# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2009 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Scott Dalgarno' _publ_contact_author_email S.J.DALGARNO@HW.AC.UK _publ_section_title ; Modulation of nanotube packing through the controlled self-assembly of tris-p-carboxylatocalix[4]arenes ; loop_ _publ_author_name 'Scott Dalgarno' 'Stuart Kennedy' # Attachment '10Pynew.cif' data_10Py _database_code_depnum_ccdc_archive 'CCDC 731798' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'DiOPr Cal4 Tri Acid Py' _chemical_melting_point ? _chemical_formula_moiety '2(C37 H35 O10), 2(C5 H5 N), O' _chemical_formula_sum 'C42 H40 N O10.50' _chemical_formula_weight 726.75 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting trigonal _symmetry_space_group_name_H-M R-3 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' _cell_length_a 46.279(2) _cell_length_b 46.279(2) _cell_length_c 12.4670(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 23124(2) _cell_formula_units_Z 18 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used . _cell_measurement_theta_min . _cell_measurement_theta_max . _exptl_crystal_description Needle _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 0.939 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 6894 _exptl_absorpt_coefficient_mu 0.068 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6219 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _exptl_special_details ; Data were corrected for decay and absorption using the program SADABS based on the method of R.H. Blessing (Acta Cryst. A51, 33-38, 1995). ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius APEX II CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 54718 _diffrn_reflns_av_R_equivalents 0.1266 _diffrn_reflns_av_sigmaI/netI 0.1689 _diffrn_reflns_limit_h_min -55 _diffrn_reflns_limit_h_max 59 _diffrn_reflns_limit_k_min -60 _diffrn_reflns_limit_k_max 32 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.02 _diffrn_reflns_theta_max 27.48 _reflns_number_total 11661 _reflns_number_gt 3763 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XSeed (Barbour, 2001)' _computing_publication_material 'local program' _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. The structure possesses large channels that are not involved in linking the nanotubes together. The result of this is that the pyridine molecules of crystallisation that occupy this space are very badly disordered. It was not possible to model the disorder in these molecules and as this was the case, the routine SQUEEZE was applid to the data to remove the diffuse electron density. This dramatically improved the agreement indices. Some restraints were applied to the data due to disorder of one carboxylato group over two positions on the calixarene framework. In addition to this, some atoms were refined isotropically due to disorder. The crystals were very weakly diffracting and required a rotating anode source. Even with long exposure times, diffraction was still relatively weak at high angle. ; _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^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 11661 _refine_ls_number_parameters 496 _refine_ls_number_restraints 24 _refine_ls_R_factor_all 0.2861 _refine_ls_R_factor_gt 0.1406 _refine_ls_wR_factor_ref 0.4184 _refine_ls_wR_factor_gt 0.3545 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.032 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.000 0.000 0.000 19 3 ' ' 2 0.000 0.000 0.244 12 1 ' ' 3 0.000 0.000 0.500 11 2 ' ' 4 0.000 0.000 0.756 11 2 ' ' 5 0.004 0.302 0.507 6631 912 ' ' 6 0.333 0.667 0.667 20 3 ' ' 7 0.333 0.667 0.167 10 1 ' ' 8 0.333 0.667 0.422 11 2 ' ' 9 0.333 0.667 0.911 11 1 ' ' 10 0.667 0.333 0.333 20 3 ' ' 11 0.667 0.333 0.089 11 2 ' ' 12 0.667 0.333 0.578 11 1 ' ' 13 0.667 0.333 0.833 10 1 ' ' #_platon_squeeze_details 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 0.81181(12) 0.11196(13) 0.6704(4) 0.0548(14) Uani 0.65 1 d P . . H1S H 0.7998 0.1204 0.6562 0.066 Uiso 0.65 1 calc PR . . C1 C 0.87062(14) 0.06912(12) 0.7175(4) 0.0599(14) Uani 1 1 d . . . O2 O 0.83205(15) 0.12892(16) 0.5057(4) 0.0735(18) Uani 0.65 1 d P . . C2 C 0.85072(13) 0.08356(13) 0.7007(5) 0.0645(15) Uani 1 1 d . . . H2 H 0.8353 0.0818 0.7542 0.077 Uiso 1 1 calc R . . O3 O 0.97691(16) 0.19965(16) 0.2201(5) 0.127(2) Uani 1 1 d . . . C3 C 0.85348(13) 0.10027(13) 0.6068(4) 0.0602(14) Uani 1 1 d . . . O4 O 1.01559(15) 0.23941(15) 0.3204(4) 0.1224(18) Uani 1 1 d . . . H4S H 1.0173 0.2509 0.2660 0.147 Uiso 1 1 calc R . . C4 C 0.87689(13) 0.10409(13) 0.5316(5) 0.0636(14) Uani 1 1 d . . . H4 H 0.8790 0.1162 0.4679 0.076 Uiso 1 1 calc R . . O5 O 1.0021(2) 0.2651(2) 0.8066(7) 0.051(2) Uiso 0.35 1 d P . . C5 C 0.89688(13) 0.09104(13) 0.5459(5) 0.0592(14) Uani 1 1 d . . . O6 O 0.9919(2) 0.2534(2) 0.9663(8) 0.060(2) Uiso 0.35 1 d P . . H6S H 0.9896 0.2702 0.9607 0.072 Uiso 0.35 1 calc PR . . C6 C 0.89244(13) 0.07233(13) 0.6365(5) 0.0615(14) Uani 1 1 d . . . O7 O 0.87769(15) 0.11994(18) 1.2527(6) 0.145(2) Uani 1 1 d . . . C7 C 0.92353(13) 0.09624(13) 0.4634(4) 0.0667(15) Uani 1 1 d . . . H7A H 0.9308 0.0798 0.4763 0.080 Uiso 1 1 calc R . . H7B H 0.9137 0.0923 0.3906 0.080 Uiso 1 1 calc R . . O8 O 0.83350(14) 0.09475(14) 1.1463(5) 0.1231(18) Uani 1 1 d . . . H8S H 0.8242 0.0950 1.2039 0.148 Uiso 1 1 calc R . . C8 C 0.95367(14) 0.13128(15) 0.4688(5) 0.0656(15) Uani 1 1 d . . . O9 O 0.91284(9) 0.05808(9) 0.6566(3) 0.0757(12) Uani 1 1 d . . . C9 C 0.95946(15) 0.15491(17) 0.3922(4) 0.0660(15) Uani 1 1 d . . . H9 H 0.9438 0.1493 0.3354 0.079 Uiso 1 1 calc R . . O10 O 0.97300(9) 0.11680(10) 0.6245(3) 0.0755(11) Uani 1 1 d . . . H10 H 0.9881 0.1250 0.6713 0.091 Uiso 1 1 calc R . . C10 C 0.98661(17) 0.18596(16) 0.3944(6) 0.0739(16) Uani 1 1 d . . . O11 O 1.00729(8) 0.13242(9) 0.8159(3) 0.0759(12) Uani 1 1 d . . . C11 C 1.00910(16) 0.19548(17) 0.4804(6) 0.085(2) Uani 1 1 d . . . H11 H 1.0273 0.2177 0.4843 0.102 Uiso 1 1 calc R . . O12 O 0.93936(9) 0.08673(9) 0.8522(3) 0.0725(11) Uani 1 1 d . . . H12 H 0.9293 0.0812 0.7932 0.087 Uiso 1 1 calc R . . C12 C 1.00500(14) 0.17282(17) 0.5598(5) 0.0702(16) Uani 1 1 d . . . O13 O 1.0229(3) 0.2771(3) 0.1599(9) 0.134(4) Uiso 0.50 1 d P . . C13 C 0.97743(15) 0.14090(15) 0.5530(5) 0.0674(15) Uani 1 1 d . . . C14 C 1.03005(15) 0.18200(17) 0.6504(5) 0.088(2) Uani 1 1 d . . . H14A H 1.0504 0.2034 0.6331 0.106 