#------------------------------------------------------------------------------
#$Date: 2016-03-26 16:21:06 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180334 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/03/7200312.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_7200312
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 2-butanol clathrate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 102.579(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.2995(10)
_cell_length_b                   28.658(2)
_cell_length_c                   10.9868(10)
_cell_measurement_temperature    173(2)
_cell_volume                     1935.8(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, 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 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0663
_diffrn_reflns_av_sigmaI/netI    0.0780
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10655
_diffrn_reflns_theta_full        25.36
_diffrn_reflns_theta_max         25.36
_diffrn_reflns_theta_min         2.84
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.175
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       needle
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.467
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       0.008(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   1.000
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3532
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.1080
_refine_ls_R_factor_gt           0.0564
_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)+(0.1002P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1433
_refine_ls_wR_factor_ref         0.1720
_reflns_number_gt                2105
_reflns_number_total             3532
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b812887a.txt
_cod_data_source_block           H2BuOH
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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      P21/n
_cod_database_code               7200312
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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 0.2761(3) 0.67153(6) 0.38938(14) 0.0397(5) Uani 1 1 d . . .
H1 H 0.154(7) 0.6897(14) 0.366(4) 0.121(15) Uiso 1 1 d . . .
O2 O 0.5463(3) 0.65869(6) 1.23517(15) 0.0420(5) Uani 1 1 d . . .
H2 H 0.449(4) 0.6630(9) 1.283(2) 0.055(8) Uiso 1 1 d . . .
C1 C 0.2423(3) 0.54862(8) 0.79716(19) 0.0291(6) Uani 1 1 d . . .
C2 C 0.3963(3) 0.50612(8) 0.8048(2) 0.0322(6) Uani 1 1 d . . .
H2A H 0.5456 0.5175 0.8073 0.039 Uiso 1 1 calc R . .
H2B H 0.3987 0.4892 0.8836 0.039 Uiso 1 1 calc R . .
C3 C 0.3316(3) 0.47204(8) 0.6958(2) 0.0368(6) Uani 1 1 d . . .
H3A H 0.4320 0.4450 0.7089 0.044 Uiso 1 1 calc R . .
H3B H 0.3447 0.4877 0.6175 0.044 Uiso 1 1 calc R . .
C4 C 0.0979(4) 0.45481(9) 0.6839(2) 0.0407(6) Uani 1 1 d . . .
H4A H 0.0551 0.4353 0.6080 0.049 Uiso 1 1 calc R . .
H4B H 0.0893 0.4353 0.7569 0.049 Uiso 1 1 calc R . .
C5 C -0.0577(4) 0.49585(8) 0.6761(2) 0.0380(6) Uani 1 1 d . . .
H5A H -0.2062 0.4841 0.6741 0.046 Uiso 1 1 calc R . .
H5B H -0.0613 0.5133 0.5979 0.046 Uiso 1 1 calc R . .
C6 C 0.0115(3) 0.52851(8) 0.7870(2) 0.0331(6) Uani 1 1 d . . .
H6A H 0.0070 0.5113 0.8646 0.040 Uiso 1 1 calc R . .
H6B H -0.0937 0.5546 0.7792 0.040 Uiso 1 1 calc R . .
C7 C 0.2493(3) 0.58054(8) 0.68489(19) 0.0278(5) Uani 1 1 d . . .
C8 C 0.0883(3) 0.61397(8) 0.6450(2) 0.0328(6) Uani 1 1 d . . .
H8 H -0.0288 0.6161 0.6865 0.039 Uiso 1 1 calc R . .
C9 C 0.0922(4) 0.64410(8) 0.5477(2) 0.0333(6) Uani 1 1 d . . .
H9 H -0.0217 0.6661 0.5222 0.040 Uiso 1 1 calc R . .
C10 C 0.2640(3) 0.64211(8) 0.48715(19) 0.0305(6) Uani 1 1 d . . .
C11 C 0.4270(3) 0.61006(8) 0.5252(2) 0.0320(6) Uani 1 1 d . . .
H11 H 0.5455 0.6086 0.4846 0.038 Uiso 1 1 calc R . .
C12 C 0.4191(3) 0.57990(8) 0.62248(19) 0.0313(6) Uani 1 1 d . . .
H12 H 0.5336 0.5580 0.6475 0.038 Uiso 1 1 calc R . .
