# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2014 ####################################################################### # # 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_1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C2 H10 I2 N4 O S2' _chemical_formula_weight 424.06 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 '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 ccn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z' 'x+1/2, -y, -z+1/2' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z' '-x-1/2, y, z-1/2' 'x, -y-1/2, z-1/2' _cell_length_a 16.3810(5) _cell_length_b 5.10600(10) _cell_length_c 13.3220(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1114.27(5) _cell_formula_units_Z 4 _cell_measurement_temperature 120.00(10) _cell_measurement_reflns_used 2060 _cell_measurement_theta_min 5.3880 _cell_measurement_theta_max 75.3060 _exptl_crystal_description block _exptl_crystal_colour 'light yellow' _exptl_crystal_size_max 0.04 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.528 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_absorpt_coefficient_mu 47.573 _exptl_absorpt_correction_T_min 0.62663 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET) (compiled Dec 3 2012,18:21:49) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 120.00(10) _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_source 'SuperNova (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'SuperNova, Single source at offset), Atlas' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.5357 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2598 _diffrn_reflns_av_R_equivalents 0.0180 _diffrn_reflns_av_sigmaI/netI 0.0194 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 2 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 5.40 _diffrn_reflns_theta_max 75.46 _reflns_number_total 1128 _reflns_number_gt 1068 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET) (compiled Dec 3 2012,18:21:49) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET) (compiled Dec 3 2012,18:21:49) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET) (compiled Dec 3 2012,18:21:49) ; _computing_structure_solution ? _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^)+(0.0379P)^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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00058(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1128 _refine_ls_number_parameters 56 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0230 _refine_ls_R_factor_gt 0.0218 _refine_ls_wR_factor_ref 0.0590 _refine_ls_wR_factor_gt 0.0581 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.064 _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 I1 I 0.578081(12) 0.06768(4) 0.146253(14) 0.01075(12) Uani 1 1 d . . . S1 S 0.71988(5) 0.57691(14) 0.01254(6) 0.00800(18) Uani 1 1 d . . . C1 C 0.64034(18) 0.6311(6) -0.0764(2) 0.0091(6) Uani 1 1 d . . . N11 N 0.64232(17) 0.8258(5) -0.13986(19) 0.0105(5) Uani 1 1 d . . . H11B H 0.6043 0.8425 -0.1840 0.013 Uiso 1 1 calc R . . H11A H 0.6816 0.9374 -0.1376 0.013 Uiso 1 1 calc R . . N12 N 0.58288(16) 0.4539(5) -0.0750(2) 0.0117(6) Uani 1 1 d . . . H12A H 0.5435 0.4617 -0.1176 0.014 Uiso 1 1 calc R . . H12B H 0.5844 0.3294 -0.0316 0.014 Uiso 1 1 calc R . . O1W O 0.7500 1.2500 -0.2110(2) 0.0134(6) Uani 1 2 d S . . H1W H 0.790(2) 1.192(9) -0.252(3) 0.021(11) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 I1 0.00826(16) 0.01674(17) 0.00726(16) 0.00251(7) -0.00003(6) 0.00118(6) S1 0.0078(3) 0.0086(4) 0.0077(3) 0.0017(2) -0.0011(3) -0.0003(2) C1 0.0079(13) 0.0131(14) 0.0063(13) -0.0021(12) 0.0027(12) 0.0045(12) N11 0.0096(12) 0.0130(14) 0.0090(12) 0.0016(10) -0.0028(10) -0.0016(11) N12 0.0093(13) 0.0134(15) 0.0123(15) 0.0004(11) -0.0014(10) -0.0017(9) O1W 0.0103(15) 0.0189(16) 0.0109(14) 0.000 0.000 0.0030(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 S1 C1 1.783(3) . ? S1 S1 2.0244(14) 2_665 ? C1 N11 1.305(4) . ? C1 N12 1.306(4) . ? N11 H11B 0.8600 . ? N11 H11A 0.8600 . ? N12 H12A 0.8600 . ? N12 H12B 0.8600 . ? O1W H1W 0.90(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 C1 S1 S1 102.75(12) . 2_665 ? N11 C1 N12 123.7(3) . . ? N11 C1 S1 122.0(2) . . ? N12 C1 S1 114.2(3) . . ? C1 N11 H11B 120.0 . . ? C1 N11 H11A 120.0 . . ? H11B N11 H11A 120.0 . . ? C1 N12 H12A 120.0 . . ? C1 N12 H12B 120.0 . . ? H12A N12 H12B 120.0 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag S1 S1 C1 N11 16.1(3) 2_665 . . . ? S1 S1 C1 N12 -166.8(2) 2_665 . . . ? 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 N11 H11B I1 0.86 3.06 3.652(3) 127.5 5_665 N11 H11B I1 0.86 3.06 3.652(3) 127.5 5_665 N11 H11A O1W 0.86 2.18 2.950(3) 148.5 . N11 H11A S1 0.86 2.57 3.076(3) 118.6 2_665 N12 H12A I1 0.86 3.14 3.717(3) 126.2 5_665 N12 H12A I1 0.86 3.14 3.717(3) 126.2 5_665 N12 H12B I1 0.86 2.72 3.548(3) 161.3 . O1W H1W I1 0.90(4) 2.63(4) 3.5231(17) 171(4) 7_765 _diffrn_measured_fraction_theta_max 0.969 _diffrn_reflns_theta_full 75.46 _diffrn_measured_fraction_theta_full 0.969 _refine_diff_density_max 0.786 _refine_diff_density_min -1.079 _refine_diff_density_rms 0.146 _database_code_depnum_ccdc_archive 'CCDC 924828' ####################################################################### # # 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_2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C2 H8 N4 S2), I3, 2(I), Cl' _chemical_formula_sum 'C4 H16 Cl I5 N8 S4' _chemical_formula_weight 974.44 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 '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 9.6516(3) _cell_length_b 9.7546(2) _cell_length_c 13.8230(5) _cell_angle_alpha 90.00 _cell_angle_beta 109.653(4) _cell_angle_gamma 90.00 _cell_volume 1225.59(6) _cell_formula_units_Z 2 _cell_measurement_temperature 