#------------------------------------------------------------------------------
#$Date: 2020-07-02 00:15:40 +0300 (Thu, 02 Jul 2020) $
#$Revision: 253624 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/78/4517824.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_4517824
loop_
_publ_author_name
'Yu, Qiong'
'Yang, Hongwei'
'Imler, Gregory H.'
'Parrish, Damon A.'
'Cheng, Guangbin'
'Shreeve, Jean'ne M.'
_publ_section_title
;
 Derivatives of 3,6-Bis(3-aminofurazan-4-ylamino)-1,2,4,5-tetrazine:
 Excellent Energetic Properties with Lower Sensitivities.
;
_journal_name_full               'ACS applied materials & interfaces'
_journal_paper_doi               10.1021/acsami.0c08526
_journal_year                    2020
_chemical_formula_moiety         'C10 H8 N18 O14, 6(C3 H8 O)'
_chemical_formula_sum            'C28 H56 N18 O20'
_chemical_formula_weight         964.91
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                97.585(4)
_cell_angle_beta                 90.245(4)
_cell_angle_gamma                114.797(3)
_cell_formula_units_Z            1
_cell_length_a                   9.7943(11)
_cell_length_b                   10.4746(13)
_cell_length_c                   13.0589(18)
_cell_measurement_reflns_used    1587
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      22.94
_cell_measurement_theta_min      3.55
_cell_volume                     1202.9(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'PHOTON100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_monochromator  'TRIUMPH curved crystal monochromator'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0660
_diffrn_reflns_av_sigmaI/netI    0.0941
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9325
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.55
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6343
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2013)'
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             510
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     319
_refine_ls_number_reflns         4166
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.1334
_refine_ls_R_factor_gt           0.0473
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0294P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0790
_refine_ls_wR_factor_ref         0.0996
_reflns_number_gt                2109
_reflns_number_total             4166
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            am0c08526_si_002.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Triclinic' was changed to
'triclinic' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_sg_symbol_Hall     '-P 1   '
_cod_original_sg_symbol_H-M      'P-1   '
_cod_database_code               4517824
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.9579(3) 0.8664(3) 0.9839(2) 0.0263(6) Uani 1 1 d . . .
C2 C 0.9013(3) 0.6299(3) 1.0284(2) 0.0243(6) Uani 1 1 d . . .
C3 C 0.8155(3) 0.4780(3) 1.0061(2) 0.0253(6) Uani 1 1 d . . .
C4 C 0.6625(3) 0.2482(2) 0.9070(2) 0.0317(7) Uani 1 1 d . . .
H4A H 0.6752 0.2182 0.9738 0.038 Uiso 1 1 calc R . .
H4B H 0.7150 0.2111 0.8548 0.038 Uiso 1 1 calc R . .
C5 C 0.4963(3) 0.1875(3) 0.8736(2) 0.0350(7) Uani 1 1 d . . .
C6A C 0.4955(4) 0.6980(4) 0.7020(3) 0.0745(12) Uani 1 1 d . . .
H6A H 0.4678 0.7254 0.7725 0.089 Uiso 1 1 calc R . .
C7A C 0.4263(4) 0.5386(4) 0.6810(3) 0.0840(13) Uani 1 1 d . . .
H7A1 H 0.4522 0.5076 0.6126 0.126 Uiso 1 1 calc R . .
H7A2 H 0.3165 0.5020 0.6824 0.126 Uiso 1 1 calc R . .
H7A3 H 0.4650 0.5020 0.7340 0.126 Uiso 1 1 calc R . .
C8A C 0.4404(5) 0.7630(5) 0.6300(5) 0.135(2) Uani 1 1 d . . .
H8A1 H 0.4878 0.8665 0.6496 0.202 Uiso 1 1 calc R . .
H8A2 H 0.3308 0.7279 0.6321 0.202 Uiso 1 1 calc R . .
H8A3 H 0.4656 0.7384 0.5598 0.202 Uiso 1 1 calc R . .
C6B C 0.8706(4) 0.1339(4) 0.6518(3) 0.0676(11) Uani 1 1 d . . .
