# Supplementary Material (ESI) for ChemComm # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 182/1789 data_global #======================================================== # 1. SUBMISSION DETAILS _publ_contact_author # Name and address of author for correspondence ; Dr. Richard Wightman Department of Chemistry Heriot-Watt University Edinburgh EH14 4AS ; _publ_contact_author_phone '0131 451-8039' _publ_contact_author_fax '0131 451 3180' _publ_contact_author_email R.Wightman@hw.ac.uk _publ_requested_journal 'J. Chem. Soc., Chem. Commun.' _publ_requested_coeditor_name ? _publ_contact_letter ; ; #======================================================================= # 2. PROCESSING SUMMARY (IUCr Office Use Only) _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_date_from_coeditor ? _journal_date_accepted ? _journal_date_printers_first ? _journal_date_printers_final ? _journal_date_proofs_out ? _journal_date_proofs_in ? _journal_coeditor_name ? _journal_coeditor_code ? _journal_coeditor_notes ; ? ; _journal_techeditor_code ? _journal_techeditor_notes ; ? ; _journal_coden_ASTM ? _journal_name_full ? _journal_year ? _journal_volume ? _journal_issue ? _journal_page_first ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? #================================================= # 3. TITLE AND AUTHOR LIST _publ_section_title ; Synthesis of aza-C-disaccharides using cycloaddition reactions of a functionalised cyclic nitrone ; # The loop structure below should contain the names and addresses of all # authors, in the required order of publication. Repeat as necessary. loop_ _publ_author_name _publ_author_address 'Wightman, Richard' #<--'Last name, first name' ; Department of Chemistry Heriot-Watt University Edinburgh EH14 4AS ; 'Duff, Fraser' ; Department of Chemistry Heriot-Watt University Edinburgh EH14 4AS ; 'Vivien, Vincent ' ; Department of Chemistry Heriot-Watt University Edinburgh EH14 4AS ; 'Rosair, Georgina M.' ; Department of Chemistry Heriot-Watt University Edinburgh EH14 4AS ; #============================================================= data_13 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H37 N O9' _chemical_formula_weight 507.57 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 14.549(4) _cell_length_b 5.907(2) _cell_length_c 16.345(6) _cell_angle_alpha 90.00 _cell_angle_beta 105.78(2) _cell_angle_gamma 90.00 _cell_volume 1351.8(8) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 27 _cell_measurement_theta_min 4.46 _cell_measurement_theta_max 11.28 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.247 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 544 _exptl_absorpt_coefficient_mu 0.094 _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 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _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_% ? _diffrn_reflns_number 4459 _diffrn_reflns_av_R_equivalents 0.0585 _diffrn_reflns_av_sigmaI/netI 0.1434 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.19 _diffrn_reflns_theta_max 22.50 _reflns_number_total 3524 _reflns_number_gt 2119 _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^)+(0.0723P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -1(3) _refine_ls_number_reflns 3524 _refine_ls_number_parameters 325 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1421 _refine_ls_R_factor_gt 0.0708 _refine_ls_wR_factor_ref 0.1709 _refine_ls_wR_factor_gt 0.1401 _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_restrained_S_all 1.011 _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 N1 N 0.1869(4) -0.6263(10) 0.3935(3) 0.0286(15) Uani 1 1 d . . . O1 O 0.4684(3) -0.1832(8) 0.3253(3) 0.0334(13) Uani 1 1 d . . . O2 O 0.5570(3) -0.6281(8) 0.2223(3) 0.0310(13) Uani 1 1 d . . . O3 O 0.4625(3) -0.5610(9) 0.0877(3) 0.0388(14) Uani 1 1 d . . . O4 O 0.2553(3) -0.5813(8) 0.0945(3) 0.0370(14) Uani 1 1 d . . . O5 O 0.4012(3) -0.5463(8) 0.3153(3) 0.0264(12) Uani 1 1 d . . . O6 O 0.2063(3) -0.4815(8) 0.3280(3) 0.0308(13) Uani 1 1 d . . . O9 O 0.2754(3) -0.9740(8) 0.5380(2) 0.0271(12) Uani 1 1 d . . . O10 O 0.1389(3) -1.1823(8) 0.5201(3) 0.0311(13) Uani 1 1 d . . . O11 O -0.0262(3) -0.9407(9) 0.4095(3) 0.0387(14) Uani 1 1 d . . . H11A H -0.0628 -0.8326 0.4036 0.058 Uiso 1 1 calc R . . C1 C 0.4820(5) -0.4118(13) 0.3113(4) 0.0270(19) Uani 1 1 d . . . H1A H 0.5378 -0.4648 0.3556 0.032 Uiso 1 1 calc R . . C2 C 0.5047(5) -0.4277(14) 0.2261(4) 0.0298(19) Uani 1 1 d . . . H2A H 0.5423 -0.2956 0.2185 0.036 Uiso 1 1 calc R . . C3 C 0.4199(5) -0.4577(14) 0.1471(4) 0.036(2) Uani 1 1 d . . . H3A H 0.3954 -0.3083 0.1257 0.043 Uiso 1 1 calc R . . C4 C 0.3387(5) -0.5970(13) 0.1643(4) 0.0288(19) Uani 1 1 d . . . H4A H 0.3585 -0.7558 0.1727 0.035 Uiso 1 1 calc R . . C5 C 0.3177(5) -0.5074(13) 0.2452(4) 0.0291(19) Uani 1 1 d . . . H5A H 0.3053 -0.3443 0.2392 0.035 Uiso 1 1 calc R . . C6 C 0.2340(5) -0.6221(12) 0.2649(4) 0.0262(19) Uani 1 1 d . . . H6A H 0.1809 -0.6313 0.2131 0.031 Uiso 1 1 calc R . . C7 C 0.2540(5) -0.8586(11) 0.3059(4) 0.0241(18) Uani 1 1 d . . . H7A H 0.2034 -0.9643 0.2802 0.029 Uiso 1 1 calc R . . H7B H 0.3145 -0.9184 0.3011 0.029 Uiso 1 1 calc R . . C8 C 0.2572(5) -0.8110(11) 0.3990(4) 0.0243(18) Uani 1 1 d . . . H8A H 0.3207 -0.7526 0.4281 0.029 Uiso 1 1 calc R . . C9 C 0.2372(5) -1.0140(12) 0.4479(4) 0.0265(18) Uani 1 1 d . . . H9A H 0.2682 -1.1476 0.4318 0.032 Uiso 1 1 calc R . . C10 C 0.1331(5) -1.0701(13) 0.4415(4) 0.0291(19) Uani 1 1 d . . . H10A H 0.1080 -1.1741 0.3940 0.035 Uiso 1 1 calc R . . C11 C 0.0700(5) -0.8611(12) 0.4316(4) 0.0269(19) Uani 1 1 d . . . H11B H 0.0834 -0.7807 0.4860 0.032 Uiso 1 1 calc R . . C12 C 0.0871(5) -0.7036(13) 0.3642(5) 0.032(2) Uani 1 1 d . . . H12A H 0.0763 -0.7826 0.3104 0.038 Uiso 1 1 calc R . . H12B H 0.0439 -0.5753 0.3564 0.038 Uiso 1 1 calc R . . C20 C 0.5518(5) -0.6591(14) 0.1336(4) 0.0292(19) Uani 1 1 d . . . C21 C 0.6310(5) -0.5435(14) 0.1080(4) 0.042(2) Uani 1 1 d . . . H21A H 0.6242 -0.5699 0.0487 0.063 Uiso 1 1 calc