#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:43:10 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301803 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/16/2201607.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_2201607
loop_
_publ_author_name
'Liu, Yen-Hsiang'
'Robbs, Steven L.'
'Fronczek, Frank R. '
'Watkins, Steven F.'
'Fischer, Nikolaus H. '
_publ_section_title
;
 A new polymorph of atranorin, a lichen paradepside
;
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o877
_journal_page_last               o878
_journal_paper_doi               10.1107/S1600536802011856
_journal_volume                  58
_journal_year                    2002
_chemical_formula_iupac          'C19 H18 O8'
_chemical_formula_moiety         'C19 H18 O8'
_chemical_formula_sum            'C19 H18 O8'
_chemical_formula_weight         374.33
_chemical_name_common            atranorin
_chemical_name_systematic
;
Methyl 4-(3-formyl-2,4-dihydroxy-6-methyl-benzoyloxy)-2-hydroxy-
3,6-dimethyl-benzoate
;
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 109.745(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.929(3)
_cell_length_b                   10.976(3)
_cell_length_c                   14.843(3)
_cell_measurement_reflns_used    5466
_cell_measurement_temperature    120
_cell_measurement_theta_max      32.0
_cell_measurement_theta_min      2.5
_cell_volume                     1675.8(7)
_computing_cell_refinement       'HKL SCALEPACK (Otwinowski & Minor 1997)'
_computing_data_collection       'COLLECT (Nonius, 1999)'
_computing_data_reduction
'HKL DENZO (Otwinowski & Minor, 1997) and SCALEPACK'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      120
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device
'KappaCCD (with an Oxford Cryosystems Cryostream cooler)'
_diffrn_measurement_method       'ω scans with κ offsets'
_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  0.025
_diffrn_reflns_av_sigmaI/netI    0.0410
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            21781
_diffrn_reflns_theta_full        32.0
_diffrn_reflns_theta_max         32.0
_diffrn_reflns_theta_min         2.7
_diffrn_standards_decay_%        <2
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.43
_refine_diff_density_min         -0.29
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     260
_refine_ls_number_reflns         5796
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.080
_refine_ls_R_factor_gt           0.050
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0551P)²+0.7055P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1162
_refine_ls_wR_factor_ref         0.1366
_reflns_number_gt                4257
_reflns_number_total             5796
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            om6098.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        1675.7(7)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2201607
_cod_database_fobs_code          2201607
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
O1 0.00936(9) 0.22817(10) 0.12734(7) 0.0280(2) Uani d . 1 . . O
O2 0.28830(10) 0.07016(9) 0.03346(7) 0.0248(2) Uani d . 1 . . O
H2O 0.2043(19) 0.0886(17) 0.0052(14) 0.037 Uiso d . 1 . . H
O3 0.05911(10) 0.15003(10) 0.00532(7) 0.0294(2) Uani d . 1 . . O
O4 0.61784(8) 0.15025(9) 0.32857(6) 0.0216(2) Uani d . 1 . . O
O5 0.56142(9) 0.04303(10) 0.43694(7) 0.0277(2) Uani d . 1 . . O
O6 1.16021(9) 0.12662(10) 0.66952(7) 0.0274(2) Uani d . 1 . . O
H6O 1.1607(19) 0.0925(18) 0.7251(15) 0.041 Uiso d . 1 . . H
O7 0.72501(9) 0.00250(9) 0.60260(7) 0.0240(2) Uani d . 1 . . O
H7O 0.6519(19) 0.0059(17) 0.5546(14) 0.036 Uiso d . 1 . . H
O8 1.08114(10) 0.02204(10) 0.79484(7) 0.0299(2) Uani d . 1 . . O
C1 0.48601(11) 0.15799(12) 0.26991(8) 0.0182(2) Uani d . 1 . . C
