# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Partha Mukherjee' _publ_contact_author_email psm@ipc.iisc.ernet.in _publ_author_name 'Partha Mukherjee' data_complex-1 _database_code_depnum_ccdc_archive 'CCDC 817019' #TrackingRef '- complex-1-2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H9 O4, C4 H9 N O' _chemical_formula_sum 'C21 H18 N O5' _chemical_formula_weight 364.36 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' N N 0.0061 0.0033 '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' Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' 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 6.6344(12) _cell_length_b 14.612(3) _cell_length_c 19.350(4) _cell_angle_alpha 90.00 _cell_angle_beta 93.758(4) _cell_angle_gamma 90.00 _cell_volume 1871.8(6) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'block shape' _exptl_crystal_colour orange _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.293 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1142 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type EMPIRICAL _exptl_absorpt_correction_T_min 0.658 _exptl_absorpt_correction_T_max 0.709 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scan' _diffrn_detector_area_resol_mean 0.3 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16040 _diffrn_reflns_av_R_equivalents 0.1261 _diffrn_reflns_av_sigmaI/netI 0.1574 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.75 _diffrn_reflns_theta_max 28.12 _reflns_number_total 4430 _reflns_number_gt 1740 _reflns_threshold_expression >2\s(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^ > 2\s(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^)+(0.1035P)^2^+0.4352P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4430 _refine_ls_number_parameters 280 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.2765 _refine_ls_R_factor_gt 0.1349 _refine_ls_wR_factor_ref 0.3020 _refine_ls_wR_factor_gt 0.2389 _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_restrained_S_all 1.075 _refine_ls_shift/su_max 0.039 _refine_ls_shift/su_mean 0.003 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.1411(8) 0.3726(4) 0.8646(3) 0.0405(13) Uani 1 1 d . . . C2 C 0.9312(7) 0.4176(3) 1.0292(2) 0.0344(12) Uani 1 1 d . . . O4 O -0.3458(6) 0.3205(3) 0.7804(2) 0.0640(13) Uani 1 1 d . . . C4 C -0.0356(7) 0.3264(3) 0.8471(3) 0.0374(12) Uani 1 1 d . . . C5 C 0.2491(7) 0.2543(4) 0.9431(3) 0.0435(14) Uani 1 1 d . . . C6 C 1.1260(7) 0.4538(3) 1.0515(3) 0.0373(13) Uani 1 1 d . . . C7 C 0.4685(7) 0.3865(3) 0.9335(3) 0.0398(13) Uani 1 1 d . . . C8 C 0.6209(8) 0.4235(3) 0.9537(3) 0.0420(13) Uani 1 1 d . . . C9 C -0.0696(8) 0.2431(4) 0.8776(3) 0.0432(14) Uani 1 1 d . . . C10 C 0.8095(7) 0.4634(3) 0.9778(2) 0.0345(12) Uani 1 1 d . . . O1 O 0.1755(6) 0.0837(3) 0.9984(3) 0.0845(16) Uani 1 1 d . . . C12 C 0.0733(7) 0.2062(3) 0.9256(3) 