Electronic Supplementary Material for CrystEngComm This Journal is © The Royal SOciety of Chemistry 2004 data_global _publ_contact_author_email AAKEROY@KSU.EDU _publ_contact_author_name 'Dr Christer Aakeroy' _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_address ; Department of Chemistry Kansas State University Willard Hall Manhattan Kansas 66506 UNITED STATES OF AMERICA ; _publ_section_title ; Well, this is a bit weird! A binary cocrystal with little discernible benefit to the two participants. ; loop_ _publ_author_name 'Christer Aakeroy' 'John Desper' 'Brian A. Helfrich' data_1 _database_code_depnum_ccdc_archive 'CCDC 224989' _chemical_name_common ;2-(4-(dimethylamino)phenylazo)benzoic acid, 3,5- dinitrobenzoic acid ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2-[4-(dimethylamino)phenylazo]benzoic acid, 3,5-dinitrobenzoic acid ; _chemical_melting_point '148-150 (dec)' _chemical_formula_moiety ; (C15 H15 N3 O2) (C7 H4 N2 O6) ; _chemical_formula_sum 'C22 H19 N5 O8' _chemical_formula_weight 481.42 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 7.0051(5) _cell_length_b 8.6187(7) _cell_length_c 18.5866(15) _cell_angle_alpha 101.186(2) _cell_angle_beta 97.114(2) _cell_angle_gamma 101.401(2) _cell_volume 1063.66(14) _cell_formula_units_Z 2 _cell_measurement_temperature 203(2) _cell_measurement_reflns_used 2368 _cell_measurement_theta_min 2.50 _cell_measurement_theta_max 27.2 _exptl_crystal_description plate _exptl_crystal_colour red _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.503 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 500 _exptl_absorpt_coefficient_mu 0.117 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 203(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 8137 _diffrn_reflns_av_R_equivalents 0.0508 _diffrn_reflns_av_sigmaI/netI 0.0669 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.27 _diffrn_reflns_theta_max 28.21 _reflns_number_total 4765 _reflns_number_gt 2692 _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^)+(0.0700P)^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 0.064(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4765 _refine_ls_number_parameters 323 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0835 _refine_ls_R_factor_gt 0.0471 _refine_ls_wR_factor_ref 0.1278 _refine_ls_wR_factor_gt 0.1117 _refine_ls_goodness_of_fit_ref 0.891 _refine_ls_restrained_S_all 0.891 _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 C1 C 0.2478(2) 0.3052(2) 0.61067(9) 0.0328(4) Uani 1 1 d . . . C2 C 0.3005(3) 0.3538(2) 0.68838(10) 0.0354(4) Uani 1 1 d . . . C3 C 0.2852(3) 0.2340(2) 0.72942(10) 0.0403(5) Uani 1 1 d . . . H3 H 0.3199 0.2647 0.7815 0.048 Uiso 1 1 calc R . . C4 C 0.2208(3) 0.0723(3) 0.69554(11) 0.0433(5) Uani 1 1 d . . . H4 H 0.2117 -0.0067 0.7242 0.052 Uiso 1 1 calc R . . C5 C 0.1692(3) 0.0262(2) 0.61860(11) 0.0408(5) Uani 1 1 d . . . H5 H 0.1242 -0.0843 0.5951 0.049 Uiso 1 1 calc R . . C6 C 0.1836(3) 0.1410(2) 0.57680(10) 0.0359(4) Uani 1 1 d . . . H6 H 0.1498 0.1086 0.5247 0.043 Uiso 1 1 calc R . . O7 O 0.4225(2) 0.56045(18) 0.79677(8) 0.0620(4) Uani 1 1 d . . . C7 C 0.3734(3) 0.5257(3) 0.72907(11) 0.0440(5) Uani 1 1 d . . . O8 O 0.3850(2) 0.64019(17) 0.69175(8) 0.0541(4) Uani 1 1 d . . . H8 H 0.344(3) 0.582(3) 0.6375(13) 0.065 Uiso 1 1 d . . . N9 N 0.2639(2) 0.42995(18) 0.57033(8) 0.0325(3) Uani 1 1 d . . . N10 N 0.2174(2) 0.38124(18) 0.49998(8) 0.0355(4) Uani 1 1 d . . . C11 C 0.2315(3) 0.5005(2) 0.45928(10) 0.0337(4) Uani 1 1 d . . . C12 C 0.1799(3) 0.4452(2) 0.38238(10) 0.0381(4) Uani 1 1 d . . . H12 H 0.1386 0.3329 0.3620 0.046 Uiso 1 1 calc R . . C13 C 0.1879(3) 0.5502(2) 0.33601(10) 0.0401(5) Uani 1 1 d . . . H13 H 0.1527 0.5090 0.2843 0.048 Uiso 1 1 calc R . . C14 C 0.2479(2) 0.7191(2) 0.36414(10) 0.0341(4) Uani 1 1 d . . . C15 C 0.2991(3) 0.7747(2) 0.44252(10) 0.0386(4) Uani 1 1 d . . . H15 H 0.3391 0.8868 0.4634 0.046 Uiso 1 1 calc R . . C16 C 0.2913(3) 0.6677(2) 0.48821(10) 0.0365(4) Uani 1 1 d . . . H16 H 0.3269 0.7075 0.5400 0.044 Uiso 1 1 calc R . . N17 N 0.2558(2) 0.82228(19) 0.31752(9) 0.0408(4) Uani 1 1 d . . . C18 C 0.2041(3) 0.7603(3) 0.23747(11) 0.0502(5) Uani 1 1 d . . . H18A H 0.2873 0.6873 0.2213 0.075 Uiso 1 1 calc R . . H18B H 0.2239 0.8502 0.2128 0.075 Uiso 1 1 calc R . . H18C H 0.0667 0.7022 0.2249 0.075 Uiso 1 1 calc R . . C19 C 0.3171(3) 0.9977(2) 0.34458(13) 0.0546(6) Uani 1 1 d . . . H19A H 0.2282 1.0343 0.3767 0.082 Uiso 1 1 calc R . . H19B H 0.3135 1.0496 0.3027 0.082 Uiso 1 1 calc R . . H19C H 0.4505 1.0262 0.3724 0.082 Uiso 1 1 calc R . . C21 C 0.6894(3) 1.0914(2) 0.95849(9) 0.0336(4) Uani 1 1 d . . . C22 C 0.6803(3) 1.2506(2) 0.96045(10) 0.0379(4) Uani 1 1 d . . . H22 H 0.6137 1.2785 0.9194 0.045 Uiso 1 1 calc R . . N23 N 0.7626(3) 1.5386(2) 1.02524(12) 0.0560(5) Uani 1 1 d . . . C23 C 0.7701(3) 1.3682(2) 1.02340(11) 0.0393(5) Uani 1 1 d . . . O23 O 0.6839(3) 1.5685(2) 0.96900(11) 0.0821(6) Uani 1 1 d . . . O24 O 0.8353(3) 1.63903(19) 1.08151(11) 0.0872(6) Uani 1 1 d . . . C24 C 0.8664(3) 1.3332(2) 1.08520(10) 0.0381(4) Uani 1 1 d . . . H24 H 0.9256 1.4147 1.1279 0.046 Uiso 1 1 calc R . . O25 O 1.0259(2) 1.23669(18) 1.20393(8) 0.0656(5) Uani 1 1 d . . . N25 N 0.9685(2) 1.1311(2) 1.14751(9) 0.0420(4) Uani 1 1 d . . . C25 C 0.8722(3) 1.1737(2) 1.08165(10) 0.0336(4) Uani 1 1 d . . . O26 O 0.9858(2) 0.99167(17) 1.14194(7) 0.0502(4) Uani 1 1 d . . . C26 C 0.7876(2) 1.0520(2) 1.01960(9) 0.0323(4) Uani 1 1 d . . . H26 H 0.7962 0.9442 1.0186 0.039 Uiso 1 1 calc R . . O27 O 0.4774(2) 0.99457(17) 0.84181(7) 0.0521(4) Uani 1 1 d . . . C27 C 0.5846(3) 0.9650(2) 0.89078(10) 0.0378(4) Uani 1 1 d . . . O28 O 0.6192(2) 0.82275(17) 0.89296(7) 0.0475(4) Uani 1 1 d . . . H28 H 0.566(3) 0.752(3) 0.8570(12) 0.057 Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0278(9) 0.0376(11) 0.0322(10) 0.0075(8) 0.0026(7) 0.0072(8) C2 0.0305(9) 0.0420(11) 0.0314(10) 0.0058(8) 0.0022(7) 0.0072(8) C3 0.0380(11) 0.0520(13) 0.0313(10) 0.0118(9) 0.0048(8) 0.0095(9) C4 0.0422(11) 0.0479(13) 0.0436(12) 0.0200(10) 0.0068(9) 0.0095(9) C5 0.0419(11) 0.0355(11) 0.0443(12) 0.0106(9) 0.0052(9) 0.0068(9) C6 0.0363(10) 0.0379(11) 0.0305(10) 0.0065(8) 0.0005(8) 0.0060(8) O7 0.0818(11) 0.0564(10) 0.0324(8) -0.0005(7) -0.0029(7) -0.0021(8) C7 0.0435(11) 0.0450(12) 0.0366(11) 0.0024(9) 0.0030(9) 0.0030(9) O8 0.0742(10) 0.0398(9) 0.0379(8) 0.0001(7) 0.0016(7) 0.0022(7) N9 0.0334(8) 0.0337(9) 0.0286(8) 0.0049(7) 0.0024(6) 0.0070(7) N10 0.0381(9) 0.0350(9) 0.0311(8) 0.0063(7) 0.0026(6) 0.0062(7) C11 0.0355(10) 0.0321(10) 0.0329(10) 0.0067(8) 0.0039(8) 0.0080(8) C12 0.0470(11) 0.0292(10) 0.0346(10) 0.0038(8) 0.0025(8) 0.0067(8) C13 0.0491(12) 0.0372(11) 0.0327(10) 0.0076(8) 0.0041(8) 0.0085(9) C14 0.0289(9) 0.0375(11) 0.0393(10) 0.0133(8) 0.0075(8) 0.0095(8) C15 0.0404(11) 0.0296(10) 0.0417(11) 0.0035(9) 0.0033(8) 0.0050(8) C16 0.0394(10) 0.0348(11) 0.0318(10) 0.0030(8) 0.0025(8) 0.0069(8) N17 0.0452(9) 0.0365(9) 0.0442(10) 0.0174(8) 0.0079(7) 0.0090(7) C18 0.0569(13) 0.0576(14) 0.0427(12) 0.0247(10) 0.0083(10) 0.0152(11) C19 0.0563(13) 0.0382(12) 0.0727(15) 0.0211(11) 0.0140(11) 0.0087(10) C21 0.0362(10) 0.0354(10) 0.0308(9) 0.0112(8) 0.0076(8) 0.0070(8) C22 0.0404(11) 0.0412(12) 0.0365(10) 0.0181(9) 0.0077(8) 0.0099(9) N23 0.0645(13) 0.0360(11) 0.0749(14) 0.0236(11) 0.0157(11) 0.0153(10) C23 0.0440(11) 0.0286(10) 0.0499(12) 0.0147(9) 0.0128(9) 0.0105(8) O23 0.1089(15) 0.0541(11) 0.0957(14) 0.0436(10) 0.0045(11) 0.0294(10) O24 0.1268(17) 0.0282(9) 0.0932(14) 0.0014(9) -0.0053(12) 0.0129(10) C24 0.0436(11) 0.0310(10) 0.0371(10) 0.0043(8) 0.0070(8) 0.0055(8) O25 0.0956(13) 0.0498(10) 0.0382(8) -0.0038(7) -0.0161(8) 0.0163(9) N25 0.0495(10) 0.0376(10) 0.0348(9) 0.0059(8) -0.0012(7) 0.0074(8) C25 0.0369(10) 0.0316(10) 0.0320(10) 0.0081(8) 0.0032(8) 0.0073(8) O26 0.0658(10) 0.0375(8) 0.0466(8) 0.0132(7) -0.0041(7) 0.0149(7) C26 0.0360(10) 0.0284(10) 0.0348(10) 0.0096(8) 0.0082(8) 0.0086(8) O27 0.0594(9) 0.0568(10) 0.0369(8) 0.0151(7) -0.0053(7) 0.0096(7) C27 0.0429(11) 0.0400(11) 0.0320(10) 0.0140(9) 0.0082(8) 0.0058(9) O28 0.0643(10) 0.0338(8) 0.0359(8) 0.0027(6) -0.0051(7) 0.0049(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 C6 1.391(2) . ? C1 C2 1.404(2) . ? C1 N9 1.420(2) . ? C2 C3 1.393(3) . ? C2 C7 1.483(3) . ? C3 C4 1.372(3) . ? C3 H3 0.9400 . ? C4 C5 1.389(3) . ? C4 H4 0.9400 . ? C5 C6 1.368(3) . ? C5 H5 0.9400 . ? C6 H6 0.9400 . ? O7 C7 1.224(2) . ? C7 O8 1.307(2) . ? O8 H8 1.01(2) . ? N9 N10 1.2726(19) . ? N10 C11 1.385(2) . ? C11 C12 1.393(2) . ? C11 C16 1.396(2) . ? C12 C13 1.364(3) . ? C12 H12 0.9400 . ? C13 C14 1.406(3) . ? C13 H13 0.9400 . ? C14 N17 1.355(2) . ? C14 C15 1.419(2) . ? C15 C16 1.367(3) . ? C15 H15 0.9400 . ? C16 H16 0.9400 . ? N17 C18 1.453(2) . ? N17 C19 1.455(2) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C18 H18C 0.9700 . