# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2004 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Dr Wai Hung Yuen' _publ_contact_author_address ; Dr Wai Hung Yuen The University of Hong Kong Department of Chemistry Pokfulam Road HONG KONG ; _publ_contact_author_email YUENWH@HKUSUA.HKU.HK _publ_section_title ; Studies related to carba-pyranoses: synthesis of acetylated derivatives of 4-amino-2,4-dideoxy-3-O-(beta-D-glucopyranosyl)-beta-L-(and beta-D-) altrocarba-pyranose from a D-glucose template ; _publ_requested_category FO loop_ _publ_author_name 'Wai Hung Yuen.' 'Robin G. Pritchard' 'R. Stoodley' data_simon _database_code_depnum_ccdc_archive 'CCDC 245217' _audit_creation_date 2004-07-20T00:21:10-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.2 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C22 H31 N1 O15' _chemical_formula_sum 'C22 H31 N O15' _chemical_formula_weight 549.48 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration rm #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21' _symmetry_space_group_name_Hall 'P 2yb' _symmetry_Int_Tables_number 4 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 5.773(1) _cell_length_b 22.641(3) _cell_length_c 10.86(2) _cell_angle_alpha 90 _cell_angle_beta 105.380(2) _cell_angle_gamma 90 _cell_volume 1368.6(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 1.5 _cell_measurement_theta_max 25 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_diffrn 1.333 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 580 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.114 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details ; North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351 Number of psi-scan sets used was 3 Theta correction was applied. Averaged transmission function was used. No Fourier smoothing was applied. ; _exptl_absorpt_correction_T_min 0.9666 _exptl_absorpt_correction_T_max 0.9776 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'scintillation LiI' _diffrn_detector_dtime 1.195 _diffrn_orient_matrix_type ; x-axis points to radiation source the matrix is specified in reciprocal space ; _diffrn_orient_matrix_ub_11 0.020001 _diffrn_orient_matrix_ub_12 -0.00335 _diffrn_orient_matrix_ub_13 0.094061 _diffrn_orient_matrix_ub_21 -0.166928 _diffrn_orient_matrix_ub_22 -0.015986 _diffrn_orient_matrix_ub_23 -0.016465 _diffrn_orient_matrix_ub_31 0.063356 _diffrn_orient_matrix_ub_32 -0.041036 _diffrn_orient_matrix_ub_33 -0.001245 _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_measurement_device_type 'Enraf Nonius CAD4' _diffrn_measurement_method 'non-profiled omega/2theta scans' _diffrn_standards_number 3 _diffrn_standards_interval_time 60 _diffrn_standards_decay_% -5 _diffrn_standards_decay_corr_max 1.017 _diffrn_standards_decay_corr_min 0.919 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l -1 -1 1 -1 -2 1 1 2 -1 _diffrn_reflns_av_R_equivalents 0.0482 _diffrn_reflns_av_unetI/netI 0.1336 _diffrn_reflns_number 4176 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.33 _diffrn_reflns_theta_max 24.97 _diffrn_reflns_theta_full 24.97 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _reflns_number_total 2451 _reflns_number_gt 1085 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'CAD4 Express (Enraf Nonius, 1994)' _computing_cell_refinement 'CAD4 Express (Enraf Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0420P)^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_number_reflns 2451 _refine_ls_number_parameters 343 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1852 _refine_ls_R_factor_gt 0.0617 _refine_ls_wR_factor_ref 0.1141 _refine_ls_wR_factor_gt 0.0844 _refine_ls_goodness_of_fit_ref 1.009 _refine_ls_restrained_S_all 1.009 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 1(2) _refine_diff_density_max 0.176 _refine_diff_density_min -0.176 _refine_diff_density_rms 0.042 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 C1' C 0.3903(15) 0.2891(4) 0.2544(8) 0.051(2) Uani 1 1 d . . . H1' H 0.2662 0.3037 0.2933 0.061 Uiso 1 1 calc R . . C1 C 0.2853(15) 0.1071(3) 0.4603(7) 0.049(2) Uani 1 1 d . . . H1 H 0.1222 0.1083 0.4035 0.058 Uiso 1 1 calc R . . C2' C 0.5719(15) 0.3368(3) 0.2559(7) 0.047(2) Uani 1 1 d . . . H2' H 0.7108 0.3201 0.2322 0.056 Uiso 1 1 calc R . . C2 C 0.4449(15) 0.1446(3) 0.4002(7) 0.047(2) Uani 1 1 d . . . H2 H 0.6089 0.1439 0.4562 0.056 Uiso 1 1 calc R . . C3' C 0.4710(15) 0.3872(3) 0.1691(7) 0.042(2) Uani 1 1 d . . . H3' H 0.3649 0.4104 0.2074 0.051 Uiso 1 1 calc R . . C3 C 0.3581(15) 0.2079(3) 0.3849(7) 0.047(2) Uani 1 1 d . . . H3 H 0.1926 0.2084 0.3308 0.056 Uiso 1 1 calc R . . C4 C 0.3613(16) 0.2336(4) 0.5123(8) 0.058(2) Uani 1 1 d . . . H4A H 0.3055 0.2741 0.5018 0.07 Uiso 1 1 calc R . . H4B H 0.5244 0.2335 0.5669 0.07 Uiso 1 1 calc R . . C4' C 0.3271(15) 0.3648(3) 0.0388(7) 0.048(2) Uani 1 1 d . . . H4' H 0.4355 0.3483 -0.0082 0.058 Uiso 1 1 calc R . . C5 C 0.2022(18) 0.1980(4) 0.5739(8) 0.067(3) Uani 1 1 d . . . H5A H 0.0373 0.2001 0.5193 0.08 Uiso 1 1 calc R . . C5' C 0.1491(17) 0.3187(3) 0.0544(8) 0.054(2) Uani 1 1 d . . . H5' H 0.0415 0.3356 0.1014 0.065 Uiso 1 1 calc R . . C6 C 0.2771(16) 0.1343(3) 0.5887(7) 0.059(3) Uani 1 1 d . . . H6A H 0.1647 0.1123 0.6233 0.071 Uiso 1 1 calc R . . H6B H 0.4347 0.1313 0.6486 0.071 Uiso 1 1 calc R . . C6' C 0.0023(18) 0.2938(5) -0.0711(9) 0.084(3) Uani 1 1 d . . . H61' H -0.0803 0.3251 -0.1264 0.1 Uiso 1 1 calc R . . H62' H 0.1046 0.2728 -0.1143 0.1 Uiso 1 1 calc R . . C7 C 0.3582(19) 0.0445(4) 0.4788(7) 0.051(2) Uani 1 1 d . . . C7' C 0.874(2) 0.3590(4) 0.4496(10) 0.065(3) Uani 1 1 d . . . C8 C 0.6788(19) -0.0240(4) 0.5137(10) 0.093(3) Uani 1 1 d . . . H8A H 0.8481 -0.0245 0.5208 0.139 Uiso 1 1 