# 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, 2009 data_global _journal_coden_Cambridge 440 loop_ _publ_author_name 'Darko Dolenc' 'Barbara Modec' _publ_contact_author_name 'Darko Dolenc' _publ_contact_author_email darko.dolenc@fkkt.uni-lj.si _publ_section_title ; EDA Complexes of N-halosaccharins with N- and O-donor ligands ; #=============================================================== # EDA Complexes of N-halosaccharins with N- and # O-donor ligands. # # by # # Darko Dolenc and Barbara Modec # #===================================================================== data_NISac.H2O _database_code_depnum_ccdc_archive 'CCDC 746490' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C7 H6 I N O4 S' _chemical_formula_weight 327.09 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' 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/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 8.4574(2) _cell_length_b 9.0194(2) _cell_length_c 12.9095(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.2461(14) _cell_angle_gamma 90.00 _cell_volume 984.74(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.206 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 624 _exptl_absorpt_coefficient_mu 3.451 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7241 _exptl_absorpt_correction_T_max 0.8197 _exptl_absorpt_process_details ; HKL SCALEPACK (Otwinowski & Minor, 1997) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'Nonius Kappa CCD diffractometer' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4319 _diffrn_reflns_av_R_equivalents 0.0138 _diffrn_reflns_av_sigmaI/netI 0.0213 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.89 _diffrn_reflns_theta_max 27.45 _reflns_number_total 2239 _reflns_number_gt 2025 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_cell_refinement 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0203P)^2^+0.9634P] 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_number_reflns 2239 _refine_ls_number_parameters 135 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0222 _refine_ls_R_factor_gt 0.0187 _refine_ls_wR_factor_ref 0.0466 _refine_ls_wR_factor_gt 0.0451 _refine_ls_goodness_of_fit_ref 1.086 _refine_ls_restrained_S_all 1.086 _refine_ls_shift/su_max 0.003 _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 I1 I 0.495878(16) 0.666711(16) 0.793880(11) 0.01551(6) Uani 1 1 d . . . S1 S 0.23798(6) 0.48423(6) 0.93483(4) 0.01439(12) Uani 1 1 d . . . O1S O 0.2891(2) 0.57112(19) 1.02149(13) 0.0213(4) Uani 1 1 d . . . O1 O 0.6370(3) 0.8897(2) 0.73956(15) 0.0223(4) Uani 1 1 d . . . H1O H 0.714(4) 0.882(4) 0.731(3) 0.035(11) Uiso 1 1 d . . . H2O H 0.592(5) 0.926(5) 0.678(3) 0.061(12) Uiso 1 1 d . . . O2S O 0.09204(19) 0.52847(19) 0.88682(13) 0.0216(4) Uani 1 1 d . . . O7 O 0.5480(2) 0.3073(2) 0.77141(14) 0.0223(4) Uani 1 1 d . . . N1 N 0.3799(2) 0.4756(2) 0.84616(15) 0.0169(4) Uani 1 1 d . . . C1 C 0.2418(3) 0.2926(3) 0.95866(17) 0.0152(4) Uani 1 1 d . . . C2 C 0.1518(3) 0.2129(3) 1.02878(18) 0.0191(5) Uani 1 1 d . . . H2 H 0.0783 0.2588 1.0714 0.023 Uiso 1 1 calc R . . C3 C 0.1774(3) 0.0605(3) 1.03205(19) 0.0207(5) Uani 1 1 d . . . H3 H 0.1204 0.0031 1.0787 0.025 Uiso 1 1 calc R . . C4 C 0.2861(3) -0.0080(3) 0.96712(19) 0.0218(5) Uani 1 1 d . . . H4 H 0.2992 -0.1103 0.9703 0.026 Uiso 1 1 calc R . . C5 C 0.3755(3) 0.0741(3) 0.89762(19) 0.0198(5) Uani 1 1 d . . . H5 H 0.4484 0.0283 0.8544 0.024 Uiso 1 1 calc R . . C6 C 0.3529(3) 0.2265(3) 0.89457(18) 0.0156(5) Uani 1 1 d . . . C7 C 0.4396(3) 0.3346(2) 0.82976(19) 0.0162(5) 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 0.01461(9) 0.01682(9) 0.01513(9) 0.00092(5) 0.00143(6) 0.00061(5) S1 0.0141(3) 0.0149(3) 0.0142(3) -0.0013(2) 0.0020(2) 0.0013(2) O1S 0.0264(9) 0.0204(9) 0.0172(9) -0.0063(7) 0.0012(7) -0.0015(7) O1 0.0173(10) 0.0247(10) 0.0251(10) 0.0056(8) 0.0047(8) -0.0002(8) O2S 0.0167(8) 0.0214(9) 0.0267(9) 0.0004(7) -0.0004(7) 0.0053(7) O7 0.0199(9) 0.0250(9) 0.0221(9) -0.0062(7) 0.0090(7) -0.0006(7) N1 0.0160(9) 0.0157(9) 0.0192(10) 0.0006(8) 0.0062(7) -0.0011(8) C1 0.0144(11) 0.0163(10) 0.0149(11) -0.0022(9) -0.0003(8) 0.0014(9) C2 0.0180(12) 0.0228(12) 0.0165(12) 0.0002(10) 0.0032(9) 0.0010(10) C3 0.0208(12) 0.0214(12) 0.0200(12) 0.0044(10) 0.0015(9) -0.0042(10) C4 0.0239(12) 0.0146(11) 0.0270(13) 0.0009(10) -0.0023(10) 0.0001(10) C5 0.0166(11) 0.0189(12) 0.0239(13) -0.0048(10) 0.0014(9) 0.0029(9) C6 0.0125(10) 0.0201(12) 0.0144(11) -0.0025(9) 0.0000(8) 0.0009(9) C7 0.0139(11) 0.0197(12) 0.0150(11) -0.0037(9) -0.0006(8) -0.0010(9) _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 N1 2.0961(19) . ? I1 O1 2.4431(19) . ? S1 O1S 1.4312(17) . ? S1 O2S 1.4353(17) . ? S1 N1 1.664(2) . ? S1 C1 1.756(2) . ? O1 H1O 0.67(4) . ? O1 H2O 0.94(4) . ? O7 C7 1.215(3) . ? N1 C7 1.386(3) . ? C1 C2 1.386(3) . ? C1 C6 1.389(3) . ? C2 C3 1.392(4) . ? C2 H2 0.9300 . ? C3 C4 1.392(4) . ? C3 H3 0.9300 . ? C4 C5 1.390(3) . ? C4 H4 0.9300 . ? C5 C6 1.388(4) . ? C5 H5 0.9300 . ? C6 C7 1.481(3) . ? 