# Electronic Supplementary Material (ESI) for Green Chemistry # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_aac-22 _database_code_depnum_ccdc_archive 'CCDC 878459' #TrackingRef 'aac-22.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C32 H26 N2 O5, 2(C H Cl3)' _chemical_formula_sum 'C34 H28 Cl6 N2 O5' _chemical_formula_weight 757.28 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' 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 11.373(2) _cell_length_b 11.8524(15) _cell_length_c 13.975(2) _cell_angle_alpha 95.484(12) _cell_angle_beta 112.666(17) _cell_angle_gamma 91.976(13) _cell_volume 1725.0(5) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 4317 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 26.0 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.458 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 776 _exptl_absorpt_coefficient_mu 0.542 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8900 _exptl_absorpt_correction_T_max 0.9182 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13009 _diffrn_reflns_av_R_equivalents 0.0236 _diffrn_reflns_av_sigmaI/netI 0.0527 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.96 _diffrn_reflns_theta_max 26.00 _reflns_number_total 6767 _reflns_number_gt 4317 _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^)+(0.1214P)^2^+1.6103P] 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 6767 _refine_ls_number_parameters 424 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1296 _refine_ls_R_factor_gt 0.0871 _refine_ls_wR_factor_ref 0.2639 _refine_ls_wR_factor_gt 0.2353 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _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 C2 C -0.0542(5) 0.6794(5) 0.2421(4) 0.0812(17) Uani 1 1 d . . . H2 H -0.1154 0.6393 0.1761 0.097 Uiso 1 1 calc R . . Cl4 Cl 0.09897(16) 0.66652(16) 0.24587(14) 0.1042(6) Uani 1 1 d . . . Cl5 Cl -0.0857(2) 0.8194(2) 0.24789(19) 0.1387(9) Uani 1 1 d . . . Cl6 Cl -0.0740(3) 0.6203(3) 0.3444(2) 0.1854(14) Uani 1 1 d . . . C3 C 0.7513(5) 1.5635(4) 0.5799(4) 0.0648(14) Uani 1 1 d . . . H3 H 0.8074 1.6226 0.5801 0.078 Uiso 1 1 calc R . . C4 C 0.7006(5) 1.5683(4) 0.6569(4) 0.0651(15) Uani 1 1 d . . . H4 H 0.7239 1.6307 0.7079 0.078 Uiso 1 1 calc R . . C5 C 0.6190(5) 1.4844(4) 0.6585(4) 0.0606(13) Uani 1 1 d . . . H5 H 0.5872 1.4891 0.7108 0.073 Uiso 1 1 calc R . . C6 C 0.5808(4) 1.3888(3) 0.5811(3) 0.0456(10) Uani 1 1 d . . . C7 C 0.6313(4) 1.3836(3) 0.5033(3) 0.0429(10) Uani 1 1 d . . . C8 C 0.7186(4) 1.4722(3) 0.5042(3) 0.0536(12) Uani 1 1 d . . . H8 