# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 1999 # CCDC Number: 440/149 data_global _publ_requested_journal 'New Journal of Chemistry' _publ_contact_author 'Anderson Harry L., Dyson Perrins Lab.,South Parks Road, Oxford, OX1 3QY' _publ_contact_author_email Harry.Anderson@chem.ox.ac.uk _publ_section_title ; Water-soluble macrocyclic receptors for small neutral guests ; loop_ _publ_author_name 'Huuskonen, Juhani' 'Buston, Jonathan E.H.' 'Scotchmer, Neil D.' 'Anderson, Harry L.' _ccdc_compound_id 1 _ccdc_disorder ; Nitromethane C72 - O75 disordered over two sites with occupancies 0.65 and 0.35. Hexafluorophosphate P2 - F12 disordered over two sites with occupancies 0.65 and 0.35 ; data_1 _audit_creation_date 1999-05-11T13:22:20-00:00 #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; 1',1',1'',1''-Tetraethyl-5,9,13,15,21,25,29,31-tetramethoxydispiro[1,3,17,19- tetraoxa[3,1,3,1]paracyclophane-10,4':26,4''-bispiperdinium]dihexafluoro phosphate ; _chemical_formula_sum 'C54 H78 F12 N4 O16 P2' _chemical_formula_weight 1329.14 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.263(2) _cell_length_b 22.3356(13) _cell_length_c 22.566(2) _cell_angle_alpha 90 _cell_angle_beta 94.169(11) _cell_angle_gamma 90 _cell_volume 6164.3(13) _cell_formula_units_Z 4 _cell_measurement_temperature 183(2) #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour yellowish _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.25 _exptl_crystal_density_diffrn 1.432 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2784 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 1.57 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details ; North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351 ; _exptl_absorpt_correction_T_min 0.5384 _exptl_absorpt_correction_T_max 0.6949 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 183(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_monochromator graphite _diffrn_detector 'scintillation LiI' _diffrn_orient_matrix_type ; x-axis points to radiation source the matrix is specified in reciprocal space ; _diffrn_orient_matrix_ub_11 0.7987E-2 _diffrn_orient_matrix_ub_12 0.28456E-1 _diffrn_orient_matrix_ub_13 0.34247E-1 _diffrn_orient_matrix_ub_21 0.7627E-2 _diffrn_orient_matrix_ub_22 0.34019E-1 _diffrn_orient_matrix_ub_23 -0.28188E-1 _diffrn_orient_matrix_ub_31 -0.80989E-1 _diffrn_orient_matrix_ub_32 0.6042E-2 _diffrn_orient_matrix_ub_33 -0.2558E-2 _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_measurement_device_type 'Enraf Nonius MACH3' _diffrn_measurement_method 'non-profiled omega/2theta scans' _diffrn_standards_number 3 _diffrn_standards_interval_time 120 _diffrn_standards_decay_% 5 _diffrn_standards_decay_corr_max 1.102 _diffrn_standards_decay_corr_min 0.959 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l -3 10 0 -4 0 -8 5 4 -6 _diffrn_reflns_number 13167 _diffrn_reflns_av_R_equivalents 0.0416 _diffrn_reflns_av_sigmaI/netI 0.0676 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 2.79 _diffrn_reflns_theta_max 74.33 _diffrn_reflns_theta_full 74.33 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _reflns_number_total 12564 _reflns_number_gt 7357 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'CAD4 Express (Enraf Nonius, 1994)' _computing_cell_refinement 'CAD4 Express (Enraf Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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 _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_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.0005(3) _refine_ls_number_reflns 12564 _refine_ls_number_parameters 828 _refine_ls_number_restraints 116 _refine_ls_R_factor_all 0.1481 _refine_ls_R_factor_gt 0.0779 _refine_ls_wR_factor_ref 0.2486 _refine_ls_wR_factor_gt 0.2109 _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_restrained_S_all 3.583 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.861 _refine_diff_density_min -0.601 _refine_diff_density_rms 0.08 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.018 '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' P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 O1 O 0.2188(8) 0.2146(5) -0.0307(4) 0.039(2) Uani 1 1 d . . . O3 O 0.0756(8) 0.2697(4) -0.0730(5) 0.044(3) Uani 1 1 d . . . O13 O -0.4698(8) 0.0895(4) 0.1172(4) 0.036(2) Uani 1 1 d . . . O15 O -0.3168(8) 0.0818(5) 0.1821(4) 0.040(2) Uani 1 1 d . . . O51 O -0.0678(8) 0.2092(5) -0.1483(5) 0.045(3) Uani 1 1 d . . . O53 O 0.0058(10) 0.3394(6) 0.0104(6) 0.065(4) Uani 1 1 d . . . O55 O -0.4799(9) 0.2020(5) 0.1573(4) 0.043(2) Uani 1 1 d . . . O57 O -0.4281(10) 0.0670(4) 0.0041(4) 0.049(3) Uani 1 1 d . . . O59 O -0.1957(9) -0.0187(5) 0.1744(6) 0.053(3) Uani 1 1 d . . . O61 O -0.2244(10) 0.1885(5) 0.1810(8) 0.077(5) Uani 1 1 d . . . O63 O 0.2207(10) 0.2815(5) 0.0686(5) 0.047(3) Uani 1 1 d . . . N29 N -0.5989(9) 0.3493(5) -0.0702(5) 0.031(2) Uani 1 1 d . . . N42 N 0.3657(9) 0.0901(5) 0.2660(5) 0.035(3) Uani 1 1 d . . . C2 C 0.1290(12) 0.2134(6) -0.0736(6) 0.037(3) Uani 1 1 d . . . H2A H 0.0777 0.1812 -0.0642 0.044 Uiso 1 1 calc R . . H2B H 0.1546 0.2056 -0.1135 0.044 Uiso 1 1 calc R . . C4 C -0.0355(12) 0.2707(6) -0.0653(7) 0.037(3) Uani 1 1 d . . . C5 C -0.1116(12) 0.2407(7) -0.1036(6) 0.036(3) Uani 1 1 d . . . C6 C -0.2229(11) 0.2451(6) -0.0961(6) 0.035(3) Uani 1 1 d . . . H6 H -0.274 0.2241 -0.122 0.042 Uiso 1 1 calc R . . C7 C -0.2595(12) 0.2803(6) -0.0506(6) 0.033(3) Uani 1 1 d . . . C8 C -0.3828(11) 0.2833(6) -0.0394(6) 0.030(3) Uani 1 1 d . . . C9 C -0.4087(11) 0.2325(6) 0.0038(6) 0.033(3) Uani 1 1 d . . . C10 C -0.4308(11) 0.2429(6) 0.0623(6) 0.033(3) Uani 1 1 d . . . H10 H -0.4315 0.2828 0.0768 0.04 Uiso 1 1 calc R . . C11 C -0.4522(11) 0.1954(6) 0.1003(6) 0.034(3) Uani 1 1 d . . . C12 C -0.4475(11) 0.1368(6) 0.0801(6) 0.033(3) Uani 1 1 d . . . C14 C -0.3792(11) 0.0533(6) 0.1351(6) 0.035(3) Uani 1 1 d . . . H14A H -0.3336 0.0469 0.1012 0.041 Uiso 1 1 calc R . . H14B H -0.4048 0.0138 0.1484 0.041 Uiso 1 1 calc R . . C16 C -0.2048(11) 0.0848(6) 0.1785(6) 0.032(3) Uani 1 1 d . . . C17 C -0.1401(12) 0.0341(6) 0.1779(6) 0.034(3) Uani 1 1 d . . . C18 C -0.0257(11) 0.0386(6) 0.1811(6) 0.035(3) Uani 1 1 d . . . H18 H 0.0179 0.0036 0.1797 0.042 Uiso 1 1 calc R . . C19 C 0.0234(11) 0.0944(6) 0.1864(6) 0.031(3) Uani 1 1 d . . . C20 C 0.1485(11) 0.1024(6) 0.1914(6) 0.031(3) Uani 1 1 d . . . C21 C 0.1775(10) 0.1321(6) 0.1328(6) 0.030(3) Uani 1 1 d . . . C22 C 0.1910(11) 0.1942(6) 0.1291(6) 0.033(3) Uani 1 1 d . . . H22 H 0.1908 0.2178 0.1641 0.04 Uiso 1 1 calc R . . C23 C 0.2047(12) 0.2217(6) 0.0750(6) 0.035(3) Uani 1 1 d . . . C24 C 0.2043(11) 0.1878(7) 0.0234(6) 0.034(3) Uani 1 1 d . . . C25 C -0.0724(12) 0.3077(7) -0.0218(7) 0.043(4) Uani 1 1 d . . . C26 C -0.1847(12) 0.3114(7) -0.0134(7) 0.041(3) Uani 1 1 d . . . H26 H -0.2093 0.3353 0.0178 0.049 Uiso 1 1 calc R . . C27 C -0.4106(12) 0.3465(6) -0.0157(6) 0.033(3) Uani 1 1 d . . . H27A H -0.3731 0.3515 0.0244 0.04 Uiso 1 1 calc R . . H27B H -0.381 0.377 -0.042 0.04 Uiso 1 1 calc R . . C28 C -0.5316(12) 0.3582(6) -0.0117(6) 0.035(3) Uani 1 1 d . . . H28A H -0.5414 0.3999 0.002 0.042 Uiso 1 1 calc R . . H28B H -0.5595 0.3311 0.0185 0.042 Uiso 1 1 calc R . . C30 C -0.5747(12) 0.2871(6) -0.0919(6) 0.034(3) Uani 1 1 d . . . H30A H -0.6159 0.2805 -0.1308 0.041 Uiso 1 1 calc R . . H30B H -0.6007 0.2575 -0.0636 0.041 Uiso 1 1 calc R . . C31 C -0.4533(11) 0.2767(6) -0.0988(6) 0.032(3) Uani 1 1 d . . . H31A H -0.4277 0.3058 -0.1279 0.038 Uiso 1 1 calc R . . H31B H -0.4431 0.236 -0.1148 0.038 