Supplementary Material for Organic & Biomolecular Chemistry This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full Org.Biomol.Chem. # SUBMISSION DETAILS _journal_coden_Cambridge 0177 _audit_creation_method 'SHELXL and manual editing' _publ_contact_author_name 'Prof John Wallis' _publ_contact_author_address ; Chemistry and Physics The Nottingham Trent University Clifton Lane Nottingham NG11 8NS UNITED KINGDOM ; _publ_contact_author_email john.wallis@ntu.ac.uk _publ_contact_author_fax 0115-948-6636 _publ_contact_author_phone 0115-848-3149 _publ_section_title ; Synthetic Strategies to Chiral Organosulfur Donors Related to Bis(ethylenedithio)tetrathiafulvalene. ; loop_ _publ_author_name _publ_author_address 'Jon-Paul Griffiths' ; School of Biomedical and Natural Sciences Nottingham Trent University Clifton Lane Nottingham UK NG11 8NS ; 'Nie Hui.' ; School of Biomedical and Natural Sciences Nottingham Trent University Clifton Lane Nottingham UK NG11 8NS ; 'R. James Brown' ; The Royal Institution 21 Albemarle Steet London UK W1S 4BS ; 'Peter Day' ; The Royal Institution 21 Albemarle Steet London UK W1S 4BS ; 'John D. Wallis' ; School of Biomedical and Natural Sciences Nottingham Trent University Clifton Lane Nottingham UK NG11 8NS ; # TEXT _publ_section_references ; Blessing, R.H. (1995). Acta Cryst., A51, 33-38. Hooft, R. (1998). Data Collection Software, Nonius B.V., Delft, The Netherlands. Johnson, C.K., Burnett, M.N. (1996). ORTEPIII Report ORNL-6895, Oak Ridge National Laboratory, Tennessee, USA Otwinowski, M., Minor W. (1997). Methods in Enzymology 276: macromolecular crystallography A, ed. Carter, C.W. Jr, Sweet, R.M., Academic Press, 307-326. Sheldrick, G.M. (1990). Acta Cryst. A46, 467-473. Sheldrick, G.M. (1997). SHELXL-97 Program for the Refinement of Crystal Structures, University of Gottingen, Germany. ; _publ_section_exptl_refinement ; The structures were solved using direct methods and refined with the full-matrix least-squares technique. All non-hydrogen atoms were refined with anisotropic displacement parameters, all hydrogen atoms were located in diffence fourier maps and their positions and isotropic displacement parameters refined unless otherwise stated. ; data_compound40 _database_code_depnum_ccdc_archive 'CCDC 230195' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (1R,5S,5S)-Spiro[6,6-dimethyl-bicyclo[3.1.1]heptane]-2,5- [5,6-dihydro-[1,3]dithiolo[4,5-b][1,4]dithiine-2-thione] ; _chemical_name_common ; (1R,5S,5S)-Spiro(6,6-dimethyl-bicyclo(3.1.1)heptane)-2,5-(5,6- dihydro-(1,3)dithiolo(4,5-b)(1,4)dithiine-2-thione) ; _chemical_melting_point 372-373 _chemical_formula_moiety ? _chemical_formula_sum 'C13 H16 S5' _chemical_formula_weight 332.56 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 6.3217(2) _cell_length_b 13.4551(4) _cell_length_c 17.5120(5) _cell_angle_alpha 90.00 _cell_angle_beta 93.0600(16) _cell_angle_gamma 90.00 _cell_volume 1487.43(8) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 9387 _cell_measurement_theta_min 2.81 _cell_measurement_theta_max 27.48 _exptl_crystal_description slab _exptl_crystal_colour yellow _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.485 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 696 _exptl_absorpt_coefficient_mu 0.758 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.832 _exptl_absorpt_correction_T_max 0.868 _exptl_absorpt_process_details ; Using multiple and symmetry-related data measurements via the program SORTAV See R. H. Blessing, Acta Cryst. (1995), A51, 33-38 ; _exptl_special_details ; PLEASE NOTE cell_measurement_ fields are not relevant to area detector data, the entire data set is used to refine the cell, which is indexed from all observed reflections in a 10 degree phi range. ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enraf Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Enraf Nonius KappaCCD area detector' _diffrn_measurement_method 'Phi and Omega scans to fill Ewald sphere' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19537 _diffrn_reflns_av_R_equivalents 0.0612 _diffrn_reflns_av_sigmaI/netI 0.0857 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.03 _diffrn_reflns_theta_max 27.51 _reflns_number_total 6771 _reflns_number_gt 5327 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; 'DENZO (Otwinowski and Minor, 1997)' 'COLLECT (Hooft, 1998)' ; _computing_cell_refinement ; 'DENZO (Otwinowski and Minor, 1997)' 'COLLECT (Hooft, 1998)' ; _computing_data_reduction ; 'DENZO (Otwinowski and Minor, 1997)' 'COLLECT (Hooft, 1998)' ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP3 (Johnson and Burnett, 1996)' _computing_publication_material 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _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(8) _refine_ls_number_reflns 6771 _refine_ls_number_parameters 453 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0682 _refine_ls_R_factor_gt 0.0422 _refine_ls_wR_factor_ref 0.1131 _refine_ls_wR_factor_gt 0.0989 _refine_ls_goodness_of_fit_ref 0.820 _refine_ls_restrained_S_all 0.820 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 _chemical_absolute_configuration syn 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 0.01229(16) 0.07319(8) 0.39818(6) 0.0265(2) Uani 1 1 d . . . S12 S 0.26348(16) 0.09436(7) 0.26074(5) 0.0235(2) Uani 1 1 d . . . S13 S -0.13024(15) -0.01323(8) 0.24696(6) 0.0239(2) Uani 1 1 d . . . S14 S 0.39759(15) 0.05029(8) 0.10607(6) 0.0241(2) Uani 1 1 d . . . S15 S -0.09108(15) -0.07742(8) 0.08615(6) 0.0239(2) Uani 1 1 d . . . C11 C 0.0451(6) 0.0536(3) 0.3067(2) 0.0228(8) Uani 1 1 d . . . C12 C 0.2043(6) 0.0381(3) 0.1727(2) 0.0216(8) Uani 1 1 d . . . C13 C 0.0190(6) -0.0118(3) 0.1652(2) 0.0221(8) Uani 1 1 d . . . C14 C 0.2500(7) 0.0077(3) 0.0210(2) 0.0221(8) Uani 1 1 d . . . C15 C 0.1433(6) -0.0942(3) 0.0279(2) 0.0200(8) Uani 1 1 d . . . C16 C 0.2947(7) -0.1754(3) 0.0633(2) 0.0229(8) Uani 1 1 d . . . C17 C 0.3042(7) -0.2741(3) 0.0177(3) 0.0276(9) Uani 1 1 d . . . C18 C 0.1697(7) -0.2725(3) -0.0574(3) 0.0269(9) Uani 1 1 d . . . C19 C -0.0520(6) -0.2327(3) -0.0402(3) 0.0247(9) Uani 1 1 d . . . C110 C 0.0414(6) -0.1274(3) -0.0496(2) 0.0212(8) Uani 1 1 d . . . C111 C 0.2033(6) -0.1757(3) -0.1038(2) 0.0243(9) Uani 1 1 d . . . C112 C 0.4284(7) -0.1383(4) -0.1094(3) 0.0284(9) Uani 1 1 d . . . C113 C 0.1057(8) -0.1838(4) -0.1850(3) 0.0358(11) Uani 1 1 d . . . H14A H 0.358(7) 0.005(3) -0.019(2) 0.019(10) Uiso 1 1 d . . . H14B H 0.163(9) 0.052(4) 0.008(3) 0.043(15) Uiso 1 1 d . . . H16A H 0.252(7) -0.193(3) 0.116(3) 0.022(11) Uiso 1 1 d . . . H16B H 0.437(8) -0.147(3) 0.069(3) 0.029(12) Uiso 1 1 d . . . H17A H 0.260(7) -0.335(4) 0.050(3) 0.026(12) Uiso 1 1 d . . . H17B H 0.438(8) -0.281(4) 0.005(3) 0.034(13) Uiso 1 1 d . . . H18 H 0.171(7) -0.337(3) -0.083(2) 0.017(10) Uiso 1 1 d . . . H19A H -0.164(7) -0.248(3) -0.080(2) 0.018(10) Uiso 1 1 d . . . H19B H -0.098(7) -0.248(3) 0.007(2) 0.018(10) Uiso 1 1 d . . . H110 H -0.062(7) -0.074(4) -0.072(2) 0.022(10) Uiso 1 1 d . . . H12A H 0.503(7) -0.130(3) -0.062(3) 0.022(11) Uiso 1 1 d . . . H12B H 0.436(7) -0.066(4) -0.137(2) 0.021(10) Uiso 1 1 d . . . H12C H 0.516(8) -0.181(4) -0.140(3) 0.031(12) Uiso 1 1 d . . . H13A H 0.186(7) -0.227(3) -0.222(3) 0.024(11) Uiso 1 1 d . . . H13B H -0.047(9) -0.203(4) -0.187(3) 0.036(13) Uiso 1 1 d . . . H13C H 0.103(9) -0.118(5) -0.208(3) 0.045(15) Uiso 1 1 d . . . S21 S 0.0822(3) 0.11542(10) 0.83896(7) 0.0481(4) Uani 1 1 d . . . S22 S 0.40869(19) 0.24341(9) 0.77171(6) 0.0322(3) Uani 1 1 d . . . S23 S 0.03449(17) 0.19219(8) 0.68016(6) 0.0262(2) Uani 1 1 d . . . S24 S 0.61075(17) 0.35953(8) 0.65176(6) 0.0310(3) Uani 1 1 d . . . S25 S 0.14891(16) 0.29575(8) 0.54030(6) 