Uiso 1 1 calc R . . H14B H 1.0365 0.1646 0.6566 0.106 Uiso 1 1 calc R . . C15 C 1.01613(13) 0.18537(16) 0.7578(5) 0.0734(17) Uani 1 1 d . . . C16 C 1.01372(14) 0.21356(15) 0.7812(6) 0.0748(17) Uani 1 1 d . . . H16 H 1.0216 0.2311 0.7298 0.090 Uiso 1 1 calc R . . C17 C 1.00063(16) 0.21702(15) 0.8736(6) 0.0806(18) Uani 1 1 d . . . C18 C 0.98954(14) 0.19201(16) 0.9485(5) 0.0736(17) Uani 1 1 d . . . H18 H 0.9807 0.1947 1.0141 0.088 Uiso 1 1 calc R . . C19 C 0.99074(12) 0.16264(13) 0.9320(5) 0.0571(14) Uani 1 1 d . . . C20 C 1.00559(13) 0.16063(16) 0.8370(5) 0.0690(16) Uani 1 1 d . . . C21 C 0.97514(14) 0.13424(15) 1.0115(5) 0.0746(16) Uani 1 1 d . . . H21A H 0.9835 0.1186 0.9977 0.089 Uiso 1 1 calc R . . H21B H 0.9819 0.1432 1.0850 0.089 Uiso 1 1 calc R . . C22 C 0.93827(14) 0.11599(13) 1.0039(5) 0.0656(15) Uani 1 1 d . . . C23 C 0.91957(15) 0.12055(13) 1.0822(5) 0.0656(15) Uani 1 1 d . . . H23 H 0.9305 0.1355 1.1399 0.079 Uiso 1 1 calc R . . C24 C 0.88406(16) 0.10286(15) 1.0766(5) 0.0683(16) Uani 1 1 d . . . C25 C 0.86846(15) 0.08134(13) 0.9929(5) 0.0658(15) Uani 1 1 d . . . H25 H 0.8448 0.0702 0.9891 0.079 Uiso 1 1 calc R . . C26 C 0.88553(14) 0.07518(13) 0.9143(5) 0.0611(14) Uani 1 1 d . . . C27 C 0.92136(14) 0.09254(13) 0.9229(5) 0.0616(15) Uani 1 1 d . . . C28 C 0.86803(14) 0.05091(14) 0.8249(5) 0.0712(16) Uani 1 1 d . . . H28A H 0.8442 0.0364 0.8439 0.085 Uiso 1 1 calc R . . H28B H 0.8780 0.0365 0.8158 0.085 Uiso 1 1 calc R . . C29 C 0.83067(18) 0.11521(18) 0.5871(6) 0.0454(18) Uani 0.65 1 d P . . C30 C 0.89853(15) 0.02404(14) 0.6186(6) 0.0850(18) Uani 1 1 d U . . H30A H 0.8964 0.0232 0.5395 0.102 Uiso 1 1 calc R . . H30B H 0.8761 0.0098 0.6501 0.102 Uiso 1 1 calc R . . C31 C 0.92216(18) 0.01197(16) 0.6537(7) 0.100(2) Uani 1 1 d U . . H31A H 0.9241 0.0136 0.7329 0.119 Uiso 1 1 calc R . . H31B H 0.9120 -0.0119 0.6346 0.119 Uiso 1 1 calc R . . C32 C 0.95643(17) 0.03024(18) 0.6070(7) 0.114(3) Uani 1 1 d U . . H32A H 0.9551 0.0277 0.5288 0.171 Uiso 1 1 calc R . . H32B H 0.9698 0.0211 0.6362 0.171 Uiso 1 1 calc R . . H32C H 0.9669 0.0540 0.6253 0.171 Uiso 1 1 calc R . . C33 C 0.99150(19) 0.2084(2) 0.3052(8) 0.096(2) Uani 1 1 d . . . C34 C 0.9972(3) 0.2467(3) 0.8863(10) 0.035(3) Uiso 0.35 1 d P . . C35 C 1.03892(18) 0.1353(2) 0.8519(8) 0.119(3) Uani 1 1 d U . . H35A H 1.0420 0.1400 0.9298 0.143 Uiso 1 1 calc R . . H35B H 1.0579 0.1536 0.8133 0.143 Uiso 1 1 calc R . . C36 C 1.0371(2) 0.1022(2) 0.8276(8) 0.128(3) Uani 1 1 d U . . H36A H 1.0335 0.0979 0.7496 0.154 Uiso 1 1 calc R . . H36B H 1.0590 0.1044 0.8449 0.154 Uiso 1 1 calc R . . C37 C 1.0108(3) 0.0723(2) 0.8853(9) 0.154(4) Uani 1 1 d U . . H37A H 1.0157 0.0746 0.9623 0.232 Uiso 1 1 calc R . . H37B H 1.0103 0.0522 0.8581 0.232 Uiso 1 1 calc R . . H37C H 0.9890 0.0705 0.8734 0.232 Uiso 1 1 calc R . . C38 C 0.8655(2) 0.10681(18) 1.1632(7) 0.092(2) Uani 1 1 d . . . C39 C 0.91374(18) 0.19615(18) 0.6300(6) 0.091(2) Uani 1 1 d . A 1 H39 H 0.9169 0.2085 0.5659 0.109 Uiso 1 1 calc R A 1 C40 C 0.93255(16) 0.18150(16) 0.6473(6) 0.0823(18) Uani 1 1 d . A 1 H40 H 0.9489 0.1840 0.5963 0.099 Uiso 1 1 calc R A 1 C41 C 0.92793(15) 0.16338(15) 0.7371(6) 0.0820(19) Uani 1 1 d . A 1 H41 H 0.9403 0.1523 0.7483 0.098 Uiso 1 1 calc R A 1 C42 C 0.90546(17) 0.16114(16) 0.8107(6) 0.096(2) Uani 1 1 d . A 1 H42 H 0.9022 0.1489 0.8751 0.115 Uiso 1 1 calc R A 1 C43 C 0.88731(16) 0.17693(18) 0.7909(7) 0.092(2) Uani 1 1 d . A 1 H43 H 0.8718 0.1758 0.8430 0.111 Uiso 1 1 calc R A 1 N44 N 0.89117(14) 0.19365(15) 0.7005(5) 0.0906(16) Uani 1 1 d . A 1 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 0.071(3) 0.091(4) 0.046(3) 0.024(3) 0.016(3) 0.074(3) C1 0.062(3) 0.044(3) 0.069(4) 0.001(3) -0.011(3) 0.023(3) O2 0.103(5) 0.129(5) 0.043(3) 0.028(3) 0.014(3) 0.099(4) C2 0.056(3) 0.065(3) 0.067(4) -0.002(3) -0.005(3) 0.026(3) O3 0.138(5) 0.141(5) 0.091(4) 0.002(4) -0.004(4) 0.061(4) C3 0.063(3) 0.059(3) 0.059(4) -0.007(3) -0.009(3) 0.031(3) O4 0.124(4) 0.104(4) 0.133(4) 0.037(3) 0.027(4) 0.052(4) C4 0.060(3) 0.064(3) 0.072(4) -0.006(3) -0.002(3) 0.035(3) C5 0.051(3) 0.054(3) 0.068(4) -0.005(3) 0.001(3) 0.023(3) C6 0.045(3) 0.054(3) 0.080(4) -0.010(3) -0.012(3) 0.021(3) O7 0.107(4) 0.181(6) 0.127(5) -0.044(5) 0.010(4) 0.058(4) C7 0.059(3) 0.063(4) 0.063(4) -0.022(3) -0.003(3) 0.019(3) O8 0.088(4) 0.143(5) 0.142(5) -0.024(4) 0.001(3) 0.061(3) C8 0.071(4) 0.089(4) 0.058(4) -0.014(3) 0.004(3) 0.056(4) O9 0.061(2) 0.051(2) 0.119(3) -0.021(2) -0.031(2) 0.0313(19) C9 0.070(4) 0.095(5) 0.053(3) -0.005(3) 0.000(3) 0.056(4) O10 0.056(2) 0.071(3) 0.090(3) -0.016(2) -0.013(2) 0.024(2) C10 0.071(4) 0.069(4) 0.080(5) 0.004(4) 0.016(4) 0.034(4) O11 0.058(2) 0.070(2) 0.114(3) -0.032(2) -0.028(2) 0.042(2) C11 0.061(4) 0.073(4) 0.108(6) -0.007(4) 0.019(4) 0.023(3) O12 0.068(2) 0.074(3) 0.075(3) -0.008(2) -0.010(2) 0.036(2) C12 0.049(3) 0.085(5) 0.072(4) -0.008(4) 0.011(3) 0.030(3) C13 0.075(4) 0.068(4) 0.066(4) 0.004(3) 0.013(3) 0.041(4) C14 0.057(4) 0.097(5) 0.093(5) -0.007(4) 0.015(4) 0.025(3) C15 0.048(3) 0.070(4) 0.083(4) 0.004(4) 0.003(3) 0.014(3) C16 0.058(4) 0.058(4) 0.096(5) 0.008(3) 0.006(3) 0.020(3) C17 0.079(4) 0.054(4) 0.103(5) -0.001(4) 0.001(4) 0.029(3) C18 0.058(3) 0.087(5) 0.082(4) -0.026(4) -0.014(3) 0.041(3) C19 0.044(3) 0.054(3) 0.077(4) -0.006(3) -0.016(3) 0.027(3) C20 0.045(3) 0.083(4) 0.073(4) -0.021(3) -0.007(3) 0.029(3) C21 0.062(4) 0.075(4) 0.076(4) -0.002(3) -0.011(3) 0.027(3) C22 0.063(4) 0.058(3) 0.073(4) -0.004(3) -0.013(3) 0.028(3) C23 0.073(4) 0.057(3) 0.062(4) -0.003(3) -0.017(3) 0.029(3) C24 0.080(4) 0.069(4) 0.064(4) 0.006(3) 0.011(3) 0.043(3) C25 0.069(4) 0.048(3) 0.077(4) 0.008(3) -0.008(3) 0.027(3) C26 0.070(4) 0.051(3) 0.068(4) 0.006(3) -0.012(3) 0.034(3) C27 0.060(4) 0.049(3) 0.067(4) 0.015(3) -0.009(3) 0.020(3) C28 0.057(3) 0.058(3) 0.082(4) 0.002(3) -0.018(3) 0.017(3) C29 0.058(5) 0.057(5) 0.043(5) -0.013(4) -0.012(4) 0.045(4) C30 0.077(4) 0.059(4) 0.123(5) -0.016(3) -0.020(4) 0.037(3) C31 0.097(4) 0.061(4) 0.146(5) -0.005(4) -0.035(4) 0.043(3) C32 0.077(5) 0.093(5) 0.186(8) -0.015(5) -0.010(5) 0.054(4) C33 0.072(5) 0.097(6) 0.106(7) -0.009(5) 0.021(5) 0.033(5) C35 0.086(4) 0.131(6) 0.172(7) -0.066(5) -0.047(4) 0.079(4) C36 0.101(5) 0.135(6) 0.191(7) -0.074(5) -0.051(5) 0.091(5) C37 0.137(7) 0.123(7) 0.241(11) -0.022(7) -0.063(7) 0.093(6) C38 0.091(6) 0.081(5) 0.107(6) -0.007(4) -0.011(5) 0.044(4) C39 0.101(5) 0.116(6) 