#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:05:27 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180286 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/00/7150040.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_7150040
loop_
_publ_author_name
'Jacobs, Ayesha'
'Nassimbeni, Luigi R.'
'Su, Hong'
'Taljaard, Benjamin'
_publ_section_title
;
 Xanthenol clathrates: structure, thermal stability, guest exchange and
 kinetics of desolvation.
;
_journal_issue                   7
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              1319
_journal_page_last               1322
_journal_paper_doi               10.1039/b416331a
_journal_volume                  3
_journal_year                    2005
_chemical_formula_moiety         'C20 H16 O3.C3 H3'
_chemical_formula_sum            'C23 H19 O3'
_chemical_formula_weight         343.38
_chemical_name_common
'9-(4-methoxyphenyl)-9H-xanthen-9-ol benzene clathrate'
_chemical_name_systematic
;
9-(4-methoxyphenyl)-9H-xanthen-9-ol benzene 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                97.4850(10)
_cell_angle_beta                 104.1640(10)
_cell_angle_gamma                109.3880(10)
_cell_formula_units_Z            2
_cell_length_a                   8.37630(10)
_cell_length_b                   9.0965(2)
_cell_length_c                   12.6943(3)
_cell_measurement_reflns_used    'All data'
_cell_measurement_temperature    113(2)
_cell_volume                     860.68(3)
_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, 2001)'
_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 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Nonius Kappa CCD diffractometer'
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0374
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            3760
_diffrn_reflns_theta_full        27.15
_diffrn_reflns_theta_max         27.15
_diffrn_reflns_theta_min         3.62
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.9811
_exptl_absorpt_correction_T_min  0.9644
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Cuboid
_exptl_crystal_F_000             362
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.907
_refine_diff_density_min         -1.047
_refine_diff_density_rms         0.311
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         3760
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.107
_refine_ls_R_factor_all          0.0890
_refine_ls_R_factor_gt           0.0510
_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)+(0.1444P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1457
_refine_ls_wR_factor_ref         0.2044
_reflns_number_gt                2827
_reflns_number_total             3760
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b416331a.txt
_cod_data_source_block           1d
_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_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7150040
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.28905(16) 0.20785(14) 0.46648(9) 0.0158(3) Uani 1 1 d D . .
H1 H -0.202(3) 0.3083(17) 0.5119(17) 0.053(8) Uiso 1 1 d D . .
O2 O 0.04041(16) 0.49751(14) 0.38198(10) 0.0174(3) Uani 1 1 d . . .
H2 H -0.5492 0.2498 0.2479 0.022 Uiso 1 1 calc R . .
O3 O -0.78248(17) -0.37923(15) 0.07014(10) 0.0225(4) Uani 1 1 d . . .
C1 C -0.2785(2) 0.3447(2) 0.31624(14) 0.0148(4) Uani 1 1 d . . .
C2 C -0.4469(2) 0.3453(2) 0.26478(16) 0.0187(4) Uani 1 1 d . . .
C3 C -0.4670(3) 0.4820(2) 0.23825(16) 0.0224(5) Uani 1 1 d . . .
H3 H -0.5822 0.4803 0.2042 0.027 Uiso 1 1 calc R . .
C4 C -0.3178(3) 0.6224(2) 0.26147(16) 0.0209(4) Uani 1 1 d . . .
H4 H -0.3314 0.7172 0.2447 0.025 Uiso 1 1 calc R . .
C5 C -0.1503(3) 0.6237(2) 0.30885(15) 0.0188(4) Uani 1 1 d . . .
H5 H -0.0479 0.7184 0.3233 0.023 Uiso 1 1 calc R . .
C6 C -0.1329(2) 0.4850(2) 0.33519(14) 0.0150(4) Uani 1 1 d . . .
C7 C -0.0665(2) 0.2123(2) 0.37574(14) 0.0136(4) Uani 1 1 d . . .
C8 C -0.0202(2) 0.0804(2) 0.38718(15) 0.0170(4) Uani 1 1 d . . .
H8 H -0.1113 -0.0214 0.3756 0.020 Uiso 1 1 calc R . .
