# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2004 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Dr Mark Elsegood' _publ_contact_author_address ; Chemistry Department Loughborough University Loughborough LE11 3TU UNITED KINGDOM ; _publ_contact_author_email M.R.J.ELSEGOOD@LBORO.AC.UK _publ_section_title ; Step-wise dis-assembly of trimesic acid: Mono and bis(methanol) solvates. ; loop_ _publ_author_name 'Mark Elsegood' 'Sophie H. Dale' 'Simon J. Richards' data_1 _database_code_depnum_ccdc_archive 'CCDC 233070' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H10 O7' _chemical_formula_weight 242.18 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.8770(10) _cell_length_b 8.9629(11) _cell_length_c 8.9562(11) _cell_angle_alpha 111.926(3) _cell_angle_beta 96.722(3) _cell_angle_gamma 110.575(3) _cell_volume 526.24(11) _cell_formula_units_Z 2 _cell_measurement_temperature 160(2) _cell_measurement_reflns_used 3043 _cell_measurement_theta_min 2.55 _cell_measurement_theta_max 28.72 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.528 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 252 _exptl_absorpt_coefficient_mu 0.133 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.948 _exptl_absorpt_correction_T_max 0.964 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 160(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Siemens SMART 1K CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 3969 _diffrn_reflns_av_R_equivalents 0.0173 _diffrn_reflns_av_sigmaI/netI 0.0306 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.56 _diffrn_reflns_theta_max 28.79 _reflns_number_total 2380 _reflns_number_gt 1984 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Siemens SMART' _computing_cell_refinement 'local programs' _computing_data_reduction 'Siemens SAINT' _computing_structure_solution 'Siemens SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL and local programs' _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^)+(0.0685P)^2^+0.0691P] 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 SHELXL _refine_ls_extinction_coef 0.014(11) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2380 _refine_ls_number_parameters 160 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0464 _refine_ls_R_factor_gt 0.0388 _refine_ls_wR_factor_ref 0.1140 _refine_ls_wR_factor_gt 0.1100 _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_restrained_S_all 1.073 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.18263(17) 0.96666(16) 0.38557(16) 0.0163(3) Uani 1 1 d . . . C2 C 0.00763(18) 0.81901(17) 0.31211(16) 0.0171(3) Uani 1 1 d . . . H2 H -0.0700 0.7900 0.2067 0.021 Uiso 1 1 calc R . . C3 C -0.05265(17) 0.71376(16) 0.39502(16) 0.0167(3) Uani 1 1 d . . . C4 C 0.06124(18) 0.75645(17) 0.54918(16) 0.0178(3) Uani 1 1 d . . . H4 H 0.0206 0.6837 0.6043 0.021 Uiso 1 1 calc R . . C5 C 0.23506(18) 0.90600(17) 0.62302(16) 0.0177(3) Uani 1 1 d . . . C6 C 0.29590(18) 1.01097(17) 0.54114(16) 0.0179(3) Uani 1 1 d . . . H6 H 0.4145 1.1127 0.5912 0.021 Uiso 1 1 calc R . . C7 C 0.25283(18) 1.08808(17) 