#------------------------------------------------------------------------------
#$Date: 2024-01-06 12:01:44 +0200 (Sat, 06 Jan 2024) $
#$Revision: 288913 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/00/1570009.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_1570009
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_moiety         'C8 H4 N6 O4'
_chemical_formula_sum            'C8 H4 N6 O4'
_chemical_formula_weight         248.17
_chemical_name_systematic        123
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2023-03-10
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-09-19 deposited with the CCDC.	2023-09-27 downloaded from the CCDC.
;
_cell_angle_alpha                79.354(3)
_cell_angle_beta                 78.910(3)
_cell_angle_gamma                72.855(3)
_cell_formula_units_Z            2
_cell_length_a                   5.0954(2)
_cell_length_b                   8.4208(4)
_cell_length_c                   11.6907(5)
_cell_measurement_reflns_used    3017
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      68.23
_cell_measurement_theta_min      3.89
_cell_volume                     465.97(4)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       'Bruker APEX2'
_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 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      193.00
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0454
_diffrn_reflns_av_unetI/netI     0.0411
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6641
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.223
_diffrn_reflns_theta_min         3.889
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.277
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5687
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1090 before and 0.0600 after correction.
The Ratio of minimum to maximum transmission is 0.7551.
The λ/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    1.769
_exptl_crystal_description       block
_exptl_crystal_F_000             252
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.393
_refine_diff_density_rms         0.087
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         1689
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0664
_refine_ls_R_factor_gt           0.0598
_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)+(0.0853P)²+1.3876P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1939
_refine_ls_wR_factor_ref         0.1983
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1447
_reflns_number_total             1689
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3mh01381b2.cif
_cod_data_source_block           cu_20230309_zm_nlg_dyq_4_0m
_cod_depositor_comments
'Adding full bibliography for 1570008--1570010.cif.'
_cod_database_code               1570009
_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.
;
_shelx_estimated_absorpt_t_max   0.872
_shelx_estimated_absorpt_t_min   0.852
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 N6_$1-O1
 2.9 with sigma of 0.002
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C5(H5), C8(H8)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
O1 O 1.1104(6) 0.9958(4) 0.1119(2) 0.0374(7) Uani 1 1 d D . . . .
C1 C 1.2051(8) 0.6575(5) 0.0788(3) 0.0297(8) Uani 1 1 d . . . . .
H1 H 1.345195 0.700062 0.027705 0.036 Uiso 1 1 calc R U . . .
N1 N 1.1995(7) 0.4988(4) 0.0951(3) 0.0321(8) Uani 1 1 d . . . . .
C2 C 0.9789(8) 0.7548(5) 0.1463(3) 0.0255(8) Uani 1 1 d . . . . .
N2 N 0.9691(7) 0.4937(4) 0.1751(3) 0.0273(7) Uani 1 1 d . . . . .
O2 O 0.6691(6) 1.0131(3) 0.1523(3) 0.0381(7) Uani 1 1 d . . . . .
C3 C 0.8254(7) 0.6473(4) 0.2097(3) 0.0236(8) Uani 1 1 d . . . . .
N3 N 0.5029(7) 0.5057(4) 0.3279(3) 0.0273(7) Uani 1 1 d . . . . .
O3 O 0.6193(6) 0.9514(4) 0.3806(3) 0.0350(7) Uani 1 1 d . . . . .
C4 C 0.8852(9) 0.3480(5) 0.2129(3) 0.0320(9) Uani 1 1 d . . . . .
H4 H 0.993227 0.245193 0.186183 0.038 Uiso 1 1 calc R U . . .
O4 O 0.1730(6) 1.0384(3) 0.3849(2) 0.0355(7) Uani 1 1 d . . . . .
N4 N 0.2649(7) 0.5216(4) 0.4064(3) 0.0305(7) Uani 1 1 d . . . . .
C5 C 0.6486(9) 0.3549(5) 0.2880(3) 0.0307(9) Uani 1 1 d . . . . .
H5 H 0.582369 0.257961 0.313315 0.037 Uiso 1 1 calc R U . . .
N5 N 0.3941(6) 0.9297(4) 0.3761(2) 0.0248(7) Uani 1 1 d . . . . .
N6 N 0.9130(7) 0.9325(4) 0.1383(2) 0.0274(7) Uani 1 1 d . . . . .
C6 C 0.5864(8) 0.6511(4) 0.2975(3) 0.0232(8) Uani 1 1 d . . . . .
C7 C 0.3897(7) 0.7640(4) 0.3633(3) 0.0238(8) Uani 1 1 d . . . . .
C8 C 0.1974(8) 0.6805(5) 0.4275(3) 0.0280(8) Uani 1 1 d . . . . .
H8 H 0.038931 0.730074 0.479528 0.034 Uiso 1 1 calc R U . . .
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
N1 C1 H1 124.3 . . ?
N1 C1 C2 111.5(3) . . ?
C2 C1 H1 124.3 . . ?
C1 N1 N2 104.5(3) . . ?
C1 C2 N6 124.4(3) . . ?
C3 C2 C1 106.8(3) . . ?
C3 C2 N6 128.5(3) . . ?
