# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Masahide Tominaga' _publ_contact_author_email TOMINAGAM@KPH.BUNRI-U.AC.JP _publ_section_title ; Hydrogen-bonded networks formed from tri- and tetrasubstituted adamantanes bearing dimethoxyphenol moieties and their 1,3,5-trinitrobenzene complexes via charge-transfer interactions ; loop_ _publ_author_name 'Masahide Tominaga' 'Isao Azumaya' 'Kosuke Katagiri' # Attachment '740184.cif' data_a0906111kka _database_code_depnum_ccdc_archive 'CCDC 740184' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C36 H42 Cl6 O9' _chemical_formula_weight 831.40 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1)/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.8585(6) _cell_length_b 14.0448(8) _cell_length_c 28.6911(17) _cell_angle_alpha 90.00 _cell_angle_beta 99.0050(10) _cell_angle_gamma 90.00 _cell_volume 3923.6(4) _cell_formula_units_Z 4 _cell_measurement_temperature 120 _cell_measurement_reflns_used 8573 _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 27.02 _exptl_crystal_description prismatic _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.35 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.407 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1728 _exptl_absorpt_coefficient_mu 0.489 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8098 _exptl_absorpt_correction_T_max 0.8474 _exptl_absorpt_process_details ; SADABS Sheldrick 1996 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 120 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEXII CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.333 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18927 _diffrn_reflns_av_R_equivalents 0.0147 _diffrn_reflns_av_sigmaI/netI 0.0204 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 2.04 _diffrn_reflns_theta_max 27.20 _reflns_number_total 7914 _reflns_number_gt 6600 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2006)' _computing_cell_refinement 'APEX2 (Bruker AXS, 2006)' _computing_data_reduction 'SAINT (Bruker AXS, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XSHEL (Bruker AXS,2002)' _computing_publication_material 'XCIF (Bruker AXS, 2001)' _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^)+(0.1556P)^2^+8.4404P] 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 7914 _refine_ls_number_parameters 488 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0927 _refine_ls_R_factor_gt 0.0826 _refine_ls_wR_factor_ref 0.2585 _refine_ls_wR_factor_gt 0.2495 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.070 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl2 Cl 0.4094(3) 0.8468(2) 0.40695(15) 0.0801(12) Uani 0.690(10) 1 d P A 1 Cl3 Cl 0.1418(3) 0.76044(19) 0.40601(11) 0.0457(7) Uani 0.690(10) 1 d P A 1 Cl2B Cl 0.463(3) 0.8280(9) 0.4207(5) 0.296(15) Uani 0.310(10) 1 d P A 2 Cl3B Cl 0.183(2) 0.7673(14) 0.4078(4) 0.185(9) Uani 0.310(10) 1 d P A 2 O5 O 0.0808(2) 0.74731(15) 0.23097(7) 0.0175(5) Uani 1 1 d . . . O2 O 0.1463(2) 0.04118(16) 0.12144(8) 0.0226(5) Uani 1 1 d . . . O1 O 0.0407(2) -0.06844(15) 0.18372(8) 0.0209(5) Uani 1 1 d . . . H1 H 0.0242 -0.1003 0.2070 0.031 Uiso 1 1 calc R . . O3 O 0.0799(2) -0.02920(15) 0.27437(8) 0.0221(5) Uani 1 1 d . . . O4 O 0.0876(3) 0.76061(16) 0.13611(8) 0.0294(6) Uani 1 1 d . . . H4 H 0.0769 0.8064 0.1540 0.044 Uiso 1 1 calc R . . O9 O 0.2400(3) 0.4346(2) 0.46376(8) 0.0327(6) Uani 1 1 d . . . O8 O 0.6965(3) 0.3423(2) 0.48394(9) 0.0415(7) Uani 1 1 d . . . O7 O 0.4730(3) 0.3909(2) 0.51831(8) 0.0381(7) Uani 1 1 d . . . H7 H 0.4042 0.4201 0.5250 0.057 Uiso 1 1 calc R . . O6 O 0.2127(4) 0.6329(2) 0.09180(9) 0.0440(8) Uani 1 1 d . . . C16 C 0.0866(3) 0.7415(2) 0.28115(10) 0.0167(6) Uani 1 1 d . . . H16A H 0.0462 0.6811 0.2892 0.025 Uiso 1 1 calc R . . H16B H 0.0349 0.7946 0.2920 0.025 Uiso 1 1 calc R . . H16C H 0.1825 0.7448 0.2965 0.025 Uiso 1 1 calc R . . C5 C 0.2088(3) 0.1167(2) 0.26348(10) 0.0164(6) Uani 1 1 d . . . H5 H 0.2215 0.1318 0.2962 0.020 Uiso 1 1 calc R . . C1 C 0.1145(3) 0.0121(2) 0.19953(11) 0.0165(6) Uani 1 1 d . . . C21 C 0.3392(3) 0.4047(2) 0.39142(11) 0.0194(6) Uani 1 1 d . . . H21 H 0.2557 0.4191 0.3713 0.023 Uiso 1 1 calc R . . C25 C 0.3457(3) 0.2655(2) 0.24842(10) 0.0144(6) Uani 1 1 d U . . C28 C 0.3738(3) 0.4570(2) 0.29275(10) 0.0151(6) Uani 1 1 d U . . H28A H 0.2820 0.4646 0.3022 0.018 Uiso 1 1 calc R . . H28B H 0.4278 0.5151 0.3026 0.018 Uiso 1 1 calc R . . C27 C 0.3576(3) 0.4468(2) 0.23856(10) 0.0150(6) Uani 1 1 d U . . C26 C 0.2735(3) 0.3550(2) 0.22446(10) 0.0140(6) Uani 1 1 d U . . H26A H 0.1813 0.3613 0.2338 0.017 Uiso 1 1 calc R . . H26B H 0.2612 0.3472 0.1898 0.017 Uiso 1 1 calc R . . C6 C 0.1361(3) 0.0353(2) 0.24699(11) 0.0166(6) Uani 1 1 d . . . C4 C 0.2628(3) 0.1758(2) 0.23222(10) 0.0148(6) Uani 1 1 d . . . C9 C 0.1495(3) 0.6864(2) 0.16231(11) 0.0210(7) Uani 1 1 d . . . C30 C 0.3609(3) 0.2796(2) 0.30224(10) 0.0150(6) Uani 1 1 d . . . H30A H 0.4064 0.2231 0.3183 0.018 Uiso 1 1 calc R . . H30B H 0.2687 0.2854 0.3115 0.018 Uiso 1 1 calc R . . C3 C 0.2423(3) 0.1516(2) 0.18406(11) 0.0165(6) Uani 1 1 d . . . H3 H 0.2791 0.1914 0.1624 0.020 Uiso 1 1 calc R . . C10 C 0.1488(3) 0.6764(2) 0.21057(10) 0.0157(6) Uani 1 1 d . . . C2 C 0.1690(3) 0.0705(2) 0.16761(10) 0.0169(6) Uani 1 1 d . . . C19 C 0.5773(3) 0.3585(2) 0.40230(11) 0.0209(6) Uani 1 1 d . . . H19 H 0.6574 0.3419 0.3895 0.025 Uiso 1 1 calc R . . C29 C 0.4462(3) 0.3698(2) 0.31835(10) 0.0149(6) Uani 1 1 d U . . C20 C 0.4557(3) 0.3793(2) 0.37202(10) 0.0170(6) Uani 1 1 d . . . C11 C 0.2161(3) 0.6000(2) 0.23543(10) 0.0150(6) Uani 1 1 d . . . H11 H 0.2157 0.5947 0.2684 0.018 Uiso 1 1 calc R . . C13 C 0.2814(4) 0.5406(2) 0.16380(11) 0.0241(7) Uani 1 1 d . . . H13 H 0.3245 0.4936 0.1474 0.029 Uiso 1 1 calc R . . C12 C 0.2836(3) 0.5316(2) 0.21251(11) 0.0169(6) Uani 1 1 d . . . C31 C 0.4905(3) 0.2583(2) 0.23452(11) 0.0177(6) Uani 1 1 d . . . H31A H 0.5384 0.2018 0.2498 0.021 Uiso 1 1 calc R . . H31B H 0.4825 0.2504 0.1999 0.021 Uiso 1 1 calc R . . C32 C 0.5022(3) 0.4354(2) 0.22503(11) 0.0179(6) Uani 1 1 d . . . H32A H 0.4947 0.4276 0.1904 0.021 Uiso 1 1 calc R . . H32B H 0.5572 0.4932 0.2343 0.021 Uiso 1 1 calc R . . C14 C 0.2169(4) 0.6175(2) 0.13930(11) 0.0267(7) Uani 1 1 d . . . C33 C 0.5880(3) 0.3595(2) 0.30349(11) 0.0181(6) Uani 1 1 d . . . H33A H 0.6353 0.3031 0.3191 0.022 Uiso 1 1 calc R . . H33B H 0.6442 0.4164 0.3136 0.022 Uiso 1 1 calc R . . C34 C 0.5742(3) 0.3483(2) 0.24987(11) 0.0183(6) Uani 1 1 d . . . H34 H 0.6678 0.3420 0.2408 0.022 Uiso 1 1 calc R . . C18 C 0.5821(4) 0.3618(3) 0.45126(12) 0.0263(7) Uani 1 1 d . . . C23 C 0.8241(4) 0.3365(3) 0.46761(12) 0.0274(7) Uani 1 1 d . . . H23A H 0.8260 0.2792 0.4482 0.041 Uiso 1 1 calc R . . H23B H 0.8983 0.3333 0.4946 0.041 Uiso 1 1 calc R . . H23C H 0.8366 0.3929 0.4486 0.041 Uiso 1 1 calc R . . C22 C 0.3457(3) 0.4090(2) 0.44000(12) 0.0234(7) Uani 1 1 d . . . C17 C 0.4663(4) 0.3872(3) 0.47009(11) 0.0266(7) Uani 1 1 d . . . C8 C 0.0986(4) -0.0123(2) 0.32409(11) 0.0262(7) Uani 1 1 d . . . H8A H 0.1969 -0.0119 0.3367 0.039 Uiso 1 1 calc R . . H8B H 0.0532 -0.0627 0.3395 0.039 Uiso 1 1 calc R . . H8C H 0.0585 0.0495 0.3302 0.039 Uiso 1 1 calc R . . C7 C 0.2092(5) 0.0962(3) 0.08892(13) 0.0354(9) Uani 1 1 d . . . H7A H 0.1767 0.1622 0.0891 0.053 Uiso 1 1 calc R . . H7B H 0.1850 0.0696 0.0571 0.053 Uiso 1 1 calc R . . H7C H 0.3092 0.0948 0.0982 0.053 Uiso 1 1 calc R . . C36 C 0.1364(8) 0.1413(4) 0.4446(2) 0.0723(17) Uani 1 1 d . . . H36 H 0.0528 0.1722 0.4266 0.087 Uiso 1 1 calc R . . C24 C 0.1190(4) 0.4702(3) 0.43557(13) 0.0332(8) Uani 1 1 d . . . H24A H 0.1433 0.5223 0.4157 0.050 Uiso 1 1 calc R . . H24B H 0.0557 0.4938 0.4561 0.050 Uiso 1 1 calc R . . H24C H 0.0747 0.4191 0.4155 0.050 Uiso 1 1 calc R . . C35 C 0.3278(6) 0.7387(3) 0.41531(16) 0.0489(11) Uani 1 1 d . . . H35 H 0.3585 0.7149 0.4481 0.059 Uiso 1 1 calc R A 1 C15 C 0.3001(10) 0.5759(5) 0.06793(18) 0.097(3) Uani 1 1 d . . . H15A H 0.3939 0.5777 0.0853 0.146 Uiso 1 1 calc R . . H15B H 0.2996 0.6009 0.0360 0.146 Uiso 1 1 calc R . . H15C H 0.2668 0.5101 0.0661 0.146 Uiso 1 1 calc R . . Cl1 Cl 0.36939(13) 0.65515(9) 0.37429(4) 0.0494(3) Uani 1 1 d . A . Cl6 Cl 0.1059(2) 0.01664(11) 0.44569(6) 0.0793(5) Uani 1 1 d . . . Cl5 Cl 0.1594(3) 0.18550(16) 0.50283(7) 0.1198(10) Uani 1 1 d . . . Cl4 Cl 0.2715(4) 0.16456(18) 0.41572(9) 0.1324(11) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl2 0.084(2) 0.0435(13) 0.108(3) 0.0148(13) -0.0010(16) -0.0073(11) Cl3 0.0405(11) 0.0598(13) 0.0401(11) 0.0189(9) 0.0168(8) 0.0227(11) Cl2B 0.53(3) 0.064(6) 0.197(12) 0.043(6) -0.234(19) -0.102(11) Cl3B 0.208(13) 0.287(17) 0.067(5) 0.054(7) 0.044(7) 0.218(13) O5 0.0226(11) 0.0143(10) 0.0153(10) 0.0013(8) 0.0021(8) 0.0020(8) O2 0.0327(12) 0.0215(11) 0.0146(11) -0.0039(9) 0.0070(9) -0.0096(9) O1 0.0308(12) 0.0130(10) 0.0196(11) -0.0007(8) 0.0061(9) -0.0064(9) O3 0.0349(13) 0.0147(10) 0.0183(11) 0.0016(8) 0.0091(9) -0.0055(9) O4 0.0548(16) 0.0168(11) 0.0148(11) 0.0024(9) -0.0004(11) 0.0089(11) O9 0.0276(13) 0.0543(17) 0.0179(12) -0.0020(11) 0.0087(10) 0.0062(12) O8 0.0296(14) 0.077(2) 0.0160(12) 0.0024(13) -0.0021(10) 0.0152(14) O7 0.0391(15) 0.0628(19) 0.0127(12) 0.0004(12) 0.0048(10) 0.0102(14) O6 0.090(2) 0.0313(14) 0.0125(12) 0.0040(10) 0.0130(13) 0.0208(15) C16 0.0210(14) 0.0156(14) 0.0139(14) 0.0017(11) 0.0035(11) 0.0011(11) C5 0.0200(14) 0.0129(13) 0.0162(14) 0.0001(11) 0.0023(11) 0.0040(11) C1 0.0170(13) 0.0113(13) 0.0219(15) -0.0023(11) 0.0050(11) 0.0012(11) C21 0.0211(15) 0.0210(15) 0.0157(14) 0.0010(12) 0.0013(11) -0.0011(12) C25 0.0166(13) 0.0116(13) 0.0151(14) -0.0007(10) 0.0025(11) -0.0001(10) C28 0.0191(14) 0.0129(13) 0.0134(13) -0.0012(10) 0.0024(11) -0.0007(11) C27 0.0184(14) 0.0125(13) 0.0149(14) 0.0002(11) 0.0049(11) -0.0004(11) C26 0.0153(13) 0.0123(13) 0.0147(13) 0.0006(10) 0.0027(10) -0.0008(10) C6 0.0187(14) 0.0119(13) 0.0199(15) 0.0039(11) 0.0050(11) 0.0030(11) C4 0.0154(13) 0.0117(13) 0.0172(14) -0.0008(11) 0.0022(11) 0.0036(10) C9 0.0337(17) 0.0133(14) 0.0144(14) 0.0010(11) -0.0010(12) 0.0002(12) C30 0.0163(13) 0.0135(13) 0.0152(14) 0.0008(11) 0.0026(11) 0.0004(11) C3 0.0209(14) 0.0138(14) 0.0154(14) 0.0014(11) 0.0046(11) 0.0000(11) C10 0.0183(14) 0.0118(13) 0.0172(14) -0.0011(11) 0.0032(11) -0.0035(11) C2 0.0213(14) 0.0148(14) 0.0150(14) -0.0014(11) 0.0040(11) 0.0016(11) C19 0.0216(15) 0.0249(16) 0.0162(15) -0.0013(12) 0.0027(12) 0.0026(12) C29 0.0159(13) 0.0138(13) 0.0146(14) 0.0000(11) 0.0015(11) 0.0006(11) C20 0.0217(15) 0.0144(13) 0.0149(14) -0.0005(11) 0.0027(11) -0.0025(11) C11 0.0183(13) 0.0148(13) 0.0118(13) 0.0001(11) 0.0022(10) -0.0035(11) C13 0.0398(19) 0.0166(15) 0.0168(15) -0.0018(12) 0.0070(13) 0.0035(13) C12 0.0223(15) 0.0121(13) 0.0162(14) 0.0002(11) 0.0026(11) -0.0039(11) C31 0.0188(14) 0.0169(14) 0.0179(14) -0.0011(11) 0.0048(11) 0.0038(11) C32 0.0197(14) 0.0185(14) 0.0164(14) -0.0003(11) 0.0057(11) -0.0031(11) C14 0.048(2) 0.0203(16) 0.0118(15) 0.0006(12) 0.0049(14) 0.0030(15) C33 0.0136(13) 0.0217(15) 0.0186(15) -0.0013(12) 0.0009(11) -0.0006(11) C34 0.0155(14) 0.0222(15) 0.0181(15) -0.0010(12) 0.0054(11) 0.0007(11) C18 0.0269(17) 0.0352(19) 0.0154(15) 0.0009(13) -0.0013(13) 0.0055(14) C23 0.0253(16) 0.0314(18) 0.0233(17) -0.0034(14) -0.0037(13) 0.0025(14) C22 0.0263(16) 0.0264(16) 0.0188(15) 0.0000(13) 0.0078(13) 0.0005(13) C17 0.0323(18) 0.0351(18) 0.0125(15) 0.0007(13) 0.0038(13) 0.0022(15) C8 0.043(2) 0.0198(16) 0.0170(16) 0.0025(12) 0.0089(14) -0.0029(14) C7 0.053(2) 0.037(2) 0.0194(17) -0.0052(15) 0.0147(16) -0.0218(18) C36 0.090(5) 0.061(4) 0.061(4) -0.006(3) -0.005(3) 0.007(3) C24 0.0253(17) 0.050(2) 0.0264(18) -0.0037(16) 0.0092(14) 0.0066(16) C35 0.072(3) 0.042(2) 0.032(2) 0.0030(18) 0.007(2) 0.014(2) C15 0.199(8) 0.076(4) 0.027(2) 0.018(3) 0.048(4) 0.080(5) Cl1 0.0571(7) 0.0632(7) 0.0266(5) -0.0025(5) 0.0022(4) 0.0182(5) Cl6 0.1289(15) 0.0539(8) 0.0561(8) 0.0037(6) 0.0176(9) -0.0088(8) Cl5 0.183(2) 0.0885(14) 0.0728(12) -0.0337(10) -0.0280(13) 0.0419(15) Cl4 0.213(3) 0.0890(14) 0.1006(16) -0.0049(12) 0.0400(18) -0.0669(18) _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 Cl2 C35 1.752(6) . ? Cl3 C35 1.837(6) . ? Cl2B C35 1.822(18) . ? Cl3B C35 1.464(17) . ? O5 C10 1.381(4) . ? O5 C16 1.434(3) . ? O2 C2 1.372(4) . ? O2 C7 1.427(4) . ? O1 C1 1.382(4) . ? O1 H1 0.8400 . ? O3 C6 1.372(4) . ? O3 C8 1.429(4) . ? O4 C9 1.371(4) . ? O4 H4 0.8400 . ? O9 C22 1.380(4) . ? O9 C24 1.423(5) . ? O8 C18 1.376(4) . ? O8 C23 1.412(4) . ? O7 C17 1.376(4) . ? O7 H7 0.8400 . ? O6 C14 1.374(4) . ? O6 C15 1.427(6) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C5 C4 1.388(4) . ? C5 C6 1.392(4) . ? C5 H5 0.9500 . ? C1 C6 1.384(4) . ? C1 C2 1.398(4) . ? C21 C22 1.386(4) . ? C21 C20 1.399(4) . ? C21 H21 0.9500 . ? C25 C4 1.534(4) . ? C25 C30 1.540(4) . ? C25 C31 1.544(4) . ? C25 C26 1.551(4) . ? C28 C27 1.544(4) . ? C28 C29 1.544(4) . