#------------------------------------------------------------------------------ #$Date: 2022-05-22 15:40:35 +0300 (Sun, 22 May 2022) $ #$Revision: 275610 $ #$URL: file:///home/coder/svn-repositories/cod/cif/4/03/89/4038996.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_4038996 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 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 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 102.164(1) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 6.1658(1) _cell_length_b 17.1862(3) _cell_length_c 8.8111(2) _cell_measurement_reflns_used 7128 _cell_measurement_temperature 100 _cell_measurement_theta_max 72.094 _cell_measurement_theta_min 5.147 _cell_volume 912.72(3) _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 Smart CCD 6000 Area Detector' _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_device 'three-circle diffractometer' _diffrn_measurement_device_type 'Bruker Smart 6000' _diffrn_measurement_method '\w scans' _diffrn_radiation_collimation 'Focusing mirrors' _diffrn_radiation_monochromator 'Montel 200 Mirrors Optics' _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0339 _diffrn_reflns_av_unetI/netI 0.0211 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.997 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_number 11709 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.997 _diffrn_reflns_theta_full 67.679 _diffrn_reflns_theta_max 72.094 _diffrn_reflns_theta_min 5.147 _diffrn_source 'Rotating Anode' _diffrn_source_current 20.0 _diffrn_source_power 0.8 _diffrn_source_target Cu _diffrn_source_type 'Nonius FR591 Rotating Anode' _diffrn_source_voltage 40.0 _exptl_absorpt_coefficient_mu 0.923 _exptl_absorpt_correction_T_max 0.7536 _exptl_absorpt_correction_T_min 0.6610 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0730 before and 0.0476 after correction. The Ratio of minimum to maximum transmission is 0.8771. 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 1.544 _exptl_crystal_description plate _exptl_crystal_F_000 432 _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.232 _refine_diff_density_min -0.389 _refine_diff_density_rms 0.080 _refine_ls_extinction_coef 0.025(2) _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 1.068 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 146 _refine_ls_number_reflns 1797 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.068 _refine_ls_R_factor_all 0.0445 _refine_ls_R_factor_gt 0.0429 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0721P)^2^+0.1450P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1071 _refine_ls_wR_factor_ref 0.1094 _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 1676 _reflns_number_total 1797 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file bent35.cif _cod_data_source_block bent35 _cod_database_code 4038996 loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x, -y-1/2, z-1/2' 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 0.82532(16) 0.73064(5) 0.57063(12) 0.0318(3) Uani 1 1 d . . . . . N2 N 0.86316(16) 0.80807(6) 0.55394(12) 0.0329(3) Uani 1 1 d . . . . . N3 N 0.73396(15) 0.85141(6) 0.61765(11) 0.0307(3) Uani 1 1 d . . . . . N4 N 0.60759(14) 0.80093(5) 0.67798(10) 0.0260(3) Uani 1 1 d . . . . . N5 N 0.44745(15) 0.82562(5) 0.75281(11) 0.0274(3) Uani 1 1 d . . . . . N6 N 0.17545(17) 0.78502(5) 0.88298(11) 0.0314(3) Uani 1 1 d . . . . . N7 N 0.13938(15) 0.85630(6) 0.89796(11) 0.0321(3) Uani 1 1 d . . . . . N8 N 0.0879(2) 0.91691(6) 0.92106(14) 0.0442(3) Uani 1 1 d . . . . . C1 C 0.66495(18) 0.72728(6) 0.64972(12) 0.0270(3) Uani 1 1 d . . . . . C2 C 0.55091(18) 0.66438(6) 0.70582(13) 0.0277(3) Uani 1 1 d . . . . . C3 C 0.6007(2) 0.58573(7) 0.68881(15) 0.0349(3) Uani 1 1 d . . . . . H3 H 0.712049 0.571406 0.637724 0.042 Uiso 1 1 calc R U . . . C4 C 0.4820(2) 0.52991(7) 0.74902(16) 0.0404(3) Uani 1 1 d . . . . . H4 