# Electronic Supplementary Material for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2008

data_global

_journal_coden_Cambridge         1350

loop_
_publ_author_name
'Hong Su.'

_publ_contact_author_name        'Luigi Nassimbeni'
_publ_contact_author_email       LUIGI.NASSIMBENI@UCT.AC.ZA

_publ_section_title              
;
Selectivity of butnaol isomers by enclathration
;

# Attachment '1BuOH.CIF'

data_H1BuOH
_database_code_depnum_ccdc_archive 'CCDC 696305'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
1,1-bis(4-hydroxyphenyl)cyclohexane 1-butanol clathrate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H30 O3'
_chemical_formula_weight         342.46

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.2403(3)
_cell_length_b                   10.7398(4)
_cell_length_c                   14.7067(7)
_cell_angle_alpha                98.713(3)
_cell_angle_beta                 91.987(2)
_cell_angle_gamma                101.320(3)
_cell_volume                     953.20(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.193
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             372
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   none

_exptl_special_details           
;
Half sphere of data collected using COLLECT strategy (Nonius, 2000).
Crystal to detector distance = 32mm; combination of φ and ω scans of
1.2°, 40s per °, 2 iterations.
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius Kappa CCD diffractometer'
_diffrn_measurement_method       '1.2° φ scans and ω scans'
_diffrn_reflns_number            6713
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_sigmaI/netI    0.0537
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.22
_diffrn_reflns_theta_max         25.68
_reflns_number_total             3616
_reflns_number_gt                2400
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'COLLECT program (Nonius, 2000)'
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'X-Seed (Barbour, 2001)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2001)'

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0635P)²+0.1711P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.032(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3616
_refine_ls_number_parameters     248
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0843
_refine_ls_R_factor_gt           0.0470
_refine_ls_wR_factor_ref         0.1320
_refine_ls_wR_factor_gt          0.1122
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

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_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_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

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.68
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.424
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.043

# Attachment '2BuOH.CIF'

data_H2BuOH
_database_code_depnum_ccdc_archive 'CCDC 696306'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
1,1-bis(4-hydroxyphenyl)cyclohexane 2-butanol clathrate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H30 O3'
_chemical_formula_weight         342.46

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/n

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'

_cell_length_a                   6.2995(10)
_cell_length_b                   28.658(2)
_cell_length_c                   10.9868(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.579(3)
_cell_angle_gamma                90.00
_cell_volume                     1935.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.175
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             744
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   none

_exptl_special_details           
;
Half sphere of data collected using COLLECT strategy (Nonius, 2000).
Crystal to detector distance = 30mm; combination of φ and ω scans of
1.2°, 50s per °, 2 iterations.
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius Kappa CCD diffractometer'
_diffrn_measurement_method       '1.2° φ scans and ω scans'
_diffrn_reflns_number            10655
_diffrn_reflns_av_R_equivalents  0.0663
_diffrn_reflns_av_sigmaI/netI    0.0780
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.84
_diffrn_reflns_theta_max         25.36
_reflns_number_total             3532
_reflns_number_gt                2105
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'COLLECT program (Nonius, 2000)'
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'X-Seed (Barbour, 2001)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2001)'

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1002P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.008(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3532
_refine_ls_number_parameters     239
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1080
_refine_ls_R_factor_gt           0.0564
_refine_ls_wR_factor_ref         0.1720
_refine_ls_wR_factor_gt          0.1433
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

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_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_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) . . . . ?

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

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.36
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.467
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.060

# Attachment 'iosBuOH1.CIF'

data_HisoBuOH
_database_code_depnum_ccdc_archive 'CCDC 696307'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
1,1-bis(4-hydroxyphenyl)cyclohexane iso-butanol clathrate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H30 O3'
_chemical_formula_weight         342.46

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.2259(2)
_cell_length_b                   10.8829(6)
_cell_length_c                   15.2046(8)
_cell_angle_alpha                94.029(2)
_cell_angle_beta                 100.875(3)
_cell_angle_gamma                101.498(3)
_cell_volume                     985.15(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)

_exptl_crystal_description       needle
_exptl_crystal_colour            P-1
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.154
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             372
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_type   none

_exptl_special_details           
;
Half sphere of data collected using COLLECT strategy (Nonius, 2000).
Crystal to detector distance = 30mm; combination of φ and ω scans of
1.2°, 60s per °, 2 iterations.
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius Kappa CCD diffractometer'
_diffrn_measurement_method       '1.2° φ scans and ω scans'
_diffrn_reflns_number            3719
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0489
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.23
_diffrn_reflns_theta_max         25.67
_reflns_number_total             3719
_reflns_number_gt                2481
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'COLLECT program (Nonius, 2000)'
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'X-Seed (Barbour, 2001)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2001)'

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0553P)²+0.1753P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.016(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3719
_refine_ls_number_parameters     239
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0839
_refine_ls_R_factor_gt           0.0443
_refine_ls_wR_factor_ref         0.1202
_refine_ls_wR_factor_gt          0.1022
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

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_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_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

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.67
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.040


