# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2004 data_global _journal_name_full Org.Biomol.Chem. #=============================================================================== # 1. SUBMISSION DETAILS _journal_coden_Cambridge 0177 #============================================================================== # 0. AUDIT DETAILS _audit_creation_date '2002-01-08 09:52:00' _audit_creation_method 'PLATON option' _audit_update_record ; ? ; _publ_contact_author_name # Name of author for correspondence 'Prof Ben Feringa' _publ_contact_author_address # Address of author for correspondence ; Organic and Molecular Inorganic Chemistry University of Groningen Nijenborgh 4 Groningen 9747 AG NETHERLANDS ; _publ_contact_author_email FERINGA@CHEM.RUG.NL _publ_section_title ; Exploring the boundaries of a light-driven molecular motor design: new sterically overcrowded alkenes with preferred direction of rotation ; # Insert blank lines between references _publ_section_references ; Altomare, A., Burla, M.C., Camalli, M., Cascarano, G.L., (1999) J. Appl. Cryst. 32, 115-119. Bruker, (2000). SMART, SAINT, SADABS, XPREP and SHELXTL/NT. Software Reference Manual Bruker AXS Inc. Madison, Wisconsin, USA. International Tables for Crystallography (1983). Vol. A. Space-group symmetry, edited by T. Hahn. Dordrecht: Reidel. (Present distributor Kluwer Academic Publishers, Dordrecht). International Tables for Crystallography (1992). Vol. C. Edited by A.J.C Wilson, Kluwer Academic Publishers, Dordrecht, The Netherlands. Le Page, Y. (1987). J. Appl. Cryst. 20, 264-269. Le Page, Y. (1988). J. Appl. Cryst. 21, 983-984. Meetsma, A. (2001). Extended version of the program PLUTO. Groningen University, The Netherlands. (unpublished). Sheldrick, G.M. SHELXL97. Program for Crystal Structure Refinement. University of Gottingen, Germany, 1997. Sheldrick, G.M. SADABS. Version 2. Multi-Scan Absorption Correction Program. University of Gottingen, Germany, 2001 Spek, A.L. (1987). Acta Cryst. C43, 1233-1235. Spek, A.L. (1988). J. Appl. Cryst. 21, 578-579. Spek, A.L. (1990). Acta Cryst. A46, C-34. ; _publ_section_figure_captions ; Fig. 1. Chemical structural diagram (scheme 1) of the title compound Fig. 2. Perspective PLUTO drawing of the molecule illustrating the configuration and the adopted numbering scheme. Fig. 3. Molecular packing viewed down unit cell axes. Fig. 4. Perspective ORTEP drawing of the title compound. Displacement ellipsoids for non-H are represented at the 50% probability level. The H-atoms are drawn with an arbitrary radius. ; loop_ _publ_author_name 'Ben Feringa' 'Harmen de Jong' 'Matthijs K.J. ter Wiel' 'Richard van Delden' #=============================================================================== data_c27h20s2 _database_code_depnum_ccdc_archive 'CCDC 231703' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C27 H20 S2' _chemical_formula_structural ? # Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)' _chemical_formula_sum 