# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Ying-Chun Chen.' 'Qian Chai.' 'Hai-Lei Cui.' 'Li-sheng Ding.' 'Bang-Jing Li.' 'Tian-Yu Liu.' 'Jun Long.' 'Yong Wu.' _publ_contact_author_name 'Ying-Chun Chen' _publ_contact_author_address ; Department of Medicinal Chemistry West China School of Pharmacy Chengdu 610041 CHINA ; _publ_contact_author_email YCCHENHUAXI@YAHOO.COM.CN _publ_requested_journal 'Chemical Communications' _publ_section_title ; Organocatalytic Asymmetric Friedel-Crafts Alkylation/Cascade Reactions of Naphthols and Nitroolefins ; data_4ahtosylate _database_code_depnum_ccdc_archive 'CCDC 642668' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H19 N O5 S2' _chemical_formula_weight 453.51 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 P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 10.090(2) _cell_length_b 10.883(2) _cell_length_c 20.027(4) _cell_angle_alpha 90.00 _cell_angle_beta 101.95(2) _cell_angle_gamma 90.00 _cell_volume 2151.5(7) _cell_formula_units_Z 4 _cell_measurement_temperature 290(2) _cell_measurement_reflns_used 33 _cell_measurement_theta_min 4.63 _cell_measurement_theta_max 13.81 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.400 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 944 _exptl_absorpt_coefficient_mu 0.283 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9296 _exptl_absorpt_correction_T_max 0.9837 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 290(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Siemens P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 2.94 _diffrn_reflns_number 9211 _diffrn_reflns_av_R_equivalents 0.0192 _diffrn_reflns_av_sigmaI/netI 0.0768 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.04 _diffrn_reflns_theta_max 25.50 _reflns_number_total 7999 _reflns_number_gt 4603 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens 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^)+(0.0340P)^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 constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0058(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.02(6) _refine_ls_number_reflns 7999 _refine_ls_number_parameters 562 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0856 _refine_ls_R_factor_gt 0.0439 _refine_ls_wR_factor_ref 0.0868 _refine_ls_wR_factor_gt 0.0786 _refine_ls_goodness_of_fit_ref 0.886 _refine_ls_restrained_S_all 0.885 _refine_ls_shift/su_max 0.001 _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 S1 S 0.44553(10) 0.34966(10) 0.93968(5) 0.0527(3) Uani 1 1 d . . . S2 S 0.55325(14) 0.28877(12) 0.71463(7) 0.0876(4) Uani 1 1 d . . . O1 O 0.4316(2) 0.3389(2) 0.85880(11) 0.0482(6) Uani 1 1 d . . . O2 O 0.5800(2) 0.3062(2) 0.96498(13) 0.0656(8) Uani 1 1 d . . . O3 O 0.4067(3) 0.4701(2) 0.95602(13) 0.0638(8) Uani 1 1 d . . . O4 O 0.7423(3) 0.6899(3) 0.82499(18) 0.1020(13) Uani 1 1 d . . . O5 O 0.8502(3) 0.5227(4) 0.84654(16) 0.0938(11) Uani 1 1 d . . . N1 N 0.7467(4) 0.5822(4) 0.83817(18) 0.0626(10) Uani 1 1 d . . . C1 C 0.2296(4) 0.2770(4) 0.99106(19) 0.0577(11) Uani 1 1 d . . . H1 H 0.2234 0.3582 1.0047 0.069 Uiso 1 1 calc R . . C2 C 0.1380(4) 0.1899(4) 1.0040(2) 0.0649(12) Uani 1 1 d . . . H2 H 0.0710 0.2130 1.0271 0.078 Uiso 1 1 calc R . . C3 C 0.1443(4) 0.0711(4) 0.98355(18) 0.0511(10) Uani 1 1 d . . . C4 C 0.2469(4) 0.0370(4) 0.95143(19) 0.0601(11) Uani 1 1 d . . . H4 H 0.2536 -0.0443 0.9381 0.072 Uiso 1 1 calc R . . C5 C 0.3399(4) 0.1223(4) 0.9388(2) 0.0569(11) Uani 1 1 d . . . H5 H 0.4093 0.0984 0.9175 0.068 Uiso 1 1 calc R . . C6 C 0.3298(4) 0.2418(3) 0.95778(18) 0.0433(9) Uani 1 1 d . . . C7 C 0.0407(4) -0.0222(4) 0.9943(2) 0.0782(14) Uani 1 1 d . . . H7A H -0.0021 0.0050 1.0302 0.094 Uiso 1 1 calc R . . H7B H 0.0844 -0.0997 1.0065 0.094 Uiso 1 1 calc R . . H7C H -0.0264 -0.0313 0.9529 0.094 Uiso 1 1 calc R . . C8 C 0.3318(4) 0.4069(3) 0.81288(18) 0.0462(10) Uani 1 1 d . . . C9 C 0.1958(4) 0.3771(4) 0.80830(19) 0.0625(12) Uani 1 1 d . . . H9 H 0.1708 0.3181 0.8370 0.075 Uiso 1 1 calc R . . C10 C 0.1006(4) 0.4356(4) 0.7613(2) 0.0683(13) Uani 1 1 d . . . H10 H 0.0095 0.4178 0.7588 0.082 Uiso 1 1 calc R . . C11 C 0.1364(4) 0.5225(4) 0.71633(18) 0.0541(10) Uani 1 1 d . . . C12 C 0.0363(4) 0.5826(4) 0.6667(2) 0.0741(14) Uani 1 1 d . . . H12 H -0.0548 0.5651 0.6642 0.089 Uiso 1 1 calc R . . C13 C 0.0727(4) 0.6654(5) 0.6231(2) 0.0815(14) Uani 1 1 d . . . H13 H 0.0059 0.7047 0.5914 0.098 Uiso 1 1 calc R . . C14 C 0.2089(4) 0.6924(4) 0.6251(2) 0.0770(14) Uani 1 1 d . . . H14 H 0.2326 0.7484 0.5945 0.092 Uiso 1 1 calc R . . C15 C 0.3065(4) 0.6358(4) 0.67234(19) 0.0599(11) Uani 1 1 d . . . H15 H 0.3969 0.6538 0.6731 0.072 Uiso 1 1 calc R . . C16 C 0.2750(4) 0.5498(3) 0.72072(18) 0.0443(9) Uani 1 1 d . . . C17 C 0.3759(3) 0.4917(3) 0.77147(17) 0.0403(8) Uani 1 1 d . . . C18 C 0.5243(3) 0.5208(3) 0.77271(16) 0.0404(8) Uani 1 1 d . . . H18 H 0.5264 0.6057 0.7566 0.049 Uiso 1 1 calc R . . C19 C 0.5795(3) 0.4423(3) 0.72242(19) 0.0440(10) Uani 1 1 d . . . C20 C 0.6670(3) 0.4828(3) 0.67869(16) 0.0366(9) Uani 1 1 d . . . H20 H 0.6938 0.5635 0.6739 0.044 Uiso 1 1 calc R . . C21 C 0.7039(5) 0.3857(6) 0.6459(3) 0.0925(18) Uani 1 1 d . . . H21 H 0.7623 0.3944 0.6159 0.111 Uiso 1 1 calc R . . C22 C 0.6544(4) 0.2760(5) 0.6575(2) 0.0779(15) Uani 1 1 d . . . H22 H 0.6728 0.2030 0.6371 0.094 Uiso 1 1 calc R . . C23 C 0.6194(3) 0.5169(4) 