# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email LIsaacs@umd.edu _publ_contact_author_name 'Lyle Isaacs' loop_ _publ_author_name 'Liping Cao' 'Jun-Gang Wang' 'Jiao-Yang Ding' 'Anxin Wu' 'Lyle Isaacs' # end Validation Reply Form #===END data_100401dm _database_code_depnum_ccdc_archive 'CCDC 782746' #TrackingRef '- CIFs Combined CC.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C54 H54 Cl2 N12 O16, 2(C H2 Cl2), C H4 O ' _chemical_formula_sum 'C57 H62 Cl6 N12 O17' _chemical_formula_weight 1399.89 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 14.4991(10) _cell_length_b 15.5113(11) _cell_length_c 16.0201(11) _cell_angle_alpha 83.9240(10) _cell_angle_beta 67.4170(10) _cell_angle_gamma 71.8860(10) _cell_volume 3161.4(4) _cell_formula_units_Z 2 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 5352 _cell_measurement_theta_min 2.62 _cell_measurement_theta_max 28.23 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.471 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1452 _exptl_absorpt_coefficient_mu 0.351 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9460 _exptl_absorpt_correction_T_max 0.9657 _exptl_absorpt_process_details 'SADABS, (Sheldrick,1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20709 _diffrn_reflns_av_R_equivalents 0.1005 _diffrn_reflns_av_sigmaI/netI 0.0849 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 25.50 _reflns_number_total 11641 _reflns_number_gt 9731 _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 '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^)+(0.1070P)^2^+4.4211P] 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 11641 _refine_ls_number_parameters 878 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.0843 _refine_ls_R_factor_gt 0.0746 _refine_ls_wR_factor_ref 0.2108 _refine_ls_wR_factor_gt 0.2021 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.078 _refine_ls_shift/su_max 0.004 _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 0.6386(3) 0.2661(2) 1.0318(2) 0.0261(7) Uani 1 1 d . . . C2 C 0.5838(3) 0.3504(3) 1.0148(2) 0.0339(8) Uani 1 1 d . . . H2 H 0.5122 0.3756 1.0513 0.041 Uiso 1 1 calc R . . C3 C 0.6344(3) 0.3988(2) 0.9431(2) 0.0322(8) Uani 1 1 d . . . H3 H 0.5972 0.4577 0.9307 0.039 Uiso 1 1 calc R . . C4 C 0.7395(3) 0.3613(2) 0.8892(2) 0.0231(7) Uani 1 1 d . . . C5 C 0.7924(3) 0.2761(3) 0.9087(2) 0.0339(8) Uani 1 1 d . . . H5 H 0.8642 0.2504 0.8730 0.041 Uiso 1 1 calc R . . C6 C 0.7421(3) 0.2274(3) 0.9799(2) 0.0351(8) Uani 1 1 d . . . H6 H 0.7786 0.1683 0.9926 0.042 Uiso 1 1 calc R . . C7 C 0.8542(2) 0.3739(2) 0.73474(19) 0.0191(6) Uani 1 1 d . . . C8 C 0.9788(2) 0.39898(19) 0.58812(19) 0.0181(6) Uani 1 1 d . . . C9 C 0.9634(2) 0.35870(19) 0.52219(19) 0.0179(6) Uani 1 1 d . . . C10 C 1.0472(2) 0.32946(19) 0.43980(19) 0.0179(6) Uani 1 1 d . . . C11 C 1.1435(2) 0.34295(19) 0.42390(19) 0.0186(6) Uani 1 1 d . . . C12 C 1.1582(2) 0.3829(2) 0.4898(2) 0.0210(6) Uani 1 1 d . . . H12 H 1.2239 0.3915 0.4791 0.025 Uiso 1 1 calc R . . C13 C 1.0757(2) 0.4100(2) 0.5710(2) 0.0204(6) Uani 1 1 d . . . H13 H 1.0856 0.4369 0.6163 0.024 Uiso 1 1 calc R . . C14 C 1.3208(3) 0.3259(3) 0.3248(2) 0.0289(7) Uani 1 1 d . . . H14A H 1.3125 0.3900 0.3326 0.043 Uiso 1 1 calc R . . H14B H 1.3683 0.3059 0.2630 0.043 Uiso 1 1 calc R . . H14C H 1.3499 0.2896 0.3678 0.043 Uiso 1 1 calc R . . C15 C 0.8573(2) 0.3461(2) 0.5405(2) 0.0197(6) Uani 1 1 d . . . H15A H 0.8644 0.2804 0.5437 0.024 Uiso 1 1 calc R . . H15B H 0.8079 0.3737 0.6002 0.024 Uiso 1 1 calc R . . C16 C 1.0362(2) 0.2829(2) 0.3677(2) 0.0208(6) Uani 1 1 d . . . H16A H 1.1048 0.2650 0.3170 0.025 Uiso 1 1 calc R . . H16B H 1.0181 0.2266 0.3930 0.025 Uiso 1 1 calc R . . C17 C 0.7265(2) 0.4592(2) 0.48946(19) 0.0177(6) Uani 1 1 d . . . C18 C 0.9713(2) 0.4111(2) 0.27848(19) 0.0198(6) Uani 1 1 d . . . C19 C 0.8492(2) 0.3474(2) 0.38355(19) 0.0185(6) Uani 1 1 d . . . C20 C 0.8254(2) 0.2571(2) 0.3829(2) 0.0228(6) Uani 1 1 d . . . C21 C 0.7240(3) 0.1607(2) 0.4647(3) 0.0316(8) Uani 1 1 d . . . H21A H 0.7850 0.1066 0.4409 0.038 Uiso 1 1 calc R . . H21B H 0.6807 0.1702 0.4276 0.038 Uiso 1 1 calc R . . C22 C 0.6612(3) 0.1480(2) 0.5618(3) 0.0364(8) Uani 1 1 d . . . H22A H 0.7061 0.1350 0.5971 0.055 Uiso 1 1 calc R . . H22B H 0.6330 0.0971 0.5663 0.055 Uiso 1 1 calc R . . H22C H 0.6035 0.2034 0.5854 0.055 Uiso 1 1 calc R . . C23 C 0.7913(2) 0.4255(2) 0.33410(19) 0.0192(6) Uani 1 1 d . . . C24 C 0.7455(2) 0.3911(2) 0.2758(2) 0.0222(6) Uani 1 1 d . . . C25 C 0.6109(3) 0.3323(2) 0.2812(2) 0.0265(7) Uani 1 1 d . . . H25A H 0.5681 0.2956 0.3233 0.032 Uiso 1 1 calc R . . H25B H 0.6648 0.2927 0.2299 0.032 Uiso 1 1 calc R . . C26 C 0.5430(3) 0.4094(3) 0.2472(3) 0.0351(8) Uani 1 1 d . . . H26A H 0.4920 0.4502 0.2978 0.053 Uiso 1 1 calc R . . H26B H 0.5061 0.3857 0.2194 0.053 Uiso 1 1 calc R . . H26C H 0.5863 0.4429 0.2022 0.053 Uiso 1 1 calc R . . C27 C 0.8673(2) 0.5346(2) 0.21081(19) 0.0213(6) Uani 1 1 d . . . H27A H 0.9388 0.5325 0.1683 0.026 Uiso 1 1 calc R . . H27B H 0.8303 0.5208 0.1757 0.026 Uiso 1 1 calc R . . C28 C 0.6243(2) 0.5567(2) 0.4043(2) 0.0204(6) Uani 1 1 d . . . H28A H 0.5665 0.5655 0.4642 0.024 Uiso 1 1 calc R . . H28B H 0.5989 0.5409 0.3604 0.024 Uiso 1 1 calc R . . C29 C 0.5974(2) 0.7168(2) 0.4355(2) 0.0214(6) Uani 1 1 d . . . C30 C 0.8678(2) 0.6852(2) 0.24924(19) 0.0206(6) Uani 1 1 d . . . C31 C 0.7017(2) 0.6654(2) 0.2852(2) 0.0219(6) Uani 1 1 d . . . C32 C 0.6505(3) 0.6545(2) 0.2195(2) 0.0256(7) Uani 1 1 d . . . C33 C 0.4903(3) 0.6652(3) 0.2072(2) 0.0317(8) Uani 1 1 d . . . H33A H 0.5229 0.6124 0.1651 0.038 Uiso 1 1 calc R . . H33B H 0.4869 0.7214 0.1714 0.038 Uiso 1 1 calc R . . C34 C 0.3832(3) 0.6646(3) 0.2706(3) 0.0340(8) Uani 1 1 d . . . H34A H 0.3879 0.6089 0.3059 0.051 Uiso 1 1 calc R . . H34B H 0.3396 0.6673 0.2359 0.051 Uiso 1 1 calc R . . H34C H 0.3519 0.7173 0.3116 0.051 Uiso 1 1 calc R . . C35 C 0.6913(2) 0.7678(2) 0.2963(2) 0.0232(7) Uani 1 1 d . . . C36 C 0.6528(3) 0.8287(2) 0.2248(2) 0.0300(8) Uani 1 1 d D . . C37 C 0.6961(9) 0.9098(9) 0.0875(7) 0.046(2) Uani 0.52 1 d PD A 1 H37A H 0.6697 0.8752 0.0579 0.055 Uiso 0.52 1 calc PR A 1 H37B H 0.6411 0.9673 0.1123 0.055 Uiso 0.52 1 calc PR A 1 C38 C 0.7916(10) 0.9278(9) 0.0229(7) 0.054(2) Uani 0.52 1 d PD A 1 H38A H 0.8162 0.9626 0.0531 0.081 Uiso 0.52 1 calc PR A 1 H38B H 0.7768 0.9627 -0.0276 0.081 Uiso 0.52 1 calc PR A 1 H38C H 0.8456 0.8702 -0.0001 0.081 Uiso 0.52 1 calc PR A 1 O14 O 0.7257(6) 0.8562(5) 0.1600(4) 0.034(2) Uani 0.52 1 d PD A 1 C39 C 0.5983(3) 0.8768(2) 0.4293(2) 0.0274(7) Uani 1 1 d . A . H39A H 0.5318 0.8885 0.4824 0.033 Uiso 1 1 calc R . . H39B H 0.5900 0.9268 0.3865 0.033 Uiso 1 1 calc R . . C40 C 0.8191(3) 0.8449(2) 0.3005(2) 0.0266(7) Uani 1 1 d . A . H40A H 0.7821 0.8980 0.2737 0.032 Uiso 1 1 calc R . . H40B H 0.8951 0.8362 0.2692 0.032 Uiso 1 1 calc R . . C41 C 0.6838(3) 0.8794(2) 0.4604(2) 0.0260(7) Uani 1 1 d . . . C42 C 0.7883(3) 0.8650(2) 0.4004(2) 0.0249(7) Uani 1 1 d . . . C43 C 0.8622(3) 0.8733(2) 0.4321(2) 0.0274(7) Uani 1 1 d . . . C44 C 0.8338(3) 0.8959(2) 0.5220(2) 0.0313(8) Uani 1 1 d . . . H44 H 0.8846 0.9026 0.5425 0.038 Uiso 1 1 calc R . . C45 C 0.7317(3) 0.9085(2) 0.5819(2) 0.0313(8) Uani 1 1 d . . . H45 H 0.7126 0.9231 0.6436 0.038 Uiso 1 1 calc R . . C46 C 0.6577(3) 0.8999(2) 0.5517(2) 0.0279(7) Uani 1 1 d . . . C47 C 1.0147(3) 0.9255(2) 0.3485(2) 0.0319(8) Uani 1 1 d . . . C48 C 1.1843(3) 0.9486(3) 0.2452(2) 0.0341(8) Uani 1 1 d . . . C49 C 1.1524(4) 1.0426(3) 0.2454(3) 0.0529(12) Uani 1 1 d . . . H49 H 1.0819 1.0753 0.2786 0.063 Uiso 1 1 calc R . . C50 C 1.2250(5) 1.0886(4) 0.1964(3) 0.0653(16) Uani 1 1 d . . . H50 H 1.2034 1.1530 0.1949 0.078 Uiso 1 1 calc R . . C51 C 1.3262(4) 1.0417(4) 0.1508(3) 0.0591(15) Uani 1 1 d . . . C52 C 1.3587(4) 0.9495(4) 0.1485(4) 0.0736(19) Uani 1 1 d . . . H52 H 1.4293 0.9174 0.1147 0.088 Uiso 1 1 calc R . . C53 C 1.2872(3) 0.9033(4) 0.1963(4) 0.0651(16) Uani 1 1 d . . . H53 H 1.3095 0.8389 0.1953 0.078 Uiso 1 1 calc R . . C54 C 0.5281(3) 0.9247(3) 0.7010(2) 0.0416(9) Uani 1 1 d . . . H54A H 0.5717 0.8733 0.7232 0.062 Uiso 1 1 calc R . . H54B H 0.4543 0.9283 0.7335 0.062 Uiso 1 1 calc R . . H54C H 0.5398 0.9810 0.7111 0.062 Uiso 1 1 calc R . . C55 C 0.9180(5) 0.0632(3) 0.1878(4) 0.0658(15) Uani 1 1 d . . . H55A H 0.9173 0.0543 0.2501 0.079 Uiso 1 1 calc R . . H55B H 0.9482 0.1135 0.1610 0.079 Uiso 1 1 calc R . . C56 C 0.9497(4) 0.3295(3) -0.0007(3) 0.0672(15) Uani 1 1 d D . . H56A H 0.9494 0.3506 -0.0611 0.081 Uiso 0.62 1 calc PR B 1 H56B H 0.8786 0.3539 0.0451 0.081 Uiso 0.62 1 calc PR B 1 H56C H 0.9099 0.2956 0.0484 0.081 Uiso 0.38 1 d PR B 2 H56D H 0.9802 0.2954 -0.0587 0.081 Uiso 0.38 1 d PR B 2 C57 C 0.2785(5) 0.3800(5) 0.0594(3) 0.0698(17) Uani 1 1 d . . . H57A H 0.2075 0.4016 0.0589 0.105 Uiso 1 1 calc R . . H57B H 0.3072 0.3148 0.0455 0.105 Uiso 1 1 calc R . . H57C H 0.3227 0.4123 0.0138 0.105 Uiso 1 1 calc R . . Cl1 Cl 0.57496(7) 0.20441(6) 1.12083(6) 0.0360(2) Uani 1 1 d . . . Cl2 Cl 1.41633(15) 1.10121(14) 0.09151(10) 0.0929(6) Uani 1 1 d . . . Cl3 Cl 0.78921(14) 0.09229(11) 0.19120(14) 0.0915(6) Uani 1 1 d . . . Cl4 Cl 0.99638(10) -0.03682(8) 0.12344(7) 0.0536(3) Uani 1 1 d . . . Cl5 Cl 1.04046(16) 0.36211(18) 0.02370(17) 0.1171(8) Uani 1 1 d D C . Cl6 Cl 0.9945(2) 0.20451(15) 0.0022(2) 0.0749(7) Uani 0.62 1 d PD C 1 Cl6' Cl 0.8695(4) 0.4517(3) -0.0099(3) 0.0953(14) Uani 0.38 1 d PD C 2 N1 N 0.7879(2) 0.41209(19) 0.81721(17) 0.0237(6) Uani 1 1 d . . . H1 H 0.7750 0.4705 0.8256 0.028 Uiso 1 1 calc R . . N2 N 0.8966(2) 0.43243(17) 0.67297(16) 0.0191(5) Uani 1 1 d . . . H2A H 0.8734 0.4910 0.6854 0.023 Uiso 1 1 calc R . . N3 N 0.8135(2) 0.38623(17) 0.47217(16) 0.0182(5) Uani 1 1 d . . . N4 N 0.9576(2) 0.33731(17) 0.33169(16) 0.0193(5) Uani 1 1 d . . . N5 N 0.7104(2) 0.48182(17) 0.40911(16) 0.0193(5) Uani 1 1 d . . . N6 N 0.8750(2) 0.46368(17) 0.27842(16) 0.0197(5) Uani 1 1 d . . . N7 N 0.6491(2) 0.64173(18) 0.37775(16) 0.0202(5) Uani 1 1 d . . . N8 N 0.8140(2) 0.62506(18) 0.24794(17) 0.0214(5) Uani 1 1 d . . . N9 N 0.6158(2) 0.79208(18) 0.38580(18) 0.0244(6) Uani 1 1 d . . . N10 N 0.7954(2) 0.76539(18) 0.28491(17) 0.0224(6) Uani 1 1 d . . . N11 N 0.9689(2) 0.8574(2) 0.3732(2) 0.0297(6) Uani 1 1 d . . . H11 H 1.0063 0.8021 0.3522 0.036 Uiso 1 1 calc R . . N12 N 1.1184(2) 0.8950(2) 0.2915(2) 0.0349(7) Uani 1 1 d . . . H12A H 1.1459 0.8359 0.2833 0.042 Uiso 1 1 calc R . . O1 O 0.86952(17) 0.29460(14) 0.71571(14) 0.0213(5) Uani 1 1 d . . . O2 O 1.22090(17) 0.31436(15) 0.34115(14) 0.0238(5) Uani 1 1 d . . . O3 O 0.67181(17) 0.49841(14) 0.56150(13) 0.0212(5) Uani 1 1 d . . . O4 O 1.05435(16) 0.42738(15) 0.23876(14) 0.0228(5) Uani 1 1 d . . . O5 O 0.8636(2) 0.21127(16) 0.31524(16) 0.0325(6) Uani 1 1 d . . . O6 O 0.75866(18) 0.24091(15) 0.46155(15) 0.0260(5) Uani 1 1 d . . . O7 O 0.7839(2) 0.38590(19) 0.19499(15) 0.0334(6) Uani 1 1 d . . . O8 O 0.66176(18) 0.36745(16) 0.32825(14) 0.0244(5) Uani 1 1 d . . . O9 O 0.54453(18) 0.71652(15) 0.51502(15) 0.0266(5) Uani 1 1 d . . . O10 O 0.96167(17) 0.66759(16) 0.22280(14) 0.0239(5) Uani 1 1 d . . . O11 O 0.6962(2) 0.6468(2) 0.13964(17) 0.0460(8) Uani 1 1 d . . . O12 O 0.55067(17) 0.66062(17) 0.26365(15) 0.0269(5) Uani 1 1 d . . . O13 O 0.5633(2) 0.85740(18) 0.23512(18) 0.0380(6) Uani 1 1 d . A . O15 O 0.5553(2) 0.91229(17) 0.60612(16) 0.0347(6) Uani 1 1 d . . . O16 O 0.9695(2) 1.00432(18) 0.3733(2) 0.0446(7) Uani 1 1 d . . . O17 O 0.2754(2) 0.39614(18) 0.14558(17) 0.0357(6) Uani 1 1 d . . . H17 H 0.218(4) 0.380(3) 0.179(3) 0.054 Uiso 1 1 d . . . C38' C 0.7275(11) 0.9595(6) 0.0564(7) 0.042(2) Uani 0.48 1 d PD A 2 H38D H 0.6708 0.9973 0.1068 0.063 Uiso 0.48 1 calc PR A 2 H38E H 0.7215 0.9840 -0.0008 0.063 Uiso 0.48 1 calc PR A 2 H38F H 0.7949 0.9595 0.0568 0.063 Uiso 0.48 1 calc PR A 2 C37' C 0.7202(7) 0.8628(7) 0.0665(5) 0.0292(19) Uani 0.48 1 d PD A 2 H37C H 0.6499 0.8636 0.0711 0.035 Uiso 0.48 1 calc PR A 2 H37D H 0.7722 0.8267 0.0120 0.035 Uiso 0.48 1 calc PR A 2 O14' O 0.7393(7) 0.8189(5) 0.1477(5) 0.032(2) Uani 0.48 1 d PD A 2 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 0.0314(17) 0.0280(17) 0.0189(15) 0.0053(13) -0.0049(13) -0.0160(14) C2 0.0271(18) 0.0335(19) 0.0262(17) 0.0024(14) 0.0036(14) -0.0066(15) C3 0.0306(18) 0.0231(17) 0.0262(17) 0.0017(13) -0.0002(14) 0.0009(14) C4 0.0271(16) 0.0257(17) 0.0155(14) 0.0040(12) -0.0053(13) -0.0110(13) C5 0.0224(17) 0.042(2) 0.0257(17) 0.0123(15) -0.0039(14) -0.0039(15) C6 0.0347(19) 0.0324(19) 0.0242(17) 0.0121(14) -0.0039(15) -0.0038(15) C7 0.0183(14) 0.0228(16) 0.0158(14) 0.0054(11) -0.0066(12) -0.0068(12) C8 0.0224(15) 0.0145(14) 0.0147(13) 0.0060(11) -0.0052(12) -0.0057(11) C9 0.0213(15) 0.0143(14) 0.0171(14) 0.0059(11) -0.0066(12) -0.0061(11) C10 0.0217(15) 0.0128(13) 0.0168(14) 0.0030(11) -0.0069(12) -0.0029(11) C11 0.0195(15) 