H6B H 0.8891 0.2348 0.6760 0.081 Uiso 1 1 calc R . .
C7B C 0.7641(5) 0.0848(5) 0.5612(3) 0.1080(16) Uani 1 1 d . . .
H7B1 H 0.7452 -0.0132 0.5333 0.162 Uiso 1 1 calc R . .
H7B2 H 0.8065 0.1463 0.5083 0.162 Uiso 1 1 calc R . .
H7B3 H 0.6692 0.0881 0.5812 0.162 Uiso 1 1 calc R . .
C8B C 1.0230(4) 0.1340(4) 0.6356(3) 0.0845(13) Uani 1 1 d . . .
H8B1 H 1.0871 0.1757 0.7000 0.127 Uiso 1 1 calc R . .
H8B2 H 1.0700 0.1901 0.5806 0.127 Uiso 1 1 calc R . .
H8B3 H 1.0109 0.0361 0.6156 0.127 Uiso 1 1 calc R . .
C6C C 0.9054(4) 0.5982(4) 0.6830(3) 0.0536(9) Uani 1 1 d . . .
H6C H 0.9468 0.5292 0.6966 0.064 Uiso 1 1 calc R . .
C7C C 1.0346(4) 0.7412(4) 0.6949(3) 0.0951(15) Uani 1 1 d . . .
H7C1 H 0.9978 0.8129 0.6854 0.143 Uiso 1 1 calc R . .
H7C2 H 1.1065 0.7417 0.6428 0.143 Uiso 1 1 calc R . .
H7C3 H 1.0846 0.7631 0.7642 0.143 Uiso 1 1 calc R . .
C8C C 0.8262(4) 0.5474(5) 0.5771(3) 0.0886(13) Uani 1 1 d . . .
H8C1 H 0.7430 0.4532 0.5759 0.133 Uiso 1 1 calc R . .
H8C2 H 0.8975 0.5417 0.5262 0.133 Uiso 1 1 calc R . .
H8C3 H 0.7864 0.6142 0.5599 0.133 Uiso 1 1 calc R . .
N1 N 0.9757(2) 1.0661(2) 0.92278(18) 0.0318(6) Uani 1 1 d . . .
N2 N 0.9321(2) 0.9266(2) 0.90550(18) 0.0315(6) Uani 1 1 d . . .
N3 N 0.9083(2) 0.7216(2) 0.96070(18) 0.0270(6) Uani 1 1 d D . .
H3 H 0.874(3) 0.683(3) 0.8992(14) 0.032 Uiso 1 1 d D . .
N4 N 0.9674(2) 0.6652(2) 1.12065(18) 0.0330(6) Uani 1 1 d . . .
N5 N 0.8296(2) 0.4216(2) 1.08585(19) 0.0354(6) Uani 1 1 d . . .
N6 N 0.7287(2) 0.4027(2) 0.91814(19) 0.0299(6) Uani 1 1 d D . .
H6 H 0.748(3) 0.438(3) 0.8647(16) 0.036 Uiso 1 1 d D . .
N7 N 0.4227(3) 0.2774(3) 0.9278(3) 0.0455(7) Uani 1 1 d . . .
N8 N 0.4103(3) 0.0376(3) 0.8989(2) 0.0467(7) Uani 1 1 d . . .
N9 N 0.4672(3) 0.1766(3) 0.7578(2) 0.0488(7) Uani 1 1 d . . .
O1 O 0.92336(19) 0.53570(19) 1.15987(15) 0.0395(5) Uani 1 1 d . . .
O2 O 0.4383(2) 0.2957(2) 1.0219(2) 0.0591(7) Uani 1 1 d . . .
O3 O 0.3580(2) 0.3235(2) 0.8738(2) 0.0686(8) Uani 1 1 d . . .
O4 O 0.4785(2) -0.0364(2) 0.88518(18) 0.0560(6) Uani 1 1 d . . .
O5 O 0.2857(2) 0.0044(2) 0.9305(2) 0.0677(8) Uani 1 1 d . . .
O6 O 0.5626(2) 0.2675(2) 0.71651(17) 0.0597(7) Uani 1 1 d . . .
