# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2005 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'J. Veciana' 'Neus Domingo' 'Daniel Maspoch' 'Nans Roques' 'Concepcio Rovira' 'Daniel Ruiz-Molina' 'Javier Tejada' 'Klaus Wurst' _publ_contact_author_name 'Prof J Veciana' _publ_contact_author_address ; Campus Universitari Institut de Ciencia de Materials de Barcelona Cerdanyola Barcelona 08193 SPAIN ; _publ_contact_author_email VECIANAJ@ICMAB.ES _publ_requested_journal 'Chemical Communications' _publ_section_title ; Hydrogen-bonded self-assemblies in a polychlorotriphenylmethyl radical derivative substituted with six meta-carboxylic acid groups ; data_haetoet _database_code_depnum_ccdc_archive 'CCDC 276958' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C37 H36 Cl9 O15' _chemical_formula_weight 1039.71 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting trigonal _symmetry_space_group_name_H-M R-3 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' _cell_length_a 15.6488(8) _cell_length_b 15.6488(6) _cell_length_c 33.8402(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 7176.7(5) _cell_formula_units_Z 6 _cell_measurement_temperature 233(2) _cell_measurement_reflns_used 49037 _cell_measurement_theta_min 1.0 _cell_measurement_theta_max 23.5 _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.443 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3186 _exptl_absorpt_coefficient_mu 0.588 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 233(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'phi- and omega-scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 12097 _diffrn_reflns_av_R_equivalents 0.0266 _diffrn_reflns_av_sigmaI/netI 0.0174 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -37 _diffrn_reflns_limit_l_max 37 _diffrn_reflns_theta_min 1.81 _diffrn_reflns_theta_max 22.97 _reflns_number_total 2211 _reflns_number_gt 1880 _reflns_threshold_expression >2sigma(I) _computing_data_collection KappaCCD _computing_cell_refinement ? _computing_data_reduction 'DENZO and SCALEPACK' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0971P)^2^+24.8878P] 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 'riding, refined at O2, O4 with restraints' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2211 _refine_ls_number_parameters 192 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0679 _refine_ls_R_factor_gt 0.0588 _refine_ls_wR_factor_ref 0.1703 _refine_ls_wR_factor_gt 0.1624 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _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 O1 O -0.0004(2) 0.2965(3) 0.10519(9) 0.0820(10) Uani 1 1 d . . . O2 O 0.1189(3) 0.3089(3) 0.14393(9) 0.0774(10) Uani 1 1 d D . . H2O H 0.071(4) 0.281(6) 0.161(2) 0.16(3) Uiso 1 1 d D . . O3 O 0.3528(3) 0.3353(3) -0.00170(10) 0.0878(11) Uani 1 1 d . . . O4 O 0.2522(3) 0.3628(3) -0.03904(10) 0.0874(11) Uani 1 1 d D . . H4O H 0.273(3) 0.339(3) -0.0570(11) 0.073(14) Uiso 1 1 d D . . Cl1 Cl 0.18028(8) 0.54265(8) 0.12580(3) 