0.30659(16) 0.0182(3) Uani 1 1 d . . . O1 O 0.40917(13) 1.21348(13) 0.37156(13) 0.0272(3) Uani 1 1 d . . . O2 O 0.13495(14) 1.04991(13) 0.16846(12) 0.0271(3) Uani 1 1 d . . . H2A H 0.1815 1.1272 0.1350 0.041 Uiso 1 1 calc R . . C8 C -0.24525(18) 0.56155(17) 0.32101(17) 0.0189(3) Uani 1 1 d . . . O3 O -0.34855(14) 0.51445(14) 0.18539(13) 0.0307(3) Uani 1 1 d . . . O4 O -0.28828(14) 0.48825(13) 0.42284(12) 0.0252(3) Uani 1 1 d . . . H4A H -0.3982 0.4054 0.3791 0.038 Uiso 1 1 calc R . . C9 C 0.34977(18) 0.95106(17) 0.79074(16) 0.0188(3) Uani 1 1 d . . . O5 O 0.29997(14) 0.85324(13) 0.85890(12) 0.0249(3) Uani 1 1 d . . . O6 O 0.50425(14) 1.10053(13) 0.85702(12) 0.0260(3) Uani 1 1 d . . . H6A H 0.5647 1.1143 0.9485 0.039 Uiso 1 1 calc R . . O7 O 0.26079(14) 1.30363(14) 0.07832(14) 0.0303(3) Uani 1 1 d . . . H7 H 0.3791 1.3534 0.0999 0.045 Uiso 1 1 calc R . . C10 C 0.1921(3) 1.4357(2) 0.1447(2) 0.0406(4) Uani 1 1 d . . . H10A H 0.2525 1.5056 0.2660 0.061 Uiso 1 1 calc R . . H10B H 0.0547 1.3773 0.1233 0.061 Uiso 1 1 calc R . . H10C H 0.2219 1.5146 0.0903 0.061 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 C1 0.0150(6) 0.0177(6) 0.0166(6) 0.0093(5) 0.0055(5) 0.0054(5) C2 0.0155(6) 0.0206(6) 0.0146(6) 0.0089(5) 0.0034(5) 0.0061(5) C3 0.0148(6) 0.0167(6) 0.0165(6) 0.0078(5) 0.0041(5) 0.0042(5) C4 0.0173(6) 0.0186(6) 0.0190(7) 0.0113(5) 0.0057(5) 0.0061(5) C5 0.0163(6) 0.0204(6) 0.0155(6) 0.0086(5) 0.0034(5) 0.0067(5) C6 0.0145(6) 0.0187(6) 0.0173(6) 0.0082(5) 0.0032(5) 0.0041(5) C7 0.0175(6) 0.0198(6) 0.0177(6) 0.0099(5) 0.0058(5) 0.0065(5) O1 0.0188(5) 0.0266(5) 0.0301(6) 0.0184(5) 0.0013(4) -0.0012(4) O2 0.0237(5) 0.0301(5) 0.0226(5) 0.0193(5) 0.0006(4) 0.0002(4) C8 0.0164(6) 0.0182(6) 0.0198(7) 0.0100(5) 0.0039(5) 0.0039(5) O3 0.0207(5) 0.0338(6) 0.0261(6) 0.0186(5) -0.0043(4) -0.0028(4) O4 0.0212(5) 0.0232(5) 0.0215(5) 0.0137(4) 0.0012(4) -0.0035(4) C9 0.0174(6) 0.0212(6) 0.0163(6) 0.0090(5) 0.0039(5) 0.0065(5) O5 0.0234(5) 0.0287(5) 0.0186(5) 0.0145(4) 0.0011(4) 0.0041(4) O6 0.0233(5) 0.0253(5) 0.0176(5) 0.0103(4) -0.0046(4) 0.0003(4) O7 0.0205(5) 0.0357(6) 0.0315(6) 0.0241(5) 0.0011(4) 0.0008(4) C10 0.0440(10) 0.0463(10) 0.0331(9) 0.0224(8) 0.0130(8) 0.0154(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.3927(17) . ? C1 C6 1.3936(17) . ? C1 C7 1.4946(17) . ? C2 C3 1.3992(17) . ? C3 C4 1.3899(18) . ? C3 C8 1.4956(17) . ? C4 C5 1.3945(18) . ? C5 C6 1.3903(17) . ? C5 C9 1.4862(17) . ? C7 O1 1.2204(16) . ? C7 O2 1.3044(15) . ? C8 O3 1.2083(16) . ? C8 O4 1.3197(15) . ? C9 O5 1.2285(15) . ? C9 O6 1.3111(15) . ? O7 C10 1.431(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 120.50(11) . . ? C2 C1 C7 122.11(11) . . ? C6 C1 C7 117.33(11) . . ? C1 C2 C3 119.35(11) . . ? C4 C3 C2 120.21(12) . . ? C4 C3 C8 120.38(11) . . ? C2 C3 C8 119.31(11) . . ? C3 C4 C5 120.07(11) . . ? C6 C5 C4 119.98(11) . . ? C6 C5 C9 121.48(11) . . ? C4 C5 C9 118.52(11) . . ? C5 C6 C1 119.86(12) . . ? O1 C7 O2 124.34(11) . . ? O1 C7 C1 120.57(11) . . ? O2 C7 C1 115.08(11) . . ? O3 C8 O4 124.72(12) . . ? O3 C8 C3 123.53(12) . . ? O4 C8 C3 111.74(11) . . ? O5 C9 O6 124.00(11) . . ? O5 C9 C5 121.23(12) . . ? O6 C9 C5 114.77(11) . . ? 