# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Dr Ying-Chih Lin' _publ_contact_author_email yclin@ntu.edu.tw _publ_section_title ; One-Pot Synthesis of Substituted Benzene via Intermolecular [2+2+2] Cycloaddition Catalyzed by Air-Stable Ru(II)-Complex ; loop_ _publ_author_name 'Chung-Yeh Wu' 'Ying-Chih Lin' 'Pi-Tai Chou' 'Yu Wang' 'Yi-Hung Liu' # Attachment '- ic13526N4gs.cif' data_ic13526 _database_code_depnum_ccdc_archive 'CCDC 728460' #TrackingRef '- ic13526N4gs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H26 O8' _chemical_formula_weight 562.55 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.9034(6) _cell_length_b 11.1168(5) _cell_length_c 21.4260(9) _cell_angle_alpha 90.00 _cell_angle_beta 97.873(4) _cell_angle_gamma 90.00 _cell_volume 2808.5(2) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1809 _cell_measurement_theta_min 3.7445 _cell_measurement_theta_max 70.7174 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.330 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1176 _exptl_absorpt_coefficient_mu 0.784 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.66136 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Gemini A' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12030 _diffrn_reflns_av_R_equivalents 0.0578 _diffrn_reflns_av_sigmaI/netI 0.0631 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 4.03 _diffrn_reflns_theta_max 67.99 _reflns_number_total 5030 _reflns_number_gt 2234 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _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^)+(0.1000P)^2^+0.0000P] 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 0.0027(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5030 _refine_ls_number_parameters 380 _refine_ls_number_restraints 54 _refine_ls_R_factor_all 0.2295 _refine_ls_R_factor_gt 0.1341 _refine_ls_wR_factor_ref 0.3622 _refine_ls_wR_factor_gt 0.3213 _refine_ls_goodness_of_fit_ref 1.779 _refine_ls_restrained_S_all 1.818 _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 0.1471(5) 0.7774(5) 0.2385(2) 0.0916(18) Uani 1 1 d . . . O2 O 0.1852(5) 0.9691(5) 0.2176(2) 0.0866(16) Uani 1 1 d . . . O3 O 0.0220(5) 1.1931(6) 0.2477(3) 0.110(2) Uani 1 1 d . . . O4 O 0.0438(5) 1.0346(6) 0.3096(3) 0.114(2) Uani 1 1 d U . . O5 O -0.2240(5) 1.1584(6) 0.2606(3) 0.1009(19) Uani 1 1 d . . . O6 O -0.2605(6) 1.2202(5) 0.1621(3) 0.105(2) Uani 1 1 d . . . O7 O -0.3576(6) 1.0302(6) 0.0479(3) 0.123(3) Uani 1 1 d . . . O8 O -0.4080(8) 0.9986(7) 0.1452(4) 0.142(3) Uani 1 1 d . . . C1 C -0.0142(9) 0.7074(10) 0.1216(4) 0.100(3) Uani 1 1 d U . . C2 C 0.0661(9) 0.7179(11) 0.0876(4) 0.108(3) Uani 1 1 d U . . C3 C 0.1238(8) 0.8118(8) 0.0672(4) 0.085(2) Uani 1 1 d U . . H3A H 0.1036 0.8882 0.0821 0.102 Uiso 1 1 calc R . . C4 C 0.2060(10) 0.8147(12) 0.0290(5) 0.122(3) Uani 1 1 d U . . H4A H 0.2410 0.8865 0.0173 0.147 Uiso 1 1 calc R . . C5 C 0.2328(14) 0.7016(11) 0.0090(7) 0.167(6) Uani 1 1 d . . . H5A H 0.2907 0.6974 -0.0173 0.200 Uiso 1 1 calc R . . C6 C 0.1858(11) 0.5962(10) 0.0230(5) 0.116(4) Uani 1 1 d . . . H6A H 0.2093 0.5243 0.0046 0.139 Uiso 1 1 calc R . . C7 C 0.1038(12) 0.5898(10) 0.0634(6) 0.114(4) Uani 1 1 d . . . C8 C 0.0562(9) 0.4830(14) 0.0803(4) 0.116(4) Uani 1 1 d . . . H8A H 0.0796 0.4084 0.0648 0.139 Uiso 1 1 calc R . . C9 C -0.0270(9) 0.4869(10) 0.1208(5) 0.122(3) Uani 1 1 d U . . H9A H -0.0601 0.4152 0.1341 0.146 Uiso 1 1 calc R . . C10 C -0.0606(8) 0.6030(7) 0.1414(4) 0.087(2) Uani 1 1 d U . . H10A H -0.1159 0.6077 0.1693 0.104 Uiso 1 1 calc R . . C11 C -0.2484(8) 0.7845(7) 0.0677(3) 0.080(2) Uani 1 1 d . . . C12 C -0.2328(7) 0.7858(6) 0.0052(3) 0.069(2) Uani 1 1 d . . . C13 C -0.1382(7) 0.8584(6) -0.0188(3) 0.071(2) Uani 1 1 d . . . H13A H -0.0860 0.9047 0.0090 0.085 Uiso 1 1 calc R . . C14 C -0.1326(7) 0.8535(7) -0.0824(3) 0.076(2) Uani 1 1 d . . . H14A H -0.0728 0.8957 -0.0979 0.092 Uiso 1 1 calc R . . C15 C -0.2073(9) 0.7916(8) -0.1246(4) 0.094(3) Uani 1 1 d . . . H15A H -0.2008 0.7940 -0.1683 0.113 Uiso 1 1 calc R . . C16 C -0.2870(8) 0.7299(8) -0.1045(4) 0.083(2) Uani 1 1 d . . . H16A H -0.3364 0.6848 -0.1344 0.099 Uiso 1 1 calc R . . C17 C -0.3051(6) 0.7254(6) -0.0406(3) 0.0635(19) Uani 1 1 d . . . C18 C -0.3969(8) 0.6537(7) -0.0208(4) 0.092(3) Uani 1 1 d . . . H18A H -0.4479 0.6102 -0.0505 0.110 Uiso 1 1 calc R . . C19 C -0.4069(7) 0.6516(7) 0.0440(4) 0.078(2) Uani 1 1 d . . . H19A H -0.4646 0.6060 0.0595 0.093 Uiso 1 1 calc R . . C20 C -0.3295(8) 0.7185(7) 0.0845(4) 0.080(2) Uani 1 1 d . . . H20A H -0.3364 0.7158 0.1281 0.096 Uiso 1 1 calc R . . C21 C -0.1722(7) 0.8642(7) 0.1153(3) 0.090(3) Uani 1 1 d . . . C22 C -0.2201(7) 0.9681(7) 0.1343(3) 0.082(2) Uani 1 1 d . . . C23 C -0.1611(7) 1.0409(6) 0.1808(3) 0.070(2) Uani 1 1 d . . . C24 C -0.0515(6) 1.0093(6) 0.2078(3) 0.0661(19) Uani 1 1 d . . . C25 C 0.0007(7) 0.9057(6) 0.1879(3) 0.070(2) Uani 1 1 d . . . C26 C -0.0610(8) 0.8308(7) 0.1421(3) 0.088(3) Uani 1 1 d . . . C27 C 0.1183(7) 0.8734(8) 0.2174(3) 0.075(2) Uani 1 1 d . . . C28 C 0.2968(8) 0.9569(10) 0.2546(5) 0.126(4) Uani 1 1 d . . . H28A H 0.3398 1.0314 0.2519 0.189 Uiso 1 1 calc R . . H28B H 0.3375 0.8899 0.2381 0.189 Uiso 1 1 calc R . . H28C H 0.2881 0.9410 0.2987 0.189 Uiso 1 1 calc R . . C29 C 0.0071(9) 1.0855(11) 0.2574(5) 0.111(3) Uani 1 1 d U . . C30 C 0.1255(11) 1.1334(13) 0.3451(5) 0.173(5) Uani 1 1 d U . . H30A H 0.1591 1.1023 0.3862 0.260 Uiso 1 1 calc R . . H30B H 0.0819 1.2063 0.3510 0.260 Uiso 1 1 calc R . . H30C H 0.1858 1.1526 0.3198 0.260 Uiso 1 1 calc R . . C31 C -0.2164(7) 1.1455(7) 0.2058(4) 0.075(2) Uani 1 1 d . . . C32 C -0.3264(12) 1.3196(10) 0.1831(5) 0.164(5) Uani 1 1 d . . . H32A H -0.3553 1.3699 0.1468 0.245 Uiso 1 1 calc R . . H32B H -0.2778 1.3681 0.2141 0.245 Uiso 1 1 calc R . . H32C H -0.3902 1.2875 0.2024 0.245 Uiso 1 1 calc R . . C33 C -0.3409(9) 1.0047(7) 0.1032(5) 0.095(3) Uani 1 1 d . . . C34 C -0.5264(10) 1.0303(15) 0.1084(8) 0.216(8) Uani 1 1 d . . . H34A H -0.5835 1.0283 0.1373 0.324 Uiso 1 1 calc R . . H34B H -0.5463 0.9716 0.0746 0.324 Uiso 1 1 calc R . . H34C H -0.5239 1.1110 0.0902 0.324 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 0.098(4) 0.082(4) 0.081(3) 0.010(3) -0.036(3) 0.002(3) O2 0.079(4) 0.091(4) 0.085(3) 0.019(3) -0.006(3) 0.010(3) O3 0.098(5) 0.088(4) 0.141(5) -0.046(4) 0.008(4) -0.015(4) O4 0.112(4) 0.139(5) 0.080(3) -0.044(3) -0.021(3) -0.001(4) O5 0.111(5) 0.117(5) 0.075(4) -0.026(3) 0.017(3) 0.010(4) O6 0.144(6) 0.080(4) 0.091(4) -0.011(3) 0.020(4) 0.040(4) O7 0.135(6) 0.103(4) 0.114(5) -0.020(4) -0.045(4) 0.045(4) O8 0.134(7) 0.129(6) 0.164(7) 0.006(5) 0.022(6) 0.041(6) C1 0.091(6) 0.124(6) 0.072(4) 0.013(5) -0.031(4) -0.004(5) C2 0.089(6) 0.147(7) 0.079(5) 0.022(5) -0.018(4) 0.000(5) C3 0.088(6) 0.098(5) 0.066(4) 0.012(4) -0.001(4) 0.011(5) C4 0.120(7) 0.139(6) 0.103(6) 0.013(5) 0.002(5) 0.004(6) C5 0.204(14) 0.091(8) 0.188(13) 0.015(9) -0.036(11) 0.016(9) C6 0.137(10) 0.088(7) 0.119(8) -0.012(6) 0.006(7) 0.046(7) C7 0.126(10) 0.100(8) 0.099(7) -0.027(6) -0.046(7) 0.066(8) C8 0.093(8) 0.186(12) 0.066(5) -0.005(7) 0.004(5) 0.051(9) C9 0.119(6) 0.118(6) 0.112(5) 0.005(5) -0.043(5) 0.011(5) C10 0.091(5) 0.076(4) 0.083(4) -0.007(4) -0.026(4) 0.019(4) C11 0.098(7) 0.072(5) 0.068(5) -0.002(4) -0.001(4) 0.024(5) C12 0.095(6) 0.052(4) 0.053(4) -0.002(3) -0.014(4) 0.026(4) C13 0.084(6) 0.055(4) 0.067(4) -0.002(3) -0.011(4) 0.014(4) C14 0.111(7) 0.070(4) 0.050(4) 0.002(3) 0.018(4) 0.017(5) C15 0.125(8) 0.083(6) 0.070(5) 0.002(4) -0.004(5) -0.001(6) C16 0.096(7) 0.082(6) 0.067(5) 0.004(4) 0.004(4) 0.030(5) C17 0.072(5) 0.058(4) 0.056(4) -0.001(3) -0.011(3) 0.009(4) C18 0.093(7) 0.067(5) 0.107(7) -0.020(5) -0.014(5) 0.019(5) C19 0.080(6) 0.068(5) 0.086(5) 0.010(4) 0.014(4) 0.000(4) C20 0.094(6) 0.073(5) 0.069(5) -0.001(4) 0.002(4) 0.008(5) C21 0.100(7) 0.084(5) 0.074(5) -0.017(4) -0.026(4) 0.030(5) C22 0.091(6) 0.070(5) 0.075(5) -0.020(4) -0.016(4) 0.019(5) C23 