#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/88/4508875.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_4508875
loop_
_publ_author_name
'Curtis, Elizabeth'
'Nassimbeni, Luigi R.'
'Su, Hong'
'Taljaard, Jana H.'
_publ_section_title
;
 Xanthenol Clathrates:  Structures and Solid−Solid Reactions
;
_journal_issue                   12
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              2716
_journal_paper_doi               10.1021/cg060384q
_journal_volume                  6
_journal_year                    2006
_chemical_formula_moiety         'C20 H16 O3, C5 H4 O0.5'
_chemical_formula_sum            'C25 H20 O3.5'
_chemical_formula_weight         376.41
_chemical_melting_point          ?
_chemical_name_systematic
; 
 9-(4-methoxyphenyl)-9H-xanthen-9-ol beta-naphthol 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                96.162(1)
_cell_angle_beta                 93.767(1)
_cell_angle_gamma                109.314(1)
_cell_formula_units_Z            2
_cell_length_a                   8.3914(2)
_cell_length_b                   9.1177(2)
_cell_length_c                   12.8162(3)
_cell_measurement_temperature    113(2)
_cell_volume                     914.67(4)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT program (Nonius, 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, 1997)'
_diffrn_ambient_temperature      113(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_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  0.0196
_diffrn_reflns_av_sigmaI/netI    0.0436
_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            6951
_diffrn_reflns_theta_full        26.78
_diffrn_reflns_theta_max         26.78
_diffrn_reflns_theta_min         2.86
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.9839
_exptl_absorpt_correction_T_min  0.9708
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_refine_diff_density_max         1.041
_refine_diff_density_min         -0.417
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       0.011(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3837
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0796
_refine_ls_R_factor_gt           0.0570
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0855P)²+0.5788P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1541
_refine_ls_wR_factor_ref         0.1692
_reflns_number_gt                2831
_reflns_number_total             3837
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg060384qsup6.cif
_cod_data_source_block           HNOL
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value 'not measured' was changed to '?' -
the value is undefined or not given.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      P-1
_cod_original_formula_sum        'C25 H20 O3.50'
_cod_database_code               4508875
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
O2 O 0.41792(17) -0.01306(16) 0.11497(11) 0.0243(4) Uani 1 1 d .
O1 O 0.77921(17) 0.28268(16) 0.03048(10) 0.0220(3) Uani 1 1 d D
O3 O 1.13740(19) 0.82040(17) 0.40282(11) 0.0291(4) Uani 1 1 d .
C7 C 0.7127(2) 0.2752(2) 0.13225(15) 0.0198(4) Uani 1 1 d .
C14 C 0.8265(2) 0.4212(2) 0.20410(15) 0.0199(4) Uani 1 1 d .
C17 C 1.0315(3) 0.6853(2) 0.34174(16) 0.0228(4) Uani 1 1 d .
C6 C 0.5292(2) 0.2698(2) 0.11715(15) 0.0203(4) Uani 1 1 d .
C8 C 0.7180(2) 0.1256(2) 0.17304(15) 0.0198(4) Uani 1 1 d .
C18 C 1.0638(3) 0.6652(2) 0.23739(16) 0.0236(5) Uani 1 1 d .
H18 H 1.1560 0.7411 0.2127 0.028 Uiso 1 1 calc R
C1 C 0.3951(3) 0.1286(2) 0.10337(15) 0.0209(4) Uani 1 1 d .
C13 C 0.5750(2) -0.0092(2) 0.15945(15) 0.0216(4) Uani 1 1 d .
C2 C 0.2280(3) 0.1182(2) 0.07651(16) 0.0250(5) Uani 1 1 d .
H2 H 0.1391 0.0195 0.0668 0.030 Uiso 1 1 calc R
C9 C 0.8692(3) 0.1141(2) 0.21793(16) 0.0238(4) Uani 1 1 d .
H9 H 0.9689 0.2045 0.2294 0.029 Uiso 1 1 calc R
C16 C 0.8968(3) 0.5747(2) 0.37841(16) 0.0235(4) Uani 1 1 d .