0.0447(14) Uani 1 1 d . . . O2 O -0.1295(6) 0.0772(3) 0.9448(3) 0.0966(19) Uani 1 1 d . . . C14 C 1.2472(10) 0.4042(4) 1.1012(3) 0.0547(16) Uani 1 1 d . . . C15 C 0.0386(9) 0.1167(4) 0.9591(3) 0.0610(18) Uani 1 1 d . . . C16 C 0.2862(7) 0.3380(3) 0.9132(3) 0.0385(13) Uani 1 1 d . . . C17 C -0.1860(9) 0.3697(4) 0.7960(3) 0.0511(15) Uani 1 1 d . . . O3 O -0.1597(6) 0.4450(3) 0.7729(2) 0.0790(15) Uani 1 1 d . . . C19 C 0.8707(9) 0.3353(4) 1.0608(3) 0.0508(16) Uani 1 1 d . . . C20 C 1.1841(11) 0.3262(5) 1.1288(4) 0.070(2) Uani 1 1 d . . . C21 C 0.9910(10) 0.2910(5) 1.1090(3) 0.068(2) Uani 1 1 d . . . H5 H 0.941(8) 0.231(4) 1.131(3) 0.079(19) Uiso 1 1 d . . . H1 H -0.187(6) 0.214(3) 0.8675(19) 0.016(11) Uiso 1 1 d . . . H4 H 0.748(7) 0.314(3) 1.046(3) 0.052(16) Uiso 1 1 d . . . H2 H 0.342(6) 0.227(3) 0.977(2) 0.036(13) Uiso 1 1 d . . . H6 H 1.259(8) 0.297(4) 1.163(3) 0.064(18) Uiso 1 1 d . . . H8 H -0.411(11) 0.357(5) 0.747(4) 0.12(3) Uiso 1 1 d . . . O10 O 0.8758(8) 0.0985(4) 0.1965(3) 0.1030(19) Uani 1 1 d . . . C51 C 0.8929(12) -0.0638(6) 0.2506(4) 0.111(3) Uani 1 1 d . . . H51A H 0.8728 -0.1264 0.2636 0.167 Uiso 1 1 calc R . . H51B H 0.8872 -0.0253 0.2906 0.167 Uiso 1 1 calc R . . H51C H 1.0226 -0.0576 0.2318 0.167 Uiso 1 1 calc R . . C50 C 0.5437(11) -0.0948(5) 0.1782(5) 0.119(3) Uani 1 1 d . . . H50A H 0.5723 -0.1526 0.2002 0.179 Uiso 1 1 calc R . . H50B H 0.5208 -0.1037 0.1291 0.179 Uiso 1 1 calc R . . H50C H 0.4253 -0.0685 0.1962 0.179 Uiso 1 1 calc R . . C53 C 0.5658(13) 0.0750(7) 0.1209(5) 0.131(4) Uani 1 1 d D . . H53A H 0.5895 0.1376 0.1087 0.197 Uiso 1 1 calc R . . H53B H 0.4366 0.0700 0.1402 0.197 Uiso 1 1 calc R . . H53C H 0.5677 0.0374 0.0803 0.197 Uiso 1 1 calc R . . N1 N 0.7146(14) -0.0333(7) 0.1918(6) 0.168(5) Uani 1 1 d . . . C52 C 0.7521(19) 0.0393(8) 0.1811(6) 0.145(5) Uani 1 1 d D . . H11 H 0.163(7) 0.424(3) 0.847(2) 0.030(14) Uiso 1 1 d . . . H9 H 1.370(8) 0.431(4) 1.114(3) 0.069(19) Uiso 1 1 d . . . H10 H -0.156(13) 0.004(7) 0.972(5) 0.19(4) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.041(3) 0.032(3) 0.048(4) -0.001(3) 0.003(3) -0.007(3) C2 0.029(3) 0.039(3) 0.035(3) -0.007(2) 0.006(2) -0.012(2) O4 0.059(3) 0.067(3) 0.063(3) 0.003(2) -0.027(2) -0.008(2) C4 0.033(3) 0.038(3) 0.041(3) -0.003(3) 0.001(2) -0.006(2) C5 0.033(3) 0.049(4) 0.047(4) 0.001(3) -0.011(3) -0.001(3) C6 0.036(3) 0.037(3) 0.039(3) -0.005(2) 0.002(2) -0.007(2) C7 0.034(3) 0.038(3) 0.047(3) -0.006(3) 0.003(2) -0.007(2) C8 0.038(3) 0.040(3) 0.048(3) -0.004(3) 0.003(2) -0.005(2) C9 0.031(3) 0.044(3) 0.053(4) -0.005(3) -0.008(3) -0.013(3) C10 0.030(3) 0.039(3) 0.035(3) -0.008(2) 0.002(2) -0.009(2) O1 0.065(3) 0.071(3) 0.111(4) 0.046(3) -0.045(3) -0.025(2) C12 0.035(3) 0.043(3) 0.055(4) 0.003(3) -0.005(3) -0.009(2) O2 0.068(3) 0.075(3) 0.139(5) 0.054(3) -0.051(3) -0.046(3) C14 0.055(4) 0.056(4) 0.051(4) 