# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Ashwini Nangia' _publ_contact_author_email ashwini.nangia@gmail.com loop_ _publ_author_name A.Nangia S.Cherukuvada data_2INH-1FA-100K _database_code_depnum_ccdc_archive 'CCDC 849827' #TrackingRef '- INH-FA-100 K.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H18 N6 O6' _chemical_formula_weight 390.36 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 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 7.883(2) _cell_length_b 8.697(3) _cell_length_c 12.506(4) _cell_angle_alpha 90.00 _cell_angle_beta 97.74(3) _cell_angle_gamma 90.00 _cell_volume 849.5(4) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5352 _cell_measurement_theta_min 2.86 _cell_measurement_theta_max 26.04 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.526 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 408 _exptl_absorpt_coefficient_mu 0.120 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9581 _exptl_absorpt_correction_T_max 0.9764 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 8546 _diffrn_reflns_av_R_equivalents 0.0327 _diffrn_reflns_av_sigmaI/netI 0.0237 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.86 _diffrn_reflns_theta_max 26.01 _reflns_number_total 1677 _reflns_number_gt 1557 _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 ; 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^)+(0.0440P)^2^+0.3836P] 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 1677 _refine_ls_number_parameters 143 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0435 _refine_ls_R_factor_gt 0.0397 _refine_ls_wR_factor_ref 0.0968 _refine_ls_wR_factor_gt 0.0942 _refine_ls_goodness_of_fit_ref 1.114 _refine_ls_restrained_S_all 1.114 _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 0.54351(18) 0.87749(17) 0.78543(12) 0.0172(3) Uani 1 1 d . . . C2 C 0.46266(18) 0.75170(16) 0.84475(11) 0.0164(3) Uani 1 1 d . . . C3 C 0.47011(19) 0.60208(17) 0.80646(12) 0.0190(3) Uani 1 1 d . . . H3 H 0.5317 0.5800 0.7480 0.023 Uiso 1 1 calc R . . C4 C 0.38745(18) 0.48591(17) 0.85389(12) 0.0183(3) Uani 1 1 d . . . H4 H 0.3912 0.3840 0.8269 0.022 Uiso 1 1 calc R . . C5 C 0.29900(18) 0.65667(17) 0.97792(12) 0.0183(3) Uani 1 1 d . . . H5 H 0.2410 0.6744 1.0386 0.022 Uiso 1 1 calc R . . C6 C 0.37781(18) 0.77790(17) 0.93387(12) 0.0177(3) Uani 1 1 d . . . H6 H 0.3744 0.8781 0.9638 0.021 Uiso 1 1 calc R . . C7 C 0.14024(18) 0.17930(16) 0.98506(12) 0.0167(3) Uani 1 1 d . . . C8 C 0.01973(18) 0.06652(17) 1.02460(11) 0.0177(3) Uani 1 1 d . . . H8 H -0.0306 0.0910 1.0874 0.021 Uiso 1 1 calc R . . H2 H 0.412(2) 1.038(2) 0.8427(15) 0.029(5) Uiso 1 1 d . . . H1A H 0.650(3) 1.178(2) 0.7736(15) 0.029(5) Uiso 1 1 d . . . H3A H 0.227(3) 0.411(3) 0.9785(18) 0.063(7) Uiso 1 1 d . . . H1B H 0.550(2) 1.119(2) 0.6787(16) 0.027(5) Uiso 1 1 d . . . N1 N 0.53947(18) 1.14936(15) 0.74576(12) 0.0214(3) Uani 1 1 d . . . N2 N 0.49334(16) 1.02057(14) 0.80524(10) 0.0185(3) Uani 1 1 d . . . N3 N 0.30206(15) 0.51425(14) 0.93730(10) 0.0179(3) Uani 1 1 d . . . O1 O 0.64412(14) 0.84779(12) 0.72158(9) 0.0253(3) Uani 1 1 d . . . O2 O 0.23952(14) 0.14144(12) 0.92180(9) 0.0225(3) Uani 1 1 d . . . O3 O 0.12763(13) 0.31651(12) 