# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 188/261 data_10 _audit_creation_method SHELXL-97 _journal_name_full ; Chemistry, A European Journal ; _publ_section_title ; A Closer Look at the Conformational Behaviour of Calix[4]arene Dicarboxylic Acids and their (Supramolecular) Interactions with Aliphatic Amines e.g. (-)-Ephedrine ; _publ_contact_author_name ; Mikkel J\/orgensen ; _publ_contact_author_address ; Condensed Matter Physics and Chemistry Department Ris\/o National Laboratory DK-4000 Roskilde Denmark ; _publ_contact_author_email 'mikkel.joergensen@risoe.dk' loop_ _publ_author_name _publ_author_address 'Krebs, Frederik C.' ; Department of Chemistry Technical University of Denmark DK-2800 Lyngby Denmark ; 'Sommer-Larsen, Peter' ; Condensed Matter Physics and Chemistry Department Ris\/o National Laboratory DK-4000 Roskilde Denmark ; 'J\/orgensen, Mikkel' ; Condensed Matter Physics and Chemistry Department Ris\/o National Laboratory DK-4000 Roskilde Denmark ; _chemical_name_systematic ; 5,17-Bis((E)-(2-phenyl-1-ethenyl)-11,23-dibromo- 25,26,27,28-tetrapropoxycalix[4]arene ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C56 H58 Br2 O4' _chemical_formula_weight 954.84 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' 'Br' 'Br' -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 25.7135(4) _cell_length_b 9.52320(10) _cell_length_c 19.8894(3) _cell_angle_alpha 90.00 _cell_angle_beta 105.57 _cell_angle_gamma 90.00 _cell_volume 4691.62(11) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.63 _exptl_crystal_size_mid 0.63 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.352 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1984 _exptl_absorpt_coefficient_mu 1.774 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details 'SADABS (Sheldrick)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Siemens SMART CCD' _diffrn_measurement_method 'omega scan, frame data integration' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 24364 _diffrn_reflns_av_R_equivalents 0.0406 _diffrn_reflns_av_sigmaI/netI 0.0308 _diffrn_reflns_limit_h_min -32 _diffrn_reflns_limit_h_max 32 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.64 _diffrn_reflns_theta_max 26.58 _reflns_number_total 4851 _reflns_number_gt 4165 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART Siemens' _computing_cell_refinement 'SAINT Siemens' _computing_data_reduction 'SAINT Siemens' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Sheldrick)' _computing_publication_material 'XCIF (Sheldrick)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0395P)^2^+3.4643P] 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 4851 _refine_ls_number_parameters 280 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0343 _refine_ls_R_factor_gt 0.0277 _refine_ls_wR_factor_ref 0.0749 _refine_ls_wR_factor_gt 0.0722 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _refine_ls_shift/su_max 0.015 _refine_ls_shift/su_mean 0.002 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 Br1 Br 0.070984(7) 0.343350(18) 0.204512(9) 0.02862(7) Uani 1 1 d . . . O1 O -0.04281(5) 0.94161(12) 0.16743(6) 0.0214(3) Uani 1 1 d . . . O2 O 0.08928(5) 0.97383(12) 0.18798(6) 0.0207(2) Uani 1 1 d . . . C1 C -0.14404(7) 0.83905(18) 0.18112(8) 0.0211(3) Uani 1 1 d . . . H1A H -0.1819 0.8134 0.1710 0.025 Uiso 1 1 calc . . . H1B H -0.1411 0.9394 0.1896 0.025 Uiso 1 1 calc . . . C2 C -0.12240(7) 0.80237(18) 0.11939(8) 0.0199(3) Uani 1 1 d . . . C3 C -0.15005(7) 0.70940(19) 0.06832(9) 0.0222(3) Uani 1 1 d . . . H3 H -0.1844 0.6796 0.0688 0.027 Uiso 1 1 calc . . . C4 C -0.12733(7) 0.65945(17) 0.01610(9) 0.0215(3) Uani 1 1 d . . . C5 C -0.07490(7) 0.70316(18) 0.01812(8) 0.0205(3) Uani 1 1 d . . . H5 H -0.0588 0.6689 -0.0153 0.025 Uiso 1 1 calc . . . C6 C -0.04600(7) 0.79631(18) 0.06848(8) 0.0190(3) Uani 1 1 d . . . C7 C -0.07135(7) 0.84945(17) 0.11726(8) 0.0185(3) Uani 1 1 d . . . C8 C 0.01251(7) 0.83134(17) 0.07481(8) 0.0193(3) Uani 1 1 d . . . H8A H 0.0178 0.9320 0.0798 0.023 Uiso 1 1 calc . . . H8B H 0.0219 0.8020 0.0328 0.023 Uiso 1 1 calc . . . C9 C 0.04881(6) 0.75729(17) 0.13783(8) 0.0180(3) Uani 1 1 d . . . C10 C 0.04525(7) 0.61188(18) 0.14237(8) 0.0196(3) Uani 1 1 d . . . H10 H 0.0228 0.5615 0.1059 0.023 Uiso 1 1 calc . . . C11 C 0.07516(6) 0.54256(18) 0.20110(8) 0.0200(3) Uani 1 1 d . . . C12 C 0.10749(7) 0.61464(19) 0.25747(8) 0.0201(3) Uani 1 1 d . . . H12 H 0.1262 0.5662 0.2972 0.024 Uiso 1 1 calc . . . C13 C 0.11189(6) 0.76036(18) 0.25429(8) 0.0187(3) Uani 1 1 d . . . C14 C 0.08393(7) 0.82970(17) 0.19302(8) 0.0180(3) Uani 1 1 d . . . C15 C -0.15543(7) 0.56230(19) -0.03899(9) 0.0244(4) Uani 1 1 d . . . H15 H -0.1383 0.5425 -0.0736 0.029 Uiso 1 1 calc . . . C16 C -0.20263(8) 0.4994(2) -0.04499(9) 0.0278(4) Uani 1 1 d . . . H16 H -0.2200 0.5185 -0.0106 0.033 Uiso 1 1 calc . . . C17 C -0.22988(7) 0.4022(2) -0.10103(9) 0.0261(4) Uani 1 1 d . . . C18 C -0.21315(8) 0.3843(2) -0.16167(10) 0.0306(4) Uani 1 1 d . . . H18 H -0.1837 0.4347 -0.1674 0.037 Uiso 1 1 calc . . . C19 C -0.23994(8) 0.2924(2) -0.21336(10) 0.0342(5) Uani 1 1 d . . . H19 H -0.2283 0.2821 -0.2535 0.041 Uiso 1 1 calc . . . C20 C -0.28355(8) 0.2160(2) -0.20595(11) 0.0349(5) Uani 1 1 d . . . H20 H -0.3013 0.1541 -0.2407 0.042 Uiso 1 1 calc . . . C21 C -0.30062(8) 0.2324(2) -0.14644(11) 0.0358(5) Uani 1 1 d . . . H21 H -0.3300 0.1810 -0.1410 0.043 Uiso 1 1 calc . . . C22 C -0.27435(8) 0.3249(2) -0.09459(10) 0.0313(4) Uani 1 1 d . . . H22 H -0.2866 0.3355 -0.0549 0.038 Uiso 1 1 calc . . . C23 C -0.06013(8) 1.0860(2) 0.15612(10) 0.0292(4) Uani 1 1 d . . . H23A H -0.0432 1.1398 0.1976 0.035 Uiso 1 1 calc . . . H23B H -0.0989 1.0900 0.1496 0.035 Uiso 1 1 calc . . . C24 C -0.04704(8) 1.15360(19) 0.09429(10) 0.0295(4) Uani 1 1 d . . . H24A H -0.0619 1.0971 0.0530 0.035 Uiso 1 1 calc . . . H24B H -0.0082 1.1570 0.1021 0.035 Uiso 1 1 calc . . . C25 C -0.07002(9) 1.3027(2) 0.08192(11) 0.0354(5) Uani 1 1 d . . . H25A H -0.0599 1.3440 0.0433 0.053 Uiso 1 1 calc . . . H25B H -0.0559 1.3583 0.1230 0.053 Uiso 1 1 calc . . . H25C H -0.1087 1.2990 0.0717 0.053 Uiso 1 1 calc . . . C26 C 0.13917(7) 1.01450(18) 0.17239(9) 0.0235(4) Uani 1 1 d . . . H26A H 0.1687 0.9606 0.2016 0.028 Uiso 1 1 calc . . . H26B H 0.1461 1.1129 0.1839 0.028 Uiso 1 1 calc . . . C27 C 0.13799(8) 0.9919(2) 0.09694(10) 0.0318(4) Uani 1 1 d . . . H27A H 0.1073 1.0412 0.0672 0.038 Uiso 1 1 calc . . . H27B H 0.1338 0.8926 0.0860 0.038 Uiso 1 1 calc . . . C28 C 0.19009(9) 1.0454(3) 0.08265(12) 0.0452(6) Uani 1 1 d . . . H28A H 0.1892 1.0272 0.0349 0.068 Uiso 1 1 calc . . . H28B H 0.2205 0.9981 0.1128 0.068 Uiso 1 1 calc . . . H28C H 0.1933 1.1447 0.0913 0.068 Uiso 1 1 calc . . . 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 Br1 0.02802(11) 0.01712(11) 0.03540(11) 0.00427(7) -0.00068(8) -0.00036(7) O1 0.0214(6) 0.0214(6) 0.0192(6) -0.0013(5) 0.0017(5) 0.0000(5) O2 0.0179(6) 0.0170(6) 0.0274(6) -0.0007(5) 0.0065(5) -0.0005(5) C1 0.0166(8) 0.0258(9) 0.0198(8) 0.0020(7) 0.0031(7) 0.0025(7) C2 0.0184(8) 0.0219(8) 0.0179(8) 0.0038(6) 0.0021(6) 0.0043(7) C3 0.0168(8) 0.0262(9) 0.0217(8) 0.0025(7) 0.0019(7) -0.0009(7) C4 0.0196(9) 0.0217(9) 0.0200(8) 0.0031(6) 0.0000(7) 0.0020(7) C5 0.0213(9) 0.0217(8) 0.0176(8) 0.0018(6) 0.0039(7) 0.0041(7) C6 0.0187(8) 0.0189(8) 0.0178(7) 0.0050(6) 0.0019(6) 0.0033(6) C7 0.0185(8) 0.0183(8) 0.0160(7) 0.0029(6) -0.0002(6) 0.0025(6) C8 0.0181(8) 0.0204(8) 0.0190(8) 0.0019(6) 0.0040(6) 0.0004(6) C9 0.0144(8) 0.0208(8) 0.0193(8) 0.0021(6) 0.0056(6) 0.0019(6) C10 0.0171(8) 0.0206(8) 0.0203(8) -0.0014(6) 0.0038(7) -0.0008(6) C11 0.0173(8) 0.0164(8) 0.0268(9) 0.0023(6) 0.0068(7) 0.0011(6) C12 0.0152(8) 0.0240(9) 0.0202(8) 0.0043(6) 0.0034(6) 0.0019(6) C13 0.0135(8) 0.0236(9) 0.0196(8) -0.0018(6) 0.0052(6) -0.0014(6) C14 0.0156(8) 0.0176(8) 0.0222(8) -0.0003(6) 0.0076(6) 0.0009(6) C15 0.0235(9) 0.0268(9) 0.0216(8) -0.0007(7) 0.0035(7) 0.0014(7) C16 0.0261(10) 0.0337(10) 0.0229(8) -0.0048(7) 0.0056(7) -0.0031(8) C17 0.0194(9) 0.0288(10) 0.0266(9) -0.0030(7) 0.0003(7) 0.0014(7) C18 0.0211(9) 0.0401(11) 0.0293(9) -0.0050(8) 0.0043(8) -0.0025(8) C19 0.0258(10) 0.0465(12) 0.0274(9) -0.0090(9) 0.0023(8) 0.0070(9) C20 0.0229(10) 0.0365(11) 0.0375(10) -0.0141(9) -0.0052(8) 0.0056(8) C21 0.0248(10) 0.0346(11) 0.0462(12) -0.0097(9) 0.0064(9) -0.0049(8) C22 0.0259(10) 0.0358(11) 0.0327(10) -0.0070(8) 0.0086(8) -0.0031(8) C23 0.0355(11) 0.0229(9) 0.0284(9) -0.0029(7) 0.0071(8) 0.0000(8) C24 0.0319(10) 0.0236(10) 0.0325(10) -0.0020(7) 0.0079(8) -0.0020(8) C25 0.0393(12) 0.0262(10) 0.0434(11) 0.0056(9) 0.0156(10) 0.0043(9) C26 0.0187(8) 0.0195(9) 0.0328(9) 0.0021(7) 0.0078(7) -0.0017(7) C27 0.0321(11) 0.0331(11) 0.0320(10) 0.0085(8) 0.0118(8) 0.0015(8) C28 0.0362(12) 0.0537(14) 0.0524(13) 0.0243(11) 0.0237(11) 0.0107(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C11 1.9024(17) . ? O1 C7 1.3825(19) . ? O1 C23 1.444(2) . ? O2 C14 1.3858(19) . ? O2 C26 1.451(2) . ? C1 C2 1.518(2) . ? C1 C13 1.525(2) 2 ? C2 C3 1.390(2) . ? C2 C7 1.398(2) . ? C3 C4 1.404(2) . ? C4 C5 1.401(2) . ? C4 C15 1.467(2) . ? C5 C6 1.394(2) . ? C6 C7 1.401(2) . ? C6 C8 1.513(2) . ? C8 C9 1.520(2) . ? C9 C10 1.392(2) . ? C9 C14 1.401(2) . ? C10 C11 1.382(2) . ? C11 C12 1.385(2) . ? C12 C13 1.395(2) . ? C13 C14 1.403(2) . ? C13 C1 1.525(2) 2 ? C15 C16 1.330(3) . ? C16 C17 1.473(2) . ? C17 C22 1.395(3) . ? C17 C18 1.396(3) . ? C18 C19 1.385(3) . ? C19 C20 1.377(3) . ? C20 C21 1.377(3) . ? C21 C22 1.386(3) . ? C23 C24 1.504(3) . ? C24 C25 1.532(3) . ? C26 C27 1.508(3) . ? C27 C28 1.530(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 C7 O1 C23 114.22(13) . . ? C14 O2 C26 112.98(12) . . ? C2 C1 C13 109.55(13) . 2 ? C3 C2 C7 118.83(15) . . ? C3 C2 C1 120.70(15) . . ? C7 C2 C1 120.09(15) . . ? C2 C3 C4 121.55(16) . . ? C5 C4 C3 117.80(15) . . ? C5 C4 C15 119.06(15) . . ? C3 C4 C15 123.13(16) . . ? C6 C5 C4 122.20(15) . . ? C5 C6 C7 118.05(15) . . ? C5 C6 C8 121.77(15) . . ? C7 C6 C8 120.00(15) . . ? O1 C7 C2 120.16(14) . . ? O1 C7 C6 118.28(15) . . ? C2 C7 C6 121.35(15) . . ? C6 C8 C9 110.07(13) . . ? C10 C9 C14 118.58(15) . . ? C10 C9 C8 118.57(14) . . ? C14 C9 C8 122.79(15) . . ? C11 C10 C9 119.91(15) . . ? C10 C11 C12 121.63(16) . . ? C10 C11 Br1 118.86(13) . . ? C12 C11 Br1 119.51(12) . . ? C11 C12 C13 119.64(15) . . ? C12 C13 C14 118.60(15) . . ? C12 C13 C1 118.87(14) . 2 ? C14 C13 C1 122.42(15) . 2 ? O2 C14 C9 119.10(14) . . ? O2 C14 C13 119.43(14) . . ? C9 C14 C13 121.41(15) . . ? C16 C15 C4 127.28(16) . . ? C15 C16 C17 126.04(17) . . ? C22 C17 C18 117.75(17) . . ? C22 C17 C16 119.82(16) . . ? C18 C17 C16 122.43(17) . . ? C19 C18 C17 120.77(18) . . ? C20 C19 C18 120.76(18) . . ? C19 C20 C21 119.25(18) . . ? C20 C21 C22 120.48(19) . . ? C21 C22 C17 120.99(18) . . ? O1 C23 C24 114.07(15) . . ? C23 C24 C25 111.52(16) . . ? O2 C26 C27 113.07(14) . . ? C26 C27 C28 110.66(17) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 26.58 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.347 _refine_diff_density_min -0.684 _refine_diff_density_rms 0.055 data_11(dabco)2 _audit_creation_method SHELXL-97 _journal_name_full ; Chemistry, A European Journal ; _publ_section_title ; A Closer Look at the Conformational Behaviour of Calix[4]arene Dicarboxylic Acids and their (Supramolecular) Interactions with Aliphatic Amines e.g. (-)-Ephedrine ; _publ_contact_author_name ; Mikkel J\/orgensen ; _publ_contact_author_address ; Condensed Matter Physics and Chemistry Department Ris\/o National Laboratory DK-4000 Roskilde Denmark ; _publ_contact_author_email 'mikkel.joergensen@risoe.dk' loop_ _publ_author_name _publ_author_address 'Krebs, Frederik C.' ; Department of Chemistry Technical University of Denmark DK-2800 Lyngby Denmark ; 'Sommer-Larsen, Peter' ; Condensed Matter Physics and Chemistry Department Ris\/o National Laboratory DK-4000 Roskilde Denmark ; 'J\/orgensen, Mikkel' ; Condensed Matter Physics and Chemistry Department Ris\/o National Laboratory DK-4000 Roskilde Denmark ; _chemical_name_systematic ; 11,23-bis((E)-(2-phenyl-1-ethenyl)- 25,26,27,28-tetrapropoxycalix[4]arene-5,17- dicarboxylic acid bis- 1,4-diaza[2,2,2]bicyclooctane salt ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C72 H87 N5 O8' _chemical_formula_weight 1150.47 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 13.062(3) _cell_length_b 13.325(3) _cell_length_c 20.365(4) _cell_angle_alpha 96.75(3) _cell_angle_beta 93.04(3) _cell_angle_gamma 110.93(3) _cell_volume 3270.4(11) _cell_formula_units_Z 2 _cell_measurement_temperature 120(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 0.35 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.168 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1236 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details 'SADABS (Sheldrick)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Siemens SMART CCD' _diffrn_measurement_method 'omega scan, frame data integration' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 34859 _diffrn_reflns_av_R_equivalents 0.3159 _diffrn_reflns_av_sigmaI/netI 0.5490 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.01 _diffrn_reflns_theta_max 26.37 _reflns_number_total 13338 _reflns_number_gt 2682 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART Siemens' _computing_cell_refinement 'SAINT Siemens' _computing_data_reduction 'SAINT Siemens' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Sheldrick)' _computing_publication_material 'XCIF (Sheldrick)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1893P)^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 13338 _refine_ls_number_parameters 735 _refine_ls_number_restraints 10 _refine_ls_R_factor_all 0.4304 _refine_ls_R_factor_gt 0.1352 _refine_ls_wR_factor_ref 0.4616 _refine_ls_wR_factor_gt 0.3159 _refine_ls_goodness_of_fit_ref 0.906 _refine_ls_restrained_S_all 0.906 _refine_ls_shift/su_max 0.466 _refine_ls_shift/su_mean 0.017 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 0.5969(6) 0.1664(6) 0.4576(3) 0.058(2) Uani 1 1 d . . . O2 O 0.4918(7) 0.1021(7) 0.3614(3) 0.057(2) Uani 1 1 d . . . O3 O 1.4764(7) -0.0321(6) 0.1588(3) 0.063(2) Uani 1 1 d . . . O4 O 1.3749(6) -0.0756(6) 0.0614(4) 0.059(2) Uani 1 1 d . . . O5 O 0.9433(6) 0.2154(6) 0.1009(3) 0.051(2) Uani 1 1 d . . . O6 O 0.9631(6) 0.2845(6) 0.2569(3) 0.052(2) Uani 1 1 d . . . O7 O 1.2177(6) 0.3717(6) 0.3551(3) 0.0458(19) Uani 1 1 d . . . O8 O 1.1661(6) 0.2410(6) 0.1971(3) 0.045(2) Uani 1 1 d . . . N1 N 1.3197(12) -0.1386(14) 0.2763(9) 0.164(7) Uani 1 1 d D . . N2 N 1.5954(9) -0.3095(9) -0.0073(5) 0.063(3) Uani 1 1 d . . . N3 N 1.4897(8) -0.1876(8) 0.0259(4) 0.054(3) Uani 1 1 d . . . H3B H 1.4527 -0.1431 0.0379 0.064 Uiso 1 1 calc R . . N4 N 0.4126(7) 0.1246(7) 0.5061(4) 0.048(2) Uani 1 1 d . . . H4A H 0.4751 0.1326 0.4860 0.058 Uiso 1 1 calc R . . N5 N 0.2384(8) 0.1035(8) 0.5636(4) 0.054(3) Uani 1 1 d . . . C1 C 1.0846(8) 0.0918(9) 0.0793(5) 0.047(3) Uani 1 1 d . . . H1AA H 1.0754 0.0399 0.0398 0.057 Uiso 1 1 calc . . . H1BA H 1.0949 0.1615 0.0653 0.057 Uiso 1 1 calc . . . C2 C 0.9785(9) 0.0552(9) 0.1149(5) 0.043(3) Uani 1 1 d . . . C3 C 0.9470(9) -0.0440(10) 0.1387(5) 0.057(3) Uani 1 1 d . . . H3A H 0.9890 -0.0870 0.1314 0.069 Uiso 1 1 calc . . . C4 C 0.8547(9) -0.0807(9) 0.1729(5) 0.053(3) Uani 1 1 d . . . C5 C 0.7956(9) -0.0115(12) 0.1844(5) 0.061(4) Uani 1 1 d . . . H5A H 0.7344 -0.0343 0.2081 0.074 Uiso 1 1 calc . . . C6 C 0.8228(9) 0.0867(10) 0.1629(5) 0.049(3) Uani 1 1 d . . . C7 C 0.9148(9) 0.1177(10) 0.1236(5) 0.047(3) Uani 1 1 d . . . C8 C 0.7626(9) 0.1613(10) 0.1797(5) 0.061(4) Uani 1 1 d . . . H8AA H 0.6856 0.1258 0.1625 0.073 Uiso 1 1 calc . . . H8BA H 0.7936 0.2263 0.1592 0.073 Uiso 1 1 calc . . . C9 C 0.7724(10) 0.1918(9) 0.2551(5) 0.045(3) Uani 1 1 d . . . C10 C 0.6779(9) 0.1579(9) 0.2893(5) 0.054(3) Uani 1 1 d . . . H10A H 0.6090 0.1217 0.2656 0.065 Uiso 1 1 calc . . . C11 C 0.6866(10) 0.1783(9) 0.3592(5) 0.046(3) Uani 1 1 d . . . C12 C 0.7906(9) 0.2263(8) 0.3930(5) 0.039(3) Uani 1 1 d . . . H12A H 0.7972 0.2371 0.4392 0.046 Uiso 1 1 calc . . . C13 C 0.8860(8) 0.2592(8) 0.3610(5) 0.037(3) Uani 1 1 d . . . C14 C 0.8721(9) 0.2485(9) 0.2918(5) 0.043(3) Uani 1 1 d . . . C15 C 0.9975(9) 0.2976(8) 0.3967(5) 0.042(3) Uani 1 1 d . . . H15A H 0.9915 0.3018 0.4441 0.050 Uiso 1 1 calc . . . H15B H 1.0390 0.3701 0.3876 0.050 Uiso 1 1 calc . . . C16 C 1.0599(8) 0.2227(9) 0.3765(4) 0.039(3) Uani 1 1 d . . . C17 C 1.0100(8) 0.1126(9) 0.3765(5) 0.040(3) Uani 1 1 d . . . H17A H 0.9393 0.0859 0.3896 0.048 Uiso 1 1 calc . . . C18 C 1.0612(8) 0.0392(7) 0.3577(4) 0.036(3) Uani 1 1 d . . . C19 C 1.1644(8) 0.0820(9) 0.3319(4) 0.038(3) Uani 1 1 d . . . H19A H 1.1980 0.0345 0.3157 0.045 Uiso 1 1 calc . . . C20 C 1.2152(7) 0.1883(8) 0.3300(4) 0.029(2) Uani 1 1 d . . . C21 C 1.1650(8) 0.2601(8) 0.3552(4) 0.035(3) Uani 1 1 d . . . C22 C 1.3205(8) 0.2290(8) 0.2959(5) 0.042(3) Uani 1 1 d . . . H22A H 1.3417 0.3062 0.2946 0.050 Uiso 1 1 calc . . . H22B H 1.3796 0.2176 0.3210 0.050 Uiso 1 1 calc . . . C23 C 1.3028(8) 0.1693(8) 0.2261(4) 0.031(2) Uani 1 1 d . . . C24 C 1.3601(8) 0.1018(9) 0.2075(5) 0.043(3) Uani 1 1 d . . . H24A H 1.4170 0.1004 0.2364 0.052 Uiso 1 1 calc . . . C25 C 1.3320(9) 0.0354(8) 0.1446(5) 0.040(3) Uani 1 1 d . . . C26 C 1.2455(9) 0.0330(8) 0.1053(5) 0.041(3) Uani 1 1 d . . . H26A H 1.2233 -0.0149 0.0657 0.049 Uiso 1 1 calc . . . C27 C 1.1870(8) 0.1017(9) 0.1225(5) 0.041(3) Uani 1 1 d . . . C28 C 1.2219(8) 0.1715(8) 0.1826(5) 0.030(2) Uani 1 1 d . . . C29 C 0.8190(12) -0.1920(12) 0.1912(7) 0.088(5) Uani 1 1 d . . . H29A H 0.8711 -0.2247 0.1889 0.106 Uiso 1 1 calc . . . C30 C 0.7224(13) -0.2515(15) 0.2106(7) 0.105(5) Uani 1 1 d . . . H30A H 0.6722 -0.2177 0.2190 0.125 Uiso 1 1 calc . . . C31 C 0.6893(13) -0.3671(10) 0.2196(9) 0.147(9) Uani 1 1 d G . . C32 C 0.7426(10) -0.4336(18) 0.1930(8) 0.190(11) Uani 1 1 d G . . H32 H 0.8014 -0.4060 0.1682 0.228 Uiso 1 1 calc . . . C33 C 0.7079(15) -0.5414(17) 0.2035(11) 0.44(4) Uani 1 1 d G . . H33 H 0.7436 -0.5859 0.1857 0.529 Uiso 1 1 calc . . . C34 C 0.6199(17) -0.5827(10) 0.2406(11) 0.30(2) Uani 1 1 d G . . H34 H 0.5968 -0.6549 0.2476 0.361 Uiso 1 1 calc . . . C35 C 0.5666(11) -0.5162(15) 0.2672(8) 0.229(16) Uani 1 1 d G . . H35 H 0.5078 -0.5439 0.2920 0.275 Uiso 1 1 calc . . . C36 C 0.6013(12) -0.4084(13) 0.2567(8) 0.185(10) Uani 1 1 d G . . H36 H 0.5656 -0.3639 0.2745 0.222 Uiso 1 1 calc . . . C37 C 1.0130 -0.0719 0.3644 0.042 Uani 1 1 d . . . H37A H 0.9371 -0.0980 0.3661 0.050 Uiso 1 1 calc . . . C38 C 1.0595(9) -0.1437(8) 0.3686(5) 0.047(3) Uani 1 1 d . . . H38A H 1.1339 -0.1221 0.3623 0.057 Uiso 1 1 calc . . . C39 C 1.0052(13) -0.2538(10) 0.3821(5) 0.062(4) Uani 1 1 d . . . C40 C 0.8916(14) -0.3125(11) 0.3644(8) 0.092(5) Uani 1 1 d . . . H40A H 0.8501 -0.2805 0.3423 0.110 Uiso 1 1 calc . . . C41 C 0.8406(17) -0.4162(13) 0.3792(11) 0.143(9) Uani 1 1 d . . . H41A H 0.7652 -0.4516 0.3678 0.171 Uiso 1 1 calc . . . C42 C 0.897(2) -0.4670(15) 0.4097(11) 0.138(11) Uani 1 1 d . . . H42A H 0.8615 -0.5372 0.4189 0.165 Uiso 1 1 calc . . . C43 C 1.009(2) -0.4139(15) 0.4273(7) 0.115(8) Uani 1 1 d . . . H43A H 1.0480 -0.4487 0.4491 0.138 Uiso 1 1 calc . . . C44 C 1.0667(13) -0.3063(12) 0.4126(6) 0.088(5) Uani 1 1 d . . . H44A H 1.1425 -0.2725 0.4230 0.106 Uiso 1 1 calc . . . C45 C 0.5843(10) 0.1463(10) 0.3932(6) 0.049(3) Uani 1 1 d . . . C46 C 1.4002(9) -0.0302(9) 0.1213(6) 0.043(3) Uani 1 1 d . . . C47 C 0.8906(10) 0.2046(11) 0.0351(6) 0.066(4) Uani 1 1 d . . . H47A H 0.8113 0.1702 0.0345 0.079 Uiso 1 1 calc . . . H47B H 0.9158 0.1600 0.0037 0.079 Uiso 1 1 calc . . . C48 C 0.9198(17) 0.3155(14) 0.0163(7) 0.139(8) Uani 1 1 d . . . H48A H 0.8875 0.3563 0.0455 