0.0247(2) Uani 1 1 d . . . C21 C 0.1706(8) 0.1804(3) 0.7674(2) 0.0299(10) Uani 1 1 d . . . C22 C 0.3968(6) 0.2876(3) 0.6782(2) 0.0224(8) Uani 1 1 d . . . C23 C 0.2210(6) 0.2639(3) 0.6349(2) 0.0223(8) Uani 1 1 d . . . C24 C 0.4863(7) 0.4215(3) 0.5691(2) 0.0248(8) Uani 1 1 d . . . C25 C 0.3958(6) 0.3512(3) 0.5064(2) 0.0216(8) Uani 1 1 d . . . C26 C 0.5529(7) 0.2681(3) 0.4850(2) 0.0251(9) Uani 1 1 d . . . C27 C 0.5772(7) 0.2531(4) 0.3979(3) 0.0286(9) Uani 1 1 d . . . C28 C 0.4583(7) 0.3306(3) 0.3483(2) 0.0282(9) Uani 1 1 d . . . C29 C 0.2300(6) 0.3378(3) 0.3737(2) 0.0226(8) Uani 1 1 d . . . C210 C 0.3181(6) 0.4119(3) 0.4361(2) 0.0212(8) Uani 1 1 d . . . C211 C 0.4970(6) 0.4363(3) 0.3806(2) 0.0255(9) Uani 1 1 d . . . C212 C 0.7217(7) 0.4657(4) 0.4101(3) 0.0304(10) Uani 1 1 d . . . C213 C 0.4214(9) 0.5171(4) 0.3238(3) 0.0355(11) Uani 1 1 d . . . H24A H 0.376(7) 0.467(3) 0.588(2) 0.017(10) Uiso 1 1 d . . . H24B H 0.586(9) 0.463(4) 0.554(3) 0.048(16) Uiso 1 1 d . . . H26A H 0.520(5) 0.206(3) 0.5080(19) 0.001(8) Uiso 1 1 d . . . H26B H 0.695(8) 0.285(3) 0.509(2) 0.024(11) Uiso 1 1 d . . . H27A H 0.725(7) 0.248(3) 0.388(2) 0.020(10) Uiso 1 1 d . . . H27B H 0.510(8) 0.187(4) 0.385(3) 0.042(14) Uiso 1 1 d . . . H28 H 0.477(6) 0.324(3) 0.294(2) 0.009(9) Uiso 1 1 d . . . H29A H 0.141(6) 0.369(3) 0.337(2) 0.016(10) Uiso 1 1 d . . . H29B H 0.164(7) 0.274(3) 0.394(2) 0.016(10) Uiso 1 1 d . . . H210 H 0.233(7) 0.469(3) 0.449(2) 0.018(10) Uiso 1 1 d . . . H22A H 0.721(9) 0.530(5) 0.440(4) 0.058(17) Uiso 1 1 d . . . H22B H 0.816(7) 0.476(3) 0.366(2) 0.016(10) Uiso 1 1 d . . . H22C H 0.795(8) 0.410(4) 0.448(3) 0.035(13) Uiso 1 1 d . . . H23A H 0.507(8) 0.518(4) 0.278(3) 0.032(12) Uiso 1 1 d . . . H23B H 0.280(10) 0.506(4) 0.303(3) 0.051(16) Uiso 1 1 d . . . H23C H 0.424(9) 0.587(5) 0.349(3) 0.057(16) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S11 0.0297(5) 0.0274(6) 0.0229(5) -0.0006(4) 0.0041(4) 0.0026(4) S12 0.0240(5) 0.0227(5) 0.0239(5) -0.0011(4) 0.0018(4) -0.0028(4) S13 0.0209(5) 0.0266(5) 0.0247(5) -0.0017(4) 0.0061(4) -0.0025(4) S14 0.0209(5) 0.0280(5) 0.0235(5) -0.0021(4) 0.0036(4) -0.0075(4) S15 0.0179(4) 0.0288(5) 0.0253(5) -0.0055(4) 0.0036(4) -0.0033(4) C11 0.0211(19) 0.022(2) 0.0251(19) 0.0020(17) 0.0009(16) 0.0033(17) C12 0.0215(18) 0.021(2) 0.0225(19) -0.0002(16) 0.0012(15) -0.0031(16) C13 0.0222(18) 0.0171(19) 0.028(2) -0.0049(16) 0.0061(16) 0.0051(16) C14 0.0200(19) 0.023(2) 0.023(2) -0.0012(17) -0.0004(16) -0.0037(17) C15 0.0186(18) 0.020(2) 0.0219(18) 0.0001(15) 0.0043(15) 0.0007(15) C16 0.022(2) 0.021(2) 0.026(2) 0.0022(16) -0.0012(17) 0.0064(16) C17 0.022(2) 0.023(2) 0.038(2) -0.0014(19) 0.0051(18) 0.0053(17) C18 0.026(2) 0.019(2) 0.037(2) -0.0070(18) 0.0040(18) 0.0000(17) C19 0.0171(19) 0.024(2) 0.033(2) -0.0039(18) -0.0007(18) 0.0000(16) C110 0.0140(17) 0.021(2) 0.028(2) -0.0004(17) 0.0006(16) -0.0009(16) C111 0.0199(19) 0.030(2) 0.0229(19) -0.0019(17) 0.0001(16) -0.0018(17) C112 0.025(2) 0.037(3) 0.024(2) -0.006(2) 0.0022(18) -0.0026(19) C113 0.030(2) 0.047(3) 0.029(2) -0.009(2) -0.004(2) 0.001(2) S21 0.0750(10) 0.0430(7) 0.0271(6) 0.0112(6) 0.0108(6) 0.0035(7) S22 0.0456(7) 0.0274(5) 0.0224(5) -0.0030(4) -0.0094(5) 0.0068(5) S23 0.0290(5) 0.0263(5) 0.0234(5) 0.0044(4) 0.0036(4) 0.0007(4) S24 0.0268(5) 0.0294(6) 0.0355(6) -0.0005(5) -0.0113(4) -0.0049(4) S25 0.0190(5) 0.0335(6) 0.0211(5) 0.0050(4) -0.0028(4) -0.0068(4) C21 0.048(3) 0.020(2) 0.021(2) 0.0005(17) 0.0051(19) 0.0070(19) C22 0.026(2) 0.0175(19) 0.0235(19) 0.0003(16) -0.0039(16) 0.0010(16) C23 0.025(2) 0.023(2) 0.0191(18) -0.0003(16) 0.0008(16) 0.0026(16) C24 0.022(2) 0.020(2) 0.032(2) 0.0036(19) -0.0030(17) -0.0040(18) C25 0.0153(17) 0.021(2) 0.028(2) 0.0007(17) 0.0008(16) -0.0031(15) C26 0.023(2) 0.023(2) 0.029(2) 0.0041(17) 0.0007(17) 0.0035(16) C27 0.023(2) 0.026(2) 0.037(2) -0.0002(19) 0.0031(18) 