# Supplementary Material (ESI) for ChemComm # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 182/1649 data_heli9 _audit_creation_method SHELXL-97 _chemical_name_systematic ; [9]-thiohelicene ; _chemical_name_common [9]-thiohelicene _chemical_formula_moiety 'C28 H12 S5' _chemical_formula_sum 'C28 H12 S5' _chemical_formula_weight 508.68 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 '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' 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 14.6550(10) _cell_length_b 10.6560(10) _cell_length_c 13.9760(10) _cell_angle_alpha 90.00 _cell_angle_beta 100.250(10) _cell_angle_gamma 90.00 _cell_volume 2147.7(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 58 _cell_measurement_theta_min 12.6 _cell_measurement_theta_max 31.3 _exptl_crystal_description 'needle' _exptl_crystal_colour 'light brown' _exptl_crystal_size_max 0.8 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.573 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1040 _exptl_absorpt_coefficient_mu 5.098 _exptl_absorpt_correction_type 'empirical via \y-scan' _exptl_absorpt_correction_T_min 0.1648 _exptl_absorpt_correction_T_max 0.7131 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Siemens P4' _diffrn_measurement_method \q/2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 250 _diffrn_standards_interval_time ? _diffrn_standards_decay_% <0.3 _diffrn_reflns_number 3662 _diffrn_reflns_av_R_equivalents 0.0780 _diffrn_reflns_av_sigmaI/netI 0.0772 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 5.16 _diffrn_reflns_theta_max 67.92 _reflns_number_total 1875 _reflns_number_gt 1760 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'XSCANS (Siemens, 1994)' _computing_cell_refinement 'xscans (Siemens, 1994)' _computing_data_reduction 'Xscans (Siemens, 1994)' _computing_structure_solution 'SIR97 (Altomare et al.1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL/PC (Sheldrick, 1994)' _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. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0597P)^2^+1.5730P] 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 SHELXL _refine_ls_extinction_coef 0.0021(2) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 1875 _refine_ls_number_parameters 175 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0487 _refine_ls_R_factor_gt 0.0423 _refine_ls_wR_factor_ref 0.1248 _refine_ls_wR_factor_gt 0.1218 _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_restrained_S_all 1.073 _refine_ls_shift/su_max 2.639 _refine_ls_shift/su_mean 0.110 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.18469(5) 0.86925(6) 0.21681(5) 0.0566(3) Uani 1 d . . . S2 S -0.16136(4) 0.60993(6) -0.01265(4) 0.0454(2) Uani 1 d . . . S3 S 0.0000 0.16722(7) 0.2500 0.0462(3) Uani 1 d S . . C1 C 0.21772(15) 0.7188(3) 0.25220(18) 0.0484(6) Uani 1 d D . . H1 H 0.2866(11) 0.700(3) 0.2905(19) 0.061(9) Uiso 1 d D . . C2 C 0.15046(14) 0.6329(2) 0.22574(16) 0.0367(5) Uani 1 d D . . H2 H 0.1624(15) 0.5354(10) 0.2381(16) 0.035(6) Uiso 1 d D . . C3 C 0.06714(13) 0.68769(19) 0.17258(14) 0.0306(4) Uani 1 d . . . C4 C 0.07699(15) 0.8171(2) 0.15918(16) 0.0386(5) Uani 1 d . . . C5 C 0.00976(19) 0.8899(2) 0.09940(19) 0.0470(6) Uani 1 d D . . H5 H 0.019(2) 0.9887(11) 0.092(2) 0.062(8) Uiso 1 d D . . C6 C -0.06575(17) 0.8310(2) 0.04616(18) 0.0437(5) Uani 1 d D . . H6 H -0.1107(18) 0.880(3) -0.0106(17) 0.068(9) Uiso 1 d D . . C7 C -0.07640(14) 0.7009(2) 0.05777(15) 0.0358(5) Uani 1 d . . . C8 C -0.01690(13) 0.62983(18) 0.12682(14) 0.0295(4) Uani 1 d . . . C9 C -0.04946(12) 0.50192(19) 0.13113(14) 0.0291(4) Uani 1 d . . . C10 C -0.12039(13) 0.4759(2) 0.05137(15) 0.0353(5) Uani 1 d . . . C11 C -0.15220(15) 0.3535(2) 0.02743(17) 0.0416(5) Uani 1 d . . . H11 H -0.199(2) 0.340(3) -0.034(2) 0.067(9) Uiso 1 d . . . C12 C -0.11368(15) 0.2559(2) 