# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2002 data_global _journal_coden_Cambridge 188 loop_ _publ_author_name _publ_author_address 'Kroulik, Jiri' ; Institute of Chemical Technology Prague Department of Organic Chemistry Technicka 5 166 28 Prague 6 CZECH REPUBLIC ; 'Cejka, Jan' ; Institute of Chemical Technology Prague Department of Solid State Chemistry Technicka 5 166 28 Prague 6 CZECH REPUBLIC ; 'Bohm, Stanislav' ; Institute of Chemical Technology Prague Department of Organic Chemistry Technicka 5 166 28 Prague 6 CZECH REPUBLIC ; 'Pavel, Sebek' ; BASF spol. s r.o. Safrankova 3 CZ - 150 00 Prague 5 CZECH REPUBLIC ; 'Nespurek, Stanislav' ; Institute of Macromolecular Chemistry Academy of Sciences of the Czech Republic 162 06 Prague 6 CZECH REPUBLIC ; 'Koshets, Igor' ; Institute of Macromolecular Chemistry Academy of Sciences of the Czech Republic 162 06 Prague 6 CZECH REPUBLIC ; 'Sedmera, Petr' ; Institute of Microbiology' Academy of Sciences of the Czech Republic 142 20 Prague 4 CZECH REPUBLIC ; 'Halada, Petr' ; Institute of Microbiology Academy of Sciences of the Czech Republic 142 20 Prague 4 CZECH REPUBLIC ; 'Havlicek, Vladimir' ; Institute of Microbiology Academy of Sciences of the Czech Republic 142 20 Prague 4 CZECH REPUBLIC ; 'Kratochvil, Bohumil' ; Institute of Chemical Technology Prague Department of Solid State Chemistry Technicka 5 166 28 Prague 6 CZECH REPUBLIC ; 'Kuthan, Josef' ; Institute of Chemical Technology Prague Department of Organic Chemistry Technicka 5 166 28 Prague 6 CZECH REPUBLIC ; _publ_contact_letter ; Please consider this CIF submission for publication as a Short Format Paper in .................... The figures have been sent by mail. ; _publ_contact_author_name 'Jiri Kroulik' _publ_contact_author_address ; Institute of Chemical Technology Prague Department of Organic Chemistry Technicka 5 166 28 Prague 6 CZECH REPUBLIC ; _publ_contact_author_phone ' 042 02 24354067 ' _publ_contact_author_fax ' 042 02 24311082 ' _publ_contact_author_email ' Jiri.Kroulik@vscht.cz ' _publ_requested_journal ? _publ_requested_category CO # choose from: FI FM FO CI CM CO AD# _publ_requested_coeditor_name ' ' _publ_requested_journal 'Perkin Transactions 2' _publ_section_title ; Substituted 2,4,4,6-Tetraphenyl-4H-Selenopyrans: Preparation, Reactivity, Photocolouration, X-ray and Quantum Calculation Conformational Study ; data_CRYSTALS_cif _database_code_CSD 185124 _diffrn_measurement_device_type ' Enraf-nonius CAD4 ' _diffrn_radiation_monochromator graphite _computing_data_collection 'CAD-4 software (Enraf-Nonius, 1989)' _computing_data_reduction ; RC93 (Watkin, D.J., Prout, C.K., Lilley, P.M.deQ. 1994) ; _computing_cell_refinement 'CAD-4 software (Enraf-Nonius, 1989)' # end_choice #========================================================================== # General computing #========================================================================== _computing_structure_refinement ; CRYSTALS Issue 10 (Watkin, Prout, Carruthers & Betteridge, 1996) ; _computing_publication_material ; CRYSTALS Issue 10 (Watkin, Prout, Carruthers & Betteridge, 1996) ; _computing_molecular_graphics ; CAMERON (Watkin, Prout & Pearce, 1996) ; # choose one of the following two lines # _computing_structure_solution 'SHELXS86 (Sheldrick, 1986)' _computing_structure_solution 'SIR92 (Giacovazzo et al, 1992)' #========================================================================== _chemical_name_systematic # IUPAC name, in full ; '2,6-Bis(4-bromophenyl)-4,4,-diphenyl-4H-selenopyran' ; _chemical_melting_point 167-169 # choose from 'full, fullcycle, atomblock, userblock, diagonal, sparse' _refine_ls_matrix_type full # choose from 'heavy, direct, difmap, geom' _atom_sites_solution_primary direct # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom # choose from 'none, undef, noref, refall, refxyz, refU, constr, mixed' _refine_ls_hydrogen_treatment noref #**************************************************************************** _cell_length_a 12.047(1) _cell_length_b 12.814(2) _cell_length_c 16.307(1) _cell_angle_alpha 90 _cell_angle_beta 105.510(6) _cell_angle_gamma 90 _cell_volume 2425.7 _symmetry_cell_setting 'Monoclinic ' _symmetry_space_group_name_H-M 'P 1 21/n 1 ' loop_ _symmetry_equiv_pos_as_xyz 'x,y,z' '-x,-y,-z' '-x+1/2,y+1/2,-z+1/2' 'x+1/2,-y+1/2,z+1/2' loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source 'C ' 0.0170 0.0090 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International_Tables_Vol_IV_Table_2.2B' 'H ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7997 0.0030 'International_Tables_Vol_IV_Table_2.2B' 'Br ' -0.7670 1.2830 17.1789 2.1723 5.2358 16.5796 5.6377 0.2609 3.9851 41.4328 2.9557 'International_Tables_Vol_IV_Table_2.2B' 'Se ' -0.8790 1.1390 17.0006 2.4098 5.8196 0.2726 3.9731 15.2372 4.3543 43.8163 2.8409 'International_Tables_Vol_IV_Table_2.2B' _chemical_formula_sum ' C29 H20 Br2 Se1 ' _chemical_formula_moiety ' C29 H20 Br2 Se1 ' _chemical_compound_source ; ? ; _chemical_formula_weight 607.25 _cell_measurement_reflns_used 20 _cell_measurement_theta_min 38 _cell_measurement_theta_max 40 _cell_measurement_temperature 293 _cell_formula_units_Z 4 _exptl_crystal_description ' needle ' _exptl_crystal_colour ' colourless ' _exptl_crystal_size_min 0.17 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_max 1.12 _exptl_crystal_density_diffrn 1.66 _exptl_crystal_density_meas 'not measured' _exptl_crystal_F_000 1184.23 _exptl_absorpt_coefficient_mu 6.06 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details '\y scan,(North et al, 1968)' _exptl_absorpt_correction_T_min 0.20 _exptl_absorpt_correction_T_max 0.35 # Sheldrick geometric definitions 0.35 0.35 _diffrn_standards_interval_time 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 2 _diffrn_standards_decay_% 1.19 _diffrn_ambient_temperature 293 _diffrn_reflns_number 7490 _reflns_number_total 3608 _diffrn_reflns_av_R_equivalents 0.04 # Number of reflections with Friedels Law is 3608 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 3601 _diffrn_measured_fraction_theta_max 1.000 _reflns_number_gt 3357 _diffrn_reflns_theta_min 0.00 _diffrn_reflns_theta_max 60.00 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _reflns_limit_h_min -13 _reflns_limit_h_max 13 _reflns_limit_k_min 0 _reflns_limit_k_max 14 _reflns_limit_l_min 0 _reflns_limit_l_max 18 _refine_diff_density_min -3.05 _refine_diff_density_max 0.80 _reflns_threshold_expression >1.96\s(I) _refine_ls_number_reflns 3357 _refine_ls_number_parameters 289 _refine_ls_R_factor_gt 0.0943 _refine_ls_wR_factor_ref 0.0698 _refine_ls_goodness_of_fit_ref 1.0697 _refine_ls_shift/su_max 0.000969 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Chebychev polynomial with 4 parameters, Carruthers & Watkin , 1979, 17.6 21.9 16.4 5.44 ; _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54180 _diffrn_measurement_method \w/2\q # Uequiv = arithmetic mean of Ui # i.e. Ueqiv = (U1+U2+U3)/3 loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type Se1 0.81601(3) 0.12653(3) 0.76992(3) 0.0496 1.0000 Uani Br1 0.98802(5) -0.39048(4) 0.67680(4) 0.0805 1.0000 Uani Br2 0.78319(6) 0.46866(4) 1.11636(3) 0.0823 1.0000 Uani C2 0.9243(3) 0.0828(2) 0.71006(19) 0.0398 1.0000 Uani C3 0.9783(3) 0.1522(3) 0.6746(2) 0.0434 1.0000 Uani C4 0.9531(3) 0.2688(3) 0.66873(19) 0.0379 1.0000 Uani C5 0.9402(3) 0.3081(2) 0.75441(19) 0.0396 1.0000 Uani C6 0.8804(2) 0.2618(2) 0.8018(2) 0.0396 1.0000 Uani C7 0.9387(2) -0.0314(2) 0.7041(2) 0.0411 1.0000 Uani C8 0.9365(3) -0.0990(3) 0.7703(2) 0.0478 1.0000 Uani C9 0.9508(3) -0.2066(3) 0.7632(3) 0.0530 