129.9(2) _cell_measurement_reflns_used 5739 _cell_measurement_theta_min 3.3923 _cell_measurement_theta_max 75.4687 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.04 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.641 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 884 _exptl_absorpt_coefficient_mu 54.076 _exptl_absorpt_correction_T_min 0.32243 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 129.9(2) _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_source 'SuperNova (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'SuperNova, Single source at offset), Atlas' _diffrn_detector_area_resol_mean 10.5357 _diffrn_measurement_method '\w scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3685 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0097 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 4.91 _diffrn_reflns_theta_max 75.71 _reflns_number_total 3685 _reflns_number_gt 3404 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_structure_solution ? _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^)+(0.0994P)^2^+2.4648P] 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 3685 _refine_ls_number_parameters 104 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0467 _refine_ls_R_factor_gt 0.0444 _refine_ls_wR_factor_ref 0.1378 _refine_ls_wR_factor_gt 0.1355 _refine_ls_goodness_of_fit_ref 1.099 _refine_ls_restrained_S_all 1.099 _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 I1 I 0.16085(5) 0.25926(3) 0.61089(3) 0.01917(15) Uani 1 1 d . . . Cl1 Cl 0.5000 0.5000 0.5000 0.0203(4) Uani 1 2 d S . . S1 S 0.10191(17) 0.18825(14) 0.21745(11) 0.0229(3) Uani 1 1 d . . . N11 N -0.0305(6) -0.0450(5) 0.2183(4) 0.0226(10) Uani 1 1 d . . . H11B H -0.0655 -0.1128 0.2424 0.027 Uiso 1 1 calc R . . H11A H -0.0382 -0.0437 0.1545 0.027 Uiso 1 1 calc R . . C1 C 0.0344(7) 0.0561(6) 0.2785(4) 0.0198(11) Uani 1 1 d . . . I2 I 0.5000 0.0000 0.5000 0.02527(17) Uani 1 2 d S . . S2 S 0.22286(16) 0.30603(14) 0.33811(11) 0.0234(3) Uani 1 1 d . . . N12 N 0.0492(7) 0.0594(5) 0.3758(4) 0.0268(11) Uani 1 1 d . . . H12A H 0.0155 -0.0066 0.4026 0.032 Uiso 1 1 calc R . . H12B H 0.0926 0.1277 0.4131 0.032 Uiso 1 1 calc R . . C2 C 0.0968(7) 0.4357(6) 0.3446(4) 0.0194(11) Uani 1 1 d . . . I3 I 0.29636(4) -0.16236(4) 0.56926(3) 0.02805(15) Uani 1 1 d . . . N21 N -0.0448(6) 0.4295(6) 0.2918(4) 0.0283(11) Uani 1 1 d . . . H21A H -0.1025 0.4940 0.2971 0.034 Uiso 1 1 calc R . . H21B H -0.0796 0.3609 0.2519 0.034 Uiso 1 1 calc R . . N22 N 0.1557(6) 0.5367(5) 0.4061(4) 0.0219(10) Uani 1 1 d . . . H22A H 0.1017 0.6032 0.4135 0.026 Uiso 1 1 calc R . . H22B H 0.2487 0.5370 0.4393 0.026 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 0.0214(3) 0.0203(2) 0.0157(3) 0.00028(11) 0.00621(19) 0.00184(11) Cl1 0.0198(10) 0.0293(9) 0.0112(8) -0.0015(8) 0.0044(7) 0.0020(8) S1 0.0317(7) 0.0223(7) 0.0181(6) -0.0038(5) 0.0127(6) -0.0064(5) N11 0.033(3) 0.018(2) 0.018(2) -0.0007(18) 0.011(2) -0.005(2) C1 0.025(3) 0.019(3) 0.017(2) 0.000(2) 0.008(2) 0.004(2) I2 0.0285(4) 0.0220(3) 0.0227(3) -0.0016(2) 0.0052(2) 0.0045(2) S2 0.0212(7) 0.0223(7) 0.0266(7) -0.0064(5) 0.0080(5) -0.0009(5) N12 0.045(3) 0.022(2) 0.016(2) -0.0036(19) 0.013(2) -0.008(2) C2 0.022(3) 0.020(3) 0.016(2) 0.001(2) 0.005(2) -0.002(2) I3 0.0330(3) 0.0216(2) 0.0279(2) 0.00037(13) 0.00799(18) 0.00281(13) N21 0.021(3) 0.027(3) 0.031(3) -0.008(2) 0.001(2) 0.000(2) N22 0.018(2) 0.021(2) 0.022(2) -0.0034(19) 0.0001(19) -0.0003(18) _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 1.780(6) . ? S1 S2 2.038(2) . ? N11 C1 1.307(8) . ? C1 N12 1.303(7) . ? I2 I3 2.9246(4) 3_656 ? I2 I3 2.9246(4) . ? S2 C2 1.778(6) . ? C2 N22 1.300(8) . ? C2 N21 1.316(8) . ? 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 S2 102.7(2) . . ? N12 C1 N11 122.6(6) . . ? N12 C1 S1 122.7(5) . . ? N11 C1 S1 114.7(4) . . ? I3 I2 I3 180.0 3_656 . ? C2 S2 S1 103.2(2) . . ? N22 C2 N21 122.8(6) . . ? N22 C2 S2 114.6(5) . . ? N21 C2 S2 122.6(5) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag S2 S1 C1 N12 8.9(6) . . . . ? S2 S1 C1 N11 -170.7(4) . . . . ? C1 S1 S2 C2 -94.5(3) . . . . ? S1 S2 C2 N22 -169.5(4) . . . . ? S1 S2 C2 N21 10.7(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 N11 H11B I1 0.86 2.87 3.678(5) 156.6 3_556 N11 H11B I3 0.86 3.19 3.587(5) 110.9 4 N11 H11A Cl1 0.86 2.33 3.159(5) 163.5 2_545 N12 H12A I1 0.86 2.96 3.749(5) 152.6 3_556 N12 H12B S2 0.86 2.56 3.075(6) 119.3 . N12 H12B I1 0.86 2.89 3.629(5) 145.3 . N21 H21A I1 0.86 2.86 3.646(6) 152.0 3_566 N21 H21B S1 0.86 2.59 3.095(6) 118.8 . N21 H21B I1 0.86 2.86 3.597(5) 145.1 4_565 N22 H22A I1 0.86 2.79 3.587(5) 155.9 3_566 N22 H22A I3 0.86 3.27 3.673(5) 111.7 1_565 N22 H22B Cl1 0.86 2.31 3.155(5) 166.5 . _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 70.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 2.743 _refine_diff_density_min -1.399 _refine_diff_density_rms 0.276 _database_code_depnum_ccdc_archive 'CCDC 924829' ####################################################################### # # 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_3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C H5 N2 S, I3' _chemical_formula_sum 'C H5 I3 N2 S' _chemical_formula_weight 457.83 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' I I -0.4742 1.8119 '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 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.5529(2) _cell_length_b 13.2275(4) _cell_length_c 9.1452(2) _cell_angle_alpha 90.00 _cell_angle_beta 98.689(2) _cell_angle_gamma 90.00 _cell_volume 903.17(4) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 1515 _cell_measurement_theta_min 2.8955 _cell_measurement_theta_max 28.7848 _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 3.367 