# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2002 #=============================================================================== data_global #=============================================================================== # 1. SUBMISSION DETAILS _journal_coden_Cambridge 182 _publ_contact_author_name 'Prof Richard Oakley' _publ_contact_author_address ; Department of Chemistry University of Waterloo Waterloo Ontario N2L 3G1 CANADA ; _publ_contact_author_phone '519-888-4582' _publ_contact_author_fax '519-746-0435' _publ_contact_author_email oakley@sciborg.uwaterloo.ca _publ_requested_journal 'Chemical Communications' _publ_requested_coeditor_name ? #============================================================================== # 2. TITLE AND AUTHOR LIST _publ_section_title ; A pi-stacked 1,2,3-dithiazolyl radical. Preparation and solid state characterization of (Cl2C2NS)(ClC2NS2) ; loop_ _publ_author_name _publ_author_address 'Beer, L.' ; Department of Chemistry University of Waterloo Waterloo, Ontario N2L 3G1 Canada ; 'Cordes, A.W.' ; Department of Chemistry and Biochemistry University of Arkansas Fayetteville, Arkansas 72701 USA ; 'Haddon, R.C.' ; Department of Chemistry University of California Riverside, California 92521 0403 USA ; 'Itkis, M.E.' ; Department of Chemistry University of California Riverside, California 92521 0403 USA ; 'Oakley, R.T.' ; Department of Chemistry University of Waterloo Waterloo, Ontario N2L 3G1 Canada ; 'Reed, R.W.' ; Department of Chemistry University of Waterloo Waterloo, Ontario N2L 3G1 Canada ; 'Robertson, C.M.' ; Department of Chemistry University of Waterloo Waterloo, Ontario N2L 3G1 Canada ; #=============================================================================== data_cation #=============================================================================== _database_code_CSD 186279 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'Compound [4][GaCl4]' _chemical_formula_moiety ' [(Cl2C2NS)(ClC2NS2)][GaCL4]' _chemical_formula_sum 'C5 Cl7 Ga N2 S3' _chemical_formula_weight 502.12 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' 'Cl' 'Cl' 0.1484 0.1585 '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' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Ga' 'Ga' 0.2307 1.6083 '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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, z+1/2' '-x, -y, -z' '-x-1/2, y-1/2, -z-1/2' _cell_length_a 7.8222(8) _cell_length_b 14.0812(14) _cell_length_c 14.4301(15) _cell_angle_alpha 90.00 _cell_angle_beta 98.882(5) _cell_angle_gamma 90.00 _cell_volume 1570.4(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4491 _cell_measurement_theta_min 2 _cell_measurement_theta_max 26 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max .3 _exptl_crystal_size_mid .3 _exptl_crystal_size_min .3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.124 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 968 _exptl_absorpt_coefficient_mu 3.321 _exptl_absorpt_correction_type 'empirical, R.A.Jacobson, MS Corp, 1998' _exptl_absorpt_correction_T_min 0.79 _exptl_absorpt_correction_T_max 1.00 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Mercury CCD - AFC8S' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2908 _diffrn_reflns_av_R_equivalents 0.022 _diffrn_reflns_av_sigmaI/netI 0.024 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.89 _diffrn_reflns_theta_max 26.02 _reflns_number_total 2907 _reflns_number_gt 2552 