Electronic Supplementary Material for CrystEngComm This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _publ_section_title ;Cholic acid as host for long linear molecules: a series of co-crystals with n-alkylammonia ; _publ_section_abstract ;The novel asymmetrical catanionic surfactants, decylammonium, dodecylammonium, tetradecylammonium, and hexadecylammonium cholates were synthesized and their crystal structure was determined. These structures represent first examples of cholic acid (CA) cocrystals with molecules of comparable or larger size. The CA to guest ratio in crystals was found to be 1:1 in three cases and 2:1 in one case. In 1:1 complexes the CA molecules are assembled in bilayers and n-alkylammonia guests are included in the hydrophobic zone between those layers in a kind of sandwich-type structure. In the 2:1 complex the CA molecules include guest molecules in a different way: instead of being parallel, bilayers cross and form one-dimensional hydrophobic channels into which guest molecules are included. In the case of 1:1 cocrystals the bilayers of CA are separated much more than in previously reported structures in order to accomodate large n-alkylammonia molecules. Nevertheless the characteristic dimension in the plane of bilayers, corresponding to the crystallographic b axis, remains remarkably constant (approximately 7.9 \%A) in all four structures. ; _publ_contact_author_name 'Zoran Stefanic' _publ_contact_author_address ; Rudjer Bo\2sigma(I) _diffrn_reflns_reduction_process ; ; #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'CAD4 Express (Enraf Nonius, 1994)' _computing_cell_refinement 'CAD4 Express (Enraf Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'PLATON (Spek, 2003)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0764P)^2^+0.5450P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary ' ?' _atom_sites_solution_secondary ' ?' _atom_sites_solution_hydrogens ' ?' _refine_ls_hydrogen_treatment ' ?' _refine_ls_extinction_method none _refine_ls_number_reflns 3831 _refine_ls_number_parameters 398 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0628 _refine_ls_R_factor_gt 0.0488 _refine_ls_wR_factor_ref 0.1517 _refine_ls_wR_factor_gt 0.1402 _refine_ls_goodness_of_fit_ref 1.089 _refine_ls_restrained_S_all 1.088 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H.D. (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.2(3) _refine_diff_density_max 0.252 _refine_diff_density_min -0.215 _refine_diff_density_rms 0.041 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags O1 O 0.6881(3) 0.2027(4) 0.5834(2) 0.0796(13) Uani 1 . . O2 O 0.68627(17) -0.2369(3) 0.34638(17) 0.0479(8) Uani 1 . . O3 O 0.61410(16) 0.2232(3) 0.18656(16) 0.0480(7) Uani 1 . . O4 O 0.53299(18) 0.0269(5) -0.38493(16) 0.0621(9) Uani 1 . . O5 O 0.42427(16) -0.0125(4) -0.29776(17) 0.0521(8) Uani 1 . . C1 C 0.8691(2) 0.2722(5) 0.4354(2) 0.0458(10) Uani 1 . . C2 C 0.7822(3) 0.3045(5) 0.4782(2) 0.0478(10) Uani 1 . . C3 C 0.7705(3) 0.1680(5) 0.5462(2) 0.0520(11) Uani 1 . . C4 C 0.7703(3) -0.0060(5) 0.5042(2) 0.0475(10) Uani 1 . . C5 C 0.8540(2) -0.0399(4) 0.4550(2) 0.0456(10) Uani 1 . . C6 C 0.8491(3) -0.2152(5) 0.4092(2) 0.0467(10) Uani 1 . . C7 C 0.7782(2) -0.2305(4) 0.3226(2) 0.0416(9) Uani 1 . . C8 C 0.7868(2) -0.0836(4) 0.2565(2) 0.0369(9) Uani 1 . . C9 C 0.7868(2) 0.0883(4) 0.3058(2) 0.0349(8) Uani 1 . . C10 C 0.8687(2) 0.1011(5) 0.3863(2) 0.0413(9) Uani 1 . . C11 C 0.7807(2) 0.2405(4) 0.2418(2) 0.0412(10) Uani 1 . . C12 C 0.7046(2) 0.2245(4) 0.1593(2) 0.0403(9) Uani 1 . . C13 C 0.7170(2) 0.0612(4) 0.10784(19) 0.0355(8) Uani 1 . . C14 C 0.7119(2) -0.0875(4) 0.1735(2) 0.0362(9) Uani 1 . . C15 C 0.7051(3) -0.2440(4) 0.1130(2) 0.0451(10) Uani 1 . . C16 C 0.6517(3) -0.1823(4) 0.0211(2) 0.0459(10) Uani 1 . . C17 C 0.6381(2) 0.0114(4) 0.0290(2) 0.0388(9) Uani 1 . . C18 C 0.8112(2) 0.0662(5) 0.0716(2) 0.0481(10) Uani 1 . . C19 C 0.9643(2) 0.0833(6) 0.3550(3) 0.0573(11) Uani 1 . . C20 C 0.6348(2) 0.1050(5) -0.0617(2) 0.0434(10) Uani 1 . . C21 C 0.6188(3) 0.2958(5) -0.0529(3) 0.0632(14) Uani 1 . . C22 C 0.5604(2) 0.0316(5) -0.1359(2) 0.0468(10) Uani 1 . . C23 C 0.5744(3) 0.0892(6) -0.2300(2) 0.0566(13) Uani 1 . . C24 C 0.5048(2) 0.0280(4) -0.3095(2) 0.0442(10) Uani 1 . . N1 N 0.4269(2) -0.0084(5) 0.44974(19) 0.0503(10) Uani 1 . . C25 C -0.0584(7) 0.0372(14) -0.2565(4) 0.154(4) Uani 1 . . C26 C -0.0426(6) -0.0305(13) -0.1637(5) 0.138(3) Uani 1 . . C27 C 0.0360(4) 0.0397(10) -0.1074(3) 0.092(2) Uani 1 . . C28 C 0.0524(3) -0.0157(9) -0.0076(3) 0.0812(19) Uani 1 . . C29 C 0.1336(3) 0.0639(8) 0.0461(3) 0.0738(16) Uani 1 . . C30 C 0.1542(3) 0.0151(8) 0.1462(3) 0.0761(18) Uani 1 . . C31 C 0.2326(3) 0.1141(7) 0.1948(3) 0.0705(16) Uani 1 . . C32 C 0.2611(3) 0.0713(7) 0.2954(3) 0.0698(16) Uani 1 . . C33 C 0.3371(3) 0.1853(6) 0.3376(3) 0.0632(14) Uani 1 . . C34 C 0.3733(3) 0.1511(6) 0.4362(3) 0.0583(12) Uani 1 . . O1W O 0.5444(2) 0.9983(5) 0.3189(2) 0.0773(11) Uani 1 . . H1A H 0.92302 0.27671 0.48236 0.055 Uiso 1 . . H1B H 0.87552 0.36171 0.39245 0.055 Uiso 1 . . H1O H 0.645(5) 0.134(10) 0.591(5) 0.12(3) Uiso 1 . . H2A H 0.78712 0.41353 0.50808 0.0573 Uiso 1 . . H2B H 0.72813 0.30667 0.43138 0.0573 Uiso 1 . . H2O H 0.655(3) -0.322(8) 0.326(3) 0.076(15) Uiso 1 . . H3 H 0.82337 0.17454 0.59523 0.0621 Uiso 1 . . H3O H 0.60663 0.31024 0.21429 0.072 Uiso 1 . . H4A H 0.71354 -0.01954 0.46142 0.0571 Uiso 1 . . H4B H 0.76972 -0.08983 0.55144 0.0571 Uiso 1 . . H5 H 0.90941 -0.04019 0.50133 0.0547 Uiso 1 . . H6A H 0.91025 -0.24271 0.39477 0.056 Uiso 1 . . H6B H 0.83396 -0.29841 0.4524 0.056 Uiso 1 . . H7 H 0.78991 -0.33652 0.29231 0.0499 Uiso 1 . . H8 H 0.84709 -0.09501 0.23523 0.0443 Uiso 1 . . H9 H 0.72957 0.09038 0.33323 0.0418 Uiso 1 . . H11A H 0.84035 0.25488 0.22095 0.0494 Uiso 1 . . H11B H 0.76901 0.34104 0.27545 0.0494 Uiso 1 . . H12 H 0.70894 0.32075 0.11883 0.0483 Uiso 1 . . H14 H 0.65201 -0.07759 0.19586 0.0434 Uiso 1 . . H15A H 0.67122 -0.33362 0.13805 0.0541 Uiso 1 . . H15B H 0.76653 -0.28509 0.10596 0.0541 Uiso 1 . . H16A H 0.59183 -0.23834 0.00818 0.0551 Uiso 1 . . H16B H 0.68709 -0.20725 -0.02751 0.0551 Uiso 1 . . H17 H 0.57829 0.02991 0.05041 0.0465 Uiso 1 . . H18A H 0.81915 -0.03637 0.03927 0.0721 Uiso 1 . . H18B H 0.86091 0.07721 0.12141 0.0721 Uiso 1 . . H18C H 0.81211 0.16071 0.03145 0.0721 Uiso 1 . . H19A H 0.96697 -0.02194 0.32351 0.0858 Uiso 1 . . H19B H 1.01223 0.08576 0.40672 0.0858 Uiso 1 . . H19C H 0.97335 0.17484 0.31504 0.0858 Uiso 1 . . H20 H 0.69548 0.08989 -0.08187 0.0521 Uiso 1 . . H21A H 0.66517 0.34159 -0.00674 0.095 Uiso 1 . . H21B H 0.55806 0.315 -0.03682 0.095 Uiso 1 . . H21C H 0.62305 0.35004 -0.10968 0.095 Uiso 1 . . H22A H 0.56281 -0.0907 -0.13319 0.0562 Uiso 1 . . H22B H 0.49918 0.06666 -0.12453 0.0562 Uiso 1 . . H23A H 0.57391 0.21161 -0.23069 0.0678 Uiso 1 . . H23B H 0.63593 0.05338 -0.23996 0.0678 Uiso 1 . . H1N H 0.472(2) -0.019(7) 0.405(2) 0.072(13) Uiso 1 . . H2N H 0.464(2) -0.024(8) 0.5102(18) 0.083(15) Uiso 1 . . H3N H 0.381(3) -0.102(6) 0.438(4) 0.11(2) Uiso 1 . . H25A H -0.11113 -0.01805 -0.29061 0.2309 Uiso 1 . . H25B H -0.00422 0.01739 -0.28479 0.2309 Uiso 1 . . H25C H -0.07002 0.15631 -0.25453 0.2309 Uiso 1 . . H26A H -0.09772 -0.00969 -0.13575 0.1655 Uiso 1 . . H26B H -0.03443 -0.15178 -0.16664 0.1655 Uiso 1 . . H27A H 0.02979 0.16165 -0.10904 0.1105 Uiso 1 . . H27B H 0.09121 0.01167 -0.13368 0.1105 Uiso 1 . . H28A H -0.00253 0.01127 0.01948 0.0974 Uiso 1 . . H28B H 0.06044 -0.13726 -0.00495 0.0974 Uiso 1 . . H29A H 0.12514 0.18533 0.04235 0.0882 Uiso 1 . . H29B H 0.18793 0.03699 0.01813 0.0882 Uiso 1 . . H30A H 0.0991 0.03397 0.17438 0.0915 Uiso 1 . . H30B H 0.16929 -0.10418 0.15122 0.0915 Uiso 1 . . H31A H 0.21607 0.23272 0.18994 0.0849 Uiso 1 . . H31B H 0.28629 0.09801 0.16415 0.0849 Uiso 1 . . H32A H 0.20757 0.08307 0.32678 0.0837 Uiso 1 . . H32B H 0.282 -0.04496 0.30128 0.0837 Uiso 1 . . H33A H 0.31462 0.30066 0.33209 0.0759 Uiso 1 . . H33B H 0.3887 0.17641 0.30347 0.0759 Uiso 1 . . H34A H 0.41277 0.24408 0.4604 0.0696 Uiso 1 . . H34B H 0.32109 0.14555 0.46977 0.0696 Uiso 1 . . H1W H 0.562(4) 1.045(10) 0.263(3) 0.14(2) Uiso 1 . . H2W H 0.596(3) 0.917(5) 0.322(3) 0.079(15) Uiso 1 . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.112(3) 0.0468(16) 0.094(2) -0.0117(17) 0.061(2) -0.0117(18) O2 0.0533(13) 0.0364(13) 0.0553(13) -0.0036(12) 0.0124(11) -0.0085(11) O3 0.0517(12) 0.0396(13) 0.0527(12) -0.0108(11) 0.0078(10) 0.0097(10) O4 0.0600(14) 0.087(2) 0.0386(12) 0.0014(14) 0.0051(10) -0.0053(15) O5 0.0467(12) 0.0525(15) 0.0548(13) 0.0185(12) 0.0002(10) -0.0017(12) C1 0.0521(18) 0.0415(19) 0.0418(16) -0.0042(15) 0.0002(14) -0.0150(15) C2 0.066(2) 0.0350(18) 0.0423(16) -0.0069(14) 0.0078(15) -0.0069(16) C3 0.073(2) 0.045(2) 0.0380(16) -0.0057(15) 0.0088(15) -0.0065(18) C4 0.068(2) 0.0355(17) 0.0391(15) 0.0027(15) 0.0085(14) -0.0064(16) C5 0.0511(17) 0.0379(19) 0.0440(16) 0.0009(14) -0.0049(14) -0.0016(15) C6 0.0537(19) 0.0353(17) 0.0489(18) 0.0032(15) 0.0005(14) 0.0080(15) C7 0.0477(17) 0.0314(16) 0.0458(16) -0.0028(14) 0.0076(13) 0.0033(14) C8 0.0403(15) 0.0306(15) 0.0399(15) -0.0038(13) 0.0063(12) 0.0020(12) C9 0.0386(14) 0.0293(15) 0.0364(14) -0.0044(12) 0.0046(11) -0.0047(12) C10 0.0420(15) 0.0388(18) 0.0411(15) -0.0034(14) 0.0002(12) -0.0068(14) C11 0.0520(18) 0.0307(17) 0.0407(16) -0.0018(13) 0.0063(13) -0.0075(14) C12 0.0496(17) 0.0315(16) 0.0396(15) -0.0015(13) 0.0063(13) 0.0006(14) C13 0.0383(14) 0.0340(16) 0.0345(14) -0.0031(13) 0.0068(11) 0.0003(12) C14 0.0403(15) 0.0306(15) 0.0383(15) -0.0068(13) 0.0083(12) 0.0002(13) C15 0.0545(19) 0.0333(17) 0.0472(18) -0.0096(15) 0.0068(14) -0.0001(15) C16 0.0532(18) 0.0385(19) 0.0458(17) -0.0114(15) 0.0066(14) 0.0003(15) C17 0.0407(14) 0.0399(17) 0.0365(14) -0.0062(14) 0.0079(11) -0.0013(14) C18 0.0445(16) 0.055(2) 0.0462(16) -0.0036(16) 0.0115(13) -0.0046(16) C19 0.0425(17) 0.060(2) 0.068(2) -0.005(2) 0.0037(15) -0.0066(17) C20 0.0495(17) 0.0427(19) 0.0375(15) -0.0026(14) 0.0048(12) -0.0033(15) C21 0.091(3) 0.044(2) 0.050(2) 0.0042(18) -0.0043(19) -0.004(2) C22 0.0513(17) 0.050(2) 0.0386(15) 0.0028(15) 0.0047(13) -0.0040(16) C23 0.059(2) 0.070(3) 0.0400(16) -0.0024(18) 0.0053(14) -0.013(2) C24 0.0503(17) 0.0386(18) 0.0413(16) 0.0089(14) -0.0005(13) 0.0008(14) N1 0.0543(16) 0.0569(19) 0.0390(14) 0.0042(15) 0.0045(12) 0.0051(16) C25 0.222(9) 0.141(8) 0.083(4) 0.012(5) -0.031(5) 0.018(7) C26 0.161(6) 0.124(7) 0.113(5) 0.010(5) -0.030(5) -0.017(6) C27 0.087(3) 0.103(5) 0.081(3) -0.009(3) -0.002(3) -0.007(3) C28 0.073(3) 0.090(4) 0.081(3) -0.004(3) 0.013(2) 0.007(3) C29 0.077(3) 0.076(3) 0.067(2) 0.009(2) 0.006(2) 0.005(3) C30 0.079(3) 0.081(4) 0.067(2) 0.012(3) 0.007(2) -0.003(3) C31 0.085(3) 0.068(3) 0.056(2) 0.010(2) 0.002(2) -0.001(2) C32 0.087(3) 0.064(3) 0.057(2) 0.011(2) 0.006(2) -0.002(2) C33 0.070(2) 0.062(3) 0.057(2) 0.009(2) 0.0079(18) 0.009(2) C34 0.067(2) 0.056(2) 0.052(2) 0.0017(18) 0.0089(17) 0.0071(19) O1W 0.0745(19) 0.069(2) 0.099(2) 0.017(2) 0.0472(17) 0.0179(18) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C3 1.420(6) . . yes O2 C7 1.433(4) . . yes O3 C12 1.433(4) . . yes O4 C24 1.254(4) . . yes O5 C24 1.250(4) . . yes O1 H1O 0.85(7) . . no O2 H2O 0.84(6) . . no O3 H3O 0.82 . . no O1W H2W 0.98(4) . . no O1W H1W 0.98(5) . . no N1 C34 1.482(6) . . yes N1 H3N 1.00(5) . . no N1 H2N 0.99(3) . . no N1 H1N 1.01(3) . . no C1 C10 1.540(5) . . no C1 C2 1.519(5) . . no C2 C3 1.510(5) . . no C3 C4 1.514(5) . . no C4 C5 1.535(5) . . no C5 C10 1.552(5) . . no C5 C6 1.545(5) . . no C6 C7 1.532(5) . . no C7 C8 1.543(4) . . no C8 C14 1.522(4) . . no C8 C9 