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#$Date: 2025-08-18 18:02:58 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301777 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/52/01/1520154.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_1520154
loop_
_publ_author_name
'Coles, Simon J.'
'Hursthouse, Michael B.'
'Sengul, Abdurrahaman'
_publ_section_title
;
 Ag(I)-1,2-bis((N-methyl-imidazol-2-yl)methylene)hydrazine triflate
;
_journal_name_full               'Crystal Structure Report Archive'
_journal_page_first              520
_journal_year                    2008
_chemical_formula_sum            'C11 H12 Ag F3 N6 O3 S'
_chemical_formula_weight         473.20
_space_group_IT_number           2
_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
_cell_angle_alpha                96.4450(10)
_cell_angle_beta                 111.7310(10)
_cell_angle_gamma                97.3180(10)
_cell_formula_units_Z            4
_cell_length_a                   10.95900(10)
_cell_length_b                   11.4830(2)
_cell_length_c                   14.0360(2)
_cell_measurement_reflns_used    52416
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     1602.88(4)
_computing_cell_refinement       'DENZO, COLLECT'
_computing_data_reduction        'DENZO, COLLECT'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR2004 (Giacovazzo, 2004)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD Area Detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0488
_diffrn_reflns_av_sigmaI/netI    0.0395
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            35959
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         3.17
_exptl_absorpt_coefficient_mu    1.446
_exptl_absorpt_correction_T_max  0.891
_exptl_absorpt_correction_T_min  0.862
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2.10 (Sheldrick, G.M., 2003)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.961
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.735
_refine_diff_density_min         -0.874
_refine_diff_density_rms         0.111
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     451
_refine_ls_number_reflns         7338
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0352
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0362P)²+2.6361P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0832
_refine_ls_wR_factor_ref         0.0878
_reflns_number_gt                6364
_reflns_number_total             7338
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            eCrystal-520.cif
_cod_data_source_block           2008sjc0013
_cod_depositor_comments
;
Citation :
Coles, Simon J. and Hursthouse, Michael B. and Sengul, Abdurrahaman (2008) 
University of Southampton, Crystal Structure Report Archive. 
(doi:10.5258/ecrystals/520)

More at:
http://ecrystals.chem.soton.ac.uk/520/

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 3392 2015-05-12 13:50:21Z andrius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1520154
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 0.8636(3) 0.5369(3) 0.9113(2) 0.0178(6) Uani 1 1 d . . .
C2 C 0.7475(3) 0.3416(3) 0.9320(3) 0.0284(7) Uani 1 1 d . . .
H2A H 0.7419 0.2575 0.9059 0.043 Uiso 1 1 calc R . .
H2B H 0.6577 0.3612 0.9076 0.043 Uiso 1 1 calc R . .
H2C H 0.7869 0.3563 1.0083 0.043 Uiso 1 1 calc R . .
C3 C 0.8919(3) 0.3742(3) 0.8306(2) 0.0212(6) Uani 1 1 d . . .
H3 H 0.8878 0.2932 0.8047 0.025 Uiso 1 1 calc R . .
C4 C 0.9604(3) 0.4732(3) 0.8128(2) 0.0210(6) Uani 1 1 d . . .
H4 H 1.0125 0.4714 0.7718 0.025 Uiso 1 1 calc R . .
C5 C 0.8173(3) 0.6173(3) 0.9722(2) 0.0181(6) Uani 1 1 d . . .
H5 H 0.7619 0.5875 1.0058 0.022 Uiso 1 1 calc R . .
C6 C 0.8400(3) 0.9103(3) 1.0491(2) 0.0175(6) Uani 1 1 d . . .
H6 H 0.9088 0.9366 1.0264 0.021 Uiso 1 1 calc R . .
C7 C 0.7889(3) 0.9975(3) 1.0990(2) 0.0169(6) Uani 1 1 d . . .
