Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'P. Jenkins' _publ_contact_author_address ; Department of Chemistry University of Leicester University Road Leicester LE1 7RH UNITED KINGDOM ; _publ_contact_author_email KIN@LE.AC.UK _publ_section_title ; Synthesis, Glycosidase Activity and X-ray Crystallography of 3-Amino-sugars ; loop_ _publ_author_name 'P. Jenkins' 'Daniel P. G. Emmerson' 'Emma L. Evinson' 'Vanessa L. Maxwell' data_02189 _database_code_depnum_ccdc_archive 'CCDC 604070' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H26 N2 O6' _chemical_formula_weight 306.36 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 Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)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 10.2890(1) _cell_length_b 20.1092(2) _cell_length_c 7.4282(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1536.92(9) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 8236 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.075 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.324 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 664 _exptl_absorpt_coefficient_mu 0.104 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.917 _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_process_details ; absorption correction by SORTAV ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12656 _diffrn_reflns_av_R_equivalents 0.0470 _diffrn_reflns_av_sigmaI/netI 0.0321 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.92 _diffrn_reflns_theta_max 24.99 _reflns_number_total 2690 _reflns_number_gt 2576 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0412P)^2^+0.4011P] 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 constrained _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.2(9) _refine_ls_number_reflns 2690 _refine_ls_number_parameters 191 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0346 _refine_ls_R_factor_gt 0.0324 _refine_ls_wR_factor_ref 0.0792 _refine_ls_wR_factor_gt 0.0775 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _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 0.72153(10) 0.72023(5) 0.41789(15) 0.0145(3) Uani 1 1 d . . . O2 O 0.52756(12) 0.76686(5) 0.66705(16) 0.0204(3) Uani 1 1 d . . . H2 H 0.4503 0.7737 0.6870 0.031 Uiso 1 1 calc R . . O3 O 0.42808(11) 0.68132(6) 0.15195(16) 0.0198(3) Uani 1 1 d . . . H3 H 0.3916 0.6468 0.1815 0.030 Uiso 1 1 calc R . . O4 O 0.82970(11) 0.72262(6) 0.07522(16) 0.0221(3) Uani 1 1 d . . . H4 H 0.8537 0.7440 -0.0128 0.033 Uiso 1 1 calc R . . O5 O 0.17545(13) 0.50641(6) -0.09862(17) 0.0299(3) Uani 1 1 d . . . O1' O 0.72226(11) 0.62269(5) 0.59212(15) 0.0165(3) Uani 1 1 d . . . N1 N 0.46102(13) 0.60086(6) 0.45556(18) 0.0152(3) Uani 1 1 d . . . H1A H 0.5249 0.5859 0.4936 0.018 Uiso 1 1 d R . . N2 N 0.24364(13) 0.56977(6) 0.23443(19) 0.0158(3) Uani 1 1 d . . . C1 C 