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C19 H19C 0.9700 . ? C21 C22 1.380(2) . ? C21 C26 1.388(2) . ? C21 C27 1.494(3) . ? C22 C23 1.377(3) . ? C22 H22 0.9400 . ? N23 O24 1.202(2) . ? N23 O23 1.217(2) . ? N23 C23 1.474(2) . ? C23 C24 1.374(3) . ? C24 C25 1.372(2) . ? C24 H24 0.9400 . ? O25 N25 1.2125(19) . ? N25 O26 1.2172(19) . ? N25 C25 1.468(2) . ? C25 C26 1.377(2) . ? C26 H26 0.9400 . ? O27 C27 1.206(2) . ? C27 O28 1.303(2) . ? O28 H28 0.81(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 C6 C1 C2 119.80(17) . . ? C6 C1 N9 123.18(16) . . ? C2 C1 N9 117.02(16) . . ? C3 C2 C1 118.26(17) . . ? C3 C2 C7 118.26(17) . . ? C1 C2 C7 123.47(17) . . ? C4 C3 C2 121.52(18) . . ? C4 C3 H3 119.2 . . ? C2 C3 H3 119.2 . . ? C3 C4 C5 119.51(18) . . ? C3 C4 H4 120.2 . . ? C5 C4 H4 120.2 . . ? C6 C5 C4 120.30(19) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? C5 C6 C1 120.59(17) . . ? C5 C6 H6 119.7 . . ? C1 C6 H6 119.7 . . ? O7 C7 O8 120.22(19) . . ? O7 C7 C2 120.55(19) . . ? O8 C7 C2 119.23(17) . . ? C7 O8 H8 105.5(13) . . ? N10 N9 C1 115.24(15) . . ? N9 N10 C11 116.44(15) . . ? N10 C11 C12 115.73(16) . . ? N10 C11 C16 126.13(16) . . ? C12 C11 C16 118.14(17) . . ? C13 C12 C11 121.52(18) . . ? C13 C12 H12 119.2 . . ? C11 C12 H12 119.2 . . ? C12 C13 C14 121.14(18) . . ? C12 C13 H13 119.4 . . ? C14 C13 H13 119.4 . . ? N17 C14 C13 120.63(17) . . ? N17 C14 C15 122.28(17) . . ? C13 C14 C15 117.09(17) . . ? C16 C15 C14 121.03(18) . . ? C16 C15 H15 119.5 . . ? C14 C15 H15 119.5 . . ? C15 C16 C11 121.08(17) . . ? C15 C16 H16 119.5 . . ? C11 C16 H16 119.5 . . ? C14 N17 C18 120.60(16) . . ? C14 N17 C19 122.19(17) . . ? C18 N17 C19 117.21(16) . . ? N17 C18 H18A 109.5 . . ? N17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? N17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N17 C19 H19A 109.5 . . ? N17 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? N17 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C22 C21 C26 119.85(17) . . ? C22 C21 C27 118.16(17) . . ? C26 C21 C27 121.94(17) . . ? C23 C22 C21 119.05(18) . . ? C23 C22 H22 120.5 . . ? C21 C22 H22 120.5 . . ? O24 N23 O23 124.2(2) . . ? O24 N23 C23 118.4(2) . . ? O23 N23 C23 117.4(2) . . ? C24 C23 C22 122.61(18) . . ? C24 C23 N23 118.28(19) . . ? C22 C23 N23 119.11(19) . . ? C25 C24 C23 116.94(18) . . ? C25 C24 H24 121.5 . . ? C23 C24 H24 121.5 . . ? O25 N25 O26 124.11(17) . . ? O25 N25 C25 118.10(17) . . ? O26 N25 C25 117.79(16) . . ? C24 C25 C26 122.70(17) . . ? C24 C25 N25 118.40(17) . . ? C26 C25 N25 118.89(16) . . ? C25 C26 C21 118.84(17) . . ? C25 C26 H26 120.6 . . ? C21 C26 H26 120.6 . . ? O27 C27 O28 125.55(19) . . ? O27 C27 C21 122.34(18) . . ? O28 C27 C21 112.08(17) . . ? C27 O28 H28 114.9(16) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -0.4(2) . . . . ? N9 C1 C2 C3 179.70(15) . . . . ? C6 C1 C2 C7 179.01(16) . . . . ? N9 C1 C2 C7 -0.9(2) . . . . ? C1 C2 C3 C4 0.1(3) . . . . ? C7 C2 C3 C4 -179.36(16) . . . . ? C2 C3 C4 C5 -0.1(3) . . . . ? C3 C4 C5 C6 0.4(3) . . . . ? C4 C5 C6 C1 -0.7(3) . . . . ? C2 C1 C6 C5 0.7(3) . . . . ? N9 C1 C6 C5 -179.37(16) . . . . ? C3 C2 C7 O7 1.5(3) . . . . ? C1 C2 C7 O7 -177.89(18) . . . . ? C3 C2 C7 O8 -178.63(18) . . . . ? C1 C2 C7 O8 2.0(3) . . . . ? C6 C1 N9 N10 -0.8(2) . . . . ? C2 C1 N9 N10 179.08(14) . . . . ? C1 N9 N10 C11 179.88(14) . . . . ? N9 N10 C11 C12 -179.93(15) . . . . ? N9 N10 C11 C16 0.0(3) . . . . ? N10 C11 C12 C13 -179.80(17) . . . . ? C16 C11 C12 C13 0.3(3) . . . . ? C11 C12 C13 C14 -0.3(3) . . . . ? C12 C13 C14 N17 179.81(18) . . . . ? C12 C13 C14 C15 -0.1(3) . . . . ? N17 C14 C15 C16 -179.45(17) . . . . ? C13 C14 C15 C16 0.5(3) . . . . ? C14 C15 C16 C11 -0.4(3) . . . . ? N10 C11 C16 C15 -179.83(17) . . . . ? C12 C11 C16 C15 0.1(3) . . . . ? C13 C14 N17 C18 -0.6(3) . . . . ? C15 C14 N17 C18 179.35(17) . . . . ? C13 C14 N17 C19 179.96(16) . . . . ? C15 C14 N17 C19 -0.1(3) . . . . ? C26 C21 C22 C23 0.2(3) . . . . ? C27 C21 C22 C23 177.78(15) . . . . ? C21 C22 C23 C24 -1.1(3) . . . . ? C21 C22 C23 N23 179.28(16) . . . . ? O24 N23 C23 C24 -2.4(3) . . . . ? O23 N23 C23 C24 177.04(19) . . . . ? O24 N23 C23 C22 177.29(19) . . . . ? O23 N23 C23 C22 -3.3(3) . . . . ? C22 C23 C24 C25 0.8(3) . . . . ? N23 C23 C24 C25 -179.56(16) . . . . ? C23 C24 C25 C26 0.3(3) . . . . ? C23 C24 C25 N25 -178.13(16) . . . . ? O25 N25 C25 C24 5.3(3) . . . . ? O26 N25 C25 C24 -174.65(16) . . . . ? O25 N25 C25 C26 -173.21(16) . . . . ? O26 N25 C25 C26 6.8(3) . . . . ? C24 C25 C26 C21 -1.1(3) . . . . ? N25 C25 C26 C21 177.33(15) . . . . ? C22 C21 C26 C25 0.8(2) . . . . ? C27 C21 C26 C25 -176.63(15) . . . . ? C22 C21 C27 O27 -7.6(3) . . . . ? C26 C21 C27 O27 169.89(17) . . . . ? C22 C21 C27 O28 174.18(16) . . . . ? C26 C21 C27 O28 -8.3(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O28 H28 O7 0.81(2) 1.82(2) 2.6069(19) 163(2) . O8 H8 N9 1.01(2) 1.58(2) 2.5353(19) 156(2) . C13 H13 O25 0.94 2.45 3.184(2) 134.6 1_444 _diffrn_measured_fraction_theta_max 0.907 _diffrn_reflns_theta_full 28.21 _diffrn_measured_fraction_theta_full 0.907 _refine_diff_density_max 0.271 _refine_diff_density_min -0.215 _refine_diff_density_rms 0.064 data_2 _database_code_depnum_ccdc_archive 'CCDC 224990' _chemical_name_common '3-nitrobenzoic acid, isonicotinamide' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3-nitrobenzoic acid, isonicotinamide ; _chemical_melting_point 160-162 _chemical_formula_moiety ; (C7 H5 N O4) (C6 H6 N2 O) ; _chemical_formula_sum 'C13 H11 N3 O5' _chemical_formula_weight 289.25 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 5.9827(4) _cell_length_b 9.1713(8) _cell_length_c 12.1893(8) _cell_angle_alpha 84.149(5) _cell_angle_beta 77.407(6) _cell_angle_gamma 74.927(5) _cell_volume 629.54(8) _cell_formula_units_Z 2 _cell_measurement_temperature 203(2) _cell_measurement_reflns_used 1290 _cell_measurement_theta_min 2.30 _cell_measurement_theta_max 26.90 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.526 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 300 _exptl_absorpt_coefficient_mu 0.120 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 203(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 4649 _diffrn_reflns_av_R_equivalents 0.0467 _diffrn_reflns_av_sigmaI/netI 0.1158 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.71 _diffrn_reflns_theta_max 28.27 _reflns_number_total 2786 _reflns_number_gt 1306 _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^)+(0.0450P)^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 0.039(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2786 _refine_ls_number_parameters 200 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1089 _refine_ls_R_factor_gt 0.0464 _refine_ls_wR_factor_ref 0.1036 _refine_ls_wR_factor_gt 0.0910 _refine_ls_goodness_of_fit_ref 0.787 _refine_ls_restrained_S_all 0.787 _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 N11 N 0.8592(3) 0.59112(19) 0.80660(14) 0.0321(5) Uani 1 1 d . . . C12 C 1.0926(4) 0.5508(2) 0.77232(18) 0.0349(6) Uani 1 1 d . . . H12 H 1.1655 0.6128 0.7176 0.042 Uiso 1 1 calc R . . C13 C 1.2313(4) 0.4221(2) 0.81358(18) 0.0308(6) Uani 1 1 d . . . H13 H 1.3957 0.3972 0.7872 0.037 Uiso 1 1 calc R . . C14 C 1.1282(3) 0.3298(2) 0.89378(17) 0.0264(5) Uani 1 1 d . . . C15 C 0.8849(3) 0.3702(2) 0.92828(17) 0.0303(6) Uani 1 1 d . . . H15 H 0.8069 0.3094 0.9818 0.036 Uiso 1 1 calc R . . C16 C 0.7609(4) 0.5002(2) 0.88299(18) 0.0345(6) Uani 1 1 d . . . H16 H 0.5959 0.5271 0.9073 0.041 Uiso 1 1 calc R . . C17 C 1.2851(4) 0.1917(2) 0.93797(17) 0.0291(5) Uani 1 1 d . . . N17 N 1.1903(3) 0.1080(2) 1.02015(16) 0.0372(5) Uani 1 1 d . . . H17A H 1.297(4) 0.016(3) 1.0478(17) 0.045 Uiso 1 1 d . . . H17B H 1.046(4) 0.129(2) 1.0514(18) 0.045 Uiso 1 1 d . . . O17 O 1.4974(2) 0.15758(17) 0.89518(13) 0.0410(4) Uani 1 1 d . . . C21 C 0.2980(3) 1.0247(2) 0.69626(17) 0.0275(5) Uani 1 1 d . . . C22 C 0.4325(3) 1.1001(2) 0.61468(16) 0.0279(5) Uani 1 1 d . . . H22 H 0.5977 1.0648 