0.08316(17) 0.0416(5) Uani 1 d . . . H12 H -0.131(3) 0.167(3) 0.057(3) 0.081(11) Uiso 1 d . . . C13 C -0.05154(14) 0.28131(19) 0.16918(16) 0.0354(5) Uani 1 d . . . C14 C -0.02503(13) 0.40437(19) 0.20028(14) 0.0291(4) Uani 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 0.0503(4) 0.0486(4) 0.0710(5) -0.0086(3) 0.0114(3) -0.0255(3) S2 0.0344(3) 0.0547(4) 0.0424(4) 0.0081(2) -0.0062(2) -0.0018(2) S3 0.0540(5) 0.0223(4) 0.0630(6) 0.000 0.0120(4) 0.000 C1 0.0302(10) 0.0624(16) 0.0519(13) -0.0049(11) 0.0054(10) -0.0127(10) C2 0.0269(10) 0.0450(13) 0.0387(11) -0.0007(9) 0.0075(8) -0.0046(8) C3 0.0289(9) 0.0305(10) 0.0333(10) -0.0007(8) 0.0078(8) -0.0043(7) C4 0.0402(11) 0.0327(11) 0.0457(12) -0.0028(9) 0.0152(9) -0.0079(8) C5 0.0579(14) 0.0282(11) 0.0589(15) 0.0048(10) 0.0210(12) 0.0015(10) C6 0.0456(12) 0.0370(12) 0.0490(13) 0.0121(10) 0.0094(10) 0.0071(9) C7 0.0309(10) 0.0382(12) 0.0378(11) 0.0060(8) 0.0045(8) 0.0012(8) C8 0.0264(9) 0.0292(10) 0.0335(10) 0.0019(7) 0.0071(8) 0.0000(7) C9 0.0241(8) 0.0302(10) 0.0331(10) -0.0003(7) 0.0051(7) -0.0022(7) C10 0.0269(9) 0.0424(12) 0.0361(10) -0.0003(8) 0.0044(8) -0.0058(8) C11 0.0331(10) 0.0506(14) 0.0407(11) -0.0107(10) 0.0056(9) -0.0143(9) C12 0.0400(11) 0.0374(12) 0.0487(12) -0.0136(10) 0.0117(10) -0.0134(9) C13 0.0364(10) 0.0259(10) 0.0455(12) -0.0046(8) 0.0115(9) -0.0042(8) C14 0.0266(9) 0.0245(9) 0.0371(11) -0.0011(8) 0.0078(8) -0.0015(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 S1 C1 1.721(3) . ? S1 C4 1.731(2) . ? S2 C10 1.735(2) . ? S2 C7 1.738(2) . ? S3 C13 1.738(2) 2 ? S3 C13 1.738(2) . ? C1 C2 1.348(3) . ? C1 H1 1.073(10) . ? C2 C3 1.436(3) . ? C2 H2 1.062(10) . ? C3 C4 1.403(3) . ? C3 C8 1.423(3) . ? C4 C5 1.406(3) . ? C5 C6 1.371(4) . ? C5 H5 1.069(10) . ? C6 C7 1.407(3) . ? C6 H6 1.070(10) . ? C7 C8 1.402(3) . ? C8 C9 1.449(3) . ? C9 C10 1.410(3) . ? C9 C14 1.421(3) . ? C10 C11 1.405(3) . ? C11 C12 1.361(4) . ? C11 H11 1.01(3) . ? C12 C13 1.399(3) . ? C12 H12 1.03(4) . ? C13 C14 1.414(3) . ? C14 C14 1.451(4) 2 ? 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 S1 C4 91.23(11) . . ? C10 S2 C7 91.13(10) . . ? C13 S3 C13 91.23(14) 2 . ? C2 C1 S1 113.54(18) . . ? C2 C1 H1 125.9(17) . . ? S1 C1 H1 120.5(17) . . ? C1 C2 C3 112.2(2) . . ? C1 C2 H2 121.9(12) . . ? C3 C2 H2 125.6(12) . . ? C4 C3 C8 117.86(18) . . ? C4 C3 C2 111.77(18) . . ? C8 C3 C2 130.13(19) . . ? C3 C4 C5 122.9(2) . . ? C3 C4 S1 111.12(16) . . ? C5 C4 S1 125.73(18) . . ? C6 C5 C4 118.8(2) . . ? C6 C5 H5 120.0(16) . . ? C4 C5 H5 121.0(16) . . ? C5 C6 C7 119.0(2) . . ? C5 C6 H6 120.7(17) . . ? C7 C6 H6 119.7(17) . . ? C8 C7 C6 122.89(19) . . ? C8 C7 S2 112.56(16) . . ? C6 C7 S2 124.52(17) . . ? C7 C8 C3 117.25(18) . . ? C7 C8 C9 111.56(17) . . ? C3 C8 C9 130.84(18) . . ? C10 C9 C14 117.07(18) . . ? C10 C9 C8 110.73(18) . . ? C14 C9 C8 132.17(17) . . ? C11 C10 C9 122.5(2) . . ? C11 C10 S2 124.86(17) . . ? C9 C10 S2 112.63(16) . . ? C12 C11 C10 119.2(2) . . ? C12 C11 H11 122.0(18) . . ? C10 C11 H11 118.6(18) . . ? C11 C12 C13 118.9(2) . . ? C11 C12 H12 117(2) . . ? C13 C12 H12 124(2) . . ? C12 C13 C14 123.0(2) . . ? C12 C13 S3 124.33(17) . . ? C14 C13 S3 112.65(15) . . ? C13 C14 C9 116.55(18) . . ? C13 C14 C14 111.02(12) . 2 ? C9 C14 C14 132.41(11) . 2 ? 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 C2 C3 C8 C9 10.0(4) . . . . ? C3 C8 C9 C14 21.7(4) . . . . ? C8 C9 C14 C14 15.6(4) . . . 2 ? C9 C14 C14 C9 15.7(5) . . 2 2 ? C14 C14 C9 C8 15.6(4) . 2 2 2 ? C14 C9 C8 C3 21.7(4) 2 2 2 2 ? C9 C8 C3 C2 10.0(4) 2 2 2 2 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C2 H2 S1 1.062(10) 2.838(17) 3.699(2) 138.3(16) 4_545 _diffrn_measured_fraction_theta_max 0.452 _diffrn_reflns_theta_full 67.92 _diffrn_measured_fraction_theta_full 0.452 _refine_diff_density_max 0.304 _refine_diff_density_min -0.455 _refine_diff_density_rms 0.072