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 N1 I1 O1 177.68(7) . . ? O1S S1 O2S 116.20(10) . . ? O1S S1 N1 110.31(10) . . ? O2S S1 N1 109.71(10) . . ? O1S S1 C1 113.38(11) . . ? O2S S1 C1 111.36(11) . . ? N1 S1 C1 93.56(10) . . ? I1 O1 H1O 116(3) . . ? I1 O1 H2O 109(3) . . ? H1O O1 H2O 107(4) . . ? C7 N1 S1 114.35(16) . . ? C7 N1 I1 122.30(15) . . ? S1 N1 I1 121.55(11) . . ? C2 C1 C6 122.7(2) . . ? C2 C1 S1 127.99(19) . . ? C6 C1 S1 109.26(17) . . ? C1 C2 C3 116.5(2) . . ? C1 C2 H2 121.7 . . ? C3 C2 H2 121.7 . . ? C4 C3 C2 121.5(2) . . ? C4 C3 H3 119.2 . . ? C2 C3 H3 119.2 . . ? C5 C4 C3 121.0(2) . . ? C5 C4 H4 119.5 . . ? C3 C4 H4 119.5 . . ? C6 C5 C4 118.1(2) . . ? C6 C5 H5 121.0 . . ? C4 C5 H5 121.0 . . ? C5 C6 C1 120.1(2) . . ? C5 C6 C7 126.8(2) . . ? C1 C6 C7 113.1(2) . . ? O7 C7 N1 123.9(2) . . ? O7 C7 C6 126.5(2) . . ? N1 C7 C6 109.65(19) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.45 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.379 _refine_diff_density_min -0.595 _refine_diff_density_rms 0.102 #===END data_NISac.THF _database_code_depnum_ccdc_archive 'CCDC 746491' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H12 I N O4 S' _chemical_formula_weight 381.18 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' I I -0.4742 1.8119 '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 orthorhombic _symmetry_space_group_name_H-M 'P m n b' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y+1/2, z+1/2' 'x+1/2, -y, -z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, y-1/2, -z-1/2' '-x-1/2, y, z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.24280(10) _cell_length_b 9.14280(10) _cell_length_c 17.6493(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1330.09(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(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 0.12 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.904 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 744 _exptl_absorpt_coefficient_mu 2.570 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7479 _exptl_absorpt_correction_T_max 0.8823 _exptl_absorpt_process_details ; HKL SCALEPACK (Otwinowski & Minor, 1997) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'Nonius Kappa CCD diffractometer' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2880 _diffrn_reflns_av_R_equivalents 0.0093 _diffrn_reflns_av_sigmaI/netI 0.0193 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 4.62 _diffrn_reflns_theta_max 27.47 _reflns_number_total 1605 _reflns_number_gt 1534 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_cell_refinement 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0204P)^2^+1.6216P] 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 1605 _refine_ls_number_parameters 100 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0226 _refine_ls_R_factor_gt 0.0212 _refine_ls_wR_factor_ref 0.0528 _refine_ls_wR_factor_gt 0.0521 _refine_ls_goodness_of_fit_ref 1.129 _refine_ls_restrained_S_all 1.129 _refine_ls_shift/su_max 0.003 _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 I1 I 0.2500 0.32547(2) 0.551023(10) 0.02159(8) Uani 1 2 d S . . S1 S 0.2500 -0.02890(8) 0.54098(4) 0.01706(15) Uani 1 2 d S . . O1S O 0.10209(19) -0.04487(17) 0.58272(8) 0.0248(3) Uani 1 1 d . . . O2 O 0.2500 0.5611(2) 0.62421(12) 0.0263(5) Uani 1 2 d S . . O7 O 0.2500 0.2189(2) 0.37179(12) 0.0235(5) Uani 1 2 d S . . C1 C 0.2500 -0.1340(3) 0.45758(15) 0.0177(6) Uani 1 2 d S . . C2 C 0.2500 -0.2848(4) 0.45238(17) 0.0226(6) Uani 1 2 d S . . H2 H 0.2500 -0.3438 0.4953 0.027 Uiso 1 2 calc SR . . C3 C 0.2500 -0.3441(3) 0.3796(2) 0.0258(7) Uani 1 2 d S . . H3 H 0.2500 -0.4451 0.3736 0.031 Uiso 1 2 calc SR . . C4 C 0.2500 -0.2549(3) 0.31621(18) 0.0254(6) Uani 1 2 d S . . H4 H 0.2500 -0.2971 0.2683 0.031 Uiso 1 2 calc SR . . C5 C 0.2500 -0.1032(3) 0.32288(16) 0.0223(6) Uani 1 2 d S . . H5 H 0.2500 -0.0440 0.2800 0.027 Uiso 1 2 calc SR . . C6 C 0.2500 -0.0425(3) 0.39477(16) 0.0175(5) Uani 1 2 d S . . C7 C 0.2500 0.1157(3) 0.41527(16) 0.0197(6) Uani 1 2 d S . . C21 C 0.1075(3) 0.5928(3) 0.66894(14) 0.0332(5) Uani 1 1 d . . . H21A H 0.0602 0.5030 0.6882 0.040 Uiso 1 1 calc R . . H21B H 0.0269 0.6429 0.6385 0.040 Uiso 1 1 calc R . . C22 C 0.1614(4) 0.6876(4) 0.73257(18) 0.0578(9) Uani 1 1 d . . . H22A H 0.1207 0.7863 0.7258 0.069 Uiso 1 1 calc R . . H22B H 0.1207 0.6499 0.7803 0.069 Uiso 1 1 calc R . . N1 N 0.2500 0.1281(3) 0.49328(14) 0.0207(5) Uani 1 2 d S . . 