# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Richard Oakley' 'Alicea A. Leitch' 'Courtney E McKenzie' 'Robert W. Reed' 'John F. Richardson' 'Lenora D. Sawyer' _publ_contact_author_name 'Richard Oakley' _publ_contact_author_address ; Department of Chemistry University of Waterloo Waterloo Ontario N2L 3G1 CANADA ; _publ_contact_author_email OAKLEY@SCIBORG.UWATERLOO.CA _publ_requested_journal 'Chemical Communications' _publ_section_title ; Bimodal association of a bis-1,2,3-dithiazolyl radical ; # Attachment 'bpzet_dimers_final.cif' data_rto27rt _database_code_depnum_ccdc_archive 'CCDC 292072' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'alpha BPzEt dimer' _chemical_melting_point ? _chemical_formula_moiety 'C12 H10 N8 S8' _chemical_formula_sum 'C12 H10 N8 S8' _chemical_formula_weight 522.84 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n _symmetry_space_group_name_Hall -P2yn 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 9.332(2) _cell_length_b 7.4076(16) _cell_length_c 14.207(3) _cell_angle_alpha 90.00 _cell_angle_beta 100.594(3) _cell_angle_gamma 90.00 _cell_volume 965.4(4) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3966 _cell_measurement_theta_min 2.42 _cell_measurement_theta_max 27.53 _exptl_crystal_description block _exptl_crystal_colour amber _exptl_crystal_size_max 0.130 _exptl_crystal_size_mid 0.077 _exptl_crystal_size_min 0.061 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.798 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 532 _exptl_absorpt_coefficient_mu 0.944 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.815 _exptl_absorpt_correction_T_max 0.944 _exptl_absorpt_process_details 'SADABS (George Sheldrick)' _exptl_special_details ; Data were collected with a Bruker SMART APEX CCD-based diffractometer using /w-scans of width 0.3 deg. and 30s duration at a crystal-to-detector distance of 4.908 cm. Intensity decay over the course of the data collection was evaluated by recollecting the first 50 frames of data at the end of the experiment. No significant decay was noted. ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX' _diffrn_measurement_method /w-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% <0.1 _diffrn_reflns_number 8071 _diffrn_reflns_av_R_equivalents 0.0276 _diffrn_reflns_av_sigmaI/netI 0.0313 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.42 _diffrn_reflns_theta_max 28.17 _reflns_number_total 2203 _reflns_number_gt 1839 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART 5.625 (Bruker, 2001)' _computing_cell_refinement 'SAINT 6.22 (Bruker, 2001)' _computing_data_reduction 'SAINT 6.22 (Bruker, 2001)' _computing_structure_solution 'SHELXS-90 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL 6.12 (Bruker, 2001)' _computing_publication_material 'SHELXTL 6.12 (Bruker, 2001)' _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^)+(0.0516P)^2^+0.4550P] 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 2203 _refine_ls_number_parameters 128 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0492 _refine_ls_R_factor_gt 0.0382 _refine_ls_wR_factor_ref 0.0949 _refine_ls_wR_factor_gt 0.0899 _refine_ls_goodness_of_fit_ref 