#------------------------------------------------------------------------------
#$Date: 2024-01-06 12:01:44 +0200 (Sat, 06 Jan 2024) $
#$Revision: 288913 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/00/1570008.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_1570008
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         'C7 H2 N10 O12'
_chemical_formula_sum            'C7 H2 N10 O12'
_chemical_formula_weight         418.19
_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     dual
_audit_creation_date             2022-06-01
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-09-19 deposited with the CCDC.	2023-09-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 113.671(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.4453(12)
_cell_length_b                   8.5038(5)
_cell_length_c                   12.4151(11)
_cell_measurement_reflns_used    2810
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      27.052
_cell_measurement_theta_min      2.795
_cell_volume                     1493.5(2)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0720
_diffrn_reflns_av_unetI/netI     0.0478
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            18890
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.473
_diffrn_reflns_theta_min         2.795
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.179
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6938
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1216 before and 0.0802 after correction.
The Ratio of minimum to maximum transmission is 0.9305.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.860
_exptl_crystal_description       block
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.429
_refine_diff_density_min         -0.324
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3416
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0684
_refine_ls_R_factor_gt           0.0471
_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)+(0.0445P)²+1.0643P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1076
_refine_ls_wR_factor_ref         0.1284
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2529
_reflns_number_total             3416
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3mh01381b2.cif
_cod_data_source_block           mo_20220601li_dyq_xm_0m
_cod_depositor_comments
'Adding full bibliography for 1570008--1570010.cif.'
_cod_database_code               1570008
_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   0.979
_shelx_estimated_absorpt_t_min   0.974
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C7(H7)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
O1 O 0.64221(12) 0.31231(19) 0.51188(15) 0.0327(4) Uani 1 1 d . . . . .
O2 O 0.56408(12) 0.16421(19) 0.58481(18) 0.0405(5) Uani 1 1 d . . . . .
O3 O 0.70640(13) 0.1854(2) 0.80582(17) 0.0409(5) Uani 1 1 d . . . . .
O4 O 0.74650(13) 0.4228(2) 0.87166(15) 0.0413(5) Uani 1 1 d . . . . .
O5 O 0.54215(14) 0.4139(2) 0.80132(18) 0.0446(5) Uani 1 1 d . . . . .
O6 O 0.46337(12) 0.4154(2) 0.61126(18) 0.0416(5) Uani 1 1 d . . . . .
O7 O 0.86236(11) 0.83123(19) 0.63453(17) 0.0349(4) Uani 1 1 d . . . . .
O8 O 0.76296(12) 1.01564(18) 0.62493(17) 0.0377(4) Uani 1 1 d . . . . .
O9 O 0.87226(14) 0.6113(2) 0.39654(17) 0.0435(5) Uani 1 1 d . . . . .
O10 O 0.74438(13) 0.6838(2) 0.41521(15) 0.0393(5) Uani 1 1 d . . . . .
O11 O 0.99899(13) 0.1205(2) 0.6798(2) 0.0479(5) Uani 1 1 d . . . . .
O12 O 0.94868(14) 0.1517(2) 0.8193(2) 0.0511(6) Uani 1 1 d . . . . .
N1 N 0.59568(13) 0.6720(2) 0.66859(17) 0.0253(4) Uani 1 1 d . . . . .
N2 N 0.65206(12) 0.5503(2) 0.66031(16) 0.0217(4) Uani 1 1 d . . . . .
N3 N 0.60982(13) 0.2794(2) 0.58288(18) 0.0274(4) Uani 1 1 d . . . . .
N4 N 0.70236(14) 0.3271(2) 0.79929(17) 0.0294(4) Uani 1 1 d . . . . .
N5 N 0.53433(14) 0.4097(2) 0.7008(2) 0.0303(5) Uani 1 1 d . . . . .
N6 N 0.78629(13) 0.8777(2) 0.63152(17) 0.0259(4) Uani 1 1 d . . . . .
N7 N 0.81712(13) 0.6067(2) 0.44476(17) 0.0272(4) Uani 1 1 d . . . . .
N8 N 0.83754(13) 0.3835(2) 0.70421(17) 0.0255(4) Uani 1 1 d . . . . .
N9 N 0.89721(13) 0.3143(2) 0.66429(18) 0.0277(4) Uani 1 1 d . . . . .
N10 N 0.95385(14) 0.1824(2) 0.7278(2) 0.0373(5) Uani 1 1 d . . . . .
