#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:05:27 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180286 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/00/7150037.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_7150037
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                94.8100(10)
_cell_angle_beta                 96.3740(10)
_cell_angle_gamma                108.9480(10)
_cell_formula_units_Z            2
_cell_length_a                   8.3773(2)
_cell_length_b                   9.1657(3)
_cell_length_c                   12.7261(4)
_cell_measurement_reflns_used    'All data'
_cell_measurement_temperature    113(2)
_cell_volume                     910.99(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    'ZORTEP (Zsolnai & Pritzkow, 1994)'
_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 0.970
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'Nonius Kappa CCD diffractometer'
_diffrn_measurement_method       '1.2° 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    0.0338
_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       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            3932
_diffrn_reflns_theta_full        27.16
_diffrn_reflns_theta_max         27.16
_diffrn_reflns_theta_min         3.25
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.9816
_exptl_absorpt_correction_T_min  0.9652
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rectangle
_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         0.870
_refine_diff_density_min         -1.037
_refine_diff_density_rms         0.318
_refine_ls_extinction_coef       N/A
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.165
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         3932
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.164
_refine_ls_R_factor_all          0.0879
_refine_ls_R_factor_gt           0.0567
_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)+(0.1429P)²+0.0253P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1596
_refine_ls_wR_factor_ref         0.2074
_reflns_number_gt                3140
_reflns_number_total             3932
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b416331a.txt
_cod_data_source_block           1a
_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               7150037
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 -0.28014(14) 0.21733(13) 0.47030(8) 0.0177(3) Uani 1 1 d D . .
H1 H -0.213(3) 0.3092(17) 0.5168(15) 0.050(7) Uiso 1 1 d D . .
O2 O 0.07446(14) 0.51309(13) 0.38629(10) 0.0207(3) Uani 1 1 d . . .
O3 O -0.65430(17) -0.30850(14) 0.09196(10) 0.0282(3) Uani 1 1 d . . .
C1 C -0.03428(19) 0.23238(19) 0.38368(12) 0.0160(4) Uani 1 1 d . . .
C2 C 0.0074(2) 0.0980(2) 0.39341(13) 0.0196(4) Uani 1 1 d . . .
H2 H -0.0809 -0.0003 0.3816 0.024 Uiso 1 1 calc R . .
C3 C 0.1750(2) 0.1052(2) 0.41997(14) 0.0221(4) Uani 1 1 d . . .
H3 H 0.2006 0.0123 0.4261 0.026 Uiso 1 1 calc R . .
C4 C 0.3055(2) 0.2484(2) 0.43759(13) 0.0219(4) Uani 1 1 d . . .
H4 H 0.4200 0.2539 0.4581 0.026 Uiso 1 1 calc R . .
C5 C 0.2683(2) 0.3824(2) 0.42529(14) 0.0212(4) Uani 1 1 d . . .
H5 H 0.3573 0.4803 0.4352 0.025 Uiso 1 1 calc R . .
C6 C 0.0994(2) 0.37297(19) 0.39814(13) 0.0171(4) Uani 1 1 d . . .
C7 C -0.22810(19) 0.37609(18) 0.32715(12) 0.0156(4) Uani 1 1 d . . .
C8 C -0.3823(2) 0.3884(2) 0.28178(13) 0.0199(4) Uani 1 1 d . . .
H8 H -0.4821 0.2988 0.2699 0.024 Uiso 1 1 calc R . .
C9 C -0.3929(2) 0.5278(2) 0.25379(14) 0.0227(4) Uani 1 1 d . . .
H9 H -0.4997 0.5338 0.2246 0.027 Uiso 1 1 calc R . .
C10 C -0.2468(2) 0.6595(2) 0.26849(14) 0.0236(4) Uani 1 1 d . . .
H10 H -0.2534 0.7554 0.2490 0.028 Uiso 1 1 calc R . .
C11 C -0.0930(2) 0.6497(2) 0.31145(14) 0.0216(4) Uani 1 1 d . . .