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C27 C12 1.529(4) . ? C27 C32 1.544(4) . ? C27 C26 1.552(4) . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C4 C3 1.406(4) . ? C9 C10 1.393(4) . ? C9 C14 1.397(5) . ? C30 C29 1.551(4) . ? C30 H30A 0.9900 . ? C30 H30B 0.9900 . ? C3 C2 1.391(4) . ? C3 H3 0.9500 . ? C10 C11 1.397(4) . ? C19 C20 1.397(4) . ? C19 C18 1.399(4) . ? C19 H19 0.9500 . ? C29 C33 1.531(4) . ? C29 C20 1.534(4) . ? C11 C12 1.391(4) . ? C11 H11 0.9500 . ? C13 C14 1.387(5) . ? C13 C12 1.400(4) . ? C13 H13 0.9500 . ? C31 C34 1.536(4) . ? C31 H31A 0.9900 . ? C31 H31B 0.9900 . ? C32 C34 1.532(4) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C33 C34 1.531(4) . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? C34 H34 1.0000 . ? C18 C17 1.384(5) . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C22 C17 1.390(5) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C36 Cl4 1.706(8) . ? C36 Cl5 1.764(6) . ? C36 Cl6 1.777(7) . ? C36 H36 1.0000 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C35 Cl1 1.755(5) . ? C35 H35 1.0000 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C10 O5 C16 116.0(2) . . ? C2 O2 C7 116.5(2) . . ? C1 O1 H1 109.5 . . ? C6 O3 C8 117.5(2) . . ? C9 O4 H4 109.5 . . ? C22 O9 C24 116.2(3) . . ? C18 O8 C23 117.6(3) . . ? C17 O7 H7 109.5 . . ? C14 O6 C15 117.5(3) . . ? O5 C16 H16A 109.5 . . ? O5 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? O5 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C4 C5 C6 120.0(3) . . ? C4 C5 H5 120.0 . . ? C6 C5 H5 120.0 . . ? O1 C1 C6 120.5(3) . . ? O1 C1 C2 120.1(3) . . ? C6 C1 C2 119.4(3) . . ? C22 C21 C20 120.0(3) . . ? C22 C21 H21 120.0 . . ? C20 C21 H21 120.0 . . ? C4 C25 C30 111.9(2) . . ? C4 C25 C31 109.7(2) . . ? C30 C25 C31 108.6(2) . . ? C4 C25 C26 110.2(2) . . ? C30 C25 C26 107.8(2) . . ? C31 C25 C26 108.5(2) . . ? C27 C28 C29 111.8(2) . . ? C27 C28 H28A 109.3 . . ? C29 C28 H28A 109.3 . . ? C27 C28 H28B 109.3 . . ? C29 C28 H28B 109.3 . . ? H28A C28 H28B 107.9 . . ? C12 C27 C32 110.3(2) . . ? C12 C27 C28 112.7(2) . . ? C32 C27 C28 108.0(2) . . ? C12 C27 C26 109.0(2) . . ? C32 C27 C26 109.0(2) . . ? C28 C27 C26 107.9(2) . . ? C25 C26 C27 111.6(2) . . ? C25 C26 H26A 109.3 . . ? C27 C26 H26A 109.3 . . ? C25 C26 H26B 109.3 . . ? C27 C26 H26B 109.3 . . ? H26A C26 H26B 108.0 . . ? O3 C6 C1 113.2(3) . . ? O3 C6 C5 125.5(3) . . ? C1 C6 C5 121.3(3) . . ? C5 C4 C3 118.7(3) . . ? C5 C4 C25 122.4(3) . . ? C3 C4 C25 118.9(3) . . ? O4 C9 C10 123.4(3) . . ? O4 C9 C14 118.1(3) . . ? C10 C9 C14 118.4(3) . . ? C25 C30 C29 111.5(2) . . ? C25 C30 H30A 109.3 . . ? C29 C30 H30A 109.3 . . ? C25 C30 H30B 109.3 . . ? C29 C30 H30B 109.3 . . ? H30A C30 H30B 108.0 . . ? C2 C3 C4 121.2(3) . . ? C2 C3 H3 119.4 . . ? C4 C3 H3 119.4 . . ? O5 C10 C9 115.2(3) . . ? O5 C10 C11 124.1(3) . . ? C9 C10 C11 120.6(3) . . ? O2 C2 C3 124.9(3) . . ? O2 C2 C1 115.8(3) . . ? C3 C2 C1 119.4(3) . . ? C20 C19 C18 120.6(3) . . ? C20 C19 H19 119.7 . . ? C18 C19 H19 119.7 . . ? C33 C29 C20 111.9(2) . . ? C33 C29 C28 108.5(2) . . ? C20 C29 C28 111.1(2) . . ? C33 C29 C30 108.4(2) . . ? C20 C29 C30 108.4(2) . . ? C28 C29 C30 108.5(2) . . ? C19 C20 C21 119.0(3) . . ? C19 C20 C29 121.2(3) . . ? C21 C20 C29 119.8(3) . . ? C12 C11 C10 120.9(3) . . ? C12 C11 H11 119.6 . . ? C10 C11 H11 119.6 . . ? C14 C13 C12 120.8(3) . . ? C14 C13 H13 119.6 . . ? C12 C13 H13 119.6 . . ? C11 C12 C13 118.3(3) . . ? C11 C12 C27 122.2(3) . . ? C13 C12 C27 119.4(3) . . ? C34 C31 C25 110.4(2) . . ? C34 C31 H31A 109.6 . . ? C25 C31 H31A 109.6 . . ? C34 C31 H31B 109.6 . . ? C25 C31 H31B 109.6 . . ? H31A C31 H31B 108.1 . . ? C34 C32 C27 110.2(2) . . ? C34 C32 H32A 109.6 . . ? C27 C32 H32A 109.6 . . ? C34 C32 H32B 109.6 . . ? C27 C32 H32B 109.6 . . ? H32A C32 H32B 108.1 . . ? O6 C14 C13 124.4(3) . . ? O6 C14 C9 114.6(3) . . ? C13 C14 C9 120.9(3) . . ? C29 C33 C34 110.4(2) . . ? C29 C33 H33A 109.6 . . ? C34 C33 H33A 109.6 . . ? C29 C33 H33B 109.6 . . ? C34 C33 H33B 109.6 . . ? H33A C33 H33B 108.1 . . ? C33 C34 C32 110.3(2) . . ? C33 C34 C31 109.4(2) . . ? C32 C34 C31 109.5(2) . . ? C33 C34 H34 109.2 . . ? C32 C34 H34 109.2 . . ? C31 C34 H34 109.2 . . ? O8 C18 C17 115.0(3) . . ? O8 C18 C19 125.0(3) . . ? C17 C18 C19 120.0(3) . . ? O8 C23 H23A 109.5 . . ? O8 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? O8 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? O9 C22 C21 126.0(3) . . ? O9 C22 C17 112.9(3) . . ? C21 C22 C17 121.0(3) . . ? O7 C17 C18 119.3(3) . . ? O7 C17 C22 121.2(3) . . ? C18 C17 C22 119.5(3) . . ? O3 C8 H8A 109.5 . . ? O3 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? O3 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? O2 C7 H7A 109.5 . . ? O2 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? O2 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? Cl4 C36 Cl5 113.5(4) . . ? Cl4 C36 Cl6 110.2(4) . . ? Cl5 C36 Cl6 109.1(4) . . ? Cl4 C36 H36 108.0 . . ? Cl5 C36 H36 108.0 . . ? Cl6 C36 H36 108.0 . . ? O9 C24 H24A 109.5 . . ? O9 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? O9 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? Cl3B C35 Cl2 101.5(9) . . ? Cl3B C35 Cl1 114.1(8) . . ? Cl2 C35 Cl1 109.1(3) . . ? Cl3B C35 Cl2B 120.5(11) . . ? Cl2 C35 Cl2B 21.3(5) . . ? Cl1 C35 Cl2B 105.8(9) . . ? Cl3B C35 Cl3 6.3(9) . . ? Cl2 C35 Cl3 107.8(3) . . ? Cl1 C35 Cl3 110.3(3) . . ? Cl2B C35 Cl3 126.9(9) . . ? Cl3B C35 H35 112.0 . . ? Cl2 C35 H35 109.9 . . ? Cl1 C35 H35 109.9 . . ? Cl2B C35 H35 92.3 . . ? Cl3 C35 H35 109.9 . . ? O6 C15 H15A 109.5 . . ? O6 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? O6 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C29 C28 C27 C12 178.9(2) . . . . ? C29 C28 C27 C32 -59.1(3) . . . . ? C29 C28 C27 C26 58.6(3) . . . . ? C4 C25 C26 C27 -177.8(2) . . . . ? C30 C25 C26 C27 59.9(3) . . . . ? C31 C25 C26 C27 -57.6(3) . . . . ? C12 C27 C26 C25 178.0(2) . . . . ? C32 C27 C26 C25 57.7(3) . . . . ? C28 C27 C26 C25 -59.4(3) . . . . ? C8 O3 C6 C1 179.1(3) . . . . ? C8 O3 C6 C5 -0.8(4) . . . . ? O1 C1 C6 O3 0.9(4) . . . . ? C2 C1 C6 O3 -178.5(3) . . . . ? O1 C1 C6 C5 -179.3(3) . . . . ? C2 C1 C6 C5 1.3(4) . . . . ? C4 C5 C6 O3 178.9(3) . . . . ? C4 C5 C6 C1 -0.8(4) . . . . ? C6 C5 C4 C3 0.1(4) . . . . ? C6 C5 C4 C25 -179.0(3) . . . . ? C30 C25 C4 C5 0.5(4) . . . . ? C31 C25 C4 C5 121.1(3) . . . . ? C26 C25 C4 C5 -119.5(3) . . . . ? C30 C25 C4 C3 -178.6(2) . . . . ? C31 C25 C4 C3 -58.0(3) . . . . ? C26 C25 C4 C3 61.4(3) . . . . ? C4 C25 C30 C29 179.4(2) . . . . ? C31 C25 C30 C29 58.1(3) . . . . ? C26 C25 C30 C29 -59.3(3) . . . . ? C5 C4 C3 C2 0.3(4) . . . . ? C25 C4 C3 C2 179.4(3) . . . . ? C16 O5 C10 C9 -176.1(3) . . . . ? C16 O5 C10 C11 2.5(4) . . . . ? O4 C9 C10 O5 -0.1(5) . . . . ? C14 C9 C10 O5 179.7(3) . . . . ? O4 C9 C10 C11 -178.8(3) . . . . ? C14 C9 C10 C11 1.1(5) . . . . ? C7 O2 C2 C3 3.3(5) . . . . ? C7 O2 C2 C1 -175.8(3) . . . . ? C4 C3 C2 O2 -178.9(3) . . . . ? C4 C3 C2 C1 0.2(4) . . . . ? O1 C1 C2 O2 -1.2(4) . . . . ? C6 C1 C2 O2 178.2(3) . . . . ? O1 C1 C2 C3 179.6(3) . . . . ? C6 C1 C2 C3 -0.9(4) . . . . ? C27 C28 C29 C33 59.1(3) . . . . ? C27 C28 C29 C20 -177.5(2) . . . . ? C27 C28 C29 C30 -58.5(3) . . . . ? C25 C30 C29 C33 -58.8(3) . . . . ? C25 C30 C29 C20 179.6(2) . . . . ? C25 C30 C29 C28 58.8(3) . . . . ? C18 C19 C20 C21 0.8(5) . . . . ? C18 C19 C20 C29 -176.0(3) . . . . ? C22 C21 C20 C19 0.0(5) . . . . ? C22 C21 C20 C29 176.9(3) . . . . ? C33 C29 C20 C19 -13.5(4) . . . . ? C28 C29 C20 C19 -134.9(3) . . . . ? C30 C29 C20 C19 106.0(3) . . . . ? C33 C29 C20 C21 169.6(3) . . . . ? C28 C29 C20 C21 48.3(4) . . . . ? C30 C29 C20 C21 -70.9(3) . . . . ? O5 C10 C11 C12 -179.4(3) . . . . ? C9 C10 C11 C12 -0.9(4) . . . . ? C10 C11 C12 C13 -0.6(4) . . . . ? C10 C11 C12 C27 -179.6(3) . . . . ? C14 C13 C12 C11 1.9(5) . . . . ? C14 C13 C12 C27 -179.0(3) . . . . ? C32 C27 C12 C11 -132.4(3) . . . . ? C28 C27 C12 C11 -11.7(4) . . . . ? C26 C27 C12 C11 108.0(3) . . . . ? C32 C27 C12 C13 48.6(4) . . . . ? C28 C27 C12 C13 169.3(3) . . . . ? C26 C27 C12 C13 -71.0(3) . . . . ? C4 C25 C31 C34 179.2(2) . . . . ? C30 C25 C31 C34 -58.2(3) . . . . ? C26 C25 C31 C34 58.7(3) . . . . ? C12 C27 C32 C34 -178.1(2) . . . . ? C28 C27 C32 C34 58.4(3) . . . . ? C26 C27 C32 C34 -58.5(3) . . . . ? C15 O6 C14 C13 -11.5(7) . . . . ? C15 O6 C14 C9 168.6(5) . . . . ? C12 C13 C14 O6 178.4(3) . . . . ? C12 C13 C14 C9 -1.7(6) . . . . ? O4 C9 C14 O6 -0.1(5) . . . . ? C10 C9 C14 O6 -179.9(3) . . . . ? O4 C9 C14 C13 -179.9(3) . . . . ? C10 C9 C14 C13 0.2(5) . . . . ? C20 C29 C33 C34 178.9(2) . . . . ? C28 C29 C33 C34 -58.2(3) . . . . ? C30 C29 C33 C34 59.4(3) . . . . ? C29 C33 C34 C32 59.7(3) . . . . ? C29 C33 C34 C31 -60.8(3) . . . . ? C27 C32 C34 C33 -59.8(3) . . . . ? C27 C32 C34 C31 60.6(3) . . . . ? C25 C31 C34 C33 60.0(3) . . . . ? C25 C31 C34 C32 -61.0(3) . . . . ? C23 O8 C18 C17 -166.5(3) . . . . ? C23 O8 C18 C19 12.7(6) . . . . ? C20 C19 C18 O8 179.9(3) . . . . ? C20 C19 C18 C17 -1.0(5) . . . . ? C24 O9 C22 C21 -7.7(5) . . . . ? C24 O9 C22 C17 171.8(3) . . . . ? C20 C21 C22 O9 178.7(3) . . . . ? C20 C21 C22 C17 -0.7(5) . . . . ? O8 C18 C17 O7 -0.2(5) . . . . ? C19 C18 C17 O7 -179.4(3) . . . . ? O8 C18 C17 C22 179.5(3) . . . . ? C19 C18 C17 C22 0.3(6) . . . . ? O9 C22 C17 O7 0.8(5) . . . . ? C21 C22 C17 O7 -179.7(3) . . . . ? O9 C22 C17 C18 -178.9(3) . . . . ? C21 C22 C17 C18 0.6(5) . . . . ? 