#------------------------------------------------------------------------------ #$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/2014705.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2014705 loop_ _publ_author_name 'Wang, Qing' 'Pi, Xiang-Dong' 'Su, Cheng-Yong' _publ_section_title ; Bis[4-(3-pyridylmethyleneamino)phenyl]methane ; _journal_issue 2 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o73 _journal_page_last o74 _journal_volume 61 _journal_year 2005 _chemical_formula_iupac 'C25 H20 N4' _chemical_formula_moiety 'C25 H20 N4' _chemical_formula_sum 'C25 H20 N4' _chemical_formula_weight 376.45 _chemical_name_systematic ; Bis[4-(3-pyridylmethyleneamino)phenyl]methane ; _space_group_IT_number 7 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall 'P -2yc' _symmetry_space_group_name_H-M 'P 1 c 1' _audit_creation_method 'WinGX routine CIF_UPDATE' _cell_angle_alpha 90 _cell_angle_beta 98.394(10) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 18.7505(10) _cell_length_b 4.6414(10) _cell_length_c 11.3866(10) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 17.64 _cell_measurement_theta_min 8 _cell_volume 980.3(2) _computing_cell_refinement 'CAD-4 EXPRESS' _computing_data_collection 'CAD-4 EXPRESS (Enraf-Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_molecular_graphics SHELXL97 _computing_publication_material 'Please provide missing information' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_device_type 'Enraf Nonius CAD-4' _diffrn_measurement_method \w _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0351 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 3793 _diffrn_reflns_theta_full 26 _diffrn_reflns_theta_max 26 _diffrn_reflns_theta_min 2.2 _diffrn_standards_decay_% <97% _diffrn_standards_interval_count 3600 _diffrn_standards_interval_time 400 _diffrn_standards_number 2 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_T_max 0.980 _exptl_absorpt_correction_T_min 0.956 _exptl_absorpt_correction_type '\y scan' _exptl_absorpt_process_details '(North et al., 1968)' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.275 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 396 _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.26 _refine_diff_density_max 0.108 _refine_diff_density_min -0.099 _refine_ls_extinction_coef 0.028(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL97 (Sheldrick, 1997)' _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 343 _refine_ls_number_reflns 1920 _refine_ls_number_restraints 2 _refine_ls_restrained_S_all 1.02 _refine_ls_R_factor_gt 0.0351 _refine_ls_shift/su_max 0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.031P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref 0.0706 _reflns_number_gt 1287 _reflns_number_total 1920 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file hj1037.