# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Liuzhu Gong' _publ_contact_author_email GONGLZ@USTC.EDU.CN _publ_section_title ; Asymmetric Organocatalytic Formal Double-Arylation of Azomethines for the Synthesis of Highly Enantiomerically Enriched Isoindolines ; loop_ _publ_author_name 'Liuzhu Gong' 'Xiao-Hua Chen' 'Chao Wang' # Attachment '080927-cu.cif.txt' data_080927-cu _database_code_depnum_ccdc_archive 'CCDC 704878' #TrackingRef '080927-cu.cif.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C48 H42 Cl4 N2 O12' _chemical_formula_weight 980.64 _chemical_absolute_configuration ad loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 8.314(5) _cell_length_b 22.630(5) _cell_length_c 12.582(5) _cell_angle_alpha 90.000(5) _cell_angle_beta 94.055(5) _cell_angle_gamma 90.000(5) _cell_volume 2361.3(18) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 23144 _cell_measurement_theta_min 1.9465 _cell_measurement_theta_max 62.6295 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.379 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1016 _exptl_absorpt_coefficient_mu 2.820 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4137 _exptl_absorpt_correction_T_max 0.5509 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.24 (release 21-04-2008 CrysAlis171 .NET) (compiled Apr 21 2008,18:23:10) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Enhance Ultra (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'Gemini S Ultra, Oxford Diffraction' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 15.9149 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 29413 _diffrn_reflns_av_R_equivalents 0.0201 _diffrn_reflns_av_sigmaI/netI 0.0149 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.52 _diffrn_reflns_theta_max 62.78 _reflns_number_total 7332 _reflns_number_gt 6900 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlisPro (Oxford Diffraction Ltd.)' _computing_cell_refinement 'CrysAlisPro (Oxford Diffraction Ltd.)' _computing_data_reduction 'CrysAlisPro (Oxford Diffraction Ltd.)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 (L. J. Farrugia, 2001)' _computing_publication_material SHELXL-97 _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^)+(0.0688P)^2^+1.9006P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.016(19) _refine_ls_number_reflns 7332 _refine_ls_number_parameters 603 _refine_ls_number_restraints 61 _refine_ls_R_factor_all 0.0594 _refine_ls_R_factor_gt 0.0571 _refine_ls_wR_factor_ref 0.1447 _refine_ls_wR_factor_gt 0.1429 _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_restrained_S_all 1.104 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl2 Cl 0.0688(2) 0.77915(7) 0.37046(13) 0.0981(5) Uani 1 1 d . . . Cl4 Cl 0.6479(2) 0.65887(8) 0.87584(14) 0.1044(5) Uani 1 1 d . . . Cl1 Cl 0.1434(4) 0.90098(8) 0.26706(16) 0.1521(11) Uani 1 1 d . . . Cl3 Cl 0.5372(4) 0.53653(8) 0.78250(17) 0.1486(10) Uani 1 1 d . . . O10 O 0.1700(4) 0.93884(14) 0.9403(3) 0.0722(8) Uani 1 1 d DU . . O2 O 0.3254(4) 0.76237(15) 0.6130(2) 0.0675(8) Uani 1 1 d . . . N1 N 0.4573(5) 0.64942(15) 0.3426(3) 0.0563(8) Uani 1 1 d D . . O6 O 0.5949(5) 0.50677(17) 0.4283(3) 0.0866(10) Uani 1 1 d DU . . O9 O 0.1017(4) 0.89618(14) 0.7817(3) 0.0679(8) Uani 1 1 d . . . N2 N 0.2838(4) 0.79707(15) 0.8425(3) 0.0524(8) Uani 1 1 d D . . O12 O 0.4954(4) 0.90240(17) 0.8498(3) 0.0799(10) Uani 1 1 d . . . O8 O 0.3795(4) 0.66882(16) 1.1018(3) 0.0760(9) Uani 1 1 d . . . O4 O 0.2626(5) 0.5445(2) 0.4946(3) 0.0970(11) Uani 1 1 d DU . . C32 C 0.2868(5) 0.7088(2) 1.0764(3) 0.0553(10) Uani 1 1 d . . . C34 C 0.2352(5) 0.81635(18) 1.0149(3) 0.0501(9) Uani 1 1 d . . . H34 H 0.2648 0.8414 1.0767 0.060 Uiso 1 1 calc R . . C28 C 0.1146(5) 0.7059(2) 1.1030(3) 0.0566(10) Uani 1 1 d . . . O11 O 0.5263(5) 0.8778(2) 1.0194(3) 0.0947(13) Uani 1 1 d . . . C36 C 0.3783(5) 0.75024(17) 0.8972(3) 0.0507(9) Uani 1 1 d . . . H36 H 0.4930 0.7568 0.8879 0.061 Uiso 1 1 calc R . . C12 C 0.3519(5) 0.69131(17) 0.3933(3) 0.0533(9) Uani 1 1 d D . . H12 H 0.2396 0.6814 0.3717 0.064 Uiso 1 1 calc R . . O5 O 0.6640(5) 0.56180(17) 0.2926(4) 0.0945(13) Uani 1 1 d . . . C43 C 0.1687(5) 0.8958(2) 0.8682(4) 0.0564(9) Uani 1 1 d U . . C10 C 0.5039(5) 0.62624(19) 0.5188(3) 0.0539(10) Uani 1 1 d . . . H10 H 0.4804 0.5988 0.5758 0.065 Uiso 1 1 calc R . . C11 C 0.4673(6) 0.59727(18) 0.4084(3) 0.0560(10) Uani 1 1 d . . . C33 C 0.3446(5) 0.76154(18) 1.0184(3) 0.0496(9) Uani 1 1 d . . . H33 H 0.4475 0.7734 1.0551 0.059 Uiso 1 1 calc R . . C29 C 0.0061(5) 0.7506(2) 1.0700(3) 0.0574(10) Uani 1 1 d . . . C37 C 0.3304(6) 0.69033(18) 0.8548(3) 0.0592(11) Uani 1 1 d . . . C35 C 0.2828(5) 0.84752(17) 0.9134(3) 0.0489(9) Uani 1 1 d . . . O7 O -0.0417(4) 0.83553(19) 0.9659(4) 0.0938(13) Uani 1 1 d . . . C4 C 0.6025(5) 0.7427(2) 0.6089(3) 0.0544(10) Uani 1 1 d . . . C8 C 0.4300(5) 0.73023(19) 0.5822(3) 0.0505(9) Uani 1 1 d . . . C5 C 0.7202(5) 0.7031(2) 0.5798(3) 0.0587(10) Uani 1 1 d . . . C22 C 0.5929(6) 0.55465(19) 0.3700(4) 0.0641(12) Uani 1 1 d . . . C13 C 0.3858(6) 0.75379(18) 0.3553(3) 0.0581(11) Uani 1 1 d . . . C6 C 0.8841(6) 0.7186(3) 0.6017(4) 0.0744(14) Uani 1 1 d . . . H6 H 0.9655 0.6934 0.5822 0.089 Uiso 1 1 calc R . . C9 C 0.3834(5) 0.67762(18) 0.5130(3) 0.0509(9) Uani 1 1 d D . . H9 H 0.2822 0.6623 0.5376 0.061 Uiso 1 1 calc R . . C30 C -0.1552(6) 0.7458(3) 1.0931(4) 0.0775(14) Uani 1 1 d . . . H30 H -0.2289 0.7750 1.0713 0.093 Uiso 1 1 calc R . . C46 C 0.4491(5) 0.8780(2) 0.9353(4) 0.0596(11) Uani 1 1 d . . . C18 C 0.5388(7) 0.7701(2) 0.3332(4) 0.0715(13) Uani 1 1 d . . . H18 H 0.6223 0.7431 0.3457 0.086 Uiso 1 1 calc R . . C38 C 0.1697(7) 0.6778(2) 0.8266(4) 0.0728(13) Uani 1 1 d . . . H38 H 0.0918 0.7068 0.8338 0.087 Uiso 1 1 calc R . . C3 C 0.6477(6) 0.7949(3) 0.6609(4) 0.0717(13) Uani 1 1 d . . . H3 H 0.5687 0.8209 0.6808 0.086 Uiso 1 1 calc R . . O1 O 0.7864(5) 0.6134(2) 0.5036(5) 0.126(2) Uani 1 1 d . . . C25 C -0.2041(7) 0.6975(3) 1.1484(5) 0.0860(17) Uani 1 1 d . . . H25 H -0.3121 0.6939 1.1623 0.103 Uiso 1 1 calc R . . C44 C 0.0783(7) 0.9917(2) 0.9098(4) 0.0743(10) Uani 1 1 d DU . . H44A H -0.0259 0.9809 0.8758 0.089 Uiso 1 1 calc R . . H44B H 0.1357 1.0150 0.8600 0.089 Uiso 1 1 calc R . . C7 C 0.6812(6) 0.6459(2) 0.5305(4) 0.0691(12) Uani 1 1 d . . . C40 C 0.2388(13) 0.5798(3) 0.7751(5) 0.109(3) Uani 1 1 d . . . H40 H 0.2076 0.5429 0.7483 0.131 Uiso 1 1 calc R . . C26 C -0.0970(7) 0.6540(3) 1.1839(4) 0.0816(15) Uani 1 1 d . . . H26 H -0.1319 0.6227 1.2241 0.098 Uiso 1 1 calc R . . C41 C 0.3968(12) 0.5913(2) 0.8015(4) 0.095(2) Uani 1 1 d . . . C19 C 0.3078(6) 0.5621(2) 0.4015(4) 0.0615(11) Uani 1 1 d . . . C16 C 0.4530(14) 0.8648(3) 0.2751(5) 0.113(3) Uani 1 1 d . . . H16 H 0.4756 0.9019 