# 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_mz4 _database_code_depnum_ccdc_archive 'CCDC 902684' #TrackingRef 'mz4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H10 N2 O S5' _chemical_formula_weight 370.53 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 P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.1317(16) _cell_length_b 20.856(4) _cell_length_c 8.7162(17) _cell_angle_alpha 90.00 _cell_angle_beta 101.63(3) _cell_angle_gamma 90.00 _cell_volume 1447.9(5) _cell_formula_units_Z 4 _cell_measurement_temperature 108(2) _cell_measurement_reflns_used 5986 _cell_measurement_theta_min 1.9515 _cell_measurement_theta_max 31.3407 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.700 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 760 _exptl_absorpt_coefficient_mu 0.798 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_max 0.9545 _exptl_absorpt_correction_T_min 0.8010 _exptl_absorpt_process_details 'face indexed' _exptl_special_details ; ? ; _diffrn_ambient_temperature 108(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'Graphite Monochromator' _diffrn_measurement_device ; Saturn724 (2x2 bin mode) ; _diffrn_measurement_method dtprofit.ref _diffrn_detector_area_resol_mean 28.5714 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15450 _diffrn_reflns_av_R_equivalents 0.0326 _diffrn_reflns_av_sigmaI/netI 0.0253 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.74 _diffrn_reflns_theta_max 31.39 _reflns_number_total 4250 _reflns_number_gt 4112 _reflns_threshold_expression >2\s(I) _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_measurement_details ; scan: Number of images: 360 Slice: -110.0000 - 70.0000 Image width: 0.5000 Exp time: 20.0000 Rotation axis: Omega Omega: 0.0000 Kappa: 0.0000 Phi: 0.0000 XTD: 44.9941 2theta: -19.9523 scan: Number of images: 280 Slice: -75.0000 - 65.0000 Image width: 0.5000 Exp time: 20.0000 Rotation axis: Omega Omega: 0.0000 Kappa: 0.0000 Phi: 90.0000 XTD: 44.9941 2theta: -19.9523 scan: Number of images: 220 Slice: -55.0000 - 55.0000 Image width: 0.5000 Exp time: 20.0000 Rotation axis: Omega Omega: 0.0000 Kappa: 50.0000 Phi: 90.0000 XTD: 44.9941 2theta: -19.9523 ; _diffrn_measurement_device_details ; AFC12 (Right): Kappa 3 circle ; _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _iucr_refine_instructions_details ; TITL mz4 in P2(1)/n CELL 0.71073 8.1317 20.8565 8.7162 90.000 101.632 90.000 ZERR 4.00 0.0016 0.0042 0.0017 0.000 0.030 0.000 LATT 1 SYMM 1/2 - X, 1/2 + Y, 1/2 - Z SFAC C H N O S UNIT 52 40 8 4 20 MERG 2 PLAN -5 FMAP 2 SIZE 0.20 0.30 0.45 ACTA 50.00 L.S. 24 TEMP -165.00 WGHT 0.110300 1.376000 FVAR 6.80303 S1 5 0.254232 0.252273 0.417373 11.00000 0.02642 0.01489 = 0.02353 0.00149 0.00447 0.00226 S2 5 0.431859 0.285897 0.603086 11.00000 