#------------------------------------------------------------------------------
#$Date: 2024-10-31 04:58:58 +0200 (Thu, 31 Oct 2024) $
#$Revision: 295687 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/31/26/2312674.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_2312674
loop_
_publ_author_name
'Steinke, Tim'
'Engelage, Elric'
'Huber, Stefan M.'
_publ_section_title
;
 Chalcogen bonding in the solid-state structures of
 1,3-bis(benzimidazoliumyl)benzene-based chalcogen-bonding donors.
;
_journal_coeditor_code           QW3003
_journal_issue                   'Pt 2'
_journal_name_full
'Acta crystallographica. Section C, Structural chemistry'
_journal_page_first              26
_journal_page_last               35
_journal_paper_doi               10.1107/S2053229622011536
_journal_volume                  79
_journal_year                    2023
_chemical_formula_iupac          'C24 H24 N4 Se2 2+, 2C F3 O3 S -, 0.5C2 H4 Cl2'
_chemical_formula_moiety
'C24 H24 N4 Se2 2+, 2(C F3 O3 S -), 0.5(C2 H4 Cl2)'
_chemical_formula_sum            'C27 H26 Cl F6 N4 O6 S2 Se2'
_chemical_formula_weight         874.01
_chemical_name_systematic
;
3,3'-Bis(methylselanyl)-1,1'-(1,3-phenylene)bis(1H-1,3-benzodiazol-3-ium)
bis(trifluoromethanesulfonate) 1,2-dichloroethane hemisolvate
;
_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   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                102.5150(10)
_cell_angle_beta                 93.2310(10)
_cell_angle_gamma                96.1980(10)
_cell_formula_units_Z            2
_cell_length_a                   9.36720(10)
_cell_length_b                   13.3265(2)
_cell_length_c                   13.64450(10)
_cell_measurement_reflns_used    5795
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      66.5
_cell_measurement_theta_min      3.3
_cell_volume                     1647.49(3)
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2018)
;
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2018)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2018)
;
_computing_molecular_graphics
;
DIAMOND (Putz & Brandenburg, 2014) and Mercury (Macrae et al.,
2020)
;
_computing_publication_material
;
WinGX (Farrugia, 2012)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a) and shelXle (Hübschle et al.,
2011)
;
_diffrn_ambient_temperature      170.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'Rigaku XtaLAB Synergy Dualflex diffractometer with a HyPix detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0462
_diffrn_reflns_av_unetI/netI     0.0435
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            19605
_diffrn_reflns_theta_full        66.498
_diffrn_reflns_theta_max         66.498
_diffrn_reflns_theta_min         3.329
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    5.478
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.456
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2018)
;
_exptl_crystal_colour            'translucent colourless'
_exptl_crystal_density_diffrn    1.762
_exptl_crystal_description       'cut plate'
_exptl_crystal_F_000             870
_exptl_crystal_size_max          0.189
_exptl_crystal_size_mid          0.096
_exptl_crystal_size_min          0.078
_refine_diff_density_max         0.841
_refine_diff_density_min         -0.795
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     484
_refine_ls_number_reflns         5795
_refine_ls_number_restraints     28
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0480
_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)+(0.0607P)²+3.3756P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1244
_refine_ls_wR_factor_ref         0.1272
_reflns_number_gt                5307
_reflns_number_total             5795
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            qw3003.cif
_cod_data_source_block           TS-056_3Se-C
_cod_database_code               2312674
_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.