0.090(6) 0.066(4) 0.051(4) -0.006(3) 0.000(4) 0.010(4) C24 0.089(6) 0.066(4) 0.042(3) 0.002(3) 0.005(3) -0.006(4) C25 0.084(5) 0.071(4) 0.048(3) -0.006(3) -0.012(3) 0.017(4) C26 0.110(7) 0.085(5) 0.064(4) -0.013(4) -0.013(4) 0.043(5) C27 0.086(6) 0.086(6) 0.050(4) -0.008(4) -0.003(4) 0.008(5) C28 0.084(7) 0.129(8) 0.157(9) 0.043(7) -0.017(6) -0.014(6) C29 0.101(6) 0.128(7) 0.098(6) -0.045(6) -0.009(5) -0.002(6) C30 0.172(9) 0.233(11) 0.107(7) -0.050(7) -0.005(7) -0.047(9) C31 0.076(6) 0.078(5) 0.072(5) -0.014(4) 0.014(4) 0.003(4) C32 0.223(14) 0.120(8) 0.143(9) -0.052(7) 0.009(9) 0.095(9) C33 0.105(8) 0.060(5) 0.110(7) -0.022(5) -0.027(6) 0.025(5) C34 0.098(9) 0.248(17) 0.287(18) 0.097(15) -0.026(10) 0.072(11) _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 C27 1.192(8) . ? O2 C27 1.329(9) . ? O2 C28 1.457(9) . ? O3 C29 1.231(12) . ? O4 C29 1.276(12) . ? O4 C30 1.590(12) . ? O5 C31 1.198(8) . ? O6 C31 1.307(9) . ? O6 C32 1.461(10) . ? O7 C33 1.208(11) . ? O8 C33 1.284(12) . ? O8 C34 1.558(12) . ? C1 C2 1.284(13) . ? C1 C10 1.378(12) . ? C1 C26 1.567(13) . ? C2 C3 1.354(13) . ? C2 C7 1.601(14) . ? C3 C4 1.360(13) . ? C4 C5 1.379(16) . ? C5 C6 1.349(16) . ? C6 C7 1.392(16) . ? C7 C8 1.385(15) . ? C8 C9 1.403(13) . ? C9 C10 1.438(13) . ? C11 C20 1.302(11) . ? C11 C12 1.377(10) . ? C11 C21 1.547(11) . ? C12 C17 1.387(9) . ? C12 C13 1.531(10) . ? C13 C14 1.375(9) . ? C14 C15 1.365(11) . ? C15 C16 1.292(11) . ? C16 C17 1.416(10) . ? C17 C18 1.461(11) . ? C18 C19 1.411(11) . ? C19 C20 1.392(10) . ? C21 C22 1.374(10) . ? C21 C26 1.419(10) . ? C22 C23 1.397(9) . ? C22 C33 1.554(11) . ? C23 C24 1.397(10) . ? C23 C31 1.472(10) . ? C24 C25 1.403(9) . ? C24 C29 1.460(11) . ? C25 C26 1.413(10) . ? C25 C27 1.498(10) . ? 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 C27 O2 C28 115.4(6) . . ? C29 O4 C30 103.0(9) . . ? C31 O6 C32 116.2(7) . . ? C33 O8 C34 103.9(9) . . ? C2 C1 C10 127.8(12) . . ? C2 C1 C26 113.6(10) . . ? C10 C1 C26 118.6(10) . . ? C1 C2 C3 134.7(12) . . ? C1 C2 C7 111.5(12) . . ? C3 C2 C7 113.9(11) . . ? C2 C3 C4 130.6(11) . . ? C3 C4 C5 112.4(13) . . ? C6 C5 C4 127.0(16) . . ? C5 C6 C7 122.0(12) . . ? C8 C7 C6 123.6(10) . . ? C8 C7 C2 122.3(14) . . ? C6 C7 C2 114.0(12) . . ? C7 C8 C9 119.0(14) . . ? C8 C9 C10 117.8(11) . . ? C1 C10 C9 121.4(10) . . ? C20 C11 C12 118.6(8) . . ? C20 C11 C21 122.0(8) . . ? C12 C11 C21 119.4(9) . . ? C11 C12 C17 122.0(8) . . ? C11 C12 C13 122.3(7) . . ? C17 C12 C13 115.6(6) . . ? C14 C13 C12 116.7(7) . . ? C15 C14 C13 124.2(9) . . ? C16 C15 C14 119.2(9) . . ? C15 C16 C17 123.8(9) . . ? C12 C17 C16 120.4(8) . . ? C12 C17 C18 118.4(7) . . ? C16 C17 C18 121.2(7) . . ? C19 C18 C17 117.5(7) . . ? C20 C19 C18 117.9(8) . . ? C11 C20 C19 125.5(8) . . ? C22 C21 C26 120.1(7) . . ? C22 C21 C11 116.6(7) . . ? C26 C21 C11 123.2(7) . . ? C21 C22 C23 120.7(7) . . ? C21 C22 C33 119.4(6) . . ? C23 C22 C33 120.0(7) . . ? C22 C23 C24 120.0(7) . . ? C22 C23 C31 120.7(7) . . ? C24 C23 C31 119.1(6) . . ? C23 C24 C25 120.5(6) . . ? C23 C24 C29 118.7(7) . . ? C25 C24 C29 120.7(7) . . ? C24 C25 C26 119.0(7) . . ? C24 C25 C27 119.7(6) . . ? C26 C25 C27 121.2(7) . . ? C25 C26 C21 119.6(7) . . ? C25 C26 C1 122.7(7) . . ? C21 C26 C1 117.6(7) . . ? O1 C27 O2 125.0(7) . . ? O1 C27 C25 125.4(8) . . ? O2 C27 C25 109.6(7) . . ? O3 C29 O4 122.6(9) . . ? O3 C29 C24 120.5(9) . . ? O4 C29 C24 116.9(10) . . ? O5 C31 O6 123.3(7) . . ? O5 C31 C23 123.3(8) . . ? O6 C31 C23 113.4(6) . . ? O7 C33 O8 131.6(10) . . ? O7 C33 C22 120.1(11) . . ? O8 C33 C22 108.3(9) . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 67.99 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 1.020 _refine_diff_density_min -0.430 _refine_diff_density_rms 0.087 # Attachment '- ic13524N7.cif' data_ic13524 _database_code_depnum_ccdc_archive 'CCDC 728461' #TrackingRef '- ic13524N7.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H16 O8 S2' _chemical_formula_weight 472.47 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.0718(3) _cell_length_b 19.0514(9) _cell_length_c 11.6545(4) _cell_angle_alpha 90.00 _cell_angle_beta 91.567(4) _cell_angle_gamma 90.00 _cell_volume 2013.50(14) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2896 _cell_measurement_theta_min 4.4465 _cell_measurement_theta_max 70.2321 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.559 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 976 _exptl_absorpt_coefficient_mu 2.853 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.79218 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Gemini A' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11482 _diffrn_reflns_av_R_equivalents 0.0524 _diffrn_reflns_av_sigmaI/netI 0.0407 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 4.45 _diffrn_reflns_theta_max 67.99 _reflns_number_total 3633 _reflns_number_gt 2685 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _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^)+(0.1000P)^2^+0.0000P] 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 3633 _refine_ls_number_parameters 289 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0882 _refine_ls_R_factor_gt 0.0668 _refine_ls_wR_factor_ref 0.2088 _refine_ls_wR_factor_gt 0.1909 _refine_ls_goodness_of_fit_ref 1.434 _refine_ls_restrained_S_all 1.434 _refine_ls_shift/su_max 0.015 _refine_ls_shift/su_mean 0.002 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 S1 S 0.47107(12) 0.62655(6) 0.54217(8) 0.0401(3) Uani 1 1 d . . . S2 S 0.03740(12) 0.37509(6) 0.56864(9) 0.0422(3) Uani 1 1 d . . . O1 O 0.3024(3) 0.68395(16) 0.3267(2) 0.0439(7) Uani 1 1 d . . . O2 O 0.5085(3) 0.63110(16) 0.2689(3) 0.0455(7) Uani 1 1 d . . . O3 O 0.3125(4) 0.51804(18) 0.0101(2) 0.0530(8) Uani 1 1 d . . . O4 O 0.2725(4) 0.62336(17) 0.0889(2) 0.0492(8) Uani 1 1 d . . . O5 O 0.0467(5) 0.4266(3) 0.0508(3) 0.0836(14) Uani 1 1 d . . . O6 O 0.2439(6) 0.36350(19) 0.0986(3) 0.0745(13) Uani 1 1 d . . . O7 O 0.1726(4) 0.30582(17) 0.3417(3) 0.0512(8) Uani 1 1 d . . . O8 O -0.0430(3) 0.35812(16) 0.3019(3) 0.0487(8) Uani 1 1 d . . . C1 C 0.4811(5) 0.6146(2) 0.6884(4) 0.0418(10) Uani 1 1 d . . . H1A H 0.5433 0.6414 0.7385 0.050 Uiso 1 1 calc R . . C2 C 0.3918(5) 0.5631(2) 0.7244(3) 0.0402(9) Uani 1 1 d . . . H2A H 0.3824 0.5501 0.8026 0.048 Uiso 1 1 calc R . . C3 C 0.3125(4) 0.5304(2) 0.6309(3) 0.0359(9) Uani 1 1 d . . . C4 C 0.2112(4) 0.4743(2) 0.6383(3) 0.0370(9) Uani 1 1 d . . . C5 C 0.1477(5) 0.4453(2) 0.7386(3) 0.0409(10) Uani 1 1 d . . . H5A H 0.1694 0.4612 0.8144 0.049 Uiso 1 1 calc R . . C6 C 0.0533(5) 0.3925(2) 0.7129(4) 0.0438(10) Uani 1 1 d . . . H6A H 0.0007 0.3675 0.7692 0.053 Uiso 1 1 calc R . . C7 C 0.1605(4) 0.4417(2) 0.5369(3) 0.0365(9) Uani 1 1 d . . . C8 C 0.2020(4) 0.4668(2) 0.4261(3) 0.0340(8) Uani 1 1 d . . . C9 C 0.1651(4) 0.4304(2) 0.3222(3) 0.0358(9) Uani 1 1 d . . . C10 C 0.1964(5) 0.4581(2) 0.2157(3) 0.0381(9) Uani 1 1 d . . . C11 C 0.2620(5) 0.5245(2) 0.2088(3) 0.0392(9) Uani 1 1 d . . . C12 C 0.3068(4) 0.5590(2) 0.3093(3) 0.0350(9) Uani 1 1 d . . . C13 C 0.2850(4) 0.5289(2) 0.4195(3) 0.0331(8) Uani 1 1 d . . . C14 C 0.3440(4) 0.5589(2) 0.5252(3) 0.0338(8) Uani 1 1 d . . . C15 C 0.3697(5) 0.6315(2) 0.3013(3) 0.0361(9) Uani 1 1 d . . . C16 C 0.5767(6) 0.7001(3) 0.2623(5) 0.0626(13) Uani 1 1 d . . . H16A H 0.6788 0.6950 0.2380 0.094 Uiso 1 1 calc R . . H16B H 0.5759 0.7226 0.3379 0.094 Uiso 1 1 calc R . . H16C H 0.5215 0.7291 0.2065 0.094 Uiso 1 1 calc R . . C17 C 0.2866(5) 0.5533(2) 0.0924(3) 0.0407(10) Uani 1 1 d . . . C18 C 0.3011(7) 0.6553(3) -0.0207(4) 0.0611(14) Uani 1 1 d . . . H18A H 0.2881 0.7062 -0.0151 0.092 Uiso 1 1 calc R . . H18B H 0.2322 0.6365 -0.0791 0.092 Uiso 1 1 calc R . . H18C H 0.4025 0.6449 -0.0422 0.092 Uiso 1 1 calc R . . C19 C 0.1520(6) 0.4164(3) 0.1106(4) 0.0504(12) Uani 1 1 d . . . C20 C 0.2043(12) 0.3157(4) 0.0050(5) 0.108(3) Uani 1 1 d . . . H20B H 0.2776 0.2780 0.0017 0.163 Uiso 1 1 calc R . . H20C H 0.2018 