# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Parimal Bharadwaj' _publ_contact_author_email PKB@IITK.AC.IN _publ_section_title ; Binding of various anions in laterally non-symmetric aza-oxa cryptands through H-bonds: characterization of water clusters of different nuclearity ; loop_ _publ_author_name 'Parimal Bharadwaj' 'Madhab C Das' 'Sujit K Ghosh' # Attachment 'B924157D_ccdc_754955_754960_cif.txt' data_Complex1 #TrackingRef 'B924157D_ccdc_754955_754960_cif.txt' _database_code_depnum_ccdc_archive 'CCDC 754955' #TrackingRef 'Complex1-6.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C33 H68 Cl3 N5 O13' _chemical_formula_sum 'C33 H68 Cl3 N5 O13' _chemical_formula_weight 849.28 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' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 13.079(5) _cell_length_b 14.156(4) _cell_length_c 14.444(4) _cell_angle_alpha 107.729(5) _cell_angle_beta 98.846(4) _cell_angle_gamma 116.684(6) _cell_volume 2139.2(12) _cell_formula_units_Z 2 _cell_measurement_temperature 100(1) _cell_measurement_reflns_used ? _cell_measurement_theta_min 2.3 _cell_measurement_theta_max 28.4 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.306 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 904 _exptl_absorpt_coefficient_mu 0.277 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9467 _exptl_absorpt_correction_T_max 0.9571 _exptl_absorpt_process_details 'SADABAS 2.10 (Bruker 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(1) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX' _diffrn_measurement_method /w-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13953 _diffrn_reflns_av_R_equivalents 0.0738 _diffrn_reflns_av_sigmaI/netI 0.1009 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 28.40 _reflns_number_total 10738 _reflns_number_gt 5765 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART 5.628 (Bruker, 2003)' _computing_cell_refinement 'SAINT 6.45 ( Bruker, 2003)' _computing_data_reduction 'SAINT 6.45 (Bruker, 2003)' _computing_structure_solution SIR-97 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Diamond 2.1e' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^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 10738 _refine_ls_number_parameters 477 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1004 _refine_ls_R_factor_gt 0.0747 _refine_ls_wR_factor_ref 0.2286 _refine_ls_wR_factor_gt 0.1607 _refine_ls_goodness_of_fit_ref 1.154 _refine_ls_restrained_S_all 1.154 _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 Cl2 Cl 0.6123(3) 0.2197(3) 0.5834(2) 0.0490(9) Uani 1 1 d . . . O1 O 0.8734(4) 0.3019(4) 0.0370(3) 0.0411(11) Uani 1 1 d . . . O2 O 0.7230(5) 0.5407(4) 0.0223(4) 0.0419(12) Uani 1 1 d . . . O3 O 0.4697(5) 0.1654(4) -0.0114(4) 0.0449(12) Uani 1 1 d . . . N1 N 0.6593(5) 0.2912(5) -0.0963(4) 0.0390(13) Uani 1 1 d . . . N2 N 0.7874(5) 0.4906(5) 0.3734(4) 0.0364(13) Uani 1 1 d . . . N3 N 0.9762(4) 0.5269(4) 0.2654(5) 0.0459(15) Uani 1 1 d . . . H3A H 0.8975 0.4760 0.2253 0.047 Uiso 1 1 calc R . . H3B H 0.9950 0.5979 0.2698 0.047 Uiso 1 1 calc R . . N4 N 0.6462(5) 0.5453(5) 0.2334(4) 0.0397(13) Uani 1 1 d . . . H4A H 0.6805 0.5065 0.2050 0.036 Uiso 1 1 calc R . . H4B H 0.5716 0.4921 0.2283 0.036 Uiso 1 1 calc R . . C26 C 0.7506(4) 0.6928(4) 0.1667(5) 0.0450(12) Uani 1 1 d . . . C9 C 0.9259(5) 0.2756(5) 0.1058(5) 0.0446(13) Uani 1 1 d . . . Cl1 Cl 0.7156(5) 0.3838(5) 0.1343(3) 0.044(5) Uani 1 1 d . . . C4 C 1.0192(4) 0.3697(4) 0.1956(5) 0.0371(15) Uani 1 1 d . . . C11 C 0.7510(5) 0.2654(5) -0.1218(5) 0.0406(11) Uani 1 1 d . . . H11A H 0.8232 0.3373 -0.1106 0.040 Uiso 1 1 calc R . . H11B H 0.7194 0.2130 -0.1946 0.040 Uiso 1 1 calc R . . C1 C 0.9193(4) 0.5722(5) 0.4210(4) 0.0437(12) Uani 1 1 d . . . H1A H 0.9438 0.5856 0.4930 0.040 Uiso 1 1 calc R . . H1B H 0.9389 0.6463 0.4194 0.040 Uiso 1 1 calc R . . OW5 O 0.2248(4) 0.1534(5) 0.4257(5) 0.0441(13) Uani 1 1 d . . . C24 C 0.7210(5) 0.6213(5) 0.3451(5) 0.0454(13) Uani 1 1 d . . . H24A H 0.6884 0.6680 0.3748 0.040 Uiso 1 1 calc R . . H24B H 0.8038 0.6740 0.3513 0.040 Uiso 1 1 calc R . . C25 C 0.6340(6) 0.6089(6) 0.1750(5) 0.0424(15) Uani 1 1 d . . . H25A H 0.5990 0.6521 0.2070 0.036 Uiso 1 1 calc R . . H25B H 0.5771 0.5531 0.1057 0.036 Uiso 1 1 calc R . . C23 C 0.7220(4) 0.5511(4) 0.4038(5) 0.046(5) Uani 1 1 d . . . H23A H 0.7606 0.6022 0.4772 0.036 Uiso 1 1 calc R . . H23B H 0.6388 0.4936 0.3922 0.036 Uiso 1 1 calc R . . N5 N 0.6321(5) 0.2307(5) 0.2251(5) 0.0403(13) Uani 1 1 d . . . H5A H 0.6943 0.2189 0.2344 0.053 Uiso 1 1 calc R . . H5B H 0.6479 0.2798 0.1943 0.053 Uiso 1 1 calc R . . C3 C 1.0507(5) 0.4939(4) 0.2161(4) 0.0455(14) Uani 1 1 d . . . H3C H 1.1355 0.5481 0.2597 0.039 Uiso 1 1 calc R . . H3D H 1.0414 0.5007 0.1509 0.039 Uiso 1 1 calc R . . C31 C 0.7958(5) 0.6564(6) 0.0905(5) 0.0435(14) Uani 1 1 d . . . OW6 O 0.3532(5) 0.1456(5) 0.6013(4) 0.0506(13) Uani 1 1 d . . . C22 C 0.5364(4) 0.1843(4) -0.1513(4) 0.0407(13) Uani 1 1 d . . . H22A H 0.5421 0.1174 -0.1547 0.043 Uiso 1 1 calc R . . H22B H 0.5079 0.1745 -0.2216 0.043 Uiso 1 1 calc R . . C20 C 0.3887(5) 0.1537(6) 0.0410(5) 0.0396(15) Uani 1 1 d . . . C21 C 0.4455(4) 0.1865(4) -0.1012(5) 0.0394(14) Uani 1 1 d . . . H21A H 0.4529 0.2618 -0.0813 0.041 Uiso 1 1 calc R . . H21B H 0.3636 0.1268 -0.1488 0.041 Uiso 1 1 calc R . . C30 C 0.9052(5) 0.7344(6) 0.0861(6) 0.0458(14) Uani 1 1 d . . . H30 H 0.9355 0.7092 0.0361 0.044 Uiso 1 1 calc R . . C12 C 0.7468(5) 0.3903(6) 0.4016(5) 0.0442(13) Uani 1 1 d . . . H12A H 0.7419 0.4142 0.4704 0.042 Uiso 1 1 calc R . . H12B H 0.8072 0.3682 0.4035 0.042 Uiso 1 1 calc R . . C2 C 0.9911(5) 0.5299(5) 0.3686(5) 0.0438(16) Uani 1 1 d . . . H2A H 1.0767 0.5807 0.4107 0.042 Uiso 1 1 calc R . . H2B H 0.9653 0.4521 0.3635 0.042 Uiso 1 1 calc R . . C10 C 0.7860(4) 0.2109(4) -0.0588(5) 0.0411(15) Uani 1 1 d . . . H10A H 0.7152 0.1570 -0.0485 0.041 Uiso 1 1 calc R . . H10B H 0.8199 0.1683 -0.0941 0.041 Uiso 1 1 calc R . . OW4 O 0.7636(5) 0.0341(4) 0.6840(5) 0.045(2) Uani 1 1 d . . . C32 C 0.7612(4) 0.5026(5) -0.0628(5) 0.0408(15) Uani 1 1 d . . . H32A H 0.8371 0.5069 -0.0376 0.038 Uiso 1 1 calc R . . H32B H 0.7739 0.5520 -0.0993 0.038 Uiso 1 1 calc R . . C15 C 0.4160(4) 0.1293(5) 0.1259(5) 0.038(2) Uani 1 1 d . . . C27 C 0.8179(5) 0.8100(5) 0.2371(4) 0.0525(18) Uani 1 1 d . . . H27 H 0.7894 0.8358 0.2885 0.046 Uiso 1 1 calc R . . C8 C 0.8945(5) 0.1607(6) 0.0875(5) 0.0465(14) Uani 1 1 d . . . H8 H 0.8332 0.0979 0.0272 0.050 Uiso 1 1 calc R . . C33 C 0.6645(5) 0.3812(4) -0.1326(5) 0.0387(14) Uani 1 1 d . . . H33A H 0.6755 0.3626 -0.1993 0.039 Uiso 1 1 calc R . . H33B H 0.5867 0.3758 -0.1427 0.039 Uiso 1 1 calc R . . C13 C 0.6261(4) 0.2866(5) 0.3278(5) 0.0396(15) Uani 1 1 d . . . H13A H 0.5972 0.2300 0.3567 0.048 Uiso 1 1 calc R . . H13B H 0.5679 0.3108 0.3190 0.048 Uiso 1 1 calc R . . C5 C 1.0823(5) 0.3493(5) 0.2658(6) 0.0359(15) Uani 1 1 d . . . H5 H 1.1474 0.4123 0.3237 0.048 Uiso 1 1 calc R . . C28 C 0.9268(5) 0.8893(4) 0.2319(4) 0.048(2) Uani 1 1 d . . . H28 H 0.9706 0.9675 0.2784 0.054 Uiso 1 1 calc R . . OW2 O 0.4690(4) 0.0130(5) 0.3734(5) 0.053(2) Uani 1 1 d . . . OW1 O 1.0331(5) 0.1036(5) 0.4912(6) 0.0493(14) Uani 1 1 d . . . C18 C 0.2124(4) 0.1514(5) 0.0733(5) 0.0437(13) Uani 1 1 d . . . H18 H 0.1468 0.1607 0.0575 0.052 Uiso 1 1 calc R . . OW7 O 0.4040(5) 0.3468(5) 0.4217(5) 0.042(2) Uani 1 1 d . . . C19 C 0.2894(4) 0.1639(5) 0.0140(5) 0.0449(13) Uani 1 1 d . . . H19 H 0.2735 0.1790 -0.0432 0.047 Uiso 1 1 calc R . . OW9 O 0.4138(6) 0.4266(6) 0.2347(6) 0.055(2) Uani 1 1 d . . . OW8 O 0.5975(5) 0.4324(5) 0.5914(5) 0.044(2) Uani 1 1 d . . . C6 C 1.0496(5) 0.2365(4) 0.2509(5) 0.054(2) Uani 1 1 d . . . H6 H 1.0893 0.2233 0.3002 0.065 Uiso 1 1 calc R . . C14 C 0.5177(5) 0.1168(6) 0.1549(5) 0.047(2) Uani 1 1 d . . . H14A H 0.5311 0.0810 0.0930 0.057 Uiso 1 1 calc R . . H14B H 0.4984 0.0651 0.1893 0.057 Uiso 1 1 calc R . . C16 C 0.3353(5) 0.1132(5) 0.1811(6) 0.039(3) Uani 1 1 d . . . H16 H 0.3486 0.0942 0.2362 0.067 Uiso 1 1 calc R . . C7 C 0.9554(5) 0.1425(5) 0.1598(5) 0.047(3) Uani 1 1 d . . . H7 H 0.9340 0.0668 0.1484 0.074 Uiso 1 1 calc R . . C17 C 0.2366(4) 0.1246(4) 0.1565(4) 0.043(3) Uani 1 1 d . . . H17 H 0.1855 0.1144 0.1957 0.069 Uiso 1 1 calc R . . C29 C 0.9677(4) 0.8482(5) 0.1557(5) 0.048(2) Uani 1 1 d . . . H29 H 1.0406 0.9001 0.1518 0.057 Uiso 1 1 calc R . . OW3 O 0.8576(5) 0.2221(6) 0.6387(5) 0.050(4) Uani 1 1 d . . . OW10 O 0.7721(5) 0.1489(5) 0.2696(5) 0.042(4) Uani 1 1 d . . . Cl3 Cl 0.8059(5) 0.0811(4) 0.4296(4) 0.043(4) 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 Cl2 0.051(3) 0.040(3) 0.023(2) 0.011(2) 0.007(2) 0.003(2) O1 0.041(3) 0.030(3) 0.024(2) 0.010(2) 0.006(2) 0.001(2) O2 0.042(3) 0.033(3) 0.025(3) 0.011(2) 0.005(2) 0.002(2) O3 0.046(3) 0.033(3) 0.026(3) 0.011(2) 0.007(2) 0.001(3) N1 0.038(3) 0.033(3) 0.025(3) 0.014(3) 0.008(3) 0.002(3) N2 0.047(4) 0.028(3) 0.018(3) 0.017(2) 0.008(3) 0.003(3) N3 0.043(4) 0.040(4) 0.029(4) 0.019(3) 0.006(3) 0.002(4) N4 0.039(3) 0.031(3) 0.024(3) 0.009(2) 0.004(3) 0.003(3) C26 0.046(4) 0.030(4) 0.035(4) 0.020(3) 0.005(3) 0.001(4) C9 0.036(4) 0.035(4) 0.037(4) 0.014(3) 0.006(3) 0.002(4) Cl1 0.041(4) 0.036(4) 0.030(4) 0.013(3) 0.004(3) 0.004(3) C4 0.039(4) 0.032(4) 0.022(4) 0.015(3) 0.010(3) 0.004(3) C11 0.043(4) 0.031(4) 0.028(4) 0.015(3) 0.007(3) 0.004(4) C1 0.040(4) 0.037(4) 0.026(4) 0.014(3) 0.003(3) 0.001(4) OW5 0.045(4) 0.032(4) 0.030(4) 0.015(3) 0.007(3) 0.001(3) C24 0.042(4) 0.035(4) 0.030(4) 0.013(3) 0.008(3) 0.002(3) C25 0.040(4) 0.038(4) 0.022(3) 0.011(3) 0.005(3) 0.003(4) C23 0.043(4) 0.036(4) 0.030(4) 0.013(3) 0.006(3) 0.002(3) N5 0.043(5) 0.029(3) 0.023(3) 0.007(3) 0.004(3) 0.001(3) C3 0.044(4) 0.034(4) 0.031(4) 0.015(3) 0.007(3) 0.003(3) C31 0.045(4) 0.028(4) 0.031(4) 0.011(3) 0.005(3) 0.001(3) OW6 0.049(5) 0.036(5) 0.035(5) 0.015(4) 0.007(4) 0.003(4) C22 0.038(4) 0.030(4) 0.027(4) 0.007(3) 0.007(3) 0.002(3) C20 0.044(5) 0.031(4) 0.029(4) 0.018(3) 0.006(4) 0.003(4) C21 0.043(4) 0.033(4) 0.026(4) 0.014(3) 0.006(3) 0.004(4) C30 0.048(4) 0.033(4) 0.030(4) 0.017(3) 0.005(4) 0.002(4) C12 0.053(5) 0.028(4) 0.022(3) 0.011(3) 0.006(3) 0.002(3) C2 0.041(4) 0.031(4) 0.035(4) 0.014(3) 0.007(3) 0.003(4) C10 0.036(4) 0.031(4) 0.035(4) 0.013(3) 0.010(3) 0.004(3) OW4 0.050(5) 0.035(5) 0.030(5) 0.021(4) 0.011(4) 0.004(4) C32 0.039(4) 0.032(4) 0.024(3) 0.007(3) 0.013(3) 0.001(3) C15 0.042(5) 0.029(4) 0.021(4) 0.011(3) 0.007(4) 0.004(4) C27 0.057(5) 0.040(4) 0.030(4) 0.017(4) 0.005(4) 0.003(4) C8 0.043(4) 0.027(4) 0.042(4) 0.013(4) -0.003(4) 0.003(4) C33 0.042(4) 0.030(4) 0.022(4) 0.016(3) 0.010(3) 0.004(4) C13 0.046(5) 0.029(4) 0.024(4) 0.016(3) 0.007(4) 0.003(4) C5 0.038(4) 0.030(4) 0.020(4) 0.013(4) 0.007(4) 0.003(4) C28 0.042(6) 0.034(4) 0.039(4) 0.017(4) 0.005(4) 0.001(4) OW2 0.051(5) 0.039(5) 0.035(5) 0.014(4) 0.007(4) 0.002(4) OW1 0.052(4) 0.036(4) 0.030(4) 0.015(3) 0.011(3) 0.001(4) C18 0.046(5) 0.034(4) 0.025(4) 0.012(3) 0.010(4) 0.002(4) OW7 0.045(5) 0.032(5) 0.025(5) 0.014(4) 0.007(4) 0.003(4) C19 0.045(5) 0.031(4) 0.036(4) 0.015(3) 0.006(4) 0.004(4) OW9 0.058(4) 0.037(4) 0.035(4) 0.015(3) 0.005(3) 0.003(3) OW8 0.046(5) 0.031(5) 0.030(4) 0.016(4) 0.007(4) 0.002(4) C6 0.055(6) 0.038(5) 0.034(5) 0.011(4) 0.006(4) 0.004(5) C14 0.049(6) 0.032(4) 0.030(4) 0.008(3) 0.005(4) 0.004(4) C16 0.044(4) 0.029(4) 0.024(4) 0.015(4) 0.007(3) 0.003(4) C7 0.044(5) 0.033(5) 0.030(6) 0.011(4) -0.003(4) 0.002(4) C17 0.045(6) 0.034(5) 0.021(5) 0.012(4) 0.006(5) 0.004(5) C29 0.050(5) 0.033(5) 0.027(5) 0.013(4) 0.010(4) 0.001(4) OW3 0.054(5) 0.035(4) 0.030(5) 0.012(4) 0.006(4) 0.003(4) OW10 0.045(4) 0.032(4) 0.025(4) 0.016(3) 0.006(3) 0.002(3) Cl3 0.046(4) 0.036(4) 0.023(3) 0.012(3) 0.011(3) 0.003(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 C9 1.358(8) . ? O1 C10 1.409(9) . ? O2 C31 1.374(8) . ? O2 C32 1.443(7) . ? O3 C20 1.374(9) . ? O3 C21 1.438(8) . ? N1 C11 1.469(9) . ? N1 C22 1.481(9) . ? N1 C33 1.498(8) . ? N2 C1 1.464(9) . ? N2 C23 1.483(8) . ? N2 C12 1.486(8) . ? N3 C3 1.447(9) . ? N3 C2 1.459(9) . ? N3 H3A 0.9000 . ? N3 H3B 0.9000 . ? N4 C25 1.449(8) . ? N4 C24 1.493(9) . ? N4 H4A 0.9000 . ? N4 H4B 0.9000 . ? C26 C27 1.395(10) . ? C26 C31 1.398(9) . ? C26 C25 1.505(10) . ? C9 C4 1.395(10) . ? C9 C8 1.410(10) . ? C4 C5 1.388(10) . ? C4 C3 1.531(10) . ? C11 C10 1.500(10) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C1 C2 1.505(9) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C24 C23 1.493(9) . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? N5 C13 1.487(10) . ? N5 C14 1.496(10) . ? N5 H5A 0.9000 . ? N5 H5B 0.9000 . ? C3 H3C 0.9700 . ? C3 H3D 0.9700 . ? C31 C30 1.386(10) . ? C22 C21 1.491(10) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C20 C19 1.382(12) . ? C20 C15 1.409(10) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C30 C29 1.361(11) . ? C30 H30 0.9300 . ? C12 C13 1.494(11) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C32 C33 1.473(10) . ? C32 H32A 0.9700 . ? C32 H32B 0.9700 . ? C15 C16 1.398(12) . ? C15 C14 1.435(12) . ? C27 C28 1.393(11) . ? C27 H27 0.9300 . ? C8 C7 1.371(11) . ? C8 H8 0.9300 . ? C33 H33A 0.9700 . ? C33 H33B 0.9700 . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C5 C6 1.390(11) . ? C5 H5 0.9300 . ? C28 C29 1.381(11) . ? C28 H28 0.9300 . ? C18 C17 1.399(11) . ? C18 C19 1.406(10) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C6 C7 1.409(12) . ? C6 H6 0.9300 . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C16 C17 1.378(14) . ? C16 H16 0.9300 . ? C7 H7 0.9300 . ? C17 H17 0.9300 . ? C29 H29 0.9300 . ? 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 C9 O1 C10 118.7(5) . . ? C31 O2 C32 116.3(5) . . ? C20 O3 C21 116.7(6) . . ? C11 N1 C22 109.7(5) . . ? C11 N1 C33 108.0(5) . . ? C22 N1 C33 108.6(5) . . ? C1 N2 C23 110.6(5) . . ? C1 N2 C12 111.5(5) . . ? C23 N2 C12 109.9(5) . . ? C3 N3 C2 113.7(6) . . ? C3 N3 H3A 108.8 . . ? C2 N3 H3A 108.8 . . ? C3 N3 H3B 108.8 . . ? C2 N3 H3B 108.8 . . ? H3A N3 H3B 107.7 . . ? C25 N4 C24 113.6(5) . . ? C25 N4 H4A 108.8 . . ? C24 N4 H4A 108.8 . . ? C25 N4 H4B 108.8 . . ? C24 N4 H4B 108.8 . . ? H4A N4 H4B 107.7 . . ? C27 C26 C31 118.1(7) . . ? C27 C26 C25 120.2(6) . . ? C31 C26 C25 121.7(6) . . ? O1 C9 C4 116.4(6) . . ? O1 C9 C8 123.2(7) . . ? C4 C9 C8 120.3(7) . . ? C5 C4 C9 119.4(7) . . ? C5 C4 C3 120.6(7) . . ? C9 C4 C3 120.0(6) . . ? N1 C11 C10 112.9(6) . . ? N1 C11 H11A 109.0 . . ? C10 C11 H11A 109.0 . . ? N1 C11 H11B 109.0 . . ? C10 C11 H11B 109.0 . . ? H11A C11 H11B 107.8 . . ? N2 C1 C2 113.5(6) . . ? N2 C1 H1A 108.9 . . ? C2 C1 H1A 108.9 . . ? N2 C1 H1B 108.9 . . ? C2 C1 H1B 108.9 . . ? H1A C1 H1B 107.7 . . ? N4 C24 C23 111.6(6) . . ? N4 C24 H24A 109.3 . . ? C23 C24 H24A 109.3 . . ? N4 C24 H24B 109.3 . . ? C23 C24 H24B 109.3 . . ? H24A C24 H24B 108.0 . . ? N4 C25 C26 115.2(6) . . ? N4 C25 H25A 108.5 . . ? C26 C25 H25A 108.5 . . ? N4 C25 H25B 108.5 . . ? C26 C25 H25B 108.5 . . ? H25A C25 H25B 107.5 . . ? N2 C23 C24 112.6(5) . . ? N2 C23 H23A 109.1 . . ? C24 C23 H23A 109.1 . . ? N2 C23 H23B 109.1 . . ? C24 C23 H23B 109.1 . . ? H23A C23 H23B 107.8 . . ? C13 N5 C14 113.4(7) . . ? C13 N5 H5A 108.9 . . ? C14 N5 H5A 108.9 . . ? C13 N5 H5B 108.9 . . ? C14 N5 H5B 108.9 . . ? H5A N5 H5B 107.7 . . ? N3 C3 C4 113.7(5) . . ? N3 C3 H3C 108.8 . . ? C4 C3 H3C 108.8 . . ? N3 C3 H3D 108.8 . . ? C4 C3 H3D 108.8 . . ? H3C C3 H3D 107.7 . . ? O2 C31 C30 124.4(6) . . ? O2 C31 C26 114.8(6) . . ? C30 C31 C26 120.8(7) . . ? N1 C22 C21 113.4(6) . . ? N1 C22 H22A 108.9 . . ? C21 C22 H22A 108.9 . . ? N1 C22 H22B 108.9 . . ? C21 C22 H22B 108.9 . . ? H22A C22 H22B 107.7 . . ? O3 C20 C19 124.1(6) . . ? O3 C20 C15 113.4(7) . . ? C19 C20 C15 122.5(7) . . ? O3 C21 C22 107.5(6) . . ? O3 C21 H21A 110.2 . . ? C22 C21 H21A 110.2 . . ? O3 C21 H21B 110.2 . . ? C22 C21 H21B 110.2 . . ? H21A C21 H21B 108.5 . . ? C29 C30 C31 119.4(7) . . ? C29 C30 H30 120.3 . . ? C31 C30 H30 120.3 . . ? N2 C12 C13 112.9(6) . . ? N2 C12 H12A 109.0 . . ? C13 C12 H12A 109.0 . . ? N2 C12 H12B 109.0 . . ? C13 C12 H12B 109.0 . . ? H12A C12 H12B 107.8 . . ? N3 C2 C1 112.7(6) . . ? N3 C2 H2A 109.0 . . ? C1 C2 H2A 109.0 . . ? N3 C2 H2B 109.0 . . ? C1 C2 H2B 109.0 . . ? H2A C2 H2B 107.8 . . ? O1 C10 C11 107.4(6) . . ? O1 C10 H10A 110.2 . . ? C11 C10 H10A 110.2 . . ? O1 C10 H10B 110.2 . . ? C11 C10 H10B 110.2 . . ? H10A C10 H10B 108.5 . . ? O2 C32 C33 107.6(5) . . ? O2 C32 H32A 110.2 . . ? C33 C32 H32A 110.2 . . ? O2 C32 H32B 110.2 . . ? C33 C32 H32B 110.2 . . ? H32A C32 H32B 108.5 . . ? C16 C15 C20 116.4(8) . . ? C16 C15 C14 120.0(8) . . ? C20 C15 C14 123.6(8) . . ? C28 C27 C26 121.4(7) . . ? C28 C27 H27 119.3 . . ? C26 C27 H27 119.3 . . ? C7 C8 C9 119.2(7) . . ? C7 C8 H8 120.4 . . ? C9 C8 H8 120.4 . . ? C32 C33 N1 115.4(6) . . ? C32 C33 H33A 108.4 . . ? N1 C33 H33A 108.4 . . ? C32 C33 H33B 108.4 . . ? N1 C33 H33B 108.4 . . ? H33A C33 H33B 107.5 . . ? N5 C13 C12 112.3(6) . . ? N5 C13 H13A 109.2 . . ? C12 C13 H13A 109.2 . . ? N5 C13 H13B 109.2 . . ? C12 C13 H13B 109.2 . . ? H13A C13 H13B 107.9 . . ? C4 C5 C6 121.1(8) . . ? C4 C5 H5 119.5 . . ? C6 C5 H5 119.5 . . ? C29 C28 C27 118.1(7) . . ? C29 C28 H28 121.0 . . ? C27 C28 H28 121.0 . . ? C17 C18 C19 118.6(9) . . ? C17 C18 H18 120.7 . . ? C19 C18 H18 120.7 . . ? C20 C19 C18 119.7(7) . . ? C20 C19 H19 120.1 . . ? C18 C19 H19 120.1 . . ? C5 C6 C7 118.7(8) . . ? C5 C6 H6 120.7 . . ? C7 C6 H6 120.7 . . ? C15 C14 N5 112.8(6) . . ? C15 C14 H14A 109.0 . . ? N5 C14 H14A 109.0 . . ? C15 C14 H14B 109.0 . . ? N5 C14 H14B 109.0 . . ? H14A C14 H14B 107.8 . . ? C17 C16 C15 122.1(8) . . ? C17 C16 H16 118.9 . . ? C15 C16 H16 118.9 . . ? C8 C7 C6 121.3(8) . . ? C8 C7 H7 119.4 . . ? C6 C7 H7 119.4 . . ? C16 C17 C18 120.7(8) . . ? C16 C17 H17 119.7 . . ? C18 C17 H17 119.7 . . ? C30 C29 C28 122.3(8) . . ? C30 C29 H29 118.8 . . ? C28 C29 H29 118.8 . . ? 