1.0000 Uani C10 0.9669(3) -0.2464(3) 0.6885(2) 0.0533 1.0000 Uani C11 0.9676(3) -0.1808(3) 0.6209(2) 0.0557 1.0000 Uani C12 0.9523(3) -0.0744(3) 0.6289(2) 0.0510 1.0000 Uani C13 1.0573(3) 0.3249(2) 0.6521(2) 0.0389 1.0000 Uani C14 1.0535(3) 0.3782(3) 0.5761(2) 0.0464 1.0000 Uani C15 1.1496(3) 0.4312(3) 0.5674(3) 0.0606 1.0000 Uani C16 1.2499(3) 0.4330(3) 0.6318(3) 0.0578 1.0000 Uani C17 1.2553(3) 0.3791(4) 0.7044(3) 0.0603 1.0000 Uani C18 1.1610(3) 0.3244(3) 0.7143(2) 0.0540 1.0000 Uani C19 0.8419(3) 0.2922(3) 0.5990(2) 0.0418 1.0000 Uani C20 0.8027(4) 0.2266(3) 0.5286(2) 0.0635 1.0000 Uani C21 0.7049(4) 0.2509(4) 0.4660(3) 0.0769 1.0000 Uani C22 0.6415(3) 0.3385(4) 0.4692(3) 0.0647 1.0000 Uani C23 0.6791(3) 0.4049(3) 0.5388(3) 0.0593 1.0000 Uani C24 0.7766(3) 0.3812(3) 0.6019(2) 0.0486 1.0000 Uani C25 0.8599(2) 0.3095(3) 0.8790(2) 0.0409 1.0000 Uani C26 0.8636(3) 0.4168(3) 0.8887(2) 0.0483 1.0000 Uani C27 0.8454(3) 0.4651(3) 0.9598(2) 0.0519 1.0000 Uani C28 0.8198(3) 0.4036(3) 1.0220(2) 0.0510 1.0000 Uani C29 0.8143(4) 0.2970(3) 1.0152(2) 0.0609 1.0000 Uani C30 0.8343(3) 0.2504(3) 0.9434(2) 0.0527 1.0000 Uani H31 1.0403 0.1261 0.6496 0.0527 1.0000 Uiso H51 0.9807 0.3745 0.77681 0.0461 1.0000 Uiso H81 0.9240 -0.0702 0.8241 0.0551 1.0000 Uiso H91 0.9499 -0.2543 0.8116 0.0602 1.0000 Uiso H111 0.9792 -0.2102 0.5670 0.0627 1.0000 Uiso H121 0.9511 -0.0276 0.5796 0.0590 1.0000 Uiso H141 0.9811 0.3779 0.5286 0.0549 1.0000 Uiso H151 1.1458 0.4686 0.5129 0.0716 1.0000 Uiso H161 1.3181 0.4735 0.6254 0.0689 1.0000 Uiso H171 1.3284 0.3785 0.7512 0.0684 1.0000 Uiso H181 1.1675 0.2838 0.7677 0.0620 1.0000 Uiso H201 0.8467 0.1617 0.5238 0.0673 1.0000 Uiso H211 0.6792 0.2028 0.4162 0.0804 1.0000 Uiso H221 0.5700 0.3544 0.4232 0.0722 1.0000 Uiso H231 0.6352 0.4701 0.5425 0.0701 1.0000 Uiso H241 0.8014 0.4292 0.6518 0.0569 1.0000 Uiso H261 0.8801 0.4612 0.8429 0.0570 1.0000 Uiso H271 0.8513 0.5426 0.9665 0.0610 1.0000 Uiso H291 0.7967 0.2537 1.0612 0.0706 1.0000 Uiso H301 0.8298 0.1727 0.9378 0.0609 1.0000 Uiso 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 0.0487(3) 0.0382(3) 0.0693(3) -0.00848(16) 0.02864(19) -0.00595(14) Br1 0.1010(4) 0.0352(3) 0.1015(4) -0.0060(2) 0.0205(3) 0.0081(2) Br2 0.1277(5) 0.0744(4) 0.0573(3) -0.0127(2) 0.0464(3) -0.0012(3) C2 0.0431(15) 0.0325(17) 0.0436(16) -0.0006(13) 0.0115(12) 0.0002(12) C3 0.0473(16) 0.0379(19) 0.0468(17) -0.0027(13) 0.0156(13) 0.0012(13) C4 0.0435(15) 0.0320(17) 0.0406(16) -0.0010(12) 0.0156(12) 0.0025(12) C5 0.0435(15) 0.0328(16) 0.0422(16) -0.0021(13) 0.0111(13) -0.0020(12) C6 0.0410(15) 0.0345(17) 0.0440(16) 0.0007(12) 0.0127(12) 0.0044(12) C7 0.0351(14) 0.0330(17) 0.0542(18) -0.0020(14) 0.0102(12) 0.0009(11) C8 0.0498(18) 0.0376(18) 0.0585(19) -0.0008(15) 0.0189(14) -0.0037(14) C9 0.0531(18) 0.0363(18) 0.067(2) 0.0075(16) 0.0118(16) -0.0016(15) C10 0.0485(17) 0.0397(19) 0.068(2) -0.0065(17) 0.0084(15) -0.0007(14) C11 0.064(2) 0.040(2) 0.060(2) -0.0101(16) 0.0113(16) 0.0081(15) C12 0.0556(19) 0.047(2) 0.0501(18) -0.0004(15) 0.0127(14) 0.0005(15) C13 0.0427(15) 0.0324(16) 0.0431(16) -0.0033(13) 0.0143(13) -0.0003(12) C14 0.0482(17) 0.0424(19) 0.0505(18) 0.0095(14) 0.0167(14) 0.0063(13) C15 0.062(2) 0.056(2) 0.068(2) 0.0209(18) 0.0248(18) 0.0034(17) C16 0.0485(18) 0.049(2) 0.082(3) -0.0030(18) 0.0267(18) -0.0066(16) C17 0.0440(18) 0.073(3) 0.062(2) -0.0133(19) 0.0122(16) -0.0045(16) C18 0.0515(19) 0.065(2) 0.0459(18) 0.0012(16) 0.0129(15) -0.0062(17) C19 0.0484(16) 0.0376(17) 0.0404(16) -0.0007(13) 0.0138(13) -0.0077(13) C20 0.088(3) 0.043(2) 0.051(2) -0.0084(15) 0.0051(19) 0.0024(18) C21 0.098(3) 0.063(3) 0.053(2) -0.0062(19) -0.011(2) -0.015(2) C22 0.060(2) 0.068(3) 0.055(2) 0.0153(19) -0.0040(17) -0.016(2) C23 0.056(2) 0.061(2) 0.062(2) 0.0121(18) 0.0179(17) 0.0086(17) C24 0.0487(18) 0.050(2) 0.0469(17) -0.0061(14) 0.0124(14) 0.0025(14) C25 0.0381(14) 0.0417(18) 0.0421(16) 0.0013(13) 0.0092(12) 0.0024(12) C26 0.0602(19) 0.0404(19) 0.0476(18) 0.0057(14) 0.0202(15) 0.0032(14) C27 0.070(2) 0.0346(18) 0.0534(19) 0.0013(15) 0.0203(16) 0.0010(15) C28 0.0562(19) 0.053(2) 0.0444(17) -0.0031(15) 0.0149(14) 0.0030(16) C29 0.080(2) 0.062(3) 0.0473(19) 0.0095(18) 0.0297(17) -0.002(2) C30 0.075(2) 0.0333(18) 0.055(2) 0.0042(15) 0.0267(17) 0.0025(15) _refine_ls_extinction_method 'None' loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Se1 . C2 . 1.911(3) yes Se1 . C6 . 1.914(3) yes Br1 . C10 . 1.880(4) yes Br2 . C28 . 1.903(4) yes C2 . C3 . 1.323(5) yes C2 . C7 . 1.480(5) yes C3 . C4 . 1.523(5) yes C3 . H31 . 1.000 no C4 . C5 . 1.531(4) yes C4 . C13 . 1.532(4) yes C4 . C19 . 1.536(4) yes C5 . C6 . 1.329(4) yes C5 . H51 . 1.000 no C6 . C25 . 1.478(4) yes C7 . C8 . 1.391(5) yes C7 . C12 . 1.393(5) yes C8 . C9 . 1.398(5) yes C8 . H81 . 1.000 no C9 . C10 . 1.382(6) yes C9 . H91 . 1.000 no C10 . C11 . 1.388(6) yes C11 . C12 . 1.386(6) yes C11 . H111 . 1.000 no C12 . H121 . 1.000 no C13 . C14 . 1.404(5) yes C13 . C18 . 1.383(5) yes C14 . C15 . 1.383(5) yes C14 . H141 . 1.000 no C15 . C16 . 1.373(6) yes C15 . H151 . 1.000 no C16 . C17 . 1.357(6) yes C16 . H161 . 1.000 no C17 . C18 . 1.380(6) yes C17 . H171 . 1.000 no C18 . H181 . 1.000 no C19 . C20 . 1.399(5) yes C19 . C24 . 1.394(5) yes C20 . C21 . 1.373(6) yes C20 . H201 . 1.000 no C21 . C22 . 1.367(8) yes C21 . H211 . 1.000 no C22 . C23 . 1.394(6) yes C22 . H221 . 1.000 no C23 . C24 . 1.373(5) yes C23 . H231 . 1.000 no C24 . H241 . 1.000 no C25 . C26 . 1.384(5) yes C25 . C30 . 1.393(5) yes C26 . C27 . 1.382(5) yes C26 . H261 . 1.000 no C27 . C28 . 1.382(5) yes C27 . H271 . 1.000 no C28 . C29 . 1.370(6) yes C29 . C30 . 1.392(5) yes C29 . H291 . 1.000 no C30 . H301 . 1.000 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C2 . Se1 . C6 . 97.00(13) yes Se1 . C2 . C3 . 120.6(2) yes Se1 . C2 . C7 . 115.6(2) yes C3 . C2 . C7 . 123.8(3) yes C2 . C3 . C4 . 125.1(3) yes C2 . C3 . H31 . 117.5(2) no C4 . C3 . H31 . 117.49(16) no C3 . C4 . C5 . 109.4(3) yes C3 . C4 . C13 . 108.2(2) yes C5 . C4 . C13 . 107.1(2) yes C3 . C4 . C19 . 111.0(3) yes C5 . C4 . C19 . 109.3(2) yes C13 . C4 . C19 . 111.8(2) yes C4 . C5 . C6 . 125.9(3) yes C4 . C5 . H51 . 117.03(17) no C6 . C5 . H51 . 117.04(19) no Se1 . C6 . C5 . 119.3(2) yes Se1 . C6 . C25 . 117.2(2) yes C5 . C6 . C25 . 123.5(3) yes C2 . C7 . C8 . 122.5(3) yes C2 . C7 . C12 . 119.5(3) yes C8 . C7 . C12 . 117.9(3) yes C7 . C8 . C9 . 121.4(3) yes C7 . C8 . H81 . 119.39(19) no C9 . C8 . H81 . 119.2(2) no C8 . C9 . C10 . 119.1(3) yes C8 . C9 . H91 . 120.7(2) no C10 . C9 . H91 . 120.2(2) no Br1 . C10 . C9 . 120.5(3) yes Br1 . C10 . C11 . 118.9(3) yes C9 . C10 . C11 . 120.6(3) yes C10 . C11 . C12 . 119.4(3) yes C10 . C11 . H111 . 120.2(2) no C12 . C11 . H111 . 120.4(2) no C7 . C12 . C11 . 121.4(3) yes C7 . C12 . H121 . 119.3(2) no C11 . C12 . H121 . 119.3(2) no C4 . C13 . C14 . 123.3(3) yes C4 . C13 . C18 . 119.4(3) yes C14 . C13 . C18 . 117.3(3) yes C13 . C14 . C15 . 120.0(3) yes C13 . C14 . H141 . 119.80(19) no C15 . C14 . H141 . 120.2(2) no C14 . C15 . C16 . 121.3(4) yes C14 . C15 . H151 . 119.1(2) no C16 . C15 . H151 . 119.6(2) no C15 . C16 . C17 . 119.0(3) yes C15 . C16 . H161 . 120.5(2) no C17 . C16 . H161 . 120.4(2) no C16 . C17 . C18 . 120.8(3) yes C16 . C17 . H171 . 119.7(2) no C18 . C17 . H171 . 119.5(2) no C13 . C18 . C17 . 121.5(4) yes C13 . C18 . H181 . 119.1(2) no C17 . C18 . H181 . 119.4(2) no C4 . C19 . C20 . 121.8(3) yes C4 . C19 . C24 . 121.5(3) yes C20 . C19 . C24 . 116.7(3) yes C19 . C20 . C21 . 120.6(4) yes C19 . C20 . H201 . 119.6(2) no C21 . C20 . H201 . 119.8(3) no C20 . C21 . C22 . 122.4(4) yes C20 . C21 . H211 . 