#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/86/2208641.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_2208641
loop_
_publ_author_name
'Suchada Chantrapromma'
'Sompong Boonsri'
'Hoong-Kun Fun'
'Shazia Anjum'
'Akkharawit Kanjana-opas'
_publ_section_title
2,3-Dihydro-7,8-dihydroxy-3-[(4-methoxyphenyl)methylene]-4H-1-benzopyran-4-one
_journal_coeditor_code           JH2004
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1254
_journal_page_last               o1256
_journal_paper_doi               10.1107/S1600536806007124
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C17 H14 O5'
_chemical_formula_moiety         'C17 H14 O5'
_chemical_formula_sum            'C17 H14 O5'
_chemical_formula_weight         298.28
_chemical_melting_point          .457E-305
_chemical_name_common            intricatinol
_chemical_name_systematic
2,3-dihydro-6,7-dihydroxy-3-[(4-methoxyphenyl)methylene]-4H-1-benzopyran-4-one
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 95.905(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.886(3)
_cell_length_b                   13.896(3)
_cell_length_c                   7.680(2)
_cell_measurement_reflns_used    2699
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      26.00
_cell_measurement_theta_min      1.59
_cell_volume                     1367.9(6)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material
;
SHELXTL and PLATON (Spek, 2003)
;
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Bruker, 1997)'
_diffrn_ambient_temperature      273(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type
;
Bruker SMART CCD area-detector
;
_diffrn_measurement_method       ω
_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  0.0192
_diffrn_reflns_av_sigmaI/netI    0.0192
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            7637
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.59
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  0.9889
_exptl_absorpt_correction_T_min  0.9471
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.185
_refine_ls_extinction_coef       0.0049(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         2687
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0490
_refine_ls_R_factor_gt           0.0419
_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)+(0.05P)²+0.3706P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1040
_refine_ls_wR_factor_ref         0.1096
_reflns_number_gt                2291
_reflns_number_total             2687
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jh2004.cif
_cod_data_source_block           I
_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_cell_volume        1367.9(5)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2208641
_cod_database_fobs_code          2208641
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
O O1 0.01132(9) 0.41003(8) 0.72392(16) 0.0505(3) Uani d . 1
O O2 0.09372(9) 0.12905(8) 0.82516(18) 0.0548(3) Uani d . 1
O O3 -0.31839(9) 0.31297(9) 0.45439(18) 0.0575(4) Uani d . 1
H H3A -0.3188 0.3694 0.4230 0.086 Uiso calc R 1
O O4 -0.18012(9) 0.45510(8) 0.54734(18) 0.0556(4) Uani d . 1
H H4A -0.1346 0.4922 0.5887 0.083 Uiso calc R 1