0.0607(4) Uani 1 1 d . . . Cl2 Cl 0.40389(10) 0.58061(9) -0.00278(4) 0.0812(5) Uani 1 1 d . . . Cl3 Cl 0.13269(12) 0.22505(9) 0.04794(4) 0.0897(5) Uani 1 1 d . . . C1 C 0.0856(3) 0.3272(3) 0.11226(12) 0.0592(11) Uani 1 1 d . . . C2 C 0.2970(4) 0.3653(3) -0.00595(13) 0.0648(12) Uani 1 1 d . . . C3 C 0.3333 0.6667 0.0649(2) 0.0561(17) Uani 1 3 d S . . C4 C 0.1663(3) 0.3927(3) 0.08385(11) 0.0509(10) Uani 1 1 d . . . C5 C 0.2143(3) 0.4943(3) 0.08701(10) 0.0466(9) Uani 1 1 d . . . C6 C 0.2888(3) 0.5583(3) 0.06090(10) 0.0446(9) Uani 1 1 d . . . C7 C 0.3143(3) 0.5116(3) 0.03160(11) 0.0509(9) Uani 1 1 d . . . C8 C 0.2677(3) 0.4101(3) 0.02703(11) 0.0525(10) Uani 1 1 d . . . C9 C 0.1933(3) 0.3513(3) 0.05349(12) 0.0577(10) Uani 1 1 d . . . O5 O -0.0123(3) 0.1808(4) 0.19381(13) 0.1184(16) Uani 1 1 d . . . C10 C -0.0970(7) 0.0880(8) 0.1850(4) 0.182(5) Uani 1 1 d . . . H10A H -0.1553 0.0870 0.1961 0.218 Uiso 1 1 calc . . . H10B H -0.0901 0.0359 0.1981 0.218 Uiso 1 1 calc . . . C11 C -0.1132(11) 0.0658(7) 0.1434(5) 0.226(7) Uani 1 1 d . . . H11A H -0.1718 0.0018 0.1398 0.339 Uiso 1 1 calc . . . H11B H -0.0566 0.0649 0.1322 0.339 Uiso 1 1 calc . . . H11C H -0.1222 0.1159 0.1302 0.339 Uiso 1 1 calc . . . C12 C 0.0049(8) 0.2066(10) 0.2340(2) 0.166(4) Uani 1 1 d . . . H12A H -0.0491 0.2152 0.2441 0.199 Uiso 1 1 calc . . . H12B H 0.0041 0.1522 0.2487 0.199 Uiso 1 1 calc . . . C13 C 0.0932(11) 0.2918(7) 0.2411(2) 0.198(6) Uani 1 1 d . . . H13A H 0.0996 0.3065 0.2692 0.297 Uiso 1 1 calc . . . H13B H 0.0948 0.3461 0.2266 0.297 Uiso 1 1 calc . . . H13C H 0.1473 0.2828 0.2325 0.297 Uiso 1 1 calc . . . 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 0.058(2) 0.104(3) 0.0561(18) 0.0168(17) -0.0046(15) 0.0191(18) O2 0.081(2) 0.091(2) 0.0528(19) 0.0164(16) -0.0061(17) 0.0372(19) O3 0.104(3) 0.115(3) 0.078(2) -0.025(2) -0.0120(19) 0.081(3) O4 0.119(3) 0.127(3) 0.055(2) -0.0293(19) -0.0160(19) 0.091(3) Cl1 0.0678(7) 0.0694(7) 0.0455(6) -0.0062(5) 0.0091(5) 0.0346(5) Cl2 0.0868(9) 0.0720(8) 0.0678(8) -0.0028(6) 0.0353(6) 0.0269(6) Cl3 0.1128(11) 0.0517(7) 0.0914(10) -0.0056(6) 0.0082(8) 0.0313(7) C1 0.058(3) 0.063(3) 0.050(2) -0.0024(19) -0.010(2) 0.025(2) C2 0.074(3) 0.071(3) 0.059(3) -0.014(2) -0.001(2) 0.043(3) C3 0.046(2) 0.046(2) 0.077(5) 0.000 0.000 0.0228(11) C4 0.050(2) 0.056(2) 0.042(2) 0.0037(17) -0.0028(17) 0.0231(19) C5 0.050(2) 0.052(2) 0.0387(19) -0.0037(16) -0.0010(16) 0.0269(18) C6 0.048(2) 0.049(2) 0.0400(19) -0.0006(16) 0.0006(16) 0.0264(18) C7 0.051(2) 0.055(2) 0.046(2) 0.0029(17) 0.0050(17) 0.0255(19) C8 0.059(2) 0.058(2) 0.047(2) -0.0059(18) -0.0012(18) 0.034(2) C9 0.070(3) 0.053(2) 0.052(2) -0.0047(19) -0.004(2) 0.032(2) O5 0.115(3) 0.127(4) 0.079(3) 0.032(2) 0.013(2) 0.035(3) C10 0.103(6) 0.132(8) 0.227(13) 0.060(8) 0.018(7) -0.003(5) C11 0.266(16) 0.105(7) 0.239(14) -0.027(8) -0.123(12) 0.041(8) C12 0.181(9) 0.200(11) 0.086(5) 0.039(6) 0.031(6) 0.072(8) C13 0.313(15) 0.098(6) 0.087(5) -0.006(4) 0.032(7) 