#------------------------------------------------------------------------------ #$Date: 2014-07-12 07:06:18 +0300 (Sat, 12 Jul 2014) $ #$Revision: 120112 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/20/59/7205993.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_7205993 loop_ _publ_author_name 'Thompson, Laura J.' 'Voguri, Raja S.' 'Male, Louise' 'Tremayne, Maryjane' _publ_section_title ; The crystal structures and melting point properties of isonicotinamide cocrystals with alkanediacids HO2C(CH2)n−2CO2H n = 7--9 ; _journal_issue 12 _journal_name_full CrystEngComm _journal_page_first 4188 _journal_volume 13 _journal_year 2011 _chemical_formula_moiety 'C7 H12 O4, C6 H6 N2 O' _chemical_formula_sum 'C13 H18 N2 O5' _chemical_formula_weight 282.29 _chemical_name_systematic ; Isonicotinamide:pimelic acid ; _space_group_IT_number 13 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yc' _symmetry_space_group_name_H-M 'P 1 2/c 1' _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 93.873(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 8.2223(5) _cell_length_b 5.1437(3) _cell_length_c 33.389(2) _cell_measurement_reflns_used 15181 _cell_measurement_temperature 120(2) _cell_measurement_theta_max 27.48 _cell_measurement_theta_min 2.91 _cell_volume 1408.90(15) _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX (Farrugia, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _diffrn_ambient_temperature 120(2) _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_device_type 'Bruker-Nonius Roper CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0742 _diffrn_reflns_av_sigmaI/netI 0.0627 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 39 _diffrn_reflns_limit_l_min -39 _diffrn_reflns_number 13904 _diffrn_reflns_theta_full 25.02 _diffrn_reflns_theta_max 25.02 _diffrn_reflns_theta_min 3.37 _exptl_absorpt_coefficient_mu 0.103 _exptl_absorpt_correction_T_max 0.9949 _exptl_absorpt_correction_T_min 0.9898 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _exptl_crystal_colour Colourless _exptl_crystal_density_diffrn 1.331 _exptl_crystal_density_method 'not measured' _exptl_crystal_description Fragment _exptl_crystal_F_000 600 _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.311 _refine_diff_density_min -0.305 _refine_diff_density_rms 0.101 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 183 _refine_ls_number_reflns 2480 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.077 _refine_ls_R_factor_all 0.0901 _refine_ls_R_factor_gt 0.0557 _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^)+(0.0541P)^2^+0.5667P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1184 _refine_ls_wR_factor_ref 0.1337 _reflns_number_gt 1772 _reflns_number_total 2480 _reflns_threshold_expression >2\s(I) _[local]_cod_data_source_file c1ce05160a.txt _[local]_cod_data_source_block 2010src0399 _[local]_cod_cif_authors_sg_H-M 'P 2/c' _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. '_exptl_absorpt_correction_type' value 'Multi-scan' changed to 'multi-scan' 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 1555 2011-01-17 13:19:09Z saulius ; _cod_database_code 7205993 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' 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 C2 C 0.7724(3) 0.1102(5) 0.55838(7) 0.0281(6) Uani 1 1 d . . . H2 H 0.7571 0.2137 0.5814 0.034 Uiso 1 1 calc R . . C3 C 