0.69052(15) 0.69116(8) 0.5865(2) 0.0146(3) Uani 1 1 d . . . H1 H 0.7408 0.7140 0.6799 0.018 Uiso 1 1 calc R . . C1' C 0.85954(17) 0.61100(9) 0.5864(3) 0.0260(4) Uani 1 1 d . . . H1'1 H 0.9008 0.6345 0.6833 0.039 Uiso 1 1 calc R . . H1'2 H 0.8937 0.6265 0.4736 0.039 Uiso 1 1 calc R . . H1'3 H 0.8761 0.5642 0.5983 0.039 Uiso 1 1 calc R . . C2 C 0.54720(15) 0.69802(8) 0.6317(2) 0.0154(4) Uani 1 1 d . . . H2A H 0.5278 0.6723 0.7405 0.018 Uiso 1 1 calc R . . C3 C 0.46062(16) 0.67372(7) 0.4769(2) 0.0148(4) Uani 1 1 d . . . H3A H 0.3712 0.6879 0.5016 0.018 Uiso 1 1 calc R . . C4 C 0.50374(16) 0.70561(8) 0.2995(2) 0.0148(3) Uani 1 1 d . . . H4A H 0.4888 0.7536 0.3089 0.018 Uiso 1 1 calc R . . C5 C 0.64872(16) 0.69478(8) 0.2666(2) 0.0137(3) Uani 1 1 d . . . H5 H 0.6669 0.6473 0.2497 0.016 Uiso 1 1 calc R . . C6 C 0.69449(16) 0.73385(9) 0.1048(2) 0.0196(4) Uani 1 1 d . . . H6A H 0.6457 0.7203 -0.0007 0.024 Uiso 1 1 calc R . . H6B H 0.6792 0.7809 0.1246 0.024 Uiso 1 1 calc R . . C7 C 0.34874(17) 0.56793(8) 0.5368(2) 0.0177(4) Uani 1 1 d . . . H7A H 0.3367 0.5844 0.6584 0.021 Uiso 1 1 calc R . . H7B H 0.3651 0.5205 0.5438 0.021 Uiso 1 1 calc R . . C8 C 0.22528(16) 0.58008(8) 0.4285(2) 0.0175(4) Uani 1 1 d . . . H8A H 0.1578 0.5503 0.4712 0.021 Uiso 1 1 calc R . . H8B H 0.1961 0.6253 0.4489 0.021 Uiso 1 1 calc R . . C9 C 0.12055(17) 0.58433(9) 0.1413(2) 0.0206(4) Uani 1 1 d . . . H9A H 0.0961 0.6302 0.1627 0.025 Uiso 1 1 calc R . . H9B H 0.0523 0.5560 0.1888 0.025 Uiso 1 1 calc R . . C10 C 0.1347(2) 0.57256(9) -0.0586(3) 0.0281(4) Uani 1 1 d . . . H10C H 0.0520 0.5810 -0.1170 0.034 Uiso 1 1 calc R . . H10D H 0.1976 0.6037 -0.1070 0.034 Uiso 1 1 calc R . . C9' C 0.28284(18) 0.50126(9) 0.1926(2) 0.0209(4) Uani 1 1 d . . . H9'1 H 0.2186 0.4705 0.2392 0.025 Uiso 1 1 calc R . . H9'2 H 0.3654 0.4916 0.2499 0.025 Uiso 1 1 calc R . . C10' C 0.29532(19) 0.49240(10) -0.0090(2) 0.0264(4) Uani 1 1 d . . . H10A H 0.3624 0.5219 -0.0543 0.032 Uiso 1 1 calc R . . H10B H 0.3214 0.4471 -0.0351 0.032 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 O1 0.0144(6) 0.0162(6) 0.0130(6) 0.0018(4) -0.0019(5) -0.0030(4) O2 0.0187(6) 0.0153(6) 0.0271(6) -0.0059(5) 0.0030(5) -0.0008(5) O3 0.0184(6) 0.0219(6) 0.0190(6) 0.0052(5) -0.0076(5) -0.0051(5) O4 0.0179(6) 0.0314(7) 0.0169(6) 0.0073(5) 0.0037(5) -0.0031(5) O5 0.0367(8) 0.0258(7) 0.0272(7) -0.0086(6) -0.0109(6) 0.0055(6) O1' 0.0136(6) 0.0157(6) 0.0201(6) 0.0031(5) -0.0027(5) 0.0005(4) N1 0.0128(7) 0.0141(7) 0.0188(7) 0.0005(6) -0.0015(6) 0.0008(5) N2 0.0153(7) 0.0141(7) 0.0179(7) -0.0014(5) -0.0021(6) 0.0002(6) C1 0.0189(9) 0.0144(8) 0.0105(8) 0.0012(6) -0.0020(7) -0.0014(6) C1' 0.0163(9) 0.0207(9) 0.0408(11) 0.0081(8) -0.0049(9) 0.0028(7) C2 0.0177(9) 0.0132(8) 0.0151(8) -0.0006(6) 0.0012(7) -0.0003(6) C3 0.0124(8) 0.0136(8) 0.0185(8) -0.0012(6) -0.0002(7) -0.0004(6) C4 0.0133(8) 