118.8(3) no C22 . C21 . H211 . 118.8(2) no C21 . C22 . C23 . 118.0(4) yes C21 . C22 . H221 . 121.2(2) no C23 . C22 . H221 . 120.8(2) no C22 . C23 . C24 . 120.1(4) yes C22 . C23 . H231 . 119.8(2) no C24 . C23 . H231 . 120.0(2) no C19 . C24 . C23 . 122.3(3) yes C19 . C24 . H241 . 118.82(19) no C23 . C24 . H241 . 118.9(2) no C6 . C25 . C26 . 120.0(3) yes C6 . C25 . C30 . 122.6(3) yes C26 . C25 . C30 . 117.4(3) yes C25 . C26 . C27 . 122.2(3) yes C25 . C26 . H261 . 119.09(19) no C27 . C26 . H261 . 118.7(2) no C26 . C27 . C28 . 118.4(3) yes C26 . C27 . H271 . 120.9(2) no C28 . C27 . H271 . 120.7(2) no Br2 . C28 . C27 . 119.2(3) yes Br2 . C28 . C29 . 119.0(3) yes C27 . C28 . C29 . 121.7(3) yes C28 . C29 . C30 . 118.6(3) yes C28 . C29 . H291 . 120.5(2) no C30 . C29 . H291 . 120.8(2) no C25 . C30 . C29 . 121.6(3) yes C25 . C30 . H301 . 119.4(2) no C29 . C30 . H301 . 119.0(2) no data_CRYSTALS_cif2 _database_code_CSD 185125 _audit_creation_date 02-22-08 _audit_creation_method CRYSTALS_ver_12-03-99 _diffrn_measurement_device_type ' Enraf-nonius CAD4 ' _diffrn_radiation_monochromator graphite _computing_data_collection 'CAD-4 software (Enraf-Nonius, 1989)' _computing_data_reduction ; RC93 (Watkin, D.J., Prout, C.K., Lilley, P.M.deQ. 1994) ; _computing_cell_refinement 'CAD-4 software (Enraf-Nonius, 1989)' # end_choice #========================================================================== # General computing #========================================================================== _computing_structure_refinement ; CRYSTALS Issue 10 (Watkin, Prout, Carruthers & Betteridge, 1996) ; _computing_publication_material ; CRYSTALS Issue 10 (Watkin, Prout, Carruthers & Betteridge, 1996) ; _computing_molecular_graphics ; CAMERON (Watkin, Prout & Pearce, 1996) ; # choose one of the following two lines # _computing_structure_solution 'SHELXS86 (Sheldrick, 1986)' _computing_structure_solution 'SIR92 (Giacovazzo et al, 1992)' #========================================================================== _chemical_name_systematic # IUPAC name, in full ; '2,4,4,6-tetraphenyl-4H-selenopyran' ; _chemical_melting_point 138-140 # choose from 'full, fullcycle, atomblock, userblock, diagonal, sparse' _refine_ls_matrix_type full # choose from 'heavy, direct, difmap, geom' _atom_sites_solution_primary direct # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom # choose from 'none, undef, noref, refall, refxyz, refU, constr, mixed' _refine_ls_hydrogen_treatment refall #**************************************************************************** _cell_length_a 18.117(3) _cell_angle_alpha 90 _cell_length_b 7.088(1) _cell_angle_beta 90 _cell_length_c 34.009(7) _cell_angle_gamma 90 _cell_volume 4367.0 _symmetry_cell_setting 'Orthorhombic ' _symmetry_space_group_name_H-M 'P n a 21 ' loop_ _symmetry_equiv_pos_as_xyz 'x,y,z' '-x+1/2,y+1/2,z+1/2' 'x+1/2,-y+1/2,z' '-x,-y,z+1/2' loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source 'C ' 0.0170 0.0090 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International_Tables_Vol_IV_Table_2.2B' 'H ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7997 0.0030 'International_Tables_Vol_IV_Table_2.2B' 'Se ' -0.8790 1.1390 17.0006 2.4098 5.8196 0.2726 3.9731 15.2372 4.3543 43.8163 2.8409 'International_Tables_Vol_IV_Table_2.2B' _chemical_formula_sum ' C29 H22 Se1 ' _chemical_formula_moiety ' C29 H22 Se1 ' _chemical_compound_source ; ? ; _chemical_formula_weight 449.45 _cell_measurement_reflns_used 23 _cell_measurement_theta_min 38 _cell_measurement_theta_max 40 _cell_measurement_temperature 293 _cell_formula_units_Z 8 _exptl_crystal_description ' block ' _exptl_crystal_colour ' colourless ' _exptl_crystal_size_min 0.14 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_max 0.53 _exptl_crystal_density_diffrn 1.37 _exptl_crystal_density_meas 'not measured' _exptl_crystal_F_000 1836.66 _exptl_absorpt_coefficient_mu 2.40 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details '\y scan,(North et al, 1968)' _exptl_absorpt_correction_T_min 0.51 _exptl_absorpt_correction_T_max 0.71 # Sheldrick geometric definitions 0.51 0.71 _diffrn_standards_interval_time 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 2 _diffrn_standards_decay_% 2.76 _diffrn_ambient_temperature 293 _diffrn_reflns_number 9314 _reflns_number_total 8281 _diffrn_reflns_av_R_equivalents 0.01 # Number of reflections with Friedels Law is 8284 # Number of reflections without Friedels Law is 8281 # Theoretical number of reflections is about 4671 _diffrn_measured_fraction_theta_max 1.000 _reflns_number_gt 7769 _diffrn_reflns_theta_min 0.00 _diffrn_reflns_theta_max 78.00 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -42 _diffrn_reflns_limit_l_max 41 _reflns_limit_h_min 0 _reflns_limit_h_max 22 _reflns_limit_k_min 0 _reflns_limit_k_max 8 _reflns_limit_l_min -42 _reflns_limit_l_max 41 _refine_diff_density_min -3.29 _refine_diff_density_max 0.88 _reflns_threshold_expression >1.96\s(I) _refine_ls_number_reflns 7769 _refine_ls_number_parameters 718 _refine_ls_R_factor_gt 0.0621 _refine_ls_wR_factor_ref 0.0529 _refine_ls_goodness_of_fit_ref 1.0400 _refine_ls_shift/su_max 0.002258 _refine_ls_abs_structure_Flack '0.288(15)' _refine_ls_abs_structure_details 'Flack, 0 Friedel-pairs' _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Chebychev polynomial with 5 parameters, Carruthers & Watkin , 1979, 6.64 7.61 6.81 2.15 0.963 ; _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54180 _diffrn_measurement_method \w/2\q # Uequiv = arithmetic mean of Ui # i.e. Ueqiv = (U1+U2+U3)/3 loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type Se1 0.42436(2) 0.40734(5) 0.39802(3) 0.0518 1.0000 Uani Se51 0.20865(2) 0.40469(5) 0.26677(3) 0.0564 1.0000 Uani C2 0.39355(17) 0.2511(4) 0.44008(9) 0.0409 1.0000 Uani C3 0.42399(19) 0.2574(5) 0.47595(11) 0.0472 1.0000 Uani C4 0.48995(18) 0.3693(4) 0.49073(9) 0.0403 1.0000 Uani C5 0.51631(17) 0.5194(4) 0.46237(9) 0.0409 1.0000 Uani C6 0.49561(17) 0.5531(4) 0.42558(9) 0.0389 1.0000 Uani C56 0.17889(17) 0.2503(5) 0.2239(1) 0.0429 1.0000 Uani C55 0.20963(19) 0.2565(6) 0.18868(11) 0.0495 1.0000 Uani C54 0.27608(18) 0.3674(5) 0.17415(9) 0.0426 1.0000 Uani C53 0.30151(18) 0.5180(5) 0.2031(1) 0.0433 1.0000 Uani C52 0.28065(17) 0.5520(4) 0.2400(1) 0.0394 1.0000 Uani C7 0.33453(18) 0.1173(5) 0.42978(11) 0.0466 1.0000 Uani C8 0.2762(2) 0.1676(6) 0.40493(13) 0.0576 1.0000 Uani C9 0.2224(2) 0.0371(7) 0.39582(17) 0.0711 1.0000 Uani C10 0.2239(2) -0.1422(7) 0.41126(16) 0.0727 1.0000 Uani C11 0.2806(2) -0.1930(7) 0.43518(15) 0.0679 1.0000 Uani C12 0.3361(2) -0.0658(6) 0.44467(13) 0.0589 1.0000 Uani C25 0.52730(15) 0.7074(4) 0.40103(9) 0.0375 1.0000 Uani C26 0.53817(19) 0.8858(4) 0.41745(11) 0.0446 1.0000 Uani C27 0.5696(2) 1.0299(5) 0.39503(12) 0.0541 1.0000 Uani C28 0.5897(3) 0.9964(6) 0.35672(12) 0.0612 1.0000 Uani C29 0.5796(2) 0.8193(7) 0.34003(11) 0.0625 1.0000 Uani C30 0.54746(19) 0.6754(6) 0.3620(1) 0.0495 1.0000 Uani C75 0.11807(17) 0.1214(5) 0.23416(11) 0.0460 1.0000 Uani C80 0.0595(2) 0.1726(7) 0.25826(12) 0.0535 1.0000 Uani C79 0.0034(2) 0.0458(7) 0.26678(16) 0.0669 1.0000 Uani C78 0.0049(2) -0.1335(7) 0.25190(15) 0.0702 1.0000 Uani C77 0.0634(3) -0.1904(7) 0.22767(16) 0.0734 1.0000 Uani C76 0.1200(2) -0.0649(5) 0.21983(14) 0.0585 1.0000 Uani C57 0.31082(15) 0.7038(4) 0.2647(1) 0.0395 1.0000 Uani C62 0.32541(19) 0.8817(5) 0.2491(1) 0.0447 1.0000 Uani C61 0.3556(2) 1.0236(5) 0.27227(12) 0.0569 1.0000 Uani C60 0.3718(2) 0.9908(6) 0.31132(12) 0.0604 1.0000 Uani C59 0.3566(2) 0.8170(6) 0.32736(11) 0.0599 1.0000 Uani C58 0.3256(2) 0.6756(6) 0.3047(1) 0.0501 1.0000 Uani