# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2003 data_global _journal_name_full 'Organic & Biomolecular Chemistry' _journal_coden_Cambridge ? _journal_volume ? _journal_year ? _journal_page_first ? loop_ _publ_author_name 'Kenneth W. Muir' 'Santiago de la Moya Cerero' 'Amelia Garcia Fraile' 'Antonio Garcia Martinez' 'David G. Morris' ; K.Ryder ; 'Enrique Teso Vilar' _publ_contact_author_name 'Dr Kenneth W. Muir' _publ_contact_author_address ; Dr Kenneth W. Muir Chemistry Department Glasgow University University Avenue Glasgow G12 8QQ UNITED KINGDOM ; _publ_contact_author_email KEN@CHEM.GLA.AC.UK _publ_section_title ; Self -recognition and hydrogen bonding by polycyclic bridgehead monoalcohols ; data_2 _database_code_CSD 195489 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'Compound X' _chemical_melting_point ? _chemical_formula_moiety 'C9 H14 O2' _chemical_formula_sum 'C9 H14 O2' _chemical_formula_weight 154.20 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 'P 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 6.1182(3) _cell_length_b 6.6921(4) _cell_length_c 10.1810(5) _cell_angle_alpha 90.00 _cell_angle_beta 94.019(3) _cell_angle_gamma 90.00 _cell_volume 415.82(4) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1207 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 30.034 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.232 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 168 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 KappaCCD _diffrn_measurement_method 'CCD; rotation images; thick slices' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4157 _diffrn_reflns_av_R_equivalents 0.036 _diffrn_reflns_av_sigmaI/netI 0.0556 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.34 _diffrn_reflns_theta_max 30.02 _reflns_number_total 2340 _reflns_number_gt 2043 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0329P)^2^+0.0789P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.2(11) _refine_ls_number_reflns 2340 _refine_ls_number_parameters 108 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0541 _refine_ls_R_factor_gt 0.0425 _refine_ls_wR_factor_ref 0.0929 _refine_ls_wR_factor_gt 0.0878 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _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 C1 C 0.3583(2) 0.9663(2) 0.63182(13) 0.0140(3) Uani 1 1 d . . . C2 C 0.2837(2) 0.7801(2) 0.70031(14) 0.0145(3) Uani 1 1 d . . . C3 C 0.1649(2) 0.8475(2) 0.81998(14) 0.0156(3) Uani 1 1 d . . . C4 C 0.1847(2) 1.0774(2) 0.80659(14) 0.0159(3) Uani 1 1 d . . . H4 H 0.1673 1.1520 0.8903 0.0220(17) Uiso 1 1 calc R . . C5 C 0.0369(2) 1.1540(2) 0.68869(14) 0.0179(3) Uani 1 1 d . . . H5A H 0.0360 1.3018 0.6853 0.0220(17) Uiso 1 1 calc R . . H5B H -0.1153 1.1052 0.6926 0.0220(17) Uiso 1 1 calc R . . C6 C 0.1461(2) 1.0642(2) 0.56935(13) 0.0162(3) Uani 1 1 d . . . H6A H 0.1805 1.1697 0.5059 0.0220(17) Uiso 1 1 calc R . . H6B H 0.0499 0.9634 0.5236 0.0220(17) Uiso 1 1 calc R . . C7 C 0.4121(2) 1.1026(2) 0.75157(13) 0.0161(3) Uani 1 1 d . . . H7A H 0.4429 1.2422 0.7265 0.0220(17) Uiso 1 1 calc R . . H7B H 0.5328 1.0501 0.8117 0.0220(17) Uiso 1 1 calc R . . C8 C 0.2909(3) 0.7702(3) 0.94568(14) 0.0224(3) Uani 1 1 d . . . H8A H 0.2991 0.6240 0.9426 0.029(2) Uiso 1 1 calc R . . H8B H 0.2145 0.8111 1.0227 0.029(2) Uiso 1 1 calc R . . H8C H 0.4393 0.8260 0.9519 0.029(2) Uiso 1 1 calc R . . C9 C -0.0685(2) 0.7639(2) 0.81375(14) 0.0203(3) Uani 1 1 d . . . H9A H -0.1439 0.7973 0.7285 0.029(2) Uiso 1 1 calc R . . H9B H -0.1480 0.8225 0.8846 0.029(2) Uiso 1 1 calc R . . H9C H -0.0629 0.6184 0.8242 0.029(2) Uiso 1 1 calc R . . O1 O 0.52033(19) 0.91829(17) 0.54652(11) 0.0203(2) Uani 1 1 d . . . O2 O 0.31469(17) 0.60916(16) 0.66773(10) 0.0220(3) Uani 1 1 d . . . H1 H 0.538(4) 1.014(4) 0.497(3) 0.045(7) 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 0.0160(6) 0.0129(6) 0.0133(6) 0.0005(5) 0.0038(5) 0.0001(6) C2 0.0148(6) 0.0147(6) 0.0141(6) 0.0002(5) 0.0018(5) 0.0013(6) C3 0.0165(7) 0.0162(6) 0.0147(7) 0.0022(6) 0.0043(5) 0.0015(6) C4 0.0186(7) 0.0149(7) 0.0141(6) -0.0022(5) 0.0013(5) 0.0015(6) C5 0.0181(7) 0.0158(7) 0.0201(7) 0.0018(5) 0.0034(6) 0.0038(5) C6 0.0172(7) 0.0154(7) 0.0157(7) 0.0019(5) -0.0010(5) -0.0003(5) C7 0.0175(7) 0.0145(6) 0.0162(7) -0.0004(5) 0.0007(5) -0.0011(6) C8 0.0250(8) 0.0258(8) 0.0168(7) 0.0054(6) 0.0031(6) 0.0041(7) C9 0.0209(7) 0.0202(7) 0.0205(7) 0.0037(6) 0.0064(6) -0.0005(6) O1 0.0237(6) 0.0193(6) 0.0191(5) 0.0039(4) 0.0107(4) 0.0037(4) O2 0.0293(6) 0.0139(5) 0.0239(6) -0.0003(4) 0.0103(5) 0.0020(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 O1 1.4002(17) . ? C1 C2 1.514(2) . ? C1 C7 1.539(2) . ? C1 C6 1.5503(19) . ? C2 O2 1.2099(19) . ? C2 C3 1.530(2) . ? C3 C9 1.531(2) . ? C3 C8 1.536(2) . ? C3 C4 1.550(2) . ? C4 C5 1.539(2) . ? C4 C7 1.5450(19) . ? C4 H4 1.0000 . ? C5 C6 