#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/90/2209008.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_2209008
loop_
_publ_author_name
'Suchada Chantrapromma'
'Hoong-Kun Fun'
'Sorwaporn Koysomboon'
'Kan Chantrapromma'
_publ_section_title
;
 4-Methoxy-7-phenyl-6,7-dihydrofuro[3,2-g]chromen-5-one
;
_journal_coeditor_code           SJ2045
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1984
_journal_page_last               o1986
_journal_paper_doi               10.1107/S1600536806013900
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C18 H12 O4'
_chemical_formula_moiety         'C18 H12 O4'
_chemical_formula_sum            'C18 H12 O4'
_chemical_formula_weight         292.28
_chemical_melting_point          .454E-305
_chemical_name_common
;
pinnatin
;
_chemical_name_systematic
;
4-Methoxy-7-phenyl-6,7-dihydrofuro[3,2-g]chromen-5-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           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.9450(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.61740(10)
_cell_length_b                   15.5622(3)
_cell_length_c                   9.86340(10)
_cell_measurement_reflns_used    3821
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      30.00
_cell_measurement_theta_min      2.38
_cell_volume                     1313.03(3)
_computing_cell_refinement       APEX2
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  'SHELXTL and PLATON (Spek, 2003)'
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1998)'
_diffrn_ambient_temperature      297(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART APEX2 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  0.0793
_diffrn_reflns_av_sigmaI/netI    0.0426
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            32598
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         2.38
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  0.9896
_exptl_absorpt_correction_T_min  0.9603
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.479
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Slab
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.355
_refine_diff_density_min         -0.286
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3821
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0745
_refine_ls_R_factor_gt           0.0536
_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)+(0.0381P)²+1.1211P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1112
_refine_ls_wR_factor_ref         0.1217
_reflns_number_gt                2950
_reflns_number_total             3821
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj2045.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_sg_symbol_H-M      'P 21/c'
_cod_database_code               2209008
_cod_database_fobs_code          2209008
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 0.66963(13) 0.03164(7) 0.76180(11) 0.0164(2) Uani d . 1
O O2 0.80177(13) -0.06643(7) 1.21530(11) 0.0183(2) Uani d . 1
O O3 0.99746(14) -0.12086(8) 0.61528(11) 0.0206(3) Uani d . 1
O O4 1.08645(13) -0.16978(7) 0.86943(11) 0.0197(3) Uani d . 1
C C1 0.69640(17) 0.03455(10) 0.62847(15) 0.0147(3) Uani d . 1
C C2 0.80709(18) -0.01361(10) 0.58135(16) 0.0162(3) Uani d . 1
H H2A 0.8228 -0.0081 0.4901 0.019 Uiso calc R 1
C C3 0.90383(17) -0.07415(10) 0.66650(15) 0.0150(3) Uani d . 1
C C4 0.87855(17) -0.07417(10) 0.81126(15) 0.0146(3) Uani d . 1
C C5 0.96894(18) -0.12430(10) 0.91289(15) 0.0148(3) Uani d . 1
C C6 0.93396(18) -0.12146(10) 1.04806(15) 0.0153(3) Uani d . 1
C C7 0.99202(19) -0.16098(10) 1.17853(16) 0.0177(3) Uani d . 1
H H7A 1.0699 -0.2025 1.1936 0.021 Uiso calc R 1
C C8 0.91146(19) -0.12588(10) 1.27211(16) 0.0190(3) Uani d . 1
H H8A 0.9270 -0.1396 1.3645 0.023 Uiso calc R 1
C C9 0.81554(18) -0.06491(10) 1.07873(15) 0.0156(3) Uani d . 1
C C10 0.72532(18) -0.01399(10) 0.98554(16) 0.0169(3) Uani d . 1
H H10A 0.6471 0.0219 1.0103 0.020 Uiso calc R 1
C C11 0.75999(18) -0.02033(10) 0.85229(15) 0.0149(3) Uani d . 1
C C12 0.59180(17) 0.09619(10) 0.54784(15) 0.0151(3) Uani d . 1
C C13 0.48043(18) 0.14288(10) 0.60917(16) 0.0173(3) Uani d . 1
H H13A 0.4706 0.1347 0.7011 0.021 Uiso calc R 1
C C14 0.38404(19) 0.20177(10) 0.53269(17) 0.0186(3) Uani d . 1
H H14A 0.3107 0.2330 0.5740 0.022 Uiso calc R 1
C C15 0.39726(19) 0.21389(10) 0.39520(17) 0.0198(3) Uani d . 1
H H15A 0.3327 0.2530 0.3443 0.024 Uiso calc R 1
C C16 0.5072(2) 0.16734(11) 0.33385(16) 0.0203(3) Uani d . 1
H H16A 0.5157 0.1754 0.2416 0.024 Uiso calc R 1
C C17 0.60441(19) 0.10896(10) 0.40886(16) 0.0181(3) Uani d . 1
H H17A 0.6780 0.0783 0.3669 0.022 Uiso calc R 1
C C18 1.19085(19) -0.21691(11) 0.96639(17) 0.0204(3) Uani d . 1
H H18C 1.2676 -0.2457 0.9199 0.031 Uiso calc R 1
H H18A 1.1327 -0.2586 1.0113 0.031 Uiso calc R 1
H H18B 1.2421 -0.1780 1.0329 0.031 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 C11 119.83(12) ?
