# Electronic Supplementary Material (ESI) for Green Chemistry # 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_syn _database_code_depnum_ccdc_archive 'CCDC 853215' #TrackingRef '8086_web_deposit_cif_file_0_JyotirmayeeDash_1320827880.aldol.jd.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H10 N2 O5 S' _chemical_formula_sum 'C11 H10 N2 O5 S' _chemical_formula_weight 282.27 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c _symmetry_space_group_name_Hall '-P 2ybc' 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 10.7880(5) _cell_length_b 16.5308(8) _cell_length_c 7.1104(3) _cell_angle_alpha 90.00 _cell_angle_beta 106.8610(10) _cell_angle_gamma 90.00 _cell_volume 1213.52(10) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8359 _cell_measurement_theta_min 2.33 _cell_measurement_theta_max 35.60 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.534 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 584 _exptl_absorpt_coefficient_mu 0.285 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.940 _exptl_absorpt_correction_T_max 0.955 _exptl_absorpt_process_details 'Sadabs, Bruker 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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 12149 _diffrn_reflns_av_R_equivalents 0.0220 _diffrn_reflns_av_sigmaI/netI 0.0159 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.97 _diffrn_reflns_theta_max 27.00 _reflns_number_total 2639 _reflns_number_gt 2392 _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, 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^)+(0.0362P)^2^+0.5458P] 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 2639 _refine_ls_number_parameters 174 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0328 _refine_ls_R_factor_gt 0.0290 _refine_ls_wR_factor_ref 0.0787 _refine_ls_wR_factor_gt 0.0754 _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_restrained_S_all 1.069 _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 S1 S 0.20438(3) 0.50968(2) 0.44557(5) 0.02975(11) Uani 1 1 d . . . N1 N 0.36050(11) 0.38627(6) 0.50689(16) 0.0219(2) Uani 1 1 d . . . N2 N -0.04252(11) 0.78750(7) 0.85843(17) 0.0287(3) Uani 1 1 d . . . O1 O 0.27448(10) 0.42248(6) 0.18310(14) 0.0304(2) Uani 1 1 d . . . O2 O 0.43044(9) 0.37382(6) 0.83909(13) 0.0265(2) Uani 1 1 d . . . O3 O 0.43725(8) 0.57051(5) 0.78758(13) 0.0219(2) Uani 1 1 d . . . H10 H 0.4911 0.5889 0.8844 0.033 Uiso 1 1 calc R . . O4 O -0.01942(11) 0.85703(7) 0.8192(2) 0.0432(3) Uani 1 1 d . . . O5 O -0.14044(10) 0.76803(7) 0.90188(19) 0.0427(3) Uani 1 1 d . . . C1 C 0.28502(12) 0.43322(8) 0.35490(19) 0.0233(3) Uani 1 1 d . . . C2 C 0.36240(12) 0.40718(7) 0.69359(18) 0.0199(2) Uani 1 1 d . . . C3 C 0.26731(12) 0.47418(7) 0.69717(18) 0.0208(2) Uani 1 1 d . . . H4 H 0.1955 0.4509 0.7377 0.025 Uiso 1 1 calc R . . C4 C 0.32978(11) 0.54109(7) 0.84268(18) 0.0184(2) Uani 1 1 d . . . H5 H 0.3613 0.5173 0.9742 