#------------------------------------------------------------------------------
#$Date: 2019-11-26 00:15:19 +0200 (Tue, 26 Nov 2019) $
#$Revision: 242135 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/71/4517127.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_4517127
loop_
_publ_author_name
'Xia, Honglei'
'Zhang, Wenquan'
'Jin, Yunhe'
'Song, Siwei'
'Wang, Kangcai'
'Zhang, Qinghua'
_publ_section_title
;
 Synthesis of Thermally Stable and Insensitive Energetic Materials by
 Incorporating the Tetrazole Functionality into Fused Ring
 3,6-Dinitropyrazolo-[4,3-c]Pyrazole Framework.
;
_journal_name_full               'ACS applied materials & interfaces'
_journal_paper_doi               10.1021/acsami.9b17384
_journal_year                    2019
_chemical_formula_moiety         'C6 N14 O4, 2(H2 O), 2(C H6 N3)'
_chemical_formula_sum            'C8 H16 N20 O6'
_chemical_formula_weight         488.41
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-08-22
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 93.154(12)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   3.6702(18)
_cell_length_b                   17.111(9)
_cell_length_c                   15.423(8)
_cell_measurement_reflns_used    344
_cell_measurement_temperature    173
_cell_measurement_theta_max      19.49
_cell_measurement_theta_min      4.14
_cell_volume                     967.1(9)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.992
_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  0.1080
_diffrn_reflns_av_unetI/netI     0.1392
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6904
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.288
_diffrn_reflns_theta_min         1.779
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.142
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5720
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0936 before and 0.0680 after correction. The Ratio of minimum to maximum transmission is 0.7672. The λ/2 correction factor is 0.00150.'
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.677
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.932
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         2160
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.932
_refine_ls_R_factor_all          0.1377
_refine_ls_R_factor_gt           0.0623
_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)+(0.0725P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1487
_refine_ls_wR_factor_ref         0.1908
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1060
_reflns_number_total             2160
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            am9b17384_si_005.cif
_cod_data_source_block           mo_20181175-1205-g_0m
_cod_original_cell_volume        967.1(8)
_cod_database_code               4517127
_shelxl_version_number           2013-2
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Free rotating group:
 O3(H3A,H3B)
2.b X=CH2 refined with riding coordinates:
 N10(H10A,H10B), N8(H8A,H8B), N9(H9A,H9B)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
O1 O 0.5664(8) 0.31688(14) 0.49962(16) 0.0419(8) Uani 1 1 d .
O2 O 0.9210(9) 0.29141(15) 0.61314(17) 0.0514(9) Uani 1 1 d .
N5 N 1.1320(8) 0.52228(15) 0.60481(17) 0.0275(7) Uani 1 1 d .
N6 N 1.0464(9) 0.44803(15) 0.62600(17) 0.0302(8) Uani 1 1 d .
N7 N 0.7979(9) 0.33481(16) 0.55603(19) 0.0313(7) Uani 1 1 d .
O3 O 0.9691(10) 0.6110(2) 0.94632(18) 0.0569(9) Uani 1 1 d .
H3A H 0.7801 0.6344 0.9252 0.085 Uiso 1 1 d G
H3B H 1.1288 0.6091 0.9085 0.085 Uiso 1 1 d G
N4 N 1.1288(9) 0.65092(16) 0.66653(18) 0.0346(8) Uani 1 1 d .
N1 N 1.3872(9) 0.55548(17) 0.74631(18) 0.0349(8) Uani 1 1 d .
N10 N -0.0950(9) 0.14981(17) 0.27717(19) 0.0388(9) Uani 1 1 d .
H10A H -0.1543 0.1967 0.2622 0.047 Uiso 1 1 calc R
H10B H -0.1559 0.1113 0.2436 0.047 Uiso 1 1 calc R
N8 N 0.1828(9) 0.19606(17) 0.40317(19) 0.0396(9) Uani 1 1 d .
H8A H 0.1234 0.2430 0.3882 0.047 Uiso 1 1 calc R
H8B H 0.3030 0.1877 0.4517 0.047 Uiso 1 1 calc R
N3 N 1.2522(9) 0.67988(17) 0.74294(19) 0.0392(8) Uani 1 1 d .
N2 N 1.4043(10) 0.62348(17) 0.79141(19) 0.0395(9) Uani 1 1 d .
N9 N 0.1748(9) 0.06443(17) 0.3751(2) 0.0440(9) Uani 1 1 d .
H9A H 0.1100 0.0259 0.3419 0.053 Uiso 1 1 calc R
H9B H 0.2949 0.0559 0.4237 0.053 Uiso 1 1 calc R
C2 C 1.0681(10) 0.53458(17) 0.5174(2) 0.0253(8) Uani 1 1 d .
C1 C 0.9271(10) 0.41390(18) 0.5530(2) 0.0252(8) Uani 1 1 d .
C3 C 1.2199(10) 0.57652(19) 0.6722(2) 0.0278(8) Uani 1 1 d .
C4 C 0.0894(11) 0.1369(2) 0.3516(2) 0.0308(9) 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 0.0033 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
N6 N5 C2 110.6(2) . .
N6 N5 C3 119.0(3) . .
C2 N5 C3 129.8(3) . .
C1 N6 N5 106.2(3) . .
O1 N7 C1 115.6(3) . .
O2 N7 O1 125.3(3) . .
O2 N7 C1 119.2(3) . .
H3A O3 H3B 109.5 . .
C3 N4 N3 103.1(3) . .
C3 N1 N2 102.5(3) . .
H10A N10 H10B 120.0 . .
C4 N10 H10A 120.0 . .
C4 N10 H10B 120.0 . .
H8A N8 H8B 120.0 . .
C4 N8 H8A 120.0 . .
C4 N8 H8B 120.0 . .
N2 N3 N4 109.9(3) . .
N3 N2 N1 109.2(3) . .
H9A N9 H9B 120.0 . .
C4 N9 H9A 120.0 . .
C4 N9 H9B 120.0 . .
N5 C2 C2 106.8(3) . 3_766
N5 C2 C1 148.2(3) . 3_766
C2 C2 C1 105.0(3) 3_766 3_766
N6 C1 N7 118.9(3) . .
N6 C1 C2 111.4(3) . 3_766
C2 C1 N7 129.6(3) 3_766 .
N4 C3 N5 122.5(3) . .
N1 C3 N5 122.3(3) . .
N1 C3 N4 115.2(3) . .
N10 C4 N8 120.0(3) . .
N10 C4 N9 119.8(3) . .
N8 C4 N9 120.2(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 N7 1.221(4) .
O2 N7 1.220(4) .
N5 N6 1.353(4) .
N5 C2 1.372(4) .
N5 C3 1.417(4) .
N6 C1 1.321(4) .
N7 C1 1.436(4) .
O3 H3A 0.8501 .
O3 H3B 0.8500 .
N4 N3 1.335(4) .
N4 C3 1.318(4) .
N1 N2 1.355(4) .
N1 C3 1.317(4) .
N10 H10A 0.8600 .
N10 H10B 0.8600 .
N10 C4 1.319(5) .
N8 H8A 0.8600 .
N8 H8B 0.8600 .
N8 C4 1.321(4) .
N3 N2 1.325(4) .
N9 H9A 0.8600 .
N9 H9B 0.8600 .
N9 C4 1.325(4) .
C2 C2 1.381(6) 3_766
C2 C1 1.399(4) 3_766
C1 C2 1.399(4) 3_766