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 800 _exptl_absorpt_coefficient_mu 10.530 _exptl_absorpt_correction_T_min 0.78060 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(2) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_detector_area_resol_mean 16.1544 _diffrn_measurement_method '\w scans' _diffrn_reflns_number 10478 _diffrn_reflns_av_R_equivalents 0.0222 _diffrn_reflns_av_sigmaI/netI 0.0160 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.08 _diffrn_reflns_theta_max 28.27 _reflns_number_total 2060 _reflns_number_gt 1931 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_structure_solution ? _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^ > 2\s(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^)+(0.0151P)^2^+0.7058P] 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 2060 _refine_ls_number_parameters 64 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0196 _refine_ls_R_factor_gt 0.0167 _refine_ls_wR_factor_ref 0.0383 _refine_ls_wR_factor_gt 0.0376 _refine_ls_goodness_of_fit_ref 1.180 _refine_ls_restrained_S_all 1.180 _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 I1 I 0.36229(3) 0.387702(16) -0.24455(2) 0.01615(6) Uani 1 1 d . . . I2 I 0.24141(2) 0.400240(14) 0.03609(2) 0.01394(6) Uani 1 1 d . . . I3 I 0.12013(3) 0.414820(15) 0.33253(2) 0.01512(6) Uani 1 1 d . . . C1 C 0.7626(4) 0.2304(2) 0.0636(3) 0.0152(6) Uani 1 1 d . . . S1 S 0.62814(10) 0.15068(6) -0.05726(9) 0.02006(18) Uani 1 1 d . . . H1 H 0.5211 0.2203 -0.1125 0.024 Uiso 1 1 d R . . N11 N 0.8826(3) 0.1906(2) 0.1670(3) 0.0200(6) Uani 1 1 d . . . H11A H 0.9059 0.1288 0.1732 0.024 Uiso 1 1 d R . . H11B H 0.9572 0.2315 0.2191 0.024 Uiso 1 1 d R . . N12 N 0.7413(3) 0.3282(2) 0.0516(3) 0.0200(6) Uani 1 1 d . . . H12A H 0.6640 0.3550 -0.0183 0.024 Uiso 1 1 d R . . H12B H 0.8030 0.3678 0.1058 0.024 Uiso 1 1 d 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 0.01624(11) 0.01829(12) 0.01322(11) 0.00208(8) 0.00003(8) 0.00003(8) I2 0.01322(10) 0.01172(10) 0.01583(11) 0.00035(7) -0.00118(8) 0.00004(7) I3 0.01602(10) 0.01509(11) 0.01382(11) -0.00266(8) 0.00082(8) -0.00039(7) C1 0.0122(14) 0.0169(16) 0.0165(16) -0.0004(13) 0.0023(11) -0.0015(12) S1 0.0181(4) 0.0198(4) 0.0207(4) -0.0045(3) -0.0024(3) -0.0018(3) N11 0.0196(13) 0.0130(14) 0.0245(15) 0.0003(11) -0.0056(11) -0.0007(11) N12 0.0188(13) 0.0139(14) 0.0239(15) 0.0003(11) -0.0081(11) -0.0004(11) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 I2 2.8558(3) . ? I2 I3 2.9961(3) . ? C1 N12 1.307(4) . ? C1 N11 1.317(4) . ? C1 S1 1.739(3) . ? S1 H1 1.2781 . ? N11 H11A 0.8362 . ? N11 H11B 0.8689 . ? N12 H12A 0.8721 . ? N12 H12B 0.8170 . ? 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 I1 I2 I3 179.102(9) . . ? N12 C1 N11 121.2(3) . . ? N12 C1 S1 119.6(2) . . ? N11 C1 S1 119.1(2) . . ? C1 S1 H1 95.1 . . ? C1 N11 H11A 123.7 . . ? C1 N11 H11B 117.7 . . ? H11A N11 H11B 117.3 . . ? C1 N12 H12A 121.5 . . ? C1 N12 H12B 122.1 . . ? H12A N12 H12B 116.3 . . ? 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 S1 H1 I1 1.28 2.71 3.9694(9) 167.1 . N11 H11A I3 0.84 2.84 3.648(3) 163.8 2_645 N11 H11B I3 0.87 2.84 3.672(3) 159.9 1_655 N12 H12B I3 0.82 2.99 3.726(2) 151.6 1_655 N12 H12A I1 0.87 2.87 3.715(2) 163.6 . _diffrn_measured_fraction_theta_max 0.921 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.722 _refine_diff_density_min -0.776 _refine_diff_density_rms 0.134 _database_code_depnum_ccdc_archive 'CCDC 939693' ####################################################################### # # 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_4 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C2 H8 Br I3 N4 S2' _chemical_formula_weight 612.85 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M ' P21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.8698(2) _cell_length_b 12.0775(3) _cell_length_c 12.9332(3) _cell_angle_alpha 90.00 _cell_angle_beta 109.830(3) _cell_angle_gamma 90.00 _cell_volume 1450.25(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 9837 _cell_measurement_theta_min 3.6300 _cell_measurement_theta_max 75.3398 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.807 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1096 _exptl_absorpt_coefficient_mu 56.464 _exptl_absorpt_correction_T_min 0.28518 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_source 'SuperNova (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'SuperNova, Single source at offset), Atlas' _diffrn_detector_area_resol_mean 10.5357 _diffrn_measurement_method '\w scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13296 _diffrn_reflns_av_R_equivalents 0.0543 _diffrn_reflns_av_sigmaI/netI 0.0281 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 4.76 _diffrn_reflns_theta_max 75.51 _reflns_number_total 2968 _reflns_number_gt 2800 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_structure_solution ? _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^)+(0.0781P)^2^+3.2519P] 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 SHELXL _refine_ls_extinction_coef 0.00056(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2968 _refine_ls_number_parameters 113 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0443 _refine_ls_R_factor_gt 0.0427 _refine_ls_wR_factor_ref 0.1179 _refine_ls_wR_factor_gt 0.1160 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _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 I3 I 0.5000 0.5000 0.5000 0.04113(18) Uani 1 2 d S . . I1 I 1.0000 1.0000 0.5000 0.04588(19) Uani 1 2 d S . . I4 I 0.21712(5) 0.45394(4) 0.51501(4) 0.05226(18) Uani 1 1 d . . . I2 I 0.72497(7) 0.91609(5) 0.35185(5) 0.0688(2) Uani 1 1 d . . . Br1 Br 0.18927(6) 0.77519(5) 0.30369(5) 0.03943(19) Uani 1 1 d . . . S2 S 0.53191(14) 0.83914(13) 0.55222(11) 0.0392(3) Uani 1 1 d . . . S1 S 