# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Jeremy Rawson' _publ_contact_author_address ; Dept. of Chemistry University of Cambridge Lensfield Road Cambridge CB2 1EW UNITED KINGDOM ; _publ_contact_author_email JMR31@CAM.AC.UK _publ_section_title ; Crystal structures and magnetic properties of a sterically encumbered dithiadiazolyl radical, 2,4,6-(F3C)3C6H2CNSSN ; _publ_contact_author_fax '(01223) 336362' _publ_contact_author_phone '(01223) 336317' loop_ _publ_author_name 'J. Rawson' 'Antonio Alberola' 'Caroline S. Clarke' 'Delia A. Haynes' 'Sofia I. Pascu' #===END data_jr0336 _database_code_depnum_ccdc_archive 'CCDC 274725' _audit_creation_date 05-06-08 _audit_creation_method CRYSTALS_ver_12.20 ###################################### ## denoted 1b in text ## ###################################### #========================================================================== _chemical_name_systematic # IUPAC name, in full ; ? ; _chemical_melting_point ? _refine_ls_matrix_type full _atom_sites_solution_primary direct _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment noref #**************************************************************************** # General computing #============================================================= _computing_structure_refinement ; CRYSTALS (Watkin et al 2003) ; _computing_publication_material ; CRYSTALS (Watkin et al 2003) ; _computing_molecular_graphics ; CAMERON (Watkin et al 1996) ; #============================================================= _cell_length_a 8.2750(2) _cell_angle_alpha 101.1251(8) _cell_length_b 16.5911(4) _cell_angle_beta 94.1342(8) _cell_length_c 20.2044(6) _cell_angle_gamma 101.1281(15) _cell_volume 2653.31(12) _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1 ' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z # choose from: rm (reference molecule of # known chirality), ad (anomolous # dispersion - ie. Flack param), rmad # (both rm and ad), syn (known from # synthetic pathway), unk (unknown) # or . (not applicable). _chemical_absolute_configuration . 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 ' 0.0033 0.0016 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 57.7998 0.0030 International_Tables_Vol_IV_Table_2.2B 'F ' 0.0171 0.0103 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476 0.2776 International_Tables_Vol_IV_Table_2.2B 'N ' 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 International_Tables_Vol_IV_Table_2.2B 'S ' 0.1246 0.1234 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720 0.8669 International_Tables_Vol_IV_Table_2.2B _cell_formula_units_Z 2 _chemical_formula_sum ' C40 H8 F36 N8 S8 ' _chemical_formula_moiety ' 4 (C10 H2 F9 N2 S2 ' _chemical_compound_source ; ? ; _chemical_formula_weight 1541.12 _cell_measurement_reflns_used 25518 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27 _cell_measurement_temperature 180 _exptl_crystal_description ' block ' _exptl_crystal_colour ' yellow ' _exptl_crystal_size_min 0.10 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_max 0.30 _exptl_crystal_density_diffrn 1.929 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 1512 _exptl_absorpt_coefficient_mu 0.507 _diffrn_measurement_device_type ; Nonius Kappa CCD ; _diffrn_radiation_monochromator graphite _computing_data_collection ; COLLECT (Nonius BV, 1997) ; _computing_data_reduction ; Denzo/Scalepack (Otwinowski & Minor, 1996) ; _computing_cell_refinement ; Denzo/Scalepack (Otwinowski & Minor, 1996) ; _computing_structure_solution ; SIR92 (Altomare et al, 1994) ; _diffrn_measurement_method \w _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.827 _exptl_absorpt_correction_T_max 0.988 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _diffrn_standards_interval_time 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0.00 _diffrn_ambient_temperature 180 _diffrn_reflns_number 25701 _reflns_number_total 11625 _diffrn_reflns_av_R_equivalents 0.05 # Number of reflections with Friedels Law is 11625 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 11790 _diffrn_reflns_theta_min 2.068 _diffrn_reflns_theta_max 27.170 _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 25.539 _diffrn_measured_fraction_theta_full 0.995 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 25 _reflns_limit_h_min -10 _reflns_limit_h_max 10 _reflns_limit_k_min -21 _reflns_limit_k_max 20 _reflns_limit_l_min 0 _reflns_limit_l_max 25 _refine_diff_density_min -0.46 _refine_diff_density_max 0.93 _refine_ls_number_reflns 5223 _refine_ls_number_restraints 48 _refine_ls_number_parameters 856 #_refine_ls_R_factor_ref 0.0527 _refine_ls_wR_factor_ref 0.0573 _refine_ls_goodness_of_fit_ref 1.2003 #_reflns_number_all 11582 _refine_ls_R_factor_all 0.1329 _refine_ls_wR_factor_all 0.0806 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>3.00u(I) _reflns_number_gt 5223 _refine_ls_R_factor_gt 0.0527 _refine_ls_wR_factor_gt 0.0573 _refine_ls_shift/su_max 0.038252 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 1.84 1.52 1.44 ; _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _exptl_special_details ; One CF3 unit disordered over two positions was modelled with 0.5 occupancies: Small weakly diffracting crystal of irregual shape accounts for shortage of data ; ## -------------------REFERENCES ----------------------## ## Insert your own references - in alphabetic order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo G., Guagliardi A., Burla M.C., Polidori, G. & Camalli, M. (1994) SIR92 - a program for automatic solution of crystal structures by direct methods. J. Appl. Cryst. (27), 435-435 Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K., Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Nonius BV, COLLECT Software, 1997-2001) Otwinowski, Z. & Minor, W. (1996), Processing of X-ray Diffraction Data Collected in Oscillation Mode. Methods Enzymol. 276, 1997, 307-326. Ed Carter, C.W. & Sweet, R.M., Academic Press. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Watkin D.J. (1994), Acta Cryst, A50, 411-437 Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996) CAMERON, Chemical Crystallography Laboratory, OXFORD, UK. ; # Uequiv = arithmetic mean of Ui # i.e. Ueqiv = (U1+U2+U3)/3 # Replace trailing . with the number of unfound # hydrogen atoms attaced to relavent atom 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens S1 S 1.0507(2) 0.07390(9) 0.30504(7) 0.0477 1.0000 Uani . . . . . . S2 S 1.19588(18) 0.19136(9) 0.30573(7) 0.0446 1.0000 Uani . . . . . . S3 S 1.2131(2) 0.07830(12) 0.49729(9) 0.0574 1.0000 Uani . . . . . . S4 S 1.0760(2) 0.10024(12) 0.57928(8) 0.0590 1.0000 Uani . . . . . . S5 S 0.69484(18) 0.62710(9) 0.78318(8) 0.0466 1.0000 Uani . . . . . . S6 S 0.92488(18) 0.62724(9) 0.74761(8) 0.0456 1.0000 Uani . . . . . . S7 S 1.01125(17) 0.10582(8) 0.82992(8) 0.0416 1.0000 Uani . . . . . . S8 S 1.25004(17) 0.11233(8) 0.80145(7) 0.0394 1.0000 Uani . . . . . . N1 N 0.9505(5) 0.0646(3) 0.2302(2) 0.0354 1.0000 Uani . . . . . . N2 N 1.1114(5) 0.1974(2) 0.2313(2) 0.0342 1.0000 Uani . . . . . . N3 N 1.1413(5) 0.1428(3) 0.4574(2) 0.0411 1.0000 Uani . . . . . . N4 N 0.9863(6) 0.1676(3) 0.5498(2) 0.0407 1.0000 Uani . . . . . . N5 N 0.6412(5) 0.5246(3) 0.7705(2) 0.0382 1.0000 Uani . . . . . . N6 N 0.9022(6) 0.5253(3) 0.7326(3) 0.0428 1.0000 Uani . . . . . . N7 N 1.0300(5) 0.2078(3) 0.8498(2) 0.0401 1.0000 Uani . . . . . . N8 N 1.2976(5) 0.2151(3) 0.8181(2) 0.0372 1.0000 Uani . . . . . . F1 F 1.2482(4) 0.1909(2) 0.09266(17) 0.0480 1.0000 Uani . . . . . . F2 F 1.1868(4) 0.0654(2) 0.11071(17) 0.0492 1.0000 Uani . . . . . . F3 F 1.1693(4) 0.0858(2) 0.00924(16) 0.0555 1.0000 Uani . . . . . . F4 F 0.6872(10) 0.1639(7) -0.0890(4) 0.0657 0.5000 Uani D U . . . . F5 F 0.5374(12) 0.0471(6) -0.0763(5) 0.0703 0.5000 Uani D U . . . . F6 F 0.4754(10) 0.1620(6) -0.0381(4) 0.0545 0.5000 Uani D U . . . . F40 F 0.6728(10) 0.1068(7) -0.1032(4) 0.0602 0.5000 Uani D U . . . . F50 F 0.5395(13) 0.1905(6) -0.0505(5) 0.0677 0.5000 Uani D U . . . . F60 F 0.4671(10) 0.0617(7) -0.0573(4) 0.0630 0.5000 Uani D U . . . . F7 F 0.5184(4) 0.1872(2) 0.19575(17) 0.0591 1.0000 Uani . . . . . . F8 F 0.7473(4) 0.1968(2) 0.25546(15) 0.0503 1.0000 Uani . . . . . . F9 F 0.5871(5) 0.0762(2) 0.21669(18) 0.0621 1.0000 Uani . . . . . . F10 F 0.6269(5) 0.1236(2) 0.49040(18) 0.0592 1.0000 Uani . . . . . . F11 F 0.7625(4) 0.06603(19) 0.41508(19) 0.0548 1.0000 Uani . . . . . . F12 F 0.5456(4) 0.1088(2) 0.3852(2) 0.0621 1.0000 Uani . . . . . . F13 F 0.7012(7) 0.3833(3) 0.2994(2) 0.0888 1.0000 Uani . . . . . . F14 F 0.5701(6) 0.4077(4) 0.3864(3) 0.1124 1.0000 Uani . . . . . . F15 F 0.8010(7) 0.4833(3) 0.3811(3) 0.0999 1.0000 Uani . . . . . . F16 F 1.3205(4) 0.3100(3) 0.44823(18) 0.0701 1.0000 Uani . . . . . . F17 F 1.2695(6) 0.4305(2) 0.4892(2) 0.0814 1.0000 Uani . . . . . . F18 F 1.2423(5) 0.3348(2) 0.54732(16) 0.0613 1.0000 Uani . . . . . . F19 F 0.6295(5) 0.4520(2) 0.61244(18) 0.0610 1.0000 Uani . . . . . . F20 F 0.6223(5) 0.3331(2) 0.54836(16) 0.0596 1.0000 Uani . . . . . . F21 F 0.8555(5) 0.4136(2) 0.59054(18) 0.0606 1.0000 Uani . . . . . . F22 F 0.7558(7) 0.0938(2) 0.6624(3) 0.0947 1.0000 Uani . . . . . . F23 F 0.4974(7) 0.0896(3) 0.6455(3) 0.1150 1.0000 Uani . . . . . . F24 F 0.6080(5) 0.0885(2) 0.7419(2) 0.0660 1.0000 Uani . . . . . . F25 F 0.6015(4) 0.4174(2) 0.87749(17) 0.0532 1.0000 Uani . . . . . . F26 F 0.8590(4) 0.4620(2) 0.87131(16) 0.0529 1.0000 Uani . . . . . . F27 F 0.7795(6) 0.3457(2) 0.89938(17) 0.0671 1.0000 Uani . . . . . . F28 F 1.3249(4) 0.3187(2) 0.71020(16) 0.0539 1.0000 Uani . . . . . . F29 F 1.0699(4) 0.2727(2) 0.71648(16) 0.0513 1.0000 Uani . . . . . . F30 F 1.1456(5) 0.3898(2) 0.68819(17) 0.0649 1.0000 Uani . . . . . . F31 F 1.3601(9) 0.6476(2) 0.8554(3) 0.1302 1.0000 Uani . . . . . . F32 F 1.1398(6) 0.6378(2) 0.8975(3) 0.0977 1.0000 Uani . . . . . . F33 F 1.3548(8) 0.6489(3) 0.9592(3) 0.1165 1.0000 Uani . . . . . . F34 F 1.0615(6) 0.3183(3) 0.9924(2) 0.0785 1.0000 Uani . . . . . . F35 F 1.2895(6) 0.4002(2) 1.03937(17) 0.0776 1.0000 Uani . . . . . . F36 F 1.2916(5) 0.2827(2) 0.97395(17) 0.0626 1.0000 Uani . . . . . . C1 C 0.9930(6) 0.1317(3) 0.2029(2) 0.0291 1.0000 Uani . . . . . . C2 C 0.8961(6) 0.1329(3) 0.1377(2) 0.0261 1.0000 Uani . . . . . . C3 C 0.7304(6) 0.1412(3) 0.1376(2) 0.0300 1.0000 Uani . . . . . . C4 C 0.6372(6) 0.1405(3) 0.0771(2) 0.0337 1.0000 Uani . . . . . . C5 C 0.7061(6) 0.1309(3) 0.0167(2) 0.0293 1.0000 Uani . . . . . . C6 C 0.8708(6) 0.1249(3) 0.0166(2) 0.0304 1.0000 Uani . . . . . . C7 C 0.9648(6) 0.1252(3) 0.0765(2) 0.0278 1.0000 Uani . . . . . . C8 C 1.1405(7) 0.1170(4) 0.0726(2) 0.0361 1.0000 Uani . . . . . . C9 C 0.6031(7) 0.1256(4) -0.0480(3) 0.0501 1.0000 Uani D U . . . . C10 C 0.6465(7) 0.1505(4) 0.2013(3) 0.0390 1.0000 Uani . . . . . . C11 C 1.0302(6) 0.1801(3) 0.4904(2) 0.0351 1.0000 Uani . . . . . . C12 C 0.9517(7) 0.2385(3) 0.4579(2) 0.0346 1.0000 Uani . . . . . . C13 C 0.7844(6) 0.2132(3) 0.4300(2) 0.0322 1.0000 Uani . . . . . . C14 C 0.7082(7) 0.2677(3) 0.4007(3) 0.0378 1.0000 Uani . . . . . . C15 C 0.7983(7) 0.3470(3) 0.3992(3) 0.0412 1.0000 Uani . . . . . . C16 C 0.9628(8) 0.3717(4) 0.4266(3) 0.0467 1.0000 Uani . . . . . . C17 C 1.0387(7) 0.3175(3) 0.4549(2) 0.0386 1.0000 Uani . . . . . . C18 C 0.6817(7) 0.1285(3) 0.4298(3) 0.0381 1.0000 Uani . . . . . . C19 C 0.7117(9) 0.4031(4) 0.3665(4) 0.0596 1.0000 Uani . . . . . . C20 C 1.2170(8) 0.3487(4) 0.4857(3) 0.0523 1.0000 Uani . . . . . . C21 C 0.7570(6) 0.4859(3) 0.7458(2) 0.0317 1.0000 Uani . . . . . . C22 C 0.7224(6) 0.3919(3) 0.7318(3) 0.0327 1.0000 Uani . . . . . . C23 C 0.6984(6) 0.3454(3) 0.6649(2) 0.0311 1.0000 Uani . . . . . . C24 C 0.6700(6) 0.2583(3) 0.6516(3) 0.0344 1.0000 Uani . . . . . . C25 C 0.6623(6) 0.2162(3) 0.7045(3) 0.0328 1.0000 Uani . . . . . . C26 C 0.6858(6) 0.2605(3) 0.7709(3) 0.0340 1.0000 Uani . . . . . . C27 C 0.7161(6) 0.3478(3) 0.7851(2) 0.0302 1.0000 Uani . . . . . . C28 C 0.7394(7) 0.3940(3) 0.8579(3) 0.0382 1.0000 Uani . . . . . . C29 C 0.6295(8) 0.1226(4) 0.6884(3) 0.0470 1.0000 Uani . . . . . . C30 C 0.7022(7) 0.3867(4) 0.6044(3) 0.0421 1.0000 Uani . . . . . . C32 C 1.1744(6) 0.2501(3) 0.8405(2) 0.0305 1.0000 Uani . . . . . . C33 C 1.2035(6) 0.3444(3) 0.8557(2) 0.0306 1.0000 Uani . . . . . . C34 C 1.2108(6) 0.3881(3) 0.8032(2) 0.0323 1.0000 Uani . . . . . . C35 C 1.2379(6) 0.4750(3) 0.8167(3) 0.0346 1.0000 Uani . . . . . . C36 C 1.2582(6) 0.5192(3) 0.8836(3) 0.0356 1.0000 Uani . . . . . . C37 C 1.2498(6) 0.4768(3) 0.9361(3) 0.0385 1.0000 Uani . . . . . . C38 