# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_mo_sb_jh_216_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H21 N3 S2' _chemical_formula_sum 'C24 H21 N3 S2' _chemical_formula_weight 415.58 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 Monoclinic _symmetry_space_group_name_H-M P2(1) _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 6.2365(19) _cell_length_b 8.196(3) _cell_length_c 20.593(7) _cell_angle_alpha 90.00 _cell_angle_beta 92.844(9) _cell_angle_gamma 90.00 _cell_volume 1051.3(6) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1141 _cell_measurement_theta_min 2.68 _cell_measurement_theta_max 19.20 _exptl_crystal_description flake _exptl_crystal_colour colourless _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.313 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 436 _exptl_absorpt_coefficient_mu 0.269 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.969 _exptl_absorpt_correction_T_max 0.993 _exptl_absorpt_process_details 'SADABS; BRUKER, 2008' _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 8516 _diffrn_reflns_av_R_equivalents 0.0518 _diffrn_reflns_av_sigmaI/netI 0.0740 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 0.99 _diffrn_reflns_theta_max 25.02 _reflns_number_total 3698 _reflns_number_gt 2647 _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^)+(0.0261P)^2^+0.2164P] 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 0.00(9) _refine_ls_number_reflns 3698 _refine_ls_number_parameters 262 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0745 _refine_ls_R_factor_gt 0.0446 _refine_ls_wR_factor_ref 0.0942 _refine_ls_wR_factor_gt 0.0779 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_restrained_S_all 1.002 _refine_ls_shift/su_max 0.001 _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 N1 N -0.1288(5) 0.8643(4) 0.55576(17) 0.0617(10) Uani 1 1 d . . . N2 N -0.1103(5) 0.3432(4) 0.67968(17) 0.0592(10) Uani 1 1 d . . . N3 N -0.1677(4) 0.6804(3) 0.68035(13) 0.0349(7) Uani 1 1 d . . . S1 S -0.02060(14) 0.70818(12) 0.80129(5) 0.0453(3) Uani 1 1 d . . . S2 S -0.46105(14) 0.81483(13) 0.75285(5) 0.0493(3) Uani 1 1 d . . . C1 C -0.1125(8) 1.0050(7) 0.5229(2) 0.0828(16) Uani 1 1 d . . . H1 H 0.0141 1.0242 0.5021 0.099 Uiso 1 1 calc R . . C2 C -0.2672(8) 1.1208(6) 0.5178(2) 0.0784(15) Uani 1 1 d . . . H2 H -0.2468 1.2158 0.4942 0.094 Uiso 1 1 calc R . . C3 C -0.4545(8) 1.0948(6) 0.5483(2) 0.0727(14) Uani 1 1 d . . . H3 H -0.5645 1.1715 0.5458 0.087 Uiso 1 1 calc R . . C4 C -0.4762(6) 0.9507(5) 