# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Wang, Chun-Jiang' _publ_contact_author_email cjwang@whu.edu.cn _publ_section_title ; Stereoselective Construction of 5-aza-Spiro[2,4] heptane Motif via Catalytic Asymmetric 1,3-Dipolar Cycloaddition of Azomethine Ylides and Ethyl Cyclopropylidene Acetate ; loop_ _publ_author_name 'Tang-Lin Liu' 'zhao-lin He' 'Hai-Yan Tao' 'Yue-Peng Cai' ; Chun-Jiang Wang ; # Attachment '- cif.cif' data_c _database_code_depnum_ccdc_archive 'CCDC 785673' #TrackingRef '- cif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H20 Cl N O4' _chemical_formula_sum 'C17 H20 Cl N O4' _chemical_formula_weight 337.79 _chemical_absolute_configuration rm 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 P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.479(2) _cell_length_b 27.837(6) _cell_length_c 13.143(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.399(3) _cell_angle_gamma 90.00 _cell_volume 3467.8(13) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 4006 _cell_measurement_theta_min 2.27 _cell_measurement_theta_max 21.84 _exptl_crystal_description block _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.294 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1424 _exptl_absorpt_coefficient_mu 0.239 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9405 _exptl_absorpt_correction_T_max 0.9650 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18013 _diffrn_reflns_av_R_equivalents 0.0288 _diffrn_reflns_av_sigmaI/netI 0.0529 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -33 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.71 _diffrn_reflns_theta_max 25.25 _reflns_number_total 11687 _reflns_number_gt 7093 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _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^)+(0.0701P)^2^+0.1372P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0049(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.11(7) _refine_ls_number_reflns 11687 _refine_ls_number_parameters 838 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0944 _refine_ls_R_factor_gt 0.0514 _refine_ls_wR_factor_ref 0.1506 _refine_ls_wR_factor_gt 0.1253 _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_restrained_S_all 1.020 _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 0.34305(14) 0.96020(5) 0.37934(13) 0.1051(5) Uani 1 1 d . . . Cl2 Cl 0.32467(15) 0.96237(5) 0.84946(12) 0.1028(5) Uani 1 1 d . . . Cl3 Cl 1.16724(14) -0.00483(5) 1.13111(13) 0.1091(5) Uani 1 1 d . . . Cl4 Cl 1.16257(13) -0.00392(5) 0.60006(11) 0.0970(4) Uani 1 1 d . . . O1 O 0.8306(5) 0.79921(14) 0.2150(3) 0.1281(16) Uani 1 1 d . . . O2 O 0.7762(4) 0.82339(13) 0.0619(3) 0.1113(14) Uani 1 1 d . . . O3 O 1.1489(4) 0.78874(14) 0.3622(2) 0.0914(10) Uani 1 1 d . . . O4 O 1.3461(4) 0.82469(13) 0.3113(3) 0.1007(11) Uani 1 1 d . . . O5 O 0.8025(6) 0.82369(16) 0.5507(3) 0.145(2) Uani 1 1 d . . . O6 O 0.7967(4) 0.81009(11) 0.7143(2) 0.0813(9) Uani 1 1 d . . . O7 O 1.0322(4) 0.77461(11) 0.8660(2) 0.0849(9) Uani 1 1 d . . . O8 O 1.2585(4) 0.78305(12) 0.8284(2) 0.0868(9) Uani 1 1 d . . . O9 O 0.6813(5) 0.15541(14) 0.9702(3) 0.1222(15) Uani 1 1 d . . . O10 O 0.7257(4) 0.13354(14) 0.8148(3) 0.1168(14) Uani 1 1 d . . . O11 O 0.3583(4) 0.16673(14) 1.1124(2) 0.0921(11) Uani 1 1 d . . . O12 O 0.1596(4) 0.13021(13) 1.0613(3) 0.1010(11) Uani 1 1 d . . . O13 O 0.6745(5) 0.13273(16) 0.2977(3) 0.1245(15) Uani 1 1 d . . . O14 O 0.6856(3) 0.14819(10) 0.4611(2) 0.0756(8) Uani 1 1 d . . . O15 O 0.4541(3) 0.18369(11) 0.6145(2) 0.0800(9) Uani 1 1 d . . . O16 O 0.2258(3) 0.17393(11) 0.5800(2) 0.0822(9) Uani 1 1 d . . . N1 N 1.0060(4) 0.87569(13) 0.3237(2) 0.0680(9) Uani 1 1 d . . . H1 H 0.9845 0.8699 0.3860 0.082 Uiso 1 1 calc R . . N2 N 0.9847(4) 0.87098(12) 0.8384(2) 0.0645(9) Uani 1 1 d . . . H2 H 0.9547 0.8674 0.8995 0.077 Uiso 1 1 calc R . . N3 N 0.4994(4) 0.07917(12) 1.0751(2) 0.0690(10) Uani 1 1 d . . . H3 H 0.5208 0.0844 1.1379 0.083 Uiso 1 1 calc R . . N4 N 0.5037(3) 0.08755(12) 0.5890(2) 0.0600(9) Uani 1 1 d . . . H4 H 0.5358 0.0916 0.6498 0.072 Uiso 1 1 calc R . . C1 C 0.5078(5) 0.93978(18) 0.3377(4) 0.0796(13) Uani 1 1 d . . . C2 C 0.5576(5) 0.95565(18) 0.2463(4) 0.0808(13) Uani 1 1 d . . . H2A H 0.5039 0.9758 0.2049 0.097 Uiso 1 1 calc R . . C3 C 0.6900(5) 0.94075(18) 0.2178(3) 0.0780(13) Uani 1 1 d . . . H3A H 0.7252 0.9511 0.1557 0.094 Uiso 1 1 calc R . . C4 C 0.7728(5) 0.91114(14) 0.2773(3) 0.0629(11) Uani 1 1 d . . . C5 C 0.7171(6) 0.89581(19) 0.3672(4) 0.0804(13) Uani 1 1 d . . . H5 H 0.7696 0.8754 0.4088 0.096 Uiso 1 1 calc R . . C6 C 0.5824(6) 0.91024(18) 0.3977(4) 0.0865(14) Uani 1 1 d . . . H6 H 0.5452 0.8994 0.4589 