H 0.7534 1.4685 0.4539 0.064 Uiso 1 1 calc R . . C9 C 0.5127(4) 1.2153(3) 0.4277(3) 0.0335(8) Uani 1 1 d . . . C10 C 0.4621(4) 1.2204(3) 0.5075(3) 0.0401(9) Uani 1 1 d . . . C11 C 0.3707(4) 1.1301(3) 0.5058(3) 0.0403(9) Uani 1 1 d . . . C12 C 0.3138(5) 1.1323(4) 0.5793(3) 0.0553(12) Uani 1 1 d . . . H12 H 0.3333 1.1942 0.6305 0.066 Uiso 1 1 calc R . . C13 C 0.2304(5) 1.0450(5) 0.5766(4) 0.0642(13) Uani 1 1 d . . . H13 H 0.1938 1.0482 0.6258 0.077 Uiso 1 1 calc R . . C14 C 0.1999(5) 0.9521(4) 0.5017(4) 0.0611(13) Uani 1 1 d . . . H14 H 0.1439 0.8928 0.5012 0.073 Uiso 1 1 calc R . . C15 C 0.2522(4) 0.9468(4) 0.4278(3) 0.0505(11) Uani 1 1 d . . . H15 H 0.2312 0.8842 0.3773 0.061 Uiso 1 1 calc R . . C16 C 0.3379(4) 1.0365(3) 0.4285(3) 0.0385(9) Uani 1 1 d . . . C17 C 0.3912(4) 1.0369(3) 0.3498(3) 0.0364(9) Uani 1 1 d . . . C18 C 0.4709(4) 1.1210(3) 0.3453(3) 0.0342(8) Uani 1 1 d . . . C19 C 0.5137(4) 1.1207(3) 0.2554(3) 0.0320(8) Uani 1 1 d . . . H19 H 0.6048 1.1460 0.2829 0.038 Uiso 1 1 calc R . . C20 C 0.4949(4) 1.0009(3) 0.2021(3) 0.0338(8) Uani 1 1 d . . . C21 C 0.4142(4) 0.9219(3) 0.2123(3) 0.0369(9) Uani 1 1 d . . . C22 C 0.3829(4) 0.8039(3) 0.1581(3) 0.0448(10) Uani 1 1 d . . . H22A H 0.2920 0.7840 0.1352 0.054 Uiso 1 1 calc R . . H22B H 0.4283 0.7514 0.2062 0.054 Uiso 1 1 calc R . . C23 C 0.4200(5) 0.7932(3) 0.0641(3) 0.0509(11) Uani 1 1 d . . . H23A H 0.4166 0.7135 0.0391 0.061 Uiso 1 1 calc R . . H23B H 0.3591 0.8295 0.0083 0.061 Uiso 1 1 calc R . . C24 C 0.5519(5) 0.8471(3) 0.0910(4) 0.0525(11) Uani 1 1 d . . . H24A H 0.5681 0.8461 0.0277 0.063 Uiso 1 1 calc R . . H24B H 0.6136 0.8021 0.1375 0.063 Uiso 1 1 calc R . . C25 C 0.5719(4) 0.9686(3) 0.1427(3) 0.0377(9) Uani 1 1 d . . . C26 C 0.4380(4) 1.2038(3) 0.1812(3) 0.0325(8) Uani 1 1 d . . . C27 C 0.4976(4) 1.3063(3) 0.1769(3) 0.0337(8) Uani 1 1 d . . . H27 H 0.5845 1.3227 0.2161 0.040 Uiso 1 1 calc R . . C28 C 0.4275(4) 1.3840(3) 0.1143(3) 0.0348(8) Uani 1 1 d . . . C29 C 0.2980(4) 1.3588(3) 0.0548(3) 0.0363(9) Uani 1 1 d . . . C30 C 0.2390(4) 1.2554(3) 0.0581(3) 0.0414(9) Uani 1 1 d . . . C31 C 0.3090(4) 1.1777(3) 0.1213(3) 0.0385(9) Uani 1 1 d . . . H31 H 0.2696 1.1085 0.1234 0.046 Uiso 1 1 calc R . . C32 C 0.0508(6) 1.1297(5) -0.0146(5) 0.102(2) Uani 1 1 d . . . H32A H -0.0382 1.1296 -0.0584 0.153 Uiso 1 1 calc R . . H32B H 0.0595 1.1092 0.0525 0.153 Uiso 1 1 calc R . . H32C H 0.0901 1.0759 -0.0463 0.153 Uiso 1 1 calc R . . C33 C 0.1785(5) 1.5172(4) 0.0439(4) 0.0716(15) Uani 1 1 d . . . H33A H 0.1311 1.5682 -0.0037 0.107 Uiso 1 1 calc R . . H33B H 