# Copyright The Royal Society of Chemistry, 1999 # CCDC Number: 207/331 data_default # 1. SUBMISSION DETAILS _publ_contact_author_name 'J. C. Jochims' _publ_contact_author_address ; Fakult\"at f\"ur Chemie Universit\"at Konstanz Postfach 78457 78434 Konstanz Bundesrepublik Deutschland ; _publ_contact_author_phone '049 7531 882687' _publ_contact_author_email johannes.jochims@uni-konstanz.de _publ_requested_journal ; Perkin Trans.1 ; _publ_requested_coeditor_name . _publ_contact_letter ; ; #======================================================================= # 3. TITLE AND AUTHOR LIST _publ_section_title ; Cycloadditions of 1-aza-2-azoniaallene cations to isothiocyanates ; loop_ _publ_author_name _publ_author_address 'A.-R. B. A. El-Gazzard' ; Fakult\"at f\"ur Chemie Universit\"at Konstanz Postfach 78457 78434 Konstanz Bundesrepublik Deutschland ; 'K. Scholten' ; Fakult\"at f\"ur Chemie Universit\"at Konstanz postfach 78457 78434 Konstanz Bundesrepublik Deutschland ; 'Y. Guo' ; Fakult\"at f\"ur Chemie Universit\"at Konstanz Postfach 78457 78434 Konstanz Bundesrepublik Deutschland ; 'K. Weissenbach' ; Fakult\"at f\"ur Chemie Universit\"at Konstanz Fach M 727 78457 Konstanz Bundesrepublik Deutschland ; 'M. G. Hitzler' ; Fakult\"at f\"ur Chemie Universit\"at Konstanz Postfach 78457 78434 Konstanz Bundesrepublik Deutschland ; 'G. Roth' ; Fakult\"at f\"ur Chemie Universit\"at Konstanz Fach M 727 78457 Konstanz Bundesrepublik Deutschland ; 'Fischer, Helmut' ; Fakult\"at f\"ur Chemie Universit\"at Konstanz Fach M 727 78457 Konstanz Bundesrepublik Deutschland ; 'Johannes C. Jochims' ; Fakult\"at f\"ur Chemie Universit\"at Konstanz Postfach 78457 78434 Konstanz Bundesrepublik Deutschland ; #======================================================================= # 4. TEXT _publ_section_abstract ; ; _publ_section_comment ; ; _publ_section_experimental ; ; _publ_section_references ; ; _publ_section_figure_captions ; ; _publ_section_acknowledgements ; ; data_sand _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety 'C18 H17 Cl3 N3 S +, Sb Cl6 -' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C18 H17 Cl9 N3 S Sb' _chemical_formula_weight 748.21 _chemical_melting_point ? _chemical_compound_source ? 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' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Sb' 'Sb' -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/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 8.114(11) _cell_length_b 26.501(11) _cell_length_c 13.450(6) _cell_angle_alpha 90.00 _cell_angle_beta 101.42(6) _cell_angle_gamma 90.00 _cell_volume 2835.0(43) _cell_formula_units_Z 4 _cell_measurement_temperature 248 _cell_measurement_reflns_used 26 _cell_measurement_theta_min 7.11 _cell_measurement_theta_max 12.95 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.753 _exptl_crystal_density_method ? _exptl_crystal_F_000 