# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email chmyyy@nus.edu.sg _publ_contact_author_name 'Ying-Yeung Yeung' loop_ _publ_author_name 'Jie Chen' 'Ling Zhou' 'Ying-Yeung Yeung' data_b668 _database_code_depnum_ccdc_archive 'CCDC 859894' #TrackingRef 'web_deposit_cif_file_0_ChongKiatTan_1328416711.B668.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H15 Br N2 O4 S' _chemical_formula_weight 411.27 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 Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 7.5614(5) _cell_length_b 11.1691(7) _cell_length_c 20.0521(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1693.48(19) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 3427 _cell_measurement_theta_min 2.73 _cell_measurement_theta_max 24.81 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.60 _exptl_crystal_size_min 0.34 _exptl_crystal_density_meas 'Not measured' _exptl_crystal_density_diffrn 1.613 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 832 _exptl_absorpt_coefficient_mu 2.573 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.3074 _exptl_absorpt_correction_T_max 0.4749 _exptl_absorpt_process_details 'Sadabs, (Sheldrick 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(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 11943 _diffrn_reflns_av_R_equivalents 0.0438 _diffrn_reflns_av_sigmaI/netI 0.0518 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.03 _diffrn_reflns_theta_max 27.49 _reflns_number_total 3889 _reflns_number_gt 3096 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^)+(0.0325P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.009(9) _refine_ls_number_reflns 3889 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0484 _refine_ls_R_factor_gt 0.0348 _refine_ls_wR_factor_ref 0.0764 _refine_ls_wR_factor_gt 0.0726 _refine_ls_goodness_of_fit_ref 0.954 _refine_ls_restrained_S_all 0.954 _refine_ls_shift/su_max 0.001 _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 Br1 Br 1.00354(5) 0.71374(3) 0.199090(13) 0.05673(11) Uani 1 1 d . . . S1 S 0.49734(10) 0.62991(5) 0.28565(3) 0.03340(13) Uani 1 1 d . . . O1 O 0.4258(2) 0.51609(17) 0.30393(10) 0.0454(5) Uani 1 1 d . . . O2 O 0.4101(2) 0.73792(17) 0.30590(10) 0.0443(5) Uani 1 1 d . . . O3 O 0.6653(7) 0.5553(3) -0.03486(14) 0.1296(16) Uani 1 1 d . . . O4 O 0.5330(8) 0.7235(3) -0.03924(14) 0.163(2) Uani 1 1 d . . . N1 N 0.6962(3) 0.63463(19) 0.31520(10) 0.0344(5) Uani 1 1 d . . . N2 N 0.5892(6) 0.6385(4) -0.00927(16) 0.0973(14) Uani 1 