#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/05/2200591.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_2200591 loop_ _publ_author_name 'O'Brien, John G.' 'Grousnick, Katherine E.' 'Baughman, Russell G.' _publ_section_title ; 2-Cyano-2'-nitrodiazoaminobenzene ; _journal_issue 10 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o919 _journal_page_last o921 _journal_paper_doi 10.1107/S160053680101443X _journal_volume 57 _journal_year 2001 _chemical_formula_moiety 'C13 H9 N5 O2' _chemical_formula_sum 'C13 H9 N5 O2' _chemical_formula_weight 267.25 _chemical_name_common 2-cyano-2'-nitrodiazoaminobenzene _chemical_name_systematic ; 2-cyano-2'-nitrodiazoaminobenzene ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _audit_creation_method SHELXL _cell_angle_alpha 79.099(7) _cell_angle_beta 74.695(4) _cell_angle_gamma 69.379(6) _cell_formula_units_Z 2 _cell_length_a 7.2080(10) _cell_length_b 8.0106(12) _cell_length_c 12.256(2) _cell_measurement_reflns_used 100 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 12.5 _cell_measurement_theta_min 5.2 _cell_volume 635.20(17) _computing_cell_refinement ; P3/P4-PC Diffractometer Program (Siemens, 1991a) ; _computing_data_collection ; P3/P4-PC Diffractometer Program (Siemens, 1991a) ; _computing_data_reduction 'XDISK (Siemens, 1991b)' _computing_molecular_graphics 'SHELXTL/PC (Sheldrick, 1990b)' _computing_publication_material ; SHELXTL/PC (Sheldrick, 1990b) & SHELXL93 (Sheldrick, 1993) ; _computing_structure_refinement 'SHELXL93 (Sheldrick, 1993)' _computing_structure_solution 'SHELXS90 (Sheldrick, 1990a)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full .99 _diffrn_measured_fraction_theta_max .99 _diffrn_measurement_device 'Siemens Bruker P4 diffractometer' _diffrn_measurement_method \q/2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .0296 _diffrn_reflns_av_sigmaI/netI .0461 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 2825 _diffrn_reflns_theta_full 25.0 _diffrn_reflns_theta_max 24.99 _diffrn_reflns_theta_min 2.73 _diffrn_standards_decay_% 2.0 _diffrn_standards_interval_count 100 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu .100 _exptl_absorpt_correction_type none _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.397 _exptl_crystal_density_meas ? _exptl_crystal_description 'triangular plate' _exptl_crystal_F_000 276 _exptl_crystal_size_max .55 _exptl_crystal_size_mid .40 _exptl_crystal_size_min .18 _refine_diff_density_max .488 _refine_diff_density_min -.164 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_all 1.055 _refine_ls_goodness_of_fit_ref 1.182 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 181 _refine_ls_number_reflns 2233 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.081 _refine_ls_restrained_S_obs 1.182 _refine_ls_R_factor_all .1100 _refine_ls_R_factor_gt .0581 _refine_ls_shift/su_max .000 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0913P)^2^+0.1553P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all .1963 _refine_ls_wR_factor_ref .1594 _reflns_number_gt 1303 _reflns_number_total 2247 _reflns_threshold_expression I>2\s(I) _cod_data_source_file bt6074.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic' 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 'Triclinic' changed to 'triclinic' 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_original_cell_volume 635.2(2) _cod_original_sg_symbol_H-M P-1 _cod_database_code 2200591 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' 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 O1 .126(3) .0521(15) .094(2) -.045(2) -.021(2) -.0006(14) O2 .140(3) .063(2) .064(2) -.034(2) -.011(2) -.0227(13) N1 .069(2) .0438(15) .058(2) -.0200(14) -.0146(15) -.0053(13) N2 .066(2) .0446(15) .0410(14) -.0227(13) -.0088(13) -.0062(11) N3 .051(2) .048(2) .0421(14) -.0187(12) -.0088(12) -.0043(11) N4 .064(2) .051(2) .0409(15) -.0205(14) -.0110(13) -.0041(12) N5 .124(3) .079(2) .080(2) -.024(2) -.018(2) -.023(2) C1 .040(2) .044(2) .038(2) -.0166(13) -.0036(13) -.0067(13) C2 .045(2) .039(2) .049(2) -.0168(13) -.0102(14) -.0053(13) C3 .056(2) .053(2) .044(2) -.020(2) -.0083(15) .0011(14) C4 .068(2) .068(2) .036(2) -.026(2) -.008(2) -.008(2) C5 .065(2) .055(2) .050(2) -.021(2) -.009(2) -.015(2) C6 .060(2) .044(2) .047(2) -.021(2) -.007(2) -.0063(14) C7 .046(2) .048(2) .045(2) -.0166(14) -.0103(14) -.0035(14) C8 .047(2) .050(2) .046(2) -.0158(15) -.0130(14) -.0010(14) C9 .056(2) .062(2) .048(2) -.020(2) -.013(2) .004(2) C10 .066(2) .052(2) .070(2) -.026(2) -.023(2) .013(2) C11 .076(3) .048(2) .074(2) -.025(2) -.028(2) -.005(2) C12 .065(2) .057(2) .049(2) -.024(2) -.015(2) -.007(2) C13 .068(2) .053(2) .039(2) -.016(2) -.008(2) -.008(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_thermal_displace_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_group _atom_site_type_symbol O1 .3083(5) .6944(3) -.2649(2) .0874(9) Uani d . 1 . O O2 .2033(5) .5725(3) -.1002(2) .0883(10) Uani d . 1 . O N1 .2658(4) .5679(4) -.2040(2) .0562(7) Uani d . 1 . N N2 .2488(4) .2286(3) -.0713(2) .0495(7) Uani d . 1 . N H2a .2288(4) .3225(3) -.0344(2) .080 Uiso d R 1 . H N3 .2477(4) .0702(3) -.0127(2) .0463(7) Uani d . 1 . N N4 .2169(4) .0749(3) .0928(2) .0518(7) Uani d . 1 . N N5 .1155(6) .1816(5) .3704(3) .0952(12) Uani d . 1 . N C1 .2831(4) .2480(4) -.1885(2) .0402(7) Uani d . 1 . C C2 .2911(4) .4098(4) -.2553(2) .0429(7) Uani d . 1 . C C3 .3264(5) .4244(4) -.3731(3) .0516(8) Uani d . 1 . C H3 .3310(5) .5365(4) -.4171(3) .080 Uiso d R 1 . H C4 .3542(5) .2809(4) -.4278(3) .0565(9) Uani d . 1 . C H4 .3799(5) .2912(4) -.5093(3) .080 Uiso d R 1 . H C5 .3464(5) .1190(4) -.3631(3) .0553(9) Uani d . 1 . C H5 .3648(5) .0184(4) -.4012(3) .080 Uiso d R 1 . H C6 .3139(5) .1017(4) -.2468(3) .0495(8) Uani d . 1 . C H6 .3096(5) -.0111(4) -.2040(3) .080 Uiso d R 1 . H C7 .2128(5) -.0914(4) .1567(2) .0459(8) Uani d . 1 . C C8 .1724(5) -.0952(4) .2751(3) .0476(8) Uani d . 1 . C C9 .1613(5) -.2514(4) .3447(3) .0563(9) Uani d . 1 . C H9 .1352(5) -.2532(4) .4258(3) .080 Uiso d R 1 . H C10 .1906(5) -.4028(5) .2980(3) .0618(9) Uani d . 1 . C H10 .1793(5) -.5098(5) .3466(3) .080 Uiso d R 1 . H C11 .2325(6) -.4011(4) .1813(3) .0625(10) Uani d . 1 . C H11 .2538(6) -.5083(4) .1492(3) .080 Uiso d R 1 . H C12 .2428(5) -.2470(4) .1107(3) .0553(9) Uani d . 1 . C H12 .2725(5) -.2468(4) .0296(3) .080 Uiso d R 1 . H C13 .1418(5) .0627(5) .3260(3) .0544(9) Uani d . 1 . C 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' O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 2 1 1 -2 0 -2 -1 2 0 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 O1 N1 O2 121.0(3) yes O1 N1 C2 119.0(3) yes O2 N1 C2 120.0(3) yes N3 N2 C1 120.1(2) yes N4 N3 N2 112.0(2) yes N3 N4 C7 113.0(2) yes N2 C1 C2 122.9(3) yes N2 C1 C6 120.2(3) yes C2 C1 C6 116.9(3) ? C3 C2 C1 121.4(3) ? C3 C2 N1 117.1(3) yes C1 C2 N1 121.5(3) yes C4 C3 C2 120.6(3) ? C3 C4 C5 118.9(3) ? C6 C5 C4 121.2(3) ? C5 C6 C1 120.9(3) ? C12 C7 C8 118.6(3) yes C12 C7 N4 125.0(3) yes C8 C7 N4 116.4(3) ? C9 C8 C7 120.4(3) ? C9 C8 C13 119.4(3) ? C7 C8 C13 120.2(3) ? C10 C9 C8 120.2(3) ? C9 C10 C11 119.9(3) ? C10 C11 C12 120.9(3) ? C11 C12 C7 120.1(3) ? C5 C2 N1 177.0(2) yes N5 C13 C8 176.7(4) yes N1 O2 H2a 106 yes 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 O1 N1 . 1.220(3) yes O2 N1 . 1.235(3) yes N1 C2 . 1.453(4) yes N2 N3 . 1.337(3) yes N2 C1 . 1.380(4) yes N3 N4 . 1.258(3) yes N4 C7 . 1.418(4) yes N5 C13 . 1.119(4) yes C1 C2 . 1.407(4) yes C1 C6 . 1.408(4) yes C2 C3 . 1.389(4) yes C3 C4 . 1.367(4) yes C4 C5 . 1.397(4) yes C5 C6 . 1.370(4) yes C7 C12 . 1.390(4) yes C7 C8 . 1.399(4) yes C8 C9 . 1.389(4) yes C8 C13 . 1.438(5) yes C9 C10 . 1.364(5) yes C10 C11 . 1.380(5) yes C11 C12 . 1.380(4) yes 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 N2 H2a O2 . .90 1.98 2.622(3) 128 C5 H5 O1 1_545 .96 2.90 3.468(4) 119 C6 H6 O1 1_545 .96 2.61 3.327(4) 132 C9 H9 N5 2_556 .96 2.70 3.573(5) 152 C10 H10 N5 1_545 .96 2.62 3.473(5) 148 C11 H11 O2 1_545 .96 3.09 3.562(5) 112 C12 H12 O2 1_545 .96 2.58 3.308(4) 133 loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 240623 2 PubChem 135478652