C9 C 0.1561(2) 0.0942(2) 0.41511(15) 0.0186(4) Uani 1 1 d . . .
H9 H 0.1847 0.0027 0.4228 0.022 Uiso 1 1 calc R . .
C10 C 0.2901(2) 0.2423(2) 0.43169(15) 0.0196(4) Uani 1 1 d . . .
H10 H 0.4110 0.2528 0.4522 0.023 Uiso 1 1 calc R . .
C11 C 0.2475(2) 0.3742(2) 0.41826(15) 0.0185(4) Uani 1 1 d . . .
H11 H 0.3384 0.4753 0.4275 0.022 Uiso 1 1 calc R . .
C12 C 0.0703(2) 0.3579(2) 0.39107(14) 0.0145(4) Uani 1 1 d . . .
C13 C -0.2565(2) 0.2018(2) 0.35904(14) 0.0143(4) Uani 1 1 d . . .
C14 C -0.3941(2) 0.0431(2) 0.28244(14) 0.0140(4) Uani 1 1 d . . .
C15 C -0.5226(2) -0.0612(2) 0.31847(15) 0.0168(4) Uani 1 1 d . . .
H15 H -0.5231 -0.0363 0.3934 0.020 Uiso 1 1 calc R . .
C16 C -0.6499(2) -0.2012(2) 0.24535(16) 0.0186(4) Uani 1 1 d . . .
H16 H -0.7367 -0.2720 0.2706 0.022 Uiso 1 1 calc R . .
C17 C -0.6509(2) -0.2384(2) 0.13550(15) 0.0166(4) Uani 1 1 d . . .
C18 C -0.5210(2) -0.1371(2) 0.09900(15) 0.0180(4) Uani 1 1 d . . .
H18 H -0.5192 -0.1631 0.0245 0.022 Uiso 1 1 calc R . .
C19 C -0.3943(2) 0.0024(2) 0.17294(15) 0.0169(4) Uani 1 1 d . . .
H19 H -0.3056 0.0716 0.1482 0.020 Uiso 1 1 calc R . .
C20 C -0.7928(3) -0.4178(3) -0.04425(17) 0.0346(6) Uani 1 1 d . . .
H20A H -0.8016 -0.3290 -0.0784 0.052 Uiso 1 1 calc R . .
H20B H -0.8980 -0.5151 -0.0833 0.052 Uiso 1 1 calc R . .
H20C H -0.6858 -0.4358 -0.0498 0.052 Uiso 1 1 calc R . .
C1G C 0.0158(3) 0.0777(3) -0.08528(19) 0.0390(6) Uani 1 1 d . . .
H1G H 0.0273 0.1319 -0.1438 0.047 Uiso 1 1 calc R . .
C2G C -0.0548(3) -0.0865(3) -0.10913(18) 0.0341(6) Uani 1 1 d . . .
H2G H -0.0928 -0.1459 -0.1841 0.041 Uiso 1 1 calc R . .
C3G C -0.0707(3) -0.1650(3) -0.0242(2) 0.0403(6) Uani 1 1 d . . .
H3G H -0.1191 -0.2788 -0.0404 0.048 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
_geom_angle_publ_flag
O1 C13 C1 108.49(13) . . ?
O1 C13 C14 106.14(13) . . ?
O1 C13 C7 108.33(13) . . ?
O2 C12 C11 115.43(15) . . ?
O2 C6 C5 115.20(15) . . ?
O3 C17 C16 115.67(16) . . ?
O3 C17 C18 124.30(16) . . ?
O3 C20 H20A 109.5 . . ?
O3 C20 H20B 109.5 . . ?
O3 C20 H20C 109.5 . . ?
C1 C13 C14 111.75(14) . . ?
C1 C13 C7 109.52(14) . . ?
C1 C2 H2 119.3 . . ?
C1 C6 C5 122.26(17) . . ?
C1 C6 O2 122.54(16) . . ?
C2 C1 C13 121.81(15) . . ?
C2 C3 C4 119.83(18) . . ?
C2 C3 H3 120.1 . . ?