1.548(4) . . no C9 C10 1.562(4) . . no C9 C11 1.532(4) . . no C10 C19 1.536(4) . . no C11 C12 1.532(4) . . no C12 C13 1.529(4) . . no C13 C14 1.541(4) . . no C13 C18 1.545(4) . . no C13 C17 1.565(4) . . no C14 C15 1.528(4) . . no C15 C16 1.550(5) . . no C16 C17 1.554(4) . . no C17 C20 1.538(4) . . no C20 C21 1.538(6) . . no C20 C22 1.541(4) . . no C22 C23 1.519(4) . . no C23 C24 1.519(5) . . no C1 H1B 0.97 . . no C1 H1A 0.97 . . no C2 H2A 0.97 . . no C2 H2B 0.97 . . no C3 H3 0.98 . . no C4 H4A 0.97 . . no C4 H4B 0.97 . . no C5 H5 0.98 . . no C6 H6A 0.97 . . no C6 H6B 0.97 . . no C7 H7 0.98 . . no C8 H8 0.98 . . no C9 H9 0.98 . . no C11 H11A 0.97 . . no C11 H11B 0.97 . . no C12 H12 0.98 . . no C14 H14 0.98 . . no C15 H15B 0.97 . . no C15 H15A 0.97 . . no C16 H16B 0.97 . . no C16 H16A 0.97 . . no C17 H17 0.98 . . no C18 H18C 0.96 . . no C18 H18B 0.96 . . no C18 H18A 0.96 . . no C19 H19C 0.96 . . no C19 H19A 0.96 . . no C19 H19B 0.96 . . no C20 H20 0.98 . . no C21 H21B 0.96 . . no C21 H21C 0.96 . . no C21 H21A 0.96 . . no C22 H22A 0.97 . . no C22 H22B 0.97 . . no C23 H23B 0.97 . . no C23 H23A 0.97 . . no C25 C26 1.471(10) . . no C26 C27 1.425(10) . . no C27 C28 1.537(7) . . no C28 C29 1.466(7) . . no C29 C30 1.529(6) . . no C30 C31 1.480(7) . . no C31 C32 1.534(6) . . no C32 C33 1.491(7) . . no C33 C34 1.511(6) . . no C25 H25B 0.96 . . no C25 H25C 0.96 . . no C25 H25A 0.96 . . no C26 H26A 0.97 . . no C26 H26B 0.97 . . no C27 H27A 0.97 . . no C27 H27B 0.97 . . no C28 H28A 0.97 . . no C28 H28B 0.97 . . no C29 H29B 0.97 . . no C29 H29A 0.97 . . no C30 H30A 0.97 . . no C30 H30B 0.97 . . no C31 H31A 0.97 . . no C31 H31B 0.97 . . no C32 H32B 0.97 . . no C32 H32A 0.97 . . no C33 H33A 0.97 . . no C33 H33B 0.97 . . no C34 H34B 0.97 . . no C34 H34A 0.97 . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 O1 H1O 128(5) . . . no C7 O2 H2O 114(3) . . . no C12 O3 H3O 109 . . . no H1W O1W H2W 90(5) . . . no H1N N1 H3N 108(4) . . . no H2N N1 H3N 109(5) . . . no C34 N1 H2N 116(3) . . . no C34 N1 H1N 111(3) . . . no H1N N1 H2N 106(2) . . . no C34 N1 H3N 107(3) . . . no C2 C1 C10 113.8(3) . . . no C1 C2 C3 110.3(3) . . . no O1 C3 C4 112.9(3) . . . yes C2 C3 C4 111.5(3) . . . no O1 C3 C2 108.1(3) . . . yes C3 C4 C5 113.9(3) . . . no C4 C5 C10 112.8(3) . . . no C6 C5 C10 110.9(3) . . . no C4 C5 C6 112.4(3) . . . no C5 C6 C7 115.2(3) . . . no O2 C7 C6 109.1(3) . . . yes C6 C7 C8 111.8(3) . . . no O2 C7 C8 110.7(2) . . . yes C9 C8 C14 110.7(2) . . . no C7 C8 C14 112.9(2) . . . no C7 C8 C9 110.7(2) . . . no C8 C9 C11 113.6(2) . . . no C10 C9 C11 113.2(3) . . . no C8 C9 C10 111.6(3) . . . no C1 C10 C9 111.8(3) . . . no C1 C10 C5 108.1(2) . . . no C9 C10 C19 112.3(3) . . . no C5 C10 C9 107.3(3) . . . no C5 C10 C19 110.8(3) . . . no C1 C10 C19 106.6(3) . . . no C9 C11 C12 113.8(3) . . . no C11 C12 C13 110.4(2) . . . no O3 C12 C11 110.8(2) . . . yes O3 C12 C13 108.6(2) . . . yes C17 C13 C18 109.3(2) . . . no C12 C13 C14 107.9(2) . . . no C12 C13 C18 109.3(3) . . . no C14 C13 C18 111.8(3) . . . no C14 C13 C17 100.7(2) . . . no C12 C13 C17 117.6(2) . . . no C8 C14 C13 113.9(2) . . . no C13 C14 C15 104.4(2) . . . no C8 C14 C15 118.2(3) . . . no C14 C15 C16 104.3(3) . . . no C15 C16 C17 107.3(2) . . . no C16 C17 C20 113.4(3) . . . no C13 C17 C20 117.6(3) . . . no C13 C17 C16 102.6(2) . . . no C17 C20 C21 112.6(3) . . . no C17 C20 C22 112.1(3) . . . no C21 C20 C22 109.5(3) . . . no C20 C22 C23 112.0(3) . . . no C22 C23 C24 117.5(3) . . . no O5 C24 C23 120.0(3) . . . yes O4 C24 O5 124.2(3) . . . yes O4 C24 C23 115.8(3) . . . yes H1A C1 H1B 108 . . . no C2 C1 H1B 109 . . . no C10 C1 H1A 109 . . . no C10 C1 H1B 109 . . . no C2 C1 H1A 109 . . . no C1 C2 H2B 110 . . . no C3 C2 H2A 110 . . . no H2A C2 H2B 108 . . . no C1 C2 H2A 110 . . . no C3 C2 H2B 110 . . . no O1 C3 H3 108 . . . no C4 C3 H3 108 . . . no C2 C3 H3 108 . . . no C3 C4 H4A 109 . . . no C5 C4 H4B 109 . . . no C5 C4 H4A 109 . . . no C3 C4 H4B 109 . . . no H4A C4 H4B 108 . . . no C4 C5 H5 107 . . . no C10 C5 H5 107 . . . no C6 C5 H5 107 . . . no C5 C6 H6B 108 . . . no C7 C6 H6A 109 . . . no H6A C6 H6B 108 . . . no C7 C6 H6B 108 . . . no C5 C6 H6A 108 . . . no C8 C7 H7 108 . . . no O2 C7 H7 108 . . . no C6 C7 H7 108 . . . no C14 C8 H8 107 . . . no C9 C8 H8 107 . . . no C7 C8 H8 107 . . . no C11 C9 H9 106 . . . no C10 C9 H9 106 . . . no C8 C9 H9 106 . . . no H11A C11 H11B 108 . . . no C9 C11 H11B 109 . . . no C9 C11 H11A 109 . . . no C12 C11 H11B 109 . . . no C12 C11 H11A 109 . . . no C11 C12 H12 109 . . . no O3 C12 H12 109 . . . no C13 C12 H12 109 . . . no C13 C14 H14 107 . . . no C15 C14 H14 106 . . . no C8 C14 H14 107 . . . no C16 C15 H15A 111 . . . no C14 C15 H15A 111 . . . no C16 C15 H15B 111 . . . no H15A C15 H15B 109 . . . no C14 C15 H15B 111 . . . no C15 C16 H16B 110 . . . no C15 C16 H16A 110 . . . no H16A C16 H16B 109 . . . no C17 C16 H16A 110 . . . no C17 C16 H16B 110 . . . no C20 C17 H17 108 . . . no C13 C17 H17 108 . . . no C16 C17 H17 108 . . . no C13 C18 H18B 110 . . . no H18A C18 H18C 109 . . . no C13 C18 H18C 110 . . . no C13 C18 H18A 109 . . . no H18B C18 H18C 109 . . . no H18A C18 H18B 109 . . . no C10 C19 H19C 109 . . . no C10 C19 H19B 109 . . . no H19A C19 H19B 109 . . . no C10 C19 H19A 109 . . . no H19B C19 H19C 110 . . . no H19A C19 H19C 109 . . . no C22 C20 H20 107 . . . no C21 C20 H20 107 . . . no C17 C20 H20 107 . . . no C20 C21 H21B 109 . . . no C20 C21 H21C 110 . . . no H21B C21 H21C 109 . . . no H21A C21 H21B 109 . . . no C20 C21 H21A 110 . . . no H21A C21 H21C 109 . . . no C23 C22 H22B 109 . . . no C20 C22 H22B 109 . . . no C23 C22 H22A 109 . . . no C20 C22 H22A 109 . . . no H22A C22 H22B 108 . . . no C22 C23 H23B 108 . . . no H23A C23 H23B 107 . . . no C22 C23 H23A 108 . . . no C24 C23 H23A 108 . . . no C24 C23 H23B 108 . . . no C25 C26 C27 114.3(8) . . . no C26 C27 C28 117.0(6) . . . no C27 C28 C29 113.7(5) . . . no C28 C29 C30 116.7(4) . . . no C29 C30 C31 111.6(4) . . . no C30 C31 C32 116.0(4) . . . no C31 C32 C33 110.7(4) . . . no C32 C33 C34 115.5(4) . . . no N1 C34 C33 112.6(4) . . . yes C26 C25 H25A 109 . . . no C26 C25 H25B 109 . . . no H25A C25 H25B 110 . . . no H25A C25 H25C 110 . . . no C26 C25 H25C 109 . . . no H25B C25 H25C 109 . . . no C25 C26 H26B 109 . . . no C27 C26 H26A 109 . . . no C27 C26 H26B 109 . . . no H26A C26 H26B 108 . . . no C25 C26 H26A 109 . . . no C26 C27 H27A 108 . . . no C26 C27 H27B 108 . . . no C28 C27 H27B 108 . . . no H27A C27 H27B 107 . . . no C28 C27 H27A 108 . . . no C27 C28 H28A 109 . . . no C29 C28 H28A 109 . . . no C29 C28 H28B 109 . . . no C27 C28 H28B 109 . . . no H28A C28 H28B 108 . . . no C28 C29 H29B 108 . . . no C30 C29 H29A 108 . . . no C30 C29 H29B 108 . . . no H29A C29 H29B 107 . . . no C28 C29 H29A 108 . . . no C29 C30 H30B 109 . . . no C31 C30 H30A 109 . . . no C29 C30 H30A 109 . . . no H30A C30 H30B 108 . . . no C31 C30 H30B 109 . . . no C30 C31 H31A 108 . . . no C30 C31 H31B 108 . . . no C32 C31 H31B 108 . . . no H31A C31 H31B 107 . . . no C32 C31 H31A 108 . . . no C31 C32 H32B 109 . . . no C33 C32 H32A 110 . . . no C33 C32 H32B 110 . . . no H32A C32 H32B 108 . . . no C31 C32 H32A 109 . . . no C32 C33 H33B 108 . . . no C34 C33 H33A 108 . . . no C32 C33 H33A 108 . . . no H33A C33 H33B 108 . . . no C34 C33 H33B 108 . . . no N1 C34 H34A 109 . . . no N1 C34 H34B 109 . . . no C33 C34 H34B 109 . . . no H34A C34 H34B 108 . . . no C33 C34 H34A 109 . . . no loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2 C1 C10 C19 -175.1(3) . . . . no C10 C1 C2 C3 58.9(4) . . . . no C2 C1 C10 C5 -56.0(3) . . . . no C2 C1 C10 C9 61.9(3) . . . . no C1 C2 C3 O1 -179.4(3) . . . . no C1 C2 C3 C4 -54.7(4) . . . . no C2 C3 C4 C5 52.2(4) . . . . no O1 C3 C4 C5 174.1(3) . . . . no C3 C4 C5 C10 -51.0(4) . . . . no C3 C4 C5 C6 -177.3(3) . . . . no C4 C5 C10 C9 -69.9(3) . . . . no C4 C5 C10 C1 50.8(3) . . . . no C4 C5 C6 C7 74.4(4) . . . . no C10 C5 C6 C7 -52.9(4) . . . . no C6 C5 C10 C19 -65.7(4) . . . . no C6 C5 C10 C9 57.2(3) . . . . no C4 C5 C10 C19 167.2(3) . . . . no C6 C5 C10 C1 177.8(3) . . . . no C5 C6 C7 C8 48.6(4) . . . . no C5 C6 C7 O2 -74.1(4) . . . . no O2 C7 C8 C9 71.5(3) . . . . no C6 C7 C8 C14 -175.1(3) . . . . no C6 C7 C8 C9 -50.4(3) . . . . no O2 C7 C8 C14 -53.3(3) . . . . no C9 C8 C14 C15 176.5(3) . . . . no C14 C8 C9 C10 -175.0(2) . . . . no C7 C8 C9 C11 -171.5(2) . . . . no C9 C8 C14 C13 53.4(3) . . . . no C7 C8 C14 C13 178.1(2) . . . . no C7 C8 C9 C10 59.0(3) . . . . no C14 C8 C9 C11 -45.5(3) . . . . no C7 C8 C14 C15 -58.7(4) . . . . no C10 C9 C11 C12 176.3(2) . . . . no C8 C9 C10 C19 60.1(4) . . . . no C8 C9 C11 C12 47.7(3) . . . . no C11 C9 C10 C19 -69.6(4) . . . . no C11 C9 C10 C5 168.5(2) . . . . no C8 C9 C10 C5 -61.9(3) . . . . no C11 C9 C10 C1 50.2(3) . . . . no C8 C9 C10 C1 179.9(2) . . . . no C9 C11 C12 O3 65.4(3) . . . . no C9 C11 C12 C13 -54.9(3) . . . . no O3 C12 C13 C17 50.4(3) . . . . no C11 C12 C13 C14 59.2(3) . . . . no O3 C12 C13 C14 -62.5(3) . . . . no C11 C12 C13 C18 -62.6(3) . . . . no O3 C12 C13 C18 175.8(2) . . . . no C11 C12 C13 C17 172.0(2) . . . . no C14 C13 C17 C16 -40.6(3) . . . . no C14 C13 C17 C20 -165.7(3) . . . . no C12 C13 C17 C20 77.5(3) . . . . no C18 C13 C14 C8 59.6(3) . . . . no C12 C13 C14 C8 -60.6(3) . . . . no C12 C13 C17 C16 -157.4(3) . . . . no C18 C13 C17 C16 77.3(3) . . . . no C18 C13 C17 C20 -47.9(4) . . . . no C18 C13 C14 C15 -70.8(3) . . . . no C17 C13 C14 C15 45.2(3) . . . . no C17 C13 C14 C8 175.6(2) . . . . no C12 C13 C14 C15 169.0(3) . . . . no C13 C14 C15 C16 -31.6(4) . . . . no C8 C14 C15 C16 -159.4(3) . . . . no C14 C15 C16 C17 5.4(4) . . . . no C15 C16 C17 C20 149.9(3) . . . . no C15 C16 C17 C13 22.1(4) . . . . no C13 C17 C20 C22 174.2(3) . . . . no C16 C17 C20 C21 178.5(3) . . . . no C13 C17 C20 C21 -61.8(4) . . . . no C16 C17 C20 C22 54.5(4) . . . . no C21 C20 C22 C23 70.0(4) . . . . no C17 C20 C22 C23 -164.3(3) . . . . no C20 C22 C23 C24 -179.1(3) . . . . no C22 C23 C24 O5 25.4(5) . . . . no C22 C23 C24 O4 -156.7(4) . . . . no C25 C26 C27 C28 175.6(7) . . . . no C26 C27 C28 C29 -179.1(6) . . . . no C27 C28 C29 C30 179.9(5) . . . . no C28 C29 C30 C31 -175.1(5) . . . . no C29 C30 C31 C32 -178.2(4) . . . . no C30 C31 C32 C33 -177.0(4) . . . . no C31 C32 C33 C34 -178.0(4) . . . . no C32 C33 C34 N1 70.1(5) . . . . no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag N1 H1N O1W 1.01(3) 1.78(3) 2.780(4) 170(4) 1_545 yes O1 H1O O4 0.85(7) 1.92(8) 2.749(5) 166(8) 1_556 yes O1W H1W O3 0.98(5) 2.03(7) 2.949(4) 155(5) 1_565 yes N1 H2N O4 0.99(3) 1.77(3) 2.721(4) 160(6) 1_556 yes O2 H2O O5 0.84(6) 1.91(6) 2.743(4) 171(4) 2_645 yes O1W H2W O2 0.98(4) 1.79(4) 2.763(4) 171(4) 1_565 yes N1 H3N O1 1.00(5) 1.85(5) 2.833(5) 171(4) 2_646 yes O3 H3O O5 0.82 1.97 2.779(4) 168 2_655 yes C4 H4A O2 0.97 2.42 3.086(4) 125 . yes C14 H14 O2 0.98 2.56 2.913(4) 101 . yes C14 H14 O3 0.98 2.44 2.863(4) 105 . yes C17 H17 O3 0.98 2.54 2.951(4) 105 . yes #------------------ SECTION 2. COMPOUND 2 DETAILS -------------------------# data_2 _database_code_depnum_ccdc_archive 'CCDC 636377' _audit_creation_date 2007-01-03T11:06:28-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #------------------ CHEMICAL INFORMATION ------------------------------------# _chemical_formula_moiety 'C60 H111 N1 O12' _chemical_formula_sum 'C60 H111 N O12' _chemical_formula_weight 1038.5 _chemical_absolute_configuration syn #------------------ UNIT CELL INFORMATION -----------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 18.291(7) _cell_length_b 7.973(3) _cell_length_c 20.566(7) _cell_angle_alpha 90 _cell_angle_beta 95.049(3) _cell_angle_gamma 