# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_2a _database_code_depnum_ccdc_archive 'CCDC 898514' #TrackingRef 'web_deposit_cif_file_0_DanielTay_1346158312.2a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H17 Br N2 O4 S' _chemical_formula_weight 425.30 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) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.588(2) _cell_length_b 10.733(3) _cell_length_c 10.934(3) _cell_angle_alpha 90.00 _cell_angle_beta 102.039(6) _cell_angle_gamma 90.00 _cell_volume 870.9(4) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 922 _cell_measurement_theta_min 2.69 _cell_measurement_theta_max 27.44 _exptl_crystal_description BLOCK _exptl_crystal_colour COLOURLESS _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'Not Measured' _exptl_crystal_density_diffrn 1.622 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 432 _exptl_absorpt_coefficient_mu 2.505 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.3344 _exptl_absorpt_correction_T_max 0.7878 _exptl_absorpt_process_details 'Sadabs, (Sheldrick 2001)' _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 '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 5878 _diffrn_reflns_av_R_equivalents 0.0217 _diffrn_reflns_av_sigmaI/netI 0.0477 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3024 _reflns_number_gt 2905 _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^)+(0.0348P)^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 0.008(7) _refine_ls_number_reflns 3024 _refine_ls_number_parameters 226 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0269 _refine_ls_R_factor_gt 0.0257 _refine_ls_wR_factor_ref 0.0691 _refine_ls_wR_factor_gt 0.0672 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.063 _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 0.70289(3) 0.66103(3) 0.81148(2) 0.02327(9) Uani 1 1 d . . . S1 S 0.65160(8) 0.33251(6) 1.03338(6) 0.01647(14) Uani 1 1 d . . . O1 O 0.4666(2) 0.35196(19) 0.97554(16) 0.0201(4) Uani 1 1 d . . . O2 O 0.7071(3) 0.21227(19) 1.08590(19) 0.0219(4) Uani 1 1 d . . . O3 O 0.8357(3) 0.8142(2) 1.41807(19) 0.0302(5) Uani 1 1 d . . . O4 O 0.9407(3) 0.6669(3) 1.54727(16) 0.0340(4) Uani 1 1 d . . . N1 N 0.7707(3) 0.3738(2) 0.9333(2) 0.0173(4) Uani 1 1 d . . . N2 N 0.8661(3) 0.7036(2) 1.4434(2) 0.0220(5) Uani 1 1 d . . . C1 C 0.6935(4) 0.2753(3) 0.7206(3) 0.0205(6) Uani 1 1 d . . . C2 C 0.6452(4) 0.2836(3) 0.5907(3) 0.0254(7) Uani 1 1 d . . . H2 H 0.6181 0.3623 0.5516 0.030 Uiso 1 1 calc R . . C3 C 0.6369(4) 0.1752(4) 0.5179(3) 0.0339(7) Uani 1 1 d . . . H3 H 0.6035 0.1811 0.4294 0.041 Uiso 1 1 calc R . . C4 C 0.6763(5) 0.0612(4) 0.5727(3) 0.0323(8) Uani 1 1 d . . . H4 H 0.6724 -0.0114 0.5226 0.039 Uiso 1 1 calc R . . C5 C 0.7220(5) 0.0524(3) 0.7020(3) 0.0297(7) Uani 1 1 d . . . H5 H 0.7483 -0.0267 0.7406 0.036 Uiso 