# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2005 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Albrecht Berkessel' 'Felix Cleeman' 'Johann Lex' 'Santanu Mukherjee' 'Thomas N. Muller' _publ_contact_author_name 'ProfD Albrecht Berkessel' _publ_contact_author_address ; Institut fur Organische Chemie der Universitat zu Koln Greinstrasse 4 Koeln D-50939 GERMANY ; _publ_contact_author_email BERKESSEL@UNI-KOELN.DE _publ_requested_journal 'Chemical Communications' _publ_section_title ; Second-Generation Organocatalysts for the Highly Enantioselective Dynamic Kinetic Resolution of Azlactones ; data_4a _database_code_depnum_ccdc_archive 'CCDC 256348' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H38 N4 O S' _chemical_formula_weight 370.59 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 monoclinic _symmetry_space_group_name_H-M p21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 11.702(1) _cell_length_b 13.351(1) _cell_length_c 14.156(1) _cell_angle_alpha 90. _cell_angle_beta 100.81(1) _cell_angle_gamma 90. _cell_volume 2172.4(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 10636 _cell_measurement_theta_min 2.08 _cell_measurement_theta_max 27.00 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.133 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 816 _exptl_absorpt_coefficient_mu 0.163 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method Phi/Omega-Scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10636 _diffrn_reflns_av_R_equivalents 0.0387 _diffrn_reflns_av_sigmaI/netI 0.0758 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.08 _diffrn_reflns_theta_max 27.00 _reflns_number_total 8211 _reflns_number_gt 6520 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius COLLECT' _computing_cell_refinement 'Nonius DENZO' _computing_data_reduction 'Nonius DENZO' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SCHAKAL99 (E. Keller, 1999)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0406P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment refall _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 -0.05(5) _refine_ls_number_reflns 8211 _refine_ls_number_parameters 756 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0655 _refine_ls_R_factor_gt 0.0439 _refine_ls_wR_factor_ref 0.0973 _refine_ls_wR_factor_gt 0.0887 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.023 _refine_ls_shift/su_max 0.105 _refine_ls_shift/su_mean 0.014 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 