0.104 Uiso 1 1 calc R . . C7 C 0.9212(4) 0.90012(15) 0.2470(3) 0.0610(10) Uani 1 1 d . . . H7 H 0.9670 0.9311 0.2346 0.073 Uiso 1 1 calc R . . C8 C 0.9414(5) 0.86979(14) 0.1489(3) 0.0660(11) Uani 1 1 d . . . H8 H 0.9270 0.8895 0.0879 0.079 Uiso 1 1 calc R . . C9 C 0.8436(5) 0.82699(16) 0.1482(3) 0.0709(13) Uani 1 1 d . . . C10 C 0.6905(9) 0.7788(3) 0.0470(6) 0.164(4) Uani 1 1 d . . . H10A H 0.7125 0.7646 -0.0184 0.197 Uiso 1 1 calc R . . H10B H 0.7145 0.7556 0.0995 0.197 Uiso 1 1 calc R . . C11 C 0.5603(9) 0.7880(4) 0.0507(10) 0.246(6) Uani 1 1 d . . . H11A H 0.5393 0.8034 0.1142 0.369 Uiso 1 1 calc R . . H11B H 0.5076 0.7586 0.0452 0.369 Uiso 1 1 calc R . . H11C H 0.5351 0.8089 -0.0045 0.369 Uiso 1 1 calc R . . C12 C 1.0949(5) 0.85453(14) 0.1591(3) 0.0649(11) Uani 1 1 d . . . C13 C 1.1982(6) 0.86412(18) 0.0759(4) 0.0892(15) Uani 1 1 d . . . H13A H 1.1629 0.8788 0.0138 0.107 Uiso 1 1 calc R . . H13B H 1.2931 0.8736 0.0954 0.107 Uiso 1 1 calc R . . C14 C 1.1534(6) 0.8138(2) 0.0988(4) 0.0923(16) Uani 1 1 d . . . H14A H 1.0912 0.7980 0.0504 0.111 Uiso 1 1 calc R . . H14B H 1.2213 0.7928 0.1320 0.111 Uiso 1 1 calc R . . C15 C 1.1356(5) 0.86324(15) 0.2711(3) 0.0645(11) Uani 1 1 d . . . H15 H 1.1996 0.8909 0.2743 0.077 Uiso 1 1 calc R . . C16 C 1.2071(6) 0.82117(19) 0.3208(3) 0.0724(12) Uani 1 1 d . . . C17 C 1.4301(6) 0.7859(2) 0.3542(6) 0.138(3) Uani 1 1 d . . . H17A H 1.4117 0.7833 0.4257 0.207 Uiso 1 1 calc R . . H17B H 1.5284 0.7925 0.3440 0.207 Uiso 1 1 calc R . . H17C H 1.4056 0.7563 0.3211 0.207 Uiso 1 1 calc R . . C18 C 0.4958(5) 0.94310(15) 0.8221(4) 0.0725(12) Uani 1 1 d . . . C19 C 0.5565(6) 0.95537(17) 0.7333(4) 0.0831(14) Uani 1 1 d . . . H19 H 0.5068 0.9738 0.6862 0.100 Uiso 1 1 calc R . . C20 C 0.6924(6) 0.94058(18) 0.7124(3) 0.0812(13) Uani 1 1 d . . . H20 H 0.7335 0.9488 0.6508 0.097 Uiso 1 1 calc R . . C21 C 0.7672(5) 0.91388(13) 0.7818(3) 0.0630(11) Uani 1 1 d . . . C22 C 0.7036(6) 0.90218(18) 0.8717(3) 0.0778(13) Uani 1 1 d . . . H22 H 0.7527 0.8841 0.9198 0.093 Uiso 1 1 calc R . . C23 C 0.5677(6) 0.91685(17) 0.8917(4) 0.0808(13) Uani 1 1 d . . . H23 H 0.5256 0.9087 0.9530 0.097 Uiso 1 1 calc R . . C24 C 0.9197(5) 0.90002(14) 0.7592(3) 0.0623(11) Uani 1 1 d . . . H24 H 0.9739 0.9299 0.7548 0.075 Uiso 1 1 calc R . . C25 C 0.9446(5) 0.87190(15) 0.6584(3) 0.0702(12) Uani 1 1 d . . . H25 H 0.9489 0.8947 0.6017 0.084 Uiso 1 1 calc R . . C26 C 0.8404(6) 0.83360(17) 0.6338(3) 0.0789(14) Uani 1 1 d . . . C27 C 0.7039(7) 0.7698(2) 0.6991(4) 0.1078(19) Uani 1 1 d . . . H27A H 0.7327 0.7523 0.6388 0.129 Uiso 1 1 calc R . . H27B H 0.7118 0.7482 0.7568 0.129 Uiso 1 1 calc R . . C28 C 0.5601(7) 0.7846(4) 0.6874(8) 0.185(4) Uani 1 1 d . . . H28A H 0.5348 0.8052 0.7431 0.277 Uiso 1 1 calc R . . H28B H 0.5000 0.7569 0.6868 0.277 Uiso 1 1 calc R . . H28C H 0.5492 0.8018 0.6245 0.277 Uiso 1 1 calc R . . C29 C 1.0909(5) 0.85139(15) 0.6781(3) 0.0722(12) Uani 1 1 d . . . C30 C 1.1581(6) 0.8160(2) 0.6067(4) 0.1007(18) Uani 1 1 d . . . H30A H 1.2160 0.7908 0.6362 0.121 Uiso 1 1 calc R . . H30B H 1.1048 0.8065 0.5467 0.121 Uiso 1 1 calc R . . C31 C 1.2124(7) 0.86516(19) 0.6107(4) 0.1059(19) Uani 1 1 d . . . H31A H 1.1925 0.8860 0.5532 0.127 Uiso 1 1 calc R . . H31B H 1.3037 0.8702 0.6428 0.127 Uiso 1 1 calc R . . C32 C 1.1100(5) 0.84903(14) 0.7953(3) 0.0634(11) Uani 1 1 d . . . H32 H 1.1933 0.8677 0.8153 0.076 Uiso 1 1 calc R . . C33 C 1.1251(6) 0.79871(16) 0.8334(3) 0.0664(12) Uani 1 1 d . . . C34 C 1.2825(6) 0.73407(18) 0.8624(5) 0.1015(17) Uani 1 1 d . . . H34A H 1.2493 0.7305 0.9309 0.152 Uiso 1 1 calc R . . H34B H 1.3817 0.7271 0.8603 0.152 Uiso 1 1 calc R . . H34C H 1.2326 0.7123 0.8186 0.152 Uiso 1 1 calc R . . C35 C 1.0019(5) 0.01521(17) 1.0900(4) 0.0800(13) Uani 1 1 d . . . C36 C 0.9237(6) 0.0436(2) 1.1528(4) 0.0900(15) Uani 1 1 d . . . H36 H 0.9601 0.0532 1.2155 0.108 Uiso 1 1 calc R . . C37 C 0.7899(5) 0.05797(18) 1.1228(4) 0.0786(13) Uani 1 1 d . . . H37 H 0.7371 0.0775 1.1656 0.094 Uiso 1 1 calc R . . C38 C 0.7334(5) 0.04373(15) 1.0300(3) 0.0669(11) Uani 1 1 d . . . C39 C 0.8179(5) 0.01550(17) 0.9686(4) 0.0802(13) Uani 1 1 d . . . H39 H 0.7838 0.0061 0.9052 0.096 Uiso 1 1 calc R . . C40 C 0.9506(5) 0.00094(18) 0.9983(4) 0.0841(14) Uani 1 1 d . . . H40 H 1.0045 -0.0185 0.9561 0.101 Uiso 1 1 calc R . . C41 C 0.5849(5) 0.05525(15) 0.9978(3) 0.0645(11) Uani 1 1 d . . . H41 H 0.5388 0.0244 0.9837 0.077 Uiso 1 1 calc R . . C42 C 0.5653(5) 0.08627(15) 0.9007(3) 0.0685(12) Uani 1 1 d . . . H42 H 0.5797 0.0670 0.8393 0.082 Uiso 1 1 calc R . . C43 C 0.6625(5) 0.12849(16) 0.9025(3) 0.0718(13) Uani 1 1 d . . . C44 C 0.8132(10) 0.1786(3) 0.8021(7) 0.165(3) Uani 1 1 