#------------------------------------------------------------------------------
#$Date: 2022-03-03 21:54:49 +0200 (Thu, 03 Mar 2022) $
#$Revision: 273234 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/93/4519324.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_4519324
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 N10 O8, 2(H2 O), 2(H4 N)'
_chemical_formula_sum            'C6 H12 N12 O10'
_chemical_formula_weight         412.28
_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   difmap
_atom_sites_solution_primary     dual
_audit_creation_date             2019-07-19
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                101.457(3)
_cell_angle_beta                 92.636(3)
_cell_angle_gamma                99.304(3)
_cell_formula_units_Z            2
_cell_length_a                   7.1996(7)
_cell_length_b                   10.1924(10)
_cell_length_c                   11.2601(11)
_cell_measurement_reflns_used    1029
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.288
_cell_measurement_theta_min      2.473
_cell_volume                     796.55(14)
_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      173.0
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.974
_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
_diffrn_reflns_av_unetI/netI     0.2106
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_number            3573
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_min         2.472
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.160
_exptl_absorpt_correction_T_max  0.745553
_exptl_absorpt_correction_T_min  0.627631
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.

Final HKLF 4 output contains 12124 reflections, Rint = 0.0712
 (4627 with I > 3sig(I), Rint = 0.0444)
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.719
_exptl_crystal_description       needle
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         3573
_refine_ls_number_restraints     14
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.1825
_refine_ls_R_factor_gt           0.0862
_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)+(0.0828P)²+0.3720P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1728
_refine_ls_wR_factor_ref         0.2015
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1869
_reflns_number_total             3573
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            am2c00154_si_005.cif
_cod_data_source_block           22019795_0m_4
_cod_database_code               4519324
_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. Fixed Uiso
 At 1.5 times of:
  All N(H,H) groups, All O(H) groups, All O(H,H) groups
2. Restrained distances
 O10-H10B
 0.84 with sigma of 0.02
 H10B-H10A
 1.46 with sigma of 0.02
 N12-H12A \\sim N12-H12B \\sim N12-H12C \\sim N12-H12D
 with sigma of 0.02
 N11-H11C \\sim N11-H11D \\sim N11-H11B \\sim N11-H11A
 with sigma of 0.02
3.a Free rotating group:
 O9(H9A,H9B), O10(H10A), N11(H11A,H11B), N12(H12A,H12B)
;
_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
O2 O 0.3057(4) 0.5168(3) 0.9206(3) 0.0344(8) Uani 1 1 d . . . . .
O9 O 0.2920(5) 0.6497(3) 0.1817(3) 0.0349(8) Uani 1 1 d . . . . .
H9A H 0.307551 0.569834 0.192467 0.052 Uiso 1 1 d G . . . .
H9B H 0.203194 0.632914 0.122952 0.052 Uiso 1 1 d G . . . .
O7 O 0.4522(5) 0.0153(3) 0.3040(3) 0.0410(9) Uani 1 1 d . . . . .
O1 O 0.1759(5) 0.3646(3) 0.7639(3) 0.0410(9) Uani 1 1 d . . . . .
O3 O 0.0254(4) 0.6779(3) 0.9882(3) 0.0393(9) Uani 1 1 d . . . . .
O8 O 0.4562(5) 0.0458(3) 0.1190(3) 0.0454(9) Uani 1 1 d . . . . .
N3 N 0.1236(5) 0.7865(3) 0.7228(3) 0.0254(8) Uani 1 1 d . . . . .
N6 N 0.2446(5) 0.5049(3) 0.4452(3) 0.0259(8) Uani 1 1 d . . . . .
N4 N 0.1614(5) 0.7110(3) 0.6172(3) 0.0239(8) Uani 1 1 d . . . . .
N1 N 0.2214(5) 0.4834(3) 0.8195(3) 0.0263(8) Uani 1 1 d . . . . .
N5 N 0.2436(5) 0.4842(3) 0.5517(3) 0.0239(8) Uani 1 1 d . . . . .
O10 O 0.0267(5) 0.0600(4) 0.7773(3) 0.0485(9) Uani 1 1 d D . . . .
H10A H 0.113810 0.062563 0.726308 0.073 Uiso 1 1 d DG . . . .
O5 O 0.1838(5) 0.1302(3) 0.4931(3) 0.0447(9) Uani 1 1 d . . . . .
N11 N 0.1643(6) 0.8084(4) 0.3898(3) 0.0289(9) Uani 1 1 d D . . . .
H11A H 0.061416 0.830893 0.362702 0.043 Uiso 1 1 d DG . . . .
H11B H 0.195552 0.751807 0.328529 0.043 Uiso 1 1 d DG . . . .
O4 O 0.0912(6) 0.8847(4) 0.9630(3) 0.0523(10) Uani 1 1 d . . . . .
O6 O 0.4594(5) 0.2409(4) 0.5619(3) 0.0511(10) Uani 1 1 d . . . . .
N10 N 0.4292(5) 0.0813(4) 0.2252(4) 0.0304(9) Uani 1 1 d . . . . .
N8 N 0.3613(5) 0.2930(3) 0.1859(3) 0.0285(8) Uani 1 1 d . . . . .
N9 N 0.3266(5) 0.2097(4) 0.4862(3) 0.0279(8) Uani 1 1 d . . . . .
N2 N 0.0814(5) 0.7618(4) 0.9276(3) 0.0315(9) Uani 1 1 d . . . . .
N7 N 0.3138(5) 0.4064(3) 0.2488(3) 0.0270(8) Uani 1 1 d . . . . .
N12 N 0.6088(6) 0.7837(4) 0.0834(4) 0.0347(9) Uani 1 1 d D . . . .
