#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:05:27 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180286 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/00/7150042.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_7150042
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.C4 H5'
_chemical_formula_sum            'C24 H21 O3'
_chemical_formula_weight         357.41
_chemical_name_common
'9-(4-methoxyphenyl)-9H-xanthen-9-ol o-xylene clathrate'
_chemical_name_systematic
;
9-(4-methoxyphenyl)-9H-xanthen-9-ol o-xylene 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                96.6960(10)
_cell_angle_beta                 94.0480(10)
_cell_angle_gamma                109.7170(10)
_cell_formula_units_Z            2
_cell_length_a                   8.36540(10)
_cell_length_b                   9.06520(10)
_cell_length_c                   12.8730(3)
_cell_measurement_reflns_used    'All data'
_cell_measurement_temperature    113(2)
_cell_volume                     906.38(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 0.989
_diffrn_measured_fraction_theta_max 0.989
_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  0.0108
_diffrn_reflns_av_sigmaI/netI    0.0233
_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       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7595
_diffrn_reflns_theta_full        27.44
_diffrn_reflns_theta_max         27.44
_diffrn_reflns_theta_min         3.21
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.9831
_exptl_absorpt_correction_T_min  0.9716
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cuboid
_exptl_crystal_F_000             378
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         1.741
_refine_diff_density_min         -1.089
_refine_diff_density_rms         0.102
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         4095
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0990
_refine_ls_R_factor_gt           0.0904
_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)+(0.0911P)²+2.6123P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2273
_refine_ls_wR_factor_ref         0.2341
_reflns_number_gt                3609
_reflns_number_total             4095
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b416331a.txt
_cod_data_source_block           c:\opix\myexam~1\a1oxy\a1oxy
_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               7150042
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 -0.2808(2) 0.2134(2) 0.46869(14) 0.0163(4) Uani 1 1 d D . .
C1 C -0.0305(3) 0.2280(3) 0.38218(19) 0.0148(5) Uani 1 1 d . . .
H1 H -0.209(5) 0.304(3) 0.518(3) 0.051(12) Uiso 1 1 d D . .
O2 O 0.0796(2) 0.5136(2) 0.38408(15) 0.0189(4) Uani 1 1 d . . .
C2 C 0.0105(3) 0.0930(3) 0.3935(2) 0.0188(5) Uani 1 1 d . . .
H2 H -0.0782 -0.0078 0.3825 0.023 Uiso 1 1 calc R . .
C3 C 0.1772(3) 0.1026(3) 0.4204(2) 0.0207(6) Uani 1 1 d . . .
H3 H 0.2021 0.0094 0.4281 0.025 Uiso 1 1 calc R . .
C4 C 0.3083(3) 0.2495(3) 0.4362(2) 0.0203(5) Uani 1 1 d . . .
H4 H 0.4225 0.2567 0.4561 0.024 Uiso 1 1 calc R . .
C5 C 0.2727(3) 0.3853(3) 0.4229(2) 0.0193(5) Uani 1 1 d . . .
H5 H 0.3620 0.4856 0.4323 0.023 Uiso 1 1 calc R . .
C6 C 0.1041(3) 0.3720(3) 0.39555(19) 0.0157(5) Uani 1 1 d . . .
C7 C -0.2224(3) 0.3695(3) 0.32676(19) 0.0149(5) Uani 1 1 d . . .
C8 C -0.3762(3) 0.3778(3) 0.2818(2) 0.0182(5) Uani 1 1 d . . .
H8 H -0.4759 0.2852 0.2700 0.022 Uiso 1 1 calc R . .
C9 C -0.3858(4) 0.5179(3) 0.2544(2) 0.0210(6) Uani 1 1 d . . .
H9 H -0.4919 0.5215 0.2255 0.025 Uiso 1 1 calc R . .
C10 C -0.2399(4) 0.6535(3) 0.2690(2) 0.0218(6) Uani 1 1 d . . .
H10 H -0.2462 0.7496 0.2499 0.026 Uiso 1 1 calc R . .
C11 C -0.0859(3) 0.6482(3) 0.3114(2) 0.0202(5) Uani 1 1 d . . .
H11 H 0.0143 0.7401 0.3208 0.024 Uiso 1 1 calc R . .
C12 C -0.0793(3) 0.5067(3) 0.3401(2) 0.0163(5) Uani 1 1 d . . .
C13 C -0.2153(3) 0.2203(3) 0.36742(19) 0.0136(5) Uani 1 1 d . . .
C14 C -0.3309(3) 0.0708(3) 0.29505(19) 0.0143(5) Uani 1 1 d . . .
C15 C -0.4677(3) -0.0416(3) 0.3299(2) 0.0167(5) Uani 1 1 d . . .
H15 H -0.4888 -0.0276 0.4013 0.020 Uiso 1 1 calc R . .
C16 C -0.5734(3) -0.1737(3) 0.2612(2) 0.0193(5) Uani 1 1 d . . .