C19 0.55145(18) 0.2260(4) 0.4997(1) 0.0407 1.0000 Uani C20 0.5383(3) 0.0733(5) 0.52490(12) 0.0545 1.0000 Uani C21 0.5931(3) -0.0600(5) 0.53178(13) 0.0663 1.0000 Uani C22 0.6614(3) -0.0429(7) 0.51503(15) 0.0714 1.0000 Uani C23 0.6751(3) 0.1046(6) 0.49003(15) 0.0654 1.0000 Uani C24 0.6215(2) 0.2391(6) 0.4827(1) 0.0508 1.0000 Uani C13 0.46674(18) 0.4752(4) 0.5286(1) 0.0432 1.0000 Uani C18 0.4037(3) 0.5880(5) 0.52739(15) 0.0599 1.0000 Uani C17 0.3834(3) 0.6943(7) 0.56001(18) 0.0770 1.0000 Uani C16 0.4253(3) 0.6902(7) 0.59380(16) 0.0748 1.0000 Uani C15 0.4863(3) 0.5792(6) 0.59549(13) 0.0648 1.0000 Uani C14 0.5076(2) 0.4732(6) 0.5629(1) 0.0508 1.0000 Uani C69 0.33787(19) 0.2246(4) 0.16557(9) 0.0423 1.0000 Uani C74 0.3238(2) 0.0731(5) 0.14028(11) 0.0506 1.0000 Uani C73 0.3777(3) -0.0609(5) 0.13252(13) 0.0633 1.0000 Uani C72 0.4463(3) -0.0472(6) 0.15001(14) 0.0673 1.0000 Uani C71 0.4612(3) 0.1032(6) 0.17475(13) 0.0623 1.0000 Uani C70 0.4067(2) 0.2376(5) 0.1824(1) 0.0476 1.0000 Uani C63 0.25285(19) 0.4768(5) 0.1366(1) 0.0426 1.0000 Uani C68 0.1904(2) 0.5901(6) 0.13750(16) 0.0629 1.0000 Uani C67 0.1691(3) 0.6944(6) 0.10536(19) 0.0779 1.0000 Uani C66 0.2100(3) 0.6908(7) 0.07138(18) 0.0768 1.0000 Uani C65 0.2736(3) 0.5781(7) 0.06948(14) 0.0667 1.0000 Uani C64 0.2945(2) 0.4712(6) 0.1019(1) 0.0510 1.0000 Uani H31 0.3948(19) 0.177(5) 0.498(1) 0.036(8) 1.0000 Uiso H531 0.341(3) 0.571(7) 0.1951(17) 0.068(14) 1.0000 Uiso H51 0.546(3) 0.624(7) 0.4709(17) 0.071(14) 1.0000 Uiso H271 0.577(3) 1.156(9) 0.4111(17) 0.081(16) 1.0000 Uiso H261 0.518(2) 0.906(4) 0.4433(12) 0.039(9) 1.0000 Uiso H701 0.419(2) 0.329(7) 0.2003(15) 0.057(11) 1.0000 Uiso H551 0.201(2) 0.182(6) 0.1717(13) 0.04(1) 1.0000 Uiso H801 0.059(2) 0.270(6) 0.2696(13) 0.04(1) 1.0000 Uiso H621 0.3257(18) 0.884(4) 0.2201(11) 0.030(7) 1.0000 Uiso H81 0.274(2) 0.301(6) 0.3923(13) 0.051(9) 1.0000 Uiso H281 0.617(3) 1.057(8) 0.3421(18) 0.076(15) 1.0000 Uiso H201 0.488(3) 0.055(6) 0.5354(14) 0.057(11) 1.0000 Uiso H291 0.581(2) 0.791(7) 0.3145(16) 0.058(11) 1.0000 Uiso H581 0.303(3) 0.590(9) 0.315(2) 0.081(18) 1.0000 Uiso H741 0.278(3) 0.065(6) 0.1277(17) 0.062(13) 1.0000 Uiso H241 0.628(2) 0.340(7) 0.4645(14) 0.05(1) 1.0000 Uiso H641 0.343(3) 0.380(8) 0.1018(19) 0.079(16) 1.0000 Uiso H301 0.539(2) 0.554(6) 0.3474(14) 0.05(1) 1.0000 Uiso H611 0.358(3) 1.161(8) 0.2620(17) 0.076(14) 1.0000 Uiso H171 0.341(4) 0.77(1) 0.5525(19) 0.096(19) 1.0000 Uiso H181 0.372(3) 0.589(6) 0.5072(16) 0.053(11) 1.0000 Uiso H681 0.159(3) 0.588(6) 0.1645(15) 0.059(12) 1.0000 Uiso H791 -0.030(3) 0.096(5) 0.2838(14) 0.051(11) 1.0000 Uiso H141 0.542(2) 0.403(5) 0.5622(13) 0.04(1) 1.0000 Uiso H91 0.189(3) 0.079(8) 0.372(2) 0.088(18) 1.0000 Uiso H121 0.377(3) -0.108(7) 0.4627(19) 0.075(16) 1.0000 Uiso H111 0.286(3) -0.327(11) 0.448(2) 0.10(2) 1.0000 Uiso H721 0.479(3) -0.161(9) 0.1406(19) 0.093(17) 1.0000 Uiso H211 0.581(2) -0.145(7) 0.5517(14) 0.055(11) 1.0000 Uiso H781 -0.034(2) -0.209(7) 0.2590(14) 0.062(12) 1.0000 Uiso H731 0.362(3) -0.20(1) 0.1200(19) 0.100(18) 1.0000 Uiso H711 0.507(3) 0.097(6) 0.1847(16) 0.061(12) 1.0000 Uiso H161 0.420(3) 0.757(9) 0.6218(19) 0.092(18) 1.0000 Uiso H601 0.394(3) 1.100(8) 0.3283(19) 0.085(17) 1.0000 Uiso H101 0.179(3) -0.230(8) 0.4122(16) 0.083(17) 1.0000 Uiso H231 0.725(3) 0.137(8) 0.4776(17) 0.074(15) 1.0000 Uiso H591 0.368(3) 0.806(6) 0.3539(15) 0.059(11) 1.0000 Uiso H221 0.703(3) -0.134(8) 0.5178(19) 0.078(15) 1.0000 Uiso H661 0.200(3) 0.753(8) 0.0547(16) 0.067(14) 1.0000 Uiso H771 0.063(4) -0.333(12) 0.219(3) 0.12(2) 1.0000 Uiso H761 0.161(3) -0.109(7) 0.2028(19) 0.079(17) 1.0000 Uiso H671 0.119(3) 0.793(7) 0.1057(15) 0.065(13) 1.0000 Uiso H651 0.324(7) 0.566(15) 0.048(4) 0.18(4) 1.0000 Uiso H151 0.517(4) 0.567(9) 0.622(3) 0.11(2) 1.0000 Uiso 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 0.0636(2) 0.05010(18) 0.04155(17) 0.00511(16) -0.01297(14) -0.01648(14) Se51 0.0677(2) 0.0589(2) 0.04268(18) -0.00771(17) 0.01725(16) -0.02047(16) C2 0.0403(14) 0.0360(13) 0.0463(14) -0.0023(12) 0.0027(12) -0.0057(11) C3 0.0531(19) 0.0460(17) 0.0425(17) 0.0008(14) 0.0016(12) -0.0157(13) C4 0.0487(16) 0.0395(15) 0.0328(13) 0.0013(11) -0.0005(11) -0.0062(13) C5 0.0463(15) 0.0424(15) 0.0339(14) 0.0016(12) 0.0006(11) -0.0117(12) C6 0.0452(14) 0.0339(13) 0.0377(14) -0.0014(11) 0.0019(11) -0.0002(11) C56 0.0421(15) 0.0431(15) 0.0436(15) 0.0003(13) 0.0003(12) -0.0066(12) C55 0.054(2) 0.052(2) 0.0417(17) -0.0034(16) 0.0018(13) -0.0149(14) C54 0.0481(15) 0.0463(16) 0.0333(13) 0.0008(12) 0.0012(12) -0.0137(13) C53 0.0478(16) 0.0419(16) 0.0402(15) -0.0033(12) 0.0068(12) -0.0086(12) C52 0.0397(14) 0.0387(14) 0.0397(14) 0.0010(12) 0.0021(11) 0.0019(11) C7 0.0400(14) 0.0495(17) 0.0502(17) -0.0063(13) 0.0001(13) -0.0046(13) C8 0.0446(15) 0.055(2) 0.073(3) -0.0090(18) -0.0094(16) -0.0013(15) C9 0.0393(15) 0.084(3) 0.090(3) -0.011(3) -0.0143(19) -0.0049(17) C10 0.0482(19) 0.073(3) 0.097(3) -0.019(2) 0.007(2) -0.0208(18) C11 0.065(2) 0.061(2) 0.078(3) 0.002(2) 0.002(2) -0.023(2) C12 0.0539(18) 0.057(2) 0.066(2) 0.0103(17) -0.0035(17) -0.0184(16) C25 0.0358(11) 0.0439(13) 0.0328(12) 0.0061(12) -0.0014(11) 0.000(1) C26 0.0558(18) 0.0366(15) 0.0415(16) 0.0020(12) 0.0052(14) -0.0025(13) C27 0.073(2) 0.0397(14) 0.0497(17) 0.0070(16) 0.0035(16) -0.0067(14) C28 0.072(2) 0.064(2) 0.0473(17) 0.0154(17) -0.0025(16) -0.0192(19) C29 0.079(2) 0.078(3) 0.0305(15) 0.0034(15) 0.0041(15) -0.027(2) C30 0.0539(18) 0.0575(19) 0.0371(15) -0.0053(14) -0.0010(12) -0.0118(15) C75 0.0376(14) 0.0532(18) 0.0472(16) 0.0102(13) 0.0012(12) -0.0066(13) C80 0.0448(16) 0.062(2) 0.054(2) 0.0090(18) 0.0060(14) -0.0016(16) C79 0.0406(16) 0.086(3) 0.075(2) 0.025(2) 0.0058(19) -0.0017(17) C78 0.0469(19) 0.082(3) 0.082(3) 0.030(2) -0.0049(18) -0.0214(19) C77 0.065(2) 0.068(3) 0.087(3) 0.010(2) 0.002(2) -0.026(2) C76 0.0537(19) 0.054(2) 0.068(2) -0.0011(17) 0.0059(17) -0.0163(16) C57 0.0385(12) 0.0422(13) 0.0378(13) 0.0012(13) 0.0023(12) 0.0049(11) C62 0.0529(17) 0.0398(16) 0.0414(16) -0.0007(12) -0.0018(13) 0.0017(13) C61 0.070(2) 0.0436(16) 0.057(2) -0.0045(15) 0.0036(17) -0.0072(15) C60 0.068(2) 0.060(2) 0.0540(19) -0.0176(17) 0.0002(17) -0.0082(17) C59 0.076(2) 0.064(2) 0.0392(16) -0.0069(15) -0.0039(16) 0.0026(19) C58 0.063(2) 0.0486(18) 0.0384(16) 0.0008(14) -0.0003(13) -0.0015(16) C19 0.0519(16) 0.0365(14) 0.0338(14) -0.0054(11) 0.0006(12) -0.0021(12) C20 0.069(2) 0.0486(19) 0.0458(18) 0.0037(15) -0.0012(16) -0.0049(16) C21 0.100(3) 0.0416(18) 0.057(2) 0.0066(17) -0.009(2) -0.0006(19) C22 0.090(3) 0.055(2) 0.069(3) -0.002(2) -0.009(2) 0.019(2) C23 0.061(2) 0.068(2) 0.067(3) -0.0084(19) -0.0011(18) 0.0095(18) C24 0.060(2) 0.0510(18) 0.0416(16) -0.0035(15) 0.0003(14) -0.0017(15) C13 0.0498(16) 0.0359(13) 0.0439(15) -0.0019(12) 0.0075(12) -0.0054(12) C18 0.060(2) 0.051(2) 0.069(2) 0.0015(16) 0.000(2) 0.0049(15) C17 0.070(3) 0.060(3) 0.101(4) -0.013(2) 0.021(3) 0.012(2) C16 0.083(3) 0.067(3) 0.075(3) -0.027(2) 0.029(2) -0.009(2) C15 0.070(2) 0.074(3) 0.050(2) -0.0215(18) 0.0088(18) -0.0095(19) C14 0.0531(19) 0.0549(18) 0.0444(17) -0.0137(14) 0.0050(14) -0.0042(17) C69 0.0587(18) 0.0382(14) 0.0300(13) 0.0046(11) 0.0040(12) -0.0077(12) C74 0.064(2) 0.0418(16) 0.0459(17) -0.0015(13) -0.0017(16) -0.0052(14) C73 0.083(3) 0.0475(19) 0.060(2) -0.0063(16) 0.0084(19) -0.0006(17) C72 0.079(3) 0.054(2) 0.069(2) 0.0017(18) 0.006(2) 0.016(2) C71 0.066(2) 0.064(2) 0.056(2) 0.0041(17) -0.0057(18) 0.0120(17) C70 0.057(2) 0.0460(16) 0.0394(14) 0.0017(13) -0.0017(13) -0.0020(14) C63 0.0479(16) 0.0393(14) 0.0405(15) -0.0005(12) -0.0018(12) -0.0087(12) C68 0.060(2) 0.056(2) 0.073(3) 0.0003(18) 0.001(2) 0.0070(16) C67 0.064(2) 0.054(2) 0.115(4) 0.014(2) -0.015(3) 0.006(2) C66 0.083(3) 0.067(3) 0.081(3) 0.029(2) -0.028(3) -0.014(2) C65 0.072(2) 0.075(3) 0.053(2) 0.0170(18) -0.0070(19) -0.010(2) C64 0.0558(19) 0.0537(18) 0.0436(16) 0.0096(15) 0.0011(14) -0.0066(15) _refine_ls_extinction_method 'None' loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Se1 . C2 . 