1.005 _refine_ls_restrained_S_all 1.005 _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 0.42295(7) 0.91639(9) 0.68107(5) 0.0469(2) Uani 1 1 d . . . S2 S 0.29298(7) 0.73095(9) 0.73535(4) 0.03681(18) Uani 1 1 d . . . S3 S 0.06912(6) 0.20638(7) 0.51606(4) 0.03095(16) Uani 1 1 d . . . S4 S 0.10734(7) 0.18812(9) 0.37642(5) 0.0425(2) Uani 1 1 d . . . N1 N 0.2516(2) 0.6580(3) 0.45545(13) 0.0287(4) Uani 1 1 d . . . N2 N 0.3804(2) 0.8585(3) 0.56697(16) 0.0415(5) Uani 1 1 d . . . N3 N 0.13484(17) 0.5080(2) 0.61333(11) 0.0223(4) Uani 1 1 d . . . N4 N 0.1934(2) 0.3874(3) 0.37629(14) 0.0365(5) Uani 1 1 d . . . C1 C 0.2900(2) 0.7263(3) 0.54736(16) 0.0280(5) Uani 1 1 d . . . C2 C 0.2286(2) 0.6376(3) 0.62336(14) 0.0235(4) Uani 1 1 d . . . C3 C 0.0787(2) 0.4539(3) 0.51610(14) 0.0209(4) Uani 1 1 d . . . C4 C 0.1773(2) 0.4952(3) 0.44363(14) 0.0256(4) Uani 1 1 d . . . C5 C 0.3282(3) 0.7237(4) 0.37998(18) 0.0384(6) Uani 1 1 d . . . H5A H 0.3380 0.8538 0.3849 0.046 Uiso 1 1 calc R . . H5B H 0.2702 0.6958 0.3178 0.046 Uiso 1 1 calc R . . C6 C 0.4778(3) 0.6400(4) 0.3872(2) 0.0499(7) Uani 1 1 d . . . H6A H 0.5370 0.6713 0.4476 0.075 Uiso 1 1 calc R . . H6B H 0.5227 0.6845 0.3362 0.075 Uiso 1 1 calc R . . H6C H 0.4687 0.5111 0.3824 0.075 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0448(4) 0.0377(4) 0.0556(4) -0.0104(3) 0.0026(3) -0.0178(3) S2 0.0399(3) 0.0403(4) 0.0278(3) -0.0108(3) 0.0000(2) -0.0100(3) S3 0.0383(3) 0.0199(3) 0.0331(3) -0.0032(2) 0.0024(2) 0.0025(2) S4 0.0486(4) 0.0410(4) 0.0375(4) -0.0195(3) 0.0068(3) 0.0046(3) N1 0.0294(10) 0.0335(10) 0.0254(9) 0.0041(8) 0.0112(8) -0.0011(8) N2 0.0415(12) 0.0353(11) 0.0494(14) -0.0013(10) 0.0123(10) -0.0108(9) N3 0.0243(9) 0.0238(9) 0.0174(8) -0.0009(7) 0.0006(7) -0.0007(7) N4 0.0377(11) 0.0450(12) 0.0285(10) -0.0081(9) 0.0106(9) 0.0039(9) C1 0.0248(11) 0.0263(11) 0.0339(12) 0.0009(9) 0.0077(9) -0.0001(8) C2 0.0254(11) 0.0240(10) 0.0198(10) -0.0018(8) 0.0006(8) 0.0028(8) C3 0.0237(10) 0.0197(9) 0.0185(9) -0.0003(8) 0.0018(8) -0.0004(8) C4 0.0239(10) 0.0321(11) 0.0206(10) 0.0010(9) 0.0035(8) 0.0052(8) C5 0.0392(14) 0.0442(14) 0.0350(13) 0.0151(11) 0.0156(11) 0.0040(11) C6 0.0413(15) 0.0620(18) 0.0533(17) 0.0181(14) 0.0267(13) 0.0100(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 N2 1.653(2) . no S1 S2 2.0728(10) . no S1 N3 3.1404(18) 2_556 no S1 S2 3.4322(11) 2_556 no S2 C2 1.738(2) . no S2 N3 2.9587(18) 2_556 no S2 S3 3.5343(11) 2_556 no S3 C3 1.836(2) . no S3 S4 2.0837(10) . no S4 N4 1.681(2) . no N1 C1 1.385(3) . no N1 C4 1.386(3) . no N1 C5 1.476(3) . no N2 C1 1.289(3) . no N3 C2 1.289(3) . no N3 C3 1.441(2) . no N4 C4 1.276(3) . no C1 C2 1.468(3) . no C3 C4 1.533(3) . no C3 C3 1.607(4) 3_566 no C5 C6 1.514(3) . no C5 H5A 0.9700 . no C5 H5B 0.9700 . no C6 H6A 0.9600 . no C6 H6B 0.9600 . no C6 H6C 0.9600 . no 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 S2 98.12(8) . . no C2 S2 S1 92.91(8) . . no C3 S3 S4 92.77(7) . . no N4 S4 S3 96.29(7) . . no C1 N1 C4 117.99(18) . . no C1 N1 C5 119.3(2) . . no C4 N1 C5 119.81(19) . . no C1 N2 S1 116.02(18) . . no C2 N3 C3 115.64(17) . . no C4 N4 S4 115.24(17) . . no N2 C1 N1 121.8(2) . . no N2 C1 C2 120.7(2) . . no N1 C1 C2 117.50(19) . . no N3 C2 C1 126.96(19) . . no N3 C2 S2 120.75(16) . . no C1 C2 S2 112.28(16) . . no N3 C3 C4 115.53(16) . . no N3 C3 C3 107.89(19) . 