#------------------------------------------------------------------------------
#$Date: 2019-10-28 04:57:52 +0200 (Mon, 28 Oct 2019) $
#$Revision: 219636 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/44/4514447.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_4514447
loop_
_publ_author_name
'Ma, Jinchao'
'Tang, Jie'
'Yang, Hongwei'
'Yi, Zhenxin'
'Wu, Ganggang'
'Zhu, Shunguan'
'Zhang, Wenchao'
'Li, Yanchun'
'Cheng, Guangbin'
_publ_section_title
;
 Polynitro-Functionalized Triazolylfurazanate Triaminoguanidine: Novel
 Green Primary Explosive with Insensitive Nature.
;
_journal_issue                   29
_journal_name_full               'ACS applied materials & interfaces'
_journal_page_first              26053
_journal_page_last               26059
_journal_paper_doi               10.1021/acsami.9b08363
_journal_volume                  11
_journal_year                    2019
_chemical_formula_moiety         '2(C5 H2 N9 O7), 1.5(H4 O2), 2(C H8 N5)'
_chemical_formula_sum            'C12 H26 N28 O17'
_chemical_formula_weight         834.61
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-01-25
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 97.532(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.537(3)
_cell_length_b                   6.5494(10)
_cell_length_c                   27.351(4)
_cell_measurement_reflns_used    3423
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.209
_cell_measurement_theta_min      2.343
_cell_volume                     3114.3(8)
_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      100.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0827
_diffrn_reflns_av_unetI/netI     0.0872
_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       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            5414
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.010
_diffrn_reflns_theta_max         25.010
_diffrn_reflns_theta_min         2.253
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.161
_exptl_absorpt_correction_T_max  0.745373
_exptl_absorpt_correction_T_min  0.560847
_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 30434 reflections, Rint = 0.2018
 (13627 with I > 3sig(I), Rint = 0.1714)
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.780
_exptl_crystal_description       needle
_exptl_crystal_F_000             1720
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.579
_refine_diff_density_min         -0.507
_refine_diff_density_rms         0.128
_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     266
_refine_ls_number_reflns         2796
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.1161
_refine_ls_R_factor_gt           0.0978
_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)+(0.1276P)²+45.3361P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2552
_refine_ls_wR_factor_ref         0.2713
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2240
_reflns_number_total             2796
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            am9b08363_si_002.cif
_cod_data_source_block           tj-mjc
_cod_original_cell_volume        3114.4(8)
_cod_database_code               4514447
_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   0.995
_shelx_estimated_absorpt_t_min   0.990
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.9130(19)
 0.0870(19)
2. Fixed Uiso
 At 1.2 times of:
  All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
3. Others
 Fixed Sof: H9A(0.5) H9B(0.5)
4.a Free rotating group:
 O9(H9A,H9B), O8(H8A,H8B)
4.b Rotating group:
 N12(H12A,H12B)
4.c Aromatic/amide H refined with riding coordinates:
 N7(H7), N6(H6), N11(H11), N13(H13)
4.d X=CH2 refined with riding coordinates:
 N10(H10A,H10B), N14(H14A,H14B)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
O2 O 0.40720(19) 0.8269(5) 0.52400(12) 0.0169(8) Uani 1 1 d . . .
O4 O 0.8356(2) 0.3712(6) 0.60703(12) 0.0187(8) Uani 1 1 d . . .
O3 O 0.56099(19) 0.7477(6) 0.36557(12) 0.0199(9) Uani 1 1 d . . .
O6 O 0.5950(2) 0.6204(6) 0.60965(13) 0.0216(9) Uani 1 1 d . . .
O5 O 0.7998(2) 0.4224(7) 0.67893(13) 0.0269(10) Uani 1 1 d . . .
O1 O 0.3936(2) 0.8842(6) 0.44481(13) 0.0229(9) Uani 1 1 d . . .
O9 O 0.500000 0.4352(9) 0.750000 0.0239(13) Uani 1 2 d S T P
H9A H 0.501173 0.503896 0.722889 0.036 Uiso 0.5 1 d G . .
H9B H 0.528430 0.505722 0.772390 0.036 Uiso 0.5 1 d G . .
O8 O 0.4797(2) 0.7303(6) 0.67400(14) 0.0252(9) Uani 1 1 d . . .