1 d . . . C1 C 0.7962(3) 0.7484(2) 0.31720(13) 0.0340(6) Uani 1 1 d . . . H1 H 0.7478 0.8058 0.2844 0.041 Uiso 1 1 calc R . . C2 C 0.9824(4) 0.7088(2) 0.29675(12) 0.0425(6) Uani 1 1 d . . . H2 H 1.0733 0.7597 0.3181 0.051 Uiso 1 1 calc R . . C3 C 0.9938(4) 0.5805(2) 0.32216(14) 0.0476(6) Uani 1 1 d . . . H3A H 1.0861 0.5358 0.2986 0.057 Uiso 1 1 calc R . . H3B H 1.0186 0.5787 0.3701 0.057 Uiso 1 1 calc R . . C4 C 0.8133(3) 0.5298(2) 0.30737(14) 0.0406(7) Uani 1 1 d . . . H4A H 0.8074 0.4978 0.2619 0.049 Uiso 1 1 calc R . . H4B H 0.7823 0.4664 0.3390 0.049 Uiso 1 1 calc R . . C5 C 0.7984(3) 0.8037(2) 0.38667(13) 0.0380(6) Uani 1 1 d . . . C6 C 0.8764(5) 0.9148(3) 0.39465(16) 0.0569(8) Uani 1 1 d . . . H6 H 0.9242 0.9542 0.3574 0.068 Uiso 1 1 calc R . . C7 C 0.8851(6) 0.9686(3) 0.45653(19) 0.0717(11) Uani 1 1 d . . . H7 H 0.9391 1.0440 0.4609 0.086 Uiso 1 1 calc R . . C8 C 0.8164(5) 0.9139(4) 0.51133(18) 0.0699(10) Uani 1 1 d . . . H8 H 0.8231 0.9507 0.5534 0.084 Uiso 1 1 calc R . . C9 C 0.7374(5) 0.8047(4) 0.50419(16) 0.0671(10) Uani 1 1 d . . . H9 H 0.6884 0.7666 0.5417 0.081 Uiso 1 1 calc R . . C10 C 0.7284(4) 0.7490(3) 0.44214(15) 0.0496(8) Uani 1 1 d . . . H10 H 0.6742 0.6736 0.4382 0.060 Uiso 1 1 calc R . . C11 C 0.5162(4) 0.6317(2) 0.19782(11) 0.0344(5) Uani 1 1 d . . . C12 C 0.5486(4) 0.5258(2) 0.16389(14) 0.0435(8) Uani 1 1 d . . . H12 H 0.5528 0.4527 0.1870 0.052 Uiso 1 1 calc R . . C13 C 0.5746(5) 0.5288(3) 0.09612(16) 0.0576(9) Uani 1 1 d . . . H13 H 0.5997 0.4581 0.0725 0.069 Uiso 1 1 calc R . . C14 C 0.5634(5) 0.6361(3) 0.06356(15) 0.0586(9) Uani 1 1 d . . . C15 C 0.5274(5) 0.7424(3) 0.09639(16) 0.0621(9) Uani 1 1 d . . . H15 H 0.5189 0.8148 0.0727 0.075 Uiso 1 1 calc R . . C16 C 0.5045(5) 0.7399(2) 0.16403(13) 0.0473(6) Uani 1 1 d . . . H16 H 0.4810 0.8110 0.1875 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 Br1 0.05597(18) 0.0725(2) 0.04170(16) -0.00599(13) 0.01705(17) -0.0118(2) S1 0.0257(3) 0.0326(3) 0.0419(3) -0.0011(2) 0.0021(4) -0.0015(4) O1 0.0360(10) 0.0408(11) 0.0594(13) 0.0041(9) 0.0060(9) -0.0061(8) O2 0.0333(9) 0.0434(11) 0.0563(13) -0.0067(9) 0.0045(8) 0.0073(9) O3 0.231(5) 0.107(3) 0.0499(17) -0.0240(18) 0.022(2) 0.006(3) O4 0.332(7) 0.109(3) 0.0472(16) 0.0195(16) -0.010(3) 0.017(4) N1 0.0298(11) 0.0352(12) 0.0382(12) -0.0021(10) 0.0021(9) 0.0007(10) N2 0.169(4) 0.078(2) 0.0448(18) -0.0012(19) -0.002(2) -0.018(3) C1 0.0295(12) 0.0386(14) 0.0338(14) -0.0003(11) 0.0026(11) -0.0043(11) C2 0.0298(13) 0.0609(16) 