#------------------------------------------------------------------------------ #$Date: 2012-02-26 23:34:47 +0200 (Sun, 26 Feb 2012) $ #$Revision: 35909 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/20/17/7201770.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7201770 loop_ _publ_author_name 'Goswami, Shyamaprosad' 'Jana, Subrata' 'Fun, Hoong-Kun' _publ_section_title ; Recognition of dicarboxylic acids by 3,3′-bipyridine amide based receptors and its supramolecular behavior in solid state ; _journal_issue 5 _journal_name_full CrystEngComm _journal_page_first 507 _journal_volume 10 _journal_year 2008 _chemical_formula_sum 'C13 H18 N2 O3' _chemical_formula_weight 250.29 _chemical_name_common ; Recognition of Dicarboxylic Acids by 3,3/-Bipyridine Amide Based Receptors and Its Supramolecular Behavior in the Solid State ; _chemical_name_systematic ; ? ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 98.753(2) _cell_angle_beta 103.129(1) _cell_angle_gamma 91.122(1) _cell_formula_units_Z 2 _cell_length_a 5.7920(4) _cell_length_b 9.9488(7) _cell_length_c 12.1657(8) _cell_measurement_reflns_used 1287 _cell_measurement_temperature 297(2) _cell_measurement_theta_max 30.09 _cell_measurement_theta_min 1.74 _cell_volume 673.69(8) _computing_cell_refinement APEX2 _computing_data_collection 'APEX2 (Bruker, 2005)' _computing_data_reduction 'SAINT (Bruker, 2005)' _computing_molecular_graphics SHELXTL _computing_publication_material ; SHELXTL and PLATON (Spek, 2003) ; _computing_structure_refinement SHELXTL _computing_structure_solution 'SHELXTL (Sheldrick, 1998)' _diffrn_ambient_temperature 297(2) _diffrn_detector_area_resol_mean 8.33 _diffrn_measured_fraction_theta_full 0.992 _diffrn_measured_fraction_theta_max 0.992 _diffrn_measurement_device_type ; Brucker SMART APEX2 CCD diffractometer ; _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0304 _diffrn_reflns_av_sigmaI/netI 0.0454 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 8512 _diffrn_reflns_theta_full 30.09 _diffrn_reflns_theta_max 30.09 _diffrn_reflns_theta_min 1.74 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_T_max 0.9917 _exptl_absorpt_correction_T_min 0.9440 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Bruker, 2005)' _exptl_crystal_colour Colourless _exptl_crystal_density_diffrn 1.234 _exptl_crystal_density_method 'not measured' _exptl_crystal_description Plate _exptl_crystal_F_000 268 _exptl_crystal_size_max 0.66 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.10 _refine_diff_density_max 0.161 _refine_diff_density_min -0.171 _refine_diff_density_rms 0.039 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 235 _refine_ls_number_reflns 3928 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.021 _refine_ls_R_factor_all 0.1151 _refine_ls_R_factor_gt 0.0580 _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^)+(0.0872P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1494 _refine_ls_wR_factor_ref 0.1851 _reflns_number_gt 2025 _reflns_number_total 3928 _reflns_threshold_expression 'I > 2\s(I)' _[local]_cod_data_source_file b715136e.txt _[local]_cod_data_source_block spg376am _[local]_cod_cif_authors_sg_H-M P-1 _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius ; _cod_database_code 7201770 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' 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 0.4474(3) 0.88921(14) 0.13736(14) 0.0574(4) Uani 1 1 d . . . N2 N 0.5263(3) 0.67634(14) 0.18144(13) 0.0541(4) Uani 1 1 d . . . C1 C 0.3018(3) 0.97833(18) 0.08904(17) 0.0580(5) Uani 1 1 d . . . C2 C 0.0753(3) 0.94707(16) 0.02319(14) 0.0477(4) Uani 1 1 d . . . C3 C 0.0008(4) 0.81034(19) 0.00673(18) 0.0617(5) Uani 1 1 d . . . C4 C 0.1442(4) 0.71590(19) 0.05389(17) 0.0617(5) Uani 1 1 d . . . C5 C 0.3691(3) 0.75954(16) 0.12119(14) 0.0485(4) Uani 1 1 d . . . C6 C 0.4989(3) 0.53798(17) 0.17717(16) 0.0510(4) Uani 1 1 d . . . C7 C 0.6736(3) 0.48102(18) 0.27104(19) 0.0592(5) Uani 1 1 d . . . C8 C 0.6027(6) 0.3305(3) 0.2616(4) 0.1073(12) Uani 1 1 d . . . C9 C 0.6580(6) 0.5574(3) 0.3885(2) 0.0844(8) Uani 1 1 d . . . C10 C 0.9262(4) 0.4964(3) 0.2562(3) 0.0792(7) Uani 1 1 d . . . O1 O 0.3465(3) 0.46750(13) 0.10614(13) 0.0714(5) Uani 1 1 d . . . O2 O 0.8518(3) 1.02538(14) 0.25766(14) 0.0769(5) Uani 1 1 d . . . C11 C 0.9936(3) 0.95726(18) 0.32578(16) 0.0531(5) Uani 1 1 d . . . C12 C 1.2136(4) 1.0386(2) 0.3951(2) 0.0610(5) Uani 1 1 d . . . C13 C 1.3937(3) 0.9567(2) 0.4628(2) 0.0605(5) Uani 1 1 d . . . O3 O 0.9489(3) 0.84059(14) 0.33226(15) 0.0839(5) Uani 1 1 d . . . H1 H 0.365(4) 1.071(2) 0.1055(17) 0.068(6) Uiso 1 1 d . . . H3 H -0.162(4) 0.778(2) -0.0362(19) 0.083(7) Uiso 1 1 d . . . H4 H 0.079(4) 0.622(2) 0.0467(18) 0.077(6) Uiso 1 1 d . . . H8A H 0.611(7) 0.282(4) 0.181(3) 0.147(15) Uiso 1 1 d . . . H8B H 0.432(7) 0.316(3) 0.269(3) 0.148(13) Uiso 1 1 d . . . H8C H 0.709(7) 0.304(3) 0.331(3) 0.140(12) Uiso 1 1 d . . . H9A H 0.491(7) 0.567(3) 0.395(3) 0.143(13) Uiso 1 1 d . . . H9B H 0.724(5) 0.655(3) 0.401(2) 0.101(8) Uiso 1 1 d . . . H9C H 0.761(5) 0.515(2) 0.447(2) 0.097(8) Uiso 1 1 d . . . H10A H 0.930(6) 