# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2001 # CCDC Number: 440/258 data_1 #------------------------------------------------------------------------- #2 Person making the deposition _publ_contact_author ; E. F. Paulus Hoechst Marion Roussel Deutschland GmbH, G864 D-65926 Frankfurt/Main, Germany present address: Institut fuer Mineralogie/Kristallographie der Johann Wolfgang Goethe-Universitaet Senckenberganlage 30, 60325 Frankfurt/Main, Germany ; _publ_contact_author_email e.paulus@kristall.uni-frankfurt.de #------------------------------------------------------------------------- # Publication details loop_ _publ_author_name ; Wojciech Wasikiewicz Faculty of Chemistry, Warsaw University of Technology ul. Noakowskiego 3,PL-00664 Warsaw, Poland ; ; Michal Slaski Faculty of Chemistry, Warsaw University of Technology ul. Noakowskiego 3,PL-00664 Warsaw, Poland ; ; Gabriel Rokicki Faculty of Chemistry, Warsaw University of Technology ul. Noakowskiego 3,PL-00664 Warsaw, Poland ; ; V. Boehmer Johannes Gutenberg-Universitaet, Fachbereich Chemie und Pharmazie, Abt. Lehramt Chemie, Duesbergweg 10-14, D-55099 Mainz, Germany ; ; Ch. Schmidt Johannes Gutenberg-Universitaet, Fachbereich Chemie und Pharmazie, Abt. Lehramt Chemie, Duesbergweg 10-14, D-55099 Mainz, Germany ; ; E. F. Paulus Hoechst Marion Roussel Deutschland GmbH, G864 D-65926 Frankfurt/Main, Germany present address: Institut fuer Mineralogie/Kristallographie der Johann Wolfgang Goethe-Universitaet Senckenberganlage 30, 60325 Frankfurt/Main, Germany ; _journal_name_full 'New J. Chem.' _journal_volume '?' _journal_page_first '?' _journal_page_last '?' _journal_year '?' _ccdc_journal_depnumber '?' #------------------------------------------------------------------------- #4 Chemical and physical data # Note that the units for melting point are Kelvin # The compound_id is the identifier for the compound in the published # paper, eg. 4a, II, etc. # Provide a brief description of any significant biological activity, # eg. antimalarial activity # If the compound exhibits polymorphism provide brief details, # eg. monoclinic form, low-temperature phase, etc. # For chemdiag include any ASCII file output by a chemical drawing # package # Against _type record, for example, ChemDraw # Against _records supply the chemical connectivity records _chemical_name_systematic ; 5,17-di-t-butyl-26,28-dihydroxy-25,27-(1,4,7,10,13,16-hexaoxa-hexadecano)- 11,23-(2-hydroxy-5-nitro-1,3-xyleno)-calix[4]arene ; _chemical_name_common '?' _chemical_formula_moiety ' C54H63NO11 x HCl3 ' _chemical_formula_sum ' C55H64Cl3NO11' _chemical_formula_weight '1021.42' _chemical_melting_point ? _ccdc_compound_id '?' _ccdc_biological_activity '?' _ccdc_polymorph '?' _ccdc_chemdiag_type '' _loop ; ; _exptl_crystal_density_diffrn '1.254' _exptl_crystal_colour '?' _diffrn_radiation_type 'Mo-K-alpha' _diffrn_measurement_device ; Bruker AXS three-circle-diffractometer with CCD and rotating anode ; _ccdc_temp_data_collection '293(2)' _ccdc_ls_R_squared '' _refine_ls_abs_structure_details '' _ccdc_disorder 'partial disorder' _ccdc_comments '' #------------------------------------------------------------------------- #6 Include your "standard" CIF file here # It should contain the following data items: # unit cell parameters and volume, z value, space group symbol, # R-factor(s), atomic coordinates with standard deviations, # occupancy factors, bond lengths and bond angles # Other data items may be present but will not necessarily be # included in the Cambridge Structural Database # Do not include structure factors data_sh455 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 5,17-di-t-butyl-26,28-dihydroxy-25,27-(1,4,7,10,13,16-hexaoxa-hexadecano)- 11,23-(2-hydroxy-5-nitro-1,3-xyleno)-calix[4]arene ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety Ç C54H63NO11 x HCl3' _chemical_formula_sum 'C55H64Cl3NO11' 'C55 H64 Cl3 N O11' _chemical_formula_weight 1021.42 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 ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 13.617(1) _cell_length_b 14.569(1) _cell_length_c 16.280(1) _cell_angle_alpha 64.67(1) _cell_angle_beta 84.612(1) _cell_angle_gamma 68.296(1) _cell_volume 