#------------------------------------------------------------------------------ #$Date: 2025-08-19 07:12:48 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301798 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/28/2012822.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_2012822 loop_ _publ_author_name 'Gawlicka-Chruszcz, Anna' 'Stadnicka, Katarzyna' _publ_section_title ; A comparative study of intermolecular interactions in the crystal structures of phenyl/phenyl end-capped oligoanilines ; _journal_issue 7 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o416 _journal_page_last o420 _journal_paper_doi 10.1107/S0108270102009472 _journal_volume 58 _journal_year 2002 _chemical_formula_moiety 'C18 H16 N2' _chemical_formula_sum 'C18 H16 N2' _chemical_formula_weight 260.33 _chemical_name_systematic N,N'-diphenyl-1,4-phenylenediamine _space_group_IT_number 61 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall '-P 2ac 2ab' _symmetry_space_group_name_H-M 'P b c a' _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL97 _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 25.678(4) _cell_length_b 7.4815(13) _cell_length_c 6.9588(12) _cell_measurement_reflns_used 38 _cell_measurement_temperature 295(2) _cell_measurement_theta_max 11.14 _cell_measurement_theta_min 1.58 _cell_volume 1336.9(4) _computing_cell_refinement 'KM-4 Software' _computing_data_collection 'KM-4 Software (Kuma Diffraction, 1995)' _computing_data_reduction 'DATAPROC (Ga\/ldecki et al., 1995)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1999)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 295(2) _diffrn_measured_fraction_theta_full 0.842 _diffrn_measured_fraction_theta_max 0.842 _diffrn_measurement_device_type 'Kuma KM-4 four-circle' _diffrn_measurement_method \q/2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.036 _diffrn_reflns_av_sigmaI/netI 0.026 _diffrn_reflns_limit_h_max 31 _diffrn_reflns_limit_h_min -31 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_limit_l_min -4 _diffrn_reflns_number 6410 _diffrn_reflns_theta_full 25.65 _diffrn_reflns_theta_max 25.65 _diffrn_reflns_theta_min 1.59 _diffrn_standards_decay_% 0.09 _diffrn_standards_interval_count 50 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.293 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 552 _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.08 _refine_diff_density_max 0.15 _refine_diff_density_min -0.16 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.144 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 123 _refine_ls_number_reflns 1269 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.144 _refine_ls_R_factor_all 0.077 _refine_ls_R_factor_gt 0.049 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0391P)^2^+0.8676P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.121 _refine_ls_wR_factor_ref 0.133 _reflns_number_gt 931 _reflns_number_total 1269 _reflns_threshold_expression I>2\s(I) _cod_data_source_file na1567.cif _cod_data_source_block II _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana The following automatic conversions were performed: '_exptl_crystal_density_meas' value 'not measured' was changed to '?' - the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas ; _cod_database_code 2012822 _cod_database_fobs_code 2012822 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' 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_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol N1 0.55620(8) 0.4452(3) 0.1576(3) 0.0509(6) Uani d . 1 . . N C1 0.60827(9) 0.4780(3) 0.1085(3) 0.0405(6) Uani d . 1 . . C C2 0.63875(10) 0.6114(4) 0.1871(3) 0.0456(6) Uani d . 1 . . C C3 0.68990(10) 0.6322(4) 0.1263(4) 0.0522(7) Uani d . 1 . . C C4 0.71117(10) 0.5234(4) -0.0113(4) 0.0567(8) Uani d . 