# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_publication_text data_3nba_4pp #TrackingRef '19639_web_deposit_cif_file_0_ColinSeaton_1366368486.compiled_cifs.cif' _audit_update_record ; 2013-02-05 # Formatted by publCIF ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3-nitrobenzoic acid 4-phenylpyridine ; _chemical_name_common '3-nitrobenzoic acid 4-phenylpyridine' _chemical_melting_point ? _chemical_formula_moiety 'C7 H4.76 N O4, C11 H9.24 N' _chemical_formula_sum 'C18 H14 N2 O4' _chemical_formula_weight 322.31 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 P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 17.7951(6) _cell_length_b 6.9089(3) _cell_length_c 13.0784(5) _cell_angle_alpha 90.00 _cell_angle_beta 109.667(2) _cell_angle_gamma 90.00 _cell_volume 1514.12(10) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 9939 _cell_measurement_theta_min 2.43 _cell_measurement_theta_max 31.46 _exptl_crystal_description Plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.89 _exptl_crystal_size_mid 0.37 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.414 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 672 _exptl_absorpt_coefficient_mu 0.102 _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 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 31535 _diffrn_reflns_av_R_equivalents 0.0258 _diffrn_reflns_av_sigmaI/netI 0.0149 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.12 _diffrn_reflns_theta_max 32.13 _reflns_number_total 4557 _reflns_number_gt 3856 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0688P)^2^+0.3800P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4557 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0512 _refine_ls_R_factor_gt 0.0424 _refine_ls_wR_factor_ref 0.1255 _refine_ls_wR_factor_gt 0.1170 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 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 C1A C -0.15213(6) 0.73074(15) -0.06130(8) 0.0238(2) Uani 1 1 d . . . O1A O -0.15009(5) 0.83664(12) 0.02221(6) 0.03115(19) Uani 1 1 d . . . H1AO H -0.100(2) 0.843(4) 0.068(3) 0.053(9) Uiso 0.76(6) 1 d P . . O2A O -0.09331(5) 0.66217(14) -0.07574(7) 0.0369(2) Uani 1 1 d . . . C2A C -0.23428(5) 0.69577(14) -0.14064(8) 0.02124(19) Uani 1 1 d . . . C3A C -0.30161(5) 0.74374(14) -0.11451(8) 0.02130(19) Uani 1 1 d . . . H3A H -0.2969 0.8038 -0.0473 0.026 Uiso 1 1 calc R . . C4A C -0.37580(5) 0.70116(14) -0.18962(8) 0.02236(19) Uani 1 1 d . . . N1A N -0.44710(5) 0.74314(14) -0.16060(7) 0.0278(2) Uani 1 1 d . . . O3A O -0.43909(5) 0.83576(14) -0.07769(7) 0.0376(2) Uani 1 1 d . . . O4A O -0.51158(5) 0.68108(17) -0.22076(7) 0.0432(2) Uani 1 1 d . . . C5A C -0.38570(6) 0.61515(15) -0.28919(8) 0.0255(2) Uani 1 1 d . . . H5A H -0.4374 0.5869 -0.3386 0.031 Uiso 1 1 calc R . . C6A C -0.31792(6) 0.57148(15) -0.31466(8) 0.0272(2) Uani 1 1 d . . . H6A H -0.3230 0.5150 -0.3829 0.033 Uiso 1 1 calc R . . C7A C -0.24270(6) 0.61038(15) -0.24046(8) 0.0258(2) Uani 1 1 d . . . H7A H -0.1965 0.5785 -0.2580 0.031 Uiso 1 1 calc R . . N1B N -0.00747(5) 0.86593(13) 0.15723(7) 0.02584(19) Uani 1 1 d . . . H1BN H -0.056(4) 0.866(7) 0.111(5) 0.02(2) Uiso 0.24(6) 1 d P . . C1B C 0.00588(6) 0.89081(16) 0.26329(9) 0.0270(2) Uani 1 1 d . . . H1B H -0.0385 0.9105 0.2869 0.032 Uiso 1 1 calc R . . C2B C 0.08158(6) 0.88914(15) 0.34001(8) 0.0245(2) Uani 1 1 d . . . H2B H 0.0885 0.9068 0.4147 0.029 Uiso 1 1 calc R . . C3B C 0.14783(5) 0.86129(13) 0.30714(7) 0.02026(18) Uani 1 1 d . . . C4B C 0.13304(6) 0.83740(17) 0.19602(8) 0.0268(2) Uani 1 1 d . . . H4B H 0.1762 0.8196 0.1697 0.032 Uiso 1 1 calc R . . C5B C 0.05544(6) 0.83964(17) 0.12437(8) 0.0289(2) Uani 1 1 d . . . H5B H 0.0464 0.8219 0.0492 0.035 Uiso 1 1 calc R . . C6B C 0.23007(5) 0.85249(13) 0.38595(7) 0.02034(18) Uani 1 1 d . . . C7B C 0.24496(6) 0.76641(15) 0.48739(8) 0.0248(2) Uani 1 1 d . . . H7B H 0.2018 0.7172 0.5069 0.030 Uiso 1 1 calc R . . C8B C 0.32243(7) 0.75210(16) 0.56003(8) 0.0288(2) Uani 1 1 d . . . H8B H 0.3320 0.6931 0.6289 0.035 Uiso 1 1 calc R . . C9B C 0.38575(6) 0.82359(16) 0.53230(9) 0.0297(2) Uani 1 1 d . . . H9B H 0.4387 0.8129 0.5819 0.036 Uiso 1 1 calc R . . C10B C 0.37175(6) 0.91061(16) 0.43229(9) 0.0294(2) Uani 1 1 d . . . H10B H 0.4151 0.9608 0.4136 0.035 Uiso 1 1 calc R . . C11B C 0.29440(6) 0.92478(15) 0.35911(8) 0.0248(2) Uani 1 1 d . . . H11B H 0.2852 0.9840 0.2904 0.030 Uiso 1 1 calc R . . 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 C1A 0.0212(4) 0.0263(5) 0.0225(4) 0.0030(4) 0.0054(3) 0.0029(3) O1A 0.0215(3) 0.0394(4) 0.0280(4) -0.0084(3) 0.0023(3) 0.0047(3) O2A 0.0231(4) 0.0556(6) 0.0310(4) -0.0065(4) 0.0078(3) 0.0077(3) C2A 0.0206(4) 0.0203(4) 0.0210(4) 0.0026(3) 0.0045(3) 0.0022(3) C3A 0.0218(4) 0.0215(4) 0.0192(4) 0.0016(3) 0.0051(3) 0.0021(3) C4A 0.0202(4) 0.0229(4) 0.0228(4) 0.0036(4) 0.0056(3) 0.0012(3) N1A 0.0207(4) 0.0361(5) 0.0245(4) 0.0056(4) 0.0050(3) 0.0027(3) O3A 0.0286(4) 0.0519(5) 0.0325(4) -0.0058(4) 0.0107(3) 0.0059(3) O4A 0.0206(3) 0.0712(7) 0.0335(4) -0.0019(4) 0.0035(3) -0.0053(4) C5A 0.0254(4) 0.0245(5) 0.0225(4) 0.0015(4) 0.0024(3) -0.0015(4) C6A 0.0329(5) 0.0253(5) 0.0216(4) -0.0026(4) 0.0067(4) 0.0012(4) C7A 0.0269(4) 0.0255(5) 0.0253(5) 0.0006(4) 0.0093(4) 0.0038(4) N1B 0.0217(4) 0.0282(4) 0.0249(4) -0.0027(3) 0.0042(3) 0.0003(3) C1B 0.0223(4) 0.0314(5) 0.0287(5) -0.0060(4) 0.0101(4) -0.0016(4) C2B 0.0247(4) 0.0291(5) 0.0210(4) -0.0052(4) 0.0095(3) -0.0024(4) C3B 0.0214(4) 0.0204(4) 0.0188(4) 0.0000(3) 0.0065(3) -0.0005(3) C4B 0.0234(4) 0.0385(6) 0.0192(4) 0.0012(4) 0.0081(3) 0.0034(4) C5B 0.0265(5) 0.0396(6) 0.0190(4) 0.0002(4) 0.0056(4) 0.0036(4) C6B 0.0216(4) 0.0200(4) 0.0187(4) -0.0009(3) 0.0059(3) 0.0002(3) C7B 0.0295(5) 0.0257(5) 0.0189(4) -0.0003(4) 0.0079(4) -0.0033(4) C8B 0.0361(5) 0.0269(5) 0.0185(4) 0.0006(4) 0.0027(4) 0.0007(4) C9B 0.0264(5) 0.0278(5) 0.0280(5) -0.0037(4) 0.0002(4) 0.0028(4) C10B 0.0228(4) 0.0309(5) 0.0336(5) -0.0002(4) 0.0082(4) -0.0009(4) C11B 0.0242(4) 0.0260(5) 0.0242(4) 0.0041(4) 0.0082(4) 0.0004(4) _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 C1A O2A 1.2202(12) . ? C1A O1A 1.3049(12) . ? C1A C2A 1.5003(13) . ? O1A H1AO 0.89(4) . ? C2A C3A 1.3922(13) . ? C2A C7A 1.3940(14) . ? C3A C4A 1.3862(13) . ? C3A H3A 0.9500 . ? C4A C5A 1.3876(14) . ? C4A N1A 1.4704(12) . ? N1A O3A 1.2254(12) . ? N1A O4A 1.2295(12) . ? C5A C6A 1.3883(15) . ? C5A H5A 0.9500 . ? C6A C7A 1.3898(14) . ? C6A H6A 0.9500 . ? C7A H7A 0.9500 . ? N1B C1B 1.3372(14) . ? N1B C5B 1.3397(13) . ? N1B H1BN 0.87(8) . ? C1B C2B 1.3827(14) . ? C1B H1B 0.9500 . ? C2B C3B 1.3974(13) . ? C2B H2B 0.9500 . ? C3B C4B 1.3968(13) . ? C3B C6B 1.4807(13) . ? C4B C5B 1.3835(14) . ? C4B H4B 0.9500 . ? C5B H5B 0.9500 . ? C6B C7B 1.3955(13) . ? C6B C11B 1.3978(13) . ? C7B C8B 1.3897(14) . ? C7B H7B 0.9500 . ? C8B C9B 1.3859(16) . ? C8B H8B 0.9500 . ? C9B C10B 1.3837(16) . ? C9B H9B 0.9500 . ? C10B C11B 1.3905(14) . ? C10B H10B 0.9500 . ? C11B H11B 0.9500 . ? 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 O2A C1A O1A 124.30(9) . . ? O2A C1A C2A 121.15(9) . . ? O1A C1A C2A 114.54(8) . . ? C1A O1A H1AO 108.9(16) . . ? C3A C2A C7A 120.04(9) . . ? C3A C2A C1A 120.71(9) . . ? C7A C2A C1A 119.24(8) . . ? C4A C3A C2A 117.95(9) . . ? C4A C3A H3A 121.0 . . ? C2A C3A H3A 121.0 . . ? C3A C4A C5A 123.08(9) . . ? C3A C4A N1A 118.29(9) . . ? C5A C4A N1A 118.60(8) . . ? O3A N1A O4A 123.64(9) . . ? O3A N1A C4A 118.54(8) . . ? O4A N1A C4A 117.81(9) . . ? C4A C5A C6A 118.17(9) . . ? C4A C5A H5A 120.9 . . ? C6A C5A H5A 120.9 . . ? C5A C6A C7A 120.06(9) . . ? C5A C6A H6A 120.0 . . ? C7A C6A H6A 120.0 . . ? C6A C7A C2A 120.69(9) . . ? C6A C7A H7A 119.7 . . ? C2A C7A H7A 119.7 . . ? C1B N1B C5B 118.31(9) . . ? C1B N1B H1BN 120(3) . . ? C5B N1B H1BN 121(3) . . ? N1B C1B C2B 122.76(9) . . ? N1B C1B H1B 118.6 . . ? C2B C1B H1B 118.6 . . ? C1B C2B C3B 119.65(9) . . ? C1B C2B H2B 120.2 . . ? C3B C2B H2B 120.2 . . ? C4B C3B C2B 116.95(9) . . ? C4B C3B C6B 121.02(8) . . ? C2B C3B C6B 122.01(8) . . ? C5B C4B C3B 119.93(9) . . ? C5B C4B H4B 120.0 . . ? C3B C4B H4B 120.0 . . ? N1B C5B C4B 122.38(9) . . ? N1B C5B H5B 118.8 . . ? C4B C5B H5B 118.8 . . ? C7B C6B C11B 118.79(9) . . ? C7B C6B C3B 120.41(8) . . ? C11B C6B C3B 120.78(8) . . ? C8B C7B C6B 120.50(9) . . ? C8B C7B H7B 119.8 . . ? C6B C7B H7B 119.8 . . ? C9B C8B C7B 120.18(9) . . ? C9B C8B H8B 119.9 . . ? C7B C8B H8B 119.9 . . ? C10B C9B C8B 119.91(9) . . ? C10B C9B H9B 120.0 . . ? C8B C9B H9B 120.0 . . ? C9B C10B C11B 120.19(10) . . ? C9B C10B H10B 119.9 . . ? C11B C10B H10B 119.9 . . ? C10B C11B C6B 120.44(9) . . ? C10B C11B H11B 119.8 . . ? C6B C11B H11B 119.8 . . ? _diffrn_measured_fraction_theta_max 0.857 _diffrn_reflns_theta_full 29.50 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.408 _refine_diff_density_min -0.230 _refine_diff_density_rms 0.048 _database_code_depnum_ccdc_archive 'CCDC 923463' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_publication_text #END data_4aba_4pp #TrackingRef '19639_web_deposit_cif_file_0_ColinSeaton_1366368486.compiled_cifs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-aminobenzoic acid 4-phenylpyridine ; _chemical_name_common '4-aminobenzoic acid 4-phenylpyridine' _chemical_melting_point ? _chemical_formula_moiety 'C11 H9 N, C7 H7 N O2' _chemical_formula_sum 'C18 H16 N2 O2' _chemical_formula_weight 292.33 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 triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.1839(2) _cell_length_b 10.8800(3) _cell_length_c 19.2168(5) _cell_angle_alpha 73.5890(10) _cell_angle_beta 83.5580(10) _cell_angle_gamma 68.8970(10) _cell_volume 1531.19(7) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 9900 _cell_measurement_theta_min 2.21 _cell_measurement_theta_max 26.31 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.454 _exptl_crystal_size_mid 0.328 _exptl_crystal_size_min 0.245 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.268 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 616 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7085 _exptl_absorpt_correction_T_max 0.7460 _exptl_absorpt_process_details 'Bruker SAINT' _exptl_special_details ? _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 55932 _diffrn_reflns_av_R_equivalents 0.0443 _diffrn_reflns_av_sigmaI/netI 0.0358 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.60 _diffrn_reflns_theta_max 27.50 _reflns_number_total 6940 _reflns_number_gt 4744 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0518P)^2^+0.2902P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6940 _refine_ls_number_parameters 421 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0779 _refine_ls_R_factor_gt 0.0445 _refine_ls_wR_factor_ref 0.1143 _refine_ls_wR_factor_gt 0.0966 _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_restrained_S_all 1.020 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 N1A N 0.96460(17) 0.61971(15) 0.29317(8) 0.0409(3) Uani 1 1 d . . . O1A O 0.19633(13) 0.61808(12) 0.40313(6) 0.0455(3) Uani 1 1 d . . . O2A O 0.25793(14) 0.72483(12) 0.47460(6) 0.0441(3) Uani 1 1 d . . . C1A C 0.47865(17) 0.63787(14) 0.39404(7) 0.0283(3) Uani 1 1 d . . . C2A C 0.53215(18) 0.58364(14) 0.33453(7) 0.0308(3) Uani 1 1 d . . . H2A H 0.4561 0.5520 0.3161 0.037 Uiso 1 1 calc R . . C3A C 0.69261(19) 0.57475(15) 0.30169(8) 0.0328(3) Uani 1 1 d . . . H3A H 0.7252 0.5385 0.2606 0.039 Uiso 1 1 calc R . . C4A C 0.80845(17) 0.61869(14) 0.32819(8) 0.0295(3) Uani 1 1 d . . . C5A C 0.75861(18) 0.66691(15) 0.39039(8) 0.0327(3) Uani 1 1 d . . . H5A H 0.8375 0.6928 0.4109 0.039 Uiso 1 1 calc R . . C6A C 0.59663(17) 0.67711(14) 0.42208(8) 0.0314(3) Uani 1 1 d . . . H6A H 0.5645 0.7115 0.4638 0.038 Uiso 1 1 calc R . . C7A C 0.29898(18) 0.65781(15) 0.42387(8) 0.0322(3) Uani 1 1 d . . . N1B N 0.46308(17) 0.38828(16) 0.21080(8) 0.0406(3) Uani 1 1 d . . . O1B O -0.31622(13) 0.52228(11) 0.11056(6) 0.0451(3) Uani 1 1 d . . . O2B O -0.24377(14) 0.69358(12) 0.03645(6) 0.0457(3) Uani 1 1 d . . . C1B C -0.03027(17) 0.52624(14) 0.11770(7) 0.0276(3) Uani 1 1 d . . . C2B C 0.02077(18) 0.40946(14) 0.17512(7) 0.0294(3) Uani 1 1 d . . . H2B H -0.0586 0.3619 0.1938 0.035 Uiso 1 1 calc R . . C3B C 0.18434(18) 0.36123(14) 0.20560(7) 0.0305(3) Uani 1 1 d . . . H3B H 0.2162 0.2812 0.2448 0.037 Uiso 1 1 calc R . . C4B C 0.30346(17) 0.42964(14) 0.17906(7) 0.0285(3) Uani 1 1 d . . . C5B C 0.25411(17) 0.54515(14) 0.12043(8) 0.0317(3) Uani 1 1 d . . . H5B H 0.3340 0.5919 0.1011 0.038 Uiso 1 1 calc R . . C6B C 0.09069(17) 0.59214(14) 0.09034(8) 0.0310(3) Uani 1 1 d . . . H6B H 0.0598 0.6707 0.0503 0.037 Uiso 1 1 calc R . . C7B C -0.20917(18) 0.57920(15) 0.08824(8) 0.0316(3) Uani 1 1 d . . . N1C N 0.92942(15) 0.78222(14) 0.52639(7) 0.0395(3) Uani 1 1 d . . . C1C C 0.86588(19) 0.68344(16) 0.56017(8) 0.0381(4) Uani 1 1 d . . . H1C H 0.9350 0.5921 0.5602 0.046 Uiso 1 1 calc R . . C2C C 0.70505(19) 0.70686(15) 0.59510(8) 0.0341(3) Uani 1 1 d . . . H2C H 0.6655 0.6329 0.6181 0.041 Uiso 1 1 calc R . . C3C C 0.60108(18) 0.83933(14) 0.59652(7) 0.0301(3) Uani 1 1 d . . . C4C C 0.42586(18) 0.86991(15) 0.63234(7) 0.0319(3) Uani 1 