1464 _exptl_absorpt_coefficient_mu 1.909 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min . _exptl_absorpt_correction_T_max . _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Siemens P4' _diffrn_measurement_method '\w scans' _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6621 _diffrn_reflns_av_R_equivalents 0.0253 _diffrn_reflns_av_sigmaI/netI 0.0311 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min -33 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.18 _diffrn_reflns_theta_max 27.00 _reflns_number_total 6194 _reflns_number_observed 5218 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens SHELXTL' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens SHELXTL' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 1 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R- factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0340P)^2^+5.6604P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6193 _refine_ls_number_parameters 357 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0475 _refine_ls_R_factor_obs 0.0380 _refine_ls_wR_factor_all 0.0973 _refine_ls_wR_factor_obs 0.0904 _refine_ls_goodness_of_fit_all 1.048 _refine_ls_goodness_of_fit_obs 1.067 _refine_ls_restrained_S_all 1.049 _refine_ls_restrained_S_obs 1.067 _refine_ls_shift/esd_max -0.002 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group S1 S 0.74908(14) 0.35761(4) 0.43533(7) 0.0435(2) Uani 1 d . . C1 C 0.8862(5) 0.33075(15) 0.3673(3) 0.0420(8) Uani 1 d . . C2 C 1.0165(8) 0.2933(3) 0.4183(5) 0.067(2) Uani 1 d . . H2A H 1.0313(82) 0.2999(26) 0.4717(49) 0.085(23) Uiso 1 d . . H2B H 1.1237(75) 0.2979(22) 0.3919(43) 0.083(18) Uiso 1 d . . H2C H 0.9392(106) 0.2562(35) 0.4236(64) 0.154(32) Uiso 1 d . . N1 N 0.8566(4) 0.34242(11) 0.2711(2) 0.0359(6) Uani 1 d . . C3 C 0.9386(5) 0.3214(2) 0.1870(3) 0.0416(9) Uani 1 d . . H3A H 0.8817(50) 0.3407(15) 0.1263(31) 0.038(11) Uiso 1 d . . C4 C 0.8886(8) 0.2662(2) 0.1676(5) 0.0597(12) Uani 1 d . . H4B H 0.7653(75) 0.2626(21) 0.1493(40) 0.074(17) Uiso 1 d . . H4A H 0.9447(76) 0.2475(24) 0.2220(47) 0.087(20) Uiso 1 d . . H4C H 0.9401(79) 0.2555(24) 0.1082(49) 0.098(21) Uiso 1 d . . C5 C 1.1265(6) 0.3317(3) 0.2076(5) 0.0641(14) Uani 1 d . . H5A H 1.1914(76) 0.3081(24) 0.2606(47) 0.089(19) Uiso 1 d . . H5B H 1.1656(66) 0.3234(20) 0.1459(41) 0.069(15) Uiso 1 d . . H5C H 1.1429(68) 0.3637(23) 0.2355(41) 0.073(18) Uiso 1 d . . N2 N 0.7130(4) 0.37289(11) 0.2412(2) 0.0328(6) Uani 1 d . . C6 C 0.7022(4) 0.40532(12) 0.1543(3) 0.0308(7) Uani 1 d . . C7 C 0.8016(5) 0.44919(13) 0.1592(3) 0.0368(8) Uani 1 d . . Cl1 Cl 0.94211(15) 0.46265(4) 0.27173(9) 0.0570(3) Uani 1 d . . C8 C 0.7929(6) 0.48068(14) 0.0755(3) 0.0443(9) Uani 1 d . . H8A H 0.8642(59) 0.5090(18) 0.0832(35) 0.056(13) Uiso 1 d . . C9 C 0.6812(5) 0.46780(14) -0.0136(3) 0.0424(9) Uani 1 d . . Cl2 Cl 0.6715(2) 0.50637(4) -0.11946(9) 