calc R . . H8B H 0.597 -0.0488 0.444 0.139 Uiso 1 1 calc R . . H8C H 0.6505 -0.0384 0.5916 0.139 Uiso 1 1 calc R . . C8' C 0.9153(18) 0.3659(4) 0.5901(8) 0.079(3) Uani 1 1 d . . . H81' H 0.7634 0.3677 0.6103 0.118 Uiso 1 1 calc R . . H82' H 1.0033 0.4016 0.6175 0.118 Uiso 1 1 calc R . . H83' H 1.0055 0.3328 0.6329 0.118 Uiso 1 1 calc R . . C9' C 0.6415(19) 0.4834(4) 0.1663(8) 0.060(3) Uani 1 1 d . . . C10' C 0.8535(17) 0.5147(4) 0.1395(10) 0.085(3) Uani 1 1 d . . . H10A H 0.9612 0.4862 0.1197 0.128 Uiso 1 1 calc R . . H10B H 0.9361 0.5369 0.2135 0.128 Uiso 1 1 calc R . . H10C H 0.7983 0.541 0.0684 0.128 Uiso 1 1 calc R . . C11' C 0.271(2) 0.4395(5) -0.1269(10) 0.079(4) Uani 1 1 d . . . C12' C 0.133(3) 0.4926(4) -0.1715(9) 0.123(5) Uani 1 1 d . . . H12A H 0.0109 0.4972 -0.1268 0.185 Uiso 1 1 calc R . . H12B H 0.0582 0.4893 -0.2615 0.185 Uiso 1 1 calc R . . H12C H 0.2371 0.5263 -0.1558 0.185 Uiso 1 1 calc R . . C13' C -0.199(2) 0.2005(5) -0.0942(9) 0.077(3) Uani 1 1 d . . . C14' C -0.3600(19) 0.1630(5) -0.0398(9) 0.102(4) Uani 1 1 d . . . H14A H -0.4028 0.184 0.0277 0.154 Uiso 1 1 calc R . . H14B H -0.2779 0.1271 -0.0066 0.154 Uiso 1 1 calc R . . H14C H -0.5027 0.1536 -0.1056 0.154 Uiso 1 1 calc R . . N1 N 0.449(2) 0.1216(3) 0.2722(9) 0.077(3) Uani 1 1 d . . . O2' O 0.6439(11) 0.3574(2) 0.3850(5) 0.0520(15) Uani 1 1 d . . . O2A O 0.2655(19) 0.1098(4) 0.1961(7) 0.125(4) Uani 1 1 d . . . O2B O 0.6516(16) 0.1167(4) 0.2562(7) 0.116(3) Uani 1 1 d . . . O3' O 0.6655(10) 0.4242(2) 0.1549(4) 0.0532(15) Uani 1 1 d . . . O3 O 0.5065(10) 0.2406(2) 0.3226(5) 0.0552(15) Uani 1 1 d . . . O4' O 0.1967(11) 0.4141(2) -0.0298(5) 0.0653(17) Uani 1 1 d . . . O5' O 0.2843(10) 0.2718(2) 0.1266(5) 0.0525(16) Uani 1 1 d . . . O5 O 0.2094(14) 0.2262(2) 0.6929(6) 0.104(3) Uani 1 1 d . . . H5 H 0.2553 0.2025 0.7514 0.155 Uiso 1 1 calc R . . O6' O -0.1704(11) 0.2534(3) -0.0388(5) 0.075(2) Uani 1 1 d . . . O7' O 1.0345(13) 0.3552(4) 0.3984(7) 0.103(2) Uani 1 1 d . . . O7A O 0.2255(12) 0.0054(3) 0.4879(7) 0.088(2) Uani 1 1 d . . . O7B O 0.5884(12) 0.0364(2) 0.4906(6) 0.0663(17) Uani 1 1 d . . . O9' O 0.4776(13) 0.5067(3) 0.1924(7) 0.095(3) Uani 1 1 d . . . O11' O 0.4393(17) 0.4202(4) -0.1596(7) 0.118(3) Uani 1 1 d . . . O13' O -0.1160(16) 0.1878(3) -0.1789(7) 0.129(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1' 0.060(6) 0.048(6) 0.054(6) 0.009(5) 0.031(5) -0.004(5) C1 0.047(6) 0.041(5) 0.057(6) 0.011(4) 0.013(5) -0.002(5) C2' 0.056(6) 0.043(5) 0.044(6) -0.008(4) 0.018(5) 0.007(5) C2 0.061(6) 0.036(5) 0.042(5) 0.002(4) 0.012(5) -0.001(5) C3' 0.044(5) 0.037(5) 0.047(5) 0.010(4) 0.015(4) -0.009(4) C3 0.052(6) 0.052(6) 0.048(5) 0.012(4) 0.032(5) 0.002(5) C4 0.073(7) 0.048(5) 0.063(6) 0.007(5) 0.035(5) 0.011(5) C4' 0.064(6) 0.037(5) 0.050(5) 0.009(4) 0.027(5) 0.008(5) C5 0.100(8) 0.056(6) 0.058(6) -0.008(5) 0.048(6) -0.005(6) C5' 