d . . . H44A H 0.7924 0.1932 0.7368 0.198 Uiso 1 1 calc R . . H44B H 0.7901 0.2014 0.8551 0.198 Uiso 1 1 calc R . . C45 C 0.9421(10) 0.1680(4) 0.8073(11) 0.246(7) Uani 1 1 d . . . H45A H 0.9593 0.1490 0.8670 0.370 Uiso 1 1 calc R . . H45B H 0.9970 0.1969 0.8109 0.370 Uiso 1 1 calc R . . H45C H 0.9682 0.1501 0.7480 0.370 Uiso 1 1 calc R . . C46 C 0.4120(5) 0.10194(14) 0.9092(3) 0.0654(11) Uani 1 1 d . . . C47 C 0.3076(6) 0.09306(19) 0.8254(3) 0.0885(15) Uani 1 1 d . . . H47A H 0.2129 0.0835 0.8443 0.106 Uiso 1 1 calc R . . H47B H 0.3419 0.0788 0.7630 0.106 Uiso 1 1 calc R . . C48 C 0.3530(6) 0.14332(18) 0.8500(3) 0.0884(15) Uani 1 1 d . . . H48A H 0.4148 0.1594 0.8024 0.106 Uiso 1 1 calc R . . H48B H 0.2857 0.1641 0.8837 0.106 Uiso 1 1 calc R . . C49 C 0.3706(5) 0.09208(16) 1.0217(3) 0.0651(11) Uani 1 1 d . . . H49 H 0.3058 0.0647 1.0234 0.078 Uiso 1 1 calc R . . C50 C 0.3007(6) 0.13449(19) 1.0721(3) 0.0744(13) Uani 1 1 d . . . C51 C 0.0789(7) 0.1695(2) 1.1064(5) 0.142(3) Uani 1 1 d . . . H51A H 0.1056 0.1732 1.1765 0.213 Uiso 1 1 calc R . . H51B H -0.0201 0.1624 1.1018 0.213 Uiso 1 1 calc R . . H51C H 0.0981 0.1988 1.0704 0.213 Uiso 1 1 calc R . . C52 C 0.9927(5) 0.01512(15) 0.5712(4) 0.0666(11) Uani 1 1 d . . . C53 C 0.9224(5) 0.04276(16) 0.6410(3) 0.0758(13) Uani 1 1 d . . . H53 H 0.9667 0.0516 0.7016 0.091 Uiso 1 1 calc R . . C54 C 0.7857(5) 0.05746(17) 0.6210(3) 0.0707(12) Uani 1 1 d . . . H54 H 0.7387 0.0762 0.6685 0.085 Uiso 1 1 calc R . . C55 C 0.7178(4) 0.04479(13) 0.5319(3) 0.0594(10) Uani 1 1 d . . . C56 C 0.7906(5) 0.01671(16) 0.4632(3) 0.0743(13) Uani 1 1 d . . . H56 H 0.7468 0.0075 0.4027 0.089 Uiso 1 1 calc R . . C57 C 0.9279(5) 0.00206(17) 0.4830(3) 0.0747(12) Uani 1 1 d . . . H57 H 0.9756 -0.0167 0.4359 0.090 Uiso 1 1 calc R . . C58 C 0.5675(4) 0.05815(14) 0.5090(3) 0.0591(10) Uani 1 1 d . . . H58 H 0.5137 0.0281 0.5058 0.071 Uiso 1 1 calc R . . C59 C 0.5378(5) 0.08534(14) 0.4084(3) 0.0649(12) Uani 1 1 d . . . H59 H 0.5322 0.0623 0.3521 0.078 Uiso 1 1 calc R . . C60 C 0.6408(5) 0.12352(16) 0.3832(3) 0.0685(12) Uani 1 1 d . . . C61 C 0.7811(6) 0.18736(18) 0.4439(4) 0.0915(15) Uani 1 1 d . . . H61A H 0.7764 0.2095 0.5009 0.110 Uiso 1 1 calc R . . H61B H 0.7519 0.2046 0.3832 0.110 Uiso 1 1 calc R . . C62 C 0.9260(7) 0.1713(3) 0.4320(6) 0.154(3) Uani 1 1 d . . . H62A H 0.9470 0.1471 0.4818 0.230 Uiso 1 1 calc R . . H62B H 0.9887 0.1981 0.4412 0.230 Uiso 1 1 calc R . . H62C H 0.9379 0.1583 0.3650 0.230 Uiso 1 1 calc R . . C63 C 0.3908(5) 0.10595(14) 0.4288(3) 0.0629(11) Uani 1 1 d . . . C64 C 0.2666(6) 0.0912(2) 0.3635(4) 0.0992(18) Uani 1 1 d . . . H64A H 0.2844 0.0701 0.3064 0.119 Uiso 1 1 calc R . . H64B H 0.1766 0.0864 0.3967 0.119 Uiso 1 1 calc R . . C65 C 0.3230(6) 0.14095(19) 0.3585(4) 0.0910(16) Uani 1 1 d . . . H65A H 0.2669 0.1664 0.3882 0.109 Uiso 1 1 calc R . . H65B H 0.3745 0.1501 0.2980 0.109 Uiso 1 1 calc R . . C66 C 0.3756(4) 0.10856(14) 0.5460(3) 0.0572(10) Uani 1 1 d . . . H66 H 0.2937 0.0896 0.5670 0.069 Uiso 1 1 calc R . . C67 C 0.3606(5) 0.15939(16) 0.5838(3) 0.0615(11) Uani 1 1 d . . . C68 C 0.2017(6) 0.22322(18) 0.6116(4) 0.1000(17) Uani 1 1 d . . . H68A H 0.2369 0.2277 0.6796 0.150 Uiso 1 1 calc R . . H68B H 0.1023 0.2299 0.6097 0.150 Uiso 1 1 calc R . . H68C H 0.2498 0.2446 0.5663 0.150 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 Cl1 0.0747(9) 0.0970(10) 0.1437(12) -0.0387(9) 0.0001(8) -0.0057(7) Cl2 0.0908(9) 0.0805(9) 0.1370(12) -0.0053(8) -0.0030(8) 0.0050(7) Cl3 0.0803(9) 0.0977(10) 0.1494(13) 0.0362(10) 0.0015(8) -0.0070(8) Cl4 0.0792(8) 0.0781(8) 0.1335(12) 0.0077(8) 0.0021(8) 0.0080(7) O1 0.196(4) 0.098(3) 0.090(2) 0.042(2) -0.047(3) -0.074(3) O2 0.150(3) 0.092(3) 0.091(2) 0.021(2) -0.052(2) -0.051(2) O3 0.108(3) 0.094(3) 0.072(2) 0.0168(19) 0.0009(19) 0.007(2) O4 0.086(3) 0.091(3) 0.124(3) 0.018(2) -0.013(2) 0.008(2) O5 0.240(5) 0.131(4) 0.065(2) 0.014(2) -0.039(3) -0.071(4) O6 0.120(3) 0.0641(19) 0.0600(18) 0.0051(15) -0.0095(17) -0.0236(18) O7 0.094(2) 0.067(2) 0.094(2) 0.0226(17) 0.0037(19) -0.0053(18) O8 0.094(3) 0.075(2) 0.092(2) 0.0170(17) 0.0161(18) 0.0150(19) O9 0.191(4) 0.091(3) 0.085(2) -0.040(2) 0.041(2) -0.073(3) O10 0.158(4) 0.104(3) 0.089(2) -0.022(2) 0.056(2) -0.054(3) O11 0.113(3) 0.092(3) 0.071(2) -0.0213(19) 0.0009(19) 0.006(2) O12 0.093(3) 0.097(3) 0.114(3) -0.011(2) 0.018(2) 0.012(2) O13 0.184(4) 0.136(3) 0.055(2) -0.005(2) 0.036(2) -0.048(3) O14 0.109(2) 0.0621(18) 0.0560(17) -0.0045(14) 0.0122(16) -0.0187(17) O15 0.086(2) 0.066(2) 0.088(2) -0.0202(17) 0.0069(17) -0.0104(18) O16 0.086(2) 0.070(2) 0.091(2) -0.0144(17) -0.0051(17) 0.0150(17) N1 0.074(2) 0.085(2) 0.0455(17) -0.0026(18) -0.0073(17) 