1.893(3) yes Se1 . C6 . 1.901(3) yes Se51 . C56 . 1.901(3) yes Se51 . C52 . 1.902(3) yes C2 . C3 . 1.340(5) yes C2 . C7 . 1.472(4) yes C3 . C4 . 1.520(4) yes C3 . H31 . 1.08(4) no C4 . C5 . 1.513(4) yes C4 . C19 . 1.538(5) yes C4 . C13 . 1.548(4) yes C5 . C6 . 1.328(4) yes C5 . H51 . 0.96(5) no C6 . C25 . 1.491(4) yes C56 . C55 . 1.321(5) yes C56 . C75 . 1.473(4) yes C55 . C54 . 1.520(4) yes C55 . H551 . 0.80(5) no C54 . C53 . 1.524(4) yes C54 . C69 . 1.537(5) yes C54 . C63 . 1.551(4) yes C53 . C52 . 1.333(5) yes C53 . H531 . 0.85(6) no C52 . C57 . 1.470(4) yes C7 . C8 . 1.399(5) yes C7 . C12 . 1.393(5) yes C8 . C9 . 1.380(6) yes C8 . H81 . 1.04(4) no C9 . C10 . 1.375(7) yes C9 . H91 . 1.06(7) no C10 . C11 . 1.360(7) yes C10 . H101 . 1.03(6) no C11 . C12 . 1.388(5) yes C11 . H111 . 1.05(8) no C12 . H121 . 1.01(6) no C25 . C26 . 1.397(4) yes C25 . C30 . 1.394(4) yes C26 . C27 . 1.396(5) yes C26 . H261 . 0.97(4) no C27 . C28 . 1.374(6) yes C27 . H271 . 1.05(6) no C28 . C29 . 1.390(7) yes C28 . H281 . 0.82(6) no C29 . C30 . 1.393(5) yes C29 . H291 . 0.89(5) no C30 . H301 . 1.01(4) no C75 . C80 . 1.389(5) yes C75 . C76 . 1.408(5) yes C80 . C79 . 1.388(6) yes C80 . H801 . 0.79(4) no C79 . C78 . 1.368(7) yes C79 . H791 . 0.91(5) no C78 . C77 . 1.403(8) yes C78 . H781 . 0.92(5) no C77 . C76 . 1.383(5) yes C77 . H771 . 1.05(9) no C76 . H761 . 1.00(6) no C57 . C62 . 1.394(4) yes C57 . C58 . 1.400(5) yes C62 . C61 . 1.391(5) yes C62 . H621 . 0.99(4) no C61 . C60 . 1.380(6) yes C61 . H611 . 1.03(6) no C60 . C59 . 1.375(6) yes C60 . H601 . 1.05(6) no C59 . C58 . 1.384(6) yes C59 . H591 . 0.93(5) no C58 . H581 . 0.80(6) no C19 . C20 . 1.401(5) yes C19 . C24 . 1.397(5) yes C20 . C21 . 1.391(6) yes C20 . H201 . 0.98(5) no C21 . C22 . 1.368(8) yes C21 . H211 . 0.93(5) no C22 . C23 . 1.370(7) yes C22 . H221 . 0.99(6) no C23 . C24 . 1.384(6) yes C23 . H231 . 1.03(6) no C24 . H241 . 0.95(5) no C13 . C18 . 1.395(6) yes C13 . C14 . 1.382(5) yes C18 . C17 . 1.390(7) yes C18 . H181 . 0.89(5) no C17 . C16 . 1.377(9) yes C17 . H171 . 0.98(7) no C16 . C15 . 1.358(7) yes C16 . H161 . 1.07(6) no C15 . C14 . 1.395(5) yes C15 . H151 . 1.06(9) no C14 . H141 . 0.79(4) no C69 . C74 . 1.399(5) yes C69 . C70 . 1.375(5) yes C74 . C73 . 1.388(6) yes C74 . H741 . 0.93(5) no C73 . C72 . 1.381(7) yes C73 . H731 . 1.09(7) no C72 . C71 . 1.384(7) yes C72 . H721 . 1.05(6) no C71 . C70 . 1.397(6) yes C71 . H711 . 0.90(5) no C70 . H701 . 0.91(5) no C63 . C68 . 1.388(6) yes C63 . C64 . 1.404(5) yes C68 . C67 . 1.375(7) yes C68 . H681 . 1.08(5) no C67 . C66 . 1.373(9) yes C67 . H671 . 1.14(5) no C66 . C65 . 1.403(8) yes C66 . H661 . 0.74(6) no C65 . C64 . 1.390(5) yes C65 . H651 . 1.16(13) no C64 . H641 . 1.09(6) no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C2 . Se1 . C6 . 98.38(13) yes C56 . Se51 . C52 . 98.26(13) yes Se1 . C2 . C3 . 123.2(2) yes Se1 . C2 . C7 . 114.3(2) yes C3 . C2 . C7 . 122.5(3) yes C2 . C3 . C4 . 129.9(3) yes C2 . C3 . H31 . 114.6(18) no C4 . C3 . H31 . 115.3(18) no C3 . C4 . C5 . 113.9(3) yes C3 . C4 . C19 . 106.9(3) yes C5 . C4 . C19 . 111.2(3) yes C3 . C4 . C13 . 108.3(3) yes C5 . C4 . C13 . 106.0(2) yes C19 . C4 . C13 . 110.6(3) yes C4 . C5 . C6 . 129.6(3) yes C4 . C5 . H51 . 121.7(34) no C6 . C5 . H51 . 107.8(33) no Se1 . C6 . C5 . 124.0(2) yes Se1 . C6 . C25 . 112.6(2) yes C5 . C6 . C25 . 123.4(3) yes Se51 . C56 . C55 . 123.8(2) yes Se51 . C56 . C75 . 112.7(2) yes C55 . C56 . C75 . 123.4(3) yes C56 . C55 . C54 . 130.2(3) yes C56 . C55 . H551 . 123.8(29) no C54 . C55 . H551 . 104.9(28) no C55 . C54 . C53 . 113.1(3) yes C55 . C54 . C69 . 107.3(3) yes C53 . C54 . C69 . 111.3(3) yes C55 . C54 . C63 . 108.1(3) yes C53 . C54 . C63 . 105.3(3) yes C69 . C54 . C63 . 111.8(3) yes C54 . C53 . C52 . 130.5(3) yes C54 . C53 . H531 . 110.7(38) no C52 . C53 . H531 . 117.5(39) no Se51 . C52 . C53 . 123.0(2) yes Se51 . C52 . C57 . 112.6(2) yes C53 . C52 . C57 . 124.4(3) yes C2 . C7 . C8 . 121.9(3) yes C2 . C7 . C12 . 119.9(3) yes C8 . C7 . C12 . 118.2(3) yes C7 . C8 . C9 . 119.9(4) yes C7 . C8 . H81 . 120.9(23) no C9 . C8 . H81 . 119.1(23) no C8 . C9 . C10 . 121.3(4) yes C8 . C9 . H91 . 112.8(31) no C10 . C9 . H91 . 124.6(31) no C9 . C10 . C11 . 119.2(4) yes C9 . C10 . H101 . 123.9(32) no C11 . C10 . H101 . 114.9(32) no C10 . C11 . C12 . 121.0(4) yes C10 . C11 . H111 . 123.6(37) no C12 . C11 . H111 . 115.5(38) no C7 . C12 . C11 . 120.4(4) yes C7 . C12 . H121 . 120.7(29) no C11 . C12 . H121 . 118.9(29) no C6 . C25 . C26 . 119.6(3) yes C6 . C25 . C30 . 121.0(3) yes C26 . C25 . C30 . 119.4(3) yes C25 . C26 . C27 . 120.1(3) yes C25 . C26 . H261 . 116.4(19) no C27 . C26 . H261 . 123.1(19) no C26 . C27 . C28 . 120.0(3) yes C26 . C27 . H271 . 112.7(31) no C28 . C27 . H271 . 127.2(31) no C27 . C28 . C29 . 120.5(4) yes C27 . C28 . H281 . 130.1(40) no C29 . C28 . H281 . 107.7(40) no C28 . C29 . C30 . 119.8(3) yes C28 . C29 . H291 . 126.6(30) no C30 . C29 . H291 . 111.8(30) no C25 . C30 . C29 . 120.1(3) yes C25 . C30 . H301 . 124.6(26) no C29 . C30 . H301 . 115.3(26) no C56 . C75 . C80 . 123.3(3) yes C56 . C75 . C76 . 118.8(3) yes C80 . C75 . C76 . 117.9(3) yes C75 . C80 . C79 . 120.9(4) yes C75 . C80 . H801 . 121.8(28) no C79 . C80 . H801 . 117.0(29) no C80 . C79 . C78 . 120.6(4) yes C80 . C79 . H791 . 111.9(26) no C78 . C79 . H791 . 127.4(26) no C79 . C78 . C77 . 120.0(4) yes C79 . C78 . H781 . 115.3(29) no C77 . C78 . H781 . 124.8(29) no C78 . C77 . C76 . 119.3(5) yes C78 . C77 . H771 . 115.9(46) no C76 . C77 . H771 . 124.6(45) no C75 . C76 . C77 . 121.2(4) yes C75 . C76 . H761 . 120.9(31) no C77 . C76 . H761 . 117.8(31) no C52 . C57 . C62 . 121.0(3) yes C52 . C57 . C58 . 121.4(3) yes C62 . C57 . C58 . 117.6(3) yes C57 . C62 . C61 . 120.8(3) yes C57 . C62 . H621 . 113.2(18) no C61 . C62 . H621 . 123.7(18) no C62 . C61 . C60 . 120.5(4) yes C62 . C61 . H611 . 120.2(30) no C60 . C61 . H611 . 118.4(31) no C61 . C60 . C59 . 119.4(3) yes C61 . C60 . H601 . 119.3(34) no C59 . C60 . H601 . 121.3(34) no C60 . C59 . C58 . 120.6(3) yes C60 . C59 . H591 . 114.4(28) no C58 . C59 . H591 . 125.1(28) no C57 . C58 . C59 . 121.0(4) yes C57 . C58 . H581 . 115.0(51) no C59 . C58 . H581 . 120.9(51) no C4 . C19 . C20 . 120.5(3) yes C4 . C19 . C24 . 122.1(3) yes C20 . C19 . C24 . 117.3(3) yes C19 . C20 . C21 . 120.4(4) yes C19 . C20 . H201 . 118.7(26) no C21 . C20 . H201 . 120.6(26) no C20 . C21 . C22 . 121.1(4) yes C20 . C21 . H211 . 113.7(28) no C22 . C21 . H211 . 124.4(28) no C21 . C22 . C23 . 119.3(4) yes C21 . C22 . H221 . 125.9(34) no C23 . C22 . H221 . 114.7(34) no C22 . C23 . C24 . 120.6(4) yes C22 . C23 . H231 . 125.7(32) no C24 . C23 . H231 . 113.3(32) no C19 . C24 . C23 . 121.2(4) yes C19 . C24 . H241 . 115.9(26) no C23 . C24 . H241 . 122.8(26) no C4 . C13 . C18 . 118.4(3) yes C4 . C13 . C14 . 123.4(3) yes C18 . C13 . C14 . 118.0(3) yes C13 . C18 . C17 . 120.3(5) yes C13 . C18 . H181 . 123.3(29) no C17 . C18 . H181 . 116.2(29) no C18 . C17 . C16 . 120.6(5) yes C18 . C17 . H171 . 107.8(39) no C16 . C17 . H171 . 131.3(39) no C17 . C16 . C15 . 119.7(4) yes C17 . C16 . H161 . 133.1(31) no C15 . C16 . H161 . 107.1(31) no C16 . C15 . C14 . 120.3(4) yes C16 . C15 . H151 . 120.3(39) no C14 . C15 . H151 . 119.3(39) no C13 . C14 . C15 . 