;
loop_
_space_group_symop_operation_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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Se Se1A 0.51229(5) 0.78078(3) 0.20663(3) 0.03655(15) Uani d 0.9498(10) A 1
N N1A 0.3629(6) 0.7664(3) 0.3822(3) 0.0317(8) Uani d 0.9498(10) A 1
N N2A 0.4146(11) 0.6162(3) 0.3040(4) 0.0261(7) Uani d 0.9498(10) A 1
C C1A 0.7037(5) 0.7379(4) 0.2166(3) 0.0420(10) Uani d 0.9498(10) A 1
H H1AA 0.764582 0.768208 0.171733 0.063 Uiso calc 0.9498(10) A 1
H H1AB 0.696569 0.662222 0.196995 0.063 Uiso calc 0.9498(10) A 1
H H1AC 0.746273 0.761771 0.286196 0.063 Uiso calc 0.9498(10) A 1
C C3A 0.4277(7) 0.7173(3) 0.3041(3) 0.0282(10) Uani d 0.9498(10) A 1
C C4A 0.3515(9) 0.8774(4) 0.4098(6) 0.0499(17) Uani d 0.9498(10) A 1
H H4AA 0.360353 0.900770 0.483322 0.075 Uiso calc 0.9498(10) A 1
H H4AB 0.257903 0.890591 0.382867 0.075 Uiso calc 0.9498(10) A 1
H H4AC 0.428760 0.915132 0.381636 0.075 Uiso calc 0.9498(10) A 1
C C5A 0.3027(4) 0.6943(3) 0.4323(3) 0.0315(8) Uani d 0.9498(10) A 1
C C6A 0.2161(5) 0.7041(4) 0.5138(3) 0.0423(11) Uani d 0.9498(10) A 1
H H6A 0.190937 0.769239 0.547424 0.051 Uiso calc 0.9498(10) A 1
C C7A 0.1696(5) 0.6134(4) 0.5419(3) 0.0455(11) Uani d 0.9498(10) A 1
H H7A 0.108846 0.616114 0.595601 0.055 Uiso calc 0.9498(10) A 1
C C8A 0.2087(5) 0.5180(4) 0.4944(5) 0.0421(12) Uani d 0.9498(10) A 1
H H8A 0.176484 0.458318 0.518278 0.051 Uiso calc 0.9498(10) A 1
C C9A 0.2924(4) 0.5074(3) 0.4139(3) 0.0341(9) Uani d 0.9498(10) A 1
H H9A 0.317749 0.442275 0.380633 0.041 Uiso calc 0.9498(10) A 1
C C10A 0.3373(5) 0.5987(4) 0.3846(3) 0.0283(11) Uani d 0.9498(10) A 1
Se Se1B 0.3520(10) 0.4679(6) 0.4492(6) 0.03655(15) Uani d 0.0502(10) A 2
C C1B 0.170(9) 0.503(11) 0.499(13) 0.0420(10) Uani d 0.0502(10) A 2
H H1BA 0.154002 0.571836 0.488350 0.063 Uiso calc 0.0502(10) A 2
H H1BB 0.171045 0.503692 0.570562 0.063 Uiso calc 0.0502(10) A 2
H H1BC 0.091254 0.451706 0.461725 0.063 Uiso calc 0.0502(10) A 2
N N1B 0.314376 0.678949 0.447267 0.0317(8) Uani d 0.0502(10) A 2
N N2B 0.41(2) 0.604(4) 0.312(8) 0.0261(7) Uani d 0.0502(10) A 2
C C3B 0.359(15) 0.590(4) 0.400(5) 0.0282(10) Uani d 0.0502(10) A 2
C C4B 0.262(13) 0.702(6) 0.547(4) 0.0499(17) Uani d 0.0502(10) A 2
H H4BA 0.267257 0.777660 0.571149 0.075 Uiso calc 0.0502(10) A 2
H H4BB 0.320596 0.674078 0.593420 0.075 Uiso calc 0.0502(10) A 2
H H4BC 0.161140 0.671305 0.543359 0.075 Uiso calc 0.0502(10) A 2
C C5B 0.341(16) 0.762(5) 0.403(8) 0.0315(8) Uani d 0.0502(10) A 2
C C6B 0.322(19) 0.867(6) 0.417(9) 0.0423(11) Uani d 0.0502(10) A 2
H H6B 0.282495 0.904160 0.474158 0.051 Uiso calc 0.0502(10) A 2
C C7B 0.366(9) 0.912(4) 0.340(5) 0.0455(11) Uani d 0.0502(10) A 2
H H7B 0.340495 0.978647 0.338420 0.055 Uiso calc 0.0502(10) A 2
C C8B 0.446(8) 0.864(4) 0.264(4) 0.0421(12) Uani d 0.0502(10) A 2
H H8B 0.482276 0.901547 0.216517 0.051 Uiso calc 0.0502(10) A 2
C C9B 0.474(8) 0.763(4) 0.257(5) 0.0341(9) Uani d 0.0502(10) A 2
H H9B 0.532521 0.731073 0.207871 0.041 Uiso calc 0.0502(10) A 2
C C10B 0.413(16) 0.712(4) 0.325(8) 0.0283(11) Uani d 0.0502(10) A 2
C C2A 0.9577(5) 0.5809(3) 0.2775(3) 0.0440(10) Uani d 1 . .
