data_kra008 _database_code_CSD 166845 _journal_coden_Cambridge 188 _publ_requested_journal 'Perkin Transactions 2' loop_ _publ_author_name 'Griesbeck, Axel G.' 'Haeuseler, Andreas' 'Inoue, Yoshihisa' 'Lex, Johann' 'Oelgemoller, Michael' 'Schmittel, Michael' _publ_contact_author_name 'Prof Michael Schmittel' _publ_contact_author_address ; Universitat Siegen Adolf-Reichwein-Str.; Siegen D-57068 GERMANY ; _publ_contact_author_email 'SCHMITTEL@CHEMIE.UNI-SIEGEN.DE' _publ_section_title ; Hydrogen Bonding in Phthalimido Carboxylic Acids: Cyclic Voltammography Study and Correlation with Photochemical Reactivity. Part 2. 1 Aliphatic and Aromatic Acids. ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-benzoic acid ; _chemical_name_common ? _chemical_melting_point 216-218 C _chemical_formula_moiety ? _chemical_formula_sum 'C15 H9 N O4' _chemical_formula_weight 267.23 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, z+1/2' '-x, -y, -z' '-x-1/2, y-1/2, -z-1/2' _cell_length_a 12.528(1) _cell_length_b 7.897(1) _cell_length_c 12.892(1) _cell_angle_alpha 90.00 _cell_angle_beta 103.19(1) _cell_angle_gamma 90.00 _cell_volume 1241.8(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2725 _cell_measurement_theta_min 3.05 _cell_measurement_theta_max 27.10 _exptl_crystal_description prism _exptl_crystal_colour colourless _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 1.429 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 0.106 _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 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'Phi/Omega-Scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5224 _diffrn_reflns_av_R_equivalents 0.0196 _diffrn_reflns_av_sigmaI/netI 0.0306 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.05 _diffrn_reflns_theta_max 27.10 _reflns_number_total 2725 _reflns_number_gt 1982 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius COLLECT' _computing_cell_refinement 'Nonius DENZO' _computing_data_reduction 'Nonius DENZO' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0547P)^2^+0.1130P] 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 refall _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.025(4) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2725 _refine_ls_number_parameters 218 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0570 _refine_ls_R_factor_gt 0.0369 _refine_ls_wR_factor_ref 0.1003 _refine_ls_wR_factor_gt 0.0920 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_restrained_S_all 1.002 _refine_ls_shift/su_max 0.148 _refine_ls_shift/su_mean 0.018 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 0.31884(11) 0.29641(17) 0.40399(10) 0.0446(3) Uani 1 1 d . . . N2 N 0.26173(8) 0.21478(14) 0.47219(8) 0.0410(3) Uani 1 1 d . . . C3 C 0.33356(10) 0.14886(16) 0.56205(9) 0.0392(3) Uani 1 1 d . . . C3A C 0.44566(10) 0.18963(16) 0.55069(10) 0.0390(3) Uani 1 1 d . . . C4 C 0.54653(11) 0.15591(18) 0.61724(11) 0.0466(3) Uani 1 1 d . . . C5 C 0.63873(12) 0.2104(2) 0.58383(13) 0.0556(4) Uani 1 1 d . . . C6 C 