0.6946(3) 0.1839(5) 0.52187(7) 0.0265(6) Uani 1 1 d . . . H3 H 0.6278 0.3348 0.5202 0.032 Uiso 1 1 calc R . . C4 C 0.7155(3) 0.0353(4) 0.48809(6) 0.0219(5) Uani 1 1 d . . . C5 C 0.8129(3) -0.1838(5) 0.49244(7) 0.0275(6) Uani 1 1 d . . . H5 H 0.8289 -0.2923 0.4700 0.033 Uiso 1 1 calc R . . C6 C 0.8865(3) -0.2429(5) 0.52972(7) 0.0285(6) Uani 1 1 d . . . H6 H 0.9540 -0.3927 0.5322 0.034 Uiso 1 1 calc R . . C7 C 0.6307(3) 0.1164(5) 0.44875(7) 0.0223(6) Uani 1 1 d . . . N1 N 0.8674(2) -0.0994(4) 0.56251(5) 0.0245(5) Uani 1 1 d . . . N7 N 0.6493(2) -0.0290(4) 0.41674(5) 0.0292(5) Uani 1 1 d . . . H7A H 0.5996 0.0136 0.3935 0.035 Uiso 1 1 calc R . . H7B H 0.7113 -0.1685 0.4187 0.035 Uiso 1 1 calc R . . O7 O 0.5444(2) 0.3157(3) 0.44773(4) 0.0282(4) Uani 1 1 d . . . C8 C 0.4050(3) 0.3819(5) 0.34881(7) 0.0255(6) Uani 1 1 d . . . C9 C 0.3299(3) 0.5361(5) 0.31418(6) 0.0293(6) Uani 1 1 d . . . H9A H 0.4054 0.6784 0.3081 0.035 Uiso 1 1 calc R . . H9B H 0.2281 0.6169 0.3225 0.035 Uiso 1 1 calc R . . C10 C 0.2903(3) 0.3811(5) 0.27608(7) 0.0297(6) Uani 1 1 d . . . H10A H 0.1996 0.2601 0.2804 0.036 Uiso 1 1 calc R . . H10B H 0.3865 0.2759 0.2701 0.036 Uiso 1 1 calc R . . C11 C 0.2429(3) 0.5545(5) 0.24035(6) 0.0290(6) Uani 1 1 d . . . H11A H 0.3367 0.6671 0.2350 0.035 Uiso 1 1 calc R . . H11B H 0.1521 0.6689 0.2473 0.035 Uiso 1 1 calc R . . C12 C 0.1909(3) 0.4059(5) 0.20217(6) 0.0288(6) Uani 1 1 d . . . H12A H 0.2775 0.2805 0.1963 0.035 Uiso 1 1 calc R . . H12B H 0.0907 0.3060 0.2065 0.035 Uiso 1 1 calc R . . C13 C 0.1590(3) 0.5859(5) 0.16631(7) 0.0306(6) Uani 1 1 d . . . H13A H 0.0799 0.7201 0.1736 0.037 Uiso 1 1 calc R . . H13B H 0.2621 0.6761 0.1614 0.037 Uiso 1 1 calc R . . C14 C 0.0949(3) 0.4602(5) 0.12760(7) 0.0262(6) Uani 1 1 d . . . O8 O 0.4114(2) 0.5174(3) 0.38253(5) 0.0372(5) Uani 1 1 d . . . H8 H 0.4565 0.4280 0.4012 0.056 Uiso 1 1 calc R . . O9 O 0.4577(2) 0.1636(3) 0.34620(5) 0.0378(5) Uani 1 1 d . . . O14 O -0.0053(2) 0.2648(3) 0.13243(5) 0.0355(5) Uani 1 1 d . . . H14 H -0.0398 0.2077 0.1099 0.053 Uiso 1 1 calc R . . O15 O 0.1285(2) 0.5368(3) 0.09472(5) 0.0341(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 C2 0.0329(14) 0.0299(14) 0.0211(13) -0.0055(11) -0.0010(10) 0.0055(12) C3 0.0285(14) 0.0263(14) 0.0242(13) -0.0006(11) -0.0016(10) 0.0047(11) C4 0.0234(13) 0.0241(13) 0.0183(12) 0.0008(10) 0.0021(10) -0.0015(11) C5 0.0344(14) 0.0292(14) 0.0185(13) -0.0043(11) -0.0008(10) 0.0073(12) C6 0.0319(14) 0.0292(14) 0.0241(14) -0.0015(11) -0.0012(11) 0.0082(12) C7 0.0250(13) 0.0215(14) 0.0203(13) 0.0000(10) 0.0016(10) -0.0011(11) N1 0.0277(11) 0.0252(11) 0.0202(11) 0.0001(9) -0.0007(8) 0.0025(10) N7 0.0385(12) 0.0279(12) 0.0202(11) -0.0008(9) -0.0050(9) 0.0123(10) O7 0.0365(10) 0.0262(10) 0.0216(9) -0.0011(7) -0.0006(7) 0.0085(8) C8 0.0259(13) 0.0320(15) 0.0183(13) -0.0030(11) -0.0002(10) -0.0017(12) C9 0.0333(14) 0.0342(15) 0.0202(13) 0.0003(11) -0.0005(10) 0.0056(12) C10 0.0326(14) 0.0361(15) 0.0199(13) -0.0019(11) -0.0020(10) -0.0012(12) C11 0.0289(14) 0.0383(15) 0.0195(13) -0.0025(11) -0.0014(10) 0.0001(12) C12 0.0304(14) 0.0369(15) 0.0187(13) 0.0011(11) -0.0008(10) -0.0043(12) C13 0.0353(15) 0.0359(15) 0.0198(13) 0.0000(11) -0.0033(11) -0.0071(12) C14 0.0259(13) 0.0290(14) 0.0232(13) 0.0025(11) -0.0024(10) -0.0022(12) O8 0.0556(12) 0.0355(11) 0.0192(9) -0.0023(8) -0.0078(8) 0.0152(9) O9 0.0564(12) 0.0321(11) 