0.004(3) -0.011(3) -0.010(3) C15 0.054(4) 0.058(4) 0.069(4) 0.013(3) -0.016(3) -0.024(3) C16 0.033(3) 0.035(3) 0.048(3) -0.009(3) 0.001(2) -0.011(2) C17 0.056(4) 0.048(4) 0.048(4) -0.007(3) -0.006(3) 0.000(3) O3 0.070(3) 0.064(3) 0.099(4) 0.028(3) -0.025(3) -0.004(2) C19 0.050(4) 0.051(4) 0.051(4) 0.009(3) -0.004(3) -0.022(3) C20 0.086(5) 0.057(4) 0.064(5) 0.022(4) -0.027(4) -0.010(4) C21 0.082(5) 0.056(4) 0.064(4) 0.022(4) -0.006(4) -0.026(4) O10 0.098(4) 0.093(4) 0.112(4) 0.028(3) -0.041(3) -0.045(3) C51 0.107(7) 0.128(8) 0.094(6) -0.004(5) -0.030(5) 0.038(6) C50 0.080(5) 0.105(6) 0.174(9) -0.075(6) 0.021(5) -0.047(5) C53 0.115(7) 0.157(9) 0.116(8) 0.011(7) -0.043(6) -0.026(6) N1 0.138(8) 0.161(9) 0.214(11) -0.112(9) 0.091(8) -0.087(7) C52 0.185(12) 0.106(8) 0.153(10) -0.046(8) 0.084(9) -0.076(9) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C4 1.375(7) . ? C1 C16 1.396(7) . ? C2 C10 1.409(6) . ? C2 C19 1.418(7) . ? C2 C6 1.436(6) . ? O4 C17 1.301(6) . ? C4 C9 1.377(7) . ? C4 C17 1.499(7) . ? C5 C12 1.385(7) . ? C5 C16 1.381(7) . ? C6 C14 1.412(7) . ? C6 C10 1.415(7) 3_767 ? C7 C8 1.190(6) . ? C7 C16 1.434(6) . ? C8 C10 1.431(6) . ? C9 C12 1.392(7) . ? C10 C6 1.415(7) 3_767 ? O1 C15 1.244(6) . ? C12 C15 1.483(7) . ? O2 C15 1.270(6) . ? C14 C20 1.338(8) . ? C17 O3 1.204(6) . ? C19 C21 1.352(8) . ? C20 C21 1.410(9) . ? O10 C52 1.215(10) . ? C51 N1 1.649(12) . ? C50 N1 1.457(9) . ? C53 C52 1.723(14) . ? N1 C52 1.112(12) . ? 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 C4 C1 C16 121.8(5) . . ? C10 C2 C19 122.8(4) . . ? C10 C2 C6 120.0(4) . . ? C19 C2 C6 117.3(5) . . ? C9 C4 C1 119.3(5) . . ? C9 C4 C17 122.3(5) . . ? C1 C4 C17 118.3(5) . . ? C12 C5 C16 121.2(5) . . ? C14 C6 C10 122.6(5) . 3_767 ? C14 C6 C2 118.4(5) . . ? C10 C6 C2 119.0(5) 3_767 . ? C8 C7 C16 176.1(6) . . ? C7 C8 C10 176.9(6) . . ? C4 C9 C12 120.3(5) . . ? C6 C10 C2 121.0(4) 3_767 . ? C6 C10 C8 119.9(5) 3_767 . ? C2 C10 C8 119.0(4) . . ? C5 C12 C9 119.5(5) . . ? C5 C12 C15 119.5(5) . . ? C9 C12 C15 121.0(5) . . ? C20 C14 C6 122.0(6) . . ? O1 C15 O2 123.5(6) . . ? O1 C15 C12 118.8(5) . . ? O2 C15 C12 117.7(6) . . ? C5 C16 C1 118.0(5) . . ? C5 C16 C7 119.5(5) . . ? C1 C16 C7 122.5(5) . . ? O3 C17 O4 123.7(6) . . ? O3 C17 C4 121.6(5) . . ? O4 C17 C4 114.7(6) . . ? C21 C19 C2 122.1(5) . . ? C14 C20 C21 120.3(7) . . ? C19 C21 C20 119.9(6) . . ? C52 N1 C50 137.4(15) . . ? C52 N1 C51 103.1(11) . . ? C50 N1 C51 118.2(10) . . ? N1 C52 O10 142.0(16) . . ? N1 C52 C53 104.8(12) . . ? O10 C52 C53 113.2(9) . . ? _diffrn_measured_fraction_theta_max 0.969 _diffrn_reflns_theta_full 28.12 _diffrn_measured_fraction_theta_full 0.969 _refine_diff_density_max 0.361 _refine_diff_density_min -0.222 _refine_diff_density_rms 0.055 #==== END data_complex-2 _database_code_depnum_ccdc_archive 'CCDC 817020' #TrackingRef '- complex-1-2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C42 