1.02202(9) 0.0210(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 0.0160(7) 0.0169(7) 0.0187(7) 0.0010(6) 0.0031(6) -0.0001(5) C2 0.0143(7) 0.0160(7) 0.0184(7) 0.0011(6) 0.0009(6) 0.0002(5) C3 0.0203(7) 0.0180(8) 0.0188(7) -0.0009(6) 0.0034(6) 0.0016(6) C4 0.0200(7) 0.0135(7) 0.0209(8) -0.0013(6) 0.0009(6) 0.0003(6) C5 0.0181(7) 0.0167(7) 0.0207(8) 0.0003(6) 0.0045(6) 0.0007(5) C6 0.0187(7) 0.0132(7) 0.0216(8) -0.0009(6) 0.0035(6) -0.0001(5) C7 0.0172(7) 0.0149(7) 0.0181(7) 0.0007(5) 0.0026(5) -0.0006(5) C8 0.0193(7) 0.0160(7) 0.0189(7) 0.0016(6) 0.0062(6) 0.0013(6) N1 0.0263(7) 0.0150(7) 0.0252(7) 0.0038(5) 0.0119(6) -0.0011(5) N2 0.0210(7) 0.0140(6) 0.0227(7) 0.0017(5) 0.0103(5) -0.0007(5) N3 0.0166(6) 0.0151(6) 0.0218(7) 0.0019(5) 0.0023(5) -0.0008(5) O1 0.0297(6) 0.0187(6) 0.0312(6) 0.0037(5) 0.0176(5) 0.0042(4) O2 0.0227(6) 0.0173(6) 0.0302(6) -0.0030(4) 0.0131(5) -0.0024(4) O3 0.0265(6) 0.0130(5) 0.0257(6) -0.0029(4) 0.0111(5) -0.0037(4) _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 1.2264(18) . ? C1 N2 1.3389(19) . ? C1 C2 1.510(2) . ? C2 C3 1.391(2) . ? C2 C6 1.394(2) . ? C3 C4 1.379(2) . ? C4 N3 1.3384(19) . ? C5 N3 1.3402(19) . ? C5 C6 1.376(2) . ? C7 O2 1.2304(18) . ? C7 O3 1.2883(18) . ? C7 C8 1.495(2) . ? C8 C8 1.328(3) 3_557 ? N1 N2 1.4188(17) . ? 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 N2 123.32(13) . . ? O1 C1 C2 121.33(13) . . ? N2 C1 C2 115.31(12) . . ? C3 C2 C6 118.39(13) . . ? C3 C2 C1 117.94(13) . . ? C6 C2 C1 123.66(13) . . ? C4 C3 C2 119.55(14) . . ? N3 C4 C3 121.12(14) . . ? N3 C5 C6 121.61(14) . . ? C5 C6 C2 119.09(14) . . ? O2 C7 O3 124.41(13) . . ? O2 C7 C8 121.64(13) . . ? O3 C7 C8 113.95(13) . . ? C8 C8 C7 122.55(17) 3_557 . ? C1 N2 N1 122.26(12) . . ? C4 N3 C5 120.15(13) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.01 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.220 _refine_diff_density_min -0.228 _refine_diff_density_rms 0.055 # Attachment '- INH-FA-298 K.cif' data_2INH-1FA-298K _database_code_depnum_ccdc_archive 'CCDC 849828' #TrackingRef '- INH-FA-298 K.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H18 N6 O6' _chemical_formula_weight 390.36 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 Monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' 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 8.1339(3) _cell_length_b 8.7424(4) _cell_length_c 12.4779(5) _cell_angle_alpha 90.00 _cell_angle_beta 96.933(4) _cell_angle_gamma 90.00 _cell_volume 880.81(6) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2372 _cell_measurement_theta_min 2.8345 _cell_measurement_theta_max 28.7929 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.472 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 408 _exptl_absorpt_coefficient_mu 0.115 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.99050 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 'Xcalibur, Eos, Gemini' _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 3941 _diffrn_reflns_av_R_equivalents 0.0154 _diffrn_reflns_av_sigmaI/netI 0.0227 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.84 _diffrn_reflns_theta_max 26.36 _reflns_number_total 1794 _reflns_number_gt 