R . . H21B H 0.6912 -0.6025 0.1408 0.063 Uiso 1 1 calc R . . H21C H 0.6285 -0.3837 0.1179 0.063 Uiso 1 1 calc R . . C22 C 0.5497(6) -0.9099(14) 0.1182(5) 0.053(3) Uani 1 1 d . . . H22A H 0.5464 -0.9383 0.0596 0.080 Uiso 1 1 calc R . . H22B H 0.4948 -0.9743 0.1312 0.080 Uiso 1 1 calc R . . H22C H 0.6067 -0.9774 0.1538 0.080 Uiso 1 1 calc R . . C40 C 0.2441(9) -0.758(3) 0.0389(8) 0.163(8) Uani 1 1 d . . . H40A H 0.2375 -0.8965 0.0687 0.195 Uiso 1 1 calc R . . H40B H 0.3013 -0.7715 0.0196 0.195 Uiso 1 1 calc R . . C41 C 0.1598(8) -0.735(3) -0.0367(7) 0.081(4) Uani 1 1 d . . . C42 C 0.1530(12) -0.626(3) -0.1139(13) 0.138(6) Uani 1 1 d . . . H42A H 0.2048 -0.5425 -0.1202 0.166 Uiso 1 1 calc R . . C43 C 0.0700(11) -0.639(3) -0.1825(9) 0.110(5) Uani 1 1 d . . . H43A H 0.0671 -0.5761 -0.2354 0.132 Uiso 1 1 calc R . . C44 C -0.0022(11) -0.743(3) -0.1672(7) 0.123(6) Uani 1 1 d . . . H44A H -0.0557 -0.7603 -0.2134 0.147 Uiso 1 1 calc R . . C45 C -0.0092(11) -0.828(3) -0.0950(11) 0.150(6) Uani 1 1 d . . . H45A H -0.0656 -0.8830 -0.0864 0.179 Uiso 1 1 calc R . . C46 C 0.0807(14) -0.825(3) -0.0307(9) 0.159(7) Uani 1 1 d . . . H46A H 0.0823 -0.8955 0.0205 0.191 Uiso 1 1 calc R . . C90 C 0.2287(5) -1.1299(12) 0.5808(4) 0.0295(19) Uani 1 1 d . . . C91 C 0.2119(5) -1.0148(14) 0.6568(4) 0.039(2) Uani 1 1 d . . . H91A H 0.1808 -1.1176 0.6861 0.059 Uiso 1 1 calc R . . H91B H 0.1721 -0.8843 0.6389 0.059 Uiso 1 1 calc R . . H91C H 0.2719 -0.9684 0.6942 0.059 Uiso 1 1 calc R . . C92 C 0.2849(5) -1.3487(13) 0.6025(5) 0.042(2) Uani 1 1 d . . . H92A H 0.2518 -1.4500 0.6306 0.062 Uiso 1 1 calc R . . H92B H 0.3471 -1.3164 0.6394 0.062 Uiso 1 1 calc R . . H92C H 0.2914 -1.4179 0.5512 0.062 Uiso 1 1 calc R . . C100 C 0.4789(5) -0.1332(14) 0.4127(4) 0.044(2) Uani 1 1 d . . . H10B H 0.4686 0.0256 0.4190 0.066 Uiso 1 1 calc R . . H10C H 0.5422 -0.1729 0.4454 0.066 Uiso 1 1 calc R . . H10D H 0.4330 -0.2185 0.4324 0.066 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 N1 0.033(4) 0.031(4) 0.025(3) -0.006(3) 0.013(3) -0.004(3) O1 0.035(3) 0.020(3) 0.046(3) -0.004(3) 0.013(3) 0.002(3) O2 0.031(3) 0.033(3) 0.030(3) 0.002(2) 0.011(2) 0.008(3) O3 0.034(3) 0.065(4) 0.021(3) 0.004(3) 0.013(2) 0.001(3) O4 0.034(3) 0.048(4) 0.024(3) -0.002(3) 0.000(2) 0.004(3) O5 0.025(3) 0.029(3) 0.025(3) 0.002(2) 0.006(2) 0.001(2) O6 0.033(3) 0.029(3) 0.035(3) 0.001(3) 0.019(2) 0.000(3) O9 0.026(3) 0.033(3) 0.022(3) 0.004(2) 0.005(2) -0.007(2) O10 0.020(3) 0.040(3) 0.031(3) 0.006(3) 0.003(2) -0.008(3) O11 0.021(3) 0.045(3) 0.055(3) -0.009(3) 0.018(2) -0.001(3) C1 0.020(4) 0.037(5) 0.020(4) 0.007(4) 0.001(3) 0.000(4) C2 0.023(4) 0.035(5) 0.030(4) 0.010(4) 0.006(3) 0.003(4) C3 0.028(4) 0.035(5) 0.037(4) 0.011(4) -0.004(4) 0.003(4) C4 0.027(4) 0.035(5) 0.021(4) -0.005(4) 0.000(3) 0.001(4) C5 0.024(4) 0.032(5) 0.029(4) 0.000(4) 0.004(3) 0.000(4) C6 0.016(4) 0.036(5) 0.024(4) -0.016(4) 0.002(3) 0.006(4) C7 0.028(4) 0.017(4) 0.031(4) -0.004(3) 0.013(3) 0.005(3) C8 0.020(4) 0.019(4) 