H H2AA 1.000622 0.651134 0.276882 0.066 Uiso calc 1 . .
H H2AB 1.022288 0.549576 0.317907 0.066 Uiso calc 1 . .
H H2AC 0.864711 0.583860 0.306753 0.066 Uiso calc 1 . .
N N3 0.7211(3) 0.3466(2) 0.1936(2) 0.0279(6) Uani d 1 . .
N N4 0.9361(3) 0.2978(2) 0.1916(2) 0.0311(6) Uani d 1 . .
Se Se2 0.92896(4) 0.49697(3) 0.13920(3) 0.03528(14) Uani d 1 . .
C C11 0.8597(4) 0.3727(3) 0.1769(3) 0.0293(7) Uani d 1 . .
C C12 1.0894(4) 0.2924(4) 0.1769(3) 0.0410(9) Uani d 1 . .
H H12A 1.139658 0.284118 0.239078 0.062 Uiso calc 1 . .
H H12B 1.131541 0.356278 0.159712 0.062 Uiso calc 1 . .
H H12C 1.099365 0.233066 0.122044 0.062 Uiso calc 1 . .
C C13 0.8453(4) 0.2191(3) 0.2166(3) 0.0312(8) Uani d 1 . .
C C14 0.8724(5) 0.1257(3) 0.2395(3) 0.0389(9) Uani d 1 . .
H H14 0.965944 0.104311 0.238527 0.047 Uiso calc 1 . .
C C15 0.7561(5) 0.0660(3) 0.2636(3) 0.0443(10) Uani d 1 . .
H H15 0.769564 0.001151 0.278621 0.053 Uiso calc 1 . .
C C16 0.6181(5) 0.0981(3) 0.2668(3) 0.0445(10) Uani d 1 . .
H H16 0.541410 0.054914 0.285092 0.053 Uiso calc 1 . .
C C17 0.5906(5) 0.1913(3) 0.2439(3) 0.0384(9) Uani d 1 . .
H H17 0.497432 0.213314 0.245928 0.046 Uiso calc 1 . .
C C18 0.7082(4) 0.2503(3) 0.2177(3) 0.0310(8) Uani d 1 . .
C C19 0.4537(4) 0.5337(3) 0.2273(2) 0.0260(7) Uani d 1 . .
C C20 0.3729(4) 0.5062(3) 0.1355(3) 0.0321(8) Uani d 1 . .
H H20 0.295222 0.542871 0.122199 0.039 Uiso calc 1 . .
C C21 0.4075(5) 0.4237(3) 0.0631(3) 0.0385(9) Uani d 1 . .
H H21 0.351792 0.402888 0.000176 0.046 Uiso calc 1 . .
C C22 0.5228(4) 0.3717(3) 0.0820(3) 0.0332(8) Uani d 1 . .
H H22 0.547201 0.315945 0.032132 0.040 Uiso calc 1 . .
C C23 0.6021(4) 0.4021(3) 0.1748(3) 0.0279(7) Uani d 1 . .
C C24 0.5678(4) 0.4821(3) 0.2498(3) 0.0270(7) Uani d 1 . .
H H24 0.620428 0.500739 0.313983 0.032 Uiso calc 1 . .
S S1 0.11819(10) 0.75468(7) 0.09579(7) 0.0331(2) Uani d 1 . .
F F1 0.2088(4) 0.9489(3) 0.1760(3) 0.0861(12) Uani d 1 . .
F F2 -0.0039(4) 0.8998(3) 0.2082(3) 0.0947(14) Uani d 1 . .
F F3 0.0356(5) 0.9246(3) 0.0616(4) 0.1094(15) Uani d 1 . .
O O1 0.1765(4) 0.7316(3) 0.1871(2) 0.0558(8) Uani d 1 . .
O O2 0.2189(3) 0.7585(3) 0.0206(2) 0.0495(8) Uani d 1 . .