1512 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0426P)^2^+0.1654P] 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 0.012(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1794 _refine_ls_number_parameters 144 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0447 _refine_ls_R_factor_gt 0.0366 _refine_ls_wR_factor_ref 0.0956 _refine_ls_wR_factor_gt 0.0897 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _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 0.54486(17) 0.87454(16) 0.78858(11) 0.0361(3) Uani 1 1 d . . . C2 C 0.46351(16) 0.74884(15) 0.84610(11) 0.0325(3) Uani 1 1 d . . . C3 C 0.47321(18) 0.60061(17) 0.80803(11) 0.0400(4) Uani 1 1 d . . . H3 H 0.5349 0.5793 0.7518 0.048 Uiso 1 1 calc R . . C4 C 0.39043(19) 0.48476(17) 0.85437(12) 0.0417(4) Uani 1 1 d . . . H4 H 0.3957 0.3858 0.8276 0.050 Uiso 1 1 calc R . . C5 C 0.29797(18) 0.65266(17) 0.97664(12) 0.0402(4) Uani 1 1 d . . . H5 H 0.2399 0.6697 1.0353 0.048 Uiso 1 1 calc R . . C6 C 0.37600(17) 0.77379(17) 0.93372(11) 0.0373(3) Uani 1 1 d . . . H6 H 0.3703 0.8712 0.9629 0.045 Uiso 1 1 calc R . . C7 C 0.13938(17) 0.17567(15) 0.98400(11) 0.0339(3) Uani 1 1 d . . . C8 C 0.01869(17) 0.06632(16) 1.02327(11) 0.0356(3) Uani 1 1 d . . . H8 H -0.0323 0.0932 1.0834 0.043 Uiso 1 1 calc R . . H2 H 0.406(2) 1.034(2) 0.8411(14) 0.058(5) Uiso 1 1 d . . . H1A H 0.643(3) 1.168(2) 0.7779(16) 0.072(7) Uiso 1 1 d . . . H3A H 0.215(3) 0.400(3) 0.9754(16) 0.090(7) Uiso 1 1 d . . . H1B H 0.544(2) 1.115(2) 0.6795(16) 0.066(6) Uiso 1 1 d . . . N1 N 0.5419(2) 1.14518(16) 0.74802(14) 0.0504(4) Uani 1 1 d . . . N2 N 0.49186(16) 1.01640(14) 0.80490(10) 0.0397(3) Uani 1 1 d . . . N3 N 0.30319(14) 0.51090(13) 0.93643(10) 0.0385(3) Uani 1 1 d . . . O1 O 0.64976(16) 0.84637(13) 0.72853(10) 0.0625(4) Uani 1 1 d . . . O2 O 0.23929(14) 0.13592(12) 0.92396(10) 0.0531(3) Uani 1 1 d . . . O3 O 0.12529(14) 0.31364(11) 1.01814(9) 0.0476(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 0.0368(7) 0.0326(8) 0.0411(7) 0.0032(6) 0.0140(6) 0.0014(6) C2 0.0323(7) 0.0278(7) 0.0381(7) 0.0030(6) 0.0068(5) 0.0000(5) C3 0.0476(8) 0.0333(8) 0.0412(7) -0.0027(6) 0.0134(6) 0.0019(6) C4 0.0495(9) 0.0260(8) 0.0496(8) -0.0034(6) 0.0063(7) -0.0018(6) C5 0.0430(8) 0.0319(8) 0.0487(8) 0.0025(6) 0.0174(6) -0.0016(6) C6 0.0423(8) 0.0261(7) 0.0459(8) -0.0008(6) 0.0155(6) -0.0015(6) C7 0.0362(7) 0.0269(7) 0.0404(7) -0.0009(6) 0.0118(6) -0.0045(6) C8 0.0387(7) 0.0278(7) 0.0434(8) -0.0005(6) 0.0173(6) -0.0036(6) N1 0.0590(10) 0.0321(7) 0.0660(10) 0.0104(7) 0.0313(8) -0.0010(6) N2 0.0444(7) 0.0272(7) 0.0523(7) 0.0046(5) 0.0250(6) -0.0009(5) N3 0.0376(7) 0.0282(7) 0.0503(7) 0.0042(5) 0.0074(5) -0.0045(5) O1 0.0717(8) 0.0425(7) 0.0841(9) 0.0125(6) 0.0531(7) 0.0130(6) O2 0.0537(7) 0.0363(6) 0.0768(8) -0.0095(6) 0.0392(6) -0.0083(5) O3 0.0600(7) 0.0259(6) 0.0627(7) -0.0077(5) 0.0306(5) -0.0115(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.2266(17) . ? C1 N2 1.3367(18) . ? C1 C2 1.5083(19) . ? C2 C3 1.386(2) . ? C2 C6 1.3920(19) . ? C3 C4 1.381(2) . ? C4 N3 1.3340(18) . ? C5 N3 1.3396(18) . ? C5 C6 1.376(2) . ? C7 O2 1.2205(17) . ? C7 O3 1.2889(16) . ? C7 C8 1.4946(19) . ? C8 C8 1.316(3) 3_557 ? N1 N2 1.4165(17) . ? 