'C27 H20 S2' _chemical_formula_weight 408.59 _chemical_compound_source 'see text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source S S 0.1246 0.1234 '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' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 21/n' loop_ _symmetry_equiv_pos_as_xyz x,y,z 1/2-x,1/2+y,1/2-z -x,-y,-z 1/2+x,1/2-y,1/2+z _cell_length_a 8.827(2) _cell_length_b 21.647(4) _cell_length_c 11.075(2) _cell_angle_alpha 90 _cell_angle_beta 100.493(3) _cell_angle_gamma 90 _cell_volume 2080.8(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(1) _cell_measurement_reflns_used 3334 _cell_measurement_theta_min 2.53 _cell_measurement_theta_max 21.79 _cell_special_details ; The final unit cell was obtained from the xyz centroids of 3334 reflections after integration using the SAINT software package (Bruker, 2000). ; _exptl_crystal_description platelet _exptl_crystal_colour colorless _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.08 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.304 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 856 _exptl_absorpt_coefficient_mu 0.267 _exptl_absorpt_correction_type Multi-Scan _exptl_absorpt_process_details '(SADABS, Sheldrick, Bruker, 2000))' _exptl_absorpt_correction_T_min 0.8940 _exptl_absorpt_correction_T_max 0.9790 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine focus sealed Siemens Mo tube ' _diffrn_radiation_monochromator 'parallel mounted graphite' _diffrn_radiation_detector ; CCD area-detector ; _diffrn_measurement_device_type ; Bruker Smart Apex ; _diffrn_measurement_method 'phi and omega scans' _diffrn_special_details ? _diffrn_detector_area_resol_mean '4096x4096 / 62x62 (binned 512)' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? # number of measured reflections (redundant set) _diffrn_reflns_number 14823 _diffrn_reflns_av_R_equivalents 0.0379 _diffrn_reflns_av_sigmaI/netI 0.0446 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.53 _diffrn_reflns_theta_max 25.02 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_reduction_process ; Intensity data were corrected for Lorentz and polarization effects, decay and absorption and reduced to F~o~^2^ using SAINT (Bruker, 2000) and SADABS (Sheldrick, 2001) ; # number of unique reflections _reflns_number_total 3673 _reflns_number_gt 2408 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART, Bruker Version 5.624, 2001' _computing_cell_refinement 'SAINT, Bruker Version 6.02A, 2000' _computing_data_reduction 'XPREP, Bruker Version 5.1/NT, 2000' _computing_structure_solution ; SIR-97 (Altomare et al., 1997) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; PLUTO (Meetsma, 2001) PLATON (Spek, 1994) ; _computing_publication_material ; PLATON (Spek, 1990) SHELXL (Sheldrick, 1997) ; #=============================================================================== # 8. REFINEMENT DATA _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. ; _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^)+(0.0598P)^2^+0.4521P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary direct _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 3673 _refine_ls_number_parameters 331 _refine_ls_number_restraints 0 _refine_ls_number_constraints ? _refine_ls_R_factor_all 0.0834 _refine_ls_R_factor_gt 0.0498 _refine_ls_wR_factor_ref 0.1342 _refine_ls_wR_factor_gt 0.1179 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.022 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.342 _refine_diff_density_min -0.302 _refine_diff_density_rms 0.037 _vrn_publ_code_void_volume 0.0 _vrn_publ_code_frame_time 20.0 _vrn_publ_code_meas_time 13.3 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags S1 S Uani -0.07387(11) 0.26828(5) -0.04988(7) 1.000 0.0981(4) . . S2 S Uani 0.08229(9) 0.35570(4) 0.56883(6) 1.000 0.0832(3) . . C1 C Uani 0.0182(3) 0.33838(14) -0.0034(2) 1.000 0.0690(10) . . C2 C Uani 0.0279(4) 0.3816(2) -0.0955(3) 1.000 0.0887(14) . . C3 C Uani 0.0987(5) 0.4355(2) -0.0668(3) 1.000 0.0926(16) . . C4 C Uani 0.1717(4) 0.44998(15) 0.0551(3) 1.000 0.0763(12) . . C5 C Uani 0.2578(5) 0.50398(19) 0.0842(5) 1.000 0.0998(19) . . C6 C Uani 0.3316(5) 0.51568(18) 0.2001(5) 1.000 0.0977(18) . . C7 C Uani 0.3224(4) 0.47323(17) 0.2943(4) 1.000 0.0827(16) . . C8 C Uani 0.2386(3) 0.42051(15) 0.2700(3) 1.000 0.0651(11) . . C9 C Uani 0.1605(3) 0.40705(12) 0.1499(2) 1.000 0.0592(9) . . C10 C Uani 0.0759(3) 0.35128(13) 0.1191(2) 1.000 0.0564(9) . . C11 C Uani 0.0613(3) 0.30195(11) 0.2093(2) 1.000 0.0509(8) . . C12 C Uani 0.1211(3) 0.24143(14) 0.1709(3) 1.000 0.0605(10) . . C13 C Uani 0.0067(4) 0.21327(16) 0.0646(3) 1.000 0.0872(12) . . C14 C Uani 0.0730(5) 0.1597(2) 0.0078(4) 1.000 0.1394(19) . . C15 C Uani -0.0046(3) 0.30976(11) 0.3090(2) 1.000 0.0515(8) . . C16 C Uani -0.0097(3) 0.26206(13) 0.4038(3) 1.000 0.0606(10) . . C17 C Uani -0.0596(3) 0.20202(16) 0.3785(4) 1.000 0.0754(11) . . C18 C Uani -0.0560(4) 0.1593(2) 0.4730(6) 1.000 0.0979(18) . . C19 C Uani -0.0052(5) 0.1766(3) 0.5921(5) 1.000 0.110(2) . . C20 C Uani 0.0388(4) 0.2358(3) 0.6206(4) 1.000 0.0912(18) . . C21 C Uani 0.0337(3) 0.27903(14) 0.5278(3) 1.000 0.0692(10) . . C22 C Uani -0.0502(3) 0.39281(13) 0.4542(2) 1.000 0.0616(10) . . C23 C Uani -0.1252(4) 0.44605(15) 0.4818(3) 1.000 0.0760(12) . . C24 C Uani -0.2277(4) 0.47493(16) 0.3924(4) 1.000 0.0811(14) . . C25 C Uani -0.2589(4) 0.45126(15) 0.2751(3) 1.000 0.0728(11) . . C26 C Uani -0.1859(3) 0.39850(13) 0.2468(3) 1.000 0.0610(10) . . C27 C Uani -0.0783(3) 0.36848(12) 0.3348(2) 1.000 0.0539(8) . . H2 H Uiso -0.023(4) 0.3676(15) -0.187(3) 1.000 0.112(11) . . H3 H Uiso 0.105(4) 0.4640(16) -0.123(3) 1.000 0.112(13) . . H5 H Uiso 0.258(4) 0.5342(17) 0.019(4) 1.000 0.123(13) . . H6 H Uiso 0.382(4) 0.5526(16) 0.215(3) 1.000 0.099(12) . . H7 H Uiso 0.373(3) 0.4777(13) 0.372(3) 1.000 0.074(10) . . H8 H Uiso 0.233(3) 0.3920(10) 0.329(2) 1.000 0.045(7) . . H12 H Uiso 0.219(3) 0.2492(11) 0.150(2) 1.000 