0.166 Uiso 1 1 calc . . . H48B H 0.9992 0.3522 0.0235 0.166 Uiso 1 1 calc . . . C49 C 0.884(2) 0.3166(17) -0.0509(11) 0.216(12) Uani 1 1 d . . . H49A H 0.9025 0.3904 -0.0588 0.324 Uiso 1 1 calc . . . H49B H 0.8056 0.2792 -0.0589 0.324 Uiso 1 1 calc . . . H49C H 0.9196 0.2810 -0.0804 0.324 Uiso 1 1 calc . . . C50 C 1.0188(14) 0.4026(15) 0.2663(8) 0.104(5) Uani 1 1 d U . . H50A H 1.0071 0.4332 0.3096 0.125 Uiso 1 1 calc . . . H50B H 1.0974 0.4208 0.2648 0.125 Uiso 1 1 calc . . . C51 C 0.9805(14) 0.4446(18) 0.2194(9) 0.139(7) Uani 1 1 d . . . H51A H 0.9028 0.4293 0.2232 0.166 Uiso 1 1 calc . . . H51B H 0.9867 0.4086 0.1764 0.166 Uiso 1 1 calc . . . C52 C 1.0429(14) 0.5754(13) 0.2218(6) 0.100(5) Uani 1 1 d . . . H52A H 1.0118 0.5989 0.1856 0.151 Uiso 1 1 calc . . . H52B H 1.1200 0.5918 0.2182 0.151 Uiso 1 1 calc . . . H52C H 1.0337 0.6124 0.2632 0.151 Uiso 1 1 calc . . . C53 C 1.2900(12) 0.4250(11) 0.4138(8) 0.091(5) Uani 1 1 d D . . H53A H 1.3376 0.3858 0.4234 0.109 Uiso 1 1 calc . . . H53B H 1.2479 0.4279 0.4514 0.109 Uiso 1 1 calc . . . C54 C 1.361(3) 0.543(2) 0.402(2) 0.36(3) Uani 1 1 d . . . H54A H 1.4230 0.5774 0.4353 0.432 Uiso 1 1 calc . . . H54B H 1.3871 0.5431 0.3581 0.432 Uiso 1 1 calc . . . C55 C 1.274(3) 0.5999(17) 0.407(2) 0.50(4) Uani 1 1 d D . . H55A H 1.3103 0.6763 0.4066 0.753 Uiso 1 1 calc . . . H55B H 1.2414 0.5886 0.4483 0.753 Uiso 1 1 calc . . . H55C H 1.2179 0.5694 0.3706 0.753 Uiso 1 1 calc . . . C56 C 1.2049(14) 0.342(2) 0.1504(14) 0.191(15) Uani 1 1 d . . . H56A H 1.2309 0.3224 0.1090 0.229 Uiso 1 1 calc . . . H56B H 1.1484 0.3721 0.1422 0.229 Uiso 1 1 calc . . . C57 C 1.277(2) 0.399(2) 0.1908(8) 0.180(13) Uani 1 1 d . . . H57A H 1.3344 0.3701 0.1981 0.216 Uiso 1 1 calc . . . H57B H 1.2511 0.4171 0.2327 0.216 Uiso 1 1 calc . . . C58 C 1.3174(14) 0.5121(11) 0.1416(8) 0.118(6) Uani 1 1 d . . . H58A H 1.3842 0.5681 0.1627 0.177 Uiso 1 1 calc . . . H58B H 1.2600 0.5410 0.1388 0.177 Uiso 1 1 calc . . . H58C H 1.3291 0.4862 0.0977 0.177 Uiso 1 1 calc . . . C59 C 1.4664(12) -0.2368(15) 0.2576(9) 0.191(12) Uani 1 1 d D . . H59A H 1.5366 -0.1809 0.2554 0.287 Uiso 1 1 calc . . . H59B H 1.4447 -0.2855 0.2164 0.287 Uiso 1 1 calc . . . H59C H 1.4720 -0.2764 0.2932 0.287 Uiso 1 1 calc . . . C60 C 1.3820(15) -0.1863(16) 0.2699(10) 0.33(3) Uani 1 1 d D . . C61 C 1.5310(11) -0.2996(11) -0.0644(7) 0.079(4) Uani 1 1 d . . . H61A H 1.4829 -0.3716 -0.0854 0.095 Uiso 1 1 calc . . . H61B H 1.5803 -0.2666 -0.0964 0.095 Uiso 1 1 calc . . . C62 C 1.4602(10) -0.2305(10) -0.0462(5) 0.061(3) Uani 1 1 d . . . H62A H 1.4761 -0.1712 -0.0723 0.073 Uiso 1 1 calc . . . H62B H 1.3824 -0.2749 -0.0549 0.073 Uiso 1 1 calc . . . C63 C 1.5179(11) -0.3589(10) 0.0408(6) 0.080(4) Uani 1 1 d . . . H63A H 1.5581 -0.3705 0.0788 0.096 Uiso 1 1 calc . . . H63B H 1.4647 -0.4287 0.0200 0.096 Uiso 1 1 calc . . . C64 C 1.4561(10) -0.2800(9) 0.0644(6) 0.064(4) Uani 1 1 d . . . H64A H 1.3770 -0.3185 0.0568 0.077 Uiso 1 1 calc . . . H64B H 1.4756 -0.2535 0.1116 0.077 Uiso 1 1 calc . . . C65 C 1.6696(11) -0.2055(13) 0.0235(6) 0.069(4) Uani 1 1 d . . . H65A H 1.7248 -0.1752 -0.0061 0.083 Uiso 1 1 calc . . . H65B H 1.7071 -0.2132 0.0640 0.083 Uiso 1 1 calc . . . C66 C 1.6080(11) -0.1266(10) 0.0406(5) 0.057(3) Uani 1 1 d . . . H66A H 1.6251 -0.0958 0.0872 0.068 Uiso 1 1 calc . . . H66B H 1.6310 -0.0676 0.0143 0.068 Uiso 1 1 calc . . . C67 C 0.4356(9) 0.1265(9) 0.5788(5) 0.057(3) Uani 1 1 d . . . H67A H 0.4923 0.1951 0.5981 0.069 Uiso 1 1 calc . . . H67B H 0.4611 0.0684 0.5865 0.069 Uiso 1 1 calc . . . C68 C 0.3284(11) 0.1114(11) 0.6107(6) 0.073(4) Uani 1 1 d . . . H68A H 0.3079 0.0460 0.6314 0.088 Uiso 1 1 calc . . . H68B H 0.3409 0.1724 0.6453 0.088 Uiso 1 1 calc . . . C69 C 0.3753(9) 0.2186(10) 0.4958(5) 0.063(3) Uani 1 1 d . . . H69A H 0.3582 0.2181 0.4488 0.075 Uiso 1 1 calc . . . H69B H 0.4332 0.2874 0.5135 0.075 Uiso 1 1 calc . . . C70 C 0.2716(11) 0.2029(11) 0.5327(6) 0.076(4) Uani 1 1 d . . . H70A H 0.2863 0.2650 0.5668 0.092 Uiso 1 1 calc . . . H70B H 0.2114 0.1999 0.5016 0.092 Uiso 1 1 calc . . . C71 C 0.3264(9) 0.0215(9) 0.4774(5) 0.047(3) Uiso 1 1 d . . . H71A H 0.3498 -0.0384 0.4838 0.056 Uiso 1 1 calc . . . H71B H 0.3111 0.0200 0.4301 0.056 Uiso 1 1 calc . . . C72 C 0.2201(9) 0.0109(10) 0.5137(6) 0.058(3) Uiso 1 1 d . . . H72A H 0.1601 0.0041 0.4811 0.069 Uiso 1 1 calc . . . H72B H 0.1985 -0.0545 0.5345 0.069 Uiso 1 1 calc . . . 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 0.057(5) 0.089(6) 0.044(5) 0.024(4) 0.032(4) 0.036(5) O2 0.055(6) 0.094(7) 0.033(4) 0.022(4) 0.024(4) 0.035(5) O3 0.071(6) 0.099(7) 0.044(5) 0.018(4) 0.023(4) 0.059(6) O4 0.077(6) 0.063(6) 0.052(5) 0.007(4) 0.023(4) 0.043(5) O5 0.054(5) 0.075(6) 0.034(4) 0.009(4) 0.015(4) 0.035(5) O6 0.048(5) 0.063(6) 0.045(4) 0.000(4) 0.036(4) 0.018(4) O7 0.050(5) 0.049(5) 0.036(4) 0.004(4) 0.024(4) 0.013(4) O8 0.061(5) 0.049(5) 0.039(4) 0.023(4) 0.036(4) 0.028(4) N1 0.186(17) 0.196(17) 0.193(16) 0.075(14) 0.103(14) 0.144(15) N2 0.080(8) 0.075(8) 0.062(7) 0.031(6) 0.054(6) 0.048(7) N3 0.075(8) 0.068(7) 0.045(6) 0.026(5) 0.037(5) 0.049(6) N4 0.055(6) 0.082(7) 0.022(5) 0.021(5) 0.028(4) 0.035(6) N5 0.060(7) 0.075(7) 0.043(6) 0.016(5) 0.032(5) 0.036(6) C1 0.045(7) 0.073(9) 0.030(6) 0.000(6) 0.028(5) 0.027(7) C2 0.043(7) 0.061(8) 0.026(6) -0.005(6) 0.005(5) 0.024(7) C3 0.052(8) 0.070(9) 0.052(7) -0.007(7) 0.025(6) 0.026(7) C4 0.045(8) 0.055(9) 0.061(8) 0.013(6) 0.022(6) 0.016(7) C5 0.049(8) 0.102(11) 0.041(7) 0.011(7) 0.020(6) 0.034(8) C6 0.042(8) 0.070(9) 0.047(7) 0.001(7) 0.012(6) 0.035(7) C7 0.049(8) 0.071(9) 0.037(6) 0.003(6) 0.013(6) 0.042(7) C8 0.056(8) 0.112(11) 0.041(7) 0.018(7) 0.022(6) 0.057(8) C9 0.055(8) 0.070(8) 0.031(6) 0.017(6) 0.028(6) 0.040(7) C10 0.056(8) 0.077(9) 0.044(7) 0.022(6) 0.015(6) 0.038(7) C11 0.054(8) 0.061(8) 0.046(7) 0.021(6) 0.039(6) 0.039(7) C12 0.033(7) 0.047(7) 0.038(6) 0.004(5) 0.022(5) 0.016(6) C13 0.034(7) 0.043(7) 0.039(7) 0.002(5) 0.016(5) 0.018(6) C14 0.034(7) 0.056(8) 0.037(7) 0.006(6) 0.024(6) 0.012(6) C15 0.064(8) 0.033(6) 0.041(6) 0.010(5) 0.041(6) 0.027(6) C16 0.047(7) 0.045(8) 0.030(6) 0.001(5) 0.025(5) 0.021(6) C17 0.043(7) 0.052(8) 0.035(6) 0.007(6) 0.024(5) 0.025(7) C18 0.044(7) 0.026(6) 0.042(6) 0.019(5) 0.032(5) 0.009(5) C19 0.039(7) 0.058(8) 0.026(6) 0.012(5) 0.014(5) 0.025(6) C20 0.029(6) 0.032(7) 0.033(6) 0.012(5) 0.020(5) 0.015(5) C21 0.047(7) 0.028(7) 0.035(6) 0.010(5) 0.018(5) 0.015(6) C22 0.044(7) 0.046(7) 0.042(6) 0.015(5) 0.030(5) 0.018(6) C23 0.032(6) 0.047(7) 0.020(5) 0.003(5) 0.014(5) 0.022(6) C24 0.028(6) 0.061(8) 0.047(7) 0.032(6) 0.024(5) 0.013(6) C25 0.053(8) 0.051(7) 0.032(6) 0.014(6) 0.024(6) 0.034(7) C26 0.050(7) 0.058(8) 0.028(6) 0.012(5) 0.028(5) 0.030(7) C27 0.033(7) 0.062(8) 0.031(6) 0.018(6) 0.017(5) 0.016(6) C28 0.030(6) 0.034(6) 0.029(6) 0.006(5) 0.024(5) 0.012(5) C29 0.080(11) 0.079(11) 0.123(12) 0.033(9) 0.067(10) 0.037(9) C30 0.075(12) 0.127(16) 0.098(12) -0.005(11) 0.014(9) 0.028(12) C31 0.081(15) 0.065(13) 0.25(3) 0.063(16) 0.010(15) -0.033(12) C32 0.102(17) 0.075(16) 0.36(3) -0.014(19) -0.015(19) 0.018(14) C33 0.07(2) 0.11(2) 1.05(11) -0.02(4) -0.20(4) -0.010(17) C34 0.12(3) 0.098(19) 0.63(7) 0.01(3) -0.15(3) 0.024(19) C35 0.044(12) 0.15(2) 0.48(5) 0.17(3) -0.009(19) -0.025(14) C36 0.105(18) 0.097(17) 0.31(3) 0.048(19) 0.011(19) -0.015(13) C37 0.045 0.048 0.037 0.010 0.036 0.018 C38 0.074(8) 0.030(7) 0.050(7) 0.015(5) 0.047(6) 0.025(6) C39 0.112(12) 0.059(9) 0.031(7) 0.008(6) 0.043(7) 0.042(10) C40 0.091(12) 0.036(9) 0.148(14) -0.004(9) 0.068(10) 0.021(9) C41 0.17(2) 0.035(11) 0.24(2) 0.025(12) 0.151(18) 0.035(12) C42 0.23(3) 0.043(13) 0.133(18) 0.002(11) 0.134(19) 0.024(15) C43 0.28(3) 0.062(13) 0.042(9) 0.020(9) 0.078(13) 0.095(15) C44 0.172(16) 0.090(12) 0.029(7) 0.018(7) 0.040(8) 0.073(12) C45 0.039(8) 0.087(10) 0.040(7) 0.029(7) 0.026(6) 0.036(8) C46 0.037(7) 0.066(9) 0.043(7) 0.028(7) 0.024(6) 0.030(7) C47 0.066(9) 0.097(11) 0.045(8) 0.013(7) 0.014(6) 0.041(8) C48 0.23(2) 0.118(15) 0.058(10) 0.031(10) -0.040(12) 0.056(15) C49 0.29(3) 0.146(19) 0.15(2) 0.078(16) -0.04(2) 0.005(19) C50 0.104(5) 0.104(5) 0.103(5) 0.0149(13) 0.0116(11) 0.038(2) C51 0.106(14) 0.21(2) 0.160(17) 0.043(16) 0.077(12) 0.113(16) C52 0.161(16) 0.094(12) 0.063(9) 0.025(9) 0.049(9) 0.058(12) C53 0.101(12) 0.035(9) 0.107(12) -0.013(8) 0.008(10) -0.004(9) C54 0.32(4) 0.14(2) 0.56(6) -0.19(3) -0.33(5) 0.13(3) C55 0.37(6) 0.42(7) 0.43(6) -0.08(5) 0.28(5) -0.19(5) C56 0.054(12) 0.20(3) 0.28(3) -0.15(2) -0.035(16) 0.066(15) C57 0.40(4) 0.25(3) 0.062(11) 0.085(15) 0.118(17) 0.28(3) C58 0.175(17) 0.076(11) 0.123(13) 0.049(10) 0.113(12) 0.045(11) C59 0.20(3) 0.19(2) 0.086(14) 0.036(15) -0.045(15) -0.040(19) C60 0.30(4) 0.52(6) 0.17(2) -0.21(3) -0.13(3) 0.25(4) C61 0.090(11) 0.088(11) 0.072(9) 0.000(8) 0.059(8) 0.044(9) C62 0.074(9) 0.079(9) 0.042(7) 0.000(6) 0.024(6) 0.043(8) C63 0.119(12) 0.065(9) 0.088(9) 0.045(8) 0.083(9) 0.052(9) C64 0.088(10) 0.061(8) 0.071(8) 0.030(7) 0.060(7) 0.047(8) C65 0.068(10) 0.100(12) 0.061(8) 0.033(8) 0.030(7) 0.047(10) C66 0.068(10) 0.069(9) 0.039(7) 0.015(6) 0.017(6) 0.027(8) C67 0.060(8) 0.085(9) 0.039(7) 0.024(6) 0.026(6) 0.034(7) C68 0.080(10) 0.115(12) 0.042(7) 0.023(7) 0.040(7) 0.048(9) C69 0.063(9) 0.089(10) 0.050(7) 0.018(7) 0.027(6) 0.040(8) C70 0.106(11) 0.086(10) 0.075(9) 0.037(8) 0.058(8) 0.065(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 O1 C45 1.296(12) . ? O2 C45 1.243(12) . ? O3 C46 1.232(11) . ? O4 C46 1.266(12) . ? O5 C7 1.364(12) . ? O5 C47 1.442(12) . ? O6 C14 1.382(11) . ? O6 C50 1.462(17) . ? O7 C21 1.398(11) . ? O7 C53 1.424(15) . ? O8 C28 1.385(10) . ? O8 C56 1.69(3) . ? N1 C60 1.2009(10) . ? N2 C65 1.424(15) . ? N2 C61 1.445(15) . ? N2 C63 1.482(13) . ? N3 C66 1.461(13) . ? N3 C64 1.483(12) . ? N3 C62 1.489(13) . ? N4 C71 1.460(12) . ? N4 C67 1.492(11) . ? N4 C69 1.529(13) . ? N5 C72 1.442(13) . ? N5 C68 1.443(14) . ? N5 C70 1.466(13) . ? C1 C27 1.518(13) . ? C1 C2 1.545(13) . ? C2 C7 1.376(13) . ? C2 C3 1.391(14) . ? C3 C4 1.388(14) . ? C4 C5 1.406(15) . ? C4 C29 1.486(16) . ? C5 C6 1.361(15) . ? C6 C7 1.443(14) . ? C6 C8 1.492(14) . ? C8 C9 1.529(14) . ? C9 C14 1.374(14) . ? C9 C10 1.407(13) . ? C10 C11 1.407(13) . ? C11 C12 1.380(14) . ? C11 C45 1.486(13) . ? C12 C13 1.391(12) . ? C13 C14 1.395(13) . ? C13 C15 1.476(14) . ? C15 C16 1.533(12) . ? C16 C17 1.376(13) . ? C16 C21 1.395(12) . ? C17 C18 1.399(12) . ? C18 C37 1.413(9) . ? C18 C19 1.421(12) . ? C19 C20 1.339(12) . ? C20 C21 1.407(12) . ? C20 C22 1.524(12) . ? C22 C23 1.508(12) . ? C23 C28 1.353(12) . ? C23 C24 1.394(12) . ? C24 C25 1.418(14) . ? C25 C26 1.339(13) . ? C25 C46 1.512(13) . ? C26 C27 1.413(13) . ? C27 C28 1.393(13) . ? C29 C30 1.337(18) . ? C30 C31 1.481(19) . ? C31 C32 1.3900 . ? C31 C36 1.3900 . ? C32 C33 1.3900 . ? C33 C34 1.3900 . ? C34 C35 1.3900 . ? C35 C36 1.3900 . ? C37 C38 1.312(10) . ? C38 C39 1.450(15) . ? C39 C44 1.405(16) . ? C39 C40 1.410(17) . ? C40 C41 1.38(2) . ? C41 C42 1.34(3) . ? C42 C43 1.38(3) . ? C43 C44 1.44(2) . ? C47 C48 1.490(18) . ? C48 C49 1.43(2) . ? C50 C51 1.323(19) . ? C51 C52 1.63(2) . ? C53 C54 1.57(4) . ? C54 C55 1.57(3) . ? C56 C57 1.18(3) . ? C57 C58 1.84(2) . ? C59 C60 1.5012(11) . ? C61 C62 1.551(15) . ? C63 C64 1.587(14) . ? C65 C66 1.556(15) . ? C67 C68 1.533(14) . ? C69 C70 1.545(15) . ? C71 C72 1.577(14) . ? 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 C7 O5 C47 111.5(9) . . ? C14 O6 C50 114.1(9) . . ? C21 O7 C53 112.9(8) . . ? C28 O8 C56 109.9(8) . . ? C65 N2 C61 110.6(10) . . ? C65 N2 C63 108.7(10) . . ? C61 N2 C63 107.7(10) . . ? C66 N3 C64 109.6(9) . . ? C66 N3 C62 111.1(8) . . ? C64 N3 C62 108.9(9) . . ? C71 N4 C67 109.9(8) . . ? C71 N4 C69 109.9(8) . . ? C67 N4 C69 108.7(8) . . ? C72 N5 C68 107.7(9) . . ? C72 N5 C70 109.7(9) . . ? C68 N5 C70 107.9(10) . . ? C27 C1 C2 113.4(8) . . ? C7 C2 C3 119.3(10) . . ? C7 C2 C1 122.0(10) . . ? C3 C2 C1 118.7(9) . . ? C4 C3 C2 122.0(10) . . ? C3 C4 C5 117.0(11) . . ? C3 C4 C29 119.4(11) . . ? C5 C4 C29 123.5(11) . . ? C6 C5 C4 123.7(10) . . ? C5 C6 C7 117.0(10) . . ? C5 C6 C8 122.4(10) . . ? C7 C6 C8 120.6(11) . . ? O5 C7 C2 120.8(10) . . ? O5 C7 C6 118.3(9) . . ? C2 C7 C6 120.6(11) . . ? C6 C8 C9 109.5(8) . . ? C14 C9 C10 118.0(9) . . ? C14 C9 C8 122.0(9) . . ? C10 C9 C8 120.0(11) . . ? C9 C10 C11 120.6(10) . . ? C12 C11 C10 118.1(9) . . ? C12 C11 C45 123.0(10) . . ? C10 C11 C45 118.9(11) . . ? C11 C12 C13 122.9(9) . . ? C12 C13 C14 116.7(10) . . ? C12 C13 C15 122.8(9) . . ? C14 C13 C15 120.4(8) . . ? C9 C14 O6 116.9(9) . . ? C9 C14 C13 122.8(9) . . ? O6 C14 C13 119.8(10) . . ? C13 C15 C16 112.3(9) . . ? C17 C16 C21 117.3(9) . . ? C17 C16 C15 119.6(9) . . ? C21 C16 C15 123.1(9) . . ? C16 C17 C18 122.8(9) . . ? C17 C18 C37 121.8(8) . . ? C17 C18 C19 116.6(9) . . ? C37 C18 C19 121.6(8) . . ? C20 C19 C18 122.4(9) . . ? C19 C20 C21 118.7(9) . . ? C19 C20 C22 120.3(8) . . ? C21 C20 C22 120.9(8) . . ? C16 C21 O7 118.4(8) . . ? C16 C21 C20 121.8(9) . . ? O7 C21 C20 119.7(8) . . ? C23 C22 C20 110.2(8) . . ? C28 C23 C24 118.7(9) . . ? C28 C23 C22 119.8(8) . . ? C24 C23 C22 121.1(9) . . ? C23 C24 C25 120.2(9) . . ? C26 C25 C24 119.2(9) . . ? C26 C25 C46 120.2(10) . . ? C24 C25 C46 120.6(10) . . ? C25 C26 C27 121.6(9) . . ? C28 C27 C26 117.5(9) . . ? C28 C27 C1 122.0(9) . . ? C26 C27 C1 120.3(9) . . ? C23 C28 O8 121.2(8) . . ? C23 C28 C27 122.3(9) . . ? O8 C28 C27 116.4(9) . . ? C30 C29 C4 128.9(13) . . ? C29 C30 C31 124.9(15) . . ? C32 C31 C36 120.0 . . ? C32 C31 C30 122.7(16) . . ? C36 C31 C30 117.3(16) . . ? C33 C32 C31 120.0 . . ? C32 C33 C34 120.0 . . ? C33 C34 C35 120.0 . . ? C36 C35 C34 120.0 . . ? C35 C36 C31 120.0 . . ? C38 C37 C18 129.6(6) . . ? C37 C38 C39 125.7(10) . . ? C44 C39 C40 117.7(13) . . ? C44 C39 C38 119.8(14) . . ? C40 C39 C38 122.4(13) . . ? C41 C40 C39 121.7(16) . . ? C42 C41 C40 122(2) . . ? C41 C42 C43 119.2(19) . . ? C42 C43 C44 121.7(19) . . ? C39 C44 C43 118.0(16) . . ? O2 C45 O1 122.1(9) . . ? O2 C45 C11 121.5(10) . . ? O1 C45 C11 116.5(11) . . ? O3 C46 O4 125.5(10) . . ? O3 C46 C25 120.0(11) . . ? O4 C46 C25 114.5(10) . . ? O5 C47 C48 107.9(11) . . ? C49 C48 C47 114.1(15) . . ? C51 C50 O6 110.5(16) . . ? C50 C51 C52 114.8(18) . . ? O7 C53 C54 107.7(15) . . ? C55 C54 C53 101(3) . . ? C57 C56 O8 93(3) . . ? C56 C57 C58 93(2) . . ? N1 C60 C59 173.9(14) . . ? N2 C61 C62 112.8(9) . . ? N3 C62 C61 106.5(9) . . ? N2 C63 C64 109.1(8) . . ? N3 C64 C63 108.2(8) . . ? N2 C65 C66 111.3(10) . . ? N3 C66 C65 108.4(10) . . ? N4 C67 C68 107.9(9) . . ? N5 C68 C67 112.9(9) . . ? N4 C69 C70 107.2(9) . . ? N5 C70 C69 112.3(9) . . ? N4 C71 C72 107.6(8) . . ? N5 C72 C71 111.8(9) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.023 _refine_diff_density_min -0.568 _refine_diff_density_rms 0.098 data_2(dabco) _audit_creation_method SHELXL-97 _journal_name_full ; Chemistry, A European Journal ; _publ_section_title ; A Closer Look at the Conformational Behaviour of Calix[4]arene Dicarboxylic Acids and their (Supramolecular) Interactions with Aliphatic Amines e.g. (-)-Ephedrine ; _publ_contact_author_name ; Mikkel J\/orgensen ; _publ_contact_author_address ; Condensed Matter Physics and Chemistry Department Ris\/o National Laboratory DK-4000 Roskilde Denmark ; _publ_contact_author_email 'mikkel.joergensen@risoe.dk' loop_ _publ_author_name _publ_author_address 'Krebs, Frederik C.' ; Department of Chemistry Technical University of Denmark DK-2800 Lyngby Denmark ; 'Sommer-Larsen, Peter' ; Condensed Matter Physics and Chemistry Department Ris\/o National Laboratory DK-4000 Roskilde Denmark ; 'J\/orgensen, Mikkel' ; Condensed Matter Physics and Chemistry Department Ris\/o National Laboratory DK-4000 Roskilde Denmark ; _chemical_name_systematic ; 25,26,27,28-tetrapropoxy- calix[4]arene-5,17-dicarboxylic acid 1,4-diaza[2,2,2]bicyclooctane salt ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C54 H69 N5 O8' _chemical_formula_weight 916.14 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 10.754(2) _cell_length_b 12.014(2) _cell_length_c 21.851(4) _cell_angle_alpha 100.97(3) _cell_angle_beta 96.83(3) _cell_angle_gamma 110.11(3) _cell_volume 2550.0(9) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.193 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 984 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details 'SADABS (Sheldrick)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Siemens SMART CCD' _diffrn_measurement_method 'omega scan, frame data integration' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 26915 _diffrn_reflns_av_R_equivalents 0.1407 _diffrn_reflns_av_sigmaI/netI 0.2136 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 0.97 _diffrn_reflns_theta_max 26.37 _reflns_number_total 10373 _reflns_number_gt 4086 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART Siemens' _computing_cell_refinement 'SAINT Siemens' _computing_data_reduction 'SAINT Siemens' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Sheldrick)' _computing_publication_material 'XCIF (Sheldrick)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0798P)^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 10373 _refine_ls_number_parameters 640 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.2264 _refine_ls_R_factor_gt 0.0796 _refine_ls_wR_factor_ref 0.2110 _refine_ls_wR_factor_gt 0.1507 _refine_ls_goodness_of_fit_ref 0.963 _refine_ls_restrained_S_all 1.001 _refine_ls_shift/su_max 3.797 _refine_ls_shift/su_mean 0.029 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 0.0235(3) 0.3630(3) 0.29109(14) 0.0288(8) Uani 1 1 d . . . O2 O 0.0188(3) 0.1914(3) 0.38241(14) 0.0279(8) Uani 1 1 d . . . O3 O 0.2783(3) 0.1015(3) 0.38023(14) 0.0271(8) Uani 1 1 d . . . O4 O 0.2433(3) 0.2301(3) 0.26776(14) 0.0282(8) Uani 1 1 d . . . O5 O -0.3507(3) -0.0505(3) 0.04732(15) 0.0282(8) Uani 1 1 d . . . N1 N -0.5425(4) -0.2319(3) -0.02869(18) 0.0236(10) Uani 1 1 d . . . N2 N -0.7325(4) -0.4216(3) -0.09969(18) 0.0243(10) Uani 1 1 d . . . N3 N -0.3588(5) -0.4889(5) -0.1038(3) 0.0670(17) Uani 1 1 d . . . N4 N -0.6340(6) -0.2769(6) 0.2574(3) 0.093(2) Uani 1 1 d . . . N5 N -0.0253(5) -0.3079(5) 0.0179(2) 0.0519(14) Uani 1 1 d . . . O6 O -0.4759(3) -0.1063(3) 0.11958(15) 0.0349(9) Uani 1 1 d . . . O7 O -0.2144(4) -0.3935(3) 0.23462(17) 0.0446(11) Uani 1 1 d . . . O8 O -0.0757(3) -0.3795(3) 0.16508(15) 0.0300(9) Uani 1 1 d . . . C1 C 0.0981(5) 0.2850(4) 0.1687(2) 0.0270(12) Uani 1 1 d . A . H1A H 0.0858 0.3148 0.1311 0.032 Uiso 1 1 calc . . . H1B H 0.1552 0.3543 0.2034 0.032 Uiso 1 1 calc . . . C2 C -0.0391(5) 0.2255(4) 0.1859(2) 0.0255(12) Uani 1 1 d . . . C3 C -0.1401(5) 0.1285(4) 0.1403(2) 0.0215(11) Uani 1 1 d . . . H3 H -0.1244 0.1066 0.0996 0.026 Uiso 1 1 calc . . . C4 C -0.2641(5) 0.0637(4) 0.1547(2) 0.0210(11) Uani 1 1 d . . . C5 C -0.2870(5) 0.0957(4) 0.2157(2) 0.0228(11) Uani 1 1 d . . . H5 H -0.3683 0.0515 0.2258 0.027 Uiso 1 1 calc . . . C6 C -0.1899(5) 0.1929(4) 0.2620(2) 0.0241(12) Uani 1 1 d . . . C7 C -0.0691(5) 0.2602(4) 0.2456(2) 0.0236(12) Uani 1 1 d . . . C8 C -0.2181(5) 0.2188(5) 0.3287(2) 0.0317(13) Uani 1 1 d . . . H8A H -0.1477 0.2938 0.3546 0.038 Uiso 1 1 calc . . . H8B H -0.3036 0.2298 0.3268 0.038 Uiso 1 1 calc . . . C9 C -0.2234(5) 0.1142(4) 0.3588(2) 0.0272(12) Uani 1 1 d . . . C10 C -0.3465(5) 0.0211(5) 0.3586(2) 0.0348(14) Uani 1 1 d . . . H10 H -0.4275 0.0260 0.3417 0.042 Uiso 1 1 calc . . . C11 C -0.3489(5) -0.0763(5) 0.3828(2) 0.0370(14) Uani 1 1 d . . . H11 H -0.4314 -0.1357 0.3831 0.044 Uiso 1 1 calc . . . C12 C -0.2300(5) -0.0873(4) 0.4068(2) 0.0316(13) Uani 1 1 d . . . H12 H -0.2330 -0.1539 0.4234 0.038 Uiso 1 1 calc . . . C13 C -0.1047(5) 0.0013(4) 0.4064(2) 0.0263(12) Uani 1 1 d . . . C14 C -0.1057(5) 0.1027(4) 0.3841(2) 0.0263(12) Uani 1 1 d . . . C15 C 0.0267(5) -0.0181(4) 0.4214(2) 0.0265(12) Uani 1 1 d . . . H15A H 0.0166 -0.0762 0.4475 0.032 Uiso 1 1 calc . . . H15B H 0.0983 0.0586 0.4446 0.032 Uiso 1 1 calc . . . C16 C 0.0620(5) -0.0667(4) 0.3590(2) 0.0240(12) Uani 1 1 d . . . C17 C -0.0302(5) -0.1749(4) 0.3182(2) 0.0240(12) Uani 1 1 d . . . H17 H -0.1089 -0.2177 0.3308 0.029 Uiso 1 1 calc . . . C18 C -0.0074(5) -0.2207(4) 0.2589(2) 0.0223(11) Uani 1 1 d . . . C19 C 0.1091(5) -0.1544(4) 0.2396(2) 0.0222(11) Uani 1 1 d . . . H19 H 0.1235 -0.1837 0.1996 0.027 Uiso 1 1 calc . . . C20 C 0.2044(4) -0.0454(4) 0.2788(2) 0.0220(11) Uani 1 1 d . . . C21 C 0.1812(5) -0.0049(4) 0.3391(2) 0.0211(11) Uani 1 1 d . . . C22 C 0.3252(4) 0.0273(4) 0.2534(2) 0.0234(11) Uani 1 1 d . A . H22A H 0.3852 0.0976 0.2868 0.028 Uiso 1 1 calc . . . H22B H 0.3752 -0.0236 0.2403 0.028 Uiso 1 1 calc . . . C23 C 0.2774(4) 0.0695(4) 0.1975(2) 0.0246(12) Uani 1 1 d . . . C24 C 0.2661(5) 0.0061(4) 0.1349(2) 0.0261(12) Uani 1 1 d . A . H24 H 0.2990 -0.0565 0.1276 0.031 Uiso 1 1 calc . . . C25 C 0.2067(5) 0.0357(5) 0.0842(2) 0.0306(13) Uani 1 1 d . . . H25 H 0.2004 -0.0062 0.0428 0.037 Uiso 1 1 calc . . . C26 C 0.1562(5) 0.1282(4) 0.0949(2) 0.0280(12) Uani 1 1 d . A . H26 H 0.1149 0.1465 0.0604 0.034 Uiso 1 1 calc . . . C27 C 0.1662(4) 0.1938(4) 0.1563(2) 0.0222(11) Uani 1 1 d . . . C28 C 0.2311(4) 0.1659(4) 0.2064(2) 0.0238(12) Uani 1 1 d . A . C29 C 0.3771(11) 0.3142(8) 0.2988(4) 0.031(3) Uani 0.691(19) 1 d P A 1 H29A H 0.4425 0.2854 0.2812 0.037 Uiso 0.69 1 calc P A 1 H29B H 0.3898 0.3164 0.3437 0.037 Uiso 0.69 1 calc P A 1 C30 C 0.4032(8) 0.4430(9) 0.2909(3) 0.033(3) Uani 0.691(19) 1 d P A 1 H30A H 0.3299 0.4673 0.3020 0.039 Uiso 0.69 1 calc P A 1 H30B H 0.4063 0.4442 0.2469 0.039 Uiso 0.69 1 calc P A 1 C31 C 0.5367(19) 0.5330(17) 0.3335(10) 0.054(5) Uani 0.691(19) 1 d P A 1 H31A H 0.5542 0.6130 0.3264 0.082 Uiso 0.69 1 calc P A 1 H31B H 0.6085 0.5069 0.3237 0.082 Uiso 0.69 1 calc P A 1 H31C H 0.5312 0.5358 0.3773 0.082 Uiso 0.69 1 calc P A 1 C29B C 0.355(3) 0.360(3) 0.2851(13) 0.054(8) Uani 0.309(19) 1 d PU A 2 H29C H 0.3566 0.3913 0.2472 0.065 Uiso 0.31 1 calc P A 2 H29D H 0.3289 0.4126 0.3163 0.065 Uiso 0.31 1 calc P A 2 C30B C 0.479(3) 0.369(2) 0.3081(14) 0.075(10) Uani 0.309(19) 1 d P A 2 H30C H 0.5089 0.3228 0.2756 0.090 Uiso 0.31 1 calc P A 2 H30D H 0.4770 0.3329 0.3441 0.090 Uiso 0.31 1 calc P A 2 C31B C 0.585(5) 0.503(5) 0.330(3) 0.092(17) Uani 0.309(19) 1 d P A 2 H31D H 0.6680 0.5038 0.3517 0.139 Uiso 0.31 1 calc P A 2 H31E H 0.5510 0.5525 0.3574 0.139 Uiso 0.31 1 calc P A 2 H31F H 0.6008 0.5348 0.2929 0.139 Uiso 0.31 1 calc P A 2 C32 C 0.3679(5) 0.0771(4) 0.4250(2) 0.0263(12) Uani 1 1 d . . . H32A H 0.4078 0.0242 0.4030 0.032 Uiso 1 1 calc . . . H32B H 0.3187 0.0365 0.4541 0.032 Uiso 1 1 calc . . . C33 C 0.4767(5) 0.1978(5) 0.4613(2) 0.0411(15) Uani 1 1 d . . . H33A H 0.4362 0.2465 0.4863 0.049 Uiso 1 1 calc . . . H33B H 0.5170 0.2420 0.4313 0.049 Uiso 1 1 calc . . . C34 C 0.5861(5) 0.1818(5) 0.5050(2) 0.0395(14) Uani 1 1 d . . . H34A H 0.6525 0.2607 0.5273 0.059 Uiso 1 1 calc . . . H34B H 0.6284 0.1358 0.4803 0.059 Uiso 1 1 calc . . . H34C H 0.5469 0.1389 0.5351 0.059 Uiso 1 1 calc . . . C35 C 0.0747(5) 0.2845(4) 0.4414(2) 0.0351(13) Uani 1 1 d . . . H35A H 0.0835 0.2475 0.4766 0.042 Uiso 1 1 calc . . . H35B H 0.0159 0.3294 0.4488 0.042 Uiso 1 1 calc . . . C36 C 0.2111(5) 0.3693(5) 0.4361(3) 0.0418(15) Uani 1 1 d . . . H36A H 0.2012 0.4053 0.4006 0.050 Uiso 1 1 calc . . . H36B H 0.2684 0.3233 0.4280 0.050 Uiso 1 1 calc . . . C37 C 0.2780(7) 0.4714(6) 0.4975(3) 0.070(2) Uani 1 1 d . . . H37A H 0.3651 0.5239 0.4933 0.105 Uiso 1 1 calc . . . H37B H 0.2883 0.4357 0.5327 0.105 Uiso 1 1 calc . . . H37C H 0.2223 0.5182 0.5050 0.105 Uiso 1 1 calc . . . C38 C 0.0197(5) 0.4762(5) 0.2793(2) 0.0380(14) Uani 1 1 d . . . H38A H -0.0731 0.4708 0.2711 0.046 Uiso 1 1 calc . . . H38B H 0.0577 0.4912 0.2421 0.046 Uiso 1 1 calc . . . C39 C 0.1006(5) 0.5801(4) 0.3370(3) 0.0358(14) Uani 1 1 d . . . H39A H 0.1859 0.5727 0.3507 0.043 Uiso 1 1 calc . . . H39B H 0.1205 0.6573 0.3251 0.043 Uiso 1 1 calc . . . C40 C 0.0273(6) 0.5818(5) 0.3921(3) 0.0458(16) Uani 1 1 d . . . H40A H 0.0834 0.6480 0.4275 0.069 Uiso 1 1 calc . . . H40B H 0.0075 0.5057 0.4042 0.069 Uiso 1 1 calc . . . H40C H -0.0555 0.5927 0.3794 0.069 Uiso 1 1 calc . . . C41 C -0.3736(5) -0.0403(4) 0.1044(2) 0.0233(11) Uani 1 1 d . . . C42 C -0.1092(5) -0.3387(4) 0.2182(2) 0.0265(12) Uani 1 1 d . . . C43 C -0.5276(5) -0.3440(4) -0.0145(2) 0.0302(13) Uani 1 1 d . . . H43A H -0.5367 -0.3457 0.0290 0.036 Uiso 1 1 calc . . . H43B H -0.4388 -0.3434 -0.0192 0.036 Uiso 1 1 calc . . . C44 C -0.6375(5) -0.4574(4) -0.0609(2) 0.0295(13) Uani 1 1 d . . . H44A H -0.5956 -0.5004 -0.0885 0.035 Uiso 1 1 calc . . . H44B H -0.6865 -0.5124 -0.0371 0.035 Uiso 1 1 calc . . . C45 C -0.6755(5) -0.2305(4) -0.0169(2) 0.0252(12) Uani 1 1 d . . . H45A H -0.6892 -0.1612 -0.0288 0.030 Uiso 1 1 calc . . . H45B H -0.6773 -0.2224 0.0280 0.030 Uiso 1 1 calc . . . C46 C -0.7895(5) -0.3510(4) -0.0566(2) 0.0285(12) Uani 1 1 d . . . H46A H -0.8320 -0.3990 -0.0285 0.034 Uiso 1 1 calc . . . H46B H -0.8577 -0.3325 -0.0812 0.034 Uiso 1 1 calc . . . C47 C -0.5350(5) -0.2357(4) -0.0964(2) 0.0292(12) Uani 1 1 d . . . H47A H -0.4521 -0.2451 -0.1048 0.035 Uiso 1 1 calc . . . H47B H -0.5350 -0.1599 -0.1057 0.035 Uiso 1 1 calc . . . C48 C -0.6581(5) -0.3444(4) -0.1390(2) 0.0302(13) Uani 1 1 d . . . H48A H -0.7176 -0.3141 -0.1616 0.036 Uiso 1 1 calc . . . H48B H -0.6280 -0.3931 -0.1701 0.036 Uiso 1 1 calc . . . C49 C -0.1817(7) -0.5874(6) -0.1139(3) 0.0620(19) Uani 1 1 d . . . H49A H -0.1688 -0.6004 -0.1571 0.093 Uiso 1 1 calc . . . H49B H -0.2124 -0.6643 -0.1026 0.093 Uiso 1 1 calc . . . H49C H -0.0977 -0.5338 -0.0860 0.093 Uiso 1 1 calc . . . C50 C -0.2839(7) -0.5311(5) -0.1079(3) 0.0463(16) Uani 1 1 d . . . C51 C -0.4077(7) -0.2454(6) 0.2212(3) 0.066(2) Uani 1 1 d . . . H51A H -0.3821 -0.3131 0.2253 0.099 Uiso 1 1 calc . . . H51B H -0.3387 -0.1707 0.2469 0.099 Uiso 1 1 calc . . . H51C H -0.4182 -0.2415 0.1775 0.099 Uiso 1 1 calc . . . C52 C -0.5330(8) -0.2614(6) 0.2418(3) 0.063(2) Uani 1 1 d . . . C53 C -0.1196(5) -0.1750(5) 0.0912(3) 0.0388(14) Uani 1 1 d . . . H53A H -0.0475 -0.1153 0.1241 0.058 Uiso 1 1 calc . . . H53B H -0.1862 -0.2259 0.1101 0.058 Uiso 1 1 calc . . . H53C H -0.1605 -0.1342 0.0664 0.058 Uiso 1 1 calc . . . C54 C -0.0663(6) -0.2500(5) 0.0506(3) 0.0362(14) Uani 1 1 d . . . H1S H -0.463(6) -0.151(6) 0.009(3) 0.08(2) Uiso 1 1 d . . . H2S H -0.158(9) -0.467(8) 0.146(4) 0.16(4) Uiso 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 0.030(2) 0.0190(18) 0.0273(19) -0.0050(16) -0.0088(16) 0.0074(16) O2 0.0223(19) 0.0264(19) 0.0237(18) 0.0005(16) -0.0022(15) 0.0006(16) O3 0.0253(19) 0.0184(18) 0.0247(18) -0.0012(15) -0.0087(16) 0.0005(15) O4 0.029(2) 0.0235(18) 0.0231(18) -0.0024(16) 0.0009(16) 0.0053(16) O5 0.027(2) 0.0228(19) 0.0213(19) -0.0043(16) 0.0013(16) -0.0013(16) N1 0.019(2) 0.018(2) 0.023(2) -0.0014(19) -0.0056(19) 0.0013(18) N2 0.022(2) 0.018(2) 0.024(2) 0.0001(19) 0.0014(19) 0.0005(19) N3 0.045(4) 0.069(4) 0.094(5) 0.021(3) 0.033(3) 0.025(3) N4 0.050(4) 0.115(6) 0.091(5) -0.004(4) 0.010(4) 0.023(4) N5 0.060(4) 0.061(4) 0.045(3) 0.011(3) 0.017(3) 0.035(3) O6 0.025(2) 0.038(2) 0.0277(19) 0.0043(17) 0.0056(17) -0.0032(17) O7 0.030(2) 0.030(2) 0.053(2) -0.0095(19) 0.019(2) -0.0070(18) O8 0.027(2) 0.0225(19) 0.027(2) -0.0032(16) 0.0050(17) -0.0027(16) C1 0.019(3) 0.023(3) 0.028(3) 0.004(2) -0.005(2) 0.000(2) C2 0.025(3) 0.022(3) 0.029(3) 0.008(2) 0.000(2) 0.010(2) C3 0.022(3) 0.023(3) 0.016(2) 0.003(2) 0.001(2) 0.007(2) C4 0.019(3) 0.022(3) 0.021(3) 0.004(2) -0.002(2) 0.009(2) C5 0.019(3) 0.025(3) 0.022(3) 0.004(2) -0.002(2) 0.007(2) C6 0.026(3) 0.029(3) 0.019(3) 0.003(2) 0.002(2) 0.015(2) C7 0.025(3) 0.021(3) 0.021(3) 0.002(2) -0.006(2) 0.011(2) C8 0.029(3) 0.037(3) 0.025(3) -0.005(2) 0.000(2) 0.015(3) C9 0.029(3) 0.029(3) 0.018(3) -0.002(2) 0.002(2) 0.009(3) C10 0.025(3) 0.050(4) 0.021(3) 0.003(3) 0.001(2) 0.008(3) C11 0.028(3) 0.045(4) 0.025(3) 0.002(3) 0.013(3) -0.002(3) C12 0.039(3) 0.027(3) 0.022(3) 0.004(2) 0.006(3) 0.005(3) C13 0.025(3) 0.029(3) 0.013(2) -0.003(2) -0.001(2) 0.003(2) C14 0.028(3) 0.029(3) 0.015(3) -0.001(2) 0.005(2) 0.005(3) C15 0.031(3) 0.024(3) 0.019(3) 0.001(2) 0.001(2) 0.006(2) C16 0.031(3) 0.022(3) 0.019(3) 0.005(2) 0.001(2) 0.010(2) C17 0.024(3) 0.022(3) 0.024(3) 0.006(2) 0.002(2) 0.007(2) C18 0.019(3) 0.020(3) 0.025(3) 0.006(2) 0.002(2) 0.004(2) C19 0.023(3) 0.018(3) 0.021(3) 0.000(2) 0.001(2) 0.005(2) C20 0.018(3) 0.019(3) 0.024(3) 0.007(2) -0.006(2) 0.003(2) C21 0.021(3) 0.015(3) 0.022(3) 0.004(2) -0.006(2) 0.006(2) C22 0.017(3) 0.020(3) 0.029(3) 0.003(2) -0.001(2) 0.006(2) C23 0.014(3) 0.025(3) 0.029(3) 0.006(2) 0.002(2) 0.001(2) C24 0.023(3) 0.019(3) 0.030(3) 0.001(2) 0.008(2) 0.002(2) C25 0.025(3) 0.030(3) 0.023(3) 0.000(2) 0.006(2) -0.003(2) C26 0.019(3) 0.032(3) 0.024(3) 0.010(2) 0.002(2) -0.002(2) C27 0.013(3) 0.019(3) 0.027(3) 0.005(2) 0.006(2) -0.002(2) C28 0.011(3) 0.023(3) 0.026(3) 0.002(2) 0.001(2) -0.003(2) C29 0.035(7) 0.008(5) 0.032(5) 0.000(4) -0.014(4) -0.004(5) C30 0.031(5) 0.028(6) 0.031(5) 0.008(4) -0.005(4) 0.004(4) C31 0.058(12) 0.032(7) 0.044(7) 0.014(6) -0.021(8) -0.010(7) C29B 0.055(8) 0.035(8) 0.055(8) 0.010(2) 0.010(2) -0.001(3) C30B 0.051(19) 0.047(17) 0.13(2) 0.032(16) 0.029(17) 0.017(16) C31B 0.06(3) 0.08(4) 0.08(2) 0.00(2) -0.01(2) -0.02(2) C32 0.024(3) 0.026(3) 0.022(3) 0.003(2) -0.005(2) 0.005(2) C33 0.036(3) 0.029(3) 0.036(3) 0.000(3) -0.021(3) -0.002(3) C34 0.028(3) 0.039(3) 0.035(3) 0.000(3) -0.007(3) 0.002(3) C35 0.043(3) 0.024(3) 0.029(3) 0.001(2) -0.010(3) 0.010(3) C36 0.030(3) 0.031(3) 0.048(4) 0.006(3) -0.011(3) -0.001(3) C37 0.065(5) 0.040(4) 0.068(4) 0.001(3) -0.030(4) -0.004(3) C38 0.041(3) 0.028(3) 0.037(3) 0.004(3) -0.007(3) 0.011(3) C39 0.035(3) 0.021(3) 0.044(3) -0.003(3) -0.009(3) 0.012(3) C40 0.047(4) 0.037(3) 0.041(3) -0.009(3) -0.002(3) 0.014(3) C41 0.020(3) 0.025(3) 0.020(3) 0.000(2) -0.002(2) 0.006(2) C42 0.023(3) 0.020(3) 0.029(3) 0.002(2) 0.002(3) 0.004(2) C43 0.027(3) 0.025(3) 0.030(3) 0.002(2) -0.005(2) 0.005(2) C44 0.025(3) 0.019(3) 0.035(3) 0.000(2) -0.003(2) 0.003(2) C45 0.022(3) 0.022(3) 0.026(3) -0.001(2) 0.003(2) 0.005(2) C46 0.020(3) 0.020(3) 0.034(3) -0.001(2) 0.001(2) -0.001(2) C47 0.026(3) 0.026(3) 0.027(3) 0.004(2) 0.000(2) 0.002(2) C48 0.030(3) 0.023(3) 0.021(3) -0.001(2) 0.000(2) -0.006(2) C49 0.067(5) 0.061(4) 0.062(4) 0.017(4) 0.020(4) 0.025(4) C50 0.049(4) 0.041(4) 0.044(4) 0.010(3) 0.020(3) 0.009(3) C51 0.075(5) 0.070(5) 0.061(4) 0.012(4) 0.023(4) 0.034(4) C52 0.063(5) 0.069(5) 0.053(4) 0.008(4) -0.001(4) 0.026(5) C53 0.034(3) 0.034(3) 0.047(3) 0.012(3) 0.007(3) 0.011(3) C54 0.039(3) 0.035(3) 0.034(3) 0.014(3) 0.005(3) 0.011(3) _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 1.399(5) . ? O1 C38 1.445(6) . ? O2 C14 1.405(5) . ? O2 C35 1.441(5) . ? O3 C21 1.398(5) . ? O3 C32 1.432(5) . ? O4 C28 1.380(5) . ? O4 C29 1.435(11) . ? O4 C29B 1.55(3) . ? O5 C41 1.291(5) . ? N1 C47 1.484(6) . ? N1 C45 1.488(6) . ? N1 C43 1.493(6) . ? N2 C46 1.473(6) . ? N2 C44 1.478(6) . ? N2 C48 1.481(6) . ? N3 C50 1.094(7) . ? N4 C52 1.141(8) . ? N5 C54 1.134(6) . ? O6 C41 1.239(5) . ? O7 C42 1.231(5) . ? O8 C42 1.313(5) . ? C1 C27 1.515(6) . ? C1 C2 1.529(6) . ? C2 C3 1.400(6) . ? C2 C7 1.401(6) . ? C3 C4 1.401(6) . ? C4 C5 1.392(6) . ? C4 C41 1.520(6) . ? C5 C6 1.392(6) . ? C6 C7 1.404(6) . ? C6 C8 1.520(6) . ? C8 C9 1.513(7) . ? C9 C14 1.382(7) . ? C9 C10 1.407(7) . ? C10 C11 1.366(7) . ? C11 C12 1.384(7) . ? C12 C13 1.403(7) . ? C13 C14 1.398(7) . ? C13 C15 1.517(7) . ? C15 C16 1.522(6) . ? C16 C17 1.389(6) . ? C16 C21 1.409(6) . ? C17 C18 1.393(6) . ? C18 C19 1.397(6) . ? C18 C42 1.490(6) . ? C19 C20 1.393(6) . ? C20 C21 1.396(6) . ? C20 C22 1.529(6) . ? C22 C23 1.510(6) . ? C23 C28 1.400(6) . ? C23 C24 1.401(6) . ? C24 C25 1.378(7) . ? C25 C26 1.390(7) . ? C26 C27 1.392(6) . ? C27 C28 1.385(6) . ? C29 C30 1.521(14) . ? C30 C31 1.53(2) . ? C29B C30B 1.34(4) . ? C30B C31B 1.55(6) . ? C32 C33 1.508(6) . ? C33 C34 1.514(7) . ? C35 C36 1.504(7) . ? C36 C37 1.537(7) . ? C38 C39 1.517(7) . ? C39 C40 1.515(7) . ? C43 C44 1.537(6) . ? C45 C46 1.549(6) . ? C47 C48 1.542(6) . ? C49 C50 1.481(9) . ? C51 C52 1.435(10) . ? C53 C54 1.449(8) . ? 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 C7 O1 C38 112.4(3) . . ? C14 O2 C35 112.0(3) . . ? C21 O3 C32 113.0(3) . . ? C28 O4 C29 115.5(5) . . ? C28 O4 C29B 112.9(10) . . ? C29 O4 C29B 29.5(11) . . ? C47 N1 C45 110.3(4) . . ? C47 N1 C43 108.3(4) . . ? C45 N1 C43 109.0(4) . . ? C46 N2 C44 108.6(4) . . ? C46 N2 C48 109.5(4) . . ? C44 N2 C48 109.0(4) . . ? C27 C1 C2 110.6(4) . . ? C3 C2 C7 117.6(4) . . ? C3 C2 C1 118.6(4) . . ? C7 C2 C1 123.8(4) . . ? C2 C3 C4 121.4(4) . . ? C5 C4 C3 119.3(4) . . ? C5 C4 C41 119.9(4) . . ? C3 C4 C41 120.8(4) . . ? C4 C5 C6 120.9(4) . . ? C5 C6 C7 118.7(4) . . ? C5 C6 C8 118.3(4) . . ? C7 C6 C8 123.0(4) . . ? O1 C7 C2 120.1(4) . . ? O1 C7 C6 118.1(4) . . ? C2 C7 C6 121.7(4) . . ? C9 C8 C6 110.4(4) . . ? C14 C9 C10 117.4(5) . . ? C14 C9 C8 120.5(5) . . ? C10 C9 C8 121.9(5) . . ? C11 C10 C9 121.1(5) . . ? C10 C11 C12 120.7(5) . . ? C11 C12 C13 120.3(5) . . ? C14 C13 C12 117.5(5) . . ? C14 C13 C15 120.1(4) . . ? C12 C13 C15 121.9(5) . . ? C9 C14 C13 122.8(5) . . ? C9 C14 O2 118.7(4) . . ? C13 C14 O2 118.3(4) . . ? C13 C15 C16 108.4(4) . . ? C17 C16 C21 118.0(4) . . ? C17 C16 C15 118.6(4) . . ? C21 C16 C15 123.4(4) . . ? C16 C17 C18 121.4(4) . . ? C17 C18 C19 119.0(4) . . ? C17 C18 C42 118.5(4) . . ? C19 C18 C42 122.5(4) . . ? C20 C19 C18 121.6(4) . . ? C19 C20 C21 117.8(4) . . ? C19 C20 C22 119.1(4) . . ? C21 C20 C22 123.0(4) . . ? C20 C21 O3 118.8(4) . . ? C20 C21 C16 122.0(4) . . ? O3 C21 C16 119.2(4) . . ? C23 C22 C20 110.1(4) . . ? C28 C23 C24 118.0(5) . . ? C28 C23 C22 120.9(4) . . ? C24 C23 C22 120.9(4) . . ? C25 C24 C23 120.4(4) . . ? C24 C25 C26 120.0(4) . . ? C25 C26 C27 121.2(5) . . ? C28 C27 C26 117.8(4) . . ? C28 C27 C1 120.6(4) . . ? C26 C27 C1 121.4(4) . . ? O4 C28 C27 119.0(4) . . ? O4 C28 C23 118.5(4) . . ? C27 C28 C23 122.3(4) . . ? O4 C29 C30 112.3(8) . . ? C29 C30 C31 110.4(9) . . ? C30B C29B O4 116(3) . . ? C29B C30B C31B 114(3) . . ? O3 C32 C33 107.9(4) . . ? C32 C33 C34 112.3(4) . . ? O2 C35 C36 107.7(4) . . ? C35 C36 C37 110.8(5) . . ? O1 C38 C39 109.0(4) . . ? C40 C39 C38 112.8(4) . . ? O6 C41 O5 125.1(4) . . ? O6 C41 C4 120.1(4) . . ? O5 C41 C4 114.8(4) . . ? O7 C42 O8 123.6(4) . . ? O7 C42 C18 121.8(4) . . ? O8 C42 C18 114.6(4) . . ? N1 C43 C44 108.9(4) . . ? N2 C44 C43 110.6(4) . . ? N1 C45 C46 109.4(4) . . ? N2 C46 C45 109.7(4) . . ? N1 C47 C48 109.0(4) . . ? N2 C48 C47 110.1(4) . . ? N3 C50 C49 179.3(7) . . ? N4 C52 C51 178.4(8) . . ? N5 C54 C53 178.7(6) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.324 _refine_diff_density_min -0.324 _refine_diff_density_rms 0.071 data_4(BzNH2)2 _audit_creation_method SHELXL-97 _journal_name_full ; Chemistry, A European Journal ; _publ_section_title ; A Closer Look at the Conformational Behaviour of Calix[4]arene Dicarboxylic Acids and their (Supramolecular) Interactions with Aliphatic Amines e.g. (-)-Ephedrine ; _publ_contact_author_name ; Mikkel J\/orgensen ; _publ_contact_author_address ; Condensed Matter Physics and Chemistry Department Ris\/o National Laboratory DK-4000 Roskilde Denmark ; _publ_contact_author_email 'mikkel.joergensen@risoe.dk' loop_ _publ_author_name _publ_author_address 'Krebs, Frederik C.' ; Department of Chemistry Technical University of Denmark DK-2800 Lyngby Denmark ; 'Sommer-Larsen, Peter' ; Condensed Matter Physics and Chemistry Department Ris\/o National Laboratory DK-4000 Roskilde Denmark ; 'J\/orgensen, Mikkel' ; Condensed Matter Physics and Chemistry Department Ris\/o National Laboratory DK-4000 Roskilde Denmark ; _chemical_name_systematic ; 11,23-dibromo- 25,26,27,28-tetrapropoxycalix[4]arene- 5,17-dicarboxylic acid bis-benzylamine salt ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C57 H66 Br2 Cl2 N2 O8' _chemical_formula_weight 1137.84 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Br' 'Br' -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 24.817(5) _cell_length_b 25.026(5) _cell_length_c 17.854(4) _cell_angle_alpha 90.00 _cell_angle_beta 99.88(3) _cell_angle_gamma 90.00 _cell_volume 10924(4) _cell_formula_units_Z 8 _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 0.50 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.384 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 4720 _exptl_absorpt_coefficient_mu 1.637 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details 'SADABS (Sheldrick)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Siemens SMART CCD' _diffrn_measurement_method 'omega scan, frame data integration' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 45803 _diffrn_reflns_av_R_equivalents 0.0986 _diffrn_reflns_av_sigmaI/netI 0.0970 _diffrn_reflns_limit_h_min -30 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min -31 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.16 _diffrn_reflns_theta_max 26.37 _reflns_number_total 11155 _reflns_number_gt 6087 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART Siemens' _computing_cell_refinement 'SAINT Siemens' _computing_data_reduction 'SAINT Siemens' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Sheldrick)' _computing_publication_material 'XCIF (Sheldrick)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0629P)^2^+80.3334P] 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 11155 _refine_ls_number_parameters 650 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1613 _refine_ls_R_factor_gt 0.0814 _refine_ls_wR_factor_ref 0.2043 _refine_ls_wR_factor_gt 0.1650 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _refine_ls_shift/su_max 0.033 _refine_ls_shift/su_mean 0.003 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 Br1 Br 0.20698(3) 0.19378(3) 0.54955(4) 0.0522(2) Uani 1 1 d . . . Br2 Br 0.29338(4) 0.03627(3) 0.46876(5) 0.0740(3) Uani 1 1 d . . . Cl1 Cl 0.75827(12) 0.01593(12) 0.73071(18) 0.1109(10) Uani 1 1 d . . . Cl2 Cl 0.7411(3) -0.0484(2) 0.8526(3) 0.253(3) Uani 1 1 d . . . N1 N 0.08141(19) 0.33189(18) 0.6688(3) 0.0337(11) Uani 1 1 d . . . H1A H 0.0472 0.3256 0.6461 0.051 Uiso 1 1 calc . . . H1B H 0.0882 0.3668 0.6680 0.051 Uiso 1 1 calc . . . H1C H 0.0858 0.3207 0.7168 0.051 Uiso 1 1 calc . . . N2 N 0.5722(2) -0.08881(19) 0.8628(3) 0.0421(13) Uani 1 1 d . . . H2A H 0.5448 -0.0666 0.8455 0.063 Uiso 1 1 calc . . . H2B H 0.5589 -0.1213 0.8683 0.063 Uiso 1 1 calc . . . H2C H 0.5953 -0.0901 0.8298 0.063 Uiso 1 1 calc . . . O1 O 0.07894(18) 0.30260(16) 0.8146(2) 0.0423(11) Uani 1 1 d . . . O2 O 0.02055(17) 0.30058(16) 0.8962(2) 0.0392(10) Uani 1 1 d . . . O3 O 0.5314(2) -0.05914(16) 0.6293(2) 0.0440(11) Uani 1 1 d . . . O4 O 0.60168(18) -0.05613(16) 0.7234(3) 0.0433(11) Uani 1 1 d . . . O5 O 0.04965(16) 0.06722(15) 0.7015(2) 0.0337(9) Uani 1 1 d . . . O6 O 0.07914(16) 0.05437(14) 0.8923(2) 0.0320(9) Uani 1 1 d . . . O7 O 0.44695(18) 0.17920(16) 0.6738(2) 0.0400(10) Uani 1 1 d . . . O8 O 0.56981(17) 0.19232(15) 0.6488(2) 0.0375(10) Uani 1 1 d . . . C1 C 0.0115(2) 0.1029(2) 0.5527(3) 0.0331(14) Uani 1 1 d . . . H1D H 0.0079 0.1130 0.4997 0.040 Uiso 1 1 calc . . . H1E H 0.0037 0.0650 0.5550 0.040 Uiso 1 1 calc . . . C2 C 0.0694(2) 0.1137(2) 0.5928(3) 0.0282(13) Uani 1 1 d . . . C3 C 0.1065(3) 0.1433(2) 0.5590(3) 0.0345(14) Uani 1 1 d . . . H3 H 0.0974 0.1533 0.5083 0.041 Uiso 1 1 calc . . . C4 C 0.1559(2) 0.1574(2) 0.5999(3) 0.0338(14) Uani 