# 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 'Fan Zhang' _publ_contact_author_email fan-zhang@sjtu.edu.cn loop_ _publ_author_name 'Yinque Liu' 'Fan Zhang' 'Chunyang He' 'Dongqing Wu' 'Xiaodong Zhuang' 'Minzhao Xue' 'Xinliang Feng' data_mo10306a _database_code_depnum_ccdc_archive 'CCDC 860020' #TrackingRef '- Compound 5a-CCDC860020.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H7 N2 S2' _chemical_formula_weight 255.33 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' 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 P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.6998(16) _cell_length_b 7.4627(10) _cell_length_c 12.8404(16) _cell_angle_alpha 90.00 _cell_angle_beta 114.132(2) _cell_angle_gamma 90.00 _cell_volume 1110.6(2) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1727 _cell_measurement_theta_min 3.24 _cell_measurement_theta_max 27.00 _exptl_crystal_description column _exptl_crystal_colour yellow _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.527 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 524 _exptl_absorpt_coefficient_mu 0.453 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9477 _exptl_absorpt_correction_T_max 0.9821 _exptl_absorpt_process_details sadabs _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_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6006 _diffrn_reflns_av_R_equivalents 0.0640 _diffrn_reflns_av_sigmaI/netI 0.0968 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 27.47 _reflns_number_total 2053 _reflns_number_gt 1082 _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, 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^)+(0.1511P)^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_number_reflns 2053 _refine_ls_number_parameters 154 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1361 _refine_ls_R_factor_gt 0.0773 _refine_ls_wR_factor_ref 0.2456 _refine_ls_wR_factor_gt 0.2114 _refine_ls_goodness_of_fit_ref 0.945 _refine_ls_restrained_S_all 0.945 _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 0.57367(12) 0.2566(2) 0.43601(14) 0.0494(5) Uani 1 1 d . . . S2 S 1.09117(16) 0.0945(2) 0.93849(13) 0.0594(6) Uani 1 1 d . . . N1 N 0.7983(3) 0.1916(6) 0.6108(3) 0.0346(9) Uani 1 1 d . . . N2 N 0.8985(3) 0.1758(6) 0.7102(3) 0.0327(9) Uani 1 1 d . . . C1 C 0.5026(5) 0.3351(10) 0.3008(6) 0.0572(16) Uani 1 1 d . . . H1A H 0.4262 0.3730 0.2709 0.069 Uiso 1 1 calc R . . C2 C 0.5688(5) 0.3363(8) 0.2419(5) 0.0516(14) Uani 1 1 d . . . H2A H 0.5437 0.3774 0.1672 0.062 Uiso 1 1 calc R . . C3 C 0.6815(4) 0.2684(7) 0.3058(5) 0.0391(11) Uani 1 1 d . . . H3A H 0.7384 0.2614 0.2780 0.047 Uiso 1 1 calc R . . C4 C 0.6969(4) 0.2136(6) 0.4139(4) 0.0316(10) Uani 1 1 d . . . C5 C 0.8012(4) 0.1599(6) 0.5097(4) 0.0276(9) Uani 1 1 d . . . C6 C 0.9970(4) 0.1339(6) 0.7065(4) 