#------------------------------------------------------------------------------
#$Date: 2022-03-03 21:53:44 +0200 (Thu, 03 Mar 2022) $
#$Revision: 273231 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/93/4519321.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_4519321
loop_
_publ_author_name
'Zhang, Guojie'
'Yi, Zhenxin'
'Cheng, Guangbin'
'Yang, Wei'
'Yang, Hongwei'
_publ_section_title
;
 Polynitro-Functionalized Azopyrazole with High Performance and Low
 Sensitivity as Novel Energetic Materials.
;
_journal_issue                   8
_journal_name_full               'ACS applied materials & interfaces'
_journal_page_first              10594
_journal_page_last               10604
_journal_paper_doi               10.1021/acsami.2c00154
_journal_volume                  14
_journal_year                    2022
_chemical_formula_moiety         'C6 H2 N10 O8, 2(H2 O)'
_chemical_formula_sum            'C6 H6 N10 O10'
_chemical_formula_weight         378.21
_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   difmap
_atom_sites_solution_primary     dual
_audit_creation_date             2019-07-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 97.847(18)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.314(5)
_cell_length_b                   5.943(3)
_cell_length_c                   13.344(8)
_cell_measurement_reflns_used    655
_cell_measurement_temperature    298
_cell_measurement_theta_max      21.809
_cell_measurement_theta_min      3.083
_cell_volume                     731.7(7)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      298
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.979
_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  0.0615
_diffrn_reflns_av_unetI/netI     0.0843
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            3892
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.093
_diffrn_reflns_theta_min         3.082
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.162
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.5969
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0825 before and 0.0563 after correction. The Ratio of minimum to maximum transmission is 0.8007. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.717
_exptl_crystal_description       needle
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     130
_refine_ls_number_reflns         1577
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.1555
_refine_ls_R_factor_gt           0.0714
_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)+(0.0873P)²+0.6592P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1764
_refine_ls_wR_factor_ref         0.2201
_reflns_Friedel_coverage         0.000
_reflns_number_gt                784
_reflns_number_total             1577
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            am2c00154_si_003.cif
_cod_data_source_block           22019773zhgj10704_0m
_cod_database_code               4519321
_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   0.997
_shelx_estimated_absorpt_t_min   0.987
_olex2_refinement_description
;
1. Restrained distances
 O3-H3B = O3-H3A
 0.84 with sigma of 0.02
 N4-H4
 0.86 with sigma of 0.02
;
_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
O5 O 0.5866(4) 0.5140(6) 0.3711(3) 0.0625(10) Uani 1 1 d . . . . .
N5 N 0.5079(4) 0.0822(6) 0.4713(3) 0.0416(9) Uani 1 1 d . . . . .
N4 N 0.2503(4) 0.1495(7) 0.4704(3) 0.0466(10) Uani 1 1 d D . . . .
O4 O 0.4277(4) 0.5301(7) 0.2363(3) 0.0689(11) Uani 1 1 d . . . . .
O3 O 0.1596(5) 0.7911(7) 0.5641(4) 0.0739(13) Uani 1 1 d D . . . .
N3 N 0.1448(4) 0.2934(7) 0.4325(3) 0.0528(11) Uani 1 1 d . . . . .
O1 O 0.2063(5) 0.7845(7) 0.3086(3) 0.0750(12) Uani 1 1 d . . . . .
N1 N 0.4647(5) 0.4841(6) 0.3255(3) 0.0480(10) Uani 1 1 d . . . . .
O2 O 0.0007(4) 0.6260(8) 0.3280(4) 0.0890(15) Uani 1 1 d . . . . .
N2 N 0.1321(6) 0.6278(7) 0.3329(3) 0.0607(12) Uani 1 1 d . . . . .
C3 C 0.3795(5) 0.1987(8) 0.4419(3) 0.0435(11) Uani 1 1 d . . . . .
C2 C 0.3573(5) 0.3835(7) 0.3795(3) 0.0424(11) Uani 1 1 d . . . . .
C1 C 0.2126(5) 0.4346(8) 0.3765(3) 0.0474(12) Uani 1 1 d . . . . .
H3A H 0.082(4) 0.734(12) 0.575(5) 0.11(3) Uiso 1 1 d D . . . .
H3B H 0.218(8) 0.716(14) 0.605(6) 0.17(4) Uiso 1 1 d D . . . .
H4 H 0.230(7) 0.033(7) 0.503(4) 0.10(2) Uiso 1 1 d 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
N5 N5 C3 113.0(4) 3_656 . ?
N3 N4 H4 121(5) . . ?
C3 N4 N3 113.1(4) . . ?
C3 N4 H4 126(5) . . ?
H3A O3 H3B 99(7) . . ?
C1 N3 N4 103.4(4) . . ?
O5 N1 C2 118.1(4) . . ?
O4 N1 O5 124.7(4) . . ?
O4 N1 C2 117.2(4) . . ?
O1 N2 C1 115.3(5) . . ?
O2 N2 O1 126.2(5) . . ?
O2 N2 C1 118.4(5) . . ?
N4 C3 N5 125.5(4) . . ?
N4 C3 C2 106.2(4) . . ?
C2 C3 N5 128.3(4) . . ?
C3 C2 N1 125.2(4) . . ?
C3 C2 C1 105.0(4) . . ?
C1 C2 N1 129.6(4) . . ?
N3 C1 N2 117.6(4) . . ?
N3 C1 C2 112.3(4) . . ?
C2 C1 N2 129.6(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
O5 N1 1.225(5) . ?
N5 N5 1.262(7) 3_656 ?
N5 C3 1.391(6) . ?
N4 N3 1.348(5) . ?
N4 C3 1.343(6) . ?
N4 H4 0.85(2) . ?
O4 N1 1.224(5) . ?
O3 H3A 0.83(2) . ?
O3 H3B 0.84(2) . ?
N3 C1 1.339(6) . ?
O1 N2 1.229(6) . ?
N1 C2 1.440(6) . ?
O2 N2 1.217(5) . ?
N2 C1 1.449(6) . ?
C3 C2 1.377(6) . ?
C2 C1 1.377(7) . ?