0.5833(2) 0.0547(11) Uani 1 1 d . . . H4 H -0.6015 0.9293 0.6045 0.066 Uiso 1 1 calc R . . C5 C -0.3095(5) 0.8405(5) 0.58601(17) 0.0423(9) Uani 1 1 d . . . C6 C -0.3218(5) 0.6823(5) 0.62376(17) 0.0415(9) Uani 1 1 d . . . H6A H -0.4661 0.6685 0.6384 0.050 Uiso 1 1 calc R . . H6B H -0.2917 0.5915 0.5954 0.050 Uiso 1 1 calc R . . C7 C -0.0886(7) 0.1831(5) 0.6927(2) 0.0677(13) Uani 1 1 d . . . H7 H -0.2109 0.1180 0.6897 0.081 Uiso 1 1 calc R . . C8 C 0.1026(7) 0.1107(5) 0.7102(2) 0.0649(13) Uani 1 1 d . . . H8 H 0.1097 -0.0006 0.7187 0.078 Uiso 1 1 calc R . . C9 C 0.2811(7) 0.2036(6) 0.7148(3) 0.0776(15) Uani 1 1 d . . . H9 H 0.4136 0.1578 0.7268 0.093 Uiso 1 1 calc R . . C10 C 0.2631(6) 0.3689(5) 0.7013(2) 0.0615(13) Uani 1 1 d . . . H10 H 0.3840 0.4354 0.7038 0.074 Uiso 1 1 calc R . . C11 C 0.0663(5) 0.4330(4) 0.68433(17) 0.0358(9) Uani 1 1 d . . . C12 C 0.0465(5) 0.6123(4) 0.66888(18) 0.0389(9) Uani 1 1 d . . . H12A H 0.1535 0.6715 0.6953 0.047 Uiso 1 1 calc R . . H12B H 0.0773 0.6291 0.6237 0.047 Uiso 1 1 calc R . . C13 C -0.2233(5) 0.7331(4) 0.73872(18) 0.0370(9) Uani 1 1 d . . . C14 C -0.1285(6) 0.8175(6) 0.86868(17) 0.0551(11) Uani 1 1 d . . . H14A H -0.1928 0.9190 0.8533 0.066 Uiso 1 1 calc R . . H14B H -0.2392 0.7525 0.8877 0.066 Uiso 1 1 calc R . . C15 C 0.0484(5) 0.8532(5) 0.91953(18) 0.0445(10) Uani 1 1 d . . . C16 C 0.2316(6) 0.9432(5) 0.9020(2) 0.0507(11) Uani 1 1 d . . . H16 H 0.2447 0.9751 0.8591 0.061 Uiso 1 1 calc R . . C17 C 0.3883(6) 0.9831(5) 0.9478(2) 0.0541(11) Uani 1 1 d . . . H17 H 0.5072 1.0419 0.9355 0.065 Uiso 1 1 calc R . . C18 C 0.3734(6) 0.9364(5) 1.0139(2) 0.0465(10) Uani 1 1 d . . . C19 C 0.5340(7) 0.9789(6) 1.0624(2) 0.0634(13) Uani 1 1 d . . . H19 H 0.6545 1.0372 1.0512 0.076 Uiso 1 1 calc R . . C20 C 0.5111(8) 0.9341(6) 1.1253(2) 0.0735(14) Uani 1 1 d . . . H20 H 0.6184 0.9601 1.1566 0.088 Uiso 1 1 calc R . . C21 C 0.3293(8) 0.8498(6) 1.1437(2) 0.0728(14) Uani 1 1 d . . . H21 H 0.3153 0.8221 1.1871 0.087 Uiso 1 1 calc R . . C22 C 0.1714(6) 0.8078(6) 1.09805(19) 0.0567(10) Uani 1 1 d . . . H22 H 0.0509 0.7518 1.1109 0.068 Uiso 1 1 calc R . . C23 C 0.1890(5) 0.8486(5) 1.03152(18) 0.0430(10) Uani 1 1 d . . . C24 C 0.0318(5) 0.8091(5) 0.98265(18) 0.0465(9) Uani 1 1 d . . . H24 H -0.0884 0.7505 0.9940 0.056 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 N1 0.053(2) 0.075(3) 0.059(2) 0.024(2) 0.0121(17) 0.0103(18) N2 0.048(2) 0.038(2) 0.091(3) -0.001(2) -0.0034(18) -0.0017(17) N3 0.0336(16) 0.0326(18) 0.0385(18) 0.0022(15) 0.0000(13) 