# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'A. Nangia' _publ_contact_author_address ; School of Chemistry University of Hyderabad P O Central University Hyderabad 500046 Hyderabad 500 046 INDIA ; _publ_contact_author_email 'ASHWINI NANGIA@REDIFFMAIL.COM' _publ_section_title ; Carboxamide pyridine N-oxide heterosynthon for crystal engineering and pharmaceutical cocrystals ; loop_ _publ_author_name 'A. Nangia' 'N. Jagadeesh Babu' 'L. Sreenivas Reddy' data_pbca_1 _database_code_depnum_ccdc_archive 'CCDC 288479' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Hydrate of 1:1 complex of barbituric acid and bipyridine-bis-N-oxide ; _chemical_name_common ;Hydrate of 1:1 complex of barbituric acid and bipyridine-bis- N-oxide ; _chemical_melting_point ? _chemical_formula_moiety 'C10 H8 N2 O2, C4 H4 N2 O3, H2 O' _chemical_formula_sum 'C14 H14 N4 O6' _chemical_formula_weight 334.29 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'Pbca ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 16.2210(11) _cell_length_b 6.5971(5) _cell_length_c 27.0692(19) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2896.7(4) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4953 _cell_measurement_theta_min 2.51 _cell_measurement_theta_max 26.02 _exptl_crystal_description Plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.533 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1392 _exptl_absorpt_coefficient_mu 0.122 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9481 _exptl_absorpt_correction_T_max 0.9915 _exptl_absorpt_process_details 'Bruker AXS SADABS program' _exptl_special_details ; Sheldrick,G.M.,(2003),University of gottingen,Germany ; _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 17132 _diffrn_reflns_av_R_equivalents 0.0526 _diffrn_reflns_av_sigmaI/netI 0.0346 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 1.50 _diffrn_reflns_theta_max 26.03 _reflns_number_total 2844 _reflns_number_gt 2270 _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 ? _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^)+(0.0556P)^2^+1.4301P] 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 2844 _refine_ls_number_parameters 233 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0682 _refine_ls_R_factor_gt 0.0510 _refine_ls_wR_factor_ref 0.1204 _refine_ls_wR_factor_gt 0.1125 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.074 _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 O1 O 0.07721(9) 0.0317(2) 0.74366(5) 0.0223(4) Uani 1 1 d . . . O2 O 0.58365(9) -0.0324(3) 0.55597(6) 0.0300(4) Uani 1 1 d . . . O3 O 0.24155(9) 0.9049(2) 0.85397(5) 0.0208(4) Uani 1 1 d . . . O4 O 0.49697(9) 0.9854(2) 0.91854(6) 0.0252(4) Uani 1 1 d . . . O5 O 0.26130(9) 1.1226(2) 1.01208(5) 0.0210(4) Uani 1 1 d . . . O6 O 0.06481(10) 0.1121(3) 0.29380(6) 0.0217(4) Uani 1 1 d . . . H6B H 0.0685(17) 0.231(5) 0.2798(10) 0.053(9) Uiso 1 1 d . . . H6A H 0.0160(18) 0.062(4) 0.2851(10) 0.038(8) Uiso 1 1 d . . . N1 N 0.14702(10) 0.0268(3) 0.71831(6) 0.0156(4) Uani 1 1 d . . . N2 N 0.51652(10) -0.0170(3) 0.58313(6) 0.0199(4) Uani 1 1 d . . . N3 N 0.37005(10) 0.9449(3) 0.88629(6) 0.0178(4) Uani 1 1 d . . . H3 H 0.3915(15) 0.928(4) 0.8553(9) 0.031(7) Uiso 1 1 d . . . N4 N 0.25146(11) 1.0075(3) 0.93359(6) 0.0169(4) Uani 1 1 d . . . H4 H 0.2010(15) 1.011(3) 0.9332(8) 0.018(6) Uiso 1 1 d . . . C1 C 0.21934(12) 0.0445(3) 0.74266(7) 0.0165(4) Uani 1 1 d . . . H1 H 0.2194 0.0615 0.7775 0.020 Uiso 1 1 calc R . . C2 C 0.29284(12) 0.0382(3) 0.71751(7) 0.0154(4) Uani 1 1 d . . . H2 H 0.3432 0.0505 0.7351 0.018 Uiso 1 1 calc R . . C3 C 0.29421(12) 0.0137(3) 0.66614(7) 0.0140(4) Uani 1 1 d . . . C4 C 0.21776(12) -0.0030(3) 0.64242(7) 0.0152(4) Uani 1 1 d . . . H4A H 0.2160 -0.0200 0.6076 0.018 Uiso 1 1 calc R . . C5 C 0.14550(13) 0.0046(3) 0.66845(8) 0.0167(5) Uani 1 1 d . . . H5 H 0.0943 -0.0057 0.6516 0.020 Uiso 1 1 calc R . . C6 C 0.37224(12) 0.0058(3) 0.63802(7) 0.0141(4) Uani 1 1 d . . . C7 C 0.44788(12) -0.0370(3) 0.66009(8) 0.0181(5) Uani 1 1 d . . . H7 H 0.4505 -0.0590 0.6947 0.022 Uiso 1 1 calc R . . C8 C 0.51894(12) -0.0480(3) 0.63239(8) 0.0199(5) Uani 1 1 d . . . H8 H 0.5700 -0.0776 0.6480 0.024 Uiso 1 1 calc R . . C9 C 0.44407(12) 0.0271(3) 0.56071(8) 0.0205(5) Uani 1 1 d . . . H9 H 0.4430 0.0493 0.5260 0.025 Uiso 1 1 calc R . . C10 C 0.37271(12) 0.0402(3) 0.58714(8) 0.0179(5) Uani 1 1 d . . . H10 H 0.3227 0.0731 0.5707 0.021 Uiso 1 1 calc R . . C11 C 0.42280(13) 0.9769(3) 0.92488(8) 0.0189(5) Uani 1 1 d . . . C12 C 0.38391(12) 0.9894(4) 0.97509(8) 0.0200(5) Uani 1 1 d . . . H12A H 0.4154 1.0883 0.9951 0.024 Uiso 1 1 calc R . . H12B H 0.3894 0.8555 0.9913 0.024 Uiso 1 1 calc R . . C13 C 0.29458(12) 1.0494(3) 0.97614(7) 0.0160(4) Uani 1 1 d . . . C14 C 0.28481(12) 0.9482(3) 0.88892(7) 0.0155(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 O1 0.0111(8) 0.0307(9) 0.0252(8) -0.0048(7) 0.0069(6) -0.0019(6) O2 