0.0137(14) 0.0167(14) 0.0035(11) -0.0032(12) -0.0027(11) C12 0.0221(15) 0.0197(15) 0.0216(15) 0.0058(12) -0.0069(12) -0.0098(12) C13 0.0259(16) 0.0203(15) 0.0166(14) 0.0056(11) -0.0090(12) -0.0095(13) C14 0.0206(16) 0.0352(19) 0.0253(16) 0.0003(14) -0.0017(13) -0.0092(14) C15 0.0212(15) 0.0219(15) 0.0161(14) 0.0048(11) -0.0067(12) -0.0083(12) C16 0.0231(15) 0.0165(15) 0.0200(14) 0.0029(11) -0.0065(12) -0.0046(12) C17 0.0186(14) 0.0200(15) 0.0158(14) 0.0040(11) -0.0043(12) -0.0113(12) C18 0.0240(16) 0.0206(15) 0.0152(14) -0.0003(11) -0.0066(12) -0.0077(12) C19 0.0202(15) 0.0212(15) 0.0141(13) 0.0015(11) -0.0051(12) -0.0078(12) C20 0.0235(16) 0.0215(16) 0.0241(16) 0.0011(13) -0.0093(13) -0.0073(13) C21 0.0367(19) 0.0215(17) 0.041(2) 0.0032(14) -0.0125(16) -0.0171(15) C22 0.037(2) 0.0239(18) 0.046(2) 0.0088(15) -0.0103(17) -0.0161(16) C23 0.0195(14) 0.0224(15) 0.0146(14) 0.0029(11) -0.0040(12) -0.0085(12) C24 0.0218(15) 0.0265(17) 0.0180(15) 0.0017(12) -0.0059(12) -0.0090(13) C25 0.0287(17) 0.0311(18) 0.0241(16) -0.0009(13) -0.0077(13) -0.0170(14) C26 0.0268(18) 0.040(2) 0.039(2) -0.0075(16) -0.0122(16) -0.0084(16) C27 0.0213(15) 0.0274(17) 0.0122(13) 0.0073(12) -0.0043(12) -0.0078(13) C28 0.0196(15) 0.0227(16) 0.0180(14) 0.0046(12) -0.0058(12) -0.0080(12) C29 0.0181(14) 0.0219(16) 0.0221(16) 0.0066(12) -0.0070(12) -0.0056(12) C30 0.0205(16) 0.0272(16) 0.0133(13) 0.0087(12) -0.0068(12) -0.0080(13) C31 0.0188(15) 0.0258(16) 0.0169(14) 0.0075(12) -0.0046(12) -0.0059(12) C32 0.0225(16) 0.0305(18) 0.0222(16) 0.0067(13) -0.0088(13) -0.0069(13) C33 0.0291(18) 0.044(2) 0.0294(17) 0.0119(15) -0.0179(15) -0.0151(16) C34 0.0262(18) 0.041(2) 0.040(2) 0.0101(16) -0.0164(16) -0.0145(16) C35 0.0183(15) 0.0274(17) 0.0199(15) 0.0102(13) -0.0052(12) -0.0068(13) C36 0.0310(19) 0.0293(18) 0.0319(18) 0.0162(14) -0.0155(15) -0.0121(15) C37 0.058(6) 0.044(6) 0.041(5) 0.019(6) -0.033(5) -0.011(6) C38 0.074(7) 0.065(7) 0.034(5) 0.023(5) -0.026(5) -0.034(6) O14 0.036(4) 0.035(5) 0.035(4) 0.029(3) -0.019(3) -0.019(4) C39 0.0236(16) 0.0189(16) 0.0302(17) 0.0060(13) -0.0043(14) -0.0028(13) C40 0.0255(16) 0.0229(16) 0.0265(16) 0.0092(13) -0.0040(13) -0.0105(13) C41 0.0263(16) 0.0159(15) 0.0280(17) 0.0088(12) -0.0047(14) -0.0050(13) C42 0.0261(16) 0.0152(15) 0.0261(16) 0.0092(12) -0.0045(13) -0.0057(12) C43 0.0263(17) 0.0168(15) 0.0314(17) 0.0073(13) -0.0078(14) -0.0021(13) C44 0.0347(19) 0.0231(17) 0.0323(18) 0.0073(14) -0.0148(15) -0.0027(14) C45 0.038(2) 0.0195(16) 0.0270(17) 0.0052(13) -0.0104(15) 0.0000(14) C46 0.0285(17) 0.0153(15) 0.0260(16) 0.0069(12) -0.0011(14) -0.0015(13) C47 0.0317(18) 0.0265(19) 0.0340(18) 0.0096(14) -0.0118(15) -0.0074(15) C48 0.037(2) 0.041(2) 0.0309(18) 0.0109(15) -0.0148(16) -0.0203(17) C49 0.071(3) 0.046(3) 0.036(2) -0.0088(18) 0.003(2) -0.036(2) C50 0.108(5) 0.059(3) 0.036(2) -0.008(2) -0.002(3) -0.062(3) C51 0.075(3) 0.106(4) 0.035(2) 0.027(2) -0.030(2) -0.074(3) C52 0.035(2) 0.096(4) 0.090(4) 0.062(3) -0.030(3) -0.031(3) C53 0.028(2) 0.071(3) 0.083(4) 0.047(3) -0.018(2) -0.015(2) C54 0.046(2) 0.034(2) 0.0238(18) 0.0061(15) 0.0023(16) -0.0041(17) C55 0.096(4) 0.040(3) 0.069(3) -0.012(2) -0.051(3) -0.001(3) C56 0.082(4) 0.075(4) 0.040(3) -0.013(2) 0.001(2) -0.043(3) C57 0.072(4) 0.100(5) 0.043(3) -0.019(3) -0.002(2) -0.050(3) Cl1 0.0421(5) 0.0352(5) 0.0285(4) 0.0101(3) -0.0034(4) -0.0242(4) Cl2 0.1139(13) 0.1581(17) 0.0642(8) 0.0475(9) -0.0450(9) -0.1174(14) Cl3 0.0975(12) 0.0589(9) 0.1297(15) -0.0286(9) -0.0768(12) 0.0152(8) Cl4 0.0657(7) 0.0454(6) 0.0425(6) -0.0049(5) -0.0104(5) -0.0173(5) Cl5 0.0771(11) 0.148(2) 0.1266(17) -0.0424(15) -0.0176(12) -0.0454(13) Cl6 0.0735(14) 0.0540(12) 0.113(2) 0.0026(12) -0.0481(14) -0.0234(11) Cl6' 0.136(4) 0.103(3) 0.055(2) 0.008(2) -0.039(3) -0.044(3) N1 0.0287(14) 0.0218(14) 0.0165(12) 0.0023(10) -0.0023(11) -0.0103(11) N2 0.0229(13) 0.0160(12) 0.0161(12) 0.0024(9) -0.0041(10) -0.0073(10) N3 0.0207(13) 0.0192(13) 0.0138(12) 0.0025(9) -0.0056(10) -0.0067(10) N4 0.0198(13) 0.0205(13) 0.0165(12) 0.0017(10) -0.0054(10) -0.0068(10) N5 0.0202(13) 0.0217(13) 0.0144(12) 0.0029(10) -0.0050(10) -0.0065(10) N6 0.0190(13) 0.0221(13) 0.0171(12) 0.0046(10) -0.0050(10) -0.0084(11) N7 0.0198(13) 0.0219(13) 0.0155(12) 0.0071(10) -0.0035(10) -0.0079(10) N8 0.0174(13) 0.0252(14) 0.0189(12) 0.0078(10) -0.0050(10) -0.0072(11) N9 0.0200(13) 0.0226(14) 0.0218(13) 0.0074(11) -0.0014(11) -0.0049(11) N10 0.0195(13) 0.0251(14) 0.0201(13) 0.0056(10) -0.0048(10) -0.0085(11) N11 0.0241(14) 0.0218(14) 0.0353(16) 0.0038(12) -0.0056(12) -0.0039(11) N12 0.0284(15) 0.0250(15) 0.0438(18) 0.0072(13) -0.0066(14) -0.0087(12) O1 0.0219(11) 0.0201(11) 0.0193(10) 0.0054(8) -0.0054(9) -0.0073(9) O2 0.0186(11) 0.0292(12) 0.0191(10) -0.0009(9) -0.0019(9) -0.0073(9) O3 0.0234(11) 0.0217(11) 0.0152(10) 0.0012(8) -0.0044(9) -0.0059(9) O4 0.0188(11) 0.0260(12) 0.0208(11) 0.0024(9) -0.0035(9) -0.0085(9) O5 0.0397(14) 0.0260(13) 0.0292(13) -0.0053(10) -0.0061(11) -0.0127(11) O6 0.0320(12) 0.0226(12) 0.0254(11) 0.0040(9) -0.0079(10) -0.0155(10) O7 0.0340(13) 0.0539(17) 0.0165(11) -0.0009(10) -0.0045(10) -0.0244(12) O8 0.0254(11) 0.0328(13) 0.0170(10) 0.0012(9) -0.0046(9) -0.0156(10) O9 0.0249(12) 0.0255(12) 0.0211(11) 0.0049(9) -0.0015(9) -0.0065(9) O10 0.0198(11) 0.0298(12) 0.0212(11) 0.0080(9) -0.0066(9) -0.0098(9) O11 0.0251(13) 0.087(2) 0.0197(13) 0.0017(13) -0.0074(11) -0.0094(14) O12 0.0209(11) 0.0394(14) 0.0227(11) 0.0091(10) -0.0101(9) -0.0122(10) O13 0.0314(14) 0.0366(15) 0.0426(15) 0.0128(12) -0.0182(12) -0.0037(11) O15 0.0313(13) 0.0319(14) 0.0259(12) 0.0050(10) 0.0012(10) -0.0054(11) O16 0.0391(15) 0.0220(14) 0.0562(18) 0.0056(12) -0.0052(13) -0.0043(12) O17 0.0377(14) 0.0321(14) 0.0297(13) 0.0035(10) -0.0049(11) -0.0107(11) C38' 0.073(7) 0.018(4) 0.033(5) 0.011(4) -0.024(5) -0.008(5) C37' 0.037(5) 0.026(5) 0.021(4) 0.017(3) -0.013(3) -0.006(4) O14' 0.034(4) 0.031(5) 0.027(3) 0.022(3) -0.012(3) -0.011(4) _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 C2 1.364(5) . ? C1 C6 1.375(5) . ? C1 Cl1 1.746(3) . ? C2 C3 1.391(5) . ? C2 H2 0.9500 . ? C3 C4 1.397(5) . ? C3 H3 0.9500 . ? C4 C5 1.378(5) . ? C4 N1 1.404(4) . ? C5 C6 1.388(5) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 O1 1.229(4) . ? C7 N1 1.363(4) . ? C7 N2 1.369(4) . ? C8 C13 1.386(4) . ? C8 C9 1.402(4) . ? C8 N2 1.434(4) . ? C9 C10 1.406(4) . ? C9 C15 1.522(4) . ? C10 C11 1.398(4) . ? C10 C16 1.508(4) . ? C11 O2 1.373(4) . ? C11 C12 1.392(4) . ? C12 C13 1.381(4) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 O2 1.435(4) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 N3 1.461(4) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 N4 1.465(4) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 O3 1.215(4) . ? C17 N3 1.363(4) . ? C17 N5 1.385(4) . ? C18 O4 1.219(4) . ? C18 N4 1.371(4) . ? C18 N6 1.381(4) . ? C19 N4 1.434(4) . ? C19 N3 1.438(4) . ? C19 C20 1.546(4) . ? C19 C23 1.573(4) . ? C20 O5 1.201(4) . ? C20 O6 1.318(4) . ? C21 O6 1.469(4) . ? C21 C22 1.499(5) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 N5 1.444(4) . ? C23 N6 1.458(4) . ? C23 C24 1.548(4) . ? C24 O7 1.198(4) . ? C24 O8 1.320(4) . ? C25 O8 1.473(4) . ? C25 C26 1.497(5) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 N8 1.439(4) . ? C27 N6 1.469(4) . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? C28 N5 1.438(4) . ? C28 N7 1.452(4) . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C29 O9 1.209(4) . ? C29 N9 1.379(4) . ? C29 N7 1.389(4) . ? C30 O10 1.208(4) . ? C30 N10 1.361(4) . ? C30 N8 1.396(4) . ? C31 N8 1.448(4) . ? C31 N7 1.451(4) . ? C31 C32 1.550(4) . ? C31 C35 1.571(5) . ? C32 O11 1.193(4) . ? C32 O12 1.322(4) . ? C33 O12 1.464(4) . ? C33 C34 1.497(5) . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? C34 H34A 0.9800 . ? C34 H34B 0.9800 . ? C34 H34C 0.9800 . ? C35 N9 1.431(4) . ? C35 N10 1.438(4) . ? C35 C36 1.564(4) . ? C36 O13 1.184(4) . ? C36 O14 1.312(7) . ? C36 O14' 1.362(7) . ? C37 C38 1.464(14) . ? C37 O14 1.476(8) . ? C37 H37A 0.9900 . ? C37 H37B 0.9900 . ? C38 H38A 0.9800 . ? C38 H38B 0.9800 . ? C38 H38C 0.9800 . ? C39 N9 1.459(4) . ? C39 C41 1.515(5) . ? C39 H39A 0.9900 . ? C39 H39B 0.9900 . ? C40 N10 1.448(4) . ? C40 C42 1.525(5) . ? C40 H40A 0.9900 . ? C40 H40B 0.9900 . ? C41 C46 1.407(5) . ? C41 C42 1.410(5) . ? C42 C43 1.392(5) . ? C43 C44 1.390(5) . ? C43 N11 1.427(4) . ? C44 C45 1.386(5) . ? C44 H44 0.9500 . ? C45 C46 1.380(5) . ? C45 H45 0.9500 . ? C46 O15 1.366(4) . ? C47 O16 1.220(5) . ? C47 N11 1.363(5) . ? C47 N12 1.382(5) . ? C48 C53 1.379(6) . ? C48 C49 1.384(6) . ? C48 N12 1.405(5) . ? C49 C50 1.396(6) . ? C49 H49 0.9500 . ? C50 C51 1.357(9) . ? C50 H50 0.9500 . ? C51 C52 1.359(9) . ? C51 Cl2 1.753(4) . ? C52 C53 1.382(6) . ? C52 H52 0.9500 . ? C53 H53 0.9500 . ? C54 O15 1.434(5) . ? C54 H54A 0.9800 . ? C54 H54B 0.9800 . ? C54 H54C 0.9800 . ? C55 Cl3 1.760(6) . ? C55 Cl4 1.762(5) . ? C55 H55A 0.9900 . ? C55 H55B 0.9900 . ? C56 Cl5 1.730(6) . ? C56 Cl6 1.845(5) . ? C56 Cl6' 1.916(6) . ? C56 H56A 0.9900 . ? C56 H56B 0.9900 . ? C56 H56C 0.9900 . ? C56 H56D 0.9900 . ? C57 O17 1.411(6) . ? C57 H57A 0.9800 . ? C57 H57B 0.9800 . ? C57 H57C 0.9800 . ? Cl6 H56C 1.5788 . ? Cl6 H56D 1.6331 . ? N1 H1 0.8800 . ? N2 H2A 0.8800 . ? N11 H11 0.8800 . ? N12 H12A 0.8800 . ? O17 H17 0.89(5) . ? C38' C37' 1.524(11) . ? C38' H38D 0.9800 . ? C38' H38E 0.9800 . ? C38' H38F 0.9800 . ? C37' O14' 1.485(12) . ? C37' H37C 0.9900 . ? C37' H37D 0.9900 . ? 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 C2 C1 C6 122.0(3) . . ? C2 C1 Cl1 119.1(3) . . ? C6 C1 Cl1 118.9(3) . . ? C1 C2 C3 119.0(3) . . ? C1 C2 H2 120.5 . . ? C3 C2 H2 120.5 . . ? C2 C3 C4 120.4(3) . . ? C2 C3 H3 119.8 . . ? C4 C3 H3 119.8 . . ? C5 C4 C3 119.0(3) . . ? C5 C4 N1 122.2(3) . . ? C3 C4 N1 118.8(3) . . ? C4 C5 C6 120.8(3) . . ? C4 C5 H5 119.6 . . ? C6 C5 H5 119.6 . . ? C1 C6 C5 118.9(3) . . ? C1 C6 H6 120.6 . . ? C5 C6 H6 120.6 . . ? O1 C7 N1 122.6(3) . . ? O1 C7 N2 122.7(3) . . ? N1 C7 N2 114.6(3) . . ? C13 C8 C9 119.8(3) . . ? C13 C8 N2 117.8(3) . . ? C9 C8 N2 122.5(3) . . ? C8 C9 C10 119.1(3) . . ? C8 C9 C15 120.1(3) . . ? C10 C9 C15 120.8(3) . . ? C11 C10 C9 119.8(3) . . ? C11 C10 C16 118.8(3) . . ? C9 C10 C16 121.4(3) . . ? O2 C11 C12 123.0(3) . . ? O2 C11 C10 116.4(3) . . ? C12 C11 C10 120.6(3) . . ? C13 C12 C11 119.0(3) . . ? C13 C12 H12 120.5 . . ? C11 C12 H12 120.5 . . ? C12 C13 C8 121.7(3) . . ? C12 C13 H13 119.2 . . ? C8 C13 H13 119.2 . . ? O2 C14 H14A 109.5 . . ? O2 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? O2 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? N3 C15 C9 113.6(2) . . ? N3 C15 H15A 108.8 . . ? C9 C15 H15A 108.8 . . ? N3 C15 H15B 108.8 . . ? C9 C15 H15B 108.8 . . ? H15A C15 H15B 107.7 . . ? N4 C16 C10 115.0(2) . . ? N4 C16 H16A 108.5 . . ? C10 C16 H16A 108.5 . . ? N4 C16 H16B 108.5 . . ? C10 C16 H16B 108.5 . . ? H16A C16 H16B 107.5 . . ? O3 C17 N3 127.3(3) . . ? O3 C17 N5 125.1(3) . . ? N3 C17 N5 107.6(2) . . ? O4 C18 N4 125.6(3) . . ? O4 C18 N6 126.1(3) . . ? N4 C18 N6 108.3(3) . . ? N4 C19 N3 113.5(2) . . ? N4 C19 C20 109.9(2) . . ? N3 C19 C20 114.4(2) . . ? N4 C19 C23 103.4(2) . . ? N3 C19 C23 102.3(2) . . ? C20 C19 C23 112.6(2) . . ? O5 C20 O6 126.8(3) . . ? O5 C20 C19 121.0(3) . . ? O6 C20 C19 112.2(3) . . ? O6 C21 C22 106.9(3) . . ? O6 C21 H21A 110.3 . . ? C22 C21 H21A 110.3 . . ? O6 C21 H21B 110.3 . . ? C22 C21 H21B 110.3 . . ? H21A C21 H21B 108.6 . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? N5 C23 N6 115.6(3) . . ? N5 C23 C24 111.9(2) . . ? N6 C23 C24 111.5(2) . . ? N5 C23 C19 102.0(2) . . ? N6 C23 C19 101.6(2) . . ? C24 C23 C19 113.5(2) . . ? O7 C24 O8 126.5(3) . . ? O7 C24 C23 123.3(3) . . ? O8 C24 C23 110.2(2) . . ? O8 C25 C26 109.9(3) . . ? O8 C25 H25A 109.7 . . ? C26 C25 H25A 109.7 . . ? O8 C25 H25B 109.7 . . ? C26 C25 H25B 109.7 . . ? H25A C25 H25B 108.2 . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? N8 C27 N6 114.5(2) . . ? N8 C27 H27A 108.6 . . ? N6 C27 H27A 108.6 . . ? N8 C27 H27B 108.6 . . ? N6 C27 H27B 108.6 . . ? H27A C27 H27B 107.6 . . ? N5 C28 N7 114.4(2) . . ? N5 C28 H28A 108.7 . . ? N7 C28 H28A 108.7 . . ? N5 C28 H28B 108.7 . . ? N7 C28 H28B 108.7 . . ? H28A C28 H28B 107.6 . . ? O9 C29 N9 126.1(3) . . ? O9 C29 N7 126.1(3) . . ? N9 C29 N7 107.9(3) . . ? O10 C30 N10 127.4(3) . . ? O10 C30 N8 125.1(3) . . ? N10 C30 N8 107.6(3) . . ? N8 C31 N7 115.6(2) . . ? N8 C31 C32 111.5(3) . . ? N7 C31 C32 113.8(3) . . ? N8 C31 C35 102.1(2) . . ? N7 C31 C35 101.7(2) . . ? C32 C31 C35 110.9(2) . . ? O11 C32 O12 126.3(3) . . ? O11 C32 C31 122.8(3) . . ? O12 C32 C31 110.8(3) . . ? O12 C33 C34 106.3(3) . . ? O12 C33 H33A 110.5 . . ? C34 C33 H33A 110.5 . . ? O12 C33 H33B 110.5 . . ? C34 C33 H33B 110.5 . . ? H33A C33 H33B 108.7 . . ? C33 C34 H34A 109.5 . . ? C33 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C33 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? N9 C35 N10 114.2(3) . . ? N9 C35 C36 110.7(3) . . ? N10 C35 C36 112.4(2) . . ? N9 C35 C31 104.1(2) . . ? N10 C35 C31 103.0(2) . . ? C36 C35 C31 111.9(3) . . ? O13 C36 O14 122.5(4) . . ? O13 C36 O14' 129.7(5) . . ? O14 C36 O14' 24.9(4) . . ? O13 C36 C35 122.5(3) . . ? O14 C36 C35 114.2(4) . . ? O14' C36 C35 105.6(4) . . ? C38 C37 O14 105.8(7) . . ? C38 C37 H37A 110.6 . . ? O14 C37 H37A 110.6 . . ? C38 C37 H37B 110.6 . . ? O14 C37 H37B 110.6 . . ? H37A C37 H37B 108.7 . . ? C36 O14 C37 117.1(7) . . ? N9 C39 C41 115.3(3) . . ? N9 C39 H39A 108.5 . . ? C41 C39 H39A 108.5 . . ? N9 C39 H39B 108.5 . . ? C41 C39 H39B 108.5 . . ? H39A C39 H39B 107.5 . . ? N10 C40 C42 113.4(2) . . ? N10 C40 H40A 108.9 . . ? C42 C40 H40A 108.9 . . ? N10 C40 H40B 108.9 . . ? C42 C40 H40B 108.9 . . ? H40A C40 H40B 107.7 . . ? C46 C41 C42 118.7(3) . . ? C46 C41 C39 119.1(3) . . ? C42 C41 C39 122.2(3) . . ? C43 C42 C41 119.5(3) . . ? C43 C42 C40 120.2(3) . . ? C41 C42 C40 120.2(3) . . ? C44 C43 C42 120.7(3) . . ? C44 C43 N11 118.5(3) . . ? C42 C43 N11 120.7(3) . . ? C45 C44 C43 120.2(3) . . ? C45 C44 H44 119.9 . . ? C43 C44 H44 119.9 . . ? C46 C45 C44 119.8(3) . . ? C46 C45 H45 120.1 . . ? C44 C45 H45 120.1 . . ? O15 C46 C45 123.4(3) . . ? O15 C46 C41 115.5(3) . . ? C45 C46 C41 121.1(3) . . ? O16 C47 N11 124.0(3) . . ? O16 C47 N12 123.8(3) . . ? N11 C47 N12 112.2(3) . . ? C53 C48 C49 118.8(4) . . ? C53 C48 N12 116.8(4) . . ? C49 C48 N12 124.4(4) . . ? C48 C49 C50 119.3(5) . . ? C48 C49 H49 120.4 . . ? C50 C49 H49 120.4 . . ? C51 C50 C49 120.2(5) . . ? C51 C50 H50 119.9 . . ? C49 C50 H50 119.9 . . ? C50 C51 C52 121.4(4) . . ? C50 C51 Cl2 119.3(5) . . ? C52 C51 Cl2 119.3(5) . . ? C51 C52 C53 118.8(5) . . ? C51 C52 H52 120.6 . . ? C53 C52 H52 120.6 . . ? C48 C53 C52 121.5(5) . . ? C48 C53 H53 119.2 . . ? C52 C53 H53 119.2 . . ? O15 C54 H54A 109.5 . . ? O15 C54 H54B 109.5 . . ? H54A C54 H54B 109.5 . . ? O15 C54 H54C 109.5 . . ? H54A C54 H54C 109.5 . . ? H54B C54 H54C 109.5 . . ? Cl3 C55 Cl4 111.0(3) . . ? Cl3 C55 H55A 109.4 . . ? Cl4 C55 H55A 109.4 . . ? Cl3 C55 H55B 109.4 . . ? Cl4 C55 H55B 109.4 . . ? H55A C55 H55B 108.0 . . ? Cl5 C56 Cl6 103.7(3) . . ? Cl5 C56 Cl6' 93.7(3) . . ? Cl6 C56 Cl6' 162.6(4) . . ? Cl5 C56 H56A 111.0 . . ? Cl6 C56 H56A 111.0 . . ? Cl6' C56 H56A 62.4 . . ? Cl5 C56 H56B 111.0 . . ? Cl6 C56 H56B 111.0 . . ? Cl6' C56 H56B 60.4 . . ? H56A C56 H56B 109.0 . . ? Cl5 C56 H56C 113.9 . . ? Cl6 C56 H56C 58.8 . . ? Cl6' C56 H56C 113.1 . . ? H56A C56 H56C 135.1 . . ? H56B C56 H56C 53.0 . . ? Cl5 C56 H56D 113.0 . . ? Cl6 C56 H56D 62.0 . . ? Cl6' C56 H56D 112.2 . . ? H56A C56 H56D 50.0 . . ? H56B C56 H56D 135.8 . . ? H56C C56 H56D 110.2 . . ? O17 C57 H57A 109.5 . . ? O17 C57 H57B 109.5 . . ? H57A C57 H57B 109.5 . . ? O17 C57 H57C 109.5 . . ? H57A C57 H57C 109.5 . . ? H57B C57 H57C 109.5 . . ? C56 Cl6 H56C 32.5 . . ? C56 Cl6 H56D 32.4 . . ? H56C Cl6 H56D 60.7 . . ? C7 N1 C4 122.1(3) . . ? C7 N1 H1 118.9 . . ? C4 N1 H1 118.9 . . ? C7 N2 C8 120.4(3) . . ? C7 N2 H2A 119.8 . . ? C8 N2 H2A 119.8 . . ? C17 N3 C19 112.6(2) . . ? C17 N3 C15 123.0(2) . . ? C19 N3 C15 124.0(2) . . ? C18 N4 C19 111.6(2) . . ? C18 N4 C16 121.9(2) . . ? C19 N4 C16 119.2(2) . . ? C17 N5 C28 121.5(3) . . ? C17 N5 C23 112.3(2) . . ? C28 N5 C23 126.1(2) . . ? C18 N6 C23 112.1(2) . . ? C18 N6 C27 120.7(2) . . ? C23 N6 C27 125.3(2) . . ? C29 N7 C31 112.6(2) . . ? C29 N7 C28 120.5(2) . . ? C31 N7 C28 124.4(3) . . ? C30 N8 C27 122.2(3) . . ? C30 N8 C31 112.3(3) . . ? C27 N8 C31 125.5(3) . . ? C29 N9 C35 111.8(3) . . ? C29 N9 C39 121.5(3) . . ? C35 N9 C39 121.5(3) . . ? C30 N10 C35 112.9(3) . . ? C30 N10 C40 125.0(3) . . ? C35 N10 C40 121.8(3) . . ? C47 N11 C43 121.9(3) . . ? C47 N11 H11 119.0 . . ? C43 N11 H11 119.0 . . ? C47 N12 C48 126.7(3) . . ? C47 N12 H12A 116.6 . . ? C48 N12 H12A 116.6 . . ? C11 O2 C14 116.9(2) . . ? C20 O6 C21 115.9(3) . . ? C24 O8 C25 115.8(2) . . ? C32 O12 C33 115.6(2) . . ? C46 O15 C54 116.8(3) . . ? C57 O17 H17 98(3) . . ? C37' C38' H38D 109.5 . . ? C37' C38' H38E 109.5 . . ? H38D C38' H38E 109.5 . . ? C37' C38' H38F 109.5 . . ? H38D C38' H38F 109.5 . . ? H38E C38' H38F 109.5 . . ? O14' C37' C38' 111.9(7) . . ? O14' C37' H37C 109.2 . . ? C38' C37' H37C 109.2 . . ? O14' C37' H37D 109.2 . . ? C38' C37' H37D 109.2 . . ? H37C C37' H37D 107.9 . . ? C36 O14' C37' 115.5(7) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -0.4(6) . . . . ? Cl1 C1 C2 C3 -179.2(3) . . . . ? C1 C2 C3 C4 0.3(6) . . . . ? C2 C3 C4 C5 -0.6(5) . . . . ? C2 C3 C4 N1 179.8(3) . . . . ? C3 C4 C5 C6 0.9(6) . . . . ? N1 C4 C5 C6 -179.5(3) . . . . ? C2 C1 C6 C5 0.7(6) . . . . ? Cl1 C1 C6 C5 179.5(3) . . . . ? C4 C5 C6 C1 -0.9(6) . . . . ? C13 C8 C9 C10 0.5(4) . . . . ? N2 C8 C9 C10 178.5(3) . . . . ? C13 C8 C9 C15 179.8(3) . . . . ? N2 C8 C9 C15 -2.1(4) . . . . ? C8 C9 C10 C11 -1.6(4) . . . . ? C15 C9 C10 C11 179.0(3) . . . . ? C8 C9 C10 C16 177.9(3) . . . . ? C15 C9 C10 C16 -1.4(4) . . . . ? C9 C10 C11 O2 -178.6(2) . . . . ? C16 C10 C11 O2 1.8(4) . . . . ? C9 C10 C11 C12 1.7(4) . . . . ? C16 C10 C11 C12 -177.8(3) . . . . ? O2 C11 C12 C13 179.7(3) . . . . ? C10 C11 C12 C13 -0.7(4) . . . . ? C11 C12 C13 C8 -0.5(4) . . . . ? C9 C8 C13 C12 0.6(4) . . . . ? N2 C8 C13 C12 -177.5(3) . . . . ? C8 C9 C15 N3 125.1(3) . . . . ? C10 C9 C15 N3 -55.6(4) . . . . ? C11 C10 C16 N4 -119.1(3) . . . . ? C9 C10 C16 N4 61.4(4) . . . . ? N4 C19 C20 O5 -40.4(4) . . . . ? N3 C19 C20 O5 -169.4(3) . . . . ? C23 C19 C20 O5 74.4(4) . . . . ? N4 C19 C20 O6 141.7(3) . . . . ? N3 C19 C20 O6 12.7(4) . . . . ? C23 C19 C20 O6 -103.6(3) . . . . ? N4 C19 C23 N5 -134.9(2) . . . . ? N3 C19 C23 N5 -16.8(3) . . . . ? C20 C19 C23 N5 106.5(3) . . . . ? N4 C19 C23 N6 -15.3(3) . . . . ? N3 C19 C23 N6 102.8(2) . . . . ? C20 C19 C23 N6 -133.9(3) . . . . ? N4 C19 C23 C24 104.5(3) . . . . ? N3 C19 C23 C24 -137.3(2) . . . . ? C20 C19 C23 C24 -14.1(3) . . . . ? N5 C23 C24 O7 140.5(3) . . . . ? N6 C23 C24 O7 9.2(4) . . . . ? C19 C23 C24 O7 -104.8(4) . . . . ? N5 C23 C24 O8 -40.9(3) . . . . ? N6 C23 C24 O8 -172.2(3) . . . . ? C19 C23 C24 O8 73.8(3) . . . . ? N8 C31 C32 O11 -26.3(5) . . . . ? N7 C31 C32 O11 -159.2(3) . . . . ? C35 C31 C32 O11 86.9(4) . . . . ? N8 C31 C32 O12 157.5(3) . . . . ? N7 C31 C32 O12 24.5(4) . . . . ? C35 C31 C32 O12 -89.4(3) . . . . ? N8 C31 C35 N9 -132.8(2) . . . . ? N7 C31 C35 N9 -13.0(3) . . . . ? C32 C31 C35 N9 108.3(3) . . . . ? N8 C31 C35 N10 -13.3(3) . . . . ? N7 C31 C35 N10 106.4(2) . . . . ? C32 C31 C35 N10 -132.3(3) . . . . ? N8 C31 C35 C36 107.6(3) . . . . ? N7 C31 C35 C36 -132.6(3) . . . . ? C32 C31 C35 C36 -11.3(3) . . . . ? N9 C35 C36 O13 -32.1(5) . . . . ? N10 C35 C36 O13 -161.1(3) . . . . ? C31 C35 C36 O13 83.5(4) . . . . ? N9 C35 C36 O14 138.2(5) . . . . ? N10 C35 C36 O14 9.2(6) . . . . ? C31 C35 C36 O14 -106.1(5) . . . . ? N9 C35 C36 O14' 163.1(5) . . . . ? N10 C35 C36 O14' 34.1(5) . . . . ? C31 C35 C36 O14' -81.2(5) . . . . ? O13 C36 O14 C37 -12.9(11) . . . . ? O14' C36 O14 C37 102.3(19) . . . . ? C35 C36 O14 C37 176.8(7) . . . . ? C38 C37 O14 C36 -177.5(9) . . . . ? N9 C39 C41 C46 -124.1(3) . . . . ? N9 C39 C41 C42 58.1(4) . . . . ? C46 C41 C42 C43 -1.4(4) . . . . ? C39 C41 C42 C43 176.4(3) . . . . ? C46 C41 C42 C40 -178.5(3) . . . . ? C39 C41 C42 C40 -0.7(4) . . . . ? N10 C40 C42 C43 124.9(3) . . . . ? N10 C40 C42 C41 -58.0(4) . . . . ? C41 C42 C43 C44 -0.2(5) . . . . ? C40 C42 C43 C44 176.9(3) . . . . ? C41 C42 C43 N11 178.8(3) . . . . ? C40 C42 C43 N11 -4.1(4) . . . . ? C42 C43 C44 C45 1.4(5) . . . . ? N11 C43 C44 C45 -177.7(3) . . . . ? C43 C44 C45 C46 -0.9(5) . . . . ? C44 C45 C46 O15 -179.2(3) . . . . ? C44 C45 C46 C41 -0.8(5) . . . . ? C42 C41 C46 O15 -179.5(3) . . . . ? C39 C41 C46 O15 2.6(4) . . . . ? C42 C41 C46 C45 2.0(5) . . . . ? C39 C41 C46 C45 -175.9(3) . . . . ? C53 C48 C49 C50 -0.1(7) . . . . ? N12 C48 C49 C50 -179.6(4) . . . . ? C48 C49 C50 C51 -1.6(7) . . . . ? C49 C50 C51 C52 2.7(8) . . . . ? C49 C50 C51 Cl2 -178.8(4) . . . . ? C50 C51 C52 C53 -2.2(8) . . . . ? Cl2 C51 C52 C53 179.4(4) . . . . ? C49 C48 C53 C52 0.6(8) . . . . ? N12 C48 C53 C52 -179.8(5) . . . . ? C51 C52 C53 C48 0.5(9) . . . . ? O1 C7 N1 C4 5.9(5) . . . . ? N2 C7 N1 C4 -178.3(3) . . . . ? C5 C4 N1 C7 42.3(5) . . . . ? C3 C4 N1 C7 -138.1(3) . . . . ? O1 C7 N2 C8 -13.3(4) . . . . ? N1 C7 N2 C8 171.0(3) . . . . ? C13 C8 N2 C7 -115.8(3) . . . . ? C9 C8 N2 C7 66.1(4) . . . . ? O3 C17 N3 C19 170.2(3) . . . . ? N5 C17 N3 C19 -9.9(3) . . . . ? O3 C17 N3 C15 -2.9(5) . . . . ? N5 C17 N3 C15 177.0(2) . . . . ? N4 C19 N3 C17 127.7(3) . . . . ? C20 C19 N3 C17 -105.2(3) . . . . ? C23 C19 N3 C17 16.9(3) . . . . ? N4 C19 N3 C15 -59.3(4) . . . . ? C20 C19 N3 C15 67.9(4) . . . . ? C23 C19 N3 C15 -170.0(2) . . . . ? C9 C15 N3 C17 -112.4(3) . . . . ? C9 C15 N3 C19 75.3(3) . . . . ? O4 C18 N4 C19 167.7(3) . . . . ? N6 C18 N4 C19 -11.7(3) . . . . ? O4 C18 N4 C16 17.8(5) . . . . ? N6 C18 N4 C16 -161.7(3) . . . . ? N3 C19 N4 C18 -92.9(3) . . . . ? C20 C19 N4 C18 137.6(3) . . . . ? C23 C19 N4 C18 17.1(3) . . . . ? N3 C19 N4 C16 57.9(3) . . . . ? C20 C19 N4 C16 -71.5(3) . . . . ? C23 C19 N4 C16 168.0(2) . . . . ? C10 C16 N4 C18 69.9(4) . . . . ? C10 C16 N4 C19 -77.9(3) . . . . ? O3 C17 N5 C28 0.1(4) . . . . ? N3 C17 N5 C28 -179.8(2) . . . . ? O3 C17 N5 C23 177.2(3) . . . . ? N3 C17 N5 C23 -2.7(3) . . . . ? N7 C28 N5 C17 93.7(3) . . . . ? N7 C28 N5 C23 -83.0(4) . . . . ? N6 C23 N5 C17 -96.7(3) . . . . ? C24 C23 N5 C17 134.1(3) . . . . ? C19 C23 N5 C17 12.5(3) . . . . ? N6 C23 N5 C28 80.2(4) . . . . ? C24 C23 N5 C28 -48.9(4) . . . . ? C19 C23 N5 C28 -170.6(3) . . . . ? O4 C18 N6 C23 -179.1(3) . . . . ? N4 C18 N6 C23 0.4(3) . . . . ? O4 C18 N6 C27 15.6(5) . . . . ? N4 C18 N6 C27 -164.9(3) . . . . ? N5 C23 N6 C18 119.0(3) . . . . ? C24 C23 N6 C18 -111.6(3) . . . . ? C19 C23 N6 C18 9.5(3) . . . . ? N5 C23 N6 C27 -76.5(4) . . . . ? C24 C23 N6 C27 52.9(4) . . . . ? C19 C23 N6 C27 174.1(3) . . . . ? N8 C27 N6 C18 -118.1(3) . . . . ? N8 C27 N6 C23 78.7(4) . . . . ? O9 C29 N7 C31 177.1(3) . . . . ? N9 C29 N7 C31 -1.9(3) . . . . ? O9 C29 N7 C28 14.2(5) . . . . ? N9 C29 N7 C28 -164.8(3) . . . . ? N8 C31 N7 C29 119.1(3) . . . . ? C32 C31 N7 C29 -109.9(3) . . . . ? C35 C31 N7 C29 9.4(3) . . . . ? N8 C31 N7 C28 -78.8(4) . . . . ? C32 C31 N7 C28 52.2(4) . . . . ? C35 C31 N7 C28 171.5(3) . . . . ? N5 C28 N7 C29 -118.9(3) . . . . ? N5 C28 N7 C31 80.4(3) . . . . ? O10 C30 N8 C27 -2.3(4) . . . . ? N10 C30 N8 C27 177.5(2) . . . . ? O10 C30 N8 C31 179.3(3) . . . . ? N10 C30 N8 C31 -0.9(3) . . . . ? N6 C27 N8 C30 99.8(3) . . . . ? N6 C27 N8 C31 -82.0(3) . . . . ? N7 C31 N8 C30 -100.3(3) . . . . ? C32 C31 N8 C30 127.7(3) . . . . ? C35 C31 N8 C30 9.1(3) . . . . ? N7 C31 N8 C27 81.4(4) . . . . ? C32 C31 N8 C27 -50.7(4) . . . . ? C35 C31 N8 C27 -169.2(3) . . . . ? O9 C29 N9 C35 173.3(3) . . . . ? N7 C29 N9 C35 -7.7(3) . . . . ? O9 C29 N9 C39 18.5(5) . . . . ? N7 C29 N9 C39 -162.5(3) . . . . ? N10 C35 N9 C29 -98.4(3) . . . . ? C36 C35 N9 C29 133.5(3) . . . . ? C31 C35 N9 C29 13.2(3) . . . . ? N10 C35 N9 C39 56.5(4) . . . . ? C36 C35 N9 C39 -71.6(4) . . . . ? C31 C35 N9 C39 168.0(3) . . . . ? C41 C39 N9 C29 79.1(4) . . . . ? C41 C39 N9 C35 -73.3(4) . . . . ? O10 C30 N10 C35 170.8(3) . . . . ? N8 C30 N10 C35 -9.0(3) . . . . ? O10 C30 N10 C40 -2.2(5) . . . . ? N8 C30 N10 C40 178.0(3) . . . . ? N9 C35 N10 C30 126.5(3) . . . . ? C36 C35 N10 C30 -106.4(3) . . . . ? C31 C35 N10 C30 14.2(3) . . . . ? N9 C35 N10 C40 -60.3(4) . . . . ? C36 C35 N10 C40 66.8(4) . . . . ? C31 C35 N10 C40 -172.6(2) . . . . ? C42 C40 N10 C30 -109.1(3) . . . . ? C42 C40 N10 C35 78.6(4) . . . . ? O16 C47 N11 C43 -0.6(6) . . . . ? N12 C47 N11 C43 179.9(3) . . . . ? C44 C43 N11 C47 -68.4(4) . . . . ? C42 C43 N11 C47 112.5(4) . . . . ? O16 C47 N12 C48 -7.7(6) . . . . ? N11 C47 N12 C48 171.8(3) . . . . ? C53 C48 N12 C47 176.0(4) . . . . ? C49 C48 N12 C47 -4.5(6) . . . . ? C12 C11 O2 C14 1.1(4) . . . . ? C10 C11 O2 C14 -178.6(3) . . . . ? O5 C20 O6 C21 -3.3(5) . . . . ? C19 C20 O6 C21 174.5(3) . . . . ? C22 C21 O6 C20 172.4(3) . . . . ? O7 C24 O8 C25 -0.8(5) . . . . ? C23 C24 O8 C25 -179.3(3) . . . . ? C26 C25 O8 C24 -80.7(3) . . . . ? O11 C32 O12 C33 -5.0(5) . . . . ? C31 C32 O12 C33 171.1(3) . . . . ? C34 C33 O12 C32 175.8(3) . . . . ? C45 C46 O15 C54 -7.3(5) . . . . ? C41 C46 O15 C54 174.2(3) . . . . ? O13 C36 O14' C37' 10.3(10) . . . . ? O14 C36 O14' C37' -72.3(14) . . . . ? C35 C36 O14' C37' 173.5(6) . . . . ? C38' C37' O14' C36 90.9(10) . . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 1.436 _refine_diff_density_min -1.509 _refine_diff_density_rms 0.094 # start Validation Reply Form _vrf_PLAT220_100401dm ; PROBLEM: Large Non-Solvent C Ueq(max)/Ueq(min) ... 