Electronic Supplementary Material for CrystEngComm This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Lucia Maini' _publ_contact_author_address ; Dipartimento di Chimica Universita delgi studi di Bologna via Selmi 2 Bologna 40126 ITALY ; _publ_contact_author_email LUCIAMAINI@UNIBO.IT _publ_section_title ; Gas-Solid Reactions between the Different Polymorphic Modifications of Barbituric Acid and Amines ; loop_ _publ_author_name 'Lucia Maini' 'Dario Braga' M.Cadoni F.Grepioni 'Katia Rubini' # Attachment '1b.cif' data_piccola _database_code_depnum_ccdc_archive 'CCDC 294126' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C5 H9 N3 O3' _chemical_formula_weight 159.15 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.544(3) _cell_length_b 9.588(3) _cell_length_c 9.915(3) _cell_angle_alpha 86.554(5) _cell_angle_beta 68.376(5) _cell_angle_gamma 63.175(5) _cell_volume 746.5(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour 'light pink' _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.416 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 336 _exptl_absorpt_coefficient_mu 0.118 _exptl_absorpt_correction_type sadabs _exptl_absorpt_correction_T_min 0.7572 _exptl_absorpt_correction_T_max 1.000 _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 'area detector' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8594 _diffrn_reflns_av_R_equivalents 0.0534 _diffrn_reflns_av_sigmaI/netI 0.0933 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.23 _diffrn_reflns_theta_max 28.55 _reflns_number_total 3449 _reflns_number_gt 1625 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'bruker apex2' _computing_cell_refinement Apex2 _computing_data_reduction saint _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics schakal _computing_publication_material wingX _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^)+(0.1550P)^2^+1.7662P] 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_number_reflns 3449 _refine_ls_number_parameters 241 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1752 _refine_ls_R_factor_gt 0.0917 _refine_ls_wR_factor_ref 0.3479 _refine_ls_wR_factor_gt 0.3044 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _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 C1 C 0.4756(7) 0.2986(6) 0.9863(5) 0.0350(12) Uani 1 1 d . . . C2 C 0.4789(7) 0.3472(6) 0.7409(6) 0.0341(12) Uani 1 1 d . . . C3 C 0.6694(7) 0.0920(6) 0.7839(6) 0.0348(12) Uani 1 1 d . . . C4 C 0.5999(7) 0.1452(6) 0.9321(6) 0.0371(13) Uani 1 1 d . . . H4 H 0.6374 0.0766 0.9959 0.045 Uiso 1 1 calc R . . N1 N 0.4172(6) 0.3933(5) 0.8874(5) 0.0377(11) Uani 1 1 d . . . N2 N 0.6024(6) 0.1972(5) 0.6945(5) 0.0380(11) Uani 1 1 d . . . O1 O 0.4083(5) 0.3640(5) 1.1157(4) 0.0478(11) Uani 1 1 d . . . O2 O 0.4244(5) 0.4364(4) 0.6580(4) 0.0447(11) Uani 