C9 O2 C8 105.83(12) ?
C5 O4 C18 119.46(12) y
C2 C1 O1 121.79(14) ?
C2 C1 C12 126.08(14) y
O1 C1 C12 112.13(13) ?
C1 C2 C3 122.96(14) ?
C1 C2 H2A 118.5 ?
C3 C2 H2A 118.5 ?
O3 C3 C2 120.04(14) ?
O3 C3 C4 125.21(14) ?
C2 C3 C4 114.75(13) ?
C11 C4 C5 118.31(13) ?
C11 C4 C3 118.27(13) ?
C5 C4 C3 123.41(14) ?
O4 C5 C6 125.11(14) ?
O4 C5 C4 115.57(13) ?
C6 C5 C4 119.29(14) ?
C5 C6 C9 117.95(14) ?
C5 C6 C7 137.29(15) ?
C9 C6 C7 104.72(13) ?
C8 C7 C6 106.58(14) ?
C8 C7 H7A 126.7 ?
C6 C7 H7A 126.7 ?
C7 C8 O2 112.20(13) ?
C7 C8 H8A 123.9 ?
O2 C8 H8A 123.9 ?
O2 C9 C10 123.87(14) ?
O2 C9 C6 110.65(13) ?
C10 C9 C6 125.48(14) ?
C9 C10 C11 114.96(14) ?
C9 C10 H10A 122.5 ?
C11 C10 H10A 122.5 ?
O1 C11 C10 113.81(13) ?
O1 C11 C4 122.25(13) ?
C10 C11 C4 123.93(14) ?
C13 C12 C17 119.19(14) ?
C13 C12 C1 120.62(14) ?
C17 C12 C1 120.19(14) ?
C14 C13 C12 120.14(14) ?
C14 C13 H13A 119.9 ?
C12 C13 H13A 119.9 ?
C15 C14 C13 120.25(15) ?
C15 C14 H14A 119.9 ?
C13 C14 H14A 119.9 ?
C14 C15 C16 119.75(15) ?
C14 C15 H15A 120.1 ?
C16 C15 H15A 120.1 ?
C17 C16 C15 120.62(15) ?
C17 C16 H16A 119.7 ?
C15 C16 H16A 119.7 ?
C16 C17 C12 120.05(15) ?
C16 C17 H17A 120.0 ?
C12 C17 H17A 120.0 ?
O4 C18 H18C 109.5 ?
O4 C18 H18A 109.5 ?
H18C C18 H18A 109.5 ?
O4 C18 H18B 109.5 ?
H18C C18 H18B 109.5 ?
H18A C18 H18B 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 1.3631(18) y
O1 C11 1.3744(18) y
O2 C9 1.3667(18) y
O2 C8 1.3912(19) y
O3 C3 1.2382(19) y
O4 C5 1.3473(18) y
O4 C18 1.4331(18) y
C1 C2 1.340(2) ?
C1 C12 1.480(2) ?
C2 C3 1.456(2) ?