1 d . . . C5C C 0.31806(19) 0.79680(16) 0.63042(8) 0.0366(3) Uani 1 1 d . . . H5C H 0.3576 0.7257 0.6065 0.044 Uiso 1 1 calc R . . C6C C 0.1537(2) 0.82689(18) 0.66314(8) 0.0448(4) Uani 1 1 d . . . H6C H 0.0813 0.7763 0.6616 0.054 Uiso 1 1 calc R . . C7C C 0.0948(2) 0.9304(2) 0.69802(10) 0.0554(5) Uani 1 1 d . . . H7C H -0.0182 0.9514 0.7201 0.066 Uiso 1 1 calc R . . C8C C 0.2006(2) 1.0030(2) 0.70063(11) 0.0583(5) Uani 1 1 d . . . H8C H 0.1606 1.0736 0.7249 0.070 Uiso 1 1 calc R . . C9C C 0.3648(2) 0.97345(17) 0.66801(9) 0.0451(4) Uani 1 1 d . . . H9C H 0.4366 1.0243 0.6700 0.054 Uiso 1 1 calc R . . C10C C 0.66841(19) 0.94204(16) 0.56168(8) 0.0368(4) Uani 1 1 d . . . H10C H 0.6037 1.0342 0.5616 0.044 Uiso 1 1 calc R . . C11C C 0.82882(19) 0.90960(17) 0.52739(9) 0.0431(4) Uani 1 1 d . . . H11C H 0.8707 0.9817 0.5030 0.052 Uiso 1 1 calc R . . N1D N 0.56105(15) 0.20481(14) 0.01796(7) 0.0406(3) Uani 1 1 d . . . C1D C 0.66253(19) 0.07657(18) 0.01994(9) 0.0429(4) Uani 1 1 d . . . H1D H 0.6235 0.0270 -0.0040 0.051 Uiso 1 1 calc R . . C2D C 0.82071(18) 0.01233(16) 0.05487(8) 0.0365(3) Uani 1 1 d . . . H2D H 0.8864 -0.0800 0.0558 0.044 Uiso 1 1 calc R . . C3D C 1.1231(2) -0.11934(17) 0.15710(9) 0.0463(4) Uani 1 1 d . . . H3D H 1.0549 -0.1743 0.1579 0.056 Uiso 1 1 calc R . . C4D C 1.2865(3) -0.17835(19) 0.18867(12) 0.0631(6) Uani 1 1 d . . . H4D H 1.3303 -0.2737 0.2107 0.076 Uiso 1 1 calc R . . C5D C 1.3863(2) -0.09985(19) 0.18844(11) 0.0587(5) Uani 1 1 d . . . H5D H 1.4981 -0.1409 0.2105 0.070 Uiso 1 1 calc R . . C6D C 1.3238(2) 0.03824(18) 0.15616(9) 0.0439(4) Uani 1 1 d . . . H6D H 1.3923 0.0926 0.1561 0.053 Uiso 1 1 calc R . . C7D C 1.16081(19) 0.09808(16) 0.12370(8) 0.0351(3) Uani 1 1 d . . . H7D H 1.1190 0.1932 0.1010 0.042 Uiso 1 1 calc R . . C8D C 0.77832(19) 0.21673(15) 0.08656(8) 0.0352(3) Uani 1 1 d . . . H8D H 0.8149 0.2695 0.1092 0.042 Uiso 1 1 calc R . . C9D C 0.62020(19) 0.27234(16) 0.05139(8) 0.0396(4) Uani 1 1 d . . . H9D H 0.5496 0.3636 0.0509 0.047 Uiso 1 1 calc R . . C10D C 0.88416(17) 0.08299(14) 0.08885(7) 0.0300(3) Uani 1 1 d . . . C11D C 1.05798(18) 0.02004(15) 0.12416(8) 0.0311(3) Uani 1 1 d . . . H1AN H 1.006(2) 0.572(2) 0.2598(11) 0.060(6) Uiso 1 1 d . . . H2AN H 1.042(2) 0.6257(18) 0.3189(10) 0.051(5) Uiso 1 1 d . . . H1AO H 0.140(3) 0.735(2) 0.4892(13) 0.094(7) Uiso 1 1 d . . . H1BN H 0.499(2) 0.308(2) 0.2404(11) 0.057(6) Uiso 1 1 d . . . H2BN H 0.544(2) 0.4232(18) 0.1859(10) 0.048(5) Uiso 1 1 d . . . H1BO H -0.366(3) 0.723(2) 0.0180(12) 0.088(7) 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 N1A 0.0343(7) 0.0550(9) 0.0423(8) -0.0227(7) 0.0067(6) -0.0200(7) O1A 0.0340(6) 0.0557(7) 0.0593(7) -0.0238(6) -0.0002(5) -0.0233(5) O2A 0.0290(6) 0.0597(8) 0.0539(7) -0.0313(6) 0.0073(5) -0.0171(5) C1A 0.0277(7) 0.0258(7) 0.0309(7) -0.0052(6) -0.0046(6) -0.0090(6) C2A 0.0346(8) 0.0311(8) 0.0320(8) -0.0084(6) -0.0056(6) -0.0160(6) C3A 0.0385(8) 0.0348(8) 0.0294(7) -0.0122(6) -0.0003(6) -0.0148(7) C4A 0.0278(7) 0.0267(7) 0.0325(7) -0.0074(6) -0.0013(6) -0.0078(6) C5A 0.0278(7) 0.0361(8) 0.0403(8) -0.0178(7) -0.0033(6) -0.0113(6) C6A 0.0288(7) 0.0332(8) 0.0349(8) -0.0154(7) -0.0022(6) -0.0083(6) C7A 0.0298(8) 0.0309(8) 0.0362(8) -0.0071(7) -0.0041(6) -0.0110(6) N1B 0.0323(7) 0.0476(9) 0.0369(8) 0.0000(7) -0.0070(6) -0.0144(7) O1B 0.0311(6) 0.0457(7) 0.0611(7) -0.0075(6) -0.0009(5) -0.0208(5) O2B 0.0281(6) 0.0458(7) 0.0525(7) 0.0052(6) -0.0087(5) -0.0116(5) C1B 0.0263(7) 0.0278(7) 0.0305(7) -0.0102(6) 0.0032(6) -0.0107(6) C2B 0.0325(8) 0.0296(8) 0.0305(7) -0.0094(6) 0.0049(6) -0.0160(6) C3B 0.0373(8) 0.0276(7) 0.0253(7) -0.0040(6) -0.0001(6) -0.0119(6) C4B 0.0272(7) 0.0309(8) 0.0267(7) -0.0108(6) 0.0004(6) -0.0070(6) C5B 0.0264(7) 0.0316(8) 0.0376(8) -0.0067(7) 0.0037(6) -0.0135(6) C6B 0.0282(7) 0.0263(7) 0.0338(8) -0.0016(6) 0.0007(6) -0.0089(6) C7B 0.0274(7) 0.0322(8) 0.0368(8) -0.0119(7) 0.0027(6) -0.0108(6) N1C 0.0286(7) 0.0487(8) 0.0397(7) -0.0106(6) -0.0012(5) -0.0122(6) C1C 0.0373(8) 0.0376(9) 0.0357(8) -0.0123(7) -0.0021(7) -0.0062(7) C2C 0.0398(8) 0.0319(8) 0.0291(7) -0.0062(6) 0.0014(6) -0.0125(7) C3C 0.0318(7) 0.0321(8) 0.0241(7) -0.0040(6) -0.0041(6) -0.0099(6) C4C 0.0339(8) 0.0309(8) 0.0245(7) -0.0006(6) -0.0010(6) -0.0087(6) C5C 0.0399(8) 0.0415(9) 0.0261(7) -0.0030(7) -0.0016(6) -0.0154(7) C6C 0.0412(9) 0.0578(11) 0.0325(8) -0.0002(8) 0.0001(7) -0.0227(8) C7C 0.0440(10) 0.0653(13) 0.0463(10) -0.0099(9) 0.0165(8) -0.0151(9) C8C 0.0620(12) 0.0510(11) 0.0601(12) -0.0237(10) 0.0241(9) -0.0175(9) C9C 0.0503(10) 0.0389(9) 0.0460(10) -0.0131(8) 0.0107(8) -0.0170(8) C10C 0.0314(8) 0.0310(8) 0.0445(9) -0.0042(7) -0.0044(7) -0.0100(6) C11C 0.0310(8) 0.0424(10) 0.0525(10) -0.0014(8) -0.0038(7) -0.0161(7) N1D 0.0273(7) 0.0496(8) 0.0392(7) -0.0096(6) 0.0001(5) -0.0082(6) C1D 0.0302(8) 0.0532(11) 0.0524(10) -0.0240(8) 0.0036(7) -0.0162(8) C2D 0.0286(8) 0.0348(8) 0.0467(9) -0.0160(7) 0.0031(6) -0.0087(6) C3D 0.0498(10) 0.0340(9) 0.0519(10) -0.0036(8) -0.0146(8) -0.0126(8) C4D 0.0645(12) 0.0347(10) 0.0796(14) -0.0003(10) -0.0357(11) -0.0057(9) C5D 0.0455(10) 0.0519(12) 0.0707(13) -0.0130(10) -0.0268(9) -0.0022(9) C6D 0.0386(9) 0.0507(10) 0.0459(10) -0.0173(8) -0.0036(7) -0.0149(8) C7D 0.0383(8) 0.0337(8) 0.0324(8) -0.0106(7) 0.0012(6) -0.0105(7) C8D 0.0372(8) 0.0327(8) 0.0327(8) -0.0101(7) -0.0019(6) -0.0070(7) C9D 0.0362(8) 0.0352(9) 0.0366(8) -0.0069(7) 0.0009(7) -0.0019(7) C10D 0.0292(7) 0.0309(8) 0.0263(7) -0.0063(6) 0.0037(6) -0.0083(6) C11D 0.0323(8) 0.0308(8) 0.0285(7) -0.0094(6) 0.0011(6) -0.0080(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 N1A C4A 1.3780(19) . ? O1A C7A 1.2189(16) . ? O2A C7A 1.3214(18) . ? C1A C2A 1.3895(19) . ? C1A C6A 1.3959(18) . ? C1A C7A 1.4796(19) . ? C2A C3A 1.374(2) . ? C3A C4A 1.3995(19) . ? C4A C5A 1.400(2) . ? C5A C6A 1.3753(19) . ? N1B C4B 1.3717(18) . ? O1B C7B 1.2213(16) . ? O2B C7B 1.3149(18) . ? C1B C2B 1.3912(19) . ? C1B C6B 1.3971(18) . ? C1B C7B 1.4799(19) . ? C2B C3B 1.3809(19) . ? C3B C4B 1.4003(19) . ? C4B C5B 1.3958(19) . ? C5B C6B 1.3779(19) . ? N1C C1C 1.334(2) . ? N1C C11C 1.337(2) . ? C1C C2C 1.380(2) . ? C2C C3C 1.391(2) . ? C3C C10C 1.392(2) . ? C3C C4C 1.485(2) . ? C4C C5C 1.393(2) . ? C4C C9C 1.394(2) . ? C5C C6C 1.386(2) . ? C6C C7C 1.383(3) . ? C7C C8C 1.379(3) . ? C8C C9C 1.384(2) . ? C10C C11C 1.373(2) . ? N1D C9D 1.334(2) . ? N1D C1D 1.334(2) . ? C1D C2D 1.376(2) . ? C2D C10D 1.391(2) . ? C3D C4D 1.383(2) . ? C3D C11D 1.391(2) . ? C4D C5D 1.377(3) . ? C5D C6D 1.377(2) . ? C6D C7D 1.387(2) . ? C7D C11D 1.392(2) . ? C8D C9D 1.378(2) . ? C8D C10D 1.391(2) . ? C10D C11D 1.4851(19) . ? N1A H1AN 0.90(2) . ? N1A N2AN 0.877(18) . ? O2A H1AO 0.95(3) . ? C2A H2A 0.950 . ? C3A H3A 0.950 . ? C5A H5A 0.950 . ? C6A H6A 0.950 . ? N1B H1BN 0.86(2) . ? N1B H2BN 0.905(18) . ? O2B H1BO 1.01(3) . ? C2B H2B 0.950 . ? C3B H3B 0.950 . ? C5B H5B 0.950 . ? C6B H6B 0.950 . ? C1C H1C 0.950 . ? C2C H2C 0.950 . ? C5C H5C 0.950 . ? C6C H6C 0.950 . ? C7C H7C 0.950 . ? C8C H8C 0.950 . ? C9C H9C 0.950 . ? C10C H10C 0.950 . ? C11C H11C 0.950 . ? C1D H1D 0.950 . ? C2D H2D 0.950 . ? C3D H3D 0.950 . ? C4D H4D 0.950 . ? C5D H5D 0.950 . ? C6D H6D 0.950 . ? C7D H7D 0.950 . ? C8D H8D 0.950 . ? C9D H9D 0.950 . ? 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 C2A C1A C6A 117.93(12) . . ? C2A C1A C7A 120.06(12) . . ? C6A C1A C7A 121.97(12) . . ? C3A C2A C1A 121.45(12) . . ? C2A C3A C4A 120.60(13) . . ? N1A C4A C3A 121.58(13) . . ? N1A C4A C5A 120.31(13) . . ? C3A C4A C5A 118.08(12) . . ? C6A C5A C4A 120.66(12) . . ? C5A C6A C1A 121.17(13) . . ? O1A C7A O2A 122.60(13) . . ? O1A C7A C1A 123.42(13) . . ? O2A C7A C1A 113.96(12) . . ? C2B C1B C6B 118.00(12) . . ? C2B C1B C7B 120.24(12) . . ? C6B C1B C7B 121.74(12) . . ? C3B C2B C1B 121.38(12) . . ? C2B C3B C4B 120.33(13) . . ? N1B C4B C5B 119.98(13) . . ? N1B C4B C3B 121.54(13) . . ? C5B C4B C3B 118.45(12) . . ? C6B C5B C4B 120.70(12) . . ? C5B C6B C1B 121.11(13) . . ? O1B C7B O2B 122.79(13) . . ? O1B C7B C1B 122.90(13) . . ? O2B C7B C1B 114.30(12) . . ? C1C N1C C11C 116.74(13) . . ? N1C C1C C2C 123.48(14) . . ? C1C C2C C3C 119.71(14) . . ? C2C C3C C10C 116.64(13) . . ? C2C C3C C4C 121.68(13) . . ? C10C C3C C4C 121.67(13) . . ? C5C C4C C9C 118.50(14) . . ? C5C C4C C3C 120.81(13) . . ? C9C C4C C3C 120.69(13) . . ? C6C C5C C4C 120.59(15) . . ? C7C C6C C5C 120.17(16) . . ? C8C C7C C6C 119.79(16) . . ? C7C C8C C9C 120.29(17) . . ? C8C C9C C4C 120.64(16) . . ? C11C C10C C3C 119.71(14) . . ? N1C C11C C10C 123.71(15) . . ? C9D N1D C1D 116.91(13) . . ? N1D C1D C2D 123.46(15) . . ? C1D C2D C10D 119.82(14) . . ? C4D C3D C11D 120.39(15) . . ? C5D C4D C3D 120.49(17) . . ? C6D C5D C4D 119.88(15) . . ? C5D C6D C7D 120.04(15) . . ? C6D C7D C11D 120.62(14) . . ? C9D C8D C10D 119.75(14) . . ? N1D C9D C8D 123.46(14) . . ? C2D C10D C8D 116.58(13) . . ? C2D C10D C11D 121.71(13) . . ? C8D C10D C11D 121.69(13) . . ? C3D C11D C7D 118.57(13) . . ? C3D C11D C10D 120.43(13) . . ? C7D C11D C10D 120.98(13) . . ? C4A N1A H1AN 119.0(12) . . ? C4A N1A H2AN 115.6(12) . . ? H1AN N1A H2AN 117.0(17) . . ? C7A O2A H1AO 107.8(14) . . ? C1A C2A H2A 119.00 . . ? C3A C2A H2A 119.00 . . ? C4A C3A H3A 120.00 . . ? C2A C3A H3A 120.00 . . ? C4A C5A H5A 120.00 . . ? C6A C5A H5A 120.00 . . ? C1A C6A H6A 119.00 . . ? C5A C6A H6A 119.00 . . ? H1BN N1B H2BN 118.4(17) . . ? C4B N1B H2BN 117.6(12) . . ? C4B N1B H1BN 117.5(12) . . ? C7B O2B H1BO 110.4(13) . . ? C1B C2B H2B 119.00 . . ? C3B C2B H2B 119.00 . . ? C2B C3B H3B 120.00 . . ? C6B C5B H5B 120.00 . . ? C4B C3B H3B 120.00 . . ? C1B C6B H6B 119.00 . . ? C4B C5B H5B 120.00 . . ? C5B C6B H6B 119.00 . . ? C2C C1C H1C 118.00 . . ? N1C C1C H1C 118.00 . . ? C1C C2C H2C 120.00 . . ? C3C C2C H2C 120.00 . . ? C4C C5C H5C 120.00 . . ? C6C C5C H5C 120.00 . . ? C5C C6C H6C 120.00 . . ? C7C C6C H6C 120.00 . . ? C6C C7C H7C 120.00 . . ? C8C C7C H7C 120.00 . . ? C7C C8C H8C 120.00 . . ? C9C C8C H8C 120.00 . . ? C4C C9C H9C 120.00 . . ? C8C C9C H9C 120.00 . . ? C3C C10C H10C 120.00 . . ? C11C C10C H10C 120.00 . . ? C10C C11C H11C 118.00 . . ? N1C C11C H11C 118.00 . . ? C2D C1D H1D 118.00 . . ? N1D C1D H1D 118.00 . . ? C1D C2D H2D 120.00 . . ? C10D C2D H2D 120.00 . . ? C4D C3D H3D 120.00 . . ? C11D C3D H3D 120.00 . . ? C5D C4D H4D 120.00 . . ? C3D C4D H4D 120.00 . . ? C4D C5D H5D 120.00 . . ? C6D C5D H5D 120.00 . . ? C7D C6D H6D 120.00 . . ? C5D C6D H6D 120.00 . . ? C11D C7D H7D 120.00 . . ? C6D C7D H7D 120.00 . . ? C10D C8D H8D 120.00 . . ? C9D C8D H8D 120.00 . . ? N1D C9D H9D 118.00 . . ? C8D C9D H9D 118.00 . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.180 _refine_diff_density_min -0.266 _refine_diff_density_rms 0.056 _database_code_depnum_ccdc_archive 'CCDC 923464' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_publication_text #END data_35dnba_4pp #TrackingRef '19639_web_deposit_cif_file_0_ColinSeaton_1366368486.compiled_cifs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-phenylpyridinium 3,5-dinitrobenzoate 3,5-dinitrobenzoic acid ; _chemical_name_common '4-phenylpyridinium 3,5-dinitrobenzoate 3,5-dinitrobenzoic acid' _chemical_melting_point ? _chemical_formula_moiety 'C7 H3 N2 O6, C7 H4 N2 O6, C11 H10 N' _chemical_formula_sum 'C25 H17 N5 O12' _chemical_formula_weight 579.44 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 triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.5861(9) _cell_length_b 10.1179(9) _cell_length_c 14.4262(11) _cell_angle_alpha 88.676(7) _cell_angle_beta 76.576(7) _cell_angle_gamma 64.447(9) _cell_volume 1223.1(2) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3039 _cell_measurement_theta_min 3.0704 _cell_measurement_theta_max 28.4190 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 1.2 _exptl_crystal_size_mid 1.0 _exptl_crystal_size_min 0.7 #Data collected with a 1 mm collimator. _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.573 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 596 _exptl_absorpt_coefficient_mu 0.129 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.80539 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.33.31 (release 08-01-2009 CrysAlis171 .NET) (compiled Jan 8 2009,16:24:04) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; 'Goniometer KM4/Xcalibur, detector: Sapphire2 (large Be window)' ; _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8.3367 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7640 _diffrn_reflns_av_R_equivalents 0.0283 _diffrn_reflns_av_sigmaI/netI 0.0739 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.07 _diffrn_reflns_theta_max 28.46 _reflns_number_total 5340 _reflns_number_gt 3272 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.31 (release 08-01-2009 CrysAlis171 .NET) (compiled Jan 8 2009,16:24:04) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.31 (release 08-01-2009 CrysAlis171 .NET) (compiled Jan 8 2009,16:24:04) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.31 (release 08-01-2009 CrysAlis171 .NET) (compiled Jan 8 2009,16:24:04) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0330P)^2^+0.0000P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5340 _refine_ls_number_parameters 