#------------------------------------------------------------------------------
#$Date: 2020-07-02 00:15:54 +0300 (Thu, 02 Jul 2020) $
#$Revision: 253625 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/78/4517825.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_4517825
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         'C6 H2 N14 O6, 4(C2 H6 O S), 2(H4 N)'
_chemical_formula_sum            'C14 H34 N16 O10 S4'
_chemical_formula_weight         714.81
_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   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                106.6420(10)
_cell_angle_beta                 100.4740(10)
_cell_angle_gamma                111.1800(10)
_cell_formula_units_Z            1
_cell_length_a                   7.6145(3)
_cell_length_b                   10.1856(4)
_cell_length_c                   12.0493(5)
_cell_measurement_reflns_used    2240
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.247
_cell_measurement_theta_min      2.897
_cell_volume                     791.19(6)
_computing_cell_refinement       'Bruker APEX3 v2015.5-2 (Bruker, 2015)'
_computing_data_collection       'Bruker APEX3 v2015.5-2 (Bruker, 2015)'
_computing_data_reduction
;
Bruker SAINT v8.34A (Bruker, 2013), Bruker XPREP v2014/2 (Bruker, 2014)
;
_computing_molecular_graphics    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_publication_material  'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_av_unetI/netI     0.0408
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.944
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9517
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.010
_diffrn_reflns_theta_min         3.027
_exptl_absorpt_coefficient_mu    0.373
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.7004
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2014/5 (Bruker, 2008)'
_exptl_crystal_colour            'clear red'
_exptl_crystal_density_diffrn    1.500
_exptl_crystal_description       plate
_exptl_crystal_F_000             374
_exptl_crystal_size_max          0.345
_exptl_crystal_size_mid          0.285
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         4369
_refine_ls_number_restraints     17
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0876
_refine_ls_R_factor_gt           0.0469
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0640P)²+0.1137P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1121
_refine_ls_wR_factor_ref         0.1327
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2770
_reflns_number_total             4369
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            am0c08526_si_005.cif
_cod_data_source_block           shrv650
_cod_database_code               4517825
_shelx_shelxl_version_number     2014/7
_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_min   0.882
_shelx_estimated_absorpt_t_max   0.985
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
O1 O 0.7211(3) 0.65722(19) 0.57689(16) 0.0614(5) Uani 1 1 d . . . . .
O2 O 0.8961(3) 0.8730(2) 0.72826(19) 0.0897(7) Uani 1 1 d . . . . .
N3 N 0.7426(3) 0.7868(2) 0.64127(16) 0.0448(4) Uani 1 1 d . . . . .
N4 N 0.5986(3) 0.82454(19) 0.60858(15) 0.0418(4) Uani 1 1 d . . . . .
C5 C 0.6217(3) 0.9643(2) 0.68219(17) 0.0371(4) Uani 1 1 d . . . . .
N6 N 0.7642(3) 1.0724(2) 0.78086(17) 0.0522(5) Uani 1 1 d . . . . .
O7 O 0.7022(3) 1.18780(18) 0.81445(15) 0.0605(5) Uani 1 1 d . . . . .
N8 N 0.5177(3) 1.1477(2) 0.73316(16) 0.0483(4) Uani 1 1 d . . . . .
C9 C 0.4686(3) 1.0129(2) 0.65410(17) 0.0356(4) Uani 1 1 d . . . . .
N10 N 0.2947(2) 0.92656(18) 0.55680(15) 0.0370(4) Uani 1 1 d . . . . .
H10 H 0.2796 0.8396 0.5090 0.044 Uiso 1 1 calc R U . . .
C11 C 0.1443(3) 0.9670(2) 0.52948(17) 0.0339(4) Uani 1 1 d . . . . .
N12 N 0.1706(3) 1.10872(19) 0.58929(17) 0.0446(4) Uani 1 1 d . . . . .
N13 N 0.0217(3) 1.14289(19) 0.55916(17) 0.0464(4) Uani 1 1 d . . . . .
O14 O 0.4418(3) 0.3424(2) 1.13396(15) 0.0776(6) Uani 1 1 d D . . . .