0.067(8) . . H12' H Uiso 0.138(3) 0.2104(12) 0.238(2) 1.000 0.072(8) . . H13 H Uiso -0.092(5) 0.1945(17) 0.099(4) 1.000 0.143(15) . . H14 H Uiso 0.16414 0.17253 -0.02117 1.000 0.2089 . . H14' H Uiso -0.00126 0.14441 -0.05987 1.000 0.2089 . . H14" H Uiso 0.09879 0.12758 0.06782 1.000 0.2089 . . H17 H Uiso -0.096(3) 0.1899(10) 0.300(2) 1.000 0.047(7) . . H18 H Uiso -0.088(3) 0.1212(15) 0.447(3) 1.000 0.078(10) . . H19 H Uiso -0.012(4) 0.1489(17) 0.657(4) 1.000 0.124(13) . . H20 H Uiso 0.066(4) 0.2501(15) 0.712(3) 1.000 0.110(12) . . H23 H Uiso -0.101(3) 0.4621(12) 0.565(3) 1.000 0.083(9) . . H24 H Uiso -0.278(3) 0.5104(12) 0.409(2) 1.000 0.066(8) . . H25 H Uiso -0.337(4) 0.4716(15) 0.218(3) 1.000 0.102(11) . . H26 H Uiso -0.208(3) 0.3812(11) 0.167(2) 1.000 0.064(8) . . 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 0.0896(6) 0.1333(8) 0.0607(5) -0.0188(5) -0.0147(4) 0.0014(5) S2 0.0773(5) 0.1227(7) 0.0479(4) -0.0074(4) 0.0071(3) 0.0019(5) C1 0.0671(17) 0.097(2) 0.0434(15) 0.0077(15) 0.0114(12) 0.0224(15) C2 0.088(2) 0.123(3) 0.057(2) 0.018(2) 0.0186(17) 0.030(2) C3 0.100(3) 0.115(3) 0.069(2) 0.043(2) 0.032(2) 0.039(2) C4 0.076(2) 0.072(2) 0.089(2) 0.0224(18) 0.0369(18) 0.0209(17) C5 0.108(3) 0.082(3) 0.121(4) 0.031(3) 0.052(3) 0.020(2) C6 0.096(3) 0.064(2) 0.146(4) 0.004(3) 0.056(3) -0.002(2) C7 0.072(2) 0.085(3) 0.097(3) -0.015(2) 0.031(2) -0.0036(18) C8 0.0592(17) 0.074(2) 0.0675(19) 0.0002(17) 0.0258(14) -0.0036(15) C9 0.0561(15) 0.0692(18) 0.0579(16) 0.0086(14) 0.0256(13) 0.0141(14) C10 0.0492(14) 0.0766(18) 0.0454(14) 0.0067(13) 0.0139(11) 0.0119(13) C11 0.0473(13) 0.0636(16) 0.0403(13) -0.0029(12) 0.0039(10) 0.0009(12) C12 0.0521(16) 0.0735(19) 0.0555(16) -0.0078(15) 0.0091(13) -0.0003(14) C13 0.084(2) 0.095(2) 0.077(2) -0.0250(18) -0.0004(18) 0.0015(19) C14 0.128(3) 0.139(3) 0.138(4) -0.075(3) -0.011(3) 0.033(3) C15 0.0465(13) 0.0617(16) 0.0453(14) 0.0021(12) 0.0060(11) -0.0005(12) C16 0.0492(14) 0.0726(19) 0.0627(17) 0.0130(14) 0.0174(12) 0.0051(13) C17 0.0632(19) 0.079(2) 0.088(2) 0.012(2) 0.0244(18) -0.0028(16) C18 0.072(2) 0.077(3) 0.154(4) 0.036(3) 0.045(2) 0.005(2) C19 0.076(2) 0.148(5) 0.116(4) 0.075(4) 0.043(2) 0.029(3) C20 0.069(2) 0.134(4) 0.076(3) 0.038(3) 0.0272(18) 0.023(2) C21 0.0554(16) 0.102(2) 0.0544(16) 0.0211(16) 0.0212(13) 0.0130(15) C22 0.0560(16) 0.0746(19) 0.0575(17) -0.0074(14) 0.0189(13) -0.0080(14) C23 0.074(2) 0.083(2) 0.077(2) -0.0240(19) 0.0300(17) -0.0136(18) C24 0.079(2) 0.063(2) 0.110(3) -0.008(2) 0.040(2) 0.0018(17) C25 0.0631(19) 0.073(2) 0.087(2) 0.0079(18) 0.0261(17) 0.0046(16) C26 0.0551(16) 0.0690(19) 0.0609(18) 0.0016(15) 0.0161(14) 0.0020(14) C27 0.0512(14) 0.0640(16) 0.0496(14) 0.0012(12) 0.0175(11) -0.0040(12) #=============================================================================== # 10. MOLECULAR GEOMETRY _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All esds are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C1 1.754(3) . . yes S1 C13 1.790(4) . . yes