447 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0721 _refine_ls_R_factor_gt 0.0374 _refine_ls_wR_factor_ref 0.0757 _refine_ls_wR_factor_gt 0.0701 _refine_ls_goodness_of_fit_ref 0.838 _refine_ls_restrained_S_all 0.838 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 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 O1A O 0.11449(14) 0.58423(13) 0.25299(8) 0.0225(3) Uani 1 1 d . . . O2A O 0.21833(14) 0.45702(13) 0.37022(8) 0.0238(3) Uani 1 1 d . . . O3A O -0.12125(15) 0.34121(14) 0.08560(8) 0.0279(3) Uani 1 1 d . . . O4A O -0.21045(15) 0.19377(14) 0.15952(9) 0.0300(3) Uani 1 1 d . . . O5A O -0.05377(14) 0.19379(14) 0.55209(8) 0.0243(3) Uani 1 1 d . . . O6A O -0.19597(14) 0.11814(13) 0.49089(8) 0.0246(3) Uani 1 1 d . . . N1A N -0.14865(17) 0.27779(15) 0.15643(10) 0.0207(3) Uani 1 1 d . . . N2A N -0.11375(16) 0.18434(15) 0.48722(10) 0.0193(3) Uani 1 1 d . . . C1A C 0.13033(19) 0.49041(19) 0.31201(12) 0.0182(4) Uani 1 1 d . . . C2A C 0.03384(18) 0.40407(17) 0.31613(11) 0.0156(4) Uani 1 1 d . . . C3A C -0.01873(19) 0.38752(18) 0.23716(12) 0.0164(4) Uani 1 1 d . . . C4A C -0.10087(19) 0.30313(18) 0.24222(11) 0.0167(4) Uani 1 1 d . . . C5A C -0.13762(19) 0.23728(18) 0.32331(12) 0.0155(4) Uani 1 1 d . . . C6A C -0.08390(19) 0.25680(18) 0.40017(11) 0.0154(4) Uani 1 1 d . . . C7A C 0.00137(19) 0.33788(18) 0.39858(12) 0.0150(4) Uani 1 1 d . . . O1B O 0.39283(14) 0.56477(13) 0.39639(8) 0.0222(3) Uani 1 1 d . . . O2B O 0.53947(14) 0.52896(14) 0.24450(9) 0.0261(3) Uani 1 1 d . . . O3B O 0.84821(16) 0.81793(16) 0.16761(9) 0.0380(4) Uani 1 1 d . . . O4B O 0.88634(14) 0.92447(13) 0.28138(8) 0.0229(3) Uani 1 1 d . . . O5B O 0.64931(14) 0.90292(14) 0.60870(8) 0.0257(3) Uani 1 1 d . . . O6B O 0.47361(14) 0.81717(14) 0.64237(8) 0.0244(3) Uani 1 1 d . . . N1B N 0.82994(17) 0.85061(16) 0.25193(10) 0.0216(3) Uani 1 1 d . . . N2B N 0.57764(17) 0.83833(15) 0.58617(10) 0.0189(3) Uani 1 1 d . . . C1B C 0.5019(2) 0.57604(18) 0.32781(12) 0.0178(4) Uani 1 1 d . . . C2B C 0.57789(19) 0.66342(18) 0.36153(12) 0.0162(4) Uani 1 1 d . . . C3B C 0.6700(2) 0.71181(19) 0.29338(12) 0.0171(4) Uani 1 1 d . . . C4B C 0.73398(19) 0.79733(18) 0.32417(11) 0.0166(4) Uani 1 1 d . . . C5B C 0.7107(2) 0.83642(18) 0.41937(12) 0.0162(4) Uani 1 1 d . . . C6B C 0.61629(19) 0.78831(18) 0.48460(11) 0.0160(4) Uani 1 1 d . . . C7B C 0.5505(2) 0.70207(18) 0.45781(12) 0.0165(4) Uani 1 1 d . . . N1C N 0.22108(17) 0.77608(17) 0.17630(11) 0.0220(3) Uani 1 1 d . . . C1C C 0.2239(2) 0.8132(2) 0.08663(13) 0.0232(4) Uani 1 1 d . . . C2C C 0.2577(2) 0.92793(19) 0.05644(13) 0.0197(4) Uani 1 1 d . . . C3C C 0.29081(19) 1.00742(18) 0.11931(11) 0.0164(4) Uani 1 1 d . . . C4C C 0.2837(2) 0.9659(2) 0.21275(13) 0.0209(4) Uani 1 1 d . . . C5C C 0.2482(2) 0.8513(2) 0.23961(13) 0.0217(4) Uani 1 1 d . . . C6C C 0.32535(19) 1.13380(18) 0.09107(11) 0.0164(4) Uani 1 1 d . . . C7C C 0.2721(2) 1.2123(2) 0.01563(13) 0.0244(4) Uani 1 1 d . . . C8C C 0.2952(3) 1.3361(2) -0.00701(14) 0.0315(5) Uani 1 1 d . . . C9C C 0.3711(2) 1.3837(2) 0.04513(15) 0.0330(5) Uani 1 1 d . . . C10C C 0.4264(2) 1.3065(2) 0.11933(14) 0.0277(5) Uani 1 1 d . . . C11C C 0.4038(2) 1.1824(2) 0.14254(13) 0.0222(4) Uani 1 1 d . . . H5A H -0.1931(18) 0.1791(18) 0.3250(10) 0.015(4) Uiso 1 1 d . . . H3B H 0.6852(18) 0.6883(17) 0.2272(11) 0.015(4) Uiso 1 1 d . . . H7B H 0.4843(18) 0.6741(17) 0.5043(11) 0.011(4) Uiso 1 1 d . . . H7A H 0.0399(17) 0.3471(16) 0.4527(11) 0.009(4) Uiso 1 1 d . . . H3A H 0.0045(17) 0.4315(17) 0.1804(11) 0.012(4) Uiso 1 1 d . . . H2C H 0.266(2) 0.9475(19) -0.0092(13) 0.026(5) Uiso 1 1 d . . . H1CA H 0.2048(19) 0.7562(19) 0.0432(11) 0.018(5) Uiso 1 1 d . . . H5C H 0.239(2) 0.8219(19) 0.3041(12) 0.031(5) Uiso 1 1 d . . . H5B H 0.752(2) 0.8954(19) 0.4385(11) 0.022(5) Uiso 1 1 d . . . H11C H 0.443(2) 1.131(2) 0.1952(12) 0.029(5) Uiso 1 1 d . . . H4C H 0.301(2) 1.018(2) 0.2567(12) 0.027(5) Uiso 1 1 d . . . H10C H 0.481(2) 1.336(2) 0.1582(13) 0.038(6) Uiso 1 1 d . . . H7C H 0.2141(19) 1.1866(18) -0.0191(11) 0.018(5) Uiso 1 1 d . . . H1C H 0.195(2) 0.700(2) 0.2012(13) 0.039(6) Uiso 1 1 d . . . H8C H 0.250(2) 1.390(2) -0.0599(13) 0.041(6) Uiso 1 1 d . . . H9C H 0.381(2) 1.476(2) 0.0327(13) 0.043(6) Uiso 1 1 d . . . H2A H 0.319(3) 0.525(3) 0.3756(17) 0.087(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 O1A 0.0247(7) 0.0207(7) 0.0260(7) 0.0050(6) -0.0050(5) -0.0143(6) O2A 0.0227(7) 0.0273(7) 0.0295(7) 0.0028(6) -0.0110(6) -0.0159(6) O3A 0.0350(8) 0.0358(8) 0.0193(7) 0.0065(6) -0.0116(6) -0.0190(7) O4A 0.0408(8) 0.0282(8) 0.0351(8) 0.0035(6) -0.0196(6) -0.0228(7) O5A 0.0219(7) 0.0341(8) 0.0187(7) 0.0074(6) -0.0096(5) -0.0118(6) O6A 0.0260(7) 0.0232(7) 0.0285(7) 0.0041(6) -0.0023(5) -0.0165(6) N1A 0.0204(8) 0.0197(9) 0.0238(9) 0.0003(7) -0.0098(7) -0.0082(7) N2A 0.0168(8) 0.0173(8) 0.0214(8) 0.0019(6) -0.0024(6) -0.0063(7) C1A 0.0153(9) 0.0175(9) 0.0192(10) -0.0057(7) 0.0015(7) -0.0075(7) C2A 0.0124(9) 0.0136(9) 0.0192(9) -0.0018(7) -0.0027(7) -0.0046(7) C3A 0.0153(9) 0.0142(9) 0.0178(9) 0.0029(7) -0.0034(7) -0.0051(7) C4A 0.0158(9) 0.0140(9) 0.0178(9) -0.0039(7) -0.0071(7) -0.0026(7) C5A 0.0149(9) 0.0104(9) 0.0213(9) -0.0015(7) -0.0046(7) -0.0056(7) C6A 0.0137(9) 0.0141(9) 0.0170(9) 0.0014(7) -0.0022(7) -0.0055(7) C7A 0.0131(9) 0.0162(9) 0.0152(9) -0.0005(7) -0.0060(7) -0.0047(7) O1B 0.0212(7) 0.0272(7) 0.0250(7) 0.0000(6) -0.0063(5) -0.0164(6) O2B 0.0265(7) 0.0297(8) 0.0258(7) -0.0062(6) -0.0067(6) -0.0152(6) O3B 0.0506(9) 0.0661(11) 0.0173(7) 0.0089(7) -0.0128(6) -0.0419(8) O4B 0.0220(7) 0.0204(7) 0.0298(7) 0.0014(6) -0.0061(5) -0.0126(6) O5B 0.0307(7) 0.0313(8) 0.0235(7) -0.0021(6) -0.0107(6) -0.0191(6) O6B 0.0206(7) 0.0353(8) 0.0180(7) 0.0007(6) -0.0024(5) -0.0140(6) N1B 0.0210(8) 0.0243(9) 0.0224(9) 0.0052(7) -0.0089(6) -0.0109(7) N2B 0.0190(8) 0.0193(8) 0.0195(8) -0.0005(6) -0.0082(6) -0.0077(7) C1B 0.0161(9) 0.0144(9) 0.0230(10) -0.0003(8) -0.0097(8) -0.0042(7) C2B 0.0138(9) 0.0134(9) 0.0210(9) -0.0008(7) -0.0072(7) -0.0040(7) C3B 0.0175(9) 0.0187(9) 0.0143(9) -0.0022(7) -0.0057(7) -0.0061(7) C4B 0.0149(9) 0.0170(9) 0.0176(9) 0.0018(7) -0.0043(7) -0.0066(7) C5B 0.0134(9) 0.0138(9) 0.0232(10) 0.0012(7) -0.0091(7) -0.0053(7) C6B 0.0152(9) 0.0169(9) 0.0154(9) -0.0001(7) -0.0075(7) -0.0046(7) C7B 0.0127(9) 0.0170(9) 0.0195(9) 0.0006(7) -0.0046(7) -0.0059(7) N1C 0.0196(8) 0.0203(9) 0.0256(9) 0.0027(7) -0.0017(7) -0.0104(7) C1C 0.0215(10) 0.0244(11) 0.0242(11) -0.0031(8) -0.0053(8) -0.0103(8) C2C 0.0193(10) 0.0232(10) 0.0161(10) -0.0003(8) -0.0037(7) -0.0092(8) C3C 0.0120(8) 0.0190(9) 0.0147(9) -0.0008(7) -0.0015(7) -0.0044(7) C4C 0.0233(10) 0.0238(10) 0.0165(10) -0.0002(8) -0.0067(8) -0.0101(8) C5C 0.0207(10) 0.0234(10) 0.0178(10) 0.0029(8) -0.0023(8) -0.0081(8) C6C 0.0169(9) 0.0169(9) 0.0130(9) -0.0016(7) -0.0003(7) -0.0069(7) C7C 0.0304(11) 0.0220(10) 0.0197(10) -0.0008(8) -0.0068(8) -0.0100(9) C8C 0.0428(13) 0.0220(11) 0.0235(11) 0.0052(9) -0.0034(9) -0.0111(10) C9C 0.0355(12) 0.0202(11) 0.0358(12) -0.0033(9) 0.0094(9) -0.0142(9) C10C 0.0227(10) 0.0264(11) 0.0327(12) -0.0101(9) 0.0020(9) -0.0135(9) C11C 0.0177(9) 0.0232(10) 0.0226(10) -0.0033(8) -0.0020(8) -0.0073(8) _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 O1A C1A 1.2439(19) . ? O2A C1A 1.2653(19) . ? O2A H2A 1.42(3) . ? O3A N1A 1.2309(17) . ? O4A N1A 1.2232(17) . ? O5A N2A 1.2316(17) . ? O6A N2A 1.2277(17) . ? N1A C4A 1.479(2) . ? N2A C6A 1.472(2) . ? C1A C2A 1.514(2) . ? C2A C3A 1.388(2) . ? C2A C7A 1.390(2) . ? C3A C4A 1.380(2) . ? C3A H3A 0.950(15) . ? C4A C5A 1.383(2) . ? C5A C6A 1.377(2) . ? C5A H5A 0.945(16) . ? C6A C7A 1.382(2) . ? C7A H7A 0.961(15) . ? O1B C1B 1.3047(19) . ? O1B H2A 1.05(3) . ? O2B C1B 1.2159(19) . ? O3B N1B 1.2205(17) . ? O4B N1B 1.2252(18) . ? O5B N2B 1.2270(17) . ? O6B N2B 1.2241(16) . ? N1B C4B 1.476(2) . ? N2B C6B 1.470(2) . ? C1B C2B 1.513(2) . ? C2B C7B 1.385(2) . ? C2B C3B 1.390(2) . ? C3B C4B 1.387(2) . ? C3B H3B 0.951(16) . ? C4B C5B 1.378(2) . ? C5B C6B 1.380(2) . ? C5B H5B 0.925(18) . ? C6B C7B 1.383(2) . ? C7B H7B 0.939(15) . ? N1C C1C 1.336(2) . ? N1C C5C 1.340(2) . ? N1C H1C 0.95(2) . ? C1C C2C 1.370(2) . ? C1C H1CA 0.959(17) . ? C2C C3C 1.399(2) . ? C2C H2C 0.955(17) . ? C3C C4C 1.398(2) . ? C3C C6C 1.480(2) . ? C4C C5C 1.367(2) . ? C4C H4C 0.926(18) . ? C5C H5C 0.966(17) . ? C6C C7C 1.394(2) . ? C6C C11C 1.398(2) . ? C7C C8C 1.382(3) . ? C7C H7C 0.942(16) . ? C8C C9C 1.379(3) . ? C8C H8C 1.001(19) . ? C9C C10C 1.380(3) . ? C9C H9C 0.98(2) . ? C10C C11C 1.384(3) . ? C10C H10C 0.97(2) . ? C11C H11C 0.967(17) . ? 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 C1A O2A H2A 122.8(10) . . ? O4A N1A O3A 124.05(14) . . ? O4A N1A C4A 118.28(14) . . ? O3A N1A C4A 117.65(14) . . ? O6A N2A O5A 123.96(14) . . ? O6A N2A C6A 118.46(14) . . ? O5A N2A C6A 117.57(14) . . ? O1A C1A O2A 127.93(16) . . ? O1A C1A C2A 117.23(15) . . ? O2A C1A C2A 114.83(14) . . ? C3A C2A C7A 119.90(15) . . ? C3A C2A C1A 120.34(14) . . ? C7A C2A C1A 119.74(15) . . ? C4A C3A C2A 118.73(15) . . ? C4A C3A H3A 121.1(10) . . ? C2A C3A H3A 120.1(10) . . ? C3A C4A C5A 123.16(16) . . ? C3A C4A N1A 118.94(14) . . ? C5A C4A N1A 117.88(15) . . ? C6A C5A C4A 116.29(15) . . ? C6A C5A H5A 121.9(9) . . ? C4A C5A H5A 121.8(9) . . ? C5A C6A C7A 123.04(15) . . ? C5A C6A N2A 118.78(15) . . ? C7A C6A N2A 118.14(15) . . ? C6A C7A C2A 118.86(16) . . ? C6A C7A H7A 121.1(9) . . ? C2A C7A H7A 120.1(9) . . ? C1B O1B H2A 116.3(14) . . ? O3B N1B O4B 124.61(14) . . ? O3B N1B C4B 118.17(15) . . ? O4B N1B C4B 117.21(14) . . ? O6B N2B O5B 124.07(14) . . ? O6B N2B C6B 118.51(14) . . ? O5B N2B C6B 117.39(14) . . ? O2B C1B O1B 126.68(16) . . ? O2B C1B C2B 121.02(15) . . ? O1B C1B C2B 112.26(15) . . ? C7B C2B C3B 119.94(16) . . ? C7B C2B C1B 121.37(15) . . ? C3B C2B C1B 118.60(15) . . ? C4B C3B C2B 118.62(16) . . ? C4B C3B H3B 121.6(9) . . ? C2B C3B H3B 119.8(9) . . ? C5B C4B C3B 122.97(16) . . ? C5B C4B N1B 118.27(15) . . ? C3B C4B N1B 118.75(15) . . ? C4B C5B C6B 116.57(16) . . ? C4B C5B H5B 121.8(10) . . ? C6B C5B H5B 121.6(10) . . ? C5B C6B C7B 122.78(16) . . ? C5B C6B N2B 118.05(15) . . ? C7B C6B N2B 119.08(15) . . ? C6B C7B C2B 119.10(16) . . ? C6B C7B H7B 120.1(10) . . ? C2B C7B H7B 120.7(10) . . ? C1C N1C C5C 121.12(16) . . ? C1C N1C H1C 123.9(11) . . ? C5C N1C H1C 114.9(11) . . ? N1C C1C C2C 120.72(18) . . ? N1C C1C H1CA 118.7(10) . . ? C2C C1C H1CA 120.6(10) . . ? C1C C2C C3C 120.22(17) . . ? C1C C2C H2C 118.8(11) . . ? C3C C2C H2C 120.8(11) . . ? C4C C3C C2C 116.84(16) . . ? C4C C3C C6C 120.60(16) . . ? C2C C3C C6C 122.51(15) . . ? C5C C4C C3C 120.72(17) . . ? C5C C4C H4C 120.3(11) . . ? C3C C4C H4C 118.9(11) . . ? N1C C5C C4C 120.35(17) . . ? N1C C5C H5C 116.9(11) . . ? C4C C5C H5C 122.7(11) . . ? C7C C6C C11C 118.46(16) . . ? C7C C6C C3C 120.49(16) . . ? C11C C6C C3C 120.95(15) . . ? C8C C7C C6C 120.64(19) . . ? C8C C7C H7C 117.7(10) . . ? C6C C7C H7C 121.5(10) . . ? C9C C8C C7C 120.22(19) . . ? C9C C8C H8C 123.1(11) . . ? C7C C8C H8C 116.6(11) . . ? C8C C9C C10C 120.02(19) . . ? C8C C9C H9C 120.9(11) . . ? C10C C9C H9C 118.9(11) . . ? C9C C10C C11C 120.15(19) . . ? C9C C10C H10C 123.0(11) . . ? C11C C10C H10C 116.9(11) . . ? C10C C11C C6C 120.49(18) . . ? C10C C11C H11C 118.4(11) . . ? C6C C11C H11C 121.1(11) . . ? 