0.0293(10) Uani 1 1 d . . . C7 C 1.0023(4) 0.0698(5) 0.6014(4) 0.0247(9) Uani 1 1 d . . . C8 C 0.9002(4) 0.0818(5) 0.5005(4) 0.0271(9) Uani 1 1 d . . . C9 C 1.1007(4) -0.0131(6) 0.6013(4) 0.0274(9) Uani 1 1 d . . . H9A H 1.1667 -0.0228 0.6687 0.033 Uiso 1 1 calc R . . C10 C 1.0972(4) 0.1494(7) 0.8139(4) 0.0340(11) Uani 1 1 d . . . C11 C 1.2153(4) 0.2171(6) 0.8345(4) 0.0288(10) Uani 1 1 d . . . H11A H 1.2414 0.2490 0.7791 0.035 Uiso 1 1 calc R . . C12 C 1.2796(6) 0.2233(10) 0.9544(7) 0.069(2) Uani 1 1 d . . . H12A H 1.3531 0.2729 0.9879 0.083 Uiso 1 1 calc R . . C13 C 1.2272(6) 0.1535(9) 1.0143(5) 0.0625(19) Uani 1 1 d . . . H13B H 1.2635 0.1383 1.0930 0.075 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 0.0322(7) 0.0632(9) 0.0608(9) 0.0027(7) 0.0271(7) 0.0071(6) S2 0.0852(14) 0.0547(9) 0.0478(9) 0.0028(7) 0.0368(9) 0.0062(8) N1 0.035(2) 0.043(2) 0.035(2) -0.0011(17) 0.0240(19) 0.0042(17) N2 0.033(2) 0.039(2) 0.032(2) -0.0051(17) 0.0191(18) 0.0014(17) C1 0.033(3) 0.063(4) 0.061(4) -0.002(3) 0.004(3) 0.009(3) C2 0.046(3) 0.050(3) 0.047(3) 0.003(3) 0.007(3) 0.013(3) C3 0.037(3) 0.042(3) 0.040(3) -0.001(2) 0.017(2) 0.008(2) C4 0.028(2) 0.034(2) 0.035(2) -0.0009(18) 0.015(2) 0.0026(18) C5 0.029(2) 0.025(2) 0.034(2) -0.0030(17) 0.0177(19) -0.0019(17) C6 0.040(3) 0.027(2) 0.027(2) 0.0012(16) 0.020(2) 0.0054(18) C7 0.028(2) 0.026(2) 0.026(2) -0.0033(16) 0.0168(18) -0.0038(17) C8 0.031(2) 0.024(2) 0.031(2) -0.0022(17) 0.018(2) -0.0007(17) C9 0.030(2) 0.028(2) 0.027(2) -0.0016(17) 0.0146(19) -0.0004(17) C10 0.038(3) 0.033(2) 0.036(2) -0.0013(19) 0.021(2) 0.007(2) C11 0.021(2) 0.042(3) 0.0177(19) -0.0136(17) 0.0027(17) -0.0046(17) C12 0.047(4) 0.084(5) 0.065(5) -0.035(4) 0.012(3) 0.009(3) C13 0.086(5) 0.057(4) 0.028(3) -0.004(2) 0.007(3) 0.026(3) _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 1.700(7) . ? S1 C4 1.731(4) . ? S2 C13 1.659(8) . ? S2 C10 1.683(5) . ? N1 C5 1.335(6) . ? N1 N2 1.391(6) . ? N2 C6 1.310(6) . ? C1 C2 1.341(10) . ? C1 H1A 0.9300 . ? C2 C3 1.420(7) . ? C2 H2A 0.9300 . ? C3 C4 1.382(7) . ? C3 H3A 0.9300 . ? C4 C5 1.448(7) . ? C5 C8 1.434(6) . ? C6 C10 1.449(7) . ? C6 C7 1.459(6) . ? C7 C9 1.396(6) . ? C7 C8 1.412(7) . ? C8 C9 1.399(6) 3_756 ? C9 C8 1.399(6) 3_756 ? C9 H9A 0.9300 . ? C10 C11 1.501(6) . ? C11 C12 1.418(9) . ? C11 H11A 0.9300 . ? C12 C13 1.314(11) . ? C12 H12A 0.9300 . ? C13 H13B 0.9300 . ? 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 92.0(3) . . ? C13 S2 C10 93.0(3) . . ? C5 N1 N2 120.0(4) . . ? C6 N2 N1 121.1(4) . . ? C2 C1 S1 112.6(5) . . ? C2 C1 H1A 123.7 . . ? S1 C1 H1A 123.7 . . ? C1 C2 C3 112.8(6) . . ? C1 C2 H2A 123.6 . . ? C3 C2 H2A 123.6 . . ? C4 C3 C2 112.4(5) . . ? C4 C3 H3A 123.8 . . ? C2 C3 H3A 123.8 . . ? C3 C4 C5 129.8(4) . . ? C3 C4 S1 110.1(4) . . ? C5 C4 S1 119.1(3) . . ? N1 C5 C8 121.8(4) . . ? N1 C5 C4 113.4(4) . . ? C8 C5 C4 124.8(4) . . ? N2 C6 C10 115.2(4) . . ? N2 C6 C7 121.2(4) . . ? C10 C6 C7 123.5(4) . . ? C9 C7 C8 120.9(4) . . ? C9 C7 C6 121.8(4) . . ? C8 C7 C6 117.2(4) . . ? C9 C8 C7 119.2(4) 3_756 . ? C9 C8 C5 123.6(4) 3_756 . ? C7 C8 C5 117.2(4) . . ? C7 C9 C8 119.9(4) . 