#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:05:27 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180286 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/00/7150038.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_7150038
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 p-xylene clathrate'
_chemical_name_systematic
;
9-(4-methoxyphenyl)-9H-xanthen-9-ol p-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                94.8930(10)
_cell_angle_beta                 96.4010(10)
_cell_angle_gamma                108.8720(10)
_cell_formula_units_Z            2
_cell_length_a                   8.3762(2)
_cell_length_b                   9.1588(3)
_cell_length_c                   12.7193(4)
_cell_measurement_reflns_used    'All data'
_cell_measurement_temperature    113(2)
_cell_volume                     909.89(5)
_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 0.979
_diffrn_measured_fraction_theta_max 0.979
_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    0.0372
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            3966
_diffrn_reflns_theta_full        27.17
_diffrn_reflns_theta_max         27.17
_diffrn_reflns_theta_min         3.25
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.9815
_exptl_absorpt_correction_T_min  0.9652
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Cuboid
_exptl_crystal_F_000             378
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.22
_refine_diff_density_max         1.140
_refine_diff_density_min         -0.863
_refine_diff_density_rms         0.278
_refine_ls_extinction_coef       0.63(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.711
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     251
_refine_ls_number_reflns         3966
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.710
_refine_ls_R_factor_all          0.1330
_refine_ls_R_factor_gt           0.1137
_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)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3574
_refine_ls_wR_factor_ref         0.3761
_reflns_number_gt                3297
_reflns_number_total             3966
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b416331a.txt
_cod_data_source_block           1b
_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               7150038
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 -0.2799(2) 0.2169(2) 0.47026(14) 0.0206(6) Uani 1 1 d D . .
O2 O 0.0736(2) 0.5129(2) 0.38612(16) 0.0237(6) Uani 1 1 d . . .
O3 O -0.6551(3) -0.3090(2) 0.09187(17) 0.0324(7) Uani 1 1 d . . .
C14 C -0.3360(3) 0.0817(3) 0.2947(2) 0.0204(7) Uani 1 1 d . . .
C7 C -0.0339(3) 0.2318(3) 0.3834(2) 0.0189(7) Uani 1 1 d . . .
C13 C -0.2187(3) 0.2270(3) 0.3681(2) 0.0193(7) Uani 1 1 d . . .
C11 C 0.2680(4) 0.3825(3) 0.4255(2) 0.0237(7) Uani 1 1 d . . .
H11 H 0.3567 0.4806 0.4357 0.028 Uiso 1 1 calc R . .
C1 C -0.2270(3) 0.3759(3) 0.3273(2) 0.0185(7) Uani 1 1 d . . .
C18 C -0.4073(4) -0.0718(3) 0.1196(2) 0.0259(7) Uani 1 1 d . . .
H18 H -0.3837 -0.0869 0.0490 0.031 Uiso 1 1 calc R . .
C12 C 0.0991(4) 0.3727(3) 0.3980(2) 0.0213(7) Uani 1 1 d . . .
C10 C 0.3051(4) 0.2483(4) 0.4377(2) 0.0256(7) Uani 1 1 d . . .
H10 H 0.4196 0.2538 0.4585 0.031 Uiso 1 1 calc R . .
C17 C -0.5454(4) -0.1766(3) 0.1537(2) 0.0247(7) Uani 1 1 d . . .
C3 C -0.3935(4) 0.5267(3) 0.2543(2) 0.0261(7) Uani 1 1 d . . .
H3 H -0.5006 0.5325 0.2256 0.031 Uiso 1 1 calc R . .
C16 C -0.5783(4) -0.1544(3) 0.2573(2) 0.0248(7) Uani 1 1 d . . .
H16 H -0.6730 -0.2273 0.2802 0.030 Uiso 1 1 calc R . .
C6 C -0.0869(4) 0.5095(3) 0.3409(2) 0.0214(7) Uani 1 1 d . . .