0.2478 0.136 Uiso 1 1 calc R . . C47 C 0.6360(7) 0.9420(3) 0.8652(5) 0.0921(18) Uani 1 1 d D . . H47A H 0.6751 0.9513 0.7963 0.110 Uiso 1 1 calc R . . H47B H 0.7216 0.9216 0.9069 0.110 Uiso 1 1 calc R . . C48 C 0.5972(8) 0.9988(2) 0.9210(6) 0.107(2) Uani 1 1 d D . . H48A H 0.6926 1.0227 0.9302 0.160 Uiso 1 1 calc R . . H48B H 0.5588 0.9899 0.9894 0.160 Uiso 1 1 calc R . . H48C H 0.5154 1.0199 0.8788 0.160 Uiso 1 1 calc R . . C31 C 0.0574(5) 0.8030(2) 1.0114(4) 0.0597(10) Uani 1 1 d . . . C1 C 0.9218(7) 0.7711(3) 0.6520(5) 0.0831(16) Uani 1 1 d . . . H1 H 1.0296 0.7814 0.6649 0.100 Uiso 1 1 calc R . . C42 C 0.4454(7) 0.6460(2) 0.8412(4) 0.0734(13) Uani 1 1 d . . . C27 C 0.0621(6) 0.6571(2) 1.1597(4) 0.0696(12) Uani 1 1 d . . . H27 H 0.1338 0.6271 1.1809 0.084 Uiso 1 1 calc R . . C15 C 0.2976(11) 0.8510(2) 0.2966(4) 0.095(2) Uani 1 1 d . . . C17 C 0.5734(10) 0.8250(3) 0.2932(5) 0.0943(19) Uani 1 1 d . . . H17 H 0.6784 0.8346 0.2788 0.113 Uiso 1 1 calc R . . C23 C 0.7037(8) 0.4621(3) 0.3889(5) 0.0952(13) Uani 1 1 d DU . . H23A H 0.8153 0.4739 0.4030 0.114 Uiso 1 1 calc R . . H23B H 0.6826 0.4564 0.3128 0.114 Uiso 1 1 calc R . . C39 C 0.1243(10) 0.6229(3) 0.7882(5) 0.103(2) Uani 1 1 d . . . H39 H 0.0160 0.6149 0.7710 0.123 Uiso 1 1 calc R . . C2 C 0.8066(7) 0.8084(3) 0.6833(5) 0.0860(16) Uani 1 1 d . . . H2 H 0.8356 0.8429 0.7198 0.103 Uiso 1 1 calc R . . C14 C 0.2613(7) 0.7951(2) 0.3394(4) 0.0734(13) Uani 1 1 d . . . C45 C 0.0568(8) 1.0268(3) 1.0104(4) 0.0890(12) Uani 1 1 d DU . . H45A H -0.0052 1.0617 0.9930 0.134 Uiso 1 1 calc R . . H45B H 0.1605 1.0379 1.0426 0.134 Uiso 1 1 calc R . . H45C H 0.0013 1.0031 1.0595 0.134 Uiso 1 1 calc R . . C24 C 0.6700(9) 0.4059(3) 0.4483(6) 0.1011(14) Uani 1 1 d DU . . H24A H 0.7383 0.3749 0.4256 0.152 Uiso 1 1 calc R . . H24B H 0.5591 0.3949 0.4337 0.152 Uiso 1 1 calc R . . H24C H 0.6910 0.4123 0.5235 0.152 Uiso 1 1 calc R . . O3 O 0.2353(5) 0.55210(17) 0.3181(3) 0.0895(11) Uani 1 1 d . . . C20 C 0.1188(8) 0.5085(3) 0.4920(6) 0.1019(14) Uani 1 1 d DU . . H20A H 0.0552 0.5140 0.4251 0.122 Uiso 1 1 calc R . . H20B H 0.0534 0.5194 0.5498 0.122 Uiso 1 1 calc R . . C21 C 0.1722(10) 0.4452(3) 0.5039(7) 0.1218(16) Uani 1 1 d DU . . H21A H 0.0793 0.4199 0.5026 0.183 Uiso 1 1 calc R . . H21B H 0.2349 0.4403 0.5704 0.183 Uiso 1 1 calc R . . H21C H 0.2366 0.4348 0.4462 0.183 Uiso 1 1 calc R . . H4 H 0.411(6) 0.639(2) 0.279(3) 0.075(15) Uiso 1 1 d D . . H28 H 0.319(5) 0.804(2) 0.782(3) 0.057(13) Uiso 1 1 d 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 0.1005(10) 0.0987(11) 0.0944(10) -0.0121(8) 0.0019(8) 0.0346(9) Cl4 0.1025(11) 0.1003(11) 0.1107(11) -0.0020(9) 0.0094(9) 0.0438(9) Cl1 0.271(3) 0.0852(11) 0.0994(12) 0.0047(9) 0.0079(15) 0.0874(16) Cl3 0.261(3) 0.0729(10) 0.1119(13) -0.0095(9) 0.0116(15) 0.0728(14) O10 0.081(2) 0.0608(16) 0.073(2) -0.0032(12) -0.0069(16) 0.0000(13) O2 0.0602(18) 0.079(2) 0.0640(18) -0.0175(16) 0.0105(14) 0.0046(16) N1 0.076(2) 0.0445(18) 0.0494(19) 0.0017(15) 0.0101(17) -0.0044(17) O6 0.090(2) 0.0803(18) 0.092(3) 0.0104(19) 0.028(2) -0.0065(17) O9 0.071(2) 0.0630(19) 0.068(2) 0.0075(15) -0.0101(16) -0.0031(15) N2 0.066(2) 0.0470(17) 0.0447(18) -0.0003(14) 0.0105(16) -0.0045(16) O12 0.071(2) 0.095(3) 0.073(2) 0.0191(19) 0.0028(17) -0.0352(19) O8 0.077(2) 0.077(2) 0.075(2) 0.0239(18) 0.0146(16) 0.0183(19) O4 0.087(2) 0.133(2) 0.073(2) 0.015(2) 0.0149(19) -0.022(2) C32 0.064(3) 0.058(2) 0.044(2) 0.0029(19) 0.0061(18) 0.001(2) C34 0.054(2) 0.051(2) 0.046(2) 0.0000(17) 0.0084(17) 0.0029(18) C28 0.061(2) 0.059(2) 0.050(2) 0.0025(19) 0.0069(18) -0.010(2) O11 0.082(2) 0.129(3) 0.071(2) 0.004(2) -0.0083(19) -0.042(2) C36 0.054(2) 0.049(2) 0.050(2) 0.0001(18) 0.0077(17) 0.0030(18) C12 0.062(2) 0.046(2) 0.052(2) 0.0016(17) 0.0029(18) -0.0040(18) O5 0.108(3) 0.070(2) 0.114(3) 0.006(2) 0.063(3) 0.001(2) C43 0.052(2) 0.0603(18) 0.057(2) 0.0036(15) 0.0036(19) -0.0093(17) C10 0.062(2) 0.046(2) 0.054(2) 0.0049(18) 0.0055(19) -0.0004(18) C11 0.070(3) 0.041(2) 0.058(2) -0.0004(18) 0.016(2) -0.0054(18) C33 0.049(2) 0.057(2) 0.0424(19) 0.0014(17) 0.0049(16) 0.0011(18) C29 0.051(2) 0.069(3) 0.053(2) -0.004(2) 0.0107(18) -0.005(2) C37 0.084(3) 0.045(2) 0.049(2) 0.0027(18) 0.010(2) 0.000(2) C35 0.052(2) 0.045(2) 0.050(2) -0.0024(17) 0.0049(17) -0.0038(17) O7 0.0548(19) 0.102(3) 0.126(3) 0.041(3) 0.018(2) 0.019(2) C4 0.053(2) 0.065(3) 0.045(2) 0.0007(19) 0.0052(17) -0.001(2) C8 0.052(2) 0.059(2) 0.0414(19) 0.0008(18) 0.0090(17) -0.0002(19) C5 0.051(2) 0.068(3) 0.057(2) 0.000(2) 0.0047(19) -0.001(2) C22 0.066(3) 0.044(2) 0.084(3) 0.003(2) 0.017(2) -0.009(2) C13 0.088(3) 0.046(2) 0.040(2) -0.0044(17) 0.0026(19) 0.000(2) C6 0.047(2) 0.088(4) 0.087(3) 0.003(3) -0.002(2) -0.001(2) C9 0.050(2) 0.053(2) 0.050(2) -0.0004(18) 0.0099(17) -0.0046(17) C30 0.058(3) 0.097(4) 0.079(3) -0.003(3) 0.017(2) -0.012(3) C46 0.056(2) 0.054(2) 0.069(3) 0.002(2) 0.006(2) -0.0010(19) C18 0.098(4) 0.059(3) 0.058(3) 0.000(2) 0.010(2) -0.010(3) C38 0.091(4) 0.061(3) 0.065(3) 0.002(2) 0.004(2) -0.017(3) C3 0.063(3) 0.085(3) 0.067(3) -0.015(3) 0.003(2) -0.006(3) O1 0.065(2) 0.098(3) 0.215(6) -0.068(4) 0.002(3) 0.013(2) C25 0.068(3) 0.104(4) 0.089(4) -0.008(3) 0.022(3) -0.028(3) C44 0.0747(14) 0.0698(12) 0.0782(13) 0.0020(9) 0.0046(10) 0.0044(10) C7 0.056(3) 0.065(3) 0.086(3) -0.006(2) 0.000(2) 0.008(2) C40 0.201(9) 0.051(3) 0.074(4) -0.004(3) -0.002(5) -0.005(4) C26 0.089(4) 0.079(4) 0.078(3) 0.000(3) 0.018(3) -0.028(3) C41 0.175(7) 0.048(3) 0.061(3) -0.001(2) 0.006(4) 0.024(4) C19 0.069(3) 0.050(2) 0.066(3) -0.002(2) 0.008(2) -0.003(2) C16 0.222(9) 0.046(3) 0.076(4) -0.004(3) 0.045(5) -0.020(5) C47 0.081(4) 0.097(4) 0.100(4) 0.008(3) 0.019(3) -0.028(3) C48 0.099(5) 0.069(4) 0.151(6) 0.009(4) -0.007(4) -0.022(3) C31 0.055(2) 0.064(3) 0.061(2) 0.001(2) 0.011(2) 0.004(2) C1 0.057(3) 0.090(4) 0.100(4) -0.006(3) -0.011(3) -0.014(3) C42 0.109(4) 0.058(3) 0.054(2) 0.005(2) 0.012(2) 0.015(3) C27 0.082(3) 0.059(3) 0.069(3) 0.004(2) 0.010(2) -0.018(2) C15 0.179(7) 0.050(3) 0.055(3) -0.007(2) 0.002(4) 0.027(4) C17 0.150(6) 0.059(3) 0.077(4) -0.001(3) 0.027(4) -0.030(4) C23 0.0952(16) 0.0928(15) 0.0980(16) -0.0020(10) 0.0088(11) 0.0045(10) C39 0.142(6) 0.074(4) 0.089(4) 0.003(3) -0.017(4) -0.031(4) C2 0.073(3) 0.088(4) 0.095(4) -0.013(3) -0.006(3) -0.019(3) C14 0.111(4) 0.055(3) 0.054(3) -0.007(2) 0.003(2) 0.013(3) C45 0.0926(16) 0.0847(15) 0.0900(15) -0.0077(10) 0.0080(11) 0.0085(10) C24 0.1053(18) 0.0943(15) 0.1040(17) 0.0028(10) 0.0090(11) 0.0063(11) O3 0.100(3) 0.079(2) 0.087(3) -0.002(2) -0.005(2) -0.028(2) C20 0.0981(16) 0.1045(15) 0.1036(18) 0.0006(11) 0.0102(11) -0.0171(10) C21 0.123(2) 0.1162(16) 0.127(2) 0.0011(11) 0.0091(11) -0.0017(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 