# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Peter H Seeberger' _publ_contact_author_email SEEBERGER@ORG.CHEM.ETHZ.CH _publ_section_title ; Stereocontrolled synthesis of fully functionalized D-glucosamine monosaccharides via a domino nitro-Michael/Henry reaction ; loop_ _publ_author_name 'Peter H Seeberger' 'Alexander Adibekian' 'Jimmy van Rijn' 'Pierre Stallforth' 'Mattie S M Timmer' ; D.B.Werz ; # Attachment 'timm1.cif' data_timm1_seebe_05 _database_code_depnum_ccdc_archive 'CCDC 681201' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H15 N O6' _chemical_absolute_configuration syn _chemical_formula_sum 'C12 H15 N O6' _chemical_formula_weight 269.25 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 'P 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 5.1511(3) _cell_length_b 8.8875(5) _cell_length_c 13.8985(10) _cell_angle_alpha 90.00 _cell_angle_beta 95.959(3) _cell_angle_gamma 90.00 _cell_volume 632.84(7) _cell_formula_units_Z 2 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 998 _cell_measurement_theta_min 2.72 _cell_measurement_theta_max 25.02 _exptl_crystal_description 'Cut fragment' _exptl_crystal_colour colorless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.413 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 284 _exptl_absorpt_coefficient_mu 0.114 _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 223(2) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Kappa CCD' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_reflns_number 1895 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0560 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.72 _diffrn_reflns_theta_max 25.02 _reflns_number_total 1895 _reflns_number_gt 1686 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Kappa CCD' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo + Scalepak (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR97 (Altomare et Al., 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP (Johnson,1976)' _computing_publication_material SHELXL97 _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^)+(0.0508P)^2^+0.0939P] 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 riding _refine_ls_extinction_method SHELXL97 _refine_ls_extinction_coef 0.085(14) _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 ? _refine_ls_number_reflns 1895 _refine_ls_number_parameters 188 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0486 _refine_ls_R_factor_gt 0.0419 _refine_ls_wR_factor_ref 0.1090 _refine_ls_wR_factor_gt 0.1025 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 1.3512(5) 0.6512(3) 0.2040(2) 0.0389(6) Uani 1 d . . . H1A H 1.5116 0.7112 0.2120 0.025(6) Uiso 1 calc R . . H1B H 1.2970 0.6313 0.2684 0.050(8) Uiso 1 calc R . . C2 C 1.1393(5) 0.7381(3) 0.14415(17) 0.0341(6) Uani 1 d . . . H2A H 0.9804 0.6752 0.1330 0.019(6) Uiso 1 calc R . . C3 C 1.0752(5) 0.8837(3) 0.19518(17) 0.0318(6) Uani 1 d . . . H3A H 1.2376 0.9424 0.2106 0.044(8) Uiso 1 calc