C2 H2A 0.9300 ?
C3 C4 1.470(2) ?
C4 C11 1.418(2) ?
C4 C5 1.425(2) ?
C5 C6 1.403(2) ?
C6 C9 1.408(2) ?
C6 C7 1.459(2) ?
C7 C8 1.337(2) y
C7 H7A 0.9300 ?
C8 H8A 0.9300 ?
C9 C10 1.380(2) ?
C10 C11 1.386(2) ?
C10 H10A 0.9300 ?
C12 C13 1.398(2) ?
C12 C17 1.402(2) ?
C13 C14 1.396(2) ?
C13 H13A 0.9300 ?
C14 C15 1.387(2) ?
C14 H14A 0.9300 ?
C15 C16 1.388(2) ?
C15 H15A 0.9300 ?
C16 C17 1.387(2) ?
C16 H16A 0.9300 ?
C17 H17A 0.9300 ?
C18 H18C 0.9600 ?
C18 H18A 0.9600 ?
C18 H18B 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
C8 H8A O3 1_556 0.93 2.4918 3.3772(19) 159 yes
C13 H13A O1 1_555 0.93 2.3715 2.7070(19) 101 yes
C18 H18A O3 4_556 0.96 2.4936 3.450(2) 174 yes
C18 H18C Cg1 2_746 0.96 2.6857 3.3621(18) 128 yes
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
C11 O1 C1 C2 1.5(2) ?
C11 O1 C1 C12 -177.92(12) ?
O1 C1 C2 C3 1.8(2) ?
C12 C1 C2 C3 -178.85(14) ?
C1 C2 C3 O3 175.41(15) y
C1 C2 C3 C4 -4.1(2) ?
O3 C3 C4 C11 -176.22(15) y
C2 C3 C4 C11 3.3(2) ?
O3 C3 C4 C5 5.0(2) ?
C2 C3 C4 C5 -175.51(14) ?
C18 O4 C5 C6 -2.9(2) y
C18 O4 C5 C4 175.31(13) y
C11 C4 C5 O4 -175.78(13) ?
C3 C4 C5 O4 3.0(2) ?
C11 C4 C5 C6 2.5(2) ?
C3 C4 C5 C6 -178.67(14) ?
O4 C5 C6 C9 174.62(14) ?
C4 C5 C6 C9 -3.5(2) ?
O4 C5 C6 C7 -2.7(3) ?
C4 C5 C6 C7 179.22(17) ?
C5 C6 C7 C8 176.22(18) ?
C9 C6 C7 C8 -1.29(17) ?
C6 C7 C8 O2 0.79(18) ?
C9 O2 C8 C7 0.06(18) ?
C8 O2 C9 C10 179.50(15) ?
C8 O2 C9 C6 -0.93(17) ?
C5 C6 C9 O2 -176.71(13) ?
C7 C6 C9 O2 1.37(17) ?
C5 C6 C9 C10 2.8(2) ?
C7 C6 C9 C10 -179.07(15) ?
O2 C9 C10 C11 178.54(14) ?
C6 C9 C10 C11 -1.0(2) ?
C1 O1 C11 C10 177.04(13) ?
C1 O1 C11 C4 -2.2(2) ?
C9 C10 C11 O1 -179.38(13) ?
C9 C10 C11 C4 -0.2(2) ?
C5 C4 C11 O1 178.50(13) ?
C3 C4 C11 O1 -0.4(2) ?
C5 C4 C11 C10 -0.6(2) ?
C3 C4 C11 C10 -179.51(14) ?
C2 C1 C12 C13 -179.98(15) y
O1 C1 C12 C13 -0.6(2) ?
C2 C1 C12 C17 -0.5(2) ?
O1 C1 C12 C17 178.85(13) ?
C17 C12 C13 C14 -0.4(2) ?
C1 C12 C13 C14 179.03(14) ?
C12 C13 C14 C15 0.5(2) ?
C13 C14 C15 C16 -0.2(2) ?
C14 C15 C16 C17 -0.2(2) ?
C15 C16 C17 C12 0.3(2) ?
C13 C12 C17 C16 0.0(2) ?
C1 C12 C17 C16 -179.42(14) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 4478650