O O3 -0.0227(4) 0.7008(3) 0.0599(2) 0.0528(8) Uani d 1 . .
C C25 0.0879(6) 0.8895(4) 0.1370(5) 0.0594(13) Uani d 1 . .
F F4 0.0437(4) 0.1670(4) 0.5413(5) 0.126(2) Uani d 1 . .
F F5 0.2090(5) 0.0786(3) 0.5591(3) 0.0908(12) Uani d 1 . .
F F6 0.0937(4) 0.0531(2) 0.4146(3) 0.0793(10) Uani d 1 . .
C C26 0.1483(5) 0.1260(4) 0.4950(4) 0.0552(12) Uani d 1 . .
Cl Cl1A 0.352(2) 0.1088(13) -0.0121(18) 0.062(2) Uani d 0.574(10) B 1
C C27A 0.5136(10) 0.0490(7) -0.0184(7) 0.0509(18) Uani d 0.574(10) B 1
H H27A 0.540977 0.033300 -0.088571 0.061 Uiso calc 0.574(10) B 1
H H27B 0.593142 0.096079 0.024336 0.061 Uiso calc 0.574(10) B 1
Cl Cl1B 0.345(3) 0.1106(19) 0.003(2) 0.067(5) Uani d 0.426(10) B 2
C C27B 0.4228(14) -0.0051(10) 0.0141(9) 0.0509(18) Uani d 0.426(10) B 2
H H27C 0.420525 -0.014172 0.084101 0.061 Uiso calc 0.426(10) B 2
H H27D 0.366556 -0.066503 -0.031233 0.061 Uiso calc 0.426(10) B 2
S S2A 0.2594(6) 0.2311(5) 0.4639(5) 0.0436(9) Uani d 0.480(4) C 1
O O4A 0.3166(4) 0.2966(3) 0.5527(3) 0.0635(7) Uani d 0.480(4) C 1
O O5A 0.1604(10) 0.2659(6) 0.4004(6) 0.0635(7) Uani d 0.480(4) C 1
O O6A 0.3731(9) 0.1796(7) 0.4160(6) 0.0635(7) Uani d 0.480(4) C 1
S S2B 0.2967(6) 0.2109(5) 0.4596(5) 0.0436(9) Uani d 0.520(4) C 2
O O4B 0.3166(4) 0.2966(3) 0.5527(3) 0.0635(7) Uani d 0.520(4) C 2
O O5B 0.2447(9) 0.2429(6) 0.3721(5) 0.0635(7) Uani d 0.520(4) C 2
O O6B 0.4035(8) 0.1392(6) 0.4430(6) 0.0635(7) Uani d 0.520(4) C 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.7943 1.1372 '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'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 -1 2 0.0605
-6 2 0 0.0997
3 1 -8 0.0432
-1 -8 0 0.0361
0 7 4 0.0403
0 1 -1 0.0239
0 0 0 0.0372
0 0 0 0.0410
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
_geom_angle_publ_flag
C3A Se1A C1A . . 99.1(2) ?
C3A N1A C5A . . 108.9(3) ?
C3A N1A C4A . . 126.5(4) ?
C5A N1A C4A . . 124.6(3) ?
C3A N2A C10A . . 109.4(3) ?
C3A N2A C19 . . 127.2(3) ?
C10A N2A C19 . . 122.9(4) ?
Se1A C1A H1AA . . 109.5 ?
Se1A C1A H1AB . . 109.5 ?
H1AA C1A H1AB . . 109.5 ?
Se1A C1A H1AC . . 109.5 ?
H1AA C1A H1AC . . 109.5 ?
H1AB C1A H1AC . . 109.5 ?
N1A C3A N2A . . 108.6(3) ?
N1A C3A Se1A . . 124.8(3) ?
N2A C3A Se1A . . 126.5(3) ?
N1A C4A H4AA . . 109.5 ?
N1A C4A H4AB . . 109.5 ?
H4AA C4A H4AB . . 109.5 ?
N1A C4A H4AC . . 109.5 ?
H4AA C4A H4AC . . 109.5 ?
H4AB C4A H4AC . . 109.5 ?
C10A C5A N1A . . 107.4(4) ?
