Supplementary data for CrystEngComm This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'G. Mehta' _publ_contact_author_address ; Department of Organic Chemistry Indian Institute of Science Bangalore 560 012 INDIA ; _publ_contact_author_email GM@ORGCHEM.IISC.ERNET.IN _publ_section_title ; Understanding the self-assembling process in crystalline cyclooctitols: an insight into the conformational flexibility of medium sized rings ; loop_ _publ_author_name 'G. Mehta' 'Kotapalli Pallavi' 'Saikat Sen' #=============================================================================== data_diol_1 _database_code_depnum_ccdc_archive 'CCDC 658130' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; (3aR*,4R*,9R*,9aS*)-9-(hydroxymethyl)-2,2-dimethyl- 3a,4,9,9a-tetrahydrocycloocta[d][1,3]dioxol-4-ol ; _chemical_name_common ; (3aR*,4R*,9R*,9aS*)-9-(hydroxymethyl)-2,2-dimethyl-3a,4,9,9a- tetrahydrocycloocta(d)(1,3)dioxol-4-ol ; _chemical_melting_point ? _chemical_formula_moiety 'C12 H18 O4' _chemical_formula_structural 'C12 H18 O4' _chemical_formula_sum 'C12 H18 O4' _chemical_formula_iupac 'C12 H18 O4' _chemical_absolute_configuration unk _chemical_formula_weight 226.26 _chemical_compound_source 'see text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0106 0.0060 '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 0.0033 0.0016 '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 'C -2yc' _symmetry_space_group_name_H-M 'C c' _symmetry_Int_Tables_number 9 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 x,-y,1/2+z 3 1/2+x,1/2+y,z 4 1/2+x,1/2-y,1/2+z _cell_length_a 7.894(2) _cell_length_b 21.662(6) _cell_length_c 7.747(2) _cell_angle_alpha 90 _cell_angle_beta 115.645(4) _cell_angle_gamma 90 _cell_volume 1194.2(5) _cell_formula_units_Z 4 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _cell_special_details ; ; _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.28 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.258 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 488 _exptl_absorpt_coefficient_mu 0.094 _exptl_crystal_density_meas_temp ? _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1997)' _exptl_absorpt_correction_T_min 0.9386 _exptl_absorpt_correction_T_max 0.9743 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_ambient_temperature 291(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? _diffrn_reflns_number 4755 _diffrn_reflns_av_R_equivalents 0.0221 _diffrn_reflns_av_sigmaI/netI 0.0204 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.88 _diffrn_reflns_theta_max 26.57 _diffrn_reflns_theta_full 26.57 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measured_fraction_theta_full 1.000 _diffrn_reflns_reduction_process ; ; _reflns_number_total 1257 _reflns_number_gt 1143 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement 'SMART (Bruker, 1998)' _computing_data_reduction 'SAINT (Bruker, 1998)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993)' _computing_publication_material 'PLATON (Spek, 2003)' #=============================================================================== # 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 _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0449P)^2^+0.1743P] 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 'see text' _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 1257 _refine_ls_number_parameters 155 