0.02336 0.01999 = 0.02645 -0.00250 0.00826 -0.00286 S3 5 0.294164 0.310439 0.768534 11.00000 0.02742 0.01941 = 0.03112 -0.00607 0.01114 -0.00231 S4 5 0.244745 0.224873 0.867076 11.00000 0.02830 0.02317 = 0.02326 -0.00424 0.00989 -0.00266 S5 5 0.055694 0.184275 0.701861 11.00000 0.02092 0.02085 = 0.02937 -0.00631 0.01182 -0.00131 O1 4 0.131900 0.027325 0.641260 11.00000 0.03258 0.01841 = 0.02000 -0.00276 0.01213 -0.00745 N1 3 0.256125 0.063751 0.441297 11.00000 0.01687 0.01683 = 0.01741 -0.00130 0.00646 0.00015 N2 3 0.417172 0.068631 0.183342 11.00000 0.02631 0.02179 = 0.01937 -0.00032 0.00925 -0.00087 C1 1 0.306272 0.005673 0.382334 11.00000 0.01590 0.01622 = 0.01638 -0.00228 0.00276 -0.00110 C2 1 0.283454 -0.054422 0.446741 11.00000 0.01974 0.01681 = 0.02380 0.00023 0.00441 -0.00098 AFIX 43 H2 2 0.229358 -0.057816 0.533363 11.00000 -1.20000 AFIX 0 C3 1 0.340751 -0.109009 0.382631 11.00000 0.02177 0.01560 = 0.02717 -0.00063 0.00287 -0.00130 AFIX 43 H3 2 0.326875 -0.149821 0.426733 11.00000 -1.20000 AFIX 0 C4 1 0.418974 -0.104501 0.253313 11.00000 0.02003 0.01935 = 0.02734 -0.00665 0.00285 0.00059 AFIX 43 H4 2 0.456679 -0.142162 0.209699 11.00000 -1.20000 AFIX 0 C5 1 0.440878 -0.045569 0.189999 11.00000 0.02068 0.02302 = 0.02333 -0.00513 0.00594 0.00055 AFIX 43 H5 2 0.494313 -0.042878 0.102821 11.00000 -1.20000 AFIX 0 C6 1 0.385608 0.010792 0.251965 11.00000 0.01958 0.01869 = 0.01636 -0.00204 0.00465 -0.00080 C7 1 0.373499 0.120808 0.245527 11.00000 0.02291 0.02008 = 0.02251 0.00162 0.00509 -0.00055 AFIX 43 H7 2 0.395729 0.160604 0.200731 11.00000 -1.20000 AFIX 0 C8 1 0.294236 0.121963 0.376913 11.00000 0.01835 0.01467 = 0.01989 -0.00032 0.00357 0.00071 C9 1 0.239159 0.171052 0.459776 11.00000 0.01965 0.01595 = 0.02099 0.00089 0.00475 0.00200 C10 1 0.164377 0.142980 0.578121 11.00000 0.01914 0.01841 = 0.02302 -0.00268 0.00661 -0.00117 C11 1 0.179076 0.076728 0.564982 11.00000 0.01943 0.01749 = 0.01671 -0.00158 0.00720 -0.00168 C12 1 0.118590 0.033731 0.803733 11.00000 0.02175 0.02554 = 0.01943 0.00102 0.00750 -0.00037 AFIX 23 H12A 2 0.011746 0.054884 0.812041 11.00000 -1.20000 H12B 2 0.213012 0.059421 0.862449 11.00000 -1.20000 AFIX 0 C13 1 0.124369 -0.033532 0.866682 11.00000 0.02820 0.02491 = 0.02351 0.00553 0.00526 0.00244 AFIX 137 H13A 2 0.025912 -0.057345 0.812103 11.00000 -1.50000 H13B 2 0.124232 -0.032268 0.979050 11.00000 -1.50000 H13C 2 0.226732 -0.054822 0.849922 11.00000 -1.50000 HKLF 4 REM mz4 in P2(1)/n REM R1 = 0.0444 for 4112 Fo > 4sig(Fo) and 0.0504 for all 4250 data REM 191 parameters refined using 0 restraints END WGHT 0.1103 1.3804 REM Highest difference peak 0.694, deepest hole -0.781, 1-sigma level 0.173 Q1 1 0.1100 0.1665 0.6149 11.00000 0.05 0.69 Q2 1 -0.0727 0.1743 0.6215 11.00000 0.05 0.69 Q3 1 0.1943 