0.66532(15) 0.95840(11) 0.64194(13) 0.0405(3) Uani 1 1 d . . . N1 N 0.9369(5) 0.9493(5) 0.7578(5) 0.0449(12) Uani 1 1 d . . . H1A H 1.0215 0.9211 0.7863 0.054 Uiso 1 1 calc R . . H1B H 0.9229 1.0181 0.7682 0.054 Uiso 1 1 calc R . . N4 N 0.3050(6) 0.7595(5) 0.5856(5) 0.0471(12) Uani 1 1 d . . . H4A H 0.2497 0.7400 0.6214 0.056 Uiso 1 1 calc R . . H4B H 0.2773 0.7505 0.5155 0.056 Uiso 1 1 calc R . . N3 N 0.4769(5) 0.8180(6) 0.7441(4) 0.0475(13) Uani 1 1 d . . . H3B H 0.4240 0.7992 0.7821 0.057 Uiso 1 1 calc R . . H3A H 0.5604 0.8467 0.7761 0.057 Uiso 1 1 calc R . . N2 N 0.8451(7) 0.7845(5) 0.6806(7) 0.0655(19) Uani 1 1 d . . . H2B H 0.9282 0.7536 0.7080 0.079 Uiso 1 1 calc R . . H2A H 0.7723 0.7463 0.6413 0.079 Uiso 1 1 calc R . . C2 C 0.4302(6) 0.8027(4) 0.6372(5) 0.0325(10) Uani 1 1 d . . . C1 C 0.8297(6) 0.8876(5) 0.6986(4) 0.0340(11) 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 I3 0.0463(3) 0.0457(3) 0.0251(3) 0.00288(19) 0.0040(2) 0.0084(2) I1 0.0589(4) 0.0490(3) 0.0383(3) 0.0044(2) 0.0277(3) 0.0050(2) I4 0.0450(3) 0.0678(3) 0.0400(3) 0.00263(18) 0.00909(19) -0.00023(18) I2 0.0710(4) 0.0664(3) 0.0616(3) -0.0141(2) 0.0129(3) 0.0007(2) Br1 0.0271(3) 0.0503(4) 0.0372(3) -0.0098(2) 0.0061(2) -0.0074(2) S2 0.0314(6) 0.0510(8) 0.0279(6) -0.0050(6) 0.0006(5) -0.0110(5) S1 0.0267(6) 0.0359(7) 0.0440(8) -0.0006(6) -0.0074(5) -0.0005(5) N1 0.025(2) 0.066(3) 0.037(3) -0.011(2) 0.001(2) -0.006(2) N4 0.032(2) 0.063(3) 0.042(3) -0.008(3) 0.007(2) -0.012(2) N3 0.030(2) 0.075(4) 0.028(2) 0.000(2) -0.0023(19) -0.005(2) N2 0.034(3) 0.043(3) 0.101(6) 0.001(3) -0.001(3) 0.004(2) C2 0.025(2) 0.034(2) 0.033(3) 0.001(2) 0.003(2) 0.0038(19) C1 0.028(2) 0.047(3) 0.024(2) 0.007(2) 0.004(2) -0.003(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I3 I4 2.9172(5) 3_666 ? I3 I4 2.9172(5) . ? I1 I2 2.9220(6) 3_776 ? I1 I2 2.9220(6) . ? S2 C2 1.777(6) . ? S2 S1 2.0294(19) . ? S1 C1 1.759(6) . ? N1 C1 1.308(8) . ? N4 C2 1.298(8) . ? N3 C2 1.313(8) . ? N2 C1 1.286(9) . ? 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 I4 I3 I4 180.0 3_666 . ? I2 I1 I2 180.0 3_776 . ? C2 S2 S1 102.4(2) . . ? C1 S1 S2 102.8(2) . . ? N4 C2 N3 122.1(6) . . ? N4 C2 S2 114.8(5) . . ? N3 C2 S2 123.1(4) . . ? N2 C1 N1 122.4(6) . . ? N2 C1 S1 123.0(5) . . ? N1 C1 S1 114.6(5) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2 S2 S1 C1 102.7(3) . . . . ? S1 S2 C2 N4 155.8(4) . . . . ? S1 S2 C2 N3 -24.0(6) . . . . ? S2 S1 C1 N2 -0.4(7) . . . . ? S2 S1 C1 N1 177.4(4) . . . . ? C2 S2 S1 C1 102.7(3) . . . . ? S1 S2 C2 N4 155.8(4) . . . . ? S1 S2 C2 N3 -24.0(6) . . . . ? S2 S1 C1 N2 -0.4(7) . . . . ? S2 S1 C1 N1 177.4(4) . . . . ? 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 N1 H1A Br1 0.86 2.86 3.592(6) 144.6 4_676 N1 H1A I4 0.86 3.30 3.720(5) 113.0 4_676 N1 H1B Br1 0.86 2.76 3.547(6) 152.6 3_676 N4 H4A Br1 0.86 2.63 3.409(6) 151.8 4_576 N4 H4B Br1 0.86 2.60 3.436(6) 166.1 . N3 H3B Br1 0.86 2.59 3.377(6) 153.2 4_576 N3 H3A S1 0.86 2.67 3.122(6) 114.3 . N3 H3A I4 0.86 3.13 3.891(5) 149.4 2_656 N2 H2B Br1 0.86 2.48 3.305(6) 162.2 4_676 N2 H2A S2 0.86 2.52 3.044(6) 120.0 . N2 H2A I4 0.86 3.18 3.744(7) 125.7 3_666 _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 70.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.771 _refine_diff_density_min -1.667 _refine_diff_density_rms 0.234 _database_code_depnum_ccdc_archive 'CCDC 924830' ####################################################################### # # 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_5 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C2 H10 Br2 N4 O S2' _chemical_formula_weight 330.08 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.6763 1.2805 '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 2/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _cell_length_a 8.6389(11) _cell_length_b 5.0436(6) _cell_length_c 12.3817(16) _cell_angle_alpha 90.00 _cell_angle_beta 99.551(12) _cell_angle_gamma 90.00 _cell_volume 532.01(12) _cell_formula_units_Z 2 _cell_measurement_temperature 130.00(10) _cell_measurement_reflns_used 1817 _cell_measurement_theta_min 3.6169 _cell_measurement_theta_max 75.5721 _exptl_crystal_description block _exptl_crystal_colour ? _exptl_crystal_size_max 0.05 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.061 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 320 _exptl_absorpt_coefficient_mu 13.053 _exptl_absorpt_correction_T_min 0.53194 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 130.00(10) _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_source 'SuperNova (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'SuperNova, Single source at offset), Atlas' _diffrn_detector_area_resol_mean 10.5357 _diffrn_measurement_method '\w scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3184 _diffrn_reflns_av_R_equivalents 0.0270 _diffrn_reflns_av_sigmaI/netI 0.0204 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 5.19 _diffrn_reflns_theta_max 75.75 _reflns_number_total 1098 _reflns_number_gt 1047 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_structure_solution ? _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^)+(0.0813P)^2^+0.3595P] 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 SHELXL _refine_ls_extinction_coef 0.0042(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1098 _refine_ls_number_parameters 56 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0406 _refine_ls_R_factor_gt 0.0396 _refine_ls_wR_factor_ref 0.1221 _refine_ls_wR_factor_gt 0.1210 _refine_ls_goodness_of_fit_ref 1.185 _refine_ls_restrained_S_all 1.185 _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 Br1 Br 0.29414(4) 0.36609(7) 0.57304(3) 0.0308(3) Uani 1 1 d . . . S1 S -0.11833(12) -0.16010(18) 0.74556(9) 0.0358(3) Uani 1 1 d . . . O1W O 0.5000 0.7817(11) 