#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:05:27 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180286 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/00/7150041.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_7150041
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                97.5410(10)
_cell_angle_beta                 104.0530(10)
_cell_angle_gamma                109.4050(10)
_cell_formula_units_Z            2
_cell_length_a                   8.37570(10)
_cell_length_b                   9.10040(10)
_cell_length_c                   12.6928(2)
_cell_measurement_reflns_used    'All data'
_cell_measurement_temperature    113(2)
_cell_volume                     861.14(2)
_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 0.990
_diffrn_measured_fraction_theta_max 0.990
_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  0.0139
_diffrn_reflns_av_sigmaI/netI    0.0267
_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            7360
_diffrn_reflns_theta_full        27.54
_diffrn_reflns_theta_max         27.54
_diffrn_reflns_theta_min         3.48
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.9744
_exptl_absorpt_correction_T_min  0.9661
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cuboid
_exptl_crystal_F_000             362
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         3932
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0396
_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)+(0.0560P)²+0.2666P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1032
_refine_ls_wR_factor_ref         0.1087
_reflns_number_gt                3323
_reflns_number_total             3932
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b416331a.txt
_cod_data_source_block           c:\struct~1\a1benzen\a1benzen
_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_cell_volume        861.135(19)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7150041
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 -0.28900(10) 0.20799(9) 0.46642(6) 0.01629(18) Uani 1 1 d D . .
H1 H -0.2041(18) 0.3060(13) 0.5149(12) 0.043(5) Uiso 1 1 d D . .
O2 O 0.04079(10) 0.49768(9) 0.38176(7) 0.01771(19) Uani 1 1 d . . .
H2 H -0.1110 -0.0222 0.3757 0.021 Uiso 1 1 calc R . .
O3 O -0.78200(11) -0.37959(10) 0.07044(7) 0.0236(2) Uani 1 1 d . . .
H3 H 0.1847 0.0027 0.4231 0.023 Uiso 1 1 calc R . .
C1 C -0.06645(14) 0.21222(13) 0.37570(9) 0.0144(2) Uani 1 1 d . . .
C2 C -0.02002(15) 0.07973(14) 0.38725(9) 0.0175(2) Uani 1 1 d . . .
C3 C 0.15589(16) 0.09406(14) 0.41518(10) 0.0191(2) Uani 1 1 d . . .
C3G C -0.0153(2) -0.0784(2) 0.08491(13) 0.0405(4) Uani 1 1 d . . .
C4 C 0.29037(15) 0.24250(14) 0.43158(10) 0.0195(2) Uani 1 1 d . . .
H4 H 0.4111 0.2528 0.4519 0.023 Uiso 1 1 calc R . .
C5 C 0.24830(15) 0.37493(14) 0.41839(10) 0.0186(2) Uani 1 1 d . . .
H5 H 0.3392 0.4761 0.4279 0.022 Uiso 1 1 calc R . .
C6 C 0.07082(15) 0.35799(13) 0.39101(9) 0.0150(2) Uani 1 1 d . . .
C7 C -0.27835(15) 0.34444(13) 0.31604(9) 0.0151(2) Uani 1 1 d . . .
C8 C -0.44643(15) 0.34484(14) 0.26474(10) 0.0193(2) Uani 1 1 d . . .
H8 H -0.5487 0.2493 0.2479 0.023 Uiso 1 1 calc R . .
C9 C -0.46628(16) 0.48196(15) 0.23819(10) 0.0225(3) Uani 1 1 d . . .
H9 H -0.5814 0.4802 0.2042 0.027 Uiso 1 1 calc R . .
C10 C -0.31717(17) 0.62240(14) 0.26143(10) 0.0218(3) Uani 1 1 d . . .
H10 H -0.3308 0.7171 0.2446 0.026 Uiso 1 1 calc R . .
C11 C -0.14970(16) 0.62405(14) 0.30885(10) 0.0190(2) Uani 1 1 d . . .
