Polynitro-functionalized 4-phenyl-1<i>H</i>-pyrazoles as heat-resistant explosives.
Pandey, Krishna; Bhatia, Prachi; Mohammad, Khwaja; Ghule, Vikas D.; Kumar, Dheeraj; Organic & biomolecular chemistry 21 (2023) 6604–6616; doi:10.1039/d3ob00949a

data_7159487
_publ_section_title
;
 Polynitro-functionalized 4-phenyl-1<i>H</i>-pyrazoles as heat-resistant
 explosives.
;
_journal_issue                   32
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6604
_journal_page_last               6616
_journal_paper_doi               10.1039/d3ob00949a
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C10 H4 N7 O11, 2(H2 O), C3 H7 N8'
_chemical_formula_sum            'C13 H15 N15 O13'
_chemical_formula_weight         589.40
_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   mixed
_audit_creation_date             2023-06-15
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-06-15 deposited with the CCDC.	2023-07-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.1480(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.2504(7)
_cell_length_b                   22.4474(12)
_cell_length_c                   7.5543(4)
_cell_measurement_reflns_used    9808
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      26.925
_cell_measurement_theta_min      2.384
_cell_volume                     2234.0(2)
_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      150.00
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 QUEST Photon III C7'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0772
_diffrn_reflns_av_unetI/netI     0.0236
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            154320
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.258
_diffrn_reflns_theta_min         1.792
_exptl_absorpt_coefficient_mu    0.157
_exptl_absorpt_correction_T_max  0.7438
_exptl_absorpt_correction_T_min  0.7251
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1262 before and 0.0651 after correction.
The Ratio of minimum to maximum transmission is 0.9749.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'Clear Light Yellow'
_exptl_crystal_density_diffrn    1.752
_exptl_crystal_description       block
_exptl_crystal_F_000             1208
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Acetonitrile water'
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.526
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     383
_refine_ls_number_reflns         5004
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.0459
_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^)+(0.0461P)^2^+2.3042P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1099
_refine_ls_wR_factor_ref         0.1164
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4218
_reflns_number_total             5004
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00949a2.cif
_cod_data_source_block           dk_kp_hncptot_0016_0ma
_cod_depositor_comments
'Adding full bibliography for 7159486--7159487.cif.'
_cod_database_code               7159487
_shelx_shelxl_version_number     2019/3
_exptl_absorpt_special_details   block
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O13(H13C,H13D), O12(H12A)
2.b Rotating group:
 N15(H15A,H15B), N13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 N8(H8), C9(H9)
2.d X=CH2 refined with riding coordinates:
 N14(H14A,H14B)
2.e Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_shelx_res_checksum              99826
_olex2_submission_special_instructions 'No special instructions were received'