Uiso 1 1 calc R . . C32 C -0.7193(12) 0.3510(7) -0.0585(7) 0.040(3) Uani 1 1 d . . . H32A H -0.7625 0.339 -0.0954 0.048 Uiso 1 1 calc R . . H32B H -0.7325 0.3208 -0.0278 0.048 Uiso 1 1 calc R . . C33 C -0.7617(15) 0.4101(8) -0.0387(9) 0.056(4) Uani 1 1 d . . . H33A H -0.8396 0.4065 -0.0323 0.085 Uiso 1 1 calc R . . H33B H -0.7518 0.4403 -0.0694 0.085 Uiso 1 1 calc R . . H33C H -0.7213 0.4222 -0.0016 0.085 Uiso 1 1 calc R . . C34 C -0.5716(12) 0.3967(6) -0.1137(6) 0.037(3) Uani 1 1 d . . . H34A H -0.493 0.3934 -0.1206 0.044 Uiso 1 1 calc R . . H34B H -0.5832 0.4364 -0.0957 0.044 Uiso 1 1 calc R . . C35 C -0.6367(16) 0.3939(9) -0.1728(7) 0.060(5) Uani 1 1 d . . . H35A H -0.6135 0.4263 -0.1983 0.089 Uiso 1 1 calc R . . H35B H -0.7146 0.3984 -0.1668 0.089 Uiso 1 1 calc R . . H35C H -0.6244 0.3553 -0.1917 0.089 Uiso 1 1 calc R . . C36 C -0.4072(12) 0.1732(6) -0.0167(6) 0.037(3) Uani 1 1 d . . . H36 H -0.3924 0.1652 -0.0567 0.045 Uiso 1 1 calc R . . C37 C -0.4272(12) 0.1265(6) 0.0208(6) 0.037(3) Uani 1 1 d . . . C38 C -0.1550(12) 0.1410(7) 0.1814(7) 0.042(4) Uani 1 1 d . . . C39 C -0.0419(12) 0.1452(6) 0.1850(7) 0.041(3) Uani 1 1 d . . . H39 H -0.0085 0.1836 0.1864 0.05 Uiso 1 1 calc R . . C40 C 0.1819(11) 0.1409(6) 0.2470(6) 0.033(3) Uani 1 1 d . . . H40A H 0.1473 0.1808 0.2423 0.039 Uiso 1 1 calc R . . H40B H 0.1536 0.1217 0.2824 0.039 Uiso 1 1 calc R . . C41 C 0.3048(11) 0.1487(6) 0.2576(6) 0.033(3) Uani 1 1 d . . . H41A H 0.3323 0.1701 0.2233 0.04 Uiso 1 1 calc R . . H41B H 0.3204 0.1738 0.2933 0.04 Uiso 1 1 calc R . . C43 C 0.3316(11) 0.0498(7) 0.2136(6) 0.037(3) Uani 1 1 d . . . H43A H 0.3652 0.0099 0.2206 0.044 Uiso 1 1 calc R . . H43B H 0.3608 0.0667 0.1774 0.044 Uiso 1 1 calc R . . C44 C 0.2084(11) 0.0422(6) 0.2025(6) 0.033(3) Uani 1 1 d . . . H44A H 0.1796 0.0223 0.2373 0.04 Uiso 1 1 calc R . . H44B H 0.193 0.0158 0.1676 0.04 Uiso 1 1 calc R . . C45 C 0.4880(11) 0.1016(7) 0.2632(7) 0.041(3) Uani 1 1 d . . . H45A H 0.5262 0.0625 0.2649 0.049 Uiso 1 1 calc R . . H45B H 0.4998 0.1199 0.2243 0.049 Uiso 1 1 calc R . . C46 C 0.5405(14) 0.1414(9) 0.3115(8) 0.058(5) Uani 1 1 d . . . H46A H 0.6185 0.146 0.3057 0.087 Uiso 1 1 calc R . . H46B H 0.5318 0.1232 0.3504 0.087 Uiso 1 1 calc R . . H46C H 0.5051 0.1807 0.3097 0.087 Uiso 1 1 calc R . . C47 C 0.3417(14) 0.0634(8) 0.3259(7) 0.050(4) Uani 1 1 d . . . H47A H 0.3532 0.0949 0.3565 0.06 Uiso 1 1 calc R . . H47B H 0.2636 0.0519 0.3242 0.06 Uiso 1 1 calc R . . C48 C 0.4074(18) 0.0110(9) 0.3451(9) 0.067(5) Uani 1 1 d . . . H48A H 0.3859 -0.0026 0.3838 0.101 Uiso 1 1 calc R . . H48B H 0.485 0.0219 0.3483 0.101 Uiso 1 1 calc R . . H48C H 0.3951 -0.0212 0.3159 0.101 Uiso 1 1 calc R . . C49 C 0.1828(12) 0.0984(6) 0.0813(6) 0.035(3) Uani 1 1 d . . . H49 H 0.1768 0.0561 0.0832 0.042 Uiso 1 1 calc R . . C52 C -0.1402(14) 0.1724(8) -0.1852(8) 0.051(4) Uani 1 1 d . . . H52A H -0.0989 0.1523 -0.2151 0.076 Uiso 1 1 calc R . . H52B H -0.1975 0.1973 -0.2051 0.076 Uiso 1 1 calc R . . H52C H -0.1737 0.1423 -0.1607 0.076 Uiso 1 1 calc R . . C54 C -0.0311(17) 0.3846(11) 0.0493(11) 0.084(7) Uani 1 1 d . . . H54A H 0.0322 0.4044 0.0699 0.125 Uiso 1 1 calc R . . H54B H -0.0757 0.3661 0.0787 0.125 Uiso 1 1 calc R . . H54C H -0.075 0.4142 0.0261 0.125 Uiso 1 1 calc R . . C56 C -0.4910(17) 0.2613(8) 0.1787(8) 0.059(5) Uani 1 1 d . . . H56A H -0.511 0.2601 0.22 0.088 Uiso 1 1 calc R . . H56B H -0.5481 0.2822 0.1541 0.088 Uiso 1 1 calc R . . H56C H -0.4215 0.2826 0.1769 0.088 Uiso 1 1 calc R . . C58 C -0.423(2) 0.0544(8) -0.0579(8) 0.071(6) Uani 1 1 d . . . H58A H -0.4244 0.011 -0.0642 0.106 Uiso 1 1 calc R . . H58B H -0.3561 0.0712 -0.0719 0.106 Uiso 1 1 calc R . . H58C H -0.4868 0.0725 -0.0802 0.106 Uiso 1 1 calc R . . C60 C -0.1327(17) -0.0729(8) 0.1697(11) 0.071(6) Uani 1 1 d . . . H60A H -0.1821 -0.1075 0.1676 0.107 Uiso 1 1 calc R . . H60B H -0.0807 -0.0768 0.2045 0.107 Uiso 1 1 calc R . . H60C H -0.0928 -0.0714 0.1336 0.107 Uiso 1 1 calc R . . C64 C 0.1982(17) 0.3189(8) 0.1181(8) 0.059(5) Uani 1 1 d . . . H64A H 0.2126 0.3608 0.1085 0.088 Uiso 1 1 calc R . . H64B H 0.2453 0.307 0.1531 0.088 Uiso 1 1 calc R . . H64C H 0.1214 0.3143 0.1266 0.088 Uiso 1 1 calc R . . C62 C -0.177(2) 0.2458(9) 0.176(2) 0.18(2) Uani 1 1 d . . . H62A H -0.234 0.2764 0.1764 0.277 Uiso 1 1 calc R . . H62B H -0.1404 0.2483 0.1391 0.277 Uiso 1 1 calc R . . H62C H -0.1232 0.2523 0.2099 0.277 Uiso 1 1 calc R . . C50 C 0.1967(12) 0.1258(6) 0.0278(5) 0.037(3) Uani 1 1 d D A . O65 O 0.1998(10) 0.0933(5) -0.0238(4) 0.052(3) Uani 1 1 d D . . C66 C 0.3073(18) 0.0829(16) -0.0424(13) 0.079(9) Uani 0.654(10) 1 d PD A 1 H66A H 0.3023 0.0594 -0.0792 0.119 Uiso 0.654(10) 1 calc PR A 1 H66B H 0.3504 0.0607 -0.0113 0.119 Uiso 0.654(10) 1 calc PR A 1 H66C H 0.3428 0.1213 -0.0493 0.119 Uiso 0.654(10) 1 calc PR A 1 C66' C 0.217(6) 0.0305(10) -0.019(2) 0.079(9) Uani 0.346(10) 1 d PD A 2 H66D H 0.2169 0.013 -0.059 0.119 Uiso 0.346(10) 1 calc PR A 2 H66E H 0.1591 0.0123 0.0023 0.119 Uiso 0.346(10) 1 calc PR A 2 H66F H 0.2882 0.0228 0.0025 0.119 Uiso 0.346(10) 1 calc PR A 2 P1 P 0.0353(4) 0.35996(18) 0.27075(17) 0.0428(10) Uani 1 1 d . . . F1 F 0.1018(9) 0.3570(5) 0.3339(4) 0.059(3) Uani 1 1 d . . . F2 F -0.0027(9) 0.4267(4) 0.2845(5) 0.063(3) Uani 1 1 d . . . F3 F -0.0282(10) 0.3621(5) 0.2073(5) 0.077(3) Uani 1 1 d . . . F4 F 0.0742(10) 0.2935(5) 0.2576(5) 0.074(3) Uani 1 1 d . . . F5 F 0.1419(9) 0.3855(5) 0.2434(5) 0.073(3) Uani 1 1 d . . . F6 F -0.0692(9) 0.3346(6) 0.2990(6) 0.080(4) Uani 1 1 d . . . P2 P -0.5722(3) 0.45201(17) 0.14339(18) 0.0479(11) Uani 1 1 d D . . F7 F -0.5855(14) 0.3894(4) 0.1109(7) 0.084(7) Uani 0.654(10) 1 d PD A 3 F8 F -0.5600(14) 0.5145(5) 0.1760(8) 0.104(8) Uani 0.654(10) 1 d PD A 3 F9 F -0.5088(14) 0.4200(8) 0.1976(5) 0.110(7) Uani 0.654(10) 1 d PD A 3 F10 F -0.6803(9) 0.4401(7) 0.1750(8) 0.087(6) Uani 0.654(10) 1 d PD A 3 F11 F -0.6389(15) 0.4826(8) 0.0897(6) 0.117(8) Uani 0.654(10) 1 d PD A 3 F12 F -0.4618(9) 0.4626(6) 0.1139(8) 0.087(6) Uani 0.654(10) 1 d PD A 3 F7' F -0.545(2) 0.3859(6) 0.1247(14) 0.084(7) Uani 0.346(10) 1 d PD A 4 F8' F -0.600(2) 0.5184(6) 0.1619(14) 0.104(8) Uani 0.346(10) 1 d PD A 4 F9' F -0.535(2) 0.4759(14) 0.0825(7) 0.110(7) Uani 0.346(10) 1 d PD A 4 F10' F -0.4523(9) 0.4607(12) 0.1716(11) 0.087(6) Uani 0.346(10) 1 d PD A 4 F11' F -0.610(2) 0.4288(14) 0.2041(7) 0.117(8) Uani 0.346(10) 1 d PD A 4 F12' F -0.6917(9) 0.4456(12) 0.1140(11) 0.087(6) Uani 0.346(10) 1 d PD A 4 C67 C -0.240(3) 0.4400(17) 0.2064(12) 0.135(14) Uani 1 1 d . . . H67A H -0.2116 0.4806 0.2134 0.202 Uiso 1 1 calc R . . H67B H -0.1968 0.4117 0.2315 0.202 Uiso 1 1 calc R . . H67C H -0.3165 0.4384 0.216 0.202 Uiso 1 1 calc R . . N68 N -0.2326(18) 0.4245(12) 0.1449(11) 0.092(6) Uani 1 1 d . . . O69 O -0.193(3) 0.4649(13) 0.1171(16) 0.207(17) Uani 1 1 d . . . O70 O -0.2625(17) 0.3769(10) 0.1254(9) 0.115(7) Uani 1 1 d . . . C72 C -0.116(5) 0.1386(19) 0.025(2) 0.128(14) Uani 0.654(10) 1 d PDU A 5 H72A H -0.1281 0.1271 0.0657 0.191 Uiso 0.654(10) 1 calc PR A 5 H72B H -0.178 0.1631 0.0087 0.191 Uiso 0.654(10) 1 calc PR A 5 H72C H -0.0485 0.1616 0.0241 0.191 Uiso 0.654(10) 1 calc PR A 5 N73 N -0.109(3) 0.0858(15) -0.0107(14) 0.149(14) Uani 0.654(10) 1 d PDU A 5 O74 O -0.089(5) 0.096(2) -0.0606(17) 0.21(2) Uani 0.654(10) 1 d PDU A 5 O75 O -0.109(5) 0.0368(16) 0.013(2) 0.28(3) Uani 0.654(10) 1 d PDU A 5 C72' C -0.099(9) 0.129(5) 0.033(4) 0.128(14) Uani 0.346(10) 1 d PDU A 6 H72D H -0.1733 0.1367 0.0447 0.191 Uiso 0.346(10) 1 calc PR A 6 H72E H -0.0583 0.1663 0.0322 0.191 