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 C10 O1 C9 C4 174.7(6) . . . . ? C10 O1 C9 C8 -2.1(10) . . . . ? O1 C9 C4 C5 -175.6(6) . . . . ? C8 C9 C4 C5 1.3(10) . . . . ? O1 C9 C4 C3 4.6(9) . . . . ? C8 C9 C4 C3 -178.5(6) . . . . ? C22 N1 C11 C10 -82.0(7) . . . . ? C33 N1 C11 C10 159.7(6) . . . . ? C23 N2 C1 C2 -161.1(5) . . . . ? C12 N2 C1 C2 76.2(7) . . . . ? C25 N4 C24 C23 175.0(6) . . . . ? C24 N4 C25 C26 64.7(7) . . . . ? C27 C26 C25 N4 -94.2(8) . . . . ? C31 C26 C25 N4 84.9(8) . . . . ? C1 N2 C23 C24 78.1(7) . . . . ? C12 N2 C23 C24 -158.4(6) . . . . ? N4 C24 C23 N2 67.5(8) . . . . ? C2 N3 C3 C4 63.6(8) . . . . ? C5 C4 C3 N3 -94.6(8) . . . . ? C9 C4 C3 N3 85.2(8) . . . . ? C32 O2 C31 C30 -4.5(10) . . . . ? C32 O2 C31 C26 174.6(6) . . . . ? C27 C26 C31 O2 -178.2(6) . . . . ? C25 C26 C31 O2 2.7(10) . . . . ? C27 C26 C31 C30 0.9(10) . . . . ? C25 C26 C31 C30 -178.1(7) . . . . ? C11 N1 C22 C21 157.0(6) . . . . ? C33 N1 C22 C21 -85.2(7) . . . . ? C21 O3 C20 C19 -1.7(10) . . . . ? C21 O3 C20 C15 178.0(6) . . . . ? C20 O3 C21 C22 -174.4(6) . . . . ? N1 C22 C21 O3 -75.8(7) . . . . ? O2 C31 C30 C29 177.7(7) . . . . ? C26 C31 C30 C29 -1.4(11) . . . . ? C1 N2 C12 C13 -159.2(6) . . . . ? C23 N2 C12 C13 77.8(7) . . . . ? C3 N3 C2 C1 176.1(6) . . . . ? N2 C1 C2 N3 68.7(8) . . . . ? C9 O1 C10 C11 -175.6(6) . . . . ? N1 C11 C10 O1 -82.1(7) . . . . ? C31 O2 C32 C33 -173.4(6) . . . . ? O3 C20 C15 C16 -178.4(6) . . . . ? C19 C20 C15 C16 1.3(11) . . . . ? O3 C20 C15 C14 -0.5(10) . . . . ? C19 C20 C15 C14 179.3(7) . . . . ? C31 C26 C27 C28 0.2(11) . . . . ? C25 C26 C27 C28 179.3(7) . . . . ? O1 C9 C8 C7 177.7(8) . . . . ? C4 C9 C8 C7 1.0(12) . . . . ? O2 C32 C33 N1 -76.1(7) . . . . ? C11 N1 C33 C32 -81.4(7) . . . . ? C22 N1 C33 C32 159.7(6) . . . . ? C14 N5 C13 C12 171.3(6) . . . . ? N2 C12 C13 N5 69.7(8) . . . . ? C9 C4 C5 C6 -3.6(11) . . . . ? C3 C4 C5 C6 176.1(7) . . . . ? C26 C27 C28 C29 -1.0(12) . . . . ? O3 C20 C19 C18 -179.4(7) . . . . ? C15 C20 C19 C18 0.9(11) . . . . ? C17 C18 C19 C20 -2.2(11) . . . . ? C4 C5 C6 C7 3.7(13) . . . . ? C16 C15 C14 N5 -95.4(8) . . . . ? C20 C15 C14 N5 86.8(9) . . . . ? C13 N5 C14 C15 65.4(8) . . . . ? C20 C15 C16 C17 -2.2(12) . . . . ? C14 C15 C16 C17 179.7(8) . . . . ? C9 C8 C7 C6 -0.9(14) . . . . ? C5 C6 C7 C8 -1.4(15) . . . . ? C15 C16 C17 C18 1.0(13) . . . . ? C19 C18 C17 C16 1.3(12) . . . . ? C31 C30 C29 C28 0.7(13) . . . . ? C27 C28 C29 C30 0.5(13) . . . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 28.40 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.730 _refine_diff_density_min -0.435 _refine_diff_density_rms 0.176 data_Complex2 #TrackingRef 'B924157D_ccdc_754955_754960_cif.txt' _database_code_depnum_ccdc_archive 'CCDC 754956' #TrackingRef 'Complex1-6.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C33 H57 Cl4 N5 O23' _chemical_formula_sum 'C33 H57 Cl4 N5 O23 S0' _chemical_formula_weight 1033.64 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 Monoclinic _symmetry_space_group_name_H-M P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 15.007(5) _cell_length_b 14.443(3) _cell_length_c 21.342(6) _cell_angle_alpha 90.00 _cell_angle_beta 95.480(5) _cell_angle_gamma 90.00 _cell_volume 4605(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(1) _cell_measurement_reflns_used ? _cell_measurement_theta_min 2.0 _cell_measurement_theta_max 28.5 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.491 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2168 _exptl_absorpt_coefficient_mu 0.345 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9342 _exptl_absorpt_correction_T_max 0.9469 _exptl_absorpt_process_details 'SADABAS 2.10 (Bruker 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(1) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX' _diffrn_measurement_method /w-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 30683 _diffrn_reflns_av_R_equivalents 0.0648 _diffrn_reflns_av_sigmaI/netI 0.0754 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.96 _diffrn_reflns_theta_max 28.45 _reflns_number_total 21797 _reflns_number_gt 13807 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART 5.628 (Bruker, 2003)' _computing_cell_refinement 'SAINT 6.45 ( Bruker, 2003)' _computing_data_reduction 'SAINT 6.45 (Bruker, 2003)' _computing_structure_solution SIR-97 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Diamond 2.1e' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0400P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.08(8) _refine_ls_number_reflns 21797 _refine_ls_number_parameters 1181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1006 _refine_ls_R_factor_gt 0.0711 _refine_ls_wR_factor_ref 0.2326 _refine_ls_wR_factor_gt 0.1806 _refine_ls_goodness_of_fit_ref 1.088 _refine_ls_restrained_S_all 1.088 _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 Cl6 Cl 1.35138(5) 0.73070(5) 0.61853(5) 0.0296(4) Uani 1 1 d . . . Cl5 Cl 1.44502(3) 0.57209(4) 0.81927(3) 0.0297(4) Uani 1 1 d . . . Cl1 Cl 1.61037(4) 0.19237(5) 0.69351(5) 0.0345(4) Uani 1 1 d . . . Cl3 Cl 1.15776(5) 0.14212(5) 0.50603(5) 0.0389(5) Uani 1 1 d . . . Cl2 Cl 1.58688(4) -0.10437(5) 0.94442(5) 0.0364(5) Uani 1 1 d . . . Cl4 Cl 1.89803(5) 0.38841(5) 0.80637(4) 0.0463(5) Uani 1 1 d . . . Cl7 Cl 1.1363(3) 0.7508(3) 0.8976(2) 0.0469(6) Uani 1 1 d . . . Cl8 Cl 1.0948(3) 0.8952(4) 0.7187(2) 0.0390(6) Uani 1 1 d . . . O5 O 1.3955(4) 0.0511(4) 0.9058(2) 0.0285(5) Uani 1 1 d . . . O4 O 1.3593(4) 0.1615(4) 0.7024(3) 0.0352(5) Uani 1 1 d . . . O10 O 1.6032(5) -0.0123(4) 0.9183(3) 0.0393(6) Uani 1 1 d . . . O20 O 1.9391(4) 0.4070(5) 0.7481(3) 0.0399(6) Uani 1 1 d . . . O30 O 1.4121(4) 0.7291(5) 0.6740(3) 0.0381(5) Uani 1 1 d . . . O25 O 1.4330(5) 0.5135(4) 0.8727(3) 0.0341(5) Uani 1 1 d . . . O2 O 2.1518(4) 0.4341(5) 0.7650(3) 0.0419(6) Uani 1 1 d . . . O12 O 1.5820(5) 0.1531(5) 0.7505(3) 0.0431(6) Uani 1 1 d . . . O1 O 2.0893(4) 0.4901(4) 0.5551(3) 0.0331(13) Uani 1 1 d . . . O13 O 1.5677(5) 0.1440(4) 0.6398(3) 0.040(6) Uani 1 1 d . . . O28 O 1.3451(4) 0.8249(4) 0.5948(3) 0.0401(14) Uani 1 1 d . . . O27 O 1.3829(4) 0.6708(4) 0.5714(3) 0.0374(14) Uani 1 1 d . . . O24 O 1.5006(4) 0.5215(4) 0.7786(3) 0.0337(13) Uani 1 1 d . . . O7 O 1.5520(5) -0.0930(4) 1.0030(3) 0.0406(15) Uani 1 1 d . . . O16 O 1.1377(5) 0.1158(5) 0.5681(3) 0.0515(12) Uani 1 1 d . . . O14 O 1.5836(4) 0.2884(4) 0.6898(3) 0.0405(14) Uani 1 1 d . . . O26 O 1.4862(4) 0.6566(4) 0.8389(3) 0.0379(14) Uani 1 1 d . . . O9 O 1.6685(5) -0.1536(5) 0.9533(3) 0.0484(12) Uani 1 1 d . . . N8 N 1.4812(5) 0.3259(5) 0.7967(3) 0.0302(14) Uani 1 1 d . . . H8A H 1.5104 0.2965 0.7676 0.036 Uiso 1 1 calc R . . H8B H 1.4959 0.3863 0.7958 0.036 Uiso 1 1 calc R . . O6 O 1.6240(4) -0.0833(4) 0.7726(3) 0.0381(14) Uani 1 1 d . . . N7 N 1.6481(4) 0.2277(5) 0.9188(3) 0.0328(15) Uani 1 1 d . . . H7 H 1.6207 0.1728 0.9087 0.039 Uiso 1 1 calc R . . O11 O 1.7066(4) 0.1880(5) 0.6936(3) 0.0460(13) Uani 1 1 d . . . O18 O 1.1580(5) 0.2383(5) 0.5006(4) 0.0361(12) Uani 1 1 d . . . O8 O 1.5242(5) -0.1526(4) 0.9007(3) 0.0464(11) Uani 1 1 d . . . O29 O 1.2643(4) 0.7002(5) 0.6326(3) 0.0436(15) Uani 1 1 d . . . O3 O 1.8361(4) 0.6326(4) 0.6946(3) 0.0373(14) Uani 1 1 d . . . O23 O 1.3597(4) 0.5894(5) 0.7857(3) 0.0381(14) Uani 1 1 d . . . N6 N 1.4049(3) -0.0429(3) 0.7457(3) 0.0315(15) Uani 1 1 d . . . O17 O 1.2435(3) 0.1065(5) 0.4950(4) 0.0368(12) Uani 1 1 d . . . N1 N 1.8592(5) 0.3388(5) 0.5675(5) 0.0317(15) Uani 1 1 d . . . H1 H 1.8927 0.3914 0.5695 0.038 Uiso 1 1 calc R . . N2 N 2.0662(4) 0.6162(4) 0.7062(3) 0.0389(13) Uani 1 1 d . . . C48 C 1.3768(5) 0.0933(5) 1.0101(4) 0.0269(13) Uani 1 1 d . . . OW2 O 1.4521(5) 0.7690(5) 0.4688(3) 0.0497(12) Uani 1 1 d . . . N5 N 1.6837(4) 0.4531(5) 0.6520(4) 0.0338(15) Uani 1 1 d . . . H5A H 1.6723 0.4003 0.6723 0.041 Uiso 1 1 calc R . . H5B H 1.6406 0.4598 0.6200 0.041 Uiso 1 1 calc R . . N3 N 1.9354(5) 0.4340(5) 0.4603(3) 0.0352(12) Uani 1 1 d . . . H3A H 1.9400 0.4601 0.4988 0.042 Uiso 1 1 calc R . . H3B H 1.9258 0.4799 0.4320 0.042 Uiso 1 1 calc R . . C9 C 2.1334(5) 0.5024(5) 0.5044(4) 0.0287(12) Uani 1 1 d . . . C59 C 1.3604(4) 0.3250(5) 0.7087(4) 0.0313(12) Uani 1 1 d . . . C32 C 1.9997(5) 0.2782(5) 0.6245(4) 0.0370(13) Uani 1 1 d . . . H32A H 2.0236 0.2310 0.5985 0.044 Uiso 1 1 calc R . . H32B H 2.0187 0.3382 0.6102 0.044 Uiso 1 1 calc R . . N10 N 1.7538(5) 0.0671(5) 0.8609(4) 0.0389(15) Uani 1 1 d . . . H10A H 1.6951 0.0576 0.8638 0.047 Uiso 1 1 calc R . . H10B H 1.7838 0.0439 0.8960 0.047 Uiso 1 1 calc R . . C37 C 1.7750(3) -0.0868(3) 0.8117(4) 0.042(2) Uani 1 1 d . . . O15 O 1.0901(4) 0.1033(5) 0.4611(4) 0.056(2) Uani 1 1 d . . . C63 C 1.3433(5) 0.2523(5) 0.6054(4) 0.0338(13) Uani 1 1 d . . . H63 H 1.3389 0.1997 0.5801 0.041 Uiso 1 1 calc R . . N9 N 1.5421(4) 0.1121(5) 1.0077(3) 0.0284(14) Uani 1 1 d . . . H9A H 1.5437 0.0625 1.0333 0.034 Uiso 1 1 calc R . . H9B H 1.5465 0.0913 0.9683 0.034 Uiso 1 1 calc R . . C19 C 1.6828(5) 0.6250(5) 0.6637(4) 0.0305(12) Uani 1 1 d . . . C58 C 1.3799(5) 0.3160(4) 0.7792(4) 0.0315(13) Uani 1 1 d . . . H58A H 1.3597 0.2561 0.7928 0.038 Uiso 1 1 calc R . . H58B H 1.3481 0.3637 0.8001 0.038 Uiso 1 1 calc R . . C66 C 1.3286(5) -0.0029(4) 0.7040(4) 0.0357(13) Uani 1 1 d . . . H66A H 1.3047 -0.0518 0.6761 0.043 Uiso 1 1 calc R . . H66B H 1.2820 0.0136 0.7305 0.043 Uiso 1 1 calc R . . O22 O 1.8050(5) 0.3766(5) 0.7911(5) 0.033(3) Uani 1 1 d . . . C52 C 1.2769(3) -0.0197(3) 0.9604(4) 0.0337(15) Uani 1 1 d . . . H52 H 1.2588 -0.0565 0.9258 0.040 Uiso 1 1 calc R . . C53 C 1.3481(5) 0.0395(5) 0.9576(4) 0.0293(16) Uani 1 1 d . . . C57 C 1.5112(5) 0.2877(5) 0.8600(4) 0.0307(14) Uani 1 1 d . . . H57A H 1.4951 0.2227 0.8616 0.037 Uiso 1 1 calc R . . H57B H 1.4814 0.3202 0.8918 0.037 Uiso 1 1 calc R . . C11 C 2.0488(5) 0.5421(5) 0.6555(4) 0.039(2) Uani 1 1 d . . . H11A H 2.0538 0.4811 0.6745 0.047 Uiso 1 1 calc R . . H11B H 1.9886 0.5489 0.6350 0.047 Uiso 1 1 calc R . . C13 C 1.9150(5) 0.6887(5) 0.7002(5) 0.041(2) Uani 1 1 d . . . H13A H 1.9035 0.7471 0.7203 0.050 Uiso 1 1 calc R . . H13B H 1.9342 0.7015 0.6589 0.050 Uiso 1 1 calc R . . O19 O 1.9365(4) 0.3042(5) 0.8333(5) 0.045(3) Uani 1 1 d . . . C62 C 1.3387(4) 0.3392(5) 0.5785(4) 0.038(2) Uani 1 1 d . . . H62 H 1.3306 0.3446 0.5349 0.045 Uiso 1 1 calc R . . C60 C 1.3563(3) 0.4099(3) 0.6805(4) 0.0358(14) Uani 1 1 d . . . H60 H 1.3607 0.4627 0.7056 0.043 Uiso 1 1 calc R . . N4 N 2.0350(5) 0.2643(5) 0.6910(4) 0.0383(15) Uani 1 1 d . . . H4A H 2.0146 0.2100 0.7046 0.046 Uiso 1 1 calc R . . H4B H 2.0140 0.3096 0.7146 0.046 Uiso 1 1 calc R . . C56 C 1.6124(5) 0.2979(4) 0.8740(4) 0.0332(15) Uani 1 1 d . . . H56A H 1.6407 0.2918 0.8352 0.040 Uiso 1 1 calc R . . H56B H 1.6262 0.3590 0.8911 0.040 Uiso 1 1 calc R . . C4 C 2.0973(5) 0.4558(4) 0.4497(4) 0.0366(14) Uani 1 1 d . . . C64 C 1.3548(5) 0.2438(5) 0.6708(4) 0.0309(13) Uani 1 1 d . . . C8 C 2.2096(4) 0.5562(5) 0.5019(5) 0.040(2) Uani 1 1 d . . . H8 H 2.2350 0.5854 0.5382 0.048 Uiso 1 1 calc R . . C55 C 1.4317(4) 0.0136(5) 0.8034(4) 0.0319(11) Uani 1 1 d . . . H55A H 1.4298 0.0790 0.7929 0.038 Uiso 1 1 calc R . . H55B H 1.4924 -0.0018 0.8198 0.038 Uiso 1 1 calc R . . C23 C 2.1504(5) 0.5986(4) 0.7491(4) 0.032(2) Uani 1 1 d . . . H23A H 2.1986 0.5875 0.7228 0.051 Uiso 1 1 calc R . . H23B H 2.1649 0.6550 0.7725 0.051 Uiso 1 1 calc R . . C49 C 1.3324(4) 0.0866(5) 1.0641(4) 0.0342(12) Uani 1 1 d . . . H49 H 1.3518 0.1218 1.0992 0.041 Uiso 1 1 calc R . . C21 C 1.7705(5) 0.4428(4) 0.6254(4) 0.0310(13) Uani 1 1 d . . . H21A H 1.8176 0.4339 0.6593 0.037 Uiso 1 1 calc R . . H21B H 1.7837 0.4990 0.6031 0.037 Uiso 1 1 calc R . . C22 C 1.7690(5) 0.3618(5) 0.5809(5) 0.0363(13) Uani 1 1 d . . . H22A H 1.7419 0.3088 0.5996 0.044 Uiso 1 1 calc R . . H22B H 1.7331 0.3771 0.5420 0.044 Uiso 1 1 calc R . . C51 C 1.2309(4) -0.0258(4) 1.0147(5) 0.0314(13) Uani 1 1 d . . . H51 H 1.1822 -0.0654 1.0154 0.045 Uiso 1 1 calc R . . C20 C 1.6772(5) 0.5327(4) 0.6969(4) 0.0345(13) Uani 1 1 d . . . H20A H 1.7254 0.5284 0.7305 0.041 Uiso 1 1 calc R . . H20B H 1.6210 0.5290 0.7157 0.041 Uiso 1 1 calc R . . C46 C 1.6212(5) 0.1721(4) 1.0268(4) 0.0361(15) Uani 1 1 d . . . H46A H 1.6753 0.1353 1.0269 0.043 Uiso 1 1 calc R . . H46B H 1.6171 0.1941 1.0694 0.043 Uiso 1 1 calc R . . C42 C 1.6951(4) -0.1376(4) 0.7962(4) 0.0357(12) Uani 1 1 d . . . C47 C 1.4534(5) 0.1594(5) 1.0094(4) 0.0267(15) Uani 1 1 d . . . H47A H 1.4555 0.1981 1.0467 0.032 Uiso 1 1 calc R . . H47B H 1.4432 0.1994 0.9729 0.032 Uiso 1 1 calc R . . C35 C 1.7700(4) 0.1669(5) 0.8589(4) 0.0370(13) Uani 1 1 d . . . H35A H 1.7360 0.1928 0.8221 0.044 Uiso 1 1 calc R . . H35B H 1.8330 0.1777 0.8548 0.044 Uiso 1 1 calc R . . C50 C 1.2579(4) 0.0266(3) 1.0663(3) 0.044(2) Uani 1 1 d . . . H50 H 1.2279 0.0231 1.1024 0.053 Uiso 1 1 calc R . . C3 C 2.0228(4) 0.3903(4) 0.4509(5) 0.034(2) Uani 1 1 d . . . H3C H 2.0373 0.3460 0.4845 0.049 Uiso 1 1 calc R . . H3D H 2.0166 0.3563 0.4115 0.049 Uiso 1 1 calc R . . C7 C 2.2487(5) 0.5668(5) 0.4454(5) 0.034(2) Uani 1 1 d . . . H7A H 2.2998 0.6029 0.4445 0.047 Uiso 1 1 calc R . . C36 C 1.7814(4) 0.0136(5) 0.8043(5) 0.039(2) Uani 1 1 d . . . H36A H 1.7435 0.0323 0.7671 0.055 Uiso 1 1 calc R . . H36B H 1.8426 0.0297 0.7977 0.055 Uiso 1 1 calc R . . O37 O 1.0038(5) 0.9144(4) 0.7331(4) 0.037(3) Uani 1 1 d . . . C15 C 1.7620(3) 0.7588(4) 0.6349(4) 0.038(2) Uani 1 1 d . . . H15 H 1.8151 0.7920 0.6355 0.045 Uiso 1 1 calc R . . O36 O 1.1044(5) 0.7971(5) 0.6874(4) 0.048(3) Uani 1 1 d . . . C10 C 2.1157(3) 0.5514(4) 0.6075(4) 0.0362(12) Uani 1 1 d . . . H10C H 2.1173 0.6149 0.5928 0.043 Uiso 1 1 calc R . . H10D H 2.1750 0.5350 0.6263 0.043 Uiso 1 1 calc R . . C24 C 2.1502(5) 0.5211(5) 0.7951(4) 0.034(2) Uani 1 1 d . . . H24A H 2.2022 0.5266 0.8256 0.049 Uiso 1 1 calc R . . H24B H 2.0971 0.5254 0.8175 0.049 Uiso 1 1 calc R . . C45 C 1.6281(3) 0.2551(4) 0.9833(3) 0.0357(13) Uani 1 1 d . . . H45A H 1.5722 0.2891 0.9805 0.043 Uiso 1 1 calc R . . H45B H 1.6750 0.2960 1.0014 0.043 Uiso 1 1 calc R . . C31 C 2.1366(3) 0.2644(5) 0.7005(5) 0.035(2) Uani 1 1 d . . . H31A H 2.1600 0.2080 0.6836 0.054 Uiso 1 1 calc R . . H31B H 2.1603 0.3167 0.6789 0.054 Uiso 1 1 calc R . . O38 O 1.1030(3) 0.9865(3) 0.6734(3) 0.047(5) Uani 1 1 d . . . C5 C 2.1366(3) 0.4693(4) 0.3944(4) 0.038(2) Uani 1 1 d . . . H5 H 2.1113 0.4404 0.3580 0.046 Uiso 1 1 calc R . . C41 C 1.6906(4) -0.2305(5) 0.8010(4) 0.038(2) Uani 1 1 d . . . H41 H 1.6371 -0.2613 0.7892 0.046 Uiso 1 1 calc R . . C25 C 2.1668(4) 0.3567(5) 0.8018(5) 0.035(2) Uani 1 1 d . . . C54 C 1.3678(5) -0.0066(5) 0.8524(4) 0.0345(13) Uani 1 1 d . . . H54A H 1.3069 0.0078 0.8361 0.041 Uiso 1 1 calc R . . H54B H 1.3709 -0.0714 0.8642 0.041 Uiso 1 1 calc R . . C65 C 1.3448(5) 0.0793(4) 0.6642(4) 0.0357(12) Uani 1 1 d . . . H65A H 1.3968 0.0681 0.6416 0.043 Uiso 1 1 calc R . . H65B H 1.2936 0.0887 0.6336 0.043 Uiso 1 1 calc R . . C16 C 1.6848(5) 0.7939(4) 0.6046(4) 0.042(2) Uani 1 1 d . . . H16 H 1.6858 0.8518 0.5855 0.051 Uiso 1 1 calc R . . C17 C 1.6073(3) 0.7459(3) 0.6019(4) 0.0369(12) Uani 1 1 d . . . H17 H 1.5558 0.7692 0.5798 0.044 Uiso 1 1 calc R . . C61 C 1.3459(5) 0.4195(5) 0.6157(4) 0.0359(15) Uani 1 1 d . . . H61 H 1.3437 0.4779 0.5972 0.043 Uiso 1 1 calc R . . O21 O 1.9207(5) 0.4632(5) 0.8485(4) 0.045(3) Uani 1 1 d . . . C18 C 1.6057(4) 0.6614(5) 0.6326(4) 0.0376(15) Uani 1 1 d . . . H18 H 1.5522 0.6289 0.6323 0.045 Uiso 1 1 calc R . . C1 C 1.8625(3) 0.2968(3) 0.5053(4) 0.0370(13) Uani 1 1 d . . . H1A H 1.8135 0.2534 0.4973 0.044 Uiso 1 1 calc R . . H1B H 1.9182 0.2633 0.5040 0.044 Uiso 1 1 calc R . . C2 C 1.8554(4) 0.3728(5) 0.4550(4) 0.039(2) Uani 1 1 d . . . H2A H 1.8491 0.3444 0.4136 0.047 Uiso 1 1 calc R . . H2B H 1.8024 0.4097 0.4593 0.047 Uiso 1 1 calc R . . C14 C 1.7607(4) 0.6746(3) 0.6643(4) 0.0373(14) Uani 1 1 d . . . C44 C 1.4837(3) -0.0640(3) 0.7090(4) 0.0328(14) Uani 1 1 d . . . H44A H 1.4620 -0.0886 0.6681 0.039 Uiso 1 1 calc R . . H44B H 1.5159 -0.0072 0.7024 0.039 Uiso 1 1 calc R . . C6 C 2.2120(4) 0.5240(3) 0.3906(3) 0.037(2) Uani 1 1 d . . . H6 H 2.2371 0.5317 0.3527 0.056 Uiso 1 1 calc R . . C43 C 1.5463(5) -0.1324(5) 0.7425(4) 0.0317(15) Uani 1 1 d . . . H43A H 1.5161 -0.1654 0.7739 0.038 Uiso 1 1 calc R . . H43B H 1.5655 -0.1772 0.7127 0.038 Uiso 1 1 calc R . . OW6 O 1.3185(5) 0.7973(4) 0.7769(4) 0.045(4) Uani 1 1 d . . . C38 C 1.8491(4) -0.1357(4) 0.8347(5) 0.043(2) Uani 1 1 d . . . H38 H 1.9025 -0.1044 0.8459 0.058 Uiso 1 1 calc R . . C12 C 1.9872(3) 0.6341(3) 0.7402(4) 0.034(2) Uani 1 1 d . . . H12A H 2.0054 0.6687 0.7782 0.053 Uiso 1 1 calc R . . H12B H 1.9624 0.5756 0.7524 0.053 Uiso 1 1 calc R . . C27 C 2.2090(5) 0.2742(5) 0.8986(4) 0.033(4) Uani 1 1 d . . . H27 H 2.2223 0.2749 0.9421 0.079 Uiso 1 1 calc R . . C39 C 1.8461(3) -0.2331(3) 0.8419(3) 0.037(3) Uani 1 1 d . . . H39 H 1.8967 -0.2651 0.8586 0.064 Uiso 1 1 calc R . . C33 C 1.8975(5) 0.2732(5) 0.6177(5) 0.0350(12) Uani 1 1 d . . . H33A H 1.8787 0.2105 0.6068 0.042 Uiso 1 1 calc R . . H33B H 1.8751 0.2889 0.6575 0.042 Uiso 1 1 calc R . . C30 C 2.1638(5) 0.2709(5) 0.7707(5) 0.035(2) Uani 1 1 d . . . C34 C 1.7440(4) 0.2162(5) 0.9174(4) 0.0367(13) Uani 1 1 d . . . H34A H 1.7672 0.1813 0.9543 0.044 Uiso 1 1 calc R . . H34B H 1.7721 0.2767 0.9199 0.044 Uiso 1 1 calc R . . OW3 O 1.8069(4) -0.0160(5) 0.9752(5) 0.047(4) Uani 1 1 d . . . C28 C 2.2068(5) 0.1957(4) 0.8694(4) 0.038(4) Uani 1 1 d . . . H28 H 2.2208 0.1418 0.8921 0.082 Uiso 1 1 calc R . . C29 C 2.1841(5) 0.1900(4) 0.8051(5) 0.036(3) Uani 1 1 d . . . H29 H 2.1824 0.1328 0.7850 0.063 Uiso 1 1 calc R . . C40 C 1.7676(4) -0.2807(5) 0.8240(4) 0.045(3) Uani 1 1 d . . . H40 H 1.7657 -0.3449 0.8271 0.073 Uiso 1 1 calc R . . O31 O 1.0786(5) 0.7712(5) 0.8471(4) 0.045(4) Uani 1 1 d . . . O32 O 1.1186(4) 0.7991(3) 0.9524(3) 0.052(5) Uani 1 1 d . . . C26 C 2.1915(5) 0.3614(5) 0.8658(5) 0.033(3) Uani 1 1 d . . . H26 H 2.1966 0.4178 0.8869 0.071 Uiso 1 1 calc R . . O34 O 1.2279(4) 0.7702(4) 0.8849(4) 0.045(4) Uani 1 1 d . . . O35 O 1.1478(3) 0.937(3) 0.7729(3) 0.05(3) Uani 1 1 d . . . OW4 O 1.9749(5) -0.074(4) 1.0277(5) 0.050(5) Uani 1 1 d . . . OW5 O 1.9979(4) 0.141(3) 0.926(3) 0.045(4) Uani 1 1 d . . . O33 O 1.1311(5) 0.6581(5) 0.9110(4) 0.045(6) Uani 1 1 d . . . OW1 O 1.4413(5) 0.9538(5) 0.4498(4) 0.059(2) Uani 1 1 d . . . OW7 O 0.9774(4) 1.0959(5) 0.7410(5) 0.044(4) Uani 1 1 d . . . OW8 O 2.0535(3) -0.035(4) 0.8899(3) 0.049(5) 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 Cl6 0.0285(9) 0.0305(9) 0.0298(10) -0.0031(8) 0.0030(7) -0.0019(7) Cl5 0.0352(10) 0.0269(8) 0.0271(9) -0.0021(7) 0.0039(7) -0.0036(7) Cl1 0.0425(11) 0.0328(9) 0.0298(10) -0.0030(8) 0.0117(8) -0.0061(8) Cl3 0.0445(12) 0.0362(11) 0.0356(11) -0.0031(9) 0.0008(9) -0.0016(9) Cl2 0.0537(13) 0.0258(9) 0.0299(10) 0.0002(8) 0.0053(9) 0.0008(8) Cl4 0.0457(13) 0.0508(13) 0.0449(13) 0.0006(11) 0.0167(10) -0.0055(10) Cl7 0.067(3) 0.041(3) 0.030(3) -0.006(2) -0.010(2) 0.002(2) Cl8 0.054(3) 0.033(3) 0.032(2) 0.005(2) 0.009(2) -0.003(2) O5 0.037(3) 0.027(3) 0.021(3) 0.000(2) 0.000(2) -0.001(2) O4 0.049(4) 0.029(3) 0.027(3) -0.002(2) 0.000(3) -0.003(2) O10 0.057(4) 0.029(3) 0.034(3) -0.003(2) 0.016(3) -0.006(3) O20 0.045(4) 0.043(4) 0.032(3) 0.000(3) 0.007(3) 0.000(3) O30 0.031(3) 0.053(4) 0.028(3) -0.005(3) -0.006(2) -0.002(3) O25 0.045(4) 0.034(3) 0.025(3) -0.005(3) 0.009(3) -0.007(3) O2 0.035(3) 0.053(4) 0.036(3) -0.001(3) -0.006(3) 0.009(3) O12 0.057(4) 0.040(3) 0.035(3) -0.001(3) 0.009(3) -0.003(3) O1 0.028(3) 0.041(3) 0.031(3) -0.001(2) 0.006(2) -0.008(2) O13 0.059(5) 0.034(3) 0.027(3) -0.004(3) 0.011(3) -0.003(3) O28 0.034(3) 0.032(3) 0.054(4) -0.002(3) 0.002(3) -0.003(2) O27 0.041(3) 0.035(3) 0.038(3) -0.008(3) 0.010(3) -0.002(2) O24 0.040(3) 0.028(3) 0.036(3) -0.009(2) 0.014(3) 0.000(2) O7 0.065(4) 0.030(3) 0.028(3) -0.002(2) 0.014(3) -0.007(3) O16 0.058(4) 0.056(4) 0.042(4) -0.001(3) 0.007(3) -0.002(3) O14 0.050(4) 0.029(3) 0.044(4) 0.001(3) 0.011(3) -0.002(3) O26 0.049(4) 0.030(3) 0.035(3) -0.007(3) 0.004(3) -0.004(3) O9 0.061(4) 0.041(4) 0.043(4) 0.003(3) 0.001(3) 0.003(3) N8 0.035(4) 0.026(3) 0.029(4) 0.002(3) 0.000(3) 0.003(3) O6 0.051(4) 0.028(3) 0.034(3) 0.000(2) 0.001(3) -0.002(3) N7 