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 C6 C1 C2 C3 -0.8(2) . . . . ? C7 C1 C2 C3 -177.96(11) . . . . ? C1 C2 C3 C4 0.0(2) . . . . ? C1 C2 C3 C8 176.46(12) . . . . ? C2 C3 C4 C5 0.9(2) . . . . ? C8 C3 C4 C5 -175.49(11) . . . . ? C3 C4 C5 C6 -1.0(2) . . . . ? C3 C4 C5 C9 177.83(11) . . . . ? C4 C5 C6 C1 0.2(2) . . . . ? C9 C5 C6 C1 -178.63(12) . . . . ? C2 C1 C6 C5 0.7(2) . . . . ? C7 C1 C6 C5 178.00(12) . . . . ? C2 C1 C7 O1 -177.87(12) . . . . ? C6 C1 C7 O1 4.9(2) . . . . ? C2 C1 C7 O2 2.87(19) . . . . ? C6 C1 C7 O2 -174.33(12) . . . . ? C4 C3 C8 O3 -177.67(13) . . . . ? C2 C3 C8 O3 5.9(2) . . . . ? C4 C3 C8 O4 3.34(18) . . . . ? C2 C3 C8 O4 -173.10(11) . . . . ? C6 C5 C9 O5 -176.37(12) . . . . ? C4 C5 C9 O5 4.8(2) . . . . ? C6 C5 C9 O6 3.69(19) . . . . ? C4 C5 C9 O6 -175.14(12) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2 H2A O7 0.84 1.77 2.6037(13) 172.2 . O4 H4A O1 0.84 1.82 2.5941(13) 152.0 1_445 O6 H6A O5 0.84 1.78 2.6208(13) 178.1 2_677 O7 H7 O3 0.84 1.97 2.7979(14) 167.7 1_665 _diffrn_measured_fraction_theta_max 0.870 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.378 _refine_diff_density_min -0.227 _refine_diff_density_rms 0.050 #===END of DATA for 1 data_2 _database_code_depnum_ccdc_archive 'CCDC 233071' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H14 O8' _chemical_formula_weight 274.22 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 3.7519(9) _cell_length_b 9.579(2) _cell_length_c 17.732(4) _cell_angle_alpha 91.206(6) _cell_angle_beta 91.881(6) _cell_angle_gamma 93.998(5) _cell_volume 635.2(3) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2968 _cell_measurement_theta_min 2.13 _cell_measurement_theta_max 28.70 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.67 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.434 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 288 _exptl_absorpt_coefficient_mu 0.124 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.921 _exptl_absorpt_correction_T_max 0.986 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1K CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 3936 _diffrn_reflns_av_R_equivalents 0.0238 _diffrn_reflns_av_sigmaI/netI 0.0432 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.15 _diffrn_reflns_theta_max 24.99 _reflns_number_total 2215 _reflns_number_gt 1803 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'local programs' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL and local programs' _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^)+(0.0139P)^2^+2.2603P] 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 SHELXL _refine_ls_extinction_coef 0.058(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2215 _refine_ls_number_parameters 195 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0914 _refine_ls_R_factor_gt 0.0780 _refine_ls_wR_factor_ref 0.1816 _refine_ls_wR_factor_gt 0.1767 _refine_ls_goodness_of_fit_ref 1.227 _refine_ls_restrained_S_all 1.227 