Uiso 0.346(10) 1 calc PR A 6 H72F H -0.062 0.1009 0.0609 0.191 Uiso 0.346(10) 1 calc PR A 6 N73' N -0.106(4) 0.103(4) -0.025(3) 0.149(14) Uani 0.346(10) 1 d PDU A 6 O74' O -0.020(5) 0.088(5) -0.041(4) 0.21(2) Uani 0.346(10) 1 d PDU A 6 O75' O -0.194(5) 0.074(4) -0.040(4) 0.28(3) Uani 0.346(10) 1 d PDU A 6 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 O1 0.032(5) 0.053(6) 0.033(5) 0.013(4) -0.001(4) -0.003(4) O3 0.030(5) 0.035(5) 0.066(7) 0.006(5) -0.004(5) -0.004(4) O13 0.032(5) 0.037(5) 0.038(5) 0.010(4) -0.003(4) -0.002(4) O15 0.032(5) 0.054(6) 0.033(5) -0.012(5) 0.000(4) -0.005(4) O51 0.035(6) 0.058(7) 0.041(6) -0.011(5) 0.000(4) -0.005(5) O53 0.039(6) 0.069(8) 0.084(9) -0.036(7) -0.017(6) -0.006(6) O55 0.057(7) 0.042(6) 0.031(5) 0.004(4) 0.008(5) 0.010(5) O57 0.085(9) 0.028(5) 0.034(5) -0.001(4) -0.004(5) -0.011(5) O59 0.045(7) 0.034(6) 0.077(8) 0.004(5) -0.010(6) -0.011(5) O61 0.035(7) 0.039(7) 0.154(15) -0.022(8) -0.018(8) 0.007(5) O63 0.065(7) 0.036(6) 0.040(6) 0.005(4) 0.001(5) -0.018(5) N29 0.031(6) 0.031(6) 0.031(6) 0.005(5) -0.001(5) -0.004(5) N42 0.029(6) 0.044(7) 0.031(6) 0.008(5) 0.000(5) 0.005(5) C2 0.041(8) 0.037(8) 0.031(7) 0.003(6) -0.005(6) 0.002(6) C4 0.032(8) 0.035(7) 0.043(8) 0.003(6) -0.007(6) -0.005(6) C5 0.034(8) 0.039(8) 0.035(7) 0.001(6) -0.003(6) -0.005(6) C6 0.033(7) 0.038(7) 0.034(7) 0.001(6) -0.003(6) -0.006(6) C7 0.037(8) 0.032(7) 0.029(7) 0.003(5) -0.007(6) -0.003(6) C8 0.032(7) 0.028(7) 0.028(6) -0.003(5) -0.005(5) -0.004(5) C9 0.037(8) 0.032(7) 0.029(7) 0.003(5) -0.006(6) -0.003(6) C10 0.037(8) 0.030(7) 0.033(7) 0.000(5) -0.001(6) 0.002(6) C11 0.034(7) 0.040(8) 0.028(7) 0.002(6) -0.002(5) 0.004(6) C12 0.035(7) 0.032(7) 0.030(7) 0.005(5) -0.003(5) -0.003(6) C14 0.037(8) 0.032(7) 0.033(7) 0.005(6) -0.007(6) 0.001(6) C16 0.029(7) 0.040(8) 0.027(6) -0.001(6) 0.000(5) -0.004(6) C17 0.037(8) 0.031(7) 0.033(7) 0.004(6) -0.004(6) -0.007(6) C18 0.032(7) 0.032(7) 0.041(8) -0.001(6) -0.002(6) 0.002(6) C19 0.027(7) 0.036(7) 0.030(7) 0.003(5) 0.000(5) -0.001(5) C20 0.030(7) 0.032(7) 0.029(7) 0.005(5) -0.001(5) 0.002(5) C21 0.027(7) 0.034(7) 0.028(6) 0.005(5) -0.002(5) 0.002(5) C22 0.035(7) 0.034(7) 0.030(7) -0.002(6) -0.001(6) -0.006(6) C23 0.035(8) 0.034(7) 0.036(7) 0.007(6) -0.007(6) -0.008(6) C24 0.027(7) 0.042(8) 0.031(7) 0.008(6) 0.001(5) 0.001(6) C25 0.035(8) 0.043(8) 0.048(9) -0.007(7) -0.012(7) -0.004(6) C26 0.040(8) 0.043(8) 0.038(8) -0.004(6) -0.006(6) -0.004(6) C27 0.039(8) 0.029(7) 0.030(6) 0.000(5) -0.006(6) -0.004(6) C28 0.045(8) 0.033(7) 0.027(6) -0.001(6) -0.004(6) 0.001(6) C30 0.039(8) 0.032(7) 0.030(7) -0.001(5) -0.004(6) -0.003(6) C31 0.037(8) 0.031(7) 0.028(6) 0.001(5) -0.004(5) -0.004(6) C32 0.034(8) 0.040(8) 0.045(8) 0.008(7) 0.003(6) -0.004(6) C33 0.048(10) 0.055(11) 0.067(11) 0.002(9) 0.012(8) 0.009(8) C34 0.039(8) 0.035(7) 0.037(7) 0.007(6) 0.000(6) -0.005(6) C35 0.065(12) 0.071(12) 0.041(9) 0.020(9) -0.008(8) -0.016(9) C36 0.049(9) 0.034(7) 0.027(7) -0.001(6) -0.003(6) -0.007(6) C37 0.046(9) 0.029(7) 0.034(7) 0.000(6) -0.006(6) -0.007(6) C38 0.032(8) 0.034(8) 0.059(10) -0.008(7) -0.006(7) 0.003(6) C39 0.035(8) 0.031(7) 0.056(9) 0.001(7) -0.006(7) -0.004(6) C40 0.032(7) 0.038(7) 0.028(6) 0.005(6) 0.000(5) 0.004(6) C41 0.031(7) 0.037(7) 0.030(7) 0.000(6) -0.005(5) 0.004(6) C43 0.035(8) 0.038(8) 0.035(7) 0.004(6) -0.001(6) 0.005(6) C44 0.034(7) 0.031(7) 0.033(7) 0.007(6) -0.001(6) 0.003(6) C45 0.028(7) 0.053(9) 0.040(8) 0.000(7) -0.001(6) 0.006(6) C46 0.043(10) 0.078(13) 0.052(10) -0.006(9) -0.010(8) 0.001(9) C47 0.048(10) 0.067(11) 0.034(8) 0.011(7) -0.001(7) 0.006(8) C48 0.077(14) 0.068(13) 0.056(11) 0.016(10) 0.001(10) 0.013(10) C49 0.042(8) 0.031(7) 0.032(7) 0.001(6) -0.002(6) 0.005(6) C52 0.044(9) 0.056(10) 0.051(10) -0.017(8) 0.001(7) -0.005(8) C54 0.058(13) 0.089(16) 0.101(17) -0.054(14) -0.019(12) -0.005(11) C56 0.078(13) 0.048(10) 0.053(10) -0.009(8) 0.022(9) 0.009(9) C58 0.14(2) 0.037(9) 0.037(9) -0.007(7) -0.002(10) -0.021(11) C60 0.064(13) 0.032(9) 0.113(18) -0.008(10) -0.022(12) 0.000(8) C64 0.086(14) 0.038(9) 0.051(10) -0.002(7) -0.001(9) -0.019(9) C62 0.058(15) 0.026(10) 0.46(7) 0.00(2) -0.05(3) 0.004(10) C50 0.042(8) 0.040(8) 0.028(7) 0.000(6) -0.001(6) 0.004(6) O65 0.077(8) 0.048(6) 0.033(5) -0.004(5) 0.005(5) 0.012(6) C66 0.09(2) 0.08(2) 0.061(17) -0.023(15) 0.004(15) 0.041(17) C66' 0.09(2) 0.08(2) 0.061(17) -0.023(15) 0.004(15) 0.041(17) P1 0.054(3) 0.035(2) 0.038(2) 0.0018(16) -0.0053(17) -0.0013(17) F1 0.067(7) 0.063(6) 0.046(5) 0.002(5) -0.009(5) 0.007(5) F2 0.071(7) 0.039(5) 0.076(7) -0.004(5) -0.006(6) 0.007(5) F3 0.094(9) 0.079(8) 0.053(6) -0.003(6) -0.026(6) 0.009(7) F4 0.098(9) 0.046(6) 0.076(8) -0.011(5) -0.007(7) 0.015(6) F5 0.067(7) 0.080(8) 0.075(8) 0.020(6) 0.016(6) -0.006(6) F6 0.061(7) 0.078(8) 0.104(9) 0.010(7) 0.014(7) -0.019(6) P2 0.053(3) 0.045(2) 0.046(2) -0.0112(18) 0.0059(19) -0.0082(19) F7 0.135(19) 0.052(7) 0.070(12) -0.018(7) 0.031(12) -0.010(9) F8 0.108(18) 0.077(9) 0.136(16) -0.060(10) 0.077(14) -0.061(10) F9 0.125(18) 0.125(17) 0.074(12) 0.033(12) -0.022(12) -0.013(15) F10 0.082(12) 0.071(11) 0.113(15) -0.021(10) 0.050(11) -0.019(9) F11 0.14(2) 0.128(19) 0.084(13) 0.014(13) -0.028(13) 0.039(16) F12 0.067(11) 0.059(10) 0.140(17) -0.004(11) 0.048(11) -0.012(8) F7' 0.135(19) 0.052(7) 0.070(12) -0.018(7) 0.031(12) -0.010(9) F8' 0.108(18) 0.077(9) 0.136(16) -0.060(10) 0.077(14) -0.061(10) F9' 0.125(18) 0.125(17) 0.074(12) 0.033(12) -0.022(12) -0.013(15) F10' 0.082(12) 0.071(11) 0.113(15) -0.021(10) 0.050(11) -0.019(9) F11' 0.14(2) 0.128(19) 0.084(13) 0.014(13) -0.028(13) 0.039(16) F12' 0.067(11) 0.059(10) 0.140(17) -0.004(11) 0.048(11) -0.012(8) C67 0.12(2) 0.20(4) 0.080(19) -0.05(2) -0.018(17) 0.08(2) N68 0.084(15) 0.094(17) 0.101(17) 0.013(14) 0.020(12) 0.026(13) O69 0.23(3) 0.13(2) 0.28(4) 0.10(2) 0.15(3) 0.07(2) O70 0.125(17) 0.100(15) 0.117(16) -0.036(13) -0.018(12) 0.013(13) C72 0.08(3) 0.20(3) 0.10(3) 0.07(2) -0.010(18) -0.01(3) N73 0.16(3) 0.16(3) 0.12(3) 0.06(2) -0.04(3) -0.06(2) O74 0.30(5) 0.21(4) 0.13(3) 0.07(3) 0.06(4) 0.07(4) O75 0.38(5) 0.20(3) 0.25(5) 0.09(3) -0.10(5) -0.16(4) C72' 0.08(3) 0.20(3) 0.10(3) 0.07(2) -0.010(18) -0.01(3) N73' 0.16(3) 0.16(3) 0.12(3) 0.06(2) -0.04(3) -0.06(2) O74' 0.30(5) 0.21(4) 0.13(3) 0.07(3) 0.06(4) 0.07(4) O75' 0.38(5) 0.20(3) 0.25(5) 0.09(3) -0.10(5) -0.16(4) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 O1 C24 1.384(16) . ? O1 C2 1.413(16) . ? O3 C4 1.386(17) . ? O3 C2 1.418(17) . ? O13 C12 1.386(16) . ? O13 C14 1.409(16) . ? O15 C16 1.382(16) . ? O15 C14 1.413(16) . ? O51 C5 1.370(18) . ? O51 C52 1.433(18) . ? O53 C25 1.359(17) . ? O53 C54 1.43(2) . ? O55 C11 1.363(16) . ? O55 C56 1.421(19) . ? O57 C37 1.383(17) . ? O57 C58 1.432(19) . ? O59 C17 1.361(16) . ? O59 C60 1.45(2) . ? O61 C38 1.360(18) . ? O61 C62 1.41(3) . ? O63 C23 1.360(16) . ? O63 C64 1.44(2) . ? N29 C34 1.499(16) . ? N29 C30 1.509(17) . ? N29 C28 1.518(16) . ? N29 C32 1.519(18) . ? N42 C41 1.512(17) . ? N42 C43 1.519(18) . ? N42 C47 1.525(19) . ? N42 C45 1.527(18) . ? C4 C25 1.38(2) . ? C4 C5 1.397(19) . ? C5 C6 1.39(2) . ? C6 C7 1.39(2) . ? C7 C26 1.385(19) . ? C7 C8 1.552(19) . ? C8 C9 1.544(18) . ? C8 C31 1.549(17) . ? C8 C27 1.555(18) . ? C9 C10 1.386(19) . ? C9 C36 1.405(19) . ? C10 C11 1.400(19) . ? C11 C12 1.389(19) . ? C12 C37 1.396(19) . ? C16 C17 1.38(2) . ? C16 C38 1.39(2) . ? C17 C18 1.403(19) . ? C18 C19 1.386(19) . ? C19 C39 1.387(19) . ? C19 C20 1.541(18) . ? C20 C21 1.544(18) . ? C20 C44 1.546(18) . ? C20 C40 1.552(18) . ? C21 C49 1.388(19) . ? C21 C22 1.400(19) . ? C22 C23 1.386(19) . ? C23 C24 1.39(2) . ? C24 C50 1.39(2) . ? C25 C26 1.41(2) . ? C27 C28 1.52(2) . ? C30 C31 1.53(2) . ? C32 C33 1.50(2) . ? C34 C35 1.50(2) . ? C36 C37 1.38(2) . ? C38 C39 1.39(2) . ? C40 C41 1.519(18) . ? C43 C44 1.523(19) . ? C45 C46 1.51(2) . ? C47 C48 1.47(2) . ? C49 C50 1.376(19) . ? C50 O65 1.374(12) . ? O65 C66' 1.423(16) . ? O65 C66 1.431(15) . ? P1 F6 1.578(12) . ? P1 F3 1.581(11) . ? P1 F5 1.591(12) . ? P1 F1 1.591(10) . ? P1 F4 1.593(11) . ? P1 F2 1.599(10) . ? P2 F11 1.568(3) . ? P2 F12 1.569(3) . ? P2 F11' 1.569(3) . ? P2 F12' 1.571(3) . ? P2 F10' 1.571(3) . ? P2 F9' 1.572(3) . ? P2 F9 1.573(3) . ? P2 F10 1.573(3) . ? P2 F7' 1.580(3) . ? P2 F8 1.581(3) . ? P2 F7 1.581(3) . ? P2 F8' 1.582(3) . ? C67 N68 1.44(3) . ? N68 O70 1.20(3) . ? N68 O69 1.22(3) . ? C72 N73 1.431(3) . ? N73 O74 1.190(3) . ? N73 O75 1.221(3) . ? C72' N73' 1.430(3) . ? N73' O74' 1.190(3) . ? N73' O75' 1.28(5) . ? 