O7 O 0.3525(3) 0.0803(3) 0.7161(2) 0.0835(9) Uani 1 1 d . . .
O8A O 0.6536(2) 0.7469(2) 0.7068(2) 0.0602(7) Uani 1 1 d D . .
H8A H 0.696(3) 0.8329(19) 0.721(3) 0.072 Uiso 1 1 d D . .
O8B O 0.8003(2) 0.0550(2) 0.73314(17) 0.0458(6) Uani 1 1 d D . .
H8B H 0.865(3) 0.086(3) 0.7806(19) 0.055 Uiso 1 1 d D . .
O8C O 0.8002(2) 0.5945(2) 0.76028(16) 0.0387(5) Uani 1 1 d D . .
H8C H 0.754(3) 0.640(3) 0.748(2) 0.046 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
N1 C1 N2 126.3(2) 2_777 . ?
N1 C1 N3 120.2(2) 2_777 . ?
N2 C1 N3 113.6(2) . . ?
N4 C2 N3 126.0(2) . . ?
N4 C2 C3 110.3(2) . . ?
N3 C2 C3 123.7(2) . . ?
N5 C3 N6 124.1(2) . . ?
N5 C3 C2 108.8(2) . . ?
N6 C3 C2 127.1(2) . . ?
N6 C4 C5 110.2(2) . . ?
N6 C4 H4A 109.6 . . ?
C5 C4 H4A 109.6 . . ?
N6 C4 H4B 109.6 . . ?
C5 C4 H4B 109.6 . . ?
H4A C4 H4B 108.1 . . ?
C4 C5 N9 113.0(2) . . ?
C4 C5 N7 111.2(2) . . ?
N9 C5 N7 107.7(2) . . ?
C4 C5 N8 112.1(2) . . ?
N9 C5 N8 105.7(2) . . ?
N7 C5 N8 106.8(2) . . ?
O8A C6A C8A 113.2(3) . . ?
O8A C6A C7A 108.1(3) . . ?
C8A C6A C7A 113.9(3) . . ?
O8A C6A H6A 107.1 . . ?
C8A C6A H6A 107.1 . . ?
C7A C6A H6A 107.1 . . ?
C6A C7A H7A1 109.5 . . ?
C6A C7A H7A2 109.5 . . ?
H7A1 C7A H7A2 109.5 . . ?
C6A C7A H7A3 109.5 . . ?
H7A1 C7A H7A3 109.5 . . ?
H7A2 C7A H7A3 109.5 . . ?
C6A C8A H8A1 109.5 . . ?
C6A C8A H8A2 109.5 . . ?
H8A1 C8A H8A2 109.5 . . ?
C6A C8A H8A3 109.5 . . ?
H8A1 C8A H8A3 109.5 . . ?
H8A2 C8A H8A3 109.5 . . ?
O8B C6B C7B 109.0(3) . . ?
O8B C6B C8B 110.8(3) . . ?
C7B C6B C8B 116.7(4) . . ?
O8B C6B H6B 106.6 . . ?
C7B C6B H6B 106.6 . . ?
C8B C6B H6B 106.6 . . ?
C6B C7B H7B1 109.5 . . ?
C6B C7B H7B2 109.5 . . ?
H7B1 C7B H7B2 109.5 . . ?
C6B C7B H7B3 109.5 . . ?
H7B1 C7B H7B3 109.5 . . ?
H7B2 C7B H7B3 109.5 . . ?
C6B C8B H8B1 109.5 . . ?
C6B C8B H8B2 109.5 . . ?
H8B1 C8B H8B2 109.5 . . ?
C6B C8B H8B3 109.5 . . ?
H8B1 C8B H8B3 109.5 . . ?
H8B2 C8B H8B3 109.5 . . ?
O8C C6C C7C 110.3(3) . . ?
O8C C6C C8C 110.6(3) . . ?
C7C C6C C8C 114.7(3) . . ?
O8C C6C H6C 107.0 . . ?
C7C C6C H6C 107.0 . . ?
C8C C6C H6C 107.0 . . ?
C6C C7C H7C1 109.5 . . ?
C6C C7C H7C2 109.5 . . ?
