# Supplementary Material (ESI) for New Journal of Chemistry # This journal is (c) The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2008 data_global _journal_name_full 'New J.Chem.' _journal_coden_Cambridge 0440 _publ_contact_author_name 'Oksana Makota' _publ_contact_author_address ; Institute of Chemistry and Chemical Technologies Lviv National Polytechnic University Lviv 79013 UKRAINE ; _publ_contact_author_email 'O MAKOTA@POLYNET.LVIV.UA' _publ_section_title ; Novel hydroperoxy sultam, 2-(6-bromo-pyrid-2-yl)-2, 3,4,5,6,7-hexahydro-1,2-benzisothiazol-3-hydroperoxy 1,1-dioxide: synthesis, crystal structure and kinetics of catalytic interaction with cyclooctene ; loop_ _publ_author_name 'Oksana Makota' 'A. Eilfeld' 'Barbel Schulze' 'Joachim Sieler' 'Yu. Trach' data_ip2-74_am56 _database_code_depnum_ccdc_archive 'CCDC 662843' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H13 Br N2 O4 S' _chemical_formula_weight 361.21 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' Br Br -0.2901 2.4595 '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)/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 8.8338(7) _cell_length_b 11.9410(6) _cell_length_c 12.9247(8) _cell_angle_alpha 90.00 _cell_angle_beta 97.458(6) _cell_angle_gamma 90.00 _cell_volume 1351.82(15) _cell_formula_units_Z 4 _cell_measurement_temperature 213(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.775 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 728 _exptl_absorpt_coefficient_mu 3.210 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.5661 _exptl_absorpt_correction_T_max 0.7396 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 213(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 'IPDS2 diffractometer (Fa. STOE)' _diffrn_measurement_method Omega-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3233 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0212 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 5.31 _diffrn_reflns_theta_max 27.99 _reflns_number_total 3233 _reflns_number_gt 2775 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'IPDS2 software (Fa. STOE)' _computing_cell_refinement 'IPDS2 software (Fa. STOE)' _computing_data_reduction 'IPDS2 software (Fa. STOE)' _computing_structure_solution ? _computing_structure_refinement ? _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0596P)^2^+0.8398P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens ddifmap _refine_ls_hydrogen_treatment refxyz _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0113(17) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3233 _refine_ls_number_parameters 234 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0435 _refine_ls_R_factor_gt 0.0355 _refine_ls_wR_factor_ref 0.1019 _refine_ls_wR_factor_gt 0.0994 _refine_ls_goodness_of_fit_ref 1.139 _refine_ls_restrained_S_all 1.139 _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 C1 C 0.6508(4) 0.5535(3) -0.1062(2) 0.0226(6) Uani 1 1 d . . . C2 C 0.6398(4) 0.6660(3) -0.0559(2) 