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 C24 O1 C2 116.9(11) . . ? C4 O3 C2 118.3(11) . . ? C12 O13 C14 115.1(11) . . ? C16 O15 C14 117.7(11) . . ? C5 O51 C52 117.6(12) . . ? C25 O53 C54 117.0(14) . . ? C11 O55 C56 117.3(12) . . ? C37 O57 C58 117.1(12) . . ? C17 O59 C60 117.5(13) . . ? C38 O61 C62 116.4(15) . . ? C23 O63 C64 116.8(12) . . ? C34 N29 C30 112.2(11) . . ? C34 N29 C28 110.1(10) . . ? C30 N29 C28 107.3(10) . . ? C34 N29 C32 111.2(11) . . ? C30 N29 C32 107.2(10) . . ? C28 N29 C32 108.7(11) . . ? C41 N42 C43 108.0(10) . . ? C41 N42 C47 108.9(11) . . ? C43 N42 C47 113.5(12) . . ? C41 N42 C45 109.1(11) . . ? C43 N42 C45 106.4(11) . . ? C47 N42 C45 110.8(11) . . ? O1 C2 O3 108.3(11) . . ? C25 C4 O3 118.3(12) . . ? C25 C4 C5 119.2(13) . . ? O3 C4 C5 122.2(14) . . ? O51 C5 C6 124.5(12) . . ? O51 C5 C4 115.0(13) . . ? C6 C5 C4 120.5(14) . . ? C5 C6 C7 120.1(13) . . ? C26 C7 C6 119.7(14) . . ? C26 C7 C8 119.3(13) . . ? C6 C7 C8 121.0(12) . . ? C9 C8 C31 110.4(10) . . ? C9 C8 C7 108.5(11) . . ? C31 C8 C7 110.1(11) . . ? C9 C8 C27 112.9(11) . . ? C31 C8 C27 105.2(10) . . ? C7 C8 C27 109.7(11) . . ? C10 C9 C36 118.6(12) . . ? C10 C9 C8 122.8(12) . . ? C36 C9 C8 118.5(12) . . ? C9 C10 C11 121.0(13) . . ? O55 C11 C12 115.5(12) . . ? O55 C11 C10 124.6(13) . . ? C12 C11 C10 120.0(12) . . ? O13 C12 C11 120.3(12) . . ? O13 C12 C37 120.7(12) . . ? C11 C12 C37 118.9(12) . . ? O13 C14 O15 109.3(11) . . ? O15 C16 C17 122.2(13) . . ? O15 C16 C38 118.4(13) . . ? C17 C16 C38 119.1(12) . . ? O59 C17 C16 115.1(12) . . ? O59 C17 C18 124.1(13) . . ? C16 C17 C18 120.9(12) . . ? C19 C18 C17 119.7(13) . . ? C18 C19 C39 119.1(12) . . ? C18 C19 C20 122.3(12) . . ? C39 C19 C20 118.5(12) . . ? C19 C20 C21 106.1(10) . . ? C19 C20 C44 111.7(11) . . ? C21 C20 C44 112.2(11) . . ? C19 C20 C40 109.0(11) . . ? C21 C20 C40 113.1(11) . . ? C44 C20 C40 104.8(10) . . ? C49 C21 C22 118.3(12) . . ? C49 C21 C20 120.7(12) . . ? C22 C21 C20 120.8(12) . . ? C23 C22 C21 120.9(13) . . ? O63 C23 C22 123.8(13) . . ? O63 C23 C24 116.0(12) . . ? C22 C23 C24 120.2(13) . . ? O1 C24 C23 120.8(13) . . ? O1 C24 C50 120.4(12) . . ? C23 C24 C50 118.6(12) . . ? O53 C25 C4 115.9(14) . . ? O53 C25 C26 123.9(15) . . ? C4 C25 C26 120.3(13) . . ? C7 C26 C25 120.1(14) . . ? C28 C27 C8 114.7(11) . . ? C27 C28 N29 113.5(11) . . ? N29 C30 C31 112.9(11) . . ? C30 C31 C8 112.6(11) . . ? C33 C32 N29 115.9(13) . . ? N29 C34 C35 115.0(12) . . ? C37 C36 C9 120.2(13) . . ? C36 C37 O57 123.9(13) . . ? C36 C37 C12 121.2(13) . . ? O57 C37 C12 114.9(12) . . ? O61 C38 C39 124.8(14) . . ? O61 C38 C16 115.4(13) . . ? C39 C38 C16 119.8(13) . . ? C38 C39 C19 121.3(13) . . ? C41 C40 C20 113.0(11) . . ? N42 C41 C40 113.3(11) . . ? N42 C43 C44 114.1(11) . . ? C43 C44 C20 112.5(11) . . ? C46 C45 N42 115.9(13) . . ? C48 C47 N42 115.9(15) . . ? C50 C49 C21 120.7(13) . . ? O65 C50 C49 121.5(13) . . ? O65 C50 C24 117.4(12) . . ? C49 C50 C24 121.1(12) . . ? C50 O65 C66' 118(2) . . ? C50 O65 C66 114.6(15) . . ? C66' O65 C66 74(3) . . ? F6 P1 F3 90.9(7) . . ? F6 P1 F5 178.9(7) . . ? F3 P1 F5 90.2(7) . . ? F6 P1 F1 90.0(7) . . ? F3 P1 F1 178.6(7) . . ? F5 P1 F1 88.9(6) . . ? F6 P1 F4 90.2(7) . . ? F3 P1 F4 89.6(6) . . ? F5 P1 F4 89.8(7) . . ? F1 P1 F4 89.3(6) . . ? F6 P1 F2 89.9(7) . . ? F3 P1 F2 90.9(6) . . ? F5 P1 F2 90.0(6) . . ? F1 P1 F2 90.2(6) . . ? F4 P1 F2 179.4(7) . . ? F8 P2 F7 179.5(7) . . ? F9 P2 F7 89.3(7) . . ? F9 P2 F10 87.5(7) . . ? F10 P2 F8 89.5(6) . . ? F10 P2 F7 89.9(6) . . ? F11 P2 F7 89.8(7) . . ? F11 P2 F12 91.4(7) . . ? F11 P2 F9 178.1(8) . . ? F11 P2 F10 90.8(7) . . ? F11 P2 F8 90.1(7) . . ? F12 P2 F8 90.5(6) . . ? F12 P2 F9 90.3(7) . . ? F12 P2 F10 177.8(8) . . ? F12 P2 F7 90.0(6) . . ? F7' P2 F8' 179.7(10) . . ? F9' P2 F7' 90.1(8) . . ? F9' P2 F8' 89.6(7) . . ? F10' P2 F7' 90.7(7) . . ? F10' P2 F8' 89.2(7) . . ? F10' P2 F9' 89.4(7) . . ? F11' P2 F9' 179.3(9) . . ? F11' P2 F12' 90.6(7) . . ? F11' P2 F10' 91.0(7) . . ? F11' P2 F7' 90.5(8) . . ? F11' P2 F8' 89.8(7) . . ? F12' P2 F8' 89.3(7) . . ? F12' P2 F7' 90.8(7) . . ? F12' P2 F10' 177.9(8) . . ? F12' P2 F9' 89.1(7) . . ? O70 N68 O69 126(3) . . ? O70 N68 C67 122(3) . . ? O69 N68 C67 112(3) . . ? O74 N73 O75 127.1(5) . . ? O74 N73 C72 113.0(4) . . ? O75 N73 C72 119.2(4) . . ? O74' N73' O75' 122(4) . . ? O74' N73' C72' 113.1(4) . . ? O75' N73' C72' 115(3) . . ? 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 C24 O1 C2 O3 99.8(14) . . . . ? C4 O3 C2 O1 -125.8(13) . . . . ? C2 O3 C4 C25 128.9(14) . . . . ? C2 O3 C4 C5 -58.0(19) . . . . ? C52 O51 C5 C6 -8(2) . . . . ? C52 O51 C5 C4 173.5(13) . . . . ? C25 C4 C5 O51 174.7(13) . . . . ? O3 C4 C5 O51 2(2) . . . . ? C25 C4 C5 C6 -4(2) . . . . ? O3 C4 C5 C6 -176.9(13) . . . . ? O51 C5 C6 C7 -177.3(13) . . . . ? C4 C5 C6 C7 1(2) . . . . ? C5 C6 C7 C26 1(2) . . . . ? C5 C6 C7 C8 -176.9(12) . . . . ? C26 C7 C8 C9 -89.2(15) . . . . ? C6 C7 C8 C9 88.5(14) . . . . ? C26 C7 C8 C31 149.8(13) . . . . ? C6 C7 C8 C31 -32.4(17) . . . . ? C26 C7 C8 C27 34.5(17) . . . . ? C6 C7 C8 C27 -147.7(12) . . . . ? C31 C8 C9 C10 -130.9(14) . . . . ? C7 C8 C9 C10 108.4(15) . . . . ? C27 C8 C9 C10 -13.4(18) . . . . ? C31 C8 C9 C36 50.6(17) . . . . ? C7 C8 C9 C36 -70.2(15) . . . . ? C27 C8 C9 C36 168.0(12) . . . . ? C36 C9 C10 C11 0(2) . . . . ? C8 C9 C10 C11 -179.0(12) . . . . ? C56 O55 C11 C12 -176.9(14) . . . . ? C56 O55 C11 C10 2(2) . . . . ? C9 C10 C11 O55 -176.6(13) . . . . ? C9 C10 C11 C12 2(2) . . . . ? C14 O13 C12 C11 -111.2(14) . . . . ? C14 O13 C12 C37 73.0(16) . . . . ? O55 C11 C12 O13 -0.2(19) . . . . ? C10 C11 C12 O13 -179.3(12) . . . . ? O55 C11 C12 C37 175.6(13) . . . . ? C10 C11 C12 C37 -3(2) . . . . ? C12 O13 C14 O15 79.9(14) . . . . ? C16 O15 C14 O13 -132.6(12) . . . . ? C14 O15 C16 C17 -62.8(17) . . . . ? C14 O15 C16 C38 123.6(14) . . . . ? C60 O59 C17 C16 176.0(15) . . . . ? C60 O59 C17 C18 -5(2) . . . . ? O15 C16 C17 O59 6.9(19) . . . . ? C38 C16 C17 O59 -179.5(13) . . . . ? O15 C16 C17 C18 -172.6(12) . . . . ? C38 C16 C17 C18 1(2) . . . . ? O59 C17 C18 C19 -177.9(13) . . . . ? C16 C17 C18 C19 2(2) . . . . ? C17 C18 C19 C39 -4(2) . . . . ? C17 C18 C19 C20 178.8(12) . . . . ? C18 C19 C20 C21 110.9(14) . . . . ? C39 C19 C20 C21 -66.7(16) . . . . ? C18 C19 C20 C44 -11.6(18) . . . . ? C39 C19 C20 C44 170.8(13) . . . . ? C18 C19 C20 C40 -126.9(14) . . . . ? C39 C19 C20 C40 55.5(16) . . . . ? C19 C20 C21 C49 -78.9(15) . . . . ? C44 C20 C21 C49 43.3(17) . . . . ? C40 C20 C21 C49 161.6(12) . . . . ? C19 C20 C21 C22 96.3(14) . . . . ? C44 C20 C21 C22 -141.5(13) . . . . ? C40 C20 