1.5483(19) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? O1 H1 0.82(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 O1 C1 C2 110.24(12) . . ? O1 C1 C7 120.40(12) . . ? C2 C1 C7 100.21(10) . . ? O1 C1 C6 116.84(11) . . ? C2 C1 C6 105.40(11) . . ? C7 C1 C6 101.60(11) . . ? O2 C2 C1 126.45(13) . . ? O2 C2 C3 126.10(13) . . ? C1 C2 C3 107.45(12) . . ? C2 C3 C9 110.69(12) . . ? C2 C3 C8 109.01(12) . . ? C9 C3 C8 108.88(12) . . ? C2 C3 C4 100.25(11) . . ? C9 C3 C4 115.92(12) . . ? C8 C3 C4 111.70(13) . . ? C5 C4 C7 100.11(11) . . ? C5 C4 C3 110.73(12) . . ? C7 C4 C3 102.58(11) . . ? C5 C4 H4 114.0 . . ? C7 C4 H4 114.0 . . ? C3 C4 H4 114.0 . . ? C4 C5 C6 102.75(11) . . ? C4 C5 H5A 111.2 . . ? C6 C5 H5A 111.2 . . ? C4 C5 H5B 111.2 . . ? C6 C5 H5B 111.2 . . ? H5A C5 H5B 109.1 . . ? C5 C6 C1 103.71(11) . . ? C5 C6 H6A 111.0 . . ? C1 C6 H6A 111.0 . . ? C5 C6 H6B 111.0 . . ? C1 C6 H6B 111.0 . . ? H6A C6 H6B 109.0 . . ? C1 C7 C4 94.29(11) . . ? C1 C7 H7A 112.9 . . ? C4 C7 H7A 112.9 . . ? C1 C7 H7B 112.9 . . ? C4 C7 H7B 112.9 . . ? H7A C7 H7B 110.3 . . ? C3 C8 H8A 109.5 . . ? C3 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C3 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C3 C9 H9A 109.5 . . ? C3 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C3 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C1 O1 H1 109.4(17) . . ? 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 O1 C1 C2 O2 -16.4(2) . . . . ? C7 C1 C2 O2 -144.31(15) . . . . ? C6 C1 C2 O2 110.52(16) . . . . ? O1 C1 C2 C3 162.66(12) . . . . ? C7 C1 C2 C3 34.75(13) . . . . ? C6 C1 C2 C3 -70.41(13) . . . . ? O2 C2 C3 C9 -57.9(2) . . . . ? C1 C2 C3 C9 123.00(13) . . . . ? O2 C2 C3 C8 61.80(19) . . . . ? C1 C2 C3 C8 -117.27(13) . . . . ? O2 C2 C3 C4 179.17(14) . . . . ? C1 C2 C3 C4 0.11(14) . . . . ? C2 C3 C4 C5 70.96(14) . . . . ? C9 C3 C4 C5 -48.19(17) . . . . ? C8 C3 C4 C5 -173.68(11) . . . . ? C2 C3 C4 C7 -35.11(14) . . . . ? C9 C3 C4 C7 -154.26(11) . . . . ? C8 C3 C4 C7 80.25(14) . . . . ? C7 C4 C5 C6 40.51(13) . . . . ? C3 C4 C5 C6 -67.18(14) . . . . ? C4 C5 C6 C1 -6.10(14) . . . . ? O1 C1 C6 C5 -163.67(12) . . . . ? C2 C1 C6 C5 73.53(13) . . . . ? C7 C1 C6 C5 -30.61(13) . . . . ? O1 C1 C7 C4 -174.78(12) . . . . ? C2 C1 C7 C4 -53.90(12) . . . . ? C6 C1 C7 C4 54.31(12) . . . . ? C5 C4 C7 C1 -58.36(12) . . . . ? C3 C4 C7 C1 55.73(12) . . . . ? 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 O2 0.82(3) 2.06(3) 2.7780(14) 145(2) 2_656 _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 30.02 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.264 _refine_diff_density_min -0.183 _refine_diff_density_rms 0.044 #============================================================================ data_3 _database_code_CSD 195490 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'Compound X' _chemical_melting_point ? _chemical_formula_moiety 'C10 H16 O' _chemical_formula_sum 'C10 H16 O' _chemical_formula_weight 152.23 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 orthorhombic _symmetry_space_group_name_H-M P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 5.9714(1) _cell_length_b 20.5466(5) _cell_length_c 22.5632(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2768.32(11) _cell_formula_units_Z 12 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2767 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 25.028 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.75 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.096 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1008 _exptl_absorpt_coefficient_mu 0.068 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 KappaCCD _diffrn_measurement_method 'CCD; rotation images; thick slices' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15934 _diffrn_reflns_av_R_equivalents 0.069 _diffrn_reflns_av_sigmaI/netI 0.0495 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 25.20 _reflns_number_total 2845 _reflns_number_gt 2300 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997' _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^)+(0.0360P)^2^+1.5000P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack ?) _refine_ls_number_reflns 2845 _refine_ls_number_parameters 304 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0671 _refine_ls_R_factor_gt 0.0508 _refine_ls_wR_factor_ref 0.1081 _refine_ls_wR_factor_gt 0.0996 _refine_ls_goodness_of_fit_ref 1.087 _refine_ls_restrained_S_all 1.087 _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 C1 C 0.3698(5) 0.71511(14) 0.32291(13) 0.0208(7) Uani 1 1 d . . . C2 C 0.3011(5) 0.65332(13) 0.35495(13) 0.0202(7) Uani 1 1 d . . . C3 C 0.4188(6) 0.65590(15) 0.41534(14) 0.0266(8) Uani 1 1 d . . . C4 C 0.5351(6) 0.72343(15) 0.41167(13) 0.0268(8) Uani 1 1 d . . . H4 H 0.6607 0.7294 0.4405 0.032 Uiso 1 1 calc R . . C5 C 0.3618(7) 0.77869(15) 