Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2001 data_global # SUBMISSION DETAILS _publ_contact_author_name 'Dr. I. Yu. Bagryanskaya' _publ_contact_author_email bagryan@nioch.nsc.ru _publ_contact_letter ; Please deposit these two compounds and send us deposition numbers. ; _publ_requested_journal 'Chemical Communication' loop_ _publ_author_name 'Makarov, A. S.' 'Shakirov, M. M.' 'Shuvaev, T. V.' 'Bagryanskaya, I. Yu.' 'Gatilov, Yu. V.' 'Zibarev, A. V.' #============================================================================== data_compound2_M195 _database_code_CSD 164031 _audit_creation_method SHELXL-97 _chemical_name_systematic ; Dibenzo[d,i]-3H,8H-1,2,6,7,3,8-tetrathiadidiazecine ; _chemical_name_common ? _chemical_formula_moiety 'C12 H10 N2 S4' _chemical_formula_sum 'C12 H10 N2 S4' _chemical_formula_weight 310.46 _chemical_melting_point 488-490 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 'P 21/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 8.1005(16) _cell_length_b 4.7156(9) _cell_length_c 16.905(5) _cell_angle_alpha 90.00 _cell_angle_beta 95.565(17) _cell_angle_gamma 90.00 _cell_volume 642.7(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 18 _cell_measurement_theta_min 9.73 _cell_measurement_theta_max 11.58 _exptl_crystal_description 'plate' _exptl_crystal_colour 'light yellow' _exptl_crystal_size_max 0.04 _exptl_crystal_size_mid 0.86 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.604 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 320 _exptl_absorpt_coefficient_mu 0.719 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_crystal_preparation toluene _exptl_special_details ; 'Crystallization solvent toluene' ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '2\q/\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 1.89 _diffrn_reflns_number 875 _diffrn_reflns_av_R_equivalents 0.0374 _diffrn_reflns_av_sigmaI/netI 0.1151 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.42 _diffrn_reflns_theta_max 22.49 _reflns_number_total 807 _reflns_number_gt 505 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker XSCANS' _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 w=1/[\s^2^(Fo^2^)+(0.1507P)^2^+1.9214P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.000(11) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 807 _refine_ls_number_parameters 103 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1190 _refine_ls_R_factor_gt 0.0873 _refine_ls_wR_factor_ref 0.2859 _refine_ls_wR_factor_gt 0.2766 _refine_ls_goodness_of_fit_ref 1.157 _refine_ls_restrained_S_all 1.157 _refine_ls_shift/su_max 0.236 _refine_ls_shift/su_mean 0.004 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.0078(5) 0.1968(7) 0.6159(2) 0.0405(13) Uani 1 d . . . S2 S 0.1949(4) 0.5297(8) 0.39098(19) 0.0394(13) Uani 1 d . . . C3 C 0.1763(14) 0.446(2) 0.6192(7) 0.024(3) Uani 1 d . . . N4 N 0.2049(16) 0.374(3) 0.4792(7) 0.042(4) Uani 1 d . . . C5 C 0.2314(18) 0.569(3) 0.6923(8) 0.044(4) Uani 1 d . . . C6 C 0.3766(16) 0.720(3) 0.5570(8) 0.037(3) Uani 1 d . . . C7 C 0.3528(19) 0.769(3) 0.6968(9) 0.048(4) Uani 1 d . . . C8 C 0.2487(15) 0.516(3) 0.5522(7) 0.032(3) Uani 1 d . . . C1 C 0.4229(18) 0.846(3) 0.6281(8) 0.043(4) Uani 1 d . . . H1A H 0.513(14) 0.99(2) 0.638(6) 0.02(3) Uiso 1 d . . . H6 H 0.408(15) 0.77(3) 0.495(8) 0.06(4) Uiso 1 d . . . H6' H 0.386(15) 0.87(3) 0.748(8) 0.05(4) Uiso 1 d . . . H5 H 0.175(16) 0.53(3) 0.738(7) 0.04(4) Uiso 