .35152(7) .32098(10) .0348(3) Uani d . 1 . . C
C10 .74099(18) .40058(8) .69820(12) .0435(3) Uani d . 1 . . C
H10 .7569 .3862 .7710 .052 Uiso calc R 1 . . H
C5 .56693(19) .41992(8) .29103(12) .0441(3) Uani d . 1 . . C
H5 .5495 .4344 .2183 .053 Uiso calc R 1 . . H
C14 .56702(18) .12583(7) .52425(10) .0355(3) Uani d . 1 . . C
C18 .67730(18) .18600(7) .37277(11) .0375(3) Uani d . 1 . . C
H18 .6759 .2265 .3253 .045 Uiso calc R 1 . . H
C13 .44621(19) .12611(7) .60829(10) .0392(3) Uani d . 1 . . C
H13 .4256 .0813 .6432 .047 Uiso calc R 1 . . H
C4 .66642(19) .46461(8) .36673(13) .0453(3) Uani d . 1 . . C
H4 .7176 .5089 .3449 .054 Uiso calc R 1 . . H
C17 .7892(2) .12445(8) .36032(12) .0470(3) Uani d . 1 . . C
H17 .8612 .1237 .3047 .056 Uiso calc R 1 . . H
C1 .8227(2) .46696(9) .66653(14) .0540(4) Uani d . 1 . . C
H1 .8946 .4961 .7189 .065 Uiso calc R 1 . . H
C15 .6809(2) .06489(8) .51185(12) .0470(3) Uani d . 1 . . C
H15 .6823 .0239 .5584 .056 Uiso calc R 1 . . H
C16 .7927(2) .06443(9) .43090(13) .0509(4) Uani d . 1 . . C
H16 .8699 .0237 .4243 .061 Uiso calc R 1 . . H
C2 .7984(2) .48920(8) .56065(15) .0501(4) Uani d . 1 . . C
H2 .8510 .5340 .5418 .060 Uiso calc R 1 . . H
O3 .26499(11) .23502(5) .40053(6) .0332(2) Uani d . 1 . . O
O4 .26225(12) .31544(5) .59398(7) .0362(2) Uani d . 1 . . O
C11 .40474(15) .26251(7) .58658(9) .0284(2) Uani d . 1 . . C
C22 .11804(17) .28724(8) .41166(11) .0389(3) Uani d . 1 . . C
H22A .0042 .2701 .3683 .047 Uiso calc R 1 . . H
H22B .1480 .3362 .3846 .047 Uiso calc R 1 . . H
C20 .43941(15) .25497(6) .46652(9) .0264(2) Uani d . 1 . . C
C21 .09101(17) .29390(8) .52858(11) .0421(3) Uani d . 1 . . C
H21A -.0031 .3313 .5354 .050 Uiso calc R 1 . . H
H21B .0498 .2461 .5539 .050 Uiso calc R 1 . . H
H1O .329(3) .2769(12) .2639(17) .086(7) Uiso d . 1 . . H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .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
C9 O2 C11 116.78(9)
C10 C9 O2 117.72(11)
C10 C9 C8 122.02(12)
O2 C9 C8 120.20(10)
C9 C8 C3 117.82(11)
C9 C8 C7 120.85(10)
C3 C8 C7 121.33(11)
C18 C19 C14 118.82(11)
C18 C19 C20 121.49(10)
C14 C19 C20 119.60(10)
C6 C7 C8 118.38(11)
C6 C7 C20 123.45(11)
C8 C7 C20 118.16(10)
C13 C12 C11 120.88(11)
C2 C3 C4 123.17(13)
C2 C3 C8 119.22(13)
C4 C3 C8 117.60(12)
O1 C6 C7 124.59(11)
O1 C6 C5 114.91(11)
C7 C6 C5 120.49(12)
C9 C10 C1 119.15(14)
C4 C5 C6 121.08(13)
C15 C14 C19 119.36(12)
C15 C14 C13 121.17(12)
C19 C14 C13 119.47(11)
C19 C18 C17 121.34(12)
C12 C13 C14 121.76(11)
C5 C4 C3 121.09(12)
C16 C17 C18 119.59(13)
C2 C1 C10 121.06(13)
C16 C15 C14 120.89(13)
C17 C16 C15 119.95(13)
C1 C2 C3 120.69(13)
C22 O3 C20 113.10(9)
C11 O4 C21 111.89(9)
O4 C11 O2 105.59(9)
O4 C11 C12 111.85(9)
O2 C11 C12 105.36(9)
O4 C11 C20 110.33(9)
O2 C11 C20 110.93(9)
C12 C11 C20 112.46(9)
O3 C22 C21 110.66(11)
O3 C20 C7 110.89(9)
O3 C20 C19 104.75(8)
C7 C20 C19 113.16(9)
O3 C20 C11 107.77(9)
C7 C20 C11 109.62(9)
C19 C20 C11 110.43(9)
O4 C21 C22 109.68(10)
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 C9 . 1.3858(14) ?
O2 C11 . 1.4222(14) ?
C9 C10 . 1.3671(17) ?
C9 C8 . 1.4179(17) ?
C8 C3 . 1.4205(16) ?
C8 C7 . 1.4244(17) ?
O1 C6 . 1.3666(17) ?
C19 C18 . 1.3896(17) ?
C19 C14 . 1.4073(17) ?
C19 C20 . 1.5325(16) ?
C7 C6 . 1.3840(17) ?
C7 C20 . 1.5206(16) ?
C12 C13 . 1.3195(19) ?
C12 C11 . 1.5009(17) ?
C3 C2 . 1.416(2) ?
C3 C4 . 1.420(2) ?
C6 C5 . 1.4170(18) ?
C10 C1 . 1.406(2) ?
C5 C4 . 1.356(2) ?
C14 C15 . 1.3899(19) ?
C14 C13 . 1.4665(18) ?
C18 C17 . 1.3896(19) ?
C17 C16 . 1.379(2) ?
C1 C2 . 1.359(2) ?
C15 C16 . 1.389(2) ?
O3 C22 . 1.4433(15) ?
O3 C20 . 1.4527(14) ?
O4 C11 . 1.4180(14) ?
O4 C21 . 1.4383(16) ?
C11 C20 . 1.5559(15) ?
C22 C21 . 1.4999(18) ?
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
O1 H1O O3 . .88(2) 1.97(2) 2.7404(14) 144.3(19)
O1 H1O O2 4_565 .88(2) 2.51(2) 3.0838(15) 123.3(17)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21132866