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 N1C H1C O1A 0.95(2) 1.73(2) 2.6689(19) 170.6(18) . O1B H2A O2A 1.05(3) 1.42(3) 2.4525(16) 166(2) . _diffrn_measured_fraction_theta_max 0.865 _diffrn_reflns_theta_full 26.32 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.250 _refine_diff_density_min -0.258 _refine_diff_density_rms 0.050 _database_code_depnum_ccdc_archive 'CCDC 923465' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_publication_text #END data_ga_4pp #TrackingRef '19639_web_deposit_cif_file_0_ColinSeaton_1366368486.compiled_cifs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-phenylpyridinium gallate ; _chemical_name_common '4-phenylpyridinium gallate' _chemical_melting_point ? _chemical_formula_moiety 'C7 H5 O5, C11 H10 N' _chemical_formula_sum 'C18 H15 N O5' _chemical_formula_weight 325.31 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 P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.0267(5) _cell_length_b 19.4733(15) _cell_length_c 10.9698(8) _cell_angle_alpha 90.00 _cell_angle_beta 102.362(3) _cell_angle_gamma 90.00 _cell_volume 1466.23(19) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 9905 _cell_measurement_theta_min 2.17 _cell_measurement_theta_max 34.67 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.95 _exptl_crystal_size_mid 0.48 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.474 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 680 _exptl_absorpt_coefficient_mu 0.109 _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 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 34992 _diffrn_reflns_av_R_equivalents 0.0230 _diffrn_reflns_av_sigmaI/netI 0.0174 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 30.51 _reflns_number_total 8734 _reflns_number_gt 8311 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0631P)^2^+0.3104P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8734 _refine_ls_number_parameters 465 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0378 _refine_ls_R_factor_gt 0.0360 _refine_ls_wR_factor_ref 0.1010 _refine_ls_wR_factor_gt 0.0993 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0.000 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 O1A O 0.42286(13) 0.24087(6) -0.23861(9) 0.01711(19) Uani 1 1 d . . . O2A O 0.70617(14) 0.19221(6) -0.15369(10) 0.01851(19) Uani 1 1 d . . . O3A O -0.05010(13) 0.10012(5) -0.03334(9) 0.01639(19) Uani 1 1 d . . . H3AO H -0.133(4) 0.1360(15) -0.076(3) 0.054(8) Uiso 1 1 d . . . O4A O 0.18288(13) 0.04843(5) 0.17658(9) 0.01429(18) Uani 1 1 d . . . H4AO H 0.078(5) 0.0805(17) 0.202(3) 0.081(10) Uiso 1 1 d . . . O5A O 0.56694(13) 0.07093(5) 0.22826(9) 0.01658(19) Uani 1 1 d . . . H5AO H 0.693(3) 0.0915(12) 0.2420(19) 0.033(6) Uiso 1 1 d . . . C1A C 0.52703(17) 0.20043(7) -0.16011(11) 0.0125(2) Uani 1 1 d . . . C2A C 0.42999(17) 0.16136(6) -0.07212(11) 0.0122(2) Uani 1 1 d . . . C3A C 0.22818(17) 0.15127(7) -0.09768(12) 0.0131(2) Uani 1 1 d . . . H3A H 0.1487 0.1698 -0.1714 0.016 Uiso 1 1 calc R . . C4A C 0.14442(17) 0.11393(6) -0.01448(12) 0.0117(2) Uani 1 1 d . . . C5A C 0.26059(17) 0.08644(6) 0.09465(12) 0.0119(2) Uani 1 1 d . . . C6A C 0.46118(17) 0.09757(7) 0.11960(11) 0.0122(2) Uani 1 1 d . . . C7A C 0.54547(17) 0.13443(7) 0.03673(12) 0.0129(2) Uani 1 1 d . . . H7A H 0.6825 0.1414 0.0542 0.016 Uiso 1 1 calc R . . O1B O 0.92113(13) 0.12188(5) 0.26108(9) 0.01577(18) Uani 1 1 d . . . O2B O 1.20006(13) 0.17476(5) 0.33927(9) 0.01747(19) Uani 1 1 d . . . O3B O 0.44788(13) 0.26492(5) 0.46428(9) 0.01662(19) Uani 1 1 d . . . H3BO H 0.383(3) 0.2391(10) 0.4144(17) 0.014(4) Uiso 1 1 d . . . O4B O 0.67936(13) 0.31471(5) 0.67582(9) 0.01408(18) Uani 1 1 d . . . H4BO H 0.587(3) 0.2945(10) 0.6917(17) 0.018(4) Uiso 1 1 d . . . O5B O 1.06450(14) 0.29141(6) 0.72736(9) 0.01685(19) Uani 1 1 d . . . H5BO H 1.176(4) 0.2763(14) 0.739(2) 0.038(6) Uiso 1 1 d . . . C1B C 1.02295(17) 0.16456(7) 0.33599(11) 0.0120(2) Uani 1 1 d . . . C2B C 0.92618(17) 0.20266(6) 0.42535(11) 0.0119(2) Uani 1 1 d . . . C3B C 0.72457(17) 0.21245(7) 0.40049(12) 0.0133(2) Uani 1 1 d . . . H3B H 0.6447 0.1936 0.3273 0.016 Uiso 1 1 calc R . . C4B C 0.64111(17) 0.25018(6) 0.48391(12) 0.0123(2) Uani 1 1 d . . . C5B C 0.75723(17) 0.27677(6) 0.59365(11) 0.0111(2) Uani 1 1 d . . . C6B C 0.95767(17) 0.26542(7) 0.61854(11) 0.0126(2) Uani 1 1 d . . . C7B C 1.04236(18) 0.22937(7) 0.53445(12) 0.0135(2) Uani 1 1 d . . . H6B H 1.1795 0.2229 0.5512 0.016 Uiso 1 1 calc R . . N1C N 0.89658(19) 0.32157(8) 0.94317(14) 0.0273(3) Uani 1 1 d . . . H1CN H 0.870(4) 0.3004(14) 0.872(3) 0.044(7) Uiso 1 1 d . . . C1C C 0.9661(2) 0.28767(8) 1.04936(15) 0.0286(3) Uani 1 1 d . . . H1C H 0.9868 0.2395 1.0474 0.034 Uiso 1 1 calc R . . C2C C 1.0079(2) 0.32195(7) 1.16123(14) 0.0227(3) Uani 1 1 d . . . H2C H 1.0592 0.2976 1.2361 0.027 Uiso 1 1 calc R . . C3C C 0.97499(18) 0.39267(7) 1.16514(12) 0.0160(2) Uani 1 1 d . . . C4C C 0.9047(2) 0.42614(8) 1.05201(13) 0.0233(3) Uani 1 1 d . . . H4C H 0.8827 0.4743 1.0506 0.028 Uiso 1 1 calc R . . C5C C 0.8672(2) 0.38916(9) 0.94194(14) 0.0281(3) Uani 1 1 d . . . H5C H 0.8202 0.4121 0.8649 0.034 Uiso 1 1 calc R . . C6C C 1.01128(19) 0.43042(7) 1.28446(12) 0.0158(2) Uani 1 1 d . . . C7C C 1.0075(2) 0.39638(8) 1.39586(13) 0.0230(3) Uani 1 1 d . . . H7C H 0.9838 0.3483 1.3952 0.028 Uiso 1 1 calc R . . C8C C 1.0384(2) 0.43236(9) 1.50767(13) 0.0293(3) Uani 1 1 d . . . H8C H 1.0345 0.4089 1.5830 0.035 Uiso 1 1 calc R . . C9C C 1.0747(2) 0.50207(10) 1.50998(16) 0.0292(3) Uani 1 1 d . . . H9C H 1.0964 0.5264 1.5868 0.035 Uiso 1 1 calc R . . C10C C 1.0796(2) 0.53672(8) 1.40002(16) 0.0275(3) Uani 1 1 d . . . H10C H 1.1048 0.5847 1.4017 0.033 Uiso 1 1 calc R . . C11C C 1.0476(2) 0.50121(7) 1.28767(13) 0.0210(3) Uani 1 1 d . . . H11C H 1.0504 0.5251 1.2125 0.025 Uiso 1 1 calc R . . N1D N 0.4023(2) 0.03977(8) 0.44219(13) 0.0276(3) Uani 1 1 d . . . H1DN H 0.366(4) 0.0641(15) 0.370(3) 0.052(8) Uiso 1 1 d . . . C1D C 0.4401(2) -0.02737(9) 0.44369(13) 0.0270(3) Uani 1 1 d . . . H1D H 0.4414 -0.0505 0.3677 0.032 Uiso 1 1 calc R . . C2D C 0.4773(2) -0.06342(8) 0.55390(12) 0.0213(3) Uani 1 1 d . . . H2D H 0.5051 -0.1112 0.5543 0.026 Uiso 1 1 calc R . . C3D C 0.47386(18) -0.02910(7) 0.66586(12) 0.0161(2) Uani 1 1 d . . . C4D C 0.4329(2) 0.04135(8) 0.65933(13) 0.0230(3) Uani 1 1 d . . . H4D H 0.4281 0.0660 0.7333 0.028 Uiso 1 1 calc R . . C5D C 0.3994(2) 0.07503(8) 0.54649(15) 0.0284(3) Uani 1 1 d . . . H5D H 0.3744 0.1230 0.5426 0.034 Uiso 1 1 calc R . . C6D C 0.51504(19) -0.06536(8) 0.78686(13) 0.0176(3) Uani 1 1 d . . . C7D C 0.4860(2) -0.13613(7) 0.79253(14) 0.0237(3) Uani 1 1 d . . . H7D H 0.4380 -0.1612 0.7180 0.028 Uiso 1 1 calc R . . C8D C 0.5270(2) -0.16996(9) 0.90669(18) 0.0314(3) Uani 1 1 d . . . H8D H 0.5068 -0.2181 0.9100 0.038 Uiso 1 1 calc R . . C9D C 0.5969(3) -0.13392(11) 1.01522(17) 0.0341(4) Uani 1 1 d . . . H9D H 0.6248 -0.1573 1.0931 0.041 Uiso 1 1 calc R . . C10D C 0.6266(3) -0.06356(10) 1.01086(14) 0.0332(3) Uani 1 1 d . . . H10D H 0.6751 -0.0388 1.0857 0.040 Uiso 1 1 calc R . . C11D C 0.5854(2) -0.02927(8) 0.89716(13) 0.0245(3) Uani 1 1 d . . . H11D H 0.6052 0.0189 0.8945 0.029 Uiso 1 1 calc R . . 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 O1A 0.0125(4) 0.0240(5) 0.0151(4) 0.0071(4) 0.0037(3) 0.0025(3) O2A 0.0119(4) 0.0230(5) 0.0214(5) 0.0077(4) 0.0052(3) 0.0015(3) O3A 0.0081(4) 0.0204(5) 0.0202(5) 0.0050(4) 0.0021(3) -0.0002(3) O4A 0.0137(4) 0.0153(4) 0.0152(4) 0.0025(4) 0.0061(3) -0.0004(3) O5A 0.0114(4) 0.0248(5) 0.0123(4) 0.0040(4) -0.0001(3) -0.0014(3) C1A 0.0122(5) 0.0135(6) 0.0120(5) -0.0003(4) 0.0027(4) -0.0004(4) C2A 0.0117(5) 0.0137(6) 0.0118(5) 0.0000(4) 0.0037(4) -0.0005(4) C3A 0.0118(5) 0.0138(5) 0.0133(5) 0.0014(4) 0.0019(4) 0.0007(4) C4A 0.0097(5) 0.0123(5) 0.0132(5) -0.0016(4) 0.0026(4) -0.0004(4) C5A 0.0123(5) 0.0128(5) 0.0115(5) -0.0009(4) 0.0046(4) -0.0003(4) C6A 0.0122(5) 0.0140(5) 0.0104(5) 0.0005(4) 0.0019(4) 0.0013(4) C7A 0.0109(5) 0.0163(6) 0.0118(5) 0.0004(4) 0.0031(4) -0.0006(4) O1B 0.0120(4) 0.0206(5) 0.0145(4) -0.0057(4) 0.0024(3) -0.0015(3) O2B 0.0116(4) 0.0208(5) 0.0206(5) -0.0059(4) 0.0048(3) -0.0032(3) O3B 0.0092(4) 0.0198(5) 0.0202(5) -0.0051(4) 0.0016(3) -0.0005(3) O4B 0.0134(4) 0.0166(4) 0.0136(4) -0.0035(3) 0.0061(3) -0.0015(3) O5B 0.0120(4) 0.0255(5) 0.0115(4) -0.0061(4) -0.0010(3) 0.0020(3) C1B 0.0119(5) 0.0140(6) 0.0100(5) 0.0007(4) 0.0020(4) 0.0018(4) C2B 0.0122(5) 0.0129(5) 0.0103(5) -0.0011(4) 0.0021(4) 0.0008(4) C3B 0.0123(5) 0.0147(6) 0.0124(5) -0.0017(4) 0.0015(4) 0.0001(4) C4B 0.0101(5) 0.0135(6) 0.0134(5) 0.0003(4) 0.0029(4) -0.0007(4) C5B 0.0112(5) 0.0121(5) 0.0103(5) -0.0004(4) 0.0030(4) -0.0001(4) C6B 0.0120(5) 0.0154(5) 0.0099(5) -0.0001(4) 0.0010(4) 0.0007(4) C7B 0.0112(5) 0.0169(6) 0.0122(5) -0.0009(4) 0.0018(4) 0.0009(4) N1C 0.0243(6) 0.0370(8) 0.0207(6) -0.0148(6) 0.0054(5) -0.0053(5) C1C 0.0305(7) 0.0236(7) 0.0306(7) -0.0129(6) 0.0042(6) 0.0016(6) C2C 0.0284(7) 0.0177(6) 0.0209(6) -0.0031(5) 0.0032(5) 0.0028(5) C3C 0.0167(5) 0.0168(6) 0.0146(6) -0.0033(5) 0.0036(4) -0.0017(4) C4C 0.0308(7) 0.0203(6) 0.0172(6) 0.0016(5) 0.0018(5) -0.0032(5) C5C 0.0312(7) 0.0370(8) 0.0149(6) -0.0014(5) 0.0023(5) -0.0073(6) C6C 0.0176(6) 0.0158(6) 0.0141(6) -0.0016(5) 0.0032(4) 0.0006(4) C7C 0.0300(7) 0.0229(6) 0.0162(5) -0.0016(4) 0.0048(5) -0.0041(5) C8C 0.0326(7) 0.0400(8) 0.0153(6) -0.0040(5) 0.0052(5) -0.0043(6) C9C 0.0257(7) 0.0368(9) 0.0238(7) -0.0159(6) 0.0026(6) 0.0017(6) C10C 0.0257(7) 0.0213(7) 0.0332(8) -0.0118(6) 0.0013(6) 0.0016(5) C11C 0.0235(6) 0.0162(6) 0.0225(6) -0.0036(5) 0.0032(5) 0.0010(5) N1D 0.0253(6) 0.0390(8) 0.0182(6) 0.0118(6) 0.0037(5) 0.0003(5) C1D 0.0277(7) 0.0377(8) 0.0154(6) -0.0005(5) 0.0044(5) -0.0044(6) C2D 0.0236(6) 0.0236(6) 0.0171(6) -0.0011(5) 0.0053(5) -0.0023(5) C3D 0.0169(6) 0.0177(6) 0.0138(6) 0.0009(5) 0.0037(4) -0.0006(4) C4D 0.0304(7) 0.0203(6) 0.0190(6) 0.0031(5) 0.0069(5) 0.0052(5) C5D 0.0307(7) 0.0267(7) 0.0288(7) 0.0120(6) 0.0086(6) 0.0082(6) C6D 0.0175(6) 0.0195(7) 0.0159(6) 0.0041(5) 0.0039(5) 0.0013(5) C7D 0.0269(7) 0.0188(6) 0.0254(7) 0.0033(5) 0.0057(5) -0.0005(5) C8D 0.0320(7) 0.0260(7) 0.0379(9) 0.0162(6) 0.0111(6) 0.0052(6) C9D 0.0283(8) 0.0485(11) 0.0260(8) 0.0211(8) 0.0070(6) 0.0100(7) C10D 0.0351(8) 0.0476(10) 0.0152(6) 0.0033(6) 0.0016(6) 0.0023(7) C11D 0.0297(7) 0.0265(6) 0.0165(6) 0.0015(5) 0.0030(5) 0.0000(5) _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 O1A C1A 1.2758(15) . ? O2A C1A 1.2559(15) . ? O3A C4A 1.3646(14) . ? O3A H3AO 0.96(3) . ? O4A C5A 1.3653(15) . ? O4A H4AO 1.05(3) . ? O5A C6A 1.3649(15) . ? O5A H5AO 0.95(2) . ? C1A C2A 1.5023(17) . ? C2A C7A 1.3945(17) . ? C2A C3A 1.3993(16) . ? C3A C4A 1.3922(17) . ? C3A H3A 0.9500 . ? C4A C5A 1.4027(17) . ? C5A C6A 1.3941(16) . ? C6A C7A 1.3867(17) . ? C7A H7A 0.9500 . ? O1B C1B 1.2751(15) . ? O2B C1B 1.2532(15) . ? O3B C4B 1.3591(14) . ? O3B H3BO 0.807(19) . ? O4B C5B 1.3671(15) . ? O4B H4BO 0.81(2) . ? O5B C6B 1.3642(15) . ? O5B H5BO 0.82(3) . ? C1B C2B 1.5030(16) . ? C2B C7B 1.3969(17) . ? C2B C3B 1.3972(16) . ? C3B C4B 1.3967(17) . ? C3B H3B 0.9500 . ? C4B C5B 1.4009(17) . ? C5B C6B 1.3937(16) . ? C6B C7B 1.3902(17) . ? C7B H6B 0.9500 . ? N1C C5C 1.332(2) . ? N1C C1C 1.337(2) . ? N1C H1CN 0.87(3) . ? C1C C2C 1.372(2) . ? C1C H1C 0.9500 . ? C2C C3C 1.3987(19) . ? C2C H2C 0.9500 . ? C3C C4C 1.395(2) . ? C3C C6C 1.4750(19) . ? C4C C5C 1.382(2) . ? C4C H4C 0.9500 . ? C5C H5C 0.9500 . ? C6C C7C 1.3954(19) . ? C6C C11C 1.401(2) . ? C7C C8C 1.389(2) . ? C7C H7C 0.9500 . ? C8C C9C 1.380(3) . ? C8C H8C 0.9500 . ? C9C C10C 1.389(3) . ? C9C H9C 0.9500 . ? C10C C11C 1.389(2) . ? C10C H10C 0.9500 . ? C11C H11C 0.9500 . ? N1D C1D 1.334(2) . ? N1D C5D 1.338(2) . ? N1D H1DN 0.91(3) . ? C1D C2D 1.374(2) . ? C1D H1D 0.9500 . ? C2D C3D 1.4031(19) . ? C2D H2D 0.9500 . ? C3D C4D 1.400(2) . ? C3D C6D 1.476(2) . ? C4D C5D 1.376(2) . ? C4D H4D 0.9500 . ? C5D H5D 0.9500 . ? C6D C11D 1.395(2) . ? C6D C7D 1.396(2) . ? C7D C8D 1.389(2) . ? C7D H7D 0.9500 . ? C8D C9D 1.379(3) . ? C8D H8D 0.9500 . ? C9D C10D 1.388(3) . ? C9D H9D 0.9500 . ? C10D C11D 1.390(2) . ? C10D H10D 0.9500 . ? C11D H11D 0.9500 . ? 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 C4A O3A H3AO 114.3(16) . . ? C5A O4A H4AO 104.9(18) . . ? C6A O5A H5AO 107.0(13) . . ? O2A C1A O1A 122.67(11) . . ? O2A C1A C2A 119.13(11) . . ? O1A C1A C2A 118.19(10) . . ? C7A C2A C3A 119.85(11) . . ? C7A C2A C1A 118.66(10) . . ? C3A C2A C1A 121.49(11) . . ? C4A C3A C2A 119.64(11) . . ? C4A C3A H3A 120.2 . . ? C2A C3A H3A 120.2 . . ? O3A C4A C3A 123.63(11) . . ? O3A C4A C5A 115.80(10) . . ? C3A C4A C5A 120.56(10) . . ? O4A C5A C6A 119.02(11) . . ? O4A C5A C4A 121.81(10) . . ? C6A C5A C4A 119.17(11) . . ? O5A C6A C7A 122.69(11) . . ? O5A C6A C5A 116.80(11) . . ? C7A C6A C5A 120.50(11) . . ? C6A C7A C2A 120.27(11) . . ? C6A C7A H7A 119.9 . . ? C2A C7A H7A 119.9 . . ? C4B O3B H3BO 112.1(13) . . ? C5B O4B H4BO 109.3(13) . . ? C6B O5B H5BO 109.3(17) . . ? O2B C1B O1B 122.59(11) . . ? O2B C1B C2B 119.22(11) . . ? O1B C1B C2B 118.18(10) . . ? C7B C2B C3B 119.90(11) . . ? C7B C2B C1B 118.66(10) . . ? C3B C2B C1B 121.43(11) . . ? C4B C3B C2B 119.63(11) . . ? C4B C3B H3B 120.2 . . ? C2B C3B H3B 120.2 . . ? O3B C4B C3B 123.55(11) . . ? O3B C4B C5B 115.87(10) . . ? C3B C4B C5B 120.56(11) . . ? O4B C5B C6B 119.14(11) . . ? O4B C5B C4B 121.65(10) . . ? C6B C5B C4B 119.21(11) . . ? O5B C6B C7B 122.30(11) . . ? O5B C6B C5B 117.14(11) . . ? C7B C6B C5B 120.55(11) . . ? C6B C7B C2B 120.12(11) . . ? C6B C7B H6B 119.9 . . ? C2B C7B H6B 119.9 . . ? C5C N1C C1C 121.58(14) . . ? C5C N1C H1CN 117.2(18) . . ? C1C N1C H1CN 121.2(18) . . ? N1C C1C C2C 120.48(15) . . ? N1C C1C H1C 119.8 . . ? C2C C1C H1C 119.8 . . ? C1C C2C C3C 120.08(14) . . ? C1C C2C H2C 120.0 . . ? C3C C2C H2C 120.0 . . ? C4C C3C C2C 117.52(13) . . ? C4C C3C C6C 121.17(13) . . ? C2C C3C C6C 121.30(13) . . ? C5C C4C C3C 119.93(14) . . ? C5C C4C H4C 120.0 . . ? C3C C4C H4C 120.0 . . ? N1C C5C C4C 120.39(15) . . ? N1C C5C H5C 119.8 . . ? C4C C5C H5C 119.8 . . ? C7C C6C C11C 118.87(13) . . ? C7C C6C C3C 120.56(13) . . ? C11C C6C C3C 120.57(13) . . ? C8C C7C C6C 120.35(14) . . ? C8C C7C H7C 119.8 . . ? C6C C7C H7C 119.8 . . ? C9C C8C C7C 120.37(15) . . ? C9C C8C H8C 119.8 . . ? C7C C8C H8C 119.8 . . ? C8C C9C C10C 120.04(15) . . ? C8C C9C H9C 120.0 . . ? C10C C9C H9C 120.0 . . ? C11C C10C C9C 119.96(15) . . ? C11C C10C H10C 120.0 . . ? C9C C10C H10C 120.0 . . ? C10C C11C C6C 120.41(15) . . ? C10C C11C H11C 119.8 . . ? C6C C11C H11C 119.8 . . ? C1D N1D C5D 122.13(14) . . ? C1D N1D H1DN 122.5(18) . . ? C5D N1D H1DN 115.1(18) . . ? N1D C1D C2D 120.77(14) . . ? N1D C1D H1D 119.6 . . ? C2D C1D H1D 119.6 . . ? C1D C2D C3D 119.43(14) . . ? C1D C2D H2D 120.3 . . ? C3D C2D H2D 120.3 . . ? C4D C3D C2D 117.63(13) . . ? C4D C3D C6D 120.87(13) . . ? C2D C3D C6D 121.50(13) . . ? C5D C4D C3D 120.44(14) . . ? C5D C4D H4D 119.8 . . ? C3D C4D H4D 119.8 . . ? N1D C5D C4D 119.58(15) . . ? N1D C5D H5D 120.2 . . ? C4D C5D H5D 120.2 . . ? C11D C6D C7D 119.12(13) . . ? C11D C6D C3D 120.24(14) . . ? C7D C6D C3D 120.64(14) . . ? C8D C7D C6D 120.26(15) . . ? C8D C7D H7D 119.9 . . ? C6D C7D H7D 119.9 . . ? C9D C8D C7D 120.25(16) . . ? C9D C8D H8D 119.9 . . ? C7D C8D H8D 119.9 . . ? C8D C9D C10D 120.07(15) . . ? C8D C9D H9D 120.0 . . ? C10D C9D H9D 120.0 . . ? C9D C10D C11D 120.08(16) . . ? C9D C10D H10D 120.0 . . ? C11D C10D H10D 120.0 . . ? C10D C11D C6D 120.23(15) . . ? C10D C11D H11D 119.9 . . ? C6D C11D H11D 119.9 . . ? 