# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2005 data_global _journal_coden_Cambridge 177 _publ_contact_author_name 'Prof. Anunay Samanta' _publ_contact_author_address ; School of Chemistry University of Hyderabad Hyderabad - 500 046 India ; _publ_contact_author_email assc@uohyd,ernet.in _publ_contact_author_phone +91(40)23011594 _publ_contact_author_fax +91(40)23012460 loop_ _publ_author_name _publ_author_address S.Banthia ;School of Chemistry University of Hyderabad Hyderabad - 500 046 India ; A.Samanta ;School of Chemistry University of Hyderabad Hyderabad - 500 046 India ; _publ_requested_journal 'Organic & Biomolecular Chemistry' _publ_section_title ; Calix[4]azacrown and 4-Aminophthalimide-Appended Calix[4]azacrown: Synthesis, Structure, Complexation and Fluorescence Signaling Behaviour ; data_L _database_code_depnum_ccdc_archive 'CCDC 257059' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C36 H37 N3 O6, C H4 O' _chemical_formula_sum 'C37 H41 N3 O7' _chemical_formula_weight 639.73 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.470(8) _cell_length_b 15.549(8) _cell_length_c 16.864(3) _cell_angle_alpha 90.00 _cell_angle_beta 98.63(4) _cell_angle_gamma 90.00 _cell_volume 3233(3) _cell_formula_units_Z 4 _cell_measurement_temperature 298 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 5.41 _cell_measurement_theta_max 10.17 _exptl_crystal_description rectangular _exptl_crystal_colour colorless _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.32 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.314 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1360 _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf Nonius Mach3 four circle (CAD4)' _diffrn_measurement_method 'Profile data from omega' _diffrn_standards_number 3 _diffrn_standards_interval_time 90 _diffrn_standards_decay_% none _diffrn_reflns_number 5676 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.2399 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.79 _diffrn_reflns_theta_max 24.98 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.98 _diffrn_measured_fraction_theta_full 0.999 _reflns_number_total 5676 _reflns_number_gt 1765 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4 Software (Enraf nonius, 1989)' _computing_cell_refinement CAD4 _computing_data_reduction 'Wingx (Farrugia 2002)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows/Platon' _computing_publication_material 'WinGX publication routines (Farrugia, 2002)' _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^)+(0.0305P)^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 5676 _refine_ls_number_parameters 429 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.2698 _refine_ls_R_factor_gt 0.0654 _refine_ls_wR_factor_ref 0.1298 _refine_ls_wR_factor_gt 0.0855 _refine_ls_goodness_of_fit_ref 0.960 _refine_ls_restrained_S_all 0.960 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.216 _refine_diff_density_min -0.239 _refine_diff_density_rms 0.053 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.7787(3) 0.2123(2) 0.12461(18) 0.0380(10) Uani 1 1 d . . . O2 O 0.5950(3) 0.2205(2) -0.00084(18) 0.0459(10) Uani 1 1 d . . . H2 H 0.6392 0.2024 0.0363 0.069 Uiso 1 1 calc R . . O3 O 0.6541(3) 0.3160(2) -0.13154(19) 0.0370(10) Uani 1 1 d . . . O4 O 0.8020(3) 0.3444(2) 0.01178(19) 0.0478(11) Uani 1 1 d . . . H4 H 0.7727 0.3429 -0.0351 0.072 Uiso 1 1 calc R . . O5 O 0.6755(3) 0.1772(2) -0.2959(2) 0.0679(14) Uani 1 1 d . . . O6 O 0.9813(3) 0.0575(3) 0.1175(2) 0.0843(16) Uani 1 1 d . . . N1 N 0.6496(3) 0.1512(3) -0.1689(3) 0.0407(12) Uani 1 1 d . . . H1 H 0.6370 0.1735 -0.1246 0.049 Uiso 1 1 calc R . . N2 N 0.8396(4) 0.0536(3) -0.0913(3) 0.0475(13) Uani 1 1 d D . . H2A H 0.887(4) 0.009(3) -0.077(3) 0.071 Uiso 1 1 d D . . N3 N 0.9272(3) 0.1722(3) 0.0400(3) 0.0443(13) Uani 1 1 d . . . H3 H 0.8920 0.2199 0.0384 0.053 Uiso 1 1 calc R . . C1 C 0.8988(4) 0.3680(3) 0.1698(3) 0.0448(16) Uani 1 1 d . . . H1A H 0.9272 0.3178 0.1459 0.054 Uiso 1 1 calc R . . H1B H 0.9516 0.3851 0.2153 0.054 Uiso 1 1 calc R . . C2 C 0.8862(4) 0.4405(4) 0.1087(3) 0.0360(14) Uani 1 1 d . . . C3 C 0.9266(4) 0.5205(4) 0.1294(3) 0.0469(17) Uani 1 1 d . . . H3A H 0.9603 0.5306 0.1816 0.056 Uiso 1 1 calc R . . C4 C 0.9183(5) 0.5865(4) 0.0739(4) 0.0553(18) Uani 1 1 d . . . H4A H 0.9488 0.6399 0.0882 0.066 Uiso 1 1 calc R . . C5 C 0.8646(4) 0.5729(4) -0.0026(4) 0.0476(17) Uani 1 1 d . . . H5 H 0.8579 0.6177 -0.0395 0.057 Uiso 1 1 calc R . . C6 C 0.8204(4) 0.4929(4) -0.0253(3) 0.0402(15) Uani 1 1 d . . . C7 C 0.7604(4) 0.4804(3) -0.1090(3) 0.0421(15) Uani 1 1 d . . . H7A H 0.7897 0.4306 -0.1329 0.051 Uiso 1 1 calc R . . H7B H 0.7720 0.5302 -0.1412 0.051 Uiso 1 1 calc R . . C8 C 0.6383(4) 0.4677(4) -0.1102(3) 0.0387(15) Uani 1 1 d . . . C9 C 0.5736(5) 0.5381(4) -0.1000(3) 0.0474(16) Uani 1 1 d . . . H9 H 0.6041 0.5928 -0.0947 0.057 Uiso 1 1 calc R . . C10 C 0.4636(5) 0.5275(4) -0.0977(3) 0.0505(17) Uani 1 1 d . . . H10 H 0.4203 0.5751 -0.0918 0.061 Uiso 1 1 calc R . . C11 C 0.4183(4) 0.4461(4) -0.1041(3) 0.0452(16) Uani 1 1 d . . . H11 H 0.3446 0.4395 -0.1022 0.054 Uiso 1 1 calc R . . C12 C 0.4811(4) 0.3741(4) -0.1132(3) 0.0354(14) Uani 1 1 d . . . C13 C 0.4302(4) 0.2853(3) -0.1151(3) 0.0393(15) Uani 1 1 d . . . H13A H 0.3619 0.2862 -0.1512 0.047 Uiso 1 1 calc R . . H13B H 0.4776 0.2446 -0.1364 0.047 Uiso 1 1 calc R . . C14 C 0.4099(4) 0.2545(3) -0.0334(3) 0.0348(14) Uani 1 1 d . . . C15 C 0.3075(4) 0.2546(3) -0.0127(3) 0.0452(16) Uani 1 1 d . . . H15 H 0.2497 0.2726 -0.0504 0.054 Uiso 1 1 calc R . . C16 C 0.2875(5) 0.2288(4) 0.0626(4) 0.0538(17) Uani 1 1 d . . . H16 H 0.2175 0.2292 0.0755 0.065 Uiso 1 1 calc R . . C17 C 0.3729(5) 0.2029(3) 0.1169(3) 0.0465(16) Uani 1 1 d . . . H17 H 0.3600 0.1865 0.1676 0.056 Uiso 1 1 calc R . . C18 C 0.4795(5) 0.1998(3) 0.1003(3) 0.0378(14) Uani 1 1 d . . . C19 C 0.5715(4) 0.1738(3) 0.1639(3) 0.0440(15) Uani 1 1 d . . . H19A H 0.6187 0.1341 0.1412 0.053 Uiso 1 1 calc R . . H19B H 0.5428 0.1443 0.2069 0.053 Uiso 1 1 calc R . . C20 C 0.6365(4) 0.2511(3) 0.1976(3) 0.0377(15) Uani 1 1 d . . . C21 C 0.5955(5) 0.3072(4) 0.2489(3) 0.0525(18) Uani 1 1 d . . . H21 H 0.5293 0.2954 0.2656 0.063 Uiso 1 1 calc R . . C22 C 0.6518(5) 0.3807(4) 0.2759(3) 0.0584(19) Uani 1 1 d . . . H22 H 0.6242 0.4178 0.3111 0.070 Uiso 1 1 calc R . . C23 C 0.7493(5) 0.3986(4) 0.2502(3) 0.0506(16) Uani 1 1 d . . . H23 H 0.7859 0.4490 0.2672 0.061 Uiso 1 1 calc R . . C24 C 0.7940(4) 0.3433(4) 0.1998(3) 0.0373(15) Uani 1 1 d . . . C25 C 0.7370(5) 