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.9223(11) 0.2483(4) 0.3093(2) 0.0216(9) Uani 1 1 d . . . H1A H 1.0429 0.2474 0.3572 0.026 Uiso 1 1 calc R . . C2 C 0.8149(11) 0.1231(4) 0.2714(2) 0.0221(9) Uani 1 1 d . . . C3 C 0.6492(11) 0.1257(4) 0.2006(2) 0.0226(10) Uani 1 1 d . . . H3 H 0.5822 0.0401 0.1742 0.027 Uiso 1 1 calc R . . C4 C 0.5793(11) 0.2519(4) 0.1675(2) 0.0209(9) Uani 1 1 d . . . C5 C 0.6836(11) 0.3763(4) 0.2058(2) 0.0223(10) Uani 1 1 d . . . H5 H 0.6399 0.4631 0.1836 0.027 Uiso 1 1 calc R . . C6 C 0.8529(11) 0.3745(4) 0.2770(2) 0.0224(9) Uani 1 1 d . . . C7 C 0.3967(12) 0.2532(4) 0.0916(2) 0.0247(10) Uani 1 1 d . . . O1 O 0.3195(10) 0.1375(3) 0.05827(18) 0.0392(9) Uani 1 1 d . . . H1 H 0.2146 0.1506 0.0167 0.059 Uiso 0.507(8) 1 calc PR A 1 O2 O 0.3278(10) 0.3698(3) 0.06466(18) 0.0366(9) Uani 1 1 d . . . H2 H 0.2412 0.3574 0.0205 0.055 Uiso 0.493(8) 1 calc PR A 2 C8 C 0.8965(12) -0.0129(4) 0.3063(2) 0.0254(10) Uani 1 1 d . . . O3 O 0.7569(10) -0.1211(3) 0.26654(19) 0.0363(9) Uani 1 1 d . . . H3A H 0.810(15) -0.201(6) 0.287(3) 0.055 Uiso 1 1 d . . . O4 O 1.0696(9) -0.0190(3) 0.36486(17) 0.0311(8) Uani 1 1 d . . . C9 C 0.9679(12) 0.5125(4) 0.3161(2) 0.0257(10) Uani 1 1 d . . . O5 O 1.1381(10) 0.5014(3) 0.38096(18) 0.0349(9) Uani 1 1 d . . . H5A H 1.2315 0.5803 0.3951 0.052 Uiso 1 1 calc R . . O6 O 0.9035(10) 0.6216(3) 0.28764(19) 0.0394(9) Uani 1 1 d . . . O7 O 1.3593(11) -0.2507(3) 0.42785(19) 0.0418(10) Uani 1 1 d . . . H7 H 1.2604 -0.1826 0.4093 0.063 Uiso 1 1 calc R . . C10 C 1.5150(15) -0.2110(6) 0.4992(3) 0.0446(14) Uani 1 1 d . . . H10A H 1.7071 -0.1378 0.4933 0.067 Uiso 1 1 calc R . . H10B H 1.6133 -0.2924 0.5226 0.067 Uiso 1 1 calc R . . H10C H 1.3326 -0.1753 0.5314 0.067 Uiso 1 1 calc R . . C11A C -0.1556(15) 0.2541(6) -0.1003(3) 0.0433(13) Uani 0.507(8) 1 d P A 1 H11A H -0.4131 0.2422 -0.0924 0.065 Uiso 0.507(8) 1 calc PR A 1 H11B H -0.1146 0.2644 -0.1543 0.065 Uiso 0.507(8) 1 calc PR A 1 H11C H -0.0541 0.3379 -0.0726 0.065 Uiso 0.507(8) 1 calc PR A 1 O8A O 0.025(2) 0.1251(7) -0.0717(4) 0.039(2) Uani 0.507(8) 1 d P A 1 H8A H -0.1308 0.0588 -0.0670 0.058 Uiso 0.507(8) 1 calc PR A 1 C11B C -0.1556(15) 0.2541(6) -0.1003(3) 0.0433(13) Uani 0.493(8) 1 d P A 2 H11D H 0.0202 0.1851 -0.1094 0.065 Uiso 0.493(8) 1 calc PR A 2 H11E H -0.2702 0.2776 -0.1484 0.065 Uiso 0.493(8) 1 calc PR A 2 H11F H -0.3373 0.2148 -0.0668 0.065 Uiso 0.493(8) 1 calc PR A 2 O8B O 0.027(2) 0.3824(7) -0.0646(4) 0.038(2) Uani 0.493(8) 1 d P A 2 H8B H -0.1200 0.4443 -0.0606 0.057 Uiso 0.493(8) 1 calc PR A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.023(2) 0.020(2) 0.022(2) 0.0031(17) -0.0035(17) 0.0035(17) C2 0.022(2) 0.017(2) 0.027(2) 0.0019(17) 0.0012(18) 0.0040(17) C3 0.026(2) 0.017(2) 0.025(2) -0.0013(17) 0.0004(18) 0.0026(17) C4 0.020(2) 0.019(2) 0.023(2) 0.0028(17) -0.0002(17) 0.0019(17) C5 0.025(2) 0.016(2) 0.026(2) 0.0033(17) -0.0010(18) 0.0049(17) C6 0.024(2) 0.020(2) 0.024(2) 0.0012(17) 0.0014(18) 0.0009(17) C7 0.029(2) 0.021(2) 0.025(2) 0.0046(18) 0.0005(19) 0.0027(18) O1 0.061(3) 0.0234(18) 