C13 C 0.3155(3) 0.57818(8) 0.91620(19) 0.0286(5) Uani 1 1 d . . .
C14 C 0.5213(3) 0.59854(8) 0.9416(2) 0.0338(6) Uani 1 1 d . . .
H14 H 0.6129 0.5939 0.8844 0.041 Uiso 1 1 calc R . .
C15 C 0.5971(4) 0.62525(8) 1.0471(2) 0.0360(6) Uani 1 1 d . . .
H15 H 0.7386 0.6385 1.0620 0.043 Uiso 1 1 calc R . .
C16 C 0.4648(3) 0.63247(8) 1.13092(19) 0.0315(6) Uani 1 1 d . . .
C17 C 0.2608(4) 0.61316(9) 1.1085(2) 0.0361(6) Uani 1 1 d . . .
H17 H 0.1693 0.6182 1.1655 0.043 Uiso 1 1 calc R . .
C18 C 0.1878(3) 0.58617(8) 1.0025(2) 0.0342(6) Uani 1 1 d . . .
H18 H 0.0466 0.5728 0.9887 0.041 Uiso 1 1 calc R . .
O1G O -0.0864(3) 0.71153(7) 0.2837(2) 0.0644(6) Uani 1 1 d . . .
H1G H -0.208(5) 0.6930(11) 0.269(3) 0.085(11) Uiso 1 1 d . . .
C1G C -0.2465(6) 0.77808(13) 0.3723(3) 0.0837(11) Uani 1 1 d . . .
H1G1 H -0.3799 0.7600 0.3688 0.125 Uiso 1 1 calc R . .
H1G2 H -0.2829 0.8112 0.3600 0.125 Uiso 1 1 calc R . .
H1G3 H -0.1483 0.7737 0.4539 0.125 Uiso 1 1 calc R . .
C2G C -0.1353(5) 0.76142(11) 0.2701(3) 0.0657(9) Uani 1 1 d . . .
H2G H -0.2392 0.7661 0.1882 0.079 Uiso 1 1 calc R . .
C3G C 0.0622(5) 0.78662(11) 0.2664(3) 0.0750(10) Uani 1 1 d . . .
H3G1 H 0.1674 0.7820 0.3467 0.090 Uiso 1 1 calc R . .
H3G2 H 0.0283 0.8204 0.2579 0.090 Uiso 1 1 calc R . .
C4G C 0.1686(6) 0.77193(14) 0.1611(3) 0.0889(12) Uani 1 1 d . . .
H4G1 H 0.3020 0.7900 0.1653 0.133 Uiso 1 1 calc R . .
H4G2 H 0.0682 0.7776 0.0809 0.133 Uiso 1 1 calc R . .
H4G3 H 0.2043 0.7386 0.1690 0.133 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 107.27(18) . . ?
C13 C1 C6 111.66(16) . . ?
C7 C1 C6 110.69(16) . . ?
C13 C1 C2 108.55(17) . . ?
C7 C1 C2 112.48(16) . . ?
C6 C1 C2 106.22(18) . . ?
C3 C2 C1 113.75(17) . . ?
C2 C3 C4 111.13(18) . . ?
C5 C4 C3 110.56(19) . . ?
C4 C5 C6 111.22(18) . . ?
C5 C6 C1 112.83(17) . . ?
C12 C7 C8 116.03(19) . . ?
C12 C7 C1 123.04(18) . . ?
C8 C7 C1 120.83(18) . . ?
C9 C8 C7 122.6(2) . . ?
C8 C9 C10 119.5(2) . . ?
C11 C10 O1 118.8(2) . . ?
C11 C10 C9 119.4(2) . . ?
O1 C10 C9 121.9(2) . . ?
C10 C11 C12 120.2(2) . . ?
C11 C12 C7 122.2(2) . . ?
C18 C13 C14 116.5(2) . . ?
C18 C13 C1 123.96(19) . . ?
C14 C13 C1 119.53(18) . . ?
C15 C14 C13 122.3(2) . . ?
C14 C15 C16 119.4(2) . . ?
C17 C16 O2 122.45(19) . . ?
C17 C16 C15 119.8(2) . . ?
O2 C16 C15 117.79(19) . . ?
C16 C17 C18 120.1(2) . . ?
C13 C18 C17 121.9(2) . . ?
C3G C2G O1G 109.1(2) . . ?