S2 C21 1.753(3) . . yes S2 C22 1.756(3) . . yes C1 C2 1.398(5) . . no C1 C10 1.388(3) . . no C2 C3 1.334(6) . . no C3 C4 1.421(5) . . no C4 C5 1.400(5) . . no C4 C9 1.419(4) . . no C5 C6 1.353(8) . . no C6 C7 1.404(6) . . no C7 C8 1.360(5) . . no C8 C9 1.413(4) . . no C9 C10 1.428(4) . . no C10 C11 1.484(3) . . no C11 C12 1.503(4) . . no C11 C15 1.349(3) . . no C12 C13 1.531(5) . . no C13 C14 1.489(6) . . no C15 C16 1.479(4) . . no C15 C27 1.479(4) . . no C16 C17 1.384(4) . . no C16 C21 1.406(5) . . no C17 C18 1.393(7) . . no C18 C19 1.366(8) . . no C19 C20 1.359(9) . . no C20 C21 1.385(6) . . no C22 C23 1.391(4) . . no C22 C27 1.403(3) . . no C23 C24 1.365(5) . . no C24 C25 1.377(5) . . no C25 C26 1.375(4) . . no C26 C27 1.392(4) . . no C2 H2 1.07(3) . . no C3 H3 0.89(3) . . no C5 H5 0.97(4) . . no C6 H6 0.91(4) . . no C7 H7 0.90(3) . . no C8 H8 0.91(2) . . no C12 H12 0.95(3) . . no C12 H12' 0.99(2) . . no C13 H13 1.09(4) . . no C14 H14 0.9598 . . no C14 H14' 0.9602 . . no C14 H14" 0.9602 . . no C17 H17 0.91(2) . . no C18 H18 0.90(3) . . no C19 H19 0.95(4) . . no C20 H20 1.04(3) . . no C23 H23 0.97(3) . . no C24 H24 0.92(3) . . no C25 H25 0.95(3) . . no C26 H26 0.95(2) . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 S1 C13 105.35(14) . . . yes C21 S2 C22 98.42(14) . . . yes S1 C1 C2 116.8(2) . . . yes S1 C1 C10 121.9(2) . . . yes C2 C1 C10 121.2(3) . . . no C1 C2 C3 120.0(3) . . . no C2 C3 C4 122.1(3) . . . no C3 C4 C5 122.4(4) . . . no C3 C4 C9 118.5(3) . . . no C5 C4 C9 119.0(3) . . . no C4 C5 C6 121.5(4) . . . no C5 C6 C7 120.0(4) . . . no C6 C7 C8 120.4(4) . . . no C7 C8 C9 120.9(3) . . . no C4 C9 C8 118.3(3) . . . no C4 C9 C10 118.7(2) . . . no C8 C9 C10 122.9(2) . . . no C1 C10 C9 119.1(2) . . . no C1 C10 C11 116.9(2) . . . no C9 C10 C11 123.6(2) . . . no C10 C11 C12 111.0(2) . . . no C10 C11 C15 124.3(2) . . . no C12 C11 C15 124.5(2) . . . no C11 C12 C13 110.4(2) . . . no S1 C13 C12 113.7(2) . . . yes S1 C13 C14 110.8(3) . . . yes C12 C13 C14 112.3(3) . . . no C11 C15 C16 124.5(2) . . . no C11 C15 C27 122.4(2) . . . no C16 C15 C27 113.0(2) . . . no C15 C16 C17 124.2(3) . . . no C15 C16 C21 118.2(2) . . . no C17 C16 C21 117.6(3) . . . no C16 C17 C18 120.6(4) . . . no C17 C18 C19 120.1(4) . . . no C18 C19 C20 120.8(5) . . . no C19 C20 C21 119.7(4) . . . no S2 C21 C16 120.7(2) . . . yes S2 C21 C20 118.3(3) . . . yes C16 C21 C20 121.0(3) . . . no S2 C22 C23 120.1(2) . . . yes S2 C22 C27 119.3(2) . . . yes C23 C22 C27 120.6(2) . . . no C22 C23 C24 120.0(3) . . . no C23 C24 C25 120.4(3) . . . no C24 C25 C26 120.2(3) . . . no C25 C26 C27 121.1(3) . . . no C15 C27 C22 119.7(2) . . . no C15 C27 C26 122.3(2) . . . no C22 C27 C26 117.8(2) . . . no C1 C2 H2 115.4(18) . . . no C3 C2 H2 124.6(18) . . . no C2 C3 H3 122(2) . . . no C4 C3 H3 116(2) . . . no C4 C5 H5 118(2) . . . no C6 C5 H5 121(2) . . . no C5 C6 H6 118(2) . . . no C7 C6 H6 122(2) . . . no C6 C7 H7 123.7(18) . . . no C8 C7 H7 115.9(18) . . . no C7 C8 H8 