#------------------------------------------------------------------------------ #$Date: 2017-10-13 01:08:28 +0100 (Fri, 13 Oct 2017) $ #$Revision: 201955 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/89/2008937.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_2008937 loop_ _publ_author_name 'S. Shanmuga Sundara Raj' 'Hoong-Kun Fun' 'Dun-ru Zhu' 'Fang-Fang Jian' 'Koulin Zhang' 'Xiao-Zeng You' _publ_section_title ; 9-(4H-1,2,4-Triazol-4-ylimino)-4,5-diazafluorene ; _journal_issue 9 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1526 _journal_page_last 1528 _journal_paper_doi 10.1107/S0108270199007908 _journal_volume 55 _journal_year 1999 _chemical_formula_sum 'C13 H8 N6' _chemical_formula_weight 248.25 _chemical_name_systematic ; 9-(4H-1,2,4-triazol-4-ylimino)-4,5-diazafluorene ; _space_group_IT_number 15 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 1 2/c 1' _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 123.7900(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 18.3040(10) _cell_length_b 10.4880(10) _cell_length_c 14.2670(10) _cell_measurement_reflns_used 2725 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 28.32 _cell_measurement_theta_min 2.36 _cell_volume 2276.2(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, PARST (Nardelli, 1995) 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 0.997 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_device_type '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 0.054 _diffrn_reflns_av_sigmaI/netI 0.0640 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 7790 _diffrn_reflns_theta_full 28.29 _diffrn_reflns_theta_max 28.29 _diffrn_reflns_theta_min 2.36 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_type none _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.449 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 1024 _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.14 _refine_diff_density_max 0.197 _refine_diff_density_min -0.228 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 172 _refine_ls_number_reflns 2817 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.018 _refine_ls_R_factor_all 0.121 _refine_ls_R_factor_gt 0.063 _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^)+(0.1040P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref 0.197 _reflns_number_gt 1553 _reflns_number_total 2817 _reflns_threshold_expression I>2\s(I) _cod_data_source_file na1425.cif _cod_data_source_block I _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_enum 1527 2010-12-29 10:47:43Z saulius 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_original_sg_symbol_H-M 'C 2/c' _cod_database_code 2008937 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -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 0.28719(12) 0.54676(19) 0.01741(18) 0.0543(6) Uani d . 1 . . N N2 0.16892(15) 0.4553(2) -0.0141(2) 0.0737(7) Uani d . 1 . . N N3 0.18406(14) 0.4119(2) -0.0933(2) 0.0696(7) Uani d . 1 . . N N4 0.35391(13) 0.6396(2) 0.05776(19) 0.0597(6) Uani d . 1 . . N N5 0.65616(12) 0.67890(19) 0.19482(18) 0.0540(6) Uani d . 1 . . N N6 0.61828(13) 0.39625(19) 0.17843(18) 0.0562(5) Uani d . 1 . . N C1 0.23120(17) 0.5360(3) 0.0496(3) 0.0686(8) Uani d . 1 . . C H1A 0.2363 0.5802 0.1095 0.082 Uiso calc R 1 . . H C2 0.25431(17) 0.4680(3) -0.0724(2) 0.0676(8) Uani d . 1 . . C H2A 0.2791 0.4559 -0.1137 0.081 Uiso calc R 1 . . H C3 0.43059(14) 0.5982(2) 0.0917(2) 0.0490(6) Uani d . 1 . . C C4 0.50250(15) 0.6913(2) 0.1266(2) 0.0519(6) Uani d . 1 . . C C5 0.50356(18) 0.8223(3) 0.1285(3) 0.0735(9) Uani d . 