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#$Date: 2022-05-22 15:31:21 +0300 (Sun, 22 May 2022) $
#$Revision: 275607 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/89/4038993.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_4038993
loop_
_publ_author_name
'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.'
_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      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             2021-02-02
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_cell_angle_alpha                90
_cell_angle_beta                 92.319(1)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.9733(1)
_cell_length_b                   12.1827(3)
_cell_length_c                   14.5857(3)
_cell_measurement_reflns_used    5167
_cell_measurement_temperature    100
_cell_measurement_theta_max      71.704
_cell_measurement_theta_min      3.032
_cell_volume                     883.00(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 APEX2 CCD'
_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 APEX'
_diffrn_measurement_method       'ω 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  0.0415
_diffrn_reflns_av_unetI/netI     0.0163
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_number            3442
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         71.920
_diffrn_reflns_theta_min         3.032
_diffrn_source                   'Microfocus Source'
_diffrn_source_current           0.65
_diffrn_source_power             0.02912
_diffrn_source_target            Cu
_diffrn_source_type              'Incoatec I\mS High Brilliance Microsource'
_diffrn_source_voltage           70
_exptl_absorpt_coefficient_mu    0.954
_exptl_absorpt_correction_T_max  0.7535
_exptl_absorpt_correction_T_min  0.6198
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.

Final HKLF 4 output contains 67246 reflections, Rint = 0.0415
 (60184 with I > 3sig(I), Rint = 0.0412)
;
_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    1.596
_exptl_crystal_description       Block
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Flack x determined using 1620 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         3442
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0351
_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/[σ²(Fo²)+(0.0846P)²+0.0881P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1015
_refine_ls_wR_factor_ref         0.1015
_reflns_Friedel_coverage         0.902
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                3437
_reflns_number_total             3442
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jw22776.cif
_cod_data_source_block           jw22776
_cod_database_code               4038993
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
N1A N 0.5978(4) 0.70758(17) 0.51780(14) 0.0284(4) Uani 1 1 d . . . . .
N2A N 0.8066(4) 0.63573(17) 0.52934(13) 0.0303(4) Uani 1 1 d . . . . .
N3A N 0.8805(4) 0.59599(17) 0.45149(13) 0.0285(4) Uani 1 1 d . . . . .
N4A N 0.7165(4) 0.64316(16) 0.38716(13) 0.0246(4) Uani 1 1 d . . . . .
N5A N 0.7323(4) 0.61886(15) 0.29622(13) 0.0258(4) Uani 1 1 d . . . . .
N6A N 0.5478(4) 0.65549(17) 0.15007(14) 0.0279(4) Uani 1 1 d . . . . .
N7A N 0.7392(4) 0.59919(17) 0.12166(13) 0.0263(4) Uani 1 1 d . . . . .
N8A N 0.8964(4) 0.55247(18) 0.08545(15) 0.0327(5) Uani 1 1 d . . . . .
C1A C 0.5441(5) 0.71129(19) 0.42847(15) 0.0245(4) Uani 1 1 d . . . . .
C2A C 0.3531(4) 0.77155(19) 0.37138(16) 0.0245(4) Uani 1 1 d . . . . .
C3A C 0.1740(5) 0.8490(2) 0.40556(16) 0.0269(5) Uani 1 1 d . . . . .
H3A H 0.170968 0.863113 0.468168 0.032 Uiso 1 1 calc R U . . .
C4A C 0.0016(5) 0.9041(2) 0.34424(17) 0.0291(5) Uani 1 1 d . . . . .
H4A H -0.118821 0.955273 0.366086 0.035 Uiso 1 1 calc R U . . .
C5A C 0.0065(5) 0.8836(2) 0.24992(18) 0.0285(5) Uani 1 1 d . . . . .
H5A H -0.111039 0.921165 0.209865 0.034 Uiso 1 1 calc R U . . .
C6A C 0.1845(5) 0.80809(19) 0.21555(16) 0.0269(5) Uani 1 1 d . . . . .