0.037(4) -0.003(3) 0.011(3) 0.007(4) C9 0.028(4) 0.031(5) 0.024(4) 0.001(4) 0.012(3) -0.003(4) C10 0.021(4) 0.038(5) 0.030(4) -0.008(4) 0.009(3) 0.007(4) C11 0.017(4) 0.031(5) 0.033(4) -0.006(4) 0.006(3) -0.005(4) C12 0.022(5) 0.028(5) 0.043(5) -0.002(4) 0.002(4) 0.005(4) C20 0.026(4) 0.037(5) 0.023(4) -0.006(4) 0.005(3) -0.004(4) C21 0.043(5) 0.045(5) 0.043(5) 0.012(4) 0.021(4) -0.002(4) C22 0.067(6) 0.063(7) 0.035(5) -0.006(5) 0.023(5) -0.011(5) C40 0.101(10) 0.205(16) 0.117(10) -0.121(11) -0.080(8) 0.083(10) C41 0.038(7) 0.137(12) 0.060(7) -0.042(8) -0.001(6) -0.004(7) C42 0.107(13) 0.149(16) 0.175(16) 0.013(13) 0.067(13) -0.007(12) C43 0.087(10) 0.130(13) 0.109(11) 0.062(10) 0.022(9) 0.029(10) C44 0.141(14) 0.180(16) 0.038(7) -0.012(8) 0.007(8) -0.069(12) C45 0.113(13) 0.169(17) 0.154(15) 0.014(13) 0.013(12) -0.050(12) C46 0.132(14) 0.188(18) 0.121(13) 0.063(12) -0.027(12) 0.010(14) C90 0.024(4) 0.030(5) 0.035(4) 0.004(4) 0.008(4) -0.003(4) C91 0.040(5) 0.039(5) 0.038(4) -0.004(4) 0.010(4) -0.003(4) C92 0.033(5) 0.039(5) 0.050(5) 0.006(4) 0.007(4) -0.007(4) C100 0.030(5) 0.053(6) 0.046(5) -0.012(5) 0.006(4) 0.005(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 O6 1.457(7) . ? N1 C12 1.472(8) . ? N1 C8 1.482(8) . ? O1 C1 1.392(9) . ? O1 C100 1.424(8) . ? O2 C2 1.417(8) . ? O2 C20 1.443(8) . ? O3 C3 1.423(8) . ? O3 C20 1.434(8) . ? O4 C40 1.364(11) . ? O4 C4 1.425(7) . ? O5 C1 1.436(8) . ? O5 C5 1.444(7) . ? O6 C6 1.464(7) . ? O9 C90 1.434(8) . ? O9 C9 1.446(7) . ? O10 C10 1.427(8) . ? O10 C90 1.443(8) . ? O11 C11 1.427(8) . ? C1 C2 1.520(9) . ? C2 C3 1.534(9) . ? C3 C4 1.527(10) . ? C4 C5 1.531(9) . ? C5 C6 1.502(9) . ? C6 C7 1.543(9) . ? C7 C8 1.536(9) . ? C8 C9 1.512(9) . ? C9 C10 1.525(9) . ? C10 C11 1.521(9) . ? C11 C12 1.514(9) . ? C20 C21 1.495(9) . ? C20 C22 1.502(11) . ? C40 C41 1.492(13) . ? C41 C46 1.296(18) . ? C41 C42 1.395(18) . ? C42 C43 1.409(19) . ? C43 C44 1.300(16) . ? C44 C45 1.310(17) . ? C45 C46 1.438(18) . ? C90 C91 1.494(9) . ? C90 C92 1.519(10) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O6 N1 C12 108.3(5) . . ? O6 N1 C8 102.0(5) . . ? C12 N1 C8 113.3(5) . . ? C1 O1 C100 112.6(5) . . ? C2 O2 C20 105.5(5) . . ? C3 O3 C20 108.5(5) . . ? C40 O4 C4 113.9(6) . . ? C1 O5 C5 113.5(5) . . ? N1 O6 C6 109.3(5) . . ? C90 O9 C9 106.9(5) . . ? C10 O10 C90 109.9(5) . . ? O1 C1 O5 112.0(5) . . ? O1 C1 C2 106.7(6) . . ? O5 C1 C2 113.1(6) . . ? O2 C2 C1 110.1(5) . . ? O2 C2 C3 100.7(6) . . ? C1 C2 C3 116.9(6) . . ? O3 C3 C4 113.4(6) . . ? O3 C3 C2 102.9(5) . . ? C4 C3 C2 113.1(6) . . ? O4 C4 C3 110.5(5) . . ? O4 C4 C5 110.0(5) . . ? C3 C4 C5 108.6(6) . . ? O5 C5 C6 108.3(5) . . ? O5 C5 C4 108.0(5) . . ? C6 C5 C4 113.1(6) . . ? O6 C6 C5 106.8(5) . . ? O6 C6 C7 105.2(5) . . ? C5 C6 C7 115.7(6) . . ? C8 C7 C6 102.5(5) . . ? N1 C8 C9 112.8(5) . . ? N1 C8 C7 103.9(5) . . ? C9 C8 C7 114.8(6) . . ? O9 C9 C8 109.4(5) . . ? O9 C9 C10 101.8(5) . . ? C8 C9 C10 117.8(6) . . ? O10 C10 C11 111.0(5) . . ? O10 C10 C9 103.0(5) . . ? C11 