0.0034(18) C28 0.029(2) 0.031(2) 0.025(2) 0.0006(18) 0.0064(18) 0.0025(18) C29 0.0198(18) 0.025(2) 0.0224(19) 0.0057(17) -0.0025(16) -0.0015(17) C210 0.0181(18) 0.024(2) 0.0218(18) 0.0044(17) -0.0011(15) 0.0013(16) C211 0.022(2) 0.024(2) 0.031(2) 0.0025(18) 0.0071(17) 0.0004(17) C212 0.018(2) 0.029(2) 0.045(3) 0.005(2) 0.008(2) -0.0038(17) C213 0.041(3) 0.028(3) 0.038(3) 0.010(2) 0.013(2) 0.001(2) _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 C11 1.647(4) . ? S12 C11 1.725(4) . ? S12 C12 1.740(4) . ? S13 C11 1.734(4) . ? S13 C13 1.756(4) . ? S14 C12 1.742(4) . ? S14 C14 1.809(4) . ? S15 C13 1.754(4) . ? S15 C15 1.857(4) . ? C12 C13 1.350(5) . ? C14 C15 1.537(5) . ? C15 C110 1.538(5) . ? C15 C16 1.558(5) . ? C16 C17 1.553(6) . ? C17 C18 1.527(6) . ? C18 C19 1.545(6) . ? C18 C111 1.557(6) . ? C19 C110 1.548(6) . ? C110 C111 1.573(5) . ? C111 C112 1.517(6) . ? C111 C113 1.523(6) . ? S21 C21 1.650(4) . ? S22 C21 1.725(5) . ? S22 C22 1.741(4) . ? S23 C21 1.720(5) . ? S23 C23 1.746(4) . ? S24 C22 1.746(4) . ? S24 C24 1.813(4) . ? S25 C23 1.747(4) . ? S25 C25 1.856(4) . ? C22 C23 1.350(6) . ? C24 C25 1.536(6) . ? C25 C210 1.537(5) . ? C25 C26 1.555(6) . ? C26 C27 1.553(6) . ? C27 C28 1.529(6) . ? C28 C29 1.535(6) . ? C28 C211 1.545(6) . ? C29 C210 1.560(6) . ? C210 C211 1.564(5) . ? C211 C213 1.532(6) . ? C211 C212 1.537(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C11 S12 C12 97.80(18) . . ? C11 S13 C13 97.61(19) . . ? C12 S14 C14 99.94(19) . . ? C13 S15 C15 101.53(18) . . ? S11 C11 S12 123.3(2) . . ? S11 C11 S13 124.1(2) . . ? S12 C11 S13 112.6(2) . . ? C13 C12 S12 116.5(3) . . ? C13 C12 S14 128.2(3) . . ? S12 C12 S14 115.3(2) . . ? C12 C13 S15 129.2(3) . . ? C12 C13 S13 115.3(3) . . ? S15 C13 S13 115.4(2) . . ? C15 C14 S14 115.2(3) . . ? C14 C15 C110 110.7(3) . . ? C14 C15 C16 113.2(3) . . ? C110 C15 C16 111.6(3) . . ? C14 C15 S15 107.5(3) . . ? C110 C15 S15 102.2(2) . . ? C16 C15 S15 111.0(3) . . ? C17 C16 C15 115.8(3) . . ? C18 C17 C16 113.3(3) . . ? C17 C18 C19 107.8(3) . . ? C17 C18 C111 112.1(3) . . ? C19 C18 C111 87.8(3) . . ? C18 C19 C110 86.6(3) . . ? C15 C110 C19 108.4(3) . . ? C15 C110 C111 113.4(3) . . ? C19 C110 C111 87.1(3) . . ? C112 C111 C113 107.3(4) . . ? C112 C111 C18 117.7(4) . . ? C113 C111 C18 111.6(4) . . ? C112 C111 C110 123.0(3) . . ? C113 C111 C110 110.4(3) . . ? C18 C111 C110 85.4(3) . . ? C21 S22 C22 97.6(2) . . ? C21 S23 C23 97.8(2) . . ? C22 S24 C24 99.03(19) . . ? C23 S25 C25 102.72(19) . . ? S21 C21 S23 123.4(3) . . ? S21 C21 S22 123.8(3) . . ? S23 C21 S22 112.8(2) . . ? C23 C22 S22 116.2(3) . . ? C23 C22 S24 127.5(3) . . ? S22 C22 S24 116.3(2) . . ? C22 C23 S23 115.5(3) . . ? C22 C23 S25 129.8(3) . . ? S23 C23 S25 114.7(2) . . ? C25 C24 S24 114.6(3) . . ? C24 C25 C210 109.7(3) . . ? C24 C25 C26 113.4(3) . . ? C210 C25 C26 111.7(3) . . ? C24 C25 S25 107.9(3) . . ? C210 C25 S25 103.4(2) . . ? C26 C25 S25 110.3(3) . . ? C27 C26 C25 115.4(3) . . ? C28 C27 C26 113.5(4) . . ? C27 C28 C29 108.7(3) . . ? C27 C28 C211 110.9(4) . . ? C29 C28 C211 88.2(3) . . ? C28 C29 C210 86.4(3) . . ? C25 C210 C29 108.0(3) . . ? C25 C210 C211 113.5(3) . . ? C29 C210 C211 86.7(3) . . ? C213 C211 C212 106.6(4) . . ? C213 C211 C28 112.2(4) . . ? C212 C211 C28 119.0(4) . . ? C213 C211 C210 109.9(4) . . ? C212 C211 C210 122.0(4) . . ? C28 C211 C210 85.9(3) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.305 _refine_diff_density_min -0.366 _refine_diff_density_rms 0.070 # DATA data_compound38 _database_code_depnum_ccdc_archive 'CCDC 264422' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (4aR,5R,7S,8aS)-4a,5,6,7,8,8a-Hexahydro-5,7-methano-4a,6,6-trimethyl- 1,3-dithiolo[4,5-b]-[1,4]benzodithiin-2-thione ; _chemical_name_common ; (4aR,5R,7S,8aS)-4a,5,6,7,8,8a-Hexahydro-5,7-methano-4a,6,6- trimethyl-1,3-dithiolo(4,5-b)-(1,4)benzodithiin-2-thione ; _chemical_melting_point 412-413 _chemical_formula_moiety ? _chemical_formula_sum 'C13 H16 S5' _chemical_formula_weight 332.56 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.2322(2) _cell_length_b 9.3635(2) _cell_length_c 11.3961(3) _cell_angle_alpha 90.00 _cell_angle_beta 106.4053(11) _cell_angle_gamma 90.00 _cell_volume 740.31(3) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 10374 _cell_measurement_theta_min 2.94 _cell_measurement_theta_max 27.46 _exptl_crystal_description shard _exptl_crystal_colour orange _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.492 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 348 _exptl_absorpt_coefficient_mu 0.762 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.76 _exptl_absorpt_correction_T_max 0.92 _exptl_absorpt_process_details ; Using multiple and symmetry-related data measurements via the program SORTAV See R. H. Blessing, Acta Cryst. (1995), A51, 33-38 ; _exptl_special_details ; PLEASE NOTE cell_measurement_ fields are not relevant to area detector data, the entire data set is used to refine the cell, which is indexed from all observed reflections in a 10 degree phi range. ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enraf Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Enraf Nonius KappaCCD area detector' _diffrn_measurement_method 'Phi and Omega scans to fill Ewald sphere' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10374 _diffrn_reflns_av_R_equivalents 0.0806 _diffrn_reflns_av_sigmaI/netI 0.0670 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.94 _diffrn_reflns_theta_max 27.46 _reflns_number_total 3383 _reflns_number_gt 3231 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; 'DENZO (Otwinowski and Minor, 1997)' 'COLLECT (Hooft, 1998)' ; _computing_cell_refinement ; 'DENZO (Otwinowski and Minor, 1997)' 'COLLECT (Hooft, 1998)' ; _computing_data_reduction ; 'DENZO (Otwinowski and Minor, 1997)' 'COLLECT (Hooft, 1998)' ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP3 (Johnson and Burnett, 1996)' _computing_publication_material 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0371P)^2^+0.2308P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _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 -0.08(9) _refine_ls_number_reflns 3383 _refine_ls_number_parameters 227 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0418 _refine_ls_R_factor_gt 0.0386 _refine_ls_wR_factor_ref 0.0932 _refine_ls_wR_factor_gt 0.0910 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.062 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _chemical_absolute_configuration syn 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 S1 S 0.50419(12) 0.93265(8) 0.16151(7) 0.02845(19) Uani 1 1 d . . . S2 S 0.49223(10) 0.62083(7) 0.10891(6) 0.01990(16) Uani 1 1 d . . . S3 S 0.18200(11) 0.74706(7) 0.18712(7) 0.02304(17) Uani 1 1 d . . . S4 S 0.31017(10) 0.32467(7) 0.08413(6) 0.02040(16) Uani 1 1 d . . . S5 S -0.04079(10) 0.46965(8) 0.16059(6) 0.02208(17) Uani 1 1 d . . . C1 C 0.3974(4) 0.7754(3) 0.1523(3) 0.0220(6) Uani 1 1 d . . . C2 C 0.3052(4) 0.5064(3) 0.1149(3) 0.0189(6) Uani 1 1 d . . . C3 C 0.1599(4) 0.5650(3) 0.1511(2) 0.0197(6) Uani 1 1 d . . . C4 C 0.2584(4) 0.2556(3) 0.2220(3) 0.0190(5) Uani 1 1 d . . . C5 C 0.0603(4) 0.2984(3) 0.2390(3) 0.0191(6) Uani 1 1 d . . . C6 C 0.0732(4) 0.3144(3) 0.3747(3) 0.0192(6) Uani 1 1 d . . . C7 C 0.2012(4) 0.1952(3) 0.4576(3) 0.0208(6) Uani 1 1 d . . . C8 C 0.3746(4) 0.2922(3) 0.4547(3) 0.0217(6) Uani 1 1 d . . . C9 C 0.4332(4) 0.2744(3) 0.3368(3) 0.0214(6) Uani 1 1 d . . . C10 C 0.2375(4) 0.4210(3) 0.4370(3) 0.0223(6) Uani 1 1 d . . . C11 C -0.0963(4) 0.1919(4) 0.1748(3) 0.0253(6) Uani 1 1 d . . . C12 C 0.2031(5) 0.0394(3) 0.4182(3) 0.0268(7) Uani 1 1 d . . . C13 C 0.1617(5) 0.1944(4) 0.5832(3) 0.0292(7) Uani 1 1 d . . . H11C H -0.089(5) 0.173(4) 0.085(3) 