4.18 Ratio RESPONSE: The problem should be induced by the disorder. ; # end Validation Reply Form #===END data_081225cm _database_code_depnum_ccdc_archive 'CCDC 782747' #TrackingRef '- CIFs Combined CC.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C37 H33 F5 N6 O10, 3(C H Cl3)' _chemical_formula_sum 'C40 H36 Cl9 F5 N6 O10' _chemical_formula_weight 1174.80 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' F F 0.0171 0.0103 '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 10.5648(10) _cell_length_b 15.5841(14) _cell_length_c 16.8119(15) _cell_angle_alpha 116.7660(10) _cell_angle_beta 97.158(2) _cell_angle_gamma 90.808(2) _cell_volume 2444.4(4) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 7642 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 28.3 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.596 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1192 _exptl_absorpt_coefficient_mu 0.596 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8901 _exptl_absorpt_correction_T_max 0.9428 _exptl_absorpt_process_details 'SADABS, (Sheldrick,1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 28452 _diffrn_reflns_av_R_equivalents 0.0845 _diffrn_reflns_av_sigmaI/netI 0.0754 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.37 _diffrn_reflns_theta_max 27.50 _reflns_number_total 10910 _reflns_number_gt 7029 _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 '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^)+(0.0847P)^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 10910 _refine_ls_number_parameters 662 _refine_ls_number_restraints 9 _refine_ls_R_factor_all 0.0834 _refine_ls_R_factor_gt 0.0567 _refine_ls_wR_factor_ref 0.1534 _refine_ls_wR_factor_gt 0.1414 _refine_ls_goodness_of_fit_ref 0.950 _refine_ls_restrained_S_all 0.955 _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 C1 C -0.2946(3) 1.2395(2) 0.35267(19) 0.0413(7) Uani 1 1 d . . . H1A H -0.3770 1.2671 0.3507 0.062 Uiso 1 1 calc R . . H1B H -0.2776 1.1993 0.2911 0.062 Uiso 1 1 calc R . . H1C H -0.2265 1.2916 0.3846 0.062 Uiso 1 1 calc R . . C2 C -0.2987(2) 1.17872(18) 0.40129(17) 0.0299(5) Uani 1 1 d . . . C3 C -0.2210(2) 1.02895(17) 0.40045(15) 0.0254(5) Uani 1 1 d . . . C4 C -0.1822(2) 1.06321(18) 0.49231(15) 0.0283(5) Uani 1 1 d . . . H4 H -0.1752 1.1306 0.5310 0.034 Uiso 1 1 calc R . . C5 C -0.1536(2) 1.00015(18) 0.52784(15) 0.0294(5) Uani 1 1 d . . . H5 H -0.1315 1.0240 0.5911 0.035 Uiso 1 1 calc R . . C6 C -0.1572(2) 0.90146(17) 0.47096(15) 0.0261(5) Uani 1 1 d . . . C7 C -0.1955(2) 0.86634(16) 0.37842(15) 0.0233(5) Uani 1 1 d . . . C8 C -0.2321(2) 0.92974(16) 0.34296(15) 0.0233(5) Uani 1 1 d . . . C9 C -0.0939(3) 0.8668(2) 0.59379(16) 0.0377(6) Uani 1 1 d . . . H9A H -0.0233 0.9174 0.6192 0.057 Uiso 1 1 calc R . . H9B H -0.0691 0.8126 0.6052 0.057 Uiso 1 1 calc R . . H9C H -0.1697 0.8927 0.6220 0.057 Uiso 1 1 calc R . . C10 C -0.2820(2) 0.88940(16) 0.24371(14) 0.0228(5) Uani 1 1 d . . . H10A H -0.3537 0.8404 0.2283 0.027 Uiso 1 1 calc R . . H10B H -0.3164 0.9421 0.2320 0.027 Uiso 1 1 calc R . . C11 C -0.1935(2) 0.75954(16) 0.31646(14) 0.0240(5) Uani 1 1 d . . . H11A H -0.1648 0.7260 0.3526 0.029 Uiso 1 1 calc R . . H11B H -0.2811 0.7324 0.2851 0.029 Uiso 1 1 calc R . . C12 C -0.0841(2) 0.90333(17) 0.18481(14) 0.0235(5) Uani 1 1 d . . . C13 C 0.0180(2) 0.72838(15) 0.26332(14) 0.0213(5) Uani 1 1 d . . . C14 C -0.1461(2) 0.75099(16) 0.16831(14) 0.0203(5) Uani 1 1 d . . . C15 C -0.2518(2) 0.67134(17) 0.10563(15) 0.0241(5) Uani 1 1 d . A . C17 C -0.3797(9) 0.4768(7) 0.0934(6) 0.048(3) Uani 0.480(18) 1 d PD A 1 H17A H -0.3241 0.4641 0.1375 0.073 Uiso 0.480(18) 1 calc PR A 1 H17B H -0.4395 0.4202 0.0556 0.073 Uiso 0.480(18) 1 calc PR A 1 H17C H -0.4278 0.5326 0.1250 0.073 Uiso 0.480(18) 1 calc PR A 1 C16 C -0.2989(9) 0.4976(5) 0.0351(6) 0.029(2) Uani 0.480(18) 1 d PD A 1 H16A H -0.2450 0.4439 0.0059 0.035 Uiso 0.480(18) 1 calc PR A 1 H16B H -0.3536 0.5070 -0.0121 0.035 Uiso 0.480(18) 1 calc PR A 1 C16' C -0.3314(10) 0.5147(7) 0.0566(10) 0.054(3) Uani 0.520(18) 1 d PD A 2 H16C H -0.4114 0.5480 0.0656 0.065 Uiso 0.520(18) 1 calc PR A 2 H16D H -0.3307 0.4764 -0.0089 0.065 Uiso 0.520(18) 1 calc PR A 2 C17' C -0.3261(11) 0.4506(6) 0.0998(6) 0.059(3) Uani 0.520(18) 1 d PD A 2 H17D H -0.2416 0.4252 0.0986 0.089 Uiso 0.520(18) 1 calc PR A 2 H17E H -0.3920 0.3969 0.0671 0.089 Uiso 0.520(18) 1 calc PR A 2 H17F H -0.3411 0.4869 0.1624 0.089 Uiso 0.520(18) 1 calc PR A 2 C18 C -0.0150(2) 0.74694(16) 0.13232(14) 0.0227(5) Uani 1 1 d . . . C19 C -0.0111(2) 0.68064(18) 0.03206(16) 0.0315(6) Uani 1 1 d . . . C20 C -0.1218(3) 0.6192(2) -0.11566(16) 0.0401(7) Uani 1 1 d . . . H20A H -0.0430 0.6338 -0.1351 0.048 Uiso 1 1 calc R . . H20B H -0.1958 0.6342 -0.1482 0.048 Uiso 1 1 calc R . . C21 C -0.1337(3) 0.5148(2) -0.13904(18) 0.0513(8) Uani 1 1 d . . . H21A H -0.0552 0.4980 -0.1135 0.077 Uiso 1 1 calc R . . H21B H -0.1472 0.4762 -0.2047 0.077 Uiso 1 1 calc R . . H21C H -0.2067 0.5017 -0.1143 0.077 Uiso 1 1 calc R . . C22 C 0.1363(2) 0.88098(18) 0.14198(15) 0.0267(5) Uani 1 1 d . . . H22A H 0.1264 0.9410 0.1361 0.032 Uiso 1 1 calc R . . H22B H 0.1645 0.8324 0.0860 0.032 Uiso 1 1 calc R . . C23 C 0.2099(2) 0.72846(16) 0.19622(16) 0.0252(5) Uani 1 1 d . . . H23A H 0.2333 0.7007 0.1348 0.030 Uiso 1 1 calc R . . H23B H 0.2469 0.6898 0.2253 0.030 Uiso 1 1 calc R . . C24 C 0.2400(2) 0.90089(17) 0.22097(15) 0.0248(5) Uani 1 1 d . . . C25 C 0.2713(2) 0.83090(16) 0.24886(15) 0.0239(5) Uani 1 1 d . . . C26 C 0.3677(2) 0.85388(18) 0.32235(16) 0.0273(5) Uani 1 1 d . . . C27 C 0.4344(2) 0.94334(19) 0.36416(16) 0.0323(6) Uani 1 1 d . . . H27 H 0.4991 0.9584 0.4141 0.039 Uiso 1 1 calc R . . C28 C 0.4081(2) 1.01171(18) 0.33418(16) 0.0324(6) Uani 1 1 d . . . H28 H 0.4564 1.0724 0.3622 0.039 Uiso 1 1 calc R . . C29 C 0.3115(2) 0.99119(17) 0.26346(16) 0.0283(5) Uani 1 1 d . . . C30 C 0.3689(3) 1.1322(2) 0.2506(2) 0.0509(8) Uani 1 1 d . . . H30A H 0.3780 1.1756 0.3154 0.076 Uiso 1 1 calc R . . H30B H 0.3386 1.1673 0.2169 0.076 Uiso 1 1 calc R . . H30C H 0.4520 1.1081 0.2346 0.076 Uiso 1 1 calc R . . C31 C 0.4689(2) 0.71162(19) 0.30982(16) 0.0317(6) Uani 1 1 d . . . C32 C 0.5079(2) 0.65063(19) 0.35609(17) 0.0320(6) Uani 1 1 d . . . C33 C 0.5772(2) 0.6876(2) 0.44116(17) 0.0345(6) Uani 1 1 d . . . C34 C 0.6183(3) 0.6294(2) 0.47990(18) 0.0453(7) Uani 1 1 d . . . C35 C 0.5892(3) 0.5321(2) 0.4331(2) 0.0533(8) Uani 1 1 d . . . C36 C 0.5209(3) 0.4927(2) 0.3488(2) 0.0542(8) Uani 1 1 d . . . C37 C 0.4823(3) 0.5513(2) 0.31088(18) 0.0418(7) Uani 1 1 d . . . C38 C 0.5688(3) 0.8409(2) 0.01470(18) 0.0417(7) Uani 1 1 d . . . H38 H 0.6294 0.8048 0.0366 0.050 Uiso 1 1 calc R . . C39 C 0.9810(3) 0.1479(2) 0.1483(2) 0.0502(8) Uani 1 1 d . . . H39 H 0.9695 0.0906 0.1594 0.060 Uiso 1 1 calc R . . C40 C 1.0140(3) 0.5746(3) 0.3900(2) 0.0591(9) Uani 1 1 d . . . H40 H 1.0347 0.6338 0.3836 0.071 Uiso 1 1 calc R . . Cl1 Cl 0.64878(8) 0.95009(6) 0.03769(6) 0.0632(2) Uani 1 1 d . . . Cl2 Cl 0.43750(8) 0.86025(8) 0.07191(6) 0.0718(3) Uani 1 1 d . . . Cl3 Cl 0.52262(11) 0.77031(7) -0.10128(5) 0.0787(3) Uani 1 1 d . . . Cl4 Cl 1.04402(10) 0.24719(7) 0.25060(5) 0.0676(3) Uani 1 1 d . . . Cl5 Cl 0.83132(9) 0.17074(8) 0.10651(7) 0.0742(3) Uani 1 1 d . . . Cl6 Cl 1.08695(9) 0.12239(6) 0.06943(6) 0.0624(2) Uani 1 1 d . . . Cl7 Cl 0.89046(11) 0.50548(10) 0.30485(9) 0.1040(4) Uani 1 1 d . . . Cl8 Cl 1.15150(9) 0.51073(9) 0.37948(7) 0.0810(3) Uani 1 1 d . . . Cl9 Cl 0.96613(12) 0.61027(8) 0.49499(7) 0.0905(4) Uani 1 1 d . . . F1 F 0.60811(14) 0.78304(11) 0.48850(10) 0.0416(4) Uani 1 1 d . . . F2 F 0.68536(18) 0.66842(14) 0.56327(11) 0.0621(5) Uani 1 1 d . . . F3 F 0.6284(2) 0.47560(14) 0.47062(14) 0.0787(7) Uani 1 1 d . . . F4 F 0.4910(2) 0.39662(14) 0.30391(15) 0.0839(7) Uani 1 1 d . . . F5 F 0.41315(17) 0.50996(13) 0.22778(11) 0.0590(5) Uani 1 1 d . . . N1 N -0.24250(19) 1.09479(14) 0.36326(13) 0.0282(4) Uani 1 1 d D . . H1 H -0.213(2) 1.0820(18) 0.3142(11) 0.034 Uiso 1 1 d D . . N2 N -0.18555(17) 0.84494(13) 0.18382(12) 0.0213(4) Uani 1 1 d . . . N3 N -0.10817(17) 0.74275(13) 0.25013(12) 0.0221(4) Uani 1 1 d . . . N4 N 0.01194(17) 0.84619(13) 0.15042(12) 0.0229(4) Uani 1 1 d . . . N5 N 0.07125(17) 0.71816(13) 0.18858(12) 0.0224(4) Uani 1 1 d . . . N6 N 0.40047(19) 0.78536(15) 0.35513(13) 0.0294(5) Uani 1 1 d D . . H6 H 0.386(2) 0.8008(18) 0.4078(9) 0.035 Uiso 1 1 d D . . O1 O -0.35084(17) 1.20320(12) 0.46825(12) 0.0368(4) Uani 1 1 d . . . O2 O -0.12232(16) 0.83462(12) 0.49911(10) 0.0320(4) Uani 1 1 d . . . O3 O -0.08362(15) 0.99030(11) 0.21077(10) 0.0261(4) Uani 1 1 d . . . O4 O 0.07552(15) 0.72350(11) 0.32852(11) 0.0280(4) Uani 1 1 d . . . O5 O -0.35024(16) 0.68614(12) 0.07252(11) 0.0325(4) Uani 1 1 d . . . O6 O -0.21880(17) 0.58682(12) 0.09720(14) 0.0466(5) Uani 1 1 d D . . O7 O 0.0799(2) 0.6408(2) 0.00448(14) 0.0772(8) Uani 1 1 d . . . O8 O -0.11675(17) 0.67999(12) -0.01779(11) 0.0355(4) Uani 1 1 d . . . O9 O 0.27912(17) 1.05324(12) 0.22879(12) 0.0363(4) Uani 1 1 d . . . O10 O 0.49949(16) 0.69207(14) 0.23633(12) 0.0389(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0480(17) 0.0329(16) 0.0479(16) 0.0215(13) 0.0109(13) 0.0071(13) C2 0.0265(13) 0.0249(13) 0.0329(13) 0.0091(11) 0.0017(10) 0.0007(10) C3 0.0229(12) 0.0268(13) 0.0280(12) 0.0130(11) 0.0065(9) 0.0051(10) C4 0.0270(13) 0.0262(13) 0.0257(12) 0.0055(11) 0.0074(10) 0.0033(10) C5 0.0284(13) 0.0353(15) 0.0197(11) 0.0086(11) 0.0031(9) 0.0026(10) C6 0.0215(12) 0.0337(14) 0.0262(12) 0.0156(11) 0.0061(9) 0.0037(10) C7 0.0190(11) 0.0266(13) 0.0258(12) 0.0126(10) 0.0065(9) 0.0014(9) C8 0.0188(11) 0.0273(13) 0.0249(11) 0.0121(10) 0.0061(9) 0.0027(9) C9 0.0446(16) 0.0493(17) 0.0247(13) 0.0213(12) 0.0055(11) 0.0095(13) C10 0.0222(11) 0.0229(12) 0.0239(11) 0.0112(10) 0.0034(9) 0.0031(9) C11 0.0230(12) 0.0271(13) 0.0235(11) 0.0130(10) 0.0040(9) 0.0015(10) C12 0.0273(12) 0.0278(14) 0.0159(11) 0.0116(10) -0.0009(9) -0.0004(10) C13 0.0239(12) 0.0134(11) 0.0239(11) 0.0067(9) 0.0012(9) -0.0024(9) C14 0.0202(11) 0.0213(12) 0.0194(11) 0.0096(9) 0.0019(9) -0.0007(9) C15 0.0266(12) 0.0236(13) 0.0224(11) 0.0107(10) 0.0044(9) -0.0001(10) C17 0.031(4) 0.054(5) 0.056(4) 0.025(4) -0.003(4) -0.013(4) C16 0.027(4) 0.007(3) 0.037(4) -0.002(3) -0.007(3) 0.007(3) C16' 0.047(6) 0.026(4) 0.067(7) 0.007(5) -0.015(5) -0.003(4) C17' 0.035(5) 0.060(5) 0.069(5) 0.017(4) 0.009(4) -0.021(4) C18 0.0231(12) 0.0215(12) 0.0211(11) 0.0079(10) 0.0021(9) -0.0001(9) C19 0.0278(13) 0.0313(14) 0.0268(13) 0.0060(11) 0.0043(10) -0.0041(11) C20 0.0578(18) 0.0409(17) 0.0185(12) 0.0115(12) 0.0024(12) 0.0040(13) C21 0.078(2) 0.0385(18) 0.0282(14) 0.0104(13) -0.0030(14) -0.0096(15) C22 0.0274(13) 0.0284(13) 0.0268(12) 0.0146(11) 0.0047(10) -0.0012(10) C23 0.0219(12) 0.0224(13) 0.0287(12) 0.0092(10) 0.0043(9) 0.0013(9) C24 0.0252(12) 0.0250(13) 0.0216(11) 0.0076(10) 0.0066(9) -0.0026(10) C25 0.0206(11) 0.0245(13) 0.0223(11) 0.0058(10) 0.0079(9) -0.0019(9) C26 0.0220(12) 0.0330(14) 0.0276(12) 0.0130(11) 0.0084(10) 0.0031(10) C27 0.0237(13) 0.0402(16) 0.0262(12) 0.0096(12) 0.0032(10) -0.0039(11) C28 0.0308(14) 0.0271(14) 0.0308(13) 0.0053(11) 0.0074(11) -0.0086(10) C29 0.0302(13) 0.0269(13) 0.0272(12) 0.0100(11) 0.0117(10) -0.0007(10) C30 0.0545(19) 0.0357(17) 0.064(2) 0.0247(15) 0.0062(16) -0.0159(14) C31 0.0207(12) 0.0406(16) 0.0307(13) 0.0145(12) 0.0005(10) 0.0018(11) C32 0.0217(12) 0.0413(16) 0.0330(13) 0.0165(12) 0.0049(10) 0.0065(11) C33 0.0269(13) 0.0395(16) 0.0341(14) 0.0132(13) 0.0072(11) 0.0087(11) C34 0.0421(16) 0.058(2) 0.0349(15) 0.0204(15) 0.0023(12) 0.0192(14) C35 0.064(2) 0.048(2) 0.0543(19) 0.0280(17) 0.0105(16) 0.0252(16) C36 0.068(2) 0.0352(18) 0.0514(19) 0.0138(15) 0.0039(16) 0.0091(15) C37 0.0413(16) 0.0408(17) 0.0359(15) 0.0124(13) -0.0003(12) 0.0042(13) C38 0.0429(16) 0.0538(18) 0.0393(15) 0.0291(14) 0.0119(12) 0.0116(13) C39 0.064(2) 0.0483(19) 0.0516(18) 0.0343(16) 0.0098(15) -0.0006(15) C40 0.068(2) 0.066(2) 0.067(2) 0.0503(19) 0.0115(17) 0.0112(18) Cl1 0.0593(5) 0.0584(5) 0.0777(6) 0.0384(5) 0.0007(4) 0.0000(4) Cl2 0.0431(5) 0.1167(8) 0.0568(5) 0.0372(5) 0.0204(4) 0.0123(5) Cl3 0.1143(8) 0.0776(7) 0.0367(4) 0.0191(4) 0.0154(5) -0.0172(6) Cl4 0.0948(7) 0.0696(6) 0.0428(4) 0.0307(4) 0.0052(4) 0.0031(5) Cl5 0.0637(6) 0.0939(7) 0.0770(6) 0.0510(6) 0.0035(5) 0.0062(5) Cl6 0.0754(6) 0.0556(5) 0.0576(5) 0.0247(4) 0.0198(4) -0.0008(4) Cl7 0.0699(7) 0.1221(11) 0.0990(9) 0.0370(8) -0.0070(6) 0.0048(7) Cl8 0.0648(6) 0.1289(9) 0.0781(6) 0.0698(7) 0.0187(5) 0.0278(6) Cl9 0.1356(10) 0.0738(7) 0.0821(7) 0.0436(6) 0.0494(7) 0.0418(7) F1 0.0352(8) 0.0435(10) 0.0380(8) 0.0140(8) -0.0040(7) -0.0005(7) F2 0.0696(12) 0.0738(13) 0.0398(9) 0.0259(9) -0.0053(9) 0.0241(10) F3 0.1131(17) 0.0661(13) 0.0728(13) 0.0459(11) 0.0087(12) 0.0384(12) F4 0.1283(19) 0.0370(12) 0.0769(14) 0.0210(11) 0.0011(13) 