2704.5(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used '9795' _cell_measurement_theta_min '1.61' _cell_measurement_theta_max '25.50' _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max '0.5mm' _exptl_crystal_size_mid '0.3mm' _exptl_crystal_size_min '0.2' _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.254 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1080 _exptl_absorpt_coefficient_mu 0.228 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source ; rotating anode, focus: 0.5 x 5 mm2, 50 kV 80 mA ; _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; Bruker AXS three circle diffractometer with CCD ; _diffrn_measurement_method 'omega-scan with steps of 0.3ƒ' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9795 _diffrn_reflns_av_R_equivalents 0.0187 _diffrn_reflns_av_sigmaI/netI 0.0606 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.61 _diffrn_reflns_theta_max 25.50 _reflns_number_total 8530 _reflns_number_gt 4087 _reflns_threshold_expression 2sigma(I) _computing_data_collection 'AXS-software' _computing_cell_refinement 'AXS-software' _computing_data_reduction 'AXS-software' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'AXS-software' _computing_publication_material 'AXS-software' _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^)+(0.1237P)^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 0.0151(18) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 8530 _refine_ls_number_parameters 786 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1130 _refine_ls_R_factor_gt 0.0644 _refine_ls_wR_factor_ref 0.2029 _refine_ls_wR_factor_gt 0.1757 _refine_ls_goodness_of_fit_ref 0.885 _refine_ls_restrained_S_all 0.887 _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 C01 C -0.4651(3) 1.0045(3) 0.1766(2) 0.0606(9) Uani 1 1 d . . . C02 C -0.4411(3) 0.9443(3) 0.1257(2) 0.0617(9) Uani 1 1 d . . . C03 C -0.3547(3) 0.9377(3) 0.0728(2) 0.0592(8) Uani 1 1 d . . . C04 C -0.2909(3) 0.9940(3) 0.0727(2) 0.0583(8) Uani 1 1 d . . . C05 C -0.3095(3) 1.0517(2) 0.1250(2) 0.0596(8) Uani 1 1 d . . . C06 C -0.3987(3) 1.0578(3) 0.1750(2) 0.0641(9) Uani 1 1 d . . . C07 C -0.3275(4) 0.8652(3) 0.0228(2) 0.0708(10) Uani 1 1 d . . . C08 C -0.3094(3) 0.7488(3) 0.0892(2) 0.0593(8) Uani 1 1 d . . . C09 C -0.3818(3) 0.7010(3) 0.0949(3) 0.0681(10) Uani 1 1 d . . . C10 C -0.3709(3) 0.5972(3) 0.1595(3) 0.0678(9) Uani 1 1 d . . . C11 C -0.2817(3) 0.5417(3) 0.2209(3) 0.0664(10) Uani 1 1 d . . . C12 C -0.2069(3) 0.5862(3) 0.2185(2) 0.0587(8) Uani 1 1 d . . . C13 C -0.2197(3) 0.6889(3) 0.1510(2) 0.0585(8) Uani 1 1 d . . . C14 C -0.1139(3) 0.5270(3) 0.2910(3) 0.0707(10) Uani 1 1 d . . . C15 C -0.1293(3) 0.5822(2) 0.3542(2) 0.0600(8) Uani 1 1 d . . . C16 C -0.2162(3) 0.5899(3) 0.4059(2) 0.0634(9) Uani 1 1 d . . . C17 C -0.2386(3) 0.6466(3) 0.4588(2) 0.0598(9) Uani 1 1 d . . . C18 C -0.1699(3) 0.6953(3) 0.4612(2) 0.0641(10) Uani 1 1 d . . . C19 C -0.0823(3) 0.6917(2) 0.4107(2) 0.0562(8) Uani 1 1 d . . . C20 C -0.0642(3) 0.6356(2) 0.3576(2) 0.0576(8) Uani 1 1 d . . . C21 C -0.0176(3) 0.7579(3) 0.4072(3) 0.0697(10) Uani 1 1 d . . . C22 C -0.0844(3) 0.8797(3) 0.3648(2) 0.0618(9) Uani 1 1 d . . . C23 C -0.1192(3) 0.9369(3) 0.4182(3) 0.0694(10) Uani 1 1 d . . . C24 C -0.1866(3) 1.0456(3) 0.3841(2) 0.0695(9) Uani 1 1 d . . . C25 C -0.2190(3) 1.0953(3) 0.2924(3) 0.0692(10) Uani 1 1 d . . . C26 C -0.1871(3) 1.0422(3) 0.2358(2) 0.0628(9) Uani 1 1 d . . . C27 C -0.1187(3) 0.9338(3) 0.2728(2) 0.0594(8) Uani 1 1 d . . . C28 C -0.2307(4) 1.0971(4) 0.1376(3) 0.0714(10) Uani 1 1 d . . . C29 C -0.5563(3) 1.0041(3) 0.2368(3) 0.0693(10) Uani 1 1 d . . . C30 C -0.4512(3) 0.5441(4) 0.1656(4) 0.0943(13) Uani 1 1 d . . . C31 C -0.4872(5) 0.5050(6) 0.2614(5) 0.164(3) Uani 1 1 d . . . H31A H -0.4264 0.4633 0.3046 0.246 Uiso 1 1 calc R . . H31B H -0.5269 0.4602 0.2677 0.246 Uiso 1 1 calc R . . H31C H -0.5312 0.5668 0.2724 0.246 Uiso 1 1 calc R . . C32 C -0.5464(5) 0.6204(5) 0.1013(6) 0.209(4) Uani 1 1 d . . . H32A H -0.5951 0.5842 0.1084 0.314 Uiso 1 1 calc R . . H32B H -0.5257 0.6430 0.0399 0.314 Uiso 1 1 calc R . . H32C H -0.5801 0.6831 0.1139 0.314 Uiso 1 1 calc R . . C33 C -0.3972(4) 0.4418(4) 0.1484(5) 0.143(2) Uani 1 1 d . . . H33A H -0.3331 0.3960 