0.2479 1.5595 0.1011 0.107 Uiso 1 1 calc R . . H33C H 0.1233 1.4792 0.0701 0.107 Uiso 1 1 calc R . . C34 C 0.6070(4) 1.5186(4) 0.1631(4) 0.0622(13) Uani 1 1 d . . . H34A H 0.6277 1.5941 0.1521 0.093 Uiso 1 1 calc R . . H34B H 0.6547 1.4660 0.1389 0.093 Uiso 1 1 calc R . . H34C H 0.6283 1.5154 0.2363 0.093 Uiso 1 1 calc R . . N1 N 0.5970(3) 1.2951(2) 0.4263(2) 0.0385(8) Uani 1 1 d . . . N2 N 0.4979(3) 1.3056(3) 0.5837(2) 0.0463(9) Uani 1 1 d . . . O1 O 0.1113(3) 1.2397(2) -0.0022(3) 0.0638(10) Uani 1 1 d . . . O2 O 0.2279(3) 1.4353(2) -0.0091(2) 0.0504(8) Uani 1 1 d . . . O3 O 0.4756(3) 1.4895(2) 0.1077(2) 0.0496(8) Uani 1 1 d . . . O4 O 0.6526(3) 1.0355(2) 0.1367(2) 0.0537(8) Uani 1 1 d . . . O5 O 0.3502(3) 0.9413(2) 0.2768(2) 0.0430(7) Uani 1 1 d . . . C1 C 0.8989(6) 0.2076(5) 0.2502(5) 0.0847(18) Uani 1 1 d . . . H1 H 0.8214 0.1577 0.2103 0.102 Uiso 1 1 calc R . . Cl1 Cl 0.9238(3) 0.2967(3) 0.1687(2) 0.1766(13) Uani 1 1 d . . . Cl2 Cl 1.0238(3) 0.12506(19) 0.2995(2) 0.1607(11) Uani 1 1 d . . . Cl3 Cl 0.8768(2) 0.2857(2) 0.3514(2) 0.1384(8) Uani 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 C2 0.066(4) 0.092(4) 0.061(3) -0.010(3) 0.004(3) -0.002(3) Cl4 0.0778(11) 0.1302(14) 0.0979(12) -0.0013(10) 0.0275(9) 0.0448(10) Cl5 0.1401(19) 0.1357(17) 0.1376(19) -0.0152(14) 0.0537(15) 0.0705(14) Cl6 0.139(2) 0.258(3) 0.148(2) 0.068(2) 0.0396(18) -0.051(2) C3 0.058(3) 0.043(2) 0.065(3) -0.007(2) -0.003(3) 0.004(2) C4 0.065(3) 0.054(3) 0.050(3) -0.020(2) -0.002(2) 0.016(2) C5 0.060(3) 0.060(3) 0.045(3) -0.017(2) 0.006(2) 0.017(2) C6 0.050(2) 0.049(2) 0.029(2) -0.0064(17) 0.0072(18) 0.018(2) C7 0.044(2) 0.038(2) 0.034(2) 0.0002(16) 0.0022(17) 0.0101(17) C8 0.056(3) 0.042(2) 0.049(3) -0.0057(19) 0.009(2) -0.001(2) C9 0.043(2) 0.0327(18) 0.0239(17) 0.0049(14) 0.0117(16) 0.0110(16) C10 0.046(2) 0.042(2) 0.0289(19) 0.0044(16) 0.0092(17) 0.0171(17) C11 0.049(2) 0.046(2) 0.0292(19) 0.0107(16) 0.0176(17) 0.0158(18) C12 0.061(3) 0.075(3) 0.037(2) 0.007(2) 0.026(2) 0.018(2) C13 0.065(3) 0.095(4) 0.048(3) 0.017(3) 0.036(2) 0.010(3) C14 0.062(3) 0.074(3) 0.061(3) 0.020(3) 0.036(3) 0.004(2) C15 0.057(3) 0.053(2) 0.048(2) 0.0127(19) 0.026(2) 0.005(2) C16 0.046(2) 0.040(2) 0.034(2) 0.0111(16) 0.0185(17) 0.0140(17) C17 0.047(2) 0.0324(18) 0.0299(19) 0.0037(15) 0.0152(17) 0.0072(16) C18 0.045(2) 0.0291(17) 0.0284(18) 0.0040(14) 0.0134(16) 0.0085(15) C19 0.042(2) 0.0262(17) 0.0290(18) 0.0023(13) 0.0157(16) 0.0015(14) C20 0.047(2) 0.0240(17) 0.0309(19) 0.0030(14) 0.0154(16) 0.0047(15) C21 0.047(2) 0.0331(19) 0.0316(19) 0.0042(15) 