0.0369(13) -0.0070(11) -0.0008(12) -0.0091(15) C3 0.0317(13) 0.0600(16) 0.0511(15) 0.0011(13) -0.0022(17) 0.0075(18) C4 0.0370(15) 0.0397(15) 0.0451(17) 0.0027(13) -0.0007(13) 0.0055(12) C5 0.0327(13) 0.0442(16) 0.0372(14) -0.0035(13) 0.0002(11) 0.0025(12) C6 0.067(2) 0.0527(19) 0.0511(19) -0.0053(16) 0.0014(17) -0.0152(17) C7 0.083(3) 0.061(2) 0.071(3) -0.0260(19) -0.007(2) -0.013(2) C8 0.071(2) 0.087(3) 0.051(2) -0.026(2) -0.0052(19) 0.005(2) C9 0.074(2) 0.086(3) 0.042(2) -0.008(2) 0.0101(17) 0.002(2) C10 0.0579(18) 0.0515(19) 0.0394(16) -0.0024(14) 0.0084(14) -0.0012(16) C11 0.0296(13) 0.0322(12) 0.0413(13) -0.0017(10) -0.0053(14) -0.0032(13) C12 0.056(2) 0.0309(14) 0.0440(16) -0.0034(11) -0.0086(13) -0.0024(13) C13 0.081(2) 0.0430(17) 0.0490(18) -0.0130(14) -0.0091(16) -0.0033(16) C14 0.084(3) 0.055(2) 0.0374(16) -0.0012(15) -0.0083(15) -0.0080(17) C15 0.093(3) 0.0411(15) 0.0525(18) 0.0114(13) -0.013(2) -0.006(2) C16 0.0620(17) 0.0358(13) 0.0439(15) -0.0029(11) 0.0006(18) 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 Br1 C2 1.966(2) . ? S1 O1 1.429(2) . ? S1 O2 1.4335(19) . ? S1 N1 1.617(2) . ? S1 C11 1.767(2) . ? O3 N2 1.208(5) . ? O4 N2 1.201(5) . ? N1 C4 1.476(3) . ? N1 C1 1.479(3) . ? N2 C14 1.474(4) . ? C1 C5 1.524(4) . ? C1 C2 1.531(4) . ? C2 C3 1.523(4) . ? C3 C4 1.507(4) . ? C5 C10 1.375(4) . ? C5 C6 1.383(4) . ? C6 C7 1.380(4) . ? C7 C8 1.360(5) . ? C8 C9 1.366(5) . ? C9 C10 1.393(4) . ? C11 C12 1.387(4) . ? C11 C16 1.388(3) . ? C12 C13 1.373(4) . ? C13 C14 1.368(5) . ? C14 C15 1.384(5) . ? C15 C16 1.368(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 O1 S1 O2 120.12(11) . . ? O1 S1 N1 106.69(11) . . ? O2 S1 N1 107.25(11) . . ? O1 S1 C11 107.22(12) . . ? O2 S1 C11 108.05(12) . . ? N1 S1 C11 106.85(12) . . ? C4 N1 C1 112.2(2) . . ? C4 N1 S1 119.53(17) . . ? C1 N1 S1 120.90(17) . . ? O4 N2 O3 124.4(4) . . ? O4 N2 C14 117.6(4) . . ? O3 N2 C14 118.0(4) . . ? N1 C1 C5 112.3(2) . . ? N1 C1 C2 102.4(2) . . ? C5 C1 C2 110.6(2) . . ? C3 C2 C1 103.5(2) . . ? C3 C2 Br1 110.82(18) . . ? C1 C2 Br1 109.49(17) . . ? C4 C3 C2 103.7(2) . . ? N1 C4 C3 102.9(2) . . ? C10 C5 C6 118.0(3) . . ? C10 C5 C1 123.7(3) . . ? C6 C5 C1 118.3(3) . . ? C7 C6 C5 121.0(3) . . ? C8 C7 C6 120.8(4) . . ? C7 C8 C9 118.9(3) . . ? C8 C9 C10 120.9(3) . . ? C5 C10 C9 120.3(3) . . ? C12 C11 C16 121.0(2) . . ? C12 C11 S1 119.59(18) . . ? C16 C11 S1 119.41(18) . . ? C13 C12 C11 119.3(3) . . ? C14 C13 C12 119.0(3) . . ? C13 C14 C15 122.5(3) . . ? C13 C14 N2 118.7(3) . . ? C15 C14 N2 118.8(3) . . ? C16 C15 C14 118.6(3) . . ? C15 C16 C11 119.6(2) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.484 _refine_diff_density_min -0.273 _refine_diff_density_rms 0.057 data_b625 _database_code_depnum_ccdc_archive 'CCDC 859895' #TrackingRef 'web_deposit_cif_file_0_ChongKiatTan_1327919630.B625.