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M Pc _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_code 2014705 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_occupancy _atom_site_type_symbol N1 1.38687(18) 0.3314(9) 1.4166(3) 0.0875(12) Uani d 1 N N2 1.21014(14) -0.0157(6) 1.1031(2) 0.0585(8) Uani d 1 N N3 0.74195(14) 0.1956(5) 0.6940(2) 0.0434(7) Uani d 1 N N4 0.60546(19) 0.7947(7) 0.4941(3) 0.0774(10) Uani d 1 N C1 1.3264(2) 0.1870(10) 1.3719(3) 0.0736(12) Uani d 1 C C2 1.4176(2) 0.4898(11) 1.3394(5) 0.0833(13) Uani d 1 C C3 1.3924(2) 0.5013(10) 1.2211(4) 0.0753(12) Uani d 1 C C4 1.3322(2) 0.3496(9) 1.1778(4) 0.0656(10) Uani d 1 C C5 1.29817(17) 0.1853(8) 1.2537(3) 0.0558(9) Uani d 1 C C6 1.23284(18) 0.0183(8) 1.2119(3) 0.0589(9) Uani d 1 C C7 1.14446(17) -0.1646(7) 1.0697(3) 0.0515(9) Uani d 1 C C8 1.1390(2) -0.3547(9) 0.9741(3) 0.0620(10) Uani d 1 C C9 1.07583(19) -0.4965(9) 0.9364(3) 0.0590(9) Uani d 1 C C10 1.01474(16) -0.4492(6) 0.9883(3) 0.0449(8) Uani d 1 C C11 1.01964(19) -0.2567(7) 1.0809(3) 0.0493(8) Uani d 1 C C12 1.08326(19) -0.1167(8) 1.1219(3) 0.0506(8) Uani d 1 C C13 0.94456(19) -0.5996(8) 0.9437(3) 0.0502(9) Uani d 1 C C14 0.88863(15) -0.3967(6) 0.8794(3) 0.0409(8) Uani d 1 C C15 0.89570(18) -0.2901(7) 0.7680(3) 0.0473(8) Uani d 1 C C16 0.84642(17) -0.1021(7) 0.7103(3) 0.0448(8) Uani d 1 C C17 0.78862(16) -0.0037(6) 0.7618(3) 0.0383(7) Uani d 1 C C18 0.78076(18) -0.1103(7) 0.8731(3) 0.0445(8) Uani d 1 C C19 0.82977(16) -0.3062(7) 0.9295(3) 0.0417(8) Uani d 1 C C20 0.69408(18) 0.3254(7) 0.7398(3) 0.0459(8) Uani d 1 C C21 0.64497(16) 0.5350(7) 0.6741(3) 0.0440(8) Uani d 1 C C22 0.59340(19) 0.6733(8) 0.7285(4) 0.0635(10) Uani d 1 C C23 0.5481(2) 0.8671(9) 0.6633(4) 0.0695(12) Uani d 1 C C24 0.5556(2) 0.9178(9) 0.5486(4) 0.0665(12) Uani d 1 C C25 0.6488(2) 0.6058(8) 0.5587(3) 0.0608(10) Uani d 1 C H16 0.8509(15) -0.025(7) 0.634(3) 0.046(8) Uiso d 1 H H15 0.9368(17) -0.346(7) 0.738(3) 0.054(9) Uiso d 1 H H18 0.7402(13) -0.058(6) 0.910(2) 0.030(7) Uiso d 1 H H24 0.5257(15) 1.058(7) 0.507(3) 0.046(9) Uiso d 1 H H13B 0.9250(16) -0.695(7) 1.012(3) 0.059(9) Uiso d 1 H H25 0.686(2) 0.504(8) 0.509(3) 0.089(12) Uiso d 1 H H13A 0.9534(15) -0.754(7) 0.891(3) 0.047(9) Uiso d 1 H H11 0.9790(15) -0.233(6) 1.116(2) 0.033(8) Uiso d 1 H H9 1.0757(19) -0.618(8) 0.872(3) 0.079(12) Uiso d 1 H H2 1.464(2) 0.605(10) 1.368(4) 0.109(15) Uiso d 1 H H8 1.182(2) -0.369(8) 0.939(3) 0.079(12) Uiso d 1 H H23 0.514(2) 0.973(9) 0.703(4) 0.091(13) Uiso d 1 H H20 0.6855(19) 0.281(8) 0.825(4) 0.083(11) Uiso d 1 H H1 1.3054(18) 0.053(8) 1.429(3) 0.070(11) Uiso d 1 H H4 1.314(2) 0.339(8) 1.102(3) 0.079(13) Uiso d 1 H H12 1.0836(15) 0.016(6) 1.184(3) 0.042(8) Uiso d 1 H H19 0.8250(16) -0.393(6) 1.007(3) 0.059(9) Uiso d 1 H H6 1.207(2) -0.095(8) 1.273(3) 0.085(12) Uiso d 1 H H22 0.5898(18) 0.630(7) 0.813(3) 0.074(11) Uiso d 1 H H3 1.414(2) 0.625(8) 1.174(4) 0.082(14) Uiso d 1 