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0404 _refine_ls_R_factor_gt 0.0364 _refine_ls_wR_factor_ref 0.0875 _refine_ls_wR_factor_gt 0.0855 _refine_ls_goodness_of_fit_ref 1.159 _refine_ls_restrained_S_all 1.158 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.163 _refine_diff_density_min -0.118 _refine_diff_density_rms 0.032 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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 1.0791(3) 0.30039(11) 0.4364(4) 0.0611(6) Uani 1 1 d . . . O2 O 0.6074(3) 0.38612(10) 0.2156(2) 0.0473(5) Uani 1 1 d . . . O3 O 0.4167(2) 0.37054(9) 0.3598(2) 0.0461(5) Uani 1 1 d . . . O4 O 0.4403(3) 0.26922(11) 0.6208(3) 0.0610(6) Uani 1 1 d . . . C1 C 0.8801(3) 0.36644(11) 0.5161(3) 0.0349(5) Uani 1 1 d . . . C2 C 0.6986(3) 0.33999(12) 0.3589(3) 0.0375(6) Uani 1 1 d . . . C3 C 0.5453(3) 0.32020(12) 0.4190(4) 0.0389(6) Uani 1 1 d . . . C4 C 0.5993(3) 0.30262(13) 0.6254(4) 0.0406(6) Uani 1 1 d . . . C5 C 0.6558(4) 0.35059(14) 0.7816(4) 0.0480(7) Uani 1 1 d . . . C6 C 0.7229(4) 0.40770(13) 0.8030(4) 0.0516(7) Uani 1 1 d . . . C7 C 0.7795(4) 0.44705(12) 0.6858(4) 0.0474(7) Uani 1 1 d . . . C8 C 0.8512(4) 0.43088(12) 0.5665(3) 0.0404(6) Uani 1 1 d . . . C9 C 1.0384(4) 0.36313(14) 0.4533(4) 0.0448(6) Uani 1 1 d . . . C10 C 0.4175(4) 0.39336(15) 0.1886(4) 0.0477(7) Uani 1 1 d . . . C11 C 0.2883(5) 0.3562(2) 0.0151(4) 0.0731(11) Uani 1 1 d . . . C12 C 0.3679(5) 0.46060(17) 0.1730(6) 0.0738(10) Uani 1 1 d . . . H4O H 0.481(5) 0.2469(19) 0.722(5) 0.075(12) Uiso 1 1 d . . . H1O H 1.182(7) 0.2963(18) 0.484(6) 0.079(14) Uiso 1 1 d . . . H1 H 0.9155 0.3408 0.6307 0.042 Uiso 1 1 calc R . . H2 H 0.7305 0.3047 0.2992 0.045 Uiso 1 1 calc R . . H3 H 0.4806 0.2846 0.3398 0.047 Uiso 1 1 calc R . . H4 H 0.7035 0.2732 0.6627 0.049 Uiso 1 1 calc R . . H5 H 0.6399 0.3370 0.8875 0.058 Uiso 1 1 calc R . . H6 H 0.7363 0.4263 0.9164 0.062 Uiso 1 1 calc R . . H7 H 0.7633 0.4892 0.6958 0.057 Uiso 1 1 calc R . . H8 H 0.8869 0.4626 0.5085 0.049 Uiso 1 1 calc R . . H9A H 1.0006 0.3838 0.3312 0.054 Uiso 1 1 calc R . . H9B H 1.1495 0.3836 0.5468 0.054 Uiso 1 1 calc R . . H11A H 0.3310 0.3142 0.0292 0.110 Uiso 1 1 calc R . . H11B H 0.2896 0.3735 -0.0984 0.110 Uiso 1 1 calc R . . H11C H 0.1627 0.3573 0.0047 0.110 Uiso 1 1 calc R . . H12A H 0.2444 0.4654 0.1666 0.111 Uiso 1 1 calc R . . H12B H 0.3701 0.4773 0.0593 0.111 Uiso 1 1 calc R . . H12C H 0.4574 0.4821 0.2831 0.111 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0277(11) 0.0767(15) 0.0760(15) -0.0322(12) 0.0198(10) -0.0011(10) O2 0.0315(9) 0.0766(13) 0.0343(9) 0.0086(9) 0.0147(8) -0.0001(9) O3 0.0283(9) 0.0693(13) 0.0434(10) 0.0201(9) 0.0181(8) 0.0138(8) O4 0.0310(10) 0.0778(15) 0.0682(13) 0.0327(12) 0.0160(9) -0.0039(10) C1 0.0288(13) 0.0425(13) 0.0344(12) -0.0027(10) 0.0145(11) -0.0003(10) C2 0.0302(13) 0.0486(15) 0.0359(13) -0.0068(11) 0.0164(11) -0.0015(11) C3 0.0275(14) 0.0463(14) 0.0409(13) 0.0009(12) 0.0128(11) -0.0021(11) C4 0.0230(12) 0.0509(15) 0.0486(14) 0.0130(12) 0.0162(11) 0.0041(10) C5 0.0494(16) 0.0632(18) 0.0404(14) 0.0111(13) 0.0278(13) 0.0099(13) C6 0.0629(19) 0.0575(17) 0.0419(14) -0.0052(13) 0.0297(14) 0.0069(15) C7 0.0581(18) 0.0409(15) 0.0438(14) -0.0083(12) 0.0227(14) 0.0027(12) C8 0.0403(14) 0.0418(13) 0.0372(12) 0.0020(11) 0.0149(11) -0.0030(11) C9 0.0299(14) 0.0637(17) 0.0430(14) -0.0100(12) 0.0178(12) -0.0068(11) C10 