0.1571 0.5220 11.00000 0.05 0.68 Q4 1 0.3991 0.3264 0.8709 11.00000 0.05 0.66 Q5 1 0.5812 0.0042 0.1199 11.00000 0.05 0.61 ; _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^ > 2\s(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^)+(0.1103P)^2^+1.3760P] 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 4250 _refine_ls_number_parameters 191 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0504 _refine_ls_R_factor_gt 0.0444 _refine_ls_wR_factor_ref 0.1775 _refine_ls_wR_factor_gt 0.1434 _refine_ls_goodness_of_fit_ref 1.152 _refine_ls_restrained_S_all 1.152 _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 0.25423(7) 0.25227(3) 0.41737(7) 0.02169(17) Uani 1 1 d . . . S2 S 0.43186(7) 0.28590(3) 0.60309(7) 0.02282(16) Uani 1 1 d . . . S3 S 0.29416(8) 0.31044(3) 0.76853(8) 0.02525(17) Uani 1 1 d . . . S4 S 0.24475(8) 0.22487(3) 0.86708(7) 0.02425(17) Uani 1 1 d . . . S5 S 0.05569(7) 0.18427(3) 0.70186(8) 0.02277(17) Uani 1 1 d . . . O1 O 0.1319(2) 0.02732(8) 0.6413(2) 0.0227(3) Uani 1 1 d . . . N1 N 0.2561(2) 0.06375(9) 0.4413(2) 0.0166(3) Uani 1 1 d . . . N2 N 0.4172(3) 0.06863(10) 0.1833(2) 0.0218(4) Uani 1 1 d . . . C1 C 0.3063(3) 0.00567(10) 0.3823(2) 0.0162(4) Uani 1 1 d . . . C2 C 0.2835(3) -0.05442(11) 0.4467(3) 0.0201(4) Uani 1 1 d . . . H2 H 0.2294 -0.0578 0.5334 0.024 Uiso 1 1 calc R . . C3 C 0.3408(3) -0.10901(11) 0.3826(3) 0.0218(4) Uani 1 1 d . . . H3 H 0.3269 -0.1498 0.4267 0.026 Uiso 1 1 calc R . . C4 C 0.4190(3) -0.10450(12) 0.2533(3) 0.0225(4) Uani 1 1 d . . . H4 H 0.4567 -0.1422 0.2097 0.027 Uiso 1 1 calc R . . C5 C 0.4409(3) -0.04557(12) 0.1900(3) 0.0221(4) Uani 1 1 d . . . H5 H 0.4943 -0.0429 0.1028 0.027 Uiso 1 1 calc R . . C6 C 0.3856(3) 0.01079(11) 0.2520(3) 0.0181(4) Uani 1 1 d . . . C7 C 0.3735(3) 0.12081(12) 0.2455(3) 0.0218(4) Uani 1 1 d . . . H7 H 0.3957 0.1606 0.2007 0.026 Uiso 1 1 calc R . . C8 C 0.2942(3) 0.12196(10) 0.3769(3) 0.0177(4) Uani 1 1 d . . . C9 C 0.2392(3) 0.17105(11) 0.4598(3) 0.0188(4) Uani 1 1 d . . . C10 C 0.1644(3) 0.14298(11) 0.5781(3) 0.0199(4) Uani 1 1 d . . . C11 C 0.1791(3) 0.07673(11) 0.5650(3) 0.0174(4) Uani 1 1 d . . . C12 C 0.1186(3) 0.03373(12) 0.8037(3) 0.0218(4) Uani 1 1 d . . . H12A H 0.0117 0.0549 0.8120 0.026 Uiso 1 1 calc R . . H12B H 0.2130 0.0594 0.8624 0.026 Uiso 1 1 calc R . . C13 C 0.1244(3) -0.03353(13) 0.8667(3) 0.0255(5) Uani 1 1 d . . . H13A H 0.0259 -0.0573 0.8121 0.038 Uiso 1 1 calc R . . H13B H 0.1242 -0.0323 0.9790 0.038 Uiso 1 1 calc R . . H13C H 0.2267 -0.0548 0.8499 0.038 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 0.0264(3) 0.0149(3) 0.0235(3) 0.00149(19) 0.0045(2) 0.00226(18) S2 0.0234(3) 0.0200(3) 0.0265(3) -0.0025(2) 0.0083(2) -0.00286(19) S3 0.0274(3) 0.0194(3) 0.0311(3) -0.0061(2) 0.0111(2) -0.0023(2) S4 0.0283(3) 