C 1.2237(6) 0.3899(3) 0.9224(3) 0.0345 1.0000 Uani . . . . . . C39 C 1.2156(9) 0.3475(4) 0.9816(3) 0.0507 1.0000 Uani . . . . . . C40 C 1.2810(7) 0.6118(4) 0.8984(3) 0.0472 1.0000 Uani . . . . . . C41 C 1.1900(7) 0.3433(3) 0.7289(3) 0.0379 1.0000 Uani . . . . . . H41 H 0.5190 0.1484 0.0780 0.0385 1.0000 Uiso . . . . . . H61 H 0.9230 0.1192 -0.0276 0.0360 1.0000 Uiso . . . . . . H141 H 0.5872 0.2500 0.3808 0.0522 1.0000 Uiso . . . . . . H161 H 1.0278 0.4298 0.4252 0.0556 1.0000 Uiso . . . . . . H241 H 0.6536 0.2254 0.6027 0.0406 1.0000 Uiso . . . . . . H261 H 0.6815 0.2297 0.8098 0.0403 1.0000 Uiso . . . . . . H351 H 1.2444 0.5065 0.7784 0.0404 1.0000 Uiso . . . . . . H371 H 1.2650 0.5096 0.9847 0.0458 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 S1 0.0677(10) 0.0417(8) 0.0330(7) 0.0129(6) -0.0052(7) 0.0087(7) S2 0.0466(8) 0.0446(8) 0.0369(8) 0.0058(6) -0.0090(6) 0.0036(6) S3 0.0474(9) 0.0840(12) 0.0586(10) 0.0366(9) 0.0181(7) 0.0313(8) S4 0.0668(11) 0.0811(13) 0.0477(9) 0.0368(9) 0.0195(8) 0.0325(9) S5 0.0429(8) 0.0332(8) 0.0635(10) 0.0035(7) 0.0163(7) 0.0108(6) S6 0.0394(8) 0.0318(8) 0.0640(10) 0.0072(7) 0.0137(7) 0.0042(6) S7 0.0412(8) 0.0306(7) 0.0522(8) 0.0069(6) 0.0154(6) 0.0039(6) S8 0.0381(7) 0.0326(7) 0.0492(8) 0.0062(6) 0.0092(6) 0.0121(6) N1 0.048(3) 0.029(2) 0.031(2) 0.0091(18) 0.0038(19) 0.0091(19) N2 0.038(2) 0.027(2) 0.034(2) 0.0037(18) -0.0009(18) 0.0027(18) N3 0.035(2) 0.053(3) 0.039(3) 0.012(2) 0.010(2) 0.012(2) N4 0.045(3) 0.045(3) 0.037(3) 0.014(2) 0.009(2) 0.014(2) N5 0.036(2) 0.029(2) 0.048(3) 0.004(2) 0.013(2) 0.0048(19) N6 0.038(3) 0.026(2) 0.064(3) 0.006(2) 0.012(2) 0.0076(19) N7 0.038(3) 0.031(2) 0.052(3) 0.008(2) 0.017(2) 0.0054(19) N8 0.033(2) 0.032(2) 0.046(3) 0.004(2) 0.0095(19) 0.0097(19) F1 0.0284(16) 0.054(2) 0.061(2) 0.0133(16) 0.0063(14) 0.0061(14) F2 0.0381(17) 0.060(2) 0.060(2) 0.0206(17) 0.0094(15) 0.0252(15) F3 0.0409(19) 0.087(3) 0.0410(19) 0.0023(17) 0.0142(15) 0.0269(17) F4 0.057(4) 0.101(4) 0.042(3) 0.040(3) -0.006(3) 0.001(4) F5 0.072(4) 0.075(4) 0.055(4) 0.001(3) -0.024(4) 0.019(4) F6 0.040(3) 0.093(5) 0.040(3) 0.020(3) 0.005(3) 0.030(3) F40 0.045(3) 0.104(4) 0.033(3) 0.004(3) 0.004(2) 0.030(4) F50 0.074(5) 0.075(4) 0.056(4) 0.012(3) -0.017(4) 0.033(3) F60 0.047(4) 0.095(4) 0.040(3) 0.020(3) -0.003(3) -0.005(3) F7 0.046(2) 0.096(3) 0.0440(19) 0.0136(19) 0.0142(15) 0.0338(19) F8 0.0473(19) 0.066(2) 0.0326(17) -0.0072(15) 0.0054(14) 0.0173(16) F9 0.071(2) 0.062(2) 0.055(2) 0.0187(18) 0.0293(18) 0.0029(19) F10 0.062(2) 0.057(2) 0.057(2) 0.0180(17) 0.0229(17) -0.0033(17) F11 0.0463(19) 0.0358(18) 0.082(3) 0.0120(17) 0.0089(17) 0.0074(15) F12 0.053(2) 0.050(2) 0.073(3) 0.0113(18) -0.0191(19) -0.0006(16) F13 0.122(4) 0.107(4) 0.066(3) 0.040(3) 0.019(3) 0.069(3) F14 0.092(3) 0.136(4) 0.179(5) 0.117(4) 0.090(4) 0.083(3) F15 0.128(4) 0.067(3) 0.129(4) 0.053(3) 0.036(3) 0.039(3) F16 0.044(2) 0.100(3) 0.046(2) -0.006(2) 0.0098(17) -0.0134(19) F17 0.096(3) 0.050(2) 0.073(3) 0.008(2) -0.013(2) -0.031(2) F18 0.063(2) 0.082(3) 0.0312(18) 0.0109(17) 0.0032(15) -0.0038(19) F19 0.087(3) 0.057(2) 0.051(2) 0.0244(17) 0.0066(19) 0.031(2) F20 0.087(3) 0.059(2) 0.0303(18) 0.0078(16) -0.0037(17) 0.014(2) F21 0.058(2) 0.077(3) 0.051(2) 0.0318(19) 0.0183(17) 0.0032(18) F22 0.128(4) 0.045(2) 0.134(4) 0.029(2) 0.087(3) 0.038(2) F23 0.144(5) 0.037(2) 0.131(4) 0.007(2) -0.083(4) -0.013(2) F24 0.091(3) 0.045(2) 0.069(2) 0.0263(18) 0.029(2) 0.0097(19) F25 0.0425(19) 0.068(2) 0.0466(19) -0.0030(16) 0.0166(15) 0.0161(16) F26 0.0406(19) 0.062(2) 0.0435(19) -0.0038(16) 0.0003(14) -0.0031(16) F27 0.102(3) 0.070(3) 0.0333(19) 0.0096(17) 0.0000(19) 0.032(2) F28 0.0411(19) 0.072(2) 0.046(2) -0.0007(17) 0.0141(15) 0.0170(16) F29 0.0432(18) 0.059(2) 0.0393(18) -0.0030(15) 0.0016(14) -0.0050(16) F30 0.108(3) 0.058(2) 0.0376(19) 0.0147(17) 0.0048(19) 0.035(2) F31 0.214(6) 0.030(2) 0.162(5) 0.023(3) 0.140(5) 0.017(3) F32 0.084(3) 0.039(2) 0.167(5) -0.001(3) 0.014(3) 0.028(2) F33 0.192(6) 0.036(2) 0.093(4) -0.006(2) -0.055(4) 0.003(3) F34 0.081(3) 0.100(3) 0.072(3) 0.047(2) 0.038(2) 0.022(2) F35 0.143(4) 0.055(2) 0.0316(19) -0.0004(16) -0.007(2) 0.030(2) F36 0.105(3) 0.054(2) 0.0378(18) 0.0128(16) 0.0028(18) 0.037(2) C1 0.033(3) 0.029(3) 0.026(2) 0.001(2) 0.005(2) 0.012(2) C2 0.031(3) 0.018(2) 0.026(2) 0.0019(18) 0.0028(19) 0.0004(19) C3 0.033(3) 0.028(3) 0.031(3) 0.007(2) 0.009(2) 0.007(2) C4 0.025(2) 0.047(3) 0.030(3) 0.011(2) 0.002(2) 0.007(2) C5 0.032(3) 0.031(3) 0.026(2) 0.007(2) 0.004(2) 0.009(2) C6 0.036(3) 0.033(3) 0.021(2) 0.006(2) 0.004(2) 0.004(2) C7 0.029(3) 0.022(2) 0.034(3) 0.0061(19) 0.006(2) 0.0078(19) C8 0.038(3) 0.050(3) 0.024(3) 0.010(2) 0.007(2) 0.013(3) C9 0.044(2) 0.077(3) 0.035(2) 0.0195(19) -0.0009(17) 0.0206(19) C10 0.033(3) 0.051(4) 0.032(3) 0.004(3) 0.003(2) 0.012(3) C11 0.032(3) 0.043(3) 0.028(3) 0.012(2) 0.004(2) -0.001(2) C12 0.046(3) 0.042(3) 0.016(2) 0.006(2) 0.008(2) 0.011(2) C13 0.038(3) 0.031(3) 0.029(3) 0.006(2) 0.006(2) 0.010(2) C14 0.043(3) 0.044(3) 0.033(3) 0.013(2) 0.011(2) 0.018(2) C15 0.058(4) 0.039(3) 0.034(3) 0.010(2) 0.026(3) 0.018(3) C16 0.065(4) 0.043(3) 0.034(3) 0.008(2) 0.023(3) 0.009(3) C17 0.053(3) 0.036(3) 0.022(3) 0.001(2) 0.014(2) 0.000(2) C18 0.038(3) 0.041(3) 0.037(3) 0.011(2) 0.007(2) 0.009(2) C19 0.084(5) 0.044(4) 0.072(5) 0.036(3) 0.039(4) 0.031(3) C20 0.062(4) 0.049(4) 0.034(3) 0.005(3) 0.005(3) -0.012(3) C21 0.032(3) 0.039(3) 0.024(2) 0.005(2) 0.007(2) 0.010(2) C22 0.022(2) 0.034(3) 0.043(3) 0.005(2) 0.008(2) 0.010(2) C23 0.028(3) 0.033(3) 0.033(3) 0.008(2) 0.008(2) 0.008(2) C24 0.032(3) 0.039(3) 0.032(3) 0.005(2) 0.005(2) 0.010(2) C25 0.032(3) 0.029(3) 0.038(3) 0.009(2) 0.008(2) 0.004(2) C26 0.026(3) 0.040(3) 0.039(3) 0.011(2) 0.008(2) 0.009(2) C27 0.025(2) 0.033(3) 0.034(3) 0.008(2) 0.008(2) 0.006(2) C28 0.040(3) 0.044(3) 0.029(3) 0.001(2) 0.003(2) 0.010(3) C29 0.054(4) 0.038(3) 0.051(4) 0.013(3) 0.011(3) 0.009(3) C30 0.050(3) 0.044(3) 0.035(3) 0.013(3) 0.005(2) 0.012(3) C32 0.035(3) 0.032(3) 0.026(2) 0.010(2) 0.004(2) 0.006(2) C33 0.027(3) 0.035(3) 0.032(3) 0.010(2) 0.007(2) 0.008(2) C34 0.033(3) 0.032(3) 0.029(3) 0.002(2) 0.006(2) 0.005(2) C35 0.033(3) 0.035(3) 0.036(3) 0.008(2) 0.006(2) 0.006(2) C36 0.030(3) 0.028(3) 0.047(3) -0.001(2) 0.011(2) 0.007(2) C37 0.032(3) 0.042(3) 0.038(3) 0.002(2) 0.003(2) 0.008(2) C38 0.037(3) 0.036(3) 0.032(3) 0.007(2) 0.007(2) 0.011(2) C39 0.068(4) 0.047(4) 0.039(3) 0.007(3) 0.008(3) 0.018(3) C40 0.043(3) 0.045(4) 0.054(4) 0.010(3) 0.012(3) 0.008(3) C41 0.045(3) 0.037(3) 0.034(3) 0.008(2) 0.007(2) 0.012(3) _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 S1 . S2 . 