0.0302(13) 0.0740(19) 0.0393(14) 0.0164(13) 0.0153(12) 0.0067(13) C11 0.0434(19) 0.120(3) 0.0429(16) 0.0079(18) 0.0063(15) -0.0103(19) C12 0.066(2) 0.083(2) 0.075(2) 0.0347(19) 0.0331(19) 0.0195(19) #=============================================================================== # 10. MOLECULAR GEOMETRY _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 C9 1.416(4) . ? O1 H1O 0.74(5) . ? O2 C2 1.434(3) . ? O2 C10 1.430(3) . ? O3 C3 1.424(3) . ? O3 C10 1.418(3) . ? O4 C4 1.436(3) . ? O4 H4O 0.86(4) . ? C1 C2 1.534(3) . ? C1 C9 1.526(3) . ? C1 H1 0.9800 . ? C2 H2 0.9800 . ? C3 C2 1.534(3) . ? C3 C4 1.514(4) . ? C3 H3 0.9800 . ? C4 C5 1.508(4) . ? C4 H4 0.9800 . ? C5 H5 0.9300 . ? C6 C5 1.328(4) . ? C6 C7 1.450(4) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 C1 1.493(4) . ? C8 C7 1.323(4) . ? C8 H8 0.9300 . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C12 1.500(5) . ? C11 C10 1.520(5) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? 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 C9 C1 108.9(2) . . ? O1 C9 H9A 109.9 . . ? O1 C9 H9B 109.9 . . ? O2 C2 C1 109.7(2) . . ? O2 C2 C3 103.40(19) . . ? O2 C2 H2 108.9 . . ? O2 C10 C11 109.3(3) . . ? O2 C10 C12 109.8(3) . . ? O3 C3 C2 103.6(2) . . ? O3 C3 C4 111.6(2) . . ? O3 C3 H3 107.2 . . ? O3 C10 O2 104.7(2) . . ? O3 C10 C11 111.7(2) . . ? O3 C10 C12 107.9(3) . . ? O4 C4 C3 104.9(2) . . ? O4 C4 C5 108.6(2) . . ? O4 C4 H4 107.0 . . ? C1 C2 C3 116.84(19) . . ? C1 C2 H2 108.9 . . ? C1 C8 H8 116.9 . . ? C1 C9 H9A 109.9 . . ? C1 C9 H9B 109.9 . . ? C2 C1 H1 108.0 . . ? C2 C3 H3 107.2 . . ? C3 C2 H2 108.9 . . ? C3 C4 H4 107.0 . . ? C4 O4 H4O 106(2) . . ? C4 C3 C2 119.5(2) . . ? C4 C3 H3 107.2 . . ? C4 C5 H5 112.6 . . ? C5 C4 C3 121.6(2) . . ? C5 C4 H4 107.0 . . ? C5 C6 C7 133.2(2) . . ? C5 C6 H6 113.4 . . ? C6 C5 C4 134.9(2) . . ? C6 C5 H5 112.6 . . ? C6 C7 H7 115.7 . . ? C7 C6 H6 113.4 . . ? C7 C8 C1 126.2(2) . . ? C7 C8 H8 116.9 . . ? C8 C1 C2 111.2(2) . . ? C8 C1 C9 111.5(2) . . ? C8 C1 H1 108.0 . . ? C8 C7 C6 128.5(2) . . ? C8 C7 H7 115.7 . . ? C9 O1 H1O 108(3) . . ? C9 C1 C2 109.96(19) . . ? C9 C1 H1 108.0 . . ? C10 O2 C2 109.44(19) . . ? C10 O3 C3 106.09(19) . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? C10 C12 H12A 109.5 . . ? C10 C12 H12B 109.5 . . ? C10 C12 H12C 109.5 . . ? C12 C10 C11 113.1(3) . . ? H9A C9 H9B 108.3 . . ? H11A C11 H11B 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? H12A C12 H12B 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? 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 O3 C3 C2 O2 -20.4(2) . . . . ? O3 C3 C2 C1 100.2(2) . . . . ? O3 C3 C4 O4 76.5(3) . . . . ? O3 C3 C4 C5 -47.0(3) . . . . ? O4 C4 C5 C6 -144.2(3) . . . . ? C1 C8 C7 C6 3.9(5) . . . . ? C2 O2 C10 O3 21.7(3) . . . . ? C2 O2 C10 C11 -98.1(3) . . . . ? C2 O2 C10 C12 137.4(2) . . . . ? C2 C1 C9 O1 -65.3(3) . . . . ? C2 C3 C4 O4 -162.6(2) . . . . ? C2 C3 C4 C5 74.0(3) . . . . ? C3 O3 C10 O2 -35.4(3) . . . . ? C3 O3 C10 C11 82.8(3) . . . . ? C3 O3 C10 C12 -152.3(2) . . . . ? C3 C4 C5 C6 -22.6(5) . . . . ? C4 C3 C2 O2 -145.3(2) . . . . ? C4 C3 C2 C1 -24.6(3) . . . . ? C5 C6 C7 C8 -30.4(6) . . . . ? C7 C6 C5 C4 -3.8(6) . . . . ? C7 C8 C1 C2 82.8(3) . . . . ? C7 C8 C1 C9 -154.1(3) . . . . ? C8 C1 C2 O2 41.9(3) . . . . ? C8 C1 C2 C3 -75.3(3) . . . . ? C8 C1 C9 O1 170.9(2) . . . . ? C9 C1 C2 O2 -82.0(3) . . . . ? C9 C1 C2 C3 160.8(2) . . . . ? C10 