0.3415 -0.0678 0.163 Uiso 1 1 calc R . . H20D H 0.1069 0.2954 0.0181 0.163 Uiso 1 1 calc R . . C21 C 0.1012(5) 0.3579(2) 0.3240(3) 0.0372(9) Uani 1 1 d . . . C22 C -0.1135(6) 0.2902(3) 0.3011(5) 0.0647(15) Uani 1 1 d . . . H22B H -0.2191 0.2958 0.2839 0.097 Uiso 1 1 calc R . . H22C H -0.0994 0.2680 0.3765 0.097 Uiso 1 1 calc R . . H22D H -0.0696 0.2605 0.2423 0.097 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 S1 0.0472(6) 0.0367(6) 0.0361(5) -0.0017(4) -0.0012(4) -0.0036(4) S2 0.0462(6) 0.0420(6) 0.0387(6) 0.0037(4) 0.0042(4) -0.0042(5) O1 0.0566(18) 0.0351(17) 0.0398(15) 0.0030(12) 0.0006(12) 0.0067(14) O2 0.0461(17) 0.0342(16) 0.0565(18) 0.0076(13) 0.0070(13) -0.0047(13) O3 0.079(2) 0.0432(19) 0.0375(16) 0.0004(14) 0.0095(14) 0.0034(16) O4 0.078(2) 0.0388(17) 0.0310(15) 0.0041(12) 0.0006(14) 0.0003(15) O5 0.069(3) 0.130(4) 0.051(2) -0.023(2) -0.0131(18) -0.010(3) O6 0.140(4) 0.043(2) 0.0391(18) -0.0104(15) -0.024(2) 0.017(2) O7 0.0493(17) 0.0353(18) 0.069(2) 0.0120(15) 0.0031(14) 0.0037(14) O8 0.0443(17) 0.0347(17) 0.067(2) 0.0033(14) -0.0082(14) -0.0035(13) C1 0.049(2) 0.038(2) 0.038(2) -0.0038(17) -0.0045(17) 0.0048(19) C2 0.051(2) 0.036(2) 0.033(2) -0.0015(17) -0.0014(16) 0.0039(19) C3 0.043(2) 0.032(2) 0.0325(19) -0.0040(15) 0.0013(15) 0.0116(17) C4 0.042(2) 0.035(2) 0.034(2) 0.0033(16) 0.0033(15) 0.0053(17) C5 0.052(2) 0.040(2) 0.0306(19) 0.0033(16) 0.0052(16) 0.0077(19) C6 0.045(2) 0.044(3) 0.043(2) 0.0091(18) 0.0091(17) 0.0025(19) C7 0.040(2) 0.035(2) 0.035(2) 0.0003(16) 0.0027(15) 0.0074(17) C8 0.0355(19) 0.035(2) 0.0318(19) -0.0008(15) 0.0010(14) 0.0053(16) C9 0.036(2) 0.038(2) 0.0336(19) 0.0021(16) -0.0038(14) 0.0058(16) C10 0.043(2) 0.039(2) 0.0317(19) 0.0011(16) -0.0006(15) 0.0012(18) C11 0.044(2) 0.041(2) 0.032(2) 0.0062(17) -0.0012(16) -0.0007(18) C12 0.036(2) 0.034(2) 0.035(2) 0.0010(16) 0.0033(15) 0.0062(16) C13 0.0348(19) 0.031(2) 0.0333(19) 0.0014(15) 0.0009(14) 0.0037(16) C14 0.037(2) 0.029(2) 0.036(2) 0.0028(15) 0.0042(15) 0.0026(15) C15 0.046(2) 0.033(2) 0.0301(18) 0.0055(16) -0.0010(15) 0.0034(18) C16 0.059(3) 0.042(3) 0.087(4) 0.008(3) 0.010(3) -0.009(2) C17 0.050(2) 0.041(2) 0.031(2) -0.0003(17) 0.0013(16) 0.0021(18) C18 0.103(4) 0.044(3) 0.036(2) 0.008(2) 0.009(2) 0.002(3) C19 0.065(3) 0.053(3) 0.033(2) 0.0021(19) -0.004(2) -0.008(2) C20 0.227(10) 0.054(4) 0.043(3) -0.018(3) -0.032(4) 0.005(5) C21 0.046(2) 0.035(2) 0.0311(19) 0.0037(16) 0.0005(15) -0.0021(18) C22 0.059(3) 0.043(3) 0.091(4) 0.006(3) -0.015(3) -0.015(2) _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 S1 C1 1.719(4) . ? S1 C14 1.737(4) . ? S2 C6 1.716(4) . ? S2 C7 1.737(4) . ? O1 C15 1.211(5) . ? O2 C15 1.324(5) . ? O2 C16 1.456(6) . ? O3 C17 1.200(5) . ? O4 C17 1.341(5) . ? O4 C18 1.444(6) . ? O5 C19 1.183(6) . ? O6 C19 1.318(7) . ? O6 C20 1.459(6) . ? O7 C21 1.200(5) . ? O8 C21 1.326(5) . ? O8 C22 1.444(6) . ? C1 C2 1.347(7) . ? C2 C3 1.433(6) . ? C3 C14 1.383(6) . ? C3 C4 1.414(6) . ? C4 C7 1.401(6) . ? C4 C5 1.429(6) . ? C5 C6 1.349(6) . ? C7 C8 1.436(6) . ? C8 C13 1.406(6) . ? C8 C9 1.428(6) . ? C9 C10 1.385(6) . ? C9 C21 1.498(6) . ? C10 C11 1.400(6) . ? C10 C19 1.506(6) . ? C11 C12 1.394(6) . ? C11 C17 1.486(6) . ? C12 C13 1.426(5) . ? C12 C15 1.499(6) . ? C13 C14 1.447(5) . ? 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 C1 S1 C14 91.8(2) . . ? C6 S2 C7 91.7(2) . . ? C15 O2 C16 114.7(4) . . ? C17 O4 C18 115.3(4) . . ? C19 O6 C20 114.4(5) . . ? C21 O8 C22 115.7(4) . . ? C2 C1 S1 112.9(3) . . ? C1 C2 C3 111.9(4) . . ? C14 C3 C4 120.1(3) . . ? C14 C3 C2 113.3(4) . . ? C4 C3 C2 126.6(4) . . ? C7 C4 C3 118.8(4) . . ? C7 C4 C5 112.9(4) . . ? C3 C4 C5 128.3(4) . . ? C6 C5 C4 111.9(4) . . ? C5 C6 S2 113.4(3) . . ? C4 C7 C8 121.5(4) . . ? C4 C7 S2 110.0(3) . . ? C8 C7 S2 128.3(3) . . ? C13 C8 C9 118.4(3) . . ? C13 C8 C7 118.9(3) . . ? C9 C8 C7 122.7(4) . . ? C10 C9 C8 121.7(4) . . ? C10 C9 C21 117.0(3) . . ? C8 C9 C21 121.1(4) . . ? C9 C10 C11 119.6(4) . . ? C9 C10 C19 118.1(4) . . ? C11 C10 C19 122.3(4) . . ? C12 C11 C10 119.5(4) . . ? C12 C11 C17 123.0(4) . . ? C10 C11 C17 117.4(4) . . ? C11 C12 C13 121.5(4) . . ? C11 C12 C15 119.1(3) . . ? C13 C12 C15 119.3(3) . . ? C8 C13 C12 118.4(3) . . ? C8 C13 C14 118.1(3) . . ? C12 C13 C14 123.4(4) . . ? C3 C14 C13 121.5(4) . . ? C3 C14 S1 110.1(3) . . ? C13 C14 S1 128.2(3) . . ? O1 C15 O2 124.4(4) . . ? O1 C15 C12 123.3(4) . . ? O2 C15 C12 112.2(3) . . ? O3 C17 O4 123.6(4) . . ? O3 C17 C11 124.1(4) . . ? O4 C17 C11 112.3(4) . . ? O5 C19 O6 124.5(5) . . ? O5 C19 C10 125.9(5) . . ? O6 C19 C10 109.5(4) . . ? O7 C21 O8 124.1(4) . . ? O7 C21 C9 123.9(4) . . ? O8 C21 C9 112.0(4) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 67.99 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.688 _refine_diff_density_min -0.506 _refine_diff_density_rms 0.097 # Attachment '- ic13734N4ga.cif' data_ic13734 _database_code_depnum_ccdc_archive 'CCDC 728462' #TrackingRef '- ic13734N4ga.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H26 O8' _chemical_formula_weight 562.55 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.79120(10) _cell_length_b 13.56520(10) _cell_length_c 24.5222(2) _cell_angle_alpha 90.00 _cell_angle_beta 98.6200(10) _cell_angle_gamma 90.00 _cell_volume 2891.35(5) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 17758 _cell_measurement_theta_min 3.2602 _cell_measurement_theta_max 77.5905 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.292 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1176 _exptl_absorpt_coefficient_mu 0.762 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.92376 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET) (compiled Feb 27 2009,15:38:38) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Gemini A' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23056 _diffrn_reflns_av_R_equivalents 0.0174 _diffrn_reflns_av_sigmaI/netI 0.0101 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 3.65 _diffrn_reflns_theta_max 67.99 _reflns_number_total 5278 _reflns_number_gt 4723 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET) (compiled Feb 27 2009,15:38:38) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET) (compiled Feb 27 2009,15:38:38) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET) (compiled Feb 27 2009,15:38:38) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _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^)+(0.1000P)^2^+0.0000P] 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 0.0033(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5278 _refine_ls_number_parameters 380 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0441 _refine_ls_R_factor_gt 0.0405 _refine_ls_wR_factor_ref 0.1623 _refine_ls_wR_factor_gt 0.1572 _refine_ls_goodness_of_fit_ref 1.454 _refine_ls_restrained_S_all 1.454 _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 0.63804(13) 0.51056(8) 0.06577(5) 0.0633(3) Uani 1 1 d . . . O2 O 0.50227(11) 0.38301(7) 0.08977(4) 0.0498(3) Uani 1 1 d . . . O3 O 0.86820(16) 0.55605(10) 0.21753(6) 0.0815(4) Uani 1 1 d . . . O4 O 0.63497(13) 0.49406(10) 0.19018(5) 0.0683(4) Uani 1 1 d . . . O5 O 0.99638(16) 0.37842(13) 0.28637(5) 0.0827(4) Uani 1 1 d . . . O6 O 1.19837(13) 0.42038(8) 0.24541(4) 0.0594(3) Uani 1 1 d . . . O7 O 1.18394(13) 0.18669(9) 0.23157(5) 0.0632(3) Uani 1 1 d . . . O8 O 1.30288(11) 0.25382(9) 0.16653(4) 0.0580(3) Uani 1 1 d . . . C1 C 0.82815(13) 0.29778(9) 0.08653(5) 0.0366(3) Uani 1 1 d . . . C2 C 0.77026(14) 0.37624(9) 0.11389(5) 0.0374(3) Uani 1 1 d . . . C3 C 0.84412(14) 0.40857(9) 0.16521(5) 0.0397(3) Uani 1 1 d . . . C4 C 0.97994(14) 0.36284(9) 0.18908(5) 0.0397(3) Uani 1 1 d . . . C5 C 1.03917(13) 0.28503(9) 0.16203(5) 0.0372(3) Uani 1 1 d . . . C6 C 0.96303(14) 0.24969(9) 0.11152(5) 0.0367(3) Uani 1 1 d . . . C7 C 0.74898(14) 0.26786(9) 0.03028(5) 0.0377(3) Uani 1 1 d . . . C8 C 0.61955(16) 0.21024(11) 0.02468(5) 0.0492(3) Uani 1 1 d . . . H8A H 0.5834 