#------------------------------------------------------------------------------ #$Date: 2016-03-24 03:10:49 +0200 (Thu, 24 Mar 2016) $ #$Revision: 179617 $ #$URL: file:///home/coder/svn-repositories/cod/cif/4/50/81/4508142.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_4508142 loop_ _publ_author_name 'Lemmerer, Andreas' 'Adsmond, Daniel A.' 'Esterhuysen, Catharine' 'Bernstein, Joel' _publ_section_title ; Polymorphic Co-crystals from Polymorphic Co-crystal Formers: Competition between Carboxylic Acid...Pyridine and Phenol...Pyridine Hydrogen Bonds ; _journal_issue 9 _journal_name_full 'Crystal Growth & Design' _journal_page_first 3935 _journal_paper_doi 10.1021/cg4006357 _journal_volume 13 _journal_year 2013 _chemical_absolute_configuration unk _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 ; (nicotinamide).(pimelic acid) Form II ; _space_group_IT_number 33 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2c -2n' _symmetry_space_group_name_H-M 'P n a 21' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_creation_date 2009-03-11T11:15:53-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 8.838(3) _cell_length_b 31.514(8) _cell_length_c 5.252(2) _cell_measurement_reflns_used 781 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 25.18 _cell_measurement_theta_min 2.33 _cell_volume 1462.8(8) _computing_cell_refinement 'Bruker SAINT+, Bruker (1999)' _computing_data_collection 'Bruker SMART, Bruker (1998)' _computing_data_reduction 'Bruker SAINT+' _computing_molecular_graphics ; Ortep-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999) ; _computing_publication_material ; WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2009) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_device_type 'Bruker SMART 1K 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 0.0998 _diffrn_reflns_av_unetI/netI 0.1082 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 38 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_number 7309 _diffrn_reflns_theta_full 25.49 _diffrn_reflns_theta_max 25.49 _diffrn_reflns_theta_min 2.39 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.099 _exptl_absorpt_correction_T_max 0.996 _exptl_absorpt_correction_T_min 0.9514 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.282 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 600 _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.04 _refine_diff_density_max 0.467 _refine_diff_density_min -0.403 _refine_diff_density_rms 0.06 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.02 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 183 _refine_ls_number_reflns 1525 _refine_ls_number_restraints 97 _refine_ls_restrained_S_all 1.051 _refine_ls_R_factor_all 0.1857 _refine_ls_R_factor_gt 0.0909 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1530P)^2^+1.2057P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2345 _refine_ls_wR_factor_ref 0.3072 _reflns_number_gt 725 _reflns_number_total 1525 _reflns_threshold_expression >2sigma(I) _cod_data_source_file cg4006357_si_002.cif _cod_data_source_block 6(II) _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26. Automatic