0.042(4) 0.026(3) 0.030(4) -0.003(3) 0.002(3) -0.003(3) O11 0.046(4) 0.043(4) 0.052(4) 0.000(3) 0.012(3) 0.004(3) O18 0.046(4) 0.033(3) 0.028(5) -0.002(3) -0.003(4) 0.005(3) O8 0.069(5) 0.029(3) 0.039(4) 0.001(3) -0.006(3) -0.002(3) O29 0.027(3) 0.056(4) 0.050(4) -0.003(3) 0.012(3) -0.008(3) O3 0.023(3) 0.039(3) 0.050(4) -0.001(3) 0.000(2) -0.003(2) O23 0.025(3) 0.047(4) 0.042(3) -0.003(3) -0.001(2) 0.001(2) N6 0.043(4) 0.037(4) 0.014(3) -0.003(3) 0.001(3) -0.004(3) O17 0.039(4) 0.041(5) 0.030(5) -0.010(4) 0.002(3) 0.005(3) N1 0.033(4) 0.034(4) 0.028(4) -0.002(3) 0.000(3) 0.003(3) N2 0.032(4) 0.057(5) 0.026(4) -0.004(3) -0.005(3) -0.002(3) C48 0.028(4) 0.027(4) 0.026(4) 0.007(3) 0.004(3) -0.002(3) OW2 0.052(4) 0.061(5) 0.038(4) -0.003(3) 0.011(3) 0.004(3) N5 0.025(3) 0.039(4) 0.038(4) 0.000(3) 0.005(3) -0.003(3) N3 0.033(4) 0.046(4) 0.025(3) -0.007(3) -0.006(3) 0.001(3) C9 0.026(4) 0.024(4) 0.035(4) 0.002(3) -0.001(3) -0.003(3) C59 0.029(4) 0.035(4) 0.029(4) 0.005(3) -0.004(3) -0.001(3) C32 0.028(4) 0.051(5) 0.030(4) -0.004(4) -0.005(3) 0.002(4) N10 0.041(4) 0.033(4) 0.042(4) 0.001(3) 0.000(3) -0.001(3) C37 0.043(5) 0.044(5) 0.039(5) -0.008(4) 0.002(4) 0.004(4) O15 0.053(4) 0.069(5) 0.045(4) 0.007(4) -0.008(3) -0.002(4) C63 0.038(4) 0.041(5) 0.021(4) -0.004(3) -0.003(3) -0.002(4) N9 0.030(3) 0.030(3) 0.025(3) 0.002(3) 0.000(3) -0.003(3) C19 0.035(4) 0.030(4) 0.029(4) -0.008(3) 0.014(3) -0.001(3) C58 0.038(4) 0.030(4) 0.026(4) -0.004(3) 0.004(3) -0.002(3) C66 0.040(5) 0.031(4) 0.036(5) 0.003(3) 0.006(4) -0.003(3) O22 0.031(4) 0.047(7) 0.021(7) 0.018(6) 0.007(4) 0.001(4) C52 0.039(5) 0.030(4) 0.031(4) 0.003(3) -0.004(3) -0.005(3) C53 0.030(4) 0.024(4) 0.033(4) -0.001(3) 0.004(3) 0.002(3) C57 0.040(4) 0.032(4) 0.020(4) -0.001(3) 0.004(3) -0.002(3) C11 0.033(5) 0.040(5) 0.042(5) -0.001(4) -0.005(4) -0.005(4) C13 0.038(5) 0.041(5) 0.043(5) -0.002(4) -0.005(4) -0.006(4) O19 0.056(5) 0.041(5) 0.038(5) 0.012(4) 0.006(4) -0.003(4) C62 0.038(5) 0.045(5) 0.028(4) 0.000(4) -0.004(4) 0.002(4) C60 0.043(5) 0.035(4) 0.029(4) -0.008(3) 0.001(4) -0.004(4) N4 0.027(4) 0.033(4) 0.052(5) -0.001(3) -0.013(3) -0.003(3) C56 0.046(5) 0.033(4) 0.020(4) -0.005(3) 0.002(3) -0.005(4) C4 0.030(4) 0.035(4) 0.041(5) 0.002(4) -0.014(4) 0.002(3) C64 0.034(4) 0.035(4) 0.023(4) 0.010(3) -0.007(3) -0.002(3) C8 0.036(5) 0.039(5) 0.041(5) 0.011(4) -0.008(4) 0.003(4) C55 0.054(5) 0.017(3) 0.026(4) -0.003(3) 0.006(4) -0.004(3) C23 0.043(4) 0.029(5) 0.024(5) -0.004(4) -0.002(3) -0.001(4) C49 0.034(4) 0.040(5) 0.029(4) -0.008(3) 0.008(3) -0.001(4) C21 0.026(4) 0.031(4) 0.035(4) -0.005(3) 0.000(3) -0.001(3) C22 0.033(4) 0.031(4) 0.045(5) -0.005(4) 0.002(4) 0.001(3) C51 0.031(4) 0.029(4) 0.033(6) 0.005(4) 0.007(4) -0.005(3) C20 0.031(4) 0.037(4) 0.037(5) 0.000(4) 0.013(4) -0.005(3) C46 0.030(4) 0.038(5) 0.039(5) 0.008(4) -0.003(4) -0.001(3) C42 0.050(5) 0.033(4) 0.026(4) -0.011(3) 0.011(4) 0.003(4) C47 0.029(4) 0.021(3) 0.029(4) -0.002(3) -0.003(3) -0.003(3) C35 0.036(4) 0.040(5) 0.035(5) -0.005(4) 0.002(4) 0.006(4) C50 0.041(5) 0.047(5) 0.044(5) -0.008(4) 0.002(4) 0.002(4) C3 0.047(4) 0.031(5) 0.022(6) -0.010(4) -0.002(4) 0.001(4) C7 0.043(5) 0.031(4) 0.028(5) 0.003(4) 0.007(4) -0.001(4) C36 0.042(5) 0.042(5) 0.032(6) 0.001(4) -0.002(4) -0.007(4) O37 0.046(6) 0.037(6) 0.027(6) -0.010(5) 0.006(5) -0.003(4) C15 0.034(4) 0.045(5) 0.035(5) -0.007(4) 0.006(4) -0.002(4) O36 0.059(4) 0.047(4) 0.039(4) 0.007(5) 0.004(5) -0.001(5) C10 0.042(4) 0.038(5) 0.029(5) 0.003(4) 0.001(4) -0.002(3) C24 0.044(4) 0.037(6) 0.021(4) 0.007(4) 0.004(3) -0.004(4) C45 0.033(4) 0.047(5) 0.026(4) 0.000(4) -0.008(3) -0.005(4) C31 0.041(5) 0.035(5) 0.029(6) 0.004(4) 0.002(4) 0.001(4) O38 0.062(6) 0.042(6) 0.039(6) -0.013(5) 0.010(5) -0.002(5) C5 0.039(5) 0.041(5) 0.036(5) 0.010(4) 0.005(4) 0.003(4) C41 0.052(5) 0.029(4) 0.035(5) 0.008(3) 0.004(4) 0.002(4) C25 0.047(4) 0.032(7) 0.025(5) 0.007(5) -0.004(4) -0.002(4) C54 0.043(5) 0.030(4) 0.030(4) -0.002(3) 0.003(4) -0.004(3) C65 0.046(5) 0.037(4) 0.025(4) -0.005(3) 0.004(3) -0.004(4) C16 0.047(5) 0.042(5) 0.037(5) -0.005(4) 0.005(4) 0.002(4) C17 0.030(4) 0.049(5) 0.032(4) -0.008(4) 0.007(3) 0.003(4) C61 0.048(5) 0.030(4) 0.028(4) 0.008(3) -0.004(4) -0.003(3) O21 0.059(5) 0.048(5) 0.031(5) -0.002(4) 0.014(4) -0.002(4) C18 0.028(4) 0.044(5) 0.041(5) -0.002(4) 0.002(4) -0.002(3) C1 0.038(5) 0.037(4) 0.035(5) -0.004(4) -0.002(4) -0.002(4) C2 0.038(5) 0.042(5) 0.036(5) -0.001(4) 0.003(4) 0.002(4) C14 0.049(4) 0.033(5) 0.023(5) -0.003(4) 0.005(4) 0.002(3) C44 0.050(5) 0.025(4) 0.024(4) 0.000(3) 0.007(4) 0.000(3) C6 0.049(6) 0.040(5) 0.024(6) 0.009(5) 0.007(5) 0.002(4) C43 0.038(4) 0.026(4) 0.032(4) -0.009(3) 0.007(3) -0.001(3) OW6 0.059(6) 0.044(6) 0.032(6) 0.002(5) 0.012(5) 0.003(5) C38 0.054(6) 0.045(5) 0.030(6) -0.003(5) 0.007(5) 0.003(4) C12 0.040(4) 0.032(6) 0.030(6) -0.007(5) 0.001(4) -0.002(4) C27 0.038(6) 0.037(12) 0.022(6) 0.010(7) -0.003(5) 0.002(6) C39 0.054(6) 0.033(6) 0.025(6) -0.004(5) 0.006(5) 0.003(5) C33 0.031(4) 0.035(4) 0.040(5) -0.006(4) 0.009(4) 0.002(3) C30 0.043(4) 0.032(4) 0.030(4) 0.009(3) -0.003(3) -0.001(3) C34 0.040(5) 0.034(4) 0.035(5) 0.002(3) -0.003(4) -0.004(3) OW3 0.062(4) 0.046(4) 0.031(4) 0.006(5) -0.006(5) 0.003(5) C28 0.054(5) 0.039(5) 0.022(5) 0.006(4) 0.005(4) 0.001(4) C29 0.048(6) 0.038(6) 0.023(6) 0.008(5) 0.006(5) 0.001(5) C40 0.060(6) 0.045(6) 0.031(6) 0.012(5) 0.004(5) 0.001(5) O31 0.054(3) 0.045(3) 0.034(3) -0.004(4) -0.002(4) 0.003(4) O32 0.069(4) 0.050(4) 0.038(4) -0.006(5) 0.011(5) -0.003(5) C26 0.044(5) 0.032(9) 0.023(7) 0.008(6) 0.004(5) 0.003(5) O34 0.054(6) 0.047(6) 0.034(6) 0.015(5) 0.003(5) 0.002(5) O35 0.060(5) 0.054(5) 0.034(5) 0.011(4) -0.007(4) -0.002(4) OW4 0.066(6) 0.048(5) 0.035(5) 0.012(4) 0.006(4) -0.004(4) OW5 0.057(5) 0.047(5) 0.031(5) 0.017(4) 0.009(4) 0.003(3) O33 0.056(4) 0.043(4) 0.036(4) -0.006(3) 0.011(3) -0.003(3) OW1 0.056(5) 0.051(4) 0.064(5) 0.002(4) -0.018(4) 0.000(3) OW7 0.060(4) 0.043(4) 0.032(4) -0.005(3) 0.016(3) -0.004(3) OW8 0.065(2) 0.048(2) 0.034(3) -0.013(8) 0.008(2) -0.002(7) _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 Cl6 O30 1.424(6) . ? Cl6 O29 1.438(6) . ? Cl6 O27 1.441(6) . ? Cl6 O28 1.452(7) . ? Cl5 O26 1.413(6) . ? Cl5 O23 1.428(6) . ? Cl5 O25 1.446(6) . ? Cl5 O24 1.456(6) . ? Cl1 O13 1.439(7) . ? Cl1 O12 1.443(6) . ? Cl1 O14 1.445(7) . ? Cl1 O11 1.446(7) . ? Cl3 O18 1.394(7) . ? Cl3 O17 1.426(7) . ? Cl3 O16 1.437(7) . ? Cl3 O15 1.442(7) . ? Cl2 O7 1.410(6) . ? Cl2 O9 1.413(7) . ? Cl2 O8 1.439(7) . ? Cl2 O10 1.471(6) . ? Cl4 O22 1.413(8) . ? Cl4 O21 1.425(10) . ? Cl4 O19 1.441(9) . ? Cl4 O20 1.465(6) . ? Cl7 O31 1.350(15) . ? Cl7 O33 1.373(16) . ? Cl7 O32 1.409(14) . ? Cl7 O34 1.453(12) . ? Cl8 O37 1.454(9) . ? Cl8 O35 1.471(18) . ? Cl8 O36 1.579(11) . ? Cl8 O38 1.647(7) . ? O5 C53 1.380(10) . ? O5 C54 1.442(10) . ? O4 C64 1.366(10) . ? O4 C65 1.445(10) . ? O2 C25 1.371(12) . ? O2 C24 1.412(12) . ? O1 C9 1.331(10) . ? O1 C10 1.452(11) . ? N8 C57 1.489(10) . ? N8 C58 1.537(11) . ? N8 H8A 0.9000 . ? N8 H8B 0.9000 . ? O6 C42 1.379(11) . ? O6 C43 1.461(10) . ? N7 C34 1.452(11) . ? N7 C56 1.460(11) . ? N7 C45 1.491(11) . ? N7 H7 0.9100 . ? O3 C14 1.388(10) . ? O3 C13 1.431(10) . ? N6 C66 1.497(11) . ? N6 C55 1.500(10) . ? N6 C44 1.510(11) . ? N1 C22 1.449(11) . ? N1 C1 1.464(11) . ? N1 C33 1.503(11) . ? N1 H1 0.9100 . ? N2 C12 1.470(12) . ? N2 C23 1.508(11) . ? N2 C11 1.527(12) . ? C48 C49 1.388(11) . ? C48 C53 1.398(12) . ? C48 C47 1.496(10) . ? N5 C21 1.478(10) . ? N5 C20 1.506(11) . ? N5 H5A 0.9000 . ? N5 H5B 0.9000 . ? N3 C2 1.486(12) . ? N3 C3 1.486(11) . ? N3 H3A 0.9000 . ? N3 H3B 0.9000 . ? C9 C8 1.388(12) . ? C9 C4 1.411(12) . ? C59 C60 1.364(12) . ? C59 C64 1.423(12) . ? C59 C58 1.510(12) . ? C32 N4 1.481(11) . ? C32 C33 1.527(12) . ? C32 H32A 0.9700 . ? C32 H32B 0.9700 . ? N10 C35 1.463(12) . ? N10 C36 1.524(13) . ? N10 H10A 0.9000 . ? N10 H10B 0.9000 . ? C37 C38 1.368(15) . ? C37 C42 1.418(14) . ? C37 C36 1.464(14) . ? C63 C62 1.378(13) . ? C63 C64 1.396(11) . ? C63 H63 0.9300 . ? N9 C46 1.495(11) . ? N9 C47 1.500(10) . ? N9 H9A 0.9000 . ? N9 H9B 0.9000 . ? C19 C14 1.370(12) . ? C19 C18 1.382(12) . ? C19 C20 1.516(12) . ? C58 H58A 0.9700 . ? C58 H58B 0.9700 . ? C66 C65 1.494(12) . ? C66 H66A 0.9700 . ? C66 H66B 0.9700 . ? C52 C53 1.374(12) . ? C52 C51 1.406(13) . ? C52 H52 0.9300 . ? C57 C56 1.527(12) . ? C57 H57A 0.9700 . ? C57 H57B 0.9700 . ? C11 C10 1.507(13) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C13 C12 1.532(14) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C62 C61 1.405(13) . ? C62 H62 0.9300 . ? C60 C61 1.385(12) . ? C60 H60 0.9300 . ? N4 C31 1.520(12) . ? N4 H4A 0.9000 . ? N4 H4B 0.9000 . ? C56 H56A 0.9700 . ? C56 H56B 0.9700 . ? C4 C5 1.381(13) . ? C4 C3 1.468(13) . ? C8 C7 1.400(13) . ? C8 H8 0.9300 . ? C55 C54 1.513(12) . ? C55 H55A 0.9700 . ? C55 H55B 0.9700 . ? C23 C24 1.489(14) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C49 C50 1.418(13) . ? C49 H49 0.9300 . ? C21 C22 1.506(11) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C51 C50 1.366(14) . ? C51 H51 0.9300 . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C46 C45 1.526(12) . ? C46 H46A 0.9700 . ? C46 H46B 0.9700 . ? C42 C41 1.349(12) . ? C47 H47A 0.9700 . ? C47 H47B 0.9700 . ? C35 C34 1.520(12) . ? C35 H35A 0.9700 . ? C35 H35B 0.9700 . ? C50 H50 0.9300 . ? C3 H3C 0.9700 . ? C3 H3D 0.9700 . ? C7 C6 1.388(15) . ? C7 H7A 0.9300 . ? C36 H36A 0.9700 . ? C36 H36B 0.9700 . ? C15 C16 1.368(13) . ? C15 C14 1.370(13) . ? C15 H15 0.9300 . ? C10 H10C 0.9700 . ? C10 H10D 0.9700 . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C45 H45A 0.9700 . ? C45 H45B 0.9700 . ? C31 C30 1.518(14) . ? C31 H31A 0.9700 . ? C31 H31B 0.9700 . ? C5 C6 1.390(14) . ? C5 H5 0.9300 . ? C41 C40 1.412(15) . ? C41 H41 0.9300 . ? C25 C26 1.383(15) . ? C25 C30 1.406(16) . ? C54 H54A 0.9700 . ? C54 H54B 0.9700 . ? C65 H65A 0.9700 . ? C65 H65B 0.9700 . ? C16 C17 1.351(14) . ? C16 H16 0.9300 . ? C17 C18 1.386(13) . ? C17 H17 0.9300 . ? C61 H61 0.9300 . ? C18 H18 0.9300 . ? C1 C2 1.532(13) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C44 C43 1.497(12) . ? C44 H44A 0.9700 . ? C44 H44B 0.9700 . ? C6 H6 0.9300 . ? C43 H43A 0.9700 . ? C43 H43B 0.9700 . ? C38 C39 1.416(7) . ? C38 H38 0.9300 . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C27 C28 1.29(2) . ? C27 C26 1.454(19) . ? C27 H27 0.9300 . ? C39 C40 1.386(8) . ? C39 H39 0.9300 . ? C33 H33A 0.9700 . ? C33 H33B 0.9700 . ? C30 C29 1.398(15) . ? C34 H34A 0.9700 . ? C34 H34B 0.9700 . ? C28 C29 1.384(18) . ? C28 H28 0.9300 . ? C29 H29 0.9300 . ? C40 H40 0.9300 . ? C26 H26 0.9300 . ? 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 O30 Cl6 O29 110.1(4) . . ? O30 Cl6 O27 110.1(4) . . ? O29 Cl6 O27 109.1(4) . . ? O30 Cl6 O28 108.7(4) . . ? O29 Cl6 O28 109.3(4) . . ? O27 Cl6 O28 109.5(4) . . ? O26 Cl5 O23 110.1(4) . . ? O26 Cl5 O25 110.8(4) . . ? O23 Cl5 O25 109.0(4) . . ? O26 Cl5 O24 110.5(4) . . ? O23 Cl5 O24 109.0(4) . . ? O25 Cl5 O24 107.4(4) . . ? O13 Cl1 O12 109.6(4) . . ? O13 Cl1 O14 108.8(4) . . ? O12 Cl1 O14 108.7(4) . . ? O13 Cl1 O11 110.4(4) . . ? O12 Cl1 O11 110.9(4) . . ? O14 Cl1 O11 108.4(4) . . ? O18 Cl3 O17 109.7(5) . . ? O18 Cl3 O16 110.0(5) . . ? O17 Cl3 O16 109.2(5) . . ? O18 Cl3 O15 109.8(5) . . ? O17 Cl3 O15 109.8(5) . . ? O16 Cl3 O15 108.3(4) . . ? O7 Cl2 O9 109.2(4) . . ? O7 Cl2 O8 110.9(4) . . ? O9 Cl2 O8 110.3(4) . . ? O7 Cl2 O10 108.6(4) . . ? O9 Cl2 O10 109.4(4) . . ? O8 Cl2 O10 108.4(4) . . ? O22 Cl4 O21 114.1(7) . . ? O22 Cl4 O19 109.8(5) . . ? O21 Cl4 O19 109.0(7) . . ? O22 Cl4 O20 108.3(5) . . ? O21 Cl4 O20 107.5(5) . . ? O19 Cl4 O20 107.9(5) . . ? O31 Cl7 O33 109.5(5) . . ? O31 Cl7 O32 113.4(10) . . ? O33 Cl7 O32 106.9(5) . . ? O31 Cl7 O34 110.8(5) . . ? O33 Cl7 O34 107.5(5) . . ? O32 Cl7 O34 108.4(8) . . ? O37 Cl8 O35 101.7(13) . . ? O37 Cl8 O36 112.7(6) . . ? O35 Cl8 O36 129.7(16) . . ? O37 Cl8 O38 95.5(7) . . ? O35 Cl8 O38 93.9(10) . . ? O36 Cl8 O38 117.1(6) . . ? C53 O5 C54 115.5(6) . . ? C64 O4 C65 116.0(6) . . ? C25 O2 C24 118.3(7) . . ? C9 O1 C10 115.0(6) . . ? C57 N8 C58 113.2(6) . . ? C57 N8 H8A 108.9 . . ? C58 N8 H8A 108.9 . . ? C57 N8 H8B 108.9 . . ? C58 N8 H8B 108.9 . . ? H8A N8 H8B 107.8 . . ? C42 O6 C43 116.2(6) . . ? C34 N7 C56 111.7(7) . . ? C34 N7 C45 109.6(7) . . ? C56 N7 C45 109.1(7) . . ? C34 N7 H7 108.8 . . ? C56 N7 H7 108.8 . . ? C45 N7 H7 108.8 . . ? C14 O3 C13 115.0(7) . . ? C66 N6 C55 114.1(7) . . ? C66 N6 C44 111.3(6) . . ? C55 N6 C44 111.9(7) . . ? C22 N1 C1 112.7(7) . . ? C22 N1 C33 107.8(7) . . ? C1 N1 C33 110.0(7) . . ? C22 N1 H1 108.7 . . ? C1 N1 H1 108.7 . . ? C33 N1 H1 108.7 . . ? C12 N2 C23 113.5(7) . . ? C12 N2 C11 112.4(7) . . ? C23 N2 C11 112.9(7) . . ? C49 C48 C53 119.4(7) . . ? C49 C48 C47 118.9(7) . . ? C53 C48 C47 121.7(7) . . ? C21 N5 C20 115.7(6) . . ? C21 N5 H5A 108.3 . . ? C20 N5 H5A 108.3 . . ? C21 N5 H5B 108.3 . . ? C20 N5 H5B 108.4 . . ? H5A N5 H5B 107.4 . . ? C2 N3 C3 117.0(7) . . ? C2 N3 H3A 108.1 . . ? C3 N3 H3A 108.1 . . ? C2 N3 H3B 108.1 . . ? C3 N3 H3B 108.0 . . ? H3A N3 H3B 107.3 . . ? O1 C9 C8 125.5(8) . . ? O1 C9 C4 115.3(7) . . ? C8 C9 C4 119.2(8) . . ? C60 C59 C64 119.5(7) . . ? C60 C59 C58 120.9(8) . . ? C64 C59 C58 119.4(7) . . ? N4 C32 C33 110.4(7) . . ? N4 C32 H32A 109.6 . . ? C33 C32 H32A 109.6 . . ? N4 C32 H32B 109.6 . . ? C33 C32 H32B 109.6 . . ? H32A C32 H32B 108.1 . . ? C35 N10 C36 114.7(7) . . ? C35 N10 H10A 108.6 . . ? C36 N10 H10A 108.6 . . ? C35 N10 H10B 108.6 . . ? C36 N10 H10B 108.6 . . ? H10A N10 H10B 107.6 . . ? C38 C37 C42 117.3(9) . . ? C38 C37 C36 119.4(10) . . ? C42 C37 C36 123.3(9) . . ? C62 C63 C64 119.5(8) . . ? C62 C63 H63 120.2 . . ? C64 C63 H63 120.3 . . ? C46 N9 C47 114.3(6) . . ? C46 N9 H9A 108.7 . . ? C47 N9 H9A 108.7 . . ? C46 N9 H9B 108.7 . . ? C47 N9 H9B 108.7 . . ? H9A N9 H9B 107.6 . . ? C14 C19 C18 118.7(8) . . ? C14 C19 C20 122.7(8) . . ? C18 C19 C20 118.6(8) . . ? C59 C58 N8 109.1(6) . . ? C59 C58 H58A 109.9 . . ? N8 C58 H58A 109.9 . . ? C59 C58 H58B 109.9 . . ? N8 C58 H58B 109.9 . . ? H58A C58 H58B 108.3 . . ? C65 C66 N6 119.2(7) . . ? C65 C66 H66A 107.5 . . ? N6 C66 H66A 107.5 . . ? C65 C66 H66B 107.5 . . ? N6 C66 H66B 107.5 . . ? H66A C66 H66B 107.0 . . ? C53 C52 C51 121.3(8) . . ? C53 C52 H52 119.3 . . ? C51 C52 H52 119.3 . . ? C52 C53 O5 125.1(8) . . ? C52 C53 C48 119.4(8) . . ? O5 C53 C48 115.5(7) . . ? N8 C57 C56 110.5(6) . . ? N8 C57 H57A 109.5 . . ? C56 C57 H57A 109.6 . . ? N8 C57 H57B 109.5 . . ? C56 C57 H57B 109.5 . . ? H57A C57 H57B 108.1 . . ? C10 C11 N2 109.9(7) . . ? C10 C11 H11A 109.7 . . ? N2 C11 H11A 109.7 . . ? C10 C11 H11B 109.7 . . ? N2 C11 H11B 109.7 . . ? H11A C11 H11B 108.2 . . ? O3 C13 C12 106.9(8) . . ? O3 C13 H13A 110.3 . . ? C12 C13 H13A 110.3 . . ? O3 C13 H13B 110.3 . . ? C12 C13 H13B 110.3 . . ? H13A C13 H13B 108.6 . . ? C63 C62 C61 121.3(8) . . ? C63 C62 H62 119.4 . . ? C61 C62 H62 119.4 . . ? C59 C60 C61 121.8(8) . . ? C59 C60 H60 119.1 . . ? C61 C60 H60 119.1 . . ? C32 N4 C31 112.9(7) . . ? C32 N4 H4A 109.0 . . ? C31 N4 H4A 109.0 . . ? C32 N4 H4B 109.0 . . ? C31 N4 H4B 109.0 . . ? H4A N4 H4B 107.8 . . ? N7 C56 C57 110.9(7) . . ? N7 C56 H56A 109.5 . . ? C57 C56 H56A 109.5 . . ? N7 C56 H56B 109.5 . . ? C57 C56 H56B 109.5 . . ? H56A C56 H56B 108.0 . . ? C5 C4 C9 118.6(8) . . ? C5 C4 C3 119.6(8) . . ? C9 C4 C3 121.7(8) . . ? O4 C64 C63 124.5(8) . . ? O4 C64 C59 116.0(7) . . ? C63 C64 C59 119.5(7) . . ? C9 C8 C7 120.6(9) . . ? C9 C8 H8 119.7 . . ? C7 C8 H8 119.7 . . ? N6 C55 C54 108.9(7) . . ? N6 C55 H55A 109.9 . . ? C54 C55 H55A 109.9 . . ? N6 C55 H55B 109.9 . . ? C54 C55 H55B 109.9 . . ? H55A C55 H55B 108.3 . . ? C24 C23 N2 118.2(8) . . ? C24 C23 H23A 107.8 . . ? N2 C23 H23A 107.8 . . ? C24 C23 H23B 107.8 . . ? N2 C23 H23B 107.8 . . ? H23A C23 H23B 107.1 . . ? C48 C49 C50 120.9(8) . . ? C48 C49 H49 119.6 . . ? C50 C49 H49 119.6 . . ? N5 C21 C22 111.0(7) . . ? N5 C21 H21A 109.4 . . ? C22 C21 H21A 109.4 . . ? N5 C21 H21B 109.4 . . ? C22 C21 H21B 109.4 . . ? H21A C21 H21B 108.0 . . ? N1 C22 C21 110.1(7) . . ? N1 C22 H22A 109.6 . . ? C21 C22 H22A 109.6 . . ? N1 C22 H22B 109.6 . . ? C21 C22 H22B 109.6 . . ? H22A C22 H22B 108.2 . . ? C50 C51 C52 119.9(8) . . ? C50 C51 H51 120.0 . . ? C52 C51 H51 120.0 . . ? N5 C20 C19 111.3(7) . . ? N5 C20 H20A 109.4 . . ? C19 C20 H20A 109.4 . . ? N5 C20 H20B 109.4 . . ? C19 C20 H20B 109.4 . . ? H20A C20 H20B 108.0 . . ? N9 C46 C45 112.8(7) . . ? N9 C46 H46A 109.0 . . ? C45 C46 H46A 109.0 . . ? N9 C46 H46B 109.0 . . ? C45 C46 H46B 109.0 . . ? H46A C46 H46B 107.8 . . ? C41 C42 O6 123.4(9) . . ? C41 C42 C37 122.9(9) . . ? O6 C42 C37 113.5(8) . . ? C48 C47 N9 113.2(6) . . ? C48 C47 H47A 108.9 . . ? N9 C47 H47A 108.9 . . ? C48 C47 H47B 108.9 . . ? N9 C47 H47B 108.9 . . ? H47A C47 H47B 107.8 . . ? N10 C35 C34 112.4(8) . . ? N10 C35 H35A 109.1 . . ? C34 C35 H35A 109.1 . . ? N10 C35 H35B 109.1 . . ? C34 C35 H35B 109.1 . . ? H35A C35 H35B 107.9 . . ? C51 C50 C49 119.0(9) . . ? C51 C50 H50 120.5 . . ? C49 C50 H50 120.5 . . ? C4 C3 N3 114.3(8) . . ? C4 C3 H3C 108.7 . . ? N3 C3 H3C 108.7 . . ? C4 C3 H3D 108.7 . . ? N3 C3 H3D 108.7 . . ? H3C C3 H3D 107.6 . . ? C6 C7 C8 120.8(9) . . ? C6 C7 H7A 119.6 . . ? C8 C7 H7A 119.6 . . ? C37 C36 N10 113.0(8) . . ? C37 C36 H36A 109.0 . . ? N10 C36 H36A 109.0 . . ? C37 C36 H36B 109.0 . . ? N10 C36 H36B 109.0 . . ? H36A C36 H36B 107.8 . . ? C16 C15 C14 119.8(9) . . ? C16 C15 H15 120.1 . . ? C14 C15 H15 120.1 . . ? O1 C10 C11 108.6(6) . . ? O1 C10 H10C 110.0 . . ? C11 C10 H10C 110.0 . . ? O1 C10 H10D 110.0 . . ? C11 C10 H10D 110.0 . . ? H10C C10 H10D 108.4 . . ? O2 C24 C23 111.7(7) . . ? O2 C24 H24A 109.3 . . ? C23 C24 H24A 109.3 . . ? O2 C24 H24B 109.3 . . ? C23 C24 H24B 109.3 . . ? H24A C24 H24B 107.9 . . ? N7 C45 C46 112.6(8) . . ? N7 C45 H45A 109.1 . . ? C46 C45 H45A 109.1 . . ? N7 C45 H45B 109.1 . . ? C46 C45 H45B 109.1 . . ? H45A C45 H45B 107.8 . . ? C30 C31 N4 107.6(8) . . ? C30 C31 H31A 110.2 . . ? N4 C31 H31A 110.2 . . ? C30 C31 H31B 110.2 . . ? N4 C31 H31B 110.2 . . ? H31A C31 H31B 108.5 . . ? C4 C5 C6 123.1(9) . . ? C4 C5 H5 118.4 . . ? C6 C5 H5 118.4 . . ? C42 C41 C40 119.5(10) . . ? C42 C41 H41 120.3 . . ? C40 C41 H41 120.3 . . ? O2 C25 C26 122.6(11) . . ? O2 C25 C30 116.9(8) . . ? C26 C25 C30 120.2(10) . . ? O5 C54 C55 106.4(6) . . ? O5 C54 H54A 110.5 . . ? C55 C54 H54A 110.5 . . ? O5 C54 H54B 110.5 . . ? C55 C54 H54B 110.5 . . ? H54A C54 H54B 108.6 . . ? O4 C65 C66 110.9(7) . . ? O4 C65 H65A 109.5 . . ? C66 C65 H65A 109.5 . . ? O4 C65 H65B 109.5 . . ? C66 C65 H65B 109.5 . . ? H65A C65 H65B 108.0 . . ? C17 C16 C15 121.1(10) . . ? C17 C16 H16 119.5 . . ? C15 C16 H16 119.5 . . ? C16 C17 C18 119.1(9) . . ? C16 C17 H17 120.5 . . ? C18 C17 H17 120.5 . . ? C60 C61 C62 118.5(8) . . ? C60 C61 H61 120.8 . . ? C62 C61 H61 120.8 . . ? C19 C18 C17 120.7(8) . . ? C19 C18 H18 119.7 . . ? C17 C18 H18 119.7 . . ? N1 C1 C2 109.5(7) . . ? N1 C1 H1A 109.8 . . ? C2 C1 H1A 109.8 . . ? N1 C1 H1B 109.8 . . ? C2 C1 H1B 109.8 . . ? H1A C1 H1B 108.2 . . ? N3 C2 C1 111.8(7) . . ? N3 C2 H2A 109.3 . . ? C1 C2 H2A 109.3 . . ? N3 C2 H2B 109.3 . . ? C1 C2 H2B 109.3 . . ? H2A C2 H2B 107.9 . . ? C19 C14 C15 120.6(8) . . ? C19 C14 O3 115.6(8) . . ? C15 C14 O3 123.7(8) . . ? C43 C44 N6 111.9(7) . . ? C43 C44 H44A 109.2 . . ? N6 C44 H44A 109.2 . . ? C43 C44 H44B 109.2 . . ? N6 C44 H44B 109.2 . . ? H44A C44 H44B 107.9 . . ? C7 C6 C5 117.6(9) . . ? C7 C6 H6 121.2 . . ? C5 C6 H6 121.2 . . ? O6 C43 C44 109.1(7) . . ? O6 C43 H43A 109.9 . . ? C44 C43 H43A 109.9 . . ? O6 C43 H43B 109.8 . . ? C44 C43 H43B 109.9 . . ? H43A C43 H43B 108.3 . . ? C37 C38 C39 121.2(5) . . ? C37 C38 H38 119.4 . . ? C39 C38 H38 119.4 . . ? N2 C12 C13 112.1(8) . . ? N2 C12 H12A 109.2 . . ? C13 C12 H12A 109.2 . . ? N2 C12 H12B 109.2 . . ? C13 C12 H12B 109.2 . . ? H12A C12 H12B 107.9 . . ? C28 C27 C26 122.2(11) . . ? C28 C27 H27 118.9 . . ? C26 C27 H27 118.9 . . ? C40 C39 C38 119.9(5) . . ? C40 C39 H39 120.1 . . ? C38 C39 H39 120.0 . . ? N1 C33 C32 110.5(7) . . ? N1 C33 H33A 109.5 . . ? C32 C33 H33A 109.6 . . ? N1 C33 H33B 109.5 . . ? C32 C33 H33B 109.5 . . ? H33A C33 H33B 108.1 . . ? C29 C30 C25 119.6(9) . . ? C29 C30 C31 119.5(10) . . ? C25 C30 C31 120.9(9) . . ? N7 C34 C35 113.7(7) . . ? N7 C34 H34A 108.8 . . ? C35 C34 H34A 108.8 . . ? N7 C34 H34B 108.8 . . ? C35 C34 H34B 108.8 . . ? H34A C34 H34B 107.7 . . ? C27 C28 C29 121.5(12) . . ? C27 C28 H28 119.2 . . ? C29 C28 H28 119.2 . . ? C28 C29 C30 119.5(12) . . ? C28 C29 H29 120.3 . . ? C30 C29 H29 120.3 . . ? C39 C40 C41 119.1(11) . . ? C39 C40 H40 120.4 . . ? C41 C40 H40 120.4 . . ? C25 C26 C27 116.9(12) . . ? C25 C26 H26 121.5 . . ? C27 C26 H26 121.5 . . ? 