# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Takashi Ooi' _publ_contact_author_email TOOI@APCHEM.NAGOYA-U.AC.JP _publ_section_title ; Flexible Synthesis, Structural Determination, and Synthetic Application of a New C1-Symmetric Chiral Ammonium Betaine ; loop_ _publ_author_name 'Takashi Ooi' 'Kyohei Koshimoto' 'Daisuke Uraguchi' # Attachment '13.cif' data_9218kos _database_code_depnum_ccdc_archive 'CCDC 744058' #TrackingRef '13.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H22 N2 O4 S' _chemical_formula_weight 398.47 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 11.7097(16) _cell_length_b 16.840(2) _cell_length_c 21.042(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4149.2(10) _cell_formula_units_Z 8 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 3570 _cell_measurement_theta_min 2.28 _cell_measurement_theta_max 21.40 _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.276 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1680 _exptl_absorpt_coefficient_mu 0.184 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9468 _exptl_absorpt_correction_T_max 0.9641 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.366 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 31771 _diffrn_reflns_av_R_equivalents 0.0696 _diffrn_reflns_av_sigmaI/netI 0.0786 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.55 _diffrn_reflns_theta_max 28.33 _reflns_number_total 10322 _reflns_number_gt 8222 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.0504P)^2^+0.0793P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.01(7) _refine_ls_number_reflns 10322 _refine_ls_number_parameters 527 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0824 _refine_ls_R_factor_gt 0.0627 _refine_ls_wR_factor_ref 0.1277 _refine_ls_wR_factor_gt 0.1196 _refine_ls_goodness_of_fit_ref 1.084 _refine_ls_restrained_S_all 1.084 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.9246(2) 0.24361(18) 0.66382(14) 0.0310(6) Uani 1 1 d . . . C2 C 0.9229(2) 0.12289(18) 0.73890(13) 0.0275(6) Uani 1 1 d . . . C3 C 0.8323(2) 0.18598(16) 0.75616(12) 0.0231(6) Uani 1 1 d . . . C4 C 0.7119(2) 0.14717(15) 0.74918(13) 0.0232(6) Uani 1 1 d . . . H4 H 0.7065 0.1030 0.7808 0.028 Uiso 1 1 calc R . . C5 C 0.8609(2) 0.21474(16) 0.82353(13) 0.0254(6) Uani 1 1 d . . . C6 C 0.9521(2) 0.26684(18) 0.83112(14) 0.0315(6) Uani 1 1 d . . . H6 H 0.9904 0.2867 0.7946 0.038 Uiso 1 1 calc R . . C7 C 0.9877(2) 0.29019(19) 0.89075(15) 0.0339(7) Uani 1 1 d . . . H7 H 1.0506 0.3254 0.8951 0.041 Uiso 1 1 calc R . . C8 C 0.9319(2) 0.26219(19) 0.94427(14) 0.0338(7) Uani 1 1 d . . . H8 H 0.9567 0.2778 0.9854 0.041 Uiso 1 1 calc R . . C9 C 0.8401(3) 0.21150(19) 0.93766(14) 0.0343(7) Uani 1 1 d . . . H9 H 0.8005 0.1932 0.9743 0.041 Uiso 1 1 calc R . . C10 C 0.8053(2) 0.18715(18) 0.87756(14) 0.0300(6) Uani 1 1 d . . . H10 H 0.7431 0.1513 0.8734 0.036 Uiso 1 1 calc R . . C11 C 0.6933(2) 0.11182(17) 0.68308(14) 0.0276(6) Uani 1 1 d . . . C12 C 0.6591(3) 0.1587(2) 0.63215(14) 0.0369(7) Uani 1 1 d . . . H12 H 0.6471 0.2139 0.6382 0.044 Uiso 1 1 calc R . . C13 C 0.6422(3) 0.1254(2) 0.57255(15) 0.0457(9) Uani 1 1 d . . . H13 H 0.6193 0.1581 0.5380 0.055 Uiso 1 1 calc R . . C14 C 0.6584(3) 0.0456(2) 0.56324(16) 0.0472(9) Uani 1 1 d . . . H14 H 0.6470 0.0232 0.5223 0.057 Uiso 1 1 calc R . . C15 C 0.6912(3) -0.0019(2) 0.61317(16) 0.0429(8) Uani 1 1 d . . . H15 H 0.7021 -0.0572 0.6067 0.052 Uiso 1 1 calc R . . C16 C 0.7086(2) 0.03096(18) 0.67343(15) 0.0342(7) Uani 1 1 d . . . H16 H 0.7308 -0.0021 0.7078 0.041 Uiso 1 1 calc R . . C17 C 0.5274(2) 0.18601(16) 0.79418(12) 0.0207(5) Uani 1 1 d . . . C18 C 0.3357(2) 0.24323(17) 0.81398(13) 0.0259(6) Uani 1 1 d . . . C19 C 0.2698(2) 0.16864(19) 0.79930(15) 0.0357(7) Uani 1 1 d . . . H19A H 0.2687 0.1600 0.7533 0.054 Uiso 1 1 calc R . . H19B H 0.1913 0.1741 0.8149 0.054 Uiso 1 1 calc R . . H19C