90 _cell_volume 2987.5(19) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 8.4 _cell_measurement_theta_max 15.7 #------------------ CRYSTAL INFORMATION -------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.154 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1148 _exptl_absorpt_coefficient_mu 0.622 _exptl_absorpt_correction_type none #------------------ DATA COLLECTION INFORMATION -----------------------------# _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_probe x-ray _diffrn_measurement_device_type 'Enraf Nonius TurboCAD4' _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_measurement_method 'non-profiled omega/2theta scans' _diffrn_standards_number 3 _diffrn_standards_interval_time 120 _diffrn_standards_decay_% 4 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l -2 -2 0 2 -2 2 1 -2 2 _diffrn_reflns_number 6901 _diffrn_reflns_av_R_equivalents 0.059 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 76.42 _diffrn_reflns_theta_full 76.42 _diffrn_measured_fraction_theta_max 1 _diffrn_measured_fraction_theta_full 1 _reflns_number_total 6715 _reflns_number_gt 3461 _reflns_threshold_expression >2sigma(I) #------------------ COMPUTER PROGRAMS USED ----------------------------------# _computing_data_collection 'CAD4 Express (Enraf Nonius, 1994)' _computing_cell_refinement 'CAD4 Express (Enraf Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #------------------ REFINEMENT INFORMATION ----------------------------------# _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^)+(0.1495P)^2^+1.2844P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment calc _refine_ls_extinction_method none _refine_ls_number_reflns 6715 _refine_ls_number_parameters 618 _refine_ls_number_restraints 8 _refine_ls_R_factor_gt 0.0896 _refine_ls_wR_factor_ref 0.294 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.053 _refine_ls_shift/su_max 0.004 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.1(6) _refine_diff_density_max 0.478 _refine_diff_density_min -0.361 #------------------ ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS --------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group _atom_site_disorder_assembly C1 C 0.8677(5) 0.7804(16) 0.7299(5) 0.065(3) Uani 1 d . . . H1A H 0.9143 0.7922 0.7112 0.079 Uiso 1 calc R . . H1B H 0.8724 0.6872 0.7603 0.079 Uiso 1 calc R . . C1' C 0.9893(4) 0.9595(13) 0.3541(4) 0.048(2) Uani 1 d . . . H1'1 H 1.0258 0.949 0.3229 0.058 Uiso 1 calc R . . H1'2 H 0.9693 1.0721 0.3502 0.058 Uiso 1 calc R . . C2 C 0.8091(6) 0.7355(15) 0.6749(5) 0.063(3) Uani 1 d . . . H2A H 0.8229 0.6335 0.6533 0.075 Uiso 1 calc R . . H2B H 0.7625 0.7164 0.6926 0.075 Uiso 1 calc R . . C2' C 1.0267(4) 0.9383(12) 0.4216(5) 0.049(2) Uani 1 d . . . H2'1 H 0.9915 0.9573 0.4535 0.059 Uiso 1 calc R . . H2'2 H 1.0654 1.0212 0.4288 0.059 Uiso 1 calc R . . C3' C 1.0592(4) 0.7643(12) 0.4312(4) 0.046(2) Uani 1 d . . . H3' H 1.096 0.7487 0.3999 0.055 Uiso 1 calc R . . C3 C 0.8022(5) 0.8767(15) 0.6268(4) 0.058(3) Uani 1 d . . . H3 H 0.8486 0.8881 0.6069 0.069 Uiso 1 calc R . . C4' C 0.9990(4) 0.6330(12) 0.4171(4) 0.046(2) Uani 1 d . . . H4'1 H 1.0208 0.5222 0.4207 0.055 Uiso 1 calc R . . H4'2 H 0.9643 0.6417 0.45 0.055 Uiso 1 calc R . . C4 C 0.7856(5) 1.0396(15) 0.6587(4) 0.052(2) Uani 1 d . . . H4A H 0.7366 1.0338 0.6732 0.062 Uiso 1 calc R . . H4B H 0.7857 1.1285 0.6265 0.062 Uiso 1 calc R . . C5 C 0.8405(5) 1.0857(13) 0.7177(5) 0.054(3) Uani 1 d . . . H5 H 0.8877 1.1071 0.7002 0.065 Uiso 1 calc R . . C5' C 0.9575(4) 0.6512(13) 0.3497(4) 0.047(2) Uani 1 d . . . H5' H 0.9937 0.6318 0.3181 0.057 Uiso 1 calc R . . C6' C 0.8993(5) 0.5145(14) 0.3371(5) 0.059(3) Uani 1 d . . . H6'1 H 0.9206 0.4077 0.3512 0.071 Uiso 1 calc R . . H6'2 H 0.886 0.5074 0.2905 0.071 Uiso 1 calc R . . C6 C 0.8179(5) 1.2493(14) 0.7485(5) 0.061(3) Uani 1 d . . . H6A H 0.8035 1.3283 0.7138 0.073 Uiso 1 calc R . . H6B H 0.8604 1.2957 0.7739 0.073 Uiso 1 calc R . . C7' C 0.8291(4) 0.5425(12) 0.3718(5) 0.048(2) Uani 1 d . . . H7' H 0.7917 0.4621 0.3546 0.058 Uiso 1 calc R . . C7 C 0.7554(5) 1.2341(12) 0.7924(4) 0.047(2) Uani 1 d . . . H7 H 0.7515 1.3399 0.8161 0.057 Uiso 1 calc R . . C8' C 0.7997(4) 0.7215(11) 0.3588(4) 0.0377(18) Uani 1 d . . . H8' H 0.7843 0.7305 0.312 0.045 Uiso 1 calc R . . C8 C 0.7703(5) 1.0939(12) 0.8418(4) 0.044(2) Uani 1 d . . . H8 H 0.8146 1.1225 0.87 0.053 Uiso 1 calc R . . C9' C 0.8580(4) 0.8580(11) 0.3759(4) 0.0342(17) Uani 1 d . . . H9' H 0.8754 0.8418 0.4219 0.041 Uiso 1 calc R . . C9 C 0.7843(4) 0.9275(11) 0.8067(4) 0.0384(18) Uani 1 d . . . H9 H 0.7427 0.9117 0.7739 0.046 Uiso 1 calc R . . C10' C 0.9264(4) 0.8323(12) 0.3355(4) 0.042(2) Uani 1 d . . . C10 C 0.8538(4) 0.9413(14) 0.7686(4) 0.053(2) Uani 1 d . . . C11 C 0.7853(5) 0.7760(13) 0.8515(4) 0.050(2) Uani 1 d . . . H11A H 0.8297 0.7792 0.881 0.06 Uiso 1 calc R . . H11B H 0.7869 0.675 0.8254 0.06 Uiso 1 calc R . . C11' C 0.8267(4) 1.0339(11) 0.3701(4) 0.0379(18) Uani 1 d . . . H11C H 0.8159 1.0599 0.3242 0.046 Uiso 1 calc R . . H11D H 0.8639 1.1121 0.3877 0.046 Uiso 1 calc R . . C12 C 0.7187(4) 0.7667(12) 0.8919(4) 0.042(2) Uani 1 d . . . H12 H 0.723 0.6678 0.9203 0.05 Uiso 1 calc R . . C12' C 0.7562(4) 1.0631(10) 0.4052(3) 0.0322(16) Uani 1 d . . . H12' H 0.7367 1.1748 0.3939 0.039 Uiso 1 calc R . . C13' C 0.6979(4) 0.9301(10) 0.3827(3) 0.0301(16) Uani 1 d . . . C13 C 0.7132(4) 0.9244(12) 0.9334(4) 0.042(2) Uani 1 d . . . C14' C 0.7328(4) 0.7577(10) 0.3961(4) 0.0335(17) Uani 1 d . . . H14' H 0.749 0.7529 0.4428 0.04 Uiso 1 calc R . . C14 C 0.7062(4) 1.0737(11) 0.8852(4) 0.0380(19) Uani 1 d . . . H14 H 0.6621 1.0532 0.8557 0.046 Uiso 1 calc R . . C15 C 0.6894(6) 1.2220(13) 0.9272(5) 0.062(3) Uani 1 d . . . H15A H 0.6642 1.3096 0.9013 0.074 Uiso 1 calc R . . H15B H 0.7339 1.2678 0.9495 0.074 Uiso 1 calc R . . C15' C 0.6674(4) 0.6372(12) 0.3840(5) 0.047(2) Uani 1 d . . . H15C H 0.6601 0.6064 0.3383 0.056 Uiso 1 calc R . . H15D H 0.6754 0.5361 0.4099 0.056 Uiso 1 calc R . . C16' C 0.6017(4) 0.7341(11) 0.4046(4) 0.0399(19) Uani 1 d . . . H16A H 0.5838 0.6834 0.443 0.048 Uiso 1 calc R . . H16B H 0.5624 0.734 0.3698 0.048 Uiso 1 calc R . . C16 C 0.6380(6) 1.1445(15) 0.9774(5) 0.065(3) Uani 1 d . . . H16C H 0.6553 1.1755 1.0217 0.078 Uiso 1 calc R . . H16D H 0.5881 1.1843 0.9684 0.078 Uiso 1 calc R . . C17' C 0.6284(4) 0.9176(10) 0.4200(3) 0.0316(16) Uani 1 d . . . H17' H 0.6445 0.9222 0.4666 0.038 Uiso 1 calc R . . C17 C 0.6416(5) 0.9496(11) 0.9684(4) 0.042(2) Uani 1 d . . . H17 H 0.6004 0.9183 0.9371 0.051 Uiso 1 calc R . . C18 C 0.7809(4) 0.9400(14) 0.9829(4) 0.050(2) Uani 1 d . . . H18A H 0.7766 1.0394 1.0087 0.075 Uiso 1 calc R . . H18B H 0.8244 0.947 0.9601 0.075 Uiso 1 calc R . . H18C H 0.7839 0.8435 1.0109 0.075 Uiso 1 calc R . . C18' C 0.6745(4) 0.9584(12) 0.3093(4) 0.044(2) Uani 1 d . . . H18D H 0.6529 1.0677 0.3033 0.065 Uiso 1 calc R . . H18E H 0.6392 0.8746 0.2943 0.065 Uiso 1 calc R . . H18F H 0.7167 0.9503 0.2849 0.065 Uiso 1 calc R . . C19 C 0.9225(4) 0.9757(19) 0.8131(5) 0.075(4) Uani 1 d . . . H19A H 0.9639 0.9833 0.7876 0.112 Uiso 1 calc R . . H19B H 0.9302 0.8861 0.8441 0.112 Uiso 1 calc R . . H19C H 0.917 1.0795 0.8358 0.112 Uiso 1 calc R . . C19' C 0.9038(5) 0.8493(19) 0.2623(4) 0.073(4) Uani 1 d . . . H19D H 0.8844 0.9596 0.2533 0.109 Uiso 1 calc R . . H19E H 0.8669 0.7672 0.2494 0.109 Uiso 1 calc R . . H19F H 0.9458 0.8317 0.2383 0.109 Uiso 1 calc R . . C20' C 0.5661(4) 1.0446(11) 0.4076(4) 0.0372(18) Uani 1 d . . . H20' H 0.5498 1.0404 0.3609 0.045 Uiso 1 calc R . . C20 C 0.6318(5) 0.8553(13) 1.0316(4) 0.047(2) Uani 1 d . . . H20 H 0.6728 0.885 1.0634 0.056 Uiso 1 calc R . . C21 C 0.6326(7) 0.6656(14) 1.0222(6) 0.074(3) Uani 1 d . . . H21A H 0.6774 0.6331 1.0046 0.111 Uiso 1 calc R . . H21B H 0.5915 0.633 0.9927 0.111 Uiso 1 calc R . . H21C H 0.6294 0.6114 1.0636 0.111 Uiso 1 calc R . . C21' C 0.5906(5) 1.2221(12) 0.4231(5) 0.052(2) Uani 1 d . . . H21D H 0.6323 1.2485 0.3996 0.078 Uiso 1 calc R . . H21E H 0.6039 1.2324 0.4691 0.078 Uiso 1 calc R . . H21F H 0.5513 1.2983 0.4104 0.078 Uiso 1 calc R . . C22' C 0.5005(4) 1.0017(12) 0.4445(4) 0.0403(19) Uani 1 d . . . H22A H 0.5102 1.0388 0.4894 0.048 Uiso 1 calc R . . H22B H 0.4949 0.8807 0.4451 0.048 Uiso 1 calc R . . C22 C 0.5617(5) 0.9094(15) 1.0589(4) 0.056(3) Uani 1 d . . . H22C H 0.5205 0.8748 1.029 0.068 Uiso 1 calc R . . H22D H 0.561 1.0309 1.0613 0.068 Uiso 1 calc R . . C23 C 0.5514(6) 0.8377(14) 1.1272(4) 0.060(3) Uani 1 d . . . H23A H 0.5409 0.7187 1.1231 0.072 Uiso 1 calc R . . H23B H 0.597 0.8503 1.1546 0.072 Uiso 1 calc R . . C23' C 0.4268(4) 1.0809(11) 0.4156(4) 0.0398(19) Uani 1 d . . . H23C H 0.3911 1.0746 0.4478 0.048 Uiso 1 calc R . . H23D H 0.4347 1.1984 0.4062 0.048 Uiso 1 calc R . . C24' C 0.3970(4) 0.9943(11) 0.3549(4) 0.0361(18) Uani 1 d . . . C24 C 0.4906(5) 0.9216(14) 1.1600(5) 0.054(2) Uani 1 d . . . C25 C -0.0080(19) 0.933(6) 1.1109(18) 0.278(16) Uiso 1 d . . . C26 C 0.0066(19) 0.990(6) 1.0448(19) 0.305(19) Uiso 1 d D . . C33 C 0.3421(8) 0.812(2) 0.8229(8) 0.114(5) Uani 1 d D . . H33A H 0.3652 0.8164 0.8672 0.136 Uiso 1 calc R . . H33B H 0.3385 0.6954 0.8098 0.136 Uiso 1 calc R . . C34 C 0.3883(7) 0.9032(19) 0.7791(6) 0.094(4) Uani 1 d . . . H34A H 0.3889 1.0204 0.7919 0.113 Uiso 1 calc R . . H34B H 0.3639 0.8973 0.7353 0.113 Uiso 1 calc R . . C35 C 0.4666(7) 0.8495(18) 0.7753(6) 0.081(3) Uani 1 d . . . H35A H 0.4906 0.8483 0.8192 0.097 Uiso 1 calc R . . H35B H 0.4663 0.735 0.7592 0.097 Uiso 1 calc R . . C36 C 0.5095(7) 0.9467(16) 0.7361(7) 0.085(4) Uani 1 d . . . H36A H 0.5139 1.0585 0.7546 0.101 Uiso 1 calc R . . H36B H 0.4834 0.9567 0.6931 0.101 Uiso 1 calc R . . N1 N 0.5831(4) 0.8842(12) 0.7283(4) 0.064(2) Uani 1 d . . . H1C H 0.6058 0.9539 0.7028 0.096 Uiso 1 calc R . . H1D H 0.5801 0.7829 0.71 0.096 Uiso 1 calc R . . H1E H 0.6084 0.8777 0.7672 0.096 Uiso 1 calc R . . O1' O 1.0936(3) 0.7376(8) 0.4952(3) 0.0541(16) Uani 1 d . . . H1' H 1.0898 0.8225 0.5171 0.081 Uiso 1 calc R . . O1 O 0.7445(4) 0.8399(10) 0.5760(3) 0.068(2) Uani 1 d . . . H1 H 0.7534 0.7507 0.5584 0.102 Uiso 1 calc R . . O2' O 0.8449(3) 0.5131(8) 0.4411(3) 0.0511(15) Uani 1 d . . . H2' H 0.8605 0.4174 0.4471 0.077 Uiso 1 calc R . . O2 O 0.6863(3) 1.2000(8) 0.7570(3) 0.0497(16) Uani 1 d . . . H2 H 0.6768 1.2741 0.7299 0.074 Uiso 1 calc R . . O1W O 0.3951(4) 0.5357(10) 0.3934(3) 0.0687(19) Uani 1 d . . . O3' O 0.7718(3) 1.0530(8) 0.4741(2) 0.0389(13) Uani 1 d . . . H3'1 H 0.8156 1.0333 0.4828 0.058 Uiso 1 calc R . . O3 O 0.6546(3) 0.7514(9) 0.8470(3) 0.0602(18) Uani 1 d . . . H3A H 0.6579 0.6666 0.8248 0.09 Uiso 1 calc R . . O2W O 0.2499(4) 0.9816(16) 0.4618(4) 0.107(3) Uani 1 d . . . O4 O 0.4879(4) 0.8700(10) 1.2208(3) 0.065(2) Uani 1 d . . . O4' O 0.4153(3) 1.0487(9) 0.3008(3) 0.0527(16) Uani 1 d . . . O5' O 0.3581(4) 0.8683(9) 0.3603(3) 0.0599(18) Uani 1 d . . . O5 O 0.4485(4) 1.0187(12) 1.1338(3) 0.083(3) Uani 1 d . . . C27 C 0.0809(16) 0.923(4) 1.0398(13) 0.202(10) Uiso 1 d D . . C28 C 0.0992(19) 0.984(6) 0.9740(16) 0.267(16) Uiso 1 d D . . C29 C 0.114(2) 0.854(6) 0.9281(17) 0.304(19) Uiso 1 d D . . C30 C 0.1414(14) 0.908(4) 0.8642(12) 0.192(10) Uiso 1 d D . . C31 C 0.2133(14) 0.807(4) 0.8629(13) 0.215(11) Uiso 1 d D . . C32 C 0.2642(9) 0.888(3) 0.8213(9) 0.135(6) Uiso 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.058(6) 0.081(8) 0.062(6) 0.026(6) 0.034(5) 0.027(6) C1' 0.042(5) 0.055(6) 0.049(5) 0.013(5) 0.013(4) 0.003(4) C2 0.077(7) 0.067(7) 0.047(5) 0.007(5) 0.025(5) 0.004(6) C2' 0.028(4) 0.051(6) 0.070(6) 0.004(5) 0.010(4) -0.004(4) C3' 0.031(4) 0.052(6) 0.054(5) -0.004(5) 0.004(4) 0.009(4) C3 