0.84322(16) 0.0490(9) Uani 1 1 d . . . H23A H 0.5771 0.5567 0.8768 0.059 Uiso 1 1 calc R . . H23B H 0.6391 0.4324 0.8572 0.059 Uiso 1 1 calc R . . S1' S 0.98623(10) 0.13866(11) 0.57704(5) 0.0610(3) Uani 1 1 d . . . S2' S 0.89180(12) 0.17279(11) 0.82464(6) 0.0761(4) Uani 1 1 d . . . N1' N 0.6783(4) -0.1154(4) 0.66360(19) 0.0693(10) Uani 1 1 d . . . O1' O 1.0284(2) 0.1670(2) 0.65770(11) 0.0526(6) Uani 1 1 d . . . O2' O 0.9021(3) 0.2401(3) 0.55214(14) 0.0794(9) Uani 1 1 d . . . O3' O 0.9365(3) 0.0156(3) 0.56847(13) 0.0790(9) Uani 1 1 d . . . O4' O 0.6366(3) -0.0254(3) 0.6302(2) 0.1094(13) Uani 1 1 d . . . O5' O 0.6064(3) -0.1996(3) 0.67165(19) 0.1104(13) Uani 1 1 d . . . C1' C 1.1956(4) 0.2615(4) 0.5418(2) 0.0707(13) Uani 1 1 d . . . H1' H 1.1528 0.3332 0.5512 0.085 Uiso 1 1 calc R . . C2' C 1.3161(5) 0.2667(5) 0.5209(2) 0.0781(14) Uani 1 1 d . . . H2' H 1.3546 0.3432 0.5168 0.094 Uiso 1 1 calc R . . C3' C 1.3817(4) 0.1652(6) 0.5062(2) 0.0759(14) Uani 1 1 d . . . C4' C 1.3247(5) 0.0535(5) 0.5133(2) 0.0850(15) Uani 1 1 d . . . H4' H 1.3689 -0.0175 0.5041 0.102 Uiso 1 1 calc R . . C5' C 1.2012(5) 0.0436(4) 0.5344(2) 0.0736(13) Uani 1 1 d . . . H5' H 1.1628 -0.0330 0.5386 0.088 Uiso 1 1 calc R . . C6' C 1.1385(4) 0.1483(4) 0.54859(18) 0.0507(10) Uani 1 1 d . . . C7' C 1.5158(4) 0.1686(6) 0.4830(2) 0.1122(19) Uani 1 1 d . . . H7'1 H 1.5886 0.1547 0.5215 0.135 Uiso 1 1 calc R . . H7'2 H 1.5269 0.2475 0.4634 0.135 Uiso 1 1 calc R . . H7'3 H 1.5166 0.1057 0.4495 0.135 Uiso 1 1 calc R . . C8' C 1.1044(4) 0.0765(3) 0.70097(18) 0.0477(10) Uani 1 1 d . . . C9' C 1.2457(4) 0.0846(4) 0.70978(19) 0.0596(12) Uani 1 1 d . . . H9' H 1.2848 0.1449 0.6872 0.072 Uiso 1 1 calc R . . C10' C 1.3246(4) 0.0037(4) 0.75156(19) 0.0668(12) Uani 1 1 d . . . H10' H 1.4183 0.0084 0.7570 0.080 Uiso 1 1 calc R . . C11' C 1.2681(4) -0.0870(4) 0.7868(2) 0.0509(10) Uani 1 1 d . . . C12' C 1.3494(4) -0.1712(4) 0.8295(2) 0.0619(12) Uani 1 1 d . . . H12' H 1.4429 -0.1689 0.8335 0.074 Uiso 1 1 calc R . . C13' C 1.2942(5) -0.2567(4) 0.8654(2) 0.0669(12) Uani 1 1 d . . . H13' H 1.3497 -0.3120 0.8937 0.080 Uiso 1 1 calc R . . C14' C 1.1542(4) -0.2607(4) 0.8595(2) 0.0618(11) Uani 1 1 d . . . H14' H 1.1161 -0.3196 0.8835 0.074 Uiso 1 1 calc R . . C15' C 1.0738(4) -0.1797(3) 0.81919(18) 0.0540(10) Uani 1 1 d . . . H15' H 0.9809 -0.1826 0.8171 0.065 Uiso 1 1 calc R . . C16' C 1.1250(4) -0.0904(3) 0.77989(18) 0.0449(9) Uani 1 1 d . . . C17' C 1.0415(3) -0.0059(3) 0.73493(18) 0.0443(9) Uani 1 1 d . . . C18' C 0.8867(3) -0.0039(3) 0.72458(18) 0.0486(9) Uani 1 1 d . . . H18' H 0.8558 0.0591 0.6899 0.058 Uiso 1 1 calc R . . C19' C 0.8364(3) 0.0361(3) 0.78655(18) 0.0454(9) Uani 1 1 d . . . C20' C 0.7390(4) -0.0129(4) 0.8172(2) 0.0563(11) Uani 1 1 d . . . H20' H 0.6950 -0.0867 0.8038 0.068 Uiso 1 1 calc R . . C21' C 0.7125(5) 0.0598(5) 0.8708(2) 0.0758(14) Uani 1 1 d . . . H21' H 0.6492 0.0390 0.8967 0.091 Uiso 1 1 calc R . . C22' C 0.7876(4) 0.1622(5) 0.8807(2) 0.0735(13) Uani 1 1 d . . . H22' H 0.7831 0.2202 0.9143 0.088 Uiso 1 1 calc R . . C23' C 0.8259(3) -0.1250(4) 0.69341(19) 0.0589(11) Uani 1 1 d . . . H23C H 0.8728 -0.1502 0.6580 0.071 Uiso 1 1 calc R . . H23D H 0.8402 -0.1880 0.7284 0.071 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0580(6) 0.0511(7) 0.0505(6) 0.0027(5) 0.0144(5) -0.0059(6) S2 0.0986(10) 0.0699(8) 0.1000(10) -0.0062(7) 0.0335(8) -0.0109(8) O1 0.0464(14) 0.0541(16) 0.0456(14) 0.0030(13) 0.0130(11) -0.0031(13) O2 0.0487(16) 0.084(2) 0.0620(17) 0.0053(15) 0.0061(13) -0.0038(15) O3 0.090(2) 0.0403(16) 0.0659(18) -0.0031(13) 0.0264(16) -0.0089(15) O4 0.100(3) 0.077(3) 0.116(3) 0.025(2) -0.008(2) -0.046(2) O5 0.0476(19) 0.130(3) 0.104(3) -0.010(2) 0.0166(18) -0.011(2) N1 0.047(2) 0.084(3) 0.053(2) -0.001(2) -0.0003(18) -0.021(2) C1 0.075(3) 0.035(2) 0.070(3) -0.005(2) 0.031(2) 0.006(2) C2 0.066(3) 0.062(3) 0.077(3) 0.003(3) 0.039(2) 0.002(2) C3 0.056(3) 0.046(3) 0.049(2) 0.010(2) 0.007(2) -0.006(2) C4 0.064(3) 0.042(2) 0.073(3) -0.007(2) 0.010(2) 0.001(2) C5 0.054(3) 0.046(3) 0.076(3) -0.012(2) 0.026(2) 0.002(2) C6 0.046(2) 0.042(2) 0.046(2) -0.0003(18) 0.0166(19) 0.0037(18) C7 0.088(3) 0.067(3) 0.077(3) 0.007(2) 0.008(3) -0.020(3) C8 0.041(2) 0.055(2) 0.043(2) 0.001(2) 0.0078(18) -0.002(2) C9 0.041(2) 0.082(3) 0.065(3) 0.015(3) 0.013(2) -0.009(2) C10 0.037(2) 0.098(4) 0.071(3) 0.001(3) 0.015(2) -0.013(2) C11 0.037(2) 0.078(3) 0.046(2) -0.005(2) 0.0054(19) 0.006(2) C12 0.043(3) 0.115(4) 0.063(3) -0.006(3) 0.008(2) 0.010(3) C13 0.058(3) 0.130(4) 0.053(3) 0.008(3) 0.003(2) 0.029(3) C14 0.067(3) 0.102(4) 0.060(3) 0.022(3) 0.010(2) 0.020(3) C15 0.050(2) 0.073(3) 0.056(3) 0.008(2) 0.012(2) 0.008(2) C16 0.039(2) 0.050(2) 0.045(2) -0.0056(19) 0.0116(18) 0.0032(19) C17 0.037(2) 0.044(2) 0.040(2) -0.0044(19) 0.0085(17) -0.0008(18) C18 0.041(2) 0.035(2) 0.045(2) -0.0004(17) 0.0096(17) 0.0002(17) C19 0.034(2) 0.043(2) 0.052(2) 0.0021(18) -0.0007(18) 0.0029(17) C20 0.035(2) 0.037(2) 0.048(2) -0.0092(18) 0.0318(17) 0.0026(17) C21 0.062(3) 0.131(5) 0.088(4) 0.038(4) 0.025(3) -0.018(3) C22 0.070(3) 0.099(4) 0.061(3) -0.029(3) 0.004(2) 0.039(3) C23 0.039(2) 0.060(2) 0.049(2) -0.003(2) 0.0108(17) -0.009(2) S1' 0.0563(7) 0.0779(9) 0.0491(6) 0.0036(6) 0.0113(5) -0.0020(7) S2' 0.0787(8) 0.0741(8) 0.0787(8) -0.0176(7) 0.0241(7) -0.0189(7) N1' 0.057(3) 0.063(3) 0.081(3) -0.006(2) -0.002(2) -0.015(2) O1' 0.0582(16) 