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 C10 O1 C9 C8 11.3(12) . . . . ? C10 O1 C9 C4 -168.6(7) . . . . ? C60 C59 C58 N8 -79.9(10) . . . . ? C64 C59 C58 N8 94.1(8) . . . . ? C57 N8 C58 C59 -160.7(7) . . . . ? C55 N6 C66 C65 74.7(9) . . . . ? C44 N6 C66 C65 -53.1(10) . . . . ? C51 C52 C53 O5 -178.5(7) . . . . ? C51 C52 C53 C48 1.5(12) . . . . ? C54 O5 C53 C52 -2.0(11) . . . . ? C54 O5 C53 C48 178.0(7) . . . . ? C49 C48 C53 C52 -0.5(12) . . . . ? C47 C48 C53 C52 -179.5(7) . . . . ? C49 C48 C53 O5 179.5(7) . . . . ? C47 C48 C53 O5 0.5(11) . . . . ? C58 N8 C57 C56 178.8(6) . . . . ? C12 N2 C11 C10 158.8(8) . . . . ? C23 N2 C11 C10 -71.2(9) . . . . ? C14 O3 C13 C12 174.6(7) . . . . ? C64 C63 C62 C61 0.5(13) . . . . ? C64 C59 C60 C61 0.7(13) . . . . ? C58 C59 C60 C61 174.6(8) . . . . ? C33 C32 N4 C31 177.5(7) . . . . ? C34 N7 C56 C57 161.4(7) . . . . ? C45 N7 C56 C57 -77.2(8) . . . . ? N8 C57 C56 N7 -154.1(7) . . . . ? O1 C9 C4 C5 176.6(7) . . . . ? C8 C9 C4 C5 -3.4(12) . . . . ? O1 C9 C4 C3 -6.7(12) . . . . ? C8 C9 C4 C3 173.4(8) . . . . ? C65 O4 C64 C63 -4.4(11) . . . . ? C65 O4 C64 C59 174.1(7) . . . . ? C62 C63 C64 O4 179.2(8) . . . . ? C62 C63 C64 C59 0.7(12) . . . . ? C60 C59 C64 O4 -179.9(8) . . . . ? C58 C59 C64 O4 6.0(11) . . . . ? C60 C59 C64 C63 -1.3(12) . . . . ? C58 C59 C64 C63 -175.3(8) . . . . ? O1 C9 C8 C7 -177.7(8) . . . . ? C4 C9 C8 C7 2.2(13) . . . . ? C66 N6 C55 C54 80.2(8) . . . . ? C44 N6 C55 C54 -152.3(7) . . . . ? C12 N2 C23 C24 57.6(11) . . . . ? C11 N2 C23 C24 -71.8(10) . . . . ? C53 C48 C49 C50 -0.7(13) . . . . ? C47 C48 C49 C50 178.3(8) . . . . ? C20 N5 C21 C22 -179.5(7) . . . . ? C1 N1 C22 C21 -151.4(8) . . . . ? C33 N1 C22 C21 87.0(8) . . . . ? N5 C21 C22 N1 -165.9(7) . . . . ? C53 C52 C51 C50 -1.2(13) . . . . ? C21 N5 C20 C19 66.1(9) . . . . ? C14 C19 C20 N5 -97.4(9) . . . . ? C18 C19 C20 N5 83.9(9) . . . . ? C47 N9 C46 C45 -62.3(9) . . . . ? C43 O6 C42 C41 -10.3(11) . . . . ? C43 O6 C42 C37 166.4(7) . . . . ? C38 C37 C42 C41 -2.5(14) . . . . ? C36 C37 C42 C41 177.5(9) . . . . ? C38 C37 C42 O6 -179.3(8) . . . . ? C36 C37 C42 O6 0.7(13) . . . . ? C49 C48 C47 N9 111.6(8) . . . . ? C53 C48 C47 N9 -69.5(9) . . . . ? C46 N9 C47 C48 -162.0(7) . . . . ? C36 N10 C35 C34 -178.2(7) . . . . ? C52 C51 C50 C49 0.0(14) . . . . ? C48 C49 C50 C51 0.9(14) . . . . ? C5 C4 C3 N3 -112.7(9) . . . . ? C9 C4 C3 N3 70.6(11) . . . . ? C2 N3 C3 C4 173.5(8) . . . . ? C9 C8 C7 C6 0.1(14) . . . . ? C38 C37 C36 N10 -94.1(11) . . . . ? C42 C37 C36 N10 85.9(11) . . . . ? C35 N10 C36 C37 172.5(8) . . . . ? C9 O1 C10 C11 169.1(7) . . . . ? N2 C11 C10 O1 -171.3(7) . . . . ? C25 O2 C24 C23 169.3(7) . . . . ? N2 C23 C24 O2 72.2(10) . . . . ? C34 N7 C45 C46 -84.6(8) . . . . ? C56 N7 C45 C46 152.8(7) . . . . ? N9 C46 C45 N7 -67.1(9) . . . . ? C32 N4 C31 C30 167.8(8) . . . . ? C9 C4 C5 C6 2.4(13) . . . . ? C3 C4 C5 C6 -174.4(9) . . . . ? O6 C42 C41 C40 178.2(9) . . . . ? C37 C42 C41 C40 1.7(14) . . . . ? C24 O2 C25 C26 -8.3(13) . . . . ? C24 O2 C25 C30 177.1(8) . . . . ? C53 O5 C54 C55 -176.8(6) . . . . ? N6 C55 C54 O5 -178.6(6) . . . . ? C64 O4 C65 C66 -165.8(7) . . . . ? N6 C66 C65 O4 -71.6(10) . . . . ? C14 C15 C16 C17 -1.5(14) . . . . ? C15 C16 C17 C18 2.6(14) . . . . ? C59 C60 C61 C62 0.5(14) . . . . ? C63 C62 C61 C60 -1.1(14) . . . . ? C14 C19 C18 C17 0.9(13) . . . . ? C20 C19 C18 C17 179.6(8) . . . . ? C16 C17 C18 C19 -2.3(13) . . . . ? C22 N1 C1 C2 79.5(9) . . . . ? C33 N1 C1 C2 -160.1(7) . . . . ? C3 N3 C2 C1 62.7(10) . . . . ? N1 C1 C2 N3 67.0(9) . . . . ? C18 C19 C14 C15 0.3(13) . . . . ? C20 C19 C14 C15 -178.4(8) . . . . ? C18 C19 C14 O3 -178.0(7) . . . . ? C20 C19 C14 O3 3.3(12) . . . . ? C16 C15 C14 C19 0.0(13) . . . . ? C16 C15 C14 O3 178.2(8) . . . . ? C13 O3 C14 C19 -174.3(8) . . . . ? C13 O3 C14 C15 7.5(12) . . . . ? C66 N6 C44 C43 -160.0(7) . . . . ? C55 N6 C44 C43 71.1(8) . . . . ? C8 C7 C6 C5 -1.2(14) . . . . ? C4 C5 C6 C7 -0.1(14) . . . . ? C42 O6 C43 C44 -169.1(7) . . . . ? N6 C44 C43 O6 -102.0(8) . . . . ? C42 C37 C38 C39 0.8(14) . . . . ? C36 C37 C38 C39 -179.2(10) . . . . ? C23 N2 C12 C13 156.8(8) . . . . ? C11 N2 C12 C13 -73.5(10) . . . . ? O3 C13 C12 N2 120.5(9) . . . . ? C37 C38 C39 C40 1.6(16) . . . . ? C22 N1 C33 C32 -155.5(7) . . . . ? C1 N1 C33 C32 81.2(9) . . . . ? N4 C32 C33 N1 145.6(7) . . . . ? O2 C25 C30 C29 176.0(9) . . . . ? C26 C25 C30 C29 1.3(14) . . . . ? O2 C25 C30 C31 -5.5(13) . . . . ? C26 C25 C30 C31 179.9(9) . . . . ? N4 C31 C30 C29 96.0(10) . . . . ? N4 C31 C30 C25 -82.6(10) . . . . ? C56 N7 C34 C35 -72.6(9) . . . . ? C45 N7 C34 C35 166.4(7) . . . . ? N10 C35 C34 N7 -75.7(9) . . . . ? C26 C27 C28 C29 -2.6(19) . . . . ? C27 C28 C29 C30 0.6(18) . . . . ? C25 C30 C29 C28 0.1(15) . . . . ? C31 C30 C29 C28 -178.5(9) . . . . ? C38 C39 C40 C41 -2.4(16) . . . . ? C42 C41 C40 C39 0.8(15) . . . . ? O2 C25 C26 C27 -177.4(9) . . . . ? C30 C25 C26 C27 -3.1(14) . . . . ? C28 C27 C26 C25 3.8(17) . . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 28.45 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.757 _refine_diff_density_min -0.489 _refine_diff_density_rms 0.174 data_Complex3 #TrackingRef 'B924157D_ccdc_754955_754960_cif.txt' _database_code_depnum_ccdc_archive 'CCDC 754957' #TrackingRef 'Complex1-6.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C33 H57 Cl4 N5 O23' _chemical_formula_sum 'C33 H57 Cl4 N5 O23' _chemical_formula_weight 1033.64 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 Monoclinic _symmetry_space_group_name_H-M 'P 21/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 13.327(5) _cell_length_b 12.267(3) _cell_length_c 28.121(6) _cell_angle_alpha 90.00 _cell_angle_beta 103.374(6) _cell_angle_gamma 90.00 _cell_volume 4473(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(1) _cell_measurement_reflns_used ? _cell_measurement_theta_min 2.3 _cell_measurement_theta_max 28.4 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.535 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2168 _exptl_absorpt_coefficient_mu 0.355 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9323 _exptl_absorpt_correction_T_max 0.9421 _exptl_absorpt_process_details 'SADABAS 2.10 (Bruker 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(1) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX' _diffrn_measurement_method /w-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 29043 _diffrn_reflns_av_R_equivalents 0.0514 _diffrn_reflns_av_sigmaI/netI 0.0719 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 37 _diffrn_reflns_theta_min 2.23 _diffrn_reflns_theta_max 28.34 _reflns_number_total 11035 _reflns_number_gt 7005 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART 5.628 (Bruker, 2003)' _computing_cell_refinement 'SAINT 6.45 ( Bruker, 2003)' _computing_data_reduction 'SAINT 6.45 (Bruker, 2003)' _computing_structure_solution SIR-97 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Diamond 2.1e' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0938P)^2^+1.6183P] 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 11035 _refine_ls_number_parameters 610 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0958 _refine_ls_R_factor_gt 0.0607 _refine_ls_wR_factor_ref 0.1972 _refine_ls_wR_factor_gt 0.1585 _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_restrained_S_all 1.083 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.48012(7) 0.34648(7) 0.94752(3) 0.0267(2) Uani 1 1 d . . . Cl2 Cl 0.61382(7) 0.09221(7) 0.80115(3) 0.0275(2) Uani 1 1 d . . . Cl3 Cl 0.22099(8) 0.01232(8) 0.69027(4) 0.0332(2) Uani 1 1 d . . . Cl4 Cl 0.09038(8) -0.12013(8) 0.83818(4) 0.0343(2) Uani 1 1 d . . . O5 O 0.37603(19) 0.3469(2) 0.91629(9) 0.0254(6) Uani 1 1 d . . . O8 O 0.6932(2) 0.0108(2) 0.81444(11) 0.0352(7) Uani 1 1 d . . . O3 O 0.3237(2) 0.0670(2) 1.00344(9) 0.0270(6) Uani 1 1 d . . . O2 O 0.1700(2) 0.3446(2) 1.02045(10) 0.0302(6) Uani 1 1 d . . . O9 O 0.5253(2) 0.0487(3) 0.76783(11) 0.0392(8) Uani 1 1 d . . . O10 O 0.5856(2) 0.1291(2) 0.84468(11) 0.0332(7) Uani 1 1 d . . . O4 O 0.4758(2) 0.3129(2) 0.99536(10) 0.0333(7) Uani 1 1 d . . . O1 O 0.05847(19) 0.1146(2) 1.00849(10) 0.0284(6) Uani 1 1 d . . . C30 C 0.3462(3) 0.0151(3) 0.96424(13) 0.0208(7) Uani 1 1 d . . . O14 O 0.2340(3) 0.1231(3) 0.70103(14) 0.0337(5) Uani 1 1 d . . . O7 O 0.5418(2) 0.2719(3) 0.92704(11) 0.0301(5) Uani 1 1 d . . . N4 N 0.3198(2) 0.5670(2) 0.87910(11) 0.0251(7) Uani 1 1 d . . . H4A H 0.3829 0.5898 0.8771 0.030 Uiso 1 1 calc R . . H4B H 0.3237 0.4951 0.8854 0.030 Uiso 1 1 calc R . . N3 N -0.0383(2) 0.2674(3) 0.81143(12) 0.0291(7) Uani 1 1 d . . . H3A H -0.0448 0.2519 0.7796 0.035 Uiso 1 1 calc R . . H3B H -0.0771 0.3267 0.8131 0.035 Uiso 1 1 calc R . . O11 O 0.6548(2) 0.1821(2) 0.77883(11) 0.0346(8) Uani 1 1 d . . . O15 O 0.3047(3) -0.0487(4) 0.72028(13) 0.0333(6) Uani 1 1 d . . . O16 O 0.1443(3) -0.1448(3) 0.88651(13) 0.0323(5) Uani 1 1 d . . . O12 O 0.1267(3) -0.0246(3) 0.69989(16) 0.0348(6) Uani 1 1 d . . . N5 N 0.3741(2) 0.2014(2) 0.83562(11) 0.0225(6) Uani 1 1 d . . . H5A H 0.3543 0.2410 0.8588 0.027 Uiso 1 1 calc R . . H5B H 0.4424 0.1900 0.8456 0.027 Uiso 1 1 calc R . . OW3 O 0.4979(2) 0.1498(3) 0.63867(11) 0.0304(7) Uani 1 1 d . . . N1 N 0.2175(2) 0.3879(2) 0.80822(11) 0.0229(6) Uani 1 1 d . . . N2 N 0.2398(2) 0.1569(2) 1.07456(11) 0.0241(7) Uani 1 1 d . . . H2 H 0.2219 0.1644 1.0415 0.029 Uiso 1 1 calc R . . OW4 O 0.5080(3) 0.3108(3) 0.71147(11) 0.0339(7) Uani 1 1 d . . . O13 O 0.2215(3) -0.0078(3) 0.63996(12) 0.0367(5) Uani 1 1 d . . . O6 O 0.5203(3) 0.4549(2) 0.94817(11) 0.0324(8) Uani 1 1 d . . . OW2 O 0.4553(2) -0.0651(3) 0.66012(13) 0.0325(8) Uani 1 1 d . . . C31 C 0.3243(3) 0.0741(3) 0.92088(13) 0.0224(7) Uani 1 1 d . . . H31 H 0.2948 0.1430 0.9201 0.027 Uiso 1 1 calc R . . OW1 O -0.0054(3) -0.3507(3) 0.76629(14) 0.0308(8) Uani 1 1 d . . . C26 C 0.3460(3) 0.0312(3) 0.87868(13) 0.0232(7) Uani 1 1 d . . . O19 O 0.1401(3) -0.1731(3) 0.80457(15) 0.0351(8) Uani 1 1 d . . . O17 O 0.0907(3) -0.0058(3) 0.83018(17) 0.0333(6) Uani 1 1 d . . . C14 C 0.2899(3) 0.6249(3) 0.92090(13) 0.0254(8) Uani 1 1 d . . . H14A H 0.2676 0.6984 0.9110 0.031 Uiso 1 1 calc R . . H14B H 0.3494 0.6297 0.9483 0.031 Uiso 1 1 calc R . . C13 C 0.2462(3) 0.5853(3) 0.83076(14) 0.0266(8) Uani 1 1 d . . . H13A H 0.2616 0.6546 0.8174 0.032 Uiso 1 1 calc R . . H13B H 0.1765 0.5889 0.8355 0.032 Uiso 1 1 calc R . . O18 O -0.0137(2) -0.1603(3) 0.83046(12) 0.0323(7) Uani 1 1 d . . . C19 C 0.1520(3) 0.4231(3) 0.98488(13) 0.0244(8) Uani 1 1 d . . . C15 C 0.2041(3) 0.5649(3) 0.93653(13) 0.0242(8) Uani 1 1 d . . . C28 C 0.4087(3) -0.1311(3) 0.92344(14) 0.0243(8) Uani 1 1 d . . . H28 H 0.4370 -0.2005 0.9240 0.029 Uiso 1 1 calc R . . C11 C 0.1565(3) 0.0899(3) 1.08798(14) 0.0277(8) Uani 1 1 d . . . H11A H 0.1589 0.0983 1.1225 0.033 Uiso 1 1 calc R . . H11B H 0.1667 0.0135 1.0816 0.033 Uiso 1 1 calc R . . C20 C 0.2302(3) 0.4858(3) 0.97310(14) 0.0249(8) Uani 1 1 d . . . H20 H 0.2986 0.4751 0.9893 0.030 Uiso 1 1 calc R . . C27 C 0.3882(3) -0.0733(3) 0.88027(14) 0.0249(8) Uani 1 1 d . . . H27 H 0.4025 -0.1038 0.8523 0.030 Uiso 1 1 calc R . . C22 C 0.2483(3) 0.2710(3) 1.09525(14) 0.0265(8) Uani 1 1 d . . . H22A H 0.1857 0.2895 1.1055 0.032 Uiso 1 1 calc R . . H22B H 0.3056 0.2750 1.1236 0.032 Uiso 1 1 calc R . . C3 C -0.0815(3) 0.1736(3) 0.83470(15) 0.0298(8) Uani 1 1 d . . . H3C H -0.0394 0.1097 0.8333 0.036 Uiso 1 1 calc R . . H3D H -0.1504 0.1580 0.8155 0.036 Uiso 1 1 calc R . . C12 C 0.2525(3) 0.4954(3) 0.79466(14) 0.0261(8) Uani 1 1 d . . . H12A H 0.2110 0.5158 0.7628 0.031 Uiso 1 1 calc R . . H12B H 0.3234 0.4890 0.7918 0.031 Uiso 1 1 calc R . . C4 C -0.0872(3) 0.1913(3) 0.88703(14) 0.0267(8) Uani 1 1 d . . . C9 C -0.0103(3) 0.1519(3) 0.92531(15) 0.0268(8) Uani 1 1 d . . . H9 H 0.0491 0.1216 0.9188 0.032 Uiso 1 1 calc R . . C29 C 0.3887(3) -0.0893(3) 0.96584(14) 0.0248(8) Uani 1 1 d . . . H29 H 0.4031 -0.1295 0.9947 0.030 Uiso 1 1 calc R . . C16 C 0.1017(3) 0.5832(3) 0.91380(14) 0.0272(8) Uani 1 1 d . . . H16 H 0.0841 0.6388 0.8909 0.033 Uiso 1 1 calc R . . C1 C 0.1051(3) 0.3873(3) 0.80346(13) 0.0240(8) Uani 1 1 d . . . H1A H 0.0706 0.3786 0.7693 0.029 Uiso 1 1 calc R . . H1B H 0.0841 0.4567 0.8145 0.029 Uiso 1 1 calc R . . C24 C 0.3541(3) 0.2664(3) 0.78940(13) 0.0261(8) Uani 1 1 d . . . H24A H 0.3686 0.2216 0.7634 0.031 Uiso 1 1 calc R . . H24B H 0.4005 0.3284 0.7937 0.031 Uiso 1 1 calc R . . C25 C 0.3199(3) 0.0931(3) 0.83136(13) 0.0249(8) Uani 1 1 d . . . H25A H 0.2459 0.1047 0.8219 0.030 Uiso 1 1 calc R . . H25B H 0.3396 0.0502 0.8060 0.030 Uiso 1 1 calc R . . C8 C -0.0215(3) 0.1573(3) 0.97329(14) 0.0264(8) Uani 1 1 d . . . C21 C 0.2646(3) 0.3498(3) 1.05728(14) 0.0286(8) Uani 1 1 d . . . H21A H 0.2766 0.4228 1.0706 0.034 Uiso 1 1 calc R . . H21B H 0.3228 0.3283 1.0441 0.034 Uiso 1 1 calc R . . C33 C 0.3436(3) 0.1019(3) 1.08622(14) 0.0257(8) Uani 1 1 d . . . H33A H 0.3968 0.1557 1.0860 0.031 Uiso 1 1 calc R . . H33B H 0.3561 0.0708 1.1188 0.031 Uiso 1 1 calc R . . C18 C 0.0500(3) 0.4378(3) 0.96023(14) 0.0266(8) Uani 1 1 d . . . H18 H -0.0013 0.3935 0.9673 0.032 Uiso 1 1 calc R . . C6 C -0.1853(3) 0.2439(3) 0.94519(15) 0.0299(7) Uani 1 1 d . . . H6 H -0.2436 0.2764 0.9518 0.036 Uiso 1 1 calc R . . C32 C 0.3502(3) 0.0135(3) 1.05016(13) 0.0249(8) Uani 1 1 d . . . H32A H 0.4193 -0.0165 1.0562 0.030 Uiso 1 1 calc R . . H32B H 0.3020 -0.0448 1.0519 0.030 Uiso 1 1 calc R . . C17 C 0.0251(3) 0.5180(3) 0.92534(14) 0.0273(8) Uani 1 1 d . . . H17 H -0.0435 0.5289 0.9093 0.033 Uiso 1 1 calc R . . C2 C 0.0722(3) 0.2957(3) 0.83314(14) 0.0257(8) Uani 1 1 d . . . H2A H 0.1154 0.2322 0.8328 0.031 Uiso 1 1 calc R . . H2B H 0.0801 0.3187 0.8668 0.031 Uiso 1 1 calc R . . C23 C 0.2440(3) 0.3066(3) 0.77470(13) 0.0248(8) Uani 1 1 d . . . H23A H 0.2324 0.3382 0.7423 0.030 Uiso 1 1 calc R . . H23B H 0.1980 0.2447 0.7729 0.030 Uiso 1 1 calc R . . C5 C -0.1754(3) 0.2380(3) 0.89744(15) 0.0283(8) Uani 1 1 d . . . H5 H -0.2273 0.2651 0.8722 0.034 Uiso 1 1 calc R . . C10 C 0.0529(3) 0.1272(3) 1.05810(14) 0.0293(8) Uani 1 1 d . . . H10A H -0.0022 0.0829 1.0652 0.035 Uiso 1 1 calc R . . H10B H 0.0405 0.2028 1.0651 0.035 Uiso 1 1 calc R . . C7 C -0.1100(3) 0.2024(3) 0.98357(15) 0.0292(8) Uani 1 1 d . . . H7 H -0.1185 0.2047 1.0155 0.035 Uiso 1 1 calc R . . H1W3 H 0.475(4) 0.093(2) 0.6480(16) 0.050 Uiso 1 1 d . . . H2W3 H 0.502(4) 0.194(3) 0.6614(13) 0.050 Uiso 1 1 d . . . H1W4 H 0.497(4) 0.375(2) 0.719(2) 0.081 Uiso 1 1 d . . . H2W4 H 0.556(3) 0.287(4) 0.7332(15) 0.062 Uiso 1 1 d . . . H1W1 H -0.048(3) -0.398(3) 0.7546(15) 0.050 Uiso 1 1 d . . . H1W2 H 0.419(3) -0.081(4) 0.6323(9) 0.050 Uiso 1 1 d . . . H2W1 H -0.018(4) -0.329(4) 0.7915(12) 0.050 Uiso 1 1 d . . . H2W2 H 0.409(3) -0.059(4) 0.6762(13) 0.050 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 0.0278(5) 0.0266(4) 0.0227(4) -0.0027(3) 0.0001(3) 0.0009(3) Cl2 0.0269(5) 0.0288(5) 0.0271(5) 0.0029(4) 0.0069(4) 0.0021(4) Cl3 0.0379(6) 0.0303(5) 0.0300(5) -0.0026(4) 0.0047(4) -0.0081(4) Cl4 0.0303(5) 0.0317(5) 0.0417(6) 0.0055(4) 0.0100(4) 0.0040(4) O5 0.0249(13) 0.0243(13) 0.0243(13) -0.0015(10) 0.0001(10) 0.0051(10) O8 0.0401(12) 0.0354(12) 0.0269(12) 0.0081(11) 0.0041(11) 0.0011(10) O3 0.0359(15) 0.0253(13) 0.0200(13) 0.0043(10) 0.0067(11) 0.0051(11) O2 0.0269(14) 0.0289(14) 0.0321(15) -0.0001(12) 0.0011(11) -0.0048(11) O9 0.0424(12) 0.0388(12) 0.0305(13) -0.0025(10) -0.0011(12) -0.0033(10) O10 0.0357(15) 0.0274(14) 0.0355(14) -0.0061(14) 0.0048(12) 0.0020(13) O4 0.0428(17) 0.0321(15) 0.0228(14) 0.0045(11) 0.0030(12) 0.0018(12) O1 0.0212(13) 0.0313(14) 0.0326(15) -0.0018(12) 0.0062(11) -0.0008(11) C30 0.0208(11) 0.0173(11) 0.0254(12) -0.0038(10) 0.0078(10) -0.0010(10) O14 0.039(3) 0.0343(18) 0.028(3) -0.0053(17) 0.006(2) -0.002(2) O7 0.0287(15) 0.033(2) 0.0261(17) 0.0077(15) 0.0036(13) 0.0021(14) N4 0.0248(16) 0.0205(15) 0.0308(17) 0.0026(13) 0.0015(13) -0.0018(12) N3 0.0248(16) 0.0318(17) 0.0282(17) 0.0029(14) 0.0010(13) -0.0012(13) O11 0.0377(17) 0.0372(16) 0.0280(19) 0.0079(14) 0.0042(14) 0.0001(13) O15 0.040(2) 0.033(3) 0.026(2) 0.010(2) 0.0056(16) 0.002(2) O16 0.0353(13) 0.032(3) 0.027(2) 0.006(2) 0.0042(12) -0.0049(12) O12 0.041(2) 0.036(2) 0.025(3) -0.005(2) 0.005(2) -0.0022(16) N5 0.0226(15) 0.0215(14) 0.0237(15) -0.0023(12) 0.0057(12) 0.0016(12) OW3 0.0302(16) 0.0328(17) 0.0293(17) 0.0011(14) 0.0063(13) 0.0020(14) N1 0.0233(15) 0.0207(14) 0.0246(16) 0.0025(12) 0.0056(12) 0.0002(12) N2 0.0231(16) 0.0246(15) 0.0241(16) 0.0004(13) 0.0042(12) -0.0020(12) OW4 0.030(2) 0.0368(17) 0.0328(18) 0.0076(14) 0.0055(14) 0.0034(15) O13 0.031(2) 0.040(2) 0.0370(18) -0.0056(16) 0.0059(15) 0.0018(17) O6 0.035(2) 0.0356(16) 0.0212(18) 0.0024(14) -0.0043(15) -0.0019(15) OW2 0.0334(19) 0.030(2) 0.0345(19) 0.0053(18) 0.0044(15) 0.0018(17) C31 0.0199(17) 0.0174(16) 0.0292(19) -0.0013(14) 0.0044(14) 0.0019(13) OW1 0.036(2) 0.0308(18) 0.027(2) 0.0076(16) 0.0078(18) 0.0012(15) C26 0.0213(17) 0.0231(17) 0.0253(18) -0.0041(15) 0.0057(14) -0.0020(14) O19 0.038(2) 0.033(2) 0.032(3) -0.006(2) 0.005(2) 0.0008(19) O17 0.041(2) 0.0283(17) 0.028(4) 0.010(2) 0.006(2) 0.0024(15) C14 0.0235(18) 0.0243(18) 0.0266(19) -0.0001(15) 0.0029(15) -0.0025(14) C13 0.0261(19) 0.0255(18) 0.028(2) 0.0028(15) 0.0057(15) -0.0011(15) O18 0.0361(13) 0.033(2) 0.0268(13) -0.0050(12) 0.0065(11) -0.0026(11) C19 0.0290(14) 