3_756 ? C7 C9 H9A 120.0 . . ? C8 C9 H9A 120.0 3_756 . ? C6 C10 C11 128.3(4) . . ? C6 C10 S2 121.5(4) . . ? C11 C10 S2 110.2(3) . . ? C12 C11 C10 107.0(5) . . ? C12 C11 H11A 126.5 . . ? C10 C11 H11A 126.5 . . ? C13 C12 C11 114.7(6) . . ? C13 C12 H12A 122.6 . . ? C11 C12 H12A 122.6 . . ? C12 C13 S2 114.6(5) . . ? C12 C13 H13B 122.7 . . ? S2 C13 H13B 122.7 . . ? _diffrn_measured_fraction_theta_max 0.805 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.805 _refine_diff_density_max 0.541 _refine_diff_density_min -0.471 _refine_diff_density_rms 0.097 # Attachment '- Compound 5c-CCDC860021.cif' data_z _database_code_depnum_ccdc_archive 'CCDC 860021' #TrackingRef '- Compound 5c-CCDC860021.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C50 H62 N4 S4' _chemical_formula_weight 847.28 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' 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 P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 6.3583(3) _cell_length_b 41.420(2) _cell_length_c 8.9592(5) _cell_angle_alpha 90.00 _cell_angle_beta 104.922(2) _cell_angle_gamma 90.00 _cell_volume 2280.0(2) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.234 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 908 _exptl_absorpt_coefficient_mu 0.247 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9032 _exptl_absorpt_correction_T_max 0.9476 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 26363 _diffrn_reflns_av_R_equivalents 0.0456 _diffrn_reflns_av_sigmaI/netI 0.0289 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -49 _diffrn_reflns_limit_k_max 49 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.97 _diffrn_reflns_theta_max 25.01 _reflns_number_total 4035 _reflns_number_gt 3533 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0331P)^2^+8.3390P] 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_number_reflns 4035 _refine_ls_number_parameters 262 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0890 _refine_ls_R_factor_gt 0.0794 _refine_ls_wR_factor_ref 0.1734 _refine_ls_wR_factor_gt 0.1683 _refine_ls_goodness_of_fit_ref 1.154 _refine_ls_restrained_S_all 1.155 _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 0.43218(17) -0.10261(3) -0.13626(13) 0.0320(3) Uani 1 1 d . . . S2 S 0.79120(15) 0.02805(2) 0.39091(11) 0.0254(3) Uani 1 1 d . . . N1 N 0.5021(5) -0.04823(8) 0.0838(4) 0.0251(7) Uani 1 1 d . . . N2 N 0.5697(5) -0.02214(8) 0.1779(4) 0.0252(7) Uani 1 1 d . . . C1 C 1.110(2) -0.2617(4) -0.074(2) 0.281(12) Uani 