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 O1 H1 O5 0.84 2.29 2.919(3) 131.9 1_545 O4 H4 O1 0.84 2.01 2.836(3) 167.5 1_565 _diffrn_measured_fraction_theta_max 0.906 _diffrn_reflns_theta_full 27.20 _diffrn_measured_fraction_theta_full 0.906 _refine_diff_density_max 1.793 _refine_diff_density_min -1.510 _refine_diff_density_rms 0.113 # Attachment '740185.cif' data_a0906191kka _database_code_depnum_ccdc_archive 'CCDC 740185' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C40 H43 N3 O15' _chemical_formula_weight 805.77 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1)/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.0663(11) _cell_length_b 19.591(2) _cell_length_c 19.371(2) _cell_angle_alpha 90.00 _cell_angle_beta 98.6230(10) _cell_angle_gamma 90.00 _cell_volume 3777.0(7) _cell_formula_units_Z 4 _cell_measurement_temperature 120 _cell_measurement_reflns_used 4450 _cell_measurement_theta_min 2.34 _cell_measurement_theta_max 26.91 _exptl_crystal_description prismatic _exptl_crystal_colour red _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.417 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1696 _exptl_absorpt_coefficient_mu 0.109 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9784 _exptl_absorpt_correction_T_max 0.9891 _exptl_absorpt_process_details ; SADABS Sheldrick 1996 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 120 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEXII CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.333 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18129 _diffrn_reflns_av_R_equivalents 0.0275 _diffrn_reflns_av_sigmaI/netI 0.0415 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.49 _diffrn_reflns_theta_max 27.21 _reflns_number_total 7566 _reflns_number_gt 5119 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2006)' _computing_cell_refinement 'APEX2 (Bruker AXS, 2006)' _computing_data_reduction 'SAINT (Bruker AXS, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XSHEL (Bruker AXS,2002)' _computing_publication_material 'XCIF (Bruker AXS, 2001)' _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^)+(0.0419P)^2^+1.2814P] 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 7566 _refine_ls_number_parameters 532 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0733 _refine_ls_R_factor_gt 0.0403 _refine_ls_wR_factor_ref 0.1010 _refine_ls_wR_factor_gt 0.0874 _refine_ls_goodness_of_fit_ref 1.008 _refine_ls_restrained_S_all 1.008 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O3 O 0.19222(11) 0.55862(6) 0.37407(7) 0.0221(3) Uani 1 1 d . . . O2 O 0.59742(11) 0.67637(6) 0.42482(7) 0.0215(3) Uani 1 1 d . . . O1 O 0.46051(11) 0.56039(6) 0.41456(7) 0.0214(3) Uani 1 1 d . . . H1 H 0.4061 0.5278 0.4144 0.032 Uiso 1 1 calc R . . O4 O -0.18046(12) 0.90362(7) -0.01395(7) 0.0273(3) Uani 1 1 d . . . H4 H -0.2634 0.9116 -0.0210 0.041 Uiso 1 1 calc R . . O7 O 0.53401(12) 1.17228(6) 0.42710(7) 0.0246(3) Uani 1 1 d . . . H7 H 0.4891 1.2084 0.4195 0.037 Uiso 1 1 calc R . . O5 O 0.07020(12) 0.86275(7) 0.02671(7) 0.0271(3) Uani 1 1 d . . . O8 O 0.27414(12) 1.19296(6) 0.38836(7) 0.0243(3) Uani 1 1 d . . . O9 O 0.64055(11) 1.04803(6) 0.43196(6) 0.0206(3) Uani 1 1 d . . . O6 O -0.35169(11) 0.92661(7) 0.08203(7) 0.0266(3) Uani 1 1 d . . . O14 O 0.18885(14) 0.69877(8) 0.16950(9) 0.0434(4) Uani 1 1 d . . . O15 O 0.13035(14) 0.59362(8) 0.18259(9) 0.0432(4) Uani 1 1 d . . . O12 O 0.79333(14) 0.69324(9) 0.28974(8) 0.0487(4) Uani 1 1 d . . . O11 O 0.65278(14) 0.45884(9) 0.31888(8) 0.0475(4) Uani 1 1 d . . . O13 O 0.64004(16) 0.77002(9) 0.25940(9) 0.0521(5) Uani 1 1 d . . . O10 O 0.47253(16) 0.42566(8) 0.25092(9) 0.0435(4) Uani 1 1 d . . . N3 N 0.21324(15) 0.63985(9) 0.18841(9) 0.0300(4) Uani 1 1 d . . . N1 N 0.54861(17) 0.47012(10) 0.27895(10) 0.0346(4) Uani 1 1 d . . . N2 N 0.67691(17) 0.71099(11) 0.26964(9) 0.0375(5) Uani 1 1 d . . . C1 C 0.39085(16) 0.62014(9) 0.40093(9) 0.0169(4) Uani 1 1 d . . . C27 C 0.02054(16) 0.88156(9) 0.27659(9) 0.0152(4) Uani 1 1 d . . . C19 C 0.22808(16) 1.06965(9) 0.37909(9) 0.0170(4) Uani 1 1 d . . . H19 H 0.1343 1.0764 0.3657 0.020 Uiso 1 1 calc R . . C2 C 0.45975(16) 0.68160(9) 0.40783(9) 0.0174(4) Uani 1 1 d . . . C28 C 0.11520(16) 0.94339(9) 0.29375(9) 0.0155(4) Uani 1 1 d . . . H28A H 0.1834 0.9434 0.2619 0.019 Uiso 1 1 calc R . . H28B H 0.0625 0.9861 0.2858 0.019 Uiso 1 1 calc R . . C10 C -0.00475(17) 0.87673(9) 0.07845(9) 0.0194(4) Uani 1 1 d . . . C20 C 0.28022(16) 1.00341(9) 0.38440(9) 0.0150(4) Uani 1 1 d . . . C34 C -0.01599(16) 0.88069(9) 0.40256(9) 0.0179(4) Uani 1 1 d . . . H34 H -0.0862 0.8821 0.4340 0.022 Uiso 1 1 calc R . . C5 C 0.18387(17) 0.68297(9) 0.36813(9) 0.0174(4) Uani 1 1 d . . . H5 H 0.0896 0.6829 0.3531 0.021 Uiso 1 1 calc R . . C33 C 0.07837(16) 0.94220(9) 0.41866(9) 0.0170(4) Uani 1 1 d . . . H33A H 0.1221 0.9402 0.4679 0.020 Uiso 1 1 calc R . . H33B H 0.0259 0.9850 0.4119 0.020 Uiso 1 1 calc R . . C3 C 0.39179(16) 0.74331(9) 0.39718(9) 0.0183(4) Uani 1 1 d . . . H3 H 0.4406 0.7849 0.4031 0.022 Uiso 1 1 calc R . . C26 C 0.10223(16) 0.81516(9) 0.29114(9) 0.0164(4) Uani 1 1 d . . . H26A H 0.0414 0.7755 0.2814 0.020 Uiso 1 1 calc R . . H26B H 0.1703 0.8126 0.2593 0.020 Uiso 1 1 calc R . . C11 C 0.04259(16) 0.87282(9) 0.14889(9) 0.0176(4) Uani 1 1 d . . . H11 H 0.1345 0.8620 0.1635 0.021 Uiso 1 1 calc R . . C13 C -0.17492(16) 0.89971(9) 0.17706(10) 0.0179(4) Uani 1 1 d . . . H13 H -0.2351 0.9057 0.2099 0.021 Uiso 1 1 calc R . . C6 C 0.25168(17) 0.62160(9) 0.38005(9) 0.0170(4) Uani 1 1 d . . . C21 C 0.41879(16) 0.99526(9) 0.40268(9) 0.0167(4) Uani 1 1 d . . . H21 H 0.4562 0.9506 0.4060 0.020 Uiso 1 1 calc R . . C12 C -0.04054(16) 0.88437(8) 0.19973(9) 0.0155(4) Uani 1 1 d . . . C9 C -0.13849(17) 0.89593(9) 0.05609(10) 0.0195(4) Uani 1 1 d . . . C17 C 0.45049(16) 1.11677(9) 0.41297(9) 0.0172(4) Uani 1 1 d . . . C4 C 0.25251(16) 0.74478(9) 0.37787(9) 0.0158(4) Uani 1 1 d . . . C25 C 0.17301(16) 0.81138(9) 0.36715(9) 0.0160(4) Uani 1 1 d . . . C31 C 0.06494(16) 0.81464(9) 0.41592(9) 0.0179(4) Uani 1 1 d . . . H31A H 0.0042 0.7748 0.4073 0.021 Uiso 1 1 calc R . . H31B H 0.1086 0.8131 0.4652 0.021 Uiso 1 1 calc R . . C18 C 0.31246(17) 1.12581(9) 0.39333(9) 0.0181(4) Uani 1 1 d . . . C30 C 0.26437(16) 0.87404(9) 0.38128(9) 0.0162(4) Uani 1 1 d . . . H30A H 0.3336 0.8726 0.3500 0.019 Uiso 1 1 calc R . . H30B H 0.3110 0.8722 0.4300 0.019 Uiso 1 1 calc R . . C22 C 0.50271(16) 1.05137(9) 0.41610(9) 0.0170(4) Uani 1 1 d . . . C29 C 0.18657(16) 0.94167(9) 0.36988(9) 0.0152(4) Uani 1 1 d . . . C36 C 0.61180(19) 0.59092(11) 0.27535(10) 0.0281(5) Uani 1 1 d . . . H36 H 0.7015 0.5798 0.2948 0.034 Uiso 1 1 calc R . . C40 C 0.38205(18) 0.55624(10) 0.23586(10) 0.0231(4) Uani 1 1 d . . . H40 H 0.3156 0.5215 0.2284 0.028 Uiso 1 1 calc R . . C14 C -0.22048(16) 0.90618(9) 0.10598(10) 0.0193(4) Uani 1 1 d . . . C32 C -0.08467(16) 0.88387(9) 0.32644(9) 0.0175(4) Uani 1 1 d . . . H32A H -0.1375 0.9265 0.3187 0.021 Uiso 1 1 calc R . . H32B H -0.1472 0.8449 0.3166 0.021 Uiso 1 1 calc R . . C39 C 0.35147(17) 0.62345(10) 0.21995(10) 0.0231(4) Uani 1 1 d . . . C8 C 0.04740(16) 0.55767(10) 0.36358(10) 0.0236(4) Uani 1 1 d . . . H8A H 0.0148 0.5828 0.4014 0.035 Uiso 1 1 calc R . . H8B H 0.0158 0.5103 0.3634 0.035 Uiso 1 1 calc R . . H8C H 0.0132 0.5792 0.3188 0.035 Uiso 1 1 calc R . . C38 C 0.44492(18) 0.67537(10) 0.23050(10) 0.0254(4) Uani 1 1 d . . . H38 H 0.4213 0.7214 0.2193 0.030 Uiso 1 1 calc R . . C24 C 0.69944(17) 0.98157(10) 0.43197(10) 0.0229(4) Uani 1 1 d . . . H24A H 0.6724 0.9544 0.4700 0.034 Uiso 1 1 calc R . . H24B H 0.7975 0.9857 0.4387 0.034 Uiso 1 1 calc R . . H24C H 0.6688 0.9591 0.3872 0.034 Uiso 1 1 calc R . . C23 C 0.13285(18) 1.20689(10) 0.37450(11) 0.0289(5) Uani 1 1 d . . . H23A H 0.0947 1.1862 0.3298 0.043 Uiso 1 1 calc R . . H23B H 0.1184 1.2564 0.3722 0.043 Uiso 1 1 calc R . . H23C H 0.0889 1.1876 0.4119 0.043 Uiso 1 1 calc R . . C37 C 0.57415(18) 0.65716(11) 0.25805(10) 0.0262(5) Uani 1 1 d . . . C35 C 0.51336(18) 0.54160(10) 0.26305(10) 0.0254(4) Uani 1 1 d . . . C16 C -0.44940(18) 0.87376(11) 0.08498(11) 0.0317(5) Uani 1 1 d . . . H16A H -0.4243 0.8334 0.0600 0.048 Uiso 1 1 calc R . . H16B H -0.5379 0.8900 0.0631 0.048 Uiso 1 1 calc R . . H16C H -0.4528 0.8618 0.1338 0.048 Uiso 1 1 calc R . . C7 C 0.67172(17) 0.73803(10) 0.44084(11) 0.0267(5) Uani 1 1 d . . . H7A H 0.6589 0.7682 0.4000 0.040 Uiso 1 1 calc R . . H7B H 0.7674 0.7272 0.4532 0.040 Uiso 1 1 calc R . . H7C H 0.6398 0.7609 0.4802 0.040 Uiso 1 1 calc R . . C15 C 0.20203(19) 0.83675(14) 0.04946(11) 0.0409(6) Uani 1 1 d . . . H15A H 0.2559 0.8715 0.0772 0.061 Uiso 1 1 calc R . . H15B H 0.2445 0.8250 0.0087 0.061 Uiso 1 1 calc R . . H15C H 0.1961 0.7959 0.0781 0.061 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O3 0.0180(6) 0.0140(7) 0.0335(8) -0.0002(6) 0.0010(6) -0.0003(5) O2 0.0142(6) 0.0194(7) 0.0295(8) -0.0010(6) -0.0008(5) 0.0000(5) O1 0.0204(6) 0.0132(7) 0.0302(8) 0.0020(6) 0.0029(6) 0.0027(5) O4 0.0215(7) 0.0363(9) 0.0218(8) 0.0023(6) -0.0043(6) -0.0055(6) O7 0.0241(7) 0.0171(7) 0.0321(8) -0.0027(6) 0.0025(6) -0.0052(5) O5 0.0203(6) 0.0418(9) 0.0193(7) -0.0018(6) 0.0029(5) -0.0008(6) O8 0.0210(6) 0.0136(7) 0.0369(8) -0.0013(6) -0.0001(6) 0.0010(5) O9 0.0128(6) 0.0218(7) 0.0268(8) -0.0020(6) 0.0013(5) 0.0004(5) O6 0.0158(6) 0.0255(8) 0.0352(8) -0.0009(6) -0.0066(6) 0.0001(5) O14 0.0329(8) 0.0333(10) 0.0617(11) 0.0095(8) -0.0004(7) 0.0080(7) O15 0.0241(7) 0.0387(10) 0.0639(12) 0.0032(8) -0.0027(7) -0.0048(7) O12 0.0256(8) 0.0697(13) 0.0495(11) -0.0085(9) 0.0012(7) -0.0134(8) O11 0.0316(8) 0.0612(12) 0.0523(11) 0.0274(9) 0.0150(8) 0.0216(8) O13 0.0496(10) 0.0374(11) 0.0681(13) -0.0068(9) 0.0045(9) -0.0153(8) O10 0.0508(10) 0.0292(9) 0.0549(11) 0.0087(8) 0.0222(8) 0.0022(8) N3 0.0222(8) 0.0338(11) 0.0337(11) -0.0003(8) 0.0032(7) 0.0029(8) N1 0.0307(10) 0.0395(12) 0.0380(11) 0.0139(9) 0.0190(9) 0.0116(9) N2 0.0297(10) 0.0501(14) 0.0331(11) -0.0085(9) 0.0057(8) -0.0137(9) C1 0.0193(8) 0.0160(10) 0.0157(10) 0.0002(7) 0.0033(7) 0.0029(7) C27 0.0144(8) 0.0134(9) 0.0181(9) 0.0003(7) 0.0031(7) -0.0001(7) C19 0.0146(8) 0.0173(10) 0.0190(10) -0.0008(7) 0.0024(7) 0.0005(7) C2 0.0169(8) 0.0199(10) 0.0154(10) 0.0007(7) 0.0022(7) 0.0013(7) C28 0.0135(8) 0.0128(9) 0.0200(10) 0.0000(7) 0.0020(7) 0.0003(7) C10 0.0198(9) 0.0177(10) 0.0208(10) -0.0020(8) 0.0036(8) -0.0050(7) C20 0.0181(8) 0.0150(9) 0.0122(9) -0.0012(7) 0.0032(7) 0.0000(7) C34 0.0155(8) 0.0185(10) 0.0209(10) -0.0004(8) 0.0067(7) 0.0007(7) C5 0.0158(8) 0.0172(10) 0.0186(10) 0.0001(7) 0.0009(7) 0.0000(7) C33 0.0163(8) 0.0158(9) 0.0190(10) -0.0025(7) 0.0033(7) 0.0010(7) C3 0.0188(9) 0.0173(10) 0.0190(10) -0.0008(7) 0.0032(7) -0.0013(7) C26 0.0161(8) 0.0127(9) 0.0203(10) -0.0009(7) 0.0030(7) -0.0011(7) C11 0.0136(8) 0.0184(10) 0.0203(10) 0.0001(8) 0.0008(7) -0.0021(7) C13 0.0164(8) 0.0134(9) 0.0241(11) -0.0019(7) 0.0036(8) -0.0020(7) C6 0.0201(9) 0.0144(9) 0.0166(10) -0.0009(7) 0.0030(7) -0.0018(7) C21 0.0180(9) 0.0153(9) 0.0168(10) -0.0002(7) 0.0022(7) 0.0014(7) C12 0.0162(8) 0.0099(9) 0.0201(10) -0.0014(7) 0.0014(7) -0.0022(7) C9 0.0216(9) 0.0168(10) 0.0183(10) 0.0017(7) -0.0025(8) -0.0054(7) C17 0.0197(9) 0.0165(10) 0.0153(10) -0.0020(7) 0.0029(7) -0.0050(7) C4 0.0187(8) 0.0152(9) 0.0137(9) 0.0012(7) 0.0031(7) 0.0006(7) C25 0.0149(8) 0.0138(9) 0.0192(10) -0.0005(7) 0.0017(7) 0.0000(7) C31 0.0198(9) 0.0152(9) 0.0192(10) 0.0004(7) 0.0045(7) -0.0022(7) C18 0.0210(9) 0.0147(10) 0.0187(10) 0.0000(7) 0.0035(7) 0.0031(7) C30 0.0154(8) 0.0150(9) 0.0181(10) 0.0000(7) 0.0021(7) 0.0013(7) C22 0.0143(8) 0.0218(10) 0.0152(10) -0.0002(8) 0.0029(7) 0.0002(7) C29 0.0143(8) 0.0145(9) 0.0169(10) -0.0012(7) 0.0024(7) 0.0006(7) C36 0.0207(9) 0.0441(14) 0.0199(11) 0.0001(9) 0.0039(8) 0.0017(9) C40 0.0233(9) 0.0261(11) 0.0213(11) -0.0013(8) 0.0083(8) -0.0014(8) C14 0.0136(8) 0.0154(10) 0.0273(11) 0.0000(8) -0.0026(8) -0.0026(7) C32 0.0153(8) 0.0146(9) 0.0231(10) -0.0007(8) 0.0043(7) 0.0007(7) C39 0.0199(9) 0.0308(12) 0.0191(10) -0.0028(8) 0.0046(8) 0.0015(8) C8 0.0177(9) 0.0178(10) 0.0344(12) -0.0024(8) 0.0010(8) -0.0017(8) C38 0.0284(10) 0.0277(11) 0.0207(11) -0.0043(8) 0.0060(8) -0.0005(8) C24 0.0156(9) 0.0241(11) 0.0288(11) -0.0057(8) 0.0024(8) 0.0044(8) C23 0.0229(9) 0.0180(11) 0.0449(14) -0.0001(9) 0.0023(9) 0.0073(8) C37 0.0241(10) 0.0336(12) 0.0216(11) -0.0046(9) 0.0055(8) -0.0055(9) C35 0.0269(10) 0.0305(12) 0.0209(11) 0.0047(9) 0.0100(8) 0.0069(9) C16 0.0178(9) 0.0434(14) 0.0341(13) -0.0085(10) 0.0047(9) -0.0073(9) C7 0.0200(9) 0.0233(11) 0.0350(12) -0.0003(9) -0.0016(8) -0.0041(8) C15 0.0209(10) 0.0776(19) 0.0247(12) -0.0059(11) 0.0050(9) 0.0039(11) _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 O3 C6 1.369(2) . ? O3 C8 1.442(2) . ? O2 C2 1.379(2) . ? O2 C7 1.430(2) . ? O1 C1 1.370(2) . ? O1 H1 0.8400 . ? O4 C9 1.367(2) . ? O4 H4 0.8400 . ? O7 C17 1.377(2) . ? O7 H7 0.8400 . ? O5 C10 1.370(2) . ? O5 C15 1.428(2) . ? O8 C18 1.370(2) . ? O8 C23 1.433(2) . ? O9 C22 1.3769(19) . ? O9 C24 1.431(2) . ? O6 C14 1.391(2) . ? O6 C16 1.435(2) . ? O14 N3 1.225(2) . ? O15 N3 1.225(2) . ? O12 N2 1.228(2) . ? O11 N1 1.226(2) . ? O13 N2 1.222(2) . ? O10 N1 1.231(2) . ? N3 C39 1.469(2) . ? N1 C35 1.466(3) . ? N2 C37 1.471(3) . ? C1 C2 1.386(2) . ? C1 C6 1.399(2) . ? C27 C12 1.524(2) . ? C27 C32 1.537(2) . ? C27 C26 1.542(2) . ? C27 C28 1.546(2) . ? C19 C18 1.392(2) . ? C19 C20 1.398(2) . ? C19 H19 0.9500 . ? C2 C3 1.389(2) . ? C28 C29 1.541(2) . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C10 C11 1.378(2) . ? C10 C9 1.402(2) . ? C20 C21 1.396(2) . ? C20 C29 1.533(2) . ? C34 C31 1.530(2) . ? C34 C32 1.533(2) . ? C34 C33 1.537(2) . ? C34 H34 1.0000 . ? C5 C6 1.385(2) . ? C5 C4 1.393(2) . ? C5 H5 0.9500 . ? C33 C29 1.545(2) . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? C3 C4 1.396(2) . ? C3 H3 0.9500 . ? C26 C25 1.538(2) . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C11 C12 1.403(2) . ? C11 H11 0.9500 . ? C13 C14 1.390(3) . ? C13 C12 1.391(2) . ? C13 H13 0.9500 . ? C21 C22 1.387(2) . ? C21 H21 0.9500 . ? C9 C14 1.376(3) . ? C17 C22 1.383(2) . ? C17 C18 1.396(2) . ? C4 C25 1.529(2) . ? C25 C30 1.534(2) . ? C25 C31 1.545(2) . ? C31 H31A 0.9900 . ? C31 H31B 0.9900 . ? C30 C29 1.538(2) . ? C30 H30A 0.9900 . ? C30 H30B 0.9900 . ? C36 C35 1.379(3) . ? C36 C37 1.379(3) . ? C36 H36 0.9500 . ? C40 C39 1.377(3) . ? C40 C35 1.378(3) . ? C40 H40 0.9500 . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C39 C38 1.380(3) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C38 C37 1.377(3) . ? C38 H38 0.9500 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 O3 C8 116.34(13) . . ? C2 O2 C7 117.59(13) . . ? C1 O1 H1 109.5 . . ? C9 O4 H4 109.5 . . ? C17 O7 H7 109.5 . . ? C10 O5 C15 115.71(15) . . ? C18 O8 C23 117.19(14) . . ? C22 O9 C24 116.55(13) . . ? C14 O6 C16 113.65(14) . . ? O14 N3 O15 124.47(16) . . ? O14 N3 C39 117.74(16) . . ? O15 N3 C39 117.79(17) . . ? O11 N1 O10 124.56(19) . . ? O11 N1 C35 117.51(19) . . ? O10 N1 C35 117.92(17) . . ? O13 N2 O12 124.86(19) . . ? O13 N2 C37 117.67(18) . . ? O12 N2 C37 117.5(2) . . ? O1 C1 C2 119.31(15) . . ? O1 C1 C6 122.32(16) . . ? C2 C1 C6 118.37(16) . . ? C12 C27 C32 113.42(13) . . ? C12 C27 C26 109.56(14) . . ? C32 C27 C26 107.99(14) . . ? C12 C27 C28 109.08(14) . . ? C32 C27 C28 107.60(14) . . ? C26 C27 C28 109.09(13) . . ? C18 C19 C20 120.53(15) . . ? C18 C19 H19 119.7 . . ? C20 C19 H19 119.7 . . ? O2 C2 C1 115.40(15) . . ? O2 C2 C3 123.70(16) . . ? C1 C2 C3 120.90(15) . . ? C29 C28 C27 111.87(14) . . ? C29 C28 H28A 109.2 . . ? C27 C28 H28A 109.2 . . ? C29 C28 H28B 109.2 . . ? C27 C28 H28B 109.2 . . ? H28A C28 H28B 107.9 . . ? O5 C10 C11 124.52(16) . . ? O5 C10 C9 115.86(16) . . ? C11 C10 C9 119.62(17) . . ? C21 C20 C19 118.33(16) . . ? C21 C20 C29 121.33(15) . . ? C19 C20 C29 120.34(15) . . ? C31 C34 C32 110.43(14) . . ? C31 C34 C33 109.36(14) . . ? C32 C34 C33 109.82(15) . . ? C31 C34 H34 109.1 . . ? C32 C34 H34 109.1 . . ? C33 C34 H34 109.1 . . ? C6 C5 C4 120.67(15) . . ? C6 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? C34 C33 C29 109.96(14) . . ? C34 C33 H33A 109.7 . . ? C29 C33 H33A 109.7 . . ? C34 C33 H33B 109.7 . . ? C29 C33 H33B 109.7 . . ? H33A C33 H33B 108.2 . . ? C2 C3 C4 120.67(16) . . ? C2 C3 H3 119.7 . . ? C4 C3 H3 119.7 . . ? C25 C26 C27 111.92(14) . . ? C25 C26 H26A 109.2 . . ? C27 C26 H26A 109.2 . . ? C25 C26 H26B 109.2 . . ? C27 C26 H26B 109.2 . . ? H26A C26 H26B 107.9 . . ? C10 C11 C12 122.13(16) . . ? C10 C11 H11 118.9 . . ? C12 C11 H11 118.9 . . ? C14 C13 C12 119.55(17) . . ? C14 C13 H13 120.2 . . ? C12 C13 H13 120.2 . . ? O3 C6 C5 124.76(15) . . ? O3 C6 C1 114.35(15) . . ? C5 C6 C1 120.87(16) . . ? C22 C21 C20 120.96(16) . . ? C22 C21 H21 119.5 . . ? C20 C21 H21 119.5 . . ? C13 C12 C11 117.86(16) . . ? C13 C12 C27 123.15(16) . . ? C11 C12 C27 118.96(14) . . ? O4 C9 C14 123.50(16) . . ? O4 C9 C10 118.39(16) . . ? C14 C9 C10 118.11(16) . . ? O7 C17 C22 120.42(15) . . ? O7 C17 C18 120.48(16) . . ? C22 C17 C18 119.07(16) . . ? C5 C4 C3 118.44(16) . . ? C5 C4 C25 118.99(14) . . ? C3 C4 C25 122.56(15) . . ? C4 C25 C30 111.80(13) . . ? C4 C25 C26 109.22(14) . . ? C30 C25 C26 108.16(14) . . ? C4 C25 C31 110.75(14) . . ? C30 C25 C31 108.42(14) . . ? C26 C25 C31 108.41(13) . . ? C34 C31 C25 109.70(14) . . ? C34 C31 H31A 109.7 . . ? C25 C31 H31A 109.7 . . ? C34 C31 H31B 109.7 . . ? C25 C31 H31B 109.7 . . ? H31A C31 H31B 108.2 . . ? O8 C18 C19 126.01(15) . . ? O8 C18 C17 113.53(15) . . ? C19 C18 C17 120.44(16) . . ? C25 C30 C29 112.65(13) . . ? C25 C30 H30A 109.1 . . ? C29 C30 H30A 109.1 . . ? C25 C30 H30B 109.1 . . ? C29 C30 H30B 109.1 . . ? H30A C30 H30B 107.8 . . ? O9 C22 C17 114.68(15) . . ? O9 C22 C21 124.70(16) . . ? C17 C22 C21 120.61(15) . . ? C20 C29 C30 111.55(13) . . ? C20 C29 C28 110.12(14) . . ? C30 C29 C28 108.09(14) . . ? C20 C29 C33 110.66(14) . . ? C30 C29 C33 107.96(14) . . ? C28 C29 C33 108.35(13) . . ? C35 C36 C37 116.94(18) . . ? C35 C36 H36 121.5 . . ? C37 C36 H36 121.5 . . ? C39 C40 C35 117.01(18) . . ? C39 C40 H40 121.5 . . ? C35 C40 H40 121.5 . . ? C9 C14 C13 122.58(16) . . ? C9 C14 O6 116.55(16) . . ? C13 C14 O6 120.80(16) . . ? C34 C32 C27 110.43(13) . . ? C34 C32 H32A 109.6 . . ? C27 C32 H32A 109.6 . . ? C34 C32 H32B 109.6 . . ? C27 C32 H32B 109.6 . . ? H32A C32 H32B 108.1 . . ? C40 C39 C38 123.19(17) . . ? C40 C39 N3 117.92(17) . . ? C38 C39 N3 118.86(18) . . ? O3 C8 H8A 109.5 . . ? O3 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? O3 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C37 C38 C39 116.73(19) . . ? C37 C38 H38 121.6 . . ? C39 C38 H38 121.6 . . ? O9 C24 H24A 109.5 . . ? O9 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? O9 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? O8 C23 H23A 109.5 . . ? O8 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? O8 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C38 C37 C36 123.18(18) . . ? C38 C37 N2 118.38(19) . . ? C36 C37 N2 118.44(18) . . ? C40 C35 C36 122.93(19) . . ? C40 C35 N1 117.86(18) . . ? C36 C35 N1 119.21(18) . . ? O6 C16 H16A 109.5 . . ? O6 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? O6 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? O2 C7 H7A 109.5 . . ? O2 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? O2 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? O5 C15 H15A 109.5 . . ? O5 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? O5 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C7 O2 C2 C1 -172.61(16) . . . . ? C7 O2 C2 C3 8.2(2) . . . . ? O1 C1 C2 O2 3.3(2) . . . . ? C6 C1 C2 O2 -176.58(15) . . . . ? O1 C1 C2 C3 -177.40(16) . . . . ? C6 C1 C2 C3 2.7(3) . . . . ? C12 C27 C28 C29 -176.90(13) . . . . ? C32 C27 C28 C29 59.66(17) . . . . ? C26 C27 C28 C29 -57.25(18) . . . . ? C15 O5 C10 C11 5.7(3) . . . . ? C15 O5 C10 C9 -174.03(18) . . . . ? C18 C19 C20 C21 -1.5(3) . . . . ? C18 C19 C20 C29 178.95(16) . . . . ? C31 C34 C33 C29 61.62(18) . . . . ? C32 C34 C33 C29 -59.70(18) . . . . ? O2 C2 C3 C4 177.92(16) . . . . ? C1 C2 C3 C4 -1.3(3) . . . . ? C12 C27 C26 C25 176.77(13) . . . . ? C32 C27 C26 C25 -59.25(17) . . . . ? C28 C27 C26 C25 57.42(18) . . . . ? O5 C10 C11 C12 -176.70(16) . . . . ? C9 C10 C11 C12 3.1(3) . . . . ? C8 O3 C6 C5 -8.5(2) . . . . ? C8 O3 C6 C1 170.50(16) . . . . ? C4 C5 C6 O3 177.76(16) . . . . ? C4 C5 C6 C1 -1.1(3) . . . . ? O1 C1 C6 O3 -0.4(2) . . . . ? C2 C1 C6 O3 179.50(15) . . . . ? O1 C1 C6 C5 178.60(16) . . . . ? C2 C1 C6 C5 -1.5(3) . . . . ? C19 C20 C21 C22 0.8(3) . . . . ? C29 C20 C21 C22 -179.65(16) . . . . ? C14 C13 C12 C11 -3.0(2) . . . . ? C14 C13 C12 C27 175.27(16) . . . . ? C10 C11 C12 C13 0.5(3) . . . . ? C10 C11 C12 C27 -177.86(16) . . . . ? C32 C27 C12 C13 10.8(2) . . . . ? C26 C27 C12 C13 131.57(17) . . . . ? C28 C27 C12 C13 -109.07(18) . . . . ? C32 C27 C12 C11 -170.95(15) . . . . ? C26 C27 C12 C11 -50.2(2) . . . . ? C28 C27 C12 C11 69.15(19) . . . . ? O5 C10 C9 O4 -4.3(2) . . . . ? C11 C10 C9 O4 175.90(16) . . . . ? O5 C10 C9 C14 175.83(16) . . . . ? C11 C10 C9 C14 -3.9(3) . . . . ? C6 C5 C4 C3 2.5(3) . . . . ? C6 C5 C4 C25 -177.42(16) . . . . ? C2 C3 C4 C5 -1.4(3) . . . . ? C2 C3 C4 C25 178.61(16) . . . . ? C5 C4 C25 C30 179.04(15) . . . . ? C3 C4 C25 C30 -0.9(2) . . . . ? C5 C4 C25 C26 -61.3(2) . . . . ? C3 C4 C25 C26 118.73(18) . . . . ? C5 C4 C25 C31 58.0(2) . . . . ? C3 C4 C25 C31 -121.95(17) . . . . ? C27 C26 C25 C4 -179.67(13) . . . . ? C27 C26 C25 C30 -57.80(17) . . . . ? C27 C26 C25 C31 59.57(18) . . . . ? C32 C34 C31 C25 59.58(18) . . . . ? C33 C34 C31 C25 -61.38(18) . . . . ? C4 C25 C31 C34 -178.25(14) . . . . ? C30 C25 C31 C34 58.75(18) . . . . ? C26 C25 C31 C34 -58.44(18) . . . . ? C23 O8 C18 C19 7.1(3) . . . . ? C23 O8 C18 C17 -174.63(16) . . . . ? C20 C19 C18 O8 178.31(16) . . . . ? C20 C19 C18 C17 0.1(3) . . . . ? O7 C17 C18 O8 1.7(2) . . . . ? C22 C17 C18 O8 -176.50(15) . . . . ? O7 C17 C18 C19 -179.97(16) . . . . ? C22 C17 C18 C19 1.9(3) . . . . ? C4 C25 C30 C29 179.27(14) . . . . ? C26 C25 C30 C29 59.00(18) . . . . ? C31 C25 C30 C29 -58.36(18) . . . . ? C24 O9 C22 C17 -176.68(15) . . . . ? C24 O9 C22 C21 2.2(2) . . . . ? O7 C17 C22 O9 -1.8(2) . . . . ? C18 C17 C22 O9 176.35(15) . . . . ? O7 C17 C22 C21 179.27(16) . . . . ? C18 C17 C22 C21 -2.6(3) . . . . ? C20 C21 C22 O9 -177.55(16) . . . . ? C20 C21 C22 C17 1.3(3) . . . . ? C21 C20 C29 C30 2.4(2) . . . . ? C19 C20 C29 C30 -177.98(15) . . . . ? C21 C20 C29 C28 -117.58(18) . . . . ? C19 C20 C29 C28 62.0(2) . . . . ? C21 C20 C29 C33 122.65(17) . . . . ? C19 C20 C29 C33 -57.8(2) . . . . ? C25 C30 C29 C20 179.96(14) . . . . ? C25 C30 C29 C28 -58.83(18) . . . . ? C25 C30 C29 C33 58.17(18) . . . . ? C27 C28 C29 C20 179.46(13) . . . . ? C27 C28 C29 C30 57.38(17) . . . . ? C27 C28 C29 C33 -59.37(18) . . . . ? C34 C33 C29 C20 179.05(14) . . . . ? C34 C33 C29 C30 -58.62(17) . . . . ? C34 C33 C29 C28 58.22(18) . . . . ? O4 C9 C14 C13 -178.39(16) . . . . ? C10 C9 C14 C13 1.5(3) . . . . ? O4 C9 C14 O6 -1.2(3) . . . . ? C10 C9 C14 O6 178.66(16) . . . . ? C12 C13 C14 C9 2.1(3) . . . . ? C12 C13 C14 O6 -175.03(16) . . . . ? C16 O6 C14 C9 106.30(19) . . . . ? C16 O6 C14 C13 -76.4(2) . . . . ? C31 C34 C32 C27 -59.93(18) . . . . ? C33 C34 C32 C27 60.75(18) . . . . ? C12 C27 C32 C34 179.87(14) . . . . ? C26 C27 C32 C34 58.24(18) . . . . ? C28 C27 C32 C34 -59.39(18) . . . . ? C35 C40 C39 C38 -0.5(3) . . . . ? C35 C40 C39 N3 177.71(17) . . . . ? O14 N3 C39 C40 -174.61(18) . . . . ? O15 N3 C39 C40 5.1(3) . . . . ? O14 N3 C39 C38 3.7(3) . . . . ? O15 N3 C39 C38 -176.57(18) . . . . ? C40 C39 C38 C37 0.3(3) . . . . ? N3 C39 C38 C37 -177.90(17) . . . . ? C39 C38 C37 C36 -0.5(3) . . . . ? C39 C38 C37 N2 179.60(17) . . . . ? C35 C36 C37 C38 0.8(3) . . . . ? C35 C36 C37 N2 -179.26(17) . . . . ? O13 N2 C37 C38 5.7(3) . . . . ? O12 N2 C37 C38 -175.15(18) . . . . ? O13 N2 C37 C36 -174.24(19) . . . . ? O12 N2 C37 C36 4.9(3) . . . . ? C39 C40 C35 C36 0.9(3) . . . . ? C39 C40 C35 N1 -178.73(16) . . . . ? C37 C36 C35 C40 -1.0(3) . . . . ? C37 C36 C35 N1 178.59(17) . . . . ? O11 N1 C35 C40 -161.49(17) . . . . ? O10 N1 C35 C40 19.2(3) . . . . ? O11 N1 C35 C36 18.9(3) . . . . ? O10 N1 C35 C36 -160.48(18) . . . . ? 