1 1 d . . . C5 C 0.1700(2) 0.1459(2) 0.6765(3) 0.0334(14) Uani 1 1 d . . . H5 H 0.2032 0.1575 0.7039 0.040 Uiso 1 1 calc . . . C6 C 0.1336(2) 0.1166(2) 0.7120(3) 0.0296(13) Uani 1 1 d . . . C7 C 0.0855(2) 0.0983(2) 0.6683(3) 0.0299(13) Uani 1 1 d . . . C8 C 0.1443(2) 0.1085(2) 0.7973(3) 0.0325(13) Uani 1 1 d . . . H8A H 0.1437 0.0705 0.8082 0.039 Uiso 1 1 calc . . . H8B H 0.1805 0.1219 0.8180 0.039 Uiso 1 1 calc . . . C9 C 0.1026(2) 0.1365(2) 0.8358(3) 0.0288(13) Uani 1 1 d . . . C10 C 0.0945(2) 0.1910(2) 0.8270(3) 0.0281(12) Uani 1 1 d . . . H10 H 0.1154 0.2102 0.7977 0.034 Uiso 1 1 calc . . . C11 C 0.0558(2) 0.2179(2) 0.8607(3) 0.0250(12) Uani 1 1 d . . . C12 C 0.0226(2) 0.1887(2) 0.9007(3) 0.0274(12) Uani 1 1 d . . . H12 H -0.0043 0.2062 0.9218 0.033 Uiso 1 1 calc . . . C13 C 0.0286(2) 0.1343(2) 0.9098(3) 0.0274(12) Uani 1 1 d . . . C14 C 0.0702(2) 0.1091(2) 0.8792(3) 0.0285(13) Uani 1 1 d . . . C15 C 0.6466(3) 0.1427(2) 0.7699(4) 0.0392(15) Uani 1 1 d . . . H15A H 0.6838 0.1333 0.7653 0.047 Uiso 1 1 calc . . . H15B H 0.6419 0.1808 0.7608 0.047 Uiso 1 1 calc . . . C16 C 0.3635(3) 0.1295(2) 0.6510(3) 0.0382(15) Uani 1 1 d . . . C17 C 0.3284(3) 0.0968(3) 0.6029(4) 0.0436(16) Uani 1 1 d . . . H17 H 0.2948 0.0873 0.6152 0.052 Uiso 1 1 calc . . . C18 C 0.3433(3) 0.0783(3) 0.5360(4) 0.0466(17) Uani 1 1 d . . . C19 C 0.3934(3) 0.0901(2) 0.5179(3) 0.0403(16) Uani 1 1 d . . . H19 H 0.4033 0.0755 0.4744 0.048 Uiso 1 1 calc . . . C20 C 0.4295(3) 0.1235(2) 0.5640(3) 0.0353(14) Uani 1 1 d . . . C21 C 0.4122(3) 0.1450(2) 0.6289(3) 0.0342(14) Uani 1 1 d . . . C22 C 0.4862(3) 0.1349(2) 0.5483(3) 0.0383(15) Uani 1 1 d . . . H22A H 0.4924 0.1732 0.5498 0.046 Uiso 1 1 calc . . . H22B H 0.4890 0.1224 0.4976 0.046 Uiso 1 1 calc . . . C23 C 0.5299(2) 0.1078(2) 0.6060(3) 0.0315(13) Uani 1 1 d . . . C24 C 0.5301(2) 0.0527(2) 0.6134(3) 0.0308(13) Uani 1 1 d . . . H24 H 0.5043 0.0328 0.5810 0.037 Uiso 1 1 calc . . . C25 C 0.5676(2) 0.0264(2) 0.6676(3) 0.0286(13) Uani 1 1 d . . . C26 C 0.6051(2) 0.0565(2) 0.7166(3) 0.0312(13) Uani 1 1 d . . . H26 H 0.6299 0.0392 0.7538 0.037 Uiso 1 1 calc . . . C27 C 0.6065(2) 0.1119(2) 0.7115(3) 0.0328(14) Uani 1 1 d . . . C28 C 0.5693(3) 0.1366(2) 0.6549(3) 0.0337(14) Uani 1 1 d . . . C29 C 0.0508(2) 0.2778(2) 0.8565(3) 0.0323(14) Uani 1 1 d . . . C30 C 0.5668(3) -0.0340(2) 0.6741(3) 0.0317(13) Uani 1 1 d . . . C31 C 0.0671(3) 0.0125(2) 0.7151(3) 0.0373(14) Uani 1 1 d . . . H31A H 0.0512 -0.0015 0.7570 0.045 Uiso 1 1 calc . . . H31B H 0.1066 0.0119 0.7303 0.045 Uiso 1 1 calc . . . C32 C 0.0516(3) -0.0231(3) 0.6474(4) 0.0461(17) Uani 1 1 d . . . H32A H 0.0663 -0.0087 0.6047 0.055 Uiso 1 1 calc . . . H32B H 0.0121 -0.0242 0.6335 0.055 Uiso 1 1 calc . . . C33 C 0.0737(4) -0.0799(3) 0.6652(4) 0.064(2) Uani 1 1 d . . . H33A H 0.0632 -0.1022 0.6214 0.095 Uiso 1 1 calc . . . H33B H 0.0589 -0.0941 0.7073 0.095 Uiso 1 1 calc . . . H33C H 0.1129 -0.0787 0.6779 0.095 Uiso 1 1 calc . . . C34 C 0.1200(3) 0.0448(2) 0.9583(3) 0.0377(15) Uani 1 1 d . C . H34A H 0.1093 0.0615 1.0025 0.045 Uiso 1 1 calc . . . H34B H 0.1547 0.0601 0.9510 0.045 Uiso 1 1 calc . . . C35 C 0.1261(3) -0.0142(2) 0.9706(4) 0.0457(17) Uani 1 1 d . . . H35A H 0.1539 -0.0203 1.0150 0.055 Uiso 1 1 calc . A 1 H35B H 0.0919 -0.0281 0.9819 0.055 Uiso 1 1 calc . B 1 C36 C 0.1407(4) -0.0448(3) 0.9070(5) 0.048(3) Uani 0.795(17) 1 d P C 1 H36A H 0.1442 -0.0819 0.9205 0.072 Uiso 0.79 1 calc P C 1 H36B H 0.1748 -0.0319 0.8956 0.072 Uiso 0.79 1 calc P C 1 H36C H 0.1126 -0.0405 0.8631 0.072 Uiso 0.79 1 calc P C 1 C36U C 0.1737(18) -0.0226(16) 1.041(3) 0.088(19) Uani 0.205(17) 1 d P C 2 H36D H 0.1788 -0.0601 1.0514 0.132 Uiso 0.21 1 calc P C 2 H36E H 0.1641 -0.0053 1.0852 0.132 Uiso 0.21 1 calc P C 2 H36F H 0.2070 -0.0075 1.0303 0.132 Uiso 0.21 1 calc P C 2 C37 C 0.4261(4) 0.2347(4) 0.6760(5) 0.084(3) Uani 1 1 d . . . H37A H 0.3876 0.2354 0.6536 0.101 Uiso 1 1 calc . . . H37B H 0.4293 0.2461 0.7285 0.101 Uiso 1 1 calc . . . C38 C 0.4540(4) 0.2700(4) 0.6376(6) 0.088(3) Uani 1 1 d . . . H38A H 0.4450 0.2633 0.5834 0.106 Uiso 1 1 calc . . . H38B H 0.4931 0.2647 0.6531 0.106 Uiso 1 1 calc . . . C39 C 0.4389(3) 0.3283(3) 0.6546(4) 0.0556(19) Uani 1 1 d . . . H39A H 0.4582 0.3524 0.6268 0.083 Uiso 1 1 calc . . . H39B H 0.4490 0.3351 0.7080 0.083 Uiso 1 1 calc . . . H39C H 0.4003 0.3333 0.6394 0.083 Uiso 1 1 calc . . . C40 C 0.6040(3) 0.2119(2) 0.5977(3) 0.0404(16) Uani 1 1 d . . . H40A H 0.5934 0.1956 0.5480 0.049 Uiso 1 1 calc . . . H40B H 0.6419 0.2028 0.6166 0.049 Uiso 1 1 calc . . . C41 C 0.5978(3) 0.2710(2) 0.5915(4) 0.0459(17) Uani 1 1 d . . . H41A H 0.6037 0.2864 0.6420 0.055 Uiso 1 1 calc . . . H41B H 0.5607 0.2795 0.5673 0.055 Uiso 1 1 calc . . . C42 C 0.6375(3) 0.2956(3) 0.5462(4) 0.056(2) Uani 1 1 d . . . H42A H 0.6317 0.3335 0.5427 0.083 Uiso 1 1 calc . . . H42B H 0.6318 0.2805 0.4960 0.083 Uiso 1 1 calc . . . H42C H 0.6743 0.2885 0.5710 0.083 Uiso 1 1 calc . . . C43 C 0.1198(2) 0.3029(2) 0.6282(3) 0.0358(14) Uani 1 1 d . . . H43A H 0.1150 0.3157 0.5762 0.043 Uiso 1 1 calc . . . H43B H 0.1108 0.2652 0.6267 0.043 Uiso 1 1 calc . . . C44 C 0.1787(2) 0.3097(2) 0.6643(3) 0.0316(13) Uani 1 1 d . . . C45 C 0.1978(3) 0.2932(3) 0.7379(4) 0.0494(18) Uani 1 1 d . . . H45 H 0.1733 0.2797 0.7673 0.059 Uiso 1 1 calc . . . C46 C 0.2522(3) 0.2965(4) 0.7680(4) 0.072(3) Uani 1 1 d . . . H46 H 0.2646 0.2848 0.8174 0.086 Uiso 1 1 calc . . . C47 C 0.2892(3) 0.3171(4) 0.7254(5) 0.072(3) Uani 1 1 d . . . H47 H 0.3259 0.3205 0.7467 0.087 Uiso 1 1 calc . . . C48 C 0.2711(3) 0.3323(3) 0.6522(4) 0.058(2) Uani 1 1 d . . . H48 H 0.2958 0.3450 0.6226 0.069 Uiso 1 1 calc . . . C49 C 0.2159(3) 0.3289(3) 0.6215(4) 0.0460(16) Uani 1 1 d . . . H49 H 0.2038 0.3398 0.5717 0.055 Uiso 1 1 calc . . . C50 C 0.6011(3) -0.0696(3) 0.9366(4) 0.0487(18) Uani 1 1 d . . . H50A H 0.5752 -0.0682 0.9716 0.058 Uiso 1 1 calc . . . H50B H 0.6134 -0.0334 0.9301 0.058 Uiso 1 1 calc . . . C51 C 0.6493(3) -0.1021(3) 0.9723(4) 0.0456(17) Uani 1 1 d . . . C52 C 0.6738(3) -0.1413(4) 0.9349(5) 0.074(3) Uani 1 1 d . . . H52 H 0.6602 -0.1482 0.8840 0.089 Uiso 1 1 calc . . . C53 C 0.7178(4) -0.1701(4) 0.9710(6) 0.097(4) Uani 1 1 d . . . H53 H 0.7328 -0.1969 0.9449 0.116 Uiso 1 1 calc . . . C54 C 0.7398(3) -0.1596(4) 1.0452(5) 0.087(3) Uani 1 1 d . . . H54 H 0.7710 -0.1775 1.0688 0.104 Uiso 1 1 calc . . . C55 C 0.7150(3) -0.1224(3) 1.0839(4) 0.059(2) Uani 1 1 d . . . H55 H 0.7288 -0.1157 1.1348 0.071 Uiso 1 1 calc . . . C56 C 0.6700(3) -0.0948(3) 1.0482(4) 0.0447(16) Uani 1 1 d . . . H56 H 0.6530 -0.0705 1.0760 0.054 Uiso 1 1 calc . . . C57 C 0.7327(3) -0.0439(4) 0.7584(5) 0.079(3) Uani 1 1 d . . . H57A H 0.6941 -0.0465 0.7373 0.095 Uiso 1 1 calc . . . H57B H 0.7514 -0.0734 0.7386 0.095 Uiso 1 1 calc . . . 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 Br1 0.0555(4) 0.0435(4) 0.0670(5) -0.0011(4) 0.0366(4) -0.0044(3) Br2 0.0829(6) 0.0550(5) 0.0700(6) -0.0044(4) -0.0265(5) -0.0014(4) Cl1 0.095(2) 0.107(2) 0.134(2) 0.0228(18) 0.0278(18) -0.0247(16) Cl2 0.424(10) 0.228(6) 0.126(3) 0.038(4) 0.103(5) -0.031(6) N1 0.036(3) 0.027(3) 0.039(3) 0.005(2) 0.011(2) 0.001(2) N2 0.069(4) 0.027(3) 0.030(3) 0.000(2) 0.009(3) -0.005(3) O1 0.052(3) 0.028(2) 0.048(3) 0.004(2) 0.012(2) -0.003(2) O2 0.049(3) 0.031(2) 0.039(2) -0.0093(19) 0.008(2) 0.011(2) O3 0.068(3) 0.025(2) 0.039(2) -0.0069(19) 0.011(2) -0.004(2) O4 0.044(3) 0.032(2) 0.056(3) 0.017(2) 0.015(2) 0.004(2) O5 0.040(2) 0.034(2) 0.029(2) -0.0012(18) 0.0142(18) -0.0035(19) O6 0.041(2) 0.023(2) 0.032(2) -0.0011(17) 0.0050(18) 0.0051(18) O7 0.053(3) 0.032(2) 0.037(2) -0.0066(19) 0.016(2) 0.002(2) O8 0.059(3) 0.026(2) 0.034(2) 0.0045(18) 0.024(2) -0.003(2) C1 0.042(4) 0.036(3) 0.022(3) -0.006(3) 0.008(3) -0.003(3) C2 0.036(3) 0.025(3) 0.027(3) -0.003(2) 0.013(2) 0.003(3) C3 0.046(4) 0.031(3) 0.030(3) -0.003(3) 0.017(3) 0.007(3) C4 0.036(3) 0.024(3) 0.045(4) -0.001(3) 0.019(3) 0.004(3) C5 0.032(3) 0.028(3) 0.042(4) -0.008(3) 0.010(3) 0.004(3) C6 0.030(3) 0.028(3) 0.032(3) -0.009(3) 0.007(2) 0.006(3) C7 0.031(3) 0.030(3) 0.033(3) -0.003(3) 0.016(3) 0.005(3) C8 0.030(3) 0.035(3) 0.034(3) -0.010(3) 0.009(3) 0.004(3) C9 0.027(3) 0.033(3) 0.026(3) -0.005(2) 0.002(2) 0.004(3) C10 0.032(3) 0.033(3) 0.020(3) -0.001(2) 0.006(2) 0.000(3) C11 0.029(3) 0.028(3) 0.017(3) -0.001(2) -0.001(2) 0.002(2) C12 0.028(3) 0.031(3) 0.023(3) -0.002(2) 0.002(2) 0.005(2) C13 0.030(3) 0.031(3) 0.021(3) 0.001(2) 0.004(2) 0.001(3) C14 0.036(3) 0.022(3) 0.025(3) -0.004(2) 0.001(2) 0.001(3) C15 0.041(4) 0.035(4) 0.043(4) -0.002(3) 0.011(3) -0.007(3) C16 0.040(4) 0.039(4) 0.037(3) 0.009(3) 0.011(3) 0.013(3) C17 0.039(4) 0.041(4) 0.046(4) 0.011(3) -0.006(3) 0.004(3) C18 0.056(5) 0.041(4) 0.036(4) 0.001(3) -0.011(3) 0.008(3) C19 0.060(4) 0.033(3) 0.024(3) 0.002(3) -0.003(3) 0.014(3) C20 0.055(4) 0.028(3) 0.023(3) 0.008(3) 0.005(3) 0.012(3) C21 0.051(4) 0.023(3) 0.026(3) 0.003(3) 0.001(3) 0.009(3) C22 0.065(4) 0.030(3) 0.021(3) 0.003(3) 0.013(3) 0.003(3) C23 0.047(4) 0.032(3) 0.020(3) 0.001(2) 0.018(3) 0.000(3) C24 0.045(4) 0.029(3) 0.021(3) -0.003(2) 0.016(3) -0.005(3) C25 0.036(3) 0.031(3) 0.025(3) 0.001(2) 0.022(3) 0.001(3) C26 0.035(3) 0.032(3) 0.030(3) 0.006(3) 0.014(3) 0.000(3) C27 0.041(3) 0.032(3) 0.031(3) 0.000(3) 0.020(3) -0.004(3) C28 0.054(4) 0.020(3) 0.034(3) 0.002(3) 0.028(3) 0.001(3) C29 0.037(3) 0.028(3) 0.028(3) 0.002(3) -0.007(3) -0.001(3) C30 0.040(3) 0.026(3) 0.036(3) 0.006(3) 0.025(3) 0.001(3) C31 0.039(4) 0.036(4) 0.038(4) 0.003(3) 0.009(3) -0.002(3) C32 0.065(5) 0.042(4) 0.032(3) -0.001(3) 0.011(3) -0.006(3) C33 0.100(7) 0.034(4) 0.055(5) 0.003(3) 0.009(4) -0.001(4) C34 0.057(4) 0.027(3) 0.025(3) 0.003(3) -0.002(3) 0.004(3) C35 0.054(4) 0.033(4) 0.048(4) 0.008(3) 0.001(3) 0.005(3) C36 0.052(6) 0.036(5) 0.056(6) 0.005(4) 0.009(4) 0.006(4) C36U 0.08(3) 0.06(3) 0.10(4) 0.05(2) -0.05(3) -0.02(2) C37 0.093(7) 0.081(7) 0.078(6) 0.007(5) 0.011(5) -0.024(6) C38 0.087(7) 0.093(7) 0.088(7) 0.010(6) 0.024(6) 0.012(6) C39 0.083(6) 0.034(4) 0.051(4) 0.005(3) 0.017(4) 0.007(4) C40 0.052(4) 0.035(3) 0.041(4) 0.009(3) 0.026(3) -0.010(3) C41 0.066(5) 0.031(4) 0.043(4) 0.003(3) 0.016(3) -0.012(3) C42 0.058(5) 0.060(5) 0.045(4) 0.023(4) 0.002(3) -0.024(4) C43 0.038(3) 0.039(4) 0.031(3) -0.002(3) 0.008(3) 0.004(3) C44 0.032(3) 0.030(3) 0.034(3) -0.006(3) 0.011(3) 0.002(3) C45 0.039(4) 0.079(5) 0.031(4) 0.008(3) 0.008(3) -0.001(4) C46 0.043(4) 0.133(8) 0.037(4) 0.006(5) 0.000(3) 0.001(5) C47 0.038(4) 0.122(8) 0.058(5) -0.017(5) 0.010(4) -0.004(5) C48 0.043(4) 0.078(5) 0.057(5) 0.002(4) 0.021(4) -0.009(4) C49 0.048(4) 0.052(4) 0.039(4) 0.005(3) 0.011(3) 0.001(3) C50 0.061(5) 0.053(4) 0.035(4) -0.013(3) 0.014(3) -0.008(4) C51 0.034(4) 0.060(4) 0.047(4) -0.015(3) 0.018(3) -0.005(3) C52 0.041(4) 0.121(8) 0.062(5) -0.049(5) 0.009(4) -0.003(5) C53 0.051(5) 0.142(9) 0.094(7) -0.065(7) 0.003(5) 0.026(6) C54 0.039(5) 0.118(8) 0.096(7) -0.056(6) -0.009(4) 0.022(5) C55 0.041(4) 0.079(6) 0.057(5) -0.019(4) 0.006(4) -0.001(4) C56 0.040(4) 0.053(4) 0.045(4) -0.009(3) 0.019(3) -0.006(3) C57 0.058(5) 0.100(7) 0.084(6) 0.003(5) 0.022(5) 0.002(5) _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 Br1 C4 1.907(6) . ? Br2 C18 1.891(7) . ? Cl1 C57 1.731(10) . ? Cl2 C57 1.662(10) . ? N1 C43 1.482(7) . ? N2 C50 1.468(8) . ? O1 C29 1.268(7) . ? O2 C29 1.254(7) . ? O3 C30 1.253(7) . ? O4 C30 1.253(7) . ? O5 C7 1.388(6) . ? O5 C31 1.443(7) . ? O6 C14 1.401(6) . ? O6 C34 1.438(7) . ? O7 C21 1.370(7) . ? O7 C37 1.486(11) . ? O8 C28 1.399(7) . ? O8 C40 1.435(6) . ? C1 C13 1.512(8) 2_556 ? C1 C2 1.515(8) . ? C2 C3 1.395(8) . ? C2 C7 1.392(8) . ? C3 C4 1.361(8) . ? C4 C5 1.382(8) . ? C5 C6 1.397(8) . ? C6 C7 1.388(8) . ? C6 C8 1.513(8) . ? C8 C9 1.510(7) . ? C9 C10 1.385(8) . ? C9 C14 1.389(8) . ? C10 C11 1.390(7) . ? C11 C12 1.389(7) . ? C11 C29 1.505(8) . ? C12 C13 1.376(8) . ? C13 C14 1.399(7) . ? C13 C1 1.512(8) 2_556 ? C15 C16 1.511(8) 2_656 ? C15 C27 1.521(8) . ? C16 C17 1.382(9) . ? C16 C21 1.390(8) . ? C16 C15 1.511(8) 2_656 ? C17 C18 1.387(9) . ? C18 C19 1.369(9) . ? C19 C20 1.388(9) . ? C20 C21 1.411(8) . ? C20 C22 1.506(9) . ? C22 C23 1.522(8) . ? C23 C24 1.385(8) . ? C23 C28 1.394(8) . ? C24 C25 1.390(8) . ? C25 C26 1.385(8) . ? C25 C30 1.516(8) . ? C26 C27 1.389(8) . ? C27 C28 1.392(8) . ? C31 C32 1.498(9) . ? C32 C33 1.537(10) . ? C34 C35 1.497(8) . ? C35 C36 1.466(11) . ? C35 C36U 1.59(3) . ? C37 C38 1.376(12) . ? C38 C39 1.549(12) . ? C40 C41 1.489(9) . ? C41 C42 1.511(9) . ? C43 C44 1.503(8) . ? C44 C49 1.381(8) . ? C44 C45 1.381(8) . ? C45 C46 1.369(10) . ? C46 C47 1.387(11) . ? C47 C48 1.362(11) . ? C48 C49 1.388(10) . ? C50 C51 1.495(10) . ? C51 C56 1.376(9) . ? C51 C52 1.384(10) . ? C52 C53 1.373(12) . ? C53 C54 1.368(12) . ? C54 C55 1.368(10) . ? C55 C56 1.375(10) . ? 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 C7 O5 C31 114.1(4) . . ? C14 O6 C34 111.7(4) . . ? C21 O7 C37 114.4(5) . . ? C28 O8 C40 113.8(4) . . ? C13 C1 C2 109.9(4) 2_556 . ? C3 C2 C7 117.7(5) . . ? C3 C2 C1 122.2(5) . . ? C7 C2 C1 119.9(5) . . ? C4 C3 C2 120.4(5) . . ? C3 C4 C5 121.9(5) . . ? C3 C4 Br1 118.8(5) . . ? C5 C4 Br1 119.3(5) . . ? C4 C5 C6 119.0(5) . . ? C7 C6 C5 118.6(5) . . ? C7 C6 C8 120.4(5) . . ? C5 C6 C8 120.8(5) . . ? C6 C7 O5 119.8(5) . . ? C6 C7 C2 121.9(5) . . ? O5 C7 C2 118.1(5) . . ? C9 C8 C6 112.4(5) . . ? C10 C9 C14 117.6(5) . . ? C10 C9 C8 120.3(5) . . ? C14 C9 C8 122.2(5) . . ? C9 C10 C11 121.7(5) . . ? C12 C11 C10 118.8(5) . . ? C12 C11 C29 120.0(5) . . ? C10 C11 C29 121.2(5) . . ? C13 C12 C11 121.4(5) . . ? C12 C13 C14 118.1(5) . . ? C12 C13 C1 120.1(5) . 2_556 ? C14 C13 C1 121.7(5) . 2_556 ? C9 C14 C13 122.2(5) . . ? C9 C14 O6 119.0(5) . . ? C13 C14 O6 118.8(5) . . ? C16 C15 C27 109.6(5) 2_656 . ? C17 C16 C21 118.4(6) . . ? C17 C16 C15 121.5(6) . 2_656 ? C21 C16 C15 119.7(6) . 2_656 ? C16 C17 C18 120.0(6) . . ? C19 C18 C17 121.2(6) . . ? C19 C18 Br2 119.5(5) . . ? C17 C18 Br2 119.4(6) . . ? C18 C19 C20 120.7(6) . . ? C19 C20 C21 117.3(6) . . ? C19 C20 C22 122.2(5) . . ? C21 C20 C22 120.4(6) . . ? O7 C21 C16 119.9(5) . . ? O7 C21 C20 117.9(6) . . ? C16 C21 C20 121.9(6) . . ? C20 C22 C23 111.6(5) . . ? C24 C23 C28 117.7(5) . . ? C24 C23 C22 119.9(5) . . ? C28 C23 C22 122.4(5) . . ? C23 C24 C25 121.9(5) . . ? C26 C25 C24 118.7(5) . . ? C26 C25 C30 120.6(5) . . ? C24 C25 C30 120.7(5) . . ? C25 C26 C27 121.5(6) . . ? C26 C27 C28 118.0(6) . . ? C26 C27 C15 118.8(5) . . ? C28 C27 C15 123.1(5) . . ? C27 C28 C23 122.1(5) . . ? C27 C28 O8 119.1(5) . . ? C23 C28 O8 118.7(5) . . ? O2 C29 O1 123.7(5) . . ? O2 C29 C11 118.4(5) . . ? O1 C29 C11 117.8(5) . . ? O4 C30 O3 123.4(5) . . ? O4 C30 C25 118.6(6) . . ? O3 C30 C25 118.0(5) . . ? O5 C31 C32 113.6(5) . . ? C31 C32 C33 110.5(5) . . ? O6 C34 C35 108.9(5) . . ? C36 C35 C34 115.6(6) . . ? C36 C35 C36U 107(2) . . ? C34 C35 C36U 106.8(15) . . ? C38 C37 O7 112.2(8) . . ? C37 C38 C39 110.2(8) . . ? O8 C40 C41 108.7(5) . . ? C40 C41 C42 112.1(6) . . ? N1 C43 C44 113.3(5) . . ? C49 C44 C45 118.6(6) . . ? C49 C44 C43 119.6(5) . . ? C45 C44 C43 121.5(5) . . ? C46 C45 C44 120.6(6) . . ? C45 C46 C47 120.6(7) . . ? C48 C47 C46 119.4(7) . . ? C47 C48 C49 120.1(7) . . ? C44 C49 C48 120.7(6) . . ? N2 C50 C51 115.9(5) . . ? C56 C51 C52 116.6(7) . . ? C56 C51 C50 118.9(6) . . ? C52 C51 C50 124.5(6) . . ? C53 C52 C51 121.7(7) . . ? C54 C53 C52 120.5(8) . . ? C53 C54 C55 118.6(8) . . ? C54 C55 C56 120.6(7) . . ? C51 C56 C55 121.8(6) . . ? Cl2 C57 Cl1 111.1(6) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.625 _refine_diff_density_min -0.779 _refine_diff_density_rms 0.090 data_4(Et2NH)2,I _audit_creation_method SHELXL-97 _journal_name_full ; Chemistry, A European Journal ; _publ_section_title ; A Closer Look at the Conformational Behaviour of Calix[4]arene Dicarboxylic Acids and their (Supramolecular) Interactions with Aliphatic Amines e.g. (-)-Ephedrine ; _publ_contact_author_name ; Mikkel J\/orgensen ; _publ_contact_author_address ; Condensed Matter Physics and Chemistry Department Ris\/o National Laboratory DK-4000 Roskilde Denmark ; _publ_contact_author_email 'mikkel.joergensen@risoe.dk' loop_ _publ_author_name _publ_author_address 'Krebs, Frederik C.' ; Department of Chemistry Technical University of Denmark DK-2800 Lyngby Denmark ; 'Sommer-Larsen, Peter' ; Condensed Matter Physics and Chemistry Department Ris\/o National Laboratory DK-4000 Roskilde Denmark ; 'J\/orgensen, Mikkel' ; Condensed Matter Physics and Chemistry Department Ris\/o National Laboratory DK-4000 Roskilde Denmark ; _chemical_name_systematic ; 11,23-dibromo- 25,26,27,28-tetrapropoxycalix[4]arene- 5,17-dicarboxylic acid bis-diethylamine salt ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C53 H73 Br2 Cl2 N3 O8' _chemical_formula_weight 1110.86 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' 'Br' 'Br' -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting tetragonal _symmetry_space_group_name_H-M P4(3)2(1)2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-y+1/2, x+1/2, z+3/4' 'y+1/2, -x+1/2, z+1/4' '-x+1/2, y+1/2, -z+3/4' 'x+1/2, -y+1/2, -z+1/4' 'y, x, -z' '-y, -x, -z+1/2' _cell_length_a 17.865(3) _cell_length_b 17.865(3) _cell_length_c 17.263(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5509.6(16) _cell_formula_units_Z 4 _cell_measurement_temperature 120(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 0.50 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.339 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2512 _exptl_absorpt_coefficient_mu 1.621 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details 'SADABS (Sheldrick)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Siemens SMART CCD' _diffrn_measurement_method 'omega scan, frame data integration' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 58853 _diffrn_reflns_av_R_equivalents 0.0519 _diffrn_reflns_av_sigmaI/netI 0.0287 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.61 _diffrn_reflns_theta_max 26.40 _reflns_number_total 5656 _reflns_number_gt 5070 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART Siemens' _computing_cell_refinement 'SAINT Siemens' _computing_data_reduction 'SAINT Siemens' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Sheldrick)' _computing_publication_material 'XCIF (Sheldrick)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.002(9) _refine_ls_number_reflns 5656 _refine_ls_number_parameters 334 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0507 _refine_ls_R_factor_gt 0.0426 _refine_ls_wR_factor_ref 0.1350 _refine_ls_wR_factor_gt 0.1276 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.074 _refine_ls_shift/su_max 0.443 _refine_ls_shift/su_mean 0.015 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 Br1 Br 0.24369(2) 0.41458(2) 0.03436(2) 0.04166(14) Uani 1 1 d . . . O1 O 0.21275(16) 0.27222(17) -0.40011(14) 0.0407(7) Uani 1 1 d . . . O2 O 0.12020(18) 0.35059(17) -0.37233(16) 0.0447(7) Uani 1 1 d . . . O3 O -0.01803(12) 0.20314(13) 0.04321(13) 0.0239(5) Uani 1 1 d . . . O4 O 0.08940(13) 0.12342(12) -0.09089(12) 0.0234(5) Uani 1 1 d . . . N1 N 0.6814(2) 0.8275(2) 0.0442(2) 0.0448(9) Uani 1 1 d . . . HN1A H 0.634(2) 0.868(2) 0.022(2) 0.023(10) Uiso 1 1 d . . . HN1B H 0.707(3) 0.794(3) 0.074(3) 0.042(12) Uiso 1 1 d . . . C1 C 0.07569(18) 0.21269(18) 0.17930(19) 0.0239(6) Uani 1 1 d . . . H1A H 0.0329 0.1800 0.1723 0.029 Uiso 1 1 calc . . . H1B H 0.0642 0.2473 0.2209 0.029 Uiso 1 1 calc . . . C2 C 0.08964(17) 0.25612(16) 0.10533(17) 0.0202(6) Uani 1 1 d . . . C3 C 0.15017(19) 0.30518(18) 0.10254(18) 0.0238(7) Uani 1 1 d . . . H3 H 0.1804 0.3121 0.1458 0.029 Uiso 1 1 calc . . . C4 C 0.16455(19) 0.34324(18) 0.0348(2) 0.0263(7) Uani 1 1 d . . . C5 C 0.12343(19) 0.33233(18) -0.0325(2) 