0.0042(14) S1 0.0396(5) 0.0525(6) 0.0430(6) -0.0023(5) -0.0047(4) 0.0091(5) S2 0.0344(5) 0.0557(7) 0.0576(6) -0.0029(6) -0.0009(4) 0.0093(5) C1 0.070(4) 0.101(4) 0.079(4) 0.041(4) 0.011(3) 0.001(3) C2 0.087(4) 0.073(4) 0.074(4) 0.041(3) -0.006(3) 0.000(3) C3 0.081(4) 0.066(3) 0.070(3) 0.021(3) -0.008(3) 0.017(3) C4 0.050(3) 0.060(3) 0.054(3) 0.011(2) 0.000(2) 0.009(2) C5 0.043(2) 0.046(3) 0.037(2) 0.004(2) -0.0085(17) 0.005(2) C6 0.037(2) 0.043(3) 0.043(2) 0.000(2) -0.0063(17) -0.0032(18) C7 0.057(3) 0.041(3) 0.105(4) -0.002(3) 0.004(2) -0.012(2) C8 0.065(3) 0.037(3) 0.092(4) 0.005(3) -0.001(3) 0.005(2) C9 0.051(3) 0.047(3) 0.133(5) 0.017(3) -0.012(3) 0.012(3) C10 0.036(2) 0.042(3) 0.106(4) 0.008(2) -0.002(2) 0.0005(19) C11 0.039(2) 0.029(2) 0.040(2) 0.0009(17) 0.0014(17) 0.0017(17) C12 0.038(2) 0.037(2) 0.042(2) -0.0020(19) 0.0036(17) -0.0008(17) C13 0.0303(19) 0.032(2) 0.049(2) 0.0011(19) -0.0037(16) -0.0030(15) C14 0.046(2) 0.072(3) 0.047(2) -0.009(3) 0.0021(18) 0.008(2) C15 0.040(2) 0.054(3) 0.040(2) -0.006(2) 0.0026(17) 0.005(2) C16 0.053(3) 0.060(3) 0.040(2) 0.003(2) 0.009(2) -0.003(2) C17 0.048(3) 0.059(3) 0.056(3) -0.005(2) 0.008(2) -0.012(2) C18 0.045(2) 0.044(2) 0.050(3) -0.008(2) 0.003(2) 0.0040(19) C19 0.056(3) 0.073(4) 0.061(3) -0.017(3) -0.003(2) -0.010(2) C20 0.065(3) 0.086(4) 0.068(4) -0.017(3) -0.011(3) -0.001(3) C21 0.090(4) 0.086(4) 0.042(3) -0.006(3) -0.002(3) 0.003(3) C22 0.062(3) 0.057(3) 0.051(3) -0.002(3) 0.005(2) 0.000(2) C23 0.043(2) 0.043(3) 0.043(2) -0.006(2) 0.0038(18) 0.0023(19) C24 0.038(2) 0.050(2) 0.052(3) -0.003(2) 0.0067(18) -0.006(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 N1 C5 1.329(4) . ? N1 C1 1.344(6) . ? N2 C11 1.324(4) . ? N2 C7 1.345(5) . ? N3 C13 1.339(4) . ? N3 C6 1.473(4) . ? N3 C12 1.478(4) . ? S1 C13 1.772(3) . ? S1 C14 1.809(4) . ? S2 C13 1.666(3) . ? C1 C2 1.354(6) . ? C1 H1 0.9300 . ? C2 C3 1.371(6) . ? C2 H2 0.9300 . ? C3 C4 1.393(6) . ? C3 H3 0.9300 . ? C4 C5 1.376(5) . ? C4 H4 0.9300 . ? C5 C6 1.516(5) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.364(5) . ? C7 H7 0.9300 . ? C8 C9 1.348(6) . ? C8 H8 0.9300 . ? C9 C10 1.386(6) . ? C9 H9 0.9300 . ? C10 C11 1.365(5) . ? C10 H10 0.9300 . ? C11 C12 1.507(5) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C14 C15 1.512(5) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C24 1.358(5) . ? C15 C16 1.421(5) . ? C16 C17 1.364(5) . ? C16 H16 0.9300 . ? C17 C18 1.421(5) . ? C17 H17 0.9300 . ? C18 C23 1.418(5) . ? C18 C19 1.423(5) . ? C19 C20 