0.0078(19) N2 0.086(3) 0.065(2) 0.0430(16) -0.0031(16) 0.0056(17) 0.0071(18) N3 0.086(3) 0.077(2) 0.0439(17) 0.0042(17) 0.0148(18) 0.0059(19) N4 0.075(2) 0.066(2) 0.0396(16) 0.0026(15) 0.0044(15) 0.0063(17) C1 0.071(3) 0.064(3) 0.104(4) -0.015(3) -0.004(3) -0.010(2) C2 0.083(4) 0.072(3) 0.087(3) 0.004(3) -0.020(3) 0.006(3) C3 0.088(3) 0.075(3) 0.070(3) 0.015(2) -0.005(3) -0.001(3) C4 0.073(3) 0.050(2) 0.066(3) 0.003(2) -0.005(2) -0.007(2) C5 0.081(3) 0.081(3) 0.079(3) 0.015(3) 0.006(3) 0.007(3) C6 0.092(4) 0.078(3) 0.090(3) 0.016(3) 0.008(3) -0.011(3) C7 0.076(3) 0.053(2) 0.054(2) 0.0051(19) -0.001(2) -0.007(2) C8 0.089(3) 0.050(2) 0.058(2) 0.0151(19) -0.009(2) -0.011(2) C9 0.103(4) 0.057(3) 0.053(3) 0.006(2) -0.011(2) -0.010(2) C10 0.184(8) 0.127(6) 0.180(7) 0.026(5) -0.085(7) -0.053(6) C11 0.124(7) 0.207(11) 0.407(19) 0.053(11) -0.018(10) -0.041(8) C12 0.085(3) 0.050(2) 0.059(2) 0.0019(19) 0.003(2) -0.002(2) C13 0.105(4) 0.087(4) 0.075(3) 0.012(3) 0.022(3) 0.007(3) C14 0.126(4) 0.090(4) 0.061(3) -0.011(3) 0.001(3) 0.018(3) C15 0.071(3) 0.061(3) 0.062(2) -0.004(2) -0.004(2) -0.005(2) C16 0.080(4) 0.076(3) 0.062(3) -0.005(2) -0.008(2) 0.002(3) C17 0.101(5) 0.124(5) 0.188(7) 0.040(5) -0.039(4) 0.033(4) C18 0.080(3) 0.047(2) 0.090(3) -0.003(2) -0.005(3) 0.000(2) C19 0.097(4) 0.071(3) 0.081(3) 0.022(3) -0.004(3) 0.008(3) C20 0.109(4) 0.071(3) 0.063(3) 0.015(2) 0.002(3) 0.002(3) C21 0.098(3) 0.040(2) 0.052(2) 0.0036(18) -0.005(2) -0.004(2) C22 0.098(4) 0.073(3) 0.063(3) 0.012(2) 0.001(3) 0.019(3) C23 0.099(4) 0.069(3) 0.074(3) 0.010(2) 0.007(3) 0.010(3) C24 0.093(3) 0.042(2) 0.052(2) 0.0013(18) 0.002(2) -0.008(2) C25 0.119(4) 0.048(2) 0.044(2) 0.0092(18) 0.009(2) -0.002(3) C26 0.125(4) 0.064(3) 0.047(3) 0.002(2) -0.001(3) -0.008(3) C27 0.141(5) 0.079(4) 0.104(4) 0.002(3) -0.013(4) -0.036(4) C28 0.099(6) 0.201(9) 0.254(11) -0.007(8) -0.002(6) -0.034(6) C29 0.110(4) 0.047(2) 0.060(3) 0.008(2) 0.018(2) -0.001(2) C30 0.160(5) 0.078(4) 0.065(3) -0.002(3) 0.027(3) 0.032(3) C31 0.148(5) 0.076(4) 0.094(4) 0.009(3) 0.053(4) 0.006(3) C32 0.086(3) 0.044(2) 0.060(2) -0.0006(19) 0.000(2) -0.006(2) C33 0.087(4) 0.059(3) 0.053(2) 0.000(2) 0.001(2) -0.006(3) C34 0.119(4) 0.071(4) 0.114(4) 0.016(3) 0.006(3) 0.029(3) C35 0.078(3) 0.062(3) 0.101(4) 0.008(3) 0.008(3) -0.014(2) C36 0.096(4) 0.088(4) 0.087(3) -0.013(3) -0.001(3) -0.013(3) C37 0.090(4) 0.069(3) 0.077(3) -0.015(2) 0.000(3) -0.003(3) C38 0.079(3) 0.055(3) 0.066(3) -0.004(2) 0.012(2) -0.006(2) C39 0.094(4) 0.075(3) 0.072(3) -0.014(2) 0.008(3) 0.005(3) C40 0.085(4) 0.072(3) 0.096(4) -0.005(3) 0.022(3) 0.005(3) C41 0.082(3) 0.054(3) 0.057(2) -0.0025(19) 0.010(2) -0.008(2) C42 0.105(4) 0.054(3) 0.046(2) -0.0089(19) 0.011(2) -0.012(2) C43 0.104(4) 0.057(3) 0.055(3) -0.006(2) 0.018(2) -0.015(3) C44 0.200(9) 0.120(6) 0.177(7) -0.018(5) 0.079(7) -0.064(7) C45 0.133(7) 0.186(10) 0.42(2) -0.068(11) 0.056(10) -0.035(8) C46 0.085(3) 0.053(3) 0.058(2) -0.0009(19) 0.011(2) -0.008(2) C47 0.114(4) 0.085(4) 0.066(3) -0.003(3) -0.008(3) 0.010(3) C48 0.133(5) 0.072(3) 0.061(3) 0.010(2) 0.008(3) 0.013(3) C49 0.071(3) 0.067(3) 0.057(2) 0.010(2) 0.007(2) -0.003(2) C50 0.091(4) 0.074(3) 0.059(3) 0.006(2) 0.015(3) 0.007(3) C51 0.128(5) 0.130(5) 0.168(6) -0.034(5) 0.040(5) 0.057(4) C52 0.068(3) 0.049(2) 0.083(3) 0.004(2) 0.009(2) 0.000(2) C53 0.090(4) 0.068(3) 0.070(3) -0.009(2) -0.012(3) 0.008(3) C54 0.083(3) 0.064(3) 0.065(3) -0.020(2) -0.003(2) 0.013(2) C55 0.082(3) 0.039(2) 0.056(2) -0.0033(18) 0.008(2) -0.004(2) C56 0.091(4) 0.067(3) 0.064(3) -0.008(2) 0.004(3) -0.005(3) C57 0.092(4) 0.065(3) 0.068(3) -0.012(2) 0.013(3) 0.002(3) C58 0.078(3) 0.042(2) 0.057(2) -0.0010(18) 0.000(2) -0.003(2) C59 0.105(4) 0.048(2) 0.041(2) -0.0097(18) -0.005(2) -0.001(2) C60 0.101(3) 0.063(3) 0.042(2) -0.004(2) 0.001(2) 0.002(2) C61 0.102(4) 0.067(3) 0.105(4) 0.005(3) 0.008(3) -0.025(3) C62 0.101(5) 0.161(7) 0.199(8) 0.003(6) -0.006(5) -0.019(5) C63 0.080(3) 0.050(2) 0.058(2) -0.0064(19) -0.012(2) 0.001(2) C64 0.114(4) 0.092(4) 0.091(4) -0.021(3) -0.047(3) 0.022(3) C65 0.129(5) 0.077(4) 0.067(3) 0.003(2) -0.018(3) 0.026(3) C66 0.062(3) 0.050(2) 0.059(2) 0.0062(19) 0.0026(19) -0.0021(19) C67 0.071(3) 0.060(3) 0.053(2) 0.003(2) 0.004(2) 0.001(2) C68 0.122(4) 0.075(3) 0.103(4) -0.024(3) 0.001(3) 0.033(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 Cl1 C1 1.753(5) . ? Cl2 C18 1.748(5) . ? Cl3 C35 1.746(5) . ? Cl4 C52 1.734(5) . ? O1 C9 1.177(5) . ? O2 C9 1.301(5) . ? O2 C10 1.497(8) . ? O3 C16 1.192(6) . ? O4 C16 1.328(6) . ? O4 C17 1.453(6) . ? O5 C26 1.181(5) . ? O6 C26 1.313(5) . ? O6 C27 1.439(6) . ? O7 C33 1.189(5) . ? O8 C33 1.339(5) . ? O8 