0.2690(3) 0.1765(3) 0.0360(14) Uani 1 1 d . . . C26 C 0.4943(4) 0.2249(3) 0.0229(3) 0.0340(14) Uani 1 1 d . . . C27 C 0.5892(5) 0.3874(4) -0.1195(3) 0.0361(14) Uani 1 1 d . . . C28 C 0.8347(4) 0.4270(4) 0.0314(3) 0.0381(15) Uani 1 1 d . . . C29 C 0.8539(4) 0.1504(3) 0.1620(3) 0.0460(16) Uani 1 1 d . . . H29A H 0.8151 0.1014 0.1791 0.055 Uiso 1 1 calc R . . H29B H 0.8969 0.1755 0.2090 0.055 Uiso 1 1 calc R . . C30 C 0.9273(5) 0.1213(4) 0.1040(4) 0.0468(16) Uani 1 1 d . . . C31 C 0.9833(4) 0.1510(4) -0.0267(3) 0.0487(16) Uani 1 1 d . . . H31A H 1.0297 0.1015 -0.0128 0.058 Uiso 1 1 calc R . . H31B H 1.0289 0.1989 -0.0373 0.058 Uiso 1 1 calc R . . C32 C 0.9036(4) 0.1311(4) -0.1014(3) 0.0492(16) Uani 1 1 d . . . H32A H 0.8550 0.1796 -0.1136 0.059 Uiso 1 1 calc R . . H32B H 0.9429 0.1229 -0.1462 0.059 Uiso 1 1 calc R . . C33 C 0.7736(4) 0.0257(3) -0.1665(3) 0.0551(18) Uani 1 1 d . . . H33A H 0.7730 -0.0367 -0.1686 0.066 Uiso 1 1 calc R . . H33B H 0.8068 0.0464 -0.2114 0.066 Uiso 1 1 calc R . . C34 C 0.6575(4) 0.0583(3) -0.1751(3) 0.0489(16) Uani 1 1 d . . . H34A H 0.6190 0.0401 -0.2266 0.059 Uiso 1 1 calc R . . H34B H 0.6219 0.0321 -0.1337 0.059 Uiso 1 1 calc R . . C35 C 0.6614(4) 0.2033(4) -0.2305(4) 0.0436(16) Uani 1 1 d . . . C36 C 0.6589(4) 0.2983(3) -0.2146(3) 0.0484(17) Uani 1 1 d . . . H36A H 0.7233 0.3249 -0.2297 0.058 Uiso 1 1 calc R . . H36B H 0.5962 0.3235 -0.2474 0.058 Uiso 1 1 calc R . . O7 O 0.7022(4) 0.0561(3) 0.0274(3) 0.0829(15) Uani 1 1 d . . . H7 H 0.7511 0.0523 0.0001 0.124 Uiso 1 1 calc R . . C37 C 0.6608(6) -0.0239(4) 0.0377(4) 0.110(3) Uani 1 1 d . . . H37A H 0.7122 -0.0566 0.0737 0.165 Uiso 1 1 calc R . . H37B H 0.6465 -0.0527 -0.0131 0.165 Uiso 1 1 calc R . . H37C H 0.5945 -0.0185 0.0599 0.165 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.044(2) 0.037(2) 0.033(2) -0.0013(19) 0.0048(19) 0.012(2) O2 0.034(2) 0.074(3) 0.030(2) 0.015(2) 0.0059(18) 0.006(2) O3 0.041(2) 0.038(2) 0.033(2) 0.0038(19) 0.0089(19) 0.0101(19) O4 0.062(3) 0.039(3) 0.036(2) 0.002(2) -0.012(2) -0.003(2) O5 0.098(4) 0.070(3) 0.042(3) -0.016(2) 0.030(3) 0.001(3) O6 0.106(4) 0.086(4) 0.069(3) 0.032(3) 0.040(3) 0.074(3) N1 0.048(3) 0.038(3) 0.037(3) -0.002(3) 0.007(2) 0.008(3) N2 0.051(4) 0.042(3) 0.048(3) 0.006(3) 0.003(3) 0.014(3) N3 0.055(3) 0.038(3) 0.041(3) 0.004(3) 0.010(3) 0.019(3) C1 0.046(4) 0.052(4) 0.035(3) -0.008(3) 0.000(3) 0.006(3) C2 0.028(3) 0.039(4) 0.040(4) -0.008(3) 0.001(3) 0.002(3) C3 0.038(4) 0.045(4) 0.054(4) -0.008(4) -0.004(3) 0.000(3) C4 0.055(4) 0.034(4) 0.074(5) 0.001(4) -0.001(4) -0.007(3) C5 0.036(4) 0.043(4) 0.063(5) 0.005(4) 0.004(3) 0.000(3) C6 0.042(4) 0.040(4) 0.040(4) -0.003(3) 0.011(3) -0.006(3) C7 0.058(4) 0.031(4) 0.039(4) 0.009(3) 0.014(3) 0.003(3) C8 0.040(4) 0.039(4) 0.037(4) 0.007(3) 0.006(3) 0.004(3) C9 0.055(4) 0.039(4) 0.045(4) 0.004(3) -0.002(3) -0.007(4) C10 0.061(5) 0.040(4) 0.049(4) -0.002(3) 0.003(4) 0.018(4) C11 0.034(4) 0.053(4) 0.046(4) 0.002(3) 0.001(3) 0.014(4) C12 0.039(4) 0.040(4) 0.025(3) 0.004(3) -0.002(3) 0.004(3) C13 0.033(4) 0.047(4) 0.036(3) -0.004(3) -0.001(3) 0.000(3) C14 0.035(4) 0.031(4) 0.039(3) -0.009(3) 0.007(3) -0.002(3) C15 0.033(4) 0.048(4) 0.054(4) -0.004(3) 0.005(3) -0.001(3) C16 0.036(4) 0.059(5) 0.070(5) -0.001(4) 0.019(4) -0.006(3) C17 0.051(4) 0.045(4) 0.048(4) -0.005(3) 0.023(4) -0.006(3) C18 0.047(4) 0.031(4) 0.037(4) 0.003(3) 0.012(3) -0.005(3) C19 0.052(4) 0.046(4) 0.037(4) 0.003(3) 0.013(3) 0.001(3) C20 0.043(4) 0.039(4) 0.030(3) 0.003(3) 0.004(3) 0.005(3) C21 0.051(4) 0.064(5) 0.046(4) -0.008(4) 0.018(3) 0.000(4) C22 0.076(5) 0.055(5) 0.049(4) -0.024(4) 0.028(4) 0.002(4) C23 0.058(4) 0.051(4) 0.043(4) -0.015(3) 0.007(3) -0.009(4) C24 0.041(4) 0.045(4) 0.025(3) 0.006(3) 0.002(3) 0.010(3) C25 0.045(4) 0.037(4) 0.024(3) 0.000(3) -0.002(3) 0.012(3) C26 0.027(3) 0.029(3) 0.048(4) -0.002(3) 0.012(3) 0.003(3) C27 0.041(4) 0.034(4) 0.032(4) -0.001(3) 0.003(3) 0.012(3) C28 0.040(4) 0.033(4) 0.042(4) -0.008(3) 0.008(3) -0.003(3) C29 0.056(4) 0.040(4) 0.041(4) 0.005(3) 0.006(3) 0.015(3) C30 0.038(4) 0.054(5) 0.046(4) 0.001(4) 0.000(3) 0.016(4) C31 0.037(4) 0.057(4) 0.055(4) -0.003(4) 0.015(3) -0.001(3) C32 0.046(4) 0.058(4) 0.046(4) 0.001(3) 0.014(3) 0.009(4) C33 0.060(4) 0.045(4) 0.058(4) -0.011(4) 0.003(4) 0.011(4) C34 0.057(4) 0.036(4) 0.051(4) -0.004(3) 0.002(3) 0.006(3) C35 0.039(4) 0.049(4) 0.042(4) -0.001(4) 0.006(3) 0.004(3) C36 0.062(4) 0.054(4) 0.033(4) 0.002(3) 0.020(3) 0.011(3) O7 0.095(4) 0.061(3) 0.101(4) -0.029(3) 0.043(3) -0.014(3) C37 0.202(10) 0.070(6) 0.068(5) -0.003(5) 0.054(6) -0.021(6) _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 C25 1.396(5) . ? O1 C29 1.423(5) . ? O2 C26 1.376(5) . ? O2 H2 0.8200 . ? O3 C27 1.405(5) . ? O3 C36 1.438(5) . ? O4 C28 1.372(5) . ? O4 H4 0.8200 . ? O5 C35 1.213(6) . ? O6 C30 1.202(6) . ? N1 C35 1.342(6) . ? N1 C34 1.453(5) . ? N1 H1 0.8600 . ? N2 C32 1.470(6) . ? N2 C33 1.470(6) . ? N2 H2A 0.92(4) . ? N3 C30 1.338(6) . ? N3 C31 1.449(5) . ? N3 H3 0.8600 . ? C1 C24 1.520(6) . ? C1 C2 1.521(6) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 C3 1.368(6) . ? C2 C28 1.379(6) . ? C3 C4 1.381(6) . ? C3 H3A 0.9300 . ? C4 C5 1.379(6) . ? C4 H4A 0.9300 . ? C5 C6 1.391(7) . ? C5 H5 0.9300 . ? C6 C28 1.395(7) . ? C6 C7 1.507(6) . ? C7 C8 1.532(6) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.386(6) . ? C8 C27 1.389(6) . ? C9 C10 1.388(7) . ? C9 H9 0.9300 . ? C10 C11 1.384(6) . ? C10 H10 0.9300 . ? C11 C12 1.388(6) . ? C11 H11 0.9300 . ? C12 C27 1.384(6) . ? C12 C13 1.518(6) . ? C13 C14 1.515(6) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C15 1.372(6) . ? C14 C26 1.386(6) . ? C15 C16 1.391(6) . ? C15 H15 0.9300 . ? C16 C17 1.357(7) . ? C16 H16 0.9300 . ? C17 C18 1.399(6) . ? C17 H17 0.9300 . ? C18 C26 1.401(6) . ? C18 C19 1.504(6) . ? C19 C20 1.512(6) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 C21 1.379(6) . ? C20 C25 1.382(6) . ? C21 C22 1.383(7) . ? C21 H21 0.9300 . ? C22 C23 1.378(7) . ? C22 H22 0.9300 . ? C23 C24 1.384(6) . ? C23 H23 0.9300 . ? C24 C25 1.382(7) . ? C29 C30 1.506(6) . ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? C31 C32 1.514(6) . ? C31 H31A 0.9700 . ? C31 H31B 0.9700 . ? C32 H32A 0.9700 . ? C32 H32B 0.9700 . ? C33 C34 1.521(6) . ? C33 H33A 0.9700 . ? C33 H33B 0.9700 . ? C34 H34A 0.9700 . ? C34 H34B 0.9700 . ? C35 C36 1.503(6) . ? C36 H36A 0.9700 . ? C36 H36B 0.9700 . ? O7 C37 1.367(6) . ? O7 H7 0.8200 . ? C37 H37A 0.9600 . ? C37 H37B 0.9600 . ? C37 H37C 0.9600 . ? 