C8 C 0.5827(3) 0.8659(3) 1.0968(3) 0.0268(7) Uani 1 1 d . . .
H8A H 0.5115 0.8793 1.1208 0.040 Uiso 1 1 calc R . .
H8B H 0.6300 0.8065 1.1326 0.040 Uiso 1 1 calc R . .
H8C H 0.5438 0.8369 1.0215 0.040 Uiso 1 1 calc R . .
C9 C 0.6624(3) 1.0857(3) 1.1628(2) 0.0207(6) Uani 1 1 d . . .
H9 H 0.5931 1.1001 1.1854 0.025 Uiso 1 1 calc R . .
C10 C 0.7661(3) 1.1684(3) 1.1669(2) 0.0195(6) Uani 1 1 d . . .
H10 H 0.7814 1.2512 1.1931 0.023 Uiso 1 1 calc R . .
C11 C 0.2364(3) 0.5180(3) 0.4259(2) 0.0186(6) Uani 1 1 d . . .
C12 C 0.3624(3) 0.3937(3) 0.3471(3) 0.0265(7) Uani 1 1 d . . .
H12A H 0.4381 0.4123 0.3266 0.040 Uiso 1 1 calc R . .
H12B H 0.2839 0.3517 0.2862 0.040 Uiso 1 1 calc R . .
H12C H 0.3851 0.3429 0.4004 0.040 Uiso 1 1 calc R . .
C13 C 0.4018(3) 0.6160(3) 0.3977(2) 0.0243(6) Uani 1 1 d . . .
H13 H 0.4748 0.6349 0.3777 0.029 Uiso 1 1 calc R . .
C14 C 0.3451(3) 0.6942(3) 0.4406(3) 0.0262(7) Uani 1 1 d . . .
H14 H 0.3727 0.7784 0.4556 0.031 Uiso 1 1 calc R . .
C15 C 0.1375(3) 0.4254(3) 0.4303(2) 0.0188(6) Uani 1 1 d . . .
H15 H 0.0793 0.4460 0.4630 0.023 Uiso 1 1 calc R . .
C16 C 0.0212(3) 0.1299(3) 0.3726(2) 0.0177(6) Uani 1 1 d . . .
H16 H 0.0826 0.1075 0.3440 0.021 Uiso 1 1 calc R . .
C17 C -0.0784(3) 0.0411(3) 0.3812(2) 0.0187(6) Uani 1 1 d . . .
C18 C -0.0134(3) -0.1422(3) 0.3077(2) 0.0236(6) Uani 1 1 d . . .
H18A H -0.0494 -0.2279 0.2918 0.035 Uiso 1 1 calc R . .
H18B H 0.0787 -0.1272 0.3592 0.035 Uiso 1 1 calc R . .
H18C H -0.0150 -0.1141 0.2439 0.035 Uiso 1 1 calc R . .
C19 C -0.1998(3) -0.1310(3) 0.3705(2) 0.0217(6) Uani 1 1 d . . .
H19 H -0.2351 -0.2138 0.3580 0.026 Uiso 1 1 calc R . .
C20 C -0.2433(3) -0.0399(3) 0.4131(2) 0.0216(6) Uani 1 1 d . . .
H20 H -0.3157 -0.0498 0.4349 0.026 Uiso 1 1 calc R . .
C21 C 0.5757(4) 0.4249(4) 0.1712(3) 0.0369(8) Uani 1 1 d . . .
C22 C 0.3780(3) -0.0095(3) 0.3221(3) 0.0306(7) Uani 1 1 d . . .
Ag1 Ag 0.13159(2) 0.71455(2) 0.537803(18) 0.02248(7) Uani 1 1 d . . .
Ag2 Ag 0.01288(2) 0.21069(2) 0.104774(19) 0.02228(7) Uani 1 1 d . . .
F1 F 0.4744(2) 0.4815(3) 0.1423(2) 0.0656(8) Uani 1 1 d . . .