S1A S 0.57365(6) 0.33409(6) 0.85028(5) 0.03104(19) Uani 1 1 d . . . O2A O 0.48898(15) 0.65159(14) 0.77133(12) 0.0262(4) Uani 1 1 d . . . N3A N 0.60254(18) 0.63852(17) 0.91763(15) 0.0228(5) Uani 1 1 d . . . N4A N 0.19335(19) 0.37431(17) 0.64357(15) 0.0233(5) Uani 1 1 d . . . N5A N 0.43214(18) 0.35091(17) 0.68057(15) 0.0194(5) Uani 1 1 d . . . N6A N 0.56967(18) 0.47362(16) 0.71415(15) 0.0187(5) Uani 1 1 d . . . C7A C 0.5215(2) 0.38904(19) 0.74374(17) 0.0184(6) Uani 1 1 d . . . C8A C 0.3634(2) 0.2655(2) 0.70034(18) 0.0190(6) Uani 1 1 d . . . H8A H 0.358(2) 0.2676(17) 0.7639(18) 0.009(6) Uiso 1 1 d . . . C9A C 0.7442(2) 0.5846(2) 0.73205(17) 0.0197(6) Uani 1 1 d . . . C10A C 0.2404(2) 0.2724(2) 0.63935(18) 0.0194(6) Uani 1 1 d . . . H10A H 0.253(2) 0.2612(18) 0.5774(18) 0.012(6) Uiso 1 1 d . . . C11A C 0.5748(2) 0.61285(19) 0.82416(17) 0.0191(6) Uani 1 1 d . . . C12A C 0.6483(2) 0.5366(2) 0.78103(17) 0.0190(6) Uani 1 1 d . . . H12A H 0.687(2) 0.495(2) 0.8327(18) 0.017(7) Uiso 1 1 d . . . C13A C 0.5263(2) 0.7110(2) 0.95357(19) 0.0275(6) Uani 1 1 d . . . H13A H 0.545(2) 0.706(2) 1.0264(19) 0.021(7) Uiso 1 1 d . . . H13B H 0.438(2) 0.6853(19) 0.9271(18) 0.026(7) Uiso 1 1 d . . . C14A C 0.8295(3) 0.5023(2) 0.7174(2) 0.0270(6) Uani 1 1 d . . . H14A H 0.889(2) 0.530(2) 0.6906(18) 0.020(7) Uiso 1 1 d . . . H14B H 0.790(3) 0.452(3) 0.673(2) 0.042(9) Uiso 1 1 d . . . H14C H 0.865(3) 0.470(2) 0.786(2) 0.044(9) Uiso 1 1 d . . . C15A C 0.0783(3) 0.3844(3) 0.5816(2) 0.0323(7) Uani 1 1 d . . . H15A H 0.014(3) 0.352(3) 0.607(2) 0.049(10) Uiso 1 1 d . . . H15B H 0.083(3) 0.353(2) 0.517(2) 0.040(9) Uiso 1 1 d . . . H15C H 0.060(2) 0.457(2) 0.5709(19) 0.030(8) Uiso 1 1 d . . . C16A C 0.4189(3) 0.1648(2) 0.6830(2) 0.0274(6) Uani 1 1 d . . . H16A H 0.505(3) 0.165(2) 0.720(2) 0.036(8) Uiso 1 1 d . . . H16B H 0.420(2) 0.158(2) 0.616(2) 0.026(7) Uiso 1 1 d . . . C17A C 0.6948(3) 0.6334(2) 0.6357(2) 0.0266(6) Uani 1 1 d . . . H17A H 0.641(3) 0.686(2) 0.6463(19) 0.031(8) Uiso 1 1 d . . . H17B H 0.658(3) 0.588(2) 0.591(2) 0.027(8) Uiso 1 1 d . . . H17C H 0.763(2) 0.664(2) 0.6061(19) 0.030(7) Uiso 1 1 d . . . C18A C 0.3453(3) 0.0784(2) 0.7102(2) 0.0313(7) Uani 1 1 d . . . H18A H 0.386(3) 0.009(3) 0.697(2) 0.057(10) Uiso 1 1 d . . . H18B H 0.347(2) 0.0805(18) 0.7845(18) 0.017(6) Uiso 1 1 d . . . C19A C 0.2215(3) 0.0841(2) 0.6532(2) 0.0311(7) Uani 1 1 d . . . H19A H 0.172(2) 0.029(2) 0.6730(17) 0.019(7) Uiso 1 1 d . . . H19B H 0.217(3) 0.076(2) 