C34 1.452(5) . ? O9 C43 1.177(5) . ? O10 C43 1.309(5) . ? O10 C44 1.513(8) . ? O11 C50 1.175(6) . ? O12 C50 1.349(6) . ? O12 C51 1.463(6) . ? O13 C60 1.198(5) . ? O14 C60 1.301(5) . ? O14 C61 1.436(5) . ? O15 C67 1.183(5) . ? O16 C67 1.341(5) . ? O16 C68 1.452(5) . ? N1 C7 1.454(5) . ? N1 C15 1.457(5) . ? N1 H1 0.8600 . ? N2 C24 1.452(5) . ? N2 C32 1.454(5) . ? N2 H2 0.8600 . ? N3 C49 1.450(5) . ? N3 C41 1.464(5) . ? N3 H3 0.8600 . ? N4 C66 1.458(5) . ? N4 C58 1.466(5) . ? N4 H4 0.8600 . ? C1 C6 1.338(7) . ? C1 C2 1.367(7) . ? C2 C3 1.376(7) . ? C2 H2A 0.9300 . ? C3 C4 1.377(6) . ? C3 H3A 0.9300 . ? C4 C5 1.366(6) . ? C4 C7 1.496(6) . ? C5 C6 1.400(7) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C8 1.554(6) . ? C7 H7 0.9800 . ? C8 C9 1.509(6) . ? C8 C12 1.521(6) . ? C8 H8 0.9800 . ? C10 C11 1.261(10) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 C14 1.493(6) . ? C12 C13 1.497(6) . ? C12 C15 1.538(6) . ? C13 C14 1.495(7) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.500(6) . ? C15 H15 0.9800 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 C19 1.349(7) . ? C18 C23 1.351(6) . ? C19 C20 1.382(7) . ? C19 H19 0.9300 . ? C20 C21 1.370(6) . ? C20 H20 0.9300 . ? C21 C22 1.370(6) . ? C21 C24 1.527(6) . ? C22 C23 1.378(7) . ? C22 H22 0.9300 . ? C23 H23 0.9300 . ? C24 C25 1.557(5) . ? C24 H24 0.9800 . ? C25 C26 1.487(7) . ? C25 C29 1.521(6) . ? C25 H25 0.9800 . ? C27 C28 1.432(9) . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? C29 C30 1.505(6) . ? C29 C31 1.507(7) . ? C29 C32 1.551(6) . ? C30 C31 1.464(8) . ? C30 H30A 0.9700 . ? C30 H30B 0.9700 . ? C31 H31A 0.9700 . ? C31 H31B 0.9700 . ? C32 C33 1.494(6) . ? C32 H32 0.9800 . ? C34 H34A 0.9600 . ? C34 H34B 0.9600 . ? C34 H34C 0.9600 . ? C35 C40 1.355(7) . ? C35 C36 1.365(7) . ? C36 C37 1.385(7) . ? C36 H36 0.9300 . ? C37 C38 1.387(6) . ? C37 H37 0.9300 . ? C38 C39 1.385(6) . ? C38 C41 1.502(6) . ? C39 C40 1.376(6) . ? C39 H39 0.9300 . ? C40 H40 0.9300 . ? C41 C42 1.551(6) . ? C41 H41 0.9800 . ? C42 C43 1.493(6) . ? C42 C46 1.523(6) . ? C42 H42 0.9800 . ? C44 C45 1.258(10) . ? C44 H44A 0.9700 . ? C44 H44B 0.9700 . ? C45 H45A 0.9600 . ? C45 H45B 0.9600 . ? C45 H45C 0.9600 . ? C46 C47 1.495(6) . ? C46 C48 1.496(6) . ? C46 C49 1.557(5) . ? C47 C48 1.498(7) . ? C47 H47A 0.9700 . ? C47 H47B 0.9700 . ? C48 H48A 0.9700 . ? C48 H48B 0.9700 . ? C49 C50 1.509(6) . ? C49 H49 0.9800 . ? C51 H51A 0.9600 . ? C51 H51B 0.9600 . ? C51 H51C 0.9600 . ? C52 C57 1.357(6) . ? C52 C53 1.374(6) . ? C53 C54 1.382(6) . ? C53 H53 0.9300 . ? C54 C55 1.379(5) . ? C54 H54 0.9300 . ? C55 C56 1.383(6) . ? C55 C58 1.501(6) . ? C56 C57 1.387(6) . ? C56 H56 0.9300 . ? C57 H57 0.9300 . ? C58 C59 1.548(5) . ? C58 H58 0.9800 . ? C59 C60 1.483(6) . ? C59 C63 1.532(6) . ? C59 H59 0.9800 . ? C61 C62 1.453(8) . ? C61 H61A 0.9700 . ? C61 H61B 0.9700 . ? C62 H62A 0.9600 . ? C62 H62B 0.9600 . ? C62 H62C 0.9600 . ? C63 C65 1.486(6) . ? C63 C64 1.509(6) . ? C63 C66 1.549(5) . ? C64 C65 1.486(8) . ? C64 H64A 0.9700 . ? C64 H64B 0.9700 . ? C65 H65A 0.9700 . ? C65 H65B 0.9700 . ? C66 C67 1.507(6) . ? C66 H66 0.9800 . ? C68 H68A 0.9600 . ? C68 H68B 0.9600 . ? C68 H68C 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 C9 O2 C10 116.2(4) . . ? C16 O4 C17 116.7(4) . . ? C26 O6 C27 118.2(4) . . ? C33 O8 C34 115.9(4) . . ? C43 O10 C44 116.1(4) . . ? C50 O12 C51 114.4(4) . . ? C60 O14 C61 118.6(4) . . ? C67 O16 C68 115.2(4) . . ? C7 N1 C15 104.2(3) . . ? C7 N1 H1 127.9 . . ? C15 N1 H1 127.9 . . ? C24 N2 C32 107.3(3) . . ? C24 N2 H2 126.3 . . ? C32 N2 H2 126.3 . . ? C49 N3 C41 104.2(3) . . ? C49 N3 H3 127.9 . . ? C41 N3 H3 127.9 . . ? C66 N4 C58 106.9(3) . . ? C66 N4 H4 126.5 . . ? C58 N4 H4 126.5 . . ? C6 C1 C2 122.2(5) . . ? C6 C1 Cl1 118.9(5) . . ? C2 C1 Cl1 118.9(4) . . ? C1 C2 C3 117.6(4) . . ? C1 C2 H2A 121.2 . . ? C3 C2 H2A 121.2 . . ? C2 C3 C4 122.9(4) . . ? C2 C3 H3A 118.6 . . ? C4 C3 H3A 118.6 . . ? C5 C4 C3 117.1(4) . . ? C5 C4 C7 122.4(4) . . ? C3 C4 C7 120.3(4) . . ? C4 C5 C6 121.1(5) . . ? C4 C5 H5 119.4 . . ? C6 C5 H5 119.4 . . ? C1 C6 C5 119.1(5) . . ? C1 C6 H6 120.4 . . ? C5 C6 H6 120.4 . . ? N1 C7 C4 115.3(3) . . ? N1 C7 C8 104.5(3) . . ? C4 C7 C8 117.0(3) . . ? N1 C7 H7 106.4 . . ? C4 C7 H7 106.4 . . ? C8 C7 H7 106.4 . . ? C9 C8 C12 111.5(4) . . ? C9 C8 C7 110.8(4) . . ? C12 C8 C7 101.6(3) . . ? C9 C8 H8 110.9 . . ? C12 C8 H8 110.9 . . ? C7 C8 H8 110.9 . . ? O1 C9 O2 123.1(4) . . ? O1 C9 C8 125.6(4) . . ? O2 C9 C8 111.3(4) . . ? C11 C10 O2 110.9(9) . . ? C11 C10 H10A 109.5 . . ? O2 C10 H10A 109.5 . . ? C11 C10 H10B 109.5 . . ? O2 C10 H10B 109.5 . . ? H10A C10 H10B 108.0 . