# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Honggang Cheng' _publ_contact_author_email chg0283@126.com loop_ _publ_author_name 'Wen-Jing Xiao' 'Honggang Cheng' data_t _database_code_depnum_ccdc_archive 'CCDC 852993' #TrackingRef 't.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H24 Cl N O2 S' _chemical_formula_weight 473.99 _chemical_absolute_configuration ad 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' O O 0.0106 0.0060 '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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 12.290(4) _cell_length_b 5.9017(17) _cell_length_c 16.991(5) _cell_angle_alpha 90.00 _cell_angle_beta 104.225(5) _cell_angle_gamma 90.00 _cell_volume 1194.6(6) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2206 _cell_measurement_theta_min 2.64 _cell_measurement_theta_max 23.53 _exptl_crystal_description block _exptl_crystal_colour ? _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.318 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 496 _exptl_absorpt_coefficient_mu 0.273 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9476 _exptl_absorpt_correction_T_max 0.9732 _exptl_absorpt_process_details 'SADABS, Sheldrick,1997' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 5919 _diffrn_reflns_av_R_equivalents 0.0341 _diffrn_reflns_av_sigmaI/netI 0.0533 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.85 _diffrn_reflns_theta_max 23.98 _reflns_number_total 3512 _reflns_number_gt 3054 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0481P)^2^+0.5010P] 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(1) _refine_ls_number_reflns 3512 _refine_ls_number_parameters 302 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0533 _refine_ls_R_factor_gt 0.0432 _refine_ls_wR_factor_ref 0.1252 _refine_ls_wR_factor_gt 0.1129 _refine_ls_goodness_of_fit_ref 1.125 _refine_ls_restrained_S_all 1.124 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 C1 C 0.6408(3) 0.9604(8) 0.4682(2) 0.0438(10) Uani 1 1 d . . . C2 C 0.6660(3) 1.1752(8) 0.4473(3) 0.0501(11) Uani 1 1 d . . . H2 H 0.7354 1.2396 0.4711 0.060 Uiso 1 1 calc R . . C3 C 0.5874(4) 1.2938(8) 0.3906(3) 0.0540(11) Uani 1 1 d . . . H3 H 0.6039 1.4402 0.3770 0.065 Uiso 1 1 calc R . . C4 C 0.4838(3) 1.1996(8) 0.3533(2) 0.0433(9) Uani 1 1 d . . . C5 C 0.4590(3) 0.9795(7) 0.3759(2) 0.0364(9) Uani 1 1 d . . . C6 C 0.5384(3) 0.8623(7) 0.4339(2) 0.0409(9) Uani 1 1 d . . . H6 H 0.5224 0.7176 0.4496 0.049 Uiso 1 1 calc R . . C7 C 0.3538(3) 0.8722(7) 0.3371(2) 0.0386(9) Uani 1 1 d . . . H7 H 0.3416 0.7243 0.3518 0.046 Uiso 1 1 calc R . . C8 C 0.1741(3) 0.8399(7) 0.2483(2) 0.0367(9) Uani 1 1 d . . . H8 H 0.1915 0.6778 0.2542 0.044 Uiso 1 1 calc R . . C9 C 0.0887(3) 0.8959(7) 0.2968(2) 0.0383(9) Uani 1 1 d . . . C10 C 0.0357(4) 1.1042(8) 0.2919(3) 0.0468(10) Uani 1 1 d . . . H10 H 0.0498 1.2140 0.2564 0.056 Uiso 1 1 calc R . . C11 C -0.0376(4) 1.1494(9) 0.3390(3) 0.0577(13) Uani 1 1 d . . . H11 H -0.0736 1.2891 0.3346 0.069 Uiso 1 1 calc R . . C12 C -0.0589(4) 0.9913(11) 0.3929(3) 0.0628(14) Uani 1 1 d . . . H12 H -0.1079 1.0246 0.4252 0.075 Uiso 1 1 calc R . . C13 C -0.0069(4) 0.7840(11) 0.3986(3) 0.0695(15) Uani 1 1 d . . . H13 H -0.0215 0.6755 0.4343 0.083 Uiso 1 1 calc R . . C14 C 0.0668(4) 0.7365(8) 0.3513(2) 0.0521(12) Uani 1 1 d . . . H14 H 0.1023 0.5962 0.3559 0.063 Uiso 1 1 calc R . . C15 C 0.1389(3) 0.8976(7) 0.1573(2) 0.0373(9) Uani 1 1 d . . . H15 H 0.1068 1.0504 0.1511 0.045 Uiso 1 1 calc R . . C16 C 0.2341(3) 0.8895(7) 0.1165(2) 0.0382(9) Uani 1 1 d . . . C17 C 0.2508(4) 1.0666(8) 0.0673(3) 0.0492(11) Uani 1 1 d . . . H17 H 0.2036 1.1919 0.0615 0.059 Uiso 1 1 calc R . . C18 C 0.3342(4) 1.0632(10) 0.0272(3) 0.0615(13) Uani 1 1 d . . . H18 H 0.3421 1.1819 -0.0070 0.074 Uiso 1 1 calc R . . C19 C 0.4068(4) 0.8806(10) 0.0381(3) 0.0635(14) Uani 1 1 d . . . H19 H 0.4658 0.8781 0.0127 0.076 Uiso 1 1 calc R . . C20 C 0.3917(4) 0.7042(10) 0.0860(3) 0.0614(12) Uani 1 1 d . . . H20 H 0.4394 0.5798 0.0916 0.074 Uiso 1 1 calc R . . C21 C 0.3076(4) 0.7060(9) 0.1263(2) 0.0498(10) Uani 1 1 d . . . H21 H 0.2998 0.5858 0.1599 0.060 Uiso 1 1 calc R . . C22 C -0.0882(3) 0.7863(8) 0.1302(2) 0.0411(9) Uani 1 1 d . . . C23 C -0.1383(4) 0.9929(9) 0.1034(3) 0.0539(11) Uani 1 1 d . . . H23 H -0.1095 1.0841 0.0687 0.065 Uiso 1 1 calc R . . C24 C -0.2315(4) 1.0605(10) 0.1290(3) 0.0713(16) Uani 1 1 d . . . H24 H -0.2654 1.1980 0.1107 0.086 Uiso 1 1 calc R . . C25 C -0.2747(4) 0.9342(12) 0.1795(3) 0.0713(17) Uani 1 1 d . . . C26 C -0.2275(4) 0.7254(12) 0.2028(3) 0.0698(16) Uani 1 1 d . . . H26 H -0.2590 0.6332 0.2357 0.084 Uiso 1 1 calc R . . C27 C -0.1352(4) 0.6501(8) 0.1788(3) 0.0540(12) Uani 1 1 d . . . H27 H -0.1046 0.5085 0.1951 0.065 Uiso 1 1 calc R . . C28 C -0.3718(5) 1.0175(18) 0.2143(5) 0.133(4) Uani 1 1 d . . . H28A H -0.3424 1.0740 0.2683 0.199 Uiso 1 1 calc R . . H28B H -0.4222 0.8941 0.2157 0.199 Uiso 1 1 calc R . . H28C H -0.4115 1.1365 0.1806 0.199 Uiso 1 1 calc R . . Cl1 Cl 0.74000(9) 0.8016(2) 0.53771(7) 0.0665(4) Uani 1 1 d . . . N1 N 0.2772(3) 0.9693(6) 0.28411(18) 0.0385(8) Uani 1 1 d . . . O1 O 0.4109(3) 1.3216(6) 0.2964(2) 0.0632(9) Uani 1 1 d D . . H1 H 0.350(3) 1.261(11) 0.277(3) 0.095 Uiso 1 1 d D . . O2 O 0.0625(3) 0.4648(5) 0.1349(2) 0.0598(8) Uani 1 1 d . . . S1 S 0.03246(9) 0.69610(19) 0.09926(6) 0.0443(3) Uani 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 C1 0.040(2) 0.048(3) 