0.579(2) 0.049(9) Uiso 1 1 d . . . C20A C 0.1658(2) 0.1860(2) 0.6658(2) 0.0262(6) Uani 1 1 d . . . H20A H 0.089(3) 0.190(2) 0.625(2) 0.032(8) Uiso 1 1 d . . . H20B H 0.153(2) 0.196(2) 0.733(2) 0.038(8) Uiso 1 1 d . . . C21A C 0.8109(3) 0.6653(2) 0.7977(2) 0.0288(7) Uani 1 1 d . . . H21A H 0.853(3) 0.636(3) 0.861(2) 0.056(10) Uiso 1 1 d . . . H21B H 0.761(3) 0.721(2) 0.8103(19) 0.034(8) Uiso 1 1 d . . . H21C H 0.876(2) 0.699(2) 0.7667(18) 0.027(7) Uiso 1 1 d . . . C22A C 0.6906(3) 0.5907(3) 0.9915(2) 0.0376(8) Uani 1 1 d . . . H22A H 0.739(3) 0.539(2) 0.958(2) 0.038(8) Uiso 1 1 d . . . H22B H 0.645(2) 0.553(2) 1.034(2) 0.024(7) Uiso 1 1 d . . . C23A C 0.7756(3) 0.6651(4) 1.0470(3) 0.0600(12) Uani 1 1 d . . . H23A H 0.831(4) 0.628(4) 1.096(4) 0.101(16) Uiso 1 1 d . . . H23B H 0.738(3) 0.713(3) 1.083(2) 0.043(9) Uiso 1 1 d . . . H23C H 0.821(3) 0.708(3) 1.000(3) 0.074(12) Uiso 1 1 d . . . C24A C 0.1893(3) 0.4100(3) 0.7396(2) 0.0303(7) Uani 1 1 d . . . H24A H 0.161(3) 0.478(3) 0.735(2) 0.033(8) Uiso 1 1 d . . . H24B H 0.265(3) 0.416(2) 0.778(2) 0.027(8) Uiso 1 1 d . . . H24C H 0.128(3) 0.366(2) 0.768(2) 0.034(8) Uiso 1 1 d . . . C25A C 0.5453(5) 0.8172(3) 0.9237(3) 0.0543(10) Uani 1 1 d . . . H25A H 0.494(3) 0.868(3) 0.950(3) 0.062(11) Uiso 1 1 d . . . H25B H 0.521(3) 0.829(3) 0.851(3) 0.070(12) Uiso 1 1 d . . . H25C H 0.632(3) 0.829(3) 0.945(2) 0.057(11) Uiso 1 1 d . . . H1A H 0.528(2) 0.5056(19) 0.6682(19) 0.016(7) Uiso 1 1 d . . . H2A H 0.404(2) 0.389(2) 0.640(2) 0.023(8) Uiso 1 1 d . . . S1B S 1.04062(6) 0.70832(5) 0.63954(4) 0.02635(17) Uani 1 1 d . . . O2B O 1.38252(15) 0.52482(13) 0.54489(12) 0.0214(4) Uani 1 1 d . . . N3B N 1.26269(19) 0.65884(17) 0.63973(14) 0.0197(5) Uani 1 1 d . . . N4B N 1.22208(19) 0.70171(17) 0.78568(14) 0.0208(5) Uani 1 1 d . . . C5B C 1.2438(2) 0.65814(19) 0.53557(16) 0.0163(5) Uani 1 1 d . . . H5B H 1.160(2) 0.6669(18) 0.5137(16) 0.013(6) Uiso 1 1 d . . . N6B N 1.22441(18) 0.50816(15) 0.42742(14) 0.0204(5) Uani 1 1 d . . . C7B C 1.2759(2) 0.4164(2) 0.3952(2) 0.0225(6) Uani 1 1 d . . . H7B1 H 1.211(2) 0.3762(18) 0.3624(17) 0.015(6) Uiso 1 1 d . . . H7B2 H 1.315(2) 0.3768(19) 0.4510(19) 0.020(7) Uiso 1 1 d . . . N8B N 1.2400(2) 0.59930(16) 0.96409(15) 0.0261(5) Uani 1 1 d . . . C9B C 1.2034(2) 0.7047(2) 0.95732(17) 0.0211(5) Uani 1 1 d . . . H9B H 1.276(2) 0.747(2) 0.9744(19) 0.029(7) Uiso 1 1 d . . . C10B C 1.2868(2) 0.55784(19) 0.50316(17) 0.0185(6) Uani 1 1 d . . . C11B C 1.2788(3) 0.7458(2) 0.38529(19) 