0.083(5) -0.011(4) 0.009(4) 0.074(5) C40 0.081(4) 0.070(4) 0.106(5) -0.006(4) 0.007(4) 0.045(4) C41 0.059(4) 0.071(4) 0.126(6) 0.001(4) -0.002(4) 0.040(3) C42 0.083(5) 0.086(5) 0.127(6) 0.029(4) 0.006(5) 0.050(4) C43 0.081(4) 0.115(6) 0.106(6) 0.014(5) 0.010(4) 0.067(4) N44 0.094(4) 0.106(4) 0.091(4) -0.003(3) -0.007(3) 0.065(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C29 1.317(8) . ? O1 H1S 0.8400 . ? C1 C6 1.382(8) . ? C1 C2 1.398(7) . ? C1 C28 1.555(7) . ? O2 C29 1.182(8) . ? C2 C3 1.373(7) . ? C2 H2 0.9500 . ? O3 C33 1.213(9) . ? C3 C4 1.376(7) . ? C3 C29 1.543(9) . ? O4 C33 1.319(9) . ? O4 H4S 0.8400 . ? C4 C5 1.346(7) . ? C4 H4 0.9500 . ? O5 C34 1.255(13) . ? C5 C6 1.375(8) . ? C5 C7 1.530(7) . ? O6 C34 1.107(13) . ? O6 H6S 0.8400 . ? C6 O9 1.418(6) . ? O7 C38 1.260(9) . ? C7 C8 1.523(8) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? O8 C38 1.314(8) . ? O8 H8S 0.8400 . ? C8 C9 1.374(8) . ? C8 C13 1.421(8) . ? O9 C30 1.450(6) . ? C9 C10 1.356(8) . ? C9 H9 0.9500 . ? O10 C13 1.361(7) . ? O10 H10 0.8400 . ? C10 C11 1.404(9) . ? C10 C33 1.459(10) . ? O11 C20 1.372(7) . ? O11 C35 1.472(7) . ? C11 C12 1.384(9) . ? C11 H11 0.9500 . ? O12 C27 1.329(7) . ? O12 H12 0.8400 . ? C12 C13 1.390(8) . ? C12 C14 1.519(8) . ? C14 C15 1.527(8) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.395(8) . ? C15 C20 1.402(8) . ? C16 C17 1.349(9) . ? C16 H16 0.9500 . ? C17 C18 1.371(9) . ? C17 C34 1.469(13) . ? C18 C19 1.403(7) . ? C18 H18 0.9500 . ? C19 C20 1.396(7) . ? C19 C21 1.511(8) . ? C21 C22 1.481(8) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 C23 1.389(8) . ? C22 C27 1.400(8) . ? C23 C24 1.425(8) . ? C23 H23 0.9500 . ? C24 C25 1.372(8) . ? C24 C38 1.446(9) . ? C25 C26 1.375(8) . ? C25 H25 0.9500 . ? C26 C27 1.440(7) . ? C26 C28 1.500(8) . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C30 C31 1.520(8) . ? C30 H30A 0.9900 . ? C30 H30B 0.9900 . ? C31 C32 1.493(10) . ? C31 H31A 0.9900 . ? C31 H31B 0.9900 . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? C35 C36 1.522(10) . ? C35 H35A 0.9900 . ? C35 H35B 0.9900 . ? C36 C37 1.493(13) . ? C36 H36A 0.9900 . ? C36 H36B 0.9900 . ? C37 H37A 0.9800 . ? C37 H37B 0.9800 . ? C37 H37C 0.9800 . ? C39 N44 1.325(8) . ? C39 C40 1.362(9) . ? C39 H39 0.9500 . ? C40 C41 1.350(9) . ? C40 H40 0.9500 . ? C41 C42 1.352(9) . ? C41 H41 0.9500 . ? C42 C43 1.384(9) . ? C42 H42 0.9500 . ? C43 N44 1.328(8) . ? C43 H43 0.9500 . ? 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 C29 O1 H1S 109.5 . . ? C6 C1 C2 117.4(5) . . ? C6 C1 C28 122.8(5) . . ? C2 C1 C28 119.8(5) . . ? C3 C2 C1 119.9(5) . . ? C3 C2 H2 120.0 . . ? C1 C2 H2 120.0 . . ? C2 C3 C4 119.9(5) . . ? C2 C3 C29 119.8(6) . . ? C4 C3 C29 120.3(6) . . ? C33 O4 H4S 109.5 . . ? C5 C4 C3 121.7(6) . . ? C5 C4 H4 119.1 . . ? C3 C4 H4 119.1 . . ? C4 C5 C6 118.2(5) . . ? C4 C5 C7 121.4(5) . . ? C6 C5 C7 120.4(5) . . ? C34 O6 H6S 109.5 . . ? C5 C6 C1 122.6(5) . . ? C5 C6 O9 120.9(5) . . ? C1 C6 O9 116.2(5) . . ? C8 C7 C5 112.0(4) . . ? C8 C7 H7A 109.2 . . ? C5 C7 H7A 109.2 . . ? C8 C7 H7B 109.2 . . ? C5 C7 H7B 109.2 . . ? H7A C7 H7B 107.9 . . ? C38 O8 H8S 109.5 . . ? C9 C8 C13 116.9(6) . . ? C9 C8 C7 121.8(5) . . ? C13 C8 C7 121.3(5) . . ? C6 O9 C30 113.5(4) . . ? C10 C9 C8 122.5(6) . . ? C10 C9 H9 118.7 . . ? C8 C9 H9 118.7 . . ? C13 O10 H10 109.5 . . ? C9 C10 C11 119.8(6) . . ? C9 C10 C33 118.0(7) . . ? C11 C10 C33 122.2(7) . . ? C20 O11 C35 112.6(4) . . ? C12 C11 C10 120.6(6) . . ? C12 C11 H11 119.7 . . ? C10 C11 H11 119.7 . . ? C27 O12 H12 109.5 . . ? C11 C12 C13 117.8(6) . . ? C11 C12 C14 121.5(6) . . ? C13 C12 C14 120.6(6) . . ? O10 C13 C12 120.9(6) . . ? O10 C13 C8 116.8(5) . . ? C12 C13 C8 122.2(6) . . ? C12 C14 C15 112.3(5) . . ? C12 C14 H14A 109.2 . . ? C15 C14 H14A 109.2 . . ? C12 C14 H14B 109.2 . . ? C15 C14 H14B 109.2 . . ? H14A C14 H14B 107.9 . . ? C16 C15 C20 117.3(6) . . ? C16 C15 C14 120.9(6) . . ? C20 C15 C14 121.8(6) . . ? C17 C16 C15 122.7(6) . . ? C17 C16 H16 118.7 . . ? C15 C16 H16 118.7 . . ? C16 C17 C18 118.9(6) . . ? C16 C17 C34 117.9(7) . . ? C18 C17 C34 123.1(8) . . ? C17 C18 C19 122.6(6) . . ? C17 C18 H18 118.7 . . ? C19 C18 H18 118.7 . . ? C20 C19 C18 116.6(6) . . ? C20 C19 C21 122.4(5) . . ? C18 C19 C21 120.9(5) . . ? O11 C20 C19 119.4(6) . . ? O11 C20 C15 118.7(5) . . ? C19 C20 C15 121.7(6) . . ? C22 C21 C19 111.5(5) . . ? C22 C21 H21A 109.3 . . ? C19 C21 H21A 109.3 . . ? C22 C21 H21B 109.3 . . ? C19 C21 H21B 109.3 . . ? H21A C21 H21B 108.0 . . ? C23 C22 C27 118.4(5) . . ? C23 C22 C21 119.7(5) . . ? C27 C22 C21 121.7(6) . . ? C22 C23 C24 120.4(5) . . ? C22 C23 H23 119.8 . . ? C24 C23 H23 119.8 . . ? C25 C24 C23 119.4(5) . . ? C25 C24 C38 122.0(6) . . ? C23 C24 C38 118.5(6) . . ? C24 C25 C26 123.0(6) . . ? C24 C25 H25 118.5 . . ? C26 C25 H25 118.5 . . ? C25 C26 C27 116.9(5) . . ? C25 C26 C28 122.3(5) . . ? C27 C26 C28 120.9(5) . . ? O12 C27 C22 118.1(5) . . ? O12 C27 C26 120.1(5) . . ? C22 C27 C26 121.8(6) . . ? C26 C28 C1 111.6(4) . . ? C26 C28 H28A 109.3 . . ? C1 C28 H28A 109.3 . . ? C26 C28 H28B 109.3 . . ? C1 C28 H28B 109.3 . . ? H28A C28 H28B 108.0 . . ? O2 C29 O1 126.4(6) . . ? O2 C29 C3 120.8(6) . . ? O1 C29 C3 112.7(6) . . ? O9 C30 C31 106.5(5) . . ? O9 C30 H30A 110.4 . . ? C31 C30 H30A 110.4 . . ? O9 C30 H30B 110.4 . . ? C31 C30 H30B 110.4 . . ? H30A C30 H30B 108.6 . . ? C32 C31 C30 115.8(6) . . ? C32 C31 H31A 108.3 . . ? C30 C31 H31A 108.3 . . ? C32 C31 H31B 108.3 . . ? C30 C31 H31B 108.3 . . ? H31A C31 H31B 107.4 . . ? C31 C32 H32A 109.5 . . ? C31 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C31 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? O3 C33 O4 121.0(8) . . ? O3 C33 C10 124.5(8) . . ? O4 C33 C10 114.3(8) . . ? O6 C34 O5 120.9(12) . . ? O6 C34 C17 120.1(11) . . ? O5 C34 C17 119.0(10) . . ? O11 C35 C36 107.3(5) . . ? O11 C35 H35A 110.3 . . ? C36 C35 H35A 110.3 . . ? O11 C35 H35B 110.3 . . ? C36 C35 H35B 110.3 . . ? H35A C35 H35B 108.5 . . ? C37 C36 C35 116.5(8) . . ? C37 C36 H36A 108.2 . . ? C35 C36 H36A 108.2 . . ? C37 C36 H36B 108.2 . . ? C35 C36 H36B 108.2 . . ? H36A C36 H36B 107.3 . . ? C36 C37 H37A 109.5 . . ? C36 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? C36 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? O7 C38 O8 118.9(7) . . ? O7 C38 C24 124.9(7) . . ? O8 C38 C24 116.2(7) . . ? N44 C39 C40 121.6(7) . . ? N44 C39 H39 119.2 . . ? C40 C39 H39 119.2 . . ? C41 C40 C39 119.9(7) . . ? C41 C40 H40 120.0 . . ? C39 C40 H40 120.0 . . ? C40 C41 C42 119.2(6) . . ? C40 C41 H41 120.4 . . ? C42 C41 H41 120.4 . . ? C41 C42 C43 119.0(7) . . ? C41 C42 H42 120.5 . . ? C43 C42 H42 120.5 . . ? N44 C43 C42 121.2(7) . . ? N44 C43 H43 119.4 . . ? C42 C43 H43 119.4 . . ? C39 N44 C43 119.0(6) . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.994 _refine_diff_density_min -0.307 _refine_diff_density_rms 0.093 # Attachment '5new.CIF' data_ST07 _database_code_depnum_ccdc_archive 'CCDC 731799' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common DiOEtCal4 _chemical_melting_point ? _chemical_formula_moiety 'C32 H32 O4' _chemical_formula_sum 'C32 H32 O4' _chemical_formula_weight 480.58 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbcn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y, z-1/2' _cell_length_a 16.3207(7) _cell_length_b 19.5389(9) _cell_length_c 17.1880(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5481.1(4) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used . _cell_measurement_theta_min . _cell_measurement_theta_max . _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.80 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.165 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2048 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9149 _exptl_absorpt_correction_T_max 0.9777 _exptl_absorpt_process_details Bruker-SADABS _exptl_special_details ; Data were corrected for decay and absorption using the program SADABS based on the method of R.H. Blessing (Acta Cryst. A51, 33-38, 1995). ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker X8 APEX II diffractometer' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 42418 _diffrn_reflns_av_R_equivalents 0.0500 _diffrn_reflns_av_sigmaI/netI 0.0360 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.40 _diffrn_reflns_theta_max 26.38 _reflns_number_total 5598 _reflns_number_gt 4282 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement 'SAINT (Bruker, 1998)' _computing_data_reduction 'SAINT (Bruker, 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour 2001)' _computing_publication_material 'local program' _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. The routine SQUEEZE was applied to the data in order to remove diffuse electron density associated with a badly disordered chloroform molecule. ; _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^)+(0.0619P)^2^+2.3353P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5598 _refine_ls_number_parameters 327 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0679 _refine_ls_R_factor_gt 0.0492 _refine_ls_wR_factor_ref 0.1292 _refine_ls_wR_factor_gt 0.1208 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.000 0.121 0.250 145 64 ' ' 2 0.000 0.879 0.750 145 64 ' ' 3 0.500 0.621 0.250 145 64 ' ' 4 0.500 0.379 0.750 145 64 ' ' #_platon_squeeze_details 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 0.22840(10) 0.56010(9) 0.11117(10) 0.0212(4) Uani 1 1 d . . . O2 O 0.20684(7) 0.34877(7) 0.04424(7) 0.0278(3) Uani 1 1 d . . . H2 H 0.1779 0.3503 0.0846 0.033 Uiso 1 1 calc R . . C2 C 0.27868(10) 0.60167(9) 0.06490(10) 0.0215(4) Uani 1 1 d . . . O3 O 0.12825(7) 0.39484(6) 0.16837(7) 0.0223(3) Uani 1 1 d . . . C3 C 0.25877(11) 0.67033(9) 0.05813(11) 0.0257(4) Uani 1 1 d . . . H3 H 0.2917 0.6990 0.0263 0.031 Uiso 1 1 calc R . . O4 O 0.35204(7) 0.42754(6) 0.03216(7) 0.0246(3) Uani 1 1 d . . . C4 C 0.19180(11) 0.69842(10) 0.09676(11) 0.0275(4) Uani 1 1 d . . . H4 H 0.1801 0.7459 0.0926 0.033 Uiso 1 1 calc R . . O5 O 0.24456(8) 0.49272(7) 0.12501(7) 0.0286(3) Uani 1 1 d . . . H5 H 0.2877 0.4814 0.1017 0.034 Uiso 1 1 calc R . . C5 C 0.14236(11) 0.65598(9) 0.14150(10) 0.0244(4) Uani 1 1 d . . . H5A H 0.0964 0.6748 0.1678 0.029 Uiso 1 1 calc R . . C6 C 0.15896(10) 0.58649(9) 0.14849(10) 0.0214(4) Uani 1 1 d . . . C7 C 0.10423(11) 0.54023(9) 0.19688(10) 0.0233(4) Uani 1 1 d . . . H7A H 0.0716 0.5689 0.2329 0.028 Uiso 1 1 calc R . . H7B H 0.1392 0.5098 0.2288 0.028 Uiso 1 1 calc R . . C8 C 0.04585(10) 0.49624(9) 0.14846(10) 0.0214(4) Uani 1 1 d . . . C9 C -0.02411(10) 0.52500(9) 0.11436(10) 0.0226(4) Uani 1 1 d . . . H9 H -0.0359 0.5720 0.1227 0.027 Uiso 1 1 calc R . . C10 C -0.07618(10) 0.48639(10) 0.06884(10) 0.0236(4) Uani 1 1 d . . . H10 H -0.1240 0.5067 0.0475 0.028 Uiso 1 1 calc R . . C11 C -0.05911(10) 0.41804(10) 0.05408(10) 0.0232(4) Uani 1 1 d . . . H11 H -0.0946 0.3921 0.0218 0.028 Uiso 1 1 calc R . . C12 C 0.01023(10) 0.38731(9) 0.08662(10) 0.0223(4) Uani 1 1 d . . . C13 C 0.05961(10) 0.42679(9) 0.13541(9) 0.0207(4) Uani 1 1 d . . . C14 C 0.03158(11) 0.31347(9) 0.06741(10) 0.0251(4) Uani 1 1 d . . . H14A H -0.0197 0.2865 0.0642 0.030 Uiso 1 1 calc R . . H14B H 0.0648 0.2943 0.1104 0.030 Uiso 1 1 calc R . . C15 C 0.07873(11) 0.30529(9) -0.00860(10) 0.0229(4) Uani 1 1 d . . . C16 C 0.04029(11) 0.27771(9) -0.07351(11) 0.0272(4) Uani 1 1 d . . . H16 H -0.0152 0.2634 -0.0695 0.033 Uiso 1 1 calc R . . C17 C 0.08063(12) 0.27041(10) -0.14398(11) 0.0305(4) Uani 1 1 d . . . H17 H 0.0530 0.2516 -0.1877 0.037 Uiso 1 1 calc R . . C18 C 0.16194(12) 0.29093(9) -0.14990(11) 0.0275(4) Uani 1 1 d . . . H18 H 0.1895 0.2868 -0.1984 0.033 Uiso 1 1 calc R . . C19 C 0.20350(11) 0.31726(9) -0.08638(11) 0.0246(4) Uani 1 1 d . . . C20 C 0.16150(11) 0.32461(9) -0.01566(10) 0.0221(4) Uani 1 1 d . . . C21 C 0.29310(11) 0.33824(10) -0.09133(11) 0.0268(4) Uani 1 1 d . . . H21A H 0.3188 0.3152 -0.1364 0.032 Uiso 1 1 calc R . . H21B H 0.3219 0.3228 -0.0438 0.032 Uiso 1 1 calc R . . C22 C 0.30353(10) 0.41526(10) -0.09981(10) 0.0246(4) Uani 1 1 d . . . C23 C 0.28210(11) 0.44694(10) -0.16953(11) 0.0279(4) Uani 1 1 d . . . H23 H 0.2634 0.4197 -0.2117 0.033 Uiso 1 1 calc R . . C24 C 0.28748(12) 0.51709(10) -0.17862(11) 0.0290(4) Uani 1 1 d . . . H24 H 0.2743 0.5375 -0.2272 0.035 Uiso 1 1 calc R . . C25 C 0.31214(11) 0.55764(10) -0.11655(11) 0.0274(4) Uani 1 1 d . . . H25 H 0.3145 0.6059 -0.1226 0.033 Uiso 1 1 calc R . . C26 C 0.33343(10) 0.52818(10) -0.04537(10) 0.0235(4) Uani 1 1 d . . . C27 C 0.33134(10) 0.45696(9) -0.03927(10) 0.0233(4) Uani 1 1 d . . . C28 C 0.35414(10) 0.57373(9) 0.02369(10) 0.0235(4) Uani 1 1 d . . . H28A H 0.3872 0.5472 0.0614 0.028 Uiso 1 1 calc R . . H28B H 0.3880 0.6126 0.0054 0.028 Uiso 1 1 calc R . . C29 C 0.11530(11) 0.36435(10) 0.24410(11) 0.0283(4) Uani 1 1 d . . . H29A H 0.0651 0.3359 