# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2002 data_global _journal_coden_Cambridge 182 _journal_volume ? _journal_year ? _journal_page_first ? _publ_requested_journal 'Chemical Communications' loop_ _publ_author_name 'Julius Rebek' 'Byron W. Purse' 'Alexander Shivanyuk' _publ_contact_author_name 'Prof Julius Rebek' _publ_contact_author_address ; Prof Julius Rebek Skaggs Institute for Chemical Biology The Scripps Research Institute 10550 North Torrey Pines Road MB-26 La Jolla CA 92037 UNITED STATES OF AMERICA ; _publ_contact_author_email 'JREBEK@SCRIPPS.EDU' _publ_section_title ; Resorcin[6]arene as a Building Block for Tubular Crystalline State Architectures ; data_bpas1 _database_code_CSD 193890 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C36 H44 O8 S0.44' _chemical_formula_weight 618.96 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' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting rhombohedral _symmetry_space_group_name_H-M R-3 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' _cell_length_a 28.453(5) _cell_length_b 28.453(5) _cell_length_c 10.024(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 7028(3) _cell_formula_units_Z 9 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.316 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2980 _exptl_absorpt_coefficient_mu 0.120 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21034 _diffrn_reflns_av_R_equivalents 0.1108 _diffrn_reflns_av_sigmaI/netI 0.1198 _diffrn_reflns_limit_h_min -37 _diffrn_reflns_limit_h_max 37 _diffrn_reflns_limit_k_min -37 _diffrn_reflns_limit_k_max 37 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.43 _diffrn_reflns_theta_max 28.13 _reflns_number_total 3794 _reflns_number_gt 2279 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.2000P)^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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3794 _refine_ls_number_parameters 188 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2173 _refine_ls_R_factor_gt 0.1632 _refine_ls_wR_factor_ref 0.4641 _refine_ls_wR_factor_gt 0.4352 _refine_ls_goodness_of_fit_ref 1.494 _refine_ls_restrained_S_all 1.494 _refine_ls_shift/su_max 0.428 _refine_ls_shift/su_mean 0.042 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 C6 C 0.1214(2) 0.1203(2) 0.5012(6) 0.0389(14) Uani 1 1 d . . . H6 H 0.0997 0.0854 0.5345 0.047 Uiso 1 1 calc . . . C1 C 0.1179(3) 0.1616(3) 0.5621(6) 0.0408(15) Uani 1 1 d . . . C5 C 0.1549(2) 0.1264(3) 0.3933(7) 0.0411(15) Uani 1 1 d . . . C8 C 0.0574(3) 0.1011(3) 0.7513(7) 