1 1 calc R . . C6 C 0.7294(3) 0.1590(4) 0.7752(2) 0.0242(5) Uani 1 1 d . . . H6 H 0.7594 0.1519 0.8637 0.029 Uiso 1 1 calc R . . C7 C 0.6897(3) 0.3938(3) 0.7992(2) 0.0178(5) Uani 1 1 d . . . H7 H 0.5609 0.4186 0.7923 0.021 Uiso 1 1 calc R . . C8 C 0.7887(4) 0.5029(3) 0.7518(2) 0.0193(5) Uani 1 1 d . . . H8 H 0.7555 0.5028 0.6584 0.023 Uiso 1 1 calc R . . C9 C 0.9937(4) 0.4950(3) 0.7905(2) 0.0214(5) Uani 1 1 d . . . H9A H 1.0371 0.4249 0.7459 0.026 Uiso 1 1 calc R . . H9B H 1.0472 0.5727 0.7656 0.026 Uiso 1 1 calc R . . C10 C 1.0558(4) 0.4763(3) 0.9303(3) 0.0214(5) Uani 1 1 d . . . H10A H 1.1886 0.4675 0.9516 0.026 Uiso 1 1 calc R . . H10B H 1.0224 0.5498 0.9753 0.026 Uiso 1 1 calc R . . C11 C 0.9689(3) 0.3606(3) 0.9705(2) 0.0193(5) Uani 1 1 d . . . H11A H 1.0086 0.2862 0.9300 0.023 Uiso 1 1 calc R . . H11B H 1.0053 0.3502 1.0622 0.023 Uiso 1 1 calc R . . C12 C 0.7144(3) 0.4417(2) 1.1565(2) 0.0156(5) Uani 1 1 d . . . C13 C 0.6714(4) 0.5665(3) 1.1330(2) 0.0193(5) Uani 1 1 d . . . H13 H 0.6083 0.5921 1.0526 0.023 Uiso 1 1 calc R . . C14 C 0.7211(3) 0.6533(3) 1.2278(2) 0.0179(5) Uani 1 1 d . . . H14 H 0.6939 0.7392 1.2137 0.021 Uiso 1 1 calc R . . C15 C 0.8112(3) 0.6113(3) 1.3432(2) 0.0175(5) Uani 1 1 d . . . C16 C 0.8559(4) 0.4872(3) 1.3684(2) 0.0231(6) Uani 1 1 d . . . H16 H 0.9184 0.4620 1.4491 0.028 Uiso 1 1 calc R . . C17 C 0.8073(4) 0.4014(3) 1.2735(2) 0.0205(5) Uani 1 1 d . . . H17 H 0.8367 0.3158 1.2877 0.025 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 0.02674(14) 0.01404(12) 0.02752(13) -0.00172(12) 0.00216(9) 0.00378(12) S1 0.0174(3) 0.0113(3) 0.0214(3) -0.0024(2) 0.0055(2) -0.0010(2) O1 0.0170(9) 0.0192(11) 0.0244(9) -0.0037(8) 0.0047(7) -0.0018(8) O2 0.0252(10) 0.0133(9) 0.0279(10) 0.0000(8) 0.0072(8) 0.0021(7) O3 0.0451(13) 0.0168(11) 0.0293(11) -0.0052(9) 0.0095(9) -0.0045(10) O4 0.0534(12) 0.0283(10) 0.0163(8) -0.0024(12) -0.0014(8) -0.0038(15) N1 0.0139(10) 0.0171(11) 0.0209(11) 0.0004(9) 0.0038(8) 0.0018(8) N2 0.0250(11) 0.0200(12) 0.0219(11) -0.0024(9) 0.0068(9) -0.0055(9) C1 0.0154(13) 0.0192(14) 0.0269(14) -0.0063(11) 0.0044(11) -0.0018(11) C2 0.0253(15) 0.0234(15) 0.0256(15) -0.0066(12) 0.0009(12) -0.0017(12) C3 0.0317(14) 0.042(2) 0.0268(13) -0.0137(17) 0.0037(11) -0.0042(17) C4 0.0284(16) 0.0303(18) 0.0381(18) -0.0204(15) 0.0065(13) -0.0026(13) C5 0.0303(17) 0.0154(15) 0.0440(19) -0.0086(13) 0.0091(14) 0.0012(12) C6 0.0240(12) 0.0198(13) 0.0283(12) -0.0035(16) 0.0048(9) 0.0023(15) C7 0.0165(13) 0.0148(13) 0.0213(13) -0.0025(10) 0.0022(10) -0.0005(9) C8 0.0229(13) 0.0145(12) 0.0203(12) -0.0020(10) 0.0038(10) 0.0011(10) C9 0.0218(13) 0.0174(13) 0.0271(13) 0.0003(11) 0.0101(10) 0.0007(11) C10 0.0164(12) 0.0180(14) 0.0284(13) -0.0010(11) 0.0018(10) -0.0001(10) C11 0.0157(12) 0.0192(14) 0.0235(13) 0.0000(11) 0.0053(10) 0.0000(10) C12 0.0147(12) 