C10 C9 113.0(6) . . ? O11 C11 C12 111.2(5) . . ? O11 C11 C10 106.4(6) . . ? C12 C11 C10 111.2(6) . . ? N1 C12 C11 107.3(5) . . ? O3 C20 O2 105.5(5) . . ? O3 C20 C21 109.1(6) . . ? O2 C20 C21 113.0(6) . . ? O3 C20 C22 109.7(6) . . ? O2 C20 C22 106.7(6) . . ? C21 C20 C22 112.7(7) . . ? O4 C40 C41 113.8(10) . . ? C46 C41 C42 114.3(12) . . ? C46 C41 C40 116.5(15) . . ? C42 C41 C40 129.2(15) . . ? C41 C42 C43 122.0(13) . . ? C44 C43 C42 115.8(13) . . ? C43 C44 C45 128.2(14) . . ? C44 C45 C46 112.1(15) . . ? C41 C46 C45 126.8(15) . . ? O9 C90 O10 105.2(5) . . ? O9 C90 C91 108.6(6) . . ? O10 C90 C91 110.3(6) . . ? O9 C90 C92 111.3(5) . . ? O10 C90 C92 107.9(6) . . ? C91 C90 C92 113.1(6) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 22.50 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.266 _refine_diff_density_min -0.265 _refine_diff_density_rms 0.059 #===end data_18 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H35 N O10' _chemical_formula_weight 485.52 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 5.4170(10) _cell_length_b 25.006(4) _cell_length_c 9.0510(10) _cell_angle_alpha 90.00 _cell_angle_beta 96.870(10) _cell_angle_gamma 90.00 _cell_volume 1217.2(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 32 _cell_measurement_theta_min 6.487 _cell_measurement_theta_max 24.999 _exptl_crystal_description 'triangular plate' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.66 _exptl_crystal_size_mid 0.42 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.325 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 520 _exptl_absorpt_coefficient_mu 0.104 _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 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _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_% ? _diffrn_reflns_number 5108 _diffrn_reflns_av_R_equivalents 0.0232 _diffrn_reflns_av_sigmaI/netI 0.0275 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.27 _diffrn_reflns_theta_max 24.98 _reflns_number_total 2305 _reflns_number_gt 2222 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens XSCANS' _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^)+(0.0524P)^2^+0.1525P] 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 3.9(17) _refine_ls_number_reflns 2305 _refine_ls_number_parameters 308 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0323 _refine_ls_R_factor_gt 0.0305 _refine_ls_wR_factor_ref 0.0830 _refine_ls_wR_factor_gt 0.0815 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _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 N13 N -1.8175(4) -1.23291(8) -1.3713(2) 0.0265(4) Uani 1 1 d . . . O1 O -1.8285(3) -1.34230(9) -0.7692(2) 0.0370(5) Uani 1 1 d . . . O2 O -1.4710(3) -1.36871(8) -0.85538(17) 0.0275(4) Uani 1 1 d . . . O3 O -1.7152(3) -1.47510(7) -1.09511(19) 0.0290(4) Uani 1 1 d . . . O4 O -1.9432(3) -1.41893(7) -1.25180(19) 0.0282(4) Uani 1 1 d . . . O6 O -2.0076(3) -1.35134(7) -1.01417(18) 0.0263(4) Uani 1 1 d . . . O9 O -1.7069(3) -1.12004(7) -1.23227(17) 