0.022 Uiso 1 1 calc R . . C5 C 0.23192(11) 0.60676(7) 0.84719(17) 0.0181(2) Uani 1 1 d . . . C6 C 0.11601(12) 0.58648(8) 0.88639(19) 0.0235(3) Uani 1 1 d . . . H9 H 0.0998 0.5329 0.9110 0.028 Uiso 1 1 calc R . . C7 C 0.02522(12) 0.64527(8) 0.8890(2) 0.0253(3) Uani 1 1 d . . . H8 H -0.0524 0.6317 0.9134 0.030 Uiso 1 1 calc R . . C8 C 0.05268(12) 0.72448(8) 0.85452(18) 0.0224(3) Uani 1 1 d . . . C9 C 0.16746(12) 0.74730(8) 0.81960(18) 0.0228(3) Uani 1 1 d . . . H7 H 0.1844 0.8013 0.7997 0.027 Uiso 1 1 calc R . . C10 C 0.25663(12) 0.68724(7) 0.81520(18) 0.0203(2) Uani 1 1 d . . . H10A H 0.3340 0.7011 0.7905 0.024 Uiso 1 1 calc R . . C11 C 0.43155(16) 0.31630(9) 0.4679(2) 0.0334(3) Uani 1 1 d . . . H11A H 0.5221 0.3292 0.5001 0.050 Uiso 1 1 calc R . . H11B H 0.3999 0.3022 0.3314 0.050 Uiso 1 1 calc R . . H11C H 0.4194 0.2715 0.5466 0.050 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 0.02952(19) 0.02513(18) 0.02676(18) -0.00312(12) -0.00423(14) 0.00652(13) N1 0.0259(5) 0.0170(5) 0.0249(5) 0.0003(4) 0.0106(4) -0.0003(4) N2 0.0219(5) 0.0307(6) 0.0310(6) -0.0064(5) 0.0037(5) 0.0067(5) O1 0.0335(5) 0.0347(5) 0.0230(5) -0.0004(4) 0.0081(4) -0.0075(4) O2 0.0333(5) 0.0186(4) 0.0257(5) 0.0016(4) 0.0054(4) 0.0022(4) O3 0.0158(4) 0.0220(4) 0.0279(5) -0.0022(4) 0.0064(3) -0.0025(3) O4 0.0360(6) 0.0246(5) 0.0697(8) -0.0023(5) 0.0166(6) 0.0097(4) O5 0.0265(5) 0.0451(7) 0.0606(7) -0.0028(6) 0.0194(5) 0.0093(5) C1 0.0211(6) 0.0212(6) 0.0266(6) 0.0003(5) 0.0052(5) -0.0069(5) C2 0.0215(6) 0.0137(5) 0.0254(6) -0.0003(5) 0.0080(5) -0.0037(4) C3 0.0196(6) 0.0172(6) 0.0250(6) -0.0014(5) 0.0055(5) -0.0017(5) C4 0.0173(5) 0.0167(6) 0.0210(6) -0.0001(4) 0.0051(4) -0.0008(4) C5 0.0180(6) 0.0186(6) 0.0167(5) -0.0015(4) 0.0034(4) 0.0001(4) C6 0.0218(6) 0.0206(6) 0.0294(6) -0.0004(5) 0.0096(5) -0.0021(5) C7 0.0183(6) 0.0290(7) 0.0290(7) -0.0031(5) 0.0077(5) -0.0012(5) C8 0.0189(6) 0.0244(6) 0.0220(6) -0.0044(5) 0.0030(5) 0.0048(5) C9 0.0236(6) 0.0184(6) 0.0249(6) -0.0015(5) 0.0046(5) 0.0010(5) C10 0.0187(5) 0.0201(6) 0.0220(6) -0.0010(5) 0.0057(5) -0.0007(5) C11 0.0466(9) 0.0253(7) 0.0347(7) 0.0012(6) 0.0217(7) 0.0098(6) _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 C1 1.7594(14) . ? S1 C3 1.8170(13) . ? N1 C2 1.3662(16) . ? N1 C1 1.3867(17) . ? N1 C11 1.4579(17) . ? N2 O4 1.2252(17) . ? N2 O5 1.2266(16) . ? N2 C8 1.4687(16) . ? O1 C1 1.2067(16) . ? O2 C2 1.2135(16) . ? O3 C4 1.4134(14) . ? O3 H10 0.8200 . ? C2 C3 1.5148(17) . ? C3 C4 1.5308(16) . ? C3 H4 0.9800 . ? C4 C5 1.5212(16) . ? C4 H5 0.9800 . ? C5 C10 1.3885(17) . ? C5 C6 1.3986(17) . ? C6 C7 1.3837(18) . ? C6 H9 0.9300 . ? C7 C8 1.3800(19) . ? C7 H8 0.9300 . ? C8 C9 1.3841(18) . ? C9 C10 1.3890(17) . ? C9 H7 0.9300 . ? C10 H10A 0.9300 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? 