#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/40/4504090.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_4504090
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.C3 H6'
_chemical_formula_sum            'C23 H22 O3'
_chemical_formula_weight         346.41
_chemical_name_systematic
; 
 9-(4-methoxyphenyl)-9H-xanthen-9-ol cyclohexane 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                96.10(3)
_cell_angle_beta                 104.73(3)
_cell_angle_gamma                110.41(3)
_cell_formula_units_Z            2
_cell_length_a                   8.4834(17)
_cell_length_b                   9.1242(18)
_cell_length_c                   12.712(3)
_cell_measurement_reflns_used    'All data'
_cell_measurement_temperature    113(2)
_cell_volume                     871.0(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 0.992
_diffrn_measured_fraction_theta_max 0.992
_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  0.0166
_diffrn_reflns_av_sigmaI/netI    0.0413
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5676
_diffrn_reflns_theta_full        25.64
_diffrn_reflns_theta_max         25.64
_diffrn_reflns_theta_min         2.44
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rectangle
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       N/A
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         3263
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0523
_refine_ls_R_factor_gt           0.0383
_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)+(0.0584P)²+0.0544P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0955
_refine_ls_wR_factor_ref         0.1026
_reflns_number_gt                2572
_reflns_number_total             3263
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg060792usi20070228_060148.cif
_cod_data_source_block           c:\ctech_~1\crysta~1\a1cyclo\a1cyclo
_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               4504090
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 0.04016(11) 0.50086(9) 0.87964(7) 0.0199(2) Uani 1 1 d .
C1 C -0.27840(16) 0.34737(15) 0.81715(10) 0.0169(3) Uani 1 1 d .
H1 H -0.2030(17) 0.3050(11) 1.0182(10) 0.050(5) Uiso 1 1 d D
O2 O -0.28791(11) 0.20705(10) 0.96774(6) 0.0188(2) Uani 1 1 d D
C2 C -0.44531(17) 0.34858(16) 0.76848(10) 0.0198(3) Uani 1 1 d .
H2 H -0.5477 0.2534 0.7543 0.024 Uiso 1 1 calc R
O3 O -0.78185(12) -0.38164(11) 0.57621(7) 0.0251(2) Uani 1 1 d .
C3 C -0.46491(18) 0.48503(16) 0.74047(11) 0.0234(3) Uani 1 1 d .
H3 H -0.5797 0.4834 0.7083 0.028 Uiso 1 1 calc R
C4 C -0.31552(18) 0.62486(16) 0.75962(11) 0.0236(3) Uani 1 1 d .
H4 H -0.3285 0.7192 0.7414 0.028 Uiso 1 1 calc R
C5 C -0.14860(17) 0.62627(16) 0.80507(11) 0.0209(3) Uani 1 1 d .
H5 H -0.0462 0.7205 0.8168 0.025 Uiso 1 1 calc R
C6 C -0.13250(16) 0.48814(15) 0.83346(10) 0.0176(3) Uani 1 1 d .
C7 C -0.06936(16) 0.21471(15) 0.87595(10) 0.0166(3) Uani 1 1 d .
C8 C -0.02423(17) 0.08270(16) 0.88729(10) 0.0190(3) Uani 1 1 d .
H8 H -0.1154 -0.0197 0.8757 0.023 Uiso 1 1 calc R
C9 C 0.15001(17) 0.09727(16) 0.91500(10) 0.0211(3) Uani 1 1 d .
H9 H 0.1774 0.0057 0.9225 0.025 Uiso 1 1 calc R
C10 C 0.28499(17) 0.24645(16) 0.93181(10) 0.0216(3) Uani 1 1 d .
H10 H 0.4049 0.2573 0.9525 0.026 Uiso 1 1 calc R
C11 C 0.24444(17) 0.37872(16) 0.91840(10) 0.0206(3) Uani 1 1 d .
H11 H 0.3357 0.4805 0.9281 0.025 Uiso 1 1 calc R
C12 C 0.06855(16) 0.36104(15) 0.89057(10) 0.0170(3) Uani 1 1 d .
C13 C -0.25762(16) 0.20323(15) 0.86015(10) 0.0167(3) Uani 1 1 d .
C14 C -0.39693(16) 0.04563(15) 0.78453(10) 0.0161(3) Uani 1 1 d .
C15 C -0.52308(16) -0.06194(15) 0.82110(10) 0.0190(3) Uani 1 1 d .
H15 H -0.5223 -0.0386 0.8959 0.023 Uiso 1 1 calc R
C16 C -0.64959(17) -0.20246(15) 0.74960(11) 0.0203(3) Uani 1 1 d .
H16 H -0.7350 -0.2744 0.7757 0.024 Uiso 1 1 calc R
C17 C -0.65236(16) -0.23881(15) 0.64007(10) 0.0181(3) Uani 1 1 d .
C18 C -0.52659(17) -0.13357(15) 0.60229(10) 0.0190(3) Uani 1 1 d .