0.0549(16) 0.0461(15) 0.0051(14) 0.0138(12) -0.0015(14) O2' 0.0652(18) 0.109(3) 0.0655(19) 0.0198(18) 0.0179(15) 0.0297(18) O3' 0.086(2) 0.088(2) 0.0641(19) -0.0086(17) 0.0179(16) -0.0294(19) O4' 0.077(2) 0.077(3) 0.150(3) 0.032(2) -0.030(2) -0.009(2) O5' 0.070(2) 0.093(3) 0.153(3) 0.019(2) -0.012(2) -0.045(2) C1' 0.076(3) 0.067(3) 0.075(3) 0.001(3) 0.030(3) 0.007(3) C2' 0.085(4) 0.078(4) 0.078(3) 0.011(3) 0.032(3) -0.012(3) C3' 0.065(3) 0.121(5) 0.045(2) 0.003(3) 0.021(2) -0.007(4) C4' 0.083(4) 0.099(4) 0.075(3) -0.002(3) 0.023(3) 0.032(3) C5' 0.083(3) 0.060(3) 0.080(3) 0.005(3) 0.023(3) 0.006(3) C6' 0.057(2) 0.045(2) 0.050(2) 0.003(2) 0.0115(18) 0.006(2) C7' 0.077(3) 0.196(6) 0.070(3) -0.010(4) 0.031(3) -0.008(4) C8' 0.042(2) 0.056(3) 0.044(2) 0.002(2) 0.0069(19) -0.011(2) C9' 0.047(3) 0.087(3) 0.044(2) 0.008(2) 0.009(2) -0.015(2) C10' 0.041(2) 0.104(4) 0.057(3) -0.004(3) 0.012(2) -0.006(3) C11' 0.043(2) 0.064(3) 0.045(2) -0.006(2) 0.0092(19) 0.001(2) C12' 0.048(2) 0.075(3) 0.063(3) -0.010(3) 0.010(2) 0.006(2) C13' 0.079(3) 0.062(3) 0.054(3) -0.015(2) -0.001(2) 0.023(3) C14' 0.074(3) 0.052(3) 0.060(3) -0.001(2) 0.013(2) 0.002(2) C15' 0.053(2) 0.052(3) 0.056(2) -0.002(2) 0.009(2) -0.002(2) C16' 0.045(2) 0.043(2) 0.047(2) -0.0058(19) 0.0092(19) -0.0038(19) C17' 0.039(2) 0.050(2) 0.044(2) -0.0058(19) 0.0070(18) -0.0076(19) C18' 0.042(2) 0.044(2) 0.058(2) 0.004(2) 0.0058(18) -0.0085(19) C19' 0.039(2) 0.048(2) 0.050(2) 0.0014(19) 0.0131(18) -0.0035(19) C20' 0.044(2) 0.055(3) 0.071(3) -0.002(2) 0.018(2) -0.009(2) C21' 0.062(3) 0.099(4) 0.073(3) 0.021(3) 0.030(3) 0.016(3) C22' 0.075(3) 0.084(4) 0.064(3) -0.008(3) 0.020(2) 0.017(3) C23' 0.046(2) 0.068(3) 0.061(2) -0.005(2) 0.0079(19) -0.005(2) _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 S1 O3 1.425(3) . ? S1 O2 1.427(3) . ? S1 O1 1.601(2) . ? S1 C6 1.746(4) . ? S2 C22 1.688(5) . ? S2 C19 1.694(4) . ? O1 C8 1.422(4) . ? O4 N1 1.200(4) . ? O5 N1 1.211(4) . ? N1 C23 1.489(5) . ? C1 C6 1.376(4) . ? C1 C2 1.386(5) . ? C1 H1 0.9300 . ? C2 C3 1.362(5) . ? C2 H2 0.9300 . ? C3 C4 1.378(5) . ? C3 C7 1.504(5) . ? C4 C5 1.380(5) . ? C4 H4 0.9300 . ? C5 C6 1.364(5) . ? C5 H5 0.9300 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 C17 1.375(5) . ? C8 C9 1.395(5) . ? C9 C10 1.357(5) . ? C9 H9 0.9300 . ? C10 C11 1.404(5) . ? C10 H10 0.9300 . ? C11 C16 1.415(5) . ? C11 C12 1.421(5) . ? C12 C13 1.357(6) . ? C12 H12 0.9300 . ? C13 C14 1.398(5) . ? C13 H13 0.9300 . ? C14 C15 1.363(5) . ? C14 H14 0.9300 . ? C15 C16 1.430(5) . ? C15 H15 0.9300 . ? C16 C17 1.428(5) . ? C17 C18 1.527(4) . ? C18 C19 1.512(5) . ? C18 C23 1.535(4) . ? C18 H18 0.9800 . ? C19 C20 1.436(5) . ? C20 C21 1.336(7) . ? C20 H20 0.9300 . ? C21 C22 1.333(6) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? S1' O2' 1.419(3) . ? S1' O3' 1.427(3) . ? S1' O1' 1.613(2) . ? S1' C6' 1.749(4) . ? S2' C22' 1.694(4) . ? S2' C19' 1.712(4) . ? N1' O5' 1.200(4) . ? N1' O4' 1.211(4) . ? N1' C23' 1.489(5) . ? O1' C8' 1.426(4) . ? C1' C2' 1.366(6) . ? C1' C6' 1.379(5) . ? C1' H1' 0.9300 . ? C2' C3' 1.351(6) . ? C2' H2' 0.9300 . ? C3' C4' 1.365(7) . ? C3' C7' 1.519(5) . ? C4' C5' 1.399(6) . ? C4' H4' 0.9300 . ? C5' C6' 1.362(5) . ? C5' H5' 0.9300 . ? C7' H7'1 0.9600 . ? C7' H7'2 0.9600 . ? C7' H7'3 0.9600 . ? C8' C17' 1.359(5) . ? C8' C9' 1.403(5) . ? C9' C10' 1.354(5) . ? C9' H9' 0.9300 . ? C10' C11' 1.403(5) . ? C10' H10' 0.9300 . ? C11' C12' 1.398(5) . ? C11' C16' 1.422(5) . ? C12' C13' 1.363(5) . ? C12' H12' 0.9300 . ? C13' C14' 1.394(5) . ? C13' H13' 0.9300 . ? C14' C15' 1.348(5) . ? C14' H14' 0.9300 . ? C15' C16' 1.414(5) . ? C15' H15' 0.9300 . ? C16' C17' 1.433(5) . ? C17' C18' 1.532(5) . ? C18' C19' 1.499(5) . ? C18' C23' 1.531(5) . ? C18' H18' 0.9800 . ? C19' C20' 1.370(5) . ? C20' C21' 1.403(6) . ? C20' H20' 0.9300 . ? C21' C22' 1.339(6) . ? C21' H21' 0.9300 . ? C22' H22' 0.9300 . ? C23' H23C 0.9700 . ? C23' H23D 0.9700 . ? 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 O3 S1 O2 120.64(17) . . ? O3 S1 O1 109.19(15) . . ? O2 S1 O1 102.30(14) . . ? O3 S1 C6 110.06(17) . . ? O2 S1 C6 109.33(17) . . ? O1 S1 C6 103.81(15) . . ? C22 S2 C19 92.2(2) . . ? C8 O1 S1 121.2(2) . . ? O4 N1 O5 122.9(4) . . ? O4 N1 C23 119.2(4) . . ? O5 N1 C23 117.8(4) . . ? C6 C1 C2 119.1(4) . . ? C6 C1 H1 120.5 . . ? C2 C1 H1 120.5 . . ? C3 C2 C1 121.2(4) . . ? C3 C2 H2 119.4 . . ? C1 C2 H2 119.4 . . ? C2 C3 C4 118.9(4) . . ? C2 C3 C7 121.4(4) . . ? C4 C3 C7 119.8(4) . . ? C3 C4 C5 120.6(4) . . ? C3 C4 H4 119.7 . . ? C5 C4 H4 119.7 . . ? C6 C5 C4 119.9(4) . . ? C6 C5 H5 120.1 . . ? C4 C5 H5 120.1 . . ? C5 C6 C1 120.3(4) . . ? C5 C6 S1 119.4(3) . . ? C1 C6 S1 120.2(3) . . ? C3 C7 H7A 109.5 . . ? C3 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C3 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C17 C8 C9 123.6(3) . . ? C17 C8 O1 117.7(3) . . ? C9 C8 O1 118.5(3) . . ? C10 C9 C8 118.9(4) . . ? C10 C9 H9 120.6 . . ? C8 C9 H9 120.6 . . ? C9 C10 C11 121.5(4) . . ? C9 C10 H10 119.3 . . ? C11 C10 H10 119.3 . . ? C10 C11 C16 118.9(4) . . ? C10 C11 C12 121.2(4) . . ? C16 C11 C12 119.8(4) . . ? C13 C12 C11 120.5(4) . . ? C13 C12 H12 119.7 . . ? C11 C12 H12 119.7 . . ? C12 C13 C14 121.1(4) . . ? C12 C13 H13 119.5 . . ? C14 C13 H13 119.5 . . ? C15 C14 C13 119.3(4) . . ? C15 C14 H14 120.3 . . ? C13 C14 H14 120.3 . . ? C14 C15 C16 122.4(4) . . ? C14 C15 H15 118.8 . . ? C16 C15 H15 118.8 . . ? C11 C16 C17 120.1(3) . . ? C11 C16 C15 116.8(3) . . ? C17 C16 C15 123.1(3) . . ? C8 C17 C16 117.1(3) . . ? C8 C17 C18 124.6(3) . . ? C16 C17 C18 118.2(3) . . ? C19 C18 C17 111.6(3) . . ? C19 C18 C23 110.6(3) . . ? C17 C18 C23 115.7(3) . . ? C19 C18 H18 106.1 . . ? C17 C18 H18 106.1 . . ? C23 C18 H18 106.1 . . ? C20 C19 C18 126.2(3) . . ? C20 C19 S2 110.5(3) . . ? C18 C19 S2 123.1(3) . . ? C21 C20 C19 109.0(4) . . ? C21 C20 H20 125.5 . . ? C19 C20 H20 125.5 . . ? C22 C21 C20 118.0(5) . . ? C22 C21 H21 121.0 . . ? C20 C21 H21 121.0 . . ? C21 C22 S2 110.2(4) . . ? C21 C22 H22 124.9 . . ? S2 C22 H22 124.9 . . ? N1 C23 C18 107.9(3) . . ? N1 C23 H23A 110.1 . . ? C18 C23 H23A 110.1 . . ? N1 C23 H23B 110.1 . . ? C18 C23 H23B 110.1 . . ? H23A C23 H23B 108.4 . . ? O2' S1' O3' 121.19(18) . . ? O2' S1' O1' 102.58(16) . . ? O3' S1' O1' 108.24(15) . . ? O2' S1' C6' 109.92(18) . . ? O3' S1' C6' 109.12(19) . . ? O1' S1' C6' 104.34(16) . . ? C22' S2' C19' 92.6(2) . . ? O5' N1' O4' 122.8(4) . . ? O5' N1' C23' 118.3(4) . . ? O4' N1' C23' 118.8(4) . . ? C8' O1' S1' 118.3(2) . . ? C2' C1' C6' 118.9(4) . . ? C2' C1' H1' 120.5 . . ? C6' C1' H1' 120.5 . . ? C3' C2' C1' 122.7(5) . . ? C3' C2' H2' 118.6 . . ? C1' C2' H2' 118.6 . . ? C2' C3' C4' 117.9(4) . . ? C2' C3' C7' 123.7(6) . . ? C4' C3' C7' 118.3(6) . . ? C3' C4' C5' 121.4(5) . . ? C3' C4' H4' 119.3 . . ? C5' C4' H4' 119.3 . . ? C6' C5' C4' 118.7(5) . . ? C6' C5' H5' 120.7 . . ? C4' C5' H5' 120.7 . . ? C5' C6' C1' 120.3(4) . . ? C5' C6' S1' 119.7(3) . . ? C1' C6' S1' 119.9(3) . . ? C3' C7' H7'1 109.5 . . ? C3' C7' H7'2 109.5 . . ? H7'1 C7' H7'2 109.5 . . ? C3' C7' H7'3 109.5 . . ? H7'1 C7' H7'3 109.5 . . ? H7'2 C7' H7'3 109.5 . . ? C17' C8' C9' 123.1(4) . . ? C17' C8' O1' 120.7(3) . . ? C9' C8' O1' 116.0(3) . . ? C10' C9' C8' 119.3(4) . . ? C10' C9' H9' 120.4 . . ? C8' C9' H9' 120.4 . . ? C9' C10' C11' 121.4(4) . . ? C9' C10' H10' 119.3 . . ? C11' C10' H10' 119.3 . . ? C12' C11' C10' 121.4(4) . . ? C12' C11' C16' 119.9(4) . . ? C10' C11' C16' 118.7(4) . . ? C13' C12' C11' 121.2(4) . . ? C13' C12' H12' 119.4 . . ? C11' C12' H12' 119.4 . . ? C12' C13' C14' 119.6(4) . . ? C12' C13' H13' 120.2 . . ? C14' C13' H13' 120.2 . . ? C15' C14' C13' 120.3(4) . . ? C15' C14' H14' 119.9 . . ? C13' C14' H14' 119.9 . . ? C14' C15' C16' 122.6(4) . . ? C14' C15' H15' 118.7 . . ? C16' C15' H15' 118.7 . . ? C15' C16' C11' 116.4(3) . . ? C15' C16' C17' 123.8(3) . . ? C11' C16' C17' 119.8(3) . . ? C8' C17' C16' 117.6(3) . . ? C8' C17' C18' 119.4(3) . . ? C16' C17' C18' 122.9(3) . . ? C19' C18' C23' 114.3(3) . . ? C19' C18' C17' 113.7(3) . . ? C23' C18' C17' 110.8(3) . . ? C19' C18' H18' 105.7 . . ? C23' C18' H18' 105.7 . . ? C17' C18' H18' 105.7 . . ? C20' C19' C18' 130.9(3) . . ? C20' C19' S2' 109.7(3) . . ? C18' C19' S2' 119.1(3) . . ? C19' C20' C21' 113.1(4) . . ? C19' C20' H20' 123.5 . . ? C21' C20' H20' 123.5 . . ? C22' C21' C20' 113.0(4) . . ? C22' C21' H21' 123.5 . . ? C20' C21' H21' 123.5 . . ? C21' C22' S2' 111.6(4) . . ? C21' C22' H22' 124.2 . . ? S2' C22' H22' 124.2 . . ? N1' C23' C18' 112.8(3) . . ? N1' C23' H23C 109.0 . . ? C18' C23' H23C 109.0 . . ? N1' C23' H23D 109.0 . . ? C18' C23' H23D 109.0 . . ? H23C C23' H23D 107.8 . . ? 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 O3 S1 O1 C8 -31.1(3) . . . . ? O2 S1 O1 C8 -160.0(3) . . . . ? C6 S1 O1 C8 86.3(3) . . . . ? C6 C1 C2 C3 -1.0(6) . . . . ? C1 C2 C3 C4 2.2(6) . . . . ? C1 C2 C3 C7 -176.7(4) . . . . ? C2 C3 C4 C5 -1.5(6) . . . . ? C7 C3 C4 C5 177.5(3) . . . . ? C3 C4 C5 C6 -0.5(6) . . . . ? C4 C5 C6 C1 1.8(6) . . . . ? C4 C5 C6 S1 -178.4(3) . . . . ? C2 C1 C6 C5 -1.0(6) . . . . ? C2 C1 C6 S1 179.2(3) . . . . ? O3 S1 C6 C5 172.8(3) . . . . ? O2 S1 C6 C5 -52.5(4) . . . . ? O1 S1 C6 C5 56.1(3) . . . . ? O3 S1 C6 C1 -7.4(4) . . . . ? O2 S1 C6 C1 127.3(3) . . . . ? O1 S1 C6 C1 -124.1(3) . . . . ? S1 O1 C8 C17 117.4(3) . . . . ? S1 O1 C8 C9 -67.7(4) . . . . ? C17 C8 C9 C10 -1.0(6) . . . . ? O1 C8 C9 C10 -175.5(3) . . . . ? C8 C9 C10 C11 1.7(7) . . . . ? C9 C10 C11 C16 -0.4(6) . . . . ? C9 C10 C11 C12 179.4(4) . . . . ? C10 C11 C12 C13 -179.3(4) . . . . ? C16 C11 C12 C13 0.5(6) . . . . ? C11 C12 C13 C14 0.9(7) . . . . ? C12 C13 C14 C15 -0.9(7) . . . . ? C13 C14 C15 C16 -0.5(7) . . . . ? C10 C11 C16 C17 -1.6(5) . . . . ? C12 C11 C16 C17 178.6(3) . . . . ? C10 C11 C16 C15 178.0(4) . . . . ? C12 C11 C16 C15 -1.8(5) . . . . ? C14 C15 C16 C11 1.8(6) . . . . ? C14 C15 C16 C17 -178.6(4) . . . . ? C9 C8 C17 C16 -1.0(5) . . . . ? O1 C8 C17 C16 173.5(3) . . . . ? C9 C8 C17 C18 -176.4(4) . . . . ? O1 C8 C17 C18 -1.8(5) . . . . ? C11 C16 C17 C8 2.3(5) . . . . ? C15 C16 C17 C8 -177.3(3) . . . . ? C11 C16 C17 C18 178.0(3) . . . . ? C15 C16 C17 C18 -1.6(5) . . . . ? C8 C17 C18 C19 91.7(4) . . . . ? C16 C17 C18 C19 -83.6(4) . . . . ? C8 C17 C18 C23 -35.8(5) . . . . ? C16 C17 C18 C23 148.9(3) . . . . ? C17 C18 C19 C20 138.5(3) . . . . ? C23 C18 C19 C20 -91.2(4) . . . . ? C17 C18 C19 S2 -46.0(4) . . . . ? C23 C18 C19 S2 84.3(4) . . . . ? C22 S2 C19 C20 0.9(3) . . . . ? C22 S2 C19 C18 -175.2(3) . . . . ? C18 C19 C20 C21 174.6(4) . . . . ? S2 C19 C20 C21 -1.3(4) . . . . ? C19 C20 C21 C22 1.3(6) . . . . ? C20 C21 C22 S2 -0.6(6) . . . . ? C19 S2 C22 C21 -0.2(4) . . . . ? O4 N1 C23 C18 63.8(5) . . . . ? O5 N1 C23 C18 -115.0(4) . . . . ? C19 C18 C23 N1 68.6(4) . . . . ? C17 C18 C23 N1 -163.4(3) . . . . ? O2' S1' O1' C8' 