0.0159(17) 0.0041(16) C22 0.063(3) 0.0278(18) 0.045(2) 0.0006(16) 0.024(2) -0.0007(17) C23 0.075(3) 0.031(2) 0.043(2) -0.0066(17) 0.023(2) -0.0002(19) C24 0.075(3) 0.039(2) 0.051(3) -0.0027(18) 0.035(2) 0.005(2) C25 0.048(2) 0.0340(19) 0.032(2) 0.0051(15) 0.0164(17) 0.0074(17) C26 0.048(2) 0.0259(17) 0.0280(18) 0.0003(13) 0.0200(16) 0.0019(15) C27 0.041(2) 0.0315(18) 0.0318(19) 0.0007(14) 0.0183(16) 0.0007(15) C28 0.048(2) 0.0275(17) 0.0332(19) 0.0024(14) 0.0218(17) -0.0037(15) C29 0.050(2) 0.0304(18) 0.0281(18) 0.0054(14) 0.0139(17) 0.0032(16) C30 0.044(2) 0.039(2) 0.037(2) 0.0052(16) 0.0128(18) -0.0072(17) C31 0.049(2) 0.0283(18) 0.037(2) 0.0038(15) 0.0164(18) -0.0047(16) C32 0.065(4) 0.079(4) 0.118(5) 0.039(3) -0.014(3) -0.035(3) C33 0.071(3) 0.056(3) 0.084(4) 0.020(3) 0.022(3) 0.024(2) C34 0.055(3) 0.045(2) 0.085(4) 0.015(2) 0.025(3) -0.012(2) N1 0.0463(19) 0.0338(16) 0.0317(16) 0.0016(13) 0.0117(14) 0.0070(14) N2 0.054(2) 0.053(2) 0.0277(17) -0.0029(14) 0.0115(15) 0.0164(17) O1 0.0489(18) 0.0541(18) 0.067(2) 0.0202(15) -0.0025(16) -0.0135(14) O2 0.0616(19) 0.0423(15) 0.0415(16) 0.0149(12) 0.0115(14) 0.0045(13) O3 0.0510(18) 0.0365(14) 0.0590(18) 0.0174(13) 0.0173(14) -0.0075(12) O4 0.064(2) 0.0474(16) 0.0621(19) -0.0027(14) 0.0403(17) -0.0039(14) O5 0.0576(18) 0.0339(14) 0.0429(15) -0.0025(11) 0.0284(14) -0.0085(12) C1 0.068(4) 0.084(4) 0.093(4) 0.013(3) 0.022(3) -0.010(3) Cl1 0.190(3) 0.209(3) 0.133(2) 0.0905(19) 0.0525(19) -0.012(2) Cl2 0.140(2) 0.1157(16) 0.180(2) 0.0294(16) 0.0055(17) 0.0543(14) Cl3 0.141(2) 0.1446(19) 0.153(2) 0.0110(16) 0.0851(17) 0.0057(15) _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 C2 Cl5 1.711(6) . ? C2 Cl6 1.736(7) . ? C2 Cl4 1.735(6) . ? C2 H2 0.9800 . ? C3 C8 1.370(6) . ? C3 C4 1.402(8) . ? C3 H3 0.9300 . ? C4 C5 1.345(7) . ? C4 H4 0.9300 . ? C5 C6 1.419(6) . ? C5 H5 0.9300 . ? C6 N2 1.354(6) . ? C6 C7 1.409(6) . ? C7 N1 1.358(5) . ? C7 C8 1.416(6) . ? C8 H8 0.9300 . ? C9 N1 1.331(5) . ? C9 C10 1.436(5) . ? C9 C18 1.448(5) . ? C10 N2 1.324(5) . ? C10 C11 1.458(6) . ? C11 C16 1.403(5) . ? C11 C12 1.408(6) . ? C12 C13 1.368(7) . ? C12 H12 0.9300 . ? C13 C14 1.379(7) . ? C13 H13 0.9300 . ? C14 C15 1.373(6) . ? C14 H14 0.9300 . ? C15 C16 1.414(6) . ? C15 H15 0.9300 . ? C16 C17 1.446(5) . ? C17 C18 1.346(5) . ? C17 O5 1.385(4) . ? C18 C19 1.512(5) . ? C19 C20 1.507(5) . ? C19 C26 1.533(5) . ? C19 H19 0.9800 . ? C20 C21 1.344(5) . ? C20 C25 1.458(5) . ? C21 O5 1.368(5) . ? C21 C22 1.487(5) . ? C22 C23 1.522(6) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 C24 1.501(6) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C24 C25 1.515(5) . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C25 O4 1.225(5) . ? C26 C31 1.386(5) . ? C26 C27 1.388(5) . ? C27 C28 1.385(5) . ? C27 H27 0.9300 . ? C28 O3 1.373(4) . ? C28 C29 1.389(5) . ? C29 O2 1.382(4) . ? C29 C30 1.390(5) . ? C30 O1 1.364(5) . ? C30 C31 1.388(5) . ? C31 H31 0.9300 . ? C32 O1 1.416(5) . ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 0.9600 . ? C33 O2 1.424(6) . ? C33 H33A 0.9600 . ? C33 H33B 0.9600 . ? C33 H33C 0.9600 . ? C34 O3 1.405(5) . ? C34 H34A 0.9600 . ? C34 H34B 0.9600 . ? C34 H34C 0.9600 . ? C1 Cl2 1.708(7) . ? C1 Cl1 1.717(6) . ? C1 Cl3 1.721(7) . ? C1 H1 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 Cl5 C2 Cl6 109.3(4) . . ? Cl5 C2 Cl4 110.3(3) . . ? Cl6 C2 Cl4 111.4(3) . . ? Cl5 C2 H2 108.6 . . ? Cl6 C2 H2 108.6 . . ? Cl4 C2 H2 108.6 . . ? C8 C3 C4 120.3(5) . . ? C8 C3 H3 119.8 . . ? C4 C3 H3 119.8 . . ? C5 C4 C3 121.2(4) . . ? C5 C4 H4 119.4 . . ? C3 C4 H4 119.4 . . ? C4 C5 C6 120.6(5) . . ? C4 C5 H5 119.7 . . ? C6 C5 H5 119.7 . . ? N2 C6 C7 121.9(3) . . ? N2 C6 C5 119.7(4) . . ? C7 C6 C5 118.5(4) . . ? N1 C7 C6 121.2(4) . . ? N1 C7 C8 118.9(4) . . ? C6 C7 C8 119.8(4) . . ? C3 C8 C7 119.6(5) . . ? C3 C8 H8 120.2 . . ? C7 C8 H8 120.2 . . ? N1 C9 C10 122.1(3) . . ? N1 C9 C18 118.3(3) . . ? C10 C9 C18 119.5(3) . . ? N2 C10 C9 121.1(4) . . ? N2 C10 C11 119.1(4) . . ? C9 C10 C11 119.9(3) . . ? C16 C11 C12 118.2(4) . . ? C16 C11 C10 119.2(3) . . ? C12 C11 C10 122.6(4) . . ? C13 C12 C11 121.0(4) . . ? C13 C12 H12 119.5 . . ? C11 C12 H12 119.5 . . ? C12 C13 C14 120.8(4) . . ? C12 C13 H13 119.6 . . ? C14 C13 H13 119.6 . . ? C15 C14 C13 120.2(5) . . ? C15 C14 H14 119.9 . . ? C13 C14 H14 119.9 . . ? C14 C15 C16 120.1(4) . . ? C14 C15 H15 119.9 . . ? C16 C15 H15 119.9 . . ? C11 C16 C15 119.7(4) . . ? C11 C16 C17 118.2(3) . . ? C15 C16 C17 122.1(4) . . ? C18 C17 O5 122.5(3) . . ? C18 C17 C16 124.6(3) . . ? O5 C17 C16 112.9(3) . . ? C17 C18 C9 118.4(3) . . ? C17 C18 C19 121.7(3) . . ? C9 C18 C19 119.8(3) . . ? C20 C19 C18 108.6(3) . . ? C20 C19 C26 112.4(3) . . ? C18 C19 C26 109.1(3) . . ? C20 C19 H19 108.9 . . ? C18 C19 H19 108.9 . . ? C26 C19 H19 108.9 . . ? C21 C20 C25 119.2(3) . . ? C21 C20 C19 121.8(3) . . ? C25 C20 C19 118.8(3) . . ? C20 C21 O5 123.0(3) . . ? C20 C21 C22 126.0(4) . . ? O5 C21 C22 111.0(3) . . ? C21 C22 C23 110.7(3) . . ? C21 C22 H22A 109.5 . . ? C23 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? C23 C22 H22B 109.5 . . ? H22A C22 H22B 108.1 . . ? C24 C23 C22 