#------------------------------------------------------------------------------ #$Date: 2022-05-22 15:40:23 +0300 (Sun, 22 May 2022) $ #$Revision: 275609 $ #$URL: file:///home/coder/svn-repositories/cod/cif/4/03/89/4038995.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_4038995 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_absolute_configuration unk _chemical_formula_moiety 'C8 H4 N8' _chemical_formula_sum 'C8 H4 N8' _chemical_formula_weight 212.19 _space_group_crystal_system orthorhombic _space_group_IT_number 43 _space_group_name_Hall 'F 2 -2d' _space_group_name_H-M_alt 'F d d 2' _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 90 _cell_angle_gamma 90 _cell_formula_units_Z 16 _cell_length_a 20.2505(10) _cell_length_b 33.1064(15) _cell_length_c 5.3773(3) _cell_measurement_reflns_used 3304 _cell_measurement_temperature 100 _cell_measurement_theta_max 69.587 _cell_measurement_theta_min 5.120 _cell_volume 3605.1(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 0.998 _diffrn_measured_fraction_theta_max 0.998 _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 0.0439 _diffrn_reflns_av_unetI/netI 0.0275 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_k_max 40 _diffrn_reflns_limit_k_min -40 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_number 11750 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_theta_full 67.679 _diffrn_reflns_theta_max 72.268 _diffrn_reflns_theta_min 5.120 _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 0.935 _exptl_absorpt_correction_T_max 0.7536 _exptl_absorpt_correction_T_min 0.6077 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0997 before and 0.0617 after correction. The Ratio of minimum to maximum transmission is 0.8064. 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 1.564 _exptl_crystal_description needle _exptl_crystal_F_000 1728 _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.04 _refine_diff_density_max 0.171 _refine_diff_density_min -0.209 _refine_diff_density_rms 0.050 _refine_ls_abs_structure_details ; Refined as an inversion twin. ; _refine_ls_abs_structure_Flack 0.0(6) _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 146 _refine_ls_number_reflns 1776 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.061 _refine_ls_R_factor_all 0.0404 _refine_ls_R_factor_gt 0.0367 _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^)+(0.0608P)^2^+0.2833P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0908 _refine_ls_wR_factor_ref 0.0934 _reflns_Friedel_coverage 0.799 _reflns_Friedel_fraction_full 1.000 _reflns_Friedel_fraction_max 1.000 _reflns_number_gt 1632 _reflns_number_total 1776 