# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2004 data_global _audit_creation_method SHELXL _journal_coden_Cambridge 182 _publ_contact_author_name 'Tomas Torroba' _publ_contact_author_address ; Tomas Torroba Departamento de Quimica Facultad de Ciencias Universidad de Burgos 09001 BURGOS SPAIN ; _publ_contact_author_phone +34-947-258086 _publ_contact_author_fax +34-947-258087 _publ_contact_author_email ttorroba@ubu.es loop_ _publ_author_name _publ_author_address 'Sonia Macho' ; Departamento de Quimica Facultad de Ciencias Universidad de Burgos 09001 BURGOS SPAIN ; 'Daniel Miguel' ; Quimica Inorganica Facultad de Ciencias Universidad de Valladolid 47071 Valladolid SPAIN ; 'Ana G. Neo' ; Departamento de Quimica Facultad de Ciencias Universidad de Burgos 09001 BURGOS SPAIN ; 'Teresa Rodriguez' ; Departamento de Quimica Facultad de Ciencias Universidad de Burgos 09001 BURGOS SPAIN ; 'Tomas Torroba' ; Departamento de Quimica Facultad de Ciencias Universidad de Burgos 09001 BURGOS SPAIN ; _publ_section_title ; Cyclopentathiadiazines, new heterocyclic materials from cyclic enaminonitriles ; #-------------------------- data section of block --------------------------- data_Compound_5_(sm1032am) _database_code_depnum_ccdc_archive 'CCDC 247923' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H12 Cl N3 O S' _chemical_formula_weight 305.78 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c 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' '-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 16.356(6) _cell_length_b 11.871(4) _cell_length_c 15.296(5) _cell_angle_alpha 90.00 _cell_angle_beta 114.333(7) _cell_angle_gamma 90.00 _cell_volume 2706.0(17) _cell_formula_units_Z 8 _cell_measurement_temperature 299(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description PRISM _exptl_crystal_colour ORANGE_RED _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.27 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.501 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1264 _exptl_absorpt_coefficient_mu 0.435 _exptl_absorpt_correction_type SADABS _exptl_absorpt_correction_T_min 0.411093 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 299(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5954 _diffrn_reflns_av_R_equivalents 0.0582 _diffrn_reflns_av_sigmaI/netI 0.0490 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.19 _diffrn_reflns_theta_max 23.33 _reflns_number_total 1957 _reflns_number_gt 1363 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0741P)^2^+1.2002P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1957 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0834 _refine_ls_R_factor_gt 0.0509 _refine_ls_wR_factor_ref 0.1368 _refine_ls_wR_factor_gt 0.1196 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _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 Cl1 Cl 0.09208(8) 0.42774(8) 0.19215(7) 0.0499(4) Uani 1 1 d . . . S1 S 0.13777(8) 0.26858(9) 0.56194(7) 0.0463(4) Uani 1 1 d . . . N1 N 0.1412(2) 0.1739(2) 0.4857(2) 0.0401(8) Uani 1 1 d . . . N2 N 0.1365(2) 0.3959(2) 0.5206(2) 0.0395(8) Uani 1 1 d . . . N3 N 0.1350(2) 0.5275(2) 0.4079(2) 0.0350(8) Uani 1 1 d . . . O1 O 0.1603(2) 0.7586(2) 0.3828(2) 0.0590(9) Uani 1 1 d . . . C1 C 0.1367(2) 0.2076(3) 0.4032(3) 0.0321(9) Uani 1 1 d . . . C2 C 0.1265(3) 0.1352(3) 0.3229(3) 0.0360(9) Uani 1 1 d . . . C3 C 0.1279(3) 0.0182(3) 0.3145(3) 0.0491(11) Uani 1 1 d . . . H3 H 0.1404 -0.0285 0.3673 0.059 Uiso 1 1 calc R . . C4 C 0.1100(3) -0.0253(4) 0.2249(3) 0.0569(13) Uani 1 1 d . . . H4 H 0.1111 -0.1029 0.2177 0.068 Uiso 1 1 calc R . . C5 C 0.0904(3) 0.0425(4) 0.1460(3) 0.0549(12) Uani 1 1 d . . . H5 H 0.0776 0.0098 0.0865 0.066 Uiso 1 1 calc R . . C6 C 0.0894(3) 0.1585(4) 0.1534(3) 0.0435(10) Uani 1 1 d . . . H6 H 0.0760 0.2042 0.0999 0.052 Uiso 1 1 calc R . . C7 C 0.1090(2) 0.2047(3) 0.2431(3) 0.0327(9) Uani 1 1 d . . . C8 C 0.1119(2) 0.3211(3) 0.2737(3) 0.0324(9) Uani 1 1 d . . . C9 C 0.1307(2) 0.3261(3) 0.3699(2) 0.0297(9) Uani 1 1 d . . . C10 C 0.1360(2) 0.4163(3) 0.4355(3) 0.0327(9) Uani 1 1 d . . . C11 C 0.2087(3) 0.5656(3) 0.3849(3) 0.0414(10) Uani 1 1 d . . . H11A H 0.2215 0.5093 0.3463 0.050 Uiso 1 1 calc R . . H11B H 0.2623 0.5764 0.4435 0.050 Uiso 1 1 calc R . . C12 C 0.1826(3) 0.6746(3) 0.3306(3) 0.0505(11) Uani 1 1 d . . . H12A H 0.2319 0.7010 0.3165 0.061 Uiso 1 1 calc R . . H12B H 0.1315 0.6617 0.2701 0.061 Uiso 1 1 calc R . . C13 C 0.0898(3) 0.7202(3) 0.4063(3) 0.0554(13) Uani 1 1 d . . . H13A H 0.0367 0.7076 0.3475 0.066 Uiso 1 1 calc R . . H13B H 0.0757 0.7782 0.4425 0.066 Uiso 1 1 calc R . . C14 C 0.1129(3) 0.6131(3) 0.4640(3) 0.0479(12) Uani 1 1 d . . . H14A H 0.1638 0.6254 0.5248 0.057 Uiso 1 1 calc R . . H14B H 0.0624 0.5884 0.4769 0.057 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 Cl1 0.0584(8) 0.0527(6) 0.0347(6) 0.0114(5) 0.0152(5) 0.0034(5) S1 0.0508(8) 0.0531(6) 0.0352(6) 0.0086(5) 0.0181(5) 0.0001(5) N1 0.031(2) 0.0459(18) 0.038(2) 0.0103(15) 0.0090(16) -0.0006(16) N2 0.038(2) 0.0497(19) 0.0315(19) 0.0027(15) 0.0151(17) 0.0008(16) N3 0.034(2) 0.0361(17) 0.0388(19) 0.0008(15) 0.0188(16) -0.0006(15) O1 0.066(2) 0.0429(16) 0.064(2) 0.0045(15) 0.0234(19) -0.0046(16) C1 0.018(2) 0.039(2) 0.034(2) 0.0059(17) 0.0057(17) 0.0013(17) C2 0.020(2) 0.041(2) 0.042(2) -0.0006(18) 0.0080(19) 0.0022(17) C3 0.044(3) 0.044(2) 0.052(3) -0.001(2) 0.013(2) 0.003(2) C4 