#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:05:27 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180286 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/00/7150039.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_7150039
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                97.482(2)
_cell_angle_beta                 103.946(2)
_cell_angle_gamma                109.425(3)
_cell_formula_units_Z            2
_cell_length_a                   8.3719(4)
_cell_length_b                   9.1093(5)
_cell_length_c                   12.6935(7)
_cell_measurement_reflns_used    'All data'
_cell_measurement_temperature    113(2)
_cell_volume                     862.30(8)
_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 0.953
_diffrn_measured_fraction_theta_max 0.953
_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    0.0555
_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       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3421
_diffrn_reflns_theta_full        26.54
_diffrn_reflns_theta_max         26.54
_diffrn_reflns_theta_min         2.44
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.9812
_exptl_absorpt_correction_T_min  0.9645
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.323
_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         2.167
_refine_diff_density_min         -1.350
_refine_diff_density_rms         0.337
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   2.409
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         3421
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      2.408
_refine_ls_R_factor_all          0.2241
_refine_ls_R_factor_gt           0.2028
_refine_ls_shift/su_max          0.028
_refine_ls_shift/su_mean         0.006
_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          0.5102
_refine_ls_wR_factor_ref         0.5249
_reflns_number_gt                2744
_reflns_number_total             3421
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b416331a.txt
_cod_data_source_block           c:\struct~1\a1pxy_~1\1c
_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               7150039
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
O2 O 0.0409(5) 0.4981(4) 0.3818(3) 0.0194(10) Uani 1 1 d . . .
O1 O -0.2893(5) 0.2084(4) 0.4670(3) 0.0194(10) Uani 1 1 d D . .
C7 C -0.0647(7) 0.2128(6) 0.3760(4) 0.0171(12) Uani 1 1 d . . .
C1 C -0.2755(7) 0.3447(6) 0.3171(5) 0.0189(13) Uani 1 1 d . . .
C13 C -0.2559(7) 0.2029(6) 0.3595(5) 0.0186(13) Uani 1 1 d . . .
O3 O -0.7803(6) -0.3788(5) 0.0701(4) 0.0294(12) Uani 1 1 d . . .
C11 C 0.2474(7) 0.3742(6) 0.4200(5) 0.0208(13) Uani 1 1 d . . .
H11 H 0.3392 0.4753 0.4310 0.025 Uiso 1 1 calc R . .
C10 C 0.2882(7) 0.2412(6) 0.4318(5) 0.0206(13) Uani 1 1 d . . .
H10 H 0.4088 0.2508 0.4513 0.025 Uiso 1 1 calc R . .
C6 C -0.1338(7) 0.4858(6) 0.3351(5) 0.0173(12) Uani 1 1 d . . .
C8 C -0.0181(8) 0.0811(6) 0.3870(5) 0.0200(13) Uani 1 1 d . . .
H8 H -0.1091 -0.0210 0.3745 0.024 Uiso 1 1 calc R . .
C16 C -0.6492(8) -0.2014(7) 0.2458(5) 0.0237(13) Uani 1 1 d . . .
H16 H -0.7355 -0.2727 0.2711 0.028 Uiso 1 1 calc R . .
C14 C -0.3943(7) 0.0445(6) 0.2829(5) 0.0184(13) Uani 1 1 d . . .
C12 C 0.0714(8) 0.3587(6) 0.3920(5) 0.0197(13) Uani 1 1 d . . .
C5 C -0.1488(8) 0.6246(6) 0.3076(5) 0.0232(13) Uani 1 1 d . . .
H5 H -0.0460 0.7185 0.3212 0.028 Uiso 1 1 calc R . .
C18 C -0.5189(8) -0.1362(7) 0.0989(5) 0.0238(13) Uani 1 1 d . . .
H18 H -0.5163 -0.1622 0.0246 0.029 Uiso 1 1 calc R . .
C9 C 0.1554(7) 0.0954(7) 0.4154(5) 0.0242(14) Uani 1 1 d . . .
H9 H 0.1840 0.0042 0.4239 0.029 Uiso 1 1 calc R . .
C4 C -0.3146(8) 0.6230(7) 0.2607(5) 0.0244(14) Uani 1 1 d . . .
H4 H -0.3280 0.7173 0.2430 0.029 Uiso 1 1 calc R . .
C17 C -0.6503(7) -0.2385(6) 0.1363(5) 0.0196(13) Uani 1 1 d . . .
C15 C -0.5225(7) -0.0603(7) 0.3195(5) 0.0220(13) Uani 1 1 d . . .
H15 H -0.5236 -0.0358 0.3944 0.026 Uiso 1 1 calc R . .
C2 C -0.4442(8) 0.3462(7) 0.2670(5) 0.0224(13) Uani 1 1 d . . .
H2 H -0.5468 0.2518 0.2522 0.027 Uiso 1 1 calc R . .
C19 C -0.3938(7) 0.0028(7) 0.1729(5) 0.0214(13) Uani 1 1 d . . .