0.0251(6) Uani 1 1 d . . . H5 H 0.1360 0.3572 -0.0780 0.030 Uiso 1 1 calc . . . C6 C 0.06226(18) 0.28280(18) -0.03015(19) 0.0228(6) Uani 1 1 d . . . C7 C 0.04579(16) 0.24774(17) 0.03878(19) 0.0221(6) Uani 1 1 d . . . C8 C 0.01980(18) 0.26722(19) -0.10448(19) 0.0241(7) Uani 1 1 d . . . H8A H -0.0201 0.2317 -0.0943 0.029 Uiso 1 1 calc . . . H8B H -0.0026 0.3132 -0.1233 0.029 Uiso 1 1 calc . . . C9 C 0.07183(17) 0.23586(18) -0.16548(18) 0.0224(6) Uani 1 1 d . . . C10 C 0.09065(18) 0.27701(18) -0.23195(18) 0.0251(7) Uani 1 1 d . . . H10 H 0.0663 0.3221 -0.2416 0.030 Uiso 1 1 calc . . . C11 C 0.14477(18) 0.25204(19) -0.28355(18) 0.0249(6) Uani 1 1 d . . . C12 C 0.18376(19) 0.18667(19) -0.26620(18) 0.0251(7) Uani 1 1 d . . . H12 H 0.2224 0.1712 -0.2985 0.030 Uiso 1 1 calc . . . C13 C 0.16588(18) 0.14416(18) -0.20147(18) 0.0229(7) Uani 1 1 d . . . C14 C 0.10785(17) 0.16689(17) -0.15437(17) 0.0200(6) Uani 1 1 d . . . C15 C 0.1607(2) 0.2958(2) -0.3565(2) 0.0344(9) Uani 1 1 d . . . C16 C -0.08315(18) 0.24972(19) 0.05853(19) 0.0294(7) Uani 1 1 d . . . H16A H -0.0933 0.2815 0.0143 0.035 Uiso 1 1 calc . . . H16B H -0.0739 0.2814 0.1031 0.035 Uiso 1 1 calc . . . C17 C -0.14936(19) 0.1991(2) 0.0740(2) 0.0328(8) Uani 1 1 d . . . H17A H -0.1369 0.1655 0.1161 0.039 Uiso 1 1 calc . . . H17B H -0.1914 0.2295 0.0904 0.039 Uiso 1 1 calc . . . C18 C -0.1725(2) 0.1534(2) 0.0045(2) 0.0369(9) Uani 1 1 d . . . H18A H -0.2139 0.1219 0.0182 0.055 Uiso 1 1 calc . . . H18B H -0.1312 0.1230 -0.0120 0.055 Uiso 1 1 calc . . . H18C H -0.1870 0.1863 -0.0368 0.055 Uiso 1 1 calc . . . C19 C 0.01979(18) 0.0846(2) -0.09725(19) 0.0274(7) Uani 1 1 d . . . H19A H -0.0145 0.1143 -0.1281 0.033 Uiso 1 1 calc . . . H19B H -0.0018 0.0790 -0.0460 0.033 Uiso 1 1 calc . . . C20 C 0.0279(2) 0.0071(2) -0.1343(2) 0.0339(8) Uani 1 1 d . . . H20A H 0.0470 0.0125 -0.1866 0.041 Uiso 1 1 calc . . . H20B H 0.0637 -0.0222 -0.1049 0.041 Uiso 1 1 calc . . . C21 C -0.0460(3) -0.0337(3) -0.1367(3) 0.0523(12) Uani 1 1 d . . . H21A H -0.0395 -0.0812 -0.1617 0.078 Uiso 1 1 calc . . . H21B H -0.0817 -0.0044 -0.1651 0.078 Uiso 1 1 calc . . . H21C H -0.0638 -0.0413 -0.0848 0.078 Uiso 1 1 calc . . . C22 C 0.6043(3) 0.8048(4) 0.0645(3) 0.0638(15) Uani 1 1 d . . . H22A H 0.5959 0.8139 0.1192 0.077 Uiso 1 1 calc . . . H22B H 0.5691 0.8353 0.0356 0.077 Uiso 1 1 calc . . . C23 C 0.5905(3) 0.7262(4) 0.0477(3) 0.0706(17) Uani 1 1 d . . . H23A H 0.5402 0.7135 0.0621 0.106 Uiso 1 1 calc . . . H23B H 0.6250 0.6958 0.0766 0.106 Uiso 1 1 calc . . . H23C H 0.5973 0.7173 -0.0067 0.106 Uiso 1 1 calc . . . C24 C 0.6972(3) 0.9085(3) 0.0581(3) 0.0535(12) Uani 1 1 d . . . H24A H 0.6895 0.9201 0.1125 0.064 Uiso 1 1 calc . . . H24B H 0.6629 0.9389 0.0279 0.064 Uiso 1 1 calc . . . C25 C 0.7761(3) 0.9268(3) 0.0359(3) 0.0594(13) Uani 1 1 d . . . H25A H 0.7853 0.9791 0.0446 0.089 Uiso 1 1 calc . . . H25B H 0.7836 0.9155 -0.0179 0.089 Uiso 1 1 calc . . . H25C H 0.8100 0.8976 0.0667 0.089 Uiso 1 1 calc . . . Cl1 Cl -0.08319(19) 0.57934(15) -0.25182(16) 0.0603(9) Uani 0.494(4) 1 d P A 1 Cl2 Cl 0.03671(18) 0.47423(17) -0.2229(3) 0.1046(18) Uani 0.494(4) 1 d P A 1 C26U C -0.0161(19) 0.5244(8) -0.1866(10) 0.203(15) Uani 0.494(4) 1 d P A 1 H26A H 0.0122 0.5603 -0.1563 0.244 Uiso 0.49 1 calc P A 1 H26B H -0.0460 0.4954 -0.1507 0.244 Uiso 0.49 1 calc P A 1 NU N -0.0275(8) 0.5920(6) -0.2711(8) 0.093(4) Uani 0.506(4) 1 d P A 2 C27U C -0.0273(6) 0.4693(5) -0.1637(6) 0.050(2) Uani 0.506(4) 1 d P A 2 H27A H 0.0244 0.4629 -0.1499 0.075 Uiso 0.51 1 calc P A 2 H27B H -0.0446 0.4257 -0.1908 0.075 Uiso 0.51 1 calc P A 2 H27C H -0.0566 0.4763 -0.1177 0.075 Uiso 0.51 1 calc P A 2 C28U C -0.0354 0.5389 -0.2167 0.050 Uani 0.51 1 d P A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.0478(3) 0.0400(2) 0.0372(2) 0.01369(17) -0.01075(18) -0.02223(18) O1 0.0419(15) 0.0544(18) 0.0259(13) 0.0047(12) 0.0055(11) -0.0044(13) O2 0.0589(19) 0.0446(17) 0.0306(14) 0.0148(13) 0.0007(13) 0.0029(14) O3 0.0174(10) 0.0275(12) 0.0268(11) -0.0009(9) 0.0048(9) -0.0005(8) O4 0.0246(11) 0.0265(11) 0.0190(10) 0.0016(8) 0.0016(9) -0.0002(9) N1 0.043(2) 0.051(2) 0.040(2) -0.0001(18) -0.0034(16) -0.0027(17) C1 0.0236(16) 0.0267(16) 0.0214(15) -0.0024(13) 0.0063(13) -0.0002(13) C2 0.0238(15) 0.0173(14) 0.0194(13) -0.0027(11) 0.0008(11) 0.0060(11) C3 0.0265(17) 0.0238(16) 0.0210(15) 0.0000(12) -0.0020(12) 0.0032(12) C4 0.0302(17) 0.0201(15) 0.0287(17) 0.0032(14) 0.0021(14) -0.0042(13) C5 0.0273(16) 0.0241(15) 0.0238(15) 0.0018(13) 0.0010(14) -0.0004(13) C6 0.0224(15) 0.0209(15) 0.0250(15) -0.0031(13) -0.0011(13) 0.0063(11) C7 0.0164(14) 0.0196(14) 0.0303(16) -0.0022(13) 0.0045(12) 0.0030(12) C8 0.0206(15) 0.0297(17) 0.0220(15) 0.0032(13) -0.0056(12) 0.0055(13) C9 0.0205(15) 0.0272(16) 0.0196(14) -0.0011(12) -0.0037(12) -0.0013(12) C10 0.0284(16) 0.0239(15) 0.0230(15) 0.0017(12) -0.0063(13) -0.0001(13) C11 0.0279(15) 0.0294(16) 0.0173(14) -0.0003(13) -0.0038(12) -0.0069(14) C12 0.0260(17) 0.0314(18) 0.0178(15) -0.0044(13) -0.0023(12) -0.0034(13) C13 0.0261(16) 0.0257(16) 0.0168(15) -0.0062(12) -0.0033(12) -0.0043(13) C14 0.0237(15) 0.0206(14) 0.0159(14) 0.0034(11) -0.0045(12) -0.0065(12) C15 0.040(2) 0.039(2) 0.0238(17) 0.0015(15) -0.0030(16) -0.0172(17) C16 0.0231(16) 0.0345(19) 0.0305(16) -0.0051(14) 0.0040(13) 0.0052(14) C17 0.0176(16) 0.044(2) 0.0364(19) -0.0005(17) 0.0066(15) 0.0007(14) C18 0.0280(18) 0.042(2) 0.041(2) -0.0058(17) 0.0023(16) -0.0052(16) C19 0.0250(16) 0.0283(17) 0.0289(17) 0.0033(14) 0.0022(13) -0.0066(14) C20 0.040(2) 0.034(2) 0.0282(18) -0.0055(15) 0.0029(15) -0.0087(16) C21 0.052(3) 0.047(3) 0.057(3) -0.006(2) 0.005(2) -0.024(2) C22 0.044(3) 0.090(4) 0.057(3) 0.026(3) 0.001(2) -0.007(3) C23 0.049(3) 0.091(4) 0.072(4) 0.044(3) -0.020(3) -0.026(3) C24 0.055(3) 0.065(3) 0.040(2) 0.000(2) -0.006(2) 0.004(2) C25 0.071(3) 0.049(3) 0.058(3) -0.003(2) 0.000(3) -0.021(2) Cl1 0.076(2) 0.0465(14) 0.0586(14) -0.0045(11) -0.0101(14) 0.0116(13) Cl2 0.0545(17) 0.0526(18) 0.207(5) 0.044(2) 0.020(2) 0.0108(13) C26U 0.45(4) 0.056(9) 0.100(11) -0.014(8) -0.187(19) 0.060(16) NU 0.089(9) 0.073(7) 0.117(10) 0.043(7) -0.021(7) -0.017(6) C27U 0.060(6) 0.036(5) 0.054(5) 0.010(4) 0.008(4) -0.003(4) C28U 0.050 0.050 0.050 0.000 0.000 0.000 _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 Br1 C4 1.904(3) . ? O1 C15 1.268(5) . ? O2 C15 1.247(5) . ? O3 C7 1.393(4) . ? O3 C16 1.455(4) . ? O4 C14 1.383(4) . ? O4 C19 1.429(4) . ? N1 C22 1.478(6) . ? N1 C24 1.495(7) . ? C1 C2 1.515(4) . ? C1 C13 1.530(5) 7 ? C2 C3 1.393(5) . ? C2 C7 1.398(4) . ? C3 C4 1.376(5) . ? C4 C5 1.388(5) . ? C5 C6 1.407(5) . ? C6 C7 1.377(5) . ? C6 C8 1.516(4) . ? C8 C9 1.512(5) . ? C9 C14 1.403(4) . ? C9 C10 1.404(5) . ? C10 C11 1.388(5) . ? C11 C12 1.392(5) . ? C11 C15 1.510(5) . ? C12 C13 1.388(5) . ? C13 C14 1.379(5) . ? C13 C1 1.530(5) 7 ? C16 C17 1.512(5) . ? C17 C18 1.508(6) . ? C19 C20 1.532(5) . ? C20 C21 1.508(5) . ? C22 C23 1.456(9) . ? C24 C25 1.498(7) . ? Cl1 C26U 1.915(15) . ? Cl2 C26U 1.44(3) . ? NU C28U 1.342(11) . ? C27U C28U 1.550(9) . ? 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 C7 O3 C16 109.7(2) . . ? C14 O4 C19 114.8(2) . . ? C22 N1 C24 113.7(4) . . ? C2 C1 C13 111.1(2) . 7 ? C3 C2 C7 118.3(3) . . ? C3 C2 C1 118.6(3) . . ? C7 C2 C1 123.1(3) . . ? C4 C3 C2 119.0(3) . . ? C3 C4 C5 122.9(3) . . ? C3 C4 Br1 118.2(3) . . ? C5 C4 Br1 118.9(2) . . ? C4 C5 C6 118.4(3) . . ? C7 C6 C5 118.5(3) . . ? C7 C6 C8 122.7(3) . . ? C5 C6 C8 118.7(3) . . ? C6 C7 O3 118.9(3) . . ? C6 C7 C2 122.8(3) . . ? O3 C7 C2 118.3(3) . . ? C9 C8 C6 110.5(3) . . ? C14 C9 C10 117.5(3) . . ? C14 C9 C8 120.8(3) . . ? C10 C9 C8 121.5(3) . . ? C11 C10 C9 121.5(3) . . ? C10 C11 C12 118.7(3) . . ? C10 C11 C15 120.0(3) . . ? C12 C11 C15 121.3(3) . . ? C13 C12 C11 121.1(3) . . ? C14 C13 C12 119.1(3) . . ? C14 C13 C1 119.9(3) . 7 ? C12 C13 C1 120.9(3) . 7 ? C13 C14 O4 118.8(3) . . ? C13 C14 C9 121.5(3) . . ? O4 C14 C9 119.5(3) . . ? O2 C15 O1 123.8(3) . . ? O2 C15 C11 118.6(3) . . ? O1 C15 C11 117.5(4) . . ? O3 C16 C17 108.4(3) . . ? C18 C17 C16 113.4(3) . . ? O4 C19 C20 112.9(3) . . ? C21 C20 C19 111.4(3) . . ? C23 C22 N1 112.0(5) . . ? N1 C24 C25 110.4(4) . . ? Cl2 C26U Cl1 118.2(10) . . ? NU C28U C27U 165.9(7) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.40 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.647 _refine_diff_density_min -0.825 _refine_diff_density_rms 0.068 data_4(Et2NH)2,II _audit_creation_method SHELXL-97 _journal_name_full ; Chemistry, A European Journal ; _publ_section_title ; A Closer Look at the Conformational Behaviour of Calix[4]arene Dicarboxylic Acids and their (Supramolecular) Interactions with Aliphatic Amines e.g. (-)-Ephedrine ; _publ_contact_author_name ; Mikkel J\/orgensen ; _publ_contact_author_address ; Condensed Matter Physics and Chemistry Department Ris\/o National Laboratory DK-4000 Roskilde Denmark ; _publ_contact_author_email 'mikkel.joergensen@risoe.dk' loop_ _publ_author_name _publ_author_address 'Krebs, Frederik C.' ; Department of Chemistry Technical University of Denmark DK-2800 Lyngby Denmark ; 'Sommer-Larsen, Peter' ; Condensed Matter Physics and Chemistry Department Ris\/o National Laboratory DK-4000 Roskilde Denmark ; 'J\/orgensen, Mikkel' ; Condensed Matter Physics and Chemistry Department Ris\/o National Laboratory DK-4000 Roskilde Denmark ; _chemical_name_systematic ; 11,23-dibromo- 25,26,27,28-tetrapropoxycalix[4]arene- 5,17-dicarboxylic acid- bis-diethylamine salt ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C51.50 H70.50 Br2 Cl N2.50 O8' _chemical_formula_weight 1047.87 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' 'Br' 'Br' -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 17.394(6) _cell_length_b 23.820(6) _cell_length_c 27.882(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 11552(6) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.205 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 4384 _exptl_absorpt_coefficient_mu 1.497 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details 'SADABS (Sheldrick)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Siemens SMART CCD' _diffrn_measurement_method 'omega scan, frame data integration' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 41459 _diffrn_reflns_av_R_equivalents 0.2705 _diffrn_reflns_av_sigmaI/netI 0.2966 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.46 _diffrn_reflns_theta_max 26.40 _reflns_number_total 11780 _reflns_number_gt 3936 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART Siemens' _computing_cell_refinement 'SAINT Siemens' _computing_data_reduction 'SAINT Siemens' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Sheldrick)' _computing_publication_material 'XCIF (Sheldrick)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1205P)^2^+171.6719P] 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 11780 _refine_ls_number_parameters 584 _refine_ls_number_restraints 53 _refine_ls_R_factor_all 0.3482 _refine_ls_R_factor_gt 0.1662 _refine_ls_wR_factor_ref 0.4240 _refine_ls_wR_factor_gt 0.3302 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 2.349 _refine_ls_shift/su_max 4.021 _refine_ls_shift/su_mean 0.016 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 Br1 Br 0.6027(3) 0.72571(16) -0.22153(16) 0.0646(15) Uani 1 1 d . . . Br2 Br 0.3074(4) 0.76155(19) -0.1578(2) 0.107(3) Uani 1 1 d . . . O1 O 0.6253(12) 0.7221(10) 0.0045(8) 0.038(6) Uani 1 1 d . . . O2 O 0.5032(12) 0.7289(9) 0.0275(8) 0.035(6) Uani 1 1 d . . . O3 O 0.4100(14) 0.6352(13) -0.4183(9) 0.061(9) Uani 1 1 d . . . O4 O 0.2852(14) 0.6382(10) -0.4006(8) 0.044(7) Uani 1 1 d . . . O5 O 0.5811(12) 0.4768(9) -0.1885(8) 0.030(5) Uani 1 1 d . . . O6 O 0.4724(11) 0.5070(9) -0.0952(7) 0.030(5) Uani 1 1 d . . . O7 O 0.2814(12) 0.5124(10) -0.1346(8) 0.040(6) Uani 1 1 d . . . O8 O 0.4003(11) 0.5043(9) -0.2191(7) 0.028(5) Uani 1 1 d . . . N1 N 0.5494(18) 0.8141(14) 0.0797(15) 0.065(11) Uani 1 1 d . . . H1A H 0.5356 0.7852 0.0608 0.078 Uiso 1 1 calc . . . H1B H 0.5069 0.8347 0.0850 0.078 Uiso 1 1 calc . . . N2 N 0.7712(15) 0.7195(11) -0.0334(10) 0.034(7) Uani 1 1 d . . . H2A H 0.7781 0.6900 -0.0531 0.041 Uiso 1 1 calc . . . H2B H 0.7222 0.7185 -0.0229 0.041 Uiso 1 1 calc . . . C1 C 0.5309(17) 0.5198(13) -0.2799(11) 0.027(8) Uani 1 1 d . . . H1A H 0.5646 0.5234 -0.3074 0.032 Uiso 1 1 calc . . . H1B H 0.5299 0.4806 -0.2702 0.032 Uiso 1 1 calc . . . C2 C 0.5607(17) 0.5560(13) -0.2387(11) 0.026(7) Uani 1 1 d U . . C3 C 0.5637(17) 0.6139(13) -0.2461(11) 0.026(7) Uani 1 1 d . . . H3 H 0.5470 0.6293 -0.2749 0.032 Uiso 1 1 calc . . . C4 C 0.592(2) 0.6477(13) -0.2101(12) 0.033(8) Uani 1 1 d . . . C5 C 0.6116(19) 0.6254(14) -0.1661(12) 0.033(8) Uani 1 1 d . . . H5 H 0.6290 0.6492 -0.1420 0.039 Uiso 1 1 calc . . . C6 C 0.6061(17) 0.5691(13) -0.1574(11) 0.025(7) Uani 1 1 d . . . C7 C 0.5830(17) 0.5338(12) -0.1953(11) 0.023(7) Uani 1 1 d . . . C8 C 0.6263(18) 0.5465(13) -0.1082(11) 0.028(8) Uani 1 1 d . . . H8A H 0.6790 0.5559 -0.1001 0.034 Uiso 1 1 calc . . . H8B H 0.6208 0.5059 -0.1075 0.034 Uiso 1 1 calc . . . C9 C 0.5707(18) 0.5737(13) -0.0730(11) 0.026(8) Uani 1 1 d . . . C10 C 0.5903(17) 0.6212(13) -0.0476(11) 0.025(7) Uani 1 1 d . . . H10 H 0.6414 0.6326 -0.0468 0.030 Uiso 1 1 calc . . . C11 C 0.5358(18) 0.6523(12) -0.0233(11) 0.023(7) Uani 1 1 d U . . C12 C 0.4597(17) 0.6349(12) -0.0247(11) 0.023(7) Uani 1 1 d . . . H12 H 0.4227 0.6557 -0.0085 0.027 Uiso 1 1 calc . . . C13 C 0.4372(17) 0.5872(13) -0.0496(11) 0.024(7) Uani 1 1 d . . . C14 C 0.4934(16) 0.5566(12) -0.0713(10) 0.019(7) Uani 1 1 d U . . C15 C 0.3514(17) 0.5752(14) -0.0570(11) 0.027(8) Uani 1 1 d . . . H15A H 0.3430 0.5350 -0.0573 0.032 Uiso 1 1 calc . . . H15B H 0.3224 0.5908 -0.0304 0.032 Uiso 1 1 calc . . . C16 C 0.3221(17) 0.6007(13) -0.1040(11) 0.026(8) Uani 1 1 d . . . C17 C 0.330(2) 0.6574(16) -0.1096(13) 0.044(10) Uani 1 1 d . . . H17 H 0.3511 0.6794 -0.0854 0.053 Uiso 1 1 calc . . . C18 C 0.304(2) 0.6817(14) -0.1524(14) 0.039(9) Uani 1 1 d . . . C19 C 0.286(2) 0.6502(17) -0.1915(13) 0.047(11) Uani 1 1 d . . . H19 H 0.2775 0.6671 -0.2212 0.057 Uiso 1 1 calc . . . C20 C 0.2787(17) 0.5940(15) -0.1862(12) 0.032(8) Uani 1 1 d . . . C21 C 0.2942(17) 0.5701(13) -0.1416(11) 0.025(7) Uani 1 1 d U . . C22 C 0.2569(16) 0.5573(15) -0.2293(12) 0.034(9) Uani 1 1 d . . . H22 H 0.2122 0.5361 -0.2315 0.041 Uiso 1 1 calc . . . C23 C 0.3195(18) 0.5604(13) -0.2682(10) 0.025(7) Uani 1 1 d . . . C24 C 0.3083(17) 0.5897(14) -0.3106(11) 0.029(8) Uani 1 1 d . . . H24 H 0.2612 0.6070 -0.3162 0.035 Uiso 1 1 calc . . . C25 C 0.3667(17) 0.5937(13) -0.3449(11) 0.024(7) Uani 1 1 d . . . C26 C 0.4377(16) 0.5690(14) -0.3344(13) 0.032(8) Uani 1 1 d . . . H26 H 0.4779 0.5731 -0.3560 0.038 Uiso 1 1 calc . . . C27 C 0.4499(17) 0.5390(13) -0.2931(10) 0.023(7) Uani 1 1 d . . . C28 C 0.3900(17) 0.5338(12) -0.2615(10) 0.022(7) Uani 1 1 d . . . C29 C 0.557(2) 0.7034(14) 0.0048(13) 0.034(9) Uani 1 1 d . . . C30 C 0.354(2) 0.6253(16) -0.3918(14) 0.044(10) Uani 1 1 d . . . C31 C 0.6541(19) 0.4498(14) -0.1987(12) 0.032(8) Uani 1 1 d U . . H31A H 0.6941 0.4666 -0.1792 0.038 Uiso 1 1 calc . . . H31B H 0.6674 0.4554 -0.2321 0.038 Uiso 1 1 calc . . . C32 C 0.649(2) 0.3879(15) -0.1882(14) 0.048(11) Uani 1 1 d . . . H32A H 0.7006 0.3719 -0.1905 0.057 Uiso 1 1 calc . . . H32B H 0.6319 0.3828 -0.1555 0.057 Uiso 1 1 calc . . . C33 C 0.597(3) 0.3562(19) -0.221(2) 0.095(19) Uani 1 1 d . . . H33A H 0.5982 0.3171 -0.2129 0.143 Uiso 1 1 calc . . . H33B H 0.6139 0.3611 -0.2535 0.143 Uiso 1 1 calc . . . H33C H 0.5457 0.3703 -0.2176 0.143 Uiso 1 1 calc . . . C34 C 0.493(2) 0.4571(14) -0.0664(11) 0.031(8) Uani 1 1 d . . . H34A H 0.4648 0.4575 -0.0363 0.038 Uiso 1 1 calc . . . H34B H 0.5473 0.4570 -0.0595 0.038 Uiso 1 1 calc . . . C35 C 0.471(2) 0.4060(14) -0.0950(13) 0.038(9) Uani 1 1 d . . . H35A H 0.4960 0.3735 -0.0807 0.046 Uiso 1 1 calc . . . H35B H 0.4915 0.4101 -0.1273 0.046 Uiso 1 1 calc . . . C36 C 0.386(2) 0.3956(16) -0.0978(13) 0.047(10) Uani 1 1 d . . . H36A H 0.3764 0.3625 -0.1164 0.071 Uiso 1 1 calc . . . H36B H 0.3613 0.4272 -0.1126 0.071 Uiso 1 1 calc . . . H36C H 0.3658 0.3905 -0.0660 0.071 Uiso 1 1 calc . . . C37 C 0.200(4) 0.493(3) -0.1238(18) 0.116(15) Uani 1 1 d U . . H37A H 0.1635 0.5140 -0.1428 0.139 Uiso 1 1 calc . . . H37B H 0.1946 0.4534 -0.1320 0.139 Uiso 1 1 calc . . . C38 C 0.185(3) 0.500(3) -0.078(3) 0.15(2) Uani 1 1 d U . . H38A H 0.1886 0.5391 -0.0694 0.176 Uiso 1 1 calc . . . H38B H 0.2204 0.4783 -0.0585 0.176 Uiso 1 1 calc . . . C39 C 0.093(4) 0.475(3) -0.073(2) 0.13(2) Uani 1 1 d U . . H39A H 0.0801 0.4704 -0.0398 0.191 Uiso 1 1 calc . . . H39B H 0.0882 0.4399 -0.0894 0.191 Uiso 1 1 calc . . . H39C H 0.0577 0.5018 -0.0872 0.191 Uiso 1 1 calc . . . C40 C 0.4034(18) 0.4445(14) -0.2239(13) 0.036(9) Uani 1 1 d . . . H40A H 0.4281 0.4293 -0.1955 0.043 Uiso 1 1 calc . . . H40B H 0.4358 0.4355 -0.2512 0.043 Uiso 1 1 calc . . . C41 C 0.3281(19) 0.4157(16) -0.2303(13) 0.043(10) Uani 1 1 d . . . H41A H 0.3018 0.4319 -0.2576 0.051 Uiso 1 1 calc . . . H41B H 0.2966 0.4223 -0.2021 0.051 Uiso 1 1 calc . . . C42 C 0.336(2) 0.3535(16) -0.2379(17) 0.061(13) Uani 1 1 d . . . H42A H 0.2862 0.3372 -0.2422 0.092 Uiso 1 1 calc . . . H42B H 0.3605 0.3369 -0.2104 0.092 Uiso 1 1 calc . . . H42C H 0.3669 0.3467 -0.2659 0.092 Uiso 1 1 calc . . . C43 C 0.603(3) 0.849(3) 0.053(3) 0.14(4) Uani 1 1 d . . . H43A H 0.6168 0.8807 0.0726 0.171 Uiso 1 1 calc . . . H43B H 0.6495 0.8270 0.0474 0.171 Uiso 1 1 calc . . . C44 C 0.575(7) 0.868(4) 0.008(4) 0.22(7) Uani 1 1 d . . . H44A H 0.6145 0.8892 -0.0074 0.336 Uiso 1 1 calc . . . H44B H 0.5310 0.8916 0.0137 0.336 Uiso 1 1 calc . . . H44C H 0.5607 0.8366 -0.0111 0.336 Uiso 1 1 calc . . . C45 C 0.575(4) 0.789(3) 0.128(3) 0.13(3) Uani 1 1 d . . . H45A H 0.6182 0.7639 0.1239 0.156 Uiso 1 1 calc . . . H45B H 0.5913 0.8192 0.1499 0.156 Uiso 1 1 calc . . . C46 C 0.506(5) 0.758(3) 0.149(2) 0.13(3) Uani 1 1 d . . . H46A H 0.5207 0.7412 0.1791 0.192 Uiso 1 1 calc . . . H46B H 0.4903 0.7295 0.1271 0.192 Uiso 1 1 calc . . . H46C H 0.4650 0.7841 0.1544 0.192 Uiso 1 1 calc . . . C47 C 0.823(2) 0.7133(16) 0.0085(13) 0.043(10) Uani 1 1 d . . . H47A H 0.8123 0.7423 0.0319 0.052 Uiso 1 1 calc . . . H47B H 0.8763 0.7177 -0.0018 0.052 Uiso 1 1 calc . . . C48 C 0.813(3) 0.656(2) 0.0314(15) 0.066(13) Uani 1 1 d . . . H48A H 0.8453 0.6530 0.0592 0.100 Uiso 1 1 calc . . . H48B H 0.8267 0.6272 0.0088 0.100 Uiso 1 1 calc . . . H48C H 0.7602 0.6511 0.0408 0.100 Uiso 1 1 calc . . . C49 C 0.783(2) 0.7718(16) -0.0612(14) 0.054(11) Uani 1 1 d . . . H49A H 0.7749 0.8040 -0.0404 0.064 Uiso 1 1 calc . . . H49B H 0.8349 0.7731 -0.0732 0.064 Uiso 1 1 calc . . . C50 C 0.729(3) 0.774(2) -0.1009(19) 0.089(17) Uani 1 1 d . . . H50A H 0.7360 0.8093 -0.1177 0.134 Uiso 1 1 calc . . . H50B H 0.6777 0.7719 -0.0891 0.134 Uiso 1 1 calc . . . H50C H 0.7392 0.7438 -0.1225 0.134 Uiso 1 1 calc . . . N3 N 0.974(4) 0.363(2) -0.142(3) 0.05(2) Uiso 0.40(3) 1 d PD A 1 C51 C 0.998(4) 0.259(2) -0.106(2) 0.020(18) Uiso 0.40(3) 1 d PD A 1 H51A H 1.0259 0.2628 -0.0767 0.030 Uiso 0.40 1 calc P A 1 H51B H 1.0282 0.2372 -0.1285 0.030 Uiso 0.40 1 calc P A 1 H51C H 0.9500 0.2412 -0.1007 0.030 Uiso 0.40 1 calc P A 1 C52 C 0.985(5) 0.316(2) -0.127(2) 0.04(2) Uiso 0.40(3) 1 d PD A 1 C53 C 0.841(4) 0.460(3) -0.103(2) 0.07(2) Uiso 0.60(3) 1 d PD A 2 H53A H 0.8796 0.4321 -0.1115 0.080 Uiso 0.60 1 calc P A 2 H53B H 0.8248 0.4795 -0.1317 0.080 Uiso 0.60 1 calc P A 2 Cl1 Cl 0.7546(18) 0.4258(13) -0.0701(11) 0.130(13) Uiso 0.60(3) 1 d PD A 2 Cl2 Cl 0.876(5) 0.507(4) -0.059(4) 0.57(8) Uiso 0.60(3) 1 d PD A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.103(4) 0.032(2) 0.058(3) 