0.080(7) 0.040(5) 0.050(6) 0.011(5) 0.028(5) -0.001(5) C6 0.090(7) 0.043(5) 0.055(6) 0.004(4) 0.039(5) -0.014(5) C6' 0.116(9) 0.093(7) 0.047(6) -0.009(6) 0.031(6) -0.046(8) C7 0.066(8) 0.038(6) 0.052(6) 0.002(4) 0.024(6) -0.009(6) C7' 0.080(8) 0.044(6) 0.074(7) -0.005(5) 0.023(7) 0.024(6) C8 0.095(8) 0.055(7) 0.148(10) 0.029(6) 0.067(7) 0.026(6) C8' 0.101(8) 0.082(7) 0.046(6) -0.008(5) 0.007(5) 0.007(6) C9' 0.067(8) 0.046(7) 0.069(6) 0.006(5) 0.022(6) -0.004(6) C10' 0.084(8) 0.054(6) 0.125(9) 0.009(6) 0.040(7) -0.011(6) C11' 0.098(10) 0.073(9) 0.054(7) 0.009(6) 0.001(7) -0.018(7) C12' 0.230(15) 0.049(7) 0.077(8) 0.018(6) 0.016(8) 0.001(9) C13' 0.104(8) 0.080(8) 0.044(6) 0.004(6) 0.016(6) -0.018(7) C14' 0.125(10) 0.097(8) 0.096(8) 0.000(7) 0.048(7) -0.053(8) N1 0.135(10) 0.043(5) 0.075(7) -0.004(4) 0.066(7) 0.010(6) O2' 0.052(4) 0.053(4) 0.052(4) 0.003(3) 0.017(3) 0.013(3) O2A 0.165(9) 0.145(8) 0.065(5) -0.043(5) 0.031(5) -0.058(7) O2B 0.160(8) 0.112(6) 0.107(6) 0.033(5) 0.091(6) 0.061(6) O3' 0.063(4) 0.038(3) 0.064(4) 0.006(3) 0.026(3) 0.001(3) O3 0.067(4) 0.044(3) 0.068(4) 0.020(3) 0.042(3) 0.006(3) O4' 0.087(5) 0.059(4) 0.051(4) 0.016(3) 0.019(3) 0.003(4) O5' 0.076(4) 0.044(3) 0.044(4) -0.004(3) 0.027(3) -0.010(3) O5 0.194(8) 0.058(4) 0.087(5) -0.001(4) 0.087(5) 0.005(5) O6' 0.089(5) 0.091(5) 0.048(4) -0.002(4) 0.023(4) -0.031(5) O7' 0.067(5) 0.146(7) 0.100(5) -0.022(5) 0.025(5) 0.021(5) O7A 0.057(5) 0.061(4) 0.147(7) 0.014(4) 0.030(5) -0.007(4) O7B 0.058(5) 0.045(4) 0.104(5) 0.027(3) 0.036(4) 0.010(3) O9' 0.090(6) 0.055(4) 0.161(8) -0.003(4) 0.073(5) 0.004(5) O11' 0.158(8) 0.124(7) 0.090(6) 0.051(5) 0.062(6) 0.003(7) O13' 0.199(9) 0.105(6) 0.117(6) -0.048(5) 0.099(6) -0.066(6) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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' O3 1.393(9) . ? C1' O5' 1.416(8) . ? C1' C2' 1.502(10) . ? C1' H1' 0.98 . ? C1 C7 1.476(11) . ? C1 C2 1.521(10) . ? C1 C6 1.536(9) . ? C1 H1 0.98 . ? C2' O2' 1.431(8) . ? C2' C3' 1.496(10) . ? C2' H2' 0.98 . ? C2 N1 1.491(10) . ? C2 C3 1.512(9) . ? C2 H2 0.98 . ? C3' O3' 1.442(8) . ? C3' C4' 1.526(10) . ? C3' H3' 0.98 . ? C3 O3 1.432(8) . ? C3 C4 1.497(10) . ? C3 H3 0.98 . ? C4 C5 1.504(10) . ? C4 H4A 0.97 . ? C4 H4B 0.97 . ? C4' O4' 1.439(9) . ? C4' C5' 1.505(10) . ? C4' H4' 0.98 . ? C5 O5 1.432(9) . ? C5 C6 1.503(10) . ? C5 H5A 0.98 . ? C5' O5' 1.424(8) . ? C5' C6' 1.510(10) . ? C5' H5' 0.98 . ? C6 H6A 0.97 . ? C6 H6B 0.97 . ? C6' O6' 1.461(9) . ? C6' H61' 0.97 . ? C6' H62' 0.97 . ? C7 O7A 1.193(9) . ? C7 O7B 1.314(9) . ? C7' O7' 1.202(10) . ? C7' O2' 1.330(11) . ? C7' C8' 1.489(11) . ? C8 O7B 1.462(9) . ? C8 H8A 0.96 . ? C8 H8B 0.96 . ? C8 H8C 0.96 . ? C8' H81' 0.96 . ? C8' H82' 0.96 . ? C8' H83' 0.96 . ? C9' O9' 1.181(10) . ? C9' O3' 1.356(9) . ? C9' C10' 1.508(11) . ? C10' H10A 0.96 . ? C10' H10B 0.96 . ? C10' H10C 0.96 . ? C11' O11' 1.200(11) . ? C11' O4' 1.368(11) . ? C11' C12' 1.453(13) . ? C12' H12A 0.96 . ? C12' H12B 0.96 . ? C12' H12C 0.96 . ? C13' O13' 1.180(10) . ? C13' O6' 1.333(11) . ? C13' C14' 1.490(12) . ? C14' H14A 0.96 . ? C14' H14B 0.96 . ? C14' H14C 0.96 . ? N1 O2A 1.190(10) . ? N1 O2B 1.230(10) . ? O5 H5 0.82 . ? 