H16 H 0.8740 0.5881 0.4498 0.028 Uiso 1 1 calc R
C19 C 0.9616(2) 0.5341(2) 0.16891(16) 0.0214(4) Uani 1 1 d .
H19 H 0.9840 0.5213 0.0974 0.026 Uiso 1 1 calc R
C12 C 0.5796(3) -0.1503(2) 0.18880(17) 0.0260(5) Uani 1 1 d .
H12 H 0.4794 -0.2402 0.1795 0.031 Uiso 1 1 calc R
C5 C 0.4891(3) 0.4052(2) 0.10696(16) 0.0235(4) Uani 1 1 d .
H5 H 0.5774 0.5044 0.1183 0.028 Uiso 1 1 calc R
C4 C 0.3239(3) 0.3978(3) 0.08069(17) 0.0270(5) Uani 1 1 d .
H4 H 0.2995 0.4911 0.0739 0.032 Uiso 1 1 calc R
C15 C 0.7959(3) 0.4440(2) 0.30880(16) 0.0231(4) Uani 1 1 d .
H15 H 0.7036 0.3683 0.3336 0.028 Uiso 1 1 calc R
C10 C 0.8766(3) -0.0263(2) 0.24599(17) 0.0265(5) Uani 1 1 d .
H10 H 0.9811 -0.0321 0.2750 0.032 Uiso 1 1 calc R
C20 C 1.1084(3) 0.8443(3) 0.51108(17) 0.0356(6) Uani 1 1 d .
H20A H 0.9947 0.8511 0.5150 0.053 Uiso 1 1 calc R
H20B H 1.1937 0.9419 0.5465 0.053 Uiso 1 1 calc R
H20C H 1.1168 0.7561 0.5459 0.053 Uiso 1 1 calc R
C3 C 0.1934(3) 0.2529(3) 0.06417(17) 0.0269(5) Uani 1 1 d .
H3 H 0.0802 0.2473 0.0443 0.032 Uiso 1 1 calc R
C11 C 0.7312(3) -0.1585(2) 0.23166(17) 0.0278(5) Uani 1 1 d .
H11 H 0.7360 -0.2546 0.2513 0.033 Uiso 1 1 calc R
C4G C 0.4537(3) 0.5222(4) 0.4610(2) 0.0443(7) Uani 1 1 d .
C5G C 0.3508(4) 0.4068(6) 0.3797(2) 0.0705(11) Uani 1 1 d .
H5G H 0.2861 0.4365 0.3276 0.085 Uiso 1 1 calc R
C3G C 0.4638(4) 0.6823(5) 0.4688(3) 0.0730(11) Uani 1 1 d .
H3G H 0.4022 0.7166 0.4175 0.088 Uiso 1 1 calc R
C1G C 0.6586(5) 0.7414(7) 0.6264(4) 0.0942(17) Uani 1 1 d .
H1G H 0.7300 0.8163 0.6820 0.113 Uiso 1 1 calc R
O1G O 0.5600(9) 0.9300(9) 0.5673(6) 0.119(2) Uiso 0.50 1 d P
C2G C 0.5665(6) 0.7873(5) 0.5535(5) 0.0960(17) Uani 1 1 d .
H1 H 0.706(3) 0.193(2) -0.0160(17) 0.047(8) 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
C13 O2 C1 118.19(15) .
C7 O1 H1 106.7(17) .
C17 O3 C20 117.27(17) .
O1 C7 C14 106.24(15) .
O1 C7 C6 108.37(15) .
C14 C7 C6 112.41(15) .
O1 C7 C8 108.71(15) .
C14 C7 C8 111.66(15) .
C6 C7 C8 109.30(15) .
C15 C14 C19 118.30(18) .
C15 C14 C7 119.31(17) .
C19 C14 C7 122.40(17) .
O3 C17 C18 115.84(18) .
O3 C17 C16 123.91(18) .
C18 C17 C16 120.23(18) .
C1 C6 C5 116.95(18) .
C1 C6 C7 121.33(17) .