1 1 d . . . O3 O 0.7882(5) -0.0428(4) 0.7218(4) 0.0455(11) Uani 1 1 d . . . H100 H 0.328(9) 0.497(8) 0.919(7) 0.06(2) Uiso 1 1 d . . . H200 H 0.657(7) 0.157(7) 0.595(7) 0.042(16) Uiso 1 1 d . . . C5 C 0.0835(7) 0.7620(6) 0.1238(6) 0.0366(13) Uani 1 1 d . . . C6 C 0.0887(7) 0.7159(6) 0.3668(6) 0.0347(12) Uani 1 1 d . . . C7 C -0.1167(7) 0.9653(6) 0.3282(6) 0.0358(13) Uani 1 1 d . . . C8 C -0.0544(7) 0.9117(7) 0.1820(6) 0.0438(15) Uani 1 1 d . . . H8 H -0.1042 0.9755 0.1214 0.053 Uiso 1 1 calc R . . N3 N 0.1480(6) 0.6714(5) 0.2213(5) 0.0357(11) Uani 1 1 d . . . N4 N -0.0429(6) 0.8642(5) 0.4154(5) 0.0375(11) Uani 1 1 d . . . O5 O 0.1531(5) 0.7018(5) -0.0067(4) 0.0522(12) Uani 1 1 d . . . O6 O 0.1495(5) 0.6300(4) 0.4482(4) 0.0463(11) Uani 1 1 d . . . O7 O -0.2368(5) 1.1011(5) 0.3912(4) 0.0471(11) Uani 1 1 d . . . H300 H 0.241(7) 0.576(7) 0.178(6) 0.032(14) Uiso 1 1 d . . . H400 H -0.100(8) 0.907(8) 0.508(8) 0.055(19) Uiso 1 1 d . . . H500 H 0.476(8) 0.320(7) 0.268(7) 0.050(17) Uiso 1 1 d . . . H501 H 0.602(11) 0.225(10) 0.343(9) 0.10(3) Uiso 1 1 d . . . H502 H 0.428(8) 0.394(8) 0.420(7) 0.05(2) Uiso 1 1 d . . . H600 H 1.044(10) 0.192(9) 0.217(8) 0.08(2) Uiso 1 1 d . . . H601 H 0.904(10) 0.286(9) 0.162(9) 0.08(2) Uiso 1 1 d . . . H602 H 0.873(8) 0.310(8) 0.321(8) 0.05(2) Uiso 1 1 d . . . C9 C 0.3525(9) 0.2419(9) 0.4423(8) 0.0629(19) Uani 1 1 d . . . H9A H 0.3656 0.2101 0.5324 0.094 Uiso 1 1 calc R . . H9B H 0.3801 0.1519 0.3811 0.094 Uiso 1 1 calc R . . H9C H 0.2371 0.3193 0.4627 0.094 Uiso 1 1 calc R . . N5 N 0.4651(7) 0.3087(6) 0.3680(6) 0.0404(12) Uani 1 1 d . . . C10 C 1.0092(10) 0.4071(9) 0.1997(9) 0.067(2) Uani 1 1 d . . . H10A H 0.9160 0.5071 0.2037 0.100 Uiso 1 1 calc R . . H10B H 1.0961 0.3770 0.1030 0.100 Uiso 1 1 calc R . . H10C H 1.0548 0.4150 0.2688 0.100 Uiso 1 1 calc R . . N6 N 0.9500(7) 0.2893(6) 0.2351(6) 0.0405(12) 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 0.039(3) 0.037(3) 0.024(3) 0.005(2) -0.016(2) -0.011(2) C2 0.035(3) 0.030(3) 0.030(3) 0.002(2) -0.017(2) -0.006(2) C3 0.031(3) 0.032(3) 0.033(3) 0.003(2) -0.015(2) -0.006(2) C4 0.037(3) 0.032(3) 0.030(3) 0.001(2) -0.017(2) -0.002(2) N1 0.037(3) 0.032(2) 0.027(2) 0.0012(19) -0.015(2) 0.000(2) N2 0.034(2) 0.037(3) 0.028(2) -0.002(2) -0.015(2) -0.001(2) O1 0.048(2) 0.047(2) 0.024(2) -0.0038(17) -0.0169(18) 0.0010(19) O2 0.048(2) 0.039(2) 0.033(2) 0.0025(17) -0.0240(18) -0.0012(18) O3 0.048(2) 0.032(2) 0.036(2) -0.0015(17) -0.0188(18) 0.0003(18) C5 0.039(3) 0.034(3) 0.030(3) -0.003(2) -0.019(2) -0.006(2) C6 0.036(3) 0.032(3) 0.029(3) 0.003(2) -0.014(2) -0.009(2) C7 0.031(3) 0.033(3) 0.030(3) -0.003(2) -0.010(2) -0.004(2) C8 0.036(3) 0.046(3) 0.037(3) 0.004(3) -0.024(3) -0.001(3) N3 0.036(3) 0.033(2) 0.027(2) 0.0019(19) -0.017(2) -0.004(2) N4 0.037(3) 0.033(2) 0.029(2) 