0.053(5) 0.085(8) 0.036(5) 0.003(5) 0.008(4) -0.004(5) C4' 0.040(4) 0.038(5) 0.059(5) -0.012(4) -0.001(4) 0.007(4) C4 0.043(4) 0.077(7) 0.036(4) 0.013(5) 0.004(4) -0.010(5) C5 0.038(5) 0.067(7) 0.060(6) 0.023(5) 0.012(4) -0.009(5) C5' 0.033(4) 0.063(6) 0.046(5) -0.018(5) 0.006(4) 0.008(4) C6' 0.057(5) 0.061(7) 0.059(6) -0.025(5) 0.006(5) 0.015(5) C6 0.070(6) 0.062(7) 0.049(5) 0.023(5) -0.001(5) -0.025(6) C7' 0.031(4) 0.042(5) 0.072(6) -0.024(5) 0.001(4) 0.000(4) C7 0.057(5) 0.046(5) 0.041(5) 0.006(4) 0.014(4) -0.018(5) C8' 0.027(4) 0.039(5) 0.047(5) -0.009(4) 0.001(3) -0.004(4) C8 0.046(5) 0.049(6) 0.037(4) 0.001(4) 0.004(4) -0.011(4) C9' 0.028(4) 0.044(5) 0.030(4) -0.002(4) 0.005(3) -0.007(4) C9 0.038(4) 0.044(5) 0.034(4) 0.009(4) 0.005(3) -0.004(4) C10' 0.033(4) 0.060(6) 0.034(4) 0.003(4) 0.005(3) 0.004(4) C10 0.035(4) 0.081(7) 0.042(5) 0.012(5) 0.005(4) 0.006(5) C11 0.052(5) 0.055(6) 0.046(5) 0.005(5) 0.019(4) -0.001(5) C11' 0.031(4) 0.040(5) 0.044(4) 0.007(4) 0.006(3) -0.003(4) C12 0.049(5) 0.042(5) 0.035(4) 0.007(4) 0.006(4) -0.004(4) C12' 0.028(3) 0.030(4) 0.038(4) 0.005(4) 0.001(3) -0.007(3) C13' 0.028(4) 0.032(4) 0.030(4) 0.001(3) 0.000(3) 0.001(3) C13 0.039(4) 0.054(5) 0.033(4) 0.002(4) 0.009(3) -0.003(4) C14' 0.026(3) 0.035(4) 0.039(4) -0.003(4) 0.004(3) 0.000(3) C14 0.038(4) 0.042(5) 0.033(4) 0.009(4) -0.002(3) -0.005(4) C15 0.088(7) 0.045(6) 0.052(6) 0.005(5) 0.009(5) 0.004(6) C15' 0.038(4) 0.038(5) 0.064(6) -0.015(5) 0.005(4) -0.010(4) C16' 0.030(4) 0.039(5) 0.050(5) 0.002(4) 0.000(3) -0.006(4) C16 0.078(7) 0.065(7) 0.054(6) 0.001(5) 0.018(5) 0.016(6) C17' 0.034(4) 0.031(4) 0.029(4) 0.002(3) 0.002(3) -0.001(3) C17 0.050(5) 0.043(5) 0.035(4) 0.003(4) 0.009(4) 0.000(4) C18 0.049(5) 0.063(6) 0.038(4) 0.002(5) -0.004(4) 0.000(5) C18' 0.036(4) 0.056(6) 0.039(4) 0.004(4) 0.000(3) 0.000(4) C19 0.033(4) 0.126(11) 0.065(6) 0.026(7) 0.000(4) -0.006(6) C19' 0.054(6) 0.128(11) 0.038(5) -0.001(6) 0.015(4) 0.011(7) C20' 0.028(4) 0.044(5) 0.041(4) -0.004(4) 0.007(3) -0.001(4) C20 0.054(5) 0.056(6) 0.031(4) 0.013(4) 0.012(4) 0.017(5) C21 0.101(9) 0.047(6) 0.081(8) 0.013(6) 0.053(7) 0.004(6) C21' 0.049(5) 0.035(5) 0.072(6) -0.001(5) 0.011(4) -0.002(4) C22' 0.037(4) 0.045(5) 0.039(4) 0.000(4) 0.005(3) -0.007(4) C22 0.062(6) 0.068(7) 0.042(5) 0.006(5) 0.021(4) 0.009(5) C23 0.076(6) 0.061(7) 0.047(5) 0.014(5) 0.023(5) 0.021(6) C23' 0.032(4) 0.049(5) 0.039(4) -0.011(4) 0.007(3) -0.003(4) C24' 0.021(3) 0.045(5) 0.043(4) -0.003(4) 0.008(3) 0.001(4) C24 0.062(6) 0.054(6) 0.050(5) 0.005(5) 0.018(4) 0.006(5) C33 0.135(12) 0.088(11) 0.126(12) -0.009(10) 0.052(10) -0.004(10) C34 0.118(11) 0.083(10) 0.080(8) 0.014(8) 0.009(8) 0.000(9) C35 0.081(8) 0.073(8) 0.093(8) -0.009(7) 0.030(7) 0.014(7) C36 0.092(9) 0.056(7) 0.110(10) 0.000(7) 0.033(8) 0.008(7) N1 0.069(5) 0.066(6) 0.057(5) -0.002(4) 0.004(4) -0.005(5) O1' 0.047(3) 0.045(4) 0.068(4) -0.009(3) -0.013(3) 0.004(3) O1 0.078(5) 0.078(5) 0.051(4) -0.002(4) 0.014(3) -0.022(4) O2' 0.049(3) 0.035(3) 0.068(4) 0.006(3) -0.001(3) 0.006(3) O2 0.049(3) 0.052(4) 0.047(3) 0.019(3) 0.001(3) -0.001(3) O1W 0.074(4) 0.071(5) 0.058(4) -0.006(4) -0.007(3) 0.015(4) O3' 0.039(3) 0.045(3) 0.032(3) -0.006(3) -0.002(2) -0.013(3) O3 0.078(4) 0.063(4) 0.040(3) 0.000(3) 0.006(3) -0.029(4) O2W 0.079(5) 0.145(10) 0.103(6) -0.007(7) 0.036(5) -0.007(6) O4 0.082(5) 0.072(5) 0.046(3) 0.012(4) 0.030(3) 0.022(4) O4' 0.068(4) 0.054(4) 0.037(3) -0.003(3) 0.012(3) -0.001(4) O5' 0.070(4) 0.056(4) 0.052(4) -0.005(3) 0.003(3) -0.020(4) O5 0.078(5) 0.110(7) 0.064(4) 0.013(5) 0.023(4) 0.047(5) #------------------ MOLECULAR GEOMETRY --------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.531(15) . ? C1 C10 1.543(16) . ? C1 H1A 0.97 . ? C1 H1B 0.97 . ? C1' C2' 1.502(12) . ? C1' C10' 1.556(12) . ? C1' H1'1 0.97 . ? C1' H1'2 0.97 . ? C2 C3 1.496(15) . ? C2 H2A 0.97 . ? C2 H2B 0.97 . ? C2' C3' 1.516(13) . ? C2' H2'1 0.97 . ? C2' H2'2 0.97 . ? C3' O1' 1.423(10) . ? C3' C4' 1.529(12) . ? C3' H3' 0.98 . ? C3 O1 1.449(11) . ? C3 C4 1.498(16) . ? C3 H3 0.98 . ? C4' C5' 1.528(12) . ? C4' H4'1 0.97 . ? C4' H4'2 0.97 . ? C4 C5 1.551(13) . ? C4 H4A 0.97 . ? C4 H4B 0.97 . ? C5 C6 1.522(15) . ? C5 C10 1.560(13) . ? C5 H5 0.98 . ? C5' C6' 1.530(14) . ? C5' C10' 1.570(13) . ? C5' H5' 0.98 . ? C6' C7' 1.539(11) . ? C6' H6'1 0.97 . ? C6' H6'2 0.97 . ? C6 C7 1.524(12) . ? C6 H6A 0.97 . ? C6 H6B 0.97 . ? C7' O2' 1.448(11) . ? C7' C8' 1.540(13) . ? C7' H7' 0.98 . ? C7 O2 1.428(10) . ? C7 C8 1.519(12) . ? C7 H7 0.98 . ? C8' C14' 1.530(10) . ? C8' C9' 1.543(10) . ? C8' H8' 0.98 . ? C8 C9 1.543(12) . ? C8 C14 1.543(11) . ? C8 H8 0.98 . ? C9' C11' 1.515(12) . ? C9' C10' 1.575(10) . ? C9' H9' 0.98 . ? C9 C11 1.519(12) . ? C9 C10 1.555(11) . ? C9 H9 0.98 . ? C10' C19' 1.532(11) . ? C10 C19 1.513(12) . ? C11 C12 1.535(11) . ? C11 H11A 0.97 . ? C11 H11B 0.97 . ? C11' C12' 1.549(10) . ? C11' H11C 0.97 . ? C11' H11D 0.97 . ? C12 O3 1.432(9) . ? C12 C13 1.528(13) . ? C12 H12 0.98 . ? C12' O3' 1.422(8) . ? C12' C13' 1.546(10) . ? C12' H12' 0.98 . ? C13' C14' 1.530(11) . ? C13' C18' 1.548(10) . ? C13' C17' 1.544(10) . ? C13 C18 1.537(11) . ? C13 C14 1.546(12) . ? C13 C17 1.563(11) . ? C14' C15' 1.537(11) . ? C14' H14' 0.98 . ? C14 C15 1.512(13) . ? C14 H14 0.98 . ? C15 C16 1.581(15) . ? C15 H15A 0.97 . ? C15 H15B 0.97 . ? C15' C16' 1.519(12) . ? C15' H15C 0.97 . ? C15' H15D 0.97 . ? C16' C17' 1.565(12) . ? C16' H16A 0.97 . ? C16' H16B 0.97 . ? C16 C17 1.567(14) . ? C16 H16C 0.97 . ? C16 H16D 0.97 . ? C17' C20' 1.529(11) . ? C17' H17' 0.98 . ? C17 C20 1.526(11) . ? C17 H17 0.98 . ? C18 H18A 0.96 . ? C18 H18B 0.96 . ? C18 H18C 0.96 . ? C18' H18D 0.96 . ? C18' H18E 0.96 . ? C18' H18F 0.96 . ? C19 H19A 0.96 . ? C19 H19B 0.96 . ? C19 H19C 0.96 . ? C19' H19D 0.96 . ? C19' H19E 0.96 . ? C19' H19F 0.96 . ? C20' C21' 1.510(12) . ? C20' C22' 1.516(10) . ? C20' H20' 0.98 . ? C20 C22 1.507(12) . ? C20 C21 1.524(15) . ? C20 H20 0.98 . ? C21 H21A 0.96 . ? C21 H21B 0.96 . ? C21 H21C 0.96 . ? C21' H21D 0.96 . ? C21' H21E 0.96 . ? C21' H21F 0.96 . ? C22' C23' 1.558(11) . ? C22' H22A 0.97 . ? C22' H22B 0.97 . ? C22 C23 1.542(12) . ? C22 H22C 0.97 . ? C22 H22D 0.97 . ? C23 C24 1.507(13) . ? C23 H23A 0.97 . ? C23 H23B 0.97 . ? C23' C24' 1.488(11) . ? C23' H23C 0.97 . ? C23' H23D 0.97 . ? C24' O5' 1.242(10) . ? C24' O4' 1.267(9) . ? C24 O5 1.188(11) . ? C24 O4 1.322(10) . ? C25 C26 1.48(4) . ? C26 C27 1.475(19) . ? C33 C34 1.479(18) . ? C33 C32 1.548(15) . ? C33 H33A 0.97 . ? C33 H33B 0.97 . ? C34 C35 1.503(17) . ? C34 H34A 0.97 . ? C34 H34B 0.97 . ? C35 C36 1.406(16) . ? C35 H35A 0.97 . ? C35 H35B 0.97 . ? C36 N1 1.457(13) . ? C36 H36A 0.97 . ? C36 H36B 0.97 . ? N1 H1C 0.89 . ? N1 H1D 0.89 . ? N1 H1E 0.89 . ? O1' H1' 0.82 . ? O1 H1 0.82 . ? O2' H2' 0.82 . ? O2 H2 0.82 . ? O3' H3'1 0.82 . ? O3 H3A 0.82 . ? C27 C28 1.505(18) . ? C28 C29 1.44(2) . ? C29 C30 1.510(19) . ? C30 C31 1.541(18) . ? C31 C32 1.468(17) . ? 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 C2 C1 C10 116.1(8) . . ? C2 C1 H1A 108.3 . . ? C10 C1 H1A 108.3 . . ? C2 C1 H1B 108.3 . . ? C10 C1 H1B 108.3 . . ? H1A C1 H1B 107.4 . . ? C2' C1' C10' 114.8(7) . . ? C2' C1' H1'1 108.6 . . ? C10' C1' H1'1 108.6 . . ? C2' C1' H1'2 108.6 . . ? C10' C1' H1'2 108.6 . . ? H1'1 C1' H1'2 107.5 . . ? C3 C2 C1 109.0(10) . . ? C3 C2 H2A 109.9 . . ? C1 C2 H2A 109.9 . . ? C3 C2 H2B 109.9 . . ? C1 C2 H2B 109.9 . . ? H2A C2 H2B 108.3 . . ? C1' C2' C3' 111.4(8) . . ? C1' C2' H2'1 109.3 . . ? C3' C2' H2'1 109.3 . . ? C1' C2' H2'2 109.3 . . ? C3' C2' H2'2 109.3 . . ? H2'1 C2' H2'2 108 . . ? O1' C3' C2' 113.2(8) . . ? O1' C3' C4' 109.0(7) . . ? C2' C3' C4' 109.5(6) . . ? O1' C3' H3' 108.3 . . ? C2' C3' H3' 108.3 . . ? C4' C3' H3' 108.3 . . ? O1 C3 C4 109.2(8) . . ? O1 C3 C2 109.8(9) . . ? C4 C3 C2 111.9(7) . . ? O1 C3 H3 108.6 . . ? C4 C3 H3 108.6 . . ? C2 C3 H3 108.6 . . ? C5' C4' C3' 113.5(8) . . ? C5' C4' H4'1 108.9 . . ? C3' C4' H4'1 108.9 . . ? C5' C4' H4'2 108.9 . . ? C3' C4' H4'2 108.9 . . ? H4'1 C4' H4'2 107.7 . . ? C3 C4 C5 113.9(8) . . ? C3 C4 H4A 108.8 . . ? C5 C4 H4A 108.8 . . ? C3 C4 H4B 108.8 . . ? C5 C4 H4B 108.8 . . ? H4A C4 H4B 107.7 . . ? C6 C5 C4 110.4(8) . . ? C6 C5 C10 112.7(8) . . ? C4 C5 C10 113.7(9) . . ? C6 C5 H5 106.5 . . ? C4 C5 H5 106.5 . . ? C10 C5 H5 106.5 . . ? C4' C5' C6' 111.6(9) . . ? C4' C5' C10' 113.5(7) . . ? C6' C5' C10' 112.8(7) . . ? C4' C5' H5' 106.1 . . ? C6' C5' H5' 106.1 . . ? C10' C5' H5' 106.1 . . ? C5' C6' C7' 114.5(7) . . ? C5' C6' H6'1 108.6 . . ? C7' C6' H6'1 108.6 . . ? C5' C6' H6'2 108.6 . . ? C7' C6' H6'2 108.6 . . ? H6'1 C6' H6'2 107.6 . . ? C5 C6 C7 115.0(8) . . ? C5 C6 H6A 108.5 . . ? C7 C6 H6A 108.5 . . ? C5 C6 H6B 108.5 . . ? C7 C6 H6B 108.5 . . ? H6A C6 H6B 107.5 . . ? O2' C7' C6' 109.3(7) . . ? O2' C7' C8' 111.0(7) . . ? C6' C7' C8' 110.2(8) . . ? O2' C7' H7' 108.8 . . ? C6' C7' H7' 108.8 . . ? C8' C7' H7' 108.8 . . ? O2 C7 C8 107.5(7) . . ? O2 C7 C6 112.9(7) . . ? C8 C7 C6 110.8(8) . . ? O2 C7 H7 108.5 . . ? C8 C7 H7 108.5 . . ? C6 C7 H7 108.5 . . ? C14' C8' C9' 108.6(6) . . ? C14' C8' C7' 111.7(7) . . ? C9' C8' C7' 113.0(6) . . ? C14' C8' H8' 107.8 . . ? C9' C8' H8' 107.8 . . ? C7' C8' H8' 107.8 . . ? C7 C8 C9 110.2(7) . . ? C7 C8 C14 111.3(7) . . ? C9 C8 C14 110.3(7) . . ? C7 C8 H8 108.3 . . ? C9 C8 H8 108.3 . . ? C14 C8 H8 108.3 . . ? C11' C9' C8' 112.7(6) . . ? C11' C9' C10' 113.1(7) . . ? C8' C9' C10' 110.6(7) . . ? C11' C9' H9' 106.6 . . ? C8' C9' H9' 106.6 . . ? C10' C9' H9' 106.6 . . ? C11 C9 C8 113.1(6) . . ? C11 C9 C10 113.3(7) . . ? C8 C9 C10 110.6(7) . . ? C11 C9 H9 106.4 . . ? C8 C9 H9 106.4 . . ? C10 C9 H9 106.4 . . ? C19' C10' C1' 108.3(8) . . ? C19' C10' C5' 109.1(8) . . ? C1' C10' C5' 107.8(6) . . ? C19' C10' C9' 110.3(6) . . ? C1' C10' C9' 112.9(7) . . ? C5' C10' C9' 108.3(7) . . ? C19 C10 C1 107.3(9) . . ? C19 C10 C9 112.3(7) . . ? C1 C10 C9 112.4(8) . . ? C19 C10 C5 110.1(9) . . ? C1 C10 C5 106.9(7) . . ? C9 C10 C5 107.7(7) . . ? C9 C11 C12 113.5(8) . . ? C9 C11 H11A 108.9 . . ? C12 C11 H11A 108.9 . . ? C9 C11 H11B 108.9 . . ? C12 C11 H11B 108.9 . . ? H11A C11 H11B 107.7 . . ? C9' C11' C12' 115.3(6) . . ? C9' C11' H11C 108.5 . . ? C12' C11' H11C 108.5 . . ? C9' C11' H11D 108.5 . . ? C12' C11' H11D 108.5 . . ? H11C C11' H11D 107.5 . . ? O3 C12 C13 109.9(7) . . ? O3 C12 C11 107.4(7) . . ? C13 C12 C11 110.8(7) . . ? O3 C12 H12 109.6 . . ? C13 C12 H12 109.6 . . ? C11 C12 H12 109.6 . . ? O3' C12' C11' 110.7(6) . . ? O3' C12' C13' 109.4(6) . . ? C11' C12' C13' 109.7(6) . . ? O3' C12' H12' 109 . . ? C11' C12' H12' 109 . . ? C13' C12' H12' 109 . . ? C14' C13' C18' 112.4(7) . . ? C14' C13' C17' 101.6(6) . . ? C18' C13' C17' 108.9(6) . . ? C14' C13' C12' 107.2(6) . . ? C18' C13' C12' 108.5(6) . . ? C17' C13' C12' 118.2(6) . . ? C12 C13 C18 110.4(7) . . ? C12 C13 C14 106.4(6) . . ? C18 C13 C14 112.3(8) . . ? C12 C13 C17 117.5(7) . . ? C18 C13 C17 110.0(6) . . ? C14 C13 C17 99.8(7) . . ? C13' C14' C8' 114.7(7) . . ? C13' C14' C15' 103.1(6) . . ? C8' C14' C15' 116.5(7) . . ? C13' C14' H14' 107.3 . . ? C8' C14' H14' 107.3 . . ? C15' C14' H14' 107.3 . . ? C15 C14 C8 116.9(8) . . ? C15 C14 C13 104.2(6) . . ? C8 C14 C13 115.2(7) . . ? C15 C14 H14 106.6 . . ? C8 C14 H14 106.6 . . ? C13 C14 H14 106.6 . . ? C14 C15 C16 103.3(8) . . ? C14 C15 H15A 111.1 . . ? C16 C15 H15A 111.1 . . ? C14 C15 H15B 111.1 . . ? C16 C15 H15B 111.1 . . ? H15A C15 H15B 109.1 . . ? C16' C15' C14' 105.1(7) . . ? C16' C15' H15C 110.7 . . ? C14' C15' H15C 110.7 . . ? C16' C15' H15D 110.7 . . ? C14' C15' H15D 110.7 . . ? H15C C15' H15D 108.8 . . ? C15' C16' C17' 106.9(6) . . ? C15' C16' H16A 110.3 . . ? C17' C16' H16A 110.3 . . ? C15' C16' H16B 110.3 . . ? C17' C16' H16B 110.3 . . ? H16A C16' H16B 108.6 . . ? C17 C16 C15 106.1(8) . . ? C17 C16 H16C 110.5 . . ? C15 C16 H16C 110.5 . . ? C17 C16 H16D 110.5 . . ? C15 C16 H16D 110.5 . . ? H16C C16 H16D 108.7 . . ? C20' C17' C13' 120.6(6) . . ? C20' C17' C16' 111.8(6) . . ? C13' C17' C16' 102.5(6) . . ? C20' C17' H17' 107.1 . . ? C13' C17' H17' 107.1 . . ? C16' C17' H17' 107.1 . . ? C20 C17 C13 119.7(7) . . ? C20 C17 C16 112.2(8) . . ? C13 C17 C16 103.2(8) . . ? C20 C17 H17 107 . . ? C13 C17 H17 107 . . ? C16 C17 H17 107 . . ? C13 C18 H18A 109.5 . . ? C13 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C13 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C13' C18' H18D 109.5 . . ? C13' C18' H18E 109.5 . . ? H18D C18' H18E 109.5 . . ? C13' C18' H18F 109.5 . . ? H18D C18' H18F 109.5 . . ? H18E C18' H18F 109.5 . . ? C10 C19 H19A 109.5 . . ? C10 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C10 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C10' C19' H19D 109.5 . . ? C10' C19' H19E 109.5 . . ? H19D C19' H19E 109.5 . . ? C10' C19' H19F 109.5 . . ? H19D C19' H19F 109.5 . . ? H19E C19' H19F 109.5 . . ? C21' C20' C22' 109.8(7) . . ? C21' C20' C17' 112.5(6) . . ? C22' C20' C17' 112.2(7) . . ? C21' C20' H20' 107.3 . . ? C22' C20' H20' 107.3 . . ? C17' C20' H20' 107.3 . . ? C22 C20 C21 110.4(9) . . ? C22 C20 C17 110.1(7) . . ? C21 C20 C17 112.2(8) . . ? C22 C20 H20 108 . . ? C21 C20 H20 108 . . ? C17 C20 H20 108 . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C20' C21' H21D 109.5 . . ? C20' C21' H21E 109.5 . . ? H21D C21' H21E 109.5 . . ? C20' C21' H21F 109.5 . . ? H21D C21' H21F 109.5 . . ? H21E C21' H21F 109.5 . . ? C20' C22' C23' 114.4(7) . . ? C20' C22' H22A 108.6 . . ? C23' C22' H22A 108.6 . . ? C20' C22' H22B 108.6 . . ? C23' C22' H22B 108.6 . . ? H22A C22' H22B 107.6 . . ? C20 C22 C23 114.2(8) . . ? C20 C22 H22C 108.7 . . ? C23 C22 H22C 108.7 . . ? C20 C22 H22D 108.7 . . ? C23 C22 H22D 108.7 . . ? H22C C22 H22D 107.6 . . ? C24 C23 C22 113.4(8) . . ? C24 C23 H23A 108.9 . . ? C22 C23 H23A 108.9 . . ? C24 C23 H23B 108.9 . . ? C22 C23 H23B 108.9 . . ? H23A C23 H23B 107.7 . . ? C24' C23' C22' 111.9(7) . . ? C24' C23' H23C 109.2 . . ? C22' C23' H23C 109.2 . . ? C24' C23' H23D 109.2 . . ? C22' C23' H23D 109.2 . . ? H23C C23' H23D 107.9 . . ? O5' C24' O4' 123.6(8) . . ? O5' C24' C23' 118.1(7) . . ? O4' C24' C23' 118.2(7) . . ? O5 C24 O4 123.7(9) . . ? O5 C24 C23 124.1(9) . . ? O4 C24 C23 112.1(9) . . ? C25 C26 C27 101(3) . . ? C34 C33 C32 111.6(14) . . ? C34 C33 H33A 109.3 . . ? C32 C33 H33A 109.3 . . ? C34 C33 H33B 109.3 . . ? C32 C33 H33B 109.3 . . ? H33A C33 H33B 108 . . ? C33 C34 C35 119.3(12) . . ? C33 C34 H34A 107.5 . . ? C35 C34 H34A 107.5 . . ? C33 C34 H34B 107.5 . . ? C35 C34 H34B 107.5 . . ? H34A C34 H34B 107 . . ? C36 C35 C34 117.1(12) . . ? C36 C35 H35A 108 . . ? C34 C35 H35A 108 . . ? C36 C35 H35B 108 . . ? C34 C35 H35B 108 . . ? H35A C35 H35B 107.3 . . ? C35 C36 N1 116.3(11) . . ? C35 C36 H36A 108.2 . . ? N1 C36 H36A 108.2 . . ? C35 C36 H36B 108.2 . . ? N1 C36 H36B 108.2 . . ? H36A C36 H36B 107.4 . . ? C36 N1 H1C 109.5 . . ? C36 N1 H1D 109.5 . . ? H1C N1 H1D 109.5 . . ? C36 N1 H1E 109.5 . . ? H1C N1 H1E 109.5 . . ? H1D N1 H1E 109.5 . . ? C3' O1' H1' 109.5 . . ? C3 O1 H1 109.5 . . ? C7' O2' H2' 109.5 . . ? C7 O2 H2 109.5 . . ? C12' O3' H3'1 109.5 . . ? C12 O3 H3A 109.5 . . ? C26 C27 C28 103(3) . . ? C29 C28 C27 115(3) . . ? C28 C29 C30 118(3) . . ? C29 C30 C31 103(2) . . ? C32 C31 C30 112(2) . . ? C31 C32 C33 116.4(18) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C13' C17' C20' C21' -60.5(9) . . . . ? C17' C20' C21' C22' -125.8(9) . . . . ? C20' C21' C22' C23' -115.4(8) . . . . ? C21' C22' C23' C24' 109.4(7) . . . . ? C13 C17 C20 C21 -60.9(12) . . . . ? C17 C20 C21 C22 -123.3(12) . . . . ? C20 C21 C22 C23 -125.5(11) . . . . ? C21 C22 C23 C24 -162.0(8) . . . . ? C13 C17 C20 C22 175.6(8) . . . . ? C17 C20 C22 C23 -172.8(9) . . . . ? C20 C22 C23 C24 167.2(9) . . . . ? C13' C17' C20' C22' 175.1(7) . . . . ? C17' C20' C22' C23' -158.2(7) . . . . ? C20' C22' C23' C24' 74.7(9) . . . . ? #------------------ SECTION 2. COMPOUND 3 DETAILS -------------------------# data_3 _database_code_depnum_ccdc_archive 'CCDC 636378' _audit_creation_date 2007-01-03T11:19:39-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #------------------ CHEMICAL INFORMATION ------------------------------------# _chemical_formula_moiety 'C38 H71 N1 O5' _chemical_formula_sum 'C38 H73 N O6' _chemical_formula_weight 639.97 _chemical_absolute_configuration syn #------------------ UNIT CELL INFORMATION -----------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 14.6044(7) _cell_length_b 7.9746(4) _cell_length_c 17.2816(7) _cell_angle_alpha 90 _cell_angle_beta 102.785(3) _cell_angle_gamma 90 _cell_volume 1962.79(16) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 18 _cell_measurement_theta_min 8.7 _cell_measurement_theta_max 19.2 #------------------ CRYSTAL INFORMATION -------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.08 _exptl_crystal_density_diffrn 1.083 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 712 _exptl_absorpt_coefficient_mu 0.556 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.83 _exptl_absorpt_correction_T_max 0.9538 #------------------ DATA COLLECTION INFORMATION -----------------------------# _diffrn_radiation_wavelength 1.54128 _diffrn_radiation_type CuK\a _diffrn_radiation_probe x-ray _diffrn_measurement_device_type 'Enraf Nonius TurboCAD4' _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_measurement_method 'non-profiled omega/2theta scans' _diffrn_standards_number 3 _diffrn_standards_interval_time 120 _diffrn_standards_decay_% 0 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l -2 2 0 -1 2 -1 0 2 2 _diffrn_reflns_number 4591 _diffrn_reflns_av_R_equivalents 0.0584 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.62 _diffrn_reflns_theta_max 76.29 _diffrn_reflns_theta_full 76.29 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measured_fraction_theta_full 0.998 _reflns_number_total 4417 _reflns_number_gt 1771 _reflns_threshold_expression >2sigma(I) #------------------ COMPUTER PROGRAMS USED ----------------------------------# _computing_data_collection 'CAD4 Express (Enraf Nonius, 1994)' _computing_cell_refinement 'CAD4 Express (Enraf Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #------------------ REFINEMENT INFORMATION ----------------------------------# _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^)+(0.0723P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 4417 _refine_ls_number_parameters 426 _refine_ls_number_restraints 6 _refine_ls_R_factor_gt 0.0725 _refine_ls_wR_factor_ref 0.191 _refine_ls_goodness_of_fit_ref 1.009 _refine_ls_restrained_S_all 1.008 _refine_ls_shift/su_max 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.3(6) _refine_diff_density_max 0.206 _refine_diff_density_min -0.275 #------------------ ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS --------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group _atom_site_disorder_assembly C1 C 0.5734(6) 0.5245(11) 0.2653(5) 0.066(3) Uani 1 d . . . H1A H 0.5342 0.5239 0.3038 0.079 Uiso 1 calc R . . H1B H 0.6102 0.6268 0.2728 0.079 Uiso 1 calc R . . C2 C 0.5111(6) 0.5249(11) 0.1826(5) 0.070(3) Uani 1 d . . . H2A H 0.4694 0.6211 0.1767 0.084 Uiso 1 calc R . . H2B H 0.5497 0.535 0.1438 0.084 Uiso 1 calc R . . C3 C 0.4536(5) 0.3667(13) 0.1669(5) 0.065(2) Uani 1 d . . . H3 H 0.4115 0.3617 0.2038 0.078 Uiso 1 calc R . . C4 C 0.5159(5) 0.2164(10) 0.1796(5) 0.053(2) Uani 1 d . . . H4A H 0.5529 0.2153 0.1393 0.063 Uiso 1 calc R . . H4B H 0.477 0.1165 0.1723 0.063 Uiso 1 calc R . . C5 C 0.5826(5) 0.2083(10) 0.2612(5) 0.051(2) Uani 1 d . . . H5 H 0.5433 0.198 0.3002 0.061 Uiso 1 calc R . . C6 C 0.6447(5) 0.0566(11) 0.2707(4) 0.053(2) Uani 1 d . . . H6A H 0.6058 -0.0412 0.2539 0.064 Uiso 1 calc R . . H6B H 0.6732 0.0428 0.3266 0.064 Uiso 1 calc R . . C7 C 0.7221(5) 0.0605(10) 0.2249(4) 0.0437(18) Uani 1 d . . . H7 H 0.764 -0.0347 0.2424 0.052 Uiso 1 calc R . . C8 C 0.7800(5) 0.2222(9) 0.2433(4) 0.0401(19) Uani 1 d . . . H8 H 0.8107 0.22 0.2998 0.048 Uiso 1 calc R . . C9 C 0.7163(4) 0.3777(10) 0.2291(4) 0.0395(16) Uani 1 d . . . H9 H 0.6816 0.371 0.1737 0.047 Uiso 1 calc R . . C10 C 0.6399(5) 0.3741(11) 0.2808(4) 0.0501(19) Uani 1 d . . . C11 C 0.7700(5) 0.5450(10) 0.2368(4) 0.048(2) Uani 1 d . . . H11A H 0.7965 0.5669 0.2924 0.057 Uiso 1 calc R . . H11B H 0.7263 0.6347 0.2168 0.057 Uiso 1 calc R . . C12 C 0.8496(5) 0.5462(10) 0.1912(4) 0.0394(18) Uani 1 d . . . H12 H 0.8863 0.649 0.2051 0.047 Uiso 1 calc R . . C13 C 0.9155(4) 0.3968(9) 0.2130(4) 0.0367(16) Uani 1 d . . . C14 C 0.8561(5) 0.2366(9) 0.1972(4) 0.0404(19) Uani 1 d . . . H14 H 0.8249 0.2375 0.1408 0.048 Uiso 1 calc R . . C15 C 0.9298(5) 0.0968(9) 0.2085(4) 0.048(2) Uani 1 d . . . H15A H 0.9059 -0.0014 0.1774 0.057 Uiso 1 calc R . . H15B H 0.9494 0.0651 0.2638 0.057 Uiso 1 calc R . . C16 C 1.0119(5) 0.1777(10) 0.1782(5) 0.059(2) Uani 1 d . . . H16A H 1.0198 0.1219 0.1302 0.071 Uiso 1 calc R . . H16B H 1.07 0.1671 0.218 0.071 Uiso 1 calc R . . C17 C 0.9879(4) 0.3658(11) 0.1611(4) 0.0426(17) Uani 1 d . . . H17 H 0.9548 0.3754 0.1054 0.051 Uiso 1 calc R . . C18 C 0.9658(4) 0.4144(10) 0.3011(3) 0.050(2) Uani 1 d . . . H18A H 1.0078 0.3215 0.3162 0.075 Uiso 1 calc R . . H18B H 0.9201 0.4154 0.3334 0.075 Uiso 1 calc R . . H18C H 1.0008 0.5172 0.3086 0.075 Uiso 1 calc R . . C19 C 0.6884(5) 0.3748(14) 0.3704(4) 0.075(2) Uani 1 d . . . H19A H 0.7307 0.2813 0.3819 0.113 Uiso 1 calc R . . H19B H 0.6416 0.366 0.4015 0.113 Uiso 1 calc R . . H19C H 0.7228 0.4773 0.3833 0.113 Uiso 1 calc R . . C20 C 1.0763(4) 0.4771(10) 0.1731(4) 0.049(2) Uani 1 d . . . H20 H 1.1049 0.4745 0.23 0.059 Uiso 1 calc R . . C21 C 1.0515(5) 0.6597(11) 0.1524(6) 0.081(3) Uani 1 d . . . H21A H 1.0047 0.6965 0.1798 0.122 Uiso 1 calc R . . H21B H 1.0275 0.6699 0.0962 0.122 Uiso 1 calc R . . H21C H 1.1067 0.7278 0.168 0.122 Uiso 1 calc R . . C22 C 1.1501(4) 0.4100(14) 0.1309(4) 0.070(3) Uani 1 d . . . H22A H 1.1672 0.2973 0.1499 0.084 Uiso 1 calc R . . H22B H 1.2059 0.4793 0.1453 0.084 Uiso 1 calc R . . C23 C 1.1191(5) 0.4050(16) 0.0401(4) 0.090(4) Uani 1 d . . . H23A H 1.0961 0.2932 0.0244 0.108 Uiso 1 calc R . . H23B H 1.0671 0.4821 0.0238 0.108 Uiso 1 calc R . . C24 C 1.1935(4) 0.4484(9) -0.0035(4) 0.0417(17) Uani 1 d . . . C25 C 0.5571(9) 0.851(3) 0.5290(10) 0.216(8) Uani 1 d . . . H25A H 0.5213 0.9092 0.5608 0.323 Uiso 1 calc R . . H25B H 0.5647 0.7358 0.5455 0.323 Uiso 1 calc R . . H25C H 0.5249 0.8559 0.4742 0.323 Uiso 1 calc R . . C26 C 0.6510(8) 0.931(2) 0.5388(9) 0.163(6) Uani 1 d . . . H26A H 0.6426 1.048 0.5237 0.196 Uiso 1 calc R . . H26B H 0.6827 0.9264 0.5943 0.196 Uiso 1 calc R . . C27 C 0.7115(7) 0.8501(16) 0.4908(5) 0.102(3) Uani 1 d . . . H27A H 0.6793 0.8548 0.4354 0.122 Uiso 1 calc R . . H27B H 0.7189 0.7328 0.5057 0.122 Uiso 1 calc R . . C28 C 0.8066(6) 0.9252(15) 0.4989(5) 0.097(3) Uani 1 d . . . H28A H 0.8395 0.9167 0.554 0.116 Uiso 1 calc R . . H28B H 0.799 1.0436 0.4861 0.116 Uiso 1 calc R . . C29 C 0.8682(6) 0.8485(13) 0.4480(4) 0.073(3) Uani 1 d . . . H29A H 0.8777 0.7309 0.4618 0.087 Uiso 1 calc R . . H29B H 0.8349 0.8542 0.3928 0.087 Uiso 1 calc R . . C30 C 0.9618(6) 0.9290(12) 0.4555(5) 0.077(3) Uani 1 d . . . H30A H 0.9939 0.9273 0.511 0.092 Uiso 1 calc R . . H30B H 0.952 1.0455 0.4398 0.092 Uiso 1 calc R . . C31 C 1.0249(6) 0.8514(12) 0.4081(4) 0.070(2) Uani 1 d . . . H31A H 1.0354 0.7354 0.4246 0.084 Uiso 1 calc R . . H31B H 0.992 0.8507 