3_566 no C4 C3 C3 110.74(19) . 3_566 no N3 C3 S3 106.66(13) . . no C4 C3 S3 103.54(13) . . no C3 C3 S3 112.48(17) 3_566 . no N4 C4 N1 120.65(19) . . no N4 C4 C3 123.2(2) . . no N1 C4 C3 116.18(17) . . no N1 C5 C6 112.3(2) . . no N1 C5 H5A 109.1 . . no C6 C5 H5A 109.1 . . no N1 C5 H5B 109.1 . . no C6 C5 H5B 109.1 . . no H5A C5 H5B 107.9 . . no C5 C6 H6A 109.5 . . no C5 C6 H6B 109.5 . . no H6A C6 H6B 109.5 . . no C5 C6 H6C 109.5 . . no H6A C6 H6C 109.5 . . no H6B C6 H6C 109.5 . . no 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 N2 S1 S2 C2 0.72(11) . . . . no C3 S3 S4 N4 24.18(10) . . . . no S2 S1 N2 C1 -1.0(2) . . . . no S3 S4 N4 C4 -15.69(18) . . . . no S1 N2 C1 N1 -176.35(17) . . . . no S1 N2 C1 C2 1.0(3) . . . . no C4 N1 C1 N2 167.6(2) . . . . no C5 N1 C1 N2 7.0(3) . . . . no C4 N1 C1 C2 -9.8(3) . . . . no C5 N1 C1 C2 -170.41(19) . . . . no C3 N3 C2 C1 -4.2(3) . . . . no C3 N3 C2 S2 174.01(14) . . . . no N2 C1 C2 N3 178.1(2) . . . . no N1 C1 C2 N3 -4.5(3) . . . . no N2 C1 C2 S2 -0.3(3) . . . . no N1 C1 C2 S2 177.15(15) . . . . no S1 S2 C2 N3 -178.82(17) . . . . no S1 S2 C2 C1 -0.36(15) . . . . no C2 N3 C3 C4 24.6(2) . . . . no C2 N3 C3 C3 -99.9(2) . . . 3_566 no C2 N3 C3 S3 138.99(16) . . . . no S4 S3 C3 N3 -149.09(12) . . . . no S4 S3 C3 C4 -26.77(12) . . . . no S4 S3 C3 C3 92.82(18) . . . 3_566 no S4 N4 C4 N1 175.13(15) . . . . no S4 N4 C4 C3 -4.0(3) . . . . no C1 N1 C4 N4 -148.9(2) . . . . no C5 N1 C4 N4 11.5(3) . . . . no C1 N1 C4 C3 30.3(3) . . . . no C5 N1 C4 C3 -169.29(18) . . . . no N3 C3 C4 N4 140.7(2) . . . . no C3 C3 C4 N4 -96.3(3) 3_566 . . . no S3 C3 C4 N4 24.5(2) . . . . no N3 C3 C4 N1 -38.5(2) . . . . no C3 C3 C4 N1 84.5(2) 3_566 . . . no S3 C3 C4 N1 -154.72(15) . . . . no C1 N1 C5 C6 77.5(3) . . . . no C4 N1 C5 C6 -82.7(3) . . . . no _diffrn_measured_fraction_theta_max 0.930 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 0.492 _refine_diff_density_min -0.372 _refine_diff_density_rms 0.071 data_rto26rt _database_code_depnum_ccdc_archive 'CCDC 292073' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'beta BPzEt dimer' _chemical_melting_point ? _chemical_formula_moiety 'C12 H10 N8 S8' _chemical_formula_sum 'C12 H10 N8 S8' _chemical_formula_weight 522.84 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall -P2ybc 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 4.5411(15) _cell_length_b 7.583(2) _cell_length_c 27.391(9) _cell_angle_alpha 90.00 _cell_angle_beta 94.050(5) _cell_angle_gamma 90.00 _cell_volume 940.9(5) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1770 _cell_measurement_theta_min 2.29 _cell_measurement_theta_max 25.65 _exptl_crystal_description plate _exptl_crystal_colour black _exptl_crystal_size_max 0.206 _exptl_crystal_size_mid 0.056 _exptl_crystal_size_min 0.023 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.845 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 532 _exptl_absorpt_coefficient_mu 0.969 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.73 _exptl_absorpt_correction_T_max 0.98 _exptl_absorpt_process_details 'SADABS (George Sheldrick)' _exptl_special_details ; Data were collected with a Bruker SMART APEX CCD-based diffractometer using /w-scans of width 0.3 deg. and 30s duration at a crystal-to-detector distance of 4.908 cm. Intensity decay over the course of the data collection was evaluated by recollecting the first 50 frames of data at the end of the experiment. No significant decay was noted. ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX' _diffrn_measurement_method /w-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% <0.1 _diffrn_reflns_number 7492 _diffrn_reflns_av_R_equivalents 0.0718 _diffrn_reflns_av_sigmaI/netI 0.0913 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 2.79 _diffrn_reflns_theta_max 27.74 _reflns_number_total 2000 _reflns_number_gt 1319 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART 5.625 (Bruker, 2001)' _computing_cell_refinement 'SAINT 6.22 (Bruker, 2001)' _computing_data_reduction 'SAINT 6.22 (Bruker, 2001)' _computing_structure_solution 'SHELXS-90 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL 6.12 (Bruker, 2001)' _computing_publication_material 'SHELXTL 6.12 (Bruker, 2001)' _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^)+(0.0391P)^2^+6.3930P] 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 ? _refine_ls_number_reflns 2000 _refine_ls_number_parameters 128 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1229 _refine_ls_R_factor_gt 0.0782 _refine_ls_wR_factor_ref 0.1847 _refine_ls_wR_factor_gt 0.1725 _refine_ls_goodness_of_fit_ref 1.196 _refine_ls_restrained_S_all 1.196 _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 S1 S -0.3567(4) 0.9535(3) 0.21319(7) 0.0324(5) Uani 1 1 d . . . S2 S -0.0870(5) 0.7606(3) 0.24607(7) 0.0315(5) Uani 1 1 d . . . S3 S 0.5263(5) 0.3474(3) 0.13606(7) 0.0361(6) Uani 1 1 d . . . S4 S 0.5131(4) 0.4467(3) 0.03682(7) 0.0303(5) Uani 1 1 d . . . N1 N -0.0112(13) 0.7472(8) 0.1048(2) 0.0269(14) Uani 1 1 d . . . N2 N -0.2961(14) 0.9123(8) 0.1560(2) 0.0319(15) Uani 1 1 d . . . N3 N 0.2198(14) 0.5634(8) 0.1878(2) 0.0282(14) Uani 1 1 d . . . N4 N 0.2784(13) 0.5949(8) 0.0548(2) 0.0272(14) Uani 1 1 d . . . C1 C -0.1007(15) 0.7886(9) 0.1495(3) 0.0234(16) Uani 1 1 d . . . C2 C 0.0323(16) 0.6911(9) 0.1906(3) 0.0240(16) Uani 1 1 d . . . C3 C 0.3015(15) 0.5144(9) 0.1420(3) 0.0245(16) Uani 1 1 d . . . C4 C 0.1958(15) 0.6139(10) 0.0990(3) 0.0258(16) Uani 1 1 d . . . C5 C -0.1261(17) 0.8581(10) 0.0638(3) 0.0306(17) Uani 1 1 d . . . H5A H -0.3362 0.8759 0.0661 0.037 Uiso 1 1 calc R . . H5B H -0.0992 0.7974 0.0333 0.037 Uiso 1 1 calc R . . C6 C 0.025(2) 1.0345(10) 0.0632(3) 0.043(2) Uani 1 1 d . . . H6A H 0.0177 1.0896 0.0947 0.064 Uiso 1 1 calc R . . H6B H -0.0735 1.1080 0.0386 0.064 Uiso 1 1 calc R . . H6C H 0.2270 1.0186 0.0560 0.064 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0365(11) 0.0302(10) 0.0318(11) -0.0049(9) 0.0118(8) 0.0051(9) S2 0.0428(12) 0.0304(10) 0.0228(10) -0.0013(8) 0.0124(8) 0.0036(9) S3 0.0484(13) 0.0300(10) 0.0306(11) 0.0000(9) 0.0069(9) 0.0142(10) S4 0.0381(11) 0.0282(10) 0.0256(10) -0.0035(8) 0.0095(8) 0.0035(9) N1 0.036(4) 0.024(3) 