0.7500 0.0432(10) Uani 1 2 d S . . N12 N -0.0824(4) 0.2159(8) 0.5936(3) 0.0394(8) Uani 1 1 d . . . H12B H -0.1167 0.3347 0.5458 0.047 Uiso 1 1 calc R . . H12A H 0.0161 0.1787 0.6067 0.047 Uiso 1 1 calc R . . C1 C -0.1806(5) 0.0908(7) 0.6466(4) 0.0343(8) Uani 1 1 d . . . N11 N -0.3320(4) 0.1377(6) 0.6307(3) 0.0406(9) Uani 1 1 d . . . H11B H -0.3715 0.2549 0.5836 0.049 Uiso 1 1 calc R . . H11A H -0.3917 0.0511 0.6672 0.049 Uiso 1 1 calc R . . H1W H 0.443(6) 0.662(11) 0.699(5) 0.053(17) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.0235(3) 0.0315(4) 0.0375(4) 0.00158(11) 0.0050(2) -0.00049(10) S1 0.0311(5) 0.0321(5) 0.0449(6) 0.0008(3) 0.0077(4) -0.0033(3) O1W 0.031(2) 0.045(2) 0.053(3) 0.000 0.0053(19) 0.000 N12 0.0314(17) 0.0408(18) 0.047(2) 0.0065(17) 0.0085(15) 0.0012(15) C1 0.0297(18) 0.0334(16) 0.040(2) -0.0024(15) 0.0054(15) 0.0011(14) N11 0.0306(18) 0.044(2) 0.048(2) -0.0021(14) 0.0091(16) 0.0024(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C1 1.781(4) . ? S1 S1 2.029(2) 2_556 ? N12 C1 1.317(5) . ? C1 N11 1.311(6) . ? 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 S1 102.93(14) . 2_556 ? N11 C1 N12 123.2(4) . . ? N11 C1 S1 114.3(3) . . ? N12 C1 S1 122.5(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag S1 S1 C1 N11 -176.7(3) 2_556 . . . ? S1 S1 C1 N12 4.0(4) 2_556 . . . ? 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 N12 H12B Br1 0.86 2.46 3.286(4) 161.7 3_566 N12 H12A S1 0.86 2.55 3.070(4) 119.7 2_556 N12 H12A Br1 0.86 2.68 3.390(3) 141.1 . N11 H11B Br1 0.86 2.88 3.606(4) 143.3 3_566 N11 H11B Br1 0.86 2.92 3.392(4) 116.1 1_455 N11 H11A O1W 0.86 2.02 2.868(5) 167.5 1_445 O1W H1W Br1 0.95(5) 2.38(5) 3.326(3) 178(5) . _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 70.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.817 _refine_diff_density_min -1.120 _refine_diff_density_rms 0.141 _database_code_depnum_ccdc_archive 'CCDC 924831' ####################################################################### # # 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_6 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C2 H5 N4 S, I' _chemical_formula_sum 'C2 H5 I N4 S' _chemical_formula_weight 244.06 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' 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 triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 4.5455(2) _cell_length_b 8.6436(3) _cell_length_c 9.5497(3) _cell_angle_alpha 113.700(3) _cell_angle_beta 94.020(3) _cell_angle_gamma 103.347(3) _cell_volume 328.64(2) _cell_formula_units_Z 2 _cell_measurement_temperature 100(1) _cell_measurement_reflns_used 3374 _cell_measurement_theta_min 4.2700 _cell_measurement_theta_max 27.6980 _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.466 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 228 _exptl_absorpt_coefficient_mu 5.092 _exptl_absorpt_correction_T_min 0.55728 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET) (compiled Dec 3 2012,18:21:49) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(1) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_detector_area_resol_mean 16.1544 _diffrn_measurement_method '\w scans' _diffrn_reflns_number 4992 _diffrn_reflns_av_R_equivalents 0.0199 _diffrn_reflns_av_sigmaI/netI 0.0198 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 4.28 _diffrn_reflns_theta_max 28.01 _reflns_number_total 1433 _reflns_number_gt 1362 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_structure_solution ? _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^ > 2\s(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^)+(0.0252P)^2^+0.0930P] 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 1433 _refine_ls_number_parameters 73 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0192 _refine_ls_R_factor_gt 0.0173 _refine_ls_wR_factor_ref 0.0419 _refine_ls_wR_factor_gt 0.0413 _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_restrained_S_all 1.073 _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 I1 I 0.35538(4) 0.10593(2) 0.341132(17) 0.01509(7) Uani 1 1 d . . . S1 S -0.15585(15) 0.52227(9) 0.66265(7) 0.01554(14) Uani 1 1 d . . . N2 N -0.0226(5) 0.3532(3) 0.6592(3) 0.0170(5) Uani 1 1 d . . . H2 H -0.0804 0.2471 0.5816 0.020 Uiso 1 1 calc R . . C3 C 0.1793(6) 0.3986(3) 0.7871(3) 0.0139(5) Uani 1 1 d . . . N31 N 0.3179(5) 0.2880(3) 0.8080(3) 0.0177(5) Uani 1 1 d . . . H31A H 0.2779 0.1794 0.7356 0.021 Uiso 1 1 calc R . . H31B H 0.4497 0.3234 0.8942 0.021 Uiso 1 1 calc R . . N4 N 0.2363(5) 0.5649(3) 0.8957(2) 0.0142(4) Uani 1 1 d . . . C5 C 0.0766(6) 0.6492(4) 0.8457(3) 0.0148(5) Uani 1 1 d . . . N51 N 0.0856(6) 0.8144(3) 0.9262(3) 0.0223(5) Uani 1 1 d . . . H51A H 0.2025 0.8758 1.0189 0.027 Uiso 1 1 calc R . . H51B H -0.0251 0.8639 0.8874 0.027 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 0.01551(10) 0.01309(10) 0.01208(10) 0.00150(7) -0.00240(6) 0.00443(7) S1 0.0178(3) 0.0155(3) 0.0105(3) 0.0027(3) -0.0003(2) 0.0060(3) N2 0.0197(12) 0.0115(11) 0.0133(11) -0.0007(9) -0.0027(9) 0.0052(9) C3 0.0136(12) 0.0141(13) 0.0123(12) 0.0046(10) 0.0027(9) 0.0026(10) N31 0.0216(12) 0.0110(12) 0.0148(11) 0.0005(9) -0.0031(9) 0.0055(9) N4 0.0165(11) 0.0131(11) 0.0106(10) 0.0027(9) -0.0001(8) 0.0051(9) C5 0.0177(13) 0.0165(14) 0.0089(11) 0.0037(10) 0.0023(10) 0.0058(11) N51 0.0345(14) 0.0176(13) 0.0121(11) 0.0013(10) -0.0036(10) 0.0140(11) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 N2 1.696(2) . ? S1 C5 1.744(3) . ? N2 C3 1.334(3) . ? N2 H2 0.8800 . ? C3 N31 1.328(3) . ? C3 N4 1.342(3) . ? N31 H31A 0.8800 . ? N31 H31B 0.8800 . ? N4 C5 1.327(3) . ? C5 N51 1.310(4) . ? N51 H51A 0.8800 . ? N51 H51B 0.8800 . ? 