conversion script Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius ; _cod_original_cell_volume 1462.7(8) _cod_original_sg_symbol_H-M Pna2(1) _cod_database_code 4508142 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, 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 C1 C 0.6090(16) 0.3726(4) 0.151(3) 0.101(4) Uani 1 1 d DU C2 C 0.6233(18) 0.4045(4) -0.061(3) 0.127(4) Uani 1 1 d DU H2A H 0.6862 0.3928 -0.1956 0.153 Uiso 1 1 calc R H2B H 0.5241 0.4103 -0.1322 0.153 Uiso 1 1 calc R C3 C 0.6880(19) 0.4426(4) 0.029(3) 0.141(5) Uani 1 1 d DU H3A H 0.7846 0.4362 0.1073 0.169 Uiso 1 1 calc R H3B H 0.6227 0.4544 0.1593 0.169 Uiso 1 1 calc R C4 C 0.7124(15) 0.4763(3) -0.180(3) 0.113(4) Uani 1 1 d DU H4A H 0.7753 0.4646 -0.3141 0.135 Uiso 1 1 calc R H4B H 0.6157 0.484 -0.2541 0.135 Uiso 1 1 calc R C5 C 0.7861(15) 0.5148(3) -0.074(3) 0.102(4) Uani 1 1 d DU H5A H 0.8806 0.5064 0.0052 0.122 Uiso 1 1 calc R H5B H 0.7216 0.5262 0.0593 0.122 Uiso 1 1 calc R C6 C 0.8190(13) 0.5499(3) -0.261(2) 0.080(3) Uani 1 1 d DU H6A H 0.8836 0.5389 -0.3953 0.096 Uiso 1 1 calc R H6B H 0.7248 0.559 -0.3391 0.096 Uiso 1 1 calc R C7 C 0.8942(12) 0.5875(3) -0.142(2) 0.075(3) Uani 1 1 d DU O1 O 0.4996(11) 0.3822(2) 0.316(2) 0.109(3) Uani 1 1 d U H1 H 0.4729 0.3607 0.3908 0.163 Uiso 1 1 calc R O2 O 0.6742(9) 0.3396(3) 0.1466(18) 0.098(3) Uani 1 1 d U O3 O 0.8939(9) 0.6206(2) -0.2904(16) 0.086(2) Uani 1 1 d U H3 H 0.944 0.6396 -0.2249 0.129 Uiso 1 1 calc R O4 O 0.9516(14) 0.5883(3) 0.0647(19) 0.135(4) Uani 1 1 d U C8 C 0.3938(10) 0.2418(3) 0.674(2) 0.057(2) Uani 1 1 d . C9 C 0.4485(11) 0.2759(3) 0.538(2) 0.066(3) Uani 1 1 d . H9 H 0.5123 0.2706 0.4009 0.079 Uiso 1 1 calc R C10 C 0.3226(11) 0.3236(4) 0.795(2) 0.073(3) Uani 1 1 d . H10 H 0.2984 0.3513 0.8386 0.088 Uiso 1 1 calc R C11 C 0.2636(11) 0.2914(3) 0.937(2) 0.074(3) Uani 1 1 d . H11 H 0.1989 0.2975 1.0717 0.089 Uiso 1 1 calc R C12 C 0.3004(11) 0.2497(3) 0.880(2) 0.069(3) Uani 1 1 d . H12 H 0.2631 0.2275 0.9786 0.083 Uiso 1 1 calc R C13 C 0.4407(11) 0.1983(3) 0.592(2) 0.065(3) Uani 1 1 d . N1 N 0.4042(10) 0.1658(3) 0.7444(18) 0.081(3) Uani 1 1 d . H1S H 0.4303 0.1404 0.7039 0.121 Uiso 1 1 calc R H1A H 0.3546 0.1704 0.8827 0.121 Uiso 1 1 calc R N2 N 0.4138(9) 0.3169(2) 0.5949(17) 0.066(2) Uani 1 1 d . O5 O 0.5120(8) 0.1930(2) 0.3914(15) 0.078(2) 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 C1 0.122(9) 0.084(5) 0.095(9) 0.022(6) 0.043(7) 0.011(5) C2 0.175(11) 0.088(6) 0.119(9) 0.029(6) 0.039(8) -0.019(7) C3 0.179(10) 0.102(7) 0.141(11) 0.022(7) 0.035(10) -0.042(8) C4 0.133(9) 0.074(6) 0.131(10) 0.012(5) 0.013(9) -0.026(6) C5 0.137(8) 0.065(5) 0.103(8) 0.018(5) -0.004(8) -0.010(5) C6 0.101(7) 0.059(4) 0.079(6) 0.008(4) -0.013(6) -0.008(5) C7 0.091(6) 0.060(4) 0.073(6) 0.011(4) -0.015(6) -0.005(5) O1 0.141(7) 0.068(5) 0.118(8) 0.025(5) 0.057(6) 0.034(5) O2 0.107(5) 0.090(5) 0.098(6) 0.013(5) 0.044(5) 0.017(4) O3 0.115(6) 0.062(4) 0.081(5) 0.015(4) -0.031(5) -0.020(4) O4 0.227(11) 0.075(5) 0.102(7) 0.020(5) -0.076(7) -0.029(6) C8 0.054(5) 0.068(6) 0.050(5) -0.007(5) 0.015(5) 0.006(4) C9 