0.0450(16) Uani 1 1 d . . . H8A H 0.0377 0.0703 0.6922 0.054 Uiso 1 1 calc R . . H8B H 0.0885 0.0997 0.7857 0.054 Uiso 1 1 calc R . . C2 C 0.1549(3) 0.2152(3) 0.5146(7) 0.0415(15) Uani 1 1 d . . . C4 C 0.1864(3) 0.1790(3) 0.3439(7) 0.0449(16) Uani 1 1 d . . . C3 C 0.1865(3) 0.2217(3) 0.4058(8) 0.0486(17) Uani 1 1 d . . . H3 H 0.2089 0.2565 0.3729 0.058 Uiso 1 1 calc . . . C9 C 0.0208(4) 0.0968(4) 0.8667(9) 0.063(2) Uani 1 1 d . . . H9A H 0.0394 0.1283 0.9225 0.095 Uiso 1 1 calc R . . H9B H 0.0117 0.0649 0.9179 0.095 Uiso 1 1 calc R . . H9C H -0.0117 0.0946 0.8325 0.095 Uiso 1 1 calc R . . C7 C 0.0770(2) 0.1534(3) 0.6723(7) 0.0415(15) Uani 1 1 d . . . CZ3 C 0.1024(2) 0.3100(2) 0.1476(7) 0.0380(14) Uani 1 1 d . . . HZ3A H 0.0910 0.2883 0.0680 0.057 Uiso 1 1 calc R . . HZ3B H 0.1353 0.3434 0.1302 0.057 Uiso 1 1 calc R . . HZ3C H 0.0746 0.3177 0.1750 0.057 Uiso 1 1 calc R . . CZ4 C 0.0689(4) 0.2746(5) 0.3871(12) 0.091(3) Uani 1 1 d . . . HZ4A H 0.0875 0.3055 0.4446 0.136 Uiso 1 1 calc R . . HZ4B H 0.0586 0.2421 0.4371 0.136 Uiso 1 1 calc R . . HZ4C H 0.0371 0.2734 0.3514 0.136 Uiso 1 1 calc R . . O1 O 0.1532(2) 0.25625(18) 0.5800(6) 0.0530(14) Uani 1 1 d . . . H1 H 0.1832 0.2837 0.5765 0.080 Uiso 1 1 calc R . . O2 O 0.2184(2) 0.1860(2) 0.2340(6) 0.0579(14) Uani 1 1 d . . . H2 H 0.2249 0.2139 0.1948 0.087 Uiso 1 1 calc R . . S1 S 0.11198(8) 0.27955(7) 0.2561(2) 0.0630(8) Uani 1 1 d . . . OZ3 O 0.2291(3) 0.2722(3) 0.1015(8) 0.093(2) Uani 1 1 d . . . S2A S 0.22381(17) 0.26764(12) -0.0534(3) 0.0896(14) Uani 0.862(8) 1 d P . . S2 S 0.2192(6) 0.3054(6) 0.0027(14) 0.056(5) Uani 0.138(8) 1 d P . . OZ5 O 0.0792(4) 0.2097(3) 0.2058(13) 0.141(6) Uani 0.97(3) 1 d P . . CT1 C 0.2868(8) 0.3145(6) -0.1213(16) 0.136(6) Uani 1 1 d . . . CT2 C 0.1905(8) 0.3056(7) -0.0953(16) 0.134(6) Uani 1 1 d . . . 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 C6 0.035(3) 0.027(3) 0.047(4) 0.004(3) 0.001(3) 0.010(2) C1 0.046(4) 0.037(3) 0.037(3) 0.004(3) -0.002(3) 0.019(3) C5 0.033(3) 0.040(3) 0.047(4) 0.002(3) -0.001(3) 0.016(3) C8 0.033(3) 0.042(3) 0.055(4) 0.009(3) 0.003(3) 0.015(3) C2 0.033(3) 0.038(3) 0.051(4) -0.003(3) -0.005(3) 0.017(3) C4 0.031(3) 0.048(4) 0.051(4) 0.007(3) 0.003(3) 0.016(3) C3 0.029(3) 0.040(3) 0.068(5) 0.016(3) 0.004(3) 0.010(3) C9 0.061(5) 0.074(5) 0.062(5) 0.021(4) 0.012(4) 0.040(4) C7 0.036(3) 0.039(3) 0.047(4) 0.000(3) 0.000(3) 0.017(3) CZ3 0.038(3) 0.010(2) 0.053(4) 0.001(2) 0.003(3) 0.002(2) CZ4 0.059(5) 0.095(7) 0.112(9) 0.046(7) 0.024(5) 0.034(5) O1 0.050(3) 0.031(2) 0.074(3) -0.004(2) -0.006(3) 0.018(2) O2 