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 C1' O5' 108.9(7) . . ? O3 C1' C2' 108.9(6) . . ? O5' C1' C2' 109.2(6) . . ? O3 C1' H1' 109.9 . . ? O5' C1' H1' 109.9 . . ? C2' C1' H1' 109.9 . . ? C7 C1 C2 114.2(7) . . ? C7 C1 C6 109.7(6) . . ? C2 C1 C6 109.5(6) . . ? C7 C1 H1 107.7 . . ? C2 C1 H1 107.7 . . ? C6 C1 H1 107.7 . . ? O2' C2' C3' 109.4(6) . . ? O2' C2' C1' 105.4(7) . . ? C3' C2' C1' 112.8(6) . . ? O2' C2' H2' 109.7 . . ? C3' C2' H2' 109.7 . . ? C1' C2' H2' 109.7 . . ? N1 C2 C3 108.4(6) . . ? N1 C2 C1 111.5(7) . . ? C3 C2 C1 110.8(6) . . ? N1 C2 H2 108.7 . . ? C3 C2 H2 108.7 . . ? C1 C2 H2 108.7 . . ? O3' C3' C2' 109.1(6) . . ? O3' C3' C4' 110.0(6) . . ? C2' C3' C4' 110.8(6) . . ? O3' C3' H3' 109 . . ? C2' C3' H3' 109 . . ? C4' C3' H3' 109 . . ? O3 C3 C4 111.9(7) . . ? O3 C3 C2 108.7(6) . . ? C4 C3 C2 110.1(6) . . ? O3 C3 H3 108.7 . . ? C4 C3 H3 108.7 . . ? C2 C3 H3 108.7 . . ? C3 C4 C5 110.1(7) . . ? C3 C4 H4A 109.6 . . ? C5 C4 H4A 109.6 . . ? C3 C4 H4B 109.6 . . ? C5 C4 H4B 109.6 . . ? H4A C4 H4B 108.2 . . ? O4' C4' C5' 108.5(7) . . ? O4' C4' C3' 107.6(6) . . ? C5' C4' C3' 110.2(6) . . ? O4' C4' H4' 110.2 . . ? C5' C4' H4' 110.2 . . ? C3' C4' H4' 110.2 . . ? O5 C5 C6 113.1(7) . . ? O5 C5 C4 106.8(7) . . ? C6 C5 C4 111.6(7) . . ? O5 C5 H5A 108.4 . . ? C6 C5 H5A 108.4 . . ? C4 C5 H5A 108.4 . . ? O5' C5' C4' 106.7(7) . . ? O5' C5' C6' 108.2(7) . . ? C4' C5' C6' 113.2(7) . . ? O5' C5' H5' 109.5 . . ? C4' C5' H5' 109.5 . . ? C6' C5' H5' 109.5 . . ? C5 C6 C1 111.4(7) . . ? C5 C6 H6A 109.4 . . ? C1 C6 H6A 109.4 . . ? C5 C6 H6B 109.4 . . ? C1 C6 H6B 109.4 . . ? H6A C6 H6B 108 . . ? O6' C6' C5' 105.8(7) . . ? O6' C6' H61' 110.6 . . ? C5' C6' H61' 110.6 . . ? O6' C6' H62' 110.6 . . ? C5' C6' H62' 110.6 . . ? H61' C6' H62' 108.7 . . ? O7A C7 O7B 122.9(8) . . ? O7A C7 C1 124.0(10) . . ? O7B C7 C1 113.1(8) . . ? O7' C7' O2' 122.6(9) . . ? O7' C7' C8' 123.3(10) . . ? O2' C7' C8' 114.1(10) . . ? O7B C8 H8A 109.5 . . ? O7B C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? O7B C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C7' C8' H81' 109.5 . . ? C7' C8' H82' 109.5 . . ? H81' C8' H82' 109.5 . . ? C7' C8' H83' 109.5 . . ? H81' C8' H83' 109.5 . . ? H82' C8' H83' 109.5 . . ? O9' C9' O3' 124.8(9) . . ? O9' C9' C10' 125.3(9) . . ? O3' C9' C10' 109.8(9) . . ? C9' C10' H10A 109.5 . . ? C9' C10' H10B 109.5 . . ? H10A C10' H10B 109.5 . . ? C9' C10' H10C 109.5 . . ? H10A C10' H10C 109.5 . . ? H10B C10' H10C 109.5 . . ? O11' C11' O4' 121.2(11) . . ? O11' C11' C12' 128.3(12) . . ? O4' C11' C12' 