#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/40/4504091.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4504091
loop_
_publ_author_name
'Jacobs, Ayesha'
'Faleni, Nobathembu'
'Nassimbeni, Luigi R.'
'Taljaard, Jana H.'
_publ_section_title
;
 Inclusion by a Xanthenol Host:  Relating Structure to the Kinetics
 of Desolvation and Guest Exchange
;
_journal_issue                   6
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              1003
_journal_paper_doi               10.1021/cg060792u
_journal_volume                  7
_journal_year                    2007
_chemical_formula_moiety         'C20 H16 O3.C2 H4O1'
_chemical_formula_sum            'C22 H20 O4'
_chemical_formula_weight         348.38
_chemical_name_systematic
; 
 9-(4-methoxyphenyl)-9H-xanthen-9-ol dioxane clathrate  
;
_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                97.04(3)
_cell_angle_beta                 101.33(3)
_cell_angle_gamma                111.15(3)
_cell_formula_units_Z            2
_cell_length_a                   8.4075(17)
_cell_length_b                   9.0908(18)
_cell_length_c                   12.442(3)
_cell_measurement_reflns_used    'All data'
_cell_measurement_temperature    113(2)
_cell_volume                     849.9(4)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (2000)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'X-seed (Barbour, 1999)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      113(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       '1° φ scans 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  0.0254
_diffrn_reflns_av_sigmaI/netI    0.0527
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6199
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.68
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rectangle
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       N/A
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         3422
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0682
_refine_ls_R_factor_gt           0.0396
_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)+(0.0408P)²+0.1420P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0854
_refine_ls_wR_factor_ref         0.0943
_reflns_number_gt                2419
_reflns_number_total             3422
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg060792usi20070228_060148.cif
_cod_data_source_block           c:\ctech_~1\crysta~1\a1diox~1\a1diox
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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-1
_cod_database_code               4504091
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.04953(12) 0.49820(11) 0.37910(8) 0.0156(2) Uani 1 1 d .
C1 C -0.06111(18) 0.20873(17) 0.37069(11) 0.0131(3) Uani 1 1 d .
H1 H -0.203(2) 0.3081(12) 0.5157(11) 0.060(6) Uiso 1 1 d D
O2 O -0.28466(12) 0.20650(11) 0.46622(8) 0.0156(2) Uani 1 1 d D
C2 C -0.01689(19) 0.07639(18) 0.38097(12) 0.0169(3) Uani 1 1 d .
H2 H -0.1085 -0.0276 0.3686 0.020 Uiso 1 1 calc R
O3 O -0.77037(13) -0.40351(12) 0.09403(8) 0.0215(3) Uani 1 1 d .
C3 C 0.15716(19) 0.09288(18) 0.40876(12) 0.0183(3) Uani 1 1 d .
H3 H 0.1841 0.0010 0.4155 0.022 Uiso 1 1 calc R
C4 C 0.29229(19) 0.24402(18) 0.42675(12) 0.0186(3) Uani 1 1 d .
H4 H 0.4120 0.2560 0.4473 0.022 Uiso 1 1 calc R
C5 C 0.25288(19) 0.37691(18) 0.41479(12) 0.0172(3) Uani 1 1 d .
H5 H 0.3448 0.4802 0.4252 0.021 Uiso 1 1 calc R
C6 C 0.07725(18) 0.35790(16) 0.38737(11) 0.0127(3) Uani 1 1 d .
C7 C -0.26662(18) 0.34041(17) 0.31111(12) 0.0138(3) Uani 1 1 d .
C8 C -0.43064(19) 0.34065(17) 0.26087(12) 0.0170(3) Uani 1 1 d .
H8 H -0.5332 0.2434 0.2443 0.020 Uiso 1 1 calc R
C9 C -0.4475(2) 0.47823(18) 0.23468(12) 0.0192(4) Uani 1 1 d .
H9 H -0.5606 0.4756 0.2014 0.023 Uiso 1 1 calc R
C10 C -0.2980(2) 0.62113(18) 0.25715(12) 0.0201(4) Uani 1 1 d .
H10 H -0.3091 0.7167 0.2403 0.024 Uiso 1 1 calc R
C11 C -0.1339(2) 0.62375(18) 0.30377(12) 0.0175(3) Uani 1 1 d .
H11 H -0.0312 0.7202 0.3177 0.021 Uiso 1 1 calc R
C12 C -0.12017(18) 0.48419(17) 0.33025(11) 0.0133(3) Uani 1 1 d .
C13 C -0.24964(18) 0.19731(17) 0.35622(11) 0.0134(3) Uani 1 1 d .
C14 C -0.38693(18) 0.03584(17) 0.28465(12) 0.0132(3) Uani 1 1 d .
C15 C -0.50796(18) -0.07171(17) 0.32892(12) 0.0149(3) Uani 1 1 d .
H15 H -0.5045 -0.0455 0.4059 0.018 Uiso 1 1 calc R
C16 C -0.63305(18) -0.21598(18) 0.26284(12) 0.0157(3) Uani 1 1 d .