Cl2 C14 1.712(7) . ? Cl4 C42 1.733(7) . ? Cl1 C15 1.731(7) . ? Cl3 C41 1.730(7) . ? O10 C43 1.331(6) . ? O10 C44 1.455(6) . ? O2 C8 1.217(5) . ? N1 C11 1.440(5) . ? N1 C12 1.467(6) . ? N1 H4 0.90(3) . ? O6 C22 1.308(6) . ? O6 C23 1.467(7) . ? O9 C43 1.187(5) . ? N2 C35 1.450(5) . ? N2 C36 1.462(5) . ? N2 H28 0.85(3) . ? O12 C46 1.291(6) . ? O12 C47 1.475(6) . ? O8 C32 1.217(5) . ? O4 C19 1.317(6) . ? O4 C20 1.445(8) . ? C32 C28 1.494(6) . ? C32 C33 1.496(6) . ? C34 C31 1.507(6) . ? C34 C35 1.535(6) . ? C34 C33 1.537(6) . ? C34 H34 0.9800 . ? C28 C29 1.398(6) . ? C28 C27 1.401(6) . ? O11 C46 1.198(6) . ? C36 C37 1.501(6) . ? C36 C33 1.590(5) . ? C36 H36 0.9800 . ? C12 C13 1.525(6) . ? C12 C9 1.542(4) . ? C12 H12 0.9800 . ? O5 C22 1.186(6) . ? C43 C35 1.529(6) . ? C10 C9 1.533(6) . ? C10 C7 1.537(7) . ? C10 C11 1.546(6) . ? C10 H10 0.9800 . ? C11 C22 1.524(6) . ? C11 C19 1.543(6) . ? C33 H33 0.9800 . ? C29 C30 1.397(7) . ? C29 C31 1.476(7) . ? C37 C38 1.388(7) . ? C37 C42 1.404(7) . ? C35 C46 1.553(6) . ? O7 C31 1.217(6) . ? C4 C3 1.389(7) . ? C4 C5 1.395(6) . ? C4 C8 1.477(6) . ? C8 C9 1.509(6) . ? C5 C6 1.416(7) . ? C5 C7 1.460(7) . ? C13 C18 1.371(7) . ? C13 C14 1.399(7) . ? C6 C1 1.373(8) . ? C6 H6 0.9300 . ? C9 H9 0.9800 . ? C30 C25 1.373(8) . ? C30 H30 0.9300 . ? C18 C17 1.379(7) . ? C18 H18 0.9300 . ? C38 C39 1.375(8) . ? C38 H38 0.9300 . ? C3 C2 1.366(7) . ? C3 H3 0.9300 . ? O1 C7 1.210(6) . ? C25 C26 1.379(9) . ? C25 H25 0.9300 . ? C44 C45 1.517(4) . ? C44 H44A 0.9700 . ? C44 H44B 0.9700 . ? C40 C41 1.357(11) . ? C40 C39 1.382(11) . ? C40 H40 0.9300 . ? C26 C27 1.380(8) . ? C26 H26 0.9300 . ? C41 C42 1.386(8) . ? C19 O3 1.194(6) . ? C16 C17 1.354(11) . ? C16 C15 1.375(11) . ? C16 H16 0.9300 . ? C47 C48 1.510(6) . ? C47 H47A 0.9700 . ? C47 H47B 0.9700 . ? C48 H48A 0.9600 . ? C48 H48B 0.9600 . ? C48 H48C 0.9600 . ? C1 C2 1.355(9) . ? C1 H1 0.9300 . ? C27 H27 0.9300 . ? C15 C14 1.415(9) . ? C17 H17 0.9300 . ? C23 C24 1.511(5) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C39 H39 0.9300 . ? C2 H2 0.9300 . ? C45 H45A 0.9600 . ? C45 H45B 0.9600 . ? C45 H45C 0.9600 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C20 C21 1.505(6) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C43 O10 C44 116.3(4) . . ? C11 N1 C12 107.0(3) . . ? C11 N1 H4 108(4) . . ? C12 N1 H4 109(3) . . ? C22 O6 C23 111.5(4) . . ? C35 N2 C36 107.9(3) . . ? C35 N2 H28 115(3) . . ? C36 N2 H28 111(3) . . ? C46 O12 C47 115.5(4) . . ? C19 O4 C20 116.1(5) . . ? O8 C32 C28 120.5(4) . . ? O8 C32 C33 120.1(4) . . ? C28 C32 C33 119.3(4) . . ? C31 C34 C35 112.2(3) . . ? C31 C34 C33 114.6(4) . . ? C35 C34 C33 102.0(3) . . ? C31 C34 H34 109.2 . . ? C35 C34 H34 109.2 . . ? C33 C34 H34 109.2 . . ? C29 C28 C27 120.2(4) . . ? C29 C28 C32 120.7(4) . . ? C27 C28 C32 119.1(4) . . ? N2 C36 C37 111.5(3) . . ? N2 C36 C33 102.1(3) . . ? C37 C36 C33 115.2(3) . . ? N2 C36 H36 109.2 . . ? C37 C36 H36 109.2 . . ? C33 C36 H36 109.2 . . ? N1 C12 C13 109.5(3) . . ? N1 C12 C9 103.3(3) . . ? C13 C12 C9 118.0(3) . . ? N1 C12 H12 108.6 . . ? C13 C12 H12 108.6 . . ? C9 C12 H12 108.6 . . ? O9 C43 O10 126.8(4) . . ? O9 C43 C35 125.8(4) . . ? O10 C43 C35 107.1(3) . . ? C9 C10 C7 113.8(4) . . ? C9 C10 C11 101.1(3) . . ? C7 C10 C11 109.6(4) . . ? C9 C10 H10 110.7 . . ? C7 C10 H10 110.7 . . ? C11 C10 H10 110.7 . . ? N1 C11 C22 110.5(3) . . ? N1 C11 C19 112.0(4) . . ? C22 C11 C19 105.1(3) . . ? N1 C11 C10 99.7(3) . . ? C22 C11 C10 117.2(4) . . ? C19 C11 C10 112.5(3) . . ? C32 C33 C34 116.6(3) . . ? C32 C33 C36 115.1(3) . . ? C34 C33 C36 104.3(3) . . ? C32 C33 H33 106.7 . . ? C34 C33 H33 106.7 . . ? C36 C33 H33 106.7 . . ? C30 C29 C28 119.4(4) . . ? C30 C29 C31 118.8(5) . . ? C28 C29 C31 121.8(4) . . ? C38 C37 C42 118.4(5) . . ? C38 C37 C36 120.1(4) . . ? C42 C37 C36 121.5(5) . . ? N2 C35 C43 111.3(3) . . ? N2 C35 C34 99.4(3) . . ? C43 C35 C34 116.6(3) . . ? N2 C35 C46 114.5(3) . . ? C43 C35 C46 105.6(3) . . ? C34 C35 C46 109.6(3) . . ? C3 C4 C5 120.0(4) . . ? C3 C4 C8 119.7(4) . . ? C5 C4 C8 120.3(4) . . ? O2 C8 C4 121.1(4) . . ? O2 C8 C9 119.7(4) . . ? C4 C8 C9 119.2(4) . . ? C4 C5 C6 118.2(5) . . ? C4 C5 C7 122.8(4) . . ? C6 C5 C7 118.9(4) . . ? O5 C22 O6 125.9(5) . . ? O5 C22 C11 124.5(4) . . ? O6 C22 C11 109.2(4) . . ? C18 C13 C14 118.6(5) . . ? C18 C13 C12 120.5(4) . . ? C14 C13 C12 120.9(5) . . ? C1 C6 C5 119.3(5) . . ? C1 C6 H6 120.3 . . ? C5 C6 H6 120.3 . . ? C8 C9 C10 115.5(3) . . ? C8 C9 C12 115.1(3) . . ? C10 C9 C12 105.3(3) . . ? C8 C9 H9 106.8 . . ? C10 C9 H9 106.8 . . ? C12 C9 H9 106.8 . . ? C25 C30 C29 119.4(6) . . ? C25 C30 H30 120.3 . . ? C29 C30 H30 120.3 . . ? O11 C46 O12 124.4(4) . . ? O11 C46 C35 124.7(4) . . ? O12 C46 C35 110.9(4) . . ? C13 C18 C17 122.5(6) . . ? C13 C18 H18 118.8 . . ? C17 C18 H18 118.8 . . ? C39 C38 C37 120.6(6) . . ? C39 C38 H38 119.7 . . ? C37 C38 H38 119.7 . . ? C2 C3 C4 120.9(5) . . ? C2 C3 H3 119.6 . . ? C4 C3 H3 119.6 . . ? C30 C25 C26 121.6(5) . . ? C30 C25 H25 119.2 . . ? C26 C25 H25 119.2 . . ? O10 C44 C45 107.5(4) . . ? O10 C44 H44A 110.2 . . ? C45 C44 H44A 110.2 . . ? O10 C44 H44B 110.2 . . ? C45 C44 H44B 110.2 . . ? H44A C44 H44B 108.5 . . ? O1 C7 C5 120.9(5) . . ? O1 C7 C10 120.3(5) . . ? C5 C7 C10 118.7(4) . . ? C41 C40 C39 119.9(6) . . ? C41 C40 H40 120.1 . . ? C39 C40 H40 120.1 . . ? C25 C26 C27 120.0(5) . . ? C25 C26 H26 120.0 . . ? C27 C26 H26 120.0 . . ? C40 C41 C42 120.8(6) . . ? C40 C41 Cl3 118.7(5) . . ? C42 C41 Cl3 120.5(7) . . ? O3 C19 O4 124.4(5) . . ? O3 C19 C11 121.7(4) . . ? O4 C19 C11 113.9(4) . . ? C17 C16 C15 120.6(6) . . ? C17 C16 H16 119.7 . . ? C15 C16 H16 119.7 . . ? O12 C47 C48 112.6(5) . . ? O12 C47 H47A 109.1 . . ? C48 C47 H47A 109.1 . . ? O12 C47 H47B 109.1 . . ? C48 C47 H47B 109.1 . . ? H47A C47 H47B 107.8 . . ? C47 C48 H48A 109.5 . . ? C47 C48 H48B 109.5 . . ? H48A C48 H48B 109.5 . . ? C47 C48 H48C 109.5 . . ? H48A C48 H48C 109.5 . . ? H48B C48 H48C 109.5 . . ? O7 C31 C29 120.7(4) . . ? O7 C31 C34 121.5(4) . . ? C29 C31 C34 117.6(4) . . ? C2 C1 C6 122.0(5) . . ? C2 C1 H1 119.0 . . ? C6 C1 H1 119.0 . . ? C41 C42 C37 119.9(6) . . ? C41 C42 Cl4 119.6(5) . . ? C37 C42 Cl4 120.5(4) . . ? C26 C27 C28 119.4(5) . . ? C26 C27 H27 120.3 . . ? C28 C27 H27 120.3 . . ? C16 C15 C14 120.5(6) . . ? C16 C15 Cl1 120.0(6) . . ? C14 C15 Cl1 119.4(7) . . ? C16 C17 C18 119.4(7) . . ? C16 C17 H17 120.3 . . ? C18 C17 H17 120.3 . . ? O6 C23 C24 105.8(5) . . ? O6 C23 H23A 110.6 . . ? C24 C23 H23A 110.6 . . ? O6 C23 H23B 110.6 . . ? C24 C23 H23B 110.6 . . ? H23A C23 H23B 108.7 . . ? C38 C39 C40 120.4(7) . . ? C38 C39 H39 119.8 . . ? C40 C39 H39 119.8 . . ? C1 C2 C3 119.6(5) . . ? C1 C2 H2 120.2 . . ? C3 C2 H2 120.2 . . ? C13 C14 C15 118.4(6) . . ? C13 C14 Cl2 121.4(4) . . ? C15 C14 Cl2 120.2(5) . . ? C44 C45 H45A 109.5 . . ? C44 C45 H45B 109.5 . . ? H45A C45 H45B 109.5 . . ? C44 C45 H45C 109.5 . . ? H45A C45 H45C 109.5 . . ? H45B C45 H45C 109.5 . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? O4 C20 C21 107.2(6) . . ? O4 C20 H20A 110.3 . . ? C21 C20 H20A 110.3 . . ? O4 C20 H20B 110.3 . . ? C21 C20 H20B 110.3 . . ? H20A C20 H20B 108.5 . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? 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 O8 C32 C28 C29 -177.3(4) . . . . ? C33 C32 C28 C29 2.9(6) . . . . ? O8 C32 C28 C27 1.5(7) . . . . ? C33 C32 C28 C27 -178.4(4) . . . . ? C35 N2 C36 C37 155.4(3) . . . . ? C35 N2 C36 C33 31.8(4) . . . . ? C11 N1 C12 C13 158.3(3) . . . . ? C11 N1 C12 C9 31.7(4) . . . . ? C44 O10 C43 O9 0.6(7) . . . . ? C44 O10 C43 C35 175.4(4) . . . . ? C12 N1 C11 C22 -172.2(4) . . . . ? C12 N1 C11 C19 70.9(4) . . . . ? C12 N1 C11 C10 -48.2(4) . . . . ? C9 C10 C11 N1 44.3(4) . . . . ? C7 C10 C11 N1 -76.1(4) . . . . ? C9 C10 C11 C22 163.4(3) . . . . ? C7 C10 C11 C22 43.0(5) . . . . ? C9 C10 C11 C19 -74.5(4) . . . . ? C7 C10 C11 C19 165.0(4) . . . . ? O8 C32 C33 C34 -164.6(4) . . . . ? C28 C32 C33 C34 15.2(5) . . . . ? O8 C32 C33 C36 72.8(5) . . . . ? C28 C32 C33 C36 -107.4(4) . . . . ? C31 C34 C33 C32 -33.1(5) . . . . ? C35 C34 C33 C32 -154.6(3) . . . . ? C31 C34 C33 C36 95.0(4) . . . . ? C35 C34 C33 C36 -26.5(4) . . . . ? N2 C36 C33 C32 127.5(4) . . . . ? C37 C36 C33 C32 6.4(5) . . . . ? N2 C36 C33 C34 -1.6(4) . . . . ? C37 C36 C33 C34 -122.6(4) . . . . ? C27 C28 C29 C30 -0.7(7) . . . . ? C32 C28 C29 C30 178.0(4) . . . . ? C27 C28 C29 C31 179.1(4) . . . . ? C32 C28 C29 C31 -2.1(6) . . . . ? N2 C36 C37 C38 -38.3(5) . . . . ? C33 C36 C37 C38 77.5(5) . . . . ? N2 C36 C37 C42 141.0(4) . . . . ? C33 C36 C37 C42 -103.2(5) . . . . ? C36 N2 C35 C43 -172.7(3) . . . . ? C36 N2 C35 C34 -49.2(4) . . . . ? C36 N2 C35 C46 67.5(4) . . . . ? O9 C43 C35 N2 -7.8(6) . . . . ? O10 C43 C35 N2 177.3(3) . . . . ? O9 C43 C35 C34 -120.9(5) . . . . ? O10 C43 C35 C34 64.2(5) . . . . ? O9 C43 C35 C46 117.1(5) . . . . ? O10 C43 C35 C46 -57.8(4) . . . . ? C31 C34 C35 N2 -78.1(4) . . . . ? C33 C34 C35 N2 45.1(4) . . . . ? C31 C34 C35 C43 41.6(5) . . . . ? C33 C34 C35 C43 164.8(3) . . . . ? C31 C34 C35 C46 161.5(4) . . . . ? C33 C34 C35 C46 -75.3(4) . . . . ? C3 C4 C8 O2 -6.4(6) . . . . ? C5 C4 C8 O2 175.2(4) . . . . ? C3 C4 C8 C9 171.9(4) . . . . ? C5 C4 C8 C9 -6.5(6) . . . . ? C3 C4 C5 C6 -2.0(7) . . . . ? C8 C4 C5 C6 176.4(4) . . . . ? C3 C4 C5 C7 176.3(5) . . . . ? C8 C4 C5 C7 -5.2(7) . . . . ? C23 O6 C22 O5 2.4(8) . . . . ? C23 O6 C22 C11 175.0(4) . . . . ? N1 C11 C22 O5 -4.7(7) . . . . ? C19 C11 C22 O5 116.3(5) . . . . ? C10 C11 C22 O5 -117.9(6) . . . . ? N1 C11 C22 O6 -177.5(4) . . . . ? C19 C11 C22 O6 -56.4(5) . . . . ? C10 C11 C22 O6 69.3(5) . . . . ? N1 C12 C13 C18 -33.9(5) . . . . ? C9 C12 C13 C18 83.8(5) . . . . ? N1 C12 C13 C14 144.3(4) . . . . ? C9 C12 C13 C14 -98.0(5) . . . . ? C4 C5 C6 C1 1.1(7) . . . . ? C7 C5 C6 C1 -177.3(5) . . . . ? O2 C8 C9 C10 -153.8(4) . . . . ? C4 C8 C9 C10 27.9(5) . . . . ? O2 C8 C9 C12 83.1(5) . . . . ? C4 C8 C9 C12 -95.2(4) . . . . ? C7 C10 C9 C8 -36.5(5) . . . . ? C11 C10 C9 C8 -153.9(3) . . . . ? C7 C10 C9 C12 91.6(4) . . . . ? C11 C10 C9 C12 -25.8(4) . . . . ? N1 C12 C9 C8 126.7(4) . . . . ? C13 C12 C9 C8 5.7(6) . . . . ? N1 C12 C9 C10 -1.7(4) . . . . ? C13 C12 C9 C10 -122.7(4) . . . . ? C28 C29 C30 C25 0.4(7) . . . . ? C31 C29 C30 C25 -179.4(5) . . . . ? C47 O12 C46 O11 -12.8(8) . . . . ? C47 O12 C46 C35 168.9(4) . . . . ? N2 C35 C46 O11 -111.8(5) . . . . ? C43 C35 C46 O11 125.3(5) . . . . ? C34 C35 C46 O11 -1.2(6) . . . . ? N2 C35 C46 O12 66.4(5) . . . . ? C43 C35 C46 O12 -56.4(5) . . . . ? C34 C35 C46 O12 177.1(4) . . . . ? C14 C13 C18 C17 -1.8(7) . . . . ? C12 C13 C18 C17 176.4(4) . . . . ? C42 C37 C38 C39 1.1(7) . . . . ? C36 C37 C38 C39 -179.6(5) . . . . ? C5 C4 C3 C2 0.7(8) . . . . ? C8 C4 C3 C2 -177.8(5) . . . . ? C29 C30 C25 C26 1.5(8) . . . . ? C43 O10 C44 C45 164.5(4) . . . . ? C4 C5 C7 O1 177.9(6) . . . . ? C6 C5 C7 O1 -3.7(8) . . . . ? C4 C5 C7 C10 -5.4(7) . . . . ? C6 C5 C7 C10 173.0(4) . . . . ? C9 C10 C7 O1 -157.1(6) . . . . ? C11 C10 C7 O1 -44.7(7) . . . . ? C9 C10 C7 C5 26.1(6) . . . . ? C11 C10 C7 C5 138.5(4) . . . . ? C30 C25 C26 C27 -3.1(9) . . . . ? C39 C40 C41 C42 -0.2(10) . . . . ? C39 C40 C41 Cl3 -179.2(5) . . . . ? C20 O4 C19 O3 2.8(8) . . . . ? C20 O4 C19 C11 -176.6(4) . . . . ? N1 C11 C19 O3 45.7(6) . . . . ? C22 C11 C19 O3 -74.3(6) . . . . ? C10 C11 C19 O3 157.0(5) . . . . ? N1 C11 C19 O4 -134.9(4) . . . . ? C22 C11 C19 O4 105.0(5) . . . . ? C10 C11 C19 O4 -23.6(6) . . . . ? C46 O12 C47 C48 -70.7(7) . . . . ? C30 C29 C31 O7 -14.2(7) . . . . ? C28 C29 C31 O7 165.9(5) . . . . ? C30 C29 C31 C34 162.6(4) . . . . ? C28 C29 C31 C34 -17.2(6) . . . . ? C35 C34 C31 O7 -33.1(6) . . . . ? C33 C34 C31 O7 -148.9(5) . . . . ? C35 C34 C31 C29 150.0(4) . . . . ? C33 C34 C31 C29 34.3(5) . . . . ? C5 C6 C1 C2 1.2(9) . . . . ? C40 C41 C42 C37 0.1(8) . . . . ? Cl3 C41 C42 C37 179.1(4) . . . . ? C40 C41 C42 Cl4 179.1(5) . . . . ? Cl3 C41 C42 Cl4 -1.9(6) . . . . ? C38 C37 C42 C41 -0.5(7) . . . . ? C36 C37 C42 C41 -179.8(4) . . . . ? C38 C37 C42 Cl4 -179.5(4) . . . . ? C36 C37 C42 Cl4 1.2(6) . . . . ? C25 C26 C27 C28 2.7(8) . . . . ? C29 C28 C27 C26 -0.8(7) . . . . ? C32 C28 C27 C26 -179.6(4) . . . . ? C17 C16 C15 C14 0.8(9) . . . . ? C17 C16 C15 Cl1 -176.9(5) . . . . ? C15 C16 C17 C18 0.3(9) . . . . ? C13 C18 C17 C16 0.3(8) . . . . ? C22 O6 C23 C24 -169.1(5) . . . . ? C37 C38 C39 C40 -1.2(9) . . . . ? C41 C40 C39 C38 0.8(10) . . . . ? C6 C1 C2 C3 -2.6(10) . . . . ? C4 C3 C2 C1 1.7(9) . . . . ? C18 C13 C14 C15 2.8(6) . . . . ? C12 C13 C14 C15 -175.4(4) . . . . ? C18 C13 C14 Cl2 -177.2(4) . . . . ? C12 C13 C14 Cl2 4.5(6) . . . . ? C16 C15 C14 C13 -2.4(8) . . . . ? Cl1 C15 C14 C13 175.3(3) . . . . ? C16 C15 C14 Cl2 177.7(5) . . . . ? Cl1 C15 C14 Cl2 -4.6(6) . . . . ? C19 O4 C20 C21 99.8(7) . . . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 62.78 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.471 _refine_diff_density_min -0.490 _refine_diff_density_rms 0.048 # Attachment '090305-cu2.cif.txt' data_090305-cu2 _database_code_depnum_ccdc_archive 'CCDC 742913' #TrackingRef '090305-cu2.cif.