H18 H -0.5265 -0.1577 0.5278 0.023 Uiso 1 1 calc R
C19 C -0.40103(16) 0.00732(15) 0.67488(10) 0.0180(3) Uani 1 1 d .
H19 H -0.3157 0.0794 0.6488 0.022 Uiso 1 1 calc R
C20 C -0.7827(2) -0.42796(18) 0.46545(11) 0.0319(4) Uani 1 1 d .
H20A H -0.8010 -0.3487 0.4228 0.048 Uiso 1 1 calc R
H20B H -0.8785 -0.5330 0.4301 0.048 Uiso 1 1 calc R
H20C H -0.6690 -0.4341 0.4672 0.048 Uiso 1 1 calc R
C1G C 0.0539(2) 0.11520(19) 0.60489(12) 0.0358(4) Uani 1 1 d .
H1GA H 0.1346 0.1650 0.6819 0.043 Uiso 1 1 calc R
H1GB H -0.0334 0.1655 0.5893 0.043 Uiso 1 1 calc R
C2G C -0.04219(19) -0.06339(19) 0.59510(12) 0.0322(4) Uani 1 1 d .
H2GB H 0.0456 -0.1118 0.6177 0.039 Uiso 1 1 calc R
H2GA H -0.1149 -0.0801 0.6460 0.039 Uiso 1 1 calc R
C3G C 0.1603(2) 0.14512(19) 0.52325(12) 0.0352(4) Uani 1 1 d .
H3GA H 0.2169 0.2617 0.5283 0.042 Uiso 1 1 calc R
H3GB H 0.2551 0.1039 0.5434 0.042 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
C6 O1 C12 118.31(10) .
C6 C1 C2 117.07(12) .
C6 C1 C13 121.16(11) .
C2 C1 C13 121.53(11) .
C13 O2 H1 109.0(10) .
C3 C2 C1 121.58(12) .
C3 C2 H2 119.2 .
C1 C2 H2 119.2 .
C17 O3 C20 117.73(10) .
C2 C3 C4 119.72(13) .
C2 C3 H3 120.1 .
C4 C3 H3 120.1 .
C5 C4 C3 120.02(13) .
C5 C4 H4 120.0 .
C3 C4 H4 120.0 .
C4 C5 C6 119.14(12) .
C4 C5 H5 120.4 .
C6 C5 H5 120.4 .
C1 C6 C5 122.43(12) .
C1 C6 O1 122.34(11) .
C5 C6 O1 115.23(11) .
C12 C7 C8 116.89(12) .
C12 C7 C13 121.11(12) .
C8 C7 C13 121.71(11) .
C9 C8 C7 121.67(12) .
C9 C8 H8 119.2 .
C7 C8 H8 119.2 .
C8 C9 C10 119.82(13) .
C8 C9 H9 120.1 .
C10 C9 H9 120.1 .
C11 C10 C9 119.94(12) .
C11 C10 H10 120.0 .
C9 C10 H10 120.0 .
C10 C11 C12 119.16(12) .
C10 C11 H11 120.4 .
C12 C11 H11 120.4 .
C11 C12 C7 122.48(12) .
C11 C12 O1 115.22(11) .
C7 C12 O1 122.29(11) .
O2 C13 C7 108.44(10) .
O2 C13 C1 108.41(10) .
C7 C13 C1 109.39(10) .
O2 C13 C14 106.09(9) .
C7 C13 C14 112.65(11) .
C1 C13 C14 111.68(10) .
C19 C14 C15 118.14(12) .
C19 C14 C13 119.55(11) .
C15 C14 C13 122.30(11) .
C16 C15 C14 120.75(12) .
C16 C15 H15 119.6 .
C14 C15 H15 119.6 .
C15 C16 C17 120.43(12) .
C15 C16 H16 119.8 .
C17 C16 H16 119.8 .
O3 C17 C16 115.97(11) .
O3 C17 C18 124.35(12) .
C16 C17 C18 119.67(12) .
C19 C18 C17 119.22(12) .
C19 C18 H18 120.4 .
C17 C18 H18 120.4 .
C14 C19 C18 121.79(12) .
C14 C19 H19 119.1 .
C18 C19 H19 119.1 .
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 .
C2G C1G C3G 110.77(13) .
C2G C1G H1GA 109.5 .
C3G C1G H1GA 109.5 .
C2G C1G H1GB 109.5 .
C3G C1G H1GB 109.5 .
H1GA C1G H1GB 108.1 .
C3G C2G C1G 110.94(13) 2_556
C3G C2G H2GB 109.5 2_556
C1G C2G H2GB 109.5 .
C3G C2G H2GA 109.5 2_556
C1G C2G H2GA 109.5 .
H2GB C2G H2GA 108.0 .
C2G C3G C1G 110.90(13) 2_556
C2G C3G H3GA 109.5 2_556
C1G C3G H3GA 109.5 .
C2G C3G H3GB 109.5 2_556
C1G C3G H3GB 109.5 .