0.030(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.205(5) . ? O2 H2O 0.88(3) . ? O2 C1 1.285(5) . ? O3 C2 1.189(5) . ? O4 H4O 0.86(3) . ? O4 C2 1.311(6) . ? Cl1 C5 1.727(4) . ? Cl2 C7 1.724(4) . ? Cl3 C9 1.722(4) . ? C1 C4 1.508(6) . ? C2 C8 1.506(6) . ? C3 C6 1.483(4) 3_565 ? C3 C6 1.483(4) 2_665 ? C3 C6 1.483(4) . ? C4 C5 1.381(5) . ? C4 C9 1.387(6) . ? C5 C6 1.406(5) . ? C6 C7 1.403(5) . ? C7 C8 1.386(6) . ? C8 C9 1.390(6) . ? O5 C12 1.407(10) . ? O5 C10 1.424(10) . ? C10 C11 1.443(17) . ? C12 C13 1.380(14) . ? 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 H2O O2 C1 109(5) . . ? H4O O4 C2 108(3) . . ? O1 C1 O2 125.0(4) . . ? O1 C1 C4 122.2(4) . . ? O2 C1 C4 112.8(4) . . ? O3 C2 O4 125.4(4) . . ? O3 C2 C8 123.3(4) . . ? O4 C2 C8 111.3(4) . . ? C6 C3 C6 119.16(11) 3_565 2_665 ? C6 C3 C6 119.16(11) 3_565 . ? C6 C3 C6 119.16(11) 2_665 . ? C5 C4 C9 118.5(4) . . ? C5 C4 C1 121.4(4) . . ? C9 C4 C1 120.1(4) . . ? C4 C5 C6 123.5(3) . . ? C4 C5 Cl1 117.0(3) . . ? C6 C5 Cl1 119.5(3) . . ? C7 C6 C5 115.1(3) . . ? C7 C6 C3 124.6(4) . . ? C5 C6 C3 120.4(4) . . ? C8 C7 C6 123.5(3) . . ? C8 C7 Cl2 116.1(3) . . ? C6 C7 Cl2 120.3(3) . . ? C7 C8 C9 118.2(3) . . ? C7 C8 C2 120.5(4) . . ? C9 C8 C2 121.3(4) . . ? C4 C9 C8 121.2(4) . . ? C4 C9 Cl3 119.7(3) . . ? C8 C9 Cl3 119.1(3) . . ? C12 O5 C10 116.2(8) . . ? O5 C10 C11 114.3(9) . . ? C13 C12 O5 113.6(7) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 22.97 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.852 _refine_diff_density_min -0.411 _refine_diff_density_rms 0.063 data_hathf _database_code_depnum_ccdc_archive 'CCDC 276959' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C49 H54 Cl9 O18' _chemical_formula_weight 1249.97 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting trigonal _symmetry_space_group_name_H-M R-3 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' _cell_length_a 24.9133(6) _cell_length_b 24.9133(8) _cell_length_c 15.0874(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 8109.7(5) _cell_formula_units_Z 6 _cell_measurement_temperature 233(2) _cell_measurement_reflns_used 20258 _cell_measurement_theta_min 1.0 _cell_measurement_theta_max 22.5 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.536 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3870 _exptl_absorpt_coefficient_mu 0.539 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 233(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'phi- and omega-scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 13298 _diffrn_reflns_av_R_equivalents 0.0504 _diffrn_reflns_av_sigmaI/netI 0.0276 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.65 _diffrn_reflns_theta_max 22.50 _reflns_number_total 2347 _reflns_number_gt 1761 _reflns_threshold_expression >2sigma(I) _computing_data_collection KappaCCD _computing_cell_refinement ? _computing_data_reduction 'DENZO and SCALEPACK' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Small good crystal with low diffraction. Disorder of both THF-molecules. For C10-C13-O5 the