0.3528 0.084 Uiso 1 calc R . . C32 C 1.1183(6) 0.9318(12) 0.4133(4) 0.080(3) Uani 1 d . . . H32A H 1.1552 0.9187 0.467 0.096 Uiso 1 calc R . . H32B H 1.1089 1.051 0.4034 0.096 Uiso 1 calc R . . C33 C 1.1739(6) 0.8624(14) 0.3564(4) 0.083(3) Uani 1 d . . . H33A H 1.1384 0.8817 0.3026 0.1 Uiso 1 calc R . . H33B H 1.1796 0.742 0.3641 0.1 Uiso 1 calc R . . C34 C 1.2712(6) 0.9351(16) 0.3641(5) 0.101(4) Uani 1 d . . . H34A H 1.2664 1.0565 0.3625 0.122 Uiso 1 calc R . . H34B H 1.3091 0.9044 0.4156 0.122 Uiso 1 calc R . . C35 C 1.3213(5) 0.8790(17) 0.3009(4) 0.087(3) Uani 1 d . . . H35A H 1.3155 0.7582 0.2953 0.105 Uiso 1 calc R . . H35B H 1.3876 0.9049 0.3184 0.105 Uiso 1 calc R . . C36 C 1.2849(5) 0.9590(11) 0.2201(4) 0.067(2) Uani 1 d . . . H36A H 1.2169 0.953 0.2074 0.08 Uiso 1 calc R . . H36B H 1.3023 1.0766 0.2233 0.08 Uiso 1 calc R . . C37 C 1.3208(4) 0.8797(11) 0.1541(3) 0.0488(17) Uani 1 d . . . H37A H 1.3037 0.7619 0.1507 0.059 Uiso 1 calc R . . H37B H 1.3888 0.8867 0.1662 0.059 Uiso 1 calc R . . C38 C 1.2827(5) 0.9614(10) 0.0754(4) 0.056(2) Uani 1 d . . . H38A H 1.2146 0.9565 0.0636 0.067 Uiso 1 calc R . . H38B H 1.301 1.0786 0.0783 0.067 Uiso 1 calc R . . N1 N 1.3177(4) 0.8783(9) 0.0100(4) 0.0503(14) Uani 1 d D . . O1 O 0.3986(3) 0.3525(9) 0.0875(3) 0.0841(19) Uani 1 d . . . H1 H 0.3627 0.4327 0.0777 0.126 Uiso 1 calc R . . O2 O 0.6835(3) 0.0421(6) 0.1412(3) 0.0493(13) Uani 1 d . . . H2 H 0.6263 0.0327 0.1333 0.074 Uiso 1 calc R . . O1W O 1.5153(4) 0.8850(11) 0.0433(4) 0.0860(19) Uani 1 d D . . O3 O 0.8110(3) 0.5474(6) 0.1071(2) 0.0467(12) Uani 1 d . . . H3A H 0.7757 0.628 0.0957 0.07 Uiso 1 calc R . . O4 O 1.2504(3) 0.5647(7) 0.0257(3) 0.0602(14) Uani 1 d . . . O5 O 1.1992(3) 0.3685(7) -0.0638(3) 0.0580(13) Uani 1 d . . . H2N H 1.304(5) 0.756(3) 0.009(4) 0.07(2) Uiso 1 d D . . H3N H 1.3869(17) 0.895(11) 0.022(4) 0.08(2) Uiso 1 d D . . H2W H 1.553(7) 0.803(12) 0.081(5) 0.17(6) Uiso 1 d D . . H1N H 1.290(6) 0.917(14) -0.046(3) 0.15(4) Uiso 1 d D . . H1W H 1.544(6) 0.846(15) -0.001(4) 0.15(4) Uiso 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.055(5) 0.055(6) 0.095(7) -0.013(5) 0.030(5) -0.002(5) C2 0.050(5) 0.058(6) 0.101(8) 0.022(6) 0.018(5) 0.014(5) C3 0.048(4) 0.071(6) 0.078(6) 0.006(6) 0.022(4) 0.004(6) C4 0.040(4) 0.045(5) 0.079(6) 0.008(5) 0.025(4) -0.008(4) C5 0.057(5) 0.055(6) 0.048(5) 0.015(4) 0.029(4) 0.005(5) C6 0.053(4) 0.052(5) 0.057(5) 0.009(5) 0.020(4) -0.005(5) C7 0.044(4) 0.030(4) 0.058(5) 0.005(4) 0.012(4) -0.006(4) C8 0.040(4) 0.036(5) 0.043(5) 0.004(4) 0.006(4) 0.001(4) C9 0.042(4) 0.027(4) 0.051(4) 0.001(4) 0.012(3) 0.007(4) C10 0.060(4) 0.043(5) 0.054(4) -0.006(5) 0.028(4) -0.001(5) C11 0.051(5) 0.040(5) 0.054(5) -0.010(4) 0.016(4) 0.008(4) C12 0.047(4) 0.033(4) 0.035(4) 0.002(4) 0.002(3) -0.009(4) C13 0.041(3) 0.030(4) 0.036(4) -0.005(3) 0.003(3) 0.000(4) C14 0.039(4) 0.039(5) 0.045(5) 0.006(4) 0.011(4) 0.002(4) C15 0.047(4) 0.041(5) 0.055(5) 0.008(4) 0.012(4) 0.012(4) C16 0.050(4) 0.050(6) 0.079(6) 0.003(5) 0.019(4) 0.006(5) C17 0.038(3) 0.046(5) 0.041(4) 0.002(4) 0.004(3) 0.003(4) C18 0.048(4) 0.053(6) 0.047(4) 0.006(4) 0.007(3) -0.009(4) C19 0.092(6) 0.090(7) 0.054(5) -0.014(6) 0.039(4) -0.012(7) C20 0.035(4) 0.063(6) 0.045(4) -0.005(4) 0.000(3) -0.006(4) C21 0.059(5) 0.065(7) 0.123(8) 0.003(6) 0.025(6) -0.013(5) C22 0.033(4) 0.118(9) 0.059(5) -0.003(6) 0.011(3) -0.018(5) C23 0.055(4) 0.161(11) 0.058(5) -0.015(7) 0.020(4) -0.044(7) C24 0.037(4) 0.031(4) 0.054(5) -0.001(4) 0.003(3) 0.004(4) C25 0.146(11) 0.24(2) 0.286(18) 0.04(2) 0.096(13) 0.002(16) C26 0.122(10) 0.180(16) 0.207(14) -0.001(12) 0.077(10) 0.019(11) C27 0.120(8) 0.102(9) 0.080(6) 0.010(7) 0.014(6) 0.009(9) C28 0.092(7) 0.101(10) 0.096(7) 0.001(7) 0.020(6) 0.012(7) C29 0.100(6) 0.062(6) 0.054(5) 0.002(5) 0.012(5) 0.013(6) C30 0.095(6) 0.073(7) 0.063(5) -0.012(5) 0.018(5) 0.007(6) C31 0.112(7) 0.047(6) 0.054(5) 0.001(5) 0.027(5) -0.006(6) C32 0.108(7) 0.086(8) 0.048(5) 0.003(5) 0.021(5) 0.009(6) C33 0.124(8) 0.067(6) 0.061(5) 0.004(6) 0.027(5) 0.011(8) C34 0.096(7) 0.146(12) 0.061(6) -0.018(7) 0.013(5) 0.005(8) C35 0.089(6) 0.113(8) 0.058(5) -0.008(7) 0.010(5) 0.008(7) C36 0.074(5) 0.061(6) 0.069(5) -0.001(5) 0.026(5) 0.007(5) C37 0.050(4) 0.041(4) 0.054(4) -0.009(5) 0.009(3) 0.004(5) C38 0.057(4) 0.051(5) 0.057(5) -0.002(4) 0.010(4) 0.003(4) N1 0.055(4) 0.037(4) 0.059(4) 0.006(4) 0.012(3) -0.003(4) O1 0.049(3) 0.101(5) 0.096(4) 0.007(5) 0.001(3) 0.015(4) O2 0.032(2) 0.047(3) 0.066(3) -0.009(3) 0.006(2) -0.004(3) O1W 0.058(3) 0.115(6) 0.087(4) -0.025(5) 0.019(3) -0.007(5) O3 0.052(3) 0.030(3) 0.052(3) 0.006(3) -0.002(2) 0.005(3) O4 0.061(3) 0.047(3) 0.073(3) -0.007(3) 0.016(3) -0.017(3) O5 0.075(3) 0.046(3) 0.057(3) -0.012(3) 0.022(3) -0.008(3) #------------------ MOLECULAR GEOMETRY --------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.515(11) . ? C1 C10 1.529(11) . ? C1 H1A 0.97 . ? C1 H1B 0.97 . ? C2 C3 1.506(12) . ? C2 H2A 0.97 . ? C2 H2B 0.97 . ? C3 O1 1.432(8) . ? C3 C4 1.492(11) . ? C3 H3 0.98 . ? C4 C5 1.527(10) . ? C4 H4A 0.97 . ? C4 H4B 0.97 . ? C5 C6 1.499(10) . ? C5 C10 1.562(11) . ? C5 H5 0.98 . ? C6 C7 1.517(8) . ? C6 H6A 0.97 . ? C6 H6B 0.97 . ? C7 O2 1.440(7) . ? C7 C8 1.536(10) . ? C7 H7 0.98 . ? C8 C14 1.507(9) . ? C8 C9 1.538(9) . ? C8 H8 0.98 . ? C9 C11 1.539(11) . ? C9 C10 1.576(8) . ? C9 H9 0.98 . ? C10 C19 1.554(9) . ? C11 C12 1.542(9) . ? C11 H11A 0.97 . ? C11 H11B 0.97 . ? C12 O3 1.437(7) . ? C12 C13 1.525(10) . ? C12 H12 0.98 . ? C13 C14 1.535(10) . ? C13 C18 1.544(8) . ? C13 C17 1.551(8) . ? C14 C15 1.532(10) . ? C14 H14 0.98 . ? C15 C16 1.551(9) . ? C15 H15A 0.97 . ? C15 H15B 0.97 . ? C16 C17 1.554(11) . ? C16 H16A 0.97 . ? C16 H16B 0.97 . ? C17 C20 1.542(9) . ? C17 H17 0.98 . ? C18 H18A 0.96 . ? C18 H18B 0.96 . ? C18 H18C 0.96 . ? C19 H19A 0.96 . ? C19 H19B 0.96 . ? C19 H19C 0.96 . ? C20 C21 1.524(11) . ? C20 C22 1.527(9) . ? C20 H20 0.98 . ? C21 H21A 0.96 . ? C21 H21B 0.96 . ? C21 H21C 0.96 . ? C22 C23 1.534(9) . ? C22 H22A 0.97 . ? C22 H22B 0.97 . ? C23 C24 1.494(9) . ? C23 H23A 0.97 . ? C23 H23B 0.97 . ? C24 O5 1.239(7) . ? C24 O4 1.273(8) . ? C25 C26 1.487(16) . ? C25 H25A 0.96 . ? C25 H25B 0.96 . ? C25 H25C 0.96 . ? C26 C27 1.486(14) . ? C26 H26A 0.97 . ? C26 H26B 0.97 . ? C27 C28 1.491(12) . ? C27 H27A 0.97 . ? C27 H27B 0.97 . ? C28 C29 1.520(10) . ? C28 H28A 0.97 . ? C28 H28B 0.97 . ? C29 C30 1.489(10) . ? C29 H29A 0.97 . ? C29 H29B 0.97 . ? C30 C31 1.496(10) . ? C30 H30A 0.97 . ? C30 H30B 0.97 . ? C31 C32 1.492(10) . ? C31 H31A 0.97 . ? C31 H31B 0.97 . ? C32 C33 1.512(10) . ? C32 H32A 0.97 . ? C32 H32B 0.97 . ? C33 C34 1.514(11) . ? C33 H33A 0.97 . ? C33 H33B 0.97 . ? C34 C35 1.511(10) . ? C34 H34A 0.97 . ? C34 H34B 0.97 . ? C35 C36 1.520(10) . ? C35 H35A 0.97 . ? C35 H35B 0.97 . ? C36 C37 1.497(9) . ? C36 H36A 0.97 . ? C36 H36B 0.97 . ? C37 C38 1.500(8) . ? C37 H37A 0.97 . ? C37 H37B 0.97 . ? C38 N1 1.495(9) . ? C38 H38A 0.97 . ? C38 H38B 0.97 . ? N1 H2N 0.99(2) . ? N1 H3N 0.99(2) . ? N1 H1N 1.00(2) . ? O1 H1 0.82 . ? O2 H2 0.82 . ? O1W H2W 0.99(2) . ? O1W H1W 1.00(2) . ? O3 H3A 0.82 . ? 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 C2 C1 C10 113.2(7) . . ? C2 C1 H1A 108.9 . . ? C10 C1 H1A 108.9 . . ? C2 C1 H1B 108.9 . . ? C10 C1 H1B 108.9 . . ? H1A C1 H1B 107.8 . . ? C3 C2 C1 111.3(7) . . ? C3 C2 H2A 109.4 . . ? C1 C2 H2A 109.4 . . ? C3 C2 H2B 109.4 . . ? C1 C2 H2B 109.4 . . ? H2A C2 H2B 108 . . ? O1 C3 C4 105.8(7) . . ? O1 C3 C2 114.2(8) . . ? C4 C3 C2 110.4(5) . . ? O1 C3 H3 108.8 . . ? C4 C3 H3 108.8 . . ? C2 C3 H3 108.8 . . ? C3 C4 C5 114.4(7) . . ? C3 C4 H4A 108.7 . . ? C5 C4 H4A 108.7 . . ? C3 C4 H4B 108.7 . . ? C5 C4 H4B 108.7 . . ? H4A C4 H4B 107.6 . . ? C6 C5 C4 112.4(7) . . ? C6 C5 C10 112.1(6) . . ? C4 C5 C10 111.5(6) . . ? C6 C5 H5 106.8 . . ? C4 C5 H5 106.8 . . ? C10 C5 H5 106.8 . . ? C5 C6 C7 115.4(6) . . ? C5 C6 H6A 108.4 . . ? C7 C6 H6A 108.4 . . ? C5 C6 H6B 108.4 . . ? C7 C6 H6B 108.4 . . ? H6A C6 H6B 107.5 . . ? O2 C7 C6 110.5(5) . . ? O2 C7 C8 111.7(6) . . ? C6 C7 C8 110.5(6) . . ? O2 C7 H7 108 . . ? C6 C7 H7 108 . . ? C8 C7 H7 108 . . ? C14 C8 C7 113.0(6) . . ? C14 C8 C9 110.2(6) . . ? C7 C8 C9 111.0(5) . . ? C14 C8 H8 107.5 . . ? C7 C8 H8 107.5 . . ? C9 C8 H8 107.5 . . ? C8 C9 C11 114.0(5) . . ? C8 C9 C10 112.0(6) . . ? C11 C9 C10 112.2(6) . . ? C8 C9 H9 106 . . ? C11 C9 H9 106 . . ? C10 C9 H9 106 . . ? C1 C10 C19 107.7(7) . . ? C1 C10 C5 109.6(5) . . ? C19 C10 C5 108.9(7) . . ? C1 C10 C9 112.8(7) . . ? C19 C10 C9 110.0(5) . . ? C5 C10 C9 107.8(6) . . ? C9 C11 C12 112.9(6) . . ? C9 C11 H11A 109 . . ? C12 C11 H11A 109 . . ? C9 C11 H11B 109 . . ? C12 C11 H11B 109 . . ? H11A C11 H11B 107.8 . . ? O3 C12 C13 109.9(6) . . ? O3 C12 C11 110.2(5) . . ? C13 C12 C11 112.0(6) . . ? O3 C12 H12 108.2 . . ? C13 C12 H12 108.2 . . ? C11 C12 H12 108.2 . . ? C12 C13 C14 107.8(5) . . ? C12 C13 C18 108.0(6) . . ? C14 C13 C18 112.2(6) . . ? C12 C13 C17 117.1(6) . . ? C14 C13 C17 101.3(6) . . ? C18 C13 C17 110.4(5) . . ? C8 C14 C15 117.2(6) . . ? C8 C14 C13 115.1(6) . . ? C15 C14 C13 103.2(5) . . ? C8 C14 H14 106.9 . . ? C15 C14 H14 106.9 . . ? C13 C14 H14 106.9 . . ? C14 C15 C16 103.2(6) . . ? C14 C15 H15A 111.1 . . ? C16 C15 H15A 111.1 . . ? C14 C15 H15B 111.1 . . ? C16 C15 H15B 111.1 . . ? H15A C15 H15B 109.1 . . ? C15 C16 C17 107.9(6) . . ? C15 C16 H16A 110.1 . . ? C17 C16 H16A 110.1 . . ? C15 C16 H16B 110.1 . . ? C17 C16 H16B 110.1 . . ? H16A C16 H16B 108.4 . . ? C20 C17 C13 119.2(6) . . ? C20 C17 C16 112.5(5) . . ? C13 C17 C16 101.4(6) . . ? C20 C17 H17 107.7 . . ? C13 C17 H17 107.7 . . ? C16 C17 H17 107.7 . . ? C13 C18 H18A 109.5 . . ? C13 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C13 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C10 C19 H19A 109.5 . . ? C10 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C10 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C21 C20 C22 112.2(7) . . ? C21 C20 C17 111.7(6) . . ? C22 C20 C17 113.1(6) . . ? C21 C20 H20 106.4 . . ? C22 C20 H20 106.4 . . ? C17 C20 H20 106.4 . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C20 C22 C23 114.7(6) . . ? C20 C22 H22A 108.6 . . ? C23 C22 H22A 108.6 . . ? C20 C22 H22B 108.6 . . ? C23 C22 H22B 108.6 . . ? H22A C22 H22B 107.6 . . ? C24 C23 C22 115.3(6) . . ? C24 C23 H23A 108.4 . . ? C22 C23 H23A 108.4 . . ? C24 C23 H23B 108.4 . . ? C22 C23 H23B 108.4 . . ? H23A C23 H23B 107.5 . . ? O5 C24 O4 123.2(7) . . ? O5 C24 C23 119.8(7) . . ? O4 C24 C23 116.9(7) . . ? C26 C25 H25A 109.5 . . ? C26 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C26 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C27 C26 C25 113.4(14) . . ? C27 C26 H26A 108.9 . . ? C25 C26 H26A 108.9 . . ? C27 C26 H26B 108.9 . . ? C25 C26 H26B 108.9 . . ? H26A C26 H26B 107.7 . . ? C26 C27 C28 115.5(11) . . ? C26 C27 H27A 108.4 . . ? C28 C27 H27A 108.4 . . ? C26 C27 H27B 108.4 . . ? C28 C27 H27B 108.4 . . ? H27A C27 H27B 107.5 . . ? C27 C28 C29 116.3(9) . . ? C27 C28 H28A 108.2 . . ? C29 C28 H28A 108.2 . . ? C27 C28 H28B 108.2 . . ? C29 C28 H28B 108.2 . . ? H28A C28 H28B 107.4 . . ? C30 C29 C28 115.2(8) . . ? C30 C29 H29A 108.5 . . ? C28 C29 H29A 108.5 . . ? C30 C29 H29B 108.5 . . ? C28 C29 H29B 108.5 . . ? H29A C29 H29B 107.5 . . ? C29 C30 C31 116.0(7) . . ? C29 C30 H30A 108.3 . . ? C31 C30 H30A 108.3 . . ? C29 C30 H30B 108.3 . . ? C31 C30 H30B 108.3 . . ? H30A C30 H30B 107.4 . . ? C32 C31 C30 117.1(7) . . ? C32 C31 H31A 108 . . ? C30 C31 H31A 108 . . ? C32 C31 H31B 108 . . ? C30 C31 H31B 108 . . ? H31A C31 H31B 107.3 . . ? C31 C32 C33 114.7(8) . . ? C31 C32 H32A 108.6 . . ? C33 C32 H32A 108.6 . . ? C31 C32 H32B 108.6 . . ? C33 C32 H32B 108.6 . . ? H32A C32 H32B 107.6 . . ? C32 C33 C34 115.5(8) . . ? C32 C33 H33A 108.4 . . ? C34 C33 H33A 108.4 . . ? C32 C33 H33B 108.4 . . ? C34 C33 H33B 108.4 . . ? H33A C33 H33B 107.5 . . ? C35 C34 C33 114.7(8) . . ? C35 C34 H34A 108.6 . . ? C33 C34 H34A 108.6 . . ? C35 C34 H34B 108.6 . . ? C33 C34 H34B 108.6 . . ? H34A C34 H34B 107.6 . . ? C34 C35 C36 114.4(8) . . ? C34 C35 H35A 108.7 . . ? C36 C35 H35A 108.7 . . ? C34 C35 H35B 108.7 . . ? C36 C35 H35B 108.7 . . ? H35A C35 H35B 107.6 . . ? C37 C36 C35 114.3(7) . . ? C37 C36 H36A 108.7 . . ? C35 C36 H36A 108.7 . . ? C37 C36 H36B 108.7 . . ? C35 C36 H36B 108.7 . . ? H36A C36 H36B 107.6 . . ? C36 C37 C38 112.6(6) . . ? C36 C37 H37A 109.1 . . ? C38 C37 H37A 109.1 . . ? C36 C37 H37B 109.1 . . ? C38 C37 H37B 109.1 . . ? H37A C37 H37B 107.8 . . ? N1 C38 C37 111.9(6) . . ? N1 C38 H38A 109.2 . . ? C37 C38 H38A 109.2 . . ? N1 C38 H38B 109.2 . . ? C37 C38 H38B 109.2 . . ? H38A C38 H38B 107.9 . . ? C38 N1 H2N 110(4) . . ? C38 N1 H3N 107(4) . . ? H2N N1 H3N 109(7) . . ? C38 N1 H1N 117(6) . . ? H2N N1 H1N 104(8) . . ? H3N N1 H1N 109(7) . . ? C3 O1 H1 109.5 . . ? C7 O2 H2 109.5 . . ? H2W O1W H1W 92(9) . . ? C12 O3 H3A 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C13 C17 C20 C22 168.0(6) . . . . ? C17 C20 C22 C23 64.0(10) . . . . ? C20 C22 C23 C24 142.4(8) . . . . ? C13 C17 C20 C21 -64.2(9) . . . . ? C13 C17 C20 C22 168.0(6) . . . . ? C17 C20 C22 C23 64.0(10) . . . . ? C20 C22 C23 C24 142.4(8) . . . . ? C13 C17 C20 C21 -64.2(9) . . . . ? C20 C21 C22 C23 125.0(8) . . . . ? C21 C22 C23 C24 112.3(8) . . . . ? #------------------ SECTION 2. COMPOUND(S) DETAILS -------------------------# data_4 _database_code_depnum_ccdc_archive 'CCDC 636379' _audit_creation_date 2007-01-03T11:59:46-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #------------------ CHEMICAL INFORMATION ------------------------------------# _chemical_formula_moiety 'C40 H78 N1 O5' _chemical_formula_sum 'C40 H77 N O6' _chemical_formula_weight 668.03 _chemical_absolute_configuration syn #------------------ UNIT CELL INFORMATION -----------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 14.593(4) _cell_length_b 7.990(2) _cell_length_c 18.702(8) _cell_angle_alpha 90 _cell_angle_beta 109.52(3) _cell_angle_gamma 90 _cell_volume 2055.3(12) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 10 _cell_measurement_theta_max 18 #------------------ CRYSTAL INFORMATION -------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.079 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 744 _exptl_absorpt_coefficient_mu 0.549 _exptl_absorpt_correction_type none #------------------ DATA COLLECTION INFORMATION -----------------------------# _diffrn_radiation_wavelength 1.5412 _diffrn_radiation_type CuK\a _diffrn_radiation_probe x-ray _diffrn_measurement_device_type 'Enraf Nonius TurboCAD4' _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_measurement_method 'non-profiled omega/2theta scans' _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_interval_time 120 _diffrn_standards_decay_% 4 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l -2 -2 0 1 -2 1 0 -2 2 _diffrn_reflns_number 4764 _diffrn_reflns_av_R_equivalents 0.0443 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.51 _diffrn_reflns_theta_max 76.81 _diffrn_reflns_theta_full 76.81 _diffrn_measured_fraction_theta_max 0.992 _diffrn_measured_fraction_theta_full 0.992 _reflns_number_total 4624 _reflns_number_gt 2175 _reflns_threshold_expression >2sigma(I) #------------------ COMPUTER PROGRAMS USED ----------------------------------# _computing_data_collection 'CAD4 Express (Enraf Nonius, 1994)' _computing_cell_refinement 'CAD4 Express (Enraf Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #------------------ REFINEMENT INFORMATION ----------------------------------# _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^)+(0.0874P)^2^+0.9441P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 4624 _refine_ls_number_parameters 444 _refine_ls_number_restraints 6 _refine_ls_R_factor_gt 0.0726 _refine_ls_wR_factor_ref 0.2303 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.036 _refine_ls_shift/su_max 0.003 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.0(7) _refine_diff_density_max 0.224 _refine_diff_density_min -0.33 #------------------ ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS --------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group _atom_site_disorder_assembly C1 C 0.1123(7) 1.0158(11) 0.2530(6) 0.074(3) Uani 1 d . . . H1A H 0.1499 1.1184 0.261 0.089 Uiso 1 calc R . . H1B H 0.0783 1.0136 0.2896 0.089 Uiso 1 calc R . . C2 C 0.0372(6) 1.0189(11) 0.1732(6) 0.079(3) Uani 1 d . . . H2A H -0.0048 1.1156 0.1678 0.095 Uiso 1 calc R . . H2B H 0.07 1.028 0.136 0.095 Uiso 1 calc R . . C3 C -0.0224(5) 0.8627(12) 0.1593(5) 0.070(2) Uani 1 d . . . H3 H -0.0595 0.8591 0.1943 0.084 Uiso 1 calc R . . C4 C 0.0418(5) 0.7115(9) 0.1717(5) 0.061(2) Uani 1 d . . . H4A H 0.0728 0.7096 0.1332 0.073 Uiso 1 calc R . . H4B H 0.0017 0.6121 0.165 0.073 Uiso 1 calc R . . C5 C 0.1196(6) 0.7041(9) 0.2489(5) 0.056(2) Uani 1 d . . . H5 H 0.086 0.6945 0.2862 0.067 Uiso 1 calc R . . C6 C 0.1823(5) 0.5484(10) 0.2574(4) 0.062(2) Uani 1 d . . . H6A H 0.14 0.4526 0.2395 0.074 Uiso 1 calc R . . H6B H 0.2177 0.5312 0.3108 0.074 Uiso 1 calc R . . C7 C 0.2552(5) 0.5544(10) 0.2148(4) 0.0558(18) Uani 1 d . . . H7 H 0.2997 0.4592 0.2314 0.067 Uiso 1 calc R . . C8 C 0.3155(5) 0.7163(8) 0.2321(4) 0.0460(17) Uani 1 d . . . H8 H 0.3548 0.7137 0.286 0.055 Uiso 1 calc R . . C9 C 0.2500(4) 0.8725(10) 0.2195(4) 0.0475(15) Uani 1 d . . . H9 H 0.2071 0.8663 0.1665 0.057 Uiso 1 calc R . . C10 C 0.1814(5) 0.8686(10) 0.2681(4) 0.0591(18) Uani 1 d . . . C11 C 0.3052(5) 1.0358(9) 0.2260(4) 0.0552(19) Uani 1 d . . . H11A H 0.2585 1.1255 0.2073 0.066 Uiso 1 calc R . . H11B H 0.3399 1.0574 0.2792 0.066 Uiso 1 calc R . . C12 C 0.3775(5) 1.0413(8) 0.1835(4) 0.0477(17) Uani 1 d . . . H12 H 0.416 1.144 0.1976 0.057 Uiso 1 calc R . . C13 C 0.4463(4) 0.8910(9) 0.2044(3) 0.0467(16) Uani 1 d . . . C14 C 0.3852(5) 0.7306(8) 0.1877(4) 0.0446(17) Uani 1 d . . . H14 H 0.346 0.7324 0.1338 0.054 Uiso 1 calc R . . C15 C 0.4611(5) 0.5916(8) 0.1989(5) 0.0559(19) Uani 1 d . . . H15A H 0.4325 0.4927 0.1699 0.067 Uiso 1 calc R . . H15B H 0.4893 0.5616 0.252 0.067 Uiso 1 calc R . . C16 C 0.5378(5) 0.6701(9) 0.1691(5) 0.062(2) Uani 1 d . . . H16A H 0.5368 0.6156 0.1226 0.074 Uiso 1 calc R . . H16B H 0.6022 0.6577 0.2063 0.074 Uiso 1 calc R . . C17 C 0.5118(5) 0.8589(10) 0.1544(4) 0.0525(17) Uani 1 d . . . H17 H 0.4701 0.8694 0.1013 0.063 Uiso 1 calc R . . C18 C 0.5097(5) 0.9065(10) 0.2879(3) 0.062(2) Uani 1 d . . . H18A H 0.5465 1.0085 0.2953 0.093 Uiso 1 calc R . . H18B H 0.5534 0.813 0.3019 0.093 Uiso 1 calc R . . H18C H 0.469 0.9078 0.319 0.093 Uiso 1 calc R . . C19 C 0.2413(6) 0.8724(14) 0.3536(4) 0.081(2) Uani 1 d . . . H19A H 0.2861 0.7803 0.3656 0.122 Uiso 1 calc R . . H19B H 0.1984 0.8637 0.3826 0.122 Uiso 1 calc R . . H19C H 0.2768 0.9757 0.3655 0.122 Uiso 1 calc R . . C20 C 0.6000(5) 0.9702(10) 0.1651(4) 0.061(2) Uani 1 d . . . H20 H 0.6377 0.9684 0.2194 0.073 Uiso 1 calc R . . C21 C 0.5725(6) 1.1525(11) 0.1447(6) 0.089(3) Uani 1 d . . . H21A H 0.5298 1.1902 0.1708 0.134 Uiso 1 calc R . . H21B H 0.5402 1.162 0.0909 0.134 Uiso 1 calc R . . H21C H 0.6302 1.2201 0.1595 0.134 Uiso 1 calc R . . C22 C 0.6680(5) 0.9072(12) 0.1238(4) 0.071(3) Uani 1 d . . . H22A H 0.7243 0.9802 0.1369 0.085 Uiso 1 calc R . . H22B H 0.6908 0.7965 0.143 0.085 Uiso 1 calc R . . C23 C 0.6252(5) 0.8973(17) 0.0384(4) 0.094(3) Uani 1 d . . . H23A H 0.6019 0.7842 0.0243 0.113 Uiso 1 calc R . . H23B H 0.5696 0.9716 0.0214 0.113 Uiso 1 calc R . . C24 C 0.6946(5) 0.9424(9) -0.0025(4) 0.0507(17) Uani 1 d . . . C25 C 0.0113(16) 0.358(4) 0.5755(11) 0.282(12) Uani 1 d . . . H25A H -0.0104 0.4103 0.6132 0.422 Uiso 1 calc R . . H25B H 0.0219 0.2408 0.5866 0.422 Uiso 1 calc R . . H25C H -0.0372 0.3718 0.5264 0.422 Uiso 1 calc R . . C26 C 0.0971(13) 0.431(3) 0.5758(14) 0.259(13) Uani 1 d . . . H26A H 0.1453 0.4193 0.6259 0.31 Uiso 1 calc R . . H26B H 0.0863 0.5499 0.5655 0.31 Uiso 1 calc R . . C28 C 0.1363(11) 0.354(2) 0.5173(7) 0.149(5) Uani 1 d . . . H28A H 0.1428 0.2343 0.5259 0.179 Uiso 1 calc R . . H28B H 0.0891 0.3718 0.4672 0.179 Uiso 1 calc R . . C29 C 0.2289(9) 0.4202(19) 0.5185(7) 0.138(5) Uani 1 d . . . H29A H 0.2726 0.4158 0.5705 0.166 Uiso 1 calc R . . H29B H 0.2194 0.5374 0.5045 0.166 Uiso 1 calc R . . C31 C 0.2798(9) 0.3418(16) 0.4703(5) 0.112(4) Uani 1 d . . . H31A H 0.2381 0.3499 0.4177 0.134 Uiso 1 calc R . . H31B H 0.2888 0.2239 0.483 0.134 Uiso 1 calc R . . C32 C 0.3780(8) 0.4168(15) 0.4773(6) 0.107(3) Uani 1 d . . . H32A H 0.3689 0.5349 0.4649 0.128 Uiso 1 calc R . . H32B H 0.4196 0.4083 0.5298 0.128 Uiso 1 calc R . . C33 C 0.4298(8) 0.3394(14) 0.4287(5) 0.095(3) Uani 1 d . . . H33A H 0.4405 0.2218 0.4416 0.114 Uiso 1 calc R . . H33B H 0.3883 0.3464 0.376 0.114 Uiso 1 calc R . . C34 C 0.5254(8) 0.4190(13) 0.4364(5) 0.100(3) Uani 1 d . . . H34A H 0.5658 0.4152 0.4894 0.12 Uiso 1 calc R . . H34B H 0.514 0.536 0.4223 0.12 Uiso 1 calc R . . C35 C 0.5814(8) 0.3429(13) 0.3905(5) 0.097(3) Uani 1 d . . . H35A H 0.5945 0.227 0.406 0.116 Uiso 1 calc R . . H35B H 0.5397 0.3425 0.3378 0.116 Uiso 1 calc R . . C36 C 0.6744(8) 0.4219(14) 0.3945(5) 0.102(3) Uani 1 d . . . H36A H 0.7201 0.4061 0.4453 0.122 Uiso 1 calc R . . H36B H 0.6637 0.5414 0.3867 0.122 Uiso 1 calc R . . C37 C 0.7206(8) 0.3591(15) 0.3391(5) 0.100(3) Uani 1 d . . . H37A H 0.6766 0.3823 0.2883 0.119 Uiso 1 calc R . . H37B H 0.7266 0.2385 0.3443 0.119 Uiso 1 calc R . . C38 C 0.8187(8) 0.4292(17) 0.3458(6) 0.124(4) Uani 1 d . . . H38A H 0.8641 0.399 0.3951 0.148 Uiso 1 calc R . . H38B H 0.814 0.5503 0.344 0.148 Uiso 1 calc R . . C39 C 0.8611(7) 0.3721(18) 0.2853(5) 0.103(3) Uani 1 d . . . H39A H 0.9302 0.3965 0.3027 0.124 Uiso 1 calc R . . H39B H 0.8535 0.2518 0.2792 0.124 Uiso 1 calc R . . C40 C 0.8138(6) 0.4549(11) 0.2086(4) 0.077(2) Uani 1 d . . . H40A H 0.7437 0.4503 0.1959 0.093 Uiso 1 calc R . . H40B H 0.8327 0.5718 0.2123 0.093 Uiso 1 calc R . . C41 C 0.8410(5) 0.3743(11) 0.1456(4) 0.0611(18) Uani 1 d . . . H41A H 0.9109 0.3812 0.1574 0.073 Uiso 1 calc R . . H41B H 0.8233 0.2568 0.1423 0.073 Uiso 1 calc R . . C42 C 0.7919(5) 0.4556(10) 0.0706(4) 0.0617(19) Uani 1 d . . . H42A H 0.8101 0.5727 0.0734 0.074 Uiso 1 calc R . . H42B H 0.722 0.4495 0.0587 0.074 Uiso 1 calc R . . N1 N 0.8192(4) 0.3724(9) 0.0088(3) 0.0581(14) Uani 1 d D . . O1 O -0.0879(4) 0.8484(9) 0.0831(3) 0.0874(17) Uani 1 d . . . H1 H -0.1252 0.9285 0.0733 0.131 Uiso 1 calc R . . O2 O 0.2034(3) 0.5366(6) 0.1349(3) 0.0577(13) Uani 1 d . . . H2 H 0.1451 0.5265 0.1279 0.087 Uiso 1 calc R . . O1W O 0.0221(4) 0.3747(12) 0.0422(4) 0.0933(18) Uani 1 d D . . O3 O 0.3273(3) 1.0431(6) 0.1033(2) 0.0565(12) Uani 1 d . . . H3A H 0.2685 1.0411 0.0951 0.085 Uiso 1 calc R . . O4 O 0.7542(4) 1.0594(6) 0.0248(3) 0.0671(14) Uani 1 d . . . O5 O 0.6895(3) 0.8655(7) -0.0611(3) 0.0669(13) Uani 1 d . . . H1N H 0.800(4) 0.253(3) 0.009(3) 0.044(17) Uiso 1 d D . . H1W H 0.023(7) 0.492(4) 0.027(5) 0.10(4) Uiso 1 d D . . H2N H 0.783(4) 0.421(9) -0.041(2) 0.08(2) Uiso 1 d D . . H2W H 0.037(8) 0.351(18) -0.005(4) 0.16(4) Uiso 1 d D . . H3N H 0.889(2) 0.380(16) 0.015(5) 0.14(4) Uiso 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.081(6) 0.052(5) 0.107(7) -0.007(5) 0.055(6) 0.005(5) C2 0.071(6) 0.061(6) 0.121(8) 0.018(6) 0.053(6) 0.028(5) C3 0.060(4) 0.068(5) 0.089(6) 0.018(6) 0.034(4) 0.008(5) C4 0.055(5) 0.049(5) 0.085(6) 0.010(4) 0.035(5) -0.005(4) C5 