C10A C5A C6A . . 120.9(4) ?
N1A C5A C6A . . 131.7(4) ?
C7A C6A C5A . . 115.9(4) ?
C7A C6A H6A . . 122.0 ?
C5A C6A H6A . . 122.0 ?
C6A C7A C8A . . 122.4(4) ?
C6A C7A H7A . . 118.8 ?
C8A C7A H7A . . 118.8 ?
C9A C8A C7A . . 122.2(5) ?
C9A C8A H8A . . 118.9 ?
C7A C8A H8A . . 118.9 ?
C8A C9A C10A . . 115.4(4) ?
C8A C9A H9A . . 122.3 ?
C10A C9A H9A . . 122.3 ?
C5A C10A C9A . . 123.2(4) ?
C5A C10A N2A . . 105.7(4) ?
C9A C10A N2A . . 131.0(4) ?
C3B Se1B C1B . . 86(5) ?
Se1B C1B H1BA . . 109.5 ?
Se1B C1B H1BB . . 109.5 ?
H1BA C1B H1BB . . 109.5 ?
Se1B C1B H1BC . . 109.5 ?
H1BA C1B H1BC . . 109.5 ?
H1BB C1B H1BC . . 109.5 ?
C3B N1B C5B . . 116(4) ?
C3B N1B C4B . . 128(3) ?
C5B N1B C4B . . 116(4) ?
C3B N2B C10B . . 102(4) ?
C3B N2B C19 . . 132(3) ?
C10B N2B C19 . . 126(4) ?
N1B C3B N2B . . 108.1(18) ?
N1B C3B Se1B . . 125.1(18) ?
N2B C3B Se1B . . 127(3) ?
N1B C4B H4BA . . 109.5 ?
N1B C4B H4BB . . 109.5 ?
H4BA C4B H4BB . . 109.5 ?
N1B C4B H4BC . . 109.5 ?
H4BA C4B H4BC . . 109.5 ?
H4BB C4B H4BC . . 109.5 ?
N1B C5B C10B . . 97(5) ?
N1B C5B C6B . . 141(6) ?
C10B C5B C6B . . 122(2) ?
C7B C6B C5B . . 114(3) ?
C7B C6B H6B . . 122.9 ?
C5B C6B H6B . . 122.9 ?
C6B C7B C8B . . 123(3) ?
C6B C7B H7B . . 118.3 ?
C8B C7B H7B . . 118.3 ?
C9B C8B C7B . . 120(2) ?
C9B C8B H8B . . 119.8 ?
C7B C8B H8B . . 119.8 ?
C10B C9B C8B . . 117(2) ?
C10B C9B H9B . . 121.4 ?
C8B C9B H9B . . 121.4 ?
C9B C10B C5B . . 121(3) ?
C9B C10B N2B . . 122(6) ?
C5B C10B N2B . . 116(6) ?
Se2 C2A H2AA . . 109.5 ?
Se2 C2A H2AB . . 109.5 ?
H2AA C2A H2AB . . 109.5 ?
Se2 C2A H2AC . . 109.5 ?
H2AA C2A H2AC . . 109.5 ?
H2AB C2A H2AC . . 109.5 ?
C11 N3 C18 . . 108.9(3) ?
C11 N3 C23 . . 125.6(3) ?
C18 N3 C23 . . 125.0(3) ?
C11 N4 C13 . . 109.2(3) ?
C11 N4 C12 . . 126.8(3) ?
C13 N4 C12 . . 123.8(3) ?
C11 Se2 C2A . . 94.86(17) ?
N4 C11 N3 . . 108.8(3) ?
N4 C11 Se2 . . 126.9(3) ?
N3 C11 Se2 . . 124.2(3) ?
N4 C12 H12A . . 109.5 ?
N4 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
N4 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
N4 C13 C18 . . 106.6(3) ?
N4 C13 C14 . . 131.5(4) ?
C18 C13 C14 . . 121.9(4) ?
C15 C14 C13 . . 116.3(4) ?
C15 C14 H14 . . 121.9 ?
C13 C14 H14 . . 121.9 ?
C14 C15 C16 . . 122.1(4) ?
C14 C15 H15 . . 119.0 ?
C16 C15 H15 . . 119.0 ?