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C14 C12 C13 60.0(3) . . ? C14 C12 C8 121.6(4) . . ? C13 C12 C8 121.1(4) . . ? C14 C12 C15 122.4(4) . . ? C13 C12 C15 120.6(4) . . ? C8 C12 C15 105.9(3) . . ? C14 C13 C12 59.9(3) . . ? C14 C13 H13A 117.8 . . ? C12 C13 H13A 117.8 . . ? C14 C13 H13B 117.8 . . ? C12 C13 H13B 117.8 . . ? H13A C13 H13B 114.9 . . ? C12 C14 C13 60.1(3) . . ? C12 C14 H14A 117.8 . . ? C13 C14 H14A 117.8 . . ? C12 C14 H14B 117.8 . . ? C13 C14 H14B 117.8 . . ? H14A C14 H14B 114.9 . . ? N1 C15 C16 111.0(4) . . ? N1 C15 C12 106.6(3) . . ? C16 C15 C12 113.8(3) . . ? N1 C15 H15 108.4 . . ? C16 C15 H15 108.4 . . ? C12 C15 H15 108.4 . . ? O3 C16 O4 124.2(5) . . ? O3 C16 C15 125.5(5) . . ? O4 C16 C15 110.3(4) . . ? O4 C17 H17A 109.5 . . ? O4 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? O4 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C19 C18 C23 120.4(5) . . ? C19 C18 Cl2 120.1(4) . . ? C23 C18 Cl2 119.4(4) . . ? C18 C19 C20 120.0(4) . . ? C18 C19 H19 120.0 . . ? C20 C19 H19 120.0 . . ? C21 C20 C19 120.5(4) . . ? C21 C20 H20 119.7 . . ? C19 C20 H20 119.7 . . ? C20 C21 C22 118.3(4) . . ? C20 C21 C24 119.6(4) . . ? C22 C21 C24 122.1(4) . . ? C21 C22 C23 120.8(4) . . ? C21 C22 H22 119.6 . . ? C23 C22 H22 119.6 . . ? C18 C23 C22 119.9(5) . . ? C18 C23 H23 120.0 . . ? C22 C23 H23 120.0 . . ? N2 C24 C21 113.5(3) . . ? N2 C24 C25 105.3(3) . . ? C21 C24 C25 116.2(4) . . ? N2 C24 H24 107.1 . . ? C21 C24 H24 107.1 . . ? C25 C24 H24 107.1 . . ? C26 C25 C29 111.8(4) . . ? C26 C25 C24 116.2(4) . . ? C29 C25 C24 100.8(3) . . ? C26 C25 H25 109.2 . . ? C29 C25 H25 109.2 . . ? C24 C25 H25 109.2 . . ? O5 C26 O6 122.2(5) . . ? O5 C26 C25 124.5(5) . . ? O6 C26 C25 113.3(4) . . ? C28 C27 O6 111.7(6) . . ? C28 C27 H27A 109.3 . . ? O6 C27 H27A 109.3 . . ? C28 C27 H27B 109.3 . . ? O6 C27 H27B 109.3 . . ? H27A C27 H27B 107.9 . . ? C27 C28 H28A 109.5 . . ? C27 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C27 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C30 C29 C31 58.1(3) . . ? C30 C29 C25 122.0(4) . . ? C31 C29 C25 120.3(4) . . ? C30 C29 C32 123.0(4) . . ? C31 C29 C32 120.7(4) . . ? C25 C29 C32 106.5(3) . . ? C31 C30 C29 61.0(3) . . ? C31 C30 H30A 117.7 . . ? C29 C30 H30A 117.7 . . ? C31 C30 H30B 117.7 . . ? C29 C30 H30B 117.7 . . ? H30A C30 H30B 114.8 . . ? C30 C31 C29 60.9(3) . . ? C30 C31 H31A 117.7 . . ? C29 C31 H31A 117.7 . . ? C30 C31 H31B 117.7 . . ? C29 C31 H31B 117.7 . . ? H31A C31 H31B 114.8 . . ? N2 C32 C33 109.9(4) . . ? N2 C32 C29 106.2(3) . . ? C33 C32 C29 112.5(3) . . ? N2 C32 H32 109.4 . . ? C33 C32 H32 109.4 . . ? C29 C32 H32 109.4 . . ? O7 C33 O8 122.4(4) . . ? O7 C33 C32 125.4(5) . . ? O8 C33 C32 112.1(4) . . ? O8 C34 H34A 109.5 . . ? O8 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? O8 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? C40 C35 C36 121.0(5) . . ? C40 C35 Cl3 119.8(4) . . ? C36 C35 Cl3 119.2(4) . . ? C35 C36 C37 119.7(5) . . ? C35 C36 H36 120.2 . . ? C37 C36 H36 120.2 . . ? C36 C37 C38 121.0(5) . . ? C36 C37 H37 119.5 . . ? C38 C37 H37 119.5 . . ? C39 C38 C37 117.0(4) . . ? C39 C38 C41 120.1(4) . . ? C37 C38 C41 122.8(4) . . ? C40 C39 C38 122.2(5) . . ? C40 C39 H39 118.9 . . ? C38 C39 H39 118.9 . . ? C35 C40 C39 119.2(5) . . ? C35 C40 H40 120.4 . . ? C39 C40 H40 120.4 . . ? N3 C41 C38 115.1(3) . . ? N3 C41 C42 104.8(3) . . ? C38 C41 C42 117.2(4) . . ? N3 C41 H41 106.4 . . ? C38 C41 H41 106.4 . . ? C42 C41 H41 106.4 . . ? C43 C42 C46 111.3(4) . . ? C43 C42 C41 110.8(4) . . ? C46 C42 C41 102.0(3) . . ? C43 C42 H42 110.8 . . ? C46 C42 H42 110.8 . . ? C41 C42 H42 110.8 . . ? O9 C43 O10 122.0(4) . . ? O9 C43 C42 127.1(4) . . ? O10 C43 C42 110.9(4) . . ? C45 C44 O10 109.5(9) . . ? C45 C44 H44A 109.8 . . ? O10 C44 H44A 109.8 . . ? C45 C44 H44B 109.8 . . ? O10 C44 H44B 109.8 . . ? H44A C44 H44B 108.2 . . ? C44 C45 H45A 109.5 . . ? C44 C45 H45B 109.5 . . ? H45A C45 H45B 109.5 . . ? C44 C45 H45C 109.5 . . ? H45A C45 H45C 109.5 . . ? H45B C45 H45C 109.5 . . ? C47 C46 C48 60.1(3) . . ? C47 C46 C42 121.8(4) . . ? C48 C46 C42 122.4(4) . . ? C47 C46 C49 120.0(4) . . ? C48 C46 C49 122.2(4) . . ? C42 C46 C49 105.4(3) . . ? C46 C47 C48 60.0(3) . . ? C46 C47 H47A 117.8 . . ? C48 C47 H47A 117.8 . . ? C46 C47 H47B 117.8 . . ? C48 C47 H47B 117.8 . . ? H47A C47 H47B 114.9 . . ? C46 C48 C47 59.9(3) . . ? C46 C48 H48A 117.8 . . ? C47 C48 H48A 117.8 . . ? C46 C48 H48B 117.8 . . ? C47 C48 H48B 117.8 . . ? H48A C48 H48B 114.9 . . ? N3 C49 C50 110.6(4) . . ? N3 C49 C46 106.7(3) . . ? C50 C49 C46 113.2(3) . . ? N3 C49 H49 108.8 . . ? C50 C49 H49 108.8 . . ? C46 C49 H49 108.8 . . ? O11 C50 O12 124.9(5) . . ? O11 C50 C49 126.3(5) . . ? O12 C50 C49 