#------------------------------------------------------------------------------ #$Date: 2021-06-05 22:21:39 +0300 (Sat, 05 Jun 2021) $ #$Revision: 266140 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/06/06/7060611.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_7060611 loop_ _publ_author_name 'Le Gal, Yann' 'Roisnel, Thierry' 'Barri\`ere, Fr\'ed\'eric' 'Mori, Takehiko' 'Lorcy, Dominique' _publ_section_title ; Diselenolene proligands: reactivity and comparison with their dithiolene congeners ; _journal_issue 20 _journal_name_full 'New Journal of Chemistry' _journal_page_first 8971 _journal_page_last 8977 _journal_paper_doi 10.1039/D1NJ01335A _journal_volume 45 _journal_year 2021 _chemical_compound_source 'synthesis as described' _chemical_formula_moiety 'C10 H10 N2 S4 Se2' _chemical_formula_sum 'C10 H10 N2 S4 Se2' _chemical_formula_weight 444.36 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _atom_sites_solution_secondary difmap _audit_update_record ; 2021-02-16 deposited with the CCDC. 2021-04-26 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 99.984(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 7.9196(7) _cell_length_b 8.7472(7) _cell_length_c 20.8069(19) _cell_measurement_reflns_used 9914 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 27.5619 _cell_measurement_theta_min 2.5317 _cell_measurement_wavelength 0.710730 _cell_volume 1419.6(2) _computing_cell_refinement 'APEX3 (Bruker, 2015)' _computing_data_collection 'Bruker APEX3 (Bruker, 2015)' _computing_data_reduction 'SAINT (Bruker, 2014)' _computing_molecular_graphics ; 'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2016)' ; _computing_publication_material 'CRYSCALC (T. Roisnel, local program, 2019)' _computing_structure_refinement 'SHELXL-2018_3 (Sheldrick, 2018)' _computing_structure_solution 'SHELXT 2018_2 (Sheldrick, 2018)' _diffrn_ambient_temperature 150(2) _diffrn_detector '(CMOS) PHOTON 100' _diffrn_detector_area_resol_mean 10.4167 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_device_type 'D8 VENTURE Bruker AXS' _diffrn_measurement_method 'rotation images' _diffrn_orient_matrix_UB_11 0.0249491 _diffrn_orient_matrix_UB_12 0.0506747 _diffrn_orient_matrix_UB_13 0.0437004 _diffrn_orient_matrix_UB_21 0.1214802 _diffrn_orient_matrix_UB_22 -0.0360899 _diffrn_orient_matrix_UB_23 0.0055754 _diffrn_orient_matrix_UB_31 0.0325291 _diffrn_orient_matrix_UB_32 0.0959118 _diffrn_orient_matrix_UB_33 -0.0209910 _diffrn_radiation_monochromator 'multilayer monochromator' _diffrn_radiation_probe x-ray _diffrn_radiation_source 'Incoatec microfocus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0396 _diffrn_reflns_av_unetI/netI 0.0355 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_number 13819 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.533 _diffrn_reflns_theta_min 2.532 _diffrn_source_current 1.00 _diffrn_source_power 50.0 _diffrn_source_voltage 50.00 _exptl_absorpt_coefficient_mu 5.779 _exptl_absorpt_correction_T_max 0.728 _exptl_absorpt_correction_T_min 0.479 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA] ; _exptl_crystal_colour black _exptl_crystal_density_diffrn 2.079 _exptl_crystal_description prism _exptl_crystal_F_000 864 _exptl_crystal_size_max 0.310 _exptl_crystal_size_mid 0.120 _exptl_crystal_size_min 0.055 _refine_diff_density_max 0.659 _refine_diff_density_min -0.759 _refine_diff_density_rms 0.095 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 165 _refine_ls_number_reflns 3262 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.026 _refine_ls_R_factor_all 0.0283 _refine_ls_R_factor_gt 0.0238 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0216P)^2^+1.3917P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0558 _refine_ls_wR_factor_ref 0.0579 _reflns_number_gt 2975 _reflns_number_total 3262 _reflns_threshold_expression >2sigma(I) _cod_data_source_file d1nj01335a2.cif _cod_data_source_block compound7 _cod_depositor_comments 'Adding full bibliography for 7060610--7060611.cif.' _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 7060611 _shelx_res_file ; TITL Y883 [Space group= P2(1)/n] job.res created by SHELXL-2018/3 at 13:30:44 on 01-Jul-2020 CELL 0.71073 7.9196 8.7472 20.8069 90.000 99.984 90.000 ZERR 4.00 0.0007 0.0007 0.0019 0.000 0.003 0.000 LATT 1 SYMM 1/2 - X, 1/2 + Y, 1/2 - Z SFAC C H N S SE UNIT 40 40 8 16 8 MERG 2 FMAP 2 PLAN 20 SIZE 0.05 0.12 0.31 ACTA BOND $H CONF LIST 4 WPDB -2 L.S. 4 TEMP -123.00 WGHT 0.021600 1.391700 FVAR 0.37025 SE1 5 0.135779 0.524924 0.582917 11.00000 0.01284 0.02048 = 0.01491 0.00352 -0.00063 -0.00261 SE2 5 0.166075 0.789503 0.565280 11.00000 0.01435 0.02020 = 0.02371 0.00735 0.00694 0.00568 S1 4 0.579380 0.356895 0.814340 11.00000 0.02224 0.01916 = 0.01168 0.00544 0.00233 0.00164 S2 4 0.645901 0.561547 0.706912 11.00000 0.01238 0.01731 = 0.01126 0.00295 0.00114 -0.00087 S3 4 0.695599 0.674287 0.547588 11.00000 0.01300 0.01805 = 0.01248 0.00411 0.00487 0.00225 S4 4 0.711975 0.847859 0.424503 11.00000 0.02802 0.01626 = 0.01434 0.00227 0.01168 -0.00054 C1 1 0.513206 0.441936 0.742563 11.00000 0.01508 0.01123 = 0.01076 -0.00070 0.00426 0.00080 N2 3 0.355836 0.434494 0.703979 11.00000 0.01476 0.01165 = 0.01173 -0.00003 0.00473 0.00020 C3 1 0.214427 0.346007 0.723374 11.00000 0.01585 0.01413 = 0.01534 0.00157 0.00499 -0.00363 AFIX 23 H3A 2 0.262787 0.260779 0.752090 11.00000 -1.20000 H3B 2 0.143730 0.301311 0.683946 11.00000 -1.20000 AFIX 0 C4 1 0.101941 0.442678 0.758653 11.00000 0.01789 0.02005 = 0.02406 0.00077 0.01031 -0.00087 AFIX 137 H4A 2 0.170277 0.483530 0.798761 11.00000 -1.50000 H4B 2 0.008484 0.379909 0.769654 11.00000 -1.50000 H4C 2 0.053962 0.527417 0.730470 11.00000 -1.50000 AFIX 0 C5 1 0.341157 0.517190 0.646391 11.00000 0.01524 0.01516 = 0.00883 -0.00178 0.00222 0.00376 C6 1 