#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/03/7200313.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_7200313
loop_
_publ_author_name
'Linder, Peter W.'
'Nassimbeni, Luigi R.'
'Su, Hong'
_publ_section_title
;
 Selectivity of butanol isomers by enclathration
;
_journal_issue                   1
_journal_name_full               CrystEngComm
_journal_page_first              192
_journal_paper_doi               10.1039/b812887a
_journal_volume                  11
_journal_year                    2009
_chemical_formula_sum            'C22 H30 O3'
_chemical_formula_weight         342.46
_chemical_name_systematic
;
1,1-bis(4-hydroxyphenyl)cyclohexane iso-butanol 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                94.029(2)
_cell_angle_beta                 100.875(3)
_cell_angle_gamma                101.498(3)
_cell_formula_units_Z            2
_cell_length_a                   6.2259(2)
_cell_length_b                   10.8829(6)
_cell_length_c                   15.2046(8)
_cell_measurement_temperature    173(2)
_cell_volume                     985.15(8)
_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, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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    0.0489
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            3719
_diffrn_reflns_theta_full        25.67
_diffrn_reflns_theta_max         25.67
_diffrn_reflns_theta_min         2.23
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            P-1
_exptl_crystal_density_diffrn    1.154
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       needle
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       0.016(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3719
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0839
_refine_ls_R_factor_gt           0.0443
_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)+(0.0553P)²+0.1753P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1022
_refine_ls_wR_factor_ref         0.1202
_reflns_number_gt                2481
_reflns_number_total             3719
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b812887a.txt
_cod_data_source_block           HisoBuOH
_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               7200313
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 0.0606(2) 0.55709(12) 0.16352(8) 0.0340(3) Uani 1 1 d . . .
H1 H 0.171(4) 0.578(2) 0.1340(17) 0.078(8) Uiso 1 1 d . . .
O2 O -0.2008(2) -0.28308(12) 0.19115(8) 0.0377(3) Uani 1 1 d . . .
H2 H -0.095(4) -0.337(2) 0.1844(15) 0.067(7) Uiso 1 1 d . . .
C1 C 0.2070(2) 0.18855(15) 0.40658(11) 0.0243(4) Uani 1 1 d . . .
C2 C 0.4594(3) 0.20252(16) 0.44672(11) 0.0284(4) Uani 1 1 d . . .
H2A H 0.4802 0.1295 0.4802 0.034 Uiso 1 1 calc R . .
H2B H 0.5414 0.2015 0.3970 0.034 Uiso 1 1 calc R . .
C3 C 0.5585(3) 0.32428(17) 0.51011(12) 0.0320(4) Uani 1 1 d . . .
H3A H 0.7197 0.3291 0.5339 0.038 Uiso 1 1 calc R . .
H3B H 0.5449 0.3977 0.4762 0.038 Uiso 1 1 calc R . .
C4 C 0.4388(3) 0.32964(19) 0.58817(12) 0.0354(5) Uani 1 1 d . . .
H4A H 0.4997 0.4114 0.6262 0.042 Uiso 1 1 calc R . .
H4B H 0.4658 0.2615 0.6259 0.042 Uiso 1 1 calc R . .
C5 C 0.1880(3) 0.31471(17) 0.55379(11) 0.0304(4) Uani 1 1 d . . .
H5A H 0.1600 0.3893 0.5235 0.036 Uiso 1 1 calc R . .
H5B H 0.1118 0.3105 0.6054 0.036 Uiso 1 1 calc R . .
C6 C 0.0906(3) 0.19517(16) 0.48752(11) 0.0266(4) Uani 1 1 d . . .
H6A H -0.0707 0.1909 0.4645 0.032 Uiso 1 1 calc R . .
H6B H 0.1036 0.1206 0.5202 0.032 Uiso 1 1 calc R . .
C13 C 0.1068(3) 0.06022(16) 0.34915(10) 0.0241(4) Uani 1 1 d . . .
C18 C 0.2280(3) -0.03109(17) 0.33551(11) 0.0291(4) Uani 1 1 d . . .
H18 H 0.3826 -0.0151 0.3630 0.035 Uiso 1 1 calc R . .
C17 C 0.1299(3) -0.14510(16) 0.28290(11) 0.0310(4) Uani 1 1 d . . .
H17 H 0.2173 -0.2055 0.2744 0.037 Uiso 1 1 calc R . .
C16 C -0.0952(3) -0.17059(16) 0.24291(11) 0.0287(4) Uani 1 1 d . . .
C15 C -0.2208(3) -0.08214(16) 0.25541(11) 0.0299(4) Uani 1 1 d . . .
H15 H -0.3759 -0.0993 0.2285 0.036 Uiso 1 1 calc R . .
C14 C -0.1203(3) 0.03144(17) 0.30722(11) 0.0292(4) Uani 1 1 d . . .
H14 H -0.2082 0.0920 0.3146 0.035 Uiso 1 1 calc R . .
C7 C 0.1709(2) 0.29148(15) 0.34403(10) 0.0241(4) Uani 1 1 d . . .
C12 C 0.0030(3) 0.35885(16) 0.34451(11) 0.0273(4) Uani 1 1 d . . .
H12 H -0.0899 0.3444 0.3873 0.033 Uiso 1 1 calc R . .
C11 C -0.0327(3) 0.44635(16) 0.28444(11) 0.0284(4) Uani 1 1 d . . .