1 1 d U . . H1A H 1.1902 -0.2774 -0.1208 0.422 Uiso 1 1 calc R . . H1B H 1.0581 -0.2722 0.0072 0.422 Uiso 1 1 calc R . . H1C H 1.2071 -0.2438 -0.0302 0.422 Uiso 1 1 calc R . . C2 C 0.917(3) -0.2487(4) -0.1983(19) 0.228(8) Uani 1 1 d U . . H2A H 0.9692 -0.2373 -0.2788 0.274 Uiso 1 1 calc R . . H2B H 0.8235 -0.2669 -0.2480 0.274 Uiso 1 1 calc R . . C3 C 0.800(2) -0.2285(2) -0.1350(12) 0.163(6) Uani 1 1 d . . . H3A H 0.9011 -0.2123 -0.0737 0.195 Uiso 1 1 calc R . . H3B H 0.7384 -0.2409 -0.0621 0.195 Uiso 1 1 calc R . . C4 C 0.6083(12) -0.20978(15) -0.2488(8) 0.076(2) Uani 1 1 d . . . H4A H 0.6628 -0.1999 -0.3322 0.091 Uiso 1 1 calc R . . H4B H 0.4924 -0.2253 -0.2968 0.091 Uiso 1 1 calc R . . C5 C 0.5126(9) -0.18366(12) -0.1683(6) 0.0495(13) Uani 1 1 d . . . H5A H 0.6319 -0.1695 -0.1116 0.059 Uiso 1 1 calc R . . H5B H 0.4467 -0.1939 -0.0913 0.059 Uiso 1 1 calc R . . C6 C 0.3420(9) -0.16307(12) -0.2755(6) 0.0483(13) Uani 1 1 d . . . H6A H 0.4027 -0.1547 -0.3592 0.058 Uiso 1 1 calc R . . H6B H 0.2153 -0.1768 -0.3236 0.058 Uiso 1 1 calc R . . C7 C 0.2655(7) -0.13515(10) -0.1970(5) 0.0348(10) Uani 1 1 d . . . C8 C 0.0711(7) -0.13091(10) -0.1620(5) 0.0360(10) Uani 1 1 d . . . H8A H -0.0432 -0.1463 -0.1861 0.043 Uiso 1 1 calc R . . C9 C 0.0554(6) -0.10150(10) -0.0866(5) 0.0297(9) Uani 1 1 d . . . H9A H -0.0696 -0.0951 -0.0544 0.036 Uiso 1 1 calc R . . C10 C 0.2394(6) -0.08320(9) -0.0647(4) 0.0249(8) Uani 1 1 d . . . C11 C 0.2950(6) -0.05201(9) 0.0139(4) 0.0227(8) Uani 1 1 d . . . C12 C 0.1367(6) -0.02694(9) 0.0083(4) 0.0209(8) Uani 1 1 d . . . C13 C 0.2088(6) 0.00069(9) 0.1010(4) 0.0209(8) Uani 1 1 d . . . C14 C 0.4289(6) -0.00004(9) 0.1976(4) 0.0214(8) Uani 1 1 d . . . C15 C 0.5130(6) 0.02288(9) 0.3212(4) 0.0220(8) Uani 1 1 d . . . C16 C 0.4063(6) 0.03991(10) 0.4100(5) 0.0269(9) Uani 1 1 d . . . H16A H 0.2524 0.0399 0.3926 0.032 Uiso 1 1 calc R . . C17 C 0.5465(6) 0.05739(10) 0.5295(5) 0.0280(9) Uani 1 1 d . . . H17A H 0.4963 0.0705 0.6002 0.034 Uiso 1 1 calc R . . C18 C 0.7599(6) 0.05384(10) 0.5345(4) 0.0260(9) Uani 1 1 d . . . C19 C 0.9495(7) 0.07000(10) 0.6420(5) 0.0312(9) Uani 1 1 d . . . H19A H 1.0702 0.0543 0.6733 0.037 Uiso 1 1 calc R . . H19B H 0.9073 0.0768 0.7362 0.037 Uiso 1 1 calc R . . C20 C 1.0295(7) 0.09934(10) 0.5705(5) 0.0314(9) Uani 1 1 d . . . H20A H 0.9032 0.1132 0.5233 0.038 Uiso 1 1 calc R . . H20B H 1.0941 0.0920 0.4869 0.038 Uiso 1 1 calc R . . C21 C 1.1972(8) 0.11932(11) 0.6853(5) 0.0391(11) Uani 1 1 d . . . H21A H 1.1303 0.1280 0.7652 0.047 Uiso 1 1 calc R . . H21B H 1.3203 0.1053 0.7373 0.047 Uiso 1 1 calc R . . C22 C 1.2824(12) 0.14708(15) 0.6069(7) 0.0718(19) Uani 1 1 d . . . H22A H 1.3533 0.1380 0.5300 0.086 Uiso 1 1 calc R . . H22B H 1.1568 0.1601 0.5500 0.086 Uiso 1 1 calc R . . C23 C 1.4418(13) 0.1692(2) 0.7127(10) 