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 C25 O1 C29 115.6(4) . . ? C26 O2 H2 109.5 . . ? C27 O3 C36 113.6(4) . . ? C28 O4 H4 109.5 . . ? C35 N1 C34 121.9(5) . . ? C35 N1 H1 119.0 . . ? C34 N1 H1 119.0 . . ? C32 N2 C33 112.6(4) . . ? C32 N2 H2A 108(3) . . ? C33 N2 H2A 105(3) . . ? C30 N3 C31 123.3(5) . . ? C30 N3 H3 118.4 . . ? C31 N3 H3 118.4 . . ? C24 C1 C2 113.9(4) . . ? C24 C1 H1A 108.8 . . ? C2 C1 H1A 108.8 . . ? C24 C1 H1B 108.8 . . ? C2 C1 H1B 108.8 . . ? H1A C1 H1B 107.7 . . ? C3 C2 C28 118.8(6) . . ? C3 C2 C1 120.3(5) . . ? C28 C2 C1 120.9(5) . . ? C2 C3 C4 121.0(5) . . ? C2 C3 H3A 119.5 . . ? C4 C3 H3A 119.5 . . ? C5 C4 C3 119.7(6) . . ? C5 C4 H4A 120.1 . . ? C3 C4 H4A 120.1 . . ? C4 C5 C6 120.8(6) . . ? C4 C5 H5 119.6 . . ? C6 C5 H5 119.6 . . ? C5 C6 C28 117.6(5) . . ? C5 C6 C7 119.6(5) . . ? C28 C6 C7 122.8(5) . . ? C6 C7 C8 112.5(4) . . ? C6 C7 H7A 109.1 . . ? C8 C7 H7A 109.1 . . ? C6 C7 H7B 109.1 . . ? C8 C7 H7B 109.1 . . ? H7A C7 H7B 107.8 . . ? C9 C8 C27 118.0(5) . . ? C9 C8 C7 119.4(5) . . ? C27 C8 C7 122.5(5) . . ? C8 C9 C10 120.4(6) . . ? C8 C9 H9 119.8 . . ? C10 C9 H9 119.8 . . ? C11 C10 C9 120.0(6) . . ? C11 C10 H10 120.0 . . ? C9 C10 H10 120.0 . . ? C10 C11 C12 121.1(5) . . ? C10 C11 H11 119.5 . . ? C12 C11 H11 119.5 . . ? C27 C12 C11 117.4(5) . . ? C27 C12 C13 122.9(5) . . ? C11 C12 C13 119.6(5) . . ? C14 C13 C12 113.2(4) . . ? C14 C13 H13A 108.9 . . ? C12 C13 H13A 108.9 . . ? C14 C13 H13B 108.9 . . ? C12 C13 H13B 108.9 . . ? H13A C13 H13B 107.8 . . ? C15 C14 C26 117.7(5) . . ? C15 C14 C13 121.3(5) . . ? C26 C14 C13 121.0(5) . . ? C14 C15 C16 122.2(5) . . ? C14 C15 H15 118.9 . . ? C16 C15 H15 118.9 . . ? C17 C16 C15 118.1(5) . . ? C17 C16 H16 120.9 . . ? C15 C16 H16 120.9 . . ? C16 C17 C18 123.3(5) . . ? C16 C17 H17 118.4 . . ? C18 C17 H17 118.4 . . ? C17 C18 C26 115.9(5) . . ? C17 C18 C19 120.9(5) . . ? C26 C18 C19 123.2(5) . . ? C18 C19 C20 111.2(4) . . ? C18 C19 H19A 109.4 . . ? C20 C19 H19A 109.4 . . ? C18 C19 H19B 109.4 . . ? C20 C19 H19B 109.4 . . ? H19A C19 H19B 108.0 . . ? C21 C20 C25 118.0(5) . . ? C21 C20 C19 120.7(5) . . ? C25 C20 C19 121.2(5) . . ? C20 C21 C22 120.8(5) . . ? C20 C21 H21 119.6 . . ? C22 C21 H21 119.6 . . ? C23 C22 C21 119.5(6) . . ? C23 C22 H22 120.3 . . ? C21 C22 H22 120.3 . . ? C22 C23 C24 121.5(6) . . ? C22 C23 H23 119.2 . . ? C24 C23 H23 119.2 . . ? C25 C24 C23 117.2(5) . . ? C25 C24 C1 123.2(5) . . ? C23 C24 C1 119.5(6) . . ? C20 C25 C24 122.8(5) . . ? C20 C25 O1 118.1(5) . . ? C24 C25 O1 118.9(5) . . ? O2 C26 C14 116.7(5) . . ? O2 C26 C18 120.7(5) . . ? C14 C26 C18 122.6(5) . . ? C12 C27 C8 122.9(5) . . ? C12 C27 O3 118.8(5) . . ? C8 C27 O3 118.2(5) . . ? O4 C28 C2 116.8(5) . . ? O4 C28 C6 121.2(5) . . ? C2 C28 C6 121.9(5) . . ? O1 C29 C30 109.9(4) . . ? O1 C29 H29A 109.7 . . ? C30 C29 H29A 109.7 . . ? O1 C29 H29B 109.7 . . ? C30 C29 H29B 109.7 . . ? H29A C29 H29B 108.2 . . ? O6 C30 N3 125.1(6) . . ? O6 C30 C29 120.2(6) . . ? N3 C30 C29 114.8(5) . . ? N3 C31 C32 111.0(4) . . ? N3 C31 H31A 109.4 . . ? C32 C31 H31A 109.4 . . ? N3 C31 H31B 109.4 . . ? C32 C31 H31B 109.4 . . ? H31A C31 H31B 108.0 . . ? N2 C32 C31 111.8(5) . . ? N2 C32 H32A 109.3 . . ? C31 C32 H32A 109.3 . . ? N2 C32 H32B 109.3 . . ? C31 C32 H32B 109.3 . . ? H32A C32 H32B 107.9 . . ? N2 C33 C34 112.6(4) . . ? N2 C33 H33A 109.1 . . ? C34 C33 H33A 109.1 . . ? N2 C33 H33B 109.1 . . ? C34 C33 H33B 109.1 . . ? H33A C33 H33B 107.8 . . ? N1 C34 C33 113.4(4) . . ? N1 C34 H34A 108.9 . . ? C33 C34 H34A 108.9 . . ? N1 C34 H34B 108.9 . . ? C33 C34 H34B 108.9 . . ? H34A C34 H34B 107.7 . . ? O5 C35 N1 123.3(6) . . ? O5 C35 C36 120.1(5) . . ? N1 C35 C36 116.6(5) . . ? O3 C36 C35 111.5(4) . . ? O3 C36 H36A 109.3 . . ? C35 C36 H36A 109.3 . . ? O3 C36 H36B 109.3 . . ? C35 C36 H36B 109.3 . . ? H36A C36 H36B 108.0 . . ? C37 O7 H7 109.5 . . ? O7 C37 H37A 109.5 . . ? O7 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? O7 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? 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 C24 C1 C2 C3 107.9(6) . . . . ? C24 C1 C2 C28 -72.6(6) . . . . ? C28 C2 C3 C4 -1.2(8) . . . . ? C1 C2 C3 C4 178.3(5) . . . . ? C2 C3 C4 C5 2.6(9) . . . . ? C3 C4 C5 C6 -1.3(9) . . . . ? C4 C5 C6 C28 -1.5(8) . . . . ? C4 C5 C6 C7 178.9(5) . . . . ? C5 C6 C7 C8 -110.6(6) . . . . ? C28 C6 C7 C8 69.8(7) . . . . ? C6 C7 C8 C9 76.4(6) . . . . ? C6 C7 C8 C27 -102.2(6) . . . . ? C27 C8 C9 C10 1.3(8) . . . . ? C7 C8 C9 C10 -177.4(5) . . . . ? C8 C9 C10 C11 1.2(8) . . . . ? C9 C10 C11 C12 -0.3(8) . . . . ? C10 C11 C12 C27 -3.1(8) . . . . ? C10 C11 C12 C13 176.4(5) . . . . ? C27 C12 C13 C14 105.1(6) . . . . ? C11 C12 C13 C14 -74.4(6) . . . . ? C12 C13 C14 C15 104.1(6) . . . . ? C12 C13 C14 C26 -76.3(6) . . . . ? C26 C14 C15 C16 2.0(8) . . . . ? C13 C14 C15 C16 -178.3(5) . . . . ? C14 C15 C16 C17 0.1(9) . . . . ? C15 C16 C17 C18 -1.0(9) . . . . ? C16 C17 C18 C26 -0.3(8) . . . . ? C16 C17 C18 C19 177.7(5) . . . . ? C17 C18 C19 C20 -103.2(6) . . . . ? C26 C18 C19 C20 74.6(6) . . . . ? C18 C19 C20 C21 73.9(6) . . . . ? C18 C19 C20 C25 -104.5(6) . . . . ? C25 C20 C21 C22 2.4(8) . . . . ? C19 C20 C21 C22 -176.0(5) . . . . ? C20 C21 C22 C23 0.9(9) . . . . ? C21 C22 C23 C24 -1.9(9) . . . . ? C22 C23 C24 C25 -0.4(8) . . . . ? C22 C23 C24 C1 177.0(5) . . . . ? C2 C1 C24 C25 105.8(6) . . . . ? C2 C1 C24 C23 -71.3(6) . . . . ? C21 C20 C25 C24 -4.9(8) . . . . ? C19 C20 C25 C24 173.5(5) . . . . ? C21 C20 C25 O1 179.9(4) . . . . ? C19 C20 C25 O1 -1.6(7) . . . . ? C23 C24 C25 C20 3.9(8) . . . . ? C1 C24 C25 C20 -173.4(5) . . . . ? C23 C24 C25 O1 179.0(4) . . . . ? C1 C24 C25 O1 1.8(7) . . . . ? C29 O1 C25 C20 -98.0(5) . . . . ? C29 O1 C25 C24 86.7(5) . . . . ? C15 C14 C26 O2 176.2(4) . . . . ? C13 C14 C26 O2 -3.4(7) . . . . ? C15 C14 C26 C18 -3.4(8) . . . . ? C13 C14 C26 C18 176.9(5) . . . . ? C17 C18 C26 O2 -177.1(5) . . . . ? C19 C18 C26 O2 5.0(8) . . . . ? C17 C18 C26 C14 2.6(8) . . . . ? C19 C18 C26 C14 -175.3(5) . . . . ? C11 C12 C27 C8 5.7(8) . . . . ? C13 C12 C27 C8 -173.8(5) . . . . ? C11 C12 C27 O3 -177.8(4) . . . . ? C13 C12 C27 O3 2.7(7) . . . . ? C9 C8 C27 C12 -4.8(8) . . . . ? C7 C8 C27 C12 173.7(5) . . . . ? C9 C8 C27 O3 178.7(4) . . . . ? C7 C8 C27 O3 -2.7(7) . . . . ? C36 O3 C27 C12 92.7(5) . . . . ? C36 O3 C27 C8 -90.7(6) . . . . ? C3 C2 C28 O4 175.7(5) . . . . ? C1 C2 C28 O4 -3.8(7) . . . . ? C3 C2 C28 C6 -1.7(8) . . . . ? C1 C2 C28 C6 178.8(5) . . . . ? C5 C6 C28 O4 -174.3(5) . . . . ? C7 C6 C28 O4 5.4(8) . . . . ? C5 C6 C28 C2 3.0(8) . . . . ? C7 C6 C28 C2 -177.4(5) . . . . ? C25 O1 C29 C30 -155.1(5) . . . . ? C31 N3 