0.0136(7) 0.0173(8) 0.0010(6) -0.0045(7) 0.0003(6) C5 0.0153(8) 0.0135(8) 0.0124(8) -0.0002(6) -0.0046(7) -0.0007(7) C6 0.0159(8) 0.0249(9) 0.0180(9) 0.0048(7) -0.0023(7) -0.0005(7) C7 0.0205(9) 0.0143(8) 0.0183(9) 0.0018(7) 0.0005(7) -0.0041(7) C8 0.0158(8) 0.0163(8) 0.0203(9) 0.0003(7) 0.0048(7) -0.0040(7) C9 0.0154(9) 0.0197(8) 0.0266(9) -0.0027(7) -0.0034(7) 0.0019(7) C10 0.0322(10) 0.0250(9) 0.0271(10) -0.0044(8) -0.0105(9) 0.0078(8) C9' 0.0215(9) 0.0177(8) 0.0234(9) -0.0015(8) -0.0001(7) 0.0038(7) C10' 0.0322(11) 0.0235(9) 0.0233(9) -0.0030(8) -0.0021(8) 0.0089(8) _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 1.419(2) . ? O1 C5 1.4446(19) . ? O2 C2 1.4234(19) . ? O3 C4 1.4302(19) . ? O4 C6 1.426(2) . ? O5 C10 1.426(2) . ? O5 C10' 1.430(2) . ? O1' C1 1.4156(18) . ? O1' C1' 1.433(2) . ? N1 C7 1.462(2) . ? N1 C3 1.4736(19) . ? N2 C8 1.469(2) . ? N2 C9' 1.469(2) . ? N2 C9 1.472(2) . ? C1 C2 1.519(2) . ? C2 C3 1.535(2) . ? C3 C4 1.531(2) . ? C4 C5 1.527(2) . ? C5 C6 1.511(2) . ? C7 C8 1.523(2) . ? C9 C10 1.511(3) . ? C9' C10' 1.513(2) . ? 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 C5 115.12(11) . . ? C10 O5 C10' 109.91(14) . . ? C1 O1' C1' 112.71(12) . . ? C7 N1 C3 113.81(13) . . ? C8 N2 C9' 112.06(13) . . ? C8 N2 C9 108.80(13) . . ? C9' N2 C9 108.86(13) . . ? O1' C1 O1 112.03(13) . . ? O1' C1 C2 107.81(12) . . ? O1 C1 C2 112.09(13) . . ? O2 C2 C1 105.49(13) . . ? O2 C2 C3 111.45(13) . . ? C1 C2 C3 111.66(13) . . ? N1 C3 C4 108.85(13) . . ? N1 C3 C2 113.30(13) . . ? C4 C3 C2 110.08(13) . . ? O3 C4 C5 111.12(13) . . ? O3 C4 C3 111.02(13) . . ? C5 C4 C3 111.17(13) . . ? O1 C5 C6 105.84(12) . . ? O1 C5 C4 109.35(12) . . ? C6 C5 C4 110.96(13) . . ? O4 C6 C5 110.15(13) . . ? N1 C7 C8 111.59(13) . . ? N2 C8 C7 112.87(14) . . ? N2 C9 C10 110.35(15) . . ? O5 C10 C9 112.30(15) . . ? N2 C9' C10' 110.07(14) . . ? O5 C10' C9' 111.36(15) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.185 _refine_diff_density_min -0.199 _refine_diff_density_rms 0.046 # Attachment '6b.cif' data_03045 _database_code_depnum_ccdc_archive 'CCDC 604071' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H19 N O6' _chemical_formula_weight 273.28 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 9.8736(13) _cell_length_b 6.0745(8) _cell_length_c 11.7121(16) _cell_angle_alpha 90.00 _cell_angle_beta 111.941(2) _cell_angle_gamma 90.00 _cell_volume 651.58(15) _cell_formula_units_Z 2 _cell_measurement_temperature 290(2) _cell_measurement_reflns_used 2681 _cell_measurement_theta_min 2.224 _cell_measurement_theta_max 28.487 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.393 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 292 _exptl_absorpt_coefficient_mu 0.112 _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 290(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4786 _diffrn_reflns_av_R_equivalents 