0.000(2) -0.014(2) -0.004(2) O5 0.055(3) 0.045(2) 0.033(2) -0.0087(18) -0.0242(19) 0.0040(19) O6 0.050(2) 0.037(2) 0.032(2) 0.0028(17) -0.0198(19) -0.0004(18) O7 0.042(2) 0.039(2) 0.032(2) -0.0007(17) -0.0156(18) 0.0064(18) C9 0.071(5) 0.061(4) 0.065(5) 0.014(4) -0.033(4) -0.033(4) N5 0.043(3) 0.036(3) 0.034(3) 0.000(2) -0.021(2) -0.006(2) C10 0.070(5) 0.075(5) 0.076(5) 0.025(4) -0.036(4) -0.046(4) N6 0.037(3) 0.039(3) 0.036(3) 0.004(2) -0.018(2) -0.008(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.256(6) . ? C1 C4 1.382(7) . ? C1 N1 1.391(6) . ? C2 O2 1.227(6) . ? C2 N2 1.349(6) . ? C2 N1 1.366(6) . ? C3 O3 1.262(6) . ? C3 C4 1.388(7) . ? C3 N2 1.393(7) . ? C4 H4 0.9300 . ? N1 H100 0.94(7) . ? N2 H200 0.94(6) . ? C5 O5 1.248(6) . ? C5 N3 1.386(6) . ? C5 C8 1.400(7) . ? C6 O6 1.224(6) . ? C6 N3 1.356(7) . ? C6 N4 1.363(7) . ? C7 O7 1.273(6) . ? C7 C8 1.377(7) . ? C7 N4 1.384(7) . ? C8 H8 0.9300 . ? N3 H300 0.92(6) . ? N4 H400 0.89(7) . ? C9 N5 1.446(9) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? N5 H500 0.97(7) . ? N5 H501 1.12(9) . ? N5 H502 0.85(7) . ? C10 N6 1.449(8) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? N6 H600 0.92(8) . ? N6 H601 0.99(8) . ? N6 H602 0.86(7) . ? 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 O1 C1 C4 127.5(5) . . ? O1 C1 N1 115.4(5) . . ? C4 C1 N1 117.1(5) . . ? O2 C2 N2 122.7(5) . . ? O2 C2 N1 122.0(5) . . ? N2 C2 N1 115.3(5) . . ? O3 C3 C4 126.3(5) . . ? O3 C3 N2 116.6(5) . . ? C4 C3 N2 117.1(5) . . ? C1 C4 C3 120.9(5) . . ? C1 C4 H4 119.5 . . ? C3 C4 H4 119.5 . . ? C2 N1 C1 124.6(4) . . ? C2 N1 H100 114(4) . . ? C1 N1 H100 121(4) . . ? C2 N2 C3 124.8(5) . . ? C2 N2 H200 121(4) . . ? C3 N2 H200 114(4) . . ? O5 C5 N3 117.0(5) . . ? O5 C5 C8 126.4(5) . . ? N3 C5 C8 116.6(5) . . ? O6 C6 N3 122.7(5) . . ? O6 C6 N4 122.5(5) . . ? N3 C6 N4 114.8(5) . . ? O7 C7 C8 125.8(5) . . ? O7 C7 N4 116.5(5) . . ? C8 C7 N4 117.8(5) . . ? C7 C8 C5 120.5(5) . . ? C7 C8 H8 119.7 . . ? C5 C8 H8 119.7 . . ? C6 N3 C5 125.5(5) . . ? C6 N3 H300 121(3) . . ? C5 N3 H300 114(3) . . ? C6 N4 C7 124.7(5) . . ? C6 N4 H400 125(4) . . ? C7 N4 H400 110(4) . . ? N5 C9 H9A 109.5 . . ? N5 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N5 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C9 N5 H500 112(4) . . ? C9 N5 H501 113(4) . . ? H500 N5 H501 97(5) . . ? C9 N5 H502 106(4) . . ? H500 N5 H502 114(6) . . ? H501 N5 H502 114(6) . . ? N6 C10 H10A 109.5 . . ? N6 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? N6 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C10 N6 H600 108(5) . . ? C10 N6 H601 107(4) . . ? H600 N6 H601 105(6) . . ? C10 N6 H602 113(4) . . ? H600 N6 H602 114(6) . . ? H601 N6 H602 109(6) . . ? _diffrn_measured_fraction_theta_max 0.909 _diffrn_reflns_theta_full 28.55 _diffrn_measured_fraction_theta_full 