F2 F 0.5354(3) 0.3273(2) 0.2037(2) 0.0565(7) Uani 1 1 d . . .
F3 F 0.6013(2) 0.3882(2) 0.08794(17) 0.0475(6) Uani 1 1 d . . .
F4 F 0.4270(2) -0.1098(2) 0.31256(18) 0.0401(5) Uani 1 1 d . . .
F5 F 0.4822(2) 0.0796(2) 0.36762(19) 0.0559(7) Uani 1 1 d . . .
F6 F 0.3156(3) -0.0229(3) 0.38706(19) 0.0627(8) Uani 1 1 d . . .
N1 N 0.8312(2) 0.4163(2) 0.8932(2) 0.0193(5) Uani 1 1 d . . .
N2 N 0.9417(2) 0.5738(2) 0.86292(19) 0.0201(5) Uani 1 1 d . . .
N3 N 0.8533(2) 0.7301(2) 0.97945(19) 0.0187(5) Uani 1 1 d . . .
N4 N 0.7950(2) 0.7978(2) 1.03459(19) 0.0189(5) Uani 1 1 d . . .
N5 N 0.6773(2) 0.9786(2) 1.12001(19) 0.0193(5) Uani 1 1 d . . .
N6 N 0.8453(2) 1.1127(2) 1.12677(19) 0.0176(5) Uani 1 1 d . . .
N7 N 0.3328(2) 0.5048(2) 0.3891(2) 0.0209(5) Uani 1 1 d . . .
N8 N 0.2427(2) 0.6334(2) 0.4589(2) 0.0209(5) Uani 1 1 d . . .
N9 N 0.1258(2) 0.3164(2) 0.3913(2) 0.0211(5) Uani 1 1 d . . .
N10 N 0.0245(2) 0.2413(2) 0.40487(19) 0.0194(5) Uani 1 1 d . . .
N11 N -0.0952(2) -0.0784(2) 0.34964(19) 0.0181(5) Uani 1 1 d . . .
N12 N -0.1679(2) 0.0672(2) 0.4197(2) 0.0206(5) Uani 1 1 d . . .
O1 O 0.8146(2) 0.4398(2) 0.3069(2) 0.0370(6) Uani 1 1 d . . .
O2 O 0.7600(3) 0.6071(2) 0.2183(2) 0.0430(7) Uani 1 1 d . . .
O3 O 0.6693(2) 0.5652(2) 0.34819(18) 0.0324(5) Uani 1 1 d . . .
O4 O 0.2198(3) 0.1208(2) 0.2236(2) 0.0382(6) Uani 1 1 d . . .
O5 O 0.1647(2) -0.0903(2) 0.1588(2) 0.0343(6) Uani 1 1 d . . .
O6 O 0.3518(2) 0.0270(3) 0.14118(19) 0.0374(6) Uani 1 1 d . . .
S1 S 0.72188(7) 0.51946(7) 0.27406(6) 0.02357(17) Uani 1 1 d . . .
S2 S 0.26617(7) 0.01509(7) 0.19715(6) 0.01942(15) 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'
Ag Ag -0.8971 1.1015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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
N2 C1 N1 111.1(3) . .
N2 C1 C5 123.5(3) . .
N1 C1 C5 125.4(3) . .
N1 C2 H2A 109.5 . .
N1 C2 H2B 109.5 . .
H2A C2 H2B 109.5 . .
N1 C2 H2C 109.5 . .
H2A C2 H2C 109.5 . .
H2B C2 H2C 109.5 . .
N1 C3 C4 106.1(3) . .
N1 C3 H3 126.9 . .
C4 C3 H3 126.9 . .
N2 C4 C3 109.6(3) . .
N2 C4 H4 125.2 . .
C3 C4 H4 125.2 . .
N3 C5 C1 118.1(3) . .
N3 C5 H5 121.0 . .
C1 C5 H5 121.0 . .
