# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'J Rawson' _publ_contact_author_email JMR31@CAM.AC.UK _publ_section_title ; Formation of N-bridgehead 1,2,5-thiadiazolium and selenadiazolium rings through an intramolecular cyclisation reaction ; loop_ _publ_author_name 'J Rawson' 'Catherine E. Bacon' 'Dana Eisler' 'Rebecca L. Melen' # Attachment 'jr0708a.cif' data_jr0708a _database_code_depnum_ccdc_archive 'CCDC 691668' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H10 Cl N3 O S' _chemical_formula_sum 'C11 H10 Cl N3 O S' _chemical_formula_weight 267.73 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c _symmetry_space_group_name_Hall -C2yc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 24.1059(6) _cell_length_b 4.9368(2) _cell_length_c 20.7418(6) _cell_angle_alpha 90.00 _cell_angle_beta 111.0242(16) _cell_angle_gamma 90.00 _cell_volume 2304.07(13) _cell_formula_units_Z 8 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 7515 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description plate _exptl_crystal_colour orange _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.544 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1104 _exptl_absorpt_coefficient_mu 0.498 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.875 _exptl_absorpt_correction_T_max 0.961 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 9748 _diffrn_reflns_av_R_equivalents 0.0507 _diffrn_reflns_av_sigmaI/netI 0.0482 _diffrn_reflns_limit_h_min -30 _diffrn_reflns_limit_h_max 29 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.23 _diffrn_reflns_theta_max 27.49 _reflns_number_total 2635 _reflns_number_gt 1982 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SHELXL-97 (Sheldrick 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _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. H atomsadded at calculated positions except water H atoms which were located in difference map and refined with restrained O-H distances. ; _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^)+(0.0285P)^2^+3.3848P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2635 _refine_ls_number_parameters 162 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0626 _refine_ls_R_factor_gt 0.0388 _refine_ls_wR_factor_ref 0.0884 _refine_ls_wR_factor_gt 0.0794 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.021 _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 N1 N 0.52316(8) 0.2492(4) 0.45092(8) 0.0249(4) Uani 1 1 d . . . S1 S 0.58043(2) 0.44545(12) 0.48516(3) 0.02534(15) Uani 1 1 d . . . N2 N 0.61813(7) 0.3066(4) 0.43642(8) 0.0222(4) Uani 1 1 d . . . C1 C 0.67375(9) 0.3733(5) 0.43889(11) 0.0262(5) Uani 1 1 d . . . H1A H 0.6959 0.5120 0.4689 0.031 Uiso 1 1 calc R . . C2 C 0.69691(10) 0.2360(5) 0.39709(11) 