####################################################################### # # This file contains crystal structure data downloaded from the # Cambridge Structural Database (CSD) hosted by the Cambridge # Crystallographic Data Centre (CCDC). # # Full information about CCDC data access policies and citation # guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 # # Audit and citation data items may have been added by the CCDC. # Please retain this information to preserve the provenance of # this file and to allow appropriate attribution of the data. # ####################################################################### data_n1379 _audit_block_doi 10.5517/ccy42jn _database_code_depnum_ccdc_archive 'CCDC 867861' loop_ _citation_id _citation_doi _citation_year 1 10.1002/chem.201202070 2012 _audit_update_record ; 2012-02-20 deposited with the CCDC. 2016-10-08 downloaded from the CCDC. ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C76 H90 N10 O14 4(C2 F3 O2) 4(C2 H3 N)' _chemical_formula_sum 'C92 H102 F12 N14 O22' _chemical_formula_weight 1983.88 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' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.0829(8) _cell_length_b 14.6829(10) _cell_length_c 16.8532(17) _cell_angle_alpha 105.728(6) _cell_angle_beta 100.310(6) _cell_angle_gamma 110.620(4) _cell_volume 2353.3(3) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5934 _cell_measurement_theta_min 2.86 _cell_measurement_theta_max 64.30 _exptl_crystal_description plate _exptl_crystal_colour violet _exptl_crystal_size_max 0.57 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.400 _exptl_crystal_density_method ? _exptl_crystal_F_000 1036 _exptl_absorpt_coefficient_mu 0.995 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.6022 _exptl_absorpt_correction_T_max 0.9482 _exptl_absorpt_process_details 'XPREP, face-indexed' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source microsource _diffrn_radiation_monochromator 'Quazar optics' _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 16613 _diffrn_reflns_av_R_equivalents 0.1477 _diffrn_reflns_av_sigmaI/netI 0.1112 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.86 _diffrn_reflns_theta_max 64.94 _reflns_number_total 7680 _reflns_number_gt 5560 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Rigid bond restraints (esd 0.002) were imposed on the displacement parameters, as well as restraints on similar amplitudes (esd 0.002) separated by less than 1.7 Ang. on C27, C29, and N102. Distance restraints were refined on the bond between C28 and C29. ; _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^)+(0.1912P)^2^+4.8134P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7680 _refine_ls_number_parameters 633 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1349 _refine_ls_R_factor_gt 0.1101 _refine_ls_wR_factor_ref 0.3402 _refine_ls_wR_factor_gt 0.3102 _refine_ls_goodness_of_fit_ref 1.089 _refine_ls_restrained_S_all 1.096 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C -0.3373(4) -0.2086(3) -0.2547(3) 0.0229(10) Uani 1 1 d . . . H1 H -0.3820 -0.2827 -0.2795 0.027 Uiso 1 1 calc R . . C2 C -0.1956(4) -0.0511(3) -0.2602(3) 0.0215(10) Uani 1 1 d . . . H2 H -0.1401 -0.0147 -0.2886 0.026 Uiso 1 1 calc R . . C3 C -0.3583(4) -0.1574(3) -0.1814(3) 0.0213(9) Uani 1 1 d . . . H3 H -0.4168 -0.1960 -0.1558 0.026 Uiso 1 1 calc R . . C4 C -0.2146(4) 0.0039(3) -0.1873(3) 