0.0084(11) F5 0.0641(12) 0.0510(11) 0.0460(10) 0.0132(9) -0.0110(9) -0.0069(9) N1 0.0319(11) 0.0253(11) 0.0284(11) 0.0121(9) 0.0085(9) 0.0041(9) N2 0.0217(10) 0.0196(10) 0.0216(9) 0.0086(8) 0.0030(7) -0.0001(8) N3 0.0217(10) 0.0236(10) 0.0210(9) 0.0102(8) 0.0030(8) 0.0015(8) N4 0.0230(10) 0.0221(10) 0.0236(10) 0.0106(8) 0.0028(8) -0.0011(8) N5 0.0201(10) 0.0217(10) 0.0246(10) 0.0104(8) 0.0012(8) -0.0004(8) N6 0.0240(11) 0.0389(13) 0.0262(10) 0.0153(10) 0.0051(9) 0.0038(9) O1 0.0399(10) 0.0344(10) 0.0382(10) 0.0160(8) 0.0145(8) 0.0116(8) O2 0.0400(10) 0.0360(10) 0.0237(8) 0.0167(8) 0.0049(7) 0.0082(8) O3 0.0336(9) 0.0202(9) 0.0262(8) 0.0126(7) 0.0022(7) -0.0003(7) O4 0.0270(9) 0.0295(9) 0.0312(9) 0.0182(8) -0.0008(7) 0.0017(7) O5 0.0307(9) 0.0306(10) 0.0317(9) 0.0132(8) -0.0074(7) -0.0021(7) O6 0.0413(11) 0.0225(10) 0.0632(13) 0.0165(9) -0.0235(10) -0.0084(8) O7 0.0412(13) 0.109(2) 0.0328(11) -0.0100(12) 0.0016(10) 0.0257(13) O8 0.0477(11) 0.0358(11) 0.0203(8) 0.0108(8) 0.0028(8) 0.0082(8) O9 0.0417(10) 0.0283(10) 0.0410(10) 0.0176(8) 0.0071(8) -0.0073(8) O10 0.0310(10) 0.0556(12) 0.0325(10) 0.0210(9) 0.0091(8) 0.0106(9) _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 C2 1.508(4) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 O1 1.220(3) . ? C2 N1 1.355(3) . ? C3 C4 1.390(3) . ? C3 C8 1.400(3) . ? C3 N1 1.430(3) . ? C4 C5 1.380(3) . ? C4 H4 0.9500 . ? C5 C6 1.395(3) . ? C5 H5 0.9500 . ? C6 O2 1.362(3) . ? C6 C7 1.398(3) . ? C7 C8 1.402(3) . ? C7 C11 1.517(3) . ? C8 C10 1.511(3) . ? C9 O2 1.426(3) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 N2 1.476(3) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 N3 1.455(3) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 O3 1.222(3) . ? C12 N4 1.366(3) . ? C12 N2 1.390(3) . ? C13 O4 1.219(3) . ? C13 N3 1.363(3) . ? C13 N5 1.385(3) . ? C14 N2 1.444(3) . ? C14 N3 1.446(3) . ? C14 C15 1.545(3) . ? C14 C18 1.570(3) . ? C15 O5 1.193(3) . ? C15 O6 1.316(3) . ? C17 C16 1.509(8) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C16 O6 1.476(7) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C16' C17' 1.474(8) . ? C16' O6 1.488(8) . ? C16' H16C 0.9900 . ? C16' H16D 0.9900 . ? C17' H17D 0.9800 . ? C17' H17E 0.9800 . ? C17' H17F 0.9800 . ? C18 N5 1.451(3) . ? C18 N4 1.452(3) . ? C18 C19 1.536(3) . ? C19 O7 1.180(3) . ? C19 O8 1.307(3) . ? C20 O8 1.477(3) . ? C20 C21 1.490(4) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 N4 1.462(3) . ? C22 C24 1.522(3) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 N5 1.455(3) . ? C23 C25 1.519(3) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 C25 1.397(3) . ? C24 C29 1.411(3) . ? C25 C26 1.404(3) . ? C26 C27 1.378(3) . ? C26 N6 1.434(3) . ? C27 C28 1.387(4) . ? C27 H27 0.9500 . ? C28 C29 1.379(3) . ? C28 H28 0.9500 . ? C29 O9 1.363(3) . ? C30 O9 1.422(3) . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 0.9800 . ? C31 O10 1.219(3) . ? C31 N6 1.340(3) . ? C31 C32 1.508(3) . ? C32 C33 1.378(3) . ? C32 C37 1.388(4) . ? C33 F1 1.344(3) . ? C33 C34 1.382(4) . ? C34 F2 1.345(3) . ? C34 C35 1.366(4) . ? C35 F3 1.339(3) . ? C35 C36 1.361(4) . ? C36 F4 1.349(4) . ? C36 C37 1.371(4) . ? C37 F5 1.350(3) . ? C38 Cl2 1.739(3) . ? C38 Cl1 1.745(3) . ? C38 Cl3 1.751(3) . ? C38 H38 1.0000 . ? C39 Cl6 1.754(3) . ? C39 Cl4 1.756(3) . ? C39 Cl5 1.757(3) . ? C39 H39 1.0000 . ? C40 Cl7 1.737(4) . ? C40 Cl9 1.740(3) . ? C40 Cl8 1.755(3) . ? C40 H40 1.0000 . ? N1 H1 0.855(10) . ? N6 H6 0.843(10) . ? 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 C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O1 C2 N1 123.5(2) . . ? O1 C2 C1 122.1(2) . . ? N1 C2 C1 114.4(2) . . ? C4 C3 C8 120.1(2) . . ? C4 C3 N1 120.3(2) . . ? C8 C3 N1 119.5(2) . . ? C5 C4 C3 120.6(2) . . ? C5 C4 H4 119.7 . . ? C3 C4 H4 119.7 . . ? C4 C5 C6 120.0(2) . . ? C4 C5 H5 120.0 . . ? C6 C5 H5 120.0 . . ? O2 C6 C5 124.2(2) . . ? O2 C6 C7 116.1(2) . . ? C5 C6 C7 119.7(2) . . ? C6 C7 C8 120.2(2) . . ? C6 C7 C11 119.45(19) . . ? C8 C7 C11 120.31(19) . . ? C3 C8 C7 119.1(2) . . ? C3 C8 C10 121.7(2) . . ? C7 C8 C10 119.3(2) . . ? O2 C9 H9A 109.5 . . ? O2 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? O2 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N2 C10 C8 114.44(17) . . ? N2 C10 H10A 108.7 . . ? C8 C10 H10A 108.7 . . ? N2 C10 H10B 108.7 . . ? C8 C10 H10B 108.7 . . ? H10A C10 H10B 107.6 . . ? N3 C11 C7 111.22(18) . . ? N3 C11 H11A 109.4 . . ? C7 C11 H11A 109.4 . . ? N3 C11 H11B 109.4 . . ? C7 C11 H11B 109.4 . . ? H11A C11 H11B 108.0 . . ? O3 C12 N4 126.8(2) . . ? O3 C12 N2 125.2(2) . . ? N4 C12 N2 108.01(19) . . ? O4 C13 N3 126.7(2) . . ? O4 C13 N5 125.0(2) . . ? N3 C13 N5 108.33(18) . . ? N2 C14 N3 113.68(17) . . ? N2 C14 C15 110.70(17) . . ? N3 C14 C15 110.43(17) . . ? N2 C14 C18 103.43(16) . . ? N3 C14 C18 101.94(16) . . ? C15 C14 C18 116.36(17) . . ? O5 C15 O6 125.7(2) . . ? O5 C15 C14 124.0(2) . . ? O6 C15 C14 110.22(19) . . ? O6 C16 C17 105.2(5) . . ? O6 C16 H16A 110.7 . . ? C17 C16 H16A 110.7 . . ? O6 C16 H16B 110.7 . . ? C17 C16 H16B 110.7 . . ? H16A C16 H16B 108.8 . . ? C17' C16' O6 109.1(6) . . ? C17' C16' H16C 109.9 . . ? O6 C16' H16C 109.9 . . ? C17' C16' H16D 109.9 . . ? O6 C16' H16D 109.9 . . ? H16C C16' H16D 108.3 . . ? C16' C17' H17D 109.5 . . ? C16' C17' H17E 109.5 . . ? H17D C17' H17E 109.5 . . ? C16' C17' H17F 109.5 . . ? H17D C17' H17F 109.5 . . ? H17E C17' H17F 109.5 . . ? N5 C18 N4 113.20(18) . . ? N5 C18 C19 110.84(18) . . ? N4 C18 C19 108.88(18) . . ? N5 C18 C14 103.65(17) . . ? N4 C18 C14 102.21(16) . . ? C19 C18 C14 117.88(18) . . ? O7 C19 O8 125.2(2) . . ? O7 C19 C18 123.3(2) . . ? O8 C19 C18 111.4(2) . . ? O8 C20 C21 111.1(2) . . ? O8 C20 H20A 109.4 . . ? C21 C20 H20A 109.4 . . ? O8 C20 H20B 109.4 . . ? C21 C20 H20B 109.4 . . ? H20A C20 H20B 108.0 . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? N4 C22 C24 113.92(18) . . ? N4 C22 H22A 108.8 . . ? C24 C22 H22A 108.8 . . ? N4 C22 H22B 108.8 . . ? C24 C22 H22B 108.8 . . ? H22A C22 H22B 107.7 . . ? N5 C23 C25 115.67(18) . . ? N5 C23 H23A 108.4 . . ? C25 C23 H23A 108.4 . . ? N5 C23 H23B 108.4 . . ? C25 C23 H23B 108.4 . . ? H23A C23 H23B 107.4 . . ? C25 C24 C29 119.3(2) . . ? C25 C24 C22 122.1(2) . . ? C29 C24 C22 118.5(2) . . ? C24 C25 C26 119.3(2) . . ? C24 C25 C23 120.8(2) . . ? C26 C25 C23 119.7(2) . . ? C27 C26 C25 120.3(2) . . ? C27 C26 N6 118.4(2) . . ? C25 C26 N6 121.3(2) . . ? C26 C27 C28 120.8(2) . . ? C26 C27 H27 119.6 . . ? C28 C27 H27 119.6 . . ? C29 C28 C27 119.7(2) . . ? C29 C28 H28 120.1 . . ? C27 C28 H28 120.1 . . ? O9 C29 C28 124.1(2) . . ? O9 C29 C24 115.4(2) . . ? C28 C29 C24 120.5(2) . . ? O9 C30 H30A 109.5 . . ? O9 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? O9 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? O10 C31 N6 124.7(2) . . ? O10 C31 C32 120.1(2) . . ? N6 C31 C32 115.1(2) . . ? C33 C32 C37 116.3(2) . . ? C33 C32 C31 123.2(2) . . ? C37 C32 C31 120.3(2) . . ? F1 C33 C32 119.9(2) . . ? F1 C33 C34 118.1(2) . . ? C32 C33 C34 122.1(3) . . ? F2 C34 C35 120.4(3) . . ? F2 C34 C33 120.2(3) . . ? C35 C34 C33 119.4(3) . . ? F3 C35 C36 120.1(3) . . ? F3 C35 C34 119.5(3) . . ? C36 C35 C34 120.4(3) . . ? F4 C36 C35 119.8(3) . . ? F4 C36 C37 120.7(3) . . ? C35 C36 C37 119.5(3) . . ? F5 C37 C36 118.0(3) . . ? F5 C37 C32 119.7(2) . . ? C36 C37 C32 122.3(3) . . ? Cl2 C38 Cl1 110.86(16) . . ? Cl2 C38 Cl3 110.91(16) . . ? Cl1 C38 Cl3 111.06(14) . . ? Cl2 C38 H38 108.0 . . ? Cl1 C38 H38 108.0 . . ? Cl3 C38 H38 108.0 . . ? Cl6 C39 Cl4 110.33(17) . . ? Cl6 C39 Cl5 110.32(16) . . ? Cl4 C39 Cl5 110.27(18) . . ? Cl6 C39 H39 108.6 . . ? Cl4 C39 H39 108.6 . . ? Cl5 C39 H39 108.6 . . ? Cl7 C40 Cl9 110.37(19) . . ? Cl7 C40 Cl8 110.4(2) . . ? Cl9 C40 Cl8 111.39(17) . . ? Cl7 C40 H40 108.2 . . ? Cl9 C40 H40 108.2 . . ? Cl8 C40 H40 108.2 . . ? C2 N1 C3 125.9(2) . . ? C2 N1 H1 116.7(17) . . ? C3 N1 H1 117.4(17) . . ? C12 N2 C14 111.07(17) . . ? C12 N2 C10 118.92(18) . . ? C14 N2 C10 120.03(17) . . ? C13 N3 C14 113.43(17) . . ? C13 N3 C11 123.51(18) . . ? C14 N3 C11 122.70(17) . . ? C12 N4 C18 113.03(18) . . ? C12 N4 C22 124.78(19) . . ? C18 N4 C22 121.81(18) . . ? C13 N5 C18 110.65(17) . . ? C13 N5 C23 118.42(18) . . ? C18 N5 C23 123.41(18) . . ? C31 N6 C26 120.5(2) . . ? C31 N6 H6 123.4(18) . . ? C26 N6 H6 115.2(18) . . ? C6 O2 C9 117.34(19) . . ? C15 O6 C16 120.9(4) . . ? C15 O6 C16' 110.3(4) . . ? C16 O6 C16' 20.0(6) . . ? C19 O8 C20 115.57(19) . . ? C29 O9 C30 117.4(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C8 C3 C4 C5 0.3(3) . . . . ? N1 C3 C4 C5 -176.0(2) . . . . ? C3 C4 C5 C6 3.3(3) . . . . ? C4 C5 C6 O2 175.4(2) . . . . ? C4 C5 C6 C7 -3.0(3) . . . . ? O2 C6 C7 C8 -179.48(19) . . . . ? C5 C6 C7 C8 -1.0(3) . . . . ? O2 C6 C7 C11 -1.2(3) . . . . ? C5 C6 C7 C11 177.3(2) . . . . ? C4 C3 C8 C7 -4.2(3) . . . . ? N1 C3 C8 C7 172.11(19) . . . . ? C4 C3 C8 C10 176.1(2) . . . . ? N1 C3 C8 C10 -7.6(3) . . . . ? C6 C7 C8 C3 4.5(3) . . . . ? C11 C7 C8 C3 -173.7(2) . . . . ? C6 C7 C8 C10 -175.7(2) . . . . ? C11 C7 C8 C10 6.0(3) . . . . ? C3 C8 C10 N2 112.1(2) . . . . ? C7 C8 C10 N2 -67.6(3) . . . . ? C6 C7 C11 N3 -119.6(2) . . . . ? C8 C7 C11 N3 58.6(3) . . . . ? N2 C14 C15 O5 2.4(3) . . . . ? N3 C14 C15 O5 129.2(2) . . . . ? C18 C14 C15 O5 -115.3(2) . . . . ? N2 C14 C15 O6 -175.44(19) . . . . ? N3 C14 C15 O6 -48.6(2) . . . . ? C18 C14 C15 O6 66.9(2) . . . . ? N2 C14 C18 N5 129.06(17) . . . . ? N3 C14 C18 N5 10.9(2) . . . . ? C15 C14 C18 N5 -109.3(2) . . . . ? N2 C14 C18 N4 11.2(2) . . . . ? N3 C14 C18 N4 -106.99(18) . . . . ? C15 C14 C18 N4 132.80(18) . . . . ? N2 C14 C18 C19 -108.1(2) . . . . ? N3 C14 C18 C19 133.7(2) . . . . ? C15 C14 C18 C19 13.5(3) . . . . ? N5 C18 C19 O7 -28.6(4) . . . . ? N4 C18 C19 O7 96.5(3) . . . . ? C14 C18 C19 O7 -147.8(3) . . . . ? N5 C18 C19 O8 155.8(2) . . . . ? N4 C18 C19 O8 -79.1(2) . . . . ? C14 C18 C19 O8 36.6(3) . . . . ? N4 C22 C24 C25 55.3(3) . . . . ? N4 C22 C24 C29 -128.7(2) . . . . ? C29 C24 C25 C26 4.1(3) . . . . ? C22 C24 C25 C26 -179.9(2) . . . . ? C29 C24 C25 C23 -171.03(19) . . . . ? C22 C24 C25 C23 5.0(3) . . . . ? N5 C23 C25 C24 -60.3(3) . . . . ? N5 C23 C25 C26 124.6(2) . . . . ? C24 C25 C26 C27 -2.6(3) . . . . ? C23 C25 C26 C27 172.5(2) . . . . ? C24 C25 C26 N6 178.07(19) . . . . ? C23 C25 C26 N6 -6.8(3) . . . . ? C25 C26 C27 C28 -0.4(3) . . . . ? N6 C26 C27 C28 178.9(2) . . . . ? C26 C27 C28 C29 2.0(4) . . . . ? C27 C28 C29 O9 -179.5(2) . . . . ? C27 C28 C29 C24 -0.5(3) . . . . ? C25 C24 C29 O9 176.52(19) . . . . ? C22 C24 C29 O9 0.3(3) . . . . ? C25 C24 C29 C28 -2.5(3) . . . . ? C22 C24 C29 C28 -178.7(2) . . . . ? O10 C31 C32 C33 123.5(3) . . . . ? N6 C31 C32 C33 -56.7(3) . . . . ? O10 C31 C32 C37 -51.8(3) . . . . ? N6 C31 C32 C37 128.0(3) . . . . ? C37 C32 C33 F1 178.6(2) . . . . ? C31 C32 C33 F1 3.1(4) . . . . ? C37 C32 C33 C34 -0.5(4) . . . . ? C31 C32 C33 C34 -176.0(2) . . . . ? F1 C33 C34 F2 1.2(4) . . . . ? C32 C33 C34 F2 -179.8(2) . . . . ? F1 C33 C34 C35 -179.5(2) . . . . ? C32 C33 C34 C35 -0.4(4) . . . . ? F2 C34 C35 F3 -0.3(5) . . . . ? C33 C34 C35 F3 -179.7(3) . . . . ? F2 C34 C35 C36 179.7(3) . . . . ? C33 C34 C35 C36 0.4(5) . . . . ? F3 C35 C36 F4 1.1(5) . . . . ? C34 C35 C36 F4 -178.9(3) . . . . ? F3 C35 C36 C37 -179.4(3) . . . . ? C34 C35 C36 C37 0.5(5) . . . . ? F4 C36 C37 F5 0.4(5) . . . . ? C35 C36 C37 F5 -179.1(3) . . . . ? F4 C36 C37 C32 178.0(3) . . . . ? C35 C36 C37 C32 -1.5(5) . . . . ? C33 C32 C37 F5 179.0(2) . . . . ? C31 C32 C37 F5 -5.4(4) . . . . ? C33 C32 C37 C36 1.4(4) . . . . ? C31 C32 C37 C36 177.0(3) . . . . ? O1 C2 N1 C3 -8.3(4) . . . . ? C1 C2 N1 C3 173.0(2) . . . . ? C4 C3 N1 C2 -39.7(3) . . . . ? C8 C3 N1 C2 144.0(2) . . . . ? O3 C12 N2 C14 -167.36(19) . . . . ? N4 C12 N2 C14 13.8(2) . . . . ? O3 C12 N2 C10 -21.7(3) . . . . ? N4 C12 N2 C10 159.41(17) . . . . ? N3 C14 N2 C12 94.2(2) . . . . ? C15 C14 N2 C12 -140.84(17) . . . . ? C18 C14 N2 C12 -15.5(2) . . . . ? N3 C14 N2 C10 -51.0(3) . . . . ? C15 C14 N2 C10 73.9(2) . . . . ? C18 C14 N2 C10 -160.72(17) . . . . ? C8 C10 N2 C12 -66.9(2) . . . . ? C8 C10 N2 C14 75.6(2) . . . . ? O4 C13 N3 C14 176.4(2) . . . . ? N5 C13 N3 C14 -4.8(2) . . . . ? O4 C13 N3 C11 3.2(3) . . . . ? N5 C13 N3 C11 -177.92(18) . . . . ? N2 C14 N3 C13 -114.8(2) . . . . ? C15 C14 N3 C13 120.1(2) . . . . ? C18 C14 N3 C13 -4.2(2) . . . . ? N2 C14 N3 C11 58.5(3) . . . . ? C15 C14 N3 C11 -66.6(2) . . . . ? C18 C14 N3 C11 169.08(18) . . . . ? C7 C11 N3 C13 90.8(2) . . . . ? C7 C11 N3 C14 -81.8(2) . . . . ? O3 C12 N4 C18 175.5(2) . . . . ? N2 C12 N4 C18 -5.6(2) . . . . ? O3 C12 N4 C22 2.6(3) . . . . ? N2 C12 N4 C22 -178.58(18) . . . . ? N5 C18 N4 C12 -114.6(2) . . . . ? C19 C18 N4 C12 121.62(19) . . . . ? C14 C18 N4 C12 -3.8(2) . . . . ? N5 C18 N4 C22 58.6(3) . . . . ? C19 C18 N4 C22 -65.2(2) . . . . ? C14 C18 N4 C22 169.40(18) . . . . ? C24 C22 N4 C12 94.4(2) . . . . ? C24 C22 N4 C18 -78.0(3) . . . . ? O4 C13 N5 C18 -168.5(2) . . . . ? N3 C13 N5 C18 12.6(2) . . . . ? O4 C13 N5 C23 -17.7(3) . . . . ? N3 C13 N5 C23 163.39(18) . . . . ? N4 C18 N5 C13 95.3(2) . . . . ? C19 C18 N5 C13 -141.99(19) . . . . ? C14 C18 N5 C13 -14.6(2) . . . . ? N4 C18 N5 C23 -53.7(3) . . . . ? C19 C18 N5 C23 68.9(3) . . . . ? C14 C18 N5 C23 -163.67(18) . . . . ? C25 C23 N5 C13 -74.7(2) . . . . ? C25 C23 N5 C18 72.2(3) . . . . ? O10 C31 N6 C26 -6.0(4) . . . . ? C32 C31 N6 C26 174.2(2) . . . . ? C27 C26 N6 C31 -104.0(3) . . . . ? C25 C26 N6 C31 75.3(3) . . . . ? C5 C6 O2 C9 7.1(3) . . . . ? C7 C6 O2 C9 -174.5(2) . . . . ? O5 C15 O6 C16 7.0(5) . . . . ? C14 C15 O6 C16 -175.2(4) . . . . ? O5 C15 O6 C16' -11.9(7) . . . . ? C14 C15 O6 C16' 165.9(7) . . . . ? C17 C16 O6 C15 -97.4(9) . . . . ? C17 C16 O6 C16' -35.0(16) . . . . ? C17' C16' O6 C15 -142.0(10) . . . . ? C17' C16' O6 C16 92.2(19) . . . . ? O7 C19 O8 C20 3.8(4) . . . . ? C18 C19 O8 C20 179.3(2) . . . . ? C21 C20 O8 C19 71.4(3) . . . . ? C28 C29 O9 C30 16.5(3) . . . . ? C24 C29 O9 C30 -162.5(2) . . . . ? 