1 d . . . H4N H 0.150(15) 0.27(2) 0.486(7) 0.01(4) Uiso 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 S1 0.041(2) 0.033(2) 0.048(2) 0.0016(17) 0.0077(15) -0.0048(18) S2 0.033(2) 0.047(2) 0.040(2) -0.0029(17) 0.0107(14) -0.0024(18) C3 0.017(7) 0.014(6) 0.039(7) -0.002(6) -0.003(5) 0.003(5) N4 0.033(8) 0.040(8) 0.055(8) -0.004(7) 0.017(6) -0.009(7) C5 0.045(10) 0.046(9) 0.043(9) -0.002(8) 0.007(7) -0.001(8) C6 0.025(8) 0.033(8) 0.054(9) 0.006(7) 0.003(6) -0.002(7) C7 0.048(10) 0.042(9) 0.054(10) -0.012(8) 0.003(8) -0.001(8) C8 0.034(8) 0.026(7) 0.035(7) -0.003(6) 0.000(6) 0.007(7) C1 0.037(9) 0.037(8) 0.051(9) -0.008(7) -0.016(7) -0.001(8) _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 C3 1.797(12) . ? S1 S2 2.082(5) 3_566 ? S2 N4 1.657(14) . ? S2 S1 2.082(5) 3_566 ? C3 C8 1.366(16) . ? C3 C5 1.399(17) . ? N4 C8 1.416(17) . ? C5 C7 1.36(2) . ? C6 C1 1.363(18) . ? C6 C8 1.410(17) . ? C7 C1 1.39(2) . ? 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 C3 S1 S2 100.9(4) . 3_566 ? N4 S2 S1 107.1(5) . 3_566 ? C8 C3 C5 120.4(11) . . ? C8 C3 S1 121.2(9) . . ? C5 C3 S1 118.4(10) . . ? C8 N4 S2 124.2(11) . . ? C7 C5 C3 120.3(14) . . ? C1 C6 C8 119.2(13) . . ? C5 C7 C1 119.2(14) . . ? C3 C8 C6 119.3(11) . . ? C3 C8 N4 121.1(12) . . ? C6 C8 N4 119.5(12) . . ? C6 C1 C7 121.5(15) . . ? 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 N4 S2 S1 C3 68.3(7) 3_566 3_566 . . ? S2 S1 C3 C8 -97.2(10) 3_566 . . . ? S1 C3 C8 N4 -6.4(16) . . . . ? C3 C8 N4 S2 144.4(11) . . . . ? C8 N4 S2 S1 -69.4(12) . . . 3_566 ? N4 S2 S1 C3 -68.3(7) . . 3_566 3_566 ? _diffrn_measured_fraction_theta_max 0.843 _diffrn_reflns_theta_full 22.49 _diffrn_measured_fraction_theta_full 0.843 _refine_diff_density_max 0.829 _refine_diff_density_min -0.499 _refine_diff_density_rms 0.147 #============================================================================== data_compound11_SH28I _database_code_CSD 164032 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 7-iodo-1,2,4,3,5-Benzotrithiadiazepine ; _chemical_name_common ? _chemical_formula_moiety 'C6 H3 I1 N2 S3' _chemical_formula_sum 'C6 H3 I1 N2 S3' _chemical_formula_weight 326.18 _chemical_melting_point 373-374 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' 'I' 'I' -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/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 4.1174(19) _cell_length_b 11.048(7) _cell_length_c 20.633(10) _cell_angle_alpha 90.00 _cell_angle_beta 91.74(5) _cell_angle_gamma 90.00 _cell_volume 938.2(9) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 40 _cell_measurement_theta_min 9.6 _cell_measurement_theta_max 11.3 _exptl_crystal_description needle _exptl_crystal_colour red-brown _exptl_crystal_size_max 0.80 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.309 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 616 _exptl_absorpt_coefficient_mu 4.023 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.6031 _exptl_absorpt_correction_T_max 0.8201 _exptl_absorpt_process_details ? _exptl_crystal_preparation hexane _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 1.1 _diffrn_reflns_number 1859 _diffrn_reflns_av_R_equivalents 0.0396 _diffrn_reflns_av_sigmaI/netI 0.0804 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.70 _diffrn_reflns_theta_max 25.01 _reflns_number_total 1616 _reflns_number_gt 943 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _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^)+(0.1500P)^2^+3.1282P] 