0.0233(6) Uani 1 1 d . . . H11A H 1.190(3) 0.749(2) 0.354(2) 0.032(8) Uiso 1 1 d . . . H11B H 1.310(2) 0.686(2) 0.3602(19) 0.030(8) Uiso 1 1 d . . . H11C H 1.309(3) 0.805(3) 0.358(2) 0.043(9) Uiso 1 1 d . . . C12B C 1.1047(2) 0.5302(2) 0.37757(19) 0.0249(6) Uani 1 1 d . . . H12B H 1.077(3) 0.590(2) 0.411(2) 0.035(8) Uiso 1 1 d . . . H12C H 1.052(2) 0.473(2) 0.3868(18) 0.027(7) Uiso 1 1 d . . . C13B C 1.3036(2) 0.74942(19) 0.49474(17) 0.0199(6) Uani 1 1 d . . . C14B C 1.1344(3) 0.8490(2) 0.84988(19) 0.0288(7) Uani 1 1 d . . . H14D H 1.219(3) 0.885(2) 0.870(2) 0.038(8) Uiso 1 1 d . . . H14E H 1.105(2) 0.869(2) 0.777(2) 0.032(8) Uiso 1 1 d . . . C15B C 1.0942(3) 0.5492(2) 0.2707(2) 0.0313(7) Uani 1 1 d . . . H15D H 1.011(3) 0.569(2) 0.242(2) 0.039(8) Uiso 1 1 d . . . H15E H 1.119(2) 0.485(2) 0.237(2) 0.031(8) Uiso 1 1 d . . . H15F H 1.144(3) 0.612(3) 0.253(3) 0.070(12) Uiso 1 1 d . . . C16B C 1.4348(2) 0.7494(2) 0.5313(2) 0.0257(6) Uani 1 1 d . . . H16C H 1.469(2) 0.807(2) 0.5094(19) 0.025(8) Uiso 1 1 d . . . H16D H 1.474(2) 0.690(2) 0.5090(19) 0.025(7) Uiso 1 1 d . . . H16E H 1.458(2) 0.751(2) 0.607(2) 0.030(7) Uiso 1 1 d . . . C17B C 1.3659(3) 0.4385(3) 0.3341(2) 0.0309(7) Uani 1 1 d . . . H17D H 1.396(2) 0.376(2) 0.311(2) 0.027(8) Uiso 1 1 d . . . H17E H 1.432(3) 0.473(3) 0.371(2) 0.040(9) Uiso 1 1 d . . . H17F H 1.331(2) 0.475(2) 0.277(2) 0.028(7) Uiso 1 1 d . . . C18B C 1.1200(2) 0.7356(2) 1.0239(2) 0.0286(7) Uani 1 1 d . . . H18C H 1.150(2) 0.719(2) 1.090(2) 0.027(7) Uiso 1 1 d . . . H18D H 1.042(2) 0.697(2) 0.9997(19) 0.033(8) Uiso 1 1 d . . . C19B C 1.0977(3) 0.8483(2) 1.0194(2) 0.0314(7) Uani 1 1 d . . . H19C H 1.043(3) 0.863(2) 1.061(2) 0.031(8) Uiso 1 1 d . . . H19D H 1.171(3) 0.883(3) 1.048(2) 0.051(10) Uiso 1 1 d . . . C20B C 1.1817(2) 0.68929(19) 0.69051(17) 0.0197(6) Uani 1 1 d . . . C21B C 1.1507(2) 0.7357(2) 0.85388(17) 0.0232(6) Uani 1 1 d . . . H21D H 1.073(2) 0.7037(18) 0.8322(15) 0.008(6) Uiso 1 1 d . . . C22B C 1.2532(3) 0.8457(2) 0.5286(2) 0.0265(6) Uani 1 1 d . . . H22C H 1.293(2) 0.907(2) 0.501(2) 0.025(7) Uiso 1 1 d . . . H22D H 1.273(2) 0.857(2) 0.597(2) 0.027(7) Uiso 1 1 d . . . H22E H 1.174(3) 0.851(2) 0.506(2) 0.029(8) Uiso 1 1 d . . . C23B C 1.0529(3) 0.8830(3) 0.9169(2) 0.0340(8) Uani 1 1 d . . . H23D H 1.047(3) 0.953(3) 0.912(2) 0.052(11) Uiso 1 1 d . . . H23E H 0.974(2) 0.8539(19) 0.8920(18) 0.021(7) Uiso 1 1 d . . . C24B C 1.3113(3) 0.5759(3) 1.0581(2) 0.0357(8) Uani 1 1 d . . . H24D H 1.260(3) 0.568(2) 