0.066(6) 0.069(6) 0.062(6) 0.007(5) 0.019(5) 0.003(5) C10 0.082(7) 0.068(6) 0.071(7) -0.014(6) 0.028(7) 0.001(6) C11 0.077(7) 0.076(6) 0.069(7) -0.004(6) 0.028(7) 0.015(6) C12 0.068(6) 0.078(7) 0.063(7) 0.002(6) 0.020(6) -0.001(5) C13 0.062(6) 0.077(6) 0.057(6) 0.002(6) 0.015(6) 0.003(5) N1 0.111(7) 0.065(5) 0.067(6) 0.012(5) 0.042(5) 0.008(5) N2 0.074(5) 0.057(5) 0.067(6) -0.003(4) 0.011(5) 0.007(4) O5 0.096(5) 0.066(4) 0.074(5) 0.007(4) 0.038(5) 0.012(3) 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 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 -1 0 0.02 0 1 0 0.02 -1 0 0 0.18 1 0 0 0.18 0 0 -1 0.2 0 0 1 0.2 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle O2 C1 O1 124.4(11) O2 C1 C2 121.8(13) O1 C1 C2 112.9(11) C3 C2 C1 110.7(14) C3 C2 H2A 109.5 C1 C2 H2A 109.5 C3 C2 H2B 109.5 C1 C2 H2B 109.5 H2A C2 H2B 108.1 C2 C3 C4 113.9(14) C2 C3 H3A 108.8 C4 C3 H3A 108.8 C2 C3 H3B 108.8 C4 C3 H3B 108.8 H3A C3 H3B 107.7 C5 C4 C3 110.9(12) C5 C4 H4A 109.5 C3 C4 H4A 109.5 C5 C4 H4B 109.5 C3 C4 H4B 109.5 H4A C4 H4B 108 C4 C5 C6 115.9(12) C4 C5 H5A 108.3 C6 C5 H5A 108.3 C4 C5 H5B 108.3 C6 C5 H5B 108.3 H5A C5 H5B 107.4 C7 C6 C5 113.1(10) C7 C6 H6A 108.9 C5 C6 H6A 108.9 C7 C6 H6B 108.9 C5 C6 H6B 108.9 H6A C6 H6B 107.8 O4 C7 O3 121.6(10) O4 C7 C6 125.8(10) O3 C7 C6 112.7(9) C1 O1 H1 109.5 C7 O3 H3 109.5 C9 C8 C12 118.3(9) C9 C8 C13 118.0(8) C12 C8 C13 123.7(9) N2 C9 C8 123.3(9) N2 C9 H9 118.4 C8 C9 H9 118.4 N2 C10 C11 123.0(10) N2 C10 H10 118.5 C11 C10 H10 118.5 C10 C11 C12 119.9(10) C10 C11 H11 120.1 C12 C11 H11 120.1 C8 C12 C11 118.5(10) C8 C12 H12 120.7 C11 C12 H12 120.7 O5 C13 N1 121.7(9) O5 C13 C8 120.7(9) N1 C13 C8 117.6(9) C13 N1 H1A 120 C13 N1 H1S 120 H1A N1 H1S 120 C10 N2 C9 117.0(9) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C1 O2 1.187(13) C1 O1 1.331(14) C1 C2 1.508(14) C2 C3 1.412(14) C2 H2A 0.97 C2 H2B 0.97 C3 C4 1.543(14) C3 H3A 0.97 C3 H3B 0.97 C4 C5 1.485(13) C4 H4A 0.97 C4 H4B 0.97 C5 C6 1.509(12) C5 H5A 0.97 C5 H5B 0.97 C6 C7 1.494(12) C6 H6A 0.97 C6 H6B 0.97 C7 O4 1.200(13) C7 O3 1.303(12) O1 H1 0.82 O3 H3 0.82 C8 C9 1.377(13) C8 C12 1.385(13) C8 C13 1.494(13) C9 N2 1.363(12) C9 H9 0.93 C10 N2 1.341(13) C10 C11 1.361(15) C10 H10 0.93 C11 C12 1.388(14) C11 H11 0.93 C12 H12 0.93 C13 O5 1.240(12) C13 N1 1.339(13) N1 H1A 0.86 N1 H1S 0.86 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 O1 H1 N2 0.82 1.82 2.637(11) 173 . O3 H3 O5 0.82 1.83 2.607(10) 158 4_654 N1 H1S O4 0.86 2.08 2.912(12) 163 4_645 N1 H1A O2 0.86 2.14 2.936(11) 155 3_456 C11 H11 O5 0.93 2.37 3.299(13) 173 3_456 C12 H12 O2 0.93 2.42 3.335(13) 167 3_456 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 O2 C1 C2 C3 -117.6(17) O1 C1 C2 C3 72.8(18) C1 C2 C3 C4 177.7(14) C2 C3 C4 C5 -177.8(13) C3 C4 C5 C6 178.8(13) C4 C5 C6 C7 -179.5(11) C5 C6 C7 O4 14.2(19) C5 C6 C7 O3 -166.6(11) C12 C8 C9 N2 -0.8(14) C13 C8 C9 N2 -179.9(10) N2 C10 C11 C12 1.5(18) C9 C8 C12 C11 1.4(14) C13 C8 C12 C11 -179.5(11) C10 C11 C12 C8 -1.8(16) C9 C8 C13 O5 -8.2(15) C12 C8 C13 O5 172.8(10) C9 C8 C13 N1 171.1(10) C12 C8 C13 N1 -7.9(15) C11 C10 N2 C9 -0.8(16) C8 C9 N2 C10 0.5(14)