0.0320 _diffrn_reflns_av_sigmaI/netI 0.0358 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.87 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2268 _reflns_number_gt 2146 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Absolute configuration could not be determined from the Flack parameter but was dictated by the starting material 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^)+(0.0473P)^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 constrained _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.9(9) _refine_ls_number_reflns 2268 _refine_ls_number_parameters 176 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0365 _refine_ls_R_factor_gt 0.0350 _refine_ls_wR_factor_ref 0.0792 _refine_ls_wR_factor_gt 0.0783 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.026 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.32358(14) 1.0562(2) 0.30475(11) 0.0303(3) Uani 1 1 d . . . H1A H 0.2608 1.1805 0.2708 0.036 Uiso 1 1 d R . . O1 O 0.18620(12) 0.6363(2) 0.51959(9) 0.0372(3) Uani 1 1 d . . . O2 O 0.44703(12) 0.7923(2) 0.51054(11) 0.0405(3) Uani 1 1 d . . . H2 H 0.5051 0.6970 0.5488 0.061 Uiso 1 1 calc R . . O3 O 0.32976(16) 1.2893(2) 0.06977(12) 0.0568(4) Uani 1 1 d . . . O4 O 0.02939(13) 0.93049(19) 0.14643(10) 0.0405(3) Uani 1 1 d . . . H4 H 0.0117 0.9055 0.0735 0.061 Uiso 1 1 calc R . . O5 O 0.13872(11) 0.44037(16) 0.33884(9) 0.0313(3) Uani 1 1 d . . . O6 O 0.00080(17) 0.3576(2) 0.08679(11) 0.0524(4) Uani 1 1 d . . . H6 H 0.0236 0.2340 0.1158 0.079 Uiso 1 1 calc R . . C1 C 0.24719(17) 0.5333(3) 0.44411(14) 0.0309(4) Uani 1 1 d . . . H1 H 0.3112 0.4148 0.4911 0.037 Uiso 1 1 calc R . . C2 C 0.33865(16) 0.6976(3) 0.40787(13) 0.0297(4) Uani 1 1 d . . . H2A H 0.3855 0.6223 0.3583 0.036 Uiso 1 1 calc R . . C3 C 0.24089(16) 0.8787(3) 0.33086(13) 0.0282(3) Uani 1 1 d . . . H3 H 0.1887 0.9417 0.3797 0.034 Uiso 1 1 calc R . . C4 C 0.12755(17) 0.7688(3) 0.21971(14) 0.0294(4) Uani 1 1 d . . . H4A H 0.1765 0.6965 0.1709 0.035 Uiso 1 1 calc R . . C5 C 0.04199(17) 0.5990(3) 0.26012(14) 0.0306(4) Uani 1 1 d . . . H5 H -0.0099 0.6738 0.3058 0.037 Uiso 1 1 calc R . . C6 C -0.06650(19) 0.4732(3) 0.15585(15) 0.0420(4) Uani 1 1 d . . . H6A H -0.1177 0.3696 0.1884 0.050 Uiso 1 1 calc R . . H6B H -0.1379 0.5746 0.1022 0.050 Uiso 1 1 calc R . . C7 C 0.1225(3) 0.4886(4) 0.57738(18) 0.0608(6) Uani 1 1 d . . . H7A H 0.0394 0.4194 0.5164 0.091 Uiso 1 1 calc R . . H7C H 0.0920 0.5672 0.6348 0.091 Uiso 1 1 calc R . . H7B H 0.1927 0.3783 0.6204 0.091 Uiso 1 1 calc R . . C8 C 0.3992(2) 1.0055(3) 0.22180(18) 0.0427(4) Uani 1 1 d . . . H8A H 0.3373 0.9136 0.1549 0.051 Uiso 1 1 calc R . . H8B H 0.4879 0.9241 0.2662 0.051 Uiso 1 1 calc R . . C9 C 0.43599(19) 1.2083(3) 0.17134(15) 0.0381(4) Uani 1 1 d . . . C10 C 0.5513(2) 1.3396(4) 0.20387(19) 0.0554(6) Uani 1 1 d . . . H10 H 0.6382 1.3215 0.2712 