1.107(2) 0.029(8) Uiso 1 1 d . . . H24E H 1.367(3) 0.629(3) 1.082(2) 0.039(9) Uiso 1 1 d . . . H24F H 1.355(3) 0.513(2) 1.054(2) 0.031(8) Uiso 1 1 d . . . C25B C 1.1443(3) 0.5286(3) 0.9410(2) 0.0388(8) Uani 1 1 d . . . H25D H 1.084(3) 0.528(3) 0.986(2) 0.047(9) Uiso 1 1 d . . . H25E H 1.178(2) 0.460(2) 0.940(2) 0.030(8) Uiso 1 1 d . . . H25F H 1.096(3) 0.544(2) 0.873(2) 0.035(8) Uiso 1 1 d . . . H1B H 1.335(3) 0.648(2) 0.670(2) 0.032(8) Uiso 1 1 d . . . H2B H 1.290(2) 0.686(2) 0.8090(19) 0.027(8) 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 S1A 0.0299(4) 0.0342(4) 0.0252(3) 0.0119(3) -0.0047(3) -0.0093(3) O2A 0.0209(10) 0.0337(12) 0.0231(9) 0.0002(8) 0.0016(8) 0.0049(9) N3A 0.0165(11) 0.0298(13) 0.0214(11) -0.0053(9) 0.0018(9) 0.0015(10) N4A 0.0183(12) 0.0291(13) 0.0216(11) -0.0001(9) 0.0015(9) -0.0028(10) N5A 0.0176(11) 0.0204(13) 0.0191(11) 0.0033(10) 0.0006(9) -0.0036(10) N6A 0.0181(11) 0.0183(12) 0.0181(11) 0.0026(9) -0.0005(9) -0.0009(10) C7A 0.0167(13) 0.0219(15) 0.0170(12) -0.0018(10) 0.0042(10) -0.0008(11) C8A 0.0194(14) 0.0207(15) 0.0181(13) 0.0001(11) 0.0063(11) -0.0020(11) C9A 0.0143(13) 0.0207(14) 0.0237(13) -0.0019(11) 0.0028(10) -0.0020(11) C10A 0.0194(14) 0.0234(16) 0.0160(13) -0.0037(11) 0.0050(11) -0.0055(11) C11A 0.0154(13) 0.0210(15) 0.0209(13) 0.0004(10) 0.0031(11) -0.0028(11) C12A 0.0184(13) 0.0221(14) 0.0151(12) 0.0010(10) -0.0004(10) -0.0003(11) C13A 0.0267(15) 0.0313(17) 0.0260(14) -0.0084(13) 0.0089(11) 0.0016(14) C14A 0.0255(16) 0.0259(17) 0.0307(16) 0.0001(13) 0.0087(13) 0.0030(13) C15A 0.0229(16) 0.037(2) 0.0348(18) 0.0080(14) -0.0012(13) 0.0008(14) C16A 0.0291(17) 0.0217(15) 0.0331(16) 0.0010(12) 0.0100(13) -0.0010(12) C17A 0.0236(16) 0.0273(17) 0.0285(15) 0.0030(13) 0.0035(12) -0.0055(14) C18A 0.0340(17) 0.0212(16) 0.0405(18) 0.0027(13) 0.0117(14) -0.0013(13) C19A 0.0318(17) 0.0235(17) 0.0394(17) -0.0035(13) 0.0102(14) -0.0092(14) C20A 0.0231(15) 0.0256(17) 0.0302(15) -0.0026(12) 0.0062(12) -0.0070(12) C21A 0.0228(15) 0.0315(18) 0.0329(16) -0.0071(13) 0.0075(13) -0.0097(14) C22A 0.0334(18) 0.051(2) 0.0243(15) -0.0065(15) -0.0043(14) 0.0139(16) C23A 0.0287(19) 0.119(4) 0.0302(18) -0.032(2) -0.0003(15) 0.001(2) C24A 0.0300(17) 0.0285(19) 0.0327(16) -0.0024(13) 0.0063(14) 0.0000(14) C25A 0.078(3) 0.036(2) 0.056(2) -0.0098(17) 0.031(2) 0.006(2) S1B 0.0175(3) 0.0398(4) 0.0220(3) -0.0004(3) 0.0040(3) 0.0011(3) O2B 0.0187(9) 0.0246(10) 0.0196(9) 0.0026(7) -0.0001(7) 0.0014(8) N3B 0.0156(11) 0.0275(13) 