H11 H 0.0076 0.7386 0.3208 0.026 Uiso 1 1 calc R . .
C12 C -0.0854(2) 0.50957(19) 0.34108(13) 0.0176(4) Uani 1 1 d . . .
C13 C -0.21902(19) 0.22715(18) 0.36839(12) 0.0158(4) Uani 1 1 d . . .
C14 C -0.3356(2) 0.08271(18) 0.29473(13) 0.0164(4) Uani 1 1 d . . .
C15 C -0.3031(2) 0.05736(19) 0.19109(13) 0.0200(4) Uani 1 1 d . . .
H15 H -0.2076 0.1296 0.1683 0.024 Uiso 1 1 calc R . .
C16 C -0.4062(2) -0.0705(2) 0.12010(13) 0.0212(4) Uani 1 1 d . . .
H16 H -0.3824 -0.0852 0.0495 0.025 Uiso 1 1 calc R . .
C17 C -0.5447(2) -0.17617(19) 0.15406(14) 0.0208(4) Uani 1 1 d . . .
C18 C -0.5780(2) -0.1538(2) 0.25742(14) 0.0218(4) Uani 1 1 d . . .
H18 H -0.6728 -0.2268 0.2803 0.026 Uiso 1 1 calc R . .
C19 C -0.4738(2) -0.02530(19) 0.32775(13) 0.0192(4) Uani 1 1 d . . .
H19 H -0.4972 -0.0113 0.3985 0.023 Uiso 1 1 calc R . .
C20 C -0.6195(3) -0.3388(2) -0.01277(15) 0.0355(5) Uani 1 1 d . . .
H20A H -0.6181 -0.2509 -0.0519 0.053 Uiso 1 1 calc R . .
H20B H -0.7082 -0.4334 -0.0497 0.053 Uiso 1 1 calc R . .
H20C H -0.5082 -0.3532 -0.0090 0.053 Uiso 1 1 calc R . .
C1G C 0.0620(3) 0.1532(3) 0.05281(17) 0.0382(5) Uani 1 1 d . . .
C2G C 0.1032(3) 0.0346(3) 0.09674(16) 0.0408(6) Uani 1 1 d . . .
H2G H 0.1745 0.0570 0.1637 0.049 Uiso 1 1 calc R . .
C3G C 0.0426(3) -0.1156(3) 0.04517(18) 0.0402(6) Uani 1 1 d . . .
H3G H 0.0729 -0.1947 0.0772 0.048 Uiso 1 1 calc R . .
C4G C 0.1273(4) 0.3170(3) 0.1095(2) 0.0696(9) Uani 1 1 d . . .
H4G1 H 0.2333 0.3758 0.0844 0.104 Uiso 1 1 calc R . .
H4G2 H 0.1495 0.3147 0.1864 0.104 Uiso 1 1 calc R . .
H4G3 H 0.0417 0.3671 0.0944 0.104 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 108.73(12) . . ?
O1 C13 C7 108.83(12) . . ?
O1 C13 C14 106.34(12) . . ?
O2 C6 C1 122.56(14) . . ?
O2 C6 C5 115.38(14) . . ?
O2 C12 C7 122.58(14) . . ?
O2 C12 C11 115.21(14) . . ?
O3 C17 C16 124.29(16) . . ?
O3 C17 C18 115.57(15) . . ?
O3 C20 H20A 109.5 . . ?
O3 C20 H20B 109.5 . . ?
O3 C20 H20C 109.5 . . ?
C1 C6 C5 122.07(15) . . ?
C1 C13 C7 109.31(13) . . ?
C1 C13 C14 111.93(13) . . ?
C1 C2 H2 119.3 . . ?
C2 C1 C13 121.48(14) . . ?
C2 C3 C4 119.88(16) . . ?
C2 C3 H3 120.1 . . ?
C3 C2 C1 121.39(16) . . ?
C3 C2 H2 119.3 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 119.42(15) . . ?
C4 C5 H5 120.3 . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 119.88(15) . . ?
C5 C4 H4 120.1 . . ?
