#------------------------------------------------------------------------------
#$Date: 2016-02-16 03:10:39 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176453 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/38/7053815.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_7053815
loop_
_publ_author_name
'Jacobs, Ayesha'
'Nassimbeni, Luigi R.'
'Nohako, Kanyisa L.'
'Ramon, Gaelle'
'Taljaard, Jana H.'
_publ_section_title
;
 Enclathration by a xanthenol host via solid--solid reactions: structures
 and kinetics
;
_journal_issue                   9
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              1960
_journal_paper_doi               10.1039/b906720e
_journal_volume                  33
_journal_year                    2009
_chemical_formula_moiety         'C20 H16 O3.C4 H3 N O0.5'
_chemical_formula_sum            'C24 H18.5 N O3.5'
_chemical_formula_weight         376.90
_chemical_name_systematic
;
9-(4-methoxyphenyl)-9H-xanthen-9-ol 8-hydroxyquinoline 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                96.36(3)
_cell_angle_beta                 91.64(3)
_cell_angle_gamma                109.14(3)
_cell_formula_units_Z            2
_cell_length_a                   8.3982(17)
_cell_length_b                   8.9905(18)
_cell_length_c                   12.954(3)
_cell_measurement_reflns_used    'All data'
_cell_measurement_temperature    173(2)
_cell_volume                     916.1(4)
_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, 1999)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Nonius KappaCCD'
_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  0.036
_diffrn_reflns_av_sigmaI/netI    0.0366
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13605
_diffrn_reflns_theta_full        25.64
_diffrn_reflns_theta_max         25.64
_diffrn_reflns_theta_min         2.93
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             395
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.29
_refine_diff_density_max         0.971
_refine_diff_density_min         -0.465
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       N/A
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     268
_refine_ls_number_reflns         3435
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0796
_refine_ls_R_factor_gt           0.0551
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0723P)²+0.6952P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1349
_refine_ls_wR_factor_ref         0.1544
_reflns_number_gt                2556
_reflns_number_total             3435
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b906720esup1.cif
_cod_data_source_block           c:\ctech_~1\a18hydrq\a18hydrq
_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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        916.1(3)
_cod_original_sg_symbol_H-M      P-1
_cod_original_formula_sum        'C24 H18.50 N O3.50'
_cod_database_code               7053815
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
O1 O -0.08802(18) -0.01682(16) 0.61799(12) 0.0291(4) Uani 1 1 d .
C1 C 0.2072(3) 0.1227(2) 0.67478(16) 0.0228(5) Uani 1 1 d .
H1 H 0.200(2) 0.189(2) 0.4882(12) 0.054(8) Uiso 1 1 d D
O2 O 0.27472(17) 0.27981(17) 0.53193(11) 0.0250(4) Uani 1 1 d D
C2 C 0.3551(3) 0.1114(3) 0.71974(17) 0.0279(5) Uani 1 1 d .
H2 H 0.4540 0.2026 0.7297 0.034 Uiso 1 1 calc R
O3 O 0.6412(2) 0.81494(19) 0.89347(12) 0.0359(4) Uani 1 1 d .
C3 C 0.3611(3) -0.0297(3) 0.75012(18) 0.0322(5) Uani 1 1 d .
H3 H 0.4635 -0.0351 0.7797 0.039 Uiso 1 1 calc R
C4 C 0.2166(3) -0.1632(3) 0.73714(19) 0.0341(6) Uani 1 1 d .
H4 H 0.2201 -0.2600 0.7582 0.041 Uiso 1 1 calc R
C5 C 0.0688(3) -0.1554(3) 0.69396(19) 0.0311(5) Uani 1 1 d .
H5 H -0.0304 -0.2464 0.6854 0.037 Uiso 1 1 calc R
C6 C 0.0656(3) -0.0131(3) 0.66292(16) 0.0251(5) Uani 1 1 d .
C7 C 0.0224(3) 0.2700(2) 0.61885(16) 0.0226(5) Uani 1 1 d .
C8 C -0.0170(3) 0.4061(3) 0.60713(17) 0.0276(5) Uani 1 1 d .