0.066 Uiso 1 1 calc R . . C11 C 0.5176(3) 1.5117(4) 0.1173(2) 0.0650(7) Uani 1 1 d . . . H11 H 0.5782 1.6279 0.1156 0.078 Uiso 1 1 calc R . . C12 C 0.3854(4) 1.4767(4) 0.0402(2) 0.0701(7) Uani 1 1 d . . . H12 H 0.3353 1.5672 -0.0262 0.084 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 0.0360(7) 0.0227(7) 0.0343(7) 0.0006(6) 0.0156(6) 0.0006(6) O1 0.0433(6) 0.0394(7) 0.0336(6) -0.0016(5) 0.0198(5) -0.0063(6) O2 0.0329(6) 0.0382(7) 0.0398(7) 0.0051(6) 0.0014(5) -0.0028(5) O3 0.0636(9) 0.0546(9) 0.0465(8) 0.0063(7) 0.0141(7) 0.0023(7) O4 0.0521(7) 0.0265(6) 0.0306(6) 0.0033(5) 0.0012(6) 0.0059(6) O5 0.0354(6) 0.0223(6) 0.0323(6) 0.0024(5) 0.0082(5) 0.0005(5) O6 0.0891(10) 0.0261(6) 0.0322(6) -0.0025(5) 0.0114(7) 0.0015(7) C1 0.0320(8) 0.0287(9) 0.0293(8) 0.0053(7) 0.0082(7) 0.0025(7) C2 0.0278(8) 0.0300(8) 0.0307(8) 0.0017(7) 0.0103(7) 0.0022(7) C3 0.0335(8) 0.0233(8) 0.0297(8) -0.0007(7) 0.0141(7) 0.0007(7) C4 0.0355(8) 0.0219(8) 0.0285(8) 0.0005(7) 0.0093(7) 0.0045(7) C5 0.0322(8) 0.0263(8) 0.0318(8) 0.0000(7) 0.0103(7) 0.0046(7) C6 0.0410(10) 0.0342(10) 0.0415(10) 0.0032(8) 0.0047(8) -0.0046(8) C7 0.0719(14) 0.0654(14) 0.0594(12) 0.0048(12) 0.0412(11) -0.0146(12) C8 0.0545(11) 0.0311(9) 0.0535(11) -0.0022(8) 0.0327(9) -0.0033(9) C9 0.0460(10) 0.0368(9) 0.0376(9) -0.0014(8) 0.0228(8) -0.0018(9) C10 0.0523(12) 0.0547(13) 0.0629(13) 0.0009(11) 0.0256(10) -0.0100(11) C11 0.0919(19) 0.0405(13) 0.0887(17) 0.0035(12) 0.0638(16) -0.0104(12) C12 0.114(2) 0.0481(13) 0.0598(14) 0.0166(12) 0.0462(15) 0.0163(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 N1 C3 1.4527(19) . ? N1 C8 1.462(2) . ? O1 C1 1.3906(18) . ? O1 C7 1.406(2) . ? O2 C2 1.4002(19) . ? O3 C9 1.351(2) . ? O3 C12 1.363(3) . ? O4 C4 1.4208(18) . ? O5 C1 1.4138(18) . ? O5 C5 1.4257(18) . ? O6 C6 1.411(2) . ? C1 C2 1.509(2) . ? C2 C3 1.518(2) . ? C3 C4 1.518(2) . ? C4 C5 1.517(2) . ? C5 C6 1.499(2) . ? C8 C9 1.469(2) . ? C9 C10 1.325(3) . ? C10 C11 1.407(3) . ? C11 C12 1.298(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 C3 N1 C8 116.74(13) . . ? C1 O1 C7 113.36(14) . . ? C9 O3 C12 105.89(18) . . ? C1 O5 C5 113.59(11) . . ? O1 C1 O5 111.54(12) . . ? O1 C1 C2 109.14(13) . . ? O5 C1 C2 110.89(11) . . ? O2 C2 C1 112.07(12) . . ? O2 C2 C3 108.96(13) . . ? C1 C2 C3 109.38(12) . . ? N1 C3 C4 115.98(12) . . ? N1 C3 C2 112.36(12) . . ? C4 C3 C2 107.01(13) . . ? O4 C4 C5 108.96(12) . . ? O4 C4 C3 109.40(12) . . ? C5 C4 C3 110.45(12) . . ? O5 C5 C6 106.52(13) . . ? O5 C5 C4 110.17(12) . . ? C6 C5 C4 113.86(13) . . ? O6 C6 C5 112.01(14) . . ? N1 C8 C9 110.78(14) . . ? C10 C9 O3 109.57(17) . . ? C10 C9 C8 134.79(19) . . ? O3 C9 C8 115.61(16) . . ? C9 C10 C11 107.1(2) . . ? C12 C11 C10 106.5(2) . . ? C11 C12 O3 110.9(2) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.164 _refine_diff_density_min -0.227 _refine_diff_density_rms 0.057