#------------------------------------------------------------------------------ #$Date: 2025-08-19 07:12:48 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301798 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/10/2011065.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_2011065 loop_ _publ_author_name 'Bei, Fengli' 'Jian, Fangfang' 'Yang, Xujie' 'Lu, Lude' 'Wang, Xin' 'Shanmuga Sundara Raj, S.' 'Fun, Hoong-Kun' _publ_section_title ; 1,4-Bis(2-benzimidazolyl)benzene ; _journal_issue 6 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 718 _journal_page_last 719 _journal_paper_doi 10.1107/S0108270100003978 _journal_volume 56 _journal_year 2000 _chemical_formula_sum 'C20 H14 N4' _chemical_formula_weight 310.35 _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' _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 10.2400(3) _cell_length_b 9.7505(2) _cell_length_c 15.0310(4) _cell_measurement_reflns_used 3853 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 28.32 _cell_measurement_theta_min 2.71 _cell_volume 1500.77(7) _computing_cell_refinement 'SAINT (Siemens, 1996)' _computing_data_collection 'SMART (Siemens, 1996)' _computing_data_reduction SAINT _computing_molecular_graphics SHELXTL _computing_publication_material ; SHELXTL and PLATON (Spek, 1990) ; _computing_structure_refinement SHELXTL _computing_structure_solution 'SHELXTL (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 8.33 _diffrn_measured_fraction_theta_full .993 _diffrn_measured_fraction_theta_max .993 _diffrn_measurement_device_type ; Siemens SMART CCD area detector diffractometer ; _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .0757 _diffrn_reflns_av_sigmaI/netI .0561 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 9577 _diffrn_reflns_theta_full 28.28 _diffrn_reflns_theta_max 28.28 _diffrn_reflns_theta_min 2.71 _exptl_absorpt_coefficient_mu .085 _exptl_absorpt_correction_type none _exptl_crystal_colour 'dark red' _exptl_crystal_density_diffrn 1.374 _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 648 _exptl_crystal_size_max .50 _exptl_crystal_size_mid .12 _exptl_crystal_size_min .10 _refine_diff_density_max .185 _refine_diff_density_min -.298 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.117 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 109 _refine_ls_number_reflns 1846 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.117 _refine_ls_R_factor_all .1110 _refine_ls_R_factor_gt .0667 _refine_ls_shift/su_max .000 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0584P)^2^+0.4289P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .1551 _reflns_number_gt 1223 _reflns_number_total 1846 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file sk1369.cif _cod_data_source_block I _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 ; _cod_database_code 2011065 loop_ _symmetry_equiv_pos_as_xyz x,y,z 1/2-x,-y,1/2+z 1/2+x,1/2-y,-z -x,1/2+y,1/2-z -x,-y,-z 1/2+x,y,1/2-z 1/2-x,1/2+y,z 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 .16043(17) .05717(17) .41094(13) .0389(5) Uani d . 1 . . N N2 .20392(17) -.16702(16) .39828(12) .0377(5) Uani d . 1 . . N H2A .2467 -.2428 .4013 .045 Uiso calc R 1 . . H C1 .07906(19) -.1500(2) .36575(14) .0353(5) Uani d . 1 . . C C2 -.0120(2) -.2423(2) .33129(15) .0442(6) Uani d . 1 . . C H2B .0062 -.3355 .3272 .053 Uiso calc R 1 . . H C3 -.1289(2) -.1899(2) .30385(17) .0477(6) Uani d . 1 . . C H3A -.1913 -.2486 .2799 .057 Uiso calc R 1 . . H C4 -.1571(2) -.0490(2) .31097(17) .0491(6) Uani d . 