0.1869 0.0560 0.059 Uiso 1 1 calc R . . C9 C 0.54047(17) 0.18591(13) -0.02781(6) 0.0581(4) Uani 1 1 d . . . H9A H 0.4534 0.1462 -0.0308 0.070 Uiso 1 1 calc R . . C10 C 0.58968(17) 0.21968(11) -0.07396(6) 0.0523(3) Uani 1 1 d . . . H10A H 0.5358 0.2034 -0.1084 0.063 Uiso 1 1 calc R . . C11 C 0.72217(15) 0.27950(9) -0.07048(5) 0.0418(3) Uani 1 1 d . . . C12 C 0.77744(19) 0.31455(11) -0.11848(5) 0.0525(4) Uani 1 1 d . . . H12A H 0.7245 0.2986 -0.1531 0.063 Uiso 1 1 calc R . . C13 C 0.9064(2) 0.37101(12) -0.11471(7) 0.0600(4) Uani 1 1 d . . . H13A H 0.9412 0.3933 -0.1465 0.072 Uiso 1 1 calc R . . C14 C 0.9870(2) 0.39559(11) -0.06267(7) 0.0578(4) Uani 1 1 d . . . H14A H 1.0753 0.4341 -0.0603 0.069 Uiso 1 1 calc R . . C15 C 0.93739(16) 0.36377(9) -0.01567(6) 0.0454(3) Uani 1 1 d . . . H15A H 0.9919 0.3815 0.0184 0.055 Uiso 1 1 calc R . . C16 C 0.80439(14) 0.30419(8) -0.01769(5) 0.0366(3) Uani 1 1 d . . . C17 C 1.01738(14) 0.15599(9) 0.08892(5) 0.0377(3) Uani 1 1 d . . . C18 C 1.14124(16) 0.15385(10) 0.06085(5) 0.0459(3) Uani 1 1 d . . . H18A H 1.1881 0.2126 0.0530 0.055 Uiso 1 1 calc R . . C19 C 1.19809(18) 0.06380(11) 0.04375(6) 0.0538(4) Uani 1 1 d . . . H19A H 1.2837 0.0635 0.0256 0.065 Uiso 1 1 calc R . . C20 C 1.12910(18) -0.02263(11) 0.05355(6) 0.0524(4) Uani 1 1 d . . . H20A H 1.1664 -0.0814 0.0412 0.063 Uiso 1 1 calc R . . C21 C 1.00134(16) -0.02412(10) 0.08222(5) 0.0455(3) Uani 1 1 d . . . C22 C 0.9294(2) -0.11361(11) 0.09359(7) 0.0605(4) Uani 1 1 d . . . H22A H 0.9646 -0.1727 0.0809 0.073 Uiso 1 1 calc R . . C23 C 0.8100(2) -0.11446(13) 0.12271(8) 0.0697(5) Uani 1 1 d . . . H23A H 0.7645 -0.1739 0.1300 0.084 Uiso 1 1 calc R . . C24 C 0.7550(2) -0.02591(15) 0.14178(8) 0.0689(5) Uani 1 1 d . . . H24A H 0.6735 -0.0270 0.1619 0.083 Uiso 1 1 calc R . . C25 C 0.81991(17) 0.06181(11) 0.13104(6) 0.0525(3) Uani 1 1 d . . . H25A H 0.7817 0.1199 0.1439 0.063 Uiso 1 1 calc R . . C26 C 0.94463(14) 0.06592(9) 0.10070(5) 0.0398(3) Uani 1 1 d . . . C27 C 0.62997(14) 0.43168(9) 0.08663(5) 0.0394(3) Uani 1 1 d . . . C28 C 0.36038(17) 0.43180(14) 0.06730(8) 0.0659(4) Uani 1 1 d . . . H28A H 0.2748 0.3901 0.0717 0.099 Uiso 1 1 calc R . . H28B H 0.3602 0.4449 0.0288 0.099 Uiso 1 1 calc R . . H28C H 0.3519 0.4928 0.0865 0.099 Uiso 1 1 calc R . . C29 C 0.78659(16) 0.49500(10) 0.19397(5) 0.0480(3) Uani 1 1 d . . . C30 C 0.5650(3) 0.5804(2) 0.21039(9) 0.1003(9) Uani 1 1 d . . . H30A H 0.4554 0.5720 0.2057 0.150 Uiso 1 1 calc R . . H30B H 0.5896 0.6373 0.1901 0.150 Uiso 1 1 calc R . . H30C H 0.6035 0.5894 0.2488 0.150 Uiso 1 1 calc R . . C31 C 1.05601(17) 0.38986(11) 0.24610(5) 0.0485(3) Uani 1 1 d . . . C32 C 1.2878(3) 0.43773(16) 0.29929(8) 0.0829(6) Uani 1 1 d . . . H32A H 1.3892 0.4596 0.2949 0.124 Uiso 1 1 calc R . . H32B H 1.2951 0.3777 0.3203 0.124 Uiso 1 1 calc R . . H32C H 1.2384 0.4874 0.3183 0.124 Uiso 1 1 calc R . . C33 C 1.18214(14) 0.23459(9) 0.19084(5) 0.0400(3) Uani 1 1 d . . . C34 C 1.4480(2) 0.2127(2) 0.19226(10) 0.0891(7) Uani 1 1 d . . . H34A H 1.5276 0.2311 0.1714 0.134 Uiso 1 1 calc R . . H34B H 1.4402 0.1422 0.1933 0.134 Uiso 1 1 calc R . . H34C H 1.4724 0.2377 0.2292 0.134 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 0.0497(6) 0.0617(6) 0.0756(8) 0.0241(5) 0.0005(5) 0.0005(4) O2 0.0339(5) 0.0540(5) 0.0593(6) 0.0073(4) 0.0004(4) 0.0026(4) O3 0.0717(8) 0.0774(8) 0.0938(10) -0.0454(7) 0.0071(7) 0.0009(6) O4 0.0507(6) 0.0942(9) 0.0588(6) -0.0215(6) 0.0044(5) 0.0243(6) O5 0.0712(8) 0.1410(13) 0.0354(6) -0.0155(6) 0.0067(5) 0.0130(8) O6 0.0568(6) 0.0679(6) 0.0470(6) -0.0025(4) -0.0138(5) -0.0114(5) O7 0.0541(6) 0.0786(7) 0.0561(6) 0.0267(5) 0.0059(5) 0.0073(5) O8 0.0353(5) 0.0847(7) 0.0535(6) 0.0190(5) 0.0054(4) 0.0106(4) C1 0.0331(6) 0.0446(6) 0.0316(6) -0.0007(4) 0.0033(4) -0.0015(4) C2 0.0331(6) 0.0459(6) 0.0325(6) 0.0007(4) 0.0031(4) 0.0000(4) C3 0.0371(6) 0.0478(6) 0.0339(6) -0.0036(5) 0.0048(5) 0.0038(5) C4 0.0371(6) 0.0499(6) 0.0310(6) -0.0026(5) 0.0015(5) 0.0013(5) C5 0.0336(6) 0.0462(6) 0.0313(6) 0.0007(4) 0.0034(4) 0.0012(4) C6 0.0340(6) 0.0435(6) 0.0325(6) 0.0000(4) 0.0047(4) -0.0003(4) C7 0.0339(6) 0.0434(6) 0.0344(6) -0.0032(4) 0.0009(4) 0.0015(4) C8 0.0429(7) 0.0657(8) 0.0383(7) -0.0018(5) 0.0042(5) -0.0104(6) C9 0.0431(7) 0.0772(10) 0.0511(8) -0.0085(7) -0.0021(6) -0.0198(7) C10 0.0470(7) 0.0679(8) 0.0377(7) -0.0090(6) -0.0078(5) -0.0031(6) C11 0.0441(7) 0.0449(6) 0.0350(6) -0.0018(5) 0.0008(5) 0.0070(5) C12 0.0661(9) 0.0560(7) 0.0346(6) 0.0018(5) 0.0044(6) 0.0116(6) C13 0.0776(11) 0.0581(8) 0.0485(8) 0.0107(6) 0.0228(7) 0.0059(7) C14 0.0608(9) 0.0514(8) 0.0635(9) 0.0049(6) 0.0175(7) -0.0069(6) C15 0.0453(7) 0.0452(6) 0.0453(7) -0.0032(5) 0.0050(5) -0.0042(5) C16 0.0363(6) 0.0371(5) 0.0352(6) -0.0023(4) 0.0015(4) 0.0041(4) C17 0.0362(6) 0.0450(6) 0.0308(5) -0.0013(4) 0.0016(4) 0.0023(4) C18 0.0458(7) 0.0502(7) 0.0432(7) 0.0010(5) 0.0114(5) 0.0016(5) C19 0.0515(8) 0.0645(8) 0.0481(7) -0.0023(6) 0.0156(6) 0.0123(6) C20 0.0585(8) 0.0512(7) 0.0457(7) -0.0059(5) 0.0016(6) 0.0150(6) C21 0.0500(7) 0.0459(7) 0.0359(6) 0.0001(5) -0.0091(5) 0.0022(5) C22 0.0675(10) 0.0465(7) 0.0596(9) 0.0033(6) -0.0162(7) -0.0047(6) C23 0.0661(10) 0.0615(9) 0.0749(11) 0.0179(8) -0.0109(8) -0.0212(8) C24 0.0541(9) 0.0853(12) 0.0670(10) 0.0167(8) 0.0080(7) -0.0174(8) C25 0.0469(7) 0.0633(8) 0.0481(7) 0.0038(6) 0.0094(6) -0.0038(6) C26 0.0390(6) 0.0476(7) 0.0307(5) 0.0008(4) -0.0018(4) -0.0008(5) C27 0.0373(6) 0.0464(6) 0.0336(6) -0.0009(4) 0.0022(4) 0.0022(5) C28 0.0358(7) 0.0765(10) 0.0817(11) 0.0127(8) -0.0041(7) 0.0069(7) C29 0.0503(7) 0.0568(8) 0.0359(6) -0.0059(5) 0.0033(5) 0.0113(6) C30 0.0929(16) 0.132(2) 0.0728(13) -0.0252(12) 0.0004(11) 0.0681(15) C31 0.0501(8) 0.0583(7) 0.0345(7) -0.0083(5) -0.0023(5) 0.0103(6) C32 0.0863(14) 0.0850(12) 0.0629(11) -0.0015(8) -0.0358(10) -0.0173(10) C33 0.0377(6) 0.0459(6) 0.0353(6) 0.0011(5) 0.0014(5) 0.0025(5) C34 0.0395(9) 0.1290(18) 0.0974(15) 0.0362(14) 0.0053(9) 0.0227(10) _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 C27 1.1927(17) . ? O2 C27 1.3145(16) . ? O2 C28 1.4462(17) . ? O3 C29 1.187(2) . ? O4 C29 1.3222(19) . ? O4 C30 1.445(2) . ? O5 C31 1.196(2) . ? O6 C31 1.3207(19) . ? O6 C32 1.4519(18) . ? O7 C33 1.1897(17) . ? O8 C33 1.3189(17) . ? O8 C34 1.4474(19) . ? C1 C2 1.3944(17) . ? C1 C6 1.4105(17) . ? C1 C7 1.5045(15) . ? C2 C3 1.3973(17) . ? C2 C27 1.5121(16) . ? C3 C4 1.3942(17) . ? C3 C29 1.4950(17) . ? C4 C5 1.3889(17) . ? C4 C31 1.5020(16) . ? C5 C6 1.4011(16) . ? C5 C33 1.5102(16) . ? C6 C17 1.4935(16) . ? C7 C8 1.3703(18) . ? C7 C16 1.4269(17) . ? C8 C9 1.4075(19) . ? C9 C10 1.351(2) . ? C10 C11 1.412(2) . ? C11 C12 1.4210(19) . ? C11 C16 1.4247(16) . ? C12 C13 1.360(2) . ? C13 C14 1.404(2) . ? C14 C15 1.362(2) . ? C15 C16 1.4161(18) . ? C17 C18 1.3729(18) . ? C17 C26 1.4286(17) . ? C18 C19 1.407(2) . ? C19 C20 1.358(2) . ? C20 C21 1.412(2) . ? C21 C22 1.416(2) . ? C21 C26 1.4190(18) . ? C22 C23 1.355(3) . ? C23 C24 1.401(3) . ? C24 C25 1.362(2) . ? C25 C26 1.4154(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 C27 O2 C28 116.31(11) . . ? C29 O4 C30 116.40(16) . . ? C31 O6 C32 115.11(15) . . ? C33 O8 C34 116.32(13) . . ? C2 C1 C6 119.19(10) . . ? C2 C1 C7 119.67(10) . . ? C6 C1 C7 121.12(10) . . ? C1 C2 C3 121.27(11) . . ? C1 C2 C27 119.95(10) . . ? C3 C2 C27 118.69(11) . . ? C4 C3 C2 119.45(11) . . ? C4 C3 C29 118.67(11) . . ? C2 C3 C29 121.78(11) . . ? C5 C4 C3 119.76(11) . . ? C5 C4 C31 118.92(11) . . ? C3 C4 C31 121.08(11) . . ? C4 C5 C6 121.24(11) . . ? C4 C5 C33 117.78(10) . . ? C6 C5 C33 120.82(10) . . ? C5 C6 C1 119.01(11) . . ? C5 C6 C17 118.83(10) . . ? C1 C6 C17 121.82(10) . . ? C8 C7 C16 119.69(11) . . ? C8 C7 C1 120.59(11) . . ? C16 C7 C1 119.64(10) . . ? C7 C8 C9 120.95(13) . . ? C10 C9 C8 120.69(13) . . ? C9 C10 C11 120.61(12) . . ? C10 C11 C12 121.58(13) . . ? C10 C11 C16 119.46(12) . . ? C12 C11 C16 118.95(13) . . ? C13 C12 C11 121.15(13) . . ? C12 