O3 C3 C2 34.5(2) . . . . ? C10 O3 C3 C4 164.3(2) . . . . ? C10 O2 C2 C1 -126.1(2) . . . . ? C10 O2 C2 C3 -0.7(3) . . . . ? #===END #=============================================================================== data_diol_2 _database_code_depnum_ccdc_archive 'CCDC 658131' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; (3aS*,4S*,9S*,9aR*)-9-(hydroxymethyl)-2,2-dimethyl-3a,4,7,8,9,9a-hexahydro- cycloocta[d][1,3]dioxol-4-ol ; _chemical_name_common ; (3aS*,4S*,9S*,9aR*)-9-(hydroxymethyl)-2,2-dimethyl- 3a,4,7,8,9,9a-hexahydro-cycloocta(d)(1,3)dioxol-4-ol ; _chemical_melting_point ? _chemical_formula_moiety 'C12 H20 O4' _chemical_formula_structural 'C12 H20 O4' _chemical_formula_sum 'C12 H20 O4' _chemical_formula_iupac 'C12 H20 O4' _chemical_formula_weight 228.28 _chemical_compound_source 'see text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0106 0.0060 '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 0.0033 0.0016 '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 2yn' _symmetry_space_group_name_H-M 'P 21/n' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 1/2-x,1/2+y,1/2-z 3 -x,-y,-z 4 1/2+x,1/2-y,1/2+z _cell_length_a 8.8996(16) _cell_length_b 14.342(3) _cell_length_c 19.650(4) _cell_angle_alpha 90.00 _cell_angle_beta 102.262(3) _cell_angle_gamma 90.00 _cell_volume 2450.8(8) _cell_formula_units_Z 8 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _cell_special_details ; ; _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.10 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.242 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 992 _exptl_absorpt_coefficient_mu 0.092 _exptl_crystal_density_meas_temp ? _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1997)' _exptl_absorpt_correction_T_min 0.9297 _exptl_absorpt_correction_T_max 0.9909 #=============================================================================== # 7. EXPERIMENTAL DATA _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoKa _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? _diffrn_reflns_number 23797 _diffrn_reflns_av_R_equivalents 0.0455 _diffrn_reflns_av_sigmaI/netI 0.0341 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.77 _diffrn_reflns_theta_max 25.35 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.998 _diffrn_reflns_reduction_process ; ; _reflns_number_total 4481 _reflns_number_gt 3276 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement 'SMART (Bruker, 1998)' _computing_data_reduction 'SAINT (Bruker, 1998)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993)' _computing_publication_material 'PLATON (Spek, 2003)' #=============================================================================== # 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 _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0381P)^2^+0.7301P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4481 _refine_ls_number_parameters 297 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0775 _refine_ls_R_factor_gt 0.0514 _refine_ls_wR_factor_ref 0.1101 _refine_ls_wR_factor_gt 0.1025 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.070 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.165 _refine_diff_density_min -0.132 _refine_diff_density_rms 0.033 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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 0.03868(16) -0.01112(11) 