0.095(3) Uani 1 1 d . . . H23A H 1.4536 0.1894 0.6569 0.114 Uiso 1 1 calc R . . H23B H 1.3847 0.1747 0.8023 0.114 Uiso 1 1 calc R . . C24 C 1.6414(14) 0.1562(2) 0.7644(10) 0.117(3) Uani 1 1 d . . . H24A H 1.7353 0.1713 0.8359 0.176 Uiso 1 1 calc R . . H24B H 1.7035 0.1521 0.6768 0.176 Uiso 1 1 calc R . . H24C H 1.6310 0.1359 0.8181 0.176 Uiso 1 1 calc R . . C25 C 0.0712(6) 0.02726(9) 0.0904(4) 0.0223(8) Uani 1 1 d . . . H25A H 0.1203 0.0458 0.1516 0.027 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 0.0284(6) 0.0316(6) 0.0368(6) -0.0016(5) 0.0101(4) 0.0053(4) S2 0.0155(5) 0.0343(5) 0.0246(5) -0.0007(4) 0.0017(4) 0.0006(4) N1 0.0216(17) 0.0265(18) 0.0243(17) -0.0017(14) 0.0007(13) 0.0023(13) N2 0.0212(17) 0.0269(18) 0.0264(17) 0.0001(14) 0.0045(13) 0.0012(13) C1 0.139(12) 0.30(2) 0.40(3) 0.19(2) 0.049(14) 0.109(14) C2 0.221(17) 0.259(18) 0.207(16) 0.081(14) 0.060(12) 0.116(15) C3 0.280(15) 0.107(7) 0.151(9) 0.067(6) 0.145(10) 0.143(9) C4 0.102(5) 0.051(4) 0.082(5) 0.003(3) 0.038(4) 0.029(4) C5 0.059(3) 0.041(3) 0.049(3) -0.001(2) 0.016(3) 0.012(2) C6 0.063(3) 0.039(3) 0.038(3) -0.008(2) 0.004(2) 0.009(2) C7 0.043(3) 0.032(2) 0.025(2) -0.0003(18) 0.0001(19) 0.0076(19) C8 0.036(2) 0.029(2) 0.038(2) 0.0003(19) 0.001(2) -0.0029(19) C9 0.022(2) 0.031(2) 0.036(2) 0.0030(18) 0.0058(17) 0.0016(17) C10 0.0207(19) 0.026(2) 0.026(2) 0.0048(16) 0.0036(16) 0.0040(16) C11 0.022(2) 0.025(2) 0.0202(19) 0.0073(15) 0.0045(15) 0.0022(15) C12 0.0193(19) 0.0234(19) 0.0204(18) 0.0042(15) 0.0054(15) 0.0013(15) C13 0.0172(18) 0.0266(19) 0.0192(18) 0.0038(15) 0.0051(14) 0.0000(15) C14 0.0168(18) 0.0240(19) 0.0231(19) 0.0054(15) 0.0044(15) 0.0004(15) C15 0.0156(18) 0.026(2) 0.0227(19) 0.0054(15) 0.0015(15) 0.0005(15) C16 0.0169(19) 0.036(2) 0.027(2) 0.0020(17) 0.0045(16) 0.0003(16) C17 0.026(2) 0.033(2) 0.024(2) -0.0008(17) 0.0054(17) 0.0034(17) C18 0.025(2) 0.031(2) 0.0197(19) 0.0028(16) 0.0028(16) -0.0007(17) C19 0.028(2) 0.036(2) 0.024(2) 0.0004(18) -0.0018(17) -0.0035(18) C20 0.033(2) 0.033(2) 0.027(2) -0.0021(18) 0.0062(18) -0.0049(18) C21 0.037(3) 0.044(3) 0.036(2) -0.011(2) 0.008(2) -0.008(2) C22 0.093(5) 0.065(4) 0.067(4) -0.021(3) 0.038(4) -0.045(4) C23 0.086(6) 0.097(6) 0.108(6) -0.041(5) 0.036(5) -0.049(5) C24 0.088(6) 0.161(9) 0.080(6) -0.040(6) -0.020(5) 0.015(6) C25 0.0191(19) 0.0255(19) 0.0214(19) 0.0005(15) 0.0040(15) 0.0006(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 C7 1.714(5) . ? S1 C10 1.722(4) . ? S2 C18 1.723(4) . ? S2 C15 1.731(4) . ? N1 C11 1.313(5) . ? N1 N2 1.370(4) . ? N2 C14 1.323(5) . ? C1 C2 1.527(17) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C3 1.338(16) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.577(11) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.512(7) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.513(7) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.498(6) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.363(7) . ? C8 