# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2003 data_global _journal_coden_Cambridge 177 loop_ _publ_author_name 'Peter Courtney Junk' 'Marcus L. Cole' 'Chaveng Pakawatchai' 'Brian W. Skelton' 'Yupa Thanyasirikul' 'Allan H. White' _publ_contact_author_name 'Dr Peter Courtney Junk' _publ_contact_author_address ; Chemistry Monash University School of Chemistry Box 23, Monash University Clayton Victoria AUSTRALIA ; _publ_contact_author_email PETER.JUNK@SCI.MONASH.EDU.AU _publ_requested_journal 'Organic & Biomolecular Chemistry' _publ_section_title ; Reappraising the formation of Jaffe's Base: Studies of the treatment of imidazolidine-2-thione with mild oxidising agents ; _publ_section_references ; Hall, S.R., King, G.S.D., and Stewart., J.M. (1995). The Xtal 3.5 User's Manual. University of Western Australia, Lamb: Perth. ; data_jaffe _database_code_CSD 187057 _audit_creation_method Xtal3.6 _audit_creation_date 02-05-07 _audit_update_record ? _chemical_formula_sum 'C6 H10 N4 S1' _chemical_formula_moiety ? _chemical_formula_weight 170.24 _chemical_melting_point ? _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P_1_21/c_1 _symmetry_space_group_name_Hall -p_2ybc loop_ _symmetry_equiv_pos_as_xyz +x,+y,+z -x,1/2+y,1/2-z -x,-y,-z +x,1/2-y,1/2+z _cell_length_a 7.9079(8) _cell_length_b 12.480(2) _cell_length_c 7.7913(7) _cell_angle_alpha 90.00000 _cell_angle_beta 92.890(10) _cell_angle_gamma 90.00000 _cell_volume 767.95(16) _cell_formula_units_Z 4 _exptl_crystal_density_diffrn 1.472 _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength .71073 _cell_measurement_reflns_used 8 _cell_measurement_theta_min 13.5 _cell_measurement_theta_max 14.0 _cell_measurement_temperature 293 _exptl_absorpt_coefficient_mu .357 _exptl_crystal_description block _exptl_crystal_size_max .59 _exptl_crystal_size_mid .58 _exptl_crystal_size_min .37 _exptl_crystal_size_rad ? _exptl_crystal_colour colourless _diffrn_measurement_device_type ; CAD4 diffractometer ; _diffrn_measurement_method '2\q-\w scans' _diffrn_detector_area_resol_mean ? _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _diffrn_reflns_number 1249 _reflns_number_total 1249 _reflns_Friedel_coverage 0 _reflns_number_gt 763 _reflns_threshold_expression 'I > 2.00 sig(I )' _diffrn_reflns_theta_max 24.96 _diffrn_reflns_theta_full ? _diffrn_measured_fraction_theta_max ? _diffrn_measured_fraction_theta_full ? _diffrn_reflns_av_R_equivalents ? _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_standards_number 8 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 0 _refine_ls_structure_factor_coef F _refine_ls_R_factor_gt .049 _refine_ls_wR_factor_ref .052 _refine_ls_goodness_of_fit_ref 1.327 _refine_ls_number_reflns 762 _refine_ls_number_parameters 140 _refine_ls_weighting_scheme sigma _refine_ls_weighting_details ? _refine_ls_hydrogen_treatment refall _refine_ls_shift/su_max .0005 _refine_diff_density_min -.227 _refine_diff_density_max .233 _refine_ls_extinction_method ? _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? # 3. Information for the "methods" section #----------------------------------------- _computing_data_collection 'Enraf Nonius Software' _computing_cell_refinement 'Enraf Nonius Software' _computing_data_reduction 'xtal DIFDAT SORTRF ADDREF' _computing_structure_solution xtal _computing_structure_refinement 'xtal CRYLSQ' _computing_molecular_graphics xtal _computing_publication_material 'xtal BONDLA CIFIO' # 4. Supplementary data for validation and tables #------------------------------------------------ loop_ _atom_type_symbol _atom_type_description _atom_type_oxidation_number _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C ? 