0.41225(15) 0.0388(10) Uani 1 1 d . . . H5A H 0.4356 0.8216 0.4161 0.047 Uiso 1 1 calc R . . H5B H 0.2542 0.7732 0.4452 0.047 Uiso 1 1 calc R . . C6 C 0.2426(6) 0.77193(14) 0.35101(14) 0.0275(8) Uani 1 1 d . . . H6A H 0.0817 0.7616 0.3558 0.033 Uiso 1 1 calc R . . H6B H 0.2581 0.8121 0.3272 0.033 Uiso 1 1 calc R . . C7 C 0.6072(5) 0.72586(15) 0.34656(13) 0.0239(7) Uani 1 1 d . . . H7A H 0.6705 0.7685 0.3350 0.029 Uiso 1 1 calc R . . H7B H 0.7114 0.6903 0.3357 0.029 Uiso 1 1 calc R . . C8 C 0.1681(6) 0.60747(14) 0.33440(16) 0.0302(8) Uani 1 1 d . . . H8A H 0.1050 0.6114 0.2959 0.036 Uiso 1 1 calc R . . H8B H 0.1352 0.5704 0.3581 0.036 Uiso 1 1 calc R . . C9 C 0.5930(7) 0.60132(16) 0.42039(16) 0.0364(9) Uani 1 1 d . . . H9A H 0.7011 0.6051 0.3879 0.055 Uiso 1 1 calc R . . H9B H 0.5177 0.5590 0.4181 0.055 Uiso 1 1 calc R . . H9C H 0.6715 0.6050 0.4584 0.055 Uiso 1 1 calc R . . C10 C 0.2531(8) 0.64932(18) 0.46721(15) 0.0446(11) Uani 1 1 d . . . H10A H 0.1978 0.6045 0.4691 0.067 Uiso 1 1 calc R . . H10B H 0.1268 0.6791 0.4611 0.067 Uiso 1 1 calc R . . H10C H 0.3291 0.6602 0.5044 0.067 Uiso 1 1 calc R . . C11 C -0.3176(5) 0.56863(13) 0.19393(13) 0.0199(7) Uani 1 1 d . . . C12 C -0.4005(5) 0.56966(13) 0.13005(13) 0.0209(7) Uani 1 1 d . . . C13 C -0.2978(6) 0.51039(13) 0.09963(13) 0.0222(7) Uani 1 1 d . . . C14 C -0.1796(6) 0.47702(13) 0.15309(13) 0.0223(7) Uani 1 1 d . . . H14 H -0.0629 0.4445 0.1416 0.027 Uiso 1 1 calc R . . C15 C -0.3525(6) 0.45149(14) 0.19812(14) 0.0267(8) Uani 1 1 d . . . H15A H -0.2803 0.4236 0.2283 0.032 Uiso 1 1 calc R . . H15B H -0.4720 0.4264 0.1781 0.032 Uiso 1 1 calc R . . C16 C -0.4481(6) 0.51482(13) 0.22657(14) 0.0238(7) Uani 1 1 d . . . H16A H -0.6112 0.5188 0.2196 0.029 Uiso 1 1 calc R . . H16B H -0.4189 0.5161 0.2697 0.029 Uiso 1 1 calc R . . C17 C -0.0877(6) 0.53642(15) 0.18734(14) 0.0231(7) Uani 1 1 d . . . H17A H -0.0197 0.5245 0.2259 0.028 Uiso 1 1 calc R . . H17B H 0.0183 0.5628 0.1636 0.028 Uiso 1 1 calc R . . C18 C -0.5392(6) 0.61297(14) 0.10753(15) 0.0276(8) Uani 1 1 d . . . H18A H -0.5957 0.6471 0.1317 0.033 Uiso 1 1 calc R . . H18B H -0.5826 0.6101 0.0671 0.033 Uiso 1 1 calc R . . C19 C -0.1234(7) 0.53142(15) 0.05322(14) 0.0318(9) Uani 1 1 d . . . H19A H -0.1986 0.5545 0.0208 0.048 Uiso 1 1 calc R . . H19B H -0.0474 0.4928 0.0375 0.048 Uiso 1 1 calc R . . H19C H -0.0132 0.5603 0.0718 0.048 Uiso 1 1 calc R . . C20 C -0.4737(7) 0.46845(15) 0.06875(15) 0.0332(9) Uani 1 1 d . . . H20A H -0.5350 0.4922 0.0347 0.050 Uiso 1 1 calc R . . H20B H -0.5946 0.4583 0.0966 0.050 Uiso 1 1 calc R . . H20C H -0.4045 0.4279 0.0551 0.050 Uiso 1 1 calc R . . C21 C -0.0239(5) 0.76756(13) 0.14335(13) 0.0204(7) Uani 1 1 d . . . C22 C -0.1091(6) 0.83318(14) 0.16388(13) 0.0224(7) Uani 1 1 d . . . C23 C -0.0358(5) 0.88246(13) 0.11624(13) 0.0197(7) Uani 1 1 d . . . C24 C 0.0867(6) 0.83663(14) 0.07169(13) 0.0216(7) Uani 1 1 d . . . H24 H 0.1940 0.8594 0.0447 0.026 Uiso 1 1 calc R . . C25 C -0.0820(6) 0.79236(14) 0.03957(13) 0.0247(7) Uani 1 1 d . . . H25A H -0.0088 0.7678 0.0072 0.030 Uiso 1 1 calc R . . H25B H -0.2076 0.8180 0.0230 0.030 Uiso 1 1 calc R . . C26 C -0.1645(6) 0.74592(14) 0.08936(13) 0.0237(7) Uani 1 1 d . . . H26A H -0.3267 0.7516 0.0969 0.028 Uiso 1 1 calc R . . H26B H -0.1349 0.6999 0.0791 0.028 Uiso 1 1 calc R . . C27 C 0.1972(5) 0.78692(14) 0.11353(13) 0.0224(7) Uani 1 1 d . . . H27A H 0.2688 0.7504 0.0921 0.027 Uiso 1 1 calc R . . H27B H 0.3048 0.8071 0.1414 0.027 Uiso 1 1 calc R . . C28 C -0.2257(7) 0.84489(18) 0.21219(15) 0.0433(10) Uani 1 1 d . . . H28A H -0.2641 0.8102 0.2381 0.052 Uiso 1 1 calc R . . H28B H -0.2715 0.8881 0.2212 0.052 Uiso 1 1 calc R . . C29 C 0.1268(6) 0.93261(14) 0.14153(15) 0.0314(8) Uani 1 1 d . . . H29A H 0.2584 0.9103 0.1577 0.047 Uiso 1 1 calc R . . H29B H 0.0527 0.9572 0.1731 0.047 Uiso 1 1 calc R . . H29C H 0.1737 0.9625 0.1100 0.047 Uiso 1 1 calc R . . C30 C -0.2361(6) 0.91917(15) 0.08987(15) 0.0319(8) Uani 1 1 d . . . H30A H -0.2964 0.9494 0.1195 0.048 Uiso 1 1 calc R . . H30B H -0.3524 0.8880 0.0784 0.048 Uiso 1 1 calc R . . H30C H -0.1874 0.9436 0.0549 0.048 Uiso 1 1 calc R . . O1 O 0.3413(4) 0.71365(10) 0.26024(8) 0.0265(5) Uani 1 1 d . . . H1 H 0.4204 0.6838 0.2457 0.040 Uiso 1 1 d R . . O2 O -0.3299(4) 0.62872(9) 0.22440(9) 0.0230(5) Uani 1 1 d . . . H2A H -0.2394 0.6552 0.2092 0.035 Uiso 1 1 d R . . O3 O -0.0200(4) 0.71762(9) 0.18669(9) 0.0268(5) Uani 1 1 d . . . H3 H 0.0937 0.7221 0.2083 0.040 Uiso 1 1 d 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 C1 0.0264(18) 0.0191(15) 0.0170(16) 0.0001(13) -0.0022(14) 0.0020(15) C2 0.0205(17) 0.0153(14) 0.0249(17) -0.0032(13) 0.0054(15) 0.0042(14) C3 0.034(2) 0.0258(16) 0.0201(17) 0.0027(14) 0.0026(16) -0.0018(16) C4 0.034(2) 0.0303(17) 0.0162(16) -0.0022(14) -0.0036(16) -0.0050(16) C5 0.061(3) 0.0265(17) 0.0293(19) -0.0064(15) 