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 O3A H3AO O2A 0.96(3) 1.67(3) 2.6314(14) 174(3) 1_455 O4A H4AO O1B 1.05(3) 1.61(3) 2.6492(13) 171(3) 1_455 O4A H4AO O2B 1.05(3) 2.41(3) 3.0265(14) 116(2) 1_455 O5A H5AO O1B 0.95(2) 1.68(2) 2.6315(14) 175(2) . O3B H3BO O2B 0.807(19) 1.858(19) 2.6407(14) 163.1(18) 1_455 O4B H4BO O1A 0.81(2) 1.84(2) 2.6309(14) 165.8(19) 1_556 O4B H4BO O2A 0.81(2) 2.633(19) 3.0121(14) 110.5(15) 1_556 O5B H5BO O1A 0.82(3) 1.83(3) 2.6545(14) 178(3) 1_656 N1C H1CN O5B 0.87(3) 2.31(3) 2.9220(17) 128(2) . N1C H1CN O4B 0.87(3) 2.30(3) 3.0054(17) 139(2) . N1C H1CN O2A 0.87(3) 2.39(3) 2.9422(18) 122(2) 1_556 N1D H1DN O4A 0.91(3) 2.25(3) 2.9952(17) 138(2) . N1D H1DN O5A 0.91(3) 2.32(3) 2.8942(17) 121(2) . N1D H1DN O2B 0.91(3) 2.44(3) 3.0849(19) 128(2) 1_455 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 30.51 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.451 _refine_diff_density_min -0.243 _refine_diff_density_rms 0.054 _database_code_depnum_ccdc_archive 'CCDC 923466' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_publication_text #END data_sa_4pp #TrackingRef '19639_web_deposit_cif_file_0_ColinSeaton_1366368486.compiled_cifs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-phenylpyridinium saliyclate ; _chemical_name_common '4-phenylpyridinium saliyclate' _chemical_melting_point ? _chemical_formula_moiety 'C11 H10 N, C7 H5 O3' _chemical_formula_sum 'C18 H15 N O3' _chemical_formula_weight 293.31 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 P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 22.4605(5) _cell_length_b 7.1673(2) _cell_length_c 20.0652(5) _cell_angle_alpha 90.00 _cell_angle_beta 116.4380(10) _cell_angle_gamma 90.00 _cell_volume 2892.30(13) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 9877 _cell_measurement_theta_min 2.27 _cell_measurement_theta_max 29.60 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.347 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1232 _exptl_absorpt_coefficient_mu 0.092 _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 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 91018 _diffrn_reflns_av_R_equivalents 0.0415 _diffrn_reflns_av_sigmaI/netI 0.0217 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 29 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.27 _diffrn_reflns_theta_max 28.28 _reflns_number_total 7128 _reflns_number_gt 5521 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0516P)^2^+2.6590P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7128 _refine_ls_number_parameters 413 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0756 _refine_ls_R_factor_gt 0.0565 _refine_ls_wR_factor_ref 0.1654 _refine_ls_wR_factor_gt 0.1565 _refine_ls_goodness_of_fit_ref 1.167 _refine_ls_restrained_S_all 1.167 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 O1A O 0.62281(8) 0.1248(3) 0.53350(9) 0.0417(4) Uani 1 1 d . . . O2A O 0.62629(8) 0.4338(3) 0.52303(9) 0.0413(4) Uani 1 1 d . . . O3A O 0.68110(10) 0.5780(2) 0.45040(10) 0.0453(4) Uani 1 1 d . . . H3A H 0.6591(16) 0.556(5) 0.4819(18) 0.063(9) Uiso 1 1 d . . . C1A C 0.64033(10) 0.2713(3) 0.51130(11) 0.0307(5) Uani 1 1 d . . . C2A C 0.67971(9) 0.2462(3) 0.46840(10) 0.0273(4) Uani 1 1 d . . . C3A C 0.69839(10) 0.0693(3) 0.45556(12) 0.0329(5) Uani 1 1 d . . . H3AA H 0.6858 -0.0376 0.4743 0.039 Uiso 1 1 calc R . . C4A C 0.73495(11) 0.0471(4) 0.41599(14) 0.0398(6) Uani 1 1 d . . . H4A H 0.7475 -0.0739 0.4076 0.048 Uiso 1 1 calc R . . C5A C 0.75306(12) 0.2036(4) 0.38871(14) 0.0439(6) Uani 1 1 d . . . H5A H 0.7783 0.1890 0.3616 0.053 Uiso 1 1 calc R . . C6A C 0.73519(12) 0.3795(4) 0.40025(13) 0.0403(6) Uani 1 1 d . . . H6A H 0.7478 0.4852 0.3809 0.048 Uiso 1 1 calc R . . C7A C 0.69851(10) 0.4027(3) 0.44030(12) 0.0310(5) Uani 1 1 d . . . N1B N 0.56954(10) 0.1806(3) 0.62134(11) 0.0364(4) Uani 1 1 d . . . H1A H 0.5924(18) 0.170(5) 0.580(2) 0.086(12) Uiso 1 1 d . . . C1B C 0.50470(13) 0.1392(3) 0.59415(13) 0.0378(5) Uani 1 1 d . . . H1B H 0.4804 0.1059 0.5432 0.045 Uiso 1 1 calc R . . C2B C 0.47289(12) 0.1442(3) 0.63872(12) 0.0343(5) Uani 1 1 d . . . H2B H 0.4269 0.1145 0.6185 0.041 Uiso 1 1 calc R . . C3B C 0.50782(10) 0.1925(3) 0.71345(11) 0.0271(4) Uani 1 1 d . . . C4B C 0.57525(10) 0.2375(3) 0.73998(12) 0.0305(4) Uani 1 1 d . . . H4B H 0.6007 0.2736 0.7904 0.037 Uiso 1 1 calc R . . C5B C 0.60435(12) 0.2291(3) 0.69260(13) 0.0353(5) Uani 1 1 d . . . H5B H 0.6502 0.2583 0.7110 0.042 Uiso 1 1 calc R . . C6B C 0.47460(10) 0.1945(3) 0.76276(11) 0.0263(4) Uani 1 1 d . . . C7B C 0.40729(11) 0.2425(3) 0.73444(13) 0.0328(5) Uani 1 1 d . . . H7B H 0.3831 0.2775 0.6837 0.039 Uiso 1 1 calc R . . C8B C 0.37595(12) 0.2389(3) 0.78038(14) 0.0385(5) Uani 1 1 d . . . H8B H 0.3303 0.2718 0.7610 0.046 Uiso 1 1 calc R . . C9B C 0.41080(12) 0.1878(3) 0.85431(14) 0.0370(5) Uani 1 1 d . . . H9B H 0.3890 0.1848 0.8855 0.044 Uiso 1 1 calc R . . C10B C 0.47740(11) 0.1410(3) 0.88285(12) 0.0330(5) Uani 1 1 d . . . H10B H 0.5013 0.1057 0.9336 0.040 Uiso 1 1 calc R . . C11B C 0.50928(11) 0.1456(3) 0.83767(12) 0.0293(4) Uani 1 1 d . . . H11B H 0.5552 0.1151 0.8578 0.035 Uiso 1 1 calc R . . O1C O 0.87609(8) 0.6288(2) 0.90693(8) 0.0380(4) Uani 1 1 d . . . O2C O 0.87798(8) 0.9391(2) 0.90239(9) 0.0393(4) Uani 1 1 d . . . O3C O 0.82332(9) 1.1102(2) 0.78093(11) 0.0427(4) Uani 1 1 d . . . H3C H 0.8468(16) 1.081(5) 0.8289(18) 0.059(9) Uiso 1 1 d . . . C1C C 0.86123(10) 0.7819(3) 0.87184(11) 0.0284(4) Uani 1 1 d . . . C2C C 0.82136(9) 0.7744(3) 0.78894(11) 0.0259(4) Uani 1 1 d . . . C3C C 0.80100(10) 0.6070(3) 0.75166(12) 0.0308(5) Uani 1 1 d . . . H3CA H 0.8125 0.4936 0.7791 0.037 Uiso 1 1 calc R . . C4C C 0.76407(11) 0.6011(4) 0.67484(13) 0.0394(5) Uani 1 1 d . . . H4C H 0.7507 0.4848 0.6498 0.047 Uiso 1 1 calc R . . C5C C 0.74706(12) 0.7660(4) 0.63532(13) 0.0442(6) Uani 1 1 d . . . H5C H 0.7216 0.7625 0.5828 0.053 Uiso 1 1 calc R . . C6C C 0.76638(11) 0.9366(4) 0.67084(13) 0.0409(6) Uani 1 1 d . . . H6C H 0.7541 1.0490 0.6429 0.049 Uiso 1 1 calc R . . C7C C 0.80390(10) 0.9423(3) 0.74771(12) 0.0299(4) Uani 1 1 d . . . N1D N 0.92933(10) 0.6688(3) 1.04905(10) 0.0347(4) Uani 1 1 d . . . H1D H 0.9060(17) 0.661(5) 0.994(2) 0.075(10) Uiso 1 1 d . . . C1D C 0.99437(12) 0.6299(3) 1.08564(12) 0.0366(5) Uani 1 1 d . . . H1DA H 1.0185 0.6005 1.0583 0.044 Uiso 1 1 calc R . . C2D C 1.02674(11) 0.6317(3) 1.16196(12) 0.0317(5) Uani 1 1 d . . . H2D H 1.0728 0.6031 1.1870 0.038 Uiso 1 1 calc R . . C3D C 0.99206(10) 0.6754(3) 1.20271(11) 0.0251(4) Uani 1 1 d . . . C4D C 0.92442(10) 0.7173(3) 1.16302(11) 0.0294(4) Uani 1 1 d . . . H4D H 0.8991 0.7484 1.1888 0.035 Uiso 1 1 calc R . . C5D C 0.89466(11) 0.7131(3) 1.08640(12) 0.0344(5) Uani 1 1 d . . . H5D H 0.8487 0.7422 1.0596 0.041 Uiso 1 1 calc R . . C6D C 1.02632(10) 0.6778(3) 1.28534(11) 0.0251(4) Uani 1 1 d . . . C7D C 1.09358(11) 0.7241(3) 1.32300(12) 0.0310(5) Uani 1 1 d . . . H7D H 1.1175 0.7556 1.2957 0.037 Uiso 1 1 calc R . . C8D C 1.12570(11) 0.7244(3) 1.40019(12) 0.0360(5) Uani 1 1 d . . . H8D H 1.1713 0.7579 1.4255 0.043 Uiso 1 1 calc R . . C9D C 1.09159(12) 0.6761(3) 1.44062(12) 0.0357(5) Uani 1 1 d . . . H9D H 1.1140 0.6744 1.4935 0.043 Uiso 1 1 calc R . . C10D C 1.02477(11) 0.6301(3) 1.40395(12) 0.0330(5) Uani 1 1 d . . . H10D H 1.0012 0.5980 1.4316 0.040 Uiso 1 1 calc R . . C11D C 0.99236(10) 0.6312(3) 1.32665(11) 0.0275(4) Uani 1 1 d . . . H11D H 0.9465 0.5998 1.3017 0.033 Uiso 1 1 calc R . . 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 O1A 0.0420(9) 0.0511(11) 0.0392(9) 0.0107(8) 0.0244(8) 0.0059(8) O2A 0.0430(10) 0.0468(10) 0.0375(9) -0.0126(8) 0.0210(8) -0.0010(8) O3A 0.0559(11) 0.0338(9) 0.0468(10) -0.0008(8) 0.0234(9) -0.0033(8) C1A 0.0230(10) 0.0452(13) 0.0189(9) 0.0004(9) 0.0047(7) 0.0018(9) C2A 0.0198(9) 0.0370(11) 0.0201(9) -0.0017(8) 0.0043(7) 0.0007(8) C3A 0.0249(10) 0.0353(12) 0.0328(11) 0.0016(9) 0.0079(9) 0.0001(9) C4A 0.0286(11) 0.0446(14) 0.0450(13) -0.0095(11) 0.0153(10) 0.0016(10) C5A 0.0312(12) 0.0643(17) 0.0427(13) -0.0077(12) 0.0222(10) -0.0034(12) C6A 0.0317(12) 0.0525(15) 0.0382(12) 0.0021(11) 0.0169(10) -0.0101(11) C7A 0.0252(10) 0.0361(12) 0.0265(10) -0.0034(9) 0.0067(8) -0.0039(9) N1B 0.0439(11) 0.0320(10) 0.0407(11) 0.0039(8) 0.0256(9) 0.0017(8) C1B 0.0454(14) 0.0348(12) 0.0342(11) -0.0033(9) 0.0184(10) -0.0043(10) C2B 0.0341(12) 0.0333(12) 0.0334(11) -0.0002(9) 0.0132(9) -0.0055(9) C3B 0.0296(10) 0.0194(9) 0.0314(10) 0.0029(8) 0.0126(8) 0.0006(8) C4B 0.0273(10) 0.0296(11) 0.0323(10) 0.0035(9) 0.0112(8) -0.0004(8) C5B 0.0308(11) 0.0356(12) 0.0420(12) 0.0062(10) 0.0186(10) 0.0008(9) C6B 0.0274(10) 0.0188(9) 0.0318(10) -0.0001(8) 0.0125(8) -0.0035(8) C7B 0.0278(11) 0.0332(12) 0.0352(11) 0.0058(9) 0.0121(9) 0.0016(9) C8B 0.0292(11) 0.0409(13) 0.0479(13) 0.0033(11) 0.0196(10) 0.0039(10) C9B 0.0393(13) 0.0361(12) 0.0439(13) -0.0003(10) 0.0262(11) -0.0040(10) C10B 0.0361(12) 0.0323(11) 0.0296(10) -0.0018(9) 0.0137(9) -0.0058(9) C11B 0.0257(10) 0.0267(10) 0.0320(10) -0.0021(8) 0.0096(8) -0.0039(8) O1C 0.0396(9) 0.0442(10) 0.0245(7) 0.0053(7) 0.0091(7) -0.0021(7) O2C 0.0423(9) 0.0435(10) 0.0319(8) -0.0092(7) 0.0164(7) 0.0012(7) O3C 0.0523(11) 0.0338(9) 0.0447(10) 0.0027(8) 0.0239(9) 0.0011(8) C1C 0.0219(10) 0.0422(12) 0.0240(9) -0.0014(9) 0.0128(8) -0.0009(9) C2C 0.0182(9) 0.0361(11) 0.0242(9) 0.0010(8) 0.0102(7) 0.0009(8) C3C 0.0233(10) 0.0361(12) 0.0306(10) 0.0001(9) 0.0098(8) -0.0021(9) C4C 0.0310(12) 0.0491(14) 0.0333(11) -0.0090(10) 0.0100(9) -0.0081(10) C5C 0.0319(12) 0.0674(18) 0.0249(10) 0.0010(11) 0.0050(9) -0.0069(12) C6C 0.0310(12) 0.0535(15) 0.0341(12) 0.0172(11) 0.0107(10) 0.0026(11) C7C 0.0246(10) 0.0342(11) 0.0339(11) 0.0038(9) 0.0157(9) 0.0010(8) N1D 0.0409(11) 0.0323(10) 0.0237(9) 0.0019(7) 0.0078(8) -0.0017(8) C1D 0.0434(13) 0.0359(12) 0.0323(11) -0.0012(9) 0.0185(10) 0.0037(10) C2D 0.0303(11) 0.0315(11) 0.0307(10) 0.0010(9) 0.0113(9) 0.0055(9) C3D 0.0274(10) 0.0197(9) 0.0258(9) 0.0024(7) 0.0097(8) -0.0007(7) C4D 0.0272(10) 0.0302(11) 0.0288(10) 0.0029(8) 0.0108(8) -0.0012(8) C5D 0.0290(11) 0.0369(12) 0.0303(11) 0.0065(9) 0.0069(9) -0.0019(9) C6D 0.0256(10) 0.0216(9) 0.0256(9) 0.0023(7) 0.0090(8) 0.0019(7) C7D 0.0276(10) 0.0319(11) 0.0300(10) 0.0040(9) 0.0098(8) -0.0028(9) C8D 0.0283(11) 0.0387(12) 0.0321(11) 0.0029(10) 0.0052(9) -0.0062(9) C9D 0.0395(12) 0.0361(12) 0.0245(10) 0.0020(9) 0.0080(9) 0.0009(10) C10D 0.0376(12) 0.0339(12) 0.0301(10) 0.0029(9) 0.0174(9) 0.0048(9) C11D 0.0245(10) 0.0264(10) 0.0303(10) 0.0014(8) 0.0110(8) 0.0023(8) _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 O1A C1A 1.269(3) . ? O1A H1A 1.43(4) . ? O2A C1A 1.256(3) . ? O3A C7A 1.358(3) . ? O3A H3A 0.97(3) . ? C1A C2A 1.495(3) . ? C2A C3A 1.395(3) . ? C2A C7A 1.402(3) . ? C3A C4A 1.382(3) . ? C3A H3AA 0.9500 . ? C4A C5A 1.386(4) . ? C4A H4A 0.9500 . ? C5A C6A 1.373(4) . ? C5A H5A 0.9500 . ? C6A C7A 1.394(3) . ? C6A H6A 0.9500 . ? N1B C5B 1.334(3) . ? N1B C1B 1.341(3) . ? N1B H1A 1.15(4) . ? C1B C2B 1.371(3) . ? C1B H1B 0.9500 . ? C2B C3B 1.392(3) . ? C2B H2B 0.9500 . ? C3B C4B 1.401(3) . ? C3B C6B 1.481(3) . ? C4B C5B 1.374(3) . ? C4B H4B 0.9500 . ? C5B H5B 0.9500 . ? C6B C11B 1.395(3) . ? C6B C7B 1.400(3) . ? C7B C8B 1.387(3) . ? C7B H7B 0.9500 . ? C8B C9B 1.383(3) . ? C8B H8B 0.9500 . ? C9B C10B 1.384(3) . ? C9B H9B 0.9500 . ? C10B C11B 1.383(3) . ? C10B H10B 0.9500 . ? C11B H11B 0.9500 . ? O1C C1C 1.266(3) . ? O2C C1C 1.257(3) . ? O3C C7C 1.350(3) . ? O3C H3C 0.89(3) . ? C1C C2C 1.498(3) . ? C2C C3C 1.380(3) . ? C2C C7C 1.414(3) . ? C3C C4C 1.388(3) . ? C3C H3CA 0.9500 . ? C4C C5C 1.380(4) . ? C4C H4C 0.9500 . ? C5C C6C 1.384(4) . ? C5C H5C 0.9500 . ? C6C C7C 1.391(3) . ? C6C H6C 0.9500 . ? N1D C5D 1.337(3) . ? N1D C1D 1.340(3) . ? N1D H1D 1.00(3) . ? C1D C2D 1.372(3) . ? C1D H1DA 0.9500 . ? C2D C3D 1.393(3) . ? C2D H2D 0.9500 . ? C3D C4D 1.398(3) . ? C3D C6D 1.485(3) . ? C4D C5D 1.377(3) . ? C4D H4D 0.9500 . ? C5D H5D 0.9500 . ? C6D C11D 1.394(3) . ? C6D C7D 1.395(3) . ? C7D C8D 1.387(3) . ? C7D H7D 0.9500 . ? C8D C9D 1.385(3) . ? C8D H8D 0.9500 . ? C9D C10D 1.385(3) . ? C9D H9D 0.9500 . ? C10D C11D 1.389(3) . ? C10D H10D 0.9500 . ? C11D H11D 0.9500 . ? 