H16 H -0.6659 -0.2499 0.2859 0.023 Uiso 1 1 calc R . .
C17 C -0.5447(3) -0.1951(3) 0.1565(2) 0.0184(5) Uani 1 1 d . . .
C18 C -0.4072(4) -0.0850(3) 0.1207(2) 0.0196(5) Uani 1 1 d . . .
H18 H -0.3858 -0.0994 0.0494 0.023 Uiso 1 1 calc R . .
C19 C -0.3016(3) 0.0463(3) 0.1905(2) 0.0180(5) Uani 1 1 d . . .
H19 H -0.2072 0.1210 0.1663 0.022 Uiso 1 1 calc R . .
O3 O -0.6566(3) -0.3290(2) 0.09508(16) 0.0265(5) Uani 1 1 d . . .
C20 C -0.6335(5) -0.3511(4) -0.0137(2) 0.0330(7) Uani 1 1 d . . .
H20A H -0.6378 -0.2590 -0.0452 0.049 Uiso 1 1 calc R . .
H20B H -0.7245 -0.4467 -0.0501 0.049 Uiso 1 1 calc R . .
H20C H -0.5222 -0.3627 -0.0204 0.049 Uiso 1 1 calc R . .
C1G C 0.1632(11) 0.1851(10) 0.1329(7) 0.0447(17) Uiso 0.50 1 d P . .
C2G C 0.0939(11) 0.2645(10) 0.0638(7) 0.0457(18) Uiso 0.50 1 d P . .
C3G C 0.0063(9) 0.2045(8) -0.0183(6) 0.0871(18) Uiso 1 1 d . . .
C4G C -0.0379(6) 0.0357(6) -0.0369(4) 0.0586(11) Uiso 1 1 d . . .
C5G C -0.1568(9) -0.0586(8) -0.1279(6) 0.0873(18) Uiso 1 1 d . . .
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
C13 O1 H1 110(3) . . ?
C6 C1 C2 117.2(2) . . ?
C6 C1 C13 121.1(2) . . ?
C2 C1 C13 121.4(2) . . ?
C12 O2 C6 118.15(19) . . ?
C3 C2 C1 121.6(2) . . ?
C3 C2 H2 119.2 . . ?
C1 C2 H2 119.2 . . ?
C2 C3 C4 119.7(2) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 120.2(2) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 118.8(2) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
O2 C6 C1 122.4(2) . . ?
O2 C6 C5 115.1(2) . . ?
C1 C6 C5 122.5(2) . . ?
C12 C7 C8 117.2(2) . . ?
C12 C7 C13 121.2(2) . . ?
C8 C7 C13 121.5(2) . . ?
C9 C8 C7 121.4(2) . . ?
C9 C8 H8 119.3 . . ?
C7 C8 H8 119.3 . . ?
C8 C9 C10 119.9(2) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C11 C10 C9 120.0(2) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C12 119.3(2) . . ?
C10 C11 H11 120.4 . . ?
C12 C11 H11 120.4 . . ?
O2 C12 C7 122.6(2) . . ?
O2 C12 C11 115.2(2) . . ?
C7 C12 C11 122.2(2) . . ?
O1 C13 C1 108.59(19) . . ?
O1 C13 C7 108.74(19) . . ?
C1 C13 C7 109.4(2) . . ?
O1 C13 C14 106.23(19) . . ?
C1 C13 C14 112.39(19) . . ?
C7 C13 C14 111.39(19) . . ?
C19 C14 C15 118.5(2) . . ?
C19 C14 C13 119.4(2) . . ?
C15 C14 C13 122.0(2) . . ?
C16 C15 C14 120.5(2) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C17 C16 C15 120.4(2) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
O3 C17 C16 115.8(2) . . ?
O3 C17 C18 124.3(2) . . ?
C16 C17 C18 119.9(2) . . ?
C19 C18 C17 119.2(2) . . ?
C19 C18 H18 120.4 . . ?
C17 C18 H18 120.4 . . ?
C14 C19 C18 121.5(2) . . ?
C14 C19 H19 119.2 . . ?
C18 C19 H19 119.2 . . ?
C17 O3 C20 117.0(2) . . ?
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 . . ?
C5G C1G C2G 132.2(9) 2 . ?
C3G C2G C1G 125.6(8) . . ?
C2G C3G C4G 112.8(7) . . ?
C3G C4G C4G 117.9(6) . 2 ?
C3G C4G C5G 120.4(5) . . ?
C4G C4G C5G 121.7(6) 2 . ?
C1G C5G C4G 109.1(7) 2 . ?
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 1.449(3) . ?
O1 H1 0.965(7) . ?
C1 C6 1.389(3) . ?
C1 C2 1.398(3) . ?
C1 C13 1.521(3) . ?
O2 C12 1.386(3) . ?
O2 C6 1.389(3) . ?
C2 C3 1.384(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.391(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.387(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.391(4) . ?
C5 H5 0.9500 . ?
C7 C12 1.388(4) . ?