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H13 Br N2 O4 S2' _chemical_formula_weight 417.29 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 ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' _cell_length_a 7.4711(7) _cell_length_b 11.1765(10) _cell_length_c 19.4619(17) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1625.1(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.706 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 840 _exptl_absorpt_coefficient_mu 2.807 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 11487 _diffrn_reflns_av_R_equivalents 0.0302 _diffrn_reflns_av_sigmaI/netI 0.0476 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3714 _reflns_number_gt 3512 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0410P)^2^+0.8000P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.028(7) _refine_ls_number_reflns 3714 _refine_ls_number_parameters 273 _refine_ls_number_restraints 172 _refine_ls_R_factor_all 0.0292 _refine_ls_R_factor_gt 0.0269 _refine_ls_wR_factor_ref 0.0656 _refine_ls_wR_factor_gt 0.0646 _refine_ls_goodness_of_fit_ref 0.833 _refine_ls_restrained_S_all 0.851 _refine_ls_shift/su_max 0.002 _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 O3 O 0.643(5) 0.4017(10) 1.0445(6) 0.052(4) Uani 0.65(2) 1 d PDU A 1 O4 O 0.636(2) 0.2081(4) 1.0404(4) 0.045(2) Uani 0.65(2) 1 d PDU A 1 S1 S 0.86297(11) 0.07771(7) 0.49586(4) 0.0297(2) Uani 0.9585(19) 1 d PDU B 1 C5 C 0.8325(4) 0.2137(3) 0.60037(14) 0.0219(4) Uani 0.9585(19) 1 d PDU B 1 C6 C 0.8109(4) 0.2881(3) 0.54160(14) 0.0227(4) Uani 0.9585(19) 1 d PDU B 1 H6 H 0.7906 0.3719 0.5441 0.027 Uiso 0.9585(19) 1 calc PR B 1 C7 C 0.8224(4) 0.2267(3) 0.48158(15) 0.0246(4) Uani 0.9585(19) 1 d PDU B 1 H7 H 0.8097 0.2617 0.4374 0.029 Uiso 0.9585(19) 1 calc PR B 1 C8 C 0.8622(4) 0.0972(3) 0.58301(16) 0.0236(4) Uani 0.9585(19) 1 d PDU B 1 H8 H 0.8803 0.0346 0.6153 0.028 Uiso 0.9585(19) 1 calc PR B 1 O3A O 0.667(10) 0.393(2) 1.0483(11) 0.051(4) Uani 0.35(2) 1 d PDU A 2 O4A O 0.563(3) 0.2131(10) 1.0390(8) 0.045(2) Uani 0.35(2) 1 d PDU A 2 S1A S 0.822(3) 0.162(2) 0.4789(8) 0.0273(5) Uani 0.0415(19) 1 d PDU B 2 C5A C 0.843(6) 0.206(5) 0.6052(12) 