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C52 H42 Cl2 N4 O16' _chemical_formula_weight 1049.80 _chemical_absolute_configuration ad loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.965(5) _cell_length_b 30.381(5) _cell_length_c 10.583(5) _cell_angle_alpha 90.000(5) _cell_angle_beta 101.631(5) _cell_angle_gamma 90.000(5) _cell_volume 2508(2) _cell_formula_units_Z 2 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 4971 _cell_measurement_theta_min 2.9059 _cell_measurement_theta_max 62.6760 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.390 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1088 _exptl_absorpt_coefficient_mu 1.813 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6307 _exptl_absorpt_correction_T_max 0.7361 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET) (compiled Feb 27 2009,15:38:38) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Enhance Ultra (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'Gemini S Ultra, Oxford Diffraction' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 15.9149 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14302 _diffrn_reflns_av_R_equivalents 0.0289 _diffrn_reflns_av_sigmaI/netI 0.0551 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -35 _diffrn_reflns_limit_k_max 32 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.91 _diffrn_reflns_theta_max 62.83 _reflns_number_total 7313 _reflns_number_gt 5182 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlisPro (Oxford Diffraction Ltd.)' _computing_cell_refinement 'CrysAlisPro (Oxford Diffraction Ltd.)' _computing_data_reduction 'CrysAlisPro (Oxford Diffraction Ltd.)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 (L. J. Farrugia, 2001)' _computing_publication_material SHELXL-97 _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^)+(0.0355P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00071(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.033(17) _refine_ls_number_reflns 7313 _refine_ls_number_parameters 676 _refine_ls_number_restraints 24 _refine_ls_R_factor_all 0.0651 _refine_ls_R_factor_gt 0.0425 _refine_ls_wR_factor_ref 0.0934 _refine_ls_wR_factor_gt 0.0868 _refine_ls_goodness_of_fit_ref 1.005 _refine_ls_restrained_S_all 1.052 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.6696(2) -0.08344(6) 0.81241(16) 0.1164(6) Uani 1 1 d . . . Cl2 Cl 0.81558(18) 0.38244(5) 1.24252(14) 0.0995(5) Uani 1 1 d . . . O5 O 0.9069(3) 0.15724(9) 0.3624(3) 0.0597(7) Uani 1 1 d . . . N3 N 0.8809(4) 0.23571(10) 0.7793(3) 0.0487(8) Uani 1 1 d D . . O13 O 0.5624(3) 0.12748(9) 0.8717(3) 0.0547(7) Uani 1 1 d . . . C4 C 0.5897(5) -0.00104(11) 0.4523(4) 0.0454(9) Uani 1 1 d . . . C52 C 0.9099(4) 0.14436(12) 0.6898(4) 0.0476(9) Uani 1 1 d . . . H52 H 0.8628 0.1637 0.6241 0.057 Uiso 1 1 calc R . . C30 C 0.7547(4) 0.29802(11) 0.8854(4) 0.0422(9) Uani 1 1 d . . . N1 N 0.4701(4) 0.07051(11) 0.3662(4) 0.0567(9) Uani 1 1 d D . . C38 C 0.5874(4) 0.23923(12) 0.7448(4) 0.0414(9) Uani 1 1 d . . . O12 O 0.3810(3) 0.28525(9) 0.6138(3) 0.0624(7) Uani 1 1 d . . . O2 O 0.4391(4) -0.03449(11) 0.2220(3) 0.0849(9) Uani 1 1 d U . . O9 O 0.7197(4) 0.33859(9) 0.6618(3) 0.0755(9) Uani 1 1 d U . . O1 O 0.3661(4) 0.02997(12) 0.1259(3) 0.0857(10) Uani 1 1 d . . . C42 C 0.5143(5) 0.16679(12) 0.8047(4) 0.0454(9) Uani 1 1 d . . . C16 C 0.8838(5) 0.11406(13) 0.3160(4) 0.0518(10) Uani 1 1 d . . . O16 O 1.1289(4) 0.02853(12) 0.6120(4) 0.0929(11) Uani 1 1 d . . . C11 C 0.7392(4) 0.09155(13) 0.3339(4) 0.0456(9) Uani 1 1 d . . . N4 N 1.1274(4) 0.03498(13) 0.7256(5) 0.0709(11) Uani 1 1 d . . . C23 C 0.3745(5) 0.18633(15) 0.1305(5) 0.0668(12) Uani 1 1 d . . . H23 H 0.3299 0.1863 0.0423 0.080 Uiso 1 1 calc R . . C51 C 0.9791(4) 0.10440(13) 0.6600(4) 0.0542(10) Uani 1 1 d . . . H51 H 0.9740 0.0962 0.5746 0.065 Uiso 1 1 calc R . . O10 O 0.7635(5) 0.28172(11) 0.5436(3) 0.0874(10) Uani 1 1 d . . . C17 C 0.9155(6) 0.19031(16) 0.2766(5) 0.0695(13) Uani 1 1 d . . . C21 C 0.5080(4) 0.14907(12) 0.3227(4) 0.0470(9) Uani 1 1 d . . . C43 C 0.2507(6) 0.31142(15) 0.6322(6) 0.0744(12) Uani 1 1 d U . . C36 C 0.8271(4) 0.19758(11) 0.8491(4) 0.0455(9) Uani 1 1 d . . . H36 H 0.8548 0.2029 0.9424 0.055 Uiso 1 1 calc R . . C47 C 0.9115(4) 0.15516(11) 0.8171(4) 0.0415(9) Uani 1 1 d . . . C7 C 0.5546(4) 0.02967(12) 0.3356(4) 0.0461(9) Uani 1 1 d . . . C29 C 0.6171(5) 0.30593(13) 0.9444(5) 0.0627(12) Uani 1 1 d . . . H29 H 0.5108 0.2938 0.9089 0.075 Uiso 1 1 calc R . . C48 C 0.9919(5) 0.12704(13) 0.9134(4) 0.0551(10) Uani 1 1 d . . . H48 H 0.9977 0.1347 0.9993 0.066 Uiso 1 1 calc R . . C1 C 0.6414(6) -0.05176(14) 0.6727(5) 0.0665(12) Uani 1 1 d . . . N2 N 0.2986(5) 0.26421(17) 0.1321(7) 0.0937(16) Uani 1 1 d . . . C41 C 0.3445(5) 0.17524(13) 0.7503(4) 0.0581(11) Uani 1 1 d . . . H41 H 0.2616 0.1541 0.7553 0.070 Uiso 1 1 calc R . . C28 C 0.6339(6) 0.33131(15) 1.0544(5) 0.0679(12) Uani 1 1 d . . . H28 H 0.5409 0.3361 1.0935 0.081 Uiso 1 1 calc R . . C31 C 0.9099(5) 0.31694(12) 0.9402(4) 0.0508(10) Uani 1 1 d . . . H31 H 1.0037 0.3125 0.9018 0.061 Uiso 1 1 calc R . . C27 C 0.7905(5) 0.34934(13) 1.1045(4) 0.0570(11) Uani 1 1 d . . . C24 C 0.3721(5) 0.22362(13) 0.2004(5) 0.0631(12) Uani 1 1 d . . . C22 C 0.4435(5) 0.14859(14) 0.1911(4) 0.0639(12) Uani 1 1 d . . . H22 H 0.4468 0.1229 0.1440 0.077 Uiso 1 1 calc R . . C33 C 0.7429(4) 0.26898(11) 0.7643(4) 0.0432(9) Uani 1 1 d . . . C50 C 1.0539(4) 0.07769(12) 0.7581(4) 0.0503(10) Uani 1 1 d . . . C13 C 0.8370(5) 0.02737(13) 0.2405(4) 0.0537(10) Uani 1 1 d . . . C6 C 0.4748(5) -0.03971(13) 0.6152(4) 0.0596(11) Uani 1 1 d . . . H6 H 0.3820 -0.0486 0.6500 0.072 Uiso 1 1 calc R . . C5 C 0.4515(5) -0.01425(13) 0.5051(4) 0.0524(10) Uani 1 1 d . . . H5 H 0.3413 -0.0058 0.4655 0.063 Uiso 1 1 calc R . . C14 C 0.9822(5) 0.04941(15) 0.2246(4) 0.0637(12) Uani 1 1 d . . . H14 H 1.0638 0.0352 0.1875 0.076 Uiso 1 1 calc R . . C3 C 0.7521(5) -0.01380(13) 0.5123(4) 0.0550(10) Uani 1 1 d . . . H3 H 0.8459 -0.0050 0.4785 0.066 Uiso 1 1 calc R . . O7 O 0.2903(6) 0.29693(13) 0.1963(6) 0.1324(19) Uani 1 1 d . . . C2 C 0.7770(6) -0.03959(14) 0.6222(4) 0.0632(12) Uani 1 1 d . . . H2 H 0.8869 -0.0485 0.6612 0.076 Uiso 1 1 calc R . . C32 C 0.9297(5) 0.34240(13) 1.0507(4) 0.0549(11) Uani 1 1 d . . . H32 H 1.0356 0.3545 1.0874 0.066 Uiso 1 1 calc R . . C15 C 1.0064(5) 0.09277(15) 0.2640(4) 0.0600(11) Uani 1 1 d . . . H15 H 1.1057 0.1075 0.2553 0.072 Uiso 1 1 calc R . . C40 C 0.2967(5) 0.21450(14) 0.6888(4) 0.0586(11) Uani 1 1 d . . . H40 H 0.1829 0.2194 0.6494 0.070 Uiso 1 1 calc R . . C49 C 1.0631(5) 0.08811(13) 0.8850(4) 0.0605(11) Uani 1 1 d . . . H49 H 1.1162 0.0693 0.9502 0.073 Uiso 1 1 calc R . . C10 C 0.5888(4) 0.10795(12) 0.3882(4) 0.0488(10) Uani 1 1 d . . . H10 H 0.6253 0.1133 0.4810 0.059 Uiso 1 1 calc R . . C26 C 0.5011(6) 0.18725(14) 0.3903(5) 0.0679(12) Uani 1 1 d . . . H26 H 0.5421 0.1875 0.4790 0.081 Uiso 1 1 calc R . . C39 C 0.4190(5) 0.24663(12) 0.6861(4) 0.0500(10) Uani 1 1 d . . . C37 C 0.6353(4) 0.19838(12) 0.8011(4) 0.0425(9) Uani 1 1 d . . . C12 C 0.7177(4) 0.04791(12) 0.2977(4) 