C13 C14 119.85(14) . . ? C15 C14 C13 120.79(15) . . ? C14 C15 C16 121.23(13) . . ? C15 C16 C11 118.03(11) . . ? C15 C16 C7 123.39(11) . . ? C11 C16 C7 118.59(11) . . ? C18 C17 C26 119.74(11) . . ? C18 C17 C6 121.73(11) . . ? C26 C17 C6 118.36(10) . . ? C17 C18 C19 120.77(13) . . ? C20 C19 C18 120.58(14) . . ? C19 C20 C21 120.68(12) . . ? C20 C21 C22 121.52(14) . . ? C20 C21 C26 119.38(12) . . ? C22 C21 C26 119.10(14) . . ? C23 C22 C21 121.02(16) . . ? C22 C23 C24 120.11(14) . . ? C25 C24 C23 120.60(16) . . ? C24 C25 C26 121.06(15) . . ? C25 C26 C21 118.09(12) . . ? C25 C26 C17 123.07(12) . . ? C21 C26 C17 118.83(12) . . ? O1 C27 O2 125.58(12) . . ? O1 C27 C2 122.60(12) . . ? O2 C27 C2 111.81(10) . . ? O3 C29 O4 124.76(13) . . ? O3 C29 C3 123.65(14) . . ? O4 C29 C3 111.59(12) . . ? O5 C31 O6 125.79(13) . . ? O5 C31 C4 123.23(14) . . ? O6 C31 C4 110.81(12) . . ? O7 C33 O8 125.24(12) . . ? O7 C33 C5 123.07(12) . . ? O8 C33 C5 111.64(10) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 67.99 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.347 _refine_diff_density_min -0.300 _refine_diff_density_rms 0.035 # Attachment '- ic13752N6p.cif' data_ic13752 _database_code_depnum_ccdc_archive 'CCDC 728463' #TrackingRef '- ic13752N6p.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C69 H61 Cl4 O24.50' _chemical_formula_weight 1423.98 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 '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 12.0972(3) _cell_length_b 14.9120(4) _cell_length_c 20.7722(6) _cell_angle_alpha 72.261(2) _cell_angle_beta 77.370(2) _cell_angle_gamma 89.011(2) _cell_volume 3477.73(16) _cell_formula_units_Z 2 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 13400 _cell_measurement_theta_min 3.1132 _cell_measurement_theta_max 77.5561 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.360 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1478 _exptl_absorpt_coefficient_mu 2.223 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.75462 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET) (compiled Feb 27 2009,15:38:38) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Gemini A' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 28484 _diffrn_reflns_av_R_equivalents 0.0331 _diffrn_reflns_av_sigmaI/netI 0.0371 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.12 _diffrn_reflns_theta_max 68.00 _reflns_number_total 12637 _reflns_number_gt 9487 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET) (compiled Feb 27 2009,15:38:38) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET) (compiled Feb 27 2009,15:38:38) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET) (compiled Feb 27 2009,15:38:38) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _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^)+(0.1000P)^2^+0.0000P] 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 12637 _refine_ls_number_parameters 904 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0939 _refine_ls_R_factor_gt 0.0739 _refine_ls_wR_factor_ref 0.2212 _refine_ls_wR_factor_gt 0.2115 _refine_ls_goodness_of_fit_ref 1.555 _refine_ls_restrained_S_all 1.555 _refine_ls_shift/su_max 0.003 _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 0.09899(19) 0.86978(16) 0.70094(12) 0.0414(5) Uani 1 1 d . . . O2 O 0.0226(2) 0.72233(19) 0.74526(15) 0.0532(6) Uani 1 1 d . . . O3 O 0.0737(2) 0.6205(2) 0.59919(16) 0.0573(7) Uani 1 1 d . . . O4 O 0.0276(2) 0.7681(2) 0.59441(18) 0.0659(8) Uani 1 1 d . . . O5 O 0.2526(2) 0.71005(19) 0.47828(12) 0.0494(6) Uani 1 1 d . . . O6 O 0.3452(2) 0.58101(18) 0.51826(13) 0.0486(6) Uani 1 1 d . . . O7 O 0.57012(19) 0.61063(16) 0.59199(12) 0.0419(5) Uani 1 1 d . . . O8 O 0.5459(2) 0.72393(19) 0.49708(12) 0.0519(6) Uani 1 1 d . . . O9 O 0.3297(2) 1.10381(18) 0.64669(12) 0.0466(5) Uani 1 1 d . . . O10 O 0.19389(18) 1.05383(17) 0.74399(13) 0.0440(5) Uani 1 1 d . . . O11 O 0.46617(19) 1.32044(15) 0.65639(12) 0.0412(5) Uani 1 1 d . . . O12 O 0.2859(2) 1.27079(18) 0.70592(16) 0.0590(7) Uani 1 1 d . . . O13 O 0.6670(2) 1.29357(17) 0.75036(13) 0.0459(5) Uani 1 1 d . . . O14 O 0.4918(2) 1.32895(18) 0.79411(16) 0.0560(7) Uani 1 1 d . . . O15 O 0.6358(2) 1.15739(19) 0.88851(12) 0.0474(6) Uani 1 1 d . . . O16 O 0.7441(2) 1.0666(2) 0.83433(17) 0.0599(7) Uani 1 1 d . . . O17 O 0.00643(19) 0.88052(15) 0.90969(11) 0.0374(5) Uani 1 1 d . . . O18 O 0.1000(2) 0.93031(15) 0.97572(12) 0.0407(5) Uani 1 1 d . . . O19 O -0.1283(2) 0.80382(18) 1.06463(12) 0.0442(5) Uani 1 1 d . . . O20 O -0.0364(2) 0.7733(2) 1.15107(13) 0.0548(7) Uani 1 1 d . . . O21 O -0.10746(19) 0.57238(18) 1.17122(11) 0.0446(5) Uani 1 1 d . . . O22 O 0.0569(2) 0.5407(2) 1.20303(13) 0.0618(7) Uani 1 1 d . . . O23 O 0.07184(18) 0.42537(14) 1.07911(11) 0.0359(4) Uani 1 1 d . . . O24 O 0.24095(19) 0.45080(16) 1.09939(13) 0.0447(5) Uani 1 1 d . . . C1 C 0.3089(2) 0.79129(19) 0.75566(13) 0.0269(5) Uani 1 1 d . . . C2 C 0.3686(2) 0.87522(19) 0.74614(13) 0.0278(5) Uani 1 1 d . . . H2A H 0.4127 0.9088 0.7016 0.033 Uiso 1 1 calc R . . C3 C 0.3639(2) 0.91001(18) 0.80165(13) 0.0265(5) Uani 1 1 d . . . C4 C 0.3007(2) 0.85911(18) 0.86709(13) 0.0266(5) Uani 1 1 d . . . H4A H 0.2986 0.8821 0.9052 0.032 Uiso 1 1 calc R . . C5 C 0.2410(2) 0.77550(18) 0.87746(13) 0.0253(5) Uani 1 1 d . . . C6 C 0.2451(2) 0.74201(18) 0.82122(14) 0.0271(5) Uani 1 1 d . . . H6A H 0.2040 0.6851 0.8277 0.033 Uiso 1 1 calc R . . C7 C 0.3102(2) 0.75671(18) 0.69501(13) 0.0279(5) Uani 1 1 d . . . C8 C 0.2089(2) 0.75025(19) 0.67425(14) 0.0305(6) Uani 1 1 d . . . C9 C 0.2052(2) 0.7151(2) 0.61949(14) 0.0318(6) Uani 1 1 d . . . C10 C 0.3045(3) 0.68971(19) 0.58306(14) 0.0311(6) Uani 1 1 d . . . C11 C 0.4068(2) 0.69805(18) 0.60214(14) 0.0295(5) Uani 1 1 d . . . C12 C 0.4110(2) 0.73007(18) 0.65826(13) 0.0284(5) Uani 1 1 d . . . C13 C 0.5227(2) 0.7338(2) 0.67741(15) 0.0329(6) Uani 1 1 d . . . C14 C 0.6094(3) 0.7980(3) 0.63274(19) 0.0464(7) Uani 1 1 d . . . H14A H 0.5952 0.8446 0.5930 0.056 Uiso 1 1 calc R . . C15 C 0.7169(3) 0.7932(3) 0.6470(3) 0.0645(11) Uani 1 1 d . . . H15A H 0.7762 0.8370 0.6168 0.077 Uiso 1 1 calc R . . C16 C 0.7387(3) 0.7246(4) 0.7052(2) 0.0630(11) Uani 1 1 d . . . H16A H 0.8125 0.7211 0.7144 0.076 Uiso 1 1 calc R . . C17 C 0.6519(3) 0.6622(3) 0.7491(2) 0.0553(9) Uani 1 1 d . . . H17A H 0.6663 0.6153 0.7887 0.066 Uiso 1 1 calc R . . C18 C 0.5441(3) 0.6670(3) 0.73622(17) 0.0444(7) Uani 1 1 d . . . H18A H 0.4845 0.6246 0.7676 0.053 Uiso 1 1 calc R . . C19 C 0.0994(3) 0.7780(2) 0.71167(15) 0.0352(6) Uani 1 1 d . . . C20 C -0.0039(3) 0.9035(3) 0.7335(2) 0.0562(9) Uani 1 1 d . . . H20A H 0.0041 0.9722 0.7225 0.084 Uiso 1 1 calc R . . H20B H -0.0182 0.8743 0.7839 0.084 Uiso 1 1 calc R . . H20C H -0.0676 0.8871 0.7163 0.084 Uiso 1 1 calc R . . C21 C 0.0930(3) 0.7070(3) 0.60186(16) 0.0402(7) Uani 1 1 d . . . C22 C -0.0345(4) 0.6064(5) 0.5833(4) 0.098(2) Uani 1 1 d . . . H22A H -0.0427 0.5416 0.5822 0.147 Uiso 1 1 calc R . . H22B H -0.0377 0.6507 0.5379 0.147 Uiso 1 1 calc R . . H22C H -0.0962 0.6174 0.6189 0.147 Uiso 1 1 calc R . . C23 C 0.3034(3) 0.6524(2) 0.52365(15) 0.0343(6) Uani 1 1 d . . . C24 C 0.2433(4) 0.6805(4) 0.4194(2) 0.0722(14) Uani 1 1 d . . . H24A H 0.2043 0.7278 0.3893 0.108 Uiso 1 1 calc R . . H24B H 0.2000 0.6198 0.4358 0.108 Uiso 1 1 calc R . . H24C H 0.3193 0.6739 0.3934 0.108 Uiso 1 1 calc R . . C25 C 0.5146(2) 0.6794(2) 0.55710(15) 0.0335(6) Uani 1 1 d . . . C26 C 0.6816(3) 0.5975(3) 0.5545(2) 0.0606(10) Uani 1 1 d . . . H26A H 0.7162 0.5458 0.5841 0.091 Uiso 1 1 calc R . . H26B H 0.7292 0.6557 0.5411 0.091 Uiso 1 1 calc R . . H26C H 0.6751 0.5822 0.5128 0.091 Uiso 1 1 calc R . . C27 C 0.4212(2) 1.00277(18) 0.79152(13) 0.0277(5) Uani 1 1 d . . . C28 C 0.3839(2) 1.08507(19) 0.74994(14) 0.0284(5) Uani 1 1 d . . . C29 C 0.4317(2) 1.17328(19) 0.74214(14) 0.0289(5) Uani 1 1 d . . . C30 C 0.5173(2) 1.18001(19) 0.77553(14) 0.0297(5) Uani 1 1 d . . . C31 C 0.5583(2) 