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 N2 122.70(13) . . ? O1 C1 C2 121.46(13) . . ? N2 C1 C2 115.81(12) . . ? C3 C2 C6 118.13(12) . . ? C3 C2 C1 118.15(12) . . ? C6 C2 C1 123.70(12) . . ? C4 C3 C2 119.43(13) . . ? N3 C4 C3 121.81(13) . . ? N3 C5 C6 121.96(13) . . ? C5 C6 C2 119.26(13) . . ? O2 C7 O3 124.17(13) . . ? O2 C7 C8 122.11(13) . . ? O3 C7 C8 113.71(12) . . ? C8 C8 C7 123.02(16) 3_557 . ? C1 N2 N1 122.93(12) . . ? C4 N3 C5 119.33(12) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.36 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.190 _refine_diff_density_min -0.162 _refine_diff_density_rms 0.034 # Attachment '- INH-SA.cif' data_2INH-1SA _database_code_depnum_ccdc_archive 'CCDC 849829' #TrackingRef '- INH-SA.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H10 N3 O3' _chemical_formula_weight 196.19 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 6.971(6) _cell_length_b 19.508(17) _cell_length_c 7.260(6) _cell_angle_alpha 90.00 _cell_angle_beta 114.603(13) _cell_angle_gamma 90.00 _cell_volume 897.7(13) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2926 _cell_measurement_theta_min 3.09 _cell_measurement_theta_max 25.84 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.452 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 412 _exptl_absorpt_coefficient_mu 0.113 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.9614 _exptl_absorpt_correction_T_max 0.9832 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 9228 _diffrn_reflns_av_R_equivalents 0.0382 _diffrn_reflns_av_sigmaI/netI 0.0245 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 26.15 _reflns_number_total 1784 _reflns_number_gt 1563 _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 ; 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^)+(0.0763P)^2^+0.1817P] 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 1784 _refine_ls_number_parameters 143 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0551 _refine_ls_R_factor_gt 0.0486 _refine_ls_wR_factor_ref 0.1356 _refine_ls_wR_factor_gt 0.1301 _refine_ls_goodness_of_fit_ref 1.085 _refine_ls_restrained_S_all 1.085 _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 0.1932(3) 0.10705(8) 0.4426(3) 0.0364(4) Uani 1 1 d . . . C2 C 0.2970(2) 0.17557(8) 0.4585(2) 0.0350(4) Uani 1 1 d . . . C3 C 0.1959(3) 0.23297(9) 0.4845(3) 0.0422(4) Uani 1 1 d . . . H3 H 0.0707 0.2287 0.5003 0.051 Uiso 1 1 calc R . . C4 C 0.2815(3) 0.29660(9) 0.4869(3) 0.0463(5) Uani 1 1 d . . . H4 H 0.2121 0.3349 0.5053 0.056 Uiso 1 1 calc R . . C5 C 0.5572(3) 0.25049(9) 0.4402(3) 0.0426(4) Uani 1 1 d . . . H5 H 0.6823 0.2564 0.4251 0.051 Uiso 1 1 calc R . . C6 C 0.4830(3) 0.18492(9) 0.4367(3) 0.0413(4) Uani 1 1 d . . . H6 H 0.5569 0.1475 0.4199 0.050 Uiso 1 1 calc R . . C7 C 0.7977(2) 0.42932(8) 0.4752(3) 0.0363(4) Uani 1 1 d . . . C8 C 0.8904(3) 0.49970(9) 0.4963(3) 0.0400(4) Uani 1 1 d . . . H8A H 0.8944 0.5205 0.6192 0.048 Uiso 1 1 calc R . . H8B H 0.7992 0.5275 0.3829 0.048 Uiso 1 1 calc R . . H2 H 0.448(3) 0.0572(9) 0.496(3) 0.037(5) Uiso 1 1 d . . . H1A H 0.180(4) -0.0247(12) 0.510(3) 0.065(7) Uiso 1 1 d . . . H3A H 0.563(4) 0.3819(16) 0.463(4) 