0.030(9) Uiso 1 1 d . . . H11B H -0.230(5) 0.222(4) 0.176(3) 0.030(9) Uiso 1 1 d . . . H11A H -0.085(5) 0.095(4) 0.217(3) 0.029(9) Uiso 1 1 d . . . H4 H 0.242(5) 0.147(4) 0.189(3) 0.024(8) Uiso 1 1 d . . . H9A H 0.506(4) 0.363(3) 0.327(3) 0.007(7) Uiso 1 1 d . . . H9B H 0.510(5) 0.198(4) 0.344(3) 0.025(9) Uiso 1 1 d . . . H8 H 0.493(5) 0.288(4) 0.527(3) 0.027(9) Uiso 1 1 d . . . H6 H -0.055(5) 0.330(4) 0.389(3) 0.022(8) Uiso 1 1 d . . . H10A H 0.264(4) 0.496(4) 0.390(3) 0.015(8) Uiso 1 1 d . . . H10B H 0.226(5) 0.459(4) 0.516(3) 0.029(9) Uiso 1 1 d . . . H13A H 0.024(5) 0.150(4) 0.580(3) 0.035(10) Uiso 1 1 d . . . H13B H 0.162(5) 0.288(4) 0.614(3) 0.026(9) Uiso 1 1 d . . . H13C H 0.252(5) 0.131(4) 0.643(3) 0.028(9) Uiso 1 1 d . . . H12A H 0.235(5) 0.031(4) 0.339(3) 0.027(9) Uiso 1 1 d . . . H12B H 0.078(6) -0.008(5) 0.411(4) 0.041(11) Uiso 1 1 d . . . H12C H 0.306(6) -0.011(5) 0.479(4) 0.038(10) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0376(4) 0.0189(4) 0.0305(4) -0.0009(3) 0.0124(3) -0.0014(3) S2 0.0217(3) 0.0179(3) 0.0213(4) 0.0012(3) 0.0080(3) 0.0018(3) S3 0.0286(4) 0.0185(3) 0.0244(4) 0.0003(3) 0.0114(3) 0.0058(3) S4 0.0265(3) 0.0181(3) 0.0195(3) -0.0012(3) 0.0113(3) 0.0020(3) S5 0.0175(3) 0.0272(4) 0.0217(4) 0.0043(3) 0.0057(3) 0.0049(3) C1 0.0264(14) 0.0222(14) 0.0172(14) 0.0021(11) 0.0055(11) 0.0055(12) C2 0.0215(13) 0.0188(13) 0.0167(14) 0.0041(11) 0.0058(10) 0.0033(11) C3 0.0218(13) 0.0220(13) 0.0146(13) 0.0035(11) 0.0039(10) 0.0052(11) C4 0.0204(13) 0.0182(13) 0.0188(13) -0.0001(11) 0.0063(10) 0.0010(11) C5 0.0208(13) 0.0185(14) 0.0179(14) 0.0000(11) 0.0054(11) 0.0008(11) C6 0.0191(12) 0.0228(15) 0.0154(13) 0.0001(12) 0.0046(10) -0.0002(11) C7 0.0232(13) 0.0204(14) 0.0177(14) 0.0011(11) 0.0041(10) -0.0030(11) C8 0.0217(13) 0.0221(15) 0.0175(15) 0.0045(11) -0.0007(11) -0.0014(11) C9 0.0168(12) 0.0229(14) 0.0240(15) 0.0040(11) 0.0051(11) 0.0028(12) C10 0.0274(15) 0.0198(15) 0.0187(15) -0.0021(12) 0.0051(12) -0.0042(12) C11 0.0215(14) 0.0301(16) 0.0227(15) -0.0051(13) 0.0036(11) -0.0067(13) C12 0.0350(17) 0.0191(14) 0.0276(17) 0.0053(13) 0.0111(13) 0.0004(13) C13 0.0383(18) 0.0291(17) 0.0200(15) 0.0039(14) 0.0082(13) -0.0061(15) _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 S1 C1 1.652(3) . ? S2 C1 1.732(3) . ? S2 C2 1.742(3) . ? S3 C1 1.733(3) . ? S3 C3 1.750(3) . ? S4 C2 1.740(3) . ? S4 C4 1.833(3) . ? S5 C3 1.734(3) . ? S5 C5 1.880(3) . ? C2 C3 1.349(4) . ? C4 C9 1.551(4) . ? C4 C5 1.552(4) . ? C5 C6 1.530(4) . ? C5 C11 1.531(4) . ? C6 C10 1.561(4) . ? C6 C7 1.582(4) . ? C7 C12 1.527(4) . ? C7 C13 1.537(4) . ? C7 C8 1.556(4) . ? C8 C9 1.528(4) . ? C8 C10 1.538(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 S2 C2 97.37(14) . . ? C1 S3 C3 97.11(14) . . ? C2 S4 C4 98.72(13) . . ? C3 S5 C5 104.41(13) . . ? S1 C1 S2 123.19(18) . . ? S1 C1 S3 123.78(18) . . ? S2 C1 S3 113.03(18) . . ? C3 C2 S4 121.4(2) . . ? C3 C2 S2 116.3(2) . . ? S4 C2 S2 122.21(16) . . ? C2 C3 S5 123.2(2) . . ? C2 C3 S3 116.1(2) . . ? S5 C3 S3 120.64(16) . . ? C9 C4 C5 115.3(2) . . ? C9 C4 S4 111.6(2) . . ? C5 C4 S4 115.8(2) . . ? C6 C5 C11 111.9(2) . . ? C6 C5 C4 110.9(2) . . ? C11 C5 C4 110.9(2) . . ? C6 C5 S5 107.56(19) . . ? C11 C5 S5 101.1(2) . . ? C4 C5 S5 114.2(2) . . ? C5 C6 C10 110.1(2) . . ? C5 C6 C7 113.2(2) . . ? C10 C6 C7 86.4(2) . . ? C12 C7 C13 106.8(3) . . ? C12 C7 C8 118.5(3) . . ? C13 C7 C8 112.7(2) . . ? C12 C7 C6 123.4(2) . . ? C13 C7 C6 109.2(3) . . ? C8 C7 C6 85.1(2) . . ? C9 C8 C10 107.4(2) . . ? C9 C8 C7 112.4(2) . . ? C10 C8 C7 88.1(2) . . ? C8 C9 C4 113.1(2) . . ? C8 C10 C6 86.4(2) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.317 _refine_diff_density_min -0.367 _refine_diff_density_rms 0.066 data_compound42 _database_code_depnum_ccdc_archive 'CCDC 264423' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (4aR,7R,8S,8aS)-4a,5,6,7,8,8a-Hexahydro-7,8-isopropano-4a-methyl-1,3-dithiolo [4,5-b][1,4]benzodithiin-2-thione ; _chemical_name_common ; (4aR,7R,8S,8aS)-4a,5,6,7,8,8a-Hexahydro-7,8-isopropano-4a- methyl-1,3-dithiolo (4,5-b)(1,4)benzodithiin-2-thione ; _chemical_melting_point 398-400 _chemical_formula_moiety ? _chemical_formula_sum 'C13 H16 S5' _chemical_formula_weight 332.56 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 7.60900(10) _cell_length_b 9.7890(2) _cell_length_c 20.1711(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1502.43(5) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 9971 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.470 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 696 _exptl_absorpt_coefficient_mu 0.751 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.50 _exptl_absorpt_correction_T_max 0.57 _exptl_absorpt_process_details ; Using multiple and symmetry-related data measurements via the program SORTAV See R. H. Blessing, Acta Cryst. (1995), A51, 33-38 ; _exptl_special_details ; PLEASE NOTE cell_measurement_ fields are not relevant to area detector data, the entire data set is used to refine the cell, which is indexed from all observed reflections in a 10 degree phi range. ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enraf Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Enraf Nonius KappaCCD area detector' _diffrn_measurement_method 'Phi and Omega scans to fill Ewald sphere' _diffrn_detector_area_resol_mean 9.09 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15154 _diffrn_reflns_av_R_equivalents 0.0531 _diffrn_reflns_av_sigmaI/netI 0.0353 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 3.35 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3415 _reflns_number_gt 3208 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; 'DENZO (Otwinowski and Minor, 1997)' 'COLLECT (Hooft, 1998)' ; _computing_cell_refinement ; 'DENZO (Otwinowski and Minor, 1997)' 'COLLECT (Hooft, 1998)' ; _computing_data_reduction ; 'DENZO (Otwinowski and Minor, 1997)' 'COLLECT (Hooft, 1998)' ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP3 (Johnson and Burnett, 1996)' _computing_publication_material 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0371P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _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 -0.03(6) _refine_ls_number_reflns 3415 _refine_ls_number_parameters 227 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0283 _refine_ls_R_factor_gt 0.0253 _refine_ls_wR_factor_ref 0.0603 _refine_ls_wR_factor_gt 0.0594 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _chemical_absolute_configuration syn 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 S1 S 0.58000(6) 0.38339(4) 0.84177(2) 0.02354(11) Uani 1 1 d . . . S2 S 0.33384(6) 0.57531(4) 0.90889(2) 0.01767(10) Uani 1 1 d . . . S3 S 0.58146(6) 0.68331(4) 0.81509(2) 0.02120(11) Uani 1 1 d . . . S4 S 0.17374(6) 0.83877(4) 0.94633(2) 0.01844(10) Uani 1 1 d . . . S5 S 0.49076(5) 0.97383(4) 0.83507(2) 0.01890(11) Uani 1 1 d . . . C1 C 0.5026(2) 0.53871(18) 0.85450(9) 0.0180(4) Uani 1 1 d . . . C2 C 0.3311(2) 0.75263(17) 0.89910(8) 0.0146(3) Uani 1 1 d . . . C3 C 0.4484(2) 0.80344(17) 0.85539(8) 0.0156(3) Uani 1 1 d . . . C4 C 0.2597(2) 1.01416(18) 0.94210(9) 0.0175(4) Uani 1 1 d . . . C5 C 0.2981(2) 1.05685(18) 0.86999(9) 0.0156(3) Uani 1 1 d . . . C6 C 0.1400(2) 1.04612(17) 0.82469(8) 0.0154(3) Uani 1 1 d . . . C7 C 0.0303(2) 1.17060(18) 0.80610(9) 0.0180(4) Uani 1 1 d . . . C8 C -0.0413(2) 1.06739(18) 0.85480(9) 0.0177(4) Uani 1 1 d . . . C9 C -0.0620(2) 1.0951(2) 0.92817(10) 0.0227(4) Uani 1 1 d . . . C10 C 0.1103(3) 1.1063(2) 0.96737(10) 0.0221(4) Uani 1 1 d . . . C11 C 0.0819(3) 1.31108(18) 0.82976(10) 0.0214(4) Uani 1 1 d . . . C12 C -0.0539(3) 1.1721(2) 0.73827(10) 0.0249(4) Uani 1 1 d . . . C13 C 0.4211(3) 1.0271(2) 