0 24 .002 .002 'Int Tables Vol IV Tables 2.2B and 2.3.1' H ? 0 40 0 0 'Int Tables Vol IV Tables 2.2B and 2.3.1' N ? 0 16 .004 .003 'Int Tables Vol IV Tables 2.2B and 2.3.1' S ? 0 4 .11 .124 'Int Tables Vol IV Tables 2.2B and 2.3.1' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_calc_attached_atom _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group N1 .3921(4) .3582(3) .1852(5) .044(2) Uani ? ? 1.00000 ? ? C2 .3929(6) .4688(3) .2009(6) .045(3) Uani ? ? 1.00000 ? ? S2 .23817(17) .55384(9) .1440(2) .0652(9) Uani ? ? 1.00000 ? ? N3 .5392(5) .4966(3) .2739(6) .056(3) Uani ? ? 1.00000 ? ? C4 .6524(7) .4092(4) .3162(9) .056(4) Uani ? ? 1.00000 ? ? C5 .5529(6) .3126(4) .2511(9) .053(3) Uani ? ? 1.00000 ? ? N1' .2886(4) .1893(3) .1238(5) .051(2) Uani ? ? 1.00000 ? ? C2' .2643(5) .2908(3) .1275(6) .042(3) Uani ? ? 1.00000 ? ? N3' .1089(6) .3253(3) .0777(7) .070(3) Uani ? ? 1.00000 ? ? C4' .0100(7) .2376(4) .0136(10) .061(4) Uani ? ? 1.00000 ? ? C5' .1237(7) .1434(4) .0624(9) .054(3) Uani ? ? 1.00000 ? ? H3 .566(6) .554(4) .286(6) .048(14) Uiso ? ? 1.00000 ? ? H41 .749(6) .413(3) .262(6) .056(16) Uiso ? ? 1.00000 ? ? H42 .669(6) .405(4) .444(7) .083(19) Uiso ? ? 1.00000 ? ? H51 .604(7) .276(4) .164(7) .09(2) Uiso ? ? 1.00000 ? ? H52 .535(5) .269(4) .344(6) .056(15) Uiso ? ? 1.00000 ? ? H3' .085(6) .381(3) .063(6) .051(17) Uiso ? ? 1.00000 ? ? H41' -.095(6) .234(4) .065(6) .073(18) Uiso ? ? 1.00000 ? ? H42' -.000(6) .241(4) -.105(6) .071(18) Uiso ? ? 1.00000 ? ? H51' .087(5) .102(4) .149(6) .051(15) Uiso ? ? 1.00000 ? ? H52' .153(6) .098(4) -.025(7) .082(19) Uiso ? ? 1.00000 ? ? loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 N1 .034(2) .032(2) .067(3) .0033(16) -.003(2) -.0028(18) C2 .048(3) .035(3) .050(3) .000(2) .001(2) .001(2) S2 .0577(9) .0388(7) .0975(12) .0100(6) -.0120(7) .0024(8) N3 .049(3) .033(3) .085(4) -.006(2) -.012(2) -.004(2) C4 .041(3) .046(3) .081(5) .008(3) -.011(3) -.006(3) C5 .048(3) .039(3) .071(4) .007(3) -.010(3) .001(3) N1' .048(2) .033(2) .071(3) .0002(18) -.004(2) -.003(2) C2' .038(3) .043(2) .044(3) -.000(2) .001(2) .003(2) N3' .047(3) .039(3) .120(4) .003(2) -.031(2) -.005(3) C4' .053(4) .052(3) .078(5) -.001(3) -.012(4) -.003(3) C5' .053(4) .041(3) .068(4) -.007(3) -.000(3) -.003(3) # 5. Molecular Geometry #---------------------- loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag #<< enter YES for value to be published N1 C2 . . 1.386(5) ? N1 C5 . . 1.462(6) ? N1 C2' . . 1.373(5) ? C2 S2 . . 1.663(5) ? C2 N3 . . 1.310(6) ? N3 C4 . . 1.439(7) ? N3 H3 . . .75(4) ? C4 C5 . . 1.513(7) ? C4 H41 . . .89(5) ? C4 H42 . . 1.00(5) ? C5 H51 . . .93(6) ? C5 H52 . . .92(5) ? N1' C2' . . 1.282(6) ? N1' C5' . . 1.481(6) ? C2' N3' . . 1.342(6) ? N3' C4' . . 1.422(7) ? N3' H3' . . .73(4) ? C4' C5' . . 1.516(8) ? C4' H41' . . .95(5) ? C4' H42' . . .92(5) ? C5' H51' . . .91(4) ? C5' H52' . . .92(5) ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag #<< enter YES for value to be published C2 N1 C5 . . . 110.9(3) ? C2 N1 C2' . . . 129.7(4) ? C5 N1 C2' . . . 119.3(3) ? N1 C2 S2 . . . 127.8(3) ? N1 C2 N3 . . . 107.6(4) ? S2 C2 N3 . . . 124.7(3) ? C2 N3 C4 . . . 115.1(4) ? C2 N3 H3 . . . 123(3) ? C4 N3 H3 . . . 122(3) ? N3 C4 C5 . . . 102.7(4) ? N3 C4 H41 . . . 113(3) ? N3 C4 H42 . . . 108(3) ? C5 C4 H41 . . . 109(3) ? C5 C4 H42 . . . 109(3) ? H41 C4 H42 . . . 114(4) ? N1 C5 C4 . . . 103.7(4) ? N1 C5 H51 . . . 110(3) ? N1 C5 H52 . . . 110(3) ? C4 C5 H51 . . . 114(3) ? C4 C5 H52 . . . 107(3) ? H51 C5 H52 . . . 112(4) ? C2' N1' C5' . . . 105.0(4) ? N1 C2' N1' . . . 120.3(4) ? N1 C2' N3' . . . 123.1(4) ? N1' C2' N3' . . . 116.6(4) ? C2' N3' C4' . . . 109.5(4) ? C2' N3' H3' . . . 125(4) ? C4' N3' H3' . . . 