0.050(3) 0.052(3) 0.067(3) 0.014(3) 0.014(3) 0.022(2) S1 0.0549(12) 0.0341(10) 0.0875(17) 0.0060(9) -0.0036(10) 0.0130(8) OZ3 0.107(5) 0.069(4) 0.093(5) 0.035(4) 0.020(4) 0.037(4) S2A 0.137(3) 0.0546(17) 0.085(2) 0.0087(14) 0.029(2) 0.0538(18) S2 0.062(9) 0.051(8) 0.047(8) 0.003(6) -0.023(6) 0.023(7) OZ5 0.129(9) 0.049(5) 0.216(13) 0.006(5) -0.054(8) 0.023(5) CT1 0.199(17) 0.088(9) 0.123(11) 0.045(8) 0.071(12) 0.073(10) CT2 0.199(16) 0.135(12) 0.114(11) 0.002(9) 0.017(11) 0.119(13) _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 C6 C1 1.371(9) . ? C6 C5 1.394(9) . ? C1 C2 1.433(9) . ? C1 C7 1.535(9) . ? C5 C4 1.394(9) . ? C5 C7 1.550(9) 11_556 ? C8 C9 1.519(11) . ? C8 C7 1.524(9) . ? C2 O1 1.361(8) . ? C2 C3 1.366(10) . ? C4 C3 1.363(10) . ? C4 O2 1.380(9) . ? C7 C5 1.550(9) 12_556 ? CZ3 S1 1.498(6) . ? CZ4 S1 1.753(11) . ? S1 OZ5 1.795(9) . ? OZ3 S2 1.489(15) . ? OZ3 S2A 1.559(9) . ? S2A S2 1.277(16) . ? S2A CT1 1.750(16) . ? S2A CT2 1.807(16) . ? S2 CT2 1.28(2) . ? S2 CT1 2.19(2) . ? 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 C1 C6 C5 125.2(6) . . ? C6 C1 C2 115.7(6) . . ? C6 C1 C7 124.3(6) . . ? C2 C1 C7 119.9(6) . . ? C6 C5 C4 116.2(6) . . ? C6 C5 C7 120.8(6) . 11_556 ? C4 C5 C7 122.9(6) . 11_556 ? C9 C8 C7 112.1(6) . . ? O1 C2 C3 124.8(6) . . ? O1 C2 C1 115.5(6) . . ? C3 C2 C1 119.6(6) . . ? C3 C4 O2 121.9(6) . . ? C3 C4 C5 120.6(6) . . ? O2 C4 C5 117.5(6) . . ? C4 C3 C2 122.3(6) . . ? C8 C7 C1 113.8(5) . . ? C8 C7 C5 110.5(5) . 12_556 ? C1 C7 C5 108.0(5) . 12_556 ? CZ3 S1 CZ4 105.6(5) . . ? CZ3 S1 OZ5 107.0(4) . . ? CZ4 S1 OZ5 99.6(6) . . ? S2 OZ3 S2A 49.4(6) . . ? S2 S2A OZ3 62.4(7) . . ? S2 S2A CT1 91.5(9) . . ? OZ3 S2A CT1 107.7(7) . . ? S2 S2A CT2 45.1(8) . . ? OZ3 S2A CT2 103.8(6) . . ? CT1 S2A CT2 95.6(8) . . ? S2A S2 CT2 90.0(11) . . ? S2A S2 OZ3 68.1(8) . . ? CT2 S2 OZ3 146.8(14) . . ? S2A S2 CT1 52.9(7) . . ? CT2 S2 CT1 95.0(12) . . ? OZ3 S2 CT1 91.1(9) . . ? S2A CT1 S2 35.6(5) . . ? S2 CT2 S2A 44.9(9) . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 28.13 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 1.150 _refine_diff_density_min -0.846 _refine_diff_density_rms 0.131 #==========================END data_asbp3 _database_code_CSD 193891 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C72 H96 O18' _chemical_formula_weight 1249.49 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 hexagonal _symmetry_space_group_name_H-M R-3 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' _cell_length_a 24.7866(17) _cell_length_b 24.7866(17) _cell_length_c 