C3G C2G C1G 113.6(3) . . ?
O1G C2G C1G 110.6(3) . . ?
C2G C3G C4G 114.1(3) . . ?
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 1.381(3) . ?
O2 C16 1.373(3) . ?
C1 C13 1.542(3) . ?
C1 C7 1.544(3) . ?
C1 C6 1.545(3) . ?
C1 C2 1.548(3) . ?
C2 C3 1.530(3) . ?
C3 C4 1.531(3) . ?
C4 C5 1.521(3) . ?
C5 C6 1.523(3) . ?
C7 C12 1.391(3) . ?
C7 C8 1.395(3) . ?
C8 C9 1.378(3) . ?
C9 C10 1.390(3) . ?
C10 C11 1.373(3) . ?
C11 C12 1.384(3) . ?
C13 C18 1.390(3) . ?
C13 C14 1.393(3) . ?
C14 C15 1.385(3) . ?
C15 C16 1.385(3) . ?
C16 C17 1.371(3) . ?
C17 C18 1.390(3) . ?
O1G C2G 1.463(4) . ?
C1G C2G 1.524(4) . ?
C2G C3G 1.447(4) . ?
C3G C4G 1.518(4) . ?
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 0.92(4) 1.71(4) 2.593(2) 162(4) .
O2 H2 O1 0.90(3) 1.77(3) 2.676(2) 175(2) 1_556
O1G H1G O2 0.92(3) 1.80(3) 2.719(3) 177(3) 1_454
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
C13 C1 C2 C3 176.05(17) . . . . ?
C7 C1 C2 C3 -65.4(2) . . . . ?
C6 C1 C2 C3 55.8(2) . . . . ?
C1 C2 C3 C4 -56.1(2) . . . . ?
C2 C3 C4 C5 53.7(2) . . . . ?
C3 C4 C5 C6 -55.4(2) . . . . ?
C4 C5 C6 C1 59.1(2) . . . . ?
C13 C1 C6 C5 -175.16(18) . . . . ?
C7 C1 C6 C5 65.4(2) . . . . ?
C2 C1 C6 C5 -57.0(2) . . . . ?
C13 C1 C7 C12 100.3(2) . . . . ?
C6 C1 C7 C12 -137.6(2) . . . . ?
C2 C1 C7 C12 -19.0(3) . . . . ?
C13 C1 C7 C8 -75.9(2) . . . . ?
C6 C1 C7 C8 46.2(3) . . . . ?
C2 C1 C7 C8 164.84(19) . . . . ?
C12 C7 C8 C9 1.5(3) . . . . ?
C1 C7 C8 C9 177.9(2) . . . . ?
C7 C8 C9 C10 -1.1(3) . . . . ?
C8 C9 C10 C11 0.1(3) . . . . ?
C8 C9 C10 O1 -179.88(19) . . . . ?
O1 C10 C11 C12 -179.66(19) . . . . ?
C9 C10 C11 C12 0.3(3) . . . . ?
C10 C11 C12 C7 0.1(3) . . . . ?
C8 C7 C12 C11 -1.0(3) . . . . ?
C1 C7 C12 C11 -177.36(19) . . . . ?
C7 C1 C13 C18 120.6(2) . . . . ?
C6 C1 C13 C18 -0.8(3) . . . . ?
C2 C1 C13 C18 -117.6(2) . . . . ?
C7 C1 C13 C14 -59.5(2) . . . . ?
C6 C1 C13 C14 179.08(19) . . . . ?
C2 C1 C13 C14 62.3(3) . . . . ?
C18 C13 C14 C15 0.3(3) . . . . ?
C1 C13 C14 C15 -179.7(2) . . . . ?
C13 C14 C15 C16 -0.3(3) . . . . ?
C14 C15 C16 C17 0.0(3) . . . . ?
C14 C15 C16 O2 179.3(2) . . . . ?
O2 C16 C17 C18 -178.8(2) . . . . ?
C15 C16 C17 C18 0.5(3) . . . . ?
C14 C13 C18 C17 0.2(3) . . . . ?
C1 C13 C18 C17 -179.9(2) . . . . ?
C16 C17 C18 C13 -0.6(4) . . . . ?
O1G C2G C3G C4G 58.9(4) . . . . ?
C1G C2G C3G C4G -177.2(3) . . . . ?
