# 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 \f and \w 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\% \f scans and \w 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 F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ 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/[\s^2^(Fo^2^)+(0.0635P)^2^+0.1711P] where P=(Fo^2^+2Fc^2^)/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+0.001xFc^2^\l^3^/sin(2\q)]^-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 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0390(9) 0.0287(7) 0.0398(9) 0.0160(6) 0.0124(7) 0.0104(6) O2 0.0382(8) 0.0277(7) 0.0326(8) -0.0017(6) -0.0014(6) 0.0098(6) C1 0.0209(9) 0.0214(8) 0.0254(10) 0.0046(7) 0.0034(7) 0.0056(7) C2 0.0227(10) 0.0253(9) 0.0282(11) 0.0026(8) 0.0012(8) 0.0049(7) C3 0.0297(11) 0.0314(10) 0.0250(10) 0.0057(8) -0.0006(8) 0.0061(8) C4 0.0360(11) 0.0334(10) 0.0311(11) 0.0117(9) 0.0084(9) 0.0091(9) C5 0.0248(10) 0.0339(10) 0.0356(12) 0.0109(9) 0.0082(8) 0.0069(8) C6 0.0246(10) 0.0265(9) 0.0302(11) 0.0052(8) 0.0041(8) 0.0073(8) C7 0.0234(10) 0.0221(9) 0.0233(10) 0.0025(7) 0.0011(7) 0.0045(7) C8 0.0247(10) 0.0246(9) 0.0311(11) 0.0070(8) 0.0015(8) 0.0069(8) C9 0.0235(10) 0.0288(9) 0.0302(11) 0.0055(8) 0.0050(8) 0.0059(8) C10 0.0304(10) 0.0219(8) 0.0246(10) 0.0040(7) 0.0027(8) 0.0022(8) C11 0.0314(11) 0.0274(9) 0.0377(12) 0.0111(9) 0.0064(9) 0.0124(8) C12 0.0258(10) 0.0280(9) 0.0324(11) 0.0074(8) 0.0067(8) 0.0084(8) C13 0.0211(9) 0.0223(8) 0.0249(10) 0.0073(7) 0.0032(7) 0.0038(7) C14 0.0230(10) 0.0269(9) 0.0279(10) 0.0054(8) -0.0005(8) 0.0053(8) C15 0.0265(10) 0.0278(9) 0.0311(11) 0.0082(8) 0.0022(8) 0.0104(8) C16 0.0306(10) 0.0221(9) 0.0232(10) 0.0051(8) 0.0053(8) 0.0050(8) C17 0.0282(10) 0.0305(10) 0.0276(11) 0.0041(8) -0.0042(8) 0.0041(8) C18 0.0260(10) 0.0275(9) 0.0338(11) 0.0068(8) -0.0002(8) 0.0098(8) O1G 0.0360(9) 0.0457(9) 0.0347(9) 0.0094(7) 0.0064(7) 0.0024(7) C1G 0.0520(15) 0.0457(13) 0.0359(13) 0.0018(10) 0.0099(11) 0.0015(11) C2G1 0.0586(16) 0.0632(15) 0.0356(13) 0.0096(11) 0.0083(11) 0.0188(12) C3G1 0.058(2) 0.055(2) 0.0402(19) 0.0219(16) 0.0171(16) 0.0134(17) C4G1 0.088(2) 0.115(3) 0.066(2) 0.0086(19) 0.0087(17) 0.051(2) C3G2 0.057(6) 0.053(6) 0.041(6) 0.009(5) 0.000(5) 0.017(5) C4G2 0.088(2) 0.115(3) 0.066(2) 0.0086(19) 0.0087(17) 0.051(2) C2G2 0.0586(16) 0.0632(15) 0.0356(13) 0.0096(11) 0.0083(11) 0.0188(12) _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 \f and \w 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\% \f scans and \w 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 F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ 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/[\s^2^(Fo^2^)+(0.1002P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/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+0.001xFc^2^\l^3^/sin(2\q)]^-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 . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0442(10) 0.0435(11) 0.0338(9) 0.0082(8) 0.0140(8) 0.0058(8) O2 0.0391(10) 0.0528(11) 0.0356(10) -0.0124(8) 0.0112(8) -0.0100(8) C1 0.0233(12) 0.0370(14) 0.0275(12) -0.0010(10) 0.0066(10) -0.0003(10) C2 0.0282(12) 0.0367(14) 0.0316(13) 0.0019(11) 0.0062(10) 0.0000(10) C3 0.0383(14) 0.0342(14) 0.0380(14) -0.0020(11) 0.0087(11) 0.0026(11) C4 0.0394(14) 0.0418(15) 0.0407(14) -0.0053(12) 0.0082(11) -0.0067(11) C5 0.0297(12) 0.0455(15) 0.0383(14) -0.0044(12) 0.0059(11) -0.0071(11) C6 0.0289(12) 0.0394(14) 0.0311(13) 0.0001(11) 