121.1(4) yes C13 . C14 . H141 . 113.6(31) no C15 . C14 . H141 . 125.2(32) no C54 . C69 . C74 . 119.3(3) yes C54 . C69 . C70 . 122.4(3) yes C74 . C69 . C70 . 118.3(3) yes C69 . C74 . C73 . 120.9(4) yes C69 . C74 . H741 . 119.3(29) no C73 . C74 . H741 . 119.8(30) no C74 . C73 . C72 . 120.2(4) yes C74 . C73 . H731 . 119.9(33) no C72 . C73 . H731 . 117.4(34) no C73 . C72 . C71 . 119.4(4) yes C73 . C72 . H721 . 109.1(33) no C71 . C72 . H721 . 131.5(33) no C72 . C71 . C70 . 120.1(4) yes C72 . C71 . H711 . 111.7(30) no C70 . C71 . H711 . 128.2(30) no C69 . C70 . C71 . 121.1(4) yes C69 . C70 . H701 . 122.6(28) no C71 . C70 . H701 . 116.2(28) no C54 . C63 . C68 . 119.5(3) yes C54 . C63 . C64 . 122.2(3) yes C68 . C63 . C64 . 118.2(4) yes C63 . C68 . C67 . 121.5(5) yes C63 . C68 . H681 . 116.3(24) no C67 . C68 . H681 . 122.1(24) no C68 . C67 . C66 . 120.5(4) yes C68 . C67 . H671 . 122.9(26) no C66 . C67 . H671 . 116.5(26) no C67 . C66 . C65 . 119.5(4) yes C67 . C66 . H661 . 120.5(41) no C65 . C66 . H661 . 119.9(41) no C66 . C65 . C64 . 119.9(5) yes C66 . C65 . H651 . 135.4(61) no C64 . C65 . H651 . 103.6(63) no C63 . C64 . C65 . 120.3(4) yes C63 . C64 . H641 . 116.9(33) no C65 . C64 . H641 . 122.8(33) no data_CRYSTALS_cif3 _database_code_CSD 185126 _audit_creation_date 02-28-04 _audit_creation_method CRYSTALS_ver_28-04-02 _diffrn_measurement_device_type ' Enraf-nonius CAD4 ' _diffrn_radiation_monochromator graphite _computing_data_collection 'CAD-4 software (Enraf-Nonius, 1989)' _computing_data_reduction ; RC93 (Watkin, D.J., Prout, C.K., Lilley, P.M.deQ. 1994) ; _computing_cell_refinement 'CAD-4 software (Enraf-Nonius, 1989)' # end_choice #========================================================================== # General computing #========================================================================== _computing_structure_refinement ; CRYSTALS Issue 10 (Watkin, Prout, Carruthers & Betteridge, 1996) ; _computing_publication_material ; CRYSTALS Issue 10 (Watkin, Prout, Carruthers & Betteridge, 1996) ; _computing_molecular_graphics ; CAMERON (Watkin, Prout & Pearce, 1996) ; # choose one of the following two lines # _computing_structure_solution 'SHELXS86 (Sheldrick, 1986)' _computing_structure_solution 'SIR92 (Giacovazzo et al, 1992)' #========================================================================== _chemical_name_systematic # IUPAC name, in full ; 2',6'-Diphenylspiro[fluorene-9.4'-selenopyran] ; _chemical_melting_point 173-175 # choose from 'full, fullcycle, atomblock, userblock, diagonal, sparse' _refine_ls_matrix_type full # choose from 'heavy, direct, difmap, geom' _atom_sites_solution_primary direct # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom # choose from 'none, undef, noref, refall, refxyz, refU, constr, mixed' _refine_ls_hydrogen_treatment noref #**************************************************************************** _cell_length_a 10.862(3) _cell_angle_alpha 90 _cell_length_b 14.597(3) _cell_angle_beta 90.83(3) _cell_length_c 27.479(3) _cell_angle_gamma 90 _cell_volume 4356.4 _symmetry_cell_setting 'Monoclinic ' _symmetry_space_group_name_H-M 'P 1 21/c 1 ' loop_ _symmetry_equiv_pos_as_xyz 'x,y,z' '-x,-y,-z' '-x,y+1/2,-z+1/2' 'x,-y+1/2,z+1/2' loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source 'C ' 0.0170 0.0090 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International_Tables_Vol_IV_Table_2.2B' 'H ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7997 0.0030 'International_Tables_Vol_IV_Table_2.2B' 'Se ' -0.8790 1.1390 17.0006 2.4098 5.8196 0.2726 3.9731 15.2372 4.3543 43.8163 2.8409 'International_Tables_Vol_IV_Table_2.2B' _chemical_formula_sum ' C29 H20 Se1 ' _chemical_formula_moiety ' C29 H20 Se1 ' _chemical_compound_source ; ? ; _chemical_formula_weight 447.44 _cell_measurement_reflns_used 20 _cell_measurement_theta_min 35 _cell_measurement_theta_max 40 _cell_measurement_temperature 293 _cell_formula_units_Z 8 _exptl_crystal_description ' needle ' _exptl_crystal_colour ' colourless ' _exptl_crystal_size_min 1.00 _exptl_crystal_size_mid 1.00 _exptl_crystal_size_max 1.00 _exptl_crystal_density_diffrn 1.36 _exptl_crystal_density_meas 'not measured' _exptl_crystal_F_000 1820.66 _exptl_absorpt_coefficient_mu 2.41 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details '\y scan,(North et al, 1968)' _exptl_absorpt_correction_T_min 0.07 _exptl_absorpt_correction_T_max 0.09 # Sheldrick geometric definitions 0.09 0.09 _diffrn_standards_interval_time 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 2 _diffrn_standards_decay_% 2.18 _diffrn_ambient_temperature 293 _diffrn_reflns_number 11658 _reflns_number_total 5475 _diffrn_reflns_av_R_equivalents 0.04 # Number of reflections with Friedels Law is 5475 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 5473 _diffrn_measured_fraction_theta_max 1.000 _reflns_number_gt 4485 _diffrn_reflns_theta_min 0.00 _diffrn_reflns_theta_max 55.00 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _reflns_limit_h_min -11 _reflns_limit_h_max 11 _reflns_limit_k_min 0 _reflns_limit_k_max 15 _reflns_limit_l_min 0 _reflns_limit_l_max 29 _refine_diff_density_min -1.56 _refine_diff_density_max 0.83 _reflns_threshold_expression >1.96\s(I) _refine_ls_number_reflns 4485 _refine_ls_number_parameters 541 _refine_ls_R_factor_gt 0.0828 _refine_ls_wR_factor_ref 0.0790 _refine_ls_goodness_of_fit_ref 1.0800 _refine_ls_shift/su_max 0.000340 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Chebychev polynomial with 5 parameters, Carruthers & Watkin , 1979, 21.7 24.0 21.0 8.40 1.47 ; _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54180 _diffrn_measurement_method \w/2\q # Uequiv = arithmetic mean of Ui # i.e. Ueqiv = (U1+U2+U3)/3 loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type Se1 0.05594(5) 0.55890(4) 0.13005(3) 0.0841 1.0000 Uani Se51 0.60531(6) 0.47526(4) 0.42829(3) 0.0912 1.0000 Uani C2 -0.0874(4) 0.4891(3) 0.11556(17) 0.0567 1.0000 Uani C3 -0.1127(4) 0.4113(3) 0.13733(17) 0.0595 1.0000 Uani C4 -0.0419(4) 0.3611(3) 0.17713(17) 0.0572 1.0000 Uani C5 0.0873(4) 0.3977(3) 0.18619(17) 0.0566 1.0000 Uani C6 0.1401(4) 0.4728(3) 0.17017(16) 0.0476 1.0000 Uani C7 -0.1704(5) 0.5321(3) 0.07795(19) 0.0666 1.0000 Uani C8 -0.2948(6) 0.5173(4) 0.0787(2) 0.0808 1.0000 Uani C9 -0.3708(6) 0.5537(5) 0.0431(3) 0.0981 1.0000 Uani C10 -0.3266(8) 0.6083(5) 0.0084(3) 0.1111 1.0000 Uani C11 -0.206(1) 0.6243(7) 0.0071(4) 0.1563 1.0000 Uani C12 -0.1245(7) 0.5879(5) 0.0421(3) 0.1132 1.0000 Uani C13 -0.0342(5) 0.2596(3) 0.1673(2) 0.0684 1.0000 Uani C14 -0.0928(5) 0.2103(4) 0.2041(2) 0.0782 1.0000 Uani C15 -0.0931(6) 0.1145(5) 0.2027(4) 0.1036 1.0000 Uani C16 -0.0382(8) 0.0708(6) 0.1657(4) 0.1179 1.0000 Uani C17 0.0187(8) 0.1176(5) 0.1292(3) 0.1116 1.0000 Uani C18 0.0218(6) 0.2150(4) 0.1297(2) 0.0846 1.0000 Uani C19 -0.1151(4) 0.3626(4) 0.22409(18) 0.0642 1.0000 Uani C20 -0.1452(4) 0.2745(4) 0.2392(2) 0.0722 1.0000 Uani C21 -0.2133(6) 0.2616(7) 0.2810(3) 0.1046 1.0000 Uani C22 -0.2512(6) 0.3361(9) 0.3067(3) 0.1157 1.0000 Uani C23 -0.2209(6) 0.4260(7) 0.2920(3) 0.1053 1.0000 Uani C24 -0.1546(5) 0.4384(5) 0.2508(2) 0.0821 1.0000 Uani C25 0.2674(4) 0.4984(3) 0.18293(16) 0.0460 1.0000 Uani C26 0.3202(4) 0.4749(3) 0.22736(17) 0.0510 1.0000 Uani C27 0.4411(4) 0.4965(3) 0.2380(2) 0.0651 1.0000 Uani C28 0.5122(5) 0.5437(3) 0.2053(2) 0.0735 1.0000 Uani C29 0.4614(5) 0.5698(3) 0.1619(2) 0.0702 1.0000 Uani C30 0.3406(4) 0.5480(3) 0.15007(19) 0.0610 1.0000 Uani C52 0.4757(4) 0.5228(3) 0.39005(16) 0.0511 1.0000 Uani C53 0.3799(5) 0.4728(3) 0.3775(2) 0.0699 1.0000 Uani C54 0.3463(4) 0.3745(3) 0.38993(18) 0.0608 