1.0978(2) 0.81502(14) 0.0302(5) Uani 1 1 d . . . C32 C 0.5100(2) 1.00899(19) 0.82373(14) 0.0292(5) Uani 1 1 d . . . C33 C 0.5505(2) 0.9223(2) 0.86839(15) 0.0325(6) Uani 1 1 d . . . C34 C 0.5334(3) 0.9066(2) 0.93888(17) 0.0421(7) Uani 1 1 d . . . H34A H 0.4967 0.9519 0.9588 0.051 Uiso 1 1 calc R . . C35 C 0.5696(3) 0.8243(3) 0.98151(18) 0.0541(9) Uani 1 1 d . . . H35A H 0.5578 0.8140 1.0300 0.065 Uiso 1 1 calc R . . C36 C 0.6222(3) 0.7586(3) 0.9525(2) 0.0539(9) Uani 1 1 d . . . H36A H 0.6469 0.7027 0.9811 0.065 Uiso 1 1 calc R . . C37 C 0.6391(3) 0.7740(3) 0.8820(2) 0.0504(8) Uani 1 1 d . . . H37A H 0.6760 0.7287 0.8623 0.060 Uiso 1 1 calc R . . C38 C 0.6029(3) 0.8548(2) 0.83980(17) 0.0408(7) Uani 1 1 d . . . H38A H 0.6138 0.8642 0.7914 0.049 Uiso 1 1 calc R . . C39 C 0.2897(2) 1.07873(19) 0.71459(15) 0.0322(6) Uani 1 1 d . . . C40 C 0.2458(4) 1.1046(4) 0.6060(2) 0.0678(12) Uani 1 1 d . . . H40A H 0.2830 1.1242 0.5566 0.102 Uiso 1 1 calc R . . H40B H 0.1880 1.1490 0.6146 0.102 Uiso 1 1 calc R . . H40C H 0.2100 1.0412 0.6193 0.102 Uiso 1 1 calc R . . C41 C 0.3849(3) 1.2596(2) 0.69995(15) 0.0335(6) Uani 1 1 d . . . C42 C 0.4277(4) 1.4090(2) 0.61635(19) 0.0515(9) Uani 1 1 d . . . H42A H 0.4935 1.4493 0.5858 0.077 Uiso 1 1 calc R . . H42B H 0.3856 1.4412 0.6480 0.077 Uiso 1 1 calc R . . H42C H 0.3782 1.3960 0.5883 0.077 Uiso 1 1 calc R . . C43 C 0.5563(3) 1.2761(2) 0.77460(15) 0.0345(6) Uani 1 1 d . . . C44 C 0.7107(4) 1.3822(3) 0.7525(3) 0.0738(13) Uani 1 1 d . . . H44A H 0.7928 1.3891 0.7335 0.111 Uiso 1 1 calc R . . H44B H 0.6949 1.3831 0.8006 0.111 Uiso 1 1 calc R . . H44C H 0.6740 1.4344 0.7248 0.111 Uiso 1 1 calc R . . C45 C 0.6575(3) 1.1039(2) 0.84647(16) 0.0369(6) Uani 1 1 d . . . C46 C 0.7299(4) 1.1736(4) 0.9171(3) 0.0742(13) Uani 1 1 d . . . H46A H 0.7064 1.2131 0.9472 0.111 Uiso 1 1 calc R . . H46B H 0.7938 1.2055 0.8793 0.111 Uiso 1 1 calc R . . H46C H 0.7530 1.1130 0.9442 0.111 Uiso 1 1 calc R . . C47 C 0.1749(2) 0.72277(18) 0.94863(13) 0.0256(5) Uani 1 1 d . . . C48 C 0.0932(2) 0.76718(18) 0.98598(13) 0.0267(5) Uani 1 1 d . . . C49 C 0.0359(2) 0.7200(2) 1.05401(14) 0.0288(5) Uani 1 1 d . . . C50 C 0.0586(2) 0.6267(2) 1.08574(14) 0.0288(5) Uani 1 1 d . . . C51 C 0.1369(2) 0.58133(19) 1.04815(14) 0.0277(5) Uani 1 1 d . . . C52 C 0.1955(2) 0.62809(18) 0.98036(13) 0.0260(5) Uani 1 1 d . . . C53 C 0.2826(2) 0.57542(18) 0.94551(13) 0.0288(5) Uani 1 1 d . . . C54 C 0.2494(3) 0.5040(2) 0.92211(16) 0.0366(6) Uani 1 1 d . . . H54A H 0.1715 0.4924 0.9244 0.044 Uiso 1 1 calc R . . C55 C 0.3309(3) 0.4498(2) 0.89542(18) 0.0460(8) Uani 1 1 d . . . H55A H 0.3088 0.4014 0.8792 0.055 Uiso 1 1 calc R . . C56 C 0.4442(3) 0.4669(2) 0.89267(17) 0.0483(8) Uani 1 1 d . . . H56A H 0.4998 0.4294 0.8750 0.058 Uiso 1 1 calc R . . C57 C 0.4767(3) 0.5375(3) 0.91535(18) 0.0472(8) Uani 1 1 d . . . H57A H 0.5547 0.5489 0.9131 0.057 Uiso 1 1 calc R . . C58 C 0.3962(3) 0.5924(2) 0.94147(16) 0.0374(6) Uani 1 1 d . . . H58A H 0.4192 0.6417 0.9566 0.045 Uiso 1 1 calc R . . C59 C 0.0684(2) 0.86884(19) 0.95615(13) 0.0289(5) Uani 1 1 d . . . C60 C -0.0319(4) 0.9760(3) 0.88424(19) 0.0511(9) Uani 1 1 d . . . H60A H -0.0769 0.9780 0.8500 0.077 Uiso 1 1 calc R . . H60B H 0.0342 1.0205 0.8626 0.077 Uiso 1 1 calc R . . H60C H -0.0784 0.9933 0.9231 0.077 Uiso 1 1 calc R . . C61 C -0.0459(3) 0.76861(19) 1.09614(14) 0.0330(6) Uani 1 1 d . . . C62 C -0.2148(3) 0.8493(3) 1.1019(2) 0.0573(10) Uani 1 1 d . . . H62A H -0.2714 0.8727 1.0743 0.086 Uiso 1 1 calc R . . H62B H -0.1799 0.9022 1.1104 0.086 Uiso 1 1 calc R . . H62C H -0.2519 0.8037 1.1463 0.086 Uiso 1 1 calc R . . C63 C 0.0034(3) 0.5754(2) 1.16024(15) 0.0343(6) Uani 1 1 d . . . C64 C -0.1690(4) 0.5265(3) 1.2417(2) 0.0642(11) Uani 1 1 d . . . H64A H -0.2507 0.5285 1.2438 0.096 Uiso 1 1 calc R . . H64B H -0.1495 0.5591 1.2724 0.096 Uiso 1 1 calc R . . H64C H -0.1484 0.4607 1.2564 0.096 Uiso 1 1 calc R . . C65 C 0.1586(2) 0.47900(19) 1.07968(14) 0.0296(5) Uani 1 1 d . . . C66 C 0.0876(3) 0.3254(2) 1.0981(2) 0.0452(7) Uani 1 1 d . . . H66A H 0.0198 0.2922 1.0961 0.068 Uiso 1 1 calc R . . H66B H 0.1000 0.3033 1.1454 0.068 Uiso 1 1 calc R . . H66C H 0.1536 0.3127 1.0659 0.068 Uiso 1 1 calc R . . C67 C 0.4046(7) 0.9148(5) 0.4293(4) 0.115(3) Uani 1 1 d . . . H67A H 0.4802 0.9428 0.4173 0.138 Uiso 1 1 d R A . H67B H 0.4102 0.8477 0.4414 0.138 Uiso 1 1 d R . . Cl1 Cl 0.3474(2) 0.95097(14) 0.36023(10) 0.1235(7) Uani 1 1 d . A . Cl2 Cl 0.3283(4) 0.9421(2) 0.5014(2) 0.1227(19) Uani 0.50 1 d P A 1 Cl2' Cl 0.4350(13) 0.9638(5) 0.4784(5) 0.288(7) Uani 0.50 1 d P . 2 C68 C 0.0347(6) 0.2747(7) 0.6970(4) 0.0512(19) Uani 0.50 1 d P B 1 H68A H 0.1022 0.2433 0.7112 0.061 Uiso 0.50 1 calc PR B 1 H68B H 0.0082 0.3153 0.7266 0.061 Uiso 0.50 1 calc PR B 1 Cl3 Cl 0.0753(3) 0.3471(3) 0.60930(13) 0.0836(10) Uani 0.50 1 d P B 1 Cl4 Cl -0.0681(2) 0.1919(2) 0.71138(18) 0.0740(8) Uani 0.50 1 d P B 1 C68' C -0.028(3) 0.2250(12) 0.7081(9) 0.163(12) Uani 0.50 1 d P C 2 H68C H 0.0263 0.1969 0.7372 0.195 Uiso 0.50 1 calc PR C 2 H68D H -0.1013 0.2301 0.7386 0.195 Uiso 0.50 1 calc PR C 2 Cl3' Cl 0.0318(7) 0.3495(5) 0.6427(6) 0.222(5) Uani 0.50 1 d P C 2 Cl4' Cl -0.0430(4) 0.1631(3) 0.6597(3) 0.175(3) Uani 0.50 1 d P C 2 O25 O 0.1236(4) 0.0087(3) 0.5024(3) 0.112(3) Uiso 0.50 1 d PR C 1 H25A H 0.1102 -0.0440 0.4979 0.167 Uiso 0.50 1 calc PR C 1 C69 C 0.0383(4) 0.0337(3) 0.5333(3) 0.119(5) Uiso 0.50 1 d PR C 1 H69A H 0.0214 -0.0246 0.5733 0.143 Uiso 0.50 1 calc PR C 1 H69B H -0.0119 0.0257 0.5034 0.143 Uiso 0.50 1 calc PR C 1 C70 C -0.0342(4) 0.0948(3) 0.5661(3) 0.073(2) Uiso 0.50 1 d PR C 1 H70A H -0.1109 0.0651 0.5853 0.109 Uiso 0.50 1 calc PR C 1 H70B H -0.0373 0.1559 0.5314 0.109 Uiso 0.50 1 calc PR C 1 H70C H -0.0029 0.1041 0.6034 0.109 Uiso 0.50 1 calc PR C 1 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 0.0370(11) 0.0440(12) 0.0433(12) -0.0162(9) -0.0058(9) 0.0088(9) O2 0.0361(12) 0.0573(14) 0.0626(16) -0.0261(13) 0.0084(11) -0.0070(11) O3 0.0429(14) 0.0662(16) 0.0760(18) -0.0354(14) -0.0205(13) -0.0031(12) O4 0.0507(15) 0.082(2) 0.088(2) -0.0456(17) -0.0360(15) 0.0248(15) O5 0.0598(15) 0.0637(15) 0.0350(12) -0.0232(11) -0.0222(11) 0.0219(12) O6 0.0641(15) 0.0469(13) 0.0464(13) -0.0263(11) -0.0202(11) 0.0149(11) O7 0.0388(12) 0.0468(12) 0.0472(12) -0.0235(10) -0.0119(10) 0.0108(9) O8 0.0510(14) 0.0622(15) 0.0328(12) -0.0118(11) 0.0065(10) 0.0067(11) O9 0.0456(13) 0.0596(14) 0.0314(11) -0.0040(10) -0.0159(9) -0.0069(10) O10 0.0298(11) 0.0502(12) 0.0491(13) -0.0103(10) -0.0096(9) -0.0016(9) O11 0.0403(12) 0.0307(10) 0.0427(12) 0.0000(9) -0.0052(9) 0.0021(9) O12 0.0351(13) 0.0431(13) 0.0802(19) 0.0077(12) -0.0130(12) 0.0082(10) O13 0.0425(13) 0.0435(12) 0.0507(13) -0.0176(10) -0.0026(10) -0.0108(10) O14 0.0558(15) 0.0453(13) 0.0795(19) -0.0384(13) -0.0142(13) 0.0074(11) O15 0.0419(13) 0.0672(15) 0.0429(12) -0.0256(11) -0.0168(10) -0.0035(11) O16 0.0387(13) 0.0677(17) 0.085(2) -0.0321(15) -0.0269(13) 0.0145(12) O17 0.0461(12) 0.0357(10) 0.0337(10) -0.0131(8) -0.0135(9) 0.0143(9) O18 0.0521(13) 0.0324(10) 0.0427(12) -0.0162(9) -0.0154(10) 0.0081(9) O19 0.0366(11) 0.0539(13) 0.0432(12) -0.0209(10) -0.0038(9) 0.0143(10) O20 0.0699(17) 0.0638(15) 0.0364(13) -0.0269(11) -0.0086(11) 0.0186(13) O21 0.0363(12) 0.0584(13) 0.0298(11) -0.0068(10) 0.0031(9) -0.0063(10) O22 0.0534(15) 0.087(2) 0.0295(12) 0.0051(12) -0.0097(11) 0.0037(14) O23 0.0326(10) 0.0304(10) 0.0437(11) -0.0078(8) -0.0114(9) -0.0004(8) O24 0.0361(12) 0.0384(11) 0.0542(14) 0.0001(10) -0.0190(10) 0.0027(9) C1 0.0255(12) 0.0309(12) 0.0242(12) -0.0088(10) -0.0054(10) 0.0040(10) C2 0.0302(13) 0.0293(12) 0.0211(12) -0.0053(10) -0.0033(10) 0.0013(10) C3 0.0263(12) 0.0264(12) 0.0268(12) -0.0065(10) -0.0087(10) 0.0036(10) C4 0.0291(13) 0.0284(12) 0.0225(12) -0.0088(10) -0.0050(10) 0.0054(10) C5 0.0251(12) 0.0273(12) 0.0233(12) -0.0070(9) -0.0065(9) 0.0058(9) C6 0.0271(13) 0.0262(12) 0.0269(13) -0.0069(10) -0.0054(10) 