H6A H 0.187670 0.795078 0.152773 0.032 Uiso 1 1 calc R U . . .
C7A C 0.3600(4) 0.75142(18) 0.27664(15) 0.0240(4) Uani 1 1 d . . . . .
C8A C 0.5553(4) 0.67205(17) 0.24485(16) 0.0242(5) Uani 1 1 d . . . . .
N1B N 1.1228(4) 0.29234(17) -0.00834(13) 0.0281(4) Uani 1 1 d . . . . .
N2B N 1.3296(4) 0.36549(17) -0.01248(14) 0.0301(4) Uani 1 1 d . . . . .
N3B N 1.3940(4) 0.40746(17) 0.06754(14) 0.0284(4) Uani 1 1 d . . . . .
N4B N 1.2256(4) 0.36016(16) 0.12602(13) 0.0250(4) Uani 1 1 d . . . . .
N5B N 1.2282(4) 0.38769(16) 0.21657(13) 0.0257(4) Uani 1 1 d . . . . .
N6B N 1.0279(4) 0.35588(17) 0.35524(13) 0.0271(4) Uani 1 1 d . . . . .
N7B N 1.2200(4) 0.41105(17) 0.38953(13) 0.0268(4) Uani 1 1 d . . . . .
N8B N 1.3778(4) 0.45750(18) 0.43055(15) 0.0320(5) Uani 1 1 d . . . . .
C1B C 1.0603(4) 0.28979(19) 0.07906(15) 0.0248(4) Uani 1 1 d . . . . .
C2B C 0.8664(4) 0.22962(19) 0.12946(16) 0.0247(5) Uani 1 1 d . . . . .
C3B C 0.6942(4) 0.1501(2) 0.08968(15) 0.0267(5) Uani 1 1 d . . . . .
H3B H 0.698854 0.134320 0.027380 0.032 Uiso 1 1 calc R U . . .
C4B C 0.5174(5) 0.0956(2) 0.14454(16) 0.0281(5) Uani 1 1 d . . . . .
H4B H 0.401722 0.043016 0.118808 0.034 Uiso 1 1 calc R U . . .
C5B C 0.5105(4) 0.11885(19) 0.23867(17) 0.0274(5) Uani 1 1 d . . . . .
H5B H 0.390886 0.081330 0.274737 0.033 Uiso 1 1 calc R U . . .
C6B C 0.6801(5) 0.1971(2) 0.27825(16) 0.0262(5) Uani 1 1 d . . . . .
H6B H 0.674175 0.212358 0.340600 0.031 Uiso 1 1 calc R U . . .
C7B C 0.8612(4) 0.25318(18) 0.22379(15) 0.0243(5) Uani 1 1 d . . . . .
C8B C 1.0479(4) 0.33528(18) 0.26166(16) 0.0244(5) Uani 1 1 d . . . . .
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
C1A N1A N2A 105.45(19) . .
N3A N2A N1A 111.82(19) . .
N2A N3A N4A 105.35(19) . .
N3A N4A N5A 121.83(18) . .
N3A N4A C1A 109.18(18) . .
C1A N4A N5A 128.98(18) . .
C8A N5A N4A 112.72(18) . .
N7A N6A C8A 114.52(19) . .
N8A N7A N6A 171.0(2) . .
N1A C1A N4A 108.2(2) . .
N1A C1A C2A 133.7(2) . .
N4A C1A C2A 118.09(19) . .
C3A C2A C1A 123.5(2) . .
C3A C2A C7A 120.5(2) . .
C7A C2A C1A 116.0(2) . .
C2A C3A H3A 120.6 . .
C4A C3A C2A 118.8(2) . .
C4A C3A H3A 120.6 . .
C3A C4A H4A 119.6 . .
C3A C4A C5A 120.9(2) . .
C5A C4A H4A 119.6 . .
C4A C5A H5A 119.6 . .
C6A C5A C4A 120.7(2) . .