0.0143(12) 0.0181(11) -0.0026(10) 0.0041(9) 0.0001(10) C13 0.0204(13) 0.0172(13) 0.0194(12) 0.0002(10) 0.0022(10) 0.0022(10) C14 0.0180(10) 0.0134(12) 0.0225(10) -0.0015(12) 0.0047(8) 0.0010(12) C15 0.0175(12) 0.0162(12) 0.0198(12) -0.0012(10) 0.0066(10) -0.0009(10) C16 0.0286(15) 0.0214(15) 0.0186(12) 0.0032(11) 0.0033(11) 0.0023(12) C17 0.0269(14) 0.0120(12) 0.0228(13) 0.0042(10) 0.0053(11) 0.0033(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 Br1 C8 1.977(3) . ? S1 O1 1.4297(19) . ? S1 O2 1.439(2) . ? S1 N1 1.619(2) . ? S1 C12 1.774(3) . ? O3 N2 1.230(3) . ? O4 N2 1.223(3) . ? N1 C11 1.481(3) . ? N1 C7 1.482(3) . ? N2 C15 1.472(3) . ? C1 C6 1.386(5) . ? C1 C2 1.394(4) . ? C1 C7 1.539(4) . ? C2 C3 1.404(5) . ? C3 C4 1.367(6) . ? C4 C5 1.386(5) . ? C5 C6 1.391(5) . ? C7 C8 1.539(4) . ? C8 C9 1.527(4) . ? C9 C10 1.516(4) . ? C10 C11 1.513(4) . ? C12 C13 1.389(4) . ? C12 C17 1.394(3) . ? C13 C14 1.386(4) . ? C14 C15 1.379(3) . ? C15 C16 1.388(4) . ? C16 C17 1.379(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 119.09(12) . . ? O1 S1 N1 107.22(11) . . ? O2 S1 N1 110.91(12) . . ? O1 S1 C12 108.84(11) . . ? O2 S1 C12 106.23(12) . . ? N1 S1 C12 103.44(12) . . ? C11 N1 C7 118.2(2) . . ? C11 N1 S1 117.82(17) . . ? C7 N1 S1 122.21(17) . . ? O4 N2 O3 123.3(3) . . ? O4 N2 C15 118.6(2) . . ? O3 N2 C15 118.1(2) . . ? C6 C1 C2 118.8(3) . . ? C6 C1 C7 121.9(3) . . ? C2 C1 C7 119.0(3) . . ? C1 C2 C3 119.8(3) . . ? C4 C3 C2 120.8(3) . . ? C3 C4 C5 119.6(3) . . ? C4 C5 C6 120.1(3) . . ? C1 C6 C5 120.9(3) . . ? N1 C7 C1 112.4(2) . . ? N1 C7 C8 108.2(2) . . ? C1 C7 C8 111.9(2) . . ? C9 C8 C7 113.9(2) . . ? C9 C8 Br1 110.03(19) . . ? C7 C8 Br1 108.94(18) . . ? C10 C9 C8 111.8(2) . . ? C11 C10 C9 109.8(2) . . ? N1 C11 C10 108.7(2) . . ? C13 C12 C17 121.5(2) . . ? C13 C12 S1 118.7(2) . . ? C17 C12 S1 119.7(2) . . ? C14 C13 C12 119.5(2) . . ? C15 C14 C13 118.0(3) . . ? C14 C15 C16 123.3(3) . . ? C14 C15 N2 118.1(3) . . ? C16 C15 N2 118.6(2) . . ? C17 C16 C15 118.4(2) . . ? C16 C17 C12 119.2(3) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.797 _refine_diff_density_min -0.354 _refine_diff_density_rms 0.073 data_ent_3a _database_code_depnum_ccdc_archive 'CCDC 898515' #TrackingRef 'web_deposit_cif_file_1_DanielTay_1346158312.ent_3a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H18 N2 O5 S' _chemical_formula_weight 362.39 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 14.476(7) _cell_length_b 7.111(4) _cell_length_c 16.113(8) _cell_angle_alpha 90.00 _cell_angle_beta 101.412(9) _cell_angle_gamma 90.00 _cell_volume 1625.9(14) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2165 _cell_measurement_theta_min 2.58 _cell_measurement_theta_max 27.93 _exptl_crystal_description Rod _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'Not Measured' _exptl_crystal_density_diffrn 