# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Huimin Ma' 'Wen Shi' _publ_contact_author_name 'Huimin Ma' _publ_contact_author_address ; Institute of Chemistry, Chinese Academy of Sciences, Beijing 100080, China Beijing 100080 CHINA ; _publ_contact_author_email MAHM@ICCAS.AC.CN _publ_requested_journal 'Chemical Communications' _publ_section_title ; Rhodamine B thiolactone: a simple chemosensor for Hg2+ in aqueous media ; data_2078 _database_code_depnum_ccdc_archive 'CCDC 667970' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H30 N2 O2 S' _chemical_formula_sum 'C28 H30 N2 O2 S' _chemical_formula_weight 458.60 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pna2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z+1/2' _cell_length_a 16.441(3) _cell_length_b 12.319(3) _cell_length_c 12.173(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2465.4(9) _cell_formula_units_Z 4 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 28702 _cell_measurement_theta_min 1.2 _cell_measurement_theta_max 27.4 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.236 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 976 _exptl_absorpt_coefficient_mu 0.158 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.9630 _exptl_absorpt_correction_T_max 0.9720 _exptl_absorpt_process_details 'ABSCOR by T.Higashi 8 March, 1995' _exptl_special_details ; ? ; _diffrn_ambient_temperature 294(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID IP' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.00 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5295 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.1749 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.07 _diffrn_reflns_theta_max 27.41 _reflns_number_total 5295 _reflns_number_gt 2128 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Rapid Auto(Rigaku 2001)' _computing_cell_refinement 'Rapid Auto(Rigaku 2001)' _computing_data_reduction 'Rapid Auto(Rigaku 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0505P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _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 0.54(14) _refine_ls_number_reflns 5295 _refine_ls_number_parameters 303 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1378 _refine_ls_R_factor_gt 0.0468 _refine_ls_wR_factor_ref 0.1401 _refine_ls_wR_factor_gt 0.0905 _refine_ls_goodness_of_fit_ref 0.782 _refine_ls_restrained_S_all 0.782 _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 S1 S 0.01847(7) 0.68148(9) -0.07198(12) 