#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:52:15 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301804 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/47/2214757.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2214757
loop_
_publ_author_name
'Wu, Yang-Jie'
'Liu, Xiu-Cun'
'Du, Chen-Xia'
'Niu, Yin-Yun'
_publ_section_title
;
 1,1'-(1,4-Phenylenedimethylene)dipyridinium bis(tetraphenylborate)
;
_journal_coeditor_code           IS2181
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3457
_journal_page_last               o3457
_journal_paper_doi               10.1107/S1600536807032588
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C18 H18 N2 2+, 2C24 H20 B -'
_chemical_formula_moiety         'C18 H18 N2 2+, 2(C24 H20 B -)'
_chemical_formula_sum            'C66 H58 B2 N2'
_chemical_formula_weight         900.76
_chemical_name_systematic
;
1,1'-(1,4-Phenylenedimethylene)dipyridinium bis(tetraphenylborate)
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                97.224(2)
_cell_angle_beta                 92.143(2)
_cell_angle_gamma                111.530(2)
_cell_formula_units_Z            1
_cell_length_a                   9.8194(8)
_cell_length_b                   10.3074(9)
_cell_length_c                   13.3980(12)
_cell_measurement_reflns_used    1607
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.99
_cell_measurement_theta_min      1.54
_cell_volume                     1246.28(19)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2001)'
_computing_data_collection       'APEX2 (Bruker, 2001)'
_computing_data_reduction        SAINT-Plus
_computing_molecular_graphics    'SHELXTL (Bruker, 2001)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker APEX II CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0382
_diffrn_reflns_av_sigmaI/netI    0.0646
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9445
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         1.54
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.200
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             478
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.177
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         4794
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0946
_refine_ls_R_factor_gt           0.0583
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0666P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1312
_refine_ls_wR_factor_ref         0.1486
_reflns_number_gt                3179