0.5965 0.033 Uiso 1 1 calc R . . C23 C 0.3191(4) 1.2278(2) 0.56080(17) 0.0285(5) Uani 1 1 d . . . C24 C 0.0777(4) 1.2825(2) 0.58342(18) 0.0348(6) Uani 1 1 d . . . H24 H 0.0048 1.3698 0.5449 0.042 Uiso 1 1 calc R . . C25 C -0.0536(4) 1.2061(3) 0.66374(18) 0.0367(6) Uani 1 1 d . . . H25 H -0.2189 1.2414 0.6811 0.044 Uiso 1 1 calc R . . C26 C 0.0549(3) 1.0784(2) 0.71898(18) 0.0341(6) Uani 1 1 d . . . H26 H -0.0375 1.0265 0.7733 0.041 Uiso 1 1 calc R . . C27 C 0.4115(4) 0.8868(2) 0.75727(17) 0.0299(6) Uani 1 1 d . . . O27 O 0.6385(3) 0.83941(18) 0.71715(13) 0.0384(4) Uani 1 1 d . . . H27 H 0.722(4) 0.732(3) 0.7580(17) 0.046 Uiso 1 1 d . . . O28 O 0.3046(2) 0.82331(16) 0.83563(12) 0.0405(5) Uani 1 1 d . . . N28 N 0.4617(3) 1.3090(2) 0.47545(15) 0.0358(5) Uani 1 1 d . . . O29 O 0.6744(3) 1.25240(18) 0.45101(12) 0.0436(5) Uani 1 1 d . . . O30 O 0.3639(3) 1.42766(18) 0.43232(14) 0.0508(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 N11 0.0298(10) 0.0276(12) 0.0328(11) 0.0050(9) -0.0033(8) -0.0013(9) C12 0.0330(13) 0.0351(15) 0.0326(13) 0.0069(11) -0.0011(10) -0.0092(11) C13 0.0263(11) 0.0268(14) 0.0348(13) 0.0040(11) -0.0009(10) -0.0054(10) C14 0.0276(11) 0.0258(13) 0.0239(12) 0.0000(10) -0.0044(9) -0.0040(10) C15 0.0234(11) 0.0297(14) 0.0312(13) 0.0081(11) 0.0006(9) -0.0036(10) C16 0.0264(12) 0.0356(15) 0.0345(14) 0.0024(11) 0.0008(10) -0.0024(11) C17 0.0239(11) 0.0288(13) 0.0309(13) 0.0017(11) -0.0015(10) -0.0043(10) N17 0.0251(10) 0.0327(13) 0.0418(13) 0.0118(10) 0.0017(9) 0.0016(9) O17 0.0255(8) 0.0417(11) 0.0454(10) 0.0129(8) -0.0018(7) 0.0003(7) C21 0.0288(11) 0.0271(13) 0.0242(12) -0.0017(10) -0.0028(9) -0.0043(10) C22 0.0284(12) 0.0236(13) 0.0270(13) 0.0000(10) -0.0045(10) 0.0004(10) C23 0.0302(12) 0.0265(13) 0.0261(12) 0.0017(10) -0.0040(9) -0.0049(10) C24 0.0360(13) 0.0283(14) 0.0360(14) 0.0046(11) -0.0108(11) -0.0001(11) C25 0.0249(12) 0.0399(16) 0.0415(15) -0.0005(12) -0.0065(10) -0.0016(11) C26 0.0291(12) 0.0377(15) 0.0319(13) 0.0015(12) 0.0012(10) -0.0092(11) C27 0.0264(12) 0.0280(14) 0.0308(13) 0.0018(11) -0.0022(10) -0.0029(10) O27 0.0287(8) 0.0328(10) 0.0417(9) 0.0122(8) 0.0004(7) 0.0019(7) O28 0.0352(9) 0.0374(10) 0.0385(10) 0.0116(8) 0.0044(7) -0.0054(8) N28 0.0390(12) 0.0299(13) 0.0351(12) 0.0036(10) -0.0074(9) -0.0047(10) O29 0.0341(9) 0.0459(11) 0.0427(10) 0.0112(8) 0.0003(8) -0.0074(8) O30 0.0518(10) 0.0322(11) 0.0602(12) 0.0205(9) -0.0119(9) -0.0038(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 N11 C16 1.329(2) . ? N11 C12 1.330(2) . ? N11 H27 1.48(2) . ? C12 C13 1.373(3) . ? C12 H12 0.9400 . ? C13 C14 1.376(3) . ? C13 H13 0.9400 . ? C14 C15 1.385(3) . ? C14 C17 1.495(3) . ? C15 C16 1.364(3) . ? C15 H15 0.9400 . ? C16 H16 0.9400 . ? C17 O17 1.234(2) . ? C17 N17 1.318(2) . ? N17 H17A 0.99(2) . ? N17 H17B 0.84(2) . ? C21 C22 1.384(3) . ? C21 C26 1.384(3) . ? C21 C27 1.482(3) . ? C22 C23 1.374(3) . ? C22 H22 0.9400 . ? C23 C24 1.375(3) . ? C23 N28 1.467(2) . ? C24 C25 1.370(3) . ? C24 H24 0.9400 . ? C25 C26 1.371(3) . ? C25 H25 0.9400 . ? C26 H26 0.9400 . ? C27 O28 1.214(2) . ? C27 O27 1.311(2) . ? O27 H27 1.11(2) . ? N28 O30 1.220(2) . ? N28 O29 1.225(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 C16 N11 C12 117.29(18) . . ? C16 N11 H27 123.4(8) . . ? C12 N11 H27 119.3(8) . . ? N11 C12 C13 122.65(19) . . ? N11 C12 H12 118.7 . . ? C13 C12 H12 118.7 . . ? C12 C13 C14 119.64(19) . . ? C12 C13 H13 120.2 . . ? C14 C13 H13 120.2 . . ? C13 C14 C15 117.82(19) . . ? C13 C14 C17 118.18(18) . . ? C15 C14 C17 124.00(18) . . ? C16 C15 C14 118.63(19) . . ? C16 C15 H15 120.7 . . ? C14 C15 H15 120.7 . . ? N11 C16 C15 123.94(19) . . ? N11 C16 H16 118.0 . . ? C15 C16 H16 118.0 . . ? O17 C17 N17 121.9(2) . . ? O17 C17 C14 119.40(18) . . ? N17 C17 C14 118.69(18) . . ? C17 N17 H17A 117.4(12) . . ? C17 N17 H17B 124.2(15) . . ? H17A N17 H17B 118.4(19) . . ? C22 C21 C26 119.0(2) . . ? C22 C21 C27 120.71(18) . . ? C26 C21 C27 120.24(19) . . ? C23 C22 C21 118.50(19) . . ? C23 C22 H22 120.8 . . ? C21 C22 H22 120.8 . . ? C22 C23 C24 122.81(19) . . ? C22 C23 N28 118.55(18) . . ? C24 C23 N28 118.64(19) . . ? C25 C24 C23 118.1(2) . . ? C25 C24 H24 120.9 . . ? C23 C24 H24 120.9 . . ? C24 C25 C26 120.33(19) . . ? C24 C25 H25 119.8 . . ? C26 C25 H25 119.8 . . ? C25 C26 C21 121.18(19) . . ? C25 C26 H26 119.4 . . ? C21 C26 H26 119.4 . . ? O28 C27 O27 123.49(19) . . ? O28 C27 C21 123.42(19) . . ? O27 C27 C21 113.09(17) . . ? C27 O27 H27 113.7(10) . . ? O30 N28 O29 123.58(18) . . ? O30 N28 C23 118.95(18) . . ? O29 N28 C23 117.47(18) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C16 N11 C12 C13 -0.8(3) . . . . ? N11 C12 C13 C14 -0.1(4) . . . . ? C12 C13 C14 C15 1.1(3) . . . . ? C12 C13 C14 C17 -179.2(2) . . . . ? C13 C14 C15 C16 -1.2(3) . . . . ? C17 C14 C15 C16 179.1(2) . . . . ? C12 N11 C16 C15 0.6(3) . . . . ? C14 C15 C16 N11 0.4(4) . . . . ? C13 C14 C17 O17 -6.1(3) . . . . ? C15 C14 C17 O17 173.6(2) . . . . ? C13 C14 C17 N17 175.5(2) . . . . ? C15 C14 C17 N17 -4.8(3) . . . . ? C26 C21 C22 C23 1.3(3) . . . . ? C27 C21 C22 C23 -179.8(2) . . . . ? C21 C22 C23 C24 -0.9(3) . . . . ? C21 C22 C23 N28 179.13(19) . . . . ? C22 C23 C24 C25 0.4(4) . . . . ? N28 C23 C24 C25 -179.66(19) . . . . ? C23 C24 C25 C26 -0.3(3) . . . . ? C24 C25 C26 C21 0.7(4) . . . . ? C22 C21 C26 C25 -1.3(3) . . . . ? C27 C21 C26 C25 179.8(2) . . . . ? C22 C21 C27 O28 173.8(2) . . . . ? C26 C21 C27 O28 -7.3(4) . . . . ? C22 C21 C27 O27 -6.9(3) . . . . ? C26 C21 C27 O27 172.04(19) . . . . ? C22 C23 N28 O30 -175.4(2) . . . . ? C24 C23 N28 O30 4.6(3) . . . . ? C22 C23 N28 O29 5.0(3) . . . . ? C24 C23 N28 O29 -174.9(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O27 H27 N11 1.11(2) 1.48(2) 2.584(2) 173.9(18) . N17 H17A O17 0.99(2) 1.91(2) 2.907(2) 178.4(19) 2_857 N17 H17B O28 0.84(2) 2.21(2) 3.040(2) 169(2) 2_667 C12 H12 O29 0.94 2.43 3.356(3) 168.0 2_776 C24 H24 O30 0.94 2.47 3.248(3) 140.1 2_586 _diffrn_measured_fraction_theta_max 0.893 _diffrn_reflns_theta_full 28.27 _diffrn_measured_fraction_theta_full 0.893 _refine_diff_density_max 0.250 _refine_diff_density_min -0.200 _refine_diff_density_rms 0.049 data_3 _database_code_depnum_ccdc_archive 'CCDC 224991' _chemical_name_common 'isonicotinamide, 4-fluorobenzoic acid' _audit_creation_method SHELXL-97 _chemical_name_systematic ; isonicotinamide, 4-fluorobenzoic acid ; _chemical_melting_point 153-155 _chemical_formula_moiety ; (C6 H6 N2 O) (C7 H5 F O2) ; _chemical_formula_sum 'C13 H11 F N2 O3' _chemical_formula_weight 262.24 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c 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' '-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 22.725(13) _cell_length_b 5.231(3) _cell_length_c 20.785(12) _cell_angle_alpha 90.00 _cell_angle_beta 95.402(11) _cell_angle_gamma 90.00 _cell_volume 2460(2) _cell_formula_units_Z 8 _cell_measurement_temperature 203(2) _cell_measurement_reflns_used 617 _cell_measurement_theta_min 2.75 _cell_measurement_theta_max 23.45 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.416 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1088 _exptl_absorpt_coefficient_mu 0.112 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 203(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 P4' _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 8008 _diffrn_reflns_av_R_equivalents 0.1491 _diffrn_reflns_av_sigmaI/netI 0.1586 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 26.55 _reflns_number_total 2520 _reflns_number_gt 1070 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _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^)+(0.0700P)^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 0.0119(13) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2520 _refine_ls_number_parameters 182 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1392 _refine_ls_R_factor_gt 0.0604 _refine_ls_wR_factor_ref 0.1624 _refine_ls_wR_factor_gt 0.1269 _refine_ls_goodness_of_fit_ref 0.868 _refine_ls_restrained_S_all 0.868 _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 0.39043(11) 0.4010(4) 0.32302(11) 0.0490(6) Uani 1 1 d . . . C2 C 0.43565(13) 0.2686(5) 0.30379(14) 0.0541(8) Uani 1 1 d . . . H2 H 0.4495 0.3117 0.2640 0.065 Uiso 1 1 calc R . . C3 C 0.46327(14) 0.0722(5) 0.33891(12) 0.0527(8) Uani 1 1 d . . . H3 H 0.4948 -0.0169 0.3230 0.063 Uiso 1 1 calc R . . C4 C 0.44405(11) 0.0079(4) 0.39776(11) 