0.014(2) -0.024(3) -0.014(2) Br2 0.206(7) 0.037(3) 0.077(4) -0.005(3) -0.066(4) 0.026(4) O1 0.027(13) 0.042(14) 0.046(15) -0.001(12) 0.004(11) 0.002(12) O2 0.026(13) 0.030(13) 0.050(16) -0.012(12) 0.001(12) 0.001(11) O3 0.031(15) 0.10(2) 0.049(18) 0.040(17) -0.006(14) -0.023(15) O4 0.037(15) 0.058(17) 0.039(15) 0.025(13) -0.006(12) -0.007(13) O5 0.029(13) 0.027(12) 0.034(13) -0.004(10) 0.002(10) 0.009(10) O6 0.024(12) 0.038(14) 0.029(13) 0.004(11) 0.005(10) 0.000(11) O7 0.028(13) 0.053(16) 0.038(14) -0.001(12) 0.014(11) -0.014(12) O8 0.023(12) 0.040(13) 0.022(12) 0.003(11) -0.008(10) 0.000(11) N1 0.03(2) 0.05(2) 0.11(3) -0.05(2) 0.00(2) 0.013(17) N2 0.026(15) 0.035(17) 0.040(17) -0.014(14) 0.014(13) -0.001(13) C1 0.025(18) 0.034(18) 0.021(17) 0.000(16) 0.015(15) 0.003(15) C2 0.026(8) 0.026(8) 0.026(8) 0.000(2) 0.000(2) 0.000(2) C3 0.018(16) 0.037(19) 0.024(18) 0.008(16) 0.010(14) 0.001(15) C4 0.04(2) 0.020(16) 0.04(2) 0.004(15) -0.004(18) -0.018(16) C5 0.03(2) 0.030(19) 0.03(2) 0.005(16) -0.004(17) 0.004(16) C6 0.018(17) 0.025(17) 0.031(19) 0.002(15) -0.009(15) 0.000(15) C7 0.029(18) 0.018(16) 0.024(18) 0.001(14) 0.005(15) 0.005(14) C8 0.030(19) 0.036(19) 0.020(18) 0.013(15) -0.007(15) -0.002(16) C9 0.04(2) 0.019(17) 0.019(17) 0.004(14) 0.002(15) 0.000(15) C10 0.026(18) 0.029(18) 0.019(17) 0.010(14) -0.003(15) -0.010(15) C11 0.023(7) 0.023(7) 0.023(7) 0.000(2) 0.000(2) 0.000(2) C12 0.022(17) 0.024(17) 0.022(18) 0.003(14) -0.002(14) 0.009(14) C13 0.021(17) 0.029(18) 0.023(18) 0.004(15) -0.009(14) 0.001(14) C14 0.019(7) 0.019(7) 0.019(7) 0.000(2) 0.000(2) 0.000(2) C15 0.016(16) 0.04(2) 0.021(18) -0.008(16) 0.006(14) -0.002(15) C16 0.020(17) 0.028(18) 0.029(19) 0.005(15) -0.003(15) 0.010(15) C17 0.05(3) 0.04(2) 0.04(2) -0.033(19) -0.016(19) 0.011(19) C18 0.04(2) 0.027(19) 0.05(2) 0.000(18) -0.007(19) 0.006(17) C19 0.06(3) 0.05(3) 0.03(2) -0.010(19) -0.02(2) 0.02(2) C20 0.012(16) 0.05(2) 0.03(2) -0.007(18) -0.007(15) 0.014(16) C21 0.025(8) 0.025(8) 0.025(8) 0.000(2) 0.000(2) 0.000(2) C22 0.007(15) 0.07(2) 0.03(2) -0.015(18) -0.001(14) -0.008(16) C23 0.032(19) 0.035(19) 0.010(16) -0.007(14) 0.002(15) -0.008(16) C24 0.021(17) 0.04(2) 0.026(19) -0.020(16) -0.014(15) 0.016(16) C25 0.024(18) 0.028(18) 0.018(17) -0.010(14) -0.001(15) -0.004(15) C26 0.009(16) 0.04(2) 0.05(2) 0.002(18) 0.004(15) -0.010(15) C27 0.022(17) 0.033(18) 0.015(17) -0.005(14) -0.003(14) 0.012(15) C28 0.020(17) 0.031(17) 0.014(16) 0.000(13) 0.000(14) -0.004(15) C29 0.03(2) 0.03(2) 0.04(2) 0.009(17) -0.007(18) -0.004(17) C30 0.03(2) 0.05(3) 0.05(3) 0.01(2) -0.01(2) 0.00(2) C31 0.032(8) 0.032(8) 0.032(9) 0.000(2) 0.001(2) 0.000(2) C32 0.04(2) 0.03(2) 0.07(3) 0.02(2) 0.04(2) 0.024(19) C33 0.07(3) 0.05(3) 0.17(6) -0.04(3) 0.00(4) -0.02(3) C34 0.04(2) 0.030(19) 0.021(18) 0.006(15) 0.001(16) -0.003(17) C35 0.04(2) 0.026(19) 0.05(2) 0.008(17) 0.002(18) -0.003(17) C36 0.04(2) 0.05(2) 0.05(2) 0.02(2) -0.020(19) -0.02(2) C37 0.116(15) 0.181(15) 0.052(15) 0.000(3) 0.000(3) 0.111(3) C38 0.05(2) 0.11(2) 0.28(2) 0.000(3) 0.000(3) 0.000(3) C39 0.13(2) 0.13(2) 0.13(2) 0.000(3) 0.000(3) 0.000(3) C40 0.019(17) 0.05(2) 0.04(2) 0.017(18) 0.012(17) 0.001(16) C41 0.023(19) 0.06(3) 0.05(2) 0.01(2) -0.008(17) -0.002(18) C42 0.06(3) 0.03(2) 0.10(4) 0.01(2) 0.02(2) 0.01(2) C43 0.06(4) 0.10(5) 0.27(10) -0.12(6) 0.11(5) -0.06(4) C44 0.33(15) 0.09(6) 0.25(12) 0.03(7) 0.20(11) -0.04(7) C45 0.10(4) 0.14(6) 0.15(6) -0.12(5) -0.11(5) 0.09(4) C46 0.16(7) 0.13(6) 0.09(5) -0.01(4) -0.07(5) 0.00(5) C47 0.03(2) 0.06(3) 0.04(2) -0.02(2) -0.002(18) -0.014(19) C48 0.07(3) 0.09(3) 0.04(3) 0.01(2) 0.00(2) -0.01(3) C49 0.07(3) 0.04(2) 0.05(2) 0.01(2) 0.00(2) -0.02(2) C50 0.11(4) 0.07(3) 0.09(4) 0.03(3) -0.01(3) -0.01(3) _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 Br1 C4 1.89(3) . ? Br2 C18 1.91(3) . ? O1 C29 1.27(4) . ? O2 C29 1.28(4) . ? O3 C30 1.24(4) . ? O4 C30 1.27(4) . ? O5 C7 1.37(3) . ? O5 C31 1.45(4) . ? O6 C14 1.40(3) . ? O6 C34 1.48(4) . ? O7 C21 1.41(4) . ? O7 C37 1.52(7) . ? O8 C28 1.39(3) . ? O8 C40 1.43(4) . ? N1 C43 1.45(7) . ? N1 C45 1.55(8) . ? N2 C49 1.48(4) . ? N2 C47 1.49(4) . ? C1 C27 1.53(4) . ? C1 C2 1.53(4) . ? C2 C7 1.38(4) . ? C2 C3 1.39(4) . ? C3 C4 1.38(4) . ? C4 C5 1.38(4) . ? C5 C6 1.37(4) . ? C6 C7 1.41(4) . ? C6 C8 1.52(4) . ? C8 C9 1.52(4) . ? C9 C10 1.38(4) . ? C9 C14 1.41(4) . ? C10 C11 1.38(4) . ? C11 C12 1.39(4) . ? C11 C29 1.49(4) . ? C12 C13 1.39(4) . ? C13 C14 1.36(4) . ? C13 C15 1.53(4) . ? C15 C16 1.53(4) . ? C16 C21 1.37(4) . ? C16 C17 1.37(5) . ? C17 C18 1.40(5) . ? C18 C19 1.36(5) . ? C19 C20 1.35(5) . ? C20 C21 1.39(4) . ? C20 C22 1.53(4) . ? C22 C23 1.54(4) . ? C23 C24 1.39(4) . ? C23 C28 1.39(4) . ? C24 C25 1.40(4) . ? C25 C26 1.40(4) . ? C25 C30 1.52(5) . ? C26 C27 1.37(4) . ? C27 C28 1.37(4) . ? C31 C32 1.51(5) . ? C32 C33 1.49(6) . ? C34 C35 1.50(5) . ? C35 C36 1.51(5) . ? C37 C38 1.31(9) . ? C38 C39 1.72(8) . ? C40 C41 1.49(5) . ? C41 C42 1.50(5) . ? C43 C44 1.41(13) . ? C45 C46 1.52(10) . ? C47 C48 1.52(6) . ? C49 C50 1.45(6) . ? N3 C52 1.200(2) . ? C51 C52 1.500(2) . ? C53 Cl2 1.760(3) . ? C53 Cl1 1.94(8) . ? 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 C7 O5 C31 113(2) . . ? C14 O6 C34 111(2) . . ? C21 O7 C37 118(3) . . ? C28 O8 C40 116(2) . . ? C43 N1 C45 119(5) . . ? C49 N2 C47 114(3) . . ? C27 C1 C2 109(2) . . ? C7 C2 C3 120(3) . . ? C7 C2 C1 123(3) . . ? C3 C2 C1 117(3) . . ? C4 C3 C2 119(3) . . ? C3 C4 C5 121(3) . . ? C3 C4 Br1 119(2) . . ? C5 C4 Br1 120(2) . . ? C6 C5 C4 121(3) . . ? C5 C6 C7 118(3) . . ? C5 C6 C8 120(3) . . ? C7 C6 C8 122(3) . . ? O5 C7 C2 120(3) . . ? O5 C7 C6 120(3) . . ? C2 C7 C6 121(3) . . ? C6 C8 C9 107(2) . . ? C10 C9 C14 117(3) . . ? C10 C9 C8 122(3) . . ? C14 C9 C8 120(3) . . ? C9 C10 C11 122(3) . . ? C10 C11 C12 119(3) . . ? C10 C11 C29 122(3) . . ? C12 C11 C29 120(3) . . ? C13 C12 C11 122(3) . . ? C14 C13 C12 117(3) . . ? C14 C13 C15 123(3) . . ? C12 C13 C15 120(3) . . ? C13 C14 O6 118(3) . . ? C13 C14 C9 123(3) . . ? O6 C14 C9 119(3) . . ? C16 C15 C13 111(3) . . ? C21 C16 C17 118(3) . . ? C21 C16 C15 124(3) . . ? C17 C16 C15 117(3) . . ? C16 C17 C18 118(3) . . ? C19 C18 C17 122(3) . . ? C19 C18 Br2 119(3) . . ? C17 C18 Br2 118(3) . . ? C20 C19 C18 119(3) . . ? C19 C20 C21 119(3) . . ? C19 C20 C22 120(3) . . ? C21 C20 C22 121(3) . . ? C16 C21 C20 122(3) . . ? C16 C21 O7 118(3) . . ? C20 C21 O7 120(3) . . ? C20 C22 C23 111(2) . . ? C24 C23 C28 118(3) . . ? C24 C23 C22 122(3) . . ? C28 C23 C22 120(3) . . ? C23 C24 C25 121(3) . . ? C26 C25 C24 118(3) . . ? C26 C25 C30 121(3) . . ? C24 C25 C30 121(3) . . ? C27 C26 C25 122(3) . . ? C28 C27 C26 118(3) . . ? C28 C27 C1 121(3) . . ? C26 C27 C1 120(3) . . ? C27 C28 O8 120(3) . . ? C27 C28 C23 123(3) . . ? O8 C28 C23 117(3) . . ? O1 C29 O2 121(3) . . ? O1 C29 C11 121(3) . . ? O2 C29 C11 118(3) . . ? O3 C30 O4 125(4) . . ? O3 C30 C25 120(3) . . ? O4 C30 C25 115(3) . . ? O5 C31 C32 110(3) . . ? C33 C32 C31 114(4) . . ? O6 C34 C35 108(3) . . ? C34 C35 C36 114(3) . . ? C38 C37 O7 110(6) . . ? C37 C38 C39 103(6) . . ? O8 C40 C41 116(3) . . ? C40 C41 C42 113(3) . . ? C44 C43 N1 115(7) . . ? C46 C45 N1 107(4) . . ? N2 C47 C48 110(3) . . ? C50 C49 N2 111(3) . . ? N3 C52 C51 177(6) . . ? Cl2 C53 Cl1 102(3) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 26.40 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 2.479 _refine_diff_density_min -1.829 _refine_diff_density_rms 0.140 data_4 _audit_creation_method SHELXL-97 _journal_name_full ; Chemistry, A European Journal ; _publ_section_title ; A Closer Look at the Conformational Behaviour of Calix[4]arene Dicarboxylic Acids and their (Supramolecular) Interactions with Aliphatic Amines e.g. (-)-Ephedrine ; _publ_contact_author_name ; Mikkel J\/orgensen ; _publ_contact_author_address ; Condensed Matter Physics and Chemistry Department Ris\/o National Laboratory DK-4000 Roskilde Denmark ; _publ_contact_author_email 'mikkel.joergensen@risoe.dk' loop_ _publ_author_name _publ_author_address 'Krebs, Frederik C.' ; Department of Chemistry Technical University of Denmark DK-2800 Lyngby Denmark ; 'Sommer-Larsen, Peter' ; Condensed Matter Physics and Chemistry Department Ris\/o National Laboratory DK-4000 Roskilde Denmark ; 'J\/orgensen, Mikkel' ; Condensed Matter Physics and Chemistry Department Ris\/o National Laboratory DK-4000 Roskilde Denmark ; _chemical_name_systematic ; 11,23-dibromo- 25,26,27,28-tetrapropoxycalix[4]arene- 5,17-dicarboxylic acid ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C42 H46 Br2 O8' _chemical_formula_weight 838.61 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' 'Br' 'Br' -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/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 12.505(3) _cell_length_b 24.822(5) _cell_length_c 12.722(3) _cell_angle_alpha 90.00 _cell_angle_beta 94.80(3) _cell_angle_gamma 90.00 _cell_volume 3935.0(14) _cell_formula_units_Z 4 _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 0.50 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.416 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1728 _exptl_absorpt_coefficient_mu 2.111 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details 'SADABS (Sheldrick)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Siemens SMART CCD' _diffrn_measurement_method 'omega scan, frame data integration' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 40482 _diffrn_reflns_av_R_equivalents 0.0546 _diffrn_reflns_av_sigmaI/netI 0.0417 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.64 _diffrn_reflns_theta_max 26.35 _reflns_number_total 8012 _reflns_number_gt 6260 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART Siemens' _computing_cell_refinement 'SAINT Siemens' _computing_data_reduction 'SAINT Siemens' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Sheldrick)' _computing_publication_material 'XCIF (Sheldrick)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0444P)^2^+9.7415P] 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 8012 _refine_ls_number_parameters 498 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0691 _refine_ls_R_factor_gt 0.0470 _refine_ls_wR_factor_ref 0.1157 _refine_ls_wR_factor_gt 0.1040 _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_restrained_S_all 1.018 _refine_ls_shift/su_max 0.066 _refine_ls_shift/su_mean 0.004 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 Br1 Br 0.45400(3) 0.101578(16) 0.34463(3) 0.03103(11) Uani 1 1 d . A . Br2 Br -0.00785(3) 0.040906(18) -0.63505(3) 0.03891(13) Uani 1 1 d . A . O1 O 0.21653(18) -0.00746(10) 0.01128(17) 0.0227(5) Uani 1 1 d . . . O2 O 0.12499(18) -0.01594(10) -0.14638(18) 0.0235(5) Uani 1 1 d . . . O3 O -0.0682(2) 0.06442(11) -0.0934(2) 0.0330(6) Uani 1 1 d . . . O4 O 0.0246(2) 0.07382(11) 0.0636(2) 0.0306(6) Uani 1 1 d . . . O5 O 0.44489(18) 0.18362(9) -0.10215(17) 0.0190(5) Uani 1 1 d . . . O6 O 0.55888(17) 0.08712(9) -0.27843(17) 0.0167(5) Uani 1 1 d . . . O7 O 0.31413(18) 0.15677(10) -0.33813(17) 0.0213(5) Uani 1 1 d . . . O8 O 0.24509(18) 0.25437(9) -0.19634(18) 0.0205(5) Uani 1 1 d . . . C1 C 0.2928(3) 0.22669(14) 0.0220(3) 0.0206(7) Uani 1 1 d . A . H1A H 0.3263 0.2548 -0.0168 0.025 Uiso 1 1 calc . . . H1B H 0.2579 0.2435 0.0789 0.025 Uiso 1 1 calc . . . C2 C 0.3776(3) 0.18768(13) 0.0672(3) 0.0180(7) Uani 1 1 d . . . C3 C 0.3802(3) 0.16834(14) 0.1711(3) 0.0204(7) Uani 1 1 d . A . H3 H 0.3349 0.1830 0.2180 0.024 Uiso 1 1 calc . . . C4 C 0.4504(3) 0.12750(14) 0.2033(2) 0.0197(7) Uani 1 1 d . . . C5 C 0.5154(3) 0.10275(13) 0.1349(2) 0.0186(7) Uani 1 1 d . A . H5 H 0.5591 0.0740 0.1575 0.022 Uiso 1 1 calc . . . C6 C 0.5144(2) 0.12150(13) 0.0312(2) 0.0161(6) Uani 1 1 d . . . C7 C 0.4494(3) 0.16545(13) 0.0007(2) 0.0165(7) Uani 1 1 d . A . C8 C 0.5659(3) 0.08928(13) -0.0516(2) 0.0158(6) Uani 1 1 d . A . H8A H 0.6137 0.0624 -0.0184 0.019 Uiso 1 1 calc . . . H8B H 0.6074 0.1128 -0.0935 0.019 Uiso 1 1 calc . . . C9 C 0.4768(2) 0.06205(13) -0.1218(2) 0.0143(6) Uani 1 1 d . . . C10 C 0.3897(2) 0.03968(13) -0.0766(2) 0.0149(6) Uani 1 1 d . A . H10 H 0.3900 0.0381 -0.0035 0.018 Uiso 1 1 calc . . . C11 C 0.3015(2) 0.01952(12) -0.1392(2) 0.0140(6) Uani 1 1 d . . . C12 C 0.3000(3) 0.02219(13) -0.2487(2) 0.0158(6) Uani 1 1 d . A . H12 H 0.2410 0.0090 -0.2902 0.019 Uiso 1 1 calc . . . C13 C 0.3863(2) 0.04452(13) -0.2966(2) 0.0148(6) Uani 1 1 d . . . C14 C 0.4747(2) 0.06295(13) -0.2323(2) 0.0144(6) Uani 1 1 d . A . C15 C 0.3767(3) 0.05336(13) -0.4156(2) 0.0175(7) Uani 1 1 d . A . H15A H 0.4344 0.0764 -0.4350 0.021 Uiso 1 1 calc . . . H15B H 0.3821 0.0191 -0.4516 0.021 Uiso 1 1 calc . . . C16 C 0.2692(3) 0.07940(14) -0.4482(2) 0.0179(7) Uani 1 1 d . . . C17 C 0.1933(3) 0.05335(14) -0.5167(3) 0.0223(7) Uani 1 1 d . A . H17 H 0.2116 0.0221 -0.5511 0.027 Uiso 1 1 calc . . . C18 C 0.0909(3) 0.07405(15) -0.5333(3) 0.0242(8) Uani 1 1 d . . . C19 C 0.0587(3) 0.11854(15) -0.4774(3) 0.0235(8) Uani 1 1 d . A . H19 H -0.0125 0.1298 -0.4848 0.028 Uiso 1 1 calc . . . C20 C 0.1340(3) 0.14624(14) -0.4098(2) 0.0193(7) Uani 1 1 d . . . C21 C 0.2400(3) 0.12764(13) -0.4016(2) 0.0172(7) Uani 1 1 d . A . C22 C 0.1032(3) 0.19386(14) -0.3450(3) 0.0226(7) Uani 1 1 d . A . H22A H 0.0287 0.2030 -0.3641 0.027 Uiso 1 1 calc . . . H22B H 0.1468 0.2247 -0.3607 0.027 Uiso 1 1 calc . . . C23 C 0.1186(3) 0.18176(13) -0.2266(3) 0.0177(7) Uani 1 1 d . . . C24 C 0.0612(3) 0.13976(13) -0.1858(3) 0.0190(7) Uani 1 1 d . A . H24 H 0.0128 0.1202 -0.2302 0.023 Uiso 1 1 calc . . . C25 C 0.0756(3) 0.12674(13) -0.0787(3) 0.0178(7) Uani 1 1 d . . . C26 C 0.1514(3) 0.15463(13) -0.0127(3) 0.0192(7) Uani 1 1 d . A . H26 H 0.1633 0.1448 0.0578 0.023 Uiso 1 1 calc . . . C27 C 0.2094(3) 0.19709(13) -0.0514(3) 0.0192(7) Uani 1 1 d . . . C28 C 0.1904(3) 0.21101(13) -0.1582(3) 0.0186(7) Uani 1 1 d . A . C29 C 0.2078(3) -0.00291(12) -0.0894(2) 0.0154(6) Uani 1 1 d . A . C30 C 0.0060(3) 0.08519(14) -0.0346(3) 0.0202(7) Uani 1 1 d . A . C31 C 0.5399(4) 0.2083(2) -0.1372(4) 0.0209(16) Uani 0.753(14) 1 d P A 1 H31A H 0.5588 0.1909 -0.2013 0.025 Uiso 0.75 1 calc P A 1 H31B H 0.5993 0.2038 -0.0837 0.025 Uiso 0.75 1 calc P A 1 C32 C 0.5201(4) 0.2674(2) -0.1574(4) 0.0243(16) Uani 0.753(14) 1 d P A 1 H32A H 0.5166 0.2860 -0.0907 0.029 Uiso 0.75 1 calc P A 1 H32B H 0.4517 0.2721 -0.1983 0.029 Uiso 0.75 1 calc P A 1 C31U C 0.4958(15) 0.2377(8) -0.1141(14) 0.031(5) Uani 0.247(14) 1 d P A 2 H31C H 0.4529 0.2591 -0.1656 0.038 Uiso 0.25 1 calc P A 2 H31D H 0.5005 0.2568 -0.0473 0.038 Uiso 0.25 1 calc P A 2 C32U C 0.606(3) 0.2292(12) -0.150(4) 0.126(16) Uani 0.247(14) 1 d P A 2 H32C H 0.6101 0.1986 -0.1966 0.151 Uiso 0.25 1 calc P A 2 H32D H 0.6613 0.2265 -0.0915 0.151 Uiso 0.25 1 calc P A 2 C33 C 0.6087(4) 0.2919(2) -0.2167(4) 0.0550(13) Uani 1 1 d . . . H33A H 0.5883 0.3276 -0.2394 0.083 Uiso 1 1 calc . B 1 H33B H 0.6200 0.2701 -0.2770 0.083 Uiso 1 1 calc . C 1 H33C H 0.6738 0.2935 -0.1710 0.083 Uiso 1 1 calc . D 1 C34 C 0.6519(3) 0.05283(14) -0.2837(3) 0.0229(7) Uani 1 1 d . G . H34A H 0.6355 0.0237 -0.3332 0.028 Uiso 1 1 calc . . . H34B H 0.6722 0.0374 -0.2149 0.028 Uiso 1 1 calc . . . C35 C 0.7425(3) 0.08634(17) -0.3191(4) 0.0383(10) Uani 1 1 d D . . H35A H 0.7600 0.1140 -0.2666 0.046 Uiso 1 1 calc . E 1 H35B H 0.8051 0.0635 -0.3218 0.046 Uiso 1 1 calc . F 1 C36 C 0.7199(4) 0.1125(2) -0.4228(5) 0.0488(18) Uani 0.851(11) 1 d P G 1 H36A H 0.7812 0.1332 -0.4392 0.073 Uiso 0.85 1 calc P G 1 H36B H 0.6589 0.1358 -0.4208 0.073 Uiso 0.85 1 calc P G 1 H36C H 0.7050 0.0854 -0.4760 0.073 Uiso 0.85 1 calc P G 1 C36U C 0.768(2) 0.1429(4) -0.293(2) 0.038(9) Uani 0.149(11) 1 d PD G 2 H36D H 0.8281 0.1542 -0.3291 0.057 Uiso 0.15 1 calc P G 2 H36E H 0.7845 0.1463 -0.2182 0.057 Uiso 0.15 1 calc P G 2 H36F H 0.7068 0.1650 -0.3143 0.057 Uiso 0.15 1 calc P G 2 C37 C 0.3899(3) 0.18743(16) -0.3945(3) 0.0315(9) Uani 1 1 d . . . H37A H 0.4442 0.1629 -0.4165 0.038 Uiso 1 1 calc . . . H37B H 0.4256 0.2132 -0.3461 0.038 Uiso 1 1 calc . . . C38 C 0.3431(3) 0.21721(17) -0.4892(3) 0.0377(10) Uani 1 1 d . . . H38A H 0.2855 0.2403 -0.4691 0.045 Uiso 1 1 calc . . . H38B H 0.3127 0.1916 -0.5410 0.045 Uiso 1 1 calc . . . C39 C 0.4270(4) 0.2515(2) -0.5382(4) 0.0580(14) Uani 1 1 d . . . H39A H 0.3959 0.2672 -0.6027 0.087 Uiso 1 1 calc . . . H39B H 0.4868 0.2293 -0.5530 0.087 Uiso 1 1 calc . . . H39C H 0.4511 0.2795 -0.4900 0.087 Uiso 1 1 calc . . . C40 C 0.1876(3) 0.30461(14) -0.1900(3) 0.0244(8) Uani 1 1 d . . . H40A H 0.1660 0.3096 -0.1192 0.029 Uiso 1 1 calc . . . H40B H 0.1235 0.3041 -0.2386 0.029 Uiso 1 1 calc . . . C41 C 0.2599(3) 0.35009(14) -0.2178(3) 0.0299(8) Uani 1 1 d . . . H41A H 0.3225 0.3507 -0.1673 0.036 Uiso 1 1 calc . . . H41B H 0.2221 0.3839 -0.2115 0.036 Uiso 1 1 calc . . . C42 C 0.2968(3) 0.34590(17) -0.3282(4) 0.0402(10) Uani 1 1 d . . . H42A H 0.3399 0.3767 -0.3419 0.060 Uiso 1 1 calc . . . H42B H 0.2353 0.3447 -0.3787 0.060 Uiso 1 1 calc . . . H42C H 0.3384 0.3137 -0.3337 0.060 Uiso 1 1 calc . . . H43 H 0.1610 -0.0227 0.0364 0.050 Uiso 1 1 d . . . H44 H -0.0235 0.0472 0.0873 0.050 Uiso 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 Br1 0.0455(2) 0.0333(2) 0.01502(17) 0.00242(15) 0.00709(14) -0.00586(18) Br2 0.0342(2) 0.0397(2) 0.0395(2) 0.00066(18) -0.01706(17) -0.01068(19) O1 0.0178(12) 0.0326(14) 0.0182(12) 0.0054(10) 0.0047(9) -0.0061(10) O2 0.0168(12) 0.0297(14) 0.0235(12) 0.0042(10) -0.0018(10) -0.0086(10) O3 0.0315(15) 0.0337(15) 0.0356(15) -0.0039(12) 0.0129(12) -0.0170(12) O4 0.0266(14) 0.0328(15) 0.0338(14) 0.0169(12) 0.0114(11) -0.0011(12) O5 0.0169(12) 0.0229(12) 0.0171(11) 0.0052(9) 0.0013(9) -0.0024(10) O6 0.0134(11) 0.0211(12) 0.0163(11) 0.0024(9) 0.0055(9) -0.0004(9) O7 0.0177(12) 0.0270(13) 0.0189(11) -0.0048(10) -0.0010(9) -0.0035(10) O8 0.0174(12) 0.0143(11) 0.0306(13) 0.0060(10) 0.0064(10) -0.0002(9) C1 0.0213(17) 0.0182(17) 0.0230(17) -0.0028(13) 0.0051(13) -0.0015(14) C2 0.0180(16) 0.0156(16) 0.0205(16) -0.0028(13) 0.0011(13) -0.0050(13) C3 0.0213(17) 0.0219(18) 0.0184(16) -0.0033(13) 0.0041(13) -0.0058(14) C4 0.0260(18) 0.0228(18) 0.0103(14) 0.0017(13) 0.0016(13) -0.0105(15) C5 0.0193(17) 0.0182(17) 0.0177(16) -0.0003(13) -0.0015(12) -0.0046(14) C6 0.0138(15) 0.0181(16) 0.0160(15) -0.0022(12) -0.0010(12) -0.0058(13) C7 0.0164(16) 0.0191(17) 0.0135(15) -0.0014(12) -0.0013(12) -0.0064(13) C8 0.0145(15) 0.0182(17) 0.0147(15) 0.0002(12) 0.0010(12) -0.0023(13) C9 0.0145(16) 0.0138(15) 0.0144(15) 0.0012(12) -0.0003(12) 0.0004(12) C10 0.0158(15) 0.0163(16) 0.0125(14) 0.0019(12) 0.0006(12) 0.0017(13) C11 0.0150(16) 0.0120(15) 0.0154(15) 0.0008(12) 0.0030(12) 0.0004(12) C12 0.0172(16) 0.0144(16) 0.0154(15) -0.0017(12) -0.0014(12) 0.0009(13) C13 0.0156(16) 0.0155(16) 0.0135(15) -0.0021(12) 0.0018(12) 0.0016(13) C14 0.0146(16) 0.0135(15) 0.0158(15) 0.0018(12) 0.0045(12) 0.0011(12) C15 0.0185(16) 0.0227(18) 0.0114(15) 0.0002(12) 0.0028(12) -0.0010(13) C16 0.0190(17) 0.0256(18) 0.0092(14) 0.0048(12) 0.0013(12) -0.0035(14) C17 0.0276(19) 0.0230(18) 0.0159(16) 0.0006(13) -0.0004(14) -0.0026(15) C18 0.0226(18) 0.0278(19) 0.0209(17) 0.0069(14) -0.0064(14) -0.0085(15) C19 0.0124(16) 0.031(2) 0.0263(18) 0.0126(15) -0.0024(13) -0.0038(14) C20 0.0199(17) 0.0210(17) 0.0171(16) 0.0091(13) 0.0015(13) -0.0007(14) C21 0.0189(16) 0.0203(17) 0.0122(15) 0.0045(12) -0.0010(12) -0.0057(14) C22 0.0192(17) 0.0234(18) 0.0253(18) 0.0091(14) 0.0037(14) 0.0019(14) C23 0.0141(16) 0.0184(17) 0.0212(16) 0.0032(13) 0.0050(12) 0.0050(13) C24 0.0142(16) 0.0189(17) 0.0243(17) -0.0002(13) 0.0038(13) -0.0007(13) C25 0.0165(16) 0.0155(16) 0.0225(16) 0.0037(13) 0.0081(13) 0.0014(13) C26 0.0201(17) 0.0170(17) 0.0216(16) 0.0029(13) 0.0080(13) 0.0042(14) C27 0.0152(16) 0.0144(16) 0.0290(18) 0.0009(13) 0.0077(13) 0.0027(13) C28 0.0159(16) 0.0139(16) 0.0272(17) 0.0024(13) 0.0080(13) 0.0037(13) C29 0.0160(16) 0.0119(15) 0.0184(16) 0.0009(12) 0.0020(12) 0.0017(13) C30 0.0171(17) 0.0188(17) 0.0257(18) 0.0003(13) 0.0078(14) 0.0031(14) C31 0.018(3) 0.024(3) 0.021(2) 0.0037(19) 0.0017(19) -0.002(2) C32 0.029(3) 0.021(3) 0.024(3) 0.000(2) 0.009(2) -0.005(2) C31U 0.029(9) 0.032(12) 0.032(9) 0.003(8) 0.000(7) 0.003(9) C32U 0.08(2) 0.060(19) 0.23(5) 0.08(2) 0.00(2) -0.015(17) C33 0.059(3) 0.055(3) 0.051(3) 0.009(2) 0.011(2) -0.027(3) C34 0.0170(17) 0.0256(19) 0.0271(18) -0.0022(14) 0.0075(14) 0.0033(14) C35 0.020(2) 0.038(2) 0.059(3) 0.002(2) 0.0135(19) 0.0001(17) C36 0.035(3) 0.056(4) 0.058(4) 0.021(3) 0.023(3) -0.001(3) C36U 0.037(16) 0.014(13) 0.07(2) 0.015(12) 0.043(15) 0.010(11) C37 0.0186(18) 0.033(2) 0.043(2) -0.0100(17) 0.0059(16) -0.0122(16) C38 0.038(2) 0.035(2) 0.043(2) 0.0011(18) 0.0156(19) -0.0117(19) C39 0.059(3) 0.045(3) 0.076(4) -0.002(3) 0.042(3) -0.020(3) C40 0.0207(18) 0.0167(17) 0.036(2) 0.0054(15) 0.0051(15) 0.0051(14) C41 0.029(2) 0.0154(18) 0.046(2) 0.0021(16) 0.0044(17) 0.0002(15) C42 0.038(2) 0.026(2) 0.057(3) 0.0176(19) 0.012(2) 0.0031(18) _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 Br1 C4 1.907(3) . ? Br2 C18 1.900(3) . ? O1 C29 1.281(4) . ? O2 C29 1.255(4) . ? O3 C30 1.254(4) . ? O4 C30 1.283(4) . ? O5 C7 1.380(4) . ? O5 C31 1.440(5) . ? O5 C31U 1.50(2) . ? O6 C14 1.384(4) . ? O6 C34 1.447(4) . ? O7 C21 1.382(4) . ? O7 C37 1.451(4) . ? O8 C28 1.385(4) . ? O8 C40 1.445(4) . ? C1 C2 1.514(5) . ? C1 C27 1.529(5) . ? C2 C7 1.398(5) . ? C2 C3 1.405(5) . ? C3 C4 1.381(5) . ? C4 C5 1.383(5) . ? C5 C6 1.398(4) . ? C6 C7 1.396(5) . ? C6 C8 1.509(4) . ? C8 C9 1.526(4) . ? C9 C10 1.390(4) . ? C9 C14 1.404(4) . ? C10 C11 1.397(4) . ? C11 C12 1.393(4) . ? C11 C29 1.487(4) . ? C12 C13 1.399(4) . ? C13 C14 1.396(4) . ? C13 C15 1.524(4) . ? C15 C16 1.517(5) . ? C16 C17 1.393(5) . ? C16 C21 1.398(5) . ? C17 C18 1.380(5) . ? C18 C19 1.391(5) . ? C19 C20 1.402(5) . ? C20 C21 1.399(5) . ? C20 C22 1.509(5) . ? C22 C23 1.532(4) . ? C23 C24 1.391(5) . ? C23 C28 1.400(5) . ? C24 C25 1.397(5) . ? C25 C26 1.396(5) . ? C25 C30 1.489(5) . ? C26 C27 1.393(5) . ? C27 C28 1.402(5) . ? C31 C32 1.506(8) . ? C32 C33 1.519(7) . ? C31U C32U 1.50(4) . ? C32U C33 1.77(3) . ? C34 C35 1.504(5) . ? C35 C36U 1.4699(11) . ? C35 C36 1.477(7) . ? C37 C38 1.490(6) . ? C38 C39 1.524(6) . ? C40 C41 1.507(5) . ? C41 C42 1.518(6) . ? 