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 0.02947(13) 0.01643(12) 0.01888(12) -0.00165(6) 0.000 0.000 S1 0.0189(3) 0.0169(3) 0.0154(3) 0.0018(2) 0.000 0.000 O1S 0.0237(8) 0.0294(8) 0.0214(7) 0.0023(6) 0.0062(6) 0.0003(6) O2 0.0314(12) 0.0229(11) 0.0245(11) -0.0060(9) 0.000 0.000 O7 0.0327(12) 0.0171(10) 0.0208(10) 0.0050(8) 0.000 0.000 C1 0.0164(14) 0.0193(14) 0.0175(13) -0.0007(10) 0.000 0.000 C2 0.0237(15) 0.0198(15) 0.0243(15) 0.0013(11) 0.000 0.000 C3 0.0260(16) 0.0199(15) 0.0315(17) -0.0056(12) 0.000 0.000 C4 0.0277(16) 0.0252(15) 0.0234(14) -0.0071(12) 0.000 0.000 C5 0.0261(15) 0.0226(15) 0.0181(13) 0.0003(11) 0.000 0.000 C6 0.0150(13) 0.0187(14) 0.0190(13) -0.0011(11) 0.000 0.000 C7 0.0217(14) 0.0203(14) 0.0172(13) -0.0013(11) 0.000 0.000 C21 0.0256(12) 0.0298(12) 0.0441(14) -0.0073(10) 0.0005(10) 0.0018(10) C22 0.0382(17) 0.091(3) 0.0437(17) -0.0356(16) 0.0010(13) 0.0038(16) N1 0.0300(14) 0.0137(11) 0.0185(12) -0.0022(9) 0.000 0.000 _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 N1 2.073(2) . ? S1 O1S 1.4319(15) 7_655 ? S1 O1S 1.4319(15) . ? S1 N1 1.664(3) . ? S1 C1 1.758(3) . ? O2 C21 1.445(3) . ? O2 C21 1.445(3) 7_655 ? O7 C7 1.217(4) . ? C1 C2 1.382(4) . ? C1 C6 1.389(4) . ? C2 C3 1.394(4) . ? C2 H2 0.9300 . ? C3 C4 1.385(5) . ? C3 H3 0.9300 . ? C4 C5 1.391(5) . ? C4 H4 0.9300 . ? C5 C6 1.385(4) . ? C5 H5 0.9300 . ? C6 C7 1.490(4) . ? C7 N1 1.381(4) . ? C21 C22 1.486(4) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 C22 1.461(6) 7_655 ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? 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 O1S S1 O1S 116.74(13) 7_655 . ? O1S S1 N1 110.38(8) 7_655 . ? O1S S1 N1 110.38(8) . . ? O1S S1 C1 112.03(8) 7_655 . ? O1S S1 C1 112.03(8) . . ? N1 S1 C1 92.73(13) . . ? C21 O2 C21 108.8(2) . 7_655 ? C2 C1 C6 123.2(3) . . ? C2 C1 S1 126.9(2) . . ? C6 C1 S1 109.8(2) . . ? C1 C2 C3 116.7(3) . . ? C1 C2 H2 121.7 . . ? C3 C2 H2 121.7 . . ? C4 C3 C2 121.0(3) . . ? C4 C3 H3 119.5 . . ? C2 C3 H3 119.5 . . ? C3 C4 C5 121.2(3) . . ? C3 C4 H4 119.4 . . ? C5 C4 H4 119.4 . . ? C6 C5 C4 118.5(3) . . ? C6 C5 H5 120.7 . . ? C4 C5 H5 120.7 . . ? C5 C6 C1 119.3(3) . . ? C5 C6 C7 127.7(3) . . ? C1 C6 C7 113.0(2) . . ? O7 C7 N1 124.4(3) . . ? O7 C7 C6 126.8(3) . . ? N1 C7 C6 108.8(2) . . ? O2 C21 C22 106.6(2) . . ? O2 C21 H21A 110.4 . . ? C22 C21 H21A 110.4 . . ? O2 C21 H21B 110.4 . . ? C22 C21 H21B 110.4 . . ? H21A C21 H21B 108.6 . . ? C22 C22 C21 107.40(15) 7_655 . ? C22 C22 H22A 110.2 7_655 . ? C21 C22 H22A 110.2 . . ? C22 C22 H22B 110.2 7_655 . ? C21 C22 H22B 110.2 . . ? H22A C22 H22B 108.5 . . ? C7 N1 S1 115.69(19) . . ? C7 N1 I1 124.16(19) . . ? S1 N1 I1 120.15(13) . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.406 _refine_diff_density_min -0.519 _refine_diff_density_rms 0.084 #===END data_NISac.Py _database_code_depnum_ccdc_archive 'CCDC 746492' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H9 I N2 O3 S' _chemical_formula_weight 388.17 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' 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/a' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 12.6184(3) _cell_length_b 7.8019(2) _cell_length_c 14.8718(4) _cell_angle_alpha 90.00 _cell_angle_beta 113.6530(12) _cell_angle_gamma 90.00 _cell_volume 1341.10(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.923 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 752 _exptl_absorpt_coefficient_mu 2.548 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6570 _exptl_absorpt_correction_T_max 0.8832 _exptl_absorpt_process_details ; HKL SCALEPACK (Otwinowski & Minor, 1997) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Nonius Kappa CCD diffractometer' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5589 _diffrn_reflns_av_R_equivalents 0.0207 _diffrn_reflns_av_sigmaI/netI 0.0236 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.01 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3044 _reflns_number_gt 2829 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_cell_refinement 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.1200P)^2^+32.8590P] 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 3044 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0907 _refine_ls_R_factor_gt 0.0879 _refine_ls_wR_factor_ref 0.2702 _refine_ls_wR_factor_gt 0.2685 _refine_ls_goodness_of_fit_ref 1.120 _refine_ls_restrained_S_all 1.120 _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 I1 I 0.23612(7) 0.10215(10) 0.93133(6) 0.0401(3) Uani 1 1 d . . . S1 S 0.1464(3) 0.0270(5) 0.6918(2) 0.0434(7) Uani 1 1 d . . . O1S O 0.0863(10) -0.1129(16) 0.7085(9) 0.064(3) Uani 1 1 d . . . O2S O 0.0785(9) 0.1802(15) 0.6493(9) 0.062(3) Uani 1 1 d . . . O7 O 0.4565(8) 0.0912(14) 0.8425(8) 0.056(3) Uani 1 1 d . . . N1 N 0.2587(10) 0.0744(17) 0.7892(9) 0.049(3) Uani 1 1 d . . . N2 N 0.1979(9) 0.1140(13) 1.0685(8) 0.040(2) Uani 1 1 d . . . C1 C 0.2257(10) -0.0326(16) 0.6229(9) 0.039(2) Uani 1 1 d . . . C2 C 0.1853(13) -0.0937(19) 0.5300(11) 0.052(3) Uani 1 1 d . . . H2 H 0.1067 -0.1115 