0.0158(10) 0.0018(9) 0.0024(9) 0.0042(10) N4B 0.0166(11) 0.0297(13) 0.0157(10) -0.0004(9) 0.0023(9) 0.0045(11) C5B 0.0129(13) 0.0226(14) 0.0132(11) 0.0007(10) 0.0016(10) 0.0018(11) N6B 0.0198(12) 0.0198(12) 0.0203(11) -0.0029(9) 0.0003(9) 0.0036(9) C7B 0.0232(15) 0.0203(15) 0.0221(14) -0.0020(11) -0.0005(12) 0.0024(12) N8B 0.0332(14) 0.0201(13) 0.0257(12) -0.0004(9) 0.0072(10) -0.0014(10) C9B 0.0220(13) 0.0241(15) 0.0174(12) -0.0025(11) 0.0046(10) -0.0017(13) C10B 0.0190(14) 0.0231(15) 0.0142(12) 0.0055(10) 0.0050(10) 0.0001(11) C11B 0.0276(16) 0.0222(16) 0.0206(13) 0.0029(11) 0.0056(11) 0.0008(13) C12B 0.0187(14) 0.0294(17) 0.0245(14) -0.0052(12) -0.0017(11) 0.0016(13) C13B 0.0194(13) 0.0210(14) 0.0192(13) -0.0003(10) 0.0036(10) 0.0007(11) C14B 0.0328(16) 0.0329(18) 0.0203(14) -0.0006(12) 0.0046(12) 0.0093(14) C15B 0.0315(17) 0.0345(19) 0.0229(14) -0.0036(13) -0.0078(13) 0.0041(15) C16B 0.0225(15) 0.0257(18) 0.0286(15) 0.0039(12) 0.0043(12) -0.0062(13) C17B 0.0353(18) 0.0336(19) 0.0244(15) 0.0012(14) 0.0068(14) 0.0115(15) C18B 0.0210(15) 0.042(2) 0.0225(14) -0.0061(12) 0.0023(11) -0.0002(13) C19B 0.0289(16) 0.043(2) 0.0221(14) -0.0084(13) 0.0054(13) 0.0089(15) C20B 0.0224(13) 0.0189(15) 0.0189(12) 0.0002(10) 0.0065(10) -0.0011(11) C21B 0.0208(14) 0.0308(17) 0.0174(12) -0.0047(11) 0.0018(11) 0.0026(12) C22B 0.0292(16) 0.0263(17) 0.0238(15) -0.0007(12) 0.0040(12) -0.0007(14) C23B 0.0328(18) 0.040(2) 0.0262(16) -0.0040(13) -0.0012(13) 0.0127(15) C24B 0.050(2) 0.0299(19) 0.0267(16) 0.0045(14) 0.0057(15) 0.0083(18) C25B 0.052(2) 0.029(2) 0.0372(18) -0.0048(14) 0.0136(17) -0.0140(17) _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 S1A C7A 1.685(2) . ? O2A C11A 1.247(3) . ? N3A C11A 1.346(3) . ? N3A C13A 1.470(3) . ? N3A C22A 1.469(3) . ? N4A C24A 1.450(4) . ? N4A C15A 1.469(3) . ? N4A C10A 1.473(3) . ? N5A C7A 1.342(3) . ? N5A C8A 1.453(3) . ? N6A C7A 1.363(3) . ? N6A C12A 1.458(3) . ? C8A C16A 1.533(4) . ? C8A C10A 1.536(3) . ? C9A C14A 1.525(4) . ? C9A C17A 1.524(4) . ? C9A C21A 1.537(4) . ? C9A C12A 1.562(4) . ? C10A C20A 1.534(4) . ? C11A C12A 1.531(4) . ? C13A C25A 1.507(5) . ? C16A C18A 1.531(4) . ? C18A C19A 1.523(4) . ? C19A C20A 1.533(4) . ? C22A C23A 1.516(5) . ? S1B C20B 1.692(3) . ? O2B C10B 1.245(3) . ? N3B C20B 1.355(3) . ? N3B C5B 1.449(3) . ? N4B C20B 1.352(3) . ? N4B C21B 1.463(3) . ? C5B C10B 1.531(4) . ? C5B C13B 1.569(4) . ? N6B C10B 1.352(3) . ? N6B C12B 1.475(3) . ? N6B C7B 1.475(3) . ? C7B C17B 