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#$Date: 2024-01-06 12:01:44 +0200 (Sat, 06 Jan 2024) $
#$Revision: 288913 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/00/1570010.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_1570010
loop_
_publ_author_name
'Dong, Yaqun'
'Li, Miao'
'Liu, Jing'
'Liu, Yuji'
'Huang, Wei'
'Shreeve, Jean'ne M.'
'Tang, Yongxing'
_publ_section_title
;
 Pushing the limits of the heat of detonation via the construction
 of polynitro bipyrazole.
;
_journal_issue                   12
_journal_name_full               'Materials horizons'
_journal_page_first              5729
_journal_page_last               5733
_journal_paper_doi               10.1039/d3mh01381b
_journal_volume                  10
_journal_year                    2023
_chemical_formula_sum            'C7 H3 N9 O10'
_chemical_formula_weight         373.18
_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-2014/7
_audit_update_record
;
2023-09-20 deposited with the CCDC.	2023-09-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.17
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.144
_cell_length_b                   12.629
_cell_length_c                   12.031
_cell_measurement_reflns_used    3098
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      49.04
_cell_measurement_theta_min      4.90
_cell_volume                     1371.579
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  ccd
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0
_diffrn_reflns_av_unetI/netI     0.0949
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_number            2381
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        66.869
_diffrn_reflns_theta_max         66.869
_diffrn_reflns_theta_min         5.112
_exptl_absorpt_coefficient_mu    1.525
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.807
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_transmission_factor_max   0.864
_exptl_transmission_factor_min   0.864
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         2381
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.123
_refine_ls_R_factor_all          0.1027
_refine_ls_R_factor_gt           0.0773
_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)+(0.0967P)²+0.9962P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2110
_refine_ls_wR_factor_ref         0.2290
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1587
_reflns_number_total             2381
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3mh01381b2.cif
_cod_data_source_block           1_a
_cod_depositor_comments
'Adding full bibliography for 1570008--1570010.cif.'
_cod_original_cell_volume        1371.7
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1570010
_shelx_shelxl_version_number     2014/7
_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.
;
_shelx_estimated_absorpt_t_min   0.838
_shelx_estimated_absorpt_t_max   0.888
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
C1 C 0.1512(5) 0.5263(4) 0.2098(4) 0.0728(12) Uani 1 1 d . . . . .
H1 H 0.0744 0.4863 0.1706 0.087 Uiso 1 1 calc R U . . .
C2 C 0.3017(5) 0.5035(3) 0.2131(3) 0.0630(10) Uani 1 1 d . . . . .
C3 C 0.3814(5) 0.5797(3) 0.2782(3) 0.0586(10) Uani 1 1 d . . . . .
C4 C 0.5377(4) 0.5972(3) 0.3183(3) 0.0571(10) Uani 1 1 d . . . . .
C5 C 0.6650(5) 0.5946(3) 0.2639(3) 0.0604(10) Uani 1 1 d . . . . .
C6 C 0.7840(5) 0.6140(3) 0.3433(4) 0.0680(11) Uani 1 1 d . . . . .
H6 H 0.8830 0.6173 0.3342 0.082 Uiso 1 1 calc R U . . .
C7 C 0.2940(5) 0.7275(3) 0.3882(4) 0.0648(11) Uani 1 1 d . . . . .
H7 H 0.3891 0.7624 0.3858 0.078 Uiso 1 1 calc R U . . .
N1 N 0.2750(4) 0.6448(3) 0.3099(3) 0.0620(9) Uani 1 1 d . . . . .
N2 N 0.1316(4) 0.6113(3) 0.2691(3) 0.0739(10) Uani 1 1 d . . . . .
N3 N 0.2893(5) 0.6888(3) 0.5070(3) 0.0785(11) Uani 1 1 d . . . . .
N4 N 0.1683(5) 0.8074(3) 0.3571(5) 0.0830(12) Uani 1 1 d . . . . .
N5 N 0.3583(5) 0.4097(3) 0.1707(3) 0.0695(10) Uani 1 1 d . . . . .
N6 N 0.5789(4) 0.6187(3) 0.4274(3) 0.0606(9) Uani 1 1 d . . . . .
N7 N 0.7270(4) 0.6275(3) 0.4383(3) 0.0626(9) Uani 1 1 d . . . . .