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file bent33.cif _cod_data_source_block bent33 _cod_database_code 4038995 loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, z' 3 'x+1/4, -y+1/4, z+1/4' 4 '-x+1/4, y+1/4, z+1/4' 5 'x, y+1/2, z+1/2' 6 '-x, -y+1/2, z+1/2' 7 'x+1/4, -y+3/4, z+3/4' 8 '-x+1/4, y+3/4, z+3/4' 9 'x+1/2, y, z+1/2' 10 '-x+1/2, -y, z+1/2' 11 'x+3/4, -y+1/4, z+3/4' 12 '-x+3/4, y+1/4, z+3/4' 13 'x+1/2, y+1/2, z' 14 '-x+1/2, -y+1/2, z' 15 'x+3/4, -y+3/4, z+1/4' 16 '-x+3/4, y+3/4, z+1/4' 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 0.67312(11) 0.62868(6) 0.9541(4) 0.0466(5) Uani 1 1 d . . . . . N2 N 0.67778(11) 0.58792(7) 0.9869(5) 0.0502(5) Uani 1 1 d . . . . . N3 N 0.64389(11) 0.56790(7) 0.8200(5) 0.0472(5) Uani 1 1 d . . . . . N4 N 0.61653(10) 0.59657(6) 0.6743(4) 0.0398(5) Uani 1 1 d . . . . . N5 N 0.57733(10) 0.58673(6) 0.4772(4) 0.0409(5) Uani 1 1 d . . . . . N6 N 0.51583(11) 0.61301(6) 0.1491(4) 0.0467(6) Uani 1 1 d . . . . . N7 N 0.50535(10) 0.57695(6) 0.0880(5) 0.0477(5) Uani 1 1 d . . . . . N8 N 0.49145(13) 0.54687(8) 0.0077(5) 0.0613(7) Uani 1 1 d . . . . . C1 C 0.63438(11) 0.63340(7) 0.7569(5) 0.0388(6) Uani 1 1 d . . . . . C2 C 0.60984(12) 0.66839(7) 0.6269(5) 0.0385(6) Uani 1 1 d . . . . . C3 C 0.62444(13) 0.70823(7) 0.6945(5) 0.0437(6) Uani 1 1 d . . . . . H3 H 0.651051 0.713705 0.835994 0.052 Uiso 1 1 calc R U . . . C4 C 0.59969(13) 0.73931(7) 0.5529(6) 0.0468(6) Uani 1 1 d . . . . . H4 H 0.609803 0.766441 0.595945 0.056 Uiso 1 1 calc R U . . . C5 C 0.56008(12) 0.73152(7) 0.3476(6) 0.0457(6) Uani 1 1 d . . . . . H5 H 0.543279 0.753403 0.252409 0.055 Uiso 1 1 calc R U . . . C6 C 0.54480(13) 0.69244(7) 0.2802(5) 0.0428(6) Uani 1 1 d . . . . . H6 H 0.517418 0.687405 0.140118 0.051 Uiso 1 1 calc R U . . . C7 C 0.56996(11) 0.66028(7) 0.4196(5) 0.0382(5) Uani 1 1 d . . . . . C8 C 0.55611(11) 0.61826(7) 0.3575(5) 0.0382(5) 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 0.0450(11) 0.0515(12) 0.0434(12) 0.0052(10) 0.0038(10) 0.0030(9) N2 0.0487(12) 0.0526(12) 0.0494(13) 0.0107(11) 0.0039(10) 0.0084(10) N3 0.0479(12) 0.0447(11) 0.0491(13) 0.0069(10) 0.0052(10) 0.0094(9) N4 0.0410(10) 0.0372(10) 0.0412(11) 0.0050(9) 0.0071(9) 0.0044(8) N5 0.0423(11) 0.0375(10) 0.0428(12) 0.0003(9) 0.0062(9) 0.0013(8) N6 0.0494(12) 0.0385(11) 0.0523(15) -0.0005(10) -0.0003(10) -0.0052(9) N7 0.0442(12) 0.0452(13) 0.0536(12) -0.0030(10) 0.0070(10) -0.0052(9) N8 0.0622(15) 0.0494(14) 0.0724(17) -0.0100(13) 0.0039(13) -0.0107(11) C1 0.0367(12) 0.0419(12) 0.0378(14) 0.0004(11) 0.0082(10) 0.0020(9) C2 0.0365(12) 0.0396(13) 0.0394(13) 0.0016(10) 0.0099(10) 0.0024(9) C3 