#------------------------------------------------------------------------------
#$Date: 2016-03-26 16:21:06 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180334 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/03/7200311.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_7200311
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 1-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                98.713(3)
_cell_angle_beta                 91.987(2)
_cell_angle_gamma                101.320(3)
_cell_formula_units_Z            2
_cell_length_a                   6.2403(3)
_cell_length_b                   10.7398(4)
_cell_length_c                   14.7067(7)
_cell_measurement_temperature    173(2)
_cell_volume                     953.20(7)
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0291
_diffrn_reflns_av_sigmaI/netI    0.0537
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6713
_diffrn_reflns_theta_full        25.68
_diffrn_reflns_theta_max         25.68
_diffrn_reflns_theta_min         2.22
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.193
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       needle
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.424
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.032(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3616
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0843
_refine_ls_R_factor_gt           0.0470
_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)+(0.0635P)²+0.1711P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1122
_refine_ls_wR_factor_ref         0.1320
_reflns_number_gt                2400
_reflns_number_total             3616
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b812887a.txt
_cod_data_source_block           H1BuOH
_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               7200311
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 0.5161(2) 0.83127(12) 0.81768(10) 0.0340(4) Uani 1 1 d . . .
H1 H 0.386(4) 0.844(2) 0.8506(18) 0.072(8) Uiso 1 1 d . . .
O2 O 0.8055(2) 1.68606(12) 0.85331(9) 0.0331(4) Uani 1 1 d . . .
H2 H 0.695(4) 1.731(2) 0.8432(17) 0.063(8) Uiso 1 1 d . . .
C1 C 0.7736(3) 1.22399(15) 0.59600(12) 0.0223(4) Uani 1 1 d . . .
C2 C 0.6033(3) 1.20116(16) 0.51280(12) 0.0256(4) Uani 1 1 d . . .
H2A H 0.5921 1.1127 0.4793 0.031 Uiso 1 1 calc R . .
H2B H 0.4583 1.2073 0.5362 0.031 Uiso 1 1 calc R . .
C3 C 0.6580(3) 1.29602(17) 0.44502(13) 0.0286(4) Uani 1 1 d . . .
H3A H 0.5475 1.2723 0.3921 0.034 Uiso 1 1 calc R . .
H3B H 0.6517 1.3837 0.4759 0.034 Uiso 1 1 calc R . .
C4 C 0.8850(3) 1.29600(18) 0.41017(13) 0.0324(5) Uani 1 1 d . . .
H4A H 0.9220 1.3640 0.3714 0.039 Uiso 1 1 calc R . .
H4B H 0.8856 1.2121 0.3716 0.039 Uiso 1 1 calc R . .
C5 C 1.0566(3) 1.31975(18) 0.49083(13) 0.0306(5) Uani 1 1 d . . .
H5A H 1.0669 1.4075 0.5255 0.037 Uiso 1 1 calc R . .
H5B H 1.2014 1.3143 0.4670 0.037 Uiso 1 1 calc R . .
C6 C 0.9974(3) 1.22128(16) 0.55538(13) 0.0267(4) Uani 1 1 d . . .
H6A H 1.1123 1.2386 0.6064 0.032 Uiso 1 1 calc R . .
H6B H 0.9947 1.1342 0.5211 0.032 Uiso 1 1 calc R . .
C7 C 0.7074(3) 1.11575(15) 0.65398(12) 0.0231(4) Uani 1 1 d . . .
C8 C 0.5069(3) 1.10270(16) 0.69450(13) 0.0263(4) Uani 1 1 d . . .
H8 H 0.4138 1.1602 0.6847 0.032 Uiso 1 1 calc R . .
C9 C 0.4386(3) 1.00943(17) 0.74838(13) 0.0273(4) Uani 1 1 d . . .
H9 H 0.3002 1.0025 0.7743 0.033 Uiso 1 1 calc R . .
C10 C 0.5746(3) 0.92594(16) 0.76417(13) 0.0260(4) Uani 1 1 d . . .
C11 C 0.7741(3) 0.93616(17) 0.72519(13) 0.0306(5) Uani 1 1 d . . .
H11 H 0.8672 0.8789 0.7357 0.037 Uiso 1 1 calc R . .
C12 C 0.8391(3) 1.02990(16) 0.67057(13) 0.0279(4) Uani 1 1 d . . .
H12 H 0.9766 1.0355 0.6440 0.034 Uiso 1 1 calc R . .
C13 C 0.7811(3) 1.35226(16) 0.66081(12) 0.0225(4) Uani 1 1 d . . .
C14 C 0.6176(3) 1.42345(16) 0.65918(13) 0.0259(4) Uani 1 1 d . . .
H14 H 0.4990 1.3953 0.6137 0.031 Uiso 1 1 calc R . .
C15 C 0.6229(3) 1.53433(16) 0.72206(13) 0.0274(4) Uani 1 1 d . . .
H15 H 0.5090 1.5810 0.7194 0.033 Uiso 1 1 calc R . .
C16 C 0.7941(3) 1.57695(16) 0.78865(12) 0.0251(4) Uani 1 1 d . . .
C17 C 0.9584(3) 1.50796(17) 0.79257(13) 0.0293(4) Uani 1 1 d . . .
H17 H 1.0763 1.5365 0.8383 0.035 Uiso 1 1 calc R . .
C18 C 0.9504(3) 1.39747(17) 0.72973(13) 0.0283(4) Uani 1 1 d . . .
H18 H 1.0637 1.3506 0.7334 0.034 Uiso 1 1 calc R . .
O1G O 0.1837(2) 0.85928(14) 0.91789(10) 0.0392(4) Uani 1 1 d . B .
H1G H 0.064(5) 0.797(3) 0.8965(19) 0.079(9) Uiso 1 1 d . . .