0.0229(4) Uani 0.0415(19) 1 d PDU B 2 C6A C 0.936(6) 0.100(4) 0.5957(13) 0.0235(4) Uani 0.0415(19) 1 d PDU B 2 H6A H 0.9913 0.0590 0.6327 0.028 Uiso 0.0415(19) 1 calc PR B 2 C7A C 0.942(6) 0.058(3) 0.5294(17) 0.0256(4) Uani 0.0415(19) 1 d PDU B 2 H7A H 0.9999 -0.0129 0.5138 0.031 Uiso 0.0415(19) 1 calc PR B 2 C8A C 0.768(6) 0.257(4) 0.5489(19) 0.0230(4) Uani 0.0415(19) 1 d PDU B 2 H8A H 0.7011 0.3295 0.5474 0.028 Uiso 0.0415(19) 1 calc PR B 2 Br1 Br 1.03757(3) 0.29690(2) 0.796035(12) 0.01993(8) Uani 1 1 d . . . S2 S 0.50782(7) 0.34282(5) 0.71181(3) 0.01307(12) Uani 1 1 d . . . O1 O 0.4447(2) 0.22864(14) 0.68798(9) 0.0172(4) Uani 1 1 d . . . O2 O 0.4093(2) 0.44948(15) 0.69643(10) 0.0181(4) Uani 1 1 d . . . N1 N 0.7072(3) 0.36121(18) 0.68121(11) 0.0142(4) Uani 1 1 d . B . N2 N 0.6175(4) 0.3074(2) 1.01414(13) 0.0385(7) Uani 1 1 d D . . C1 C 0.8023(3) 0.4748(2) 0.69440(14) 0.0165(5) Uani 1 1 d . . . H1A H 0.7916 0.4992 0.7431 0.020 Uiso 1 1 calc R . . H1B H 0.7564 0.5399 0.6647 0.020 Uiso 1 1 calc R . . C2 C 0.9954(3) 0.4430(2) 0.67616(13) 0.0184(5) Uani 1 1 d . . . H2A H 1.0182 0.4544 0.6265 0.022 Uiso 1 1 calc R . . H2B H 1.0810 0.4923 0.7027 0.022 Uiso 1 1 calc R . . C3 C 1.0099(3) 0.3114(2) 0.69599(12) 0.0175(5) Uani 1 1 d . B . H3 H 1.1114 0.2719 0.6714 0.021 Uiso 1 1 calc R . . C4 C 0.8296(3) 0.2576(2) 0.67394(13) 0.0152(5) Uani 1 1 d D . . H4 H 0.7937 0.1917 0.7058 0.018 Uiso 1 1 calc R B 1 C9 C 0.5307(3) 0.3344(2) 0.80195(12) 0.0142(4) Uani 1 1 d . . . C10 C 0.5551(4) 0.2226(2) 0.83141(13) 0.0189(5) Uani 1 1 d . A . H10 H 0.5536 0.1527 0.8037 0.023 Uiso 1 1 calc R . . C11 C 0.5816(4) 0.2142(3) 0.90134(14) 0.0245(6) Uani 1 1 d . . . H11 H 0.5962 0.1385 0.9228 0.029 Uiso 1 1 calc R A . C12 C 0.5864(4) 0.3182(2) 0.93935(13) 0.0242(6) Uani 1 1 d . A . C13 C 0.5615(4) 0.4301(2) 0.91118(14) 0.0250(6) Uani 1 1 d . . . H13 H 0.5644 0.4997 0.9392 0.030 Uiso 1 1 calc R A . C14 C 0.5322(4) 0.4385(2) 0.84105(13) 0.0193(5) Uani 1 1 d . A . H14 H 0.5134 0.5142 0.8200 0.023 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 O3 0.099(10) 0.034(2) 0.0209(17) -0.0075(14) -0.016(2) 0.012(4) O4 0.084(7) 0.0339(15) 0.0181(13) 0.0086(12) -0.008(4) 0.003(3) S1 0.0385(4) 0.0260(4) 0.0246(4) -0.0122(3) 0.0057(3) -0.0035(3) C5 0.0259(7) 0.0205(7) 0.0191(7) -0.0052(7) 0.0021(6) -0.0010(7) C6 0.0270(8) 0.0213(7) 0.0197(8) -0.0048(7) 0.0014(6) -0.0008(7) C7 0.0301(8) 0.0229(8) 0.0208(8) -0.0056(7) 0.0016(7) -0.0013(7) C8 0.0287(8) 0.0217(7) 0.0203(7) -0.0058(7) 