C21 C22 -23.2(17) . . . . ? C49 C21 C22 C23 3(2) . . . . ? C20 C21 C22 C23 -172.6(12) . . . . ? C64 O63 C23 C22 -14(2) . . . . ? C64 O63 C23 C24 167.0(14) . . . . ? C21 C22 C23 O63 -178.4(13) . . . . ? C21 C22 C23 C24 0(2) . . . . ? C2 O1 C24 C23 -113.7(15) . . . . ? C2 O1 C24 C50 70.8(17) . . . . ? O63 C23 C24 O1 0(2) . . . . ? C22 C23 C24 O1 -179.4(12) . . . . ? O63 C23 C24 C50 175.2(13) . . . . ? C22 C23 C24 C50 -4(2) . . . . ? C54 O53 C25 C4 170.8(18) . . . . ? C54 O53 C25 C26 -8(3) . . . . ? O3 C4 C25 O53 -1(2) . . . . ? C5 C4 C25 O53 -174.4(14) . . . . ? O3 C4 C25 C26 178.3(13) . . . . ? C5 C4 C25 C26 5(2) . . . . ? C6 C7 C26 C25 0(2) . . . . ? C8 C7 C26 C25 178.1(13) . . . . ? O53 C25 C26 C7 176.0(15) . . . . ? C4 C25 C26 C7 -3(2) . . . . ? C9 C8 C27 C28 -67.6(14) . . . . ? C31 C8 C27 C28 52.9(14) . . . . ? C7 C8 C27 C28 171.3(11) . . . . ? C8 C27 C28 N29 -56.0(15) . . . . ? C34 N29 C28 C27 -68.2(14) . . . . ? C30 N29 C28 C27 54.1(14) . . . . ? C32 N29 C28 C27 169.7(11) . . . . ? C34 N29 C30 C31 64.1(14) . . . . ? C28 N29 C30 C31 -56.9(14) . . . . ? C32 N29 C30 C31 -173.5(11) . . . . ? N29 C30 C31 C8 61.2(14) . . . . ? C9 C8 C31 C30 67.3(14) . . . . ? C7 C8 C31 C30 -172.8(11) . . . . ? C27 C8 C31 C30 -54.7(14) . . . . ? C34 N29 C32 C33 -54.6(17) . . . . ? C30 N29 C32 C33 -177.6(13) . . . . ? C28 N29 C32 C33 66.7(16) . . . . ? C30 N29 C34 C35 63.0(17) . . . . ? C28 N29 C34 C35 -177.7(14) . . . . ? C32 N29 C34 C35 -57.1(17) . . . . ? C10 C9 C36 C37 0(2) . . . . ? C8 C9 C36 C37 178.4(13) . . . . ? C9 C36 C37 O57 179.5(14) . . . . ? C9 C36 C37 C12 -1(2) . . . . ? C58 O57 C37 C36 -9(2) . . . . ? C58 O57 C37 C12 171.2(16) . . . . ? O13 C12 C37 C36 178.7(13) . . . . ? C11 C12 C37 C36 3(2) . . . . ? O13 C12 C37 O57 -2(2) . . . . ? C11 C12 C37 O57 -177.7(13) . . . . ? C62 O61 C38 C39 8(3) . . . . ? C62 O61 C38 C16 -172(3) . . . . ? O15 C16 C38 O61 -7(2) . . . . ? C17 C16 C38 O61 179.2(14) . . . . ? O15 C16 C38 C39 172.4(14) . . . . ? C17 C16 C38 C39 -1(2) . . . . ? O61 C38 C39 C19 178.6(16) . . . . ? C16 C38 C39 C19 -1(2) . . . . ? C18 C19 C39 C38 3(2) . . . . ? C20 C19 C39 C38 -179.0(14) . . . . ? C19 C20 C40 C41 177.1(11) . . . . ? C21 C20 C40 C41 -65.1(14) . . . . ? C44 C20 C40 C41 57.4(14) . . . . ? C43 N42 C41 C40 53.0(14) . . . . ? C47 N42 C41 C40 -70.7(14) . . . . ? C45 N42 C41 C40 168.3(11) . . . . ? C20 C40 C41 N42 -59.2(15) . . . . ? C41 N42 C43 C44 -52.8(15) . . . . ? C47 N42 C43 C44 68.1(15) . . . . ? C45 N42 C43 C44 -169.8(11) . . . . ? N42 C43 C44 C20 58.2(15) . . . . ? C19 C20 C44 C43 -174.4(11) . . . . ? C21 C20 C44 C43 66.6(15) . . . . ? C40 C20 C44 C43 -56.5(14) . . . . ? C41 N42 C45 C46 63.4(16) . . . . ? C43 N42 C45 C46 179.7(13) . . . . ? C47 N42 C45 C46 -56.5(18) . . . . ? C41 N42 C47 C48 -171.1(15) . . . . ? C43 N42 C47 C48 68.5(19) . . . . ? C45 N42 C47 C48 -51(2) . . . . ? C22 C21 C49 C50 -3(2) . . . . ? C20 C21 C49 C50 172.8(12) . . . . ? C21 C49 C50 O65 -178.6(13) . . . . ? C21 C49 C50 C24 -1(2) . . . . ? O1 C24 C50 O65 -2(2) . . . . ? C23 C24 C50 O65 -178.1(13) . . . . ? O1 C24 C50 C49 179.7(13) . . . . ? C23 C24 C50 C49 4(2) . . . . ? C49 C50 O65 C66' -16(4) . . . . ? C24 C50 O65 C66' 166(3) . . . . ? C49 C50 O65 C66 -101(2) . . . . ? C24 C50 O65 C66 82(2) . . . . ? #==END data_11 _audit_creation_date 1999-05-06T13:22:06-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; 1,1'Diacetyl-5,9,13,15,21,25,29,31-tetramethoxydispiro[1,3,17,19- tetraoxa[3,1,3,1]paracyclophane-10,4':26,4''-bispiperidine] ; _chemical_formula_sum 'C54.5 H70.5 Cl1.50 N2 O17' _chemical_formula_weight 1078.84 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 14.0149(12) _cell_length_b 12.7542(12) _cell_length_c 17.837(2) _cell_angle_alpha 90 _cell_angle_beta 108.711(8) _cell_angle_gamma 90 _cell_volume 3019.8(5) _cell_formula_units_Z 2 _cell_measurement_temperature 213(2) #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_diffrn 1.150 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1252 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 1.968 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details ; North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351 ; _exptl_absorpt_correction_T_min 0.8167 _exptl_absorpt_correction_T_max 0.9872 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 213(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Enraf Nonius MACH3' _diffrn_measurement_method 'non-profiled omega/2theta scans' _diffrn_standards_number 3 _diffrn_standards_interval_time 120 _diffrn_standards_decay_% 0 _diffrn_standards_decay_corr_max 1.039 _diffrn_standards_decay_corr_min 0.979 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l -1 -5 6 -4 1 8 -5 -1 -4 _diffrn_reflns_number 5311 _diffrn_reflns_av_R_equivalents 0.1111 _diffrn_reflns_av_sigmaI/netI 0.0708 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.51 _diffrn_reflns_theta_max 64.97 _diffrn_reflns_theta_full 64.97 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _reflns_number_total 5126 _reflns_number_gt 3024 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'CAD4 Express (Enraf Nonius, 1992)' _computing_cell_refinement 'CAD4 Express (Enraf Nonius, 1992)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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 _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_number_reflns 5126 _refine_ls_number_parameters 446 _refine_ls_number_restraints 118 _refine_ls_R_factor_all 0.1594 _refine_ls_R_factor_gt 0.0957 _refine_ls_wR_factor_ref 0.3056 _refine_ls_wR_factor_gt 0.2766 _refine_ls_goodness_of_fit_ref 1.1 _refine_ls_restrained_S_all 1.1 _refine_ls_shift/su_max 0.061 _refine_ls_shift/su_mean 0.002 _refine_diff_density_max 0.869 _refine_diff_density_min -0.588 _refine_diff_density_rms 0.103 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.018 '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' 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 N17 N -0.0191(3) -0.2139(3) 0.4015(2) 0.0339(10) Uani 1 1 d . . . O1 O 0.5021(2) -0.2712(2) 0.66195(19) 0.0328(8) Uani 1 1 d . . . O11 O 0.3248(2) 0.2669(2) 0.30624(19) 0.0301(8) Uani 1 1 d . . . O21 O -0.1648(3) -0.1298(3) 0.3903(2) 0.0467(10) Uani 1 1 d . . . O25 O 0.4294(3) -0.0854(3) 0.6821(2) 0.0379(8) Uani 1 1 d . . . O27 O 0.2511(3) 0.2865(2) 0.4264(2) 0.0452(10) Uani 1 1 d . . . O29 O 0.4162(3) -0.3853(2) 0.5284(2) 0.0424(9) Uani 1 1 d . . . O31 O 0.3245(3) 0.0818(3) 0.2360(2) 0.0400(9) Uani 1 1 d . . . C2 C 0.4235(3) -0.2305(3) 0.6005(3) 0.0274(10) Uani 1 1 d . . . C3 C 0.3839(4) -0.1340(3) 0.6118(3) 0.0309(11) Uani 1 1 d . . . C4 C 0.3001(3) -0.0938(3) 0.5521(3) 0.0305(11) Uani 1 1 d . . . H4 H 0.2726 -0.0292 0.5601 0.037 Uiso 1 1 calc R . . C5 C 0.2578(3) -0.1469(3) 0.4826(3) 0.0267(10) Uani 1 1 d . . . C6 C 0.1688(3) -0.0950(3) 0.4181(3) 0.0257(10) Uani 1 1 d . . . C7 C 0.2101(3) 0.0025(3) 0.3882(3) 0.0262(10) Uani 1 1 d . . . C8 C 0.2104(3) 0.1000(3) 0.4233(3) 0.0299(11) Uani 1 1 d . . . H8 H 0.1837 0.107 0.4651 0.036 Uiso 1 1 calc R . . C9 C 0.2502(3) 0.1876(3) 0.3966(3) 0.0290(10) Uani 1 1 d . . . C10 C 0.2913(3) 0.1786(3) 0.3359(3) 0.0278(10) Uani 1 1 d . . . C12 C 0.4137(3) 0.3127(3) 0.3566(3) 0.0319(11) Uani 1 1 d . . . H12A H 0.4204 0.2973 0.4119 0.038 Uiso 1 1 calc R . . H12B H 0.4109 0.3889 0.3496 0.038 Uiso 1 1 calc R . . C13 C 0.3775(3) -0.2868(3) 0.5317(3) 0.0310(11) Uani 1 1 d . . . C14 C 0.2962(3) -0.2438(3) 0.4717(3) 0.0289(10) Uani 1 1 d . . . H14 H 0.2677 -0.2805 0.424 0.035 Uiso 1 1 calc R . . C15 C 0.1163(3) -0.1674(3) 0.3469(3) 