#------------------------------------------------------------------------------ #$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301791 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/84/2008400.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_2008400 loop_ _publ_author_name 'Hoong-Kun Fun' 'Kandasamy Chinnakali' 'Xiao-Feng Chen' 'Xu-Hui Zhu' 'Xiao-Zeng You' _publ_section_title ; (1H-Imidazol-2-yl)phenyldiazene ; _journal_issue 4 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first IUC9900025 _journal_paper_doi 10.1107/S0108270199099631 _journal_volume 55 _journal_year 1999 _chemical_formula_sum 'C9 H8 N4' _chemical_formula_weight 172.19 _chemical_name_systematic ; 2-(Arylazo)imidazole ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 109.4510(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 7.33100(10) _cell_length_b 14.0055(3) _cell_length_c 9.2714(2) _cell_measurement_reflns_used 3015 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 28.28 _cell_measurement_theta_min 2.75 _cell_volume 897.60(3) _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_measurement_device 'Siemens SMART CCD area-detector' _diffrn_measurement_method \w _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 0.030 _diffrn_reflns_av_sigmaI/netI 0.036 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 6062 _diffrn_reflns_theta_max 28.28 _diffrn_reflns_theta_min 2.75 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type none _exptl_crystal_colour red _exptl_crystal_density_diffrn 1.274 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 360 _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.46 _exptl_crystal_size_min 0.38 _refine_diff_density_max 0.12 _refine_diff_density_min -0.11 _refine_ls_extinction_coef 0.024(6) _refine_ls_extinction_method SHELXTL _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 151 _refine_ls_number_reflns 2213 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.023 _refine_ls_R_factor_all 0.074 _refine_ls_R_factor_gt 0.043 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0676P)^2^+0.0196P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref 0.131 _reflns_number_gt 1412 _reflns_number_total 2213 _reflns_threshold_expression I>2\s(I) _cod_data_source_file qa0098.cif _cod_data_source_block I _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 2008400 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' 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 0.13832(18) 0.20474(8) 0.11385(13) 0.0719(4) Uani d . 1 . . N N2 -0.07892(16) 0.22661(8) -0.11550(12) 0.0596(3) Uani d . 1 . . N N3 0.15521(15) 0.35350(8) -0.00204(12) 0.0579(3) Uani d . 1 . . N N4 0.09088(15) 0.39558(8) -0.12885(12) 0.0600(3) Uani d . 1 . . N C1 0.07253(18) 0.26436(9) -0.00288(13) 0.0551(3) Uani d . 1 . . C C2 0.0227(3) 0.12647(12) 0.07218(19) 0.0845(5) Uani d . 1 . . C C3 -0.1110(2) 0.13957(11) -0.06791(17) 0.0754(5) Uani d . 1 . . C C4 0.16673(19) 0.48857(10) -0.13118(16) 0.0608(4) Uani d . 1 . . C C5 0.1190(3) 0.53123(15) -0.2734(2) 0.0861(5) Uani d . 1 . . C C6 0.1848(4) 0.62171(17) -0.2874(3) 0.1080(7) Uani d . 1 . . C C7 0.2965(3) 0.67022(15) -0.1607(3) 0.0984(6) Uani d . 1 . . C C8 0.3443(3) 0.62893(13) -0.0189(2) 0.0835(5) Uani d . 1 . . C C9 0.2808(2) 0.53841(12) -0.00297(19) 0.0698(4) Uani d . 