0.003(2) -0.0076(19) C6 0.031(2) 0.0211(15) 0.0301(18) -0.0015(14) 0.0017(16) 0.0011(15) C7 0.0256(18) 0.0248(16) 0.0214(17) 0.0045(13) 0.0001(15) -0.0062(15) C8 0.034(2) 0.0224(16) 0.0344(19) -0.0027(14) 0.0029(18) -0.0024(17) C9 0.039(2) 0.0334(18) 0.037(2) 0.0115(16) -0.0053(19) 0.0004(18) C10 0.058(3) 0.051(2) 0.0244(19) 0.0039(17) 0.010(2) -0.009(2) C11 0.0182(17) 0.0177(15) 0.0238(17) 0.0005(13) -0.0026(15) -0.0023(14) C12 0.0243(18) 0.0169(14) 0.0216(17) 0.0027(13) -0.0003(15) -0.0041(14) C13 0.030(2) 0.0181(14) 0.0188(16) 0.0001(13) -0.0036(15) -0.0007(15) C14 0.0274(18) 0.0193(15) 0.0202(17) -0.0020(12) -0.0014(15) 0.0052(14) C15 0.033(2) 0.0226(16) 0.0247(18) 0.0028(13) -0.0028(16) -0.0017(16) C16 0.0262(19) 0.0235(15) 0.0217(16) 0.0029(13) 0.0024(15) -0.0009(15) C17 0.0225(18) 0.0264(16) 0.0205(16) 0.0012(13) -0.0010(15) 0.0013(15) C18 0.034(2) 0.0219(16) 0.0272(18) 0.0035(13) -0.0060(16) -0.0021(16) C19 0.045(2) 0.0303(17) 0.0197(17) -0.0008(14) 0.0026(17) 0.0021(18) C20 0.046(2) 0.0252(17) 0.0281(19) -0.0018(14) -0.0124(18) -0.0023(18) C21 0.0216(17) 0.0185(15) 0.0211(16) 0.0050(12) -0.0012(15) -0.0002(14) C22 0.0244(18) 0.0244(15) 0.0183(16) 0.0004(13) -0.0029(15) -0.0002(15) C23 0.0228(18) 0.0169(14) 0.0195(16) 0.0000(13) 0.0016(15) -0.0020(14) C24 0.0212(17) 0.0255(15) 0.0181(16) 0.0005(13) 0.0020(14) -0.0011(15) C25 0.0291(19) 0.0273(16) 0.0178(16) -0.0023(13) 0.0018(15) 0.0006(16) C26 0.0228(17) 0.0218(15) 0.0265(17) 0.0006(13) -0.0060(16) -0.0025(15) C27 0.0213(17) 0.0198(14) 0.0261(17) -0.0018(14) 0.0004(15) 0.0034(15) C28 0.060(3) 0.038(2) 0.032(2) 0.0045(16) 0.022(2) 0.010(2) C29 0.040(2) 0.0218(16) 0.0324(19) -0.0024(14) -0.0023(18) -0.0029(16) C30 0.036(2) 0.0286(17) 0.0308(19) 0.0052(15) 0.0021(18) 0.0071(17) O1 0.0315(13) 0.0323(12) 0.0158(11) -0.0013(9) -0.0047(11) 0.0050(11) O2 0.0257(12) 0.0196(10) 0.0239(11) -0.0032(9) 0.0037(11) -0.0040(10) O3 0.0278(13) 0.0243(11) 0.0284(12) 0.0123(9) -0.0100(11) -0.0058(11) _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 O1 1.424(3) . ? C1 C2 1.517(4) . ? C1 C7 1.531(4) . ? C1 C6 1.530(4) . ? C2 C8 1.317(4) . ? C2 C3 1.534(4) . ? C3 C9 1.534(5) . ? C3 C10 1.539(5) . ? C3 C4 1.554(4) . ? C4 C7 1.532(4) . ? C4 C5 1.537(5) . ? C5 C6 1.561(5) . ? C11 O2 1.415(3) . ? C11 C12 1.524(4) . ? C11 C17 1.531(4) . ? C11 C16 1.540(4) . ? C12 C18 1.318(4) . ? C12 C13 1.526(4) . ? C13 C20 1.527(5) . ? C13 C19 1.539(5) . ? C13 C14 1.557(4) . ? C14 C15 1.541(4) . ? C14 C17 1.545(4) . ? C15 C16 1.559(4) . ? C21 O3 1.418(3) . ? C21 C22 1.514(4) . ? C21 C27 1.534(4) . ? C21 C26 1.545(4) . ? C22 C28 1.315(5) . ? C22 C23 1.540(4) . ? C23 C29 1.526(4) . ? C23 C30 1.534(5) . ? C23 C24 1.559(4) . ? C24 C27 1.539(4) . ? C24 C25 1.539(4) . ? C25 C26 1.554(4) . ? O1 O3 2.723(3) . ? O1 O2 2.749(3) 1_655 ? O2 O3 2.736(3) . ? O2 O1 2.749(3) 1_455 ? 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 O1 C1 C2 115.0(2) . . ? O1 C1 C7 117.4(3) . . ? C2 C1 C7 101.8(3) . . ? O1 C1 C6 111.6(2) . . ? C2 C1 C6 107.9(2) . . ? C7 C1 C6 101.8(2) . . ? C8 C2 C1 126.4(3) . . ? C8 C2 C3 127.9(3) . . ? C1 C2 C3 105.7(2) . . ? C9 C3 C2 110.6(3) . . ? C9 C3 C10 108.4(3) . . ? C2 C3 C10 112.2(3) . . ? C9 C3 C4 110.7(3) . . ? C2 C3 C4 100.9(2) . . ? C10 C3 C4 114.0(3) . . ? C7 C4 C5 100.0(3) . . ? C7 C4 C3 101.9(2) . . ? C5 C4 C3 111.0(3) . . ? C4 C5 C6 103.5(3) . . ? C1 C6 C5 102.0(3) . . ? C1 C7 C4 94.0(2) . . ? O2 C11 C12 115.5(2) . . ? O2 C11 C17 118.1(2) . . ? C12 C11 C17 101.8(2) . . ? O2 C11 C16 111.6(2) . . ? C12 C11 C16 107.3(2) . . ? C17 C11 C16 100.9(2) . . ? C18 C12 C11 125.3(3) . . ? C18 C12 C13 128.2(3) . . ? C11 C12 C13 106.5(2) . . ? C12 C13 C20 112.3(3) . . ? C12 C13 C19 110.7(2) . . ? C20 C13 C19 108.3(3) . . ? C12 C13 C14 100.7(2) . . ? C20 C13 C14 114.6(2) . . ? C19 C13 C14 110.1(3) . . ? C15 C14 C17 100.2(2) . . ? C15 C14 C13 110.9(3) . . ? C17 C14 C13 101.6(2) . . ? C14 C15 C16 103.5(2) . . ? C11 C16 C15 102.5(2) . . ? C11 C17 C14 94.1(2) . . ? O3 C21 C22 116.0(2) . . ? O3 C21 C27 118.4(3) . . ? C22 C21 C27 101.1(2) . . ? O3 C21 C26 110.2(2) . . ? C22 C21 C26 108.4(3) . . ? C27 C21 C26 101.3(2) . . ? C28 C22 C21 126.5(3) . . ? C28 C22 C23 127.5(3) . . ? C21 C22 C23 106.0(2) . . ? C29 C23 C30 108.0(2) . . ? C29 C23 C22 111.3(3) . . ? C30 C23 C22 111.8(3) . . ? C29 C23 C24 110.5(3) . . ? C30 C23 C24 114.4(3) . . ? C22 C23 C24 100.7(2) . . ? C27 C24 C25 100.2(2) . . ? C27 C24 C23 101.9(2) . . ? C25 C24 C23 110.7(3) . . ? C24 C25 C26 103.3(2) . . ? C21 C26 C25 102.8(2) . . ? C21 C27 C24 94.1(2) . . ? C1 O1 O3 134.33(19) . . ? C1 O1 O2 102.73(17) . 1_655 ? O3 O1 O2 113.94(9) . 1_655 ? C11 O2 O3 113.36(17) . . ? C11 O2 O1 137.21(19) . 1_455 ? O3 O2 O1 98.68(9) . 1_455 ? C21 O3 O1 117.08(18) . . ? C21 O3 O2 133.36(19) . . ? O1 O3 O2 109.05(9) . . ? 