0.0545(3) Uani 1 1 d . . . O1 O 0.0339(3) 0.8294(3) -0.2282(3) 0.0859(13) Uani 1 1 d . . . O2 O 0.0757(2) 0.4215(2) 0.1179(3) 0.0511(9) Uani 1 1 d . . . N1 N 0.1822(2) 0.6239(3) 0.4150(4) 0.0576(11) Uani 1 1 d . . . N2 N 0.0270(3) 0.1517(3) -0.1551(4) 0.0620(13) Uani 1 1 d . . . C1 C 0.0674(4) 0.7611(4) -0.1744(5) 0.0602(15) Uani 1 1 d . . . C2 C 0.1542(3) 0.7300(3) -0.1789(4) 0.0456(13) Uani 1 1 d . . . C3 C 0.2134(4) 0.7821(4) -0.2426(4) 0.0669(16) Uani 1 1 d . . . H3 H 0.1998 0.8424 -0.2848 0.080 Uiso 1 1 calc R . . C4 C 0.2914(4) 0.7439(5) -0.2424(5) 0.0741(18) Uani 1 1 d . . . H4 H 0.3303 0.7775 -0.2862 0.089 Uiso 1 1 calc R . . C5 C 0.3136(4) 0.6563(5) -0.1784(6) 0.0750(18) Uani 1 1 d . . . H5 H 0.3672 0.6319 -0.1788 0.090 Uiso 1 1 calc R . . C6 C 0.2564(3) 0.6049(4) -0.1139(5) 0.0609(15) Uani 1 1 d . . . H6 H 0.2711 0.5455 -0.0711 0.073 Uiso 1 1 calc R . . C7 C 0.1768(3) 0.6425(3) -0.1134(4) 0.0451(12) Uani 1 1 d . . . C8 C 0.1111(3) 0.5925(3) -0.0418(4) 0.0444(12) Uani 1 1 d . . . C9 C 0.1313(3) 0.6008(3) 0.0789(4) 0.0425(12) Uani 1 1 d . . . C10 C 0.1124(3) 0.5170(3) 0.1498(4) 0.0401(11) Uani 1 1 d . . . C11 C 0.1281(3) 0.5249(4) 0.2605(4) 0.0451(12) Uani 1 1 d . . . H11 H 0.1129 0.4683 0.3067 0.054 Uiso 1 1 calc R . . C12 C 0.1663(3) 0.6161(4) 0.3050(4) 0.0481(12) Uani 1 1 d . . . C13 C 0.1875(3) 0.7006(4) 0.2321(4) 0.0550(13) Uani 1 1 d . . . H13 H 0.2135 0.7624 0.2585 0.066 Uiso 1 1 calc R . . C14 C 0.1700(3) 0.6918(4) 0.1229(5) 0.0554(13) Uani 1 1 d . . . H14 H 0.1843 0.7484 0.0762 0.066 Uiso 1 1 calc R . . C15 C 0.0911(2) 0.4761(3) -0.0714(4) 0.0415(10) Uani 1 1 d . . . C16 C 0.0743(3) 0.3974(3) 0.0069(4) 0.0402(12) Uani 1 1 d . . . C17 C 0.0534(3) 0.2904(4) -0.0185(5) 0.0467(13) Uani 1 1 d . . . H17 H 0.0432 0.2410 0.0377 0.056 Uiso 1 1 calc R . . C18 C 0.0479(3) 0.2577(4) -0.1259(4) 0.0478(13) Uani 1 1 d . . . C19 C 0.0638(3) 0.3355(4) -0.2073(4) 0.0541(14) Uani 1 1 d . . . H19 H 0.0607 0.3164 -0.2811 0.065 Uiso 1 1 calc R . . C20 C 0.0841(3) 0.4404(4) -0.1780(5) 0.0573(15) Uani 1 1 d . . . H20 H 0.0937 0.4901 -0.2341 0.069 Uiso 1 1 calc R . . C21 C 0.2285(3) 0.7166(4) 0.4599(4) 0.0631(15) Uani 1 1 d . . . H21A H 0.2719 0.7349 0.4092 0.076 Uiso 1 1 calc R . . H21B H 0.2533 0.6948 0.5288 0.076 Uiso 1 1 calc R . . C22 C 0.1772(4) 0.8164(4) 0.4797(5) 0.0830(18) Uani 1 1 d . . . H22A H 0.1533 0.8396 0.4116 0.124 Uiso 1 1 calc R . . H22B H 0.2107 0.8734 0.5086 0.124 Uiso 1 1 calc R . . H22C H 0.1349 0.7996 0.5313 0.124 Uiso 1 1 calc R . . C23 C 0.1430(3) 0.5531(4) 