C2 0.40202(12) 0.22551(12) 0.30214(8) 0.0199(2) Uani d . 1 . . C
H2 0.4331 0.2625 0.3636 0.024 Uiso calc R 1 . . H
C3 0.27324(12) 0.23953(12) 0.24560(8) 0.0186(2) Uani d . 1 . . C
C4 0.23023(11) 0.18357(11) 0.15373(8) 0.0177(2) Uani d . 1 . . C
C5 0.32103(12) 0.12114(11) 0.12148(8) 0.0185(2) Uani d . 1 . . C
C6 0.45190(12) 0.10629(11) 0.18017(9) 0.0189(2) Uani d . 1 . . C
C7 0.54606(14) 0.03773(14) 0.14543(11) 0.0289(3) Uani d . 1 . . C
H7A 0.5891 0.0945 0.1148 0.043 Uiso calc R 1 . . H
H7B 0.4992 -0.0242 0.0990 0.043 Uiso calc R 1 . . H
H7C 0.6114 -0.0019 0.1998 0.043 Uiso calc R 1 . . H
C8 0.18933(13) 0.31664(14) 0.28570(10) 0.0275(3) Uani d . 1 . . C
H8A 0.1257 0.2647 0.3005 0.041 Uiso calc R 1 . . H
H8B 0.1437 0.3781 0.2384 0.041 Uiso calc R 1 . . H
H8C 0.2441 0.3572 0.3443 0.041 Uiso calc R 1 . . H
C9 0.09397(12) 0.18620(12) 0.08857(9) 0.0203(2) Uani d . 1 . . C
C10 -0.12623(13) 0.22889(16) 0.06652(11) 0.0325(3) Uani d . 1 . . C
H10A -0.1369 0.2810 0.0107 0.049 Uiso calc R 1 . . H
H10B -0.1797 0.2605 0.1027 0.049 Uiso calc R 1 . . H
H10C -0.1537 0.1457 0.0451 0.049 Uiso calc R 1 . . H
C11 0.64570(12) 0.09578(11) 0.41488(9) 0.0186(2) Uani d . 1 . . C
C12 0.78207(11) 0.10492(11) 0.47735(8) 0.0163(2) Uani d . 1 . . C
C13 0.81263(12) 0.05667(11) 0.57094(8) 0.0172(2) Uani d . 1 . . C
C14 0.94016(12) 0.06362(11) 0.63768(9) 0.0185(2) Uani d . 1 . . C
C15 1.03717(12) 0.11816(12) 0.60878(9) 0.0197(2) Uani d . 1 . . C
C16 1.00832(12) 0.16495(12) 0.51672(9) 0.0199(2) Uani d . 1 . . C
H16 1.0755 0.2010 0.4986 0.024 Uiso calc R 1 . . H
C17 0.88335(12) 0.15983(11) 0.45121(9) 0.0181(2) Uani d . 1 . . C
C18 0.86281(13) 0.21517(14) 0.35434(9) 0.0256(3) Uani d . 1 . . C
H18A 0.9466 0.2417 0.3506 0.038 Uiso calc R 1 . . H
H18B 0.8045 0.2855 0.3449 0.038 Uiso calc R 1 . . H
H18C 0.8240 0.1544 0.3045 0.038 Uiso calc R 1 . . H
C19 0.97066(13) 0.01870(13) 0.73465(9) 0.0237(3) Uani d . 1 . . C
H19 0.9011(17) -0.0163(16) 0.7525(12) 0.028 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 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
C9 O1 C10 116.55(11)
C5 O2 H2O 104.7(12)
C11 O4 C1 117.86(9)
C15 O6 H6O 106.2(13)
C13 O7 H7O 105.0(13)
C6 C1 C2 124.04(11)
C6 C1 O4 117.24(11)
C2 C1 O4 118.46(11)
C3 C2 C1 120.51(11)
C3 C2 H2 119.7
C1 C2 H2 119.7
C2 C3 C4 118.21(11)
C2 C3 C8 116.90(11)
C4 C3 C8 124.87(11)
C5 C4 C3 119.39(11)
C5 C4 C9 117.05(11)
C3 C4 C9 123.56(11)
O2 C5 C6 115.51(11)
O2 C5 C4 122.66(11)
C6 C5 C4 121.83(11)
C1 C6 C5 115.86(11)
C1 C6 C7 123.08(11)
C5 C6 C7 121.06(11)
C6 C7 H7A 109.5
C6 C7 H7B 109.5
H7A C7 H7B 109.5
C6 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
C3 C8 H8A 109.5
C3 C8 H8B 109.5
H8A C8 H8B 109.5
C3 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
O3 C9 O1 121.58(12)
O3 C9 C4 123.61(12)
O1 C9 C4 114.79(11)
O1 C10 H10A 109.5
O1 C10 H10B 109.5
H10A C10 H10B 109.5
O1 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
O5 C11 O4 120.96(11)
O5 C11 C12 123.98(11)
O4 C11 C12 115.06(10)
C13 C12 C17 118.53(11)
C13 C12 C11 116.49(10)
C17 C12 C11 124.97(11)
O7 C13 C14 115.50(10)
O7 C13 C12 123.37(11)
C14 C13 C12 121.13(11)
C15 C14 C13 118.44(11)
C15 C14 C19 120.26(11)
C13 C14 C19 121.28(11)
O6 C15 C16 118.41(11)
O6 C15 C14 120.74(11)
C16 C15 C14 120.85(11)
C17 C16 C15 121.12(11)
C17 C16 H16 119.4
C15 C16 H16 119.4
C16 C17 C12 119.93(11)
C16 C17 C18 116.59(11)
C12 C17 C18 123.48(11)
C17 C18 H18A 109.5
C17 C18 H18B 109.5
H18A C18 H18B 109.5
C17 C18 H18C 109.5
H18A C18 H18C 109.5
H18B C18 H18C 109.5
O8 C19 C14 123.25(13)
O8 C19 H19 118.7(10)
C14 C19 H19 118.0(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
O1 C9 . 1.3260(16) ?
O1 C10 . 1.4515(16) ?
O2 C5 . 1.3536(15) ?
O2 H2O . 0.89(2) ?
O3 C9 . 1.2294(16) ?
O4 C11 . 1.3520(15) ?
O4 C1 . 1.4119(14) ?