0.1874 0.214 Uiso 1 1 calc R . . H33B H -0.3807 0.4627 0.0859 0.214 Uiso 1 1 calc R . . H33C H -0.4441 0.4025 0.1611 0.214 Uiso 1 1 calc R . . C34 C -0.3406(3) 0.6625(3) 0.5070(2) 0.0694(10) Uani 1 1 d . . . C35 C -0.2259(4) 1.1057(4) 0.4438(3) 0.0942(13) Uani 1 1 d . . . C36 C -0.1812(6) 1.0390(5) 0.5409(4) 0.199(4) Uani 1 1 d . . . H36A H -0.1054 1.0070 0.5427 0.298 Uiso 1 1 calc R . . H36B H -0.2095 0.9823 0.5698 0.298 Uiso 1 1 calc R . . H36C H -0.2000 1.0850 0.5724 0.298 Uiso 1 1 calc R . . C37 C -0.3428(5) 1.1539(7) 0.4351(5) 0.218(4) Uani 1 1 d . . . H37A H -0.3667 1.1926 0.4727 0.327 Uiso 1 1 calc R . . H37B H -0.3708 1.0970 0.4541 0.327 Uiso 1 1 calc R . . H37C H -0.3670 1.2035 0.3726 0.327 Uiso 1 1 calc R . . C38 C -0.1903(7) 1.2040(5) 0.4072(5) 0.191(3) Uani 1 1 d . . . H38A H -0.2166 1.2444 0.4434 0.286 Uiso 1 1 calc R . . H38B H -0.2179 1.2504 0.3450 0.286 Uiso 1 1 calc R . . H38C H -0.1143 1.1786 0.4105 0.286 Uiso 1 1 calc R . . C39 C -0.4378(3) 0.7247(3) 0.4394(2) 0.0600(8) Uani 1 1 d . . . C40 C -0.5093(3) 0.6785(3) 0.4386(3) 0.0671(10) Uani 1 1 d . . . C41 C -0.5952(3) 0.7371(3) 0.3761(3) 0.0666(9) Uani 1 1 d . . . C42 C -0.6114(3) 0.8412(3) 0.3112(3) 0.0664(10) Uani 1 1 d . . . C43 C -0.5423(3) 0.8912(3) 0.3086(2) 0.0598(8) Uani 1 1 d . . . C44 C -0.4572(3) 0.8327(3) 0.3746(2) 0.0591(8) Uani 1 1 d . . . C45 C -0.2166(5) 1.0672(4) -0.0655(3) 0.0946(15) Uani 1 1 d . . . C46 C -0.1283(5) 1.0373(5) -0.1188(3) 0.1182(17) Uani 1 1 d . . . H46A H -0.1263 1.1014 -0.1717 0.177 Uiso 1 1 calc R . . H46B H -0.0615 1.0022 -0.0822 0.177 Uiso 1 1 calc R . . C47 C -0.0780(5) 0.9428(6) -0.2089(4) 0.147(2) Uani 1 1 d . . . H47A H -0.1042 1.0050 -0.2673 0.220 Uiso 1 1 calc R . . H47B H -0.0103 0.9409 -0.1925 0.220 Uiso 1 1 calc R . . C48 C -0.0587(7) 0.8545(6) -0.2218(4) 0.180(3) Uani 1 1 d . . . H48A H -0.0061 0.8534 -0.2663 0.270 Uiso 1 1 calc R . . H48B H -0.1233 0.8624 -0.2492 0.270 Uiso 1 1 calc R . . C49 C 0.0694(5) 0.6801(5) -0.1540(4) 0.1312(18) Uani 1 1 d . . . H49A H 0.1220 0.7140 -0.1729 0.197 Uiso 1 1 calc R . . H49B H 0.0604 0.6577 -0.2001 0.197 Uiso 1 1 calc R . . C50 C 0.1083(5) 0.5833(4) -0.0670(4) 0.1235(17) Uani 1 1 d . . . H50A H 0.0516 0.5556 -0.0452 0.185 Uiso 1 1 calc R . . H50B H 0.1658 0.5275 -0.0786 0.185 Uiso 1 1 calc R . . C51 C 0.0662(5) 0.6577(5) 0.0406(4) 0.141(2) Uani 1 1 d . . . H51A H 0.0170 0.6209 0.0684 0.211 Uiso 1 1 calc R . . H51B H 0.0267 0.7293 -0.0062 0.211 Uiso 1 1 calc R . . C52 C 0.1164(4) 0.6688(4) 0.1096(3) 0.1067(14) Uani 1 1 d . . . H52A H 0.1691 0.7009 0.0821 0.160 Uiso 1 1 calc R . . H52B H 0.0633 0.7182 0.1309 0.160 Uiso 1 1 calc R . . C53 C 0.1929(4) 0.5780(5) 0.2606(3) 0.0900(14) Uani 1 1 d . . . C54 C 0.1188(3) 0.5569(3) 0.3328(3) 0.0713(10) Uani 1 1 d . . . N1 N -0.6731(3) 0.6887(3) 0.3799(3) 0.0896(10) Uani 1 1 d . . . O01 O -0.20039(19) 0.98141(18) 0.02519(14) 0.0709(7) Uani 1 1 d . . . O02 O -0.14517(18) 0.73228(18) 0.14803(15) 0.0704(6) Uani 1 1 d . . . H02 H -0.1603 0.7919 0.1041 0.106 Uiso 1 1 calc R . . O03 O 0.01614(17) 0.64146(17) 0.29771(14) 0.0659(6) Uani 1 1 d . . . O04 O -0.0839(2) 0.88075(18) 0.21769(15) 0.0718(7) Uani 1 1 d . . . H04 H -0.1132 0.9209 0.1663 0.108 Uiso 1 1 calc R . . O05 O -0.7506(3) 0.7424(3) 0.3266(3) 0.1355(13) Uani 1 1 d . . . O06 O -0.6587(3) 0.5973(3) 0.4362(3) 0.1284(13) Uani 1 1 d . . . O07 O -0.3900(2) 0.8809(2) 0.37877(16) 0.0792(7) Uani 1 1 d . . . H07 H -0.3832 0.9224 0.3271 0.119 Uiso 1 1 calc R . . O08 O -0.1466(3) 0.9641(3) -0.1460(2) 0.1247(12) Uani 1 1 d . . . O09 O -0.0241(3) 0.7543(4) -0.1484(2) 0.1557(15) Uani 1 1 d . . . O10 O 0.1438(3) 0.5975(3) 0.0016(2) 0.1371(13) Uani 1 1 d . . . O11 O 0.1655(2) 0.5684(2) 0.1847(2) 0.1030(9) Uani 1 1 d . . . H02 H -0.482(2) 0.899(2) 0.1266(18) 0.054(8) Uiso 1 1 d . . . H06 H -0.413(3) 1.095(3) 0.216(2) 0.077(10) Uiso 1 1 d . . . H071 H -0.267(4) 0.865(4) -0.019(3) 0.137(18) Uiso 1 1 d . . . H072 H -0.385(3) 0.881(3) -0.014(3) 0.092(13) Uiso 1 1 d . . . H09 H -0.446(3) 0.743(3) 0.052(2) 0.074(10) Uiso 1 1 d . . . H11 H -0.273(3) 0.472(3) 0.264(2) 0.069(10) Uiso 1 1 d . . . H141 H -0.117(3) 0.450(3) 0.330(2) 0.074(10) Uiso 1 1 d . . . H142 H -0.053(3) 0.529(3) 0.260(2) 0.078(12) Uiso 1 1 d . . . H16 