# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_coden_Cambridge 182 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'G. Mehta' 'Saikat Sen' _publ_contact_author_name 'G. Mehta' _publ_contact_author_email GM@ORGCHEM.IISC.ERNET.IN _publ_section_title ; Towards a temperature guided molecular switch: An unusual reversible low temperature polymorphic phase transition in a conformationally locked environment ; # Attachment 'CIF.cif' data_tetraacetate_alpha_form_RT _database_code_depnum_ccdc_archive 'CCDC 724609' #=============================================================================== _audit_creation_date 'Mar 02 19:52:37 2009' _audit_creation_method 'PLATON option' # 5. CHEMICAL DATA _chemical_name_systematic ; (all trans)-3,6,7-tri(acetyloxy)-4a,8a-dihydroxyperhydro-2-naphthalenyl acetate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H26 O10' _chemical_formula_structural 'C18 H26 O10' _chemical_formula_sum 'C18 H26 O10' _chemical_formula_iupac 'C18 H26 O10' _chemical_formula_weight 402.39 _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 2/c' _symmetry_Int_Tables_number 15 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,y,1/2-z 3 -x,-y,-z 4 x,-y,1/2+z 5 1/2+x,1/2+y,z 6 1/2-x,1/2+y,1/2-z 7 1/2-x,1/2-y,-z 8 1/2+x,1/2-y,1/2+z _cell_length_a 21.433(7) _cell_length_b 5.7126(18) _cell_length_c 16.720(5) _cell_angle_alpha 90 _cell_angle_beta 105.664(5) _cell_angle_gamma 90 _cell_volume 1971.1(11) _cell_formula_units_Z 4 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 698 _cell_measurement_theta_min 2.76 _cell_measurement_theta_max 23.43 _cell_special_details ; ; _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.24 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.356 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 856 _exptl_absorpt_coefficient_mu 0.111 _exptl_crystal_density_meas_temp ? _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1997)' _exptl_absorpt_correction_T_min 0.9439 _exptl_absorpt_correction_T_max 0.9738 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_ambient_temperature 291(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 0 _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 6929 _diffrn_reflns_av_R_equivalents 0.0176 _diffrn_reflns_av_sigmaI/netI 0.0162 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.53 _diffrn_reflns_theta_max 25.35 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _diffrn_reflns_reduction_process ; ; _reflns_number_total 1800 _reflns_number_gt 1419 _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. The carbonyl oxygen atom O5 is diordered over two sites A and B, with occupancies 0.52 and 0.48 respectively. ; _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^)+(0.0753P)^2^+1.3499P] 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 1800 _refine_ls_number_parameters 139 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0642 _refine_ls_R_factor_gt 0.0514 _refine_ls_wR_factor_ref 0.1518 _refine_ls_wR_factor_gt 0.1402 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.213 _refine_diff_density_min -0.182 _refine_diff_density_rms 0.041 #=============================================================================== # 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 0.59427(7) 0.2114(3) 0.38645(8) 0.0575(4) Uani 1 1 d . . . O2 O 0.47146(7) 0.2187(2) 0.41996(8) 0.0524(4) Uani 1 1 d . . . O3 O 0.34652(7) 0.1654(3) 0.43824(10) 0.0690(5) Uani 1 1 d . A . O4 O 0.59879(11) 0.0372(3) 0.26928(11) 0.0888(6) Uani 1 1 d . . . O5A O 0.2592(7) -0.0147(16) 0.3678(12) 0.144(8) Uani 0.52(3) 1 d P A 1 O5B O 0.2473(3) 0.051(2) 0.4283(15) 0.125(6) Uani 0.48(3) 1 d P A 2 C1 C 0.59745(10) -0.0126(4) 0.42889(13) 0.0535(5) Uani 1 1 d . . . C2 C 0.53162(10) -0.1314(4) 0.41179(12) 0.0508(5) Uani 1 1 d . . . C3 C 0.48438(9) -0.0135(3) 0.45299(11) 0.0447(5) Uani 1 1 d . . . C4 C 0.42154(10) -0.1537(4) 0.43847(12) 0.0515(5) Uani 1 1 d . . . C5 C 0.37290(10) -0.0502(4) 0.48012(13) 0.0554(6) Uani 1 1 d . . . C6 C 0.59617(10) 0.2130(4) 0.30748(13) 0.0556(6) Uani 1 1 d . . . C7 C 0.59517(13) 0.4542(4) 0.27488(15) 0.0713(7) Uani 1 1 d . . . C8 C 0.28552(14) 0.1754(7) 0.3978(2) 0.0992(11) Uani 1 1 d . . . C9 C 0.26633(14) 0.4011(7) 0.3563(2) 0.1094(12) Uani 1 1 d . A . H2O H 0.4429 0.2138 0.3760 0.079 Uiso 1 1 calc R . . H1 H 0.6273 -0.1159 0.4104 0.064 Uiso 1 1 calc R . . H2A H 0.5380 -0.2922 0.4309 0.061 Uiso 1 1 calc R . . H2B H 0.5123 -0.1348 0.3522 0.061 Uiso 1 1 calc R . . H4A H 0.4015 -0.1637 0.3792 0.062 Uiso 1 1 calc R . . H4B H 0.4320 -0.3117 0.4590 0.062 Uiso 1 1 calc R . . H5 H 0.3376 -0.1623 0.4761 0.066 Uiso 1 1 calc R . . H7A H 0.5930 0.5639 0.3175 0.107 Uiso 1 1 calc R . . H7B H 0.5580 0.4735 0.2281 0.107 Uiso 1 1 calc R . . H7C H 0.6339 0.4815 0.2578 0.107 Uiso 1 1 calc R . . H9A H 0.3017 0.4635 0.3378 0.164 Uiso 1 1 calc R . . H9B H 0.2553 0.5085 0.3945 0.164 Uiso 1 1 calc R . . H9C H 0.2295 0.3788 0.3093 0.164 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 0.0684(9) 0.0643(10) 0.0449(8) -0.0027(7) 0.0241(7) -0.0019(7) O2 0.0562(9) 0.0565(9) 0.0398(7) 0.0072(6) 0.0048(6) 0.0042(7) O3 0.0460(9) 0.0798(11) 0.0741(11) 0.0112(9) 0.0043(7) 0.0069(8) O4 0.1317(17) 0.0858(13) 0.0556(10) -0.0171(10) 0.0367(11) -0.0085(12) O5A 0.096(7) 0.115(5) 0.164(11) 0.034(5) -0.065(7) -0.027(4) O5B 0.050(3) 0.138(6) 0.182(14) 0.051(7) 0.021(4) -0.002(3) C1 0.0549(12) 0.0599(13) 0.0473(11) -0.0015(10) 0.0167(9) 0.0038(10) C2 0.0575(12) 0.0553(12) 0.0387(10) -0.0034(9) 0.0114(9) 0.0015(10) C3 0.0483(10) 0.0478(11) 0.0360(10) 0.0024(8) 0.0078(8) 0.0034(9) C4 0.0537(12) 0.0591(13) 0.0377(10) -0.0031(9) 0.0052(8) -0.0023(10) C5 0.0479(11) 0.0648(14) 0.0505(12) 0.0034(10) 0.0083(9) -0.0007(10) C6 0.0516(12) 0.0745(15) 0.0402(10) -0.0089(11) 0.0117(9) -0.0069(11) C7 0.0829(17) 0.0786(17) 0.0539(13) 0.0019(12) 0.0211(12) -0.0130(14) C8 0.0509(15) 0.106(3) 0.121(3) 0.030(2) -0.0106(17) -0.0012(16) C9 0.0595(16) 0.122(3) 0.134(3) 0.042(2) 