0.0237(10) -0.0050(8) -0.0066(8) 0.0136(9) O14 0.0426(11) 0.0453(12) 0.0179(9) 0.0026(8) -0.0034(8) -0.0197(9) O15 0.0447(11) 0.0389(11) 0.0182(9) 0.0039(8) -0.0012(8) -0.0127(9) 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 N1 C2 C3 122.9(2) . . ? N1 C2 H2 118.6 . . ? C3 C2 H2 118.6 . . ? C4 C3 C2 119.3(2) . . ? C4 C3 H3 120.4 . . ? C2 C3 H3 120.4 . . ? C3 C4 C5 117.9(2) . . ? C3 C4 C7 118.9(2) . . ? C5 C4 C7 123.2(2) . . ? C6 C5 C4 119.3(2) . . ? C6 C5 H5 120.4 . . ? C4 C5 H5 120.4 . . ? N1 C6 C5 123.2(2) . . ? N1 C6 H6 118.4 . . ? C5 C6 H6 118.4 . . ? O7 C7 N7 122.7(2) . . ? O7 C7 C4 118.8(2) . . ? N7 C7 C4 118.5(2) . . ? C2 N1 C6 117.5(2) . . ? C7 N7 H7A 120.0 . . ? C7 N7 H7B 120.0 . . ? H7A N7 H7B 120.0 . . ? O9 C8 O8 123.8(2) . . ? O9 C8 C9 124.5(2) . . ? O8 C8 C9 111.6(2) . . ? C8 C9 C10 114.9(2) . . ? C8 C9 H9A 108.5 . . ? C10 C9 H9A 108.5 . . ? C8 C9 H9B 108.5 . . ? C10 C9 H9B 108.5 . . ? H9A C9 H9B 107.5 . . ? C9 C10 C11 112.2(2) . . ? C9 C10 H10A 109.2 . . ? C11 C10 H10A 109.2 . . ? C9 C10 H10B 109.2 . . ? C11 C10 H10B 109.2 . . ? H10A C10 H10B 107.9 . . ? C10 C11 C12 113.9(2) . . ? C10 C11 H11A 108.8 . . ? C12 C11 H11A 108.8 . . ? C10 C11 H11B 108.8 . . ? C12 C11 H11B 108.8 . . ? H11A C11 H11B 107.7 . . ? C13 C12 C11 112.1(2) . . ? C13 C12 H12A 109.2 . . ? C11 C12 H12A 109.2 . . ? C13 C12 H12B 109.2 . . ? C11 C12 H12B 109.2 . . ? H12A C12 H12B 107.9 . . ? C14 C13 C12 116.4(2) . . ? C14 C13 H13A 108.2 . . ? C12 C13 H13A 108.2 . . ? C14 C13 H13B 108.2 . . ? C12 C13 H13B 108.2 . . ? H13A C13 H13B 107.3 . . ? O15 C14 O14 122.7(2) . . ? O15 C14 C13 123.2(2) . . ? O14 C14 C13 114.1(2) . . ? C8 O8 H8 109.5 . . ? C14 O14 H14 109.5 . . ? 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 C2 N1 1.333(3) . ? C2 C3 1.390(3) . ? C2 H2 0.9500 . ? C3 C4 1.383(3) . ? C3 H3 0.9500 . ? C4 C5 1.385(3) . ? C4 C7 1.504(3) . ? C5 C6 1.380(3) . ? C5 H5 0.9500 . ? C6 N1 1.338(3) . ? C6 H6 0.9500 . ? C7 O7 1.246(3) . ? C7 N7 1.322(3) . ? N7 H7A 0.8800 . ? N7 H7B 0.8800 . ? C8 O9 1.209(3) . ? C8 O8 1.322(3) . ? C8 C9 1.500(3) . ? C9 C10 1.518(3) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.520(3) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.522(3) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.522(3) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.508(3) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 O15 1.216(3) . ? C14 O14 1.316(3) . ? O8 H8 0.8400 . ? O14 H14 0.8400 . ? 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 H7A O9 0.88 2.05 2.917(2) 168.4 . N7 H7B O15 0.88 2.08 2.927(3) 162.2 2_645 O8 H8 O7 0.84 1.77 2.586(2) 164.9 . O14 H14 N1 0.84 1.80 2.634(2) 174.4 4_455 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 N1 C2 C3 C4 0.0(4) . . . . ? C2 C3 C4 C5 0.6(3) . . . . ? C2 C3 C4 C7 179.9(2) . . . . ? C3 C4 C5 C6 -0.9(3) . . . . ? C7 C4 C5 C6 179.8(2) . . . . ? C4 C5 C6 N1 0.7(4) . . . . ? C3 C4 C7 O7 0.2(3) . . . . ? C5 C4 C7 O7 179.5(2) . . . . ? C3 C4 C7 N7 -178.9(2) . . . . ? C5 C4 C7 N7 0.3(3) . . . . ? C3 C2 N1 C6 -0.3(4) . . . . ? C5 C6 N1 C2 0.0(4) . . . . ? O9 C8 C9 C10 12.4(4) . . . . ? O8 C8 C9 C10 -169.6(2) . . . . ? C8 C9 C10 C11 -169.9(2) . . . . ? C9 C10 C11 C12 -176.0(2) . . . . ? C10 C11 C12 C13 -174.9(2) . . . . ? C11 C12 C13 C14 -175.6(2) . . . . ? C12 C13 C14 O15 -146.7(2) . . . . ? C12 C13 C14 O14 35.4(3) . . . . ? _journal_paper_doi 10.1039/c1ce05160a