C30 O6 7.6(9) . . . . ? C31 N3 C30 C29 -173.4(5) . . . . ? O1 C29 C30 O6 -164.8(5) . . . . ? O1 C29 C30 N3 16.2(6) . . . . ? C30 N3 C31 C32 110.6(6) . . . . ? C33 N2 C32 C31 -171.4(4) . . . . ? N3 C31 C32 N2 -64.7(6) . . . . ? C32 N2 C33 C34 -96.3(5) . . . . ? C35 N1 C34 C33 78.9(6) . . . . ? N2 C33 C34 N1 56.1(6) . . . . ? C34 N1 C35 O5 2.7(9) . . . . ? C34 N1 C35 C36 -176.0(5) . . . . ? C27 O3 C36 C35 -143.2(5) . . . . ? O5 C35 C36 O3 -173.3(5) . . . . ? N1 C35 C36 O3 5.5(7) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O4 H4 O3 0.82 2.07 2.846(5) 157.8 . O2 H2 O1 0.82 2.12 2.878(5) 154.0 . O2 H2 O7 0.82 2.42 2.891(6) 117.7 . N3 H3 O4 0.86 2.25 3.100(5) 170.3 . N3 H3 O1 0.86 2.18 2.578(5) 108.1 . N1 H1 O2 0.86 2.34 3.200(5) 174.1 . N1 H1 O3 0.86 2.23 2.638(5) 108.8 . O7 H7 N2 0.82 2.02 2.823(7) 164.3 . N2 H2A O6 0.92(4) 2.14(4) 2.909(6) 140(4) 3_755 data_LHClO4 _database_code_depnum_ccdc_archive 'CCDC 257060' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C36 H38 N3 O6), 2(Cl O4), 5(H2 O)' _chemical_formula_sum 'C72 H86 Cl2 N6 O25' _chemical_formula_weight 1506.37 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 12.7722(18) _cell_length_b 15.865(2) _cell_length_c 20.138(3) _cell_angle_alpha 78.132(2) _cell_angle_beta 71.638(2) _cell_angle_gamma 69.810(2) _cell_volume 3613.3(9) _cell_formula_units_Z 2 _cell_measurement_temperature 298 _cell_measurement_reflns_used 6704 _cell_measurement_theta_min 2.29 _cell_measurement_theta_max 21.98 _exptl_crystal_description 'thin plate' _exptl_crystal_colour yellow _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.385 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1588 _exptl_absorpt_coefficient_mu 0.175 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.864 _exptl_absorpt_correction_T_max 0.993 _exptl_absorpt_process_details 'SADABS-Bruker Nonius area detector scaling and absorption correction - V2.10' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 42510 _diffrn_reflns_av_R_equivalents 0.0443 _diffrn_reflns_av_sigmaI/netI 0.0691 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.65 _diffrn_reflns_theta_max 28.32 _reflns_number_total 16948 _reflns_number_gt 7827 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows/Platon' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1837P)^2^+0.0112P] 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 16948 _refine_ls_number_parameters 970 _refine_ls_number_restraints 10 _refine_ls_R_factor_all 0.1720 _refine_ls_R_factor_gt 0.0910 _refine_ls_wR_factor_ref 0.3236 _refine_ls_wR_factor_gt 0.2634 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.6324(4) 0.7946(3) 1.1308(2) 0.0629(11) Uani 1 1 d . . . H1A H 0.6098 0.8218 1.1742 0.076 Uiso 1 1 calc R . . H1B H 0.5770 0.8286 1.1041 0.076 Uiso 1 1 calc R . . C2 C 0.7513(4) 0.8009(3) 1.0888(2) 0.0610(10) Uani 1 1 d . . . C3 C 0.8219(4) 0.8189(3) 1.1204(3) 0.0737(13) Uani 1 1 d . . . H3 H 0.7962 0.8269 1.1680 0.088 Uiso 1 1 calc R . . C4 C 0.9301(5) 0.8251(3) 1.0822(3) 0.0817(14) Uani 1 1 d . . . H4 H 0.9751 0.8406 1.1033 0.098 Uiso 1 1 calc R . . C5 C 0.9707(4) 0.8084(3) 1.0135(3) 0.0746(13) Uani 1 1 d . . . H5 H 1.0451 0.8101 0.9888 0.089 Uiso 1 1 calc R . . C6 C 0.9038(4) 0.7888(3) 0.9793(2) 0.0641(11) Uani 1 1 d . . . C7 C 0.9550(4) 0.7639(3) 0.9045(2) 0.0689(12) Uani 1 1 d . . . H7A H 0.9020 0.7994 0.8765 0.083 Uiso 1 1 calc R . . H7B H 1.0268 0.7791 0.8845 0.083 Uiso 1 1 calc R . . C8 C 0.9786(3) 0.6647(3) 0.9005(2) 0.0587(10) Uani 1 1 d . . . C9 C 1.0737(4) 0.5996(4) 0.9215(2) 0.0679(12) Uani 1 1 d . . . H9 H 1.1242 0.6182 0.9357 0.081 Uiso 1 1 calc R . . C10 C 1.0921(4) 0.5095(4) 0.9212(2) 0.0673(12) Uani 1 1 d . . . H10 H 1.1553 0.4671 0.9347 0.081 Uiso 1 1 calc R . . C11 C 1.0175(4) 0.4815(3) 0.9009(2) 0.0652(11) Uani 1 1 d . . . H11 H 1.0308 0.4200 0.9014 0.078 Uiso 1 1 calc R . . C12 C 0.9238(3) 0.5414(3) 0.8799(2) 0.0565(10) Uani 1 1 d . . . C13 C 0.8408(4) 0.5079(3) 0.8615(2) 0.0619(11) Uani 1 1 d . . . H13A H 0.8844 0.4643 0.8277 0.074 Uiso 1 1 calc R . . H13B H 0.7900 0.5583 0.8391 0.074 Uiso 1 1 calc R . . C14 C 0.7684(3) 0.4646(3) 0.9241(2) 0.0569(10) Uani 1 1 d . . . C15 C 0.7943(4) 0.3720(3) 0.9378(3) 0.0681(12) Uani 1 1 d . . . H15 H 0.8532 0.3361 0.9054 0.082 Uiso 1 1 calc R . . C16 C 0.7355(4) 0.3311(3) 0.9981(3) 0.0725(13) Uani 1 1 d . . . H16 H 0.7538 0.2685 1.0064 0.087 Uiso 1 1 calc R . . C17 C 0.6488(4) 0.3853(3) 1.0461(3) 0.0722(13) Uani 1 1 d . . . H17 H 0.6105 0.3578 1.0875 0.087 Uiso 1 1 calc R . . C18 C 0.6165(3) 0.4781(3) 1.0352(2) 0.0587(10) Uani 1 1 d . . . C19 C 0.5234(4) 0.5338(3) 1.0903(2) 0.0619(11) Uani 1 1 d . . . H19A H 0.4796 0.4961 1.1229 0.074 Uiso 1 1 calc R . . H19B H 0.4706 0.5821 1.0676 0.074 Uiso 1 1 calc R . . C20 C 0.5728(3) 0.5743(3) 1.13071(19) 0.0548(10) Uani 1 1 d . . . C21 C 0.6283(4) 0.5194(3) 1.1807(2) 0.0660(11) Uani 1 1 d . . . H21 H 0.6290 0.4594 1.1918 0.079 Uiso 1 1 calc R . . C22 C 0.6819(4) 0.5530(3) 1.2139(2) 0.0676(12) Uani 1 1 d . . . H22 H 0.7174 0.5159 1.2478 0.081 Uiso 1 1 calc R . . C23 C 0.6836(4) 0.6404(3) 1.1975(2) 0.0637(11) Uani 1 1 d . . . H23 H 0.7223 0.6613 1.2195 0.076 Uiso 1 1 calc R . . C24 C 0.6286(3) 0.6992(3) 1.14826(19) 0.0579(10) Uani 1 1 d . . . C25 C 0.5725(3) 0.6634(3) 1.11685(19) 0.0560(10) Uani 1 1 d . . . C26 C 0.7929(4) 0.7872(3) 1.0183(2) 0.0570(10) Uani 1 1 d . . . C27 C 0.9070(3) 0.6326(3) 0.87941(18) 0.0546(10) Uani 1 1 d . . . C28 C 0.6754(3) 0.5186(3) 0.9731(2) 0.0537(10) Uani 1 1 d . . . C29 C 0.3965(4) 0.7616(3) 1.0930(2) 0.0671(11) Uani 1 1 d . . . H29A H 0.3821 0.7816 1.1383 0.081 Uiso 1 1 calc R . . H29B H 0.3537 0.7192 1.0994 0.081 Uiso 1 1 calc R . . C30 C 0.3565(4) 0.8419(3) 1.0417(3) 0.0698(12) Uani 1 1 d . . . C31 C 0.4089(5) 0.9615(3) 0.9539(3) 0.0864(15) Uani 1 1 d . . . H31A H 0.4773 0.9816 0.9354 0.104 Uiso 1 1 calc R . . H31B H 0.3512 1.0048 0.9849 0.104 Uiso 1 1 calc R . . C32 C 0.3637(6) 0.9614(3) 0.8944(3) 0.0945(17) Uani 1 1 d . . . H32A H 0.3426 1.0226 0.8715 0.113 Uiso 1 1 calc R . . H32B H 0.2938 0.9434 0.9131 0.113 Uiso 1 1 calc R . . C33 C 0.4277(4) 0.8128(3) 0.8492(3) 0.0678(12) Uani 1 1 d . . . H33A H 0.3530 0.8207 0.8422 0.081 Uiso 1 1 calc R . . H33B H 0.4272 0.7849 0.8969 0.081 Uiso 1 1 calc R . . C34 C 0.5231(4) 0.7506(3) 0.7969(3) 0.0716(12) Uani 1 1 d . . . H34A H 0.5055 0.6947 0.8010 0.086 Uiso 1 1 calc R . . H34B H 0.5260 0.7797 0.7493 0.086 Uiso 1 1 calc R . . C35 C 0.7239(4) 0.7518(3) 0.7629(2) 0.0654(11) Uani 1 1 d . . . C36 C 0.8333(4) 0.7248(3) 0.7853(2) 0.0639(11) Uani 1 1 d . . . H36A H 0.8906 0.6761 0.7594 0.077 Uiso 1 1 calc R . . H36B H 0.8637 0.7757 0.7746 0.077 Uiso 1 1 calc R . . C37 C 0.1759(4) 0.7654(3) 0.2784(2) 0.0667(12) Uani 1 1 d . . . H37A H 0.1820 0.7853 0.2288 0.080 Uiso 1 1 calc R . . H37B H 0.2013 0.8047 0.2967 0.080 Uiso 1 1 calc R . . C38 C 0.0508(4) 0.7722(3) 0.3172(2) 0.0574(10) Uani 1 1 d . . . C39 C -0.0274(5) 0.7769(3) 0.2813(3) 0.0776(14) Uani 1 1 d . . . H39 H -0.0039 0.7792 0.2325 0.093 Uiso 1 1 calc R . . C40 C -0.1399(5) 0.7783(4) 0.3165(3) 0.0863(16) Uani 1 1 d . . . H40 H -0.1917 0.7817 0.2916 0.104 Uiso 1 1 calc R . . C41 C -0.1745(4) 0.7746(3) 0.3882(3) 0.0671(12) Uani 1 1 d . . . H41 H -0.2506 0.7765 0.4117 0.081 Uiso 1 1 calc R . . C42 C -0.0996(3) 0.7683(2) 0.4268(2) 0.0520(9) Uani 1 1 d . . . C43 C -0.1411(3) 0.7622(3) 0.5056(2) 0.0582(10) Uani 1 1 d . . . H43A H -0.2250 0.7787 0.5193 0.070 Uiso 1 1 calc R . . H43B H -0.1194 0.8058 0.5216 0.070 Uiso 1 1 calc R . . C44 C -0.0935(3) 0.6689(3) 0.5427(2) 0.0535(9) Uani 1 1 d . . . C45 C -0.1413(4) 0.6005(3) 0.5496(2) 0.0624(11) Uani 1 1 d . . . H45 H -0.2051 0.6118 0.5325 0.075 Uiso 1 1 calc R . . C46 C -0.0958(4) 0.5160(3) 0.5814(2) 0.0674(12) Uani 1 1 d . . . H46 H -0.1298 0.4711 0.5864 0.081 Uiso 1 1 calc R . . C47 C -0.0003(4) 0.4974(3) 0.6059(2) 0.0633(11) Uani 1 1 d . . . H47 H 0.0305 0.4395 0.6265 0.076 Uiso 1 1 calc R . . C48 C 0.0517(3) 0.5646(3) 0.60037(19) 0.0530(9) Uani 1 1 d . . . C49 C 0.1613(4) 0.5409(3) 0.6237(2) 0.0576(10) Uani 1 1 d . . . H49A H 0.1752 0.5962 0.6268 0.069 Uiso 1 1 calc R . . H49B H 0.1508 0.5077 0.6702 0.069 Uiso 1 1 calc R . . C50 C 0.2652(3) 0.4850(3) 0.5739(2) 0.0514(9) Uani 1 1 d . . . C51 C 0.3078(4) 0.3924(3) 0.5889(2) 0.0636(11) Uani 1 1 d . . . H51 H 0.2739 0.3641 0.6315 0.076 Uiso 1 1 calc R . . C52 C 0.4007(4) 0.3411(3) 0.5410(3) 0.0727(13) Uani 1 1 d . . . H52 H 0.4291 0.2790 0.5519 0.087 Uiso 1 1 calc R . . C53 C 0.4501(4) 0.3814(3) 0.4780(3) 0.0641(11) Uani 1 1 d . . . H53 H 0.5108 0.3463 0.4458 0.077 Uiso 1 1 calc R . . C54 C 0.4111(3) 0.4741(3) 0.4612(2) 0.0541(10) Uani 1 1 d . . . C55 C 0.4685(3) 0.5187(3) 0.3922(2) 0.0621(11) Uani 1 1 d . . . H55A H 0.5411 0.4760 0.3707 0.075 Uiso 1 1 calc R . . H55B H 0.4855 0.5697 0.4010 0.075 Uiso 1 1 calc R . . C56 C 0.3914(3) 0.5513(3) 0.3412(2) 0.0561(10) Uani 1 1 d . . . C57 C 0.3791(4) 0.4871(3) 0.3077(2) 0.0690(12) Uani 1 1 d . . . H57 H 0.4196 0.4263 0.3151 0.083 Uiso 1 1 calc R . . C58 C 0.3077(4) 0.5141(4) 0.2643(2) 0.0768(13) Uani 1 1 d . . . H58 H 0.3014 0.4716 0.2414 0.092 Uiso 1 1 calc R . . C59 C 0.2446(4) 0.6036(4) 0.2540(2) 0.0709(12) Uani 1 1 d . . . H59 H 0.1958 0.6202 0.2246 0.085 Uiso 1 1 calc R . . C60 C 0.2526(4) 0.6697(3) 0.2868(2) 0.0589(10) Uani 1 1 d . . . C61 C 0.3309(3) 0.6409(3) 0.32776(19) 0.0544(10) Uani 1 1 d . . . C62 C 0.0131(3) 0.7695(2) 0.3898(2) 0.0502(9) Uani 1 1 d . . . C63 C 0.0004(3) 0.6492(3) 0.57019(19) 0.0492(9) Uani 1 1 d . . . C64 C 0.3189(3) 0.5249(2) 0.5099(2) 0.0483(9) Uani 1 1 d . . . C65 C 0.4420(4) 0.7368(3) 0.3220(2) 0.0594(10) Uani 1 1 d . . . H65A H 0.4481 0.7438 0.2720 0.071 Uiso 1 1 calc R . . H65B H 0.5120 0.6917 0.3302 0.071 Uiso 1 1 calc R . . C66 C 0.4324(4) 0.8249(3) 0.3431(2) 0.0598(10) Uani 1 1 d . . . C67 C 0.3034(5) 0.9671(4) 0.3850(3) 0.0899(16) Uani 1 1 d . . . H67A H 0.2305 1.0021 0.3744 0.108 Uiso 1 1 calc R . . H67B H 0.3635 0.9903 0.3519 0.108 Uiso 1 1 calc R . . C68 C 0.2968(5) 0.9802(4) 0.4584(3) 0.0937(17) Uani 1 1 d . . . H68A H 0.3652 0.9391 0.4716 0.112 Uiso 1 1 calc R . . H68B H 0.2961 1.0413 0.4589 0.112 Uiso 1 1 calc R . . C69 C 0.1706(4) 0.9913(3) 0.5823(3) 0.0728(13) Uani 1 1 d . . . H69A H 0.2275 0.9496 0.6057 0.087 Uiso 1 1 calc R . . H69B H 0.1777 1.0513 0.5778 0.087 Uiso 1 1 calc R . . C70 C 0.0517(5) 0.9906(3) 0.6256(2) 0.0725(13) Uani 1 1 d . . . H70A H 0.0353 1.0144 0.6697 0.087 Uiso 1 1 calc R . . H70B H -0.0043 1.0299 0.6008 0.087 Uiso 1 1 calc R . . C71 C 0.0081(3) 0.8645(3) 0.5983(2) 0.0517(9) Uani 1 1 d . . . C72 C -0.0033(3) 0.7723(3) 0.62307(19) 0.0539(9) Uani 1 1 d . . . H72A H 0.0361 0.7442 0.6597 0.065 Uiso 1 1 calc R . . H72B H -0.0843 0.7756 0.6423 0.065 Uiso 1 1 calc R . . N1 N 0.4386(4) 0.8738(3) 0.9951(2) 0.0732(10) Uani 1 1 d . . . H1 H 0.5101 0.8421 0.9893 0.088 Uiso 1 1 calc R . . N2 N 0.4460(4) 0.9007(3) 0.8402(2) 0.0802(11) Uani 1 1 d D . . H2A H 0.441(5) 0.926(4) 0.795(2) 0.120 Uiso 1 1 d D . . H2B H 0.526(4) 0.897(4) 0.836(3) 0.120 Uiso 1 1 d D . . N3 N 0.6336(3) 0.7311(2) 0.81020(18) 0.0652(9) Uani 1 1 d . . . H3A H 0.6421 0.7047 0.8508 0.078 Uiso 1 1 calc R . . N4 N 0.3279(3) 0.8728(3) 0.3755(2) 0.0739(10) Uani 1 1 d . . . H4B H 0.2733 0.8481 0.3912 0.089 Uiso 1 1 calc R . . N5 N 0.1941(3) 0.9642(3) 0.5101(2) 0.0714(10) Uani 1 1 d D . . H5A H 0.211(5) 0.904(2) 0.510(3) 0.107 Uiso 1 1 d D . . H5B H 0.127(4) 0.988(3) 0.493(3) 0.107 Uiso 1 1 d D . . N6 N 0.0387(3) 0.9001(2) 0.64053(18) 0.0629(9) Uani 1 1 d . . . H6 H 0.0517 0.8682 0.6788 0.075 Uiso 1 1 calc R . . O1 O 0.5176(2) 0.71833(19) 1.06615(13) 0.0588(7) Uani 1 1 d . . . O2 O 0.7181(2) 0.7729(2) 0.98866(15) 0.0680(8) Uani 1 1 d . . . H2 H 0.7498 0.7655 0.9471 0.102 Uiso 1 1 calc R . . O3 O 0.8122(2) 0.6961(2) 0.85893(13) 0.0605(7) Uani 1 1 d . . . O4 O 0.6482(2) 0.60910(19) 0.95555(14) 0.0616(7) Uani 1 1 d . . . H4A H 0.5935 0.6344 0.9865 0.092 Uiso 1 1 calc R . . O5 O 0.2532(3) 0.8745(2) 1.0463(2) 0.0975(11) Uani 1 1 d . . . O6 O 0.7214(3) 0.7887(3) 0.70390(16) 0.0897(11) Uani 1 1 d . . . O7 O 0.3439(2) 0.70594(19) 0.36057(13) 0.0558(7) Uani 1 1 d . . . O8 O 0.0925(2) 0.77006(19) 0.42201(13) 0.0593(7) Uani 1 1 d . . . H8 H 0.0639 0.7685 0.4647 0.089 Uiso 1 1 calc R . . O9 O 0.0476(2) 0.71992(16) 0.56391(12) 0.0475(6) Uani 1 1 d . . . O10 O 0.2770(2) 0.61666(16) 0.49700(13) 0.0547(6) Uani 1 1 d . . . H10A H 0.3140 0.6336 0.4583 0.082 Uiso 1 1 calc R . . O11 O 0.5188(3) 0.8486(2) 0.32604(19) 0.0800(9) Uani 1 1 d . . . O12 O -0.0125(3) 0.90563(19) 0.54302(15) 0.0640(7) Uani 1 1 d . . . Cl1 Cl 0.29949(15) 0.01473(11) 0.18723(8) 0.0953(5) Uani 1 1 d . . . O13 O 0.1922(5) 0.0315(4) 0.2331(3) 0.166(2) Uani 1 1 d . . . O14 O 0.3908(7) -0.0260(8) 0.2158(4) 0.288(6) Uani 1 1 d . . . O15 O 0.3236(5) 0.0972(4) 0.1538(4) 0.168(2) Uani 1 1 d . . . O16 O 0.3091(10) -0.0315(10) 0.1402(7) 0.357(9) Uani 1 1 d . . . Cl2 Cl 0.74085(16) 0.25625(11) 0.26969(9) 0.1016(5) Uani 1 1 d . . . O17 O 0.7056(6) 0.2875(4) 0.2078(3) 0.169(3) Uani 1 1 d . . . O18 O 0.6905(11) 0.1972(8) 0.3140(6) 0.294(6) Uani 1 1 d . . . O19 O 0.8482(7) 0.2078(7) 0.2542(3) 