0.2437 0.034 Uiso 1 1 calc R . . H29B H 0.1088 0.4005 0.2840 0.034 Uiso 1 1 calc R . . C30 C 0.18887(12) 0.32101(10) 0.26189(11) 0.0313(4) Uani 1 1 d . . . H30A H 0.1895 0.2811 0.2273 0.047 Uiso 1 1 calc R . . H30B H 0.1863 0.3056 0.3161 0.047 Uiso 1 1 calc R . . H30C H 0.2388 0.3480 0.2539 0.047 Uiso 1 1 calc R . . C31 C 0.43734(10) 0.41080(10) 0.04244(11) 0.0284(4) Uani 1 1 d . . . H31A H 0.4719 0.4515 0.0323 0.034 Uiso 1 1 calc R . . H31B H 0.4536 0.3741 0.0059 0.034 Uiso 1 1 calc R . . C32 C 0.44786(13) 0.38736(12) 0.12475(12) 0.0384(5) Uani 1 1 d . . . H32A H 0.4307 0.4239 0.1603 0.058 Uiso 1 1 calc R . . H32B H 0.5056 0.3762 0.1341 0.058 Uiso 1 1 calc R . . H32C H 0.4142 0.3466 0.1337 0.058 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0197(8) 0.0236(9) 0.0203(9) 0.0007(7) 0.0002(7) 0.0032(7) O2 0.0214(6) 0.0362(8) 0.0259(7) -0.0017(5) 0.0055(5) 0.0020(5) C2 0.0166(8) 0.0284(10) 0.0195(9) -0.0001(7) 0.0007(7) 0.0003(7) O3 0.0192(6) 0.0275(7) 0.0203(6) 0.0078(5) 0.0033(5) 0.0065(5) C3 0.0218(9) 0.0266(9) 0.0287(10) 0.0038(8) 0.0022(8) -0.0030(7) O4 0.0156(6) 0.0313(7) 0.0269(7) 0.0046(5) 0.0031(5) 0.0049(5) C4 0.0234(9) 0.0250(9) 0.0341(10) 0.0001(8) -0.0006(8) 0.0008(7) O5 0.0260(7) 0.0292(7) 0.0307(7) 0.0082(6) 0.0125(6) 0.0089(5) C5 0.0204(9) 0.0281(10) 0.0246(9) -0.0039(7) 0.0008(7) 0.0047(7) C6 0.0190(8) 0.0263(9) 0.0190(9) 0.0001(7) -0.0008(7) 0.0020(7) C7 0.0206(9) 0.0296(10) 0.0196(9) 0.0018(7) 0.0044(7) 0.0037(7) C8 0.0188(8) 0.0278(9) 0.0174(8) 0.0044(7) 0.0068(7) 0.0024(7) C9 0.0222(9) 0.0256(9) 0.0201(9) 0.0057(7) 0.0091(7) 0.0050(7) C10 0.0165(8) 0.0340(10) 0.0203(9) 0.0068(7) 0.0047(7) 0.0053(7) C11 0.0193(8) 0.0304(10) 0.0198(9) 0.0050(7) 0.0051(7) 0.0011(7) C12 0.0205(9) 0.0265(9) 0.0200(9) 0.0072(7) 0.0086(7) 0.0018(7) C13 0.0166(8) 0.0288(10) 0.0167(8) 0.0084(7) 0.0058(7) 0.0051(7) C14 0.0235(9) 0.0246(9) 0.0271(10) 0.0049(7) 0.0030(8) 0.0018(7) C15 0.0232(9) 0.0176(9) 0.0279(10) 0.0048(7) 0.0018(7) 0.0052(7) C16 0.0220(9) 0.0241(9) 0.0353(11) 0.0021(8) 0.0013(8) 0.0025(7) C17 0.0296(10) 0.0306(10) 0.0314(10) -0.0044(8) -0.0032(8) 0.0035(8) C18 0.0304(10) 0.0258(10) 0.0262(10) -0.0002(8) 0.0060(8) 0.0075(8) C19 0.0232(9) 0.0200(9) 0.0306(10) 0.0025(7) 0.0042(8) 0.0076(7) C20 0.0233(9) 0.0191(8) 0.0240(9) 0.0018(7) -0.0008(7) 0.0040(7) C21 0.0248(10) 0.0284(10) 0.0273(10) -0.0025(8) 0.0053(8) 0.0082(8) C22 0.0161(8) 0.0305(10) 0.0272(9) -0.0017(8) 0.0076(7) 0.0038(7) C23 0.0246(9) 0.0357(11) 0.0235(10) -0.0024(8) 0.0037(7) 0.0005(8) C24 0.0286(10) 0.0350(11) 0.0235(10) 0.0033(8) 0.0022(8) 0.0012(8) C25 0.0231(9) 0.0296(10) 0.0295(10) 0.0053(8) 0.0045(8) 0.0002(8) C26 0.0137(8) 0.0319(10) 0.0250(9) 0.0008(7) 0.0055(7) 0.0006(7) C27 0.0157(8) 0.0310(10) 0.0231(9) 0.0041(8) 0.0063(7) 0.0033(7) C28 0.0176(8) 0.0276(9) 0.0254(9) 0.0012(7) 0.0020(7) -0.0007(7) C29 0.0286(10) 0.0347(11) 0.0215(9) 0.0118(8) 0.0032(8) 0.0045(8) C30 0.0358(11) 0.0283(10) 0.0298(10) 0.0072(8) -0.0058(9) 0.0050(8) C31 0.0156(9) 0.0311(10) 0.0386(11) 0.0007(8) 0.0025(8) 0.0045(7) C32 0.0311(11) 0.0448(13) 0.0392(12) -0.0006(10) -0.0095(9) 0.0066(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 O5 1.364(2) . ? C1 C6 1.401(2) . ? C1 C2 1.402(2) . ? O2 C20 1.353(2) . ? C2 C3 1.385(3) . ? C2 C28 1.522(2) . ? O3 C13 1.402(2) . ? O3 C29 1.447(2) . ? C3 C4 1.392(3) . ? O4 C27 1.397(2) . ? O4 C31 1.441(2) . ? C4 C5 1.389(3) . ? C5 C6 1.390(2) . ? C6 C7 1.519(2) . ? C7 C8 1.530(3) . ? C8 C13 1.393(2) . ? C8 C9 1.401(2) . ? C9 C10 1.380(3) . ? C10 C11 1.388(3) . ? C11 C12 1.398(2) . ? C12 C13 1.396(3) . ? C12 C14 1.521(2) . ? C14 C15 1.525(2) . ? C15 C16 1.389(3) . ? C15 C20 1.408(2) . ? C16 C17 1.386(3) . ? C17 C18 1.390(3) . ? C18 C19 1.384(3) . ? C19 C20 1.403(2) . ? C19 C21 1.521(3) . ? C21 C22 1.522(3) . ? C22 C23 1.393(3) . ? C22 C27 1.397(3) . ? C23 C24 1.382(3) . ? C24 C25 1.388(3) . ? C25 C26 1.396(3) . ? C26 C27 1.396(3) . ? C26 C28 1.522(3) . ? C29 C30 1.501(3) . ? C31 C32 1.497(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 O5 C1 C6 115.59(15) . . ? O5 C1 C2 123.03(15) . . ? C6 C1 C2 121.34(16) . . ? C3 C2 C1 118.13(16) . . ? C3 C2 C28 119.87(16) . . ? C1 C2 C28 121.99(16) . . ? C13 O3 C29 115.47(12) . . ? C2 C3 C4 121.74(17) . . ? C27 O4 C31 115.76(13) . . ? C5 C4 C3 119.00(17) . . ? C4 C5 C6 121.19(16) . . ? C5 C6 C1 118.54(16) . . ? C5 C6 C7 120.94(15) . . ? C1 C6 C7 120.51(16) . . ? C6 C7 C8 113.75(14) . . ? C13 C8 C9 117.04(17) . . ? C13 C8 C7 122.30(15) . . ? C9 C8 C7 120.66(16) . . ? C10 C9 C8 121.32(17) . . ? C9 C10 C11 120.42(16) . . ? C10 C11 C12 120.18(17) . . ? C13 C12 C11 118.07(16) . . ? C13 C12 C14 121.51(15) . . ? C11 C12 C14 120.41(17) . . ? C8 C13 C12 122.81(15) . . ? C8 C13 O3 119.83(16) . . ? C12 C13 O3 117.26(15) . . ? C12 C14 C15 113.65(14) . . ? C16 C15 C20 117.93(16) . . ? C16 C15 C14 120.06(16) . . ? C20 C15 C14 122.01(16) . . ? C17 C16 C15 121.83(17) . . ? C16 C17 C18 119.20(18) . . ? C19 C18 C17 121.14(17) . . ? C18 C19 C20 118.81(17) . . ? C18 C19 C21 121.80(17) . . ? C20 C19 C21 119.38(17) . . ? O2 C20 C19 115.33(16) . . ? O2 C20 C15 123.56(16) . . ? C19 C20 C15 121.06(16) . . ? C19 C21 C22 112.30(14) . . ? C23 C22 C27 117.58(17) . . ? C23 C22 C21 119.59(17) . . ? C27 C22 C21 122.79(17) . . ? C24 C23 C22 121.45(18) . . ? C23 C24 C25 119.82(18) . . ? C24 C25 C26 120.68(18) . . ? C27 C26 C25 118.09(17) . . ? C27 C26 C28 122.00(16) . . ? C25 C26 C28 119.85(17) . . ? C26 C27 O4 118.06(16) . . ? C26 C27 C22 122.22(17) . . ? O4 C27 C22 119.54(16) . . ? C2 C28 C26 113.15(14) . . ? O3 C29 C30 107.38(14) . . ? O4 C31 C32 107.22(15) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 26.38 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.236 _refine_diff_density_min -0.248 _refine_diff_density_rms 0.044 # Attachment '9Pynew.CIF' data_9Py _database_code_depnum_ccdc_archive 'CCDC 731800' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'DiOEt C4 Tri Acid Py' _chemical_melting_point ? _chemical_formula_moiety 'C35 H32 O10, 0.5(C11 H11 N), 0.5(C6 H6), 1.5(C5 H5 N)' _chemical_formula_sum 'C51 H48 N2 O10' _chemical_formula_weight 848.91 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.517(4) _cell_length_b 12.125(4) _cell_length_c 15.363(5) _cell_angle_alpha 90.829(12) _cell_angle_beta 95.031(10) _cell_angle_gamma 99.029(10) _cell_volume 2109.7(11) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 116 _cell_measurement_theta_min 2.59 _cell_measurement_theta_max 18.39 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.336 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 896 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9638 _exptl_absorpt_correction_T_max 0.9816 _exptl_absorpt_process_details Bruker-SADABS _exptl_special_details ; Data were corrected for decay and absorption using the program SADABS based on the method of R.H. Blessing (Acta Cryst. A51, 33-38, 1995). ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Nonius X8 Apex 2' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15713 _diffrn_reflns_av_R_equivalents 0.0903 _diffrn_reflns_av_sigmaI/netI 0.0876 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 20.69 _reflns_number_total 4253 _reflns_number_gt 2580 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Apex II' _computing_cell_refinement 'SAINT (Bruker, 1998)' _computing_data_reduction 'SAINT (Bruker, 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XSeed (Barbour, 2001)' _computing_publication_material 'local program' _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. The structure contains disordered pyridine molecules that crystallise on the exterior of the calixarene cavity. These have been modeled successfully with the use of numerous restraints (and in one case isotropically), and in all possible cases, the nitrogen positions of these disordered molecules has been identified. Although this is the case, one pyridine was positioned such that there were no obvious intermolecular interactions to identify the N atom position, and therefore all disordered atoms were refined as carbon. Disorder results in short contacts in the chceckcif report. Crystals were weakly diffracting even at long exposure. The result of this is that the data to parameter ratio is slightly low. This is not due to lack of completeness but due to the weakly diffracting nature of the crystals. ; _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^)+(0.1200P)^2^+3.7101P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4253 _refine_ls_number_parameters 638 _refine_ls_number_restraints 253 _refine_ls_R_factor_all 0.1287 _refine_ls_R_factor_gt 0.0727 _refine_ls_wR_factor_ref 0.2306 _refine_ls_wR_factor_gt 0.1860 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.033 _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 O1 O 0.6874(5) 1.0309(6) 0.2716(4) 0.0797(18) Uiso 1 1 d . . . N1 N 1.0150(5) 0.6820(4) 0.5239(4) 0.0327(14) Uani 1 1 d . . . C1 C 0.6605(6) 1.0069(6) 0.5442(5) 0.0353(18) Uani 1 1 d . . . O2 O 0.5824(9) 0.8657(9) 0.2489(7) 0.159(4) Uiso 1 1 d . . . H2S H 0.6301 0.8496 0.2143 0.191 Uiso 1 1 calc R . . C2 C 0.6739(6) 1.0175(6) 0.4556(5) 0.0387(19) Uani 1 1 d . . . H2 H 0.7163 1.0846 0.4357 0.046 Uiso 1 1 calc R . . O3 O 0.5840(4) 0.9055(3) 0.6588(3) 0.0325(11) Uani 1 1 d . . . H3 H 0.5449 0.8437 0.6700 0.039 Uiso 1 1 calc R . . C3 C 0.6262(6) 0.9317(7) 0.3950(4) 0.0358(18) Uani 1 1 d . . . O4 O 0.7754(4) 0.4649(4) 0.4550(3) 0.0377(12) Uani 1 1 d . . . C4 C 0.5655(6) 0.8349(6) 0.4248(4) 0.0312(17) Uani 1 1 d . . . H4 H 0.5344 0.7757 0.3842 0.037 Uiso 1 1 calc R . . O5 O 0.8608(4) 0.4119(4) 0.5805(3) 0.0414(13) Uani 1 1 d . . . H5S H 0.8981 0.3792 0.5462 0.050 Uiso 1 1 calc R . . C5 C 0.5482(5) 0.8212(5) 0.5120(5) 0.0309(17) Uani 1 1 d . . . O6 O 0.5027(4) 0.7002(3) 0.7297(3) 0.0316(11) Uani 1 1 d . . . C6 C 0.5968(5) 0.9091(5) 0.5719(5) 0.0301(17) Uani 1 1 d . . . O7 O 1.1053(9) 0.5406(10) 0.9451(7) 0.150(3) Uani 1 1 d U . . C7 C 0.6354(7) 0.9456(7) 0.3035(6) 0.057(2) Uani 1 1 d . . . O8 O 1.1999(6) 0.6874(6) 0.9821(4) 0.080(2) Uani 1 1 d U . . H8S H 1.2452 0.6421 0.9979 0.096 Uiso 1 1 calc R . . C8 C 0.4805(6) 0.7140(5) 0.5432(4) 0.0340(17) Uani 1 1 d . . . H8A H 0.4374 0.6700 0.4922 0.041 Uiso 1 1 calc R . . H8B H 0.4217 0.7321 0.5822 0.041 Uiso 1 1 calc R . . O9 O 0.7144(4) 0.8304(4) 0.8311(3) 0.0365(12) Uani 1 1 d . . . H9 H 0.7308 0.9004 0.8335 0.044 Uiso 1 1 calc R . . C9 C 0.5625(5) 0.6442(5) 0.5920(4) 0.0273(16) Uani 1 1 d . . . O10 O 0.7350(4) 1.0560(4) 0.7947(3) 0.0447(13) Uani 1 1 d . . . C10 C 0.6317(5) 0.5838(5) 0.5460(4) 0.0286(17) Uani 1 1 d . . . H10 H 0.6229 0.5818 0.4839 0.034 Uiso 1 1 calc R . . C11 C 0.7137(5) 0.5261(5) 0.5896(5) 0.0284(17) Uani 1 1 d . . . C12 C 0.7276(6) 0.5308(5) 0.6799(5) 0.0321(17) Uani 1 1 d . . . H12 H 0.7844 0.4920 0.7093 0.039 Uiso 1 1 calc R . . C13 C 0.6607(6) 0.5909(5) 0.7296(4) 0.0302(17) Uani 1 1 d . . . C14 C 0.5742(5) 0.6430(5) 0.6821(4) 0.0285(17) Uani 1 1 d . . . C15 C 0.7856(6) 0.4644(5) 0.5351(5) 0.0329(17) Uani 1 1 d . . . C16 C 0.6811(6) 0.5983(5) 0.8275(4) 0.0319(17) Uani 1 1 d . . . H16A H 0.6793 0.5220 0.8501 0.038 Uiso 1 1 calc R . . H16B H 0.6160 0.6303 0.8511 0.038 Uiso 1 1 calc R . . C17 C 0.7972(6) 0.6690(6) 0.8602(4) 0.0306(17) Uani 1 1 d . . . C18 C 0.8953(6) 0.6201(6) 0.8897(4) 0.0380(19) Uani 1 1 d . . . H18 H 0.8881 0.5410 0.8903 0.046 Uiso 1 1 calc R . . C19 C 1.0039(6) 0.6852(6) 0.9182(4) 0.0316(17) Uani 1 1 d . . . C20 C 1.0152(6) 0.7993(6) 0.9160(4) 0.0375(18) Uani 1 1 d . . . H20 H 1.0894 0.8431 0.9345 0.045 Uiso 1 1 calc R . . C21 C 0.9208(6) 0.8528(5) 0.8875(4) 0.0346(18) Uani 1 1 d . . . C22 C 0.8120(6) 0.7855(6) 0.8601(4) 0.0327(17) Uani 1 1 d . . . C23 C 1.1035(9) 0.6353(8) 0.9518(6) 0.058(2) Uani 1 1 d U . . C24 C 0.9356(6) 0.9796(6) 0.8838(5) 0.0416(19) Uani 1 1 d . . . H24A H 0.8705 1.0062 0.9118 0.050 Uiso 1 1 calc R . . H24B H 1.0108 1.0124 0.9172 0.050 Uiso 1 1 calc R . . C25 C 0.9357(6) 1.0196(5) 0.7905(5) 0.0362(18) Uani 1 1 d . . . C26 C 1.0323(6) 1.0169(5) 0.7443(5) 0.0388(19) Uani 1 1 d . . . H26 H 1.1020 0.9966 0.7730 0.047 Uiso 1 1 calc R . . C27 C 1.0301(6) 1.0431(6) 0.6573(5) 0.0412(19) Uani 1 1 d . . . H27 H 1.0983 1.0426 0.6268 0.049 Uiso 1 1 calc R . . C28 C 0.9266(6) 1.0704(5) 0.6143(5) 0.0390(19) Uani 1 1 d . . . H28 H 0.9240 1.0858 0.5538 0.047 Uiso 1 1 calc R . . C29 C 0.8272(6) 1.0754(5) 0.6593(5) 0.0357(18) Uani 1 1 d . . . C30 C 0.8335(6) 1.0531(5) 0.7477(5) 0.0382(19) Uani 1 1 d . . . C31 C 0.7138(6) 1.1001(6) 0.6103(5) 0.047(2) Uani 1 1 d . . . H31A H 0.7307 1.1712 0.5795 0.056 Uiso 1 1 calc R . . H31B H 0.6558 1.1092 0.6527 0.056 Uiso 1 1 calc R . . C32 C 0.3901(6) 0.6300(6) 0.7411(5) 0.0425(19) Uani 1 1 d . . . H32A H 0.4033 0.5665 0.7785 0.051 Uiso 1 1 calc R . . H32B H 0.3518 0.5997 0.6837 0.051 Uiso 1 1 calc R . . C33 C 