0.0096(7) 0.0601(12) 0.0202(8) -0.0059(8) 0.0043(6) -0.0024(7) O3 0.0195(8) 0.0258(9) 0.0170(7) 0.0001(6) -0.0030(6) -0.0026(6) O4 0.0132(8) 0.0365(10) 0.0260(9) -0.0020(7) 0.0007(6) 0.0008(7) O5 0.0202(8) 0.0251(9) 0.0177(7) -0.0010(6) 0.0028(6) -0.0006(6) O6 0.0155(8) 0.0307(10) 0.0190(8) 0.0033(7) -0.0014(6) -0.0017(7) N1 0.0121(8) 0.0153(10) 0.0194(9) 0.0001(7) 0.0014(7) -0.0003(7) N2 0.0123(9) 0.0287(11) 0.0186(9) -0.0043(8) 0.0025(7) -0.0029(7) N3 0.0148(9) 0.0257(11) 0.0130(9) -0.0003(7) 0.0013(7) 0.0003(7) N4 0.0102(9) 0.0224(10) 0.0180(9) 0.0010(7) 0.0008(7) 0.0000(7) C1 0.0172(10) 0.0161(11) 0.0163(10) 0.0002(8) -0.0017(8) -0.0002(8) C2 0.0132(10) 0.0144(11) 0.0186(10) 0.0008(8) -0.0018(8) 0.0009(8) C3 0.0141(10) 0.0102(10) 0.0176(10) 0.0014(8) -0.0003(8) 0.0000(8) C4 0.0175(10) 0.0132(11) 0.0148(10) 0.0004(8) -0.0007(8) -0.0002(8) C5 0.0142(10) 0.0152(11) 0.0208(11) -0.0014(8) -0.0042(8) 0.0001(8) C6 0.0152(10) 0.0109(10) 0.0163(10) -0.0022(8) 0.0002(8) -0.0027(8) C7 0.0166(11) 0.0223(12) 0.0153(10) -0.0007(8) -0.0007(8) -0.0012(9) C8 0.0137(10) 0.0267(13) 0.0193(11) -0.0010(9) -0.0040(8) -0.0001(9) C9 0.0170(11) 0.0308(13) 0.0138(10) -0.0001(9) -0.0019(8) -0.0020(9) C10 0.0137(10) 0.0212(12) 0.0188(11) -0.0013(8) -0.0018(8) -0.0005(9) C11 0.0171(11) 0.0192(12) 0.0204(11) 0.0002(9) -0.0008(9) 0.0011(8) C12 0.0160(11) 0.0279(13) 0.0162(11) -0.0006(9) -0.0037(8) -0.0011(9) C13 0.0170(10) 0.0164(11) 0.0147(10) 0.0027(8) 0.0009(8) -0.0029(8) C14 0.0157(10) 0.0152(11) 0.0155(10) 0.0031(8) -0.0006(8) 0.0006(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 N1 1.325(2) . ? O2 N2 1.318(2) . ? O3 C14 1.212(2) . ? O4 C11 1.217(2) . ? O5 C13 1.213(2) . ? O6 H6B 0.87(3) . ? O6 H6A 0.89(3) . ? N1 C1 1.351(3) . ? N1 C5 1.358(3) . ? N2 C8 1.350(3) . ? N2 C9 1.354(3) . ? N3 C11 1.367(3) . ? N3 C14 1.385(3) . ? N3 H3 0.92(3) . ? N4 C13 1.376(3) . ? N4 C14 1.381(3) . ? N4 H4 0.82(2) . ? C1 C2 1.373(3) . ? C1 H1 0.9500 . ? C2 C3 1.400(3) . ? C2 H2 0.9500 . ? C3 C4 1.401(3) . ? C3 C6 1.478(3) . ? C4 C5 1.369(3) . ? C4 H4A 0.9500 . ? C5 H5 0.9500 . ? C6 C7 1.394(3) . ? C6 C10 1.396(3) . ? C7 C8 1.377(3) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? C9 C10 1.364(3) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? C11 C12 1.500(3) . ? C12 C13 1.502(3) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? 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 H6B O6 H6A 106(2) . . ? O1 N1 C1 119.19(16) . . ? O1 N1 C5 120.14(16) . . ? C1 N1 C5 120.67(17) . . ? O2 N2 C8 121.03(17) . . ? O2 N2 C9 118.92(17) . . ? C8 N2 C9 120.04(18) . . ? C11 N3 C14 125.69(18) . . ? C11 N3 H3 118.7(16) . . ? C14 N3 H3 115.4(16) . . ? C13 N4 C14 126.20(18) . . ? C13 N4 H4 120.8(16) . . ? C14 N4 H4 112.9(16) . . ? N1 C1 C2 120.64(18) . . ? N1 C1 H1 119.7 . . ? C2 C1 H1 119.7 . . ? C1 C2 C3 120.63(19) . . ? C1 C2 H2 119.7 . . ? C3 C2 H2 119.7 . . ? C2 C3 C4 116.76(18) . . ? C2 C3 C6 121.96(18) . . ? C4 C3 C6 121.28(17) . . ? C5 C4 C3 121.28(18) . . ? C5 C4 H4A 119.4 . . ? C3 C4 H4A 119.4 . . ? N1 C5 C4 120.02(19) . . ? N1 C5 H5 120.0 . . ? C4 C5 H5 120.0 . . ? C7 C6 C10 116.82(18) . . ? C7 C6 C3 122.70(18) . . ? C10 C6 C3 120.48(18) . . ? C8 C7 C6 120.94(19) . . ? C8 C7 H7 119.5 . . ? C6 C7 H7 119.5 . . ? N2 C8 C7 120.37(19) . . ? N2 C8 H8 119.8 . . ? C7 C8 H8 119.8 . . ? N2 C9 C10 121.00(19) . . ? N2 C9 H9 119.5 . . ? C10 C9 H9 119.5 . . ? C9 C10 C6 120.80(19) . . ? C9 C10 H10 119.6 . . ? C6 C10 H10 119.6 . . ? O4 C11 N3 121.23(19) . . ? O4 C11 C12 122.75(19) . . ? N3 C11 C12 115.95(18) . . ? C11 C12 C13 115.91(17) . . ? C11 C12 H12A 108.3 . . ? C13 C12 H12A 108.3 . . ? C11 C12 H12B 108.3 . . ? C13 C12 H12B 108.3 . . ? H12A C12 H12B 107.4 . . ? O5 C13 N4 121.68(19) . . ? O5 C13 C12 123.32(18) . . ? N4 C13 C12 114.94(18) . . ? O3 C14 N4 121.55(19) . . ? O3 C14 N3 122.30(19) . . ? N4 C14 N3 116.14(18) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 26.03 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.252 _refine_diff_density_min -0.300 _refine_diff_density_rms 0.075 # Attachment 'Isonic Noxide 1.cif' data_a _database_code_depnum_ccdc_archive 'CCDC 288480' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Isonicotinamide-N-oxide ; _chemical_name_common Isonicotinamide-N-oxide _chemical_melting_point ? _chemical_formula_moiety 'C6 H6 N2 O2' _chemical_formula_sum 'C6 H6 N2 O2' _chemical_formula_weight 138.13 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P n a 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z+1/2' _cell_length_a 13.467(3) _cell_length_b 11.722(3) _cell_length_c 3.7370(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 589.