0.0224(6) Uani 1 1 d . . . C3 C 0.7016(3) 0.6733(3) 0.0431(2) 0.0210(6) Uani 1 1 d . . . C4 C 0.7183(4) 0.7766(3) 0.1086(2) 0.0254(6) Uani 1 1 d . . . C5 C 0.6997(4) 0.8783(3) 0.0363(3) 0.0268(6) Uani 1 1 d . . . C6 C 0.5598(4) 0.8669(3) -0.0461(3) 0.0283(7) Uani 1 1 d . . . C7 C 0.5722(4) 0.7652(3) -0.1168(3) 0.0293(7) Uani 1 1 d . . . C8 C 0.7556(3) 0.3669(2) -0.0391(2) 0.0194(5) Uani 1 1 d . . . C9 C 0.7212(4) 0.3161(3) -0.1366(2) 0.0236(6) Uani 1 1 d . . . C10 C 0.7673(4) 0.2063(3) -0.1469(2) 0.0272(6) Uani 1 1 d . . . C11 C 0.8421(4) 0.1496(3) -0.0608(2) 0.0251(6) Uani 1 1 d . . . C12 C 0.8637(3) 0.2083(2) 0.0321(2) 0.0202(5) Uani 1 1 d . . . N1 N 0.7207(3) 0.4799(2) -0.02332(18) 0.0199(5) Uani 1 1 d . . . N2 N 0.8244(3) 0.3139(2) 0.04548(19) 0.0197(5) Uani 1 1 d . . . O1 O 0.9413(2) 0.55270(19) 0.11025(17) 0.0244(5) Uani 1 1 d . . . O2 O 0.7028(3) 0.5039(2) 0.17311(17) 0.0285(5) Uani 1 1 d . . . O3 O 0.7280(3) 0.55778(19) -0.19375(17) 0.0257(5) Uani 1 1 d . . . O4 O 0.8664(3) 0.6240(2) -0.1666(2) 0.0299(5) Uani 1 1 d . . . S1 S 0.77805(8) 0.54529(6) 0.08938(5) 0.01856(17) Uani 1 1 d . . . Br1 Br 0.95571(4) 0.13310(2) 0.15491(2) 0.02499(13) Uani 1 1 d . . . H1 H 0.541(4) 0.524(4) -0.143(3) 0.027(10) Uiso 1 1 d . . . H4 H 0.937(5) 0.572(4) -0.149(3) 0.028(10) Uiso 1 1 d . . . H4A H 0.643(5) 0.774(4) 0.148(4) 0.037(12) Uiso 1 1 d . . . H4B H 0.827(5) 0.768(4) 0.159(4) 0.041(12) Uiso 1 1 d . . . H5A H 0.682(5) 0.949(4) 0.081(4) 0.040(12) Uiso 1 1 d . . . H5B H 0.784(6) 0.885(4) 0.005(4) 0.043(13) Uiso 1 1 d . . . H6A H 0.548(4) 0.936(3) -0.093(3) 0.024(9) Uiso 1 1 d . . . H6B H 0.463(5) 0.860(3) -0.005(3) 0.029(10) Uiso 1 1 d . . . H7A H 0.638(5) 0.779(3) -0.170(3) 0.027(10) Uiso 1 1 d . . . H7B H 0.483(4) 0.744(3) -0.159(3) 0.023(9) Uiso 1 1 d . . . H9 H 0.671(5) 0.352(3) -0.194(3) 0.026(10) Uiso 1 1 d . . . H10 H 0.764(5) 0.165(4) -0.213(3) 0.030(10) Uiso 1 1 d . . . H11 H 0.883(4) 0.077(3) -0.066(3) 0.016(8) Uiso 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 C1 0.0306(15) 0.0178(13) 0.0176(12) 0.0002(10) -0.0037(11) 0.0031(11) C2 0.0291(15) 0.0189(14) 0.0181(13) -0.0008(11) -0.0015(11) 0.0044(11) C3 0.0262(14) 0.0184(13) 0.0174(13) 0.0012(10) -0.0004(10) 0.0041(11) C4 0.0364(17) 0.0202(15) 0.0190(13) -0.0030(11) 0.0012(12) 0.0034(12) C5 0.0358(17) 0.0188(14) 0.0255(15) -0.0005(12) 0.0031(13) 0.0026(13) C6 0.0382(18) 0.0199(14) 0.0257(15) 0.0004(12) 0.0001(13) 0.0093(13) C7 0.0397(18) 0.0251(16) 0.0210(14) 0.0004(12) -0.0048(13) 0.0097(14) C8 0.0222(13) 0.0174(13) 0.0180(12) -0.0016(10) 0.0001(10) -0.0017(11) C9 0.0313(15) 0.0216(15) 0.0163(13) 0.0008(11) -0.0032(11) -0.0028(12) C10 0.0394(18) 0.0211(15) 0.0196(14) -0.0036(11) -0.0019(12) -0.0030(13) C11 0.0339(16) 0.0164(14) 0.0242(14) -0.0003(11) 0.0005(12) -0.0012(12) C12 0.0245(14) 0.0166(13) 0.0193(12) 0.0015(10) 0.0022(10) 0.0004(11) N1 0.0287(12) 0.0145(11) 0.0145(10) 0.0000(9) -0.0046(9) 0.0014(9) N2 0.0236(12) 0.0168(11) 0.0183(11) 0.0014(9) 0.0009(9) 