# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2001 # CCDC Number:188/283 # CCDC ELECTRONIC DATA DEPOSITION FORM (CIF, VERSION DEC95) # This electronic data deposition form must be associated with CIF # output and can be used : # (a) WHEN SUBMITTING A PAPER TO A JOURNAL FOR PUBLICATION or # (b) WHEN SUBMITTING A PRIVATE COMMUNICATION TO THE CCDC # A comprehensive archive of CIF resources is maintained by the IUCr # at its Chester office. This can be accessed # by anonymous ftp to ftp.iucr.ac.uk # or via the WWW at http://www.iucr.ac.uk/cif/home.html # If data items in this form are not available or not applicable # then ignore these items # A few items specific to CCDC input are indicated by _ccdc_ # Submission and help information is provided at the end of this form #------------------------------------------------------------------------- #1 Data block identification for start of deposition data_j1725 #------------------------------------------------------------------------- #2 Person making the deposition _publ_contact_author 'Veronika Harmat' _publ_contact_author_email veronika@para.chem.elte.hu #------------------------------------------------------------------------- #3 Publication details # Provide these details if the structure has been published, # accepted or submitted for publication # The CCDC journal deposition number, eg. 182/357, # should be included only if it has been assigned by the journal loop_ _publ_author_name 'Pe\'ter Nagy' 'Antal Csa\'mpai' 'De\'nes Szabo\'' 'Jeno\" Varga' 'Veronika Harmat' 'Ferenc Ruff' 'A\'rpa\'d Kucsman' _journal_name_full 'J. Chem. Soc., Perkin Trans. II' _journal_volume '?' _journal_page_first '?' _journal_page_last '?' _journal_year '?' _ccdc_journal_depnumber '?' #------------------------------------------------------------------------- #4 Chemical and physical data # Note that the units for melting point are Kelvin # The compound_id is the identifier for the compound in the published # paper, eg. 4a, II, etc. # Provide a brief description of any significant biological activity, # eg. antimalarial activity # If the compound exhibits polymorphism provide brief details, # eg. monoclinic form, low-temperature phase, etc. # For chemdiag include any ASCII file output by a chemical drawing # package # Against _type record, for example, ChemDraw # Against _records supply the chemical connectivity records _chemical_name_systematic '?' _chemical_name_common '?' _chemical_formula_moiety '?' _chemical_formula_sum 'C15 H16 Cl N O3 S' _chemical_formula_weight 325.80 _chemical_melting_point ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_compound_source ? _ccdc_compound_id '?' _ccdc_biological_activity '?' _ccdc_polymorph '?' _ccdc_chemdiag_type '?' _loop _ccdc_chemdiag_records ? _exptl_crystal_density_diffrn 1.373 _exptl_crystal_colour transparent #------------------------------------------------------------------------- #5 Other data relating to the structure determination and refinement # Record the radiation type if not X-rays, eg. neutron # Record the temperature of the data collection (Kelvin) # if not room-temperature # Record R_squared if this is the only reliability