0.0399(7) Uani 1 1 d . . . C5 C 0.39709(13) 0.1444(5) 0.41818(13) 0.0494(8) Uani 1 1 d . . . H5 H 0.3825 0.1061 0.4579 0.059 Uiso 1 1 calc R . . C6 C 0.37183(13) 0.3375(6) 0.37959(13) 0.0542(8) Uani 1 1 d . . . H6 H 0.3399 0.4285 0.3940 0.065 Uiso 1 1 calc R . . O7 O 0.44724(9) -0.2485(3) 0.49165(9) 0.0564(6) Uani 1 1 d . . . N7 N 0.51467(11) -0.3353(4) 0.42204(11) 0.0474(7) Uani 1 1 d . . . H71 H 0.5275(12) -0.467(5) 0.4479(12) 0.057 Uiso 1 1 d . . . H72 H 0.5332(13) -0.298(5) 0.3849(13) 0.057 Uiso 1 1 d . . . C7 C 0.46949(12) -0.2029(5) 0.44093(13) 0.0411(7) Uani 1 1 d . . . C11 C 0.33613(12) 1.0376(5) 0.16165(12) 0.0434(7) Uani 1 1 d . . . C12 C 0.35880(14) 1.1224(6) 0.10610(13) 0.0572(8) Uani 1 1 d . . . H12 H 0.3939 1.0505 0.0936 0.069 Uiso 1 1 calc R . . C13 C 0.33044(15) 1.3116(6) 0.06879(15) 0.0688(10) Uani 1 1 d . . . H13 H 0.3455 1.3691 0.0307 0.083 Uiso 1 1 calc R . . F14 F 0.25160(9) 1.5990(4) 0.05223(9) 0.0960(8) Uani 1 1 d . . . C14 C 0.28012(15) 1.4122(6) 0.08868(14) 0.0591(9) Uani 1 1 d . . . C15 C 0.25622(14) 1.3355(6) 0.14330(14) 0.0616(9) Uani 1 1 d . . . H15 H 0.2213 1.4097 0.1555 0.074 Uiso 1 1 calc R . . C16 C 0.28503(13) 1.1454(5) 0.18005(14) 0.0518(8) Uani 1 1 d . . . H16 H 0.2696 1.0891 0.2180 0.062 Uiso 1 1 calc R . . O17 O 0.34021(9) 0.7646(4) 0.25167(9) 0.0575(6) Uani 1 1 d . . . H17 H 0.3626(13) 0.619(5) 0.2778(13) 0.069 Uiso 1 1 d . . . C17 C 0.36761(13) 0.8342(5) 0.20143(13) 0.0443(7) Uani 1 1 d . . . O18 O 0.41438(9) 0.7391(3) 0.18904(9) 0.0573(6) 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 N1 0.0504(16) 0.0545(14) 0.0422(14) 0.0059(12) 0.0043(12) 0.0021(12) C2 0.059(2) 0.0672(19) 0.0379(16) 0.0125(15) 0.0150(15) 0.0077(16) C3 0.056(2) 0.0611(18) 0.0431(17) 0.0100(15) 0.0153(15) 0.0098(15) C4 0.0414(17) 0.0452(15) 0.0331(15) 0.0018(12) 0.0042(13) -0.0020(12) C5 0.054(2) 0.0574(17) 0.0387(16) 0.0085(14) 0.0112(14) 0.0032(14) C6 0.052(2) 0.0608(18) 0.0507(19) 0.0062(15) 0.0089(16) 0.0099(14) O7 0.0649(15) 0.0639(13) 0.0433(12) 0.0135(10) 0.0210(11) 0.0104(10) N7 0.0506(16) 0.0526(15) 0.0402(14) 0.0102(12) 0.0105(12) 0.0065(12) C7 0.0424(18) 0.0454(16) 0.0358(15) 0.0019(13) 0.0063(13) -0.0019(13) C11 0.0426(18) 0.0548(17) 0.0333(15) 0.0044(13) 0.0069(13) 0.0000(13) C12 0.055(2) 0.074(2) 0.0446(18) 0.0061(17) 0.0157(16) 0.0061(16) C13 0.071(3) 0.086(3) 0.053(2) 0.0223(18) 0.0230(18) 0.0052(19) F14 0.0966(18) 0.1110(17) 0.0814(14) 0.0504(13) 0.0139(12) 0.0329(13) C14 0.059(2) 0.067(2) 0.0505(19) 0.0194(17) 0.0009(17) 0.0062(16) C15 0.055(2) 0.079(2) 0.0524(19) 0.0111(17) 0.0142(16) 0.0154(17) C16 0.053(2) 0.0626(18) 0.0414(16) 0.0091(15) 0.0127(14) 0.0058(15) O17 0.0513(14) 0.0761(14) 0.0476(12) 0.0240(11) 0.0177(10) 0.0150(10) C17 0.0415(18) 0.0561(17) 0.0361(16) -0.0002(14) 0.0083(14) -0.0025(14) O18 0.0496(14) 0.0721(13) 0.0522(13) 0.0053(11) 0.0157(10) 0.0098(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C6 1.328(3) . ? N1 C2 1.332(3) . ? C2 C3 1.377(4) . ? C2 H2 0.9400 . ? C3 C4 1.379(3) . ? C3 H3 0.9400 . ? C4 C5 1.384(4) . ? C4 C7 1.502(3) . ? C5 C6 1.381(4) . ? C5 H5 0.9400 . ? C6 H6 0.9400 . ? O7 C7 1.235(3) . ? N7 C7 1.328(3) . ? N7 H71 0.91(2) . ? N7 H72 0.93(3) . ? C11 C16 1.377(4) . ? C11 C12 1.381(4) . ? C11 C17 1.489(4) . ? C12 C13 1.379(4) . ? C12 H12 0.9400 . ? C13 C14 1.358(4) . ? C13 H13 0.9400 . ? F14 C14 1.362(3) . ? C14 C15 1.364(4) . ? C15 C16 1.381(4) . ? C15 H15 0.9400 . ? C16 H16 0.9400 . ? O17 C17 1.317(3) . ? O17 H17 1.04(3) . ? C17 O18 1.223(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 C6 N1 C2 117.0(2) . . ? N1 C2 C3 123.7(3) . . ? N1 C2 H2 118.1 . . ? C3 C2 H2 118.1 . . ? C2 C3 C4 119.0(3) . . ? C2 C3 H3 120.5 . . ? C4 C3 H3 120.5 . . ? C3 C4 C5 117.7(3) . . ? C3 C4 C7 124.9(2) . . ? C5 C4 C7 117.4(2) . . ? C6 C5 C4 119.3(3) . . ? C6 C5 H5 120.3 . . ? C4 C5 H5 120.3 . . ? N1 C6 C5 123.2(3) . . ? N1 C6 H6 118.4 . . ? C5 C6 H6 118.4 . . ? C7 N7 H71 116.0(17) . . ? C7 N7 H72 123.9(17) . . ? H71 N7 H72 120(2) . . ? O7 C7 N7 122.8(3) . . ? O7 C7 C4 119.1(2) . . ? N7 C7 C4 118.1(2) . . ? C16 C11 C12 119.4(3) . . ? C16 C11 C17 120.8(2) . . ? C12 C11 C17 119.8(3) . . ? C13 C12 C11 120.6(3) . . ? C13 C12 H12 119.7 . . ? C11 C12 H12 119.7 . . ? C14 C13 C12 118.0(3) . . ? C14 C13 H13 121.0 . . ? C12 C13 H13 121.0 . . ? C13 C14 F14 118.6(3) . . ? C13 C14 C15 123.5(3) . . ? F14 C14 C15 117.9(3) . . ? C14 C15 C16 117.8(3) . . ? C14 C15 H15 121.1 . . ? C16 C15 H15 121.1 . . ? C11 C16 C15 120.6(3) . . ? C11 C16 H16 119.7 . . ? C15 C16 H16 119.7 . . ? C17 O17 H17 111.8(16) . . ? O18 C17 O17 122.7(3) . . ? O18 C17 C11 123.8(2) . . ? O17 C17 C11 113.6(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 N1 C2 C3 0.4(4) . . . . ? N1 C2 C3 C4 -0.7(5) . . . . ? C2 C3 C4 C5 0.7(4) . . . . ? C2 C3 C4 C7 179.4(2) . . . . ? C3 C4 C5 C6 -0.3(4) . . . . ? C7 C4 C5 C6 -179.1(2) . . . . ? C2 N1 C6 C5 0.1(4) . . . . ? C4 C5 C6 N1 -0.1(4) . . . . ? C3 C4 C7 O7 -177.5(3) . . . . ? C5 C4 C7 O7 1.2(4) . . . . ? C3 C4 C7 N7 1.4(4) . . . . ? C5 C4 C7 N7 -179.9(3) . . . . ? C16 C11 C12 C13 -0.6(5) . . . . ? C17 C11 C12 C13 -179.7(3) . . . . ? C11 C12 C13 C14 0.5(5) . . . . ? C12 C13 C14 F14 -179.9(3) . . . . ? C12 C13 C14 C15 -0.2(5) . . . . ? C13 C14 C15 C16 0.0(5) . . . . ? F14 C14 C15 C16 179.7(3) . . . . ? C12 C11 C16 C15 0.4(5) . . . . ? C17 C11 C16 C15 179.5(3) . . . . ? C14 C15 C16 C11 -0.2(5) . . . . ? C16 C11 C17 O18 -176.8(3) . . . . ? C12 C11 C17 O18 2.2(4) . . . . ? C16 C11 C17 O17 3.3(4) . . . . ? C12 C11 C17 O17 -177.6(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O17 H17 N1 1.04(3) 1.57(3) 2.608(3) 173(3) . N7 H72 O18 0.93(3) 2.04(3) 2.964(3) 170(2) 2_645 C3 H3 O18 0.94 2.46 3.378(4) 165.3 2_645 N7 H71 O7 0.91(2) 2.00(3) 2.901(3) 177(2) 5_646 _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 26.55 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.357 _refine_diff_density_min -0.285 _refine_diff_density_rms 0.094 data_4 _database_code_depnum_ccdc_archive 'CCDC 224992' _chemical_name_common '3,5-dinitrobenzamide, 4-(dimethylamino)benzoic acid' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3,5-dinitrobenzamide, 4-(dimethylamino)benzoic acid ; _chemical_melting_point 198-200 _chemical_formula_moiety ; (C7 H5 N3 O5) (C9 H11 N O2) ; _chemical_formula_sum 'C16 H16 N4 O7' _chemical_formula_weight 376.33 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 0.0016 '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 8.0266(14) _cell_length_b 8.5974(16) _cell_length_c 12.514(2) _cell_angle_alpha 84.563(3) _cell_angle_beta 89.934(4) _cell_angle_gamma 75.345(3) _cell_volume 831.5(3) _cell_formula_units_Z 2 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 849 _cell_measurement_theta_min 2.30 _cell_measurement_theta_max 26.25 _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.503 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 392 _exptl_absorpt_coefficient_mu 0.120 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(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 5780 _diffrn_reflns_av_R_equivalents 0.0331 _diffrn_reflns_av_sigmaI/netI 0.1075 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.64 _diffrn_reflns_theta_max 28.24 _reflns_number_total 3682 _reflns_number_gt 1658 _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^)+(0.0550P)^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 3682 _refine_ls_number_parameters 254 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1191 _refine_ls_R_factor_gt 0.0519 _refine_ls_wR_factor_ref 0.1297 _refine_ls_wR_factor_gt 0.1092 _refine_ls_goodness_of_fit_ref 0.810 _refine_ls_restrained_S_all 0.810 _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 0.5830(3) 0.3501(3) 0.3480(2) 0.0280(6) Uani 1 1 d . . . C2 C 0.5668(3) 0.1922(3) 0.3602(2) 0.0284(6) Uani 1 1 d . . . H2 H 0.6136 0.1219 0.4220 0.034 Uiso 1 1 calc R . . O3 O 0.4113(2) -0.0819(2) 0.21834(15) 0.0517(6) Uani 1 1 d . . . C3 C 0.4816(3) 0.1396(3) 0.2809(2) 0.0280(6) Uani 1 1 d . . . N3 N 0.4600(3) -0.0258(3) 0.29501(19) 0.0352(6) Uani 1 1 d . . . O4 O 0.4912(2) -0.0991(2) 0.38521(15) 0.0492(6) Uani 1 1 d . . . C4 C 0.4086(3) 0.2366(3) 0.1910(2) 0.0323(6) Uani 1 1 d . . . H4 H 0.3486 0.1986 0.1379 0.039 Uiso 1 1 calc R . . C5 C 0.4272(3) 0.3929(3) 0.1821(2) 0.0325(6) Uani 1 1 d . . . N5 N 0.3428(3) 0.5019(3) 0.08907(19) 0.0473(6) Uani 1 1 d . . . O5 O 0.2512(3) 0.4543(3) 0.02916(17) 0.0727(7) Uani 1 1 d . . . C6 C 0.5133(3) 0.4509(3) 0.25735(19) 0.0300(6) Uani 1 1 d . . . H6 H 0.5250 0.5585 0.2476 0.036 Uiso 1 1 calc R . . O6 O 0.3701(3) 0.6351(3) 0.07572(18) 0.0803(8) Uani 1 1 d . . . O7 O 0.7251(2) 0.5413(2) 0.39824(13) 0.0369(5) Uani 1 1 d . . . N7 N 0.7020(3) 0.3470(3) 0.52704(18) 0.0336(6) Uani 1 1 d . . . H71 H 0.761(3) 0.397(3) 0.5790(19) 0.040 Uiso 1 1 d . . . H72 H 0.651(3) 0.273(3) 0.553(2) 0.040 Uiso 1 1 d . . . C7 C 0.6756(3) 0.4192(3) 0.4281(2) 0.0298(6) Uani 1 1 d . . . C11 C 0.9601(3) 0.7705(3) 0.68010(19) 0.0279(6) Uani 1 1 d . . . C12 C 0.9584(3) 0.9271(3) 0.6383(2) 0.0321(6) Uani 1 1 d . . . H12 H 0.9111 0.9652 0.5683 0.039 Uiso 1 1 calc R . . C13 C 1.0233(3) 1.0274(3) 0.6958(2) 0.0325(6) Uani 1 1 d . . . H13 H 1.0177 1.1343 0.6657 0.039 Uiso 1 1 calc R . . C14 C 1.0981(3) 0.9746(3) 0.7988(2) 0.0297(6) Uani 1 1 d . A . C15 C 1.0982(3) 0.8166(3) 0.8414(2) 0.0301(6) Uani 1 1 d . . . H15 H 1.1450 0.7775 0.9113 0.036 Uiso 1 1 calc R . . C16 C 1.0310(3) 0.7185(3) 0.7823(2) 0.0307(6) Uani 1 1 d . . . H16 H 1.0332 0.6123 0.8124 0.037 Uiso 1 1 calc R . . N17 N 1.1697(3) 1.0716(3) 0.85434(17) 0.0427(6) Uani 1 1 d . . . C17 C 1.1414(4) 1.2425(3) 0.8198(2) 0.0591(9) Uani 1 1 d . A . H17A H 1.2119 1.2897 0.8647 0.089 Uiso 1 1 calc R . . H17B H 1.0195 1.2969 0.8268 0.089 Uiso 1 1 calc R . . H17C H 1.1738 1.2562 0.7446 0.089 Uiso 1 1 calc R . . C18A C 1.2499(3) 1.0168(3) 0.9603(2) 0.0453(8) Uani 0.63(3) 1 d P A 1 H18A H 1.3392 1.0732 0.9719 0.068 Uiso 0.63(3) 1 calc PR A 1 H18B H 1.3019 0.9002 0.9649 0.068 Uiso 0.63(3) 1 calc PR A 1 H18C H 1.1624 1.0402 1.0153 0.068 Uiso 0.63(3) 1 calc PR A 1 C18B C 1.2499(3) 1.0168(3) 0.9603(2) 0.0453(8) Uani 0.37(3) 1 d P A 2 H18D H 1.3555 0.9314 0.9538 0.068 Uiso 0.37(3) 1 calc PR A 2 H18E H 1.1699 0.9746 1.0069 0.068 Uiso 0.37(3) 1 calc PR A 2 H18F H 1.2781 1.1077 0.9914 0.068 Uiso 0.37(3) 1 calc PR A 2 O19 O 0.8508(2) 0.7213(2) 0.51715(15) 0.0453(5) Uani 1 1 d . . . H19 H 0.805(3) 0.645(3) 0.476(2) 0.054 Uiso 1 1 d . . . C19 C 0.8920(3) 0.6624(3) 0.6179(2) 0.0316(6) Uani 1 1 d . . . O20 O 0.8715(2) 0.5321(2) 0.65538(14) 0.0376(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 0.0265(12) 0.0263(15) 0.0333(15) -0.0020(13) 0.0011(11) -0.0111(12) C2 0.0261(12) 0.0300(15) 0.0287(15) 0.0003(12) 0.0005(11) -0.0077(12) O3 0.0714(14) 0.0457(13) 0.0495(13) -0.0141(11) -0.0061(11) -0.0325(12) C3 0.0314(13) 0.0245(14) 0.0320(15) -0.0030(12) 0.0030(12) -0.0142(12) N3 0.0398(12) 0.0282(13) 0.0430(15) -0.0059(12) 0.0014(12) -0.0176(11) O4 0.0704(14) 0.0348(12) 0.0452(13) 0.0094(10) -0.0085(11) -0.0235(11) C4 0.0341(14) 0.0351(16) 0.0302(15) -0.0063(13) 0.0003(12) -0.0123(13) C5 0.0378(14) 0.0303(16) 0.0294(15) 0.0027(13) -0.0041(12) -0.0105(13) N5 0.0624(16) 0.0382(16) 0.0413(15) 0.0054(13) -0.0124(13) -0.0164(14) O5 0.1036(18) 0.0627(16) 0.0561(14) 0.0102(12) -0.0457(14) -0.0349(15) C6 0.0327(13) 0.0263(15) 0.0333(15) -0.0001(13) 0.0035(12) -0.0130(12) O6 0.135(2) 0.0411(14) 0.0677(16) 0.0199(12) -0.0442(15) -0.0374(15) O7 0.0444(10) 0.0379(12) 0.0361(11) -0.0019(9) -0.0030(9) -0.0248(10) N7 0.0405(13) 0.0321(14) 0.0336(14) 0.0002(11) -0.0044(11) -0.0205(11) C7 0.0251(13) 0.0295(16) 0.0357(16) -0.0018(13) 0.0014(12) -0.0094(12) C11 0.0264(12) 0.0310(15) 0.0287(15) -0.0015(12) -0.0016(11) -0.0122(12) C12 0.0307(13) 0.0386(17) 0.0276(15) 0.0035(13) -0.0044(12) -0.0122(13) C13 0.0347(14) 0.0253(15) 0.0366(16) 0.0055(13) -0.0052(12) -0.0090(12) C14 0.0288(13) 0.0280(15) 0.0330(15) -0.0016(13) -0.0023(12) -0.0089(12) C15 0.0352(14) 0.0289(15) 0.0257(14) 0.0035(12) -0.0031(12) -0.0092(13) C16 0.0324(13) 0.0251(15) 0.0355(16) 0.0021(13) 0.0004(12) -0.0110(12) N17 0.0604(15) 0.0289(13) 0.0394(14) 0.0019(11) -0.0194(12) -0.0142(12) C17 0.086(2) 0.0298(18) 0.066(2) 0.0033(16) -0.0242(19) -0.0240(17) C18A 0.0546(17) 0.0447(18) 0.0403(17) -0.0022(15) -0.0108(15) -0.0203(16) C18B 0.0546(17) 0.0447(18) 0.0403(17) -0.0022(15) -0.0108(15) -0.0203(16) O19 0.0644(13) 0.0492(13) 0.0341(12) 0.0002(10) -0.0080(10) -0.0376(11) C19 0.0254(13) 0.0385(18) 0.0311(16) -0.0010(14) 0.0024(12) -0.0094(13) O20 0.0408(10) 0.0340(11) 0.0419(12) 0.0003(9) -0.0030(9) -0.0178(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 C1 C6 1.386(3) . ? C1 C2 1.390(3) . ? C1 C7 1.499(3) . ? C2 C3 1.379(3) . ? C2 H2 0.9500 . ? O3 N3 1.221(2) . ? C3 C4 1.371(3) . ? C3 N3 1.470(3) . ? N3 O4 1.233(2) . ? C4 C5 1.383(3) . ? C4 H4 0.9500 . ? C5 C6 1.370(3) . ? C5 N5 1.472(3) . ? N5 O6 1.217(3) . ? N5 O5 1.217(3) . ? C6 H6 0.9500 . ? O7 C7 1.239(3) . ? N7 C7 1.324(3) . ? N7 H71 0.99(2) . ? N7 H72 0.87(3) . ? C11 C16 1.388(3) . ? C11 C12 1.394(3) . ? C11 C19 1.471(3) . ? C12 C13 1.371(3) . ? C12 H12 0.9500 . ? C13 C14 1.407(3) . ? C13 H13 0.9500 . ? C14 N17 1.364(3) . ? C14 C15 1.411(3) . ? C15 C16 1.377(3) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? N17 C17 1.452(3) . ? N17 C18A 1.457(3) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18A H18A 0.9800 . ? C18A H18B 0.9800 . ? C18A H18C 0.9800 . ? O19 C19 1.323(3) . ? O19 H19 1.01(3) . ? C19 O20 1.223(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 C6 C1 C2 119.7(2) . . ? C6 C1 C7 117.0(2) . . ? C2 C1 C7 123.4(2) . . ? C3 C2 C1 118.8(2) . . ? C3 C2 H2 120.6 . . ? C1 C2 H2 120.6 . . ? C4 C3 C2 123.2(2) . . ? C4 C3 N3 117.9(2) . . ? C2 C3 N3 118.9(2) . . ? O3 N3 O4 123.9(2) . . ? O3 N3 C3 118.9(2) . . ? O4 N3 C3 117.2(2) . . ? C3 C4 C5 116.3(2) . . ? C3 C4 H4 121.9 . . ? C5 C4 H4 121.9 . . ? C6 C5 C4 123.1(2) . . ? C6 C5 N5 119.5(2) . . ? C4 C5 N5 117.3(2) . . ? O6 N5 O5 123.4(3) . . ? O6 N5 C5 117.7(2) . . ? O5 N5 C5 118.8(2) . . ? C5 C6 C1 119.0(2) . . ? C5 C6 H6 120.5 . . ? C1 C6 H6 120.5 . . ? C7 N7 H71 117.2(14) . . ? C7 N7 H72 123.5(17) . . ? H71 N7 H72 118(2) . . ? O7 C7 N7 122.9(2) . . ? O7 C7 C1 118.3(2) . . ? N7 C7 C1 118.8(2) . . ? C16 C11 C12 117.7(2) . . ? C16 C11 C19 120.8(2) . . ? C12 C11 C19 121.5(2) . . ? C13 C12 C11 121.6(2) . . ? C13 C12 H12 119.2 . . ? C11 C12 H12 119.2 . . ? C12 C13 C14 121.1(2) . . ? C12 C13 H13 119.5 . . ? C14 C13 H13 119.5 . . ? N17 C14 C13 121.3(2) . . ? N17 C14 C15 121.5(2) . . ? C13 C14 C15 117.2(2) . . ? C16 C15 C14 120.6(2) . . ? C16 C15 H15 119.7 . . ? C14 C15 H15 119.7 . . ? C15 C16 C11 121.8(2) . . ? C15 C16 H16 119.1 . . ? C11 C16 H16 119.1 . . ? C14 N17 C17 121.1(2) . . ? C14 N17 C18A 121.6(2) . . ? C17 N17 C18A 116.4(2) . . ? N17 C17 H17A 109.5 . . ? N17 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? N17 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? N17 C18A H18A 109.5 . . ? N17 C18A H18B 109.5 . . ? H18A C18A H18B 109.5 . . ? N17 C18A H18C 109.5 . . ? H18A C18A H18C 109.5 . . ? H18B C18A H18C 109.5 . . ? C19 O19 H19 112.1(15) . . ? O20 C19 O19 122.8(2) . . ? O20 C19 C11 123.8(2) . . ? O19 C19 C11 113.4(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 0.2(3) . . . . ? C7 C1 C2 C3 -178.9(2) . . . . ? C1 C2 C3 C4 -1.3(4) . . . . ? C1 C2 C3 N3 -178.3(2) . . . . ? C4 C3 N3 O3 15.1(3) . . . . ? C2 C3 N3 O3 -167.8(2) . . . . ? C4 C3 N3 O4 -164.2(2) . . . . ? C2 C3 N3 O4 12.9(3) . . . . ? C2 C3 C4 C5 1.2(4) . . . . ? N3 C3 C4 C5 178.1(2) . . . . ? C3 C4 C5 C6 0.1(4) . . . . ? C3 C4 C5 N5 -177.1(2) . . . . ? C6 C5 N5 O6 8.7(4) . . . . ? C4 C5 N5 O6 -174.0(3) . . . . ? C6 C5 N5 O5 -172.1(2) . . . . ? C4 C5 N5 O5 5.2(4) . . . . ? C4 C5 C6 C1 -1.2(4) . . . . ? N5 C5 C6 C1 176.0(2) . . . . ? C2 C1 C6 C5 0.9(3) . . . . ? C7 C1 C6 C5 -179.8(2) . . . . ? C6 C1 C7 O7 -19.0(3) . . . . ? C2 C1 C7 O7 160.2(2) . . . . ? C6 C1 C7 N7 161.5(2) . . . . ? C2 C1 C7 N7 -19.3(3) . . . . ? C16 C11 C12 C13 -0.4(4) . . . . ? C19 C11 C12 C13 -179.4(2) . . . . ? C11 C12 C13 C14 1.5(4) . . . . ? C12 C13 C14 N17 177.1(2) . . . . ? C12 C13 C14 C15 -2.0(4) . . . . ? N17 C14 C15 C16 -177.6(2) . . . . ? C13 C14 C15 C16 1.5(4) . . . . ? C14 C15 C16 C11 -0.5(4) . . . . ? C12 C11 C16 C15 -0.1(3) . . . . ? C19 C11 C16 C15 178.9(2) . . . . ? C13 C14 N17 C17 12.6(4) . . . . ? C15 C14 N17 C17 -168.4(3) . . . . ? C13 C14 N17 C18A -179.0(2) . . . . ? C15 C14 N17 C18A 0.0(4) . . . . ? C16 C11 C19 O20 10.3(4) . . . . ? C12 C11 C19 O20 -170.8(2) . . . . ? C16 C11 C19 O19 -171.2(2) . . . . ? C12 C11 C19 O19 7.7(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N7 H71 O20 0.99(2) 1.95(3) 2.924(3) 167(2) . N7 H72 O4 0.87(3) 2.19(3) 3.063(3) 177(2) 2_656 O19 H19 O7 1.01(3) 1.61(3) 2.618(2) 173(2) . _diffrn_measured_fraction_theta_max 0.893 _diffrn_reflns_theta_full 28.24 _diffrn_measured_fraction_theta_full 0.893 _refine_diff_density_max 0.221 _refine_diff_density_min -0.268 _refine_diff_density_rms 0.055 data_5 _database_code_depnum_ccdc_archive 'CCDC 224993' _chemical_name_common '4-nitrobenzoic acid, 3-(dimethylamino)benzoic acid' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-nitrobenzoic acid, 3-(dimethylamino)benzoic acid ; _chemical_melting_point 163-165 _chemical_formula_moiety ; (C7 H5 N O4) (C9 H11 N O2) ; _chemical_formula_sum 'C16 H16 N2 O6' _chemical_formula_weight 332.31 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 7.1538(13) _cell_length_b 7.9978(15) _cell_length_c 14.315(3) _cell_angle_alpha 91.111(3) _cell_angle_beta 91.483(4) _cell_angle_gamma 111.582(3) _cell_volume 761.0(2) _cell_formula_units_Z 2 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 966 _cell_measurement_theta_min 3.00 _cell_measurement_theta_max 26.35 _exptl_crystal_description plate _exptl_crystal_colour orange-red _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.450 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 348 _exptl_absorpt_coefficient_mu 0.113 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(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 4919 _diffrn_reflns_av_R_equivalents 0.0151 _diffrn_reflns_av_sigmaI/netI 0.0448 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.42 _diffrn_reflns_theta_max 26.37 _reflns_number_total 3060 _reflns_number_gt 1669 _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^)+(0.0600P)^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 3060 _refine_ls_number_parameters 223 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0808 _refine_ls_R_factor_gt 0.0412 _refine_ls_wR_factor_ref 0.1150 _refine_ls_wR_factor_gt 0.0999 _refine_ls_goodness_of_fit_ref 0.859 _refine_ls_restrained_S_all 0.859 _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 0.5013(2) 0.1289(2) 0.60959(12) 0.0308(4) Uani 1 1 d . . . C2 C 0.3948(3) 0.0354(2) 0.68360(13) 0.0383(5) Uani 1 1 d . . . H2 H 0.2590 0.0243 0.6905 0.046 Uiso 1 1 calc R . . C3 C 0.4837(3) -0.0416(2) 0.74718(13) 0.0379(5) Uani 1 1 d . . . H3 H 0.4112 -0.1063 0.7980 0.046 Uiso 1 1 calc R . . C4 C 0.6804(2) -0.0224(2) 0.73518(12) 0.0330(4) Uani 1 1 d . . . C5 C 0.7905(3) 0.0688(2) 0.66235(13) 0.0339(4) Uani 1 1 d . . . H5 H 0.9262 0.0793 0.6559 0.041 Uiso 1 1 calc R . . C6 C 0.6991(2) 0.1445(2) 0.59900(13) 0.0325(4) Uani 1 1 d . . . H6 H 0.7719 0.2077 0.5479 0.039 Uiso 1 1 calc R . . O7 O 0.6773(2) -0.1881(2) 0.86675(10) 0.0568(4) Uani 1 1 d . . . N7 N 0.7775(2) -0.1015(2) 0.80407(11) 0.0393(4) Uani 1 1 d . . . O8 O 0.95535(18) -0.07684(18) 0.79568(10) 0.0492(4) Uani 1 1 d . . . O9 O 0.22312(17) 0.18968(18) 0.54844(9) 0.0468(4) Uani 1 1 d . . . C9 C 0.4027(3) 0.2105(2) 0.54174(13) 0.0339(4) Uani 1 1 d . . . O10 O 0.51357(17) 0.29929(17) 0.47647(9) 0.0392(3) Uani 1 1 d . . . H10 H 0.441(3) 0.341(2) 0.4279(13) 0.047 Uiso 1 1 d . . . C11 C 0.0512(2) 0.4733(2) 0.28487(12) 0.0327(4) Uani 1 1 d . . . C12 C 0.1585(3) 0.5478(2) 0.20762(13) 0.0356(5) Uani 1 1 d . . . H12 H 0.2883 0.5435 0.2004 0.043 Uiso 1 1 calc R . . C13 C 0.0798(3) 0.6295(3) 0.13973(14) 0.0392(5) Uani 1 1 d . . . C14 C -0.1123(3) 0.6312(3) 0.15360(15) 0.0451(5) Uani 1 1 d . . . H14 H -0.1703 0.6861 0.1090 0.054 Uiso 1 1 calc R . . C15 C -0.2188(3) 0.5551(3) 0.23038(15) 0.0462(5) Uani 1 1 d . . . H15 H -0.3495 0.5575 0.2375 0.055 Uiso 1 1 calc R . . C16 C -0.1398(3) 0.4752(3) 0.29750(14) 0.0414(5) Uani 1 1 d . . . H16 H -0.2140 0.4232 0.3506 0.050 Uiso 1 1 calc R . . C17 C 0.1084(3) 0.7885(3) -0.00776(15) 0.0613(6) Uani 1 1 d . . . H17A H 0.1958 0.8140 -0.0614 0.092 Uiso 1 1 calc R . . H17B H 0.1021 0.9011 0.0174 0.092 Uiso 1 1 calc R . . H17C H -0.0271 0.7067 -0.0277 0.092 Uiso 1 1 calc R . . N17 N 0.1885(3) 0.7054(3) 0.06380(13) 0.0684(6) Uani 1 1 d . . . C18 C 0.3849(3) 0.6995(3) 0.05131(15) 0.0653(7) Uani 1 1 d . . . H18A H 0.3803 0.5772 0.0615 0.098 Uiso 1 1 calc R . . H18B H 0.4813 0.7833 0.0963 0.098 Uiso 1 1 calc R . . H18C H 0.4269 0.7338 -0.0124 0.098 Uiso 1 1 calc R . . C19 C 0.1469(2) 0.3967(2) 0.35561(13) 0.0334(4) Uani 1 1 d . . . O19 O 0.32448(17) 0.40725(17) 0.34839(9) 0.0395(3) Uani 1 1 d . . . O20 O 0.03899(19) 0.3193(2) 0.42451(10) 0.0536(4) Uani 1 1 d . . . H20 H 0.110(3) 0.271(3) 0.4667(15) 0.064 Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0328(9) 0.0298(10) 0.0280(10) 0.0000(8) 0.0006(8) 0.0096(8) C2 0.0288(9) 0.0463(12) 0.0401(12) 0.0040(10) 0.0033(8) 0.0138(9) C3 0.0371(10) 0.0429(12) 0.0337(11) 0.0087(9) 0.0051(8) 0.0140(9) C4 0.0373(10) 0.0326(10) 0.0301(11) 0.0004(8) -0.0031(8) 0.0146(8) C5 0.0292(9) 0.0357(11) 0.0367(11) 0.0000(9) 0.0005(8) 0.0120(8) C6 0.0316(9) 0.0331(10) 0.0316(11) 0.0030(8) 0.0023(8) 0.0104(8) O7 0.0596(9) 0.0743(11) 0.0435(9) 0.0264(8) 0.0115(7) 0.0310(8) N7 0.0438(9) 0.0411(10) 0.0360(10) 0.0048(8) -0.0007(8) 0.0193(8) O8 0.0402(8) 0.0595(9) 0.0526(9) 0.0112(7) -0.0027(7) 0.0236(7) O9 0.0358(7) 0.0692(10) 0.0426(9) 0.0162(7) 0.0075(6) 0.0267(7) C9 0.0354(10) 0.0355(11) 0.0313(11) 0.0002(9) 0.0022(8) 0.0134(8) O10 0.0358(7) 0.0496(9) 0.0336(8) 0.0120(7) 0.0008(6) 0.0171(6) C11 0.0317(9) 0.0290(10) 0.0367(12) -0.0015(9) -0.0011(8) 0.0106(8) C12 0.0311(9) 0.0419(12) 0.0360(11) 0.0016(9) -0.0003(8) 0.0162(8) C13 0.0400(10) 0.0428(12) 0.0354(12) 0.0048(9) -0.0021(9) 0.0159(9) C14 0.0429(11) 0.0456(12) 0.0509(14) 0.0040(10) -0.0099(10) 0.0218(10) C15 0.0315(10) 0.0526(13) 0.0575(14) 0.0067(11) 0.0005(9) 0.0190(9) C16 0.0342(10) 0.0439(12) 0.0456(13) 0.0073(10) 0.0031(9) 0.0135(9) C17 0.0725(15) 0.0690(16) 0.0467(14) 0.0188(12) -0.0038(12) 0.0308(13) N17 0.0551(11) 0.1111(17) 0.0513(12) 0.0408(12) 0.0105(9) 0.0429(11) C18 0.0573(13) 0.0960(19) 0.0471(14) 0.0255(13) 0.0168(11) 0.0313(13) C19 0.0340(10) 0.0345(11) 0.0314(11) 0.0018(9) 0.0016(8) 0.0123(8) O19 0.0356(7) 0.0499(8) 0.0373(8) 0.0071(6) 0.0007(6) 0.0204(6) O20 0.0438(8) 0.0770(11) 0.0471(10) 0.0277(8) 0.0098(7) 0.0289(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 C1 C2 1.384(2) . ? C1 C6 1.387(2) . ? C1 C9 1.482(2) . ? C2 C3 1.376(3) . ? C2 H2 0.9500 . ? C3 C4 1.373(2) . ? C3 H3 0.9500 . ? C4 C5 1.375(2) . ? C4 N7 1.472(2) . ? C5 C6 1.378(2) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? O7 N7 1.2210(18) . ? N7 O8 1.2235(17) . ? O9 C9 1.2398(18) . ? C9 O10 1.2869(19) . ? O10 H10 0.99(2) . ? C11 C12 1.379(2) . ? C11 C16 1.388(2) . ? C11 C19 1.472(2) . ? C12 C13 1.398(3) . ? C12 H12 0.9500 . ? C13 N17 1.370(2) . ? C13 C14 1.399(2) . ? C14 C15 1.374(3) . ? C14 H14 0.9500 . ? C15 C16 1.383(3) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 N17 1.448(2) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? N17 C18 1.438(2) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 O19 1.2489(19) . ? C19 O20 1.2899(19) . ? O20 H20 0.95(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 C2 C1 C6 119.84(17) . . ? C2 C1 C9 119.75(15) . . ? C6 C1 C9 120.40(16) . . ? C3 C2 C1 120.56(16) . . ? C3 C2 H2 119.7 . . ? C1 C2 H2 119.7 . . ? C4 C3 C2 118.17(17) . . ? C4 C3 H3 120.9 . . ? C2 C3 H3 120.9 . . ? C3 C4 C5 122.87(17) . . ? C3 C4 N7 118.37(16) . . ? C5 C4 N7 118.76(15) . . ? C4 C5 C6 118.30(16) . . ? C4 C5 H5 120.8 . . ? C6 C5 H5 120.8 . . ? C5 C6 C1 120.25(17) . . ? C5 C6 H6 119.9 . . ? C1 C6 H6 119.9 . . ? O7 N7 O8 123.17(16) . . ? O7 N7 C4 118.65(15) . . ? O8 N7 C4 118.18(15) . . ? O9 C9 O10 123.47(17) . . ? O9 C9 C1 120.60(16) . . ? O10 C9 C1 115.92(15) . . ? C9 O10 H10 114.5(10) . . ? C12 C11 C16 121.14(17) . . ? C12 C11 C19 118.27(15) . . ? C16 C11 C19 120.56(16) . . ? C11 C12 C13 121.21(16) . . ? C11 C12 H12 119.4 . . ? C13 C12 H12 119.4 . . ? N17 C13 C12 120.87(16) . . ? N17 C13 C14 122.09(18) . . ? C12 C13 C14 117.03(17) . . ? C15 C14 C13 121.31(18) . . ? C15 C14 H14 119.3 . . ? C13 C14 H14 119.3 . . ? C14 C15 C16 121.40(17) . . ? C14 C15 H15 119.3 . . ? C16 C15 H15 119.3 . . ? C15 C16 C11 117.91(18) . . ? C15 C16 H16 121.0 . . ? C11 C16 H16 121.0 . . ? N17 C17 H17A 109.5 . . ? N17 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? N17 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C13 N17 C18 120.56(17) . . ? C13 N17 C17 121.61(17) . . ? C18 N17 C17 117.80(17) . . ? N17 C18 H18A 109.5 . . ? N17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? N17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? O19 C19 O20 122.21(16) . . ? O19 