H19 H -0.3049 0.0722 0.1482 0.026 Uiso 1 1 calc R . .
C3 C -0.4638(8) 0.4833(7) 0.2386(5) 0.0269(14) Uani 1 1 d . . .
H3 H -0.5788 0.4816 0.2044 0.032 Uiso 1 1 calc R . .
C20 C -0.7896(10) -0.4193(8) -0.0433(6) 0.0431(19) Uani 1 1 d . . .
H20A H -0.7990 -0.3319 -0.0787 0.065 Uiso 1 1 calc R . .
H20B H -0.8942 -0.5172 -0.0816 0.065 Uiso 1 1 calc R . .
H20C H -0.6821 -0.4369 -0.0482 0.065 Uiso 1 1 calc R . .
C2G C 0.0554(9) 0.0847(9) 0.1080(6) 0.0435(19) Uani 1 1 d . . .
H2G H 0.0957 0.1435 0.1832 0.052 Uiso 1 1 calc R . .
C3G C -0.0159(11) -0.0776(11) 0.0841(7) 0.052(2) Uani 1 1 d . . .
H3G H -0.0290 -0.1318 0.1424 0.062 Uiso 1 1 calc R . .
C1G C 0.0692(12) 0.1637(10) 0.0236(8) 0.058(2) Uani 1 1 d . . .
H1G H 0.1155 0.2773 0.0397 0.070 Uiso 1 1 calc R . .
H1 H -0.207(6) 0.304(4) 0.521(3) 0.014(14) 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
C12 O2 C6 118.5(4) . . ?
C13 O1 H1 111(3) . . ?
C12 C7 C8 117.5(5) . . ?
C12 C7 C13 120.2(5) . . ?
C8 C7 C13 121.9(5) . . ?
C6 C1 C2 115.7(5) . . ?
C6 C1 C13 122.7(5) . . ?
C2 C1 C13 121.3(5) . . ?
O1 C13 C1 108.9(4) . . ?
O1 C13 C14 105.9(4) . . ?
C1 C13 C14 111.8(4) . . ?
O1 C13 C7 108.4(4) . . ?
C1 C13 C7 109.1(4) . . ?
C14 C13 C7 112.5(4) . . ?
C17 O3 C20 118.5(5) . . ?
C10 C11 C12 119.3(5) . . ?
C10 C11 H11 120.3 . . ?
C12 C11 H11 120.4 . . ?
C9 C10 C11 120.2(5) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C1 C6 C5 124.4(5) . . ?
C1 C6 O2 121.0(5) . . ?
C5 C6 O2 114.6(5) . . ?
C9 C8 C7 121.5(5) . . ?
C9 C8 H8 119.3 . . ?
C7 C8 H8 119.2 . . ?
C17 C16 C15 120.8(5) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C15 C14 C19 118.6(5) . . ?
C15 C14 C13 121.9(5) . . ?
C19 C14 C13 119.5(5) . . ?
C11 C12 C7 121.4(5) . . ?
C11 C12 O2 115.9(5) . . ?
C7 C12 O2 122.6(5) . . ?
C4 C5 C6 118.6(5) . . ?
C4 C5 H5 120.7 . . ?
C6 C5 H5 120.7 . . ?
C19 C18 C17 118.6(5) . . ?
C19 C18 H18 120.7 . . ?
C17 C18 H18 120.7 . . ?
C8 C9 C10 120.1(5) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C5 C4 C3 120.1(5) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
O3 C17 C16 116.6(5) . . ?
O3 C17 C18 123.4(5) . . ?
C16 C17 C18 120.0(5) . . ?
C14 C15 C16 119.8(5) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C3 C2 C1 121.4(5) . . ?
C3 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?
C18 C19 C14 122.0(5) . . ?
C18 C19 H19 119.0 . . ?
C14 C19 H19 119.0 . . ?
C4 C3 C2 119.9(6) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
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 . . ?
C3G C2G C1G 120.0(7) . . ?
C3G C2G H2G 120.0 . . ?
C1G C2G H2G 120.0 . . ?
C2G C3G C1G 120.5(8) . 2 ?
C2G C3G H3G 119.8 . . ?
C1G C3G H3G 119.8 2 . ?
C3G C1G C2G 119.5(8) 2 . ?
C3G C1G H1G 120.2 2 . ?
C2G C1G H1G 120.2 . . ?
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
O2 C12 1.391(6) . ?
O2 C6 1.400(6) . ?
O1 C13 1.455(6) . ?
O1 H1 0.963(8) . ?
C7 C12 1.384(8) . ?
C7 C8 1.392(7) . ?
C7 C13 1.534(7) . ?
C1 C6 1.375(8) . ?
C1 C2 1.407(8) . ?
C1 C13 1.505(7) . ?
C13 C14 1.533(8) . ?
O3 C17 1.370(7) . ?
O3 C20 1.415(8) . ?
C11 C10 1.380(8) . ?
C11 C12 1.384(8) . ?