factor given by # your refinement program # Describe briefly any disorder, eg. t-Butyl C31-33 disordered over # two sites with occupancies 0.6 and 0.4 # Under ccdc_comments record any other important information _diffrn_radiation_type MoK\a _diffrn_measurement_device 'RAXIS II' _ccdc_temp_data_collection 293(2) _ccdc_ls_R_squared ? _refine_ls_abs_structure_details '?' _ccdc_disorder '?' _ccdc_comments '?' #------------------------------------------------------------------------- #6 Include your "standard" CIF file here # It should contain the following data items: # unit cell parameters and volume, z value, space group symbol, # R-factor(s), atomic coordinates with standard deviations, # occupancy factors, bond lengths and bond angles # Other data items may be present but will not necessarily be # included in the Cambridge Structural Database # Do not include structure factors  #------------------------------------------------------------------------- #SUBMISSION INFORMATION # For a journal send the form to the address specified by the journal # For a private communication to the CCDC send the form to the address # deposit@chemcrys.cam.ac.uk # If you have any problems with the form please contact the CCDC # Technical Editors : # by e-mail: teched@chemcrys.cam.ac.uk # by telephone: +44 1223 336031/2 _audit_creation_method SHELXL loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'Cl' 'Cl' 0.1484 0.1585 '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' 'O' 'O' 0.0106 0.0060 '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' '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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.162(4) _cell_length_b 10.872(4) _cell_length_c 8.234(2) _cell_angle_alpha 104.94(3) _cell_angle_beta 93.172(13) _cell_angle_gamma 63.989(11) _cell_volume 788.2(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0.00 _cell_measurement_theta_max 0.00 _exptl_crystal_description ; ENTER NAME ENTER ADDRESS ; _exptl_crystal_size_max 0.500 _exptl_crystal_size_mid 0.400 _exptl_crystal_size_min 0.200 _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_F_000 340 _exptl_absorpt_coefficient_mu 0.383 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_method 'omega scans with profile analysis' _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.00 _diffrn_reflns_number 1688 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0917 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.23 _diffrn_reflns_theta_max 22.52 _reflns_number_total 1688 _reflns_number_observed 1277 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'teXsan: PROCESS (MSC)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material 'teXsan: FINISH (MSC)' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 1 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.1497P)^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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.2105(376) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 1687 _refine_ls_number_parameters 196 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0948 _refine_ls_R_factor_obs 0.0676 _refine_ls_wR_factor_all 0.2578 _refine_ls_wR_factor_obs 