0.0464(9) Uani 1 1 d . . . O6 O 0.9063(7) 0.18303(11) 0.1670(4) 0.139(2) Uani 1 1 d . . . C25 C 0.4341(6) 0.22540(14) 0.3289(5) 0.0735(14) Uani 1 1 d . . . H25 H 0.4319 0.2515 0.3746 0.088 Uiso 1 1 calc R . . C34 C 0.7476(5) 0.29636(14) 0.6441(4) 0.0518(10) Uani 1 1 d . . . C8 C 0.4420(5) 0.00877(16) 0.2149(5) 0.0599(11) Uani 1 1 d . . . C9 C 0.3472(7) -0.05723(17) 0.1063(5) 0.0923(14) Uani 1 1 d U . . H9A H 0.3538 -0.0885 0.1204 0.138 Uiso 1 1 calc R . . H9B H 0.3984 -0.0499 0.0343 0.138 Uiso 1 1 calc R . . H9C H 0.2293 -0.0482 0.0885 0.138 Uiso 1 1 calc R . . C35 C 0.7072(6) 0.36768(16) 0.5508(5) 0.0849(13) Uani 1 1 d U . . H35A H 0.6881 0.3973 0.5761 0.127 Uiso 1 1 calc R . . H35B H 0.6133 0.3585 0.4841 0.127 Uiso 1 1 calc R . . H35C H 0.8118 0.3664 0.5192 0.127 Uiso 1 1 calc R . . C18 C 0.9409(7) 0.23353(16) 0.3392(5) 0.0908(16) Uani 1 1 d . . . H18A H 0.9462 0.2302 0.4302 0.136 Uiso 1 1 calc R . . H18B H 0.8470 0.2525 0.3033 0.136 Uiso 1 1 calc R . . H18C H 1.0461 0.2462 0.3252 0.136 Uiso 1 1 calc R . . C44 C 0.2218(7) 0.34731(18) 0.5327(6) 0.1013(16) Uani 1 1 d U . . H44A H 0.3015 0.3440 0.4763 0.152 Uiso 1 1 calc R . . H44B H 0.2384 0.3754 0.5747 0.152 Uiso 1 1 calc R . . H44C H 0.1068 0.3454 0.4832 0.152 Uiso 1 1 calc R . . O3 O 0.8016(4) -0.01515(9) 0.1919(3) 0.0669(8) Uani 1 1 d . . . O14 O 0.5042(5) 0.08953(11) 0.6860(4) 0.0892(10) Uani 1 1 d . . . O4 O 1.0391(5) -0.04266(13) 0.3162(5) 0.1114(13) Uani 1 1 d . . . C45 C 0.5510(6) 0.08955(14) 0.7996(5) 0.0623(11) Uani 1 1 d . . . O8 O 0.2538(6) 0.26270(15) 0.0158(6) 0.1244(18) Uani 1 1 d . . . O15 O 1.1772(6) 0.00931(12) 0.8112(4) 0.1160(15) Uani 1 1 d . . . C19 C 0.9136(7) -0.04820(16) 0.2361(5) 0.0764(14) Uani 1 1 d . . . O11 O 0.1728(5) 0.30593(11) 0.7134(4) 0.0978(12) Uani 1 1 d . . . C46 C 0.6051(6) 0.05123(15) 0.8849(5) 0.0839(15) Uani 1 1 d . . . H46A H 0.6375 0.0611 0.9727 0.126 Uiso 1 1 calc R . . H46B H 0.7010 0.0371 0.8598 0.126 Uiso 1 1 calc R . . H46C H 0.5118 0.0308 0.8775 0.126 Uiso 1 1 calc R . . C20 C 0.8545(9) -0.08954(17) 0.1667(6) 0.116(2) Uani 1 1 d . . . H20A H 0.7487 -0.0842 0.1068 0.173 Uiso 1 1 calc R . . H20B H 0.8370 -0.1116 0.2276 0.173 Uiso 1 1 calc R . . H20C H 0.9395 -0.0995 0.1206 0.173 Uiso 1 1 calc R . . H27 H 0.985(3) 0.2462(11) 0.807(3) 0.050(11) Uiso 1 1 d D . . H1 H 0.405(6) 0.0654(18) 0.421(5) 0.12(2) Uiso 1 1 d 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 0.1137(10) 0.1354(13) 0.0988(12) 0.0698(10) 0.0177(9) 0.0173(9) Cl2 0.1135(10) 0.1144(11) 0.0736(9) -0.0477(8) 0.0261(8) -0.0088(8) O5 0.0697(17) 0.0649(19) 0.0461(17) 0.0022(15) 0.0158(14) -0.0073(14) N3 0.0380(18) 0.0404(18) 0.068(2) -0.0040(16) 0.0122(16) -0.0013(15) O13 0.0636(16) 0.0461(15) 0.0548(18) 0.0038(14) 0.0129(14) -0.0038(12) C4 0.045(2) 0.046(2) 0.046(2) -0.0061(18) 0.0099(19) 0.0040(17) C52 0.050(2) 0.049(2) 0.041(2) 0.0000(18) 0.0007(18) 0.0049(18) C30 0.048(2) 0.0366(19) 0.044(2) 0.0023(17) 0.0118(18) 0.0010(17) N1 0.0464(18) 0.049(2) 0.079(3) 0.0045(18) 0.0229(19) 0.0056(16) C38 0.041(2) 0.043(2) 0.041(2) -0.0060(18) 0.0098(17) 0.0005(17) O12 0.0552(15) 0.0669(18) 0.067(2) 0.0145(16) 0.0160(14) 0.0151(14) O2 0.103(2) 0.072(2) 0.079(2) -0.0101(17) 0.0168(18) -0.0107(18) O9 0.114(2) 0.0497(19) 0.065(2) 0.0007(13) 0.0232(19) -0.0064(16) O1 0.084(2) 0.109(3) 0.055(2) 0.009(2) -0.0075(18) 0.011(2) C42 0.048(2) 0.043(2) 0.046(3) -0.0027(18) 0.0126(19) -0.0012(18) C16 0.052(2) 0.057(3) 0.046(3) 0.006(2) 0.008(2) 0.002(2) O16 0.074(2) 0.094(3) 0.109(3) -0.042(2) 0.014(2) 0.0185(18) C11 0.042(2) 0.056(2) 0.037(2) 0.0047(19) 0.0061(17) 0.0050(18) N4 0.061(2) 0.062(3) 0.084(3) -0.014(2) 0.002(2) 0.0076(19) C23 0.071(3) 0.078(3) 0.048(3) 0.014(3) 0.005(2) 0.011(2) C51 0.054(2) 0.062(3) 0.044(3) -0.016(2) 0.0023(19) 0.005(2) O10 0.128(3) 0.088(2) 0.055(2) -0.0017(19) 0.041(2) 0.009(2) C17 0.097(3) 0.066(3) 0.053(3) 0.001(3) 0.031(3) 0.004(3) C21 0.048(2) 0.051(2) 0.045(2) -0.003(2) 0.0136(19) 0.0019(18) C43 0.061(3) 0.071(3) 0.095(4) -0.010(2) 0.024(3) 0.011(2) C36 0.048(2) 0.044(2) 0.044(2) -0.0055(19) 0.0102(18) 0.0022(17) C47 0.0391(19) 0.044(2) 0.041(2) -0.0045(18) 0.0066(17) -0.0024(16) C7 0.046(2) 0.048(2) 0.045(2) 0.0046(19) 0.0105(18) 0.0082(18) C29 0.061(2) 0.061(3) 0.072(3) -0.022(2) 0.029(2) -0.010(2) C48 0.074(3) 0.052(2) 0.039(2) -0.001(2) 0.010(2) 0.003(2) C1 0.079(3) 0.059(3) 0.061(3) 0.012(2) 0.015(3) 0.008(2) N2 0.064(3) 0.082(3) 0.137(5) 0.040(4) 0.024(3) 0.017(2) C41 0.047(2) 0.056(3) 0.074(3) -0.004(2) 0.019(2) -0.0122(19) C28 0.066(3) 0.075(3) 0.072(3) -0.018(3) 0.038(3) -0.005(2) C31 0.044(2) 0.053(2) 0.056(3) -0.007(2) 0.0126(19) -0.0039(18) C27 0.075(3) 0.053(2) 0.044(3) -0.013(2) 0.015(2) 0.001(2) C24 0.060(3) 0.046(3) 0.086(4) 0.017(3) 0.023(3) 0.010(2) C22 0.083(3) 0.059(3) 0.046(3) 0.000(2) 0.004(2) 0.013(2) C33 0.047(2) 0.039(2) 0.047(2) -0.0028(17) 0.0159(18) -0.0019(17) C50 0.041(2) 0.039(2) 0.069(3) -0.008(2) 0.007(2) 0.0044(17) C13 0.060(3) 0.051(2) 0.052(3) 0.007(2) 0.017(2) 0.016(2) C6 0.068(3) 0.053(2) 0.061(3) 0.009(2) 0.020(2) -0.001(2) C5 0.050(2) 0.052(2) 0.056(3) -0.001(2) 0.010(2) 0.0021(19) C14 0.053(3) 0.071(3) 0.071(3) 0.012(3) 0.024(2) 0.018(2) C3 0.053(2) 0.058(2) 0.054(3) 0.001(2) 0.010(2) 0.008(2) O7 0.129(3) 0.060(2) 0.204(6) 0.017(3) 0.024(3) 0.031(2) C2 0.063(3) 0.065(3) 0.059(3) 0.007(2) 0.008(2) 0.008(2) C32 0.053(2) 0.056(3) 0.053(3) -0.011(2) 0.005(2) -0.0020(19) C15 0.045(2) 0.078(3) 0.059(3) 0.013(2) 0.016(2) 0.007(2) C40 0.047(2) 0.060(3) 0.069(3) -0.003(2) 0.010(2) -0.001(2) C49 0.069(3) 0.048(2) 0.062(3) 0.013(2) 0.008(2) 0.015(2) C10 0.052(2) 0.056(2) 0.040(2) 0.0010(19) 0.0115(18) 0.0064(19) C26 0.077(3) 0.072(3) 0.049(3) -0.008(2) 0.000(2) 0.022(2) C39 0.056(2) 0.046(2) 0.052(3) 0.004(2) 0.021(2) 0.0039(19) C37 0.042(2) 0.042(2) 0.045(2) -0.0038(18) 0.0113(17) 0.0005(17) C12 0.044(2) 0.052(2) 0.044(2) 0.0071(19) 0.0101(18) 0.0075(18) O6 0.306(7) 0.066(2) 0.057(3) 0.009(2) 0.061(4) 0.026(3) C25 0.086(3) 0.051(3) 0.079(4) -0.011(3) 0.006(3) 0.019(2) C34 0.056(2) 0.058(3) 0.042(3) -0.001(2) 0.012(2) -0.002(2) C8 0.052(2) 0.074(3) 0.054(3) 0.001(2) 0.009(2) -0.002(2) C9 0.0948(16) 0.0920(16) 0.0875(16) -0.0098(10) 0.0125(10) -0.0051(10) C35 0.0908(16) 0.0826(15) 0.0807(15) 0.0172(10) 0.0157(10) -0.0029(10) C18 0.124(4) 0.066(3) 0.092(4) -0.006(3) 0.045(4) -0.009(3) C44 0.1018(19) 0.1002(18) 0.1015(19) 0.0055(10) 0.0198(11) 0.0042(10) O3 0.0737(18) 0.0598(18) 0.070(2) -0.0030(16) 0.0219(16) 0.0157(16) O14 0.141(3) 0.064(2) 0.061(2) -0.0123(19) 0.017(2) 0.004(2) O4 0.111(3) 0.089(3) 0.124(4) 0.001(3) 0.000(3) 0.044(2) C45 0.073(3) 0.046(3) 0.073(4) -0.005(3) 0.025(3) -0.006(2) O8 0.108(3) 0.139(4) 0.129(4) 0.076(3) 0.031(3) 0.053(3) O15 