# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Santos, Paulo' _publ_contact_author_email psantos@utad.pt _publ_section_title ; Crystal Structures of a Benzoselenazole-Derived Squarylium Cyanine Dye and Three Derivatives Substituted at the Central Squaric Ring ; _publ_author_name P.Santos #========================================================== # END of CIF #========================================================== data_5 _database_code_depnum_ccdc_archive 'CCDC 751392' #TrackingRef '- RSC Article.cif.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3-Hexyl-2-[3-(3-hexyl-3H-benzoselenazol-2-ylidenemethyl)-2-methoxy-4- oxocyclobut-2-enylidenemethyl]benzoselenazol-3-ium trifluoromethanesulfonate ; _chemical_name_common ; 3-Hexyl-2-(3-(3-hexyl-3H-benzoselenazol-2-ylidenemethyl)-2- methoxy-4-oxocyclobut-2-enylidenemethyl)benzoselenazol-3-ium trifluoromethanesulfonate ; _chemical_melting_point ? _chemical_formula_moiety 'C33 H39 N2 O2 Se2, C F3 O3 S' _chemical_formula_sum 'C34 H39 F3 N2 O5 S Se2' _chemical_formula_weight 802.65 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' 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' Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.1131(18) _cell_length_b 25.500(5) _cell_length_c 14.645(3) _cell_angle_alpha 90.00 _cell_angle_beta 98.376(2) _cell_angle_gamma 90.00 _cell_volume 3367.0(12) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 2451 _cell_measurement_theta_min 4.98 _cell_measurement_theta_max 26.16 _exptl_crystal_description plate _exptl_crystal_colour black _exptl_crystal_size_max 0.05 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.583 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1632 _exptl_absorpt_coefficient_mu 2.319 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.893 _exptl_absorpt_correction_T_max 0.977 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; Absolute Tmin and Tmax unknown, but SADABS gives ratio as 0.325. ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.78480 _diffrn_radiation_type synchrotron _diffrn_radiation_source 'Daresbury SRS station 16.2smx' _diffrn_radiation_monochromator 'silicon 111' _diffrn_measurement_device_type 'Bruker SMART APEX2 CCD diffractometer' _diffrn_measurement_method 'fine-slice \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 5 _diffrn_reflns_number 18494 _diffrn_reflns_av_R_equivalents 0.0891 _diffrn_reflns_av_sigmaI/netI 0.1032 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 4.70 _diffrn_reflns_theta_max 27.85 _reflns_number_total 5881 _reflns_number_gt 3682 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution SHELXS97 _computing_structure_refinement SHELXL97 _computing_molecular_graphics ? _computing_publication_material SHELXL97 _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.1005P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0114(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5881 _refine_ls_number_parameters 428 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1123 _refine_ls_R_factor_gt 0.0612 _refine_ls_wR_factor_ref 0.1683 _refine_ls_wR_factor_gt 0.1412 _refine_ls_goodness_of_fit_ref 0.955 _refine_ls_restrained_S_all 0.955 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 Se2 Se -0.06116(7) 0.25750(3) 0.60195(5) 0.0260(2) Uani 1 1 d . . . Se1 Se 0.25632(7) 0.29937(3) 0.28462(5) 0.0258(2) Uani 1 1 d . . . O1 O 0.1032(5) 0.25961(18) 0.4428(3) 0.0297(11) Uani 1 1 d . . . O2 O 0.1503(5) 0.08554(17) 0.3836(3) 0.0271(11) Uani 1 1 d . . . N1 N 0.3407(6) 0.2323(2) 0.1598(4) 0.0239(13) Uani 1 1 d . . . N2 N -0.1481(5) 0.1665(2) 0.6719(4) 0.0236(13) Uani 1 1 d . . . C1 C 0.1229(8) 0.0457(3) 0.4517(5) 0.0308(17) Uani 1 1 d . . . H11 H 0.1630 0.0578 0.5138 0.038 Uiso 1 1 calc R . . H12 H 0.1716 0.0128 0.4387 0.038 Uiso 1 1 calc R . . H13 H 0.0159 0.0398 0.4480 0.038 Uiso 1 1 calc R . . C2 C 0.2791(7) 0.2310(3) 0.2389(5) 0.0250(16) Uani 1 1 d . . . C3 C 0.3771(7) 0.3748(3) 0.1614(5) 0.0270(16) Uani 1 1 d . . . H3 H 0.3505 0.4033 0.1975 0.034 Uiso 1 1 calc R . . C4 C 0.4479(7) 0.3832(3) 0.0843(5) 0.0296(17) Uani 1 1 d . . . H4 H 0.4680 0.4180 0.0666 0.037 Uiso 1 1 calc R . . C5 C 0.4888(8) 0.3417(3) 0.0335(5) 0.0360(18) Uani 1 1 d . . . H5 H 0.5400 0.3484 -0.0174 0.045 Uiso 1 1 calc R . . C6 C 0.4572(7) 0.2906(3) 0.0548(5) 0.0268(16) Uani 1 1 d . . . H6 H 0.4849 0.2622 0.0188 0.033 Uiso 1 1 calc R . . C7 C 0.3834(7) 0.2816(3) 0.1306(5) 0.0256(16) Uani 1 1 d . . . C8 C 0.3472(7) 0.3234(3) 0.1835(5) 0.0248(15) Uani 1 1 d . . . C9 C 0.2388(7) 0.1848(3) 0.2793(4) 0.0243(15) Uani 1 1 d . . . H9 H 0.2613 0.1531 0.2500 0.030 Uiso 1 1 calc R . . C10 C 0.1695(7) 0.1794(3) 0.3575(4) 0.0218(15) Uani 1 1 d . . . C11 C 0.1273(7) 0.1349(3) 0.4042(5) 0.0230(15) Uani 1 1 d . . . C12 C 0.0623(7) 0.1634(3) 0.4711(5) 0.0245(15) Uani 1 1 d . . . C13 C 0.1094(6) 0.2121(3) 0.4278(5) 0.0244(16) Uani 1 1 d . . . C14 C -0.0152(7) 0.1493(3) 0.5427(5) 0.0238(15) Uani 1 1 d . . . H14 H -0.0299 0.1129 0.5516 0.030 Uiso 1 1 calc R . . C15 C -0.0737(7) 0.1839(3) 0.6032(5) 0.0253(15) Uani 1 1 d . . . C16 C -0.1851(7) 0.2988(3) 0.7625(5) 0.0296(16) Uani 1 1 d . . . H16 H -0.1599 0.3334 0.7468 0.037 Uiso 1 1 calc R . . C17 C -0.2557(7) 0.2898(3) 0.8382(5) 0.0288(17) Uani 1 1 d . . . H17 H -0.2791 0.3183 0.8751 0.036 Uiso 1 1 calc R . . C18 C -0.2931(7) 0.2381(3) 0.8607(5) 0.0341(18) Uani 1 1 d . . . H18 H -0.3424 0.2325 0.9126 0.043 Uiso 1 1 calc R . . C19 C -0.2599(7) 0.1959(3) 0.8093(5) 0.0303(17) Uani 1 1 d . . . H19 H -0.2841 0.1613 0.8257 0.038 Uiso 1 1 calc R . . C20 C -0.1896(7) 0.2051(3) 0.7322(4) 0.0230(15) Uani 1 1 d . . . C21 C -0.1515(7) 0.2563(3) 0.7095(5) 0.0255(16) Uani 1 1 d . . . C22 C 0.3532(7) 0.1845(3) 0.1023(5) 0.0277(16) Uani 1 1 d . . . H221 H 0.3436 0.1947 0.0365 0.035 Uiso 1 1 calc R . . H222 H 0.2710 0.1602 0.1095 0.035 Uiso 1 1 calc R . . C23 C 0.5005(7) 0.1564(3) 0.1296(5) 0.0299(16) Uani 1 1 d . . . H231 H 0.5114 0.1468 0.1958 0.037 Uiso 1 1 calc R . . H232 H 0.5828 0.1804 0.1209 0.037 Uiso 1 1 calc R . . C24 C 0.5104(8) 0.1071(3) 0.0722(5) 0.0287(16) Uani 1 1 d . . . H241 H 0.5917 0.0848 0.1031 0.036 Uiso 1 1 calc R . . H242 H 0.4167 0.0872 0.0699 0.036 Uiso 1 1 calc R . . C25 C 0.5377(7) 0.1180(3) -0.0259(5) 0.0276(16) Uani 1 1 d . . . H251 H 0.6400 0.1316 -0.0238 0.035 Uiso 1 1 calc R . . H252 H 0.4689 0.1460 -0.0522 0.035 Uiso 1 1 calc R . . C26 C 0.5183(8) 0.0705(3) -0.0912(5) 0.0352(18) Uani 1 1 d . . . H261 H 0.5490 0.0805 -0.1509 0.044 Uiso 1 1 calc R . . H262 H 0.5844 0.0419 -0.0644 0.044 Uiso 1 1 calc R . . C27 C 0.3596(8) 0.0503(3) -0.1083(5) 0.042(2) Uani 1 1 d . . . H271 H 0.3321 0.0367 -0.0505 0.053 Uiso 1 1 calc R . . H272 H 0.3518 0.0221 -0.1544 0.053 Uiso 1 1 calc R . . H273 H 0.2926 0.0790 -0.1311 0.053 Uiso 1 1 calc R . . C28 C -0.1803(7) 0.1105(3) 0.6871(5) 0.0266(16) Uani 1 1 d . . . H281 H -0.1932 0.0922 0.6269 0.033 Uiso 1 1 calc R . . H282 H -0.2753 0.1080 0.7121 0.033 Uiso 1 1 calc R . . C29 C -0.0608(7) 0.0824(3) 0.7526(5) 0.0289(16) Uani 1 1 d . . . H291 H -0.0306 0.1044 0.8077 0.036 Uiso 1 1 calc R . . H292 H 0.0273 0.0766 0.7215 0.036 Uiso 1 1 calc R . . C30 C -0.1181(7) 0.0296(3) 0.7823(5) 0.0292(17) Uani 1 1 d . . . H301 H -0.2035 0.0360 0.8155 0.037 Uiso 1 1 calc R . . H302 H -0.1546 0.0090 0.7263 0.037 Uiso 1 1 calc R . . C31 C -0.0044(7) -0.0029(3) 0.8436(5) 0.0295(16) Uani 1 1 d . . . H311 H 0.0354 0.0180 0.8985 0.037 Uiso 1 1 calc R . . H312 H 0.0789 -0.0111 0.8095 0.037 Uiso 1 1 calc R . . C32 C -0.0678(8) -0.0540(3) 0.8750(5) 0.0344(18) Uani 1 1 d . . . H321 H -0.1128 -0.0739 0.8200 0.043 Uiso 1 1 calc R . . H322 H -0.1475 -0.0457 0.9120 0.043 Uiso 1 1 calc R . . C33 C 0.0485(9) -0.0886(3) 0.9328(6) 0.045(2) Uani 1 1 d . . . H331 H 0.1248 -0.0987 0.8954 0.056 Uiso 1 1 calc R . . H332 H 0.0005 -0.1201 0.9527 0.056 Uiso 1 1 calc R . . H333 H 0.0946 -0.0690 0.9870 0.056 Uiso 1 1 calc R . . S3 S 0.71505(18) 0.04650(7) 0.35382(12) 0.0272(4) Uani 1 1 d . . . F1 F 0.4585(4) 0.01378(17) 0.3957(3) 0.0448(12) Uani 1 1 d . . . F2 F 0.4542(4) 0.09076(17) 0.3357(3) 0.0439(11) Uani 1 1 d . . . F3 F 0.4636(4) 0.0230(2) 0.2501(3) 0.0525(13) Uani 1 1 d . . . O3 O 0.7603(5) -0.00745(17) 0.3457(3) 0.0309(11) Uani 1 1 d . . . O4 O 0.7494(5) 0.0804(2) 0.2821(4) 0.0418(14) Uani 1 1 d . . . O5 O 0.7422(6) 0.0678(2) 0.4460(4) 0.0460(14) Uani 1 1 d . . . C34 C 0.5133(7) 0.0429(3) 0.3318(5) 0.0289(16) Uani 1 1 d . . . 