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 C1A O1A H1A 111.0(15) . . ? C7A O3A H3A 102(2) . . ? O2A C1A O1A 123.9(2) . . ? O2A C1A C2A 118.8(2) . . ? O1A C1A C2A 117.3(2) . . ? C3A C2A C7A 118.93(19) . . ? C3A C2A C1A 121.3(2) . . ? C7A C2A C1A 119.8(2) . . ? C4A C3A C2A 121.0(2) . . ? C4A C3A H3AA 119.5 . . ? C2A C3A H3AA 119.5 . . ? C3A C4A C5A 119.2(2) . . ? C3A C4A H4A 120.4 . . ? C5A C4A H4A 120.4 . . ? C6A C5A C4A 121.1(2) . . ? C6A C5A H5A 119.4 . . ? C4A C5A H5A 119.4 . . ? C5A C6A C7A 119.9(2) . . ? C5A C6A H6A 120.0 . . ? C7A C6A H6A 120.0 . . ? O3A C7A C6A 118.7(2) . . ? O3A C7A C2A 121.5(2) . . ? C6A C7A C2A 119.8(2) . . ? C5B N1B C1B 120.4(2) . . ? C5B N1B H1A 123.2(18) . . ? C1B N1B H1A 116.4(18) . . ? N1B C1B C2B 121.0(2) . . ? N1B C1B H1B 119.5 . . ? C2B C1B H1B 119.5 . . ? C1B C2B C3B 120.1(2) . . ? C1B C2B H2B 119.9 . . ? C3B C2B H2B 119.9 . . ? C2B C3B C4B 117.5(2) . . ? C2B C3B C6B 120.81(19) . . ? C4B C3B C6B 121.65(19) . . ? C5B C4B C3B 119.6(2) . . ? C5B C4B H4B 120.2 . . ? C3B C4B H4B 120.2 . . ? N1B C5B C4B 121.4(2) . . ? N1B C5B H5B 119.3 . . ? C4B C5B H5B 119.3 . . ? C11B C6B C7B 118.9(2) . . ? C11B C6B C3B 120.77(19) . . ? C7B C6B C3B 120.35(19) . . ? C8B C7B C6B 120.1(2) . . ? C8B C7B H7B 120.0 . . ? C6B C7B H7B 120.0 . . ? C9B C8B C7B 120.3(2) . . ? C9B C8B H8B 119.8 . . ? C7B C8B H8B 119.8 . . ? C8B C9B C10B 120.0(2) . . ? C8B C9B H9B 120.0 . . ? C10B C9B H9B 120.0 . . ? C11B C10B C9B 120.2(2) . . ? C11B C10B H10B 119.9 . . ? C9B C10B H10B 119.9 . . ? C10B C11B C6B 120.5(2) . . ? C10B C11B H11B 119.7 . . ? C6B C11B H11B 119.7 . . ? C7C O3C H3C 103(2) . . ? O2C C1C O1C 123.93(19) . . ? O2C C1C C2C 118.3(2) . . ? O1C C1C C2C 117.74(19) . . ? C3C C2C C7C 118.99(18) . . ? C3C C2C C1C 121.54(19) . . ? C7C C2C C1C 119.47(19) . . ? C2C C3C C4C 121.2(2) . . ? C2C C3C H3CA 119.4 . . ? C4C C3C H3CA 119.4 . . ? C5C C4C C3C 119.2(2) . . ? C5C C4C H4C 120.4 . . ? C3C C4C H4C 120.4 . . ? C4C C5C C6C 121.2(2) . . ? C4C C5C H5C 119.4 . . ? C6C C5C H5C 119.4 . . ? C5C C6C C7C 119.6(2) . . ? C5C C6C H6C 120.2 . . ? C7C C6C H6C 120.2 . . ? O3C C7C C6C 118.5(2) . . ? O3C C7C C2C 121.70(19) . . ? C6C C7C C2C 119.8(2) . . ? C5D N1D C1D 120.48(19) . . ? C5D N1D H1D 119(2) . . ? C1D N1D H1D 120(2) . . ? N1D C1D C2D 121.1(2) . . ? N1D C1D H1DA 119.5 . . ? C2D C1D H1DA 119.5 . . ? C1D C2D C3D 120.0(2) . . ? C1D C2D H2D 120.0 . . ? C3D C2D H2D 120.0 . . ? C2D C3D C4D 117.63(19) . . ? C2D C3D C6D 120.71(18) . . ? C4D C3D C6D 121.66(19) . . ? C5D C4D C3D 119.7(2) . . ? C5D C4D H4D 120.2 . . ? C3D C4D H4D 120.2 . . ? N1D C5D C4D 121.1(2) . . ? N1D C5D H5D 119.4 . . ? C4D C5D H5D 119.5 . . ? C11D C6D C7D 118.82(19) . . ? C11D C6D C3D 120.83(18) . . ? C7D C6D C3D 120.34(19) . . ? C8D C7D C6D 120.3(2) . . ? C8D C7D H7D 119.9 . . ? C6D C7D H7D 119.9 . . ? C9D C8D C7D 120.4(2) . . ? C9D C8D H8D 119.8 . . ? C7D C8D H8D 119.8 . . ? C8D C9D C10D 119.9(2) . . ? C8D C9D H9D 120.0 . . ? C10D C9D H9D 120.0 . . ? C9D C10D C11D 119.8(2) . . ? C9D C10D H10D 120.1 . . ? C11D C10D H10D 120.1 . . ? C10D C11D C6D 120.8(2) . . ? C10D C11D H11D 119.6 . . ? C6D C11D H11D 119.6 . . ? 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 O3A H3A O2A 0.97(3) 1.59(3) 2.511(3) 156(3) . N1B H1A O1A 1.15(4) 1.43(4) 2.564(3) 170(3) . N1B H1A O2A 1.15(4) 2.50(4) 3.324(3) 127(3) . O3C H3C O2C 0.89(3) 1.67(3) 2.507(2) 155(3) . N1D H1D O1C 1.00(3) 1.58(4) 2.571(2) 172(3) . N1D H1D O2C 1.00(3) 2.59(4) 3.274(3) 126(3) . _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.237 _refine_diff_density_min -0.348 _refine_diff_density_rms 0.054 _database_code_depnum_ccdc_archive 'CCDC 923467' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_publication_text #END data_2aba_4pp_80K #TrackingRef '19639_web_deposit_cif_file_0_ColinSeaton_1366368486.compiled_cifs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2-aminobenzoic acid 4-phenylpyridine ; _chemical_name_common '2-aminobenzoic acid 4-phenylpyridine' _chemical_melting_point ? _chemical_formula_moiety 'C11 H9 N, C7 H7 N O2' _chemical_formula_sum 'C18 H16 N2 O2' _chemical_formula_weight 292.33 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 P2(1)/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 7.5367(13) _cell_length_b 10.0173(18) _cell_length_c 19.429(4) _cell_angle_alpha 90.00 _cell_angle_beta 92.881(8) _cell_angle_gamma 90.00 _cell_volume 1465.0(5) _cell_formula_units_Z 4 _cell_measurement_temperature 80(2) _cell_measurement_reflns_used 9864 _cell_measurement_theta_min 2.29 _cell_measurement_theta_max 29.87 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.54 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.35 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.325 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 616 _exptl_absorpt_coefficient_mu 0.088 _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 80(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 43508 _diffrn_reflns_av_R_equivalents 0.0530 _diffrn_reflns_av_sigmaI/netI 0.0252 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.10 _diffrn_reflns_theta_max 30.03 _reflns_number_total 3991 _reflns_number_gt 3302 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0561P)^2^+0.6460P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3991 _refine_ls_number_parameters 263 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0542 _refine_ls_R_factor_gt 0.0414 _refine_ls_wR_factor_ref 0.1154 _refine_ls_wR_factor_gt 0.1051 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 O1A O -0.04010(11) 0.99888(8) 0.61462(4) 0.01994(19) Uani 1 1 d . . . H1O H 0.038(3) 0.896(3) 0.5998(13) 0.086(8) Uiso 1 1 d . . . O2A O 0.19358(11) 1.05455(8) 0.68440(4) 0.02072(19) Uani 1 1 d . . . N1A N 0.18736(14) 1.30798(10) 0.73559(6) 0.0223(2) Uani 1 1 d . . . H1NA H 0.251(2) 1.2301(18) 0.7327(9) 0.033(4) Uiso 1 1 d . . . H2NA H 0.224(2) 1.3724(18) 0.7653(9) 0.032(4) Uiso 1 1 d . . . C1A C 0.04108(14) 1.07487(10) 0.66017(5) 0.0146(2) Uani 1 1 d . . . C2A C -0.06795(14) 1.19075(10) 0.68210(5) 0.0135(2) Uani 1 1 d . . . C3A C 0.00889(14) 1.29971(10) 0.71943(5) 0.0154(2) Uani 1 1 d . . . C4A C -0.10288(16) 1.40593(11) 0.73728(6) 0.0198(2) Uani 1 1 d . . . H4A H -0.050(2) 1.4813(16) 0.7624(8) 0.027(4) Uiso 1 1 d . . . C5A C -0.28292(17) 1.40240(12) 0.72094(6) 0.0229(2) Uani 1 1 d . . . H5A H -0.358(2) 1.4775(17) 0.7342(8) 0.030(4) Uiso 1 1 d . . . C6A C -0.35985(16) 1.29382(13) 0.68577(6) 0.0222(2) Uani 1 1 d . . . H6A H -0.484(2) 1.2929(16) 0.6739(8) 0.031(4) Uiso 1 1 d . . . C7A C -0.25156(15) 1.19027(11) 0.66638(6) 0.0172(2) Uani 1 1 d . . . H7A H -0.3050(18) 1.1151(14) 0.6404(7) 0.016(3) Uiso 1 1 d . . . N2B N 0.09922(13) 0.78210(9) 0.57790(5) 0.0187(2) Uani 1 1 d . . . C1B C 0.15447(16) 0.76816(11) 0.51399(6) 0.0210(2) Uani 1 1 d . . . H1B H 0.149(2) 0.8465(17) 0.4850(8) 0.031(4) Uiso 1 1 d . . . C2B C 0.21242(16) 0.64743(11) 0.48914(6) 0.0206(2) Uani 1 1 d . . . H2B H 0.247(2) 0.6460(18) 0.4428(9) 0.035(4) Uiso 1 1 d . . . C3B C 0.21666(14) 0.53436(10) 0.53085(5) 0.0157(2) Uani 1 1 d . . . C4B C 0.1580(2) 0.55087(12) 0.59733(6) 0.0290(3) Uani 1 1 d . . . H4B H 0.161(3) 0.479(2) 0.6315(10) 0.049(5) Uiso 1 1 d . . . C5B C 0.0992(2) 0.67438(12) 0.61827(6) 0.0280(3) Uani 1 1 d . . . H5B H 0.056(2) 0.6869(18) 0.6644(9) 0.040(5) Uiso 1 1 d . . . C6B C 0.27652(14) 0.40285(10) 0.50541(6) 0.0171(2) Uani 1 1 d . . . C7B C 0.3356(2) 0.38848(13) 0.43894(7) 0.0298(3) Uani 1 1 d . . . H7B H 0.342(2) 0.4636(19) 0.4081(10) 0.044(5) Uiso 1 1 d . . . C8B C 0.3876(2) 0.26438(14) 0.41472(7) 0.0335(3) Uani 1 1 d . . . H8B H 0.428(2) 0.261(2) 0.3692(11) 0.049(5) Uiso 1 1 d . . . C9B C 0.38261(16) 0.15338(12) 0.45678(8) 0.0280(3) Uani 1 1 d . . . H9B H 0.419(2) 0.0668(18) 0.4373(9) 0.038(4) Uiso 1 1 d . . . C10B C 0.32684(17) 0.16598(12) 0.52301(8) 0.0282(3) Uani 1 1 d . . . H10B H 0.325(2) 0.0902(19) 0.5540(9) 0.042(5) Uiso 1 1 d . . . C11B C 0.27393(15) 0.28974(12) 0.54728(7) 0.0225(2) Uani 1 1 d . . . H11B H 0.232(2) 0.2969(16) 0.5953(9) 0.031(4) 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 O1A 0.0231(4) 0.0129(4) 0.0237(4) -0.0053(3) 0.0000(3) 0.0007(3) O2A 0.0210(4) 0.0153(4) 0.0255(4) 0.0000(3) -0.0030(3) 0.0050(3) N1A 0.0217(5) 0.0167(5) 0.0282(5) -0.0059(4) -0.0027(4) -0.0022(4) C1A 0.0195(5) 0.0095(4) 0.0151(5) 0.0022(3) 0.0033(4) -0.0006(4) C2A 0.0175(5) 0.0107(4) 0.0126(4) 0.0012(3) 0.0029(4) 0.0002(4) C3A 0.0204(5) 0.0121(4) 0.0138(4) 0.0012(4) 0.0029(4) -0.0012(4) C4A 0.0294(6) 0.0130(5) 0.0174(5) -0.0021(4) 0.0064(4) 0.0006(4) C5A 0.0287(6) 0.0207(5) 0.0204(5) 0.0000(4) 0.0102(5) 0.0090(5) C6A 0.0168(5) 0.0277(6) 0.0225(5) 0.0004(5) 0.0061(4) 0.0043(4) C7A 0.0184(5) 0.0174(5) 0.0160(5) -0.0001(4) 0.0038(4) -0.0017(4) N2B 0.0221(5) 0.0123(4) 0.0214(5) -0.0033(3) -0.0011(4) 0.0011(3) C1B 0.0254(6) 0.0143(5) 0.0234(5) 0.0032(4) 0.0029(4) 0.0047(4) C2B 0.0262(6) 0.0165(5) 0.0197(5) 0.0021(4) 0.0063(4) 0.0059(4) C3B 0.0177(5) 0.0120(5) 0.0171(5) -0.0014(4) -0.0031(4) 0.0010(4) C4B 0.0578(9) 0.0122(5) 0.0173(5) -0.0005(4) 0.0043(5) 0.0010(5) C5B 0.0518(8) 0.0159(5) 0.0168(5) -0.0036(4) 0.0061(5) -0.0002(5) C6B 0.0171(5) 0.0125(5) 0.0212(5) -0.0035(4) -0.0047(4) 0.0016(4) C7B 0.0498(8) 0.0194(6) 0.0199(6) -0.0039(5) -0.0022(5) 0.0085(5) C8B 0.0474(8) 0.0266(7) 0.0261(6) -0.0123(5) -0.0029(6) 0.0095(6) C9B 0.0207(6) 0.0168(5) 0.0458(8) -0.0130(5) -0.0056(5) 0.0030(4) C10B 0.0218(6) 0.0135(5) 0.0496(8) 0.0012(5) 0.0052(5) 0.0038(4) C11B 0.0198(6) 0.0152(5) 0.0328(6) 0.0020(4) 0.0042(5) 0.0034(4) _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 O1A C1A 1.2972(13) . ? O1A H1O 1.23(3) . ? O2A C1A 1.2368(14) . ? N1A C3A 1.3683(15) . ? N1A H1NA 0.918(18) . ? N1A H2NA 0.899(18) . ? C1A C2A 1.4964(14) . ? C2A C7A 1.4021(15) . ? C2A C3A 1.4179(15) . ? C3A C4A 1.4112(15) . ? C4A C5A 1.3784(18) . ? C4A H4A 0.974(16) . ? C5A C6A 1.3951(18) . ? C5A H5A 0.982(17) . ? C6A C7A 1.3837(16) . ? C6A H6A 0.952(17) . ? C7A H7A 0.981(14) . ? N2B C5B 1.3340(15) . ? N2B C1B 1.3367(15) . ? N2B H1O 1.31(3) . ? C1B C2B 1.3812(15) . ? C1B H1B 0.966(17) . ? C2B C3B 1.3922(15) . ? C2B H2B 0.951(17) . ? C3B C4B 1.3957(16) . ? C3B C6B 1.4852(14) . ? C4B C5B 1.3823(17) . ? C4B H4B 0.98(2) . ? C5B H5B 0.978(18) . ? C6B C7B 1.3943(17) . ? C6B C11B 1.3955(16) . ? C7B C8B 1.3925(17) . ? C7B H7B 0.964(19) . ? C8B C9B 1.382(2) . ? C8B H8B 0.95(2) . ? C9B C10B 1.380(2) . ? C9B H9B 0.991(18) . ? C10B C11B 1.3919(16) . ? C10B H10B 0.969(19) . ? C11B H11B 1.003(17) . ? 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 C1A O1A H1O 115.9(12) . . ? C3A N1A H1NA 116.3(11) . . ? C3A N1A H2NA 117.1(11) . . ? H1NA N1A H2NA 120.4(15) . . ? O2A C1A O1A 124.09(10) . . ? O2A C1A C2A 122.17(9) . . ? O1A C1A C2A 113.74(9) . . ? C7A C2A C3A 119.16(9) . . ? C7A C2A C1A 119.04(9) . . ? C3A C2A C1A 121.79(10) . . ? N1A C3A C4A 119.34(10) . . ? N1A C3A C2A 122.38(10) . . ? C4A C3A C2A 118.20(10) . . ? C5A C4A C3A 121.13(10) . . ? C5A C4A H4A 120.5(9) . . ? C3A C4A H4A 118.3(9) . . ? C4A C5A C6A 120.86(10) . . ? C4A C5A H5A 119.4(10) . . ? C6A C5A H5A 119.7(10) . . ? C7A C6A C5A 118.78(11) . . ? C7A C6A H6A 120.8(10) . . ? C5A C6A H6A 120.3(10) . . ? C6A C7A C2A 121.83(10) . . ? C6A C7A H7A 118.9(8) . . ? C2A C7A H7A 119.3(8) . . ? C5B N2B C1B 118.08(10) . . ? C5B N2B H1O 120.2(12) . . ? C1B N2B H1O 121.7(12) . . ? N2B C1B C2B 122.35(10) . . ? N2B C1B H1B 116.8(10) . . ? C2B C1B H1B 120.9(10) . . ? C1B C2B C3B 120.48(10) . . ? C1B C2B H2B 116.8(11) . . ? C3B C2B H2B 122.7(11) . . ? C2B C3B C4B 116.31(10) . . ? C2B C3B C6B 121.76(10) . . ? C4B C3B C6B 121.92(10) . . ? C5B C4B C3B 119.97(11) . . ? C5B C4B H4B 117.1(11) . . ? C3B C4B H4B 122.8(11) . . ? N2B C5B C4B 122.78(11) . . ? N2B C5B H5B 116.4(11) . . ? C4B C5B H5B 120.8(11) . . ? C7B C6B C11B 118.07(10) . . ? C7B C6B C3B 121.08(10) . . ? C11B C6B C3B 120.84(10) . . ? C8B C7B C6B 120.90(12) . . ? C8B C7B H7B 117.6(11) . . ? C6B C7B H7B 121.5(11) . . ? C9B C8B C7B 120.15(13) . . ? C9B C8B H8B 122.5(12) . . ? C7B C8B H8B 117.4(12) . . ? C10B C9B C8B 119.78(11) . . ? C10B C9B H9B 122.7(10) . . ? C8B C9B H9B 117.5(10) . . ? C9B C10B C11B 120.23(12) . . ? C9B C10B H10B 121.4(11) . . ? C11B C10B H10B 118.4(11) . . ? C10B C11B C6B 120.87(12) . . ? C10B C11B H11B 119.2(9) . . ? C6B C11B H11B 119.9(9) . . ? 