174.2(2) . . . . ? O3' S1' O1' C8' 45.0(3) . . . . ? C6' S1' O1' C8' -71.1(3) . . . . ? C6' C1' C2' C3' 0.5(7) . . . . ? C1' C2' C3' C4' -0.8(7) . . . . ? C1' C2' C3' C7' -179.9(4) . . . . ? C2' C3' C4' C5' 0.9(7) . . . . ? C7' C3' C4' C5' -179.9(4) . . . . ? C3' C4' C5' C6' -0.8(7) . . . . ? C4' C5' C6' C1' 0.5(6) . . . . ? C4' C5' C6' S1' -178.4(3) . . . . ? C2' C1' C6' C5' -0.3(6) . . . . ? C2' C1' C6' S1' 178.6(3) . . . . ? O2' S1' C6' C5' -146.2(3) . . . . ? O3' S1' C6' C5' -11.1(4) . . . . ? O1' S1' C6' C5' 104.4(3) . . . . ? O2' S1' C6' C1' 34.9(4) . . . . ? O3' S1' C6' C1' 170.0(3) . . . . ? O1' S1' C6' C1' -74.5(4) . . . . ? S1' O1' C8' C17' -96.0(3) . . . . ? S1' O1' C8' C9' 88.6(3) . . . . ? C17' C8' C9' C10' 3.1(6) . . . . ? O1' C8' C9' C10' 178.3(3) . . . . ? C8' C9' C10' C11' -0.8(6) . . . . ? C9' C10' C11' C12' 179.5(4) . . . . ? C9' C10' C11' C16' -2.1(6) . . . . ? C10' C11' C12' C13' 177.9(4) . . . . ? C16' C11' C12' C13' -0.5(6) . . . . ? C11' C12' C13' C14' 0.1(6) . . . . ? C12' C13' C14' C15' -0.8(6) . . . . ? C13' C14' C15' C16' 1.9(6) . . . . ? C14' C15' C16' C11' -2.3(5) . . . . ? C14' C15' C16' C17' 177.9(3) . . . . ? C12' C11' C16' C15' 1.5(5) . . . . ? C10' C11' C16' C15' -176.9(3) . . . . ? C12' C11' C16' C17' -178.6(3) . . . . ? C10' C11' C16' C17' 2.9(5) . . . . ? C9' C8' C17' C16' -2.2(5) . . . . ? O1' C8' C17' C16' -177.2(3) . . . . ? C9' C8' C17' C18' 177.1(3) . . . . ? O1' C8' C17' C18' 2.1(5) . . . . ? C15' C16' C17' C8' 179.0(3) . . . . ? C11' C16' C17' C8' -0.9(5) . . . . ? C15' C16' C17' C18' -0.2(5) . . . . ? C11' C16' C17' C18' 179.9(3) . . . . ? C8' C17' C18' C19' -112.0(4) . . . . ? C16' C17' C18' C19' 67.3(4) . . . . ? C8' C17' C18' C23' 117.7(4) . . . . ? C16' C17' C18' C23' -63.1(4) . . . . ? C23' C18' C19' C20' -4.9(6) . . . . ? C17' C18' C19' C20' -133.5(4) . . . . ? C23' C18' C19' S2' -177.7(2) . . . . ? C17' C18' C19' S2' 53.8(4) . . . . ? C22' S2' C19' C20' 0.7(3) . . . . ? C22' S2' C19' C18' 174.9(3) . . . . ? C18' C19' C20' C21' -173.9(4) . . . . ? S2' C19' C20' C21' -0.6(4) . . . . ? C19' C20' C21' C22' 0.2(6) . . . . ? C20' C21' C22' S2' 0.4(5) . . . . ? C19' S2' C22' C21' -0.6(4) . . . . ? O5' N1' C23' C18' -139.9(4) . . . . ? O4' N1' C23' C18' 42.8(5) . . . . ? C19' C18' C23' N1' 66.9(4) . . . . ? C17' C18' C23' N1' -163.0(3) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.230 _refine_diff_density_min -0.346 _refine_diff_density_rms 0.037 # Attachment 'racemic_5aa.cif' data_racemic5aa _database_code_depnum_ccdc_archive 'CCDC 642669' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C37 H31.50 N O4' _chemical_formula_weight 554.13 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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 30.038(4) _cell_length_b 9.530(1) _cell_length_c 24.662(4) _cell_angle_alpha 90.00 _cell_angle_beta 124.57(1) _cell_angle_gamma 90.00 _cell_volume 5813.3(14) _cell_formula_units_Z 8 _cell_measurement_temperature 289(2) _cell_measurement_reflns_used 36 _cell_measurement_theta_min 3.33 _cell_measurement_theta_max 14.33 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.266 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2340 _exptl_absorpt_coefficient_mu 0.082 _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 289(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Siemens P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 3.54 _diffrn_reflns_number 6867 _diffrn_reflns_av_R_equivalents 0.0175 _diffrn_reflns_av_sigmaI/netI 0.0992 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 36 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.65 _diffrn_reflns_theta_max 25.50 _reflns_number_total 5409 _reflns_number_gt 2235 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens 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^)+(0.0086P)^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 constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00166(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5409 _refine_ls_number_parameters 413 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1273 _refine_ls_R_factor_gt 0.0439 _refine_ls_wR_factor_ref 0.0599 _refine_ls_wR_factor_gt 0.0515 _refine_ls_goodness_of_fit_ref 0.864 _refine_ls_restrained_S_all 0.865 _refine_ls_shift/su_max 0.001 _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 0.44460(6) 0.59394(17) 0.65814(7) 0.0530(5) Uani 1 1 d . . . O2 O 0.50776(6) 0.30204(17) 0.67257(7) 0.0543(5) Uani 1 1 d . . . O3 O 0.52289(13) 0.6458(3) 0.63370(14) 0.0506(9) Uani 0.50 1 d P A 1 H3O H 0.5281 0.6638 0.6052 0.061 Uiso 1 1 calc R A 1 O3' O 0.49490(16) 0.4585(3) 0.56928(16) 0.0581(10) Uani 0.50 1 d P A 2 H3O' H 0.4955 0.5192 0.5462 0.070 Uiso 0.50 1 calc PR A 2 N1 N 0.49818(7) 0.5196(2) 0.62100(9) 0.0462(5) Uani 1 1 d . . . C1 C 0.42644(9) 0.7315(3) 0.64263(12) 0.0451(6) Uani 1 1 d . . . C2 C 0.42818(9) 0.8214(3) 0.68850(11) 0.0552(7) Uani 1 1 d . . . H2 H 0.4419 0.7920 0.7312 0.066 Uiso 1 1 calc R . . C3 C 0.40886(9) 0.9545(3) 0.66780(12) 0.0572(7) Uani 1 1 d . . . H3 H 0.4093 1.0171 0.6970 0.069 Uiso 1 1 calc R . . C4 C 0.38822(9) 0.9989(3) 0.60288(11) 0.0472(7) Uani 1 1 d . . . C5 C 0.36995(10) 1.1385(3) 0.58234(13) 0.0615(8) Uani 1 1 d . . . H5 H 0.3707 1.2013 0.6117 0.074 Uiso 1 1 calc R . . C6 C 0.35146(10) 1.1818(3) 0.52090(13) 0.0702(9) Uani 1 1 d . . . H6 H 0.3392 1.2734 0.5081 