0.25540(8) 0.0511(4) Uani 1 1 d . . . O2 O -0.17089(14) 0.12675(10) 0.17875(7) 0.0441(4) Uani 1 1 d . . . O3 O -0.08771(14) 0.21032(10) 0.09573(7) 0.0435(4) Uani 1 1 d . . . O4 O 0.19535(16) 0.39500(11) 0.19075(9) 0.0587(5) Uani 1 1 d . . . O5 O 0.95262(18) 0.47964(11) 0.23594(9) 0.0599(5) Uani 1 1 d . . . O6 O 1.10180(14) 0.62790(9) 0.17446(7) 0.0406(3) Uani 1 1 d . . . O7 O 0.94946(14) 0.72620(10) 0.09878(7) 0.0395(3) Uani 1 1 d . . . O8 O 0.75955(17) 0.89428(11) 0.20623(9) 0.0571(4) Uani 1 1 d . . . C1 C 0.0777(2) 0.05004(14) 0.20336(10) 0.0385(5) Uani 1 1 d . . . C2 C -0.0093(2) 0.14100(13) 0.20346(10) 0.0359(5) Uani 1 1 d . . . C3 C 0.0252(2) 0.22231(14) 0.15897(10) 0.0363(5) Uani 1 1 d . . . C4 C 0.1859(2) 0.23638(14) 0.14382(10) 0.0371(5) Uani 1 1 d . . . C5 C 0.2246(2) 0.18235(16) 0.08232(11) 0.0469(6) Uani 1 1 d . . . C6 C 0.2695(2) 0.07955(16) 0.09371(12) 0.0513(6) Uani 1 1 d . . . C7 C 0.1362(2) 0.01426(15) 0.08768(12) 0.0486(6) Uani 1 1 d . . . C8 C 0.0530(2) 0.00267(14) 0.13472(11) 0.0438(5) Uani 1 1 d . . . C9 C 0.2098(3) 0.34006(15) 0.13199(12) 0.0498(6) Uani 1 1 d . . . C10 C -0.2230(2) 0.17858(15) 0.11562(11) 0.0409(5) Uani 1 1 d . . . C11 C -0.3074(3) 0.11386(18) 0.06013(13) 0.0620(7) Uani 1 1 d . . . C12 C -0.3217(3) 0.25899(17) 0.13043(14) 0.0606(7) Uani 1 1 d . . . C13 C 0.8711(2) 0.54857(14) 0.18899(11) 0.0421(5) Uani 1 1 d . . . C14 C 0.9622(2) 0.63868(13) 0.19881(10) 0.0346(5) Uani 1 1 d . . . C15 C 0.8924(2) 0.72706(13) 0.16122(10) 0.0324(4) Uani 1 1 d . . . C16 C 0.7180(2) 0.74449(13) 0.14565(10) 0.0349(5) Uani 1 1 d . . . C17 C 0.6232(2) 0.70158(15) 0.07899(11) 0.0470(5) Uani 1 1 d . . . C18 C 0.5861(2) 0.59783(16) 0.07938(13) 0.0563(6) Uani 1 1 d . . . C19 C 0.7149(3) 0.53531(17) 0.06846(14) 0.0599(7) Uani 1 1 d . . . C20 C 0.8373(3) 0.51382(15) 0.11594(13) 0.0515(6) Uani 1 1 d . . . C21 C 0.6884(2) 0.84929(14) 0.14339(12) 0.0478(6) Uani 1 1 d . . . C22 C 1.1009(2) 0.68934(14) 0.11654(10) 0.0377(5) Uani 1 1 d . . . C23 C 1.1312(3) 0.63394(18) 0.05550(12) 0.0595(7) Uani 1 1 d . . . C24 C 1.2186(2) 0.76497(16) 0.13877(13) 0.0550(6) Uani 1 1 d . . . H1O H -0.0454 -0.0351 0.2401 0.077 Uiso 1 1 calc R . . H4O H 0.2787 0.4185 0.2080 0.088 Uiso 1 1 calc R . . H5O H 1.0256 0.4600 0.2208 0.090 Uiso 1 1 calc R . . H8O H 0.6936 0.9191 0.2236 0.086 Uiso 1 1 calc R . . H1 H 0.1876 0.0642 0.2176 0.046 Uiso 1 1 calc R . . H2 H 0.0069 0.1628 0.2517 0.043 Uiso 1 1 calc R . . H3 H -0.0010 0.2797 0.1809 0.044 Uiso 1 1 calc R . . H4 H 0.2610 0.2179 0.1857 0.045 Uiso 1 1 calc R . . H5A H 0.1360 0.1858 0.0439 0.056 Uiso 1 1 calc R . . H5B H 0.3084 0.2145 0.0678 0.056 Uiso 1 1 calc R . . H6A H 0.3293 0.0616 0.0599 0.062 Uiso 1 1 calc R . . H6B H 0.3350 0.0727 0.1397 0.062 Uiso 1 1 calc R . . H7 H 0.1102 -0.0211 0.0472 0.058 Uiso 1 1 calc R . . H8 H -0.0288 -0.0389 0.1241 0.053 Uiso 1 1 calc R . . H9A H 0.3113 0.3494 0.1224 0.060 Uiso 1 1 calc R . . H9B H 0.1347 0.3608 0.0916 0.060 Uiso 1 1 calc R . . H11A H -0.3447 0.1484 0.0181 0.093 Uiso 1 1 calc R . . H11B H -0.3926 0.0861 0.0755 0.093 Uiso 1 1 calc R . . H11C H -0.2388 0.0658 0.0514 0.093 Uiso 1 1 calc R . . H12A H -0.2623 0.2984 0.1656 0.091 Uiso 1 1 calc R . . H12B H -0.4089 0.2351 0.1464 0.091 Uiso 1 1 calc R . . H12C H -0.3564 0.2944 0.0886 0.091 Uiso 1 1 calc R . . H13 H 0.7726 0.5602 0.2022 0.051 Uiso 1 1 calc R . . H14 H 0.9894 0.6522 0.2488 0.042 