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#$Date: 2023-03-24 10:09:27 +0200 (Fri, 24 Mar 2023) $
#$Revision: 282035 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/69/8106973.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_8106973
loop_
_publ_author_name
'Zhu, Jiaping'
'Jin, Shaohua'
'Yu, Yuehai'
'Chen, Shusen'
'Shu, Qinghai'
_publ_section_title
;
 Crystal structure of
 (E)-4,4′-(diazene-1,2-diyl)bis(1-nitro-1H-1,2,4-triazol-5(4H)-one)---acetonitrile
 (1:1), C6H5N11O6
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              677
_journal_page_last               678
_journal_paper_doi               10.1515/ncrs-2015-0126
_journal_volume                  231
_journal_year                    2016
_chemical_formula_sum            'C6 H5 N11 O6'
_chemical_formula_weight         327.21
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 95.961(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.463(5)
_cell_length_b                   6.526(2)
_cell_length_c                   14.068(5)
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      29.14
_cell_measurement_theta_min      2.91
_cell_volume                     1229.3(7)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      153(2)
_diffrn_detector_area_resol_mean 0
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       'phi and omega 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  0.0259
_diffrn_reflns_av_sigmaI/netI    0.0274
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10459
_diffrn_reflns_theta_full        29.14
_diffrn_reflns_theta_max         29.14
_diffrn_reflns_theta_min         2.91
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.157
_exptl_absorpt_correction_T_max  0.9799
_exptl_absorpt_correction_T_min  0.9398
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.768
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3293
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.103
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0420
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0441P)²+0.3741P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0985
_refine_ls_wR_factor_ref         0.1041
_reflns_number_gt                2888
_reflns_number_total             3293
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_ncrs-2015-0126_suppl.cif
_cod_data_source_block           bo3340
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               8106973
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.23788(9) 0.46894(18) 0.38807(9) 0.0227(3) Uani 1 1 d . A 1
N2 N 0.22069(8) 0.25935(17) 0.38915(9) 0.0217(2) Uani 1 1 d . A 1
N3 N 0.09904(8) 0.39448(17) 0.45244(8) 0.0190(2) Uani 1 1 d . A 1
N4 N 0.00861(8) 0.40903(18) 0.48960(8) 0.0200(2) Uani 1 1 d . . 1
N5 N 0.28290(8) 0.12872(18) 0.34337(8) 0.0203(2) Uani 1 1 d . A 1
O1 O 0.09524(8) 0.03671(16) 0.43527(8) 0.0294(3) Uani 1 1 d . A 1
O2 O 0.25943(8) -0.05086(16) 0.34071(8) 0.0285(2) Uani 1 1 d . A 1
O3 O 0.35370(7) 0.20830(16) 0.31165(7) 0.0259(2) Uani 1 1 d . A 1
C1 C 0.16342(10) 0.5450(2) 0.42664(10) 0.0218(3) Uani 1 1 d . A 1
H1 H 0.1539 0.6875 0.4362 0.026 Uiso 1 1 calc R A 1
C2 C 0.13203(10) 0.2013(2) 0.42649(10) 0.0200(3) Uani 1 1 d . A 1
N6 N 0.47219(9) 0.79243(18) 0.27212(8) 0.0227(3) Uani 1 1 d . B 1
N7 N 0.53374(9) 0.93320(18) 0.32263(8) 0.0226(3) Uani 1 1 d . B 1
N8 N 0.51346(9) 0.69205(18) 0.42116(8) 0.0213(2) Uani 1 1 d . B 1
N9 N 0.52388(9) 0.58194(18) 0.50493(8) 0.0230(3) Uani 1 1 d . . 1
N10 N 0.55065(9) 1.12346(18) 0.28035(9) 0.0229(3) Uani 1 1 d . B 1
O4 O 0.61266(9) 0.96900(17) 0.48011(8) 0.0325(3) Uani 1 1 d . B 1
O5 O 0.59153(8) 1.25157(17) 0.33330(8) 0.0310(3) Uani 1 1 d . B 1
O6 O 0.52377(9) 1.13875(18) 0.19603(8) 0.0336(3) Uani 1 1 d . B 1
C3 C 0.46157(10) 0.6493(2) 0.33340(10) 0.0221(3) Uani 1 1 d . B 1
H3 H 0.4228 0.5292 0.3199 0.027 Uiso 1 1 calc R B 1
C4 C 0.56134(10) 0.8811(2) 0.41830(10) 0.0226(3) Uani 1 1 d . B 1
N11 N 0.76097(13) 0.1330(3) 0.16577(12) 0.0471(4) Uani 1 1 d . . .
C5 C 0.79274(13) 0.1223(3) 0.24436(13) 0.0351(4) Uani 1 1 d . . .
C6 C 0.83270(14) 0.1103(3) 0.34411(13) 0.0413(4) Uani 1 1 d . . .
H6A H 0.8919 0.0218 0.3503 0.050 Uiso 1 1 calc R . .
H6B H 0.7820 0.0530 0.3817 0.050 Uiso 1 1 calc R . .
H6C H 0.8512 0.2478 0.3677 0.050 Uiso 1 1 calc R . .