H8 H 0.0702 0.5064 0.6179 0.033 Uiso 1 1 calc R
C9 C -0.1809(3) 0.3990(3) 0.58011(18) 0.0315(5) Uani 1 1 d .
H9 H -0.2045 0.4936 0.5723 0.038 Uiso 1 1 calc R
C10 C -0.3098(3) 0.2536(3) 0.56448(18) 0.0314(5) Uani 1 1 d .
H10 H -0.4213 0.2481 0.5440 0.038 Uiso 1 1 calc R
C11 C -0.2757(3) 0.1164(3) 0.57873(18) 0.0292(5) Uani 1 1 d .
H11 H -0.3638 0.0166 0.5701 0.035 Uiso 1 1 calc R
C12 C -0.1108(3) 0.1267(2) 0.60588(16) 0.0237(5) Uani 1 1 d .
C13 C 0.2042(2) 0.2742(2) 0.63295(16) 0.0217(4) Uani 1 1 d .
C14 C 0.3175(2) 0.4216(2) 0.70214(16) 0.0212(4) Uani 1 1 d .
C15 C 0.4512(3) 0.5347(2) 0.66425(17) 0.0251(5) Uani 1 1 d .
H15 H 0.4711 0.5231 0.5925 0.030 Uiso 1 1 calc R
C16 C 0.5564(3) 0.6647(3) 0.73015(18) 0.0273(5) Uani 1 1 d .
H16 H 0.6471 0.7413 0.7030 0.033 Uiso 1 1 calc R
C17 C 0.5295(3) 0.6832(2) 0.83529(17) 0.0257(5) Uani 1 1 d .
C18 C 0.3947(3) 0.5727(3) 0.87429(17) 0.0275(5) Uani 1 1 d .
H18 H 0.3742 0.5850 0.9459 0.033 Uiso 1 1 calc R
C19 C 0.2898(3) 0.4435(2) 0.80704(17) 0.0263(5) Uani 1 1 d .
H19 H 0.1971 0.3686 0.8337 0.032 Uiso 1 1 calc R
C20 C 0.6177(4) 0.8378(3) 1.00219(19) 0.0432(6) Uani 1 1 d .
H20B H 0.5071 0.8499 1.0117 0.065 Uiso 1 1 calc R
H20A H 0.7066 0.9334 1.0353 0.065 Uiso 1 1 calc R
H20C H 0.6233 0.7456 1.0341 0.065 Uiso 1 1 calc R
O1G O 1.0017(6) 0.1740(6) 1.0295(4) 0.0732(13) Uani 0.50 1 d P
H1G H 1.0712 0.2218 1.0800 0.088 Uiso 0.50 1 calc PR
C2G C 0.9532(4) 0.2775(5) 0.9835(3) 0.0689(10) Uani 1 1 d .
C3G C 1.1966(5) 0.6461(6) 1.1503(3) 0.0866(14) Uani 1 1 d .
H3G H 1.2739 0.6798 1.2100 0.104 Uiso 1 1 calc R
N4G N 1.1299(4) 0.4829(5) 1.1131(3) 0.0957(12) Uani 1 1 d .
C5G C 1.0249(3) 0.4482(4) 1.0260(2) 0.0536(8) Uani 1 1 d .
C6G C 0.8488(4) 0.2370(5) 0.8993(3) 0.0797(13) Uani 1 1 d .
H6G H 0.8028 0.1284 0.8709 0.096 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'
N N 0.0061 0.0033 '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
C6 O1 C12 118.23(16) . .
C6 C1 C2 117.15(19) . .
C6 C1 C13 121.16(18) . .
C2 C1 C13 121.55(19) . .
C13 O2 H1 105.3(10) . .
C3 C2 C1 121.5(2) . .
C3 C2 H2 119.2 . .
C1 C2 H2 119.2 . .
C17 O3 C20 117.22(19) . .
C2 C3 C4 119.7(2) . .
C2 C3 H3 120.1 . .
C4 C3 H3 120.1 . .
C5 C4 C3 120.1(2) . .
C5 C4 H4 119.9 . .
C3 C4 H4 119.9 . .
C4 C5 C6 119.4(2) . .
C4 C5 H5 120.3 . .
C6 C5 H5 120.3 . .
