data_ord42a _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-aminobenzoic acid/4-hydroxy 3-nitrobenzoic acid co-crystal ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C7 H7 N O2, C7 H5 N O5' _chemical_formula_sum 'C14 H12 N2 O7' _chemical_formula_weight 320.26 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 monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.0165(7) _cell_length_b 16.5146(12) _cell_length_c 9.4128(7) _cell_angle_alpha 90.00 _cell_angle_beta 102.349(7) _cell_angle_gamma 90.00 _cell_volume 1369.17(18) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1867 _cell_measurement_theta_min 2.8335 _cell_measurement_theta_max 28.5745 _exptl_crystal_description Block _exptl_crystal_colour orange _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.554 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 664 _exptl_absorpt_coefficient_mu 0.127 _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 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Goniometer KM4/Xcalibur, detector: Sapphire2 (' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8.3367 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4999 _diffrn_reflns_av_R_equivalents 0.0267 _diffrn_reflns_av_sigmaI/netI 0.0537 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.74 _diffrn_reflns_theta_max 25.35 _reflns_number_total 2493 _reflns_number_gt 1544 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.31 (release 08-01-2009 CrysAlis171 .NET) (compiled Jan 8 2009,16:24:04) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.31 (release 08-01-2009 CrysAlis171 .NET) (compiled Jan 8 2009,16:24:04) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.31 (release 08-01-2009 CrysAlis171 .NET) (compiled Jan 8 2009,16:24:04) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'CrystalMaker' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0372P)^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 2493 _refine_ls_number_parameters 228 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0622 _refine_ls_R_factor_gt 0.0343 _refine_ls_wR_factor_ref 0.0743 _refine_ls_wR_factor_gt 0.0698 _refine_ls_goodness_of_fit_ref 0.817 _refine_ls_restrained_S_all 0.817 _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 0.9511(2) 0.40101(11) 0.16396(18) 0.0207(4) Uani 1 1 d . . . C12 C 1.00756(19) 0.31829(10) 0.18900(17) 0.0170(4) Uani 1 1 d . . . C13 C 1.15671(19) 0.30012(10) 0.26001(17) 0.0198(4) Uani 1 1 d . . . H13 H 1.2244 0.3419 0.2937 0.024 Uiso 1 1 calc R . . C14 C 1.20362(19) 0.22128(11) 0.28025(17) 0.0206(4) Uani 1 1 d . . . H14 H 1.3031 0.2102 0.3275 0.025 Uiso 1 1 calc R . . C15 C 1.1046(2) 0.15718(10) 0.23116(18) 0.0196(4) Uani 1 1 d . . . C16 C 0.95526(19) 0.17540(10) 0.15940(18) 0.0201(4) Uani 1 1 d . . . H16 H 0.8876 0.1338 0.1248 0.024 Uiso 1 1 calc R . . C17 C 0.9091(2) 0.25443(10) 0.14033(18) 0.0185(4) Uani 1 1 d . . . H17 H 0.8095 0.2657 0.0937 0.022 Uiso 1 1 calc R . . O11 O 