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 O1 C1 C2 C8 -19.3(5) . . . . ? C7 C1 C2 C8 -147.4(3) . . . . ? C6 C1 C2 C8 105.9(4) . . . . ? O1 C1 C2 C3 160.6(3) . . . . ? C7 C1 C2 C3 32.5(3) . . . . ? C6 C1 C2 C3 -74.2(3) . . . . ? C8 C2 C3 C9 65.7(4) . . . . ? C1 C2 C3 C9 -114.2(3) . . . . ? C8 C2 C3 C10 -55.4(4) . . . . ? C1 C2 C3 C10 124.7(3) . . . . ? C8 C2 C3 C4 -177.1(3) . . . . ? C1 C2 C3 C4 3.0(3) . . . . ? C9 C3 C4 C7 79.4(3) . . . . ? C2 C3 C4 C7 -37.6(3) . . . . ? C10 C3 C4 C7 -158.1(3) . . . . ? C9 C3 C4 C5 -174.9(3) . . . . ? C2 C3 C4 C5 68.0(3) . . . . ? C10 C3 C4 C5 -52.4(4) . . . . ? C7 C4 C5 C6 37.6(3) . . . . ? C3 C4 C5 C6 -69.3(3) . . . . ? O1 C1 C6 C5 -160.7(3) . . . . ? C2 C1 C6 C5 72.0(3) . . . . ? C7 C1 C6 C5 -34.7(3) . . . . ? C4 C5 C6 C1 -1.9(3) . . . . ? O1 C1 C7 C4 179.5(2) . . . . ? C2 C1 C7 C4 -54.0(3) . . . . ? C6 C1 C7 C4 57.4(3) . . . . ? C5 C4 C7 C1 -57.6(3) . . . . ? C3 C4 C7 C1 56.5(3) . . . . ? O2 C11 C12 C18 -21.9(5) . . . . ? C17 C11 C12 C18 -151.1(3) . . . . ? C16 C11 C12 C18 103.3(3) . . . . ? O2 C11 C12 C13 160.0(3) . . . . ? C17 C11 C12 C13 30.7(3) . . . . ? C16 C11 C12 C13 -74.9(3) . . . . ? C18 C12 C13 C20 -50.6(4) . . . . ? C11 C12 C13 C20 127.4(3) . . . . ? C18 C12 C13 C19 70.5(4) . . . . ? C11 C12 C13 C19 -111.4(3) . . . . ? C18 C12 C13 C14 -173.0(3) . . . . ? C11 C12 C13 C14 5.1(3) . . . . ? C12 C13 C14 C15 66.9(3) . . . . ? C20 C13 C14 C15 -53.8(3) . . . . ? C19 C13 C14 C15 -176.2(2) . . . . ? C12 C13 C14 C17 -38.9(3) . . . . ? C20 C13 C14 C17 -159.6(3) . . . . ? C19 C13 C14 C17 78.0(3) . . . . ? C17 C14 C15 C16 35.8(3) . . . . ? C13 C14 C15 C16 -70.9(3) . . . . ? O2 C11 C16 C15 -162.8(3) . . . . ? C12 C11 C16 C15 69.7(3) . . . . ? C17 C11 C16 C15 -36.5(3) . . . . ? C14 C15 C16 C11 0.1(3) . . . . ? O2 C11 C17 C14 179.7(2) . . . . ? C12 C11 C17 C14 -52.7(2) . . . . ? C16 C11 C17 C14 57.9(3) . . . . ? C15 C14 C17 C11 -57.3(3) . . . . ? C13 C14 C17 C11 56.7(3) . . . . ? O3 C21 C22 C28 -16.9(5) . . . . ? C27 C21 C22 C28 -146.3(4) . . . . ? C26 C21 C22 C28 107.6(4) . . . . ? O3 C21 C22 C23 164.3(3) . . . . ? C27 C21 C22 C23 34.8(3) . . . . ? C26 C21 C22 C23 -71.2(3) . . . . ? C28 C22 C23 C29 64.5(5) . . . . ? C21 C22 C23 C29 -116.6(3) . . . . ? C28 C22 C23 C30 -56.4(5) . . . . ? C21 C22 C23 C30 122.4(3) . . . . ? C28 C22 C23 C24 -178.3(4) . . . . ? C21 C22 C23 C24 0.5(3) . . . . ? C29 C23 C24 C27 82.1(3) . . . . ? C30 C23 C24 C27 -155.8(3) . . . . ? C22 C23 C24 C27 -35.7(3) . . . . ? C29 C23 C24 C25 -172.0(2) . . . . ? C30 C23 C24 C25 -49.9(3) . . . . ? C22 C23 C24 C25 70.2(3) . . . . ? C27 C24 C25 C26 37.9(3) . . . . ? C23 C24 C25 C26 -69.1(3) . . . . ? O3 C21 C26 C25 -160.2(2) . . . . ? C22 C21 C26 C25 71.8(3) . . . . ? C27 C21 C26 C25 -34.0(3) . . . . ? C24 C25 C26 C21 -2.5(3) . . . . ? O3 C21 C27 C24 177.0(2) . . . . ? C22 C21 C27 C24 -55.0(3) . . . . ? C26 C21 C27 C24 56.5(3) . . . . ? C25 C24 C27 C21 -57.8(3) . . . . ? C23 C24 C27 C21 56.1(3) . . . . ? C2 C1 O1 O3 72.6(3) . . . . ? C7 C1 O1 O3 -167.69(19) . . . . ? C6 C1 O1 O3 -50.7(4) . . . . ? C2 C1 O1 O2 -70.8(3) . . . 1_655 ? C7 C1 O1 O2 49.0(3) . . . 1_655 ? C6 C1 O1 O2 165.9(2) . . . 1_655 ? C12 C11 O2 O3 -72.1(3) . . . . ? C17 C11 O2 O3 48.7(3) . . . . ? C16 C11 O2 O3 164.9(2) . . . . ? C12 C11 O2 O1 63.0(3) . . . 1_455 ? C17 C11 O2 O1 -176.20(19) . . . 1_455 ? C16 C11 O2 O1 -59.9(3) . . . 1_455 ? C22 C21 O3 O1 -83.3(3) . . . . ? C27 C21 O3 O1 37.2(3) . . . . ? C26 C21 O3 O1 153.1(2) . . . . ? C22 C21 O3 O2 87.4(3) . . . . ? C27 C21 O3 O2 -152.0(2) . . . . ? C26 C21 O3 O2 -36.1(4) . . . . ? C1 O1 O3 C21 123.7(3) . . . . ? O2 O1 O3 C21 -95.9(2) 1_655 . . . ? C1 O1 O3 O2 -49.2(3) . . . . ? O2 O1 O3 O2 91.22(11) 1_655 . . . ? C11 O2 O3 C21 92.1(3) . . . . ? O1 O2 O3 C21 -58.8(3) 1_455 . . . ? C11 O2 O3 O1 -96.59(19) . . . . ? O1 O2 O3 O1 112.43(10) 1_455 . . . ? 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 O2 0.84 1.93 2.749(3) 163.3 1_655 O2 H2A O3 0.84 1.90 2.736(3) 171.4 . O3 H3 O1 0.84 1.90 2.723(3) 168.2 . _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 25.20 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.21 _refine_diff_density_min -0.21 _refine_diff_density_rms 0.042 #=========================================================================== data_4 _database_code_CSD 195491 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'Compound X' _chemical_melting_point ? _chemical_formula_moiety 'C10 H16 O1' _chemical_formula_sum 'C10 H16 O1' _chemical_formula_weight 152.23 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 tetragonal _symmetry_space_group_name_H-M 'P 41 21 2' _symmetry_space_group_name_Hall 'P 4abw 2nw' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z+3/4' '-x, -y, z+1/2' '-x+1/2, y+1/2, -z+1/4' 'y, x, -z' 'y+1/2, -x+1/2, z+3/4' '-y+1/2, x+1/2, z+1/4' '-y, -x, -z+1/2' _cell_length_a 10.7633(1) _cell_length_b 10.7633(1) _cell_length_c 