C6A C5A H5A 119.6 . .
C5A C6A H6A 120.4 . .
C5A C6A C7A 119.2(2) . .
C7A C6A H6A 120.4 . .
C2A C7A C8A 118.1(2) . .
C6A C7A C2A 119.9(2) . .
C6A C7A C8A 121.9(2) . .
N5A C8A N6A 119.2(2) . .
N5A C8A C7A 126.1(2) . .
N6A C8A C7A 114.76(19) . .
C1B N1B N2B 105.35(19) . .
N3B N2B N1B 112.04(19) . .
N2B N3B N4B 105.24(19) . .
N3B N4B N5B 121.75(19) . .
N3B N4B C1B 109.29(18) . .
C1B N4B N5B 128.90(19) . .
C8B N5B N4B 112.92(19) . .
N7B N6B C8B 113.77(19) . .
N8B N7B N6B 171.2(2) . .
N1B C1B N4B 108.09(19) . .
N1B C1B C2B 133.8(2) . .
N4B C1B C2B 118.06(19) . .
C3B C2B C1B 123.5(2) . .
C3B C2B C7B 120.7(2) . .
C7B C2B C1B 115.8(2) . .
C2B C3B H3B 120.5 . .
C4B C3B C2B 119.0(2) . .
C4B C3B H3B 120.5 . .
C3B C4B H4B 119.6 . .
C3B C4B C5B 120.7(2) . .
C5B C4B H4B 119.6 . .
C4B C5B H5B 119.7 . .
C6B C5B C4B 120.6(2) . .
C6B C5B H5B 119.7 . .
C5B C6B H6B 120.2 . .
C5B C6B C7B 119.6(2) . .
C7B C6B H6B 120.2 . .
C2B C7B C8B 118.3(2) . .
C6B C7B C2B 119.5(2) . .
C6B C7B C8B 122.2(2) . .
N5B C8B N6B 118.9(2) . .
N5B C8B C7B 125.9(2) . .
N6B C8B C7B 115.1(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1A N2A 1.363(3) .
N1A C1A 1.320(3) .
N2A N3A 1.301(3) .
N3A N4A 1.347(3) .
N4A N5A 1.364(3) .
N4A C1A 1.352(3) .
N5A C8A 1.305(3) .
N6A N7A 1.257(3) .
N6A C8A 1.396(3) .
N7A N8A 1.117(3) .
C1A C2A 1.439(3) .
C2A C3A 1.403(3) .
C2A C7A 1.405(3) .
C3A H3A 0.9300 .
C3A C4A 1.387(3) .
C4A H4A 0.9300 .
C4A C5A 1.399(4) .
C5A H5A 0.9300 .
C5A C6A 1.385(3) .
C6A H6A 0.9300 .
C6A C7A 1.403(3) .
C7A C8A 1.459(3) .
N1B N2B 1.364(3) .
N1B C1B 1.325(3) .
N2B N3B 1.302(3) .
N3B N4B 1.349(3) .
N4B N5B 1.362(3) .
N4B C1B 1.355(3) .
N5B C8B 1.301(3) .
N6B N7B 1.255(3) .
N6B C8B 1.395(3) .
N7B N8B 1.121(3) .
C1B C2B 1.437(3) .
C2B C3B 1.403(3) .
C2B C7B 1.407(3) .
C3B H3B 0.9300 .
C3B C4B 1.383(3) .
C4B H4B 0.9300 .
C4B C5B 1.403(3) .
C5B H5B 0.9300 .
C5B C6B 1.383(3) .
C6B H6B 0.9300 .
C6B C7B 1.402(3) .
C7B C8B 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
N1A N2A N3A N4A 0.2(3) . . . .
N1A C1A C2A C3A 2.2(4) . . . .
N1A C1A C2A C7A -179.8(2) . . . .
N2A N1A C1A N4A 0.0(2) . . . .
N2A N1A C1A C2A -178.7(2) . . . .