H 0.3064 0.1233 0.8202 0.054 Uiso 1 1 calc R . . C20 C 0.2826(3) 0.31537(19) 0.78231(15) 0.0384(8) Uani 1 1 d . . . H20A H 0.3320 0.3616 0.7888 0.058 Uiso 1 1 calc R . . H20B H 0.2074 0.3257 0.8010 0.058 Uiso 1 1 calc R . . H20C H 0.2740 0.3053 0.7367 0.058 Uiso 1 1 calc R . . C21 C 0.3521(3) 0.25641(19) 0.88493(14) 0.0323(7) Uani 1 1 d . . . H21A H 0.3908 0.2103 0.9035 0.048 Uiso 1 1 calc R . . H21B H 0.2775 0.2634 0.9052 0.048 Uiso 1 1 calc R . . H21C H 0.3986 0.3040 0.8918 0.048 Uiso 1 1 calc R . . C22 C 1.0678(2) 0.45006(17) 0.00516(13) 0.0252(6) Uani 1 1 d . . . C23 C 0.9368(2) 0.57187(17) -0.00505(13) 0.0261(6) Uani 1 1 d . . . C24 C 0.9181(2) 0.52544(15) 0.05748(12) 0.0199(5) Uani 1 1 d . . . C25 C 0.9517(2) 0.58056(16) 0.11410(12) 0.0214(5) Uani 1 1 d . . . H25 H 0.8981 0.6268 0.1137 0.026 Uiso 1 1 calc R . . C26 C 0.7928(2) 0.49832(16) 0.06004(13) 0.0258(6) Uani 1 1 d . . . C27 C 0.7622(2) 0.42481(17) 0.03681(13) 0.0286(6) Uani 1 1 d . . . H27 H 0.8190 0.3913 0.0189 0.034 Uiso 1 1 calc R . . C28 C 0.6503(3) 0.3990(2) 0.03908(15) 0.0371(8) Uani 1 1 d . . . H28 H 0.6307 0.3480 0.0233 0.045 Uiso 1 1 calc R . . C29 C 0.5670(3) 0.4475(2) 0.06430(18) 0.0525(10) Uani 1 1 d . . . H29 H 0.4902 0.4296 0.0668 0.063 Uiso 1 1 calc R . . C30 C 0.5954(3) 0.5209(3) 0.0855(2) 0.0708(14) Uani 1 1 d . . . H30 H 0.5377 0.5547 0.1022 0.085 Uiso 1 1 calc R . . C31 C 0.7085(3) 0.5476(2) 0.08327(19) 0.0503(10) Uani 1 1 d . . . H31 H 0.7271 0.5994 0.0977 0.060 Uiso 1 1 calc R . . C32 C 1.0720(2) 0.61314(18) 0.10770(13) 0.0293(6) Uani 1 1 d . . . C33 C 1.0884(3) 0.6877(2) 0.08144(16) 0.0430(8) Uani 1 1 d . . . H33 H 1.0244 0.7181 0.0681 0.052 Uiso 1 1 calc R . . C34 C 1.1982(4) 0.7184(3) 0.0745(2) 0.0663(13) Uani 1 1 d . . . H34 H 1.2091 0.7695 0.0564 0.080 Uiso 1 1 calc R . . C35 C 1.2911(3) 0.6742(3) 0.0938(2) 0.0739(16) Uani 1 1 d . . . H35 H 1.3660 0.6949 0.0891 0.089 Uiso 1 1 calc R . . C36 C 1.2753(3) 0.6004(3) 0.11994(19) 0.0615(12) Uani 1 1 d . . . H36 H 1.3394 0.5699 0.1330 0.074 Uiso 1 1 calc R . . C37 C 1.1665(2) 0.5701(2) 0.12738(15) 0.0402(8) Uani 1 1 d . . . H37 H 1.1564 0.5193 0.1462 0.048 Uiso 1 1 calc R . . C38 C 0.8748(2) 0.56834(16) 0.22184(12) 0.0213(5) Uani 1 1 d . . . C39 C 0.8088(3) 0.53232(18) 0.32946(14) 0.0341(7) Uani 1 1 d . . . C40 C 0.8356(3) 0.4589(2) 0.36867(15) 0.0455(8) Uani 1 1 d . . . H40A H 0.8121 0.4114 0.3452 0.068 Uiso 1 1 calc R . . H40B H 0.7942 0.4614 0.4091 0.068 Uiso 1 1 calc R . . H40C H 0.9179 0.4566 0.3770 0.068 Uiso 1 1 calc R . . C41 C 0.8508(4) 0.6062(2) 0.36225(17) 0.0617(12) Uani 1 1 d . . . H41A H 0.9338 0.6032 0.3675 0.093 Uiso 1 1 calc R . . H41B H 0.8144 0.6107 0.4040 0.093 Uiso 1 1 calc R . . H41C H 0.8314 0.6528 0.3365 0.093 Uiso 1 1 calc R . . C42 C 0.6829(3) 0.5354(2) 0.3120(2) 0.0593(11) Uani 1 1 d . . . H42A H 0.6686 0.5818 0.2851 0.089 Uiso 1 1 calc R . . H42B H 0.6370 0.5394 0.3508 0.089 Uiso 1 1 calc R . . H42C H 0.6621 0.4870 0.2889 0.089 Uiso 1 1 calc R . . H43 H 0.806(2) 0.2887(16) 0.7105(12) 0.012(7) Uiso 1 1 d . . . H44 H 0.626(2) 0.2471(17) 0.7470(12) 0.012(7) Uiso 1 1 d . . . H45 H 1.003(2) 0.4267(16) 0.0835(12) 0.010(6) Uiso 1 1 d . . . H46 H 0.961(2) 0.4922(17) 0.1790(13) 0.019(7) Uiso 1 1 d . . . N1 N 0.84655(19) 0.24881(15) 0.71034(11) 0.0250(5) Uani 1 1 d . . . N2 N 0.62514(19) 0.20524(14) 0.76492(11) 0.0235(5) Uani 1 1 d . . . N3 N 0.99526(19) 0.45794(13) 0.05401(11) 0.0229(5) Uani 1 1 d . . . N4 N 0.93360(19) 0.53813(14) 0.17323(10) 0.0240(5) Uani 1 1 d . . . O1 O 0.9405(2) 0.29009(15) 0.62119(11) 0.0513(6) Uani 1 1 d . . . O2 O 0.93205(18) 0.06097(12) 0.76590(10) 0.0382(5) Uani 1 1 d . . . O3 O 0.51387(15) 0.12587(11) 0.82613(9) 0.0260(4) Uani 1 1 d . . . O4 O 0.45022(15) 0.24253(11) 0.78382(9) 0.0273(4) Uani 1 1 d . . . O5 O 1.13814(17) 0.39857(13) -0.00203(10) 0.0365(5) Uani 1 1 d . . . O6 O 0.88623(18) 0.63090(13) -0.01857(10) 