0.0247(10) Uani 1 1 d . . . H15A H 0.0729 -0.1241 0.304 0.03 Uiso 1 1 calc R . . H15B H 0.1681 -0.1985 0.3278 0.03 Uiso 1 1 calc R . . C16 C 0.0523(3) -0.2562(3) 0.3641(3) 0.0289(10) Uani 1 1 d . . . H16A H 0.0151 -0.2916 0.3146 0.035 Uiso 1 1 calc R . . H16B H 0.0963 -0.3078 0.3993 0.035 Uiso 1 1 calc R . . C18 C 0.0326(3) -0.1571(4) 0.4744(3) 0.0304(11) Uani 1 1 d . . . H18A H 0.0819 -0.2032 0.5111 0.037 Uiso 1 1 calc R . . H18B H -0.0163 -0.1347 0.5 0.037 Uiso 1 1 calc R . . C19 C 0.0854(3) -0.0626(3) 0.4556(3) 0.0282(10) Uani 1 1 d . . . H19A H 0.1166 -0.0226 0.5042 0.034 Uiso 1 1 calc R . . H19B H 0.0358 -0.0172 0.4185 0.034 Uiso 1 1 calc R . . C20 C -0.1163(4) -0.1874(4) 0.3611(3) 0.0371(12) Uani 1 1 d . . . C22 C -0.1626(4) -0.2329(6) 0.2798(4) 0.0608(18) Uani 1 1 d . . . H22A H -0.1132 -0.276 0.2665 0.091 Uiso 1 1 calc R . . H22B H -0.1841 -0.1766 0.2415 0.091 Uiso 1 1 calc R . . H22C H -0.2203 -0.2756 0.2788 0.091 Uiso 1 1 calc R . . C23 C 0.2500(3) -0.0061(3) 0.3260(3) 0.0291(10) Uani 1 1 d . . . H23 H 0.2507 -0.0716 0.302 0.035 Uiso 1 1 calc R . . C24 C 0.2888(3) 0.0821(3) 0.2991(3) 0.0289(10) Uani 1 1 d . . . C26 C 0.3819(5) 0.0062(5) 0.6985(4) 0.0592(17) Uani 1 1 d . . . H26A H 0.4211 0.0339 0.7498 0.089 Uiso 1 1 calc R . . H26B H 0.3147 -0.0112 0.6988 0.089 Uiso 1 1 calc R . . H26C H 0.3777 0.0584 0.658 0.089 Uiso 1 1 calc R . . C28 C 0.2159(7) 0.2986(5) 0.4923(5) 0.093(3) Uani 1 1 d . . . H28A H 0.2202 0.3718 0.5077 0.14 Uiso 1 1 calc R . . H28B H 0.2572 0.2568 0.5362 0.14 Uiso 1 1 calc R . . H28C H 0.1465 0.2753 0.478 0.14 Uiso 1 1 calc R . . C30 C 0.3632(4) -0.4529(4) 0.4660(4) 0.0506(15) Uani 1 1 d . . . H30A H 0.3988 -0.5191 0.471 0.076 Uiso 1 1 calc R . . H30B H 0.3585 -0.4208 0.4157 0.076 Uiso 1 1 calc R . . H30C H 0.2961 -0.4652 0.4686 0.076 Uiso 1 1 calc R . . C32 C 0.3441(4) -0.0162(4) 0.2077(3) 0.0406(13) Uani 1 1 d . . . H32A H 0.3688 -0.0059 0.1632 0.061 Uiso 1 1 calc R . . H32B H 0.2825 -0.0571 0.1907 0.061 Uiso 1 1 calc R . . H32C H 0.3945 -0.0533 0.2495 0.061 Uiso 1 1 calc R . . C34A C 0.4798(4) -0.3537(4) 0.2623(3) 0.072(6) Uani 0.451(4) 1 d PD A 1 H34A H 0.4144 -0.3822 0.2286 0.087 Uiso 0.451(4) 1 calc PR A 1 Cl1A Cl 0.5368(7) -0.2822(5) 0.2030(4) 0.116(4) Uani 0.451(4) 1 d PD A 1 Cl2A Cl 0.4596(6) -0.2698(5) 0.3348(4) 0.109(2) Uani 0.451(4) 1 d PD A 1 Cl3A Cl 0.5596(8) -0.4582(5) 0.3095(5) 0.120(2) Uani 0.451(4) 1 d PD A 1 C34B C 0.510(2) -0.372(2) 0.250(2) 0.072(6) Uani 0.049(4) 1 d PD A 2 H34B H 0.442 -0.3937 0.2171 0.087 Uiso 0.049(4) 1 calc PR A 2 Cl1B Cl 0.590(3) -0.367(3) 0.191(2) 0.116(4) Uani 0.049(4) 1 d PD A 2 Cl2B Cl 0.505(4) -0.247(3) 0.291(3) 0.109(2) Uani 0.049(4) 1 d PD A 2 Cl3B Cl 0.559(7) -0.464(4) 0.327(4) 0.120(2) Uani 0.049(4) 1 d PD A 2 C49 C -0.0503(17) 0.475(3) 0.4465(11) 0.160(9) Uani 0.5 1 d PDU B -3 H49A H -0.0173 0.4598 0.4075 0.24 Uiso 0.5 1 calc PR B -3 H49B H -0.0991 0.5303 0.4273 0.24 Uiso 0.5 1 calc PR B -3 H49C H -0.0844 0.4119 0.4554 0.24 Uiso 0.5 1 calc PR B -3 O50 O 0.0014(12) 0.5288(17) 0.5838(7) 0.172(8) Uani 0.5 1 d PDU B -3 C50 C 0.0291(14) 0.509(3) 0.5249(10) 0.173(9) Uani 0.5 1 d PDU B -3 O51 O 0.1227(10) 0.5524(15) 0.5244(8) 0.183(7) Uani 0.5 1 d PDU B -3 C52 C 0.1779(12) 0.5864(12) 0.6027(10) 0.142(7) Uani 0.5 1 d PDU B -3 H52A H 0.131 0.6041 0.6313 0.17 Uiso 0.5 1 calc PR B -3 H52B H 0.2167 0.6494 0.6 0.17 Uiso 0.5 1 calc PR B -3 C53 C 0.250(2) 0.4993(19) 0.6472(14) 0.208(14) Uani 0.5 1 d PDU B -3 H53A H 0.2868 0.5231 0.7002 0.311 Uiso 0.5 1 calc PR B -3 H53B H 0.2967 0.4825 0.6191 0.311 Uiso 0.5 1 calc PR B -3 H53C H 0.2112 0.4372 0.6503 0.311 Uiso 0.5 1 calc PR B -3 C40 C 0.5090(14) -0.1092(13) 0.4430(12) 0.159(8) Uani 0.5 1 d PDU C 4 H40A H 0.4737 -0.0588 0.403 0.238 Uiso 0.5 1 calc PR C 4 H40B H 0.5771 -0.0847 0.4692 0.238 Uiso 0.5 1 calc PR C 4 H40C H 0.474 -0.117 0.4816 0.238 Uiso 0.5 1 calc PR C 4 C41 C 0.5127(16) -0.2163(13) 0.4033(9) 0.174(9) Uani 0.5 1 d PDU C 4 O42 O 0.5555(17) -0.2925(13) 0.4457(11) 0.220(9) Uani 0.5 1 d PDU C 4 O43 O 0.4581(15) -0.2327(19) 0.3218(10) 0.206(10) Uani 0.5 1 d PDU C 4 C44 C 0.500(2) -0.3163(14) 0.2897(12) 0.205(12) Uani 0.5 1 d PDU C 4 H44A H 0.4506 -0.3727 0.2715 0.246 Uiso 0.5 1 calc PR C 4 H44B H 0.5594 -0.3448 0.3303 0.246 Uiso 0.5 1 calc PR C 4 C45 C 0.531(3) -0.273(2) 0.2196(19) 0.163(14) Uani 0.5 1 d PDU C 4 H45A H 0.5631 -0.3284 0.1991 0.244 Uiso 0.5 1 calc PR C 4 H45B H 0.5769 -0.2152 0.2375 0.244 Uiso 0.5 1 calc PR C 4 H45C H 0.471 -0.2495 0.1782 0.244 Uiso 0.5 1 calc PR C 4 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 N17 0.033(2) 0.033(2) 0.047(3) -0.0066(18) 0.028(2) -0.0025(17) O1 0.0308(17) 0.0370(18) 0.0382(19) 0.0028(15) 0.0217(15) 0.0103(14) O11 0.0283(16) 0.0262(16) 0.0406(18) 0.0056(14) 0.0177(14) -0.0039(13) O21 0.0333(19) 0.052(2) 0.062(2) -0.0088(19) 0.0257(18) 0.0058(17) O25 0.0380(19) 0.0356(19) 0.0398(19) -0.0083(15) 0.0120(16) 0.0051(15) O27 0.064(2) 0.0214(17) 0.072(3) -0.0052(16) 0.053(2) -0.0050(16) O29 0.0358(19) 0.0244(17) 0.063(2) -0.0087(17) 0.0099(17) 0.0072(15) O31 0.052(2) 0.0336(19) 0.049(2) -0.0046(15) 0.0373(18) -0.0078(16) C2 0.023(2) 0.024(2) 0.043(3) 0.004(2) 0.022(2) 0.0011(18) C3 0.037(3) 0.026(2) 0.039(3) -0.002(2) 0.025(2) -0.0009(19) C4 0.031(2) 0.023(2) 0.042(3) -0.001(2) 0.019(2) 0.0012(19) C5 0.027(2) 0.020(2) 0.041(3) 0.0016(19) 0.022(2) -0.0031(17) C6 0.024(2) 0.021(2) 0.038(3) -0.0044(19) 0.018(2) 0.0016(17) C7 0.025(2) 0.024(2) 0.032(2) 0.0026(19) 0.013(2) 0.0004(18) C8 0.036(3) 0.022(2) 0.041(3) 0.001(2) 0.025(2) 0.0010(19) C9 0.034(2) 0.019(2) 0.039(3) -0.0031(19) 0.020(2) -0.0027(18) C10 0.026(2) 0.024(2) 0.037(3) 0.0039(19) 0.016(2) -0.0019(18) C12 0.025(2) 0.022(2) 0.056(3) -0.002(2) 0.023(2) 0.0013(18) C13 0.030(2) 0.021(2) 0.047(3) -0.001(2) 0.020(2) 0.0032(18) C14 0.025(2) 0.024(2) 0.043(3) -0.002(2) 0.019(2) 0.0002(18) C15 0.026(2) 0.021(2) 0.034(2) -0.0008(18) 0.018(2) -0.0004(18) C16 0.029(2) 0.024(2) 0.042(3) -0.008(2) 0.023(2) -0.0023(19) C18 0.028(2) 0.029(2) 0.042(3) -0.002(2) 0.022(2) -0.0012(19) C19 0.029(2) 0.022(2) 0.042(3) -0.003(2) 0.024(2) 0.0018(18) C20 0.031(3) 0.036(3) 0.051(3) -0.002(2) 0.022(2) -0.001(2) C22 0.033(3) 0.085(5) 0.064(4) -0.021(4) 0.015(3) 0.001(3) C23 0.030(2) 0.021(2) 0.042(3) -0.0018(19) 0.020(2) -0.0007(18) C24 0.030(2) 0.029(2) 0.036(3) 0.0031(19) 0.022(2) 0.0019(19) C26 0.060(4) 0.047(3) 0.064(4) -0.021(3) 0.011(3) 0.013(3) C28 0.168(8) 0.038(4) 0.134(7) -0.037(4) 0.132(7) -0.031(4) C30 0.049(3) 0.027(3) 0.073(4) -0.011(3) 0.015(3) 0.009(2) C32 0.047(3) 0.039(3) 0.050(3) -0.004(2) 0.034(3) 0.003(2) C34A 0.047(10) 0.045(8) 0.093(11) 0.024(8) -0.023(8) -0.030(7) Cl1A 0.118(7) 0.142(8) 0.097(4) -0.002(4) 0.045(4) -0.082(6) Cl2A 0.134(6) 0.097(4) 0.101(4) 0.002(3) 0.047(4) -0.018(4) Cl3A 0.104(3) 0.047(2) 0.155(6) 0.006(3) -0.035(4) 0.008(2) C34B 0.047(10) 0.045(8) 0.093(11) 0.024(8) -0.023(8) -0.030(7) Cl1B 0.118(7) 0.142(8) 0.097(4) -0.002(4) 0.045(4) -0.082(6) Cl2B 0.134(6) 0.097(4) 0.101(4) 0.002(3) 0.047(4) -0.018(4) Cl3B 0.104(3) 0.047(2) 0.155(6) 0.006(3) -0.035(4) 0.008(2) C49 0.26(2) 0.17(3) 0.093(14) -0.006(15) 0.118(15) 0.08(2) O50 0.160(15) 0.28(2) 0.097(10) -0.015(12) 0.077(10) -0.041(15) C50 0.22(2) 0.18(2) 0.15(2) 0.00(2) 0.103(14) 0.054(19) O51 0.230(15) 0.193(16) 0.179(12) 0.070(13) 0.141(12) 0.067(13) C52 0.197(17) 0.130(17) 0.172(15) 0.042(13) 0.163(13) 0.035(12) C53 0.24(4) 0.13(2) 0.22(3) -0.038(19) 0.03(2) 0.028(19) C40 0.074(12) 0.178(15) 0.22(2) 0.117(14) 0.042(14) -0.025(13) C41 0.123(18) 0.188(16) 0.221(17) 