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 Se2 0.0289(4) 0.0291(4) 0.0222(4) -0.0003(3) 0.0109(3) 0.0000(3) Se1 0.0289(4) 0.0272(4) 0.0236(4) -0.0015(3) 0.0118(3) 0.0008(3) O1 0.036(3) 0.024(3) 0.031(3) -0.002(2) 0.012(2) -0.001(2) O2 0.033(3) 0.024(3) 0.028(3) 0.004(2) 0.017(2) 0.002(2) N1 0.025(3) 0.023(3) 0.026(3) 0.000(2) 0.014(2) 0.001(2) N2 0.022(3) 0.027(3) 0.025(3) -0.003(3) 0.012(2) -0.003(2) C1 0.036(4) 0.034(4) 0.026(4) 0.006(3) 0.017(3) 0.002(3) C2 0.018(3) 0.038(4) 0.022(4) -0.003(3) 0.012(3) 0.004(3) C3 0.027(4) 0.025(4) 0.028(4) 0.003(3) 0.003(3) 0.004(3) C4 0.032(4) 0.033(4) 0.024(4) 0.010(3) 0.004(3) -0.006(3) C5 0.035(4) 0.040(5) 0.035(5) 0.011(4) 0.012(3) -0.004(3) C6 0.030(4) 0.030(4) 0.025(4) 0.001(3) 0.019(3) 0.001(3) C7 0.024(3) 0.028(4) 0.027(4) 0.004(3) 0.012(3) 0.003(3) C8 0.021(3) 0.032(4) 0.022(4) 0.003(3) 0.004(3) 0.001(3) C9 0.029(4) 0.026(4) 0.021(4) 0.001(3) 0.014(3) 0.002(3) C10 0.021(3) 0.027(4) 0.019(4) -0.003(3) 0.006(3) -0.001(3) C11 0.014(3) 0.032(4) 0.023(4) -0.006(3) 0.003(3) 0.001(3) C12 0.019(3) 0.030(4) 0.025(4) -0.001(3) 0.005(3) -0.005(3) C13 0.014(3) 0.035(4) 0.026(4) 0.000(3) 0.006(3) 0.000(3) C14 0.021(3) 0.024(4) 0.030(4) -0.003(3) 0.013(3) -0.003(3) C15 0.026(4) 0.031(4) 0.020(4) 0.000(3) 0.008(3) -0.004(3) C16 0.029(4) 0.034(4) 0.026(4) 0.005(3) 0.004(3) 0.003(3) C17 0.021(3) 0.043(5) 0.024(4) -0.008(3) 0.006(3) 0.004(3) C18 0.027(4) 0.046(5) 0.032(5) -0.007(4) 0.010(3) -0.002(3) C19 0.024(4) 0.036(4) 0.033(4) 0.001(3) 0.010(3) -0.004(3) C20 0.025(3) 0.033(4) 0.013(3) 0.000(3) 0.011(3) 0.001(3) C21 0.024(3) 0.032(4) 0.021(4) -0.003(3) 0.007(3) 0.000(3) C22 0.025(4) 0.032(4) 0.028(4) 0.000(3) 0.011(3) -0.003(3) C23 0.028(4) 0.038(4) 0.025(4) -0.002(3) 0.010(3) 0.002(3) C24 0.033(4) 0.033(4) 0.024(4) 0.004(3) 0.015(3) 0.004(3) C25 0.026(4) 0.034(4) 0.025(4) 0.002(3) 0.008(3) 0.001(3) C26 0.037(4) 0.051(5) 0.022(4) -0.007(4) 0.018(3) 0.003(4) C27 0.038(4) 0.055(5) 0.037(5) -0.012(4) 0.017(4) -0.011(4) C28 0.027(4) 0.030(4) 0.025(4) -0.007(3) 0.013(3) -0.006(3) C29 0.028(4) 0.030(4) 0.031(4) -0.003(3) 0.014(3) -0.002(3) C30 0.028(4) 0.032(4) 0.030(4) -0.003(3) 0.010(3) -0.009(3) C31 0.023(3) 0.033(4) 0.034(4) 0.000(3) 0.009(3) -0.004(3) C32 0.033(4) 0.034(4) 0.037(5) 0.001(4) 0.004(3) -0.001(3) C33 0.051(5) 0.037(5) 0.047(5) 0.009(4) 0.008(4) 0.003(4) S3 0.0251(9) 0.0282(10) 0.0290(11) 0.0001(8) 0.0065(7) 0.0005(7) F1 0.040(2) 0.047(3) 0.054(3) 0.013(2) 0.026(2) 0.004(2) F2 0.037(2) 0.045(3) 0.053(3) 0.007(2) 0.014(2) 0.014(2) F3 0.033(2) 0.084(4) 0.039(3) -0.021(3) 0.002(2) -0.009(2) O3 0.036(3) 0.025(3) 0.033(3) 0.000(2) 0.012(2) 0.004(2) O4 0.035(3) 0.040(3) 0.054(4) 0.015(3) 0.019(3) 0.002(2) O5 0.043(3) 0.054(4) 0.038(3) -0.016(3) -0.003(2) 0.005(3) C34 0.031(4) 0.026(4) 0.033(4) 0.001(3) 0.015(3) 0.003(3) 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 Se2 C15 1.881(7) . ? Se2 C21 1.881(7) . ? Se1 C2 1.890(7) . ? Se1 C8 1.901(7) . ? O1 C13 1.234(8) . ? O2 C11 1.317(8) . ? O2 C1 1.470(8) . ? N1 C2 1.359(8) . ? N1 C7 1.403(8) . ? N1 C22 1.494(8) . ? N2 C15 1.366(8) . ? N2 C20 1.410(8) . ? N2 C28 1.482(8) . ? C1 H11 0.98 . ? C1 H12 0.98 . ? C1 H13 0.98 . ? C2 C9 1.391(9) . ? C3 C8 1.386(9) . ? C3 C4 1.397(9) . ? C3 H3 0.95 . ? C4 C5 1.376(10) . ? C4 H4 0.95 . ? C5 C6 1.382(10) . ? C5 H5 0.95 . ? C6 C7 1.398(9) . ? C6 H6 0.95 . ? C7 C8 1.386(9) . ? C9 C10 1.393(9) . ? C9 H9 0.95 . ? C10 C11 1.408(9) . ? C10 C13 1.490(9) . ? C11 C12 1.417(9) . ? C11 C13 2.011(10) . ? C12 C14 1.395(9) . ? C12 C13 1.486(9) . ? C14 C15 1.408(9) . ? C14 H14 0.95 . ? C16 C17 1.379(10) . ? C16 C21 1.391(9) . ? C16 H16 0.95 . ? C17 C18 1.411(10) . ? C17 H17 0.95 . ? C18 C19 1.372(10) . ? C18 H18 0.95 . ? C19 C20 1.396(9) . ? C19 H19 0.95 . ? C20 C21 1.404(9) . ? C22 C23 1.523(9) . ? C22 H221 0.99 . ? C22 H222 0.99 . ? C23 C24 1.522(9) . ? C23 H231 0.99 . ? C23 H232 0.99 . ? C24 C25 1.519(9) . ? C24 H241 0.99 . ? C24 H242 0.99 . ? C25 C26 1.538(9) . ? C25 H251 0.99 . ? C25 H252 0.99 . ? C26 C27 1.521(9) . ? C26 H261 0.99 . ? C26 H262 0.99 . ? C27 H271 0.98 . ? C27 H272 0.98 . ? C27 H273 0.98 . ? C28 C29 1.522(9) . ? C28 H281 0.99 . ? C28 H282 0.99 . ? C29 C30 1.530(9) . ? C29 H291 0.99 . ? C29 H292 0.99 . ? C30 C31 1.514(10) . ? C30 H301 0.99 . ? C30 H302 0.99 . ? C31 C32 1.523(9) . ? C31 H311 0.99 . ? C31 H312 0.99 . ? C32 C33 1.535(10) . ? C32 H321 0.99 . ? C32 H322 0.99 . ? C33 H331 0.98 . ? C33 H332 0.98 . ? C33 H333 0.98 . ? S3 O4 1.430(5) . ? S3 O5 1.442(5) . ? S3 O3 1.446(5) . ? S3 C34 1.823(7) . ? F1 C34 1.346(8) . ? F2 C34 1.338(8) . ? F3 C34 1.318(8) . ? 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 C15 Se2 C21 86.7(3) . . ? C2 Se1 C8 86.5(3) . . ? C11 O2 C1 117.2(5) . . ? C2 N1 C7 116.7(6) . . ? C2 N1 C22 122.4(6) . . ? C7 N1 C22 120.8(5) . . ? C15 N2 C20 116.3(5) . . ? C15 N2 C28 123.6(5) . . ? C20 N2 C28 120.1(5) . . ? O2 C1 H11 109.5 . . ? O2 C1 H12 109.5 . . ? H11 C1 H12 109.5 . . ? O2 C1 H13 109.5 . . ? H11 C1 H13 109.5 . . ? H12 C1 H13 109.5 . . ? N1 C2 C9 123.4(6) . . ? N1 C2 Se1 111.1(5) . . ? C9 C2 Se1 125.5(5) . . ? C8 C3 C4 117.6(7) . . ? C8 C3 H3 121.2 . . ? C4 C3 H3 121.2 . . ? C5 C4 C3 120.9(7) . . ? C5 C4 H4 119.6 . . ? C3 C4 H4 119.6 . . ? C4 C5 C6 121.5(7) . . ? C4 C5 H5 119.3 . . ? C6 C5 H5 119.3 . . ? C5 C6 C7 118.3(7) . . ? C5 C6 H6 120.9 . . ? C7 C6 H6 120.9 . . ? C8 C7 C6 120.0(6) . . ? C8 C7 N1 114.9(6) . . ? C6 C7 N1 125.1(6) . . ? C7 C8 C3 121.7(6) . . ? C7 C8 Se1 110.7(5) . . ? C3 C8 Se1 127.6(5) . . ? C10 C9 C2 127.8(6) . . ? C10 C9 H9 116.1 . . ? C2 C9 H9 116.1 . . ? C9 C10 C11 131.9(6) . . ? C9 C10 C13 140.3(6) . . ? C11 C10 C13 87.8(5) . . ? O2 C11 C10 126.6(6) . . ? O2 C11 C12 138.1(6) . . ? C10 C11 C12 95.3(5) . . ? O2 C11 C13 174.0(5) . . ? C10 C11 C13 47.8(4) . . ? C12 C11 C13 47.6(4) . . ? C14 C12 C11 134.1(6) . . ? C14 C12 C13 138.2(6) . . ? C11 C12 C13 87.6(5) . . ? O1 C13 C12 136.1(6) . . ? O1 C13 C10 134.7(6) . . ? C12 C13 C10 89.1(5) . . ? O1 C13 C11 178.0(5) . . ? C12 C14 C15 126.3(6) . . ? C12 C14 H14 116.8 . . ? C15 C14 H14 116.8 . . ? N2 C15 C14 122.4(6) . . ? N2 C15 Se2 111.5(5) . . ? C14 C15 Se2 126.1(5) . . ? C17 C16 C21 119.0(7) . . ? C17 C16 H16 120.5 . . ? C21 C16 H16 120.5 . . ? C16 C17 C18 119.9(7) . . ? C16 C17 H17 120.0 . . ? C18 C17 H17 120.0 . . ? C19 C18 C17 121.6(7) . . ? C19 C18 H18 119.2 . . ? C17 C18 H18 119.2 . . ? C18 C19 C20 118.4(7) . . ? C18 C19 H19 120.8 . . ? C20 C19 H19 120.8 . . ? C21 C20 C19 120.4(6) . . ? C21 C20 N2 113.8(5) . . ? C19 C20 N2 125.9(6) . . ? C16 C21 C20 120.6(6) . . ? C16 C21 Se2 127.9(5) . . ? C20 C21 Se2 111.5(5) . . ? N1 C22 C23 111.9(5) . . ? N1 C22 H221 109.2 . . ? C23 C22 H221 109.2 . . ? N1 C22 H222 109.2 . . ? C23 C22 H222 109.2 . . ? H221 C22 H222 107.9 . . ? C22 C23 C24 111.3(6) . . ? C22 C23 H231 109.4 . . ? C24 C23 H231 109.4 . . ? C22 C23 H232 109.4 . . ? C24 C23 H232 109.4 . . ? H231 C23 H232 108.0 . . ? C25 C24 C23 113.7(6) . . ? C25 C24 H241 108.8 . . ? C23 C24 H241 108.8 . . ? C25 C24 H242 108.8 . . ? C23 C24 H242 108.8 . . ? H241 C24 H242 107.7 . . ? C24 C25 C26 115.1(6) . . ? C24 C25 H251 108.5 . . ? C26 C25 H251 108.5 . . ? C24 C25 H252 108.5 . . ? C26 C25 H252 108.5 . . ? H251 C25 H252 107.5 . . ? C27 C26 C25 113.0(6) . . ? C27 C26 H261 109.0 . . ? C25 C26 H261 109.0 . . ? C27 C26 H262 109.0 . . ? C25 C26 H262 109.0 . . ? H261 C26 H262 107.8 . . ? C26 C27 H271 109.5 . . ? C26 C27 H272 109.5 . . ? H271 C27 H272 109.5 . . ? C26 C27 H273 109.5 . . ? H271 C27 H273 109.5 . . ? H272 C27 H273 109.5 . . ? N2 C28 C29 114.2(5) . . ? N2 C28 H281 108.7 . . ? C29 C28 H281 108.7 . . ? N2 C28 H282 108.7 . . ? C29 C28 H282 108.7 . . ? H281 C28 H282 107.6 . . ? C28 C29 C30 110.6(5) . . ? C28 C29 H291 109.5 . . ? C30 C29 H291 109.5 . . ? C28 C29 H292 109.5 . . ? C30 C29 H292 109.5 . . ? H291 C29 H292 108.1 . . ? C31 C30 C29 114.7(5) . . ? C31 C30 H301 108.6 . . ? C29 C30 H301 108.6 . . ? C31 C30 H302 108.6 . . ? C29 C30 H302 108.6 . . ? H301 C30 H302 107.6 . . ? C30 C31 C32 113.0(5) . . ? C30 C31 H311 109.0 . . ? C32 C31 H311 109.0 . . ? C30 C31 H312 109.0 . . ? C32 C31 H312 109.0 . . ? H311 C31 H312 107.8 . . ? C31 C32 C33 113.4(6) . . ? C31 C32 H321 108.9 . . ? C33 C32 H321 108.9 . . ? C31 C32 H322 108.9 . . ? C33 C32 H322 108.9 . . ? H321 C32 H322 107.7 . . ? C32 C33 H331 109.5 . . ? C32 C33 H332 109.5 . . ? H331 C33 H332 109.5 . . ? C32 C33 H333 109.5 . . ? H331 C33 H333 109.5 . . ? H332 C33 H333 109.5 . . ? O4 S3 O5 115.8(3) . . ? O4 S3 O3 114.8(3) . . ? O5 S3 O3 115.0(3) . . ? O4 S3 C34 102.9(3) . . ? O5 S3 C34 102.4(3) . . ? O3 S3 C34 103.3(3) . . ? F3 C34 F2 107.7(6) . . ? F3 C34 F1 107.8(6) . . ? F2 C34 F1 106.4(5) . . ? F3 C34 S3 112.6(5) . . ? F2 C34 S3 110.4(5) . . ? F1 C34 S3 111.8(5) . . ? 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 C7 N1 C2 C9 -176.3(6) . . . . ? C22 N1 C2 C9 8.0(10) . . . . ? C7 N1 C2 Se1 3.8(7) . . . . ? C22 N1 C2 Se1 -171.9(5) . . . . ? C8 Se1 C2 N1 -1.8(5) . . . . ? C8 Se1 C2 C9 178.3(6) . . . . ? C8 C3 C4 C5 -1.3(10) . . . . ? C3 C4 C5 C6 2.3(11) . . . . ? C4 C5 C6 C7 -0.8(11) . . . . ? C5 C6 C7 C8 -1.6(10) . . . . ? C5 C6 C7 N1 178.6(6) . . . . ? C2 N1 C7 C8 -4.3(8) . . . . ? C22 N1 C7 C8 171.5(6) . . . . ? C2 N1 C7 C6 175.6(6) . . . . ? C22 N1 C7 C6 -8.7(10) . . . . ? C6 C7 C8 C3 2.5(10) . . . . ? N1 C7 C8 C3 -177.6(6) . . . . ? C6 C7 C8 Se1 -177.3(5) . . . . ? N1 C7 C8 Se1 2.5(7) . . . . ? C4 C3 C8 C7 -1.1(10) . . . . ? C4 C3 C8 Se1 178.8(5) . . . . ? C2 Se1 C8 C7 -0.4(5) . . . . ? C2 Se1 C8 C3 179.8(6) . . . . ? N1 C2 C9 C10 -177.0(6) . . . . ? Se1 C2 C9 C10 2.9(10) . . . . ? C2 C9 C10 C11 -178.6(6) . . . . ? C2 C9 C10 C13 0.7(13) . . . . ? C1 O2 C11 C10 168.5(6) . . . . ? C1 O2 C11 C12 -10.8(11) . . . . ? C9 C10 C11 O2 2.3(11) . . . . ? C13 C10 C11 O2 -177.2(6) . . . . ? C9 C10 C11 C12 -178.1(7) . . . . ? C13 C10 C11 C12 2.4(5) . . . . ? C9 C10 C11 C13 179.5(9) . . . . ? O2 C11 C12 C14 -4.7(14) . . . . ? C10 C11 C12 C14 175.8(7) . . . . ? C13 C11 C12 C14 178.1(10) . . . . ? O2 C11 C12 C13 177.1(8) . . . . ? C10 C11 C12 C13 -2.4(5) . . . . ? C14 C12 C13 O1 4.5(14) . . . . ? C11 C12 C13 O1 -177.5(8) . . . . ? C14 C12 C13 C10 -175.8(8) . . . . ? C11 C12 C13 C10 2.2(5) . . . . ? C14 C12 C13 C11 -178.0(11) . . . . ? C9 C10 C13 O1 -2.0(14) . . . . ? C11 C10 C13 O1 177.5(8) . . . . ? C9 C10 C13 C12 178.3(8) . . . . ? C11 C10 C13 C12 -2.2(5) . . . . ? C9 C10 C13 C11 -179.4(11) . . . . ? C10 C11 C13 C12 176.8(7) . . . . ? C12 C11 C13 C10 -176.8(7) . . . . ? C11 C12 C14 C15 -179.5(7) . . . . ? C13 C12 C14 C15 -2.3(13) . . . . ? C20 N2 C15 C14 174.7(6) . . . . ? C28 N2 C15 C14 -2.8(10) . . . . ? C20 N2 C15 Se2 -5.0(7) . . . . ? C28 N2 C15 Se2 177.4(4) . . . . ? C12 C14 C15 N2 -179.8(6) . . . . ? C12 C14 C15 Se2 -0.1(10) . . . . ? C21 Se2 C15 N2 4.8(5) . . . . ? C21 Se2 C15 C14 -175.0(6) . . . . ? C21 C16 C17 C18 -0.2(10) . . . . ? C16 C17 C18 C19 0.5(10) . . . . ? C17 C18 C19 C20 -1.1(10) . . . . ? C18 C19 C20 C21 1.3(10) . . . . ? C18 C19 C20 N2 -179.8(6) . . . . ? C15 N2 C20 C21 2.1(8) . . . . ? C28 N2 C20 C21 179.8(6) . . . . ? C15 N2 C20 C19 -176.9(6) . . . . ? C28 N2 C20 C19 0.7(10) . . . . ? C17 C16 C21 C20 0.4(10) . . . . ? C17 C16 C21 Se2 178.2(5) . . . . ? C19 C20 C21 C16 -1.0(10) . . . . ? N2 C20 C21 C16 179.9(6) . . . . ? C19 C20 C21 Se2 -179.1(5) . . . . ? N2 C20 C21 Se2 1.8(7) . . . . ? C15 Se2 C21 C16 178.4(6) . . . . ? C15 Se2 C21 C20 -3.7(5) . . . . ? C2 N1 C22 C23 -91.7(7) . . . . ? C7 N1 C22 C23 92.7(7) . . . . ? N1 C22 C23 C24 178.6(5) . . . . ? C22 C23 C24 C25 75.0(7) . . . . ? C23 C24 C25 C26 -168.7(6) . . . . ? C24 C25 C26 C27 64.9(8) . . . . ? C15 N2 C28 C29 90.3(8) . . . . ? C20 N2 C28 C29 -87.2(7) . . . . ? N2 C28 C29 C30 166.5(5) . . . . ? C28 C29 C30 C31 176.8(6) . . . . ? C29 C30 C31 C32 177.4(6) . . . . ? C30 C31 C32 C33 176.8(6) . . . . ? O4 S3 C34 F3 61.0(6) . . . . ? O5 S3 C34 F3 -178.6(5) . . . . ? O3 S3 C34 F3 -58.8(6) . . . . ? O4 S3 C34 F2 -59.4(5) . . . . ? O5 S3 C34 F2 61.1(6) . . . . ? O3 S3 C34 F2 -179.1(5) . . . . ? O4 S3 C34 F1 -177.6(5) . . . . ? O5 S3 C34 F1 -57.1(5) . . . . ? O3 S3 C34 F1 62.7(5) . . . . ? _geom_special_details ; Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) 7.3635 (0.0147) x - 1.5808 (0.0674) y + 6.7652 (0.0353) z = 3.2750 (0.0234) * 0.0015 (0.0045) C3 * -0.0128 (0.0048) C4 * 0.0107 (0.0049) C5 * 0.0026 (0.0048) C6 * -0.0138 (0.0047) C7 * 0.0118 (0.0045) C8 Rms deviation of fitted atoms = 0.0102 7.3410 (0.0223) x - 0.4216 (0.1076) y + 6.8633 (0.0533) z = 3.6362 (0.0276) Angle to previous plane (with approximate esd) = 2.63 ( 0.49 ) * -0.0145 (0.0031) C10 * 0.0153 (0.0033) C11 * -0.0145 (0.0031) C12 * 0.0137 (0.0030) C13 Rms deviation of fitted atoms = 0.0145 7.4013 (0.0146) x - 2.4244 (0.0627) y + 6.6077 (0.0359) z = 2.9434 (0.0353) Angle to previous plane (with approximate esd) = 4.62 ( 0.49 ) * 0.0003 (0.0047) C16 * 0.0000 (0.0046) C17 * -0.0029 (0.0048) C18 * 0.0056 (0.0048) C19 * -0.0053 (0.0046) C20 * 0.0024 (0.0047) C21 Rms deviation of fitted atoms = 0.0035 7.3635 (0.0147) x - 1.5808 (0.0674) y + 6.7652 (0.0353) z = 3.2750 (0.0234) Angle to previous plane (with approximate esd) = 2.00 ( 0.39 ) * 0.0015 (0.0045) C3 * -0.0128 (0.0048) C4 * 0.0107 (0.0049) C5 * 0.0026 (0.0048) C6 * -0.0138 (0.0047) C7 * 0.0118 (0.0045) C8 Rms deviation of fitted atoms = 0.0102 ; _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.85 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.948 _refine_diff_density_min -0.925 _refine_diff_density_rms 0.184 # Attachment '- RSC Article.cif.txt' data_4 _database_code_depnum_ccdc_archive 'CCDC 751393' #TrackingRef '- RSC Article.cif.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-[(3-hexylbenzoselenazol-3-ium-2-yl)methylidene]-2-[(3-hexyl-3H- benzoselenazol-2-ylidene)methyl]-3-oxocyclobut-1-en-1-olate ; _chemical_name_common ; 4-((3-hexylbenzoselenazol-3-ium-2-yl)methylidene)-2-((3-hexyl- 3H-benzoselenazol-2-ylidene)methyl)-3-oxocyclobut-1-en-1-olate ; _chemical_melting_point ? _chemical_formula_moiety 'C32 H36 N2 O2 Se2' _chemical_formula_sum 'C32 H36 N2 O2 Se2' _chemical_formula_weight 638.54 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' Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' 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' _cell_length_a 11.0233(11) _cell_length_b 9.7399(9) _cell_length_c 13.1575(13) _cell_angle_alpha 90.00 _cell_angle_beta 98.227(5) _cell_angle_gamma 90.00 _cell_volume 1398.1(2) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 3297 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Plate _exptl_crystal_colour Purple _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.517 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 652 _exptl_absorpt_coefficient_mu 2.677 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.739 _exptl_absorpt_correction_T_max 0.948 _exptl_absorpt_process_details '(SADABS; Sheldrick, 2003)' _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker Nonius FR591 rotating anode' _diffrn_radiation_monochromator '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius 95mm CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16560 _diffrn_reflns_av_R_equivalents 0.0948 _diffrn_reflns_av_sigmaI/netI 0.0727 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.08 _diffrn_reflns_theta_max 26.00 _reflns_number_total 2737 _reflns_number_gt 1855 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'COLLECT (Hooft, 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) and COLLECT' _computing_data_reduction 'DENZO and COLLECT' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material SHELXL97 _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0939P)^2^+2.7106P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2737 _refine_ls_number_parameters 173 _refine_ls_number_restraints 32 _refine_ls_R_factor_all 0.1378 _refine_ls_R_factor_gt 0.0940 _refine_ls_wR_factor_ref 0.2171 _refine_ls_wR_factor_gt 0.1974 _refine_ls_goodness_of_fit_ref 1.159 _refine_ls_restrained_S_all 1.180 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 Se3 Se 0.85715(8) 0.12264(10) 0.01240(6) 0.0648(4) Uani 1 1 d . . . O1 O 0.9624(5) 0.7020(6) 0.0755(4) 0.0647(16) Uani 1 1 d . . . N1 N 0.7041(6) 0.2276(7) 0.1363(4) 0.0526(16) Uani 1 1 d . . . C2 C 0.7966(7) 0.2710(8) 0.0841(5) 0.0477(19) Uani 1 1 d . . . C4 C 0.7130(11) -0.1260(10) 0.0452(7) 0.076(3) Uani 1 1 d . . . H4 H 0.7617 -0.1786 0.0056 0.095 Uiso 1 1 calc R . . C5 C 0.6197(12) -0.1864(11) 0.0871(8) 0.083(3) Uani 1 1 d . . . H5 H 0.6042 -0.2817 0.0771 0.103 Uiso 1 1 calc R . . C6 C 0.5475(9) -0.1094(9) 0.1439(7) 0.069(2) Uani 1 1 d . . . H6 H 0.4809 -0.1523 0.1700 0.086 Uiso 1 1 calc R . . C7 C 0.5704(8) 0.0288(9) 0.1633(6) 0.061(2) Uani 1 1 d . . . H7 H 0.5216 0.0805 0.2034 0.076 Uiso 1 1 calc R . . C8 C 0.6681(7) 0.0902(8) 0.1218(6) 0.0520(19) Uani 1 1 d . . . C9 C 0.7359(8) 0.0137(9) 0.0615(6) 0.060(2) Uani 1 1 d . . . C10 C 0.8384(7) 0.4031(9) 0.0856(5) 0.053(2) Uani 1 1 d . . . H10 H 0.7992 0.4667 0.1249 0.066 Uiso 1 1 calc R . . C11 C 0.9311(6) 0.4550(9) 0.0363(5) 0.0516(19) Uani 1 1 d . . . C12 C 0.9830(6) 0.5925(9) 0.0339(6) 0.0514(19) Uani 1 1 d . . . C13 C 0.6435(6) 0.3179(8) 0.2024(5) 0.0445(16) Uani 1 1 d U . . H131 H 0.7024 0.3886 0.2325 0.056 Uiso 1 1 calc R . . H132 H 0.6187 0.2633 0.2595 0.056 Uiso 1 1 calc R . . C14 C 0.5314(7) 0.3880(7) 0.1447(5) 0.0446(15) Uani 1 1 d U . . H141 H 0.4743 0.3176 0.1114 0.056 Uiso 1 1 calc R . . H142 H 0.5567 0.4470 0.0901 0.056 Uiso 1 1 calc R . . C15 C 0.4653(7) 0.4760(9) 0.2165(6) 0.0573(19) Uani 1 1 d U . . H151 H 0.4460 0.4180 0.2739 0.072 Uiso 1 1 calc R . . H152 H 0.5212 0.5499 0.2461 0.072 Uiso 1 1 calc R . . C16 C 0.3474(9) 0.5403(13) 0.1633(7) 0.092(3) Uani 1 1 d DU . . H161 H 0.3076 0.4736 0.1123 0.115 Uiso 1 1 calc R . . H162 H 0.3696 0.6217 0.1247 0.115 Uiso 1 1 calc R . . C17 C 0.2533(11) 0.5848(15) 0.2304(9) 0.127(4) Uani 1 1 d DU . . H171 H 0.1749 0.6076 0.1872 0.159 Uiso 1 1 calc R . . H172 H 0.2383 0.5096 0.2776 0.159 Uiso 1 1 calc R . . C18 C 0.3023(13) 0.7086(13) 0.2907(12) 0.146(5) Uani 1 1 d DU . . H181 H 0.3734 0.6821 0.3403 0.182 Uiso 1 1 calc R . . H182 H 0.2385 0.7464 0.3275 0.182 Uiso 1 1 calc R . . H183 H 0.3269 0.7781 0.2439 0.182 Uiso 1 1 calc R . . 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 Se3 0.0746(6) 0.0852(7) 0.0364(5) -0.0057(4) 0.0145(4) 0.0331(5) O1 0.060(3) 0.085(4) 0.054(3) -0.014(3) 0.025(3) 0.011(3) N1 0.057(4) 0.074(5) 0.029(3) 0.003(3) 0.013(3) 0.015(3) C2 0.056(4) 0.065(5) 0.023(3) -0.004(3) 0.008(3) 0.025(4) C4 0.109(8) 0.070(6) 0.043(5) -0.011(5) -0.010(5) 0.038(6) C5 0.128(9) 0.060(6) 0.050(6) -0.003(5) -0.019(6) 0.009(6) C6 0.089(6) 0.062(6) 0.050(5) -0.001(4) -0.006(5) 0.004(5) C7 0.083(6) 0.063(6) 0.036(4) 0.009(4) 0.007(4) 0.002(4) C8 0.062(5) 0.059(5) 0.033(4) 0.004(3) 0.000(4) 0.016(4) C9 0.082(6) 0.062(5) 0.035(4) 0.001(4) 0.007(4) 0.021(4) C10 0.043(4) 0.084(6) 0.034(4) -0.009(4) 0.011(3) 0.014(4) C11 0.041(4) 0.084(6) 0.031(4) -0.004(4) 0.008(3) 0.018(4) C12 0.036(4) 0.080(6) 0.038(4) -0.008(4) 0.006(3) 0.009(4) C13 0.053(4) 0.054(4) 0.029(3) -0.004(3) 0.015(3) 0.005(3) C14 0.052(4) 0.051(4) 0.032(3) -0.006(3) 0.012(3) 0.002(3) C15 0.062(4) 0.074(5) 0.038(4) -0.001(3) 0.012(3) 0.014(4) C16 0.086(5) 0.127(6) 0.063(5) -0.009(5) 0.011(4) 0.051(5) C17 0.116(7) 0.170(9) 0.090(7) -0.002(7) -0.003(6) 0.058(7) C18 0.162(12) 0.153(12) 0.134(11) 0.046(10) 0.062(10) 0.050(10) 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 Se3 C9 1.891(9) . ? Se3 C2 1.899(7) . ? O1 C12 1.234(9) . ? N1 C2 1.375(10) . ? N1 C8 1.401(10) . ? N1 C13 1.463(9) . ? C2 C10 1.366(11) . ? C4 C5 1.367(15) . ? C4 C9 1.394(13) . ? C4 H4 0.95 . ? C5 C6 1.388(14) . ? C5 H5 0.95 . ? C6 C7 1.387(12) . ? C6 H6 0.95 . ? C7 C8 1.409(11) . ? C7 H7 0.95 . ? C8 C9 1.384(11) . ? C10 C11 1.382(11) . ? C10 H10 0.95 . ? C11 C12 1.459(11) . ? C11 C12 1.489(10) 3_765 ? C12 C11 1.489(10) 3_765 ? C13 C14 1.517(10) . ? C13 H131 0.99 . ? C13 H132 0.99 . ? C14 C15 1.535(10) . ? C14 H141 0.99 . ? C14 H142 0.99 . ? C15 C16 1.521(12) . ? C15 H151 0.99 . ? C15 H152 0.99 . ? C16 C17 1.518(16) . ? C16 H161 0.99 . ? C16 H162 0.99 . ? C17 C18 1.500(19) . ? C17 H171 0.99 . ? C17 H172 0.99 . ? C18 H181 0.98 . ? C18 H182 0.98 . ? C18 H183 0.98 . ? 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 C9 Se3 C2 86.6(4) . . ? C2 N1 C8 116.2(6) . . ? C2 N1 C13 123.1(7) . . ? C8 N1 C13 120.7(6) . . ? C10 C2 N1 123.8(6) . . ? C10 C2 Se3 125.6(6) . . ? N1 C2 Se3 110.7(6) . . ? C5 C4 C9 119.2(9) . . ? C5 C4 H4 120.4 . . ? C9 C4 H4 120.4 . . ? C4 C5 C6 120.5(9) . . ? C4 C5 H5 119.7 . . ? C6 C5 H5 119.7 . . ? C7 C6 C5 121.3(10) . . ? C7 C6 H6 119.3 . . ? C5 C6 H6 119.3 . . ? C6 C7 C8 118.1(8) . . ? C6 C7 H7 121.0 . . ? C8 C7 H7 121.0 . . ? C9 C8 N1 115.3(7) . . ? C9 C8 C7 119.9(8) . . ? N1 C8 C7 124.8(7) . . ? C8 C9 C4 120.8(9) . . ? C8 C9 Se3 111.1(6) . . ? C4 C9 Se3 128.1(7) . . ? C2 C10 C11 127.5(7) . . ? C2 C10 H10 116.2 . . ? C11 C10 H10 116.2 . . ? C10 C11 C12 131.6(7) . . ? C10 C11 C12 139.2(8) . 