0.909 _refine_diff_density_max 0.454 _refine_diff_density_min -0.360 _refine_diff_density_rms 0.111 # Attachment '1c.CIF' data_fab_1c _database_code_depnum_ccdc_archive 'CCDC 294127' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H11 N3 O3' _chemical_formula_weight 173.18 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 Pnma loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z+1/2' '-x, y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z-1/2' 'x, -y-1/2, z' _cell_length_a 14.023(9) _cell_length_b 12.02(2) _cell_length_c 9.949(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1677(3) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 8.00 _cell_measurement_theta_max 15.00 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.372 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736 _exptl_absorpt_coefficient_mu 0.111 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.88 _exptl_absorpt_correction_T_max 1.00 _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 ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2929 _diffrn_reflns_av_R_equivalents 0.1444 _diffrn_reflns_av_sigmaI/netI 0.1114 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.36 _diffrn_reflns_theta_max 25.07 _reflns_number_total 1551 _reflns_number_gt 933 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0851P)^2^+0.0024P] 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 SHELXL _refine_ls_extinction_coef 0.023(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1551 _refine_ls_number_parameters 131 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1003 _refine_ls_R_factor_gt 0.0617 _refine_ls_wR_factor_ref 0.1661 _refine_ls_wR_factor_gt 0.1416 _refine_ls_goodness_of_fit_ref 0.996 _refine_ls_restrained_S_all 0.996 _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 C1 C 1.0643(3) 0.7500 0.2296(3) 0.0438(9) Uani 1 2 d S . . C2 C 0.9295(2) 0.85070(16) 0.1343(2) 0.0426(6) Uani 1 1 d . . . C3 C 0.8855(3) 0.7500 0.1040(3) 0.0465(9) Uani 1 2 d S . . H3 H 0.8257 0.7500 0.0636 0.072(13) Uiso 1 2 d SR . . N1 N 1.01739(16) 0.84600(15) 0.19608(18) 0.0465(6) Uani 1 1 d . . . H1 H 1.0447 0.9080 0.2153 0.053(8) Uiso 1 1 d R . . O1 O 1.1428(2) 0.7500 0.2853(3) 0.0579(8) Uani 1 2 d S . . O2 O 0.89655(14) 0.94781(13) 0.11067(17) 0.0529(6) Uani 1 1 d . . . C4 C 1.0582(3) 0.7500 -0.1547(3) 0.0456(9) Uani 1 2 d S . . C5 C 0.9226(2) 0.85064(16) -0.2463(2) 0.0457(7) Uani 1 1 d . . . C6 C 0.8787(3) 0.7500 -0.2768(3) 0.0483(10) Uani 1 2 d S . . H6 H 0.8192 0.7500 -0.3181 0.060(12) Uiso 1 2 d SR . . N2 N 1.01067(16) 0.84602(14) -0.18492(18) 0.0456(6) Uani 1 1 d . . . H2 H 1.0374 0.9080 -0.1638 0.051(7) Uiso 1 1 d R . . O3 O 1.1383(2) 0.7500 -0.1061(3) 0.0647(8) Uani 1 2 d S . . O4 O 0.88910(14) 0.94732(13) -0.27062(18) 0.0599(6) Uani 1 1 d . . . N3 N 