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 619 _cell_measurement_theta_min 3.03 _cell_measurement_theta_max 25.79 _exptl_crystal_description needle _exptl_crystal_colour orange _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.555 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 288 _exptl_absorpt_coefficient_mu 0.120 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9592 _exptl_absorpt_correction_T_max 0.9928 _exptl_absorpt_process_details 'Bruker AXS SADABS program' _exptl_special_details ; Sheldrick, G. M.,(2003) University of gottingen, Germany ; _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 1988 _diffrn_reflns_av_R_equivalents 0.0340 _diffrn_reflns_av_sigmaI/netI 0.0403 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -4 _diffrn_reflns_limit_l_max 4 _diffrn_reflns_theta_min 2.30 _diffrn_reflns_theta_max 26.03 _reflns_number_total 679 _reflns_number_gt 625 _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 ? _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^)+(0.0422P)^2^+1.2159P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0(10) _refine_ls_number_reflns 679 _refine_ls_number_parameters 99 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0738 _refine_ls_R_factor_gt 0.0687 _refine_ls_wR_factor_ref 0.1384 _refine_ls_wR_factor_gt 0.1363 _refine_ls_goodness_of_fit_ref 1.201 _refine_ls_restrained_S_all 1.199 _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 O1 O 0.3416(2) 0.5345(3) 0.2867(12) 0.0176(9) Uani 1 1 d . . . O2 O -0.0551(2) 0.6835(3) 1.0129(13) 0.0200(10) Uani 1 1 d . . . N1 N 0.2668(3) 0.5855(3) 0.4447(13) 0.0129(10) Uani 1 1 d . . . N2 N 0.0138(3) 0.8581(3) 0.9760(15) 0.0167(10) Uani 1 1 d . . . C1 C 0.2662(3) 0.7015(4) 0.4838(17) 0.0130(10) Uani 1 1 d . . . H1 H 0.3219 0.7449 0.4076 0.016 Uiso 1 1 calc R . . C2 C 0.1865(3) 0.7550(4) 0.6309(15) 0.0120(11) Uani 1 1 d . . . H2 H 0.1863 0.8359 0.6479 0.014 Uiso 1 1 calc R . . C3 C 0.1060(4) 0.6942(4) 0.7560(17) 0.0143(11) Uani 1 1 d . . . C4 C 0.1093(3) 0.5755(4) 0.7281(17) 0.0138(12) Uani 1 1 d . . . H4 H 0.0560 0.5308 0.8175 0.017 Uiso 1 1 calc R . . C5 C 0.1892(4) 0.5237(4) 0.5726(16) 0.0174(13) Uani 1 1 d . . . H5 H 0.1905 0.4429 0.5534 0.021 Uiso 1 1 calc R . . C6 C 0.0140(3) 0.7455(4) 0.9270(16) 0.0145(12) Uani 1 1 d . . . H2A H -0.041(4) 0.890(4) 1.041(14) 0.005(13) Uiso 1 1 d . . . H2B H 0.064(5) 0.898(5) 0.93(2) 0.04(2) 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 0.0061(15) 0.0171(18) 0.030(2) -0.001(2) 0.0027(18) 0.0059(14) O2 0.0093(16) 0.0137(16) 0.037(3) -0.007(2) 0.008(2) -0.0013(13) N1 0.0110(19) 0.012(2) 0.016(2) 0.000(2) -0.002(2) 0.0004(16) N2 0.011(2) 0.0090(19) 0.030(3) 0.004(2) 0.010(2) 0.0039(18) C1 0.012(2) 0.011(2) 0.016(3) -0.001(2) -0.003(3) -0.0053(18) C2 0.013(2) 0.009(2) 0.014(3) -0.004(2) -0.001(2) -0.0001(19) C3 0.015(2) 0.016(2) 0.012(2) 0.003(2) -0.001(2) -0.0011(19) C4 0.005(2) 0.013(2) 0.023(3) -0.001(3) -0.003(2) -0.0033(18) C5 0.012(2) 0.010(2) 0.029(4) -0.001(2) -0.002(2) 0.001(2) C6 0.007(2) 0.017(2) 0.020(3) -0.002(2) -0.004(2) 0.0033(19) _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 N1 1.311(5) . ? O2 C6 1.223(6) . ? N1 C5 1.359(6) . ? N1 C1 1.367(6) . ? N2 C6 1.333(6) . ? N2 H2A 0.86(5) . ? N2 H2B 0.84(6) . ? C1 C2 1.360(7) . ? C1 H1 0.9500 . ? C2 C3 1.380(7) . ? C2 H2 0.9500 . ? C3 C4 1.395(6) . ? C3 C6 1.518(7) . ? C4 C5 1.365(7) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? 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 N1 C5 120.4(4) . . ? O1 N1 C1 120.4(4) . . ? C5 N1 C1 119.2(4) . . ? C6 N2 H2A 118(3) . . ? C6 N2 H2B 121(4) . . ? H2A N2 H2B 120(5) . . ? C2 C1 N1 120.5(4) . . ? C2 C1 H1 119.8 . . ? N1 C1 H1 119.8 . . ? C1 C2 C3 121.2(4) . . ? C1 C2 H2 119.4 . . ? C3 C2 H2 119.4 . . ? C2 C3 C4 117.7(5) . . ? C2 C3 C6 125.4(4) . . ? C4 C3 C6 116.9(4) . . ? C5 C4 C3 120.1(5) . . ? C5 C4 H4 120.0 . . ? C3 C4 H4 120.0 . . ? N1 C5 C4 121.2(4) . . ? N1 C5 H5 119.4 . . ? C4 C5 H5 119.4 . . ? O2 C6 N2 123.3(5) . . ? O2 C6 C3 119.8(4) . . ? N2 C6 C3 116.9(4) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.03 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.274 _refine_diff_density_min -0.398 _refine_diff_density_rms 0.073 # Attachment 'Nicotin Noxide 2.cif' data_an172_m _database_code_depnum_ccdc_archive 'CCDC 288481' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Nicotinamide-N-oxide ; _chemical_name_common Nicotinamide-N-oxide _chemical_melting_point ? _chemical_formula_moiety 'C6 H6 N2 O2' _chemical_formula_sum 'C6 H6 N2 O2' _chemical_formula_weight 138.13 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 'P 2(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 11.0498(16) _cell_length_b 3.6869(5) _cell_length_c 15.019(2) _cell_angle_alpha 90.00 _cell_angle_beta 110.064(2) _cell_angle_gamma 90.00 _cell_volume 574.73(14) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2513 _cell_measurement_theta_min 2.81 _cell_measurement_theta_max 26.01 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.596 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 288 _exptl_absorpt_coefficient_mu 0.123 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9512 _exptl_absorpt_correction_T_max 0.9758 _exptl_absorpt_process_details 'Bruker AXS SADABS program' _exptl_special_details ; Sheldrick,G.M.,(2003),University of gottingen,Germany ; _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 3173 _diffrn_reflns_av_R_equivalents 0.0157 _diffrn_reflns_av_sigmaI/netI 0.0172 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.00 _diffrn_reflns_theta_max 26.01 _reflns_number_total 1136 _reflns_number_gt 1061 _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 ? _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^)+(0.0620P)^2^+0.2429P] 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 1136 _refine_ls_number_parameters 99 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0398 _refine_ls_R_factor_gt 0.0379 _refine_ls_wR_factor_ref 0.1028 _refine_ls_wR_factor_gt 0.1008 _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_restrained_S_all 1.069 _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 O1 O 0.83405(8) 0.1772(3) 0.41406(6) 0.0175(3) Uani 1 1 d . . . O2 O 0.96974(9) 0.4772(3) 0.81746(7) 0.0223(3) Uani 1 1 d . . . N1 N 0.81448(10) 0.3369(3) 0.48683(7) 0.0142(3) Uani 1 1 d . . . N2 N 1.11802(10) 0.5131(3) 0.74468(8) 0.0179(3) Uani 1 1 d . . . H2A H 1.1792(17) 0.492(4) 0.7986(13) 0.021(4) Uiso 1 1 d . . . H2B H 1.1345(16) 0.556(5) 0.6926(13) 0.024(4) Uiso 1 1 d . . . C1 C 0.91154(11) 0.3470(3) 0.57134(9) 0.0142(3) Uani 1 1 d . . . H1 H 0.9934 0.2492 0.5770 0.017 Uiso 1 1 calc R . . C2 C 0.89226(11) 0.4989(3) 0.64948(9) 0.0141(3) Uani 1 1 d . . . C3 C 0.77214(12) 0.6410(3) 0.64118(9) 0.0157(3) Uani 1 1 d . . . H3 H 0.7567 0.7399 0.6947 0.019 Uiso 1 1 calc R . . C4 C 0.67556(12) 0.6353(4) 0.55317(9) 0.0167(3) Uani 1 1 d . . . H4 H 0.5937 0.7373 0.5457 0.020 Uiso 1 1 calc R . . C5 C 0.69750(12) 0.4829(3) 0.47662(9) 0.0161(3) Uani 1 1 d . . . H5 H 0.6308 0.4795 0.4165 0.019 Uiso 1 1 calc R . . C6 C 0.99776(12) 0.4969(3) 0.74525(9) 0.0154(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 O1 0.0178(5) 0.0229(5) 0.0130(5) -0.0035(4) 0.0069(3) -0.0006(4) O2 0.0192(5) 0.0341(6) 0.0145(5) 0.0023(4) 0.0067(4) -0.0008(4) N1 0.0153(5) 0.0145(5) 0.0141(5) -0.0001(4) 0.0065(4) -0.0017(4) N2 0.0144(5) 0.0266(7) 0.0118(6) 0.0023(4) 0.0033(4) -0.0004(4) C1 0.0125(5) 0.0135(6) 0.0163(6) 0.0021(5) 0.0045(5) -0.0010(5) C2 0.0149(6) 0.0121(6) 0.0160(7) 0.0016(5) 0.0061(5) -0.0023(4) C3 0.0182(6) 0.0129(6) 0.0182(6) 0.0004(5) 0.0090(5) -0.0012(5) C4 0.0137(6) 0.0150(6) 0.0223(7) 0.0015(5) 0.0074(5) 0.0005(5) C5 0.0134(6) 0.0164(6) 0.0174(6) 0.0019(5) 0.0036(5) -0.0006(4) C6 0.0169(6) 0.0137(6) 0.0158(7) 0.0004(5) 0.0058(5) -0.0004(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 O1 N1 1.3230(14) . ? O2 C6 1.2279(16) . ? N1 C1 1.3522(16) . ? N1 C5 1.3594(16) . ? N2 C6 1.3332(17) . ? N2 H2A 0.862(19) . ? N2 H2B 0.876(18) . ? C1 C2 1.3813(18) . ? C1 H1 0.9500 . ? C2 C3 1.3922(18) . ? C2 C6 1.5091(17) . ? C3 C4 1.3851(18) . ? C3 H3 0.9500 . ? C4 C5 1.3739(18) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? 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 N1 C1 119.07(10) . . ? O1 N1 C5 120.10(10) . . ? C1 N1 C5 120.82(11) . . ? C6 N2 H2A 116.8(11) . . ? C6 N2 H2B 121.8(11) . . ? H2A N2 H2B 121.3(15) . . ? N1 C1 C2 120.32(11) . . ? N1 C1 H1 119.8 . . ? C2 C1 H1 119.8 . . ? C1 C2 C3 119.78(11) . . ? C1 C2 C6 120.92(11) . . ? C3 C2 C6 119.23(11) . . ? C4 C3 C2 118.58(12) . . ? C4 C3 H3 120.7 . . ? C2 C3 H3 120.7 . . ? C5 C4 C3 120.36(11) . . ? C5 C4 H4 119.8 . . ? C3 C4 H4 119.8 . . ? N1 C5 C4 120.09(11) . . ? N1 C5 H5 120.0 . . ? C4 C5 H5 120.0 . . ? O2 C6 N2 124.21(11) . . ? O2 C6 C2 119.71(11) . . ? N2 C6 C2 116.07(11) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.01 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.209 _refine_diff_density_min -0.351 _refine_diff_density_rms 0.070 # Attachment 'Phenobarb 5 BPNO.cif' data_an389 _database_code_depnum_ccdc_archive 'CCDC 288482' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1:0.5 complex of phenobarbital and bipyridine-bis-N-oxide ; _chemical_name_common '1:0.5 complex of phenobarbital and bipyridine-bis-N-oxide' _chemical_melting_point ? _chemical_formula_moiety 'C12 H12 N2 O3, 0.5(C10 H8 N2 O2)' _chemical_formula_sum 'C17 H16 N3 O4' _chemical_formula_weight 326.33 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 '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)/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.3768(12) _cell_length_b 15.8728(18) _cell_length_c 9.4522(11) _cell_angle_alpha 90.00 _cell_angle_beta 93.165(2) _cell_angle_gamma 90.00 _cell_volume 1554.5(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3670 _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 26.04 _exptl_crystal_description Hexagonal _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.394 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 684 _exptl_absorpt_coefficient_mu 0.101 