Uiso 1 1 calc R . . H15 H 0.9407 0.7801 0.1889 0.039 Uiso 1 1 calc R . . H16 H 0.6786 0.7192 0.1848 0.042 Uiso 1 1 calc R . . H17B H 0.5267 0.7353 0.0671 0.056 Uiso 1 1 calc R . . H17A H 0.6776 0.7126 0.0419 0.056 Uiso 1 1 calc R . . H18B H 0.5605 0.5823 0.1236 0.068 Uiso 1 1 calc R . . H18A H 0.4960 0.5855 0.0431 0.068 Uiso 1 1 calc R . . H19 H 0.7069 0.5098 0.0243 0.072 Uiso 1 1 calc R . . H20 H 0.9085 0.4738 0.1030 0.062 Uiso 1 1 calc R . . H21A H 0.7269 0.8762 0.1051 0.057 Uiso 1 1 calc R . . H21B H 0.5784 0.8603 0.1346 0.057 Uiso 1 1 calc R . . H23A H 1.0511 0.5886 0.0417 0.089 Uiso 1 1 calc R . . H23B H 1.2285 0.6028 0.0687 0.089 Uiso 1 1 calc R . . H23C H 1.1331 0.6752 0.0172 0.089 Uiso 1 1 calc R . . H24A H 1.2174 0.8069 0.1006 0.083 Uiso 1 1 calc R . . H24B H 1.3188 0.7375 0.1526 0.083 Uiso 1 1 calc R . . H24C H 1.1945 0.7987 0.1773 0.083 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0414(9) 0.0533(10) 0.0569(10) 0.0207(8) 0.0065(7) -0.0007(7) O2 0.0310(7) 0.0483(9) 0.0546(9) 0.0107(7) 0.0128(6) -0.0016(6) O3 0.0296(7) 0.0558(9) 0.0441(8) 0.0123(7) 0.0058(6) -0.0022(6) O4 0.0407(9) 0.0411(9) 0.0937(13) -0.0135(9) 0.0127(9) -0.0066(7) O5 0.0514(10) 0.0480(10) 0.0880(12) 0.0300(9) 0.0322(9) 0.0116(8) O6 0.0327(7) 0.0393(8) 0.0513(9) 0.0102(7) 0.0126(6) 0.0060(6) O7 0.0308(7) 0.0499(9) 0.0401(8) 0.0107(7) 0.0128(6) 0.0084(6) O8 0.0466(9) 0.0437(9) 0.0862(12) -0.0219(8) 0.0258(8) -0.0004(7) C1 0.0323(11) 0.0404(12) 0.0423(12) 0.0055(10) 0.0067(9) -0.0005(9) C2 0.0344(11) 0.0397(12) 0.0337(11) -0.0022(9) 0.0078(9) -0.0041(9) C3 0.0335(10) 0.0343(11) 0.0410(12) -0.0022(9) 0.0074(9) -0.0017(9) C4 0.0306(10) 0.0386(12) 0.0415(12) 0.0024(9) 0.0058(9) -0.0039(9) C5 0.0394(12) 0.0587(15) 0.0450(13) 0.0010(11) 0.0143(10) -0.0064(10) C6 0.0411(12) 0.0612(15) 0.0557(14) -0.0116(12) 0.0194(11) 0.0035(11) C7 0.0467(13) 0.0467(14) 0.0519(14) -0.0159(11) 0.0092(11) 0.0023(10) C8 0.0370(11) 0.0342(12) 0.0591(14) -0.0041(10) 0.0080(10) -0.0005(9) C9 0.0416(13) 0.0428(13) 0.0648(15) 0.0059(12) 0.0104(11) -0.0078(10) C10 0.0291(11) 0.0457(13) 0.0479(13) 0.0095(10) 0.0083(9) 0.0020(9) C11 0.0401(13) 0.0780(18) 0.0645(16) -0.0086(14) 0.0037(12) -0.0073(12) C12 0.0450(13) 0.0559(16) 0.0806(18) 0.0073(13) 0.0127(13) 0.0126(11) C13 0.0368(11) 0.0353(12) 0.0580(14) 0.0087(10) 0.0183(10) 0.0052(9) C14 0.0357(11) 0.0348(11) 0.0341(11) -0.0009(9) 0.0092(9) 0.0018(9) C15 0.0328(10) 0.0305(11) 0.0354(11) -0.0013(9) 0.0107(9) -0.0001(8) C16 0.0309(10) 0.0345(11) 0.0422(12) 0.0006(9) 0.0145(9) 0.0005(8) C17 0.0322(11) 0.0589(15) 0.0485(13) -0.0027(11) 0.0050(10) 0.0044(10) C18 0.0389(12) 0.0589(16) 0.0665(16) -0.0188(13) 0.0006(11) -0.0091(11) C19 0.0532(15) 0.0538(15) 0.0723(17) -0.0312(13) 0.0124(13) -0.0103(12) C20 0.0463(14) 0.0327(12) 0.0772(17) -0.0144(11) 0.0170(13) -0.0056(10) C21 0.0376(12) 0.0396(13) 0.0683(16) 0.0007(11) 0.0159(11) 0.0070(10) C22 0.0306(10) 0.0405(12) 0.0432(12) 0.0068(10) 0.0106(9) 0.0058(9) C23 0.0502(14) 0.0755(18) 0.0583(15) -0.0060(13) 0.0240(12) 0.0086(12) C24 0.0412(12) 0.0528(15) 0.0730(17) 0.0097(12) 0.0163(12) -0.0021(11) #=============================================================================== # 10. MOLECULAR GEOMETRY _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 C1 1.444(2) . ? O1 H1O 0.8200 . ? O2 C2 1.431(2) . ? O2 C10 1.436(2) . ? O3 C10 1.418(2) . ? O3 C3 1.433(2) . ? O4 