R . . C4 C 0.8751(5) 0.9809(3) 0.13505(17) 0.0365(6) Uani 1 d . . . H4A H 0.7260 0.9182 0.1083 0.037(7) Uiso 1 calc R . . C5 C 0.7796(6) 1.1059(4) 0.1965(2) 0.0435(7) Uani 1 d . . . H5A H 0.9195 1.1796 0.2113 0.040(7) Uiso 1 calc R . . H5B H 0.6318 1.1573 0.1604 0.070(11) Uiso 1 calc R . . O6 O 0.7000(3) 1.0466(2) 0.28516(12) 0.0420(5) Uani 1 d . . . C7 C 0.9091(5) 0.9689(3) 0.33750(17) 0.0341(6) Uani 1 d . . . H7A H 1.0625 1.0363 0.3479 0.044(8) Uiso 1 calc R . . O8 O 0.9741(3) 0.8403(2) 0.28384(11) 0.0316(4) Uani 1 d . . . O9 O 0.9917(4) 1.0529(3) 0.05821(13) 0.0523(6) Uani 1 d . . . H9A H 1.0772 0.9903 0.0303 0.070(16) Uiso 1 calc R . . N10 N 1.4021(5) 0.5059(3) 0.15556(18) 0.0457(6) Uani 1 d . . . O11 O 1.2297(4) 0.4143(3) 0.14387(17) 0.0594(6) Uani 1 d . . . O12 O 1.6141(5) 0.4845(4) 0.1305(3) 0.1205(14) Uani 1 d . . . O13 O 1.2253(4) 0.7794(2) 0.05384(13) 0.0472(5) Uani 1 d . . . H13A H 1.1579 0.7227 0.0108 0.065(16) Uiso 1 calc R . . C14 C 0.8303(4) 0.9196(3) 0.43294(17) 0.0321(6) Uani 1 d . . . C15 C 0.9758(5) 0.9623(4) 0.51729(19) 0.0430(7) Uani 1 d . . . H15A H 1.1222 1.0247 0.5145 0.046(9) Uiso 1 calc R . . C16 C 0.9081(6) 0.9139(4) 0.6069(2) 0.0497(8) Uani 1 d . . . H16A H 1.0095 0.9425 0.6641 0.065(10) Uiso 1 calc R . . C17 C 0.6932(5) 0.8244(4) 0.61115(19) 0.0452(7) Uani 1 d . . . H17A H 0.6474 0.7916 0.6715 0.058(9) Uiso 1 calc R . . C18 C 0.5440(6) 0.7820(4) 0.5279(2) 0.0452(7) Uani 1 d . . . H18A H 0.3968 0.7205 0.5313 0.061(10) Uiso 1 calc R . . C19 C 0.6106(5) 0.8302(4) 0.4388(2) 0.0430(7) Uani 1 d . . . H19A H 0.5068 0.8022 0.3820 0.060(9) Uiso 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 C1 0.0418(14) 0.0356(16) 0.0401(14) -0.0063(13) 0.0072(11) -0.0037(12) C2 0.0408(13) 0.0349(15) 0.0282(13) -0.0048(12) 0.0109(11) -0.0061(11) C3 0.0368(12) 0.0341(16) 0.0257(12) 0.0002(11) 0.0086(10) -0.0052(11) C4 0.0481(14) 0.0361(15) 0.0254(13) 0.0036(12) 0.0039(11) -0.0039(12) C5 0.0580(17) 0.0369(16) 0.0367(15) 0.0092(13) 0.0103(13) 0.0100(13) O6 0.0495(10) 0.0432(11) 0.0346(10) 0.0074(9) 0.0108(8) 0.0132(9) C7 0.0377(12) 0.0333(15) 0.0315(13) -0.0044(12) 0.0054(11) 0.0012(11) O8 0.0414(9) 0.0310(10) 0.0240(8) -0.0014(8) 0.0110(7) -0.0002(7) O9 0.0808(14) 0.0445(13) 0.0338(10) 0.0114(10) 0.0172(10) 0.0048(12) N10 0.0467(13) 0.0368(15) 0.0548(15) -0.0050(12) 0.0106(11) 0.0008(11) O11 0.0685(13) 0.0408(13) 0.0679(16) -0.0082(11) 0.0026(11) -0.0069(12) O12 0.0673(15) 0.080(2) 0.225(4) -0.069(3) 0.065(2) -0.0093(16) O13 0.0656(12) 0.0486(13) 0.0301(10) -0.0026(10) 0.0175(9) -0.0045(10) C14 0.0373(12) 0.0314(15) 0.0283(13) -0.0029(11) 0.0062(10) 0.0056(11) C15 0.0413(13) 0.0532(19) 0.0349(16) -0.0029(14) 0.0063(11) -0.0039(13) C16 0.0526(15) 0.068(2) 0.0281(14) -0.0036(14) 0.0028(12) 0.0066(16) C17 0.0555(16) 0.0503(19) 0.0321(14) 0.0075(14) 0.0149(12) 0.0128(15) C18 0.0517(16) 0.0411(17) 0.0459(17) 0.0024(14) 0.0188(13) -0.0006(13) C19 0.0479(15) 0.0440(17) 0.0374(14) -0.0038(14) 