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9702 _exptl_absorpt_correction_T_max 0.9889 _exptl_absorpt_process_details 'Bruker AXS SADABS program' _exptl_special_details ; Sheldrick,G.M.,(2003),University of gottingen,Germany ; _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 7009 _diffrn_reflns_av_R_equivalents 0.0314 _diffrn_reflns_av_sigmaI/netI 0.0437 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.97 _diffrn_reflns_theta_max 26.04 _reflns_number_total 3072 _reflns_number_gt 2463 _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 ? _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^)+(0.0577P)^2^+0.4887P] 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 3072 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0595 _refine_ls_R_factor_gt 0.0458 _refine_ls_wR_factor_ref 0.1154 _refine_ls_wR_factor_gt 0.1078 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.021 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.44225(10) 0.90824(7) 0.08615(13) 0.0203(3) Uani 1 1 d . . . O2 O 0.71929(12) 0.71389(8) 0.65012(13) 0.0265(3) Uani 1 1 d . . . O3 O 0.38684(11) 0.76098(8) 0.33347(13) 0.0253(3) Uani 1 1 d . . . O4 O 0.70748(11) 0.95308(8) 0.35298(13) 0.0237(3) Uani 1 1 d . . . N1 N 0.32029(13) 0.93152(9) 0.06057(14) 0.0170(3) Uani 1 1 d . . . N2 N 0.55494(14) 0.73885(9) 0.49106(15) 0.0196(3) Uani 1 1 d . . . H2 H 0.5168(19) 0.6880(13) 0.516(2) 0.028(5) Uiso 1 1 d . . . N3 N 0.54269(14) 0.86106(9) 0.35381(16) 0.0192(3) Uani 1 1 d . . . H3 H 0.5105(19) 0.8854(13) 0.278(2) 0.026(5) Uiso 1 1 d . . . C1 C 0.72055(16) 0.84960(10) 0.53851(18) 0.0183(4) Uani 1 1 d . . . C2 C 0.66768(16) 0.76133(11) 0.56407(18) 0.0191(4) Uani 1 1 d . . . C3 C 0.48788(16) 0.78587(11) 0.38915(18) 0.0188(4) Uani 1 1 d . . . C4 C 0.65971(16) 0.89200(10) 0.40512(18) 0.0178(4) Uani 1 1 d . . . C5 C 0.68245(17) 0.90453(11) 0.66602(19) 0.0226(4) Uani 1 1 d . . . H5A H 0.7249 0.8808 0.7536 0.027 Uiso 1 1 calc R . . H5B H 0.7174 0.9619 0.6537 0.027 Uiso 1 1 calc R . . C6 C 0.53822(17) 0.91180(12) 0.6872(2) 0.0260(4) Uani 1 1 d . . . H6A H 0.4959 0.9408 0.6057 0.039 Uiso 1 1 calc R . . H6B H 0.5249 0.9440 0.7736 0.039 Uiso 1 1 calc R . . H6C H 0.5012 0.8553 0.6958 0.039 Uiso 1 1 calc R . . C7 C 0.86690(17) 0.84384(11) 0.52693(18) 0.0204(4) Uani 1 1 d . . . C8 C 0.95294(18) 0.89314(13) 0.6081(2) 0.0327(5) Uani 1 1 d . . . H8 H 0.9212 0.9322 0.6738 0.039 Uiso 1 1 calc R . . C9 C 1.0856(2) 0.88590(15) 0.5941(3) 0.0417(6) Uani 1 1 d . . . H9 H 1.1436 0.9202 0.6500 0.050 Uiso 1 1 calc R . . C10 C 1.13237(19) 0.82947(14) 0.5000(2) 0.0375(5) Uani 1 1 d . . . H10 H 1.2228 0.8241 0.4917 0.045 Uiso 1 1 calc R . . C11 C 1.04815(19) 0.78041(14) 0.4174(2) 0.0331(5) Uani 1 1 d . . . H11 H 1.0804 0.7417 0.3513 0.040 Uiso 1 1 calc R . . C12 C 0.91624(18) 0.78776(12) 0.4310(2) 0.0264(4) Uani 1 1 d . . . H12 H 0.8587 0.7539 0.3738 0.032 Uiso 1 1 calc R . . C13 C 0.22434(17) 0.89085(12) 0.1225(2) 0.0296(5) Uani 1 1 d . . . H13 H 0.2436 0.8437 0.1818 0.036 Uiso 1 1 calc R . . C14 C 0.09917(17) 0.91719(12) 0.1002(2) 0.0294(5) Uani 1 1 d . . . H14 H 0.0327 0.8885 0.1459 0.035 Uiso 1 1 calc R . . C15 C 0.06723(15) 0.98515(10) 0.01182(18) 0.0178(4) Uani 1 1 d . . . C16 C 0.16924(16) 1.02440(12) -0.05121(19) 0.0249(4) Uani 1 1 d . . . H16 H 0.1524 1.0709 -0.1127 0.030 Uiso 1 1 calc R . . C17 C 0.29388(17) 0.99708(12) -0.02620(19) 0.0243(4) Uani 1 1 d . . . H17 H 0.3621 1.0247 -0.0706 0.029 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0123(6) 0.0237(7) 0.0246(7) -0.0008(5) -0.0011(5) 0.0044(5) O2 0.0272(7) 0.0255(7) 0.0262(7) 0.0078(5) -0.0045(6) -0.0020(5) O3 0.0185(6) 0.0268(7) 0.0300(7) 0.0015(6) -0.0039(5) -0.0030(5) O4 0.0242(7) 0.0202(7) 0.0267(7) 0.0041(5) 0.0013(5) -0.0021(5) N1 0.0135(7) 0.0183(7) 0.0191(7) -0.0030(6) -0.0006(6) 0.0019(5) N2 0.0201(8) 0.0158(8) 0.0227(8) 0.0015(6) 0.0006(6) -0.0026(6) N3 0.0191(7) 0.0199(8) 0.0185(8) 0.0028(6) 0.0004(6) 0.0010(6) C1 0.0186(9) 0.0188(9) 0.0175(8) -0.0009(7) 0.0009(7) -0.0006(7) C2 0.0200(9) 0.0213(9) 0.0162(8) -0.0009(7) 0.0029(7) 0.0004(7) C3 0.0188(8) 0.0192(9) 0.0187(9) -0.0031(7) 0.0025(7) 0.0021(7) C4 0.0183(8) 0.0160(9) 0.0197(9) -0.0022(7) 0.0045(7) 0.0024(7) C5 0.0257(9) 0.0229(9) 0.0192(9) -0.0031(7) 0.0000(7) -0.0004(7) C6 0.0291(10) 0.0248(10) 0.0245(10) -0.0041(8) 0.0051(8) 0.0050(8) C7 0.0215(9) 0.0197(9) 0.0201(9) 0.0051(7) 0.0007(7) 0.0003(7) C8 0.0243(10) 0.0326(11) 0.0414(12) -0.0096(9) 0.0025(9) -0.0054(8) C9 0.0240(11) 0.0448(13) 0.0562(15) -0.0068(11) 0.0013(10) -0.0124(9) C10 0.0210(10) 0.0485(13) 0.0434(12) 0.0096(11) 0.0059(9) 0.0017(9) C11 0.0296(11) 0.0414(12) 0.0290(11) 0.0011(9) 0.0064(8) 0.0102(9) C12 0.0258(10) 0.0306(10) 0.0226(10) -0.0003(8) -0.0013(8) 0.0038(8) C13 0.0204(9) 0.0248(10) 0.0434(12) 0.0149(9) 0.0002(8) 0.0000(7) C14 0.0154(9) 0.0282(10) 0.0447(12) 0.0137(9) 0.0035(8) -0.0003(7) C15 0.0170(9) 0.0191(8) 