0.112(13) 0.068(16) -0.030(15) O42 0.19(2) 0.202(17) 0.27(2) 0.107(16) 0.074(17) 0.038(16) O43 0.143(18) 0.30(3) 0.199(15) 0.082(15) 0.093(13) 0.001(16) C44 0.057(13) 0.23(3) 0.30(2) 0.006(18) 0.006(17) -0.059(17) C45 0.12(2) 0.091(18) 0.31(4) -0.13(2) 0.11(3) -0.044(16) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 N17 C20 1.364(6) . ? N17 C18 1.462(6) . ? N17 C16 1.470(5) . ? O1 C2 1.382(6) . ? O1 C12 1.427(5) 3_656 ? O11 C10 1.389(5) . ? O11 C12 1.407(6) . ? O21 C20 1.225(6) . ? O25 C3 1.360(6) . ? O25 C26 1.420(6) . ? O27 C9 1.367(5) . ? O27 C28 1.422(7) . ? O29 C13 1.376(5) . ? O29 C30 1.416(6) . ? O31 C24 1.371(5) . ? O31 C32 1.408(6) . ? C2 C13 1.389(7) . ? C2 C3 1.390(6) . ? C3 C4 1.405(7) . ? C4 C5 1.369(7) . ? C5 C14 1.386(6) . ? C5 C6 1.548(6) . ? C6 C7 1.536(6) . ? C6 C15 1.552(6) . ? C6 C19 1.577(5) . ? C7 C8 1.392(6) . ? C7 C23 1.398(6) . ? C8 C9 1.398(6) . ? C9 C10 1.385(6) . ? C10 C24 1.391(6) . ? C12 O1 1.427(5) 3_656 ? C13 C14 1.402(7) . ? C15 C16 1.536(6) . ? C18 C19 1.508(6) . ? C20 C22 1.503(8) . ? C23 C24 1.399(6) . ? C34A Cl2A 1.7697(11) . ? C34A Cl3A 1.7697(11) . ? C34A Cl1A 1.7697(10) . ? C34B Cl1B 1.7700(11) . ? C34B Cl3B 1.7700(11) . ? C34B Cl2B 1.7700(11) . ? C49 C50 1.545(5) . ? O50 C50 1.258(5) . ? C50 O51 1.428(5) . ? O51 C52 1.429(5) . ? C52 C53 1.538(5) . ? C40 C41 1.546(5) . ? C41 O42 1.259(5) . ? C41 O43 1.424(5) . ? O43 C44 1.425(5) . ? C44 C45 1.546(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C20 N17 C18 118.3(4) . . ? C20 N17 C16 124.1(4) . . ? C18 N17 C16 111.7(4) . . ? C2 O1 C12 117.6(3) . 3_656 ? C10 O11 C12 115.5(3) . . ? C3 O25 C26 116.9(4) . . ? C9 O27 C28 117.3(4) . . ? C13 O29 C30 118.4(4) . . ? C24 O31 C32 117.5(3) . . ? O1 C2 C13 122.1(4) . . ? O1 C2 C3 118.1(4) . . ? C13 C2 C3 119.5(4) . . ? O25 C3 C2 116.5(4) . . ? O25 C3 C4 124.2(4) . . ? C2 C3 C4 119.2(4) . . ? C5 C4 C3 121.3(4) . . ? C4 C5 C14 119.5(5) . . ? C4 C5 C6 118.3(4) . . ? C14 C5 C6 122.2(4) . . ? C7 C6 C5 107.5(3) . . ? C7 C6 C15 109.3(4) . . ? C5 C6 C15 114.3(3) . . ? C7 C6 C19 110.4(3) . . ? C5 C6 C19 109.1(4) . . ? C15 C6 C19 106.3(3) . . ? C8 C7 C23 118.8(4) . . ? C8 C7 C6 121.0(4) . . ? C23 C7 C6 120.2(4) . . ? C7 C8 C9 120.3(4) . . ? O27 C9 C10 115.2(4) . . ? O27 C9 C8 124.1(4) . . ? C10 C9 C8 120.8(4) . . ? C9 C10 O11 120.5(4) . . ? C9 C10 C24 119.2(4) . . ? O11 C10 C24 119.9(4) . . ? O11 C12 O1 109.1(4) . 3_656 ? O29 C13 C2 115.6(4) . . ? O29 C13 C14 124.0(4) . . ? C2 C13 C14 120.3(4) . . ? C5 C14 C13 119.9(5) . . ? C16 C15 C6 115.4(4) . . ? N17 C16 C15 110.2(3) . . ? N17 C18 C19 109.6(4) . . ? C18 C19 C6 111.6(3) . . ? O21 C20 N17 121.3(5) . . ? O21 C20 C22 121.1(5) . . ? N17 C20 C22 117.6(4) . . ? C7 C23 C24 120.6(4) . . ? O31 C24 C10 115.4(4) . . ? O31 C24 C23 124.4(4) . . ? C10 C24 C23 120.2(4) . . ? Cl2A C34A Cl3A 109.45(9) . . ? Cl2A C34A Cl1A 109.46(9) . . ? Cl3A C34A Cl1A 109.52(9) . . ? Cl1B C34B Cl3B 109.45(9) . . ? Cl1B C34B Cl2B 109.45(9) . . ? Cl3B C34B Cl2B 109.45(9) . . ? O50 C50 O51 117.1(9) . . ? O50 C50 C49 119.2(6) . . ? O51 C50 C49 120.0(6) . . ? C50 O51 C52 108.8(7) . . ? O51 C52 C53 110.2(8) . . ? O42 C41 O43 119.7(8) . . ? O42 C41 C40 119.1(7) . . ? O43 C41 C40 120.7(7) . . ? C41 O43 C44 111.3(8) . . ? O43 C44 C45 108.5(8) . . ? #==END data_15 #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; 1',1''-Diethyl-6,10,14,16,23,27,30,32-tetramethoxydispiro[1,4,18,21- tetraoxa[4,1,4,1]paracyclophane-11,4':28,4''-bispiperdine] ; _chemical_formula_sum 'C50 H66 N2 O12' _chemical_formula_weight 887.08 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.466(2) _cell_length_b 11.9827(18) _cell_length_c 16.456(2) _cell_angle_alpha 90 _cell_angle_beta 105.918(12) _cell_angle_gamma 90 _cell_volume 2363.9(6) _cell_formula_units_Z 2 _cell_measurement_temperature 213(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 22 _cell_measurement_theta_max 42 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.5 _exptl_crystal_size_min 0.25 _exptl_crystal_density_diffrn 1.246 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 952 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.722 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details ; North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351 ; _exptl_absorpt_correction_T_min 0.45 _exptl_absorpt_correction_T_max 0.9949 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 213(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_monochromator graphite _diffrn_detector 'scintillation LiI' _diffrn_orient_matrix_type ; x-axis points to radiation source the matrix is specified in reciprocal space ; _diffrn_orient_matrix_ub_11 -0.032 _diffrn_orient_matrix_ub_12 -0.06298 _diffrn_orient_matrix_ub_13 0.25679E-1 _diffrn_orient_matrix_ub_21 0.67597E-1 _diffrn_orient_matrix_ub_22 0.178E-3 _diffrn_orient_matrix_ub_23 0.49726E-1 _diffrn_orient_matrix_ub_31 -0.37077E-1 _diffrn_orient_matrix_ub_32 0.54807E-1 _diffrn_orient_matrix_ub_33 0.29324E-1 _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_measurement_device_type 'Enraf Nonius MACH 3' _diffrn_measurement_method 'non-profiled omega/2theta scans' _diffrn_standards_number 3 _diffrn_standards_interval_time 120 _diffrn_standards_decay_% 4 _diffrn_standards_decay_corr_max 1.111 _diffrn_standards_decay_corr_min 1 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l -1 2 8 1 -6 1 10 3 0 _diffrn_reflns_number 4977 _diffrn_reflns_av_R_equivalents 0.0668 _diffrn_reflns_av_sigmaI/netI 0.0184 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.97 _diffrn_reflns_theta_max 74.26 _diffrn_reflns_theta_full 74.26 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _reflns_number_total 4810 _reflns_number_gt 4128 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'CAD4 Express (Enraf Nonius, 1994)' _computing_cell_refinement 'CAD4 Express (Enraf Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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 _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_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.0021(4) _refine_ls_number_reflns 4810 _refine_ls_number_parameters 290 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0728 _refine_ls_R_factor_gt 0.0647 _refine_ls_wR_factor_ref 0.1961 _refine_ls_wR_factor_gt 0.1879 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.074 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.464 _refine_diff_density_min -0.338 _refine_diff_density_rms 0.074 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.018 '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' 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 O1 O 0.38828(12) -0.25313(15) 0.04118(9) 0.0473(4) Uani 1 1 d . . . C2 C 0.28149(17) -0.28845(19) 0.04775(12) 0.0394(5) Uani 1 1 d . . . H2A H 0.2497 -0.3438 0.0039 0.047 Uiso 1 1 calc R . . H2B H 0.2306 -0.2245 0.0398 0.047 Uiso 1 1 calc R . . C3 C 0.29522(17) -0.33878(16) 0.13381(12) 0.0355(4) Uani 1 1 d . . . H3A H 0.241 -0.3995 0.1286 0.043 Uiso 1 1 calc R . . H3B H 0.3699 -0.3717 0.153 0.043 Uiso 1 1 calc R . . O4 O 0.28116(11) -0.26291(11) 0.19706(8) 0.0335(3) Uani 1 1 d . . . C5 C 0.35205(15) -0.17251(15) 0.21459(11) 0.0297(4) Uani 1 1 d . . . C6 C 0.46420(15) -0.18374(15) 0.25851(11) 0.0308(4) Uani 1 1 d . . . C7 C 0.53112(15) -0.08976(16) 0.28179(12) 0.0317(4) Uani 1 1 d . . . H7 H 0.6071 -0.0984 0.3103 0.038 Uiso 1 1 calc R . . C8 C 0.48684(15) 0.01725(15) 0.26336(11) 0.0298(4) Uani 1 1 d . . . C9 C 0.56087(15) 0.12249(15) 0.28037(11) 0.0303(4) Uani 1 1 d . . . C10 C 0.42380(15) -0.16082(16) -0.19518(12) 