C11 H11 0.9500 . ?
C10 C9 1.371(8) . ?
C10 H10 0.9500 . ?
C6 C5 1.391(8) . ?
C8 C9 1.366(7) . ?
C8 H8 0.9500 . ?
C16 C17 1.384(8) . ?
C16 C15 1.398(8) . ?
C16 H16 0.9500 . ?
C14 C15 1.398(8) . ?
C14 C19 1.400(8) . ?
C5 C4 1.366(8) . ?
C5 H5 0.9500 . ?
C18 C19 1.385(8) . ?
C18 C17 1.410(8) . ?
C18 H18 0.9500 . ?
C9 H9 0.9500 . ?
C4 C3 1.393(9) . ?
C4 H4 0.9500 . ?
C15 H15 0.9500 . ?
C2 C3 1.393(8) . ?
C2 H2 0.9500 . ?
C19 H19 0.9500 . ?
C3 H3 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C2G C3G 1.357(11) . ?
C2G C1G 1.373(12) . ?
C2G H2G 0.9500 . ?
C3G C1G 1.370(12) 2 ?
C3G H3G 0.9500 . ?
C1G C3G 1.370(12) 2 ?
C1G H1G 0.9500 . ?
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 C13 O1 94.0(6) . . . . ?
C2 C1 C13 O1 -78.8(6) . . . . ?
C6 C1 C13 C14 -149.4(5) . . . . ?
C2 C1 C13 C14 37.8(7) . . . . ?
C6 C1 C13 C7 -24.2(7) . . . . ?
C2 C1 C13 C7 163.0(5) . . . . ?
C12 C7 C13 O1 -95.2(6) . . . . ?
C8 C7 C13 O1 78.1(6) . . . . ?
C12 C7 C13 C1 23.3(7) . . . . ?
C8 C7 C13 C1 -163.4(5) . . . . ?
C12 C7 C13 C14 148.1(5) . . . . ?
C8 C7 C13 C14 -38.7(7) . . . . ?
C12 C11 C10 C9 0.3(9) . . . . ?
C2 C1 C6 C5 0.2(8) . . . . ?
C13 C1 C6 C5 -172.9(5) . . . . ?
C2 C1 C6 O2 -178.4(4) . . . . ?
C13 C1 C6 O2 8.4(8) . . . . ?
C12 O2 C6 C1 11.0(7) . . . . ?
C12 O2 C6 C5 -167.8(5) . . . . ?
C12 C7 C8 C9 1.7(8) . . . . ?
C13 C7 C8 C9 -171.8(5) . . . . ?
O1 C13 C14 C15 1.6(6) . . . . ?
C1 C13 C14 C15 -116.9(5) . . . . ?
C7 C13 C14 C15 119.8(5) . . . . ?
O1 C13 C14 C19 -178.7(4) . . . . ?
C1 C13 C14 C19 62.8(6) . . . . ?
C7 C13 C14 C19 -60.4(6) . . . . ?
C10 C11 C12 C7 0.3(9) . . . . ?
C10 C11 C12 O2 179.9(5) . . . . ?
C8 C7 C12 C11 -1.2(8) . . . . ?
C13 C7 C12 C11 172.3(5) . . . . ?
C8 C7 C12 O2 179.2(5) . . . . ?
C13 C7 C12 O2 -7.2(8) . . . . ?
C6 O2 C12 C11 169.0(5) . . . . ?
C6 O2 C12 C7 -11.4(8) . . . . ?
C1 C6 C5 C4 0.8(9) . . . . ?
O2 C6 C5 C4 179.5(5) . . . . ?
C7 C8 C9 C10 -1.2(9) . . . . ?
C11 C10 C9 C8 0.2(9) . . . . ?
C6 C5 C4 C3 -1.6(9) . . . . ?
C20 O3 C17 C16 178.2(5) . . . . ?
C20 O3 C17 C18 -3.6(8) . . . . ?
C15 C16 C17 O3 -179.5(5) . . . . ?
C15 C16 C17 C18 2.2(8) . . . . ?
C19 C18 C17 O3 179.9(5) . . . . ?
C19 C18 C17 C16 -1.9(8) . . . . ?
C19 C14 C15 C16 -1.5(8) . . . . ?
C13 C14 C15 C16 178.2(5) . . . . ?
C17 C16 C15 C14 -0.5(8) . . . . ?
C6 C1 C2 C3 -0.4(8) . . . . ?
C13 C1 C2 C3 172.9(5) . . . . ?
C17 C18 C19 C14 -0.1(8) . . . . ?
C15 C14 C19 C18 1.8(8) . . . . ?
C13 C14 C19 C18 -177.9(5) . . . . ?
C5 C4 C3 C2 1.5(9) . . . . ?
C1 C2 C3 C4 -0.5(9) . . . . ?
C1G C2G C3G C1G 2.1(14) . . . 2 ?
C3G C2G C1G C3G -2.1(14) . . . 2 ?
