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_7064126
_publ_section_title
;
 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 H9 N3 O2'
_chemical_formula_sum            'C9 H9 N3 O2'
_chemical_formula_weight         191.19
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2025-07-30 deposited with the CCDC.	2025-11-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.98(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.952(5)
_cell_length_b                   17.512(10)
_cell_length_c                   7.541(4)
_cell_measurement_reflns_used    424
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.69
_cell_measurement_theta_min      2.95
_cell_volume                     911.3(10)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.943
_diffrn_measured_fraction_theta_max 0.943
_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  0.7985
_diffrn_reflns_av_unetI/netI     0.7248
_diffrn_reflns_Laue_measured_fraction_full 0.943
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            6092
_diffrn_reflns_point_group_measured_fraction_full 0.943
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_theta_full        25.153
_diffrn_reflns_theta_max         25.153
_diffrn_reflns_theta_min         2.952
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_correction_T_min  0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_description       Neddle
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.090
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       0.03(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   0.892
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         1542
_refine_ls_number_restraints     491
_refine_ls_restrained_S_all      0.775
_refine_ls_R_factor_all          0.4566
_refine_ls_R_factor_gt           0.1849
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0947P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3717
_refine_ls_wR_factor_ref         0.5216
_reflns_Friedel_coverage         0.000
_reflns_number_gt                251
_reflns_number_total             1542
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5nj03844h3.cif
_cod_data_source_block           VSP-C5
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7064126
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.991
_shelx_estimated_absorpt_t_max   0.994
_shelx_res_checksum              98489