C19 C11 120.92(15) . . ? O20 C19 C11 116.87(15) . . ? C19 O20 H20 112.0(12) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 0.3(3) . . . . ? C9 C1 C2 C3 179.87(17) . . . . ? C1 C2 C3 C4 0.2(3) . . . . ? C2 C3 C4 C5 -0.5(3) . . . . ? C2 C3 C4 N7 178.81(16) . . . . ? C3 C4 C5 C6 0.2(3) . . . . ? N7 C4 C5 C6 -179.07(15) . . . . ? C4 C5 C6 C1 0.3(3) . . . . ? C2 C1 C6 C5 -0.6(3) . . . . ? C9 C1 C6 C5 179.86(16) . . . . ? C3 C4 N7 O7 3.3(2) . . . . ? C5 C4 N7 O7 -177.34(17) . . . . ? C3 C4 N7 O8 -176.57(17) . . . . ? C5 C4 N7 O8 2.8(2) . . . . ? C2 C1 C9 O9 -2.9(3) . . . . ? C6 C1 C9 O9 176.61(17) . . . . ? C2 C1 C9 O10 178.16(16) . . . . ? C6 C1 C9 O10 -2.3(2) . . . . ? C16 C11 C12 C13 0.7(3) . . . . ? C19 C11 C12 C13 -177.31(17) . . . . ? C11 C12 C13 N17 179.11(18) . . . . ? C11 C12 C13 C14 -0.3(3) . . . . ? N17 C13 C14 C15 -179.7(2) . . . . ? C12 C13 C14 C15 -0.3(3) . . . . ? C13 C14 C15 C16 0.6(3) . . . . ? C14 C15 C16 C11 -0.2(3) . . . . ? C12 C11 C16 C15 -0.4(3) . . . . ? C19 C11 C16 C15 177.55(17) . . . . ? C12 C13 N17 C18 1.2(3) . . . . ? C14 C13 N17 C18 -179.4(2) . . . . ? C12 C13 N17 C17 179.20(19) . . . . ? C14 C13 N17 C17 -1.4(3) . . . . ? C12 C11 C19 O19 3.7(3) . . . . ? C16 C11 C19 O19 -174.30(17) . . . . ? C12 C11 C19 O20 -176.32(16) . . . . ? C16 C11 C19 O20 5.7(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O10 H10 O19 0.99(2) 1.60(2) 2.5941(18) 179.5(16) . O20 H20 O9 0.95(2) 1.68(2) 2.6288(18) 174.9(19) . C18 H18C O7 0.98 2.44 3.340(2) 151.9 1_564 _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.212 _refine_diff_density_min -0.206 _refine_diff_density_rms 0.045 data_6 _database_code_depnum_ccdc_archive 'CCDC 224994' _chemical_name_common 'pyrazinecarboxamide, 4-nitrobenzamide' _audit_creation_method SHELXL-97 _chemical_name_systematic ; pyrazinecarboxamide, 4-nitrobenzamide ; _chemical_melting_point 148-150 _chemical_formula_moiety ; (C5 H5 N3 O) (C7 H6 N2 O3) ; _chemical_formula_sum 'C12 H11 N5 O4' _chemical_formula_weight 289.26 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 7.6155(7) _cell_length_b 7.6980(9) _cell_length_c 21.587(2) _cell_angle_alpha 95.590(8) _cell_angle_beta 94.719(7) _cell_angle_gamma 90.268(8) _cell_volume 1255.1(2) _cell_formula_units_Z 4 _cell_measurement_temperature 203(2) _cell_measurement_reflns_used 980 _cell_measurement_theta_min 2.70 _cell_measurement_theta_max 26.25 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.531 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 600 _exptl_absorpt_coefficient_mu 0.119 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 203(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 9111 _diffrn_reflns_av_R_equivalents 0.0795 _diffrn_reflns_av_sigmaI/netI 0.1991 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 28.27 _reflns_number_total 5621 _reflns_number_gt 1659 _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^)+(0.0500P)^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 0.0105(11) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5621 _refine_ls_number_parameters 404 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2052 _refine_ls_R_factor_gt 0.0569 _refine_ls_wR_factor_ref 0.1514 _refine_ls_wR_factor_gt 0.1127 _refine_ls_goodness_of_fit_ref 0.777 _refine_ls_restrained_S_all 0.777 _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 C11 C 0.2531(5) 0.4743(4) 0.50382(17) 0.0278(9) Uani 1 1 d . . . C12 C 0.1863(5) 0.4241(5) 0.44377(17) 0.0372(10) Uani 1 1 d . . . H12 H 0.1874 0.3053 0.4287 0.045 Uiso 1 1 calc R . . C13 C 0.1175(5) 0.5433(5) 0.40485(17) 0.0406(11) Uani 1 1 d . . . H13 H 0.0733 0.5081 0.3636 0.049 Uiso 1 1 calc R . . C14 C 0.1160(5) 0.7135(5) 0.42843(18) 0.0320(10) Uani 1 1 d . . . C15 C 0.1772(5) 0.7699(5) 0.48824(18) 0.0418(11) Uani 1 1 d . . . H15 H 0.1741 0.8886 0.5031 0.050 Uiso 1 1 calc R . . C16 C 0.2435(5) 0.6482(5) 0.52603(18) 0.0453(11) Uani 1 1 d . . . H16 H 0.2830 0.6837 0.5678 0.054 Uiso 1 1 calc R . . C17 C 0.3309(5) 0.3512(5) 0.54686(18) 0.0329(10) Uani 1 1 d . . . N17 N 0.3696(5) 0.1922(4) 0.52206(15) 0.0448(10) Uani 1 1 d . . . H171 H 0.432(4) 0.114(4) 0.5543(17) 0.054 Uiso 1 1 d . . . H172 H 0.365(5) 0.176(5) 0.4840(17) 0.054 Uiso 1 1 d . . . O17 O 0.3544(4) 0.3932(3) 0.60306(12) 0.0512(8) Uani 1 1 d . . . N18 N 0.0457(4) 0.8410(4) 0.38632(17) 0.0448(10) Uani 1 1 d . . . O18 O 0.0170(4) 0.7950(4) 0.33085(13) 0.0669(10) Uani 1 1 d . . . O19 O 0.0197(4) 0.9893(4) 0.40862(14) 0.0687(10) Uani 1 1 d . . . C21 C 0.6404(5) -0.1127(4) 0.70794(16) 0.0277(9) Uani 1 1 d . . . C22 C 0.7341(5) -0.0507(5) 0.76319(17) 0.0341(10) Uani 1 1 d . . . H22 H 0.7469 0.0704 0.7738 0.041 Uiso 1 1 calc R . . C23 C 0.8087(5) -0.1637(4) 0.80273(17) 0.0348(10) Uani 1 1 d . . . H23 H 0.8732 -0.1219 0.8403 0.042 Uiso 1 1 calc R . . C24 C 0.7865(5) -0.3404(4) 0.78588(16) 0.0282(9) Uani 1 1 d . . . C25 C 0.6948(5) -0.4060(5) 0.73185(16) 0.0350(10) Uani 1 1 d . . . H25 H 0.6823 -0.5272 0.7215 0.042 Uiso 1 1 calc R . . C26 C 0.6211(5) -0.2909(4) 0.69274(17) 0.0346(10) Uani 1 1 d . . . H26 H 0.5569 -0.3336 0.6553 0.042 Uiso 1 1 calc R . . C27 C 0.5606(5) 0.0067(5) 0.66269(18) 0.0357(10) Uani 1 1 d . . . N27 N 0.5010(4) 0.1588(4) 0.68565(15) 0.0383(9) Uani 1 1 d . . . H271 H 0.438(4) 0.250(4) 0.6516(16) 0.046 Uiso 1 1 d . . . H272 H 0.493(5) 0.181(4) 0.7249(16) 0.046 Uiso 1 1 d . . . O27 O 0.5499(4) -0.0379(3) 0.60627(11) 0.0481(8) Uani 1 1 d . . . N28 N 0.8691(4) -0.4634(4) 0.82746(16) 0.0382(9) Uani 1 1 d . . . O28 O 0.9606(4) -0.4042(3) 0.87397(13) 0.0546(9) Uani 1 1 d . . . O29 O 0.8437(4) -0.6192(3) 0.81375(13) 0.0595(9) Uani 1 1 d . . . N31 N 0.3391(4) 0.7725(4) 0.82119(14) 0.0335(8) Uani 1 1 d . . . C32 C 0.3210(5) 0.6050(4) 0.79824(17) 0.0294(9) Uani 1 1 d . . . C33 C 0.2258(5) 0.5571(5) 0.74223(17) 0.0352(10) Uani 1 1 d . . . H33 H 0.2141 0.4377 0.7284 0.042 Uiso 1 1 calc R . . N34 N 0.1500(4) 0.6710(4) 0.70689(14) 0.0384(9) Uani 1 1 d . . . C35 C 0.1708(5) 0.8378(5) 0.72885(18) 0.0381(10) Uani 1 1 d . . . H35 H 0.1215 0.9244 0.7052 0.046 Uiso 1 1 calc R . . C36 C 0.2629(5) 0.8866(5) 0.78544(17) 0.0349(10) Uani 1 1 d . . . H36 H 0.2723 1.0060 0.7995 0.042 Uiso 1 1 calc R . . C37 C 0.4079(5) 0.4729(4) 0.83563(17) 0.0299(9) Uani 1 1 d . . . N37 N 0.4810(5) 0.5288(4) 0.89161(15) 0.0437(10) Uani 1 1 d . . . H371 H 0.546(5) 0.447(5) 0.9188(16) 0.052 Uiso 1 1 d . . . H372 H 0.470(4) 0.654(4) 0.9053(16) 0.052 Uiso 1 1 d . . . O37 O 0.4084(3) 0.3169(3) 0.81408(11) 0.0400(7) Uani 1 1 d . . . N41 N 0.7004(4) -0.1587(4) 0.97146(13) 0.0330(8) Uani 1 1 d . . . C42 C 0.7295(5) 0.0099(4) 0.99046(17) 0.0280(9) Uani 1 1 d . . . C43 C 0.8312(5) 0.0621(5) 1.04480(17) 0.0323(10) Uani 1 1 d . . . H43 H 0.8459 0.1823 1.0567 0.039 Uiso 1 1 calc R . . N44 N 0.9097(4) -0.0488(4) 1.08127(13) 0.0367(8) Uani 1 1 d . . . C45 C 0.8812(5) -0.2173(5) 1.06184(18) 0.0386(11) Uani 1 1 d . . . H45 H 0.9334 -0.3021 1.0857 0.046 Uiso 1 1 calc R . . C46 C 0.7778(5) -0.2705(5) 1.00796(17) 0.0356(10) Uani 1 1 d . . . H46 H 0.7611 -0.3908 0.9965 0.043 Uiso 1 1 calc R . . C47 C 0.6508(5) 0.1424(5) 0.95150(17) 0.0294(9) Uani 1 1 d . . . N47 N 0.5569(4) 0.0809(4) 0.89903(15) 0.0351(9) Uani 1 1 d . . . H471 H 0.513(4) 0.179(4) 0.8706(15) 0.042 Uiso 1 1 d . . . H472 H 0.547(4) -0.033(4) 0.8923(15) 0.042 Uiso 1 1 d . . . O47 O 0.6710(3) 0.2983(3) 0.96792(12) 0.0428(8) 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 C11 0.030(2) 0.030(2) 0.025(2) 0.0055(17) 0.0050(18) 0.0016(17) C12 0.052(3) 0.029(2) 0.029(2) -0.0006(18) -0.003(2) 0.0025(19) C13 0.054(3) 0.036(2) 0.030(2) 0.0018(19) -0.003(2) 0.007(2) C14 0.032(2) 0.031(2) 0.033(2) 0.0076(19) -0.0026(19) 0.0050(19) C15 0.052(3) 0.032(2) 0.038(3) -0.0073(19) -0.006(2) 0.001(2) C16 0.055(3) 0.040(2) 0.038(3) 0.000(2) -0.010(2) 0.004(2) C17 0.036(3) 0.034(2) 0.029(2) 0.0067(19) 0.004(2) 0.0059(19) N17 0.068(3) 0.037(2) 0.029(2) 0.0016(18) 0.001(2) 0.0155(18) O17 0.082(2) 0.0445(17) 0.0260(16) 0.0019(14) -0.0024(16) 0.0181(15) N18 0.051(2) 0.039(2) 0.046(2) 0.0073(19) 0.008(2) 0.0016(18) O18 0.105(3) 0.059(2) 0.0352(19) 0.0069(16) -0.0070(19) 0.0088(18) O19 0.105(3) 0.0387(18) 0.062(2) 0.0069(17) -0.0012(19) 0.0222(17) C21 0.029(2) 0.030(2) 0.023(2) -0.0010(17) 0.0026(18) -0.0012(18) C22 0.038(3) 0.033(2) 0.031(2) -0.0023(18) 0.006(2) -0.0012(19) C23 0.039(3) 0.036(2) 0.030(2) 0.0045(19) 0.004(2) 0.0004(19) C24 0.030(2) 0.028(2) 0.027(2) 0.0072(18) 0.0008(18) 