C6 O2 C12 118.20(12) . . ?
C6 C5 H5 120.3 . . ?
C6 C1 C2 117.28(14) . . ?
C6 C1 C13 120.99(14) . . ?
C7 C13 C14 111.58(12) . . ?
C7 C8 H8 119.2 . . ?
C7 C12 C11 122.21(15) . . ?
C8 C7 C13 121.76(14) . . ?
C8 C9 C10 119.89(15) . . ?
C8 C9 H9 120.1 . . ?
C9 C8 C7 121.61(15) . . ?
C9 C8 H8 119.2 . . ?
C9 C10 H10 120.2 . . ?
C10 C9 H9 120.1 . . ?
C10 C11 C12 119.71(16) . . ?
C10 C11 H11 120.1 . . ?
C11 C10 C9 119.59(16) . . ?
C11 C10 H10 120.2 . . ?
C12 C7 C8 116.97(15) . . ?
C12 C7 C13 121.06(14) . . ?
C12 C11 H11 120.1 . . ?
C13 O1 H1 108.0(15) . . ?
C14 C19 C18 120.15(16) . . ?
C14 C15 H15 119.1 . . ?
C14 C19 H19 119.9 . . ?
C15 C14 C13 119.35(14) . . ?
C15 C16 H16 120.6 . . ?
C16 C17 C18 120.13(15) . . ?
C16 C15 C14 121.88(15) . . ?
C16 C15 H15 119.1 . . ?
C17 O3 C20 117.12(15) . . ?
C17 C16 C15 118.83(16) . . ?
C17 C16 H16 120.6 . . ?
C17 C18 C19 120.51(16) . . ?
C17 C18 H18 119.7 . . ?
C18 C19 H19 119.9 . . ?
C19 C14 C15 118.50(15) . . ?
C19 C14 C13 122.14(15) . . ?
C19 C18 H18 119.7 . . ?
C1G C2G H2G 119.4 . . ?
C1G C3G H3G 119.4 2 . ?
C1G C4G H4G1 109.5 . . ?
C1G C4G H4G2 109.5 . . ?
C1G C4G H4G3 109.5 . . ?
C2G C1G C3G 117.6(2) . 2 ?
C2G C1G C4G 121.2(2) . . ?
C2G C3G C1G 121.1(2) . 2 ?
C2G C3G H3G 119.4 . . ?
C3G C1G C4G 121.1(2) 2 . ?
C3G C2G C1G 121.3(2) . . ?
C3G C2G H2G 119.4 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
H4G1 C4G H4G2 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 1.4454(18) . ?
O1 H1 0.954(7) . ?
O2 C6 1.3839(19) . ?
O2 C12 1.3866(19) . ?
O3 C17 1.376(2) . ?
O3 C20 1.420(2) . ?
C1 C2 1.396(2) . ?
C2 C3 1.385(2) . ?
C2 H2 0.9500 . ?
C3 H3 0.9500 . ?
C4 C3 1.391(2) . ?
C4 H4 0.9500 . ?
C5 C4 1.378(2) . ?
C5 C6 1.392(2) . ?
C5 H5 0.9500 . ?
C6 C1 1.388(2) . ?
C7 C12 1.387(2) . ?
C7 C8 1.398(2) . ?
C8 C9 1.382(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.393(2) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C10 1.376(2) . ?
C11 C12 1.388(2) . ?
C11 H11 0.9500 . ?
C13 C1 1.523(2) . ?
C13 C7 1.524(2) . ?
C14 C19 1.390(2) . ?
C14 C15 1.392(2) . ?
C14 C13 1.528(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.386(2) . ?
C16 C15 1.388(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.387(3) . ?
C18 H18 0.9500 . ?
C19 C18 1.390(2) . ?
C19 H19 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C1G C3G 1.390(3) 2 ?
C1G C4G 1.507(3) . ?
C2G C3G 1.380(3) . ?
C2G C1G 1.384(3) . ?
C2G H2G 0.9500 . ?