0.0057(11) -0.0058(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N10 1.492(4) . ? C1 C2 1.514(4) . ? C2 O13 1.422(3) . ? C2 C3 1.528(4) . ? C3 O8 1.439(3) . ? C3 C4 1.526(4) . ? C4 O9 1.430(3) . ? C4 C5 1.514(4) . ? C5 O6 1.438(3) . ? O6 C7 1.415(3) . ? C7 O8 1.424(3) . ? C7 C14 1.493(3) . ? N10 O12 1.196(3) . ? N10 O11 1.203(3) . ? C14 C15 1.378(4) . ? C14 C19 1.393(4) . ? C15 C16 1.397(4) . ? C16 C17 1.369(5) . ? C17 C18 1.373(4) . ? C18 C19 1.387(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 N10 C1 C2 110.1(2) . . ? O13 C2 C1 110.1(2) . . ? O13 C2 C3 107.0(2) . . ? C1 C2 C3 110.8(2) . . ? O8 C3 C4 109.69(19) . . ? O8 C3 C2 106.6(2) . . ? C4 C3 C2 113.1(2) . . ? O9 C4 C5 106.3(2) . . ? O9 C4 C3 110.5(2) . . ? C5 C4 C3 110.3(2) . . ? O6 C5 C4 110.7(2) . . ? C7 O6 C5 110.46(19) . . ? O6 C7 O8 109.29(18) . . ? O6 C7 C14 109.72(19) . . ? O8 C7 C14 109.3(2) . . ? C7 O8 C3 111.03(19) . . ? O12 N10 O11 122.4(3) . . ? O12 N10 C1 118.6(3) . . ? O11 N10 C1 119.0(2) . . ? C15 C14 C19 118.8(2) . . ? C15 C14 C7 120.1(2) . . ? C19 C14 C7 121.1(2) . . ? C14 C15 C16 120.7(3) . . ? C17 C16 C15 119.7(3) . . ? C16 C17 C18 120.5(3) . . ? C17 C18 C19 120.0(3) . . ? C18 C19 C14 120.4(3) . . ? 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 N10 C1 C2 O13 -64.6(3) . . . . ? N10 C1 C2 C3 177.2(2) . . . . ? O13 C2 C3 O8 176.73(18) . . . . ? C1 C2 C3 O8 -63.2(2) . . . . ? O13 C2 C3 C4 56.2(3) . . . . ? C1 C2 C3 C4 176.3(2) . . . . ? O8 C3 C4 O9 166.9(2) . . . . ? C2 C3 C4 O9 -74.3(3) . . . . ? O8 C3 C4 C5 49.7(3) . . . . ? C2 C3 C4 C5 168.5(2) . . . . ? O9 C4 C5 O6 -169.9(2) . . . . ? C3 C4 C5 O6 -50.1(3) . . . . ? C4 C5 O6 C7 57.9(3) . . . . ? C5 O6 C7 O8 -65.0(3) . . . . ? C5 O6 C7 C14 175.2(2) . . . . ? O6 C7 O8 C3 65.5(2) . . . . ? C14 C7 O8 C3 -174.46(18) . . . . ? C4 C3 O8 C7 -57.6(2) . . . . ? C2 C3 O8 C7 179.71(18) . . . . ? C2 C1 N10 O12 117.8(4) . . . . ? C2 C1 N10 O11 -62.8(3) . . . . ? O6 C7 C14 C15 -123.7(3) . . . . ? O8 C7 C14 C15 116.5(3) . . . . ? O6 C7 C14 C19 56.4(3) . . . . ? O8 C7 C14 C19 -63.4(3) . . . . ? C19 C14 C15 C16 1.5(4) . . . . ? C7 C14 C15 C16 -178.4(3) . . . . ? C14 C15 C16 C17 -0.7(5) . . . . ? C15 C16 C17 C18 0.0(5) . . . . ? C16 C17 C18 C19 -0.1(5) . . . . ? C17 C18 C19 C14 0.9(5) . . . . ? C15 C14 C19 C18 -1.6(4) . . . . ? C7 C14 C19 C18 178.3(3) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.187 _refine_diff_density_min -0.144 _refine_diff_density_rms 0.035 # Attachment 'timm2.cif' data_timm2_seebe_05 _database_code_depnum_ccdc_archive 'CCDC 681202' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H19 N O7' _chemical_absolute_configuration syn _chemical_formula_sum 'C15 H19 N O7' _chemical_formula_weight 325.31 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 'C 2' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 26.1806(4) _cell_length_b 4.7874(9) _cell_length_c 12.9169(2) _cell_angle_alpha 90.00 _cell_angle_beta 106.251(6) _cell_angle_gamma 90.00 _cell_volume 1554.