_reflns_number_total             4794
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            is2181.cif
_cod_data_source_block           I
_cod_database_code               2214757
_cod_database_fobs_code          2214757
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
B B1 0.2031(2) 0.5217(2) 0.23828(15) 0.0340(5) Uani d . 1
C C1 0.6064(2) 0.9191(2) 0.28743(14) 0.0455(6) Uani d . 1
H H1 0.5622 0.8386 0.3171 0.055 Uiso calc R 1
C C2 0.5276(2) 0.9974(2) 0.26334(15) 0.0499(6) Uani d . 1
H H2 0.4295 0.9705 0.2767 0.060 Uiso calc R 1
C C3 0.5923(3) 1.1152(2) 0.21966(16) 0.0551(6) Uani d . 1
H H3 0.5396 1.1701 0.2046 0.066 Uiso calc R 1
C C4 0.7366(3) 1.1521(2) 0.19802(16) 0.0552(6) Uani d . 1
H H4 0.7814 1.2308 0.1667 0.066 Uiso calc R 1
C C5 0.8125(2) 1.0725(2) 0.22287(16) 0.0505(6) Uani d . 1
H H5 0.9099 1.0967 0.2085 0.061 Uiso calc R 1
C C6 0.8356(3) 0.8804(2) 0.30283(16) 0.0551(6) Uani d . 1
H H6A 0.9058 0.8784 0.2542 0.066 Uiso calc R 1
H H6B 0.7710 0.7838 0.3052 0.066 Uiso calc R 1
C C7 0.9178(2) 0.9449(2) 0.40600(15) 0.0422(5) Uani d . 1
C C8 0.9777(2) 0.8658(2) 0.45543(16) 0.0507(6) Uani d . 1
H H8 0.9631 0.7745 0.4260 0.061 Uiso calc R 1
C C9 1.0587(3) 0.9201(2) 0.54765(17) 0.0539(6) Uani d . 1
H H9 1.0984 0.8650 0.5793 0.065 Uiso calc R 1
C C10 0.2930(2) 0.61470(19) 0.15340(13) 0.0339(5) Uani d . 1
C C11 0.4208(2) 0.5992(2) 0.12074(14) 0.0415(5) Uani d . 1
H H11 0.4465 0.5281 0.1420 0.050 Uiso calc R 1
C C12 0.5106(2) 0.6841(2) 0.05859(16) 0.0500(6) Uani d . 1
H H12 0.5949 0.6701 0.0396 0.060 Uiso calc R 1
C C13 0.4750(3) 0.7892(2) 0.02493(15) 0.0529(6) Uani d . 1
H H13 0.5346 0.8467 -0.0171 0.064 Uiso calc R 1
C C14 0.3507(3) 0.8083(2) 0.05401(16) 0.0509(6) Uani d . 1
H H14 0.3252 0.8786 0.0311 0.061 Uiso calc R 1
C C15 0.2626(2) 0.7235(2) 0.11752(14) 0.0420(5) Uani d . 1
H H15 0.1797 0.7399 0.1370 0.050 Uiso calc R 1
C C16 0.3055(2) 0.60729(18) 0.34397(13) 0.0335(5) Uani d . 1
C C17 0.4272(2) 0.5815(2) 0.38034(14) 0.0395(5) Uani d . 1
H H17 0.4453 0.5050 0.3478 0.047 Uiso calc R 1
C C18 0.5221(2) 0.6652(2) 0.46290(16) 0.0507(6) Uani d . 1
H H18 0.6019 0.6443 0.4844 0.061 Uiso calc R 1
C C19 0.4984(3) 0.7787(2) 0.51278(16) 0.0578(7) Uani d . 1
H H19 0.5613 0.8347 0.5683 0.069 Uiso calc R 1
C C20 0.3803(3) 0.8085(2) 0.47958(16) 0.0552(6) Uani d . 1
H H20 0.3636 0.8856 0.5125 0.066 Uiso calc R 1
C C21 0.2863(2) 0.7241(2) 0.39730(14) 0.0425(5) Uani d . 1
H H21 0.2069 0.7461 0.3766 0.051 Uiso calc R 1
C C22 0.1924(2) 0.35750(19) 0.21150(14) 0.0371(5) Uani d . 1