disorder was not solved. For C14-C17-O6 a 1:1 position disorder model with partial overlying position (C15=C15A and C17=C17A) and bond restraints was used. Hydrogen atoms of both THF-molecules were not found and not calculated. ; _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^)+(0.1163P)^2^+25.5481P] 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 'found and refined at O2, O4 with restraints' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2347 _refine_ls_number_parameters 224 _refine_ls_number_restraints 21 _refine_ls_R_factor_all 0.0903 _refine_ls_R_factor_gt 0.0678 _refine_ls_wR_factor_ref 0.2055 _refine_ls_wR_factor_gt 0.1884 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.048 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.2320(3) 1.0375(4) 0.1167(4) 0.155(2) Uani 1 1 d . . . O2 O 0.1596(3) 0.9604(4) 0.0426(4) 0.140(2) Uani 1 1 d D . . H2O H 0.183(5) 0.980(5) -0.003(5) 0.21(5) Uiso 1 1 d D . . O3 O 0.0618(3) 0.8230(2) 0.3897(3) 0.1138(16) Uani 1 1 d . . . O4 O 0.1180(3) 0.9106(3) 0.4614(4) 0.138(2) Uani 1 1 d D . . H4O H 0.111(5) 0.886(2) 0.507(3) 0.23(6) Uiso 1 1 d D . . Cl1 Cl 0.09807(7) 1.04705(7) 0.10290(9) 0.0797(5) Uani 1 1 d . . . Cl2 Cl -0.00928(6) 0.91248(6) 0.40013(8) 0.0720(5) Uani 1 1 d . . . Cl3 Cl 0.18668(9) 0.91356(10) 0.25670(13) 0.1112(7) Uani 1 1 d . . . C1 C 0.1816(4) 0.9951(4) 0.1101(5) 0.099(2) Uani 1 1 d . . . C2 C 0.0871(3) 0.8777(4) 0.3939(4) 0.0868(18) Uani 1 1 d D . . C3 C 0.0000 1.0000 0.2490(6) 0.066(2) Uani 1 3 d S . . C4 C 0.1349(2) 0.9774(3) 0.1867(4) 0.0727(15) Uani 1 1 d . . . C5 C 0.0929(2) 0.9978(2) 0.1876(3) 0.0605(12) Uani 1 1 d . . . C6 C 0.0457(2) 0.9787(2) 0.2509(3) 0.0521(11) Uani 1 1 d . . . C7 C 0.0447(2) 0.9376(2) 0.3159(3) 0.0572(12) Uani 1 1 d . . . C8 C 0.0878(2) 0.9182(2) 0.3195(3) 0.0653(13) Uani 1 1 d . . . C9 C 0.1329(3) 0.9383(3) 0.2538(4) 0.0725(15) Uani 1 1 d . . . O5 O 0.2402(7) 0.9947(8) -0.0844(7) 0.312(8) Uani 1 1 d . . . C13 C 0.2416(9) 1.0319(10) -0.1444(12) 0.285(11) Uani 1 1 d . . . C12 C 0.2997(9) 1.0479(14) -0.1981(12) 0.313(14) Uani 1 1 d . . . C11 C 0.3336(9) 1.0289(12) -0.1600(13) 0.264(9) Uani 1 1 d . . . C10 C 0.3019(13) 0.9980(16) -0.0789(13) 0.41(2) Uani 1 1 d . . . O6 O 0.1490(11) 0.8574(12) 0.5831(12) 0.242(9) Uiso 0.50 1 d PD A 1 C14 C 0.1769(17) 0.9024(14) 0.655(2) 0.34(2) Uiso 0.50 1 d PD A 1 C15 C 0.1593(13) 0.8639(14) 0.7345(14) 0.391(16) Uiso 0.50 1 d PD A 1 C16 C 0.0678(15) 0.8337(19) 0.675(3) 0.297(19) Uiso 0.50 1 d PD A 1 C17 C 0.0918(10) 0.8032(9) 0.6189(15) 0.304(10) Uiso 0.50 1 d PD A 1 O6A O 0.1058(11) 0.8648(10) 0.6075(13) 0.228(8) Uiso 0.50 1 d PD B 2 C14A C 0.1330(10) 0.8989(8) 0.6946(13) 0.149(7) Uiso 0.50 1 d PD B 2 C15A C 0.1593(13) 0.8639(14) 0.7345(14) 0.391(16) Uiso 0.50 1 d PD B 2 C16A C 0.1257(16) 0.8015(13) 0.703(2) 0.231(12) Uiso 0.50 1 d PD B 2 C17A C 0.0918(10) 0.8032(9) 0.6189(15) 0.304(10) Uiso 0.50 1 d PD B 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.081(4) 0.189(6) 0.164(5) 0.016(5) 0.038(4) 