0.0035(17) 0.0165(17) #=============================================================================== # 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 1.456(3) . ? O1 C6 1.332(2) . ? O2 C3 1.434(2) . ? O2 H2O 0.8200 . ? O3 C5 1.454(3) . ? O3 C8 1.301(3) . ? O5A C8 1.264(9) . ? O5B C8 1.286(7) . ? C1 H1 0.9800 . ? C2 C1 1.521(3) . ? C2 C3 1.527(3) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C4 C3 1.529(3) . ? C4 C5 1.521(3) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 H5 0.9800 . ? C6 O4 1.200(3) . ? C6 C7 1.479(3) . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 C9 1.470(5) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 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 112.42(17) . . ? O1 C6 C7 111.75(19) . . ? O1 C1 H1 108.9 . . ? O2 C3 C2 108.46(16) . . ? O2 C3 C4 110.67(15) . . ? O3 C5 C4 109.53(18) . . ? O3 C5 H5 109.1 . . ? O3 C8 C9 113.4(3) . . ? O4 C6 O1 122.7(2) . . ? O4 C6 C7 125.6(2) . . ? O5A C8 O5B 54.6(5) . . ? O5A C8 O3 116.5(7) . . ? O5A C8 C9 121.9(4) . . ? O5B C8 O3 115.3(7) . . ? O5B C8 C9 122.9(4) . . ? C1 C2 C3 114.38(18) . . ? C1 C2 H2A 108.7 . . ? C1 C2 H2B 108.7 . . ? C2 C3 C4 111.12(17) . . ? C2 C1 H1 108.9 . . ? C3 O2 H2O 109.5 . . ? C3 C2 H2A 108.7 . . ? C3 C2 H2B 108.7 . . ? C3 C4 H4A 108.7 . . ? C3 C4 H4B 108.7 . . ? C4 C5 H5 109.1 . . ? C5 C4 C3 114.01(17) . . ? C5 C4 H4A 108.7 . . ? C5 C4 H4B 108.7 . . ? C6 O1 C1 118.64(17) . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? C8 O3 C5 119.5(2) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H2A C2 H2B 107.6 . . ? H4A C4 H4B 107.6 . . ? H7A C7 H7B 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? H9A C9 H9B 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 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 C1 O1 C6 O4 1.9(3) . . . . ? C1 O1 C6 C7 -177.67(19) . . . . ? C1 C2 C3 O2 62.6(2) . . . . ? C1 C2 C3 C4 -175.55(16) . . . . ? C3 C2 C1 O1 -71.0(2) . . . . ? C3 C4 C5 O3 70.2(2) . . . . ? C5 O3 C8 O5A -28.6(14) . . . . ? C5 O3 C8 O5B 32.7(12) . . . . ? C5 O3 C8 C9 -177.9(3) . . . . ? C5 C4 C3 O2 -61.2(2) . . . . ? C5 C4 C3 C2 178.21(16) . . . . ? C6 O1 C1 C2 -83.6(2) . . . . ? C8 O3 C5 C4 113.8(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # # Hydrogen bonding scheme # ======== ======= ====== # # D H A D - H H...A D...A D - H...A symm(A) # - - - ----- ----- ----- --------- ------- O2 H2O O4 0.8200 2.5600 3.283(2) 148.00 2_655 yes #===END #=============================================================================== data_tetraacetate_beta_form_RT _database_code_depnum_ccdc_archive 'CCDC 724610' #=============================================================================== _audit_creation_date 'Mar 02 19:52:37 2009' _audit_creation_method 'PLATON