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 O1A H1O N2B 1.23(3) 1.31(3) 2.5302(12) 171(2) . N1A H1NA O2A 0.918(18) 2.030(18) 2.7279(14) 131.7(14) . N1A H2NA O2A 0.899(18) 2.148(18) 3.0303(14) 166.9(15) 2_556 _diffrn_measured_fraction_theta_max 0.930 _diffrn_reflns_theta_full 28.50 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.373 _refine_diff_density_min -0.306 _refine_diff_density_rms 0.048 _database_code_depnum_ccdc_archive 'CCDC 923468' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_publication_text #END data_2aba_4pp_120k #TrackingRef '19639_web_deposit_cif_file_0_ColinSeaton_1366368486.compiled_cifs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2-aminobenzoic acid 4-phenylpyridine ; _chemical_name_common '2-aminobenzoic acid 4-phenylpyridine' _chemical_melting_point ? _chemical_formula_moiety 'C11 H9 N, C7 H7 N O2' _chemical_formula_sum 'C18 H16 N2 O2' _chemical_formula_weight 292.33 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 P2(1)/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 7.5472(9) _cell_length_b 10.0169(12) _cell_length_c 19.516(3) _cell_angle_alpha 90.00 _cell_angle_beta 92.845(6) _cell_angle_gamma 90.00 _cell_volume 1473.6(3) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 9773 _cell_measurement_theta_min 2.29 _cell_measurement_theta_max 29.79 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.54 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.35 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.318 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 616 _exptl_absorpt_coefficient_mu 0.087 _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 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 44725 _diffrn_reflns_av_R_equivalents 0.0518 _diffrn_reflns_av_sigmaI/netI 0.0244 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 29.93 _reflns_number_total 4016 _reflns_number_gt 3144 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0665P)^2^+0.2469P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4016 _refine_ls_number_parameters 263 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0564 _refine_ls_R_factor_gt 0.0421 _refine_ls_wR_factor_ref 0.1192 _refine_ls_wR_factor_gt 0.1116 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 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 O1A O 1.03921(10) 0.00089(8) 0.38473(4) 0.0283(2) Uani 1 1 d . . . H1O H 0.968(3) 0.100(2) 0.3988(11) 0.088(7) Uiso 1 1 d . . . O2A O 0.80616(10) -0.05531(8) 0.31579(4) 0.0290(2) Uani 1 1 d . . . N1A N 0.81277(14) -0.30826(10) 0.26437(6) 0.0311(2) Uani 1 1 d . . . H1NA H 0.777(2) -0.3735(17) 0.2353(8) 0.041(4) Uiso 1 1 d . . . H2NA H 0.748(2) -0.2295(16) 0.2679(8) 0.039(4) Uiso 1 1 d . . . C1A C 0.95827(14) -0.07559(10) 0.33966(5) 0.0202(2) Uani 1 1 d . . . C2A C 1.06710(13) -0.19132(9) 0.31791(5) 0.0187(2) Uani 1 1 d . . . C3A C 0.99068(14) -0.29997(10) 0.28059(5) 0.0214(2) Uani 1 1 d . . . C4A C 1.10231(16) -0.40596(11) 0.26274(6) 0.0279(3) Uani 1 1 d . . . H4A H 1.0483(18) -0.4810(14) 0.2378(7) 0.033(4) Uiso 1 1 d . . . C5A C 1.28136(17) -0.40251(12) 0.27909(6) 0.0324(3) Uani 1 1 d . . . H5A H 1.357(2) -0.4784(16) 0.2657(8) 0.048(4) Uiso 1 1 d . . . C6A C 1.35806(16) -0.29443(12) 0.31437(6) 0.0307(3) Uani 1 1 d . . . H6A H 1.483(2) -0.2936(14) 0.3261(8) 0.037(4) Uiso 1 1 d . . . C7A C 1.24997(15) -0.19096(11) 0.33370(5) 0.0240(2) Uani 1 1 d . . . H7A H 1.3012(16) -0.1168(13) 0.3610(6) 0.025(3) Uiso 1 1 d . . . N1B N 0.89935(13) 0.21783(9) 0.42167(5) 0.0264(2) Uani 1 1 d . . . C1B C 0.84486(15) 0.23162(11) 0.48519(6) 0.0283(3) Uani 1 1 d . . . H1B H 0.8481(19) 0.1529(16) 0.5141(8) 0.041(4) Uiso 1 1 d . . . C2B C 0.78737(15) 0.35213(11) 0.51028(6) 0.0275(2) Uani 1 1 d . . . H2B H 0.753(2) 0.3540(17) 0.5562(8) 0.047(4) Uiso 1 1 d . . . C3B C 0.78308(14) 0.46533(10) 0.46916(5) 0.0218(2) Uani 1 1 d . . . C4B C 0.8411(2) 0.44921(12) 0.40309(6) 0.0388(3) Uani 1 1 d . . . H4B H 0.836(2) 0.5199(18) 0.3695(9) 0.060(5) Uiso 1 1 d . . . C5B C 0.8996(2) 0.32583(12) 0.38186(6) 0.0385(3) Uani 1 1 d . . . H5B H 0.941(2) 0.3129(17) 0.3359(9) 0.055(5) Uiso 1 1 d . . . C6B C 0.72371(14) 0.59687(10) 0.49480(6) 0.0237(2) Uani 1 1 d . . . C7B C 0.6661(2) 0.61101(13) 0.56104(7) 0.0402(3) Uani 1 1 d . . . H7B H 0.662(2) 0.5355(19) 0.5914(9) 0.057(5) Uiso 1 1 d . . . C8B C 0.6143(2) 0.73505(15) 0.58542(8) 0.0456(4) Uani 1 1 d . . . H8B H 0.570(2) 0.734(2) 0.6309(11) 0.068(5) Uiso 1 1 d . . . C9B C 0.61832(16) 0.84581(12) 0.54354(8) 0.0393(3) Uani 1 1 d . . . H9B H 0.580(2) 0.9323(17) 0.5637(9) 0.051(4) Uiso 1 1 d . . . C10B C 0.67252(17) 0.83348(12) 0.47766(8) 0.0386(3) Uani 1 1 d . . . H10B H 0.675(2) 0.9103(19) 0.4468(9) 0.059(5) Uiso 1 1 d . . . C11B C 0.72521(15) 0.70992(11) 0.45326(7) 0.0307(3) Uani 1 1 d . . . H11B H 0.766(2) 0.7019(15) 0.4053(9) 0.044(4) 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 O1A 0.0319(4) 0.0181(4) 0.0345(4) -0.0079(3) -0.0003(3) 0.0015(3) O2A 0.0288(4) 0.0214(4) 0.0363(4) -0.0004(3) -0.0039(3) 0.0075(3) N1A 0.0297(5) 0.0237(5) 0.0395(6) -0.0087(4) -0.0028(4) -0.0027(4) C1A 0.0257(5) 0.0135(4) 0.0218(5) 0.0032(3) 0.0040(4) -0.0005(4) C2A 0.0239(5) 0.0146(4) 0.0180(4) 0.0021(3) 0.0046(4) 0.0001(4) C3A 0.0281(6) 0.0168(4) 0.0196(5) 0.0015(4) 0.0050(4) -0.0013(4) C4A 0.0407(7) 0.0189(5) 0.0249(5) -0.0033(4) 0.0087(5) 0.0009(4) C5A 0.0402(7) 0.0293(6) 0.0288(6) -0.0009(5) 0.0138(5) 0.0123(5) C6A 0.0234(6) 0.0380(6) 0.0313(6) 0.0003(5) 0.0085(5) 0.0062(5) C7A 0.0254(6) 0.0244(5) 0.0226(5) 0.0001(4) 0.0059(4) -0.0019(4) N1B 0.0308(5) 0.0172(4) 0.0311(5) -0.0051(3) -0.0005(4) 0.0013(4) C1B 0.0332(6) 0.0188(5) 0.0332(6) 0.0035(4) 0.0038(5) 0.0048(4) C2B 0.0342(6) 0.0219(5) 0.0272(6) 0.0022(4) 0.0078(5) 0.0056(4) C3B 0.0236(5) 0.0167(5) 0.0245(5) -0.0025(4) -0.0035(4) 0.0013(4) C4B 0.0744(10) 0.0177(5) 0.0248(6) -0.0002(4) 0.0063(6) 0.0020(6) C5B 0.0693(9) 0.0222(6) 0.0245(6) -0.0054(4) 0.0091(6) 0.0002(5) C6B 0.0229(5) 0.0178(5) 0.0299(5) -0.0048(4) -0.0054(4) 0.0018(4) C7B 0.0633(9) 0.0274(6) 0.0293(6) -0.0065(5) -0.0023(6) 0.0110(6) C8B 0.0598(9) 0.0382(7) 0.0381(7) -0.0184(6) -0.0038(6) 0.0127(6) C9B 0.0284(6) 0.0232(6) 0.0652(9) -0.0175(6) -0.0083(6) 0.0046(5) C10B 0.0293(6) 0.0187(5) 0.0681(9) -0.0002(6) 0.0062(6) 0.0050(5) C11B 0.0262(6) 0.0207(5) 0.0456(7) 0.0020(5) 0.0047(5) 0.0043(4) _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 O1A C1A 1.2963(13) . ? O1A H1O 1.17(2) . ? O2A C1A 1.2341(13) . ? N1A C3A 1.3667(15) . ? N1A H1NA 0.898(16) . ? N1A H2NA 0.932(16) . ? C1A C2A 1.4944(13) . ? C2A C7A 1.3992(15) . ? C2A C3A 1.4163(14) . ? C3A C4A 1.4097(15) . ? C4A C5A 1.3735(18) . ? C4A H4A 0.973(15) . ? C5A C6A 1.3934(18) . ? C5A H5A 0.992(16) . ? C6A C7A 1.3829(16) . ? C6A H6A 0.959(15) . ? C7A H7A 0.982(13) . ? N1B C5B 1.3318(15) . ? N1B C1B 1.3324(15) . ? N1B H1O 1.37(2) . ? C1B C2B 1.3807(15) . ? C1B H1B 0.969(16) . ? C2B C3B 1.3887(15) . ? C2B H2B 0.945(16) . ? C3B C4B 1.3916(16) . ? C3B C6B 1.4865(14) . ? C4B C5B 1.3826(17) . ? C4B H4B 0.965(19) . ? C5B H5B 0.975(18) . ? C6B C7B 1.3914(17) . ? C6B C11B 1.3931(16) . ? C7B C8B 1.3934(18) . ? C7B H7B 0.962(19) . ? C8B C9B 1.379(2) . ? C8B H8B 0.96(2) . ? C9B C10B 1.374(2) . ? C9B H9B 1.000(17) . ? C10B C11B 1.3913(16) . ? C10B H10B 0.977(18) . ? C11B H11B 1.003(17) . ? 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 C1A O1A H1O 117.1(11) . . ? C3A N1A H1NA 116.8(10) . . ? C3A N1A H2NA 116.3(9) . . ? H1NA N1A H2NA 121.5(14) . . ? O2A C1A O1A 123.85(9) . . ? O2A C1A C2A 122.32(9) . . ? O1A C1A C2A 113.83(9) . . ? C7A C2A C3A 119.16(9) . . ? C7A C2A C1A 119.05(9) . . ? C3A C2A C1A 121.78(9) . . ? N1A C3A C4A 119.30(10) . . ? N1A C3A C2A 122.42(9) . . ? C4A C3A C2A 118.21(10) . . ? C5A C4A C3A 121.12(10) . . ? C5A C4A H4A 121.2(8) . . ? C3A C4A H4A 117.7(8) . . ? C4A C5A C6A 120.94(10) . . ? C4A C5A H5A 119.3(9) . . ? C6A C5A H5A 119.8(9) . . ? C7A C6A C5A 118.75(11) . . ? C7A C6A H6A 121.0(9) . . ? C5A C6A H6A 120.3(9) . . ? C6A C7A C2A 121.79(10) . . ? C6A C7A H7A 119.6(7) . . ? C2A C7A H7A 118.6(7) . . ? C5B N1B C1B 117.89(10) . . ? C5B N1B H1O 119.8(9) . . ? C1B N1B H1O 122.1(9) . . ? N1B C1B C2B 122.52(10) . . ? N1B C1B H1B 117.2(9) . . ? C2B C1B H1B 120.3(9) . . ? C1B C2B C3B 120.51(10) . . ? C1B C2B H2B 117.4(10) . . ? C3B C2B H2B 122.1(10) . . ? C2B C3B C4B 116.19(10) . . ? C2B C3B C6B 121.87(10) . . ? C4B C3B C6B 121.93(10) . . ? C5B C4B C3B 120.07(11) . . ? C5B C4B H4B 117.0(11) . . ? C3B C4B H4B 122.8(11) . . ? N1B C5B C4B 122.80(11) . . ? N1B C5B H5B 116.0(10) . . ? C4B C5B H5B 121.1(10) . . ? C7B C6B C11B 118.03(10) . . ? C7B C6B C3B 121.09(10) . . ? C11B C6B C3B 120.88(10) . . ? C6B C7B C8B 120.93(13) . . ? C6B C7B H7B 120.8(11) . . ? C8B C7B H7B 118.3(11) . . ? C9B C8B C7B 120.00(14) . . ? C9B C8B H8B 124.7(12) . . ? C7B C8B H8B 115.1(12) . . ? C10B C9B C8B 119.91(11) . . ? C10B C9B H9B 123.5(10) . . ? C8B C9B H9B 116.6(10) . . ? C9B C10B C11B 120.25(13) . . ? C9B C10B H10B 121.4(10) . . ? C11B C10B H10B 118.4(10) . . ? C10B C11B C6B 120.87(12) . . ? C10B C11B H11B 119.8(9) . . ? C6B C11B H11B 119.3(9) . . ? 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 O1A H1O N1B 1.17(2) 1.37(2) 2.5361(12) 173(2) . N1A H2NA O2A 0.932(16) 2.017(16) 2.7266(13) 131.7(12) . N1A H1NA O2A 0.898(16) 2.155(17) 3.0394(13) 168.1(14) 2_645 _diffrn_measured_fraction_theta_max 0.941 _diffrn_reflns_theta_full 28.50 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.325 _refine_diff_density_min -0.281 _refine_diff_density_rms 0.044 _database_code_depnum_ccdc_archive 'CCDC 923469' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_publication_text #END data_2aba_4pp_150K #TrackingRef '19639_web_deposit_cif_file_0_ColinSeaton_1366368486.compiled_cifs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2-aminobenzoic acid 4-phenylpyridine ; _chemical_name_common '2-aminobenzoic acid 4-phenylpyridine' _chemical_melting_point ? _chemical_formula_moiety 'C11 H9 N, C7 H7 N O2' _chemical_formula_sum 'C18 H16 N2 O2' _chemical_formula_weight 292.33 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 P2(1)/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 7.5570(7) _cell_length_b 10.0088(10) _cell_length_c 19.597(2) _cell_angle_alpha 90.00 _cell_angle_beta 92.793(5) _cell_angle_gamma 90.00 _cell_volume 1480.5(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 9075 _cell_measurement_theta_min 2.29 _cell_measurement_theta_max 29.72 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.54 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.35 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.312 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 616 _exptl_absorpt_coefficient_mu 0.087 _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 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 44975 _diffrn_reflns_av_R_equivalents 0.0369 _diffrn_reflns_av_sigmaI/netI 0.0223 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.08 _diffrn_reflns_theta_max 29.92 _reflns_number_total 4039 _reflns_number_gt 3028 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0678P)^2^+0.2253P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4039 _refine_ls_number_parameters 263 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0621 _refine_ls_R_factor_gt 0.0432 _refine_ls_wR_factor_ref 0.1232 _refine_ls_wR_factor_gt 0.1133 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 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 O1A O 0.46164(11) 0.49940(8) 0.61582(4) 0.0346(2) Uani 1 1 d . . . H1O H 0.531(3) 0.402(2) 0.6027(11) 0.095(7) Uiso 1 1 d . . . O2A O 0.69410(11) 0.55594(8) 0.68402(4) 0.0354(2) Uani 1 1 d . . . N1A N 0.68704(14) 0.80859(11) 0.73554(6) 0.0378(3) Uani 1 1 d . . . H1NA H 0.724(2) 0.8727(17) 0.7650(8) 0.048(4) Uiso 1 1 d . . . H2NA H 0.751(2) 0.7291(17) 0.7323(8) 0.048(4) Uiso 1 1 d . . . C1A C 0.54236(14) 0.57609(10) 0.66047(5) 0.0242(2) Uani 1 1 d . . . C2A C 0.43363(14) 0.69182(10) 0.68210(5) 0.0224(2) Uani 1 1 d . . . C3A C 0.50970(15) 0.80030(10) 0.71933(5) 0.0254(2) Uani 1 1 d . . . C4A C 0.39818(17) 0.90607(12) 0.73724(6) 0.0336(3) Uani 1 1 d . . . H4A H 0.4517(19) 0.9815(15) 0.7629(8) 0.042(4) Uiso 1 1 d . . . C5A C 0.21987(18) 0.90264(13) 0.72083(7) 0.0392(3) Uani 1 1 d . . . H5A H 0.145(2) 0.9781(17) 0.7340(9) 0.054(4) Uiso 1 1 d . . . C6A C 0.14360(17) 0.79483(14) 0.68553(7) 0.0372(3) Uani 1 1 d . . . H6A H 0.020(2) 0.7946(15) 0.6743(8) 0.044(4) Uiso 1 1 d . . . C7A C 0.25131(15) 0.69147(12) 0.66623(6) 0.0288(2) Uani 1 1 d . . . H7A H 0.2005(16) 0.6174(13) 0.6390(6) 0.027(3) Uiso 1 1 d . . . N1B N 0.60188(13) 0.28229(9) 0.57862(5) 0.0322(2) Uani 1 1 d . . . C1B C 0.65553(16) 0.26857(12) 0.51542(7) 0.0338(3) Uani 1 1 d . . . H1B H 0.650(2) 0.3462(16) 0.4867(8) 0.050(4) Uiso 1 1 d . . . C2B C 0.71244(16) 0.14821(12) 0.49015(6) 0.0326(3) Uani 1 1 d . . . H2B H 0.746(2) 0.1468(17) 0.4440(8) 0.052(4) Uiso 1 1 d . . . C3B C 0.71726(14) 0.03489(10) 0.53085(6) 0.0258(2) Uani 1 1 d . . . C4B C 0.6595(2) 0.05074(13) 0.59660(7) 0.0464(4) Uani 1 1 d . . . H4B H 0.665(2) -0.020(2) 0.6299(10) 0.072(6) Uiso 1 1 d . . . C5B C 0.6018(2) 0.17400(13) 0.61790(7) 0.0461(4) Uani 1 1 d . . . H5B H 0.559(2) 0.1858(17) 0.6632(9) 0.061(5) Uiso 1 1 d . . . C6B C 0.77609(14) -0.09666(11) 0.50501(6) 0.0283(2) Uani 1 1 d . . . C7B C 0.8327(2) -0.11050(14) 0.43904(7) 0.0478(4) Uani 1 1 d . . . H7B H 0.837(2) -0.035(2) 0.4087(10) 0.067(5) Uiso 1 1 d . . . C8B C 0.8842(2) -0.23468(16) 0.41458(9) 0.0550(4) Uani 1 1 d . . . H8B H 0.929(2) -0.233(2) 0.3702(11) 0.073(6) Uiso 1 1 d . . . C9B C 0.88103(18) -0.34512(13) 0.45630(9) 0.0477(4) Uani 1 1 d . . . H9B H 0.920(2) -0.4307(18) 0.4358(9) 0.057(5) Uiso 1 1 d . . . C10B C 0.82796(18) -0.33313(13) 0.52185(9) 0.0467(4) Uani 1 1 d . . . H10B H 0.827(2) -0.411(2) 0.5522(10) 0.074(6) Uiso 1 1 d . . . C11B C 0.77568(16) -0.20956(12) 0.54629(7) 0.0369(3) Uani 1 1 d . . . H11B H 0.736(2) -0.2016(16) 0.5940(9) 0.052(4) 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 O1A 0.0386(5) 0.0228(4) 0.0422(5) -0.0103(3) -0.0011(4) 0.0019(3) O2A 0.0354(5) 0.0259(4) 0.0443(5) -0.0008(3) -0.0054(4) 0.0092(3) N1A 0.0356(6) 0.0298(5) 0.0472(6) -0.0109(5) -0.0047(5) -0.0035(4) C1A 0.0304(6) 0.0166(4) 0.0260(5) 0.0032(4) 0.0036(4) -0.0005(4) C2A 0.0287(5) 0.0177(5) 0.0211(5) 0.0027(4) 0.0048(4) 0.0002(4) C3A 0.0339(6) 0.0202(5) 0.0225(5) 0.0012(4) 0.0047(4) -0.0014(4) C4A 0.0484(7) 0.0235(5) 