3_765 ? C12 C11 C12 89.2(6) . 3_765 ? O1 C12 C11 133.3(7) . . ? O1 C12 C11 135.9(8) . 3_765 ? C11 C12 C11 90.8(6) . 3_765 ? N1 C13 C14 112.5(6) . . ? N1 C13 H131 109.1 . . ? C14 C13 H131 109.1 . . ? N1 C13 H132 109.1 . . ? C14 C13 H132 109.1 . . ? H131 C13 H132 107.8 . . ? C13 C14 C15 111.6(6) . . ? C13 C14 H141 109.3 . . ? C15 C14 H141 109.3 . . ? C13 C14 H142 109.3 . . ? C15 C14 H142 109.3 . . ? H141 C14 H142 108.0 . . ? C16 C15 C14 113.3(7) . . ? C16 C15 H151 108.9 . . ? C14 C15 H151 108.9 . . ? C16 C15 H152 108.9 . . ? C14 C15 H152 108.9 . . ? H151 C15 H152 107.7 . . ? C15 C16 C17 117.3(9) . . ? C15 C16 H161 108.0 . . ? C17 C16 H161 108.0 . . ? C15 C16 H162 108.0 . . ? C17 C16 H162 108.0 . . ? H161 C16 H162 107.2 . . ? C18 C17 C16 108.3(11) . . ? C18 C17 H171 110.0 . . ? C16 C17 H171 110.0 . . ? C18 C17 H172 110.0 . . ? C16 C17 H172 110.0 . . ? H171 C17 H172 108.4 . . ? C17 C18 H181 109.5 . . ? C17 C18 H182 109.5 . . ? H181 C18 H182 109.5 . . ? C17 C18 H183 109.5 . . ? H181 C18 H183 109.5 . . ? H182 C18 H183 109.5 . . ? 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 C8 N1 C2 C10 176.6(7) . . . . ? C13 N1 C2 C10 -2.4(11) . . . . ? C8 N1 C2 Se3 -4.0(7) . . . . ? C13 N1 C2 Se3 177.1(5) . . . . ? C9 Se3 C2 C10 -178.2(7) . . . . ? C9 Se3 C2 N1 2.4(5) . . . . ? C9 C4 C5 C6 0.9(14) . . . . ? C4 C5 C6 C7 -2.5(14) . . . . ? C5 C6 C7 C8 1.3(12) . . . . ? C2 N1 C8 C9 3.9(9) . . . . ? C13 N1 C8 C9 -177.2(7) . . . . ? C2 N1 C8 C7 -175.9(7) . . . . ? C13 N1 C8 C7 3.0(10) . . . . ? C6 C7 C8 C9 1.6(11) . . . . ? C6 C7 C8 N1 -178.6(7) . . . . ? N1 C8 C9 C4 176.9(7) . . . . ? C7 C8 C9 C4 -3.3(12) . . . . ? N1 C8 C9 Se3 -1.8(8) . . . . ? C7 C8 C9 Se3 178.0(6) . . . . ? C5 C4 C9 C8 2.0(13) . . . . ? C5 C4 C9 Se3 -179.5(7) . . . . ? C2 Se3 C9 C8 -0.3(6) . . . . ? C2 Se3 C9 C4 -178.9(8) . . . . ? N1 C2 C10 C11 179.4(7) . . . . ? Se3 C2 C10 C11 0.0(11) . . . . ? C2 C10 C11 C12 -179.2(7) . . . . ? C2 C10 C11 C12 2.2(14) . . . 3_765 ? C10 C11 C12 O1 1.6(14) . . . . ? C12 C11 C12 O1 -179.3(11) 3_765 . . . ? C10 C11 C12 C11 -179.1(10) . . . 3_765 ? C12 C11 C12 C11 0.0 3_765 . . 3_765 ? C2 N1 C13 C14 90.9(8) . . . . ? C8 N1 C13 C14 -88.0(8) . . . . ? N1 C13 C14 C15 176.9(6) . . . . ? C13 C14 C15 C16 -176.0(8) . . . . ? C14 C15 C16 C17 158.7(10) . . . . ? C15 C16 C17 C18 70.9(16) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.066 _refine_diff_density_min -0.905 _refine_diff_density_rms 0.285 #========================================================== # END of CIF #========================================================== data_6 _database_code_depnum_ccdc_archive 'CCDC 751394' #TrackingRef '- RSC Article.cif.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3-Hexyl-2-[3-(3-hexyl-3H-benzoselenazol-2-ylidenemethyl)-2-methylamino-4- oxocyclobut-2-enylidenemethyl]benzoselenazol-3-ium trifluoromethanesulfonate hydrate ; _chemical_name_common ; 3-Hexyl-2-(3-(3-hexyl-3H-benzoselenazol-2-ylidenemethyl)-2- methylamino-4-oxocyclobut-2-enylidenemethyl)benzoselenazol-3-ium trifluoromethanesulfonate hydrate ; _chemical_melting_point ? _chemical_formula_moiety 'C33 H40 N3 O Se2, C F3 O3 S, H2 O' _chemical_formula_sum 'C34 H42 F3 N3 O5 S Se2' _chemical_formula_weight 819.70 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' 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' Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 12.8136(3) _cell_length_b 13.1269(4) _cell_length_c 13.1817(4) _cell_angle_alpha 109.0220(10) _cell_angle_beta 98.479(2) _cell_angle_gamma 116.8880(10) _cell_volume 1751.49(9) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 7828 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Plate _exptl_crystal_colour Blue _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.554 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 836 _exptl_absorpt_coefficient_mu 2.232 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.745 _exptl_absorpt_correction_T_max 0.936 _exptl_absorpt_process_details '(SADABS; Sheldrick, 2003)' _exptl_special_details ; The minimum and maximum absorption values stated above are those calculated in SHELXL97 from the given crystal dimensions. The ratio of minimum to maximum apparent transmission was determined experimentally as 0.860295. ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker Nonius FR591 rotating anode' _diffrn_radiation_monochromator '10 cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius 95mm CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 26283 _diffrn_reflns_av_R_equivalents 0.0535 _diffrn_reflns_av_sigmaI/netI 0.0536 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.00 _diffrn_reflns_theta_max 26.00 _reflns_number_total 6861 _reflns_number_gt 5491 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'COLLECT (Hooft, 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) and COLLECT' _computing_data_reduction 'DENZO and COLLECT' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material SHELXL97 _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+7.7040P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6861 _refine_ls_number_parameters 496 _refine_ls_number_restraints 72 _refine_ls_R_factor_all 0.0740 _refine_ls_R_factor_gt 0.0524 _refine_ls_wR_factor_ref 0.1124 _refine_ls_wR_factor_gt 0.0998 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.081 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 Se1 Se 0.48665(4) 0.15483(4) -0.02814(4) 0.02186(12) Uani 1 1 d . . . Se2 Se -0.05512(4) -0.15465(4) -0.20566(4) 0.02684(13) Uani 1 1 d . . . O1 O 0.2139(3) -0.0040(3) -0.0798(3) 0.0311(8) Uani 1 1 d . . . N1 N 0.6536(3) 0.1970(3) 0.1563(3) 0.0223(8) Uani 1 1 d . . . N2 N -0.2199(3) -0.2610(3) -0.1094(3) 0.0263(8) Uani 1 1 d . . . N3 N 0.2293(3) -0.0499(4) 0.2504(3) 0.0290(9) Uani 1 1 d . . . H31 H 0.3046 -0.0136 0.2992 0.036 Uiso 1 1 calc R . . C1 C 0.1234(5) -0.1183(6) 0.2813(4) 0.0418(13) Uani 1 1 d . . . H11 H 0.0747 -0.0781 0.2867 0.052 Uiso 1 1 calc R . . H12 H 0.1536 -0.1157 0.3554 0.052 Uiso 1 1 calc R . . H13 H 0.0706 -0.2072 0.2227 0.052 Uiso 1 1 calc R . . C2 C 0.5283(4) 0.1437(4) 0.1090(4) 0.0207(9) Uani 1 1 d . . . C3 C 0.7185(4) 0.2894(4) -0.0709(4) 0.0285(10) Uani 1 1 d . . . H3 H 0.6720 0.2797 -0.1403 0.036 Uiso 1 1 calc R . . C4 C 0.8486(4) 0.3521(4) -0.0345(4) 0.0297(11) Uani 1 1 d . . . H4 H 0.8911 0.3852 -0.0803 0.037 Uiso 1 1 calc R . . C5 C 0.9172(4) 0.3672(4) 0.0669(4) 0.0308(11) Uani 1 1 d . . . H5 H 1.0057 0.4119 0.0906 0.038 Uiso 1 1 calc R . . C6 C 0.8570(4) 0.3172(4) 0.1340(4) 0.0270(10) Uani 1 1 d . . . H6 H 0.9037 0.3262 0.2029 0.034 Uiso 1 1 calc R . . C7 C 0.7267(4) 0.2534(4) 0.0988(4) 0.0210(9) Uani 1 1 d . . . C8 C 0.6597(4) 0.2419(4) -0.0023(4) 0.0231(9) Uani 1 1 d . . . C9 C 0.4443(4) 0.0887(4) 0.1594(4) 0.0232(9) Uani 1 1 d . . . H9 H 0.4785 0.0963 0.2324 0.029 Uiso 1 1 calc R . . C10 C 0.3158(4) 0.0242(4) 0.1129(4) 0.0235(9) Uani 1 1 d . . . C11 C 0.2201(4) -0.0387(4) 0.1540(4) 0.0243(10) Uani 1 1 d . . . C12 C 0.1208(4) -0.0822(4) 0.0539(4) 0.0229(9) Uani 1 1 d . . . C13 C 0.2159(4) -0.0171(4) 0.0081(4) 0.0235(10) Uani 1 1 d . . . C14 C -0.0087(4) -0.1563(4) 0.0179(4) 0.0230(9) Uani 1 1 d . . . H14 H -0.0425 -0.1854 0.0695 0.029 Uiso 1 1 calc R . . C15 C -0.0937(4) -0.1926(4) -0.0836(4) 0.0239(10) Uani 1 1 d . . . C16 C -0.2919(5) -0.2596(5) -0.3872(4) 0.0353(12) Uani 1 1 d . . . H16 H -0.2467 -0.2229 -0.4299 0.044 Uiso 1 1 calc R . . C17 C -0.4210(5) -0.3302(5) -0.4276(5) 0.0401(13) Uani 1 1 d . . . H17 H -0.4654 -0.3420 -0.4991 0.050 Uiso 1 1 calc R . . C18 C -0.4864(5) -0.3837(5) -0.3657(5) 0.0374(12) Uani 1 1 d . . . H18 H -0.5751 -0.4337 -0.3965 0.047 Uiso 1 1 calc R . . C19 C -0.4257(4) -0.3661(5) -0.2600(4) 0.0338(12) Uani 1 1 d . . . H19 H -0.4714 -0.4030 -0.2178 0.042 Uiso 1 1 calc R . . C20 C -0.2956(4) -0.2926(4) -0.2168(4) 0.0256(10) Uani 1 1 d . . . C21 C -0.2306(4) -0.2442(4) -0.2826(4) 0.0278(10) Uani 1 1 d . . . C22 C 0.7109(4) 0.1937(4) 0.2596(4) 0.0234(9) Uani 1 1 d . . . H221 H 0.7843 0.1880 0.2535 0.029 Uiso 1 1 calc R . . H222 H 0.6500 0.1166 0.2644 0.029 Uiso 1 1 calc R . . C23 C 0.7516(4) 0.3111(4) 0.3681(4) 0.0253(10) Uani 1 1 d . . . H231 H 0.8042 0.3885 0.3594 0.032 Uiso 1 1 calc R . . H232 H 0.6768 0.3112 0.3792 0.032 Uiso 1 1 calc R . . C24 C 0.8246(4) 0.3158(4) 0.4733(4) 0.0298(11) Uani 1 1 d . . . H241 H 0.8948 0.3077 0.4591 0.037 Uiso 1 1 calc R . . H242 H 0.7693 0.2419 0.4854 0.037 Uiso 1 1 calc R . . C25 C 0.8766(4) 0.4389(5) 0.5828(4) 0.0330(11) Uani 1 1 d . . . H251 H 0.9340 0.4409 0.6437 0.041 Uiso 1 1 calc R . . H252 H 0.9269 0.5123 0.5679 0.041 Uiso 1 1 calc R . . C26 C 0.7819(5) 0.4575(5) 0.6278(4) 0.0416(13) Uani 1 1 d . . . H261 H 0.8255 0.5436 0.6928 0.052 Uiso 1 1 calc R . . H262 H 0.7228 0.4536 0.5669 0.052 Uiso 1 1 calc R . . C27 C 0.7097(7) 0.3610(7) 0.6666(6) 0.081(3) Uani 1 1 d . . . H271 H 0.6553 0.3827 0.7008 0.101 Uiso 1 1 calc R . . H272 H 0.7677 0.3605 0.7236 0.101 Uiso 1 1 calc R . . H273 H 0.6588 0.2764 0.6008 0.101 Uiso 1 1 calc R . . C28 C -0.2753(4) -0.2988(4) -0.0282(4) 0.0271(10) Uani 1 1 d . . . H281 H -0.3539 -0.2999 -0.0386 0.034 Uiso 1 1 calc R . . H282 H -0.2174 -0.2344 0.0508 0.034 Uiso 1 1 calc R . . C29 C -0.3031(4) -0.4304(4) -0.0427(4) 0.0304(11) Uani 1 1 d . . . H291 H -0.3735 -0.4970 -0.1152 0.038 Uiso 1 1 calc R . . H292 H -0.2291 -0.4354 -0.0477 0.038 Uiso 1 1 calc R . . C30 C -0.3360(4) -0.4564(4) 0.0565(4) 0.0306(11) Uani 1 1 d . . . H301 H -0.3869 -0.5497 0.0300 0.038 Uiso 1 1 calc R . . H302 H -0.3878 -0.4217 0.0793 0.038 Uiso 1 1 calc R . . C31 