0.4945(4) 0.0633(16) Uani 1 1 d . . . H23A H 0.0911 0.5297 0.4649 0.076 Uiso 1 1 calc R . . H23B H 0.1321 0.5944 0.5608 0.076 Uiso 1 1 calc R . . C24 C 0.1931(4) 0.4528(5) 0.5248(5) 0.0768(18) Uani 1 1 d . . . H24A H 0.2119 0.4179 0.4590 0.115 Uiso 1 1 calc R . . H24B H 0.1599 0.4032 0.5658 0.115 Uiso 1 1 calc R . . H24C H 0.2389 0.4743 0.5686 0.115 Uiso 1 1 calc R . . C25 C 0.0192(4) 0.1183(4) -0.2687(5) 0.0789(18) Uani 1 1 d . . . H25A H -0.0094 0.1749 -0.3085 0.095 Uiso 1 1 calc R . . H25B H -0.0144 0.0536 -0.2713 0.095 Uiso 1 1 calc R . . C26 C 0.0968(4) 0.0953(5) -0.3267(6) 0.100(2) Uani 1 1 d . . . H26A H 0.1306 0.1588 -0.3251 0.150 Uiso 1 1 calc R . . H26B H 0.0856 0.0759 -0.4015 0.150 Uiso 1 1 calc R . . H26C H 0.1243 0.0364 -0.2908 0.150 Uiso 1 1 calc R . . C27 C 0.0167(3) 0.0660(3) -0.0695(6) 0.0719(16) Uani 1 1 d . . . H27A H -0.0161 0.0076 -0.0996 0.086 Uiso 1 1 calc R . . H27B H -0.0126 0.0965 -0.0076 0.086 Uiso 1 1 calc R . . C28 C 0.0955(4) 0.0204(5) -0.0298(6) 0.094(2) Uani 1 1 d . . . H28A H 0.1305 0.0069 -0.0913 0.140 Uiso 1 1 calc R . . H28B H 0.0856 -0.0464 0.0086 0.140 Uiso 1 1 calc R . . H28C H 0.1210 0.0713 0.0190 0.140 Uiso 1 1 calc R . . 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 0.0526(7) 0.0407(6) 0.0703(8) 0.0056(8) -0.0014(8) 0.0064(6) O1 0.110(3) 0.057(2) 0.091(3) 0.028(2) -0.023(3) 0.016(2) O2 0.068(2) 0.0367(18) 0.049(2) 0.0040(15) -0.0047(17) -0.0156(17) N1 0.070(3) 0.057(3) 0.046(3) 0.001(2) -0.004(2) -0.015(2) N2 0.083(4) 0.037(2) 0.066(3) -0.005(2) -0.008(3) -0.005(2) C1 0.079(4) 0.035(3) 0.066(4) -0.002(3) -0.014(3) -0.006(3) C2 0.070(4) 0.029(3) 0.038(3) -0.004(2) -0.002(3) -0.013(2) C3 0.112(5) 0.038(3) 0.051(3) 0.003(3) 0.002(4) -0.020(3) C4 0.092(5) 0.064(4) 0.066(4) -0.010(3) 0.036(4) -0.028(4) C5 0.064(4) 0.067(4) 0.094(5) -0.004(4) 0.018(4) -0.013(3) C6 0.053(3) 0.051(3) 0.079(4) 0.011(3) 0.005(3) -0.001(3) C7 0.056(3) 0.036(3) 0.044(3) -0.002(2) 0.002(2) -0.007(2) C8 0.043(3) 0.031(2) 0.060(4) 0.008(2) -0.002(2) 0.008(2) C9 0.048(3) 0.033(2) 0.046(3) 0.006(2) -0.001(2) 0.001(2) C10 0.035(3) 0.034(3) 0.051(3) -0.001(2) 0.001(2) -0.001(2) C11 0.050(3) 0.037(3) 0.049(3) 0.006(2) 0.010(3) -0.004(2) C12 0.048(3) 0.047(3) 0.049(3) 0.003(3) 0.007(3) 0.002(2) C13 0.061(3) 0.047(3) 0.057(4) -0.002(3) 0.000(3) -0.010(3) C14 0.066(3) 0.034(3) 0.066(4) 0.009(3) 0.001(3) -0.015(3) C15 0.043(3) 0.043(2) 0.039(3) 0.000(3) -0.008(3) 0.006(2) C16 0.040(3) 0.034(2) 0.047(3) 0.004(2) -0.008(2) 0.001(2) C17 0.048(3) 0.034(3) 