C9 1.426(3) . ? O4 H4O 0.8200 . ? O5 C13 1.439(2) . ? O5 H5O 0.8200 . ? O6 C14 1.432(2) . ? O6 C22 1.438(2) . ? O7 C22 1.421(2) . ? O7 C15 1.424(2) . ? O8 C21 1.418(3) . ? O8 H8O 0.8200 . ? C1 C8 1.484(3) . ? C1 C2 1.517(3) . ? C1 H1 0.9800 . ? C2 C3 1.527(3) . ? C2 H2 0.9800 . ? C3 C4 1.535(3) . ? C3 H3 0.9800 . ? C4 C9 1.527(3) . ? C4 C5 1.535(3) . ? C4 H4 0.9800 . ? C5 C6 1.532(3) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.496(3) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.312(3) . ? C7 H7 0.9300 . ? C8 H8 0.9300 . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.505(3) . ? C10 C12 1.515(3) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 C20 1.489(3) . ? C13 C14 1.516(3) . ? C13 H13 0.9800 . ? C14 C15 1.531(3) . ? C14 H14 0.9800 . ? C15 C16 1.537(2) . ? C15 H15 0.9800 . ? C16 C21 1.525(3) . ? C16 C17 1.529(3) . ? C16 H16 0.9800 . ? C17 C18 1.525(3) . ? C17 H17B 0.9700 . ? C17 H17A 0.9700 . ? C18 C19 1.506(3) . ? C18 H18B 0.9700 . ? C18 H18A 0.9700 . ? C19 C20 1.312(3) . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 C24 1.506(3) . ? C22 C23 1.510(3) . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? 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 108.76(16) . . ? O1 C1 C8 110.72(17) . . ? O1 C1 H1 107.5 . . ? O2 C2 C1 110.68(16) . . ? O2 C2 C3 102.99(15) . . ? O2 C2 H2 107.7 . . ? O2 C10 C11 109.06(18) . . ? O2 C10 C12 108.80(17) . . ? O3 C3 C2 102.43(15) . . ? O3 C3 C4 111.01(15) . . ? O3 C3 H3 107.1 . . ? O3 C10 O2 105.47(14) . . ? O3 C10 C11 108.70(17) . . ? O3 C10 C12 111.68(18) . . ? O4 C9 C4 112.06(18) . . ? O4 C9 H9A 109.2 . . ? O4 C9 H9B 109.2 . . ? O5 C13 C14 108.71(16) . . ? O5 C13 C20 111.05(18) . . ? O5 C13 H13 107.7 . . ? O6 C14 C13 110.12(15) . . ? O6 C14 C15 102.71(14) . . ? O6 C14 H14 108.0 . . ? O6 C22 C23 109.54(17) . . ? O6 C22 C24 108.97(16) . . ? O7 C15 C14 103.08(14) . . ? O7 C15 C16 111.08(15) . . ? O7 C15 H15 106.9 . . ? O7 C22 O6 105.54(14) . . ? O7 C22 C23 108.69(17) . . ? O7 C22 C24 111.60(17) . . ? O8 C21 C16 112.38(18) . . ? O8 C21 H21A 109.1 . . ? O8 C21 H21B 109.1 . . ? C1 O1 H1O 109.5 . . ? C1 C2 C3 119.39(16) . . ? C1 C2 H2 107.7 . . ? C1 C8 H8 117.1 . . ? C2 O2 C10 109.64(14) . . ? C2 C1 H1 107.5 . . ? C2 C3 C4 121.37(16) . . ? C2 C3 H3 107.1 . . ? C3 C2 H2 107.7 . . ? C3 C4 C5 117.40(17) . . ? C3 C4 H4 107.4 . . ? C4 C3 H3 107.1 . . ? C4 C5 H5A 107.9 . . ? C4 C5 H5B 107.9 . . ? C4 C9 H9A 109.2 . . ? C4 C9 H9B 109.2 . . ? C5 C4 H4 107.4 . . ? C5 C6 H6A 108.7 . . ? C5 C6 H6B 108.7 . . ? C6 C5 C4 117.79(18) . . ? C6 C5 H5A 107.9 . . ? C6 C5 H5B 107.9 . . ? C6 C7 H7 117.3 . . ? C7 C6 C5 114.37(18) . . ? C7 C6 H6A 108.7 . . ? C7 C6 H6B 108.7 . . ? C7 C8 C1 125.8(2) . . ? C7 C8 H8 117.1 . . ? C8 C1 C2 114.67(17) . . ? C8 C1 H1 107.5 . . ? C8 C7 C6 125.5(2) . . ? C8 C7 H7 117.3 . . ? C9 O4 H4O 109.5 . . ? C9 C4 C3 108.86(17) . . ? C9 C4 C5 108.07(17) . . ? C9 C4 H4 107.4 . . ? C10 O3 C3 106.26(14) . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? C10 C12 H12A 109.5 . . ? C10 C12 H12B 109.5 . . ? C10 C12 H12C 109.5 . . ? C11 C10 C12 112.85(18) . . ? C13 O5 H5O 109.5 . . ? C13 C14 C15 119.56(16) . . ? C13 C14 H14 108.0 . . ? C13 C20 H20 117.5 . . ? C14 O6 C22 109.82(13) . . ? C14 C13 H13 107.7 . . ? C14 C15 C16 121.31(15) . . ? C14 C15 H15 106.8 . . ? C15 C14 H14 108.0 . . ? C15 C16 H16 107.4 . . ? C16 C15 H15 106.8 . . ? C16 C17 H17A 107.8 . . ? C16 C17 H17B 107.8 . . ? C16 C21 H21A 109.1 . . ? C16 C21 H21B 109.1 . . ? C17 C16 C15 117.08(16) . . ? C17 C16 H16 107.4 . . ? C17 C18 H18A 108.7 . . ? C17 C18 H18B 108.7 . . ? C18 C17 C16 118.00(18) . . ? C18 C17 H17B 107.8 . . ? C18 C17 H17A 107.8 . . ? C18 C19 H19 117.2 . . ? C19 C18 C17 114.07(19) . . ? C19 C18 H18A 108.7 . . ? C19 C18 H18B 108.7 . . ? C19 C20 C13 125.0(2) . . ? C19 C20 H20 117.5 . . ? C20 C13 C14 113.65(17) . . ? C20 C13 H13 107.7 . . ? C20 C19 C18 125.5(2) . . ? C20 C19 H19 117.2 . . ? C21 O8 H8O 109.5 . . ? C21 C16 C15 109.10(16) . . ? C21 C16 C17 108.13(17) . . ? C21 C16 H16 107.4 . . ? C22 O7 C15 106.55(14) . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? C22 C24 H24A 109.5 . . ? C22 C24 H24B 109.5 . . ? C22 C24 H24C 109.5 . . ? C24 C22 C23 112.27(18) . . ? H5A C5 H5B 107.2 . . ? H6A C6 H6B 107.6 . . ? H9A C9 H9B 107.9 . . ? H11A C11 H11B 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? H12A C12 H12B 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? H17B C17 H17A 107.1 . . ? H18B C18 H18A 107.6 . . ? H21A C21 H21B 107.9 . . ? H23A C23 H23B 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? H24A C24 H24B 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? 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 -67.7(2) . . . . ? O1 C1 C2 C3 173.02(16) . . . . ? O1 C1 C8 C7 -145.5(2) . . . . ? O2 C2 C3 O3 -29.43(18) . . . . ? O2 C2 C3 C4 -153.79(17) . . . . ? O3 C3 C4 C5 -35.5(2) . . . . ? O3 C3 C4 C9 87.6(2) . . . . ? O5 C13 C14 O6 68.5(2) . . . . ? O5 C13 C14 C15 -172.98(16) . . . . ? O5 C13 C20 C19 147.0(2) . . . . ? O6 C14 C15 O7 28.84(18) . . . . ? O6 C14 C15 C16 153.83(16) . . . . ? O7 C15 C16 C17 36.0(2) . . . . ? O7 C15 C16 C21 -87.20(19) . . . . ? C1 C2 C3 O3 93.66(19) . . . . ? C1 C2 C3 C4 -30.7(3) . . . . ? C2 C1 C8 C7 91.0(3) . . . . ? C2 C3 C4 C5 84.8(2) . . . . ? C2 C3 C4 C9 -152.07(18) . . . . ? C2 O2 C10 O3 10.3(2) . . . . ? C2 O2 C10 C11 126.90(17) . . . . ? C2 O2 C10 C12 -109.62(18) . . . . ? C3 O3 C10 O2 -30.14(19) . . . . ? C3 O3 C10 C11 -146.97(17) . . . . ? C3 O3 C10 C12 87.9(2) . . . . ? C3 C4 C5 C6 -79.4(2) . . . . ? C3 C4 C9 O4 58.8(2) . . . . ? C4 C5 C6 C7 81.4(2) . . . . ? C5 C4 C9 O4 -172.62(16) . . . . ? C5 C6 C7 C8 -75.7(3) . . . . ? C6 C7 C8 C1 -1.8(4) . . . . ? C8 C1 C2 O2 56.8(2) . . . . ? C8 C1 C2 C3 -62.4(2) . . . . ? C9 C4 C5 C6 157.07(18) . . . . ? C10 O2 C2 C1 -116.75(17) . . . . ? C10 O2 C2 C3 11.97(19) . . . . ? C10 O3 C3 C2 36.95(18) . . . . ? C10 O3 C3 C4 167.93(16) . . . . ? C13 C14 C15 O7 -93.39(19) . . . . ? C13 C14 C15 C16 31.6(3) . . . . ? C14 O6 C22 O7 -9.3(2) . . . . ? C14 O6 C22 C23 -126.12(17) . . . . ? C14 O6 C22 C24 110.69(17) . . . . ? C14 C13 C20 C19 -90.1(3) . . . . ? C14 C15 C16 C17 -85.3(2) . . . . ? C14 C15 C16 C21 151.59(18) . . . . ? C15 O7 C22 O6 28.73(19) . . . . ? C15 O7 C22 C23 146.15(17) . . . . ? C15 O7 C22 C24 -89.51(19) . . . . ? C15 C16 C17 C18 78.1(2) . . . . ? C15 C16 C21 O8 -57.5(2) . . . . ? C16 C17 C18 C19 -80.9(3) . . . . ? C17 C16 C21 O8 174.13(16) . . . . ? C17 C18 C19 C20 78.2(3) . . . . ? C18 C19 C20 C13 -0.7(4) . . . . ? C20 C13 C14 O6 -55.7(2) . . . . ? C20 C13 C14 C15 62.8(2) . . . . ? C21 C16 C17 C18 -158.28(18) . . . . ? C22 O6 C14 C13 116.34(17) . . . . ? C22 O6 C14 C15 -12.06(19) . . . . ? C22 O7 C15 C14 -35.76(18) . . . . ? C22 O7 C15 C16 -167.16(15) . . . . ? #===END