110.3(11) . . ? C11' C12' H12A 109.5 . . ? C11' C12' H12B 109.5 . . ? H12A C12' H12B 109.5 . . ? C11' C12' H12C 109.5 . . ? H12A C12' H12C 109.5 . . ? H12B C12' H12C 109.5 . . ? O13' C13' O6' 122.9(10) . . ? O13' C13' C14' 126.5(11) . . ? O6' C13' C14' 110.5(9) . . ? C13' C14' H14A 109.5 . . ? C13' C14' H14B 109.5 . . ? H14A C14' H14B 109.5 . . ? C13' C14' H14C 109.5 . . ? H14A C14' H14C 109.5 . . ? H14B C14' H14C 109.5 . . ? O2A N1 O2B 125.9(10) . . ? O2A N1 C2 119.6(10) . . ? O2B N1 C2 114.5(10) . . ? C7' O2' C2' 121.0(7) . . ? C9' O3' C3' 117.6(7) . . ? C1' O3 C3 113.3(6) . . ? C11' O4' C4' 119.8(8) . . ? C1' O5' C5' 111.4(6) . . ? C5 O5 H5 109.5 . . ? C13' O6' C6' 117.7(8) . . ? C7 O7B C8 117.0(7) . . ? 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 C1' C2' O2' -69.2(7) . . . . ? O5' C1' C2' O2' 171.9(6) . . . . ? O3 C1' C2' C3' 171.5(6) . . . . ? O5' C1' C2' C3' 52.7(8) . . . . ? C7 C1 C2 N1 59.2(9) . . . . ? C6 C1 C2 N1 -177.3(7) . . . . ? C7 C1 C2 C3 -180.0(7) . . . . ? C6 C1 C2 C3 -56.5(9) . . . . ? O2' C2' C3' O3' 75.4(8) . . . . ? C1' C2' C3' O3' -167.7(6) . . . . ? O2' C2' C3' C4' -163.4(6) . . . . ? C1' C2' C3' C4' -46.5(8) . . . . ? N1 C2 C3 O3 -54.6(9) . . . . ? C1 C2 C3 O3 -177.3(6) . . . . ? N1 C2 C3 C4 -177.5(8) . . . . ? C1 C2 C3 C4 59.8(8) . . . . ? O3 C3 C4 C5 179.7(6) . . . . ? C2 C3 C4 C5 -59.3(9) . . . . ? O3' C3' C4' O4' -70.8(7) . . . . ? C2' C3' C4' O4' 168.5(6) . . . . ? O3' C3' C4' C5' 171.1(7) . . . . ? C2' C3' C4' C5' 50.4(9) . . . . ? C3 C4 C5 O5 -178.4(7) . . . . ? C3 C4 C5 C6 57.6(10) . . . . ? O4' C4' C5' O5' -177.8(6) . . . . ? C3' C4' C5' O5' -60.2(8) . . . . ? O4' C4' C5' C6' 63.2(9) . . . . ? C3' C4' C5' C6' -179.2(7) . . . . ? O5 C5 C6 C1 -175.7(7) . . . . ? C4 C5 C6 C1 -55.3(9) . . . . ? C7 C1 C6 C5 -179.7(8) . . . . ? C2 C1 C6 C5 54.2(9) . . . . ? O5' C5' C6' O6' 65.9(9) . . . . ? C4' C5' C6' O6' -176.1(7) . . . . ? C2 C1 C7 O7A -157.0(8) . . . . ? C6 C1 C7 O7A 79.6(10) . . . . ? C2 C1 C7 O7B 26.2(10) . . . . ? C6 C1 C7 O7B -97.2(8) . . . . ? C3 C2 N1 O2A -73.9(11) . . . . ? C1 C2 N1 O2A 48.3(11) . . . . ? C3 C2 N1 O2B 106.0(9) . . . . ? C1 C2 N1 O2B -131.8(8) . . . . ? O7' C7' O2' C2' 15.4(14) . . . . ? C8' C7' O2' C2' -164.5(7) . . . . ? C3' C2' O2' C7' -112.4(8) . . . . ? C1' C2' O2' C7' 126.1(8) . . . . ? O9' C9' O3' C3' 3.4(13) . . . . ? C10' C9' O3' C3' -176.1(7) . . . . ? C2' C3' O3' C9' -133.5(7) . . . . ? C4' C3' O3' C9' 104.7(8) . . . . ? O5' C1' O3 C3 -92.3(7) . . . . ? C2' C1' O3 C3 148.7(6) . . . . ? C4 C3 O3 C1' -84.9(8) . . . . ? C2 C3 O3 C1' 153.3(6) . . . . ? O11' C11' O4' C4' 2.8(14) . . . . ? C12' C11' O4' C4' -173.0(8) . . . . ? C5' C4' O4' C11' -135.4(8) . . . . ? C3' C4' O4' C11' 105.4(7) . . . . ? O3 C1' O5' C5' 176.1(6) . . . . ? C2' C1' O5' C5' -65.1(8) . . . . ? C4' C5' O5' C1' 