H11 H -0.0474 0.7189 0.3236 0.023 Uiso 1 1 calc R . .
C12 C -0.13247(15) 0.48493(13) 0.33487(9) 0.0156(2) Uani 1 1 d . . .
C13 C -0.25639(14) 0.20148(13) 0.35915(9) 0.0140(2) Uani 1 1 d . . .
C14 C -0.39349(14) 0.04324(13) 0.28271(9) 0.0142(2) Uani 1 1 d . . .
C15 C -0.52224(15) -0.06129(14) 0.31854(9) 0.0171(2) Uani 1 1 d . . .
H15 H -0.5228 -0.0365 0.3935 0.021 Uiso 1 1 calc R . .
C16 C -0.64949(15) -0.20121(14) 0.24551(10) 0.0187(2) Uani 1 1 d . . .
H16 H -0.7365 -0.2717 0.2708 0.022 Uiso 1 1 calc R . .
C17 C -0.65040(15) -0.23875(13) 0.13581(9) 0.0175(2) Uani 1 1 d . . .
C18 C -0.52092(16) -0.13737(14) 0.09903(9) 0.0190(2) Uani 1 1 d . . .
H18 H -0.5193 -0.1633 0.0244 0.023 Uiso 1 1 calc R . .
C19 C -0.39380(15) 0.00256(13) 0.17325(9) 0.0173(2) Uani 1 1 d . . .
H19 H -0.3052 0.0719 0.1484 0.021 Uiso 1 1 calc R . .
C20 C -0.7926(2) -0.41786(18) -0.04413(11) 0.0360(3) Uani 1 1 d . . .
H20A H -0.8045 -0.3302 -0.0785 0.054 Uiso 1 1 calc R . .
H20B H -0.8962 -0.5166 -0.0828 0.054 Uiso 1 1 calc R . .
H20C H -0.6843 -0.4332 -0.0500 0.054 Uiso 1 1 calc R . .
C1G C 0.0702(2) 0.16483(19) 0.02426(14) 0.0420(4) Uani 1 1 d . . .
H1G H 0.1181 0.2786 0.0406 0.050 Uiso 1 1 calc R . .
C2G C 0.05545(19) 0.08652(19) 0.10915(12) 0.0348(3) Uani 1 1 d . . .
H2G H 0.0939 0.1459 0.1842 0.042 Uiso 1 1 calc R . .
H3G H -0.0265 -0.1329 0.1433 0.049 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 108.41(8) . . ?
O1 C13 C14 106.30(8) . . ?
O1 C13 C7 108.46(8) . . ?
O2 C12 C11 115.13(10) . . ?
O2 C12 C7 122.57(10) . . ?
O2 C6 C5 115.27(10) . . ?
O3 C17 C16 115.77(10) . . ?
O3 C17 C18 124.23(10) . . ?
O3 C20 H20A 109.5 . . ?
O3 C20 H20B 109.5 . . ?
O3 C20 H20C 109.5 . . ?
C1 C13 C14 112.48(9) . . ?
C1 C13 C7 109.40(9) . . ?
C1 C2 H2 119.3 . . ?
C1 C6 C5 122.38(10) . . ?
C1 C6 O2 122.33(10) . . ?
C2 C1 C13 121.48(10) . . ?
C2 C3 C4 119.90(10) . . ?
C2 C3 H3 120.0 . . ?
C3 C2 C1 121.36(11) . . ?
C3 C2 H2 119.3 . . ?
C3 C4 H4 120.0 . . ?
C4 C3 H3 120.0 . . ?
C4 C5 C6 119.07(11) . . ?
C4 C5 H5 120.5 . . ?
C5 C4 C3 120.05(10) . . ?
C5 C4 H4 120.0 . . ?
C6 C1 C13 121.00(9) . . ?
C6 C1 C2 117.22(10) . . ?