0.62965(13) 0.2935(2) 0.48787(14) 0.0604(4) Uani 1 1 d . . . C7 C 0.52829(13) 0.3266(2) 0.42135(13) 0.0553(4) Uani 1 1 d . . . C7A C 0.43636(11) 0.27470(17) 0.45495(11) 0.0434(3) Uani 1 1 d . . . C1' C 0.09019(10) 0.27986(16) 0.52708(10) 0.0404(3) Uani 1 1 d . . . C2' C 0.14482(10) 0.20932(16) 0.45418(10) 0.0399(3) Uani 1 1 d . . . C3' C 0.08645(12) 0.12903(19) 0.36293(11) 0.0496(4) Uani 1 1 d . . . C4' C -0.02637(12) 0.1193(2) 0.34269(12) 0.0555(4) Uani 1 1 d . . . C5' C -0.08117(12) 0.1866(2) 0.41456(12) 0.0550(4) Uani 1 1 d . . . C6' C -0.02357(11) 0.26483(18) 0.50600(12) 0.0487(3) Uani 1 1 d . . . C7' C 0.14915(11) 0.37550(17) 0.62286(10) 0.0423(3) Uani 1 1 d . . . O1 O 0.27620(9) 0.36868(15) 0.32287(8) 0.0650(3) Uani 1 1 d . . . O2 O 0.30449(7) 0.07230(13) 0.63225(7) 0.0504(3) Uani 1 1 d . . . O3 O 0.23777(8) 0.44096(13) 0.63242(8) 0.0546(3) Uani 1 1 d . . . O4 O 0.09183(9) 0.38596(16) 0.69726(8) 0.0647(3) Uani 1 1 d . . . H4 H 0.5534(11) 0.0957(19) 0.6862(12) 0.055(4) Uiso 1 1 d . . . H5 H 0.7114(13) 0.191(2) 0.6292(13) 0.063(5) Uiso 1 1 d . . . H6 H 0.6959(13) 0.328(2) 0.4655(13) 0.066(5) Uiso 1 1 d . . . H7 H 0.5211(12) 0.384(2) 0.3526(13) 0.063(4) Uiso 1 1 d . . . H3' H 0.1269(12) 0.0797(19) 0.3161(12) 0.058(4) Uiso 1 1 d . . . H4' H -0.0683(11) 0.0641(18) 0.2773(12) 0.055(4) Uiso 1 1 d . . . H5' H -0.1607(14) 0.181(2) 0.3991(12) 0.065(5) Uiso 1 1 d . . . H6' H -0.0626(12) 0.3145(19) 0.5568(12) 0.056(4) Uiso 1 1 d . . . H4O H 0.1281(16) 0.454(3) 0.7533(16) 0.095(6) 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 0.0560(8) 0.0451(8) 0.0337(7) 0.0022(6) 0.0125(6) -0.0023(6) N2 0.0432(6) 0.0474(6) 0.0324(6) 0.0037(5) 0.0083(4) 0.0008(5) C3 0.0458(7) 0.0403(7) 0.0319(6) 0.0002(5) 0.0099(5) 0.0018(5) C3A 0.0438(7) 0.0379(7) 0.0367(6) -0.0055(5) 0.0122(5) 0.0001(5) C4 0.0474(8) 0.0488(8) 0.0439(8) -0.0048(6) 0.0106(6) 0.0016(6) C5 0.0431(8) 0.0595(10) 0.0642(10) -0.0099(8) 0.0126(7) -0.0010(7) C6 0.0541(9) 0.0591(10) 0.0755(11) -0.0067(8) 0.0306(8) -0.0073(7) C7 0.0622(9) 0.0539(9) 0.0569(9) 0.0035(7) 0.0282(8) -0.0036(7) C7A 0.0520(8) 0.0408(7) 0.0403(7) -0.0013(6) 0.0163(6) -0.0022(6) C1' 0.0441(7) 0.0378(7) 0.0378(7) 0.0022(5) 0.0062(5) -0.0019(5) C2' 0.0421(7) 0.0411(7) 0.0346(7) 0.0040(5) 0.0049(5) 0.0000(5) C3' 0.0553(8) 0.0522(9) 0.0388(7) -0.0046(6) 0.0052(6) 0.0029(7) C4' 0.0548(9) 0.0551(9) 0.0487(8) -0.0086(7) -0.0046(7) -0.0025(7) C5' 0.0434(8) 0.0559(9) 0.0607(9) -0.0033(7) 0.0012(7) -0.0022(7) C6' 0.0436(8) 0.0498(8) 0.0525(8) -0.0030(7) 0.0105(6) -0.0014(6) C7' 0.0452(7) 0.0425(7) 0.0393(7) -0.0007(6) 0.0095(6) -0.0015(6) O1 0.0706(7) 0.0770(8) 0.0442(6) 0.0210(5) 0.0066(5) -0.0046(6) O2 0.0495(5) 0.0612(6) 0.0411(5) 0.0142(5) 0.0118(4) -0.0004(4) O3 0.0494(6) 0.0610(6) 0.0534(6) -0.0121(5) 0.0120(4) -0.0134(5) O4 0.0619(6) 0.0883(9) 0.0491(6) -0.0235(6) 0.0231(5) -0.0223(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.2042(16) . ? C1 N2 1.4098(16) . ? C1 C7A 1.4789(19) . ? N2 C3 1.3955(16) . ? N2 C2' 1.4302(16) . ? C3 O2 1.2115(15) . ? C3 C3A 