#------------------------------------------------------------------------------ #$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: svn://www.crystallography.net/cod/cif/2/2203428.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2203428 loop_ _publ_author_name 'Rabile, M. Mohamed' 'Huang, Huan' 'Ghosh, Dipesh' 'Powell, Doug R.' 'Van Horn, J. David' _publ_section_title ; 2,2'-(Propane-1,3-diimino)dibenzoic acid ; _journal_issue 4 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o494 _journal_page_last o496 _journal_volume 60 _journal_year 2004 _chemical_formula_iupac 'C17 H18 N2 O4' _chemical_formula_moiety 'C17 H18 N2 O4' _chemical_formula_sum 'C17 H18 N2 O4' _chemical_formula_weight 314.33 _chemical_melting_point 200.5 _chemical_name_common 1,3-Bis(2'-carboxyphenylamine)propane _chemical_name_systematic '2,2'-(Propane-1,3-diimino)dibenzoic acid' _space_group_IT_number 56 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall '-P 2ab 2ac' _symmetry_space_group_name_H-M 'P c c n' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 11.9318(18) _cell_length_b 14.152(2) _cell_length_c 9.0323(14) _cell_measurement_reflns_used 4874 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 26.00 _cell_measurement_theta_min 2.23 _cell_volume 1525.2(4) _computing_cell_refinement SMART _computing_data_collection 'SMART (Bruker, 1998)' _computing_data_reduction 'SAINT (Bruker, 1998)' _computing_molecular_graphics 'SHELXTL (Bruker, 1998)' _computing_publication_material SHELXTL _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _diffrn_ambient_temperature 100(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Bruker Apex CCD area-detector' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0212 _diffrn_reflns_av_sigmaI/netI 0.0170 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 8887 _diffrn_reflns_theta_full 25.99 _diffrn_reflns_theta_max 25.99 _diffrn_reflns_theta_min 2.23 _diffrn_standards_decay_% 0.08 _diffrn_standards_interval_count 'the first 50 frames were repeated at the end of data collection' _diffrn_standards_number 175 _exptl_absorpt_coefficient_mu 0.099 _exptl_absorpt_correction_T_max 0.9844 _exptl_absorpt_correction_T_min 0.9542 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 2000)' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.369 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 664 _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.16 _refine_diff_density_max 0.346 _refine_diff_density_min -0.323 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 105 _refine_ls_number_reflns 1504 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.016 _refine_ls_R_factor_all 0.0443 _refine_ls_R_factor_gt 0.0416 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0710P)^2^+0.67P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1151 _refine_ls_wR_factor_ref 0.1179 _reflns_number_gt 1382 _reflns_number_total 1504 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file fl6087.cif _[local]_cod_data_source_block I _cod_database_code 2203428 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z' '-x, y+1/2, -z+1/2' 'x+1/2, -y, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z' 'x, -y-1/2, z-1/2' '-x-1/2, y, z-1/2' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_type_symbol O1 -0.00109(8) 0.60117(6) 0.87857(11) 0.0299(3) Uani d . 1 O H1 -0.0243 0.5726 0.9691 0.036 Uiso d R 1 H C2 0.04850(11) 0.53332(9) 0.80214(15) 0.0238(3) Uani d . 1 C O3 0.05625(8) 0.45211(6) 0.85268(10) 0.0265(3) Uani d . 1 O C4 0.09160(11) 0.56161(9) 0.65702(14) 0.0236(3) Uani d . 1 C C5 0.07945(12) 0.65648(9) 0.61282(16) 0.0276(3) Uani d . 1 C H5 0.0457 0.7004 0.6787 0.033 Uiso calc R 1 H C6 0.11548(13) 0.68686(10) 0.47600(17) 0.0327(4) Uani d . 