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_7064128
_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
_atom_sites_solution_primary     iterative
_audit_creation_date             2025-07-05
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2018.12.18 svn.r3554 for Rigaku Oxford Diffraction, GUI svn.r1)
;
_audit_update_record
;
2025-07-29 deposited with the CCDC.	2025-11-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.119(5)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.760(3)
_cell_length_b                   10.7770(15)
_cell_length_c                   8.4910(11)
_cell_measurement_reflns_used    7604
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      23.41
_cell_measurement_theta_min      2.75
_cell_volume                     1864.0(4)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 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    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_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  0.0846
_diffrn_reflns_av_unetI/netI     0.0941
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            29713
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.436
_diffrn_reflns_theta_min         1.000
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.4973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1721 before and 0.0905 after correction. The Ratio of minimum to maximum transmission is 0.6672. 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    1.363
_exptl_crystal_description       irregular
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3828
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.1439
_refine_ls_R_factor_gt           0.0897
_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^)+(0.0557P)^2^+3.1658P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2320
_refine_ls_wR_factor_ref         0.2502
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2244
_reflns_number_total             3828
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5nj03844h3.cif
_cod_data_source_block           vsp-c6
_cod_database_code               7064128
_shelx_shelxl_version_number     2018/3
_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:
 C00N(H00C,H00N), C00R(H00A,H00B)
2.b Aromatic/amide H refined with riding coordinates:
 C00D(H00D), C00E(H00E), C00F(H00F), C00G(H00G), C00H(H00H), C00I(H00I),
 C00J(H00J), C00K(H00K), C00L(H00L), C00M(H00M), C00O(H00O), C00P(H00P),
 C00Q(H00Q), C00S(H00S)
;
_shelx_res_checksum              75628
_olex2_submission_special_instructions 'No special instructions were received'