H34 O8, 2(C H Cl3)' _chemical_formula_sum 'C44 H36 Cl6 O8' _chemical_formula_weight 905.47 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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 triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.0622(6) _cell_length_b 10.4386(6) _cell_length_c 13.4203(13) _cell_angle_alpha 96.907(7) _cell_angle_beta 106.550(7) _cell_angle_gamma 114.877(4) _cell_volume 1061.10(14) _cell_formula_units_Z 1 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'block shape' _exptl_crystal_colour orange _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.417 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 459 _exptl_absorpt_coefficient_mu 0.458 _exptl_absorpt_correction_type EMPIRICAL _exptl_absorpt_correction_T_min 0.864 _exptl_absorpt_correction_T_max 0.904 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scan' _diffrn_detector_area_resol_mean 0.3 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19456 _diffrn_reflns_av_R_equivalents 0.1059 _diffrn_reflns_av_sigmaI/netI 0.2502 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.65 _diffrn_reflns_theta_max 30.00 _reflns_number_total 6239 _reflns_number_gt 1515 _reflns_threshold_expression >2\s(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^ > 2\s(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^)+(0.0393P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6239 _refine_ls_number_parameters 322 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2434 _refine_ls_R_factor_gt 0.0466 _refine_ls_wR_factor_ref 0.1247 _refine_ls_wR_factor_gt 0.0921 _refine_ls_goodness_of_fit_ref 0.686 _refine_ls_restrained_S_all 0.686 _refine_ls_shift/su_max 0.176 _refine_ls_shift/su_mean 0.007 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 Cl1 Cl 0.20310(13) 0.11033(12) 0.31756(9) 0.0953(4) Uani 1 1 d . . . Cl2 Cl 0.39612(13) 0.10527(12) 0.52519(8) 0.0970(4) Uani 1 1 d . . . C3 C 0.3730(3) -0.0097(3) 0.9041(3) 0.0401(8) Uani 1 1 d . . . C4 C 0.4832(3) -0.0745(3) 0.8982(3) 0.0411(8) Uani 1 1 d . . . O4 O -0.3848(2) 0.3505(2) 0.88021(16) 0.0567(6) Uani 1 1 d . . . C6 C 0.3912(3) 0.0630(3) 1.0055(3) 0.0394(8) Uani 1 1 d . . . C7 C 0.0767(3) 0.2404(3) 1.0287(3) 0.0413(8) Uani 1 1 d . . . C8 C 0.0196(4) 0.4441(3) 1.2556(3) 0.0538(9) Uani 1 1 d . . . C9 C -0.0544(4) 0.2344(4) 0.9408(3) 0.0490(9) Uani 1 1 d . . . C10 C -0.1603(3) 0.2949(3) 0.9537(3) 0.0425(8) Uani 1 1 d . . . O6 O 0.1501(3) 0.4437(2) 1.33322(19) 0.0708(7) Uani 1 1 d . . . C12 C -0.2970(4) 0.2845(3) 0.8547(3) 0.0498(9) Uani 1 1 d . . . C13 C -0.1362(4) 0.3613(3) 1.0561(3) 0.0454(9) Uani 1 1 d . . . C14 C -0.0043(4) 0.3704(3) 1.1458(3) 0.0445(8) Uani 1 1 d . . . O5 O -0.0682(3) 0.4963(3) 1.27368(18) 0.0811(8) Uani 1 1 d . . . C16 C 0.1848(4) 0.1761(3) 1.0164(2) 0.0460(8) Uani 1 1 d . . . C17 C 0.0999(4) 