121.8(15) . . . no C9 C8 H8 117.2(15) . . . no C11 C12 H12 107.3(15) . . . no C11 C12 H12' 113.0(15) . . . no C13 C12 H12 112.7(14) . . . no C13 C12 H12' 107.1(15) . . . no H12 C12 H12' 106(2) . . . no S1 C13 H13 105(2) . . . no C12 C13 H13 110(2) . . . no C14 C13 H13 105(2) . . . no C13 C14 H14 109.49 . . . no C13 C14 H14' 109.47 . . . no C13 C14 H14" 109.47 . . . no H14 C14 H14' 109.48 . . . no H14 C14 H14" 109.48 . . . no H14' C14 H14" 109.44 . . . no C16 C17 H17 120.6(14) . . . no C18 C17 H17 118.9(14) . . . no C17 C18 H18 114(2) . . . no C19 C18 H18 126(2) . . . no C18 C19 H19 120(2) . . . no C20 C19 H19 118(2) . . . no C19 C20 H20 120.7(18) . . . no C21 C20 H20 119.3(19) . . . no C22 C23 H23 118.3(16) . . . no C24 C23 H23 121.8(16) . . . no C23 C24 H24 121.1(14) . . . no C25 C24 H24 118.5(14) . . . no C24 C25 H25 117(2) . . . no C26 C25 H25 123(2) . . . no C25 C26 H26 121.0(15) . . . no C27 C26 H26 117.9(15) . . . no 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 C13 S1 C1 C2 154.0(3) . . . . no C13 S1 C1 C10 -27.4(3) . . . . no C1 S1 C13 C12 3.4(3) . . . . no C1 S1 C13 C14 -124.2(3) . . . . no C22 S2 C21 C16 35.9(3) . . . . no C22 S2 C21 C20 -143.9(3) . . . . no C21 S2 C22 C23 140.9(3) . . . . no C21 S2 C22 C27 -39.6(2) . . . . no C10 C1 C2 C3 2.5(5) . . . . no S1 C1 C10 C9 175.0(2) . . . . no S1 C1 C2 C3 -178.9(3) . . . . no C2 C1 C10 C9 -6.5(4) . . . . no C2 C1 C10 C11 -179.3(3) . . . . no S1 C1 C10 C11 2.2(4) . . . . no C1 C2 C3 C4 2.8(6) . . . . no C2 C3 C4 C9 -3.8(6) . . . . no C2 C3 C4 C5 174.2(4) . . . . no C3 C4 C5 C6 -177.3(4) . . . . no C3 C4 C9 C8 177.4(3) . . . . no C3 C4 C9 C10 -0.3(5) . . . . no C9 C4 C5 C6 0.7(6) . . . . no C5 C4 C9 C10 -178.4(3) . . . . no C5 C4 C9 C8 -0.7(5) . . . . no C4 C5 C6 C7 -0.2(7) . . . . no C5 C6 C7 C8 -0.5(6) . . . . no C6 C7 C8 C9 0.6(5) . . . . no C7 C8 C9 C4 0.0(4) . . . . no C7 C8 C9 C10 177.6(3) . . . . no C4 C9 C10 C11 177.6(3) . . . . no C8 C9 C10 C1 -172.3(3) . . . . no C8 C9 C10 C11 0.0(4) . . . . no C4 C9 C10 C1 5.3(4) . . . . no C1 C10 C11 C12 50.6(3) . . . . no C9 C10 C11 C12 -121.9(3) . . . . no C9 C10 C11 C15 61.4(4) . . . . no C1 C10 C11 C15 -126.1(3) . . . . no C15 C11 C12 C13 101.9(3) . . . . no C10 C11 C15 C16 -175.5(2) . . . . no C10 C11 C15 C27 3.7(4) . . . . no C12 C11 C15 C16 8.3(4) . . . . no C12 C11 C15 C27 -172.5(2) . . . . no C10 C11 C12 C13 -74.8(3) . . . . no C11 C12 C13 S1 42.4(3) . . . . no C11 C12 C13 C14 169.2(3) . . . . no C11 C15 C16 C21 131.7(3) . . . . no C27 C15 C16 C17 130.2(3) . . . . no C27 C15 C16 C21 -47.6(3) . . . . no C11 C15 C27 C22 -135.6(3) . . . . no C11 C15 C27 C26 49.9(4) . . . . no C16 C15 C27 C22 43.6(3) . . . . no C16 C15 C27 C26 -130.8(3) . . . . no C11 C15 C16 C17 -50.6(4) . . . . no C21 C16 C17 C18 -4.4(4) . . . . no C15 C16 C21 S2 3.4(4) . . . . no C15 C16 C21 C20 -176.7(3) . . . . no C17 C16 C21 S2 -174.4(2) . . . . no C17 C16 C21 C20 5.4(4) . . . . no C15 C16 C17 C18 177.9(3) . . . . no C16 C17 C18 C19 