0.046(4) O2 0.144(5) 0.192(6) 0.094(4) -0.007(4) 0.035(4) 0.090(5) O3 0.159(5) 0.091(4) 0.109(3) 0.016(3) 0.000(3) 0.076(4) O4 0.225(7) 0.161(5) 0.083(3) -0.021(3) -0.055(4) 0.137(5) Cl1 0.0829(10) 0.0850(10) 0.0722(9) 0.0224(7) 0.0160(7) 0.0427(8) Cl2 0.0804(10) 0.0754(9) 0.0647(8) 0.0130(6) 0.0156(6) 0.0424(8) Cl3 0.1030(13) 0.1454(17) 0.1295(15) 0.0112(12) 0.0091(10) 0.0954(13) C1 0.078(5) 0.129(6) 0.099(5) 0.022(5) 0.018(4) 0.057(5) C2 0.116(5) 0.104(5) 0.073(4) 0.005(4) -0.001(3) 0.079(5) C3 0.049(3) 0.049(3) 0.100(7) 0.000 0.000 0.0247(15) C4 0.059(3) 0.088(4) 0.076(4) 0.002(3) 0.008(3) 0.040(3) C5 0.057(3) 0.060(3) 0.061(3) 0.006(2) 0.001(2) 0.027(2) C6 0.048(3) 0.052(3) 0.054(3) 0.000(2) 0.001(2) 0.024(2) C7 0.060(3) 0.056(3) 0.058(3) 0.000(2) 0.006(2) 0.030(2) C8 0.071(3) 0.065(3) 0.069(3) -0.005(2) -0.007(3) 0.041(3) C9 0.067(3) 0.084(4) 0.083(4) -0.001(3) 0.000(3) 0.051(3) O5 0.391(17) 0.53(2) 0.194(9) 0.156(12) 0.167(10) 0.370(18) C13 0.292(19) 0.43(3) 0.242(16) 0.211(19) 0.090(15) 0.26(2) C12 0.196(15) 0.60(4) 0.208(15) 0.14(2) 0.070(12) 0.25(2) C11 0.207(16) 0.43(3) 0.201(16) 0.050(16) 0.043(13) 0.190(19) C10 0.51(4) 0.83(6) 0.230(18) 0.16(3) 0.14(2) 0.59(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.173(9) . ? O2 H2O 0.87(2) . ? O2 C1 1.270(10) . ? O3 C2 1.185(8) . ? O4 H4O 0.88(2) . ? O4 C2 1.293(8) . ? Cl1 C5 1.732(5) . ? Cl2 C7 1.725(5) . ? Cl3 C9 1.732(5) . ? C1 C4 1.538(9) . ? C2 C8 1.501(8) . ? C3 C6 1.478(4) 2_675 ? C3 C6 1.478(5) 3_465 ? C3 C6 1.477(4) . ? C4 C5 1.374(7) . ? C4 C9 1.389(8) . ? C5 C6 1.400(6) . ? C6 C7 1.410(6) . ? C7 C8 1.381(7) . ? C8 C9 1.391(7) . ? O5 C13 1.284(14) . ? O5 C10 1.50(2) . ? C13 C12 1.53(2) . ? C12 C11 1.29(2) . ? C11 C10 1.45(2) . ? O6 C14 1.46(2) . ? O6 C17 1.49(2) . ? C14 C15 1.46(3) . ? C16 C17 1.45(2) . ? O6A C14A 1.527(19) . ? 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 H2O O2 C1 108(8) . . ? H4O O4 C2 110(3) . . ? O1 C1 O2 125.7(7) . . ? O1 C1 C4 120.7(8) . . ? O2 C1 C4 113.6(7) . . ? O3 C2 O4 125.2(6) . . ? O3 C2 C8 123.7(6) . . ? O4 C2 C8 111.1(6) . . ? C6 C3 C6 119.96(3) 2_675 3_465 ? C6 C3 C6 119.96(3) 2_675 . ? C6 C3 C6 119.96(3) 3_465 . ? C5 C4 C9 119.0(5) . . ? C5 C4 C1 120.6(5) . . ? C9 C4 C1 120.4(5) . . ? C4 C5 C6 123.2(5) . . ? C4 C5 Cl1 117.0(4) . . ? C6 C5 Cl1 119.7(4) . . ? C5 C6 C7 115.3(4) . . ? C5 C6 C3 122.2(5) . . ? C7 C6 C3 122.5(5) . . ? C8 C7 C6 123.2(4) . . ? C8 C7 Cl2 116.5(4) . . ? C6 C7 Cl2 120.2(4) . . ? C7 C8 C9 118.4(5) . . ? C7 C8 C2 120.9(5) . . ? C9 C8 C2 120.7(5) . . ? C4 C9 C8 120.8(5) . . ? C4 C9 Cl3 120.3(4) . . ? C8 C9 Cl3 118.9(4) . . ? C13 O5 C10 110.1(15) . . ? O5 C13 C12 104.0(14) . . ? C11 C12 C13 112.1(15) . . ? C12 C11 C10 106.7(15) . . ? C11 C10 O5 104.6(14) . . ? C14 O6 C17 107.6(15) . . ? O6 C14 C15 103.5(19) . . ? C16 C17 O6 101.0(17) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 22.50 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.422 _refine_diff_density_min -0.370 _refine_diff_density_rms 0.060