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 O1 H1 O6 0.84 2.06 2.8452(18) 155.0 2_545 O4 H4 O2 0.84 2.37 2.8402(17) 116.3 4_475 _diffrn_measured_fraction_theta_max 0.898 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.304 _refine_diff_density_min -0.322 _refine_diff_density_rms 0.048 # Attachment '740186.cif' data_a0811151kka _database_code_depnum_ccdc_archive 'CCDC 740186' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C46 H52 Cl12 O12' _chemical_formula_weight 1222.28 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C2/c ' 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 31.279(3) _cell_length_b 10.6127(10) _cell_length_c 22.276(4) _cell_angle_alpha 90.00 _cell_angle_beta 132.3560(10) _cell_angle_gamma 90.00 _cell_volume 5464.5(12) _cell_formula_units_Z 4 _cell_measurement_temperature 120 _cell_measurement_reflns_used 7365 _cell_measurement_theta_min 2.47 _cell_measurement_theta_max 26.91 _exptl_crystal_description prismatic _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.35 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.486 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2512 _exptl_absorpt_coefficient_mu 0.665 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.7767 _exptl_absorpt_correction_T_max 0.8005 _exptl_absorpt_process_details ; SADABS Sheldrick 1996 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 120 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEXII CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.333 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13020 _diffrn_reflns_av_R_equivalents 0.0171 _diffrn_reflns_av_sigmaI/netI 0.0233 _diffrn_reflns_limit_h_min -38 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 27.13 _reflns_number_total 5515 _reflns_number_gt 4840 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2006)' _computing_cell_refinement 'APEX2 (Bruker AXS, 2006)' _computing_data_reduction 'SAINT (Bruker AXS, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XSHEL (Bruker AXS,2002)' _computing_publication_material 'XCIF (Bruker AXS, 2001)' _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^)+(0.0595P)^2^+24.7490P] 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 5515 _refine_ls_number_parameters 323 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0607 _refine_ls_R_factor_gt 0.0543 _refine_ls_wR_factor_ref 0.1421 _refine_ls_wR_factor_gt 0.1370 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C21 C 0.5000 0.3713(3) 0.7500 0.0135(6) Uani 1 2 d S . . H21A H 0.5171 0.3164 0.7974 0.016 Uiso 0.50 1 calc PR . . H21B H 0.4829 0.3164 0.7026 0.016 Uiso 0.50 1 calc PR . . Cl11 Cl 0.65533(8) 0.25551(11) 0.18096(7) 0.0988(6) Uani 1 1 d . . . Cl12 Cl 0.54397(5) 0.25291(10) 0.01558(10) 0.0787(4) Uani 1 1 d . . . Cl8 Cl 0.82126(4) 0.69102(9) 0.12873(7) 0.0527(3) Uani 1 1 d . . . Cl9 Cl 0.71364(4) 0.66415(8) 0.09217(7) 0.0508(3) Uani 1 1 d . . . Cl7 Cl 0.74757(4) 0.47371(9) 0.03895(5) 0.0471(2) Uani 1 1 d . . . Cl10 Cl 0.64484(4) 0.34382(7) 0.05045(5) 0.0374(2) Uani 1 1 d . . . C24 C 0.61879(14) 0.2351(3) 0.07898(19) 0.0316(6) Uani 1 1 d . . . H24 H 0.6268 0.1481 0.0715 0.038 Uiso 1 1 calc R . . C16 C 0.55393(13) 0.0049(3) 0.6741(2) 0.0337(7) Uani 1 1 d . . . H16A H 0.5482 -0.0038 0.7121 0.051 Uiso 1 1 calc R . . H16B H 0.5526 -0.0785 0.6540 0.051 Uiso 1 1 calc R . . H16C H 0.5232 0.0580 0.6283 0.051 Uiso 1 1 calc R . . C23 C 0.77241(13) 0.5839(3) 0.11576(19) 0.0319(6) Uani 1 1 d . . . H23 H 0.7931 0.5372 0.1679 0.038 Uiso 1 1 calc R . . C8 C 0.39513(14) 1.0800(3) 0.59232(18) 0.0301(6) Uani 1 1 d . . . H8A H 0.3706 1.0272 0.5947 0.045 Uiso 1 1 calc R . . H8B H 0.3811 1.1671 0.5802 0.045 Uiso 1 1 calc R . . H8C H 0.4351 1.0771 0.6448 0.045 Uiso 1 1 calc R . . C7 C 0.41131(13) 0.5835(3) 0.39104(17) 0.0261(6) Uani 1 1 d . . . H7A H 0.4502 0.5509 0.4359 0.039 Uiso 1 1 calc R . . H7B H 0.4023 0.5731 0.3398 0.039 Uiso 1 1 calc R . . H7C H 0.3830 0.5371 0.3884 0.039 Uiso 1 1 calc R . . C15 C 0.75309(12) 0.5193(3) 0.8687(2) 0.0307(6) Uani 1 1 d . . . H15A H 0.7213 0.5667 0.8203 0.046 Uiso 1 1 calc R . . H15B H 0.7892 0.5381 0.8815 0.046 Uiso 1 1 calc R . . H15C H 0.7570 0.5434 0.9147 0.046 Uiso 1 1 calc R . . C10 C 0.68743(11) 0.3479(2) 0.82054(15) 0.0205(5) Uani 1 1 d . . . C2 C 0.41659(11) 0.7447(2) 0.47059(15) 0.0173(5) Uani 1 1 d . . . C14 C 0.61938(11) 0.1788(2) 0.74910(15) 0.0183(5) Uani 1 1 d . . . C19 C 0.52026(10) 0.5367(2) 0.69244(14) 0.0143(5) Uani 1 1 d . . . H19A H 0.5504 0.5907 0.7026 0.017 Uiso 1 1 calc R . . H19B H 0.5035 0.4833 0.6446 0.017 Uiso 1 1 calc R . . C22 C 0.57437(10) 0.5357(2) 0.84179(14) 0.0140(5) Uani 1 1 d . . . H22A H 0.5918 0.4817 0.8897 0.017 Uiso 1 1 calc R . . H22B H 0.6054 0.5890 0.8539 0.017 Uiso 1 1 calc R . . C9 C 0.67305(11) 0.2290(2) 0.78591(15) 0.0197(5) Uani 1 1 d . . . C6 C 0.40842(10) 0.9107(2) 0.53497(15) 0.0177(5) Uani 1 1 d . . . C12 C 0.59386(10) 0.3690(2) 0.77969(13) 0.0145(5) Uani 1 1 d . . . C5 C 0.43022(10) 0.8307(2) 0.59938(14) 0.0171(5) Uani 1 1 d . . . H5 H 0.4344 0.8608 0.6433 0.021 Uiso 1 1 calc R . . C13 C 0.58019(10) 0.2481(2) 0.74603(15) 0.0173(5) Uani 1 1 d . . . H13 H 0.5435 0.2128 0.7206 0.021 Uiso 1 1 calc R . . C20 C 0.54815(10) 0.4519(2) 0.76712(14) 0.0134(5) Uani 1 1 d . . . C11 C 0.64859(10) 0.4176(2) 0.81810(14) 0.0178(5) Uani 1 1 d . . . H11 H 0.6593 0.4986 0.8426 0.021 Uiso 1 1 calc R . . C3 C 0.43829(10) 0.6643(2) 0.53495(14) 0.0163(5) Uani 1 1 d . . . H3 H 0.4479 0.5799 0.5339 0.020 Uiso 1 1 calc R . . C1 C 0.40220(10) 0.8686(2) 0.47037(14) 0.0172(5) Uani 1 1 d . . . C4 C 0.44613(10) 0.7067(2) 0.60099(14) 0.0145(5) Uani 1 1 d . . . C17 C 0.47248(10) 0.6204(2) 0.67416(13) 0.0135(4) Uani 1 1 d . . . C18 C 0.5000 0.7005(3) 0.7500 0.0146(6) Uani 1 2 d S . . H18A H 0.4700 0.7555 0.7395 0.018 Uiso 0.50 1 calc PR . . H18B H 0.5300 0.7555 0.7605 0.018 Uiso 0.50 1 calc PR . . O5 O 0.74122(8) 0.38776(19) 0.85353(14) 0.0313(5) Uani 1 1 d . . . O4 O 0.70930(8) 0.16047(18) 0.78393(13) 0.0270(4) Uani 1 1 d . . . H4 H 0.7403 0.2004 0.8081 0.040 Uiso 1 1 calc R . . O2 O 0.40905(9) 0.71400(17) 0.40414(11) 0.0237(4) Uani 1 1 d . . . O6 O 0.60908(8) 0.06199(17) 0.71490(12) 0.0245(4) Uani 1 1 d . . . O3 O 0.39309(9) 1.03427(17) 0.53011(11) 0.0247(4) Uani 1 1 d . . . O1 O 0.38170(9) 0.95071(17) 0.40855(11) 0.0227(4) Uani 1 1 d . . . H1 H 0.3771 0.9124 0.3715 0.034 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C21 0.0151(15) 0.0136(15) 0.0129(15) 0.000 0.0099(13) 0.000 Cl11 0.1983(17) 0.0449(6) 0.0530(6) -0.0183(5) 0.0846(9) -0.0400(8) Cl12 0.0479(6) 0.0416(5) 0.1473(12) -0.0107(6) 0.0661(7) -0.0051(4) Cl8 0.0425(5) 0.0377(5) 0.0863(7) -0.0002(4) 0.0468(5) -0.0062(4) Cl9 0.0345(4) 0.0368(4) 0.0807(7) 0.0067(4) 0.0386(5) 0.0053(3) Cl7 0.0527(5) 0.0505(5) 0.0403(5) -0.0071(4) 0.0322(4) -0.0110(4) Cl10 0.0434(4) 0.0267(4) 0.0475(5) 0.0014(3) 0.0328(4) -0.0011(3) C24 0.0388(16) 0.0210(14) 0.0379(16) -0.0039(12) 0.0270(15) -0.0040(12) C16 0.0268(14) 0.0257(15) 0.0472(18) -0.0136(13) 0.0244(14) -0.0059(12) C23 0.0276(14) 0.0275(15) 0.0383(16) 0.0053(13) 0.0212(13) 0.0015(12) C8 0.0517(18) 0.0196(13) 0.0326(15) 0.0013(11) 0.0339(15) 0.0078(12) C7 0.0445(16) 0.0174(13) 0.0237(13) 0.0007(10) 0.0259(13) 0.0054(11) C15 0.0230(13) 0.0243(14) 0.0433(17) -0.0007(12) 0.0217(13) -0.0033(11) C10 0.0147(11) 0.0232(13) 0.0210(12) 0.0019(10) 0.0110(10) 0.0010(10) C2 0.0205(12) 0.0185(12) 0.0160(11) 0.0006(9) 0.0136(10) 0.0010(9) C14 0.0209(12) 0.0169(12) 0.0174(11) 0.0015(9) 0.0130(10) 0.0027(9) C19 0.0162(11) 0.0158(11) 0.0137(11) 0.0002(9) 0.0112(9) 0.0010(9) C22 0.0145(11) 0.0155(11) 0.0132(11) -0.0012(9) 0.0098(9) -0.0009(9) C9 0.0187(12) 0.0216(12) 0.0209(12) 0.0053(10) 0.0141(11) 0.0070(10) C6 0.0195(12) 0.0149(11) 0.0198(12) 0.0002(9) 0.0137(10) 0.0018(9) C12 0.0158(11) 0.0175(11) 0.0114(10) 0.0024(9) 0.0097(9) 0.0017(9) C5 0.0205(12) 0.0180(12) 0.0156(11) -0.0005(9) 0.0133(10) 0.0013(9) C13 0.0177(11) 0.0169(12) 0.0190(12) 0.0011(9) 0.0131(10) 0.0008(9) C20 0.0147(11) 0.0135(11) 0.0130(10) 0.0000(9) 0.0097(9) -0.0001(9) C11 0.0181(11) 0.0174(12) 0.0171(11) -0.0004(9) 0.0115(10) 0.0003(9) C3 0.0201(12) 0.0144(11) 0.0169(11) 0.0013(9) 0.0135(10) 0.0025(9) C1 0.0192(12) 0.0174(12) 0.0163(11) 0.0036(9) 0.0125(10) 0.0017(9) C4 0.0143(11) 0.0163(11) 0.0136(11) 0.0014(9) 0.0097(9) -0.0002(9) C17 0.0157(11) 0.0141(11) 0.0118(10) 0.0007(9) 0.0098(9) 0.0007(9) C18 0.0177(16) 0.0141(15) 0.0129(15) 0.000 0.0106(14) 0.000 O5 0.0200(9) 0.0239(10) 0.0495(13) -0.0052(9) 0.0232(10) -0.0015(8) O4 0.0224(9) 0.0240(10) 0.0401(12) -0.0004(8) 0.0233(9) 0.0036(8) O2 0.0415(11) 0.0173(9) 0.0207(9) 0.0038(7) 0.0243(9) 0.0077(8) O6 0.0221(9) 0.0192(9) 0.0325(10) -0.0057(8) 0.0185(9) 0.0003(7) O3 0.0407(11) 0.0157(9) 0.0234(9) 0.0035(7) 0.0239(9) 0.0085(8) O1 0.0372(11) 0.0166(9) 0.0203(9) 0.0052(7) 0.0218(9) 0.0070(8) _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 C21 C20 1.539(3) . ? C21 C20 1.539(3) 2_656 ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? Cl11 C24 1.737(3) . ? Cl12 C24 1.748(3) . ? Cl8 C23 1.765(3) . ? Cl9 C23 1.755(3) . ? Cl7 C23 1.763(3) . ? Cl10 C24 1.760(3) . ? C24 H24 1.0000 . ? C16 O6 1.434(3) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C23 H23 1.0000 . ? C8 O3 1.429(3) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C7 O2 1.426(3) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C15 O5 1.425(3) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C10 O5 1.372(3) . ? C10 C9 1.386(4) . ? C10 C11 1.392(4) . ? C2 O2 1.372(3) . ? C2 C1 1.389(3) . ? C2 C3 1.390(3) . ? C14 O6 1.375(3) . ? C14 C9 1.385(4) . ? C14 C13 1.391(3) . ? C19 C17 1.539(3) . ? C19 C20 1.544(3) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C22 C17 1.543(3) 2_656 ? C22 C20 1.547(3) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C9 O4 1.373(3) . ? C6 O3 1.375(3) . ? C6 C5 1.388(3) . ? C6 C1 1.390(3) . ? C12 C11 1.398(3) . ? C12 C13 1.399(3) . ? C12 C20 1.536(3) . ? C5 C4 1.399(3) . ? C5 H5 0.9500 . ? C13 H13 0.9500 . ? C11 H11 0.9500 . ? C3 C4 1.393(3) . ? C3 H3 0.9500 . ? C1 O1 1.370(3) . ? C4 C17 1.538(3) . ? C17 C18 1.536(3) . ? C17 C22 1.543(3) 2_656 ? C18 C17 1.536(3) 2_656 ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? O4 H4 0.8400 . ? O1 H1 0.8400 . ? 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 C20 C21 C20 112.6(3) . 2_656 ? C20 C21 H21A 109.1 . . ? C20 C21 H21A 109.1 2_656 . ? C20 C21 H21B 109.1 . . ? C20 C21 H21B 109.1 2_656 . ? H21A C21 H21B 107.8 . . ? Cl11 C24 Cl12 112.72(19) . . ? Cl11 C24 Cl10 109.51(17) . . ? Cl12 C24 Cl10 109.34(18) . . ? Cl11 C24 H24 108.4 . . ? Cl12 C24 H24 108.4 . . ? Cl10 C24 H24 108.4 . . ? O6 C16 H16A 109.5 . . ? O6 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? O6 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? Cl9 C23 Cl7 110.10(17) . . ? Cl9 C23 Cl8 110.66(17) . . ? Cl7 C23 Cl8 110.66(18) . . ? Cl9 C23 H23 108.4 . . ? Cl7 C23 H23 108.4 . . ? Cl8 C23 H23 108.4 . . ? O3 C8 H8A 109.5 . . ? O3 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? O3 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? O2 C7 H7A 109.5 . . ? O2 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? O2 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? O5 C15 H15A 109.5 . . ? O5 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? O5 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? O5 C10 C9 113.5(2) . . ? O5 C10 C11 125.5(2) . . ? C9 C10 C11 121.0(2) . . ? O2 C2 C1 113.7(2) . . ? O2 C2 C3 125.2(2) . . ? C1 C2 C3 121.1(2) . . ? O6 C14 C9 114.4(2) . . ? O6 C14 C13 125.4(2) . . ? C9 C14 C13 120.1(2) . . ? C17 C19 C20 111.39(18) . . ? C17 C19 H19A 109.3 . . ? C20 C19 H19A 109.3 . . ? C17 C19 H19B 109.3 . . ? C20 C19 H19B 109.3 . . ? H19A C19 H19B 108.0 . . ? C17 C22 C20 110.75(18) 2_656 . ? C17 C22 H22A 109.5 2_656 . ? C20 C22 H22A 109.5 . . ? C17 C22 H22B 109.5 2_656 . ? C20 C22 H22B 109.5 . . ? H22A C22 H22B 108.1 . . ? O4 C9 C14 118.3(2) . . ? O4 C9 C10 122.3(2) . . ? C14 C9 C10 119.3(2) . . ? O3 C6 C5 124.5(2) . . ? O3 C6 C1 115.3(2) . . ? C5 C6 C1 120.2(2) . . ? C11 C12 C13 118.2(2) . . ? C11 C12 C20 120.4(2) . . ? C13 C12 C20 121.1(2) . . ? C6 C5 C4 121.4(2) . . ? C6 C5 H5 119.3 . . ? C4 C5 H5 119.3 . . ? C14 C13 C12 121.1(2) . . ? C14 C13 H13 119.4 . . ? C12 C13 H13 119.4 . . ? C12 C20 C21 111.24(19) . . ? C12 C20 C19 108.14(18) . . ? C21 C20 C19 107.97(17) . . ? C12 C20 C22 112.30(18) . . ? C21 C20 C22 107.89(17) . . ? C19 C20 C22 109.20(19) . . ? C10 C11 C12 120.3(2) . . ? C10 C11 H11 119.9 . . ? C12 C11 H11 119.9 . . ? C2 C3 C4 120.5(2) . . ? C2 C3 H3 119.8 . . ? C4 C3 H3 119.8 . . ? O1 C1 C2 122.5(2) . . ? O1 C1 C6 118.7(2) . . ? C2 C1 C6 118.8(2) . . ? C3 C4 C5 118.1(2) . . ? C3 C4 C17 120.9(2) . . ? C5 C4 C17 121.0(2) . . ? C18 C17 C4 109.8(2) . . ? C18 C17 C19 107.69(17) . . ? C4 C17 C19 110.85(18) . . ? C18 C17 C22 108.51(17) . 2_656 ? C4 C17 C22 110.81(18) . 2_656 ? C19 C17 C22 109.06(19) . 2_656 ? C17 C18 C17 112.8(3) . 