H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 N1 0.065(2) 0.123(3) 0.070(2) -0.004(2) -0.0091(19) -0.024(2) N2 0.0473(16) 0.0663(18) 0.0593(19) -0.0064(15) -0.0009(14) -0.0007(15) N3 0.0451(15) 0.0446(16) 0.0409(15) 0.0044(13) 0.0073(13) 0.0003(13) N4 0.091(3) 0.085(2) 0.053(2) 0.035(2) -0.0018(19) 0.0046(18) C1 0.061(3) 0.100(3) 0.060(2) 0.005(2) 0.007(2) -0.004(2) C2 0.056(2) 0.092(3) 0.099(4) -0.012(3) 0.001(3) -0.026(3) C3 0.057(2) 0.081(3) 0.087(3) -0.009(2) 0.008(2) -0.007(3) C4 0.057(2) 0.077(3) 0.059(2) -0.005(2) -0.0021(19) -0.006(2) C5 0.044(2) 0.067(2) 0.055(2) 0.0040(17) 0.0014(16) -0.0020(19) C6 0.054(2) 0.060(2) 0.060(3) -0.0026(19) 0.0038(19) 0.0053(19) C7 0.0447(19) 0.055(2) 0.052(2) 0.0002(18) -0.0016(16) 0.0051(18) C8 0.048(2) 0.080(3) 0.058(2) -0.003(2) 0.0109(18) -0.007(2) C9 0.060(2) 0.067(2) 0.049(2) 0.002(2) 0.0032(18) -0.0112(19) C10 0.053(2) 0.0359(17) 0.0440(17) 0.0036(15) -0.0003(15) 0.0070(15) C11 0.048(2) 0.049(2) 0.052(2) 0.0024(16) 0.0088(16) 0.0018(17) C12 0.054(2) 0.048(2) 0.048(2) -0.0002(17) 0.0000(17) -0.0053(17) C13 0.058(2) 0.0415(19) 0.048(2) -0.0005(17) -0.0035(17) 0.0029(17) C14 0.0438(18) 0.0362(17) 0.0404(17) -0.0084(15) -0.0016(14) 0.0019(15) C15 0.047(2) 0.048(2) 0.048(2) 0.0042(16) 0.0116(16) 0.0014(16) C16 0.055(2) 0.0472(19) 0.0329(17) 0.0066(16) 0.0084(15) 0.0035(15) C17 0.0441(17) 0.0348(15) 0.0353(16) -0.0039(14) 0.0033(14) -0.0006(14) C18 0.0471(19) 0.0464(19) 0.0415(19) -0.0003(16) 0.0112(16) 0.0003(16) C19 0.050(2) 0.0416(18) 0.0322(17) -0.0057(15) 0.0026(14) 0.0033(15) C20 0.054(2) 0.0423(18) 0.0417(19) 0.0000(17) 0.0075(17) 0.0003(16) C21 0.0411(17) 0.0433(18) 0.047(2) 0.0014(15) 0.0046(15) -0.0039(16) C22 0.062(2) 0.066(2) 0.066(3) 0.011(2) 0.021(2) 0.010(2) C23 0.054(2) 0.062(2) 0.094(3) 0.017(2) 0.019(2) 0.009(2) C24 0.064(3) 0.055(2) 0.072(3) 0.009(2) -0.018(2) 0.002(2) C25 0.076(3) 0.062(2) 0.043(2) 0.018(2) 0.0051(19) -0.0015(19) 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 0 '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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C2 N1 C1 116.2(4) C6 N2 C7 118.8(3) C20 N3 C17 120.5(2) C24 N4 C25 116.0(4) N1 C1 C5 123.7(4) N1 C1 H1 116.5(19) C5 C1 H1 119(2) N1 C2 C3 123.4(4) N1 C2 H2 120(2) C3 C2 H2 117(3) C4 C3 C2 119.2(5) C4 C3 H3 121(3) C2 C3 H3 119(3) C3 C4 C5 119.7(4) C3 C4 H4 125(3) C5 C4 H4 116(3) C1 C5 C4 117.7(4) C1 C5 C6 120.3(4) C4 C5 C6 122.0(3) N2 C6 C5 122.1(3) N2 C6 H6 118(2) C5 C6 H6 120(2) C12 C7 C8 117.8(3) C12 C7 N2 123.3(3) C8 C7 N2 118.8(3) C9 C8 C7 120.8(4) C9 C8 H8 126(2) C7 C8 H8 113(2) C8 C9 C10 121.5(4) C8 C9 H9 116(2) C10 C9 H9 122(2) C11 C10 C9 117.7(3) C11 C10 C13 121.0(3) C9 C10 C13 121.2(3) C10 C11 C12 121.6(3) C10 C11 H11 116.5(17) C12 C11 H11 121.9(17) C11 C12 C7 120.6(3) C11 C12 H12 118.4(18) C7 C12 H12 121.0(18) C10 C13 C14 112.5(3) C10 C13 H13B 109.7(18) C14 C13 H13B 