2.080(2) yes S1 . N1 . 1.636(4) yes S2 . N2 . 1.642(4) yes S3 . S4 . 2.089(2) yes S3 . N3 . 1.630(5) yes S4 . N4 . 1.632(5) yes S5 . S6 . 2.082(2) yes S5 . N5 . 1.637(4) yes S6 . N6 . 1.631(4) yes S7 . S8 . 2.0863(19) yes S7 . N7 . 1.635(5) yes S8 . N8 . 1.637(4) yes N1 . C1 . 1.335(6) yes N2 . C1 . 1.320(6) yes N3 . C11 . 1.349(7) yes N4 . C11 . 1.322(6) yes N5 . C21 . 1.327(6) yes N6 . C21 . 1.324(7) yes N7 . C32 . 1.310(6) yes N8 . C32 . 1.332(6) yes F1 . C8 . 1.340(6) yes F2 . C8 . 1.345(6) yes F3 . C8 . 1.342(6) yes F4 . F40 . 0.916(10) yes F4 . F50 . 1.583(14) yes F4 . C9 . 1.300(10) yes F5 . F40 . 1.549(14) yes F5 . F60 . 0.771(10) yes F5 . C9 . 1.309(11) yes F6 . F50 . 0.733(11) yes F6 . F60 . 1.622(14) yes F6 . C9 . 1.323(10) yes F40 . C9 . 1.305(9) yes F50 . C9 . 1.294(11) yes F60 . C9 . 1.364(11) yes F7 . C10 . 1.329(6) yes F8 . C10 . 1.335(6) yes F9 . C10 . 1.339(7) yes F10 . C18 . 1.347(6) yes F11 . C18 . 1.336(6) yes F12 . C18 . 1.337(6) yes F13 . C19 . 1.324(8) yes F14 . C19 . 1.277(8) yes F15 . C19 . 1.357(8) yes F16 . C20 . 1.356(8) yes F17 . C20 . 1.329(7) yes F18 . C20 . 1.319(7) yes F19 . C30 . 1.326(7) yes F20 . C30 . 1.336(7) yes F21 . C30 . 1.329(7) yes F22 . C29 . 1.330(7) yes F23 . C29 . 1.302(7) yes F24 . C29 . 1.321(7) yes F25 . C28 . 1.337(6) yes F26 . C28 . 1.319(6) yes F27 . C28 . 1.332(6) yes F28 . C41 . 1.316(6) yes F29 . C41 . 1.350(6) yes F30 . C41 . 1.311(6) yes F31 . C40 . 1.291(7) yes F32 . C40 . 1.320(7) yes F33 . C40 . 1.311(8) yes F34 . C39 . 1.323(8) yes F35 . C39 . 1.341(7) yes F36 . C39 . 1.337(7) yes C1 . C2 . 1.498(7) yes C2 . C3 . 1.403(7) yes C2 . C7 . 1.392(7) yes C3 . C4 . 1.394(7) yes C3 . C10 . 1.502(7) yes C4 . C5 . 1.377(7) yes C4 . H41 . 1.013 no C5 . C6 . 1.385(7) yes C5 . C9 . 1.487(7) yes C6 . C7 . 1.389(7) yes C6 . H61 . 1.017 no C7 . C8 . 1.492(7) yes C11 . C12 . 1.491(7) yes C12 . C13 . 1.408(7) yes C12 . C17 . 1.383(7) yes C13 . C14 . 1.391(7) yes C13 . C18 . 1.496(7) yes C14 . C15 . 1.389(8) yes C14 . H141 . 1.017 no C15 . C16 . 1.384(9) yes C15 . C19 . 1.497(8) yes C16 . C17 . 1.377(8) yes C16 . H161 . 1.016 no C17 . C20 . 1.510(8) yes C21 . C22 . 1.498(7) yes C22 . C23 . 1.401(7) yes C22 . C27 . 1.412(7) yes C23 . C24 . 1.388(7) yes C23 . C30 . 1.512(7) yes C24 . C25 . 1.383(7) yes C24 . H241 . 1.018 no C25 . C26 . 1.380(7) yes C25 . C29 . 1.491(7) yes C26 . C27 . 1.390(7) yes C26 . H261 . 1.015 no C27 . C28 . 1.502(7) yes C32 . C33 . 1.502(7) yes C33 . C34 . 1.394(7) yes C33 . C38 . 1.393(7) yes C34 . C35 . 1.385(7) yes C34 . C41 . 1.521(7) yes C35 . C36 . 1.389(7) yes C35 . H351 . 1.015 no C36 . C37 . 1.379(8) yes C36 . C40 . 1.481(8) yes C37 . C38 . 1.386(7) yes C37 . H371 . 1.013 no C38 . C39 . 1.500(8) yes 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 S2 . S1 . N1 . 94.55(16) yes S1 . S2 . N2 . 94.54(16) yes S4 . S3 . N3 . 94.63(17) yes S3 . S4 . N4 . 94.78(17) yes S6 . S5 . N5 . 94.42(16) yes S5 . S6 . N6 . 94.66(17) yes S8 . S7 . N7 . 94.38(17) yes S7 . S8 . N8 . 94.37(16) yes S1 . N1 . C1 . 113.6(3) yes S2 . N2 . C1 . 113.7(3) yes S3 . N3 . C11 . 113.2(4) yes S4 . N4 . C11 . 113.5(4) yes S5 . N5 . C21 . 113.3(4) yes S6 . N6 . C21 . 113.4(4) yes S7 . N7 . C32 . 113.8(4) yes S8 . N8 . C32 . 113.2(4) yes F40 . F4 . F50 . 112.7(10) yes F40 . F4 . C9 . 69.7(8) yes F50 . F4 . C9 . 52.2(5) yes F40 . F5 . F60 . 123.8(15) yes F40 . F5 . C9 . 53.6(6) yes F60 . F5 . C9 . 77.2(11) yes F50 . F6 . F60 . 119.3(14) yes F50 . F6 . C9 . 71.6(11) yes F60 . F6 . C9 . 54.0(5) yes F5 . F40 . F4 . 120.2(9) yes F5 . F40 . C9 . 53.8(5) yes F4 . F40 . C9 . 69.1(8) yes F4 . F50 . F6 . 125.3(15) yes F4 . F50 . C9 . 52.6(6) yes F6 . F50 . C9 . 75.9(12) yes F6 . F60 . F5 . 117.0(13) yes F6 . F60 . C9 . 51.7(5) yes F5 . F60 . C9 . 69.4(11) yes N1 . C1 . N2 . 123.6(4) yes N1 . C1 . C2 . 117.5(4) yes N2 . C1 . C2 . 118.9(4) yes C1 . C2 . C3 . 119.5(4) yes C1 . C2 . C7 . 122.0(4) yes C3 . C2 . C7 . 118.5(4) yes C2 . C3 . C4 . 120.3(4) yes C2 . C3 . C10 . 122.2(4) yes C4 . C3 . C10 . 117.5(4) yes C3 . C4 . C5 . 120.4(4) yes C3 . C4 . H41 . 119.412 no C5 . C4 . H41 . 120.186 no C4 . C5 . C6 . 119.7(4) yes C4 . C5 . C9 . 120.0(5) yes C6 . C5 . C9 . 120.3(4) yes C5 . C6 . C7 . 120.4(4) yes C5 . C6 . H61 . 120.019 no C7 . C6 . H61 . 119.545 no C2 . C7 . C6 . 120.6(4) yes C2 . C7 . C8 . 121.7(4) yes C6 . C7 . C8 . 117.7(4) yes C7 . C8 . F2 . 113.3(4) yes C7 . C8 . F3 . 112.4(4) yes F2 . C8 . F3 . 105.6(4) yes C7 . C8 . F1 . 112.6(4) yes F2 . C8 . F1 . 106.6(4) yes F3 . C8 . F1 . 105.8(4) yes C5 . C9 . F60 . 110.8(6) yes C5 . C9 . F6 . 112.0(6) yes F60 . C9 . F6 . 74.2(7) yes C5 . C9 . F5 . 110.4(6) yes F60 . C9 . F5 . 33.4(5) yes F6 . C9 . F5 . 105.0(7) yes C5 . C9 . F40 . 115.7(6) yes F60 . C9 . F40 . 102.3(7) yes F6 . C9 . F40 . 129.7(7) yes F5 . C9 . F40 . 72.7(7) yes C5 . C9 . F4 . 111.6(6) yes F60 . C9 . F4 . 133.6(7) yes F6 . C9 . F4 . 105.9(7) yes F5 . C9 . F4 . 111.7(8) yes F40 . C9 . F4 . 41.2(5) yes C5 . C9 . F50 . 114.8(7) yes F60 . C9 . F50 . 103.0(8) yes F6 . C9 . F50 . 32.5(5) yes F5 . C9 . F50 . 127.2(8) yes F40 . C9 . F50 . 108.8(8) yes F4 . C9 . F50 . 75.2(8) yes C3 . C10 . F9 . 112.2(4) yes C3 . C10 . F8 . 112.9(4) yes F9 . C10 . F8 . 106.6(4) yes C3 . C10 . F7 . 111.9(4) yes F9 . C10 . F7 . 106.4(4) yes F8 . C10 . F7 . 106.4(4) yes N3 . C11 . N4 . 123.8(5) yes N3 . C11 . C12 . 118.2(4) yes N4 . C11 . C12 . 118.0(5) yes C11 . C12 . C13 . 119.4(5) yes C11 . C12 . C17 . 121.7(5) yes C13 . C12 . C17 . 119.0(5) yes C12 . C13 . C14 . 120.1(5) yes C12 . C13 . C18 . 122.7(5) yes C14 . C13 . C18 . 117.2(5) yes C13 . C14 . C15 . 119.6(5) yes C13 . C14 . H141 . 120.488 no C15 . C14 . H141 . 119.922 no C14 . C15 . C16 . 120.2(5) yes C14 . C15 . C19 . 117.7(6) yes C16 . C15 . C19 . 122.1(6) yes C15 . C16 . C17 . 120.2(5) yes C15 . C16 . H161 . 119.653 no C17 . C16 . H161 . 120.106 no C12 . C17 . C16 . 120.9(5) yes C12 . C17 . C20 . 