1.511(4) . ? N8B C25B 1.455(4) . ? N8B C9B 1.469(4) . ? N8B C24B 1.466(4) . ? C9B C21B 1.535(3) . ? C9B C18B 1.535(4) . ? C11B C13B 1.523(3) . ? C12B C15B 1.516(4) . ? C13B C16B 1.526(4) . ? C13B C22B 1.529(4) . ? C14B C21B 1.524(4) . ? C14B C23B 1.535(4) . ? C18B C19B 1.526(4) . ? C19B C23B 1.520(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 C11A N3A C13A 117.3(2) . . ? C11A N3A C22A 126.6(2) . . ? C13A N3A C22A 115.4(2) . . ? C24A N4A C15A 110.1(2) . . ? C24A N4A C10A 114.8(2) . . ? C15A N4A C10A 111.6(2) . . ? C7A N5A C8A 124.0(2) . . ? C7A N6A C12A 121.7(2) . . ? N5A C7A N6A 115.2(2) . . ? N5A C7A S1A 122.5(2) . . ? N6A C7A S1A 122.31(18) . . ? N5A C8A C16A 113.0(2) . . ? N5A C8A C10A 109.8(2) . . ? C16A C8A C10A 110.1(2) . . ? C14A C9A C17A 109.6(2) . . ? C14A C9A C21A 108.4(2) . . ? C17A C9A C21A 107.8(2) . . ? C14A C9A C12A 107.9(2) . . ? C17A C9A C12A 112.9(2) . . ? C21A C9A C12A 110.1(2) . . ? N4A C10A C20A 116.8(2) . . ? N4A C10A C8A 110.5(2) . . ? C20A C10A C8A 109.5(2) . . ? O2A C11A N3A 120.2(2) . . ? O2A C11A C12A 119.1(2) . . ? N3A C11A C12A 120.8(2) . . ? N6A C12A C11A 108.0(2) . . ? N6A C12A C9A 111.5(2) . . ? C11A C12A C9A 114.1(2) . . ? N3A C13A C25A 113.0(3) . . ? C8A C16A C18A 110.2(2) . . ? C19A C18A C16A 110.7(2) . . ? C18A C19A C20A 111.5(2) . . ? C19A C20A C10A 111.4(2) . . ? N3A C22A C23A 112.9(3) . . ? C20B N3B C5B 123.6(2) . . ? C20B N4B C21B 124.0(2) . . ? N3B C5B C10B 108.34(19) . . ? N3B C5B C13B 112.10(19) . . ? C10B C5B C13B 112.0(2) . . ? C10B N6B C12B 127.2(2) . . ? C10B N6B C7B 117.5(2) . . ? C12B N6B C7B 115.1(2) . . ? N6B C7B C17B 112.5(2) . . ? C25B N8B C9B 113.8(2) . . ? C25B N8B C24B 110.4(3) . . ? C9B N8B C24B 111.9(2) . . ? N8B C9B C21B 112.4(2) . . ? N8B C9B C18B 115.4(2) . . ? C21B C9B C18B 109.0(2) . . ? O2B C10B N6B 120.4(2) . . ? O2B C10B C5B 119.0(2) . . ? N6B C10B C5B 120.5(2) . . ? N6B C12B C15B 113.8(2) . . ? C11B C13B C16B 109.5(2) . . ? C11B C13B C22B 109.5(2) . . ? C16B C13B C22B 108.5(2) . . ? C11B C13B C5B 109.7(2) . . ? C16B C13B C5B 111.4(2) . . ? C22B C13B C5B 108.2(2) . . ? C21B C14B C23B 111.0(3) . . ? C19B C18B C9B 111.2(3) . . ? C18B C19B C23B 111.5(2) . . ? N3B C20B N4B 114.6(2) . . ? N3B C20B S1B 122.84(18) . . ? N4B C20B S1B 122.5(2) . . ? N4B C21B C14B 111.5(2) . . ? N4B C21B C9B 111.6(2) . . ? C14B C21B C9B 109.2(2) . . ? C19B C23B C14B 110.9(2) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.308 _refine_diff_density_min -0.277 _refine_diff_density_rms 0.047