0.0171(8) -0.0028(7) -0.0008(6) -0.0006(7) C16 0.0205(9) 0.0316(11) 0.0226(9) 0.0106(8) 0.0017(7) 0.0029(8) C17 0.0194(9) 0.0306(10) 0.0229(9) 0.0077(8) 0.0033(7) -0.0007(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 O1 N1 1.3277(17) . ? O2 C2 1.211(2) . ? O3 C3 1.213(2) . ? O4 C4 1.207(2) . ? N1 C17 1.344(2) . ? N1 C13 1.347(2) . ? N2 C2 1.372(2) . ? N2 C3 1.377(2) . ? N2 H2 0.94(2) . ? N3 C3 1.371(2) . ? N3 C4 1.373(2) . ? N3 H3 0.87(2) . ? C1 C2 1.529(2) . ? C1 C7 1.531(2) . ? C1 C4 1.534(2) . ? C1 C5 1.556(2) . ? C5 C6 1.525(2) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 C8 1.386(3) . ? C7 C12 1.388(3) . ? C8 C9 1.395(3) . ? C8 H8 0.9500 . ? C9 C10 1.370(3) . ? C9 H9 0.9500 . ? C10 C11 1.380(3) . ? C10 H10 0.9500 . ? C11 C12 1.387(3) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C14 1.370(2) . ? C13 H13 0.9500 . ? C14 C15 1.393(2) . ? C14 H14 0.9500 . ? C15 C16 1.390(2) . ? C15 C15 1.478(3) 3_575 ? C16 C17 1.372(2) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? 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 N1 C17 119.14(14) . . ? O1 N1 C13 120.49(14) . . ? C17 N1 C13 120.36(15) . . ? C2 N2 C3 126.51(15) . . ? C2 N2 H2 117.3(12) . . ? C3 N2 H2 116.1(12) . . ? C3 N3 C4 126.57(15) . . ? C3 N3 H3 116.3(13) . . ? C4 N3 H3 115.2(13) . . ? C2 C1 C7 108.81(13) . . ? C2 C1 C4 113.39(14) . . ? C7 C1 C4 109.40(14) . . ? C2 C1 C5 106.41(14) . . ? C7 C1 C5 112.59(13) . . ? C4 C1 C5 106.27(13) . . ? O2 C2 N2 120.61(16) . . ? O2 C2 C1 121.78(15) . . ? N2 C2 C1 117.53(14) . . ? O3 C3 N3 122.55(16) . . ? O3 C3 N2 121.22(16) . . ? N3 C3 N2 116.22(15) . . ? O4 C4 N3 121.22(15) . . ? O4 C4 C1 121.91(15) . . ? N3 C4 C1 116.69(15) . . ? C6 C5 C1 115.91(14) . . ? C6 C5 H5A 108.3 . . ? C1 C5 H5A 108.3 . . ? C6 C5 H5B 108.3 . . ? C1 C5 H5B 108.3 . . ? H5A C5 H5B 107.4 . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C8 C7 C12 118.28(17) . . ? C8 C7 C1 122.52(16) . . ? C12 C7 C1 119.20(15) . . ? C7 C8 C9 120.7(2) . . ? C7 C8 H8 119.7 . . ? C9 C8 H8 119.7 . . ? C10 C9 C8 120.1(2) . . ? C10 C9 H9 119.9 . . ? C8 C9 H9 119.9 . . ? C9 C10 C11 120.02(19) . . ? C9 C10 H10 120.0 . . ? C11 C10 H10 120.0 . . ? C10 C11 C12 119.8(2) . . ? C10 C11 H11 120.1 . . ? C12 C11 H11 120.1 . . ? C11 C12 C7 121.07(18) . . ? C11 C12 H12 119.5 . . ? C7 C12 H12 119.5 . . ? N1 C13 C14 120.28(17) . . ? N1 C13 H13 119.9 . . ? C14 C13 H13 119.9 . . ? C13 C14 C15 121.39(17) . . ? C13 C14 H14 119.3 . . ? C15 C14 H14 119.3 . . ? C16 C15 C14 116.26(16) . . ? C16 C15 C15 121.79(19) . 3_575 ? C14 C15 C15 121.9(2) . 3_575 ? C17 C16 C15 121.14(17) . . ? C17 C16 H16 119.4 . . ? C15 C16 H16 119.4 . . ? N1 C17 C16 120.56(16) . . ? N1 C17 H17 119.7 . . ? C16 C17 H17 119.7 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.04 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.326 _refine_diff_density_min -0.228 _refine_diff_density_rms 0.053 # Attachment 'Piclin Noxide 3.cif' data_pbca_2 _database_code_depnum_ccdc_archive 'CCDC 288483' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Pyridine-2-carboxamide-N-oxide ; _chemical_name_common Pyridine-2-carboxamide-N-oxide _chemical_melting_point ? _chemical_formula_moiety 'C6 H6 N2 O2' _chemical_formula_sum 'C6 H6 N2 O2' _chemical_formula_weight 138.13 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 Orthorhombic _symmetry_space_group_name_H-M 'P b c a ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 12.940(3) _cell_length_b 7.3496(19) _cell_length_c 13.087(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1244.6(6) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1325 _cell_measurement_theta_min 3.11 _cell_measurement_theta_max 25.91 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.474 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 576 _exptl_absorpt_coefficient_mu 0.114 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9453 _exptl_absorpt_correction_T_max 0.9943 _exptl_absorpt_process_details 'Bruker AXS SADABS program' _exptl_special_details ; Sheldrick,G.M.,(2003),University of gottingen,Germany ; _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 3790 _diffrn_reflns_av_R_equivalents 0.0253 _diffrn_reflns_av_sigmaI/netI 0.0247 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 3.11 _diffrn_reflns_theta_max 26.04 _reflns_number_total 1219 _reflns_number_gt 905 _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 ? _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^)+(0.0723P)^2^+0.2372P] 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 1219 _refine_ls_number_parameters 99 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0692 _refine_ls_R_factor_gt 0.0504 _refine_ls_wR_factor_ref 0.1405 _refine_ls_wR_factor_gt 0.1280 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _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 O1 O 0.66047(10) 0.0112(2) 0.53101(10) 0.0505(5) Uani 1 1 d . . . O2 O 0.93897(9) 0.1481(2) 0.40292(11) 