9.7751(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 5201.0(7) _cell_formula_units_Z 3 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.197 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2016 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16107 _diffrn_reflns_av_R_equivalents 0.0376 _diffrn_reflns_av_sigmaI/netI 0.0281 _diffrn_reflns_limit_h_min -32 _diffrn_reflns_limit_h_max 32 _diffrn_reflns_limit_k_min -32 _diffrn_reflns_limit_k_max 32 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.64 _diffrn_reflns_theta_max 28.02 _reflns_number_total 2796 _reflns_number_gt 2338 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0679P)^2^+4.2186P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2796 _refine_ls_number_parameters 145 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0579 _refine_ls_R_factor_gt 0.0479 _refine_ls_wR_factor_ref 0.1266 _refine_ls_wR_factor_gt 0.1194 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _refine_ls_shift/su_max 0.001 _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 C1 C 0.81286(5) 0.29975(5) 0.23079(12) 0.0144(2) Uani 1 1 d . . . C2 C 0.87400(6) 0.31925(5) 0.19253(12) 0.0158(3) Uani 1 1 d . . . C3 C 0.92399(5) 0.36782(6) 0.26129(13) 0.0186(3) Uani 1 1 d . . . H3 H 0.9646 0.3788 0.2380 0.022 Uiso 1 1 calc . . . C4 C 0.91320(6) 0.39979(6) 0.36440(13) 0.0176(3) Uani 1 1 d . . . C5 C 0.85238(5) 0.38313(5) 0.40301(12) 0.0145(2) Uani 1 1 d . . . C6 C 0.80402(5) 0.33248(5) 0.33666(12) 0.0144(2) Uani 1 1 d . . . H6 H 0.7634 0.3196 0.3642 0.017 Uiso 1 1 calc . . . C7 C 0.75638(5) 0.24699(5) 0.15935(12) 0.0152(3) Uani 1 1 d . . . C7A C 0.72108(6) 0.27246(6) 0.07782(13) 0.0208(3) Uani 1 1 d . . . H7A1 H 0.6847 0.2381 0.0355 0.025 Uiso 1 1 calc R . . H7A2 H 0.7068 0.2933 0.1398 0.025 Uiso 1 1 calc R . . C7B C 0.76171(7) 0.31806(7) -0.03252(14) 0.0298(3) Uani 1 1 d . . . H7B1 H 0.7973 0.3526 0.0092 0.045 Uiso 1 1 calc R . . H7B2 H 0.7381 0.3329 -0.0814 0.045 Uiso 1 1 calc R . . H7B3 H 0.7754 0.2974 -0.0949 0.045 Uiso 1 1 calc R . . C8 C 0.95139(12) 0.41025(12) -0.2051(2) 0.0673(6) Uani 1 1 d . . . H8A H 0.9155 0.3702 -0.1878 0.101 Uiso 1 1 calc R . . H8B H 0.9658 0.4114 -0.2968 0.101 Uiso 1 1 calc R . . H8C H 0.9404 0.4421 -0.1942 0.101 Uiso 1 1 calc R . . C9 C 1.00159(8) 0.42122(7) -0.10678(16) 0.0334(4) Uani 1 1 d . . . C10 C 1.06083(9) 0.48227(8) -0.1133(2) 0.0476(5) Uani 1 1 d . . . H10A H 1.0877 0.4848 -0.0397 0.071 Uiso 1 1 calc R . . H10B H 1.0518 0.5155 -0.1052 0.071 Uiso 1 1 calc R . . H10C H 1.0811 0.4857 -0.1991 0.071 Uiso 1 1 calc R . . O1 O 0.88501(4) 0.29055(4) 0.08327(9) 0.0199(2) Uani 1 1 d . . . H1 H 0.9188 0.3147 0.0488 0.030 Uiso 1 1 calc R . . O2 O 0.96010(4) 0.44980(4) 0.42982(11) 0.0265(2) Uani 1 1 d . . . H2 H 0.9930 0.4501 0.4178 0.040 Uiso 1 1 calc R . . O3 O 0.99488(5) 0.38199(5) -0.02319(12) 0.0373(3) Uani 1 1 d . . . H1X H 0.7717(7) 0.2279(7) 0.0944(15) 0.019(4) Uiso 1 1 d . . . 