0.0025(7) -0.0018(7) O3A 0.099(10) 0.034(2) 0.0209(18) -0.0074(16) -0.015(2) 0.012(4) O4A 0.084(7) 0.0340(16) 0.0179(14) 0.0085(13) -0.007(4) 0.002(3) S1A 0.0344(9) 0.0246(9) 0.0227(9) -0.0089(9) 0.0035(8) -0.0023(9) C5A 0.0275(8) 0.0213(8) 0.0198(8) -0.0054(7) 0.0021(7) -0.0013(7) C6A 0.0285(8) 0.0216(8) 0.0203(8) -0.0061(8) 0.0025(7) -0.0016(8) C7A 0.0319(8) 0.0231(8) 0.0218(8) -0.0080(8) 0.0035(8) -0.0023(8) C8A 0.0276(8) 0.0215(8) 0.0199(8) -0.0052(8) 0.0018(7) -0.0011(8) Br1 0.02028(12) 0.02281(12) 0.01669(12) 0.00139(10) -0.00313(10) 0.00165(10) S2 0.0127(3) 0.0113(2) 0.0152(3) 0.0002(2) -0.0006(2) -0.0003(2) O1 0.0174(9) 0.0146(9) 0.0196(9) -0.0012(6) -0.0023(7) -0.0025(7) O2 0.0143(8) 0.0152(8) 0.0249(10) 0.0028(7) -0.0014(7) 0.0015(6) N1 0.0131(9) 0.0124(10) 0.0170(10) -0.0006(8) 0.0026(7) 0.0008(8) N2 0.068(2) 0.0296(14) 0.0179(12) -0.0020(11) 0.0019(12) 0.0035(14) C1 0.0140(11) 0.0133(11) 0.0222(13) 0.0018(9) -0.0001(10) -0.0027(9) C2 0.0158(13) 0.0190(12) 0.0204(12) 0.0008(9) 0.0003(9) -0.0018(10) C3 0.0167(11) 0.0225(12) 0.0133(10) 0.0003(9) -0.0006(9) 0.0019(9) C4 0.0160(11) 0.0132(11) 0.0164(12) 0.0008(9) 0.0011(9) 0.0026(10) C9 0.0146(10) 0.0152(10) 0.0127(10) 0.0002(8) 0.0023(10) -0.0009(9) C10 0.0253(13) 0.0128(12) 0.0186(12) -0.0005(9) 0.0021(10) -0.0023(10) C11 0.0378(16) 0.0173(12) 0.0184(12) 0.0030(11) 0.0031(11) -0.0013(12) C12 0.0347(15) 0.0228(14) 0.0150(12) -0.0004(10) 0.0023(10) 0.0007(11) C13 0.0359(16) 0.0196(12) 0.0193(13) -0.0078(10) 0.0027(12) 0.0016(13) C14 0.0240(12) 0.0129(11) 0.0211(12) -0.0014(9) 0.0013(11) 0.0009(11) _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 O3 N2 1.223(4) . ? O4 N2 1.230(4) . ? S1 C8 1.710(3) . ? S1 C7 1.715(3) . ? C5 C8 1.363(4) . ? C5 C6 1.423(4) . ? C5 C4 1.514(4) . ? C6 C7 1.358(4) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? O3A N2 1.225(5) . ? O4A N2 1.228(5) . ? S1A C7A 1.77(2) . ? S1A C8A 1.77(2) . ? C5A C8A 1.361(17) . ? C5A C6A 1.378(18) . ? C5A C4 1.462(16) . ? C6A C7A 1.376(17) . ? C6A H6A 0.9500 . ? C7A H7A 0.9500 . ? C8A H8A 0.9500 . ? Br1 C3 1.965(2) . ? S2 O2 1.4326(18) . ? S2 O1 1.4374(17) . ? S2 N1 1.617(2) . ? S2 C9 1.765(2) . ? N1 C1 1.478(3) . ? N1 C4 1.482(3) . ? N2 C12 1.479(4) . ? C1 C2 1.527(3) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C3 1.525(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.536(3) . ? C3 H3 1.0000 . ? C4 H4 1.0000 . ? C9 C10 1.386(3) . ? C9 C14 1.391(3) . ? C10 C11 1.379(4) . ? C10 H10 0.9500 . ? C11 C12 1.378(4) . ? C11 H11 0.9500 . ? C12 C13 1.379(4) . ? C13 C14 1.386(4) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? 