1 . . C H5A 0.4536 0.8697 0.1070 0.088 Uiso calc R 1 . . H C6 0.58326(19) 0.8796(3) 0.1644(3) 0.0820(9) Uani d . 1 . . C H6A 0.5877 0.9680 0.1674 0.098 Uiso calc R 1 . . H C7 0.65583(18) 0.8064(2) 0.1957(3) 0.0681(8) Uani d . 1 . . C H7A 0.7081 0.8483 0.2190 0.082 Uiso calc R 1 . . H C8 0.57854(14) 0.6259(2) 0.15952(19) 0.0477(6) Uani d . 1 . . C C9 0.55991(14) 0.4876(2) 0.15069(19) 0.0458(6) Uani d . 1 . . C C10 0.58666(18) 0.2771(3) 0.1672(3) 0.0689(8) Uani d . 1 . . C H10A 0.6252 0.2093 0.1862 0.083 Uiso calc R 1 . . H C11 0.50092(18) 0.2493(2) 0.1295(3) 0.0676(8) Uani d . 1 . . C H11A 0.4835 0.1649 0.1243 0.081 Uiso calc R 1 . . H C12 0.44105(16) 0.3457(2) 0.0995(2) 0.0558(7) Uani d . 1 . . C H12A 0.3830 0.3282 0.0738 0.067 Uiso calc R 1 . . H C13 0.47020(15) 0.4696(2) 0.10895(19) 0.0462(6) Uani d . 1 . . C 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 0.0323(10) 0.0614(12) 0.0633(13) -0.0077(10) 0.0229(10) -0.0055(11) N2 0.0484(13) 0.0881(17) 0.0845(18) -0.0217(13) 0.0368(13) -0.0125(14) N3 0.0445(12) 0.0803(16) 0.0705(15) -0.0117(12) 0.0236(11) -0.0086(13) N4 0.0363(10) 0.0625(13) 0.0769(14) -0.0093(10) 0.0293(10) -0.0085(11) N5 0.0380(10) 0.0576(12) 0.0655(13) -0.0102(9) 0.0282(10) -0.0045(10) N6 0.0423(11) 0.0529(12) 0.0670(13) -0.0028(10) 0.0264(10) 0.0050(11) C1 0.0449(14) 0.087(2) 0.0790(19) -0.0140(15) 0.0374(14) -0.0176(17) C2 0.0446(14) 0.088(2) 0.0672(17) -0.0135(14) 0.0291(13) -0.0162(16) C3 0.0363(12) 0.0570(14) 0.0532(13) -0.0057(11) 0.0245(11) -0.0026(12) C4 0.0383(12) 0.0517(14) 0.0637(15) -0.0070(11) 0.0270(12) -0.0045(12) C5 0.0483(15) 0.0542(16) 0.108(2) -0.0054(13) 0.0376(17) -0.0106(16) C6 0.0548(16) 0.0513(15) 0.127(3) -0.0122(14) 0.0421(19) -0.0128(17) C7 0.0466(15) 0.0569(16) 0.093(2) -0.0184(13) 0.0341(15) -0.0090(15) C8 0.0368(11) 0.0526(13) 0.0517(13) -0.0067(11) 0.0233(10) -0.0017(11) C9 0.0357(11) 0.0528(13) 0.0465(12) -0.0070(11) 0.0213(10) 0.0017(11) C10 0.0541(16) 0.0540(15) 0.086(2) 0.0013(13) 0.0316(15) 0.0109(14) C11 0.0550(16) 0.0486(15) 0.087(2) -0.0089(13) 0.0321(15) 0.0111(14) C12 0.0422(13) 0.0616(16) 0.0555(14) -0.0136(12) 0.0221(11) 0.0026(12) C13 0.0358(11) 0.0552(14) 0.0454(12) -0.0087(11) 0.0212(10) 0.0012(11) 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 _geom_angle_publ_flag C1 N1 C2 104.5(2) y C1 N1 N4 124.9(2) y C2 N1 N4 129.5(2) y C1 N2 N3 106.9(2) ? C2 N3 N2 106.8(2) ? C3 N4 N1 116.0(2) y C8 N5 C7 114.2(2) ? C9 N6 C10 114.5(2) ? N2 C1 N1 110.8(2) ? N3 C2 N1 111.0(2) ? N4 C3 C4 119.0(2) ? N4 C3 C13 134.6(2) y C4 C3 C13 106.35(18) ? C5 C4 C8 119.4(2) ? C5 C4 C3 131.6(2) ? C8 C4 C3 109.0(2) ? C4 C5 C6 116.2(3) ? C7 C6 C5 120.3(3) ? N5 C7 C6 124.3(2) ? N5 C8 C4 125.6(2) ? N5 C8 C9 125.9(2) ? C4 C8 C9 108.50(18) ? N6 C9 C13 125.8(2) ? N6 C9 C8 125.15(19) ? C13 C9 C8 109.00(19) ? N6 C10 C11 124.2(3) ? C12 C11 C10 120.3(2) ? C11 C12 C13 117.6(2) ? C12 C13 C9 117.5(2) ? C12 C13 C3 135.3(2) ? C9 C13 C3 107.10(19) ? 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 . 1.341(3) y N1 C2 . 1.353(3) y N1 N4 . 1.410(3) y N2 C1 . 1.299(3) y N2 N3 . 1.381(3) y N3 C2 . 1.289(3) y N4 C3 . 1.280(3) y N5 C8 . 1.336(3) y N5 C7 . 1.337(3) y N6 C9 . 1.321(3) y N6 C10 . 1.349(3) y C3 C4 . 1.485(3) ? C3 C13 . 1.485(3) ? C4 C5 . 1.374(4) ? C4 C8 . 1.378(3) ? C5 C6 . 1.386(4) ? C6 C7 . 1.376(4) ? C8 C9 . 1.479(3) ? C9 C13 . 1.414(3) ? C10 C11 . 1.378(4) ? C11 C12 . 1.372(3) ? C12 C13 . 1.383(3) ? 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 C1 H1A N5 2_655 0.93 2.57 3.381(4) 145 yes C2 H2A N5 5_665 0.93 2.50 3.361(4) 153 yes C5 H5A N2 7_565 0.93 2.62 3.513(4) 162 yes loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 4421846