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 203(2) _cell_measurement_reflns_used 1030 _cell_measurement_theta_min 2.61 _cell_measurement_theta_max 21.97 _exptl_crystal_description 'Cut fragment' _exptl_crystal_colour colorless _exptl_crystal_size_max 0.51 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.390 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 0.111 _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 203(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Kappa CCD' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_reflns_number 1816 _diffrn_reflns_av_R_equivalents 0.0350 _diffrn_reflns_av_sigmaI/netI 0.0575 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.61 _diffrn_reflns_theta_max 21.97 _reflns_number_total 1070 _reflns_number_gt 942 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Kappa CCD' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo + Scalepak (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR97 (Altomare et Al., 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP (Johnson,1976)' _computing_publication_material SHELXL97 _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^)+(0.0631P)^2^+1.0159P] 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 riding _refine_ls_extinction_method SHELXL97 _refine_ls_extinction_coef 0.010(2) _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 ? _refine_ls_number_reflns 1070 _refine_ls_number_parameters 209 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0529 _refine_ls_R_factor_gt 0.0445 _refine_ls_wR_factor_ref 0.1184 _refine_ls_wR_factor_gt 0.1130 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.044 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.76168(17) -0.0258(11) 0.2887(4) 0.0382(12) Uani 1 d . . . H1A H 0.7477 -0.1958 0.3149 0.046 Uiso 1 calc R . . C2 C 0.7992(2) -0.1192(12) 0.2219(4) 0.0462(14) Uani 1 d . . . H2A H 0.7812 -0.2649 0.1701 0.055 Uiso 1 calc R . . O3 O 0.84679(12) -0.2335(7) 0.2921(3) 0.0453(9) Uani 1 d . . . C4 C 0.87331(17) -0.0420(11) 0.3745(4) 0.0410(13) Uani 1 d . . . H4A H 0.8809 0.1348 0.3419 0.049 Uiso 1 calc R . . C5 C 0.83827(16) 0.0132(12) 0.4473(4) 0.0367(12) Uani 1 d . . . H5A H 0.8297 -0.1661 0.4769 0.044 Uiso 1 calc R . . C6 C 0.78737(16) 0.1543(11) 0.3857(4) 0.0370(13) Uani 1 d . . . H6A H 0.7952 0.3420 0.3618 0.044 Uiso 1 calc R . . C7 C 0.92474(18) -0.1738(12) 0.4416(4) 0.0468(14) Uani 1 d . . . H7A H 0.9175 -0.3550 0.4698 0.056 Uiso 1 calc R . . H7B H 0.9492 -0.2029 0.3973 0.056 Uiso 1 calc R . . O8 O 0.94794(11) 0.0148(8) 0.5291(3) 0.0465(10) Uani 1 d . . . C9 C 0.91383(17) 0.0634(12) 0.5949(4) 0.0427(13) Uani 1 d . . . H9A H 0.9058 -0.1155 0.6255 0.051 Uiso 1 calc R . . O10 O 0.86545(12) 0.1925(7) 0.5347(2) 0.0405(9) Uani 1 d . . . O11 O 0.75035(11) 0.1767(7) 0.4484(2) 0.0408(9) Uani 1 d . . . H11A H 0.7524 0.3349 0.4755 0.061 Uiso 1 calc R . . N12 N 0.71527(17) 0.1225(11) 0.2108(4) 0.0465(12) Uani 1 d . . . O13 O 