31.3398(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3630.67(8) _cell_formula_units_Z 16 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6411 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 33.142 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.114 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1344 _exptl_absorpt_coefficient_mu 0.069 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22563 _diffrn_reflns_av_R_equivalents 0.0324 _diffrn_reflns_av_sigmaI/netI 0.0324 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -48 _diffrn_reflns_limit_l_max 44 _diffrn_reflns_theta_min 2.00 _diffrn_reflns_theta_max 33.14 _reflns_number_total 4009 _reflns_number_gt 3345 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0730P)^2^+0.4412P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 4009 _refine_ls_number_parameters 234 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0606 _refine_ls_R_factor_gt 0.0482 _refine_ls_wR_factor_ref 0.1320 _refine_ls_wR_factor_gt 0.1244 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _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 0.96147(12) 0.21510(10) 0.01064(4) 0.0300(2) Uani 1 1 d . . . H1 H 0.979(3) 0.185(2) -0.0097(7) 0.053(7) Uiso 1 1 d . . . C1 C 0.8262(2) 0.3979(3) 0.00556(10) 0.0219(4) Uani 0.832(3) 1 d P A 1 C2 C 0.95619(15) 0.34389(14) 0.00157(6) 0.0203(3) Uani 0.832(3) 1 d P A 1 C3 C 1.00838(18) 0.38453(18) -0.04223(6) 0.0263(3) Uani 0.832(3) 1 d P A 1 H3A H 0.9487 0.3667 -0.0655 0.032 Uiso 0.832(3) 1 calc PR A 1 H3B H 1.0882 0.3426 -0.0485 0.032 Uiso 0.832(3) 1 calc PR A 1 C4 C 1.0267(2) 0.52647(16) -0.03620(6) 0.0326(4) Uani 0.832(3) 1 d P A 1 H4A H 0.9749 0.5742 -0.0565 0.039 Uiso 0.832(3) 1 calc PR A 1 H4B H 1.1149 0.5502 -0.0401 0.039 Uiso 0.832(3) 1 calc PR A 1 C5 C 0.98325(17) 0.54881(14) 0.01140(6) 0.0344(3) Uani 1 1 d . . . H5 H 1.0145 0.6274 0.0246 0.041 Uiso 1 1 calc R A 1 C6 C 0.84087(16) 0.53518(14) 0.01096(6) 0.0324(3) Uani 1 1 d . A . H6A H 0.8036 0.5642 0.0381 0.039 Uiso 1 1 calc R B 1 H6B H 0.8033 0.5813 -0.0131 0.039 Uiso 1 1 calc R B 1 C7 C 1.02905(16) 0.42852(16) 0.03325(5) 0.0251(3) Uani 0.832(3) 1 d P A 1 C8 C 1.16983(18) 0.4075(2) 0.03280(7) 0.0372(5) Uani 0.832(3) 1 d P A 1 H8A H 1.2096 0.4646 0.0530 0.056 Uiso 0.832(3) 1 calc PR A 1 H8B H 1.2020 0.4227 0.0040 0.056 Uiso 0.832(3) 1 calc PR A 1 H8C H 1.1879 0.3216 0.0411 0.056 Uiso 0.832(3) 1 calc PR A 1 C9 C 0.9843(2) 0.4156(2) 0.07952(6) 0.0337(4) Uani 0.832(3) 1 d P A 1 H9A H 1.0121 0.3357 0.0911 0.051 Uiso 0.832(3) 1 calc PR A 1 H9B H 0.8934 0.4196 0.0803 0.051 Uiso 0.832(3) 1 calc PR A 1 H9C H 1.0189 0.4833 0.0967 0.051 Uiso 0.832(3) 1 calc PR A 1 C10 C 0.71991(15) 0.33145(17) 0.00258(5) 0.0319(3) Uani 1 1 d . . . H10A H 0.6418 0.3724 0.0039 0.038 Uiso 1 1 calc R A 1 H10B H 0.7233 0.2438 -0.0008 0.038 Uiso 1 1 calc R A 1 O2 O 1.07743(11) 0.03819(12) 0.05669(3) 0.0324(3) Uani 1 1 d . . . H2 H 1.037(2) 0.097(2) 0.0507(6) 0.038(6) Uiso 1 1 d . . . C11 C 1.07033(14) 0.05337(15) 0.13515(4) 0.0281(3) Uani 1 1 d . . . C12 C 1.03769(13) -0.01843(13) 0.09492(4) 0.0248(3) Uani 1 1 d . . . C13 C 1.09703(17) -0.14713(16) 0.10056(6) 0.0369(4) Uani 1 1 d . . . H13A H 1.1844 -0.1402 0.1101 0.044 Uiso 1 1 calc R . . H13B H 1.0941 -0.1954 0.0737 0.044 Uiso 1 1 calc R . . C14 C 1.01436(19) -0.20736(18) 0.13546(7) 0.0448(4) Uani 1 1 d . . . H14A H 0.9733 -0.2834 0.1247 0.054 Uiso 1 1 calc R . . H14B H 1.0637 -0.2285 0.1611 0.054 Uiso 1 1 calc R . . C15 C 0.91886(15) -0.10554(16) 0.14533(5) 0.0326(3) Uani 1 1 d . . . H15 H 0.8417 -0.1357 0.1598 0.039 Uiso 1 1 calc R . . C16 C 0.99069(16) -0.00347(19) 0.17017(5) 0.0363(4) Uani 1 1 d . . . H16A H 0.9334 0.0586 0.1827 0.044 Uiso 1 1 calc R . . H16B H 1.0425 -0.0398 0.1931 0.044 Uiso 1 1 calc R . . C17 C 0.89706(14) -0.04348(15) 0.10141(4) 0.0283(3) Uani 1 1 d . . . C18 C 0.8409(2) -0.1298(2) 0.06788(6) 0.0458(4) Uani 1 1 d . . . H18A H 0.7542 -0.1475 0.0752 0.069 Uiso 1 1 calc R . . H18B H 0.8881 -0.2076 0.0670 0.069 Uiso 1 1 calc R . . H18C H 0.8443 -0.0896 0.0398 0.069 Uiso 1 1 calc R . . C19 C 0.81948(15) 0.07593(17) 0.10331(5) 0.0339(3) Uani 1 1 d . . . H19A H 0.8141 0.1125 0.0747 0.051 Uiso 1 1 calc R . . H19B H 0.8590 0.1352 0.1228 0.051 Uiso 1 1 calc R . . H19C H 0.7358 0.0564 0.1136 0.051 Uiso 1 1 calc R . . C20 C 1.15232(17) 0.14519(18) 0.13810(5) 0.0393(4) Uani 1 1 d . . . H20A H 1.1968 0.1714 0.1135 0.047 Uiso 1 1 calc R . . H20B H 1.1664 0.1846 0.1648 0.047 Uiso 1 1 calc R . . C1A C 0.805(2) 0.383(2) 0.0051(8) 0.0352(11) Uiso 0.168(3) 1 d P A 2 C2A C 0.9405(11) 0.3451(11) 0.0209(4) 0.0352(11) Uiso 0.168(3) 1 d P A 2 C3A C 0.9644(11) 0.3779(11) 0.0682(4) 0.0352(11) Uiso 0.168(3) 1 d P A 2 H3A1 H 1.0381 0.3334 0.0794 0.042 Uiso 0.168(3) 1 calc PR A 2 H3A2 H 0.8914 0.3575 0.0862 0.042 Uiso 0.168(3) 1 calc PR A 2 C4A C 0.9873(10) 0.5208(9) 0.0667(3) 