0.0299(5) Uani 1 1 d . . . H2A H 0.7356 0.2790 0.3981 0.036 Uiso 1 1 calc R . . C3 C 0.66407(10) 0.0326(5) 0.35282(11) 0.0307(5) Uani 1 1 d . . . H3A H 0.6805 -0.0611 0.3238 0.037 Uiso 1 1 calc R . . C4 C 0.60821(9) -0.0316(5) 0.35120(11) 0.0270(5) Uani 1 1 d . . . H4A H 0.5857 -0.1687 0.3209 0.032 Uiso 1 1 calc R . . C5 C 0.58480(9) 0.1059(4) 0.39436(10) 0.0223(4) Uani 1 1 d . . . C6 C 0.52880(9) 0.0804(4) 0.40480(10) 0.0221(4) Uani 1 1 d . . . C7 C 0.47992(9) -0.1075(4) 0.36796(10) 0.0223(5) Uani 1 1 d . . . C8 C 0.42549(9) -0.0862(5) 0.37597(10) 0.0260(5) Uani 1 1 d . . . H8A H 0.4189 0.0500 0.4048 0.031 Uiso 1 1 calc R . . C9 C 0.38091(9) -0.2664(5) 0.34132(11) 0.0289(5) Uani 1 1 d . . . H9A H 0.3433 -0.2570 0.3463 0.035 Uiso 1 1 calc R . . C10 C 0.39191(9) -0.4609(5) 0.29928(11) 0.0280(5) Uani 1 1 d . . . H10A H 0.3620 -0.5866 0.2745 0.034 Uiso 1 1 calc R . . C11 C 0.44753(9) -0.4671(5) 0.29431(11) 0.0272(5) Uani 1 1 d . . . H11A H 0.4549 -0.6008 0.2654 0.033 Uiso 1 1 calc R . . N3 N 0.49180(7) -0.2959(4) 0.32775(8) 0.0244(4) Uani 1 1 d . . . O1 O 0.76072(8) 0.7421(4) 0.28243(9) 0.0401(4) Uani 1 1 d D . . H1C H 0.7538(14) 0.587(3) 0.2643(15) 0.066(10) Uiso 1 1 d D . . H1B H 0.7773(12) 0.716(7) 0.3255(6) 0.065(10) Uiso 1 1 d D . . Cl1 Cl 0.68040(2) 0.83197(12) 0.55615(3) 0.03117(16) 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 N1 0.0238(9) 0.0261(10) 0.0246(9) -0.0017(8) 0.0086(7) -0.0033(8) S1 0.0248(3) 0.0265(3) 0.0250(3) -0.0045(2) 0.0092(2) -0.0035(2) N2 0.0216(9) 0.0218(10) 0.0221(8) 0.0005(7) 0.0065(7) -0.0001(7) C1 0.0221(10) 0.0261(12) 0.0278(11) 0.0007(9) 0.0056(9) -0.0033(9) C2 0.0242(11) 0.0326(13) 0.0337(12) -0.0011(10) 0.0114(9) -0.0032(10) C3 0.0289(11) 0.0329(13) 0.0339(12) -0.0053(10) 0.0157(10) -0.0021(10) C4 0.0262(11) 0.0270(12) 0.0275(11) -0.0053(10) 0.0093(9) -0.0038(10) C5 0.0226(10) 0.0207(11) 0.0212(10) 0.0017(8) 0.0049(8) -0.0024(9) C6 0.0226(10) 0.0213(11) 0.0209(10) 0.0031(9) 0.0061(8) -0.0011(9) C7 0.0233(10) 0.0220(12) 0.0202(10) 0.0032(8) 0.0061(8) -0.0013(9) C8 0.0240(11) 0.0278(12) 0.0263(11) 0.0004(9) 0.0090(9) -0.0011(9) C9 0.0215(10) 0.0319(13) 0.0319(11) 0.0031(10) 0.0078(9) -0.0010(10) C10 0.0244(11) 0.0270(12) 0.0277(11) 0.0012(10) 0.0034(9) -0.0069(10) C11 0.0296(11) 0.0266(12) 0.0245(10) -0.0017(9) 0.0087(9) -0.0053(10) N3 0.0232(9) 0.0243(10) 0.0251(9) -0.0018(8) 0.0080(7) -0.0031(8) O1 0.0461(10) 0.0323(11) 0.0333(10) 0.0016(9) 0.0037(8) -0.0007(8) Cl1 0.0297(3) 0.0323(3) 0.0314(3) -0.0066(2) 0.0108(2) -0.0060(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 N1 C6 1.312(3) . ? N1 S1 1.6266(18) . ? S1 N2 1.7253(18) . ? N2 C1 1.364(3) . ? N2 C5 1.373(3) . ? C1 C2 1.368(3) . ? C1 H1A 0.9500 . ? C2 C3 1.399(3) . ? C2 H2A 0.9500 . ? C3 C4 1.372(3) . ? C3 