S15A S 0.25254(10) 0.23028(8) 1.03208(5) 0.0564(3) Uani 0.920(2) 1 d D . P A 1
C16A C 0.2794(5) 0.0641(3) 0.9730(3) 0.0741(7) Uani 0.920(2) 1 d D . P A 1
H16A H 0.4035 0.0886 0.9565 0.111 Uiso 0.920(2) 1 calc R U P A 1
H16B H 0.1721 -0.0045 0.8986 0.111 Uiso 0.920(2) 1 calc R U P A 1
H16C H 0.2774 0.0166 1.0313 0.111 Uiso 0.920(2) 1 calc R U P A 1
C17A C 0.2661(6) 0.2918(4) 0.9101(3) 0.0741(7) Uani 0.920(2) 1 d D . P A 1
H17A H 0.2656 0.3900 0.9323 0.111 Uiso 0.920(2) 1 calc R U P A 1
H17B H 0.1538 0.2199 0.8392 0.111 Uiso 0.920(2) 1 calc R U P A 1
H17C H 0.3864 0.2990 0.8923 0.111 Uiso 0.920(2) 1 calc R U P A 1
S15B S 0.4070(16) 0.2556(11) 1.0063(7) 0.088(4) Uani 0.080(2) 1 d D . P A 2
C16B C 0.343(6) 0.0619(14) 0.963(3) 0.0741(7) Uani 0.080(2) 1 d D . P A 2
H16D H 0.3643 0.0389 1.0350 0.111 Uiso 0.080(2) 1 calc R U P A 2
H16E H 0.4235 0.0359 0.9167 0.111 Uiso 0.080(2) 1 calc R U P A 2
H16F H 0.2053 0.0042 0.9145 0.111 Uiso 0.080(2) 1 calc R U P A 2
C17B C 0.233(5) 0.248(3) 0.883(2) 0.0741(7) Uani 0.080(2) 1 d D . P A 2
H17D H 0.1022 0.1772 0.8743 0.111 Uiso 0.080(2) 1 calc R U P A 2
H17E H 0.2642 0.2149 0.8095 0.111 Uiso 0.080(2) 1 calc R U P A 2
H17F H 0.2383 0.3473 0.8990 0.111 Uiso 0.080(2) 1 calc R U P A 2
O18 O 1.1513(2) 0.62195(17) 0.37350(14) 0.0501(4) Uani 1 1 d . . . . .
S19 S 0.93860(8) 0.53053(6) 0.28924(5) 0.04400(17) Uani 1 1 d . . . . .
C20 C 0.8280(4) 0.3823(4) 0.3385(3) 0.0800(9) Uani 1 1 d . . . . .
H20A H 0.9126 0.3329 0.3479 0.120 Uiso 1 1 calc R U . . .
H20B H 0.7014 0.3095 0.2790 0.120 Uiso 1 1 calc R U . . .
H20C H 0.8099 0.4240 0.4155 0.120 Uiso 1 1 calc R U . . .
C21 C 0.9529(5) 0.4175(4) 0.1520(3) 0.0841(10) Uani 1 1 d . . . . .
H21A H 1.0347 0.4826 0.1194 0.126 Uiso 1 1 calc R U . . .
H21B H 0.8220 0.3564 0.0937 0.126 Uiso 1 1 calc R U . . .
H21C H 1.0099 0.3523 0.1686 0.126 Uiso 1 1 calc R U . . .
N22 N 0.4827(3) 0.5846(2) 0.33897(16) 0.0421(4) Uani 1 1 d D . . . .
H22A H 0.547(3) 0.6707(19) 0.3269(19) 0.063 Uiso 1 1 d D U . . .
H22B H 0.467(4) 0.5034(19) 0.2761(19) 0.063 Uiso 1 1 d D U . . .
H22C H 0.552(3) 0.593(3) 0.4134(17) 0.063 Uiso 1 1 d D U . . .
H22D H 0.361(2) 0.580(3) 0.344(2) 0.063 Uiso 1 1 d D U . . .
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'
S S 0.1246 0.1234 '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
O2 N3 O1 119.64(19) . . ?
O2 N3 N4 123.37(19) . . ?
O1 N3 N4 116.96(17) . . ?
N3 N4 C5 116.11(17) . . ?
N6 C5 N4 132.2(2) . . ?
N6 C5 C9 108.29(18) . . ?
N4 C5 C9 119.55(17) . . ?
C5 N6 O7 105.31(18) . . ?
N8 O7 N6 111.21(15) . . ?
C9 N8 O7 104.72(17) . . ?
N8 C9 N10 125.25(18) . . ?
N8 C9 C5 110.47(18) . . ?
N10 C9 C5 124.28(17) . . ?
C11 N10 C9 125.87(16) . . ?
C11 N10 H10 117.1 . . ?
C9 N10 H10 117.1 . . ?
N12 C11 N13 124.79(18) . 2_576 ?
N12 C11 N10 119.80(17) . . ?
N13 C11 N10 115.41(16) 2_576 . ?
N13 N12 C11 117.67(17) . . ?
N12 N13 C11 117.54(16) . 2_576 ?
O14 S15A C16A 106.62(15) . . ?
O14 S15A C17A 105.05(15) . . ?
C16A S15A C17A 99.27(16) . . ?
S15A C16A H16A 109.5 . . ?
S15A C16A H16B 109.5 . . ?
H16A C16A H16B 109.5 . . ?
S15A C16A H16C 109.5 . . ?
H16A C16A H16C 109.5 . . ?
H16B C16A H16C 109.5 . . ?
S15A C17A H17A 109.5 . . ?
S15A C17A H17B 109.5 . . ?
H17A C17A H17B 109.5 . . ?
S15A C17A H17C 109.5 . . ?
H17A C17A H17C 109.5 . . ?
H17B C17A H17C 109.5 . . ?
O14 S15B C16B 117.3(14) . . ?
O14 S15B C17B 123.6(13) . . ?