0.452(4) 0.174(3) 0.148(13) Uiso 1 1 d . . . H10B H 1.017(5) 0.438(3) 0.306(2) 0.103(9) Uiso 1 1 d . . . H10C H 0.973(5) 0.595(3) 0.265(2) 0.105(9) Uiso 1 1 d . . . H12A H 1.273(5) 1.093(3) 0.345(2) 0.098(8) Uiso 1 1 d . . . H12B H 1.160(4) 1.114(2) 0.445(2) 0.089(7) Uiso 1 1 d . . . H13A H 1.323(4) 0.904(2) 0.5118(19) 0.079(7) Uiso 1 1 d . . . H13B H 1.444(4) 0.882(2) 0.414(2) 0.085(7) Uiso 1 1 d . . . H1N2 H 0.666(4) 0.728(2) 0.2327(19) 0.075(6) Uiso 1 1 d . . . H1O2 H 0.698(5) 0.964(3) 0.212(2) 0.111(9) 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 N1 0.0416(8) 0.0434(7) 0.0732(10) 0.0130(7) -0.0174(7) -0.0049(6) N2 0.0435(8) 0.0417(7) 0.0646(9) 0.0108(7) -0.0141(7) -0.0023(7) C1 0.0424(9) 0.0433(9) 0.0752(12) 0.0132(8) -0.0149(9) -0.0038(8) C2 0.0404(9) 0.0456(8) 0.0483(9) 0.0093(7) -0.0089(8) -0.0025(7) C3 0.0460(10) 0.0496(10) 0.0726(12) 0.0113(9) -0.0208(9) -0.0075(8) C4 0.0525(11) 0.0443(9) 0.0719(12) 0.0135(8) -0.0208(9) -0.0082(8) C5 0.0422(9) 0.0445(8) 0.0502(9) 0.0093(7) -0.0080(8) 0.0002(7) C6 0.0388(9) 0.0448(9) 0.0650(11) 0.0084(8) 0.0031(8) 0.0005(7) C7 0.0444(10) 0.0472(9) 0.0818(13) 0.0200(9) -0.0008(10) 0.0066(8) C8 0.081(2) 0.0559(13) 0.168(3) 0.0458(18) -0.024(2) -0.0015(13) C9 0.0844(19) 0.099(2) 0.0726(15) 0.0375(14) 0.0076(14) 0.0185(16) C10 0.0486(12) 0.0750(15) 0.110(2) 0.0173(15) 0.0085(13) 0.0146(12) O1 0.0586(8) 0.0468(7) 0.0905(10) 0.0048(7) -0.0152(8) -0.0072(6) O2 0.0525(8) 0.0551(8) 0.1020(11) 0.0179(7) -0.0283(8) -0.0033(7) C11 0.0394(9) 0.0469(9) 0.0617(11) 0.0040(8) -0.0081(8) 0.0011(8) C12 0.0453(10) 0.0496(10) 0.0739(13) 0.0064(10) -0.0127(10) -0.0034(9) C13 0.0401(10) 0.0527(10) 0.0744(13) 0.0058(10) -0.0127(10) -0.0005(9) O3 0.0675(10) 0.0546(8) 0.1046(12) 0.0222(7) -0.0359(8) -0.0129(7) 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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 N1 C1 118.28(15) . . ? C6 N2 C5 127.17(14) . . ? C6 N2 H1N2 120.4(12) . . ? C5 N2 H1N2 112.4(13) . . ? N1 C1 C2 125.42(16) . . ? N1 C1 H1 114.9(13) . . ? C2 C1 H1 119.6(13) . . ? C1 C2 C3 114.70(16) . . ? C1 C2 C2 121.64(19) . 2_575 ? C3 C2 C2 123.64(19) . 2_575 ? C4 C3 C2 121.76(17) . . ? C4 C3 H3 117.2(13) . . ? C2 C3 H3 121.0(13) . . ? C3 C4 C5 118.65(17) . . ? C3 C4 H4 119.1(13) . . ? C5 C4 H4 121.9(13) . . ? N1 C5 C4 121.17(16) . . ? N1 C5 N2 114.14(15) . . ? C4 C5 N2 124.62(15) . . ? O1 C6 N2 122.63(17) . . ? O1 C6 C7 122.83(16) . . ? N2 C6 C7 114.53(15) . . ? C10 C7 C8 109.7(2) . . ? C10 C7 C6 110.64(19) . . ? C8 C7 C6 107.72(19) . . ? C10 C7 C9 