121.2(5) yes C16 . C17 . C20 . 117.9(5) yes C13 . C18 . F10 . 112.4(4) yes C13 . C18 . F12 . 112.3(4) yes F10 . C18 . F12 . 105.5(4) yes C13 . C18 . F11 . 113.6(4) yes F10 . C18 . F11 . 105.9(4) yes F12 . C18 . F11 . 106.5(4) yes C15 . C19 . F15 . 111.1(6) yes C15 . C19 . F13 . 112.3(5) yes F15 . C19 . F13 . 102.5(5) yes C15 . C19 . F14 . 113.7(5) yes F15 . C19 . F14 . 105.4(6) yes F13 . C19 . F14 . 111.0(7) yes C17 . C20 . F16 . 111.5(5) yes C17 . C20 . F17 . 112.3(6) yes F16 . C20 . F17 . 106.0(5) yes C17 . C20 . F18 . 112.8(5) yes F16 . C20 . F18 . 106.1(5) yes F17 . C20 . F18 . 107.7(5) yes N5 . C21 . N6 . 124.1(5) yes N5 . C21 . C22 . 118.4(4) yes N6 . C21 . C22 . 117.5(4) yes C21 . C22 . C23 . 120.3(5) yes C21 . C22 . C27 . 121.4(4) yes C23 . C22 . C27 . 118.3(4) yes C22 . C23 . C24 . 120.6(5) yes C22 . C23 . C30 . 122.3(5) yes C24 . C23 . C30 . 117.0(4) yes C23 . C24 . C25 . 120.2(5) yes C23 . C24 . H241 . 119.694 no C25 . C24 . H241 . 120.124 no C24 . C25 . C26 . 120.4(5) yes C24 . C25 . C29 . 118.8(5) yes C26 . C25 . C29 . 120.8(5) yes C25 . C26 . C27 . 120.1(5) yes C25 . C26 . H261 . 120.513 no C27 . C26 . H261 . 119.371 no C22 . C27 . C26 . 120.4(5) yes C22 . C27 . C28 . 120.8(4) yes C26 . C27 . C28 . 118.8(4) yes C27 . C28 . F25 . 112.3(4) yes C27 . C28 . F27 . 111.1(4) yes F25 . C28 . F27 . 106.4(4) yes C27 . C28 . F26 . 113.7(4) yes F25 . C28 . F26 . 107.2(4) yes F27 . C28 . F26 . 105.7(4) yes C25 . C29 . F22 . 112.1(5) yes C25 . C29 . F24 . 113.9(5) yes F22 . C29 . F24 . 104.2(5) yes C25 . C29 . F23 . 112.2(5) yes F22 . C29 . F23 . 107.8(6) yes F24 . C29 . F23 . 106.1(5) yes C23 . C30 . F20 . 111.2(5) yes C23 . C30 . F21 . 112.6(4) yes F20 . C30 . F21 . 106.5(5) yes C23 . C30 . F19 . 112.8(4) yes F20 . C30 . F19 . 106.1(5) yes F21 . C30 . F19 . 107.2(5) yes N8 . C32 . N7 . 124.3(5) yes N8 . C32 . C33 . 117.5(4) yes N7 . C32 . C33 . 118.2(4) yes C32 . C33 . C34 . 120.6(4) yes C32 . C33 . C38 . 120.8(4) yes C34 . C33 . C38 . 118.7(5) yes C33 . C34 . C35 . 120.9(4) yes C33 . C34 . C41 . 122.0(4) yes C35 . C34 . C41 . 117.0(4) yes C34 . C35 . C36 . 119.5(5) yes C34 . C35 . H351 . 120.624 no C36 . C35 . H351 . 119.907 no C35 . C36 . C37 . 120.3(5) yes C35 . C36 . C40 . 119.7(5) yes C37 . C36 . C40 . 119.9(5) yes C36 . C37 . C38 . 120.1(5) yes C36 . C37 . H371 . 119.693 no C38 . C37 . H371 . 120.213 no C33 . C38 . C37 . 120.6(5) yes C33 . C38 . C39 . 121.9(5) yes C37 . C38 . C39 . 117.5(5) yes C38 . C39 . F35 . 111.7(5) yes C38 . C39 . F36 . 112.7(5) yes F35 . C39 . F36 . 106.0(5) yes C38 . C39 . F34 . 112.5(5) yes F35 . C39 . F34 . 106.6(5) yes F36 . C39 . F34 . 106.9(5) yes C36 . C40 . F32 . 113.3(5) yes C36 . C40 . F33 . 114.2(5) yes F32 . C40 . F33 . 102.6(6) yes C36 . C40 . F31 . 114.1(5) yes F32 . C40 . F31 . 104.0(6) yes F33 . C40 . F31 . 107.5(6) yes C34 . C41 . F29 . 111.5(4) yes C34 . C41 . F28 . 112.6(4) yes F29 . C41 . F28 . 105.5(4) yes C34 . C41 . F30 . 112.2(4) yes F29 . C41 . F30 . 105.7(4) yes F28 . C41 . F30 . 108.9(4) yes data_jr0113 _database_code_depnum_ccdc_archive 'CCDC 274779' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H2 F9 N2 S2' _chemical_formula_weight 385.26 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' F F 0.0171 0.0103 '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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pna2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, z' _cell_length_a 17.6507(6) _cell_length_b 7.9712(3) _cell_length_c 19.0992(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2687.21(16) _cell_formula_units_Z 8 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 12749 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour ? _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.905 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1512 _exptl_absorpt_coefficient_mu 0.501 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.979 _exptl_absorpt_correction_T_max 1.029 _exptl_absorpt_process_details 'Sortav Blessing (1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_standards_number 0 _diffrn_reflns_number 18493 _diffrn_reflns_av_R_equivalents 0.0531 _diffrn_reflns_av_sigmaI/netI 0.0640 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 3.52 _diffrn_reflns_theta_max 27.49 _reflns_number_total 6056 _reflns_number_gt 4174 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SHELXS-97 (Sheldrick 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. All CF~3~ groups exhibit considerable disorder. Each of these groups was modelled as disordered over two sites, all C-F distances were restrained to a common target value (1.30(2)A) and the geometry of each site was restrained to be tetrahedral. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0563P)^2^+0.0000P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.01(7) _refine_ls_number_reflns 6056 _refine_ls_number_parameters 578 _refine_ls_number_restraints 73 _refine_ls_R_factor_all 0.0813 _refine_ls_R_factor_gt 0.0466 _refine_ls_wR_factor_ref 0.1104 _refine_ls_wR_factor_gt 0.0967 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.042 _refine_ls_shift/su_max 0.009 _refine_ls_shift/su_mean 0.001 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 S11 S -0.00937(6) 1.26373(14) 0.79565(6) 0.0492(3) Uani 1 1 d . . . S12 S -0.07307(6) 1.1662(2) 0.71567(7) 0.0856(5) Uani 1 1 d . . . N11 N 0.07077(17) 1.1906(4) 0.76515(19) 0.0456(9) Uani 1 1 d . . . N12 N -0.0009(2) 1.0817(6) 0.67465(18) 0.0713(12) Uani 1 1 d . . . C10 C 0.06416(18) 1.1063(5) 0.70629(18) 0.0321(8) Uani 1 1 d . . . C11 C 0.13377(17) 1.0244(4) 0.67756(16) 0.0288(7) Uani 1 1 d . . . C12 C 0.18165(19) 1.1085(5) 0.63098(19) 0.0319(8) Uani 1 1 d . B . C13 C 0.24859(19) 1.0337(5) 0.60818(19) 0.0378(8) Uani 1 1 d . . . H13A H 0.2805 1.0908 0.5760 0.045 Uiso 1 1 calc R . . C14 C 0.2684(2) 0.8768(5) 0.63235(19) 0.0358(8) Uani 1 1 d . A . C15 C 0.2210(2) 0.7895(4) 0.67734(19) 0.0348(8) Uani 1 1 d . . . H15A H 0.2342 0.6801 0.6928 0.042 Uiso 1 1 calc R . . C16 C 0.15343(19) 0.8642(4) 0.69966(17) 0.0301(8) Uani 1 1 d . C . C17 C 0.3422(3) 0.7982(6) 0.6111(2) 0.0597(13) Uani 1 1 d D . . F17A F 0.3976(5) 0.8746(15) 0.6477(6) 0.115(5) Uani 0.50 1 d PD A 1 F17B F 0.3618(9) 0.8176(19) 0.5477(4) 0.114(8) Uani 0.50 1 d PD A 1 F17C F 0.3499(7) 