0.088(8) Uiso 1 1 d . . . H1B H 0.146(4) -0.0159(11) 0.300(3) 0.058(6) Uiso 1 1 d . . . N1 N 0.2421(2) -0.01465(7) 0.4302(3) 0.0437(4) Uani 1 1 d . . . N2 N 0.3173(2) 0.05322(7) 0.4663(2) 0.0418(4) Uani 1 1 d . . . N3 N 0.4587(2) 0.30558(7) 0.4641(2) 0.0423(4) Uani 1 1 d . . . O1 O 0.00688(19) 0.10217(6) 0.4064(2) 0.0514(4) Uani 1 1 d . . . O2 O 0.8858(2) 0.37817(7) 0.4640(3) 0.0694(5) Uani 1 1 d . . . O3 O 0.60855(19) 0.42927(7) 0.4712(2) 0.0492(4) 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 0.0322(8) 0.0368(9) 0.0419(9) 0.0003(7) 0.0172(7) -0.0032(6) C2 0.0299(8) 0.0354(9) 0.0389(8) 0.0008(6) 0.0134(7) -0.0011(6) C3 0.0316(8) 0.0405(9) 0.0588(11) -0.0026(8) 0.0231(8) -0.0006(7) C4 0.0370(9) 0.0354(9) 0.0691(12) -0.0050(8) 0.0245(9) 0.0023(7) C5 0.0330(9) 0.0409(9) 0.0597(11) 0.0008(8) 0.0248(8) -0.0026(7) C6 0.0358(9) 0.0352(9) 0.0581(10) -0.0015(7) 0.0247(8) 0.0000(7) C7 0.0315(8) 0.0345(9) 0.0444(9) 0.0039(7) 0.0174(7) 0.0019(6) C8 0.0367(9) 0.0338(9) 0.0520(10) -0.0010(7) 0.0211(8) -0.0030(7) N1 0.0354(8) 0.0316(8) 0.0667(11) -0.0005(7) 0.0238(8) -0.0059(6) N2 0.0280(8) 0.0325(7) 0.0622(10) -0.0010(6) 0.0161(7) -0.0041(6) N3 0.0351(8) 0.0340(7) 0.0576(9) 0.0001(6) 0.0190(7) -0.0027(6) O1 0.0344(7) 0.0417(7) 0.0836(10) 0.0028(6) 0.0301(7) -0.0044(5) O2 0.0508(8) 0.0354(7) 0.1382(15) -0.0018(8) 0.0554(9) 0.0015(6) O3 0.0361(7) 0.0327(7) 0.0842(10) 0.0013(6) 0.0303(7) -0.0013(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.217(2) . ? C1 N2 1.326(2) . ? C1 C2 1.501(2) . ? C2 C3 1.378(2) . ? C2 C6 1.382(3) . ? C3 C4 1.374(3) . ? C4 N3 1.324(2) . ? C5 N3 1.325(2) . ? C5 C6 1.376(3) . ? C7 O2 1.192(2) . ? C7 O3 1.307(2) . ? C7 C8 1.498(3) . ? C8 C8 1.506(4) 3_766 ? N1 N2 1.408(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 O1 C1 N2 123.12(15) . . ? O1 C1 C2 121.56(15) . . ? N2 C1 C2 115.30(16) . . ? C3 C2 C6 117.81(15) . . ? C3 C2 C1 118.44(16) . . ? C6 C2 C1 123.63(15) . . ? C4 C3 C2 119.45(17) . . ? N3 C4 C3 122.72(16) . . ? N3 C5 C6 123.01(16) . . ? C5 C6 C2 118.93(16) . . ? O2 C7 O3 122.82(16) . . ? O2 C7 C8 124.14(16) . . ? O3 C7 C8 113.04(14) . . ? C7 C8 C8 113.51(18) . 3_766 ? C1 N2 N1 123.25(15) . . ? C4 N3 C5 118.07(15) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 26.15 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.226 _refine_diff_density_min -0.229 _refine_diff_density_rms 0.063 # Attachment '- PZA-FA.cif' data_2PZA-1FA _database_code_depnum_ccdc_archive 'CCDC 849830' #TrackingRef '- PZA-FA.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C7 H7 N3 O3' _chemical_formula_weight 181.16 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 1 21/n 1' 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 3.7408(7) _cell_length_b 17.352(2) _cell_length_c 12.558(2) _cell_angle_alpha 90.00 _cell_angle_beta 95.760(16) _cell_angle_gamma 90.00 _cell_volume 811.0(2) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1056 _cell_measurement_theta_min 2.8525 _cell_measurement_theta_max 29.0501 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.484 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 376 _exptl_absorpt_coefficient_mu 0.119 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9652 _exptl_absorpt_correction_T_max 0.9882 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 'Xcalibur, Eos, Gemini' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.3291 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3083 _diffrn_reflns_av_R_equivalents 0.0311 _diffrn_reflns_av_sigmaI/netI 0.0516 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.86 _diffrn_reflns_theta_max 26.36 _reflns_number_total 1656 _reflns_number_gt 1194 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0599P)^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 0.015(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1656 _refine_ls_number_parameters 131 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0739 _refine_ls_R_factor_gt 0.0520 _refine_ls_wR_factor_ref 0.1351 _refine_ls_wR_factor_gt 0.1146 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.040 _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 0.6576(6) 0.91052(12) 0.60075(17) 0.0393(5) Uani 1 1 d . . . C2 C 0.7531(5) 0.84806(11) 0.68023(16) 0.0323(5) Uani 1 1 d . . . C3 C 1.0187(5) 0.80892(12) 0.84170(16) 0.0377(5) Uani 1 1 d . . . H3 H 1.1560 0.8192 0.9060 0.045 Uiso 1 1 calc R . . C4 C 0.8909(5) 0.73475(12) 0.82155(17) 0.0389(5) Uani 1 1 d . . . H4 H 0.9418 0.6966 0.8728 0.047 Uiso 1 1 calc R . . C5 C 0.6318(5) 0.77366(11) 0.65921(16) 0.0351(5) Uani 1 1 d . . . H5 H 0.5016 0.7629 0.5939 0.042 Uiso 1 1 calc R . . C6 C 0.2112(5) 0.58154(11) 0.58700(16) 0.0320(5) Uani 1 1 d . . . C7 C 0.0820(4) 0.50524(11) 0.54806(15) 0.0341(5) Uani 1 1 d . . . H7 H 0.1182 0.4630 0.5934 0.041 Uiso 1 1 calc R . . H2 H 0.520(9) 0.626(2) 0.702(3) 0.110(12) Uiso 1 1 d . . . H1A H 0.900(6) 0.9861(15) 0.699(2) 0.058(7) Uiso 1 1 d . . . H1B H 0.694(6) 1.0213(17) 0.576(2) 0.082(9) Uiso 1 1 d . . . N1 N 0.7619(6) 0.98094(11) 0.63039(18) 0.0515(6) Uani 1 1 d . . . N2 N 0.9505(4) 0.86539(10) 0.77203(14) 0.0358(5) Uani 1 1 d . . . N3 N 0.6972(4) 0.71731(10) 0.73024(13) 0.0366(5) Uani 1 1 d . . . O1 O 0.4825(5) 0.89487(9) 0.51511(13) 0.0566(5) Uani 1 1 d . . . O2 O 0.4153(4) 0.57822(8) 0.67920(12) 0.0435(4) Uani 1 1 d . . . O3 O 0.1430(4) 0.64076(8) 0.53883(12) 0.0460(5) 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 0.0512(12) 0.0301(11) 0.0344(12) -0.0014(10) -0.0071(10) 0.0005(9) C2 0.0371(10) 0.0301(10) 0.0287(10) -0.0031(10) -0.0019(8) 0.0011(8) C3 0.0444(11) 0.0388(12) 0.0277(11) -0.0007(10) -0.0068(9) -0.0019(9) C4 0.0470(11) 0.0354(11) 0.0329(12) 0.0030(10) -0.0033(9) -0.0009(10) C5 0.0427(11) 0.0308(11) 0.0299(11) -0.0038(10) -0.0055(9) -0.0009(9) C6 0.0341(10) 0.0311(11) 0.0299(11) -0.0019(10) -0.0020(8) -0.0006(9) C7 0.0398(11) 0.0259(10) 0.0347(11) 0.0015(10) -0.0050(9) -0.0024(9) N1 0.0807(14) 0.0281(10) 0.0402(12) 0.0019(10) -0.0213(11) -0.0039(10) N2 0.0413(9) 0.0316(9) 0.0328(10) -0.0020(8) -0.0049(7) -0.0003(7) N3 0.0452(10) 0.0302(9) 0.0331(10) 0.0008(8) -0.0033(8) -0.0029(7) O1 0.0911(12) 0.0340(9) 0.0382(10) -0.0003(8) -0.0249(9) -0.0006(8) O2 0.0598(9) 0.0301(8) 0.0359(9) 0.0025(7) -0.0184(7) -0.0057(7) O3 0.0605(10) 0.0299(8) 0.0434(9) 0.0062(7) -0.0161(7) -0.0034(7) _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(2) . ? C1 N1 1.325(3) . ? C1 