0.0352(11) Uiso 0.168(3) 1 d P A 2 H4A1 H 1.0689 0.5430 0.0791 0.042 Uiso 0.168(3) 1 calc PR A 2 H4A2 H 0.9210 0.5670 0.0818 0.042 Uiso 0.168(3) 1 calc PR A 2 C7A C 1.0274(10) 0.4332(10) -0.0042(3) 0.0352(11) Uiso 0.168(3) 1 d P A 2 C8A C 1.0056(11) 0.4331(12) -0.0512(4) 0.0352(11) Uiso 0.168(3) 1 d P A 2 H8A1 H 0.9388 0.3746 -0.0581 0.053 Uiso 0.168(3) 1 calc PR A 2 H8A2 H 1.0819 0.4079 -0.0660 0.053 Uiso 0.168(3) 1 calc PR A 2 H8A3 H 0.9818 0.5167 -0.0605 0.053 Uiso 0.168(3) 1 calc PR A 2 C9A C 1.1673(10) 0.4114(11) 0.0074(4) 0.0352(11) Uiso 0.168(3) 1 d P A 2 H9A1 H 1.2198 0.4633 -0.0109 0.053 Uiso 0.168(3) 1 calc PR A 2 H9A2 H 1.1883 0.3237 0.0029 0.053 Uiso 0.168(3) 1 calc PR A 2 H9A3 H 1.1814 0.4334 0.0373 0.053 Uiso 0.168(3) 1 calc PR A 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 0.0461(7) 0.0161(4) 0.0279(5) -0.0003(4) 0.0045(5) 0.0012(4) C1 0.0227(11) 0.0205(10) 0.0226(7) -0.0001(7) -0.0010(8) -0.0035(7) C2 0.0257(7) 0.0139(6) 0.0213(6) -0.0013(5) 0.0034(6) -0.0007(5) C3 0.0339(9) 0.0206(7) 0.0244(7) -0.0007(6) 0.0087(6) -0.0016(7) C4 0.0406(10) 0.0196(7) 0.0374(9) 0.0017(7) 0.0103(8) -0.0036(7) C5 0.0377(8) 0.0180(6) 0.0476(9) -0.0055(6) 0.0046(7) -0.0038(6) C6 0.0340(7) 0.0228(6) 0.0405(8) -0.0007(6) 0.0077(6) 0.0046(6) C7 0.0236(7) 0.0239(7) 0.0278(7) -0.0068(6) 0.0018(6) -0.0031(6) C8 0.0250(8) 0.0445(11) 0.0421(11) -0.0067(9) -0.0012(8) -0.0018(8) C9 0.0364(10) 0.0389(10) 0.0257(8) -0.0094(7) -0.0004(7) -0.0036(8) C10 0.0299(7) 0.0411(8) 0.0246(6) -0.0011(6) -0.0002(6) -0.0056(6) O2 0.0362(6) 0.0408(6) 0.0204(4) 0.0083(4) 0.0067(4) 0.0088(5) C11 0.0253(6) 0.0381(8) 0.0208(5) 0.0043(5) 0.0012(5) -0.0033(5) C12 0.0277(6) 0.0269(6) 0.0199(5) 0.0038(5) 0.0034(5) 0.0030(5) C13 0.0363(8) 0.0331(8) 0.0413(8) 0.0087(7) 0.0037(7) 0.0100(6) C14 0.0402(9) 0.0360(9) 0.0582(11) 0.0202(8) 0.0018(9) 0.0014(7) C15 0.0291(7) 0.0373(8) 0.0314(6) 0.0099(6) 0.0012(6) -0.0059(6) C16 0.0330(7) 0.0547(10) 0.0213(5) 0.0055(6) 0.0022(5) -0.0107(7) C17 0.0268(6) 0.0315(7) 0.0265(6) -0.0006(5) -0.0020(5) -0.0008(5) C18 0.0483(10) 0.0443(10) 0.0447(9) -0.0112(8) -0.0115(8) -0.0026(8) C19 0.0264(7) 0.0382(8) 0.0370(7) 0.0017(7) 0.0023(6) 0.0045(6) C20 0.0388(9) 0.0488(10) 0.0302(7) 0.0010(7) 0.0002(7) -0.0147(8) _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 C2 1.4162(18) . ? O1 C2A 1.453(12) . ? C1 C10 1.353(2) . ? C1 C6 1.496(3) . ? C1 C2 1.520(3) . ? C2 C3 1.546(2) . ? C2 C7 1.559(2) . ? C3 C4 1.552(3) . ? C4 C5 1.582(3) . ? C5 C7A 1.418(11) . ? C5 C6 1.540(2) . ? C5 C7 1.545(2) . ? C5 C4A 1.759(10) . ? C6 C1A 1.69(2) . ? C7 C8 1.532(3) . ? C7 C9 1.534(3) . ? C10 C1A 1.079(19) . ? O2 C12 1.4105(16) . ? C11 C20 1.328(2) . ? C11 C12 1.520(2) . ? C11 C16 1.521(2) . ? C12 C13 1.536(2) . ? C12 C17 1.551(2) . ? C13 C14 1.552(3) . ? C14 C15 1.534(3) . ? C15 C17 1.548(2) . ? C15 C16 1.553(2) . ? C17 C18 1.527(2) . ? C17 C19 1.534(2) . ? C1A C2A 1.59(3) . ? C2A C7A 1.547(16) . ? C2A C3A 1.546(17) . ? C3A C4A 1.558(15) . ? C7A C8A 1.494(15) . ? C7A C9A 1.567(15) . ? 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 O1 C2A 25.3(5) . . ? C10 C1 C6 128.3(2) . . ? C10 C1 C2 124.8(2) . . ? C6 C1 C2 106.88(14) . . ? O1 C2 C1 113.25(15) . . ? O1 C2 C3 116.15(14) . . ? C1 C2 C3 107.41(17) . . ? O1 C2 C7 115.07(14) . . ? C1 C2 C7 100.77(14) . . ? C3 C2 C7 102.55(13) . . ? C2 C3 C4 102.51(13) . . ? C3 C4 C5 103.11(13) . . ? C7A C5 C6 104.3(4) . . ? C7A C5 C7 46.4(4) . . ? C6 C5 C7 103.98(13) . . ? C7A C5 C4 56.2(4) . . ? C6 C5 C4 105.77(15) . . ? C7 C5 C4 101.31(13) . . ? C7A C5 C4A 100.4(5) . . ? C6 C5 C4A 91.0(4) . . ? C7 C5 C4A 54.0(3) . . ? C4 C5 C4A 153.6(4) . . ? C1 C6 C5 101.53(15) . . ? C1 C6 C1A 7.0(8) . . ? C5 C6 C1A 108.5(8) . . ? C8 C7 C9 107.80(16) . . ? C8 C7 C5 115.81(16) . . ? C9 C7 C5 113.23(15) . . ? C8 C7 C2 113.91(15) . . ? C9 C7 C2 113.02(15) . . ? C5 C7 C2 92.68(12) . . ? C1A C10 C1 0.9(15) . . ? C20 C11 C12 126.12(13) . . ? C20 C11 C16 128.58(14) . . ? C12 C11 C16 105.29(12) . . ? O2 C12 C11 114.51(12) . . ? O2 C12 C13 111.18(12) . . ? C11 C12 C13 105.49(12) . . ? O2 C12 C17 118.85(12) . . ? C11 C12 C17 101.84(11) . . ? C13 C12 C17 103.53(12) . . ? C12 C13 C14 102.68(13) . . ? C15 C14 C13 103.17(13) . . ? C14 C15 C17 103.33(13) . . ? C14 C15 C16 105.84(15) . . ? C17 C15 C16 102.48(13) . . ? C11 C16 C15 101.75(12) . . ? C18 C17 C19 108.71(14) . . ? C18 C17 C15 114.17(14) . . ? C19 C17 C15 114.18(13) . . ? C18 C17 C12 113.69(14) . . ? C19 C17 C12 113.00(13) . . ? C15 C17 C12 92.50(11) . . ? C10 C1A C2A 132(2) . . ? C10 C1A C6 134(2) . . ? C2A C1A C6 90.5(10) . . ? O1 C2A C7A 112.6(9) . . ? O1 C2A C3A 114.0(9) . . ? C7A C2A C3A 104.3(9) . . ? O1 C2A C1A 108.7(10) . . ? C7A C2A C1A 103.7(11) . . ? C3A C2A C1A 113.1(13) . . ? C2A C3A C4A 102.8(9) . . ? C3A C4A C5 101.3(7) . . ? C5 C7A C8A 106.8(9) . . ? C5 C7A C2A 99.2(7) . . ? C8A C7A C2A 114.0(9) . . ? C5 C7A C9A 112.0(8) . . ? C8A C7A C9A 112.3(9) . . ? C2A C7A C9A 111.8(9) . . ? 