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
C1 N1 N2 103.74(11) . .
N1 N2 N5 119.17(11) . .
N1 N2 C2 114.77(11) . .
N5 N2 C2 125.49(11) . .
N4 N3 C1 130.79(11) . .
N4 N3 C2 118.60(11) . .
C1 N3 C2 110.32(11) . .
N4 N4 N3 110.31(13) 3_566 .
O3 N5 O2 127.99(12) . .
O3 N5 N2 116.13(11) . .
O2 N5 N2 115.89(11) . .
N1 C1 N3 111.90(12) . .
N1 C1 H1 124.1 . .
N3 C1 H1 124.1 . .
O1 C2 N3 129.61(13) . .
O1 C2 N2 131.18(13) . .
N3 C2 N2 99.20(11) . .
C3 N6 N7 103.87(11) . .
N6 N7 C4 114.69(11) . .
N6 N7 N10 118.95(11) . .
C4 N7 N10 125.63(11) . .
N9 N8 C3 131.08(12) . .
N9 N8 C4 118.74(11) . .
C3 N8 C4 110.17(11) . .
N9 N9 N8 110.31(14) 3_666 .
O6 N10 O5 128.07(13) . .
O6 N10 N7 116.33(12) . .
O5 N10 N7 115.60(12) . .
N6 C3 N8 111.74(12) . .
N6 C3 H3 124.1 . .
N8 C3 H3 124.1 . .
O4 C4 N8 129.45(13) . .
O4 C4 N7 131.03(13) . .
N8 C4 N7 99.50(11) . .
N11 C5 C6 179.6(2) . .
C5 C6 H6A 109.5 . .
C5 C6 H6B 109.5 . .
H6A C6 H6B 109.5 . .
C5 C6 H6C 109.5 . .
H6A C6 H6C 109.5 . .
H6B C6 H6C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C1 1.2880(18) .
N1 N2 1.3876(16) .
N2 N5 1.3982(16) .
N2 C2 1.4052(17) .
N3 N4 1.3771(15) .
N3 C1 1.3834(18) .
N3 C2 1.3977(18) .
N4 N4 1.250(2) 3_566
N5 O3 1.2106(15) .
N5 O2 1.2134(15) .
O1 C2 1.1945(17) .
C1 H1 0.9500 .
N6 C3 1.2890(18) .
N6 N7 1.3832(16) .
N7 C4 1.4003(18) .
N7 N10 1.4055(17) .
N8 N9 1.3749(16) .
N8 C3 1.3824(17) .
N8 C4 1.3947(18) .
N9 N9 1.248(2) 3_666
N10 O6 1.2078(16) .
N10 O5 1.2131(16) .
O4 C4 1.1989(17) .
C3 H3 0.9500 .
N11 C5 1.145(2) .
C5 C6 1.452(2) .
C6 H6A 0.9800 .
C6 H6B 0.9800 .
C6 H6C 0.9800 .
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
C1 N1 N2 N5 173.67(12) . . . .
C1 N1 N2 C2 1.86(16) . . . .
C1 N3 N4 N4 -7.9(2) . . . 3_566
C2 N3 N4 N4 178.84(13) . . . 3_566
N1 N2 N5 O3 5.65(17) . . . .
C2 N2 N5 O3 176.50(12) . . . .
N1 N2 N5 O2 -174.67(12) . . . .
C2 N2 N5 O2 -3.81(19) . . . .
N2 N1 C1 N3 -0.05(15) . . . .
N4 N3 C1 N1 -175.42(13) . . . .
C2 N3 C1 N1 -1.72(16) . . . .
N4 N3 C2 O1 -3.8(2) . . . .
C1 N3 C2 O1 -178.34(15) . . . .
N4 N3 C2 N2 177.10(11) . . . .
C1 N3 C2 N2 2.53(14) . . . .
N1 N2 C2 O1 178.17(15) . . . .
N5 N2 C2 O1 7.0(2) . . . .
N1 N2 C2 N3 -2.72(15) . . . .
N5 N2 C2 N3 -173.93(12) . . . .
C3 N6 N7 C4 -1.21(16) . . . .
C3 N6 N7 N10 -171.96(12) . . . .
C3 N8 N9 N9 -0.4(2) . . . 3_666
C4 N8 N9 N9 179.72(14) . . . 3_666
N6 N7 N10 O6 -12.16(18) . . . .
C4 N7 N10 O6 178.20(13) . . . .
N6 N7 N10 O5 168.54(12) . . . .
C4 N7 N10 O5 -1.1(2) . . . .
N7 N6 C3 N8 0.11(15) . . . .
N9 N8 C3 N6 -178.90(13) . . . .
C4 N8 C3 N6 1.00(17) . . . .
N9 N8 C4 O4 -0.3(2) . . . .
C3 N8 C4 O4 179.82(16) . . . .
N9 N8 C4 N7 178.36(11) . . . .
C3 N8 C4 N7 -1.55(14) . . . .
N6 N7 C4 O4 -179.69(16) . . . .
N10 N7 C4 O4 -9.7(3) . . . .
N6 N7 C4 N8 1.71(15) . . . .
N10 N7 C4 N8 171.74(12) . . . .