109.7(2) . . ? C8 C7 C9 109.7(3) . . ? C6 C7 C9 109.38(17) . . ? C7 C8 H8A 108(2) . . ? C7 C8 H8B 112(2) . . ? H8A C8 H8B 107(3) . . ? C7 C8 H8C 103.2(19) . . ? H8A C8 H8C 120(3) . . ? H8B C8 H8C 107(3) . . ? C7 C9 H9A 112(2) . . ? C7 C9 H9B 111.4(15) . . ? H9A C9 H9B 103(2) . . ? C7 C9 H9C 108.0(14) . . ? H9A C9 H9C 117(2) . . ? H9B C9 H9C 105(2) . . ? C7 C10 H10A 109(2) . . ? C7 C10 H10B 104.7(16) . . ? H10A C10 H10B 105(2) . . ? C7 C10 H10C 109.1(16) . . ? H10A C10 H10C 108(2) . . ? H10B C10 H10C 121(2) . . ? C11 O2 H1O2 110.7(14) . . ? O3 C11 O2 122.47(16) . . ? O3 C11 C12 123.79(17) . . ? O2 C11 C12 113.73(16) . . ? C11 C12 C13 114.31(16) . . ? C11 C12 H12A 107.9(15) . . ? C13 C12 H12A 116.1(16) . . ? C11 C12 H12B 106.7(15) . . ? C13 C12 H12B 111.9(14) . . ? H12A C12 H12B 98(2) . . ? C12 C13 C13 112.9(2) . 2_876 ? C12 C13 H13A 112.3(13) . . ? C13 C13 H13A 108.7(13) 2_876 . ? C12 C13 H13B 112.3(14) . . ? C13 C13 H13B 110.5(15) 2_876 . ? H13A C13 H13B 99.3(18) . . ? 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 C5 1.330(2) . ? N1 C1 1.344(2) . ? N2 C6 1.374(2) . ? N2 C5 1.401(2) . ? N2 H1N2 0.98(2) . ? C1 C2 1.375(2) . ? C1 H1 0.96(2) . ? C2 C3 1.390(3) . ? C2 C2 1.477(3) 2_575 ? C3 C4 1.371(3) . ? C3 H3 0.99(2) . ? C4 C5 1.393(2) . ? C4 H4 0.98(2) . ? C6 O1 1.209(2) . ? C6 C7 1.531(3) . ? C7 C10 1.521(3) . ? C7 C8 1.525(3) . ? C7 C9 1.536(3) . ? C8 H8A 1.03(4) . ? C8 H8B 1.02(4) . ? C8 H8C 1.00(4) . ? C9 H9A 0.99(4) . ? C9 H9B 1.02(3) . ? C9 H9C 0.97(3) . ? C10 H10A 1.04(4) . ? C10 H10B 0.97(3) . ? C10 H10C 1.00(3) . ? O2 C11 1.306(2) . ? O2 H1O2 1.06(3) . ? C11 O3 1.202(2) . ? C11 C12 1.501(2) . ? C12 C13 1.509(3) . ? C12 H12A 0.99(3) . ? C12 H12B 0.99(2) . ? C13 C13 1.514(4) 2_876 ? C13 H13A 1.00(2) . ? C13 H13B 0.97(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 C5 N1 C1 C2 0.0(3) . . . . ? N1 C1 C2 C3 -0.9(3) . . . . ? N1 C1 C2 C2 177.8(2) . . . 2_575 ? C1 C2 C3 C4 0.4(3) . . . . ? C2 C2 C3 C4 -178.2(2) 2_575 . . . ? C2 C3 C4 C5 0.8(3) . . . . ? C1 N1 C5 C4 1.4(3) . . . . ? C1 N1 C5 N2 -175.64(17) . . . . ? C3 C4 C5 N1 -1.8(3) . . . . ? C3 C4 C5 N2 174.90(18) . . . . ? C6 N2 C5 N1 -176.59(17) . . . . ? C6 N2 C5 C4 6.5(3) . . . . ? C5 N2 C6 O1 11.2(3) . . . . ? C5 N2 C6 C7 -167.60(17) . . . . ? O1 C6 C7 C10 115.2(2) . . . . ? N2 C6 C7 C10 -66.0(2) . . . . ? O1 C6 C7 C8 -4.7(3) . . . . ? N2 C6 C7 C8 174.1(2) . . . . ? O1 C6 C7 C9 -123.9(2) . . . . ? N2 C6 C7 C9 55.0(2) . . . . ? O3 C11 C12 C13 8.1(3) . . . . ? O2 C11 C12 C13 -172.54(19) . . . . ? C11 C12 C13 C13 -176.5(3) . . . 2_876 ?