123(4) ? N3' C4' C5' . . . 101.6(5) ? N3' C4' H41' . . . 112(3) ? N3' C4' H42' . . . 110(3) ? C5' C4' H41' . . . 112(3) ? C5' C4' H42' . . . 108(3) ? H41' C4' H42' . . . 113(4) ? N1' C5' C4' . . . 106.5(4) ? N1' C5' H51' . . . 107(3) ? N1' C5' H52' . . . 103(3) ? C4' C5' H51' . . . 115(3) ? C4' C5' H52' . . . 117(3) ? H51' C5' H52' . . . 107(4) ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag #<< enter YES for value to be published ? ? ? ? ? ? ? ? ? ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_D _geom_hbond_site_symmetry_H _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag #<< enter YES for value to be published ? ? ? ? ? ? ? ? ? ? ? #-------------------------------------------------------------------------- # Special items requested by author for inclusion in paper #-------------------------------------------------------------------------- loop_ _publ_manuscript_incl_extra_item _publ_manuscript_incl_extra_defn ? ? #-------------------------------------------------------------------------- # Items which are non-mandatory for Acta C submissions #-------------------------------------------------------------------------- _atom_sites_solution_primary ? _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens ? _geom_special_details ? _cell_special_details ; ? ; _exptl_special_details ; ? ; _diffrn_special_details ; ? ; _chemical_compound_source ? _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_analytical ? _chemical_formula_structural ? _exptl_crystal_F_000 360 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 3 5 3 3 -5 3 -3 5 -3 -3 -5 -3 3 6 -2 -3 6 2 -3 -6 2 3 -6 -2 loop_ _diffrn_attenuator_code _diffrn_attenuator_scale ? ? _reflns_limit_h_min 0 _reflns_limit_h_max 8 _reflns_limit_k_min 0 _reflns_limit_k_max 14 _reflns_limit_l_min -9 _reflns_limit_l_max 9 _reflns_number_observed ? _reflns_d_resolution_high .842 _reflns_d_resolution_low 7.898 _diffrn_reflns_av_sigmaI/netI 0 _diffrn_reflns_theta_min 2.58 _diffrn_reflns_reduction_process 'equatorial monochr Lp' _diffrn_ambient_temperature 293 _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector 'scintillation counter' _refine_ls_extinction_expression ? _refine_ls_matrix_type full _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_all .099 _refine_ls_wR_factor_all .062 _refine_ls_goodness_of_fit_all 1.181 _refine_ls_shift/su_mean .00005 #========================================================================== # Structure Factor lists should be submitted as separate files #========================================================================== #data_<structure> # but for xtal use the refln data is needed in same block loop_ _refln_index_h _refln_index_k _refln_index_l _refln_F_meas _refln_F_calc _refln_F_sigma _refln_F_squared_meas _refln_F_squared_calc _refln_F_squared_sigma _refln_observed_status _refln_F_meas_friedel _refln_F_sigma_friedel _refln_F_squared_meas_friedel _refln_F_squared_sigma_friedel ? ? ? ? ? ? ? ? ? ? ? ? ? ? #===END data_etucub _database_code_CSD 187058 _audit_creation_method Xtal3.6 _audit_creation_date 02-05-08 _audit_update_record ? # 2. EXPERIMENTAL DATA #--------------------- _chemical_formula_sum 'C6 H11 Br1 N4 S1' _chemical_formula_moiety ? _chemical_formula_weight 251.15 _chemical_melting_point ? _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P_n_m_a _symmetry_space_group_name_Hall -p_2ac_2n loop_ _symmetry_equiv_pos_as_xyz +x,+y,+z 1/2-x,-y,1/2+z 1/2+x,1/2-y,1/2-z -x,1/2+y,-z -x,-y,-z 1/2+x,+y,1/2-z 1/2-x,1/2+y,1/2+z +x,1/2-y,+z _cell_length_a 15.295(3) _cell_length_b 6.895(7) _cell_length_c 9.063(2) _cell_angle_alpha 90.00000 _cell_angle_beta 90.00000 _cell_angle_gamma 90.00000 _cell_volume 