N8 N 0.8087(5) 0.6546(3) 0.5468(3) 0.0828(12) Uani 1 1 d . . . . .
N9 N 0.6687(5) 0.5807(3) 0.1461(3) 0.0725(10) Uani 1 1 d . . . . .
O1 O 0.3257(7) 0.7535(4) 0.5799(4) 0.1344(19) Uani 1 1 d . . . . .
O2 O 0.2551(5) 0.5988(3) 0.5198(3) 0.0929(11) Uani 1 1 d . . . . .
O3 O 0.0774(6) 0.8158(4) 0.4182(5) 0.150(2) Uani 1 1 d . . . . .
O4 O 0.1715(5) 0.8566(3) 0.2733(4) 0.1018(12) Uani 1 1 d . . . . .
O5 O 0.2710(5) 0.3492(3) 0.1179(3) 0.0887(11) Uani 1 1 d . . . . .
O6 O 0.4919(4) 0.3922(3) 0.1928(3) 0.0886(10) Uani 1 1 d . . . . .
O7 O 0.5540(5) 0.5855(3) 0.0813(3) 0.0990(12) Uani 1 1 d . . . . .
O8 O 0.7911(4) 0.5683(3) 0.1188(3) 0.1006(12) Uani 1 1 d . . . . .
O9 O 0.9407(5) 0.6519(5) 0.5515(4) 0.1269(17) Uani 1 1 d . . . . .
O10 O 0.7357(5) 0.6769(3) 0.6182(3) 0.0951(11) 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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 C1 C2 111.7(4) . . ?
N2 C1 H1 124.1 . . ?
C2 C1 H1 124.1 . . ?
C3 C2 C1 107.5(3) . . ?
C3 C2 N5 126.8(4) . . ?
C1 C2 N5 125.1(4) . . ?
N1 C3 C2 104.1(4) . . ?
N1 C3 C4 121.4(4) . . ?
C2 C3 C4 134.5(4) . . ?
N6 C4 C5 109.5(4) . . ?
N6 C4 C3 117.8(3) . . ?
C5 C4 C3 132.7(4) . . ?
C6 C5 C4 107.2(4) . . ?
C6 C5 N9 125.3(4) . . ?
C4 C5 N9 127.4(4) . . ?
N7 C6 C5 104.3(4) . . ?
N7 C6 H6 127.9 . . ?
C5 C6 H6 127.9 . . ?
N1 C7 N3 112.0(3) . . ?
N1 C7 N4 108.7(4) . . ?
N3 C7 N4 108.0(3) . . ?
N1 C7 H7 109.4 . . ?
N3 C7 H7 109.4 . . ?
N4 C7 H7 109.4 . . ?
C3 N1 N2 113.0(3) . . ?
C3 N1 C7 128.1(4) . . ?
N2 N1 C7 118.2(3) . . ?
C1 N2 N1 103.7(4) . . ?
O2 N3 O1 126.7(4) . . ?
O2 N3 C7 118.4(4) . . ?
O1 N3 C7 114.9(4) . . ?
O4 N4 O3 126.0(5) . . ?
O4 N4 C7 115.6(4) . . ?
O3 N4 C7 118.4(5) . . ?
O5 N5 O6 123.4(4) . . ?
O5 N5 C2 117.9(4) . . ?
O6 N5 C2 118.6(4) . . ?
C4 N6 N7 103.5(3) . . ?
C6 N7 N6 115.5(4) . . ?
C6 N7 N8 126.0(4) . . ?
N6 N7 N8 118.5(3) . . ?
O9 N8 O10 129.9(5) . . ?
O9 N8 N7 114.2(4) . . ?
O10 N8 N7 115.9(4) . . ?
O7 N9 O8 124.8(4) . . ?
O7 N9 C5 118.6(4) . . ?
O8 N9 C5 116.6(4) . . ?
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
C1 N2 1.318(6) . ?
C1 C2 1.401(6) . ?
C1 H1 0.9300 . ?
C2 C3 1.375(6) . ?
C2 N5 1.419(5) . ?
C3 N1 1.373(5) . ?
C3 C4 1.451(6) . ?
C4 N6 1.335(5) . ?
C4 C5 1.424(5) . ?