H3GA C3G H3GB 108.0 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C6 1.3904(15) .
O1 C12 1.3927(15) .
C1 C6 1.3888(19) .
C1 C2 1.3982(18) .
C1 C13 1.5248(17) .
O2 C13 1.4535(14) .
O2 H1 0.9608(11) .
C2 C3 1.3831(19) .
C2 H2 0.9500 .
O3 C17 1.3739(17) .
O3 C20 1.4240(16) .
C3 C4 1.394(2) .
C3 H3 0.9500 .
C4 C5 1.3817(19) .
C4 H4 0.9500 .
C5 C6 1.3888(18) .
C5 H5 0.9500 .
C7 C12 1.3904(19) .
C7 C8 1.3960(18) .
C7 C13 1.5224(17) .
C8 C9 1.3838(18) .
C8 H8 0.9500 .
C9 C10 1.3915(19) .
C9 H9 0.9500 .
C10 C11 1.3811(18) .
C10 H10 0.9500 .
C11 C12 1.3890(18) .
C11 H11 0.9500 .
C13 C14 1.5271(19) .
C14 C19 1.3892(17) .
C14 C15 1.3935(18) .
C15 C16 1.385(2) .
C15 H15 0.9500 .
C16 C17 1.3890(18) .
C16 H16 0.9500 .
C17 C18 1.3910(18) .
C18 C19 1.390(2) .
C18 H18 0.9500 .
C19 H19 0.9500 .
C20 H20A 0.9800 .
C20 H20B 0.9800 .
C20 H20C 0.9800 .
C1G C2G 1.521(2) .
C1G C3G 1.527(2) .
C1G H1GA 0.9900 .
C1G H1GB 0.9900 .
C2G C3G 1.516(2) 2_556
C2G H2GB 0.9900 .
C2G H2GA 0.9900 .
C3G C2G 1.516(2) 2_556
C3G H3GA 0.9900 .
C3G H3GB 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 -1.69(18) .
C13 C1 C2 C3 172.88(11) .
C1 C2 C3 C4 0.8(2) .
C2 C3 C4 C5 0.8(2) .
C3 C4 C5 C6 -1.44(19) .
C2 C1 C6 C5 1.07(18) .
C13 C1 C6 C5 -173.53(11) .
C2 C1 C6 O1 -179.08(10) .
C13 C1 C6 O1 6.33(18) .
C4 C5 C6 C1 0.48(19) .
C4 C5 C6 O1 -179.39(11) .
C12 O1 C6 C1 12.10(17) .
C12 O1 C6 C5 -168.04(10) .
C12 C7 C8 C9 1.85(18) .
C13 C7 C8 C9 -172.07(11) .
C7 C8 C9 C10 -0.26(19) .
C8 C9 C10 C11 -1.43(19) .
C9 C10 C11 C12 1.42(18) .
C10 C11 C12 C7 0.26(19) .
C10 C11 C12 O1 179.50(10) .
C8 C7 C12 C11 -1.86(18) .
C13 C7 C12 C11 172.09(11) .
C8 C7 C12 O1 178.95(10) .
C13 C7 C12 O1 -7.10(18) .
C6 O1 C12 C11 169.04(10) .
C6 O1 C12 C7 -11.72(16) .
C12 C7 C13 O2 -95.37(13) .
C8 C7 C13 O2 78.29(14) .
C12 C7 C13 C1 22.68(15) .
C8 C7 C13 C1 -163.65(11) .
C12 C7 C13 C14 147.52(11) .
C8 C7 C13 C14 -38.81(15) .
C6 C1 C13 O2 95.74(13) .
C2 C1 C13 O2 -78.61(14) .
C6 C1 C13 C7 -22.34(15) .
C2 C1 C13 C7 163.32(11) .
C6 C1 C13 C14 -147.74(11) .
C2 C1 C13 C14 37.91(15) .
O2 C13 C14 C19 -179.77(10) .
C7 C13 C14 C19 -61.28(14) .
C1 C13 C14 C19 62.30(14) .
O2 C13 C14 C15 0.99(16) .
C7 C13 C14 C15 119.48(12) .
C1 C13 C14 C15 -116.94(12) .
C19 C14 C15 C16 -0.46(18) .
C13 C14 C15 C16 178.79(11) .
C14 C15 C16 C17 0.23(19) .
C20 O3 C17 C16 -176.29(12) .
C20 O3 C17 C18 2.71(18) .
C15 C16 C17 O3 179.37(11) .
C15 C16 C17 C18 0.32(19) .
O3 C17 C18 C19 -179.60(11) .
C16 C17 C18 C19 -0.63(19) .
C15 C14 C19 C18 0.14(18) .
C13 C14 C19 C18 -179.13(11) .
C17 C18 C19 C14 0.40(19) .
C3G C1G C2G C3G -56.37(19) 2_556
C2G C1G C3G C2G 56.4(2) 2_556
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139145431