C2 1.492(3) . ? C2 N2 1.339(2) . ? C2 C5 1.385(3) . ? C3 N2 1.321(3) . ? C3 C4 1.387(3) . ? C3 H3 0.9300 . ? C4 N3 1.329(3) . ? C4 H4 0.9300 . ? C5 N3 1.330(2) . ? C5 H5 0.9300 . ? C6 O3 1.207(2) . ? C6 O2 1.323(2) . ? C6 C7 1.476(3) . ? C7 C7 1.311(4) 3_566 ? C7 H7 0.9300 . ? N1 H1A 0.97(2) . ? N1 H1B 0.99(3) . ? O2 H2 0.94(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 N1 124.4(2) . . ? O1 C1 C2 119.62(19) . . ? N1 C1 C2 115.98(19) . . ? N2 C2 C5 121.00(19) . . ? N2 C2 C1 119.14(18) . . ? C5 C2 C1 119.85(18) . . ? N2 C3 C4 121.81(19) . . ? N2 C3 H3 119.1 . . ? C4 C3 H3 119.1 . . ? N3 C4 C3 121.1(2) . . ? N3 C4 H4 119.4 . . ? C3 C4 H4 119.4 . . ? N3 C5 C2 121.53(19) . . ? N3 C5 H5 119.2 . . ? C2 C5 H5 119.2 . . ? O3 C6 O2 123.40(18) . . ? O3 C6 C7 123.50(18) . . ? O2 C6 C7 113.08(17) . . ? C7 C7 C6 122.5(2) 3_566 . ? C7 C7 H7 118.8 3_566 . ? C6 C7 H7 118.8 . . ? C1 N1 H1A 116.9(16) . . ? C1 N1 H1B 114.1(15) . . ? H1A N1 H1B 129(2) . . ? C3 N2 C2 117.17(18) . . ? C4 N3 C5 117.34(18) . . ? C6 O2 H2 115(2) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 26.36 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.199 _refine_diff_density_min -0.210 _refine_diff_density_rms 0.049 # Attachment '- PZA-SA.cif' data_2PZA-1SA _database_code_depnum_ccdc_archive 'CCDC 849831' #TrackingRef '- PZA-SA.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C7 H8 N3 O3' _chemical_formula_weight 182.16 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 3.8701(4) _cell_length_b 17.3536(18) _cell_length_c 12.4978(13) _cell_angle_alpha 90.00 _cell_angle_beta 95.859(2) _cell_angle_gamma 90.00 _cell_volume 834.97(15) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2392 _cell_measurement_theta_min 2.86 _cell_measurement_theta_max 24.43 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.449 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 380 _exptl_absorpt_coefficient_mu 0.116 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.9639 _exptl_absorpt_correction_T_max 0.9795 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 8467 _diffrn_reflns_av_R_equivalents 0.0335 _diffrn_reflns_av_sigmaI/netI 0.0231 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.02 _diffrn_reflns_theta_max 26.09 _reflns_number_total 1655 _reflns_number_gt 1433 _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 ; 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^)+(0.0548P)^2^+0.1684P] 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 1655 _refine_ls_number_parameters 130 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0502 _refine_ls_R_factor_gt 0.0424 _refine_ls_wR_factor_ref 0.1081 _refine_ls_wR_factor_gt 0.1038 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _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 0.3493(5) 0.58943(9) 0.89907(12) 0.0426(4) Uani 1 1 d . . . C2 C 0.2517(4) 0.65235(8) 0.81892(11) 0.0352(4) Uani 1 1 d . . . C3 C -0.0177(4) 0.69084(9) 0.65860(12) 0.0409(4) Uani 1 1 d . . . H3 H -0.1573 0.6807 0.5951 0.049 Uiso 1 1 calc R . . C4 C 0.1097(4) 0.76458(9) 0.67738(12) 0.0412(4) Uani 1 1 d . . . H4 H 0.0560 0.8026 0.6259 0.049 Uiso 1 1 calc R . . C5 C 0.3757(4) 0.72618(8) 0.83847(12) 0.0381(4) Uani 