0.6452(11) 0.6308(7) 0.102(4) Uani 0.50 1 d PD A 1 F17D F 0.3875(7) 0.771(2) 0.6603(5) 0.135(8) Uani 0.50 1 d PD A 2 F17E F 0.3747(6) 0.8809(16) 0.5617(5) 0.078(4) Uani 0.50 1 d PD A 2 F17F F 0.3299(6) 0.6510(12) 0.5786(9) 0.139(5) Uani 0.50 1 d PD A 2 C18 C 0.1651(2) 1.2812(5) 0.6041(2) 0.0432(10) Uani 1 1 d D . . F18A F 0.1078(5) 1.2889(11) 0.5608(5) 0.091(3) Uani 0.50 1 d PD B 1 F18B F 0.2228(5) 1.3533(12) 0.5719(6) 0.103(4) Uani 0.50 1 d PD B 1 F18C F 0.1475(6) 1.3903(11) 0.6538(4) 0.078(3) Uani 0.50 1 d PD B 1 F18D F 0.0917(3) 1.3111(11) 0.6001(5) 0.071(3) Uani 0.50 1 d PD B 2 F18E F 0.1910(5) 1.3031(11) 0.5401(3) 0.071(3) Uani 0.50 1 d PD B 2 F18F F 0.1947(6) 1.3912(11) 0.6443(5) 0.097(4) Uani 0.50 1 d PD B 2 C19 C 0.1042(2) 0.7634(5) 0.7490(2) 0.0478(11) Uani 1 1 d D . . F19A F 0.0314(3) 0.7886(11) 0.7395(4) 0.076(2) Uani 0.50 1 d PD C 1 F19B F 0.1162(5) 0.8248(14) 0.8140(4) 0.080(3) Uani 0.50 1 d PD C 1 F19C F 0.1201(7) 0.6039(10) 0.7551(9) 0.104(6) Uani 0.50 1 d PD C 1 F19D F 0.0451(4) 0.6922(9) 0.7149(4) 0.0669(18) Uani 0.50 1 d PD C 2 F19E F 0.0793(5) 0.8454(11) 0.8028(5) 0.072(3) Uani 0.50 1 d PD C 2 F19F F 0.1423(6) 0.6317(9) 0.7720(6) 0.057(2) Uani 0.50 1 d PD C 2 S22 S 0.25917(5) 0.68954(14) 0.31667(6) 0.0468(3) Uani 1 1 d . . . S21 S 0.32582(5) 0.82503(14) 0.38611(6) 0.0489(3) Uani 1 1 d . . . N21 N 0.25417(16) 0.9188(4) 0.42441(16) 0.0421(8) Uani 1 1 d . . . N22 N 0.17870(16) 0.7644(4) 0.34638(18) 0.0383(7) Uani 1 1 d . . . C20 C 0.18840(18) 0.8753(4) 0.39721(17) 0.0303(7) Uani 1 1 d . . . C21 C 0.11822(16) 0.9639(4) 0.42414(16) 0.0271(7) Uani 1 1 d . . . C22 C 0.06852(19) 0.8851(4) 0.47143(18) 0.0293(7) Uani 1 1 d . E . C23 C 0.0029(2) 0.9636(5) 0.49153(18) 0.0370(8) Uani 1 1 d . . . H23A H -0.0300 0.9098 0.5238 0.044 Uiso 1 1 calc R . . C24 C -0.0160(2) 1.1191(5) 0.46560(19) 0.0357(8) Uani 1 1 d . D . C25 C 0.0332(2) 1.2018(4) 0.42058(19) 0.0349(8) Uani 1 1 d . . . H25A H 0.0213 1.3109 0.4039 0.042 Uiso 1 1 calc R . . C26 C 0.1002(2) 1.1236(4) 0.40006(18) 0.0315(8) Uani 1 1 d . F . C27 C -0.0901(3) 1.1980(6) 0.4848(2) 0.0570(13) Uani 1 1 d D . . F27A F -0.1465(5) 1.1147(16) 0.4549(5) 0.083(4) Uani 0.50 1 d PD D 1 F27B F -0.0953(10) 1.3529(13) 0.4643(9) 0.132(8) Uani 0.50 1 d PD D 1 F27C F -0.1072(8) 1.193(2) 0.5516(4) 0.082(3) Uani 0.50 1 d PD D 1 F27D F -0.0854(9) 1.248(2) 0.5504(4) 0.157(9) Uani 0.50 1 d PD D 2 F27E F -0.1487(6) 1.1019(14) 0.4787(9) 0.145(8) Uani 0.50 1 d PD D 2 F27F F -0.1034(7) 1.3380(11) 0.4513(5) 0.065(3) Uani 0.50 1 d PD D 2 C28 C 0.0844(2) 0.7126(5) 0.49980(19) 0.0384(9) Uani 1 1 d D . . F28A F 0.0712(12) 0.5908(18) 0.4558(6) 0.071(4) Uani 0.50 1 d PD E 1 F28B F 0.1554(4) 0.696(2) 0.5201(7) 0.066(4) Uani 0.50 1 d PD E 1 F28C F 0.0439(6) 0.6728(18) 0.5558(5) 0.089(5) Uani 0.50 1 d PD E 1 F28D F 0.0531(7) 0.6972(19) 0.5617(4) 0.066(4) Uani 0.50 1 d PD E 2 F28E F 0.1566(4) 0.6773(18) 0.5072(8) 0.073(4) Uani 0.50 1 d PD E 2 F28F F 0.0546(12) 0.600(2) 0.4585(9) 0.096(7) Uani 0.50 1 d PD E 2 C29 C 0.1519(2) 1.2220(5) 0.3528(2) 0.0434(10) Uani 1 1 d D . . F29A F 0.1754(11) 1.126(2) 0.3004(7) 0.105(7) Uani 0.50 1 d PD F 1 F29B F 0.1180(6) 1.3520(11) 0.3245(7) 0.064(5) Uani 0.50 1 d PD F 1 F29C F 0.2141(9) 1.276(2) 0.3842(10) 0.101(7) Uani 0.50 1 d PD F 1 F29D F 0.1859(8) 1.1324(15) 0.3031(5) 0.053(3) Uani 0.50 1 d PD F 2 F29E F 0.2071(7) 1.2931(17) 0.3896(8) 0.065(4) Uani 0.50 1 d PD F 2 F29F F 0.1167(8) 1.3432(15) 0.3195(6) 0.069(5) Uani 0.50 1 d PD F 2 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 S11 0.0323(5) 0.0631(6) 0.0521(6) -0.0184(5) 0.0060(5) 0.0048(4) S12 0.0283(5) 0.1656(16) 0.0630(8) -0.0487(10) -0.0079(6) 0.0244(7) N11 0.0269(17) 0.059(2) 0.051(2) -0.0253(17) 0.0022(15) -0.0006(14) N12 0.0326(18) 0.130(4) 0.051(2) -0.039(2) -0.0075(17) 0.017(2) C10 0.0283(18) 0.040(2) 0.0279(17) 0.0011(16) 0.0004(15) -0.0006(15) C11 0.0249(16) 0.036(2) 0.0251(16) -0.0046(15) 0.0013(14) -0.0001(14) C12 0.0294(19) 0.037(2) 0.0293(17) 0.0000(15) 0.0027(15) 0.0006(15) C13 0.0304(17) 0.050(2) 0.0334(17) 0.0036(18) 0.0086(16) 0.0008(16) C14 0.037(2) 0.038(2) 0.0328(18) -0.0031(16) 0.0022(16) 0.0064(16) C15 0.036(2) 0.035(2) 0.0331(19) 0.0002(16) -0.0015(17) 0.0019(15) C16 0.0303(18) 0.035(2) 0.0248(17) 0.0014(14) -0.0027(14) -0.0023(14) C17 0.040(3) 0.074(4) 0.065(3) 0.007(3) 0.015(3) 0.019(2) F17A 0.031(4) 0.177(12) 0.137(11) -0.045(8) -0.019(5) 0.041(5) F17B 0.131(12) 0.183(17) 0.029(3) 0.004(6) 0.020(5) 0.111(12) F17C 0.093(8) 0.096(8) 0.116(9) 0.039(7) 0.045(7) 0.059(6) F17D 0.097(10) 0.25(2) 0.058(5) 0.045(10) 0.013(5) 0.121(12) F17E 0.045(4) 0.099(7) 0.090(8) 0.029(6) 0.045(5) 0.033(4) F17F 0.108(8) 0.065(6) 0.245(14) -0.065(8) 0.091(10) 0.002(5) C18 0.040(2) 0.043(2) 0.047(2) 0.009(2) 0.014(2) 0.0040(18) F18A 0.121(9) 0.064(5) 0.089(6) 0.021(5) -0.068(6) 0.000(5) F18B 0.073(5) 0.084(7) 0.153(10) 0.063(7) 0.070(6) 0.026(4) F18C 0.149(8) 0.031(4) 0.054(4) 0.001(3) 0.010(6) 0.024(5) F18D 0.051(3) 0.069(5) 0.094(6) 0.041(5) 0.012(5) 0.021(3) F18E 0.101(8) 0.063(5) 0.049(4) 0.030(3) 0.030(4) 0.025(4) F18F 0.161(10) 0.034(4) 0.095(8) -0.017(4) -0.047(8) -0.012(6) C19 0.046(3) 0.060(3) 0.038(2) 0.010(2) 0.002(2) -0.001(2) F19A 0.036(3) 0.095(6) 0.098(6) 0.035(5) 0.001(4) -0.018(4) F19B 0.080(6) 0.118(7) 0.040(3) 0.010(4) 0.028(4) -0.016(5) F19C 0.113(10) 0.027(4) 0.172(13) 0.004(5) 0.069(9) -0.015(5) F19D 0.049(4) 0.075(5) 0.077(4) 0.018(4) -0.002(3) -0.028(4) F19E 0.092(7) 0.053(4) 0.071(6) 0.003(4) 0.056(5) 0.003(4) F19F 0.055(4) 0.038(5) 0.077(4) 0.032(4) 0.011(3) -0.004(4) S22 0.0326(5) 0.0553(6) 0.0525(6) -0.0193(5) 0.0035(5) 0.0093(4) S21 0.0272(5) 0.0641(7) 0.0555(6) -0.0167(6) 0.0017(5) 0.0053(4) N21 0.0261(15) 0.055(2) 0.0454(17) -0.0142(16) 0.0002(15) 0.0066(14) N22 0.0278(16) 0.0457(19) 0.0414(17) -0.0096(14) 0.0001(14) 0.0070(13) C20 0.0273(17) 0.0340(18) 0.0295(18) 0.0040(15) 0.0025(14) 0.0020(13) C21 0.0239(15) 0.0305(19) 0.0270(16) -0.0037(15) -0.0028(14) -0.0003(13) C22 0.0310(19) 0.0260(18) 0.0309(18) 0.0004(15) -0.0002(15) -0.0014(14) C23 0.0313(18) 0.045(2) 0.0352(17) -0.0003(17) 0.0061(16) -0.0036(16) C24 0.0335(18) 0.040(2) 0.0336(18) -0.0037(16) 0.0013(16) 0.0076(16) C25 0.043(2) 0.0279(19) 0.0338(18) -0.0014(15) -0.0033(18) 0.0075(16) C26 0.0320(18) 0.0305(19) 