C C23 0.1626(2) 0.2894(2) 0.11149(17) 0.0548(6) Uani d . 1
H H23 0.1498 0.3392 0.0610 0.066 Uiso calc R 1
C C24 0.1514(3) 0.1520(3) 0.0841(2) 0.0778(9) Uani d . 1
H H24 0.1314 0.1112 0.0165 0.093 Uiso calc R 1
C C25 0.1699(3) 0.0756(3) 0.1571(3) 0.0847(10) Uani d . 1
H H25 0.1644 -0.0165 0.1391 0.102 Uiso calc R 1
C C26 0.1965(3) 0.1365(3) 0.2568(3) 0.0727(8) Uani d . 1
H H26 0.2087 0.0857 0.3068 0.087 Uiso calc R 1
C C27 0.2053(2) 0.2746(2) 0.28269(18) 0.0525(6) Uani d . 1
H H27 0.2205 0.3131 0.3507 0.063 Uiso calc R 1
C C28 0.0339(2) 0.51288(19) 0.24453(14) 0.0367(5) Uani d . 1
C C29 -0.0361(2) 0.4910(2) 0.33345(16) 0.0471(6) Uani d . 1
H H29 0.0169 0.4856 0.3907 0.056 Uiso calc R 1
C C30 -0.1818(3) 0.4770(2) 0.3396(2) 0.0636(7) Uani d . 1
H H30 -0.2243 0.4625 0.4001 0.076 Uiso calc R 1
C C31 -0.2631(3) 0.4847(3) 0.2560(2) 0.0695(8) Uani d . 1
H H31 -0.3598 0.4778 0.2602 0.083 Uiso calc R 1
C C32 -0.2002(3) 0.5025(2) 0.1667(2) 0.0633(7) Uani d . 1
H H32 -0.2547 0.5061 0.1095 0.076 Uiso calc R 1
C C33 -0.0560(2) 0.5152(2) 0.16148(17) 0.0478(6) Uani d . 1
H H33 -0.0163 0.5259 0.0997 0.057 Uiso calc R 1
N N1 0.74748(19) 0.95834(17) 0.26829(12) 0.0426(4) Uani d . 1
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'
B B 0.0013 0.0007 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C28 B1 C10 . . 114.81(16)
C28 B1 C22 . . 106.03(15)
C10 B1 C22 . . 109.62(16)
C28 B1 C16 . . 111.05(15)
C10 B1 C16 . . 101.99(14)
C22 B1 C16 . . 113.55(16)
N1 C1 C2 . . 119.8(2)
N1 C1 H1 . . 120.1
C2 C1 H1 . . 120.1
C1 C2 C3 . . 120.1(2)
C1 C2 H2 . . 120.0
C3 C2 H2 . . 120.0
C2 C3 C4 . . 119.4(2)
C2 C3 H3 . . 120.3
C4 C3 H3 . . 120.3
C5 C4 C3 . . 119.3(2)
C5 C4 H4 . . 120.4
C3 C4 H4 . . 120.4
N1 C5 C4 . . 120.4(2)
N1 C5 H5 . . 119.8
C4 C5 H5 . . 119.8
N1 C6 C7 . . 112.98(16)
N1 C6 H6A . . 109.0
C7 C6 H6A . . 109.0
N1 C6 H6B . . 109.0
C7 C6 H6B . . 109.0
H6A C6 H6B . . 107.8
C8 C7 C9 . 2_776 117.79(19)
C8 C7 C6 . . 118.02(18)
C9 C7 C6 2_776 . 124.15(19)
C9 C8 C7 . . 121.02(19)
C9 C8 H8 . . 119.5
C7 C8 H8 . . 119.5
C8 C9 C7 . 2_776 121.2(2)
C8 C9 H9 . . 119.4
C7 C9 H9 2_776 . 119.4
C15 C10 C11 . . 114.40(18)
C15 C10 B1 . . 125.01(18)
C11 C10 B1 . . 120.16(17)
C12 C11 C10 . . 123.4(2)
C12 C11 H11 . . 118.3
C10 C11 H11 . . 118.3
C13 C12 C11 . . 119.8(2)
C13 C12 H12 . . 120.1
C11 C12 H12 . . 120.1
C14 C13 C12 . . 119.2(2)
C14 C13 H13 . . 120.4
C12 C13 H13 . . 120.4
C13 C14 C15 . . 120.4(2)
C13 C14 H14 . . 119.8
C15 C14 H14 . . 119.8
C14 C15 C10 . . 122.8(2)
C14 C15 H15 . . 118.6