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 N2 S1 C5 87.06(12) . . ? C3 N2 S1 112.62(19) . . ? C3 N2 H2 123.7 . . ? S1 N2 H2 123.7 . . ? N31 C3 N2 122.9(2) . . ? N31 C3 N4 121.2(2) . . ? N2 C3 N4 115.9(2) . . ? C3 N31 H31A 120.0 . . ? C3 N31 H31B 120.0 . . ? H31A N31 H31B 120.0 . . ? C5 N4 C3 109.5(2) . . ? N51 C5 N4 123.7(2) . . ? N51 C5 S1 121.4(2) . . ? N4 C5 S1 114.9(2) . . ? C5 N51 H51A 120.0 . . ? C5 N51 H51B 120.0 . . ? H51A N51 H51B 120.0 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 S1 N2 C3 -0.6(2) . . . . ? S1 N2 C3 N31 -178.6(2) . . . . ? S1 N2 C3 N4 1.4(3) . . . . ? N31 C3 N4 C5 178.4(2) . . . . ? N2 C3 N4 C5 -1.6(3) . . . . ? C3 N4 C5 N51 -179.7(2) . . . . ? C3 N4 C5 S1 1.1(3) . . . . ? N2 S1 C5 N51 -179.5(2) . . . . ? N2 S1 C5 N4 -0.3(2) . . . . ? 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 N2 H2 I1 0.88 2.97 3.546(2) 124.8 1_455 N31 H31B N4 0.88 2.10 2.974(3) 173.9 2_667 N31 H31A I1 0.88 3.14 3.697(2) 123.0 2_556 N51 H51B I1 0.88 2.70 3.513(2) 155.1 2_566 N51 H51A I1 0.88 2.84 3.664(2) 157.1 1_566 _diffrn_measured_fraction_theta_max 0.905 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.147 _refine_diff_density_min -0.513 _refine_diff_density_rms 0.112 _database_code_depnum_ccdc_archive 'CCDC 939694' ####################################################################### # # 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_7 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C4 H12 N4 S2), I4, 2(Br)' _chemical_formula_sum 'C8 H24 Br2 I4 N8 S4' _chemical_formula_weight 1028.03 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' 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Cmca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y+1/2, z+1/2' 'x, -y, -z' '-x+1/2, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, -y+1, z+1/2' 'x+1/2, -y+1/2, -z' '-x+1, y+1/2, -z+1/2' '-x, -y, -z' 'x, y-1/2, -z-1/2' '-x, y, z' 'x-1/2, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, y, -z-1/2' '-x+1/2, y+1/2, z' 'x, -y+1/2, z-1/2' _cell_length_a 11.3150(13) _cell_length_b 11.134(2) _cell_length_c 21.9321(15) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2763.0(7) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 2065 _cell_measurement_theta_min 3.1400 _cell_measurement_theta_max 28.9209 _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.471 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1896 _exptl_absorpt_coefficient_mu 7.718 _exptl_absorpt_correction_T_min 0.60938 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(2) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_detector_area_resol_mean 16.1544 _diffrn_reflns_number 8716 _diffrn_reflns_av_R_equivalents 0.0495 _diffrn_reflns_av_sigmaI/netI 0.0432 _diffrn_measurement_method '\w scans' _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 3.17 _diffrn_reflns_theta_max 29.22 _reflns_number_total 1799 _reflns_number_gt 1345 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_structure_solution ? _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^ > 2\s(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^)+(0.0620P)^2^+17.3681P] 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 1799 _refine_ls_number_parameters 65 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0743 _refine_ls_R_factor_gt 0.0488 _refine_ls_wR_factor_ref 0.1311 _refine_ls_wR_factor_gt 0.1199 _refine_ls_goodness_of_fit_ref 1.087 _refine_ls_restrained_S_all 1.087 _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 I1 I 0.0000 0.05776(7) 0.05600(4) 0.0476(3) Uani 1 2 d S . . I2 I 0.0000 0.20672(7) 0.19145(3) 0.0440(2) Uani 1 2 d S . . Br1 Br 0.5000 0.14203(8) 0.08298(5) 0.0354(3) Uani 1 2 d S . . S1 S 0.18981(18) 0.51854(17) 0.21626(8) 0.0405(5) Uani 1 1 d . . . N11 N 0.3344(7) 0.3413(6) 0.1768(3) 0.0459(16) Uani 1 1 d . . . H11A H 0.3597 0.2923 0.1495 0.055 Uiso 1 1 calc R . . H11B H 0.3641 0.3399 0.2129 0.055 Uiso 1 1 calc R . . N12 N 0.2028(6) 0.4242(6) 0.1102(3) 0.0456(16) Uani 1 1 d . . . H12 H 0.1554 0.4830 0.1032 0.055 Uiso 1 1 calc R . . C1 C 0.2513(7) 0.4175(6) 0.1636(3) 0.0357(15) Uani 1 1 d . . . C12 C 0.2236(10) 0.3387(8) 0.0614(4) 0.060(2) Uani 1 1 d . . . H12A H 0.3034 0.3468 0.0470 0.089 Uiso 1 1 calc R . . H12B H 0.1697 0.3541 0.0285 0.089 Uiso 1 1 calc R . . H12C H 0.2116 0.2586 0.0764 0.089 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 0.0493(5) 0.0451(4) 0.0483(5) 0.0054(3) 0.000 0.000 I2 0.0483(5) 0.0468(4) 0.0368(4) 0.0016(3) 0.000 0.000 Br1 0.0360(6) 0.0310(5) 0.0391(6) -0.0019(4) 0.000 0.000 S1 0.0525(12) 0.0383(9) 0.0306(9) -0.0010(7) -0.0029(8) 0.0054(8) N11 0.055(4) 0.051(4) 0.032(3) -0.010(3) 0.001(3) 0.007(3) N12 0.050(4) 0.053(4) 0.035(3) 0.002(3) -0.001(3) -0.003(3) C1 0.044(4) 0.036(3) 0.028(3) 0.004(3) 0.002(3) -0.009(3) C12 0.072(7) 0.073(6) 0.035(4) -0.014(4) -0.002(4) -0.012(5) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 I1 2.7728(16) 9 ? I1 I2 3.4022(11) . ? S1 C1 1.756(7) . ? S1 S1 2.011(4) 4 ? N11 C1 1.299(10) . ? N12 C1 1.296(10) . ? N12 C12 1.452(10) . ? 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 I1 I1 I2 178.46(4) 9 . ? C1 S1 S1 102.4(3) . 