0.0367(5) Uani 1 1 d . . . O7 O 0.82796(15) 0.63398(11) 0.22091(9) 0.0254(4) Uani 1 1 d . . . O8 O 0.87528(17) 0.51808(12) 0.27074(9) 0.0302(5) Uani 1 1 d . . . S1 S 1.00894(6) 0.15495(5) 0.67436(4) 0.03336(18) Uani 1 1 d . . . S2 S 1.04438(6) 0.52740(5) -0.05232(3) 0.03298(18) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0233(14) 0.0363(17) 0.0335(16) 0.0025(13) 0.0028(12) -0.0008(13) C2 0.0226(14) 0.0320(16) 0.0278(14) -0.0040(12) -0.0024(11) 0.0034(13) C3 0.0190(12) 0.0228(14) 0.0277(14) 0.0013(11) 0.0033(10) 0.0026(11) C4 0.0221(13) 0.0174(13) 0.0300(14) 0.0028(11) 0.0022(11) 0.0005(12) C5 0.0201(12) 0.0264(14) 0.0297(14) -0.0014(12) -0.0021(11) 0.0050(11) C6 0.0248(13) 0.0368(17) 0.0329(15) -0.0047(13) 0.0029(12) -0.0012(13) C7 0.0232(14) 0.0376(17) 0.0410(17) -0.0097(14) 0.0015(13) 0.0000(13) C8 0.0317(15) 0.0395(17) 0.0303(15) -0.0111(13) -0.0068(13) 0.0062(14) C9 0.0358(16) 0.0422(18) 0.0251(15) 0.0010(13) 0.0045(12) 0.0028(15) C10 0.0252(13) 0.0320(16) 0.0329(15) -0.0002(13) 0.0006(12) 0.0017(13) C11 0.0219(13) 0.0312(16) 0.0298(15) -0.0004(12) 0.0038(11) -0.0032(12) C12 0.0347(16) 0.0405(18) 0.0356(17) 0.0003(14) -0.0020(13) -0.0003(15) C13 0.0455(19) 0.062(2) 0.0299(17) 0.0022(16) -0.0058(14) 0.0046(18) C14 0.0364(17) 0.074(3) 0.0316(18) -0.0170(18) 0.0035(14) -0.0104(18) C15 0.0474(19) 0.0391(19) 0.0423(19) -0.0127(15) 0.0089(15) -0.0149(16) C16 0.0343(15) 0.0302(16) 0.0380(16) -0.0018(14) 0.0059(13) -0.0043(14) C17 0.0207(13) 0.0223(13) 0.0191(12) -0.0012(10) -0.0021(10) -0.0016(11) C18 0.0199(12) 0.0278(15) 0.0302(15) -0.0001(12) 0.0059(11) 0.0060(12) C19 0.0227(14) 0.0406(18) 0.0438(18) -0.0038(15) 0.0009(13) -0.0015(13) C20 0.0318(16) 0.0412(19) 0.0422(18) 0.0078(15) 0.0075(14) 0.0141(15) C21 0.0363(16) 0.0308(16) 0.0298(15) -0.0016(13) 0.0033(12) -0.0007(14) C22 0.0219(13) 0.0288(15) 0.0249(14) 0.0006(11) -0.0052(11) 0.0009(12) C23 0.0204(13) 0.0308(16) 0.0271(14) 0.0017(12) -0.0012(11) 0.0017(12) C24 0.0184(11) 0.0201(13) 0.0212(12) 0.0001(11) -0.0004(10) 0.0025(11) C25 0.0187(12) 0.0215(13) 0.0239(13) -0.0023(11) 0.0029(11) 0.0008(11) C26 0.0229(13) 0.0276(14) 0.0270(14) 0.0011(12) -0.0026(11) -0.0038(12) C27 0.0282(14) 0.0308(15) 0.0266(15) 0.0032(12) -0.0044(11) -0.0015(13) C28 0.0356(17) 0.0385(18) 0.0372(18) 0.0021(14) -0.0087(14) -0.0098(15) C29 0.0286(17) 0.068(3) 0.061(2) -0.008(2) 0.0016(16) -0.0217(18) C30 0.0177(15) 0.081(3) 0.114(4) -0.043(3) 0.0110(18) -0.0047(19) C31 0.0208(15) 0.050(2) 0.081(3) -0.0285(19) -0.0004(16) -0.0031(15) C32 0.0258(14) 0.0346(17) 0.0275(14) -0.0113(12) 0.0039(12) -0.0072(13) C33 0.0387(18) 0.042(2) 0.048(2) -0.0100(16) 0.0118(15) -0.0139(16) C34 0.064(3) 0.068(3) 0.066(3) -0.025(2) 0.026(2) -0.042(2) C35 0.037(2) 0.123(4) 0.061(3) -0.051(3) 0.0180(19) -0.042(3) C36 0.0248(17) 0.110(4) 0.050(2) -0.034(2) -0.0023(16) -0.008(2) C37 0.0220(14) 0.065(2) 0.0341(17) -0.0170(16) -0.0027(12) 0.0008(15) C38 0.0181(12) 0.0233(14) 0.0224(13) -0.0040(11) -0.0023(10) -0.0024(11) C39 0.0421(16) 0.0305(16) 0.0297(15) 0.0021(13) 0.0138(13) -0.0039(14) C40 0.062(2) 0.043(2) 0.0321(17) 0.0063(15) 0.0093(16) -0.0031(18) C41 0.110(4) 0.043(2) 0.0316(19) -0.0037(16) 0.009(2) -0.021(2) C42 0.0420(19) 0.053(2) 0.083(3) 0.020(2) 0.0258(19) 0.0026(19) N1 0.0226(11) 0.0214(12) 0.0311(13) 0.0055(10) 0.0030(10) 0.0054(10) N2 0.0238(11) 0.0169(12) 0.0298(12) 0.0081(10) 0.0024(10) -0.0005(10) N3 0.0252(11) 0.0226(12) 0.0210(11) 0.0038(10) 0.0004(10) 0.0037(10) N4 0.0245(11) 0.0223(12) 0.0253(11) 0.0030(10) 0.0010(9) 0.0086(10) O1 0.0416(13) 0.0611(16) 0.0513(14) 0.0241(13) 0.0180(11) 0.0058(12) O2 0.0390(12) 0.0305(11) 0.0452(13) 0.0038(10) 0.0003(10) 0.0109(10) O3 0.0262(9) 0.0225(9) 0.0294(10) 0.0055(8) 0.0012(8) -0.0015(8) O4 0.0219(9) 0.0285(10) 0.0313(10) 0.0088(8) 0.0054(8) 0.0051(9) O5 0.0300(11) 0.0391(13) 0.0405(13) -0.0019(10) 0.0047(9) 