0.71938(18) 1.00058(15) 0.00591(19) 0.0492(6) Uani 1 1 d . . . H3B H 0.7780 0.9765 0.0286 0.063(8) Uiso 1 1 d R . . H3C H 0.6894 1.0217 0.0817 0.063(9) Uiso 1 1 d R . . C7 C 0.7282(3) 1.0974(2) -0.0846(3) 0.0644(9) Uani 1 1 d . . . H7A H 0.7636 1.1552 -0.0404 0.124(14) Uiso 1 1 d R . . H7B H 0.6658 1.1245 -0.1073 0.087(12) Uiso 1 1 d R . . H7C H 0.7610 1.0754 -0.1650 0.085(11) Uiso 1 1 d R . . C8 C 0.6662(3) 0.9093(2) -0.0564(3) 0.0717(10) Uani 1 1 d . . . H8A H 0.6613 0.8486 0.0059 0.151(18) Uiso 1 1 d R . . H8B H 0.6991 0.8849 -0.1358 0.090(11) Uiso 1 1 d R . . H8C H 0.6035 0.9345 -0.0802 0.084(12) Uiso 1 1 d 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 0.070(3) 0.0078(15) 0.054(2) 0.000 -0.0013(18) 0.000 C2 0.0699(16) 0.0054(11) 0.0526(14) 0.0009(8) -0.0014(12) 0.0029(11) C3 0.071(3) 0.0062(17) 0.062(2) 0.000 -0.0071(17) 0.000 N1 0.0727(15) 0.0031(10) 0.0639(12) -0.0005(7) -0.0060(11) -0.0021(9) O1 0.080(2) 0.0141(13) 0.0792(18) 0.000 -0.0160(15) 0.000 O2 0.0794(13) 0.0037(9) 0.0756(12) 0.0012(7) -0.0095(9) 0.0044(8) C4 0.070(3) 0.0099(15) 0.057(2) 0.000 -0.0020(19) 0.000 C5 0.0797(18) 0.0065(11) 0.0509(13) 0.0018(9) -0.0074(13) 0.0042(11) C6 0.075(3) 0.0064(16) 0.063(2) 0.000 -0.0136(19) 0.000 N2 0.0747(15) 0.0027(10) 0.0593(12) 0.0014(7) -0.0058(11) -0.0043(9) O3 0.079(2) 0.0198(15) 0.096(2) 0.000 -0.0180(16) 0.000 O4 0.0995(15) 0.0022(8) 0.0780(12) 0.0022(7) -0.0231(10) 0.0048(8) N3 0.0793(16) 0.0171(10) 0.0513(11) -0.0014(8) -0.0009(11) 0.0066(10) C7 0.109(3) 0.0183(14) 0.0662(17) 0.0047(11) -0.0047(17) -0.0113(16) C8 0.112(3) 0.0192(14) 0.084(2) -0.0009(13) -0.005(2) -0.0134(17) _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 O1 1.232(5) . ? C1 N1 1.369(3) 8_575 ? C1 N1 1.369(3) . ? C2 O2 1.277(3) . ? C2 N1 1.379(3) . ? C2 C3 1.391(3) . ? C3 C2 1.391(3) 8_575 ? C3 H3 0.9299 . ? N1 H1 0.8599 . ? C4 O3 1.224(5) . ? C4 N2 1.366(3) 8_575 ? C4 N2 1.366(3) . ? C5 O4 1.277(3) . ? C5 N2 1.379(4) . ? C5 C6 1.391(3) . ? C6 C5 1.391(3) 8_575 ? C6 H6 0.9301 . ? N2 H2 0.8604 . ? N3 C8 1.464(4) . ? N3 C7 1.477(3) . ? N3 H3B 0.9007 . ? N3 H3C 0.8996 . ? C7 H7A 0.9604 . ? C7 H7B 0.9599 . ? C7 H7C 0.9599 . ? C8 H8A 0.9599 . ? C8 H8B 0.9603 . ? C8 H8C 0.9603 . ? 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 O1 C1 N1 122.59(18) . 8_575 ? O1 C1 N1 122.59(18) . . ? N1 C1 N1 114.8(4) 8_575 . ? O2 C2 N1 116.3(2) . . ? O2 C2 C3 126.5(3) . . ? N1 C2 C3 117.2(2) . . ? C2 C3 C2 120.9(4) 8_575 . ? C2 C3 H3 119.5 8_575 . ? C2 C3 H3 119.5 . . ? C1 N1 C2 124.9(2) . . ? C1 N1 H1 117.5 . . ? C2 N1 H1 117.5 . . ? O3 C4 N2 122.33(17) . 8_575 ? O3 C4 N2 122.33(17) . . ? N2 C4 N2 115.3(3) 8_575 . ? O4 C5 N2 116.7(2) . . ? O4 C5 C6 126.0(3) . . ? N2 C5 C6 117.3(2) . . ? C5 C6 C5 120.8(4) . 