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 C23 H23A O7 0.99 2.35 3.004(3) 122.7 . C40 H40 O4 1.00 2.06 3.027(4) 161.7 1_655 C38 H38 O5 1.00 2.19 3.075(3) 146.1 1_655 C30 H30A F2 0.98 2.54 3.393(4) 145.9 2_676 C17' H17D O7 0.98 2.48 3.295(12) 140.2 2_565 C11 H11B O10 0.99 2.34 3.314(3) 168.8 1_455 C4 H4 O4 0.95 2.52 3.380(3) 151.1 2_576 N6 H6 O1 0.843(10) 2.188(12) 3.006(3) 164(2) 2_576 N1 H1 O3 0.855(10) 2.315(16) 3.071(2) 148(2) . _diffrn_measured_fraction_theta_max 0.970 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.970 _refine_diff_density_max 0.577 _refine_diff_density_min -0.675 _refine_diff_density_rms 0.087 #===END data_f:\cf3-4ucc\work\050807dm _database_code_depnum_ccdc_archive 'CCDC 782748' #TrackingRef '- CIFs Combined CC.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C44 H44 F6 N10 O16, C2 H4 Cl2' _chemical_formula_sum 'C46 H48 Cl2 F6 N10 O16' _chemical_formula_weight 1181.84 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 31.260(11) _cell_length_b 13.333(5) _cell_length_c 27.209(10) _cell_angle_alpha 90.00 _cell_angle_beta 112.158(6) _cell_angle_gamma 90.00 _cell_volume 10504(6) _cell_formula_units_Z 8 _cell_measurement_temperature 292(2) _cell_measurement_reflns_used 6362 _cell_measurement_theta_min 2.42 _cell_measurement_theta_max 20.82 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.495 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 4880 _exptl_absorpt_coefficient_mu 0.224 _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 292(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 36605 _diffrn_reflns_av_R_equivalents 0.0878 _diffrn_reflns_av_sigmaI/netI 0.0820 _diffrn_reflns_limit_h_min -37 _diffrn_reflns_limit_h_max 35 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 1.41 _diffrn_reflns_theta_max 25.00 _reflns_number_total 9236 _reflns_number_gt 5034 _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 '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^)+(0.1281P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 9236 _refine_ls_number_parameters 834 _refine_ls_number_restraints 95 _refine_ls_R_factor_all 0.1271 _refine_ls_R_factor_gt 0.0705 _refine_ls_wR_factor_ref 0.2233 _refine_ls_wR_factor_gt 0.1929 _refine_ls_goodness_of_fit_ref 0.986 _refine_ls_restrained_S_all 0.998 _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 C1 C -0.02793(12) 0.4279(2) 0.36552(14) 0.0513(8) Uani 1 1 d . . . C2 C -0.04224(11) 0.2987(2) 0.41588(13) 0.0503(8) Uani 1 1 d . . . C3 C -0.04492(13) 0.1479(3) 0.36908(15) 0.0576(9) Uani 1 1 d . . . C4 C -0.08171(11) 0.3025(2) 0.35932(13) 0.0528(8) Uani 1 1 d . . . C5 C -0.05897(13) 0.3031(3) 0.46287(15) 0.0594(9) Uani 1 1 d . . . C6 C -0.10433(19) 0.2172(4) 0.5027(2) 0.1073(17) Uani 1 1 d . . . H6A H -0.0787 0.1942 0.5338 0.129 Uiso 1 1 calc R . . H6B H -0.1151 0.2807 0.5111 0.129 Uiso 1 1 calc R . . C7 C -0.1409(2) 0.1453(5) 0.4883(3) 0.150(3) Uani 1 1 d . . . H7A H -0.1677 0.1723 0.4606 0.225 Uiso 1 1 calc R . . H7B H -0.1483 0.1301 0.5187 0.225 Uiso 1 1 calc R . . H7C H -0.1313 0.0851 0.4759 0.225 Uiso 1 1 calc R . . C8 C -0.13011(14) 0.3292(3) 0.35773(15) 0.0638(10) Uani 1 1 d . . . C9 C -0.17036(16) 0.4571(4) 0.3841(2) 0.0921(14) Uani 1 1 d . . . H9A H -0.1948 0.4473 0.3496 0.110 Uiso 1 1 calc R . . H9B H -0.1660 0.5287 0.3902 0.110 Uiso 1 1 calc R . . C10 C -0.18462(18) 0.4129(5) 0.4250(2) 0.1132(18) Uani 1 1 d . . . H10A H -0.1949 0.3453 0.4153 0.170 Uiso 1 1 calc R . . H10B H -0.2094 0.4517 0.4280 0.170 Uiso 1 1 calc R . . H10C H -0.1589 0.4128 0.4584 0.170 Uiso 1 1 calc R . . C11 C -0.10342(13) 0.1835(3) 0.28132(14) 0.0609(9) Uani 1 1 d . . . H11A H -0.1353 0.2050 0.2702 0.073 Uiso 1 1 calc R . . H11B H -0.1036 0.1114 0.2767 0.073 Uiso 1 1 calc R . . C12 C -0.08995(13) 0.4054(3) 0.27740(14) 0.0603(9) Uani 1 1 d . . . H12A H -0.0816 0.4730 0.2713 0.072 Uiso 1 1 calc R . . H12B H -0.1230 0.4044 0.2689 0.072 Uiso 1 1 calc R . . C13 C -0.07907(11) 0.3348(3) 0.24018(13) 0.0529(8) Uani 1 1 d . . . C14 C -0.08319(12) 0.2306(3) 0.24425(14) 0.0561(9) Uani 1 1 d . . . C15 C -0.07025(12) 0.1668(3) 0.21110(14) 0.0617(9) Uani 1 1 d . . . C16 C -0.05584(14) 0.2056(3) 0.17297(15) 0.0681(10) Uani 1 1 d . . . H16 H -0.0472 0.1631 0.1512 0.082 Uiso 1 1 calc R . . C17 C -0.05448(13) 0.3071(3) 0.16755(15) 0.0688(10) Uani 1 1 d . . . H17 H -0.0462 0.3332 0.1407 0.083 Uiso 1 1 calc R . . C18 C -0.06504(12) 0.3723(3) 0.20060(14) 0.0581(9) Uani 1 1 d . B . C19 C -0.09284(15) 0.5467(3) 0.18363(15) 0.0669(10) Uani 1 1 d . B . C20 C -0.0576(2) -0.0020(3) 0.1894(2) 0.1006(16) Uani 1 1 d . . . H20A H -0.0764 0.0056 0.1524 0.151 Uiso 1 1 calc R . . H20B H -0.0604 -0.0693 0.2004 0.151 Uiso 1 1 calc R . . H20C H -0.0259 0.0116 0.1951 0.151 Uiso 1 1 calc R . . C21 C 0.00737(12) 0.1479(3) 0.46369(14) 0.0590(9) Uani 1 1 d . . . H21A H -0.0047 0.1607 0.4911 0.071 Uiso 1 1 calc R . . H21B H 0.0045 0.0765 0.4563 0.071 Uiso 1 1 calc R . . C22 C 0.02734(11) 0.4180(2) 0.45836(14) 0.0556(9) Uani 1 1 d . . . H22A H 0.0357 0.4833 0.4490 0.067 Uiso 1 1 calc R . . H22B H 0.0197 0.4269 0.4895 0.067 Uiso 1 1 calc R . . C23 C 0.10864(12) 0.3942(3) 0.47487(14) 0.0552(9) Uani 1 1 d . . . C24 C 0.12792(12) 0.2461(3) 0.52310(14) 0.0585(9) Uani 1 1 d . . . C25 C 0.08568(14) 0.1186(3) 0.46798(14) 0.0605(9) Uani 1 1 d . . . C26 C 0.07538(12) 0.2672(2) 0.50877(14) 0.0551(9) Uani 1 1 d . . . C27 C 0.15489(14) 0.2177(3) 0.58181(17) 0.0672(10) Uani 1 1 d . . . C28 C 0.16703(18) 0.0877(4) 0.64353(18) 0.0927(14) Uani 1 1 d . . . H28A H 0.2001 0.0825 0.6529 0.111 Uiso 1 1 calc R . . H28B H 0.1615 0.1330 0.6684 0.111 Uiso 1 1 calc R . . C29 C 0.1482(2) -0.0093(5) 0.6463(3) 0.158(3) Uani 1 1 d . . . H29A H 0.1156 -0.0034 0.6380 0.237 Uiso 1 1 calc R . . H29B H 0.1630 -0.0359 0.6815 0.237 Uiso 1 1 calc R . . H29C H 0.1534 -0.0536 0.6213 0.237 Uiso 1 1 calc R . . C30 C 0.06562(13) 0.2974(3) 0.55811(15) 0.0639(10) Uani 1 1 d . A . C31 C 0.0434(6) 0.2521(11) 0.6295(5) 0.119(6) Uani 0.60 1 d PD A 1 H31A H 0.0739 0.2641 0.6561 0.143 Uiso 0.60 1 calc PR A 1 H31B H 0.0249 0.3120 0.6262 0.143 Uiso 0.60 1 calc PR A 1 C32 C 0.0225(4) 0.1693(6) 0.6444(4) 0.098(3) Uani 0.60 1 d PD A 1 H32A H -0.0060 0.1527 0.6158 0.147 Uiso 0.60 1 calc PR A 1 H32B H 0.0162 0.1866 0.6753 0.147 Uiso 0.60 1 calc PR A 1 H32C H 0.0429 0.1127 0.6522 0.147 Uiso 0.60 1 calc PR A 1 C31' C 0.0291(6) 0.2620(11) 0.6172(6) 0.062(4) Uani 0.40 1 d PDU A 2 H31C H 0.0328 0.3338 0.6227 0.074 Uiso 0.40 1 calc PR A 2 H31D H -0.0031 0.2444 0.6078 0.074 Uiso 0.40 1 calc PR A 2 C32' C 0.0587(8) 0.2069(18) 0.6636(8) 0.157(7) Uani 0.40 1 d PDU A 2 H32D H 0.0687 0.1459 0.6526 0.236 Uiso 0.40 1 calc PR A 2 H32E H 0.0418 0.1914 0.6857 0.236 Uiso 0.40 1 calc PR A 2 H32F H 0.0851 0.2471 0.6832 0.236 Uiso 0.40 1 calc PR A 2 C33 C 0.18954(12) 0.3391(3) 0.50606(15) 0.0646(10) Uani 1 1 d . . . H33A H 0.2110 0.3012 0.5355 0.078 Uiso 1 1 calc R . . H33B H 0.2007 0.4077 0.5094 0.078 Uiso 1 1 calc R . . C34 C 0.16870(14) 0.1275(3) 0.48189(17) 0.0719(11) Uani 1 1 d . . . H34A H 0.1632 0.0599 0.4677 0.086 Uiso 1 1 calc R . . H34B H 0.1935 0.1248 0.5165 0.086 Uiso 1 1 calc R . . C35 C 0.18967(12) 0.2957(3) 0.45488(15) 0.0661(10) Uani 1 1 d . . . C36 C 0.18314(13) 0.1930(3) 0.44562(15) 0.0697(10) Uani 1 1 d . . . C37 C 0.18813(14) 0.1517(4) 0.40023(18) 0.0813(12) Uani 1 1 d . . . C38 C 0.19751(16) 0.2144(5) 0.36487(19) 0.0909(14) Uani 1 1 d . . . H38 H 0.2016 0.1875 0.3354 0.109 Uiso 1 1 calc R . . C39 C 0.20079(15) 0.3156(4) 0.37323(18) 0.0882(13) Uani 1 1 d . . . H39 H 0.2057 0.3571 0.3484 0.106 Uiso 1 1 calc R . . C40 C 0.19695(13) 0.3575(4) 0.41771(16) 0.0730(11) Uani 1 1 d . C . C41 C 0.22705(15) 0.5270(4) 0.41932(18) 0.0869(13) Uani 1 1 d . C . C42 C 0.2224(2) 0.6329(5) 0.4373(3) 0.1030(16) Uani 1 1 d D . . C43 C 0.1859(2) 0.0032(5) 0.3497(2) 0.126(2) Uani 1 1 d . . . H43A H 0.1606 0.0258 0.3188 0.190 Uiso 1 1 calc R . . H43B H 0.1843 -0.0683 0.3527 0.190 Uiso 1 1 calc R . . H43C H 0.2145 0.0209 0.3464 0.190 Uiso 1 1 calc R . . C44 C -0.07894(19) 0.6518(4) 0.1741(2) 0.0883(13) Uani 1 1 d D . . F1 F -0.1080(5) 0.7178(6) 0.1738(9) 0.140(5) Uani 0.54 1 d PD B 1 F2 F -0.0384(4) 0.6756(11) 0.2035(7) 0.155(8) Uani 0.54 1 d PD B 1 F3 F -0.0784(6) 0.6578(7) 0.1254(3) 0.117(3) Uani 0.54 1 d PD B 1 F1' F -0.0393(6) 0.6615(10) 0.1734(13) 0.182(13) Uani 0.46 1 d PD B 2 F2' F -0.1089(7) 0.6963(15) 0.1364(10) 0.217(10) Uani 0.46 1 d PD B 2 F3' F -0.0760(10) 0.7055(11) 0.2165(8) 0.164(5) Uani 0.46 1 d PD B 2 F4 F 0.2324(5) 0.7037(9) 0.4105(5) 0.135(4) Uani 0.63 1 d PD C 1 F5 F 0.2527(3) 0.6406(9) 0.4873(3) 0.129(3) Uani 0.63 1 d PD C 1 F6 F 0.1829(2) 0.6520(10) 0.4391(5) 0.122(4) Uani 0.63 1 d PD C 1 F4' F 0.2610(6) 0.668(2) 0.4710(8) 0.245(18) Uani 0.37 1 d PD C 2 F5' F 0.1901(6) 0.6541(18) 0.4541(9) 0.178(13) Uani 0.37 1 d PD C 2 F6' F 0.2135(9) 0.687(2) 0.3937(7) 0.190(12) Uani 0.37 1 d PD C 2 N1 N -0.01369(9) 0.38300(19) 0.41490(11) 0.0519(7) Uani 1 1 d . . . N2 N -0.06633(10) 0.3811(2) 0.33331(11) 0.0568(7) Uani 1 1 d . . . N3 N -0.02118(10) 0.2011(2) 0.41584(11) 0.0555(7) Uani 1 1 d . . . N4 N -0.08062(10) 0.2050(2) 0.33729(11) 0.0546(7) Uani 1 1 d . . . N5 N 0.06750(9) 0.35276(19) 0.47248(11) 0.0529(7) Uani 1 1 d . . . N6 N 0.14466(10) 0.3386(2) 0.51016(11) 0.0584(7) Uani 1 1 d . . . N7 N 0.12699(10) 0.1650(2) 0.48756(12) 0.0625(8) Uani 1 1 d . . . N8 N 0.05483(10) 0.1735(2) 0.48369(11) 0.0574(7) Uani 1 1 d . . . N9 N 0.19771(11) 0.4628(3) 0.42579(13) 0.0786(9) Uani 1 1 d . . . H9 H 0.1769 0.4870 0.4359 0.094 Uiso 1 1 calc R C . N10 N -0.06003(11) 0.4773(2) 0.19330(12) 0.0645(8) Uani 1 1 d . . . H10 H -0.0333 0.4975 0.1953 0.077 Uiso 1 1 calc R B . O1 O -0.00849(8) 0.49735(17) 0.35336(10) 0.0624(6) Uani 1 1 d . . . O2 O -0.03455(9) 0.06491(19) 0.35960(11) 0.0736(7) Uani 1 1 d . . . O3 O -0.04452(10) 0.3592(2) 0.49901(12) 0.0833(8) Uani 1 1 d . . . O4 O -0.08876(9) 0.2308(2) 0.45799(10) 0.0744(8) Uani 1 1 d . . . O5 O -0.16348(10) 0.2803(2) 0.33597(13) 0.0884(9) Uani 1 1 d . . . O6 O -0.12834(9) 0.4138(2) 0.38372(12) 0.0779(8) Uani 1 1 d . . . O7 O 0.11357(8) 0.46707(19) 0.45098(10) 0.0654(7) Uani 1 1 d . . . O8 O 0.07593(10) 0.0432(2) 0.44143(11) 0.0787(8) Uani 1 1 d . . . O9 O 0.18052(13) 0.2739(2) 0.61380(12) 0.0997(10) Uani 1 1 d . . . O10 O 0.14522(10) 0.1260(2) 0.59016(11) 0.0824(8) Uani 1 1 d . . . O11 O 0.07587(12) 0.3794(2) 0.57701(12) 0.0942(9) Uani 1 1 d . . . O12 O 0.04675(10) 0.2271(2) 0.57648(11) 0.0796(8) Uani 1 1 d D . . O13 O -0.13161(10) 0.5329(2) 0.18319(12) 0.0852(8) Uani 1 1 d . . . O15 O 0.25754(13) 0.5076(3) 0.40449(17) 0.1196(12) Uani 1 1 d . . . O17 O 0.18355(12) 0.0495(3) 0.39581(14) 0.1055(10) Uani 1 1 d . . . O18 O -0.07271(10) 0.06631(19) 0.21949(11) 0.0797(8) Uani 1 1 d . . . C45 C 0.1970(6) 0.6153(12) 0.2556(12) 0.262(13) Uani 0.60 1 d PD C 1 H45A H 0.1727 0.6262 0.2212 0.315 Uiso 0.60 1 calc PR C 1 H45B H 0.1830 0.6137 0.2819 0.315 Uiso 0.60 1 calc PR C 1 C46 C 0.2300(5) 0.6981(9) 0.2675(7) 0.166(5) Uani 0.60 1 d PD C 1 H46A H 0.2389 0.7088 0.2375 0.199 Uiso 0.60 1 calc PR C 1 H46B H 0.2575 0.6802 0.2978 0.199 Uiso 0.60 1 calc PR C 1 Cl1 Cl 0.22378(14) 0.4995(3) 0.25555(14) 0.1408(11) Uani 0.60 1 d PD C 1 Cl2 Cl 0.20751(18) 0.8082(4) 0.2813(2) 0.1733(18) Uani 0.60 1 d PD C 1 C45' C 0.2249(9) 0.620(2) 0.2791(9) 0.174(9) Uani 0.40 1 d PDU C 2 H45C H 0.2168 0.5722 0.3013 0.208 Uiso 0.40 1 calc PR C 2 H45D H 0.2468 0.6667 0.3027 0.208 Uiso 0.40 1 calc PR C 2 C46' C 0.1829(9) 0.6758(16) 0.2478(11) 0.201(12) Uani 0.40 1 d PDU C 2 H46C H 0.1567 0.6359 0.2470 0.242 Uiso 0.40 1 calc PR C 2 H46D H 0.1816 0.6790 0.2116 0.242 Uiso 0.40 1 calc PR C 2 Cl1' Cl 0.2536(3) 0.5531(8) 0.2450(3) 0.235(4) Uani 0.40 1 d PD C 2 