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 C8 S1 C7 92.10(14) . . ? C8 C5 C6 112.2(3) . . ? C8 C5 C4 123.1(3) . . ? C6 C5 C4 124.7(3) . . ? C7 C6 C5 112.9(3) . . ? C7 C6 H6 123.6 . . ? C5 C6 H6 123.6 . . ? C6 C7 S1 111.3(2) . . ? C6 C7 H7 124.4 . . ? S1 C7 H7 124.4 . . ? C5 C8 S1 111.6(2) . . ? C5 C8 H8 124.2 . . ? S1 C8 H8 124.2 . . ? C7A S1A C8A 94.8(10) . . ? C8A C5A C6A 117.5(12) . . ? C8A C5A C4 123(3) . . ? C6A C5A C4 120(3) . . ? C7A C6A C5A 115.9(12) . . ? C7A C6A H6A 122.0 . . ? C5A C6A H6A 122.0 . . ? C6A C7A S1A 106.0(12) . . ? C6A C7A H7A 127.0 . . ? S1A C7A H7A 127.0 . . ? C5A C8A S1A 105.7(12) . . ? C5A C8A H8A 127.2 . . ? S1A C8A H8A 127.2 . . ? O2 S2 O1 120.18(10) . . ? O2 S2 N1 106.89(11) . . ? O1 S2 N1 107.23(11) . . ? O2 S2 C9 107.58(11) . . ? O1 S2 C9 107.75(10) . . ? N1 S2 C9 106.47(11) . . ? C1 N1 C4 113.00(19) . . ? C1 N1 S2 119.23(16) . . ? C4 N1 S2 120.29(16) . . ? O3 N2 O3A 10(5) . . ? O3 N2 O4A 127.0(15) . . ? O3A N2 O4A 123.9(8) . . ? O3 N2 O4 124.0(6) . . ? O3A N2 O4 116.5(18) . . ? O4A N2 O4 25.9(7) . . ? O3 N2 C12 115.4(6) . . ? O3A N2 C12 121.2(11) . . ? O4A N2 C12 113.9(9) . . ? O4 N2 C12 120.0(5) . . ? N1 C1 C2 102.33(19) . . ? N1 C1 H1A 111.3 . . ? C2 C1 H1A 111.3 . . ? N1 C1 H1B 111.3 . . ? C2 C1 H1B 111.3 . . ? H1A C1 H1B 109.2 . . ? C3 C2 C1 103.5(2) . . ? C3 C2 H2A 111.1 . . ? C1 C2 H2A 111.1 . . ? C3 C2 H2B 111.1 . . ? C1 C2 H2B 111.1 . . ? H2A C2 H2B 109.0 . . ? C2 C3 C4 104.14(19) . . ? C2 C3 Br1 109.74(16) . . ? C4 C3 Br1 109.70(16) . . ? C2 C3 H3 111.0 . . ? C4 C3 H3 111.0 . . ? Br1 C3 H3 111.0 . . ? C5A C4 N1 116.2(18) . . ? C5A C4 C5 5.6(19) . . ? N1 C4 C5 110.6(2) . . ? C5A C4 C3 110.5(18) . . ? N1 C4 C3 102.07(19) . . ? C5 C4 C3 112.3(2) . . ? C5A C4 H4 107.0 . . ? N1 C4 H4 110.5 . . ? C5 C4 H4 110.5 . . ? C3 C4 H4 110.5 . . ? C10 C9 C14 121.8(2) . . ? C10 C9 S2 118.17(18) . . ? C14 C9 S2 119.98(18) . . ? C11 C10 C9 119.3(2) . . ? C11 C10 H10 120.4 . . ? C9 C10 H10 120.4 . . ? C12 C11 C10 118.4(2) . . ? C12 C11 H11 120.8 . . ? C10 C11 H11 120.8 . . ? C11 C12 C13 123.3(2) . . ? C11 C12 N2 117.6(2) . . ? C13 C12 N2 119.1(2) . . ? C12 C13 C14 118.3(2) . . ? C12 C13 H13 120.8 . . ? C14 C13 H13 120.8 . . ? C13 C14 C9 118.9(2) . . ? C13 C14 H14 120.5 . . ? C9 C14 H14 120.5 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.641 _refine_diff_density_min -0.314 _refine_diff_density_rms 0.087