0.0251(4) Uani 1 1 d . . . O10 O -2.0266(3) -1.07649(7) -1.37126(19) 0.0264(4) Uani 1 1 d . . . O11 O -2.2306(3) -1.14592(8) -1.62301(18) 0.0275(4) Uani 1 1 d . . . O12 O -1.9945(4) -1.16587(9) -1.8044(2) 0.0410(5) Uani 1 1 d . . . O13 O -1.8245(4) -1.29001(7) -1.34558(19) 0.0345(4) Uani 1 1 d . . . C1 C -1.8985(4) -1.37829(9) -0.8865(2) 0.0221(5) Uani 1 1 d . . . H1 H -2.0184 -1.4040 -0.8548 0.027 Uiso 1 1 calc R . . C2 C -1.6550(4) -1.40765(10) -0.9045(2) 0.0223(4) Uani 1 1 d . . . H2 H -1.6371 -1.4389 -0.8389 0.027 Uiso 1 1 calc R . . C3 C -1.6105(4) -1.42369(10) -1.0625(2) 0.0226(5) Uani 1 1 d . . . H3 H -1.4316 -1.4246 -1.0700 0.027 Uiso 1 1 calc R . . C4 C -1.7408(4) -1.38704(10) -1.1840(2) 0.0244(5) Uani 1 1 d . . . H4 H -1.6277 -1.3778 -1.2568 0.029 Uiso 1 1 calc R . . C5 C -1.8428(4) -1.33705(10) -1.1191(2) 0.0239(5) Uani 1 1 d . . . H5 H -1.7045 -1.3162 -1.0685 0.029 Uiso 1 1 calc R . . C6 C -1.9921(5) -1.30188(10) -1.2339(3) 0.0278(5) Uani 1 1 d . . . H6 H -2.1417 -1.3205 -1.2790 0.033 Uiso 1 1 calc R . . C7 C -2.0582(5) -1.24769(10) -1.1709(3) 0.0284(5) Uani 1 1 d . . . H7A H -2.0462 -1.2485 -1.0631 0.034 Uiso 1 1 calc R . . H7B H -2.2241 -1.2364 -1.2110 0.034 Uiso 1 1 calc R . . C8 C -1.8588(5) -1.21134(10) -1.2244(3) 0.0255(5) Uani 1 1 d . . . H8 H -1.7050 -1.2159 -1.1567 0.031 Uiso 1 1 calc R . . C9 C -1.9259(4) -1.15222(10) -1.2293(2) 0.0230(5) Uani 1 1 d . . . H9 H -2.0055 -1.1431 -1.1409 0.028 Uiso 1 1 calc R . . C10 C -2.0877(4) -1.13213(9) -1.3682(3) 0.0230(5) Uani 1 1 d . . . H10 H -2.2639 -1.1365 -1.3561 0.028 Uiso 1 1 calc R . . C11 C -2.0301(4) -1.16042(10) -1.5086(3) 0.0234(5) Uani 1 1 d . . . H11 H -1.8704 -1.1481 -1.5365 0.028 Uiso 1 1 calc R . . C12 C -2.0252(5) -1.22068(10) -1.4862(3) 0.0277(5) Uani 1 1 d . . . H12A H -2.1809 -1.2328 -1.4547 0.033 Uiso 1 1 calc R . . H12B H -2.0018 -1.2386 -1.5786 0.033 Uiso 1 1 calc R . . C13 C -1.8613(5) -1.47289(10) -1.2383(3) 0.0260(5) Uani 1 1 d . . . C14 C -1.7049(5) -1.48682(12) -1.3618(3) 0.0355(6) Uani 1 1 d . . . H14A H -1.6522 -1.5234 -1.3517 0.053 Uiso 1 1 calc R . . H14B H -1.5616 -1.4639 -1.3550 0.053 Uiso 1 1 calc R . . H14C H -1.8021 -1.4819 -1.4567 0.053 Uiso 1 1 calc R . . C15 C -2.0807(5) -1.50945(11) -1.2368(3) 0.0333(6) Uani 1 1 d . . . H15A H -2.0244 -1.5458 -1.2285 0.050 Uiso 1 1 calc R . . H15B H -2.1905 -1.5051 -1.3274 0.050 Uiso 1 1 calc R . . H15C H -2.1677 -1.5008 -1.1535 0.050 Uiso 1 1 calc R . . C16 C -1.7955(4) -1.06815(10) -1.2765(3) 0.0248(5) Uani 1 1 d . . . C17 C -1.6095(5) -1.04177(11) -1.3636(3) 0.0325(5) Uani 1 1 d . . . H17A H -1.6679 -1.0068 -1.3943 0.049 Uiso 1 1 calc R . . H17B H -1.5892 -1.0630 -1.4497 0.049 Uiso 1 1 calc R . . H17C H -1.4528 -1.0387 -1.3023 0.049 Uiso 1 1 calc R . . C18 C -1.8485(6) -1.03511(11) -1.1428(3) 0.0377(6) Uani 1 1 d . . . H18A H -1.9081 -1.0004 -1.1756 0.056 Uiso 1 1 calc R . . H18B H -1.6985 -1.0313 -1.0755 0.056 Uiso 1 1 calc R . . H18C H -1.9723 -1.0528 -1.0929 0.056 Uiso 1 1 calc R . . C19 