0.1931 _refine_ls_goodness_of_fit_all 1.188 _refine_ls_goodness_of_fit_obs 1.062 _refine_ls_restrained_S_all 1.216 _refine_ls_restrained_S_obs 1.062 _refine_ls_shift/esd_max 0.012 _refine_ls_shift/esd_mean 0.001 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Cl1 Cl 0.14622(15) 0.74078(15) 0.2458(2) 0.1031(9) Uani 1 d . . S1 S 0.31730(13) 0.39305(14) 0.2992(2) 0.0872(8) Uani 1 d . . O1 O 0.3846(4) 0.5029(4) 0.3200(6) 0.1007(13) Uani 1 d . . H1O H 0.3348(56) 0.5645(52) 0.2726(94) 0.178(39) Uiso 1 calc R . O2 O 0.2147(4) 0.2271(4) 0.2732(5) 0.0962(13) Uani 1 d . . O3 O 0.4545(4) 0.2207(5) -0.0117(5) 0.1057(14) Uani 1 d . . N1 N 0.0496(5) 0.2178(5) 0.4308(7) 0.0965(15) Uani 1 d . . H1N H 0.0041(5) 0.2453(5) 0.5279(7) 0.085(17) Uiso 1 calc R . C1 C 0.2570(5) 0.4268(5) 0.5106(7) 0.081(2) Uani 1 d . . C2 C 0.1710(5) 0.3655(5) 0.5471(7) 0.085(2) Uani 1 d . . C3 C 0.1183(6) 0.4037(6) 0.7111(8) 0.098(2) Uani 1 d . . H3 H 0.0589(6) 0.3660(6) 0.7386(8) 0.107(7) Uiso 1 calc R . C4 C 0.1501(7) 0.4959(7) 0.8362(8) 0.110(2) Uani 1 d . . H4 H 0.1138(7) 0.5187(7) 0.9466(8) 0.107(7) Uiso 1 calc R . C5 C 0.2355(6) 0.5538(7) 0.7973(9) 0.112(2) Uani 1 d . . H5 H 0.2582(6) 0.6152(7) 0.8823(9) 0.107(7) Uiso 1 calc R . C6 C 0.2883(5) 0.5227(6) 0.6351(9) 0.095(2) Uani 1 d . . H6 H 0.3438(5) 0.5647(6) 0.6085(9) 0.107(7) Uiso 1 calc R . C7 C 0.1455(6) 0.2635(5) 0.4086(8) 0.085(2) Uani 1 d . . C8 C 0.0192(7) 0.1208(6) 0.2925(9) 0.117(2) Uani 1 d . . H8A H -0.0532(7) 0.0987(6) 0.3311(9) 0.160(13) Uiso 1 calc R . H8B H 0.1078(7) 0.0353(6) 0.2538(9) 0.160(13) Uiso 1 calc R . H8C H -0.0168(7) 0.1647(6) 0.2017(9) 0.160(13) Uiso 1 calc R . C1' C 0.4847(5) 0.2361(5) 0.2729(8) 0.082(2) Uani 1 d . . C2' C 0.5359(6) 0.1647(6) 0.1101(8) 0.088(2) Uani 1 d . . C3' C 0.6667(6) 0.0413(6) 0.0759(9) 0.099(2) Uani 1 d . . H3' H 0.7034(6) -0.0099(6) -0.0341(9) 0.107(7) Uiso 1 calc R . C4' C 0.7399(6) -0.0019(7) 0.2114(10) 0.106(2) Uani 1 d . . H4' H 0.8275(6) -0.0845(7) 0.1910(10) 0.107(7) Uiso 1 calc R . C5' C 0.6899(6) 0.0705(7) 0.3736(9) 0.104(2) Uani 1 d . . H5' H 0.7428(6) 0.0379(7) 0.4619(9) 0.107(7) Uiso 1 calc R . C6' C 0.5609(6) 0.1918(6) 0.4056(8) 0.095(2) Uani 1 d . . H6' H 0.5255(6) 0.2435(6) 0.5159(8) 0.107(7) Uiso 1 calc R . C9 C 0.5135(7) 0.1610(8) -0.1791(8) 0.122(2) Uani 1 d . . H9A H 0.4446(7) 0.2106(8) -0.2513(8) 0.160(13) Uiso 1 calc R . H9B H 0.5331(7) 0.0629(8) -0.2122(8) 0.160(13) Uiso 1 calc R . H9C H 0.6031(7) 0.1688(8) -0.1884(8) 0.160(13) Uiso 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 Cl1 0.1010(13) 0.0837(12) 0.113(2) 0.0177(9) 0.0123(9) -0.0323(8) S1 0.0799(12) 0.0808(12) 0.0928(14) 0.0154(9) 0.0043(8) -0.0309(8) O1 0.095(2) 0.097(3) 0.115(3) 0.028(3) 0.000(2) -0.045(2) O2 0.095(2) 0.095(3) 0.086(3) -0.003(2) 0.014(2) -0.043(2) O3 0.095(3) 0.112(3) 0.084(3) 0.021(3) 0.010(2) -0.024(2) N1 0.089(3) 0.085(3) 0.109(4) 0.008(3) 0.022(3) -0.038(2) C1 0.078(3) 0.066(3) 0.085(4) 0.005(3) 0.009(3) -0.025(2) C2 0.080(3) 0.069(3) 0.092(4) 0.007(3) 0.014(3) -0.025(3) C3 0.093(4) 0.089(4) 0.101(5) 0.012(4) 0.012(3) -0.036(3) C4 0.106(4) 0.122(5) 0.079(5) -0.003(4) 0.015(3) -0.044(4) C5 0.095(4) 0.109(5) 