1 . . C H4A -.2374 -.0163 .2912 .059 Uiso calc R 1 . . H C5 -.0685(2) .0409(2) .34651(17) .0458(6) Uani d . 1 . . C H5A -.0884 .1335 .3523 .055 Uiso calc R 1 . . H C6 .0526(2) -.0099(2) .37380(15) .0361(5) Uani d . 1 . . C C7 .2466(2) -.04138(19) .42458(14) .0341(5) Uani d . 1 . . C C8 .37635(19) -.02064(19) .46375(14) .0330(5) Uani d . 1 . . C C9 .4812(2) -.1039(2) .43866(16) .0391(5) Uani d . 1 . . C H9A .4680 -.1767 .3967 .047 Uiso d R 1 . . H C10 .3967(2) .0829(2) .52542(15) .0383(5) Uani d . 1 . . C H10A .3251 .1396 .5440 .046 Uiso d R 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 .0270(9) .0259(9) .0638(12) .0013(7) -.0035(8) -.0009(8) N2 .0304(9) .0240(8) .0587(11) .0004(7) -.0025(8) -.0006(8) C1 .0299(11) .0272(10) .0488(12) -.0021(8) .0002(9) .0025(9) C2 .0437(13) .0302(11) .0588(15) -.0065(10) -.0068(11) -.0008(10) C3 .0393(13) .0445(13) .0594(15) -.0134(10) -.0090(11) .0019(12) C4 .0321(12) .0512(14) .0640(15) -.0023(10) -.0091(11) .0079(12) C5 .0354(13) .0332(11) .0688(16) .0013(9) -.0041(11) .0026(11) C6 .0277(10) .0288(10) .0516(13) -.0017(8) .0009(9) .0014(9) C7 .0286(11) .0241(9) .0496(12) -.0009(8) .0005(9) .0002(9) C8 .0261(10) .0254(9) .0475(12) .0002(8) .0006(9) .0009(9) C9 .0340(12) .0290(10) .0545(13) .0046(9) -.0018(10) -.0088(10) C10 .0291(11) .0329(11) .0529(13) .0051(9) .0034(10) -.0043(9) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0061 .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 _geom_angle_publ_flag C7 N1 C6 . 104.4(2) y C7 N2 C1 . 107.0(2) y C7 N2 H2A . 126.5 ? C1 N2 H2A . 126.5 ? N2 C1 C2 . 132.37(19) ? N2 C1 C6 . 105.46(17) ? C2 C1 C6 . 122.16(19) ? C3 C2 C1 . 117.2(2) ? C3 C2 H2B . 121.4 ? C1 C2 H2B . 121.4 ? C2 C3 C4 . 121.5(2) ? C2 C3 H3A . 119.3 ? C4 C3 H3A . 119.3 ? C5 C4 C3 . 121.2(2) ? C5 C4 H4A . 119.4 ? C3 C4 H4A . 119.4 ? C4 C5 C6 . 118.4(2) ? C4 C5 H5A . 120.8 ? C6 C5 H5A . 120.8 ? C5 C6 C1 . 119.57(19) ? C5 C6 N1 . 130.68(19) ? C1 C6 N1 . 109.75(17) ? N1 C7 N2 . 113.34(18) ? N1 C7 C8 . 124.54(17) ? N2 C7 C8 . 122.13(17) ? C10 C8 C9 . 119.20(19) ? C10 C8 C7 . 120.32(18) ? C9 C8 C7 . 120.48(19) ? C10 C9 C8 5_656 120.4(2) ? C10 C9 H9A 5_656 119.7 ? C8 C9 H9A . 120.0 ? C9 C10 C8 5_656 120.45(19) ? C9 C10 H10A 5_656 119.6 ? C8 C10 H10A . 119.9 ? 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 C7 . 1.320(3) y N1 C6 . 1.400(3) y N2 C7 . 1.359(2) y N2 C1 . 1.379(3) y N2 H2A . .8600 ? C1 C2 . 1.395(3) ? C1 C6 . 1.398(3) ? C2 C3 . 1.365(3) ? C2 H2B . .9300 ? C3 C4 . 1.409(3) ? C3 H3A . .9300 ? C4 C5 . 1.370(3) ? C4 H4A . .9300 ? C5 C6 . 1.396(3) ? C5 H5A . .9300 ? C7 C8 . 1.468(3) ? C8 C10 . 1.386(3) y C8 C9 . 1.398(3) y C9 C10 5_656 1.377(3) y C9 H9A . .9600 ? C10 C9 5_656 1.377(3) y C10 H10A . .9600 ? 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 _geom_hbond_publ_flag N2 H2A N1 7_545 .86 2.17 3.033(2) 175.27 yes 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 C7 N2 C1 C2 . -179.0(2) C7 N2 C1 C6 . .5(2) N2 C1 C2 C3 . -179.5(2) C6 C1 C2 C3 . 1.1(3) C1 C2 C3 C4 . -.7(4) C2 C3 C4 C5 . -.6(4) C3 C4 C5 C6 . 1.5(4) C4 C5 C6 C1 . -1.1(3) C4 C5 C6 N1 . 179.3(2) N2 C1 C6 C5 . -179.7(2) C2 C1 C6 C5 . -.2(3) N2 C1 C6 N1 . -.1(2) C2 C1 C6 N1 . 179.5(2) C7 N1 C6 C5 . 179.2(2) C7 N1 C6 C1 . -.4(2) C6 N1 C7 N2 . .7(2) C6 N1 C7 C8 . -179.5(2) C1 N2 C7 N1 . -.8(3) C1 N2 C7 C8 . 179.42(19) N1 C7 C8 C10 . 30.6(3) N2 C7 C8 C10 . -149.6(2) N1 C7 C8 C9 . -148.6(2) N2 C7 C8 C9 . 31.1(3) C10 C8 C9 C10 5_656 -.2(4) C7 C8 C9 C10 5_656 179.1(2) C9 C8 C10 C9 5_656 .2(4) C7 C8 C10 C9 5_656 -179.1(2) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 830749