H3A 0.9500 . ? C4 C5 1.394(3) . ? C4 H4A 0.9500 . ? C5 C6 1.447(3) . ? C6 C7 1.479(3) . ? C7 N3 1.347(3) . ? C7 C8 1.384(3) . ? C8 C9 1.381(3) . ? C8 H8A 0.9500 . ? C9 C10 1.385(3) . ? C9 H9A 0.9500 . ? C10 C11 1.382(3) . ? C10 H10A 0.9500 . ? C11 N3 1.343(3) . ? C11 H11A 0.9500 . ? O1 H1C 0.843(10) . ? O1 H1B 0.847(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 C6 N1 S1 113.76(14) . . ? N1 S1 N2 92.89(9) . . ? C1 N2 C5 122.79(18) . . ? C1 N2 S1 126.83(15) . . ? C5 N2 S1 110.36(13) . . ? N2 C1 C2 118.4(2) . . ? N2 C1 H1A 120.8 . . ? C2 C1 H1A 120.8 . . ? C1 C2 C3 120.6(2) . . ? C1 C2 H2A 119.7 . . ? C3 C2 H2A 119.7 . . ? C4 C3 C2 120.1(2) . . ? C4 C3 H3A 120.0 . . ? C2 C3 H3A 120.0 . . ? C3 C4 C5 119.4(2) . . ? C3 C4 H4A 120.3 . . ? C5 C4 H4A 120.3 . . ? N2 C5 C4 118.69(18) . . ? N2 C5 C6 109.42(17) . . ? C4 C5 C6 131.89(19) . . ? N1 C6 C5 113.57(18) . . ? N1 C6 C7 120.21(18) . . ? C5 C6 C7 126.20(18) . . ? N3 C7 C8 123.23(19) . . ? N3 C7 C6 116.48(18) . . ? C8 C7 C6 120.29(19) . . ? C9 C8 C7 118.8(2) . . ? C9 C8 H8A 120.6 . . ? C7 C8 H8A 120.6 . . ? C8 C9 C10 119.0(2) . . ? C8 C9 H9A 120.5 . . ? C10 C9 H9A 120.5 . . ? C11 C10 C9 118.2(2) . . ? C11 C10 H10A 120.9 . . ? C9 C10 H10A 120.9 . . ? N3 C11 C10 124.1(2) . . ? N3 C11 H11A 118.0 . . ? C10 C11 H11A 118.0 . . ? C11 N3 C7 116.63(18) . . ? H1C O1 H1B 106(3) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.298 _refine_diff_density_min -0.257 _refine_diff_density_rms 0.061 # Attachment 'jr0723.cif' data_jr0723 _database_code_depnum_ccdc_archive 'CCDC 691669' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H11 N5 O4 S' _chemical_formula_sum 'C17 H11 N5 O4 S' _chemical_formula_weight 381.37 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c _symmetry_space_group_name_Hall -C2yc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 18.4166(3) _cell_length_b 6.48490(10) _cell_length_c 27.9654(6) _cell_angle_alpha 90.00 _cell_angle_beta 100.4673(7) _cell_angle_gamma 90.00 _cell_volume 3284.32(10) _cell_formula_units_Z 8 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 38803 _cell_measurement_theta_min 1.02 _cell_measurement_theta_max 27.48 _exptl_crystal_description plate _exptl_crystal_colour orange _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.543 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1568 _exptl_absorpt_coefficient_mu 0.234 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.760 _exptl_absorpt_correction_T_max 0.997 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 13597 _diffrn_reflns_av_R_equivalents 0.0561 _diffrn_reflns_av_sigmaI/netI 0.0438 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_limit_l_max 36 _diffrn_reflns_theta_min 2.91 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3728 _reflns_number_gt 3141 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SHELXL-97 (Sheldrick 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _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^)+(0.0298P)^2^+3.2452P] 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 3728 _refine_ls_number_parameters 244 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0528 _refine_ls_R_factor_gt 0.0406 _refine_ls_wR_factor_ref 0.0967 _refine_ls_wR_factor_gt 0.0904 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.058 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.59917(2) 0.53639(6) 0.461487(15) 0.02789(12) Uani 1 1 d . . . N1 N 0.62382(7) 0.4331(2) 0.41170(5) 0.0278(3) Uani 1 1 d . . . C1 C 0.60077(9) 0.5033(2) 0.36840(6) 0.0268(3) Uani 1 1 d . . . C2 C 0.62948(9) 0.3910(3) 0.32903(6) 0.0274(3) Uani 1 1 d . . . C3 C 0.65938(10) 0.1935(3) 0.33697(6) 0.0327(4) Uani 1 1 d . . . H3A H 0.6593 0.1251 0.3670 0.039 Uiso 1 1 calc R . . C4 C 0.68902(10) 0.0986(3) 0.30078(7) 0.0371(4) Uani 1 1 d . . . H4A H 0.7099 -0.0354 0.3056 0.044 Uiso 1 1 calc R . . C5 C 0.68779(10) 0.2016(3) 0.25747(7) 0.0373(4) Uani 1 1 d . . . H5A H 0.7084 0.1411 0.2320 0.045 Uiso 1 1 calc R . . C6 C 0.65589(10) 0.3948(3) 0.25203(6) 0.0352(4) Uani 1 1 d . . . H6A H 0.6542 0.4638 0.2219 0.042 Uiso 1 1 calc R . . N2 N 0.62708(8) 0.4910(2) 0.28673(5) 0.0323(3) Uani 1 1 d . . . C7 C 0.55023(9) 0.6826(3) 0.35659(6) 0.0278(3) Uani 1 1 d . . . C8 C 0.49920(10) 0.6952(3) 0.31357(7) 0.0376(4) Uani 1 1 d . . . H8A H 0.4962 0.5894 0.2898 0.045 Uiso 1 1 calc R . . C9 C 0.45292(11) 0.8636(3) 0.30592(7) 0.0450(5) Uani 1 1 d . . . H9A H 0.4178 0.8761 0.2766 0.054 Uiso 1 1 calc R . . C10 C 0.45812(10) 1.0138(3) 0.34123(7) 0.0411(4) Uani 1 1 d . . . H10A H 0.4277 1.1330 0.3365 0.049 Uiso 1 1 calc R . . C11 C 0.50883(10) 0.9866(3) 0.38380(7) 0.0371(4) Uani 1 1 d . . . H11A H 0.5113 1.0878 0.4086 0.045 Uiso 1 1 calc R . . N3 N 0.55449(8) 0.8249(2) 0.39173(5) 0.0327(3) Uani 1 1 d . . . C12 C 0.63170(8) 0.3311(2) 0.50153(6) 0.0262(3) Uani 1 1 d . . . C13 C 0.63182(9) 0.3417(2) 0.55184(6) 0.0278(3) Uani 1 1 d . . . C14 C 0.66161(9) 0.1886(3) 0.58421(6) 0.0301(4) Uani 1 1 d . . . H14A H 0.6617 0.2015 0.6181 0.036 Uiso 1 1 calc R . . C15 C 0.69100(9) 0.0180(2) 0.56579(6) 0.0278(3) Uani 1 1 d . . . C16 C 0.68999(9) -0.0045(3) 0.51645(6) 0.0297(4) Uani 1 1 d . . . H16A H 0.7092 -0.1259 0.5043 0.036 Uiso 1 1 calc R . . C17 C 0.66098(9) 0.1503(3) 0.48514(6) 0.0297(4) Uani 1 1 d . . . H17A H 0.6608 0.1343 0.4514 0.036 Uiso 1 1 calc R . . N4 N 0.59975(8) 0.5184(2) 0.57277(5) 0.0332(3) Uani 1 1 d . . . O1 O 0.57353(7) 0.65758(19) 0.54507(5) 0.0391(3) Uani 1 1 d . . . O2 O 0.60021(9) 0.5210(2) 0.61681(5) 0.0504(4) Uani 1 1 d . . . N5 N 0.72237(8) -0.1460(2) 