0.105(6) -0.015(4) -0.001(4) -0.043(4) C6 0.087(4) 0.084(4) 0.098(5) -0.001(3) 0.012(3) -0.035(3) C7 0.081(3) 0.064(3) 0.092(4) 0.002(3) 0.010(3) -0.023(3) C8 0.111(4) 0.088(4) 0.140(6) -0.010(4) 0.013(4) -0.053(3) C1' 0.075(3) 0.080(3) 0.081(4) 0.016(3) 0.014(3) -0.025(2) C2' 0.080(3) 0.086(4) 0.096(5) 0.025(4) 0.002(3) -0.033(3) C3' 0.084(4) 0.092(4) 0.098(5) 0.009(4) 0.012(3) -0.026(3) C4' 0.079(4) 0.085(4) 0.134(7) 0.019(4) 0.008(4) -0.021(3) C5' 0.094(4) 0.094(4) 0.106(5) 0.033(4) 0.000(4) -0.022(3) C6' 0.094(4) 0.100(4) 0.077(4) 0.017(3) 0.004(3) -0.031(3) C9 0.113(5) 0.151(6) 0.081(5) 0.021(4) 0.018(4) -0.042(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 O1 1.587(4) . ? S1 C1 1.770(6) . ? S1 C1' 1.777(5) . ? O2 C7 1.229(6) . ? O3 C2' 1.357(7) . ? O3 C9 1.403(7) . ? N1 C7 1.312(7) . ? N1 C8 1.460(7) . ? C1 C6 1.393(7) . ? C1 C2 1.394(7) . ? C2 C3 1.370(8) . ? C2 C7 1.471(7) . ? C3 C4 1.373(8) . ? C4 C5 1.366(9) . ? C5 C6 1.368(9) . ? C1' C2' 1.363(8) . ? C1' C6' 1.370(8) . ? C2' C3' 1.389(8) . ? C3' C4' 1.375(8) . ? C4' C5' 1.358(8) . ? C5' C6' 1.367(8) . ? 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 O1 S1 C1 100.4(2) . . ? O1 S1 C1' 98.1(2) . . ? C1 S1 C1' 102.8(3) . . ? C2' O3 C9 118.4(4) . . ? C7 N1 C8 120.8(6) . . ? C6 C1 C2 121.6(5) . . ? C6 C1 S1 118.7(4) . . ? C2 C1 S1 119.6(4) . . ? C3 C2 C1 117.0(5) . . ? C3 C2 C7 125.0(5) . . ? C1 C2 C7 118.0(5) . . ? C2 C3 C4 122.3(6) . . ? C5 C4 C3 119.5(6) . . ? C6 C5 C4 121.0(6) . . ? C5 C6 C1 118.6(6) . . ? O2 C7 N1 122.6(5) . . ? O2 C7 C2 117.1(5) . . ? N1 C7 C2 120.3(6) . . ? C2' C1' C6' 121.8(5) . . ? C2' C1' S1 115.2(4) . . ? C6' C1' S1 123.0(4) . . ? O3 C2' C1' 117.0(5) . . ? O3 C2' C3' 123.3(6) . . ? C1' C2' C3' 119.7(6) . . ? C4' C3' C2' 117.2(6) . . ? C5' C4' C3' 123.0(6) . . ? C4' C5' C6' 119.2(6) . . ? C5' C6' C1' 119.0(6) . . ? 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 O1 S1 C1 C6 -4.4(5) . . . . ? C1' S1 C1 C6 96.5(4) . . . . ? O1 S1 C1 C2 171.0(4) . . . . ? C1' S1 C1 C2 -88.1(4) . . . . ? C6 C1 C2 C3 0.0(8) . . . . ? S1 C1 C2 C3 -175.2(4) . . . . ? C6 C1 C2 C7 -179.0(5) . . . . ? S1 C1 C2 C7 5.8(6) . . . . ? C1 C2 C3 C4 -1.3(8) . . . . ? C7 C2 C3 C4 177.6(5) . . . . ? C2 C3 C4 C5 0.9(10) . . . . ? C3 C4 C5 C6 0.8(10) . . . . ? C4 C5 C6 C1 -2.1(9) . . . . ? C2 C1 C6 C5 1.6(8) . . . . ? S1 C1 C6 C5 176.9(4) . . . . ? C8 N1 C7 O2 -0.5(8) . . . . ? C8 N1 C7 C2 177.6(5) . . . . ? C3 C2 C7 O2 -171.3(5) . . . . ? C1 C2 C7 O2 7.7(7) . . . . ? C3 C2 C7 N1 10.4(9) . . . . ? C1 C2 C7 N1 -170.6(5) . . . . ? O1 S1 C1' C2' -94.1(4) . . . . ? C1 S1 C1' C2' 163.3(4) . . . . ? O1 S1 C1' C6' 83.4(5) . . . . ? C1 S1 C1' C6' -19.2(5) . . . . ? C9 O3 C2' C1' 171.5(5) . . . . ? C9 O3 C2' C3' -7.8(8) . . . . ? C6' C1' C2' O3 -177.5(5) . . . . ? S1 C1' C2' O3 0.0(7) . . . . ? C6' C1' C2' C3' 1.8(8) . . . . ? S1 C1' C2' C3' 179.4(4) . . . . ? O3 C2' C3' C4' 178.5(5) . . . . ? C1' C2' C3' C4' -0.7(8) . . . . ? C2' C3' C4' C5' -0.3(9) . . . . ? C3' C4' C5' C6' 0.2(10) . . . . ? C4' C5' C6' C1' 0.8(9) . . . . ? C2' C1' C6' C5' -1.8(9) . . . . ? S1 C1' C6' C5' -179.2(4) . . . . ? _refine_diff_density_max 0.287 _refine_diff_density_min -0.327 _refine_diff_density_rms 0.072