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Corp, 1999)' _computing_cell_refinement 'CrystalClear (Rigaku Corp, 1999)' _computing_data_reduction 'Texsan (Molecular Structure Corp, 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep3,v1.05, L.J.Farrugia,UnivGlasgow' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. wR and GOF are based on F^2^, conventional R's are based on F. The expression F^2^>2sigma(F^2^) is used only for the R-factor(gt). R's based on F^2^ are about twice as large as those based on F and R's based on ALL data will be even larger ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens ? _refine_ls_hydrogen_treatment ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0070(17) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2907 _refine_ls_number_parameters 164 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0512 _refine_ls_R_factor_gt 0.0437 _refine_ls_wR_factor_ref 0.1695 _refine_ls_wR_factor_gt 0.1574 _refine_ls_goodness_of_fit_ref 1.355 _refine_ls_restrained_S_all 1.355 _refine_ls_shift/su_max 0.011 _refine_ls_shift/su_mean 0.002 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ga Ga 0.15515(7) 0.73430(4) 0.41675(3) 0.0424(3) Uani 1 d . . . Cl2 Cl -0.43521(16) 0.58595(9) 0.58951(8) 0.0474(3) Uani 1 d . . . S1 S -0.08665(16) 0.66693(10) 0.66325(9) 0.0491(4) Uani 1 d . . . Cl4 Cl 0.06507(18) 0.74397(10) 0.26706(9) 0.0527(4) Uani 1 d . . . Cl6 Cl 0.11986(18) 0.58928(9) 0.45924(10) 0.0555(4) Uani 1 d . . . S2 S 0.16535(17) 0.70217(11) 0.70329(10) 0.0545(4) Uani 1 d . . . S3 S -0.25744(18) 0.44852(10) 0.84292(9) 0.0530(4) Uani 1 d . . . Cl1 Cl 0.1259(2) 0.48811(12) 0.88713(10) 0.0675(4) Uani 1 d . . . Cl3 Cl -0.70192(18) 0.43040(11) 0.65539(10) 0.0594(4) Uani 1 d . . . Cl7 Cl 0.4282(2) 0.77283(15) 0.44196(14) 0.0926(7) Uani 1 d . . . Cl8 Cl 0.0131(3) 0.82555(14) 0.49770(13) 0.0923(7) Uani 1 d . . . C3 C -0.2356(6) 0.5242(3) 0.7520(3) 0.0351(9) Uani 1 d . . . N2 N -0.4530(6) 0.4133(3) 0.7979(3) 0.0552(11) Uani 1 d . . . C2 C -0.0830(6) 0.5806(3) 0.7449(3) 0.0362(9) Uani 1 d . . . N1 N 0.2113(6) 0.6256(3) 0.7846(3) 0.0523(10) Uani 1 d . . . C1 C 0.0840(6) 0.5707(4) 0.7992(3) 0.0435(11) Uani 1 d . . . C5 C -0.5036(6) 0.4554(3) 0.7186(3) 0.0431(10) Uani 1 d . . . C4 C -0.3860(6) 0.5213(3) 0.6888(3) 0.0374(9) Uani 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 Ga 0.0474(4) 0.0418(4) 0.0380(4) 0.0047(2) 0.0065(3) -0.0038(2) Cl2 0.0522(7) 0.0519(7) 0.0347(6) 0.0061(5) -0.0045(5) -0.0055(5) S1 0.0436(7) 0.0523(8) 0.0495(8) 0.0136(6) 0.0018(5) -0.0043(5) Cl4 0.0535(8) 0.0673(8) 0.0377(7) 0.0069(5) 0.0079(5) 0.0056(6) Cl6 0.0613(8) 0.0429(7) 0.0623(8) 0.0120(6) 0.0092(6) -0.0064(5) S2 0.0438(7) 0.0583(8) 0.0606(8) 0.0019(7) 0.0058(6) -0.0073(6) S3 0.0665(9) 0.0527(8) 0.0382(7) 0.0110(5) 0.0032(6) -0.0050(6) Cl1 0.0637(9) 0.0731(10) 0.0588(9) 0.0185(7) -0.0122(7) 0.0079(7) Cl3 0.0527(7) 0.0634(9) 0.0610(9) -0.0046(6) 0.0051(6) -0.0180(6) Cl7 0.0584(10) 0.1135(16) 0.0969(13) 0.0516(11) -0.0161(8) -0.0360(9) Cl8 0.1471(19) 0.0746(12) 0.0609(10) -0.0117(8) 0.0339(11) 0.0304(11) C3 0.042(2) 0.037(2) 0.027(2) -0.0011(17) 0.0075(17) 0.0036(18) N2 0.064(3) 0.053(3) 0.049(3) 0.003(2) 0.008(2) -0.016(2) C2 0.042(2) 0.039(2) 0.027(2) -0.0035(17) 0.0040(17) 0.0065(18) N1 0.043(2) 0.053(3) 0.057(3) -0.004(2) -0.0032(19) -0.002(2) C1 0.046(3) 0.044(3) 0.039(2) -0.004(2) 0.002(2) 0.006(2) C5 0.054(3) 0.036(2) 0.039(3) -0.0041(19) 0.006(2) -0.008(2) C4 0.045(2) 0.037(2) 0.030(2) -0.0038(17) 