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_7064124
_publ_section_title
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 Single-step nitration of N,N&#x2032;-Bispyrrolylmethane: Polynitro
 Derivatives as Insensitive Energetic Materials
;
_journal_name_full               'New Journal of Chemistry'
_journal_paper_doi               10.1039/D5NJ03844H
_journal_year                    2025
_chemical_formula_moiety         'C9 H8 N4 O4'
_chemical_formula_sum            'C9 H8 N4 O4'
_chemical_formula_weight         236.19
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2025-07-25
_audit_creation_method
;
Olex2 1.5
(compiled 2025.04.05 svn.rf049d14d for OlexSys, GUI svn.r7217)
;
_audit_update_record
;
2025-07-29 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                   10.2722(5)
_cell_length_b                   8.8323(4)
_cell_length_c                   11.4857(5)
_cell_measurement_reflns_used    7933
_cell_measurement_temperature    298
_cell_measurement_theta_max      25.67
_cell_measurement_theta_min      2.31
_cell_volume                     1042.06(8)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      298
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0364
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8480
_diffrn_reflns_point_group_measured_fraction_full 0.912
_diffrn_reflns_point_group_measured_fraction_max 0.904
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.686
_diffrn_reflns_theta_min         2.306
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6340
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1492 before and 0.0645 after correction.
The Ratio of minimum to maximum transmission is 0.8507.
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    1.506
_exptl_crystal_description       irregular
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.443
_refine_diff_density_min         -0.452
_refine_diff_density_rms         0.124
_refine_ls_abs_structure_details
;
 Flack x determined using 685 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.6(4)
_refine_ls_extinction_coef       0.105(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.256
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         1799
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.255
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0498
_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^)+(0.0645P)^2^+0.0498P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1041
_refine_ls_wR_factor_ref         0.1053
_reflns_Friedel_coverage         0.715
_reflns_Friedel_fraction_full    0.815
_reflns_Friedel_fraction_max     0.799
_reflns_number_gt                1712
_reflns_number_total             1799
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5nj03844h3.cif
_cod_data_source_block           VSP-C9
_cod_database_code               7064124
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.988
_shelx_estimated_absorpt_t_min   0.976
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00B(H00A,H00B)
2.b Aromatic/amide H refined with riding coordinates:
 C008(H008), C00C(H00C), C00E(H00E), C00F(H00F), C00G(H00G), C00H(H00H)
;
_shelx_res_checksum              95228
_olex2_submission_special_instructions 'No special instructions were received'