1.480 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 760 _exptl_absorpt_coefficient_mu 0.231 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8737 _exptl_absorpt_correction_T_max 0.9772 _exptl_absorpt_process_details 'Sadabs, (Sheldrick 2008)' _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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 10087 _diffrn_reflns_av_R_equivalents 0.0599 _diffrn_reflns_av_sigmaI/netI 0.0696 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.73 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3731 _reflns_number_gt 2837 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0983P)^2^+0.1400P] 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 3731 _refine_ls_number_parameters 227 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0862 _refine_ls_R_factor_gt 0.0631 _refine_ls_wR_factor_ref 0.1712 _refine_ls_wR_factor_gt 0.1552 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _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 S1 S 1.14169(5) 0.84972(9) 0.18772(4) 0.0161(2) Uani 1 1 d . . . O1 O 1.11343(14) 0.5568(3) 0.37284(12) 0.0215(4) Uani 1 1 d . . . H1 H 1.1664 0.5227 0.3644 0.032 Uiso 1 1 calc R . . O2 O 1.12889(13) 0.6733(3) 0.14215(11) 0.0190(4) Uani 1 1 d . . . O3 O 1.22980(13) 0.9488(3) 0.19566(12) 0.0220(4) Uani 1 1 d . . . O4 O 0.75248(15) 1.2998(3) 0.00355(13) 0.0308(5) Uani 1 1 d . . . O5 O 0.84785(15) 1.5400(3) 0.02541(13) 0.0260(5) Uani 1 1 d . . . N1 N 1.12185(16) 0.8146(3) 0.28157(13) 0.0172(5) Uani 1 1 d . . . N2 N 0.83063(17) 1.3687(3) 0.02724(14) 0.0218(5) Uani 1 1 d . . . C1 C 1.1380(2) 0.9680(4) 0.34570(17) 0.0200(6) Uani 1 1 d . . . H1A H 1.1698 1.0748 0.3236 0.024 Uiso 1 1 calc R . . H1B H 1.1798 0.9220 0.3979 0.024 Uiso 1 1 calc R . . C2 C 1.0452(2) 1.0349(4) 0.36651(19) 0.0237(6) Uani 1 1 d . . . H2A H 1.0076 1.0991 0.3165 0.028 Uiso 1 1 calc R . . H2B H 1.0583 1.1270 0.4135 0.028 Uiso 1 1 calc R . . C3 C 0.9879(2) 0.8702(4) 0.39208(17) 0.0201(6) Uani 1 1 d . . . H3A H 1.0228 0.8121 0.4449 0.024 Uiso 1 1 calc R . . H3B H 0.9269 0.9171 0.4028 0.024 Uiso 1 1 calc R . . C4 C 0.97018(18) 0.7226(4) 0.32110(16) 0.0177(6) Uani 1 1 d . . . H4A H 0.9358 0.7884 0.2692 0.021 Uiso 1 1 calc R . . C5 C 1.06441(19) 0.6536(4) 0.30071(16) 0.0171(6) Uani 1 1 d . . . H5A H 1.0517 0.5662 0.2512 0.020 Uiso 1 1 calc R . . C6 C 0.91016(19) 0.5532(4) 0.33444(17) 0.0179(6) Uani 1 1 d . . . C7 C 0.87293(19) 0.4403(4) 0.26473(17) 0.0200(6) Uani 1 1 d . . . H7 H 0.8855 0.4716 0.2107 0.024 Uiso 1 1 calc R . . C8 C 0.8178(2) 0.2830(4) 0.27245(18) 0.0248(6) Uani 1 1 d . . . H8 H 0.7933 0.2084 0.2242 0.030 Uiso 1 1 calc R . . C9 C 0.7990(2) 0.2359(4) 0.35184(18) 0.0248(6) Uani 1 1 d . . . H9 H 0.7612 0.1294 0.3578 0.030 Uiso 1 1 calc R . . C10 C 0.83585(19) 0.3457(4) 0.42160(17) 0.0223(6) Uani 1 1 d . . . H10 