69.2(7) . . . . ? C6' C5' O5' C1' -168.7(6) . . . . ? O13' C13' O6' C6' -9.9(15) . . . . ? C14' C13' O6' C6' 173.7(8) . . . . ? C5' C6' O6' C13' -133.9(8) . . . . ? O7A C7 O7B C8 1.1(13) . . . . ? C1 C7 O7B C8 178.0(7) . . . . ? data_tom96y _database_code_depnum_ccdc_archive 'CCDC 245218' _audit_creation_date 2004-07-20T01:14:12-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.2 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C4 H5 N1 O4' _chemical_formula_sum 'C4 H5 N O4' _chemical_formula_weight 131.09 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 5.356(2) _cell_length_b 6.688(2) _cell_length_c 16.787(7) _cell_angle_alpha 90 _cell_angle_beta 96.99(3) _cell_angle_gamma 90 _cell_volume 596.9(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 9.2 _cell_measurement_theta_max 15.2 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.15 _exptl_crystal_density_diffrn 1.459 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 272 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.133 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9611 _exptl_absorpt_correction_T_max 0.9803 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'scintillation LiI' _diffrn_detector_dtime 1.195 _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_measurement_device_type 'Enraf Nonius CAD4' _diffrn_measurement_method 'non-profiled omega/2theta scans' _diffrn_standards_number 3 _diffrn_standards_interval_time 60 _diffrn_standards_decay_% -3 _diffrn_standards_decay_corr_max 1.01 _diffrn_standards_decay_corr_min 0.943 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l -3 0 1 0 2 1 0 1 3 _diffrn_reflns_av_R_equivalents 0.0227 _diffrn_reflns_av_unetI/netI 0.0329 _diffrn_reflns_number 987 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.44 _diffrn_reflns_theta_max 24.99 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.836 _diffrn_measured_fraction_theta_max 0.836 _reflns_number_total 878 _reflns_number_gt 621 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'CAD4 Express (Enraf Nonius, 1994)' _computing_cell_refinement 'CAD4 Express (Enraf Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0598P)^2^+0.2347P] 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_number_reflns 878 _refine_ls_number_parameters 90 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0829 _refine_ls_R_factor_gt 0.0534 _refine_ls_wR_factor_ref 0.1404 _refine_ls_wR_factor_gt 0.1216 _refine_ls_goodness_of_fit_ref 1.146 _refine_ls_restrained_S_all 1.146 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.19 _refine_diff_density_min -0.141 _refine_diff_density_rms 0.042 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 0.1496(4) 0.1599(3) 0.42302(12) 0.0613(7) Uani 1 1 d . . . O2 O 0.5209(6) 0.2451(4) 0.48988(14) 0.0693(8) Uani 1 1 d . . . O3 O -0.1138(5) 0.4165(4) 0.67225(13) 0.0713(8) Uani 1 1 d . . . O4 O 0.2231(5) 0.5610(4) 0.72791(14) 0.0836(9) Uani 1 1 