0.0066(10) -0.0036(11) C7 0.0239(12) 0.0330(13) 0.0261(12) -0.0045(10) 0.0046(10) -0.0009(10) C8 0.0294(13) 0.0391(14) 0.0324(13) -0.0016(11) 0.0120(10) 0.0031(11) C9 0.0320(13) 0.0343(14) 0.0332(13) 0.0008(11) 0.0059(10) 0.0073(10) C10 0.0346(13) 0.0308(13) 0.0262(12) -0.0003(10) 0.0064(10) -0.0014(10) C11 0.0279(12) 0.0390(14) 0.0313(13) -0.0028(11) 0.0113(10) 0.0026(11) C12 0.0268(12) 0.0352(13) 0.0310(13) 0.0003(11) 0.0044(10) 0.0034(10) C13 0.0269(12) 0.0330(13) 0.0258(12) 0.0019(10) 0.0054(10) -0.0005(10) C14 0.0301(12) 0.0428(14) 0.0298(12) -0.0013(11) 0.0092(10) -0.0006(11) C15 0.0292(13) 0.0428(15) 0.0352(13) -0.0011(11) 0.0055(11) -0.0059(11) C16 0.0329(13) 0.0360(13) 0.0248(12) -0.0033(10) 0.0047(10) -0.0027(11) C17 0.0326(13) 0.0485(16) 0.0287(13) -0.0034(11) 0.0104(11) -0.0022(11) C18 0.0287(12) 0.0440(15) 0.0297(13) -0.0013(11) 0.0059(10) -0.0047(11) O1G 0.0407(12) 0.0448(12) 0.0979(16) 0.0197(11) -0.0064(11) -0.0059(9) C1G 0.095(3) 0.087(3) 0.073(2) -0.006(2) 0.029(2) -0.008(2) C2G 0.0529(18) 0.057(2) 0.081(2) 0.0252(17) 0.0004(16) 0.0054(15) C3G 0.093(3) 0.053(2) 0.080(2) 0.0129(17) 0.022(2) -0.0047(18) C4G 0.096(3) 0.092(3) 0.089(3) 0.027(2) 0.042(2) 0.019(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 1.381(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 \f and \w 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\% \f scans and \w 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 F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ 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/[\s^2^(Fo^2^)+(0.0553P)^2^+0.1753P] where P=(Fo^2^+2Fc^2^)/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+0.001xFc^2^\l^3^/sin(2\q)]^-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 . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0390(7) 0.0295(7) 0.0372(7) 0.0104(6) 0.0096(6) 0.0125(6) O2 0.0322(7) 0.0277(8) 0.0478(8) -0.0059(6) -0.0018(6) 0.0070(6) C1 0.0214(8) 0.0243(9) 0.0276(9) 0.0036(7) 0.0051(6) 0.0057(7) C2 0.0228(9) 0.0294(10) 0.0342(10) 0.0044(8) 0.0054(7) 0.0086(7) C3 0.0217(9) 0.0315(10) 0.0402(10) 0.0003(8) 0.0025(7) 0.0051(7) C4 0.0317(10) 0.0371(11) 0.0337(10) -0.0024(8) 0.0007(8) 0.0070(8) C5 0.0300(9) 0.0347(11) 0.0274(9) 0.0018(8) 0.0073(7) 0.0084(8) C6 0.0242(8) 0.0274(10) 0.0293(9) 0.0060(8) 0.0064(7) 0.0061(7) C13 0.0236(8) 0.0244(9) 0.0257(9) 0.0064(7) 0.0065(6) 0.0060(7) C18 0.0225(8) 0.0286(10) 0.0356(10) 0.0038(8) 0.0031(7) 0.0070(7) C17 0.0284(9) 0.0271(10) 0.0383(10) 0.0013(8) 0.0036(7) 0.0118(8) C16 0.0301(9) 0.0239(10) 0.0304(9) 0.0036(8) 0.0029(7) 0.0046(7) C15 0.0232(9) 0.0303(10) 0.0351(10) 0.0031(8) 0.0030(7) 0.0062(7) C14 0.0260(9) 0.0274(10) 0.0364(10) 0.0037(8) 0.0064(7) 0.0107(7) C7 0.0222(8) 0.0221(9) 0.0264(9) -0.0004(7) 0.0034(6) 0.0035(7) C12 0.0245(9) 0.0276(10) 0.0318(9) 0.0053(8) 0.0095(7) 0.0067(7) C11 0.0268(9) 0.0267(10) 0.0329(10) 0.0008(8) 0.0052(7) 0.0105(7) C10 0.0293(9) 0.0206(9) 0.0265(9) 0.0028(7) 0.0020(7) 0.0056(7) C9 0.0332(10) 0.0302(10) 0.0311(10) 0.0048(8) 0.0128(7) 0.0099(8) C8 0.0268(9) 0.0290(10) 0.0358(10) 0.0054(8) 0.0099(7) 0.0120(8) O1G 0.0366(8) 0.0605(10) 0.0404(8) 0.0175(7) 0.0007(6) -0.0023(7) C1G 0.0592(13) 0.0462(13) 0.0342(11) 0.0065(10) 0.0076(9) 0.0039(10) C2G 0.0693(15) 0.0410(13) 0.0375(11) 0.0015(10) 0.0059(10) 0.0071(11) C3G 0.143(3) 0.0514(17) 0.0468(15) 0.0141(12) 0.0139(15) 0.0048(16) C4G 0.102(2) 0.096(2) 0.097(2) 0.0233(19) 0.0238(18) 0.0547(19) _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