C9 1.409(6) . ? C8 H8A 0.9500 . ? C9 C10 1.365(6) . ? C9 H9A 0.9500 . ? C10 C11 1.470(5) . ? C11 C12 1.438(5) . ? C12 C25 1.388(5) 3 ? C12 C13 1.419(5) . ? C13 C25 1.394(5) . ? C13 C14 1.444(5) . ? C14 C15 1.452(5) . ? C15 C16 1.367(5) . ? C16 C17 1.405(6) . ? C16 H16A 0.9500 . ? C17 C18 1.354(6) . ? C17 H17A 0.9500 . ? C18 C19 1.494(5) . ? C19 C20 1.521(6) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 C21 1.522(6) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 C22 1.518(7) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 C23 1.505(8) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 C24 1.345(10) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 C12 1.388(5) 3 ? C25 H25A 0.9500 . ? 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 C7 S1 C10 92.5(2) . . ? C18 S2 C15 92.42(19) . . ? C11 N1 N2 120.3(3) . . ? C14 N2 N1 120.8(3) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C3 C2 C1 110.0(15) . . ? C3 C2 H2A 109.7 . . ? C1 C2 H2A 109.7 . . ? C3 C2 H2B 109.7 . . ? C1 C2 H2B 109.7 . . ? H2A C2 H2B 108.2 . . ? C2 C3 C4 117.0(10) . . ? C2 C3 H3A 108.0 . . ? C4 C3 H3A 108.0 . . ? C2 C3 H3B 108.0 . . ? C4 C3 H3B 108.0 . . ? H3A C3 H3B 107.3 . . ? C5 C4 C3 112.5(6) . . ? C5 C4 H4A 109.1 . . ? C3 C4 H4A 109.1 . . ? C5 C4 H4B 109.1 . . ? C3 C4 H4B 109.1 . . ? H4A C4 H4B 107.8 . . ? C4 C5 C6 114.3(5) . . ? C4 C5 H5A 108.7 . . ? C6 C5 H5A 108.7 . . ? C4 C5 H5B 108.7 . . ? C6 C5 H5B 108.7 . . ? H5A C5 H5B 107.6 . . ? C7 C6 C5 113.8(4) . . ? C7 C6 H6A 108.8 . . ? C5 C6 H6A 108.8 . . ? C7 C6 H6B 108.8 . . ? C5 C6 H6B 108.8 . . ? H6A C6 H6B 107.7 . . ? C8 C7 C6 129.1(4) . . ? C8 C7 S1 110.4(3) . . ? C6 C7 S1 120.5(4) . . ? C7 C8 C9 113.7(4) . . ? C7 C8 H8A 123.2 . . ? C9 C8 H8A 123.2 . . ? C10 C9 C8 112.7(4) . . ? C10 C9 H9A 123.7 . . ? C8 C9 H9A 123.7 . . ? C9 C10 C11 130.4(4) . . ? C9 C10 S1 110.7(3) . . ? C11 C10 S1 118.8(3) . . ? N1 C11 C12 122.5(4) . . ? N1 C11 C10 114.9(3) . . ? C12 C11 C10 122.5(3) . . ? C25 C12 C13 119.5(3) 3 . ? C25 C12 C11 123.9(4) 3 . ? C13 C12 C11 116.3(3) . . ? C25 C13 C12 119.6(3) . . ? C25 C13 C14 123.5(3) . . ? C12 C13 C14 116.8(3) . . ? N2 C14 C13 121.3(3) . . ? N2 C14 C15 115.2(3) . . ? C13 C14 C15 123.6(3) . . ? C16 C15 C14 129.8(3) . . ? C16 C15 S2 109.9(3) . . ? C14 C15 S2 119.8(3) . . ? C15 C16 C17 113.4(3) . . ? C15 C16 H16A 123.3 . . ? C17 C16 H16A 123.3 . . ? C18 C17 C16 113.8(4) . . ? C18 C17 H17A 123.1 . . ? C16 C17 H17A 123.1 . . ? C17 C18 C19 127.5(4) . . ? C17 C18 S2 110.5(3) . . ? C19 C18 S2 122.0(3) . . ? C18 C19 C20 112.8(3) . . ? C18 C19 H19A 109.0 . . ? C20 C19 H19A 109.0 . . ? C18 C19 H19B 109.0 . . ? C20 C19 H19B 109.0 . . ? H19A C19 H19B 107.8 . . ? C19 C20 C21 113.7(4) . . ? C19 C20 H20A 108.8 . . ? C21 C20 H20A 108.8 . . ? C19 C20 H20B 108.8 . . ? C21 C20 H20B 108.8 . . ? H20A C20 H20B 107.7 . . ? C22 C21 C20 111.8(4) . . ? C22 C21 H21A 109.3 . . ? C20 C21 H21A 109.3 . . ? C22 C21 H21B 109.3 . . ? C20 C21 H21B 109.3 . . ? H21A C21 H21B 107.9 . . ? C23 C22 C21 115.6(6) . . ? C23 C22 H22A 108.4 . . ? C21 C22 H22A 108.4 . . ? C23 C22 H22B 108.4 . . ? C21 C22 H22B 108.4 . . ? H22A C22 H22B 107.5 . . ? C24 C23 C22 113.4(7) . . ? C24 C23 H23A 108.9 . . ? C22 C23 H23A 108.9 . . ? C24 C23 H23B 108.9 . . ? C22 C23 H23B 108.9 . . ? 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 . . ? C12 C25 C13 120.9(4) 3 . ? C12 C25 H25A 119.5 3 . ? C13 C25 H25A 119.5 . . ? 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 C11 N1 N2 C14 -1.3(5) . . . . ? C1 C2 C3 C4 173.4(11) . . . . ? C2 C3 C4 C5 -170.5(13) . . . . ? C3 C4 C5 C6 174.6(7) . . . . ? C4 C5 C6 C7 -173.9(5) . . . . ? C5 C6 C7 C8 -107.7(6) . . . . ? C5 C6 C7 S1 71.8(6) . . . . ? C10 S1 C7 C8 -0.3(3) . . . . ? C10 S1 C7 C6 -179.9(4) . . . . ? C6 C7 C8 C9 179.7(4) . . . . ? S1 C7 C8 C9 0.1(5) . . . . ? C7 C8 C9 C10 0.2(5) . . . . ? C8 C9 C10 C11 -177.0(4) . . . . ? C8 C9 C10 S1 -0.5(5) . . . . ? C7 S1 C10 C9 0.5(3) . . . . ? C7 S1 C10 C11 177.5(3) . . . . ? N2 N1 C11 C12 11.6(5) . . . . ? N2 N1 C11 C10 -171.3(3) . . . . ? C9 C10 C11 N1 146.9(4) . . . . ? S1 C10 C11 N1 -29.4(5) . . . . ? C9 C10 C11 C12 -36.0(6) . . . . ? S1 C10 C11 C12 147.7(3) . . . . ? N1 C11 C12 C25 165.6(4) . . . 3 ? C10 C11 C12 C25 -11.3(6) . . . 3 ? N1 C11 C12 C13 -8.7(5) . . . . ? C10 C11 C12 C13 174.4(3) . . . . ? C25 C12 C13 C25 -0.7(6) 3 . . . ? C11 C12 C13 C25 173.8(3) . . . . ? C25 C12 C13 C14 -178.1(3) 3 . . . ? C11 C12 C13 C14 -3.5(5) . . . . ? N1 N2 C14 C13 -11.3(5) . . . . ? N1 N2 C14 C15 168.9(3) . . . . ? C25 C13 C14 N2 -163.9(4) . . . . ? C12 C13 C14 N2 13.3(5) . . . . ? C25 C13 C14 C15 15.9(6) . . . . ? C12 C13 C14 C15 -166.9(3) . . . . ? N2 C14 C15 C16 -152.5(4) . . . . ? C13 C14 C15 C16 27.7(6) . . . . ? N2 C14 C15 S2 19.3(5) . . . . ? C13 C14 C15 S2 -160.5(3) . . . . ? C18 S2 C15 C16 -1.6(3) . . . . ? C18 S2 C15 C14 -174.9(3) . . . . ? C14 C15 C16 C17 173.9(4) . . . . ? S2 C15 C16 C17 1.4(4) . . . . ? C15 C16 C17 C18 -0.5(5) . . . . ? C16 C17 C18 C19 177.3(4) . . . . ? C16 C17 C18 S2 -0.8(5) . . . . ? C15 S2 C18 C17 1.3(3) . . . . ? C15 S2 C18 C19 -176.8(3) . . . . ? C17 C18 C19 C20 -98.2(5) . . . . ? S2 C18 C19 C20 79.7(4) . . . . ? C18 C19 C20 C21 170.5(4) . . . . ? C19 C20 C21 C22 176.4(5) . . . . ? C20 C21 C22 C23 177.3(6) . . . . ? C21 C22 C23 C24 75.0(10) . . . . ? C12 C13 C25 C12 0.7(6) . . . 3 ? C14 C13 C25 C12 177.9(3) . . . 3 ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.266 _refine_diff_density_min -0.662 _refine_diff_density_rms 0.077