0.0213(14) 0.0233(15) -0.0027(14) 0.0072(12) -0.0004(12) C15 0.0238(13) 0.0219(13) 0.0256(13) -0.0043(12) 0.0029(11) -0.0021(11) C28 0.0198(17) 0.0176(16) 0.036(2) -0.0022(15) 0.0071(15) -0.0016(13) C11 0.0247(19) 0.031(2) 0.030(2) 0.0051(16) 0.0121(15) -0.0047(15) C20 0.0207(18) 0.0247(18) 0.0287(19) -0.0052(15) 0.0044(14) -0.0025(14) C27 0.0229(18) 0.0251(18) 0.0268(19) -0.0046(15) 0.0056(15) -0.0021(14) C22 0.0231(19) 0.0286(19) 0.0264(19) -0.0053(16) 0.0029(15) -0.0028(15) C3 0.028(2) 0.0261(19) 0.035(2) -0.0006(16) 0.0064(16) -0.0033(15) C12 0.0257(19) 0.0259(18) 0.0276(19) 0.0049(15) 0.0080(15) 0.0004(15) C4 0.0255(19) 0.0181(16) 0.036(2) -0.0023(15) 0.0058(16) -0.0046(14) C9 0.0210(18) 0.0206(17) 0.040(2) -0.0011(16) 0.0088(16) -0.0014(14) C29 0.0208(18) 0.0235(17) 0.030(2) 0.0033(15) 0.0055(15) -0.0015(14) C16 0.0248(19) 0.0243(18) 0.030(2) -0.0012(16) 0.0052(16) 0.0054(14) C1 0.0228(18) 0.0228(17) 0.0253(18) 0.0038(15) 0.0032(14) 0.0021(14) C24 0.0268(19) 0.0289(19) 0.0220(18) -0.0022(15) 0.0047(15) -0.0020(15) C25 0.0269(19) 0.0256(18) 0.0207(18) -0.0020(14) 0.0022(14) -0.0013(14) C8 0.0174(17) 0.0244(18) 0.034(2) -0.0016(16) 0.0000(15) -0.0031(14) C21 0.0238(19) 0.031(2) 0.029(2) -0.0037(16) 0.0031(15) -0.0034(15) C33 0.0219(18) 0.0283(19) 0.0255(19) 0.0031(15) 0.0028(14) 0.0009(14) C18 0.0251(19) 0.0291(19) 0.0276(19) -0.0043(16) 0.0099(15) -0.0032(15) C6 0.0218(19) 0.0252(19) 0.043(2) -0.0014(17) 0.0074(16) -0.0009(15) C32 0.0240(18) 0.0286(19) 0.0208(17) 0.0046(15) 0.0027(14) -0.0002(15) C17 0.0210(18) 0.0277(19) 0.033(2) -0.0076(16) 0.0055(15) 0.0011(15) C2 0.0192(18) 0.0283(18) 0.0285(19) 0.0001(16) 0.0031(14) -0.0022(14) C23 0.0258(19) 0.0288(18) 0.0173(17) 0.0014(15) 0.0002(14) -0.0018(15) C5 0.0211(18) 0.0225(18) 0.039(2) 0.0020(16) 0.0020(16) -0.0012(14) C10 0.0234(19) 0.030(2) 0.034(2) 0.0022(17) 0.0056(16) -0.0015(15) C7 0.0229(19) 0.0274(19) 0.037(2) -0.0029(17) 0.0071(16) -0.0044(15) _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 Cl1 O4 1.421(3) . ? Cl1 O6 1.433(3) . ? Cl1 O7 1.436(3) . ? Cl1 O5 1.460(3) . ? Cl2 O9 1.429(3) . ? Cl2 O10 1.434(3) . ? Cl2 O11 1.437(3) . ? Cl2 O8 1.440(3) . ? Cl3 O14 1.395(3) . ? Cl3 O12 1.419(3) . ? Cl3 O13 1.438(3) . ? Cl3 O15 1.443(4) . ? Cl4 O16 1.416(4) . ? Cl4 O17 1.420(3) . ? Cl4 O19 1.430(4) . ? Cl4 O18 1.440(3) . ? O3 C30 1.365(4) . ? O3 C32 1.438(4) . ? O2 C19 1.369(4) . ? O2 C21 1.436(4) . ? O1 C8 1.379(4) . ? O1 C10 1.423(5) . ? C30 C31 1.390(5) . ? C30 C29 1.397(5) . ? N4 C13 1.497(5) . ? N4 C14 1.503(5) . ? N4 H4A 0.9000 . ? N4 H4B 0.9000 . ? N3 C2 1.499(5) . ? N3 C3 1.503(5) . ? N3 H3A 0.9000 . ? N3 H3B 0.9000 . ? N5 C24 1.495(5) . ? N5 C25 1.505(5) . ? N5 H5A 0.9000 . ? N5 H5B 0.9000 . ? OW3 H1W3 0.82(4) . ? OW3 H2W3 0.83(4) . ? N1 C23 1.471(5) . ? N1 C1 1.472(5) . ? N1 C12 1.478(5) . ? N2 C11 1.498(5) . ? N2 C33 1.505(5) . ? N2 C22 1.511(5) . ? N2 H2 0.9100 . ? OW4 H1W4 0.83(5) . ? OW4 H2W4 0.83(4) . ? OW2 H1W2 0.84(4) . ? OW2 H2W2 0.85(4) . ? C31 C26 1.389(5) . ? C31 H31 0.9300 . ? OW1 H1W1 0.83(4) . ? OW1 H2W1 0.81(4) . ? C26 C27 1.397(5) . ? C26 C25 1.501(5) . ? C14 C15 1.508(5) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C13 C12 1.515(5) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C19 C18 1.387(5) . ? C19 C20 1.395(5) . ? C15 C16 1.385(5) . ? C15 C20 1.398(5) . ? C28 C27 1.377(5) . ? C28 C29 1.380(5) . ? C28 H28 0.9300 . ? C11 C10 1.512(5) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C20 H20 0.9300 . ? C27 H27 0.9300 . ? C22 C21 1.493(5) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C3 C4 1.507(6) . ? C3 H3C 0.9700 . ? C3 H3D 0.9700 . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C4 C9 1.390(5) . ? C4 C5 1.398(5) . ? C9 C8 1.393(6) . ? C9 H9 0.9300 . ? C29 H29 0.9300 . ? C16 C17 1.393(5) . ? C16 H16 0.9300 . ? C1 C2 1.524(5) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C24 C23 1.512(5) . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C8 C7 1.392(5) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C33 C32 1.500(5) . ? C33 H33A 0.9700 . ? C33 H33B 0.9700 . ? C18 C17 1.375(5) . ? C18 H18 0.9300 . ? C6 C5 1.381(6) . ? C6 C7 1.389(5) . ? C6 H6 0.9300 . ? C32 H32A 0.9700 . ? C32 H32B 0.9700 . ? C17 H17 0.9300 . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C5 H5 0.9300 . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C7 H7 0.9300 . ? 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 O4 Cl1 O6 110.74(18) . . ? O4 Cl1 O7 110.33(18) . . ? O6 Cl1 O7 110.4(2) . . ? O4 Cl1 O5 109.24(17) . . ? O6 Cl1 O5 107.76(17) . . ? O7 Cl1 O5 108.24(16) . . ? O9 Cl2 O10 109.73(19) . . ? O9 Cl2 O11 109.83(19) . . ? O10 Cl2 O11 109.4(2) . . ? O9 Cl2 O8 110.9(2) . . ? O10 Cl2 O8 108.60(17) . . ? O11 Cl2 O8 108.38(18) . . ? O14 Cl3 O12 109.9(2) . . ? O14 Cl3 O13 110.6(2) . . ? O12 Cl3 O13 109.8(2) . . ? O14 Cl3 O15 109.8(3) . . ? O12 Cl3 O15 108.8(2) . . ? O13 Cl3 O15 107.9(2) . . ? O16 Cl4 O17 110.1(3) . . ? O16 Cl4 O19 109.1(2) . . ? O17 Cl4 O19 109.0(3) . . ? O16 Cl4 O18 109.2(2) . . ? O17 Cl4 O18 110.6(2) . . ? O19 Cl4 O18 108.8(2) . . ? C30 O3 C32 118.1(3) . . ? C19 O2 C21 118.2(3) . . ? C8 O1 C10 117.1(3) . . ? O3 C30 C31 115.1(3) . . ? O3 C30 C29 124.4(3) . . ? C31 C30 C29 120.5(3) . . ? C13 N4 C14 113.8(3) . . ? C13 N4 H4A 108.8 . . ? C14 N4 H4A 108.8 . . ? C13 N4 H4B 108.8 . . ? C14 N4 H4B 108.8 . . ? H4A N4 H4B 107.7 . . ? C2 N3 C3 116.0(3) . . ? C2 N3 H3A 108.3 . . ? C3 N3 H3A 108.3 . . ? C2 N3 H3B 108.3 . . ? C3 N3 H3B 108.3 . . ? H3A N3 H3B 107.4 . . ? C24 N5 C25 114.6(3) . . ? C24 N5 H5A 108.6 . . ? C25 N5 H5A 108.6 . . ? C24 N5 H5B 108.6 . . ? C25 N5 H5B 108.6 . . ? H5A N5 H5B 107.6 . . ? H1W3 OW3 H2W3 105(3) . . ? C23 N1 C1 109.2(3) . . ? C23 N1 C12 107.6(3) . . ? C1 N1 C12 110.9(3) . . ? C11 N2 C33 113.4(3) . . ? C11 N2 C22 113.9(3) . . ? C33 N2 C22 110.4(3) . . ? C11 N2 H2 106.2 . . ? C33 N2 H2 106.2 . . ? C22 N2 H2 106.2 . . ? H1W4 OW4 H2W4 107(3) . . ? H1W2 OW2 H2W2 101(3) . . ? C26 C31 C30 120.6(3) . . ? C26 C31 H31 119.7 . . ? C30 C31 H31 119.7 . . ? H1W1 OW1 H2W1 108(3) . . ? C31 C26 C27 118.9(3) . . ? C31 C26 C25 121.0(3) . . ? C27 C26 C25 120.1(3) . . ? N4 C14 C15 110.7(3) . . ? N4 C14 H14A 109.5 . . ? C15 C14 H14A 109.5 . . ? N4 C14 H14B 109.5 . . ? C15 C14 H14B 109.5 . . ? H14A C14 H14B 108.1 . . ? N4 C13 C12 111.9(3) . . ? N4 C13 H13A 109.2 . . ? C12 C13 H13A 109.2 . . ? N4 C13 H13B 109.2 . . ? C12 C13 H13B 109.2 . . ? H13A C13 H13B 107.9 . . ? O2 C19 C18 116.3(3) . . ? O2 C19 C20 123.1(3) . . ? C18 C19 C20 120.6(3) . . ? C16 C15 C20 120.2(4) . . ? C16 C15 C14 121.3(3) . . ? C20 C15 C14 118.5(3) . . ? C27 C28 C29 122.2(3) . . ? C27 C28 H28 118.9 . . ? C29 C28 H28 118.9 . . ? N2 C11 C10 109.2(3) . . ? N2 C11 H11A 109.8 . . ? C10 C11 H11A 109.8 . . ? N2 C11 H11B 109.8 . . ? C10 C11 H11B 109.8 . . ? H11A C11 H11B 108.3 . . ? C19 C20 C15 119.0(3) . . ? C19 C20 H20 120.5 . . ? C15 C20 H20 120.5 . . ? C28 C27 C26 119.8(3) . . ? C28 C27 H27 120.1 . . ? C26 C27 H27 120.1 . . ? C21 C22 N2 109.6(3) . . ? C21 C22 H22A 109.8 . . ? N2 C22 H22A 109.8 . . ? C21 C22 H22B 109.8 . . ? N2 C22 H22B 109.8 . . ? H22A C22 H22B 108.2 . . ? N3 C3 C4 115.2(3) . . ? N3 C3 H3C 108.5 . . ? C4 C3 H3C 108.5 . . ? N3 C3 H3D 108.5 . . ? C4 C3 H3D 108.5 . . ? H3C C3 H3D 107.5 . . ? N1 C12 C13 114.0(3) . . ? N1 C12 H12A 108.8 . . ? C13 C12 H12A 108.8 . . ? N1 C12 H12B 108.8 . . ? C13 C12 H12B 108.8 . . ? H12A C12 H12B 107.6 . . ? C9 C4 C5 119.0(4) . . ? C9 C4 C3 120.8(3) . . ? C5 C4 C3 119.9(3) . . ? C4 C9 C8 120.6(4) . . ? C4 C9 H9 119.7 . . ? C8 C9 H9 119.7 . . ? C28 C29 C30 118.1(3) . . ? C28 C29 H29 121.0 . . ? C30 C29 H29 121.0 . . ? C15 C16 C17 119.8(4) . . ? C15 C16 H16 120.1 . . ? C17 C16 H16 120.1 . . ? N1 C1 C2 111.7(3) . . ? N1 C1 H1A 109.3 . . ? C2 C1 H1A 109.3 . . ? N1 C1 H1B 109.3 . . ? C2 C1 H1B 109.3 . . ? H1A C1 H1B 107.9 . . ? N5 C24 C23 112.2(3) . . ? N5 C24 H24A 109.2 . . ? C23 C24 H24A 109.2 . . ? N5 C24 H24B 109.2 . . ? C23 C24 H24B 109.2 . . ? H24A C24 H24B 107.9 . . ? C26 C25 N5 111.6(3) . . ? C26 C25 H25A 109.3 . . ? N5 C25 H25A 109.3 . . ? C26 C25 H25B 109.3 . . ? N5 C25 H25B 109.3 . . ? H25A C25 H25B 108.0 . . ? O1 C8 C7 123.6(4) . . ? O1 C8 C9 116.1(3) . . ? C7 C8 C9 120.3(3) . . ? O2 C21 C22 103.8(3) . . ? O2 C21 H21A 111.0 . . ? C22 C21 H21A 111.0 . . ? O2 C21 H21B 111.0 . . ? C22 C21 H21B 111.0 . . ? H21A C21 H21B 109.0 . . ? C32 C33 N2 111.8(3) . . ? C32 C33 H33A 109.3 . . ? N2 C33 H33A 109.3 . . ? C32 C33 H33B 109.3 . . ? N2 C33 H33B 109.3 . . ? H33A C33 H33B 107.9 . . ? C17 C18 C19 119.8(4) . . ? C17 C18 H18 120.1 . . ? C19 C18 H18 120.1 . . ? C5 C6 C7 121.4(4) . . ? C5 C6 H6 119.3 . . ? C7 C6 H6 119.3 . . ? O3 C32 C33 104.3(3) . . ? O3 C32 H32A 110.9 . . ? C33 C32 H32A 110.9 . . ? O3 C32 H32B 110.9 . . ? C33 C32 H32B 110.9 . . ? H32A C32 H32B 108.9 . . ? C18 C17 C16 120.5(3) . . ? C18 C17 H17 119.7 . . ? C16 C17 H17 119.7 . . ? N3 C2 C1 109.2(3) . . ? N3 C2 H2A 109.9 . . ? C1 C2 H2A 109.9 . . ? N3 C2 H2B 109.9 . . ? C1 C2 H2B 109.9 . . ? H2A C2 H2B 108.3 . . ? N1 C23 C24 114.1(3) . . ? N1 C23 H23A 108.7 . . ? C24 C23 H23A 108.7 . . ? N1 C23 H23B 108.7 . . ? C24 C23 H23B 108.7 . . ? H23A C23 H23B 107.6 . . ? C6 C5 C4 120.0(3) . . ? C6 C5 H5 120.0 . . ? C4 C5 H5 120.0 . . ? O1 C10 C11 105.3(3) . . ? O1 C10 H10A 110.7 . . ? C11 C10 H10A 110.7 . . ? O1 C10 H10B 110.7 . . ? C11 C10 H10B 110.7 . . ? H10A C10 H10B 108.8 . . ? C6 C7 C8 118.6(4) . . ? C6 C7 H7 120.7 . . ? C8 C7 H7 120.7 . . ? 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 C32 O3 C30 C31 -176.3(3) . . . . ? C32 O3 C30 C29 3.4(5) . . . . ? O3 C30 C31 C26 178.5(3) . . . . ? C29 C30 C31 C26 -1.2(5) . . . . ? C30 C31 C26 C27 1.4(5) . . . . ? C30 C31 C26 C25 178.3(3) . . . . ? C13 N4 C14 C15 77.4(4) . . . . ? C14 N4 C13 C12 -157.3(3) . . . . ? C21 O2 C19 C18 -159.6(3) . . . . ? C21 O2 C19 C20 20.7(5) . . . . ? N4 C14 C15 C16 -85.9(4) . . . . ? N4 C14 C15 C20 90.9(4) . . . . ? C33 N2 C11 C10 -157.6(3) . . . . ? C22 N2 C11 C10 75.1(4) . . . . ? O2 C19 C20 C15 -179.3(3) . . . . ? C18 C19 C20 C15 1.0(5) . . . . ? C16 C15 C20 C19 2.4(5) . . . . ? C14 C15 C20 C19 -174.4(3) . . . . ? C29 C28 C27 C26 0.1(5) . . . . ? C31 C26 C27 C28 -0.8(5) . . . . ? C25 C26 C27 C28 -177.8(3) . . . . ? C11 N2 C22 C21 -137.8(3) . . . . ? C33 N2 C22 C21 93.3(3) . . . . ? C2 N3 C3 C4 64.4(4) . . . . ? C23 N1 C12 C13 -170.8(3) . . . . ? C1 N1 C12 C13 69.9(4) . . . . ? N4 C13 C12 N1 66.4(4) . . . . ? N3 C3 C4 C9 -97.3(4) . . . . ? N3 C3 C4 C5 89.3(4) . . . . ? C5 C4 C9 C8 0.9(5) . . . . ? C3 C4 C9 C8 -172.5(3) . . . . ? C27 C28 C29 C30 0.0(5) . . . . ? O3 C30 C29 C28 -179.1(3) . . . . ? C31 C30 C29 C28 0.5(5) . . . . ? C20 C15 C16 C17 -3.9(5) . . . . ? C14 C15 C16 C17 172.9(3) . . . . ? C23 N1 C1 C2 81.6(4) . . . . ? C12 N1 C1 C2 -160.0(3) . . . . ? C25 N5 C24 C23 68.5(4) . . . . ? C31 C26 C25 N5 59.8(4) . . . . ? C27 C26 C25 N5 -123.3(4) . . . . ? C24 N5 C25 C26 178.3(3) . . . . ? C10 O1 C8 C7 -6.0(5) . . . . ? C10 O1 C8 C9 174.9(3) . . . . ? C4 C9 C8 O1 179.1(3) . . . . ? C4 C9 C8 C7 0.0(5) . . . . ? C19 O2 C21 C22 167.4(3) . . . . ? N2 C22 C21 O2 65.9(4) . . . . ? C11 N2 C33 C32 75.7(4) . . . . ? C22 N2 C33 C32 -155.1(3) . . . . ? O2 C19 C18 C17 177.4(3) . . . . ? C20 C19 C18 C17 -2.9(5) . . . . ? C30 O3 C32 C33 164.7(3) . . . . ? N2 C33 C32 O3 55.1(4) . . . . ? C19 C18 C17 C16 1.4(5) . . . . ? C15 C16 C17 C18 2.0(6) . . . . ? C3 N3 C2 C1 176.6(3) . . . . ? N1 C1 C2 N3 -155.7(3) . . . . ? C1 N1 C23 C24 -156.6(3) . . . . ? C12 N1 C23 C24 82.9(4) . . . . ? N5 C24 C23 N1 67.1(4) . . . . ? C7 C6 C5 C4 -1.2(6) . . . . ? C9 C4 C5 C6 -0.3(5) . . . . ? C3 C4 C5 C6 173.2(3) . . . . ? C8 O1 C10 C11 -171.2(3) . . . . ? N2 C11 C10 O1 57.9(4) . . . . ? C5 C6 C7 C8 2.1(6) . . . . ? O1 C8 C7 C6 179.5(3) . . . . ? C9 C8 C7 C6 -1.5(5) . . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 28.34 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.609 _refine_diff_density_min -0.486 _refine_diff_density_rms 0.114 data_Complex4 #TrackingRef 'B924157D_ccdc_754955_754960_cif.txt' _database_code_depnum_ccdc_archive 'CCDC 754958' #TrackingRef 'Complex1-6.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C33 H61 Cl2 N5 O13 S' _chemical_formula_sum 'C33 H61 Cl2 N5 O13 S' _chemical_formula_weight 838.83 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' S S 0.1246 0.1234 '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 Monoclinic _symmetry_space_group_name_H-M 'P 21/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 9.465(4) _cell_length_b 26.756(6) _cell_length_c 16.270(5) _cell_angle_alpha 90.00 _cell_angle_beta 93.333(6) _cell_angle_gamma 90.00 _cell_volume 4113(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(1) _cell_measurement_reflns_used ? _cell_measurement_theta_min 2.3 _cell_measurement_theta_max 28.4 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.355 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1792 _exptl_absorpt_coefficient_mu 0.275 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9445 _exptl_absorpt_correction_T_max 0.9522 _exptl_absorpt_process_details 'SADABS 2.10 (Bruker 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(1) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX' _diffrn_measurement_method /w-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 27160 _diffrn_reflns_av_R_equivalents 0.0609 _diffrn_reflns_av_sigmaI/netI 0.0706 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -34 _diffrn_reflns_limit_k_max 35 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 28.35 _reflns_number_total 10173 _reflns_number_gt 6693 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0432P)^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 10173 _refine_ls_number_parameters 535 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0945 _refine_ls_R_factor_gt 0.0526 _refine_ls_wR_factor_ref 0.2054 _refine_ls_wR_factor_gt 0.1522 _refine_ls_goodness_of_fit_ref 1.115 _refine_ls_restrained_S_all 1.115 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.09705(8) 0.19183(3) 0.15658(5) 0.02117(19) Uani 1 1 d . . . Cl2 Cl 0.08593(9) 0.08786(3) -0.13767(5) 0.0260(2) Uani 1 1 d . . . S1 S 0.38180(8) -0.06922(3) -0.28147(5) 0.01927(19) Uani 1 1 d . . . O4 O 0.5246(2) -0.09028(7) -0.29105(13) 0.0202(5) Uani 1 1 d . . . O5 O 0.3452(2) -0.07546(8) -0.19554(14) 0.0266(5) Uani 1 1 d . . . O6 O 0.2779(2) -0.09651(9) -0.33615(14) 0.0271(5) Uani 1 1 d . . . O7 O 0.3825(2) -0.01608(8) -0.30339(16) 0.0305(6) Uani 1 1 d . . . O1 O -0.0310(2) 0.33363(8) 0.04807(13) 0.0257(5) Uani 1 1 d . . . OW5 O 0.6772(3) -0.02056(9) -0.38852(17) 0.0308(6) Uani 1 1 d . . . O2 O 0.0518(2) 0.33469(8) 0.29638(14) 0.0259(5) Uani 1 1 d . . . O3 O 0.3516(2) 0.32694(8) 0.13429(15) 0.0264(5) Uani 1 1 d . . . N5 N 0.3635(3) 0.12200(9) 0.13865(15) 0.0194(5) Uani 1 1 d . . . H5A H 0.2816 0.1380 0.1461 0.023 Uiso 1 1 calc R . . H5B H 0.4099 0.1185 0.1882 0.023 Uiso 1 1 calc R . . OW3 O 0.8645(3) 0.05024(10) -0.53443(16) 0.0316(6) Uani 1 1 d . . . OW2 O 0.1920(3) 0.05871(10) -0.31475(15) 0.0305(6) Uani 1 1 d . . . OW1 O 0.3321(3) 0.00860(10) -0.09835(16) 0.0289(6) Uani 1 1 d . . . OW6 O 0.5924(3) 0.05069(10) -0.04556(18) 0.0308(6) Uani 1 1 d . . . N2 N 0.1274(3) 0.39520(9) 0.16247(16) 0.0218(6) Uani 1 1 d . . . N4 N -0.0165(3) 0.13016(9) 0.29942(15) 0.0193(5) Uani 1 1 d . . . H4A H -0.1105 0.1250 0.2991 0.023 Uiso 1 1 calc R . . H4B H 0.0015 0.1472 0.2535 0.023 Uiso 1 1 calc R . . N3 N -0.0591(3) 0.13140(9) 0.01460(16) 0.0194(5) Uani 1 1 d . . . H3A H -0.0026 0.1256 -0.0270 0.023 Uiso 1 1 calc R . . H3B H -0.0076 0.1474 0.0548 0.023 Uiso 1 1 calc R . . OW4 O 0.1492(3) 0.05731(10) -0.48465(17) 0.0295(6) Uani 1 1 d . . . N1 N 0.0900(2) 0.06438(9) 0.15039(15) 0.0179(5) Uani 1 1 d . . . H1 H 0.0984 0.0983 0.1496 0.021 Uiso 1 1 calc R . . C2 C -0.1095(3) 0.08281(11) 0.0469(2) 0.0222(7) Uani 1 1 d . . . H2A H -0.1685 0.0664 0.0043 0.027 Uiso 1 1 calc R . . H2B H -0.1672 0.0891 0.0931 0.027 Uiso 1 1 calc R . . C31 C 0.4086(3) 0.24324(11) 0.11180(19) 0.0209(6) Uani 1 1 d . . . H31 H 0.3215 0.2404 0.0826 0.025 Uiso 1 1 calc R . . C8 C -0.0590(3) 0.29927(11) -0.01384(19) 0.0206(6) Uani 1 1 d . . . C20 C 0.0317(3) 0.25104(11) 0.33561(19) 0.0206(6) Uani 1 1 d . . . H20 H 0.1178 0.2455 0.3123 0.025 Uiso 1 1 calc R . . C26 C 0.4972(3) 0.20177(11) 0.12111(19) 0.0218(6) Uani 1 1 d . . . C21 C -0.0076(4) 0.38320(11) 0.2884(2) 0.0263(7) Uani 1 1 d . . . H21A H -0.0258 0.3969 0.3420 0.032 Uiso 1 1 calc R . . H21B H -0.0958 0.3823 0.2549 0.032 Uiso 1 1 calc R . . C4 C -0.1312(3) 0.21470(11) -0.04457(19) 0.0204(6) Uani 1 1 d . . . C19 C -0.0275(3) 0.29856(11) 0.33433(19) 0.0221(7) Uani 1 1 d . . . C23 C 0.2311(3) 0.04251(11) 0.15480(19) 0.0199(6) Uani 1 1 d . . . H23A H 0.2253 0.0082 0.1358 0.024 Uiso 1 1 calc R . . H23B H 0.2682 0.0423 0.2116 0.024 Uiso 1 1 calc R . . C30 C 0.4502(3) 0.28863(12) 0.14600(19) 0.0221(6) Uani 1 1 d . . . C24 C 0.3323(3) 0.07152(11) 0.1026(2) 0.0208(6) Uani 1 1 d . . . H24A H 0.4198 0.0529 0.0995 0.025 Uiso 1 1 calc R . . H24B H 0.2903 0.0752 0.0471 0.025 Uiso 1 1 calc R . . C7 C -0.0468(3) 0.30904(11) -0.09685(19) 0.0219(6) Uani 1 1 d . . . H7 H -0.0192 0.3404 -0.1145 0.026 Uiso 1 1 calc R . . C14 C 0.0297(4) 0.16074(11) 0.37360(19) 0.0237(7) Uani 1 1 d . . . H14A H 0.1319 0.1643 0.3760 0.028 Uiso 1 1 calc R . . H14B H 0.0044 0.1433 0.4229 0.028 Uiso 1 1 calc R . . C29 C 0.5813(3) 0.29425(12) 0.1880(2) 0.0256(7) Uani 1 1 d . . . H29 H 0.6096 0.3250 0.2101 0.031 Uiso 1 1 calc R . . C33 C 0.2728(3) 0.40984(11) 0.1373(2) 0.0267(7) Uani 1 1 d . . . H33A H 0.2724 0.4108 0.0777 0.032 Uiso 1 1 calc R . . H33B H 0.2949 0.4432 0.1577 0.032 Uiso 1 1 calc R . . C1 C 0.0110(3) 0.04834(11) 0.07425(19) 0.0205(6) Uani 1 1 d . . . H1A H -0.0268 0.0152 0.0827 0.025 Uiso 1 1 calc R . . H1B H 0.0762 0.0461 0.0305 0.025 Uiso 1 1 calc R . . C3 C -0.1801(3) 0.16432(11) -0.01573(19) 0.0211(6) Uani 1 1 d . . . H3C H -0.2436 0.1691 0.0283 0.025 Uiso 1 1 calc R . . H3D H -0.2326 0.1477 -0.0608 0.025 Uiso 1 1 calc R . . C10 C 0.0047(4) 0.38308(11) 0.0239(2) 0.0244(7) Uani 1 1 d . . . H10A H -0.0671 0.3963 -0.0152 0.029 Uiso 1 1 calc R . . H10B H 0.0949 0.3832 -0.0015 0.029 Uiso 1 1 calc R . . C28 C 0.6697(3) 0.25231(12) 0.1962(2) 0.0231(7) Uani 1 1 d . . . H28 H 0.7583 0.2553 0.2237 0.028 Uiso 1 1 calc R . . C15 C -0.0376(3) 0.21206(11) 0.37158(19) 0.0223(7) Uani 1 1 d . . . C18 C -0.1562(3) 0.30766(12) 0.3683(2) 0.0235(7) Uani 1 1 d . . . H18 H -0.1955 0.3395 0.3672 0.028 Uiso 1 1 calc R . . C9 C -0.1037(3) 0.25274(11) 0.0125(2) 0.0211(6) Uani 1 1 d . . . H9 H -0.1151 0.2470 0.0681 0.025 Uiso 1 1 calc R . . C11 C 0.0128(3) 0.41402(11) 0.1014(2) 0.0234(7) Uani 1 1 d . . . H11A H -0.0777 0.4129 0.1264 0.028 Uiso 1 1 calc R . . H11B H 0.0321 0.4485 0.0876 0.028 Uiso 1 1 calc R . . C22 C 0.1013(4) 0.41427(12) 0.2473(2) 0.0273(7) Uani 1 1 d . . . H22A H 0.0689 0.4486 0.2434 0.033 Uiso 1 1 calc R . . H22B H 0.1894 0.4138 0.2808 0.033 Uiso 1 1 calc R . . C12 C 0.0139(3) 0.04993(11) 0.22311(19) 