0.0180(9) Uani 1 1 d . . . H4 H -0.1736 0.0780 -0.1660 0.022 Uiso 1 1 calc R . . C5 C -0.2943(4) -0.0488(3) -0.1440(3) 0.0163(9) Uani 1 1 d . . . C6 C -0.3053(4) 0.0091(3) -0.0600(3) 0.0170(9) Uani 1 1 d . . . C7 C -0.3538(4) -0.0444(3) -0.0071(3) 0.0193(9) Uani 1 1 d . . . H7 H -0.3850 -0.1181 -0.0264 0.023 Uiso 1 1 calc R . . C8 C -0.2620(4) 0.1168(3) -0.0291(3) 0.0194(9) Uani 1 1 d . . . H8 H -0.2304 0.1553 -0.0640 0.023 Uiso 1 1 calc R . . C9 C -0.3563(4) 0.0094(3) 0.0725(3) 0.0218(10) Uani 1 1 d . . . H9 H -0.3904 -0.0276 0.1077 0.026 Uiso 1 1 calc R . . C10 C -0.2648(4) 0.1679(3) 0.0515(3) 0.0190(9) Uani 1 1 d . . . H10 H -0.2340 0.2416 0.0724 0.023 Uiso 1 1 calc R . . C11 C -0.3024(4) 0.1707(4) 0.1919(3) 0.0227(10) Uani 1 1 d . . . H11A H -0.3772 0.1277 0.2088 0.027 Uiso 1 1 calc R . . H11B H -0.3094 0.2371 0.1964 0.027 Uiso 1 1 calc R . . C12 C -0.1670(4) 0.1920(3) 0.2509(2) 0.0184(9) Uani 1 1 d . . . C13 C -0.1547(5) 0.1179(4) 0.2849(3) 0.0223(10) Uani 1 1 d . . . H13 H -0.2328 0.0589 0.2788 0.027 Uiso 1 1 calc R . . C14 C -0.0541(4) 0.2821(3) 0.2667(2) 0.0204(9) Uani 1 1 d . . . H14 H -0.0631 0.3352 0.2475 0.024 Uiso 1 1 calc R . . C15 C -0.0272(5) 0.1313(4) 0.3277(3) 0.0231(10) Uani 1 1 d . . . H15 H -0.0192 0.0806 0.3506 0.028 Uiso 1 1 calc R . . C16 C 0.0731(4) 0.2946(3) 0.3110(2) 0.0195(9) Uani 1 1 d . . . C17 C 0.0890(4) 0.2163(3) 0.3381(2) 0.0204(10) Uani 1 1 d . . . C18 C 0.2252(5) 0.2149(4) 0.3687(3) 0.0273(11) Uani 1 1 d . . . H18A H 0.2965 0.2872 0.3968 0.033 Uiso 1 1 calc R . . H18B H 0.2237 0.1802 0.4116 0.033 Uiso 1 1 calc R . . C19 C 0.2862(4) 0.4582(4) 0.3974(3) 0.0247(10) Uani 1 1 d . . . H19 H 0.3032 0.4532 0.4530 0.030 Uiso 1 1 calc R . . C20 C 0.3577(5) 0.5371(4) 0.3739(3) 0.0279(11) Uani 1 1 d . . . C21 C 0.4805(5) 0.6358(4) 0.4267(3) 0.0333(12) Uani 1 1 d . . . H21A H 0.4882 0.6869 0.3975 0.040 Uiso 1 1 calc R . . H21B H 0.4699 0.6656 0.4837 0.040 Uiso 1 1 calc R . . C22 C 0.6303(6) 0.5857(4) 0.3599(3) 0.0374(12) Uani 1 1 d . . . H22A H 0.6523 0.6416 0.3355 0.045 Uiso 1 1 calc R . . H22B H 0.5494 0.5242 0.3176 0.045 Uiso 1 1 calc R . . C23 C 0.7460(6) 0.5575(5) 0.3762(4) 0.0413(13) Uani 1 1 d . . . H23A H 0.7730 0.5406 0.3231 0.050 Uiso 1 1 calc R . . H23B H 0.8246 0.6169 0.4226 0.050 Uiso 1 1 calc R . . C24 C 0.7952(6) 0.4206(5) 0.3967(4) 0.0496(16) Uani 1 1 d . . . H24A H 0.8893 0.4743 0.4264 0.060 Uiso 1 1 calc R . . H24B H 0.7870 0.3874 0.3353 0.060 Uiso 1 1 calc R . . C25 C 0.7663(11) 0.3428(7) 0.4361(4) 0.074(3) Uani 1 1 d . . . H25A H 0.8372 0.3165 0.4378 0.089 Uiso 1 1 calc R . . H25B H 0.7691 0.3754 0.4965 0.089 Uiso 1 1 calc R . . C26 C 0.6441(8) 0.1838(7) 0.4342(5) 0.071(2) Uani 1 1 d . . . H26A H 0.7153 0.1600 0.4249 0.085 Uiso 1 1 calc R . . H26B H 0.6577 0.2137 0.4970 0.085 Uiso 1 1 calc R . . C27 C 0.5204(10) 0.1080(8) 0.3921(7) 0.125(5) Uani 1 1 d . . . H27A H 0.5220 0.0408 0.3913 0.150 Uiso 1 1 calc R . . H27B H 0.4964 0.1039 0.3313 0.150 Uiso 1 1 calc R . . C28 C 0.3730(9) 0.0886(7) 0.4988(5) 0.097(4) Uani 1 1 d D . . H28A H 0.4284 0.0506 0.5097 0.116 Uiso 1 1 calc R . . H28B H 0.4078 0.1526 0.5510 0.116 Uiso 1 1 calc R . . C29 C 0.2559(11) 0.033(2) 0.4964(8) 0.281(16) Uani 1 1 d D . . H29A H 0.2452 0.0690 0.5518 0.337 Uiso 1 1 calc R . . H29B H 0.2589 -0.0322 0.5000 0.337 Uiso 1 1 calc R . . C30 C 0.0569(12) -0.1026(9) 0.4169(5) 0.089(3) Uani 1 1 d . . . H30A H 0.0442 -0.1134 0.4708 0.107 