C6 C5 H5 120.5 . . ?
C7 C12 C11 122.30(10) . . ?
C7 C13 C14 111.62(9) . . ?
C7 C8 H8 119.4 . . ?
C8 C7 C13 121.75(10) . . ?
C8 C9 C10 119.92(11) . . ?
C8 C9 H9 120.0 . . ?
C9 C10 H10 120.0 . . ?
C9 C8 C7 121.24(11) . . ?
C9 C8 H8 119.4 . . ?
C10 C11 C12 119.18(11) . . ?
C10 C11 H11 120.4 . . ?
C10 C9 H9 120.0 . . ?
C11 C10 C9 120.03(11) . . ?
C11 C10 H10 120.0 . . ?
C12 C11 H11 120.4 . . ?
C12 C7 C13 120.77(10) . . ?
C12 C7 C8 117.26(10) . . ?
C12 O2 C6 118.19(9) . . ?
C13 O1 H1 107.1(10) . . ?
C14 C15 H15 119.8 . . ?
C14 C19 C18 121.58(10) . . ?
C14 C19 H19 119.2 . . ?
C15 C14 C13 121.95(10) . . ?
C15 C16 H16 119.8 . . ?
C16 C15 C14 120.47(10) . . ?
C16 C15 H15 119.8 . . ?
C16 C17 C18 119.99(10) . . ?
C17 C16 C15 120.38(11) . . ?
C17 C16 H16 119.8 . . ?
C17 C18 C19 119.02(10) . . ?
C17 C18 H18 120.5 . . ?
C17 O3 C20 117.27(9) . . ?
C18 C19 H19 119.2 . . ?
C19 C14 C13 119.51(10) . . ?
C19 C14 C15 118.53(10) . . ?
C19 C18 H18 120.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C1G C2G C3G 119.70(14) . . ?
C1G C2G H2G 120.2 . . ?
C1G C3G H3G 119.9 2 . ?
C2G C1G C3G 120.17(15) . 2 ?
C2G C1G H1G 119.9 . . ?
C2G C3G C1G 120.13(14) . 2 ?
C2G C3G H3G 119.9 . . ?
C3G C1G H1G 119.9 2 . ?
C3G C2G H2G 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
O1 C13 1.4498(12) . ?
O1 H1 0.950(7) . ?
O2 C12 1.3871(13) . ?
O2 C6 1.3894(13) . ?
O3 C17 1.3726(13) . ?
O3 C20 1.4241(15) . ?
C1 C2 1.3988(15) . ?
C1 C6 1.3892(16) . ?
C2 H2 0.9500 . ?
C3 C2 1.3856(16) . ?
C3 C4 1.3922(17) . ?
C3 H3 0.9500 . ?
C4 H4 0.9500 . ?
C5 C4 1.3825(16) . ?
C5 H5 0.9500 . ?
C6 C5 1.3917(16) . ?
C7 C12 1.3873(16) . ?
C7 C8 1.4017(16) . ?
C8 C9 1.3854(16) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C9 1.3934(18) . ?
C10 H10 0.9500 . ?
C11 C10 1.3797(17) . ?
C11 C12 1.3931(15) . ?
C11 H11 0.9500 . ?
C13 C1 1.5211(15) . ?
C13 C7 1.5241(14) . ?
C14 C13 1.5255(15) . ?
C14 C15 1.3945(15) . ?
C14 C19 1.3893(15) . ?
C15 H15 0.9500 . ?
C16 C15 1.3875(16) . ?
C16 C17 1.3870(16) . ?
C16 H16 0.9500 . ?
C17 C18 1.3926(16) . ?
C18 H18 0.9500 . ?
C19 C18 1.3928(16) . ?
C19 H19 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C1G C3G 1.384(2) 2 ?
C1G H1G 0.9500 . ?
C2G C1G 1.375(2) . ?
C2G C3G 1.377(2) . ?