0.0467(14) 0.0416(13) 0.0429(14) -0.0042(11) 0.0059(11) -0.0012(10) C4 0.0522(15) 0.0349(12) 0.0531(15) -0.0019(11) 0.0081(12) -0.0017(10) C5 0.0505(14) 0.0385(13) 0.0481(14) 0.0046(12) 0.0071(12) 0.0041(11) C6 0.0427(12) 0.0437(13) 0.0419(14) 0.0018(11) 0.0048(11) 0.0012(10) C7 0.0373(12) 0.0369(12) 0.0404(13) -0.0005(10) 0.0106(10) 0.0001(9) C8 0.0366(12) 0.0389(12) 0.0390(13) 0.0013(11) 0.0088(10) -0.0004(9) 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 105.1(2) . . N3 N2 N1 112.1(2) . . N2 N3 N4 104.9(2) . . N3 N4 N5 121.5(2) . . C1 N4 N3 109.6(2) . . C1 N4 N5 129.0(2) . . C8 N5 N4 112.7(2) . . N7 N6 C8 115.3(2) . . N8 N7 N6 170.8(3) . . N1 C1 N4 108.4(2) . . N1 C1 C2 133.3(2) . . N4 C1 C2 118.4(2) . . C3 C2 C1 124.0(2) . . C3 C2 C7 120.6(2) . . C7 C2 C1 115.5(2) . . C2 C3 H3 120.5 . . C4 C3 C2 119.0(3) . . C4 C3 H3 120.5 . . C3 C4 H4 119.6 . . C3 C4 C5 120.8(2) . . C5 C4 H4 119.6 . . C4 C5 H5 119.6 . . C6 C5 C4 120.9(3) . . C6 C5 H5 119.6 . . C5 C6 H6 120.3 . . C5 C6 C7 119.5(3) . . C7 C6 H6 120.3 . . C2 C7 C8 118.4(2) . . C6 C7 C2 119.4(2) . . C6 C7 C8 122.2(2) . . N5 C8 N6 119.4(2) . . N5 C8 C7 126.1(2) . . N6 C8 C7 114.5(2) . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 N1 N2 1.364(3) . N1 C1 1.328(3) . N2 N3 1.310(4) . N3 N4 1.350(3) . N4 N5 1.363(3) . N4 C1 1.347(3) . N5 C8 1.300(3) . N6 N7 1.256(3) . N6 C8 1.397(3) . N7 N8 1.121(3) . C1 C2 1.441(3) . C2 C3 1.400(3) . C2 C7 1.402(4) . C3 H3 0.9500 . C3 C4 1.375(4) . C4 H4 0.9500 . C4 C5 1.389(4) . C5 H5 0.9500 . C5 C6 1.379(3) . C6 H6 0.9500 . C6 C7 1.399(3) . C7 C8 1.458(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 0.1(3) . . . . N1 C1 C2 C3 0.1(4) . . . . N1 C1 C2 C7 179.1(2) . . . . N2 N1 C1 N4 -0.1(3) . . . . N2 N1 C1 C2 179.6(2) . . . . N2 N3 N4 N5 179.9(2) . . . . N2 N3 N4 C1 -0.1(3) . . . . N3 N4 N5 C8 -179.3(2) . . . . N3 N4 C1 N1 0.1(3) . . . . N3 N4 C1 C2 -179.6(2) . . . . N4 N5 C8 N6 179.4(2) . . . . N4 N5 C8 C7 -0.9(3) . . . . N4 C1 C2 C3 179.7(2) . . . . N4 C1 C2 C7 -1.3(3) . . . . N5 N4 C1 N1 -179.9(2) . . . . N5 N4 C1 C2 0.4(3) . . . . N7 N6 C8 N5 -2.7(3) . . . . N7 N6 C8 C7 177.6(2) . . . . C1 N1 N2 N3 0.0(3) . . . . C1 N4 N5 C8 0.7(3) . . . . C1 C2 C3 C4 178.3(2) . . . . C1 C2 C7 C6 -179.0(2) . . . . C1 C2 C7 C8 1.1(3) . . . . C2 C3 C4 C5 0.8(4) . . . . C2 C7 C8 N5 0.1(3) . . . . C2 C7 C8 N6 179.8(2) . . . . C3 C2 C7 C6 0.0(3) . . . . C3 C2 C7 C8 -179.9(2) . . . . C3 C4 C5 C6 -0.3(4) . . . . C4 C5 C6 C7 -0.4(4) . . . . C5 C6 C7 C2 0.5(3) . . . . C5 C6 C7 C8 -179.6(2) . . . . C6 C7 C8 N5 -179.8(2) . . . . C6 C7 C8 N6 -0.1(3) . . . . C7 C2 C3 C4 -0.7(4) . . . . _cod_database_fobs_code 4038995