0.0551(5) Uani 1 1 d . . . N1 N 0.66609(11) 0.0915(2) 0.44170(12) 0.0380(4) Uani 1 1 d . . . N2 N 0.86090(15) 0.0121(3) 0.53560(14) 0.0491(5) Uani 1 1 d . . . H2B H 0.794(2) -0.020(3) 0.5584(19) 0.077(8) Uiso 1 1 d . . . H2A H 0.9173(18) -0.031(3) 0.5579(17) 0.057(7) Uiso 1 1 d . . . C1 C 0.75791(13) 0.1415(2) 0.39904(14) 0.0352(5) Uani 1 1 d . . . C2 C 0.75688(15) 0.2249(3) 0.30481(15) 0.0427(5) Uani 1 1 d . . . H2 H 0.8193 0.2597 0.2754 0.051 Uiso 1 1 calc R . . C3 C 0.66675(16) 0.2583(3) 0.25309(16) 0.0505(6) Uani 1 1 d . . . H3 H 0.6672 0.3151 0.1896 0.061 Uiso 1 1 calc R . . C4 C 0.57611(16) 0.2055(3) 0.29792(17) 0.0548(6) Uani 1 1 d . . . H4 H 0.5138 0.2258 0.2645 0.066 Uiso 1 1 calc R . . C5 C 0.57649(15) 0.1234(3) 0.39118(17) 0.0510(6) Uani 1 1 d . . . H5 H 0.5142 0.0885 0.4207 0.061 Uiso 1 1 calc R . . C6 C 0.86057(14) 0.1008(3) 0.44815(15) 0.0395(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 O1 0.0406(8) 0.0746(11) 0.0362(8) 0.0108(7) 0.0035(6) -0.0052(7) O2 0.0346(8) 0.0751(11) 0.0556(10) 0.0153(8) 0.0057(6) 0.0002(7) N1 0.0349(9) 0.0467(10) 0.0325(9) -0.0036(7) -0.0009(7) -0.0004(6) N2 0.0340(9) 0.0660(12) 0.0474(11) 0.0148(9) -0.0053(8) 0.0047(9) C1 0.0340(10) 0.0358(10) 0.0357(10) -0.0046(8) 0.0014(8) 0.0011(7) C2 0.0446(11) 0.0434(11) 0.0401(11) 0.0000(9) 0.0049(9) -0.0001(8) C3 0.0641(13) 0.0522(12) 0.0353(11) 0.0033(10) -0.0066(10) 0.0033(10) C4 0.0436(12) 0.0699(16) 0.0509(14) -0.0008(11) -0.0164(10) 0.0029(10) C5 0.0346(10) 0.0685(15) 0.0498(13) -0.0020(11) -0.0040(9) -0.0026(9) C6 0.0331(10) 0.0442(11) 0.0413(11) -0.0016(9) 0.0019(8) 0.0025(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 N1 1.311(2) . ? O2 C6 1.225(2) . ? N1 C5 1.355(2) . ? N1 C1 1.363(2) . ? N2 C6 1.317(3) . ? N2 H2B 0.94(3) . ? N2 H2A 0.85(2) . ? C1 C2 1.377(3) . ? C1 C6 1.506(2) . ? C2 C3 1.371(3) . ? C2 H2 0.9300 . ? C3 C4 1.368(3) . ? C3 H3 0.9300 . ? C4 C5 1.362(3) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? 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 N1 C5 117.72(15) . . ? O1 N1 C1 122.32(14) . . ? C5 N1 C1 119.96(18) . . ? C6 N2 H2B 113.3(16) . . ? C6 N2 H2A 119.1(15) . . ? H2B N2 H2A 126(2) . . ? N1 C1 C2 118.57(16) . . ? N1 C1 C6 122.72(17) . . ? C2 C1 C6 118.63(16) . . ? C3 C2 C1 122.01(18) . . ? C3 C2 H2 119.0 . . ? C1 C2 H2 119.0 . . ? C4 C3 C2 117.8(2) . . ? C4 C3 H3 121.1 . . ? C2 C3 H3 121.1 . . ? C5 C4 C3 120.49(18) . . ? C5 C4 H4 119.8 . . ? C3 C4 H4 119.8 . . ? N1 C5 C4 121.13(19) . . ? N1 C5 H5 119.4 . . ? C4 C5 H5 119.4 . . ? O2 C6 N2 123.91(18) . . ? O2 C6 C1 117.90(18) . . ? N2 C6 C1 118.16(17) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.04 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.193 _refine_diff_density_min -0.221 _refine_diff_density_rms 0.059 # Attachment 'Pyrazin Noxide 4.cif' data_an239_m _database_code_depnum_ccdc_archive 'CCDC 288484' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Pyrazinamide-4-N-oxide ; _chemical_name_common Pyrazinamide-4-N-oxide _chemical_melting_point ? _chemical_formula_moiety 'C5 H5 N3 O2' _chemical_formula_sum 'C5 H5 N3 O2' _chemical_formula_weight 139.12 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 5.403(3) _cell_length_b 7.508(4) _cell_length_c 14.978(8) _cell_angle_alpha 96.838(9) _cell_angle_beta 97.094(9) _cell_angle_gamma 102.822(9) _cell_volume 581.2(6) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2979 _cell_measurement_theta_min 2.77 _cell_measurement_theta_max 26.13 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.590 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 288 _exptl_absorpt_coefficient_mu 0.127 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9545 _exptl_absorpt_correction_T_max 0.9874 _exptl_absorpt_process_details 'Bruker AXS SADABS program' _exptl_special_details ; Sheldrick,G.M.,(2003),University of gottingen,Germany ; _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 5890 _diffrn_reflns_av_R_equivalents 0.0467 _diffrn_reflns_av_sigmaI/netI 0.0560 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.39 _diffrn_reflns_theta_max 26.19 _reflns_number_total 2323 _reflns_number_gt 1829 _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 ? _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^)+(0.1170P)^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_extinction_coef ? _refine_ls_number_reflns 2323 _refine_ls_number_parameters 197 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0815 _refine_ls_R_factor_gt 0.0669 _refine_ls_wR_factor_ref 0.1933 _refine_ls_wR_factor_gt 0.1811 _refine_ls_goodness_of_fit_ref 1.089 _refine_ls_restrained_S_all 1.089 _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 N5 N 0.3282(3) 0.1326(3) 0.23775(12) 0.0349(5) Uani 1 1 d . . . N3 N 0.3259(3) 0.6583(2) 0.26445(12) 0.0334(5) Uani 1 1 d . . . O1 O -0.2413(3) 0.5305(2) 0.41798(11) 0.0464(5) Uani 1 1 d . . . O3 O -0.1245(3) 0.0772(3) 0.39159(12) 0.0521(5) Uani 