0.81571(14) 0.41618(7) 0.11054(13) 0.0275(3) Uani 1 1 d . . . O12 O 1.05236(14) 0.45922(8) 0.20196(13) 0.0262(3) Uani 1 1 d . . . H121 H 1.008(2) 0.5133(14) 0.183(2) 0.058(7) Uiso 1 1 d . . . N11 N 1.1537(2) 0.07875(10) 0.24517(19) 0.0292(4) Uani 1 1 d . . . H111 H 1.237(2) 0.0688(12) 0.305(2) 0.048(7) Uiso 1 1 d . . . H112 H 1.083(2) 0.0376(11) 0.2218(19) 0.033(6) Uiso 1 1 d . . . C21 C 1.2023(2) 0.38273(10) -0.08454(17) 0.0203(4) Uani 1 1 d . . . O21 O 1.06604(14) 0.39436(7) -0.13709(12) 0.0253(3) Uani 1 1 d . . . O22 O 1.30224(14) 0.44109(8) -0.05282(14) 0.0288(3) Uani 1 1 d . . . H221 H 1.253(2) 0.4941(13) -0.080(2) 0.060(7) Uiso 1 1 d . . . C22 C 1.26596(19) 0.30053(10) -0.05410(17) 0.0187(4) Uani 1 1 d . . . C23 C 1.1757(2) 0.23408(10) -0.09428(17) 0.0189(4) Uani 1 1 d . . . H23 H 1.0741 0.2409 -0.1393 0.023 Uiso 1 1 calc R . . C24 C 1.2351(2) 0.15675(10) -0.06816(18) 0.0175(4) Uani 1 1 d . . . N21 N 1.13713(17) 0.08846(9) -0.11510(15) 0.0228(4) Uani 1 1 d . . . O23 O 1.00369(14) 0.10044(7) -0.17465(13) 0.0315(3) Uani 1 1 d . . . O24 O 1.19040(15) 0.01873(7) -0.09620(13) 0.0306(3) Uani 1 1 d . . . C25 C 1.3868(2) 0.14477(10) 0.00300(17) 0.0192(4) Uani 1 1 d . . . O25 O 1.45302(15) 0.07250(8) 0.03317(13) 0.0261(3) Uani 1 1 d . . . H25 H 1.380(2) 0.0356(12) 0.001(2) 0.054(7) Uiso 1 1 d . . . C26 C 1.47637(19) 0.21303(10) 0.04420(17) 0.0204(4) Uani 1 1 d . . . H26 H 1.5771 0.2066 0.0923 0.024 Uiso 1 1 calc R . . C27 C 1.4190(2) 0.28937(10) 0.01531(17) 0.0194(4) Uani 1 1 d . . . H27 H 1.4815 0.3341 0.0417 0.023 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 C11 0.0223(11) 0.0210(11) 0.0200(10) -0.0030(8) 0.0070(8) -0.0025(9) C12 0.0194(10) 0.0161(10) 0.0166(9) -0.0002(7) 0.0066(7) -0.0002(8) C13 0.0199(10) 0.0202(10) 0.0200(9) -0.0021(7) 0.0058(7) -0.0043(8) C14 0.0166(10) 0.0262(11) 0.0187(9) 0.0019(8) 0.0029(7) 0.0022(8) C15 0.0251(11) 0.0183(10) 0.0175(9) 0.0035(7) 0.0093(8) 0.0034(8) C16 0.0202(11) 0.0178(11) 0.0229(10) -0.0020(7) 0.0060(8) -0.0040(8) C17 0.0165(11) 0.0206(11) 0.0188(9) 0.0015(8) 0.0045(7) 0.0005(8) O11 0.0209(7) 0.0186(7) 0.0413(8) 0.0020(6) 0.0032(6) 0.0027(6) O12 0.0236(8) 0.0159(7) 0.0381(8) -0.0012(6) 0.0042(6) -0.0022(6) N11 0.0256(10) 0.0205(10) 0.0400(10) 0.0031(8) 0.0033(8) 0.0058(9) C21 0.0261(12) 0.0184(10) 0.0172(9) -0.0010(7) 0.0065(8) -0.0016(9) O21 0.0248(8) 0.0193(7) 0.0301(7) 0.0015(6) 0.0022(5) 0.0030(6) O22 0.0270(8) 0.0143(7) 0.0432(8) 0.0027(6) 0.0035(6) -0.0002(7) C22 0.0217(11) 0.0171(10) 0.0183(9) 0.0008(7) 0.0067(7) 0.0019(8) C23 0.0183(10) 0.0194(10) 0.0196(10) 0.0012(7) 0.0051(7) -0.0004(8) C24 0.0198(10) 0.0148(10) 0.0190(9) -0.0016(7) 0.0065(7) -0.0021(8) N21 0.0253(10) 0.0198(10) 0.0233(8) -0.0010(6) 0.0054(7) -0.0014(8) O23 0.0220(8) 0.0281(8) 0.0411(8) -0.0016(6) -0.0010(6) -0.0032(6) O24 0.0336(8) 0.0134(7) 0.0425(8) -0.0007(6) 0.0028(6) 0.0010(6) C25 0.0237(11) 0.0171(10) 0.0192(9) 0.0002(8) 0.0096(8) 0.0039(9) O25 