0.155(4) 0.062(2) 0.116(4) 0.002(2) -0.007(3) 0.046(2) C19 0.088(4) 0.068(3) 0.077(4) 0.003(3) 0.026(3) 0.025(3) O11 0.104(3) 0.077(2) 0.129(3) 0.013(2) 0.063(3) 0.031(2) C46 0.101(4) 0.054(3) 0.099(4) 0.013(3) 0.026(3) 0.000(3) C20 0.174(6) 0.062(3) 0.110(5) -0.007(4) 0.028(5) 0.025(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C1 1.740(5) . ? Cl2 C27 1.751(4) . ? O5 C17 1.365(5) . ? O5 C16 1.400(5) . ? N3 C33 1.478(4) . ? N3 C36 1.484(5) . ? N3 H27 0.88(2) . ? O13 C45 1.375(5) . ? O13 C42 1.402(4) . ? C4 C3 1.376(5) . ? C4 C5 1.391(5) . ? C4 C7 1.528(5) . ? C52 C47 1.385(5) . ? C52 C51 1.395(5) . ? C52 H52 0.9300 . ? C30 C31 1.380(5) . ? C30 C29 1.388(5) . ? C30 C33 1.544(5) . ? N1 C10 1.468(5) . ? N1 C7 1.478(5) . ? N1 H1 0.86(3) . ? C38 C39 1.378(5) . ? C38 C37 1.396(5) . ? C38 C33 1.513(5) . ? O12 C43 1.352(5) . ? O12 C39 1.400(5) . ? O2 C8 1.317(5) . ? O2 C9 1.466(6) . ? O9 C34 1.322(5) . ? O9 C35 1.457(5) . ? O1 C8 1.199(5) . ? C42 C37 1.366(5) . ? C42 C41 1.383(5) . ? C16 C15 1.375(5) . ? C16 C11 1.385(5) . ? O16 N4 1.221(5) . ? C11 C12 1.381(5) . ? C11 C10 1.513(5) . ? N4 O15 1.200(5) . ? N4 C50 1.492(5) . ? C23 C24 1.355(6) . ? C23 C22 1.373(6) . ? C23 H23 0.9300 . ? C51 C50 1.357(6) . ? C51 H51 0.9300 . ? O10 C34 1.183(5) . ? C17 O6 1.168(6) . ? C17 C18 1.467(6) . ? C21 C26 1.370(5) . ? C21 C22 1.383(6) . ? C21 C10 1.509(5) . ? C43 O11 1.169(6) . ? C43 C44 1.501(7) . ? C36 C37 1.510(5) . ? C36 C47 1.523(5) . ? C36 H36 0.9800 . ? C47 C48 1.384(5) . ? C7 C12 1.538(5) . ? C7 C8 1.542(6) . ? C29 C28 1.380(6) . ? C29 H29 0.9300 . ? C48 C49 1.371(5) . ? C48 H48 0.9300 . ? C1 C2 1.350(6) . ? C1 C6 1.392(6) . ? N2 O8 1.211(7) . ? N2 O7 1.214(7) . ? N2 C24 1.488(6) . ? C41 C40 1.375(6) . ? C41 H41 0.9300 . ? C28 C27 1.368(6) . ? C28 H28 0.9300 . ? C31 C32 1.384(5) . ? C31 H31 0.9300 . ? C27 C32 1.360(5) . ? C24 C25 1.351(7) . ? C22 H22 0.9300 . ? C33 C34 1.526(6) . ? C50 C49 1.367(6) . ? C13 C12 1.375(5) . ? C13 C14 1.376(6) . ? C13 O3 1.398(5) . ? C6 C5 1.379(6) . ? C6 H6 0.9300 . ? C5 H5 0.9300 . ? C14 C15 1.383(6) . ? C14 H14 0.9300 . ? C3 C2 1.383(6) . ? C3 H3 0.9300 . ? C2 H2 0.9300 . ? C32 H32 0.9300 . ? C15 H15 0.9300 . ? C40 C39 1.383(5) . ? C40 H40 0.9300 . ? C49 H49 0.9300 . ? C10 H10 0.9800 . ? C26 C25 1.382(6) . ? C26 H26 0.9300 . ? C25 H25 0.9300 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C35 H35A 0.9600 . ? C35 H35B 0.9600 . ? C35 H35C 0.9600 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C44 H44A 0.9600 . ? C44 H44B 0.9600 . ? C44 H44C 0.9600 . ? O3 C19 1.361(6) . ? O14 C45 1.186(6) . ? O4 C19 1.186(6) . ? C45 C46 1.483(6) . ? C19 C20 1.483(7) . ? C46 H46A 0.9600 . ? C46 H46B 0.9600 . ? C46 H46C 0.9600 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C17 O5 C16 118.5(3) . . ? C33 N3 C36 107.7(3) . . ? C33 N3 H27 115(2) . . ? C36 N3 H27 118(2) . . ? C45 O13 C42 116.9(3) . . ? C3 C4 C5 118.7(4) . . ? C3 C4 C7 123.1(3) . . ? C5 C4 C7 118.0(3) . . ? C47 C52 C51 120.0(4) . . ? C47 C52 H52 120.0 . . ? C51 C52 H52 120.0 . . ? C31 C30 C29 117.4(3) . . ? C31 C30 C33 119.1(3) . . ? C29 C30 C33 123.4(3) . . ? C10 N1 C7 112.2(3) . . ? C10 N1 H1 119(4) . . ? C7 N1 H1 111(4) . . ? C39 C38 C37 119.7(3) . . ? C39 C38 C33 131.2(3) . . ? C37 C38 C33 109.1(3) . . ? C43 O12 C39 120.1(3) . . ? C8 O2 C9 115.7(4) . . ? C34 O9 C35 117.5(4) . . ? C37 C42 C41 119.6(3) . . ? C37 C42 O13 119.3(3) . . ? C41 C42 O13 120.9(3) . . ? C15 C16 C11 120.0(4) . . ? C15 C16 O5 121.8(3) . . ? C11 C16 O5 117.9(3) . . ? C12 C11 C16 119.7(3) . . ? C12 C11 C10 111.0(3) . . ? C16 C11 C10 129.3(4) . . ? O15 N4 O16 124.8(4) . . ? O15 N4 C50 118.5(5) . . ? O16 N4 C50 116.7(4) . . ? C24 C23 C22 119.5(4) . . ? C24 C23 H23 120.3 . . ? C22 C23 H23 120.3 . . ? C50 C51 C52 118.7(4) . . ? C50 C51 H51 120.7 . . ? C52 C51 H51 120.7 . . ? O6 C17 O5 121.3(4) . . ? O6 C17 C18 126.4(5) . . ? O5 C17 C18 112.3(4) . . ? C26 C21 C22 119.2(4) . . ? C26 C21 C10 121.3(4) . . ? C22 C21 C10 119.4(3) . . ? O11 C43 O12 123.9(5) . . ? O11 C43 C44 126.2(5) . . ? O12 C43 C44 109.9(5) . . ? N3 C36 C37 101.2(3) . . ? N3 C36 C47 111.4(3) . . ? C37 C36 C47 113.6(3) . . ? N3 C36 H36 110.1 . . ? C37 C36 H36 110.1 . . ? C47 C36 H36 110.1 . . ? C48 C47 C52 118.9(3) . . ? C48 C47 C36 121.2(3) . . ? C52 C47 C36 120.0(3) . . ? N1 C7 C4 110.7(3) . . ? N1 C7 C12 101.6(3) . . ? C4 C7 C12 113.8(3) . . ? N1 C7 C8 108.2(3) . . ? C4 C7 C8 113.5(3) . . ? C12 C7 C8 108.2(3) . . ? C28 C29 C30 121.6(4) . . ? C28 C29 H29 119.2 . . ? C30 C29 H29 119.2 . . ? C49 C48 C47 121.4(4) . . ? C49 C48 H48 119.3 . . ? C47 C48 H48 119.3 . . ? C2 C1 C6 121.5(4) . . ? C2 C1 Cl1 120.8(4) . . ? C6 C1 Cl1 117.7(3) . . ? O8 N2 O7 124.2(5) . . ? O8 N2 C24 118.0(6) . . ? O7 N2 C24 117.8(6) . . ? C40 C41 C42 120.8(4) . . ? C40 C41 H41 119.6 . . ? C42 C41 H41 119.6 . . ? C27 C28 C29 118.5(4) . . ? C27 C28 H28 120.8 . . ? C29 C28 H28 120.8 . . ? C30 C31 C32 121.8(3) . . ? C30 C31 H31 119.1 . . ? C32 C31 H31 119.1 . . ? C32 C27 C28 122.1(4) . . ? C32 C27 Cl2 118.2(3) . . ? C28 C27 Cl2 119.7(3) . . ? C25 C24 C23 122.7(4) . . ? C25 C24 N2 118.9(5) . . ? C23 C24 N2 118.4(5) . . ? C23 C22 C21 119.6(4) . . ? C23 C22 H22 120.2 . . ? C21 C22 H22 120.2 . . ? N3 C33 C38 100.2(3) . . ? N3 C33 C34 108.6(3) . . ? C38 C33 C34 111.7(3) . . ? N3 C33 C30 112.5(3) . . ? C38 C33 C30 111.5(3) . . ? C34 C33 C30 111.9(3) . . ? C51 C50 C49 122.8(3) . . ? C51 C50 N4 118.4(4) . . ? C49 C50 N4 118.8(4) . . ? C12 C13 C14 120.4(4) . . ? C12 C13 O3 118.4(3) . . ? C14 C13 O3 121.1(4) . . ? C5 C6 C1 118.1(4) . . ? C5 C6 H6 121.0 . . ? C1 C6 H6 121.0 . . ? C6 C5 C4 121.2(4) . . ? C6 C5 H5 119.4 . . ? C4 C5 H5 119.4 . . ? C13 C14 C15 119.7(4) . . ? C13 C14 H14 120.1 . . ? C15 C14 H14 120.1 . . ? C4 C3 C2 120.6(4) . . ? C4 C3 H3 119.7 . . ? C2 C3 H3 119.7 . . ? C1 C2 C3 119.9(4) . . ? C1 C2 H2 120.1 . . ? C3 C2 H2 120.1 . . ? C27 C32 C31 118.5(4) . . ? C27 C32 H32 120.8 . . ? C31 C32 H32 120.8 . . ? C16 C15 C14 120.1(4) . . ? C16 C15 H15 119.9 . . ? C14 C15 H15 119.9 . . ? C41 C40 C39 119.5(4) . . ? C41 C40 H40 120.2 . . ? C39 C40 H40 120.2 . . ? C50 C49 C48 118.2(4) . . ? C50 C49 H49 120.9 . . ? C48 C49 H49 120.9 . . ? N1 C10 C21 111.6(3) . . ? N1 C10 C11 102.7(3) . . ? C21 C10 C11 113.3(3) . . ? N1 C10 H10 109.7 . . ? C21 C10 H10 109.7 . . ? C11 C10 H10 109.7 . . ? C21 C26 C25 121.1(4) . . ? C21 C26 H26 119.4 . . ? C25 C26 H26 119.4 . . ? C38 C39 C40 120.1(4) . . ? C38 C39 O12 117.8(3) . . ? C40 C39 O12 121.8(4) . . ? C42 C37 C38 120.2(3) . . ? C42 C37 C36 130.6(3) . . ? C38 C37 C36 109.2(3) . . ? C13 C12 C11 120.0(3) . . ? C13 C12 C7 130.3(3) . . ? C11 C12 C7 109.7(3) . . ? C24 C25 C26 117.9(4) . . ? C24 C25 H25 121.1 . . ? C26 C25 H25 121.1 . . ? O10 C34 O9 122.9(4) . . ? O10 C34 C33 124.7(4) . . ? O9 C34 C33 112.2(3) . . ? O1 C8 O2 124.7(4) . . ? O1 C8 C7 123.1(4) . . ? O2 C8 C7 112.2(4) . . ? O2 C9 H9A 109.5 . . ? O2 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? O2 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? O9 C35 H35A 109.5 . . ? O9 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? O9 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C43 C44 H44A 109.5 . . ? C43 C44 H44B 109.5 . . ? H44A C44 H44B 109.5 . . ? C43 C44 H44C 109.5 . . ? H44A C44 H44C 109.5 . . ? H44B C44 H44C 109.5 . . ? C19 O3 C13 119.1(4) . . ? O14 C45 O13 122.4(4) . . ? O14 C45 C46 127.7(5) . . ? O13 C45 C46 110.0(4) . . ? O4 C19 O3 122.7(5) . . ? O4 C19 C20 127.8(5) . . ? O3 C19 C20 109.5(5) . . ? C45 C46 H46A 109.5 . . ? C45 C46 H46B 109.5 . . ? H46A C46 H46B 109.5 . . ? C45 C46 H46C 109.5 . . ? H46A C46 H46C 109.5 . . ? H46B C46 H46C 109.5 . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 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 C45 O13 C42 C37 -114.3(4) . . . . ? C45 O13 C42 C41 70.4(5) . . . . ? C17 O5 C16 C15 65.8(5) . . . . ? C17 O5 C16 C11 -119.8(4) . . . . ? C15 C16 C11 C12 -0.9(6) . . . . ? O5 C16 C11 C12 -175.5(3) . . . . ? C15 C16 C11 C10 -179.7(4) . . . . ? O5 C16 C11 C10 5.8(6) . . . . ? C47 C52 C51 C50 -2.9(5) . . . . ? C16 O5 C17 O6 -1.0(7) . . . . ? C16 O5 C17 C18 -179.7(4) . . . . ? C39 O12 C43 O11 6.3(7) . . . . ? C39 O12 C43 C44 -172.9(4) . . . . ? C33 N3 C36 C37 32.7(4) . . . . ? C33 N3 C36 C47 153.8(3) . . . . ? C51 C52 C47 C48 4.0(5) . . . . ? C51 C52 C47 C36 -176.6(3) . . . . ? N3 C36 C47 C48 131.0(4) . . . . ? C37 C36 C47 C48 -115.4(4) . . . . ? N3 C36 C47 C52 -48.4(4) . . . . ? C37 C36 C47 C52 65.1(4) . . . . ? C10 N1 C7 C4 103.7(4) . . . . ? C10 N1 C7 C12 -17.5(4) . . . . ? C10 N1 C7 C8 -131.3(4) . . . . ? C3 C4 C7 N1 -118.2(4) . . . . ? C5 C4 C7 N1 57.5(4) . . . . ? C3 C4 C7 C12 -4.5(5) . . . . ? C5 C4 C7 C12 171.1(3) . . . . ? C3 C4 C7 C8 119.9(4) . . . . ? C5 C4 C7 C8 -64.4(4) . . . . ? C31 C30 C29 C28 -0.7(6) . . . . ? C33 C30 C29 C28 178.5(4) . . . . ? C52 C47 C48 C49 -2.7(6) . . . . ? C36 C47 C48 C49 177.8(4) . . . . ? C37 C42 C41 C40 2.2(6) . . . . ? O13 C42 C41 C40 177.5(4) . . . . ? C30 C29 C28 C27 0.8(7) . . . . ? C29 C30 C31 C32 0.9(6) . . . . ? C33 C30 C31 C32 -178.4(3) . . . . ? C29 C28 C27 C32 -1.1(7) . . . . ? C29 C28 C27 Cl2 179.0(4) . . . . ? C22 C23 C24 C25 -0.4(7) . . . . ? C22 C23 C24 N2 179.2(4) . . . . ? O8 N2 C24 C25 175.3(5) . . . . ? O7 N2 C24 C25 -3.4(7) . . . . ? O8 N2 C24 C23 -4.4(7) . . . . ? O7 N2 C24 C23 176.9(5) . . . . ? C24 C23 C22 C21 0.5(6) . . . . ? C26 C21 C22 C23 0.4(6) . . . . ? C10 C21 C22 C23 -178.0(4) . . . . ? C36 N3 C33 C38 -35.5(4) . . . . ? C36 N3 C33 C34 -152.7(3) . . . . ? C36 N3 C33 C30 82.9(3) . . . . ? C39 C38 C33 N3 -156.4(4) . . . . ? C37 C38 C33 N3 24.7(4) . . . . ? C39 C38 C33 C34 -41.6(5) . . . . ? C37 C38 C33 C34 139.6(3) . . . . ? C39 C38 C33 C30 84.4(5) . . . . ? C37 C38 C33 C30 -94.5(4) . . . . ? C31 C30 C33 N3 49.0(4) . . . . ? C29 C30 C33 N3 -130.2(4) . . . . ? C31 C30 C33 C38 160.6(3) . . . . ? C29 C30 C33 C38 -18.6(5) . . . . ? C31 C30 C33 C34 -73.6(4) . . . . ? C29 C30 C33 C34 107.2(4) . . . . ? C52 C51 C50 C49 0.6(6) . . . . ? C52 C51 C50 N4 179.9(3) . . . . ? O15 N4 C50 C51 -172.3(4) . . . . ? O16 N4 C50 C51 6.4(5) . . . . ? O15 N4 C50 C49 7.1(6) . . . . ? O16 N4 C50 C49 -174.3(4) . . . . ? C2 C1 C6 C5 -0.9(7) . . . . ? Cl1 C1 C6 C5 179.4(3) . . . . ? C1 C6 C5 C4 0.2(6) . . . . ? C3 C4 C5 C6 -0.1(6) . . . . ? C7 C4 C5 C6 -176.0(4) . . . . ? C12 C13 C14 C15 -1.4(6) . . . . ? O3 C13 C14 C15 174.5(4) . . . . ? C5 C4 C3 C2 0.6(6) . . . . ? C7 C4 C3 C2 176.2(4) . . . . ? C6 C1 C2 C3 1.3(7) . . . . ? Cl1 C1 C2 C3 -178.9(4) . . . . ? C4 C3 C2 C1 -1.2(6) . . . . ? C28 C27 C32 C31 1.3(6) . . . . ? Cl2 C27 C32 C31 -178.8(3) . . . . ? C30 C31 C32 C27 -1.2(6) . . . . ? C11 C16 C15 C14 2.7(6) . . . . ? O5 C16 C15 C14 177.0(4) . . . . ? C13 C14 C15 C16 -1.5(6) . . . . ? C42 C41 C40 C39 -2.7(6) . . . . ? C51 C50 C49 C48 0.7(6) . . . . ? N4 C50 C49 C48 -178.7(3) . . . . ? C47 C48 C49 C50 0.4(6) . . . . ? C7 N1 C10 C21 136.7(3) . . . . ? C7 N1 C10 C11 15.0(4) . . . . ? C26 C21 C10 N1 125.0(4) . . . . ? C22 C21 C10 N1 -56.7(5) . . . . ? C26 C21 C10 C11 -119.8(4) . . . . ? C22 C21 C10 C11 58.6(5) . . . . ? C12 C11 C10 N1 -5.9(4) . . . . ? C16 C11 C10 N1 172.9(4) . . . . ? C12 C11 C10 C21 -126.4(4) . . . . ? C16 C11 C10 C21 52.5(5) . . . . ? C22 C21 C26 C25 -1.4(6) . . . . ? C10 C21 C26 C25 177.0(4) . . . . ? C37 C38 C39 C40 3.3(6) . . . . ? C33 C38 C39 C40 -175.4(4) . . . . ? C37 C38 C39 O12 -170.3(3) . . . . ? C33 C38 C39 O12 11.0(6) . . . . ? C41 C40 C39 C38 -0.1(6) . . . . ? C41 C40 C39 O12 173.3(4) . . . . ? C43 O12 C39 C38 -131.0(4) . . . . ? C43 O12 C39 C40 55.5(5) . . . . ? C41 C42 C37 C38 1.1(6) . . . . ? O13 C42 C37 C38 -174.3(3) . . . . ? C41 C42 C37 C36 -178.3(4) . . . . ? O13 C42 C37 C36 6.4(6) . . . . ? C39 C38 C37 C42 -3.8(5) . . . . ? C33 C38 C37 C42 175.2(3) . . . . ? C39 C38 C37 C36 175.6(3) . . . . ? C33 C38 C37 C36 -5.4(4) . . . . ? N3 C36 C37 C42 163.1(4) . . . . ? C47 C36 C37 C42 43.6(5) . . . . ? N3 C36 C37 C38 -16.3(4) . . . . ? C47 C36 C37 C38 -135.8(3) . . . . ? C14 C13 C12 C11 3.2(6) . . . . ? O3 C13 C12 C11 -172.9(4) . . . . ? C14 C13 C12 C7 -174.7(4) . . . . ? O3 C13 C12 C7 9.3(6) . . . . ? C16 C11 C12 C13 -2.0(6) . . . . ? C10 C11 C12 C13 177.0(3) . . . . ? C16 C11 C12 C7 176.3(3) . . . . ? C10 C11 C12 C7 -4.8(4) . . . . ? N1 C7 C12 C13 -168.7(4) . . . . ? C4 C7 C12 C13 72.3(5) . . . . ? C8 C7 C12 C13 -54.9(5) . . . . ? N1 C7 C12 C11 13.2(4) . . . . ? C4 C7 C12 C11 -105.7(4) . . . . ? C8 C7 C12 C11 127.0(4) . . . . ? C23 C24 C25 C26 -0.6(7) . . . . ? N2 C24 C25 C26 179.8(4) . . . . ? C21 C26 C25 C24 1.5(7) . . . . ? C35 O9 C34 O10 0.5(6) . . . . ? C35 O9 C34 C33 -175.1(3) . . . . ? N3 C33 C34 O10 44.7(5) . . . . ? C38 C33 C34 O10 -64.9(5) . . . . ? C30 C33 C34 O10 169.4(4) . . . . ? N3 C33 C34 O9 -139.8(3) . . . . ? C38 C33 C34 O9 110.6(4) . . . . ? C30 C33 C34 O9 -15.1(4) . . . . ? C9 O2 C8 O1 5.4(6) . . . . ? C9 O2 C8 C7 -174.9(3) . . . . ? N1 C7 C8 O1 37.7(5) . . . . ? C4 C7 C8 O1 161.0(4) . . . . ? C12 C7 C8 O1 -71.6(5) . . . . ? N1 C7 C8 O2 -142.0(3) . . . . ? C4 C7 C8 O2 -18.8(5) . . . . ? C12 C7 C8 O2 108.6(4) . . . . ? C12 C13 O3 C19 -122.7(4) . . . . ? C14 C13 O3 C19 61.3(5) . . . . ? C42 O13 C45 O14 0.5(6) . . . . ? C42 O13 C45 C46 -179.6(3) . . . . ? C13 O3 C19 O4 1.5(7) . . . . ? C13 O3 C19 C20 -177.2(4) . . . . ? _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 62.83 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 0.215 _refine_diff_density_min -0.242 _refine_diff_density_rms 0.037