O O5 0.58076(9) 0.46678(9) 1.27173(18) 0.0597(4) Uani d . 1
C C1 -0.05713(11) 0.33709(11) 0.6815(2) 0.0377(4) Uani d . 1
C C2 -0.15188(11) 0.36279(11) 0.5908(2) 0.0401(4) Uani d . 1
C C3 -0.22361(11) 0.29103(12) 0.5394(2) 0.0425(4) Uani d . 1
C C4 -0.20130(12) 0.19485(12) 0.5757(2) 0.0456(4) Uani d . 1
H H4 -0.2497 0.1475 0.5394 0.055 Uiso calc R 1
C C5 -0.10820(12) 0.17036(11) 0.6646(2) 0.0443(4) Uani d . 1
H H5 -0.0937 0.1060 0.6896 0.053 Uiso calc R 1
C C6 -0.03415(11) 0.24051(11) 0.7189(2) 0.0382(4) Uani d . 1
C C7 0.06660(12) 0.21356(11) 0.8088(2) 0.0402(4) Uani d . 1
C C8 0.13531(11) 0.29399(10) 0.8767(2) 0.0388(4) Uani d . 1
C C9 0.09027(12) 0.39398(11) 0.8665(2) 0.0453(4) Uani d . 1
H H9A 0.0608 0.4076 0.9751 0.054 Uiso calc R 1
H H9B 0.1465 0.4394 0.8568 0.054 Uiso calc R 1
C C10 0.23154(12) 0.27122(11) 0.9468(2) 0.0401(4) Uani d . 1
H H10 0.2469 0.2060 0.9409 0.048 Uiso calc R 1
C C11 0.31678(11) 0.32909(11) 1.0305(2) 0.0378(3) Uani d . 1
C C12 0.41738(12) 0.29021(11) 1.0382(2) 0.0420(4) Uani d . 1
H H12 0.4265 0.2304 0.9876 0.050 Uiso calc R 1
C C13 0.50263(12) 0.33729(12) 1.1174(2) 0.0455(4) Uani d . 1
H H13 0.5685 0.3096 1.1204 0.055 Uiso calc R 1
C C14 0.49066(12) 0.42630(12) 1.1932(2) 0.0430(4) Uani d . 1
C C15 0.39257(13) 0.46712(12) 1.1891(2) 0.0464(4) Uani d . 1
H H15 0.3843 0.5271 1.2397 0.056 Uiso calc R 1
C C16 0.30687(12) 0.41842(12) 1.1095(2) 0.0445(4) Uani d . 1
H H16 0.2410 0.4459 1.1087 0.053 Uiso calc R 1
C C17 0.57693(16) 0.56264(13) 1.3341(3) 0.0618(5) Uani d . 1
H H17A 0.5491 0.6040 1.2406 0.093 Uiso calc R 1
H H17B 0.6460 0.5834 1.3762 0.093 Uiso calc R 1
H H17C 0.5330 0.5653 1.4277 0.093 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
_geom_angle_publ_flag
C1 O1 C9 117.30(12) y
C3 O3 H3A 109.5 ?
C2 O4 H4A 109.5 ?
C14 O5 C17 118.42(14) y
O1 C1 C2 116.31(13) ?
O1 C1 C6 123.19(13) ?
C2 C1 C6 120.45(14) ?
O4 C2 C1 124.24(13) ?
O4 C2 C3 116.88(14) ?
C1 C2 C3 118.87(14) ?
O3 C3 C2 120.95(15) ?
O3 C3 C4 118.00(14) ?
C2 C3 C4 121.05(14) ?
C5 C4 C3 119.65(14) ?
C5 C4 H4 120.2 ?
C3 C4 H4 120.2 ?
C4 C5 C6 120.99(15) ?
C4 C5 H5 119.5 ?
C6 C5 H5 119.5 ?
C5 C6 C1 118.99(14) ?
C5 C6 C7 120.70(14) ?
C1 C6 C7 120.29(13) ?
O2 C7 C6 121.69(14) ?
O2 C7 C8 122.02(14) ?
C6 C7 C8 116.29(13) ?
C10 C8 C7 117.21(14) ?
C10 C8 C9 125.16(14) ?
C7 C8 C9 117.60(13) ?
O1 C9 C8 115.04(13) ?
O1 C9 H9A 108.5 ?
C8 C9 H9A 108.5 ?
O1 C9 H9B 108.5 ?
C8 C9 H9B 108.5 ?
H9A C9 H9B 107.5 ?
C8 C10 C11 132.27(15) y
C8 C10 H10 113.9 ?
C11 C10 H10 113.9 ?
C16 C11 C12 116.84(14) ?
C16 C11 C10 125.84(14) ?
C12 C11 C10 117.28(14) ?
C13 C12 C11 122.16(15) ?
C13 C12 H12 118.9 ?
C11 C12 H12 118.9 ?
C12 C13 C14 119.77(15) ?
C12 C13 H13 120.1 ?
C14 C13 H13 120.1 ?
O5 C14 C13 115.19(14) ?
O5 C14 C15 124.88(16) ?
C13 C14 C15 119.92(15) ?
C14 C15 C16 119.72(16) ?
C14 C15 H15 120.1 ?
C16 C15 H15 120.1 ?
C15 C16 C11 121.59(15) ?
C15 C16 H16 119.2 ?
C11 C16 H16 119.2 ?
O5 C17 H17A 109.5 ?
O5 C17 H17B 109.5 ?
H17A C17 H17B 109.5 ?
O5 C17 H17C 109.5 ?
H17A C17 H17C 109.5 ?
H17B C17 H17C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 1.3610(18) y
O1 C9 1.4332(19) y
O2 C7 1.2280(18) y
O3 C3 1.3589(18) y
O3 H3A 0.8200 ?