0.0108(10) O6 0.0336(11) 0.0375(13) 0.0390(12) 0.0119(10) 0.0003(9) 0.0087(10) O7 0.0257(9) 0.0204(10) 0.0301(10) -0.0040(8) 0.0010(8) 0.0037(8) O8 0.0367(10) 0.0289(11) 0.0250(10) 0.0038(8) 0.0058(8) 0.0086(9) S1 0.0256(3) 0.0403(4) 0.0341(4) -0.0029(3) 0.0067(3) 0.0074(3) S2 0.0314(4) 0.0433(4) 0.0242(3) 0.0068(3) 0.0058(3) 0.0070(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.205(3) . ? C1 N1 1.342(3) . ? C1 S1 1.804(3) . ? C2 O2 1.192(3) . ? C2 C3 1.545(4) . ? C2 S1 1.775(3) . ? C3 N1 1.441(3) . ? C3 C5 1.535(4) . ? C3 C4 1.561(4) . ? C4 N2 1.449(3) . ? C4 C11 1.528(4) . ? C4 H4 1.0000 . ? C5 C10 1.390(4) . ? C5 C6 1.391(4) . ? C6 C7 1.380(4) . ? C6 H6 0.9500 . ? C7 C8 1.385(4) . ? C7 H7 0.9500 . ? C8 C9 1.380(4) . ? C8 H8 0.9500 . ? C9 C10 1.390(4) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? C11 C16 1.388(4) . ? C11 C12 1.390(4) . ? C12 C13 1.388(5) . ? C12 H12 0.9500 . ? C13 C14 1.371(5) . ? C13 H13 0.9500 . ? C14 C15 1.376(5) . ? C14 H14 0.9500 . ? C15 C16 1.398(4) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 O3 1.226(3) . ? C17 O4 1.331(3) . ? C17 N2 1.339(3) . ? C18 O4 1.483(3) . ? C18 C19 1.506(4) . ? C18 C20 1.519(4) . ? C18 C21 1.521(4) . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 O5 1.206(3) . ? C22 N3 1.340(3) . ? C22 S2 1.798(3) . ? C23 O6 1.191(3) . ? C23 C24 1.546(4) . ? C23 S2 1.771(3) . ? C24 N3 1.454(3) . ? C24 C26 1.538(3) . ? C24 C25 1.561(4) . ? C25 N4 1.450(3) . ? C25 C32 1.518(4) . ? C25 H25 1.0000 . ? C26 C27 1.378(4) . ? C26 C31 1.379(4) . ? C27 C28 1.381(4) . ? C27 H27 0.9500 . ? C28 C29 1.378(5) . ? C28 H28 0.9500 . ? C29 C30 1.356(6) . ? C29 H29 0.9500 . ? C30 C31 1.399(4) . ? C30 H30 0.9500 . ? C31 H31 0.9500 . ? C32 C33 1.385(5) . ? C32 C37 1.386(4) . ? C33 C34 1.393(5) . ? C33 H33 0.9500 . ? C34 C35 1.379(7) . ? C34 H34 0.9500 . ? C35 C36 1.372(7) . ? C35 H35 0.9500 . ? C36 C37 1.380(5) . ? C36 H36 0.9500 . ? C37 H37 0.9500 . ? C38 O7 1.234(3) . ? C38 O8 1.332(3) . ? C38 N4 1.334(3) . ? C39 O8 1.480(3) . ? C39 C41 1.506(5) . ? C39 C40 1.519(4) . ? C39 C42 1.520(5) . ? C40 H40A 0.9800 . ? C40 H40B 0.9800 . ? C40 H40C 0.9800 . ? C41 H41A 0.9800 . ? C41 H41B 0.9800 . ? C41 H41C 0.9800 . ? C42 H42A 0.9800 . ? C42 H42B 0.9800 . ? C42 H42C 0.9800 . ? N1 H43 0.83(3) . ? N2 H44 0.80(3) . ? N3 H45 0.82(3) . ? N4 H46 0.85(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 N1 127.3(3) . . ? O1 C1 S1 123.0(2) . . ? N1 C1 S1 109.7(2) . . ? O2 C2 C3 123.4(3) . . ? O2 C2 S1 125.4(2) . . ? C3 C2 S1 111.1(2) . . ? N1 C3 C5 111.2(2) . . ? N1 C3 C2 105.5(2) . . ? C5 C3 C2 106.5(2) . . ? N1 C3 C4 110.4(2) . . ? C5 C3 C4 114.6(2) . . ? C2 C3 C4 108.1(2) . . ? N2 C4 C11 111.8(2) . . ? N2 C4 C3 109.2(2) . . ? C11 C4 C3 112.2(2) . . ? N2 C4 H4 107.8 . . ? C11 C4 H4 107.8 . . ? C3 C4 H4 107.8 . . ? C10 C5 C6 118.4(3) . . ? C10 C5 C3 123.2(2) . . ? C6 C5 C3 118.2(2) . . ? C7 C6 C5 121.1(3) . . ? C7 C6 H6 119.5 . . ? C5 C6 H6 119.5 . . ? C6 C7 C8 120.0(3) . . ? C6 C7 H7 120.0 . . ? C8 C7 H7 120.0 . . ? C9 C8 C7 119.8(3) . . ? C9 C8 H8 120.1 . . ? C7 C8 H8 120.1 . . ? C8 C9 C10 120.1(3) . . ? C8 C9 H9 119.9 . . ? C10 C9 H9 119.9 . . ? C5 C10 C9 120.6(3) . . ? C5 C10 H10 119.7 . . ? C9 C10 H10 119.7 . . ? C16 C11 C12 118.8(3) . . ? C16 C11 C4 119.8(3) . . ? C12 C11 C4 121.4(3) . . ? C13 C12 C11 120.6(3) . . ? C13 C12 H12 119.7 . . ? C11 C12 H12 119.7 . . ? C14 C13 C12 120.3(3) . . ? C14 C13 H13 119.8 . . ? C12 C13 H13 119.8 . . ? C13 C14 C15 120.0(3) . . ? C13 C14 H14 120.0 . . ? C15 C14 H14 120.0 . . ? C14 C15 C16 120.2(3) . . ? C14 C15 H15 119.9 . . ? C16 C15 H15 119.9 . . ? C11 C16 C15 120.2(3) . . ? C11 C16 H16 119.9 . . ? C15 C16 H16 119.9 . . ? O3 C17 O4 126.4(2) . . ? O3 C17 N2 124.2(2) . . ? O4 C17 N2 109.4(2) . . ? O4 C18 C19 111.6(2) . . ? O4 C18 C20 100.9(2) . . ? C19 C18 C20 111.5(2) . . ? O4 C18 C21 107.9(2) . . ? C19 C18 C21 112.8(2) . . ? C20 C18 C21 111.4(2) . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C18 C20 H20A 109.5 . . ? C18 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C18 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C18 C21 H21A 109.5 . . ? C18 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C18 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? O5 C22 N3 126.9(3) . . ? O5 C22 S2 122.7(2) . . ? N3 C22 S2 110.4(2) . . ? O6 C23 C24 123.7(2) . . ? O6 C23 S2 124.9(2) . . ? C24 C23 S2 111.39(19) . . ? N3 C24 C26 111.3(2) . . ? N3 C24 C23 105.4(2) . . ? C26 C24 C23 108.4(2) . . ? N3 C24 C25 110.3(2) . . ? C26 C24 C25 113.0(2) . . ? C23 C24 C25 108.3(2) . . ? N4 C25 C32 112.9(2) . . ? N4 C25 C24 109.0(2) . . ? C32 C25 C24 112.4(2) . . ? N4 C25 H25 107.4 . . ? C32 C25 H25 107.4 . . ? C24 C25 H25 107.4 . . ? C27 C26 C31 118.7(3) . . ? C27 C26 C24 120.1(2) . . ? C31 C26 C24 121.1(3) . . ? C26 C27 C28 121.1(3) . . ? C26 C27 H27 119.4 . . ? C28 C27 H27 119.4 . . ? C29 C28 C27 119.9(3) . . ? C29 C28 H28 120.1 . . ? C27 C28 H28 120.1 . . ? C30 C29 C28 119.6(3) . . ? C30 C29 H29 120.2 . . ? C28 C29 H29 120.2 . . ? C29 C30 C31 120.9(3) . . ? C29 C30 H30 119.6 . . ? C31 C30 H30 119.6 . . ? C26 C31 C30 119.8(3) . . ? C26 C31 H31 120.1 . . ? C30 C31 H31 120.1 . . ? C33 C32 C37 118.8(3) . . ? C33 C32 C25 119.4(3) . . ? C37 C32 C25 121.7(3) . . ? C32 C33 C34 120.4(4) . . ? C32 C33 H33 119.8 . . ? C34 C33 H33 119.8 . . ? C35 C34 C33 119.7(4) . . ? C35 C34 H34 120.1 . . ? C33 C34 H34 120.1 . . ? C36 C35 C34 120.1(4) . . ? C36 C35 H35 120.0 . . ? C34 C35 H35 120.0 . . ? C35 C36 C37 120.3(4) . . ? C35 C36 H36 119.9 . . ? C37 C36 H36 119.9 . . ? C36 C37 C32 120.7(4) . . ? C36 C37 H37 119.7 . . ? C32 C37 H37 119.7 . . ? O7 C38 O8 125.7(2) . . ? O7 C38 N4 124.0(2) . . ? O8 C38 N4 110.4(2) . . ? O8 C39 C41 110.2(3) . . ? O8 C39 C40 102.3(2) . . ? C41 C39 C40 110.9(3) . . ? O8 C39 C42 108.3(3) . . ? C41 C39 C42 113.5(3) . . ? C40 C39 C42 111.1(3) . . ? C39 C40 H40A 109.5 . . ? C39 C40 H40B 109.5 . . ? H40A C40 H40B 109.5 . . ? C39 C40 H40C 109.5 . . ? H40A C40 H40C 109.5 . . ? H40B C40 H40C 109.5 . . ? C39 C41 H41A 109.5 . . ? C39 C41 H41B 109.5 . . ? H41A C41 H41B 109.5 . . ? C39 C41 H41C 109.5 . . ? H41A C41 H41C 109.5 . . ? H41B C41 H41C 109.5 . . ? C39 C42 H42A 109.5 . . ? C39 C42 H42B 109.5 . . ? H42A C42 H42B 109.5 . . ? C39 C42 H42C 109.5 . . ? H42A C42 H42C 109.5 . . ? H42B C42 H42C 109.5 . . ? C1 N1 C3 121.3(2) . . ? C1 N1 H43 116.8(18) . . ? C3 N1 H43 121.9(18) . . ? C17 N2 C4 122.8(2) . . ? C17 N2 H44 116.1(19) . . ? C4 N2 H44 118.7(19) . . ? C22 N3 C24 120.6(2) . . ? C22 N3 H45 116.6(18) . . ? C24 N3 H45 122.3(18) . . ? C38 N4 C25 123.0(2) . . ? C38 N4 H46 115.7(19) . . ? C25 N4 H46 121.3(19) . . ? C17 O4 C18 123.3(2) . . ? C38 O8 C39 122.7(2) . . ? C2 S1 C1 92.01(13) . . ? C23 S2 C22 92.11(13) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 28.33 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.430 _refine_diff_density_min -0.224 _refine_diff_density_rms 0.057 # Attachment '1a.cif' data_8702kos _database_code_depnum_ccdc_archive 'CCDC 744059' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C38 H41 N O4' _chemical_formula_weight 575.72 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 11.552(5) _cell_length_b 9.827(5) _cell_length_c 14.569(7) _cell_angle_alpha 90.00 _cell_angle_beta 109.875(11) _cell_angle_gamma 90.00 _cell_volume 1555.4(13) _cell_formula_units_Z 2 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 3331 _cell_measurement_theta_min 2.55 _cell_measurement_theta_max 28.19 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.229 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 616 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9543 _exptl_absorpt_correction_T_max 0.9922 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.366 