Uiso 1 1 calc R . . H30B H 0.1035 -0.1448 0.3928 0.107 Uiso 1 1 calc R . . C31 C -0.0702(10) -0.1360(6) 0.3569(6) 0.083(3) Uani 1 1 d . . . H31A H -0.1307 -0.2064 0.3530 0.100 Uiso 1 1 calc R . . H31B H -0.1113 -0.0878 0.3776 0.100 Uiso 1 1 calc R . . C32 C -0.1964(9) -0.1774(5) 0.2168(5) 0.067(2) Uani 1 1 d . . . H32A H -0.2564 -0.2441 0.2195 0.080 Uiso 1 1 calc R . . H32B H -0.2342 -0.1258 0.2343 0.080 Uiso 1 1 calc R . . C33 C -0.1881(7) -0.1926(5) 0.1297(4) 0.0593(19) Uani 1 1 d . . . H33A H -0.2803 -0.2327 0.0880 0.071 Uiso 1 1 calc R . . H33B H -0.1354 -0.2340 0.1169 0.071 Uiso 1 1 calc R . . C34 C -0.0909(4) -0.0989(4) 0.0440(3) 0.0231(10) Uani 1 1 d . . . C35 C -0.1178(5) -0.1907(4) -0.0206(3) 0.0290(11) Uani 1 1 d . . . H35 H -0.1660 -0.2560 -0.0162 0.035 Uiso 1 1 calc R . . C36 C -0.0214(4) -0.0005(3) 0.0371(3) 0.0182(9) Uani 1 1 d . . . C37 C 0.0055(4) 0.0950(3) 0.1019(3) 0.0212(10) Uani 1 1 d . . . H37 H -0.0240 0.0948 0.1515 0.025 Uiso 1 1 calc R . . C38 C 0.0734(4) 0.1868(4) 0.0931(3) 0.0249(10) Uani 1 1 d . . . H38 H 0.0914 0.2503 0.1372 0.030 Uiso 1 1 calc R . . N1 N -0.2553(3) -0.1567(3) -0.2921(2) 0.0202(8) Uani 1 1 d . . . N2 N -0.3112(3) 0.1137(3) 0.1013(2) 0.0181(8) Uani 1 1 d . . . N3 N 0.1854(4) 0.3880(3) 0.3242(2) 0.0221(8) Uani 1 1 d . . . N4 N 0.1947(4) 0.4236(3) 0.2574(2) 0.0281(9) Uani 1 1 d . . . N5 N 0.2991(4) 0.5136(3) 0.2881(3) 0.0315(10) Uani 1 1 d . . . O1 O 0.6028(3) 0.6210(3) 0.4395(2) 0.0301(8) Uani 1 1 d . . . O2 O 0.7045(4) 0.4689(3) 0.4018(2) 0.0429(10) Uani 1 1 d . . . O3 O 0.6381(7) 0.2580(4) 0.3907(4) 0.0743(17) Uani 1 1 d . . . O4 O 0.4041(4) 0.1218(3) 0.4321(2) 0.0412(10) Uani 1 1 d . . . O5 O 0.1363(5) 0.0023(6) 0.4355(3) 0.0786(19) Uani 1 1 d . . . O6 O -0.0597(6) -0.1394(4) 0.2749(3) 0.0757(17) Uani 1 1 d . . . O7 O -0.1244(3) -0.0939(3) 0.1185(2) 0.0320(8) Uani 1 1 d . . . C101 C 0.6294(5) 0.3676(4) 0.1211(3) 0.0286(11) Uani 1 1 d . . . C102 C 0.5798(8) 0.4458(5) 0.1022(5) 0.066(2) Uani 1 1 d . . . C103 C 0.5077(5) 0.8961(4) 0.2466(3) 0.0342(12) Uani 1 1 d . . . C104 C 0.3819(8) 0.8078(6) 0.2433(5) 0.077(3) Uani 1 1 d . . . C105 C 0.0707(7) 0.4215(5) 0.0313(4) 0.0516(16) Uani 1 1 d . . . C106 C 0.2104(7) 0.4969(6) 0.0645(5) 0.066(2) Uani 1 1 d . . . H10A H 0.2627 0.4718 0.0303 0.099 Uiso 1 1 calc R . . H10B H 0.2471 0.5066 0.1251 0.099 Uiso 1 1 calc R . . H10C H 0.2161 0.5637 0.0606 0.099 Uiso 1 1 calc R . . C107 C 0.0569(7) 0.6249(7) 0.2999(5) 0.071(2) Uani 1 1 d . . . C108 C 0.0316(8) 0.5978(7) 0.2128(5) 0.077(2) Uani 1 1 d . . . H10D H 0.0994 0.5753 0.1954 0.115 Uiso 1 1 calc R . . H10E H 0.0360 0.6581 0.1969 0.115 Uiso 1 1 calc R . . H10F H -0.0588 0.5404 0.1833 0.115 Uiso 1 1 calc R . . O101 O 0.5421(4) 0.2774(3) 0.0882(3) 0.0463(10) Uani 1 1 d . . . O102 O 0.7472(4) 0.4014(3) 0.1666(3) 0.0485(11) Uani 1 1 d . . . O103 O 0.4882(4) 0.9389(3) 0.1955(2) 0.0356(9) Uani 1 1 d . . . O104 O 0.6107(4) 0.9176(3) 0.3029(3) 0.0517(11) Uani 1 1 d . . . F101 F 0.4877(8) 0.4530(7) 0.1408(4) 0.148(3) Uani 1 1 d . . . F102 F 0.5188(6) 0.4177(4) 0.0191(3) 0.105(2) Uani 1 1 d . . . F103 F 0.6733(8) 0.5407(3) 0.1298(5) 0.160(4) Uani 1 1 d . . . F104 F 0.2811(5) 0.7655(4) 0.1734(3) 0.098(2) Uani 1 1 d . . . F105 F 0.3328(8) 0.8406(9) 0.3070(4) 0.233(7) Uani 1 1 d . . . F106 F 0.4002(9) 0.7351(6) 0.2617(7) 0.224(6) Uani 1 1 d . . . N101 N -0.0392(7) 0.3613(5) 0.0045(4) 0.0715(19) Uani 1 1 d . . . N102 N 0.0774(10) 