0.022(3) 0.004(3) 0.005(3) 0.007(3) N2 0.041(4) 0.027(3) 0.028(3) -0.008(3) 0.005(3) 0.008(3) N3 0.039(4) 0.023(3) 0.023(3) 0.005(3) 0.008(3) 0.006(3) N4 0.035(4) 0.022(3) 0.025(3) -0.002(3) 0.009(3) -0.001(3) C1 0.027(4) 0.018(4) 0.025(4) -0.004(3) 0.001(3) -0.006(3) C2 0.030(4) 0.018(3) 0.024(4) -0.002(3) 0.009(3) -0.006(3) C3 0.027(4) 0.021(4) 0.026(4) -0.002(3) 0.004(3) -0.001(3) C4 0.022(4) 0.029(4) 0.026(4) -0.006(3) 0.002(3) -0.002(3) C5 0.037(4) 0.036(4) 0.019(4) 0.003(3) 0.001(3) 0.009(4) C6 0.057(6) 0.027(4) 0.046(5) 0.003(4) 0.011(4) 0.000(4) _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 N2 1.640(6) . no S1 S2 2.073(3) . no S2 C2 1.730(7) . no S2 S1 3.226(3) 2_545 no S3 C3 1.641(7) . no S4 N4 1.648(6) . no S4 S4 2.168(4) 3_665 no N1 C1 1.354(9) . no N1 C4 1.397(9) . no N1 C5 1.468(9) . no N2 C1 1.312(9) . no N3 C2 1.295(9) . no N3 C3 1.386(8) . no N3 S1 2.862(6) 2_545 no N3 S2 3.011(6) 2_545 no N4 C4 1.300(9) . no C1 C2 1.444(10) . no C3 C4 1.451(10) . no C5 C6 1.504(11) . no C5 H5A 0.9700 . no C5 H5B 0.9700 . no C6 H6A 0.9600 . no C6 H6B 0.9600 . no C6 H6C 0.9600 . no 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 S2 98.4(2) . . no C2 S2 S1 92.6(3) . . no N4 S4 S4 91.7(2) . 3_665 no C1 N1 C4 121.2(6) . . no C1 N1 C5 116.4(6) . . no C4 N1 C5 122.2(6) . . no C1 N2 S1 115.3(5) . . no C2 N3 C3 118.2(6) . . no C4 N4 S4 126.1(5) . . no N2 C1 N1 122.5(6) . . no N2 C1 C2 120.7(6) . . no N1 C1 C2 116.8(6) . . no N3 C2 C1 125.3(6) . . no N3 C2 S2 121.8(6) . . no C1 C2 S2 112.9(5) . . no N3 C3 C4 120.1(6) . . no N3 C3 S3 120.3(5) . . no C4 C3 S3 119.6(5) . . no N4 C4 N1 115.3(6) . . no N4 C4 C3 126.6(7) . . no N1 C4 C3 118.1(6) . . no N1 C5 C6 112.3(7) . . no N1 C5 H5A 109.1 . . no C6 C5 H5A 109.1 . . no N1 C5 H5B 109.1 . . no C6 C5 H5B 109.1 . . no H5A C5 H5B 107.9 . . no C5 C6 H6A 109.5 . . no C5 C6 H6B 109.5 . . no H6A C6 H6B 109.5 . . no C5 C6 H6C 109.5 . . no H6A C6 H6C 109.5 . . no H6B C6 H6C 109.5 . . no 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 N2 S1 S2 C2 2.2(3) . . . . no S2 S1 N2 C1 -3.5(6) . . . . no S4 S4 N4 C4 -177.0(6) 3_665 . . . no S1 N2 C1 N1 -175.4(5) . . . . no S1 N2 C1 C2 3.8(9) . . . . no C4 N1 C1 N2 -179.5(7) . . . . no C5 N1 C1 N2 4.8(10) . . . . no C4 N1 C1 C2 1.2(10) . . . . no C5 N1 C1 C2 -174.4(6) . . . . no C3 N3 C2 C1 -0.1(11) . . . . no C3 N3 C2 S2 179.3(5) . . . . no N2 C1 C2 N3 177.8(7) . . . . no N1 C1 C2 N3 -3.0(10) . . . . no N2 C1 C2 S2 -1.7(9) . . . . no N1 C1 C2 S2 177.6(5) . . . . no S1 S2 C2 N3 179.8(6) . . . . no S1 S2 C2 C1 -0.7(5) . . . . no C2 N3 C3 C4 4.8(10) . . . . no C2 N3 C3 S3 -177.1(6) . . . . no S4 N4 C4 N1 -178.7(5) . . . . no S4 N4 C4 C3 2.8(11) . . . . no C1 N1 C4 N4 -175.5(6) . . . . no C5 N1 C4 N4 -0.2(10) . . . . no C1 N1 C4 C3 3.1(10) . . . . no C5 N1 C4 C3 178.5(7) . . . . no N3 C3 C4 N4 172.2(7) . . . . no S3 C3 C4 N4 -5.9(10) . . . . no N3 C3 C4 N1 -6.3(10) . . . . NO S3 C3 C4 N1 175.6(5) . . . . NO C1 N1 C5 C6 76.1(8) . . . . NO C4 N1 C5 C6 -99.5(8) . . . . NO _diffrn_measured_fraction_theta_max 0.907 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.626 _refine_diff_density_min -0.480 _refine_diff_density_rms 0.126