0.59915(5) 0.0326(3) Uani 1 1 d . . . O3 O 0.72122(8) -0.1242(2) 0.64264(5) 0.0437(3) Uani 1 1 d . . . O4 O 0.74807(7) -0.2989(2) 0.58195(5) 0.0392(3) 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 S1 0.0320(2) 0.0266(2) 0.0251(2) -0.00195(16) 0.00502(16) 0.00153(16) N1 0.0311(7) 0.0264(7) 0.0257(7) -0.0014(5) 0.0049(6) -0.0002(5) C1 0.0272(8) 0.0262(8) 0.0270(8) -0.0008(6) 0.0044(6) -0.0027(6) C2 0.0274(8) 0.0289(8) 0.0250(8) -0.0004(6) 0.0028(6) -0.0023(6) C3 0.0405(9) 0.0306(9) 0.0273(9) 0.0011(7) 0.0065(7) 0.0019(7) C4 0.0448(10) 0.0330(10) 0.0339(10) -0.0021(7) 0.0085(8) 0.0062(8) C5 0.0374(10) 0.0461(11) 0.0289(9) -0.0062(8) 0.0077(7) 0.0013(8) C6 0.0373(9) 0.0450(11) 0.0234(8) 0.0026(7) 0.0057(7) 0.0007(8) N2 0.0347(8) 0.0350(8) 0.0268(7) 0.0029(6) 0.0050(6) 0.0025(6) C7 0.0285(8) 0.0283(8) 0.0265(8) 0.0016(6) 0.0048(6) 0.0001(6) C8 0.0389(10) 0.0435(11) 0.0292(9) -0.0032(8) 0.0030(7) 0.0068(8) C9 0.0415(10) 0.0553(13) 0.0359(11) 0.0029(9) 0.0010(8) 0.0153(9) C10 0.0396(10) 0.0388(11) 0.0457(11) 0.0075(8) 0.0098(8) 0.0112(8) C11 0.0388(10) 0.0301(9) 0.0430(11) -0.0022(8) 0.0085(8) 0.0022(7) N3 0.0341(7) 0.0286(8) 0.0344(8) -0.0026(6) 0.0036(6) 0.0012(6) C12 0.0261(8) 0.0283(8) 0.0243(8) -0.0020(6) 0.0049(6) -0.0034(6) C13 0.0306(8) 0.0275(8) 0.0265(8) -0.0052(6) 0.0082(7) -0.0042(6) C14 0.0340(9) 0.0325(9) 0.0246(8) -0.0032(7) 0.0069(7) -0.0073(7) C15 0.0301(8) 0.0267(8) 0.0259(8) 0.0019(6) 0.0031(6) -0.0031(6) C16 0.0344(9) 0.0272(9) 0.0277(8) -0.0028(6) 0.0057(7) 0.0009(6) C17 0.0361(9) 0.0293(9) 0.0232(8) -0.0027(6) 0.0043(7) 0.0015(7) N4 0.0402(8) 0.0306(8) 0.0318(8) -0.0058(6) 0.0150(6) -0.0055(6) O1 0.0477(8) 0.0303(7) 0.0414(8) -0.0012(6) 0.0142(6) 0.0055(5) O2 0.0824(11) 0.0422(8) 0.0333(8) -0.0067(6) 0.0280(7) 0.0019(7) N5 0.0327(8) 0.0349(8) 0.0289(8) 0.0034(6) 0.0022(6) -0.0050(6) O3 0.0553(8) 0.0489(8) 0.0255(7) 0.0062(6) 0.0037(6) -0.0011(6) O4 0.0439(7) 0.0332(7) 0.0398(8) 0.0041(6) 0.0060(6) 0.0053(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 N1 1.6803(14) . ? S1 C12 1.7723(17) . ? N1 C1 1.291(2) . ? C1 C7 1.488(2) . ? C1 C2 1.495(2) . ? C2 N2 1.343(2) . ? C2 C3 1.396(2) . ? C3 C4 1.379(2) . ? C3 H3A 0.9500 . ? C4 C5 1.380(3) . ? C4 H4A 0.9500 . ? C5 C6 1.380(3) . ? C5 H5A 0.9500 . ? C6 N2 1.341(2) . ? C6 H6A 0.9500 . ? C7 N3 1.340(2) . ? C7 C8 1.388(2) . ? C8 C9 1.378(3) . ? C8 H8A 0.9500 . ? C9 C10 1.378(3) . ? C9 H9A 0.9500 . ? C10 C11 1.384(3) . ? C10 H10A 0.9500 . ? C11 N3 1.337(2) . ? C11 H11A 0.9500 . ? C12 C17 1.402(2) . ? C12 C13 1.408(2) . ? C13 C14 1.387(2) . ? C13 N4 1.460(2) . ? C14 C15 1.373(2) . ? C14 H14A 0.9500 . ? C15 C16 1.384(2) . ? C15 N5 1.463(2) . ? C16 C17 1.375(2) . ? C16 H16A 0.9500 . ? C17 H17A 0.9500 . ? N4 O1 1.2296(19) . ? N4 O2 1.2300(18) . ? N5 