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 C1 S1 C3 92.61(6) . . ? C2 N1 C1 117.10(11) . . ? C2 N1 C11 121.66(11) . . ? C1 N1 C11 121.21(11) . . ? O4 N2 O5 123.39(12) . . ? O4 N2 C8 118.14(12) . . ? O5 N2 C8 118.47(12) . . ? C4 O3 H10 109.5 . . ? O1 C1 N1 124.63(13) . . ? O1 C1 S1 124.41(11) . . ? N1 C1 S1 110.95(9) . . ? O2 C2 N1 123.25(12) . . ? O2 C2 C3 124.26(11) . . ? N1 C2 C3 112.46(11) . . ? C2 C3 C4 111.85(10) . . ? C2 C3 S1 106.32(9) . . ? C4 C3 S1 113.42(8) . . ? C2 C3 H4 108.4 . . ? C4 C3 H4 108.4 . . ? S1 C3 H4 108.4 . . ? O3 C4 C5 112.98(10) . . ? O3 C4 C3 107.28(10) . . ? C5 C4 C3 110.96(10) . . ? O3 C4 H5 108.5 . . ? C5 C4 H5 108.5 . . ? C3 C4 H5 108.5 . . ? C10 C5 C6 119.19(11) . . ? C10 C5 C4 120.86(11) . . ? C6 C5 C4 119.95(11) . . ? C7 C6 C5 120.76(12) . . ? C7 C6 H9 119.6 . . ? C5 C6 H9 119.6 . . ? C8 C7 C6 118.35(12) . . ? C8 C7 H8 120.8 . . ? C6 C7 H8 120.8 . . ? C7 C8 C9 122.66(12) . . ? C7 C8 N2 118.84(12) . . ? C9 C8 N2 118.49(12) . . ? C8 C9 C10 118.09(12) . . ? C8 C9 H7 121.0 . . ? C10 C9 H7 121.0 . . ? C5 C10 C9 120.93(12) . . ? C5 C10 H10A 119.5 . . ? C9 C10 H10A 119.5 . . ? N1 C11 H11A 109.5 . . ? N1 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? N1 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.306 _refine_diff_density_min -0.230 _refine_diff_density_rms 0.044 data_jd_sp_396 _database_code_depnum_ccdc_archive 'CCDC 860928' #TrackingRef 'web_deposit_cif_file_0_JyotirmayeeDash_1325566498.JD_SP_396.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C8 H6 Br2 N2 O3 S2, O' _chemical_formula_sum 'C8 H6 Br2 N2 O4 S2' _chemical_formula_weight 418.09 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 _symmetry_space_group_name_Hall '-P 2ybc' 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 20.804(2) _cell_length_b 11.9934(14) _cell_length_c 10.9684(11) _cell_angle_alpha 90.00 _cell_angle_beta 102.666(2) _cell_angle_gamma 90.00 _cell_volume 2670.1(5) _cell_formula_units_Z 8 _cell_measurement_temperature 100 _cell_measurement_reflns_used 7308 _cell_measurement_theta_min 2.55 _cell_measurement_theta_max 25.04 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.080 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1616 _exptl_absorpt_coefficient_mu 6.381 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.221 _exptl_absorpt_correction_T_max 0.384 _exptl_absorpt_process_details 'SADABS; BRUKER, 2008' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100 _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 19654 _diffrn_reflns_av_R_equivalents 0.0495 _diffrn_reflns_av_sigmaI/netI 0.0427 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.00 _diffrn_reflns_theta_max 25.06 _reflns_number_total 4717 _reflns_number_gt 4166 _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^)+(0.0375P)^2^+170.2517P] 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 4717 _refine_ls_number_parameters 257 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0913 _refine_ls_R_factor_gt 0.0840 _refine_ls_wR_factor_ref 0.2132 _refine_ls_wR_factor_gt 0.2092 _refine_ls_goodness_of_fit_ref 1.149 _refine_ls_restrained_S_all 1.149 _refine_ls_shift/su_max 0.006 _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 O1 O 0.5498(4) 0.8311(7) -0.0186(9) 0.0115(18) Uani 1 1 d . . . H1 H 0.5139 0.8142 -0.0623 0.017 Uiso 1 1 calc R . . O2 O 0.6758(4) 0.8775(7) -0.1627(8) 0.0106(6) Uani 1 1 d . . . O3 O 0.6791(4) 1.0749(8) 0.1927(9) 0.015(2) Uani 1 1 d . . . O4 O 0.9477(4) 0.8246(7) 0.9261(9) 0.0138(19) Uani 1 1 d . . . H4 H 0.9298 0.8793 0.9488 0.021 Uiso 1 1 calc R . . O5 O 0.8119(5) 0.8625(8) 0.6823(9) 0.019(2) Uani 1 1 d . . . O6 O 0.8292(4) 1.0774(7) 1.0306(9) 0.015(2) Uani 1 1 d . . . O7 O 0.0658(5) 0.7310(8) 0.3875(9) 0.020(2) Uani 1 1 d . . . O8 O 0.5690(5) 0.2276(8) 0.1567(10) 0.021(2) Uani 1 1 d . . . S1 S 0.52437(15) 0.6582(3) 0.1516(3) 0.0090(6) Uani 1 1 d . . . S2 S 0.67406(15) 0.8530(3) 0.1871(3) 0.0106(6) Uani 1 1 d . . . S3 S 0.97452(15) 0.6598(3) 1.1243(3) 0.0108(6) Uani 1 1 d . . . S4 S 0.83063(15) 0.8583(3) 1.0401(3) 0.0115(6) Uani 1 1 d . . . Br1 Br 0.49121(6) 0.45179(10) 0.30049(12) 0.0116(3) Uani 1 1 d . . . Br2 Br 0.66123(7) 0.48253(11) -0.02968(13) 0.0161(3) Uani 1 1 d . . . Br3 Br 1.00952(6) 0.45697(10) 1.30726(12) 0.0140(3) Uani 1 1 d . . . Br4 Br 0.83365(7) 0.47570(11) 0.84354(13) 0.0206(4) Uani 1 1 d . . . C1 C 0.5360(6) 0.5197(10) 0.1904(12) 0.0090(6) Uani 1 1 d . . . C2 C 0.6021(6) 0.5391(11) 0.0616(12) 0.0100(18) Uani 1 1 d . . . C3 C 0.5795(6) 0.6446(11) 0.0566(12) 0.0100(18) Uani 1 1 d . . . C4 C 0.5948(6) 0.7423(10) -0.0181(12) 0.0091(18) Uani 1 1 d . . . H4A H 0.5919 0.7180 -0.1045 0.011 Uiso 1 1 calc R . . C5 C 0.6637(6) 0.7942(10) 0.0321(12) 0.0091(18) Uani 1 1 d . . . H5 H 0.6977 0.7376 0.0321 0.011 Uiso 1 1 calc R . . C6 C 0.6725(6) 0.8889(11) -0.0543(12) 0.0106(6) Uani 1 1 d . . . C7 C 0.6747(6) 0.9921(11) 0.1270(12) 0.0106(6) Uani 1 1 d . . . C8 C 0.6710(6) 1.0985(12) -0.0615(14) 0.019(3) Uani 1 1 d . . . H8A H 0.6332 1.1404 -0.0509 0.028 Uiso 1 1 calc R . . H8B H 0.6684 1.0862 -0.1489 0.028 Uiso 1 1 calc R . . H8C H 0.7104 1.1394 -0.0266 0.028 Uiso 1 1 calc R . . C9 C 0.9627(6) 0.5229(10) 1.1596(11) 0.0089(16) Uani 1 1 d . . . C10 C 0.8963(6) 0.5354(10) 0.9773(12) 0.011(3) Uani 1 1 d . . . C11 C 0.9181(6) 0.6433(11) 0.9843(12) 0.011(3) Uani 1 1 d . . . C12 C 0.9012(6) 0.7372(11) 0.8948(13) 0.0133(16) Uani 1 1 d . . . H12 H 0.9018 0.7103 0.8107 0.016 Uiso 1 1 calc R . . C13 C 0.8329(6) 0.7892(11) 0.8933(12) 0.0133(16) Uani 1 1 d . . . H13 H 0.7986 0.7318 0.8749 0.016 Uiso 1 1 calc R . . C14 C 0.8196(6) 0.8804(11) 0.7927(12) 0.0133(16) Uani 1 1 d . . . C15 C 0.8266(6) 0.9920(11) 0.9695(12) 0.0115(6) Uani 1 1 d . . . C16 C 0.8138(6) 1.0872(11) 0.7657(14) 0.0154(19) Uani 1 1 d . . . H16A H 0.7797 1.1338 0.7842 0.023 Uiso 1 1 calc R . . H16B H 0.8027 1.0660 0.6793 0.023 Uiso 1 1 calc R . . H16C H 0.8548 