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 1616 _refine_ls_number_parameters 109 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1369 _refine_ls_R_factor_gt 0.0831 _refine_ls_wR_factor_ref 0.2639 _refine_ls_wR_factor_gt 0.2220 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _refine_ls_shift/su_max 0.016 _refine_ls_shift/su_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_adp_type _atom_site_occupancy _atom_site_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I1 I -0.9831(3) 0.31306(12) -0.34341(4) 0.0706(4) Uani 1 1 d . . . S1 S -0.2321(10) 0.4057(4) -0.06014(17) 0.0632(11) Uani 1 1 d . . . S2 S -0.4398(12) 0.3084(4) 0.01241(18) 0.0715(12) Uani 1 1 d . . . N3 N -0.291(5) 0.1667(14) 0.0034(7) 0.098(6) Uani 1 1 d . . . S4 S -0.2821(15) 0.0994(4) -0.0606(2) 0.0867(16) Uani 1 1 d . . . N5 N -0.364(4) 0.1507(12) -0.1290(6) 0.070(4) Uani 1 1 d . . . C6 C -0.651(3) 0.2418(14) -0.2164(6) 0.049(3) Uani 1 1 d . . . H6 H -0.6696 0.1650 -0.2345 0.059 Uiso 1 1 calc R . . C7 C -0.772(4) 0.3408(14) -0.2503(6) 0.056(4) Uani 1 1 d . . . C8 C -0.743(4) 0.4527(14) -0.2260(7) 0.064(4) Uani 1 1 d . . . H8 H -0.8250 0.5186 -0.2494 0.077 Uiso 1 1 calc R . . C9 C -0.592(4) 0.4700(14) -0.1663(6) 0.059(4) Uani 1 1 d . . . H9 H -0.5696 0.5479 -0.1497 0.071 Uiso 1 1 calc R . . C9A C -0.470(3) 0.3710(13) -0.1303(6) 0.045(3) Uani 1 1 d . . . C5A C -0.505(3) 0.2557(15) -0.1561(5) 0.050(4) 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 I1 0.0675(7) 0.0988(9) 0.0444(5) -0.0020(5) -0.0182(5) -0.0100(6) S1 0.072(3) 0.070(3) 0.0460(18) 0.0005(17) -0.0162(18) -0.006(2) S2 0.091(3) 0.084(3) 0.0385(18) 0.0039(19) -0.0160(19) 0.006(2) N3 0.153(15) 0.075(10) 0.064(9) 0.020(7) -0.044(10) 0.018(10) S4 0.129(4) 0.067(3) 0.062(2) 0.015(2) -0.023(3) 0.018(3) N5 0.099(10) 0.062(8) 0.048(6) 0.003(6) -0.018(7) 0.006(8) C6 0.052(8) 0.054(8) 0.042(7) -0.002(6) 0.000(6) -0.003(7) C7 0.066(10) 0.066(10) 0.035(7) 0.000(6) 0.003(7) -0.004(8) C8 0.081(11) 0.049(8) 0.061(8) 0.011(7) -0.020(8) 0.008(8) C9 0.080(10) 0.047(8) 0.050(8) -0.006(6) -0.008(7) 0.011(8) C9A 0.043(7) 0.053(8) 0.039(6) -0.001(6) 0.004(5) -0.012(7) C5A 0.059(9) 0.066(9) 0.026(6) 0.009(6) 0.003(6) -0.011(8) _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 I1 C7 2.106(14) . ? S1 C9A 1.764(13) . ? S1 S2 2.051(6) . ? S2 N3 1.692(16) . ? N3 S4 1.517(16) . ? S4 N5 1.550(13) . ? N5 C5A 1.41(2) . ? C6 C5A 1.374(17) . ? C6 C7 1.38(2) . ? C7 C8 1.34(2) . ? C8 C9 1.377(19) . ? C9 C9A 1.41(2) . ? C9A C5A 1.39(2) . ? 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 C9A S1 S2 104.6(5) . . ? N3 S2 S1 104.2(6) . . ? S4 N3 S2 124.6(9) . . ? N3 S4 N5 127.1(8) . . ? C5A N5 S4 137.7(11) . . ? C5A C6 C7 120.8(14) . . ? C8 C7 C6 121.0(13) . . ? C8 C7 I1 120.3(11) . . ? C6 C7 I1 118.6(11) . . ? C7 C8 C9 119.7(14) . . ? C8 C9 C9A 120.6(14) . . ? C5A C9A C9 118.7(12) . . ? C5A C9A S1 124.4(11) . . ? C9 C9A S1 116.4(11) . . ? C6 C5A C9A 119.2(14) . . ? C6 C5A N5 115.6(14) . . ? C9A C5A N5 124.6(12) . . ? 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 C9A S1 S2 N3 80.2(8) . . . . ? S1 S2 N3 S4 -47.5(15) . . . . ? S2 N3 S4 N5 8(2) . . . . ? N3 S4 N5 C5A -11(2) . . . . ? S4 N5 C5A C9A 35(3) . . . . ? N5 C5A C9A S1 2(2) . . . . ? C5A C9A S1 S2 -61.2(12) . . . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 2.160 _refine_diff_density_min -0.801 _refine_diff_density_rms 0.244