C -2.1878(4) -1.15042(10) -1.7668(3) 0.0279(5) Uani 1 1 d . . . C21 C -2.4092(5) -1.13223(13) -1.8691(3) 0.0404(7) Uani 1 1 d . . . H21A H -2.5393 -1.1218 -1.8117 0.061 Uiso 1 1 calc R . . H21B H -2.4667 -1.1609 -1.9349 0.061 Uiso 1 1 calc R . . H21C H -2.3638 -1.1023 -1.9264 0.061 Uiso 1 1 calc R . . C22 C -1.5635(4) -1.33725(11) -0.7431(3) 0.0298(5) Uani 1 1 d . . . C23 C -1.4699(6) -1.35800(15) -0.5903(3) 0.0447(7) Uani 1 1 d . . . H23A H -1.5338 -1.3361 -0.5164 0.067 Uiso 1 1 calc R . . H23B H -1.2915 -1.3569 -0.5764 0.067 Uiso 1 1 calc R . . H23C H -1.5249 -1.3942 -0.5808 0.067 Uiso 1 1 calc R . . C24 C -1.4883(7) -1.27956(13) -0.7650(4) 0.0512(8) Uani 1 1 d . . . H24A H -1.5492 -1.2575 -0.6904 0.077 Uiso 1 1 calc R . . H24B H -1.5579 -1.2676 -0.8619 0.077 Uiso 1 1 calc R . . H24C H -1.3104 -1.2771 -0.7566 0.077 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 N13 0.0390(11) 0.0205(10) 0.0208(9) 0.0039(7) 0.0066(8) 0.0099(9) O1 0.0267(9) 0.0494(11) 0.0344(9) -0.0210(9) 0.0015(7) 0.0049(8) O2 0.0216(8) 0.0349(9) 0.0258(8) -0.0099(7) 0.0024(6) -0.0029(7) O3 0.0379(9) 0.0194(8) 0.0270(8) -0.0021(7) -0.0073(7) 0.0035(7) O4 0.0324(9) 0.0242(8) 0.0259(8) -0.0020(7) -0.0058(7) 0.0070(7) O6 0.0265(8) 0.0266(9) 0.0267(8) 0.0055(7) 0.0072(6) 0.0060(7) O9 0.0261(8) 0.0240(8) 0.0240(8) 0.0028(6) -0.0019(6) 0.0029(7) O10 0.0262(8) 0.0192(8) 0.0320(9) 0.0030(7) -0.0042(7) 0.0028(7) O11 0.0264(8) 0.0318(9) 0.0229(8) 0.0034(7) -0.0031(6) 0.0026(7) O12 0.0380(10) 0.0569(13) 0.0282(9) 0.0019(9) 0.0037(8) 0.0011(10) O13 0.0582(12) 0.0221(9) 0.0262(8) 0.0038(7) 0.0163(8) 0.0133(8) C1 0.0220(10) 0.0232(12) 0.0217(10) 0.0019(9) 0.0048(8) -0.0015(9) C2 0.0221(10) 0.0222(11) 0.0219(10) 0.0012(9) 0.0004(8) 0.0007(9) C3 0.0213(10) 0.0212(11) 0.0253(11) -0.0029(9) 0.0030(9) 0.0033(9) C4 0.0296(11) 0.0231(11) 0.0208(10) -0.0007(9) 0.0050(9) 0.0017(10) C5 0.0303(11) 0.0206(11) 0.0213(10) 0.0011(9) 0.0053(9) 0.0011(10) C6 0.0370(13) 0.0225(12) 0.0241(11) 0.0027(9) 0.0048(10) 0.0063(10) C7 0.0398(13) 0.0216(11) 0.0250(11) 0.0045(10) 0.0091(10) 0.0079(10) C8 0.0327(12) 0.0246(12) 0.0193(11) 0.0039(9) 0.0034(9) 0.0072(10) C9 0.0279(11) 0.0220(11) 0.0195(10) 0.0011(8) 0.0043(9) 0.0035(9) C10 0.0234(10) 0.0204(11) 0.0253(11) 0.0022(8) 0.0031(9) 0.0025(9) C11 0.0241(11) 0.0240(12) 0.0211(10) 0.0037(9) -0.0018(8) 0.0025(9) C12 0.0385(13) 0.0234(12) 0.0210(11) -0.0004(9) 0.0033(9) 0.0007(10) C13 0.0300(12) 0.0258(12) 0.0209(11) -0.0050(9) -0.0024(9) 0.0053(10) C14 0.0360(13) 0.0356(15) 0.0351(13) -0.0121(11) 0.0056(11) 0.0017(11) C15 0.0322(13) 0.0338(14) 0.0332(13) -0.0085(11) 0.0008(10) -0.0008(11) C16 0.0264(11) 0.0233(12) 0.0232(11) 0.0016(9) -0.0027(9) 0.0022(9) C17 0.0294(12) 0.0288(12) 0.0395(14) 0.0067(11) 0.0052(10) 0.0021(10) C18 0.0478(17) 0.0287(14) 0.0365(14) -0.0071(11) 0.0051(12) 0.0023(12) C19 0.0307(12) 0.0278(12) 0.0239(11) 0.0055(9) -0.0023(9) -0.0062(10) C21 0.0399(14) 0.0525(18) 0.0258(13) 0.0052(12) -0.0087(11) -0.0021(13) C22 0.0280(12) 