0.0023(10) C7 0.0319(14) 0.0276(12) 0.0221(12) -0.0063(10) -0.0035(10) -0.0012(10) C8 0.0324(14) 0.0321(13) 0.0256(13) -0.0088(10) -0.0038(10) -0.0020(10) C9 0.0346(15) 0.0346(13) 0.0266(13) -0.0090(11) -0.0078(11) -0.0003(11) C10 0.0374(15) 0.0314(13) 0.0254(13) -0.0088(10) -0.0089(11) 0.0024(11) C11 0.0338(14) 0.0281(12) 0.0248(12) -0.0067(10) -0.0052(10) 0.0023(10) C12 0.0316(14) 0.0273(12) 0.0241(12) -0.0058(10) -0.0044(10) -0.0015(10) C13 0.0300(14) 0.0401(14) 0.0326(14) -0.0192(12) -0.0043(11) 0.0024(11) C14 0.0423(18) 0.0485(18) 0.0467(18) -0.0162(15) -0.0037(14) -0.0058(14) C15 0.0356(19) 0.079(3) 0.081(3) -0.038(2) 0.0022(18) -0.0169(18) C16 0.0344(18) 0.096(3) 0.079(3) -0.051(3) -0.0207(18) 0.0104(19) C17 0.045(2) 0.083(3) 0.048(2) -0.0275(19) -0.0229(16) 0.0179(18) C18 0.0378(17) 0.061(2) 0.0341(15) -0.0123(14) -0.0101(13) 0.0033(14) C19 0.0315(15) 0.0464(16) 0.0317(14) -0.0168(12) -0.0086(11) 0.0017(12) C20 0.046(2) 0.061(2) 0.066(2) -0.0314(19) -0.0058(17) 0.0187(17) C21 0.0361(16) 0.0568(19) 0.0344(15) -0.0221(14) -0.0109(12) 0.0056(14) C22 0.055(3) 0.133(5) 0.147(6) -0.091(5) -0.041(3) 0.000(3) C23 0.0359(15) 0.0405(15) 0.0287(14) -0.0126(12) -0.0091(11) 0.0031(12) C24 0.079(3) 0.115(4) 0.049(2) -0.048(2) -0.039(2) 0.035(3) C25 0.0326(14) 0.0373(14) 0.0339(15) -0.0166(12) -0.0065(12) 0.0033(11) C26 0.0380(19) 0.075(3) 0.083(3) -0.043(2) -0.0158(18) 0.0202(17) C27 0.0282(13) 0.0285(12) 0.0245(12) -0.0082(10) -0.0018(10) 0.0018(10) C28 0.0261(13) 0.0311(13) 0.0270(13) -0.0084(10) -0.0049(10) 0.0019(10) C29 0.0278(13) 0.0271(12) 0.0286(13) -0.0071(10) -0.0023(10) 0.0031(10) C30 0.0289(13) 0.0309(13) 0.0285(13) -0.0105(10) -0.0024(10) 0.0009(10) C31 0.0286(13) 0.0348(14) 0.0285(13) -0.0120(11) -0.0058(10) 0.0017(10) C32 0.0306(13) 0.0328(13) 0.0253(12) -0.0115(10) -0.0055(10) 0.0051(10) C33 0.0311(14) 0.0321(13) 0.0358(15) -0.0094(11) -0.0120(11) 0.0025(11) C34 0.0448(17) 0.0485(17) 0.0343(15) -0.0119(13) -0.0132(13) 0.0099(14) C35 0.054(2) 0.067(2) 0.0343(17) -0.0016(16) -0.0162(15) 0.0110(17) C36 0.051(2) 0.0464(18) 0.058(2) -0.0001(16) -0.0229(17) 0.0129(15) C37 0.052(2) 0.0434(17) 0.060(2) -0.0148(16) -0.0231(17) 0.0177(15) C38 0.0439(17) 0.0414(16) 0.0405(16) -0.0143(13) -0.0147(13) 0.0115(13) C39 0.0325(15) 0.0278(12) 0.0358(15) -0.0059(11) -0.0122(12) 0.0015(11) C40 0.067(3) 0.090(3) 0.046(2) -0.008(2) -0.0299(19) -0.010(2) C41 0.0338(15) 0.0287(13) 0.0355(14) -0.0072(11) -0.0067(11) 0.0026(11) C42 0.064(2) 0.0315(15) 0.0461(18) 0.0022(13) -0.0057(16) 0.0050(14) C43 0.0378(15) 0.0325(14) 0.0350(14) -0.0124(11) -0.0088(12) 0.0014(12) C44 0.069(3) 0.058(2) 0.093(3) -0.029(2) -0.007(2) -0.027(2) C45 0.0338(16) 0.0385(15) 0.0385(15) -0.0096(12) -0.0112(12) 0.0002(12) C46 0.061(3) 0.111(4) 0.070(3) -0.045(3) -0.033(2) -0.005(2) C47 0.0257(12) 0.0287(12) 0.0233(12) -0.0089(10) -0.0061(10) 0.0008(10) C48 0.0275(13) 0.0293(12) 0.0237(12) -0.0083(10) -0.0066(10) 0.0017(10) C49 0.0284(13) 0.0328(13) 0.0253(13) -0.0096(10) -0.0051(10) 0.0015(10) C50 0.0267(13) 0.0336(13) 0.0251(13) -0.0078(10) -0.0048(10) -0.0016(10) C51 0.0256(13) 0.0293(13) 0.0271(13) -0.0055(10) -0.0081(10) -0.0004(10) C52 0.0239(12) 0.0289(12) 0.0260(12) -0.0080(10) -0.0076(10) 0.0012(10) C53 0.0326(14) 0.0277(12) 0.0228(12) -0.0037(10) -0.0058(10) 0.0059(10) C54 0.0419(16) 0.0331(14) 0.0347(14) -0.0104(11) -0.0090(12) 0.0049(12) C55 0.063(2) 0.0363(15) 0.0408(17) -0.0164(13) -0.0111(15) 0.0127(14) C56 0.056(2) 0.0464(17) 0.0390(17) -0.0135(14) -0.0051(14) 0.0258(15) C57 0.0327(16) 0.060(2) 0.0449(18) -0.0134(15) -0.0058(13) 0.0155(14) C58 0.0326(15) 0.0413(15) 0.0379(15) -0.0130(12) -0.0063(12) 0.0043(12) C59 0.0309(13) 0.0307(13) 0.0233(12) -0.0090(10) -0.0019(10) 0.0046(10) C60 0.070(2) 0.0475(18) 0.0433(18) -0.0174(15) -0.0243(16) 0.0317(17) C61 0.0370(15) 0.0310(13) 0.0270(14) -0.0084(11) 0.0008(11) -0.0013(11) C62 0.0423(19) 0.060(2) 0.069(2) -0.0308(19) 0.0036(17) 0.0153(16) C63 0.0391(16) 0.0343(14) 0.0266(14) -0.0075(11) -0.0043(12) 0.0004(11) C64 0.053(2) 0.082(3) 0.0390(19) -0.0078(19) 0.0123(17) -0.018(2) C65 0.0295(14) 0.0305(13) 0.0248(12) -0.0035(10) -0.0050(10) 0.0019(10) C66 0.0431(18) 0.0323(15) 0.056(2) -0.0094(14) -0.0083(15) -0.0004(12) C67 0.126(6) 0.095(4) 0.097(5) -0.020(4) 0.013(4) 0.029(4) Cl1 0.1455(17) 0.1060(12) 0.0871(10) -0.0146(9) 0.0163(11) 0.0293(11) Cl2 0.157(4) 0.0621(15) 0.091(2) -0.0034(14) 0.063(3) 0.0000(18) Cl2' 0.58(2) 0.137(5) 0.267(10) -0.104(6) -0.299(12) 0.173(9) C68 0.031(3) 0.086(6) 0.031(3) -0.007(4) -0.011(3) 0.013(3) Cl3 0.0785(18) 0.103(2) 0.0484(11) 0.0037(12) -0.0113(11) 0.0119(15) Cl4 0.0509(12) 0.0781(19) 0.0880(18) -0.0094(15) -0.0275(11) -0.0036(11) C68' 0.36(4) 0.075(10) 0.071(10) -0.029(8) -0.069(17) -0.027(16) Cl3' 0.186(7) 0.157(6) 0.442(14) -0.174(9) -0.205(9) 0.074(5) Cl4' 0.145(4) 0.112(3) 0.291(9) -0.038(4) -0.132(5) 0.044(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 O1 C19 1.318(4) . ? O1 C20 1.442(4) . ? O2 C19 1.195(4) . ? O3 C21 1.334(5) . ? O3 C22 1.452(5) . ? O4 C21 1.194(5) . ? O5 C23 1.322(4) . ? O5 C24 1.446(4) . ? O6 C23 1.196(4) . ? O7 C25 1.328(4) . ? O7 C26 1.445(4) . ? O8 C25 1.199(4) . ? O9 C39 1.323(4) . ? O9 C40 1.454(4) . ? O10 C39 1.192(4) . ? O11 C41 1.323(4) . ? O11 C42 1.460(4) . ? O12 C41 1.190(4) . ? O13 C43 1.323(4) . ? O13 C44 1.448(5) . ? O14 C43 1.195(4) . ? O15 C45 1.336(4) . ? O15 C46 1.449(4) . ? O16 C45 1.192(4) . ? O17 C59 1.316(4) . ? O17 C60 1.465(4) . ? O18 C59 1.208(4) . ? O19 C61 1.324(4) . ? O19 C62 1.448(4) . ? O20 C61 1.195(4) . ? O21 C63 1.310(4) . ? O21 C64 1.447(4) . ? O22 C63 1.199(4) . ? O23 C65 1.334(4) . ? O23 C66 1.442(4) . ? O24 C65 1.182(4) . ? C1 C6 1.393(4) . ? C1 C2 1.395(4) . ? C1 C7 1.497(4) . ? C2 C3 1.392(4) . ? C2 H2A 0.9500 . ? C3 C4 1.395(4) . ? C3 C27 1.493(4) . ? C4 C5 1.386(4) . ? C4 H4A 0.9500 . ? C5 C6 1.395(4) . ? C5 C47 1.496(4) . ? C6 H6A 0.9500 . ? C7 C8 1.399(4) . ? C7 C12 1.410(4) . ? C8 C9 1.399(4) . ? C8 C19 1.503(4) . ? C9 C10 1.386(4) . ? C9 C21 1.497(4) . ? C10 C11 1.398(4) . ? C10 C23 1.503(4) . ? C11 C12 1.398(4) . ? C11 C25 1.505(4) . ? C12 C13 1.495(4) . ? C13 C18 1.393(5) . ? C13 C14 1.395(5) . ? C14 C15 1.392(6) . ? C14 H14A 0.9500 . ? C15 C16 1.399(7) . ? C15 H15A 0.9500 . ? C16 C17 1.377(7) . ? C16 H16A 0.9500 . ? C17 C18 1.385(5) . ? C17 H17A 0.9500 . ? C18 H18A 0.9500 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 C28 1.401(4) . ? C27 C32 1.402(4) . ? C28 C29 1.395(4) . ? C28 C39 1.502(4) . ? C29 C30 1.387(4) . ? C29 C41 1.500(4) . ? C30 C31 1.402(4) . ? C30 C43 1.509(4) . ? C31 C32 1.401(4) . ? C31 C45 1.502(4) . ? C32 C33 1.489(4) . ? C33 C34 1.379(4) . ? C33 C38 1.395(4) . ? C34 C35 1.405(5) . ? C34 H34A 0.9500 . ? C35 C36 1.378(6) . ? C35 H35A 0.9500 . ? C36 C37 1.380(6) . ? C36 H36A 0.9500 . ? C37 C38 1.385(5) . ? C37 H37A 0.9500 . ? C38 H38A 0.9500 . ? C40 H40A 0.9800 . ? C40 H40B 0.9800 . ? C40 H40C 0.9800 . ? C42 H42A 0.9800 . ? C42 H42B 0.9800 . ? C42 H42C 0.9800 . ? C44 H44A 0.9800 . ? C44 H44B 0.9800 . ? C44 H44C 0.9800 . ? C46 H46A 0.9800 . ? C46 H46B 0.9800 . ? C46 H46C 0.9800 . ? C47 C48 1.404(4) . ? C47 C52 1.408(4) . ? C48 C49 1.398(4) . ? C48 C59 1.505(4) . ? C49 C50 1.398(4) . ? C49 C61 1.501(4) . ? C50 C51 1.393(4) . ? C50 C63 1.507(4) . ? C51 C52 1.398(4) . ? C51 C65 1.509(4) . ? C52 C53 1.495(4) . ? C53 C58 1.381(4) . ? C53 C54 1.395(4) . ? C54 C55 1.392(5) . ? C54 H54A 0.9500 . ? C55 C56 1.385(6) . ? C55 H55A 0.9500 . ? C56 C57 1.373(6) . ? C56 H56A 0.9500 . ? C57 C58 1.387(5) . ? C57 H57A 0.9500 . ? C58 H58A 0.9500 . ? C60 H60A 0.9800 . ? C60 H60B 0.9800 . ? C60 H60C 0.9800 . ? C62 H62A 0.9800 . ? C62 H62B 0.9800 . ? C62 H62C 0.9800 . ? C64 H64A 0.9800 . ? C64 H64B 0.9800 . ? C64 H64C 0.9800 . ? C66 H66A 0.9800 . ? C66 H66B 0.9800 . ? C66 H66C 0.9800 . ? C67 Cl2' 1.528(11) . ? C67 Cl1 1.668(9) . ? C67 Cl2 1.735(7) . ? C67 H67A 0.9600 . ? C67 H67B 0.9599 . ? Cl2' Cl2' 2.39(2) 2_676 ? Cl2' H67A 1.3921 . ? C68 Cl4 1.682(10) . ? C68 Cl3 1.776(8) . ? C68 H68A 0.9900 . ? C68 H68B 0.9900 . ? C68' Cl4' 1.597(15) . ? C68' Cl3' 1.97(2) . ? C68' H68C 0.9900 . ? C68' H68D 0.9900 . ? O25 C69 1.2077 . ? O25 H25A 0.8400 . ? C69 C70 1.4673 . ? C69 H69A 0.9900 . ? C69 H69B 0.9900 . ? C70 H70A 0.9800 . ? C70 H70B 0.9800 . ? C70 H70C 0.9800 . ? 