0.279(6) Uani 1 1 d . . . O20 O 0.7393(12) 0.3203(6) 0.3039(5) 0.278(6) Uani 1 1 d . . . O21 O 0.8189(6) 0.0233(6) 0.2164(5) 0.219(3) Uani 1 1 d . . . O22 O 0.6026(4) 0.9987(3) 0.2828(3) 0.1177(15) Uani 1 1 d D . . H22A H 0.673(5) 1.010(6) 0.270(5) 0.177 Uiso 1 1 d D . . H22B H 0.599(8) 0.950(4) 0.271(5) 0.177 Uiso 1 1 d D . . O23 O 0.0546(5) 0.9692(5) 0.1483(4) 0.194(3) Uani 1 1 d . . . O24 O 0.2682(4) 0.7777(2) 0.5421(2) 0.0959(12) Uani 1 1 d D . . H24B H 0.253(6) 0.733(4) 0.531(4) 0.144 Uiso 1 1 d D . . H24A H 0.288(7) 0.747(5) 0.574(3) 0.144 Uiso 1 1 d D . . O25 O 0.4603(16) 0.1361(16) 0.3953(8) 0.458(13) 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 C1 0.062(3) 0.069(3) 0.051(2) -0.0186(19) -0.013(2) -0.005(2) C2 0.064(3) 0.059(2) 0.058(2) -0.0077(19) -0.022(2) -0.009(2) C3 0.078(3) 0.078(3) 0.064(3) -0.017(2) -0.033(3) -0.004(3) C4 0.075(3) 0.082(3) 0.102(4) -0.017(3) -0.050(3) -0.015(3) C5 0.060(3) 0.088(3) 0.082(3) -0.016(3) -0.024(2) -0.022(2) C6 0.062(3) 0.064(3) 0.068(3) -0.006(2) -0.018(2) -0.020(2) C7 0.061(3) 0.085(3) 0.063(3) -0.003(2) -0.014(2) -0.031(2) C8 0.045(2) 0.084(3) 0.046(2) -0.010(2) -0.0017(17) -0.026(2) C9 0.042(2) 0.100(4) 0.064(3) -0.017(2) -0.011(2) -0.023(2) C10 0.042(2) 0.092(4) 0.065(3) -0.015(2) -0.015(2) -0.012(2) C11 0.050(2) 0.081(3) 0.062(3) -0.016(2) -0.014(2) -0.013(2) C12 0.044(2) 0.078(3) 0.045(2) -0.0117(19) -0.0068(17) -0.017(2) C13 0.054(2) 0.081(3) 0.053(2) -0.022(2) -0.0163(19) -0.012(2) C14 0.049(2) 0.067(3) 0.062(2) -0.012(2) -0.026(2) -0.015(2) C15 0.056(3) 0.075(3) 0.085(3) -0.023(3) -0.031(2) -0.016(2) C16 0.064(3) 0.062(3) 0.097(4) -0.002(3) -0.040(3) -0.015(2) C17 0.070(3) 0.077(3) 0.080(3) 0.010(3) -0.034(3) -0.034(3) C18 0.049(2) 0.065(3) 0.067(3) -0.002(2) -0.021(2) -0.019(2) C19 0.051(2) 0.071(3) 0.061(2) 0.000(2) -0.013(2) -0.022(2) C20 0.045(2) 0.069(3) 0.045(2) 0.0010(18) -0.0081(17) -0.0176(19) C21 0.056(3) 0.073(3) 0.056(2) 0.007(2) -0.010(2) -0.016(2) C22 0.060(3) 0.084(3) 0.046(2) 0.003(2) -0.017(2) -0.011(2) C23 0.052(2) 0.086(3) 0.045(2) -0.010(2) -0.0117(18) -0.011(2) C24 0.046(2) 0.072(3) 0.042(2) -0.0116(19) -0.0052(17) -0.0045(19) C25 0.044(2) 0.070(3) 0.042(2) -0.0031(18) -0.0104(17) -0.0045(19) C26 0.057(2) 0.061(2) 0.054(2) -0.0101(19) -0.021(2) -0.012(2) C27 0.040(2) 0.080(3) 0.0370(19) -0.0065(18) -0.0047(16) -0.0152(19) C28 0.042(2) 0.072(3) 0.051(2) -0.0067(19) -0.0171(18) -0.0187(19) C29 0.050(2) 0.075(3) 0.070(3) -0.006(2) -0.017(2) -0.011(2) C30 0.063(3) 0.065(3) 0.080(3) -0.019(2) -0.031(3) -0.001(2) C31 0.107(4) 0.072(3) 0.075(3) -0.010(3) -0.032(3) -0.013(3) C32 0.119(5) 0.065(3) 0.086(4) -0.003(3) -0.046(3) 0.004(3) C33 0.063(3) 0.062(3) 0.079(3) 0.004(2) -0.023(2) -0.021(2) C34 0.062(3) 0.087(3) 0.072(3) -0.011(2) -0.023(2) -0.025(2) C35 0.065(3) 0.079(3) 0.044(2) -0.006(2) -0.012(2) -0.015(2) C36 0.053(2) 0.088(3) 0.043(2) -0.005(2) -0.0076(18) -0.018(2) C37 0.085(3) 0.082(3) 0.042(2) 0.003(2) -0.022(2) -0.038(3) C38 0.068(3) 0.053(2) 0.053(2) 0.0034(18) -0.025(2) -0.017(2) C39 0.099(4) 0.094(3) 0.060(3) 0.008(2) -0.041(3) -0.044(3) C40 0.102(4) 0.107(4) 0.080(3) 0.017(3) -0.060(3) -0.053(3) C41 0.065(3) 0.061(3) 0.089(3) 0.010(2) -0.040(2) -0.028(2) C42 0.054(2) 0.0392(19) 0.065(2) 0.0033(17) -0.0265(19) -0.0119(17) C43 0.040(2) 0.060(2) 0.072(3) -0.009(2) -0.0177(19) -0.0085(18) C44 0.045(2) 0.058(2) 0.053(2) -0.0017(18) -0.0103(17) -0.0154(18) C45 0.049(2) 0.076(3) 0.068(3) -0.001(2) -0.019(2) -0.027(2) C46 0.060(3) 0.073(3) 0.080(3) 0.004(2) -0.022(2) -0.037(2) C47 0.062(3) 0.058(2) 0.068(3) 0.005(2) -0.015(2) -0.025(2) C48 0.051(2) 0.062(2) 0.046(2) -0.0007(17) -0.0150(17) -0.0182(19) C49 0.064(3) 0.065(2) 0.049(2) 0.0077(18) -0.0254(19) -0.024(2) C50 0.051(2) 0.054(2) 0.060(2) 0.0007(18) -0.0296(19) -0.0206(18) C51 0.063(3) 0.062(3) 0.077(3) 0.013(2) -0.040(2) -0.025(2) C52 0.067(3) 0.046(2) 0.116(4) -0.003(3) -0.053(3) -0.008(2) C53 0.049(2) 0.057(3) 0.092(3) -0.013(2) -0.032(2) -0.008(2) C54 0.043(2) 0.055(2) 0.074(3) -0.009(2) -0.028(2) -0.0140(18) C55 0.044(2) 0.073(3) 0.068(3) -0.017(2) -0.0111(19) -0.014(2) C56 0.046(2) 0.071(3) 0.051(2) -0.0149(19) -0.0061(18) -0.020(2) C57 0.062(3) 0.074(3) 0.073(3) -0.022(2) -0.012(2) -0.020(2) C58 0.084(3) 0.091(4) 0.069(3) -0.031(3) -0.014(3) -0.036(3) C59 0.082(3) 0.090(4) 0.056(3) -0.014(2) -0.028(2) -0.032(3) C60 0.066(3) 0.071(3) 0.043(2) -0.0055(19) -0.0129(19) -0.026(2) C61 0.055(2) 0.072(3) 0.041(2) -0.0152(18) -0.0043(17) -0.029(2) C62 0.056(2) 0.041(2) 0.058(2) -0.0009(16) -0.0268(19) -0.0118(17) C63 0.043(2) 0.058(2) 0.047(2) -0.0015(17) -0.0113(16) -0.0191(17) C64 0.048(2) 0.049(2) 0.058(2) -0.0025(17) -0.0254(18) -0.0186(17) C65 0.055(2) 0.073(3) 0.051(2) -0.014(2) -0.0021(19) -0.028(2) C66 0.060(3) 0.061(3) 0.058(2) -0.005(2) -0.020(2) -0.015(2) C67 0.083(4) 0.073(3) 0.094(4) -0.022(3) 0.005(3) -0.018(3) C68 0.072(3) 0.074(3) 0.135(5) -0.037(3) -0.006(3) -0.027(3) C69 0.085(3) 0.045(2) 0.100(4) -0.016(2) -0.044(3) -0.013(2) C70 0.093(4) 0.054(3) 0.071(3) -0.016(2) -0.035(3) -0.006(2) C71 0.047(2) 0.055(2) 0.047(2) -0.0103(18) -0.0130(17) -0.0042(17) C72 0.051(2) 0.070(3) 0.0404(19) -0.0060(18) -0.0103(17) -0.0198(19) N1 0.073(3) 0.067(2) 0.074(2) -0.0016(19) -0.028(2) -0.010(2) N2 0.092(3) 0.068(3) 0.082(3) 0.001(2) -0.037(3) -0.018(2) N3 0.054(2) 0.082(2) 0.056(2) -0.0009(17) -0.0200(17) -0.0155(18) N4 0.067(2) 0.073(3) 0.076(2) -0.022(2) -0.004(2) -0.021(2) N5 0.066(2) 0.062(2) 0.087(3) -0.016(2) -0.026(2) -0.011(2) N6 0.075(2) 0.059(2) 0.056(2) -0.0152(16) -0.0247(18) -0.0103(17) O1 0.0459(15) 0.0745(18) 0.0463(14) -0.0021(13) -0.0133(12) -0.0076(13) O2 0.0567(17) 0.100(2) 0.0522(16) -0.0145(15) -0.0109(13) -0.0291(16) O3 0.0480(15) 0.086(2) 0.0414(14) -0.0020(13) -0.0118(12) -0.0158(14) O4 0.0574(17) 0.0624(18) 0.0544(16) -0.0047(13) -0.0063(13) -0.0138(14) O5 0.066(2) 0.092(3) 0.129(3) -0.020(2) -0.043(2) 0.0026(19) O6 0.073(2) 0.135(3) 0.0529(19) 0.0099(19) -0.0215(16) -0.028(2) O7 0.0504(15) 0.0745(18) 0.0461(14) -0.0163(13) -0.0028(12) -0.0267(13) O8 0.0487(15) 0.087(2) 0.0466(14) -0.0102(13) -0.0155(12) -0.0216(14) O9 0.0455(14) 0.0538(15) 0.0435(13) -0.0083(11) -0.0078(11) -0.0174(12) O10 0.0588(16) 0.0454(15) 0.0531(15) -0.0040(11) -0.0088(12) -0.0137(12) O11 0.066(2) 0.068(2) 0.111(3) -0.0072(17) -0.0168(18) -0.0333(17) O12 0.076(2) 0.0617(17) 0.0611(17) 0.0002(14) -0.0346(15) -0.0186(15) Cl1 0.1010(11) 0.0873(10) 0.0942(10) -0.0140(8) -0.0245(9) -0.0232(8) O13 0.102(4) 0.182(5) 0.163(5) -0.035(4) 0.028(4) -0.027(3) O14 0.148(6) 