#------------------------------------------------------------------------------ #$Date: 2022-05-22 15:40:46 +0300 (Sun, 22 May 2022) $ #$Revision: 275611 $ #$URL: file:///home/coder/svn-repositories/cod/cif/4/03/89/4038997.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_4038997 loop_ _publ_author_name 'Numez Avila, Aaron Gabriel' 'Desch\^enes-Simard, Beno\^it' 'Arnold, Joseph E.' 'Morency, Mathieu' 'Chartrand, Daniel' 'Maris, Thierry' 'Berger, Gilles' 'Day, Graham M.' 'Hanessian, Stephen' 'Wuest, James D.' _publ_contact_author_id_orcid 0000-0001-9731-4046 _publ_section_title ; Surprising Chemistry of 6.Azidotetrazolo[5,1.a]phthalazine: What a Purported Natural Product Reveals about the Polymorphism of Explosives ; _journal_name_full 'Journal of Organic Chemistry' _journal_page_first 6680 _journal_page_last 6694 _journal_paper_doi 10.1021/acs.joc.2c00369 _journal_volume 87 _journal_year 2022 _chemical_formula_moiety 'C8 H4 N8' _chemical_formula_sum 'C8 H4 N8' _chemical_formula_weight 212.19 _space_group_crystal_system monoclinic _space_group_IT_number 4 _space_group_name_Hall 'P 2yb' _space_group_name_H-M_alt 'P 1 21 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_contact_author_email thierry.maris@umontreal.ca _audit_contact_author_name 'Thierry Maris' _audit_contact_author_phone '+1 514 340 4711 2579' _audit_creation_date 2021-02-04 _audit_creation_method ; Olex2 1.3 (compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226) ; _cell_angle_alpha 90 _cell_angle_beta 104.155(1) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 7.4796(2) _cell_length_b 5.1345(1) _cell_length_c 11.9958(3) _cell_measurement_reflns_used 5066 _cell_measurement_temperature 100 _cell_measurement_theta_max 70.111 _cell_measurement_theta_min 3.800 _cell_volume 446.699(19) _computing_cell_refinement ; SAINT (2013) V8.40B; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173. ; _computing_data_collection ; APEX 3 (2019) Bruker AXS Inc., Madison, WI 53719-1173. ; _computing_data_reduction ; SAINT (2013) V8.40B; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173. ; _computing_molecular_graphics 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_structure_refinement 'XL (Sheldrick, 2008)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_temperature 100 _diffrn_detector 'CCD area detector' _diffrn_detector_area_resol_mean 8.3 _diffrn_detector_type 'Bruker APEX2 CCD' _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device 'three-circle diffractometer' _diffrn_measurement_device_type 'Bruker Smart APEX' _diffrn_measurement_method '\w scans' _diffrn_radiation_collimation 'Focusing mirrors' _diffrn_radiation_monochromator 'Quazar MX Mirror Optics' _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0345 _diffrn_reflns_av_unetI/netI 0.0273 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 1.000 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 6039 _diffrn_reflns_point_group_measured_fraction_full 0.988 _diffrn_reflns_point_group_measured_fraction_max 0.986 _diffrn_reflns_theta_full 67.679 _diffrn_reflns_theta_max 70.105 _diffrn_reflns_theta_min 3.800 _diffrn_source 'Microfocus Source' _diffrn_source_current 20.0 _diffrn_source_power 0.8 _diffrn_source_target Cu _diffrn_source_type 'Incoatec I\mS High Brilliance