0.0213(6) Uani 1 1 d . . . H12A H 0.0320 0.0149 0.2351 0.026 Uiso 1 1 calc R . . H12B H -0.0870 0.0538 0.2108 0.026 Uiso 1 1 calc R . . C13 C 0.0576(3) 0.08090(11) 0.2987(2) 0.0224(7) Uani 1 1 d . . . H13A H 0.0367 0.0623 0.3477 0.027 Uiso 1 1 calc R . . H13B H 0.1590 0.0865 0.3002 0.027 Uiso 1 1 calc R . . C5 C -0.1166(3) 0.22411(12) -0.12788(19) 0.0215(6) Uani 1 1 d . . . H5 H -0.1339 0.1988 -0.1664 0.026 Uiso 1 1 calc R . . C27 C 0.6278(3) 0.20693(12) 0.16435(19) 0.0228(7) Uani 1 1 d . . . H27 H 0.6870 0.1793 0.1716 0.027 Uiso 1 1 calc R . . C32 C 0.3866(3) 0.37419(11) 0.1696(2) 0.0261(7) Uani 1 1 d . . . H32A H 0.4788 0.3851 0.1535 0.031 Uiso 1 1 calc R . . H32B H 0.3885 0.3724 0.2292 0.031 Uiso 1 1 calc R . . C16 C -0.1670(3) 0.22048(12) 0.4060(2) 0.0252(7) Uani 1 1 d . . . H16 H -0.2140 0.1943 0.4303 0.030 Uiso 1 1 calc R . . C6 C -0.0767(3) 0.27076(12) -0.1532(2) 0.0237(7) Uani 1 1 d . . . H6 H -0.0695 0.2769 -0.2091 0.028 Uiso 1 1 calc R . . C17 C -0.2250(3) 0.26786(12) 0.4039(2) 0.0247(7) Uani 1 1 d . . . H17 H -0.3116 0.2733 0.4267 0.030 Uiso 1 1 calc R . . C25 C 0.4510(3) 0.15260(11) 0.08405(19) 0.0223(7) Uani 1 1 d . . . H25A H 0.3968 0.1588 0.0326 0.027 Uiso 1 1 calc R . . H25B H 0.5343 0.1336 0.0715 0.027 Uiso 1 1 calc R . . H2W1 H 0.272(5) 0.0299(18) -0.113(3) 0.057(14) Uiso 1 1 d . . . H2W5 H 0.728(4) -0.0345(15) -0.423(2) 0.051(13) Uiso 1 1 d . . . H1W4 H 0.061(2) 0.0556(16) -0.495(3) 0.047(13) Uiso 1 1 d . . . H2W2 H 0.231(4) 0.0315(10) -0.303(3) 0.041(12) Uiso 1 1 d . . . H1W1 H 0.319(5) -0.0131(19) -0.136(3) 0.065(16) Uiso 1 1 d . . . H1W5 H 0.634(5) -0.0442(14) -0.367(3) 0.074(17) Uiso 1 1 d . . . H1W3 H 0.819(4) 0.0595(13) -0.5782(17) 0.034(11) Uiso 1 1 d . . . H1W2 H 0.157(5) 0.0650(17) -0.2684(17) 0.058(14) Uiso 1 1 d . . . H2W3 H 0.848(4) 0.0186(8) -0.532(3) 0.048(13) Uiso 1 1 d . . . H1W6 H 0.512(3) 0.0391(15) -0.063(3) 0.050(13) Uiso 1 1 d . . . H2W6 H 0.605(17) 0.042(5) 0.004(3) 0.055(8) Uiso 1 1 d . . . H2W4 H 0.158(5) 0.0605(17) -0.432(3) 0.058(15) 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 0.0218(4) 0.0190(4) 0.0229(4) -0.0005(3) 0.0024(3) -0.0007(3) Cl2 0.0328(4) 0.0225(4) 0.0235(4) 0.0006(3) 0.0090(3) 0.0032(3) S1 0.0174(4) 0.0192(4) 0.0214(4) 0.0000(3) 0.0026(3) 0.0010(3) O4 0.0165(10) 0.0213(11) 0.0230(12) -0.0006(9) 0.0033(9) 0.0032(8) O5 0.0234(12) 0.0317(13) 0.0253(13) 0.0009(10) 0.0052(10) 0.0022(9) O6 0.0234(12) 0.0334(13) 0.0240(12) 0.0016(10) -0.0015(9) -0.0025(9) O7 0.0254(12) 0.0208(12) 0.0456(15) 0.0025(10) 0.0046(11) 0.0050(9) O1 0.0364(13) 0.0191(11) 0.0217(12) -0.0002(9) 0.0016(10) -0.0042(9) OW5 0.0311(14) 0.0344(13) 0.0284(15) 0.0019(11) 0.0049(12) -0.0019(10) O2 0.0235(12) 0.0197(11) 0.0349(13) 0.0016(9) 0.0054(10) 0.0006(9) O3 0.0255(12) 0.0173(11) 0.0359(13) -0.0016(9) -0.0037(10) -0.0005(9) N5 0.0208(13) 0.0199(13) 0.0174(13) -0.0020(10) 0.0000(10) 0.0009(10) OW3 0.0289(13) 0.0387(15) 0.0270(14) 0.0032(12) -0.0003(11) -0.0008(11) OW2 0.0341(14) 0.0336(14) 0.0241(13) 0.0036(11) 0.0042(11) 0.0127(11) OW1 0.0284(13) 0.0287(14) 0.0287(14) -0.0037(11) -0.0052(11) 0.0029(10) OW6 0.0303(14) 0.0374(15) 0.0254(16) -0.0022(12) -0.0013(12) -0.0041(11) N2 0.0217(13) 0.0202(13) 0.0232(14) -0.0006(11) -0.0008(11) 0.0003(10) N4 0.0214(13) 0.0202(13) 0.0165(13) 0.0011(10) 0.0022(10) -0.0005(10) N3 0.0150(12) 0.0255(14) 0.0183(13) -0.0007(10) 0.0057(10) -0.0001(10) OW4 0.0311(15) 0.0330(15) 0.0237(14) -0.0020(11) 0.0036(11) 0.0038(11) N1 0.0177(12) 0.0148(12) 0.0214(13) -0.0012(10) 0.0030(10) -0.0003(9) C2 0.0211(16) 0.0227(16) 0.0228(16) 0.0007(12) 0.0019(13) -0.0027(12) C31 0.0204(15) 0.0229(16) 0.0197(16) 0.0027(12) 0.0024(12) -0.0047(12) C8 0.0189(15) 0.0208(15) 0.0220(16) -0.0005(12) -0.0006(12) 0.0001(11) C20 0.0188(15) 0.0201(15) 0.0233(16) -0.0049(12) 0.0038(13) 0.0004(11) C26 0.0260(16) 0.0231(16) 0.0170(15) 0.0019(12) 0.0074(12) -0.0009(12) C21 0.0348(19) 0.0207(16) 0.0234(17) -0.0002(13) 0.0033(14) 0.0032(13) C4 0.0167(15) 0.0225(15) 0.0221(16) 0.0028(12) 0.0025(12) 0.0013(11) C19 0.0219(16) 0.0227(16) 0.0213(16) -0.0001(12) -0.0009(13) -0.0025(12) C23 0.0195(15) 0.0211(15) 0.0196(15) 0.0007(12) 0.0042(12) -0.0006(11) C30 0.0241(16) 0.0238(16) 0.0188(15) 0.0036(12) 0.0047(12) 0.0023(12) C24 0.0195(15) 0.0198(15) 0.0232(16) -0.0047(12) 0.0017(12) -0.0025(11) C7 0.0231(16) 0.0205(15) 0.0224(16) 0.0046(12) 0.0024(13) 0.0005(12) C14 0.0289(17) 0.0241(16) 0.0180(16) 0.0003(12) 0.0016(13) 0.0025(13) C29 0.0251(17) 0.0252(17) 0.0264(17) -0.0029(13) 0.0012(13) -0.0030(13) C33 0.0241(17) 0.0190(16) 0.037(2) 0.0032(14) 0.0041(14) -0.0045(12) C1 0.0230(16) 0.0202(15) 0.0186(15) -0.0045(12) 0.0036(12) -0.0010(12) C3 0.0150(14) 0.0252(16) 0.0228(16) -0.0009(12) 0.0003(12) 0.0005(12) C10 0.0313(18) 0.0151(14) 0.0265(17) 0.0044(12) -0.0011(14) -0.0007(12) C28 0.0214(16) 0.0274(17) 0.0205(16) -0.0009(12) 0.0006(13) -0.0012(12) C15 0.0248(16) 0.0208(15) 0.0210(16) -0.0035(12) -0.0015(13) 0.0008(12) C18 0.0227(16) 0.0235(16) 0.0240(17) -0.0039(13) -0.0015(13) 0.0027(12) C9 0.0204(15) 0.0231(16) 0.0199(15) 0.0031(12) 0.0013(12) -0.0002(12) C11 0.0242(16) 0.0173(15) 0.0287(18) 0.0016(12) 0.0013(13) 0.0018(12) C22 0.0345(19) 0.0187(16) 0.0284(18) -0.0056(13) -0.0002(15) 0.0009(13) C12 0.0215(16) 0.0231(15) 0.0199(15) 0.0017(12) 0.0057(12) 0.0010(12) C13 0.0219(16) 0.0210(15) 0.0245(17) 0.0026(12) 0.0030(13) 0.0060(12) C5 0.0205(15) 0.0248(16) 0.0192(15) -0.0034(12) 0.0021(12) 0.0000(12) C27 0.0229(16) 0.0258(16) 0.0203(16) 0.0044(12) 0.0079(13) 0.0059(12) C32 0.0227(16) 0.0203(16) 0.0348(19) 0.0020(14) -0.0016(14) -0.0038(12) C16 0.0263(17) 0.0265(17) 0.0229(17) 0.0014(13) 0.0016(13) -0.0030(13) C6 0.0252(16) 0.0266(17) 0.0197(16) 0.0034(13) 0.0054(13) 0.0037(13) C17 0.0202(16) 0.0292(17) 0.0248(17) -0.0044(13) 0.0031(13) 0.0000(12) C25 0.0256(16) 0.0217(16) 0.0204(16) 0.0012(12) 0.0062(13) -0.0008(12) _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 O7 1.466(2) . ? S1 O5 1.469(2) . ? S1 O6 1.480(2) . ? S1 O4 1.481(2) . ? O1 C8 1.378(4) . ? O1 C10 1.427(4) . ? OW5 H2W5 0.85(4) . ? OW5 H1W5 0.84(4) . ? O2 C19 1.390(4) . ? O2 C21 1.418(4) . ? O3 C30 1.392(4) . ? O3 C32 1.420(4) . ? N5 C25 1.494(4) . ? N5 C24 1.495(4) . ? N5 H5A 0.9000 . ? N5 H5B 0.9000 . ? OW3 H1W3 0.846(18) . ? OW3 H2W3 0.862(19) . ? OW2 H2W2 0.832(19) . ? OW2 H1W2 0.858(19) . ? OW1 H2W1 0.83(5) . ? OW1 H1W1 0.84(6) . ? OW6 H1W6 0.851(19) . ? OW6 H2W6 0.84(6) . ? N2 C22 1.505(4) . ? N2 C33 1.510(4) . ? N2 C11 1.514(4) . ? N4 C13 1.493(4) . ? N4 C14 1.502(4) . ? N4 H4A 0.9000 . ? N4 H4B 0.9000 . ? N3 C2 1.491(4) . ? N3 C3 1.505(4) . ? N3 H3A 0.9000 . ? N3 H3B 0.9000 . ? OW4 H1W4 0.848(19) . ? OW4 H2W4 0.85(5) . ? N1 C23 1.456(4) . ? N1 C12 1.472(4) . ? N1 C1 1.473(4) . ? N1 H1 0.9100 . ? C2 C1 1.513(4) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C31 C30 1.384(4) . ? C31 C26 1.394(4) . ? C31 H31 0.9300 . ? C8 C7 1.387(4) . ? C8 C9 1.390(4) . ? C20 C15 1.380(4) . ? C20 C19 1.389(4) . ? C20 H20 0.9300 . ? C26 C27 1.393(5) . ? C26 C25 1.502(4) . ? C21 C22 1.510(5) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C4 C9 1.392(4) . ? C4 C5 1.394(4) . ? C4 C3 1.509(4) . ? C19 C18 1.388(5) . ? C23 C24 1.528(4) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C30 C29 1.390(4) . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C7 C6 1.393(4) . ? C7 H7 0.9300 . ? C14 C15 1.513(4) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C29 C28 1.402(4) . ? C29 H29 0.9300 . ? C33 C32 1.510(4) . ? C33 H33A 0.9700 . ? C33 H33B 0.9700 . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C3 H3C 0.9700 . ? C3 H3D 0.9700 . ? C10 C11 1.507(4) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C28 C27 1.370(4) . ? C28 H28 0.9300 . ? C15 C16 1.395(5) . ? C18 C17 1.392(5) . ? C18 H18 0.9300 . ? C9 H9 0.9300 . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C12 C13 1.520(4) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C5 C6 1.374(4) . ? C5 H5 0.9300 . ? C27 H27 0.9300 . ? C32 H32A 0.9700 . ? C32 H32B 0.9700 . ? C16 C17 1.381(4) . ? C16 H16 0.9300 . ? C6 H6 0.9300 . ? C17 H17 0.9300 . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? 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 O7 S1 O5 110.26(14) . . ? O7 S1 O6 110.15(14) . . ? O5 S1 O6 109.31(13) . . ? O7 S1 O4 109.06(13) . . ? O5 S1 O4 108.91(13) . . ? O6 S1 O4 109.12(13) . . ? C8 O1 C10 117.1(2) . . ? H2W5 OW5 H1W5 104(4) . . ? C19 O2 C21 117.1(2) . . ? C30 O3 C32 117.5(2) . . ? C25 N5 C24 111.4(2) . . ? C25 N5 H5A 109.3 . . ? C24 N5 H5A 109.3 . . ? C25 N5 H5B 109.3 . . ? C24 N5 H5B 109.3 . . ? H5A N5 H5B 108.0 . . ? H1W3 OW3 H2W3 104(4) . . ? H2W2 OW2 H1W2 99(4) . . ? H2W1 OW1 H1W1 101(4) . . ? H1W6 OW6 H2W6 107(10) . . ? C22 N2 C33 111.2(2) . . ? C22 N2 C11 109.8(2) . . ? C33 N2 C11 111.4(2) . . ? C13 N4 C14 111.8(2) . . ? C13 N4 H4A 109.2 . . ? C14 N4 H4A 109.2 . . ? C13 N4 H4B 109.2 . . ? C14 N4 H4B 109.2 . . ? H4A N4 H4B 107.9 . . ? C2 N3 C3 111.9(2) . . ? C2 N3 H3A 109.2 . . ? C3 N3 H3A 109.2 . . ? C2 N3 H3B 109.2 . . ? C3 N3 H3B 109.2 . . ? H3A N3 H3B 107.9 . . ? H1W4 OW4 H2W4 104(4) . . ? C23 N1 C12 110.2(2) . . ? C23 N1 C1 110.1(2) . . ? C12 N1 C1 110.6(2) . . ? C23 N1 H1 108.6 . . ? C12 N1 H1 108.6 . . ? C1 N1 H1 108.6 . . ? N3 C2 C1 112.6(2) . . ? N3 C2 H2A 109.1 . . ? C1 C2 H2A 109.1 . . ? N3 C2 H2B 109.1 . . ? C1 C2 H2B 109.1 . . ? H2A C2 H2B 107.8 . . ? C30 C31 C26 120.0(3) . . ? C30 C31 H31 120.0 . . ? C26 C31 H31 120.0 . . ? O1 C8 C7 124.2(3) . . ? O1 C8 C9 114.9(3) . . ? C7 C8 C9 120.9(3) . . ? C15 C20 C19 119.8(3) . . ? C15 C20 H20 120.1 . . ? C19 C20 H20 120.1 . . ? C27 C26 C31 119.1(3) . . ? C27 C26 C25 121.2(3) . . ? C31 C26 C25 119.6(3) . . ? O2 C21 C22 105.5(3) . . ? O2 C21 H21A 110.6 . . ? C22 C21 H21A 110.6 . . ? O2 C21 H21B 110.6 . . ? C22 C21 H21B 110.6 . . ? H21A C21 H21B 108.8 . . ? C9 C4 C5 119.4(3) . . ? C9 C4 C3 119.6(3) . . ? C5 C4 C3 120.9(3) . . ? C18 C19 C20 121.2(3) . . ? C18 C19 O2 124.3(3) . . ? C20 C19 O2 114.5(3) . . ? N1 C23 C24 111.8(2) . . ? N1 C23 H23A 109.3 . . ? C24 C23 H23A 109.3 . . ? N1 C23 H23B 109.3 . . ? C24 C23 H23B 109.3 . . ? H23A C23 H23B 107.9 . . ? C31 C30 C29 121.2(3) . . ? C31 C30 O3 114.7(3) . . ? C29 C30 O3 124.1(3) . . ? N5 C24 C23 110.9(2) . . ? N5 C24 H24A 109.5 . . ? C23 C24 H24A 109.5 . . ? N5 C24 H24B 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 108.0 . . ? C8 C7 C6 118.5(3) . . ? C8 C7 H7 120.8 . . ? C6 C7 H7 120.8 . . ? N4 C14 C15 112.0(2) . . ? N4 C14 H14A 109.2 . . ? C15 C14 H14A 109.2 . . ? N4 C14 H14B 109.2 . . ? C15 C14 H14B 109.2 . . ? H14A C14 H14B 107.9 . . ? C30 C29 C28 118.1(3) . . ? C30 C29 H29 120.9 . . ? C28 C29 H29 120.9 . . ? C32 C33 N2 112.6(3) . . ? C32 C33 H33A 109.1 . . ? N2 C33 H33A 109.1 . . ? C32 C33 H33B 109.1 . . ? N2 C33 H33B 109.1 . . ? H33A C33 H33B 107.8 . . ? N1 C1 C2 114.0(2) . . ? N1 C1 H1A 108.8 . . ? C2 C1 H1A 108.8 . . ? N1 C1 H1B 108.8 . . ? C2 C1 H1B 108.8 . . ? H1A C1 H1B 107.6 . . ? N3 C3 C4 112.6(2) . . ? N3 C3 H3C 109.1 . . ? C4 C3 H3C 109.1 . . ? N3 C3 H3D 109.1 . . ? C4 C3 H3D 109.1 . . ? H3C C3 H3D 107.8 . . ? O1 C10 C11 106.3(3) . . ? O1 C10 H10A 110.5 . . ? C11 C10 H10A 110.5 . . ? O1 C10 H10B 110.5 . . ? C11 C10 H10B 110.5 . . ? H10A C10 H10B 108.7 . . ? C27 C28 C29 121.0(3) . . ? C27 C28 H28 119.5 . . ? C29 C28 H28 119.5 . . ? C20 C15 C16 119.9(3) . . ? C20 C15 C14 119.0(3) . . ? C16 C15 C14 121.1(3) . . ? C19 C18 C17 118.3(3) . . ? C19 C18 H18 120.9 . . ? C17 C18 H18 120.9 . . ? C8 C9 C4 119.8(3) . . ? C8 C9 H9 120.1 . . ? C4 C9 H9 120.1 . . ? C10 C11 N2 111.5(2) . . ? C10 C11 H11A 109.3 . . ? N2 C11 H11A 109.3 . . ? C10 C11 H11B 109.3 . . ? N2 C11 H11B 109.3 . . ? H11A C11 H11B 108.0 . . ? N2 C22 C21 111.8(3) . . ? N2 C22 H22A 109.2 . . ? C21 C22 H22A 109.2 . . ? N2 C22 H22B 109.2 . . ? C21 C22 H22B 109.2 . . ? H22A C22 H22B 107.9 . . ? N1 C12 C13 112.6(2) . . ? N1 C12 H12A 109.1 . . ? C13 C12 H12A 109.1 . . ? N1 C12 H12B 109.1 . . ? C13 C12 H12B 109.1 . . ? H12A C12 H12B 107.8 . . ? N4 C13 C12 112.4(2) . . ? N4 C13 H13A 109.1 . . ? C12 C13 H13A 109.1 . . ? N4 C13 H13B 109.1 . . ? C12 C13 H13B 109.1 . . ? H13A C13 H13B 107.8 . . ? C6 C5 C4 120.0(3) . . ? C6 C5 H5 120.0 . . ? C4 C5 H5 120.0 . . ? C28 C27 C26 120.5(3) . . ? C28 C27 H27 119.7 . . ? C26 C27 H27 119.7 . . ? O3 C32 C33 106.0(3) . . ? O3 C32 H32A 110.5 . . ? C33 C32 H32A 110.5 . . ? O3 C32 H32B 110.5 . . ? C33 C32 H32B 110.5 . . ? H32A C32 H32B 108.7 . . ? C17 C16 C15 119.7(3) . . ? C17 C16 H16 120.2 . . ? C15 C16 H16 120.2 . . ? C5 C6 C7 121.3(3) . . ? C5 C6 H6 119.4 . . ? C7 C6 H6 119.4 . . ? C16 C17 C18 121.2(3) . . ? C16 C17 H17 119.4 . . ? C18 C17 H17 119.4 . . ? N5 C25 C26 113.6(2) . . ? N5 C25 H25A 108.9 . . ? C26 C25 H25A 108.9 . . ? N5 C25 H25B 108.9 . . ? C26 C25 H25B 108.9 . . ? H25A C25 H25B 107.7 . . ? 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 C3 N3 C2 C1 177.5(2) . . . . ? C10 O1 C8 C7 3.8(4) . . . . ? C10 O1 C8 C9 -175.3(3) . . . . ? C30 C31 C26 C27 -0.6(5) . . . . ? C30 C31 C26 C25 179.8(3) . . . . ? C19 O2 C21 C22 178.9(2) . . . . ? C15 C20 C19 C18 -0.4(5) . . . . ? C15 C20 C19 O2 -179.9(3) . . . . ? C21 O2 C19 C18 -3.5(4) . . . . ? C21 O2 C19 C20 176.0(3) . . . . ? C12 N1 C23 C24 -157.2(2) . . . . ? C1 N1 C23 C24 80.6(3) . . . . ? C26 C31 C30 C29 1.7(5) . . . . ? C26 C31 C30 O3 -178.6(3) . . . . ? C32 O3 C30 C31 178.5(3) . . . . ? C32 O3 C30 C29 -1.8(5) . . . . ? C25 N5 C24 C23 -174.5(2) . . . . ? N1 C23 C24 N5 68.6(3) . . . . ? O1 C8 C7 C6 179.2(3) . . . . ? C9 C8 C7 C6 -1.6(4) . . . . ? C13 N4 C14 C15 176.1(3) . . . . ? C31 C30 C29 C28 -1.1(5) . . . . ? O3 C30 C29 C28 179.2(3) . . . . ? C22 N2 C33 C32 83.9(3) . . . . ? C11 N2 C33 C32 -153.3(3) . . . . ? C23 N1 C1 C2 -157.6(2) . . . . ? C12 N1 C1 C2 80.5(3) . . . . ? N3 C2 C1 N1 71.2(3) . . . . ? C2 N3 C3 C4 177.1(3) . . . . ? C9 C4 C3 N3 -83.6(3) . . . . ? C5 C4 C3 N3 98.1(3) . . . . ? C8 O1 C10 C11 173.5(2) . . . . ? C30 C29 C28 C27 -0.6(5) . . . . ? C19 C20 C15 C16 0.3(5) . . . . ? C19 C20 C15 C14 -179.0(3) . . . . ? N4 C14 C15 C20 -90.9(3) . . . . ? N4 C14 C15 C16 89.7(4) . . . . ? C20 C19 C18 C17 0.1(5) . . . . ? O2 C19 C18 C17 179.5(3) . . . . ? O1 C8 C9 C4 -178.2(3) . . . . ? C7 C8 C9 C4 2.6(5) . . . . ? C5 C4 C9 C8 -1.4(4) . . . . ? C3 C4 C9 C8 -179.8(3) . . . . ? O1 C10 C11 N2 61.9(3) . . . . ? C22 N2 C11 C10 -160.7(3) . . . . ? C33 N2 C11 C10 75.6(3) . . . . ? C33 N2 C22 C21 -155.0(3) . . . . ? C11 N2 C22 C21 81.2(3) . . . . ? O2 C21 C22 N2 62.6(3) . . . . ? C23 N1 C12 C13 79.4(3) . . . . ? C1 N1 C12 C13 -158.6(2) . . . . ? C14 N4 C13 C12 -178.9(3) . . . . ? N1 C12 C13 N4 81.9(3) . . . . ? C9 C4 C5 C6 -0.6(4) . . . . ? C3 C4 C5 C6 177.7(3) . . . . ? C29 C28 C27 C26 1.6(5) . . . . ? C31 C26 C27 C28 -1.0(5) . . . . ? C25 C26 C27 C28 178.5(3) . . . . ? C30 O3 C32 C33 172.0(3) . . . . ? N2 C33 C32 O3 61.5(4) . . . . ? C20 C15 C16 C17 0.0(5) . . . . ? C14 C15 C16 C17 179.4(3) . . . . ? C4 C5 C6 C7 1.6(5) . . . . ? C8 C7 C6 C5 -0.4(5) . . . . ? C15 C16 C17 C18 -0.3(5) . . . . ? C19 C18 C17 C16 0.3(5) . . . . ? C24 N5 C25 C26 -174.4(3) . . . . ? C27 C26 C25 N5 93.9(4) . . . . ? C31 C26 C25 N5 -86.6(3) . . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 28.35 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.678 _refine_diff_density_min -0.428 _refine_diff_density_rms 0.130 data_Complex5 #TrackingRef 'B924157D_ccdc_754955_754960_cif.txt' _database_code_depnum_ccdc_archive 'CCDC 754959' #TrackingRef 'Complex1-6.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C33 H51 Cl N8 O13' _chemical_formula_sum 'C33 H51 Cl N8 O13' _chemical_formula_weight 803.27 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 Monoclinic _symmetry_space_group_name_H-M 'P 21/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 9.389(2) _cell_length_b 24.772(4) _cell_length_c 16.532(3) _cell_angle_alpha 90.00 _cell_angle_beta 97.961(4) _cell_angle_gamma 90.00 _cell_volume 3808.0(12) _cell_formula_units_Z 4 _cell_measurement_temperature 100(1) _cell_measurement_reflns_used ? _cell_measurement_theta_min 2.0 _cell_measurement_theta_max 28.3 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.401 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1704 _exptl_absorpt_coefficient_mu 0.175 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9691 _exptl_absorpt_correction_T_max 0.9742 _exptl_absorpt_process_details 'SADABS 2.10 (Bruker 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(1) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX' _diffrn_measurement_method /w-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 24621 _diffrn_reflns_av_R_equivalents 0.0610 _diffrn_reflns_av_sigmaI/netI 0.0823 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -33 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 28.40 _reflns_number_total 9396 _reflns_number_gt 5431 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART 5.628 (Bruker, 2003)' _computing_cell_refinement 'SAINT 6.45 ( Bruker, 2003)' _computing_data_reduction 'SAINT 6.45 (Bruker, 2003)' _computing_structure_solution SIR-97 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Diamond 2.1e' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0400P)^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 9396 _refine_ls_number_parameters 439 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1006 _refine_ls_R_factor_gt 0.0754 _refine_ls_wR_factor_ref 0.2233 _refine_ls_wR_factor_gt 0.1757 _refine_ls_goodness_of_fit_ref 1.112 _refine_ls_restrained_S_all 1.112 _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 Cl1 Cl 0.27057(18) 0.30599(7) 0.40446(10) 0.0416(5) Uani 1 1 d . . . O7 O 0.1202(6) 0.4460(5) 0.1076(5) 0.0355(18) Uani 1 1 d . . . O2 O 0.1278(3) 0.15856(17) 0.2862(2) 0.0362(10) Uani 1 1 d . . . O1 O 0.2508(4) 0.15011(16) 0.5307(2) 0.0324(10) Uani 1 1 d . . . O3 O 0.5243(3) 0.15717(17) 0.3676(3) 0.0349(11) Uani 1 1 d . . . O4 O -0.0937(3) 0.40047(19) 0.5973(3) 0.0372(12) Uani 1 1 d . . . O5 O -0.1380(2) 0.4067(2) 0.4666(3) 0.0406(13) Uani 1 1 d . . . O6 O -0.3139(3) 0.40880(18) 0.5394(3) 0.0329(11) Uani 1 1 d . . . N2 N 0.2650(3) 0.4434(2) 0.4049(3) 0.0312(11) Uani 1 1 d . . . H2 H 0.2661 0.4068 0.4001 0.037 Uiso 1 1 calc R . . N4 N 0.0974(2) 0.3786(2) 0.2678(3) 0.0343(12) Uani 1 1 d . . . H4A H 0.1546 0.3873 0.2304 0.041 Uiso 1 1 calc R . . H4B H 0.1509 0.3598 0.3075 0.041 Uiso 1 1 calc R . . N3 N 0.1838(2) 0.36964(19) 0.5516(3) 0.0297(11) Uani 1 1 d . . . H3A H 0.1938 0.3518 0.5054 0.036 Uiso 1 1 calc R . . H3B H 0.0897 0.3766 0.5511 0.036 Uiso 1 1 calc R . . N5 N 0.5403(3) 0.3781(2) 0.3838(3) 0.0341(12) Uani 1 1 d . . . H5A H 0.5946 0.3815 0.4328 0.041 Uiso 1 1 calc R . . H5B H 0.4603 0.3598 0.3910 0.041 Uiso 1 1 calc R . . N7 N 0.2397(3) 0.4258(2) 0.1115(3) 0.0333(12) Uani 1 1 d . . . C7 C 0.1657(2) 0.2789(2) 0.6149(3) 0.0288(13) Uani 1 1 d . . . N1 N 0.3050(2) 0.0871(2) 0.3937(3) 0.0367(12) Uani 1 1 d . . . C25 C 0.6235(3) 0.1980(2) 0.3826(4) 0.0314(13) Uani 1 1 d . . . C26 C 0.7617(3) 0.1911(2) 0.4223(4) 0.0315(13) Uani 1 1 d . . . H26 