955.8(10) _cell_formula_units_Z 4 _exptl_crystal_density_diffrn 1.745 _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength .71073 _cell_measurement_reflns_used 6 _cell_measurement_theta_min 24.3 _cell_measurement_theta_max 28.0 _cell_measurement_temperature 293 _exptl_absorpt_coefficient_mu 4.472 _exptl_crystal_description block _exptl_crystal_size_max .59 _exptl_crystal_size_mid .58 _exptl_crystal_size_min .37 _exptl_crystal_size_rad ? _exptl_crystal_colour colourless _diffrn_measurement_device_type ; CAD4 diffractometer ; _diffrn_measurement_method '2\q-\w scans' _diffrn_detector_area_resol_mean ? _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; XTAl absorb ; _exptl_absorpt_correction_T_min .16 _exptl_absorpt_correction_T_max .36 _diffrn_reflns_number 1521 _reflns_number_total 1521 _reflns_Friedel_coverage 0 _reflns_number_gt 1056 _reflns_threshold_expression 'I > 3.00 sig(I )' _diffrn_reflns_theta_max 32.44 _diffrn_reflns_theta_full ? _diffrn_measured_fraction_theta_max ? _diffrn_measured_fraction_theta_full ? _diffrn_reflns_av_R_equivalents ? _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 13 _diffrn_standards_number 6 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 0 _refine_ls_structure_factor_coef F _refine_ls_R_factor_gt .033 _refine_ls_wR_factor_ref .049 _refine_ls_goodness_of_fit_ref 1.148 _refine_ls_number_reflns 1039 _refine_ls_number_parameters 98 _refine_ls_weighting_scheme calc _refine_ls_weighting_details ? _refine_ls_hydrogen_treatment refall _refine_ls_shift/su_max .043 _refine_diff_density_min -.388 _refine_diff_density_max .656 _refine_ls_extinction_method ? _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? # 3. Information for the "methods" section #----------------------------------------- _computing_data_collection 'Enraf Nonius software' _computing_cell_refinement 'Enraf Nonius software' _computing_data_reduction 'xtal ADDREF SORTRF' _computing_structure_solution xtal _computing_structure_refinement 'xtal CRYLSQ' _computing_molecular_graphics xtal _computing_publication_material 'xtal BONDLA CIFIO' # 4. Supplementary data for validation and tables #------------------------------------------------ loop_ _atom_type_symbol _atom_type_description _atom_type_oxidation_number _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C ? 0 24 .002 .002 'Int Tables Vol IV Tables 2.2B and 2.3.1' H ? 0 44 0 0 'Int Tables Vol IV Tables 2.2B and 2.3.1' Br ? 0 4 -.374 2.456 'Int Tables Vol IV Tables 2.2B and 2.3.1' N ? 0 16 .004 .003 'Int Tables Vol IV Tables 2.2B and 2.3.1' S ? 0 4 .11 .124 'Int Tables Vol IV Tables 2.2B and 2.3.1' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_calc_attached_atom _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Br .30184(3) .75000 .49688(4) .0480(3) Uani ? ? 1.00000 ? ? N1 .4454(2) .75000 -.0560(4) .0390(17) Uani ? ? 1.00000 ? ? C2 .4600(3) .75000 .0981(5) .040(2) Uani ? ? 1.00000 ? ? S2 .55497(9) .75000 .18446(12) .0536(7) Uani ? ? 1.00000 ? ? N3 .3810(3) .75000 .1603(4) .050(2) Uani ? ? 1.00000 ? ? C4 .3072(3) .75000 .0590(6) .050(3) Uani ? ? 1.00000 ? ? C5 .3510(3) .75000 -.0910(5) .047(3) Uani ? ? 1.00000 ? ? N1' .4844(2) .75000 -.3044(4) .046(2) Uani ? ? 1.00000 ? ? C2' .5068(3) .75000 -.1634(4) .037(2) Uani ? ? 1.00000 ? ? N3' .5914(2) .75000 -.1454(4) .048(2) Uani ? ? 1.00000 ? ? C4' .6363(3) .75000 -.2875(5) .046(3) Uani ? ? 1.00000 ? ? C5' .5621(3) .75000 -.3969(5) .060(3) Uani ? ? 1.00000 ? ? H3 .348(6) .75000 .273(10) .15(3) Uiso ? ? 1.00000 ? ? H4 .274(3) .871(6) .070(5) .084(12) Uiso ? ? 1.00000 ? ? H5 .337(2) .863(5) -.144(3) .046(9) Uiso ? ? 1.00000 ? ? H1' .437(3) .75000 -.328(5) .038(12) Uiso ? ? 1.00000 ? ? H3' .610(4) .75000 -.073(8) .07(2) Uiso ? ? 