0.084 Uiso 1 1 calc R . . C7 C 0.35068(10) 1.0896(3) 0.47680(12) 0.0654(8) Uani 1 1 d . . . H7 H 0.3384 1.1207 0.4347 0.079 Uiso 1 1 calc R . . C8 C 0.36767(9) 0.9543(3) 0.49415(11) 0.0525(7) Uani 1 1 d . . . H8 H 0.3663 0.8939 0.4636 0.063 Uiso 1 1 calc R . . C9 C 0.38721(8) 0.9050(3) 0.55775(11) 0.0402(6) Uani 1 1 d . . . C10 C 0.40674(8) 0.7677(2) 0.57979(11) 0.0404(6) Uani 1 1 d . A . C11 C 0.41061(8) 0.6437(2) 0.54447(10) 0.0422(6) Uani 1 1 d . . . H11 H 0.4326 0.6697 0.5282 0.051 Uiso 1 1 calc R A . C12 C 0.44298(8) 0.5378(2) 0.60283(10) 0.0457(6) Uani 1 1 d . A . H12 H 0.4244 0.4469 0.5903 0.055 Uiso 1 1 calc R . . C13 C 0.35693(10) 0.5847(2) 0.48800(11) 0.0478(7) Uani 1 1 d . A . C14 C 0.31208(10) 0.5834(3) 0.48971(12) 0.0648(8) Uani 1 1 d . . . H14 H 0.3142 0.6227 0.5256 0.078 Uiso 1 1 calc R A . C15 C 0.26346(11) 0.5246(3) 0.43880(15) 0.0887(11) Uani 1 1 d . A . H15 H 0.2334 0.5238 0.4406 0.106 Uiso 1 1 calc R . . C16 C 0.26089(14) 0.4676(3) 0.38576(16) 0.1022(15) Uani 1 1 d . . . H16 H 0.2287 0.4284 0.3512 0.123 Uiso 1 1 calc R A . C17 C 0.30481(14) 0.4685(3) 0.38361(15) 0.1011(12) Uani 1 1 d . A . H17 H 0.3027 0.4295 0.3476 0.121 Uiso 1 1 calc R . . C18 C 0.35316(11) 0.5270(3) 0.43459(12) 0.0753(9) Uani 1 1 d . . . H18 H 0.3831 0.5271 0.4325 0.090 Uiso 1 1 calc R A . C19 C 0.54175(9) 0.2034(3) 0.67358(11) 0.0452(7) Uani 1 1 d . . . C20 C 0.52923(9) 0.0605(3) 0.66331(11) 0.0550(7) Uani 1 1 d . . . H20 H 0.4969 0.0265 0.6551 0.066 Uiso 1 1 calc R . . C21 C 0.56629(11) -0.0272(3) 0.66574(11) 0.0597(7) Uani 1 1 d . . . H21 H 0.5589 -0.1228 0.6590 0.072 Uiso 1 1 calc R . . C22 C 0.61541(10) 0.0232(3) 0.67818(11) 0.0545(7) Uani 1 1 d . . . C23 C 0.65386(12) -0.0675(3) 0.68074(12) 0.0744(9) Uani 1 1 d . . . H23 H 0.6470 -0.1633 0.6744 0.089 Uiso 1 1 calc R . . C24 C 0.70056(12) -0.0163(4) 0.69237(13) 0.0835(11) Uani 1 1 d . . . H24 H 0.7255 -0.0775 0.6942 0.100 Uiso 1 1 calc R . . C25 C 0.71178(11) 0.1276(4) 0.70164(12) 0.0786(10) Uani 1 1 d . . . H25 H 0.7439 0.1612 0.7091 0.094 Uiso 1 1 calc R . . C26 C 0.67609(9) 0.2187(3) 0.69980(11) 0.0600(8) Uani 1 1 d . . . H26 H 0.6841 0.3140 0.7065 0.072 Uiso 1 1 calc R . . C27 C 0.62680(9) 0.1692(3) 0.68779(10) 0.0474(7) Uani 1 1 d . . . C28 C 0.58841(9) 0.2580(3) 0.68586(10) 0.0421(6) Uani 1 1 d . A . C29 C 0.58948(8) 0.4137(2) 0.69609(10) 0.0461(7) Uani 1 1 d . . . H29 H 0.5918 0.4619 0.6627 0.055 Uiso 1 1 calc R A . C30 C 0.53231(8) 0.4384(3) 0.68120(10) 0.0469(7) Uani 1 1 d . A . H30 H 0.5356 0.4874 0.7183 0.056 Uiso 1 1 calc R . . C31 C 0.63455(9) 0.4664(3) 0.76398(12) 0.0476(7) Uani 1 1 d . A . C32 C 0.66351(10) 0.3794(3) 0.81721(12) 0.0663(8) Uani 1 1 d . . . H32 H 0.6555 0.2841 0.8124 0.080 Uiso 1 1 calc R A . C33 C 0.70462(11) 0.4312(3) 0.87836(14) 0.0864(10) Uani 1 1 d . A . H33 H 0.7240 0.3705 0.9140 0.104 Uiso 1 1 calc R . . C34 C 0.71667(12) 0.5705(4) 0.88631(16) 0.0884(12) Uani 1 1 d . . . H34 H 0.7446 0.6050 0.9271 0.106 Uiso 1 1 calc R A . C35 C 0.68746(12) 0.6593(3) 0.83398(16) 0.0859(11) Uani 1 1 d . A . H35 H 0.6948 0.7550 0.8394 0.103 Uiso 1 1 calc R . . C36 C 0.64695(10) 0.6070(3) 0.77278(14) 0.0719(9) Uani 1 1 d . . . H36 H 0.6279 0.6680 0.7372 0.086 Uiso 1 1 calc R A . O4 O 0.4908(2) 0.3720(4) 0.5068(2) 0.0866(14) Uani 0.50 1 d PD B 1 H4O H 0.4916 0.4048 0.5382 0.095 Uiso 0.50 1 calc PR B 1 C37 C 0.4749(4) 0.2231(5) 0.4985(6) 0.110(4) Uani 0.50 1 d PD B 1 H37A H 0.4631 0.1926 0.4552 0.121 Uiso 0.50 1 calc PR B 1 H37B H 0.4459 0.2120 0.5040 0.121 Uiso 0.50 1 calc PR B 1 H37C H 0.5053 0.1677 0.5308 0.121 Uiso 0.50 1 calc PR B 1 O4' O 0.4636(3) 0.2843(6) 0.4635(3) 0.099(2) Uani 0.50 1 d PD C 2 H4O' H 0.4536 0.3202 0.4851 0.109 Uiso 0.50 1 calc PR C 2 C37' C 0.4957(4) 0.1581(7) 0.4976(5) 0.112(4) Uani 0.50 1 d PD C 2 H37D H 0.5137 0.1273 0.4777 0.124 Uiso 0.50 1 calc PR C 2 H37E H 0.4723 0.0850 0.4943 0.124 Uiso 0.50 1 calc PR C 2 H37F H 0.5221 0.1796 0.5432 0.124 Uiso 0.50 1 calc PR C 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0556(11) 0.0633(12) 0.0440(10) 0.0146(10) 0.0306(9) 0.0157(10) O2 0.0403(10) 0.0487(11) 0.0732(12) 0.0173(10) 0.0318(9) 0.0057(9) O3 0.054(2) 0.047(2) 0.055(2) 0.0092(18) 0.0333(19) -0.0029(18) O3' 0.067(2) 0.054(2) 0.056(3) 0.006(2) 0.037(2) 0.013(2) N1 0.0426(13) 0.0471(15) 0.0457(13) 0.0060(12) 0.0233(11) 0.0025(11) C1 0.0357(14) 0.0521(18) 0.0461(16) 0.0067(15) 0.0224(13) 0.0068(14) C2 0.0492(16) 0.078(2) 0.0399(15) 0.0018(16) 0.0261(14) 0.0036(16) C3 0.0501(17) 0.065(2) 0.0531(17) -0.0079(16) 0.0269(15) 0.0019(16) C4 0.0386(15) 0.0506(19) 0.0448(16) -0.0030(15) 0.0190(14) -0.0004(14) C5 0.0607(19) 0.0490(19) 0.0661(19) -0.0115(16) 0.0307(17) 0.0018(15) C6 0.076(2) 0.0462(19) 0.069(2) 0.0022(17) 0.0288(18) 0.0093(17) C7 0.074(2) 0.051(2) 0.0510(18) 0.0101(16) 0.0234(16) 0.0066(17) C8 0.0531(17) 0.0462(19) 0.0451(16) 0.0013(14) 0.0200(14) 0.0020(14) C9 0.0276(13) 0.0456(16) 0.0365(14) 0.0009(14) 0.0117(12) -0.0029(12) C10 0.0330(13) 0.0460(17) 0.0366(15) -0.0004(14) 0.0165(12) 0.0009(13) C11 0.0388(14) 0.0457(16) 0.0403(14) 0.0094(13) 0.0213(12) 0.0039(13) C12 0.0359(14) 0.0506(17) 0.0459(15) 0.0097(14) 0.0205(13) 0.0061(13) C13 0.0489(17) 0.0408(17) 0.0405(15) 0.0054(13) 0.0174(14) 0.0044(14) C14 0.0498(17) 0.059(2) 0.0656(19) 0.0004(16) 0.0207(16) -0.0044(16) C15 0.052(2) 0.073(2) 0.099(2) 0.005(2) 0.018(2) -0.0123(18) C16 0.090(3) 0.060(2) 0.074(2) 