1 1 d . . . H5 H 0.5101 0.7368 0.9028 0.046 Uiso 1 1 calc R . . C6 C 0.7860(4) 0.92083(8) 0.90773(11) 0.0334(3) Uani 1 1 d . . . C7 C 0.9097(4) 0.99969(8) 0.94353(11) 0.0353(4) Uani 1 1 d . . . H7B H 0.7123 1.0344 0.9399 0.042 Uiso 1 1 calc R . . H7A H 1.0685 1.0188 0.8944 0.042 Uiso 1 1 calc R . . H2 H 0.498(6) 0.8758(14) 0.7955(17) 0.072(6) Uiso 1 1 d . . . H1A H 0.101(5) 0.5150(11) 0.8095(16) 0.052(5) Uiso 1 1 d . . . H1B H 0.296(6) 0.4783(14) 0.9205(18) 0.077(7) Uiso 1 1 d . . . N1 N 0.2388(5) 0.51965(8) 0.87172(13) 0.0544(5) Uani 1 1 d . . . N2 N 0.0538(4) 0.63420(7) 0.72870(10) 0.0390(3) Uani 1 1 d . . . N3 N 0.3070(3) 0.78245(7) 0.76731(10) 0.0403(3) Uani 1 1 d . . . O1 O 0.5278(4) 0.60536(7) 0.98333(10) 0.0630(4) Uani 1 1 d . . . O2 O 0.5848(3) 0.92236(6) 0.81599(9) 0.0491(3) Uani 1 1 d . . . O3 O 0.8572(3) 0.86258(6) 0.95692(9) 0.0502(4) 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 0.0618(10) 0.0305(8) 0.0329(8) -0.0026(6) -0.0083(7) 0.0004(7) C2 0.0442(8) 0.0294(7) 0.0311(7) -0.0034(6) -0.0014(6) 0.0001(6) C3 0.0505(9) 0.0376(8) 0.0323(8) -0.0018(6) -0.0073(7) 0.0003(7) C4 0.0551(10) 0.0333(8) 0.0335(8) 0.0034(6) -0.0040(7) 0.0017(7) C5 0.0498(9) 0.0310(8) 0.0312(8) -0.0025(6) -0.0065(6) -0.0009(6) C6 0.0361(8) 0.0296(7) 0.0333(7) 0.0009(6) -0.0019(6) 0.0004(6) C7 0.0370(8) 0.0294(8) 0.0380(8) 0.0019(6) -0.0034(6) -0.0037(6) N1 0.0858(12) 0.0296(7) 0.0420(8) 0.0023(6) -0.0213(8) -0.0044(7) N2 0.0506(8) 0.0315(7) 0.0328(7) -0.0013(5) -0.0056(6) -0.0017(5) N3 0.0522(8) 0.0291(7) 0.0381(7) 0.0003(5) -0.0018(6) -0.0028(6) O1 0.1045(11) 0.0344(7) 0.0424(7) -0.0008(5) -0.0302(7) -0.0024(6) O2 0.0693(8) 0.0286(6) 0.0438(6) 0.0023(5) -0.0216(6) -0.0072(5) O3 0.0687(8) 0.0299(6) 0.0472(7) 0.0055(5) -0.0169(6) -0.0031(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.2305(18) . ? C1 N1 1.318(2) . ? C1 C2 1.504(2) . ? C2 N2 1.3346(19) . ? C2 C5 1.381(2) . ? C3 N2 1.327(2) . ? C3 C4 1.383(2) . ? C3 H3 0.9300 . ? C4 N3 1.3295(19) . ? C4 H4 0.9300 . ? C5 N3 1.3292(19) . ? C5 H5 0.9300 . ? C6 O3 1.2004(17) . ? C6 O2 1.3188(18) . ? C6 C7 1.503(2) . ? C7 C7 1.510(3) 3_777 ? C7 H7B 0.9700 . ? C7 H7A 0.9700 . ? N1 H1A 0.901(19) . ? N1 H1B 0.95(2) . ? O2 H2 0.90(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 O1 C1 N1 124.57(15) . . ? O1 C1 C2 119.20(13) . . ? N1 C1 C2 116.22(13) . . ? N2 C2 C5 121.83(13) . . ? N2 C2 C1 118.36(13) . . ? C5 C2 C1 119.78(13) . . ? N2 C3 C4 121.79(14) . . ? N2 C3 H3 119.1 . . ? C4 C3 H3 119.1 . . ? N3 C4 C3 121.56(14) . . ? N3 C4 H4 119.2 . . ? C3 C4 H4 119.2 . . ? N3 C5 C2 121.40(14) . . ? N3 C5 H5 119.3 . . ? C2 C5 H5 119.3 . . ? O3 C6 O2 123.13(13) . . ? O3 C6 C7 124.39(13) . . ? O2 C6 C7 112.48(12) . . ? C6 C7 C7 112.82(15) . 3_777 ? C6 C7 H7B 109.0 . . ? C7 C7 H7B 109.0 3_777 . ? C6 C7 H7A 109.0 . . ? C7 C7 H7A 109.0 3_777 . ? H7B C7 H7A 107.8 . . ? C1 N1 H1A 117.1(13) . . ? C1 N1 H1B 118.6(13) . . ? H1A N1 H1B 124.2(19) . . ? C3 N2 C2 116.49(13) . . ? C5 N3 C4 116.92(13) . . ? C6 O2 H2 113.5(14) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.09 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.149 _refine_diff_density_min -0.214 _refine_diff_density_rms 0.050