H16 H -0.7143 -0.2881 0.2948 0.019 Uiso 1 1 calc R
C17 C -0.64130(18) -0.25668(16) 0.15047(12) 0.0147(3) Uani 1 1 d .
C18 C -0.52091(19) -0.15166(18) 0.10373(12) 0.0166(3) Uani 1 1 d .
H18 H -0.5249 -0.1786 0.0268 0.020 Uiso 1 1 calc R
C19 C -0.39430(19) -0.00615(17) 0.17173(12) 0.0157(3) Uani 1 1 d .
H19 H -0.3117 0.0655 0.1403 0.019 Uiso 1 1 calc R
C20 C -0.7845(2) -0.4525(2) -0.02209(14) 0.0347(5) Uani 1 1 d .
H20A H -0.8107 -0.3750 -0.0631 0.052 Uiso 1 1 calc R
H20B H -0.8797 -0.5598 -0.0519 0.052 Uiso 1 1 calc R
H20C H -0.6727 -0.4564 -0.0310 0.052 Uiso 1 1 calc R
O1G O 0.06260(15) 0.87507(14) -0.01018(9) 0.0329(3) Uani 1 1 d .
C1G C -0.0897(2) 0.8686(2) -0.08914(14) 0.0295(4) Uani 1 1 d .
H1GA H -0.1972 0.8095 -0.0658 0.035 Uiso 1 1 calc R
H1GB H -0.0990 0.8091 -0.1638 0.035 Uiso 1 1 calc R
C2G C 0.0789(2) 0.9653(2) 0.09691(14) 0.0315(4) Uani 1 1 d .
H2GA H 0.1865 0.9727 0.1510 0.038 Uiso 1 1 calc R
H2GB H -0.0243 0.9086 0.1249 0.038 Uiso 1 1 calc R
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_site_symmetry_1
_geom_angle_site_symmetry_3
C6 O1 C12 118.32(11) . .
C6 C1 C2 117.15(13) . .
C6 C1 C13 120.18(13) . .
C2 C1 C13 122.26(13) . .
C13 O2 H1 110.0(10) . .
C3 C2 C1 121.57(14) . .
C3 C2 H2 119.2 . .
C1 C2 H2 119.2 . .
C17 O3 C20 117.64(13) . .
C2 C3 C4 119.83(15) . .
C2 C3 H3 120.1 . .
C4 C3 H3 120.1 . .
C5 C4 C3 120.03(14) . .
C5 C4 H4 120.0 . .
C3 C4 H4 120.0 . .
C4 C5 C6 119.22(14) . .
C4 C5 H5 120.4 . .
C6 C5 H5 120.4 . .
O1 C6 C5 115.46(12) . .
O1 C6 C1 122.36(12) . .
C5 C6 C1 122.18(14) . .
C12 C7 C8 116.90(14) . .
C12 C7 C13 120.62(13) . .
C8 C7 C13 122.06(13) . .
C9 C8 C7 121.74(14) . .
C9 C8 H8 119.1 . .
C7 C8 H8 119.1 . .
C8 C9 C10 119.73(14) . .
C8 C9 H9 120.1 . .
C10 C9 H9 120.1 . .
C11 C10 C9 119.92(15) . .
C11 C10 H10 120.0 . .
C9 C10 H10 120.0 . .
C10 C11 C12 119.37(14) . .
C10 C11 H11 120.3 . .
C12 C11 H11 120.3 . .
C11 C12 C7 122.30(13) . .
C11 C12 O1 115.65(12) . .
C7 C12 O1 122.04(13) . .
O2 C13 C7 107.96(11) . .
O2 C13 C1 107.97(11) . .
C7 C13 C1 109.50(12) . .
O2 C13 C14 105.90(11) . .
C7 C13 C14 112.55(12) . .
C1 C13 C14 112.69(12) . .
C15 C14 C19 118.28(13) . .
C15 C14 C13 121.62(13) . .
C19 C14 C13 120.10(13) . .
C16 C15 C14 120.98(14) . .
C16 C15 H15 119.5 . .
C14 C15 H15 119.5 . .
C15 C16 C17 120.65(14) . .
C15 C16 H16 119.7 . .
C17 C16 H16 119.7 . .
O3 C17 C16 115.12(13) . .
O3 C17 C18 125.16(13) . .
C16 C17 C18 119.72(13) . .
C17 C18 C19 119.07(13) . .
C17 C18 H18 120.5 . .
C19 C18 H18 120.5 . .
C14 C19 C18 121.30(14) . .
C14 C19 H19 119.3 . .
C18 C19 H19 119.3 . .
O3 C20 H20A 109.5 . .
O3 C20 H20B 109.5 . .
H20A C20 H20B 109.5 . .
O3 C20 H20C 109.5 . .
H20A C20 H20C 109.5 . .
H20B C20 H20C 109.5 . .
C1G O1G C2G 109.45(13) . .
O1G C1G C2G 110.91(14) . 2_575
O1G C1G H1GA 109.5 . .
C2G C1G H1GA 109.5 2_575 .
O1G C1G H1GB 109.5 . .
C2G C1G H1GB 109.5 2_575 .
H1GA C1G H1GB 108.0 . .