H8A H 0.435727 0.753841 0.656096 0.038 Uiso 1 1 d G . .
H8B H 0.511466 0.708818 0.652626 0.038 Uiso 1 1 d G . .
O7 O 0.6621(2) 0.5443(7) 0.67941(13) 0.0301(10) Uani 1 1 d . . .
N7 N 0.6455(2) 0.5950(6) 0.52700(14) 0.0132(9) Uani 1 1 d . . .
H7 H 0.602355 0.637445 0.536838 0.016 Uiso 1 1 calc R . .
N6 N 0.7586(2) 0.4727(6) 0.52464(14) 0.0131(9) Uani 1 1 d . . .
H6 H 0.804159 0.418257 0.533656 0.016 Uiso 1 1 calc R . .
N3 N 0.5036(2) 0.7965(7) 0.39462(15) 0.0160(9) Uani 1 1 d . . .
N9 N 0.6566(3) 0.5539(7) 0.63428(15) 0.0184(10) Uani 1 1 d . . .
N5 N 0.7300(2) 0.5185(6) 0.47681(14) 0.0140(9) Uani 1 1 d . . .
N10 N 0.7262(2) 0.9957(7) 0.63251(15) 0.0167(10) Uani 1 1 d . . .
H10A H 0.697637 1.021622 0.604274 0.020 Uiso 1 1 calc R . .
H10B H 0.774775 0.961415 0.632970 0.020 Uiso 1 1 calc R . .
N2 N 0.5036(2) 0.7509(7) 0.48458(15) 0.0161(10) Uani 1 1 d . . .
N1 N 0.4327(2) 0.8255(7) 0.48350(15) 0.0173(10) Uani 1 1 d . . .
N4 N 0.6241(2) 0.6647(7) 0.39379(15) 0.0181(10) Uani 1 1 d . . .
N11 N 0.7408(2) 0.9736(7) 0.71720(16) 0.0195(10) Uani 1 1 d . . .
H11 H 0.723036 0.983319 0.745739 0.023 Uiso 1 1 calc R . .
N8 N 0.7869(2) 0.4287(7) 0.63330(15) 0.0184(10) Uani 1 1 d . . .
N13 N 0.6229(2) 1.0599(7) 0.67421(16) 0.0193(10) Uani 1 1 d . . .
H13 H 0.594217 1.091113 0.646365 0.023 Uiso 1 1 calc R . .
N12 N 0.8186(2) 0.9202(8) 0.71420(16) 0.0226(11) Uani 1 1 d . . .
H12A H 0.830794 0.798826 0.728531 0.027 Uiso 1 1 d GR . .
H12B H 0.827173 0.910992 0.682630 0.027 Uiso 1 1 d GR . .
N14 N 0.5916(3) 1.0640(8) 0.71940(16) 0.0245(11) Uani 1 1 d . . .
H14A H 0.620589 1.032534 0.747099 0.029 Uiso 1 1 calc R . .
H14B H 0.543096 1.097902 0.719753 0.029 Uiso 1 1 calc R . .
C3 C 0.6617(3) 0.5907(7) 0.47983(16) 0.0120(10) Uani 1 1 d . . .
C1 C 0.5322(3) 0.7440(8) 0.44027(18) 0.0146(11) Uani 1 1 d . . .
C5 C 0.7169(3) 0.4997(8) 0.60825(18) 0.0141(11) Uani 1 1 d . . .
C6 C 0.6958(3) 1.0085(8) 0.67451(18) 0.0163(11) Uani 1 1 d . . .
C4 C 0.7082(3) 0.5217(8) 0.55627(17) 0.0120(10) Uani 1 1 d . . .
C2 C 0.6075(3) 0.6640(8) 0.43892(17) 0.0150(11) 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
N4 O3 N3 111.0(3) . .
H9A O9 H9A 117.7 . 2_656
H9A O9 H9B 104.5 . .
H9A O9 H9B 104.5 2_656 2_656
H9A O9 H9B 36.9 . 2_656
H9B O9 H9A 36.9 . 2_656
H9B O9 H9B 115.9 . 2_656
H8A O8 H8B 104.4 . .
C3 N7 H7 126.3 . .
C3 N7 C4 107.3(4) . .