N4 C6 C7 121.8(3) . .
N4 C6 H6 119.1 . .
C7 C6 H6 119.1 . .
N6 C7 N5 110.4(2) . .
N6 C7 C6 122.7(3) . .
N5 C7 C6 126.9(3) . .
N5 C8 H8A 109.5 . .
N5 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
N5 C8 H8C 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
N5 C9 C10 106.8(3) . .
N5 C9 H9 126.6 . .
C10 C9 H9 126.6 . .
C9 C10 N6 109.1(3) . .
C9 C10 H10 125.4 . .
N6 C10 H10 125.4 . .
N8 C11 N7 110.3(3) . .
N8 C11 C15 122.3(3) . .
N7 C11 C15 127.4(3) . .
N7 C12 H12A 109.5 . .
N7 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
N7 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
C14 C13 N7 106.4(3) . .
C14 C13 H13 126.8 . .
N7 C13 H13 126.8 . .
C13 C14 N8 109.7(3) . .
C13 C14 H14 125.1 . .
N8 C14 H14 125.1 . .
N9 C15 C11 121.8(3) . .
N9 C15 H15 119.1 . .
C11 C15 H15 119.1 . .
N10 C16 C17 118.4(3) . .
N10 C16 H16 120.8 . .
C17 C16 H16 120.8 . .
N12 C17 N11 111.4(3) . .
N12 C17 C16 123.6(3) . .
N11 C17 C16 125.1(3) . .
N11 C18 H18A 109.5 . .
N11 C18 H18B 109.5 . .
H18A C18 H18B 109.5 . .
N11 C18 H18C 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
C20 C19 N11 106.0(3) . .
C20 C19 H19 127.0 . .
N11 C19 H19 127.0 . .
N12 C20 C19 110.5(3) . .
N12 C20 H20 124.8 . .
C19 C20 H20 124.8 . .
F1 C21 F3 108.8(3) . .
F1 C21 F2 106.7(3) . .
F3 C21 F2 107.3(3) . .
F1 C21 S1 111.0(3) . .
F3 C21 S1 111.6(3) . .
F2 C21 S1 111.2(3) . .
F5 C22 F6 108.4(3) . .
F5 C22 F4 107.0(3) . .
F6 C22 F4 106.1(3) . .
F5 C22 S2 112.0(3) . .
F6 C22 S2 111.7(2) . .
F4 C22 S2 111.3(2) . .
N8 Ag1 N10 165.25(10) . 2_566
N8 Ag1 N12 119.28(9) . 2_566
N10 Ag1 N12 73.16(9) 2_566 2_566
N6 Ag2 N3 158.08(9) 1_444 2_666
N6 Ag2 N2 120.81(9) 1_444 2_666
N3 Ag2 N2 72.77(9) 2_666 2_666
C1 N1 C3 107.2(2) . .
C1 N1 C2 127.9(3) . .
C3 N1 C2 124.9(3) . .
C1 N2 C4 105.9(3) . .
C1 N2 Ag2 108.45(19) . 2_666
C4 N2 Ag2 145.6(2) . 2_666
C5 N3 N4 112.4(2) . .
C5 N3 Ag2 117.3(2) . 2_666
N4 N3 Ag2 130.21(18) . 2_666
C6 N4 N3 112.1(2) . .
C7 N5 C9 107.6(2) . .
C7 N5 C8 127.7(3) . .
C9 N5 C8 124.6(2) . .
C7 N6 C10 106.1(2) . .
C7 N6 Ag2 131.22(19) . 1_666
C10 N6 Ag2 122.4(2) . 1_666
C11 N7 C13 107.6(2) . .
C11 N7 C12 128.1(3) . .
C13 N7 C12 124.3(3) . .
C11 N8 C14 106.0(3) . .
C11 N8 Ag1 129.4(2) . .
C14 N8 Ag1 124.4(2) . .