1 C H6 0.1082 0.7513 0.4482 0.039 Uiso calc R 1 H C7 0.16278(12) 0.62161(10) 0.37911(16) 0.0312(4) Uani d . 1 C H7 0.1857 0.6418 0.2835 0.037 Uiso calc R 1 H C8 0.17698(11) 0.52867(10) 0.41875(16) 0.0268(3) Uani d . 1 C H8 0.2090 0.4856 0.3501 0.032 Uiso calc R 1 H C9 0.14443(11) 0.49629(9) 0.56085(14) 0.0230(3) Uani d . 1 C N10 0.16511(10) 0.40530(7) 0.60348(13) 0.0260(3) Uani d . 1 N H10 0.1497 0.3897 0.6956 0.031 Uiso calc R 1 H C11 0.21071(12) 0.33265(8) 0.50771(14) 0.0248(3) Uani d . 1 C H11A 0.2744 0.3585 0.4503 0.030 Uiso calc R 1 H H11B 0.1526 0.3112 0.4371 0.030 Uiso calc R 1 H C12 0.2500 0.2500 0.6012(2) 0.0258(4) Uani d S 1 C H12A 0.3123 0.2710 0.6658 0.031 Uiso calc PR 0.50 H H12B 0.1877 0.2290 0.6658 0.031 Uiso calc PR 0.50 H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O1 0.0415(6) 0.0204(5) 0.0278(5) 0.0034(4) 0.0075(4) -0.0009(4) C2 0.0259(7) 0.0202(6) 0.0253(7) -0.0001(5) -0.0027(5) -0.0038(5) O3 0.0362(6) 0.0190(5) 0.0242(5) 0.0019(4) 0.0032(4) -0.0005(4) C4 0.0247(7) 0.0212(7) 0.0248(7) -0.0015(5) -0.0025(5) -0.0002(5) C5 0.0291(7) 0.0216(6) 0.0322(7) 0.0034(5) -0.0006(5) -0.0004(5) C6 0.0363(8) 0.0231(7) 0.0387(8) 0.0044(6) 0.0023(6) 0.0082(6) C7 0.0327(8) 0.0307(8) 0.0302(7) 0.0027(6) 0.0040(6) 0.0088(6) C8 0.0277(7) 0.0248(7) 0.0278(7) 0.0027(5) 0.0017(5) 0.0023(5) C9 0.0240(6) 0.0197(6) 0.0252(7) -0.0008(5) -0.0024(5) 0.0013(5) N10 0.0373(7) 0.0197(6) 0.0211(6) 0.0011(5) 0.0035(4) -0.0003(4) C11 0.0306(7) 0.0199(6) 0.0240(7) 0.0014(5) 0.0028(5) -0.0012(5) C12 0.0355(10) 0.0213(9) 0.0205(8) -0.0011(8) 0.000 0.000 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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle _geom_angle_publ_flag C2 O1 H1 . 105.7 no O3 C2 O1 . 120.90(10) y O3 C2 C4 . 123.80(10) y O1 C2 C4 . 115.20(10) y C5 C4 C9 . 119.60(10) y C5 C4 C2 . 118.60(10) y C9 C4 C2 . 121.80(10) y C6 C5 C4 . 121.33(13) no C6 C5 H5 . 119.3 no C4 C5 H5 . 119.3 no C5 C6 C7 . 118.92(12) no C5 C6 H6 . 120.5 no C7 C6 H6 . 120.5 no C8 C7 C6 . 121.43(13) no C8 C7 H7 . 119.3 no C6 C7 H7 . 119.3 no C7 C8 C9 . 120.79(13) no C7 C8 H8 . 119.6 no C9 C8 H8 . 119.6 no N10 C9 C4 . 121.50(10) y N10 C9 C8 . 120.70(10) y C4 C9 C8 . 117.80(10) y C9 N10 C11 . 124.60(10) y C9 N10 H10 . 117.7 no C11 N10 H10 . 117.7 no N10 C11 C12 . 109.30(10) yes N10 C11 H11A . 109.8 no C12 C11 H11A . 109.8 no N10 C11 H11B . 109.8 no C12 C11 H11B . 109.8 no H11A C11 H11B . 108.3 no C11 C12 C11 2 112.30(10) y C11 C12 H12A 2 109.1 no C11 C12 H12A . 109.1 no C11 C12 H12B 2 109.1 no C11 C12 H12B . 109.1 no H12A C12 H12B . 107.9 no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 C2 . 1.322(2) y O1 H1 . 0.9531 no C2 O3 . 1.240(2) y C2 C4 . 1.464(2) y C4 C5 . 1.408(2) no C4 C9 . 1.416(2) y C5 C6 . 1.377(2) no C5 H5 . 0.9500 no C6 C7 . 1.392(2) no C6 H6 . 0.9500 no C7 C8 . 1.3736(19) no C7 H7 . 0.9500 no C8 C9 . 1.4171(19) no C8 H8 . 0.9500 no C9 N10 . 1.366(2) y N10 C11 . 1.450(2) y N10 H10 . 0.8800 no C11 H11A . 0.9900 no C11 H11B . 0.9900 no C12 C11 2 1.5171(16) no C12 H12A . 0.9900 no C12 H12B . 0.9900 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag O1 H1 O3 5_567 0.95 1.69 2.6260(10) 166 yes N10 H10 O3 ? 0.88 2.01 2.6820(10) 132 yes 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_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag O3 C2 C4 C5 . -178.91(12) no O1 C2 C4 C5 . 1.33(18) no O3 C2 C4 C9 . 1.3(2) y O1 C2 C4 C9 . -178.50(10) y C9 C4 C5 C6 . 1.6(2) no C2 C4 C5 C6 . -178.19(13) no C4 C5 C6 C7 . 1.2(2) no C5 C6 C7 C8 . -1.9(2) no C6 C7 C8 C9 . -0.5(2) no C5 C4 C9 N10 . 175.26(12) no C2 C4 C9 N10 . -4.9(2) y C5 C4 C9 C8 . -3.82(19) no C2 C4 C9 C8 . 175.99(12) no C7 C8 C9 N10 . -175.81(13) no C7 C8 C9 C4 . 3.3(2) no C4 C9 N10 C11 . 175.00(10) y C8 C9 N10 C11 . -6.0(2) no C9 N10 C11 C12 . 165.34(11) no N10 C11 C12 C11 2 175.00(10) y