C3 C2 C1 121.38(17) . . ?
C3 C2 H2 119.3 . . ?
C3 C4 H4 120.0 . . ?
C4 C3 H3 120.1 . . ?
C4 C5 C6 119.32(17) . . ?
C4 C5 H5 120.3 . . ?
C5 C4 C3 119.95(17) . . ?
C5 C4 H4 120.0 . . ?
C6 C1 C13 120.79(16) . . ?
C6 C1 C2 117.19(16) . . ?
C6 C5 H5 120.3 . . ?
C7 C12 C11 122.11(16) . . ?
C7 C12 O2 122.46(16) . . ?
C7 C13 C14 112.43(14) . . ?
C7 C8 H8 119.2 . . ?
C8 C7 C13 121.61(15) . . ?
C8 C9 H9 120.1 . . ?
C9 C10 H10 120.1 . . ?
C9 C8 C7 121.58(17) . . ?
C9 C8 H8 119.2 . . ?
C10 C11 C12 119.44(17) . . ?
C10 C11 H11 120.3 . . ?
C10 C9 C8 119.70(17) . . ?
C10 C9 H9 120.1 . . ?
C11 C10 C9 119.88(17) . . ?
C11 C10 H10 120.1 . . ?
C12 C11 H11 120.3 . . ?
C12 C7 C13 120.82(15) . . ?
C12 C7 C8 117.27(16) . . ?
C12 O2 C6 118.19(14) . . ?
C13 O1 H1 104.0(15) . . ?
C14 C15 H15 119.9 . . ?
C14 C19 H19 119.2 . . ?
C15 C14 C13 121.85(15) . . ?
C15 C16 C17 120.32(17) . . ?
C15 C16 H16 119.8 . . ?
C16 C15 C14 120.30(17) . . ?
C16 C15 H15 119.9 . . ?
C16 C17 C18 120.01(16) . . ?
C17 C16 H16 119.8 . . ?
C17 C18 H18 120.4 . . ?
C17 O3 C20 117.28(14) . . ?
C18 C19 C14 121.50(17) . . ?
C18 C19 H19 119.2 . . ?
C19 C14 C13 119.41(15) . . ?
C19 C14 C15 118.73(16) . . ?
C19 C18 C17 119.12(17) . . ?
C19 C18 H18 120.4 . . ?
C1G C2G C3G 119.9(2) . . ?
C1G C2G H2G 120.1 . . ?
C1G C3G H3G 120.0 2 . ?
C2G C1G C3G 120.2(2) . 2 ?
C2G C1G H1G 119.9 . . ?
C2G C3G C1G 119.9(2) . 2 ?
C2G C3G H3G 120.0 . . ?
C3G C1G H1G 119.9 2 . ?
C3G C2G H2G 120.1 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C13 1.4525(19) . ?
O1 H1 0.955(7) . ?
O2 C12 1.387(2) . ?
O2 C6 1.387(2) . ?
O3 C17 1.372(2) . ?
O3 C20 1.423(2) . ?
C1 C2 1.404(3) . ?
C1 C6 1.384(3) . ?
C2 C3 1.381(3) . ?
C2 H2 0.9500 . ?
C3 H3 0.9500 . ?
C4 C3 1.393(3) . ?
C4 H4 0.9500 . ?
C5 C4 1.380(3) . ?
C5 C6 1.391(2) . ?
C5 H5 0.9500 . ?
C7 C12 1.386(3) . ?
C7 C8 1.392(2) . ?
C8 C9 1.390(2) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C11 1.381(3) . ?
C10 C9 1.388(3) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C11 1.391(3) . ?
C13 C1 1.521(2) . ?
C13 C7 1.522(2) . ?
C14 C13 1.530(2) . ?
C14 C15 1.394(2) . ?
C14 C19 1.391(2) . ?
C15 H15 0.9500 . ?
C16 C15 1.388(3) . ?
C16 C17 1.389(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.393(2) . ?
C18 H18 0.9500 . ?
C19 C18 1.388(3) . ?
C19 H19 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C1G C3G 1.389(3) 2 ?
