# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2005 data_global _journal_coden_Cambridge 177 loop_ _publ_author_name 'Jean Bernadou' 'Vania Bernardes-Genisson' 'Sylvain Broussy' 'Heinz Gornitzka' 'Bernard Meunier' _publ_contact_author_name 'Prof Jean Bernadou' _publ_contact_author_address ; Lab Chim Coord CNRS CNRS 205 route de Narbonne Toulouse France 31077 Toulouse Cedex 4 ; _publ_contact_author_email BERNADOU@LCC-TOULOUSE.FR _publ_requested_journal 'Organic & Biomolecular Chemistry' _publ_section_title ; Studies on the 4-benzoylpyridine-3-carboxamide entity as a fragment model of the isoniazid-NAD adduct ; data_16 _database_code_depnum_ccdc_archive 'CCDC 252382' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H10 N2 O2' _chemical_formula_weight 226.23 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)/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 10.245(2) _cell_length_b 7.1600(13) _cell_length_c 15.020(3) _cell_angle_alpha 90.00 _cell_angle_beta 107.943(4) _cell_angle_gamma 90.00 _cell_volume 1048.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 2159 _cell_measurement_theta_min 2.851 _cell_measurement_theta_max 26.347 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.05 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.434 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 472 _exptl_absorpt_coefficient_mu 0.099 _exptl_absorpt_correction_type semi-empirical _exptl_absorpt_correction_T_min 0.698893 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_process_details 'SADABS (Bruker-AXS)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 193(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker CCD 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 5860 _diffrn_reflns_av_R_equivalents 0.0343 _diffrn_reflns_av_sigmaI/netI 0.0401 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 26.44 _reflns_number_total 2147 _reflns_number_gt 1646 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0348P)^2^+0.3882P] 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 2147 _refine_ls_number_parameters 159 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0593 _refine_ls_R_factor_gt 0.0411 _refine_ls_wR_factor_ref 0.0962 _refine_ls_wR_factor_gt 0.0887 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.44327(14) 0.2620(2) 0.18668(10) 0.0287(3) Uani 1 1 d . . . H1A H 0.454(2) 0.231(3) 0.2458(15) 0.042(6) Uiso 1 1 d . . . N2 N 0.40975(15) 0.3142(2) -0.12521(9) 0.0291(3) Uani 1 1 d . . . O1 O 0.29943(13) 0.53378(17) 0.15324(8) 0.0310(3) Uani 1 1 d . . . H1 H 0.3119 0.5442 0.2110 0.046 Uiso 1 1 calc R . . O2 O 0.64017(12) 0.13626(17) 0.16610(8) 0.0334(3) Uani 1 1 d . . . C1 C 0.31265(17) 0.3453(2) 0.13117(11) 0.0252(4) Uani 1 1 d . . . C2 C 0.52740(17) 0.2122(2) 0.13673(11) 0.0256(4) Uani 1 1 d . . . C3 C 0.45451(17) 0.2663(2) 0.03803(11) 0.0237(4) Uani 1 1 d . . . C4 C 0.32979(16) 0.3431(2) 0.03402(10) 0.0232(4) Uani 1 1 d . . . C5 C 0.24374(17) 0.4091(2) -0.04955(11) 0.0280(4) Uani 1 1 d . . . H5 H 0.1577 0.4647 -0.0540 0.034 Uiso 1 1 calc R . . C6 C 0.28973(18) 0.3900(2) -0.12701(11) 0.0288(4) Uani 1 1 d . . . H6 H 0.2316 0.4340 -0.1855 0.035 Uiso 1 1 calc R . . C7 C 0.49259(18) 0.2536(2) -0.04252(11) 0.0272(4) Uani 1 1 d . . . H7 H 0.5791 