C10 C15 H15 . . 118.6
C21 C16 C17 . . 114.86(16)
C21 C16 B1 . . 121.03(17)
C17 C16 B1 . . 123.67(16)
C18 C17 C16 . . 122.81(19)
C18 C17 H17 . . 118.6
C16 C17 H17 . . 118.6
C19 C18 C17 . . 120.1(2)
C19 C18 H18 . . 120.0
C17 C18 H18 . . 120.0
C18 C19 C20 . . 119.19(19)
C18 C19 H19 . . 120.4
C20 C19 H19 . . 120.4
C19 C20 C21 . . 120.2(2)
C19 C20 H20 . . 119.9
C21 C20 H20 . . 119.9
C20 C21 C16 . . 122.9(2)
C20 C21 H21 . . 118.6
C16 C21 H21 . . 118.6
C27 C22 C23 . . 114.86(19)
C27 C22 B1 . . 124.77(17)
C23 C22 B1 . . 120.32(18)
C24 C23 C22 . . 123.2(2)
C24 C23 H23 . . 118.4
C22 C23 H23 . . 118.4
C25 C24 C23 . . 119.8(3)
C25 C24 H24 . . 120.1
C23 C24 H24 . . 120.1
C26 C25 C24 . . 119.4(2)
C26 C25 H25 . . 120.3
C24 C25 H25 . . 120.3
C25 C26 C27 . . 119.7(3)
C25 C26 H26 . . 120.1
C27 C26 H26 . . 120.1
C22 C27 C26 . . 122.9(2)
C22 C27 H27 . . 118.5
C26 C27 H27 . . 118.5
C29 C28 C33 . . 114.58(19)
C29 C28 B1 . . 121.42(17)
C33 C28 B1 . . 123.82(18)
C30 C29 C28 . . 122.6(2)
C30 C29 H29 . . 118.7
C28 C29 H29 . . 118.7
C31 C30 C29 . . 120.0(2)
C31 C30 H30 . . 120.0
C29 C30 H30 . . 120.0
C32 C31 C30 . . 119.3(2)
C32 C31 H31 . . 120.3
C30 C31 H31 . . 120.3
C31 C32 C33 . . 120.0(2)
C31 C32 H32 . . 120.0
C33 C32 H32 . . 120.0
C32 C33 C28 . . 123.4(2)
C32 C33 H33 . . 118.3
C28 C33 H33 . . 118.3
C1 N1 C5 . . 121.03(19)
C1 N1 C6 . . 119.39(18)
C5 N1 C6 . . 119.48(19)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
B1 C28 . 1.637(3)
B1 C10 . 1.649(3)
B1 C22 . 1.649(3)
B1 C16 . 1.650(3)
C1 N1 . 1.338(3)
C1 C2 . 1.364(3)
C1 H1 . 0.9300
C2 C3 . 1.364(3)
C2 H2 . 0.9300
C3 C4 . 1.378(3)
C3 H3 . 0.9300
C4 C5 . 1.356(3)
C4 H4 . 0.9300
C5 N1 . 1.349(3)
C5 H5 . 0.9300
C6 N1 . 1.477(3)
C6 C7 . 1.515(3)
C6 H6A . 0.9700
C6 H6B . 0.9700
C7 C8 . 1.381(3)
C7 C9 2_776 1.383(3)
C8 C9 . 1.378(3)
C8 H8 . 0.9300
C9 C7 2_776 1.383(3)
C9 H9 . 0.9300
C10 C15 . 1.396(3)
C10 C11 . 1.401(3)
C11 C12 . 1.381(3)
C11 H11 . 0.9300
C12 C13 . 1.375(3)
C12 H12 . 0.9300
C13 C14 . 1.368(3)
C13 H13 . 0.9300
C14 C15 . 1.387(3)
C14 H14 . 0.9300
C15 H15 . 0.9300
C16 C21 . 1.399(3)
C16 C17 . 1.399(3)
C17 C18 . 1.389(3)
C17 H17 . 0.9300
C18 C19 . 1.373(3)
C18 H18 . 0.9300
C19 C20 . 1.376(3)
C19 H19 . 0.9300
C20 C21 . 1.385(3)
C20 H20 . 0.9300
C21 H21 . 0.9300
C22 C27 . 1.390(3)
C22 C23 . 1.399(3)
C23 C24 . 1.380(3)
C23 H23 . 0.9300
C24 C25 . 1.377(4)
C24 H24 . 0.9300
C25 C26 . 1.375(4)
C25 H25 . 0.9300
C26 C27 . 1.392(3)
C26 H26 . 0.9300
C27 H27 . 0.9300
C28 C29 . 1.399(3)
C28 C33 . 1.402(3)
C29 C30 . 1.391(3)