1 . . C C5 0.67998(11) 0.3961(4) -0.0962(4) 0.0564(8) Uani d . 1 . . C C6 0.62949(11) 0.3733(4) -0.0374(4) 0.0506(7) Uani d . 1 . . C C7 0.52980(9) 0.4772(3) 0.3319(3) 0.0390(6) Uani d . 1 . . C C8 0.47676(9) 0.4446(4) 0.3342(3) 0.0424(6) Uani d . 1 . . C C9 0.55274(9) 0.5347(4) 0.5006(3) 0.0461(6) Uani d . 1 . . C H1 0.5385(10) 0.366(4) 0.083(4) 0.052(8) Uiso d . 1 . . H H2 0.6248(10) 0.699(4) 0.269(4) 0.059(8) Uiso d . 1 . . H H3 0.7108(9) 0.724(4) 0.183(4) 0.052(7) Uiso d . 1 . . H H4 0.7480(12) 0.537(4) -0.048(4) 0.062(8) Uiso d . 1 . . H H5 0.6917(11) 0.314(4) -0.198(5) 0.083(10) Uiso d . 1 . . H H6 0.6091(10) 0.292(4) -0.092(4) 0.063(9) Uiso d . 1 . . H H8 0.4617(8) 0.409(3) 0.223(3) 0.038(6) Uiso d . 1 . . H H9 0.5901(10) 0.560(4) 0.512(4) 0.063(8) 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 0.0440(12) 0.0741(16) 0.0345(11) -0.0116(11) 0.0032(9) -0.0149(11) C1 0.0396(13) 0.0514(14) 0.0303(11) 0.0049(11) 0.0003(10) 0.0049(11) C2 0.0478(15) 0.0531(16) 0.0358(13) 0.0012(12) 0.0017(11) -0.0037(12) C3 0.0480(15) 0.0648(18) 0.0438(15) -0.0076(14) -0.0033(12) 0.0012(13) C4 0.0434(14) 0.078(2) 0.0491(16) 0.0015(14) 0.0059(13) 0.0058(15) C5 0.0559(17) 0.0675(19) 0.0458(15) 0.0054(14) 0.0108(13) -0.0066(14) C6 0.0541(16) 0.0580(17) 0.0396(14) -0.0055(13) 0.0032(12) -0.0084(13) C7 0.0418(13) 0.0434(13) 0.0319(11) 0.0006(10) 0.0018(10) -0.0005(11) C8 0.0434(14) 0.0525(15) 0.0313(12) -0.0047(11) -0.0048(10) -0.0041(12) C9 0.0360(13) 0.0652(17) 0.0372(12) -0.0059(12) -0.0033(11) -0.0033(12) 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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 N1 C7 . . 129.7(2) yes C1 N1 H1 . . 117(2) no C7 N1 H1 . . 111(2) no C2 C1 C6 . . 118.2(2) yes C2 C1 N1 . . 124.8(2) yes C6 C1 N1 . . 116.9(2) yes C1 C2 C3 . . 119.7(2) yes C1 C2 H2 . . 122(2) no C3 C2 H2 . . 118(2) no C4 C3 C2 . . 121.6(3) yes C4 C3 H3 . . 120(2) no C2 C3 H3 . . 119(2) no C3 C4 C5 . . 118.6(3) yes C3 C4 H4 . . 120(2) no C5 C4 H4 . . 121(2) no C6 C5 C4 . . 120.5(3) yes C6 C5 H5 . . 115(2) no C4 C5 H5 . . 124(2) no C5 C6 C1 . . 121.2(3) yes C5 C6 H6 . . 121(2) no C1 C6 H6 . . 118(2) no C9 C7 C8 . . 117.7(2) yes C9 C7 N1 . . 125.4(2) yes C8 C7 N1 . . 117.0(2) yes C7 C8 C9 . 5_666 121.9(2) yes C7 C8 H8 . . 118.0(10) no C9 C8 H8 5_666 . 121.0(10) no C7 C9 C8 . 5_666 120.4(2) yes C7 C9 H9 . . 123(2) no C8 C9 H9 5_666 . 117(2) no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag N1 C1 . 1.402(3) yes N1 C7 . 1.410(3) yes N1 H1 . 0.91(3) no C1 C2 . 1.381(3) yes C1 C6 . 1.393(3) yes C2 C3 . 1.389(4) yes C2 H2 . 0.94(3) no C3 C4 . 1.370(4) yes C3 H3 . 0.96(3) no C4 C5 . 1.377(4) yes C4 H4 . 0.99(3) no C5 C6 . 1.370(4) yes C5 H5 . 0.98(3) no C6 H6 . 0.89(3) no C7 C8 . 1.384(3) yes C7 C9 . 1.382(3) yes C8 C9 5_666 1.386(3) yes C8 H8 . 0.90(2) no C9 C8 5_666 1.386(3) no C9 H9 . 0.98(3) no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA N1 H1 C7 3_645 0.91(3) 3.45(3) 4.140(3) 135(2) N1 H1 C8 3_645 0.91(3) 3.23(3) 3.840(4) 127(2) N1 H1 C9 3_645 0.91(3) 3.46(3) 4.297(3) 154(2) N1 H1 C9 7_565 0.91(3) 3.08(3) 3.754(4) 133(2) N1 H1 C8 7_565 0.91(3) 3.31(3) 4.211(3) 176(2) N1 H1 C7 7_565 0.91(3) 3.12(3) 3.947(3) 153(2) loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag C7 N1 C1 C2 . -28.5(4) yes C7 N1 C1 C6 . 154.9(3) no C6 C1 C2 C3 . -3.0(4) no N1 C1 C2 C3 . -179.6(2) no C1 C2 C3 C4 . 0.2(4) no C2 C3 C4 C5 . 2.9(4) no C3 C4 C5 C6 . -3.2(4) no C4 C5 C6 C1 . 0.3(4) no C2 C1 C6 C5 . 2.8(4) no N1 C1 C6 C5 . 179.6(3) no C1 N1 C7 C9 . -6.6(4) yes C1 N1 C7 C8 . 174.8(3) no C9 C7 C8 C9 5_666 -1.1(4) no N1 C7 C8 C9 5_666 177.6(2) no C8 C7 C9 C8 5_666 1.1(4) no N1 C7 C9 C8 5_666 -177.5(2) no loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 6319