0.6479(13) 0.3716(6) 0.185(7) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.015(2) 0.023(2) 0.022(2) -0.0003(18) -0.0032(18) 0.0097(17) C2 0.021(2) 0.032(2) 0.012(2) 0.0047(17) -0.0022(17) 0.0168(19) C3 0.0099(19) 0.030(2) 0.021(2) 0.0059(18) -0.0007(17) 0.0104(17) C4 0.017(2) 0.027(2) 0.0111(19) 0.0045(16) -0.0012(16) 0.0157(18) C5 0.0087(18) 0.025(2) 0.0134(19) 0.0028(16) -0.0032(15) 0.0121(16) C6 0.0075(18) 0.031(2) 0.014(2) 0.0067(17) -0.0017(15) 0.0130(17) C7 0.0074(18) 0.029(2) 0.019(2) 0.0047(17) 0.0003(16) 0.0093(17) C8 0.0135(19) 0.028(2) 0.013(2) 0.0039(17) -0.0035(16) 0.0120(17) C9 0.013(2) 0.031(2) 0.020(2) 0.0072(18) 0.0012(17) 0.0105(18) C10 0.0112(19) 0.029(2) 0.018(2) 0.0066(17) 0.0025(16) 0.0122(17) C11 0.019(2) 0.038(2) 0.014(2) 0.0056(18) 0.0059(17) 0.0178(19) C12 0.019(2) 0.029(2) 0.0068(18) -0.0007(16) 0.0013(16) 0.0169(18) C13 0.024(2) 0.030(2) 0.013(2) 0.0023(17) 0.0047(18) 0.0159(19) C14 0.027(2) 0.027(2) 0.0079(19) -0.0015(16) 0.0012(17) 0.0200(19) C15 0.030(2) 0.034(2) 0.012(2) 0.0056(17) 0.0059(18) 0.023(2) C16 0.023(2) 0.028(2) 0.0057(18) -0.0018(16) 0.0027(16) 0.0154(19) C17 0.024(2) 0.032(2) 0.0063(18) -0.0012(16) 0.0008(16) 0.0209(19) C18 0.028(2) 0.040(3) 0.010(2) -0.0024(18) -0.0038(18) 0.025(2) C19 0.023(2) 0.034(2) 0.012(2) -0.0015(18) -0.0024(17) 0.017(2) C20 0.024(2) 0.031(2) 0.019(2) 0.0008(19) -0.0030(19) 0.011(2) C21 0.027(3) 0.034(3) 0.028(3) -0.001(2) 0.001(2) 0.014(2) C22 0.038(3) 0.046(3) 0.027(3) 0.011(2) 0.010(2) 0.018(2) C23 0.039(3) 0.054(3) 0.033(3) 0.012(3) 0.015(2) 0.022(3) C24 0.051(3) 0.061(4) 0.034(3) -0.002(3) 0.006(3) 0.038(3) C25 0.145(8) 0.082(5) 0.039(4) 0.023(4) 0.042(5) 0.090(6) C26 0.068(5) 0.096(6) 0.055(4) 0.020(4) 0.007(4) 0.053(5) C27 0.105(7) 0.115(7) 0.120(8) -0.033(6) -0.051(6) 0.106(7) C28 0.082(6) 0.105(6) 0.049(4) 0.052(4) -0.036(4) -0.012(5) C29 0.074(7) 0.62(4) 0.114(10) 0.252(18) 0.001(7) 0.029(14) C30 0.149(9) 0.141(9) 0.054(5) 0.065(5) 0.057(6) 0.113(8) C31 0.110(7) 0.062(5) 0.082(6) 0.050(4) 0.030(5) 0.021(5) C32 0.094(6) 0.046(4) 0.061(4) 0.021(3) 0.040(4) 0.021(4) C33 0.056(4) 0.048(4) 0.046(4) 0.013(3) 0.018(3) -0.007(3) C34 0.014(2) 0.035(2) 0.014(2) 0.0059(18) -0.0019(17) 0.0096(18) C35 0.025(2) 0.032(2) 0.021(2) 0.0050(19) -0.0033(19) 0.010(2) C36 0.0082(18) 0.030(2) 0.0130(19) 0.0013(17) -0.0030(15) 0.0125(17) C37 0.017(2) 0.032(2) 0.013(2) -0.0004(17) -0.0039(16) 0.0181(19) C38 0.024(2) 0.029(2) 0.016(2) -0.0031(18) -0.0035(18) 0.017(2) N1 0.0187(18) 0.032(2) 0.0087(16) -0.0003(14) -0.0050(14) 0.0193(16) N2 0.0109(16) 0.033(2) 0.0095(16) 0.0031(14) -0.0003(13) 0.0141(15) N3 0.0216(18) 0.030(2) 0.0120(17) -0.0001(15) -0.0016(14) 0.0163(16) N4 0.029(2) 0.029(2) 0.0150(18) 0.0034(16) -0.0032(16) 0.0089(17) N5 0.033(2) 0.032(2) 0.021(2) 0.0036(17) -0.0041(17) 0.0140(18) O1 0.0235(17) 0.0363(18) 0.0205(16) 0.0026(14) 0.0003(13) 0.0105(14) O2 0.054(2) 0.060(2) 0.031(2) 0.0152(18) 0.0199(18) 0.040(2) O3 0.137(5) 0.064(3) 0.083(4) 0.044(3) 0.084(4) 0.073(4) O4 0.0309(19) 0.049(2) 0.043(2) 0.0191(18) -0.0025(16) 0.0215(17) O5 0.045(3) 0.155(6) 0.048(3) 0.062(3) 0.024(2) 0.031(3) O6 0.093(4) 0.048(3) 0.058(3) 0.026(2) -0.016(3) 0.012(3) O7 0.0255(17) 0.045(2) 0.0179(16) 0.0091(14) 0.0051(14) 0.0090(15) C101 0.033(3) 0.030(3) 0.021(2) 0.0047(19) 0.011(2) 0.014(2) C102 0.082(5) 0.053(4) 0.047(4) 0.000(3) -0.010(4) 0.039(4) C103 0.041(3) 0.035(3) 0.021(2) 