Surprising Chemistry of 6.Azidotetrazolo[5,1.a]phthalazine: What a Purported Natural Product Reveals about the Polymorphism of Explosives
Numez Avila, Aaron Gabriel; Deschênes-Simard, Benoît; Arnold, Joseph E.; Morency, Mathieu; Chartrand, Daniel; Maris, Thierry; Berger, Gilles; Day, Graham M.; Hanessian, Stephen; Wuest, James D.; Journal of Organic Chemistry 87 (2022) 6680–6694; doi:10.1021/acs.joc.2c00369

data_4038995
_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
_cod_database_fobs_code 4038995