1.00000 ? ? H4' .668(2) .856(4) -.298(3) .038(7) Uiso ? ? 1.00000 ? ? H5' .564(3) .862(7) -.457(5) .075(12) Uiso ? ? 1.00000 ? ? loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Br .0376(2) .0732(4) .0333(2) .00000 .00482(15) .00000 N1 .0365(15) .051(2) .0292(14) .00000 .0006(13) .00000 C2 .049(2) .040(2) .0298(17) .00000 .0010(16) .00000 S2 .0569(6) .0702(9) .0335(5) .00000 -.0088(5) .00000 N3 .052(2) .063(3) .0357(17) .00000 .0115(16) .00000 C4 .048(3) .054(4) .047(3) .00000 .012(2) .00000 C5 .037(2) .063(3) .041(2) .00000 .0030(17) .00000 N1' .0372(18) .072(3) .0306(16) .00000 -.0022(14) .00000 C2' .0385(18) .042(2) .0292(16) .00000 .0012(15) .00000 N3' .0365(17) .077(3) .0297(16) .00000 .0020(14) .00000 C4' .041(2) .059(3) .040(2) .00000 .0033(17) .00000 C5' .050(3) .099(5) .030(2) .00000 .005(2) .00000 # 5. Molecular Geometry #---------------------- loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag #<< enter YES for value to be published N1 C2 . . 1.415(5) ? N1 C5 . . 1.478(6) ? N1 C2' . . 1.353(5) ? C2 S2 . . 1.650(4) ? C2 N3 . . 1.332(6) ? N3 C4 . . 1.455(6) ? N3 H3 . . 1.15(9) ? C4 C5 . . 1.516(7) ? C4 H4 . . .98(4) ? C4 H4 . '8 565' .98(4) ? C5 H5 . . .94(3) ? C5 H5 . '8 565' .94(3) ? N1' C2' . . 1.323(5) ? N1' C5' . . 1.454(6) ? N1' H1' . . .75(5) ? C2' N3' . . 1.305(6) ? N3' C4' . . 1.459(6) ? N3' H3' . . .72(7) ? C4' C5' . . 1.507(7) ? C4' H4' . . .88(3) ? C4' H4' . '8 565' .88(3) ? C5' H5' . . .95(5) ? C5' H5' . '8 565' .95(5) ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag #<< enter YES for value to be published C2 N1 C5 . . . 111.5(3) ? C2 N1 C2' . . . 127.0(3) ? C5 N1 C2' . . . 121.6(3) ? N1 C2 S2 . . . 127.4(3) ? N1 C2 N3 . . . 105.9(3) ? S2 C2 N3 . . . 126.7(3) ? C2 N3 C4 . . . 115.9(4) ? C2 N3 H3 . . . 141(4) ? C4 N3 H3 . . . 103(4) ? N3 C4 C5 . . . 102.9(4) ? N3 C4 H4 . . . 110(3) ? N3 C4 H4 . . '8 565' 110(3) ? C5 C4 H4 . . . 109(3) ? C5 C4 H4 . . '8 565' 109(3) ? H4 C4 H4 . . '8 565' 116(4) ? N1 C5 C4 . . . 103.8(4) ? N1 C5 H5 . . . 109(2) ? N1 C5 H5 . . '8 565' 109(2) ? C4 C5 H5 . . . 111(2) ? C4 C5 H5 . . '8 565' 111(2) ? H5 C5 H5 . . '8 565' 112(3) ? C2' N1' C5' . . . 110.2(4) ? C2' N1' H1' . . . 121(3) ? C5' N1' H1' . . . 129(3) ? N1 C2' N1' . . . 121.0(4) ? N1 C2' N3' . . . 126.8(4) ? N1' C2' N3' . . . 112.2(4) ? C2' N3' C4' . . . 110.9(4) ? C2' N3' H3' . . . 121(5) ? C4' N3' H3' . . . 129(5) ? N3' C4' C5' . . . 103.1(4) ? N3' C4' H4' . . . 110.7(19) ? N3' C4' H4' . . '8 565' 110.7(19) ? C5' C4' H4' . . . 109.8(19) ? C5' C4' H4' . . '8 565' 109.8(19) ? H4' C4' H4' . . '8 565' 112(3) ? N1' C5' C4' . . . 103.7(4) ? N1' C5' H5' . . . 111(3) ? N1' C5' H5' . . '8 565' 111(3) ? C4' C5' H5' . . . 111(3) ? C4' C5' H5' . . '8 565' 111(3) ? H5' C5' H5' . . '8 565' 110(4) ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag #<< enter YES for value to be published ? ? ? ? ? ? ? ? ? ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_D _geom_hbond_site_symmetry_H _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag #<< enter YES for value to be published ? ? ? ? ? ? ? ? ? ? ? #-------------------------------------------------------------------------- # Special items requested by author for inclusion in paper #-------------------------------------------------------------------------- loop_ _publ_manuscript_incl_extra_item _publ_manuscript_incl_extra_defn ? ? #-------------------------------------------------------------------------- # Items which are non-mandatory for Acta C submissions #-------------------------------------------------------------------------- _atom_sites_solution_primary ? _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens ? _geom_special_details ? _cell_special_details ; ? ; _exptl_special_details ; ? ; _diffrn_special_details ; ? ; _chemical_compound_source ? _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_analytical ? _chemical_formula_structural ? _exptl_crystal_F_000 504 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? loop_ _diffrn_attenuator_code _diffrn_attenuator_scale ? ? _reflns_limit_h_min 0 _reflns_limit_h_max 23 _reflns_limit_k_min 0 _reflns_limit_k_max 6 _reflns_limit_l_min 0 _reflns_limit_l_max 13 _reflns_number_observed ? _reflns_d_resolution_high .663 _reflns_d_resolution_low 7.785 _diffrn_reflns_av_sigmaI/netI .046 _diffrn_reflns_theta_min 2.61 _diffrn_reflns_reduction_process ? _diffrn_ambient_temperature 293 _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector 'scintillation counter' _refine_ls_extinction_expression ? _refine_ls_matrix_type full _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_all .051 _refine_ls_wR_factor_all .059 _refine_ls_goodness_of_fit_all 1.115 _refine_ls_shift/su_mean .003 #========================================================================== # Structure Factor lists should be submitted as separate files #========================================================================== #data_<structure> # but for xtal use the refln data is needed in same block loop_ _refln_index_h _refln_index_k _refln_index_l _refln_F_meas _refln_F_calc _refln_F_sigma _refln_F_squared_meas _refln_F_squared_calc _refln_F_squared_sigma _refln_observed_status _refln_F_meas_friedel _refln_F_sigma_friedel _refln_F_squared_meas_friedel _refln_F_squared_sigma_friedel ? ? ? ? ? ? ? ? ? ? ? ? ? ? #===END data_cppji2 _database_code_CSD 211802 _audit_creation_method Xtal3.6 _audit_creation_date 03-03-18 _audit_update_record ? _chemical_formula_sum 'C6 H9 I3 N2 S1' _chemical_formula_moiety ? _chemical_formula_weight 521.93 _chemical_melting_point ? _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P_b_c_a _symmetry_space_group_name_Hall -p_2ac_2ab loop_ _symmetry_equiv_pos_as_xyz +x,+y,+z 1/2-x,-y,1/2+z 1/2+x,1/2-y,-z -x,1/2+y,1/2-z -x,-y,-z 1/2+x,+y,1/2-z 1/2-x,1/2+y,+z +x,1/2-y,1/2+z _cell_length_a 13.4200(10) _cell_length_b 12.9500(10) _cell_length_c 14.4390(10) _cell_angle_alpha 90.00000 _cell_angle_beta 90.00000 _cell_angle_gamma 90.00000 _cell_volume 2509.3(3) _cell_formula_units_Z 8 _exptl_crystal_density_diffrn 2.763 _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength .71073 _cell_measurement_reflns_used 4957 _cell_measurement_theta_min 2.60 _cell_measurement_theta_max 32.41 _cell_measurement_temperature 150 _exptl_absorpt_coefficient_mu 7.599 _exptl_crystal_description prism _exptl_crystal_size_max .27 _exptl_crystal_size_mid .21 _exptl_crystal_size_min .19 _exptl_crystal_size_rad ? _exptl_crystal_colour dark_red _diffrn_measurement_device_type ; Bruker SMART CCD diffractometer ; _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS; Sheldrick, 1996 ; _exptl_absorpt_correction_T_min .70 _exptl_absorpt_correction_T_max 1 _diffrn_reflns_number 40435 _reflns_number_total 4433 _reflns_Friedel_coverage 0 _reflns_number_gt 3303 _reflns_threshold_expression 'F > 4.00 sig(F )' _diffrn_reflns_theta_max 32.21 _diffrn_reflns_theta_full ? _diffrn_measured_fraction_theta_max ? _diffrn_measured_fraction_theta_full ? _diffrn_reflns_av_R_equivalents .053 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 21 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _refine_ls_structure_factor_coef F _refine_ls_R_factor_gt .037 _refine_ls_wR_factor_ref .044 _refine_ls_goodness_of_fit_ref 1.116 _refine_ls_number_reflns 3303 _refine_ls_number_parameters 109 _refine_ls_weighting_scheme calc _refine_ls_weighting_details ? _refine_ls_hydrogen_treatment noref _refine_ls_shift/su_max .003 _refine_diff_density_min -.892 _refine_diff_density_max 2.625 _refine_ls_extinction_method ? _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? # 3. Information for the "methods" section #----------------------------------------- _computing_data_collection 'Siemens SMART (Siemens, 1995)' _computing_cell_refinement 'Siemens SAINT (Siemens, 1995)' _computing_data_reduction 'xtal ADDREF SORTRF' _computing_structure_solution xtal _computing_structure_refinement 'xtal CRYLSQ' _computing_molecular_graphics xtal _computing_publication_material 'xtal BONDLA CIFIO' # 4. Supplementary data for validation and tables #------------------------------------------------ loop_ _atom_type_symbol _atom_type_description _atom_type_oxidation_number _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C ? 0 48 .002 .002 'Int Tables Vol IV Tables 2.2B and 2.3.1' H ? 0 72 0 0 'Int Tables Vol IV Tables 2.2B and 2.3.1' I ? 0 24 -.726 1.812 'Int Tables Vol IV Tables 2.2B and 2.3.1' N ? 0 16 .004 .003 'Int Tables Vol IV Tables 2.2B and 2.3.1' S ? 0 8 .11 .124 'Int Tables Vol IV Tables 2.2B and 2.3.1' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_calc_attached_atom _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group I1 .52931(3) .68750(3) .60979(2) .02932(16) Uani ? ? 1.00000 ? ? I2 .38307(2) .52681(2) .60202(2) .02192(14) Uani ? ? 1.00000 ? ? I3 .24215(2) .35045(3) .59785(2) .02693(16) Uani ? ? 1.00000 ? ? S1 .59038(9) .58742(10) .88263(10) .0295(6) Uani ? ? 1.00000 ? ? C2 .4989(4) .4921(4) .8798(4) .031(3) Uani ? ? 1.00000 ? ? C3 .4073(4) .5296(4) .8667(3) .025(2) Uani ? ? 1.00000 ? ? C31 .3111(4) .4739(5) .8621(4) .035(3) Uani ? ? 1.00000 ? ? N4 .4098(3) .6362(3) .8592(3) .0213(17) Uani ? ? 1.00000 ? ? C5 .3366(4) .7156(4) .8361(4) .031(2) Uani ? ? 1.00000 ? ? C6 .3960(4) .8154(4) .8490(4) .033(3) Uani ? ? 1.00000 ? ? N7 .4999(3) .7785(3) .8527(3) .030(2) Uani ? ? 1.00000 ? ? C8 .4994(3) .6778(4) .8661(3) .023(2) Uani ? ? 1.00000 ? ? H2 .50441 .43221 .88934 .08400 Uiso ? ? 1.00000 ? ? H31a .26921 .49976 .90944 .09800 Uiso ? ? 1.00000 ? ? H31b .32526 .40671 .88285 .03000 Uiso ? ? 1.00000 ? ? H31c .27684 .47686 .79789 .07800 Uiso ? ? 1.00000 ? ? H5a .28186 .71390 .87610 .02300 Uiso ? ? 1.00000 ? ? H5b .31671 .70550 .77538 .01100 Uiso ? ? 1.00000 ? ? H6a .37886 .85906 .89969 .06900 Uiso ? ? 1.00000 ? ? H6b .38566 .86420 .78817 .07700 Uiso ? ? 1.00000 ? ? H7 .53933 .81403 .86475 .01900 Uiso ? ? 1.00000 ? ? loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 I1 .03279(17) .02515(15) .03001(17) -.00425(12) .00334(13) -.00375(12) I2 .02468(14) .02004(13) .02104(14) .00247(10) .00295(10) .00094(10) I3 .02413(15) .02654(16) .03013(17) -.00257(11) .00345(11) .00230(12) S1 .0232(5) .0275(6) .0378(7) .0023(5) -.0025(5) .0033(5) C2 .034(3) .025(2) .035(3) .001(2) -.003(2) .005(2) C3 .030(2) .023(2) .021(2) -.0048(18) .0023(18) -.0014(17) C31 .036(3) .038(3) .032(3) -.012(2) .004(2) .001(2) N4 .0224(17) .0229(18) .0184(17) -.0004(15) -.0010(14) -.0002(14) C5 .028(2) .036(3) .029(2) .006(2) -.001(2) -.001(2) C6 .033(3) .031(2) .036(3) .008(2) -.007(2) -.007(2) N7 .033(2) .0233(19) .033(2) -.0027(17) -.0059(18) -.0034(17) C8 .025(2) .025(2) .019(2) .0010(17) -.0025(16) -.0031(17) # 5. Molecular Geometry #---------------------- loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag #<< enter YES for value to be published I1 I2 . . 2.8627(5) ? I2 I3 . . 2.9657(5) ? S1 C2 . . 1.741(5) ? S1 C8 . . 1.708(5) ? C2 C3 . . 1.335(7) ? C2 H2 . . .792 ? C3 C31 . . 1.480(8) ? C3 N4 . . 1.385(6) ? C31 H31a . . .946 ? C31 H31b . . .940 ? C31 H31c . . 1.036 ? N4 C5 . . 1.461(7) ? N4 C8 . . 