C1 C6 O1 122.33(18) . .
C1 C6 C5 122.12(19) . .
O1 C6 C5 115.54(19) . .
C8 C7 C12 116.96(19) . .
C8 C7 C13 121.71(18) . .
C12 C7 C13 120.98(18) . .
C9 C8 C7 121.6(2) . .
C9 C8 H8 119.2 . .
C7 C8 H8 119.2 . .
C10 C9 C8 119.9(2) . .
C10 C9 H9 120.0 . .
C8 C9 H9 120.0 . .
C11 C10 C9 119.9(2) . .
C11 C10 H10 120.1 . .
C9 C10 H10 120.1 . .
C10 C11 C12 119.1(2) . .
C10 C11 H11 120.5 . .
C12 C11 H11 120.5 . .
C11 C12 O1 115.19(18) . .
C11 C12 C7 122.49(19) . .
O1 C12 C7 122.31(18) . .
O2 C13 C7 108.32(16) . .
O2 C13 C14 105.95(16) . .
C7 C13 C14 113.26(16) . .
O2 C13 C1 108.61(15) . .
C7 C13 C1 109.35(16) . .
C14 C13 C1 111.16(16) . .
C19 C14 C15 118.21(19) . .
C19 C14 C13 119.65(18) . .
C15 C14 C13 122.12(18) . .
C14 C15 C16 120.8(2) . .
C14 C15 H15 119.6 . .
C16 C15 H15 119.6 . .
C17 C16 C15 120.3(2) . .
C17 C16 H16 119.8 . .
C15 C16 H16 119.8 . .
O3 C17 C16 115.62(19) . .
O3 C17 C18 124.7(2) . .
C16 C17 C18 119.7(2) . .
C17 C18 C19 119.2(2) . .
C17 C18 H18 120.4 . .
C19 C18 H18 120.4 . .
C14 C19 C18 121.7(2) . .
C14 C19 H19 119.2 . .
C18 C19 H19 119.2 . .
O3 C20 H20B 109.5 . .
O3 C20 H20A 109.5 . .
H20B C20 H20A 109.5 . .
O3 C20 H20C 109.5 . .
H20B C20 H20C 109.5 . .
H20A C20 H20C 109.5 . .
C2G O1G H1G 109.5 . .
C6G C2G O1G 122.9(4) . .
C6G C2G C5G 118.5(4) . .
O1G C2G C5G 118.5(4) . .
N4G C3G C6G 122.1(4) . 2_767
N4G C3G H3G 119.0 . .
C6G C3G H3G 119.0 2_767 .
C5G N4G C3G 114.2(4) . .
N4G C5G C5G 127.5(4) . 2_767
N4G C5G C2G 116.0(4) . .
C5G C5G C2G 116.5(4) 2_767 .
C2G C6G C3G 121.2(4) . 2_767
C2G C6G H6G 119.4 . .
C3G C6G H6G 119.4 2_767 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C6 1.389(2) .
O1 C12 1.390(2) .
C1 C6 1.388(3) .
C1 C2 1.395(3) .
C1 C13 1.528(3) .
O2 C13 1.451(2) .
O2 H1 0.960(2) .
C2 C3 1.384(3) .
C2 H2 0.9500 .
O3 C17 1.373(3) .
O3 C20 1.429(3) .
C3 C4 1.389(3) .
C3 H3 0.9500 .
C4 C5 1.373(3) .
C4 H4 0.9500 .
C5 C6 1.391(3) .
C5 H5 0.9500 .
C7 C8 1.390(3) .
C7 C12 1.391(3) .
C7 C13 1.521(3) .
C8 C9 1.389(3) .
C8 H8 0.9500 .
C9 C10 1.387(3) .
C9 H9 0.9500 .
C10 C11 1.384(3) .
C10 H10 0.9500 .
C11 C12 1.389(3) .
C11 H11 0.9500 .
C13 C14 1.525(3) .
C14 C19 1.389(3) .
C14 C15 1.389(3) .
C15 C16 1.391(3) .
C15 H15 0.9500 .
C16 C17 1.388(3) .
C16 H16 0.9500 .
C17 C18 1.389(3) .
C18 C19 1.394(3) .