0.486200 0.591294 0.638864 11.00000 0.01333 0.01520 = 0.00793 0.00080 0.00013 0.00322 C7 1 0.509946 0.678118 0.581146 11.00000 0.01281 0.01454 = 0.01058 0.00106 0.00530 -0.00039 C8 1 0.386289 0.759531 0.542727 11.00000 0.01344 0.01334 = 0.01276 0.00043 0.00365 -0.00002 N9 3 0.438707 0.817989 0.486850 11.00000 0.01634 0.01259 = 0.00895 0.00217 0.00174 0.00071 C10 1 0.603903 0.787170 0.482007 11.00000 0.01971 0.00951 = 0.01088 0.00001 0.00394 0.00071 C11 1 0.319854 0.891897 0.433242 11.00000 0.02221 0.01421 = 0.01295 0.00400 -0.00217 0.00284 AFIX 23 H11A 2 0.383035 0.967537 0.411109 11.00000 -1.20000 H11B 2 0.228956 0.946611 0.451197 11.00000 -1.20000 AFIX 0 C12 1 0.239090 0.772175 0.384307 11.00000 0.04121 0.02009 = 0.02392 0.00056 -0.01406 -0.00397 AFIX 137 H12A 2 0.329224 0.719289 0.366121 11.00000 -1.50000 H12B 2 0.160278 0.822142 0.349034 11.00000 -1.50000 H12C 2 0.175768 0.698010 0.406259 11.00000 -1.50000 AFIX 0 HKLF 4 REM Y883 [Space group= P2(1)/n] REM wR2 = 0.0579, GooF = S = 1.026, Restrained GooF = 1.026 for all data REM R1 = 0.0238 for 2975 Fo > 4sig(Fo) and 0.0283 for all 3262 data REM 165 parameters refined using 0 restraints END WGHT 0.0186 1.3991 REM Highest difference peak 0.659, deepest hole -0.759, 1-sigma level 0.095 Q1 1 0.0382 0.8566 0.4275 11.00000 0.05 0.66 Q2 1 0.2774 0.7136 0.5607 11.00000 0.05 0.61 Q3 1 0.1264 0.7433 0.5323 11.00000 0.05 0.59 Q4 1 0.4304 0.9009 0.3942 11.00000 0.05 0.41 Q5 1 0.3789 0.8561 0.4587 11.00000 0.05 0.38 Q6 1 0.3995 0.5756 0.6399 11.00000 0.05 0.37 Q7 1 0.5487 0.5714 0.6624 11.00000 0.05 0.37 Q8 1 0.4992 0.6343 0.6081 11.00000 0.05 0.36 Q9 1 0.3146 0.3845 0.7085 11.00000 0.05 0.35 Q10 1 0.0228 0.5166 0.5890 11.00000 0.05 0.35 Q11 1 0.5808 0.6558 0.5636 11.00000 0.05 0.34 Q12 1 0.5930 0.8295 0.4162 11.00000 0.05 0.34 Q13 1 0.4269 0.6810 0.5573 11.00000 0.05 0.34 Q14 1 0.4459 0.3418 0.7841 11.00000 0.05 0.34 Q15 1 0.8368 0.8368 0.4355 11.00000 0.05 0.34 Q16 1 0.6547 0.7432 0.5125 11.00000 0.05 0.33 Q17 1 0.5248 0.8260 0.4866 11.00000 0.05 0.33 Q18 1 0.3554 0.4684 0.6724 11.00000 0.05 0.33 Q19 1 0.5246 0.4415 0.7745 11.00000 0.05 0.31 Q20 1 0.2823 0.7781 0.6103 11.00000 0.05 0.30 ; _shelx_res_checksum 45304 loop_ _space_group_symop_operation_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_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 Se1 Se 0.13578(3) 0.52492(3) 0.58292(2) 0.01644(7) Uani 1 1 d . . . . . Se2 Se 0.16607(3) 0.78950(3) 0.56528(2) 0.01899(7) Uani 1 1 d . . . . . S1 S 0.57938(8) 0.35689(7) 0.81434(3) 0.01777(13) Uani 1 1 d . . . . . S2 S 0.64590(7) 0.56155(6) 0.70691(3) 0.01376(12) Uani 1 1 d . . . . . S3 S 0.69560(7) 0.67429(6) 0.54759(3) 0.01419(12) Uani 1 1 d . . . . . S4 S 0.71197(8) 0.84786(6) 0.42450(3) 0.01859(13) Uani 1 1 d . . . . . C1 C 0.5132(3) 0.4419(2) 0.74256(10) 0.0121(4) Uani 1 1 d . . . . . N2 N 0.3558(2) 0.4345(2) 0.70398(9) 0.0124(4) Uani 1 1 d . . . . . C3 C 0.2144(3) 0.3460(2) 0.72337(11) 0.0148(4) Uani 1 1 d . . . . . H3A H 0.262787 0.260779 0.752090 0.018 Uiso 1 1 calc R U . . . H3B H 0.143730 0.301311 0.683946 0.018 Uiso 1 1 calc R U . . . C4 C 0.1019(3) 0.4427(3) 0.75865(12) 0.0199(5) Uani 1 1 d . . . . . H4A H 0.170277 0.483530 0.798761 0.030 Uiso 1 1 calc R U . . . H4B H 0.008484 0.379909 0.769654 0.030 Uiso 1 1 calc R U . . . H4C H 0.053962 0.527417 0.730470 0.030 Uiso 1 1 calc R U . . . C5 C 0.3412(3) 0.5172(2) 0.64639(10) 0.0131(4) Uani 1 1 d . . . . . C6 C 0.4862(3) 0.5913(3) 0.63886(10) 0.0124(4) Uani 1 1 d . . . . . C7 C 0.5099(3) 0.6781(2) 0.58115(10) 0.0123(4) Uani 1 1 d . . . . . C8 C 0.3863(3) 0.7595(2) 0.54273(11) 0.0130(4) Uani 1 1 d . . . . . N9 N 0.4387(2) 0.8180(2) 0.48685(9) 0.0127(4) Uani 1 1 d . . . . . C10 C 0.6039(3) 0.7872(2) 0.48201(11) 0.0132(4) Uani 1 1 d . . . . . C11 C 0.3199(3) 0.8919(3) 0.43324(11) 0.0171(5) Uani 1 1 d . . . . . H11A H 0.383035 0.967537 0.411109 0.020 Uiso 1 1 calc R U . . . H11B H 0.228956 0.946611 0.451197 0.020 Uiso 1 1 calc R U . . . C12 C 0.2391(4) 0.7722(3) 0.38431(13) 0.0308(7) Uani 1 1 d . . . . . H12A H 0.329224 0.719289 0.366121 0.046 Uiso 1 1 calc R U . . . H12B H 0.160278 0.822142 0.349034 0.046 Uiso 1 1 calc R U . . . H12C H 0.175768 0.698010 0.406259 0.046 Uiso 1 1 calc R U . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Se1 0.01284(12) 0.02048(13) 0.01491(12) 0.00352(8) -0.00063(9) -0.00261(8) Se2 0.01435(12) 0.02020(13) 0.02371(13) 0.00735(9) 0.00694(10) 0.00568(9) S1 0.0222(3) 0.0192(3) 0.0117(3) 0.0054(2) 0.0023(2) 0.0016(2) S2 0.0124(3) 0.0173(3) 0.0113(2) 0.00295(19) 0.0011(2) -0.0009(2) S3 0.0130(3) 0.0181(3) 0.0125(2) 0.0041(2) 0.0049(2) 0.0023(2) S4 0.0280(3) 0.0163(3) 0.0143(3) 0.0023(2) 0.0117(2) -0.0005(2) C1 0.0151(11) 0.0112(10) 0.0108(10) -0.0007(8) 0.0043(8) 0.0008(8) N2 0.0148(9) 0.0116(9) 0.0117(9) 0.0000(7) 0.0047(7) 0.0002(7) C3 0.0159(11) 0.0141(11) 0.0153(10) 0.0016(8) 0.0050(9) -0.0036(8) C4 0.0179(12) 0.0200(12) 0.0241(12) 0.0008(9) 0.0103(10) -0.0009(9) C5 0.0152(11) 0.0152(10) 0.0088(10) -0.0018(8) 0.0022(8) 0.0038(8) C6 0.0133(11) 0.0152(10) 0.0079(9) 0.0008(8) 0.0001(8) 0.0032(8) C7 0.0128(11) 0.0145(10) 0.0106(10) 0.0011(8) 0.0053(8) -0.0004(8) C8 0.0134(11) 0.0133(10) 0.0128(10) 0.0004(8) 0.0036(8) 0.0000(8) N9 0.0163(10) 0.0126(8) 0.0089(8) 0.0022(7) 0.0017(7) 0.0007(7) C10 0.0197(11) 0.0095(10) 0.0109(10) 0.0000(7) 0.0039(9) 0.0007(8) C11 0.0222(12) 0.0142(11) 0.0130(10) 0.0040(8) -0.0022(9) 0.0028(9) C12 0.0412(17) 0.0201(13) 0.0239(13) 0.0006(10) -0.0141(12) -0.0040(11) 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Se Se -0.0929 2.2259 '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 C5 Se1 Se2 92.57(7) . . ? C8 Se2 Se1 91.46(7) . . ? C1 S2 C6 91.67(11) . . ? C7 S3 C10 92.13(11) . . ? N2 C1 S1 128.26(17) . . ? N2 C1 S2 109.66(15) . . ? S1 C1 S2 122.07(13) . . ? C1 