0.70790(15) 0.3690(9) 0.2231(3) 0.0643(12) Uani 1 d . . . O14 O 0.68797(14) -0.0203(9) 0.1374(3) 0.0604(11) Uani 1 d . . . O15 O 0.80852(14) 0.1128(9) 0.1648(3) 0.0592(11) Uani 1 d . . . C16 C 0.8220(3) 0.042(2) 0.0659(5) 0.096(3) Uani 1 d . . . H16A H 0.8119 -0.1522 0.0474 0.115 Uiso 1 calc R . . H16B H 0.8008 0.1599 0.0075 0.115 Uiso 1 calc R . . C17 C 0.8750(3) 0.074(3) 0.0707(6) 0.118(4) Uani 1 d . . . H17A H 0.8803 0.0261 0.0015 0.177 Uiso 1 calc R . . H17B H 0.8965 -0.0475 0.1260 0.177 Uiso 1 calc R . . H17C H 0.8856 0.2669 0.0879 0.177 Uiso 1 calc R . . C18 C 0.94045(19) 0.2604(12) 0.6847(4) 0.0437(13) Uani 1 d . . . C19 C 0.9897(2) 0.3779(13) 0.6903(4) 0.0509(14) Uani 1 d . . . H19A H 1.0075 0.3319 0.6387 0.061 Uiso 1 calc R . . C20 C 1.0122(2) 0.5633(15) 0.7726(4) 0.0619(17) Uani 1 d . . . H20A H 1.0456 0.6421 0.7765 0.074 Uiso 1 calc R . . C21 C 0.9869(2) 0.6347(16) 0.8487(5) 0.0711(19) Uani 1 d . . . H21A H 1.0025 0.7634 0.9034 0.085 Uiso 1 calc R . . C22 C 0.9382(2) 0.5146(18) 0.8440(5) 0.0731(19) Uani 1 d . . . H22A H 0.9207 0.5600 0.8960 0.088 Uiso 1 calc R . . C23 C 0.9152(2) 0.3262(15) 0.7618(5) 0.0634(18) Uani 1 d . . . H23A H 0.8823 0.2435 0.7591 0.076 Uiso 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 C1 0.037(3) 0.032(3) 0.044(3) -0.001(3) 0.008(2) 0.002(2) C2 0.047(3) 0.048(3) 0.044(3) -0.003(3) 0.013(2) 0.001(3) O3 0.0435(19) 0.043(2) 0.0505(19) -0.011(2) 0.0152(17) 0.0010(18) C4 0.039(3) 0.035(3) 0.051(3) -0.002(3) 0.016(2) -0.004(2) C5 0.037(3) 0.033(3) 0.042(3) -0.004(3) 0.013(2) -0.003(2) C6 0.037(2) 0.040(3) 0.040(3) 0.002(3) 0.020(2) -0.001(2) C7 0.042(3) 0.051(4) 0.050(3) -0.009(3) 0.016(2) 0.003(3) O8 0.0351(17) 0.054(2) 0.052(2) -0.004(2) 0.0151(16) 0.0009(18) C9 0.035(3) 0.044(3) 0.048(3) 0.006(3) 0.010(2) 0.006(2) O10 0.0346(16) 0.043(2) 0.0437(19) -0.0032(17) 0.0101(15) -0.0013(16) O11 0.0359(17) 0.038(2) 0.0507(18) -0.0036(16) 0.0166(15) 0.0011(16) N12 0.046(3) 0.039(3) 0.051(3) 0.003(3) 0.007(2) 0.003(2) O13 0.069(3) 0.036(3) 0.072(3) 0.000(2) -0.007(2) 0.005(2) O14 0.056(2) 0.057(3) 0.056(2) -0.008(2) -0.0039(19) -0.001(2) O15 0.065(2) 0.067(3) 0.051(2) 0.011(2) 0.0259(18) -0.002(2) C16 0.099(5) 0.141(8) 0.059(4) -0.003(5) 0.041(4) -0.036(6) C17 0.071(4) 0.208(11) 0.083(5) 0.036(7) 0.035(4) 0.045(6) C18 0.044(3) 0.043(3) 0.041(3) 0.003(3) 0.006(2) -0.001(3) C19 0.053(3) 0.052(3) 0.048(3) 0.001(3) 0.014(3) -0.007(3) C20 0.062(3) 0.070(5) 0.048(3) 0.003(4) 0.008(3) -0.020(3) C21 0.080(4) 0.083(5) 0.043(3) -0.008(4) 0.005(3) -0.021(4) C22 0.070(4) 0.097(5) 0.054(3) -0.024(4) 0.020(3) -0.017(4) C23 0.052(3) 0.085(5) 0.054(3) -0.013(4) 0.015(3) -0.014(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.515(7) . ? C1 N12 1.519(6) . ? C1 C2 1.544(7) . ? C2 O15 1.392(7) . ? C2 O3 1.429(6) . ? O3 C4 1.429(6) . ? C4 C5 1.510(6) . ? C4 C7 1.519(7) . ? C5 O10 1.438(6) . ? C5 C6 1.507(6) . ? C6 O11 1.430(5) . ? C7 O8 1.441(6) . ? O8 C9 1.414(5) . ? C9 O10 1.428(5) . ? C9 C18 1.506(7) . ? N12 O13 1.213(6) . ? N12 O14 1.224(6) . ? O15 C16 1.458(7) . ? C16 C17 1.380(8) . ? C18 C23 1.377(7) . ? C18 C19 1.389(7) . ? C19 C20 1.384(8) . ? C20 C21 1.374(8) . ? C21 C22 1.384(9) . ? C22 C23 1.394(9) . ? 