108.8(5) . . ? O12 C51 H51A 109.5 . . ? O12 C51 H51B 109.5 . . ? H51A C51 H51B 109.5 . . ? O12 C51 H51C 109.5 . . ? H51A C51 H51C 109.5 . . ? H51B C51 H51C 109.5 . . ? C57 C52 C53 120.1(4) . . ? C57 C52 Cl4 121.3(4) . . ? C53 C52 Cl4 118.6(4) . . ? C52 C53 C54 119.8(4) . . ? C52 C53 H53 120.1 . . ? C54 C53 H53 120.1 . . ? C55 C54 C53 121.2(4) . . ? C55 C54 H54 119.4 . . ? C53 C54 H54 119.4 . . ? C54 C55 C56 117.9(4) . . ? C54 C55 C58 123.0(4) . . ? C56 C55 C58 119.1(4) . . ? C55 C56 C57 121.0(4) . . ? C55 C56 H56 119.5 . . ? C57 C56 H56 119.5 . . ? C52 C57 C56 120.1(4) . . ? C52 C57 H57 120.0 . . ? C56 C57 H57 120.0 . . ? N4 C58 C55 112.9(3) . . ? N4 C58 C59 105.5(3) . . ? C55 C58 C59 117.3(3) . . ? N4 C58 H58 106.8 . . ? C55 C58 H58 106.8 . . ? C59 C58 H58 106.8 . . ? C60 C59 C63 111.8(3) . . ? C60 C59 C58 115.1(3) . . ? C63 C59 C58 101.2(3) . . ? C60 C59 H59 109.5 . . ? C63 C59 H59 109.5 . . ? C58 C59 H59 109.5 . . ? O13 C60 O14 122.5(4) . . ? O13 C60 C59 122.9(4) . . ? O14 C60 C59 114.5(3) . . ? O14 C61 C62 112.4(5) . . ? O14 C61 H61A 109.1 . . ? C62 C61 H61A 109.1 . . ? O14 C61 H61B 109.1 . . ? C62 C61 H61B 109.1 . . ? H61A C61 H61B 107.9 . . ? C61 C62 H62A 109.5 . . ? C61 C62 H62B 109.5 . . ? H62A C62 H62B 109.5 . . ? C61 C62 H62C 109.5 . . ? H62A C62 H62C 109.5 . . ? H62B C62 H62C 109.5 . . ? C65 C63 C64 59.5(3) . . ? C65 C63 C59 121.8(4) . . ? C64 C63 C59 120.3(4) . . ? C65 C63 C66 123.0(4) . . ? C64 C63 C66 120.0(4) . . ? C59 C63 C66 106.4(3) . . ? C65 C64 C63 59.5(3) . . ? C65 C64 H64A 117.8 . . ? C63 C64 H64A 117.8 . . ? C65 C64 H64B 117.8 . . ? C63 C64 H64B 117.8 . . ? H64A C64 H64B 115.0 . . ? C64 C65 C63 61.0(3) . . ? C64 C65 H65A 117.7 . . ? C63 C65 H65A 117.7 . . ? C64 C65 H65B 117.7 . . ? C63 C65 H65B 117.7 . . ? H65A C65 H65B 114.8 . . ? N4 C66 C67 109.2(3) . . ? N4 C66 C63 106.5(3) . . ? C67 C66 C63 112.4(3) . . ? N4 C66 H66 109.5 . . ? C67 C66 H66 109.5 . . ? C63 C66 H66 109.5 . . ? O15 C67 O16 123.5(4) . . ? O15 C67 C66 125.3(4) . . ? O16 C67 C66 111.3(4) . . ? O16 C68 H68A 109.5 . . ? O16 C68 H68B 109.5 . . ? H68A C68 H68B 109.5 . . ? O16 C68 H68C 109.5 . . ? H68A C68 H68C 109.5 . . ? H68B C68 H68C 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 C6 C1 C2 C3 -1.0(7) . . . . ? Cl1 C1 C2 C3 177.1(4) . . . . ? C1 C2 C3 C4 -0.3(7) . . . . ? C2 C3 C4 C5 1.2(7) . . . . ? C2 C3 C4 C7 -174.0(4) . . . . ? C3 C4 C5 C6 -0.8(7) . . . . ? C7 C4 C5 C6 174.2(4) . . . . ? C2 C1 C6 C5 1.4(7) . . . . ? Cl1 C1 C6 C5 -176.7(4) . . . . ? C4 C5 C6 C1 -0.4(8) . . . . ? C15 N1 C7 C4 172.1(3) . . . . ? C15 N1 C7 C8 42.3(4) . . . . ? C5 C4 C7 N1 -5.3(6) . . . . ? C3 C4 C7 N1 169.6(4) . . . . ? C5 C4 C7 C8 118.2(5) . . . . ? C3 C4 C7 C8 -66.9(5) . . . . ? N1 C7 C8 C9 82.5(4) . . . . ? C4 C7 C8 C9 -46.3(5) . . . . ? N1 C7 C8 C12 -36.1(4) . . . . ? C4 C7 C8 C12 -164.9(3) . . . . ? C10 O2 C9 O1 -6.0(9) . . . . ? C10 O2 C9 C8 172.2(6) . . . . ? C12 C8 C9 O1 61.8(7) . . . . ? C7 C8 C9 O1 -50.7(7) . . . . ? C12 C8 C9 O2 -116.4(4) . . . . ? C7 C8 C9 O2 131.1(4) . . . . ? C9 O2 C10 C11 108.6(10) . . . . ? C9 C8 C12 C14 44.5(5) . . . . ? C7 C8 C12 C14 162.6(4) . . . . ? C9 C8 C12 C13 116.2(4) . . . . ? C7 C8 C12 C13 -125.7(4) . . . . ? C9 C8 C12 C15 -101.6(4) . . . . ? C7 C8 C12 C15 16.5(4) . . . . ? C8 C12 C13 C14 -111.0(5) . . . . ? C15 C12 C13 C14 112.2(5) . . . . ? C8 C12 C14 C13 110.2(5) . . . . ? C15 C12 C14 C13 -109.3(5) . . . . ? C7 N1 C15 C16 -155.7(3) . . . . ? C7 N1 C15 C12 -31.3(4) . . . . ? C14 C12 C15 N1 -137.7(4) . . . . ? C13 C12 C15 N1 150.5(4) . . . . ? C8 C12 C15 N1 8.1(4) . . . . ? C14 C12 C15 C16 -15.0(6) . . . . ? C13 C12 C15 C16 -86.8(5) . . . . ? C8 C12 C15 C16 130.8(4) . . . . ? C17 O4 C16 O3 0.4(7) . . . . ? C17 O4 C16 C15 -178.8(4) . . . . ? N1 C15 C16 O3 32.6(6) . . . . ? C12 C15 C16 O3 -87.6(6) . . . . ? N1 C15 C16 O4 -148.2(4) . . . . ? C12 C15 C16 O4 91.6(4) . . . . ? C23 C18 C19 C20 0.8(7) . . . . ? Cl2 C18 C19 C20 179.2(4) . . . . ? C18 C19 C20 C21 -0.7(7) . . . . ? C19 C20 C21 C22 0.2(7) . . . . ? C19 C20 C21 C24 -177.1(4) . . . . ? C20 C21 C22 C23 0.1(7) . . . . ? C24 C21 C22 C23 177.3(4) . . . . ? C19 C18 C23 C22 -0.5(7) . . . . ? Cl2 C18 C23 C22 -178.9(4) . . . . ? C21 C22 C23 C18 0.0(7) . . . . ? C32 N2 C24 C21 163.6(3) . . . . ? C32 N2 C24 C25 35.4(4) . . . . ? C20 C21 C24 N2 -178.9(4) . . . . ? C22 C21 C24 N2 4.0(5) . . . . ? C20 C21 C24 C25 -56.6(5) . . . . ? C22 C21 C24 C25 126.2(4) . . . . ? N2 C24 C25 C26 84.6(4) . . . . ? C21 C24 C25 C26 -41.9(5) . . . . ? N2 C24 C25 C29 -36.4(4) . . . . ? C21 C24 C25 C29 -162.9(3) . . . . ? C27 O6 C26 O5 2.5(8) . . . . ? C27 O6 C26 C25 -175.3(4) . . . . ? C29 C25 C26 O5 -99.8(6) . . . . ? C24 C25 