O3 1.2283(18) . ? N5 O4 1.2335(19) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 S1 C12 96.48(7) . . ? C1 N1 S1 122.97(12) . . ? N1 C1 C7 124.71(15) . . ? N1 C1 C2 114.76(14) . . ? C7 C1 C2 120.52(14) . . ? N2 C2 C3 122.17(15) . . ? N2 C2 C1 117.00(14) . . ? C3 C2 C1 120.80(15) . . ? C4 C3 C2 119.34(16) . . ? C4 C3 H3A 120.3 . . ? C2 C3 H3A 120.3 . . ? C3 C4 C5 118.85(17) . . ? C3 C4 H4A 120.6 . . ? C5 C4 H4A 120.6 . . ? C4 C5 C6 118.35(17) . . ? C4 C5 H5A 120.8 . . ? C6 C5 H5A 120.8 . . ? N2 C6 C5 123.98(17) . . ? N2 C6 H6A 118.0 . . ? C5 C6 H6A 118.0 . . ? C6 N2 C2 117.29(15) . . ? N3 C7 C8 122.38(16) . . ? N3 C7 C1 115.11(14) . . ? C8 C7 C1 122.40(15) . . ? C9 C8 C7 118.90(18) . . ? C9 C8 H8A 120.5 . . ? C7 C8 H8A 120.5 . . ? C10 C9 C8 119.25(18) . . ? C10 C9 H9A 120.4 . . ? C8 C9 H9A 120.4 . . ? C9 C10 C11 118.30(17) . . ? C9 C10 H10A 120.8 . . ? C11 C10 H10A 120.8 . . ? N3 C11 C10 123.27(18) . . ? N3 C11 H11A 118.4 . . ? C10 C11 H11A 118.4 . . ? C11 N3 C7 117.85(15) . . ? C17 C12 C13 115.87(15) . . ? C17 C12 S1 121.85(13) . . ? C13 C12 S1 122.25(13) . . ? C14 C13 C12 123.06(15) . . ? C14 C13 N4 116.17(15) . . ? C12 C13 N4 120.77(15) . . ? C15 C14 C13 117.91(15) . . ? C15 C14 H14A 121.0 . . ? C13 C14 H14A 121.0 . . ? C14 C15 C16 121.62(16) . . ? C14 C15 N5 118.94(15) . . ? C16 C15 N5 119.42(15) . . ? C17 C16 C15 119.40(16) . . ? C17 C16 H16A 120.3 . . ? C15 C16 H16A 120.3 . . ? C16 C17 C12 122.06(16) . . ? C16 C17 H17A 119.0 . . ? C12 C17 H17A 119.0 . . ? O1 N4 O2 123.45(15) . . ? O1 N4 C13 117.70(14) . . ? O2 N4 C13 118.85(15) . . ? O3 N5 O4 123.74(15) . . ? O3 N5 C15 118.16(15) . . ? O4 N5 C15 118.10(14) . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.200 _refine_diff_density_min -0.345 _refine_diff_density_rms 0.049 # Attachment 'jr0807.cif' data_jr0807 _database_code_depnum_ccdc_archive 'CCDC 691670' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H9 Cl N2 Se' _chemical_formula_sum 'C12 H9 Cl N2 Se' _chemical_formula_weight 295.62 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Tetragonal _symmetry_space_group_name_H-M P43212 _symmetry_space_group_name_Hall P4nw2abw loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-y+1/2, x+1/2, z+3/4' 'y+1/2, -x+1/2, z+1/4' '-x+1/2, y+1/2, -z+3/4' 'x+1/2, -y+1/2, -z+1/4' 'y, x, -z' '-y, -x, -z+1/2' _cell_length_a 8.27180(10) _cell_length_b 8.27180(10) _cell_length_c 33.0787(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2263.33(6) _cell_formula_units_Z 8 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 27337 _cell_measurement_theta_min 1.02 _cell_measurement_theta_max 27.48 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.735 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1168 _exptl_absorpt_coefficient_mu 