0.0661(4) Uani 1 d . . C10 C 0.5789(5) 0.4252(2) -0.0216(3) 0.0412(8) Uani 1 d . . H10A H 0.5054(56) 0.4146(17) -0.0820(35) 0.051(12) Uiso 1 d . . C11 C 0.5903(4) 0.39386(13) 0.0631(3) 0.0332(7) Uani 1 d . . Cl3 Cl 0.46832(13) 0.34016(4) 0.05643(8) 0.0494(2) Uani 1 d . . C12 C 0.6333(5) 0.38647(13) 0.3217(3) 0.0339(7) Uani 1 d . . N3 N 0.5065(4) 0.41483(13) 0.3082(2) 0.0410(7) Uani 1 d . . C13 C 0.4173(5) 0.4256(2) 0.3878(3) 0.0410(8) Uani 1 d . . C14 C 0.3551(5) 0.4744(2) 0.3948(3) 0.0473(10) Uani 1 d . . H14A H 0.3839(59) 0.4976(18) 0.3500(36) 0.054(13) Uiso 1 d . . C15 C 0.2624(6) 0.4861(2) 0.4684(4) 0.0596(13) Uani 1 d . . H15A H 0.2211(69) 0.5185(22) 0.4718(41) 0.076(17) Uiso 1 d . . C16 C 0.2322(7) 0.4492(3) 0.5361(4) 0.074(2) Uani 1 d . . H16A H 0.1680(69) 0.4568(21) 0.5881(42) 0.078(17) Uiso 1 d . . C17 C 0.2912(9) 0.4001(3) 0.5288(5) 0.084(2) Uani 1 d . . H17A H 0.2850(75) 0.3767(24) 0.5764(46) 0.089(20) Uiso 1 d . . C18 C 0.3828(7) 0.3880(2) 0.4544(4) 0.0658(14) Uani 1 d . . H18A H 0.4262(68) 0.3563(22) 0.4492(40) 0.072(16) Uiso 1 d . . Sb1 Sb -0.03611(3) 0.336345(9) -0.18869(2) 0.03561(8) Uani 1 d . . Cl4 Cl 0.0759(3) 0.26586(5) -0.08679(12) 0.0923(5) Uani 1 d . . Cl5 Cl 0.2364(2) 0.35078(7) -0.22279(11) 0.0792(4) Uani 1 d . . Cl6 Cl -0.1416(3) 0.40584(5) -0.29149(11) 0.0926(6) Uani 1 d . . Cl7 Cl -0.3019(2) 0.32079(6) -0.1495(2) 0.0978(6) Uani 1 d . . Cl8 Cl -0.1035(2) 0.28166(5) -0.33275(10) 0.0665(3) Uani 1 d . . Cl9 Cl 0.02846(14) 0.39005(4) -0.04410(8) 0.0489(2) 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 S1 0.0553(6) 0.0450(5) 0.0315(4) 0.0073(4) 0.0119(4) 0.0059(4) C1 0.045(2) 0.040(2) 0.042(2) 0.010(2) 0.011(2) 0.004(2) C2 0.067(3) 0.083(4) 0.054(3) 0.033(3) 0.020(3) 0.030(3) N1 0.036(2) 0.035(2) 0.037(2) 0.0081(12) 0.0095(12) 0.0057(12) C3 0.042(2) 0.045(2) 0.042(2) 0.009(2) 0.018(2) 0.012(2) C4 0.071(3) 0.042(2) 0.070(3) -0.001(2) 0.023(3) 0.011(2) C5 0.044(3) 0.086(4) 0.069(3) 0.006(3) 0.027(2) 0.007(3) N2 0.037(2) 0.0326(14) 0.0308(14) 0.0057(12) 0.0106(12) 0.0060(12) C6 0.035(2) 0.027(2) 0.032(2) 0.0049(13) 0.0109(14) 0.0043(13) C7 0.044(2) 0.031(2) 0.036(2) -0.0017(14) 0.011(2) 0.0012(15) Cl1 0.0646(7) 0.0503(6) 0.0508(6) -0.0075(5) -0.0014(5) -0.0165(5) C8 0.058(2) 0.027(2) 0.053(2) 0.004(2) 0.025(2) 0.001(2) C9 0.058(2) 0.036(2) 0.040(2) 0.011(2) 0.024(2) 0.016(2) Cl2 0.1066(10) 0.0525(6) 0.0478(6) 0.0231(5) 0.0365(6) 0.0273(6) C10 0.043(2) 0.050(2) 0.031(2) 0.000(2) 0.007(2) 0.014(2) C11 0.032(2) 0.032(2) 0.036(2) -0.0021(14) 0.0088(14) 0.0020(14) Cl3 0.0408(5) 0.0519(6) 0.0553(6) -0.0059(5) 0.0093(4) -0.0131(4) C12 0.040(2) 0.031(2) 0.032(2) 0.0016(13) 0.0115(14) -0.0045(14) N3 0.045(2) 0.044(2) 0.037(2) 0.0016(13) 0.0165(14) 0.0057(14) C13 0.040(2) 0.050(2) 0.035(2) -0.005(2) 0.012(2) 0.003(2) C14 0.039(2) 0.059(3) 0.043(2) -0.007(2) 0.007(2) 0.008(2) C15 0.046(2) 0.076(3) 0.057(3) -0.022(3) 