C18 H18 0.9500 .
C19 H19 0.9500 .
C20 H20B 0.9800 .
C20 H20A 0.9800 .
C20 H20C 0.9800 .
O1G C2G 1.321(6) .
O1G H1G 0.8400 .
C2G C6G 1.319(5) .
C2G C5G 1.486(5) .
C3G N4G 1.411(6) .
C3G C6G 1.435(6) 2_767
C3G H3G 0.9500 .
N4G C5G 1.353(4) .
C5G C5G 1.370(6) 2_767
C6G C3G 1.435(6) 2_767
C6G H6G 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_4
C6 C1 C2 C3 0.8(3) . .
C13 C1 C2 C3 -174.8(2) . .
C1 C2 C3 C4 -0.9(3) . .
C2 C3 C4 C5 0.3(4) . .
C3 C4 C5 C6 0.4(4) . .
C2 C1 C6 O1 -179.14(18) . .
C13 C1 C6 O1 -3.5(3) . .
C2 C1 C6 C5 -0.1(3) . .
C13 C1 C6 C5 175.50(19) . .
C12 O1 C6 C1 -14.5(3) . .
C12 O1 C6 C5 166.41(19) . .
C4 C5 C6 C1 -0.5(3) . .
C4 C5 C6 O1 178.7(2) . .
C12 C7 C8 C9 -2.2(3) . .
C13 C7 C8 C9 171.0(2) . .
C7 C8 C9 C10 0.2(3) . .
C8 C9 C10 C11 1.8(3) . .
C9 C10 C11 C12 -1.7(3) . .
C10 C11 C12 O1 -179.64(19) . .
C10 C11 C12 C7 -0.4(3) . .
C6 O1 C12 C11 -168.60(19) . .
C6 O1 C12 C7 12.1(3) . .
C8 C7 C12 C11 2.3(3) . .
C13 C7 C12 C11 -170.99(19) . .
C8 C7 C12 O1 -178.48(19) . .
C13 C7 C12 O1 8.2(3) . .
C8 C7 C13 O2 -78.2(2) . .
C12 C7 C13 O2 94.8(2) . .
C8 C7 C13 C14 39.1(3) . .
C12 C7 C13 C14 -147.98(19) . .
C8 C7 C13 C1 163.64(19) . .
C12 C7 C13 C1 -23.4(3) . .
C6 C1 C13 O2 -96.8(2) . .
C2 C1 C13 O2 78.6(2) . .
C6 C1 C13 C7 21.2(3) . .
C2 C1 C13 C7 -163.41(19) . .
C6 C1 C13 C14 146.97(19) . .
C2 C1 C13 C14 -37.6(3) . .
O2 C13 C14 C19 -175.01(17) . .
C7 C13 C14 C19 66.4(2) . .
C1 C13 C14 C19 -57.2(2) . .
O2 C13 C14 C15 3.6(2) . .
C7 C13 C14 C15 -115.0(2) . .
C1 C13 C14 C15 121.4(2) . .
C19 C14 C15 C16 1.2(3) . .
C13 C14 C15 C16 -177.44(18) . .
C14 C15 C16 C17 0.2(3) . .
C20 O3 C17 C16 -179.9(2) . .
C20 O3 C17 C18 1.1(3) . .
C15 C16 C17 O3 179.57(18) . .
C15 C16 C17 C18 -1.3(3) . .
O3 C17 C18 C19 179.95(19) . .
C16 C17 C18 C19 0.9(3) . .
C15 C14 C19 C18 -1.6(3) . .
C13 C14 C19 C18 177.07(18) . .
C17 C18 C19 C14 0.6(3) . .
C6G C3G N4G C5G 1.8(5) 2_767 .
C3G N4G C5G C5G -1.9(5) . 2_767
C3G N4G C5G C2G 179.4(3) . .
C6G C2G C5G N4G 179.4(3) . .
O1G C2G C5G N4G -3.1(5) . .
C6G C2G C5G C5G 0.5(5) . 2_767
O1G C2G C5G C5G 178.0(4) . 2_767
O1G C2G C6G C3G -177.9(4) . 2_767
C5G C2G C6G C3G -0.6(5) . 2_767
