# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 188/249 #============================================================================= data_global #============================================================================= # 0. AUDIT DETAILS _audit_creation_date 'Oct 7 16:40:33 1999' _audit_creation_method 'PLATON option' _audit_update_record ; ? ; #============================================================================= # 1. SUBMISSION DETAILS _publ_contact_author ; Dr Mirjana Eckert-Maksi\'c Rudjer Bo\2sigma(I) _computing_data_collection 'EXPRESS-CAD4 (Enraf Nonius 1992) software' _computing_cell_refinement 'CAD4 (Enraf Nonius 1988) software routine' _computing_data_reduction 'HELENA (Spek, 1994)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; PLATON99 (Spek, 1982-1999) & ORTEP (Johnson, 1965) ; _computing_publication_material 'PLATON99 (Spek, 1982-1999)' #============================================================================= # 8. REFINEMENT DATA _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 w=1/[\s^2^(Fo^2^)+(0.0805P)^2^+0.2742P] 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 'refall' _refine_ls_extinction_method 'none' _refine_ls_extinction_coef ? _refine_ls_extinction_expression ? _refine_ls_abs_structure_details ; ? ; _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 1600 _refine_ls_number_parameters 157 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_all 0.0785 _refine_ls_R_factor_gt 0.0486 _refine_ls_wR_factor_ref 0.1297 _refine_ls_wR_factor_gt 0.1215 _refine_ls_goodness_of_fit_ref 0.948 _refine_ls_restrained_S_all 0.948 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.226 _refine_diff_density_min -0.286 _refine_diff_density_rms 0.059 #============================================================================= # 9. ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group O9 O Uani 0.37798(16) 0.9540(3) 0.12931(7) 1 0.0215(4) d . . O10 O Uani 0.68410(17) 1.0522(3) 0.06813(7) 1 0.0217(4) d . . C1 C Uani 0.6702(2) 0.8029(4) 0.03871(10) 1 0.0213(6) d . . C2 C Uani 0.8566(3) 0.7168(4) 0.04397(10) 1 0.0274(6) d . . C3 C Uani 0.9254(3) 0.8469(5) 0.11343(10) 1 0.0279(6) d . . C4 C Uani 0.7652(2) 0.9815(4) 0.13569(10) 1 0.0233(6) d . . C4A C Uani 0.6440(2) 0.7867(4) 0.16442(10) 1 0.0212(5) d . . C5 C Uani 0.4756(2) 0.8842(4) 0.19339(10) 1 0.0227(5) d . . C6 C Uani 0.3803(3) 0.6522(4) 0.21569(10) 1 0.0262(6) d . . C7 C Uani 0.3227(3) 0.5458(4) 0.15544(10) 1 0.0261(6) d . . C8 C Uani 0.3812(2) 0.7106(4) 0.09650(10) 1 0.0217(5) d . . C8A C Uani 0.5745(2) 0.6587(4) 0.09382(10) 1 0.0207(5) d . . H1 H Uiso 0.616(2) 0.807(4) -0.0099(10) 1 0.012(5) d . . H4 H Uiso 0.778(3) 1.121(5) 0.1652(11) 1 0.024(6) d . . H4A H Uiso 0.710(3) 0.681(4) 0.1984(11) 1 0.022(6) d . . H5 H Uiso 0.485(3) 1.022(5) 0.2255(12) 1 0.031(6) d . . H6 H Uiso 0.384(3) 0.599(5) 0.2628(14) 1 0.036(7) d . . H7 H Uiso 0.269(3) 0.391(6) 0.1500(12) 1 0.038(7) d . . H8 H Uiso 0.315(3) 0.711(4) 0.0490(10) 1 0.017(5) d . . H8A H Uiso 0.596(3) 0.483(5) 0.0901(11) 1 0.020(5) d . . H21 H Uiso 0.916(3) 0.779(5) 0.0026(13) 1 0.037(7) d . . H22 H Uiso 0.870(3) 0.530(6) 0.0441(13) 1 0.046(8) d . . H31 H Uiso 0.972(3) 0.739(5) 0.1524(13) 1 0.036(7) d . . H32 H Uiso 1.015(4) 0.968(6) 0.1048(13) 1 0.046(8) 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 O9 0.0219(7) 0.0202(7) 0.0222(7) -0.0030(6) -0.0001(5) 0.0039(5) O10 0.0266(7) 0.0191(7) 0.0192(6) -0.0023(5) -0.0003(5) 0.0003(5) C1 0.0259(10) 0.0199(10) 0.0180(9) -0.0004(7) 0.0018(7) 0.0032(8) C2 0.0279(10) 0.0298(11) 0.0251(10) -0.0006(9) 0.0068(8) 0.0038(9) C3 0.0207(9) 0.0375(12) 0.0256(10) 0.0025(9) 0.0023(8) 0.0018(9) C4 0.0235(10) 0.0256(11) 0.0203(9) -0.0037(8) -0.0017(7) 0.0003(8) C4A 0.0221(9) 0.0247(10) 0.0168(9) 0.0006(8) 0.0001(7) 0.0057(8) C5 0.0245(9) 0.0243(10) 0.0195(9) -0.0040(8) 0.0020(7) 0.0025(8) C6 0.0241(9) 0.0300(11) 0.0251(10) 0.0048(9) 0.0057(7) 0.0063(9) C7 0.0220(9) 0.0248(11) 0.0320(11) 0.0036(9) 0.0053(8) 0.0020(9) C8 0.0243(9) 0.0184(10) 0.0222(9) -0.0023(8) -0.0004(7) 0.0020(8) C8A 0.0250(9) 0.0181(9) 0.0189(9) -0.0014(8) 0.0016(7) 0.0046(8) #=========================================================================== # 10. MOLECULAR GEOMETRY _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All esds are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O9 C5 1.440(2) . . yes O9 C8 1.444(3) . . yes O10 C1 1.448(3) . . yes O10 C4 1.439(2) . . yes C1 C2 1.536(3) . . yes C1 C8A 1.531(3) . . yes C2 C3 1.551(3) . . yes C3 C4 1.534(3) . . yes C4 C4A 1.536(3) . . yes C4A C5 1.556(3) . . yes C4A C8A 1.565(3) . . yes C5 C6 1.525(3) . . yes C6 C7 1.325(3) . . yes C7 C8 1.514(3) . . yes C8 C8A 1.551(3) . . yes C1 H1 0.987(19) . . no C2 H21 0.99(2) . . no C2 H22 1.01(3) . . no C3 H31 0.99(3) . . no C3 H32 0.98(3) . . no C4 H4 0.93(2) . . no C4A H4A 0.98(2) . . no C5 H5 0.95(3) . . no C6 H6 0.93(3) . . no C7 H7 0.93(3) . . no C8 H8 1.01(2) . . no C8A H8A 0.96(3) . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 O9 C8 95.86(15) . . . yes C1 O10 C4 96.60(15) . . . yes O10 C1 C2 101.75(15) . . . yes O10 C1 C8A 103.53(15) . . . yes C2 C1 C8A 108.30(16) . . . yes C1 C2 C3 101.58(17) . . . yes C2 C3 C4 101.14(18) . . . yes O10 C4 C3 101.99(15) . . . yes O10 C4 C4A 103.91(14) . . . yes C3 C4 C4A 108.48(18) . . . yes C4 C4A C5 117.25(18) . . . no C4 C4A C8A 100.90(15) . . . yes C5 C4A C8A 100.72(14) . . . yes O9 C5 C4A 102.35(14) . . . yes O9 C5 C6 101.39(15) . . . yes C4A C5 C6 105.56(17) . . . yes C5 C6 C7 105.18(17) . . . yes C6 C7 C8 