0.2009 -0.0392 0.033 Uiso 1 1 calc R . . C8 C 0.19178(16) 0.2261(2) 0.13570(10) 0.0251(4) Uani 1 1 d . . . C9 C 0.07878(17) 0.3047(3) 0.15310(12) 0.0318(4) Uani 1 1 d . . . H9 H 0.0767 0.4353 0.1636 0.038 Uiso 1 1 calc R . . C10 C -0.03177(19) 0.1942(3) 0.15531(13) 0.0385(5) Uani 1 1 d . . . H10 H -0.1081 0.2495 0.1685 0.046 Uiso 1 1 calc R . . C11 C -0.0313(2) 0.0053(3) 0.13859(13) 0.0385(5) Uani 1 1 d . . . H11 H -0.1078 -0.0694 0.1388 0.046 Uiso 1 1 calc R . . C12 C 0.0817(2) -0.0752(3) 0.12147(13) 0.0416(5) Uani 1 1 d . . . H12 H 0.0831 -0.2057 0.1106 0.050 Uiso 1 1 calc R . . C13 C 0.1921(2) 0.0338(3) 0.12022(12) 0.0352(4) Uani 1 1 d . . . H13 H 0.2692 -0.0226 0.1087 0.042 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0275(7) 0.0420(9) 0.0175(7) 0.0028(6) 0.0085(6) 0.0003(7) N2 0.0384(8) 0.0308(8) 0.0207(7) -0.0027(6) 0.0128(6) -0.0068(7) O1 0.0383(7) 0.0331(7) 0.0246(6) -0.0069(5) 0.0142(5) -0.0047(6) O2 0.0277(6) 0.0416(7) 0.0310(6) 0.0072(6) 0.0090(5) 0.0060(6) C1 0.0259(8) 0.0311(9) 0.0198(8) -0.0012(7) 0.0089(7) 0.0003(7) C2 0.0276(9) 0.0263(9) 0.0236(8) 0.0012(7) 0.0090(7) -0.0044(7) C3 0.0270(8) 0.0222(8) 0.0229(8) -0.0018(6) 0.0089(7) -0.0035(7) C4 0.0274(8) 0.0230(8) 0.0203(8) -0.0019(6) 0.0087(7) -0.0050(7) C5 0.0278(9) 0.0322(9) 0.0236(8) 0.0002(7) 0.0073(7) -0.0015(7) C6 0.0339(9) 0.0307(9) 0.0195(8) 0.0006(7) 0.0047(7) -0.0061(8) C7 0.0313(9) 0.0268(9) 0.0266(8) -0.0028(7) 0.0136(7) -0.0016(7) C8 0.0271(8) 0.0329(9) 0.0153(7) 0.0007(7) 0.0066(6) -0.0006(7) C9 0.0304(9) 0.0304(9) 0.0367(10) 0.0029(8) 0.0132(8) 0.0026(8) C10 0.0289(9) 0.0452(12) 0.0447(11) 0.0059(9) 0.0162(9) 0.0019(9) C11 0.0386(11) 0.0430(11) 0.0360(10) 0.0019(8) 0.0147(8) -0.0129(9) C12 0.0561(13) 0.0314(10) 0.0428(11) -0.0052(8) 0.0230(10) -0.0088(9) C13 0.0405(11) 0.0365(10) 0.0342(10) -0.0044(8) 0.0199(8) 0.0004(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 N1 C2 1.353(2) . ? N1 C1 1.468(2) . ? N2 C6 1.337(2) . ? N2 C7 1.342(2) . ? O1 C1 1.406(2) . ? O2 C2 1.229(2) . ? C1 C8 1.522(2) . ? C1 C4 1.523(2) . ? C2 C3 1.491(2) . ? C3 C4 1.375(2) . ? C3 C7 1.384(2) . ? C4 C5 1.376(2) . ? C5 C6 1.390(2) . ? C8 C9 1.382(2) . ? C8 C13 1.396(3) . ? C9 C10 1.390(3) . ? C10 C11 1.376(3) . ? C11 C12 1.387(3) . ? C12 C13 1.378(3) . ? 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 C2 N1 C1 114.65(13) . . ? C6 N2 C7 117.74(14) . . ? O1 C1 N1 113.16(13) . . ? O1 C1 C8 112.87(13) . . ? N1 C1 C8 111.03(13) . . ? O1 C1 C4 106.46(13) . . ? N1 C1 C4 100.73(13) . . ? C8 C1 C4 111.88(13) . . ? O2 C2 N1 127.31(15) . . ? O2 C2 C3 126.81(15) . . ? N1 C2 C3 105.87(14) . . ? C4 C3 C7 119.75(15) . . ? C4 C3 C2 108.75(14) . . ? C7 C3 C2 131.49(16) . . ? C3 C4 C5 120.19(15) . . ? C3 C4 C1 109.99(13) . . ? C5 C4 C1 129.79(15) . . ? C4 C5 C6 116.26(16) . . ? N2 C6 C5 124.75(15) . . ? N2 C7 C3 121.30(16) . . ? C9 C8 C13 118.51(16) . . ? C9 C8 C1 121.37(15) . . ? C13 C8 C1 120.11(15) . . ? C8 C9 C10 120.59(17) . . ? C11 C10 C9 120.41(18) . . ? C10 C11 C12 119.51(18) . . ? C13 C12 C11 120.15(18) . . ? C12 C13 C8 120.82(17) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.44 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.271 _refine_diff_density_min -0.183 _refine_diff_density_rms 0.039 #===END