4 ? C1 N12 C12 124.1(7) . . ? N12 C1 N11 123.1(7) . . ? N12 C1 S1 112.9(6) . . ? N11 C1 S1 124.0(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 N11 H11A Br1 0.86 2.73 3.559(7) 162.8 . N11 H11B I2 0.86 2.99 3.756(7) 148.7 14_556 N12 H12 Br1 0.86 2.53 3.392(7) 174.6 5_455 _diffrn_measured_fraction_theta_max 0.916 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.959 _refine_diff_density_min -1.066 _refine_diff_density_rms 0.185 _database_code_depnum_ccdc_archive 'CCDC 939695' ####################################################################### # # 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_8 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C5 H11 I N2 O S' _chemical_formula_weight 274.12 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 ' triclinic' _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.0530(4) _cell_length_b 8.5003(5) _cell_length_c 8.6957(5) _cell_angle_alpha 114.890(5) _cell_angle_beta 91.954(5) _cell_angle_gamma 99.007(5) _cell_volume 464.16(5) _cell_formula_units_Z 2 _cell_measurement_temperature 100(1) _cell_measurement_reflns_used 1846 _cell_measurement_theta_min 3.5866 _cell_measurement_theta_max 27.9389 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.961 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 264 _exptl_absorpt_coefficient_mu 3.619 _exptl_absorpt_correction_T_min 0.40536 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(1) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_detector_area_resol_mean 16.1544 _diffrn_measurement_method '\w scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3173 _diffrn_reflns_av_R_equivalents 0.0194 _diffrn_reflns_av_sigmaI/netI 0.0242 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.59 _diffrn_reflns_theta_max 28.00 _reflns_number_total 1893 _reflns_number_gt 1814 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_structure_solution ? _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^)+(0.0315P)^2^+0.8957P] 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 1893 _refine_ls_number_parameters 96 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0244 _refine_ls_R_factor_gt 0.0229 _refine_ls_wR_factor_ref 0.0610 _refine_ls_wR_factor_gt 0.0604 _refine_ls_goodness_of_fit_ref 1.081 _refine_ls_restrained_S_all 1.081 _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 1.35346(3) 0.18845(3) 0.83684(3) 0.01749(9) Uani 1 1 d . . . S1 S 0.77389(12) 0.23210(10) 0.61593(10) 0.01335(17) Uani 1 1 d . . . O1W O 1.6267(4) -0.1450(3) 0.7741(3) 0.0226(6) Uani 1 1 d . . . C2 C 0.9923(5) 0.2597(4) 0.5369(4) 0.0120(6) Uani 1 1 d . . . N21 N 1.0453(4) 0.1379(4) 0.3994(4) 0.0155(6) Uani 1 1 d . . . H21A H 1.1562 0.1586 0.3663 0.019 Uiso 1 1 calc R . . H21B H 0.9689 0.0381 0.3430 0.019 Uiso 1 1 calc R . . C31 C 1.2970(5) 0.4673(4) 0.5937(4) 0.0171(7) Uani 1 1 d . . . H31A H 1.3774 0.3916 0.6071 0.026 Uiso 1 1 calc R . . H31B H 1.3501 0.5878 0.6703 0.026 Uiso 1 1 calc R . . H31C H 1.2914 0.4540 0.4784 0.026 Uiso 1 1 calc R . . N3 N 1.1014(4) 0.4189(3) 0.6327(3) 0.0122(5) Uani 1 1 d . . . C4 C 1.0150(5) 0.5249(4) 0.7740(4) 0.0135(6) Uani 1 1 d . . . C5 C 0.8385(5) 0.4435(4) 0.7812(4) 0.0144(6) Uani 1 1 d . . . H5 H 0.7599 0.4899 0.8687 0.016(10) Uiso 1 1 d R . . C41 C 1.1201(5) 0.7046(4) 0.8949(4) 0.0178(7) Uani 1 1 d . . . H41A H 1.0450 0.7552 0.9873 0.027 Uiso 1 1 calc R . . H41B H 1.1404 0.7783 0.8361 0.027 Uiso 1 1 calc R . . H41C H 1.2426 0.6957 0.9390 0.027 Uiso 1 1 calc R . . H1WA H 1.5623 -0.0878 0.7840 0.016(12) Uiso 1 1 d R . . H1WB H 1.6421 -0.1465 0.8616 0.025(12) Uiso 1 1 d 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 0.01462(13) 0.01816(13) 0.01847(13) 0.00758(9) 0.00172(8) 0.00068(8) S1 0.0108(4) 0.0121(4) 0.0168(4) 0.0064(3) 0.0027(3) 0.0003(3) O1W 0.0248(14) 0.0220(13) 0.0219(14) 0.0092(11) 0.0097(11) 0.0066(11) C2 0.0102(15) 0.0149(15) 0.0162(16) 0.0116(13) 0.0018(12) 0.0025(12) N21 0.0138(14) 0.0142(13) 0.0178(14) 0.0067(11) 0.0043(11) 0.0004(11) C31 0.0145(17) 0.0169(16) 0.0220(18) 0.0115(14) 0.0042(14) -0.0008(13) N3 0.0105(13) 0.0130(13) 0.0155(13) 0.0087(11) 0.0013(11) 0.0015(10) C4 0.0141(16) 0.0130(15) 0.0144(16) 0.0072(13) -0.0014(13) 0.0022(12) C5 0.0156(16) 0.0140(15) 0.0133(15) 0.0056(12) 0.0018(12) 0.0033(12) C41 0.0180(17) 0.0139(16) 0.0170(16) 0.0042(13) -0.0019(13) -0.0010(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 S1 C2 1.731(3) . ? S1 C5 1.740(3) . ? O1W H1WA 0.6969 . ? O1W H1WB 0.7709 . ? C2 N21 1.323(4) . ? C2 N3 1.341(4) . ? N21 H21A 0.8600 . ? N21 H21B 0.8600 . ? C31 N3 1.469(4) . ? C31 H31A 0.9600 . ? C31 H31B 0.9600 . ? C31 H31C 0.9600 . ? N3 C4 1.409(4) . ? C4 C5 1.343(5) . ? C4 C41 1.493(4) . ? C5 H5 0.9414 . ? C41 H41A 0.9600 . ? C41 H41B 0.9600 . ? C41 H41C 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 C2 S1 C5 90.02(16) . . ? H1WA O1W H1WB 105.5 . . ? N21 C2 N3 124.3(3) . . ? N21 C2 S1 124.0(3) . . ? N3 C2 S1 111.7(2) . . ? C2 N21 H21A 120.0 . . ? C2 N21 H21B 120.0 . . ? H21A N21 H21B 120.0 . . ? N3 C31 H31A 109.5 . . ? N3 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? N3 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C2 N3 C4 113.9(3) . . ? C2 N3 C31 120.9(3) . . ? C4 N3 C31 125.2(3) . . ? C5 C4 N3 112.0(3) . . ? C5 C4 C41 127.7(3) . . ? N3 C4 C41 120.2(3) . . ? C4 C5 S1 112.4(3) . . ? C4 C5 H5 125.1 . . ? S1 C5 H5 122.4 . . ? C4 C41 H41A 109.5 . . ? C4 C41 H41B 109.5 . . ? H41A C41 H41B 109.5 . . ? C4 C41 H41C 109.5 . . ? H41A C41 H41C 109.5 . . ? H41B C41 H41C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 S1 C2 N21 179.6(3) . . . . ? C5 S1 C2 N3 0.1(2) . . . . ? N21 C2 N3 C4 -179.2(3) . . . . ? S1 C2 N3 C4 0.4(3) . . . . ? N21 C2 N3 C31 -2.6(5) . . . . ? S1 C2 N3 C31 177.0(2) . . . . ? C2 N3 C4 C5 -0.8(4) . . . . ? C31 N3 C4 C5 -177.2(3) . . . . ? C2 N3 C4 C41 178.8(3) . . . . ? C31 N3 C4 C41 2.4(5) . . . . ? N3 C4 C5 S1 0.8(4) . . . . ? C41 C4 C5 S1 -178.7(3) . . . . ? C2 S1 C5 C4 -0.6(3) . . . . ? 