option' # 5. CHEMICAL DATA _chemical_name_systematic ; (all trans)-3,6,7-tri(acetyloxy)-4a,8a-dihydroxyperhydro-2-naphthalenyl acetate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H26 O10' _chemical_formula_structural 'C18 H26 O10' _chemical_formula_sum 'C18 H26 O10' _chemical_formula_iupac 'C18 H26 O10' _chemical_formula_weight 402.39 _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 2/c' _symmetry_Int_Tables_number 15 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,y,1/2-z 3 -x,-y,-z 4 x,-y,1/2+z 5 1/2+x,1/2+y,z 6 1/2-x,1/2+y,1/2-z 7 1/2-x,1/2-y,-z 8 1/2+x,1/2-y,1/2+z _cell_length_a 19.991(5) _cell_length_b 6.0024(15) _cell_length_c 16.225(4) _cell_angle_alpha 90 _cell_angle_beta 91.130(4) _cell_angle_gamma 90 _cell_volume 1946.6(8) _cell_formula_units_Z 4 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 815 _cell_measurement_theta_min 3.20 _cell_measurement_theta_max 23.69 _cell_special_details ; ; _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.12 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.373 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 856 _exptl_absorpt_coefficient_mu 0.113 _exptl_crystal_density_meas_temp ? _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1997)' _exptl_absorpt_correction_T_min 0.9467 _exptl_absorpt_correction_T_max 0.9866 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_ambient_temperature 291(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 0 _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 6976 _diffrn_reflns_av_R_equivalents 0.0170 _diffrn_reflns_av_sigmaI/netI 0.0151 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.04 _diffrn_reflns_theta_max 25.49 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.994 _diffrn_reflns_reduction_process ; ; _reflns_number_total 1807 _reflns_number_gt 1475 _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^)+(0.0574P)^2^+1.1118P] 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 1807 _refine_ls_number_parameters 130 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0505 _refine_ls_R_factor_gt 0.0405 _refine_ls_wR_factor_ref 0.1114 _refine_ls_wR_factor_gt 0.1061 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.049 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.275 _refine_diff_density_min -0.188 _refine_diff_density_rms 0.039 #=============================================================================== # 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 O2 O 0.03766(6) 1.17528(17) 1.07846(7) 0.0393(3) Uani 1 1 d . . . H2O H 0.0667 1.1457 1.1132 0.059 Uiso 1 1 calc R . . O3 O 0.09515(6) 0.73153(19) 0.85914(7) 0.0406(3) Uani 1 1 d . . . O1 O 0.16588(6) 1.0086(2) 1.03415(7) 0.0436(3) Uani 1 1 d . . . C2 C 0.06336(8) 0.7886(3) 1.04549(9) 0.0363(4) Uani 1 1 d . . . H2A H 0.0778 0.7617 1.1020 0.044 Uiso 1 1 calc R . . H2B H 0.0428 0.6526 1.0249 0.044 Uiso 1 1 calc R . . O5 O 0.11257(9) 0.9225(2) 0.74297(8) 0.0710(5) Uani 1 1 d . . . C3 C 0.01069(8) 0.9726(2) 1.04487(8) 0.0319(4) Uani 1 1 d . . . C1 C 0.12447(8) 0.8388(3) 0.99461(10) 0.0382(4) Uani 1 1 d . . . H1 H 0.1509 0.7022 0.9891 0.046 Uiso 1 1 calc R . . C4 C -0.05026(8) 0.9040(3) 1.09395(9) 0.0375(4) Uani 1 1 d . . . H4A H -0.0663 0.7620 1.0730 0.045 Uiso 1 1 calc R . . H4B H -0.0363 0.8820 1.1510 0.045 Uiso 1 1 calc R . . O4 O 0.22163(7) 0.7449(3) 1.10557(10) 0.0687(5) Uani 1 1 d . . . C5 C 0.10809(8) 0.9306(3) 0.90848(9) 0.0376(4) Uani 1 1 d . . . H5 H 0.1480 1.0047 0.8876 0.045 Uiso 1 1 calc R . . C8 C 0.10206(10) 0.7493(3) 0.77760(10) 0.0466(5) Uani 1 1 d . . . C6 C 0.21299(9) 0.9375(3) 1.08871(11) 0.0480(5) Uani 1 1 d . . . C9 C 0.09482(12) 0.5305(3) 0.73531(11) 0.0604(6) Uani 1 1 d . . . H9A H 0.0551 0.5316 0.7010 0.091 Uiso 1 1 calc R . . H9B H 0.0915 0.4144 0.7757 0.091 Uiso 1 1 calc R . . H9C H 0.1331 0.5044 0.7019 0.091 Uiso 1 1 calc R . . C7 C 0.25180(10) 1.1282(4) 1.12330(14) 0.0675(6) Uani 1 1 d . . . H7A H 0.2561 1.1121 1.1820 0.101 Uiso 1 1 calc R . . H7B H 0.2289 1.2648 1.1105 0.101 Uiso 1 1 calc R . . H7C H 0.2955 1.1307 1.0997 0.101 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 O2 0.0490(7) 0.0349(6) 0.0336(6) -0.0044(5) -0.0076(5) -0.0046(5) O3 0.0538(7) 0.0393(7) 0.0289(6) -0.0034(5) 0.0034(5) -0.0033(5) O1 0.0433(7) 0.0448(7) 0.0423(6) -0.0032(5) -0.0074(5) -0.0031(5) C2 0.0476(9) 0.0332(8) 0.0281(7) 0.0035(6) -0.0043(7) -0.0010(7) O5 0.1267(14) 0.0499(8) 0.0370(7) 0.0040(6) 0.0169(8) 0.0022(9) C3 0.0433(9) 0.0281(8) 0.0243(7) -0.0003(6) -0.0021(6) -0.0044(6) C1 0.0433(9) 0.0359(9) 0.0353(8) -0.0026(7) -0.0030(7) -0.0001(7) C4 0.0505(10) 0.0349(9) 0.0271(7) 0.0036(6) 0.0013(7) -0.0044(7) O4 0.0623(9) 0.0636(10) 0.0791(11) 0.0099(8) -0.0227(8) 0.0058(7) C5 0.0443(9) 0.0381(9) 0.0306(8) -0.0024(7) 0.0026(7) -0.0067(7) C8 0.0617(11) 0.0478(11) 0.0303(9) -0.0005(7) 0.0025(8) 0.0067(9) C6 0.0381(9) 0.0624(13) 0.0433(9) -0.0006(9) -0.0022(7) 0.0019(9) C9 0.0911(16) 0.0526(12) 0.0372(10) -0.0083(8) -0.0062(10) 0.0071(11) C7 0.0487(12) 0.0820(16) 0.0711(14) -0.0089(12) -0.0172(10) -0.0091(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 O2 C3 1.4337(18) . ? O2 H2O 0.8200 . ? O3 C8 1.337(2) . ? O3 C5 1.4586(19) . ? O1 C6 1.349(2) . ? O1 C1 1.455(2) . ? C2 C1 1.518(2) . ? C2 C3 1.526(2) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? O5 C8 1.202(2) . ? C3 C4 1.525(2) . ? C1 C5 1.532(2) . ? C1 H1 0.9800 . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? O4 C6 1.200(2) . ? C5 H5 0.9800 . ? C8 C9 1.487(3) . ? C6 C7 1.487(3) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 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 C3 O2 H2O 109.5 . . ? C8 O3 C5 117.19(13) . . ? C6 O1 C1 116.83(14) . . ? C1 C2 C3 114.53(13) . . ? C1 C2 H2A 108.6 . . ? C3 C2 H2A 108.6 . . ? C1 C2 H2B 108.6 . . ? C3 C2 H2B 108.6 . . ? H2A C2 H2B 107.6 . . ? O2 C3 C4 109.19(12) . . ? O2 C3 C2 110.94(12) . . ? C4 C3 C2 111.05(13) . . ? O1 C1 C2 110.88(13) . . ? O1 C1 C5 105.05(13) . . ? C2 C1 C5 114.07(13) . . ? O1 C1 H1 108.9 . . ? C2 C1 H1 108.9 . . ? C5 C1 H1 108.9 . . ? C3 C4 H4A 108.5 . . ? C3 C4 H4B 108.5 . . ? H4A C4 H4B 107.5 . . ? O3 C5 C1 103.78(13) . . ? O3 C5 H5 108.6 . . ? C1 C5 H5 108.6 . . ? O5 C8 O3 123.64(16) . . ? O5 