#------------------------------------------------------------------------------
#$Date: 2023-09-05 23:21:11 +0300 (Tue, 05 Sep 2023) $
#$Revision: 286180 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/94/7159486.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7159486
loop_
_publ_author_name
'Pandey, Krishna'
'Bhatia, Prachi'
'Mohammad, Khwaja'
'Ghule, Vikas D.'
'Kumar, Dheeraj'
_publ_section_title
;
 Polynitro-functionalized 4-phenyl-1H-pyrazoles as heat-resistant
 explosives.
;
_journal_issue                   32
_journal_name_full               'Organic & 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 H5 N7 O10'
_chemical_formula_sum            'C10 H5 N7 O10'
_chemical_formula_weight         383.21
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-06-09 deposited with the CCDC.	2023-07-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.903(15)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.911(2)
_cell_length_b                   20.066(7)
_cell_length_c                   11.124(4)
_cell_measurement_reflns_used    8317
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      0.972
_cell_measurement_theta_min      0.965
_cell_volume                     1476.0(9)
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      299(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0551
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            47494
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.311
_diffrn_reflns_theta_min         2.030
_exptl_absorpt_coefficient_mu    0.157
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.724
_exptl_crystal_description       needle
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   0.972
_exptl_transmission_factor_min   0.965
_refine_diff_density_max         0.419
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.923
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3658
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.923
_refine_ls_R_factor_all          0.0647
_refine_ls_R_factor_gt           0.0478
_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/[σ²(Fo²)+(0.1000P)²+0.5101P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1454
_refine_ls_wR_factor_ref         0.1557
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2778
_reflns_number_total             3669
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ob00949a2.cif
_cod_data_source_block           compd6
_cod_depositor_comments
'Adding full bibliography for 7159486--7159487.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7159486
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.3339(2) 0.54324(7) 0.24352(13) 0.0365(3) Uani 1 1 d . . . . .
N2 N 0.5124(2) 0.53592(7) 0.32926(14) 0.0384(3) Uani 1 1 d . . . . .
O2 O 0.8192(2) 0.54051(8) 0.53716(17) 0.0623(4) Uani 1 1 d . . . . .
O1 O 0.6709(2) 0.61554(10) 0.61694(16) 0.0656(5) Uani 1 1 d . . . . .
O10 O 0.0460(3) 0.83579(8) 0.41270(17) 0.0700(5) Uani 1 1 d . . . . .
N3 N 0.6758(2) 0.57711(8) 0.53382(16) 0.0416(4) Uani 1 1 d . . . . .
N7 N 0.0412(3) 0.81686(8) 0.51613(17) 0.0463(4) Uani 1 1 d . . . . .
O5 O 0.1689(3) 0.55924(9) 0.80851(16) 0.0715(5) Uani 1 1 d . . . . .
O9 O -0.0140(3) 0.85088(8) 0.58981(18) 0.0695(5) Uani 1 1 d . . . . .
N5 N 0.1146(3) 0.61653(9) 0.79481(15) 0.0475(4) Uani 1 1 d . . . . .
O6 O 0.0380(3) 0.64565(10) 0.86453(17) 0.0775(6) Uani 1 1 d . . . . .
N6 N -0.0050(3) 0.75624(9) 0.74602(17) 0.0527(4) Uani 1 1 d . . . . .
O7 O 0.1111(3) 0.78174(10) 0.83765(16) 0.0740(5) Uani 1 1 d . . . . .
O8 O -0.1885(3) 0.75859(10) 0.71659(19) 0.0764(6) Uani 1 1 d . . . . .
N4 N 0.0128(3) 0.60202(10) 0.21278(17) 0.0547(5) Uani 1 1 d . . . . .
C4 C 0.5004(2) 0.57327(8) 0.42534(16) 0.0332(3) Uani 1 1 d . . . . .
C5 C 0.2401(2) 0.64625(8) 0.49518(15) 0.0322(3) Uani 1 1 d . . . . .
C3 C 0.3146(2) 0.60555(8) 0.40653(15) 0.0330(3) Uani 1 1 d . . . . .
C6 C 0.2196(3) 0.61639(8) 0.60346(15) 0.0343(3) Uani 1 1 d . . . . .
H6 H 0.258387 0.572256 0.621402 0.041 Uiso 1 1 calc R U . . .
C10 C 0.1833(3) 0.71213(9) 0.46968(16) 0.0357(4) Uani 1 1 d . . . . .
H10 H 0.197694 0.732490 0.397660 0.043 Uiso 1 1 calc R U . . .