0.0052(18) -0.0021(18) _geom_special_details ; ; 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 Ga Cl8 2.1567(17) . ? Ga Cl6 2.1621(14) . ? Ga Cl4 2.1704(14) . ? Ga Cl7 2.1790(17) . ? Cl2 C4 1.692(5) . ? S1 C2 1.689(5) . ? S1 S2 2.0283(19) . ? S2 N1 1.593(5) . ? S3 N2 1.643(5) . ? S3 C3 1.719(4) . ? Cl1 C1 1.716(5) . ? Cl3 C5 1.710(5) . ? C3 C4 1.373(6) . ? C3 C2 1.450(6) . ? N2 C5 1.295(6) . ? C2 C1 1.423(6) . ? N1 C1 1.303(7) . ? C5 C4 1.419(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 Cl8 Ga Cl6 108.06(7) . . ? Cl8 Ga Cl4 112.73(7) . . ? Cl6 Ga Cl4 107.79(6) . . ? Cl8 Ga Cl7 109.57(10) . . ? Cl6 Ga Cl7 110.64(7) . . ? Cl4 Ga Cl7 108.05(7) . . ? C2 S1 S2 93.81(17) . . ? N1 S2 S1 98.23(17) . . ? N2 S3 C3 94.7(2) . . ? C4 C3 C2 126.8(4) . . ? C4 C3 S3 108.2(3) . . ? C2 C3 S3 125.0(3) . . ? C5 N2 S3 110.5(3) . . ? C1 C2 C3 127.1(4) . . ? C1 C2 S1 111.7(4) . . ? C3 C2 S1 121.2(3) . . ? C1 N1 S2 115.4(4) . . ? N1 C1 C2 120.8(5) . . ? N1 C1 Cl1 117.3(4) . . ? C2 C1 Cl1 121.9(4) . . ? N2 C5 C4 116.2(4) . . ? N2 C5 Cl3 120.4(4) . . ? C4 C5 Cl3 123.4(4) . . ? C3 C4 C5 110.4(4) . . ? C3 C4 Cl2 127.3(4) . . ? C5 C4 Cl2 122.3(4) . . ? _diffrn_measured_fraction_theta_max 0.937 _diffrn_reflns_theta_full 26.02 _diffrn_measured_fraction_theta_full 0.937 _refine_diff_density_max 0.799 _refine_diff_density_min -0.647 _refine_diff_density_rms 0.105 #========================================================================== data_radical #========================================================================== _database_code_CSD 186280 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'A 1,2,3-dithiazolyl - Compound 4' _chemical_formula_moiety [(Cl2C2NS)(ClC2NS2)] _chemical_formula_sum 'C5 Cl3 N2 S3' _chemical_formula_weight 290.60 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' 'S' 'S' 0.1246 0.1234 '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' 'N' 'N' 0.0061 0.0033 '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' _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 3.8833(6) _cell_length_b 17.557(3) _cell_length_c 13.668(2) _cell_angle_alpha 90.00 _cell_angle_beta 93.428(9) _cell_angle_gamma 90.00 _cell_volume 930.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2246 _cell_measurement_theta_min 2 _cell_measurement_theta_max 26 _exptl_crystal_description needle _exptl_crystal_colour black _exptl_crystal_size_max 0.54 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.075 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 572 _exptl_absorpt_coefficient_mu 1.603 _exptl_absorpt_correction_type 'empirical, R.A.Jacobson, MS Corp, 1998' _exptl_absorpt_correction_T_min 0.76 _exptl_absorpt_correction_T_max 1.00 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Mercury CCD - AFC8S' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1738 _diffrn_reflns_av_R_equivalents 0.031 _diffrn_reflns_av_sigmaI/netI 0.043 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.32 _diffrn_reflns_theta_max 26.01 _reflns_number_total 1737 _reflns_number_gt 1324 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Corp, 1999)' _computing_cell_refinement 'CrystalClear (Rigaku Corp, 1999)' _computing_data_reduction 'Texsan (Molecular Structure Corp, 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep3,v1.05, L.J.Farrugia,UnivGlasgow' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. wR and GOF are based on F^2^, conventional R's are based on F. The expression F^2^>2sigma(F^2^) is used only for