0.413(14) 0.162(6) 0.100(8) -0.039(5) 0.010(7) O15 0.133(4) 0.124(4) 0.229(7) 0.008(4) -0.046(4) -0.035(3) O16 0.274(11) 0.488(18) 0.393(15) -0.339(15) 0.093(11) -0.214(12) Cl2 0.1144(12) 0.0818(9) 0.1200(12) 0.0043(9) -0.0723(10) -0.0154(9) O17 0.240(6) 0.127(4) 0.213(6) 0.043(4) -0.183(6) -0.067(4) O18 0.345(13) 0.319(12) 0.310(11) 0.167(10) -0.190(11) -0.234(11) O19 0.173(6) 0.400(13) 0.117(5) -0.005(6) -0.071(5) 0.108(8) O20 0.489(17) 0.177(7) 0.265(10) -0.043(6) -0.233(11) -0.091(8) O21 0.122(5) 0.224(7) 0.321(10) -0.107(7) -0.026(5) -0.047(5) O22 0.121(4) 0.103(3) 0.139(4) 0.029(3) -0.056(3) -0.050(3) O23 0.127(4) 0.230(7) 0.222(7) -0.063(6) 0.013(4) -0.083(5) O24 0.095(3) 0.069(2) 0.126(3) -0.029(2) -0.038(2) -0.010(2) O25 0.45(2) 0.69(3) 0.283(14) -0.170(17) 0.133(14) -0.37(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C24 1.495(6) . ? C1 C2 1.514(6) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 C3 1.383(6) . ? C2 C26 1.385(6) . ? C3 C4 1.380(7) . ? C3 H3 0.9300 . ? C4 C5 1.363(7) . ? C4 H4 0.9300 . ? C5 C6 1.394(6) . ? C5 H5 0.9300 . ? C6 C26 1.393(6) . ? C6 C7 1.515(6) . ? C7 C8 1.512(6) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C27 1.389(6) . ? C8 C9 1.414(6) . ? C9 C10 1.368(7) . ? C9 H9 0.9300 . ? C10 C11 1.374(6) . ? C10 H10 0.9300 . ? C11 C12 1.372(6) . ? C11 H11 0.9300 . ? C12 C27 1.386(6) . ? C12 C13 1.504(6) . ? C13 C14 1.505(6) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C15 1.378(6) . ? C14 C28 1.423(6) . ? C15 C16 1.378(7) . ? C15 H15 0.9300 . ? C16 C17 1.382(7) . ? C16 H16 0.9300 . ? C17 C18 1.375(6) . ? C17 H17 0.9300 . ? C18 C28 1.398(6) . ? C18 C19 1.507(6) . ? C19 C20 1.514(6) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 C25 1.382(6) . ? C20 C21 1.392(6) . ? C21 C22 1.374(6) . ? C21 H21 0.9300 . ? C22 C23 1.363(6) . ? C22 H22 0.9300 . ? C23 C24 1.397(6) . ? C23 H23 0.9300 . ? C24 C25 1.397(6) . ? C25 O1 1.399(4) . ? C26 O2 1.373(5) . ? C27 O3 1.398(5) . ? C28 O4 1.354(5) . ? C29 O1 1.432(5) . ? C29 C30 1.514(6) . ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? C30 O5 1.220(5) . ? C30 N1 1.337(6) . ? C31 N1 1.458(6) . ? C31 C32 1.487(7) . ? C31 H31A 0.9700 . ? C31 H31B 0.9700 . ? C32 N2 1.494(7) . ? C32 H32A 0.9700 . ? C32 H32B 0.9700 . ? C33 N2 1.458(6) . ? C33 C34 1.536(7) . ? C33 H33A 0.9700 . ? C33 H33B 0.9700 . ? C34 N3 1.436(5) . ? C34 H34A 0.9700 . ? C34 H34B 0.9700 . ? C35 O6 1.217(5) . ? C35 N3 1.335(5) . ? C35 C36 1.498(6) . ? C36 O3 1.426(4) . ? C36 H36A 0.9700 . ? C36 H36B 0.9700 . ? C37 C60 1.506(6) . ? C37 C38 1.518(6) . ? C37 H37A 0.9700 . ? C37 H37B 0.9700 . ? C38 C39 1.380(6) . ? C38 C62 1.385(5) . ? C39 C40 1.382(7) . ? C39 H39 0.9300 . ? C40 C41 1.366(7) . ? C40 H40 0.9300 . ? C41 C42 1.376(5) . ? C41 H41 0.9300 . ? C42 C62 1.402(6) . ? C42 C43 1.501(6) . ? C43 C44 1.526(5) . ? C43 H43A 0.9700 . ? C43 H43B 0.9700 . ? C44 C45 1.383(6) . ? C44 C63 1.389(5) . ? C45 C46 1.375(6) . ? C45 H45 0.9300 . ? C46 C47 1.375(6) . ? C46 H46 0.9300 . ? C47 C48 1.408(6) . ? C47 H47 0.9300 . ? C48 C63 1.382(5) . ? C48 C49 1.516(5) . ? C49 C50 1.506(6) . ? C49 H49A 0.9700 . ? C49 H49B 0.9700 . ? C50 C51 1.385(6) . ? C50 C64 1.392(5) . ? C51 C52 1.392(7) . ? C51 H51 0.9300 . ? C52 C53 1.363(7) . ? C52 H52 0.9300 . ? C53 C54 1.386(6) . ? C53 H53 0.9300 . ? C54 C64 1.393(6) . ? C54 C55 1.509(6) . ? C55 C56 1.536(6) . ? C55 H55A 0.9700 . ? C55 H55B 0.9700 . ? C56 C61 1.380(6) . ? C56 C57 1.406(6) . ? C57 C58 1.362(6) . ? C57 H57 0.9300 . ? C58 C59 1.379(7) . ? C58 H58 0.9300 . ? C59 C60 1.395(6) . ? C59 H59 0.9300 . ? C60 C61 1.393(5) . ? C61 O7 1.414(5) . ? C62 O8 1.368(4) . ? C63 O9 1.414(4) . ? C64 O10 1.367(4) . ? C65 O7 1.438(4) . ? C65 C66 1.498(6) . ? C65 H65A 0.9700 . ? C65 H65B 0.9700 . ? C66 O11 1.213(5) . ? C66 N4 1.319(5) . ? C67 N4 1.460(6) . ? C67 C68 1.506(8) . ? C67 H67A 0.9700 . ? C67 H67B 0.9700 . ? C68 N5 1.459(7) . ? C68 H68A 0.9700 . ? C68 H68B 0.9700 . ? C69 C70 1.497(7) . ? C69 N5 1.511(6) . ? C69 H69A 0.9700 . ? C69 H69B 0.9700 . ? C70 N6 1.461(6) . ? C70 H70A 0.9700 . ? C70 H70B 0.9700 . ? C71 O12 1.225(4) . ? C71 N6 1.325(5) . ? C71 C72 1.486(6) . ? C72 O9 1.442(4) . ? C72 H72A 0.9700 . ? C72 H72B 0.9700 . ? N1 H1 0.8600 . ? N2 H2A 0.93(4) . ? N2 H2B 0.98(4) . ? N3 H3A 0.8600 . ? N4 H4B 0.8600 . ? N5 H5A 0.91(4) . ? N5 H5B 0.96(4) . ? N6 H6 0.8600 . ? O2 H2 0.8200 . ? O4 H4A 0.8200 . ? O8 H8 0.8200 . ? O10 H10A 0.8200 . ? Cl1 O16 1.266(8) . ? Cl1 O13 1.362(5) . ? Cl1 O14 1.363(8) . ? Cl1 O15 1.429(6) . ? Cl2 O19 1.292(7) . ? Cl2 O20 1.331(7) . ? Cl2 O18 1.341(8) . ? Cl2 O17 1.396(5) . ? O22 H22A 0.92(4) . ? O22 H22B 0.87(4) . ? O24 H24B 0.89(4) . ? O24 H24A 0.77(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C24 C1 C2 112.5(3) . . ? C24 C1 H1A 109.1 . . ? C2 C1 H1A 109.1 . . ? C24 C1 H1B 109.1 . . ? C2 C1 H1B 109.1 . . ? H1A C1 H1B 107.8 . . ? C3 C2 C26 118.4(4) . . ? C3 C2 C1 120.7(4) . . ? C26 C2 C1 120.9(4) . . ? C4 C3 C2 120.9(4) . . ? C4 C3 H3 119.6 . . ? C2 C3 H3 119.6 . . ? C5 C4 C3 119.7(4) . . ? C5 C4 H4 120.2 . . ? C3 C4 H4 120.2 . . ? C4 C5 C6 121.8(5) . . ? C4 C5 H5 119.1 . . ? C6 C5 H5 119.1 . . ? C26 C6 C5 117.1(4) . . ? C26 C6 C7 122.5(4) . . ? C5 C6 C7 120.2(4) . . ? C8 C7 C6 112.5(4) . . ? C8 C7 H7A 109.1 . . ? C6 C7 H7A 109.1 . . ? C8 C7 H7B 109.1 . . ? C6 C7 H7B 109.1 . . ? H7A C7 H7B 107.8 . . ? C27 C8 C9 117.0(4) . . ? C27 C8 C7 122.6(4) . . ? C9 C8 C7 120.3(4) . . ? C10 C9 C8 120.5(4) . . ? C10 C9 H9 119.8 . . ? C8 C9 H9 119.8 . . ? C9 C10 C11 120.0(4) . . ? C9 C10 H10 120.0 . . ? C11 C10 H10 120.0 . . ? C12 C11 C10 122.1(5) . . ? C12 C11 H11 118.9 . . ? C10 C11 H11 118.9 . . ? C11 C12 C27 117.3(4) . . ? C11 C12 C13 120.5(4) . . ? C27 C12 C13 122.2(4) . . ? C12 C13 C14 113.4(3) . . ? C12 C13 H13A 108.9 . . ? C14 C13 H13A 108.9 . . ? C12 C13 H13B 108.9 . . ? C14 C13 H13B 108.9 . . ? H13A C13 H13B 107.7 . . ? C15 C14 C28 118.3(4) . . ? C15 C14 C13 121.1(4) . . ? C28 C14 C13 120.5(4) . . ? C14 C15 C16 122.0(5) . . ? C14 C15 H15 119.0 . . ? C16 C15 H15 119.0 . . ? C15 C16 C17 118.4(4) . . ? C15 C16 H16 120.8 . . ? C17 C16 H16 120.8 . . ? C18 C17 C16 122.9(5) . . ? C18 C17 H17 118.6 . . ? C16 C17 H17 118.6 . . ? C17 C18 C28 118.0(4) . . ? C17 C18 C19 120.6(4) . . ? C28 C18 C19 121.4(4) . . ? C18 C19 C20 112.1(3) . . ? C18 C19 H19A 109.2 . . ? C20 C19 H19A 109.2 . . ? C18 C19 H19B 109.2 . . ? C20 C19 H19B 109.2 . . ? H19A C19 H19B 107.9 . . ? C25 C20 C21 117.5(4) . . ? C25 C20 C19 122.6(4) . . ? C21 C20 C19 119.7(4) . . ? C22 C21 C20 120.7(4) . . ? C22 C21 H21 119.7 . . ? C20 