H -0.265(2) 0.556(2) 0.4035(19) 0.062(9) Uiso 1 1 d . . . H18 H -0.184(2) 0.735(2) 0.4911(19) 0.047(9) Uiso 1 1 d . . . H211 H 0.004(3) 0.738(3) 0.465(3) 0.082(12) Uiso 1 1 d . . . H212 H 0.048(3) 0.740(3) 0.375(2) 0.097(13) Uiso 1 1 d . . . H23 H -0.091(2) 0.896(2) 0.481(2) 0.051(8) Uiso 1 1 d . . . H25 H -0.259(3) 1.164(3) 0.268(2) 0.066(10) Uiso 1 1 d . . . H281 H -0.263(3) 1.173(3) 0.117(2) 0.069(10) Uiso 1 1 d . . . H282 H -0.174(3) 1.073(3) 0.102(2) 0.084(12) Uiso 1 1 d . . . H291 H -0.627(3) 1.030(3) 0.199(2) 0.073(10) Uiso 1 1 d . . . H292 H -0.565(2) 1.047(2) 0.2665(19) 0.054(9) Uiso 1 1 d . . . H341 H -0.343(3) 0.697(3) 0.550(2) 0.082(11) Uiso 1 1 d . . . H342 H -0.344(3) 0.586(3) 0.551(2) 0.083(10) Uiso 1 1 d . . . H40 H -0.498(3) 0.610(3) 0.480(2) 0.074(11) Uiso 1 1 d . . . H42 H -0.666(3) 0.874(3) 0.274(2) 0.063(11) Uiso 1 1 d . . . H451 H -0.287(4) 1.074(4) -0.110(3) 0.142(17) Uiso 1 1 d . . . H452 H -0.231(3) 1.125(3) -0.059(2) 0.086(14) Uiso 1 1 d . . . H531 H 0.258(4) 0.525(4) 0.287(3) 0.123(17) Uiso 1 1 d . . . H532 H 0.207(5) 0.646(6) 0.250(4) 0.21(3) Uiso 1 1 d . . . H541 H 0.109(3) 0.483(3) 0.350(2) 0.079(11) Uiso 1 1 d . . . H542 H 0.141(3) 0.563(3) 0.386(2) 0.079(11) Uiso 1 1 d . . . C1 C 0.2743(6) 0.3436(5) 0.1896(5) 0.144(2) Uani 1 1 d . A 1 H1 H 0.2409 0.4234 0.1617 0.216 Uiso 1 1 calc R A 1 Cl1 Cl 0.2738(4) 0.2961(2) 0.1125(2) 0.157(3) Uani 0.587(10) 1 d P A 1 Cl2 Cl 0.2000(4) 0.2857(4) 0.2843(3) 0.184(2) Uani 0.638(9) 1 d P A 1 Cl3 Cl 0.3930(4) 0.3062(7) 0.2365(9) 0.237(5) Uani 0.539(16) 1 d P A 1 Cl31 Cl 0.3868(10) 0.3276(7) 0.1106(8) 0.280(7) Uani 0.361(9) 1 d P B 2 Cl32 Cl 0.2037(17) 0.3045(11) 0.152(2) 0.56(2) Uani 0.461(13) 1 d P C 2 Cl33 Cl 0.360(2) 0.2865(11) 0.2757(10) 0.326(13) Uani 0.378(16) 1 d P D 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C01 0.058(2) 0.0520(18) 0.054(2) -0.0126(17) -0.0061(16) -0.0109(17) C02 0.065(2) 0.057(2) 0.056(2) -0.0171(18) -0.0102(18) -0.0197(18) C03 0.068(2) 0.0565(19) 0.0423(18) -0.0139(16) -0.0078(16) -0.0171(17) C04 0.065(2) 0.0522(18) 0.0447(18) -0.0137(16) 0.0001(16) -0.0149(17) C05 0.069(2) 0.0530(19) 0.0504(19) -0.0146(17) 0.0013(17) -0.0240(17) C06 0.077(3) 0.057(2) 0.055(2) -0.0231(18) 0.0042(19) -0.0220(19) C07 0.085(3) 0.072(2) 0.055(2) -0.027(2) -0.006(2) -0.025(2) C08 0.064(2) 0.060(2) 0.055(2) -0.0283(17) -0.0030(17) -0.0175(17) C09 0.061(2) 0.075(3) 0.074(3) -0.043(2) -0.006(2) -0.014(2) C10 0.057(2) 0.071(2) 0.087(3) -0.045(2) 0.0007(19) -0.0203(19) C11 0.070(2) 0.058(2) 0.077(3) -0.036(2) 0.006(2) -0.021(2) C12 0.057(2) 0.061(2) 0.063(2) -0.0352(18) 0.0004(16) -0.0148(17) C13 0.058(2) 0.064(2) 0.063(2) -0.0340(19) 0.0047(17) -0.0229(17) C14 0.066(3) 0.067(3) 0.077(3) -0.035(2) -0.009(2) -0.013(2) C15 0.058(2) 0.0537(19) 0.059(2) -0.0202(17) -0.0075(17) -0.0126(17) C16 0.066(2) 0.054(2) 0.064(2) -0.0189(18) -0.0083(19) -0.0202(18) C17 0.062(2) 0.0571(19) 0.0465(19) -0.0101(17) -0.0039(16) -0.0201(17) C18 0.075(3) 0.063(2) 0.050(2) -0.0226(19) -0.0078(18) -0.019(2) C19 0.053(2) 0.0544(18) 0.0531(19) -0.0167(17) -0.0073(16) -0.0156(16) C20 0.054(2) 0.0515(18) 0.0508(19) -0.0127(16) -0.0073(16) -0.0097(16) C21 0.064(2) 0.073(2) 0.074(3) -0.034(2) -0.002(2) -0.023(2) C22 0.057(2) 0.064(2) 0.070(2) -0.0307(19) 0.0007(17) -0.0247(17) C23 0.075(2) 0.075(2) 0.063(2) -0.031(2) -0.002(2) -0.027(2) C24 0.078(2) 0.070(2) 0.063(2) -0.032(2) 0.0070(19) -0.026(2) C25 0.077(3) 0.060(2) 0.070(3) -0.028(2) 0.004(2) -0.024(2) C26 0.075(2) 0.061(2) 0.060(2) -0.0243(19) 0.0078(18) -0.0339(19) C27 0.068(2) 0.064(2) 0.060(2) -0.0320(19) 0.0121(18) -0.0338(18) C28 0.094(3) 0.067(3) 0.062(2) -0.027(2) 0.013(2) -0.041(2) C29 0.062(2) 0.066(2) 0.071(2) -0.028(2) 0.006(2) -0.0152(19) C30 0.070(3) 0.094(3) 0.137(4) -0.062(3) 0.005(3) -0.033(2) C31 0.138(5) 0.203(7) 0.214(7) -0.111(6) 0.065(5) -0.114(5) C32 0.112(5) 0.153(5) 0.333(10) -0.044(6) -0.091(6) -0.062(4) C33 0.115(4) 0.145(5) 0.236(6) -0.125(5) 0.022(4) -0.069(4) C34 0.074(2) 0.075(3) 0.049(2) -0.015(2) 0.0022(18) -0.030(2) C35 0.111(4) 0.088(3) 0.076(3) -0.049(3) 0.000(2) -0.010(3) C36 0.280(9) 0.162(5) 0.101(4) -0.089(4) -0.030(5) 0.024(5) C37 0.126(5) 0.325(10) 0.222(7) -0.210(8) 0.023(5) 0.004(6) C38 0.309(10) 