H11 H -0.1491 0.4905 0.2863 0.034 Uiso 1 1 calc R . .
C10 C 0.1005(3) 0.46943(15) 0.22191(11) 0.0259(4) Uani 1 1 d . . .
C9 C 0.2672(3) 0.40255(17) 0.21881(11) 0.0302(4) Uani 1 1 d . . .
H9 H 0.3588 0.4169 0.1756 0.036 Uiso 1 1 calc R . .
C8 C 0.2994(3) 0.31508(16) 0.27877(11) 0.0292(4) Uani 1 1 d . . .
H8 H 0.4132 0.2694 0.2755 0.035 Uiso 1 1 calc R . .
O1G O 0.3904(2) 0.62318(14) 0.08190(9) 0.0480(4) Uani 1 1 d . . .
H1G H 0.515(4) 0.660(2) 0.1170(16) 0.070(8) Uiso 1 1 d . . .
C1G C 0.3912(4) 0.6625(2) -0.00578(13) 0.0478(5) Uani 1 1 d . . .
H1G1 H 0.2635 0.6080 -0.0493 0.057 Uiso 1 1 calc R . .
H1G2 H 0.5307 0.6503 -0.0240 0.057 Uiso 1 1 calc R . .
C2G C 0.3754(4) 0.7980(2) -0.01101(14) 0.0508(6) Uani 1 1 d . . .
H2G H 0.5029 0.8519 0.0343 0.061 Uiso 1 1 calc R . .
C3G C 0.4002(5) 0.8339(2) -0.10423(16) 0.0831(9) Uani 1 1 d . . .
H3G1 H 0.5419 0.8180 -0.1164 0.125 Uiso 1 1 calc R . .
H3G2 H 0.3993 0.9235 -0.1065 0.125 Uiso 1 1 calc R . .
H3G3 H 0.2752 0.7831 -0.1497 0.125 Uiso 1 1 calc R . .
C4G C 0.1600(5) 0.8213(3) 0.0114(2) 0.0924(10) Uani 1 1 d . . .
H4G1 H 0.1556 0.9104 0.0080 0.139 Uiso 1 1 calc R . .
H4G2 H 0.1520 0.8003 0.0724 0.139 Uiso 1 1 calc R . .
H4G3 H 0.0324 0.7685 -0.0318 0.139 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
C13 C1 C7 106.88(12) . . ?
C13 C1 C6 108.74(13) . . ?
C7 C1 C6 113.00(13) . . ?
C13 C1 C2 111.35(13) . . ?
C7 C1 C2 110.54(13) . . ?
C6 C1 C2 106.38(13) . . ?
C3 C2 C1 112.43(13) . . ?
C4 C3 C2 111.03(14) . . ?
C3 C4 C5 110.76(14) . . ?
C4 C5 C6 111.23(14) . . ?
C5 C6 C1 113.74(13) . . ?
C18 C13 C14 116.59(15) . . ?
C18 C13 C1 124.20(14) . . ?
C14 C13 C1 119.21(14) . . ?
C17 C18 C13 121.94(15) . . ?
C16 C17 C18 119.89(16) . . ?
O2 C16 C15 118.30(14) . . ?
O2 C16 C17 122.02(16) . . ?
C15 C16 C17 119.67(16) . . ?
C16 C15 C14 119.77(15) . . ?
C15 C14 C13 122.14(16) . . ?
C12 C7 C8 116.46(15) . . ?
C12 C7 C1 123.24(14) . . ?
C8 C7 C1 120.16(14) . . ?
C11 C12 C7 121.98(15) . . ?
C10 C11 C12 120.14(15) . . ?
O1 C10 C11 118.56(15) . . ?
O1 C10 C9 122.12(15) . . ?
C11 C10 C9 119.31(15) . . ?
C8 C9 C10 119.77(16) . . ?
C9 C8 C7 122.32(15) . . ?
O1G C1G C2G 113.57(17) . . ?
C1G C2G C4G 111.5(2) . . ?
C1G C2G C3G 109.38(18) . . ?
C4G C2G C3G 111.6(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 C10 1.375(2) . ?
O2 C16 1.378(2) . ?
C1 C13 1.542(2) . ?
C1 C7 1.543(2) . ?
C1 C6 1.546(2) . ?
C1 C2 1.547(2) . ?
C2 C3 1.528(2) . ?
C3 C4 1.520(2) . ?
C4 C5 1.522(2) . ?
C5 C6 1.532(2) . ?
C13 C18 1.389(2) . ?
C13 C14 1.400(2) . ?
C18 C17 1.388(2) . ?
C17 C16 1.382(2) . ?
C16 C15 1.380(2) . ?
C15 C14 1.382(2) . ?
C7 C12 1.392(2) . ?
C7 C8 1.395(2) . ?
C12 C11 1.386(2) . ?
C11 C10 1.379(2) . ?
C10 C9 1.387(2) . ?
C9 C8 1.381(2) . ?
O1G C1G 1.429(2) . ?
C1G C2G 1.504(3) . ?
C2G C4G 1.508(3) . ?
C2G C3G 1.524(3) . ?
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 O1G 0.89(3) 1.71(3) 2.6021(19) 177(2) .
O2 H2 O1 0.98(2) 1.69(3) 2.6714(18) 173(2) 1_545
O1G H1G O2 0.86(2) 1.87(2) 2.7218(18) 172(2) 1_665
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653543