O1G C2G C1G 110.86(14) . 2_575
O1G C2G H2GA 109.5 . .
C1G C2G H2GA 109.5 2_575 .
O1G C2G H2GB 109.5 . .
C1G C2G H2GB 109.5 2_575 .
H2GA C2G H2GB 108.1 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C6 1.3889(17) .
O1 C12 1.3893(17) .
C1 C6 1.390(2) .
C1 C2 1.394(2) .
C1 C13 1.523(2) .
O2 C13 1.4542(17) .
O2 H1 0.9704(11) .
C2 C3 1.383(2) .
C2 H2 0.9500 .
O3 C17 1.3703(18) .
O3 C20 1.4271(19) .
C3 C4 1.388(2) .
C3 H3 0.9500 .
C4 C5 1.380(2) .
C4 H4 0.9500 .
C5 C6 1.389(2) .
C5 H5 0.9500 .
C7 C12 1.389(2) .
C7 C8 1.399(2) .
C7 C13 1.520(2) .
C8 C9 1.378(2) .
C8 H8 0.9500 .
C9 C10 1.393(2) .
C9 H9 0.9500 .
C10 C11 1.378(2) .
C10 H10 0.9500 .
C11 C12 1.387(2) .
C11 H11 0.9500 .
C13 C14 1.527(2) .
C14 C15 1.389(2) .
C14 C19 1.393(2) .
C15 C16 1.379(2) .
C15 H15 0.9500 .
C16 C17 1.383(2) .
C16 H16 0.9500 .
C17 C18 1.394(2) .
C18 C19 1.398(2) .
C18 H18 0.9500 .
C19 H19 0.9500 .
C20 H20A 0.9800 .
C20 H20B 0.9800 .
C20 H20C 0.9800 .
O1G C1G 1.4302(19) .
O1G C2G 1.430(2) .
C1G C2G 1.497(2) 2_575
C1G H1GA 0.9900 .
C1G H1GB 0.9900 .
C2G C1G 1.497(2) 2_575
C2G H2GA 0.9900 .
C2G H2GB 0.9900 .
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_site_symmetry_4
C6 C1 C2 C3 1.3(2) .
C13 C1 C2 C3 -171.34(13) .
C1 C2 C3 C4 -0.2(2) .
C2 C3 C4 C5 -1.2(2) .
C3 C4 C5 C6 1.6(2) .
C12 O1 C6 C5 167.10(12) .
C12 O1 C6 C1 -13.63(19) .
C4 C5 C6 O1 178.81(12) .
C4 C5 C6 C1 -0.5(2) .
C2 C1 C6 O1 179.85(12) .
C13 C1 C6 O1 -7.4(2) .
C2 C1 C6 C5 -0.9(2) .
C13 C1 C6 C5 171.82(13) .
C12 C7 C8 C9 -2.0(2) .
C13 C7 C8 C9 170.58(14) .
C7 C8 C9 C10 0.8(2) .
C8 C9 C10 C11 1.0(2) .
C9 C10 C11 C12 -1.5(2) .
C10 C11 C12 C7 0.2(2) .
C10 C11 C12 O1 -178.68(13) .
C8 C7 C12 C11 1.5(2) .
C13 C7 C12 C11 -171.19(13) .
C8 C7 C12 O1 -179.67(12) .
C13 C7 C12 O1 7.6(2) .
C6 O1 C12 C11 -167.57(12) .
C6 O1 C12 C7 13.54(19) .
C12 C7 C13 O2 91.65(15) .
C8 C7 C13 O2 -80.67(16) .
C12 C7 C13 C1 -25.66(18) .
C8 C7 C13 C1 162.02(13) .
C12 C7 C13 C14 -151.83(13) .
C8 C7 C13 C14 35.85(19) .
C6 C1 C13 O2 -91.82(15) .
C2 C1 C13 O2 80.55(16) .
C6 C1 C13 C7 25.48(17) .
C2 C1 C13 C7 -162.15(13) .
C6 C1 C13 C14 151.57(13) .
C2 C1 C13 C14 -36.05(18) .
O2 C13 C14 C15 -2.50(18) .
C7 C13 C14 C15 -120.24(15) .
C1 C13 C14 C15 115.33(15) .
O2 C13 C14 C19 176.83(12) .
C7 C13 C14 C19 59.09(18) .
C1 C13 C14 C19 -65.34(17) .
C19 C14 C15 C16 -0.4(2) .
C13 C14 C15 C16 178.95(13) .
C14 C15 C16 C17 -0.3(2) .
C20 O3 C17 C16 -179.59(14) .
C20 O3 C17 C18 -0.7(2) .
C15 C16 C17 O3 179.56(13) .
C15 C16 C17 C18 0.6(2) .
O3 C17 C18 C19 -179.16(14) .
C16 C17 C18 C19 -0.4(2) .
C15 C14 C19 C18 0.7(2) .
C13 C14 C19 C18 -178.67(13) .
C17 C18 C19 C14 -0.3(2) .
C2G O1G C1G C2G 57.4(2) 2_575
C1G O1G C2G C1G -57.3(2) 2_575
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139145432