1.321(6) ? C5 C6 . . 1.529(8) ? C5 H5a . . .935 ? C5 H5b . . .926 ? C6 N7 . . 1.475(7) ? C6 H6a . . .953 ? C6 H6b . . 1.091 ? N7 C8 . . 1.319(6) ? N7 H7 . . .722 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag #<< enter YES for value to be published I1 I2 I3 . . . 176.15(2) ? C2 S1 C8 . . . 88.7(2) ? S1 C2 C3 . . . 113.3(4) ? S1 C2 H2 . . . 128.7 ? C3 C2 H2 . . . 117.8 ? C2 C3 C31 . . . 129.2(5) ? C2 C3 N4 . . . 110.6(4) ? C31 C3 N4 . . . 120.2(4) ? C3 C31 H31a . . . 108.3 ? C3 C31 H31b . . . 105.1 ? C3 C31 H31c . . . 114.2 ? H31a C31 H31b . . . 102.6 ? H31a C31 H31c . . . 111.7 ? H31b C31 H31c . . . 114.1 ? C3 N4 C5 . . . 134.7(4) ? C3 N4 C8 . . . 115.0(4) ? C5 N4 C8 . . . 110.0(4) ? N4 C5 C6 . . . 102.5(4) ? N4 C5 H5a . . . 111.7 ? N4 C5 H5b . . . 108.1 ? C6 C5 H5a . . . 110.8 ? C6 C5 H5b . . . 112.7 ? H5a C5 H5b . . . 110.8 ? C5 C6 N7 . . . 103.0(4) ? C5 C6 H6a . . . 118.0 ? C5 C6 H6b . . . 109.0 ? N7 C6 H6a . . . 113.1 ? N7 C6 H6b . . . 109.6 ? H6a C6 H6b . . . 104.1 ? C6 N7 C8 . . . 108.6(4) ? C6 N7 H7 . . . 119.7 ? C8 N7 H7 . . . 126.7 ? S1 C8 N4 . . . 112.4(3) ? S1 C8 N7 . . . 134.0(4) ? N4 C8 N7 . . . 113.4(4) ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag #<< enter YES for value to be published ? ? ? ? ? ? ? ? ? ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_D _geom_hbond_site_symmetry_H _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag #<< enter YES for value to be published ? ? ? ? ? ? ? ? ? ? ? #-------------------------------------------------------------------------- # Special items requested by author for inclusion in paper #-------------------------------------------------------------------------- loop_ _publ_manuscript_incl_extra_item _publ_manuscript_incl_extra_defn ? ? #-------------------------------------------------------------------------- # Items which are non-mandatory for Acta C submissions #-------------------------------------------------------------------------- _atom_sites_solution_primary ? _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens ? _geom_special_details ? _cell_special_details ; ? ; _exptl_special_details ; ? ; _diffrn_special_details ; ? ; _chemical_compound_source ? _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_analytical ? _chemical_formula_structural ? _exptl_crystal_F_000 1872 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? loop_ _diffrn_attenuator_code _diffrn_attenuator_scale ? ? _reflns_limit_h_min 0 _reflns_limit_h_max 20 _reflns_limit_k_min 0 _reflns_limit_k_max 19 _reflns_limit_l_min 0 _reflns_limit_l_max 21 _reflns_number_observed ? _reflns_d_resolution_high .667 _reflns_d_resolution_low 7.817 _diffrn_reflns_av_sigmaI/netI .059 _diffrn_reflns_theta_min 2.6 _diffrn_reflns_reduction_process ? _diffrn_ambient_temperature 150 _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector 'CCD area detector' _refine_ls_extinction_expression ? _refine_ls_matrix_type full _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_all .059 _refine_ls_wR_factor_all .049 _refine_ls_goodness_of_fit_all 1.066 _refine_ls_shift/su_mean .0002 #========================================================================== # Structure Factor lists should be submitted as separate files #========================================================================== #data_<structure> # but for xtal use the refln data is needed in same block loop_ _refln_index_h _refln_index_k _refln_index_l _refln_F_meas _refln_F_calc _refln_F_sigma _refln_F_squared_meas _refln_F_squared_calc _refln_F_squared_sigma _refln_observed_status _refln_F_meas_friedel _refln_F_sigma_friedel _refln_F_squared_meas_friedel _refln_F_squared_sigma_friedel ? ? ? ? ? ? ? ? ? ? ? ? ? ? #===END