C5 C6 C7 121.47(17) .
C13 C8 C9 117.08(18) .
C13 C8 C7 121.09(17) .
C9 C8 C7 121.63(17) .
C17 C18 C19 120.12(18) .
C17 C18 H18 119.9 .
C19 C18 H18 119.9 .
C6 C1 O2 122.36(17) .
C6 C1 C2 122.57(18) .
O2 C1 C2 115.07(17) .
O2 C13 C12 115.26(17) .
O2 C13 C8 122.51(17) .
C12 C13 C8 122.22(18) .
C3 C2 C1 119.04(19) .
C3 C2 H2 120.5 .
C1 C2 H2 120.5 .
C10 C9 C8 121.42(19) .
C10 C9 H9 119.3 .
C8 C9 H9 119.3 .
C17 C16 C15 118.89(19) .
C17 C16 H16 120.6 .
C15 C16 H16 120.6 .
C18 C19 C14 120.65(18) .
C18 C19 H19 119.7 .
C14 C19 H19 119.7 .
C11 C12 C13 119.33(19) .
C11 C12 H12 120.3 .
C13 C12 H12 120.3 .
C4 C5 C6 121.46(19) .
C4 C5 H5 119.3 .
C6 C5 H5 119.3 .
C5 C4 C3 119.74(19) .
C5 C4 H4 120.1 .
C3 C4 H4 120.1 .
C14 C15 C16 121.81(19) .
C14 C15 H15 119.1 .
C16 C15 H15 119.1 .
C9 C10 C11 119.95(19) .
C9 C10 H10 120.0 .
C11 C10 H10 120.0 .
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 .
C2 C3 C4 120.17(19) .
C2 C3 H3 119.9 .
C4 C3 H3 119.9 .
C12 C11 C10 119.99(19) .
C12 C11 H11 120.0 .
C10 C11 H11 120.0 .
C4G C4G C5G 118.9(4) 2_666
C4G C4G C3G 118.5(4) 2_666
C5G C4G C3G 122.6(3) .
C1G C5G C4G 122.1(4) 2_666
C1G C5G H5G 118.9 2_666
C4G C5G H5G 118.9 .
C2G C3G C4G 118.3(4) .
C2G C3G H3G 120.8 .
C4G C3G H3G 120.8 .
C5G C1G C2G 120.3(4) 2_666
C5G C1G H1G 119.8 2_666
C2G C1G H1G 119.8 .
O1G C2G C1G 119.9(6) .
O1G C2G C3G 118.0(7) .
C1G C2G C3G 121.8(4) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O2 C13 1.389(2) .
O2 C1 1.389(2) .
O1 C7 1.451(2) .
O1 H1 0.9599(10) .
O3 C17 1.377(2) .
O3 C20 1.431(3) .
C7 C14 1.520(3) .
C7 C6 1.523(3) .
C7 C8 1.525(3) .
C14 C15 1.389(3) .
C14 C19 1.394(3) .
C17 C18 1.387(3) .
C17 C16 1.390(3) .
C6 C1 1.386(3) .
C6 C5 1.400(3) .
C8 C13 1.390(3) .
C8 C9 1.399(3) .
C18 C19 1.390(3) .
C18 H18 0.9500 .
C1 C2 1.391(3) .
C13 C12 1.390(3) .
C2 C3 1.375(3) .
C2 H2 0.9500 .
C9 C10 1.386(3) .
C9 H9 0.9500 .
C16 C15 1.392(3) .
C16 H16 0.9500 .
C19 H19 0.9500 .
C12 C11 1.381(3) .
C12 H12 0.9500 .
C5 C4 1.383(3) .
C5 H5 0.9500 .
C4 C3 1.393(3) .
C4 H4 0.9500 .
C15 H15 0.9500 .
C10 C11 1.387(3) .
C10 H10 0.9500 .
C20 H20A 0.9800 .
C20 H20B 0.9800 .
C20 H20C 0.9800 .
C3 H3 0.9500 .
C11 H11 0.9500 .