1.1273 0.7825 0.023 Uiso 1 1 calc R . . N1 N 0.5769(5) 0.4655(9) 0.1368(9) 0.009(2) Uani 1 1 d . . . N2 N 0.6724(5) 0.9910(9) 0.0024(10) 0.0106(6) Uani 1 1 d . . . N3 N 0.9223(5) 0.4663(8) 1.0758(10) 0.0089(16) Uani 1 1 d . . . N4 N 0.8205(5) 0.9866(9) 0.8443(11) 0.0154(19) 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 O1 0.009(4) 0.009(4) 0.016(5) -0.002(4) 0.001(4) 0.002(4) O2 0.0095(13) 0.0111(13) 0.0112(13) 0.0006(10) 0.0021(10) -0.0005(10) O3 0.011(4) 0.021(5) 0.014(5) -0.001(4) 0.004(4) -0.001(4) O4 0.013(5) 0.006(4) 0.021(5) 0.002(4) 0.002(4) -0.002(4) O5 0.030(6) 0.018(5) 0.011(5) 0.002(4) 0.007(4) 0.007(4) O6 0.012(5) 0.009(4) 0.023(5) -0.004(4) -0.001(4) -0.004(4) O7 0.015(5) 0.017(5) 0.026(6) -0.001(4) 0.003(4) -0.002(4) O8 0.016(5) 0.013(5) 0.031(6) -0.002(4) -0.003(4) -0.002(4) S1 0.0094(14) 0.0071(14) 0.0114(15) 0.0010(11) 0.0041(11) -0.0001(11) S2 0.0095(13) 0.0111(13) 0.0112(13) 0.0006(10) 0.0021(10) -0.0005(10) S3 0.0116(15) 0.0088(15) 0.0103(15) -0.0007(12) -0.0010(12) 0.0006(12) S4 0.0102(14) 0.0098(15) 0.0136(15) -0.0006(12) 0.0008(12) -0.0001(12) Br1 0.0133(6) 0.0082(6) 0.0154(6) 0.0012(5) 0.0077(5) -0.0024(5) Br2 0.0203(7) 0.0132(7) 0.0189(7) 0.0006(5) 0.0132(5) 0.0048(5) Br3 0.0162(7) 0.0098(6) 0.0127(6) 0.0012(5) -0.0037(5) 0.0033(5) Br4 0.0236(7) 0.0122(7) 0.0191(7) -0.0008(5) -0.0101(6) -0.0040(5) C1 0.0094(14) 0.0071(14) 0.0114(15) 0.0010(11) 0.0041(11) -0.0001(11) C2 0.009(4) 0.012(4) 0.011(4) -0.002(3) 0.007(3) -0.004(3) C3 0.009(4) 0.012(4) 0.011(4) -0.002(3) 0.007(3) -0.004(3) C4 0.003(4) 0.012(4) 0.012(4) 0.003(4) 0.000(3) 0.000(3) C5 0.003(4) 0.012(4) 0.012(4) 0.003(4) 0.000(3) 0.000(3) C6 0.0095(13) 0.0111(13) 0.0112(13) 0.0006(10) 0.0021(10) -0.0005(10) C7 0.0095(13) 0.0111(13) 0.0112(13) 0.0006(10) 0.0021(10) -0.0005(10) C8 0.004(6) 0.029(8) 0.023(8) -0.007(6) 0.003(5) -0.002(6) C9 0.010(4) 0.006(4) 0.011(4) -0.001(3) 0.002(3) 0.003(3) C10 0.013(6) 0.007(6) 0.009(6) 0.002(5) -0.006(5) 0.001(5) C11 0.009(6) 0.017(7) 0.008(6) 0.000(5) 0.002(5) -0.001(5) C12 0.010(4) 0.012(4) 0.017(4) -0.004(3) 0.001(3) -0.003(3) C13 0.010(4) 0.012(4) 0.017(4) -0.004(3) 0.001(3) -0.003(3) C14 0.010(4) 0.012(4) 0.017(4) -0.004(3) 0.001(3) -0.003(3) C15 0.0102(14) 0.0098(15) 0.0136(15) -0.0006(12) 0.0008(12) -0.0001(12) C16 0.012(4) 0.007(4) 0.027(5) 0.008(4) 0.005(4) 0.006(3) N1 0.014(5) 0.008(5) 0.004(5) -0.001(4) -0.001(4) -0.002(4) N2 0.0095(13) 0.0111(13) 0.0112(13) 0.0006(10) 0.0021(10) -0.0005(10) N3 0.010(4) 0.006(4) 0.011(4) -0.001(3) 0.002(3) 0.003(3) N4 0.012(4) 0.007(4) 0.027(5) 0.008(4) 0.005(4) 0.006(3) _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 O1 C4 1.418(15) . ? O1 H1 0.8200 . ? O2 C6 1.213(16) . ? O3 C7 1.219(16) . ? O4 C12 1.418(15) . ? O4 H4 0.8200 . ? O5 C14 1.205(17) . ? O6 C15 1.219(16) . ? S1 C1 1.718(12) . ? S1 C3 1.718(12) . ? S2 C7 1.795(13) . ? S2 C5 1.809(13) . ? S3 C9 