0.3127(6) 0.6986(6) 0.7827(5) 0.051(2) Uani 1 1 d . . . H33A H 0.3491 0.7249 0.8409 0.077 Uiso 1 1 calc R . . H33B H 0.2355 0.6532 0.7881 0.077 Uiso 1 1 calc R . . H33C H 0.3025 0.7629 0.7465 0.077 Uiso 1 1 calc R . . C34 C 0.7409(7) 1.1549(6) 0.8513(5) 0.057(2) Uani 1 1 d . . . H34A H 0.8207 1.1725 0.8826 0.068 Uiso 1 1 calc R . . H34B H 0.6833 1.1390 0.8954 0.068 Uiso 1 1 calc R . . C35 C 0.7152(8) 1.2532(6) 0.8011(6) 0.071(3) Uani 1 1 d . . . H35A H 0.7651 1.2634 0.7524 0.106 Uiso 1 1 calc R . . H35B H 0.7315 1.3201 0.8395 0.106 Uiso 1 1 calc R . . H35C H 0.6319 1.2411 0.7781 0.106 Uiso 1 1 calc R . . C36 C 0.9258(6) 0.7327(5) 0.4934(5) 0.0333(18) Uani 1 1 d . . . H36 H 0.9070 0.7321 0.4319 0.040 Uiso 1 1 calc R . . C37 C 0.8597(6) 0.7854(5) 0.5452(5) 0.0347(18) Uani 1 1 d . . . H37 H 0.7977 0.8213 0.5199 0.042 Uiso 1 1 calc R . . C38 C 0.8838(6) 0.7858(5) 0.6334(5) 0.0317(17) Uani 1 1 d . . . H38 H 0.8381 0.8211 0.6705 0.038 Uiso 1 1 calc R . . C39 C 0.9762(6) 0.7339(5) 0.6688(5) 0.0358(18) Uani 1 1 d . . . H39 H 0.9960 0.7339 0.7301 0.043 Uiso 1 1 calc R . . C40 C 1.0380(6) 0.6823(6) 0.6112(5) 0.0372(18) Uani 1 1 d . . . H40 H 1.1000 0.6451 0.6346 0.045 Uiso 1 1 calc R . . C56 C 0.1786(15) 0.3720(16) 0.7243(14) 0.052(4) Uani 0.50 1 d PDU A 2 H56 H 0.1910 0.4132 0.6728 0.063 Uiso 0.50 1 calc PR A 2 C61 C 0.2617(17) 0.3112(16) 0.7600(15) 0.061(4) Uani 0.50 1 d PDU A 2 H61 H 0.3324 0.3108 0.7325 0.073 Uiso 0.50 1 calc PR A 2 C54 C 0.1942(14) 0.2651(17) 0.8247(14) 0.056(3) Uani 0.50 1 d PDU B 1 H54 H 0.2422 0.2123 0.8452 0.067 Uiso 0.50 1 calc PR B 1 C53 C 0.1018(13) 0.2835(13) 0.8682(13) 0.046(3) Uani 0.50 1 d PDU B 1 H53 H 0.0859 0.2429 0.9194 0.055 Uiso 0.50 1 calc PR B 1 C52 C 0.0310(14) 0.3580(11) 0.8411(12) 0.049(3) Uani 0.50 1 d PDU B 1 H52 H -0.0333 0.3690 0.8732 0.059 Uiso 0.50 1 calc PR B 1 C51 C 0.0513(15) 0.4151(13) 0.7705(12) 0.056(3) Uani 0.50 1 d PDU B 1 H51 H 0.0014 0.4673 0.7517 0.067 Uiso 0.50 1 calc PR B 1 C57 C 0.0753(15) 0.3713(12) 0.7662(12) 0.053(3) Uani 0.50 1 d PDU A 2 H57 H 0.0162 0.4122 0.7433 0.063 Uiso 0.50 1 calc PR A 2 C55 C 0.2192(16) 0.3257(16) 0.7476(14) 0.056(4) Uani 0.50 1 d PDU B 1 H55 H 0.2833 0.3158 0.7148 0.067 Uiso 0.50 1 calc PR B 1 N60 N 0.2459(14) 0.2539(15) 0.8310(13) 0.068(3) Uani 0.50 1 d PDU A 2 C59 C 0.1484(15) 0.2565(14) 0.8668(14) 0.057(4) Uani 0.50 1 d PDU A 2 H59 H 0.1388 0.2145 0.9181 0.068 Uiso 0.50 1 calc PR A 2 C58 C 0.0596(16) 0.3111(13) 0.8404(12) 0.054(4) Uani 0.50 1 d PDU A 2 H58 H -0.0091 0.3083 0.8708 0.064 Uiso 0.50 1 calc PR A 2 C65 C 0.488(2) 0.088(2) 1.0563(18) 0.084(5) Uani 0.50 1 d PDU . 1 H65 H 0.4775 0.1487 1.0933 0.101 Uiso 0.50 1 calc PR . 1 C62 C 0.441(3) 0.084(2) 1.0140(16) 0.083(4) Uani 0.50 1 d PDU . 2 H62 H 0.3945 0.1405 1.0250 0.099 Uiso 0.50 1 calc PR . 2 C66 C 0.414(2) 0.064(2) 0.9791(18) 0.085(4) Uani 0.50 1 d PDU C 1 H66 H 0.3549 0.1090 0.9661 0.101 Uiso 0.50 1 calc PR C 1 C63 C 0.440(2) 0.042(2) 0.9288(15) 0.083(4) Uani 0.50 1 d PDU D 2 H63 H 0.4036 0.0732 0.8794 0.100 Uiso 0.50 1 calc PR D 2 C67 C 0.421(2) -0.023(2) 0.9194(14) 0.078(4) Uani 0.50 1 d PDU . 1 H67 H 0.3691 -0.0382 0.8673 0.094 Uiso 0.50 1 calc PR . 1 C64 C 0.497(3) -0.0479(19) 0.9227(17) 0.080(5) Uani 0.50 1 d PDU . 2 H64 H 0.4905 -0.0862 0.8677 0.096 Uiso 0.50 1 calc PR . 2 C71 C 0.6271(13) 0.5109(11) 1.0357(8) 0.039(4) Uiso 0.50 1 d PD E -1 H71 H 0.7035 0.5315 1.0653 0.047 Uiso 0.50 1 calc PR E -1 C68 C 0.4122(17) 0.4606(14) 0.9550(9) 0.059(5) Uiso 0.50 1 d PD E -1 H68 H 0.3365 0.4373 0.9249 0.071 Uiso 0.50 1 calc PR E -1 C72 C 0.5534(13) 0.5903(13) 1.0393(8) 0.040(4) Uiso 0.50 1 d PD E -1 H72 H 0.5788 0.6600 1.0696 0.048 Uiso 0.50 1 calc PR E -1 C69 C 0.4983(15) 0.3899(14) 0.9580(9) 0.061(5) Uiso 0.50 1 d PD E -1 H69 H 0.4769 0.3191 0.9287 0.073 Uiso 0.50 1 calc PR E -1 C73 C 0.4393(14) 0.5637(13) 0.9964(9) 0.048(5) Uiso 0.50 1 d PD E -1 H73 H 0.3841 0.6143 0.9960 0.058 Uiso 0.50 1 calc PR E -1 N70 N 0.6074(13) 0.4134(12) 0.9982(8) 0.066(5) Uiso 0.50 1 d PD E -1 C50 C 0.1425(14) 0.4002(15) 0.7244(14) 0.046(4) Uani 0.50 1 d PDU B 1 H50 H 0.1547 0.4428 0.6736 0.055 Uiso 0.50 1 calc PR B 1 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 N1 0.036(4) 0.029(3) 0.032(4) 0.004(3) 0.004(3) 0.004(3) C1 0.028(4) 0.037(5) 0.043(5) 0.010(4) -0.004(4) 0.016(4) C2 0.026(4) 0.032(4) 0.061(6) 0.025(4) 0.007(4) 0.013(3) O3 0.037(3) 0.029(3) 0.031(3) 0.007(2) -0.002(2) 0.004(2) C3 0.034(4) 0.052(5) 0.029(4) 0.021(4) 0.011(4) 0.023(4) O4 0.037(3) 0.040(3) 0.038(3) -0.002(2) 0.006(2) 0.010(2) C4 0.032(4) 0.038(5) 0.027(5) 0.005(4) 0.005(3) 0.014(3) O5 0.048(3) 0.040(3) 0.042(3) 0.003(2) 0.008(3) 0.022(3) C5 0.017(4) 0.032(4) 0.047(5) 0.005(4) -0.002(3) 0.015(3) O6 0.029(3) 0.030(3) 0.037(3) 0.002(2) 0.010(2) 0.004(2) C6 0.023(4) 0.024(4) 0.044(5) 0.012(4) -0.002(3) 0.008(3) O7 0.138(7) 0.165(9) 0.148(8) 0.027(7) 0.000(6) 0.034(7) C7 0.041(5) 0.050(5) 0.082(7) 0.027(5) 0.011(5) 0.015(4) O8 0.066(4) 0.106(5) 0.068(4) -0.030(4) -0.031(3) 0.043(4) C8 0.036(4) 0.031(4) 0.035(4) -0.006(3) 0.002(3) 0.006(3) O9 0.038(3) 0.027(3) 0.047(3) 0.007(2) 0.001(2) 0.015(2) C9 0.023(4) 0.028(4) 0.031(5) 0.001(3) 0.002(3) 0.001(3) O10 0.043(3) 0.031(3) 0.061(3) -0.009(3) 0.003(3) 0.012(2) C10 0.032(4) 0.027(4) 0.025(4) -0.001(3) 0.004(3) 0.000(3) C11 0.030(4) 0.010(4) 0.045(5) 0.006(3) 0.012(4) -0.003(3) C12 0.027(4) 0.027(4) 0.041(5) 0.009(3) 0.002(4) 0.002(3) C13 0.031(4) 0.024(4) 0.036(4) 0.007(3) 0.011(4) 0.002(3) C14 0.028(4) 0.017(4) 0.041(5) 0.000(3) 0.013(4) 0.001(3) C15 0.031(4) 0.025(4) 0.041(5) 0.005(4) 0.007(4) -0.001(3) C16 0.042(5) 0.030(4) 0.029(4) 0.014(3) 0.011(3) 0.013(3) C17 0.034(4) 0.034(5) 0.028(4) 0.009(3) 0.006(3) 0.017(4) C18 0.056(5) 0.037(4) 0.025(4) 0.009(3) 0.014(4) 0.015(4) C19 0.041(5) 0.033(5) 0.027(4) 0.013(3) 0.002(3) 0.022(4) C20 0.036(4) 0.046(5) 0.030(4) -0.001(4) -0.005(3) 0.010(4) C21 0.042(5) 0.035(5) 0.029(4) -0.004(3) 0.003(4) 0.013(4) C22 0.039(5) 0.040(5) 0.024(4) 0.006(3) 0.004(3) 0.021(4) C23 0.092(7) 0.038(5) 0.050(5) -0.006(5) 0.007(5) 0.032(6) C24 0.037(4) 0.041(5) 0.045(5) -0.006(4) -0.007(4) 0.009(3) C25 0.038(5) 0.025(4) 0.044(5) 0.001(3) -0.005(4) 0.005(3) C26 0.026(4) 0.029(4) 0.058(6) 0.003(4) -0.010(4) -0.001(3) C27 0.032(5) 0.038(5) 0.049(5) 0.015(4) 0.001(4) -0.006(3) C28 0.039(5) 0.028(4) 0.045(5) 0.010(3) -0.003(4) -0.007(3) C29 0.033(5) 0.018(4) 0.053(5) 0.007(4) -0.008(4) 0.003(3) C30 