C -0.2215(4) -0.3980(5) 0.1616(4) 0.0318(11) Uani 1 1 d . . . H311 H -0.1696 -0.4324 0.1386 0.040 Uiso 1 1 calc R . . H312 H -0.1709 -0.3046 0.1882 0.040 Uiso 1 1 calc R . . C32 C -0.2535(5) -0.4239(5) 0.2605(5) 0.0354(12) Uani 1 1 d . . . H321 H -0.2975 -0.5169 0.2363 0.044 Uiso 1 1 calc R . . H322 H -0.3112 -0.3962 0.2794 0.044 Uiso 1 1 calc R . . C33 C -0.1396(5) -0.3561(5) 0.3673(5) 0.0434(13) Uani 1 1 d . . . H331 H -0.0973 -0.2638 0.3937 0.054 Uiso 1 1 calc R . . H332 H -0.0821 -0.3835 0.3495 0.054 Uiso 1 1 calc R . . H333 H -0.1657 -0.3775 0.4276 0.054 Uiso 1 1 calc R . . S1 S 0.37647(13) 0.14860(13) 0.65851(12) 0.0375(3) Uani 1 1 d . . . F1 F 0.1550(7) 0.0971(8) 0.5928(8) 0.053(2) Uani 0.50 1 d PU . . F2 F 0.1270(8) 0.0179(11) 0.5479(8) 0.080(3) Uani 0.50 1 d PU . . F3 F 0.1654(8) -0.0595(8) 0.5898(9) 0.069(3) Uani 0.50 1 d PU . . F4 F 0.1832(8) -0.0465(8) 0.6621(9) 0.059(2) Uani 0.50 1 d PU . . F5 F 0.2068(12) 0.0904(13) 0.7491(10) 0.074(3) Uani 0.50 1 d PU . . F6 F 0.1843(11) 0.1212(9) 0.7270(10) 0.061(3) Uani 0.50 1 d PU . . O2 O 0.3747(9) 0.1173(12) 0.5452(8) 0.068(3) Uani 0.50 1 d PU . . O3 O 0.3782(9) 0.0511(10) 0.5679(9) 0.066(3) Uani 0.50 1 d PU . . O4 O 0.4387(7) 0.1024(9) 0.7166(8) 0.049(2) Uani 0.50 1 d PU . . O5 O 0.4418(9) 0.1924(13) 0.7695(9) 0.085(3) Uani 0.50 1 d PU . . O6 O 0.4249(9) 0.2802(9) 0.7264(12) 0.084(3) Uani 0.50 1 d PU . . O7 O 0.3751(10) 0.2412(10) 0.6253(10) 0.067(3) Uani 0.50 1 d PU . . C34 C 0.2172(5) 0.0608(5) 0.6486(4) 0.0344(12) Uani 1 1 d . . . O1W O 0.4812(4) 0.0598(4) 0.3940(3) 0.0441(10) Uani 1 1 d . . . H1W H 0.512(6) 0.014(6) 0.387(5) 0.055 Uiso 1 1 d . . . H2W H 0.468(6) 0.073(6) 0.457(6) 0.055 Uiso 1 1 d . . . 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 0.0181(2) 0.0195(2) 0.0241(2) 0.00878(19) 0.00517(18) 0.00848(18) Se2 0.0242(2) 0.0236(2) 0.0283(3) 0.0102(2) 0.00684(19) 0.0112(2) O1 0.0216(17) 0.0350(19) 0.0325(19) 0.0180(16) 0.0083(14) 0.0104(15) N1 0.0185(18) 0.0189(18) 0.025(2) 0.0083(16) 0.0058(15) 0.0078(15) N2 0.0221(19) 0.0213(19) 0.029(2) 0.0058(17) 0.0063(16) 0.0113(16) N3 0.0213(19) 0.034(2) 0.025(2) 0.0118(18) 0.0074(16) 0.0114(18) C1 0.033(3) 0.061(4) 0.026(3) 0.023(3) 0.013(2) 0.018(3) C2 0.016(2) 0.017(2) 0.022(2) 0.0043(18) 0.0025(17) 0.0083(17) C3 0.031(3) 0.022(2) 0.031(3) 0.010(2) 0.010(2) 0.015(2) C4 0.029(3) 0.024(2) 0.037(3) 0.014(2) 0.018(2) 0.013(2) C5 0.019(2) 0.020(2) 0.047(3) 0.010(2) 0.010(2) 0.0085(19) C6 0.020(2) 0.022(2) 0.030(3) 0.007(2) 0.0034(19) 0.0098(19) C7 0.021(2) 0.017(2) 0.025(2) 0.0074(18) 0.0090(18) 0.0109(18) C8 0.022(2) 0.013(2) 0.027(2) 0.0058(18) 0.0070(19) 0.0067(18) C9 0.019(2) 0.020(2) 0.025(2) 0.0093(19) 0.0047(18) 0.0076(18) C10 0.024(2) 0.019(2) 0.028(2) 0.0080(19) 0.0097(19) 0.0140(19) C11 0.023(2) 0.020(2) 0.026(2) 0.0059(19) 0.0080(19) 0.0117(19) C12 0.021(2) 0.019(2) 0.024(2) 0.0077(19) 0.0071(18) 0.0082(18) C13 0.017(2) 0.019(2) 0.027(2) 0.0065(19) 0.0051(18) 0.0073(18) C14 0.018(2) 0.020(2) 0.026(2) 0.0084(19) 0.0070(18) 0.0081(18) C15 0.020(2) 0.019(2) 0.030(2) 0.0075(19) 0.0078(19) 0.0110(19) C16 0.042(3) 0.025(3) 0.034(3) 0.009(2) 0.004(2) 0.020(2) C17 0.037(3) 0.033(3) 0.037(3) 0.006(2) -0.006(2) 0.020(2) C18 0.028(3) 0.029(3) 0.046(3) 0.007(2) 0.000(2) 0.019(2) C19 0.025(2) 0.028(3) 0.041(3) 0.007(2) 0.008(2) 0.015(2) C20 0.023(2) 0.018(2) 0.031(3) 0.005(2) 0.0046(19) 0.0122(19) C21 0.024(2) 0.019(2) 0.035(3) 0.006(2) 0.002(2) 0.014(2) C22 0.017(2) 0.021(2) 0.028(2) 0.0080(19) 0.0025(18) 0.0107(18) C23 0.023(2) 0.024(2) 0.028(2) 0.009(2) 0.0078(19) 0.013(2) C24 0.025(2) 0.029(3) 0.031(3) 0.008(2) 0.006(2) 0.015(2) C25 0.028(3) 0.031(3) 0.025(3) 0.005(2) 0.004(2) 0.013(2) C26 0.044(3) 0.048(3) 0.025(3) 0.005(2) 0.004(2) 0.028(3) C27 0.067(5) 0.064(5) 0.055(4) 0.006(4) 0.038(4) 0.001(4) C28 0.017(2) 0.028(2) 0.032(3) 0.010(2) 0.0078(19) 0.0107(19) C29 0.022(2) 0.024(2) 0.039(3) 0.010(2) 0.009(2) 0.012(2) C30 0.024(2) 0.022(2) 0.045(3) 0.014(2) 0.012(2) 0.011(2) C31 0.025(2) 0.031(3) 0.045(3) 0.019(2) 0.016(2) 0.015(2) C32 0.033(3) 0.031(3) 0.050(3) 0.020(3) 0.017(2) 0.021(2) C33 0.044(3) 0.046(3) 0.047(3) 0.023(3) 0.011(3) 0.029(3) S1 0.0437(8) 0.0433(8) 0.0367(7) 0.0215(6) 0.0193(6) 0.0275(7) F1 0.036(4) 0.055(4) 0.075(6) 0.036(4) 0.013(4) 0.027(4) F2 0.053(5) 0.114(7) 0.055(5) 0.037(5) 0.006(4) 0.036(5) F3 0.053(4) 0.033(4) 0.099(6) 0.013(5) 0.020(5) 0.019(3) F4 0.054(4) 0.044(4) 0.091(6) 0.036(5) 0.033(5) 0.028(3) F5 0.068(5) 0.115(8) 0.053(5) 0.039(5) 0.036(4) 0.054(5) F6 0.073(6) 0.045(4) 0.071(7) 0.017(4) 0.051(5) 0.036(4) O2 0.056(5) 0.113(7) 0.048(5) 0.048(5) 0.032(4) 0.044(5) O3 0.067(5) 0.067(6) 0.082(6) 0.032(5) 0.050(5) 0.044(5) O4 0.041(4) 0.064(5) 0.060(5) 0.038(4) 0.016(4) 0.034(4) O5 0.045(5) 0.118(8) 0.059(6) 0.052(6) 0.009(4) 0.014(5) O6 0.047(5) 0.043(5) 0.129(8) 0.006(5) 0.019(5) 0.026(4) O7 0.081(6) 0.066(5) 0.091(6) 0.059(5) 0.050(5) 0.044(5) C34 0.052(3) 0.039(3) 0.027(3) 0.019(2) 0.018(2) 0.032(3) O1W 0.047(2) 0.055(3) 0.029(2) 0.016(2) 0.0073(18) 0.029(2) 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 C2 1.879(4) . ? Se1 C8 1.890(4) . ? Se2 C15 1.902(5) . ? Se2 C21 1.904(4) . ? O1 C13 1.224(5) . ? N1 C2 1.365(5) . ? N1 C7 1.395(5) . ? N1 C22 1.471(5) . ? N2 C15 1.365(5) . ? N2 C20 1.401(6) . ? N2 C28 1.465(6) . ? N3 C11 1.321(6) . ? N3 C1 1.454(6) . ? N3 H31 0.88 . ? C1 H11 0.98 . ? C1 H12 0.98 . ? C1 H13 0.98 . ? C2 C9 1.393(6) . ? C3 C8 1.384(6) . ? C3 C4 1.398(6) . ? C3 H3 0.95 . ? C4 C5 1.387(7) . ? C4 H4 0.95 . ? C5 C6 1.388(7) . ? C5 H5 0.95 . ? C6 C7 1.399(6) . ? C6 H6 0.95 . ? C7 C8 1.397(6) . ? C9 C10 1.380(6) . ? C9 H9 0.95 . ? C10 C11 1.432(6) . ? C10 C13 1.484(6) . ? C11 C12 1.429(6) . ? C11 C13 2.029(7) . ? C12 C14 1.391(6) . ? C12 C13 1.480(6) . ? C14 C15 1.374(6) . ? C14 H14 0.95 . ? C16 C21 1.384(7) . ? C16 C17 1.383(7) . ? C16 H16 0.95 . ? C17 C18 1.379(8) . ? C17 H17 0.95 . ? C18 C19 1.381(7) . ? C18 H18 0.95 . ? C19 C20 1.393(6) . ? C19 H19 0.95 . ? C21 C20 1.394(7) . ? C22 C23 1.519(6) . ? C22 H221 0.99 . ? C22 H222 0.99 . ? C23 C24 1.521(6) . ? C23 H231 0.99 . ? C23 H232 0.99 . ? C24 C25 1.536(6) . ? C24 H241 0.99 . ? C24 H242 0.99 . ? C25 C26 1.508(7) . ? C25 H251 0.99 . ? C25 H252 0.99 . ? C26 C27 1.491(9) . ? C26 H261 0.99 . ? C26 H262 0.99 . ? C27 H271 0.98 . ? C27 H272 0.98 . ? C27 H273 0.98 . ? C28 C29 1.535(6) . ? C28 H281 0.99 . ? C28 H282 0.99 . ? C29 C30 1.526(7) . ? C29 H291 0.99 . ? C29 H292 0.99 . ? C30 C31 1.533(7) . ? C30 H301 0.99 . ? C30 H302 0.99 . ? C31 C32 1.518(7) . ? C31 H311 0.99 . ? C31 H312 0.99 . ? C32 C33 1.519(7) . ? C32 H321 0.99 . ? C32 H322 0.99 . ? C33 H331 0.98 . ? C33 H332 0.98 . ? C33 H333 0.98 . ? S1 O5 1.352(10) . ? S1 O2 1.409(9) . ? S1 O7 1.426(9) . ? S1 O6 1.424(9) . ? S1 O3 1.450(9) . ? S1 O4 1.466(8) . ? S1 C34 1.790(6) . ? F1 C34 1.342(9) . ? F2 C34 1.374(10) . ? F3 C34 1.279(10) . ? F4 C34 1.356(10) . ? F5 C34 1.299(13) . ? F6 C34 1.332(12) . ? O1W H1W 0.85(6) . ? O1W H2W 0.84(6) . ? 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 C2 Se1 C8 86.34(18) . . ? C15 Se2 C21 86.7(2) . . ? C2 N1 C7 115.8(4) . . ? C2 N1 C22 123.4(4) . . ? C7 N1 C22 120.7(3) . . ? C15 N2 C20 117.3(4) . . ? C15 N2 C28 121.9(4) . . ? C20 N2 C28 120.8(4) . . ? C11 N3 C1 124.5(4) . . ? C11 N3 H31 117.7 . . ? C1 N3 H31 117.7 . . ? N3 C1 H11 109.5 . . ? N3 C1 H12 109.5 . . ? H11 C1 H12 109.5 . . ? N3 C1 H13 109.5 . . ? H11 C1 H13 109.5 . . ? H12 C1 H13 109.5 . . ? N1 C2 C9 122.3(4) . . ? N1 C2 Se1 112.0(3) . . ? C9 C2 Se1 125.7(3) . . ? C8 C3 C4 117.7(4) . . ? C8 C3 H3 121.2 . . ? C4 C3 H3 121.2 . . ? C5 C4 C3 121.5(4) . . ? C5 C4 H4 119.3 . . ? C3 C4 H4 119.3 . . ? C6 C5 C4 120.3(4) . . ? C6 C5 H5 119.9 . . ? C4 C5 H5 119.9 . . ? C5 C6 C7 119.2(4) . . ? C5 C6 H6 120.4 . . ? C7 C6 H6 120.4 . . ? N1 C7 C6 125.6(4) . . ? N1 C7 C8 114.9(4) . . ? C6 C7 C8 119.5(4) . . ? C3 C8 C7 121.8(4) . . ? C3 C8 Se1 127.3(4) . . ? C7 C8 Se1 110.9(3) . . ? C10 C9 C2 126.0(4) . . ? C10 C9 H9 117.0 . . ? C2 C9 H9 117.0 . . ? C9 C10 C11 131.4(4) . . ? C9 C10 C13 140.4(4) . . ? C11 C10 C13 88.2(3) . . ? N3 C11 C12 136.2(4) . . ? N3 C11 C10 130.0(4) . . ? C12 C11 C10 93.8(4) . . ? N3 C11 C13 177.0(4) . . ? C10 C11 C13 47.0(3) . . ? C14 C12 C11 134.3(4) . . ? C14 C12 C13 137.3(4) . . ? C11 C12 C13 88.4(3) . . ? O1 C13 C12 135.5(4) . . ? O1 C13 C10 134.9(4) . . ? C12 C13 C10 89.6(3) . . ? O1 C13 C11 179.7(4) . . ? C15 C14 C12 127.7(4) . . ? C15 C14 H14 116.2 . . ? C12 C14 H14 116.2 . . ? N2 C15 C14 123.5(4) . . ? N2 C15 Se2 110.5(3) . . ? C14 C15 Se2 126.0(3) . . ? C21 C16 C17 117.7(5) . . ? C21 C16 H16 121.2 . . ? C17 C16 H16 121.2 . . ? C18 C17 C16 121.1(5) . . ? C18 C17 H17 119.5 . . ? C16 C17 H17 119.5 . . ? C17 C18 C19 121.4(5) . . ? C17 C18 H18 119.3 . . ? C19 C18 H18 119.3 . . ? C18 C19 C20 118.3(5) . . ? C18 C19 H19 120.9 . . ? C20 C19 H19 120.9 . . ? C16 C21 C20 121.7(4) . . ? C16 C21 Se2 127.6(4) . . ? C20 C21 Se2 110.6(3) . . ? C21 C20 C19 119.7(4) . . ? C21 C20 N2 114.7(4) . . ? C19 C20 N2 125.6(4) . . ? N1 C22 C23 112.1(3) . . ? N1 C22 H221 109.2 . . ? C23 C22 H221 109.2 . . ? N1 C22 H222 109.2 . . ? C23 C22 H222 109.2 . . ? H221 C22 H222 107.9 . . ? C24 C23 C22 112.1(4) . . ? C24 C23 H231 109.2 . . ? C22 C23 H231 109.2 . . ? C24 C23 H232 109.2 . . ? C22 C23 H232 109.2 . . ? H231 C23 H232 107.9 . . ? C23 C24 C25 113.4(4) . . ? C23 C24 H241 108.9 . . ? C25 C24 H241 108.9 . . ? C23 C24 H242 108.9 . . ? C25 C24 H242 108.9 . . ? H241 C24 H242 107.7 . . ? C26 C25 C24 116.3(4) . . ? C26 C25 H251 108.2 . . ? C24 C25 H251 108.2 . . ? C26 C25 H252 108.2 . . ? C24 C25 H252 108.2 . . ? H251 C25 H252 107.4 . . ? C27 C26 C25 113.6(5) . . ? C27 C26 H261 108.9 . . ? C25 C26 H261 108.9 . . ? C27 C26 H262 108.9 . . ? C25 C26 H262 108.9 . . ? H261 C26 H262 107.7 . . ? C26 C27 H271 109.5 . . ? C26 C27 H272 109.5 . . ? H271 C27 H272 109.5 . . ? C26 C27 H273 109.5 . . ? H271 C27 H273 109.5 . . ? H272 C27 H273 109.5 . . ? N2 C28 C29 113.0(4) . . ? N2 C28 H281 109.0 . . ? C29 C28 H281 109.0 . . ? N2 C28 H282 109.0 . . ? C29 C28 H282 109.0 . . ? H281 C28 H282 107.8 . . ? C30 C29 C28 112.0(4) . . ? C30 C29 H291 109.2 . . ? C28 C29 H291 109.2 . . ? C30 C29 H292 109.2 . . ? C28 C29 H292 109.2 . . ? H291 C29 H292 107.9 . . ? C29 C30 C31 113.5(4) . . ? C29 C30 H301 108.9 . . ? C31 C30 H301 108.9 . . ? C29 C30 H302 108.9 . . ? C31 C30 H302 108.9 . . ? H301 C30 H302 107.7 . . ? C32 C31 C30 113.9(4) . . ? C32 C31 H311 108.8 . . ? C30 C31 H311 108.8 . . ? C32 C31 H312 108.8 . . ? C30 C31 H312 108.8 . . ? H311 C31 H312 107.7 . . ? C31 C32 C33 113.2(4) . . ? C31 C32 H321 108.9 . . ? C33 C32 H321 108.9 . . ? C31 C32 H322 108.9 . . ? C33 C32 H322 108.9 . . ? H321 C32 H322 107.8 . . ? C32 C33 H331 109.5 . . ? C32 C33 H332 109.5 . . ? H331 C33 H332 109.5 . . ? C32 C33 H333 109.5 . . ? H331 C33 H333 109.5 . . ? H332 C33 H333 109.5 . . ? O2 S1 O4 112.3(6) . . ? O2 S1 O6 114.3(8) . . ? O6 S1 O4 111.0(7) . . ? O5 S1 O3 120.9(8) . . ? O7 S1 O3 111.8(6) . . ? O5 S1 O7 116.2(8) . . ? O2 S1 C34 106.2(4) . . ? O3 S1 C34 99.9(4) . . ? O4 S1 C34 104.7(4) . . ? O5 S1 C34 103.5(4) . . ? O6 S1 C34 107.5(4) . . ? O7 S1 C34 99.9(4) . . ? F3 C34 F1 106.9(7) . . ? F5 C34 F1 106.2(7) . . ? F3 C34 F5 112.5(9) . . ? F4 C34 F2 103.0(7) . . ? F6 C34 F2 102.6(8) . . ? F6 C34 F4 101.3(7) . . ? F1 C34 S1 107.1(5) . . ? F2 C34 S1 117.0(5) . . ? F3 C34 S1 112.3(5) . . ? F4 C34 S1 114.7(5) . . ? F5 C34 S1 111.4(7) . . ? F6 C34 S1 116.1(6) . . ? H1W O1W H2W 107(6) . . ? 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 C7 N1 C2 C9 -177.2(4) . . . . ? C22 N1 C2 C9 4.4(6) . . . . ? C7 N1 C2 Se1 2.7(5) . . . . ? C22 N1 C2 Se1 -175.7(3) . . . . ? C8 Se1 C2 N1 -1.4(3) . . . . ? C8 Se1 C2 C9 178.5(4) . . . . ? C8 C3 C4 C5 -0.3(7) . . . . ? C3 C4 C5 C6 1.4(7) . . . . ? C4 C5 C6 C7 -1.0(7) . . . . ? C2 N1 C7 C6 177.7(4) . . . . ? C22 N1 C7 C6 -3.9(6) . . . . ? C2 N1 C7 C8 -2.8(5) . . . . ? C22 N1 C7 C8 175.6(4) . . . . ? C5 C6 C7 N1 179.1(4) . . . . ? C5 C6 C7 C8 -0.5(6) . . . . ? C4 C3 C8 C7 -1.2(6) . . . . ? C4 C3 C8 Se1 179.4(3) . . . . ? N1 C7 C8 C3 -178.0(4) . . . . ? C6 C7 C8 C3 1.6(6) . . . . ? N1 C7 C8 Se1 1.5(5) . . . . ? C6 C7 C8 Se1 -178.9(3) . . . . ? C2 Se1 C8 C3 179.4(4) . . . . ? C2 Se1 C8 C7 -0.1(3) . . . . ? N1 C2 C9 C10 -174.6(4) . . . . ? Se1 C2 C9 C10 5.6(7) . . . . ? C2 C9 C10 C11 178.2(4) . . . . ? C2 C9 C10 C13 1.5(9) . . . . ? C1 N3 C11 C12 -1.2(9) . . . . ? C1 N3 C11 C10 -179.3(5) . . . . ? C9 C10 C11 N3 1.5(8) . . . . ? C13 C10 C11 N3 179.5(5) . . . . ? C9 C10 C11 C12 -177.1(5) . . . . ? C13 C10 C11 C12 0.8(3) . . . . ? C9 C10 C11 C13 -177.9(6) . . . . ? N3 C11 C12 C14 -0.5(9) . . . . ? C10 C11 C12 C14 178.0(5) . . . . ? C13 C11 C12 C14 178.8(7) . . . . ? N3 C11 C12 C13 -179.4(5) . . . . ? C10 C11 C12 C13 -0.8(3) . . . . ? C14 C12 C13 O1 1.1(10) . . . . ? C11 C12 C13 O1 179.9(6) . . . . ? C14 C12 C13 C10 -178.0(5) . . . . ? C11 C12 C13 C10 0.8(3) . . . . ? C14 C12 C13 C11 -178.8(7) . . . . ? C9 C10 C13 O1 -2.3(10) . . . . ? C11 C10 C13 O1 -179.9(5) . . . . ? C9 C10 C13 C12 176.8(6) . . . . ? C11 C10 C13 C12 -0.8(3) . . . . ? C9 C10 C13 C11 177.6(7) . . . . ? C10 C11 C13 C12 178.9(5) . . . . ? C12 C11 C13 C10 -178.9(5) . . . . ? C11 C12 C14 C15 -178.8(5) . . . . ? C13 C12 C14 C15 -0.6(9) . . . . ? C20 N2 C15 C14 -179.3(4) . . . . ? C28 N2 C15 C14 1.7(6) . . . . ? C20 N2 C15 Se2 1.4(5) . . . . ? C28 N2 C15 Se2 -177.7(3) . . . . ? C12 C14 C15 N2 -176.9(4) . . . . ? C12 C14 C15 Se2 2.3(7) . . . . ? C21 Se2 C15 N2 0.1(3) . . . . ? C21 Se2 C15 C14 -179.2(4) . . . . ? C21 C16 C17 C18 -0.2(7) . . . . ? C16 C17 C18 C19 1.7(8) . . . . ? C17 C18 C19 C20 -0.2(7) . . . . ? C17 C16 C21 C20 -2.9(7) . . . . ? C17 C16 C21 Se2 179.2(4) . . . . ? C15 Se2 C21 C16 176.5(4) . . . . ? C15 Se2 C21 C20 -1.5(3) . . . . ? C16 C21 C20 C19 4.4(7) . . . . ? Se2 C21 C20 C19 -177.3(3) . . . . ? C16 C21 C20 N2 -175.5(4) . . . . ? Se2 C21 C20 N2 2.7(5) . . . . ? C18 C19 C20 C21 -2.8(7) . . . . ? C18 C19 C20 N2 177.2(4) . . . . ? C15 N2 C20 C21 -2.8(6) . . . . ? C28 N2 C20 C21 176.3(4) . . . . ? C15 N2 C20 C19 177.2(4) . . . . ? C28 N2 C20 C19 -3.7(7) . . . . ? C2 N1 C22 C23 -92.5(5) . . . . ? C7 N1 C22 C23 89.2(5) . . . . ? N1 C22 C23 C24 -173.1(4) . . . . ? C22 C23 C24 C25 175.1(4) . . . . ? C23 C24 C25 C26 67.3(6) . . . . ? C24 C25 C26 C27 64.8(6) . . . . ? C15 N2 C28 C29 -91.4(5) . . . . ? C20 N2 C28 C29 89.5(5) . . . . ? N2 C28 C29 C30 168.7(4) . . . . ? C28 C29 C30 C31 -82.8(5) . . . . ? C29 C30 C31 C32 -179.8(4) . . . . ? C30 C31 C32 C33 -175.1(4) . . . . ? _geom_special_details ; Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) 6.1941 (0.0199) x - 11.2534 (0.0121) y - 2.6635 (0.0231) z = 1.3797 (0.0156) * 0.0028 (0.0031) C3 * 0.0063 (0.0032) C4 * -0.0087 (0.0032) C5 * 0.0022 (0.0031) C6 * 0.0068 (0.0030) C7 * -0.0094 (0.0030) C8 Rms deviation of fitted atoms = 0.0066 6.9411 (0.0307) x - 11.6524 (0.0181) y - 1.9245 (0.0391) z = 1.6874 (0.0077) Angle to previous plane (with approximate esd) = 5.26 ( 0.38 ) * 0.0051 (0.0021) C10 * -0.0053 (0.0022) C11 * 0.0052 (0.0022) C12 * -0.0050 (0.0021) C13 Rms deviation of fitted atoms = 0.0052 7.0373 (0.0202) x - 11.5328 (0.0119) y - 2.1775 (0.0247) z = 1.7875 (0.0082) Angle to previous plane (with approximate esd) = 1.19 ( 0.38 ) * -0.0047 (0.0034) C16 * -0.0112 (0.0035) C17 * 0.0110 (0.0034) C18 * 0.0048 (0.0033) C19 * 0.0206 (0.0031) C21 * -0.0205 (0.0031) C20 Rms deviation of fitted atoms = 0.0138 6.1941 (0.0199) x - 11.2534 (0.0121) y - 2.6635 (0.0231) z = 1.3797 (0.0156) Angle to previous plane (with approximate esd) = 5.03 ( 0.29 ) * 0.0028 (0.0031) C3 * 0.0063 (0.0032) C4 * -0.0087 (0.0032) C5 * 0.0022 (0.0031) C6 * 0.0068 (0.0030) C7 * -0.0094 (0.0030) C8 Rms deviation of fitted atoms = 0.0066 ; loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N3 H31 O1W 0.88 2.00 2.880(5) 173.0 . O1W H1W O4 0.85(6) 2.09(6) 2.847(10) 149(6) 2_656 O1W H1W O3 0.85(6) 2.06(6) 2.862(11) 159(6) 2_656 O1W H2W O2 0.84(6) 1.93(6) 2.675(10) 146(6) . O1W H2W O3 0.84(6) 2.01(7) 2.817(11) 160(6) . O1W H2W S1 0.84(6) 3.12(6) 3.932(4) 164(5) . _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.616 _refine_diff_density_min -0.464 _refine_diff_density_rms 0.103 #========================================================== # END of CIF #========================================================== data_7 _database_code_depnum_ccdc_archive 'CCDC 751395' #TrackingRef '- RSC Article.cif.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2-[2-Diethylamino-3-hexyl-2-[3-(3-hexyl-3H-benzoselenazol-2-ylidenemethyl)-4- oxocyclobut-2-enylidenemethyl]-3-hexylbenzoselenazol-3-ium trifluoromethanesulfonate ; _chemical_name_common ; 2-(2-Diethylamino-3-hexyl-2-(3-(3-hexyl-3H-benzoselenazol-2- ylidenemethyl)-4-oxocyclobut-2-enylidenemethyl)-3-hexylbenzoselenazol-3- ium trifluoromethanesulfonate ; _chemical_melting_point ? _chemical_formula_moiety 'C36 H46 N3 O Se2, C F3 O3 S' _chemical_formula_sum 'C37 H46 F3 N3 O4 S Se2' _chemical_formula_weight 843.75 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' S S 0.1246 0.1234 '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' Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 23.4215(9) _cell_length_b 13.4127(3) _cell_length_c 25.2899(9) _cell_angle_alpha 90.00 _cell_angle_beta 112.4820(10) _cell_angle_gamma 90.00 _cell_volume 7340.9(4) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 22486 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Plate _exptl_crystal_colour Blue _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.527 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3456 _exptl_absorpt_coefficient_mu 2.130 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.675 _exptl_absorpt_correction_T_max 0.939 _exptl_absorpt_process_details '(SADABS; Sheldrick, 2003)' _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius Roper CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 35737 _diffrn_reflns_av_R_equivalents 0.1047 _diffrn_reflns_av_sigmaI/netI 0.0888 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 3.02 _diffrn_reflns_theta_max 25.03 _reflns_number_total 6465 _reflns_number_gt 4298 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'COLLECT (Hooft, 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) and COLLECT' _computing_data_reduction 'DENZO and COLLECT' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material SHELXL97 _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0399P)^2^+23.5518P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6465 _refine_ls_number_parameters 455 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0955 _refine_ls_R_factor_gt 0.0501 _refine_ls_wR_factor_ref 0.1127 _refine_ls_wR_factor_gt 0.0960 _refine_ls_goodness_of_fit_ref 0.984 _refine_ls_restrained_S_all 0.984 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 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 Se1 Se -0.01433(2) 0.07964(3) -0.07919(2) 0.02205(15) Uani 1 1 d . . . Se2 Se 0.23817(2) 0.08037(3) -0.00310(2) 0.01982(14) Uani 1 1 d . . . O1 O 0.11340(16) 0.0933(2) -0.01414(15) 0.0316(9) Uani 1 1 d . . . N1 N -0.09684(18) 0.1239(3) -0.03220(16) 0.0176(9) Uani 1 1 d . . . N2 N 0.32670(18) 0.1889(3) 0.07708(17) 0.0205(9) Uani 1 1 d . . . N3 N 0.12108(18) 0.3037(3) 0.13176(17) 0.0232(10) Uani 1 1 d . . . C2 C -0.0355(2) 0.1344(3) -0.0200(2) 0.0205(11) Uani 1 1 d . . . C3 C -0.1281(2) 0.0102(3) -0.1713(2) 0.0265(12) Uani 1 1 d . . . H3 H -0.1049 -0.0087 -0.1933 0.033 Uiso 1 1 calc R . . C4 C -0.1914(2) -0.0046(3) -0.1921(2) 