8_575 ? C5 C6 H6 119.6 . . ? C5 C6 H6 119.6 8_575 . ? C4 N2 C5 124.6(2) . . ? C4 N2 H2 117.8 . . ? C5 N2 H2 117.6 . . ? C8 N3 C7 112.0(2) . . ? C8 N3 H3B 109.3 . . ? C7 N3 H3B 109.3 . . ? C8 N3 H3C 109.1 . . ? C7 N3 H3C 109.1 . . ? H3B N3 H3C 107.9 . . ? N3 C7 H7A 109.5 . . ? N3 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? N3 C7 H7C 109.3 . . ? H7A C7 H7C 109.4 . . ? H7B C7 H7C 109.5 . . ? N3 C8 H8A 109.4 . . ? N3 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N3 C8 H8C 109.5 . . ? H8A C8 H8C 109.4 . . ? H8B C8 H8C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.07 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.390 _refine_diff_density_min -0.301 _refine_diff_density_rms 0.071 # Attachment '1a.CIF' data_fab_1a _database_code_depnum_ccdc_archive 'CCDC 294128' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C4 H7 N3 O3' _chemical_formula_weight 145.13 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n 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 10.713(3) _cell_length_b 3.858(2) _cell_length_c 14.347(5) _cell_angle_alpha 90.00 _cell_angle_beta 96.15(3) _cell_angle_gamma 90.00 _cell_volume 589.6(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 8 _cell_measurement_theta_max 10 _exptl_crystal_description prism _exptl_crystal_colour 'light pink' _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.635 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 304 _exptl_absorpt_coefficient_mu 0.140 _exptl_absorpt_correction_type Psi-scan _exptl_absorpt_correction_T_min 0.81 _exptl_absorpt_correction_T_max 1.00 _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 scintillation _diffrn_measurement_method 'omega-two theta' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1202 _diffrn_reflns_av_R_equivalents 0.0268 _diffrn_reflns_av_sigmaI/netI 0.0388 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.83 _diffrn_reflns_theta_max 24.98 _reflns_number_total 1039 _reflns_number_gt 704 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Enraf Nonius software' _computing_cell_refinement 'Enraf Nonius software' _computing_data_reduction wingx _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics schakal _computing_publication_material wingX _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^)+(0.0729P)^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 SHELXL _refine_ls_extinction_coef 0.020(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1039 _refine_ls_number_parameters 120 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0751 _refine_ls_R_factor_gt 0.0389 _refine_ls_wR_factor_ref 0.1145 _refine_ls_wR_factor_gt 0.0974 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _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 C1 C 0.3149(2) 0.4978(6) 0.38776(17) 0.0210(5) Uani 1 1 d . . . O1 O 0.38459(15) 0.5850(5) 0.32584(12) 0.0295(5) Uani 1 1 d . . . N1 N 0.20785(18) 0.3054(5) 0.35743(14) 0.0221(5) Uani 1 1 d . . . H1 H 0.196(3) 0.243(8) 0.298(2) 0.037(8) Uiso 1 1 d . . . C2 C 0.1232(2) 0.1911(6) 0.41417(16) 0.0195(5) Uani 1 1 d . . . O2 O 0.03001(15) 0.0173(4) 0.38270(11) 0.0285(5) Uani 1 1 d . . . N2 N 0.14404(18) 0.2807(5) 0.50533(14) 0.0216(5) Uani 1 1 d . . . H2 H 0.091(2) 0.204(7) 0.5439(18) 0.020(6) Uiso 1 1 d . . . C3 C 0.2479(2) 0.4690(6) 0.54401(16) 0.0220(6) Uani 1 1 d . . . O3 O 0.25455(16) 0.5248(5) 0.63098(11) 0.0312(5) Uani 1 1 d . . . C4 C 0.3333(2) 0.5755(7) 0.48312(17) 0.0246(6) Uani 1 1 d . . . H4 H 0.409(3) 0.723(8) 0.5087(19) 0.043(8) Uiso 1 1 d . . . N3 N 0.4287(2) 0.9402(7) 0.73152(17) 0.0274(6) Uani 1 1 d . . . H5 H 0.386(3) 1.025(8) 0.777(2) 0.040(9) Uiso 1 1 d . . . H6 H 0.471(3) 1.097(10) 0.699(2) 0.048(9) Uiso 1 1 d . . . H7 H 0.485(4) 0.780(12) 0.756(3) 0.068(12) Uiso 1 1 d . . . H8 H 0.368(3) 0.823(9) 0.689(2) 0.054(10) 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 C1 0.0199(12) 0.0221(12) 0.0211(12) 0.0041(11) 0.0034(9) 0.0034(10) O1 0.0273(9) 0.0377(11) 0.0246(10) 0.0023(8) 0.0075(7) -0.0061(8) N1 0.0221(10) 0.0278(11) 0.0161(10) -0.0020(9) 0.0008(8) -0.0042(9) C2 0.0196(12) 0.0213(12) 0.0177(11) -0.0015(10) 0.0021(9) 0.0009(10) O2 0.0264(9) 0.0381(11) 0.0207(9) -0.0042(8) 0.0008(7) -0.0120(8) N2 0.0205(10) 0.0279(11) 0.0167(10) -0.0010(9) 0.0037(8) -0.0050(9) C3 0.0232(12) 0.0246(12) 0.0173(12) -0.0007(10) -0.0022(9) 0.0010(11) O3 0.0323(10) 0.0452(11) 0.0162(9) -0.0050(8) 0.0026(7) -0.0113(9) C4 0.0209(12) 0.0281(13) 0.0244(13) -0.0001(11) 0.0004(10) -0.0022(11) N3 0.0267(12) 0.0287(12) 0.0268(13) -0.0027(11) 0.0025(11) -0.0013(11) _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 O1 1.266(3) . ? C1 C4 1.394(3) . ? C1 N1 1.396(3) . ? N1 C2 1.356(3) . ? N1 H1 0.89(3) . ? C2 O2 1.246(3) . ? C2 N2 1.348(3) . ? N2 C3 1.393(3) . ? N2 H2 0.89(3) . ? C3 O3 1.261(3) . ? C3 C4 1.394(3) . ? C4 H4 1.03(3) . ? N3 H5 0.90(3) . ? N3 H6 0.91(4) . ? N3 H7 0.91(5) . ? N3 H8 0.96(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 O1 C1 C4 126.9(2) . . ? O1 C1 N1 116.7(2) . . ? C4 C1 N1 116.5(2) . . ? C2 N1 C1 124.5(2) . . ? C2 N1 H1 117.4(18) . . ? C1 N1 H1 118.1(18) . . ? O2 C2 N2 122.2(2) . . ? O2 C2 N1 121.3(2) . . ? N2 C2 N1 116.6(2) . . ? C2 N2 C3 124.2(2) . . ? C2 N2 H2 118.0(16) . . ? C3 N2 H2 117.7(16) . . ? O3 C3 C4 126.8(2) . . ? O3 C3 N2 116.2(2) . . ? C4 C3 N2 117.0(2) . . ? C3 C4 C1 121.2(2) . . ? C3 C4 H4 119.1(15) . . ? C1 C4 H4 119.6(15) . . ? H5 N3 H6 117(3) . . ? H5 N3 H7 109(3) . . ? H6 N3 H7 108(3) . . ? H5 N3 H8 106(3) . . ? H6 N3 H8 109(3) . . ? H7 N3 H8 108(3) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 24.98 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.267 _refine_diff_density_min -0.248 _refine_diff_density_rms 0.056