3.524 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.678 _exptl_absorpt_correction_T_max 0.855 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 10232 _diffrn_reflns_av_R_equivalents 0.0552 _diffrn_reflns_av_sigmaI/netI 0.0427 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 41 _diffrn_reflns_theta_min 2.75 _diffrn_reflns_theta_max 26.33 _reflns_number_total 2314 _reflns_number_gt 2078 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SHELXL-97 (Sheldrick 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _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. Flack parameter based on Friedel pairs consistent with correct absolute structure. ; _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^)+(0.0134P)^2^+4.4628P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.019(19) _refine_ls_number_reflns 2314 _refine_ls_number_parameters 145 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0505 _refine_ls_R_factor_gt 0.0412 _refine_ls_wR_factor_ref 0.0853 _refine_ls_wR_factor_gt 0.0816 _refine_ls_goodness_of_fit_ref 1.190 _refine_ls_restrained_S_all 1.190 _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 Se1 Se 0.60735(6) 0.46002(6) 0.104277(17) 0.03203(14) Uani 1 1 d . . . Cl1 Cl 0.33703(16) 0.32955(16) 0.11898(5) 0.0436(4) Uani 1 1 d . . . N1 N 0.4972(4) 0.6150(5) 0.07668(12) 0.0312(10) Uani 1 1 d . . . C1 C 0.5848(6) 0.7299(6) 0.06203(15) 0.0309(11) Uani 1 1 d . . . C2 C 0.5051(6) 0.8529(6) 0.03587(15) 0.0296(11) Uani 1 1 d . . . C3 C 0.5224(7) 1.0175(6) 0.04220(17) 0.0377(13) Uani 1 1 d . . . H3A H 0.5893 1.0565 0.0634 0.045 Uiso 1 1 calc R . . C4 C 0.4412(7) 1.1244(7) 0.01724(18) 0.0422(14) Uani 1 1 d . . . H4A H 0.4496 1.2373 0.0221 0.051 Uiso 1 1 calc R . . C5 C 0.3485(7) 1.0695(7) -0.01444(18) 0.0420(14) Uani 1 1 d . . . H5A H 0.2969 1.1443 -0.0320 0.050 Uiso 1 1 calc R . . C6 C 0.3307(6) 0.9072(7) -0.02056(17) 0.0388(13) Uani 1 1 d . . . H6A H 0.2652 0.8696 -0.0422 0.047 Uiso 1 1 calc R . . C7 C 0.4069(6) 0.7974(7) 0.00435(17) 0.0368(13) Uani 1 1 d . . . H7A H 0.3927 0.6847 0.0001 0.044 Uiso 1 1 calc R . . C8 C 0.7593(6) 0.7279(6) 0.06880(15) 0.0301(11) Uani 1 1 d . . . C9 C 0.8768(7) 0.8338(6) 0.05501(15) 0.0353(12) Uani 1 1 d . . . H9A H 0.8478 0.9284 0.0404 0.042 Uiso 1 1 calc R . . C10 C 1.0364(7) 0.7990(6) 0.06289(16) 0.0392(13) Uani 1 1 d . . . H10A H 1.1187 0.8691 0.0532 0.047 Uiso 1 1 calc R . . C11 C 1.0776(6) 0.6642(7) 0.08464(16) 0.0361(13) Uani 1 1 d . . . H11A H 1.1878 0.6409 0.0902 0.043 Uiso 1 1 calc R . . C12 C 0.9584(6) 0.5635(6) 0.09817(16) 0.0347(12) Uani 1 1 d . . . H12A H 0.9864 0.4699 0.1132 0.042 Uiso 1 1 calc R . . N2 N 0.8019(4) 0.5952(5) 0.09043(13) 0.0290(10) 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 Se1 0.0282(3) 0.0293(3) 