H12A H 0.723277 0.803259 0.117958 0.052 Uiso 1 1 d DG . . . .
H12B H 0.611875 0.755165 0.005496 0.052 Uiso 1 1 d DG . . . .
C3 C 0.1935(5) 0.5900(4) 0.6371(3) 0.0196(9) Uani 1 1 d . . . . .
C2 C 0.1764(5) 0.5866(4) 0.7588(4) 0.0225(9) Uani 1 1 d . . . . .
C1 C 0.1343(5) 0.7127(4) 0.8086(3) 0.0225(9) Uani 1 1 d . . . . .
C5 C 0.3350(5) 0.2700(4) 0.3793(4) 0.0229(9) Uani 1 1 d . . . . .
C4 C 0.2968(5) 0.3952(4) 0.3656(4) 0.0230(9) Uani 1 1 d . . . . .
C6 C 0.3751(5) 0.2108(4) 0.2650(4) 0.0247(9) Uani 1 1 d . . . . .
H12C H 0.572(7) 0.862(3) 0.084(4) 0.046(15) Uiso 1 1 d D . . . .
H12D H 0.523(6) 0.732(5) 0.116(5) 0.061(18) Uiso 1 1 d D . . . .
H11C H 0.160(7) 0.774(5) 0.454(3) 0.061(17) Uiso 1 1 d D . . . .
H11D H 0.242(6) 0.884(3) 0.403(5) 0.07(2) Uiso 1 1 d D . . . .
H10B H 0.024(18) -0.001(12) 0.819(12) 0.42(11) 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
H9A O9 H9B 104.5 . . ?
C1 N3 N4 107.5(3) . . ?
N5 N6 C4 110.7(3) . . ?
N3 N4 C3 108.6(3) . . ?
O2 N1 O1 123.6(3) . . ?
O2 N1 C2 119.3(3) . . ?
O1 N1 C2 117.0(4) . . ?
N6 N5 C3 114.2(3) . . ?
H10A O10 H10B 115.9 . . ?
H11A N11 H11B 104.5 . . ?
H11A N11 H11C 117.7 . . ?
H11A N11 H11D 102.2 . . ?
H11B N11 H11C 110.6 . . ?
H11B N11 H11D 110.1 . . ?
H11C N11 H11D 111(5) . . ?
O7 N10 C6 116.6(4) . . ?
O8 N10 O7 124.6(4) . . ?
O8 N10 C6 118.7(3) . . ?
N7 N8 C6 106.5(3) . . ?
O5 N9 C5 117.0(4) . . ?
O6 N9 O5 124.2(4) . . ?
O6 N9 C5 118.9(4) . . ?
O3 N2 C1 117.8(4) . . ?
O4 N2 O3 123.6(4) . . ?
O4 N2 C1 118.6(4) . . ?
N8 N7 C4 109.4(3) . . ?
H12A N12 H12B 109.5 . . ?
H12A N12 H12C 106.2 . . ?
H12A N12 H12D 117.9 . . ?
H12B N12 H12C 100.0 . . ?
H12B N12 H12D 113.1 . . ?
H12C N12 H12D 108(5) . . ?
N4 C3 N5 126.6(3) . . ?
N4 C3 C2 109.4(3) . . ?
C2 C3 N5 123.9(3) . . ?
C3 C2 N1 126.7(3) . . ?
C1 C2 N1 128.8(4) . . ?
C1 C2 C3 103.9(3) . . ?
N3 C1 N2 119.8(3) . . ?
N3 C1 C2 110.6(3) . . ?
C2 C1 N2 129.1(3) . . ?
C4 C5 N9 129.3(4) . . ?
C6 C5 N9 127.1(3) . . ?
C6 C5 C4 103.5(3) . . ?
N7 C4 N6 117.3(3) . . ?
N7 C4 C5 109.2(3) . . ?
C5 C4 N6 133.5(4) . . ?
N8 C6 N10 120.0(4) . . ?
N8 C6 C5 111.4(3) . . ?
C5 C6 N10 128.5(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
O2 N1 1.223(4) . ?
O9 H9A 0.8701 . ?
O9 H9B 0.8701 . ?
O7 N10 1.235(4) . ?
O1 N1 1.232(5) . ?
O3 N2 1.227(4) . ?
O8 N10 1.212(4) . ?
N3 N4 1.347(5) . ?
N3 C1 1.344(5) . ?
N6 N5 1.259(4) . ?
N6 C4 1.400(5) . ?
N4 C3 1.351(5) . ?
N1 C2 1.432(5) . ?
N5 C3 1.401(5) . ?
O10 H10A 0.8701 . ?
O10 H10B 0.84(2) . ?
O5 N9 1.218(4) . ?
N11 H11A 0.8695 . ?
N11 H11B 0.8705 . ?
N11 H11C 0.865(17) . ?
N11 H11D 0.859(17) . ?
O4 N2 1.226(5) . ?
O6 N9 1.209(5) . ?
N10 C6 1.430(5) . ?
N8 N7 1.334(5) . ?
N8 C6 1.349(5) . ?
N9 C5 1.455(5) . ?
N2 C1 1.426(5) . ?
N7 C4 1.352(5) . ?
N12 H12A 0.8701 . ?
N12 H12B 0.8701 . ?
N12 H12C 0.876(17) . ?
N12 H12D 0.885(17) . ?
C3 C2 1.388(5) . ?
C2 C1 1.384(5) . ?
C5 C4 1.385(5) . ?
C5 C6 1.374(6) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O9 H9A N7 0.87 1.90 2.758(4) 166.9 . yes
N11 H11B O9 0.87 1.99 2.850(5) 170.5 . yes
N12 H12D O9 0.885(17) 1.98(2) 2.849(5) 166(5) . yes