1.360(6) . ? C19 H19 0.9300 . ? C20 C21 1.396(6) . ? C20 H20 0.9300 . ? C21 C22 1.371(6) . ? C21 H21 0.9300 . ? C22 C23 1.420(5) . ? C22 H22 0.9300 . ? C23 C24 1.408(5) . ? C24 H24 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 C5 N1 C1 116.7(4) . . ? C11 N2 C7 116.9(3) . . ? C13 N3 C6 121.3(3) . . ? C13 N3 C12 122.8(3) . . ? C6 N3 C12 115.9(3) . . ? C13 S1 C14 102.81(17) . . ? N1 C1 C2 124.6(4) . . ? N1 C1 H1 117.7 . . ? C2 C1 H1 117.7 . . ? C1 C2 C3 118.5(5) . . ? C1 C2 H2 120.8 . . ? C3 C2 H2 120.8 . . ? C2 C3 C4 118.4(4) . . ? C2 C3 H3 120.8 . . ? C4 C3 H3 120.8 . . ? C5 C4 C3 119.0(4) . . ? C5 C4 H4 120.5 . . ? C3 C4 H4 120.5 . . ? N1 C5 C4 122.8(4) . . ? N1 C5 C6 115.6(3) . . ? C4 C5 C6 121.7(3) . . ? N3 C6 C5 111.5(3) . . ? N3 C6 H6A 109.3 . . ? C5 C6 H6A 109.3 . . ? N3 C6 H6B 109.3 . . ? C5 C6 H6B 109.3 . . ? H6A C6 H6B 108.0 . . ? N2 C7 C8 123.7(4) . . ? N2 C7 H7 118.1 . . ? C8 C7 H7 118.1 . . ? C9 C8 C7 118.7(4) . . ? C9 C8 H8 120.6 . . ? C7 C8 H8 120.6 . . ? C8 C9 C10 118.7(4) . . ? C8 C9 H9 120.7 . . ? C10 C9 H9 120.7 . . ? C11 C10 C9 119.4(4) . . ? C11 C10 H10 120.3 . . ? C9 C10 H10 120.3 . . ? N2 C11 C10 122.6(3) . . ? N2 C11 C12 117.9(3) . . ? C10 C11 C12 119.5(3) . . ? N3 C12 C11 113.6(3) . . ? N3 C12 H12A 108.9 . . ? C11 C12 H12A 108.9 . . ? N3 C12 H12B 108.9 . . ? C11 C12 H12B 108.9 . . ? H12A C12 H12B 107.7 . . ? N3 C13 S2 124.0(3) . . ? N3 C13 S1 114.1(2) . . ? S2 C13 S1 121.9(2) . . ? C15 C14 S1 109.9(2) . . ? C15 C14 H14A 109.7 . . ? S1 C14 H14A 109.7 . . ? C15 C14 H14B 109.7 . . ? S1 C14 H14B 109.7 . . ? H14A C14 H14B 108.2 . . ? C24 C15 C16 118.8(3) . . ? C24 C15 C14 121.6(3) . . ? C16 C15 C14 119.5(4) . . ? C17 C16 C15 120.4(4) . . ? C17 C16 H16 119.8 . . ? C15 C16 H16 119.8 . . ? C16 C17 C18 121.2(4) . . ? C16 C17 H17 119.4 . . ? C18 C17 H17 119.4 . . ? C23 C18 C17 118.3(4) . . ? C23 C18 C19 119.7(4) . . ? C17 C18 C19 122.0(4) . . ? C20 C19 C18 120.0(4) . . ? C20 C19 H19 120.0 . . ? C18 C19 H19 120.0 . . ? C19 C20 C21 121.1(4) . . ? C19 C20 H20 119.4 . . ? C21 C20 H20 119.4 . . ? C22 C21 C20 120.2(4) . . ? C22 C21 H21 119.9 . . ? C20 C21 H21 119.9 . . ? C21 C22 C23 121.0(4) . . ? C21 C22 H22 119.5 . . ? C23 C22 H22 119.5 . . ? C24 C23 C18 118.6(3) . . ? C24 C23 C22 123.4(4) . . ? C18 C23 C22 118.0(4) . . ? C15 C24 C23 122.6(3) . . ? C15 C24 H24 118.7 . . ? C23 C24 H24 118.7 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.183 _refine_diff_density_min -0.178 _refine_diff_density_rms 0.042 _database_code_depnum_ccdc_archive 'CCDC 942550'