C2 C -0.3827(4) 0.3873(3) 0.2820(2) 0.0225(7) Uani 1 1 d . . .
H2 H -0.4823 0.2975 0.2702 0.027 Uiso 1 1 calc R . .
C15 C -0.4733(4) -0.0259(3) 0.3276(2) 0.0224(7) Uani 1 1 d . . .
H15 H -0.4960 -0.0120 0.3986 0.027 Uiso 1 1 calc R . .
C8 C 0.0090(4) 0.0978(3) 0.3933(2) 0.0227(7) Uani 1 1 d . . .
H8 H -0.0788 -0.0008 0.3816 0.027 Uiso 1 1 calc R . .
C9 C 0.1755(4) 0.1057(3) 0.4197(2) 0.0255(7) Uani 1 1 d . . .
H9 H 0.2017 0.0129 0.4256 0.031 Uiso 1 1 calc R . .
C19 C -0.3035(4) 0.0562(3) 0.1909(2) 0.0229(7) Uani 1 1 d . . .
H19 H -0.2079 0.1283 0.1681 0.027 Uiso 1 1 calc R . .
C5 C -0.0938(4) 0.6503(3) 0.3119(2) 0.0254(7) Uani 1 1 d . . .
H5 H 0.0064 0.7395 0.3221 0.031 Uiso 1 1 calc R . .
C4 C -0.2481(4) 0.6589(3) 0.2683(2) 0.0270(7) Uani 1 1 d . . .
H4 H -0.2553 0.7542 0.2478 0.032 Uiso 1 1 calc R . .
C20 C -0.6204(5) -0.3390(4) -0.0133(3) 0.0406(9) Uani 1 1 d . . .
H20A H -0.6207 -0.2515 -0.0524 0.061 Uiso 1 1 calc R . .
H20B H -0.7082 -0.4343 -0.0502 0.061 Uiso 1 1 calc R . .
H20C H -0.5084 -0.3520 -0.0097 0.061 Uiso 1 1 calc R . .
C2G C 0.1029(5) 0.0350(5) 0.0969(3) 0.0507(11) Uani 1 1 d . . .
H2G H 0.1740 0.0582 0.1640 0.061 Uiso 1 1 calc R . .
C1G C 0.0607(5) 0.1537(5) 0.0518(3) 0.0464(10) Uani 1 1 d . . .
C3G C 0.0433(5) -0.1153(5) 0.0459(3) 0.0470(10) Uani 1 1 d . . .
H3G H 0.0741 -0.1939 0.0783 0.056 Uiso 1 1 calc R . .
C4G C 0.1255(7) 0.3168(6) 0.1078(4) 0.0746(16) Uani 1 1 d . . .
H4G1 H 0.2332 0.3744 0.0843 0.112 Uiso 1 1 calc R . .
H4G2 H 0.1443 0.3149 0.1850 0.112 Uiso 1 1 calc R . .
H4G3 H 0.0413 0.3679 0.0906 0.112 Uiso 1 1 calc R . .
H1 H -0.226(4) 0.313(2) 0.517(2) 0.038(10) Uiso 1 1 d 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 111(2) . . ?
C12 O2 C6 118.4(2) . . ?
C17 O3 C20 116.8(3) . . ?
C15 C14 C19 118.5(3) . . ?
C15 C14 C13 122.5(3) . . ?
C19 C14 C13 119.0(2) . . ?
C12 C7 C8 117.2(3) . . ?
C12 C7 C13 120.6(2) . . ?
C8 C7 C13 122.0(2) . . ?
O1 C13 C1 109.0(2) . . ?
O1 C13 C7 108.7(2) . . ?
C1 C13 C7 109.2(2) . . ?
O1 C13 C14 105.9(2) . . ?
C1 C13 C14 112.0(2) . . ?
C7 C13 C14 111.9(2) . . ?
C10 C11 C12 119.2(3) . . ?
C10 C11 H11 120.4 . . ?
C12 C11 H11 120.4 . . ?