N2A N3A N4A N5A -178.67(19) . . . .
N2A N3A N4A C1A -0.1(3) . . . .
N3A N4A N5A C8A 179.4(2) . . . .
N3A N4A C1A N1A 0.0(3) . . . .
N3A N4A C1A C2A 179.04(18) . . . .
N4A N5A C8A N6A 179.95(18) . . . .
N4A N5A C8A C7A 1.2(3) . . . .
N4A C1A C2A C3A -176.4(2) . . . .
N4A C1A C2A C7A 1.5(3) . . . .
N5A N4A C1A N1A 178.5(2) . . . .
N5A N4A C1A C2A -2.5(3) . . . .
N7A N6A C8A N5A -8.4(3) . . . .
N7A N6A C8A C7A 170.58(19) . . . .
C1A N1A N2A N3A -0.1(3) . . . .
C1A N4A N5A C8A 1.2(3) . . . .
C1A C2A C3A C4A 178.8(2) . . . .
C1A C2A C7A C6A -178.78(19) . . . .
C1A C2A C7A C8A 0.4(3) . . . .
C2A C3A C4A C5A -0.4(3) . . . .
C2A C7A C8A N5A -1.9(3) . . . .
C2A C7A C8A N6A 179.25(19) . . . .
C3A C2A C7A C6A -0.8(3) . . . .
C3A C2A C7A C8A 178.4(2) . . . .
C3A C4A C5A C6A -0.2(4) . . . .
C4A C5A C6A C7A 0.4(3) . . . .
C5A C6A C7A C2A 0.1(3) . . . .
C5A C6A C7A C8A -179.0(2) . . . .
C6A C7A C8A N5A 177.3(2) . . . .
C6A C7A C8A N6A -1.6(3) . . . .
C7A C2A C3A C4A 0.9(3) . . . .
N1B N2B N3B N4B 0.3(2) . . . .
N1B C1B C2B C3B 2.6(4) . . . .
N1B C1B C2B C7B -178.7(2) . . . .
N2B N1B C1B N4B 0.2(2) . . . .
N2B N1B C1B C2B -178.9(2) . . . .
N2B N3B N4B N5B -177.6(2) . . . .
N2B N3B N4B C1B -0.2(2) . . . .
N3B N4B N5B C8B 178.58(19) . . . .
N3B N4B C1B N1B 0.0(2) . . . .
N3B N4B C1B C2B 179.26(18) . . . .
N4B N5B C8B N6B -179.84(19) . . . .
N4B N5B C8B C7B 1.3(3) . . . .
N4B C1B C2B C3B -176.4(2) . . . .
N4B C1B C2B C7B 2.2(3) . . . .
N5B N4B C1B N1B 177.2(2) . . . .
N5B N4B C1B C2B -3.6(3) . . . .
N7B N6B C8B N5B -11.2(3) . . . .
N7B N6B C8B C7B 167.76(19) . . . .
C1B N1B N2B N3B -0.3(2) . . . .
C1B N4B N5B C8B 1.7(3) . . . .
C1B C2B C3B C4B 179.0(2) . . . .
C1B C2B C7B C6B -179.2(2) . . . .
C1B C2B C7B C8B 0.3(3) . . . .
C2B C3B C4B C5B -0.3(3) . . . .
C2B C7B C8B N5B -2.3(3) . . . .
C2B C7B C8B N6B 178.86(19) . . . .
C3B C2B C7B C6B -0.5(3) . . . .
C3B C2B C7B C8B 179.0(2) . . . .
C3B C4B C5B C6B 0.2(4) . . . .
C4B C5B C6B C7B -0.3(3) . . . .
C5B C6B C7B C2B 0.4(3) . . . .
C5B C6B C7B C8B -179.1(2) . . . .
C6B C7B C8B N5B 177.2(2) . . . .
C6B C7B C8B N6B -1.6(3) . . . .
C7B C2B C3B C4B 0.5(3) . . . .

_cod_database_fobs_code 4038993