0.0321(4) Uani 1 1 d . . . C11 C 0.43195(16) -0.27193(17) -0.17063(13) 0.0360(4) Uani 1 1 d . . . H11 H 0.4493 -0.3264 -0.2062 0.043 Uiso 1 1 calc R . . C12 C 0.41460(17) -0.30357(18) -0.09348(13) 0.0394(5) Uani 1 1 d . . . C13 C 0.39079(17) -0.22320(19) -0.03942(12) 0.0391(5) Uani 1 1 d . . . C27 C 0.30743(15) -0.06597(16) 0.19592(12) 0.0323(4) Uani 1 1 d . . . C28 C 0.37414(15) 0.02824(16) 0.22020(12) 0.0327(4) Uani 1 1 d . . . H28 H 0.343 0.0997 0.2074 0.039 Uiso 1 1 calc R . . C29 C 0.39525(17) -0.08145(17) -0.14255(13) 0.0385(5) Uani 1 1 d . . . H29 H 0.3867 -0.0063 -0.1594 0.046 Uiso 1 1 calc R . . C30 C 0.37947(18) -0.11288(19) -0.06537(13) 0.0414(5) Uani 1 1 d . . . C35 C 0.50814(16) 0.21412(16) 0.32394(12) 0.0329(4) Uani 1 1 d . . . H35A H 0.547 0.2849 0.3227 0.04 Uiso 1 1 calc R . . H35B H 0.4299 0.2243 0.2922 0.04 Uiso 1 1 calc R . . C36 C 0.51416(17) 0.18527(17) 0.41469(13) 0.0362(4) Uani 1 1 d . . . H36A H 0.4775 0.2439 0.4389 0.043 Uiso 1 1 calc R . . H36B H 0.4745 0.115 0.4163 0.043 Uiso 1 1 calc R . . N37 N 0.62978(14) 0.17422(14) 0.46488(10) 0.0356(4) Uani 1 1 d . . . C38 C 0.68112(17) 0.08094(17) 0.43180(13) 0.0364(4) Uani 1 1 d . . . H38A H 0.6409 0.0118 0.436 0.044 Uiso 1 1 calc R . . H38B H 0.7586 0.072 0.4657 0.044 Uiso 1 1 calc R . . C39 C 0.67823(15) 0.10181(17) 0.34002(12) 0.0333(4) Uani 1 1 d . . . H39A H 0.7111 0.0372 0.3192 0.04 Uiso 1 1 calc R . . H39B H 0.7251 0.1667 0.3376 0.04 Uiso 1 1 calc R . . C40 C 0.6384(2) 0.1592(2) 0.55465(13) 0.0438(5) Uani 1 1 d . . . H40A H 0.6061 0.0869 0.5627 0.053 Uiso 1 1 calc R . . H40B H 0.5948 0.2175 0.5727 0.053 Uiso 1 1 calc R . . C41 C 0.7573(2) 0.1641(2) 0.60962(14) 0.0494(5) Uani 1 1 d . . . H41A H 0.7582 0.1537 0.6683 0.074 Uiso 1 1 calc R . . H41B H 0.7893 0.2361 0.603 0.074 Uiso 1 1 calc R . . H41C H 0.8006 0.1055 0.5929 0.074 Uiso 1 1 calc R . . O42 O 0.41966(16) -0.41161(14) -0.06568(11) 0.0546(5) Uani 1 1 d . . . C42 C 0.4532(2) -0.4937(2) -0.11592(18) 0.0525(6) Uani 1 1 d . . . H42A H 0.4535 -0.5665 -0.09 0.079 Uiso 1 1 calc R . . H42B H 0.5275 -0.4765 -0.1201 0.079 Uiso 1 1 calc R . . H42C H 0.4014 -0.4943 -0.172 0.079 Uiso 1 1 calc R . . O43 O 0.35347(17) -0.03966(16) -0.00955(11) 0.0615(5) Uani 1 1 d . . . C43 C 0.3391(3) 0.0737(2) -0.0340(2) 0.0711(8) Uani 1 1 d . . . H43A H 0.3212 0.1167 0.0105 0.107 Uiso 1 1 calc R . . H43B H 0.2788 0.0802 -0.0855 0.107 Uiso 1 1 calc R . . H43C H 0.4075 0.1019 -0.0437 0.107 Uiso 1 1 calc R . . O49 O 0.50033(12) -0.29145(11) 0.27582(10) 0.0411(4) Uani 1 1 d . . . C49 C 0.6120(2) -0.3089(2) 0.3218(2) 0.0592(7) Uani 1 1 d . . . H49A H 0.6261 -0.3883 0.3295 0.089 Uiso 1 1 calc R . . H49B H 0.6259 -0.2731 0.3766 0.089 Uiso 1 1 calc R . . H49C H 0.661 -0.2773 0.2911 0.089 Uiso 1 1 calc R . . C48 C 0.1466(2) 0.0405(2) 0.12753(19) 0.0578(7) Uani 1 1 d . . . H48A H 0.0683 0.0298 0.0985 0.087 Uiso 1 1 calc R . . H48B H 0.1837 0.0757 0.0896 0.087 Uiso 1 1 calc R . . H48C H 0.1534 0.0877 0.1766 0.087 Uiso 1 1 calc R . . O48 O 0.19661(11) -0.06405(13) 0.15369(11) 0.0452(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0427(8) 0.0724(11) 0.0302(7) 0.0027(7) 0.0159(6) -0.0142(7) C2 0.0383(10) 0.0506(12) 0.0327(10) -0.0049(8) 0.0153(8) -0.0090(9) C3 0.0430(10) 0.0326(9) 0.0364(10) -0.0045(7) 0.0200(8) -0.0041(8) O4 0.0360(7) 0.0350(7) 0.0362(7) -0.0056(5) 0.0213(5) -0.0066(5) C5 0.0323(9) 0.0329(9) 0.0289(8) -0.0015(7) 0.0168(7) -0.0032(7) C6 0.0354(9) 0.0304(9) 0.0306(8) 0.0019(7) 0.0160(7) 0.0021(7) C7 0.0294(9) 0.0353(9) 0.0331(9) -0.0004(7) 0.0130(7) 0.0000(7) C8 0.0320(9) 0.0328(9) 0.0296(8) -0.0016(7) 0.0170(7) -0.0017(7) C9 0.0328(9) 0.0296(9) 0.0339(9) -0.0020(7) 0.0184(7) -0.0009(7) C10 0.0318(9) 0.0350(9) 0.0340(9) -0.0032(7) 0.0166(7) -0.0026(7) C11 0.0386(10) 0.0364(10) 0.0384(10) 0.0008(8) 0.0196(8) 0.0034(8) C12 0.0390(10) 0.0427(11) 0.0404(10) 0.0052(8) 0.0176(8) 0.0018(8) C13 0.0383(10) 0.0523(12) 0.0310(10) -0.0005(8) 0.0169(8) -0.0067(9) C27 0.0299(9) 0.0376(10) 0.0330(9) -0.0026(7) 0.0148(7) 0.0006(7) C28 0.0356(9) 0.0307(9) 0.0357(9) -0.0011(7) 0.0164(8) 0.0033(7) C29 0.0469(11) 0.0357(10) 0.0404(11) -0.0046(8) 0.0249(9) -0.0031(8) C30 0.0461(11) 0.0477(12) 0.0378(10) -0.0118(9) 0.0242(9) -0.0090(9) C35 0.0348(9) 0.0312(9) 0.0380(10) -0.0031(7) 0.0188(8) 0.0005(7) C36 0.0394(10) 0.0361(10) 0.0406(10) -0.0046(8) 0.0235(8) -0.0003(8) N37 0.0406(9) 0.0395(9) 0.0320(8) -0.0033(6) 0.0190(7) -0.0028(7) C38 0.0368(9) 0.0394(10) 0.0357(10) -0.0036(8) 0.0143(8) 0.0015(8) C39 0.0309(9) 0.0377(10) 0.0362(10) -0.0046(7) 0.0174(7) -0.0012(7) C40 0.0560(13) 0.0473(12) 0.0362(10) -0.0019(8) 0.0262(9) -0.0085(10) C41 0.0606(14) 0.0582(14) 0.0330(10) -0.0020(9) 0.0191(10) -0.0046(11) O42 0.0730(11) 0.0475(9) 0.0531(9) 0.0152(7) 0.0337(8) 0.0110(8) C42 0.0521(13) 0.0436(12) 0.0691(15) 0.0107(11) 0.0292(12) 0.0071(10) O43 0.0932(14) 0.0549(10) 0.0541(10) -0.0183(8) 0.0500(10) -0.0118(9) C43 0.098(2) 0.0546(16) 0.0777(19) -0.0240(14) 0.0530(18) -0.0019(15) O49 0.0395(7) 0.0304(7) 0.0518(9) 0.0047(6) 0.0098(6) 0.0019(6) C49 0.0463(13) 0.0412(12) 0.0804(18) 0.0066(12) 0.0011(12) 0.0078(10) C48 0.0400(11) 0.0507(14) 0.0744(17) -0.0108(12) 0.0014(11) 0.0123(10) O48 0.0309(7) 0.0397(8) 0.0615(10) -0.0045(7) 0.0067(6) 0.0023(6) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 O1 C13 1.383(2) . ? O1 C2 1.429(2) . ? C2 C3 1.505(3) . ? C3 O4 1.429(2) . ? O4 C5 1.378(2) . ? C5 C27 1.393(3) . ? C5 C6 1.393(3) . ? C6 O49 1.371(2) . ? C6 C7 1.391(3) . ? C7 C8 1.396(3) . ? C8 C28 1.396(3) . ? C8 C9 1.542(3) . ? C9 C10 1.536(2) 3_655 ? C9 C39 1.542(3) . ? C9 C35 1.553(2) . ? C10 C11 1.387(3) . ? C10 C29 1.397(3) . ? C10 C9 1.536(2) 3_655 ? C11 C12 1.398(3) . ? C12 O42 1.369(3) . ? C12 C13 1.397(3) . ? C13 C30 1.384(3) . ? C27 O48 1.366(2) . ? C27 C28 1.394(3) . ? C29 C30 1.390(3) . ? C30 O43 1.372(2) . ? C35 C36 1.514(3) . ? C36 N37 1.457(3) . ? N37 C40 1.462(2) . ? N37 C38 1.465(2) . ? C38 C39 1.522(3) . ? C40 C41 1.510(3) . ? O42 C42 1.420(3) . ? O43 C43 1.414(4) . ? O49 C49 1.406(3) . ? C48 O48 1.413(3) . ? 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 C13 O1 C2 114.59(16) . . ? O1 C2 C3 108.79(16) . . ? O4 C3 C2 115.18(17) . . ? C5 O4 C3 116.94(13) . . ? O4 C5 C27 118.69(16) . . ? O4 C5 C6 121.84(17) . . ? C27 C5 C6 119.09(16) . . ? O49 C6 C7 124.53(17) . . ? O49 C6 C5 115.12(16) . . ? C7 C6 C5 120.35(17) . . ? C6 C7 C8 120.81(17) . . ? C28 C8 C7 118.69(17) . . ? C28 C8 C9 118.94(16) . . ? C7 C8 C9 122.03(16) . . ? C10 C9 C39 107.17(14) 3_655 . ? C10 C9 C8 107.27(14) 3_655 . ? C39 C9 C8 113.59(15) . . ? C10 C9 C35 112.61(15) 3_655 . ? C39 C9 C35 105.53(15) . . ? C8 C9 C35 110.73(14) . . ? C11 C10 C29 118.93(18) . . ? C11 C10 C9 122.37(16) . 3_655 ? C29 C10 C9 118.62(17) . 3_655 ? C10 C11 C12 120.52(18) . . ? O42 C12 C13 115.96(19) . . ? O42 C12 C11 123.76(19) . . ? C13 C12 C11 120.3(2) . . ? O1 C13 C30 121.09(19) . . ? O1 C13 C12 119.8(2) . . ? C30 C13 C12 118.91(18) . . ? O48 C27 C5 114.51(16) . . ? O48 C27 C28 124.95(17) . . ? C5 C27 C28 120.55(17) . . ? C27 C28 C8 120.50(17) . . ? C30 C29 C10 120.42(19) . . ? O43 C30 C13 115.28(19) . . ? O43 C30 C29 123.9(2) . . ? C13 C30 C29 120.85(19) . . ? C36 C35 C9 112.40(16) . . ? N37 C36 C35 110.70(15) . . ? C36 N37 C40 111.79(15) . . ? C36 N37 C38 108.88(15) . . ? C40 N37 C38 111.27(17) . . ? N37 C38 C39 110.46(16) . . ? C38 C39 C9 114.73(15) . . ? N37 C40 C41 112.89(17) . . ? C12 O42 C42 117.06(17) . . ? C30 O43 C43 117.29(19) . . ? C6 O49 C49 118.17(16) . . ? C27 O48 C48 118.05(17) . . ? #==END