C2G H2G 0.9500 . ?
C3G C1G 1.384(2) 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 0.950(7) 1.916(7) 2.8652(11) 176.8(15) 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 78.23(12) . . . . ?
O1 C13 C1 C6 -95.30(11) . . . . ?
O1 C13 C7 C12 94.65(11) . . . . ?
O1 C13 C7 C8 -79.75(12) . . . . ?
O2 C6 C5 C4 178.65(10) . . . . ?
O3 C17 C18 C19 -179.94(10) . . . . ?
C1 C13 C7 C12 -23.42(14) . . . . ?
C1 C13 C7 C8 162.18(10) . . . . ?
C1 C6 C5 C4 -0.40(17) . . . . ?
C2 C1 C6 C5 -0.95(16) . . . . ?
C2 C1 C6 O2 -179.93(9) . . . . ?
C2 C3 C4 C5 -0.97(17) . . . . ?
C4 C3 C2 C1 -0.43(17) . . . . ?
C6 C1 C2 C3 1.36(16) . . . . ?
C6 C5 C4 C3 1.37(17) . . . . ?
C6 O2 C12 C11 -168.46(9) . . . . ?
C6 O2 C12 C7 12.08(15) . . . . ?
C7 C13 C1 C2 -163.67(10) . . . . ?
C7 C13 C1 C6 22.81(14) . . . . ?
C7 C8 C9 C10 0.69(18) . . . . ?
C8 C7 C12 C11 2.64(17) . . . . ?
C8 C7 C12 O2 -177.93(10) . . . . ?
C10 C11 C12 C7 -0.80(17) . . . . ?
C10 C11 C12 O2 179.74(10) . . . . ?
C11 C10 C9 C8 1.25(18) . . . . ?
C12 C11 C10 C9 -1.20(18) . . . . ?
C12 C7 C8 C9 -2.57(17) . . . . ?
C12 O2 C6 C1 -12.74(15) . . . . ?
C12 O2 C6 C5 168.21(9) . . . . ?
C13 C1 C2 C3 -172.40(10) . . . . ?
C13 C1 C6 C5 172.84(10) . . . . ?
C13 C1 C6 O2 -6.14(16) . . . . ?
C13 C14 C15 C16 177.37(10) . . . . ?
C13 C14 C19 C18 -177.29(10) . . . . ?
C13 C7 C12 C11 -172.01(10) . . . . ?
C13 C7 C12 O2 7.42(16) . . . . ?
C13 C7 C8 C9 172.02(10) . . . . ?
C14 C13 C1 C2 -39.02(14) . . . . ?
C14 C13 C1 C6 147.46(10) . . . . ?
C14 C13 C7 C12 -148.56(10) . . . . ?
C14 C13 C7 C8 37.03(14) . . . . ?
C14 C19 C18 C17 -0.11(17) . . . . ?
C15 C14 C13 C1 120.59(11) . . . . ?
C15 C14 C13 C7 -115.99(11) . . . . ?
C15 C14 C13 O1 2.09(13) . . . . ?
C15 C14 C19 C18 1.28(17) . . . . ?
C15 C16 C17 C18 1.30(17) . . . . ?
C15 C16 C17 O3 -179.84(10) . . . . ?
C16 C17 C18 C19 -1.19(17) . . . . ?
C17 C16 C15 C14 -0.11(17) . . . . ?
C19 C14 C13 C1 -60.89(13) . . . . ?
C19 C14 C13 C7 62.53(13) . . . . ?
C19 C14 C13 O1 -179.39(9) . . . . ?
C19 C14 C15 C16 -1.17(16) . . . . ?
C20 O3 C17 C16 176.85(11) . . . . ?
C20 O3 C17 C18 -4.35(17) . . . . ?
C1G C2G C3G C1G 0.5(3) . . . 2 ?
C3G C2G C1G C3G -0.5(3) . . . 2 ?