H 0.8237 0.3130 0.4756 0.027 Uiso 1 1 calc R . . C11 C 0.89078(19) 0.5038(4) 0.41354(17) 0.0202(6) Uani 1 1 d . . . H11 H 0.9151 0.5783 0.4619 0.024 Uiso 1 1 calc R . . C12 C 1.05232(19) 1.0059(4) 0.13537(16) 0.0168(5) Uani 1 1 d . . . C13 C 0.96322(19) 0.9306(4) 0.10314(17) 0.0201(6) Uani 1 1 d . . . H13 H 0.9526 0.7992 0.1064 0.024 Uiso 1 1 calc R . . C14 C 0.8903(2) 1.0494(4) 0.06634(17) 0.0196(6) Uani 1 1 d . . . H14 H 0.8291 1.0013 0.0445 0.024 Uiso 1 1 calc R . . C15 C 0.90949(19) 1.2419(4) 0.06223(16) 0.0183(6) Uani 1 1 d . . . C16 C 0.99765(19) 1.3174(4) 0.09190(16) 0.0190(6) Uani 1 1 d . . . H16 H 1.0085 1.4482 0.0866 0.023 Uiso 1 1 calc R . . C17 C 1.0708(2) 1.1981(4) 0.12989(17) 0.0196(6) Uani 1 1 d . . . H17 H 1.1320 1.2468 0.1515 0.024 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 S1 0.0134(4) 0.0106(3) 0.0241(3) -0.0009(2) 0.0034(2) -0.0017(2) O1 0.0182(11) 0.0173(10) 0.0291(10) 0.0049(8) 0.0052(8) 0.0056(8) O2 0.0194(10) 0.0131(9) 0.0246(9) -0.0032(7) 0.0046(8) -0.0002(7) O3 0.0143(10) 0.0203(11) 0.0318(10) 0.0001(8) 0.0056(8) -0.0053(8) O4 0.0178(11) 0.0269(12) 0.0454(12) 0.0121(10) 0.0007(9) 0.0001(9) O5 0.0321(13) 0.0109(9) 0.0339(11) 0.0002(8) 0.0038(9) 0.0048(8) N1 0.0174(12) 0.0101(11) 0.0239(11) -0.0004(8) 0.0038(9) -0.0008(9) N2 0.0239(14) 0.0170(12) 0.0251(11) 0.0034(9) 0.0063(10) 0.0024(10) C1 0.0186(15) 0.0146(13) 0.0258(13) -0.0056(10) 0.0017(11) -0.0054(10) C2 0.0273(17) 0.0116(13) 0.0322(15) -0.0042(11) 0.0058(12) -0.0004(11) C3 0.0173(14) 0.0145(13) 0.0286(14) -0.0010(11) 0.0045(11) 0.0012(11) C4 0.0139(13) 0.0124(12) 0.0264(13) 0.0012(10) 0.0030(10) 0.0017(10) C5 0.0179(14) 0.0107(12) 0.0233(13) -0.0002(10) 0.0055(10) -0.0016(10) C6 0.0124(13) 0.0124(13) 0.0283(14) 0.0016(10) 0.0028(10) 0.0032(10) C7 0.0136(14) 0.0180(14) 0.0279(14) 0.0018(11) 0.0032(11) 0.0015(11) C8 0.0187(15) 0.0210(15) 0.0333(15) -0.0034(12) 0.0022(12) -0.0033(12) C9 0.0178(15) 0.0195(15) 0.0373(15) 0.0026(12) 0.0054(12) -0.0035(11) C10 0.0151(14) 0.0250(15) 0.0272(14) 0.0064(11) 0.0050(11) 0.0024(11) C11 0.0155(14) 0.0189(14) 0.0252(13) 0.0011(11) 0.0019(11) 0.0030(11) C12 0.0173(14) 0.0105(12) 0.0229(12) 0.0004(10) 0.0042(10) -0.0012(10) C13 0.0196(15) 0.0125(13) 0.0276(14) -0.0007(11) 0.0035(11) -0.0045(11) C14 0.0169(14) 0.0156(14) 0.0255(13) 0.0004(10) 0.0022(11) -0.0064(10) C15 0.0191(14) 0.0147(13) 0.0210(12) 0.0013(10) 0.0041(10) 0.0024(11) C16 0.0226(15) 0.0091(12) 0.0258(13) -0.0016(10) 0.0056(11) -0.0031(10) C17 0.0186(14) 0.0125(13) 0.0273(13) -0.0017(10) 0.0032(11) -0.0037(10) _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 O3 1.441(2) . ? S1 O2 1.447(2) . ? S1 N1 1.614(2) . ? S1 C12 1.785(3) . ? O1 C5 1.415(3) . ? O1 H1 0.8400 . ? O4 N2 1.223(3) . ? O5 N2 1.245(3) . ? N1 C5 1.482(3) . ? N1 C1 1.489(3) . ? N2 C15 1.476(4) . ? C1 C2 