0.0386(3) 0.0015(2) 0.0009(2) 0.0012(2) Cl1 0.0365(7) 0.0358(7) 0.0585(9) 0.0101(6) 0.0049(6) -0.0027(6) N1 0.028(2) 0.030(2) 0.036(2) 0.0007(19) 0.0013(17) 0.0014(17) C1 0.029(3) 0.030(3) 0.033(3) -0.003(2) -0.001(2) -0.0008(19) C2 0.021(3) 0.032(3) 0.036(3) 0.001(2) 0.004(2) 0.0022(19) C3 0.034(3) 0.036(3) 0.042(3) 0.001(3) 0.005(3) -0.001(2) C4 0.042(3) 0.030(3) 0.055(4) 0.007(3) 0.009(3) 0.002(2) C5 0.037(3) 0.044(4) 0.046(3) 0.008(3) 0.006(3) 0.014(2) C6 0.031(3) 0.050(3) 0.036(3) 0.001(3) -0.004(2) 0.004(3) C7 0.038(3) 0.033(3) 0.040(3) 0.000(2) 0.002(3) 0.002(2) C8 0.032(3) 0.025(3) 0.033(3) -0.003(2) 0.001(2) 0.000(2) C9 0.039(3) 0.032(3) 0.034(3) -0.001(2) 0.007(3) -0.006(2) C10 0.037(3) 0.040(3) 0.040(3) -0.008(3) 0.008(3) -0.009(2) C11 0.026(3) 0.043(3) 0.039(3) -0.012(3) 0.001(2) 0.006(2) C12 0.035(3) 0.032(3) 0.038(3) -0.010(2) -0.002(2) 0.000(2) N2 0.019(2) 0.032(2) 0.035(2) -0.0058(19) 0.0022(17) -0.0017(17) _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 Se1 N1 1.819(4) . ? Se1 N2 2.013(4) . ? Se1 Cl1 2.5300(14) . ? N1 C1 1.290(6) . ? C1 C8 1.461(7) . ? C1 C2 1.490(7) . ? C2 C3 1.385(7) . ? C2 C7 1.399(7) . ? C3 C4 1.384(7) . ? C3 H3A 0.9500 . ? C4 C5 1.376(8) . ? C4 H4A 0.9500 . ? C5 C6 1.366(8) . ? C5 H5A 0.9500 . ? C6 C7 1.379(7) . ? C6 H6A 0.9500 . ? C7 H7A 0.9500 . ? C8 N2 1.357(6) . ? C8 C9 1.386(7) . ? C9 C10 1.376(8) . ? C9 H9A 0.9500 . ? C10 C11 1.370(8) . ? C10 H10A 0.9500 . ? C11 C12 1.365(7) . ? C11 H11A 0.9500 . ? C12 N2 1.345(6) . ? C12 H12A 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Se1 N2 83.95(17) . . ? N1 Se1 Cl1 87.39(12) . . ? N2 Se1 Cl1 170.93(12) . . ? C1 N1 Se1 115.2(3) . . ? N1 C1 C8 119.3(5) . . ? N1 C1 C2 118.2(4) . . ? C8 C1 C2 122.3(4) . . ? C3 C2 C7 119.7(5) . . ? C3 C2 C1 122.5(5) . . ? C7 C2 C1 117.8(4) . . ? C4 C3 C2 119.2(5) . . ? C4 C3 H3A 120.4 . . ? C2 C3 H3A 120.4 . . ? C5 C4 C3 121.0(5) . . ? C5 C4 H4A 119.5 . . ? C3 C4 H4A 119.5 . . ? C6 C5 C4 119.8(6) . . ? C6 C5 H5A 120.1 . . ? C4 C5 H5A 120.1 . . ? C5 C6 C7 120.7(6) . . ? C5 C6 H6A 119.7 . . ? C7 C6 H6A 119.7 . . ? C6 C7 C2 119.6(5) . . ? C6 C7 H7A 120.2 . . ? C2 C7 H7A 120.2 . . ? N2 C8 C9 120.2(5) . . ? N2 C8 C1 110.3(4) . . ? C9 C8 C1 129.4(5) . . ? C10 C9 C8 118.6(5) . . ? C10 C9 H9A 120.7 . . ? C8 C9 H9A 120.7 . . ? C11 C10 C9 120.5(5) . . ? C11 C10 H10A 119.7 . . ? C9 C10 H10A 119.7 . . ? C12 C11 C10 119.3(5) . . ? C12 C11 H11A 120.4 . . ? C10 C11 H11A 120.4 . . ? N2 C12 C11 120.9(5) . . ? N2 C12 H12A 119.6 . . ? C11 C12 H12A 119.6 . . ? C12 N2 C8 120.5(4) . . ? C12 N2 Se1 128.2(4) . . ? C8 N2 Se1 111.2(3) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.33 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.866 _refine_diff_density_min -0.447 _refine_diff_density_rms 0.089