0.0232(3) 0.0233(3) -0.0042(2) 0.0099(2) -0.0027(2) S5 0.0209(3) 0.0209(3) 0.0294(3) -0.0063(2) 0.0118(2) -0.00131(18) O1 0.0326(9) 0.0184(8) 0.0200(8) -0.0028(6) 0.0121(6) -0.0074(6) N1 0.0169(8) 0.0168(8) 0.0174(8) -0.0013(6) 0.0065(6) 0.0002(6) N2 0.0263(9) 0.0218(9) 0.0194(9) -0.0003(7) 0.0093(7) -0.0009(7) C1 0.0159(8) 0.0162(9) 0.0164(9) -0.0023(7) 0.0028(7) -0.0011(7) C2 0.0197(9) 0.0168(9) 0.0238(10) 0.0002(8) 0.0044(8) -0.0010(7) C3 0.0218(10) 0.0156(9) 0.0272(11) -0.0006(8) 0.0029(8) -0.0013(7) C4 0.0200(9) 0.0194(10) 0.0273(11) -0.0067(8) 0.0028(8) 0.0006(8) C5 0.0207(9) 0.0230(11) 0.0233(10) -0.0051(8) 0.0059(8) 0.0006(8) C6 0.0196(9) 0.0187(10) 0.0164(9) -0.0020(7) 0.0046(7) -0.0008(7) C7 0.0229(10) 0.0201(10) 0.0225(10) 0.0016(8) 0.0051(8) -0.0005(8) C8 0.0184(9) 0.0147(9) 0.0199(10) -0.0003(7) 0.0036(7) 0.0007(7) C9 0.0196(9) 0.0160(9) 0.0210(10) 0.0009(8) 0.0048(7) 0.0020(7) C10 0.0191(9) 0.0184(10) 0.0230(10) -0.0027(8) 0.0066(7) -0.0012(7) C11 0.0194(9) 0.0175(9) 0.0167(9) -0.0016(7) 0.0072(7) -0.0017(7) C12 0.0217(9) 0.0255(11) 0.0194(10) 0.0010(8) 0.0075(8) -0.0004(8) C13 0.0282(11) 0.0249(11) 0.0235(11) 0.0055(9) 0.0053(9) 0.0024(9) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C9 1.743(2) . ? S1 S2 2.0629(10) . ? S2 S3 2.0607(10) . ? S3 S4 2.0550(10) . ? S4 S5 2.0643(10) . ? S5 C10 1.752(2) . ? O1 C11 1.324(3) . ? O1 C12 1.448(3) . ? N1 C11 1.379(3) . ? N1 C8 1.398(3) . ? N1 C1 1.408(3) . ? N2 C7 1.297(3) . ? N2 C6 1.393(3) . ? C1 C2 1.401(3) . ? C1 C6 1.419(3) . ? C2 C3 1.389(3) . ? C3 C4 1.405(4) . ? C4 C5 1.374(4) . ? C5 C6 1.405(3) . ? C7 C8 1.423(3) . ? C8 C9 1.379(3) . ? C9 C10 1.425(3) . ? C10 C11 1.394(3) . ? C12 C13 1.504(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 C9 S1 S2 103.42(8) . . ? S3 S2 S1 103.90(4) . . ? S4 S3 S2 104.86(4) . . ? S3 S4 S5 104.21(4) . . ? C10 S5 S4 103.53(8) . . ? C11 O1 C12 120.37(18) . . ? C11 N1 C8 108.41(18) . . ? C11 N1 C1 131.69(19) . . ? C8 N1 C1 119.78(18) . . ? C7 N2 C6 117.2(2) . . ? C2 C1 N1 123.5(2) . . ? C2 C1 C6 120.4(2) . . ? N1 C1 C6 116.07(19) . . ? C3 C2 C1 119.3(2) . . ? C2 C3 C4 120.7(2) . . ? C5 C4 C3 119.9(2) . . ? C4 C5 C6 121.1(2) . . ? N2 C6 C5 117.3(2) . . ? N2 C6 C1 124.2(2) . . ? C5 C6 C1 118.5(2) . . ? N2 C7 C8 123.9(2) . . ? C9 C8 N1 108.23(19) . . ? C9 C8 C7 133.0(2) . . ? N1 C8 C7 118.77(19) . . ? C8 C9 C10 107.8(2) . . ? C8 C9 S1 124.50(18) . . ? C10 C9 S1 127.69(18) . . ? C11 C10 C9 107.0(2) . . ? C11 C10 S5 126.88(18) . . ? C9 C10 S5 125.84(18) . . ? O1 C11 N1 117.59(19) . . ? O1 C11 C10 133.8(2) . . ? N1 C11 C10 108.60(19) . . ? O1 C12 C13 105.5(2) . . ? _diffrn_measured_fraction_theta_max 0.892 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.694 _refine_diff_density_min -0.781 _refine_diff_density_rms 0.173