Cl2' Cl 0.1743(3) 0.7985(7) 0.2663(3) 0.1733(18) Uani 0.40 1 d PD C 2 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 0.057(2) 0.0446(17) 0.065(2) -0.0076(17) 0.0374(19) -0.0051(16) C2 0.0504(18) 0.0525(19) 0.056(2) -0.0051(15) 0.0287(16) -0.0056(15) C3 0.064(2) 0.056(2) 0.060(2) -0.0017(19) 0.032(2) -0.0082(18) C4 0.059(2) 0.0542(19) 0.052(2) -0.0008(16) 0.0289(17) -0.0068(16) C5 0.062(2) 0.065(2) 0.060(2) -0.004(2) 0.0324(19) -0.0104(19) C6 0.105(4) 0.141(4) 0.105(4) 0.009(3) 0.074(3) -0.021(3) C7 0.134(5) 0.142(5) 0.217(8) 0.065(5) 0.117(6) 0.003(4) C8 0.062(2) 0.070(2) 0.060(2) 0.000(2) 0.025(2) -0.009(2) C9 0.080(3) 0.087(3) 0.110(4) -0.004(3) 0.038(3) 0.017(2) C10 0.095(4) 0.154(5) 0.109(4) -0.009(4) 0.059(3) 0.013(3) C11 0.064(2) 0.065(2) 0.055(2) -0.0059(18) 0.0242(19) -0.0145(17) C12 0.070(2) 0.061(2) 0.056(2) 0.0032(17) 0.0311(19) -0.0031(18) C13 0.0499(19) 0.059(2) 0.048(2) -0.0008(16) 0.0162(16) -0.0058(15) C14 0.055(2) 0.061(2) 0.053(2) -0.0010(17) 0.0211(17) -0.0053(16) C15 0.069(2) 0.058(2) 0.060(2) -0.0047(18) 0.0264(19) -0.0082(18) C16 0.085(3) 0.068(2) 0.062(2) -0.0086(19) 0.040(2) -0.006(2) C17 0.081(3) 0.072(3) 0.067(3) 0.001(2) 0.044(2) -0.008(2) C18 0.058(2) 0.062(2) 0.059(2) 0.0039(17) 0.0272(18) -0.0045(16) C19 0.073(3) 0.071(3) 0.063(2) 0.0079(19) 0.032(2) 0.001(2) C20 0.150(5) 0.065(3) 0.106(4) -0.011(2) 0.070(4) 0.007(3) C21 0.065(2) 0.053(2) 0.059(2) 0.0037(17) 0.0242(19) -0.0111(17) C22 0.057(2) 0.0512(19) 0.067(2) -0.0127(17) 0.0323(19) -0.0063(16) C23 0.059(2) 0.061(2) 0.054(2) -0.0094(18) 0.0308(19) -0.0066(18) C24 0.062(2) 0.064(2) 0.054(2) -0.0036(17) 0.0278(18) -0.0006(17) C25 0.076(3) 0.058(2) 0.051(2) 0.0014(18) 0.028(2) 0.005(2) C26 0.062(2) 0.057(2) 0.054(2) -0.0080(16) 0.0299(18) -0.0074(16) C27 0.071(2) 0.074(3) 0.059(3) 0.001(2) 0.027(2) 0.002(2) C28 0.108(4) 0.102(3) 0.070(3) 0.025(2) 0.035(3) 0.005(3) C29 0.139(5) 0.159(6) 0.152(6) 0.071(5) 0.028(5) -0.044(4) C30 0.066(2) 0.071(3) 0.063(2) -0.004(2) 0.033(2) -0.003(2) C31 0.158(14) 0.145(10) 0.089(9) 0.062(7) 0.087(10) 0.094(10) C32 0.149(8) 0.081(5) 0.103(6) 0.004(5) 0.093(6) -0.008(5) C31' 0.070(7) 0.069(7) 0.058(7) 0.001(6) 0.037(6) -0.006(6) C32' 0.160(11) 0.179(11) 0.147(11) -0.001(8) 0.074(9) 0.026(8) C33 0.056(2) 0.080(2) 0.060(2) 0.0005(19) 0.0240(18) -0.0002(18) C34 0.070(2) 0.078(3) 0.071(3) -0.001(2) 0.030(2) 0.015(2) C35 0.048(2) 0.093(3) 0.062(2) -0.001(2) 0.0256(18) 0.0038(19) C36 0.059(2) 0.094(3) 0.060(2) -0.002(2) 0.0259(19) 0.013(2) C37 0.065(3) 0.110(4) 0.071(3) -0.010(3) 0.028(2) 0.017(2) C38 0.078(3) 0.139(5) 0.064(3) -0.008(3) 0.035(2) 0.005(3) C39 0.074(3) 0.130(4) 0.067(3) 0.009(3) 0.034(2) 0.000(3) C40 0.056(2) 0.104(3) 0.064(3) 0.004(2) 0.029(2) 0.004(2) C41 0.068(3) 0.125(4) 0.078(3) 0.014(3) 0.040(2) -0.004(3) C42 0.101(5) 0.114(5) 0.104(5) 0.008(4) 0.050(4) -0.018(4) C43 0.136(5) 0.144(5) 0.096(4) -0.042(3) 0.040(4) 0.036(4) C44 0.105(4) 0.074(3) 0.092(4) 0.006(3) 0.044(4) 0.007(3) F1 0.159(10) 0.062(4) 0.241(16) 0.022(8) 0.124(12) 0.026(6) F2 0.140(12) 0.100(8) 0.157(9) 0.029(7) -0.022(9) -0.046(8) F3 0.160(8) 0.102(6) 0.097(5) 0.017(4) 0.059(6) -0.030(6) F1' 0.21(2) 0.069(5) 0.38(4) 0.000(13) 0.23(3) -0.011(9) F2' 0.22(2) 0.169(17) 0.190(18) 0.102(15) 0.000(14) 0.013(11) F3' 0.219(15) 0.102(7) 0.219(15) -0.052(9) 0.138(14) -0.036(9) F4 0.184(8) 0.099(5) 0.162(9) 0.020(6) 0.109(8) -0.034(6) F5 0.115(6) 0.145(6) 0.120(5) -0.024(4) 0.036(5) -0.021(5) F6 0.084(5) 0.118(7) 0.167(7) -0.017(5) 0.051(4) 0.008(4) F4' 0.203(19) 0.24(3) 0.33(4) -0.14(3) 0.15(2) -0.091(18) F5' 0.27(3) 0.130(14) 0.24(2) 0.006(12) 0.22(2) -0.021(14) F6' 0.26(3) 0.143(14) 0.188(17) -0.001(13) 0.104(16) -0.054(15) N1 0.0561(17) 0.0484(15) 0.0566(18) -0.0026(13) 0.0275(15) -0.0086(13) N2 0.0656(18) 0.0577(16) 0.0523(18) -0.0049(14) 0.0284(15) -0.0138(14) N3 0.0650(17) 0.0516(16) 0.0532(18) -0.0023(14) 0.0259(15) -0.0062(14) N4 0.0621(18) 0.0542(16) 0.0523(18) -0.0038(14) 0.0271(15) -0.0094(14) N5 0.0572(17) 0.0542(16) 0.0540(17) -0.0037(13) 0.0287(14) -0.0049(13) N6 0.0554(17) 0.0715(19) 0.0532(18) 0.0008(15) 0.0259(15) -0.0009(15) N7 0.066(2) 0.0651(18) 0.0622(19) -0.0057(15) 0.0307(16) 0.0018(16) N8 0.0618(18) 0.0544(16) 0.0590(18) -0.0009(14) 0.0261(15) -0.0036(14) N9 0.067(2) 0.099(3) 0.078(2) 0.010(2) 0.0372(19) 0.0003(19) N10 0.0677(19) 0.0640(19) 0.070(2) 0.0048(15) 0.0355(17) -0.0049(16) O1 0.0728(16) 0.0516(13) 0.0765(17) 0.0000(12) 0.0438(14) -0.0063(12) O2 0.0843(18) 0.0584(16) 0.0796(19) -0.0120(13) 0.0326(15) -0.0001(13) O3 0.102(2) 0.091(2) 0.0763(19) -0.0287(16) 0.0551(17) -0.0262(16) O4 0.0784(17) 0.0895(18) 0.0720(18) -0.0003(14) 0.0473(15) -0.0254(15) O5 0.0616(17) 0.110(2) 0.096(2) -0.0266(18) 0.0320(16) -0.0140(16) O6 0.0724(17) 0.0731(17) 0.095(2) -0.0140(15) 0.0396(16) 0.0020(14) O7 0.0622(15) 0.0686(15) 0.0715(17) 0.0090(13) 0.0321(13) -0.0080(12) O8 0.0894(19) 0.0685(17) 0.0774(19) -0.0148(15) 0.0303(16) 0.0055(14) O9 0.126(3) 0.092(2) 0.0582(19) -0.0020(16) 0.0085(18) -0.0171(19) O10 0.092(2) 0.0804(19) 0.0676(19) 0.0131(15) 0.0215(16) -0.0095(15) O11 0.126(3) 0.092(2) 0.087(2) -0.0298(17) 0.065(2) -0.0322(19) O12 0.105(2) 0.0768(17) 0.0807(19) 0.0010(14) 0.0615(18) -0.0030(15) O13 0.078(2) 0.091(2) 0.087(2) 0.0141(16) 0.0326(17) 0.0096(16) O15 0.103(2) 0.142(3) 0.149(3) 0.006(2) 0.087(3) -0.010(2) O17 0.123(3) 0.107(3) 0.099(2) -0.0257(19) 0.056(2) 0.020(2) O18 0.114(2) 0.0611(16) 0.0783(19) -0.0102(13) 0.0531(17) -0.0087(14) C45 0.110(13) 0.32(3) 0.34(3) 0.09(3) 0.068(17) 0.040(18) C46 0.126(10) 0.134(11) 0.219(15) -0.009(10) 0.044(10) -0.023(8) Cl1 0.149(3) 0.145(2) 0.110(2) -0.0146(17) 0.027(2) 0.019(2) Cl2 0.237(6) 0.148(2) 0.130(3) -0.011(2) 0.064(4) 0.008(4) C45' 0.172(13) 0.176(13) 0.173(12) 0.005(9) 0.065(9) -0.005(9) C46' 0.212(15) 0.207(15) 0.204(14) 0.025(9) 0.099(10) 0.017(9) Cl1' 0.193(7) 0.352(12) 0.128(5) -0.047(6) 0.025(5) 0.078(7) Cl2' 0.237(6) 0.148(2) 0.130(3) -0.011(2) 0.064(4) 0.008(4) _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 O1 1.220(4) . ? C1 N2 1.343(4) . ? C1 N1 1.382(4) . ? C2 N1 1.441(4) . ? C2 N3 1.459(4) . ? C2 C5 1.554(5) . ? C2 C4 1.569(5) . ? C3 O2 1.208(4) . ? C3 N4 1.358(5) . ? C3 N3 1.400(5) . ? C4 N4 1.437(4) . ? C4 N2 1.445(4) . ? C4 C8 1.539(5) . ? C5 O3 1.181(4) . ? C5 O4 1.312(4) . ? C6 C7 1.429(8) . ? C6 O4 1.481(5) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 O5 1.182(4) . ? C8 O6 1.322(4) . ? C9 O6 1.438(5) . ? C9 C10 1.469(7) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 N4 1.446(4) . ? C11 C14 1.514(5) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 N2 1.455(5) . ? C12 C13 1.512(5) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C18 1.399(5) . ? C13 C14 1.403(5) . ? C14 C15 1.406(5) . ? C15 O18 1.366(4) . ? C15 C16 1.378(5) . ? C16 C17 1.365(5) . ? C16 H16 0.9300 . ? C17 C18 1.377(5) . ? C17 H17 0.9300 . ? C18 N10 1.431(5) . ? C19 O13 1.221(5) . ? C19 N10 1.332(5) . ? C19 C44 1.518(6) . ? C20 O18 1.418(5) . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 N8 1.416(4) . ? C21 N3 1.456(4) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 N5 1.455(4) . ? C22 N1 1.455(4) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 O7 1.210(4) . ? C23 N5 1.379(4) . ? C23 N6 1.387(5) . ? C24 N6 1.435(5) . ? C24 N7 1.444(5) . ? C24 C27 1.546(6) . ? C24 C26 1.564(5) . ? C25 O8 1.208(4) . ? C25 N7 1.347(5) . ? C25 N8 1.399(4) . ? C26 N8 1.452(4) . ? C26 N5 1.468(4) . ? C26 C30 1.539(5) . ? C27 O9 1.198(5) . ? C27 O10 1.300(5) . ? C28 C29 1.435(7) . ? C28 O10 1.445(5) . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 0.9600 . ? C30 O11 1.199(4) . ? C30 O12 1.304(4) . ? C31 C32 1.418(14) . ? C31 O12 1.522(12) . ? C31 H31A 0.9700 . ? C31 H31B 0.9700 . ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 0.9600 . ? C31' C32' 1.451(17) . ? C31' O12 1.488(14) . ? C31' H31C 0.9700 . ? C31' H31D 0.9700 . ? C32' H32D 0.9600 . ? C32' H32E 0.9600 . ? C32' H32F 0.9600 . ? C33 N6 1.449(4) . ? C33 C35 1.509(5) . ? C33 H33A 0.9700 . ? C33 H33B 0.9700 . ? C34 N7 1.458(5) . ? C34 C36 1.509(6) . ? C34 H34A 0.9700 . ? C34 H34B 0.9700 . ? C35 C40 1.388(5) . ? C35 C36 1.394(6) . ? C36 C37 1.414(6) . ? C37 O17 1.370(6) . ? C37 C38 1.387(7) . ? C38 C39 1.366(7) . ? C38 H38 0.9300 . ? C39 C40 1.379(6) . ? C39 H39 0.9300 . ? C40 N9 1.420(5) . ? C41 O15 1.195(5) . ? C41 N9 1.314(5) . ? C41 C42 1.519(8) . ? C42 F6 1.280(8) . ? C42 F5' 1.288(13) . ? C42 F4' 1.298(12) . ? C42 F4 1.301(9) . ? C42 F6' 1.327(13) . ? C42 F5 1.335(10) . ? C43 O17 1.427(6) . ? C43 H43A 0.9600 . ? C43 H43B 0.9600 . ? C43 H43C 0.9600 . ? C44 F2' 1.250(10) . ? C44 F1' 1.255(10) . ? C44 F2 1.257(9) . ? C44 F1 1.262(8) . ? C44 F3' 1.330(9) . ? C44 F3 1.333(8) . ? F4 Cl2 3.584(11) . ? F6' Cl2' 3.538(17) . ? N9 H9 0.8600 . ? N10 H10 0.8600 . ? C45 C46 1.461(13) . ? C45 Cl1 1.757(16) . ? C45 H45A 0.9700 . ? C45 H45B 0.9700 . ? C46 Cl2 1.728(12) . ? C46 H46A 0.9700 . ? C46 H46B 0.9700 . ? C45' C46' 1.474(14) . ? C45' Cl1' 1.753(17) . ? C45' H45C 0.9700 . ? C45' H45D 0.9700 . ? C46' Cl2' 1.763(18) . ? C46' H46C 0.9700 . ? C46' H46D 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 N2 126.1(3) . . ? O1 C1 N1 125.6(3) . . ? N2 C1 N1 108.3(3) . . ? N1 C2 N3 114.4(3) . . ? N1 C2 C5 112.9(3) . . ? N3 C2 C5 109.0(3) . . ? N1 C2 C4 102.7(2) . . ? N3 C2 C4 102.5(2) . . ? C5 C2 C4 114.9(3) . . ? O2 C3 N4 126.8(3) . . ? O2 C3 N3 124.4(3) . . ? N4 C3 N3 108.8(3) . . ? N4 C4 N2 112.8(3) . . ? N4 C4 C8 112.0(3) . . ? N2 C4 C8 108.9(3) . . ? N4 C4 C2 104.3(3) . . ? N2 C4 C2 102.7(2) . . ? C8 C4 C2 115.9(3) . . ? O3 C5 O4 125.7(3) . . ? O3 C5 C2 124.5(3) . . ? O4 C5 C2 109.6(3) . . ? C7 C6 O4 109.5(5) . . ? C7 C6 H6A 109.8 . . ? O4 C6 H6A 109.8 . . ? C7 C6 H6B 109.8 . . ? O4 C6 H6B 109.8 . . ? H6A C6 H6B 108.2 . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? O5 C8 O6 126.1(4) . . ? O5 C8 C4 124.0(4) . . ? O6 C8 C4 109.9(3) . . ? O6 C9 C10 112.6(4) . . ? O6 C9 H9A 109.1 . . ? C10 C9 H9A 109.1 . . ? O6 C9 H9B 109.1 . . ? C10 C9 H9B 109.1 . . ? H9A C9 H9B 107.8 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N4 C11 C14 117.1(3) . . ? N4 C11 H11A 108.0 . . ? C14 C11 H11A 108.0 . . ? N4 C11 H11B 108.0 . . ? C14 C11 H11B 108.0 . . ? H11A C11 H11B 107.3 . . ? N2 C12 C13 114.1(3) . . ? N2 C12 H12A 108.7 . . ? C13 C12 H12A 108.7 . . ? N2 C12 H12B 108.7 . . ? C13 C12 H12B 108.7 . . ? H12A C12 H12B 107.6 . . ? C18 C13 C14 118.6(3) . . ? C18 C13 C12 120.5(3) . . ? C14 C13 C12 120.8(3) . . ? C13 C14 C15 119.4(3) . . ? C13 C14 C11 122.5(3) . . ? C15 C14 C11 118.0(3) . . ? O18 C15 C16 123.3(3) . . ? O18 C15 C14 116.0(3) . . ? C16 C15 C14 120.7(3) . . ? C17 C16 C15 119.1(3) . . ? C17 C16 H16 120.5 . . ? C15 C16 H16 120.5 . . ? C16 C17 C18 122.0(3) . . ? C16 C17 H17 119.0 . . ? C18 C17 H17 119.0 . . ? C17 C18 C13 119.9(3) . . ? C17 C18 N10 117.4(3) . . ? C13 C18 N10 122.6(3) . . ? O13 C19 N10 125.8(4) . . ? O13 C19 C44 119.0(4) . . ? N10 C19 C44 115.2(4) . . ? O18 C20 H20A 109.5 . . ? O18 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? O18 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? N8 C21 N3 115.2(3) . . ? N8 C21 H21A 108.5 . . ? N3 C21 H21A 108.5 . . ? N8 C21 H21B 108.5 . . ? N3 C21 H21B 108.5 . . ? H21A C21 H21B 107.5 . . ? N5 C22 N1 115.5(3) . . ? N5 C22 H22A 108.4 . . ? N1 C22 H22A 108.4 . . ? N5 C22 H22B 108.4 . . ? N1 C22 H22B 108.4 . . ? H22A C22 H22B 107.5 . . ? O7 C23 N5 127.0(3) . . ? O7 C23 N6 124.5(3) . . ? N5 C23 N6 108.5(3) . . ? N6 C24 N7 113.4(3) . . ? N6 C24 C27 110.9(3) . . ? N7 C24 C27 112.0(3) . . ? N6 C24 C26 103.3(3) . . ? N7 C24 C26 102.3(3) . . ? C27 C24 C26 114.4(3) . . ? O8 C25 N7 127.3(3) . . ? O8 C25 N8 124.7(4) . . ? N7 C25 N8 107.9(3) . . ? N8 C26 N5 114.9(3) . . ? N8 C26 C30 116.0(3) . . ? N5 C26 C30 110.2(3) . . ? N8 C26 C24 101.5(3) . . ? N5 C26 C24 101.6(3) . . ? C30 C26 C24 111.4(3) . . ? O9 C27 O10 126.7(4) . . ? O9 C27 C24 123.5(4) . . ? O10 C27 C24 109.8(3) . . ? C29 C28 O10 108.9(4) . . ? C29 C28 H28A 109.9 . . ? O10 C28 H28A 109.9 . . ? C29 C28 H28B 109.9 . . ? O10 C28 H28B 109.9 . . ? H28A C28 H28B 108.3 . . ? C28 C29 H29A 109.5 . . ? C28 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C28 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? O11 C30 O12 125.3(4) . . ? O11 C30 C26 120.3(3) . . ? O12 C30 C26 114.4(3) . . ? C32 C31 O12 107.8(10) . . ? C32 C31 H31A 110.1 . . ? O12 C31 H31A 110.1 . . ? C32 C31 H31B 110.1 . . ? O12 C31 H31B 110.1 . . ? H31A C31 H31B 108.5 . . ? C32' C31' O12 101.3(13) . . ? C32' C31' H31C 111.5 . . ? O12 C31' H31C 111.5 . . ? C32' C31' H31D 111.5 . . ? O12 C31' H31D 111.5 . . ? H31C C31' H31D 109.3 . . ? C31' C32' H32D 109.5 . . ? C31' C32' H32E 109.5 . . ? H32D C32' H32E 109.5 . . ? C31' C32' H32F 109.5 . . ? H32D C32' H32F 109.5 . . ? H32E C32' H32F 109.5 . . ? N6 C33 C35 114.1(3) . . ? N6 