0.0246(8) 0.0174(7) 0.0350(7) -0.0014(6) 0.0035(6) 0.0029(6) C26 0.0172(10) 0.0217(10) 0.0227(10) -0.0013(8) 0.0054(7) -0.0003(8) C27 0.0216(10) 0.0187(10) 0.0194(9) -0.0009(8) 0.0079(7) -0.0044(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 C11 O11 1.242(2) . ? C11 O12 1.321(2) . ? C11 C12 1.459(2) . ? C12 C17 1.392(2) . ? C12 C13 1.400(2) . ? C13 C14 1.370(2) . ? C13 H13 0.9300 . ? C14 C15 1.398(2) . ? C14 H14 0.9300 . ? C15 N11 1.366(2) . ? C15 C16 1.404(2) . ? C16 C17 1.370(2) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? O12 H121 0.98(2) . ? N11 H111 0.85(2) . ? N11 H112 0.926(19) . ? C21 O21 1.237(2) . ? C21 O22 1.310(2) . ? C21 C22 1.478(2) . ? O22 H221 0.99(2) . ? C22 C23 1.370(2) . ? C22 C27 1.407(2) . ? C23 C24 1.387(2) . ? C23 H23 0.9300 . ? C24 C25 1.402(2) . ? C24 N21 1.442(2) . ? N21 O23 1.2299(18) . ? N21 O24 1.2459(18) . ? C25 O25 1.338(2) . ? C25 C26 1.393(2) . ? O25 H25 0.90(2) . ? C26 C27 1.368(2) . ? C26 H26 0.9300 . ? C27 H27 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O11 C11 O12 121.69(16) . . ? O11 C11 C12 122.20(16) . . ? O12 C11 C12 116.11(15) . . ? C17 C12 C13 118.35(15) . . ? C17 C12 C11 118.69(15) . . ? C13 C12 C11 122.96(15) . . ? C14 C13 C12 120.43(16) . . ? C14 C13 H13 119.8 . . ? C12 C13 H13 119.8 . . ? C13 C14 C15 121.15(16) . . ? C13 C14 H14 119.4 . . ? C15 C14 H14 119.4 . . ? N11 C15 C14 120.98(16) . . ? N11 C15 C16 120.52(17) . . ? C14 C15 C16 118.41(15) . . ? C17 C16 C15 120.05(16) . . ? C17 C16 H16 120.0 . . ? C15 C16 H16 120.0 . . ? C16 C17 C12 121.60(16) . . ? C16 C17 H17 119.2 . . ? C12 C17 H17 119.2 . . ? C11 O12 H121 112.3(12) . . ? C15 N11 H111 117.9(14) . . ? C15 N11 H112 118.7(11) . . ? H111 N11 H112 118.8(18) . . ? O21 C21 O22 123.57(16) . . ? O21 C21 C22 122.11(16) . . ? O22 C21 C22 114.31(16) . . ? C21 O22 H221 110.0(12) . . ? C23 C22 C27 119.28(15) . . ? C23 C22 C21 119.91(15) . . ? C27 C22 C21 120.81(16) . . ? C22 C23 C24 120.29(16) . . ? C22 C23 H23 119.9 . . ? C24 C23 H23 119.9 . . ? C23 C24 C25 121.00(16) . . ? C23 C24 N21 118.54(16) . . ? C25 C24 N21 120.46(15) . . ? O23 N21 O24 121.56(14) . . ? O23 N21 C24 119.29(15) . . ? O24 N21 C24 119.14(14) . . ? O25 C25 C26 117.18(15) . . ? O25 C25 C24 124.96(16) . . ? C26 C25 C24 117.86(15) . . ? C25 O25 H25 105.7(13) . . ? C27 C26 C25 121.23(16) . . ? C27 C26 H26 119.4 . . ? C25 C26 H26 119.4 . . ? C26 C27 C22 120.31(16) . . ? C26 C27 H27 119.8 . . ? C22 C27 H27 119.8 . . ? 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 O12 H121 O21 0.98(2) 1.68(2) 2.6610(17) 175.8(18) 3_765 N11 H111 O12 0.85(2) 2.63(2) 3.256(2) 130.9(17) 2_745 N11 H112 O23 0.926(19) 2.420(19) 3.288(2) 156.1(15) 3_755 O22 H221 O11 0.99(2) 1.61(2) 2.5953(17) 174.3(19) 3_765 O25 H25 O24 0.90(2) 1.78(2) 2.5779(18) 146.2(19) . O25 H25 N21 0.90(2) 2.39(2) 2.903(2) 116.0(16) . _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.208 _refine_diff_density_min -0.182 _refine_diff_density_rms 0.043