O5 C11 . 1.2225(15) ?
O6 C15 . 1.3456(15) ?
O6 H6O . 0.90(2) ?
O7 C13 . 1.3398(15) ?
O7 H7O . 0.87(2) ?
O8 C19 . 1.2363(16) ?
C1 C6 . 1.3783(17) ?
C1 C2 . 1.3847(18) ?
C2 C3 . 1.3823(17) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.4230(17) ?
C3 C8 . 1.5099(18) ?
C4 C5 . 1.4158(17) ?
C4 C9 . 1.4767(16) ?
C5 C6 . 1.4104(17) ?
C6 C7 . 1.4998(18) ?
C7 H7A . 0.9800 ?
C7 H7B . 0.9800 ?
C7 H7C . 0.9800 ?
C8 H8A . 0.9800 ?
C8 H8B . 0.9800 ?
C8 H8C . 0.9800 ?
C10 H10A . 0.9800 ?
C10 H10B . 0.9800 ?
C10 H10C . 0.9800 ?
C11 C12 . 1.4688(16) ?
C12 C13 . 1.4172(16) ?
C12 C17 . 1.4244(17) ?
C13 C14 . 1.4131(17) ?
C14 C15 . 1.4050(18) ?
C14 C19 . 1.4497(17) ?
C15 C16 . 1.3926(18) ?
C16 C17 . 1.3844(17) ?
C16 H16 . 0.9500 ?
C17 C18 . 1.5063(17) ?
C18 H18A . 0.9800 ?
C18 H18B . 0.9800 ?
C18 H18C . 0.9800 ?
C19 H19 . 0.966(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
O2 H2O O3 . 0.89(2) 1.72(2) 2.5515(14) 152.5(18)
O6 H6O O8 . 0.90(2) 1.74(2) 2.5711(15) 151.1(18)
O7 H7O O5 . 0.87(2) 1.74(2) 2.5437(13) 151.9(18)
O7 H7O O5 3_656 0.87(2) 2.437(19) 3.0251(14) 125.1(16)
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 O4 C1 C6 -122.35(13) ?
C11 O4 C1 C2 63.23(15) yes
C6 C1 C2 C3 3.5(2) ?
O4 C1 C2 C3 177.52(11) ?
C1 C2 C3 C4 -0.42(18) ?
C1 C2 C3 C8 -178.85(12) ?
C2 C3 C4 C5 -3.11(18) ?
C8 C3 C4 C5 175.18(12) ?
C2 C3 C4 C9 176.71(12) ?
C8 C3 C4 C9 -5.0(2) ?
C3 C4 C5 O2 -177.17(11) ?
C9 C4 C5 O2 3.00(18) ?
C3 C4 C5 C6 3.92(18) ?
C9 C4 C5 C6 -175.91(11) ?
C2 C1 C6 C5 -2.70(18) ?
O4 C1 C6 C5 -176.78(11) ?
C2 C1 C6 C7 177.47(13) ?
O4 C1 C6 C7 3.39(18) ?
O2 C5 C6 C1 179.97(11) ?
C4 C5 C6 C1 -1.05(18) ?
O2 C5 C6 C7 -0.19(18) ?
C4 C5 C6 C7 178.79(12) ?
C10 O1 C9 O3 0.13(19) ?
C10 O1 C9 C4 -178.22(12) ?
C5 C4 C9 O3 -8.62(19) ?
C3 C4 C9 O3 171.55(13) ?
C5 C4 C9 O1 169.70(11) ?
C3 C4 C9 O1 -10.13(18) yes
C1 O4 C11 O5 8.02(18) ?
C1 O4 C11 C12 -172.30(11) yes
O5 C11 C12 C13 -4.84(19) yes
O4 C11 C12 C13 175.49(11) ?
O5 C11 C12 C17 176.26(13) ?
O4 C11 C12 C17 -3.41(18) ?
C17 C12 C13 O7 -179.56(11) ?
C11 C12 C13 O7 1.46(18) ?
C17 C12 C13 C14 0.67(18) ?
C11 C12 C13 C14 -178.30(11) ?
O7 C13 C14 C15 179.32(11) ?
C12 C13 C14 C15 -0.90(18) ?
O7 C13 C14 C19 -2.26(18) ?
C12 C13 C14 C19 177.52(12) ?
C13 C14 C15 O6 -179.76(11) ?
C19 C14 C15 O6 1.80(19) ?
C13 C14 C15 C16 0.37(18) ?
C19 C14 C15 C16 -178.07(12) ?
O6 C15 C16 C17 -179.49(12) ?
C14 C15 C16 C17 0.38(19) ?
C15 C16 C17 C12 -0.61(19) ?
C15 C16 C17 C18 178.97(12) ?
C13 C12 C17 C16 0.09(18) ?
C11 C12 C17 C16 178.97(12) ?
C13 C12 C17 C18 -179.46(12) ?
C11 C12 C17 C18 -0.6(2) ?
C15 C14 C19 O8 -2.3(2) yes
C13 C14 C19 O8 179.28(13) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 61380
2 PubChem 68066