N1 N2 C3 113.3(3) . . ?
N1 N2 C4 122.3(3) . . ?
C3 N2 C4 124.3(3) . . ?
C2 C3 C6 139.4(3) . . ?
N2 C3 C2 103.8(3) . . ?
N2 C3 C6 116.7(3) . . ?
N4 N3 C5 122.2(3) . . ?
N4 N3 C6 113.3(3) . . ?
C6 N3 C5 124.4(3) . . ?
N2 C4 H4 120.7 . . ?
C5 C4 N2 118.7(3) . . ?
C5 C4 H4 120.7 . . ?
C8 N4 N3 104.2(3) . . ?
N3 C5 H5 120.6 . . ?
C4 C5 N3 118.7(3) . . ?
C4 C5 H5 120.6 . . ?
O3 N5 C7 117.5(3) . . ?
O4 N5 O3 124.4(3) . . ?
O4 N5 C7 118.1(3) . . ?
O1 N6 C2 116.6(3) . . ?
O2 N6 O1 124.2(3) . . ?
O2 N6 C2 119.1(3) . . ?
N3 C6 C3 116.6(3) . . ?
N3 C6 C7 104.2(3) . . ?
C7 C6 C3 139.2(3) . . ?
C6 C7 N5 127.6(3) . . ?
C6 C7 C8 107.1(3) . . ?
C8 C7 N5 125.0(3) . . ?
N4 C8 C7 111.3(3) . . ?
N4 C8 H8 124.4 . . ?
C7 C8 H8 124.4 . . ?
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
O1 N6 1.235(4) . ?
C1 H1 0.9500 . ?
C1 N1 1.323(5) . ?
C1 C2 1.397(5) . ?
N1 N2 1.359(4) . ?
C2 C3 1.388(5) . ?
C2 N6 1.424(5) . ?
N2 C3 1.376(4) . ?
N2 C4 1.386(5) . ?
O2 N6 1.224(4) . ?
C3 C6 1.430(5) . ?
N3 N4 1.361(4) . ?
N3 C5 1.382(5) . ?
N3 C6 1.376(5) . ?
O3 N5 1.226(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.341(6) . ?
O4 N5 1.224(4) . ?
N4 C8 1.337(5) . ?
C5 H5 0.9500 . ?
N5 C7 1.438(5) . ?
C6 C7 1.383(5) . ?
C7 C8 1.395(5) . ?
C8 H8 0.9500 . ?
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
C1 N1 N2 C3 0.5(4) . . . . ?
C1 N1 N2 C4 177.9(3) . . . . ?
C1 C2 C3 N2 -0.4(4) . . . . ?
C1 C2 C3 C6 176.1(4) . . . . ?
C1 C2 N6 O1 -31.3(5) . . . . ?
C1 C2 N6 O2 145.4(4) . . . . ?
N1 C1 C2 C3 0.8(4) . . . . ?
N1 C1 C2 N6 -173.2(3) . . . . ?
N1 N2 C3 C2 0.0(4) . . . . ?
N1 N2 C3 C6 -177.5(3) . . . . ?
N1 N2 C4 C5 -177.0(4) . . . . ?
C2 C1 N1 N2 -0.8(4) . . . . ?
C2 C3 C6 N3 175.7(4) . . . . ?
C2 C3 C6 C7 -0.3(8) . . . . ?
N2 C3 C6 N3 -8.1(5) . . . . ?
N2 C3 C6 C7 175.9(4) . . . . ?
N2 C4 C5 N3 -2.2(6) . . . . ?
C3 C2 N6 O1 156.0(4) . . . . ?
C3 C2 N6 O2 -27.3(5) . . . . ?
C3 N2 C4 C5 0.1(6) . . . . ?
C3 C6 C7 N5 -11.6(7) . . . . ?
C3 C6 C7 C8 175.3(4) . . . . ?
N3 N4 C8 C7 0.0(4) . . . . ?
N3 C6 C7 N5 172.1(3) . . . . ?
N3 C6 C7 C8 -1.1(4) . . . . ?
O3 N5 C7 C6 -37.1(5) . . . . ?
O3 N5 C7 C8 134.8(4) . . . . ?
C4 N2 C3 C2 -177.4(3) . . . . ?
C4 N2 C3 C6 5.2(5) . . . . ?
O4 N5 C7 C6 144.8(4) . . . . ?
O4 N5 C7 C8 -43.2(5) . . . . ?
N4 N3 C5 C4 -178.3(3) . . . . ?
N4 N3 C6 C3 -176.2(3) . . . . ?
N4 N3 C6 C7 1.1(4) . . . . ?
C5 N3 N4 C8 176.6(3) . . . . ?
C5 N3 C6 C3 6.6(5) . . . . ?
C5 N3 C6 C7 -176.1(3) . . . . ?
N5 C7 C8 N4 -172.7(3) . . . . ?
N6 C2 C3 N2 173.3(3) . . . . ?
N6 C2 C3 C6 -10.2(7) . . . . ?
C6 N3 N4 C8 -0.7(4) . . . . ?
C6 N3 C5 C4 -1.3(6) . . . . ?
C6 C7 C8 N4 0.7(4) . . . . ?