0.0260(12) Uani 1 1 d . . . H4 H -0.2119 -0.0345 -0.2286 0.032 Uiso 1 1 calc R . . C5 C -0.2252(3) 0.0245(4) -0.1596(2) 0.0288(13) Uani 1 1 d . . . H5 H -0.2686 0.0142 -0.1743 0.036 Uiso 1 1 calc R . . C6 C -0.1967(2) 0.0679(3) -0.1066(2) 0.0232(11) Uani 1 1 d . . . H6 H -0.2201 0.0881 -0.0849 0.029 Uiso 1 1 calc R . . C7 C -0.1333(2) 0.0816(3) -0.08553(19) 0.0189(11) Uani 1 1 d . . . C8 C -0.0992(2) 0.0530(3) -0.1178(2) 0.0195(11) Uani 1 1 d . . . C9 C 0.0054(2) 0.1828(3) 0.0289(2) 0.0215(11) Uani 1 1 d . . . H9 H -0.0121 0.2137 0.0530 0.027 Uiso 1 1 calc R . . C10 C 0.0689(2) 0.1899(3) 0.0455(2) 0.0200(11) Uani 1 1 d . . . C11 C 0.1190(2) 0.2417(3) 0.0901(2) 0.0233(12) Uani 1 1 d . . . C12 C 0.1649(2) 0.2038(3) 0.0697(2) 0.0172(11) Uani 1 1 d . . . C13 C 0.1154(2) 0.1498(3) 0.0245(2) 0.0212(11) Uani 1 1 d . . . C14 C 0.2281(2) 0.2145(3) 0.0856(2) 0.0203(11) Uani 1 1 d . . . H14 H 0.2488 0.2560 0.1177 0.025 Uiso 1 1 calc R . . C15 C 0.2646(2) 0.1707(3) 0.0593(2) 0.0176(11) Uani 1 1 d . . . C16 C 0.3452(2) 0.0269(3) -0.0309(2) 0.0260(12) Uani 1 1 d . . . H16 H 0.3195 -0.0140 -0.0615 0.033 Uiso 1 1 calc R . . C17 C 0.4079(2) 0.0363(3) -0.0195(2) 0.0263(13) Uani 1 1 d . . . H17 H 0.4251 0.0023 -0.0429 0.033 Uiso 1 1 calc R . . C18 C 0.4456(2) 0.0943(3) 0.0255(2) 0.0265(12) Uani 1 1 d . . . H18 H 0.4884 0.0993 0.0327 0.033 Uiso 1 1 calc R . . C19 C 0.4217(2) 0.1458(3) 0.0604(2) 0.0270(12) Uani 1 1 d . . . H19 H 0.4478 0.1846 0.0918 0.034 Uiso 1 1 calc R . . C20 C 0.3582(2) 0.1389(3) 0.0479(2) 0.0201(11) Uani 1 1 d . . . C21 C 0.3209(2) 0.0784(3) 0.0032(2) 0.0199(11) Uani 1 1 d . . . C22 C -0.1259(2) 0.1588(3) 0.0073(2) 0.0210(11) Uani 1 1 d . . . H221 H -0.0950 0.1573 0.0471 0.026 Uiso 1 1 calc R . . H222 H -0.1601 0.1132 0.0049 0.026 Uiso 1 1 calc R . . C23 C -0.1511(2) 0.2649(3) -0.0075(2) 0.0184(11) Uani 1 1 d . . . H231 H -0.1868 0.2641 -0.0447 0.023 Uiso 1 1 calc R . . H232 H -0.1188 0.3079 -0.0118 0.023 Uiso 1 1 calc R . . C24 C -0.1715(2) 0.3095(3) 0.0383(2) 0.0219(11) Uani 1 1 d . . . H241 H -0.2008 0.3647 0.0213 0.027 Uiso 1 1 calc R . . H242 H -0.1933 0.2577 0.0513 0.027 Uiso 1 1 calc R . . C25 C -0.1168(2) 0.3490(3) 0.0902(2) 0.0253(12) Uani 1 1 d . . . H251 H -0.0870 0.2940 0.1066 0.032 Uiso 1 1 calc R . . H252 H -0.0954 0.4015 0.0772 0.032 Uiso 1 1 calc R . . C26 C -0.1360(2) 0.3917(4) 0.1367(2) 0.0292(13) Uani 1 1 d . . . H261 H -0.1612 0.3416 0.1468 0.037 Uiso 1 1 calc R . . H262 H -0.1623 0.4511 0.1214 0.037 Uiso 1 1 calc R . . C27 C -0.0807(3) 0.4213(4) 0.1911(2) 0.0424(15) Uani 1 1 d . . . H271 H -0.0577 0.3613 0.2094 0.053 Uiso 1 1 calc R . . H272 H -0.0956 0.4553 0.2176 0.053 Uiso 1 1 calc R . . H273 H -0.0535 0.4662 0.1809 0.053 Uiso 1 1 calc R . . C28 C 0.3598(2) 0.2559(3) 0.1258(2) 0.0238(12) Uani 1 1 d . . . H281 H 0.3326 0.3122 0.1260 0.030 Uiso 1 1 calc R . . H282 H 0.3969 0.2835 0.1213 0.030 Uiso 1 1 calc R . . C29 C 0.3793(2) 0.1999(4) 0.1825(2) 0.0292(13) Uani 1 1 d . . . H291 H 0.3426 0.1683 0.1857 0.036 Uiso 1 1 calc R . . H292 H 0.4087 0.1463 0.1832 0.036 Uiso 1 1 calc R . . C30 C 0.4096(3) 0.2688(4) 0.2334(2) 0.0355(14) Uani 1 1 d . . . H301 H 0.4456 0.3018 0.2296 0.044 Uiso 1 1 calc R . . H302 H 0.3798 0.3213 0.2332 0.044 Uiso 1 1 calc R . . C31 C 0.4307(3) 0.2138(4) 0.2900(2) 0.0458(16) Uani 1 1 d . . . H311 H 0.4595 0.2567 0.3204 0.057 Uiso 1 1 calc R . . H312 H 0.4533 0.1528 0.2875 0.057 Uiso 1 1 calc R . . C32 C 0.3751(4) 0.1849(6) 0.3059(3) 0.076(2) Uani 1 1 d . . . H321 H 0.3501 0.2455 0.3036 0.095 Uiso 1 1 calc R . . H322 H 0.3488 0.1372 0.2770 0.095 Uiso 1 1 calc R . . C33 C 0.3907(4) 0.1416(6) 0.3614(3) 0.081(3) Uani 1 1 d . . . H331 H 0.4148 0.0807 0.3642 0.101 Uiso 1 1 calc R . . H332 H 0.3527 0.1252 0.3672 0.101 Uiso 1 1 calc R . . H333 H 0.4152 0.1891 0.3907 0.101 Uiso 1 1 calc R . . C34 C 0.0675(2) 0.3191(4) 0.1475(2) 0.0313(13) Uani 1 1 d . . . H341 H 0.0302 0.3299 0.1124 0.039 Uiso 1 1 calc R . . H342 H 0.0742 0.3799 0.1714 0.039 Uiso 1 1 calc R . . C35 C 0.0564(3) 0.2313(4) 0.1803(3) 0.0402(15) Uani 1 1 d . . . H351 H 0.0475 0.1716 0.1561 0.050 Uiso 1 1 calc R . . H352 H 0.0212 0.2458 0.1909 0.050 Uiso 1 1 calc R . . H353 H 0.0933 0.2198 0.2149 0.050 Uiso 1 1 calc R . . C36 C 0.1797(2) 0.3534(3) 0.1674(2) 0.0283(13) Uani 1 1 d . . . H361 H 0.1700 0.4174 0.1816 0.035 Uiso 1 1 calc R . . H362 H 0.2032 0.3689 0.1431 0.035 Uiso 1 1 calc R . . C37 C 0.2200(3) 0.2920(4) 0.2177(2) 0.0401(15) Uani 1 1 d . . . H371 H 0.1988 0.2821 0.2441 0.050 Uiso 1 1 calc R . . H372 H 0.2591 0.3268 0.2376 0.050 Uiso 1 1 calc R . . H373 H 0.2281 0.2271 0.2042 0.050 Uiso 1 1 calc R . . S1 S 0.18566(6) 0.05975(9) 0.34813(6) 0.0265(3) Uani 1 1 d . . . O2 O 0.20997(17) 0.0869(3) 0.40800(15) 0.0369(9) Uani 1 1 d . . . O3 O 0.20111(16) -0.0401(2) 0.33677(16) 0.0363(9) Uani 1 1 d . . . O4 O 0.19088(19) 0.1346(3) 0.30942(16) 0.0430(10) Uani 1 1 d . . . F1 F 0.07946(16) 0.1404(2) 0.33696(15) 0.0534(10) Uani 1 1 d . . . F2 F 0.08829(15) -0.0124(2) 0.36275(14) 0.0495(9) Uani 1 1 d . . . F3 F 0.07174(14) 0.0251(2) 0.27559(14) 0.0442(8) Uani 1 1 d . . . C1 C 0.1024(3) 0.0527(4) 0.3297(2) 0.0325(13) Uani 1 1 d . . . 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 0.0219(3) 0.0241(3) 0.0237(3) -0.0007(2) 0.0127(2) 0.0026(2) Se2 0.0175(3) 0.0209(3) 0.0229(3) -0.0006(2) 0.0098(2) 0.0006(2) O1 0.025(2) 0.038(2) 0.034(2) -0.0115(18) 0.0147(18) 0.0006(17) N1 0.016(2) 0.019(2) 0.020(2) -0.0017(17) 0.009(2) -0.0035(17) N2 0.019(2) 0.023(2) 0.021(2) 0.0027(18) 0.009(2) 0.0047(19) N3 0.020(2) 0.028(2) 0.024(3) -0.0062(19) 0.012(2) 0.0005(19) C2 0.027(3) 0.016(2) 0.023(3) 0.003(2) 0.015(3) 0.004(2) C3 0.036(3) 0.027(3) 0.021(3) 0.001(2) 0.017(3) 0.000(3) C4 0.030(3) 0.028(3) 0.018(3) -0.004(2) 0.007(3) -0.002(2) C5 0.029(3) 0.031(3) 0.022(3) -0.004(2) 0.005(3) -0.005(2) C6 0.018(3) 0.034(3) 0.018(3) 0.001(2) 0.007(2) 0.000(2) C7 0.025(3) 0.013(2) 0.015(3) 0.000(2) 0.004(2) 0.001(2) C8 0.024(3) 0.020(2) 0.018(3) 0.000(2) 0.011(2) 0.000(2) C9 0.024(3) 0.020(3) 0.022(3) -0.001(2) 0.011(3) 0.000(2) C10 0.020(3) 0.017(2) 0.026(3) 0.002(2) 0.012(2) 0.002(2) C11 0.024(3) 0.020(3) 0.029(3) 0.005(2) 0.014(3) -0.003(2) C12 0.017(3) 0.020(2) 0.018(3) 0.004(2) 0.009(2) -0.002(2) C13 0.018(3) 0.022(3) 0.026(3) 0.005(2) 0.010(2) 0.005(2) C14 0.020(3) 0.017(2) 0.024(3) 0.003(2) 0.008(2) 0.002(2) C15 0.015(3) 0.018(2) 0.019(3) 0.001(2) 0.007(2) 0.001(2) C16 0.030(3) 0.021(3) 0.030(3) 0.002(2) 0.015(3) 0.006(2) C17 0.028(3) 0.028(3) 0.032(3) 0.007(2) 0.022(3) 0.012(2) C18 0.017(3) 0.027(3) 0.035(3) 0.008(2) 0.009(3) 0.007(2) C19 0.019(3) 0.024(3) 0.036(3) 0.001(2) 0.008(3) 0.002(2) C20 0.017(3) 0.022(3) 0.024(3) 0.003(2) 0.010(2) -0.001(2) C21 0.017(3) 0.018(2) 0.025(3) 0.007(2) 0.008(2) 0.003(2) C22 0.020(3) 0.026(3) 0.022(3) -0.003(2) 0.014(2) -0.004(2) C23 0.018(3) 0.021(3) 0.016(3) 0.003(2) 0.006(2) 0.003(2) C24 0.019(3) 0.022(3) 0.026(3) 0.001(2) 0.009(3) 0.004(2) C25 0.025(3) 0.022(3) 0.030(3) 0.004(2) 0.012(3) 0.005(2) C26 0.034(3) 0.028(3) 0.026(3) -0.001(2) 0.012(3) 0.008(2) C27 0.048(4) 0.044(3) 0.030(3) -0.001(3) 0.009(3) 0.018(3) C28 0.013(3) 0.025(3) 0.031(3) -0.006(2) 0.005(2) -0.003(2) C29 0.032(3) 0.027(3) 0.023(3) -0.001(2) 0.005(3) 0.003(2) C30 0.030(3) 0.036(3) 0.034(4) -0.008(3) 0.006(3) 0.002(3) C31 0.050(4) 0.054(4) 0.026(4) -0.005(3) 0.006(3) -0.015(3) C32 0.074(6) 0.092(6) 0.045(5) 0.004(4) 0.004(4) -0.033(5) C33 0.105(7) 0.089(6) 0.051(5) -0.010(4) 0.033(5) -0.029(5) C34 0.029(3) 0.034(3) 0.035(3) -0.002(3) 0.017(3) 0.002(3) C35 0.028(3) 0.056(4) 0.041(4) 0.002(3) 0.018(3) -0.004(3) C36 0.030(3) 0.026(3) 0.029(3) -0.010(2) 0.011(3) -0.003(2) C37 0.037(4) 0.040(3) 0.043(4) -0.001(3) 0.014(3) -0.007(3) S1 0.0303(8) 0.0260(7) 0.0252(8) 0.0028(6) 0.0129(7) 0.0025(6) O2 0.041(2) 0.040(2) 0.028(2) -0.0030(17) 0.0108(19) -0.0002(19) O3 0.032(2) 0.0296(19) 0.052(3) -0.0007(18) 0.022(2) 0.0082(17) O4 0.053(3) 0.038(2) 0.040(3) 0.0136(19) 0.020(2) -0.002(2) F1 0.047(2) 0.047(2) 0.064(3) -0.0089(18) 0.020(2) 0.0249(17) F2 0.038(2) 0.069(2) 0.053(2) 0.0157(18) 0.0299(19) 0.0036(17) F3 0.034(2) 0.064(2) 0.033(2) -0.0091(16) 0.0110(17) 0.0020(17) C1 0.035(3) 0.033(3) 0.032(4) 0.003(3) 0.016(3) 0.009(3) 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 C8 1.884(5) . ? Se1 C2 1.897(4) . ? Se2 C21 1.881(5) . ? Se2 C15 1.896(5) . ? O1 C13 1.223(5) . ? N1 C2 1.355(6) . ? N1 C7 1.411(6) . ? N1 C22 1.483(5) . ? N2 C15 1.370(6) . ? N2 C20 1.398(6) . ? N2 C28 1.483(6) . ? N3 C11 1.330(6) . ? N3 C34 1.470(6) . ? N3 C36 1.482(6) . ? C2 C9 1.400(7) . ? C3 C4 1.385(7) . ? C3 C8 1.384(7) . ? C3 H3 0.95 . ? C4 C5 1.398(7) . ? C4 H4 0.95 . ? C5 C6 1.377(7) . ? C5 H5 0.95 . ? C6 C7 1.386(7) . ? C6 H6 0.95 . ? C7 C8 1.395(6) . ? C9 C10 1.386(7) . ? C9 H9 0.95 . ? C10 C11 1.455(7) . ? C10 C13 1.483(6) . ? C11 C12 1.450(6) . ? C12 C14 1.385(6) . ? C12 C13 1.471(7) . ? C14 C15 1.397(6) . ? C14 H14 0.95 . ? C16 C17 1.390(7) . ? C16 C21 1.387(6) . ? C16 H16 0.95 . ? C17 C18 1.383(7) . ? C17 H17 0.95 . ? C18 C19 1.396(7) . ? C18 H18 0.95 . ? C19 C20 1.400(7) . ? C19 H19 0.95 . ? C20 C21 1.394(7) . ? C22 C23 1.531(6) . ? C22 H221 0.99 . ? C22 H222 0.99 . ? C23 C24 1.533(6) . ? C23 H231 0.99 . ? C23 H232 0.99 . ? C24 C25 1.535(7) . ? C24 H241 0.99 . ? C24 H242 0.99 . ? C25 C26 1.523(6) . ? C25 H251 0.99 . ? C25 H252 0.99 . ? C26 C27 1.539(7) . ? C26 H261 0.99 . ? C26 H262 0.99 . ? C27 H271 0.98 . ? C27 H272 0.98 . ? C27 H273 0.98 . ? C28 C29 1.526(7) . ? C28 H281 0.99 . ? C28 H282 0.99 . ? C29 C30 1.521(7) . ? C29 H291 0.99 . ? C29 H292 0.99 . ? C30 C31 1.514(7) . ? C30 H301 0.99 . ? C30 H302 0.99 . ? C31 C32 1.553(9) . ? C31 H311 0.99 . ? C31 H312 0.99 . ? C32 C33 1.430(9) . ? C32 H321 0.99 . ? C32 H322 0.99 . ? C33 H331 0.98 . ? C33 H332 0.98 . ? C33 H333 0.98 . ? C34 C35 1.518(7) . ? C34 H341 0.99 . ? C34 H342 0.99 . ? C35 H351 0.98 . ? C35 H352 0.98 . ? C35 H353 0.98 . ? C36 C37 1.507(7) . ? C36 H361 0.99 . ? C36 H362 0.99 . ? C37 H371 0.98 . ? C37 H372 0.98 . ? C37 H373 0.98 . ? S1 O4 1.439(4) . ? S1 O3 1.444(3) . ? S1 O2 1.446(4) . ? S1 C1 1.827(6) . ? F1 C1 1.334(5) . ? F2 C1 1.334(6) . ? F3 C1 1.332(6) . ? 