C4 N7 H7 126.3 . .
N5 N6 H6 124.2 . .
C4 N6 H6 124.2 . .
C4 N6 N5 111.7(4) . .
C1 N3 O3 105.3(4) . .
O6 N9 C5 117.7(4) . .
O7 N9 O6 119.9(4) . .
O7 N9 C5 122.4(4) . .
C3 N5 N6 104.1(4) . .
H10A N10 H10B 120.0 . .
C6 N10 H10A 120.0 . .
C6 N10 H10B 120.0 . .
N1 N2 C1 116.1(4) . .
O2 N1 N2 115.1(4) . .
O1 N1 O2 122.1(4) . .
O1 N1 N2 122.8(4) . .
C2 N4 O3 105.7(4) . .
N12 N11 H11 121.6 . .
C6 N11 H11 121.6 . .
C6 N11 N12 116.8(4) . .
O4 N8 C5 116.1(4) . .
O5 N8 O4 121.5(4) . .
O5 N8 C5 122.3(4) . .
N14 N13 H13 120.5 . .
C6 N13 H13 120.5 . .
C6 N13 N14 119.0(4) . .
N11 N12 H12A 111.5 . .
N11 N12 H12B 110.8 . .
H12A N12 H12B 107.4 . .
N13 N14 H14A 120.0 . .
N13 N14 H14B 120.0 . .
H14A N14 H14B 120.0 . .
N7 C3 C2 121.9(4) . .
N5 C3 N7 112.2(4) . .
N5 C3 C2 125.9(4) . .
N3 C1 N2 133.2(5) . .
N3 C1 C2 107.9(4) . .
N2 C1 C2 118.8(4) . .
N9 C5 N8 120.5(4) . .
N9 C5 C4 119.7(4) . .
N8 C5 C4 119.7(4) . .
N10 C6 N11 119.0(5) . .
N13 C6 N10 120.5(4) . .
N13 C6 N11 120.5(5) . .
N7 C4 C5 126.8(4) . .
N6 C4 N7 104.7(4) . .
N6 C4 C5 128.5(4) . .
N4 C2 C3 121.8(4) . .
N4 C2 C1 110.2(4) . .
C1 C2 C3 128.1(4) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O2 N1 1.248(5) .
O4 N8 1.244(6) .
O3 N3 1.399(5) .
O3 N4 1.375(5) .
O6 N9 1.272(6) .
O5 N8 1.240(5) .
O1 N1 1.244(5) .
O9 H9A 0.87(14) 2_656
O9 H9A 0.8699 .
O9 H9B 0.8701 .
O9 H9B 0.87(14) 2_656
O8 H8A 0.8712 .
O8 H8B 0.8703 .
O7 N9 1.227(5) .
N7 H7 0.8800 .
N7 C3 1.357(6) .
N7 C4 1.360(6) .
N6 H6 0.8800 .
N6 N5 1.372(5) .
N6 C4 1.354(6) .
N3 C1 1.328(6) .
N9 C5 1.396(7) .
N5 C3 1.300(6) .
N10 H10A 0.8800 .
N10 H10B 0.8800 .
N10 C6 1.330(7) .
N2 N1 1.332(6) .
N2 C1 1.372(6) .
N4 C2 1.305(6) .
N11 H11 0.8800 .
N11 N12 1.421(6) .
N11 C6 1.340(6) .
N8 C5 1.404(6) .
N13 H13 0.8800 .
N13 N14 1.417(6) .
N13 C6 1.322(7) .
N12 H12A 0.8997 .
N12 H12B 0.8976 .
N14 H14A 0.8800 .
N14 H14B 0.8800 .
C3 C2 1.451(6) .
C1 C2 1.426(7) .
C5 C4 1.417(7) .
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 O8 0.87 2.00 2.827(5) 158.5 . yes
O9 H9B O8 0.87 2.09 2.827(5) 141.3 2_656 yes
N7 H7 N2 0.88 2.22 2.797(6) 122.5 . yes
N6 H6 O2 0.88 1.95 2.777(5) 155.2 3_545 yes
N10 H10A O1 0.88 2.04 2.887(5) 160.1 5_676 yes
N13 H13 N3 0.88 2.06 2.873(6) 153.6 5_676 yes
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.9130(19)
2 0.0870(19)