0.058(3) 0.005(2) -0.003(3) 0.001(2) C18 0.048(3) 0.035(3) 0.060(4) -0.001(3) -0.001(3) 0.003(2) C19 0.069(4) 0.044(3) 0.050(3) -0.008(3) -0.002(3) -0.001(3) C20 0.069(4) 0.044(3) 0.059(4) 0.016(3) 0.002(3) -0.007(3) C21 0.061(4) 0.077(4) 0.051(4) 0.004(3) -0.013(3) -0.006(3) C22 0.104(5) 0.070(4) 0.075(4) -0.008(4) -0.014(4) 0.005(4) C23 0.065(4) 0.075(4) 0.050(4) -0.011(3) 0.009(3) -0.001(3) C24 0.081(4) 0.077(4) 0.073(4) 0.017(3) 0.006(4) 0.005(3) C25 0.101(5) 0.050(3) 0.086(5) -0.012(3) -0.004(4) -0.020(3) C26 0.118(6) 0.081(5) 0.100(6) -0.019(4) 0.010(5) 0.014(4) C27 0.066(3) 0.048(3) 0.101(5) -0.014(4) -0.012(4) -0.009(3) C28 0.085(5) 0.070(4) 0.126(6) -0.003(4) -0.014(4) -0.002(4) _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 1.779(6) . ? S1 C8 1.912(4) . ? O1 C1 1.200(6) . ? O2 C10 1.379(5) . ? O2 C16 1.384(6) . ? N1 C12 1.367(7) . ? N1 C23 1.453(6) . ? N1 C21 1.477(6) . ? N2 C18 1.396(6) . ? N2 C25 1.449(7) . ? N2 C27 1.493(7) . ? C1 C2 1.478(7) . ? C2 C7 1.392(6) . ? C2 C3 1.401(7) . ? C3 C4 1.366(7) . ? C3 H3 0.9300 . ? C4 C5 1.380(8) . ? C4 H4 0.9300 . ? C5 C6 1.379(7) . ? C5 H5 0.9300 . ? C6 C7 1.388(7) . ? C6 H6 0.9300 . ? C7 C8 1.518(6) . ? C8 C9 1.510(7) . ? C8 C15 1.515(6) . ? C9 C10 1.380(6) . ? C9 C14 1.395(6) . ? C10 C11 1.376(6) . ? C11 C12 1.397(6) . ? C11 H11 0.9300 . ? C12 C13 1.412(6) . ? C13 C14 1.365(7) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C15 C20 1.376(7) . ? C15 C16 1.387(6) . ? C16 C17 1.397(6) . ? C17 C18 1.371(7) . ? C17 H17 0.9300 . ? C18 C19 1.402(7) . ? C19 C20 1.381(6) . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? C21 C22 1.510(6) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 C24 1.531(7) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C25 C26 1.486(8) . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? C27 C28 1.493(7) . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? 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 C8 95.2(2) . . ? C10 O2 C16 117.7(4) . . ? C12 N1 C23 121.7(4) . . ? C12 N1 C21 121.0(4) . . ? C23 N1 C21 116.5(4) . . ? C18 N2 C25 122.0(4) . . ? C18 N2 C27 120.8(4) . . ? C25 N2 C27 117.1(4) . . ? O1 C1 C2 127.2(5) . . ? O1 C1 S1 124.1(5) . . ? C2 C1 S1 108.6(4) . . ? C7 C2 C3 119.1(5) . . ? C7 C2 C1 116.0(4) . . ? C3 C2 C1 124.9(5) . . ? C4 C3 C2 119.5(5) . . ? C4 C3 H3 120.2 . . ? C2 C3 H3 120.2 . . ? C3 C4 C5 121.3(6) . . ? C3 C4 H4 119.3 . . ? C5 C4 H4 119.3 . . ? C6 C5 C4 120.0(6) . . ? C6 C5 H5 120.0 . . ? C4 C5 H5 120.0 . . ? C5 C6 C7 119.5(5) . . ? C5 C6 