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 C8 Se1 C2 86.5(2) . . ? C21 Se2 C15 86.6(2) . . ? C2 N1 C7 117.5(4) . . ? C2 N1 C22 122.2(4) . . ? C7 N1 C22 120.3(4) . . ? C15 N2 C20 116.7(4) . . ? C15 N2 C28 122.2(4) . . ? C20 N2 C28 121.1(4) . . ? C11 N3 C34 121.8(4) . . ? C11 N3 C36 120.5(4) . . ? C34 N3 C36 117.5(4) . . ? N1 C2 C9 123.9(4) . . ? N1 C2 Se1 110.7(3) . . ? C9 C2 Se1 125.3(4) . . ? C4 C3 C8 118.9(5) . . ? C4 C3 H3 120.5 . . ? C8 C3 H3 120.5 . . ? C3 C4 C5 120.0(5) . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? C6 C5 C4 121.3(5) . . ? C6 C5 H5 119.3 . . ? C4 C5 H5 119.3 . . ? C5 C6 C7 118.5(5) . . ? C5 C6 H6 120.7 . . ? C7 C6 H6 120.7 . . ? C6 C7 C8 120.6(4) . . ? C6 C7 N1 126.0(4) . . ? C8 C7 N1 113.4(4) . . ? C3 C8 C7 120.7(5) . . ? C3 C8 Se1 127.6(4) . . ? C7 C8 Se1 111.8(3) . . ? C10 C9 C2 126.4(4) . . ? C10 C9 H9 116.8 . . ? C2 C9 H9 116.8 . . ? C9 C10 C11 136.2(4) . . ? C9 C10 C13 135.7(5) . . ? C11 C10 C13 88.1(4) . . ? N3 C11 C12 134.0(5) . . ? N3 C11 C10 133.4(4) . . ? C12 C11 C10 92.6(4) . . ? C14 C12 C11 135.7(4) . . ? C14 C12 C13 135.6(4) . . ? C11 C12 C13 88.7(4) . . ? O1 C13 C12 134.8(4) . . ? O1 C13 C10 134.6(5) . . ? C12 C13 C10 90.6(4) . . ? C12 C14 C15 126.7(5) . . ? C12 C14 H14 116.6 . . ? C15 C14 H14 116.6 . . ? N2 C15 C14 122.3(4) . . ? N2 C15 Se2 110.8(3) . . ? C14 C15 Se2 126.9(4) . . ? C17 C16 C21 118.5(5) . . ? C17 C16 H16 120.8 . . ? C21 C16 H16 120.8 . . ? C18 C17 C16 121.0(4) . . ? C18 C17 H17 119.5 . . ? C16 C17 H17 119.5 . . ? C17 C18 C19 120.8(5) . . ? C17 C18 H18 119.6 . . ? C19 C18 H18 119.6 . . ? C18 C19 C20 118.3(5) . . ? C18 C19 H19 120.9 . . ? C20 C19 H19 120.9 . . ? C21 C20 N2 114.4(4) . . ? C21 C20 C19 120.3(4) . . ? N2 C20 C19 125.3(5) . . ? C16 C21 C20 121.0(4) . . ? C16 C21 Se2 127.5(4) . . ? C20 C21 Se2 111.5(3) . . ? N1 C22 C23 111.2(4) . . ? N1 C22 H221 109.4 . . ? C23 C22 H221 109.4 . . ? N1 C22 H222 109.4 . . ? C23 C22 H222 109.4 . . ? H221 C22 H222 108.0 . . ? C22 C23 C24 112.3(4) . . ? C22 C23 H231 109.2 . . ? C24 C23 H231 109.2 . . ? C22 C23 H232 109.2 . . ? C24 C23 H232 109.2 . . ? H231 C23 H232 107.9 . . ? C25 C24 C23 112.4(4) . . ? C25 C24 H241 109.1 . . ? C23 C24 H241 109.1 . . ? C25 C24 H242 109.1 . . ? C23 C24 H242 109.1 . . ? H241 C24 H242 107.8 . . ? C26 C25 C24 113.1(4) . . ? C26 C25 H251 109.0 . . ? C24 C25 H251 109.0 . . ? C26 C25 H252 109.0 . . ? C24 C25 H252 109.0 . . ? H251 C25 H252 107.8 . . ? C25 C26 C27 113.0(4) . . ? C25 C26 H261 109.0 . . ? C27 C26 H261 109.0 . . ? C25 C26 H262 109.0 . . ? C27 C26 H262 109.0 . . ? H261 C26 H262 107.8 . . ? C26 C27 H271 109.5 . . ? C26 C27 H272 109.5 . . ? H272 C27 H271 109.5 . . ? C26 C27 H273 109.5 . . ? H271 C27 H273 109.5 . . ? H271 C27 H273 109.5 . . ? N2 C28 C29 110.9(4) . . ? N2 C28 H281 109.5 . . ? C29 C28 H281 109.5 . . ? N2 C28 H282 109.5 . . ? C29 C28 H282 109.5 . . ? H281 C28 H282 108.1 . . ? C30 C29 C28 111.8(4) . . ? C30 C29 H291 109.3 . . ? C28 C29 H291 109.3 . . ? C30 C29 H292 109.3 . . ? C28 C29 H292 109.3 . . ? H291 C29 H292 107.9 . . ? C31 C30 C29 112.4(4) . . ? C31 C30 H301 109.1 . . ? C29 C30 H301 109.1 . . ? C31 C30 H302 109.1 . . ? C29 C30 H302 109.1 . . ? H301 C30 H302 107.8 . . ? C30 C31 C32 111.3(5) . . ? C30 C31 H311 109.4 . . ? C32 C31 H311 109.4 . . ? C30 C31 H312 109.4 . . ? C32 C31 H312 109.4 . . ? H311 C31 H312 108.0 . . ? C33 C32 C31 115.6(6) . . ? C33 C32 H321 108.4 . . ? C31 C32 H321 108.4 . . ? C33 C32 H322 108.4 . . ? C31 C32 H322 108.4 . . ? H321 C32 H322 107.4 . . ? C32 C33 H331 109.5 . . ? C32 C33 H332 109.5 . . ? H331 C33 H332 109.5 . . ? C32 C33 H333 109.5 . . ? H331 C33 H333 109.5 . . ? H332 C33 H333 109.5 . . ? N3 C34 C35 112.5(4) . . ? N3 C34 H341 109.1 . . ? C35 C34 H341 109.1 . . ? N3 C34 H342 109.1 . . ? C35 C34 H342 109.1 . . ? H341 C34 H342 107.8 . . ? C34 C35 H351 109.5 . . ? C34 C35 H352 109.5 . . ? H351 C35 H352 109.5 . . ? C34 C35 H353 109.5 . . ? H351 C35 H353 109.5 . . ? H352 C35 H353 109.5 . . ? N3 C36 C37 113.7(4) . . ? N3 C36 H361 108.8 . . ? C37 C36 H361 108.8 . . ? N3 C36 H362 108.8 . . ? C37 C36 H362 108.8 . . ? H361 C36 H362 107.7 . . ? C36 C37 H371 109.5 . . ? C36 C37 H372 109.5 . . ? H371 C37 H372 109.5 . . ? C36 C37 H373 109.5 . . ? H371 C37 H373 109.5 . . ? H372 C37 H373 109.5 . . ? O4 S1 O3 114.7(2) . . ? O4 S1 O2 115.8(2) . . ? O3 S1 O2 114.4(2) . . ? O4 S1 C1 102.9(2) . . ? O3 S1 C1 103.0(2) . . ? O2 S1 C1 103.6(2) . . ? F2 C1 F1 106.5(4) . . ? F2 C1 F3 107.3(4) . . ? F1 C1 F3 107.4(4) . . ? F2 C1 S1 111.7(4) . . ? F1 C1 S1 111.4(4) . . ? F3 C1 S1 112.3(4) . . ? 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 C7 N1 C2 C9 174.3(4) . . . . ? C22 N1 C2 C9 -3.3(7) . . . . ? C7 N1 C2 Se1 -3.4(5) . . . . ? C22 N1 C2 Se1 179.0(3) . . . . ? C8 Se1 C2 N1 2.8(3) . . . . ? C8 Se1 C2 C9 -174.8(4) . . . . ? C8 C3 C4 C5 0.7(7) . . . . ? C3 C4 C5 C6 -0.1(7) . . . . ? C4 C5 C6 C7 -0.6(7) . . . . ? C5 C6 C7 C8 0.8(7) . . . . ? C5 C6 C7 N1 -179.5(4) . . . . ? C2 N1 C7 C6 -177.6(4) . . . . ? C22 N1 C7 C6 0.0(7) . . . . ? C2 N1 C7 C8 2.0(6) . . . . ? C22 N1 C7 C8 179.7(4) . . . . ? C4 C3 C8 C7 -0.5(7) . . . . ? C4 C3 C8 Se1 179.1(4) . . . . ? C6 C7 C8 C3 -0.2(7) . . . . ? N1 C7 C8 C3 -179.9(4) . . . . ? C6 C7 C8 Se1 -179.9(3) . . . . ? N1 C7 C8 Se1 0.4(5) . . . . ? C2 Se1 C8 C3 178.6(4) . . . . ? C2 Se1 C8 C7 -1.8(3) . . . . ? N1 C2 C9 C10 175.4(4) . . . . ? Se1 C2 C9 C10 -7.3(7) . . . . ? C2 C9 C10 C11 173.5(5) . . . . ? C2 C9 C10 C13 -4.5(9) . . . . ? C34 N3 C11 C12 -172.0(5) . . . . ? C36 N3 C11 C12 2.7(8) . . . . ? C34 N3 C11 C10 11.9(8) . . . . ? C36 N3 C11 C10 -173.5(5) . . . . ? C9 C10 C11 N3 -0.9(10) . . . . ? C13 C10 C11 N3 177.7(5) . . . . ? C9 C10 C11 C12 -178.1(5) . . . . ? C13 C10 C11 C12 0.5(4) . . . . ? N3 C11 C12 C14 1.8(9) . . . . ? C10 C11 C12 C14 179.1(5) . . . . ? N3 C11 C12 C13 -177.7(5) . . . . ? C10 C11 C12 C13 -0.5(4) . . . . ? C14 C12 C13 O1 2.2(10) . . . . ? C11 C12 C13 O1 -178.2(6) . . . . ? C14 C12 C13 C10 -179.1(5) . . . . ? C11 C12 C13 C10 0.5(3) . . . . ? C9 C10 C13 O1 -3.1(10) . . . . ? C11 C10 C13 O1 178.2(6) . . . . ? C9 C10 C13 C12 178.1(5) . . . . ? C11 C10 C13 C12 -0.5(3) . . . . ? C11 C12 C14 C15 -179.7(5) . . . . ? C13 C12 C14 C15 -0.3(9) . . . . ? C20 N2 C15 C14 178.8(4) . . . . ? C28 N2 C15 C14 0.5(7) . . . . ? C20 N2 C15 Se2 -0.8(5) . . . . ? C28 N2 C15 Se2 -179.2(3) . . . . ? C12 C14 C15 N2 177.5(4) . . . . ? C12 C14 C15 Se2 -2.9(7) . . . . ? C21 Se2 C15 N2 0.0(3) . . . . ? C21 Se2 C15 C14 -179.6(4) . . . . ? C21 C16 C17 C18 1.0(7) . . . . ? C16 C17 C18 C19 -0.5(7) . . . . ? C17 C18 C19 C20 -1.3(7) . . . . ? C15 N2 C20 C21 1.5(6) . . . . ? C28 N2 C20 C21 179.8(4) . . . . ? C15 N2 C20 C19 -178.6(4) . . . . ? C28 N2 C20 C19 -0.2(7) . . . . ? C18 C19 C20 C21 2.7(7) . . . . ? C18 C19 C20 N2 -177.2(4) . . . . ? C17 C16 C21 C20 0.4(7) . . . . ? C17 C16 C21 Se2 179.3(3) . . . . ? N2 C20 C21 C16 177.7(4) . . . . ? C19 C20 C21 C16 -2.3(7) . . . . ? N2 C20 C21 Se2 -1.4(5) . . . . ? C19 C20 C21 Se2 178.7(4) . . . . ? C15 Se2 C21 C16 -178.2(4) . . . . ? C15 Se2 C21 C20 0.8(3) . . . . ? C2 N1 C22 C23 93.1(5) . . . . ? C7 N1 C22 C23 -84.5(5) . . . . ? N1 C22 C23 C24 -170.3(4) . . . . ? C22 C23 C24 C25 79.9(5) . . . . ? C23 C24 C25 C26 -178.9(4) . . . . ? C24 C25 C26 C27 174.1(4) . . . . ? C15 N2 C28 C29 84.9(5) . . . . ? C20 N2 C28 C29 -93.4(5) . . . . ? N2 C28 C29 C30 -176.2(4) . . . . ? C28 C29 C30 C31 -178.5(5) . . . . ? C29 C30 C31 C32 -74.1(6) . . . . ? C30 C31 C32 C33 -174.0(6) . . . . ? C11 N3 C34 C35 74.0(6) . . . . ? C36 N3 C34 C35 -100.8(5) . . . . ? C11 N3 C36 C37 -86.0(6) . . . . ? C34 N3 C36 C37 88.9(5) . . . . ? O4 S1 C1 F2 -178.5(4) . . . . ? O3 S1 C1 F2 62.0(4) . . . . ? O2 S1 C1 F2 -57.5(4) . . . . ? O4 S1 C1 F1 -59.5(4) . . . . ? O3 S1 C1 F1 -179.1(4) . . . . ? O2 S1 C1 F1 61.4(4) . . . . ? O4 S1 C1 F3 61.0(4) . . . . ? O3 S1 C1 F3 -58.6(4) . . . . ? O2 S1 C1 F3 -178.1(3) . . . . ? _geom_special_details ; Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) 0.6296 (0.0431) x + 12.1435 (0.0104) y - 10.1624 (0.0418) z = 1.7791 (0.0069) * 0.0044 (0.0033) C3 * -0.0031 (0.0034) C4 * -0.0015 (0.0034) C5 * 0.0048 (0.0033) C6 * -0.0035 (0.0032) C7 * -0.0011 (0.0031) C8 Rms deviation of fitted atoms = 0.0034 2.2341 (0.0673) x + 10.6264 (0.0251) y - 15.0057 (0.0622) z = 1.4861 (0.0103) Angle to previous plane (with approximate esd) = 12.77 ( 0.30 ) * 0.0031 (0.0022) C10 * -0.0032 (0.0023) C11 * 0.0031 (0.0022) C12 * -0.0031 (0.0022) C13 Rms deviation of fitted atoms = 0.0031 1.3699 (0.0429) x + 10.5426 (0.0152) y - 14.9469 (0.0373) z = 1.2238 (0.0163) Angle to previous plane (with approximate esd) = 2.27 ( 0.36 ) * -0.0055 (0.0033) C16 * 0.0084 (0.0033) C17 * 0.0001 (0.0033) C18 * -0.0115 (0.0033) C19 * 0.0144 (0.0032) C20 * -0.0060 (0.0032) C21 Rms deviation of fitted atoms = 0.0089 0.6296 (0.0431) x + 12.1435 (0.0104) y - 10.1624 (0.0418) z = 1.7791 (0.0069) Angle to previous plane (with approximate esd) = 13.09 ( 0.22 ) * 0.0044 (0.0033) C3 * -0.0031 (0.0034) C4 * -0.0015 (0.0034) C5 * 0.0048 (0.0033) C6 * -0.0035 (0.0032) C7 * -0.0011 (0.0031) C8 Rms deviation of fitted atoms = 0.0034 ; _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.878 _refine_diff_density_min -0.489 _refine_diff_density_rms 0.103 #========================================================== # END of CIF #==========================================================