C26 O5 145.2(6) . . . . ? C29 C25 C26 O6 78.0(5) . . . . ? C24 C25 C26 O6 -37.0(6) . . . . ? C26 O6 C27 C28 -83.0(7) . . . . ? C26 C25 C29 C30 48.8(5) . . . . ? C24 C25 C29 C30 172.9(4) . . . . ? C26 C25 C29 C31 118.0(4) . . . . ? C24 C25 C29 C31 -118.0(4) . . . . ? C26 C25 C29 C32 -99.9(4) . . . . ? C24 C25 C29 C32 24.2(4) . . . . ? C25 C29 C30 C31 108.2(5) . . . . ? C32 C29 C30 C31 -108.2(5) . . . . ? C25 C29 C31 C30 -111.0(5) . . . . ? C32 C29 C31 C30 112.1(5) . . . . ? C24 N2 C32 C33 -141.3(3) . . . . ? C24 N2 C32 C29 -19.3(4) . . . . ? C30 C29 C32 N2 -152.8(4) . . . . ? C31 C29 C32 N2 137.5(4) . . . . ? C25 C29 C32 N2 -4.5(4) . . . . ? C30 C29 C32 C33 -32.5(6) . . . . ? C31 C29 C32 C33 -102.2(5) . . . . ? C25 C29 C32 C33 115.8(4) . . . . ? C34 O8 C33 O7 1.7(6) . . . . ? C34 O8 C33 C32 -179.0(4) . . . . ? N2 C32 C33 O7 22.3(6) . . . . ? C29 C32 C33 O7 -95.9(5) . . . . ? N2 C32 C33 O8 -157.0(3) . . . . ? C29 C32 C33 O8 84.9(5) . . . . ? C40 C35 C36 C37 0.1(8) . . . . ? Cl3 C35 C36 C37 -177.2(4) . . . . ? C35 C36 C37 C38 0.4(8) . . . . ? C36 C37 C38 C39 -1.3(7) . . . . ? C36 C37 C38 C41 175.1(4) . . . . ? C37 C38 C39 C40 1.6(7) . . . . ? C41 C38 C39 C40 -174.9(4) . . . . ? C36 C35 C40 C39 0.2(7) . . . . ? Cl3 C35 C40 C39 177.5(4) . . . . ? C38 C39 C40 C35 -1.1(7) . . . . ? C49 N3 C41 C38 172.4(3) . . . . ? C49 N3 C41 C42 42.2(4) . . . . ? C39 C38 C41 N3 171.3(4) . . . . ? C37 C38 C41 N3 -5.0(6) . . . . ? C39 C38 C41 C42 -64.9(5) . . . . ? C37 C38 C41 C42 118.8(5) . . . . ? N3 C41 C42 C43 82.7(4) . . . . ? C38 C41 C42 C43 -46.2(5) . . . . ? N3 C41 C42 C46 -35.8(4) . . . . ? C38 C41 C42 C46 -164.7(3) . . . . ? C44 O10 C43 O9 -5.7(9) . . . . ? C44 O10 C43 C42 172.7(6) . . . . ? C46 C42 C43 O9 64.8(7) . . . . ? C41 C42 C43 O9 -47.9(7) . . . . ? C46 C42 C43 O10 -113.5(4) . . . . ? C41 C42 C43 O10 133.8(4) . . . . ? C43 O10 C44 C45 105.8(10) . . . . ? C43 C42 C46 C47 116.7(4) . . . . ? C41 C42 C46 C47 -125.1(4) . . . . ? C43 C42 C46 C48 44.2(5) . . . . ? C41 C42 C46 C48 162.4(4) . . . . ? C43 C42 C46 C49 -102.0(4) . . . . ? C41 C42 C46 C49 16.2(4) . . . . ? C42 C46 C47 C48 -111.8(5) . . . . ? C49 C46 C47 C48 112.3(5) . . . . ? C42 C46 C48 C47 110.7(5) . . . . ? C49 C46 C48 C47 -108.6(5) . . . . ? C41 N3 C49 C50 -154.8(3) . . . . ? C41 N3 C49 C46 -31.3(4) . . . . ? C47 C46 C49 N3 150.6(4) . . . . ? C48 C46 C49 N3 -137.8(4) . . . . ? C42 C46 C49 N3 8.5(4) . . . . ? C47 C46 C49 C50 -87.5(5) . . . . ? C48 C46 C49 C50 -15.9(6) . . . . ? C42 C46 C49 C50 130.3(4) . . . . ? C51 O12 C50 O11 -1.1(7) . . . . ? C51 O12 C50 C49 -179.5(4) . . . . ? N3 C49 C50 O11 34.2(6) . . . . ? C46 C49 C50 O11 -85.5(6) . . . . ? N3 C49 C50 O12 -147.4(4) . . . . ? C46 C49 C50 O12 93.0(4) . . . . ? C57 C52 C53 C54 -0.4(7) . . . . ? Cl4 C52 C53 C54 -178.4(4) . . . . ? C52 C53 C54 C55 0.1(7) . . . . ? C53 C54 C55 C56 0.3(7) . . . . ? C53 C54 C55 C58 177.3(4) . . . . ? C54 C55 C56 C57 -0.4(6) . . . . ? C58 C55 C56 C57 -177.6(4) . . . . ? C53 C52 C57 C56 0.2(7) . . . . ? Cl4 C52 C57 C56 178.2(3) . . . . ? C55 C56 C57 C52 0.2(7) . . . . ? C66 N4 C58 C55 164.8(3) . . . . ? C66 N4 C58 C59 35.4(4) . . . . ? C54 C55 C58 N4 2.4(5) . . . . ? C56 C55 C58 N4 179.4(3) . . . . ? C54 C55 C58 C59 125.4(4) . . . . ? C56 C55 C58 C59 -57.5(5) . . . . ? N4 C58 C59 C60 84.9(4) . . . . ? C55 C58 C59 C60 -41.9(5) . . . . ? N4 C58 C59 C63 -35.9(4) . . . . ? C55 C58 C59 C63 -162.6(3) . . . . ? C61 O14 C60 O13 -1.2(7) . . . . ? C61 O14 C60 C59 -177.4(4) . . . . ? C63 C59 C60 O13 -99.7(5) . . . . ? C58 C59 C60 O13 145.6(5) . . . . ? C63 C59 C60 O14 76.4(4) . . . . ? C58 C59 C60 O14 -38.3(5) . . . . ? C60 O14 C61 C62 -81.0(6) . . . . ? C60 C59 C63 C65 48.6(5) . . . . ? C58 C59 C63 C65 171.7(4) . . . . ? C60 C59 C63 C64 119.4(4) . . . . ? C58 C59 C63 C64 -117.6(4) . . . . ? C60 C59 C63 C66 -99.6(4) . . . . ? C58 C59 C63 C66 23.4(4) . . . . ? C59 C63 C64 C65 -111.3(5) . . . . ? C66 C63 C64 C65 112.9(5) . . . . ? C59 C63 C65 C64 108.9(5) . . . . ? C66 C63 C65 C64 -108.1(5) . . . . ? C58 N4 C66 C67 -141.3(3) . . . . ? C58 N4 C66 C63 -19.7(4) . . . . ? C65 C63 C66 N4 -151.2(4) . . . . ? C64 C63 C66 N4 137.7(4) . . . . ? C59 C63 C66 N4 -3.5(4) . . . . ? C65 C63 C66 C67 -31.7(6) . . . . ? C64 C63 C66 C67 -102.8(5) . . . . ? C59 C63 C66 C67 116.1(4) . . . . ? C68 O16 C67 O15 3.0(6) . . . . ? C68 O16 C67 C66 -177.9(4) . . . . ? N4 C66 C67 O15 22.6(5) . . . . ? C63 C66 C67 O15 -95.4(5) . . . . ? N4 C66 C67 O16 -156.5(3) . . . . ? C63 C66 C67 O16 85.6(4) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.25 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.278 _refine_diff_density_min -0.225 _refine_diff_density_rms 0.033