C1 C 0.63723(15) 0.7997(2) 0.6545(2) 0.0253(5) Uani 1 1 d . . . . .
H1 H 0.614138 0.903245 0.654399 0.030 Uiso 1 1 calc R U . . .
C2 C 0.72031(15) 0.7636(2) 0.63953(19) 0.0220(4) Uani 1 1 d . . . . .
C3 C 0.72981(14) 0.6032(2) 0.64276(18) 0.0211(4) Uani 1 1 d . . . . .
C4 C 0.62757(15) 0.3982(2) 0.6831(2) 0.0234(5) Uani 1 1 d . . . . .
C5 C 0.80084(14) 0.5003(2) 0.62922(19) 0.0223(4) Uani 1 1 d . . . . .
C6 C 0.83930(14) 0.5026(2) 0.54383(19) 0.0228(4) Uani 1 1 d . . . . .
C7 C 0.90219(15) 0.3809(3) 0.5683(2) 0.0262(5) Uani 1 1 d . . . . .
H7 H 0.940152 0.350669 0.527663 0.031 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 0.0033 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
C1 N1 N2 104.71(17) . . ?
N1 N2 C4 116.41(17) . . ?
C3 N2 N1 112.46(17) . . ?
C3 N2 C4 130.73(18) . . ?
O1 N3 O2 128.1(2) . . ?
O1 N3 C4 116.47(17) . . ?
O2 N3 C4 115.5(2) . . ?
O3 N4 C4 116.55(19) . . ?
O4 N4 O3 128.8(2) . . ?
O4 N4 C4 114.57(18) . . ?
O5 N5 O6 128.9(2) . . ?
O5 N5 C4 115.93(19) . . ?
O6 N5 C4 115.2(2) . . ?
O7 N6 C2 118.51(18) . . ?
O8 N6 O7 124.44(19) . . ?
O8 N6 C2 117.02(19) . . ?
O9 N7 O10 124.9(2) . . ?
O9 N7 C6 117.64(19) . . ?
O10 N7 C6 117.4(2) . . ?
C5 N8 N9 103.46(19) . . ?
N8 N9 N10 119.5(2) . . ?
N8 N9 C7 115.60(18) . . ?
C7 N9 N10 124.8(2) . . ?
O11 N10 N9 114.3(2) . . ?
O12 N10 O11 130.2(2) . . ?
O12 N10 N9 115.4(2) . . ?
N1 C1 H1 124.4 . . ?
N1 C1 C2 111.13(19) . . ?
C2 C1 H1 124.4 . . ?
C1 C2 N6 124.96(19) . . ?
C3 C2 N6 127.04(19) . . ?
C3 C2 C1 107.84(19) . . ?
N2 C3 C5 124.29(18) . . ?
C2 C3 N2 103.84(18) . . ?
C2 C3 C5 131.8(2) . . ?
N2 C4 N3 114.55(19) . . ?
N2 C4 N4 112.47(17) . . ?
N2 C4 N5 108.14(17) . . ?
N3 C4 N4 108.53(16) . . ?
N3 C4 N5 106.42(16) . . ?
N5 C4 N4 106.24(17) . . ?
N8 C5 C3 119.8(2) . . ?
N8 C5 C6 110.43(19) . . ?
C6 C5 C3 129.80(19) . . ?
C5 C6 N7 128.58(19) . . ?
C7 C6 N7 124.0(2) . . ?
C7 C6 C5 107.4(2) . . ?
N9 C7 C6 103.1(2) . . ?
N9 C7 H7 128.4 . . ?
C6 C7 H7 128.4 . . ?
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 N3 1.208(3) . ?
O2 N3 1.213(2) . ?
O3 N4 1.208(3) . ?
O4 N4 1.201(3) . ?
O5 N5 1.206(3) . ?
O6 N5 1.208(3) . ?
O7 N6 1.226(2) . ?
O8 N6 1.220(2) . ?
O9 N7 1.223(3) . ?
O10 N7 1.223(2) . ?
O11 N10 1.206(3) . ?
O12 N10 1.198(3) . ?
N1 N2 1.383(2) . ?
N1 C1 1.308(3) . ?
N2 C3 1.379(3) . ?
N2 C4 1.408(3) . ?
N3 C4 1.540(3) . ?
N4 C4 1.563(3) . ?
N5 C4 1.544(3) . ?
N6 C2 1.439(3) . ?
N7 C6 1.441(3) . ?
N8 N9 1.345(3) . ?
N8 C5 1.323(3) . ?