0.98696(10) 0.0270(4) Uani 1 1 d . . . H5 H 0.342(3) 1.155(2) 0.8709(10) 0.022(5) Uiso 1 1 d . . . H6 H 0.147(3) 0.981(2) 0.7931(10) 0.016(5) Uiso 1 1 d . . . H8 H -0.128(2) 1.0114(18) 0.8372(9) 0.006(4) Uiso 1 1 d . . . H9A H -0.128(3) 1.020(2) 0.9495(10) 0.024(5) Uiso 1 1 d . . . H9B H -0.137(3) 1.176(2) 0.9367(10) 0.027(6) Uiso 1 1 d . . . H10A H 0.166(3) 1.200(2) 0.9637(10) 0.021(5) Uiso 1 1 d . . . H10B H 0.094(3) 1.088(2) 1.0136(12) 0.030(6) Uiso 1 1 d . . . H11A H 0.125(3) 1.309(2) 0.8731(10) 0.018(5) Uiso 1 1 d . . . H11B H -0.013(3) 1.369(2) 0.8306(9) 0.013(5) Uiso 1 1 d . . . H11C H 0.161(3) 1.348(2) 0.7963(12) 0.038(6) Uiso 1 1 d . . . H12A H -0.173(3) 1.220(2) 0.7373(11) 0.034(6) Uiso 1 1 d . . . H12B H -0.088(3) 1.079(2) 0.7245(11) 0.028(6) Uiso 1 1 d . . . H12C H 0.025(3) 1.221(2) 0.7055(12) 0.034(6) Uiso 1 1 d . . . H13A H 0.514(3) 0.954(2) 0.9783(11) 0.033(6) Uiso 1 1 d . . . H13B H 0.392(3) 1.012(2) 1.0379(12) 0.034(6) Uiso 1 1 d . . . H13C H 0.475(3) 1.115(3) 0.9824(11) 0.033(6) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0272(2) 0.0162(2) 0.0273(3) -0.00116(18) 0.0031(2) 0.00479(19) S2 0.0200(2) 0.0136(2) 0.0194(2) 0.00112(16) 0.00246(18) -0.00037(17) S3 0.0204(2) 0.0163(2) 0.0269(2) 0.00048(18) 0.00779(19) 0.00188(18) S4 0.0195(2) 0.0153(2) 0.0204(2) 0.00068(17) 0.00555(18) 0.00060(18) S5 0.0138(2) 0.0149(2) 0.0279(2) 0.00312(18) 0.00449(18) -0.00105(16) C1 0.0178(8) 0.0185(9) 0.0178(9) -0.0019(7) 0.0006(7) -0.0008(7) C2 0.0146(8) 0.0128(8) 0.0164(8) -0.0019(6) -0.0017(7) -0.0008(7) C3 0.0141(8) 0.0142(8) 0.0184(8) -0.0018(7) 0.0014(7) 0.0011(7) C4 0.0193(8) 0.0146(8) 0.0186(8) -0.0026(7) -0.0013(7) -0.0025(7) C5 0.0144(8) 0.0110(8) 0.0215(9) -0.0018(7) 0.0004(7) -0.0010(6) C6 0.0156(8) 0.0127(8) 0.0178(9) -0.0024(7) -0.0015(6) 0.0000(6) C7 0.0170(9) 0.0160(9) 0.0210(9) -0.0004(7) -0.0027(7) 0.0003(7) C8 0.0116(8) 0.0157(8) 0.0259(10) -0.0017(8) -0.0016(7) -0.0021(7) C9 0.0191(9) 0.0227(10) 0.0262(10) -0.0003(8) 0.0065(8) 0.0045(8) C10 0.0261(10) 0.0223(10) 0.0181(9) -0.0037(8) 0.0037(7) 0.0032(8) C11 0.0208(9) 0.0156(9) 0.0279(10) 0.0003(8) -0.0022(9) 0.0030(8) C12 0.0266(10) 0.0224(10) 0.0257(10) -0.0004(8) -0.0071(8) 0.0041(8) C13 0.0279(10) 0.0272(11) 0.0260(10) -0.0056(8) -0.0102(9) 0.0024(10) _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 S1 C1 1.6505(19) . ? S2 C1 1.7267(18) . ? S2 C2 1.7471(17) . ? S3 C1 1.7307(18) . ? S3 C3 1.7518(17) . ? S4 C2 1.7470(17) . ? S4 C4 1.8393(18) . ? S5 C3 1.7475(18) . ? S5 C5 1.8183(18) . ? C2 C3 1.350(2) . ? C4 C13 1.531(3) . ? C4 C10 1.538(2) . ? C4 C5 1.541(2) . ? C5 C6 1.514(2) . ? C6 C8 1.522(2) . ? C6 C7 1.524(2) . ? C7 C11 1.507(2) . ? C7 C12 1.511(3) . ? C7 C8 1.511(3) . ? C8 C9 1.513(3) . ? C9 C10 1.535(3) . ? 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 C1 S2 C2 98.23(9) . . ? C1 S3 C3 97.79(8) . . ? C2 S4 C4 100.46(8) . . ? C3 S5 C5 100.78(8) . . ? S1 C1 S2 123.72(11) . . ? S1 C1 S3 123.94(11) . . ? S2 C1 S3 112.33(10) . . ? C3 C2 S4 129.17(13) . . ? C3 C2 S2 115.60(13) . . ? S4 C2 S2 115.22(10) . . ? C2 C3 S5 128.82(13) . . ? C2 C3 S3 115.98(13) . . ? S5 C3 S3 115.17(9) . . ? C13 C4 C10 110.39(15) . . ? C13 C4 C5 112.55(15) . . ? C10 C4 C5 107.08(15) . . ? C13 C4 S4 109.56(14) . . ? C10 C4 S4 105.64(12) . . ? C5 C4 S4 111.37(12) . . ? C6 C5 C4 113.59(14) . . ? C6 C5 S5 112.06(12) . . ? C4 C5 S5 113.40(12) . . ? C5 C6 C8 118.03(14) . . ? C5 C6 C7 121.88(14) . . ? C8 C6 C7 59.48(12) . . ? C11 C7 C12 112.83(16) . . ? C11 C7 C8 119.87(16) . . ? C12 C7 C8 116.23(16) . . ? C11 C7 C6 120.61(15) . . ? C12 C7 C6 117.58(16) . . ? C8 C7 C6 60.20(11) . . ? C7 C8 C9 123.61(16) . . ? C7 C8 C6 60.32(12) . . ? C9 C8 C6 120.60(15) . . ? C8 C9 C10 115.34(15) . . ? C9 C10 C4 114.73(15) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.258 _refine_diff_density_min -0.403 _refine_diff_density_rms 0.078