1 . . C H1 -0.155(2) 0.2556(11) -0.2009(19) 0.076(4) Uiso d . 1 . . H H8 0.430(3) 0.6678(13) 0.077(2) 0.101(6) Uiso d . 1 . . H H5 0.039(3) 0.4937(12) -0.357(2) 0.097(6) Uiso d . 1 . . H H3 -0.211(3) 0.0983(13) -0.128(2) 0.092(5) Uiso d . 1 . . H H2 0.033(2) 0.0718(12) 0.136(2) 0.093(5) Uiso d . 1 . . H H9 0.315(2) 0.5067(12) 0.098(2) 0.086(5) Uiso d . 1 . . H H6 0.149(3) 0.6494(17) -0.387(3) 0.147(9) Uiso d . 1 . . H H7 0.341(3) 0.7351(16) -0.170(2) 0.118(7) 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 0.0777(8) 0.0655(8) 0.0503(6) 0.0041(6) -0.0082(6) 0.0017(5) N2 0.0581(6) 0.0623(7) 0.0437(6) 0.0029(5) -0.0024(5) -0.0030(5) N3 0.0512(6) 0.0652(7) 0.0485(6) 0.0059(5) 0.0046(4) -0.0043(5) N4 0.0560(6) 0.0694(7) 0.0491(6) 0.0051(5) 0.0102(5) -0.0014(5) C1 0.0514(7) 0.0602(8) 0.0421(6) 0.0070(6) 0.0003(5) -0.0042(5) C2 0.1039(12) 0.0647(10) 0.0626(9) -0.0025(9) -0.0020(8) 0.0076(7) C3 0.0810(10) 0.0634(9) 0.0631(9) -0.0095(8) -0.0010(8) -0.0041(7) C4 0.0553(7) 0.0653(9) 0.0639(8) 0.0061(6) 0.0226(6) -0.0010(6) C5 0.0979(12) 0.0889(12) 0.0697(11) -0.0052(10) 0.0253(9) 0.0087(9) C6 0.1334(18) 0.1002(16) 0.0980(15) -0.0052(13) 0.0485(14) 0.0234(12) C7 0.1102(14) 0.0751(13) 0.1299(18) -0.0078(11) 0.0666(14) 0.0006(12) C8 0.0797(11) 0.0748(11) 0.1050(14) -0.0072(8) 0.0428(10) -0.0157(9) C9 0.0676(8) 0.0697(10) 0.0727(10) 0.0001(7) 0.0243(7) -0.0077(7) 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 C1 N1 C2 104.66(12) C3 N2 C1 106.83(11) C3 N2 H1 125.1(10) C1 N2 H1 127.6(10) N4 N3 C1 112.92(10) N3 N4 C4 114.67(11) N1 C1 N2 111.49(13) N1 C1 N3 121.58(11) N2 C1 N3 126.94(11) C3 C2 N1 110.29(15) C3 C2 H2 125.9(11) N1 C2 H2 123.8(11) N2 C3 C2 106.74(13) N2 C3 H3 123.0(11) C2 C3 H3 130.2(11) C5 C4 C9 119.15(16) C5 C4 N4 115.81(14) C9 C4 N4 125.04(13) C6 C5 C4 120.18(19) C6 C5 H5 124.5(11) C4 C5 H5 115.3(11) C7 C6 C5 120.3(2) C7 C6 H6 121.4(15) C5 C6 H6 118.4(15) C6 C7 C8 120.20(19) C6 C7 H7 120.4(12) C8 C7 H7 119.4(12) C7 C8 C9 120.28(18) C7 C8 H8 118.9(10) C9 C8 H8 120.8(10) C8 C9 C4 119.94(17) C8 C9 H9 121.8(10) C4 C9 H9 118.2(10) 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 . 1.324(2) yes N1 C2 . 1.361(2) yes N2 C3 . 1.344(2) yes N2 C1 . 1.353(2) yes N2 H1 . 0.90(2) ? N3 N4 . 1.258(2) yes N3 C1 . 1.387(2) yes N4 C4 . 1.419(2) yes C2 C3 . 1.354(2) yes C2 H2 . 0.957(18) ? C3 H3 . 0.954(18) ? C4 C5 . 1.382(2) ? C4 C9 . 1.392(2) ? C5 C6 . 1.377(3) ? C5 H5 . 0.959(19) ? C6 C7 . 1.368(3) ? C6 H6 . 0.95(3) ? C7 C8 . 1.371(3) ? C7 H7 . 0.98(2) ? C8 C9 . 1.376(2) ? C8 H8 . 1.053(19) ? C9 H9 . 0.986(19) ? 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 H1 N1 4_565 0.90(2) 1.96(2) 2.838(2) 167.0(10) 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 _geom_torsion_publ_flag C1 N3 N4 C4 177.80(10) yes C2 N1 C1 N2 -0.06(18) ? C2 N1 C1 N3 179.79(14) ? C3 N2 C1 N1 0.27(17) ? C3 N2 C1 N3 -179.58(13) ? N4 N3 C1 N1 171.68(12) ? N4 N3 C1 N2 -8.5(2) yes C1 N1 C2 C3 -0.2(2) ? C1 N2 C3 C2 -0.36(19) ? N1 C2 C3 N2 0.3(2) ? N3 N4 C4 C5 171.57(13) ? N3 N4 C4 C9 -9.2(2) yes C9 C4 C5 C6 0.4(3) ? N4 C4 C5 C6 179.63(17) ? C4 C5 C6 C7 -0.5(3) ? C5 C6 C7 C8 0.3(4) ? C6 C7 C8 C9 0.1(3) ? C7 C8 C9 C4 -0.3(3) ? C5 C4 C9 C8 0.0(2) ? N4 C4 C9 C8 -179.19(13) ? loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 13565465 2 PubChem 72551