C7 C8 1.402(3) . ?
C7 C13 1.524(3) . ?
C8 C9 1.384(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.392(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.381(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.393(4) . ?
C11 H11 0.9500 . ?
C13 C14 1.528(3) . ?
C14 C19 1.390(4) . ?
C14 C15 1.393(3) . ?
C15 C16 1.389(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.388(4) . ?
C16 H16 0.9500 . ?
C17 O3 1.371(3) . ?
C17 C18 1.393(4) . ?
C18 C19 1.391(4) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
O3 C20 1.427(4) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C1G C5G 1.124(10) 2 ?
C1G C2G 1.415(11) . ?
C2G C3G 1.199(10) . ?
C3G C4G 1.434(8) . ?
C4G C4G 1.434(10) 2 ?
C4G C5G 1.456(8) . ?
C5G C1G 1.124(10) 2 ?
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 0.965(7) 1.898(7) 2.863(2) 177(4) 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
C6 C1 C2 C3 2.1(4) . . . . ?
C13 C1 C2 C3 -171.5(2) . . . . ?
C1 C2 C3 C4 -0.4(4) . . . . ?
C2 C3 C4 C5 -1.3(4) . . . . ?
C3 C4 C5 C6 1.1(4) . . . . ?
C12 O2 C6 C1 -11.5(4) . . . . ?
C12 O2 C6 C5 169.4(2) . . . . ?
C2 C1 C6 O2 178.6(2) . . . . ?
C13 C1 C6 O2 -7.7(4) . . . . ?
C2 C1 C6 C5 -2.3(4) . . . . ?
C13 C1 C6 C5 171.3(2) . . . . ?
C4 C5 C6 O2 179.8(2) . . . . ?
C4 C5 C6 C1 0.7(4) . . . . ?
C12 C7 C8 C9 -1.5(4) . . . . ?
C13 C7 C8 C9 173.6(2) . . . . ?
C7 C8 C9 C10 1.5(4) . . . . ?
C8 C9 C10 C11 -0.3(4) . . . . ?
C9 C10 C11 C12 -0.7(4) . . . . ?
C6 O2 C12 C7 13.1(4) . . . . ?
C6 O2 C12 C11 -167.7(2) . . . . ?
C8 C7 C12 O2 179.7(2) . . . . ?
C13 C7 C12 O2 4.5(4) . . . . ?
C8 C7 C12 C11 0.5(4) . . . . ?
C13 C7 C12 C11 -174.7(2) . . . . ?
C10 C11 C12 O2 -178.6(2) . . . . ?
C10 C11 C12 C7 0.6(4) . . . . ?
C6 C1 C13 O1 -96.0(3) . . . . ?
C2 C1 C13 O1 77.4(3) . . . . ?
C6 C1 C13 C7 22.5(3) . . . . ?
C2 C1 C13 C7 -164.1(2) . . . . ?
C6 C1 C13 C14 146.8(2) . . . . ?
C2 C1 C13 C14 -39.8(3) . . . . ?
C12 C7 C13 O1 97.5(3) . . . . ?
C8 C7 C13 O1 -77.5(3) . . . . ?
C12 C7 C13 C1 -21.0(3) . . . . ?
C8 C7 C13 C1 164.0(2) . . . . ?
C12 C7 C13 C14 -145.8(2) . . . . ?
C8 C7 C13 C14 39.2(3) . . . . ?
O1 C13 C14 C19 178.4(2) . . . . ?
C1 C13 C14 C19 -63.0(3) . . . . ?
C7 C13 C14 C19 60.1(3) . . . . ?
O1 C13 C14 C15 -0.5(3) . . . . ?
C1 C13 C14 C15 118.1(2) . . . . ?
C7 C13 C14 C15 -118.7(2) . . . . ?
C19 C14 C15 C16 -0.9(4) . . . . ?
C13 C14 C15 C16 178.0(2) . . . . ?
C14 C15 C16 C17 -0.4(4) . . . . ?
C15 C16 C17 O3 -179.8(2) . . . . ?
C15 C16 C17 C18 1.2(4) . . . . ?
O3 C17 C18 C19 -179.7(2) . . . . ?
C16 C17 C18 C19 -0.8(4) . . . . ?
C15 C14 C19 C18 1.3(4) . . . . ?
C13 C14 C19 C18 -177.6(2) . . . . ?
C17 C18 C19 C14 -0.5(4) . . . . ?
C16 C17 O3 C20 177.9(3) . . . . ?
C18 C17 O3 C20 -3.1(4) . . . . ?
C5G C1G C2G C3G 1.6(17) 2 . . . ?
C1G C2G C3G C4G 5.7(12) . . . . ?
C2G C3G C4G C4G -5.5(10) . . . 2 ?
C2G C3G C4G C5G 174.2(7) . . . . ?
C3G C4G C5G C1G 174.0(7) . . . 2 ?
C4G C4G C5G C1G -6.3(11) 2 . . 2 ?