0.0320(17) -0.0039(15) 0.0015(15) -0.0020(14) C27 0.053(3) 0.064(3) 0.054(3) 0.007(3) 0.015(3) 0.025(3) F27A 0.025(4) 0.154(11) 0.069(4) -0.029(5) -0.012(3) 0.013(5) F27B 0.102(10) 0.081(9) 0.212(18) 0.018(9) 0.083(11) 0.027(7) F27C 0.052(5) 0.155(8) 0.039(5) 0.017(5) 0.022(4) 0.048(5) F27D 0.139(14) 0.28(2) 0.048(6) -0.034(8) 0.007(6) 0.158(13) F27E 0.061(7) 0.081(7) 0.29(2) 0.033(10) 0.085(10) 0.023(5) F27F 0.064(6) 0.079(7) 0.051(4) 0.015(4) 0.002(4) 0.061(5) C28 0.037(2) 0.039(2) 0.039(2) 0.0020(18) 0.0051(19) 0.0041(17) F28A 0.137(10) 0.028(6) 0.048(6) 0.004(4) -0.023(5) 0.006(5) F28B 0.041(6) 0.085(8) 0.073(5) 0.021(5) -0.038(5) 0.005(5) F28C 0.069(6) 0.064(7) 0.135(11) 0.063(7) 0.072(6) 0.037(5) F28D 0.102(8) 0.067(7) 0.029(4) 0.015(4) 0.007(4) -0.004(5) F28E 0.052(6) 0.041(5) 0.127(10) 0.045(6) 0.037(5) 0.017(4) F28F 0.147(12) 0.032(7) 0.110(11) 0.000(6) -0.050(9) -0.024(7) C29 0.048(3) 0.038(3) 0.044(2) 0.004(2) 0.010(2) -0.0006(19) F29A 0.155(14) 0.075(10) 0.085(11) -0.003(8) 0.077(9) -0.005(8) F29B 0.061(8) 0.025(6) 0.107(10) 0.022(5) 0.043(6) 0.002(5) F29C 0.061(8) 0.131(12) 0.112(14) 0.054(10) 0.004(8) -0.014(7) F29D 0.056(4) 0.048(7) 0.054(7) 0.023(5) 0.025(4) 0.007(4) F29E 0.054(6) 0.067(6) 0.072(8) 0.009(6) -0.013(6) -0.047(5) F29F 0.081(10) 0.079(10) 0.048(6) 0.036(6) -0.012(5) 0.014(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 S11 N11 1.637(3) . ? S11 S12 2.0498(16) . ? S12 N12 1.640(4) . ? N11 C10 1.315(5) . ? N12 C10 1.313(5) . ? C10 C11 1.496(4) . ? C11 C16 1.389(5) . ? C11 C12 1.398(5) . ? C12 C13 1.393(5) . ? C12 C18 1.499(5) . ? C13 C14 1.379(5) . ? C13 H13A 0.9500 . ? C14 C15 1.388(5) . ? C14 C17 1.501(6) . ? C15 C16 1.399(5) . ? C15 H15A 0.9500 . ? C16 C19 1.513(5) . ? C17 F17D 1.253(8) . ? C17 F17B 1.269(8) . ? C17 F17C 1.284(7) . ? C17 F17E 1.285(8) . ? C17 F17F 1.345(7) . ? C17 F17A 1.347(8) . ? C18 F18F 1.277(7) . ? C18 F18A 1.307(7) . ? C18 F18E 1.317(6) . ? C18 F18D 1.319(7) . ? C18 F18B 1.321(7) . ? C18 F18C 1.324(7) . ? C19 F19E 1.294(7) . ? C19 F19C 1.308(8) . ? C19 F19A 1.313(6) . ? C19 F19F 1.322(7) . ? C19 F19B 1.351(8) . ? C19 F19D 1.354(6) . ? S22 N22 1.642(3) . ? S22 S21 2.0759(14) . ? S21 N21 1.641(3) . ? N21 C20 1.318(4) . ? N22 C20 1.324(5) . ? C20 C21 1.516(4) . ? C21 C26 1.391(5) . ? C21 C22 1.407(5) . ? C22 C23 1.372(5) . ? C22 C28 1.504(5) . ? C23 C24 1.376(5) . ? C23 H23A 0.9500 . ? C24 C25 1.388(5) . ? C24 C27 1.498(6) . ? C25 C26 1.392(5) . ? C25 H25A 0.9500 . ? C26 C29 1.504(5) . ? C27 F27E 1.292(8) . ? C27 F27B 1.299(8) . ? C27 F27F 1.307(7) . ? C27 F27C 1.310(8) . ? C27 F27D 1.316(8) . ? C27 F27A 1.326(8) . ? C28 F28F 1.303(8) . ? C28 F28A 1.305(8) . ? C28 F28D 1.310(7) . ? C28 F28E 1.312(8) . ? C28 F28B 1.319(7) . ? C28 F28C 1.325(8) . ? C29 F29F 1.313(7) . ? C29 F29B 1.313(7) . ? C29 F29C 1.323(9) . ? C29 F29A 1.326(8) . ? C29 F29E 1.327(7) . ? C29 F29D 1.331(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 N11 S11 S12 94.23(13) . . ? N12 S12 S11 94.93(13) . . ? C10 N11 S11 114.2(3) . . ? C10 N12 S12 113.5(3) . . ? N12 C10 N11 123.2(3) . . ? N12 C10 C11 119.0(3) . . ? N11 C10 C11 117.6(3) . . ? C16 C11 C12 118.9(3) . . ? C16 C11 C10 119.7(3) . . ? C12 C11 C10 121.4(3) . . ? C13 C12 C11 120.4(3) . . ? C13 C12 C18 116.8(3) . . ? C11 C12 C18 122.7(3) . . ? C14 C13 C12 119.9(3) . . ? C14 C13 H13A 120.0 . . ? C12 C13 H13A 120.0 . . ? C13 C14 C15 120.6(3) . . ? C13 C14 C17 120.6(3) . . ? C15 C14 C17 118.8(3) . . ? C14 C15 C16 119.3(3) . . ? C14 C15 H15A 120.3 . . ? C16 C15 H15A 120.3 . . ? C11 C16 C15 120.8(3) . . ? C11 C16 C19 122.3(3) . . ? C15 C16 C19 117.0(3) . . ? F17D C17 F17B 124.2(10) . . ? F17D C17 F17C 62.9(8) . . ? F17B C17 F17C 111.5(8) . . ? F17D C17 F17E 110.8(9) . . ? F17B C17 F17E 27.9(10) . . ? F17C C17 F17E 130.9(8) . . ? F17D C17 F17F 107.2(9) . . ? F17B C17 F17F 73.2(9) . . ? F17C C17 F17F 47.4(7) . . ? F17E C17 F17F 100.5(7) . . ? F17D C17 F17A 39.4(8) . . ? F17B C17 F17A 104.0(9) . . ? F17C C17 F17A 101.5(7) . . ? F17E C17 F17A 79.9(9) . . ? F17F C17 F17A 138.7(8) . . ? F17D C17 C14 115.1(7) . . ? F17B C17 C14 116.4(8) . . ? F17C C17 C14 114.1(6) . . ? F17E C17 C14 111.8(7) . . ? F17F C17 C14 110.4(6) . . ? F17A C17 C14 107.5(6) . . ? F18F C18 F18A 131.7(7) . . ? F18F C18 F18E 109.0(7) . . ? F18A C18 F18E 71.1(6) . . ? F18F C18 F18D 108.2(7) . . ? F18A C18 F18D 36.5(4) . . ? F18E C18 F18D 105.3(6) . . ? F18F C18 F18B 70.5(7) . . ? F18A C18 F18B 106.3(7) . . ? F18E C18 F18B 40.7(5) . . ? F18D C18 F18B 130.7(6) . . ? F18F C18 F18C 38.2(5) . . ? F18A C18 F18C 104.0(6) . . ? F18E C18 F18C 131.3(7) . . ? F18D C18 F18C 72.1(6) . . ? F18B C18 F18C 103.2(6) . . ? F18F C18 C12 110.2(6) . . ? F18A C18 C12 114.2(5) . . ? F18E C18 C12 111.8(5) . . ? F18D C18 C12 112.2(5) . . ? F18B C18 C12 114.1(5) . . ? F18C C18 C12 113.8(5) . . ? F19E C19 F19C 119.6(10) . . ? F19E C19 F19A 72.5(6) . . ? F19C C19 F19A 111.8(7) . . ? F19E C19 F19F 108.1(7) . . ? F19C C19 F19F 24.3(8) . . ? F19A C19 F19F 131.7(7) . . ? F19E C19 F19B 30.8(5) . . ? F19C C19 F19B 103.7(9) . . ? F19A C19 F19B 103.0(6) . . ? F19F C19 F19B 84.4(8) . . ? F19E C19 F19D 109.4(6) . . ? F19C C19 F19D 78.5(7) . . ? F19A C19 F19D 41.0(4) . . ? F19F C19 F19D 102.6(6) . . ? F19B C19 F19D 135.6(6) . . ? F19E C19 C16 114.9(5) . . ? F19C C19 C16 116.6(8) . . ? F19A C19 C16 113.3(4) . . ? F19F C19 C16 109.6(6) . . ? F19B C19 C16 106.9(5) . . ? F19D C19 C16 111.4(4) . . ? N22 S22 S21 94.62(13) . . ? N21 S21 S22 94.88(12) . . ? C20 N21 S21 112.5(3) . . ? C20 N22 S22 112.6(2) . . ? N21 C20 N22 125.3(3) . . ? N21 C20 C21 117.6(3) . . ? N22 C20 C21 117.0(3) . . ? C26 C21 C22 118.6(3) . . ? C26 C21 C20 120.1(3) . . ? C22 C21 C20 121.3(3) . . ? C23 C22 C21 120.2(3) . . ? C23 C22 C28 118.3(3) . . ? C21 C22 C28 121.5(3) . . ? C22 C23 C24 121.0(3) . . ? C22 C23 H23A 119.5 . . ? C24 C23 H23A 119.5 . . ? C23 C24 C25 120.0(3) . . ? C23 C24 C27 120.1(3) . . ? C25 C24 C27 120.0(3) . . ? C24 C25 C26 119.5(3) . . ? C24 C25 H25A 120.2 . . ? C26 C25 H25A 120.2 . . ? C21 C26 C25 120.7(3) . . ? C21 C26 C29 122.5(3) . . ? C25 C26 C29 116.8(3) . . ? F27E C27 F27B 118.7(11) . . ? F27E C27 F27F 108.6(9) . . ? F27B C27 F27F 13.6(12) . . ? F27E C27 F27C 83.6(10) . . ? F27B C27 F27C 107.8(10) . . ? F27F C27 F27C 117.4(11) . . ? F27E C27 F27D 