0.0005(9) O1 0.0249(11) 0.0222(11) 0.0244(10) -0.0024(8) -0.0032(8) 0.0003(8) O2 0.0338(12) 0.0288(12) 0.0232(10) 0.0043(9) 0.0041(9) -0.0006(10) O3 0.0330(12) 0.0236(11) 0.0197(10) 0.0000(8) 0.0003(9) -0.0004(9) O4 0.0277(12) 0.0282(12) 0.0333(12) 0.0028(10) 0.0016(9) -0.0014(10) S1 0.0235(4) 0.0173(3) 0.0140(3) -0.0004(2) -0.0013(2) 0.0013(2) Br1 0.0355(2) 0.01792(17) 0.02041(17) 0.00326(11) -0.00063(11) 0.00327(12) _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 C1 O3 1.396(4) . ? C1 N1 1.459(4) . ? C1 C2 1.502(4) . ? C1 H1 1.08(4) . ? C2 C3 1.326(4) . ? C2 C7 1.503(4) . ? C3 C4 1.493(4) . ? C3 S1 1.745(3) . ? C4 C5 1.529(4) . ? C4 H4A 0.89(5) . ? C4 H4B 1.09(5) . ? C5 C6 1.530(5) . ? C5 H5A 1.05(5) . ? C5 H5B 0.90(5) . ? C6 C7 1.532(5) . ? C6 H6A 1.02(4) . ? C6 H6B 1.07(4) . ? C7 H7A 0.98(4) . ? C7 H7B 0.93(4) . ? C8 N2 1.338(4) . ? C8 C9 1.397(4) . ? C8 N1 1.405(4) . ? C9 C10 1.384(5) . ? C9 H9 0.92(4) . ? C10 C11 1.394(4) . ? C10 H10 0.98(4) . ? C11 C12 1.382(4) . ? C11 H11 0.94(4) . ? C12 N2 1.326(4) . ? C12 Br1 1.911(3) . ? N1 S1 1.672(2) . ? O1 S1 1.435(2) . ? O2 S1 1.430(2) . ? O3 O4 1.460(3) . ? O4 H4 0.89(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 O3 C1 N1 114.4(3) . . ? O3 C1 C2 112.6(3) . . ? N1 C1 C2 105.4(2) . . ? O3 C1 H1 99(2) . . ? N1 C1 H1 113(2) . . ? C2 C1 H1 112(2) . . ? C3 C2 C1 115.8(3) . . ? C3 C2 C7 122.7(3) . . ? C1 C2 C7 121.4(3) . . ? C2 C3 C4 126.8(3) . . ? C2 C3 S1 111.5(2) . . ? C4 C3 S1 121.6(2) . . ? C3 C4 C5 108.3(2) . . ? C3 C4 H4A 105(3) . . ? C5 C4 H4A 110(3) . . ? C3 C4 H4B 106(3) . . ? C5 C4 H4B 117(3) . . ? H4A C4 H4B 109(4) . . ? C4 C5 C6 111.6(3) . . ? C4 C5 H5A 108(3) . . ? C6 C5 H5A 107(3) . . ? C4 C5 H5B 108(3) . . ? C6 C5 H5B 110(3) . . ? H5A C5 H5B 112(4) . . ? C5 C6 C7 111.8(3) . . ? C5 C6 H6A 111(2) . . ? C7 C6 H6A 107(2) . . ? C5 C6 H6B 107(2) . . ? C7 C6 H6B 111(2) . . ? H6A C6 H6B 109(3) . . ? C2 C7 C6 111.5(3) . . ? C2 C7 H7A 106(2) . . ? C6 C7 H7A 113(2) . . ? C2 C7 H7B 110(3) . . ? C6 C7 H7B 116(2) . . ? H7A C7 H7B 100(3) . . ? N2 C8 C9 123.6(3) . . ? N2 C8 N1 114.9(2) . . ? C9 C8 N1 121.5(3) . . ? C10 C9 C8 117.8(3) . . ? C10 C9 H9 118(3) . . ? C8 C9 H9 124(3) . . ? C9 C10 C11 119.9(3) . . ? C9 C10 H10 125(3) . . ? C11 C10 H10 114(3) . . ? C12 C11 C10 116.4(3) . . ? C12 C11 H11 121(2) . . ? C10 C11 H11 122(2) . . ? N2 C12 C11 125.9(3) . . ? N2 C12 Br1 115.4(2) . . ? C11 C12 Br1 118.6(2) . . ? C8 N1 C1 123.5(2) . . ? C8 N1 S1 121.83(19) . . ? C1 N1 S1 114.21(19) . . ? C12 N2 C8 116.3(3) . . ? C1 O3 O4 107.9(2) . . ? O3 O4 H4 103(3) . . ? O2 S1 O1 115.70(14) . . ? O2 S1 N1 112.33(14) . . ? O1 S1 N1 112.08(13) . . ? O2 S1 C3 111.43(15) . . ? O1 S1 C3 110.19(14) . . ? N1 S1 C3 92.87(13) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O4 H4 O1 0.89(5) 1.87(5) 2.747(3) 170(4) 3_765 _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.99 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 1.134 _refine_diff_density_min -0.725 _refine_diff_density_rms 0.094