0.0000(17) C25 0.044(3) 0.033(2) 0.027(2) 0.0000(18) -0.0029(19) 0.0015(19) C26 0.037(3) 0.038(2) 0.027(2) -0.0035(19) 0.0003(19) -0.0021(19) C27 0.037(3) 0.038(2) 0.032(3) 0.004(2) 0.005(2) 0.0022(19) N27 0.057(2) 0.0337(19) 0.0237(19) 0.0016(16) 0.0008(18) 0.0103(17) O27 0.073(2) 0.0470(17) 0.0241(15) 0.0009(13) 0.0047(15) 0.0180(15) N28 0.035(2) 0.036(2) 0.043(2) 0.0082(18) 0.0005(18) 0.0009(17) O28 0.059(2) 0.0505(18) 0.051(2) 0.0045(16) -0.0197(17) -0.0017(15) O29 0.084(2) 0.0283(16) 0.062(2) 0.0055(15) -0.0214(18) -0.0012(15) N31 0.035(2) 0.0285(18) 0.036(2) 0.0003(15) 0.0033(16) 0.0013(15) C32 0.032(2) 0.028(2) 0.028(2) 0.0039(18) 0.0020(18) -0.0002(18) C33 0.036(3) 0.036(2) 0.031(2) -0.0026(19) -0.004(2) 0.0009(19) N34 0.031(2) 0.042(2) 0.040(2) 0.0003(17) -0.0041(16) 0.0033(16) C35 0.036(3) 0.038(2) 0.039(3) 0.006(2) -0.001(2) 0.002(2) C36 0.034(3) 0.032(2) 0.038(3) 0.0037(19) 0.001(2) 0.0031(19) C37 0.038(2) 0.026(2) 0.024(2) 0.0009(17) -0.0011(18) -0.0005(18) N37 0.070(3) 0.027(2) 0.031(2) -0.0002(16) -0.0088(19) 0.0033(18) O37 0.0572(19) 0.0257(14) 0.0345(16) -0.0015(13) -0.0058(14) 0.0032(13) N41 0.037(2) 0.0275(18) 0.034(2) 0.0018(15) 0.0021(16) -0.0006(15) C42 0.026(2) 0.030(2) 0.029(2) 0.0027(18) 0.0018(18) -0.0019(17) C43 0.036(2) 0.031(2) 0.029(2) 0.0009(18) -0.0006(19) 0.0008(18) N44 0.042(2) 0.038(2) 0.030(2) 0.0065(16) -0.0045(16) 0.0028(16) C45 0.040(3) 0.035(2) 0.041(3) 0.008(2) -0.001(2) 0.004(2) C46 0.042(3) 0.032(2) 0.034(2) 0.0071(19) 0.002(2) 0.0052(19) C47 0.031(2) 0.031(2) 0.027(2) 0.0033(18) 0.0024(19) 0.0006(18) N47 0.045(2) 0.0251(18) 0.033(2) 0.0022(16) -0.0041(17) -0.0024(17) O47 0.058(2) 0.0207(14) 0.0468(18) 0.0035(13) -0.0116(15) -0.0043(13) _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 C11 C12 1.371(5) . ? C11 C16 1.381(4) . ? C11 C17 1.483(5) . ? C12 C13 1.380(5) . ? C12 H12 0.9400 . ? C13 C14 1.359(4) . ? C13 H13 0.9400 . ? C14 C15 1.365(5) . ? C14 N18 1.474(4) . ? C15 C16 1.372(5) . ? C15 H15 0.9400 . ? C16 H16 0.9400 . ? C17 O17 1.223(4) . ? C17 N17 1.332(4) . ? N17 H171 1.05(4) . ? N17 H172 0.82(4) . ? N18 O18 1.217(4) . ? N18 O19 1.219(4) . ? C21 C22 1.381(4) . ? C21 C26 1.383(4) . ? C21 C27 1.500(5) . ? C22 C23 1.370(4) . ? C22 H22 0.9400 . ? C23 C24 1.380(4) . ? C23 H23 0.9400 . ? C24 C25 1.360(4) . ? C24 N28 1.475(4) . ? C25 C26 1.373(4) . ? C25 H25 0.9400 . ? C26 H26 0.9400 . ? C27 O27 1.229(4) . ? C27 N27 1.324(4) . ? N27 H271 1.14(3) . ? N27 H272 0.86(3) . ? N28 O29 1.218(4) . ? N28 O28 1.222(4) . ? N31 C36 1.329(4) . ? N31 C32 1.338(4) . ? C32 C33 1.375(5) . ? C32 C37 1.484(4) . ? C33 N34 1.321(4) . ? C33 H33 0.9400 . ? N34 C35 1.329(4) . ? C35 C36 1.376(5) . ? C35 H35 0.9400 . ? C36 H36 0.9400 . ? C37 O37 1.245(4) . ? C37 N37 1.319(4) . ? N37 H371 1.01(4) . ? N37 H372 0.99(3) . ? N41 C46 1.330(4) . ? N41 C42 1.335(4) . ? C42 C43 1.376(5) . ? C42 C47 1.482(5) . ? C43 N44 1.328(4) . ? C43 H43 0.9400 . ? N44 C45 1.335(4) . ? C45 C46 1.376(5) . ? C45 H45 0.9400 . ? C46 H46 0.9400 . ? C47 O47 1.223(4) . ? C47 N47 1.333(4) . ? N47 H471 1.06(3) . ? N47 H472 0.88(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 C12 C11 C16 118.4(4) . . ? C12 C11 C17 123.5(3) . . ? C16 C11 C17 118.1(3) . . ? C11 C12 C13 121.7(3) . . ? C11 C12 H12 119.1 . . ? C13 C12 H12 119.1 . . ? C14 C13 C12 117.5(4) . . ? C14 C13 H13 121.2 . . ? C12 C13 H13 121.2 . . ? C13 C14 C15 123.1(4) . . ? C13 C14 N18 117.4(3) . . ? C15 C14 N18 119.5(3) . . ? C14 C15 C16 118.1(4) . . ? C14 C15 H15 121.0 . . ? C16 C15 H15 121.0 . . ? C15 C16 C11 121.1(4) . . ? C15 C16 H16 119.4 . . ? C11 C16 H16 119.4 . . ? O17 C17 N17 121.6(4) . . ? O17 C17 C11 121.1(3) . . ? N17 C17 C11 117.4(3) . . ? C17 N17 H171 113.8(18) . . ? C17 N17 H172 117(3) . . ? H171 N17 H172 127(3) . . ? O18 N18 O19 122.5(4) . . ? O18 N18 C14 119.1(3) . . ? O19 N18 C14 118.4(3) . . ? C22 C21 C26 119.4(4) . . ? C22 C21 C27 122.3(3) . . ? C26 C21 C27 118.3(3) . . ? C23 C22 C21 120.7(4) . . ? C23 C22 H22 119.7 . . ? C21 C22 H22 119.7 . . ? C22 C23 C24 118.1(4) . . ? C22 C23 H23 120.9 . . ? C24 C23 H23 120.9 . . ? C25 C24 C23 122.7(4) . . ? C25 C24 N28 118.6(3) . . ? C23 C24 N28 118.6(3) . . ? C24 C25 C26 118.4(3) . . ? C24 C25 H25 120.8 . . ? C26 C25 H25 120.8 . . ? C25 C26 C21 120.7(3) . . ? C25 C26 H26 119.7 . . ? C21 C26 H26 119.7 . . ? O27 C27 N27 121.7(4) . . ? O27 C27 C21 120.4(3) . . ? N27 C27 C21 117.9(3) . . ? C27 N27 H271 118.4(16) . . ? C27 N27 H272 121(2) . . ? H271 N27 H272 120(3) . . ? O29 N28 O28 123.0(4) . . ? O29 N28 C24 118.5(3) . . ? O28 N28 C24 118.5(3) . . ? C36 N31 C32 115.3(3) . . ? N31 C32 C33 121.3(4) . . ? N31 C32 C37 117.4(3) . . ? C33 C32 C37 121.3(3) . . ? N34 C33 C32 123.1(3) . . ? N34 C33 H33 118.4 . . ? C32 C33 H33 118.4 . . ? C33 N34 C35 115.8(3) . . ? N34 C35 C36 121.5(4) . . ? N34 C35 H35 119.3 . . ? C36 C35 H35 119.3 . . ? N31 C36 C35 123.0(4) . . ? N31 C36 H36 118.5 . . ? C35 C36 H36 118.5 . . ? O37 C37 N37 122.9(4) . . ? O37 C37 C32 120.0(3) . . ? N37 C37 C32 117.0(3) . . ? C37 N37 H371 121(2) . . ? C37 N37 H372 117(2) . . ? H371 N37 H372 122(3) . . ? C46 N41 C42 115.6(3) . . ? N41 C42 C43 121.4(4) . . ? N41 C42 C47 118.7(3) . . ? C43 C42 C47 119.9(3) . . ? N44 C43 C42 123.4(3) . . ? N44 C43 H43 118.3 . . ? C42 C43 H43 118.3 . . ? C43 N44 C45 115.0(3) . . ? N44 C45 C46 122.0(4) . . ? N44 C45 H45 119.0 . . ? C46 C45 H45 119.0 . . ? N41 C46 C45 122.7(4) . . ? N41 C46 H46 118.7 . . ? C45 C46 H46 118.7 . . ? O47 C47 N47 123.1(4) . . ? O47 C47 C42 120.8(3) . . ? N47 C47 C42 116.1(3) . . ? C47 N47 H471 113.8(18) . . ? C47 N47 H472 116(2) . . ? H471 N47 H472 130(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C16 C11 C12 C13 2.8(6) . . . . ? C17 C11 C12 C13 -178.9(4) . . . . ? C11 C12 C13 C14 -0.8(6) . . . . ? C12 C13 C14 C15 -0.6(6) . . . . ? C12 C13 C14 N18 178.8(3) . . . . ? C13 C14 C15 C16 0.1(6) . . . . ? N18 C14 C15 C16 -179.3(3) . . . . ? C14 C15 C16 C11 1.9(6) . . . . ? C12 C11 C16 C15 -3.3(6) . . . . ? C17 C11 C16 C15 178.3(4) . . . . ? C12 C11 C17 O17 -164.3(4) . . . . ? C16 C11 C17 O17 14.0(5) . . . . ? C12 C11 C17 N17 13.9(6) . . . . ? C16 C11 C17 N17 -167.8(4) . . . . ? C13 C14 N18 O18 -10.8(5) . . . . ? C15 C14 N18 O18 168.7(4) . . . . ? C13 C14 N18 O19 169.7(4) . . . . ? C15 C14 N18 O19 -10.8(5) . . . . ? C26 C21 C22 C23 0.3(5) . . . . ? C27 C21 C22 C23 -178.4(3) . . . . ? C21 C22 C23 C24 -0.3(5) . . . . ? C22 C23 C24 C25 0.3(5) . . . . ? C22 C23 C24 N28 178.8(3) . . . . ? C23 C24 C25 C26 -0.2(6) . . . . ? N28 C24 C25 C26 -178.7(3) . . . . ? C24 C25 C26 C21 0.2(5) . . . . ? C22 C21 C26 C25 -0.3(5) . . . . ? C27 C21 C26 C25 178.6(3) . . . . ? C22 C21 C27 O27 147.1(4) . . . . ? C26 C21 C27 O27 -31.7(5) . . . . ? C22 C21 C27 N27 -33.7(5) . . . . ? C26 C21 C27 N27 147.5(3) . . . . ? C25 C24 N28 O29 -4.2(5) . . . . ? C23 C24 N28 O29 177.2(3) . . . . ? C25 C24 N28 O28 175.4(4) . . . . ? C23 C24 N28 O28 -3.1(5) . . . . ? C36 N31 C32 C33 -1.6(5) . . . . ? C36 N31 C32 C37 178.4(3) . . . . ? N31 C32 C33 N34 1.6(6) . . . . ? C37 C32 C33 N34 -178.4(3) . . . . ? C32 C33 N34 C35 -0.1(5) . . . . ? C33 N34 C35 C36 -1.2(5) . . . . ? C32 N31 C36 C35 0.3(5) . . . . ? N34 C35 C36 N31 1.2(6) . . . . ? N31 C32 C37 O37 -173.8(3) . . . . ? C33 C32 C37 O37 6.1(5) . . . . ? N31 C32 C37 N37 6.8(5) . . . . ? C33 C32 C37 N37 -173.2(4) . . . . ? C46 N41 C42 C43 -0.8(5) . . . . ? C46 N41 C42 C47 178.7(3) . . . . ? N41 C42 C43 N44 1.3(6) . . . . ? C47 C42 C43 N44 -178.2(3) . . . . ? C42 C43 N44 C45 -0.8(5) . . . . ? C43 N44 C45 C46 -0.1(5) . . . . ? C42 N41 C46 C45 0.0(5) . . . . ? N44 C45 C46 N41 0.5(6) . . . . ? N41 C42 C47 O47 178.4(3) . . . . ? C43 C42 C47 O47 -2.1(5) . . . . ? N41 C42 C47 N47 -0.8(5) . . . . ? C43 C42 C47 N47 178.8(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N17 H171 O27 1.05(4) 1.88(4) 2.927(4) 175(3) . N17 H172 O27 0.82(4) 2.27(4) 3.018(4) 152(4) 2_656 N27 H271 O17 1.14(3) 1.69(3) 2.828(4) 177(3) . N27 H272 O37 0.86(3) 2.24(3) 3.056(4) 159(3) . N37 H371 O47 1.01(4) 1.85(4) 2.856(4) 179(3) . N47 H471 O37 1.06(3) 1.83(3) 2.876(4) 169(3) . N47 H472 N31 0.88(3) 2.49(3) 3.153(4) 132(3) 1_545 C13 H13 N34 0.94 2.50 3.328(5) 147.0 2_566 N37 H372 N41 0.99(3) 2.52(3) 3.198(4) 126(3) 1_565 _diffrn_measured_fraction_theta_max 0.901 _diffrn_reflns_theta_full 28.27 _diffrn_measured_fraction_theta_full 0.901 _refine_diff_density_max 0.266 _refine_diff_density_min -0.265 _refine_diff_density_rms 0.061