C1G H1G 0.9500 . ?
C2G C1G 1.371(3) . ?
C2G C3G 1.378(3) . ?
C2G H2G 0.9500 . ?
C3G C1G 1.389(3) 2 ?
C3G H3G 0.9500 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O2 0.955(7) 1.915(7) 2.8655(16) 173(2) 2_566
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_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C13 C1 C2 -79.8(2) . . . . ?
O1 C13 C1 C6 94.69(18) . . . . ?
O1 C13 C7 C12 -95.49(18) . . . . ?
O1 C13 C7 C8 78.12(19) . . . . ?
O2 C12 C11 C10 178.47(14) . . . . ?
O3 C17 C18 C19 -179.88(16) . . . . ?
C1 C13 C7 C12 22.7(2) . . . . ?
C1 C13 C7 C8 -163.72(15) . . . . ?
C1 C2 C3 C4 0.7(3) . . . . ?
C2 C1 C6 C5 2.4(3) . . . . ?
C2 C1 C6 O2 -177.81(15) . . . . ?
C4 C5 C6 C1 -0.5(3) . . . . ?
C4 C5 C6 O2 179.72(16) . . . . ?
C5 C4 C3 C2 1.3(3) . . . . ?
C6 C1 C2 C3 -2.5(3) . . . . ?
C6 C5 C4 C3 -1.4(3) . . . . ?
C6 O2 C12 C11 168.19(14) . . . . ?
C6 O2 C12 C7 -12.7(2) . . . . ?
C7 C12 C11 C10 -0.6(3) . . . . ?
C7 C13 C1 C2 162.16(15) . . . . ?
C7 C13 C1 C6 -23.4(2) . . . . ?
C7 C8 C9 C10 -0.3(3) . . . . ?
C8 C7 C12 C11 -0.8(3) . . . . ?
C8 C7 C12 O2 -179.90(14) . . . . ?
C9 C10 C11 C12 1.7(3) . . . . ?
C11 C10 C9 C8 -1.2(3) . . . . ?
C12 C7 C8 C9 1.3(3) . . . . ?
C12 O2 C6 C1 12.0(2) . . . . ?
C12 O2 C6 C5 -168.20(14) . . . . ?
C13 C1 C2 C3 172.15(16) . . . . ?
C13 C1 C6 C5 -172.35(15) . . . . ?
C13 C1 C6 O2 7.5(3) . . . . ?
C13 C14 C15 C16 177.39(16) . . . . ?
C13 C14 C19 C18 -177.27(16) . . . . ?
C13 C7 C12 C11 173.03(15) . . . . ?
C13 C7 C12 O2 -6.0(3) . . . . ?
C13 C7 C8 C9 -172.51(16) . . . . ?
C14 C13 C1 C2 36.9(2) . . . . ?
C14 C13 C1 C6 -148.63(16) . . . . ?
C14 C13 C7 C12 147.54(16) . . . . ?
C14 C13 C7 C8 -38.8(2) . . . . ?
C14 C19 C18 C17 0.0(3) . . . . ?
C15 C14 C13 C1 -115.84(17) . . . . ?
C15 C14 C13 C7 120.52(17) . . . . ?
C15 C14 C13 O1 2.3(2) . . . . ?
C15 C14 C19 C18 1.4(3) . . . . ?
C15 C16 C17 C18 1.7(3) . . . . ?
C15 C16 C17 O3 -179.83(15) . . . . ?
C16 C17 C18 C19 -1.6(3) . . . . ?
C17 C16 C15 C14 -0.3(3) . . . . ?
C19 C14 C13 C1 62.7(2) . . . . ?
C19 C14 C13 C7 -60.9(2) . . . . ?
C19 C14 C13 O1 -179.15(14) . . . . ?
C19 C14 C15 C16 -1.2(3) . . . . ?
C20 O3 C17 C16 177.24(17) . . . . ?
C20 O3 C17 C18 -4.4(3) . . . . ?
C1G C2G C3G C1G 0.3(4) . . . 2 ?
C3G C2G C1G C3G -0.3(4) . . . 2 ?