0.036(5) 0.024(4) 0.053(5) 0.005(4) -0.004(4) 0.005(3) C31 0.044(5) 0.027(4) 0.068(5) 0.007(4) -0.006(4) 0.005(4) C32 0.037(5) 0.045(5) 0.044(5) 0.007(4) 0.007(4) 0.000(4) C33 0.042(5) 0.055(5) 0.061(5) 0.005(4) 0.017(4) 0.014(4) C34 0.066(6) 0.031(5) 0.073(6) -0.009(5) -0.003(5) 0.015(4) C35 0.085(7) 0.040(5) 0.087(7) -0.008(5) -0.027(5) 0.027(5) C36 0.037(4) 0.028(4) 0.032(4) 0.006(4) -0.001(4) -0.005(4) C37 0.034(4) 0.027(4) 0.044(5) 0.008(4) 0.011(4) 0.006(3) C38 0.030(4) 0.029(4) 0.038(5) 0.003(3) 0.015(3) 0.004(3) C39 0.042(5) 0.034(4) 0.033(4) 0.002(4) 0.005(4) 0.012(4) C40 0.031(4) 0.034(4) 0.046(5) 0.008(4) -0.001(4) 0.006(3) C56 0.064(8) 0.038(7) 0.055(6) -0.008(6) 0.007(6) 0.003(7) C61 0.058(9) 0.053(7) 0.070(6) -0.012(6) 0.008(7) 0.004(7) C54 0.054(8) 0.043(6) 0.072(6) -0.008(5) 0.003(7) 0.014(6) C53 0.051(8) 0.034(6) 0.060(6) 0.001(6) 0.010(6) 0.024(6) C52 0.054(7) 0.038(7) 0.062(6) 0.001(6) 0.021(6) 0.022(5) C51 0.060(7) 0.046(8) 0.065(6) -0.004(7) 0.006(6) 0.020(6) C57 0.060(7) 0.037(7) 0.063(5) -0.009(6) 0.004(6) 0.017(6) C55 0.056(8) 0.046(6) 0.067(6) -0.014(5) 0.005(6) 0.010(6) N60 0.066(8) 0.052(6) 0.081(6) -0.005(5) -0.012(7) 0.009(7) C59 0.063(9) 0.042(6) 0.064(6) -0.001(6) 0.005(7) 0.004(6) C58 0.059(8) 0.042(7) 0.062(5) -0.005(6) 0.015(6) 0.012(6) C65 0.100(10) 0.079(10) 0.072(11) 0.003(9) 0.004(9) 0.015(9) C62 0.102(10) 0.075(8) 0.072(11) 0.000(9) 0.003(8) 0.018(8) C66 0.102(9) 0.075(8) 0.076(10) 0.005(8) 0.003(8) 0.018(7) C63 0.103(9) 0.075(9) 0.072(8) 0.002(8) 0.004(8) 0.020(8) C67 0.097(9) 0.066(10) 0.073(8) 0.005(8) 0.003(8) 0.020(9) C64 0.102(10) 0.068(10) 0.070(9) 0.006(8) -0.002(9) 0.017(10) C50 0.058(8) 0.035(7) 0.048(5) -0.007(6) 0.015(6) 0.010(6) _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 C7 1.241(9) . ? N1 C36 1.333(8) . ? N1 C40 1.343(8) . ? C1 C6 1.387(9) . ? C1 C2 1.389(10) . ? C1 C31 1.524(10) . ? O2 C7 1.311(12) . ? C2 C3 1.397(10) . ? O3 C6 1.356(8) . ? C3 C4 1.374(9) . ? C3 C7 1.429(11) . ? O4 C15 1.227(8) . ? C4 C5 1.380(9) . ? O5 C15 1.311(8) . ? C5 C6 1.411(9) . ? C5 C8 1.514(9) . ? O6 C14 1.401(7) . ? O6 C32 1.461(8) . ? O7 C23 1.155(11) . ? O8 C23 1.236(11) . ? C8 C9 1.521(9) . ? O9 C22 1.368(7) . ? C9 C14 1.380(9) . ? C9 C10 1.393(9) . ? O10 C30 1.402(8) . ? O10 C34 1.461(8) . ? C10 C11 1.392(9) . ? C11 C12 1.382(9) . ? C11 C15 1.498(9) . ? C12 C13 1.404(9) . ? C13 C14 1.417(9) . ? C13 C16 1.501(9) . ? C16 C17 1.512(9) . ? C17 C22 1.396(9) . ? C17 C18 1.401(9) . ? C18 C19 1.401(10) . ? C19 C20 1.371(9) . ? C19 C23 1.439(11) . ? C20 C21 1.393(9) . ? C21 C22 1.411(9) . ? C21 C24 1.522(9) . ? C24 C25 1.519(10) . ? C25 C26 1.375(10) . ? C25 C30 1.416(9) . ? C26 C27 1.376(10) . ? C27 C28 1.400(9) . ? C28 C29 1.398(10) . ? C29 C30 1.387(10) . ? C29 C31 1.523(9) . ? C32 C33 1.487(10) . ? C34 C35 1.483(10) . ? C36 C37 1.366(9) . ? C37 C38 1.358(9) . ? C38 C39 1.395(9) . ? C39 C40 1.384(9) . ? C56 C61 1.380(17) . ? C56 C57 1.401(17) . ? C61 N60 1.312(16) . ? C54 C53 1.350(17) . ? C54 C55 1.431(17) . ? C53 C52 1.356(16) . ? C52 C51 1.314(16) . ? C51 C50 1.351(16) . ? C57 C58 1.372(17) . ? C55 C50 1.389(17) . ? N60 C59 1.297(17) . ? C59 C58 1.340(17) . ? C65 C66 1.399(18) . ? C65 C67 1.44(3) 2_657 ? C62 C64 1.28(3) 2_657 ? C62 C63 1.398(18) . ? C66 C67 1.403(19) . ? C63 C64 1.363(19) . ? C67 C65 1.44(3) 2_657 ? C64 C62 1.28(3) 2_657 ? C71 N70 1.287(15) . ? C71 C72 1.383(17) . ? C68 C73 1.373(16) . ? C68 C69 1.406(18) . ? C72 C73 1.404(16) . ? C69 N70 1.338(16) . ? 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 C36 N1 C40 116.7(6) . . ? C6 C1 C2 118.5(7) . . ? C6 C1 C31 120.1(6) . . ? C2 C1 C31 121.4(7) . . ? C1 C2 C3 121.5(6) . . ? C4 C3 C2 118.6(6) . . ? C4 C3 C7 120.4(7) . . ? C2 C3 C7 121.0(7) . . ? C3 C4 C5 122.1(7) . . ? C4 C5 C6 118.3(6) . . ? C4 C5 C8 121.1(6) . . ? C6 C5 C8 120.6(6) . . ? C14 O6 C32 111.2(5) . . ? O3 C6 C1 115.6(6) . . ? O3 C6 C5 123.4(6) . . ? C1 C6 C5 121.0(6) . . ? O1 C7 O2 117.2(9) . . ? O1 C7 C3 124.1(8) . . ? O2 C7 C3 118.6(8) . . ? C5 C8 C9 111.5(5) . . ? C14 C9 C10 118.5(6) . . ? C14 C9 C8 121.4(6) . . ? C10 C9 C8 120.1(6) . . ? C30 O10 C34 115.3(5) . . ? C11 C10 C9 121.0(6) . . ? C12 C11 C10 119.3(6) . . ? C12 C11 C15 123.1(6) . . ? C10 C11 C15 117.6(6) . . ? C11 C12 C13 122.1(6) . . ? C12 C13 C14 116.3(6) . . ? C12 C13 C16 121.0(6) . . ? C14 C13 C16 122.7(6) . . ? C9 C14 O6 119.5(6) . . ? C9 C14 C13 122.6(6) . . ? O6 C14 C13 117.8(6) . . ? O4 C15 O5 123.4(6) . . ? O4 C15 C11 122.3(6) . . ? O5 C15 C11 114.3(6) . . ? C13 C16 C17 113.1(5) . . ? C22 C17 C18 117.3(6) . . ? C22 C17 C16 121.4(6) . . ? C18 C17 C16 121.3(6) . . ? C17 C18 C19 121.5(6) . . ? C20 C19 C18 119.4(6) . . ? C20 C19 C23 118.9(7) . . ? C18 C19 C23 121.7(7) . . ? C19 C20 C21 121.8(6) . . ? C20 C21 C22 117.8(6) . . ? C20 C21 C24 121.0(6) . . ? C22 C21 C24 121.2(6) . . ? O9 C22 C17 115.7(6) . . ? O9 C22 C21 122.0(6) . . ? C17 C22 C21 122.3(6) . . ? O7 C23 O8 112.0(10) . . ? O7 C23 C19 122.4(11) . . ? O8 C23 C19 125.2(8) . . ? C25 C24 C21 112.1(6) . . ? C26 C25 C30 118.8(7) . . ? C26 C25 C24 120.6(6) . . ? C30 C25 C24 120.5(7) . . ? C25 C26 C27 121.5(7) . . ? C26 C27 C28 119.4(7) . . ? C29 C28 C27 120.8(7) . . ? C30 C29 C28 118.4(6) . . ? C30 C29 C31 121.6(7) . . ? C28 C29 C31 119.9(7) . . ? C29 C30 O10 120.0(6) . . ? C29 C30 C25 121.0(7) . . ? O10 C30 C25 118.9(7) . . ? C29 C31 C1 111.8(6) . . ? O6 C32 C33 108.9(6) . . ? O10 C34 C35 111.9(7) . . ? N1 C36 C37 123.9(6) . . ? C38 C37 C36 119.1(6) . . ? C37 C38 C39 119.4(6) . . ? C40 C39 C38 117.5(6) . . ? N1 C40 C39 123.5(6) . . ? C61 C56 C57 117.9(18) . . ? N60 C61 C56 121.8(19) . . ? C53 C54 C55 119.6(18) . . ? C54 C53 C52 122.1(18) . . ? C51 C52 C53 120.0(16) . . ? C52 C51 C50 120.5(16) . . ? C58 C57 C56 119.8(17) . . ? C50 C55 C54 114.7(18) . . ? C59 N60 C61 117.3(17) . . ? N60 C59 C58 128(2) . . ? C59 C58 C57 115.1(18) . . ? C66 C65 C67 121(2) . 2_657 ? C64 C62 C63 121(2) 2_657 . ? C65 C66 C67 125(3) . . ? C64 C63 C62 114(2) . . ? C66 C67 C65 114(2) . 2_657 ? C62 C64 C63 125(2) 2_657 . ? N70 C71 C72 129.6(15) . . ? C73 C68 C69 119.0(16) . . ? C71 C72 C73 117.3(14) . . ? N70 C69 C68 125.9(17) . . ? C68 C73 C72 116.2(14) . . ? C71 N70 C69 112.0(16) . . ? C51 C50 C55 123.2(18) . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 20.69 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.448 _refine_diff_density_min -0.523 _refine_diff_density_rms 0.068