Single-step nitration of N,N′-Bispyrrolylmethane: Polynitro Derivatives as Insensitive Energetic Materials
Panda, Pradeepta; Shanmugapriya, V.; New Journal of Chemistry  (2025) –; doi:10.1039/D5NJ03844H

data_7064125
_publ_section_title
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 Single-step nitration of N,N&#x2032;-Bispyrrolylmethane: Polynitro
 Derivatives as Insensitive Energetic Materials
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_journal_name_full               'New Journal of Chemistry'
_journal_paper_doi               10.1039/D5NJ03844H
_journal_year                    2025
_chemical_formula_moiety         'C9 H6 N6 O8'
_chemical_formula_sum            'C9 H6 N6 O8'
_chemical_formula_weight         326.20
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2025-04-17
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2018.12.18 svn.r3554 for Rigaku Oxford Diffraction, GUI svn.r1)
;
_audit_update_record
;
2025-07-30 deposited with the CCDC.	2025-11-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.5849(17)
_cell_length_b                   10.4912(8)
_cell_length_c                   6.2223(4)
_cell_measurement_reflns_used    2890
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.87
_cell_measurement_theta_min      2.93
_cell_volume                     1213.21(16)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0725
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            13416
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.021
_diffrn_reflns_theta_max         25.021
_diffrn_reflns_theta_min         2.229
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.160
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6712
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1015 before and 0.0579 after correction.
The Ratio of minimum to maximum transmission is 0.9001.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.786
_exptl_crystal_description       needle
_exptl_crystal_F_000             664
_refine_diff_density_max         0.137
_refine_diff_density_min         -0.132
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details
;
 Refined as a perfect inversion twin.
;
_refine_ls_abs_structure_Flack   0.5
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2037
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0306
_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^)+(0.0279P)^2^+0.2441P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0687
_refine_ls_wR_factor_ref         0.0721
_reflns_Friedel_coverage         0.818
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                1848
_reflns_number_total             2037
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5nj03844h3.cif
_cod_data_source_block           VSP-c2
_cod_database_code               7064125
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H2(0.055) H3(0.055) H5A(0.045) H5B(0.045) H6(0.044) H8(0.045)
 Fixed X: H2(0.972021) H3(0.972877) H5A(0.773651) H5B(0.776297) H6(0.727381)
 H8(0.54104)
 Fixed Y: H2(0.448931) H3(0.319955) H5A(0.118184) H5B(0.194509) H6(0.354593)
 H8(0.338222)
 Fixed Z: H2(0.397659) H3(0.735563) H5A(0.43433) H5B(0.217454) H6(0.712376)
 H8(0.383841)
;
_shelx_res_checksum              15217