C17 C16 C15 . . 121.8(4) ?
C17 C16 H16 . . 119.1 ?
C15 C16 H16 . . 119.1 ?
C16 C17 C18 . . 115.7(4) ?
C16 C17 H17 . . 122.1 ?
C18 C17 H17 . . 122.1 ?
N3 C18 C13 . . 106.5(3) ?
N3 C18 C17 . . 131.3(3) ?
C13 C18 C17 . . 122.2(3) ?
C20 C19 C24 . . 122.5(3) ?
C20 C19 N2A . . 118.9(5) ?
C24 C19 N2A . . 118.6(5) ?
C20 C19 N2B . . 121(9) ?
C24 C19 N2B . . 115(8) ?
C19 C20 C21 . . 118.7(3) ?
C19 C20 H20 . . 120.7 ?
C21 C20 H20 . . 120.7 ?
C22 C21 C20 . . 120.5(3) ?
C22 C21 H21 . . 119.7 ?
C20 C21 H21 . . 119.7 ?
C21 C22 C23 . . 119.1(3) ?
C21 C22 H22 . . 120.5 ?
C23 C22 H22 . . 120.5 ?
C24 C23 C22 . . 121.9(3) ?
C24 C23 N3 . . 119.7(3) ?
C22 C23 N3 . . 118.4(3) ?
C19 C24 C23 . . 117.3(3) ?
C19 C24 H24 . . 121.3 ?
C23 C24 H24 . . 121.3 ?
O2 S1 O3 . . 115.94(19) ?
O2 S1 O1 . . 114.8(2) ?
O3 S1 O1 . . 114.0(2) ?
O2 S1 C25 . . 103.0(2) ?
O3 S1 C25 . . 104.2(2) ?
O1 S1 C25 . . 102.5(3) ?
F3 C25 F1 . . 108.3(5) ?
F3 C25 F2 . . 108.6(5) ?
F1 C25 F2 . . 106.9(5) ?
F3 C25 S1 . . 110.9(4) ?
F1 C25 S1 . . 111.3(4) ?
F2 C25 S1 . . 110.7(4) ?
F4 C26 F5 . . 104.9(5) ?
F4 C26 F6 . . 109.4(5) ?
F5 C26 F6 . . 107.1(4) ?
F4 C26 S2A . . 105.8(4) ?
F5 C26 S2A . . 116.0(4) ?
F6 C26 S2A . . 113.2(5) ?
F4 C26 S2B . . 119.5(4) ?
F5 C26 S2B . . 105.5(4) ?
F6 C26 S2B . . 109.7(4) ?
C27A C27A Cl1A 2_655 . 107.9(10) ?
C27A C27A H27A 2_655 . 110.1 ?
Cl1A C27A H27A . . 110.1 ?
C27A C27A H27B 2_655 . 110.1 ?
Cl1A C27A H27B . . 110.1 ?
H27A C27A H27B . . 108.4 ?
C27B C27B Cl1B 2_655 . 108.7(15) ?
C27B C27B H27C 2_655 . 110.0 ?
Cl1B C27B H27C . . 110.0 ?
C27B C27B H27D 2_655 . 110.0 ?
Cl1B C27B H27D . . 110.0 ?
H27C C27B H27D . . 108.3 ?
O4A S2A O5A . . 119.3(5) ?
O4A S2A O6A . . 108.6(5) ?
O5A S2A O6A . . 116.4(7) ?
O4A S2A C26 . . 107.6(5) ?
O5A S2A C26 . . 100.8(5) ?
O6A S2A C26 . . 102.0(5) ?
O5B S2B O6B . . 115.3(6) ?
O5B S2B O4B . . 113.1(5) ?
O6B S2B O4B . . 118.8(5) ?
O5B S2B C26 . . 107.5(5) ?
O6B S2B C26 . . 99.5(5) ?
O4B S2B C26 . . 99.5(4) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Se1A C3A . 1.891(4) ?
Se1A C1A . 1.946(4) ?
N1A C3A . 1.338(5) ?
N1A C5A . 1.386(5) ?
N1A C4A . 1.461(5) ?
N2A C3A . 1.339(5) ?
N2A C10A . 1.397(6) ?
N2A C19 . 1.439(4) ?