C21 H21 119.7 . . ? C23 C22 C21 120.5(4) . . ? C23 C22 H22 119.7 . . ? C21 C22 H22 119.7 . . ? C22 C23 C24 121.6(4) . . ? C22 C23 H23 119.2 . . ? C24 C23 H23 119.2 . . ? C25 C24 C23 116.3(4) . . ? C25 C24 C1 123.2(4) . . ? C23 C24 C1 120.5(4) . . ? C20 C25 C24 123.3(4) . . ? C20 C25 O1 117.5(4) . . ? C24 C25 O1 119.1(4) . . ? O2 C26 C2 116.2(4) . . ? O2 C26 C6 121.8(4) . . ? C2 C26 C6 122.0(4) . . ? C12 C27 C8 123.0(4) . . ? C12 C27 O3 119.3(3) . . ? C8 C27 O3 117.7(4) . . ? O4 C28 C18 123.2(4) . . ? O4 C28 C14 116.4(3) . . ? C18 C28 C14 120.4(4) . . ? O1 C29 C30 109.4(4) . . ? O1 C29 H29A 109.8 . . ? C30 C29 H29A 109.8 . . ? O1 C29 H29B 109.8 . . ? C30 C29 H29B 109.8 . . ? H29A C29 H29B 108.3 . . ? O5 C30 N1 124.4(5) . . ? O5 C30 C29 119.0(5) . . ? N1 C30 C29 116.6(4) . . ? N1 C31 C32 114.1(4) . . ? N1 C31 H31A 108.7 . . ? C32 C31 H31A 108.7 . . ? N1 C31 H31B 108.7 . . ? C32 C31 H31B 108.7 . . ? H31A C31 H31B 107.6 . . ? C31 C32 N2 114.9(5) . . ? C31 C32 H32A 108.6 . . ? N2 C32 H32A 108.6 . . ? C31 C32 H32B 108.6 . . ? N2 C32 H32B 108.6 . . ? H32A C32 H32B 107.5 . . ? N2 C33 C34 111.0(4) . . ? N2 C33 H33A 109.4 . . ? C34 C33 H33A 109.4 . . ? N2 C33 H33B 109.4 . . ? C34 C33 H33B 109.4 . . ? H33A C33 H33B 108.0 . . ? N3 C34 C33 110.7(4) . . ? N3 C34 H34A 109.5 . . ? C33 C34 H34A 109.5 . . ? N3 C34 H34B 109.5 . . ? C33 C34 H34B 109.5 . . ? H34A C34 H34B 108.1 . . ? O6 C35 N3 123.6(4) . . ? O6 C35 C36 120.0(4) . . ? N3 C35 C36 116.4(4) . . ? O3 C36 C35 110.5(3) . . ? O3 C36 H36A 109.6 . . ? C35 C36 H36A 109.6 . . ? O3 C36 H36B 109.6 . . ? C35 C36 H36B 109.6 . . ? H36A C36 H36B 108.1 . . ? C60 C37 C38 110.7(3) . . ? C60 C37 H37A 109.5 . . ? C38 C37 H37A 109.5 . . ? C60 C37 H37B 109.5 . . ? C38 C37 H37B 109.5 . . ? H37A C37 H37B 108.1 . . ? C39 C38 C62 118.0(4) . . ? C39 C38 C37 120.9(4) . . ? C62 C38 C37 121.0(3) . . ? C38 C39 C40 121.4(4) . . ? C38 C39 H39 119.3 . . ? C40 C39 H39 119.3 . . ? C41 C40 C39 119.4(4) . . ? C41 C40 H40 120.3 . . ? C39 C40 H40 120.3 . . ? C40 C41 C42 121.7(4) . . ? C40 C41 H41 119.1 . . ? C42 C41 H41 119.1 . . ? C41 C42 C62 117.8(4) . . ? C41 C42 C43 119.6(4) . . ? C62 C42 C43 122.6(3) . . ? C42 C43 C44 114.2(3) . . ? C42 C43 H43A 108.7 . . ? C44 C43 H43A 108.7 . . ? C42 C43 H43B 108.7 . . ? C44 C43 H43B 108.7 . . ? H43A C43 H43B 107.6 . . ? C45 C44 C63 117.5(4) . . ? C45 C44 C43 121.3(4) . . ? C63 C44 C43 121.2(4) . . ? C46 C45 C44 120.8(4) . . ? C46 C45 H45 119.6 . . ? C44 C45 H45 119.6 . . ? C47 C46 C45 120.6(4) . . ? C47 C46 H46 119.7 . . ? C45 C46 H46 119.7 . . ? C46 C47 C48 120.9(4) . . ? C46 C47 H47 119.5 . . ? C48 C47 H47 119.5 . . ? C63 C48 C47 116.3(4) . . ? C63 C48 C49 123.7(4) . . ? C47 C48 C49 119.9(4) . . ? C50 C49 C48 112.3(3) . . ? C50 C49 H49A 109.1 . . ? C48 C49 H49A 109.1 . . ? C50 C49 H49B 109.1 . . ? C48 C49 H49B 109.1 . . ? H49A C49 H49B 107.9 . . ? C51 C50 C64 117.9(4) . . ? C51 C50 C49 121.4(4) . . ? C64 C50 C49 120.7(3) . . ? C50 C51 C52 120.7(4) . . ? C50 C51 H51 119.6 . . ? C52 C51 H51 119.6 . . ? C53 C52 C51 120.3(4) . . ? C53 C52 H52 119.9 . . ? C51 C52 H52 119.9 . . ? C52 C53 C54 120.9(4) . . ? C52 C53 H53 119.5 . . ? C54 C53 H53 119.5 . . ? C53 C54 C64 118.3(4) . . ? C53 C54 C55 120.6(4) . . ? C64 C54 C55 121.1(4) . . ? C54 C55 C56 111.8(3) . . ? C54 C55 H55A 109.3 . . ? C56 C55 H55A 109.3 . . ? C54 C55 H55B 109.3 . . ? C56 C55 H55B 109.3 . . ? H55A C55 H55B 107.9 . . ? C61 C56 C57 118.0(4) . . ? C61 C56 C55 123.1(4) . . ? C57 C56 C55 118.8(4) . . ? C58 C57 C56 119.9(5) . . ? C58 C57 H57 120.1 . . ? C56 C57 H57 120.1 . . ? C57 C58 C59 121.0(4) . . ? C57 C58 H58 119.5 . . ? C59 C58 H58 119.5 . . ? C58 C59 C60 121.4(4) . . ? C58 C59 H59 119.3 . . ? C60 C59 H59 119.3 . . ? C61 C60 C59 116.4(4) . . ? C61 C60 C37 123.9(4) . . ? C59 C60 C37 119.7(4) . . ? C56 C61 C60 123.2(4) . . ? C56 C61 O7 118.4(3) . . ? C60 C61 O7 118.3(4) . . ? O8 C62 C38 115.3(4) . . ? O8 C62 C42 123.1(3) . . ? C38 C62 C42 121.6(4) . . ? C48 C63 C44 123.7(4) . . ? C48 C63 O9 119.0(3) . . ? C44 C63 O9 117.2(3) . . ? O10 C64 C50 116.8(3) . . ? O10 C64 C54 121.3(3) . . ? C50 C64 C54 121.9(4) . . ? O7 C65 C66 111.8(3) . . ? O7 C65 H65A 109.3 . . ? C66 C65 H65A 109.3 . . ? O7 C65 H65B 109.3 . . ? C66 C65 H65B 109.3 . . ? H65A C65 H65B 107.9 . . ? O11 C66 N4 125.4(4) . . ? O11 C66 C65 118.1(4) . . ? N4 C66 C65 116.4(4) . . ? N4 C67 C68 113.2(5) . . ? N4 C67 H67A 108.9 . . ? C68 C67 H67A 108.9 . . ? N4 C67 H67B 108.9 . . ? C68 C67 H67B 108.9 . . ? H67A C67 H67B 107.7 . . ? N5 C68 C67 112.5(4) . . ? N5 C68 H68A 109.1 . . ? C67 C68 H68A 109.1 . . ? N5 C68 H68B 109.1 . . ? C67 C68 H68B 109.1 . . ? H68A C68 H68B 107.8 . . ? C70 C69 N5 110.5(4) . . ? C70 C69 H69A 109.6 . . ? N5 C69 H69A 109.6 . . ? C70 C69 H69B 109.6 . . ? N5 C69 H69B 109.6 . . ? H69A C69 H69B 108.1 . . ? N6 C70 C69 112.5(4) . . ? N6 C70 H70A 109.1 . . ? C69 C70 H70A 109.1 . . ? N6 C70 H70B 109.1 . . ? C69 C70 H70B 109.1 . . ? H70A C70 H70B 107.8 . . ? O12 C71 N6 122.3(4) . . ? O12 C71 C72 121.9(4) . . ? N6 C71 C72 115.8(3) . . ? O9 C72 C71 108.2(3) . . ? O9 C72 H72A 110.1 . . ? C71 C72 H72A 110.1 . . ? O9 C72 H72B 110.1 . . ? C71 C72 H72B 110.1 . . ? H72A C72 H72B 108.4 . . ? C30 N1 C31 121.0(4) . . ? C30 N1 H1 119.5 . . ? C31 N1 H1 119.5 . . ? C33 N2 C32 114.1(4) . . ? C33 N2 H2A 106(4) . . ? C32 N2 H2A 112(4) . . ? C33 N2 H2B 113(4) . . ? C32 N2 H2B 111(4) . . ? H2A N2 H2B 100(4) . . ? C35 N3 C34 123.5(4) . . ? C35 N3 H3A 118.2 . . ? C34 N3 H3A 118.2 . . ? C66 N4 C67 121.1(4) . . ? C66 N4 H4B 119.4 . . ? C67 N4 H4B 119.4 . . ? C68 N5 C69 115.4(4) . . ? C68 N5 H5A 100(4) . . ? C69 N5 H5A 113(4) . . ? C68 N5 H5B 113(3) . . ? C69 N5 H5B 112(3) . . ? H5A N5 H5B 103(4) . . ? C71 N6 C70 123.5(4) . . ? C71 N6 H6 118.2 . . ? C70 N6 H6 118.2 . . ? C25 O1 C29 114.5(3) . . ? C26 O2 H2 109.5 . . ? C27 O3 C36 114.7(3) . . ? C28 O4 H4A 109.5 . . ? C61 O7 C65 113.0(3) . . ? C62 O8 H8 109.5 . . ? C63 O9 C72 113.6(3) . . ? C64 O10 H10A 109.5 . . ? O16 Cl1 O13 111.3(5) . . ? O16 Cl1 O14 108.2(8) . . ? O13 Cl1 O14 116.4(4) . . ? O16 Cl1 O15 108.6(8) . . ? O13 Cl1 O15 110.9(4) . . ? O14 Cl1 O15 100.7(6) . . ? O19 Cl2 O20 103.8(8) . . ? O19 Cl2 O18 101.5(7) . . ? O20 Cl2 O18 110.9(8) . . ? O19 Cl2 O17 108.9(4) . . ? O20 Cl2 O17 115.1(4) . . ? O18 Cl2 O17 115.1(5) . . ? H22A O22 H22B 120(9) . . ? H24B O24 H24A 91(7) . . ? _diffrn_measured_fraction_theta_max 0.942 _diffrn_reflns_theta_full 28.32 _diffrn_measured_fraction_theta_full 0.942 _refine_diff_density_max 0.802 _refine_diff_density_min -0.510 _refine_diff_density_rms 0.077