105.97(19) . . . yes O9 C8 C7 101.40(15) . . . yes O9 C8 C8A 102.69(15) . . . yes C7 C8 C8A 105.31(17) . . . yes C1 C8A C4A 101.29(15) . . . no C1 C8A C8 117.24(16) . . . yes C4A C8A C8 100.64(15) . . . yes O10 C1 H1 110.7(13) . . . no C2 C1 H1 115.0(10) . . . no C8A C1 H1 116.1(11) . . . no C1 C2 H21 110.1(14) . . . no C1 C2 H22 113.5(14) . . . no C3 C2 H21 110.9(15) . . . no C3 C2 H22 114.5(14) . . . no H21 C2 H22 106(2) . . . no C2 C3 H31 117.3(15) . . . no C2 C3 H32 112.0(15) . . . no C4 C3 H31 110.2(14) . . . no C4 C3 H32 110.3(19) . . . no H31 C3 H32 106(2) . . . no O10 C4 H4 110.0(14) . . . no C3 C4 H4 118.7(15) . . . no C4A C4 H4 112.3(14) . . . no C4 C4A H4A 107.9(14) . . . no C5 C4A H4A 113.1(13) . . . no C8A C4A H4A 116.5(13) . . . no O9 C5 H5 110.3(15) . . . no C4A C5 H5 116.7(14) . . . no C6 C5 H5 118.4(15) . . . no C5 C6 H6 121.7(16) . . . no C7 C6 H6 132.4(16) . . . no C6 C7 H7 127.2(14) . . . no C8 C7 H7 126.4(14) . . . no O9 C8 H8 110.9(12) . . . no C7 C8 H8 119.3(13) . . . no C8A C8 H8 115.1(13) . . . no C1 C8A H8A 110.4(13) . . . no C4A C8A H8A 116.0(13) . . . no C8 C8A H8A 110.9(14) . . . no 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 C8 O9 C5 C4A 58.07(16) . . . . no C5 O9 C8 C7 50.76(15) . . . . no C5 O9 C8 C8A -58.00(15) . . . . no C8 O9 C5 C6 -50.84(16) . . . . no C4 O10 C1 C2 -57.10(15) . . . . no C1 O10 C4 C4A -55.01(16) . . . . no C1 O10 C4 C3 57.72(17) . . . . no C4 O10 C1 C8A 55.22(15) . . . . no C2 C1 C8A C4A 73.40(19) . . . . no C8A C1 C2 C3 -74.5(2) . . . . no C2 C1 C8A C8 -178.27(17) . . . . yes O10 C1 C2 C3 34.22(18) . . . . yes O10 C1 C8A C8 74.26(19) . . . . no O10 C1 C8A C4A -34.07(16) . . . . yes C1 C2 C3 C4 0.6(2) . . . . yes C2 C3 C4 O10 -35.5(2) . . . . yes C2 C3 C4 C4A 73.76(19) . . . . no C3 C4 C4A C5 177.34(16) . . . . no C3 C4 C4A C8A -74.46(17) . . . . yes O10 C4 C4A C8A 33.51(18) . . . . yes O10 C4 C4A C5 -74.70(19) . . . . no C4 C4A C8A C1 0.48(19) . . . . yes C4 C4A C8A C8 -120.34(16) . . . . no C4 C4A C5 C6 178.29(16) . . . . no C8A C4A C5 C6 69.98(18) . . . . yes C8A C4A C5 O9 -35.73(19) . . . . yes C5 C4A C8A C8 0.40(19) . . . . yes C4 C4A C5 O9 72.6(2) . . . . no C5 C4A C8A C1 121.22(16) . . . . no O9 C5 C6 C7 32.8(2) . . . . yes C4A C5 C6 C7 -73.6(2) . . . . no C5 C6 C7 C8 -0.2(2) . . . . yes C6 C7 C8 C8A 74.3(2) . . . . no C6 C7 C8 O9 -32.4(2) . . . . yes C7 C8 C8A C4A -70.81(19) . . . . yes O9 C8 C8A C4A 34.95(18) . . . . yes O9 C8 C8A C1 -73.76(19) . . . . no C7 C8 C8A C1 -179.52(17) . . . . no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag O9 O10 2.787(3) . . no O9 C7 3.243(4) . 1_565 no O10 O9 2.787(3) . . no O10 C8A 3.405(4) . 1_565 no O10 C8 3.364(3) . 3_675 no O9 H1 2.59(2) . 3_675 no O9 H32 2.87(3) . 1_455 no O9 H7 2.53(3) . 