C15 N9 N10 112.4(2) . .
C16 N10 N9 111.6(2) . .
C16 N10 Ag1 118.02(19) . 2_566
N9 N10 Ag1 130.22(19) . 2_566
C17 N11 C19 106.9(2) . .
C17 N11 C18 127.7(3) . .
C19 N11 C18 125.2(3) . .
C17 N12 C20 105.3(2) . .
C17 N12 Ag1 106.78(19) . 2_566
C20 N12 Ag1 147.8(2) . 2_566
O1 S1 O3 116.78(15) . .
O1 S1 O2 113.90(16) . .
O3 S1 O2 114.76(16) . .
O1 S1 C21 103.72(16) . .
O3 S1 C21 103.22(16) . .
O2 S1 C21 101.79(19) . .
O6 S2 O5 114.63(16) . .
O6 S2 O4 116.36(17) . .
O5 S2 O4 113.90(15) . .
O6 S2 C22 102.43(15) . .
O5 S2 C22 104.02(16) . .
O4 S2 C22 103.10(16) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N2 1.332(4) .
C1 N1 1.355(4) .
C1 C5 1.451(4) .
C2 N1 1.466(4) .
C2 H2A 0.9800 .
C2 H2B 0.9800 .
C2 H2C 0.9800 .
C3 N1 1.366(4) .
C3 C4 1.379(4) .
C3 H3 0.9500 .
C4 N2 1.363(4) .
C4 H4 0.9500 .
C5 N3 1.287(4) .
C5 H5 0.9500 .
C6 N4 1.287(4) .
C6 C7 1.444(4) .
C6 H6 0.9500 .
C7 N6 1.334(4) .
C7 N5 1.358(4) .
C8 N5 1.472(4) .
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C8 H8C 0.9800 .
C9 N5 1.364(4) .
C9 C10 1.365(4) .
C9 H9 0.9500 .
C10 N6 1.378(4) .
C10 H10 0.9500 .
C11 N8 1.338(4) .
C11 N7 1.354(4) .
C11 C15 1.442(4) .
C12 N7 1.471(4) .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
C13 C14 1.361(5) .
C13 N7 1.366(4) .
C13 H13 0.9500 .
C14 N8 1.368(4) .
C14 H14 0.9500 .
C15 N9 1.280(4) .
C15 H15 0.9500 .
C16 N10 1.299(4) .
C16 C17 1.445(4) .
C16 H16 0.9500 .
C17 N12 1.333(4) .
C17 N11 1.361(4) .
C18 N11 1.465(4) .
C18 H18A 0.9800 .
C18 H18B 0.9800 .
C18 H18C 0.9800 .
C19 C20 1.370(4) .
C19 N11 1.370(4) .
C19 H19 0.9500 .
C20 N12 1.364(4) .
C20 H20 0.9500 .
C21 F1 1.315(4) .
C21 F3 1.335(4) .
C21 F2 1.340(5) .
C21 S1 1.823(4) .
C22 F5 1.332(4) .
C22 F6 1.338(4) .
C22 F4 1.346(4) .
C22 S2 1.806(3) .
Ag1 N8 2.152(2) .
Ag1 N10 2.231(2) 2_566
Ag1 N12 2.456(3) 2_566
Ag2 N6 2.170(2) 1_444
Ag2 N3 2.284(2) 2_666
Ag2 N2 2.418(3) 2_666
N2 Ag2 2.418(3) 2_666
N3 N4 1.403(3) .
N3 Ag2 2.284(2) 2_666
N6 Ag2 2.170(2) 1_666
N9 N10 1.401(3) .
N10 Ag1 2.231(2) 2_566
N12 Ag1 2.456(3) 2_566
O1 S1 1.438(2) .
O2 S1 1.453(3) .
O3 S1 1.445(2) .
O4 S2 1.437(2) .
O5 S2 1.435(2) .
O6 S2 1.433(2) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139045407