H7C1 C7C H7C2 109.5 . . ?
C6C C7C H7C3 109.5 . . ?
H7C1 C7C H7C3 109.5 . . ?
H7C2 C7C H7C3 109.5 . . ?
C6C C8C H8C1 109.5 . . ?
C6C C8C H8C2 109.5 . . ?
H8C1 C8C H8C2 109.5 . . ?
C6C C8C H8C3 109.5 . . ?
H8C1 C8C H8C3 109.5 . . ?
H8C2 C8C H8C3 109.5 . . ?
N2 N1 C1 116.9(2) . 2_777 ?
N1 N2 C1 116.8(2) . . ?
C2 N3 C1 126.7(2) . . ?
C2 N3 H3 115.5(18) . . ?
C1 N3 H3 117.8(18) . . ?
C2 N4 O1 104.7(2) . . ?
C3 N5 O1 105.7(2) . . ?
C3 N6 C4 118.3(2) . . ?
C3 N6 H6 118.1(19) . . ?
C4 N6 H6 117(2) . . ?
O3 N7 O2 127.9(3) . . ?
O3 N7 C5 117.4(3) . . ?
O2 N7 C5 114.7(3) . . ?
O5 N8 O4 127.0(3) . . ?
O5 N8 C5 118.8(2) . . ?
O4 N8 C5 114.2(2) . . ?
O6 N9 O7 126.6(3) . . ?
O6 N9 C5 115.3(2) . . ?
O7 N9 C5 118.0(3) . . ?
N5 O1 N4 110.47(18) . . ?
C6A O8A H8A 112(2) . . ?
C6B O8B H8B 104(2) . . ?
C6C O8C H8C 111(2) . . ?
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
C1 N1 1.338(3) 2_777 ?
C1 N2 1.346(3) . ?
C1 N3 1.374(3) . ?
C2 N4 1.297(3) . ?
C2 N3 1.371(3) . ?
C2 C3 1.441(3) . ?
C3 N5 1.297(3) . ?
C3 N6 1.361(3) . ?
C4 N6 1.455(3) . ?
C4 C5 1.516(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 N9 1.518(4) . ?
C5 N7 1.518(4) . ?
C5 N8 1.521(3) . ?
C6A O8A 1.410(4) . ?
C6A C8A 1.453(5) . ?
C6A C7A 1.501(4) . ?
C6A H6A 1.0000 . ?
C7A H7A1 0.9800 . ?
C7A H7A2 0.9800 . ?
C7A H7A3 0.9800 . ?
C8A H8A1 0.9800 . ?
C8A H8A2 0.9800 . ?
C8A H8A3 0.9800 . ?
C6B O8B 1.430(4) . ?
C6B C7B 1.460(5) . ?
C6B C8B 1.508(4) . ?
C6B H6B 1.0000 . ?
C7B H7B1 0.9800 . ?
C7B H7B2 0.9800 . ?
C7B H7B3 0.9800 . ?
C8B H8B1 0.9800 . ?
C8B H8B2 0.9800 . ?
C8B H8B3 0.9800 . ?
C6C O8C 1.438(4) . ?
C6C C7C 1.489(4) . ?
C6C C8C 1.499(4) . ?
C6C H6C 1.0000 . ?
C7C H7C1 0.9800 . ?
C7C H7C2 0.9800 . ?
C7C H7C3 0.9800 . ?
C8C H8C1 0.9800 . ?
C8C H8C2 0.9800 . ?
C8C H8C3 0.9800 . ?
N1 N2 1.325(3) . ?
N1 C1 1.338(3) 2_777 ?
N3 H3 0.848(16) . ?
N4 O1 1.408(2) . ?
N5 O1 1.404(3) . ?
N6 H6 0.820(16) . ?
N7 O3 1.215(3) . ?
N7 O2 1.217(3) . ?
N8 O5 1.211(3) . ?
N8 O4 1.216(3) . ?
N9 O6 1.209(3) . ?
N9 O7 1.215(3) . ?
O8A H8A 0.812(18) . ?
O8B H8B 0.814(17) . ?
O8C H8C 0.812(16) . ?