1_565 no O10 H8A 2.45(3) . 1_565 no O10 H1 2.651(17) . 3_675 no O10 H8 2.55(2) . 3_675 no C3 C7 3.564(4) . 1_655 no C7 C3 3.564(4) . 1_455 no C7 O9 3.243(4) . 1_545 no C8 O10 3.364(3) . 3_675 no C8A O10 3.405(4) . 1_545 no C1 H8 3.09(2) . 3_675 no C1 H1 3.096(19) . 3_675 no C2 H22 3.10(3) . 3_765 no C3 H6 3.01(3) . 2_655 no C4 H8A 3.10(3) . 1_565 no C7 H31 2.95(2) . 1_455 no C8 H1 3.06(2) . 3_675 no H1 O9 2.59(2) . 3_675 no H1 O10 2.651(17) . 3_675 no H1 C1 3.096(19) . 3_675 no H1 C8 3.06(2) . 3_675 no H4 H4A 2.59(3) . 2_655 no H4A H31 2.31(3) . . no H4A H4 2.59(3) . 2_645 no H5 H31 2.58(3) . 2_655 no H6 C3 3.01(3) . 2_645 no H7 O9 2.53(3) . 1_545 no H8 O10 2.55(2) . 3_675 no H8 C1 3.09(2) . 3_675 no H8 H22 2.56(3) . 3_665 no H8A O10 2.45(3) . 1_545 no H8A C4 3.10(3) . 1_545 no H8A H22 2.39(3) . . no H21 H22 2.56(4) . 3_765 no H21 H32 2.52(4) . 3_775 no H22 H8A 2.39(3) . . no H22 C2 3.10(3) . 3_765 no H22 H8 2.56(3) . 3_665 no H22 H21 2.56(4) . 3_765 no H31 C7 2.95(2) . 1_655 no H31 H4A 2.31(3) . . no H31 H5 2.58(3) . 2_645 no H32 O9 2.87(3) . 1_655 no H32 H21 2.52(4) . 3_775 no 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 _geom_hbond_publ_flag # #D H A D - H H...A D...A D - H...A symm(A) # C1 H1 O9 0.987(19) 2.59(2) 3.425(3) 141.9(15) 3_675 no C7 H7 O9 0.93(3) 2.53(3) 3.243(4) 133.1(19) 1_545 no C8 H8 O10 1.01(2) 2.55(2) 3.364(3) 137.9(17) 3_675 no C8A H8A O10 0.96(3) 2.45(3) 3.405(4) 171.2(19) 1_545 no #===END======================================================================= data_OXANORBORNENE2 #============================================================================= # 5. CHEMICAL DATA _chemical_name_systematic ; endo-exo-1,4:5,8-diepoxy-1,23,4a,5,8,8a-octahydronaphthalene ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C10 H12 O2' _chemical_formula_weight 164.20 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0492 0.0322 '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' C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #============================================================================= # 6. CRYSTAL DATA _symmetry_cell_setting 'monoclinic' _symmetry_space_group_name_Hall '-P 2yab' _symmetry_space_group_name_H-M 'P 21/a' loop_ _symmetry_equiv_pos_as_xyz 'x,y,z' '1/2-x,1/2+y,-z' '-x,-y,-z' '1/2+x,1/2-y,z' _cell_length_a 6.517(7) _cell_length_b 18.98(1) _cell_length_c 6.754(8) _cell_angle_alpha 90.0 _cell_angle_beta 107.16(6) _cell_angle_gamma 90.0 _cell_volume 798.1(14) _cell_formula_units_Z 4 _cell_measurement_temperature 100(3) _cell_measurement_reflns_used 25 _cell_measurement_theta_max 22 _cell_measurement_theta_min 8 _cell_special_details ; ? ; _exptl_crystal_description 'prism' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.367 _exptl_crystal_density_method ? _exptl_crystal_F_000 352 _exptl_absorpt_coefficient_mu 0.094 _exptl_crystal_density_meas_temp ? _exptl_absorpt_correction_type 'none' _exptl_absorpt_correction_T_max ? _exptl_absorpt_correction_T_min ? #============================================================================= # 7. EXPERIMENTAL DATA _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(3) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'fine-focused sealed tube' _diffrn_radiation_monochromator 'graphite' _diffrn_measurement_device_type 'Enraf-Nonius CAD4 diffractometer' _diffrn_measurement_method '\w/2\q' _diffrn_standards_number 3 _diffrn_standards_interval_count 75 _diffrn_standards_interval_time 120 _diffrn_standards_decay_% ? loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l -2 6 0 -2 1 -2 -2 -1 -2 _diffrn_reflns_number 2076 _diffrn_reflns_av_R_equivalents 0.0423 _diffrn_reflns_av_sigmaI/netI 0.0807 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 27.98 _diffrn_reflns_reduction_process ; ? ; _diffrn_measured_fraction_theta_max 0.948 _diffrn_reflns_theta_full 27.98 _diffrn_measured_fraction_theta_full 0.948 _reflns_number_total 1878 _reflns_number_gt 1123 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'EXPRESS-CAD4 (Enraf Nonius 1992) software' _computing_cell_refinement 'CAD4 (Enraf Nonius 1988) software routine' _computing_data_reduction 'HELENA (Spek, 1994)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1985, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; PLATON99 (Spek, 1982-1999) & ORTEP (Johnson, 1965) ; _computing_publication_material 'PLATON99 (Spek, 1982-1999)' #============================================================================= # 8. REFINEMENT DATA _refine_special_details ; Refinement on F^2^ for ALL reflections except for 475 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating R-factor-obs 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 w=1/[\s^2^(Fo^2^)+(0.0896P)^2^+0.1813P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary 'direct' _atom_sites_solution_secondary 'difmap' _atom_sites_solution_hydrogens 'difmap' _refine_ls_hydrogen_treatment 'refall' _refine_ls_extinction_method 'none' _refine_ls_extinction_coef ? _refine_ls_extinction_expression ? _refine_ls_abs_structure_details ; ? ; _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 1878 _refine_ls_number_parameters 157 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_all 0.1324 _refine_ls_R_factor_gt 0.0611 _refine_ls_wR_factor_ref 0.1884 _refine_ls_wR_factor_gt 0.1480 _refine_ls_goodness_of_fit_ref 1.129 _refine_ls_restrained_S_all 1.129 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0.001 _refine_diff_density_max 0.438 _refine_diff_density_min -0.468 _refine_diff_density_rms 0.104 #============================================================================= # 9. ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group O9 O Uani 0.5426(3) 0.08267(11) 0.4768(2) 1 0.0181(6) d . . O10 O Uani 0.7102(3) 0.16339(11) 1.0300(3) 1 0.0198(6) d . . C1 C Uani 0.7994(5) 0.17116(17) 0.8572(4) 1 0.0189(9) d . . C2 C Uani 0.8975(5) 0.09856(17) 0.8472(4) 1 0.0200(9) d . . C3 C Uani 0.7364(5) 0.05034(17) 0.9129(4) 1 0.0209(9) d . . C4 C Uani 0.5737(5) 0.10363(16) 0.9447(4) 1 0.0172(8) d . . C5 C Uani 0.3507(5) 0.08933(17) 0.5427(4) 1 0.0202(9) d . . C6 C Uani 0.2146(5) 0.13852(19) 0.3769(4) 1 0.0263(10) d . . C7 C Uani 0.3526(5) 0.17991(18) 0.3233(4) 1 0.0241(9) d . . C8 C Uani 0.5746(5) 0.15727(16) 0.4566(4) 1 0.0192(8) d . . C4A C Uani 0.4308(4) 0.13562(16) 0.7406(4) 1 0.0170(8) d . . C8A C Uani 0.5950(5) 0.18488(16) 0.6771(4) 1 0.0177(8) d . . H1 H Uiso 0.900(5) 0.2121(16) 0.890(5) 1 0.014(7) d . . H4 H Uiso 0.482(6) 0.0911(19) 1.041(6) 1 0.031(10) d . . H5 H Uiso 0.290(6) 0.043(2) 0.553(5) 1 0.035(10) d . . H6 H Uiso 0.053(6) 0.1415(17) 0.342(5) 1 0.025(9) d . . H7 H Uiso 0.322(6) 0.221(2) 0.226(6) 1 0.045(11) d . . H8 H Uiso 0.697(5) 0.1642(17) 0.392(5) 1 0.019(8) d . . H21 H Uiso 1.036(5) 0.0948(15) 0.955(5) 1 0.012(7) d . . H22 H Uiso 0.907(5) 0.0910(16) 0.703(5) 1 0.021(8) d . . H31 H Uiso 0.801(5) 0.0279(18) 1.050(5) 1 0.023(9) d . . H32 H Uiso 0.667(5) 0.0157(18) 0.800(5) 1 0.023(9) d . . H4A H Uiso 0.307(5) 0.1647(16) 0.771(5) 1 0.013(7) d . . H8A H Uiso 0.556(5) 0.2372(18) 0.673(5) 1 0.022(8) 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 O9 0.0189(10) 0.0183(11) 0.0161(10) -0.0018(8) 0.0038(8) 0.0011(9) O10 0.0205(11) 0.0273(12) 0.0116(9) -0.0022(8) 0.0047(8) -0.0030(9) C1 0.0180(14) 0.0267(18) 0.0119(13) 0.0005(12) 0.0041(11) -0.0033(13) C2 0.0142(14) 0.0277(17) 0.0158(14) -0.0006(12) 0.0009(11) 0.0010(12) C3 0.0201(15) 0.0232(17) 0.0162(14) 0.0020(12) 0.0004(12) -0.0013(13) C4 0.0173(14) 0.0221(16) 0.0116(13) -0.0002(11) 0.0035(11) -0.0027(12) C5 0.0200(15) 0.0241(17) 0.0145(14) -0.0016(12) 0.0020(11) -0.0023(13) C6 0.0217(16) 0.038(2) 0.0151(14) -0.0039(13) -0.0007(12) 0.0099(14) C7 0.0291(17) 0.0285(18) 0.0125(14) 0.0001(12) 0.0029(12) 0.0072(13) C8 0.0231(15) 0.0200(16) 0.0138(13) -0.0001(11) 0.0045(12) -0.0004(12) C4A 0.0133(13) 0.0234(16) 0.0143(13) -0.0018(11) 0.0039(11) -0.0017(12) C8A 0.0209(15) 0.0199(16) 0.0140(13) -0.0014(11) 0.0079(11) 0.0004(13) #============================================================================= # 10. MOLECULAR GEOMETRY _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All esds are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O9 C5 1.451(4) . . yes O9 C8 1.443(4) . . yes O10 C1 1.457(4) . . yes O10 C4 1.452(4) . . yes C1 C2 1.529(5) . . yes C1 C8A 