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 C7 O5 C31 117.6(3) . . ? C7 O5 C31U 113.9(7) . . ? C31 O5 C31U 38.7(7) . . ? C14 O6 C34 114.0(2) . . ? C21 O7 C37 114.8(3) . . ? C28 O8 C40 112.8(2) . . ? C2 C1 C27 110.2(3) . . ? C7 C2 C3 118.0(3) . . ? C7 C2 C1 119.2(3) . . ? C3 C2 C1 122.4(3) . . ? C4 C3 C2 119.6(3) . . ? C3 C4 C5 122.2(3) . . ? C3 C4 Br1 119.4(2) . . ? C5 C4 Br1 118.4(3) . . ? C4 C5 C6 119.1(3) . . ? C7 C6 C5 118.8(3) . . ? C7 C6 C8 119.5(3) . . ? C5 C6 C8 120.8(3) . . ? O5 C7 C6 119.7(3) . . ? O5 C7 C2 117.9(3) . . ? C6 C7 C2 121.9(3) . . ? C6 C8 C9 108.1(3) . . ? C10 C9 C14 118.1(3) . . ? C10 C9 C8 119.6(3) . . ? C14 C9 C8 122.0(3) . . ? C9 C10 C11 121.1(3) . . ? C12 C11 C10 119.8(3) . . ? C12 C11 C29 119.9(3) . . ? C10 C11 C29 120.3(3) . . ? C11 C12 C13 120.6(3) . . ? C14 C13 C12 118.5(3) . . ? C14 C13 C15 121.9(3) . . ? C12 C13 C15 119.4(3) . . ? O6 C14 C13 119.1(3) . . ? O6 C14 C9 118.7(3) . . ? C13 C14 C9 122.0(3) . . ? C16 C15 C13 109.2(3) . . ? C17 C16 C21 118.3(3) . . ? C17 C16 C15 121.0(3) . . ? C21 C16 C15 120.4(3) . . ? C18 C17 C16 119.9(3) . . ? C17 C18 C19 121.5(3) . . ? C17 C18 Br2 119.0(3) . . ? C19 C18 Br2 119.5(3) . . ? C18 C19 C20 119.7(3) . . ? C21 C20 C19 117.9(3) . . ? C21 C20 C22 120.1(3) . . ? C19 C20 C22 122.0(3) . . ? O7 C21 C20 117.1(3) . . ? O7 C21 C16 120.6(3) . . ? C20 C21 C16 122.1(3) . . ? C20 C22 C23 111.5(3) . . ? C24 C23 C28 118.7(3) . . ? C24 C23 C22 119.2(3) . . ? C28 C23 C22 122.1(3) . . ? C23 C24 C25 120.6(3) . . ? C24 C25 C26 119.8(3) . . ? C24 C25 C30 119.7(3) . . ? C26 C25 C30 120.4(3) . . ? C27 C26 C25 120.7(3) . . ? C26 C27 C28 118.5(3) . . ? C26 C27 C1 119.8(3) . . ? C28 C27 C1 121.7(3) . . ? O8 C28 C23 119.7(3) . . ? O8 C28 C27 118.8(3) . . ? C23 C28 C27 121.5(3) . . ? O2 C29 O1 123.5(3) . . ? O2 C29 C11 119.5(3) . . ? O1 C29 C11 117.0(3) . . ? O3 C30 O4 123.8(3) . . ? O3 C30 C25 119.1(3) . . ? O4 C30 C25 117.1(3) . . ? O5 C31 C32 109.8(4) . . ? C31 C32 C33 111.0(4) . . ? C32U C31U O5 108.3(18) . . ? C31U C32U C33 94.3(18) . . ? C32 C33 C32U 50.8(12) . . ? O6 C34 C35 108.5(3) . . ? C36U C35 C36 78.7(12) . . ? C36U C35 C34 127.8(10) . . ? C36 C35 C34 114.7(4) . . ? O7 C37 C38 115.5(3) . . ? C37 C38 C39 111.7(4) . . ? O8 C40 C41 108.8(3) . . ? C40 C41 C42 113.6(3) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.35 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.643 _refine_diff_density_min -1.399 _refine_diff_density_rms 0.082 data_9 _audit_creation_method SHELXL-97 _journal_name_full ; Chemistry, A European Journal ; _publ_section_title ; A Closer Look at the Conformational Behaviour of Calix[4]arene Dicarboxylic Acids and their (Supramolecular) Interactions with Aliphatic Amines e.g. (-)-Ephedrine ; _publ_contact_author_name ; Mikkel J\/orgensen ; _publ_contact_author_address ; Condensed Matter Physics and Chemistry Department Ris\/o National Laboratory DK-4000 Roskilde Denmark ; _publ_contact_author_email 'mikkel.joergensen@risoe.dk' loop_ _publ_author_name _publ_author_address 'Krebs, Frederik C.' ; Department of Chemistry Technical University of Denmark DK-2800 Lyngby Denmark ; 'Sommer-Larsen, Peter' ; Condensed Matter Physics and Chemistry Department Ris\/o National Laboratory DK-4000 Roskilde Denmark ; 'J\/orgensen, Mikkel' ; Condensed Matter Physics and Chemistry Department Ris\/o National Laboratory DK-4000 Roskilde Denmark ; _chemical_name_systematic ; 11,23-Bis((E)-(phenylazo)- 25,26,27,28-tetrapropoxycalix[4]arene- 5,17-dicarboxylic acid ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C54 H56 N4 O8' _chemical_formula_weight 889.03 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 monoclinic _symmetry_space_group_name_H-M P2(1)/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 22.391(5) _cell_length_b 13.024(3) _cell_length_c 33.539(7) _cell_angle_alpha 90.00 _cell_angle_beta 97.64(3) _cell_angle_gamma 90.00 _cell_volume 9694(3) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.218 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3776 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details 'SADABS (Sheldrick)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Siemens SMART CCD' _diffrn_measurement_method 'omega scan, frame data integration' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 97941 _diffrn_reflns_av_R_equivalents 0.5150 _diffrn_reflns_av_sigmaI/netI 0.4603 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -41 _diffrn_reflns_limit_l_max 41 _diffrn_reflns_theta_min 1.03 _diffrn_reflns_theta_max 26.42 _reflns_number_total 19836 _reflns_number_gt 4493 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART Siemens' _computing_cell_refinement 'SAINT Siemens' _computing_data_reduction 'SAINT Siemens' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Sheldrick)' _computing_publication_material 'XCIF (Sheldrick)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^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 19836 _refine_ls_number_parameters 1189 _refine_ls_number_restraints 15 _refine_ls_R_factor_all 0.4386 _refine_ls_R_factor_gt 0.1481 _refine_ls_wR_factor_ref 0.3724 _refine_ls_wR_factor_gt 0.2584 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.071 _refine_ls_shift/su_max 1.534 _refine_ls_shift/su_mean 0.038 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 0.7646(3) 0.0181(5) 0.11267(19) 0.051(2) Uani 1 1 d . . . O2 O 0.8476(3) -0.0686(5) 0.1366(2) 0.058(2) Uani 1 1 d . . . H2 H 0.8504 -0.0183 0.1515 0.087 Uiso 1 1 calc . . . O3 O 0.9011(4) 0.1090(6) 0.0780(2) 0.067(2) Uani 1 1 d . . . O4 O 0.8177(4) 0.1876(7) 0.0476(2) 0.076(3) Uani 1 1 d . . . H4 H 0.8208 0.2166 0.0695 0.115 Uiso 1 1 calc . . . O5 O 0.8714(3) -0.2935(6) -0.0187(2) 0.059(2) Uani 1 1 d . . . O6 O 0.7408(3) -0.3906(6) 0.0070(2) 0.053(2) Uani 1 1 d . . . O7 O 0.7395(3) -0.1830(6) -0.0549(2) 0.057(2) Uani 1 1 d . . . O8 O 0.8696(3) -0.1042(6) -0.0931(2) 0.056(2) Uani 1 1 d D . . N1 N 1.0708(5) -0.2943(9) 0.1034(4) 0.108(5) Uani 1 1 d . . . N2 N 1.1147(5) -0.2785(8) 0.0867(3) 0.079(3) Uani 1 1 d . . . N3 N 0.5783(4) 0.1350(7) -0.0366(3) 0.055(3) Uani 1 1 d . . . N4 N 0.5574(4) 0.1320(7) -0.0058(4) 0.078(3) Uani 1 1 d . . . C1 C 0.9599(5) -0.1446(9) -0.0263(3) 0.061(3) Uani 1 1 d . . . H1A H 0.9973 -0.1064 -0.0253 0.073 Uiso 1 1 calc . . . H1B H 0.9536 -0.1814 -0.0517 0.073 Uiso 1 1 calc . . . C2 C 0.9652(5) -0.2210(9) 0.0081(3) 0.053(3) Uani 1 1 d . . . C3 C 1.0149(5) -0.2201(8) 0.0380(4) 0.052(3) Uani 1 1 d . . . H3 H 1.0470 -0.1764 0.0353 0.062 Uiso 1 1 calc . . . C4 C 1.0178(5) -0.2828(9) 0.0719(4) 0.057(3) Uani 1 1 d . . . C5 C 0.9653(5) -0.3418(8) 0.0767(3) 0.052(3) Uani 1 1 d . . . H5 H 0.9645 -0.3796 0.1002 0.062 Uiso 1 1 calc . . . C6 C 0.9161(5) -0.3437(8) 0.0475(3) 0.046(3) Uani 1 1 d . . . C7 C 0.9180(5) -0.2882(9) 0.0123(3) 0.050(3) Uani 1 1 d . . . C8 C 0.8573(4) -0.3918(8) 0.0547(3) 0.043(3) Uani 1 1 d . . . H8A H 0.8435 -0.4387 0.0330 0.052 Uiso 1 1 calc . . . H8B H 0.8629 -0.4304 0.0797 0.052 Uiso 1 1 calc . . . C9 C 0.8111(5) -0.3092(8) 0.0570(3) 0.042(3) Uani 1 1 d . . . C10 C 0.8226(4) -0.2271(8) 0.0823(3) 0.041(3) Uani 1 1 d . . . H10 H 0.8582 -0.2275 0.1000 0.049 Uiso 1 1 calc . . . C11 C 0.7855(4) -0.1449(8) 0.0831(3) 0.034(3) Uani 1 1 d . . . C12 C 0.7323(4) -0.1416(8) 0.0564(3) 0.039(3) Uani 1 1 d . . . H12 H 0.7070 -0.0849 0.0561 0.047 Uiso 1 1 calc . . . C13 C 0.7170(4) -0.2219(9) 0.0302(3) 0.043(3) Uani 1 1 d . . . C14 C 0.7548(5) -0.3076(9) 0.0322(3) 0.043(3) Uani 1 1 d . . . C15 C 0.6611(5) -0.2171(9) -0.0017(3) 0.054(3) Uani 1 1 d . . . H15A H 0.6619 -0.2748 -0.0199 0.065 Uiso 1 1 calc . . . H15B H 0.6253 -0.2235 0.0115 0.065 Uiso 1 1 calc . . . C16 C 0.6574(4) -0.1197(8) -0.0255(3) 0.041(3) Uani 1 1 d . . . C17 C 0.6165(5) -0.0418(10) -0.0209(3) 0.053(3) Uani 1 1 d . . . H17 H 0.5872 -0.0530 -0.0041 0.063 Uiso 1 1 calc . . . C18 C 0.6177(5) 0.0515(10) -0.0401(3) 0.055(3) Uani 1 1 d . . . C19 C 0.6613(6) 0.0662(8) -0.0650(3) 0.055(3) Uani 1 1 d . . . H19 H 0.6620 0.1279 -0.0789 0.066 Uiso 1 1 calc . . . C20 C 0.7046(5) -0.0084(9) -0.0701(3) 0.046(3) Uani 1 1 d . . . C21 C 0.7008(5) -0.1061(9) -0.0519(3) 0.041(3) Uani 1 1 d . . . C22 C 0.7632(5) 0.0181(8) -0.0880(3) 0.055(3) Uani 1 1 d . . . H22A H 0.7687 -0.0300 -0.1093 0.066 Uiso 1 1 calc . . . H22B H 0.7602 0.0866 -0.0994 0.066 Uiso 1 1 calc . . . C23 C 0.8159(5) 0.0124(8) -0.0556(3) 0.047(3) Uani 1 1 d . . . C24 C 0.8130(4) 0.0666(8) -0.0199(3) 0.048(3) Uani 1 1 d . . . H24 H 0.7806 0.1097 -0.0175 0.058 Uiso 1 1 calc . . . C25 C 0.8599(5) 0.0550(8) 0.0123(3) 0.045(3) Uani 1 1 d . . . C26 C 0.9052(5) -0.0153(8) 0.0104(3) 0.047(3) Uani 1 1 d . . . H26 H 0.9337 -0.0257 0.0328 0.056 Uiso 1 1 calc . . . C27 C 0.9089(5) -0.0712(8) -0.0244(3) 0.048(3) Uani 1 1 d . . . C28 C 0.8648(5) -0.0505(8) -0.0581(3) 0.045(3) Uani 1 1 d . . . C29 C 0.7985(4) -0.0630(9) 0.1121(3) 0.039(3) Uani 1 1 d . . . C30 C 0.8580(6) 0.1194(9) 0.0482(3) 0.052(3) Uani 1 1 d . . . C31 C 1.1679(6) -0.2976(10) 0.1142(4) 0.077(4) Uani 1 1 d . . . C32 C 1.2217(7) -0.2976(10) 0.0975(4) 0.089(4) Uani 1 1 d . . . H32 H 1.2218 -0.2818 0.0705 0.107 Uiso 1 1 calc . . . C33 C 1.2758(6) -0.3219(10) 0.1221(5) 0.085(4) Uani 1 1 d . . . H33 H 1.3118 -0.3244 0.1111 0.102 Uiso 1 1 calc . . . C34 C 1.2757(7) -0.3420(10) 0.1627(5) 0.087(5) Uani 1 1 d . . . H34 H 1.3116 -0.3546 0.1794 0.104 Uiso 1 1 calc . . . C35 C 1.2208(7) -0.3433(11) 0.1783(4) 0.094(5) Uani 1 1 d . . . H35 H 1.2199 -0.3595 0.2052 0.113 Uiso 1 1 calc . . . C36 C 1.1689(6) -0.3207(12) 0.1542(4) 0.095(5) Uani 1 1 d . . . H36 H 1.1328 -0.3210 0.1652 0.114 Uiso 1 1 calc . . . C37 C 0.5218(5) 0.2199(10) 0.0033(4) 0.067(4) Uani 1 1 d . . . C38 C 0.5010(5) 0.2925(12) -0.0260(4) 0.082(4) Uani 1 1 d . . . H38 H 0.5088 0.2818 -0.0522 0.098 Uiso 1 1 calc . . . C39 C 0.4694(6) 0.3792(11) -0.0177(5) 0.089(4) Uani 1 1 d . . . H39 H 0.4548 0.4253 -0.0379 0.107 Uiso 1 1 calc . . . C40 C 0.4602(6) 0.3950(11) 0.0227(5) 0.087(4) Uani 1 1 d . . . H40 H 0.4419 0.4553 0.0298 0.105 Uiso 1 1 calc . . . C41 C 0.4778(6) 0.3226(13) 0.0520(5) 0.088(5) Uani 1 1 d . . . H41 H 0.4689 0.3316 0.0781 0.105 Uiso 1 1 calc . . . C42 C 0.5086(6) 0.2371(12) 0.0421(4) 0.088(5) Uani 1 1 d . . . H42 H 0.5211 0.1892 0.0621 0.106 Uiso 1 1 calc . . . C43 C 0.8677(6) -0.3919(14) -0.0412(4) 0.118(6) Uani 1 1 d . . . H43A H 0.8850 -0.4461 -0.0235 0.142 Uiso 1 1 calc . . . H43B H 0.8257 -0.4087 -0.0496 0.142 Uiso 1 1 calc . . . C44 C 0.8990(11) -0.3886(16) -0.0765(5) 0.179(9) Uani 1 1 d . . . H44A H 0.8719 -0.4189 -0.0984 0.215 Uiso 1 1 calc . . . H44B H 0.9028 -0.3167 -0.0832 0.215 Uiso 1 1 calc . . . C45 C 0.949(3) -0.428(2) -0.0777(12) 0.75(7) Uani 1 1 d . . . H45A H 0.9662 -0.4022 -0.1006 1.126 Uiso 1 1 calc . . . H45B H 0.9451 -0.5015 -0.0800 1.126 Uiso 1 1 calc . . . H45C H 0.9755 -0.4117 -0.0535 1.126 Uiso 1 1 calc . . . C46 C 0.7127(6) -0.4735(11) 0.0261(4) 0.084(4) Uani 1 1 d . . . H46A H 0.6743 -0.4511 0.0334 0.101 Uiso 1 1 calc . . . H46B H 0.7382 -0.4945 0.0504 0.101 Uiso 1 1 calc . . . C47 C 0.7033(7) -0.5639(15) -0.0035(6) 0.154(7) Uani 1 1 d . . . H47A H 0.7416 -0.5764 -0.0131 0.185 Uiso 1 1 calc . . . H47B H 0.6757 -0.5404 -0.0265 0.185 Uiso 1 1 calc . . . C48 C 0.6795(9) -0.6704(19) 0.0090(9) 0.288(17) Uani 1 1 d . . . H48A H 0.6785 -0.7175 -0.0131 0.432 Uiso 1 1 calc . . . H48B H 0.6396 -0.6625 0.0160 0.432 Uiso 1 1 calc . . . H48C H 0.7057 -0.6965 0.0317 0.432 Uiso 1 1 calc . . . C49 C 0.7405(6) -0.2237(13) -0.0965(5) 0.106(5) Uani 1 1 d . . . H49A H 0.7183 -0.1778 -0.1158 0.127 Uiso 1 1 calc . . . H49B H 0.7818 -0.2272 -0.1023 0.127 Uiso 1 1 calc . . . C50 C 0.7159(7) -0.3165(14) -0.0998(5) 0.111(6) Uani 1 1 d . . . H50A H 0.6728 -0.3119 -0.0994 0.133 Uiso 1 1 calc . . . H50B H 0.7330 -0.3595 -0.0775 0.133 Uiso 1 1 calc . . . C51 C 0.7304(8) -0.3666(11) -0.1434(4) 0.120(6) Uani 1 1 d . . . H51A H 0.7127 -0.4337 -0.1468 0.180 Uiso 1 1 calc . . . H51B H 0.7732 -0.3718 -0.1432 0.180 Uiso 1 1 calc . . . H51C H 0.7137 -0.3231 -0.1652 0.180 Uiso 1 1 calc . . . C52 C 0.9041(14) -0.0261(15) -0.1232(5) 0.256(17) Uani 1 1 d . . . H52A H 0.8773 0.0069 -0.1445 0.307 Uiso 1 1 calc . . . H52B H 0.9323 0.0222 -0.1090 0.307 Uiso 1 1 calc . . . C53 C 0.9359(7) -0.1395(17) -0.1368(5) 0.246(17) Uani 1 1 d D . . H53A H 0.9062 -0.1851 -0.1512 0.296 Uiso 1 1 calc . . . H53B H 0.9575 -0.1750 -0.1139 0.296 Uiso 1 1 calc . . . C54 C 0.9738(7) -0.0992(13) -0.1614(8) 0.223(13) Uani 1 1 d . . . H54A H 0.9979 -0.1531 -0.1705 0.335 Uiso 1 1 calc . . . H54B H 0.9996 -0.0492 -0.1468 0.335 Uiso 1 1 calc . . . H54C H 0.9506 -0.0671 -0.1841 0.335 Uiso 1 1 calc . . . O1A O 0.8287(3) 0.3373(5) 0.1016(2) 0.059(2) Uani 1 1 d . . . O2A O 0.9147(3) 0.2653(6) 0.12666(19) 0.057(2) Uani 1 1 d . . . H2A H 0.8997 0.2180 0.1126 0.086 Uiso 1 1 calc . . . O3A O 0.8819(3) 0.0747(5) 0.18920(19) 0.050(2) Uani 1 1 d . . . O4A O 0.7945(3) 0.1552(5) 0.17160(19) 0.054(2) Uani 1 1 d . . . H4A H 0.7927 0.1121 0.1536 0.080 Uiso 1 1 calc . . . O5A O 0.8508(3) 0.5668(5) 0.26087(19) 0.0440(18) Uani 1 1 d . . . O6A O 0.9559(3) 0.6910(6) 0.2136(2) 0.0494(19) Uani 1 1 d . . . O7A O 0.9923(3) 0.4795(5) 0.27388(18) 0.0400(18) Uani 1 1 d . . . O8A O 0.8949(3) 0.3927(5) 0.33202(18) 0.0404(17) Uani 1 1 d . . . N1A N 0.6206(5) 0.5548(8) 0.1696(4) 0.114(5) Uani 1 1 d D . . N2A N 0.5884(5) 0.5005(8) 0.1874(3) 0.105(4) Uani 1 1 d D . . N3A N 1.1571(4) 0.2110(7) 0.2208(2) 0.047(2) Uani 1 1 d . . . N4A N 1.1613(4) 0.1273(7) 0.2370(2) 0.047(2) Uani 1 1 d . . . C1A C 0.7757(4) 0.4099(8) 0.2871(3) 0.052(3) Uani 1 1 d . . . H1A1 H 0.7422 0.3679 0.2930 0.063 Uiso 1 1 calc . . . H1A2 H 0.7908 0.4472 0.3114 0.063 Uiso 1 1 calc . . . C2A C 0.7533(4) 0.4855(8) 0.2548(3) 0.044(3) Uani 1 1 d . . . C3A C 0.6946(5) 0.4820(9) 0.2328(4) 0.064(4) Uani 1 1 d . . . H3A H 0.6644 0.4397 0.2402 0.077 Uiso 1 1 calc . . . C4A C 0.6853(5) 0.5470(11) 0.1990(4) 0.075(5) Uani 1 1 d D . . C5A C 0.7218(7) 0.6046(11) 0.1849(4) 0.077(4) Uani 1 1 d . . . H5A H 0.7107 0.6418 0.1614 0.093 Uiso 1 1 calc . . . C6A C 0.7798(5) 0.6109(8) 0.2058(3) 0.049(3) Uani 1 1 d . . . C7A C 0.7924(5) 0.5544(8) 0.2418(3) 0.046(3) Uani 1 1 d . . . C8A C 0.8294(5) 0.6703(8) 0.1887(3) 0.054(3) Uani 1 1 d . . . H8A1 H 0.8487 0.7179 0.2086 0.065 Uiso 1 1 calc . . . H8A2 H 0.8125 0.7090 0.1652 0.065 Uiso 1 1 calc . . . C9A C 0.8753(5) 0.5922(8) 0.1773(3) 0.042(3) Uani 1 1 d . . . C10A C 0.8578(5) 0.5047(9) 0.1551(3) 0.046(3) Uani 1 1 d . . . H10A H 0.8175 0.4963 0.1446 0.055 Uiso 1 1 calc . . . C11A C 0.8985(5) 0.4306(8) 0.1482(3) 0.043(3) Uani 1 1 d . . . C12A C 0.9589(4) 0.4443(8) 0.1659(3) 0.040(3) Uani 1 1 d . . . H12A H 0.9862 0.3916 0.1635 0.049 Uiso 1 1 calc . . . C13A C 0.9791(4) 0.5305(9) 0.1864(3) 0.039(3) Uani 1 1 d . . . C14A C 0.9365(5) 0.6049(9) 0.1915(3) 0.044(3) Uani 1 1 d . . . C15A C 1.0446(4) 0.5336(8) 0.2050(3) 0.041(3) Uani 1 1 d . . . H15C H 1.0698 0.5414 0.1838 0.050 Uiso 1 1 calc . . . H15D H 1.0509 0.5930 0.2225 0.050 Uiso 1 1 calc . . . C16A C 1.0631(4) 0.4397(8) 0.2286(3) 0.040(3) Uani 1 1 d . . . C17A C 1.1027(4) 0.3673(9) 0.2174(3) 0.045(3) Uani 1 1 d . . . H17A H 1.1245 0.3831 0.1965 0.054 Uiso 1 1 calc . . . C18A C 1.1116(5) 0.2747(9) 0.2354(3) 0.044(3) Uani 1 1 d . . . C19A C 1.0762(4) 0.2457(7) 0.2645(3) 0.039(3) Uani 1 1 d . . . H19A H 1.0794 0.1802 0.2756 0.046 Uiso 1 1 calc . . . C20A C 1.0360(4) 0.3160(8) 0.2767(3) 0.031(2) Uani 1 1 d . . . C21A C 1.0321(4) 0.4122(8) 0.2607(3) 0.034(3) Uani 1 1 d . . . C22A C 0.9925(4) 0.2805(7) 0.3059(3) 0.041(3) Uani 1 1 d . . . H22C H 1.0039 0.2125 0.3160 0.049 Uiso 1 1 calc . . . H22D H 0.9949 0.3271 0.3286 0.049 Uiso 1 1 calc . . . C23A C 0.9284(4) 0.2781(8) 0.2844(3) 0.036(3) Uani 1 1 d . . . C24A C 0.9160(4) 0.2164(8) 0.2513(3) 0.044(3) Uani 1 1 d . . . H24A H 0.9463 0.1753 0.2433 0.053 Uiso 1 1 calc . . . C25A C 0.8581(4) 0.2142(7) 0.2291(3) 0.039(3) Uani 1 1 d . . . C26A C 0.8134(4) 0.2805(8) 0.2405(3) 0.044(3) Uani 1 1 d . . . H26A H 0.7760 0.2849 0.2248 0.053 Uiso 1 1 calc . . . C27A C 0.8255(5) 0.3400(7) 0.2757(3) 0.040(3) Uani 1 1 d . . . C28A C 0.8834(5) 0.3346(7) 0.2975(3) 0.039(3) Uani 1 1 d . . . C29A C 0.8783(6) 0.3398(9) 0.1245(3) 0.047(3) Uani 1 1 d . . . C30A C 0.8439(5) 0.1461(8) 0.1944(3) 0.037(3) Uani 1 1 d . . . C31A C 0.5206(5) 0.5035(12) 0.1583(5) 0.105(5) Uani 1 1 d DU . . C32A C 0.4748(12) 0.4504(14) 0.1721(6) 0.204(12) Uani 1 1 d D . . H32A H 0.4842 0.4182 0.1969 0.245 Uiso 1 1 calc . . . C33A C 0.4207(6) 0.4398(19) 0.1549(8) 0.203(13) Uani 1 1 d D . . H33A H 0.3929 0.3938 0.1630 0.243 Uiso 1 1 calc . . . C34A C 0.4089(6) 0.5070(13) 0.1221(5) 0.089(5) Uani 1 1 d . . . H34A H 0.3690 0.5086 0.1100 0.107 Uiso 1 1 calc . . . C35A C 0.4467(6) 0.5697(11) 0.1056(4) 0.100(5) Uani 1 1 d D . . H35A H 0.4337 0.6105 0.0834 0.121 Uiso 1 1 calc . . . C36A C 0.5122(7) 0.5702(10) 0.1254(4) 0.122(7) Uani 1 1 d D . . H36A H 0.5425 0.6097 0.1166 0.146 Uiso 1 1 calc . . . C37A C 1.2085(5) 0.0620(10) 0.2245(3) 0.050(3) Uani 1 1 d . . . C38A C 1.2108(5) -0.0367(10) 0.2360(4) 0.072(4) Uani 1 1 d . . . H38A H 1.1828 -0.0606 0.2519 0.086 Uiso 1 1 calc . . . C39A C 1.2537(6) -0.1048(10) 0.2249(5) 0.085(4) Uani 1 1 d . . . H39A H 1.2545 -0.1734 0.2327 0.103 Uiso 1 1 calc . . . C40A C 1.2950(6) -0.0652(12) 0.2019(4) 0.073(4) Uani 1 1 d . . . H40A H 1.3238 -0.1087 0.1934 0.088 Uiso 1 1 calc . . . C41A C 1.2948(6) 0.0343(13) 0.1913(3) 0.073(4) Uani 1 1 d . . . H41A H 1.3243 0.0590 0.1767 0.088 Uiso 1 1 calc . . . C42A C 1.2507(6) 0.1008(9) 0.2020(3) 0.065(4) Uani 1 1 d . . . H42A H 1.2498 0.1694 0.1942 0.078 Uiso 1 1 calc . . . C43A C 0.8567(5) 0.6145(11) 0.3011(4) 0.073(4) Uani 1 1 d . . . H43C H 0.8206 0.6001 0.3132 0.088 Uiso 1 1 calc . . . H43D H 0.8905 0.5835 0.3179 0.088 Uiso 1 1 calc . . . C44A C 0.8653(5) 0.7214(10) 0.3002(4) 0.078(4) Uani 1 1 d . . . H44C H 0.8321 0.7535 0.2832 0.094 Uiso 1 1 calc . . . H44D H 0.9023 0.7370 0.2893 0.094 Uiso 1 1 calc . . . C45A C 0.8690(5) 0.7646(9) 0.3452(3) 0.072(4) Uani 1 1 d . . . H45D H 0.8745 0.8377 0.3451 0.108 Uiso 1 1 calc . . . H45E H 0.9024 0.7333 0.3618 0.108 Uiso 1 1 calc . . . H45F H 0.8323 0.7486 0.3558 0.108 Uiso 1 1 calc . . . C46A C 0.9621(5) 0.7774(10) 0.1882(3) 0.067(4) Uani 1 1 d . . . H46C H 0.9237 0.7934 0.1725 0.080 Uiso 1 1 calc . . . H46D H 0.9909 0.7620 0.1698 0.080 Uiso 1 1 calc . . . C47A C 0.9831(7) 0.8647(12) 0.2136(4) 0.103(5) Uani 1 1 d . . . H47C H 0.9577 0.8725 0.2347 0.124 Uiso 1 1 calc . . . H47D H 0.9798 0.9269 0.1975 0.124 Uiso 1 1 calc . . . C48A C 1.0521(7) 0.8495(11) 0.2336(6) 0.152(8) Uani 1 1 d . . . H48D H 1.0649 0.9086 0.2496 0.228 Uiso 1 1 calc . . . H48E H 1.0773 0.8415 0.2128 0.228 Uiso 1 1 calc . . . H48F H 1.0551 0.7895 0.2503 0.228 Uiso 1 1 calc . . . C49A C 1.0184(5) 0.5668(10) 0.2964(3) 0.064(4) Uani 1 1 d . . . H49C H 0.9895 0.6226 0.2941 0.077 Uiso 1 1 calc . . . H49D H 1.0536 0.5898 0.2849 0.077 Uiso 1 1 calc . . . C50A C 1.0363(5) 0.5416(9) 0.3400(4) 0.071(4) Uani 1 1 d . . . H50C H 1.0678 0.4900 0.3427 0.085 Uiso 1 1 calc . . . H50D H 1.0020 0.5142 0.3513 0.085 Uiso 1 1 calc . . . C51A C 1.0597(5) 0.6425(10) 0.3633(4) 0.080(4) Uani 1 1 d . . . H51D H 1.0701 0.6273 0.3913 0.120 Uiso 1 1 calc . . . H51E H 1.0286 0.6937 0.3600 0.120 Uiso 1 1 calc . . . H51F H 1.0946 0.6678 0.3526 0.120 Uiso 1 1 calc . . . C52A C 0.8834(5) 0.3372(8) 0.3679(3) 0.056(3) Uani 1 1 d . . . H52C H 0.8984 0.2675 0.3671 0.067 Uiso 1 1 calc . . . H52D H 0.8405 0.3345 0.3693 0.067 Uiso 1 1 calc . . . C53A C 0.9144(5) 0.3915(10) 0.4033(3) 0.062(3) Uani 1 1 d . . . H53C H 0.9051 0.3558 0.4271 0.074 Uiso 1 1 calc . . . H53D H 0.9574 0.3847 0.4027 0.074 Uiso 1 1 calc . . . C54A C 0.9017(6) 0.4991(11) 0.4083(3) 0.082(4) Uani 1 1 d . . . H54D H 0.9249 0.5240 0.4325 0.122 Uiso 1 1 calc . . . H54E H 0.8596 0.5079 0.4101 0.122 Uiso 1 1 calc . . . H54F H 0.9122 0.5369 0.3857 0.122 Uiso 1 1 calc . . . 