d . . . N1 N 0.1090(6) 0.4578(4) 0.67540(14) 0.0548(8) Uani 1 1 d . . . C1 C 0.2973(8) 0.2320(5) 0.48607(17) 0.0488(9) Uani 1 1 d . . . C2 C 0.1457(8) 0.2924(5) 0.54976(17) 0.0500(9) Uani 1 1 d . . . C3 C 0.2531(7) 0.3869(5) 0.61290(17) 0.0513(9) Uani 1 1 d . . . C4 C 0.2745(7) 0.0982(6) 0.35490(18) 0.0714(11) Uani 1 1 d . . . H4A H 0.1517 0.0489 0.3131 0.107 Uiso 0.5 1 calc PR . . H4B H 0.3936 -0.0056 0.3713 0.107 Uiso 0.5 1 calc PR . . H4C H 0.3606 0.2105 0.3353 0.107 Uiso 0.5 1 calc PR . . H4D H 0.4522 0.1203 0.3667 0.107 Uiso 0.5 1 calc PR . . H4E H 0.2103 0.1748 0.3085 0.107 Uiso 0.5 1 calc PR . . H4F H 0.2433 -0.0413 0.3444 0.107 Uiso 0.5 1 calc PR . . H2 H -0.024(7) 0.265(5) 0.5433(17) 0.050(10) Uiso 1 1 d . . . H3 H 0.428(7) 0.410(5) 0.6230(19) 0.061(11) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0642(17) 0.0760(15) 0.0428(11) -0.0071(11) 0.0037(10) -0.0026(13) O2 0.0545(19) 0.0899(19) 0.0640(15) -0.0133(13) 0.0089(11) -0.0033(15) O3 0.0632(19) 0.0938(19) 0.0588(14) -0.0059(12) 0.0150(12) -0.0065(16) O4 0.095(2) 0.094(2) 0.0582(15) -0.0282(14) -0.0030(14) -0.0051(16) N1 0.067(2) 0.0567(17) 0.0402(14) 0.0006(12) 0.0023(13) 0.0016(17) C1 0.055(3) 0.0475(18) 0.0436(16) 0.0034(13) 0.0043(15) -0.0032(18) C2 0.054(3) 0.0509(19) 0.0448(17) 0.0077(14) 0.0038(15) -0.0060(18) C3 0.050(3) 0.057(2) 0.0466(17) -0.0013(15) 0.0045(15) -0.0026(18) C4 0.091(3) 0.076(2) 0.0485(18) -0.0101(17) 0.0122(18) 0.005(2) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 1.332(4) . ? O1 C4 1.453(4) . ? O2 C1 1.195(4) . ? O3 N1 1.220(3) . ? O4 N1 1.223(3) . ? N1 C3 1.455(4) . ? C1 C2 1.475(5) . ? C2 C3 1.306(4) . ? C2 H2 0.92(3) . ? C3 H3 0.94(3) . ? C4 H4A 0.96 . ? C4 H4B 0.96 . ? C4 H4C 0.96 . ? C4 H4D 0.96 . ? C4 H4E 0.96 . ? C4 H4F 0.96 . ? 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 C4 116.3(3) . . ? O3 N1 O4 124.0(3) . . ? O3 N1 C3 119.8(3) . . ? O4 N1 C3 116.2(3) . . ? O2 C1 O1 124.3(3) . . ? O2 C1 C2 125.3(3) . . ? O1 C1 C2 110.4(3) . . ? C3 C2 C1 119.6(4) . . ? C3 C2 H2 121.5(19) . . ? C1 C2 H2 118.9(19) . . ? C2 C3 N1 121.6(4) . . ? C2 C3 H3 124(2) . . ? N1 C3 H3 114.7(19) . . ? O1 C4 H4A 109.5 . . ? O1 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? O1 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? O1 C4 H4D 109.5 . . ? H4A C4 H4D 141.1 . . ? H4B C4 H4D 56.3 . . ? H4C C4 H4D 56.3 . . ? O1 C4 H4E 109.5 . . ? H4A C4 H4E 56.3 . . ? H4B C4 H4E 141.1 . . ? H4C C4 H4E 56.3 . . ? H4D C4 H4E 109.5 . . ? O1 C4 H4F 109.5 . . ? H4A C4 H4F 56.3 . . ? H4B C4 H4F 56.3 . . ? H4C C4 H4F 141.1 . . ? H4D C4 H4F 109.5 . . ? H4E C4 H4F 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 C4 O1 C1 O2 -1.3(5) . . . . ? C4 O1 C1 C2 178.8(3) . . . . ? O2 C1 C2 C3 7.5(5) . . . . ? O1 C1 C2 C3 -172.6(3) . . . . ? C1 C2 C3 N1 177.0(3) . . . . ? O3 N1 C3 C2 5.3(5) . . . . ? O4 N1 C3 C2 -173.2(3) . . . . ?