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 O1W H1WA I1 0.70 2.85 3.539(3) 170.8 . O1W H1WB I1 0.77 2.79 3.555(3) 171.5 2_857 N21 H21B I1 0.86 2.68 3.492(3) 158.2 2_756 N21 H21A O1W 0.86 1.98 2.811(4) 162.6 2_856 _diffrn_measured_fraction_theta_max 0.841 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.771 _refine_diff_density_min -0.550 _refine_diff_density_rms 0.119 _database_code_depnum_ccdc_archive 'CCDC 924832' ####################################################################### # # 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_9 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C4 H9 N4 S, I3' _chemical_formula_sum 'C4 H9 I3 N4 S' _chemical_formula_weight 525.91 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' 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' N N 0.0061 0.0033 '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 bca' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 12.6402(4) _cell_length_b 13.7770(8) _cell_length_c 14.1348(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2461.49(18) _cell_formula_units_Z 8 _cell_measurement_temperature 100.00(10) _cell_measurement_reflns_used 1530 _cell_measurement_theta_min 3.2168 _cell_measurement_theta_max 28.0642 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.838 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1888 _exptl_absorpt_coefficient_mu 7.752 _exptl_absorpt_correction_T_min 0.85201 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100.00(10) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_detector_area_resol_mean 16.1544 _diffrn_measurement_method '\w scans' _diffrn_reflns_number 6414 _diffrn_reflns_av_R_equivalents 0.0427 _diffrn_reflns_av_sigmaI/netI 0.0610 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.22 _diffrn_reflns_theta_max 28.13 _reflns_number_total 2547 _reflns_number_gt 1990 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_structure_solution ? _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^)+(0.0201P)^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_number_reflns 2547 _refine_ls_number_parameters 111 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0564 _refine_ls_R_factor_gt 0.0367 _refine_ls_wR_factor_ref 0.0716 _refine_ls_wR_factor_gt 0.0635 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.040 _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 I2 I 0.60116(3) -0.08609(3) 0.41970(3) 0.01740(13) Uani 1 1 d . . . I1 I 0.82430(3) -0.02707(3) 0.45254(3) 0.01924(14) Uani 1 1 d . . . I3 I 0.39001(4) -0.15377(4) 0.38434(4) 0.02171(14) Uani 1 1 d . . . S1 S 0.54156(13) 0.06028(13) 0.18318(14) 0.0195(4) Uani 1 1 d . . . N4 N 0.6452(4) 0.1622(4) 0.2966(4) 0.0146(13) Uani 1 1 d . . . N51 N 0.7546(4) 0.0675(4) 0.1969(4) 0.0211(15) Uani 1 1 d . . . H51B H 0.8114 0.0897 0.2224 0.025 Uiso 1 1 calc R . . H51A H 0.7585 0.0258 0.1518 0.025 Uiso 1 1 calc R . . C3 C 0.5380(5) 0.1830(5) 0.3101(5) 0.0176(16) Uani 1 1 d . . . N2 N 0.4722(4) 0.1314(4) 0.2576(4) 0.0166(14) Uani 1 1 d . . . N31 N 0.5106(4) 0.2506(4) 0.3715(4) 0.0202(15) Uani 1 1 d . . . H31 H 0.5580 0.2750 0.4080 0.024 Uiso 1 1 calc R . . C5 C 0.6601(5) 0.0979(5) 0.2273(5) 0.0144(16) Uani 1 1 d . . . C41 C 0.7293(5) 0.2173(5) 0.3460(5) 0.0191(17) Uani 1 1 d . . . H41A H 0.7966 0.1873 0.3342 0.029 Uiso 1 1 calc R . . H41B H 0.7155 0.2175 0.4127 0.029 Uiso 1 1 calc R . . H41C H 0.7304 0.2829 0.3230 0.029 Uiso 1 1 calc R . . C32 C 0.4018(5) 0.2848(5) 0.3787(5) 0.0246(18) Uani 1 1 d . . . H31A H 0.3808 0.3132 0.3196 0.037 Uiso 1 1 calc R . . H31C H 0.3969 0.3325 0.4279 0.037 Uiso 1 1 calc R . . H31B H 0.3562 0.2311 0.3932 0.037 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 I2 0.0129(2) 0.0215(3) 0.0179(3) -0.0015(2) 0.00119(19) 0.00114(19) I1 0.0130(2) 0.0257(3) 0.0189(3) -0.0014(2) 0.0016(2) -0.00121(19) I3 0.0135(2) 0.0272(3) 0.0244(3) -0.0048(2) -0.0016(2) -0.0001(2) S1 0.0090(8) 0.0292(10) 0.0203(11) -0.0063(9) -0.0015(8) -0.0014(8) N4 0.011(3) 0.022(3) 0.011(3) -0.006(3) -0.004(2) 0.003(2) N51 0.013(3) 0.031(3) 0.019(4) -0.009(3) -0.003(3) -0.002(3) C3 0.011(3) 0.029(4) 0.013(4) 0.009(3) 0.000(3) 0.002(3) N2 0.008(3) 0.022(3) 0.019(4) -0.002(3) -0.002(3) 0.002(2) N31 0.016(3) 0.028(4) 0.017(4) -0.011(3) -0.002(3) -0.001(3) C5 0.011(4) 0.022(4) 0.010(4) 0.001(3) -0.004(3) 0.002(3) C41 0.015(4) 0.023(4) 0.019(4) -0.003(4) -0.006(3) 0.003(3) C32 0.023(4) 0.025(4) 0.025(5) -0.008(4) 0.004(3) -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 I2 I3 2.8710(6) . ? I2 I1 2.9718(6) . ? S1 N2 1.684(6) . ? S1 C5 1.704(7) . ? N4 C5 1.335(8) . ? N4 C3 1.398(8) . ? N4 C41 1.481(8) . ? N51 C5 1.336(8) . ? N51 H51B 0.8600 . ? N51 H51A 0.8600 . ? C3 N31 1.320(8) . ? C3 N2 1.321(8) . ? N31 C32 1.456(8) . ? N31 H31 0.8600 . ? C41 H41A 0.9600 . ? C41 H41B 0.9600 . ? C41 H41C 0.9600 . ? C32 H31A 0.9600 . ? C32 H31C 0.9600 . ? C32 H31B 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 I3 I2 I1 176.70(2) . . ? N2 S1 C5 93.0(3) . . ? C5 N4 C3 111.9(6) . . ? C5 N4 C41 125.8(5) . . ? C3 N4 C41 121.8(6) . . ? C5 N51 H51B 120.0 . . ? C5 N51 H51A 120.0 . . ? H51B N51 H51A 120.0 . . ? N31 C3 N2 125.7(6) . . ? N31 C3 N4 119.2(6) . . ? N2 C3 N4 115.1(6) . . ? C3 N2 S1 109.6(5) . . ? C3 N31 C32 121.5(6) . . ? C3 N31 H31 119.3 . . ? C32 N31 H31 119.3 . . ? N4 C5 N51 124.8(6) . . ? N4 C5 S1 110.3(5) . . ? N51 C5 S1 125.0(6) . . ? N4 C41 H41A 109.5 . . ? N4 C41 H41B 109.5 . . ? H41A C41 H41B 109.5 . . ? N4 C41 H41C 109.5 . . ? H41A C41 H41C 109.5 . . ? H41B C41 H41C 109.5 . . ? N31 C32 H31A 109.5 . . ? N31 C32 H31C 109.5 . . ? H31A C32 H31C 109.5 . . ? N31 C32 H31B 109.5 . . ? H31A C32 H31B 109.5 . . ? H31C C32 H31B 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 N4 C3 N31 -175.1(6) . . . . ? C41 N4 C3 N31 -3.0(9) . . . . ? C5 N4 C3 N2 4.4(8) . . . . ? C41 N4 C3 N2 176.5(6) . . . . ? N31 C3 N2 S1 175.4(6) . . . . ? N4 C3 N2 S1 -4.0(7) . . . . ? C5 S1 N2 C3 2.1(5) . . . . ? N2 C3 N31 C32 -8.3(11) . . . . ? N4 C3 N31 C32 171.1(6) . . . . ? C3 N4 C5 N51 177.4(6) . . . . ? C41 N4 C5 N51 5.7(11) . . . . ? C3 N4 C5 S1 -2.5(7) . . . . ? C41 N4 C5 S1 -174.3(5) . . . . ? N2 S1 C5 N4 0.3(5) . . . . ? N2 S1 C5 N51 -179.7(6) . . . . ? _diffrn_measured_fraction_theta_max 0.846 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.380 _refine_diff_density_min -0.955 _refine_diff_density_rms 0.247 _database_code_depnum_ccdc_archive 'CCDC 924833'