0.0306(19) 0.0002(14) -0.0128(17) -0.0059(16) O2 0.057(2) 0.0260(18) 0.0279(18) 0.0052(14) -0.0086(16) 0.0156(16) C8 0.033(3) 0.018(2) 0.025(2) 0.0027(18) 0.002(2) 0.0026(19) O3 0.059(2) 0.0141(15) 0.0352(19) 0.0007(14) -0.0179(17) 0.0035(15) O4 0.043(2) 0.0219(16) 0.0275(17) 0.0030(13) -0.0124(15) 0.0045(14) C9 0.034(3) 0.019(2) 0.025(2) 0.0000(18) -0.0009(19) 0.0025(19) O5 0.054(2) 0.0176(16) 0.0320(19) -0.0031(13) -0.0144(16) 0.0015(15) O6 0.061(2) 0.0155(16) 0.041(2) 0.0002(14) -0.0151(17) 0.0069(15) O7 0.065(3) 0.0210(17) 0.038(2) -0.0006(14) -0.0276(18) 0.0055(16) C10 0.048(3) 0.057(4) 0.028(3) 0.001(2) -0.014(2) 0.001(3) C11A 0.045(3) 0.048(3) 0.035(3) 0.003(2) -0.007(2) -0.004(3) O8A 0.056(5) 0.027(4) 0.030(4) 0.007(3) -0.009(3) -0.008(3) C11B 0.045(3) 0.048(3) 0.035(3) 0.003(2) -0.007(2) -0.004(3) O8B 0.050(5) 0.026(4) 0.037(4) 0.003(3) -0.013(3) 0.007(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.386(6) . ? C1 C2 1.391(6) . ? C2 C3 1.384(6) . ? C2 C8 1.500(6) . ? C3 C4 1.392(6) . ? C4 C5 1.385(6) . ? C4 C7 1.492(6) . ? C5 C6 1.395(6) . ? C6 C9 1.509(6) . ? C7 O1 1.255(5) . ? C7 O2 1.264(5) . ? C8 O4 1.212(5) . ? C8 O3 1.309(5) . ? C9 O6 1.206(5) . ? C9 O5 1.307(5) . ? O7 C10 1.410(6) . ? C11A O8A 1.537(8) . ? 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 C6 C1 C2 119.8(4) . . ? C3 C2 C1 119.6(4) . . ? C3 C2 C8 120.9(4) . . ? C1 C2 C8 119.4(4) . . ? C2 C3 C4 121.0(4) . . ? C5 C4 C3 119.1(4) . . ? C5 C4 C7 120.4(4) . . ? C3 C4 C7 120.4(4) . . ? C4 C5 C6 120.2(4) . . ? C1 C6 C5 120.2(4) . . ? C1 C6 C9 121.3(4) . . ? C5 C6 C9 118.4(4) . . ? O1 C7 O2 123.9(4) . . ? O1 C7 C4 117.7(4) . . ? O2 C7 C4 118.4(4) . . ? O4 C8 O3 125.0(4) . . ? O4 C8 C2 122.8(4) . . ? O3 C8 C2 112.2(4) . . ? O6 C9 O5 124.8(4) . . ? O6 C9 C6 120.8(4) . . ? O5 C9 C6 114.4(4) . . ? 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 C6 C1 C2 C3 2.0(6) . . . . ? C6 C1 C2 C8 179.0(4) . . . . ? C1 C2 C3 C4 -1.8(7) . . . . ? C8 C2 C3 C4 -178.8(4) . . . . ? C2 C3 C4 C5 1.2(6) . . . . ? C2 C3 C4 C7 -179.3(4) . . . . ? C3 C4 C5 C6 -0.7(6) . . . . ? C7 C4 C5 C6 179.7(4) . . . . ? C2 C1 C6 C5 -1.6(6) . . . . ? C2 C1 C6 C9 -179.5(4) . . . . ? C4 C5 C6 C1 0.9(6) . . . . ? C4 C5 C6 C9 178.9(4) . . . . ? C5 C4 C7 O1 177.5(4) . . . . ? C3 C4 C7 O1 -2.1(6) . . . . ? C5 C4 C7 O2 -2.7(6) . . . . ? C3 C4 C7 O2 177.7(4) . . . . ? C3 C2 C8 O4 173.1(4) . . . . ? C1 C2 C8 O4 -3.9(7) . . . . ? C3 C2 C8 O3 -7.5(6) . . . . ? C1 C2 C8 O3 175.5(4) . . . . ? C1 C6 C9 O6 -179.4(5) . . . . ? C5 C6 C9 O6 2.6(7) . . . . ? C1 C6 C9 O5 0.8(6) . . . . ? C5 C6 C9 O5 -177.2(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1 O8A 0.84 1.71 2.521(7) 162.6 . O2 H2 O8B 0.84 1.72 2.531(7) 162.7 . O7 H7 O4 0.84 1.94 2.777(4) 175.4 . O3 H3A O6 0.88(6) 1.76(6) 2.594(4) 156(6) 1_545 O5 H5A O7 0.84 1.74 2.572(4) 171.3 1_565 O8A H8A O1 0.84 1.97 2.765(7) 156.8 2 O8B H8B O2 0.84 2.00 2.801(7) 160.4 2_565 _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.310 _refine_diff_density_min -0.295 _refine_diff_density_rms 0.070 #===END OF DATA FOR 2 #===END OF CIF FILE