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 0.031(4) 0.068(5) 0.052(5) 0.000(4) 0.002(4) 0.009(4) O2 0.046(5) 0.080(6) 0.050(5) -0.024(4) 0.010(4) -0.002(4) O3 0.074(6) 0.090(6) 0.036(5) -0.011(4) 0.003(4) -0.002(5) O4 0.063(6) 0.111(7) 0.057(5) -0.040(5) 0.013(5) -0.018(5) O5 0.039(5) 0.098(6) 0.042(5) -0.016(5) 0.010(4) -0.015(4) O6 0.058(5) 0.056(5) 0.047(5) -0.012(4) 0.017(4) -0.004(4) O7 0.053(5) 0.083(6) 0.040(5) -0.010(4) 0.022(4) 0.010(5) O8 0.038(5) 0.100(6) 0.033(4) -0.024(5) 0.010(4) 0.003(4) N1 0.033(7) 0.158(11) 0.145(11) 0.111(9) 0.060(8) 0.045(7) N2 0.063(8) 0.102(9) 0.068(7) 0.027(6) -0.005(7) 0.009(7) N3 0.049(7) 0.081(8) 0.039(6) 0.003(6) 0.021(5) 0.024(6) N4 0.047(7) 0.064(8) 0.113(10) -0.023(7) -0.017(7) 0.021(6) C1 0.047(8) 0.082(9) 0.056(8) -0.004(7) 0.018(6) -0.011(7) C2 0.028(7) 0.088(9) 0.042(7) -0.010(7) 0.006(6) -0.005(7) C3 0.029(7) 0.059(8) 0.070(8) 0.012(7) 0.015(6) -0.006(6) C4 0.046(8) 0.059(8) 0.069(9) 0.003(7) 0.022(7) 0.027(7) C5 0.043(8) 0.061(8) 0.057(8) -0.001(6) 0.028(7) 0.008(6) C6 0.022(7) 0.065(8) 0.054(8) -0.001(6) 0.015(6) -0.003(6) C7 0.019(7) 0.081(9) 0.054(8) -0.015(7) 0.019(6) -0.001(6) C8 0.034(7) 0.070(8) 0.025(6) 0.006(5) 0.001(5) 0.005(6) C9 0.029(7) 0.053(8) 0.051(7) 0.006(6) 0.027(6) 0.004(6) C10 0.032(7) 0.053(7) 0.041(7) -0.001(6) 0.019(5) 0.003(6) C11 0.031(6) 0.055(7) 0.021(6) -0.012(5) 0.017(5) 0.003(6) C12 0.035(7) 0.056(8) 0.028(6) 0.002(6) 0.010(5) -0.005(6) C13 0.030(7) 0.068(8) 0.034(6) -0.006(6) 0.012(5) -0.003(6) C14 0.042(8) 0.058(8) 0.035(7) -0.002(6) 0.022(6) 0.003(6) C15 0.039(7) 0.077(9) 0.048(7) -0.016(7) 0.012(6) -0.001(6) C16 0.029(7) 0.045(7) 0.047(7) 0.004(6) -0.006(6) 0.004(6) C17 0.034(7) 0.079(9) 0.042(7) -0.013(7) -0.006(6) -0.002(7) C18 0.049(8) 0.072(9) 0.042(8) 0.008(7) 0.001(6) 0.018(7) C19 0.059(9) 0.061(8) 0.041(7) 0.005(6) -0.009(6) 0.006(7) C20 0.042(8) 0.058(8) 0.036(7) -0.013(6) -0.002(5) -0.006(7) C21 0.032(7) 0.059(8) 0.033(6) -0.021(6) 0.003(5) -0.016(6) C22 0.038(7) 0.089(9) 0.036(7) -0.004(6) 0.003(6) -0.014(6) C23 0.043(8) 0.057(8) 0.046(7) 0.004(6) 0.024(6) 0.006(6) C24 0.030(7) 0.068(8) 0.049(7) -0.010(6) 0.014(6) -0.007(6) C25 0.041(7) 0.059(8) 0.039(7) -0.005(6) 0.015(6) -0.009(6) C26 0.049(8) 0.044(7) 0.048(7) 0.001(6) 0.008(6) -0.014(6) C27 0.035(7) 0.060(8) 0.052(8) -0.015(6) 0.016(6) -0.003(6) C28 0.034(7) 0.049(7) 0.054(8) -0.016(6) 0.011(6) -0.016(6) C29 0.009(6) 0.073(9) 0.037(6) 0.007(6) 0.010(5) -0.005(6) C30 0.048(8) 0.054(8) 0.054(8) -0.007(7) 0.006(7) 0.000(7) C31 0.051(10) 0.098(11) 0.076(10) 0.030(9) -0.010(8) -0.016(8) C32 0.054(10) 0.113(12) 0.097(11) 0.043(9) -0.004(9) 0.024(9) C33 0.047(9) 0.108(12) 0.101(12) 0.004(10) 0.010(9) 0.009(8) C34 0.073(11) 0.075(10) 0.098(12) -0.005(9) -0.042(10) 0.000(8) C35 0.057(10) 0.133(13) 0.091(11) 0.003(9) 0.001(9) -0.026(10) C36 0.043(9) 0.166(15) 0.072(10) 0.033(10) -0.009(8) 0.005(9) C37 0.052(9) 0.068(10) 0.081(10) 0.008(9) 0.005(8) 0.013(7) C38 0.030(8) 0.104(12) 0.112(12) -0.012(10) 0.011(8) 0.006(8) C39 0.063(10) 0.106(12) 0.095(12) -0.027(10) 0.001(9) 0.004(9) C40 0.073(11) 0.094(12) 0.103(12) -0.024(10) 0.043(9) -0.005(9) C41 0.058(10) 0.108(13) 0.100(12) -0.003(10) 0.023(9) 0.015(9) C42 0.083(11) 0.131(13) 0.052(9) -0.019(9) 0.011(8) 0.037(10) C43 0.078(11) 0.229(19) 0.047(9) -0.034(11) 0.007(8) -0.001(11) C44 0.30(3) 0.18(2) 0.084(13) -0.014(13) 0.102(16) 0.032(18) C45 1.59(16) 0.28(3) 0.59(6) 0.30(4) 0.92(9) 0.56(7) C46 0.069(10) 0.091(11) 0.091(11) -0.039(9) 0.004(8) -0.037(8) C47 0.092(14) 0.175(18) 0.193(19) -0.027(16) 0.004(13) -0.045(13) C48 0.127(19) 0.28(3) 0.42(4) 0.11(3) -0.09(2) -0.17(2) C49 0.063(11) 0.105(13) 0.150(16) 0.033(13) 0.017(10) 0.007(10) C50 0.080(12) 0.119(14) 0.137(15) 0.053(12) 0.026(11) 0.002(11) C51 0.177(17) 0.117(13) 0.078(11) -0.031(9) 0.059(11) -0.020(11) C52 0.58(5) 0.139(17) 0.053(11) -0.049(12) 0.068(19) 0.12(2) C53 0.16(2) 0.39(4) 0.17(2) 0.14(2) -0.058(17) -0.16(3) C54 0.045(11) 0.156(16) 0.46(4) 0.18(2) 0.021(16) -0.023(10) O1A 0.030(5) 0.095(6) 0.049(5) -0.012(4) -0.001(4) 0.015(4) O2A 0.058(6) 0.070(6) 0.041(5) -0.015(4) -0.003(4) 0.006(4) O3A 0.029(4) 0.071(5) 0.055(5) -0.015(4) 0.019(4) 0.009(4) O4A 0.043(5) 0.085(6) 0.034(4) -0.028(4) 0.009(4) -0.004(4) O5A 0.019(4) 0.079(5) 0.034(4) -0.007(4) 0.004(3) -0.003(4) O6A 0.047(5) 0.064(5) 0.037(4) 0.003(4) 0.003(4) 0.006(4) O7A 0.034(4) 0.055(5) 0.031(4) -0.008(4) 0.006(3) -0.008(4) O8A 0.035(4) 0.059(5) 0.031(4) -0.011(4) 0.018(3) -0.011(3) N1A 0.141(13) 0.053(8) 0.173(14) -0.058(8) 0.116(11) -0.019(8) N2A 0.139(13) 0.092(10) 0.093(9) -0.039(8) 0.049(9) 0.016(9) N3A 0.048(6) 0.047(6) 0.045(6) 0.007(5) 0.000(5) 0.009(5) N4A 0.035(6) 0.063(7) 0.045(6) -0.006(5) 0.005(4) 0.013(5) C1A 0.030(7) 0.057(8) 0.074(8) -0.014(7) 0.025(6) -0.001(6) C2A 0.018(6) 0.049(7) 0.068(8) -0.006(6) 0.013(6) -0.011(6) C3A 0.027(7) 0.058(9) 0.115(11) -0.053(8) 0.034(7) -0.028(6) C4A 0.055(10) 0.087(12) 0.071(11) -0.033(9) -0.032(9) 0.031(9) C5A 0.065(11) 0.092(11) 0.078(10) -0.012(8) 0.022(9) -0.010(9) C6A 0.033(7) 0.050(8) 0.062(8) -0.029(7) -0.003(6) 0.004(6) C7A 0.039(8) 0.055(8) 0.043(7) -0.017(6) 0.004(6) 0.003(6) C8A 0.050(8) 0.076(8) 0.037(7) 0.018(6) 0.007(6) 0.009(7) C9A 0.042(8) 0.064(8) 0.022(6) 0.006(6) 0.008(5) 0.015(6) C10A 0.045(7) 0.071(8) 0.020(6) -0.003(6) 0.000(5) -0.002(7) C11A 0.049(8) 0.041(7) 0.039(7) 0.003(6) 0.012(6) 0.016(6) C12A 0.025(6) 0.063(8) 0.035(6) 0.007(6) 0.009(5) 0.014(6) C13A 0.026(6) 0.065(8) 0.027(6) -0.003(6) 0.011(5) -0.003(6) C14A 0.038(7) 0.072(9) 0.024(6) 0.006(6) 0.010(5) 0.001(7) C15A 0.026(6) 0.059(7) 0.040(6) 0.000(6) 0.008(5) 0.004(5) C16A 0.031(7) 0.062(8) 0.028(6) 0.013(6) 0.008(5) -0.003(6) C17A 0.012(6) 0.080(9) 0.044(7) -0.015(7) 0.006(5) 0.001(6) C18A 0.032(7) 0.063(8) 0.036(7) 0.002(6) 0.003(5) 0.013(6) C19A 0.030(7) 0.049(7) 0.034(6) 0.005(5) -0.006(5) 0.000(5) C20A 0.014(6) 0.050(7) 0.027(6) -0.002(5) 0.002(4) 0.007(5) C21A 0.024(6) 0.034(7) 0.046(7) -0.002(6) 0.009(5) 0.017(5) C22A 0.035(7) 0.056(7) 0.033(6) -0.004(5) 0.010(5) 0.001(5) C23A 0.017(6) 0.054(7) 0.037(6) -0.002(6) 0.006(5) -0.004(5) C24A 0.031(7) 0.041(7) 0.063(8) -0.003(6) 0.010(6) -0.001(5) C25A 0.029(7) 0.049(7) 0.042(7) 0.001(6) 0.021(5) -0.005(6) C26A 0.028(7) 0.056(7) 0.048(7) -0.018(6) 0.007(5) -0.016(6) C27A 0.037(7) 0.043(7) 0.044(7) -0.003(6) 0.022(6) -0.014(6) C28A 0.038(7) 0.044(7) 0.037(7) -0.008(6) 0.009(6) -0.008(6) C29A 0.057(9) 0.053(8) 0.036(7) 0.005(6) 0.023(6) 0.022(7) C30A 0.023(6) 0.064(8) 0.024(6) 0.000(6) 0.007(5) -0.021(6) C31A 0.084(8) 0.108(9) 0.113(9) -0.014(7) -0.023(7) 0.056(7) C32A 0.31(4) 0.126(17) 0.19(2) 0.020(16) 0.09(2) -0.08(2) C33A 0.056(13) 0.30(3) 0.23(3) 0.01(2) -0.065(15) 0.053(16) C34A 0.053(10) 0.124(14) 0.085(11) -0.004(10) -0.008(9) 0.004(9) C35A 0.069(11) 0.143(14) 0.101(12) -0.040(10) 0.053(10) -0.020(10) C36A 0.066(11) 0.138(15) 0.179(17) -0.108(13) 0.081(11) -0.062(10) C37A 0.023(7) 0.092(10) 0.035(7) 0.007(7) -0.001(5) 0.009(7) C38A 0.050(9) 0.063(9) 0.099(11) 0.001(8) -0.001(7) 0.023(7) C39A 0.055(10) 0.080(10) 0.119(12) 0.006(9) 0.001(9) 0.021(8) C40A 0.067(10) 0.101(12) 0.055(9) -0.012(9) 0.023(7) 0.020(9) C41A 0.055(9) 0.113(12) 0.052(8) 0.024(8) 0.007(7) 0.013(9) C42A 0.060(9) 0.088(10) 0.049(8) 0.012(7) 0.016(7) 0.030(8) C43A 0.016(7) 0.101(11) 0.098(11) 0.020(9) -0.008(7) -0.010(7) C44A 0.029(7) 0.078(10) 0.131(13) 0.045(10) 0.018(7) 0.001(7) C45A 0.085(10) 0.082(10) 0.052(8) -0.026(7) 0.019(7) -0.007(7) C46A 0.079(10) 0.061(9) 0.054(8) -0.022(8) -0.013(7) 0.014(7) C47A 0.090(12) 0.142(14) 0.080(10) 0.024(10) 0.023(9) 0.019(10) C48A 0.054(10) 0.124(13) 0.26(2) 0.019(13) -0.064(12) -0.024(10) C49A 0.038(7) 0.113(11) 0.041(7) -0.006(7) 0.003(6) 0.033(7) C50A 0.057(9) 0.100(10) 0.062(9) 0.009(8) 0.035(7) -0.001(7) C51A 0.057(9) 0.110(11) 0.072(9) -0.038(8) 0.000(7) -0.001(8) C52A 0.062(8) 0.065(8) 0.046(7) -0.002(7) 0.023(6) -0.004(6) C53A 0.060(9) 0.096(10) 0.030(7) -0.009(7) 0.013(6) -0.021(8) C54A 0.107(12) 0.099(11) 0.044(8) -0.016(8) 0.029(7) -0.038(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 O1 C29 1.302(11) . ? O2 C29 1.283(10) . ? O3 C30 1.299(12) . ? O4 C30 1.265(12) . ? O5 C7 1.374(11) . ? O5 C43 1.485(16) . ? O6 C14 1.382(11) . ? O6 C46 1.441(13) . ? O7 C21 1.338(11) . ? O7 C49 1.493(17) . ? O8 C28 1.382(11) . ? O8 C52 1.69(3) . ? N1 N2 1.211(11) . ? N1 C4 1.490(14) . ? N2 C31 1.429(14) . ? N3 N4 1.192(12) . ? N3 C18 1.414(13) . ? N4 C37 1.451(14) . ? C1 C27 1.497(14) . ? C1 C2 1.516(14) . ? C2 C7 1.393(13) . ? C2 C3 1.397(13) . ? C3 C4 1.393(13) . ? C4 C5 1.431(14) . ? C5 C6 1.376(13) . ? C6 C7 1.390(13) . ? C6 C8 1.506(13) . ? C8 C9 1.501(13) . ? C9 C10 1.366(12) . ? C9 C14 1.417(13) . ? C10 C11 1.357(12) . ? C11 C12 1.394(12) . ? C11 C29 1.446(13) . ? C12 C13 1.378(12) . ? C13 C14 1.397(13) . ? C13 C15 1.536(13) . ? C15 C16 1.496(13) . ? C16 C17 1.389(13) . ? C16 C21 1.410(13) . ? C17 C18 1.377(14) . ? C18 C19 1.381(14) . ? C19 C20 1.399(14) . ? C20 C21 1.418(13) . ? C20 C22 1.553(13) . ? C22 C23 1.495(13) . ? C23 C28 1.378(13) . ? C23 C24 1.399(13) . ? C24 C25 1.410(13) . ? C25 C26 1.375(13) . ? C25 C30 1.474(14) . ? C26 C27 1.388(13) . ? C27 C28 1.425(13) . ? C31 C36 1.372(16) . ? C31 C32 1.394(16) . ? C32 C33 1.407(16) . ? C33 C34 1.389(17) . ? C34 C35 1.397(18) . ? C35 C36 1.357(17) . ? C37 C42 1.390(15) . ? C37 C38 1.399(16) . ? C38 C39 1.380(16) . ? C39 C40 1.415(17) . ? C40 C41 1.380(17) . ? C41 C42 1.372(16) . ? C43 C44 1.45(2) . ? C44 C45 1.25(5) . ? C46 C47 1.538(19) . ? C47 C48 1.56(2) . ? C49 C50 1.327(17) . ? C50 C51 1.67(2) . ? C52 C53 1.73(2) . ? C53 C54 1.36(2) . ? O1A C29A 1.263(12) . ? O2A C29A 1.263(11) . ? O3A C30A 1.287(11) . ? O4A C30A 1.266(10) . ? O5A C7A 1.388(11) . ? O5A C43A 1.475(13) . ? O6A C14A 1.381(11) . ? O6A C46A 1.429(13) . ? O7A C21A 1.363(10) . ? O7A C49A 1.445(12) . ? O8A C28A 1.379(10) . ? O8A C52A 1.456(11) . ? N1A N2A 1.220(8) . ? N1A C4A 1.644(16) . ? N2A C31A 1.691(14) . ? N3A N4A 1.216(9) . ? N3A C18A 1.450(12) . ? N4A C37A 1.460(13) . ? C1A C2A 1.500(14) . ? C1A C27A 1.527(13) . ? C2A C7A 1.364(13) . ? C2A C3A 1.421(14) . ? C3A C4A 1.407(17) . ? C4A C5A 1.248(16) . ? C5A C6A 1.396(15) . ? C6A C7A 1.410(13) . ? C6A C8A 1.526(14) . ? C8A C9A 1.529(13) . ? C9A C10A 1.391(13) . ? C9A C14A 1.400(13) . ? C10A C11A 1.369(13) . ? C11A C12A 1.413(13) . ? C11A C29A 1.462(14) . ? C12A C13A 1.362(12) . ? C13A C14A 1.385(13) . ? C13A C15A 1.516(12) . ? C15A C16A 1.484(12) . ? C16A C17A 1.380(13) . ? C16A C21A 1.405(12) . ? C17A C18A 1.352(13) . ? C18A C19A 1.389(13) . ? C19A C20A 1.383(12) . ? C20A C21A 1.361(12) . ? C20A C22A 1.540(12) . ? C22A C23A 1.519(12) . ? C23A C28A 1.366(12) . ? C23A C24A 1.370(12) . ? C24A C25A 1.406(13) . ? C25A C26A 1.413(12) . ? C25A C30A 1.464(13) . ? C26A C27A 1.408(12) . ? C27A C28A 1.402(13) . ? C31A C32A 1.367(9) . ? C31A C36A 1.399(9) . ? C32A C33A 1.28(2) . ? C33A C34A 1.40(2) . ? C34A C35A 1.348(17) . ? C35A C36A 1.526(15) . ? C37A C38A 1.340(14) . ? C37A C42A 1.382(14) . ? C38A C39A 1.394(16) . ? C39A C40A 1.382(16) . ? C40A C41A 1.343(16) . ? C41A C42A 1.397(15) . ? C43A C44A 1.407(15) . ? C44A C45A 1.604(16) . ? C46A C47A 1.460(16) . ? C47A C48A 1.612(18) . ? C49A C50A 1.501(14) . ? C50A C51A 1.582(15) . ? C52A C53A 1.474(14) . ? C53A C54A 1.444(15) . ? 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 C7 O5 C43 114.4(9) . . ? C14 O6 C46 113.0(8) . . ? C21 O7 C49 115.3(9) . . ? C28 O8 C52 107.2(8) . . ? N2 N1 C4 105.9(11) . . ? N1 N2 C31 109.2(11) . . ? N4 N3 C18 111.6(10) . . ? N3 N4 C37 116.6(12) . . ? C27 C1 C2 111.6(9) . . ? C7 C2 C3 118.3(11) . . ? C7 C2 C1 120.5(10) . . ? C3 C2 C1 121.0(10) . . ? C4 C3 C2 121.8(10) . . ? C3 C4 C5 117.3(11) . . ? C3 C4 N1 125.7(11) . . ? C5 C4 N1 117.0(11) . . ? C6 C5 C4 121.4(10) . . ? C5 C6 C7 118.9(10) . . ? C5 C6 C8 121.8(10) . . ? C7 C6 C8 118.7(9) . . ? O5 C7 C6 120.7(10) . . ? O5 C7 C2 117.7(10) . . ? C6 C7 C2 121.6(10) . . ? C9 C8 C6 109.4(9) . . ? C10 C9 C14 115.6(10) . . ? C10 C9 C8 121.3(10) . . ? C14 C9 C8 123.0(10) . . ? C11 C10 C9 124.4(10) . . ? C10 C11 C12 118.9(9) . . ? C10 C11 C29 121.8(10) . . ? C12 C11 C29 119.3(9) . . ? C13 C12 C11 120.4(9) . . ? C12 C13 C14 118.6(10) . . ? C12 C13 C15 121.6(10) . . ? C14 C13 C15 119.8(10) . . ? O6 C14 C13 120.7(10) . . ? O6 C14 C9 117.4(10) . . ? C13 C14 C9 121.7(10) . . ? C16 C15 C13 112.9(9) . . ? C17 C16 C21 119.8(10) . . ? C17 C16 C15 123.4(11) . . ? C21 C16 C15 116.6(10) . . ? C18 C17 C16 122.6(11) . . ? C19 C18 C17 117.7(11) . . ? C19 C18 N3 116.3(12) . . ? C17 C18 N3 126.1(11) . . ? C18 C19 C20 122.3(11) . . ? C19 C20 C21 119.2(11) . . ? C19 C20 C22 121.8(11) . . ? C21 C20 C22 117.9(10) . . ? O7 C21 C20 124.2(10) . . ? O7 C21 C16 117.5(10) . . ? C20 C21 C16 118.0(11) . . ? C23 C22 C20 109.5(8) . . ? C28 C23 C24 118.6(10) . . ? C28 C23 C22 122.8(10) . . ? C24 C23 C22 118.4(10) . . ? C23 C24 C25 119.2(10) . . ? C26 C25 C24 120.9(10) . . ? C26 C25 C30 121.2(11) . . ? C24 C25 C30 117.8(10) . . ? C25 C26 C27 121.1(10) . . ? C26 C27 C28 117.0(10) . . ? C26 C27 C1 120.2(10) . . ? C28 C27 C1 122.7(10) . . ? C23 C28 O8 120.2(10) . . ? C23 C28 C27 122.5(10) . . ? O8 C28 C27 117.0(10) . . ? O2 C29 O1 119.2(10) . . ? O2 C29 C11 117.9(10) . . ? O1 C29 C11 122.8(9) . . ? O4 C30 O3 122.7(11) . . ? O4 C30 C25 119.0(11) . . ? O3 C30 C25 118.0(11) . . ? C36 C31 C32 119.4(12) . . ? C36 C31 N2 125.0(13) . . ? C32 C31 N2 115.6(12) . . ? C31 C32 C33 119.2(13) . . ? C34 C33 C32 120.1(13) . . ? C33 C34 C35 119.1(13) . . ? C36 C35 C34 120.1(13) . . ? C35 C36 C31 122.0(13) . . ? C42 C37 C38 117.2(12) . . ? C42 C37 N4 121.0(13) . . ? C38 C37 N4 121.7(13) . . ? C39 C38 C37 122.9(14) . . ? C38 C39 C40 117.1(14) . . ? C41 C40 C39 121.2(14) . . ? C42 C41 C40 119.3(14) . . ? C41 C42 C37 122.1(14) . . ? C44 C43 O5 112.9(15) . . ? C45 C44 C43 123(2) . . ? O6 C46 C47 108.5(12) . . ? C46 C47 C48 121.9(19) . . ? C50 C49 O7 110.2(15) . . ? C49 C50 C51 107.6(14) . . ? C53 C52 O8 83.2(11) . . ? C52 C53 C54 98.3(19) . . ? C7A O5A C43A 115.7(7) . . ? C14A O6A C46A 111.6(8) . . ? C21A O7A C49A 116.0(7) . . ? C28A O8A C52A 112.8(7) . . ? N2A N1A C4A 101.7(11) . . ? N1A N2A C31A 104.4(10) . . ? N4A N3A C18A 112.3(9) . . ? N3A N4A C37A 114.3(9) . . ? C2A C1A C27A 113.3(9) . . ? C7A C2A C3A 116.3(11) . . ? C7A C2A C1A 119.7(10) . . ? C3A C2A C1A 123.5(10) . . ? C4A C3A C2A 115.2(10) . . ? C5A C4A C3A 129.3(12) . . ? C5A C4A N1A 107.7(14) . . ? C3A C4A N1A 122.9(11) . . ? C4A C5A C6A 117.2(14) . . ? C5A C6A C7A 117.8(11) . . ? C5A C6A C8A 121.0(11) . . ? C7A C6A C8A 121.0(10) . . ? C2A C7A O5A 122.3(10) . . ? C2A C7A C6A 123.6(11) . . ? O5A C7A C6A 113.7(10) . . ? C6A C8A C9A 107.7(9) . . ? C10A C9A C14A 118.2(10) . . ? C10A C9A C8A 121.9(10) . . ? C14A C9A C8A 119.8(10) . . ? C11A C10A C9A 121.5(10) . . ? C10A C11A C12A 117.5(10) . . ? C10A C11A C29A 119.7(11) . . ? C12A C11A C29A 122.7(10) . . ? C13A C12A C11A 123.4(9) . . ? C12A C13A C14A 116.8(10) . . ? C12A C13A C15A 117.9(10) . . ? C14A C13A C15A 125.0(10) . . ? O6A C14A C13A 117.5(10) . . ? O6A C14A C9A 120.1(10) . . ? C13A C14A C9A 122.3(11) . . ? C16A C15A C13A 112.5(8) . . ? C17A C16A C21A 115.7(10) . . ? C17A C16A C15A 124.3(9) . . ? C21A C16A C15A 119.2(9) . . ? C18A C17A C16A 123.4(10) . . ? C17A C18A C19A 119.5(10) . . ? C17A C18A N3A 115.3(10) . . ? C19A C18A N3A 125.1(10) . . ? C20A C19A C18A 118.8(9) . . ? C21A C20A C19A 120.2(9) . . ? C21A C20A C22A 120.9(8) . . ? C19A C20A C22A 118.7(9) . . ? C20A C21A O7A 118.4(9) . . ? C20A C21A C16A 121.7(9) . . ? O7A C21A C16A 119.6(9) . . ? C23A C22A C20A 110.0(7) . . ? C28A C23A C24A 119.9(9) . . ? C28A C23A C22A 121.8(9) . . ? C24A C23A C22A 118.3(9) . . ? C23A C24A C25A 120.9(9) . . ? C24A C25A C26A 118.7(9) . . ? C24A C25A C30A 121.3(10) . . ? C26A C25A C30A 119.9(10) . . ? C27A C26A C25A 120.0(9) . . ? C28A C27A C26A 118.0(9) . . ? C28A C27A C1A 123.7(9) . . ? C26A C27A C1A 118.2(9) . . ? C23A C28A O8A 120.1(9) . . ? C23A C28A C27A 122.0(9) . . ? O8A C28A C27A 117.8(9) . . ? O2A C29A O1A 121.5(11) . . ? O2A C29A C11A 116.1(11) . . ? O1A C29A C11A 122.3(10) . . ? O4A C30A O3A 121.7(9) . . ? O4A C30A C25A 120.2(10) . . ? O3A C30A C25A 118.0(9) . . ? C32A C31A C36A 123.6(10) . . ? C32A C31A N2A 116.7(16) . . ? C36A C31A N2A 119.0(12) . . ? C33A C32A C31A 127.7(18) . . ? C32A C33A C34A 110.8(16) . . ? C35A C34A C33A 129.5(13) . . ? C34A C35A C36A 116.4(10) . . ? C31A C36A C35A 111.1(8) . . ? C38A C37A C42A 120.3(12) . . ? C38A C37A N4A 118.6(11) . . ? C42A C37A N4A 121.1(12) . . ? C37A C38A C39A 122.4(13) . . ? C40A C39A C38A 116.6(13) . . ? C41A C40A C39A 122.0(12) . . ? C40A C41A C42A 120.5(12) . . ? C37A C42A C41A 118.2(12) . . ? C44A C43A O5A 113.2(11) . . ? C43A C44A C45A 108.5(11) . . ? O6A C46A C47A 108.4(10) . . ? C46A C47A C48A 111.3(12) . . ? O7A C49A C50A 111.9(10) . . ? C49A C50A C51A 109.1(10) . . ? O8A C52A C53A 108.1(8) . . ? C54A C53A C52A 118.7(10) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 26.42 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.635 _refine_diff_density_min -0.424 _refine_diff_density_rms 0.086