C1A H1AA . 0.9800 ?
C1A H1AB . 0.9800 ?
C1A H1AC . 0.9800 ?
C4A H4AA . 0.9800 ?
C4A H4AB . 0.9800 ?
C4A H4AC . 0.9800 ?
C5A C10A . 1.382(6) ?
C5A C6A . 1.404(6) ?
C6A C7A . 1.380(7) ?
C6A H6A . 0.9500 ?
C7A C8A . 1.393(8) ?
C7A H7A . 0.9500 ?
C8A C9A . 1.376(7) ?
C8A H8A . 0.9500 ?
C9A C10A . 1.391(7) ?
C9A H9A . 0.9500 ?
Se1B C3B . 1.89(2) ?
Se1B C1B . 1.94(2) ?
C1B H1BA . 0.9800 ?
C1B H1BB . 0.9800 ?
C1B H1BC . 0.9800 ?
N1B C3B . 1.337(19) ?
N1B C5B . 1.38(2) ?
N1B C4B . 1.455(18) ?
N2B C3B . 1.35(2) ?
N2B C10B . 1.40(2) ?
N2B C19 . 1.446(16) ?
C4B H4BA . 0.9800 ?
C4B H4BB . 0.9800 ?
C4B H4BC . 0.9800 ?
C5B C10B . 1.38(2) ?
C5B C6B . 1.41(2) ?
C6B C7B . 1.37(2) ?
C6B H6B . 0.9500 ?
C7B C8B . 1.40(2) ?
C7B H7B . 0.9500 ?
C8B C9B . 1.38(2) ?
C8B H8B . 0.9500 ?
C9B C10B . 1.38(2) ?
C9B H9B . 0.9500 ?
C2A Se2 . 1.961(4) ?
C2A H2AA . 0.9800 ?
C2A H2AB . 0.9800 ?
C2A H2AC . 0.9800 ?
N3 C11 . 1.352(5) ?
N3 C18 . 1.388(5) ?
N3 C23 . 1.444(5) ?
N4 C11 . 1.331(5) ?
N4 C13 . 1.391(5) ?
N4 C12 . 1.468(5) ?
Se2 C11 . 1.899(4) ?
C12 H12A . 0.9800 ?
C12 H12B . 0.9800 ?
C12 H12C . 0.9800 ?
C13 C18 . 1.392(5) ?
C13 C14 . 1.393(5) ?
C14 C15 . 1.376(7) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.405(7) ?
C15 H15 . 0.9500 ?
C16 C17 . 1.391(6) ?
C16 H16 . 0.9500 ?
C17 C18 . 1.392(6) ?
C17 H17 . 0.9500 ?
C19 C20 . 1.382(5) ?
C19 C24 . 1.386(5) ?
C20 C21 . 1.389(5) ?
C20 H20 . 0.9500 ?
C21 C22 . 1.386(6) ?
C21 H21 . 0.9500 ?
C22 C23 . 1.387(5) ?
C22 H22 . 0.9500 ?
C23 C24 . 1.387(5) ?
C24 H24 . 0.9500 ?
S1 O2 . 1.437(3) ?
S1 O3 . 1.437(3) ?
S1 O1 . 1.439(3) ?
S1 C25 . 1.821(5) ?
F1 C25 . 1.323(6) ?
F2 C25 . 1.328(6) ?
F3 C25 . 1.310(7) ?
F4 C26 . 1.301(6) ?
F5 C26 . 1.322(6) ?
F6 C26 . 1.333(6) ?
C26 S2A . 1.794(9) ?
C26 S2B . 1.850(8) ?
Cl1A C27A . 1.78(2) ?
C27A C27A 2_655 1.499(18) ?
C27A H27A . 0.9900 ?
C27A H27B . 0.9900 ?
Cl1B C27B . 1.81(3) ?
C27B C27B 2_655 1.52(3) ?
C27B H27C . 0.9900 ?
C27B H27D . 0.9900 ?
S2A O4A . 1.372(8) ?
S2A O5A . 1.415(8) ?
S2A O6A . 1.441(9) ?
S2B O5B . 1.430(8) ?
S2B O6B . 1.451(8) ?
S2B O4B . 1.500(7) ?