C6 C1 C2 116.6(3) . . ?
C6 C1 C13 122.1(2) . . ?
C2 C1 C13 121.1(2) . . ?
C17 C18 C19 118.7(3) . . ?
C17 C18 H18 120.6 . . ?
C19 C18 H18 120.6 . . ?
O2 C12 C7 122.7(2) . . ?
O2 C12 C11 115.3(2) . . ?
C7 C12 C11 122.0(3) . . ?
C11 C10 C9 120.0(3) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
O3 C17 C18 124.3(3) . . ?
O3 C17 C16 115.3(3) . . ?
C18 C17 C16 120.3(3) . . ?
C2 C3 C4 120.4(3) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C17 C16 C15 120.3(3) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C1 C6 C5 123.2(3) . . ?
C1 C6 O2 121.8(2) . . ?
C5 C6 O2 114.9(3) . . ?
C3 C2 C1 121.2(3) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
C14 C15 C16 120.3(3) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C9 C8 C7 121.5(3) . . ?
C9 C8 H8 119.3 . . ?
C7 C8 H8 119.3 . . ?
C8 C9 C10 120.1(3) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C18 C19 C14 121.8(3) . . ?
C18 C19 H19 119.1 . . ?
C14 C19 H19 119.1 . . ?
C4 C5 C6 119.1(3) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
C5 C4 C3 119.5(3) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
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 . . ?
C3G C2G C1G 121.2(4) . . ?
C3G C2G H2G 119.4 . . ?
C1G C2G H2G 119.4 . . ?
C3G C1G C2G 117.7(4) 2 . ?
C3G C1G C4G 121.3(4) 2 . ?
C2G C1G C4G 121.0(4) . . ?
C2G C3G C1G 121.1(4) . 2 ?
C2G C3G H3G 119.5 . . ?
C1G C3G H3G 119.5 2 . ?
C1G C4G H4G1 109.5 . . ?
C1G C4G H4G2 109.5 . . ?
H4G1 C4G H4G2 109.5 . . ?
C1G C4G H4G3 109.5 . . ?
H4G1 C4G H4G3 109.5 . . ?
H4G2 C4G H4G3 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 1.448(3) . ?
O1 H1 0.959(8) . ?
O2 C12 1.385(3) . ?
O2 C6 1.392(3) . ?
O3 C17 1.375(4) . ?
O3 C20 1.423(4) . ?
C14 C15 1.383(4) . ?
C14 C19 1.393(4) . ?
C14 C13 1.532(4) . ?
C7 C12 1.387(4) . ?
C7 C8 1.397(4) . ?
C7 C13 1.524(4) . ?
C13 C1 1.520(4) . ?
C11 C10 1.379(4) . ?
C11 C12 1.390(4) . ?
C11 H11 0.9500 . ?
C1 C6 1.377(4) . ?
C1 C2 1.405(4) . ?
C18 C17 1.382(4) . ?
C18 C19 1.391(4) . ?
C18 H18 0.9500 . ?
C10 C9 1.383(4) . ?
C10 H10 0.9500 . ?
C17 C16 1.387(4) . ?
C3 C2 1.381(4) . ?
C3 C4 1.394(4) . ?
C3 H3 0.9500 . ?
C16 C15 1.391(4) . ?
C16 H16 0.9500 . ?
C6 C5 1.388(4) . ?
C2 H2 0.9500 . ?
C15 H15 0.9500 . ?
C8 C9 1.375(4) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C19 H19 0.9500 . ?
C5 C4 1.377(4) . ?
C5 H5 0.9500 . ?
C4 H4 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C2G C3G 1.377(6) . ?
C2G C1G 1.395(6) . ?
C2G H2G 0.9500 . ?
C1G C3G 1.383(6) 2 ?
C1G C4G 1.497(6) . ?
C3G C1G 1.383(6) 2 ?
C3G H3G 0.9500 . ?
C4G H4G1 0.9800 . ?
C4G H4G2 0.9800 . ?