0.0297(6) -0.0047(4) 0.0099(5) 0.0015(5) C5A 0.0479(8) 0.0360(6) 0.0351(6) -0.0022(5) 0.0161(5) 0.0150(6) C6A 0.0282(6) 0.0471(7) 0.0371(6) 0.0002(5) 0.0096(5) 0.0077(5) C7A 0.0297(6) 0.0302(6) 0.0269(5) -0.0002(4) 0.0061(4) -0.0026(4) N1B 0.0378(6) 0.0210(5) 0.0375(5) -0.0063(4) -0.0007(4) 0.0017(4) C1B 0.0397(7) 0.0219(5) 0.0400(7) 0.0038(5) 0.0039(5) 0.0050(5) C2B 0.0403(7) 0.0260(6) 0.0321(6) 0.0025(4) 0.0086(5) 0.0062(5) C3B 0.0279(5) 0.0198(5) 0.0293(5) -0.0030(4) -0.0041(4) 0.0013(4) C4B 0.0887(11) 0.0215(6) 0.0293(6) 0.0001(5) 0.0060(6) 0.0023(6) C5B 0.0823(11) 0.0279(6) 0.0287(6) -0.0067(5) 0.0098(6) 0.0008(6) C6B 0.0271(6) 0.0211(5) 0.0360(6) -0.0065(4) -0.0066(4) 0.0023(4) C7B 0.0742(10) 0.0334(7) 0.0352(7) -0.0088(5) -0.0034(7) 0.0127(6) C8B 0.0703(10) 0.0472(9) 0.0466(8) -0.0233(7) -0.0052(7) 0.0154(7) C9B 0.0346(7) 0.0283(6) 0.0790(11) -0.0219(7) -0.0104(7) 0.0060(5) C10B 0.0360(7) 0.0233(6) 0.0812(11) -0.0013(6) 0.0060(7) 0.0062(5) C11B 0.0321(6) 0.0248(6) 0.0540(8) 0.0022(5) 0.0042(6) 0.0051(4) _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 O1A C1A 1.2941(13) . ? O1A H1O 1.14(2) . ? O2A C1A 1.2317(13) . ? N1A C3A 1.3647(16) . ? N1A H1NA 0.898(17) . ? N1A H2NA 0.935(17) . ? C1A C2A 1.4936(14) . ? C2A C7A 1.3976(15) . ? C2A C3A 1.4145(15) . ? C3A C4A 1.4081(15) . ? C4A C5A 1.3704(19) . ? C4A H4A 0.983(16) . ? C5A C6A 1.392(2) . ? C5A H5A 0.986(17) . ? C6A C7A 1.3805(17) . ? C6A H6A 0.951(16) . ? C7A H7A 0.980(13) . ? N1B C1B 1.3289(16) . ? N1B C5B 1.3294(17) . ? N1B H1O 1.41(2) . ? C1B C2B 1.3792(16) . ? C1B H1B 0.960(16) . ? C2B C3B 1.3861(16) . ? C2B H2B 0.951(16) . ? C3B C4B 1.3895(17) . ? C3B C6B 1.4865(14) . ? C4B C5B 1.3798(18) . ? C4B H4B 0.96(2) . ? C5B H5B 0.967(18) . ? C6B C7B 1.3884(19) . ? C6B C11B 1.3898(17) . ? C7B C8B 1.3942(19) . ? C7B H7B 0.96(2) . ? C8B C9B 1.376(2) . ? C8B H8B 0.95(2) . ? C9B C10B 1.370(2) . ? C9B H9B 0.997(18) . ? C10B C11B 1.3906(17) . ? C10B H10B 0.98(2) . ? C11B H11B 0.997(17) . ? 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 C1A O1A H1O 116.9(11) . . ? C3A N1A H1NA 117.4(10) . . ? C3A N1A H2NA 115.9(10) . . ? H1NA N1A H2NA 120.5(14) . . ? O2A C1A O1A 123.76(10) . . ? O2A C1A C2A 122.39(9) . . ? O1A C1A C2A 113.84(9) . . ? C7A C2A C3A 119.22(10) . . ? C7A C2A C1A 119.01(9) . . ? C3A C2A C1A 121.76(10) . . ? N1A C3A C4A 119.29(10) . . ? N1A C3A C2A 122.45(10) . . ? C4A C3A C2A 118.19(10) . . ? C5A C4A C3A 121.08(11) . . ? C5A C4A H4A 120.9(9) . . ? C3A C4A H4A 118.0(9) . . ? C4A C5A C6A 120.98(11) . . ? C4A C5A H5A 119.4(10) . . ? C6A C5A H5A 119.7(10) . . ? C7A C6A C5A 118.80(12) . . ? C7A C6A H6A 121.4(9) . . ? C5A C6A H6A 119.8(9) . . ? C6A C7A C2A 121.68(11) . . ? C6A C7A H7A 119.7(7) . . ? C2A C7A H7A 118.6(7) . . ? C1B N1B C5B 117.65(10) . . ? C1B N1B H1O 122.6(9) . . ? C5B N1B H1O 119.4(9) . . ? N1B C1B C2B 122.66(11) . . ? N1B C1B H1B 117.2(10) . . ? C2B C1B H1B 120.1(10) . . ? C1B C2B C3B 120.53(11) . . ? C1B C2B H2B 117.2(10) . . ? C3B C2B H2B 122.3(10) . . ? C2B C3B C4B 116.08(10) . . ? C2B C3B C6B 121.91(10) . . ? C4B C3B C6B 121.99(10) . . ? C5B C4B C3B 120.05(12) . . ? C5B C4B H4B 117.0(11) . . ? C3B C4B H4B 122.8(11) . . ? N1B C5B C4B 123.01(12) . . ? N1B C5B H5B 116.2(10) . . ? C4B C5B H5B 120.8(10) . . ? C7B C6B C11B 118.06(11) . . ? C7B C6B C3B 121.10(11) . . ? C11B C6B C3B 120.84(11) . . ? C6B C7B C8B 120.85(14) . . ? C6B C7B H7B 121.3(11) . . ? C8B C7B H7B 117.9(11) . . ? C9B C8B C7B 119.92(15) . . ? C9B C8B H8B 125.0(13) . . ? C7B C8B H8B 114.9(13) . . ? C10B C9B C8B 120.09(12) . . ? C10B C9B H9B 124.0(10) . . ? C8B C9B H9B 115.9(10) . . ? C9B C10B C11B 120.14(14) . . ? C9B C10B H10B 120.7(11) . . ? C11B C10B H10B 119.2(11) . . ? C6B C11B C10B 120.92(13) . . ? C6B C11B H11B 119.3(9) . . ? C10B C11B H11B 119.8(9) . . ? 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 O1A H1O N1B 1.14(2) 1.41(2) 2.5400(12) 172(2) . N1A H2NA O2A 0.935(17) 2.011(17) 2.7244(14) 131.8(13) . N1A H1NA O2A 0.898(17) 2.165(17) 3.0467(14) 167.0(14) 2_656 _diffrn_measured_fraction_theta_max 0.941 _diffrn_reflns_theta_full 28.50 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.289 _refine_diff_density_min -0.274 _refine_diff_density_rms 0.042 _database_code_depnum_ccdc_archive 'CCDC 923470' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_publication_text #END data_2aba_4pp_173K #TrackingRef '19639_web_deposit_cif_file_0_ColinSeaton_1366368486.compiled_cifs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2-aminobenzoic acid 4-phenylpyridine ; _chemical_name_common '2-aminobenzoic acid 4-phenylpyridine' _chemical_melting_point ? _chemical_formula_moiety 'C11 H9 N, C7 H7 N O2' _chemical_formula_sum 'C18 H16 N2 O2' _chemical_formula_weight 292.33 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 P2(1)/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 7.5656(6) _cell_length_b 10.0044(9) _cell_length_c 19.6836(18) _cell_angle_alpha 90.00 _cell_angle_beta 92.755(4) _cell_angle_gamma 90.00 _cell_volume 1488.1(2) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 9934 _cell_measurement_theta_min 2.28 _cell_measurement_theta_max 29.75 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.54 _exptl_crystal_size_mid 0.41 _exptl_crystal_size_min 0.29 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.305 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 616 _exptl_absorpt_coefficient_mu 0.086 _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 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 45428 _diffrn_reflns_av_R_equivalents 0.0273 _diffrn_reflns_av_sigmaI/netI 0.0132 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 2.28 _diffrn_reflns_theta_max 29.88 _reflns_number_total 4163 _reflns_number_gt 3423 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0696P)^2^+0.4640P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4163 _refine_ls_number_parameters 263 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0587 _refine_ls_R_factor_gt 0.0474 _refine_ls_wR_factor_ref 0.1380 _refine_ls_wR_factor_gt 0.1262 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 O1A O -0.03769(12) -0.49968(9) 0.11618(5) 0.0404(2) Uani 1 1 d . . . H1OA H 0.032(3) -0.406(3) 0.1039(12) 0.094(7) Uiso 1 1 d . . . O2A O 0.19459(12) -0.55660(9) 0.18387(5) 0.0415(2) Uani 1 1 d . . . N1A N 0.18724(16) -0.80896(13) 0.23545(7) 0.0442(3) Uani 1 1 d . . . H1NA H 0.224(2) -0.8728(19) 0.2636(9) 0.051(5) Uiso 1 1 d . . . H2NA H 0.250(2) -0.728(2) 0.2321(9) 0.055(5) Uiso 1 1 d . . . C1A C -0.06548(14) -0.69215(10) 0.18207(5) 0.0258(2) Uani 1 1 d . . . C2A C 0.01026(16) -0.80059(11) 0.21931(6) 0.0298(2) Uani 1 1 d . . . C3A C -0.10139(19) -0.90634(13) 0.23724(7) 0.0391(3) Uani 1 1 d . . . H3A H -0.046(2) -0.9816(19) 0.2630(9) 0.053(5) Uiso 1 1 d . . . C4A C -0.2791(2) -0.90304(15) 0.22083(7) 0.0457(3) Uani 1 1 d . . . H4A H -0.355(3) -0.978(2) 0.2345(10) 0.064(5) Uiso 1 1 d . . . C5A C -0.35529(18) -0.79540(16) 0.18552(7) 0.0436(3) Uani 1 1 d . . . H5A H -0.479(3) -0.7937(18) 0.1745(9) 0.057(5) Uiso 1 1 d . . . C6A C -0.24769(16) -0.69186(13) 0.16608(6) 0.0334(3) Uani 1 1 d . . . H6A H -0.2996(18) -0.6190(15) 0.1393(7) 0.032(3) Uiso 1 1 d . . . C7A C 0.04306(15) -0.57651(10) 0.16057(6) 0.0288(2) Uani 1 1 d . . . N1B N 0.10284(15) -0.28251(10) 0.07892(6) 0.0376(2) Uani 1 1 d . . . C1B C 0.15562(18) -0.26893(12) 0.01576(7) 0.0392(3) Uani 1 1 d . . . H1B H 0.150(2) -0.348(2) -0.0123(10) 0.058(5) Uiso 1 1 d . . . C2B C 0.21231(18) -0.14855(12) -0.00973(7) 0.0371(3) Uani 1 1 d . . . H2B H 0.244(2) -0.147(2) -0.0569(10) 0.063(5) Uiso 1 1 d . . . C3B C 0.21744(15) -0.03499(11) 0.03077(6) 0.0302(2) Uani 1 1 d . . . C4B C 0.1602(3) -0.05066(14) 0.09645(7) 0.0533(4) Uani 1 1 d . . . H4B H 0.165(3) 0.021(2) 0.1299(11) 0.079(7) Uiso 1 1 d . . . C5B C 0.1026(3) -0.17413(15) 0.11784(7) 0.0536(4) Uani 1 1 d . . . H5B H 0.061(3) -0.185(2) 0.1632(11) 0.075(6) Uiso 1 1 d . . . C6B C 0.27606(15) 0.09632(11) 0.00493(6) 0.0330(3) Uani 1 1 d . . . C7B C 0.3318(3) 0.11003(16) -0.06107(8) 0.0555(4) Uani 1 1 d . . . H7B H 0.332(3) 0.036(2) -0.0914(11) 0.073(6) Uiso 1 1 d . . . C8B C 0.3832(3) 0.23442(19) -0.08542(10) 0.0639(5) Uani 1 1 d . . . H8B H 0.425(3) 0.231(3) -0.1292(13) 0.090(7) Uiso 1 1 d . . . C9B C 0.3804(2) 0.34500(15) -0.04392(10) 0.0567(5) Uani 1 1 d . . . H9B H 0.420(3) 0.431(2) -0.0625(11) 0.073(6) Uiso 1 1 d . . . C10B C 0.3284(2) 0.33289(14) 0.02160(11) 0.0548(4) Uani 1 1 d . . . H10B H 0.326(3) 0.412(3) 0.0510(11) 0.084(7) Uiso 1 1 d . . . C11B C 0.27634(18) 0.20944(13) 0.04607(8) 0.0427(3) Uani 1 1 d . . . H11B H 0.235(3) 0.2015(19) 0.0944(10) 0.063(5) 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 O1A 0.0445(5) 0.0275(4) 0.0487(5) 0.0122(4) -0.0019(4) -0.0023(3) O2A 0.0418(5) 0.0311(4) 0.0508(5) 0.0018(4) -0.0070(4) -0.0109(4) N1A 0.0420(6) 0.0353(6) 0.0545(7) 0.0121(5) -0.0067(5) 0.0046(5) C1A 0.0323(5) 0.0208(4) 0.0247(5) -0.0024(4) 0.0044(4) -0.0001(4) C2A 0.0387(6) 0.0240(5) 0.0270(5) -0.0005(4) 0.0044(4) 0.0012(4) C3A 0.0554(8) 0.0281(6) 0.0346(6) 0.0056(5) 0.0111(5) -0.0026(5) C4A 0.0550(8) 0.0432(7) 0.0403(7) 0.0027(6) 0.0171(6) -0.0175(6) C5A 0.0330(6) 0.0554(8) 0.0431(7) 0.0014(6) 0.0104(5) -0.0088(6) C6A 0.0327(6) 0.0358(6) 0.0320(5) 0.0010(5) 0.0058(4) 0.0025(5) C7A 0.0357(6) 0.0198(4) 0.0309(5) -0.0029(4) 0.0036(4) -0.0006(4) N1B 0.0444(6) 0.0252(5) 0.0429(6) 0.0076(4) -0.0008(4) -0.0015(4) C1B 0.0461(7) 0.0258(5) 0.0459(7) -0.0035(5) 0.0042(5) -0.0063(5) C2B 0.0460(7) 0.0293(6) 0.0368(6) -0.0024(5) 0.0091(5) -0.0073(5) C3B 0.0339(6) 0.0236(5) 0.0326(5) 0.0030(4) -0.0050(4) -0.0018(4) C4B 0.1017(13) 0.0262(6) 0.0325(6) 0.0001(5) 0.0068(7) -0.0032(7) C5B 0.0952(13) 0.0330(7) 0.0334(7) 0.0076(5) 0.0103(7) -0.0015(7) C6B 0.0321(6) 0.0251(5) 0.0410(6) 0.0065(4) -0.0074(5) -0.0030(4) C7B 0.0862(12) 0.0399(8) 0.0399(7) 0.0107(6) -0.0049(7) -0.0157(7) C8B 0.0815(12) 0.0543(10) 0.0548(9) 0.0272(8) -0.0073(9) -0.0182(8) C9B 0.0418(7) 0.0334(7) 0.0933(13) 0.0257(8) -0.0129(8) -0.0077(6) C10B 0.0432(8) 0.0270(6) 0.0943(13) 0.0024(7) 0.0046(8) -0.0072(5) C11B 0.0368(7) 0.0281(6) 0.0633(9) -0.0024(6) 0.0039(6) -0.0057(5) _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 O1A C7A 1.2948(14) . ? O1A H1OA 1.11(3) . ? O2A C7A 1.2304(14) . ? N1A C2A 1.3637(17) . ? N1A H1NA 0.882(19) . ? N1A H2NA 0.94(2) . ? C1A C6A 1.3992(16) . ? C1A C2A 1.4150(15) . ? C1A C7A 1.4917(15) . ? C2A C3A 1.4092(16) . ? C3A C4A 1.368(2) . ? C3A H3A 0.989(18) . ? C4A C5A 1.391(2) . ? C4A H4A 0.99(2) . ? C5A C6A 1.3828(18) . ? C5A H5A 0.952(19) . ? C6A H6A 0.971(15) . ? N1B C5B 1.3277(18) . ? N1B C1B 1.3308(18) . ? N1B H1OA 1.44(3) . ? C1B C2B 1.3809(17) . ? C1B H1B 0.967(19) . ? C2B C3B 1.3874(17) . ? C2B H2B 0.97(2) . ? C3B C4B 1.3919(19) . ? C3B C6B 1.4843(15) . ? C4B C5B 1.382(2) . ? C4B H4B 0.97(2) . ? C5B H5B 0.97(2) . ? C6B C11B 1.3914(18) . ? C6B C7B 1.392(2) . ? C7B C8B 1.395(2) . ? C7B H7B 0.95(2) . ? C8B C9B 1.376(3) . ? C8B H8B 0.93(3) . ? C9B C10B 1.372(3) . ? C9B H9B 0.99(2) . ? C10B C11B 1.3896(19) . ? C10B H10B 0.98(2) . ? C11B H11B 1.02(2) . ? 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 C7A O1A H1OA 115.9(13) . . ? C2A N1A H1NA 118.0(12) . . ? C2A N1A H2NA 115.3(11) . . ? H1NA N1A H2NA 121.2(16) . . ? C6A C1A C2A 119.22(10) . . ? C6A C1A C7A 118.97(10) . . ? C2A C1A C7A 121.79(10) . . ? N1A C2A C3A 119.29(11) . . ? N1A C2A C1A 122.44(11) . . ? C3A C2A C1A 118.20(11) . . ? C4A C3A C2A 121.12(12) . . ? C4A C3A H3A 121.7(10) . . ? C2A C3A H3A 117.2(10) . . ? C3A C4A C5A 121.01(12) . . ? C3A C4A H4A 119.5(12) . . ? C5A C4A H4A 119.5(12) . . ? C6A C5A C4A 118.87(13) . . ? C6A C5A H5A 120.7(11) . . ? C4A C5A H5A 120.5(11) . . ? C5A C6A C1A 121.53(12) . . ? C5A C6A H6A 119.0(8) . . ? C1A C6A H6A 119.5(8) . . ? O2A C7A O1A 123.81(10) . . ? O2A C7A C1A 122.39(10) . . ? O1A C7A C1A 113.80(10) . . ? C5B N1B C1B 117.67(11) . . ? C5B N1B H1OA 119.4(10) . . ? C1B N1B H1OA 122.7(10) . . ? N1B C1B C2B 122.75(12) . . ? N1B C1B H1B 116.3(11) . . ? C2B C1B H1B 120.9(11) . . ? C1B C2B C3B 120.39(12) . . ? C1B C2B H2B 117.4(12) . . ? C3B C2B H2B 122.2(12) . . ? C2B C3B C4B 116.12(11) . . ? C2B C3B C6B 121.90(11) . . ? C4B C3B C6B 121.97(11) . . ? C5B C4B C3B 120.01(13) . . ? C5B C4B H4B 117.0(13) . . ? C3B C4B H4B 122.9(13) . . ? N1B C5B C4B 123.03(13) . . ? N1B C5B H5B 116.5(13) . . ? C4B C5B H5B 120.5(13) . . ? C11B C6B C7B 118.10(12) . . ? C11B C6B C3B 120.83(12) . . ? C7B C6B C3B 121.07(12) . . ? C6B C7B C8B 120.69(16) . . ? C6B C7B H7B 121.0(13) . . ? C8B C7B H7B 118.3(13) . . ? C9B C8B C7B 120.05(17) . . ? C9B C8B H8B 126.1(16) . . ? C7B C8B H8B 113.7(16) . . ? C10B C9B C8B 120.02(14) . . ? C10B C9B H9B 122.1(13) . . ? C8B C9B H9B 117.8(13) . . ? C9B C10B C11B 120.22(16) . . ? C9B C10B H10B 119.9(14) . . ? C11B C10B H10B 119.9(14) . . ? C10B C11B C6B 120.91(15) . . ? C10B C11B H11B 119.8(11) . . ? C6B C11B H11B 119.2(11) . . ? _diffrn_measured_fraction_theta_max 0.969 _diffrn_reflns_theta_full 29.00 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.359 _refine_diff_density_min -0.273 _refine_diff_density_rms 0.042 #END _database_code_depnum_ccdc_archive 'CCDC 923471'