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 C2A O1 C2 C1 -63.9(11) . . . . ? C2A O1 C2 C3 171.0(11) . . . . ? C2A O1 C2 C7 51.3(11) . . . . ? C10 C1 C2 O1 -22.9(3) . . . . ? C6 C1 C2 O1 159.86(17) . . . . ? C10 C1 C2 C3 106.7(3) . . . . ? C6 C1 C2 C3 -70.5(2) . . . . ? C10 C1 C2 C7 -146.4(3) . . . . ? C6 C1 C2 C7 36.4(2) . . . . ? O1 C2 C3 C4 -163.08(16) . . . . ? C1 C2 C3 C4 68.97(18) . . . . ? C7 C2 C3 C4 -36.72(17) . . . . ? C2 C3 C4 C5 0.64(19) . . . . ? C3 C4 C5 C7A 24.4(5) . . . . ? C3 C4 C5 C6 -72.41(17) . . . . ? C3 C4 C5 C7 35.80(18) . . . . ? C3 C4 C5 C4A 55.0(8) . . . . ? C10 C1 C6 C5 -179.2(3) . . . . ? C2 C1 C6 C5 -2.2(2) . . . . ? C10 C1 C6 C1A 2(8) . . . . ? C2 C1 C6 C1A 179(100) . . . . ? C7A C5 C6 C1 14.4(5) . . . . ? C7 C5 C6 C1 -33.6(2) . . . . ? C4 C5 C6 C1 72.72(19) . . . . ? C4A C5 C6 C1 -86.6(4) . . . . ? C7A C5 C6 C1A 14.6(10) . . . . ? C7 C5 C6 C1A -33.4(9) . . . . ? C4 C5 C6 C1A 72.9(9) . . . . ? C4A C5 C6 C1A -86.4(9) . . . . ? C7A C5 C7 C8 75.4(6) . . . . ? C6 C5 C7 C8 171.99(15) . . . . ? C4 C5 C7 C8 62.39(19) . . . . ? C4A C5 C7 C8 -107.2(5) . . . . ? C7A C5 C7 C9 -159.3(6) . . . . ? C6 C5 C7 C9 -62.76(18) . . . . ? C4 C5 C7 C9 -172.36(15) . . . . ? C4A C5 C7 C9 18.1(4) . . . . ? C7A C5 C7 C2 -42.8(6) . . . . ? C6 C5 C7 C2 53.74(15) . . . . ? C4 C5 C7 C2 -55.86(14) . . . . ? C4A C5 C7 C2 134.6(5) . . . . ? O1 C2 C7 C8 64.7(2) . . . . ? C1 C2 C7 C8 -173.15(18) . . . . ? C3 C2 C7 C8 -62.39(19) . . . . ? O1 C2 C7 C9 -58.8(2) . . . . ? C1 C2 C7 C9 63.4(2) . . . . ? C3 C2 C7 C9 174.13(15) . . . . ? O1 C2 C7 C5 -175.50(14) . . . . ? C1 C2 C7 C5 -53.31(16) . . . . ? C3 C2 C7 C5 57.45(14) . . . . ? C6 C1 C10 C1A -155(100) . . . . ? C2 C1 C10 C1A 28(100) . . . . ? C20 C11 C12 O2 -15.4(2) . . . . ? C16 C11 C12 O2 165.08(13) . . . . ? C20 C11 C12 C13 107.15(19) . . . . ? C16 C11 C12 C13 -72.35(15) . . . . ? C20 C11 C12 C17 -145.02(18) . . . . ? C16 C11 C12 C17 35.49(15) . . . . ? O2 C12 C13 C14 -163.82(14) . . . . ? C11 C12 C13 C14 71.49(16) . . . . ? C17 C12 C13 C14 -35.11(16) . . . . ? C12 C13 C14 C15 -0.12(19) . . . . ? C13 C14 C15 C17 35.36(18) . . . . ? C13 C14 C15 C16 -71.98(17) . . . . ? C20 C11 C16 C15 -179.30(18) . . . . ? C12 C11 C16 C15 0.18(17) . . . . ? C14 C15 C16 C11 71.99(16) . . . . ? C17 C15 C16 C11 -35.97(16) . . . . ? C14 C15 C17 C18 63.04(18) . . . . ? C16 C15 C17 C18 172.90(15) . . . . ? C14 C15 C17 C19 -171.01(14) . . . . ? C16 C15 C17 C19 -61.15(17) . . . . ? C14 C15 C17 C12 -54.37(15) . . . . ? C16 C15 C17 C12 55.48(14) . . . . ? O2 C12 C17 C18 60.45(19) . . . . ? C11 C12 C17 C18 -172.72(14) . . . . ? C13 C12 C17 C18 -63.39(16) . . . . ? O2 C12 C17 C19 -64.07(17) . . . . ? C11 C12 C17 C19 62.75(14) . . . . ? C13 C12 C17 C19 172.09(12) . . . . ? O2 C12 C17 C15 178.28(13) . . . . ? C11 C12 C17 C15 -54.90(13) . . . . ? C13 C12 C17 C15 54.44(13) . . . . ? C1 C10 C1A C2A 179(100) . . . . ? C1 C10 C1A C6 24(99) . . . . ? C1 C6 C1A C10 -177(100) . . . . ? C5 C6 C1A C10 -179(2) . . . . ? C1 C6 C1A C2A 21(7) . . . . ? C5 C6 C1A C2A 19.8(13) . . . . ? C2 O1 C2A C7A -33.0(7) . . . . ? C2 O1 C2A C3A -151.5(17) . . . . ? C2 O1 C2A C1A 81.3(14) . . . . ? C10 C1A C2A O1 32(3) . . . . ? C6 C1A C2A O1 -165.8(9) . . . . ? C10 C1A C2A C7A 152(2) . . . . ? C6 C1A C2A C7A -45.8(12) . . . . ? C10 C1A C2A C3A -96(3) . . . . ? C6 C1A C2A C3A 66.6(13) . . . . ? O1 C2A C3A C4A 158.4(8) . . . . ? C7A C2A C3A C4A 35.3(11) . . . . ? C1A C2A C3A C4A -76.7(13) . . . . ? C2A C3A C4A C5 -4.5(10) . . . . ? C7A C5 C4A C3A -29.7(8) . . . . ? C6 C5 C4A C3A 75.0(7) . . . . ? C7 C5 C4A C3A -31.7(5) . . . . ? C4 C5 C4A C3A -55.1(12) . . . . ? C6 C5 C7A C8A 75.3(8) . . . . ? C7 C5 C7A C8A 171.1(11) . . . . ? C4 C5 C7A C8A -24.3(6) . . . . ? C4A C5 C7A C8A 168.9(8) . . . . ? C6 C5 C7A C2A -43.4(7) . . . . ? C7 C5 C7A C2A 52.5(6) . . . . ? C4 C5 C7A C2A -143.0(8) . . . . ? C4A C5 C7A C2A 50.3(8) . . . . ? C6 C5 C7A C9A -161.5(6) . . . . ? C7 C5 C7A C9A -65.6(7) . . . . ? C4 C5 C7A C9A 98.9(8) . . . . ? C4A C5 C7A C9A -67.8(8) . . . . ? O1 C2A C7A C5 178.5(7) . . . . ? C3A C2A C7A C5 -57.5(9) . . . . ? C1A C2A C7A C5 61.1(12) . . . . ? O1 C2A C7A C8A 65.4(12) . . . . ? C3A C2A C7A C8A -170.6(9) . . . . ? C1A C2A C7A C8A -52.0(15) . . . . ? O1 C2A C7A C9A -63.3(11) . . . . ? C3A C2A C7A C9A 60.8(11) . . . . ? C1A C2A C7A C9A 179.4(12) . . . . ? 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 O2 0.74(2) 1.97(3) 2.7076(15) 169(3) 5_645 O2 H2 O1 0.79(2) 1.96(2) 2.6956(16) 154(2) . _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 33.14 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.24 _refine_diff_density_min -0.19 _refine_diff_density_rms 0.039 #===============================END=========================================