the R-factor(gt). R's based on F^2^ are about twice as large as those based on F and R's based on ALL data will be even larger ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0258P)^2^+2.958P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens ? _refine_ls_hydrogen_treatment ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1737 _refine_ls_number_parameters 118 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0679 _refine_ls_R_factor_gt 0.0457 _refine_ls_wR_factor_ref 0.1018 _refine_ls_wR_factor_gt 0.0938 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.066 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.5638(4) 0.85907(8) 0.45789(9) 0.0489(4) Uani 1 d . . . Cl2 Cl 0.9696(4) 0.96154(8) 0.62832(10) 0.0533(4) Uani 1 d . . . Cl3 Cl 0.5176(4) 0.58885(7) 0.70678(9) 0.0475(4) Uani 1 d . . . S1 S 0.2946(3) 0.69941(7) 0.43122(8) 0.0328(3) Uani 1 d . . . S2 S 0.1045(3) 0.58828(7) 0.42414(9) 0.0365(3) Uani 1 d . . . S3 S 0.7886(3) 0.74637(7) 0.72540(8) 0.0371(3) Uani 1 d . . . N1 N 0.2222(11) 0.5628(2) 0.5367(3) 0.0367(9) Uani 1 d . . . N2 N 0.9298(11) 0.8361(2) 0.7300(3) 0.0389(10) Uani 1 d . . . C1 C 0.3846(12) 0.6151(3) 0.5882(3) 0.0296(10) Uani 1 d . . . C2 C 0.4503(11) 0.6890(2) 0.5531(3) 0.0284(10) Uani 1 d . . . C3 C 0.6194(11) 0.7507(3) 0.6046(3) 0.0261(9) Uani 1 d . . . C4 C 0.6797(12) 0.8245(3) 0.5721(3) 0.0310(10) Uani 1 d . . . C5 C 0.8532(12) 0.8682(3) 0.6460(4) 0.0346(11) Uani 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 Cl1 0.0684(9) 0.0433(7) 0.0336(7) 0.0081(6) -0.0079(6) -0.0052(6) Cl2 0.0670(10) 0.0355(7) 0.0569(9) -0.0073(6) -0.0014(7) -0.0122(6) Cl3 0.0662(9) 0.0442(7) 0.0306(6) 0.0114(6) -0.0093(6) -0.0056(7) S1 0.0404(7) 0.0335(6) 0.0238(6) 0.0015(5) -0.0045(5) -0.0012(5) S2 0.0448(7) 0.0308(6) 0.0327(6) -0.0018(5) -0.0069(5) -0.0013(5) S3 0.0453(7) 0.0409(7) 0.0242(6) -0.0008(5) -0.0053(5) -0.0025(6) N1 0.044(2) 0.032(2) 0.034(2) -0.0004(17) -0.0056(19) -0.0005(18) N2 0.044(3) 0.039(2) 0.032(2) -0.0105(19) -0.0028(19) -0.002(2) C1 0.033(2) 0.033(2) 0.023(2) 0.0029(19) 0.0023(19) -0.003(2) C2 0.027(2) 0.033(2) 0.026(2) 0.0003(19) 0.0011(19) 0.0055(19) C3 0.026(2) 0.031(2) 0.022(2) -0.0019(18) 0.0008(17) 0.0027(18) C4 0.034(3) 0.033(2) 0.026(2) 0.000(2) 0.004(2) -0.002(2) C5 0.038(3) 0.031(2) 0.035(3) -0.007(2) 0.004(2) 0.000(2) _geom_special_details ; ; 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 Cl1 C4 1.710(5) . ? Cl2 C5 1.720(5) . ? Cl3 C1 1.733(4) . ? S1 C2 1.748(4) . ? S1 S2 2.0862(18) . ? S2 N1 1.641(4) . ? S3 N2 1.667(4) . ? S3 C3 1.742(4) . ? N1 C1 1.298(6) . ? N2 C5 1.298(6) . ? C1 C2 1.412(6) . ? C2 C3 1.430(6) . ? C3 C4 1.393(6) . ? C4 C5 1.407(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 C2 S1 S2 92.75(16) . . ? N1 S2 S1 97.69(15) . . ? N2 S3 C3 95.7(2) . . ? C1 N1 S2 114.5(3) . . ? C5 N2 S3 108.7(3) . . ? N1 C1 C2 123.9(4) . . ? N1 C1 Cl3 115.2(3) . . ? C2 C1 Cl3 120.8(3) . . ? C1 C2 C3 128.0(4) . . ? C1 C2 S1 111.1(3) . . ? C3 C2 S1 120.8(3) . . ? C4 C3 C2 129.0(4) . . ? C4 C3 S3 106.3(3) . . ? C2 C3 S3 124.7(3) . . ? C3 C4 C5 111.2(4) . . ? C3 C4 Cl1 125.5(4) . . ? C5 C4 Cl1 123.3(4) . . ? N2 C5 C4 118.1(4) . . ? N2 C5 Cl2 119.3(4) . . ? C4 C5 Cl2 122.5(4) . . ? _diffrn_measured_fraction_theta_max 0.944 _diffrn_reflns_theta_full 26.01 _diffrn_measured_fraction_theta_full 0.944 _refine_diff_density_max 0.379 _refine_diff_density_min -0.355 _refine_diff_density_rms 0.094 #=====================================================================