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 C19 O1 C20 115.6(3) . . ? C21 O3 C22 114.1(4) . . ? C23 O5 C24 116.0(3) . . ? C25 O7 C26 115.1(3) . . ? C39 O9 C40 115.3(3) . . ? C41 O11 C42 115.4(3) . . ? C43 O13 C44 115.3(3) . . ? C45 O15 C46 115.1(3) . . ? C59 O17 C60 115.3(2) . . ? C61 O19 C62 116.0(3) . . ? C63 O21 C64 116.5(3) . . ? C65 O23 C66 115.6(2) . . ? C6 C1 C2 119.6(2) . . ? C6 C1 C7 120.5(2) . . ? C2 C1 C7 119.9(2) . . ? C3 C2 C1 120.3(2) . . ? C3 C2 H2A 119.9 . . ? C1 C2 H2A 119.9 . . ? C2 C3 C4 119.3(2) . . ? C2 C3 C27 121.0(2) . . ? C4 C3 C27 119.7(2) . . ? C5 C4 C3 121.1(2) . . ? C5 C4 H4A 119.4 . . ? C3 C4 H4A 119.4 . . ? C4 C5 C6 119.0(2) . . ? C4 C5 C47 119.4(2) . . ? C6 C5 C47 121.6(2) . . ? C1 C6 C5 120.6(2) . . ? C1 C6 H6A 119.7 . . ? C5 C6 H6A 119.7 . . ? C8 C7 C12 119.0(2) . . ? C8 C7 C1 119.3(2) . . ? C12 C7 C1 121.7(2) . . ? C7 C8 C9 121.4(3) . . ? C7 C8 C19 121.0(2) . . ? C9 C8 C19 117.6(3) . . ? C10 C9 C8 119.5(3) . . ? C10 C9 C21 122.1(3) . . ? C8 C9 C21 118.4(3) . . ? C9 C10 C11 119.7(3) . . ? C9 C10 C23 120.8(3) . . ? C11 C10 C23 119.5(3) . . ? C10 C11 C12 121.3(3) . . ? C10 C11 C25 118.2(2) . . ? C12 C11 C25 120.2(3) . . ? C11 C12 C7 119.1(3) . . ? C11 C12 C13 118.5(2) . . ? C7 C12 C13 122.5(2) . . ? C18 C13 C14 119.8(3) . . ? C18 C13 C12 120.0(3) . . ? C14 C13 C12 120.0(3) . . ? C15 C14 C13 119.4(4) . . ? C15 C14 H14A 120.3 . . ? C13 C14 H14A 120.3 . . ? C14 C15 C16 120.7(4) . . ? C14 C15 H15A 119.7 . . ? C16 C15 H15A 119.7 . . ? C17 C16 C15 119.3(4) . . ? C17 C16 H16A 120.4 . . ? C15 C16 H16A 120.4 . . ? C16 C17 C18 120.8(4) . . ? C16 C17 H17A 119.6 . . ? C18 C17 H17A 119.6 . . ? C17 C18 C13 120.2(3) . . ? C17 C18 H18A 119.9 . . ? C13 C18 H18A 119.9 . . ? O2 C19 O1 125.6(3) . . ? O2 C19 C8 122.8(3) . . ? O1 C19 C8 111.5(3) . . ? O1 C20 H20A 109.5 . . ? O1 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? O1 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? O4 C21 O3 124.7(3) . . ? O4 C21 C9 124.6(3) . . ? O3 C21 C9 110.7(3) . . ? O3 C22 H22A 109.5 . . ? O3 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? O3 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? O6 C23 O5 125.4(3) . . ? O6 C23 C10 123.9(3) . . ? O5 C23 C10 110.7(2) . . ? O5 C24 H24A 109.5 . . ? O5 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? O5 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? O8 C25 O7 125.1(3) . . ? O8 C25 C11 122.6(3) . . ? O7 C25 C11 112.3(3) . . ? O7 C26 H26A 109.5 . . ? O7 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? O7 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C28 C27 C32 119.6(3) . . ? C28 C27 C3 119.1(2) . . ? C32 C27 C3 121.3(2) . . ? C29 C28 C27 120.6(3) . . ? C29 C28 C39 119.5(2) . . ? C27 C28 C39 119.8(2) . . ? C30 C29 C28 120.0(3) . . ? C30 C29 C41 121.4(3) . . ? C28 C29 C41 118.6(3) . . ? C29 C30 C31 119.8(3) . . ? C29 C30 C43 119.0(3) . . ? C31 C30 C43 120.9(3) . . ? C32 C31 C30 120.6(3) . . ? C32 C31 C45 119.2(3) . . ? C30 C31 C45 120.2(3) . . ? C31 C32 C27 119.4(3) . . ? C31 C32 C33 120.2(3) . . ? C27 C32 C33 120.4(3) . . ? C34 C33 C38 119.3(3) . . ? C34 C33 C32 120.2(3) . . ? C38 C33 C32 120.4(3) . . ? C33 C34 C35 120.5(3) . . ? C33 C34 H34A 119.7 . . ? C35 C34 H34A 119.7 . . ? C36 C35 C34 119.6(3) . . ? C36 C35 H35A 120.2 . . ? C34 C35 H35A 120.2 . . ? C35 C36 C37 120.0(3) . . ? C35 C36 H36A 120.0 . . ? C37 C36 H36A 120.0 . . ? C36 C37 C38 120.7(3) . . ? C36 C37 H37A 119.6 . . ? C38 C37 H37A 119.6 . . ? C37 C38 C33 119.9(3) . . ? C37 C38 H38A 120.1 . . ? C33 C38 H38A 120.1 . . ? O10 C39 O9 125.7(3) . . ? O10 C39 C28 124.5(3) . . ? O9 C39 C28 109.7(2) . . ? O9 C40 H40A 109.5 . . ? O9 C40 H40B 109.5 . . ? H40A C40 H40B 109.5 . . ? O9 C40 H40C 109.5 . . ? H40A C40 H40C 109.5 . . ? H40B C40 H40C 109.5 . . ? O12 C41 O11 124.9(3) . . ? O12 C41 C29 123.1(3) . . ? O11 C41 C29 112.0(2) . . ? O11 C42 H42A 109.5 . . ? O11 C42 H42B 109.5 . . ? H42A C42 H42B 109.5 . . ? O11 C42 H42C 109.5 . . ? H42A C42 H42C 109.5 . . ? H42B C42 H42C 109.5 . . ? O14 C43 O13 125.2(3) . . ? O14 C43 C30 122.1(3) . . ? O13 C43 C30 112.7(2) . . ? O13 C44 H44A 109.5 . . ? O13 C44 H44B 109.5 . . ? H44A C44 H44B 109.5 . . ? O13 C44 H44C 109.5 . . ? H44A C44 H44C 109.5 . . ? H44B C44 H44C 109.5 . . ? O16 C45 O15 125.1(3) . . ? O16 C45 C31 123.9(3) . . ? O15 C45 C31 111.0(3) . . ? O15 C46 H46A 109.5 . . ? O15 C46 H46B 109.5 . . ? H46A C46 H46B 109.5 . . ? O15 C46 H46C 109.5 . . ? H46A C46 H46C 109.5 . . ? H46B C46 H46C 109.5 . . ? C48 C47 C52 118.5(2) . . ? C48 C47 C5 120.8(2) . . ? C52 C47 C5 120.6(2) . . ? C49 C48 C47 121.1(2) . . ? C49 C48 C59 117.2(2) . . ? C47 C48 C59 121.6(2) . . ? C50 C49 C48 120.0(2) . . ? C50 C49 C61 118.2(2) . . ? C48 C49 C61 121.7(2) . . ? C51 C50 C49 119.1(2) . . ? C51 C50 C63 119.4(2) . . ? C49 C50 C63 121.5(2) . . ? C50 C51 C52 121.4(2) . . ? C50 C51 C65 120.3(2) . . ? C52 C51 C65 118.3(2) . . ? C51 C52 C47 119.8(2) . . ? C51 C52 C53 117.6(2) . . ? C47 C52 C53 122.5(2) . . ? C58 C53 C54 119.8(3) . . ? C58 C53 C52 119.7(3) . . ? C54 C53 C52 120.3(3) . . ? C55 C54 C53 119.8(3) . . ? C55 C54 H54A 120.1 . . ? C53 C54 H54A 120.1 . . ? C56 C55 C54 119.7(3) . . ? C56 C55 H55A 120.1 . . ? C54 C55 H55A 120.1 . . ? C57 C56 C55 120.4(3) . . ? C57 C56 H56A 119.8 . . ? C55 C56 H56A 119.8 . . ? C56 C57 C58 120.3(3) . . ? C56 C57 H57A 119.9 . . ? C58 C57 H57A 119.9 . . ? C53 C58 C57 120.1(3) . . ? C53 C58 H58A 120.0 . . ? C57 C58 H58A 120.0 . . ? O18 C59 O17 125.6(3) . . ? O18 C59 C48 122.0(3) . . ? O17 C59 C48 112.4(2) . . ? O17 C60 H60A 109.5 . . ? O17 C60 H60B 109.5 . . ? H60A C60 H60B 109.5 . . ? O17 C60 H60C 109.5 . . ? H60A C60 H60C 109.5 . . ? H60B C60 H60C 109.5 . . ? O20 C61 O19 125.6(3) . . ? O20 C61 C49 123.2(3) . . ? O19 C61 C49 111.2(2) . . ? O19 C62 H62A 109.5 . . ? O19 C62 H62B 109.5 . . ? H62A C62 H62B 109.5 . . ? O19 C62 H62C 109.5 . . ? H62A C62 H62C 109.5 . . ? H62B C62 H62C 109.5 . . ? O22 C63 O21 125.3(3) . . ? O22 C63 C50 122.7(3) . . ? O21 C63 C50 112.0(3) . . ? O21 C64 H64A 109.5 . . ? O21 C64 H64B 109.5 . . ? H64A C64 H64B 109.5 . . ? O21 C64 H64C 109.5 . . ? H64A C64 H64C 109.5 . . ? H64B C64 H64C 109.5 . . ? O24 C65 O23 125.5(3) . . ? O24 C65 C51 125.5(3) . . ? O23 C65 C51 109.0(2) . . ? O23 C66 H66A 109.5 . . ? O23 C66 H66B 109.5 . . ? H66A C66 H66B 109.5 . . ? O23 C66 H66C 109.5 . . ? H66A C66 H66C 109.5 . . ? H66B C66 H66C 109.5 . . ? Cl2' C67 Cl1 133.4(5) . . ? Cl2' C67 Cl2 45.8(6) . . ? Cl1 C67 Cl2 113.9(5) . . ? Cl2' C67 H67A 63.3 . . ? Cl1 C67 H67A 108.9 . . ? Cl2 C67 H67A 108.8 . . ? Cl2' C67 H67B 117.5 . . ? Cl1 C67 H67B 108.7 . . ? Cl2 C67 H67B 108.6 . . ? H67A C67 H67B 107.7 . . ? C67 Cl2' Cl2' 153.4(13) . 2_676 ? C67 Cl2' H67A 38.0 . . ? Cl2' Cl2' H67A 115.8 2_676 . ? Cl4 C68 Cl3 113.9(5) . . ? Cl4 C68 H68A 108.8 . . ? Cl3 C68 H68A 108.8 . . ? Cl4 C68 H68B 108.8 . . ? Cl3 C68 H68B 108.8 . . ? H68A C68 H68B 107.7 . . ? Cl4' C68' Cl3' 104.5(9) . . ? Cl4' C68' H68C 110.8 . . ? Cl3' C68' H68C 110.8 . . ? Cl4' C68' H68D 110.8 . . ? Cl3' C68' H68D 110.8 . . ? H68C C68' H68D 108.9 . . ? C69 O25 H25A 109.5 . . ? O25 C69 C70 157.6 . . ? O25 C69 H69A 96.9 . . ? C70 C69 H69A 96.9 . . ? O25 C69 H69B 96.9 . . ? C70 C69 H69B 96.9 . . ? H69A C69 H69B 103.5 . . ? C69 C70 H70A 109.5 . . ? C69 C70 H70B 109.5 . . ? H70A C70 H70B 109.5 . . ? C69 C70 H70C 109.5 . . ? H70A C70 H70C 109.5 . . ? H70B C70 H70C 109.5 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 68.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 2.531 _refine_diff_density_min -0.887 _refine_diff_density_rms 0.091