H 0.7925 0.1574 0.4425 0.038 Uiso 1 1 calc R . . C8 C 0.2330(2) 0.2393(2) 0.5764(4) 0.0312(13) Uani 1 1 d . . . H8 H 0.3168 0.2470 0.5546 0.037 Uiso 1 1 calc R . . C9 C 0.2344(2) 0.3343(2) 0.6232(4) 0.0323(13) Uani 1 1 d . . . H9A H 0.2116 0.3513 0.6726 0.039 Uiso 1 1 calc R . . H9B H 0.3381 0.3304 0.6281 0.039 Uiso 1 1 calc R . . N8 N 0.7487(3) 0.5199(2) 0.2373(3) 0.0354(13) Uani 1 1 d . . . C18 C 0.0405(3) 0.2919(3) 0.2007(4) 0.0347(14) Uani 1 1 d . . . C11 C 0.2074(4) 0.4571(2) 0.4805(4) 0.0318(13) Uani 1 1 d . . . H11A H 0.1033 0.4545 0.4705 0.038 Uiso 1 1 calc R . . H11B H 0.2318 0.4942 0.4946 0.038 Uiso 1 1 calc R . . N6 N -0.1797(2) 0.4047(2) 0.5349(4) 0.0305(13) Uani 1 1 d . . . O10 O 0.6294(3) 0.5325(2) 0.2548(3) 0.0352(15) Uani 1 1 d . . . C3 C 0.1754(4) 0.1877(2) 0.5703(3) 0.0292(13) Uani 1 1 d . . . C29 C 0.6692(4) 0.2925(2) 0.3635(4) 0.0328(13) Uani 1 1 d . . . C19 C 0.0556(3) 0.2471(2) 0.2531(4) 0.0322(13) Uani 1 1 d . . . H19 H 0.0271 0.2496 0.3046 0.039 Uiso 1 1 calc R . . C21 C 0.0494(3) 0.4290(2) 0.3035(4) 0.0309(13) Uani 1 1 d . . . H21A H -0.0013 0.4202 0.3491 0.037 Uiso 1 1 calc R . . H21B H -0.0171 0.4477 0.2628 0.037 Uiso 1 1 calc R . . C28 C 0.8081(4) 0.2852(3) 0.4033(4) 0.0338(13) Uani 1 1 d . . . H28 H 0.8704 0.3146 0.4108 0.041 Uiso 1 1 calc R . . C14 C 0.1124(4) 0.1991(2) 0.2288(4) 0.0313(13) Uani 1 1 d . . . C2 C 0.1928(3) 0.0973(2) 0.5223(4) 0.0368(14) Uani 1 1 d . . . H2A H 0.0976 0.0977 0.4909 0.044 Uiso 1 1 calc R . . H2B H 0.1864 0.0815 0.5754 0.044 Uiso 1 1 calc R . . C4 C 0.0513(3) 0.1761(2) 0.6034(4) 0.0316(13) Uani 1 1 d . . . H4 H 0.0134 0.1413 0.6004 0.038 Uiso 1 1 calc R . . C32 C 0.4992(2) 0.4329(2) 0.3509(4) 0.0326(14) Uani 1 1 d . . . H32A H 0.4419 0.4294 0.2977 0.043 Uiso 1 1 calc R . . H32B H 0.5854 0.4530 0.3441 0.043 Uiso 1 1 calc R . . O12 O 0.8586(3) 0.5430(3) 0.2740(4) 0.0364(12) Uani 1 1 d . . . C6 C 0.0397(3) 0.2682(3) 0.6473(4) 0.0335(14) Uani 1 1 d . . . H6 H -0.0062 0.2953 0.6727 0.040 Uiso 1 1 calc R . . C13 C 0.1557(3) 0.1062(3) 0.2597(4) 0.0367(14) Uani 1 1 d . . . H13A H 0.2421 0.1060 0.2336 0.044 Uiso 1 1 calc R . . H13B H 0.0761 0.0935 0.2207 0.044 Uiso 1 1 calc R . . C22 C 0.1733(3) 0.4657(3) 0.3326(4) 0.0360(14) Uani 1 1 d . . . H22A H 0.2310 0.4709 0.2889 0.043 Uiso 1 1 calc R . . H22B H 0.1366 0.5006 0.3463 0.043 Uiso 1 1 calc R . . C27 C 0.8546(3) 0.2353(3) 0.4317(4) 0.0341(14) Uani 1 1 d . . . H27 H 0.9485 0.2309 0.4574 0.041 Uiso 1 1 calc R . . C30 C 0.5780(2) 0.2484(2) 0.3527(3) 0.0296(13) Uani 1 1 d . . . H30 H 0.4853 0.2526 0.3251 0.036 Uiso 1 1 calc R . . O9 O 0.3039(5) 0.4308(4) 0.0494(5) 0.0361(13) Uani 1 1 d . . . C5 C -0.0156(3) 0.2170(3) 0.6410(4) 0.0336(14) Uani 1 1 d . . . H5 H -0.0999 0.2095 0.6624 0.040 Uiso 1 1 calc R . . C16 C 0.1324(7) 0.2388(3) 0.0978(4) 0.0363(13) Uani 1 1 d . . . H16 H 0.1571 0.2359 0.0454 0.044 Uiso 1 1 calc R . . C20 C -0.0177(3) 0.3435(3) 0.2289(4) 0.0336(14) Uani 1 1 d . . . H20A H -0.0708 0.3621 0.1826 0.040 Uiso 1 1 calc R . . H20B H -0.0839 0.3357 0.2675 0.040 Uiso 1 1 calc R . . C1 C 0.2976(3) 0.0654(3) 0.4777(4) 0.0379(13) Uani 1 1 d . . . H1A H 0.3927 0.0667 0.5092 0.050 Uiso 1 1 calc R . . H1B H 0.2676 0.0279 0.4735 0.050 Uiso 1 1 calc R . . C24 C 0.5653(4) 0.1054(2) 0.3957(4) 0.0411(12) Uani 1 1 d . . . H24A H 0.5818 0.1045 0.4549 0.049 Uiso 1 1 calc R . . H24B H 0.6529 0.0943 0.3753 0.049 Uiso 1 1 calc R . . C12 C 0.1751(3) 0.0705(3) 0.3343(4) 0.0404(12) Uani 1 1 d . . . H12A H 0.1865 0.0333 0.3177 0.048 Uiso 1 1 calc R . . H12B H 0.0898 0.0725 0.3612 0.048 Uiso 1 1 calc R . . C33 C 0.4150(3) 0.4636(2) 0.4065(4) 0.0352(14) Uani 1 1 d . . . H33A H 0.4645 0.4613 0.4619 0.042 Uiso 1 1 calc R . . H33B H 0.4118 0.5014 0.3908 0.042 Uiso 1 1 calc R . . O8 O 0.3028(4) 0.4019(4) 0.1726(3) 0.0367(13) Uani 1 1 d . . . O11 O 0.7633(5) 0.4907(4) 0.1780(4) 0.0342(12) Uani 1 1 d . . . C17 C 0.0805(3) 0.2861(3) 0.1229(4) 0.0362(14) Uani 1 1 d . . . H17 H 0.0713 0.3154 0.0874 0.043 Uiso 1 1 calc R . . C15 C 0.1495(7) 0.1932(3) 0.1519(4) 0.0383(15) Uani 1 1 d . . . H15 H 0.1846 0.1605 0.1353 0.046 Uiso 1 1 calc R . . C10 C 0.2628(2) 0.4212(2) 0.5526(4) 0.0327(13) Uani 1 1 d . . . H10A H 0.3640 0.4138 0.5517 0.039 Uiso 1 1 calc R . . H10B H 0.2538 0.4402 0.6029 0.039 Uiso 1 1 calc R . . C23 C 0.4428(3) 0.0688(3) 0.3636(5) 0.0395(13) Uani 1 1 d . . . H23A H 0.4650 0.0321 0.3816 0.051 Uiso 1 1 calc R . . H23B H 0.4299 0.0692 0.3043 0.051 Uiso 1 1 calc R . . C31 C 0.6216(5) 0.3468(3) 0.3283(4) 0.033(5) Uani 1 1 d . . . H31A H 0.7055 0.3673 0.3184 0.048 Uiso 1 1 calc R . . H31B H 0.5614 0.3416 0.2763 0.048 Uiso 1 1 calc R . . OW1 O 0.445(2) 0.4580(3) -0.0713(3) 0.033(4) 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 Cl1 0.0451(10) 0.0379(9) 0.0411(9) -0.0017(7) 0.0029(7) 0.0002(7) O7 0.044(4) 0.037(4) 0.026(4) -0.008(3) 0.004(2) -0.002(3) O2 0.048(3) 0.029(2) 0.031(2) -0.0056(19) 0.0044(19) -0.0001(19) O1 0.042(2) 0.018(2) 0.036(2) -0.0016(17) 0.0005(18) 0.0005(17) O3 0.043(3) 0.021(2) 0.037(3) -0.0050(19) -0.002(2) 0.0022(18) O4 0.046(3) 0.031(3) 0.033(3) 0.000(2) 0.001(2) 0.002(2) O5 0.050(3) 0.041(3) 0.032(3) -0.006(2) 0.007(3) -0.002(2) O6 0.044(2) 0.032(2) 0.022(3) 0.009(2) 0.004(2) 0.001(2) N2 0.037(3) 0.021(2) 0.035(3) 0.001(2) 0.002(2) 0.004(2) N4 0.035(3) 0.029(3) 0.039(3) 0.001(2) 0.007(2) -0.004(2) N3 0.035(3) 0.019(2) 0.033(3) -0.003(2) -0.005(2) 0.0014(19) N5 0.048(3) 0.021(3) 0.034(3) -0.007(2) 0.010(2) 0.000(2) N7 0.045(3) 0.038(3) 0.019(3) -0.002(2) 0.005(2) -0.002(2) C7 0.038(3) 0.021(3) 0.024(3) 0.008(2) -0.005(2) 0.002(2) N1 0.043(3) 0.028(3) 0.037(3) -0.008(2) -0.004(2) 0.002(2) C25 0.043(3) 0.025(3) 0.027(3) -0.003(2) 0.006(2) 0.002(2) C26 0.049(4) 0.021(3) 0.024(3) -0.002(2) 0.007(2) 0.004(3) C8 0.032(3) 0.029(3) 0.031(3) 0.001(3) 0.001(2) -0.002(2) C9 0.040(3) 0.021(3) 0.034(3) -0.001(3) -0.002(2) 0.003(2) N8 0.0473(4) 0.032(4) 0.022(4) -0.006(3) -0.008(3) 0.000(3) C18 0.024(3) 0.046(4) 0.033(3) 0.000(3) -0.002(2) -0.003(3) C11 0.038(3) 0.022(3) 0.035(3) -0.003(3) 0.004(2) 0.001(2) N6 0.043(3) 0.016(2) 0.033(4) 0.004(2) 0.007(3) 0.001(2) O10 0.041(5) 0.035(5) 0.029(5) -0.006(4) 0.007(4) -0.002(4) C3 0.038(3) 0.022(3) 0.026(3) 0.002(2) -0.001(2) 0.004(2) C29 0.050(4) 0.026(3) 0.023(3) -0.002(2) 0.008(3) 0.003(3) C19 0.037(3) 0.030(3) 0.030(3) -0.006(3) 0.005(2) -0.002(2) C21 0.033(3) 0.032(3) 0.027(3) 0.000(3) 0.004(2) 0.003(2) C28 0.043(3) 0.029(3) 0.029(3) -0.004(3) 0.005(3) -0.002(3) C14 0.031(3) 0.031(3) 0.032(3) -0.005(3) 0.004(2) -0.002(2) C2 0.046(4) 0.021(3) 0.040(4) -0.002(3) -0.005(3) -0.003(3) C4 0.034(3) 0.027(3) 0.032(3) 0.006(3) -0.002(2) -0.002(2) C32 0.031(3) 0.027(3) 0.038(4) 0.005(3) 0.001(3) 0.001(2) O12 0.045(4) 0.035(4) 0.027(4) -0.005(3) 0.005(2) -0.002(3) C6 0.039(3) 0.038(4) 0.023(3) 0.006(3) 0.003(2) 0.001(3) C13 0.045(4) 0.032(3) 0.033(3) -0.008(3) 0.005(3) -0.003(3) C22 0.040(3) 0.033(3) 0.035(3) -0.001(3) 0.004(3) 0.003(3) C27 0.043(3) 0.036(4) 0.022(3) 0.000(3) 0.002(2) 0.002(3) C30 0.040(3) 0.025(3) 0.023(3) -0.001(2) 0.003(2) 0.003(2) O9 0.050(4) 0.026(4) 0.032(4) -0.004(3) 0.008(3) 0.002(3) C5 0.036(3) 0.035(3) 0.030(3) 0.010(3) 0.003(2) 0.001(3) C16 0.044(4) 0.036(3) 0.030(3) -0.004(3) 0.011(3) -0.002(3) C20 0.034(3) 0.036(4) 0.030(3) 0.003(3) 0.000(2) -0.003(3) C1 0.053(4) 0.023(3) 0.037(4) -0.003(3) -0.002(3) 0.004(3) C24 0.057(4) 0.021(3) 0.044(4) -0.006(3) 0.003(3) 0.002(3) C12 0.044(4) 0.035(4) 0.040(4) -0.006(3) 0.000(3) -0.003(3) C33 0.045(4) 0.019(3) 0.040(3) 0.002(3) 0.003(3) -0.001(2) O8 0.049(5) 0.035(4) 0.027(5) -0.010(4) 0.004(4) -0.001(4) O11 0.041(4) 0.035(4) 0.025(4) -0.008(3) 0.003(2) -0.002(3) C17 0.035(3) 0.039(4) 0.034(3) 0.001(3) 0.006(3) -0.007(3) C15 0.036(3) 0.043(4) 0.035(3) -0.010(3) 0.005(3) -0.006(3) C10 0.039(3) 0.023(3) 0.035(3) -0.004(3) -0.001(2) -0.001(2) C23 0.047(4) 0.028(3) 0.043(4) -0.012(3) 0.009(3) 0.001(3) C31 0.043(4) 0.029(3) 0.029(3) 0.001(3) 0.010(3) 0.003(3) OW1 0.044(4) 0.033(10) 0.023(4) 0.009(5) 0.006(3) 0.002(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O7 N7 1.223(5) . ? O2 C14 1.375(7) . ? O2 C13 1.406(7) . ? O1 C3 1.388(7) . ? O1 C2 1.417(7) . ? O3 C25 1.373(7) . ? O3 C24 1.401(7) . ? O4 N6 1.223(7) . ? O5 N6 1.246(7) . ? O6 N6 1.276(7) . ? N2 C11 1.468(8) . ? N2 C22 1.479(8) . ? N2 C33 1.492(8) . ? N2 H2 0.9100 . ? N4 C20 1.465(8) . ? N4 C21 1.478(8) . ? N4 H4A 0.9000 . ? N4 H4B 0.9000 . ? N3 C10 1.475(7) . ? N3 C9 1.496(8) . ? N3 H3A 0.9000 . ? N3 H3B 0.9000 . ? N5 C31 1.489(8) . ? N5 C32 1.494(8) . ? N5 H5A 0.9000 . ? N5 H5B 0.9000 . ? N7 O8 1.247(5) . ? N7 O9 1.266(5) . ? C7 C8 1.371(9) . ? C7 C6 1.389(9) . ? C7 C9 1.513(8) . ? N1 C1 1.500(9) . ? N1 C12 1.513(8) . ? N1 C23 1.518(8) . ? C25 C26 1.382(9) . ? C25 C30 1.389(8) . ? C26 C27 1.395(9) . ? C26 H26 0.9300 . ? C8 C3 1.386(8) . ? C8 H8 0.9300 . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? N8 O10 1.235(7) . ? N8 O11 1.240(6) . ? N8 O12 1.259(8) . ? C18 C17 1.396(9) . ? C18 C19 1.404(9) . ? C18 C20 1.490(9) . ? C11 C10 1.520(9) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C3 C4 1.384(8) . ? C29 C30 1.384(9) . ? C29 C28 1.389(9) . ? C29 C31 1.507(9) . ? C19 C14 1.385(8) . ? C19 H19 0.9300 . ? C21 C22 1.502(9) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C28 C27 1.372(9) . ? C28 H28 0.9300 . ? C14 C15 1.371(9) . ? C2 C1 1.529(9) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C4 C5 1.384(9) . ? C4 H4 0.9300 . ? C32 C33 1.500(9) . ? C32 H32A 0.9700 . ? C32 H32B 0.9700 . ? C6 C5 1.370(9) . ? C6 H6 0.9300 . ? C13 C12 1.508(10) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C27 H27 0.9300 . ? C30 H30 0.9300 . ? C5 H5 0.9300 . ? C16 C17 1.355(9) . ? C16 C15 1.438(10) . ? C16 H16 0.9300 . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C24 C23 1.502(9) . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C33 H33A 0.9700 . ? C33 H33B 0.9700 . ? C17 H17 0.9300 . ? C15 H15 0.9300 . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C31 H31A 0.9700 . ? C31 H31B 0.9700 . ? 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 C14 O2 C13 117.7(5) . . ? C3 O1 C2 116.9(5) . . ? C25 O3 C24 117.8(5) . . ? C11 N2 C22 111.1(5) . . ? C11 N2 C33 111.4(5) . . ? C22 N2 C33 109.4(5) . . ? C11 N2 H2 108.3 . . ? C22 N2 H2 108.3 . . ? C33 N2 H2 108.3 . . ? C20 N4 C21 115.5(5) . . ? C20 N4 H4A 108.4 . . ? C21 N4 H4A 108.4 . . ? C20 N4 H4B 108.4 . . ? C21 N4 H4B 108.4 . . ? H4A N4 H4B 107.5 . . ? C10 N3 C9 113.2(5) . . ? C10 N3 H3A 108.9 . . ? C9 N3 H3A 108.9 . . ? C10 N3 H3B 108.9 . . ? C9 N3 H3B 108.9 . . ? H3A N3 H3B 107.7 . . ? C31 N5 C32 112.3(5) . . ? C31 N5 H5A 109.2 . . ? C32 N5 H5A 109.1 . . ? C31 N5 H5B 109.1 . . ? C32 N5 H5B 109.1 . . ? H5A N5 H5B 107.9 . . ? O7 N7 O8 124.5(4) . . ? O7 N7 O9 116.9(4) . . ? O8 N7 O9 118.6(4) . . ? C8 C7 C6 120.9(6) . . ? C8 C7 C9 118.2(5) . . ? C6 C7 C9 120.9(5) . . ? C1 N1 C12 111.5(5) . . ? C1 N1 C23 110.3(5) . . ? C12 N1 C23 110.7(5) . . ? O3 C25 C26 124.3(5) . . ? O3 C25 C30 115.5(5) . . ? C26 C25 C30 120.2(6) . . ? C25 C26 C27 119.2(6) . . ? C25 C26 H26 120.4 . . ? C27 C26 H26 120.4 . . ? C7 C8 C3 119.6(6) . . ? C7 C8 H8 120.2 . . ? C3 C8 H8 120.2 . . ? N3 C9 C7 112.0(5) . . ? N3 C9 H9A 109.2 . . ? C7 C9 H9A 109.2 . . ? N3 C9 H9B 109.2 . . ? C7 C9 H9B 109.2 . . ? H9A C9 H9B 107.9 . . ? O10 N8 O11 122.4(5) . . ? O10 N8 O12 118.8(6) . . ? O11 N8 O12 118.1(5) . . ? C17 C18 C19 118.1(6) . . ? C17 C18 C20 122.3(6) . . ? C19 C18 C20 119.7(6) . . ? N2 C11 C10 114.0(5) . . ? N2 C11 H11A 108.7 . . ? C10 C11 H11A 108.8 . . ? N2 C11 H11B 108.7 . . ? C10 C11 H11B 108.7 . . ? H11A C11 H11B 107.6 . . ? O4 N6 O5 121.0(6) . . ? O4 N6 O6 119.9(6) . . ? O5 N6 O6 119.1(6) . . ? C4 C3 C8 120.3(5) . . ? C4 C3 O1 124.0(5) . . ? C8 C3 O1 115.7(5) . . ? C30 C29 C28 118.8(6) . . ? C30 C29 C31 120.6(6) . . ? C28 C29 C31 120.5(6) . . ? C14 C19 C18 120.6(6) . . ? C14 C19 H19 119.7 . . ? C18 C19 H19 119.7 . . ? N4 C21 C22 111.9(5) . . ? N4 C21 H21A 109.2 . . ? C22 C21 H21A 109.2 . . ? N4 C21 H21B 109.2 . . ? C22 C21 H21B 109.2 . . ? H21A C21 H21B 107.9 . . ? C27 C28 C29 120.8(6) . . ? C27 C28 H28 119.6 . . ? C29 C28 H28 119.6 . . ? C15 C14 O2 123.0(6) . . ? C15 C14 C19 121.2(6) . . ? O2 C14 C19 115.8(5) . . ? O1 C2 C1 105.1(5) . . ? O1 C2 H2A 110.7 . . ? C1 C2 H2A 110.7 . . ? O1 C2 H2B 110.7 . . ? C1 C2 H2B 110.7 . . ? H2A C2 H2B 108.8 . . ? C5 C4 C3 119.0(6) . . ? C5 C4 H4 120.5 . . ? C3 C4 H4 120.5 . . ? N5 C32 C33 111.7(5) . . ? N5 C32 H32A 109.3 . . ? C33 C32 H32A 109.3 . . ? N5 C32 H32B 109.3 . . ? C33 C32 H32B 109.3 . . ? H32A C32 H32B 107.9 . . ? C5 C6 C7 118.8(6) . . ? C5 C6 H6 120.6 . . ? C7 C6 H6 120.6 . . ? O2 C13 C12 107.1(5) . . ? O2 C13 H13A 110.3 . . ? C12 C13 H13A 110.3 . . ? O2 C13 H13B 110.3 . . ? C12 C13 H13B 110.3 . . ? H13A C13 H13B 108.6 . . ? N2 C22 C21 111.8(5) . . ? N2 C22 H22A 109.3 . . ? C21 C22 H22A 109.3 . . ? N2 C22 H22B 109.3 . . ? C21 C22 H22B 109.3 . . ? H22A C22 H22B 107.9 . . ? C28 C27 C26 120.3(6) . . ? C28 C27 H27 119.8 . . ? C26 C27 H27 119.8 . . ? C29 C30 C25 120.6(6) . . ? C29 C30 H30 119.7 . . ? C25 C30 H30 119.7 . . ? C6 C5 C4 121.5(6) . . ? C6 C5 H5 119.3 . . ? C4 C5 H5 119.3 . . ? C17 C16 C15 120.2(6) . . ? C17 C16 H16 119.9 . . ? C15 C16 H16 119.9 . . ? N4 C20 C18 111.5(5) . . ? N4 C20 H20A 109.3 . . ? C18 C20 H20A 109.3 . . ? N4 C20 H20B 109.3 . . ? C18 C20 H20B 109.3 . . ? H20A C20 H20B 108.0 . . ? N1 C1 C2 112.2(5) . . ? N1 C1 H1A 109.2 . . ? C2 C1 H1A 109.2 . . ? N1 C1 H1B 109.2 . . ? C2 C1 H1B 109.2 . . ? H1A C1 H1B 107.9 . . ? O3 C24 C23 105.8(5) . . ? O3 C24 H24A 110.6 . . ? C23 C24 H24A 110.6 . . ? O3 C24 H24B 110.6 . . ? C23 C24 H24B 110.6 . . ? H24A C24 H24B 108.7 . . ? C13 C12 N1 111.4(5) . . ? C13 C12 H12A 109.3 . . ? N1 C12 H12A 109.3 . . ? C13 C12 H12B 109.3 . . ? N1 C12 H12B 109.3 . . ? H12A C12 H12B 108.0 . . ? N2 C33 C32 113.2(5) . . ? N2 C33 H33A 108.9 . . ? C32 C33 H33A 108.9 . . ? N2 C33 H33B 108.9 . . ? C32 C33 H33B 108.9 . . ? H33A C33 H33B 107.7 . . ? C16 C17 C18 121.6(6) . . ? C16 C17 H17 119.2 . . ? C18 C17 H17 119.2 . . ? C14 C15 C16 118.2(6) . . ? C14 C15 H15 120.9 . . ? C16 C15 H15 120.9 . . ? N3 C10 C11 112.3(5) . . ? N3 C10 H10A 109.1 . . ? C11 C10 H10A 109.1 . . ? N3 C10 H10B 109.1 . . ? C11 C10 H10B 109.1 . . ? H10A C10 H10B 107.9 . . ? C24 C23 N1 110.5(5) . . ? C24 C23 H23A 109.5 . . ? N1 C23 H23A 109.5 . . ? C24 C23 H23B 109.5 . . ? N1 C23 H23B 109.5 . . ? H23A C23 H23B 108.1 . . ? N5 C31 C29 112.2(5) . . ? N5 C31 H31A 109.2 . . ? C29 C31 H31A 109.2 . . ? N5 C31 H31B 109.2 . . ? C29 C31 H31B 109.2 . . ? H31A C31 H31B 107.9 . . ? 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 C24 O3 C25 C26 1.0(9) . . . . ? C24 O3 C25 C30 179.3(5) . . . . ? O3 C25 C26 C27 178.0(5) . . . . ? C30 C25 C26 C27 -0.2(9) . . . . ? C6 C7 C8 C3 -0.6(9) . . . . ? C9 C7 C8 C3 177.9(5) . . . . ? C10 N3 C9 C7 -172.4(5) . . . . ? C8 C7 C9 N3 89.4(6) . . . . ? C6 C7 C9 N3 -92.1(6) . . . . ? C22 N2 C11 C10 160.4(5) . . . . ? C33 N2 C11 C10 -77.4(6) . . . . ? C7 C8 C3 C4 -0.5(9) . . . . ? C7 C8 C3 O1 -179.7(5) . . . . ? C2 O1 C3 C4 1.9(8) . . . . ? C2 O1 C3 C8 -178.9(5) . . . . ? C17 C18 C19 C14 1.9(9) . . . . ? C20 C18 C19 C14 -178.6(5) . . . . ? C20 N4 C21 C22 -172.9(5) . . . . ? C30 C29 C28 C27 -0.1(9) . . . . ? C31 C29 C28 C27 -176.6(6) . . . . ? C13 O2 C14 C15 -12.7(8) . . . . ? C13 O2 C14 C19 166.9(5) . . . . ? C18 C19 C14 C15 -3.0(9) . . . . ? C18 C19 C14 O2 177.4(5) . . . . ? C3 O1 C2 C1 -179.7(5) . . . . ? C8 C3 C4 C5 1.4(8) . . . . ? O1 C3 C4 C5 -179.5(5) . . . . ? C31 N5 C32 C33 179.0(5) . . . . ? C8 C7 C6 C5 0.8(9) . . . . ? C9 C7 C6 C5 -177.6(5) . . . . ? C14 O2 C13 C12 177.2(5) . . . . ? C11 N2 C22 C21 -84.5(6) . . . . ? C33 N2 C22 C21 152.0(5) . . . . ? N4 C21 C22 N2 -69.2(6) . . . . ? C29 C28 C27 C26 -1.2(9) . . . . ? C25 C26 C27 C28 1.3(9) . . . . ? C28 C29 C30 C25 1.3(8) . . . . ? C31 C29 C30 C25 177.8(5) . . . . ? O3 C25 C30 C29 -179.5(5) . . . . ? C26 C25 C30 C29 -1.2(9) . . . . ? C7 C6 C5 C4 0.1(9) . . . . ? C3 C4 C5 C6 -1.2(9) . . . . ? C21 N4 C20 C18 -175.5(5) . . . . ? C17 C18 C20 N4 -89.5(7) . . . . ? C19 C18 C20 N4 90.9(7) . . . . ? C12 N1 C1 C2 -76.6(7) . . . . ? C23 N1 C1 C2 159.9(5) . . . . ? O1 C2 C1 N1 -63.1(7) . . . . ? C25 O3 C24 C23 -174.4(5) . . . . ? O2 C13 C12 N1 -63.9(7) . . . . ? C1 N1 C12 C13 160.8(5) . . . . ? C23 N1 C12 C13 -76.0(7) . . . . ? C11 N2 C33 C32 156.1(5) . . . . ? C22 N2 C33 C32 -80.7(6) . . . . ? N5 C32 C33 N2 -73.0(7) . . . . ? C15 C16 C17 C18 -0.8(10) . . . . ? C19 C18 C17 C16 0.0(9) . . . . ? C20 C18 C17 C16 -179.5(6) . . . . ? O2 C14 C15 C16 -178.3(5) . . . . ? C19 C14 C15 C16 2.2(9) . . . . ? C17 C16 C15 C14 -0.3(9) . . . . ? C9 N3 C10 C11 -178.7(5) . . . . ? N2 C11 C10 N3 -81.8(6) . . . . ? O3 C24 C23 N1 -58.7(7) . . . . ? C1 N1 C23 C24 -83.4(7) . . . . ? C12 N1 C23 C24 152.7(6) . . . . ? C32 N5 C31 C29 177.3(5) . . . . ? C30 C29 C31 N5 85.5(7) . . . . ? C28 C29 C31 N5 -98.1(7) . . . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 28.40 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.662 _refine_diff_density_min -0.429 _refine_diff_density_rms 0.177 data_Complex6 #TrackingRef 'B924157D_ccdc_754955_754960_cif.txt' _database_code_depnum_ccdc_archive 'CCDC 754960' #TrackingRef 'Complex1-6.