0.053(3) 0.047(2) 0.067(3) -0.010(2) 0.022(3) 0.003(2) C5 0.043(3) 0.066(3) 0.053(3) -0.020(2) 0.017(2) -0.002(2) C6 0.033(3) 0.060(3) 0.037(2) -0.005(2) 0.014(2) -0.002(2) C7 0.019(2) 0.043(2) 0.037(2) 0.0007(18) 0.0120(18) 0.0033(17) C8 0.020(2) 0.042(2) 0.034(2) 0.0041(17) 0.0109(18) 0.0029(17) C9 0.019(2) 0.040(2) 0.030(2) 0.0047(17) 0.0103(17) -0.0011(17) C10 0.019(2) 0.044(2) 0.033(2) 0.0016(17) 0.0088(18) 0.0014(18) C11 0.031(3) 0.048(2) 0.043(2) 0.0064(19) 0.013(2) -0.001(2) C12 0.038(3) 0.054(3) 0.058(3) 0.016(2) 0.019(2) 0.000(2) C13 0.068(4) 0.047(2) 0.052(3) -0.003(2) 0.026(3) 0.008(2) C14 0.057(3) 0.044(2) 0.045(3) -0.0048(19) 0.023(2) -0.004(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 Cl1 C8 1.712(4) . ? S1 N2 1.636(3) . ? S1 N1 1.638(3) . ? N1 C1 1.296(4) . ? N2 C10 1.320(5) . ? N3 C10 1.384(4) . ? N3 C11 1.459(5) . ? N3 C14 1.468(4) . ? O1 C12 1.417(5) . ? O1 C13 1.417(5) . ? C1 C2 1.452(5) . ? C1 C9 1.486(5) . ? C2 C3 1.395(5) . ? C2 C7 1.402(5) . ? C3 C4 1.378(6) . ? C4 C5 1.375(6) . ? C5 C6 1.382(6) . ? C6 C7 1.386(5) . ? C7 C8 1.453(5) . ? C8 C9 1.375(5) . ? C9 C10 1.446(5) . ? C11 C12 1.502(5) . ? C13 C14 1.505(5) . ? 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 N2 S1 N1 110.93(16) . . ? C1 N1 S1 118.5(2) . . ? C10 N2 S1 123.0(3) . . ? C10 N3 C11 117.6(3) . . ? C10 N3 C14 117.1(3) . . ? C11 N3 C14 110.7(3) . . ? C12 O1 C13 110.0(3) . . ? N1 C1 C2 125.6(3) . . ? N1 C1 C9 126.5(3) . . ? C2 C1 C9 107.6(3) . . ? C3 C2 C7 120.7(3) . . ? C3 C2 C1 131.8(4) . . ? C7 C2 C1 107.4(3) . . ? C4 C3 C2 117.3(4) . . ? C5 C4 C3 122.1(4) . . ? C4 C5 C6 121.1(4) . . ? C5 C6 C7 118.0(4) . . ? C6 C7 C2 120.6(3) . . ? C6 C7 C8 131.2(3) . . ? C2 C7 C8 108.1(3) . . ? C9 C8 C7 110.5(3) . . ? C9 C8 Cl1 129.7(3) . . ? C7 C8 Cl1 119.8(3) . . ? C8 C9 C10 134.3(3) . . ? C8 C9 C1 106.3(3) . . ? C10 C9 C1 119.1(3) . . ? N2 C10 N3 118.1(3) . . ? N2 C10 C9 121.5(3) . . ? N3 C10 C9 120.3(3) . . ? N3 C11 C12 109.0(3) . . ? O1 C12 C11 112.0(3) . . ? O1 C13 C14 112.7(4) . . ? N3 C14 C13 107.7(3) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 23.33 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.331 _refine_diff_density_min -0.335 _refine_diff_density_rms 0.066 #===END data_Compound_6_(sm761am) _database_code_depnum_ccdc_archive 'CCDC 247924' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H8 Cl3 N3 O S' _chemical_formula_weight 324.60 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' Cl Cl 0.1484 0.1585 '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 7.2261(10) _cell_length_b 8.9133(12) _cell_length_c 10.0492(13) _cell_angle_alpha 98.589(3) _cell_angle_beta 93.045(3) _cell_angle_gamma 99.426(2) _cell_volume 