0.045(2) -0.006(2) 0.0126(18) 0.004(2) C2 0.038(2) 0.050(3) 0.065(3) -0.023(3) 0.017(2) -0.012(2) C3 0.063(3) 0.037(2) 0.072(3) -0.009(2) 0.034(2) -0.009(2) C4 0.053(2) 0.032(2) 0.050(2) -0.001(2) 0.0215(19) 0.005(2) C5 0.037(2) 0.036(2) 0.039(2) -0.0007(17) 0.0140(17) 0.0075(18) C6 0.046(2) 0.037(2) 0.042(2) 0.0019(18) 0.0158(18) -0.0030(19) C7 0.042(2) 0.033(2) 0.043(2) -0.0029(18) 0.0154(18) 0.0020(18) C8 0.042(2) 0.029(2) 0.0373(19) 0.0034(17) 0.0062(16) 0.0019(17) C9 0.042(2) 0.041(2) 0.0287(19) 0.0001(17) 0.0038(16) -0.0066(18) C10 0.054(3) 0.043(3) 0.045(2) -0.0014(19) 0.017(2) -0.001(2) C11 0.062(3) 0.066(4) 0.048(3) -0.006(2) 0.019(2) 0.013(2) C12 0.060(3) 0.089(4) 0.043(3) -0.008(3) 0.021(2) 0.000(3) C13 0.078(3) 0.092(5) 0.043(3) 0.014(3) 0.024(2) -0.013(3) C14 0.057(3) 0.057(3) 0.039(2) 0.007(2) 0.0066(19) -0.006(2) C15 0.047(2) 0.029(2) 0.037(2) 0.0019(16) 0.0132(17) 0.0024(17) C16 0.044(2) 0.036(2) 0.0326(19) -0.0043(17) 0.0055(16) -0.0005(18) C17 0.052(3) 0.045(3) 0.052(3) 0.009(2) 0.016(2) -0.002(2) C18 0.068(3) 0.073(4) 0.048(3) 0.010(2) 0.021(2) -0.004(3) C19 0.056(3) 0.082(4) 0.060(3) -0.010(3) 0.028(2) -0.014(3) C20 0.058(3) 0.065(3) 0.067(3) -0.012(3) 0.027(2) 0.008(3) C21 0.061(3) 0.045(2) 0.047(2) 0.001(2) 0.021(2) 0.004(2) C22 0.042(2) 0.049(2) 0.0306(19) -0.0058(18) 0.0047(16) -0.002(2) C23 0.056(3) 0.057(3) 0.044(2) 0.004(2) 0.005(2) 0.005(2) C24 0.053(3) 0.073(4) 0.076(4) -0.021(3) -0.006(3) 0.016(3) C25 0.041(3) 0.111(5) 0.059(3) -0.045(3) 0.006(2) 0.001(3) C26 0.056(3) 0.108(5) 0.048(3) -0.015(3) 0.019(2) -0.024(3) C27 0.057(3) 0.053(3) 0.051(2) -0.005(2) 0.012(2) -0.005(2) C28 0.058(4) 0.223(11) 0.124(6) -0.078(7) 0.035(4) 0.012(5) Cl1 0.0491(6) 0.0712(8) 0.0695(8) 0.0060(6) -0.0040(5) -0.0032(6) N1 0.0428(19) 0.0345(18) 0.0372(17) -0.0047(15) 0.0081(15) 0.0021(16) O1 0.066(2) 0.042(2) 0.078(2) 0.0189(18) 0.0119(18) 0.0065(17) O2 0.062(2) 0.0310(16) 0.086(2) -0.0096(16) 0.0179(17) 0.0025(15) S1 0.0472(6) 0.0447(6) 0.0421(5) -0.0089(5) 0.0133(4) -0.0013(5) _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 C1 C2 1.373(7) . ? C1 C6 1.378(6) . ? C1 Cl1 1.747(4) . ? C2 C3 1.376(7) . ? C2 H2 0.9300 . ? C3 C4 1.391(6) . ? C3 H3 0.9300 . ? C4 O1 1.353(5) . ? C4 C5 1.409(6) . ? C5 C6 1.389(6) . ? C5 C7 1.446(6) . ? C6 H6 0.9300 . ? C7 N1 1.269(5) . ? C7 H7 0.9300 . ? C8 N1 1.477(5) . ? C8 C9 1.521(5) . ? C8 C15 1.537(5) . ? C8 H8 0.9800 . ? C9 C10 1.384(6) . ? C9 C14 1.393(6) . ? C10 C11 1.371(6) . ? C10 H10 0.9300 . ? C11 C12 1.376(7) . ? C11 H11 0.9300 . ? C12 C13 1.372(8) . ? C12 H12 0.9300 . ? C13 C14 1.379(6) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C15 C16 1.500(5) . ? C15 S1 1.861(4) . ? C15 H15 0.9800 . ? C16 C17 