111.5(3) . . ? C24 C23 H23A 109.3 . . ? C22 C23 H23A 109.3 . . ? C24 C23 H23B 109.3 . . ? C22 C23 H23B 109.3 . . ? H23A C23 H23B 108.0 . . ? C23 C24 C25 113.5(4) . . ? C23 C24 H24A 108.9 . . ? C25 C24 H24A 108.9 . . ? C23 C24 H24B 108.9 . . ? C25 C24 H24B 108.9 . . ? H24A C24 H24B 107.7 . . ? O4 C25 C20 121.7(3) . . ? O4 C25 C24 120.7(4) . . ? C20 C25 C24 117.6(3) . . ? C31 C26 C27 120.3(3) . . ? C31 C26 C19 119.6(3) . . ? C27 C26 C19 120.0(3) . . ? C28 C27 C26 120.0(3) . . ? C28 C27 H27 120.0 . . ? C26 C27 H27 120.0 . . ? O3 C28 C27 124.7(3) . . ? O3 C28 C29 115.3(3) . . ? C27 C28 C29 120.0(3) . . ? O2 C29 C28 120.3(3) . . ? O2 C29 C30 119.8(3) . . ? C28 C29 C30 119.9(3) . . ? O1 C30 C31 124.6(3) . . ? O1 C30 C29 115.2(3) . . ? C31 C30 C29 120.2(4) . . ? C26 C31 C30 119.6(3) . . ? C26 C31 H31 120.2 . . ? C30 C31 H31 120.2 . . ? O1 C32 H32A 109.5 . . ? O1 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? O1 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? O2 C33 H33A 109.5 . . ? O2 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? O2 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? O3 C34 H34A 109.5 . . ? O3 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? O3 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? C9 N1 C7 116.5(3) . . ? C10 N2 C6 117.1(4) . . ? C30 O1 C32 117.4(4) . . ? C29 O2 C33 112.8(3) . . ? C28 O3 C34 118.0(3) . . ? C21 O5 C17 117.3(3) . . ? Cl2 C1 Cl1 111.7(4) . . ? Cl2 C1 Cl3 109.4(4) . . ? Cl1 C1 Cl3 110.0(4) . . ? Cl2 C1 H1 108.5 . . ? Cl1 C1 H1 108.5 . . ? Cl3 C1 H1 108.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C8 C3 C4 C5 -0.2(7) . . . . ? C3 C4 C5 C6 -0.6(7) . . . . ? C4 C5 C6 N2 -179.6(4) . . . . ? C4 C5 C6 C7 0.5(6) . . . . ? N2 C6 C7 N1 1.1(6) . . . . ? C5 C6 C7 N1 -179.1(3) . . . . ? N2 C6 C7 C8 -179.5(4) . . . . ? C5 C6 C7 C8 0.4(6) . . . . ? C4 C3 C8 C7 1.1(7) . . . . ? N1 C7 C8 C3 178.2(4) . . . . ? C6 C7 C8 C3 -1.2(6) . . . . ? N1 C9 C10 N2 -0.1(5) . . . . ? C18 C9 C10 N2 -179.8(3) . . . . ? N1 C9 C10 C11 -179.5(3) . . . . ? C18 C9 C10 C11 0.9(5) . . . . ? N2 C10 C11 C16 -176.5(3) . . . . ? C9 C10 C11 C16 2.9(5) . . . . ? N2 C10 C11 C12 3.2(5) . . . . ? C9 C10 C11 C12 -177.5(4) . . . . ? C16 C11 C12 C13 1.0(6) . . . . ? C10 C11 C12 C13 -178.7(4) . . . . ? C11 C12 C13 C14 0.1(7) . . . . ? C12 C13 C14 C15 -0.8(7) . . . . ? C13 C14 C15 C16 0.3(7) . . . . ? C12 C11 C16 C15 -1.4(6) . . . . ? C10 C11 C16 C15 178.2(3) . . . . ? C12 C11 C16 C17 176.9(3) . . . . ? C10 C11 C16 C17 -3.5(5) . . . . ? C14 C15 C16 C11 0.9(6) . . . . ? C14 C15 C16 C17 -177.4(4) . . . . ? C11 C16 C17 C18 0.2(6) . . . . ? C15 C16 C17 C18 178.5(4) . . . . ? C11 C16 C17 O5 -178.9(3) . . . . ? C15 C16 C17 O5 -0.6(5) . . . . ? O5 C17 C18 C9 -177.4(3) . . . . ? C16 C17 C18 C9 3.6(6) . . . . ? O5 C17 C18 C19 4.6(6) . . . . ? C16 C17 C18 C19 -174.5(3) . . . . ? N1 C9 C18 C17 176.3(3) . . . . ? C10 C9 C18 C17 -4.0(5) . . . . ? N1 C9 C18 C19 -5.6(5) . . . . ? C10 C9 C18 C19 174.1(3) . . . . ? C17 C18 C19 C20 -20.4(5) . . . . ? C9 C18 C19 C20 161.6(3) . . . . ? C17 C18 C19 C26 102.4(4) . . . . ? C9 C18 C19 C26 -75.7(4) . . . . ? C18 C19 C20 C21 20.5(5) . . . . ? C26 C19 C20 C21 -100.2(4) . . . . ? C18 C19 C20 C25 -156.0(3) . . . . ? C26 C19 C20 C25 83.3(4) . . . . ? C25 C20 C21 O5 171.9(3) . . . . ? C19 C20 C21 O5 -4.6(6) . . . . ? C25 C20 C21 C22 -7.6(6) . . . . ? C19 C20 C21 C22 176.0(3) . . . . ? C20 C21 C22 C23 -17.8(6) . . . . ? O5 C21 C22 C23 162.7(3) . . . . ? C21 C22 C23 C24 46.6(5) . . . . ? C22 C23 C24 C25 -52.3(5) . . . . ? C21 C20 C25 O4 -175.2(4) . . . . ? C19 C20 C25 O4 1.3(5) . . . . ? C21 C20 C25 C24 2.7(5) . . . . ? C19 C20 C25 C24 179.3(3) . . . . ? C23 C24 C25 O4 -154.5(4) . . . . ? C23 C24 C25 C20 27.5(5) . . . . ? C20 C19 C26 C31 50.3(5) . . . . ? C18 C19 C26 C31 -70.1(4) . . . . ? C20 C19 C26 C27 -131.8(4) . . . . ? C18 C19 C26 C27 107.8(4) . . . . ? C31 C26 C27 C28 1.4(5) . . . . ? C19 C26 C27 C28 -176.5(3) . . . . ? C26 C27 C28 O3 177.1(3) . . . . ? C26 C27 C28 C29 -0.8(5) . . . . ? O3 C28 C29 O2 2.9(5) . . . . ? C27 C28 C29 O2 -179.1(3) . . . . ? O3 C28 C29 C30 -178.2(3) . . . . ? C27 C28 C29 C30 -0.2(6) . . . . ? O2 C29 C30 O1 -1.9(6) . . . . ? C28 C29 C30 O1 179.2(4) . . . . ? O2 C29 C30 C31 179.4(4) . . . . ? C28 C29 C30 C31 0.5(6) . . . . ? C27 C26 C31 C30 -1.1(6) . . . . ? C19 C26 C31 C30 176.8(3) . . . . ? O1 C30 C31 C26 -178.4(4) . . . . ? C29 C30 C31 C26 0.1(6) . . . . ? C10 C9 N1 C7 -1.3(5) . . . . ? C18 C9 N1 C7 178.3(3) . . . . ? C6 C7 N1 C9 0.9(5) . . . . ? C8 C7 N1 C9 -178.6(3) . . . . ? C9 C10 N2 C6 2.0(5) . . . . ? C11 C10 N2 C6 -178.6(3) . . . . ? C7 C6 N2 C10 -2.5(5) . . . . ? C5 C6 N2 C10 177.6(3) . . . . ? C31 C30 O1 C32 -11.1(7) . . . . ? C29 C30 O1 C32 170.3(5) . . . . ? C28 C29 O2 C33 -87.0(5) . . . . ? C30 C29 O2 C33 94.1(4) . . . . ? C27 C28 O3 C34 4.2(6) . . . . ? C29 C28 O3 C34 -177.8(4) . . . . ? C20 C21 O5 C17 -14.0(5) . . . . ? C22 C21 O5 C17 165.5(3) . . . . ? C18 C17 O5 C21 13.9(5) . . . . ? C16 C17 O5 C21 -166.9(3) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.997 _refine_diff_density_min -0.601 _refine_diff_density_rms 0.064