H6 120.2 . . ? C7 C6 H6 120.2 . . ? C6 C7 C2 120.5(4) . . ? C6 C7 C8 122.6(4) . . ? C2 C7 C8 116.9(4) . . ? C9 C8 C15 110.0(4) . . ? C9 C8 C7 112.0(4) . . ? C15 C8 C7 113.7(4) . . ? C9 C8 S1 108.9(3) . . ? C15 C8 S1 108.9(3) . . ? C7 C8 S1 103.0(3) . . ? C10 C9 C14 117.6(5) . . ? C10 C9 C8 120.5(4) . . ? C14 C9 C8 121.9(4) . . ? C11 C10 O2 114.7(4) . . ? C11 C10 C9 121.1(4) . . ? O2 C10 C9 124.1(5) . . ? C10 C11 C12 121.4(4) . . ? C10 C11 H11 119.3 . . ? C12 C11 H11 119.3 . . ? N1 C12 C11 121.5(4) . . ? N1 C12 C13 121.1(5) . . ? C11 C12 C13 117.4(5) . . ? C14 C13 C12 120.1(5) . . ? C14 C13 H13 120.0 . . ? C12 C13 H13 120.0 . . ? C13 C14 C9 122.3(5) . . ? C13 C14 H14 118.8 . . ? C9 C14 H14 118.8 . . ? C20 C15 C16 114.1(4) . . ? C20 C15 C8 123.0(4) . . ? C16 C15 C8 122.8(4) . . ? O2 C16 C15 121.2(4) . . ? O2 C16 C17 115.0(4) . . ? C15 C16 C17 123.8(4) . . ? C18 C17 C16 120.2(5) . . ? C18 C17 H17 119.9 . . ? C16 C17 H17 119.9 . . ? C17 C18 N2 122.2(5) . . ? C17 C18 C19 117.5(4) . . ? N2 C18 C19 120.3(5) . . ? C20 C19 C18 120.1(5) . . ? C20 C19 H19 119.9 . . ? C18 C19 H19 119.9 . . ? C15 C20 C19 124.2(5) . . ? C15 C20 H20 117.9 . . ? C19 C20 H20 117.9 . . ? N1 C21 C22 113.6(4) . . ? N1 C21 H21A 108.8 . . ? C22 C21 H21A 108.8 . . ? N1 C21 H21B 108.8 . . ? C22 C21 H21B 108.8 . . ? H21A C21 H21B 107.7 . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? N1 C23 C24 113.9(4) . . ? N1 C23 H23A 108.8 . . ? C24 C23 H23A 108.8 . . ? N1 C23 H23B 108.8 . . ? C24 C23 H23B 108.8 . . ? H23A C23 H23B 107.7 . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? N2 C25 C26 115.5(6) . . ? N2 C25 H25A 108.4 . . ? C26 C25 H25A 108.4 . . ? N2 C25 H25B 108.4 . . ? C26 C25 H25B 108.4 . . ? H25A C25 H25B 107.5 . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? N2 C27 C28 113.2(5) . . ? N2 C27 H27A 108.9 . . ? C28 C27 H27A 108.9 . . ? N2 C27 H27B 108.9 . . ? C28 C27 H27B 108.9 . . ? H27A C27 H27B 107.8 . . ? C27 C28 H28A 109.5 . . ? C27 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C27 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? 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 C8 S1 C1 O1 175.5(5) . . . . ? C8 S1 C1 C2 -5.6(3) . . . . ? O1 C1 C2 C7 -175.5(5) . . . . ? S1 C1 C2 C7 5.7(5) . . . . ? O1 C1 C2 C3 4.9(8) . . . . ? S1 C1 C2 C3 -173.9(4) . . . . ? C7 C2 C3 C4 2.3(7) . . . . ? C1 C2 C3 C4 -178.1(5) . . . . ? C2 C3 C4 C5 -1.6(9) . . . . ? C3 C4 C5 C6 0.7(9) . . . . ? C4 C5 C6 C7 -0.5(9) . . . . ? C5 C6 C7 C2 1.3(7) . . . . ? C5 C6 C7 C8 -178.0(5) . . . . ? C3 