1.538(5) . . yes C2 C3 1.553(5) . . yes C3 C4 1.526(5) . . yes C4 C4A 1.542(4) . . yes C5 C6 1.525(5) . . yes C5 C4A 1.555(4) . . yes C6 C7 1.322(5) . . yes C7 C8 1.523(5) . . yes C8 C8A 1.547(4) . . yes C4A C8A 1.573(5) . . yes C1 H1 1.00(3) . . no C2 H21 0.98(3) . . no C2 H22 1.00(3) . . no C3 H31 0.99(3) . . no C3 H32 1.01(3) . . no C4 H4 1.03(4) . . no C5 H5 0.97(4) . . no C6 H6 1.01(4) . . no C7 H7 1.00(4) . . no C8 H8 1.02(3) . . no C4A H4A 1.05(3) . . no C8A H8A 1.02(3) . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 O9 C8 96.0(2) . . . yes C1 O10 C4 96.0(2) . . . yes O10 C1 C2 102.4(2) . . . yes O10 C1 C8A 101.2(2) . . . yes C2 C1 C8A 113.2(2) . . . yes C1 C2 C3 101.0(3) . . . yes C2 C3 C4 101.9(3) . . . yes O10 C4 C3 101.8(3) . . . yes O10 C4 C4A 100.7(2) . . . yes C3 C4 C4A 113.4(2) . . . yes O9 C5 C6 101.3(2) . . . yes O9 C5 C4A 102.2(2) . . . yes C6 C5 C4A 105.1(3) . . . yes C5 C6 C7 105.6(3) . . . yes C6 C7 C8 105.9(3) . . . yes O9 C8 C7 101.2(2) . . . yes O9 C8 C8A 102.4(2) . . . yes C7 C8 C8A 105.7(3) . . . yes C4 C4A C5 120.5(3) . . . yes C4 C4A C8A 101.4(2) . . . yes C5 C4A C8A 100.6(2) . . . yes C1 C8A C8 120.8(3) . . . yes C1 C8A C4A 100.6(2) . . . yes C8 C8A C4A 100.9(2) . . . yes O10 C1 H1 107.0(19) . . . no C2 C1 H1 117.1(19) . . . no C8A C1 H1 113.7(19) . . . no C1 C2 H21 109.8(17) . . . no C1 C2 H22 108.5(18) . . . no C3 C2 H21 107.3(19) . . . no C3 C2 H22 115.7(19) . . . no H21 C2 H22 114(3) . . . no C2 C3 H31 113(2) . . . no C2 C3 H32 111.0(19) . . . no C4 C3 H31 106(2) . . . no C4 C3 H32 111(2) . . . no H31 C3 H32 113(3) . . . no O10 C4 H4 109(2) . . . no C3 C4 H4 119(2) . . . no C4A C4 H4 110(2) . . . no O9 C5 H5 110(2) . . . no C6 C5 H5 116(2) . . . no C4A C5 H5 119.2(19) . . . no C5 C6 H6 123.1(19) . . . no C7 C6 H6 130.5(19) . . . no C6 C7 H7 128(2) . . . no C8 C7 H7 125(2) . . . no O9 C8 H8 108.6(18) . . . no C7 C8 H8 115.8(18) . . . no C8A C8 H8 120.7(18) . . . no C4 C4A H4A 109.2(18) . . . no C5 C4A H4A 112.6(18) . . . no C8A C4A H4A 111.5(17) . . . no C1 C8A H8A 109.6(19) . . . no C8 C8A H8A 110.6(18) . . . no C4A C8A H8A 113.6(19) . . . no 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 C5 O9 C8 C8A 58.3(2) . . . . no C8 O9 C5 C6 50.4(2) . . . . no C8 O9 C5 C4A -57.9(2) . . . . no C5 O9 C8 C7 -50.7(2) . . . . no C4 O10 C1 C8A 60.0(3) . . . . no C1 O10 C4 C3 57.4(2) . . . . no C1 O10 C4 C4A -59.5(2) . . . . no C4 O10 C1 C2 -57.0(3) . . . . no O10 C1 C2 C3 34.2(3) . . . . no C2 C1 C8A C8 -36.9(4) . . . . no C2 C1 C8A C4A 72.7(3) . . . . no O10 C1 C8A C8 -145.8(3) . . . . no O10 C1 C8A C4A -36.2(3) . . . . no C8A C1 C2 C3 -73.9(3) . . . . no C1 C2 C3 C4 1.0(3) . . . . no C2 C3 C4 O10 -35.9(2) . . . . no C2 C3 C4 C4A 71.3(3) . . . . no C3 C4 C4A C5 37.8(4) . . . . no O10 