C4G H4G3 0.9800 . ?
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 0.959(8) 1.925(8) 2.865(3) 166(3) 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
C12 C7 C13 O1 -95.8(3) . . . . ?
C8 C7 C13 O1 78.1(3) . . . . ?
C12 C7 C13 C1 22.9(3) . . . . ?
C8 C7 C13 C1 -163.1(2) . . . . ?
C12 C7 C13 C14 147.5(3) . . . . ?
C8 C7 C13 C14 -38.5(3) . . . . ?
C15 C14 C13 O1 2.4(3) . . . . ?
C19 C14 C13 O1 -177.5(2) . . . . ?
C15 C14 C13 C1 -116.3(3) . . . . ?
C19 C14 C13 C1 63.8(3) . . . . ?
C15 C14 C13 C7 120.7(3) . . . . ?
C19 C14 C13 C7 -59.2(3) . . . . ?
O1 C13 C1 C6 97.3(3) . . . . ?
C7 C13 C1 C6 -21.4(3) . . . . ?
C14 C13 C1 C6 -145.9(3) . . . . ?
O1 C13 C1 C2 -77.0(3) . . . . ?
C7 C13 C1 C2 164.4(2) . . . . ?
C14 C13 C1 C2 39.8(3) . . . . ?
C6 O2 C12 C7 -10.9(4) . . . . ?
C6 O2 C12 C11 169.0(2) . . . . ?
C8 C7 C12 O2 177.4(2) . . . . ?
C13 C7 C12 O2 -8.4(4) . . . . ?
C8 C7 C12 C11 -2.5(4) . . . . ?
C13 C7 C12 C11 171.7(3) . . . . ?
C10 C11 C12 O2 -179.3(2) . . . . ?
C10 C11 C12 C7 0.6(5) . . . . ?
C12 C11 C10 C9 1.8(4) . . . . ?
C20 O3 C17 C18 0.9(4) . . . . ?
C20 O3 C17 C16 -177.2(3) . . . . ?
C19 C18 C17 O3 -178.6(2) . . . . ?
C19 C18 C17 C16 -0.5(4) . . . . ?
O3 C17 C16 C15 178.7(2) . . . . ?
C18 C17 C16 C15 0.4(4) . . . . ?
C2 C1 C6 C5 -0.3(4) . . . . ?
C13 C1 C6 C5 -174.8(3) . . . . ?
C2 C1 C6 O2 179.3(2) . . . . ?
C13 C1 C6 O2 4.7(4) . . . . ?
C12 O2 C6 C1 12.8(4) . . . . ?
C12 O2 C6 C5 -167.6(2) . . . . ?
C4 C3 C2 C1 1.7(4) . . . . ?
C6 C1 C2 C3 -0.9(4) . . . . ?
C13 C1 C2 C3 173.7(3) . . . . ?
C19 C14 C15 C16 -1.5(4) . . . . ?
C13 C14 C15 C16 178.6(2) . . . . ?
C17 C16 C15 C14 0.6(4) . . . . ?
C12 C7 C8 C9 2.0(4) . . . . ?
C13 C7 C8 C9 -172.1(3) . . . . ?
C7 C8 C9 C10 0.3(5) . . . . ?
C11 C10 C9 C8 -2.3(5) . . . . ?
C17 C18 C19 C14 -0.5(4) . . . . ?
C15 C14 C19 C18 1.5(4) . . . . ?
C13 C14 C19 C18 -178.7(2) . . . . ?
C1 C6 C5 C4 0.7(5) . . . . ?
O2 C6 C5 C4 -178.9(3) . . . . ?
C6 C5 C4 C3 0.1(5) . . . . ?
C2 C3 C4 C5 -1.3(5) . . . . ?
C3G C2G C1G C3G 0.1(6) . . . 2 ?
C3G C2G C1G C4G 179.8(4) . . . . ?
C1G C2G C3G C1G -0.1(6) . . . 2 ?