0.4935 0.062 Uiso 1 1 calc R . . C3 C 0.2683(16) -0.129(2) 0.4916(11) 0.059(4) Uani 1 1 d . . . H3 H 0.2447 -0.1716 0.4281 0.071 Uiso 1 1 calc R . . C4 C 0.3833(14) -0.101(2) 0.5466(12) 0.056(4) Uani 1 1 d . . . H4 H 0.4373 -0.1289 0.5210 0.068 Uiso 1 1 calc R . . C5 C 0.4196(12) -0.034(2) 0.6383(11) 0.054(3) Uani 1 1 d . . . H5 H 0.4974 -0.0085 0.6734 0.064 Uiso 1 1 calc R . . C6 C 0.3418(9) -0.0029(16) 0.6788(8) 0.037(2) Uani 1 1 d . . . C7 C 0.3644(11) 0.0624(17) 0.7809(10) 0.042(3) Uani 1 1 d . . . C21 C 0.2664(11) 0.0430(19) 1.1488(8) 0.043(3) Uani 1 1 d . . . H21 H 0.3370 0.0002 1.1529 0.052 Uiso 1 1 calc R . . C22 C 0.2379(13) 0.0278(19) 1.2311(9) 0.049(3) Uani 1 1 d . . . H22 H 0.2886 -0.0196 1.2901 0.059 Uiso 1 1 calc R . . C23 C 0.1280(13) 0.0888(18) 1.2183(12) 0.049(3) Uani 1 1 d . . . H23 H 0.1032 0.0762 1.2690 0.059 Uiso 1 1 calc R . . C24 C 0.0588(12) 0.164(2) 1.1354(11) 0.052(3) Uani 1 1 d . . . H24 H -0.0125 0.2077 1.1291 0.062 Uiso 1 1 calc R . . C25 C 0.0924(12) 0.1769(18) 1.0611(11) 0.049(3) Uani 1 1 d . . . H25 H 0.0436 0.2293 1.0031 0.059 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 I1 0.0436(5) 0.0418(5) 0.0345(5) -0.0014(3) 0.0153(3) 0.0002(3) S1 0.0325(13) 0.0533(18) 0.0397(15) -0.0064(13) 0.0097(11) 0.0005(12) O1S 0.054(6) 0.082(8) 0.063(7) -0.015(5) 0.033(5) -0.026(5) O2S 0.049(5) 0.055(6) 0.067(7) -0.004(5) 0.009(5) 0.016(5) O7 0.034(4) 0.072(7) 0.049(6) -0.014(5) 0.006(4) -0.011(4) N1 0.042(6) 0.067(7) 0.044(6) -0.009(5) 0.022(5) -0.002(5) N2 0.041(5) 0.038(5) 0.042(5) -0.003(4) 0.020(4) -0.002(4) C1 0.038(6) 0.035(6) 0.044(6) -0.003(5) 0.016(5) -0.003(5) C2 0.050(7) 0.058(8) 0.043(7) -0.011(6) 0.014(6) -0.007(6) C3 0.080(11) 0.058(9) 0.043(7) -0.013(6) 0.028(7) -0.001(8) C4 0.059(9) 0.064(9) 0.058(9) -0.002(7) 0.035(7) 0.004(7) C5 0.038(6) 0.072(10) 0.055(8) 0.010(7) 0.022(6) 0.002(6) C6 0.031(5) 0.042(6) 0.031(5) 0.003(4) 0.007(4) 0.002(4) C7 0.040(6) 0.045(6) 0.044(6) 0.003(5) 0.020(5) 0.002(5) C21 0.043(6) 0.060(8) 0.028(5) -0.005(5) 0.016(5) -0.002(6) C22 0.063(8) 0.055(8) 0.034(6) 0.014(6) 0.024(6) 0.006(6) C23 0.052(7) 0.049(7) 0.056(8) -0.006(6) 0.031(7) -0.008(6) C24 0.045(7) 0.053(8) 0.062(8) -0.008(7) 0.025(6) -0.001(6) C25 0.046(7) 0.040(7) 0.058(8) 0.002(6) 0.018(6) 0.007(5) _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 N1 2.254(11) . ? I1 N2 2.279(11) . ? S1 O1S 1.406(11) . ? S1 O2S 1.458(11) . ? S1 N1 1.611(12) . ? S1 C1 1.758(13) . ? O7 C7 1.178(16) . ? N1 C7 1.392(16) . ? N2 C21 1.285(17) . ? N2 C25 1.381(17) . ? C1 C2 1.352(19) . ? C1 C6 1.383(16) . ? C2 C3 1.41(2) . ? C2 H2 0.9300 . ? C3 C4 1.37(2) . ? C3 H3 0.9300 . ? C4 C5 1.36(2) . ? C4 H4 0.9300 . ? C5 C6 1.363(18) . ? C5 H5 0.9300 . ? C6 C7 1.516(17) . ? C21 C22 1.413(16) . ? C21 H21 0.9300 . ? C22 C23 1.40(2) . ? C22 H22 0.9300 . ? C23 C24 1.33(2) . ? C23 H23 0.9300 . ? C24 C25 1.34(2) . ? C24 H24 0.9300 . ? C25 H25 0.9300 . ? 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 N1 I1 N2 174.5(4) . . ? O1S S1 O2S 116.6(7) . . ? O1S S1 N1 111.2(7) . . ? O2S S1 N1 110.7(7) . . ? O1S S1 C1 111.8(7) . . ? O2S S1 C1 109.7(7) . . ? N1 S1 C1 94.8(6) . . ? C7 N1 S1 115.7(9) . . ? C7 N1 I1 125.2(9) . . ? S1 N1 I1 118.0(6) . . ? C21 N2 C25 119.6(12) . . ? C21 N2 I1 120.7(8) . . ? C25 N2 I1 119.1(9) . . ? C2 C1 C6 123.2(12) . . ? C2 C1 S1 128.2(11) . . ? C6 C1 S1 108.6(9) . . ? C1 C2 C3 116.5(13) . . ? C1 C2 H2 121.7 . . ? C3 C2 H2 121.7 . . ? C4 C3 C2 120.7(13) . . ? C4 C3 H3 119.7 . . ? C2 C3 H3 119.7 . . ? C5 C4 C3 120.8(14) . . ? C5 C4 H4 119.6 . . ? C3 C4 H4 119.6 . . ? C4 C5 C6 119.9(13) . . ? C4 C5 H5 120.0 . . ? C6 C5 H5 120.0 . . ? C5 C6 C1 118.8(12) . . ? C5 C6 C7 128.4(11) . . ? C1 C6 C7 112.7(10) . . ? O7 C7 N1 126.9(13) . . ? O7 C7 C6 125.1(12) . . ? N1 C7 C6 108.0(11) . . ? N2 C21 C22 122.1(12) . . ? N2 C21 H21 119.0 . . ? C22 C21 H21 119.0 . . ? C23 C22 C21 115.8(12) . . ? C23 C22 H22 122.1 . . ? C21 C22 H22 122.1 . . ? C24 C23 C22 121.5(13) . . ? C24 C23 H23 119.3 . . ? C22 C23 H23 119.3 . . ? C23 C24 C25 119.4(14) . . ? C23 C24 H24 120.3 . . ? C25 C24 H24 120.3 . . ? C24 C25 N2 121.6(13) . . ? C24 C25 H25 119.2 . . ? N2 C25 H25 119.2 . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 5.267 _refine_diff_density_min -2.448 _refine_diff_density_rms 0.267 #===END data_NISac2.Pyz _database_code_depnum_ccdc_archive 'CCDC 746493' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H12 I2 N4 O6 S2' _chemical_formula_weight 698.24 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' 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/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 9.1283(3) _cell_length_b 8.1398(2) _cell_length_c 14.4767(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.810(2) _cell_angle_gamma 90.00 _cell_volume 1075.55(5) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.156 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 668 _exptl_absorpt_coefficient_mu 3.163 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7859 _exptl_absorpt_correction_T_max 0.8329 _exptl_absorpt_process_details ; HKL SCALEPACK (Otwinowski & Minor, 1997) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'Nonius Kappa CCD diffractometer' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4685 _diffrn_reflns_av_R_equivalents 0.0114 _diffrn_reflns_av_sigmaI/netI 0.0198 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.35 _diffrn_reflns_theta_max 27.47 _reflns_number_total 2449 _reflns_number_gt 2279 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_cell_refinement 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0168P)^2^+1.0516P] 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 2449 _refine_ls_number_parameters 145 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0205 _refine_ls_R_factor_gt 0.0182 _refine_ls_wR_factor_ref 0.0443 _refine_ls_wR_factor_gt 0.0434 _refine_ls_goodness_of_fit_ref 1.125 _refine_ls_restrained_S_all 1.125 _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 I1 I 0.392232(14) 0.116082(16) -0.255962(8) 0.01620(6) Uani 1 1 d . . . S1 S 0.21124(5) 0.07804(6) -0.06060(3) 0.01539(11) Uani 1 1 d . . . O1S O 0.07717(17) 0.1571(2) -0.08857(11) 0.0239(3) Uani 1 1 d . . . O2S O 0.2170(2) -0.09652(19) -0.06992(12) 0.0266(4) Uani 1 1 d . . . O7 O 0.56328(17) 0.3067(2) -0.07983(11) 0.0254(4) Uani 1 1 d . . . N1 N 0.3514(2) 0.1644(2) -0.11315(12) 0.0187(4) Uani 1 1 d . . . N2 N 0.45713(19) 0.0507(2) -0.41343(12) 0.0163(3) Uani 1 1 d . . . C1 C 0.2684(2) 0.1445(2) 0.04976(14) 0.0153(4) Uani 1 1 d . . . C2 C 0.1957(2) 0.1249(3) 0.13212(15) 0.0186(4) Uani 1 1 d . . . H2 H 0.1076 0.0680 0.1352 0.022 Uiso 1 1 calc R . . C3 C 0.2609(2) 0.1945(3) 0.21032(15) 0.0205(4) Uani 1 1 d . . . H3 H 0.2151 0.1850 0.2670 0.025 Uiso 1 1 calc R . . C4 C 0.3934(2) 0.2781(3) 0.20505(15) 0.0216(4) Uani 1 1 d . . . H4 H 0.4357 0.3217 0.2585 0.026 Uiso 1 1 calc R . . C5 C 0.4637(2) 0.2976(3) 0.12087(15) 0.0206(4) Uani 1 1 d . . . H5 H 0.5519 0.3544 0.1174 0.025 Uiso 1 1 calc R . . C6 C 0.3990(2) 0.2302(3) 0.04262(14) 0.0159(4) Uani 1 1 d . . . C7 C 0.4516(2) 0.2405(3) -0.05459(14) 0.0175(4) Uani 1 1 d . . . C21 C 0.3654(2) 0.0615(3) -0.48631(15) 0.0177(4) Uani 1 1 d . . . H21 H 0.2717 0.1040 -0.4787 0.021 Uiso 1 1 calc R . . C22 C 0.4090(2) 0.0097(3) -0.57267(15) 0.0179(4) Uani 1 1 d . . . H22 H 0.3435 0.0172 -0.6223 0.021 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 I1 0.01807(8) 0.01860(8) 0.01195(8) -0.00055(4) 0.00120(5) 0.00061(5) S1 0.0167(2) 0.0168(2) 0.0127(2) -0.00090(18) 0.00055(18) -0.00240(19) O1S 0.0177(8) 0.0338(9) 0.0201(8) -0.0001(7) -0.0040(6) 0.0011(7) O2S 0.0400(10) 0.0165(8) 0.0235(9) -0.0041(6) 0.0030(7) -0.0051(7) O7 0.0206(8) 0.0366(9) 0.0192(8) -0.0004(7) 0.0033(6) -0.0083(7) N1 0.0205(9) 0.0254(9) 0.0104(8) -0.0032(7) 0.0032(7) -0.0051(8) N2 0.0198(9) 0.0149(8) 0.0142(8) -0.0014(7) 0.0023(7) 0.0010(7) C1 0.0170(10) 0.0152(9) 0.0136(9) -0.0001(8) -0.0008(7) 0.0020(8) C2 0.0185(10) 0.0210(11) 0.0163(10) 0.0034(8) 0.0022(8) 0.0015(8) C3 0.0224(11) 0.0265(11) 0.0126(10) 0.0023(8) 0.0024(8) 0.0067(9) C4 0.0240(11) 0.0260(11) 0.0147(10) -0.0024(8) -0.0053(8) 0.0051(9) C5 0.0174(10) 0.0255(11) 0.0189(11) -0.0030(9) -0.0017(8) -0.0008(8) C6 0.0161(9) 0.0179(10) 0.0138(10) -0.0004(8) 0.0007(7) 0.0023(8) C7 0.0177(10) 0.0205(10) 0.0143(10) -0.0006(8) 0.0005(8) 0.0005(8) C21 0.0172(10) 0.0163(9) 0.0195(10) -0.0010(8) 0.0008(8) 0.0023(8) C22 0.0203(10) 0.0187(10) 0.0146(10) -0.0009(8) -0.0023(8) 0.0007(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 N1 2.1423(17) . ? I1 N2 2.4227(17) . ? S1 O2S 1.4283(16) . ? S1 O1S 1.4358(16) . ? S1 N1 1.6544(18) . ? S1 C1 1.759(2) . ? O7 C7 1.214(3) . ? N1 C7 1.384(3) . ? N2 C22 1.335(3) 3_654 ? N2 C21 1.341(3) . ? C1 C2 1.382(3) . ? C1 C6 1.387(3) . ? C2 C3 1.392(3) . ? C2 H2 0.9300 . ? C3 C4 1.391(3) . ? C3 H3 0.9300 . ? C4 C5 1.394(3) . ? C4 H4 0.9300 . ? C5 C6 1.384(3) . ? C5 H5 0.9300 . ? C6 C7 1.496(3) . ? C21 C22 1.383(3) . ? C21 H21 0.9300 . ? C22 N2 1.335(3) 3_654 ? C22 H22 0.9300 . ? 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 N1 I1 N2 175.26(6) . . ? O2S S1 O1S 116.84(11) . . ? O2S S1 N1 110.45(10) . . ? O1S S1 N1 109.98(10) . . ? O2S S1 C1 112.40(10) . . ? O1S S1 C1 111.03(10) . . ? N1 S1 C1 93.76(9) . . ? C7 N1 S1 114.64(14) . . ? C7 N1 I1 123.41(14) . . ? S1 N1 I1 120.80(10) . . ? C22 N2 C21 117.94(18) 3_654 . ? C22 N2 I1 117.34(13) 3_654 . ? C21 N2 I1 124.59(14) . . ? C2 C1 C6 123.1(2) . . ? C2 C1 S1 127.49(17) . . ? C6 C1 S1 109.35(15) . . ? C1 C2 C3 116.7(2) . . ? C1 C2 H2 121.6 . . ? C3 C2 H2 121.6 . . ? C4 C3 C2 121.1(2) . . ? C4 C3 H3 119.4 . . ? C2 C3 H3 119.4 . . ? C3 C4 C5 121.0(2) . . ? C3 C4 H4 119.5 . . ? C5 C4 H4 119.5 . . ? C6 C5 C4 118.3(2) . . ? C6 C5 H5 120.9 . . ? C4 C5 H5 120.9 . . ? C5 C6 C1 119.74(19) . . ? C5 C6 C7 127.54(19) . . ? C1 C6 C7 112.70(18) . . ? O7 C7 N1 124.38(19) . . ? O7 C7 C6 126.14(19) . . ? N1 C7 C6 109.47(17) . . ? N2 C21 C22 120.44(19) . . ? N2 C21 H21 119.8 . . ? C22 C21 H21 119.8 . . ? N2 C22 C21 121.62(19) 3_654 . ? N2 C22 H22 119.2 3_654 . ? C21 C22 H22 119.2 . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.653 _refine_diff_density_min -0.577 _refine_diff_density_rms 0.083 #===END data_NBSac2.Pyz _database_code_depnum_ccdc_archive 'CCDC 746494' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H12 Br2 N4 O6 S2' _chemical_formula_weight 604.26 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 'P 21/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 7.78470(10) _cell_length_b 9.8956(2) _cell_length_c 14.0214(2) _cell_angle_alpha 90.00 _cell_angle_beta 96.2877(10) _cell_angle_gamma 90.00 _cell_volume 1073.63(3) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.869 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 596 _exptl_absorpt_coefficient_mu 4.015 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6896 _exptl_absorpt_correction_T_max 0.7947 _exptl_absorpt_process_details ; HKL SCALEPACK (Otwinowski & Minor, 1997) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'Nonius Kappa CCD diffractometer' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4719 _diffrn_reflns_av_R_equivalents 0.0105 _diffrn_reflns_av_sigmaI/netI 0.0169 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.53 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2449 _reflns_number_gt 2313 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_cell_refinement 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0293P)^2^+0.5749P] 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 2449 _refine_ls_number_parameters 145 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0229 _refine_ls_R_factor_gt 0.0212 _refine_ls_wR_factor_ref 0.0557 _refine_ls_wR_factor_gt 0.0547 _refine_ls_goodness_of_fit_ref 1.089 _refine_ls_restrained_S_all 1.089 _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 Br1 Br 0.10881(2) 0.082276(16) 0.750211(11) 0.02148(7) Uani 1 1 d . . . S1 S 0.26960(5) 0.05934(4) 0.55610(3) 0.01876(10) Uani 1 1 d . . . O1S O 0.44433(16) 0.08365(13) 0.59642(9) 0.0256(3) Uani 1 1 d . . . O2S O 0.21886(19) -0.07812(12) 0.53980(10) 0.0291(3) Uani 1 1 d . . . O7 O -0.05752(16) 0.31424(13) 0.61697(9) 0.0271(3) Uani 1 1 d . . . N1 N 0.1338(2) 0.13658(16) 0.62203(10) 0.0269(3) Uani 1 1 d . . . N2 N 0.44400(18) 0.52537(15) 0.58845(10) 0.0221(3) Uani 1 1 d . . . C1 C 0.2115(2) 0.16433(16) 0.45671(11) 0.0179(3) Uani 1 1 d . . . C2 C 0.2729(2) 0.15970(18) 0.36790(12) 0.0228(3) Uani 1 1 d . . . H2 H 0.3513 0.0940 0.3532 0.027 Uiso 1 1 calc R . . C3 C 0.2120(2) 0.25796(19) 0.30155(12) 0.0246(4) Uani 1 1 d . . . H3 H 0.2506 0.2582 0.2411 0.030 Uiso 1 1 calc R . . C4 C 0.0949(2) 0.35551(19) 0.32399(12) 0.0256(4) Uani 1 1 d . . . H4 H 0.0566 0.4203 0.2785 0.031 Uiso 1 1 calc R . . C5 C 0.0337(2) 0.35788(17) 0.41369(12) 0.0221(3) Uani 1 1 d . . . H5 H -0.0455 0.4229 0.4285 0.027 Uiso 1 1 calc R . . C6 C 0.0938(2) 0.26092(16) 0.48019(11) 0.0182(3) Uani 1 1 d . . . C7 C 0.0435(2) 0.24532(16) 0.57886(12) 0.0199(3) Uani 1 1 d . . . C21 C 0.5183(3) 0.40827(17) 0.57000(13) 0.0248(4) Uani 1 1 d . . . H21 H 0.5329 0.3425 0.6176 0.030 Uiso 1 1 calc R . . C22 C 0.5742(2) 0.38260(18) 0.48128(12) 0.0233(3) Uani 1 1 d . . . H22 H 0.6252 0.2999 0.4702 0.028 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 0.02364(11) 0.02514(11) 0.01641(10) 0.00522(6) 0.00556(7) 0.00281(6) S1 0.0198(2) 0.02002(19) 0.01701(19) 0.00150(14) 0.00469(15) 0.00381(14) O1S 0.0224(6) 0.0317(7) 0.0218(6) 0.0000(5) -0.0012(5) 0.0033(5) O2S 0.0319(7) 0.0204(6) 0.0356(8) 0.0017(5) 0.0062(6) -0.0001(5) O7 0.0331(7) 0.0271(7) 0.0233(6) 0.0041(5) 0.0134(5) 0.0103(5) N1 0.0332(8) 0.0312(8) 0.0184(7) 0.0095(6) 0.0123(6) 0.0145(7) N2 0.0257(7) 0.0245(7) 0.0165(6) -0.0042(6) 0.0046(5) -0.0006(6) C1 0.0184(7) 0.0195(7) 0.0159(7) -0.0002(6) 0.0026(6) -0.0016(6) C2 0.0200(8) 0.0310(9) 0.0182(8) -0.0039(7) 0.0049(6) 0.0004(7) C3 0.0236(8) 0.0376(10) 0.0131(7) -0.0004(7) 0.0044(6) -0.0066(7) C4 0.0274(9) 0.0315(9) 0.0176(8) 0.0063(7) 0.0009(6) -0.0036(7) C5 0.0240(8) 0.0222(8) 0.0206(8) 0.0029(6) 0.0050(6) 0.0020(6) C6 0.0189(7) 0.0205(8) 0.0155(7) 0.0004(6) 0.0040(6) -0.0006(6) C7 0.0231(8) 0.0196(8) 0.0179(7) 0.0033(6) 0.0056(6) 0.0030(6) C21 0.0323(10) 0.0229(8) 0.0192(8) 0.0017(6) 0.0021(7) 0.0016(7) C22 0.0264(9) 0.0204(8) 0.0231(8) -0.0047(7) 0.0027(6) 0.0043(7) _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 N1 1.9062(14) . ? S1 O2S 1.4279(13) . ? S1 O1S 1.4350(13) . ? S1 N1 1.6644(15) . ? S1 C1 1.7573(16) . ? O7 C7 1.209(2) . ? N1 C7 1.387(2) . ? N2 C22 1.332(2) 3_666 ? N2 C21 1.333(2) . ? C1 C2 1.383(2) . ? C1 C6 1.388(2) . ? C2 C3 1.393(2) . ? C2 H2 0.9300 . ? C3 C4 1.388(3) . ? C3 H3 0.9300 . ? C4 C5 1.393(2) . ? C4 H4 0.9300 . ? C5 C6 1.383(2) . ? C5 H5 0.9300 . ? C6 C7 1.487(2) . ? C21 C22 1.386(3) . ? C21 H21 0.9300 . ? C22 N2 1.332(2) 3_666 ? C22 H22 0.9300 . ? 