0.006(2) -0.003(2) -0.016(2) C17 0.127(3) 0.075(2) 0.049(2) -0.0084(19) 0.019(3) -0.007(3) C18 0.080(2) 0.081(2) 0.0471(17) -0.0063(18) 0.0260(17) -0.0014(19) C19 0.0377(16) 0.0488(18) 0.0422(15) 0.0090(13) 0.0186(13) 0.0077(14) C20 0.0454(16) 0.057(2) 0.0544(17) 0.0099(15) 0.0232(14) -0.0050(15) C21 0.071(2) 0.0485(19) 0.0544(17) 0.0046(15) 0.0329(16) 0.0003(17) C22 0.0546(18) 0.061(2) 0.0426(16) 0.0091(15) 0.0243(15) 0.0149(17) C23 0.087(2) 0.078(2) 0.0593(19) 0.0088(17) 0.042(2) 0.025(2) C24 0.080(2) 0.108(3) 0.064(2) 0.012(2) 0.041(2) 0.044(2) C25 0.0509(19) 0.126(3) 0.062(2) 0.005(2) 0.0338(17) 0.018(2) C26 0.0437(16) 0.080(2) 0.0551(17) 0.0049(16) 0.0270(14) 0.0092(16) C27 0.0392(16) 0.060(2) 0.0378(15) 0.0069(14) 0.0189(13) 0.0085(15) C28 0.0341(14) 0.0505(18) 0.0363(14) 0.0042(13) 0.0167(12) 0.0019(14) C29 0.0378(15) 0.0531(18) 0.0481(16) 0.0044(13) 0.0247(13) 0.0002(13) C30 0.0373(15) 0.0547(19) 0.0402(15) 0.0086(14) 0.0169(13) 0.0049(14) C31 0.0385(16) 0.0493(17) 0.0560(17) -0.0045(15) 0.0274(14) -0.0038(14) C32 0.0580(19) 0.065(2) 0.0552(18) 0.0003(17) 0.0199(16) -0.0106(16) C33 0.066(2) 0.110(3) 0.054(2) -0.007(2) 0.0168(18) -0.008(2) C34 0.050(2) 0.125(4) 0.087(3) -0.048(3) 0.037(2) -0.022(2) C35 0.065(2) 0.079(3) 0.121(3) -0.039(2) 0.056(2) -0.022(2) C36 0.059(2) 0.060(2) 0.088(2) -0.0074(19) 0.0364(18) -0.0063(17) O4 0.132(4) 0.074(3) 0.083(4) -0.012(3) 0.079(4) -0.015(3) C37 0.099(9) 0.092(9) 0.099(8) 0.016(7) 0.032(7) 0.017(7) O4' 0.164(6) 0.069(4) 0.093(4) -0.002(3) 0.091(5) -0.007(4) C37' 0.112(8) 0.148(9) 0.076(5) 0.027(7) 0.052(5) 0.021(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.387(2) . ? O1 C12 1.440(2) . ? O2 C19 1.377(2) . ? O2 C30 1.449(2) . ? O3 N1 1.354(3) . ? O3 H3O 0.8200 . ? O3' N1 1.354(3) . ? O3' H3O' 0.8200 . ? N1 C30 1.458(2) . ? N1 C12 1.462(2) . ? C1 C10 1.353(3) . ? C1 C2 1.396(3) . ? C2 C3 1.368(3) . ? C2 H2 0.9300 . ? C3 C4 1.414(3) . ? C3 H3 0.9300 . ? C4 C9 1.415(3) . ? C4 C5 1.419(3) . ? C5 C6 1.349(3) . ? C5 H5 0.9300 . ? C6 C7 1.388(3) . ? C6 H6 0.9300 . ? C7 C8 1.364(3) . ? C7 H7 0.9300 . ? C8 C9 1.407(3) . ? C8 H8 0.9300 . ? C9 C10 1.411(3) . ? C10 C11 1.511(3) . ? C11 C13 1.519(3) . ? C11 C12 1.565(2) . ? C11 H11 0.9800 . ? C12 H12 0.9800 . ? C13 C18 1.371(3) . ? C13 C14 1.372(3) . ? C14 C15 1.394(3) . ? C14 H14 0.9300 . ? C15 C16 1.377(4) . ? C15 H15 0.9300 . ? C16 C17 1.350(4) . ? C16 H16 0.9300 . ? C17 C18 1.389(3) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? C19 C28 1.359(3) . ? C19 C20 1.397(3) . ? C20 C21 1.366(3) . ? C20 H20 0.9300 . ? C21 C22 1.410(3) . ? C21 H21 0.9300 . ? C22 C23 1.415(3) . ? C22 C27 1.420(3) . ? C23 C24 1.354(3) . ? C23 H23 0.9300 . ? C24 C25 1.400(4) . ? C24 H24 0.9300 . ? C25 C26 1.360(3) . ? C25 H25 0.9300 . ? C26 C27 1.416(3) . ? C26 H26 0.9300 . ? C27 C28 1.409(3) . ? C28 C29 1.502(3) . ? C29 C31 1.522(3) . ? C29 C30 1.557(3) . ? C29 H29 0.9800 . ? C30 H30 0.9800 . ? C31 C32 1.368(3) . ? C31 C36 1.375(3) . ? C32 C33 1.389(3) . ? C32 H32 0.9300 . ? C33 C34 1.360(4) . ? C33 H33 0.9300 . ? C34 C35 1.366(4) . ? C34 H34 0.9300 . ? C35 C36 1.387(3) . ? C35 H35 0.9300 . ? C36 H36 0.9300 . ? O4 C37 1.474(3) . ? O4 H4O 0.8200 . ? C37 H37A 0.9600 . ? C37 H37B 0.9600 . ? C37 H37C 0.9600 . ? O4' C37' 1.471(3) . ? O4' H4O' 0.8200 . ? C37' H37D 0.9600 . ? C37' H37E 0.9600 . ? C37' H37F 0.9600 . ? 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 C1 O1 C12 107.04(18) . . ? C19 O2 C30 107.41(17) . . ? N1 O3 H3O 109.5 . . ? N1 O3' H3O' 109.5 . . ? O3 N1 O3' 109.7(2) . . ? O3 N1 C30 105.0(2) . . ? O3' N1 C30 111.4(2) . . ? O3 N1 C12 110.1(2) . . ? O3' N1 C12 107.4(2) . . ? C30 N1 C12 113.27(18) . . ? C10 C1 O1 113.9(2) . . ? C10 C1 C2 124.2(2) . . ? O1 C1 C2 121.9(2) . . ? C3 C2 C1 117.0(2) . . ? C3 C2 H2 121.5 . . ? C1 C2 H2 121.5 . . ? C2 C3 C4 121.4(2) . . ? C2 C3 H3 119.3 . . ? C4 C3 H3 119.3 . . ? C3 C4 C9 120.1(2) . . ? C3 C4 C5 121.1(2) . . ? C9 C4 C5 118.7(2) . . ? C6 C5 C4 121.1(3) . . ? C6 C5 H5 119.4 . . ? C4 C5 H5 119.4 . . ? C5 C6 C7 120.0(3) . . ? C5 C6 H6 120.0 . . ? C7 C6 H6 120.0 . . ? C8 C7 C6 121.1(2) . . ? C8 C7 H7 119.5 . . ? C6 C7 H7 119.5 . . ? C7 C8 C9 120.7(2) . . ? C7 C8 H8 119.7 . . ? C9 C8 H8 119.7 . . ? C8 C9 C10 123.9(2) . . ? C8 C9 C4 118.4(2) . . ? C10 C9 C4 117.7(2) . . ? C1 C10 C9 119.6(2) . . ? C1 C10 C11 109.5(2) . . ? C9 C10 C11 130.9(2) . . ? C10 C11 C13 115.40(19) . . ? C10 C11 C12 100.67(17) . . ? C13 C11 C12 112.77(19) . . ? C10 C11 H11 109.2 . . ? C13 C11 H11 109.2 . . ? C12 C11 H11 109.2 . . ? O1 C12 N1 109.32(18) . . ? O1 C12 C11 107.52(18) . . ? N1 C12 C11 111.31(18) . . ? O1 C12 H12 109.5 . . ? N1 C12 H12 109.5 . . ? C11 C12 H12 109.5 . . ? C18 C13 C14 118.6(2) . . ? C18 C13 C11 119.7(2) . . ? C14 C13 C11 121.7(2) . . ? C13 C14 C15 121.4(3) . . ? C13 C14 H14 119.3 . . ? C15 C14 H14 119.3 . . ? C16 C15 C14 118.7(3) . . ? C16 C15 H15 120.7 . . ? C14 C15 H15 120.7 . . ? C17 C16 C15 120.4(4) . . ? C17 C16 H16 119.8 . . ? C15 C16 H16 119.8 . . ? C16 C17 C18 120.7(4) . . ? C16 C17 H17 119.7 . . ? C18 C17 H17 119.7 . . ? C13 C18 C17 120.3(3) . . ? C13 C18 H18 119.9 . . ? C17 C18 H18 119.9 . . ? C28 C19 O2 113.8(2) . . ? C28 C19 C20 123.4(2) . . ? O2 C19 C20 122.8(2) . . ? C21 C20 C19 117.4(2) . . ? C21 C20 H20 121.3 . . ? C19 C20 H20 121.3 . . ? C20 C21 C22 121.8(3) . . ? C20 C21 H21 119.1 . . ? C22 C21 H21 119.1 . . ? C21 C22 C23 121.9(3) . . ? C21 