1.0000 Uani C55 0.4404(4) 0.3255(3) 0.42099(19) 0.0689 1.0000 Uani C56 0.5445(4) 0.3568(3) 0.43962(15) 0.0488 1.0000 Uani C57 0.4936(4) 0.6201(3) 0.37639(16) 0.0526 1.0000 Uani C58 0.4095(5) 0.6665(3) 0.3485(2) 0.0690 1.0000 Uani C59 0.4246(5) 0.7595(4) 0.3371(2) 0.0776 1.0000 Uani C60 0.5221(5) 0.8071(3) 0.3534(2) 0.0746 1.0000 Uani C61 0.6079(7) 0.7631(4) 0.3808(3) 0.1159 1.0000 Uani C62 0.5932(6) 0.6708(4) 0.3927(3) 0.1122 1.0000 Uani C63 0.3189(4) 0.3204(3) 0.34335(18) 0.0559 1.0000 Uani C64 0.1949(4) 0.2949(3) 0.34105(17) 0.0540 1.0000 Uani C65 0.1500(5) 0.2441(3) 0.3019(2) 0.0719 1.0000 Uani C66 0.2279(7) 0.2198(4) 0.2654(2) 0.0827 1.0000 Uani C67 0.3489(7) 0.2435(4) 0.2674(2) 0.0877 1.0000 Uani C68 0.3964(5) 0.2938(4) 0.3062(2) 0.0749 1.0000 Uani C69 0.2201(5) 0.3729(3) 0.41371(18) 0.0610 1.0000 Uani C70 0.1344(4) 0.3278(3) 0.38451(19) 0.0600 1.0000 Uani C71 0.0137(5) 0.3184(4) 0.3989(2) 0.0788 1.0000 Uani C72 -0.0200(7) 0.3530(5) 0.4433(3) 0.1039 1.0000 Uani C73 0.0645(9) 0.3956(5) 0.4729(3) 0.1097 1.0000 Uani C74 0.1866(7) 0.4066(4) 0.4586(2) 0.0901 1.0000 Uani C75 0.6316(4) 0.3014(3) 0.46966(15) 0.0504 1.0000 Uani C76 0.6684(5) 0.2149(3) 0.4542(2) 0.0709 1.0000 Uani C77 0.7509(6) 0.1645(4) 0.4810(2) 0.0837 1.0000 Uani C78 0.7980(5) 0.1986(4) 0.5237(2) 0.0812 1.0000 Uani C79 0.7624(5) 0.2824(4) 0.53965(19) 0.0793 1.0000 Uani C80 0.6798(4) 0.3340(4) 0.51314(17) 0.0632 1.0000 Uani H31 -0.1895 0.3800 0.12571 0.0705 1.0000 Uiso H51 0.1408 0.3579 0.20730 0.0655 1.0000 Uiso H81 -0.3308 0.4806 0.1057 0.1000 1.0000 Uiso H91 -0.4608 0.5392 0.0427 0.1178 1.0000 Uiso H101 -0.3828 0.6378 -0.0162 0.1297 1.0000 Uiso H111 -0.172 0.6622 -0.0200 0.1677 1.0000 Uiso H121 -0.0344 0.6020 0.0411 0.1401 1.0000 Uiso H151 -0.1346 0.0792 0.2289 0.1123 1.0000 Uiso H161 -0.0396 0.0024 0.1649 0.1308 1.0000 Uiso H171 0.0587 0.0825 0.1025 0.1292 1.0000 Uiso H181 0.0637 0.2502 0.1035 0.1034 1.0000 Uiso H211 -0.2345 0.1983 0.2920 0.1157 1.0000 Uiso H221 -0.3017 0.3272 0.3365 0.1282 1.0000 Uiso H231 -0.2475 0.4795 0.3120 0.1176 1.0000 Uiso H241 -0.1355 0.5019 0.2395 0.0999 1.0000 Uiso H261 0.2693 0.4421 0.25190 0.0624 1.0000 Uiso H271 0.4777 0.4780 0.2702 0.0758 1.0000 Uiso H281 0.6000 0.5587 0.2133 0.0793 1.0000 Uiso H291 0.5119 0.6050 0.1382 0.0787 1.0000 Uiso H301 0.3047 0.5677 0.11804 0.0694 1.0000 Uiso H531 0.3193 0.5049 0.3557 0.0791 1.0000 Uiso H551 0.4212 0.2602 0.42868 0.0780 1.0000 Uiso H581 0.3350 0.6330 0.3362 0.0766 1.0000 Uiso H591 0.3615 0.7910 0.3162 0.0863 1.0000 Uiso H601 0.5309 0.8738 0.3460 0.0860 1.0000 Uiso H611 0.6835 0.7967 0.3919 0.1247 1.0000 Uiso H621 0.6559 0.6402 0.4141 0.1211 1.0000 Uiso H651 0.0612 0.2262 0.3002 0.0824 1.0000 Uiso H661 0.1961 0.1838 0.2369 0.0922 1.0000 Uiso H671 0.4039 0.2248 0.2403 0.0950 1.0000 Uiso H681 0.4859 0.3099 0.3073 0.0868 1.0000 Uiso H711 -0.0479 0.2866 0.3774 0.0950 1.0000 Uiso H721 -0.1075 0.3483 0.4539 0.1198 1.0000 Uiso H731 0.0391 0.4182 0.5056 0.1249 1.0000 Uiso H741 0.2483 0.4382 0.4802 0.1016 1.0000 Uiso H761 0.6357 0.1902 0.4226 0.0821 1.0000 Uiso H771 0.7756 0.1022 0.4696 0.0953 1.0000 Uiso H781 0.8597 0.1619 0.5427 0.0976 1.0000 Uiso H791 0.7957 0.3064 0.57130 0.0948 1.0000 Uiso H801 0.6549 0.3960 0.52498 0.0751 1.0000 Uiso 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 0.0798(4) 0.0430(4) 0.1286(6) 0.0310(3) -0.0317(4) -0.0099(3) Se51 0.0763(4) 0.0460(4) 0.1497(7) 0.0243(3) -0.0499(4) -0.0154(3) C2 0.066(3) 0.041(3) 0.064(3) 0.002(2) -0.003(2) 0.004(2) C3 0.061(3) 0.050(3) 0.067(3) 0.012(2) -0.010(2) -0.007(2) C4 0.060(3) 0.043(3) 0.068(3) 0.014(2) -0.014(2) -0.012(2) C5 0.055(3) 0.045(3) 0.070(3) 0.011(2) -0.011(2) -0.008(2) C6 0.054(2) 0.030(2) 0.059(3) 0.0032(18) 0.005(2) 0.0038(18) C7 0.085(4) 0.045(3) 0.070(3) 0.007(2) -0.011(3) 0.010(2) C8 0.079(4) 0.083(4) 0.080(4) 0.009(3) -0.012(3) 0.020(3) C9 0.079(4) 0.111(5) 0.103(5) -0.005(4) -0.021(4) 0.033(4) C10 0.127(6) 0.092(5) 0.113(6) 0.020(4) -0.043(5) 0.020(4) C11 0.152(8) 0.165(9) 0.150(8) 0.105(7) -0.053(6) -0.026(7) C12 0.103(5) 0.116(6) 0.120(5) 0.062(5) -0.028(4) -0.006(4) C13 0.068(3) 0.048(3) 0.088(4) 0.013(3) -0.029(3) -0.013(2) C14 0.063(3) 0.056(3) 0.115(4) 0.031(3) -0.036(3) -0.024(3) C15 0.087(4) 0.066(4) 0.157(7) 0.040(5) -0.039(5) -0.025(3) C16 0.111(6) 0.069(5) 0.171(9) 0.015(6) -0.060(6) -0.018(4) C17 0.120(5) 0.081(5) 0.132(6) -0.024(5) -0.058(5) 0.019(4) C18 0.098(4) 0.062(4) 0.093(4) -0.005(3) -0.033(3) 0.003(3) C19 0.052(3) 0.076(4) 0.065(3) 0.016(3) -0.017(2) -0.016(2) C20 0.051(3) 0.076(4) 0.089(4) 0.032(3) -0.018(3) -0.022(3) C21 0.068(4) 0.132(7) 0.113(6) 0.066(5) -0.016(4) -0.027(4) C22 0.064(4) 0.19(1) 0.094(5) 0.026(6) -0.005(4) -0.015(5) C23 0.072(4) 0.157(8) 0.086(5) -0.010(5) -0.006(4) -0.001(4) C24 0.072(3) 0.089(4) 0.086(4) 0.003(3) -0.001(3) -0.011(3) C25 0.050(2) 0.0250(19) 0.063(3) -0.0028(18) 0.010(2) -0.0018(17) C26 0.057(3) 0.036(2) 0.060(3) -0.0038(19) 0.000(2) -0.0010(18) C27 0.063(3) 0.047(3) 0.085(3) -0.004(2) -0.012(3) -0.005(2) C28 0.059(3) 0.043(3) 0.119(5) -0.010(3) -0.002(3) -0.010(2) C29 0.073(3) 0.045(3) 0.092(4) 0.010(3) 0.016(3) -0.012(2) C30 0.065(3) 0.037(2) 0.081(3) 0.009(2) 0.010(2) -0.004(2) C52 0.054(3) 0.039(2) 0.060(3) -0.0017(19) 0.001(2) -0.0016(19) C53 0.070(3) 0.041(3) 0.098(4) 0.027(2) -0.028(3) -0.014(2) C54 0.056(3) 0.041(2) 0.085(3) 0.011(2) -0.017(2) -0.012(2) C55 0.067(3) 0.046(3) 0.093(4) 0.020(2) -0.025(3) -0.012(2) C56 0.056(2) 0.036(2) 0.054(2) -0.0031(19) 0.000(2) 0.0001(19) C57 0.058(3) 0.036(2) 0.064(3) -0.004(2) -0.001(2) -0.006(2) C58 0.062(3) 0.035(2) 0.110(4) 0.007(2) -0.013(3) -0.006(2) C59 0.068(3) 0.049(3) 0.116(4) 0.017(3) -0.001(3) -0.001(2) C60 0.092(4) 0.038(3) 0.094(4) 0.002(3) 0.007(3) -0.012(3) C61 0.116(5) 0.063(4) 0.166(7) 0.034(4) -0.060(5) -0.046(4) C62 0.103(5) 0.064(4) 0.168(7) 0.038(4) -0.071(5) -0.035(3) C63 0.050(3) 0.041(2) 0.077(3) 0.020(2) -0.004(2) 0.0002(19) C64 0.056(3) 0.038(2) 0.068(3) 0.009(2) -0.010(2) -0.0011(19) C65 0.083(3) 0.052(3) 0.080(4) 0.007(3) -0.021(3) -0.008(3) C66 0.117(5) 0.048(3) 0.083(4) 0.007(3) -0.018(4) 0.008(3) C67 0.133(6) 0.056(3) 0.074(4) 0.017(3) 0.011(4) 0.029(4) C68 0.062(3) 0.065(3) 0.099(4) 0.035(3) 0.011(3) 0.013(3) C69 0.078(3) 0.032(2) 0.072(3) 0.005(2) -0.010(3) -0.002(2) C70 0.050(3) 0.045(3) 0.085(3) 0.012(2) -0.003(3) -0.002(2) C71 0.067(3) 0.062(3) 0.107(5) 0.010(3) 0.006(3) 0.000(3) C72 0.082(4) 0.088(5) 0.142(7) 0.014(5) 0.029(4) 0.010(4) C73 0.148(7) 0.074(4) 0.109(5) -0.000(4) 0.045(5) 0.026(5) C74 0.121(5) 0.056(3) 0.093(5) -0.004(3) -0.011(4) 0.003(3) C75 0.050(2) 0.050(3) 0.051(3) 0.003(2) 0.002(2) -0.0042(19) C76 0.092(4) 0.046(3) 0.074(3) -0.003(2) -0.022(3) 0.011(2) C77 0.111(4) 0.049(3) 0.090(4) 0.003(3) -0.021(3) 0.020(3) C78 0.082(4) 0.079(4) 0.082(4) 0.018(3) -0.008(3) 0.023(3) C79 0.086(4) 0.092(4) 0.059(3) 0.001(3) -0.018(3) 0.004(3) C80 0.068(3) 0.064(3) 0.057(3) -0.003(2) -0.003(2) 0.005(2) _refine_ls_extinction_method 'None' loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Se1 . C2 . 1.898(5) yes Se1 . C6 . 1.898(4) yes Se51 . C52 . 1.878(4) yes Se51 . C56 . 1.878(4) yes C2 . C3 . 1.315(7) yes C2 . C7 . 1.499(7) yes C3 . C4 . 1.516(6) yes C3 . H31 . 1.000 no C4 . C5 . 1.519(6) yes C4 . C13 . 1.508(7) yes C4 . C19 . 1.525(7) yes C5 . C6 . 1.315(6) yes C5 . H51 . 1.000 no C6 . C25 . 1.470(6) yes C7 . C8 . 1.369(8) yes C7 . C12 . 1.378(9) yes C8 . C9 . 1.377(8) yes C8 . H81 . 1.000 no C9 . C10 . 1.34(1) yes C9 . H91 . 1.000 no C10 . C11 . 1.335(12) yes C10 . H101 . 1.000 no C11 . C12 . 1.40(1) yes C11 . H111 . 1.000 no C12 . H121 . 1.000 no C13 . C14 . 1.401(8) yes C13 . C18 . 