2_656 ? C17 C18 H18A 109.0 . . ? C17 C18 H18A 109.0 2_656 . ? C17 C18 H18B 109.0 . . ? C17 C18 H18B 109.0 2_656 . ? H18A C18 H18B 107.8 . . ? C10 O5 C15 117.3(2) . . ? C9 O4 H4 109.5 . . ? C2 O2 C7 117.1(2) . . ? C14 O6 C16 117.7(2) . . ? C6 O3 C8 117.5(2) . . ? C1 O1 H1 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O6 C14 C9 O4 0.8(3) . . . . ? C13 C14 C9 O4 -176.6(2) . . . . ? O6 C14 C9 C10 178.3(2) . . . . ? C13 C14 C9 C10 0.9(4) . . . . ? O5 C10 C9 O4 -1.3(4) . . . . ? C11 C10 C9 O4 176.8(2) . . . . ? O5 C10 C9 C14 -178.8(2) . . . . ? C11 C10 C9 C14 -0.6(4) . . . . ? O3 C6 C5 C4 -178.5(2) . . . . ? C1 C6 C5 C4 -0.3(4) . . . . ? O6 C14 C13 C12 -177.1(2) . . . . ? C9 C14 C13 C12 0.0(4) . . . . ? C11 C12 C13 C14 -1.2(3) . . . . ? C20 C12 C13 C14 172.3(2) . . . . ? C11 C12 C20 C21 -161.66(19) . . . . ? C13 C12 C20 C21 24.9(3) . . . . ? C11 C12 C20 C19 79.9(3) . . . . ? C13 C12 C20 C19 -93.5(3) . . . . ? C11 C12 C20 C22 -40.6(3) . . . . ? C13 C12 C20 C22 146.0(2) . . . . ? C20 C21 C20 C12 -177.1(2) 2_656 . . . ? C20 C21 C20 C19 -58.63(14) 2_656 . . . ? C20 C21 C20 C22 59.27(14) 2_656 . . . ? C17 C19 C20 C12 178.34(18) . . . . ? C17 C19 C20 C21 57.9(2) . . . . ? C17 C19 C20 C22 -59.2(2) . . . . ? C17 C22 C20 C12 178.25(18) 2_656 . . . ? C17 C22 C20 C21 -58.8(2) 2_656 . . . ? C17 C22 C20 C19 58.3(2) 2_656 . . . ? O5 C10 C11 C12 177.3(2) . . . . ? C9 C10 C11 C12 -0.7(4) . . . . ? C13 C12 C11 C10 1.6(4) . . . . ? C20 C12 C11 C10 -172.0(2) . . . . ? O2 C2 C3 C4 177.7(2) . . . . ? C1 C2 C3 C4 0.0(4) . . . . ? O2 C2 C1 O1 0.9(3) . . . . ? C3 C2 C1 O1 178.8(2) . . . . ? O2 C2 C1 C6 -179.6(2) . . . . ? C3 C2 C1 C6 -1.7(4) . . . . ? O3 C6 C1 O1 -0.2(3) . . . . ? C5 C6 C1 O1 -178.6(2) . . . . ? O3 C6 C1 C2 -179.8(2) . . . . ? C5 C6 C1 C2 1.8(4) . . . . ? C2 C3 C4 C5 1.5(3) . . . . ? C2 C3 C4 C17 -177.4(2) . . . . ? C6 C5 C4 C3 -1.4(4) . . . . ? C6 C5 C4 C17 177.6(2) . . . . ? C3 C4 C17 C18 155.73(19) . . . . ? C5 C4 C17 C18 -23.2(3) . . . . ? C3 C4 C17 C19 36.8(3) . . . . ? C5 C4 C17 C19 -142.1(2) . . . . ? C3 C4 C17 C22 -84.4(3) . . . 2_656 ? C5 C4 C17 C22 96.7(3) . . . 2_656 ? C20 C19 C17 C18 58.4(2) . . . . ? C20 C19 C17 C4 178.59(19) . . . . ? C20 C19 C17 C22 -59.1(2) . . . 2_656 ? C4 C17 C18 C17 -179.8(2) . . . 2_656 ? C19 C17 C18 C17 -58.96(14) . . . 2_656 ? C22 C17 C18 C17 58.97(14) 2_656 . . 2_656 ? C9 C10 O5 C15 162.1(2) . . . . ? C11 C10 O5 C15 -16.0(4) . . . . ? C1 C2 O2 C7 -167.5(2) . . . . ? C3 C2 O2 C7 14.7(4) . . . . ? C9 C14 O6 C16 -178.7(2) . . . . ? C13 C14 O6 C16 -1.5(4) . . . . ? C5 C6 O3 C8 -5.6(4) . . . . ? C1 C6 O3 C8 176.1(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 O1 H1 O6 0.84 2.26 2.955(3) 140.7 5_666 O4 H4 Cl10 0.84 2.79 3.427(2) 133.6 7_656 _diffrn_measured_fraction_theta_max 0.909 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 2.169 _refine_diff_density_min -1.563 _refine_diff_density_rms 0.077 # Attachment '740187.cif' data_a0906221kka _database_code_depnum_ccdc_archive 'CCDC 740187' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C55 H55 Cl3 N6 O24' _chemical_formula_weight 1290.40 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P-1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 13.052(14) _cell_length_b 14.340(15) _cell_length_c 16.268(17) _cell_angle_alpha 102.717(15) _cell_angle_beta 91.783(13) _cell_angle_gamma 107.300(13) _cell_volume 2821(5) _cell_formula_units_Z 2 _cell_measurement_temperature 120 _cell_measurement_reflns_used 2328 _cell_measurement_theta_min 0.00 _cell_measurement_theta_max 0.00 _exptl_crystal_description plate _exptl_crystal_colour red _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.519 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1340 _exptl_absorpt_coefficient_mu 0.255 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9160 _exptl_absorpt_correction_T_max 0.9874 _exptl_absorpt_process_details ; SADABS Sheldrick 1996 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 120 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEXII CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.333 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13258 _diffrn_reflns_av_R_equivalents 0.0460 _diffrn_reflns_av_sigmaI/netI 0.1298 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.98 _diffrn_reflns_theta_max 26.99 _reflns_number_total 10415 _reflns_number_gt 5247 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2006)' _computing_cell_refinement 'APEX2 (Bruker AXS, 2006)' _computing_data_reduction 'SAINT (Bruker AXS, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XSHEL (Bruker AXS,2002)' _computing_publication_material 'XCIF (Bruker AXS, 2001)' _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^)+(0.1325P)^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 10415 _refine_ls_number_parameters 829 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1627 _refine_ls_R_factor_gt 0.0785 _refine_ls_wR_factor_ref 0.2500 _refine_ls_wR_factor_gt 0.2009 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_restrained_S_all 1.006 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.1030(4) 0.4595(3) 0.54786(19) 0.0892(13) Uani 0.733(6) 1 d P A 1 Cl2 Cl 0.2387(2) 0.3449(3) 0.47769(16) 0.0749(12) Uani 0.733(6) 1 d P A 1 Cl3 Cl 0.0094(2) 0.2499(3) 0.4764(2) 0.0772(12) Uani 0.733(6) 1 d P A 1 Cl1B Cl 0.1928(14) 0.4433(13) 0.5229(10) 0.175(8) Uani 0.267(6) 1 d P A 2 Cl2B Cl -0.007(2) 0.3734(19) 0.5259(12) 0.250(12) Uani 0.267(6) 1 d P A 2 Cl3B Cl 0.087(4) 0.2277(17) 0.4483(10) 0.38(3) Uani 0.267(6) 1 d P A 2 C1 C 0.4553(4) 0.6444(4) 0.5875(3) 0.0293(12) Uani 1 1 d . . . C2 C 0.4455(4) 0.7394(4) 0.5925(3) 0.0278(12) Uani 1 1 d . . . C3 C 0.3815(4) 0.7770(3) 0.6468(3) 0.0226(11) Uani 1 1 d . . . H3 H 0.3755 0.8418 0.6484 0.027 Uiso 1 1 calc R . . C4 C 0.3248(4) 0.7198(3) 0.6999(3) 0.0211(11) Uani 1 1 d . . . C5 C 0.3360(4) 0.6246(3) 0.6966(3) 0.0240(11) Uani 1 1 d . . . H5 H 0.2980 0.5846 0.7320 0.029 Uiso 1 1 calc R . . C6 C 0.4026(4) 0.5890(3) 0.6415(3) 0.0254(12) Uani 1 1 d . . . C7 C 0.5008(6) 0.8867(4) 0.5397(4) 0.0536(18) Uani 1 1 d . . . H7A H 0.4259 0.8839 0.5266 0.080 Uiso 1 1 calc R . . H7B H 0.5450 0.9134 0.4975 0.080 Uiso 1 1 calc R . . H7C H 0.5286 0.9307 0.5961 0.080 Uiso 1 1 calc R . . C8 C 0.3613(5) 0.4338(4) 0.6885(4) 0.0423(15) Uani 1 1 d . . . H8A H 0.3758 0.4710 0.7481 0.063 Uiso 1 1 calc R . . H8B H 0.3840 0.3735 0.6818 0.063 Uiso 1 1 calc R . . H8C H 0.2839 0.4141 0.6707 0.063 Uiso 1 1 calc R . . C9 C 0.2238(4) 1.2152(4) 0.8240(3) 0.0276(12) Uani 1 1 d . . . C10 C 0.2173(4) 1.1851(3) 0.8973(3) 0.0255(12) Uani 1 1 d . . . C11 C 0.2015(4) 1.0850(3) 0.8968(3) 0.0229(11) Uani 1 1 d . . . H11 H 0.1996 1.0655 0.9490 0.028 Uiso 1 1 calc R . . C12 C 0.1884(4) 1.0125(3) 0.8212(3) 0.0234(11) Uani 1 1 d . . . C13 C 0.1889(4) 1.0442(4) 0.7469(3) 0.0282(12) Uani 1 1 d . . . H13 H 0.1754 0.9961 0.6941 0.034 Uiso 1 1 calc R . . C14 C 0.2088(4) 1.1460(4) 0.7483(3) 0.0289(12) Uani 1 1 d . . . C15 C 0.2238(5) 1.2400(4) 1.0495(3) 0.0349(13) Uani 1 1 d . . . H15A H 0.1542 1.1905 1.0516 0.052 Uiso 1 1 calc R . . H15B H 0.2326 1.3018 1.0931 0.052 Uiso 1 1 calc R . . H15C H 0.2821 1.2125 1.0597 0.052 Uiso 1 1 calc R . . C16 C 0.1992(6) 1.1158(5) 0.5983(4) 0.0517(17) Uani 1 1 d . . . H16A H 0.2530 1.0803 0.5964 0.078 Uiso 1 1 calc R . . H16B H 0.2082 1.1529 0.5538 0.078 Uiso 1 1 calc R . . H16C H 0.1266 1.0669 0.5894 0.078 Uiso 1 1 calc R . . C17 C 0.2665(4) 0.7616(3) 1.1650(3) 0.0207(11) Uani 1 1 d . . . C18 C 0.2144(4) 0.6757(3) 1.1019(3) 0.0204(11) Uani 1 1 d . . . C19 C 0.1905(4) 0.6803(3) 1.0203(3) 0.0226(11) Uani 1 1 d . . . H19 H 0.1534 0.6204 0.9789 0.027 Uiso 1 1 calc R . . C20 C 0.2206(4) 0.7729(3) 0.9980(3) 0.0197(10) Uani 1 1 d . . . C21 C 0.2776(4) 0.8596(3) 1.0607(3) 0.0213(11) Uani 1 1 d . . . H21 H 0.3009 0.9231 1.0467 0.026 Uiso 1 1 calc R . . C22 C 0.2997(4) 0.8529(3) 1.1421(3) 0.0214(11) Uani 1 1 d . . . C23 C 0.1394(4) 0.4951(3) 1.0721(3) 0.0279(12) Uani 1 1 d . . . H23A H 0.0674 0.4935 1.0515 0.042 Uiso 1 1 calc R . . H23B H 0.1329 0.4403 1.1005 0.042 Uiso 1 1 calc R . . H23C H 0.1823 0.4869 1.0242 0.042 Uiso 1 1 calc R . . C24 C 0.4014(4) 1.0287(3) 1.1860(3) 0.0289(12) Uani 1 1 d . . . H24A H 0.4505 1.0211 1.1424 0.043 Uiso 1 1 calc R . . H24B H 0.4414 1.0790 1.2366 0.043 Uiso 1 1 calc R . . H24C H 0.3438 1.0506 1.1643 0.043 Uiso 1 1 calc R . . C25 C -0.2773(4) 0.5240(3) 0.6963(3) 0.0243(11) Uani 1 1 d . . . C26 C -0.2565(4) 0.6267(4) 0.7227(3) 0.0268(12) Uani 1 1 d . . . C27 C -0.1534(4) 0.6919(4) 0.7490(3) 0.0234(11) Uani 1 1 d . . . H27 H -0.1417 0.7624 0.7662 0.028 Uiso 1 1 calc R . . C28 C -0.0659(4) 0.6540(3) 0.7502(3) 0.0213(11) Uani 1 1 d . . . C29 C -0.0872(4) 0.5504(3) 0.7234(3) 0.0237(11) Uani 1 1 d . . . H29 H -0.0294 0.5229 0.7237 0.028 Uiso 1 1 calc R . . C30 C -0.1913(4) 0.4866(3) 0.6962(3) 0.0231(11) Uani 1 1 d . . . C31 C -0.3364(5) 0.7600(4) 0.7385(4) 0.0438(16) Uani 1 1 d . . . H31A H -0.2994 0.7925 0.7956 0.066 Uiso 1 1 calc R . . H31B H -0.4077 0.7695 0.7353 0.066 Uiso 1 1 calc R . . H31C H -0.2938 0.7901 0.6970 0.066 Uiso 1 1 calc R . . C32 C -0.2503(5) 0.3369(4) 0.5851(3) 0.0415(15) Uani 1 1 d . . . H32A H -0.3252 0.3368 0.5774 0.062 Uiso 1 1 calc R . . H32B H -0.2481 0.2676 0.5706 0.062 Uiso 1 1 calc R . . H32C H -0.2071 0.3748 0.5480 0.062 Uiso 1 1 calc R . . C33 C 0.2485(4) 0.7566(3) 0.7595(3) 0.0212(11) Uani 1 1 d . . . C34 C 0.2556(4) 0.8660(3) 0.7616(3) 0.0223(11) Uani 1 1 d . . . H34A H 0.2393 0.8716 0.7034 0.027 Uiso 1 1 calc R . . H34B H 0.3301 0.9102 0.7823 0.027 Uiso 1 1 calc R . . C35 C 0.1763(4) 0.9021(3) 0.8193(3) 0.0201(11) Uani 1 1 d . . . C36 C 0.2028(4) 0.8905(3) 0.9071(3) 0.0203(11) Uani 1 1 d . . . H36A H 0.1534 0.9137 0.9455 0.024 Uiso 1 1 calc R . . H36B H 0.2773 0.9341 0.9287 0.024 Uiso 1 1 calc R . . C37 C 0.1934(4) 0.7810(3) 0.9090(3) 0.0193(10) Uani 1 1 d . . . C38 C 0.2724(4) 0.7480(3) 0.8488(3) 0.0189(10) Uani 1 1 d . . . H38A H 0.3472 0.7905 0.8707 0.023 Uiso 1 1 calc R . . H38B H 0.2672 0.6774 0.8476 0.023 Uiso 1 1 calc R . . C39 C 0.1306(4) 0.6911(3) 0.7255(3) 0.0191(10) Uani 1 1 d . . . H39A H 0.1145 0.6976 0.6675 0.023 Uiso 1 1 calc R . . H39B H 0.1228 0.6196 0.7224 0.023 Uiso 1 1 calc R . . C40 C 0.0493(4) 0.7233(3) 0.7829(3) 0.0194(10) Uani 1 1 d . . . C41 C 0.0779(4) 0.7143(3) 0.8728(3) 0.0201(11) Uani 1 1 d . . . H41A H 0.0261 0.7342 0.9106 0.024 Uiso 1 1 calc R . . H41B H 0.0711 0.6433 0.8712 0.024 Uiso 1 1 calc R . . C42 C 0.0614(4) 0.8347(3) 0.7861(3) 0.0201(10) Uani 1 1 d . . . H42A H 0.0434 0.8415 0.7286 0.024 Uiso 1 1 calc R . . H42B H 0.0101 0.8565 0.8234 0.024 Uiso 1 1 calc R . . C43 C 0.4564(4) 0.6287(3) 0.0975(3) 0.0296(13) Uani 1 1 d . . . C44 C 0.4749(4) 0.6723(4) 0.1823(3) 0.0293(12) Uani 1 1 d . . . H44 H 0.4599 0.6329 0.2230 0.035 Uiso 1 1 calc R . . C45 C 0.5163(4) 0.7764(4) 0.2067(3) 0.0252(12) Uani 1 1 d . . . C46 C 0.5358(4) 0.8346(4) 0.1476(3) 0.0266(12) Uani 1 1 d . . . H46 H 0.5625 0.9060 0.1646 0.032 Uiso 1 1 calc R . . C47 C 0.5147(4) 0.7845(4) 0.0634(3) 0.0262(12) Uani 1 1 d . . . C48 C 0.4740(4) 0.6813(4) 0.0367(3) 0.0278(12) Uani 1 1 d . . . H48 H 0.4588 0.6484 -0.0218 0.033 Uiso 1 1 calc R . . C49 C 0.8847(5) 0.1168(4) 0.6880(4) 0.0393(15) Uani 1 1 d . . . C50 C 0.8815(5) 0.0631(4) 0.7484(4) 0.0387(14) Uani 1 1 d . . . H50 H 0.8441 -0.0070 0.7366 0.046 Uiso 1 1 calc R . . C51 C 0.9348(4) 0.1151(4) 0.8267(3) 0.0292(12) Uani 1 1 d . . . C52 C 0.9907(4) 0.2179(4) 0.8457(3) 0.0277(12) Uani 1 1 d . . . H52 H 1.0259 0.2530 0.9006 0.033 Uiso 1 1 calc R . . C53 C 0.9925(4) 0.2659(4) 0.7811(3) 0.0286(12) Uani 1 1 d . . . C54 C 0.9417(5) 0.2177(4) 0.7016(4) 0.0373(14) Uani 1 1 d . . . H54 H 0.9455 0.2521 0.6577 0.045 Uiso 1 1 calc R . . C55 C 0.1075(6) 0.3563(6) 0.4686(5) 0.069(2) Uani 1 1 d . . . H55 H 0.0940 0.3698 0.4122 0.083 Uiso 1 1 calc R A 1 N1 N 0.4109(4) 0.5175(4) 0.0696(4) 0.0409(13) Uani 1 1 d . . . N2 N 0.5363(4) 0.8288(4) 0.2961(3) 0.0367(11) Uani 1 1 d . . . N3 N 0.5355(3) 0.8434(3) -0.0004(3) 0.0324(11) Uani 1 1 d . . . N4 N 0.8250(5) 0.0631(5) 0.6056(4) 0.0620(17) Uani 1 1 d . . . N5 N 0.9324(4) 0.0617(3) 0.8933(3) 0.0337(11) Uani 1 1 d . . . N6 N 1.0526(4) 0.3744(3) 0.7988(3) 0.0318(11) Uani 1 1 d . . . O1 O 0.5189(3) 0.6089(3) 0.5310(2) 