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C33 H51 Br N8 O13' _chemical_formula_sum 'C33 H51 Br N8 O13' _chemical_formula_weight 847.73 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' Br Br -0.2901 2.4595 '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' 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 9.733(2) _cell_length_b 24.969(4) _cell_length_c 16.288(3) _cell_angle_alpha 90.00 _cell_angle_beta 96.989(6) _cell_angle_gamma 90.00 _cell_volume 3929.0(13) _cell_formula_units_Z 4 _cell_measurement_temperature 100(1) _cell_measurement_reflns_used ? _cell_measurement_theta_min 2.0 _cell_measurement_theta_max 28.3 _exptl_crystal_description 'rectangular plates' _exptl_crystal_colour colorless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.433 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1776 _exptl_absorpt_coefficient_mu 1.119 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8240 _exptl_absorpt_correction_T_max 0.8501 _exptl_absorpt_process_details 'SADABS 2.10 (Bruker 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(1) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX' _diffrn_measurement_method /w-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 25552 _diffrn_reflns_av_R_equivalents 0.0517 _diffrn_reflns_av_sigmaI/netI 0.0732 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 33 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 28.45 _reflns_number_total 9764 _reflns_number_gt 5558 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART 5.628 (Bruker, 2003)' _computing_cell_refinement 'SAINT 6.45 ( Bruker, 2003)' _computing_data_reduction 'SAINT 6.45 (Bruker, 2003)' _computing_structure_solution SIR-97 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Diamond 2.1e' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0300P)^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 9764 _refine_ls_number_parameters 485 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1093 _refine_ls_R_factor_gt 0.0714 _refine_ls_wR_factor_ref 0.2329 _refine_ls_wR_factor_gt 0.1835 _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_restrained_S_all 1.073 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.78805(12) 0.06910(4) 0.89333(6) 0.0526(4) Uani 1 1 d . . . O2 O 0.7560(4) 0.34919(17) 0.4622(3) 0.0256(10) Uani 1 1 d . . . O6 O 0.8536(5) 0.18694(19) 0.5802(3) 0.0312(11) Uani 1 1 d . . . O4 O 0.6919(4) 0.18206(19) 0.6618(5) 0.0276(10) Uani 1 1 d . . . O5 O 0.6363(5) 0.18533(19) 0.5293(3) 0.0289(10) Uani 1 1 d . . . O3 O 0.8788(5) 0.34099(17) 0.7113(3) 0.0283(10) Uani 1 1 d . . . O8 O 0.1319(5) 0.0968(2) 0.5183(3) 0.0329(12) Uani 1 1 d . . . O1 O 0.4800(5) 0.33984(17) 0.6328(3) 0.0305(11) Uani 1 1 d . . . O7 O 0.0957(5) 0.09476(19) 0.3834(3) 0.0310(11) Uani 1 1 d . . . O9 O 0.3045(5) 0.08352(19) 0.4477(3) 0.0302(11) Uani 1 1 d . . . N1 N 0.7372(6) 0.0657(2) 0.5849(4) 0.0249(11) Uani 1 1 d . . . H1 H 0.7370 0.1020 0.5891 0.030 Uiso 1 1 calc R . . N3 N 0.4416(5) 0.1224(2) 0.6030(4) 0.0255(12) Uani 1 1 d . . . H3A H 0.5072 0.1431 0.5846 0.031 Uiso 1 1 calc R . . H3B H 0.3803 0.1135 0.5592 0.031 Uiso 1 1 calc R . . N5 N 0.9089(5) 0.1217(2) 0.7380(3) 0.0244(11) Uani 1 1 d . . . H5A H 0.8710 0.1090 0.7818 0.029 Uiso 1 1 calc R . . H5B H 0.8437 0.1409 0.7070 0.029 Uiso 1 1 calc R . . N6 N 0.7272(4) 0.1845(2) 0.5902(3) 0.0236(12) Uani 1 1 d . . . C26 C 0.9707(6) 0.2101(3) 0.7996(4) 0.0240(13) Uani 1 1 d . . . N4 N 0.8386(5) 0.1329(2) 0.4298(3) 0.0248(11) Uani 1 1 d . . . H4A H 0.9258 0.1223 0.4255 0.030 Uiso 1 1 calc R . . H4B H 0.8398 0.1516 0.4771 0.030 Uiso 1 1 calc R . . C20 C 0.7843(6) 0.2630(3) 0.4103(4) 0.0255(13) Uani 1 1 d . . . H20 H 0.7002 0.2544 0.4286 0.031 Uiso 1 1 calc R . . C19 C 0.8374(6) 0.3146(2) 0.4226(4) 0.0219(12) Uani 1 1 d . . . C8 C 0.3765(6) 0.3012(2) 0.6175(4) 0.0242(13) Uani 1 1 d . . . N7 N 0.1763(5) 0.09187(19) 0.4498(4) 0.0315(11) Uani 1 1 d . . . C30 C 0.8977(6) 0.3014(3) 0.7714(4) 0.0240(13) Uani 1 1 d . . . C12 C 0.7973(7) 0.0490(3) 0.5086(4) 0.0276(14) Uani 1 1 d . . . H12A H 0.7708 0.0122 0.4954 0.033 Uiso 1 1 calc R . . H12B H 0.8975 0.0503 0.5193 0.033 Uiso 1 1 calc R . . C15 C 0.8551(7) 0.2244(3) 0.3712(4) 0.0269(14) Uani 1 1 d . . . N2 N 0.6991(6) 0.4102(2) 0.6058(3) 0.0289(12) Uani 1 1 d . . . C18 C 0.9633(7) 0.3284(3) 0.3947(4) 0.0282(14) Uani 1 1 d . . . H18 H 0.9981 0.3631 0.4006 0.034 Uiso 1 1 calc R . . C31 C 0.9528(6) 0.2532(3) 0.7454(4) 0.0249(13) Uani 1 1 d . . . H31 H 0.9773 0.2502 0.6922 0.030 Uiso 1 1 calc R . . C23 C 0.8237(7) 0.0422(2) 0.6565(4) 0.0283(14) Uani 1 1 d . . . H23A H 0.8540 0.0069 0.6412 0.034 Uiso 1 1 calc R . . H23B H 0.7673 0.0376 0.7012 0.034 Uiso 1 1 calc R . . C4 C 0.3248(7) 0.2074(3) 0.6317(4) 0.0245(13) Uani 1 1 d . . . C3 C 0.3691(7) 0.1538(3) 0.6633(4) 0.0264(13) Uani 1 1 d . . . H3C H 0.2885 0.1339 0.6757 0.032 Uiso 1 1 calc R . . H3D H 0.4307 0.1579 0.7144 0.032 Uiso 1 1 calc R . . C29 C 0.8664(7) 0.3068(3) 0.8505(4) 0.0286(14) Uani 1 1 d . . . H29 H 0.8339 0.3392 0.8686 0.034 Uiso 1 1 calc R . . C22 C 0.6966(8) 0.4313(2) 0.5186(4) 0.0321(16) Uani 1 1 d . . . H22A H 0.7160 0.4694 0.5207 0.038 Uiso 1 1 calc R . . H22B H 0.6047 0.4264 0.4892 0.038 Uiso 1 1 calc R . . C14 C 0.7906(7) 0.1690(3) 0.3583(4) 0.0294(14) Uani 1 1 d . . . H14A H 0.6905 0.1721 0.3527 0.035 Uiso 1 1 calc R . . H14B H 0.8161 0.1536 0.3076 0.035 Uiso 1 1 calc R . . C7 C 0.2434(7) 0.3112(3) 0.5776(4) 0.0263(14) Uani 1 1 d . . . H7 H 0.2170 0.3453 0.5591 0.032 Uiso 1 1 calc R . . C5 C 0.1908(7) 0.2171(3) 0.5921(4) 0.0288(14) Uani 1 1 d . . . H5 H 0.1277 0.1891 0.5830 0.035 Uiso 1 1 calc R . . C32 C 0.8516(8) 0.3936(3) 0.7378(4) 0.0310(15) Uani 1 1 d . . . H32A H 0.9299 0.4071 0.7744 0.037 Uiso 1 1 calc R . . H32B H 0.7707 0.3938 0.7672 0.037 Uiso 1 1 calc R . . C9 C 0.4160(6) 0.2499(2) 0.6434(4) 0.0230(12) Uani 1 1 d . . . H9 H 0.5054 0.2440 0.6690 0.028 Uiso 1 1 calc R . . C2 C 0.5077(8) 0.0721(3) 0.6411(5) 0.0297(16) Uani 1 1 d . . . H2A H 0.4365 0.0477 0.6549 0.039 Uiso 1 1 calc R . . H2B H 0.5665 0.0810 0.6917 0.039 Uiso 1 1 calc R . . C27 C 0.9328(7) 0.2152(3) 0.8788(4) 0.0266(14) Uani 1 1 d . . . H27 H 0.9411 0.1858 0.9141 0.032 Uiso 1 1 calc R . . C33 C 0.8264(8) 0.4279(3) 0.6605(5) 0.0331(16) Uani 1 1 d . . . H33A H 0.8159 0.4650 0.6763 0.040 Uiso 1 1 calc R . . H33B H 0.9060 0.4256 0.6301 0.040 Uiso 1 1 calc R . . C1 C 0.5948(7) 0.0448(3) 0.5799(5) 0.0323(16) Uani 1 1 d . . . H1A H 0.5984 0.0067 0.5909 0.039 Uiso 1 1 calc R . . H1B H 0.5493 0.0500 0.5241 0.039 Uiso 1 1 calc R . . C28 C 0.8844(6) 0.2617(3) 0.9053(4) 0.0284(14) Uani 1 1 d . . . H28 H 0.8626 0.2646 0.9592 0.034 Uiso 1 1 calc R . . C24 C 0.9492(6) 0.0751(2) 0.6877(4) 0.0246(13) Uani 1 1 d . . . H24A H 1.0155 0.0528 0.7215 0.030 Uiso 1 1 calc R . . H24B H 0.9930 0.0881 0.6412 0.030 Uiso 1 1 calc R . . C11 C 0.5669(8) 0.4274(3) 0.6429(5) 0.0319(15) Uani 1 1 d . . . H11A H 0.5821 0.4235 0.7026 0.038 Uiso 1 1 calc R . . H11B H 0.5477 0.4648 0.6304 0.038 Uiso 1 1 calc R . . C25 C 1.0280(6) 0.1587(3) 0.7690(4) 0.0275(14) Uani 1 1 d . . . H25A H 1.0871 0.1415 0.8136 0.033 Uiso 1 1 calc R . . H25B H 1.0830 0.1663 0.7246 0.033 Uiso 1 1 calc R . . C17 C 1.0343(7) 0.2884(3) 0.3579(5) 0.0301(17) Uani 1 1 d . . . H17 H 1.1191 0.2966 0.3401 0.043 Uiso 1 1 calc R . . C16 C 0.9833(7) 0.2366(3) 0.3467(4) 0.0296(15) Uani 1 1 d . . . H16 H 1.0341 0.2105 0.3231 0.036 Uiso 1 1 calc R . . C21 C 0.8011(7) 0.4035(3) 0.4713(4) 0.0309(15) Uani 1 1 d . . . H21A H 0.8033 0.4201 0.4176 0.037 Uiso 1 1 calc R . . H21B H 0.8930 0.4054 0.5018 0.037 Uiso 1 1 calc R . . C13 C 0.7492(7) 0.0846(3) 0.4340(4) 0.0296(14) Uani 1 1 d . . . H13A H 0.7500 0.0638 0.3837 0.036 Uiso 1 1 calc R . . H13B H 0.6547 0.0959 0.4372 0.036 Uiso 1 1 calc R . . C6 C 0.1527(7) 0.2686(3) 0.5665(4) 0.0294(14) Uani 1 1 d . . . H6 H 0.0631 0.2746 0.5412 0.035 Uiso 1 1 calc R . . C10 C 0.4436(8) 0.3938(3) 0.6087(5) 0.0351(16) Uani 1 1 d . . . H10A H 0.3611 0.4051 0.6319 0.042 Uiso 1 1 calc R . . H10B H 0.4270 0.3969 0.5490 0.042 Uiso 1 1 calc R . . N8 N 1.2587(6) -0.0072(2) 0.7661(3) 0.0342(12) Uani 1 1 d . . . O10 O 1.2300(5) 0.0155(4) 0.6973(4) 0.035(3) Uani 1 1 d . . . O11 O 1.1974(6) 0.0087(5) 0.8244(5) 0.037(2) Uani 1 1 d . . . O12 O 1.3628(6) -0.0377(4) 0.7757(5) 0.036(5) Uani 1 1 d . . . OW1 O 1.4039(9) -0.0480(6) 0.9433(7) 0.035(4) 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 Br1 0.0672(9) 0.0367(6) 0.0560(7) -0.0002(4) 0.0196(6) -0.0073(4) O2 0.030(2) 0.017(2) 0.031(2) -0.0025(18) 0.0058(18) 0.0004(17) O6 0.029(2) 0.034(3) 0.031(3) -0.006(2) 0.0068(19) 0.000(2) O4 0.026(2) 0.034(3) 0.024(2) -0.0011(19) 0.0052(18) 0.0013(19) O5 0.027(2) 0.033(3) 0.025(2) -0.0018(19) -0.0034(18) 0.0007(19) O3 0.040(3) 0.020(2) 0.025(2) -0.0025(17) 0.0082(19) -0.0013(19) O8 0.038(3) 0.032(3) 0.030(3) -0.005(2) 0.005(2) -0.002(2) O1 0.035(3) 0.020(2) 0.036(3) -0.0059(19) 0.001(2) -0.0010(19) O7 0.030(2) 0.030(3) 0.032(3) -0.001(2) 0.004(2) 0.001(2) O9 0.031(3) 0.026(2) 0.034(3) 0.008(2) 0.006(2) 0.003(2) N1 0.030(3) 0.016(3) 0.029(3) -0.002(2) 0.004(2) -0.001(2) N3 0.024(3) 0.023(3) 0.031(3) 0.000(2) 0.011(2) 0.000(2) N5 0.020(3) 0.025(3) 0.028(3) 0.001(2) 0.002(2) 0.002(2) N6 0.004(2) 0.055(4) 0.011(2) -0.008(2) 0.0002(16) 0.000(2) C26 0.019(3) 0.029(3) 0.024(3) -0.003(3) 0.002(2) -0.001(2) N4 0.031(3) 0.019(3) 0.024(3) -0.002(2) 0.002(2) 0.002(2) C20 0.021(3) 0.027(3) 0.030(3) 0.005(3) 0.005(2) 0.004(2) C19 0.022(3) 0.024(3) 0.020(3) 0.001(2) 0.003(2) 0.003(2) C8 0.026(3) 0.023(3) 0.025(3) -0.005(2) 0.006(2) 0.000(2) N7 0.035(3) 0.022(2) 0.031(3) 0.005(2) 0.004(2) -0.0009(19) C30 0.027(3) 0.025(3) 0.021(3) -0.002(2) 0.005(2) -0.005(2) C12 0.028(3) 0.023(3) 0.032(4) -0.006(3) 0.002(3) 0.001(2) C15 0.032(3) 0.025(3) 0.021(3) 0.004(3) -0.003(3) 0.002(3) N2 0.033(3) 0.023(3) 0.031(3) -0.004(2) 0.005(2) 0.003(2) C18 0.031(3) 0.031(3) 0.022(3) 0.009(3) 0.003(3) 0.002(3) C31 0.030(3) 0.027(3) 0.018(3) -0.003(2) 0.008(2) -0.002(3) C23 0.031(3) 0.017(3) 0.037(4) 0.002(3) 0.004(3) 0.002(2) C4 0.028(3) 0.025(3) 0.022(3) 0.000(2) 0.011(2) 0.003(3) C3 0.027(3) 0.026(3) 0.028(3) 0.003(3) 0.011(3) 0.002(3) C29 0.028(3) 0.030(3) 0.028(3) -0.005(3) 0.007(3) 0.004(3) C22 0.049(4) 0.014(3) 0.031(4) 0.002(3) -0.002(3) -0.001(3) C14 0.038(4) 0.027(3) 0.022(3) 0.005(3) 0.000(3) 0.002(3) C7 0.032(3) 0.027(3) 0.022(3) 0.002(2) 0.010(3) 0.003(3) C5 0.030(3) 0.035(4) 0.023(3) -0.003(3) 0.011(3) -0.005(3) C32 0.045(4) 0.022(3) 0.027(4) -0.006(3) 0.009(3) -0.001(3) C9 0.024(3) 0.027(3) 0.018(3) 0.002(2) 0.006(2) 0.003(2) C2 0.033(4) 0.024(3) 0.032(4) 0.011(3) 0.006(3) 0.003(3) C27 0.028(3) 0.028(3) 0.024(3) 0.004(3) 0.004(2) -0.001(3) C33 0.038(4) 0.024(3) 0.037(4) -0.006(3) 0.007(3) -0.002(3) C1 0.030(3) 0.020(3) 0.047(4) -0.001(3) 0.003(3) -0.002(3) C28 0.023(3) 0.041(4) 0.023(3) -0.001(3) 0.009(2) -0.004(3) C24 0.022(3) 0.026(3) 0.027(3) 0.001(3) 0.004(2) 0.001(2) C11 0.044(4) 0.019(3) 0.034(4) -0.004(3) 0.009(3) 0.003(3) C25 0.021(3) 0.030(3) 0.030(4) 0.005(3) -0.001(2) 0.001(3) C17 0.029(4) 0.029(5) 0.033(4) 0.010(3) 0.006(3) 0.003(3) C16 0.036(4) 0.033(4) 0.021(3) 0.009(3) 0.009(3) 0.002(3) C21 0.037(4) 0.025(3) 0.032(4) 0.001(3) 0.007(3) -0.003(3) C13 0.036(4) 0.025(3) 0.028(4) -0.004(3) 0.002(3) -0.001(3) C6 0.031(3) 0.036(4) 0.021(3) 0.004(3) 0.005(3) 0.003(3) C10 0.047(4) 0.020(3) 0.039(4) -0.002(3) 0.008(3) 0.005(3) N8 0.040(3) 0.024(3) 0.037(3) 0.005(2) 0.003(2) 0.000(2) O10 0.041(6) 0.033(6) 0.032(5) -0.005(4) 0.005(4) 0.001(4) O11 0.043(6) 0.032(5) 0.034(5) -0.004(4) -0.002(4) 0.001(4) O12 0.040(5) 0.031(5) 0.035(5) -0.003(4) -0.005(4) 0.003(4) OW1 0.041(6) 0.031(6) 0.033(6) 0.009(5) 0.006(5) 0.002(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O2 C19 1.384(7) . ? O2 C21 1.428(8) . ? O6 N6 1.261(6) . ? O4 N6 1.256(5) . ? O5 N6 1.246(6) . ? O3 C30 1.388(8) . ? O3 C32 1.417(8) . ? O8 N7 1.251(7) . ? O1 C8 1.396(8) . ? O1 C10 1.437(8) . ? O7 N7 1.258(7) . ? O9 N7 1.270(7) . ? N1 C1 1.474(9) . ? N1 C23 1.474(8) . ? N1 C12 1.496(9) . ? N1 H1 0.9100 . ? N3 C3 1.498(8) . ? N3 C2 1.511(8) . ? N3 H3A 0.9000 . ? N3 H3B 0.9000 . ? N5 C24 1.502(8) . ? N5 C25 1.519(8) . ? N5 H5A 0.9000 . ? N5 H5B 0.9000 . ? C26 C31 1.388(9) . ? C26 C27 1.390(9) . ? C26 C25 1.510(9) . ? N4 C13 1.495(8) . ? N4 C14 1.501(8) . ? N4 H4A 0.9000 . ? N4 H4B 0.9000 . ? C20 C15 1.384(9) . ? C20 C19 1.393(9) . ? C20 H20 0.9300 . ? C19 C18 1.401(9) . ? C8 C9 1.388(9) . ? C8 C7 1.399(9) . ? C30 C29 1.366(9) . ? C30 C31 1.403(9) . ? C12 C13 1.531(10) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C15 C16 1.389(10) . ? C15 C14 1.523(9) . ? N2 C33 1.502(9) . ? N2 C22 1.513(9) . ? N2 C11 1.548(9) . ? C18 C17 1.392(10) . ? C18 H18 0.9300 . ? C31 H31 0.9300 . ? C23 C24 1.508(9) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C4 C9 1.381(9) . ? C4 C5 1.405(9) . ? C4 C3 1.479(9) . ? C3 H3C 0.9700 . ? C3 H3D 0.9700 . ? C29 C28 1.435(10) . ? C29 H29 0.9300 . ? C22 C21 1.516(10) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C7 C6 1.380(9) . ? C7 H7 0.9300 . ? C5 C6 1.388(10) . ? C5 H5 0.9300 . ? C32 C33 1.518(10) . ? C32 H32A 0.9700 . ? C32 H32B 0.9700 . ? C9 H9 0.9300 . ? C2 C1 1.543(10) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C27 C28 1.344(10) . ? C27 H27 0.9300 . ? C33 H33A 0.9700 . ? C33 H33B 0.9700 . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C28 H28 0.9300 . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C11 C10 1.512(10) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C17 C16 1.389(10) . ? C17 H17 0.9300 . ? C16 H16 0.9300 . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C6 H6 0.9300 . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? N8 O11 1.247(5) . ? N8 O10 1.256(5) . ? N8 O12 1.263(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 C19 O2 C21 117.1(5) . . ? C30 O3 C32 117.3(5) . . ? C8 O1 C10 116.9(5) . . ? C1 N1 C23 110.2(5) . . ? C1 N1 C12 108.4(5) . . ? C23 N1 C12 107.7(5) . . ? C1 N1 H1 110.2 . . ? C23 N1 H1 110.2 . . ? C12 N1 H1 110.2 . . ? C3 N3 C2 112.1(5) . . ? C3 N3 H3A 109.2 . . ? C2 N3 H3A 109.2 . . ? C3 N3 H3B 109.2 . . ? C2 N3 H3B 109.2 . . ? H3A N3 H3B 107.9 . . ? C24 N5 C25 114.4(5) . . ? C24 N5 H5A 108.7 . . ? C25 N5 H5A 108.7 . . ? C24 N5 H5B 108.7 . . ? C25 N5 H5B 108.7 . . ? H5A N5 H5B 107.6 . . ? O5 N6 O4 119.4(5) . . ? O5 N6 O6 120.4(5) . . ? O4 N6 O6 120.2(5) . . ? C31 C26 C27 119.5(6) . . ? C31 C26 C25 118.2(6) . . ? C27 C26 C25 122.2(6) . . ? C13 N4 C14 113.1(5) . . ? C13 N4 H4A 109.0 . . ? C14 N4 H4A 109.0 . . ? C13 N4 H4B 109.0 . . ? C14 N4 H4B 109.0 . . ? H4A N4 H4B 107.8 . . ? C15 C20 C19 120.8(6) . . ? C15 C20 H20 119.6 . . ? C19 C20 H20 119.6 . . ? O2 C19 C20 114.9(5) . . ? O2 C19 C18 124.8(6) . . ? C20 C19 C18 120.3(6) . . ? C9 C8 O1 114.7(5) . . ? C9 C8 C7 120.8(6) . . ? O1 C8 C7 124.5(6) . . ? O8 N7 O7 120.9(5) . . ? O8 N7 O9 119.2(6) . . ? O7 N7 O9 119.9(6) . . ? C29 C30 O3 124.7(6) . . ? C29 C30 C31 120.4(6) . . ? O3 C30 C31 114.8(5) . . ? N1 C12 C13 112.6(5) . . ? N1 C12 H12A 109.1 . . ? C13 C12 H12A 109.1 . . ? N1 C12 H12B 109.1 . . ? C13 C12 H12B 109.1 . . ? H12A C12 H12B 107.8 . . ? C20 C15 C16 119.7(6) . . ? C20 C15 C14 118.4(6) . . ? C16 C15 C14 121.9(6) . . ? C33 N2 C22 111.9(6) . . ? C33 N2 C11 110.6(5) . . ? C22 N2 C11 110.6(5) . . ? C17 C18 C19 117.6(6) . . ? C17 C18 H18 121.2 . . ? C19 C18 H18 121.2 . . ? C26 C31 C30 119.7(6) . . ? C26 C31 H31 120.1 . . ? C30 C31 H31 120.1 . . ? N1 C23 C24 114.2(5) . . ? N1 C23 H23A 108.7 . . ? C24 C23 H23A 108.7 . . ? N1 C23 H23B 108.7 . . ? C24 C23 H23B 108.7 . . ? H23A C23 H23B 107.6 . . ? C9 C4 C5 118.4(6) . . ? C9 C4 C3 119.5(6) . . ? C5 C4 C3 122.1(6) . . ? C4 C3 N3 112.7(5) . . ? C4 C3 H3C 109.1 . . ? N3 C3 H3C 109.1 . . ? C4 C3 H3D 109.1 . . ? N3 C3 H3D 109.1 . . ? H3C C3 H3D 107.8 . . ? C30 C29 C28 119.0(6) . . ? C30 C29 H29 120.5 . . ? C28 C29 H29 120.5 . . ? N2 C22 C21 112.5(5) . . ? N2 C22 H22A 109.1 . . ? C21 C22 H22A 109.1 . . ? N2 C22 H22B 109.1 . . ? C21 C22 H22B 109.1 . . ? H22A C22 H22B 107.8 . . ? N4 C14 C15 110.7(5) . . ? N4 C14 H14A 109.5 . . ? C15 C14 H14A 109.5 . . ? N4 C14 H14B 109.5 . . ? C15 C14 H14B 109.5 . . ? H14A C14 H14B 108.1 . . ? C6 C7 C8 117.7(6) . . ? C6 C7 H7 121.2 . . ? C8 C7 H7 121.2 . . ? C6 C5 C4 119.8(6) . . ? C6 C5 H5 120.1 . . ? C4 C5 H5 120.1 . . ? O3 C32 C33 106.8(5) . . ? O3 C32 H32A 110.4 . . ? C33 C32 H32A 110.4 . . ? O3 C32 H32B 110.4 . . ? C33 C32 H32B 110.4 . . ? H32A C32 H32B 108.6 . . ? C4 C9 C8 121.2(6) . . ? C4 C9 H9 119.4 . . ? C8 C9 H9 119.4 . . ? N3 C2 C1 109.9(6) . . ? N3 C2 H2A 109.7 . . ? C1 C2 H2A 109.7 . . ? N3 C2 H2B 109.7 . . ? C1 C2 H2B 109.7 . . ? H2A C2 H2B 108.2 . . ? C28 C27 C26 121.3(6) . . ? C28 C27 H27 119.3 . . ? C26 C27 H27 119.3 . . ? N2 C33 C32 111.3(6) . . ? N2 C33 H33A 109.4 . . ? C32 C33 H33A 109.4 . . ? N2 C33 H33B 109.4 . . ? C32 C33 H33B 109.4 . . ? H33A C33 H33B 108.0 . . ? N1 C1 C2 113.3(6) . . ? N1 C1 H1A 108.9 . . ? C2 C1 H1A 108.9 . . ? N1 C1 H1B 108.9 . . ? C2 C1 H1B 108.9 . . ? H1A C1 H1B 107.7 . . ? C27 C28 C29 120.0(6) . . ? C27 C28 H28 120.0 . . ? C29 C28 H28 120.0 . . ? N5 C24 C23 110.5(5) . . ? N5 C24 H24A 109.5 . . ? C23 C24 H24A 109.5 . . ? N5 C24 H24B 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 108.1 . . ? C10 C11 N2 111.3(5) . . ? C10 C11 H11A 109.4 . . ? N2 C11 H11A 109.4 . . ? C10 C11 H11B 109.4 . . ? N2 C11 H11B 109.4 . . ? H11A C11 H11B 108.0 . . ? C26 C25 N5 109.3(5) . . ? C26 C25 H25A 109.8 . . ? N5 C25 H25A 109.8 . . ? C26 C25 H25B 109.8 . . ? N5 C25 H25B 109.8 . . ? H25A C25 H25B 108.3 . . ? C16 C17 C18 122.4(6) . . ? C16 C17 H17 118.8 . . ? C18 C17 H17 118.8 . . ? C17 C16 C15 119.0(6) . . ? C17 C16 H16 120.5 . . ? C15 C16 H16 120.5 . . ? O2 C21 C22 105.7(5) . . ? O2 C21 H21A 110.6 . . ? C22 C21 H21A 110.6 . . ? O2 C21 H21B 110.6 . . ? C22 C21 H21B 110.6 . . ? H21A C21 H21B 108.7 . . ? N4 C13 C12 112.5(5) . . ? N4 C13 H13A 109.1 . . ? C12 C13 H13A 109.1 . . ? N4 C13 H13B 109.1 . . ? C12 C13 H13B 109.1 . . ? H13A C13 H13B 107.8 . . ? C7 C6 C5 122.1(6) . . ? C7 C6 H6 119.0 . . ? C5 C6 H6 119.0 . . ? O1 C10 C11 105.1(6) . . ? O1 C10 H10A 110.7 . . ? C11 C10 H10A 110.7 . . ? O1 C10 H10B 110.7 . . ? C11 C10 H10B 110.7 . . ? H10A C10 H10B 108.8 . . ? O11 N8 O10 117.5(4) . . ? O11 N8 O12 123.3(4) . . ? O10 N8 O12 118.1(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C21 O2 C19 C20 -175.9(5) . . . . ? C21 O2 C19 C18 3.2(9) . . . . ? C15 C20 C19 O2 179.8(5) . . . . ? C15 C20 C19 C18 0.7(9) . . . . ? C10 O1 C8 C9 -178.8(6) . . . . ? C10 O1 C8 C7 2.8(9) . . . . ? C32 O3 C30 C29 13.1(9) . . . . ? C32 O3 C30 C31 -167.1(6) . . . . ? C1 N1 C12 C13 79.8(6) . . . . ? C23 N1 C12 C13 -161.0(5) . . . . ? C19 C20 C15 C16 2.4(9) . . . . ? C19 C20 C15 C14 -179.0(5) . . . . ? O2 C19 C18 C17 178.4(6) . . . . ? C20 C19 C18 C17 -2.6(9) . . . . ? C27 C26 C31 C30 0.4(9) . . . . ? C25 C26 C31 C30 179.0(5) . . . . ? C29 C30 C31 C26 2.5(9) . . . . ? O3 C30 C31 C26 -177.4(5) . . . . ? C1 N1 C23 C24 -156.9(6) . . . . ? C12 N1 C23 C24 85.0(6) . . . . ? C9 C4 C3 N3 -86.9(7) . . . . ? C5 C4 C3 N3 95.1(7) . . . . ? C2 N3 C3 C4 170.1(5) . . . . ? O3 C30 C29 C28 176.8(6) . . . . ? C31 C30 C29 C28 -3.0(9) . . . . ? C33 N2 C22 C21 72.2(7) . . . . ? C11 N2 C22 C21 -164.0(5) . . . . ? C13 N4 C14 C15 162.6(5) . . . . ? C20 C15 C14 N4 -91.3(7) . . . . ? C16 C15 C14 N4 87.2(7) . . . . ? C9 C8 C7 C6 1.3(9) . . . . ? O1 C8 C7 C6 179.6(6) . . . . ? C9 C4 C5 C6 -0.6(9) . . . . ? C3 C4 C5 C6 177.4(6) . . . . ? C30 O3 C32 C33 -176.5(5) . . . . ? C5 C4 C9 C8 0.6(9) . . . . ? C3 C4 C9 C8 -177.5(6) . . . . ? O1 C8 C9 C4 -179.5(6) . . . . ? C7 C8 C9 C4 -1.0(10) . . . . ? C3 N3 C2 C1 -173.5(5) . . . . ? C31 C26 C27 C28 -2.8(10) . . . . ? C25 C26 C27 C28 178.7(6) . . . . ? C22 N2 C33 C32 -162.0(6) . . . . ? C11 N2 C33 C32 74.2(7) . . . . ? O3 C32 C33 N2 64.3(7) . . . . ? C23 N1 C1 C2 78.8(7) . . . . ? C12 N1 C1 C2 -163.6(5) . . . . ? N3 C2 C1 N1 86.4(7) . . . . ? C26 C27 C28 C29 2.2(10) . . . . ? C30 C29 C28 C27 0.7(10) . . . . ? C25 N5 C24 C23 -177.4(5) . . . . ? N1 C23 C24 N5 77.6(7) . . . . ? C33 N2 C11 C10 -158.9(6) . . . . ? C22 N2 C11 C10 76.5(7) . . . . ? C31 C26 C25 N5 -95.0(7) . . . . ? C27 C26 C25 N5 83.5(7) . . . . ? C24 N5 C25 C26 166.1(5) . . . . ? C19 C18 C17 C16 1.5(10) . . . . ? C18 C17 C16 C15 1.6(10) . . . . ? C20 C15 C16 C17 -3.5(9) . . . . ? C14 C15 C16 C17 178.0(6) . . . . ? C19 O2 C21 C22 -178.2(5) . . . . ? N2 C22 C21 O2 65.7(7) . . . . ? C14 N4 C13 C12 -178.4(5) . . . . ? N1 C12 C13 N4 87.0(7) . . . . ? C8 C7 C6 C5 -1.3(10) . . . . ? C4 C5 C6 C7 1.0(10) . . . . ? C8 O1 C10 C11 172.4(5) . . . . ? N2 C11 C10 O1 61.0(7) . . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 28.45 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.691 _refine_diff_density_min -0.443 _refine_diff_density_rms 0.239