C33 H33A 108.7 . . ? C35 C33 H33A 108.7 . . ? N6 C33 H33B 108.7 . . ? C35 C33 H33B 108.7 . . ? H33A C33 H33B 107.6 . . ? N7 C34 C36 111.8(3) . . ? N7 C34 H34A 109.3 . . ? C36 C34 H34A 109.3 . . ? N7 C34 H34B 109.3 . . ? C36 C34 H34B 109.3 . . ? H34A C34 H34B 107.9 . . ? C40 C35 C36 120.3(4) . . ? C40 C35 C33 120.2(4) . . ? C36 C35 C33 119.5(3) . . ? C35 C36 C37 118.9(4) . . ? C35 C36 C34 120.7(3) . . ? C37 C36 C34 120.3(4) . . ? O17 C37 C38 125.5(4) . . ? O17 C37 C36 114.9(4) . . ? C38 C37 C36 119.5(5) . . ? C39 C38 C37 120.2(4) . . ? C39 C38 H38 119.9 . . ? C37 C38 H38 119.9 . . ? C38 C39 C40 121.4(4) . . ? C38 C39 H39 119.3 . . ? C40 C39 H39 119.3 . . ? C39 C40 C35 119.4(4) . . ? C39 C40 N9 122.3(4) . . ? C35 C40 N9 118.1(4) . . ? O15 C41 N9 126.1(5) . . ? O15 C41 C42 119.7(5) . . ? N9 C41 C42 113.9(4) . . ? F6 C42 F5' 17.3(15) . . ? F6 C42 F4' 123.7(15) . . ? F5' C42 F4' 108.4(13) . . ? F6 C42 F4 108.4(8) . . ? F5' C42 F4 115.2(14) . . ? F4' C42 F4 77.0(13) . . ? F6 C42 F6' 92.6(16) . . ? F5' C42 F6' 105.7(13) . . ? F4' C42 F6' 105.0(11) . . ? F4 C42 F6' 28.0(12) . . ? F6 C42 F5 105.6(8) . . ? F5' C42 F5 88.3(13) . . ? F4' C42 F5 30.8(13) . . ? F4 C42 F5 106.7(9) . . ? F6' C42 F5 134.3(13) . . ? F6 C42 C41 114.0(7) . . ? F5' C42 C41 120.1(12) . . ? F4' C42 C41 113.0(15) . . ? F4 C42 C41 114.9(8) . . ? F6' C42 C41 103.3(15) . . ? F5 C42 C41 106.5(7) . . ? O17 C43 H43A 109.5 . . ? O17 C43 H43B 109.5 . . ? H43A C43 H43B 109.5 . . ? O17 C43 H43C 109.5 . . ? H43A C43 H43C 109.5 . . ? H43B C43 H43C 109.5 . . ? F2' C44 F1' 112.2(9) . . ? F2' C44 F2 131.8(10) . . ? F1' C44 F2 38.7(9) . . ? F2' C44 F1 49.2(11) . . ? F1' C44 F1 129.9(9) . . ? F2 C44 F1 112.2(8) . . ? F2' C44 F3' 104.0(10) . . ? F1' C44 F3' 102.3(8) . . ? F2 C44 F3' 65.7(8) . . ? F1 C44 F3' 56.4(7) . . ? F2' C44 F3 56.0(13) . . ? F1' C44 F3 66.1(10) . . ? F2 C44 F3 103.3(8) . . ? F1 C44 F3 103.2(8) . . ? F3' C44 F3 143.7(7) . . ? F2' C44 C19 113.9(9) . . ? F1' C44 C19 116.5(8) . . ? F2 C44 C19 114.2(6) . . ? F1 C44 C19 113.2(6) . . ? F3' C44 C19 106.3(7) . . ? F3 C44 C19 109.7(5) . . ? C42 F4 Cl2 145.4(9) . . ? C42 F6' Cl2' 169.7(16) . . ? C1 N1 C2 112.4(3) . . ? C1 N1 C22 120.9(3) . . ? C2 N1 C22 126.7(3) . . ? C1 N2 C4 113.4(3) . . ? C1 N2 C12 123.7(3) . . ? C4 N2 C12 122.8(3) . . ? C3 N3 C21 120.1(3) . . ? C3 N3 C2 111.6(3) . . ? C21 N3 C2 124.0(3) . . ? C3 N4 C4 112.6(3) . . ? C3 N4 C11 121.4(3) . . ? C4 N4 C11 122.6(3) . . ? C23 N5 C22 118.0(3) . . ? C23 N5 C26 111.3(3) . . ? C22 N5 C26 123.5(3) . . ? C23 N6 C24 110.7(3) . . ? C23 N6 C33 120.1(3) . . ? C24 N6 C33 118.4(3) . . ? C25 N7 C24 112.5(3) . . ? C25 N7 C34 124.2(3) . . ? C24 N7 C34 122.4(3) . . ? C25 N8 C21 120.0(3) . . ? C25 N8 C26 111.1(3) . . ? C21 N8 C26 127.0(3) . . ? C41 N9 C40 126.5(4) . . ? C41 N9 H9 116.7 . . ? C40 N9 H9 116.7 . . ? C19 N10 C18 126.2(3) . . ? C19 N10 H10 116.9 . . ? C18 N10 H10 116.9 . . ? C5 O4 C6 116.6(3) . . ? C8 O6 C9 119.4(3) . . ? C27 O10 C28 117.1(3) . . ? C30 O12 C31' 114.2(6) . . ? C30 O12 C31 114.1(6) . . ? C31' O12 C31 17.7(10) . . ? C37 O17 C43 118.0(4) . . ? C15 O18 C20 118.8(3) . . ? C46 C45 Cl1 111.6(11) . . ? C46 C45 H45A 109.3 . . ? Cl1 C45 H45A 109.3 . . ? C46 C45 H45B 109.3 . . ? Cl1 C45 H45B 109.3 . . ? H45A C45 H45B 108.0 . . ? C45 C46 Cl2 112.3(11) . . ? C45 C46 H46A 109.1 . . ? Cl2 C46 H46A 109.1 . . ? C45 C46 H46B 109.1 . . ? Cl2 C46 H46B 109.1 . . ? H46A C46 H46B 107.9 . . ? C46 Cl2 F4 85.8(7) . . ? C46' C45' Cl1' 118.2(17) . . ? C46' C45' H45C 107.8 . . ? Cl1' C45' H45C 107.8 . . ? C46' C45' H45D 107.8 . . ? Cl1' C45' H45D 107.8 . . ? H45C C45' H45D 107.1 . . ? C45' C46' Cl2' 120.3(19) . . ? C45' C46' H46C 107.2 . . ? Cl2' C46' H46C 107.2 . . ? C45' C46' H46D 107.2 . . ? Cl2' C46' H46D 107.2 . . ? H46C C46' H46D 106.9 . . ? C46' Cl2' F6' 81.7(11) . . ? 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 N1 C2 C4 N4 124.2(2) . . . . ? N3 C2 C4 N4 5.3(3) . . . . ? C5 C2 C4 N4 -112.9(3) . . . . ? N1 C2 C4 N2 6.3(3) . . . . ? N3 C2 C4 N2 -112.6(3) . . . . ? C5 C2 C4 N2 129.3(3) . . . . ? N1 C2 C4 C8 -112.2(3) . . . . ? N3 C2 C4 C8 128.9(3) . . . . ? C5 C2 C4 C8 10.8(4) . . . . ? N1 C2 C5 O3 -11.6(5) . . . . ? N3 C2 C5 O3 116.7(4) . . . . ? C4 C2 C5 O3 -129.0(4) . . . . ? N1 C2 C5 O4 172.9(3) . . . . ? N3 C2 C5 O4 -58.8(4) . . . . ? C4 C2 C5 O4 55.6(4) . . . . ? N4 C4 C8 O5 -7.5(5) . . . . ? N2 C4 C8 O5 117.9(4) . . . . ? C2 C4 C8 O5 -127.0(4) . . . . ? N4 C4 C8 O6 172.9(3) . . . . ? N2 C4 C8 O6 -61.7(4) . . . . ? C2 C4 C8 O6 53.4(4) . . . . ? N2 C12 C13 C18 -128.9(3) . . . . ? N2 C12 C13 C14 51.6(4) . . . . ? C18 C13 C14 C15 4.2(5) . . . . ? C12 C13 C14 C15 -176.3(3) . . . . ? C18 C13 C14 C11 -172.6(3) . . . . ? C12 C13 C14 C11 6.8(5) . . . . ? N4 C11 C14 C13 -59.5(5) . . . . ? N4 C11 C14 C15 123.6(4) . . . . ? C13 C14 C15 O18 176.3(3) . . . . ? C11 C14 C15 O18 -6.7(5) . . . . ? C13 C14 C15 C16 -3.3(5) . . . . ? C11 C14 C15 C16 173.7(3) . . . . ? O18 C15 C16 C17 -179.9(3) . . . . ? C14 C15 C16 C17 -0.3(6) . . . . ? C15 C16 C17 C18 3.0(6) . . . . ? C16 C17 C18 C13 -2.0(6) . . . . ? C16 C17 C18 N10 176.6(3) . . . . ? C14 C13 C18 C17 -1.7(5) . . . . ? C12 C13 C18 C17 178.9(3) . . . . ? C14 C13 C18 N10 179.8(3) . . . . ? C12 C13 C18 N10 0.3(5) . . . . ? N6 C24 C26 N8 138.7(3) . . . . ? N7 C24 C26 N8 20.7(3) . . . . ? C27 C24 C26 N8 -100.6(3) . . . . ? N6 C24 C26 N5 20.0(3) . . . . ? N7 C24 C26 N5 -98.0(3) . . . . ? C27 C24 C26 N5 140.7(3) . . . . ? N6 C24 C26 C30 -97.3(3) . . . . ? N7 C24 C26 C30 144.7(3) . . . . ? C27 C24 C26 C30 23.4(4) . . . . ? N6 C24 C27 O9 11.7(5) . . . . ? N7 C24 C27 O9 139.5(4) . . . . ? C26 C24 C27 O9 -104.7(5) . . . . ? N6 C24 C27 O10 -168.4(3) . . . . ? N7 C24 C27 O10 -40.7(4) . . . . ? C26 C24 C27 O10 75.2(4) . . . . ? N8 C26 C30 O11 -170.0(4) . . . . ? N5 C26 C30 O11 -37.4(5) . . . . ? C24 C26 C30 O11 74.6(5) . . . . ? N8 C26 C30 O12 11.1(5) . . . . ? N5 C26 C30 O12 143.7(3) . . . . ? C24 C26 C30 O12 -104.3(4) . . . . ? N6 C33 C35 C40 111.0(4) . . . . ? N6 C33 C35 C36 -70.0(5) . . . . ? C40 C35 C36 C37 5.6(5) . . . . ? C33 C35 C36 C37 -173.5(3) . . . . ? C40 C35 C36 C34 -171.5(3) . . . . ? C33 C35 C36 C34 9.5(5) . . . . ? N7 C34 C36 C35 54.0(5) . . . . ? N7 C34 C36 C37 -123.0(4) . . . . ? C35 C36 C37 O17 176.7(3) . . . . ? C34 C36 C37 O17 -6.3(5) . . . . ? C35 C36 C37 C38 -2.6(6) . . . . ? C34 C36 C37 C38 174.4(4) . . . . ? O17 C37 C38 C39 179.3(4) . . . . ? C36 C37 C38 C39 -1.6(6) . . . . ? C37 C38 C39 C40 2.9(7) . . . . ? C38 C39 C40 C35 0.1(6) . . . . ? C38 C39 C40 N9 -176.5(4) . . . . ? C36 C35 C40 C39 -4.4(6) . . . . ? C33 C35 C40 C39 174.6(4) . . . . ? C36 C35 C40 N9 172.3(3) . . . . ? C33 C35 C40 N9 -8.6(5) . . . . ? O15 C41 C42 F6 162.8(7) . . . . ? N9 C41 C42 F6 -22.1(9) . . . . ? O15 C41 C42 F5' -179.0(13) . . . . ? N9 C41 C42 F5' -3.9(14) . . . . ? O15 C41 C42 F4' -49.1(15) . . . . ? N9 C41 C42 F4' 126.0(13) . . . . ? O15 C41 C42 F4 36.8(10) . . . . ? N9 C41 C42 F4 -148.1(8) . . . . ? O15 C41 C42 F6' 63.8(13) . . . . ? N9 C41 C42 F6' -121.1(12) . . . . ? O15 C41 C42 F5 -81.2(7) . . . . ? N9 C41 C42 F5 94.0(7) . . . . ? O13 C19 C44 F2' -45(2) . . . . ? N10 C19 C44 F2' 137(2) . . . . ? O13 C19 C44 F1' -177.9(17) . . . . ? N10 C19 C44 F1' 3.9(17) . . . . ? O13 C19 C44 F2 139.2(13) . . . . ? N10 C19 C44 F2 -39.1(13) . . . . ? O13 C19 C44 F1 9.2(13) . . . . ? N10 C19 C44 F1 -169.1(12) . . . . ? O13 C19 C44 F3' 69.0(16) . . . . ? N10 C19 C44 F3' -109.3(15) . . . . ? O13 C19 C44 F3 -105.5(9) . . . . ? N10 C19 C44 F3 76.3(10) . . . . ? F6 C42 F4 Cl2 -73.2(16) . . . . ? F5' C42 F4 Cl2 -90.4(17) . . . . ? F4' C42 F4 Cl2 165.2(19) . . . . ? F6' C42 F4 Cl2 -15(3) . . . . ? F5 C42 F4 Cl2 173.5(12) . . . . ? C41 C42 F4 Cl2 55.7(16) . . . . ? F6 C42 F6' Cl2' -65(11) . . . . ? F5' C42 F6' Cl2' -77(11) . . . . ? F4' C42 F6' Cl2' 169(10) . . . . ? F4 C42 F6' Cl2' 169(14) . . . . ? C41 C42 F6' Cl2' 50(11) . . . . ? O1 C1 N1 C2 -176.3(3) . . . . ? N2 C1 N1 C2 3.0(3) . . . . ? O1 C1 N1 C22 0.7(5) . . . . ? N2 C1 N1 C22 -180.0(3) . . . . ? N3 C2 N1 C1 104.3(3) . . . . ? C5 C2 N1 C1 -130.3(3) . . . . ? C4 C2 N1 C1 -5.9(3) . . . . ? N3 C2 N1 C22 -72.5(4) . . . . ? C5 C2 N1 C22 52.9(4) . . . . ? C4 C2 N1 C22 177.3(3) . . . . ? N5 C22 N1 C1 -106.8(3) . . . . ? N5 C22 N1 C2 69.8(4) . . . . ? O1 C1 N2 C4 -179.0(3) . . . . ? N1 C1 N2 C4 1.7(4) . . . . ? O1 C1 N2 C12 2.1(5) . . . . ? N1 C1 N2 C12 -177.2(3) . . . . ? N4 C4 N2 C1 -116.8(3) . . . . ? C8 C4 N2 C1 118.2(3) . . . . ? C2 C4 N2 C1 -5.2(3) . . . . ? N4 C4 N2 C12 62.1(4) . . . . ? C8 C4 N2 C12 -62.9(4) . . . . ? C2 C4 N2 C12 173.7(3) . . . . ? C13 C12 N2 C1 99.7(4) . . . . ? C13 C12 N2 C4 -79.1(4) . . . . ? O2 C3 N3 C21 -21.8(5) . . . . ? N4 C3 N3 C21 158.3(3) . . . . ? O2 C3 N3 C2 -179.4(3) . . . . ? N4 C3 N3 C2 0.7(3) . . . . ? N8 C21 N3 C3 118.8(3) . . . . ? N8 C21 N3 C2 -86.5(4) . . . . ? N1 C2 N3 C3 -114.1(3) . . . . ? C5 C2 N3 C3 118.5(3) . . . . ? C4 C2 N3 C3 -3.7(3) . . . . ? N1 C2 N3 C21 89.3(4) . . . . ? C5 C2 N3 C21 -38.1(4) . . . . ? C4 C2 N3 C21 -160.3(3) . . . . ? O2 C3 N4 C4 -176.8(3) . . . . ? N3 C3 N4 C4 3.2(4) . . . . ? O2 C3 N4 C11 -17.3(5) . . . . ? N3 C3 N4 C11 162.6(3) . . . . ? N2 C4 N4 C3 105.3(3) . . . . ? C8 C4 N4 C3 -131.4(3) . . . . ? C2 C4 N4 C3 -5.4(3) . . . . ? N2 C4 N4 C11 -53.9(4) . . . . ? C8 C4 N4 C11 69.4(4) . . . . ? C2 C4 N4 C11 -164.5(3) . . . . ? C14 C11 N4 C3 -87.7(4) . . . . ? C14 C11 N4 C4 69.6(4) . . . . ? O7 C23 N5 C22 -26.3(5) . . . . ? N6 C23 N5 C22 153.3(3) . . . . ? O7 C23 N5 C26 -177.7(3) . . . . ? N6 C23 N5 C26 1.9(3) . . . . ? N1 C22 N5 C23 127.5(3) . . . . ? N1 C22 N5 C26 -84.8(4) . . . . ? N8 C26 N5 C23 -122.5(3) . . . . ? C30 C26 N5 C23 104.3(3) . . . . ? C24 C26 N5 C23 -13.8(3) . . . . ? N8 C26 N5 C22 88.0(4) . . . . ? C30 C26 N5 C22 -45.2(4) . . . . ? C24 C26 N5 C22 -163.3(3) . . . . ? O7 C23 N6 C24 -167.8(3) . . . . ? N5 C23 N6 C24 12.6(4) . . . . ? O7 C23 N6 C33 -24.0(5) . . . . ? N5 C23 N6 C33 156.4(3) . . . . ? N7 C24 N6 C23 89.4(3) . . . . ? C27 C24 N6 C23 -143.7(3) . . . . ? C26 C24 N6 C23 -20.6(3) . . . . ? N7 C24 N6 C33 -55.1(4) . . . . ? C27 C24 N6 C33 71.9(4) . . . . ? C26 C24 N6 C33 -165.1(3) . . . . ? C35 C33 N6 C23 -63.3(4) . . . . ? C35 C33 N6 C24 77.8(4) . . . . ? O8 C25 N7 C24 -172.7(4) . . . . ? N8 C25 N7 C24 7.4(4) . . . . ? O8 C25 N7 C34 -3.3(6) . . . . ? N8 C25 N7 C34 176.7(3) . . . . ? N6 C24 N7 C25 -128.6(3) . . . . ? C27 C24 N7 C25 105.0(3) . . . . ? C26 C24 N7 C25 -18.1(4) . . . . ? N6 C24 N7 C34 61.8(4) . . . . ? C27 C24 N7 C34 -64.6(4) . . . . ? C26 C24 N7 C34 172.4(3) . . . . ? C36 C34 N7 C25 111.1(4) . . . . ? C36 C34 N7 C24 -80.5(4) . . . . ? O8 C25 N8 C21 -6.9(5) . . . . ? N7 C25 N8 C21 173.0(3) . . . . ? O8 C25 N8 C26 -172.0(3) . . . . ? N7 C25 N8 C26 7.9(4) . . . . ? N3 C21 N8 C25 -92.1(4) . . . . ? N3 C21 N8 C26 70.4(4) . . . . ? N5 C26 N8 C25 90.6(3) . . . . ? C30 C26 N8 C25 -138.9(3) . . . . ? C24 C26 N8 C25 -18.1(3) . . . . ? N5 C26 N8 C21 -73.2(4) . . . . ? C30 C26 N8 C21 57.2(5) . . . . ? C24 C26 N8 C21 178.1(3) . . . . ? O15 C41 N9 C40 1.6(7) . . . . ? C42 C41 N9 C40 -173.2(4) . . . . ? C39 C40 N9 C41 -46.4(6) . . . . ? C35 C40 N9 C41 137.0(4) . . . . ? O13 C19 N10 C18 5.5(6) . . . . ? C44 C19 N10 C18 -176.3(4) . . . . ? C17 C18 N10 C19 123.3(4) . . . . ? C13 C18 N10 C19 -58.0(5) . . . . ? O3 C5 O4 C6 -1.9(6) . . . . ? C2 C5 O4 C6 173.5(3) . . . . ? C7 C6 O4 C5 172.3(4) . . . . ? O5 C8 O6 C9 -4.1(6) . . . . ? C4 C8 O6 C9 175.5(3) . . . . ? C10 C9 O6 C8 83.6(5) . . . . ? O9 C27 O10 C28 0.8(6) . . . . ? C24 C27 O10 C28 -179.0(3) . . . . ? C29 C28 O10 C27 173.3(5) . . . . ? O11 C30 O12 C31' 12.4(9) . . . . ? C26 C30 O12 C31' -168.8(8) . . . . ? O11 C30 O12 C31 -7.0(8) . . . . ? C26 C30 O12 C31 171.8(7) . . . . ? C32' C31' O12 C30 -115.5(13) . . . . ? C32' C31' O12 C31 -22(3) . . . . ? C32 C31 O12 C30 -179.9(8) . . . . ? C32 C31 O12 C31' 86(4) . . . . ? C38 C37 O17 C43 -3.8(7) . . . . ? C36 C37 O17 C43 177.0(4) . . . . ? C16 C15 O18 C20 3.2(6) . . . . ? C14 C15 O18 C20 -176.4(4) . . . . ? Cl1 C45 C46 Cl2 -167.5(12) . . . . ? C45 C46 Cl2 F4 79.1(18) . . . . ? C42 F4 Cl2 C46 -65.8(15) . . . . ? Cl1' C45' C46' Cl2' -136(2) . . . . ? C45' C46' Cl2' F6' -44(3) . . . . ? C42 F6' Cl2' C46' -51(11) . . . . ? 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 N10 H10 O1 0.86 2.18 2.885(4) 138.6 2 N9 H9 O7 0.86 2.18 2.958(4) 149.8 . _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.741 _refine_diff_density_min -0.479 _refine_diff_density_rms 0.060 # start Validation Reply Form _vrf_PLAT242_f__cf3-4ucc_work_050807dm ; PROBLEM: Check Low Ueq as Compared to Neighbors for C42 RESPONSE: The problem should be induced by the disorder. ; _vrf_PLAT230_f__cf3-4ucc_work_050807dm ; PROBLEM: Hirshfeld Test Diff for C31 -- C32 .. 7.49 su RESPONSE: The problem should be induced by the disorder. ;