0.148(5) 0.167(6) -0.117(5) 0.032(6) -0.081(6) C39 0.062(2) 0.064(2) 0.0528(19) -0.0252(18) 0.0109(16) -0.0234(18) C40 0.069(3) 0.062(2) 0.071(3) -0.028(2) 0.016(2) -0.026(2) C41 0.059(2) 0.070(2) 0.083(3) -0.040(2) 0.014(2) -0.029(2) C42 0.052(2) 0.079(3) 0.070(3) -0.039(2) 0.003(2) -0.017(2) C43 0.052(2) 0.063(2) 0.062(2) -0.0265(18) 0.0074(17) -0.0183(17) C44 0.063(2) 0.063(2) 0.059(2) -0.0276(18) 0.0126(17) -0.0313(18) C45 0.140(5) 0.070(3) 0.062(3) -0.017(2) 0.026(3) -0.044(3) C46 0.155(5) 0.145(4) 0.076(3) -0.042(3) 0.035(3) -0.091(4) C47 0.160(6) 0.159(6) 0.083(4) -0.043(4) 0.036(4) -0.036(5) C48 0.231(8) 0.143(6) 0.090(4) -0.049(5) 0.014(4) 0.011(5) C49 0.137(5) 0.154(5) 0.108(4) -0.080(4) 0.019(4) -0.033(4) C50 0.156(5) 0.120(4) 0.094(4) -0.059(4) 0.011(3) -0.033(4) C51 0.137(5) 0.160(5) 0.111(4) -0.082(4) 0.002(4) -0.008(4) C52 0.117(4) 0.100(3) 0.089(3) -0.042(3) 0.003(3) -0.023(3) C53 0.058(3) 0.124(4) 0.085(3) -0.058(3) 0.003(2) -0.014(3) C54 0.055(2) 0.071(3) 0.069(3) -0.027(2) -0.0160(19) -0.0011(18) N1 0.078(2) 0.084(3) 0.122(3) -0.051(2) 0.009(2) -0.037(2) O01 0.0794(17) 0.0716(15) 0.0532(14) -0.0201(12) 0.0093(12) -0.0272(13) O02 0.0676(15) 0.0669(15) 0.0693(16) -0.0182(12) -0.0076(12) -0.0265(13) O03 0.0506(13) 0.0649(14) 0.0602(14) -0.0188(11) -0.0050(11) -0.0050(11) O04 0.0867(18) 0.0718(15) 0.0582(14) -0.0311(13) 0.0041(13) -0.0261(13) O05 0.099(2) 0.123(3) 0.185(4) -0.045(3) -0.035(3) -0.054(2) O06 0.106(2) 0.091(2) 0.185(3) -0.035(2) 0.002(2) -0.059(2) O07 0.0855(17) 0.0741(17) 0.0780(16) -0.0214(14) -0.0004(14) -0.0407(14) O08 0.158(3) 0.140(3) 0.088(2) -0.058(2) 0.050(2) -0.066(3) O09 0.156(4) 0.152(3) 0.094(3) -0.045(3) 0.011(2) 0.003(3) O10 0.122(3) 0.158(3) 0.117(3) -0.089(3) 0.006(2) 0.000(2) O11 0.122(2) 0.089(2) 0.0811(19) -0.0421(18) 0.0017(17) -0.0128(18) C1 0.143(6) 0.123(4) 0.186(7) -0.087(5) 0.011(5) -0.044(4) Cl1 0.234(6) 0.104(2) 0.107(2) -0.0585(16) 0.013(2) -0.018(2) Cl2 0.250(5) 0.226(4) 0.158(3) -0.111(3) 0.067(3) -0.151(3) Cl3 0.122(4) 0.250(7) 0.459(16) -0.250(9) 0.051(5) -0.083(4) Cl31 0.285(13) 0.223(8) 0.323(14) -0.145(8) 0.067(9) -0.062(8) Cl32 0.367(19) 0.316(14) 0.85(5) -0.018(17) -0.22(2) -0.179(13) Cl33 0.53(3) 0.215(9) 0.177(9) -0.112(7) -0.124(12) -0.010(13) _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 C01 C06 1.385(4) . ? C01 C02 1.386(5) . ? C01 C29 1.509(5) . ? C02 C03 1.390(4) . ? C02 H02 1.00(3) . ? C03 C04 1.398(4) . ? C03 C07 1.518(5) . ? C04 C05 1.381(4) . ? C04 O01 1.387(4) . ? C05 C06 1.394(5) . ? C05 C28 1.520(5) . ? C06 H06 1.00(3) . ? C07 C08 1.510(5) . ? C07 H071 1.02(5) . ? C07 H072 0.93(4) . ? C08 C09 1.378(5) . ? C08 C13 1.399(4) . ? C09 C10 1.385(5) . ? C09 H09 0.98(3) . ? C10 C11 1.392(5) . ? C10 C30 1.531(5) . ? C11 C12 1.384(5) . ? C11 H11 0.92(3) . ? C12 C13 1.384(4) . ? C12 C14 1.531(5) . ? C13 O02 1.367(4) . ? C14 C15 1.514(5) . ? C14 H141 1.04(3) . ? C14 H142 0.94(3) . ? C15 C16 1.384(5) . ? C15 C20 1.397(4) . ? C16 C17 1.375(5) . ? C16 H16 0.97(3) . ? C17 C18 1.379(5) . ? C17 C34 1.520(5) . ? C18 C19 1.382(5) . ? C18 H18 0.86(3) . ? C19 C20 1.376(4) . ? C19 C21 1.510(5) . ? C20 O03 1.397(4) . ? C21 C22 1.526(5) . ? C21 H211 0.90(4) . ? C21 H212 1.00(4) . ? C22 C23 1.388(5) . ? C22 C27 1.390(4) . ? C23 C24 1.388(5) . ? C23 H23 0.96(3) . ? C24 C25 1.382(5) . ? C24 C35 1.511(5) . ? C25 C26 1.386(5) . ? C25 H25 0.87(3) . ? C26 C27 1.388(4) . ? C26 C28 1.510(5) . ? C27 O04 1.368(4) . ? C28 H281 0.94(3) . ? C28 H282 0.97(4) . ? C29 C43 1.508(5) . ? C29 H291 1.05(3) . ? C29 H292 0.91(3) . ? C30 C32 1.486(7) . ? C30 C31 1.517(7) . ? C30 C33 1.532(6) . ? C31 H31A 0.9600 . ? C31 H31B 0.9600 . ? C31 H31C 0.9600 . ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 0.9600 . ? C33 H33A 0.9600 . ? C33 H33B 0.9600 . ? C33 H33C 0.9600 . ? C34 C39 1.522(5) . ? C34 H341 1.00(3) . ? C34 H342 1.06(3) . ? C35 C37 1.476(7) . ? C35 C36 1.497(6) . ? C35 C38 1.540(7) . ? C36 H36A 0.9600 . ? C36 H36B 0.9600 . ? C36 H36C 0.9600 . ? C37 H37A 0.9600 . ? C37 H37B 0.9600 . ? C37 H37C 0.9600 . ? C38 H38A 0.9600 . ? C38 H38B 0.9600 . ? C38 H38C 0.9600 . ? C39 C40 1.376(5) . ? C39 C44 1.409(4) . ? C40 C41 1.369(5) . ? C40 H40 0.89(3) . ? C41 C42 1.375(5) . ? C41 N1 1.460(5) . ? C42 C43 1.375(5) . ? C42 H42 0.85(3) . ? C43 C44 1.394(4) . ? C44 O07 1.365(4) . ? C45 O01 1.439(4) . ? C45 C46 1.459(7) . ? C45 H451 1.20(5) . ? C45 H452 0.84(4) . ? C46 O08 1.420(5) . ? C46 H46A 0.9700 . ? C46 H46B 0.9700 . ? C47 C48 1.319(8) . ? C47 O08 1.377(6) . ? C47 H47A 0.9700 . ? C47 H47B 0.9700 . ? C48 O09 1.373(7) . ? C48 H48A 0.9700 . ? C48 H48B 0.9700 . ? C49 O09 1.358(6) . ? C49 C50 1.467(7) . ? C49 H49A 0.9700 . ? C49 H49B 0.9700 . ? C50 O10 1.379(5) . ? C50 H50A 0.9700 . ? C50 H50B 0.9700 . ? C51 O10 1.397(6) . ? C51 C52 1.463(6) . ? C51 H51A 0.9700 . ? C51 H51B 0.9700 . ? C52 O11 1.407(5) . ? C52 H52A 0.9700 . ? C52 H52B 0.9700 . ? C53 O11 1.401(5) . ? C53 C54 1.479(6) . ? C53 H531 0.92(5) . ? C53 H532 1.02(7) . ? C54 O03 1.440(4) . ? C54 H541 1.05(3) . ? C54 H542 0.99(3) . ? N1 O06 1.203(4) . ? N1 O05 1.208(4) . ? O02 H02 0.8200 . ? O04 H04 0.8200 . ? O07 H07 0.8200 . ? C1 Cl3 1.648(10) . ? C1 Cl1 1.674(7) . ? C1 Cl2 1.827(8) . ? C1 H1 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 C06 C01 C02 118.0(3) . . ? C06 C01 C29 121.7(3) . . ? C02 C01 C29 120.2(3) . . ? C01 C02 C03 122.2(3) . . ? C01 C02 H02 123.2(16) . . ? C03 C02 H02 114.5(16) . . ? C02 C03 C04 117.6(3) . . ? C02 C03 C07 120.4(3) . . ? C04 C03 C07 121.9(3) . . ? C05 C04 O01 119.8(3) . . ? C05 C04 C03 122.2(3) . . ? O01 C04 C03 117.7(3) . . ? C04 C05 C06 117.8(3) . . ? C04 C05 C28 122.4(3) . . ? C06 C05 C28 119.4(3) . . ? C01 C06 C05 122.1(3) . . ? C01 C06 H06 117.4(19) . . ? C05 C06 H06 120.2(19) . . ? C08 C07 C03 110.4(3) . . ? C08 C07 H071 109(3) . . ? C03 C07 H071 119(3) . . ? C08 C07 H072 101(2) . . ? C03 C07 H072 112(2) . . ? H071 C07 H072 105(3) . . ? C09 C08 C13 118.4(3) . . ? C09 C08 C07 122.1(3) . . ? C13 C08 C07 119.4(3) . . ? C08 C09 C10 123.2(3) . . ? C08 C09 H09 119.3(19) . . ? C10 C09 H09 117.5(19) . . ? C09 C10 C11 116.3(3) . . ? C09 C10 C30 123.2(3) . . ? C11 C10 C30 120.5(4) . . ? C12 C11 C10 122.8(4) . . ? C12 C11 H11 120(2) . . ? C10 C11 H11 117(2) . . ? C11 C12 C13 118.8(3) . . ? C11 C12 C14 121.7(3) . . ? C13 C12 C14 119.4(3) . . ? O02 C13 C12 118.8(3) . . ? O02 C13 C08 120.8(3) . . ? C12 C13 C08 120.4(3) . . ? C15 C14 C12 110.8(3) . . ? C15 C14 H141 107.0(17) . . ? C12 C14 H141 105.1(18) . . ? C15 C14 H142 111(2) . . ? C12 C14 H142 107(2) . . ? H141 C14 H142 116(3) . . ? C16 C15 C20 116.8(3) . . ? C16 C15 C14 120.2(3) . . ? C20 C15 C14 122.8(3) . . ? C17 C16 C15 122.6(4) . . ? C17 C16 H16 117.9(17) . . ? C15 C16 H16 119.4(17) . . ? C16 C17 C18 118.0(3) . . ? C16 C17 C34 120.8(3) . . ? C18 C17 C34 121.1(3) . . ? C17 C18 C19 122.4(4) . . ? C17 C18 H18 120.4(19) . . ? C19 C18 H18 116.9(19) . . ? C20 C19 C18 117.4(3) . . ? C20 C19 C21 122.3(3) . . ? C18 C19 C21 120.0(3) . . ? C19 C20 O03 118.5(3) . . ? C19 C20 C15 122.7(3) . . ? O03 C20 C15 118.4(3) . . ? C19 C21 C22 110.9(3) . . ? C19 C21 H211 107(2) . . ? C22 C21 H211 109(2) . . ? C19 C21 H212 111(2) . . ? C22 C21 H212 112(2) . . ? H211 C21 H212 106(3) . . ? C23 C22 C27 118.4(3) . . ? C23 C22 C21 120.9(3) . . ? C27 C22 C21 120.5(3) . . ? C22 C23 C24 123.1(4) . . ? C22 C23 H23 115.0(17) . . ? C24 C23 H23 121.9(17) . . ? C25 C24 C23 116.1(3) . . ? C25 C24 C35 121.5(3) . . ? C23 C24 C35 122.3(3) . . ? C24 C25 C26 123.3(4) . . ? C24 C25 H25 119(2) . . ? C26 C25 H25 118(2) . . ? C25 C26 C27 118.5(3) . . ? C25 C26 C28 121.5(4) . . ? C27 C26 C28 119.9(3) . . ? O04 C27 C26 119.5(3) . . ? O04 C27 C22 120.0(3) . . ? C26 C27 C22 120.6(3) . . ? C26 C28 C05 110.9(3) . . ? C26 C28 H281 111.9(19) . . ? C05 C28 H281 110(2) . . ? C26 C28 H282 108(2) . . ? C05 C28 H282 102(2) . . ? H281 C28 H282 114(3) . . ? C43 C29 C01 112.3(3) . . ? C43 C29 H291 105.2(17) . . ? C01 C29 H291 110.9(17) . . ? C43 C29 H292 107.0(18) . . ? C01 C29 H292 112.6(19) . . ? H291 C29 H292 109(3) . . ? C32 C30 C31 108.2(5) . . ? C32 C30 C10 112.4(4) . . ? C31 C30 C10 110.1(4) . . ? C32 C30 C33 110.7(5) . . ? C31 C30 C33 105.9(5) . . ? C10 C30 C33 109.4(3) . . ? C30 C31 H31A 109.5 . . ? C30 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C30 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C30 C32 H32A 109.5 . . ? C30 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C30 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C30 