O4 C2 1.3654(18) y
O4 H4A 0.8200 ?
O5 C14 1.3725(19) y
O5 C17 1.418(2) ?
C1 C2 1.388(2) ?
C1 C6 1.398(2) ?
C2 C3 1.389(2) ?
C3 C4 1.389(2) ?
C4 C5 1.361(2) ?
C4 H4 0.9300 ?
C5 C6 1.397(2) ?
C5 H5 0.9300 ?
C6 C7 1.455(2) ?
C7 C8 1.487(2) ?
C8 C10 1.338(2) y
C8 C9 1.505(2) ?
C9 H9A 0.9700 ?
C9 H9B 0.9700 ?
C10 C11 1.457(2) ?
C10 H10 0.9300 ?
C11 C16 1.393(2) ?
C11 C12 1.400(2) ?
C12 C13 1.367(2) ?
C12 H12 0.9300 ?
C13 C14 1.382(2) ?
C13 H13 0.9300 ?
C14 C15 1.383(2) ?
C15 C16 1.383(2) ?
C15 H15 0.9300 ?
C16 H16 0.9300 ?
C17 H17A 0.9600 ?
C17 H17B 0.9600 ?
C17 H17C 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
_geom_hbond_publ_flag
O3 H3A O4 1_555 0.82 2.2743 2.706(2) 113 y
O3 H3A O5 1_454 0.82 2.1323 2.802(2) 138 y
O4 H4A O1 1_555 0.82 2.3486 2.762(2) 112 y
O4 H4A O2 2_556 0.82 2.0639 2.796(2) 148 y
C10 H10 O2 1_555 0.93 2.3385 2.755(2) 107 y
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_publ_flag
C9 O1 C1 C2 157.92(15) ?
C9 O1 C1 C6 -24.6(2) ?
O1 C1 C2 O4 -1.7(2) ?
C6 C1 C2 O4 -179.29(15) ?
O1 C1 C2 C3 178.10(14) ?
C6 C1 C2 C3 0.5(2) ?
O4 C2 C3 O3 -1.9(2) ?
C1 C2 C3 O3 178.31(15) ?
O4 C2 C3 C4 179.13(15) ?
C1 C2 C3 C4 -0.7(3) ?
O3 C3 C4 C5 -178.34(15) ?
C2 C3 C4 C5 0.7(3) ?
C3 C4 C5 C6 -0.5(3) ?
C4 C5 C6 C1 0.4(2) ?
C4 C5 C6 C7 -177.95(15) ?
O1 C1 C6 C5 -177.76(15) ?
C2 C1 C6 C5 -0.4(2) ?
O1 C1 C6 C7 0.6(2) ?
C2 C1 C6 C7 177.96(14) ?
C5 C6 C7 O2 7.0(2) ?
C1 C6 C7 O2 -171.29(15) ?
C5 C6 C7 C8 -174.05(15) ?
C1 C6 C7 C8 7.7(2) ?
O2 C7 C8 C10 4.4(2) ?
C6 C7 C8 C10 -174.58(14) ?
O2 C7 C8 C9 -173.75(16) ?
C6 C7 C8 C9 7.3(2) ?
C1 O1 C9 C8 38.2(2) ?
C10 C8 C9 O1 152.33(16) ?
C7 C8 C9 O1 -29.7(2) ?
C7 C8 C10 C11 -177.21(15) y
C9 C8 C10 C11 0.7(3) ?
C8 C10 C11 C16 23.0(3) ?
C8 C10 C11 C12 -159.41(17) ?
C16 C11 C12 C13 -0.6(2) ?
C10 C11 C12 C13 -178.40(15) ?
C11 C12 C13 C14 0.0(3) ?
C17 O5 C14 C13 172.68(15) y
C17 O5 C14 C15 -8.6(2) y
C12 C13 C14 O5 179.01(14) ?
C12 C13 C14 C15 0.2(3) ?
O5 C14 C15 C16 -178.46(15) ?
C13 C14 C15 C16 0.2(3) ?
C14 C15 C16 C11 -0.9(3) ?
C12 C11 C16 C15 1.1(2) ?
C10 C11 C16 C15 178.62(15) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 28289794