0.0378(10) Uani 1 1 d . . . H1 H 0.5186 0.5517 0.5359 0.057 Uiso 1 1 calc R . . O2 O 0.5049(3) 0.7874(3) 0.5380(3) 0.0456(11) Uani 1 1 d . . . O3 O 0.4216(3) 0.4980(2) 0.6361(2) 0.0308(9) Uani 1 1 d . . . O4 O 0.2463(3) 1.3166(2) 0.8251(2) 0.0372(10) Uani 1 1 d . . . H4 H 0.2539 1.3502 0.8754 0.056 Uiso 1 1 calc R . . O5 O 0.2276(3) 1.2618(2) 0.9684(2) 0.0351(9) Uani 1 1 d . . . O6 O 0.2131(4) 1.1838(3) 0.6783(2) 0.0441(11) Uani 1 1 d . . . O7 O 0.2898(3) 0.7608(2) 1.2461(2) 0.0250(8) Uani 1 1 d . . . H7 H 0.2680 0.7015 1.2517 0.038 Uiso 1 1 calc R . . O8 O 0.1913(3) 0.5892(2) 1.1306(2) 0.0285(8) Uani 1 1 d . . . O9 O 0.3551(3) 0.9341(2) 1.2071(2) 0.0270(8) Uani 1 1 d . . . O10 O -0.3795(3) 0.4598(2) 0.6716(2) 0.0313(9) Uani 1 1 d . . . H10 H -0.4232 0.4929 0.6754 0.047 Uiso 1 1 calc R . . O11 O -0.3488(3) 0.6553(2) 0.7205(2) 0.0346(9) Uani 1 1 d . . . O12 O -0.2072(3) 0.3834(2) 0.6719(2) 0.0277(8) Uani 1 1 d . . . O13 O 0.3793(3) 0.4818(3) -0.0053(3) 0.0481(12) Uani 1 1 d . . . O14 O 0.4098(4) 0.4692(3) 0.1218(3) 0.0579(13) Uani 1 1 d . . . O15 O 0.5245(4) 0.7755(3) 0.3466(3) 0.0537(12) Uani 1 1 d . . . O16 O 0.5650(3) 0.9210(3) 0.3151(2) 0.0439(11) Uani 1 1 d . . . O17 O 0.5562(3) 0.9354(3) 0.0246(3) 0.0446(10) Uani 1 1 d . . . O18 O 0.5328(3) 0.7983(3) -0.0737(3) 0.0440(10) Uani 1 1 d . . . O19 O 0.8233(5) 0.1105(4) 0.5524(3) 0.0747(16) Uani 1 1 d . . . O20 O 0.7765(5) -0.0283(4) 0.5938(3) 0.0904(19) Uani 1 1 d . . . O21 O 0.8762(3) -0.0272(3) 0.8770(3) 0.0452(11) Uani 1 1 d . . . O22 O 0.9843(3) 0.1073(3) 0.9612(2) 0.0378(9) Uani 1 1 d . . . O23 O 1.0723(3) 0.4216(3) 0.8727(3) 0.0417(10) Uani 1 1 d . . . O24 O 1.0768(3) 0.4101(3) 0.7380(3) 0.0433(10) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.108(3) 0.098(3) 0.068(2) 0.0241(16) 0.0180(19) 0.039(2) Cl2 0.0349(15) 0.142(3) 0.0615(18) 0.0468(17) 0.0135(11) 0.0317(16) Cl3 0.0559(19) 0.086(2) 0.072(2) 0.0320(16) -0.0025(13) -0.0136(15) Cl1B 0.122(14) 0.210(16) 0.145(12) 0.031(11) -0.044(10) -0.004(12) Cl2B 0.34(4) 0.29(3) 0.170(17) 0.104(17) 0.11(2) 0.13(3) Cl3B 0.93(8) 0.23(2) 0.067(10) 0.049(10) 0.00(2) 0.30(4) C1 0.020(3) 0.030(3) 0.037(3) 0.000(2) 0.010(2) 0.011(2) C2 0.021(3) 0.030(3) 0.033(3) 0.011(2) 0.017(2) 0.005(2) C3 0.019(3) 0.014(2) 0.035(3) 0.006(2) 0.009(2) 0.005(2) C4 0.011(2) 0.016(2) 0.036(3) 0.004(2) 0.004(2) 0.0036(19) C5 0.013(3) 0.024(3) 0.035(3) 0.003(2) 0.005(2) 0.009(2) C6 0.021(3) 0.016(3) 0.041(3) 0.002(2) 0.006(2) 0.010(2) C7 0.063(5) 0.032(3) 0.071(5) 0.017(3) 0.029(4) 0.016(3) C8 0.037(4) 0.028(3) 0.072(4) 0.022(3) 0.020(3) 0.015(3) C9 0.019(3) 0.018(3) 0.051(3) 0.014(2) 0.016(2) 0.009(2) C10 0.010(2) 0.017(3) 0.048(3) 0.006(2) 0.008(2) 0.003(2) C11 0.009(2) 0.015(2) 0.046(3) 0.007(2) 0.010(2) 0.0057(19) C12 0.009(2) 0.018(3) 0.046(3) 0.012(2) 0.011(2) 0.0043(19) C13 0.021(3) 0.024(3) 0.042(3) 0.010(2) 0.014(2) 0.007(2) C14 0.029(3) 0.028(3) 0.039(3) 0.019(2) 0.017(2) 0.014(2) C15 0.029(3) 0.028(3) 0.046(4) 0.005(2) 0.009(3) 0.009(2) C16 0.069(5) 0.047(4) 0.043(4) 0.014(3) 0.006(3) 0.019(3) C17 0.015(3) 0.019(3) 0.033(3) 0.012(2) 0.013(2) 0.008(2) C18 0.014(3) 0.014(2) 0.036(3) 0.012(2) 0.012(2) 0.003(2) C19 0.015(3) 0.015(2) 0.038(3) 0.008(2) 0.010(2) 0.003(2) C20 0.011(2) 0.020(3) 0.034(3) 0.010(2) 0.012(2) 0.010(2) C21 0.013(2) 0.011(2) 0.039(3) 0.0041(19) 0.008(2) 0.0017(19) C22 0.013(3) 0.017(3) 0.032(3) 0.002(2) 0.009(2) 0.005(2) C23 0.027(3) 0.014(3) 0.042(3) 0.009(2) 0.009(2) 0.004(2) C24 0.023(3) 0.016(3) 0.043(3) 0.008(2) 0.003(2) -0.001(2) C25 0.017(3) 0.019(3) 0.033(3) 0.001(2) 0.006(2) 0.002(2) C26 0.017(3) 0.027(3) 0.040(3) 0.008(2) 0.009(2) 0.011(2) C27 0.014(3) 0.021(3) 0.038(3) 0.009(2) 0.009(2) 0.007(2) C28 0.014(3) 0.021(3) 0.030(3) 0.006(2) 0.009(2) 0.007(2) C29 0.017(3) 0.020(3) 0.033(3) 0.006(2) 0.007(2) 0.004(2) C30 0.021(3) 0.013(2) 0.035(3) 0.0082(19) 0.009(2) 0.003(2) C31 0.022(3) 0.021(3) 0.084(5) -0.005(3) -0.004(3) 0.014(2) C32 0.049(4) 0.034(3) 0.043(4) 0.004(3) 0.009(3) 0.018(3) C33 0.014(3) 0.018(2) 0.033(3) 0.007(2) 0.009(2) 0.006(2) C34 0.015(3) 0.014(2) 0.037(3) 0.004(2) 0.009(2) 0.004(2) C35 0.013(2) 0.009(2) 0.038(3) 0.0070(19) 0.009(2) 0.0032(19) C36 0.013(2) 0.013(2) 0.033(3) 0.0055(19) 0.007(2) 0.0012(19) C37 0.013(3) 0.014(2) 0.031(3) 0.0048(19) 0.0092(19) 0.0037(19) C38 0.006(2) 0.015(2) 0.037(3) 0.0075(19) 0.0060(19) 0.0039(18) C39 0.012(2) 0.015(2) 0.030(3) 0.0039(19) 0.0060(19) 0.0055(19) C40 0.011(2) 0.014(2) 0.032(3) 0.0052(19) 0.0090(19) 0.0035(19) C41 0.010(2) 0.013(2) 0.037(3) 0.0066(19) 0.007(2) 0.0017(19) C42 0.011(2) 0.016(2) 0.037(3) 0.0113(19) 0.010(2) 0.0048(19) C43 0.015(3) 0.017(3) 0.054(4) 0.004(2) 0.010(2) 0.003(2) C44 0.012(3) 0.029(3) 0.053(4) 0.018(2) 0.015(2) 0.008(2) C45 0.009(2) 0.023(3) 0.042(3) 0.006(2) 0.008(2) 0.004(2) C46 0.011(3) 0.018(3) 0.055(4) 0.012(2) 0.012(2) 0.007(2) C47 0.012(3) 0.023(3) 0.047(3) 0.014(2) 0.010(2) 0.006(2) C48 0.012(3) 0.030(3) 0.040(3) 0.008(2) 0.008(2) 0.005(2) C49 0.033(3) 0.031(3) 0.045(4) -0.002(3) 0.004(3) 0.006(3) C50 0.031(3) 0.028(3) 0.056(4) 0.009(3) 0.014(3) 0.008(3) C51 0.019(3) 0.024(3) 0.049(3) 0.012(2) 0.017(2) 0.009(2) C52 0.016(3) 0.028(3) 0.039(3) 0.005(2) 0.007(2) 0.009(2) C53 0.018(3) 0.020(3) 0.049(3) 0.007(2) 0.013(2) 0.008(2) C54 0.034(3) 0.041(3) 0.043(3) 0.015(3) 0.013(3) 0.015(3) C55 0.048(5) 0.100(6) 0.061(5) 0.039(4) 0.010(4) 0.012(4) N1 0.028(3) 0.028(3) 0.061(4) 0.003(3) 0.021(2) 0.005(2) N2 0.022(3) 0.040(3) 0.046(3) 0.009(2) 0.010(2) 0.007(2) N3 0.006(2) 0.038(3) 0.056(3) 0.018(2) 0.008(2) 0.006(2) N4 0.072(5) 0.050(4) 0.050(4) 0.004(3) 0.000(3) 0.004(3) N5 0.021(3) 0.030(3) 0.056(3) 0.016(2) 0.019(2) 0.011(2) N6 0.023(3) 0.026(2) 0.050(3) 0.008(2) 0.006(2) 0.013(2) O1 0.036(2) 0.032(2) 0.050(2) 0.0062(16) 0.0240(18) 0.0189(18) O2 0.049(3) 0.030(2) 0.062(3) 0.0146(18) 0.028(2) 0.0126(19) O3 0.020(2) 0.0185(18) 0.056(2) 0.0079(15) 0.0148(16) 0.0088(15) O4 0.035(2) 0.0168(18) 0.066(3) 0.0164(16) 0.0215(19) 0.0100(16) O5 0.033(2) 0.0176(19) 0.051(2) 0.0021(16) 0.0135(17) 0.0056(16) O6 0.065(3) 0.033(2) 0.046(2) 0.0183(18) 0.021(2) 0.025(2) O7 0.0215(19) 0.0203(18) 0.032(2) 0.0099(14) 0.0106(15) 0.0015(14) O8 0.025(2) 0.0182(18) 0.037(2) 0.0095(14) 0.0042(15) -0.0030(15) O9 0.021(2) 0.0183(18) 0.038(2) 0.0059(14) 0.0086(15) 0.0014(15) O10 0.0094(18) 0.0255(19) 0.056(2) 0.0088(16) 0.0070(15) 0.0016(14) O11 0.0135(19) 0.0239(19) 0.064(3) 0.0036(16) 0.0060(16) 0.0078(15) O12 0.0191(19) 0.0143(17) 0.046(2) 0.0032(14) 0.0032(15) 0.0021(14) O13 0.030(2) 0.031(2) 0.067(3) -0.007(2) 0.021(2) -0.0034(18) O14 0.067(3) 0.030(2) 0.082(3) 0.024(2) 0.028(3) 0.013(2) O15 0.060(3) 0.050(3) 0.049(3) 0.015(2) 0.007(2) 0.013(2) O16 0.033(2) 0.029(2) 0.057(3) -0.0065(18) 0.0103(19) 0.0037(18) O17 0.028(2) 0.032(2) 0.077(3) 0.027(2) 0.010(2) 0.0053(18) O18 0.028(2) 0.062(3) 0.048(3) 0.020(2) 0.0135(19) 0.017(2) O19 0.094(4) 0.067(3) 0.054(3) 0.016(3) -0.006(3) 0.012(3) O20 0.119(5) 0.048(3) 0.073(4) -0.001(3) -0.015(3) -0.006(3) O21 0.033(2) 0.035(2) 0.074(3) 0.024(2) 0.019(2) 0.010(2) O22 0.027(2) 0.046(2) 0.045(2) 0.0169(19) 0.0165(18) 0.0114(18) O23 0.038(3) 0.033(2) 0.052(3) 0.0009(18) 0.0113(19) 0.0131(18) O24 0.036(3) 0.035(2) 0.069(3) 0.024(2) 0.014(2) 0.0166(19) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C55 1.752(9) . ? Cl2 C55 1.773(8) . ? Cl3 C55 1.707(8) . ? Cl1B C55 1.485(15) . ? Cl2B C55 1.83(2) . ? Cl3B C55 1.74(2) . ? C1 O1 1.374(5) . ? C1 C6 1.378(7) . ? C1 C2 1.391(7) . ? C2 O2 1.361(6) . ? C2 C3 1.369(6) . ? C3 C4 1.399(7) . ? C3 H3 0.9500 . ? C4 C5 1.405(6) . ? C4 C33 1.535(6) . ? C5 C6 1.389(6) . ? C5 H5 0.9500 . ? C6 O3 1.384(6) . ? C7 O2 1.436(7) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 O3 1.466(6) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C10 1.352(7) . ? C9 C14 1.368(7) . ? C9 O4 1.391(6) . ? C10 O5 1.381(5) . ? C10 C11 1.386(6) . ? C11 C12 1.392(6) . ? C11 H11 0.9500 . ? C12 C13 1.382(7) . ? C12 C35 1.538(6) . ? C13 C14 1.401(7) . ? C13 H13 0.9500 . ? C14 O6 1.360(6) . ? C15 O5 1.421(6) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 O6 1.414(6) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 O7 1.348(6) . ? C17 C22 1.389(7) . ? C17 C18 1.391(6) . ? C18 O8 1.374(6) . ? C18 C19 1.375(7) . ? C19 C20 1.401(6) . ? C19 H19 0.9500 . ? C20 C21 1.408(6) . ? C20 C37 1.517(7) . ? C21 C22 1.378(7) . ? C21 H21 0.9500 . ? C22 O9 1.381(5) . ? C23 O8 1.426(5) . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 O9 1.433(6) . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 O10 1.365(6) . ? C25 C26 1.380(6) . ? C25 C30 1.381(7) . ? C26 C27 1.381(7) . ? C26 O11 1.385(6) . ? C27 C28 1.405(7) . ? C27 H27 0.9500 . ? C28 C29 1.390(6) . ? C28 C40 1.537(6) . ? C29 C30 1.387(7) . ? C29 H29 0.9500 . ? C30 O12 1.394(5) . ? C31 O11 1.423(6) . ? C31 H31A 0.9800 . ? C31 H31B 0.9800 . ? C31 H31C 0.9800 . ? C32 O12 1.438(6) . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? C33 C38 1.515(7) . ? C33 C34 1.537(6) . ? C33 C39 1.554(6) . ? C34 C35 1.544(6) . ? C34 H34A 0.9900 . ? C34 H34B 0.9900 . ? C35 C36 1.515(7) . ? C35 C42 1.528(6) . ? C36 C37 1.545(6) . ? C36 H36A 0.9900 . ? C36 H36B 0.9900 . ? C37 C41 1.540(6) . ? C37 C38 1.549(6) . ? C38 H38A 0.9900 . ? C38 H38B 0.9900 . ? C39 C40 1.540(6) . ? C39 H39A 0.9900 . ? C39 H39B 0.9900 . ? C40 C41 1.541(7) . ? C40 C42 1.546(6) . ? C41 H41A 0.9900 . ? C41 H41B 0.9900 . ? C42 H42A 0.9900 . ? C42 H42B 0.9900 . ? C43 C48 1.356(8) . ? C43 C44 1.365(7) . ? C43 N1 1.484(7) . ? C44 C45 1.387(7) . ? C44 H44 0.9500 . ? C45 C46 1.389(7) . ? C45 N2 1.458(7) . ? C46 C47 1.377(7) . ? C46 H46 0.9500 . ? C47 C48 1.377(7) . ? C47 N3 1.461(7) . ? C48 H48 0.9500 . ? C49 C50 1.369(8) . ? C49 C54 1.380(8) . ? C49 N4 1.457(8) . ? C50 C51 1.371(8) . ? C50 H50 0.9500 . ? C51 C52 1.395(7) . ? C51 N5 1.454(7) . ? C52 C53 1.375(8) . ? C52 H52 0.9500 . ? C53 C54 1.367(7) . ? C53 N6 1.477(7) . ? C54 H54 0.9500 . ? C55 H55 1.0000 . ? N1 O14 1.207(7) . ? N1 O13 1.218(6) . ? N2 O15 1.223(6) . ? N2 O16 1.226(6) . ? N3 O18 1.219(5) . ? N3 O17 1.234(5) . ? N4 O19 1.216(7) . ? N4 O20 1.243(7) . ? N5 O22 1.217(6) . ? N5 O21 1.231(5) . ? N6 O24 1.218(6) . ? N6 O23 1.220(5) . ? O1 H1 0.8400 . ? O4 H4 0.8400 . ? O7 H7 0.8400 . ? O10 H10 0.8400 . ? 