N2 C5 114.54(19) . . ? C1 N2 C3 121.65(18) . . ? C5 N2 C3 123.81(19) . . ? N2 C3 C4 112.32(18) . . ? N2 C3 H3A 109.1 . . ? C4 C3 H3A 109.1 . . ? N2 C3 H3B 109.1 . . ? C4 C3 H3B 109.1 . . ? H3A C3 H3B 107.9 . . ? C3 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C3 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C6 C5 N2 113.9(2) . . ? C6 C5 Se1 122.81(17) . . ? N2 C5 Se1 123.33(17) . . ? C5 C6 C7 125.3(2) . . ? C5 C6 S2 110.19(16) . . ? C7 C6 S2 124.45(17) . . ? C8 C7 C6 125.2(2) . . ? C8 C7 S3 110.45(16) . . ? C6 C7 S3 124.07(17) . . ? C7 C8 N9 113.3(2) . . ? C7 C8 Se2 121.82(17) . . ? N9 C8 Se2 124.92(16) . . ? C10 N9 C8 114.74(18) . . ? C10 N9 C11 121.81(19) . . ? C8 N9 C11 123.1(2) . . ? N9 C10 S4 127.55(17) . . ? N9 C10 S3 109.37(16) . . ? S4 C10 S3 123.07(14) . . ? N9 C11 C12 110.04(19) . . ? N9 C11 H11A 109.7 . . ? C12 C11 H11A 109.7 . . ? N9 C11 H11B 109.7 . . ? C12 C11 H11B 109.7 . . ? H11A C11 H11B 108.2 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? 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 Se1 C5 1.910(2) . ? Se1 Se2 2.3620(4) . ? Se2 C8 1.901(2) . ? S1 C1 1.669(2) . ? S2 C1 1.738(2) . ? S2 C6 1.747(2) . ? S3 C7 1.734(2) . ? S3 C10 1.738(2) . ? S4 C10 1.674(2) . ? C1 N2 1.362(3) . ? N2 C5 1.387(3) . ? N2 C3 1.474(3) . ? C3 C4 1.508(3) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 C6 1.351(3) . ? C6 C7 1.460(3) . ? C7 C8 1.354(3) . ? C8 N9 1.397(3) . ? N9 C10 1.357(3) . ? N9 C11 1.478(3) . ? C11 C12 1.522(3) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 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 _geom_torsion_publ_flag C6 S2 C1 N2 -2.41(16) . . . . ? C6 S2 C1 S1 178.75(15) . . . . ? S1 C1 N2 C5 -179.27(17) . . . . ? S2 C1 N2 C5 2.0(2) . . . . ? S1 C1 N2 C3 1.3(3) . . . . ? S2 C1 N2 C3 -177.48(16) . . . . ? C1 N2 C3 C4 93.2(2) . . . . ? C5 N2 C3 C4 -86.2(3) . . . . ? C1 N2 C5 C6 -0.2(3) . . . . ? C3 N2 C5 C6 179.2(2) . . . . ? C1 N2 C5 Se1 179.29(15) . . . . ? C3 N2 C5 Se1 -1.3(3) . . . . ? N2 C5 C6 C7 175.7(2) . . . . ? Se1 C5 C6 C7 -3.8(3) . . . . ? N2 C5 C6 S2 -1.6(2) . . . . ? Se1 C5 C6 S2 178.85(11) . . . . ? C1 S2 C6 C5 2.31(18) . . . . ? C1 S2 C6 C7 -175.09(19) . . . . ? C5 C6 C7 C8 33.8(4) . . . . ? S2 C6 C7 C8 -149.2(2) . . . . ? C5 C6 C7 S3 -139.1(2) . . . . ? S2 C6 C7 S3 37.9(3) . . . . ? C10 S3 C7 C8 1.05(18) . . . . ? C10 S3 C7 C6 174.84(19) . . . . ? C6 C7 C8 N9 -173.5(2) . . . . ? S3 C7 C8 N9 0.2(2) . . . . ? C6 C7 C8 Se2 7.1(3) . . . . ? S3 C7 C8 Se2 -179.21(11) . . . . ? C7 C8 N9 C10 -1.9(3) . . . . ? Se2 C8 N9 C10 177.52(16) . . . . ? C7 C8 N9 C11 171.3(2) . . . . ? Se2 C8 N9 C11 -9.3(3) . . . . ? C8 N9 C10 S4 -175.96(17) . . . . ? C11 N9 C10 S4 10.8(3) . . . . ? C8 N9 C10 S3 2.6(2) . . . . ? C11 N9 C10 S3 -170.65(16) . . . . ? C7 S3 C10 N9 -2.06(17) . . . . ? C7 S3 C10 S4 176.58(15) . . . . ? C10 N9 C11 C12 85.1(3) . . . . ? C8 N9 C11 C12 -87.6(3) . . . . ?