C16B S15B C17B 99.3(2) . . ?
S15B C16B H16D 109.5 . . ?
S15B C16B H16E 109.5 . . ?
H16D C16B H16E 109.5 . . ?
S15B C16B H16F 109.5 . . ?
H16D C16B H16F 109.5 . . ?
H16E C16B H16F 109.5 . . ?
S15B C17B H17D 109.5 . . ?
S15B C17B H17E 109.5 . . ?
H17D C17B H17E 109.5 . . ?
S15B C17B H17F 109.5 . . ?
H17D C17B H17F 109.5 . . ?
H17E C17B H17F 109.5 . . ?
O18 S19 C20 106.04(11) . . ?
O18 S19 C21 105.01(13) . . ?
C20 S19 C21 97.55(17) . . ?
S19 C20 H20A 109.5 . . ?
S19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
S19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
S19 C21 H21A 109.5 . . ?
S19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
S19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
H22A N22 H22B 109.3(17) . . ?
H22A N22 H22C 108.6(17) . . ?
H22B N22 H22C 114(2) . . ?
H22A N22 H22D 106.9(17) . . ?
H22B N22 H22D 111(2) . . ?
H22C N22 H22D 107.2(17) . . ?
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
O1 N3 1.258(2) . ?
O2 N3 1.233(2) . ?
N3 N4 1.319(2) . ?
N4 C5 1.372(3) . ?
C5 N6 1.312(3) . ?
C5 C9 1.445(3) . ?
N6 O7 1.402(3) . ?
O7 N8 1.398(2) . ?
N8 C9 1.297(2) . ?
C9 N10 1.380(2) . ?
N10 C11 1.368(2) . ?
N10 H10 0.8600 . ?
C11 N12 1.337(2) . ?
C11 N13 1.339(2) 2_576 ?
N12 N13 1.321(2) . ?
N13 C11 1.339(2) 2_576 ?
O14 S15B 1.457(7) . ?
O14 S15A 1.5007(18) . ?
S15A C16A 1.739(3) . ?
S15A C17A 1.760(3) . ?
C16A H16A 0.9600 . ?
C16A H16B 0.9600 . ?
C16A H16C 0.9600 . ?
C17A H17A 0.9600 . ?
C17A H17B 0.9600 . ?
C17A H17C 0.9600 . ?
S15B C16B 1.739(3) . ?
S15B C17B 1.760(3) . ?
C16B H16D 0.9600 . ?
C16B H16E 0.9600 . ?
C16B H16F 0.9600 . ?
C17B H17D 0.9600 . ?
C17B H17E 0.9600 . ?
C17B H17F 0.9600 . ?
O18 S19 1.5138(15) . ?
S19 C20 1.766(3) . ?
S19 C21 1.771(3) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
N22 H22A 0.904(13) . ?
N22 H22B 0.901(15) . ?
N22 H22C 0.917(14) . ?
N22 H22D 0.927(15) . ?
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
N10 H10 O18 0.86 2.08 2.906(2) 161.6 1_455
C16A H16B O2 0.96 2.29 3.238(4) 167.8 1_445
C17B H17D N6 0.96 2.30 3.16(3) 148.4 1_445
N22 H22A N8 0.904(13) 2.342(18) 3.091(3) 140.2(19) 2_676
N22 H22A N12 0.904(13) 2.262(17) 3.023(2) 141.6(18) 2_676
N22 H22B O14 0.901(15) 1.923(16) 2.821(2) 175(2) 1_554
N22 H22C O1 0.917(14) 1.923(16) 2.826(2) 168(2) .
N22 H22D O18 0.927(15) 1.860(16) 2.769(2) 166(2) 1_455
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 N3 N4 C5 -4.1(3) . . . . ?
O1 N3 N4 C5 177.95(18) . . . . ?
N3 N4 C5 N6 1.1(3) . . . . ?
N3 N4 C5 C9 -178.75(17) . . . . ?
N4 C5 N6 O7 180.0(2) . . . . ?
C9 C5 N6 O7 -0.1(2) . . . . ?
C5 N6 O7 N8 -0.3(2) . . . . ?
N6 O7 N8 C9 0.6(2) . . . . ?
O7 N8 C9 N10 179.09(17) . . . . ?
O7 N8 C9 C5 -0.6(2) . . . . ?
N6 C5 C9 N8 0.5(2) . . . . ?
N4 C5 C9 N8 -179.57(18) . . . . ?
N6 C5 C9 N10 -179.21(18) . . . . ?
N4 C5 C9 N10 0.7(3) . . . . ?
N8 C9 N10 C11 -1.7(3) . . . . ?
C5 C9 N10 C11 178.02(18) . . . . ?
C9 N10 C11 N12 9.5(3) . . . . ?
C9 N10 C11 N13 -171.23(17) . . . 2_576 ?
N13 C11 N12 N13 0.3(3) 2_576 . . . ?
N10 C11 N12 N13 179.49(18) . . . . ?
C11 N12 N13 C11 -0.3(3) . . . 2_576 ?