1.384(6) . ? C16 C21 1.394(6) . ? C17 C18 1.364(6) . ? C17 H17 0.9300 . ? C18 C19 1.382(8) . ? C18 H18 0.9300 . ? C19 C20 1.362(8) . ? C19 H19 0.9300 . ? C20 C21 1.372(6) . ? C20 H20 0.9300 . ? C21 H21 0.9300 . ? C22 C27 1.377(6) . ? C22 C23 1.391(6) . ? C22 S1 1.773(4) . ? C23 C24 1.381(7) . ? C23 H23 0.9300 . ? C24 C25 1.340(8) . ? C24 H24 0.9300 . ? C25 C26 1.378(9) . ? C25 C28 1.537(7) . ? C26 C27 1.370(7) . ? C26 H26 0.9300 . ? C27 H27 0.9300 . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? O1 H1 0.82(2) . ? O2 S1 1.502(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 C2 C1 C6 121.3(4) . . ? C2 C1 Cl1 120.4(3) . . ? C6 C1 Cl1 118.3(3) . . ? C1 C2 C3 119.1(4) . . ? C1 C2 H2 120.5 . . ? C3 C2 H2 120.5 . . ? C2 C3 C4 121.5(5) . . ? C2 C3 H3 119.3 . . ? C4 C3 H3 119.3 . . ? O1 C4 C3 119.0(4) . . ? O1 C4 C5 122.4(4) . . ? C3 C4 C5 118.6(4) . . ? C6 C5 C4 119.5(4) . . ? C6 C5 C7 119.9(4) . . ? C4 C5 C7 120.6(4) . . ? C1 C6 C5 120.0(4) . . ? C1 C6 H6 120.0 . . ? C5 C6 H6 120.0 . . ? N1 C7 C5 123.4(4) . . ? N1 C7 H7 118.3 . . ? C5 C7 H7 118.3 . . ? N1 C8 C9 107.5(3) . . ? N1 C8 C15 107.5(3) . . ? C9 C8 C15 115.8(3) . . ? N1 C8 H8 108.6 . . ? C9 C8 H8 108.6 . . ? C15 C8 H8 108.6 . . ? C10 C9 C14 118.3(4) . . ? C10 C9 C8 122.5(4) . . ? C14 C9 C8 119.1(4) . . ? C11 C10 C9 120.3(4) . . ? C11 C10 H10 119.8 . . ? C9 C10 H10 119.8 . . ? C10 C11 C12 121.1(5) . . ? C10 C11 H11 119.5 . . ? C12 C11 H11 119.5 . . ? C13 C12 C11 119.4(4) . . ? C13 C12 H12 120.3 . . ? C11 C12 H12 120.3 . . ? C12 C13 C14 120.1(5) . . ? C12 C13 H13 120.0 . . ? C14 C13 H13 120.0 . . ? C13 C14 C9 120.8(5) . . ? C13 C14 H14 119.6 . . ? C9 C14 H14 119.6 . . ? C16 C15 C8 113.6(3) . . ? C16 C15 S1 105.1(2) . . ? C8 C15 S1 112.3(3) . . ? C16 C15 H15 108.6 . . ? C8 C15 H15 108.6 . . ? S1 C15 H15 108.6 . . ? C17 C16 C21 118.1(4) . . ? C17 C16 C15 120.2(4) . . ? C21 C16 C15 121.7(4) . . ? C18 C17 C16 122.1(4) . . ? C18 C17 H17 118.9 . . ? C16 C17 H17 118.9 . . ? C17 C18 C19 119.0(5) . . ? C17 C18 H18 120.5 . . ? C19 C18 H18 120.5 . . ? C20 C19 C18 119.8(4) . . ? C20 C19 H19 120.1 . . ? C18 C19 H19 120.1 . . ? C19 C20 C21 121.5(5) . . ? C19 C20 H20 119.3 . . ? C21 C20 H20 119.3 . . ? C20 C21 C16 119.5(5) . . ? C20 C21 H21 120.3 . . ? C16 C21 H21 120.3 . . ? C27 C22 C23 119.4(4) . . ? C27 C22 S1 120.4(3) . . ? C23 C22 S1 120.1(3) . . ? C24 C23 C22 119.0(5) . . ? C24 C23 H23 120.5 . . ? C22 C23 H23 120.5 . . ? C25 C24 C23 122.1(5) . . ? C25 C24 H24 119.0 . . ? C23 C24 H24 119.0 . . ? C24 C25 C26 118.4(5) . . ? C24 C25 C28 122.4(7) . . ? C26 C25 C28 119.2(7) . . ? C27 C26 C25 121.7(5) . . ? C27 C26 H26 119.2 . . ? C25 C26 H26 119.2 . . ? C26 C27 C22 119.3(5) . . ? C26 C27 H27 120.4 . . ? C22 C27 H27 120.4 . . ? C25 C28 H28A 109.5 . . ? C25 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C25 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C7 N1 C8 118.1(4) . . ? C4 O1 H1 115(5) . . ? O2 S1 C22 107.1(2) . . ? O2 S1 C15 107.19(18) . . ? C22 S1 C15 100.46(18) . . ? 