C2 C7 C6 -2.2(7) . . . . ? C1 C2 C7 C6 178.2(4) . . . . ? C3 C2 C7 C8 177.1(4) . . . . ? C1 C2 C7 C8 -2.5(6) . . . . ? C6 C7 C8 C9 60.8(6) . . . . ? C2 C7 C8 C9 -118.5(4) . . . . ? C6 C7 C8 C15 -64.7(6) . . . . ? C2 C7 C8 C15 116.0(4) . . . . ? C6 C7 C8 S1 177.6(4) . . . . ? C2 C7 C8 S1 -1.7(5) . . . . ? C1 S1 C8 C9 123.2(3) . . . . ? C1 S1 C8 C15 -116.8(4) . . . . ? C1 S1 C8 C7 4.2(3) . . . . ? C15 C8 C9 C10 -14.7(6) . . . . ? C7 C8 C9 C10 -142.2(4) . . . . ? S1 C8 C9 C10 104.6(4) . . . . ? C15 C8 C9 C14 164.7(4) . . . . ? C7 C8 C9 C14 37.2(6) . . . . ? S1 C8 C9 C14 -76.0(5) . . . . ? C16 O2 C10 C11 -166.1(4) . . . . ? C16 O2 C10 C9 15.2(6) . . . . ? C14 C9 C10 C11 2.6(7) . . . . ? C8 C9 C10 C11 -177.9(4) . . . . ? C14 C9 C10 O2 -178.7(4) . . . . ? C8 C9 C10 O2 0.7(7) . . . . ? O2 C10 C11 C12 178.9(4) . . . . ? C9 C10 C11 C12 -2.3(7) . . . . ? C23 N1 C12 C11 -16.0(7) . . . . ? C21 N1 C12 C11 175.0(4) . . . . ? C23 N1 C12 C13 163.7(5) . . . . ? C21 N1 C12 C13 -5.3(7) . . . . ? C10 C11 C12 N1 -179.8(4) . . . . ? C10 C11 C12 C13 0.6(7) . . . . ? N1 C12 C13 C14 -179.0(5) . . . . ? C11 C12 C13 C14 0.6(7) . . . . ? C12 C13 C14 C9 -0.2(8) . . . . ? C10 C9 C14 C13 -1.4(7) . . . . ? C8 C9 C14 C13 179.2(5) . . . . ? C9 C8 C15 C20 -168.4(4) . . . . ? C7 C8 C15 C20 -41.9(6) . . . . ? S1 C8 C15 C20 72.3(5) . . . . ? C9 C8 C15 C16 14.8(6) . . . . ? C7 C8 C15 C16 141.4(4) . . . . ? S1 C8 C15 C16 -104.4(4) . . . . ? C10 O2 C16 C15 -15.0(6) . . . . ? C10 O2 C16 C17 166.2(4) . . . . ? C20 C15 C16 O2 -177.6(4) . . . . ? C8 C15 C16 O2 -0.6(6) . . . . ? C20 C15 C16 C17 1.1(6) . . . . ? C8 C15 C16 C17 178.1(4) . . . . ? O2 C16 C17 C18 178.2(5) . . . . ? C15 C16 C17 C18 -0.5(8) . . . . ? C16 C17 C18 N2 -179.8(4) . . . . ? C16 C17 C18 C19 0.0(8) . . . . ? C25 N2 C18 C17 178.4(6) . . . . ? C27 N2 C18 C17 -5.4(8) . . . . ? C25 N2 C18 C19 -1.4(8) . . . . ? C27 N2 C18 C19 174.9(5) . . . . ? C17 C18 C19 C20 0.0(8) . . . . ? N2 C18 C19 C20 179.7(5) . . . . ? C16 C15 C20 C19 -1.2(7) . . . . ? C8 C15 C20 C19 -178.2(5) . . . . ? C18 C19 C20 C15 0.7(8) . . . . ? C12 N1 C21 C22 82.6(6) . . . . ? C23 N1 C21 C22 -86.9(6) . . . . ? C12 N1 C23 C24 95.1(6) . . . . ? C21 N1 C23 C24 -95.4(6) . . . . ? C18 N2 C25 C26 79.4(7) . . . . ? C27 N2 C25 C26 -97.0(6) . . . . ? C18 N2 C27 C28 -79.4(6) . . . . ? C25 N2 C27 C28 97.1(6) . . . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 27.41 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.254 _refine_diff_density_min -0.267 _refine_diff_density_rms 0.089