C1G C 0.1935(4) 0.8796(2) 1.01683(15) 0.0460(6) Uani 1 1 d . . .
H1G1 H 0.0540 0.9012 1.0375 0.055 Uiso 1 1 calc R A 1
H1G2 H 0.3124 0.9543 1.0404 0.055 Uiso 1 1 calc R A 1
C2G1 C 0.2319(4) 0.7674(2) 1.05788(16) 0.0513(6) Uani 0.75 1 d P B 1
H2G1 H 0.1264 0.6888 1.0289 0.062 Uiso 0.75 1 calc PR B 1
H2G2 H 0.2116 0.7816 1.1248 0.062 Uiso 0.75 1 calc PR B 1
C3G1 C 0.4740(6) 0.7508(3) 1.0408(2) 0.0488(8) Uani 0.75 1 d P B 1
H3G1 H 0.4848 0.7234 0.9740 0.059 Uiso 0.75 1 calc PR B 1
H3G2 H 0.5747 0.8352 1.0591 0.059 Uiso 0.75 1 calc PR B 1
C4G1 C 0.5436(6) 0.6593(3) 1.0902(2) 0.0860(10) Uani 0.75 1 d P B 1
H4G1 H 0.6945 0.6537 1.0768 0.129 Uiso 0.75 1 calc PR B 1
H4G2 H 0.4474 0.5747 1.0711 0.129 Uiso 0.75 1 calc PR B 1
H4G3 H 0.5366 0.6866 1.1565 0.129 Uiso 0.75 1 calc PR B 1
C3G2 C 0.3516(17) 0.6623(10) 1.0266(6) 0.050(2) Uani 0.25 1 d P B 2
H3G3 H 0.4041 0.6726 0.9649 0.060 Uiso 0.25 1 calc PR B 2
H3G4 H 0.2476 0.5785 1.0202 0.060 Uiso 0.25 1 calc PR B 2
C4G2 C 0.5436(6) 0.6593(3) 1.0902(2) 0.0860(10) Uani 0.25 1 d P B 2
H4G4 H 0.6131 0.5883 1.0652 0.129 Uiso 0.25 1 calc PR B 2
H4G5 H 0.4931 0.6467 1.1511 0.129 Uiso 0.25 1 calc PR B 2
H4G6 H 0.6499 0.7408 1.0957 0.129 Uiso 0.25 1 calc PR B 2
C2G2 C 0.2319(4) 0.7674(2) 1.05788(16) 0.0513(6) Uani 0.25 1 d P B 2
H2G3 H 0.0831 0.7211 1.0678 0.062 Uiso 0.25 1 calc PR B 2
H2G4 H 0.3002 0.8054 1.1202 0.062 Uiso 0.25 1 calc PR B 2
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
C6 C1 C13 110.64(14) . . ?
C6 C1 C7 111.89(13) . . ?
C13 C1 C7 106.66(14) . . ?
C6 C1 C2 106.41(15) . . ?
C13 C1 C2 113.02(14) . . ?
C7 C1 C2 108.28(14) . . ?
C3 C2 C1 114.02(14) . . ?
C4 C3 C2 111.24(14) . . ?
C3 C4 C5 110.60(16) . . ?
C4 C5 C6 111.00(15) . . ?
C5 C6 C1 112.71(14) . . ?
C12 C7 C8 116.79(16) . . ?
C12 C7 C1 123.74(16) . . ?
C8 C7 C1 119.45(14) . . ?
C9 C8 C7 122.60(16) . . ?
C8 C9 C10 119.16(17) . . ?
O1 C10 C11 118.34(16) . . ?
O1 C10 C9 121.88(17) . . ?
C11 C10 C9 119.78(16) . . ?
C10 C11 C12 120.20(16) . . ?
C11 C12 C7 121.47(17) . . ?
C14 C13 C18 116.61(16) . . ?
C14 C13 C1 123.34(15) . . ?
C18 C13 C1 119.90(15) . . ?
C15 C14 C13 121.82(17) . . ?
C16 C15 C14 119.99(16) . . ?
O2 C16 C15 122.12(16) . . ?
O2 C16 C17 118.24(16) . . ?
C15 C16 C17 119.64(17) . . ?
C18 C17 C16 119.71(17) . . ?
C17 C18 C13 122.22(17) . . ?
O1G C1G C2G1 114.05(19) . . ?
C1G C2G1 C3G1 108.2(2) . . ?
C4G1 C3G1 C2G1 113.6(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 1.380(2) . ?
O2 C16 1.381(2) . ?
C1 C6 1.542(2) . ?
C1 C13 1.543(2) . ?
C1 C7 1.544(2) . ?
C1 C2 1.550(2) . ?
C2 C3 1.531(2) . ?
C3 C4 1.523(3) . ?
C4 C5 1.527(3) . ?
C5 C6 1.527(2) . ?
C7 C12 1.392(2) . ?
C7 C8 1.396(2) . ?
C8 C9 1.382(2) . ?
C9 C10 1.388(2) . ?
C10 C11 1.380(3) . ?
C11 C12 1.390(2) . ?
C13 C14 1.391(2) . ?
C13 C18 1.398(3) . ?
C14 C15 1.387(2) . ?
C15 C16 1.382(3) . ?
C16 C17 1.382(3) . ?
C17 C18 1.381(3) . ?
O1G C1G 1.436(3) . ?
C1G C2G1 1.482(3) . ?
C2G1 C3G1 1.580(4) . ?
C3G1 C4G1 1.430(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 0.98(3) 1.65(3) 2.624(2) 172(2) .
O2 H2 O1 0.94(3) 1.76(3) 2.6940(19) 172(2) 1_565
O1G H1G O2 0.91(3) 1.84(3) 2.742(2) 174(3) 1_445