C8 C9 124.34(16) . . ? O3 C8 C9 112.02(15) . . ? O4 C6 O1 123.39(18) . . ? O4 C6 C7 125.73(18) . . ? O1 C6 C7 110.88(17) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 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 C1 C2 C3 O2 -61.11(17) . . . . ? C1 C2 C3 C4 177.25(13) . . . . ? C6 O1 C1 C2 88.50(17) . . . . ? C6 O1 C1 C5 -147.82(14) . . . . ? C3 C2 C1 O1 71.78(17) . . . . ? C3 C2 C1 C5 -46.57(19) . . . . ? C8 O3 C5 C1 -157.51(15) . . . . ? O1 C1 C5 O3 154.67(12) . . . . ? C2 C1 C5 O3 -83.71(16) . . . . ? C5 O3 C8 O5 -6.5(3) . . . . ? C5 O3 C8 C9 173.78(15) . . . . ? C1 O1 C6 O4 -0.2(3) . . . . ? C1 O1 C6 C7 179.34(15) . . . . ? 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 # # Hydrogen bonding scheme # ======== ======= ====== # # D H A D - H H...A D...A D - H...A symm(A) # - - - ----- ----- ----- --------- ------- O2 H2O O5 0.8200 2.3200 3.091(2) 158.00 4_575 yes #===END #=============================================================================== data_tetraacetate_beta_form_100K _database_code_depnum_ccdc_archive 'CCDC 724611' #=============================================================================== _audit_creation_date 'Mar 02 19:52:37 2009' _audit_creation_method 'PLATON
option' # 5. CHEMICAL DATA _chemical_name_systematic ; (all trans)-3,6,7-tri(acetyloxy)-4a,8a-dihydroxyperhydro-2-naphthalenyl acetate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H26 O10' _chemical_formula_structural 'C18 H26 O10' _chemical_formula_sum 'C18 H26 O10' _chemical_formula_iupac 'C18 H26 O10' _chemical_formula_weight 402.39 _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 2/c' _symmetry_Int_Tables_number 15 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,y,1/2-z 3 -x,-y,-z 4 x,-y,1/2+z 5 1/2+x,1/2+y,z 6 1/2-x,1/2+y,1/2-z 7 1/2-x,1/2-y,-z 8 1/2+x,1/2-y,1/2+z _cell_length_a 19.430(4) _cell_length_b 6.0815(13) _cell_length_c 15.994(3) _cell_angle_alpha 90 _cell_angle_beta 91.849(4) _cell_angle_gamma 90 _cell_volume 1889.0(7) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 739 _cell_measurement_theta_min 2.55 _cell_measurement_theta_max 27.13 _cell_special_details ; ; _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.20 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.415 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 856 _exptl_absorpt_coefficient_mu 0.116 _exptl_crystal_density_meas_temp ? _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1997)' _exptl_absorpt_correction_T_min 0.9374 _exptl_absorpt_correction_T_max 0.9772 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_ambient_temperature 100(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 0 _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 7047 _diffrn_reflns_av_R_equivalents 0.0245 _diffrn_reflns_av_sigmaI/netI 0.0231 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.10 _diffrn_reflns_theta_max 25.99 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _diffrn_reflns_reduction_process ; ; _reflns_number_total 1853 _reflns_number_gt 1588 _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^)+(0.0396P)^2^+1.3854P] 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_number_reflns 1853 _refine_ls_number_parameters 179 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0431 _refine_ls_R_factor_gt 0.0343 _refine_ls_wR_factor_ref 0.0827 _refine_ls_wR_factor_gt 0.0795 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.376 _refine_diff_density_min -0.209 _refine_diff_density_rms 0.042 #=============================================================================== # 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 0.90364(5) 0.27263(15) 0.14089(6) 0.0157(2) Uani 1 1 d . . . O2 O 1.03980(5) 0.17678(15) 0.07805(6) 0.0156(2) Uani 1 1 d . . . O3 O 0.82897(5) -0.01015(16) -0.03528(6) 0.0165(2) Uani 1 1 d . . . O4 O 0.88816(5) 0.08462(16) 0.26038(6) 0.0208(3) Uani 1 1 d . . . O5 O 0.77636(5) 0.24612(17) -0.11716(7) 0.0241(3) Uani 1 1 d . . . C1 C 0.88928(7) 0.0727(2) 0.09210(8) 0.0149(3) Uani 1 1 d . . . C2 C 0.94889(7) -0.0911(2) 0.09589(8) 0.0149(3) Uani 1 1 d . . . C3 C 1.01131(7) -0.0250(2) 0.04558(8) 0.0132(3) Uani 1 1 d . . . C4 C 0.93452(7) 0.2077(2) -0.04780(8) 0.0147(3) Uani 1 1 d . . . C5 C 0.87167(7) 0.1600(2) 0.00410(8) 0.0148(3) Uani 1 1 d . . . C6 C 0.89844(7) 0.2566(2) 0.22392(8) 0.0160(3) Uani 1 1 d . . . C7 C 0.90691(8) 0.4738(2) 0.26687(9) 0.0194(3) Uani 1 1 d . . . C8 C 0.78365(7) 0.0566(2) -0.09615(8) 0.0180(3) Uani 1 1 d . . . C9 C 0.74413(8) -0.1344(3) -0.13197(10) 0.0241(4) Uani 1 1 d . . . H2O H 1.0683(10) 0.144(3) 0.1182(13) 0.039(5) Uiso 1 1 d . . . H1 H 0.8480(7) 0.009(2) 0.1146(9) 0.013(4) Uiso 1 1 d . . . H2A H 0.9644(7) -0.115(2) 0.1530(9) 0.012(4) Uiso 1 1 d . . . H2B H 0.9312(8) -0.231(3) 0.0755(10) 0.018(4) Uiso 1 1 d . . . H4A H 0.9543(8) 0.347(3) -0.0287(9) 0.014(4) Uiso 1 1 d . . . H4B H 0.9188(8) 0.233(2) -0.1050(10) 0.016(4) Uiso 1 1 d . . . H5 H 0.8439(7) 0.292(2) 0.0083(9) 0.010(4) Uiso 1 1 d . . . H7A H 0.9468(9) 0.468(3) 0.3057(11) 0.030(5) Uiso 1 1 d . . . H7B H 0.8671(10) 0.501(3) 0.2999(12) 0.038(5) Uiso 1 1 d . . . H7C H 0.9129(8) 0.593(3) 0.2292(11) 0.026(4) Uiso 1 1 d . . . H9A H 0.6992(11) -0.122(3) -0.1147(12) 0.045(6) Uiso 1 1 d . . . H9B H 0.7630(9) -0.275(3) -0.1137(11) 0.033(5) Uiso 1 1 d . . . H9C H 0.7429(10) -0.126(3) -0.1934(13) 0.045(6) 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 O1 0.0202(5) 0.0154(5) 0.0115(5) -0.0011(4) 0.0014(4) -0.0015(4) O2 0.0184(5) 0.0149(5) 0.0131(5) -0.0013(4) -0.0034(4) -0.0019(4) O3 0.0159(5) 0.0185(5) 0.0150(5) -0.0006(4) -0.0023(4) -0.0011(4) O4 0.0292(6) 0.0191(5) 0.0143(5) 0.0014(4) 0.0022(4) -0.0007(4) O5 0.0220(6) 0.0233(6) 0.0265(6) 0.0038(4) -0.0050(4) 0.0016(4) C1 0.0170(7) 0.0152(7) 0.0126(7) -0.0017(5) 0.0012(5) -0.0025(5) C2 0.0188(7) 0.0140(7) 0.0118(7) 0.0016(5) -0.0004(5) -0.0013(6) C3 0.0161(7) 0.0130(7) 0.0104(7) -0.0008(5) -0.0008(5) -0.0020(5) C4 0.0185(7) 0.0139(7) 0.0117(6) 