0.008(2) -0.002(2) 0.017(2) C104 0.073(5) 0.069(5) 0.048(4) 0.042(4) -0.023(4) -0.012(4) C105 0.055(4) 0.045(3) 0.055(4) 0.018(3) 0.001(3) 0.028(3) C106 0.057(4) 0.060(4) 0.070(5) 0.018(4) 0.001(4) 0.026(4) C107 0.041(4) 0.113(7) 0.059(5) 0.035(4) 0.016(3) 0.028(4) C108 0.057(4) 0.081(5) 0.061(5) 0.019(4) 0.011(4) 0.003(4) O101 0.033(2) 0.038(2) 0.060(3) 0.0192(19) 0.0048(19) 0.0098(17) O102 0.041(2) 0.038(2) 0.053(2) 0.0099(18) -0.0001(19) 0.0125(18) O103 0.038(2) 0.043(2) 0.0269(18) 0.0176(16) 0.0086(15) 0.0154(17) O104 0.043(2) 0.055(2) 0.045(2) 0.023(2) -0.0085(19) 0.0130(19) F101 0.159(6) 0.220(8) 0.099(4) 0.007(5) 0.016(4) 0.166(7) F102 0.148(5) 0.067(3) 0.074(3) 0.030(2) -0.031(3) 0.045(3) F103 0.177(7) 0.030(2) 0.180(6) 0.007(3) -0.087(5) 0.030(3) F104 0.073(3) 0.084(3) 0.072(3) 0.054(2) -0.037(2) -0.028(2) F105 0.132(6) 0.291(12) 0.076(4) 0.035(6) 0.034(4) -0.108(8) F106 0.161(7) 0.104(5) 0.286(11) 0.146(7) -0.127(7) -0.041(5) N101 0.063(4) 0.050(3) 0.082(4) 0.025(3) -0.013(3) 0.018(3) N102 0.077(6) 0.35(2) 0.072(6) 0.079(9) 0.015(5) 0.027(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.334(6) . ? C1 C3 1.367(6) . ? C1 H1 0.9500 . ? C2 N1 1.353(6) . ? C2 C4 1.371(6) . ? C2 H2 0.9500 . ? C3 C5 1.394(6) . ? C3 H3 0.9500 . ? C4 C5 1.403(6) . ? C4 H4 0.9500 . ? C5 C6 1.490(6) . ? C6 C8 1.390(6) . ? C6 C7 1.397(6) . ? C7 C9 1.371(6) . ? C7 H7 0.9500 . ? C8 C10 1.375(6) . ? C8 H8 0.9500 . ? C9 N2 1.342(6) . ? C9 H9 0.9500 . ? C10 N2 1.352(6) . ? C10 H10 0.9500 . ? C11 N2 1.497(5) . ? C11 C12 1.517(6) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C14 1.382(6) . ? C12 C13 1.396(6) . ? C13 C15 1.384(6) . ? C13 H13 0.9500 . ? C14 C16 1.395(6) . ? C14 H14 0.9500 . ? C15 C17 1.383(7) . ? C15 H15 0.9500 . ? C16 C17 1.400(6) . ? C16 N3 1.418(6) . ? C17 C18 1.515(6) . ? C18 N1 1.505(5) 2 ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 N3 1.356(5) . ? C19 C20 1.357(7) . ? C19 H19 0.9500 . ? C20 N5 1.366(6) . ? C20 C21 1.491(6) . ? C21 O1 1.435(6) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 O1 1.429(6) . ? C22 C23 1.484(8) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 O2 1.431(7) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 O2 1.420(7) . ? C24 C25 1.442(11) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 O3 1.416(11) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? C26 C27 1.331(12) . ? C26 O3 1.481(9) . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C27 O4 1.605(11) . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? C28 C29 1.252(12) . ? C28 O4 1.391(8) . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C29 O5 1.361(11) . ? C29 H29A 0.9900 . ? C29 H29B 0.9900 . ? C30 O5 1.388(12) . ? C30 C31 1.407(13) . ? C30 H30A 0.9900 . ? C30 H30B 0.9900 . ? C31 O6 1.396(10) . ? C31 H31A 0.9900 . ? C31 H31B 0.9900 . ? C32 C33 1.449(9) . ? C32 O6 1.464(10) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C33 O7 1.453(7) . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? C34 O7 1.362(5) . ? C34 C35 1.377(7) . ? C34 C36 1.425(7) . ? C35 C38 1.404(7) 2 ? C35 H35 0.9500 . ? C36 C36 1.417(9) 2 ? C36 C37 1.417(6) . ? C37 C38 1.356(7) . ? C37 H37 0.9500 . ? C38 C35 1.404(7) 2 ? C38 H38 0.9500 . ? N1 C18 1.505(5) 2 ? N3 N4 1.370(5) . ? N4 N5 1.300(6) . ? C101 O101 1.227(6) . ? C101 O102 1.232(6) . ? C101 C102 1.518(9) . ? C102 F103 1.301(9) . ? C102 F102 1.318(8) . ? C102 F101 1.324(11) . ? C103 O104 1.224(6) . ? C103 O103 1.227(6) . ? C103 C104 1.512(9) . ? C104 F106 1.260(10) . ? C104 F104 1.290(7) . ? C104 F105 1.341(14) . ? C105 N101 1.139(9) . ? C105 C106 1.443(10) . ? C106 H10A 0.9800 . ? C106 H10B 0.9800 . ? C106 H10C 0.9800 . ? C107 N102 1.118(11) . ? C107 C108 1.360(11) . ? C108 H10D 0.9800 . ? C108 H10E 0.9800 . ? C108 H10F 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 N1 C1 C3 121.3(4) . . ? N1 C1 H1 119.3 . . ? C3 C1 H1 119.3 . . ? N1 C2 C4 120.4(4) . . ? N1 C2 H2 119.8 . . ? C4 C2 H2 119.8 . . ? C1 C3 C5 120.4(4) . . ? C1 C3 H3 119.8 . . ? C5 C3 H3 119.8 . . ? C2 C4 C5 120.4(4) . . ? C2 C4 H4 119.8 . . ? C5 C4 H4 119.8 . . ? C3 C5 C4 116.9(4) . . ? C3 C5 C6 121.8(4) . . ? C4 C5 C6 121.2(4) . . ? C8 C6 C7 117.6(4) . . ? C8 C6 C5 122.4(4) . . ? C7 C6 C5 119.9(4) . . ? C9 C7 C6 120.1(4) . . ? C9 C7 H7 120.0 . . ? C6 C7 H7 120.0 . . ? C10 C8 C6 120.4(4) . . ? C10 C8 H8 119.8 . . ? C6 C8 H8 119.8 . . ? N2 C9 C7 120.9(4) . . ? N2 C9 H9 119.5 . . ? C7 C9 H9 119.5 . . ? N2 C10 C8 120.3(4) . . ? N2 C10 H10 119.8 . . ? C8 C10 H10 119.8 . . ? N2 C11 C12 107.7(3) . . ? N2 C11 H11A 110.2 . . ? C12 C11 H11A 110.2 . . ? N2 C11 H11B 110.2 . . ? C12 C11 H11B 110.2 . . ? H11A C11 H11B 108.5 . . ? C14 C12 C13 119.9(4) . . ? C14 C12 C11 120.0(4) . . ? C13 C12 C11 120.0(4) . . ? C15 C13 C12 119.2(4) . . ? C15 C13 H13 120.4 . . ? C12 C13 H13 120.4 . . ? C12 C14 C16 119.7(4) . . ? C12 C14 H14 120.2 . . ? C16 C14 H14 120.2 . . ? C17 C15 C13 122.1(4) . . ? C17 C15 H15 118.9 . . ? C13 C15 H15 118.9 . . ? C14 C16 C17 121.1(4) . . ? C14 C16 N3 117.0(4) . . ? C17 C16 N3 121.8(4) . . ? C15 C17 C16 117.5(4) . . ? C15 C17 C18 119.0(4) . . ? C16 C17 C18 123.2(4) . . ? N1 C18 C17 109.0(3) 2 . ? N1 C18 H18A 109.9 2 . ? C17 C18 H18A 109.9 . . ? N1 C18 H18B 109.9 2 . ? C17 C18 H18B 109.9 . . ? H18A C18 H18B 108.3 . . ? N3 C19 C20 105.0(4) . . ? N3 C19 H19 127.5 . . ? C20 C19 H19 127.5 . . ? C19 C20 N5 108.7(4) . . ? C19 C20 C21 129.7(4) . . ? N5 C20 C21 121.6(5) . . ? O1 C21 C20 113.0(4) . . ? O1 C21 H21A 109.0 . . ? C20 C21 H21A 109.0 . . ? O1 C21 H21B 109.0 . . ? C20 C21 H21B 109.0 . . ? H21A C21 H21B 107.8 . . ? O1 C22 C23 109.1(4) . . ? O1 C22 H22A 109.9 . . ? C23 C22 H22A 109.9 . . ? O1 C22 H22B 109.9 . . ? C23 C22 H22B 109.9 . . ? H22A C22 H22B 108.3 . . ? O2 C23 C22 108.0(5) . . ? O2 C23 H23A 110.1 . . ? C22 C23 H23A 110.1 . . ? O2 C23 H23B 110.1 . . ? C22 C23 H23B 110.1 . . ? H23A C23 H23B 108.4 . . ? O2 C24 C25 110.9(6) . . ? O2 C24 H24A 109.5 . . ? C25 C24 H24A 109.5 . . ? O2 C24 H24B 109.5 . . ? C25 C24 H24B 109.5 . . ? H24A C24 H24B 108.0 . . ? O3 C25 C24 112.1(6) . . ? O3 C25 H25A 109.2 . . ? C24 C25 H25A 109.2 . . ? O3 C25 H25B 109.2 . . ? C24 C25 H25B 109.2 . . ? H25A C25 H25B 107.9 . . ? C27 C26 O3 98.8(7) . . ? C27 C26 H26A 112.0 . . ? O3 C26 H26A 112.0 . . ? C27 C26 H26B 112.0 . . ? O3 C26 H26B 112.0 . . ? H26A C26 H26B 109.7 . . ? C26 C27 O4 114.9(7) . . ? C26 C27 H27A 108.5 . . ? O4 C27 H27A 108.5 . . ? C26 C27 H27B 108.5 . . ? O4 C27 H27B 108.5 . . ? H27A C27 H27B 107.5 . . ? C29 C28 O4 124.1(6) . . ? C29 C28 H28A 106.3 . . ? O4 C28 H28A 106.3 . . ? C29 C28 H28B 106.3 . . ? O4 C28 H28B 106.3 . . ? H28A C28 H28B 106.4 . . ? C28 C29 O5 128.7(9) . . ? C28 C29 H29A 105.1 . . ? O5 C29 H29A 105.1 . . ? C28 C29 H29B 105.1 . . ? O5 C29 H29B 105.1 . . ? H29A C29 H29B 105.9 . . ? O5 C30 C31 110.9(6) . . ? O5 C30 H30A 109.5 . . ? C31 C30 H30A 109.5 . . ? O5 C30 H30B 109.5 . . ? C31 C30 H30B 109.5 . . ? H30A C30 H30B 108.1 . . ? O6 C31 C30 111.7(8) . . ? O6 C31 H31A 109.3 . . ? C30 C31 H31A 109.3 . . ? O6 C31 H31B 109.3 . . ? C30 C31 H31B 109.3 . . ? H31A C31 H31B 107.9 . . ? C33 C32 O6 108.1(6) . . ? C33 C32 H32A 110.1 . . ? O6 C32 H32A 110.1 . . ? C33 C32 H32B 110.1 . . ? O6 C32 H32B 110.1 . . ? H32A C32 H32B 108.4 . . ? C32 C33 O7 111.8(5) . . ? C32 C33 H33A 109.3 . . ? O7 C33 H33A 109.3 . . ? C32 C33 H33B 109.3 . . ? O7 C33 H33B 109.3 . . ? H33A C33 H33B 107.9 . . ? O7 C34 C35 124.0(4) . . ? O7 C34 C36 115.2(4) . . ? C35 C34 C36 120.8(4) . . ? C34 C35 C38 119.3(5) . 2 ? C34 C35 H35 120.4 . . ? C38 C35 H35 120.4 2 . ? C36 C36 C37 119.6(5) 2 . ? C36 C36 C34 118.4(5) 2 . ? C37 C36 C34 121.9(4) . . ? C38 C37 C36 119.9(4) . . ? C38 C37 H37 120.1 . . ? C36 C37 H37 120.1 . . ? C37 C38 C35 122.0(4) . 2 ? C37 C38 H38 119.0 . . ? C35 C38 H38 119.0 2 . ? C1 N1 C2 120.4(4) . . ? C1 N1 C18 120.5(4) . 2 ? C2 N1 C18 119.1(4) . 2 ? C9 N2 C10 120.6(4) . . ? C9 N2 C11 119.3(4) . . ? C10 N2 C11 119.9(4) . . ? C19 N3 N4 110.0(4) . . ? C19 N3 C16 130.4(4) . . ? N4 N3 C16 119.3(3) . . ? N5 N4 N3 107.0(3) . . ? N4 N5 C20 109.4(4) . . ? C22 O1 C21 112.0(4) . . ? C24 O2 C23 111.2(5) . . ? C25 O3 C26 101.1(6) . . ? C28 O4 C27 123.6(7) . . ? C29 O5 C30 109.4(11) . . ? C31 O6 C32 107.8(7) . . ? C34 O7 C33 116.5(4) . . ? O101 C101 O102 129.2(5) . . ? O101 C101 C102 113.1(5) . . ? O102 C101 C102 117.7(5) . . ? F103 C102 F102 108.6(7) . . ? F103 C102 F101 104.9(7) . . ? F102 C102 F101 105.0(7) . . ? F103 C102 C101 114.3(6) . . ? F102 C102 C101 112.4(5) . . ? F101 C102 C101 111.0(7) . . ? O104 C103 O103 130.2(5) . . ? O104 C103 C104 115.4(5) . . ? O103 C103 C104 114.3(5) . . ? F106 C104 F104 107.4(7) . . ? F106 C104 F105 99.1(9) . . ? F104 C104 F105 105.1(9) . . ? F106 C104 C103 115.6(8) . . ? F104 C104 C103 117.1(5) . . ? F105 C104 C103 110.5(7) . . ? N101 C105 C106 179.3(9) . . ? C105 C106 H10A 109.5 . . ? C105 C106 H10B 109.5 . . ? H10A C106 H10B 109.5 . . ? C105 C106 H10C 109.5 . . ? H10A C106 H10C 109.5 . . ? H10B C106 H10C 109.5 . . ? N102 C107 C108 179.3(14) . . ? C107 C108 H10D 109.5 . . ? C107 C108 H10E 109.5 . . ? H10D C108 H10E 109.5 . . ? C107 C108 H10F 109.5 . . ? H10D C108 H10F 109.5 . . ? H10E C108 H10F 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 N1 C1 C3 C5 0.3(6) . . . . ? N1 C2 C4 C5 1.1(6) . . . . ? C1 C3 C5 C4 3.1(6) . . . . ? C1 C3 C5 C6 -174.6(4) . . . . ? C2 C4 C5 C3 -3.8(5) . . . . ? C2 C4 C5 C6 173.9(3) . . . . ? C3 C5 C6 C8 -168.8(4) . . . . ? C4 C5 C6 C8 13.6(5) . . . . ? C3 C5 C6 C7 14.7(5) . . . . ? C4 C5 C6 C7 -162.9(4) . . . . ? C8 C6 C7 C9 -0.6(5) . . . . ? C5 C6 C7 C9 176.0(3) . . . . ? C7 C6 C8 C10 1.4(5) . . . . ? C5 C6 C8 C10 -175.2(3) . . . . ? C6 C7 C9 N2 -0.7(6) . . . . ? C6 C8 C10 N2 -0.8(6) . . . . ? N2 C11 C12 C14 88.4(5) . . . . ? N2 C11 C12 C13 -87.7(5) . . . . ? C14 C12 C13 C15 -5.7(6) . . . . ? C11 C12 C13 C15 170.4(4) . . . . ? C13 C12 C14 C16 4.9(6) . . . . ? C11 C12 C14 C16 -171.2(4) . . . . ? C12 C13 C15 C17 0.2(6) . . . . ? C12 C14 C16 C17 1.4(6) . . . . ? C12 C14 C16 N3 179.1(3) . . . . ? C13 C15 C17 C16 5.9(6) . . . . ? C13 C15 C17 C18 -167.5(4) . . . . ? C14 C16 C17 C15 -6.7(6) . . . . ? N3 C16 C17 C15 175.7(4) . . . . ? C14 C16 C17 C18 166.4(4) . . . . ? N3 C16 C17 C18 -11.2(6) . . . . ? C15 C17 C18 N1 83.8(5) . . . 2 ? C16 C17 C18 N1 -89.3(5) . . . 