629.35(15) _cell_formula_units_Z 2 _cell_measurement_temperature 299(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description PRISM _exptl_crystal_colour RED _exptl_crystal_size_max 0.09 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.29 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.713 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 328 _exptl_absorpt_coefficient_mu 0.883 _exptl_absorpt_correction_type SADABS _exptl_absorpt_correction_T_min 0.386569 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 299(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2820 _diffrn_reflns_av_R_equivalents 0.0145 _diffrn_reflns_av_sigmaI/netI 0.0165 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 23.26 _reflns_number_total 1768 _reflns_number_gt 1598 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0603P)^2^+0.2612P] 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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.011(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1768 _refine_ls_number_parameters 164 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0364 _refine_ls_R_factor_gt 0.0335 _refine_ls_wR_factor_ref 0.0988 _refine_ls_wR_factor_gt 0.0965 _refine_ls_goodness_of_fit_ref 1.094 _refine_ls_restrained_S_all 1.094 _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 Cl1 Cl 0.49335(11) 0.54971(9) 0.65606(7) 0.0547(3) Uani 1 1 d . . . Cl2 Cl 0.82654(11) 0.51535(9) 0.87723(8) 0.0587(3) Uani 1 1 d . . . Cl3 Cl 0.78377(11) 0.72749(9) 1.18066(7) 0.0560(3) Uani 1 1 d . . . S1 S 0.21570(10) 0.92032(8) 1.08493(6) 0.0472(3) Uani 1 1 d . . . O1 O 0.0733(3) 0.8198(3) 0.43276(19) 0.0634(6) Uani 1 1 d . . . N1 N 0.4105(3) 0.8649(3) 1.1194(2) 0.0432(6) Uani 1 1 d . . . N2 N 0.1548(3) 0.8861(3) 0.9249(2) 0.0418(5) Uani 1 1 d . . . N3 N 0.1919(3) 0.7973(2) 0.7012(2) 0.0396(5) Uani 1 1 d . . . C1 C 0.2534(3) 0.8138(3) 0.8361(2) 0.0361(6) Uani 1 1 d . . . C2 C 0.4113(3) 0.7497(3) 0.8778(2) 0.0360(6) Uani 1 1 d . . . C3 C 0.4867(3) 0.7882(3) 1.0209(2) 0.0357(6) Uani 1 1 d . . . C4 C 0.6462(4) 0.7155(3) 1.0351(3) 0.0414(6) Uani 1 1 d . . . C5 C 0.6638(4) 0.6306(3) 0.9130(3) 0.0403(6) Uani 1 1 d . . . C6 C 0.5198(4) 0.6504(3) 0.8165(2) 0.0393(6) Uani 1 1 d . . . C7 C 0.3257(4) 0.8551(3) 0.6077(3) 0.0462(7) Uani 1 1 d . . . H7A H 0.4478 0.8283 0.6280 0.055 Uiso 1 1 calc R . . H7B H 0.3403 0.9664 0.6175 0.055 Uiso 1 1 calc R . . C8 C 0.2521(5) 0.7837(4) 0.4648(3) 0.0565(8) Uani 1 1 d . . . H8A H 0.3396 0.8213 0.4024 0.068 Uiso 1 1 calc R . . H8B H 0.2428 0.6727 0.4547 0.068 Uiso 1 1 calc R . . C9 C -0.0565(5) 0.7654(4) 0.5236(3) 0.0597(8) Uani 1 1 d . . . H9A H -0.0702 0.6541 0.5140 0.072 Uiso 1 1 calc R . . H9B H -0.1786 0.7905 0.5003 0.072 Uiso 1 1 calc R . . C10 C 0.0062(4) 0.8349(3) 0.6684(3) 0.0469(7) Uani 1 1 d . . . H10A H 0.0134 0.9458 0.6805 0.056 Uiso 1 1 calc R . . H10B H -0.0835 0.7935 0.7279 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 Cl1 0.0697(5) 0.0620(5) 0.0316(4) -0.0075(3) -0.0005(3) 0.0246(4) Cl2 0.0589(5) 0.0572(5) 0.0645(5) 0.0096(4) -0.0011(4) 0.0251(4) Cl3 0.0593(5) 0.0676(5) 0.0390(4) 0.0119(3) -0.0146(3) 0.0079(4) S1 0.0498(5) 0.0587(5) 0.0313(4) -0.0022(3) 0.0071(3) 0.0114(3) O1 0.0761(15) 0.0840(15) 0.0357(11) 0.0108(10) -0.0064(10) 0.0326(12) N1 0.0494(13) 0.0494(13) 0.0272(11) 0.0021(9) 0.0019(9) 0.0018(10) N2 0.0417(12) 0.0501(13) 0.0326(12) 0.0011(10) 0.0033(9) 0.0102(10) N3 0.0420(12) 0.0491(13) 0.0286(11) 0.0059(9) -0.0006(9) 0.0117(10) C1 0.0392(14) 0.0362(13) 0.0308(13) 0.0029(10) 0.0023(11) 0.0024(11) C2 0.0390(13) 0.0400(14) 0.0266(13) 0.0029(10) -0.0001(10) 0.0030(11) C3 0.0390(14) 0.0380(14) 0.0283(13) 0.0048(11) 0.0025(10) 0.0017(11) C4 0.0450(15) 0.0452(14) 0.0317(14) 0.0090(11) -0.0060(11) 0.0017(12) C5 0.0399(14) 0.0419(14) 0.0403(15) 0.0088(12) 0.0021(11) 0.0088(11) C6 0.0475(15) 0.0407(14) 0.0276(13) 0.0002(11) 0.0013(11) 0.0069(12) C7 0.0515(16) 0.0537(17) 0.0352(15) 0.0095(12) 0.0041(12) 0.0117(13) C8 0.070(2) 0.073(2) 0.0318(15) 0.0082(13) 0.0047(13) 0.0254(16) C9 0.0579(18) 0.075(2) 0.0457(17) 0.0040(15) -0.0154(14) 0.0206(16) C10 0.0478(16) 0.0561(17) 0.0374(15) 0.0049(12) -0.0025(12) 0.0152(13) _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 Cl1 C6 1.709(2) . ? Cl2 C5 1.702(3) . ? Cl3 C4 1.704(3) . ? S1 N1 1.604(3) . ? S1 N2 1.614(2) . ? O1 C8 1.414(4) . ? O1 C9 1.422(4) . ? N1 C3 1.314(3) . ? N2 C1 1.329(3) . ? N3 C1 1.383(3) . ? N3 C10 1.467(3) . ? N3 C7 1.471(3) . ? C1 C2 1.427(4) . ? C2 C6 1.376(4) . ? C2 C3 1.480(3) . ? C3 C4 1.423(4) . ? C4 C5 1.366(4) . ? C5 C6 1.435(4) . ? C7 C8 1.512(4) . ? C9 C10 1.509(4) . ? 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 N1 S1 N2 111.88(11) . . ? C8 O1 C9 110.0(2) . . ? C3 N1 S1 118.25(19) . . ? C1 N2 S1 122.47(19) . . ? C1 N3 C10 117.7(2) . . ? C1 N3 C7 118.2(2) . . ? C10 N3 C7 109.9(2) . . ? N2 C1 N3 117.1(2) . . ? N2 C1 C2 121.7(2) . . ? N3 C1 C2 121.1(2) . . ? C6 C2 C1 135.6(2) . . ? C6 C2 C3 105.6(2) . . ? C1 C2 C3 118.8(2) . . ? N1 C3 C4 126.0(2) . . ? N1 C3 C2 126.0(2) . . ? C4 C3 C2 107.8(2) . . ? C5 C4 C3 107.7(2) . . ? C5 C4 Cl3 126.6(2) . . ? C3 C4 Cl3 125.6(2) . . ? C4 C5 C6 109.4(2) . . ? C4 C5 Cl2 126.6(2) . . ? C6 C5 Cl2 124.0(2) . . ? C2 C6 C5 109.4(2) . . ? C2 C6 Cl1 129.3(2) . . ? C5 C6 Cl1 121.2(2) . . ? N3 C7 C8 108.9(2) . . ? O1 C8 C7 111.1(2) . . ? O1 C9 C10 112.1(3) . . ? N3 C10 C9 108.4(2) . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 23.26 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.248 _refine_diff_density_min -0.321 _refine_diff_density_rms 0.053 #===END #-------------------------- data section of block --------------------------- data_Compound_4_(sm106am) _database_code_depnum_ccdc_archive 'CCDC 250853' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H4 Cl2 N2 S' _chemical_formula_weight 255.11 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' Cl Cl 0.1484 0.1585 '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 6.888(4) _cell_length_b 8.696(5) _cell_length_c 9.612(5) _cell_angle_alpha 68.241(9) _cell_angle_beta 83.001(10) _cell_angle_gamma 70.332(10) _cell_volume 503.5(5) _cell_formula_units_Z 2 _cell_measurement_temperature 299(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description NEEDLE _exptl_crystal_colour RED _exptl_crystal_size_max 0.03 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.45 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.683 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 256 _exptl_absorpt_coefficient_mu 0.812 _exptl_absorpt_correction_type SADABS _exptl_absorpt_correction_T_min 0.620117 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 299(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2285 _diffrn_reflns_av_R_equivalents 0.0217 _diffrn_reflns_av_sigmaI/netI 0.0389 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.28 _diffrn_reflns_theta_max 23.31 _reflns_number_total 1452 _reflns_number_gt 1090 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0896P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1452 _refine_ls_number_parameters 136 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0670 _refine_ls_R_factor_gt 0.0489 _refine_ls_wR_factor_ref 0.1375 _refine_ls_wR_factor_gt 0.1289 _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_restrained_S_all 1.017 _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 Cl1 Cl 0.3856(2) 0.29247(15) 0.78858(15) 0.0659(5) Uani 1 1 d . . . Cl2 Cl 0.28425(19) 0.68603(16) 0.52611(12) 0.0590(4) Uani 1 1 d . . . S1 S 0.0851(2) 0.99080(13) 0.79372(13) 0.0538(4) Uani 1 1 d . . . N1 N 0.1169(5) 0.8322(4) 0.9572(4) 0.0421(9) Uani 1 1 d . . . N2 N 0.1551(6) 0.9122(5) 0.6579(4) 0.0480(9) Uani 1 1 d . . . C1 C 0.3032(6) 0.4351(5) 0.8850(4) 0.0370(10) Uani 1 1 d . . . C2 C 0.2409(6) 0.6111(5) 0.8303(4) 0.0317(9) Uani 1 1 d . . . C3 C 0.1863(6) 0.6688(5) 0.9621(4) 0.0320(9) Uani 1 1 d . . . C4 C 0.2209(6) 0.5152(5) 1.0949(4) 0.0341(9) Uani 1 1 d . . . C5 C 0.1932(7) 0.4918(6) 1.2470(5) 0.0504(11) Uani 1 1 d . . . H5 H 0.1443 0.5868 1.2788 0.061 Uiso 1 1 calc R . . C6 C 0.2409(8) 0.3224(7) 1.3488(5) 