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 C6 121.4(4) . . ? O1 C1 C2 119.9(5) . . ? C6 C1 C2 118.7(4) . . ? O2 C2 C3 125.6(5) . . ? O2 C2 C1 112.6(4) . . ? C3 C2 C1 121.8(5) . . ? C2 C3 C4 119.9(4) . . ? C2 C3 H3 120.0 . . ? C4 C3 H3 120.0 . . ? C3 C4 C5 118.7(4) . . ? C3 C4 C33 122.1(4) . . ? C5 C4 C33 119.2(4) . . ? C6 C5 C4 120.1(5) . . ? C6 C5 H5 119.9 . . ? C4 C5 H5 119.9 . . ? C1 C6 O3 115.1(4) . . ? C1 C6 C5 120.7(4) . . ? O3 C6 C5 124.2(5) . . ? O2 C7 H7A 109.5 . . ? O2 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? O2 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? O3 C8 H8A 109.5 . . ? O3 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? O3 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C10 C9 C14 120.1(5) . . ? C10 C9 O4 120.3(4) . . ? C14 C9 O4 119.6(5) . . ? C9 C10 O5 113.9(4) . . ? C9 C10 C11 120.4(4) . . ? O5 C10 C11 125.7(5) . . ? C10 C11 C12 121.3(5) . . ? C10 C11 H11 119.3 . . ? C12 C11 H11 119.3 . . ? C13 C12 C11 117.2(5) . . ? C13 C12 C35 120.6(4) . . ? C11 C12 C35 122.2(5) . . ? C12 C13 C14 121.0(4) . . ? C12 C13 H13 119.5 . . ? C14 C13 H13 119.5 . . ? O6 C14 C9 115.4(5) . . ? O6 C14 C13 124.8(4) . . ? C9 C14 C13 119.8(5) . . ? O5 C15 H15A 109.5 . . ? O5 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? O5 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? O6 C16 H16A 109.5 . . ? O6 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? O6 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? O7 C17 C22 118.2(4) . . ? O7 C17 C18 123.9(4) . . ? C22 C17 C18 117.8(5) . . ? O8 C18 C19 125.3(4) . . ? O8 C18 C17 112.8(4) . . ? C19 C18 C17 121.9(4) . . ? C18 C19 C20 120.2(4) . . ? C18 C19 H19 119.9 . . ? C20 C19 H19 119.9 . . ? C19 C20 C21 118.2(5) . . ? C19 C20 C37 121.6(4) . . ? C21 C20 C37 120.2(4) . . ? C22 C21 C20 120.3(5) . . ? C22 C21 H21 119.8 . . ? C20 C21 H21 119.8 . . ? C21 C22 O9 123.9(4) . . ? C21 C22 C17 121.5(4) . . ? O9 C22 C17 114.6(4) . . ? O8 C23 H23A 109.5 . . ? O8 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? O8 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? O9 C24 H24A 109.5 . . ? O9 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? O9 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? O10 C25 C26 121.8(4) . . ? O10 C25 C30 120.1(4) . . ? C26 C25 C30 118.1(4) . . ? C25 C26 C27 122.1(4) . . ? C25 C26 O11 113.0(4) . . ? C27 C26 O11 124.9(4) . . ? C26 C27 C28 119.9(4) . . ? C26 C27 H27 120.1 . . ? C28 C27 H27 120.1 . . ? C29 C28 C27 117.8(4) . . ? C29 C28 C40 120.5(4) . . ? C27 C28 C40 121.6(4) . . ? C30 C29 C28 121.2(5) . . ? C30 C29 H29 119.4 . . ? C28 C29 H29 119.4 . . ? C25 C30 C29 120.8(4) . . ? C25 C30 O12 120.9(4) . . ? C29 C30 O12 118.2(4) . . ? O11 C31 H31A 109.5 . . ? O11 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? O11 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? O12 C32 H32A 109.5 . . ? O12 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? O12 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C38 C33 C4 111.2(4) . . ? C38 C33 C34 109.1(4) . . ? C4 C33 C34 111.8(4) . . ? C38 C33 C39 109.3(4) . . ? C4 C33 C39 108.5(4) . . ? C34 C33 C39 106.8(4) . . ? C33 C34 C35 111.9(4) . . ? C33 C34 H34A 109.2 . . ? C35 C34 H34A 109.2 . . ? C33 C34 H34B 109.2 . . ? C35 C34 H34B 109.2 . . ? H34A C34 H34B 107.9 . . ? C36 C35 C42 108.9(4) . . ? C36 C35 C12 110.7(4) . . ? C42 C35 C12 110.8(4) . . ? C36 C35 C34 107.4(4) . . ? C42 C35 C34 108.9(4) . . ? C12 C35 C34 110.0(4) . . ? C35 C36 C37 113.1(3) . . ? C35 C36 H36A 109.0 . . ? C37 C36 H36A 109.0 . . ? C35 C36 H36B 109.0 . . ? C37 C36 H36B 109.0 . . ? H36A C36 H36B 107.8 . . ? C20 C37 C41 111.7(4) . . ? C20 C37 C36 111.3(3) . . ? C41 C37 C36 107.9(4) . . ? C20 C37 C38 110.5(4) . . ? C41 C37 C38 108.0(4) . . ? C36 C37 C38 107.2(4) . . ? C33 C38 C37 111.8(4) . . ? C33 C38 H38A 109.2 . . ? C37 C38 H38A 109.2 . . ? C33 C38 H38B 109.2 . . ? C37 C38 H38B 109.2 . . ? H38A C38 H38B 107.9 . . ? C40 C39 C33 111.4(4) . . ? C40 C39 H39A 109.4 . . ? C33 C39 H39A 109.4 . . ? C40 C39 H39B 109.4 . . ? C33 C39 H39B 109.4 . . ? H39A C39 H39B 108.0 . . ? C28 C40 C39 110.2(4) . . ? C28 C40 C41 109.2(4) . . ? C39 C40 C41 108.0(4) . . ? C28 C40 C42 111.9(4) . . ? C39 C40 C42 108.8(4) . . ? C41 C40 C42 108.7(3) . . ? C37 C41 C40 112.0(4) . . ? C37 C41 H41A 109.2 . . ? C40 C41 H41A 109.2 . . ? C37 C41 H41B 109.2 . . ? C40 C41 H41B 109.2 . . ? H41A C41 H41B 107.9 . . ? C35 C42 C40 110.9(4) . . ? C35 C42 H42A 109.5 . . ? C40 C42 H42A 109.5 . . ? C35 C42 H42B 109.5 . . ? C40 C42 H42B 109.5 . . ? H42A C42 H42B 108.0 . . ? C48 C43 C44 123.8(5) . . ? C48 C43 N1 117.7(5) . . ? C44 C43 N1 118.4(5) . . ? C43 C44 C45 117.4(5) . . ? C43 C44 H44 121.3 . . ? C45 C44 H44 121.3 . . ? C44 C45 C46 121.6(5) . . ? C44 C45 N2 120.7(5) . . ? C46 C45 N2 117.6(5) . . ? C47 C46 C45 117.1(5) . . ? C47 C46 H46 121.4 . . ? C45 C46 H46 121.4 . . ? C48 C47 C46 122.9(5) . . ? C48 C47 N3 118.6(5) . . ? C46 C47 N3 118.5(5) . . ? C43 C48 C47 117.1(5) . . ? C43 C48 H48 121.4 . . ? C47 C48 H48 121.4 . . ? C50 C49 C54 123.2(5) . . ? C50 C49 N4 117.4(5) . . ? C54 C49 N4 119.3(6) . . ? C49 C50 C51 117.0(5) . . ? C49 C50 H50 121.5 . . ? C51 C50 H50 121.5 . . ? C50 C51 C52 122.7(5) . . ? C50 C51 N5 119.0(5) . . ? C52 C51 N5 118.3(5) . . ? C53 C52 C51 116.9(5) . . ? C53 C52 H52 121.6 . . ? C51 C52 H52 121.6 . . ? C54 C53 C52 122.9(5) . . ? C54 C53 N6 118.9(5) . . ? C52 C53 N6 118.1(5) . . ? C53 C54 C49 117.2(5) . . ? C53 C54 H54 121.4 . . ? C49 C54 H54 121.4 . . ? Cl1B C55 Cl3 140.1(9) . . ? Cl1B C55 Cl3B 131.7(15) . . ? Cl3 C55 Cl3B 41.4(15) . . ? Cl1B C55 Cl1 47.2(8) . . ? Cl3 C55 Cl1 110.3(5) . . ? Cl3B C55 Cl1 142.4(9) . . ? Cl1B C55 Cl2 63.0(9) . . ? Cl3 C55 Cl2 112.5(5) . . ? Cl3B C55 Cl2 75.3(15) . . ? Cl1 C55 Cl2 108.3(5) . . ? Cl1B C55 Cl2B 97.5(13) . . ? Cl3 C55 Cl2B 63.0(9) . . ? Cl3B C55 Cl2B 104.0(16) . . ? Cl1 C55 Cl2B 51.4(9) . . ? Cl2 C55 Cl2B 145.3(9) . . ? Cl1B C55 H55 110.2 . . ? Cl3 C55 H55 108.5 . . ? Cl3B C55 H55 105.2 . . ? Cl1 C55 H55 108.5 . . ? Cl2 C55 H55 108.5 . . ? Cl2B C55 H55 105.1 . . ? O14 N1 O13 124.8(5) . . ? O14 N1 C43 118.1(5) . . ? O13 N1 C43 117.0(5) . . ? O15 N2 O16 125.2(5) . . ? O15 N2 C45 116.1(5) . . ? O16 N2 C45 118.8(5) . . ? O18 N3 O17 125.2(5) . . ? O18 N3 C47 117.6(5) . . ? O17 N3 C47 117.2(5) . . ? O19 N4 O20 123.3(6) . . ? O19 N4 C49 118.3(6) . . ? O20 N4 C49 118.4(6) . . ? O22 N5 O21 124.3(5) . . ? O22 N5 C51 118.5(5) . . ? O21 N5 C51 117.2(5) . . ? O24 N6 O23 125.1(5) . . ? O24 N6 C53 117.2(4) . . ? O23 N6 C53 117.7(5) . . ? C1 O1 H1 109.5 . . ? C2 O2 C7 116.4(4) . . ? C6 O3 C8 116.7(4) . . ? C9 O4 H4 109.5 . . ? C10 O5 C15 119.3(4) . . ? C14 O6 C16 117.7(4) . . ? C17 O7 H7 109.5 . . ? C18 O8 C23 118.8(4) . . ? C22 O9 C24 117.4(4) . . ? C25 O10 H10 109.5 . . ? C26 O11 C31 118.0(4) . . ? C30 O12 C32 114.7(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 O2 -0.7(7) . . . . ? C6 C1 C2 O2 177.6(5) . . . . ? O1 C1 C2 C3 178.8(5) . . . . ? C6 C1 C2 C3 -2.9(8) . . . . ? O2 C2 C3 C4 -179.8(5) . . . . ? C1 C2 C3 C4 0.8(8) . . . . ? C2 C3 C4 C5 0.6(7) . . . . ? C2 C3 C4 C33 -177.6(5) . . . . ? C3 C4 C5 C6 0.2(7) . . . . ? C33 C4 C5 C6 178.4(4) . . . . ? O1 C1 C6 O3 2.1(7) . . . . ? C2 C1 C6 O3 -176.3(4) . . . . ? O1 C1 C6 C5 -178.1(5) . . . . ? C2 C1 C6 C5 3.6(8) . . . . ? C4 C5 C6 C1 -2.3(7) . . . . ? C4 C5 C6 O3 177.6(4) . . . . ? C14 C9 C10 O5 -176.3(4) . . . . ? O4 C9 C10 O5 4.0(7) . . . . ? C14 C9 C10 C11 3.7(7) . . . . ? O4 C9 C10 C11 -176.0(4) . . . . ? C9 C10 C11 C12 -2.1(7) . . . . ? O5 C10 C11 C12 177.8(4) . . . . ? C10 C11 C12 C13 -1.8(7) . . . . ? C10 C11 C12 C35 177.0(4) . . . . ? C11 C12 C13 C14 4.1(7) . . . . ? C35 C12 C13 C14 -174.6(4) . . . . ? C10 C9 C14 O6 177.6(5) . . . . ? O4 C9 C14 O6 -2.7(7) . . . . ? C10 C9 C14 C13 -1.3(8) . . . . ? O4 C9 C14 C13 178.4(4) . . . . ? C12 C13 C14 O6 178.4(5) . . . . ? C12 C13 C14 C9 -2.7(7) . . . . ? O7 C17 C18 O8 -1.5(6) . . . . ? C22 C17 C18 O8 176.1(4) . . . . ? O7 C17 C18 C19 178.7(4) . . . . ? C22 C17 C18 C19 -3.6(7) . . . . ? O8 C18 C19 C20 -178.3(4) . . . . ? C17 C18 C19 C20 1.4(7) . . . . ? C18 C19 C20 C21 1.4(6) . . . . ? C18 C19 C20 C37 -178.7(4) . . . . ? C19 C20 C21 C22 -1.9(6) . . . . ? C37 C20 C21 C22 178.1(4) . . . . ? C20 C21 C22 O9 180.0(4) . . . . ? C20 C21 C22 C17 -0.4(7) . . . . ? O7 C17 C22 C21 -179.1(4) . . . . ? C18 C17 C22 C21 3.1(7) . . . . ? O7 C17 C22 O9 0.6(6) . . . . ? C18 C17 C22 O9 -177.2(4) . . . . ? O10 C25 C26 C27 179.1(5) . . . . ? C30 C25 C26 C27 -0.3(8) . . . . ? O10 C25 C26 O11 -0.3(7) . . . . ? C30 C25 C26 O11 -179.8(4) . . . . ? C25 C26 C27 C28 -0.7(8) . . . . ? O11 C26 C27 C28 178.6(5) . . . . ? C26 C27 C28 C29 0.8(7) . . . . ? C26 C27 C28 C40 -177.1(5) . . . . ? C27 C28 C29 C30 0.1(7) . . . . ? C40 C28 C29 C30 178.0(4) . . . . ? O10 C25 C30 C29 -178.2(4) . . . . ? C26 C25 C30 C29 1.3(7) . . . . ? O10 C25 C30 O12 -0.8(7) . . . . ? C26 C25 C30 O12 178.7(4) . . . . ? C28 C29 C30 C25 -1.2(8) . . . . ? C28 C29 C30 O12 -178.6(4) . . . . ? C3 C4 C33 C38 -130.0(5) . . . . ? C5 C4 C33 C38 51.8(5) . . . . ? C3 C4 C33 C34 -7.8(6) . . . . ? C5 C4 C33 C34 174.0(4) . . . . ? C3 C4 C33 C39 109.7(5) . . . . ? C5 C4 C33 C39 -68.5(5) . . . . ? C38 C33 C34 C35 -58.4(5) . . . . ? C4 C33 C34 C35 178.2(4) . . . . ? C39 C33 C34 C35 59.6(5) . . . . ? C13 C12 C35 C36 167.4(4) . . . . ? C11 C12 C35 C36 -11.3(6) . . . . ? C13 C12 C35 C42 -71.7(5) . . . . ? C11 C12 C35 C42 109.6(5) . . . . ? C13 C12 C35 C34 48.8(6) . . . . ? C11 C12 C35 C34 -129.9(5) . . . . ? C33 C34 C35 C36 57.9(5) . . . . ? C33 C34 C35 C42 -59.9(5) . . . . ? C33 C34 C35 C12 178.5(4) . . . . ? C42 C35 C36 C37 58.7(5) . . . . ? C12 C35 C36 C37 -179.3(3) . . . . ? C34 C35 C36 C37 -59.1(5) . . . . ? C19 C20 C37 C41 41.7(5) . . . . ? C21 C20 C37 C41 -138.3(4) . . . . ? C19 C20 C37 C36 162.5(4) . . . . ? C21 C20 C37 C36 -17.6(6) . . . . ? C19 C20 C37 C38 -78.5(5) . . . . ? C21 C20 C37 C38 101.4(5) . . . . ? C35 C36 C37 C20 180.0(4) . . . . ? C35 C36 C37 C41 -57.1(5) . . . . ? C35 C36 C37 C38 59.1(5) . . . . ? C4 C33 C38 C37 -177.9(4) . . . . ? C34 C33 C38 C37 58.3(5) . . . . ? C39 C33 C38 C37 -58.1(5) . . . . ? C20 C37 C38 C33 -179.2(4) . . . . ? C41 C37 C38 C33 58.3(5) . . . . ? C36 C37 C38 C33 -57.7(5) . . . . ? C38 C33 C39 C40 58.1(5) . . . . ? C4 C33 C39 C40 179.5(4) . . . . ? C34 C33 C39 C40 -59.8(5) . . . . ? C29 C28 C40 C39 43.3(6) . . . . ? C27 C28 C40 C39 -138.9(5) . . . . ? C29 C28 C40 C41 -75.2(5) . . . . ? C27 C28 C40 C41 102.6(5) . . . . ? C29 C28 C40 C42 164.4(4) . . . . ? C27 C28 C40 C42 -17.7(6) . . . . ? C33 C39 C40 C28 -177.1(4) . . . . ? C33 C39 C40 C41 -58.0(5) . . . . ? C33 C39 C40 C42 59.8(5) . . . . ? C20 C37 C41 C40 179.2(3) . . . . ? C36 C37 C41 C40 56.6(4) . . . . ? C38 C37 C41 C40 -59.1(5) . . . . ? C28 C40 C41 C37 179.2(3) . . . . ? C39 C40 C41 C37 59.4(5) . . . . ? C42 C40 C41 C37 -58.4(5) . . . . ? C36 C35 C42 C40 -58.8(5) . . . . ? C12 C35 C42 C40 179.2(4) . . . . ? C34 C35 C42 C40 58.0(5) . . . . ? C28 C40 C42 C35 179.6(4) . . . . ? C39 C40 C42 C35 -58.4(5) . . . . ? C41 C40 C42 C35 58.9(5) . . . . ? C48 C43 C44 C45 -1.6(7) . . . . ? N1 C43 C44 C45 -179.3(4) . . . . ? C43 C44 C45 C46 1.7(7) . . . . ? C43 C44 C45 N2 178.8(4) . . . . ? C44 C45 C46 C47 -1.6(7) . . . . ? N2 C45 C46 C47 -178.7(4) . . . . ? C45 C46 C47 C48 1.3(7) . . . . ? C45 C46 C47 N3 -179.3(4) . . . . ? C44 C43 C48 C47 1.3(7) . . . . ? N1 C43 C48 C47 179.0(4) . . . . ? C46 C47 C48 C43 -1.1(7) . . . . ? N3 C47 C48 C43 179.4(4) . . . . ? C54 C49 C50 C51 2.7(8) . . . . ? N4 C49 C50 C51 -177.8(5) . . . . ? C49 C50 C51 C52 -0.2(8) . . . . ? C49 C50 C51 N5 179.1(5) . . . . ? C50 C51 C52 C53 -1.4(7) . . . . ? N5 C51 C52 C53 179.3(4) . . . . ? C51 C52 C53 C54 0.7(7) . . . . ? C51 C52 C53 N6 -179.0(4) . . . . ? C52 C53 C54 C49 1.5(8) . . . . ? N6 C53 C54 C49 -178.8(5) . . . . ? C50 C49 C54 C53 -3.3(8) . . . . ? N4 C49 C54 C53 177.1(5) . . . . ? C48 C43 N1 O14 169.2(5) . . . . ? C44 C43 N1 O14 -12.9(7) . . . . ? C48 C43 N1 O13 -9.2(7) . . . . ? C44 C43 N1 O13 168.7(4) . . . . ? C44 C45 N2 O15 6.9(7) . . . . ? C46 C45 N2 O15 -175.9(5) . . . . ? C44 C45 N2 O16 -174.4(5) . . . . ? C46 C45 N2 O16 2.8(6) . . . . ? C48 C47 N3 O18 -11.8(6) . . . . ? C46 C47 N3 O18 168.7(4) . . . . ? C48 C47 N3 O17 169.3(4) . . . . ? C46 C47 N3 O17 -10.2(6) . . . . ? C50 C49 N4 O19 177.0(6) . . . . ? C54 C49 N4 O19 -3.4(9) . . . . ? C50 C49 N4 O20 -1.5(9) . . . . ? C54 C49 N4 O20 178.1(6) . . . . ? C50 C51 N5 O22 176.4(5) . . . . ? C52 C51 N5 O22 -4.2(6) . . . . ? C50 C51 N5 O21 -4.5(7) . . . . ? C52 C51 N5 O21 174.9(4) . . . . ? C54 C53 N6 O24 -17.7(7) . . . . ? C52 C53 N6 O24 161.9(4) . . . . ? C54 C53 N6 O23 160.8(5) . . . . ? C52 C53 N6 O23 -19.5(6) . . . . ? C3 C2 O2 C7 1.3(8) . . . . ? C1 C2 O2 C7 -179.2(5) . . . . ? C1 C6 O3 C8 -176.1(5) . . . . ? C5 C6 O3 C8 4.1(7) . . . . ? C9 C10 O5 C15 -179.0(4) . . . . ? C11 C10 O5 C15 1.0(7) . . . . ? C9 C14 O6 C16 179.4(5) . . . . ? C13 C14 O6 C16 -1.7(8) . . . . ? C19 C18 O8 C23 0.8(7) . . . . ? C17 C18 O8 C23 -179.0(4) . . . . ? C21 C22 O9 C24 -6.6(6) . . . . ? C17 C22 O9 C24 173.7(4) . . . . ? C25 C26 O11 C31 -174.0(5) . . . . ? C27 C26 O11 C31 6.6(8) . . . . ? C25 C30 O12 C32 63.8(6) . . . . ? C29 C30 O12 C32 -118.7(5) . . . . ? 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 O1 H1 O1 0.84 2.22 2.945(7) 145.0 2_666 O4 H4 O13 0.84 2.52 3.259(6) 147.1 1_566 O7 H7 O12 0.84 1.95 2.683(5) 144.9 2_567 O10 H10 O3 0.84 2.13 2.874(5) 147.3 1_455 _diffrn_measured_fraction_theta_max 0.847 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.957 _refine_diff_density_max 0.701 _refine_diff_density_min -0.587 _refine_diff_density_rms 0.099