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11719 _diffrn_reflns_av_R_equivalents 0.0329 _diffrn_reflns_av_sigmaI/netI 0.0515 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.49 _diffrn_reflns_theta_max 28.39 _reflns_number_total 6478 _reflns_number_gt 5585 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.0622P)^2^+0.2247P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -1.4(12) _refine_ls_number_reflns 6478 _refine_ls_number_parameters 399 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0593 _refine_ls_R_factor_gt 0.0496 _refine_ls_wR_factor_ref 0.1216 _refine_ls_wR_factor_gt 0.1157 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.51765(12) 0.59231(15) 0.68916(10) 0.0245(3) Uani 1 1 d . . . C1 C 0.59908(18) 0.4179(2) 0.80795(14) 0.0203(4) Uani 1 1 d . . . C4 C 0.36256(18) 0.3735(2) 0.81171(15) 0.0229(4) Uani 1 1 d . . . H4 H 0.2815 0.3590 0.8124 0.028 Uiso 1 1 calc R . . C11 C 0.72748(18) 0.4371(2) 0.80769(13) 0.0202(4) Uani 1 1 d . . . C5 C 0.45937(18) 0.2964(2) 0.87544(14) 0.0226(4) Uani 1 1 d . . . C10 C 0.58008(18) 0.3182(2) 0.87328(13) 0.0208(4) Uani 1 1 d . . . C3 C 0.37983(18) 0.4688(2) 0.74865(14) 0.0215(4) Uani 1 1 d . . . C6 C 0.43784(19) 0.1971(2) 0.93814(15) 0.0275(5) Uani 1 1 d . . . H6 H 0.3563 0.1831 0.9378 0.033 Uiso 1 1 calc R . . C9 C 0.6754(2) 0.2390(2) 0.93849(15) 0.0282(5) Uani 1 1 d . . . H9 H 0.7577 0.2523 0.9407 0.034 Uiso 1 1 calc R . . C19 C 0.7402(2) 0.6596(2) 0.89424(15) 0.0271(4) Uani 1 1 d . . . H19 H 0.6570 0.6511 0.8910 0.033 Uiso 1 1 calc R . . C20 C 0.79415(18) 0.5554(2) 0.85430(14) 0.0215(4) Uani 1 1 d . . . C2 C 0.50225(18) 0.4975(2) 0.74767(14) 0.0208(4) Uani 1 1 d . . . C13 C 0.91510(18) 0.3479(2) 0.78677(14) 0.0224(4) Uani 1 1 d . . . C14 C 0.97671(18) 0.4644(2) 0.82786(15) 0.0241(4) Uani 1 1 d . . . H14 H 1.0608 0.4737 0.8339 0.029 Uiso 1 1 calc R . . C33 C 0.71626(19) 0.2155(2) 0.71737(14) 0.0239(4) Uani 1 1 d . . . H33A H 0.6488 0.1950 0.7427 0.029 Uiso 1 1 calc R . . H33B H 0.7728 0.1365 0.7326 0.029 Uiso 1 1 calc R . . N1 N 0.66096(15) 0.23027(19) 0.60581(12) 0.0254(4) Uani 1 1 d . . . C21 C 0.26876(18) 0.5346(2) 0.67933(14) 0.0226(4) Uani 1 1 d . . . C7 C 0.5311(2) 0.1212(2) 0.99890(17) 0.0337(5) Uani 1 1 d . . . H7 H 0.5154 0.0548 1.0406 0.040 Uiso 1 1 calc R . . C12 C 0.78548(17) 0.3379(2) 0.77094(13) 0.0209(4) Uani 1 1 d . . . C15 C 0.91925(18) 0.5705(2) 0.86140(14) 0.0234(4) Uani 1 1 d . . . C8 C 0.6518(2) 0.1434(3) 0.99857(17) 0.0331(5) Uani 1 1 d . . . H8 H 0.7178 0.0913 1.0407 0.040 Uiso 1 1 calc R . . C27 C 0.98964(18) 0.2336(2) 0.76820(15) 0.0242(4) Uani 1 1 d . . . C16 C 0.9845(2) 0.6885(2) 0.90616(16) 0.0299(5) Uani 1 1 d . . . H16 H 1.0680 0.6992 0.9106 0.036 Uiso 1 1 calc R . . C22 C 0.2097(2) 0.4747(2) 0.58904(15) 0.0290(5) Uani 1 1 d . . . H22 H 0.2476 0.4003 0.5685 0.035 Uiso 1 1 calc R . . C35 C 0.6227(2) 0.0912(3) 0.56383(18) 0.0350(5) Uani 1 1 d . . . H35A H 0.6956 0.0331 0.5776 0.052 Uiso 1 1 calc R . . H35B H 0.5816 0.0984 0.4931 0.052 Uiso 1 1 calc R . . H35C H 0.5660 0.0513 0.5934 0.052 Uiso 1 1 calc R . . C18 C 0.8064(2) 0.7719(3) 0.93729(17) 0.0333(5) Uani 1 1 d . . . H18 H 0.7687 0.8403 0.9636 0.040 Uiso 1 1 calc R . . C32 C 1.05664(19) 0.2513(2) 0.70537(16) 0.0288(5) Uani 1 1 d . . . H32 H 1.0475 0.3326 0.6683 0.035 Uiso 1 1 calc R . . C17 C 0.9296(2) 0.7873(3) 0.94306(17) 0.0337(5) Uani 1 1 d . . . H17 H 0.9745 0.8661 0.9725 0.040 Uiso 1 1 calc R . . C31 C 1.1368(2) 0.1504(3) 0.69693(18) 0.0379(6) Uani 1 1 d . . . H31 H 1.1822 0.1632 0.6542 0.045 Uiso 1 1 calc R . . C26 C 0.2124(2) 0.6440(3) 0.70675(19) 0.0411(6) Uani 1 1 d . . . H26 H 0.2522 0.6878 0.7675 0.049 Uiso 1 1 calc R . . C23 C 0.0966(2) 0.5219(3) 0.52857(16) 0.0355(5) Uani 1 1 d . . . H23 H 0.0575 0.4801 0.4669 0.043 Uiso 1 1 calc R . . C24 C 0.0403(2) 0.6294(3) 0.55761(19) 0.0392(6) Uani 1 1 d . . . H24 H -0.0379 0.6609 0.5166 0.047 Uiso 1 1 calc R . . C34 C 0.7516(2) 0.2865(3) 0.56262(16) 0.0349(5) Uani 1 1 d . . . H34A H 0.7745 0.3792 0.5868 0.052 Uiso 1 1 calc R . . H34B H 0.7144 0.2882 0.4913 0.052 Uiso 1 1 calc R . . H34C H 0.8253 0.2290 0.5815 0.052 Uiso 1 1 calc R . . C36 C 0.5503(2) 0.3204(3) 0.57727(16) 0.0340(5) Uani 1 1 d . . . H36A H 0.5153 0.3259 0.5060 0.051 Uiso 1 1 calc R . . H36B H 0.5741 0.4116 0.6043 0.051 Uiso 1 1 calc R . . H36C H 0.4888 0.2828 0.6029 0.051 Uiso 1 1 calc R . . C28 C 1.0037(2) 0.1127(3) 0.8211(2) 0.0375(6) Uani 1 1 d . . . H28 H 0.9577 0.0983 0.8633 0.045 Uiso 1 1 calc R . . C29 C 1.0845(3) 0.0137(3) 0.8122(3) 0.0535(8) Uani 1 1 d . . . H29 H 1.0947 -0.0678 0.8492 0.064 Uiso 1 1 calc R . . C30 C 1.1504(2) 0.0333(3) 0.7496(2) 0.0487(7) Uani 1 1 d . . . H30 H 1.2053 -0.0352 0.7434 0.058 Uiso 1 1 calc R . . C25 C 0.0984(3) 0.6906(3) 0.6464(2) 0.0505(7) Uani 1 1 d . . . H25 H 0.0602 0.7650 0.6665 0.061 Uiso 1 1 calc R . . O4 O 0.3243(2) 0.0915(2) 0.57671(16) 0.0583(6) Uani 1 1 d . . . O3 O 0.4516(2) 0.85733(19) 0.67865(13) 0.0497(5) Uani 1 1 d . . . H3 H 0.4658 0.7733 0.6818 0.075 Uiso 1 1 calc R . . O2 O 0.6868(2) 0.6466(3) 0.61157(16) 0.0674(7) Uani 1 1 d . . . H2 H 0.6410 0.6343 0.6449 0.101 Uiso 1 1 calc R . . C38 C 0.7667(3) 0.7513(3) 0.6509(2) 0.0501(7) Uani 1 1 d . . . H38A H 0.7892 0.7961 0.5993 0.075 Uiso 1 1 calc R . . H38B H 0.8409 0.7154 0.7005 0.075 Uiso 1 1 calc R . . H38C H 0.7270 0.8173 0.6810 0.075 Uiso 1 1 calc R . . C37 C 0.4916(3) 0.9127(3) 0.7733(2) 0.0525(7) Uani 1 1 d . . . H37A H 0.4580 0.8591 0.8151 0.079 Uiso 1 1 calc R . . H37B H 0.4631 1.0070 0.7706 0.079 Uiso 1 1 calc R . . H37C H 0.5817 0.9106 0.8001 0.079 Uiso 1 1 calc R . . H39 H 0.329(4) 0.100(5) 0.514(3) 0.090(13) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0235(7) 0.0270(8) 0.0251(7) 0.0035(6) 0.0112(6) 0.0002(6) C1 0.0195(9) 0.0229(10) 0.0210(9) -0.0021(7) 0.0101(7) -0.0006(8) C4 0.0174(9) 0.0277(10) 0.0251(9) -0.0022(8) 0.0091(7) -0.0028(8) C11 0.0199(9) 0.0247(10) 0.0170(8) 0.0031(7) 0.0074(7) 0.0002(8) C5 0.0234(10) 0.0242(10) 0.0222(9) -0.0028(8) 0.0104(8) -0.0020(8) C10 0.0214(9) 0.0240(10) 0.0184(8) -0.0022(7) 0.0085(7) -0.0001(8) C3 0.0213(9) 0.0213(10) 0.0217(9) -0.0046(7) 0.0073(7) 0.0013(8) C6 0.0252(10) 0.0322(12) 0.0285(10) 0.0022(9) 0.0135(8) -0.0033(9) C9 0.0238(10) 0.0363(12) 0.0259(10) 0.0017(9) 0.0103(8) 0.0027(9) C19 0.0265(10) 0.0320(12) 0.0248(10) -0.0019(9) 0.0111(8) 0.0007(9) C20 0.0233(9) 0.0239(10) 0.0171(8) 0.0004(7) 0.0067(7) 0.0007(8) C2 0.0228(9) 0.0227(10) 0.0181(9) -0.0018(7) 0.0087(7) -0.0010(8) C13 0.0208(9) 0.0263(11) 0.0221(9) 0.0028(8) 0.0097(8) 0.0011(8) C14 0.0173(9) 0.0300(11) 0.0253(9) 0.0034(8) 0.0078(8) 0.0010(8) C33 0.0229(9) 0.0257(10) 0.0252(10) -0.0006(8) 0.0109(8) -0.0002(8) N1 0.0218(8) 0.0280(9) 0.0257(9) -0.0061(7) 0.0074(7) 0.0008(7) C21 0.0192(9) 0.0266(10) 0.0240(9) 0.0032(8) 0.0097(8) -0.0016(8) C7 0.0392(12) 0.0339(12) 0.0338(11) 0.0096(10) 0.0197(10) 0.0004(10) C12 0.0198(9) 0.0245(10) 0.0192(9) 0.0007(8) 0.0077(7) 0.0001(8) C15 0.0222(10) 0.0262(11) 0.0212(9) 0.0030(8) 0.0066(8) -0.0006(8) C8 0.0314(11) 0.0381(13) 0.0292(11) 0.0120(9) 0.0094(9) 0.0074(10) C27 0.0175(9) 0.0273(11) 0.0278(10) -0.0031(8) 0.0079(8) -0.0015(8) C16 0.0247(10) 0.0321(12) 0.0315(11) -0.0018(9) 0.0077(9) -0.0046(9) C22 0.0296(11) 0.0335(12) 0.0251(10) 0.0002(9) 0.0109(9) 0.0048(9) C35 0.0357(12) 0.0316(12) 0.0366(12) -0.0126(10) 0.0109(10) -0.0024(11) C18 0.0402(13) 0.0310(12) 0.0310(11) -0.0080(9) 0.0149(10) 0.0022(10) C32 0.0204(10) 0.0383(13) 0.0292(10) -0.0025(9) 0.0106(8) -0.0028(9) C17 0.0373(12) 0.0291(12) 0.0314(11) -0.0070(9) 0.0076(10) -0.0083(10) C31 0.0235(11) 0.0530(17) 0.0403(13) -0.0154(12) 0.0148(10) -0.0020(11) C26 0.0380(13) 0.0408(15) 0.0370(13) -0.0088(11) 0.0032(10) 0.0103(11) C23 0.0330(12) 0.0454(14) 0.0230(10) 0.0029(10) 0.0029(9) -0.0022(11) C24 0.0256(11) 