C4G C4G 1.400(5) 2_666
C4G C5G 1.409(4) .
C4G C3G 1.426(5) .
C5G C1G 1.321(6) 2_666
C5G H5G 0.9500 .
C3G C2G 1.395(7) .
C3G H3G 0.9500 .
C1G C5G 1.321(6) 2_666
C1G C2G 1.359(7) .
C1G H1G 0.9500 .
O1G C2G 1.314(8) .
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 0.9599(10) 1.903(4) 2.8593(19) 174(3) 2_655
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
O1 C7 C14 C15 -178.32(16) . .
C6 C7 C14 C15 63.3(2) . .
C8 C7 C14 C15 -59.9(2) . .
O1 C7 C14 C19 1.7(2) . .
C6 C7 C14 C19 -116.7(2) . .
C8 C7 C14 C19 120.03(19) . .
C20 O3 C17 C18 -179.55(18) . .
C20 O3 C17 C16 1.9(3) . .
O1 C7 C6 C1 95.7(2) . .
C14 C7 C6 C1 -147.20(18) . .
C8 C7 C6 C1 -22.6(2) . .
O1 C7 C6 C5 -78.4(2) . .
C14 C7 C6 C5 38.7(2) . .
C8 C7 C6 C5 163.29(17) . .
O1 C7 C8 C13 -97.2(2) . .
C14 C7 C8 C13 145.91(18) . .
C6 C7 C8 C13 20.9(2) . .
O1 C7 C8 C9 77.6(2) . .
C14 C7 C8 C9 -39.3(2) . .
C6 C7 C8 C9 -164.27(17) . .
O3 C17 C18 C19 -178.64(17) . .
C16 C17 C18 C19 0.0(3) . .
C5 C6 C1 O2 -177.79(17) . .
C7 C6 C1 O2 7.9(3) . .
C5 C6 C1 C2 2.5(3) . .
C7 C6 C1 C2 -171.86(18) . .
C13 O2 C1 C6 11.4(3) . .
C13 O2 C1 C2 -168.87(17) . .
C1 O2 C13 C12 167.33(17) . .
C1 O2 C13 C8 -13.1(3) . .
C9 C8 C13 O2 -179.45(17) . .
C7 C8 C13 O2 -4.4(3) . .
C9 C8 C13 C12 0.1(3) . .
C7 C8 C13 C12 175.11(18) . .
C6 C1 C2 C3 -0.7(3) . .
O2 C1 C2 C3 179.52(18) . .
C13 C8 C9 C10 1.1(3) . .
C7 C8 C9 C10 -173.97(18) . .
O3 C17 C16 C15 178.63(18) . .
C18 C17 C16 C15 0.2(3) . .
C17 C18 C19 C14 -0.4(3) . .
C15 C14 C19 C18 0.7(3) . .
C7 C14 C19 C18 -179.31(17) . .
O2 C13 C12 C11 178.64(18) . .
C8 C13 C12 C11 -0.9(3) . .
C1 C6 C5 C4 -2.2(3) . .
C7 C6 C5 C4 172.13(18) . .
C6 C5 C4 C3 0.2(3) . .
C19 C14 C15 C16 -0.6(3) . .
C7 C14 C15 C16 179.41(17) . .
C17 C16 C15 C14 0.2(3) . .
C8 C9 C10 C11 -1.3(3) . .
C1 C2 C3 C4 -1.4(3) . .
C5 C4 C3 C2 1.6(3) . .
C13 C12 C11 C10 0.6(3) . .
C9 C10 C11 C12 0.4(3) . .
C4G C4G C5G C1G -1.3(5) 2_666 2_666
C3G C4G C5G C1G -179.6(3) . 2_666
C4G C4G C3G C2G 0.3(5) 2_666 .
C5G C4G C3G C2G 178.6(3) . .
C5G C1G C2G O1G 171.6(5) 2_666 .
C5G C1G C2G C3G -1.9(6) 2_666 .
C4G C3G C2G O1G -172.1(5) . .
C4G C3G C2G C1G 1.5(5) . .