1.370(8) yes C14 . C15 . 1.399(9) yes C14 . C20 . 1.466(9) yes C15 . C16 . 1.346(12) yes C15 . H151 . 1.000 no C16 . C17 . 1.368(12) yes C16 . H161 . 1.000 no C17 . C18 . 1.42(1) yes C17 . H171 . 1.000 no C18 . H181 . 1.000 no C19 . C20 . 1.393(7) yes C19 . C24 . 1.398(8) yes C20 . C21 . 1.387(9) yes C21 . C22 . 1.364(12) yes C21 . H211 . 1.000 no C22 . C23 . 1.413(12) yes C22 . H221 . 1.000 no C23 . C24 . 1.363(9) yes C23 . H231 . 1.000 no C24 . H241 . 1.000 no C25 . C26 . 1.384(6) yes C25 . C30 . 1.412(6) yes C26 . C27 . 1.378(7) yes C26 . H261 . 1.000 no C27 . C28 . 1.377(8) yes C27 . H271 . 1.000 no C28 . C29 . 1.363(8) yes C28 . H281 . 1.000 no C29 . C30 . 1.383(7) yes C29 . H291 . 1.000 no C30 . H301 . 1.000 no C52 . C53 . 1.314(7) yes C52 . C57 . 1.482(6) yes C53 . C54 . 1.520(6) yes C53 . H531 . 1.000 no C54 . C55 . 1.503(6) yes C54 . C63 . 1.530(7) yes C54 . C69 . 1.527(7) yes C55 . C56 . 1.317(6) yes C55 . H551 . 1.000 no C56 . C75 . 1.486(6) yes C57 . C58 . 1.364(7) yes C57 . C62 . 1.380(7) yes C58 . C59 . 1.403(7) yes C58 . H581 . 1.000 no C59 . C60 . 1.338(8) yes C59 . H591 . 1.000 no C60 . C61 . 1.352(8) yes C60 . H601 . 1.000 no C61 . C62 . 1.396(8) yes C61 . H611 . 1.000 no C62 . H621 . 1.000 no C63 . C64 . 1.399(6) yes C63 . C68 . 1.387(7) yes C64 . C65 . 1.390(7) yes C64 . C70 . 1.453(7) yes C65 . C66 . 1.367(8) yes C65 . H651 . 1.000 no C66 . C67 . 1.359(9) yes C66 . H661 . 1.000 no C67 . C68 . 1.387(9) yes C67 . H671 . 1.000 no C68 . H681 . 1.000 no C69 . C70 . 1.386(7) yes C69 . C74 . 1.382(8) yes C70 . C71 . 1.381(7) yes C71 . C72 . 1.38(1) yes C71 . H711 . 1.000 no C72 . C73 . 1.367(11) yes C72 . H721 . 1.000 no C73 . C74 . 1.398(11) yes C73 . H731 . 1.000 no C74 . H741 . 1.000 no C75 . C76 . 1.392(7) yes C75 . C80 . 1.382(6) yes C76 . C77 . 1.367(7) yes C76 . H761 . 1.000 no C77 . C78 . 1.365(8) yes C77 . H771 . 1.000 no C78 . C79 . 1.359(8) yes C78 . H781 . 1.000 no C79 . C80 . 1.373(7) yes C79 . H791 . 1.000 no C80 . H801 . 1.000 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C2 . Se1 . C6 . 98.80(18) yes C52 . Se51 . C56 . 99.83(18) yes Se1 . C2 . C3 . 123.0(4) yes Se1 . C2 . C7 . 113.8(3) yes C3 . C2 . C7 . 123.2(4) yes C2 . C3 . C4 . 129.7(4) yes C2 . C3 . H31 . 115.4(3) no C4 . C3 . H31 . 114.9(2) no C3 . C4 . C5 . 113.9(4) yes C3 . C4 . C13 . 112.0(4) yes C5 . C4 . C13 . 108.8(4) yes C3 . C4 . C19 . 109.8(4) yes C5 . C4 . C19 . 110.3(4) yes C13 . C4 . C19 . 101.3(4) yes C4 . C5 . C6 . 130.1(4) yes C4 . C5 . H51 . 114.7(2) no C6 . C5 . H51 . 115.2(3) no Se1 . C6 . C5 . 122.5(3) yes Se1 . C6 . C25 . 114.4(3) yes C5 . C6 . C25 . 123.0(4) yes C2 . C7 . C8 . 120.5(5) yes C2 . C7 . C12 . 121.4(5) yes C8 . C7 . C12 . 118.1(5) yes C7 . C8 . C9 . 120.7(6) yes C7 . C8 . H81 . 119.5(3) no C9 . C8 . H81 . 119.8(5) no C8 . C9 . C10 . 121.2(7) yes C8 . C9 . H91 . 120.1(5) no C10 . C9 . H91 . 118.7(4) no C9 . C10 . C11 . 119.1(6) yes C9 . C10 . H101 . 121.0(4) no C11 . C10 . H101 . 119.9(4) no C10 . C11 . C12 . 121.7(8) yes C10 . C11 . H111 . 119.1(5) no C12 . C11 . H111 . 119.2(5) no C7 . C12 . C11 . 119.0(7) yes C7 . C12 . H121 . 120.3(4) no C11 . C12 . H121 . 120.7(5) no C4 . C13 . C14 . 110.4(5) yes C4 . C13 . C18 . 128.9(5) yes C14 . C13 . C18 . 120.7(5) yes C13 . C14 . C15 . 119.6(7) yes C13 . C14 . C20 . 109.3(5) yes C15 . C14 . C20 . 131.0(7) yes C14 . C15 . C16 . 119.6(8) yes C14 . C15 . H151 . 119.7(5) no C16 . C15 . H151 . 120.7(5) no C15 . C16 . C17 . 121.8(8) yes C15 . C16 . H161 . 118.9(5) no C17 . C16 . H161 . 119.4(5) no C16 . C17 . C18 . 120.1(8) yes C16 . C17 . H171 . 119.2(5) no C18 . C17 . H171 . 120.7(5) no C13 . C18 . C17 . 118.2(7) yes C13 . C18 . H181 . 120.7(3) no C17 . C18 . H181 . 121.1(5) no C4 . C19 . C20 . 111.5(5) yes C4 . C19 . C24 . 128.6(5) yes C20 . C19 . C24 . 119.9(5) yes C14 . C20 . C19 . 107.4(5) yes C14 . C20 . C21 . 132.4(6) yes C19 . C20 . C21 . 120.2(7) yes C20 . C21 . C22 . 119.3(7) yes C20 . C21 . H211 . 120.3(5) no C22 . C21 . H211 . 120.4(5) no C21 . C22 . C23 . 121.2(7) yes C21 . C22 . H221 . 119.6(5) no C23 . C22 . H221 . 119.2(5) no C22 . C23 . C24 . 119.3(8) yes C22 . C23 . H231 . 119.8(5) no C24 . C23 . H231 . 120.8(5) no C19 . C24 . C23 . 120.0(7) yes C19 . C24 . H241 . 120.3(3) no C23 . C24 . H241 . 119.6(5) no C6 . C25 . C26 . 121.6(4) yes C6 . C25 . C30 . 121.0(4) yes C26 . C25 . C30 . 117.4(4) yes C25 . C26 . C27 . 120.8(4) yes C25 . C26 . H261 . 119.2(2) no C27 . C26 . H261 . 120.0(3) no C26 . C27 . C28 . 121.1(5) yes C26 . C27 . H271 . 119.4(3) no C28 . C27 . H271 . 119.5(3) no C27 . C28 . C29 . 119.2(5) yes C27 . C28 . H281 . 120.6(3) no C29 . C28 . H281 . 120.2(3) no C28 . C29 . C30 . 120.8(5) yes C28 . C29 . H291 . 119.7(3) no C30 . C29 . H291 . 119.5(3) no C25 . C30 . C29 . 120.6(5) yes C25 . C30 . H301 . 119.6(3) no C29 . C30 . H301 . 119.8(3) no Se51 . C52 . C53 . 121.7(3) yes Se51 . C52 . C57 . 113.3(3) yes C53 . C52 . C57 . 124.9(4) yes C52 . C53 . C54 . 131.1(4) yes C52 . C53 . H531 . 114.1(3) no C54 . C53 . H531 . 114.8(2) no C53 . C54 . C55 . 114.4(4) yes C53 . C54 . C63 . 110.1(4) yes C55 . C54 . C63 . 110.6(4) yes C53 . C54 . C69 . 109.3(4) yes C55 . C54 . C69 . 110.9(4) yes C63 . C54 . C69 . 100.7(3) yes C54 . C55 . C56 . 129.0(4) yes C54 . C55 . H551 . 115.5(2) no C56 . C55 . H551 . 115.4(3) no Se51 . C56 . C55 . 123.8(3) yes Se51 . C56 . C75 . 111.8(3) yes C55 . C56 . C75 . 124.3(4) yes C52 . C57 . C58 . 121.9(4) yes C52 . C57 . C62 . 122.5(4) yes C58 . C57 . C62 . 115.5(4) yes C57 . C58 . C59 . 121.8(5) yes C57 . C58 . H581 . 118.6(3) no C59 . C58 . H581 . 119.6(3) no C58 . C59 . C60 . 121.4(5) yes C58 . C59 . H591 . 119.4(3) no C60 . C59 . H591 . 119.1(3) no C59 . C60 . C61 . 118.4(5) yes C59 . C60 . H601 . 121.0(3) no C61 . C60 . H601 . 120.6(3) no C60 . C61 . C62 . 120.6(5) yes C60 . C61 . H611 . 119.5(3) no C62 . C61 . H611 . 119.9(4) no C57 . C62 . C61 . 122.3(6) yes C57 . C62 . H621 . 118.5(3) no C61 . C62 . H621 . 119.3(4) no C54 . C63 . C64 . 110.5(4) yes C54 . C63 . C68 . 130.3(4) yes C64 . C63 . C68 . 119.1(5) yes C63 . C64 . C65 . 120.3(5) yes C63 . C64 . C70 . 108.7(4) yes C65 . C64 . C70 . 131.0(5) yes C64 . C65 . C66 . 119.5(5) yes C64 . C65 . H651 . 120.2(3) no C66 . C65 . H651 . 120.3(4) no C65 . C66 . C67 . 120.8(6) yes C65 . C66 . H661 . 120.0(4) no C67 . C66 . H661 . 119.2(4) no C66 . C67 . C68 . 121.0(6) yes C66 . C67 . H671 . 119.2(4) no C68 . C67 . H671 . 119.8(4) no C63 . C68 . C67 . 119.3(5) yes C63 . C68 . H681 . 120.8(3) no C67 . C68 . H681 . 119.9(4) no C54 . C69 . C70 . 111.0(4) yes C54 . C69 . C74 . 128.8(5) yes C70 . C69 . C74 . 120.2(5) yes C64 . C70 . C69 . 109.0(4) yes C64 . C70 . C71 . 130.1(5) yes C69 . C70 . C71 . 120.9(5) yes C70 . C71 . C72 . 118.9(6) yes C70 . C71 . H711 . 120.5(4) no C72 . C71 . H711 . 120.6(4) no C71 . C72 . C73 . 120.7(6) yes C71 . C72 . H721 . 120.0(4) no C73 . C72 . H721 . 119.3(5) no C72 . C73 . C74 . 121.1(7) yes C72 . C73 . H731 . 119.6(5) no C74 . C73 . H731 . 119.3(5) no C69 . C74 . C73 . 118.2(6) yes C69 . C74 . H741 . 120.7(4) no C73 . C74 . H741 . 121.1(5) no C56 . C75 . C76 . 120.5(4) yes C56 . C75 . C80 . 121.5(4) yes C76 . C75 . C80 . 118.1(4) yes C75 . C76 . C77 . 120.8(5) yes C75 . C76 . H761 . 119.5(3) no C77 . C76 . H761 . 119.7(3) no C76 . C77 . C78 . 120.1(5) yes C76 . C77 . H771 . 119.8(3) no C78 . C77 . H771 . 120.1(3) no C77 . C78 . C79 . 120.0(5) yes C77 . C78 . H781 . 119.6(3) no C79 . C78 . H781 . 120.3(3) no C78 . C79 . C80 . 120.6(5) yes C78 . C79 . H791 . 119.7(3) no C80 . C79 . H791 . 119.7(3) no C75 . C80 . C79 . 120.4(5) yes C75 . C80 . H801 . 119.5(3) no C79 . C80 . H801 . 120.1(3) no