1.0(5) . . . . no C17 C18 C19 C20 1.7(6) . . . . no C18 C19 C20 C21 -0.7(6) . . . . no C19 C20 C21 C16 -2.9(5) . . . . no C19 C20 C21 S2 176.9(3) . . . . no S2 C22 C23 C24 179.8(3) . . . . no S2 C22 C27 C15 4.2(4) . . . . no S2 C22 C27 C26 179.0(2) . . . . no C27 C22 C23 C24 0.3(5) . . . . no C23 C22 C27 C26 -1.6(4) . . . . no C23 C22 C27 C15 -176.3(3) . . . . no C22 C23 C24 C25 0.8(5) . . . . no C23 C24 C25 C26 -0.5(5) . . . . no C24 C25 C26 C27 -0.8(5) . . . . no C25 C26 C27 C15 176.4(3) . . . . no C25 C26 C27 C22 1.8(4) . . . . no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag S1 H20 3.13(3) . 1_554 no S1 H12' 3.17(2) . 4_454 no S2 H2 3.03(3) . 1_556 no S2 H13 3.03(4) . 4_555 no C2 C5 3.553(6) . 3_565 no C3 C5 3.382(6) . 3_565 no C3 C4 3.460(6) . 3_565 no C4 C3 3.460(6) . 3_565 no C5 C2 3.553(6) . 3_565 no C5 C3 3.382(6) . 3_565 no C8 C15 3.299(4) . . no C8 C27 3.216(4) . . no C8 C22 3.594(4) . . no C9 C26 3.425(4) . . no C9 C27 3.302(4) . . no C10 C26 3.094(4) . . no C12 C17 3.145(5) . . no C14 C23 3.564(6) . 4_554 no C15 C8 3.299(4) . . no C17 C12 3.145(5) . . no C19 C26 3.430(6) . 4_555 no C22 C8 3.594(4) . . no C23 C14 3.564(6) . 4_455 no C23 C23 3.190(5) . 3_566 no C26 C10 3.094(4) . . no C26 C9 3.425(4) . . no C26 C19 3.430(6) . 4_454 no C27 C8 3.216(4) . . no C27 C9 3.302(4) . . no C1 H12 2.94(2) . . no C3 H18 3.00(3) . 4_554 no C4 H18 3.04(3) . 4_554 no C6 H25 3.05(4) . 1_655 no C7 H23 3.05(3) . 3_566 no C8 H14' 3.0368 . 4_555 no C10 H26 2.73(3) . . no C11 H8 2.67(2) . . no C11 H17 3.05(2) . . no C11 H26 2.90(3) . . no C12 H17 2.82(3) . . no C13 H17 2.96(2) . . no C15 H8 2.73(2) . . no C16 H12' 2.68(2) . . no C17 H12' 2.55(3) . . no C17 H13 3.06(4) . . no C19 H26 2.89(3) . 4_555 no C19 H12 3.08(3) . 4_455 no C20 H12 2.92(3) . 4_455 no C22 H8 3.07(3) . . no C22 H14 2.9468 . 4_455 no C23 H23 2.93(3) . 3_566 no C25 H3 2.98(3) . 3_565 no C26 H19 3.05(4) . 4_454 no C27 H8 2.81(3) . . no H2 S2 3.03(3) . 1_554 no H3 H5 2.42(5) . . no H3 C25 2.98(3) . 3_565 no H5 H3 2.42(5) . . no H8 C11 2.67(2) . . no H8 C15 2.73(2) . . no H8 C22 3.07(3) . . no H8 C27 2.81(3) . . no H8 H14' 2.5665 . 4_555 no H12 C1 2.94(2) . . no H12 H14 2.4997 . . no H12 C19 3.08(3) . 4_554 no H12 C20 2.92(3) . 4_554 no H12' C16 2.68(2) . . no H12' C17 2.55(3) . . no H12' H14" 2.5785 . . no H12' H17 2.33(4) . . no H12' S1 3.17(2) . 4_555 no H13 C17 3.06(4) . . no H13 H17 2.23(5) . . no H13 S2 3.03(4) . 4_454 no H14 H12 2.4997 . . no H14 C22 2.9468 . 4_554 no H14' C8 3.0368 . 4_454 no H14' H8 2.5665 . 4_454 no H14" H12' 2.5785 . . no H17 C11 3.05(2) . . no H17 C12 2.82(3) . . no H17 C13 2.96(2) . . no H17 H12' 2.33(4) . . no H17 H13 2.23(5) . . no H18 C3 3.00(3) . 4_455 no H18 C4 3.04(3) . 4_455 no H19 C26 3.05(4) . 4_555 no H20 S1 3.13(3) . 1_556 no H23 C7 3.05(3) . 3_566 no H23 C23 2.93(3) . 3_566 no H25 C6 3.05(4) . 1_455 no H26 C10 2.73(3) . . no H26 C11 2.90(3) . . no H26 C19 2.89(3) . 4_454 no # End of Crystallographic Information File