1 1 d . . . O2 O -0.1174(3) 0.2991(2) 0.11017(11) 0.0454(5) Uani 1 1 d . . . C1 C -0.0887(4) 0.4862(3) 0.28312(15) 0.0337(5) Uani 1 1 d . . . H1 H -0.2380 0.3975 0.2576 0.040 Uiso 1 1 calc R . . C3 C 0.3464(4) 0.7420(3) 0.35077(15) 0.0369(5) Uani 1 1 d . . . H3 H 0.4964 0.8309 0.3753 0.044 Uiso 1 1 calc R . . N1 N -0.0613(3) 0.5732(2) 0.37012(12) 0.0339(5) Uani 1 1 d . . . C6 C -0.0926(4) -0.0671(3) 0.21672(16) 0.0339(5) Uani 1 1 d . . . H6 H -0.2410 -0.1098 0.2411 0.041 Uiso 1 1 calc R . . C8 C 0.3414(4) 0.0634(3) 0.15147(16) 0.0385(6) Uani 1 1 d . . . H8 H 0.4901 0.1083 0.1277 0.046 Uiso 1 1 calc R . . N6 N 0.2807(4) 0.2530(3) 0.41230(16) 0.0470(6) Uani 1 1 d . . . C2 C 0.1074(4) 0.5316(3) 0.23359(15) 0.0321(5) Uani 1 1 d . . . C7 C 0.1091(4) 0.0633(3) 0.26760(15) 0.0333(5) Uani 1 1 d . . . N4 N -0.0733(3) -0.1333(2) 0.13014(13) 0.0366(5) Uani 1 1 d . . . N2 N 0.2563(4) 0.4845(3) 0.08931(16) 0.0461(6) Uani 1 1 d . . . C4 C 0.1597(4) 0.7038(3) 0.40456(15) 0.0360(5) Uani 1 1 d . . . H4 H 0.1831 0.7661 0.4636 0.043 Uiso 1 1 calc R . . C9 C 0.1494(4) -0.0686(3) 0.09710(16) 0.0364(6) Uani 1 1 d . . . H9 H 0.1696 -0.1139 0.0386 0.044 Uiso 1 1 calc R . . C5 C 0.0732(4) 0.4280(3) 0.13763(15) 0.0340(5) Uani 1 1 d . . . C10 C 0.0806(4) 0.1330(3) 0.36453(16) 0.0351(5) Uani 1 1 d . . . O4 O -0.2622(3) -0.2538(3) 0.08148(12) 0.0569(6) Uani 1 1 d . . . H6B H 0.411(7) 0.278(4) 0.378(2) 0.080(10) Uiso 1 1 d . . . H2B H 0.388(7) 0.565(5) 0.119(2) 0.080(11) Uiso 1 1 d . . . H6A H 0.272(5) 0.300(4) 0.4614(19) 0.043(7) Uiso 1 1 d . . . H2A H 0.248(5) 0.424(4) 0.033(2) 0.062(8) 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 N5 0.0289(9) 0.0348(10) 0.0361(11) 0.0006(8) 0.0059(8) -0.0006(8) N3 0.0285(9) 0.0335(10) 0.0320(10) 0.0009(8) 0.0042(7) -0.0032(8) O1 0.0388(9) 0.0535(11) 0.0375(10) -0.0071(8) 0.0161(8) -0.0068(8) O3 0.0396(9) 0.0597(11) 0.0418(11) -0.0110(9) 0.0094(8) -0.0119(8) O2 0.0413(9) 0.0468(10) 0.0386(10) -0.0035(8) 0.0128(7) -0.0076(8) C1 0.0313(11) 0.0309(12) 0.0311(12) -0.0051(9) 0.0017(9) -0.0021(9) C3 0.0322(11) 0.0342(12) 0.0359(13) -0.0017(10) 0.0023(9) -0.0045(9) N1 0.0333(9) 0.0314(10) 0.0327(10) -0.0004(8) 0.0047(8) 0.0019(8) C6 0.0314(11) 0.0337(12) 0.0322(12) -0.0010(9) 0.0080(9) 0.0003(9) C8 0.0317(11) 0.0435(14) 0.0382(13) 0.0049(10) 0.0112(9) 0.0019(10) N6 0.0395(12) 0.0576(14) 0.0318(12) -0.0119(10) 0.0092(10) -0.0059(10) C2 0.0308(11) 0.0277(11) 0.0343(12) 0.0021(9) 0.0036(9) 0.0019(9) C7 0.0289(10) 0.0333(12) 0.0365(13) 0.0050(10) 0.0062(9) 0.0044(9) N4 0.0361(10) 0.0344(11) 0.0348(11) -0.0014(8) 0.0095(8) 0.0005(8) N2 0.0437(12) 0.0488(13) 0.0328(12) -0.0095(10) 0.0123(10) -0.0115(10) C4 0.0401(12) 0.0354(12) 0.0294(12) 0.0002(10) 0.0066(10) 0.0045(10) C9 0.0383(12) 0.0354(13) 0.0308(12) -0.0036(10) 0.0069(10) 0.0028(10) C5 0.0332(11) 0.0303(12) 0.0338(12) -0.0007(10) 0.0044(9) 0.0013(9) C10 0.0319(11) 0.0350(12) 0.0348(12) 0.0011(10) 0.0076(10) 0.0015(9) O4 0.0432(10) 0.0625(12) 0.0422(11) -0.0227(9) 0.0121(8) -0.0218(9) _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 N5 C7 1.336(3) . ? N5 C8 1.351(3) . ? N3 C2 1.332(3) . ? N3 C3 1.349(3) . ? O1 N1 1.285(2) . ? O3 C10 1.230(3) . ? O2 C5 1.235(3) . ? C1 N1 1.361(3) . ? C1 C2 1.373(3) . ? C1 H1 0.9300 . ? C3 C4 1.370(3) . ? C3 H3 0.9300 . ? N1 C4 1.364(3) . ? C6 N4 1.357(3) . ? C6 C7 1.368(3) . ? C6 H6 0.9300 . ? C8 C9 1.366(3) . ? C8 H8 0.9300 . ? N6 C10 1.310(3) . ? N6 H6B 0.92(4) . ? N6 H6A 0.79(3) . ? C2 C5 1.519(3) . ? C7 C10 1.522(3) . ? N4 O4 1.281(2) . ? N4 C9 1.369(3) . ? N2 C5 1.321(3) . ? N2 H2B 0.86(4) . ? N2 H2A 0.90(3) . ? C4 H4 0.9300 . ? C9 H9 0.9300 . ? 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 C7 N5 C8 115.10(19) . . ? C2 N3 C3 115.11(17) . . ? N1 C1 C2 118.9(2) . . ? N1 C1 H1 120.5 . . ? C2 C1 H1 120.5 . . ? N3 C3 C4 123.9(2) . . ? N3 C3 H3 118.0 . . ? C4 C3 H3 118.0 . . ? O1 N1 C1 119.83(18) . . ? O1 N1 C4 121.52(19) . . ? C1 N1 C4 118.65(18) . . ? N4 C6 C7 119.1(2) . . ? N4 C6 H6 120.5 . . ? C7 C6 H6 120.5 . . ? N5 C8 C9 123.87(19) . . ? N5 C8 H8 118.1 . . ? C9 C8 H8 118.1 . . ? C10 N6 H6B 111(2) . . ? C10 N6 H6A 119.9(19) . . ? H6B N6 H6A 129(3) . . ? N3 C2 C1 124.4(2) . . ? N3 C2 C5 118.11(18) . . ? C1 C2 C5 117.5(2) . . ? N5 C7 C6 124.3(2) . . ? N5 C7 C10 118.2(2) . . ? C6 C7 C10 117.47(19) . . ? O4 N4 C6 119.63(18) . . ? O4 N4 C9 121.66(19) . . ? C6 N4 C9 118.71(19) . . ? C5 N2 H2B 115(2) . . ? C5 N2 H2A 119.2(19) . . ? H2B N2 H2A 125(3) . . ? N1 C4 C3 119.0(2) . . ? N1 C4 H4 120.5 . . ? C3 C4 H4 120.5 . . ? C8 C9 N4 118.9(2) . . ? C8 C9 H9 120.5 . . ? N4 C9 H9 120.5 . . ? O2 C5 N2 124.6(2) . . ? O2 C5 C2 119.39(19) . . ? N2 C5 C2 116.0(2) . . ? O3 C10 N6 125.1(2) . . ? O3 C10 C7 119.0(2) . . ? N6 C10 C7 115.8(2) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 26.19 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.478 _refine_diff_density_min -0.339 _refine_diff_density_rms 0.083