C33 H33A 109.5 . . ? C30 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C30 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C17 C34 C39 111.5(3) . . ? C17 C34 H341 113(2) . . ? C39 C34 H341 112(2) . . ? C17 C34 H342 109.6(19) . . ? C39 C34 H342 107.8(18) . . ? H341 C34 H342 103(3) . . ? C37 C35 C36 112.8(5) . . ? C37 C35 C24 110.3(4) . . ? C36 C35 C24 113.8(4) . . ? C37 C35 C38 104.8(5) . . ? C36 C35 C38 106.0(5) . . ? C24 C35 C38 108.4(4) . . ? C35 C36 H36A 109.5 . . ? C35 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C35 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? C35 C37 H37A 109.5 . . ? C35 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? C35 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? C35 C38 H38A 109.5 . . ? C35 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? C35 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? C40 C39 C44 117.6(3) . . ? C40 C39 C34 122.0(3) . . ? C44 C39 C34 120.5(3) . . ? C41 C40 C39 120.1(4) . . ? C41 C40 H40 122(2) . . ? C39 C40 H40 118(2) . . ? C40 C41 C42 121.8(4) . . ? C40 C41 N1 119.1(4) . . ? C42 C41 N1 119.1(4) . . ? C43 C42 C41 120.6(4) . . ? C43 C42 H42 121(2) . . ? C41 C42 H42 118(2) . . ? C42 C43 C44 117.3(3) . . ? C42 C43 C29 121.8(3) . . ? C44 C43 C29 120.8(3) . . ? O07 C44 C43 119.8(3) . . ? O07 C44 C39 117.6(3) . . ? C43 C44 C39 122.5(3) . . ? O01 C45 C46 110.2(4) . . ? O01 C45 H451 112(2) . . ? C46 C45 H451 99(2) . . ? O01 C45 H452 106(3) . . ? C46 C45 H452 119(3) . . ? H451 C45 H452 111(4) . . ? O08 C46 C45 105.8(4) . . ? O08 C46 H46A 110.6 . . ? C45 C46 H46A 110.6 . . ? O08 C46 H46B 110.6 . . ? C45 C46 H46B 110.6 . . ? H46A C46 H46B 108.7 . . ? C48 C47 O08 121.0(6) . . ? C48 C47 H47A 107.1 . . ? O08 C47 H47A 107.1 . . ? C48 C47 H47B 107.1 . . ? O08 C47 H47B 107.1 . . ? H47A C47 H47B 106.8 . . ? C47 C48 O09 118.9(6) . . ? C47 C48 H48A 107.6 . . ? O09 C48 H48A 107.6 . . ? C47 C48 H48B 107.6 . . ? O09 C48 H48B 107.6 . . ? H48A C48 H48B 107.0 . . ? O09 C49 C50 112.4(5) . . ? O09 C49 H49A 109.1 . . ? C50 C49 H49A 109.1 . . ? O09 C49 H49B 109.1 . . ? C50 C49 H49B 109.1 . . ? H49A C49 H49B 107.9 . . ? O10 C50 C49 116.6(5) . . ? O10 C50 H50A 108.2 . . ? C49 C50 H50A 108.2 . . ? O10 C50 H50B 108.2 . . ? C49 C50 H50B 108.2 . . ? H50A C50 H50B 107.3 . . ? O10 C51 C52 109.6(5) . . ? O10 C51 H51A 109.8 . . ? C52 C51 H51A 109.8 . . ? O10 C51 H51B 109.8 . . ? C52 C51 H51B 109.8 . . ? H51A C51 H51B 108.2 . . ? O11 C52 C51 112.6(4) . . ? O11 C52 H52A 109.1 . . ? C51 C52 H52A 109.1 . . ? O11 C52 H52B 109.1 . . ? C51 C52 H52B 109.1 . . ? H52A C52 H52B 107.8 . . ? O11 C53 C54 111.8(4) . . ? O11 C53 H531 109(3) . . ? C54 C53 H531 105(3) . . ? O11 C53 H532 118(4) . . ? C54 C53 H532 111(4) . . ? H531 C53 H532 101(5) . . ? O03 C54 C53 107.9(3) . . ? O03 C54 H541 106.4(19) . . ? C53 C54 H541 112.0(18) . . ? O03 C54 H542 107(2) . . ? C53 C54 H542 110(2) . . ? H541 C54 H542 113(3) . . ? O06 N1 O05 122.2(4) . . ? O06 N1 C41 119.2(4) . . ? O05 N1 C41 118.6(4) . . ? C04 O01 C45 112.8(3) . . ? C13 O02 H02 109.5 . . ? C20 O03 C54 115.9(3) . . ? C27 O04 H04 109.5 . . ? C44 O07 H07 109.5 . . ? C47 O08 C46 111.7(4) . . ? C49 O09 C48 116.7(5) . . ? C50 O10 C51 116.1(4) . . ? C53 O11 C52 114.2(4) . . ? Cl3 C1 Cl1 114.2(5) . . ? Cl3 C1 Cl2 104.8(5) . . ? Cl1 C1 Cl2 108.4(4) . . ? Cl3 C1 H1 109.8 . . ? Cl1 C1 H1 109.8 . . ? Cl2 C1 H1 109.8 . . ? 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 C06 C01 C02 C03 -1.1(5) . . . . ? C29 C01 C02 C03 -176.7(3) . . . . ? C01 C02 C03 C04 0.4(4) . . . . ? C01 C02 C03 C07 176.2(3) . . . . ? C02 C03 C04 C05 2.1(4) . . . . ? C07 C03 C04 C05 -173.7(3) . . . . ? C02 C03 C04 O01 175.5(3) . . . . ? C07 C03 C04 O01 -0.2(4) . . . . ? O01 C04 C05 C06 -177.0(3) . . . . ? C03 C04 C05 C06 -3.7(5) . . . . ? O01 C04 C05 C28 -3.8(5) . . . . ? C03 C04 C05 C28 169.5(3) . . . . ? C02 C01 C06 C05 -0.6(5) . . . . ? C29 C01 C06 C05 174.9(3) . . . . ? C04 C05 C06 C01 2.9(5) . . . . ? C28 C05 C06 C01 -170.5(3) . . . . ? C02 C03 C07 C08 -57.4(4) . . . . ? C04 C03 C07 C08 118.2(4) . . . . ? C03 C07 C08 C09 106.7(4) . . . . ? C03 C07 C08 C13 -69.3(4) . . . . ? C13 C08 C09 C10 0.9(5) . . . . ? C07 C08 C09 C10 -175.1(3) . . . . ? C08 C09 C10 C11 0.6(5) . . . . ? C08 