C22 C27 119.6(2) . . ? C23 C22 C27 118.6(3) . . ? C24 C23 C22 120.7(3) . . ? C24 C23 H23 119.6 . . ? C22 C23 H23 119.6 . . ? C23 C24 C25 120.8(3) . . ? C23 C24 H24 119.6 . . ? C25 C24 H24 119.6 . . ? C26 C25 C24 120.5(3) . . ? C26 C25 H25 119.7 . . ? C24 C25 H25 119.7 . . ? C25 C26 C27 120.4(3) . . ? C25 C26 H26 119.8 . . ? C27 C26 H26 119.8 . . ? C28 C27 C26 123.1(3) . . ? C28 C27 C22 117.9(2) . . ? C26 C27 C22 119.0(2) . . ? C19 C28 C27 119.9(2) . . ? C19 C28 C29 109.7(2) . . ? C27 C28 C29 130.4(2) . . ? C28 C29 C31 115.6(2) . . ? C28 C29 C30 101.20(19) . . ? C31 C29 C30 112.53(19) . . ? C28 C29 H29 109.1 . . ? C31 C29 H29 109.1 . . ? C30 C29 H29 109.1 . . ? O2 C30 N1 108.72(18) . . ? O2 C30 C29 107.47(18) . . ? N1 C30 C29 111.38(18) . . ? O2 C30 H30 109.7 . . ? N1 C30 H30 109.7 . . ? C29 C30 H30 109.7 . . ? C32 C31 C36 118.1(2) . . ? C32 C31 C29 122.7(2) . . ? C36 C31 C29 119.2(3) . . ? C31 C32 C33 121.0(3) . . ? C31 C32 H32 119.5 . . ? C33 C32 H32 119.5 . . ? C34 C33 C32 120.2(3) . . ? C34 C33 H33 119.9 . . ? C32 C33 H33 119.9 . . ? C33 C34 C35 119.5(3) . . ? C33 C34 H34 120.3 . . ? C35 C34 H34 120.3 . . ? C34 C35 C36 120.2(3) . . ? C34 C35 H35 119.9 . . ? C36 C35 H35 119.9 . . ? C31 C36 C35 120.9(3) . . ? C31 C36 H36 119.5 . . ? C35 C36 H36 119.5 . . ? C37' O4' H4O' 109.5 . . ? O4' C37' H37D 109.5 . . ? O4' C37' H37E 109.5 . . ? H37D C37' H37E 109.5 . . ? O4' C37' H37F 109.5 . . ? H37D C37' H37F 109.5 . . ? H37E C37' H37F 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 C12 O1 C1 C10 7.6(3) . . . . ? C12 O1 C1 C2 -173.2(2) . . . . ? C10 C1 C2 C3 -0.4(4) . . . . ? O1 C1 C2 C3 -179.5(2) . . . . ? C1 C2 C3 C4 -0.2(4) . . . . ? C2 C3 C4 C9 0.0(4) . . . . ? C2 C3 C4 C5 -177.8(2) . . . . ? C3 C4 C5 C6 178.4(2) . . . . ? C9 C4 C5 C6 0.5(4) . . . . ? C4 C5 C6 C7 -0.8(4) . . . . ? C5 C6 C7 C8 0.9(4) . . . . ? C6 C7 C8 C9 -0.9(4) . . . . ? C7 C8 C9 C10 -178.3(2) . . . . ? C7 C8 C9 C4 0.7(3) . . . . ? C3 C4 C9 C8 -178.4(2) . . . . ? C5 C4 C9 C8 -0.5(3) . . . . ? C3 C4 C9 C10 0.7(3) . . . . ? C5 C4 C9 C10 178.6(2) . . . . ? O1 C1 C10 C9 -179.67(19) . . . . ? C2 C1 C10 C9 1.2(4) . . . . ? O1 C1 C10 C11 0.0(3) . . . . ? C2 C1 C10 C11 -179.2(2) . . . . ? C8 C9 C10 C1 177.7(2) . . . . ? C4 C9 C10 C1 -1.2(3) . . . . ? C8 C9 C10 C11 -1.8(4) . . . . ? C4 C9 C10 C11 179.2(2) . . . . ? C1 C10 C11 C13 115.0(2) . . . . ? C9 C10 C11 C13 -65.4(3) . . . . ? C1 C10 C11 C12 -6.7(2) . . . . ? C9 C10 C11 C12 172.9(2) . . . . ? C1 O1 C12 N1 109.4(2) . . . . ? C1 O1 C12 C11 -11.6(2) . . . . ? O3 N1 C12 O1 -64.5(3) . . . . ? O3' N1 C12 O1 176.2(2) . . . . ? C30 N1 C12 O1 52.8(3) . . . . ? O3 N1 C12 C11 54.2(3) . . . . ? O3' N1 C12 C11 -65.2(3) . . . . ? C30 N1 C12 C11 171.41(19) . . . . ? C10 C11 C12 O1 11.0(2) . . . . ? C13 C11 C12 O1 -112.5(2) . . . . ? C10 C11 C12 N1 -108.7(2) . . . . ? C13 C11 C12 N1 127.7(2) . . . . ? C10 C11 C13 C18 147.7(2) . . . . ? C12 C11 C13 C18 -97.4(3) . . . . ? C10 C11 C13 C14 -34.4(3) . . . . ? C12 C11 C13 C14 80.5(3) . . . . ? C18 C13 C14 C15 0.3(4) . . . . ? C11 C13 C14 C15 -177.6(2) . . . . ? C13 C14 C15 C16 -0.4(4) . . . . ? C14 C15 C16 C17 0.3(5) . . . . ? C15 C16 C17 C18 -0.2(6) . . . . ? C14 C13 C18 C17 -0.1(4) . . . . ? C11 C13 C18 C17 177.9(2) . . . . ? C16 C17 C18 C13 0.1(5) . . . . ? C30 O2 C19 C28 3.6(3) . . . . ? C30 O2 C19 C20 -176.8(2) . . . . ? C28 C19 C20 C21 -0.2(4) . . . . ? O2 C19 C20 C21 -179.8(2) . . . . ? C19 C20 C21 C22 0.1(4) . . . . ? C20 C21 C22 C23 180.0(2) . . . . ? C20 C21 C22 C27 -0.7(4) . . . . ? C21 C22 C23 C24 179.6(3) . . . . ? C27 C22 C23 C24 0.3(4) . . . . ? C22 C23 C24 C25 -0.5(4) . . . . ? C23 C24 C25 C26 0.7(5) . . . . ? C24 C25 C26 C27 -0.7(4) . . . . ? C25 C26 C27 C28 179.4(2) . . . . ? C25 C26 C27 C22 0.4(4) . . . . ? C21 C22 C27 C28 1.4(3) . . . . ? C23 C22 C27 C28 -179.3(2) . . . . ? C21 C22 C27 C26 -179.6(2) . . . . ? C23 C22 C27 C26 -0.2(4) . . . . ? O2 C19 C28 C27 -179.48(19) . . . . ? C20 C19 C28 C27 0.9(4) . . . . ? O2 C19 C28 C29 1.0(3) . . . . ? C20 C19 C28 C29 -178.6(2) . . . . ? C26 C27 C28 C19 179.5(2) . . . . ? C22 C27 C28 C19 -1.5(3) . . . . ? C26 C27 C28 C29 -1.0(4) . . . . ? C22 C27 C28 C29 177.9(2) . . . . ? C19 C28 C29 C31 117.1(2) . . . . ? C27 C28 C29 C31 -62.3(3) . . . . ? C19 C28 C29 C30 -4.7(2) . . . . ? C27 C28 C29 C30 175.8(2) . . . . ? C19 O2 C30 N1 114.17(19) . . . . ? C19 O2 C30 C29 -6.5(2) . . . . ? O3 N1 C30 O2 178.3(2) . . . . ? O3' N1 C30 O2 -63.0(3) . . . . ? C12 N1 C30 O2 58.1(2) . . . . ? O3 N1 C30 C29 -63.5(3) . . . . ? O3' N1 C30 C29 55.2(3) . . . . ? C12 N1 C30 C29 176.37(19) . . . . ? C28 C29 C30 O2 6.7(2) . . . . ? C31 C29 C30 O2 -117.3(2) . . . . ? C28 C29 C30 N1 -112.3(2) . . . . ? C31 C29 C30 N1 123.8(2) . . . . ? C28 C29 C31 C32 -16.2(3) . . . . ? C30 C29 C31 C32 99.4(3) . . . . ? C28 C29 C31 C36 163.9(2) . . . . ? C30 C29 C31 C36 -80.5(3) . . . . ? C36 C31 C32 C33 -0.5(4) . . . . ? C29 C31 C32 C33 179.6(2) . . . . ? C31 C32 C33 C34 0.2(5) . . . . ? C32 C33 C34 C35 1.1(5) . . . . ? C33 C34 C35 C36 -2.0(5) . . . . ? C32 C31 C36 C35 -0.4(4) . . . . ? C29 C31 C36 C35 179.5(2) . . . . ? C34 C35 C36 C31 1.6(4) . . . . ? 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 O4 H4O N1 0.82 2.23 3.040(5) 172.4 . O4' H4O' O3' 0.82 2.16 2.768(7) 131.1 . _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.179 _refine_diff_density_min -0.158 _refine_diff_density_rms 0.031