Microsource' _diffrn_source_voltage 40.0 _exptl_absorpt_coefficient_mu 0.943 _exptl_absorpt_correction_T_max 0.7533 _exptl_absorpt_correction_T_min 0.5896 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1010 before and 0.0483 after correction. The Ratio of minimum to maximum transmission is 0.7827. The \l/2 correction factor is Not present. ; _exptl_crystal_colour 'clear light colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.578 _exptl_crystal_description Block _exptl_crystal_F_000 216 _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.16 _refine_diff_density_max 0.177 _refine_diff_density_min -0.260 _refine_diff_density_rms 0.054 _refine_ls_abs_structure_details ; Flack x determined using 706 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack -0.2(3) _refine_ls_extinction_coef 0.052(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2018/3 (Sheldrick 2018)' _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 146 _refine_ls_number_reflns 1674 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.064 _refine_ls_R_factor_all 0.0359 _refine_ls_R_factor_gt 0.0358 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0679P)^2^+0.0251P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0904 _refine_ls_wR_factor_ref 0.0907 _reflns_Friedel_coverage 0.762 _reflns_Friedel_fraction_full 0.973 _reflns_Friedel_fraction_max 0.969 _reflns_number_gt 1656 _reflns_number_total 1674 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file bent61.cif _cod_data_source_block bent61 _cod_database_code 4038997 loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y+1/2, -z' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group N1 N -0.0034(2) -0.6755(4) -0.18361(14) 0.0367(4) Uani 1 1 d . . . . . N2 N 0.0202(2) -0.8825(4) -0.25007(15) 0.0396(5) Uani 1 1 d . . . . . N3 N -0.1315(2) -0.9446(4) -0.32497(14) 0.0351(4) Uani 1 1 d . . . . . N4 N -0.2586(2) -0.7735(3) -0.30714(12) 0.0287(4) Uani 1 1 d . . . . . N5 N -0.4363(2) -0.7793(3) -0.37088(12) 0.0294(4) Uani 1 1 d . . . . . N6 N -0.7264(2) -0.5887(3) -0.39593(13) 0.0331(4) Uani 1 1 d . . . . . N7 N -0.7839(2) -0.7807(4) -0.45974(13) 0.0329(4) Uani 1 1 d . . . . . N8 N -0.8551(3) -0.9413(4) -0.51778(16) 0.0411(5) Uani 1 1 d . . . . . C1 C -0.1794(2) -0.6105(4) -0.22053(14) 0.0293(4) Uani 1 1 d . . . . . C2 C -0.2930(2) -0.4159(4) -0.18617(14) 0.0286(4) Uani 1 1 d . . . . . C3 C -0.2286(3) -0.2418(4) -0.09535(15) 0.0324(4) Uani 1 1 d . . . . . H3 H -0.105961 -0.245251 -0.054047 0.039 Uiso 1 1 calc R U . . . C4 C -0.3507(3) -0.0645(4) -0.06816(16) 0.0359(5) Uani 1 1 d . . . . . H4 H -0.309393 0.052623 -0.008237 0.043 Uiso 1 1 calc R U . . . C5 C -0.5351(3) -0.0592(4) -0.12955(16) 0.0340(4) Uani 1 1 d . . . . . H5 H -0.614997 0.061926 -0.110265 0.041 Uiso 1 1 calc R U . . . C6 C -0.6003(3) -0.2316(4) -0.21859(15) 0.0310(4) Uani 1 1 d . . . . . H6 H -0.723583 -0.227629 -0.258734 0.037 Uiso 1 1 calc R U . . . C7 C -0.4791(3) -0.4126(4) -0.24793(15) 0.0275(4) Uani 1 1 d . . . . . C8 C -0.5396(3) -0.6021(4) -0.33988(14) 0.0280(4) Uani 1 1 d . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0269(8) 0.0471(10) 0.0354(8) 0.0039(7) 0.0063(6) 0.0061(7) N2 0.0302(9) 0.0486(11) 0.0411(8) 0.0064(8) 0.0107(7) 0.0113(8) N3 0.0322(9) 0.0382(9) 0.0377(8) 0.0031(7) 0.0142(7) 0.0108(7) N4 0.0245(7) 0.0335(8) 0.0289(7) 0.0029(6) 0.0079(6) 0.0057(7) N5 0.0264(7) 0.0339(8) 0.0285(7) 0.0005(6) 0.0077(6) 0.0016(7) N6 0.0256(8) 0.0385(9) 0.0340(7) -0.0054(7) 0.0048(6) 0.0015(7) N7 0.0252(7) 0.0398(9) 0.0335(8) -0.0010(7) 0.0070(6) 0.0018(7) N8 0.0331(9) 0.0442(10) 0.0440(9) -0.0068(9) 0.0054(7) -0.0021(8) C1 0.0271(9) 0.0357(10) 0.0257(8) 0.0042(7) 0.0073(7) 0.0019(8) C2 0.0276(9) 0.0332(10) 0.0265(9) 0.0052(8) 0.0091(7) 0.0013(8) C3 0.0310(9) 0.0376(10) 0.0281(8) 0.0013(8) 0.0065(7) -0.0016(8) C4 0.0450(11) 0.0347(10) 0.0294(8) -0.0024(8) 0.0116(8) -0.0031(9) C5 0.0395(10) 0.0319(9) 0.0350(9) 0.0009(8) 0.0175(8) 0.0041(9) C6 0.0290(9) 0.0336(10) 0.0323(9) 0.0042(8) 0.0110(7) 0.0048(8) C7 0.0273(9) 0.0305(9) 0.0259(8) 0.0029(7) 0.0091(7) 0.0002(7) C8 0.0255(9) 0.0318(9) 0.0277(8) 0.0029(8) 0.0083(7) 0.0009(7) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 '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_site_symmetry_1 _geom_angle_site_symmetry_3 C1 N1 N2 105.11(17) . . N3 N2 N1 112.20(17) . . N2 N3 N4 105.07(16) . . N3 N4 N5 121.70(15) . . N3 N4 C1 109.32(15) . . C1 N4 N5 128.97(16) . . C8 N5 N4 112.89(16) . . N7 N6 C8 114.03(16) . . N8 N7 N6 172.00(19) . . N1 C1 N4 108.30(17) . . N1 C1 C2 133.52(18) . . N4 C1 C2 118.17(16) . . C3 C2 C1 123.54(17) . . C3 C2 C7 120.61(17) . . C7 C2 C1 115.82(16) . . C2 C3 H3 120.6 . . C4 C3 C2 118.83(17) . . C4 C3 H3 120.6 . . C3 C4 H4 119.6 . . C3 C4 C5 120.82(18) . . C5 C4 H4 119.6 . . C4 C5 H5 119.6 . . C6 C5 C4 120.81(18) . . C6 C5 H5 119.6 . . C5 C6 H6 120.3 . . C5 C6 C7 119.40(17) . . C7 C6 H6 120.3 . . C2 C7 C8 118.32(16) . . C6 C7 C2 119.53(17) . . C6 C7 C8 122.15(17) . . N5 C8 N6 119.30(17) . . N5 C8 C7 125.81(17) . . N6 C8 C7 114.87(16) . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 N1 N2 1.366(2) . N1 C1 1.324(2) . N2 N3 1.303(3) . N3 N4 1.349(2) . N4 N5 1.362(2) . N4 C1 1.353(2) . N5 C8 1.305(2) . N6 N7 1.257(2) . N6 C8 1.397(2) . N7 N8 1.126(3) . C1 C2 1.436(3) . C2 C3 1.401(3) . C2 C7 1.408(2) . C3 H3 0.9300 . C3 C4 1.384(3) . C4 H4 0.9300 . C4 C5 1.396(3) . C5 H5 0.9300 . C5 C6 1.381(3) . C6 H6 0.9300 . C6 C7 1.402(3) . C7 C8 1.457(3) . 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 N1 N2 N3 N4 0.0(2) . . . . N1 C1 C2 C3 -0.8(3) . . . . N1 C1 C2 C7 -179.12(19) . . . . N2 N1 C1 N4 -0.3(2) . . . . N2 N1 C1 C2 178.44(19) . . . . N2 N3 N4 N5 179.91(15) . . . . N2 N3 N4 C1 -0.1(2) . . . . N3 N4 N5 C8 178.88(17) . . . . N3 N4 C1 N1 0.3(2) . . . . N3 N4 C1 C2 -178.68(15) . . . . N4 N5 C8 N6 -178.50(15) . . . . N4 N5 C8 C7 0.2(3) . . . . N4 C1 C2 C3 177.81(17) . . . . N4 C1 C2 C7 -0.5(2) . . . . N5 N4 C1 N1 -179.78(16) . . . . N5 N4 C1 C2 1.3(3) . . . . N7 N6 C8 N5 11.2(2) . . . . N7 N6 C8 C7 -167.63(16) . . . . C1 N1 N2 N3 0.2(2) . . . . C1 N4 N5 C8 -1.1(3) . . . . C1 C2 C3 C4 -178.93(17) . . . . C1 C2 C7 C6 178.90(16) . . . . C1 C2 C7 C8 -0.2(2) . . . . C2 C3 C4 C5 0.3(3) . . . . C2 C7 C8 N5 0.4(3) . . . . C2 C7 C8 N6 179.14(15) . . . . C3 C2 C7 C6 0.5(3) . . . . C3 C2 C7 C8 -178.60(16) . . . . C3 C4 C5 C6 0.3(3) . . . . C4 C5 C6 C7 -0.5(3) . . . . C5 C6 C7 C2 0.1(3) . . . . C5 C6 C7 C8 179.14(16) . . . . C6 C7 C8 N5 -178.68(17) . . . . C6 C7 C8 N6 0.0(3) . . . . C7 C2 C3 C4 -0.7(3) . . . . _cod_database_fobs_code 4038997