O3 O -0.0515(3) 0.58238(13) 0.10769(18) 0.0917(7) Uani 1 1 d . . . . .
C8 C 0.0830(3) 0.71890(9) 0.66031(16) 0.0369(4) Uani 1 1 d . . . . .
C2 C 0.2138(3) 0.58462(9) 0.28692(16) 0.0368(4) Uani 1 1 d . . . . .
C9 C 0.1052(3) 0.74763(8) 0.55162(16) 0.0359(4) Uani 1 1 d . . . . .
C7 C 0.1412(3) 0.65248(9) 0.68465(15) 0.0359(4) Uani 1 1 d . . . . .
C1 C 0.2955(4) 0.50524(10) 0.12565(19) 0.0526(5) Uani 1 1 d . . . . .
H1A H 0.413063 0.479426 0.126961 0.079 Uiso 1 1 calc R U . . .
H1B H 0.266074 0.535524 0.055850 0.079 Uiso 1 1 calc R U . . .
H1C H 0.182427 0.476009 0.117309 0.079 Uiso 1 1 calc R U . . .
O4 O -0.0840(4) 0.63596(19) 0.2624(3) 0.1603(17) Uani 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N1 C2 110.36(14) . . ?
N2 N1 C1 118.08(15) . . ?
C2 N1 C1 131.49(17) . . ?
C4 N2 N1 104.66(14) . . ?
O1 N3 O2 124.08(17) . . ?
O1 N3 C4 117.95(16) . . ?
O2 N3 C4 117.96(16) . . ?
O9 N7 O10 124.25(18) . . ?
O9 N7 C9 118.58(17) . . ?
O10 N7 C9 117.17(16) . . ?
O5 N5 O6 123.95(18) . . ?
O5 N5 C7 117.43(16) . . ?
O6 N5 C7 118.62(18) . . ?
O7 N6 O8 126.44(19) . . ?
O7 N6 C8 117.46(18) . . ?
O8 N6 C8 116.09(18) . . ?
O3 N4 O4 122.8(2) . . ?
O3 N4 C2 120.39(19) . . ?
O4 N4 C2 116.78(18) . . ?
N2 C4 C3 114.24(15) . . ?
N2 C4 N3 118.01(15) . . ?
C3 C4 N3 127.74(15) . . ?
C10 C5 C6 119.69(15) . . ?
C10 C5 C3 121.47(14) . . ?
C6 C5 C3 118.79(15) . . ?
C2 C3 C4 100.83(14) . . ?
C2 C3 C5 129.42(15) . . ?
C4 C3 C5 129.55(15) . . ?
C7 C6 C5 119.85(16) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C9 C10 C5 119.87(15) . . ?
C9 C10 H10 120.1 . . ?
C5 C10 H10 120.1 . . ?
C9 C8 C7 117.87(15) . . ?
C9 C8 N6 121.50(17) . . ?
C7 C8 N6 120.60(16) . . ?
N1 C2 C3 109.90(15) . . ?
N1 C2 N4 122.22(16) . . ?
C3 C2 N4 127.88(16) . . ?
C10 C9 C8 121.52(16) . . ?
C10 C9 N7 116.87(16) . . ?
C8 C9 N7 121.59(15) . . ?
C6 C7 C8 121.20(15) . . ?
C6 C7 N5 116.86(16) . . ?
C8 C7 N5 121.89(15) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 N2 1.330(2) . ?
N1 C2 1.358(2) . ?
N1 C1 1.473(2) . ?
N2 C4 1.327(2) . ?
O2 N3 1.225(2) . ?
O1 N3 1.212(2) . ?
O10 N7 1.221(2) . ?
N3 C4 1.443(2) . ?
N7 O9 1.210(2) . ?
N7 C9 1.476(2) . ?
O5 N5 1.205(3) . ?
N5 O6 1.209(2) . ?
N5 C7 1.479(2) . ?
N6 O7 1.212(2) . ?
N6 O8 1.215(3) . ?
N6 C8 1.476(2) . ?
N4 O3 1.190(3) . ?
N4 O4 1.196(3) . ?
N4 C2 1.437(2) . ?
C4 C3 1.399(2) . ?
C5 C10 1.385(2) . ?
C5 C6 1.389(2) . ?
C5 C3 1.483(2) . ?
C3 C2 1.376(2) . ?
C6 C7 1.385(2) . ?
C6 H6 0.9300 . ?
C10 C9 1.384(2) . ?
C10 H10 0.9300 . ?
C8 C9 1.387(3) . ?
C8 C7 1.396(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