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 O2S S1 O1S 117.15(8) . . ? O2S S1 N1 110.18(9) . . ? O1S S1 N1 109.66(8) . . ? O2S S1 C1 113.18(8) . . ? O1S S1 C1 111.35(8) . . ? N1 S1 C1 92.58(7) . . ? C7 N1 S1 115.85(11) . . ? C7 N1 Br1 122.06(11) . . ? S1 N1 Br1 122.07(8) . . ? C22 N2 C21 117.73(15) 3_666 . ? C2 C1 C6 122.60(15) . . ? C2 C1 S1 127.59(13) . . ? C6 C1 S1 109.77(12) . . ? C1 C2 C3 116.89(16) . . ? C1 C2 H2 121.6 . . ? C3 C2 H2 121.6 . . ? C4 C3 C2 121.23(15) . . ? C4 C3 H3 119.4 . . ? C2 C3 H3 119.4 . . ? C3 C4 C5 120.97(16) . . ? C3 C4 H4 119.5 . . ? C5 C4 H4 119.5 . . ? C6 C5 C4 118.23(16) . . ? C6 C5 H5 120.9 . . ? C4 C5 H5 120.9 . . ? C5 C6 C1 120.07(15) . . ? C5 C6 C7 126.53(15) . . ? C1 C6 C7 113.39(14) . . ? O7 C7 N1 124.59(15) . . ? O7 C7 C6 127.10(15) . . ? N1 C7 C6 108.31(13) . . ? N2 C21 C22 121.28(17) . . ? N2 C21 H21 119.4 . . ? C22 C21 H21 119.4 . . ? N2 C22 C21 120.99(16) 3_666 . ? N2 C22 H22 119.5 3_666 . ? C21 C22 H22 119.5 . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.277 _refine_diff_density_min -0.454 _refine_diff_density_rms 0.071 #===END data_NBSac _database_code_depnum_ccdc_archive 'CCDC 746495' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C7 H4 Br N O3 S' _chemical_formula_weight 262.08 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 'P 21/a' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 7.7944(2) _cell_length_b 28.4335(7) _cell_length_c 8.6973(2) _cell_angle_alpha 90.00 _cell_angle_beta 116.1549(12) _cell_angle_gamma 90.00 _cell_volume 1730.15(8) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.012 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1024 _exptl_absorpt_coefficient_mu 4.962 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5647 _exptl_absorpt_correction_T_max 0.6637 _exptl_absorpt_process_details ; HKL SCALEPACK (Otwinowski & Minor, 1997) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Nonius Kappa CCD diffractometer' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7625 _diffrn_reflns_av_R_equivalents 0.0218 _diffrn_reflns_av_sigmaI/netI 0.0316 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -36 _diffrn_reflns_limit_k_max 36 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.98 _diffrn_reflns_theta_max 27.49 _reflns_number_total 3955 _reflns_number_gt 3070 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_cell_refinement 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0320P)^2^+1.3738P] 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 3955 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0476 _refine_ls_R_factor_gt 0.0315 _refine_ls_wR_factor_ref 0.0795 _refine_ls_wR_factor_gt 0.0736 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _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 0.75510(5) 0.151189(11) 0.37061(4) 0.04250(10) Uani 1 1 d . . . S1 S 0.76216(11) 0.15744(3) 0.02338(9) 0.03493(17) Uani 1 1 d . . . O11S O 0.9341(3) 0.13346(9) 0.0563(3) 0.0516(6) Uani 1 1 d . . . O12S O 0.5896(3) 0.13099(8) -0.0470(3) 0.0491(5) Uani 1 1 d . . . O71 O 0.7413(4) 0.25830(8) 0.2950(3) 0.0515(6) Uani 1 1 d . . . N1 N 0.7836(4) 0.18561(9) 0.2032(3) 0.0407(6) Uani 1 1 d . . . C11 C 0.7418(4) 0.21093(10) -0.0823(4) 0.0329(6) Uani 1 1 d . . . C12 C 0.7267(4) 0.21666(12) -0.2458(4) 0.0427(7) Uani 1 1 d . . . H12 H 0.7281 0.1911 -0.3120 0.051 Uiso 1 1 calc R . . C13 C 0.7095(5) 0.26235(13) -0.3061(4) 0.0489(8) Uani 1 1 d . . . H13 H 0.6970 0.2676 -0.4162 0.059 Uiso 1 1 calc R . . C14 C 0.7104(5) 0.30016(13) -0.2075(4) 0.0511(8) Uani 1 1 d . . . H14 H 0.6996 0.3304 -0.2516 0.061 Uiso 1 1 calc R . . C15 C 0.7273(4) 0.29397(11) -0.0425(4) 0.0432(7) Uani 1 1 d . . . H15 H 0.7284 0.3196 0.0243 0.052 Uiso 1 1 calc R . . C16 C 0.7424(4) 0.24852(10) 0.0192(4) 0.0335(6) Uani 1 1 d . . . C17 C 0.7563(4) 0.23410(11) 0.1884(4) 0.0361(6) Uani 1 1 d . . . Br2 Br 0.30066(5) 0.148528(11) -0.56978(4) 0.04370(10) Uani 1 1 d . . . S2 S 0.22716(10) 0.05827(3) -0.41155(10) 0.03960(18) Uani 1 1 d . . . O21S O 0.1660(3) 0.08166(9) -0.3002(3) 0.0561(6) Uani 1 1 d . . . O22S O 0.0867(3) 0.04078(9) -0.5703(3) 0.0538(6) Uani 1 1 d . . . O72 O 0.6957(3) 0.10114(8) -0.3897(3) 0.0474(5) Uani 1 1 d . . . N2 N 0.3803(3) 0.09323(9) -0.4505(3) 0.0441(6) Uani 1 1 d . . . C21 C 0.4111(4) 0.01779(10) -0.3000(4) 0.0362(6) Uani 1 1 d . . . C22 C 0.3966(5) -0.02383(12) -0.2258(4) 0.0473(8) Uani 1 1 d . . . H22 H 0.2804 -0.0343 -0.2327 0.057 Uiso 1 1 calc R . . C23 C 0.5633(5) -0.04938(12) -0.1403(4) 0.0532(9) Uani 1 1 d . . . H23 H 