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 C1 0.0154(6) 0.0117(5) 0.0159(5) 0.0023(4) 0.0003(4) 0.0066(4) C2 0.0182(6) 0.0130(5) 0.0172(6) 0.0019(4) 0.0029(4) 0.0086(5) C3 0.0125(5) 0.0190(6) 0.0245(6) -0.0002(5) 0.0018(4) 0.0081(5) C4 0.0154(6) 0.0146(6) 0.0217(6) -0.0017(4) -0.0026(4) 0.0065(5) C5 0.0162(6) 0.0132(5) 0.0162(5) 0.0015(4) -0.0002(4) 0.0090(5) C6 0.0135(5) 0.0138(5) 0.0170(6) 0.0024(4) 0.0008(4) 0.0076(4) C7 0.0149(5) 0.0140(5) 0.0157(6) 0.0002(4) 0.0015(4) 0.0063(5) C7A 0.0203(6) 0.0194(6) 0.0201(6) 0.0013(5) -0.0041(5) 0.0079(5) C7B 0.0311(8) 0.0272(7) 0.0240(7) 0.0073(5) -0.0041(6) 0.0093(6) C8 0.0794(16) 0.0625(14) 0.0536(13) -0.0003(11) -0.0194(11) 0.0307(13) C9 0.0399(9) 0.0356(8) 0.0281(7) 0.0037(6) 0.0141(6) 0.0215(7) C10 0.0428(10) 0.0385(9) 0.0597(12) 0.0185(8) 0.0234(9) 0.0189(8) O1 0.0180(4) 0.0165(4) 0.0228(5) -0.0021(3) 0.0066(3) 0.0068(4) O2 0.0133(4) 0.0247(5) 0.0382(6) -0.0149(4) -0.0045(4) 0.0072(4) O3 0.0340(6) 0.0344(6) 0.0373(6) 0.0119(5) 0.0141(5) 0.0125(5) _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 C1 C2 1.3919(16) . ? C1 C6 1.3982(16) . ? C1 C7 1.5254(16) . ? C2 O1 1.3839(14) . ? C2 C3 1.3946(17) . ? C3 C4 1.3881(17) . ? C4 O2 1.3624(15) . ? C4 C5 1.4012(16) . ? C5 C6 1.3888(16) . ? C5 C7 1.5206(16) 18_545 ? C7 C5 1.5207(16) 17 ? C7 C7A 1.5337(17) . ? C7A C7B 1.5222(18) . ? C8 C9 1.486(3) . ? C9 O3 1.2163(19) . ? C9 C10 1.493(2) . ? 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 C2 C1 C6 117.17(11) . . ? C2 C1 C7 123.22(10) . . ? C6 C1 C7 119.56(10) . . ? O1 C2 C1 119.28(10) . . ? O1 C2 C3 119.82(10) . . ? C1 C2 C3 120.89(11) . . ? C4 C3 C2 120.08(11) . . ? O2 C4 C3 122.68(11) . . ? O2 C4 C5 116.39(11) . . ? C3 C4 C5 120.89(11) . . ? C6 C5 C4 117.11(11) . . ? C6 C5 C7 123.78(10) . 18_545 ? C4 C5 C7 119.01(10) . 18_545 ? C5 C6 C1 123.74(11) . . ? C5 C7 C1 109.47(9) 17 . ? C5 C7 C7A 113.97(10) 17 . ? C1 C7 C7A 110.66(10) . . ? C7B C7A C7 111.84(11) . . ? O3 C9 C8 121.40(17) . . ? O3 C9 C10 120.73(16) . . ? C8 C9 C10 117.87(17) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 28.02 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.403 _refine_diff_density_min -0.201 _refine_diff_density_rms 0.050