1.4802(18) . ? C3A C4 1.3817(19) . ? C3A C7A 1.3866(18) . ? C4 C5 1.390(2) . ? C5 C6 1.382(2) . ? C6 C7 1.385(2) . ? C7 C7A 1.3819(19) . ? C1' C6' 1.3936(19) . ? C1' C2' 1.3984(18) . ? C1' C7' 1.4914(18) . ? C2' C3' 1.3886(19) . ? C3' C4' 1.380(2) . ? C4' C5' 1.379(2) . ? C5' C6' 1.380(2) . ? C7' O3 1.2052(15) . ? C7' O4 1.3255(16) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 N2 124.79(12) . . ? O1 C1 C7A 129.81(13) . . ? N2 C1 C7A 105.39(11) . . ? C3 N2 C1 111.43(10) . . ? C3 N2 C2' 124.47(10) . . ? C1 N2 C2' 124.00(10) . . ? O2 C3 N2 124.02(12) . . ? O2 C3 C3A 129.51(12) . . ? N2 C3 C3A 106.47(10) . . ? C4 C3A C7A 121.68(13) . . ? C4 C3A C3 130.59(12) . . ? C7A C3A C3 107.73(11) . . ? C3A C4 C5 117.06(14) . . ? C6 C5 C4 121.33(15) . . ? C5 C6 C7 121.35(14) . . ? C7A C7 C6 117.51(15) . . ? C3A C7A C7 121.06(13) . . ? C3A C7A C1 108.93(11) . . ? C7 C7A C1 130.00(13) . . ? C6' C1' C2' 118.07(12) . . ? C6' C1' C7' 119.72(12) . . ? C2' C1' C7' 122.15(11) . . ? C3' C2' C1' 120.49(12) . . ? C3' C2' N2 118.23(12) . . ? C1' C2' N2 121.27(11) . . ? C2' C3' C4' 120.30(13) . . ? C5' C4' C3' 119.79(14) . . ? C4' C5' C6' 120.20(14) . . ? C5' C6' C1' 121.12(14) . . ? O3 C7' O4 122.53(12) . . ? O3 C7' C1' 124.93(12) . . ? O4 C7' C1' 112.51(11) . . ? 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 O1 C1 N2 C3 -177.45(13) . . . . ? C7A C1 N2 C3 1.66(14) . . . . ? O1 C1 N2 C2' -0.9(2) . . . . ? C7A C1 N2 C2' 178.25(11) . . . . ? C1 N2 C3 O2 -179.64(12) . . . . ? C2' N2 C3 O2 3.8(2) . . . . ? C1 N2 C3 C3A -0.51(14) . . . . ? C2' N2 C3 C3A -177.08(11) . . . . ? O2 C3 C3A C4 -1.8(2) . . . . ? N2 C3 C3A C4 179.13(13) . . . . ? O2 C3 C3A C7A 178.12(13) . . . . ? N2 C3 C3A C7A -0.94(14) . . . . ? C7A C3A C4 C5 -0.3(2) . . . . ? C3 C3A C4 C5 179.65(13) . . . . ? C3A C4 C5 C6 -0.5(2) . . . . ? C4 C5 C6 C7 0.4(2) . . . . ? C5 C6 C7 C7A 0.6(2) . . . . ? C4 C3A C7A C7 1.2(2) . . . . ? C3 C3A C7A C7 -178.73(13) . . . . ? C4 C3A C7A C1 -178.10(12) . . . . ? C3 C3A C7A C1 1.96(14) . . . . ? C6 C7 C7A C3A -1.3(2) . . . . ? C6 C7 C7A C1 177.83(14) . . . . ? O1 C1 C7A C3A 176.81(14) . . . . ? N2 C1 C7A C3A -2.24(14) . . . . ? O1 C1 C7A C7 -2.4(3) . . . . ? N2 C1 C7A C7 178.53(14) . . . . ? C6' C1' C2' C3' 0.90(19) . . . . ? C7' C1' C2' C3' -176.50(12) . . . . ? C6' C1' C2' N2 -177.90(12) . . . . ? C7' C1' C2' N2 4.70(18) . . . . ? C3 N2 C2' C3' -121.59(14) . . . . ? C1 N2 C2' C3' 62.26(17) . . . . ? C3 N2 C2' C1' 57.24(17) . . . . ? C1 N2 C2' C1' -118.91(14) . . . . ? C1' C2' C3' C4' 0.6(2) . . . . ? N2 C2' C3' C4' 179.41(13) . . . . ? C2' C3' C4' C5' -1.3(2) . . . . ? C3' C4' C5' C6' 0.6(2) . . . . ? C4' C5' C6' C1' 0.9(2) . . . . ? C2' C1' C6' C5' -1.7(2) . . . . ? C7' C1' C6' C5' 175.81(13) . . . . ? C6' C1' C7' O3 -155.86(14) . . . . ? C2' C1' C7' O3 21.5(2) . . . . ? C6' C1' C7' O4 22.31(17) . . . . ? C2' C1' C7' O4 -160.33(12) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.10 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.141 _refine_diff_density_min -0.134 _refine_diff_density_rms 0.028