N9 N10 1.446(3) . ?
N9 C7 1.349(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.402(3) . ?
C2 C3 1.371(3) . ?
C3 C5 1.465(3) . ?
C5 C6 1.408(3) . ?
C6 C7 1.367(3) . ?
C7 H7 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
O1 N3 C4 N2 19.3(3) . . . . ?
O1 N3 C4 N4 -107.3(2) . . . . ?
O1 N3 C4 N5 138.74(18) . . . . ?
O2 N3 C4 N2 -160.12(18) . . . . ?
O2 N3 C4 N4 73.3(2) . . . . ?
O2 N3 C4 N5 -40.7(2) . . . . ?
O3 N4 C4 N2 -154.9(2) . . . . ?
O3 N4 C4 N3 -27.1(3) . . . . ?
O3 N4 C4 N5 87.0(2) . . . . ?
O4 N4 C4 N2 27.1(3) . . . . ?
O4 N4 C4 N3 154.85(19) . . . . ?
O4 N4 C4 N5 -91.1(2) . . . . ?
O5 N5 C4 N2 -98.2(2) . . . . ?
O5 N5 C4 N3 138.26(19) . . . . ?
O5 N5 C4 N4 22.7(2) . . . . ?
O6 N5 C4 N2 80.9(2) . . . . ?
O6 N5 C4 N3 -42.6(2) . . . . ?
O6 N5 C4 N4 -158.14(18) . . . . ?
O7 N6 C2 C1 170.2(2) . . . . ?
O7 N6 C2 C3 -4.6(3) . . . . ?
O8 N6 C2 C1 -8.1(3) . . . . ?
O8 N6 C2 C3 177.1(2) . . . . ?
O9 N7 C6 C5 164.4(2) . . . . ?
O9 N7 C6 C7 -17.9(3) . . . . ?
O10 N7 C6 C5 -15.6(3) . . . . ?
O10 N7 C6 C7 162.0(2) . . . . ?
N1 N2 C3 C2 -0.3(2) . . . . ?
N1 N2 C3 C5 -179.15(19) . . . . ?
N1 N2 C4 N3 123.83(19) . . . . ?
N1 N2 C4 N4 -111.6(2) . . . . ?
N1 N2 C4 N5 5.4(3) . . . . ?
N1 C1 C2 N6 -174.7(2) . . . . ?
N1 C1 C2 C3 1.0(3) . . . . ?
N2 N1 C1 C2 -1.2(2) . . . . ?
N2 C3 C5 N8 -47.8(3) . . . . ?
N2 C3 C5 C6 131.4(2) . . . . ?
N6 C2 C3 N2 175.2(2) . . . . ?
N6 C2 C3 C5 -6.1(4) . . . . ?
N7 C6 C7 N9 -177.72(19) . . . . ?
N8 N9 N10 O11 174.1(2) . . . . ?
N8 N9 N10 O12 -5.9(3) . . . . ?
N8 N9 C7 C6 -0.7(3) . . . . ?
N8 C5 C6 N7 178.1(2) . . . . ?
N8 C5 C6 C7 0.1(2) . . . . ?
N9 N8 C5 C3 178.86(18) . . . . ?
N9 N8 C5 C6 -0.5(2) . . . . ?
N10 N9 C7 C6 -177.51(19) . . . . ?
C1 N1 N2 C3 0.9(2) . . . . ?
C1 N1 N2 C4 174.44(19) . . . . ?
C1 C2 C3 N2 -0.4(2) . . . . ?
C1 C2 C3 C5 178.3(2) . . . . ?
C2 C3 C5 N8 133.7(2) . . . . ?
C2 C3 C5 C6 -47.0(4) . . . . ?
C3 N2 C4 N3 -64.1(3) . . . . ?
C3 N2 C4 N4 60.4(3) . . . . ?
C3 N2 C4 N5 177.4(2) . . . . ?
C3 C5 C6 N7 -1.2(4) . . . . ?
C3 C5 C6 C7 -179.2(2) . . . . ?
C4 N2 C3 C2 -172.6(2) . . . . ?
C4 N2 C3 C5 8.5(4) . . . . ?
C5 N8 N9 N10 177.77(18) . . . . ?
C5 N8 N9 C7 0.8(2) . . . . ?
C5 C6 C7 N9 0.3(2) . . . . ?
C7 N9 N10 O11 -9.2(3) . . . . ?
C7 N9 N10 O12 170.8(2) . . . . ?