109.9(18) C10 C13 H13A 109.4(17) C14 C13 H13A 109.1(18) H13B C13 H13A 106(3) C19 C14 C15 117.3(3) C19 C14 C13 121.9(3) C15 C14 C13 120.8(3) C16 C15 C14 121.3(3) C16 C15 H15 122.6(19) C14 C15 H15 116.0(19) C15 C16 C17 121.6(3) C15 C16 H16 122.2(18) C17 C16 H16 116.1(18) C16 C17 C18 117.6(3) C16 C17 N3 116.3(3) C18 C17 N3 126.1(3) C19 C18 C17 120.5(3) C19 C18 H18 118.6(16) C17 C18 H18 120.8(16) C14 C19 C18 121.7(3) C14 C19 H19 115.3(18) C18 C19 H19 123.0(18) N3 C20 C21 122.7(3) N3 C20 H20 121(2) C21 C20 H20 116(2) C25 C21 C22 117.3(3) C25 C21 C20 122.2(3) C22 C21 C20 120.5(3) C23 C22 C21 118.6(4) C23 C22 H22 122(2) C21 C22 H22 119(2) C24 C23 C22 119.3(4) C24 C23 H23 122(2) C22 C23 H23 118(2) N4 C24 C23 123.8(4) N4 C24 H24 118.1(19) C23 C24 H24 118.0(18) N4 C25 C21 124.9(4) N4 C25 H25 113(2) C21 C25 H25 122(2) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance N1 C2 1.339(6) N1 C1 1.351(5) N2 C6 1.259(4) N2 C7 1.415(4) N3 C20 1.256(3) N3 C17 1.421(4) N4 C24 1.325(5) N4 C25 1.340(5) C1 C5 1.373(5) C1 H1 1.02(4) C2 C3 1.362(6) C2 H2 1.03(5) C3 C4 1.361(5) C3 H3 0.92(4) C4 C5 1.377(5) C4 H4 0.88(4) C5 C6 1.469(4) C6 H6 1.05(4) C7 C12 1.385(5) C7 C8 1.393(5) C8 C9 1.369(5) C8 H8 0.96(4) C9 C10 1.381(4) C9 H9 0.93(4) C10 C11 1.375(5) C10 C13 1.511(5) C11 C12 1.379(5) C11 H11 0.92(3) C12 H12 0.93(3) C13 C14 1.516(4) C13 H13B 1.01(4) C13 H13A 0.97(3) C14 C19 1.380(4) C14 C15 1.386(4) C15 C16 1.367(5) C15 H15 0.93(3) C16 C17 1.383(4) C16 H16 0.96(3) C17 C18 1.388(4) C18 C19 1.382(4) C18 H18 0.95(3) C19 H19 0.98(3) C20 C21 1.467(4) C20 H20 1.03(4) C21 C25 1.367(5) C21 C22 1.381(5) C22 C23 1.377(5) C22 H22 1.00(4) C23 C24 1.355(6) C23 H23 0.98(4) C24 H24 0.94(3) C25 H25 1.07(4) loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion C2 N1 C1 C5 3.1(6) C1 N1 C2 C3 -2.4(7) N1 C2 C3 C4 1.3(7) C2 C3 C4 C5 -0.6(6) N1 C1 C5 C4 -2.6(6) N1 C1 C5 C6 178.9(3) C3 C4 C5 C1 1.2(6) C3 C4 C5 C6 179.7(4) C7 N2 C6 C5 -176.2(3) C1 C5 C6 N2 -171.6(4) C4 C5 C6 N2 10.0(5) C6 N2 C7 C12 44.3(5) C6 N2 C7 C8 -140.4(3) C12 C7 C8 C9 -2.3(5) N2 C7 C8 C9 -178.0(4) C7 C8 C9 C10 2.4(6) C8 C9 C10 C11 -0.9(5) C8 C9 C10 C13 178.1(3) C9 C10 C11 C12 -0.6(5) C13 C10 C11 C12 -179.6(3) C10 C11 C12 C7 0.6(5) C8 C7 C12 C11 0.8(5) N2 C7 C12 C11 176.3(3) C11 C10 C13 C14 70.4(4) C9 C10 C13 C14 -108.6(4) C10 C13 C14 C19 -106.9(3) C10 C13 C14 C15 71.8(4) C19 C14 C15 C16 0.2(4) C13 C14 C15 C16 -178.5(3) C14 C15 C16 C17 1.9(5) C15 C16 C17 C18 -2.2(5) C15 C16 C17 N3 178.8(3) C20 N3 C17 C16 -170.3(3) C20 N3 C17 C18 10.7(4) C16 C17 C18 C19 0.5(4) N3 C17 C18 C19 179.4(3) C15 C14 C19 C18 -1.9(4) C13 C14 C19 C18 176.8(3) C17 C18 C19 C14 1.6(5) C17 N3 C20 C21 179.4(3) N3 C20 C21 C25 -0.9(5) N3 C20 C21 C22 -179.7(3) C25 C21 C22 C23 1.6(5) C20 C21 C22 C23 -179.6(3) C21 C22 C23 C24 -0.4(6) C25 N4 C24 C23 1.5(6) C22 C23 C24 N4 -1.2(6) C24 N4 C25 C21 -0.2(6) C22 C21 C25 N4 -1.3(6) C20 C21 C25 N4 179.9(4)