1.717(12) . ? S3 C11 1.728(13) . ? S4 C15 1.775(13) . ? S4 C13 1.820(13) . ? Br1 C1 1.867(12) . ? Br2 C2 1.875(12) . ? Br3 C9 1.873(12) . ? Br4 C10 1.877(12) . ? C1 N1 1.308(16) . ? C2 C3 1.347(18) . ? C2 N1 1.387(16) . ? C3 C4 1.504(17) . ? C4 C5 1.549(16) . ? C4 H4A 0.9800 . ? C5 C6 1.517(17) . ? C5 H5 0.9800 . ? C6 N2 1.373(17) . ? C7 N2 1.357(17) . ? C8 N2 1.465(18) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 N3 1.293(16) . ? C10 C11 1.367(18) . ? C10 N3 1.375(16) . ? C11 C12 1.485(18) . ? C12 C13 1.549(18) . ? C12 H12 0.9800 . ? C13 C14 1.535(19) . ? C13 H13 0.9800 . ? C14 N4 1.392(17) . ? C15 N4 1.352(18) . ? C16 N4 1.471(16) . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? 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 C4 O1 H1 109.5 . . ? C12 O4 H4 109.5 . . ? C1 S1 C3 89.0(6) . . ? C7 S2 C5 91.5(6) . . ? C9 S3 C11 89.2(6) . . ? C15 S4 C13 91.9(6) . . ? N1 C1 S1 116.1(9) . . ? N1 C1 Br1 122.7(9) . . ? S1 C1 Br1 121.3(7) . . ? C3 C2 N1 116.6(11) . . ? C3 C2 Br2 125.6(10) . . ? N1 C2 Br2 117.7(9) . . ? C2 C3 C4 129.8(11) . . ? C2 C3 S1 109.8(9) . . ? C4 C3 S1 120.4(9) . . ? O1 C4 C3 111.6(10) . . ? O1 C4 C5 105.0(10) . . ? C3 C4 C5 114.1(10) . . ? O1 C4 H4A 108.6 . . ? C3 C4 H4A 108.6 . . ? C5 C4 H4A 108.6 . . ? C6 C5 C4 107.8(10) . . ? C6 C5 S2 106.8(9) . . ? C4 C5 S2 113.6(9) . . ? C6 C5 H5 109.5 . . ? C4 C5 H5 109.5 . . ? S2 C5 H5 109.5 . . ? O2 C6 N2 123.4(12) . . ? O2 C6 C5 124.6(12) . . ? N2 C6 C5 111.9(11) . . ? O3 C7 N2 125.8(12) . . ? O3 C7 S2 123.1(10) . . ? N2 C7 S2 111.1(9) . . ? N2 C8 H8A 109.5 . . ? N2 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N2 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N3 C9 S3 116.4(9) . . ? N3 C9 Br3 121.8(9) . . ? S3 C9 Br3 121.7(7) . . ? C11 C10 N3 117.2(11) . . ? C11 C10 Br4 124.7(9) . . ? N3 C10 Br4 118.1(9) . . ? C10 C11 C12 130.8(12) . . ? C10 C11 S3 108.1(9) . . ? C12 C11 S3 121.1(10) . . ? O4 C12 C11 110.6(10) . . ? O4 C12 C13 106.3(10) . . ? C11 C12 C13 113.3(11) . . ? O4 C12 H12 108.8 . . ? C11 C12 H12 108.8 . . ? C13 C12 H12 108.8 . . ? C14 C13 C12 108.4(11) . . ? C14 C13 S4 106.0(9) . . ? C12 C13 S4 112.1(9) . . ? C14 C13 H13 110.1 . . ? C12 C13 H13 110.1 . . ? S4 C13 H13 110.1 . . ? O5 C14 N4 124.0(13) . . ? O5 C14 C13 123.9(12) . . ? N4 C14 C13 112.0(11) . . ? O6 C15 N4 125.6(12) . . ? O6 C15 S4 121.8(10) . . ? N4 C15 S4 112.6(9) . . ? N4 C16 H16A 109.5 . . ? N4 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? N4 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C1 N1 C2 108.6(10) . . ? C7 N2 C6 117.5(11) . . ? C7 N2 C8 117.8(11) . . ? C6 N2 C8 124.7(11) . . ? C9 N3 C10 109.0(11) . . ? C15 N4 C14 116.5(11) . . ? C15 N4 C16 122.1(11) . . ? C14 N4 C16 121.4(12) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.06 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 2.625 _refine_diff_density_min -1.579 _refine_diff_density_rms 0.311