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 C6 C1 N12 111.7(4) . . ? C6 C1 C2 115.0(4) . . ? N12 C1 C2 106.3(4) . . ? O15 C2 O3 113.0(4) . . ? O15 C2 C1 107.3(4) . . ? O3 C2 C1 109.5(4) . . ? C2 O3 C4 112.5(4) . . ? O3 C4 C5 108.8(3) . . ? O3 C4 C7 109.1(4) . . ? C5 C4 C7 108.3(4) . . ? O10 C5 C6 108.5(4) . . ? O10 C5 C4 109.9(3) . . ? C6 C5 C4 110.5(4) . . ? O11 C6 C5 112.0(4) . . ? O11 C6 C1 107.2(3) . . ? C5 C6 C1 107.7(4) . . ? O8 C7 C4 107.4(4) . . ? C9 O8 C7 112.1(3) . . ? O8 C9 O10 110.9(4) . . ? O8 C9 C18 109.4(4) . . ? O10 C9 C18 107.3(4) . . ? C9 O10 C5 109.7(4) . . ? O13 N12 O14 124.4(5) . . ? O13 N12 C1 119.7(5) . . ? O14 N12 C1 115.9(5) . . ? C2 O15 C16 113.7(6) . . ? C17 C16 O15 115.0(6) . . ? C23 C18 C19 119.7(5) . . ? C23 C18 C9 119.2(5) . . ? C19 C18 C9 121.1(5) . . ? C20 C19 C18 119.3(5) . . ? C21 C20 C19 121.5(6) . . ? C20 C21 C22 119.2(6) . . ? C21 C22 C23 119.9(6) . . ? C18 C23 C22 120.4(6) . . ? 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 C6 C1 C2 O15 -73.6(5) . . . . ? N12 C1 C2 O15 50.6(5) . . . . ? C6 C1 C2 O3 49.5(6) . . . . ? N12 C1 C2 O3 173.6(4) . . . . ? O15 C2 O3 C4 62.9(5) . . . . ? C1 C2 O3 C4 -56.7(5) . . . . ? C2 O3 C4 C5 65.0(5) . . . . ? C2 O3 C4 C7 -177.1(4) . . . . ? O3 C4 C5 O10 176.6(4) . . . . ? C7 C4 C5 O10 58.2(5) . . . . ? O3 C4 C5 C6 -63.7(5) . . . . ? C7 C4 C5 C6 177.9(4) . . . . ? O10 C5 C6 O11 -67.1(5) . . . . ? C4 C5 C6 O11 172.4(4) . . . . ? O10 C5 C6 C1 175.2(3) . . . . ? C4 C5 C6 C1 54.7(5) . . . . ? N12 C1 C6 O11 69.3(5) . . . . ? C2 C1 C6 O11 -169.3(4) . . . . ? N12 C1 C6 C5 -170.0(3) . . . . ? C2 C1 C6 C5 -48.7(5) . . . . ? O3 C4 C7 O8 -175.1(4) . . . . ? C5 C4 C7 O8 -56.8(5) . . . . ? C4 C7 O8 C9 59.7(5) . . . . ? C7 O8 C9 O10 -62.1(5) . . . . ? C7 O8 C9 C18 179.8(4) . . . . ? O8 C9 O10 C5 60.5(5) . . . . ? C18 C9 O10 C5 179.9(3) . . . . ? C6 C5 O10 C9 179.8(3) . . . . ? C4 C5 O10 C9 -59.3(5) . . . . ? C6 C1 N12 O13 10.3(6) . . . . ? C2 C1 N12 O13 -115.9(5) . . . . ? C6 C1 N12 O14 -170.9(4) . . . . ? C2 C1 N12 O14 62.9(5) . . . . ? O3 C2 O15 C16 85.1(5) . . . . ? C1 C2 O15 C16 -154.0(4) . . . . ? C2 O15 C16 C17 -105.2(9) . . . . ? O8 C9 C18 C23 -176.9(5) . . . . ? O10 C9 C18 C23 62.8(6) . . . . ? O8 C9 C18 C19 3.6(7) . . . . ? O10 C9 C18 C19 -116.8(5) . . . . ? C23 C18 C19 C20 -1.1(8) . . . . ? C9 C18 C19 C20 178.4(5) . . . . ? C18 C19 C20 C21 -0.2(9) . . . . ? C19 C20 C21 C22 1.1(10) . . . . ? C20 C21 C22 C23 -0.7(10) . . . . ? C19 C18 C23 C22 1.5(9) . . . . ? C9 C18 C23 C22 -178.0(5) . . . . ? C21 C22 C23 C18 -0.6(10) . . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 21.97 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.170 _refine_diff_density_min -0.173 _refine_diff_density_rms 0.038