108.5(10) . . ? F27B C27 F27D 90.2(13) . . ? F27F C27 F27D 102.6(9) . . ? F27C C27 F27D 25.6(12) . . ? F27E C27 F27A 20.5(10) . . ? F27B C27 F27A 107.0(9) . . ? F27F C27 F27A 94.7(9) . . ? F27C C27 F27A 103.5(8) . . ? F27D C27 F27A 127.6(10) . . ? F27E C27 C24 115.4(7) . . ? F27B C27 C24 112.7(8) . . ? F27F C27 C24 113.2(6) . . ? F27C C27 C24 115.3(8) . . ? F27D C27 C24 107.7(8) . . ? F27A C27 C24 109.8(6) . . ? F28F C28 F28A 13.6(19) . . ? F28F C28 F28D 108.2(10) . . ? F28A C28 F28D 115.9(12) . . ? F28F C28 F28E 108.1(11) . . ? F28A C28 F28E 94.7(14) . . ? F28D C28 F28E 107.0(8) . . ? F28F C28 F28B 119.7(14) . . ? F28A C28 F28B 106.6(10) . . ? F28D C28 F28B 97.3(9) . . ? F28E C28 F28B 12.7(13) . . ? F28F C28 F28C 96.1(13) . . ? F28A C28 F28C 104.3(9) . . ? F28D C28 F28C 12.1(12) . . ? F28E C28 F28C 112.7(9) . . ? F28B C28 F28C 104.7(8) . . ? F28F C28 C22 109.5(10) . . ? F28A C28 C22 114.5(8) . . ? F28D C28 C22 109.4(7) . . ? F28E C28 C22 114.5(6) . . ? F28B C28 C22 111.8(7) . . ? F28C C28 C22 114.1(6) . . ? F29F C29 F29B 5.3(11) . . ? F29F C29 F29C 112.0(12) . . ? F29B C29 F29C 108.1(9) . . ? F29F C29 F29A 101.9(11) . . ? F29B C29 F29A 106.7(9) . . ? F29C C29 F29A 105.6(11) . . ? F29F C29 F29E 106.8(8) . . ? F29B C29 F29E 102.5(10) . . ? F29C C29 F29E 9.2(17) . . ? F29A C29 F29E 114.6(14) . . ? F29F C29 F29D 105.2(7) . . ? F29B C29 F29D 109.6(9) . . ? F29C C29 F29D 97.1(13) . . ? F29A C29 F29D 8.5(15) . . ? F29E C29 F29D 106.0(9) . . ? F29F C29 C26 112.8(7) . . ? F29B C29 C26 112.4(6) . . ? F29C C29 C26 113.6(10) . . ? F29A C29 C26 110.0(9) . . ? F29E C29 C26 110.5(8) . . ? F29D C29 C26 114.9(7) . . ? 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 N11 S11 S12 N12 -0.4(2) . . . . ? S12 S11 N11 C10 0.4(3) . . . . ? S11 S12 N12 C10 0.3(4) . . . . ? S12 N12 C10 N11 0.0(6) . . . . ? S12 N12 C10 C11 175.2(3) . . . . ? S11 N11 C10 N12 -0.4(6) . . . . ? S11 N11 C10 C11 -175.6(3) . . . . ? N12 C10 C11 C16 -88.6(5) . . . . ? N11 C10 C11 C16 86.9(4) . . . . ? N12 C10 C11 C12 94.3(5) . . . . ? N11 C10 C11 C12 -90.3(4) . . . . ? C16 C11 C12 C13 -1.1(5) . . . . ? C10 C11 C12 C13 176.1(3) . . . . ? C16 C11 C12 C18 179.8(3) . . . . ? C10 C11 C12 C18 -3.0(5) . . . . ? C11 C12 C13 C14 -0.9(6) . . . . ? C18 C12 C13 C14 178.2(3) . . . . ? C12 C13 C14 C15 2.4(6) . . . . ? C12 C13 C14 C17 -177.0(4) . . . . ? C13 C14 C15 C16 -1.8(5) . . . . ? C17 C14 C15 C16 177.6(4) . . . . ? C12 C11 C16 C15 1.7(5) . . . . ? C10 C11 C16 C15 -175.5(3) . . . . ? C12 C11 C16 C19 -178.9(3) . . . . ? C10 C11 C16 C19 3.8(5) . . . . ? C14 C15 C16 C11 -0.3(5) . . . . ? C14 C15 C16 C19 -179.7(3) . . . . ? C13 C14 C17 F17D 117.3(11) . . . . ? C15 C14 C17 F17D -62.1(11) . . . . ? C13 C14 C17 F17B -40.5(10) . . . . ? C15 C14 C17 F17B 140.2(9) . . . . ? C13 C14 C17 F17C -172.7(8) . . . . ? C15 C14 C17 F17C 8.0(9) . . . . ? C13 C14 C17 F17E -10.3(9) . . . . ? C15 C14 C17 F17E 170.4(8) . . . . ? C13 C14 C17 F17F -121.3(10) . . . . ? C15 C14 C17 F17F 59.4(10) . . . . ? C13 C14 C17 F17A 75.6(8) . . . . ? C15 C14 C17 F17A -103.8(7) . . . . ? C13 C12 C18 F18F -88.5(7) . . . . ? C11 C12 C18 F18F 90.5(7) . . . . ? C13 C12 C18 F18A 111.1(7) . . . . ? C11 C12 C18 F18A -69.8(7) . . . . ? C13 C12 C18 F18E 32.8(7) . . . . ? C11 C12 C18 F18E -148.1(5) . . . . ? C13 C12 C18 F18D 150.8(6) . . . . ? C11 C12 C18 F18D -30.1(6) . . . . ? C13 C12 C18 F18B -11.5(8) . . . . ? C11 C12 C18 F18B 167.5(7) . . . . ? C13 C12 C18 F18C -129.7(6) . . . . ? C11 C12 C18 F18C 49.4(7) . . . . ? C11 C16 C19 F19E -46.0(7) . . . . ? C15 C16 C19 F19E 133.4(6) . . . . ? C11 C16 C19 F19C 166.7(8) . . . . ? C15 C16 C19 F19C -13.9(8) . . . . ? C11 C16 C19 F19A 34.8(6) . . . . ? C15 C16 C19 F19A -145.9(6) . . . . ? C11 C16 C19 F19F -167.9(6) . . . . ? C15 C16 C19 F19F 11.4(7) . . . . ? C11 C16 C19 F19B -77.9(6) . . . . ? C15 C16 C19 F19B 101.4(6) . . . . ? C11 C16 C19 F19D 79.2(6) . . . . ? C15 C16 C19 F19D -101.4(5) . . . . ? N22 S22 S21 N21 -0.47(19) . . . . ? S22 S21 N21 C20 -0.7(3) . . . . ? S21 S22 N22 C20 1.6(3) . . . . ? S21 N21 C20 N22 2.3(5) . . . . ? S21 N21 C20 C21 -175.2(2) . . . . ? S22 N22 C20 N21 -2.8(5) . . . . ? S22 N22 C20 C21 174.7(2) . . . . ? N21 C20 C21 C26 79.4(4) . . . . ? N22 C20 C21 C26 -98.3(4) . . . . ? N21 C20 C21 C22 -103.2(4) . . . . ? N22 C20 C21 C22 79.1(4) . . . . ? C26 C21 C22 C23 1.7(5) . . . . ? C20 C21 C22 C23 -175.8(3) . . . . ? C26 C21 C22 C28 -179.9(3) . . . . ? C20 C21 C22 C28 2.7(5) . . . . ? C21 C22 C23 C24 0.6(5) . . . . ? C28 C22 C23 C24 -177.9(3) . . . . ? C22 C23 C24 C25 -2.6(5) . . . . ? C22 C23 C24 C27 176.3(4) . . . . ? C23 C24 C25 C26 2.3(5) . . . . ? C27 C24 C25 C26 -176.6(4) . . . . ? C22 C21 C26 C25 -2.0(5) . . . . ? C20 C21 C26 C25 175.5(3) . . . . ? C22 C21 C26 C29 176.3(3) . . . . ? C20 C21 C26 C29 -6.2(5) . . . . ? C24 C25 C26 C21 0.1(5) . . . . ? C24 C25 C26 C29 -178.4(3) . . . . ? C23 C24 C27 F27E -48.1(10) . . . . ? C25 C24 C27 F27E 130.8(9) . . . . ? C23 C24 C27 F27B 171.2(9) . . . . ? C25 C24 C27 F27B -9.9(10) . . . . ? C23 C24 C27 F27F -174.0(7) . . . . ? C25 C24 C27 F27F 4.9(8) . . . . ? C23 C24 C27 F27C 46.9(10) . . . . ? C25 C24 C27 F27C -134.2(9) . . . . ? C23 C24 C27 F27D 73.3(10) . . . . ? C25 C24 C27 F27D -107.8(10) . . . . ? C23 C24 C27 F27A -69.5(7) . . . . ? C25 C24 C27 F27A 109.3(7) . . . . ? C23 C22 C28 F28F 88.9(11) . . . . ? C21 C22 C28 F28F -89.6(11) . . . . ? C23 C22 C28 F28A 102.5(11) . . . . ? C21 C22 C28 F28A -76.0(11) . . . . ? C23 C22 C28 F28D -29.5(7) . . . . ? C21 C22 C28 F28D 152.0(7) . . . . ? C23 C22 C28 F28E -149.6(8) . . . . ? C21 C22 C28 F28E 31.9(9) . . . . ? C23 C22 C28 F28B -136.1(8) . . . . ? C21 C22 C28 F28B 45.4(8) . . . . ? C23 C22 C28 F28C -17.6(9) . . . . ? C21 C22 C28 F28C 164.0(8) . . . . ? C21 C26 C29 F29F 160.7(7) . . . . ? C25 C26 C29 F29F -20.9(8) . . . . ? C21 C26 C29 F29B 166.4(7) . . . . ? C25 C26 C29 F29B -15.2(8) . . . . ? C21 C26 C29 F29C -70.4(11) . . . . ? C25 C26 C29 F29C 108.0(10) . . . . ? C21 C26 C29 F29A 47.7(10) . . . . ? C25 C26 C29 F29A -133.9(9) . . . . ? C21 C26 C29 F29E -79.8(9) . . . . ? C25 C26 C29 F29E 98.6(9) . . . . ? C21 C26 C29 F29D 40.1(8) . . . . ? C25 C26 C29 F29D -141.5(7) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.311 _refine_diff_density_min -0.451 _refine_diff_density_rms 0.064