C29 H29 . 0.9300
C30 C31 . 1.379(4)
C30 H30 . 0.9300
C31 C32 . 1.369(4)
C31 H31 . 0.9300
C32 C33 . 1.378(3)
C32 H32 . 0.9300
C33 H33 . 0.9300
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C9 H9 N1 2_776 0.93 2.57 2.897(3) 101
C1 H1 Cg1 1_555 0.93 2.44 3.313(2) 156
C4 H4 Cg3 1_665 0.93 2.63 3.280(2) 127
C5 H5 Cg2 1_665 0.93 2.53 3.446(2) 168
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_site_symmetry_1
_geom_torsion_site_symmetry_4
_geom_torsion
N1 C1 C2 C3 . . 0.1(3)
C1 C2 C3 C4 . . 1.6(3)
C2 C3 C4 C5 . . -1.6(3)
C3 C4 C5 N1 . . 0.0(3)
N1 C6 C7 C8 . . 166.3(2)
N1 C6 C7 C9 . 2_776 -16.1(3)
C9 C7 C8 C9 2_776 . -0.3(4)
C6 C7 C8 C9 . . 177.4(2)
C7 C8 C9 C7 . 2_776 0.3(4)
C28 B1 C10 C15 . . 25.6(2)
C22 B1 C10 C15 . . 144.80(17)
C16 B1 C10 C15 . . -94.6(2)
C28 B1 C10 C11 . . -162.31(15)
C22 B1 C10 C11 . . -43.1(2)
C16 B1 C10 C11 . . 77.51(19)
C15 C10 C11 C12 . . 0.3(3)
B1 C10 C11 C12 . . -172.63(17)
C10 C11 C12 C13 . . -0.7(3)
C11 C12 C13 C14 . . 0.2(3)
C12 C13 C14 C15 . . 0.7(3)
C13 C14 C15 C10 . . -1.1(3)
C11 C10 C15 C14 . . 0.6(3)
B1 C10 C15 C14 . . 173.11(17)
C28 B1 C16 C21 . . -37.3(2)
C10 B1 C16 C21 . . 85.5(2)
C22 B1 C16 C21 . . -156.69(17)
C28 B1 C16 C17 . . 150.74(18)
C10 B1 C16 C17 . . -86.5(2)
C22 B1 C16 C17 . . 31.4(3)
C21 C16 C17 C18 . . -0.1(3)
B1 C16 C17 C18 . . 172.29(19)
C16 C17 C18 C19 . . 0.2(3)
C17 C18 C19 C20 . . -0.4(3)
C18 C19 C20 C21 . . 0.5(3)
C19 C20 C21 C16 . . -0.4(3)
C17 C16 C21 C20 . . 0.2(3)
B1 C16 C21 C20 . . -172.40(19)
C28 B1 C22 C27 . . -94.2(2)
C10 B1 C22 C27 . . 141.32(19)
C16 B1 C22 C27 . . 28.0(3)
C28 B1 C22 C23 . . 83.1(2)
C10 B1 C22 C23 . . -41.4(2)
C16 B1 C22 C23 . . -154.74(18)
C27 C22 C23 C24 . . -2.1(3)
B1 C22 C23 C24 . . -179.6(2)
C22 C23 C24 C25 . . 0.0(4)
C23 C24 C25 C26 . . 1.3(4)
C24 C25 C26 C27 . . -0.4(4)
C23 C22 C27 C26 . . 3.0(3)
B1 C22 C27 C26 . . -179.58(19)
C25 C26 C27 C22 . . -1.9(4)
C10 B1 C28 C29 . . -153.73(17)
C22 B1 C28 C29 . . 85.1(2)
C16 B1 C28 C29 . . -38.7(2)
C10 B1 C28 C33 . . 31.4(2)
C22 B1 C28 C33 . . -89.8(2)
C16 B1 C28 C33 . . 146.43(18)
C33 C28 C29 C30 . . -1.8(3)
B1 C28 C29 C30 . . -177.17(18)
C28 C29 C30 C31 . . -0.1(3)
C29 C30 C31 C32 . . 1.6(4)
C30 C31 C32 C33 . . -1.2(4)
C31 C32 C33 C28 . . -0.9(3)
C29 C28 C33 C32 . . 2.4(3)
B1 C28 C33 C32 . . 177.55(19)
C2 C1 N1 C5 . . -1.8(3)
C2 C1 N1 C6 . . 174.56(17)
C4 C5 N1 C1 . . 1.7(3)
C4 C5 N1 C6 . . -174.63(18)
C7 C6 N1 C1 . . -92.6(2)
C7 C6 N1 C5 . . 83.8(2)
loop_
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1 PubChem 139072736