0.3086(3) 1.1311(3) 0.0439(8) Uani 1 1 d . . . C18 C 0.2783(4) 0.1255(3) 1.0110(2) 0.0452(8) Uani 1 1 d . . . O3 O -0.3218(3) 0.2288(3) 0.7647(2) 0.0736(8) Uani 1 1 d . . . C20 C 0.2325(4) -0.0925(4) 0.7096(3) 0.0626(11) Uani 1 1 d . . . C21 C 0.2478(4) -0.0239(4) 0.8060(3) 0.0525(9) Uani 1 1 d . . . C22 C 0.4602(4) -0.1479(4) 0.7949(3) 0.0554(10) Uani 1 1 d . . . C24 C 0.3403(5) -0.1565(4) 0.7038(3) 0.0668(11) Uani 1 1 d . . . C25 C -0.5196(5) 0.3515(5) 0.7893(3) 0.0615(11) Uani 1 1 d . . . C26 C 0.1753(10) 0.5081(9) 1.4429(4) 0.124(3) Uani 1 1 d . . . Cl3 Cl 0.07239(19) -0.14421(14) 0.38885(11) 0.1539(6) Uani 1 1 d . . . C1S C 0.2597(5) 0.0031(4) 0.3929(3) 0.0713(11) Uani 1 1 d . . . C50 C -0.5995(7) 0.4286(6) 0.8373(4) 0.0804(14) Uani 1 1 d . . . C51 C 0.2711(8) 0.4685(6) 1.5184(4) 0.155(2) Uani 1 1 d . . . H51A H 0.2874 0.5167 1.5893 0.232 Uiso 1 1 calc R . . H51B H 0.3832 0.4970 1.5128 0.232 Uiso 1 1 calc R . . H51C H 0.2102 0.3640 1.5065 0.232 Uiso 1 1 calc R . . H2 H -0.204(3) 0.399(3) 1.0691(19) 0.040(8) Uiso 1 1 d . . . H5 H 0.530(3) -0.186(3) 0.7911(19) 0.039(8) Uiso 1 1 d . . . H3 H -0.074(3) 0.194(3) 0.874(2) 0.029(9) Uiso 1 1 d . . . H4 H 0.181(3) 0.020(3) 0.809(2) 0.049(8) Uiso 1 1 d . . . H1 H 0.190(3) 0.316(2) 1.1952(19) 0.038(7) Uiso 1 1 d . . . H16 H -0.457(3) 0.408(3) 0.748(2) 0.057(10) Uiso 1 1 d . . . H15 H -0.509(4) 0.537(4) 0.877(3) 0.100(15) Uiso 1 1 d . . . H13 H -0.663(5) 0.363(4) 0.874(3) 0.14(2) Uiso 1 1 d . . . H10 H 0.322(4) -0.037(4) 0.357(3) 0.109(13) Uiso 1 1 d . . . H12 H 0.330(3) -0.208(3) 0.635(2) 0.062(10) Uiso 1 1 d . . . H14 H -0.685(4) 0.434(4) 0.783(3) 0.097(12) Uiso 1 1 d . . . H11 H 0.148(4) -0.103(3) 0.649(2) 0.059(10) Uiso 1 1 d . . . H17 H -0.601(4) 0.246(4) 0.749(3) 0.096(14) Uiso 1 1 d . . . H21 H 0.298(7) 0.586(6) 1.458(5) 0.20(4) Uiso 1 1 d . . . H26 H 0.155(6) 0.587(5) 1.449(4) 0.16(2) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0926(7) 0.1290(10) 0.0997(9) 0.0597(8) 0.0378(6) 0.0753(7) Cl2 0.1049(8) 0.1134(9) 0.0643(7) 0.0057(6) 0.0068(6) 0.0657(7) C3 0.0402(18) 0.040(2) 0.046(2) 0.0124(17) 0.0193(16) 0.0223(16) C4 0.0395(18) 0.041(2) 0.050(2) 0.0123(18) 0.0216(17) 0.0226(17) O4 0.0533(13) 0.0676(16) 0.0608(16) 0.0162(13) 0.0127(11) 0.0450(13) C6 0.0358(17) 0.0388(19) 0.054(2) 0.0139(17) 0.0212(16) 0.0233(16) C7 0.0446(19) 0.042(2) 0.049(2) 0.0143(18) 0.0220(17) 0.0277(17) C8 0.054(2) 0.056(2) 0.065(3) 0.017(2) 0.025(2) 0.036(2) C9 0.055(2) 0.051(2) 0.052(3) 0.011(2) 0.025(2) 0.033(2) C10 0.0407(18) 0.041(2) 0.054(2) 0.0147(18) 0.0186(17) 0.0252(17) O6 0.0859(17) 0.0949(19) 0.0495(16) 0.0063(14) 0.0157(13) 0.0685(16) C12 0.045(2) 0.044(2) 0.063(3) 0.013(2) 0.016(2) 0.0261(18) C13 0.045(2) 0.045(2) 0.065(3) 0.022(2) 0.0255(19) 0.0323(18) C14 0.0495(19) 0.046(2) 0.051(2) 0.0150(18) 0.0233(17) 0.0311(18) O5 0.0859(17) 0.112(2) 0.0786(19) 0.0107(15) 