C09 C10 C30 -179.8(3) . . . . ? C09 C10 C11 C12 -0.2(5) . . . . ? C30 C10 C11 C12 -179.8(3) . . . . ? C10 C11 C12 C13 -1.6(5) . . . . ? C10 C11 C12 C14 175.5(3) . . . . ? C11 C12 C13 O02 -179.3(3) . . . . ? C14 C12 C13 O02 3.6(4) . . . . ? C11 C12 C13 C08 3.1(5) . . . . ? C14 C12 C13 C08 -174.0(3) . . . . ? C09 C08 C13 O02 179.6(3) . . . . ? C07 C08 C13 O02 -4.2(5) . . . . ? C09 C08 C13 C12 -2.8(5) . . . . ? C07 C08 C13 C12 173.4(3) . . . . ? C11 C12 C14 C15 -107.4(4) . . . . ? C13 C12 C14 C15 69.7(5) . . . . ? C12 C14 C15 C16 60.7(5) . . . . ? C12 C14 C15 C20 -113.3(4) . . . . ? C20 C15 C16 C17 -0.3(5) . . . . ? C14 C15 C16 C17 -174.7(3) . . . . ? C15 C16 C17 C18 -1.3(5) . . . . ? C15 C16 C17 C34 173.9(3) . . . . ? C16 C17 C18 C19 1.9(5) . . . . ? C34 C17 C18 C19 -173.3(3) . . . . ? C17 C18 C19 C20 -0.8(5) . . . . ? C17 C18 C19 C21 172.5(3) . . . . ? C18 C19 C20 O03 172.5(3) . . . . ? C21 C19 C20 O03 -0.7(4) . . . . ? C18 C19 C20 C15 -0.9(4) . . . . ? C21 C19 C20 C15 -174.1(3) . . . . ? C16 C15 C20 C19 1.5(4) . . . . ? C14 C15 C20 C19 175.7(3) . . . . ? C16 C15 C20 O03 -171.9(3) . . . . ? C14 C15 C20 O03 2.3(4) . . . . ? C20 C19 C21 C22 111.1(4) . . . . ? C18 C19 C21 C22 -61.9(5) . . . . ? C19 C21 C22 C23 106.2(4) . . . . ? C19 C21 C22 C27 -68.8(5) . . . . ? C27 C22 C23 C24 0.0(5) . . . . ? C21 C22 C23 C24 -175.0(3) . . . . ? C22 C23 C24 C25 0.5(5) . . . . ? C22 C23 C24 C35 178.4(4) . . . . ? C23 C24 C25 C26 -0.3(5) . . . . ? C35 C24 C25 C26 -178.1(4) . . . . ? C24 C25 C26 C27 -0.4(5) . . . . ? C24 C25 C26 C28 175.4(3) . . . . ? C25 C26 C27 O04 -178.2(3) . . . . ? C28 C26 C27 O04 5.9(5) . . . . ? C25 C26 C27 C22 1.0(5) . . . . ? C28 C26 C27 C22 -175.0(3) . . . . ? C23 C22 C27 O04 178.4(3) . . . . ? C21 C22 C27 O04 -6.6(5) . . . . ? C23 C22 C27 C26 -0.8(5) . . . . ? C21 C22 C27 C26 174.3(3) . . . . ? C25 C26 C28 C05 -105.8(4) . . . . ? C27 C26 C28 C05 70.0(5) . . . . ? C04 C05 C28 C26 -114.9(4) . . . . ? C06 C05 C28 C26 58.2(5) . . . . ? C06 C01 C29 C43 -115.6(4) . . . . ? C02 C01 C29 C43 59.9(4) . . . . ? C09 C10 C30 C32 -6.0(7) . . . . ? C11 C10 C30 C32 173.5(5) . . . . ? C09 C10 C30 C31 -126.7(5) . . . . ? C11 C10 C30 C31 52.9(5) . . . . ? C09 C10 C30 C33 117.3(5) . . . . ? C11 C10 C30 C33 -63.1(5) . . . . ? C16 C17 C34 C39 -60.5(4) . . . . ? C18 C17 C34 C39 114.5(4) . . . . ? C25 C24 C35 C37 52.7(7) . . . . ? C23 C24 C35 C37 -125.1(6) . . . . ? C25 C24 C35 C36 -179.3(5) . . . . ? C23 C24 C35 C36 3.0(7) . . . . ? C25 C24 C35 C38 -61.6(6) . . . . ? C23 C24 C35 C38 120.7(5) . . . . ? C17 C34 C39 C40 116.8(4) . . . . ? C17 C34 C39 C44 -62.8(4) . . . . ? C44 C39 C40 C41 0.3(5) . . . . ? C34 C39 C40 C41 -179.4(3) . . . . ? C39 C40 C41 C42 1.9(5) . . . . ? C39 C40 C41 N1 -176.5(3) . . . . ? C40 C41 C42 C43 -1.6(5) . . . . ? N1 C41 C42 C43 176.8(3) . . . . ? C41 C42 C43 C44 -0.9(5) . . . . ? C41 C42 C43 C29 178.4(3) . . . . ? C01 C29 C43 C42 -117.0(4) . . . . ? C01 C29 C43 C44 62.3(5) . . . . ? C42 C43 C44 O07 -175.9(3) . . . . ? C29 C43 C44 O07 4.8(5) . . . . ? C42 C43 C44 C39 3.1(5) . . . . ? C29 C43 C44 C39 -176.2(3) . . . . ? C40 C39 C44 O07 176.2(3) . . . . ? C34 C39 C44 O07 -4.2(4) . . . . ? C40 C39 C44 C43 -2.8(5) . . . . ? C34 C39 C44 C43 176.8(3) . . . . ? O01 C45 C46 O08 78.6(5) . . . . ? O08 C47 C48 O09 -54.7(10) . . . . ? O09 C49 C50 O10 -70.3(7) . . . . ? O10 C51 C52 O11 -65.9(6) . . . . ? O11 C53 C54 O03 -65.1(5) . . . . ? C40 C41 N1 O06 -2.1(5) . . . . ? C42 C41 N1 O06 179.4(4) . . . . ? C40 C41 N1 O05 177.3(4) . . . . ? C42 C41 N1 O05 -1.1(5) . . . . ? C05 C04 O01 C45 -90.4(4) . . . . ? C03 C04 O01 C45 96.0(4) . . . . ? C46 C45 O01 C04 -167.0(4) . . . . ? C19 C20 O03 C54 92.4(4) . . . . ? C15 C20 O03 C54 -93.9(4) . . . . ? C53 C54 O03 C20 -179.1(3) . . . . ? C48 C47 O08 C46 158.9(6) . . . . ? C45 C46 O08 C47 170.4(4) . . . . ? C50 C49 O09 C48 170.3(6) . . . . ? C47 C48 O09 C49 -123.1(7) . . . . ? C49 C50 O10 C51 70.9(7) . . . . ? C52 C51 O10 C50 -178.0(4) . . . . ? C54 C53 O11 C52 104.0(5) . . . . ? C51 C52 O11 C53 -166.1(4) . . . . ? _diffrn_measured_fraction_theta_max 0.846 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.846 _refine_diff_density_max 0.517 _refine_diff_density_min -0.254 _refine_diff_density_rms 0.046