0.0010(5) -0.0011(5) -0.0010(5) C5 0.0155(7) 0.0139(7) 0.0148(7) -0.0011(5) -0.0015(5) -0.0004(6) C6 0.0138(7) 0.0213(8) 0.0129(6) 0.0006(6) -0.0005(5) 0.0017(5) C7 0.0256(8) 0.0188(8) 0.0136(7) -0.0011(6) -0.0003(6) 0.0007(6) C8 0.0133(7) 0.0252(8) 0.0155(7) 0.0006(6) 0.0020(5) 0.0013(6) C9 0.0178(8) 0.0282(9) 0.0259(8) -0.0018(7) -0.0036(6) -0.0019(7) #=============================================================================== # 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 1.4665(16) . ? O1 C6 1.3387(17) . ? O2 C3 1.4363(16) . ? O2 H2O 0.86(2) . ? O3 C5 1.4568(16) . ? O3 C8 1.3538(16) . ? O4 C6 1.2172(17) . ? O5 C8 1.2078(18) . ? C1 H1 0.970(15) . ? C2 C1 1.527(2) . ? C2 C3 1.5306(19) . ? C2 H2A 0.964(15) . ? C2 H2B 0.971(16) . ? C4 H4A 0.975(15) . ? C4 H4B 0.968(16) . ? C5 C1 1.5326(18) . ? C5 C4 1.526(2) . ? C5 H5 0.973(15) . ? C6 C7 1.495(2) . ? C7 H7A 0.978(18) . ? C7 H7B 0.97(2) . ? C7 H7C 0.955(18) . ? C8 C9 1.496(2) . ? C9 H9A 0.93(2) . ? C9 H9B 0.974(19) . ? C9 H9C 0.98(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C2 112.86(11) . . ? O1 C1 C5 103.57(11) . . ? O1 C1 H1 106.2(9) . . ? O1 C6 C7 112.38(12) . . ? O2 C3 C2 109.69(10) . . ? O3 C5 C1 104.96(11) . . ? O3 C5 C4 110.75(11) . . ? O3 C5 H5 107.9(8) . . ? O3 C8 C9 110.89(13) . . ? O4 C6 O1 123.82(13) . . ? O4 C6 C7 123.80(12) . . ? O5 C8 O3 123.64(13) . . ? O5 C8 C9 125.47(13) . . ? C1 C2 C3 114.88(11) . . ? C1 C2 H2A 110.4(9) . . ? C1 C2 H2B 107.3(9) . . ? C1 C5 H5 109.3(8) . . ? C2 C1 C5 114.13(11) . . ? C2 C1 H1 111.1(9) . . ? C3 O2 H2O 107.7(13) . . ? C3 C2 H2A 108.0(9) . . ? C3 C2 H2B 109.4(9) . . ? C4 C5 C1 113.98(11) . . ? C4 C5 H5 109.7(8) . . ? C5 C1 H1 108.5(9) . . ? C5 C4 H4A 108.0(9) . . ? C5 C4 H4B 108.1(9) . . ? C6 O1 C1 116.64(10) . . ? C6 C7 H7A 109.6(10) . . ? C6 C7 H7B 109.1(11) . . ? C6 C7 H7C 113.4(10) . . ? C8 O3 C5 116.50(11) . . ? C8 C9 H9A 107.2(12) . . ? C8 C9 H9B 112.7(11) . . ? C8 C9 H9C 109.6(11) . . ? H2B C2 H2A 106.5(12) . . ? H4B C4 H4A 105.5(12) . . ? H7A C7 H7B 107.0(15) . . ? H7A C7 H7C 108.5(14) . . ? H7B C7 H7C 109.2(15) . . ? H9B C9 H9A 109.4(16) . . ? H9B C9 H9C 110.2(15) . . ? H9C C9 H9A 107.5(16) . . ? 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 C5 C1 O1 -155.46(10) . . . . ? O3 C5 C1 C2 81.45(13) . . . . ? C1 O1 C6 O4 6.08(19) . . . . ? C1 O1 C6 C7 -174.09(11) . . . . ? C1 C2 C3 O2 61.96(14) . . . . ? C3 C2 C1 O1 -73.19(14) . . . . ? C3 C2 C1 C5 44.70(16) . . . . ? C4 C5 C1 O1 83.19(13) . . . . ? C4 C5 C1 C2 -39.90(16) . . . . ? C5 O3 C8 O5 -1.65(19) . . . . ? C5 O3 C8 C9 179.09(11) . . . . ? C6 O1 C1 C2 -77.40(14) . . . . ? C6 O1 C1 C5 158.67(11) . . . . ? C8 O3 C5 C1 152.92(11) . . . . ? C8 O3 C5 C4 -83.63(14) . . . . ? 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 # # Hydrogen bonding scheme # ======== ======= ====== # # D H A D - H H...A D...A D - H...A symm(A) # - - - ----- ----- ----- --------- ------- O2 H2O O4 0.86(2) 2.12(2) 2.9526(15) 162.3(18) 2_755 yes #===END