H 0.514709 0.477584 0.738922 0.048 Uiso 1 1 calc R U . . . C5 C 0.3134(2) 0.55078(7) 0.82492(14) 0.0376(3) Uani 1 1 d . . . . . H5 H 0.234990 0.512188 0.864300 0.045 Uiso 1 1 calc R U . . . C6 C 0.26157(19) 0.62812(7) 0.84229(14) 0.0320(3) Uani 1 1 d . . . . . H6 H 0.148785 0.641679 0.892655 0.038 Uiso 1 1 calc R U . . . C7 C 0.38124(18) 0.68571(6) 0.78299(12) 0.0265(3) Uani 1 1 d . . . . . C8 C 0.34136(18) 0.76838(6) 0.80132(12) 0.0260(3) 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 0.0314(5) 0.0302(5) 0.0364(5) -0.0015(4) 0.0134(4) -0.0006(4) N2 0.0313(5) 0.0329(5) 0.0369(5) 0.0007(4) 0.0126(4) -0.0018(4) N3 0.0309(5) 0.0281(5) 0.0350(5) 0.0020(4) 0.0111(4) -0.0038(4) N4 0.0273(5) 0.0228(5) 0.0293(5) 0.0001(3) 0.0092(4) -0.0010(4) N5 0.0289(5) 0.0239(5) 0.0313(5) -0.0010(4) 0.0107(4) 0.0010(4) N6 0.0363(5) 0.0240(5) 0.0380(5) -0.0017(4) 0.0171(4) 0.0006(4) N7 0.0326(5) 0.0305(6) 0.0350(5) -0.0032(4) 0.0113(4) 0.0005(4) N8 0.0476(6) 0.0323(6) 0.0545(7) -0.0084(5) 0.0149(5) 0.0067(5) C1 0.0275(5) 0.0252(6) 0.0283(5) -0.0022(4) 0.0060(4) 0.0013(4) C2 0.0297(6) 0.0248(6) 0.0291(5) -0.0003(4) 0.0073(4) -0.0006(4) C3 0.0378(6) 0.0267(6) 0.0421(7) -0.0027(5) 0.0131(5) 0.0037(5) C4 0.0504(7) 0.0211(6) 0.0508(7) 0.0002(5) 0.0132(6) 0.0024(5) C5 0.0441(7) 0.0253(6) 0.0447(7) 0.0042(5) 0.0125(5) -0.0052(5) C6 0.0346(6) 0.0287(6) 0.0343(6) 0.0013(5) 0.0107(4) -0.0026(5) C7 0.0285(5) 0.0239(6) 0.0272(5) -0.0001(4) 0.0060(4) -0.0001(4) C8 0.0277(5) 0.0249(6) 0.0259(5) 0.0001(4) 0.0068(4) 0.0000(4) 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 105.22(9) . . N3 N2 N1 112.19(9) . . N2 N3 N4 105.01(9) . . N3 N4 N5 121.83(9) . . N3 N4 C1 109.56(9) . . C1 N4 N5 128.61(10) . . C8 N5 N4 112.84(9) . . N7 N6 C8 114.71(10) . . N8 N7 N6 171.36(12) . . N1 C1 N4 108.02(9) . . N1 C1 C2 133.52(10) . . N4 C1 C2 118.46(10) . . C3 C2 C1 123.80(11) . . C3 C2 C7 120.23(11) . . C7 C2 C1 115.96(10) . . C2 C3 H3 120.5 . . C4 C3 C2 118.95(11) . . C4 C3 H3 120.5 . . C3 C4 H4 119.5 . . C3 C4 C5 120.97(11) . . C5 C4 H4 119.5 . . C4 C5 H5 119.6 . . C6 C5 C4 120.84(11) . . C6 C5 H5 119.6 . . C5 C6 H6 120.5 . . C5 C6 C7 119.07(11) . . C7 C6 H6 120.5 . . C2 C7 C8 117.80(11) . . C6 C7 C2 119.93(11) . . C6 C7 C8 122.25(10) . . N5 C8 N6 119.13(10) . . N5 C8 C7 126.31(10) . . N6 C8 C7 114.54(10) . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 N1 N2 1.3644(14) . N1 C1 1.3255(15) . N2 N3 1.3012(14) . N3 N4 1.3479(13) . N4 N5 1.3653(13) . N4 C1 1.3514(14) . N5 C8 1.3023(14) . N6 N7 1.2570(14) . N6 C8 1.3986(14) . N7 N8 1.1200(14) . C1 C2 1.4331(15) . C2 C3 1.4011(15) . C2 C7 1.4110(16) . C3 H3 0.9300 . C3 C4 1.3788(18) . C4 H4 0.9300 . C4 C5 1.3961(18) . C5 H5 0.9300 . C5 C6 1.3832(17) . C6 H6 0.9300 . C6 C7 1.3997(16) . C7 C8 1.4568(15) . 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 0.01(12) . . . . N1 C1 C2 C3 2.5(2) . . . . N1 C1 C2 C7 -178.09(12) . . . . N2 N1 C1 N4 0.56(12) . . . . N2 N1 C1 C2 -179.50(11) . . . . N2 N3 N4 N5 -178.87(9) . . . . N2 N3 N4 C1 0.35(11) . . . . N3 N4 N5 C8 179.25(9) . . . . N3 N4 C1 N1 -0.58(12) . . . . N3 N4 C1 C2 179.47(9) . . . . N4 N5 C8 N6 178.69(9) . . . . N4 N5 C8 C7 0.45(16) . . . . N4 C1 C2 C3 -177.61(10) . . . . N4 C1 C2 C7 1.84(15) . . . . N5 N4 C1 N1 178.57(10) . . . . N5 N4 C1 C2 -1.38(17) . . . . N7 N6 C8 N5 2.10(15) . . . . N7 N6 C8 C7 -179.47(9) . . . . C1 N1 N2 N3 -0.36(12) . . . . C1 N4 N5 C8 0.19(16) . . . . C1 C2 C3 C4 179.21(11) . . . . C1 C2 C7 C6 -179.72(10) . . . . C1 C2 C7 C8 -1.30(15) . . . . C2 C3 C4 C5 0.5(2) . . . . C2 C7 C8 N5 0.15(17) . . . . C2 C7 C8 N6 -178.15(9) . . . . C3 C2 C7 C6 -0.25(17) . . . . C3 C2 C7 C8 178.18(10) . . . . C3 C4 C5 C6 -0.3(2) . . . . C4 C5 C6 C7 -0.21(18) . . . . C5 C6 C7 C2 0.46(17) . . . . C5 C6 C7 C8 -177.89(10) . . . . C6 C7 C8 N5 178.54(10) . . . . C6 C7 C8 N6 0.23(15) . . . . C7 C2 C3 C4 -0.22(18) . . . . _cod_database_fobs_code 4038996