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 C6 C1 C2 C3 -0.3(6) . . . . ? Cl1 C1 C2 C3 178.1(3) . . . . ? C1 C2 C3 C4 -1.0(6) . . . . ? C2 C3 C4 O1 -178.2(4) . . . . ? C2 C3 C4 C5 1.4(6) . . . . ? O1 C4 C5 C6 179.0(4) . . . . ? C3 C4 C5 C6 -0.5(5) . . . . ? O1 C4 C5 C7 1.4(6) . . . . ? C3 C4 C5 C7 -178.2(4) . . . . ? C2 C1 C6 C5 1.1(6) . . . . ? Cl1 C1 C6 C5 -177.3(3) . . . . ? C4 C5 C6 C1 -0.7(6) . . . . ? C7 C5 C6 C1 177.0(3) . . . . ? C6 C5 C7 N1 179.5(4) . . . . ? C4 C5 C7 N1 -2.8(6) . . . . ? N1 C8 C9 C10 71.7(4) . . . . ? C15 C8 C9 C10 -48.5(5) . . . . ? N1 C8 C9 C14 -105.0(4) . . . . ? C15 C8 C9 C14 134.8(4) . . . . ? C14 C9 C10 C11 -0.9(6) . . . . ? C8 C9 C10 C11 -177.6(4) . . . . ? C9 C10 C11 C12 1.0(7) . . . . ? C10 C11 C12 C13 -0.9(7) . . . . ? C11 C12 C13 C14 0.8(8) . . . . ? C12 C13 C14 C9 -0.7(7) . . . . ? C10 C9 C14 C13 0.7(6) . . . . ? C8 C9 C14 C13 177.6(4) . . . . ? N1 C8 C15 C16 46.6(4) . . . . ? C9 C8 C15 C16 166.8(3) . . . . ? N1 C8 C15 S1 165.7(3) . . . . ? C9 C8 C15 S1 -74.1(4) . . . . ? C8 C15 C16 C17 -131.6(4) . . . . ? S1 C15 C16 C17 105.3(4) . . . . ? C8 C15 C16 C21 48.5(5) . . . . ? S1 C15 C16 C21 -74.5(4) . . . . ? C21 C16 C17 C18 1.8(6) . . . . ? C15 C16 C17 C18 -178.1(4) . . . . ? C16 C17 C18 C19 -2.2(7) . . . . ? C17 C18 C19 C20 2.3(8) . . . . ? C18 C19 C20 C21 -2.1(8) . . . . ? C19 C20 C21 C16 1.7(7) . . . . ? C17 C16 C21 C20 -1.5(6) . . . . ? C15 C16 C21 C20 178.4(4) . . . . ? C27 C22 C23 C24 2.7(6) . . . . ? S1 C22 C23 C24 -179.3(4) . . . . ? C22 C23 C24 C25 0.6(7) . . . . ? C23 C24 C25 C26 -3.4(8) . . . . ? C23 C24 C25 C28 174.5(5) . . . . ? C24 C25 C26 C27 3.1(7) . . . . ? C28 C25 C26 C27 -174.8(5) . . . . ? C25 C26 C27 C22 0.1(7) . . . . ? C23 C22 C27 C26 -2.9(6) . . . . ? S1 C22 C27 C26 179.0(3) . . . . ? C5 C7 N1 C8 179.2(3) . . . . ? C9 C8 N1 C7 94.3(4) . . . . ? C15 C8 N1 C7 -140.4(3) . . . . ? C27 C22 S1 O2 0.6(4) . . . . ? C23 C22 S1 O2 -177.4(3) . . . . ? C27 C22 S1 C15 -111.2(3) . . . . ? C23 C22 S1 C15 70.8(3) . . . . ? C16 C15 S1 O2 86.1(3) . . . . ? C8 C15 S1 O2 -37.8(3) . . . . ? C16 C15 S1 C22 -162.1(3) . . . . ? C8 C15 S1 C22 74.0(3) . . . . ? 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 O1 H1 N1 0.82(2) 1.96(5) 2.627(5) 138(6) . _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 23.98 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.178 _refine_diff_density_min -0.244 _refine_diff_density_rms 0.041