C4 C4A C8A 36.0(3) . . . . no C3 C4 C4A C8A -71.9(3) . . . . no O10 C4 C4A C5 145.7(3) . . . . no O9 C5 C4A C4 -75.2(3) . . . . no O9 C5 C6 C7 -31.9(3) . . . . no C6 C5 C4A C8A -70.5(3) . . . . no C6 C5 C4A C4 179.4(3) . . . . no O9 C5 C4A C8A 34.9(3) . . . . no C4A C5 C6 C7 74.2(3) . . . . no C5 C6 C7 C8 -0.6(3) . . . . no C6 C7 C8 O9 33.0(3) . . . . no C6 C7 C8 C8A -73.4(3) . . . . no O9 C8 C8A C1 73.7(3) . . . . no C7 C8 C8A C1 179.3(3) . . . . no C7 C8 C8A C4A 69.8(3) . . . . no O9 C8 C8A C4A -35.7(3) . . . . no C5 C4A C8A C8 0.3(3) . . . . no C5 C4A C8A C1 -124.2(2) . . . . no C4 C4A C8A C1 0.1(3) . . . . no C4 C4A C8A C8 124.7(2) . . . . no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag O9 C2 2.878(5) . . no O9 C3 2.907(5) . . no O9 O9 3.218(5) . 3_656 no O9 C5 3.348(6) . 3_656 no O10 C8 3.256(5) . 1_556 no O9 H32 2.45(3) . . no O9 H22 2.42(3) . . no O9 H5 2.65(4) . 3_656 no O9 H32 2.71(3) . 3_656 no O9 H4 2.86(4) . 1_554 no O10 H6 2.61(4) . 1_656 no O10 H8 2.47(3) . 1_556 no O10 H7 2.55(4) . 4_556 no C2 O9 2.878(5) . . no C2 C5 3.554(6) . . no C3 O9 2.907(5) . . no C3 C8 3.579(6) . . no C4 C7 3.589(6) . 1_556 no C5 O9 3.348(6) . 3_656 no C5 C2 3.554(6) . . no C7 C4 3.589(6) . 1_554 no C8 O10 3.256(5) . 1_554 no C8 C3 3.579(6) . . no C1 H8A 2.93(3) . 4_555 no C2 H3A 3.05(3) . 3_757 no C3 H4 3.10(4) . 3_657 no C5 H32 3.03(3) . 3_656 no C5 H32 2.67(3) . . no C6 H21 2.86(3) . 1_454 no C7 H4 2.85(4) . 1_554 no C8 H4 2.97(4) . 1_554 no C8 H22 2.63(3) . . no C4A H1 3.09(3) . 4_455 no C8A H1 2.93(3) . 4_455 no H1 C4A 3.09(3) . 4_555 no H1 C8A 2.93(3) . 4_555 no H1 H4A 2.49(4) . 4_555 no H1 H8A 2.23(5) . 4_555 no H4 O9 2.86(4) . 1_556 no H4 C7 2.85(4) . 1_556 no H4 C8 2.97(4) . 1_556 no H4 C3 3.10(4) . 3_657 no H5 H32 2.58(5) . . no H5 O9 2.65(4) . 3_656 no H6 O10 2.61(4) . 1_454 no H6 H8 2.48(5) . 1_455 no H7 O10 2.55(4) . 4_454 no H8 O10 2.47(3) . 1_554 no H8 H6 2.48(5) . 1_655 no H8 H22 2.55(5) . . no H21 C6 2.86(3) . 1_656 no H21 H31 2.56(5) . 3_757 no H22 O9 2.42(3) . . no H22 C8 2.63(3) . . no H22 H8 2.55(5) . . no H31 C2 3.05(3) . 3_757 no H31 H21 2.56(5) . 3_757 no H32 O9 2.45(3) . . no H32 C5 2.67(3) . . no H32 H5 2.58(5) . . no H32 O9 2.71(3) . 3_656 no H32 C5 3.03(3) . 3_656 no H4A H1 2.49(4) . 4_455 no H4A H8A 2.44(5) . 4_455 no H8A C1 2.93(3) . 4_455 no H8A H1 2.23(5) . 4_455 no H8A H4A 2.44(5) . 4_555 no 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 _geom_hbond_publ_flag # #D H A D - H H...A D...A D - H...A symm(A) # C7 H7 O10 1.00(4) 2.55(4) 3.542(6) 169(3) 4_454 no C8 H8 O10 1.02(3) 2.47(3) 3.256(5) 133(2) 1_554 no C2 H22 O9 1.00(3) 2.42(3) 2.878(5) 107(2) . no C3 H32 O9 1.01(3) 2.45(3) 2.907(5) 107(2) . no #===END=======================================================================