0.0348(14) 0.0263(12) -0.0112(11) 0.0015(9) 0.0010(11) C23 0.0485(16) 0.0595(19) 0.0254(12) -0.0091(12) 0.0012(11) 0.0122(15) C24 0.065(2) 0.0400(17) 0.0471(17) -0.0185(14) 0.0000(14) -0.0136(15) _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 N13 O13 1.448(3) . ? N13 C12 1.470(3) . ? N13 C8 1.476(3) . ? O1 C1 1.409(3) . ? O1 C22 1.432(3) . ? O2 C22 1.423(3) . ? O2 C2 1.426(3) . ? O3 C3 1.422(3) . ? O3 C13 1.436(3) . ? O4 C13 1.421(3) . ? O4 C4 1.433(3) . ? O6 C1 1.406(3) . ? O6 C5 1.424(3) . ? O9 C16 1.424(3) . ? O9 C9 1.436(3) . ? O10 C10 1.431(3) . ? O10 C16 1.446(3) . ? O11 C19 1.354(3) . ? O11 C11 1.454(3) . ? O12 C19 1.203(3) . ? O13 C6 1.468(3) . ? C1 C2 1.535(3) . ? C2 C3 1.532(3) . ? C3 C4 1.537(3) . ? C4 C5 1.513(3) . ? C5 C6 1.519(3) . ? C6 C7 1.529(3) . ? C7 C8 1.534(4) . ? C8 C9 1.522(3) . ? C9 C10 1.529(3) . ? C10 C11 1.518(3) . ? C11 C12 1.520(3) . ? C13 C15 1.501(4) . ? C13 C14 1.522(3) . ? C16 C17 1.504(4) . ? C16 C18 1.521(3) . ? C19 C21 1.496(4) . ? C22 C23 1.507(4) . ? C22 C24 1.518(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 O13 N13 C12 106.64(19) . . ? O13 N13 C8 101.90(17) . . ? C12 N13 C8 112.06(19) . . ? C1 O1 C22 110.76(18) . . ? C22 O2 C2 107.92(17) . . ? C3 O3 C13 108.40(19) . . ? C13 O4 C4 106.03(18) . . ? C1 O6 C5 115.66(17) . . ? C16 O9 C9 105.34(17) . . ? C10 O10 C16 108.34(18) . . ? C19 O11 C11 117.70(18) . . ? N13 O13 C6 109.89(17) . . ? O6 C1 O1 111.2(2) . . ? O6 C1 C2 115.09(17) . . ? O1 C1 C2 103.21(18) . . ? O2 C2 C3 106.74(18) . . ? O2 C2 C1 102.57(19) . . ? C3 C2 C1 117.23(18) . . ? O3 C3 C2 109.11(19) . . ? O3 C3 C4 104.65(18) . . ? C2 C3 C4 113.69(18) . . ? O4 C4 C5 109.3(2) . . ? O4 C4 C3 103.72(18) . . ? C5 C4 C3 111.87(18) . . ? O6 C5 C4 109.8(2) . . ? O6 C5 C6 106.03(19) . . ? C4 C5 C6 113.70(19) . . ? O13 C6 C5 105.39(19) . . ? O13 C6 C7 105.60(19) . . ? C5 C6 C7 112.8(2) . . ? C6 C7 C8 101.69(19) . . ? N13 C8 C9 112.99(19) . . ? N13 C8 C7 104.84(19) . . ? C9 C8 C7 114.2(2) . . ? O9 C9 C8 110.49(19) . . ? O9 C9 C10 101.18(17) . . ? C8 C9 C10 117.0(2) . . ? O10 C10 C11 111.46(19) . . ? O10 C10 C9 102.95(19) . . ? C11 C10 C9 112.34(19) . . ? O11 C11 C10 105.62(18) . . ? O11 C11 C12 110.0(2) . . ? C10 C11 C12 110.64(19) . . ? N13 C12 C11 107.5(2) . . ? O4 C13 O3 104.31(18) . . ? O4 C13 C15 109.8(2) . . ? O3 C13 C15 108.7(2) . . ? O4 C13 C14 110.5(2) . . ? O3 C13 C14 111.0(2) . . ? C15 C13 C14 112.2(2) . . ? O9 C16 O10 105.90(19) . . ? O9 C16 C17 108.82(19) . . ? O10 C16 C17 109.8(2) . . ? O9 C16 C18 111.15(19) . . ? O10 C16 C18 108.5(2) . . ? C17 C16 C18 112.4(2) . . ? O12 C19 O11 123.6(2) . . ? O12 C19 C21 125.7(2) . . ? O11 C19 C21 110.7(2) . . ? O2 C22 O1 105.38(18) . . ? O2 C22 C23 110.9(2) . . ? O1 C22 C23 110.0(2) . . ? O2 C22 C24 108.0(2) . . ? O1 C22 C24 110.0(2) . . ? C23 C22 C24 112.4(2) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.98 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.269 _refine_diff_density_min -0.182 _refine_diff_density_rms 0.040