0.0331(14) 0.0781(17) C16 0.0455(18) 0.053(2) 0.055(2) 0.0169(17) 0.0238(16) 0.0335(18) C17 0.0428(19) 0.053(2) 0.050(2) 0.0186(19) 0.0176(17) 0.0332(18) C18 0.0477(19) 0.046(2) 0.055(2) 0.0139(17) 0.0244(16) 0.0302(18) O3 0.0803(17) 0.093(2) 0.0583(18) 0.0066(16) 0.0157(15) 0.0609(16) C20 0.057(2) 0.082(3) 0.052(3) 0.018(2) 0.012(2) 0.041(2) C21 0.049(2) 0.066(3) 0.054(3) 0.017(2) 0.0177(19) 0.038(2) C22 0.062(2) 0.060(3) 0.060(3) 0.012(2) 0.030(2) 0.040(2) C24 0.082(3) 0.080(3) 0.045(3) 0.005(2) 0.024(2) 0.047(2) C25 0.055(2) 0.068(3) 0.065(3) 0.020(3) 0.009(2) 0.040(3) C26 0.177(7) 0.177(6) 0.045(3) -0.008(4) 0.010(3) 0.137(7) Cl3 0.1550(12) 0.0977(10) 0.1227(12) 0.0314(9) 0.0206(9) 0.0048(9) C1S 0.085(3) 0.076(3) 0.057(3) 0.007(2) 0.010(2) 0.055(3) C50 0.072(3) 0.093(4) 0.092(4) 0.024(3) 0.016(3) 0.063(3) C51 0.273(7) 0.186(6) 0.058(3) 0.032(4) 0.048(4) 0.164(6) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 Cl1 C1S 1.732(3) . ? Cl2 C1S 1.733(4) . ? C3 C6 1.405(4) . ? C3 C21 1.415(4) . ? C3 C4 1.435(3) . ? C4 C6 1.410(4) 2_657 ? C4 C22 1.413(4) . ? O4 C12 1.336(3) . ? O4 C25 1.465(3) . ? C6 C4 1.410(4) 2_657 ? C6 C18 1.440(3) . ? C7 C17 1.383(4) . ? C7 C9 1.388(4) . ? C7 C16 1.434(3) . ? C8 O5 1.198(3) . ? C8 O6 1.336(3) . ? C8 C14 1.488(4) . ? C9 C10 1.388(4) . ? C10 C13 1.374(4) . ? C10 C12 1.491(4) . ? O6 C26 1.453(5) . ? C12 O3 1.189(3) . ? C13 C14 1.395(4) . ? C14 C17 1.391(3) . ? C16 C18 1.185(3) . ? C20 C21 1.342(4) . ? C20 C24 1.409(4) . ? C22 C24 1.349(4) . ? C25 C50 1.490(5) . ? C26 C51 1.361(6) . ? Cl3 C1S 1.726(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C3 C21 122.6(3) . . ? C6 C3 C4 119.5(3) . . ? C21 C3 C4 117.9(3) . . ? C6 C4 C22 122.7(3) 2_657 . ? C6 C4 C3 119.3(3) 2_657 . ? C22 C4 C3 117.9(3) . . ? C12 O4 C25 116.1(3) . . ? C3 C6 C4 121.2(2) . 2_657 ? C3 C6 C18 119.3(3) . . ? C4 C6 C18 119.5(3) 2_657 . ? C17 C7 C9 118.2(3) . . ? C17 C7 C16 119.6(3) . . ? C9 C7 C16 122.1(3) . . ? O5 C8 O6 123.2(3) . . ? O5 C8 C14 124.6(3) . . ? O6 C8 C14 112.2(3) . . ? C7 C9 C10 121.7(3) . . ? C13 C10 C9 119.3(3) . . ? C13 C10 C12 122.6(3) . . ? C9 C10 C12 118.1(3) . . ? C8 O6 C26 115.0(3) . . ? O3 C12 O4 124.2(3) . . ? O3 C12 C10 124.8(3) . . ? O4 C12 C10 111.0(3) . . ? C10 C13 C14 120.3(3) . . ? C13 C14 C17 119.5(3) . . ? C13 C14 C8 119.0(3) . . ? C17 C14 C8 121.5(3) . . ? C18 C16 C7 177.1(3) . . ? C7 C17 C14 121.0(3) . . ? C16 C18 C6 179.2(3) . . ? C21 C20 C24 120.0(4) . . ? C20 C21 C3 122.1(3) . . ? C24 C22 C4 121.8(3) . . ? C22 C24 C20 120.3(4) . . ? O4 C25 C50 106.3(3) . . ? C51 C26 O6 112.9(4) . . ? Cl3 C1S Cl2 110.8(2) . . ? Cl3 C1S Cl1 109.65(19) . . ? Cl2 C1S Cl1 111.1(2) . . ? _diffrn_measured_fraction_theta_max 0.928 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.928 _refine_diff_density_max 0.271 _refine_diff_density_min -0.286 _refine_diff_density_rms 0.043