0.066(5) 0.050(5) 0.065(5) 0.009(4) 0.040(4) -0.003(4) C6 0.065(5) 0.048(4) 0.077(5) 0.018(4) 0.031(4) -0.004(4) C7 0.065(4) 0.041(4) 0.065(5) 0.010(4) 0.026(4) 0.004(4) C8 0.049(4) 0.037(4) 0.053(4) 0.006(3) 0.019(4) -0.002(3) C9 0.052(4) 0.038(3) 0.058(4) 0.006(4) 0.025(3) -0.001(4) C10 0.080(5) 0.044(4) 0.063(4) -0.004(4) 0.037(4) 0.001(5) C11 0.061(5) 0.044(4) 0.061(5) -0.007(4) 0.022(4) 0.001(4) C12 0.057(4) 0.030(3) 0.058(5) 0.002(3) 0.022(4) -0.005(3) C13 0.051(4) 0.040(4) 0.046(4) 0.005(3) 0.013(3) 0.001(3) C14 0.054(4) 0.033(4) 0.050(4) 0.005(3) 0.021(4) 0.000(3) C15 0.055(4) 0.036(4) 0.080(5) 0.011(4) 0.027(4) 0.014(3) C16 0.055(4) 0.051(5) 0.087(6) -0.001(4) 0.034(4) 0.010(4) C17 0.049(4) 0.051(4) 0.056(4) 0.001(4) 0.015(3) -0.008(4) C18 0.062(4) 0.065(5) 0.054(4) -0.002(4) 0.013(3) -0.015(4) C19 0.098(6) 0.093(6) 0.063(4) -0.014(6) 0.040(4) -0.017(6) C20 0.052(4) 0.068(5) 0.065(5) -0.001(4) 0.022(4) -0.012(4) C21 0.067(6) 0.062(6) 0.141(9) 0.001(6) 0.037(6) -0.017(5) C22 0.054(4) 0.092(7) 0.069(5) -0.003(5) 0.025(4) -0.026(5) C23 0.064(5) 0.154(10) 0.071(5) -0.024(7) 0.033(4) -0.037(7) C24 0.053(4) 0.035(4) 0.065(5) 0.000(4) 0.021(4) -0.004(3) C25 0.28(2) 0.32(3) 0.29(2) 0.03(3) 0.16(2) 0.09(3) C26 0.207(19) 0.21(2) 0.45(4) -0.04(2) 0.23(2) 0.007(18) C28 0.165(12) 0.150(13) 0.144(10) 0.009(11) 0.067(10) 0.012(13) C29 0.137(10) 0.136(13) 0.152(11) -0.013(10) 0.064(9) 0.016(10) C31 0.161(10) 0.101(9) 0.080(6) 0.021(7) 0.049(7) 0.009(9) C32 0.134(9) 0.098(9) 0.089(7) -0.004(6) 0.037(7) 0.007(8) C33 0.129(8) 0.074(7) 0.077(6) 0.006(5) 0.028(6) 0.004(7) C34 0.151(9) 0.075(7) 0.076(6) -0.006(5) 0.040(6) -0.003(7) C35 0.158(10) 0.067(6) 0.073(6) 0.003(5) 0.048(6) 0.002(7) C36 0.125(8) 0.099(8) 0.084(6) -0.006(6) 0.038(6) 0.001(7) C37 0.136(8) 0.088(7) 0.076(6) 0.001(6) 0.037(6) 0.014(8) C38 0.125(9) 0.150(13) 0.087(7) -0.023(8) 0.024(6) -0.009(9) C39 0.106(7) 0.122(8) 0.076(6) 0.006(7) 0.024(5) 0.023(8) C40 0.096(6) 0.067(5) 0.071(5) -0.005(5) 0.030(5) 0.003(5) C41 0.065(4) 0.048(4) 0.073(5) -0.012(5) 0.027(4) -0.007(4) C42 0.069(5) 0.051(4) 0.064(5) 0.000(4) 0.020(4) -0.002(4) N1 0.062(4) 0.046(4) 0.064(4) -0.003(4) 0.019(3) -0.009(4) O1 0.061(3) 0.091(5) 0.106(4) 0.009(4) 0.022(3) 0.017(4) O2 0.049(3) 0.052(3) 0.076(3) -0.007(3) 0.026(2) -0.010(3) O1W 0.076(4) 0.104(5) 0.105(5) -0.018(5) 0.037(3) -0.025(5) O3 0.052(3) 0.051(3) 0.061(3) 0.010(3) 0.011(2) -0.002(3) O4 0.077(3) 0.048(3) 0.081(3) -0.004(3) 0.033(3) -0.015(3) O5 0.083(3) 0.051(3) 0.072(3) -0.011(3) 0.033(3) -0.006(3) #------------------ MOLECULAR GEOMETRY --------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C10 1.513(11) . ? C1 C2 1.530(12) . ? C1 H1A 0.97 . ? C1 H1B 0.97 . ? C2 C3 1.493(12) . ? C2 H2A 0.97 . ? C2 H2B 0.97 . ? C3 O1 1.430(9) . ? C3 C4 1.499(11) . ? C3 H3 0.98 . ? C4 C5 1.510(11) . ? C4 H4A 0.97 . ? C4 H4B 0.97 . ? C5 C6 1.521(10) . ? C5 C10 1.566(10) . ? C5 H5 0.98 . ? C6 C7 1.527(9) . ? C6 H6A 0.97 . ? C6 H6B 0.97 . ? C7 O2 1.439(8) . ? C7 C8 1.537(10) . ? C7 H7 0.98 . ? C8 C14 1.516(9) . ? C8 C9 1.541(9) . ? C8 H8 0.98 . ? C9 C11 1.516(10) . ? C9 C10 1.563(8) . ? C9 H9 0.98 . ? C10 C19 1.545(9) . ? C11 C12 1.519(10) . ? C11 H11A 0.97 . ? C11 H11B 0.97 . ? C12 O3 1.432(8) . ? C12 C13 1.530(9) . ? C12 H12 0.98 . ? C13 C14 1.532(9) . ? C13 C18 1.533(8) . ? C13 C17 1.565(9) . ? C14 C15 1.533(9) . ? C14 H14 0.98 . ? C15 C16 1.540(10) . ? C15 H15A 0.97 . ? C15 H15B 0.97 . ? C16 C17 1.557(11) . ? C16 H16A 0.97 . ? C16 H16B 0.97 . ? C17 C20 1.522(9) . ? C17 H17 0.98 . ? C18 H18A 0.96 . ? C18 H18B 0.96 . ? C18 H18C 0.96 . ? C19 H19A 0.96 . ? C19 H19B 0.96 . ? C19 H19C 0.96 . ? C20 C21 1.525(12) . ? C20 C22 1.532(10) . ? C20 H20 0.98 . ? C21 H21A 0.96 . ? C21 H21B 0.96 . ? C21 H21C 0.96 . ? C22 C23 1.512(9) . ? C22 H22A 0.97 . ? C22 H22B 0.97 . ? C23 C24 1.502(9) . ? C23 H23A 0.97 . ? C23 H23B 0.97 . ? C24 O5 1.237(8) . ? C24 O4 1.263(8) . ? C25 C26 1.38(3) . ? C25 H25A 0.96 . ? C25 H25B 0.96 . ? C25 H25C 0.96 . ? C26 C28 1.52(2) . ? C26 H26A 0.97 . ? C26 H26B 0.97 . ? C28 C29 1.445(15) . ? C28 H28A 0.97 . ? C28 H28B 0.97 . ? C29 C31 1.484(14) . ? C29 H29A 0.97 . ? C29 H29B 0.97 . ? C31 C32 1.518(13) . ? C31 H31A 0.97 . ? C31 H31B 0.97 . ? C32 C33 1.497(12) . ? C32 H32A 0.97 . ? C32 H32B 0.97 . ? C33 C34 1.496(12) . ? C33 H33A 0.97 . ? C33 H33B 0.97 . ? C34 C35 1.498(12) . ? C34 H34A 0.97 . ? C34 H34B 0.97 . ? C35 C36 1.477(12) . ? C35 H35A 0.97 . ? C35 H35B 0.97 . ? C36 C37 1.498(12) . ? C36 H36A 0.97 . ? C36 H36B 0.97 . ? C37 C38 1.504(13) . ? C37 H37A 0.97 . ? C37 H37B 0.97 . ? C38 C39 1.529(12) . ? C38 H38A 0.97 . ? C38 H38B 0.97 . ? C39 C40 1.519(11) . ? C39 H39A 0.97 . ? C39 H39B 0.97 . ? C40 C41 1.508(9) . ? C40 H40A 0.97 . ? C40 H40B 0.97 . ? C41 C42 1.493(9) . ? C41 H41A 0.97 . ? C41 H41B 0.97 . ? C42 N1 1.497(9) . ? C42 H42A 0.97 . ? C42 H42B 0.97 . ? N1 H1N 1.00(2) . ? N1 H2N 0.99(2) . ? N1 H3N 0.99(2) . ? O1 H1 0.82 . ? O2 H2 0.82 . ? O1W H1W 0.98(2) . ? O1W H2W 1.00(2) . ? O3 H3A 0.82 . ? 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 C10 C1 C2 114.2(7) . . ? C10 C1 H1A 108.7 . . ? C2 C1 H1A 108.7 . . ? C10 C1 H1B 108.7 . . ? C2 C1 H1B 108.7 . . ? H1A C1 H1B 107.6 . . ? C3 C2 C1 110.0(7) . . ? C3 C2 H2A 109.7 . . ? C1 C2 H2A 109.7 . . ? C3 C2 H2B 109.7 . . ? C1 C2 H2B 109.7 . . ? H2A C2 H2B 108.2 . . ? O1 C3 C2 113.4(7) . . ? O1 C3 C4 105.4(7) . . ? C2 C3 C4 110.4(5) . . ? O1 C3 H3 109.2 . . ? C2 C3 H3 109.2 . . ? C4 C3 H3 109.2 . . ? C3 C4 C5 114.3(7) . . ? C3 C4 H4A 108.7 . . ? C5 C4 H4A 108.7 . . ? C3 C4 H4B 108.7 . . ? C5 C4 H4B 108.7 . . ? H4A C4 H4B 107.6 . . ? C4 C5 C6 111.5(6) . . ? C4 C5 C10 112.2(6) . . ? C6 C5 C10 112.5(6) . . ? C4 C5 H5 106.8 . . ? C6 C5 H5 106.8 . . ? C10 C5 H5 106.8 . . ? C5 C6 C7 114.8(6) . . ? C5 C6 H6A 108.6 . . ? C7 C6 H6A 108.6 . . ? C5 C6 H6B 108.6 . . ? C7 C6 H6B 108.6 . . ? H6A C6 H6B 107.5 . . ? O2 C7 C6 108.8(6) . . ? O2 C7 C8 111.5(6) . . ? C6 C7 C8 111.5(6) . . ? O2 C7 H7 108.3 . . ? C6 C7 H7 108.3 . . ? C8 C7 H7 108.3 . . ? C14 C8 C7 113.0(6) . . ? C14 C8 C9 110.5(5) . . ? C7 C8 C9 111.6(5) . . ? C14 C8 H8 107.2 . . ? C7 C8 H8 107.2 . . ? C9 C8 H8 107.2 . . ? C11 C9 C8 113.5(5) . . ? C11 C9 C10 113.4(6) . . ? C8 C9 C10 112.3(6) . . ? C11 C9 H9 105.6 . . ? C8 C9 H9 105.6 . . ? C10 C9 H9 105.6 . . ? C1 C10 C19 106.8(7) . . ? C1 C10 C9 113.1(6) . . ? C19 C10 C9 110.5(6) . . ? C1 C10 C5 108.2(6) . . ? C19 C10 C5 109.7(7) . . ? C9 C10 C5 108.4(6) . . ? C12 C11 C9 115.2(6) . . ? C12 C11 H11A 108.5 . . ? C9 C11 H11A 108.5 . . ? C12 C11 H11B 108.5 . . ? C9 C11 H11B 108.5 . . ? H11A C11 H11B 107.5 . . ? O3 C12 C11 110.3(6) . . ? O3 C12 C13 109.7(5) . . ? C11 C12 C13 110.8(5) . . ? O3 C12 H12 108.7 . . ? C11 C12 H12 108.7 . . ? C13 C12 H12 108.7 . . ? C14 C13 C12 108.5(5) . . ? C14 C13 C18 112.8(6) . . ? C12 C13 C18 108.5(6) . . ? C14 C13 C17 99.9(5) . . ? C12 C13 C17 117.1(6) . . ? C18 C13 C17 109.9(5) . . ? C8 C14 C15 117.2(5) . . ? C8 C14 C13 113.8(6) . . ? C15 C14 C13 103.5(5) . . ? C8 C14 H14 107.3 . . ? C15 C14 H14 107.3 . . ? C13 C14 H14 107.3 . . ? C14 C15 C16 103.6(5) . . ? C14 C15 H15A 111 . . ? C16 C15 H15A 111 . . ? C14 C15 H15B 111 . . ? C16 C15 H15B 111 . . ? H15A C15 H15B 109 . . ? C15 C16 C17 107.1(5) . . ? C15 C16 H16A 110.3 . . ? C17 C16 H16A 110.3 . . ? C15 C16 H16B 110.3 . . ? C17 C16 H16B 110.3 . . ? H16A C16 H16B 108.5 . . ? C20 C17 C16 113.4(6) . . ? C20 C17 C13 119.0(6) . . ? C16 C17 C13 102.4(6) . . ? C20 C17 H17 107.1 . . ? C16 C17 H17 107.1 . . ? C13 C17 H17 107.1 . . ? C13 C18 H18A 109.5 . . ? C13 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C13 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C10 C19 H19A 109.5 . . ? C10 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C10 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C17 C20 C21 112.6(6) . . ? C17 C20 C22 113.8(7) . . ? C21 C20 C22 110.4(7) . . ? C17 C20 H20 106.5 . . ? C21 C20 H20 106.5 . . ? C22 C20 H20 106.5 . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C23 C22 C20 116.2(6) . . ? C23 C22 H22A 108.2 . . ? C20 C22 H22A 108.2 . . ? C23 C22 H22B 108.2 . . ? C20 C22 H22B 108.2 . . ? H22A C22 H22B 107.4 . . ? C24 C23 C22 114.5(6) . . ? C24 C23 H23A 108.6 . . ? C22 C23 H23A 108.6 . . ? C24 C23 H23B 108.6 . . ? C22 C23 H23B 108.6 . . ? H23A C23 H23B 107.6 . . ? O5 C24 O4 123.7(7) . . ? O5 C24 C23 118.8(7) . . ? O4 C24 C23 117.5(7) . . ? C26 C25 H25A 109.5 . . ? C26 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C26 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C25 C26 C28 113(2) . . ? C25 C26 H26A 109.1 . . ? C28 C26 H26A 109.1 . . ? C25 C26 H26B 109.1 . . ? C28 C26 H26B 109.1 . . ? H26A C26 H26B 107.8 . . ? C29 C28 C26 114.6(15) . . ? C29 C28 H28A 108.6 . . ? C26 C28 H28A 108.6 . . ? C29 C28 H28B 108.6 . . ? C26 C28 H28B 108.6 . . ? H28A C28 H28B 107.6 . . ? C28 C29 C31 119.5(13) . . ? C28 C29 H29A 107.4 . . ? C31 C29 H29A 107.4 . . ? C28 C29 H29B 107.4 . . ? C31 C29 H29B 107.4 . . ? H29A C29 H29B 107 . . ? C29 C31 C32 115.5(11) . . ? C29 C31 H31A 108.4 . . ? C32 C31 H31A 108.4 . . ? C29 C31 H31B 108.4 . . ? C32 C31 H31B 108.4 . . ? H31A C31 H31B 107.5 . . ? C33 C32 C31 116.0(9) . . ? C33 C32 H32A 108.3 . . ? C31 C32 H32A 108.3 . . ? C33 C32 H32B 108.3 . . ? C31 C32 H32B 108.3 . . ? H32A C32 H32B 107.4 . . ? C34 C33 C32 114.2(9) . . ? C34 C33 H33A 108.7 . . ? C32 C33 H33A 108.7 . . ? C34 C33 H33B 108.7 . . ? C32 C33 H33B 108.7 . . ? H33A C33 H33B 107.6 . . ? C33 C34 C35 116.2(9) . . ? C33 C34 H34A 108.2 . . ? C35 C34 H34A 108.2 . . ? C33 C34 H34B 108.2 . . ? C35 C34 H34B 108.2 . . ? H34A C34 H34B 107.4 . . ? C36 C35 C34 117.7(9) . . ? C36 C35 H35A 107.9 . . ? C34 C35 H35A 107.9 . . ? C36 C35 H35B 107.9 . . ? C34 C35 H35B 107.9 . . ? H35A C35 H35B 107.2 . . ? C35 C36 C37 116.1(9) . . ? C35 C36 H36A 108.3 . . ? C37 C36 H36A 108.3 . . ? C35 C36 H36B 108.3 . . ? C37 C36 H36B 108.3 . . ? H36A C36 H36B 107.4 . . ? C36 C37 C38 117.0(9) . . ? C36 C37 H37A 108.1 . . ? C38 C37 H37A 108.1 . . ? C36 C37 H37B 108.1 . . ? C38 C37 H37B 108.1 . . ? H37A C37 H37B 107.3 . . ? C37 C38 C39 115.9(9) . . ? C37 C38 H38A 108.3 . . ? C39 C38 H38A 108.3 . . ? C37 C38 H38B 108.3 . . ? C39 C38 H38B 108.3 . . ? H38A C38 H38B 107.4 . . ? C40 C39 C38 113.6(9) . . ? C40 C39 H39A 108.9 . . ? C38 C39 H39A 108.9 . . ? C40 C39 H39B 108.9 . . ? C38 C39 H39B 108.9 . . ? H39A C39 H39B 107.7 . . ? C41 C40 C39 113.4(7) . . ? C41 C40 H40A 108.9 . . ? C39 C40 H40A 108.9 . . ? C41 C40 H40B 108.9 . . ? C39 C40 H40B 108.9 . . ? H40A C40 H40B 107.7 . . ? C42 C41 C40 112.3(7) . . ? C42 C41 H41A 109.1 . . ? C40 C41 H41A 109.1 . . ? C42 C41 H41B 109.1 . . ? C40 C41 H41B 109.1 . . ? H41A C41 H41B 107.9 . . ? C41 C42 N1 111.3(6) . . ? C41 C42 H42A 109.4 . . ? N1 C42 H42A 109.4 . . ? C41 C42 H42B 109.4 . . ? N1 C42 H42B 109.4 . . ? H42A C42 H42B 108 . . ? C42 N1 H1N 106(3) . . ? C42 N1 H2N 111(4) . . ? H1N N1 H2N 108(6) . . ? C42 N1 H3N 114(6) . . ? H1N N1 H3N 110(8) . . ? H2N N1 H3N 107(7) . . ? C3 O1 H1 109.5 . . ? C7 O2 H2 109.5 . . ? H1W O1W H2W 85(10) . . ? C12 O3 H3A 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C13 C17 C20 C21 -63.8(9) . . . . ? C13 C17 C20 C22 169.5(6) . . . . ? C17 C20 C22 C23 62.4(10) . . . . ? C20 C22 C23 C24 143.3(8) . . . . ? C13 C17 C20 C22 169.5(6) . . . . ? C17 C20 C22 C23 62.4(10) . . . . ? C20 C22 C23 C24 143.3(8) . . . . ? C16 C17 C20 C21 175.7(7) . . . . ? C17 C20 C21 C22 -128.5(9) . . . . ? C20 C21 C22 C23 124.4(9) . . . . ? C21 C22 C23 C24 111.7(8) . . . . ? C13 C17 C20 C21 -63.8(9) . . . . ? C17 C20 C21 C22 -128.5(9) . . . . ? C20 C21 C22 C23 124.4(9) . . . . ? C21 C22 C23 C24 111.7(8) . . . . ?