1.524(4) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C3 1.538(4) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.536(4) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C6 1.525(4) . ? C4 C5 1.545(4) . ? C4 H4A 1.0000 . ? C5 H5A 1.0000 . ? C6 C7 1.399(4) . ? C6 C11 1.403(4) . ? C7 C8 1.393(4) . ? C7 H7 0.9500 . ? C8 C9 1.401(4) . ? C8 H8 0.9500 . ? C9 C10 1.386(4) . ? C9 H9 0.9500 . ? C10 C11 1.398(4) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? C12 C13 1.398(4) . ? C12 C17 1.399(4) . ? C13 C14 1.389(4) . ? C13 H13 0.9500 . ? C14 C15 1.401(4) . ? C14 H14 0.9500 . ? C15 C16 1.380(4) . ? C16 C17 1.400(4) . ? C16 H16 0.9500 . ? C17 H17 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 O3 S1 O2 119.43(12) . . ? O3 S1 N1 108.14(12) . . ? O2 S1 N1 108.22(11) . . ? O3 S1 C12 106.49(13) . . ? O2 S1 C12 106.94(12) . . ? N1 S1 C12 107.00(12) . . ? C5 O1 H1 109.5 . . ? C5 N1 C1 116.0(2) . . ? C5 N1 S1 121.72(17) . . ? C1 N1 S1 120.27(18) . . ? O4 N2 O5 124.2(2) . . ? O4 N2 C15 118.2(2) . . ? O5 N2 C15 117.6(2) . . ? N1 C1 C2 110.9(2) . . ? N1 C1 H1A 109.5 . . ? C2 C1 H1A 109.5 . . ? N1 C1 H1B 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 108.0 . . ? C1 C2 C3 111.5(2) . . ? C1 C2 H2A 109.3 . . ? C3 C2 H2A 109.3 . . ? C1 C2 H2B 109.3 . . ? C3 C2 H2B 109.3 . . ? H2A C2 H2B 108.0 . . ? C4 C3 C2 109.9(2) . . ? C4 C3 H3A 109.7 . . ? C2 C3 H3A 109.7 . . ? C4 C3 H3B 109.7 . . ? C2 C3 H3B 109.7 . . ? H3A C3 H3B 108.2 . . ? C6 C4 C3 116.8(2) . . ? C6 C4 C5 109.3(2) . . ? C3 C4 C5 110.6(2) . . ? C6 C4 H4A 106.5 . . ? C3 C4 H4A 106.5 . . ? C5 C4 H4A 106.5 . . ? O1 C5 N1 109.6(2) . . ? O1 C5 C4 107.5(2) . . ? N1 C5 C4 110.8(2) . . ? O1 C5 H5A 109.7 . . ? N1 C5 H5A 109.7 . . ? C4 C5 H5A 109.7 . . ? C7 C6 C11 118.1(3) . . ? C7 C6 C4 118.7(2) . . ? C11 C6 C4 123.2(2) . . ? C8 C7 C6 121.7(3) . . ? C8 C7 H7 119.2 . . ? C6 C7 H7 119.2 . . ? C7 C8 C9 119.5(3) . . ? C7 C8 H8 120.3 . . ? C9 C8 H8 120.3 . . ? C10 C9 C8 119.5(3) . . ? C10 C9 H9 120.2 . . ? C8 C9 H9 120.2 . . ? C9 C10 C11 120.8(3) . . ? C9 C10 H10 119.6 . . ? C11 C10 H10 119.6 . . ? C10 C11 C6 120.3(3) . . ? C10 C11 H11 119.8 . . ? C6 C11 H11 119.8 . . ? C13 C12 C17 121.7(3) . . ? C13 C12 S1 117.8(2) . . ? C17 C12 S1 120.5(2) . . ? C14 C13 C12 119.5(3) . . ? C14 C13 H13 120.2 . . ? C12 C13 H13 120.2 . . ? C13 C14 C15 118.2(2) . . ? C13 C14 H14 120.9 . . ? C15 C14 H14 120.9 . . ? C16 C15 C14 122.8(3) . . ? C16 C15 N2 119.2(2) . . ? C14 C15 N2 118.0(2) . . ? C15 C16 C17 119.0(3) . . ? C15 C16 H16 120.5 . . ? C17 C16 H16 120.5 . . ? C12 C17 C16 118.8(3) . . ? C12 C17 H17 120.6 . . ? C16 C17 H17 120.6 . . ? 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 O1 H1 O3 0.84 2.01 2.819(3) 160.9 2_745 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.755 _refine_diff_density_min -0.706 _refine_diff_density_rms 0.115