2 ? N3 C19 C20 N5 0.2(5) . . . . ? N3 C19 C20 C21 -179.5(5) . . . . ? C19 C20 C21 O1 78.8(7) . . . . ? N5 C20 C21 O1 -100.9(6) . . . . ? O1 C22 C23 O2 66.1(5) . . . . ? O2 C24 C25 O3 65.4(6) . . . . ? O3 C26 C27 O4 -86.2(9) . . . . ? O4 C28 C29 O5 -7(4) . . . . ? O5 C30 C31 O6 69.5(9) . . . . ? O6 C32 C33 O7 -71.5(8) . . . . ? O7 C34 C35 C38 -177.1(4) . . . 2 ? C36 C34 C35 C38 1.4(6) . . . 2 ? O7 C34 C36 C36 177.6(4) . . . 2 ? C35 C34 C36 C36 -1.1(7) . . . 2 ? O7 C34 C36 C37 -2.5(6) . . . . ? C35 C34 C36 C37 178.9(4) . . . . ? C36 C36 C37 C38 -0.8(7) 2 . . . ? C34 C36 C37 C38 179.2(4) . . . . ? C36 C37 C38 C35 0.5(6) . . . 2 ? C3 C1 N1 C2 -3.1(6) . . . . ? C3 C1 N1 C18 175.3(4) . . . 2 ? C4 C2 N1 C1 2.4(6) . . . . ? C4 C2 N1 C18 -176.0(3) . . . 2 ? C7 C9 N2 C10 1.4(6) . . . . ? C7 C9 N2 C11 -173.8(3) . . . . ? C8 C10 N2 C9 -0.6(6) . . . . ? C8 C10 N2 C11 174.5(3) . . . . ? C12 C11 N2 C9 85.7(4) . . . . ? C12 C11 N2 C10 -89.6(4) . . . . ? C20 C19 N3 N4 -0.2(5) . . . . ? C20 C19 N3 C16 -174.0(4) . . . . ? C14 C16 N3 C19 129.4(5) . . . . ? C17 C16 N3 C19 -52.9(6) . . . . ? C14 C16 N3 N4 -43.9(5) . . . . ? C17 C16 N3 N4 133.8(4) . . . . ? C19 N3 N4 N5 0.2(5) . . . . ? C16 N3 N4 N5 174.8(4) . . . . ? N3 N4 N5 C20 -0.1(5) . . . . ? C19 C20 N5 N4 -0.1(6) . . . . ? C21 C20 N5 N4 179.7(4) . . . . ? C23 C22 O1 C21 -171.9(4) . . . . ? C20 C21 O1 C22 63.3(6) . . . . ? C25 C24 O2 C23 170.3(5) . . . . ? C22 C23 O2 C24 164.7(4) . . . . ? C24 C25 O3 C26 170.9(5) . . . . ? C27 C26 O3 C25 177.5(7) . . . . ? C29 C28 O4 C27 -129(2) . . . . ? C26 C27 O4 C28 -85.6(11) . . . . ? C28 C29 O5 C30 136(3) . . . . ? C31 C30 O5 C29 177.4(11) . . . . ? C30 C31 O6 C32 178.6(7) . . . . ? C33 C32 O6 C31 -173.5(6) . . . . ? C35 C34 O7 C33 2.2(7) . . . . ? C36 C34 O7 C33 -176.4(5) . . . . ? C32 C33 O7 C34 169.3(6) . . . . ? O101 C101 C102 F103 -174.2(7) . . . . ? O102 C101 C102 F103 6.5(10) . . . . ? O101 C101 C102 F102 -49.8(9) . . . . ? O102 C101 C102 F102 130.9(7) . . . . ? O101 C101 C102 F101 67.5(7) . . . . ? O102 C101 C102 F101 -111.9(7) . . . . ? O104 C103 C104 F106 -34.8(12) . . . . ? O103 C103 C104 F106 149.3(9) . . . . ? O104 C103 C104 F104 -163.1(8) . . . . ? O103 C103 C104 F104 21.0(11) . . . . ? O104 C103 C104 F105 76.7(10) . . . . ? O103 C103 C104 F105 -99.2(8) . . . . ? _diffrn_measured_fraction_theta_max 0.961 _diffrn_reflns_theta_full 64.94 _diffrn_measured_fraction_theta_full 0.961 _refine_diff_density_max 1.693 _refine_diff_density_min -0.992 _refine_diff_density_rms 0.109 # start Validation Reply Form _vrf_PLAT213_I ; PROBLEM: Atom C5 has ADP max/min Ratio ..... 5.1 oblat RESPONSE: The atoms of the glycol chain and of the CBPQT4+ ring showed elongated displacement parameters. Attempts to model this disorder did not significantly improve the refinement. ; _vrf_PLAT222_I ; PROBLEM: Large Non-Solvent H Uiso(max)/Uiso(min) .. 10.0 Ratio RESPONSE: Hydrogen atoms were refined as riding models with their isotropic displacement parameters linked to their parent atoms. In this case the parent atom exhibits disorder with an elongated displacement parameter and therefore the riding hydrogen atom is also large. ; _vrf_PLAT241_I ; PROBLEM: Check High Ueq as Compared to Neighbors for C27 RESPONSE: C27 and C29 are part of the disordered glycol chain, however they are bonded to C26 and O5 which are relatively well-ordered parts of the structure. ; # end Validation Reply Form