C5 C6 1.352(6) . ?
C5 N9 1.434(6) . ?
C6 N7 1.340(5) . ?
C6 H6 0.9300 . ?
C7 N1 1.398(5) . ?
C7 N3 1.517(6) . ?
C7 N4 1.531(6) . ?
C7 H7 0.9800 . ?
N1 N2 1.391(5) . ?
N3 O2 1.196(5) . ?
N3 O1 1.207(5) . ?
N4 O4 1.188(6) . ?
N4 O3 1.198(5) . ?
N5 O5 1.209(5) . ?
N5 O6 1.228(5) . ?
N6 N7 1.345(5) . ?
N7 N8 1.438(5) . ?
N8 O9 1.199(6) . ?
N8 O10 1.203(5) . ?
N9 O7 1.205(5) . ?
N9 O8 1.225(5) . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 C1 C2 C3 -0.3(5) . . . . ?
N2 C1 C2 N5 171.0(4) . . . . ?
C1 C2 C3 N1 -0.5(4) . . . . ?
N5 C2 C3 N1 -171.6(4) . . . . ?
C1 C2 C3 C4 176.0(4) . . . . ?
N5 C2 C3 C4 4.9(7) . . . . ?
N1 C3 C4 N6 44.7(5) . . . . ?
C2 C3 C4 N6 -131.4(5) . . . . ?
N1 C3 C4 C5 -136.5(4) . . . . ?
C2 C3 C4 C5 47.4(7) . . . . ?
N6 C4 C5 C6 0.7(5) . . . . ?
C3 C4 C5 C6 -178.2(4) . . . . ?
N6 C4 C5 N9 -175.8(4) . . . . ?
C3 C4 C5 N9 5.3(7) . . . . ?
C4 C5 C6 N7 -0.3(4) . . . . ?
N9 C5 C6 N7 176.3(4) . . . . ?
C2 C3 N1 N2 1.2(4) . . . . ?
C4 C3 N1 N2 -175.9(3) . . . . ?
C2 C3 N1 C7 171.2(4) . . . . ?
C4 C3 N1 C7 -5.9(6) . . . . ?
N3 C7 N1 C3 -87.3(5) . . . . ?
N4 C7 N1 C3 153.5(4) . . . . ?
N3 C7 N1 N2 82.3(5) . . . . ?
N4 C7 N1 N2 -37.0(5) . . . . ?
C2 C1 N2 N1 1.0(5) . . . . ?
C3 N1 N2 C1 -1.4(5) . . . . ?
C7 N1 N2 C1 -172.5(4) . . . . ?
N1 C7 N3 O2 -7.9(6) . . . . ?
N4 C7 N3 O2 111.7(5) . . . . ?
N1 C7 N3 O1 170.0(5) . . . . ?
N4 C7 N3 O1 -70.4(5) . . . . ?
N1 C7 N4 O4 -69.3(5) . . . . ?
N3 C7 N4 O4 169.0(4) . . . . ?
N1 C7 N4 O3 111.3(5) . . . . ?
N3 C7 N4 O3 -10.4(6) . . . . ?
C3 C2 N5 O5 177.3(4) . . . . ?
C1 C2 N5 O5 7.7(6) . . . . ?
C3 C2 N5 O6 -0.1(6) . . . . ?
C1 C2 N5 O6 -169.7(4) . . . . ?
C5 C4 N6 N7 -0.7(4) . . . . ?
C3 C4 N6 N7 178.4(3) . . . . ?
C5 C6 N7 N6 -0.1(5) . . . . ?
C5 C6 N7 N8 -177.3(4) . . . . ?
C4 N6 N7 C6 0.6(4) . . . . ?
C4 N6 N7 N8 177.9(3) . . . . ?
C6 N7 N8 O9 -9.1(7) . . . . ?
N6 N7 N8 O9 173.9(4) . . . . ?
C6 N7 N8 O10 170.5(4) . . . . ?
N6 N7 N8 O10 -6.5(6) . . . . ?
C6 C5 N9 O7 -165.0(4) . . . . ?
C4 C5 N9 O7 10.9(6) . . . . ?
C6 C5 N9 O8 12.6(6) . . . . ?
C4 C5 N9 O8 -171.5(4) . . . . ?