0.0522(16) 0.0364(12) 0.0085(11) 0.0061(10) 0.0091(11) C34 0.0351(12) 0.0465(14) 0.0249(10) 0.0006(10) 0.0125(9) -0.0021(11) C36 0.0304(11) 0.0389(13) 0.0284(11) -0.0037(10) 0.0046(9) 0.0096(10) C28 0.0365(13) 0.0323(13) 0.0524(15) 0.0059(11) 0.0264(12) 0.0050(11) C29 0.0490(16) 0.0313(14) 0.086(2) 0.0101(14) 0.0297(16) 0.0109(12) C30 0.0312(13) 0.0409(15) 0.078(2) -0.0152(14) 0.0244(13) 0.0093(12) C25 0.0396(14) 0.0541(18) 0.0496(15) -0.0060(13) 0.0044(12) 0.0222(14) O4 0.0736(14) 0.0633(14) 0.0508(12) 0.0002(11) 0.0380(11) 0.0123(12) O3 0.0725(13) 0.0337(10) 0.0375(9) 0.0048(8) 0.0118(9) 0.0119(10) O2 0.0637(13) 0.1055(19) 0.0476(12) -0.0249(12) 0.0380(11) -0.0380(14) C38 0.0558(17) 0.0518(17) 0.0423(14) 0.0130(13) 0.0163(13) -0.0097(14) C37 0.0638(19) 0.0422(16) 0.0472(16) -0.0038(13) 0.0132(14) 0.0076(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C2 1.315(2) . ? C1 C2 1.402(3) . ? C1 C10 1.434(3) . ? C1 C11 1.496(3) . ? C4 C3 1.373(3) . ? C4 C5 1.408(3) . ? C11 C12 1.389(3) . ? C11 C20 1.432(3) . ? C5 C6 1.415(3) . ? C5 C10 1.422(3) . ? C10 C9 1.418(3) . ? C3 C2 1.447(3) . ? C3 C21 1.484(3) . ? C6 C7 1.361(3) . ? C9 C8 1.373(3) . ? C19 C18 1.368(3) . ? C19 C20 1.422(3) . ? C20 C15 1.421(3) . ? C13 C14 1.373(3) . ? C13 C12 1.439(3) . ? C13 C27 1.496(3) . ? C14 C15 1.410(3) . ? C33 C12 1.507(3) . ? C33 N1 1.538(3) . ? N1 C36 1.494(3) . ? N1 C34 1.499(3) . ? N1 C35 1.501(3) . ? C21 C26 1.384(3) . ? C21 C22 1.390(3) . ? C7 C8 1.413(3) . ? C15 C16 1.416(3) . ? C27 C28 1.395(3) . ? C27 C32 1.396(3) . ? C16 C17 1.366(3) . ? C22 C23 1.385(3) . ? C18 C17 1.404(3) . ? C32 C31 1.390(3) . ? C31 C30 1.362(4) . ? C26 C25 1.389(4) . ? C23 C24 1.380(4) . ? C24 C25 1.377(4) . ? C28 C29 1.384(4) . ? C29 C30 1.387(4) . ? O3 C37 1.406(3) . ? O2 C38 1.371(4) . ? 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 121.82(18) . . ? C2 C1 C11 120.58(18) . . ? C10 C1 C11 117.58(17) . . ? C3 C4 C5 123.03(18) . . ? C12 C11 C20 120.02(17) . . ? C12 C11 C1 121.41(18) . . ? C20 C11 C1 118.34(17) . . ? C4 C5 C6 121.50(18) . . ? C4 C5 C10 118.01(18) . . ? C6 C5 C10 120.46(18) . . ? C9 C10 C5 116.55(18) . . ? C9 C10 C1 124.10(18) . . ? C5 C10 C1 119.35(17) . . ? C4 C3 C2 120.29(18) . . ? C4 C3 C21 117.63(18) . . ? C2 C3 C21 122.01(18) . . ? C7 C6 C5 121.57(19) . . ? C8 C9 C10 121.7(2) . . ? C18 C19 C20 120.9(2) . . ? C15 C20 C19 118.10(18) . . ? C15 C20 C11 119.29(18) . . ? C19 C20 C11 122.61(18) . . ? O1 C2 C1 123.10(18) . . ? O1 C2 C3 119.51(17) . . ? C1 C2 C3 117.36(18) . . ? C14 C13 C12 118.96(18) . . ? C14 C13 C27 117.41(18) . . ? C12 C13 C27 123.45(18) . . ? C13 C14 C15 122.17(18) . . ? C12 C33 N1 115.38(17) . . ? C36 N1 C34 108.59(19) . . ? C36 N1 C35 108.72(17) . . ? C34 N1 C35 108.40(18) . . ? C36 N1 C33 111.03(16) . . ? C34 N1 C33 112.34(16) . . ? C35 N1 C33 107.67(17) . . ? C26 C21 C22 118.4(2) . . ? C26 C21 C3 121.64(19) . . ? C22 C21 C3 119.4(2) . . ? C6 C7 C8 118.5(2) . . ? C11 C12 C13 120.14(18) . . ? C11 C12 C33 121.27(17) . . ? C13 C12 C33 118.54(17) . . ? C14 C15 C16 121.72(19) . . ? C14 C15 C20 118.96(18) . . ? C16 C15 C20 119.25(19) . . ? C9 C8 C7 121.2(2) . . ? C28 C27 C32 118.8(2) . . ? C28 C27 C13 120.41(19) . . ? C32 C27 C13 120.4(2) . . ? C17 C16 C15 121.1(2) . . ? C23 C22 C21 120.9(2) . . ? C19 C18 C17 120.8(2) . . ? C31 C32 C27 120.2(2) . . ? C16 C17 C18 119.8(2) . . ? C30 C31 C32 120.4(2) . . ? C21 C26 C25 120.7(2) . . ? C24 C23 C22 120.2(2) . . ? C25 C24 C23 119.6(2) . . ? C29 C28 C27 120.2(2) . . ? C28 C29 C30 120.2(3) . . ? C31 C30 C29 120.2(2) . . ? C24 C25 C26 120.3(3) . . ? 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 O2 H2 O1 0.84 1.80 2.624(2) 166.2 . O3 H3 O1 0.84 1.87 2.704(3) 172.6 . _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 28.39 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.291 _refine_diff_density_min -0.234 _refine_diff_density_rms 0.048