C3G C1G 1.390(3) 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 0.954(7) 1.908(7) 2.8610(15) 177(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 C6 -95.69(17) . . . . ?
O1 C13 C7 C8 -77.10(18) . . . . ?
O1 C13 C1 C2 78.40(17) . . . . ?
O1 C13 C7 C12 97.55(16) . . . . ?
O2 C6 C1 C13 -8.3(2) . . . . ?
O2 C6 C1 C2 177.35(14) . . . . ?
O3 C17 C18 C19 178.96(14) . . . . ?
C1 C13 C7 C8 164.29(14) . . . . ?
C1 C13 C7 C12 -21.1(2) . . . . ?
C1 C2 C3 C4 0.0(3) . . . . ?
C4 C5 C6 O2 -179.28(14) . . . . ?
C4 C5 C6 C1 0.5(3) . . . . ?
C5 C6 C1 C13 171.91(15) . . . . ?
C5 C6 C1 C2 -2.4(2) . . . . ?
C5 C4 C3 C2 -2.0(3) . . . . ?
C6 C1 C2 C3 2.1(2) . . . . ?
C6 O2 C12 C7 13.2(2) . . . . ?
C6 O2 C12 C11 -167.36(14) . . . . ?
C6 C5 C4 C3 1.8(3) . . . . ?
C7 C13 C1 C6 23.0(2) . . . . ?
C7 C13 C1 C2 -162.92(14) . . . . ?
C7 C8 C9 C10 1.4(3) . . . . ?
C8 C7 C12 O2 179.23(14) . . . . ?
C8 C7 C12 C11 -0.2(2) . . . . ?
C8 C9 C10 C11 -0.4(3) . . . . ?
C10 C11 C12 O2 -178.24(15) . . . . ?
C10 C11 C12 C7 1.2(3) . . . . ?
C12 C11 C10 C9 -0.9(3) . . . . ?
C12 O2 C6 C1 -11.1(2) . . . . ?
C12 O2 C6 C5 168.64(14) . . . . ?
C12 C7 C8 C9 -1.1(2) . . . . ?
C13 C7 C8 C9 173.72(15) . . . . ?
C13 C14 C19 C18 178.98(14) . . . . ?
C13 C7 C12 O2 4.3(2) . . . . ?
C13 C14 C15 C16 -178.93(14) . . . . ?
C13 C1 C2 C3 -172.17(15) . . . . ?
C13 C7 C12 C11 -175.11(15) . . . . ?
C14 C19 C18 C17 0.4(3) . . . . ?
C14 C13 C1 C6 147.13(15) . . . . ?
C14 C13 C1 C2 -38.8(2) . . . . ?
C14 C13 C7 C12 -145.41(15) . . . . ?
C14 C13 C7 C8 39.9(2) . . . . ?
C15 C14 C13 C7 63.91(19) . . . . ?
C15 C14 C13 C1 -58.95(19) . . . . ?
C15 C14 C13 O1 -177.55(13) . . . . ?
C15 C16 C17 O3 -178.81(15) . . . . ?
C15 C16 C17 C18 -0.2(3) . . . . ?
C15 C14 C19 C18 -1.1(2) . . . . ?
C16 C17 C18 C19 0.2(3) . . . . ?
C17 C16 C15 C14 -0.5(3) . . . . ?
C19 C14 C15 C16 1.2(2) . . . . ?
C19 C14 C13 O1 2.3(2) . . . . ?
C19 C14 C13 C1 120.95(16) . . . . ?
C19 C14 C13 C7 -116.19(16) . . . . ?
C20 O3 C17 C16 1.4(3) . . . . ?
C20 O3 C17 C18 -177.24(15) . . . . ?
C20 O3 C17 C16 1.4(3) . . . . ?
C20 O3 C17 C18 -177.24(15) . . . . ?
C1G C2G C3G C1G 0.0(3) . . . 2 ?
C3G C2G C1G C3G 0.0(3) . . . 2 ?
C3G C2G C1G C4G 179.63(19) . . . . ?