0.5588 -0.0776 -0.0881 0.064 Uiso 1 1 calc R . . C24 C 0.7355(5) -0.03415(12) -0.1305(4) 0.0521(9) Uani 1 1 d . . . H24 H 0.8445 -0.0523 -0.0731 0.063 Uiso 1 1 calc R . . C25 C 0.7486(4) 0.00816(12) -0.2057(4) 0.0451(7) Uani 1 1 d . . . H25 H 0.8647 0.0186 -0.1991 0.054 Uiso 1 1 calc R . . C26 C 0.5839(4) 0.03393(10) -0.2898(4) 0.0351(6) Uani 1 1 d . . . C27 C 0.5691(4) 0.07935(11) -0.3787(3) 0.0360(6) 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 Br1 0.0583(2) 0.03982(18) 0.03537(17) 0.00155(13) 0.02612(15) -0.00616(14) S1 0.0444(4) 0.0321(4) 0.0308(4) -0.0027(3) 0.0188(3) -0.0023(3) O11S 0.0549(14) 0.0501(14) 0.0505(13) 0.0034(11) 0.0239(11) 0.0154(11) O12S 0.0565(14) 0.0414(13) 0.0489(12) -0.0057(11) 0.0226(11) -0.0148(11) O71 0.0823(18) 0.0390(13) 0.0457(13) -0.0101(10) 0.0395(13) -0.0075(11) N1 0.0639(17) 0.0345(14) 0.0321(12) 0.0006(10) 0.0289(12) -0.0039(12) C11 0.0347(15) 0.0321(15) 0.0334(14) 0.0001(12) 0.0164(12) -0.0041(12) C12 0.0491(18) 0.0489(19) 0.0338(15) -0.0043(14) 0.0216(14) -0.0078(15) C13 0.057(2) 0.058(2) 0.0339(16) 0.0071(15) 0.0218(15) -0.0082(17) C14 0.060(2) 0.044(2) 0.0487(19) 0.0133(16) 0.0226(17) -0.0046(16) C15 0.0516(19) 0.0330(17) 0.0498(18) -0.0013(14) 0.0268(16) -0.0052(14) C16 0.0349(16) 0.0343(16) 0.0330(14) 0.0004(11) 0.0164(13) -0.0037(12) C17 0.0430(17) 0.0347(16) 0.0347(15) -0.0017(13) 0.0209(13) -0.0043(13) Br2 0.04863(19) 0.04346(19) 0.03973(18) 0.00833(13) 0.02014(15) 0.00886(14) S2 0.0351(4) 0.0388(4) 0.0449(4) -0.0002(3) 0.0176(3) -0.0022(3) O21S 0.0544(14) 0.0579(16) 0.0644(15) -0.0033(12) 0.0338(12) 0.0096(12) O22S 0.0418(13) 0.0604(16) 0.0514(14) -0.0054(11) 0.0133(11) -0.0095(11) O72 0.0434(12) 0.0498(14) 0.0529(13) 0.0103(11) 0.0247(11) -0.0052(10) N2 0.0355(14) 0.0357(14) 0.0567(16) 0.0108(12) 0.0164(12) 0.0005(11) C21 0.0395(16) 0.0319(15) 0.0368(15) -0.0047(12) 0.0164(13) -0.0039(12) C22 0.051(2) 0.0398(18) 0.0518(19) -0.0004(15) 0.0235(16) -0.0095(15) C23 0.066(2) 0.0356(18) 0.0505(19) 0.0050(15) 0.0186(18) -0.0026(17) C24 0.052(2) 0.0402(19) 0.052(2) 0.0030(15) 0.0115(16) 0.0047(15) C25 0.0413(18) 0.0410(18) 0.0490(19) -0.0006(14) 0.0163(15) 0.0015(14) C26 0.0383(16) 0.0317(15) 0.0345(15) -0.0017(12) 0.0152(13) -0.0005(12) C27 0.0402(17) 0.0366(16) 0.0322(15) -0.0020(12) 0.0168(13) -0.0025(13) _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 N1 1.847(2) . ? S1 O11S 1.416(2) . ? S1 O12S 1.422(2) . ? S1 N1 1.699(2) . ? S1 C11 1.748(3) . ? O71 C17 1.201(3) . ? N1 C17 1.393(4) . ? C11 C12 1.384(4) . ? C11 C16 1.385(4) . ? C12 C13 1.385(5) . ? C12 H12 0.9300 . ? C13 C14 1.373(5) . ? C13 H13 0.9300 . ? C14 C15 1.393(4) . ? C14 H14 0.9300 . ? C15 C16 1.384(4) . ? C15 H15 0.9300 . ? C16 C17 1.485(4) . ? Br2 N2 1.835(3) . ? S2 O21S 1.419(2) . ? S2 O22S 1.421(2) . ? S2 N2 1.699(3) . ? S2 C21 1.759(3) . ? O72 C27 1.203(3) . ? N2 C27 1.379(4) . ? C21 C22 1.376(4) . ? C21 C26 1.388(4) . ? C22 C23 1.384(5) . ? C22 H22 0.9300 . ? C23 C24 1.377(5) . ? C23 H23 0.9300 . ? C24 C25 1.394(5) . ? C24 H24 0.9300 . ? C25 C26 1.375(4) . ? C25 H25 0.9300 . ? C26 C27 1.483(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 O11S S1 O12S 117.62(15) . . ? O11S S1 N1 109.94(14) . . ? O12S S1 N1 109.64(13) . . ? O11S S1 C11 112.56(14) . . ? O12S S1 C11 112.60(14) . . ? N1 S1 C11 91.33(13) . . ? C17 N1 S1 115.63(19) . . ? C17 N1 Br1 122.08(19) . . ? S1 N1 Br1 118.60(15) . . ? C12 C11 C16 122.6(3) . . ? C12 C11 S1 126.1(2) . . ? C16 C11 S1 111.2(2) . . ? C11 C12 C13 116.7(3) . . ? C11 C12 H12 121.6 . . ? C13 C12 H12 121.6 . . ? C14 C13 C12 121.6(3) . . ? C14 C13 H13 119.2 . . ? C12 C13 H13 119.2 . . ? C13 C14 C15 121.1(3) . . ? C13 C14 H14 119.4 . . ? C15 C14 H14 119.4 . . ? C16 C15 C14 118.1(3) . . ? C16 C15 H15 121.0 . . ? C14 C15 H15 121.0 . . ? C15 C16 C11 119.8(3) . . ? C15 C16 C17 126.8(3) . . ? C11 C16 C17 113.4(2) . . ? O71 C17 N1 124.0(3) . . ? O71 C17 C16 128.1(3) . . ? N1 C17 C16 107.9(2) . . ? O21S S2 O22S 118.71(15) . . ? O21S S2 N2 109.81(15) . . ? O22S S2 N2 108.61(14) . . ? O21S S2 C21 111.57(14) . . ? O22S S2 C21 113.47(15) . . ? N2 S2 C21 91.10(13) . . ? C27 N2 S2 116.5(2) . . ? C27 N2 Br2 121.9(2) . . ? S2 N2 Br2 121.46(14) . . ? C22 C21 C26 122.2(3) . . ? C22 C21 S2 127.3(2) . . ? C26 C21 S2 110.5(2) . . ? C21 C22 C23 116.8(3) . . ? C21 C22 H22 121.6 . . ? C23 C22 H22 121.6 . . ? C24 C23 C22 121.8(3) . . ? C24 C23 H23 119.1 . . ? C22 C23 H23 119.1 . . ? C23 C24 C25 120.9(3) . . ? C23 C24 H24 119.6 . . ? C25 C24 H24 119.6 . . ? C26 C25 C24 117.7(3) . . ? C26 C25 H25 121.1 . . ? C24 C25 H25 121.1 . . ? C25 C26 C21 120.6(3) . . ? C25 C26 C27 125.5(3) . . ? C21 C26 C27 113.8(3) . . ? O72 C27 N2 124.4(3) . . ? O72 C27 C26 127.7(3) . . ? N2 C27 C26 107.9(2) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.721 _refine_diff_density_min -0.556 _refine_diff_density_rms 0.070 #===END