0.0616(14) Uani 1 1 d . . . H6 H 0.2259 0.3040 1.4506 0.074 Uiso 1 1 calc R . . C7 C 0.3099(7) 0.1809(7) 1.3029(5) 0.0624(14) Uani 1 1 d . . . H7 H 0.3379 0.0692 1.3746 0.075 Uiso 1 1 calc R . . C8 C 0.3387(7) 0.1997(6) 1.1538(5) 0.0535(12) Uani 1 1 d . . . H8 H 0.3874 0.1028 1.1245 0.064 Uiso 1 1 calc R . . C9 C 0.2923(6) 0.3694(5) 1.0476(5) 0.0376(10) Uani 1 1 d . . . C10 C 0.2191(6) 0.7457(5) 0.6833(4) 0.0369(10) Uani 1 1 d . . . 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 0.0849(10) 0.0455(7) 0.0717(8) -0.0356(6) 0.0066(7) -0.0112(6) Cl2 0.0696(9) 0.0684(8) 0.0358(6) -0.0226(6) 0.0048(5) -0.0145(6) S1 0.0733(9) 0.0314(6) 0.0522(7) -0.0125(5) -0.0047(6) -0.0116(6) N1 0.045(2) 0.036(2) 0.046(2) -0.0174(16) -0.0042(16) -0.0080(16) N2 0.052(2) 0.040(2) 0.040(2) -0.0025(15) -0.0015(17) -0.0132(18) C1 0.034(2) 0.037(2) 0.044(2) -0.0208(19) 0.0020(18) -0.0093(19) C2 0.032(2) 0.035(2) 0.030(2) -0.0121(17) 0.0015(17) -0.0109(18) C3 0.028(2) 0.036(2) 0.036(2) -0.0170(18) 0.0004(17) -0.0114(18) C4 0.029(2) 0.042(2) 0.030(2) -0.0104(18) -0.0025(16) -0.0118(19) C5 0.050(3) 0.063(3) 0.037(3) -0.014(2) -0.007(2) -0.019(2) C6 0.057(3) 0.081(4) 0.038(3) -0.004(3) -0.010(2) -0.025(3) C7 0.052(3) 0.059(3) 0.052(3) 0.017(3) -0.013(2) -0.024(3) C8 0.041(3) 0.044(3) 0.064(3) -0.005(2) -0.008(2) -0.012(2) C9 0.026(2) 0.031(2) 0.050(3) -0.0088(19) -0.0058(18) -0.0070(18) C10 0.034(2) 0.042(3) 0.036(2) -0.0145(19) 0.0014(18) -0.0131(19) _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 Cl1 C1 1.723(4) . ? Cl2 C10 1.736(4) . ? S1 N2 1.640(4) . ? S1 N1 1.641(4) . ? N1 C3 1.322(5) . ? N2 C10 1.298(5) . ? C1 C2 1.349(5) . ? C1 C9 1.454(6) . ? C2 C10 1.448(5) . ? C2 C3 1.492(5) . ? C3 C4 1.437(5) . ? C4 C5 1.398(5) . ? C4 C9 1.418(5) . ? C5 C6 1.385(7) . ? C6 C7 1.376(7) . ? C7 C8 1.378(7) . ? C8 C9 1.402(6) . ? 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 N2 S1 N1 110.67(17) . . ? C3 N1 S1 119.1(3) . . ? C10 N2 S1 122.1(3) . . ? C2 C1 C9 110.9(3) . . ? C2 C1 Cl1 128.8(3) . . ? C9 C1 Cl1 120.3(3) . . ? C1 C2 C10 136.1(3) . . ? C1 C2 C3 106.6(3) . . ? C10 C2 C3 117.3(3) . . ? N1 C3 C4 126.3(3) . . ? N1 C3 C2 126.0(3) . . ? C4 C3 C2 107.8(3) . . ? C5 C4 C9 120.5(4) . . ? C5 C4 C3 132.4(4) . . ? C9 C4 C3 107.0(3) . . ? C6 C5 C4 117.8(4) . . ? C7 C6 C5 121.6(4) . . ? C6 C7 C8 121.9(4) . . ? C7 C8 C9 118.0(4) . . ? C8 C9 C4 120.1(4) . . ? C8 C9 C1 132.3(4) . . ? C4 C9 C1 107.7(3) . . ? N2 C10 C2 124.9(4) . . ? N2 C10 Cl2 115.8(3) . . ? C2 C10 Cl2 119.3(3) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 23.31 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.529 _refine_diff_density_min -0.286 _refine_diff_density_rms 0.072 #===END