0.012(2) 0.013(2) C16 0.069(3) 0.106(5) 0.055(3) -0.015(3) 0.031(3) 0.006(3) C17 0.105(5) 0.090(4) 0.074(4) 0.013(3) 0.059(4) 0.010(4) C18 0.079(4) 0.062(3) 0.069(3) 0.011(3) 0.044(3) 0.011(3) Sb1 0.04230(14) 0.02826(12) 0.03912(14) -0.00156(9) 0.01495(10) -0.00037(10) Cl4 0.153(2) 0.0493(7) 0.0780(9) 0.0214(7) 0.0305(10) 0.0366(9) Cl5 0.0578(7) 0.1141(12) 0.0752(8) -0.0257(8) 0.0359(6) -0.0235(7) Cl6 0.145(2) 0.0508(7) 0.0657(8) 0.0080(6) -0.0179(9) 0.0228(8) Cl7 0.0665(8) 0.0907(10) 0.155(2) -0.0673(11) 0.0664(10) -0.0392(8) Cl8 0.0859(9) 0.0557(7) 0.0610(7) -0.0256(6) 0.0220(6) -0.0105(6) Cl9 0.0601(6) 0.0447(5) 0.0436(5) -0.0083(4) 0.0142(4) -0.0046(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 C1 1.727(4) . ? S1 C12 1.799(4) . ? C1 N1 1.306(5) . ? C1 C2 1.512(6) . ? N1 N2 1.409(4) . ? N1 C3 1.527(5) . ? C3 C5 1.520(7) . ? C3 C4 1.528(6) . ? N2 C12 1.413(4) . ? N2 C6 1.440(4) . ? C6 C11 1.407(5) . ? C6 C7 1.409(5) . ? C7 C8 1.392(5) . ? C7 Cl1 1.742(4) . ? C8 C9 1.395(6) . ? C9 C10 1.393(6) . ? C9 Cl2 1.741(4) . ? C10 C11 1.397(5) . ? C11 Cl3 1.726(4) . ? C12 N3 1.258(5) . ? N3 C13 1.435(5) . ? C13 C14 1.398(6) . ? C13 C18 1.405(6) . ? C14 C15 1.391(6) . ? C15 C16 1.390(8) . ? C16 C17 1.397(9) . ? C17 C18 1.396(7) . ? Sb1 Cl7 2.356(3) . ? Sb1 Cl6 2.360(2) . ? Sb1 Cl5 2.376(3) . ? Sb1 Cl9 2.3829(13) . ? Sb1 Cl4 2.388(2) . ? Sb1 Cl8 2.3946(14) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 S1 C12 90.5(2) . . ? N1 C1 C2 125.4(4) . . ? N1 C1 S1 114.6(3) . . ? C2 C1 S1 119.8(3) . . ? C1 N1 N2 113.5(3) . . ? C1 N1 C3 128.8(3) . . ? N2 N1 C3 117.0(3) . . ? C5 C3 N1 111.6(4) . . ? C5 C3 C4 115.2(4) . . ? N1 C3 C4 109.6(3) . . ? N1 N2 C12 113.9(3) . . ? N1 N2 C6 119.2(3) . . ? C12 N2 C6 120.4(3) . . ? C11 C6 C7 118.9(3) . . ? C11 C6 N2 120.3(3) . . ? C7 C6 N2 120.8(3) . . ? C8 C7 C6 121.3(4) . . ? C8 C7 Cl1 120.0(3) . . ? C6 C7 Cl1 118.7(3) . . ? C7 C8 C9 118.0(4) . . ? C10 C9 C8 122.7(3) . . ? C10 C9 Cl2 118.9(3) . . ? C8 C9 Cl2 118.4(3) . . ? C9 C10 C11 118.5(4) . . ? C10 C11 C6 120.6(3) . . ? C10 C11 Cl3 120.2(3) . . ? C6 C11 Cl3 119.2(3) . . ? N3 C12 N2 121.8(3) . . ? N3 C12 S1 130.6(3) . . ? N2 C12 S1 107.6(3) . . ? C12 N3 C13 122.0(3) . . ? C14 C13 C18 119.5(4) . . ? C14 C13 N3 118.4(4) . . ? C18 C13 N3 122.0(4) . . ? C15 C14 C13 120.6(5) . . ? C16 C15 C14 119.9(5) . . ? C15 C16 C17 120.1(5) . . ? C18 C17 C16 120.2(6) . . ? C17 C18 C13 119.7(5) . . ? Cl7 Sb1 Cl6 91.47(9) . . ? Cl7 Sb1 Cl5 178.03(7) . . ? Cl6 Sb1 Cl5 90.27(9) . . ? Cl7 Sb1 Cl9 89.14(6) . . ? Cl6 Sb1 Cl9 90.44(6) . . ? Cl5 Sb1 Cl9 89.93(6) . . ? Cl7 Sb1 Cl4 89.77(9) . . ? Cl6 Sb1 Cl4 178.65(7) . . ? Cl5 Sb1 Cl4 88.49(9) . . ? Cl9 Sb1 Cl4 90.09(6) . . ? Cl7 Sb1 Cl8 90.15(7) . . ? Cl6 Sb1 Cl8 89.99(6) . . ? Cl5 Sb1 Cl8 90.77(7) . . ? Cl9 Sb1 Cl8 179.17(4) . . ? Cl4 Sb1 Cl8 89.49(7) . . ? 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 C12 S1 C1 N1 1.9(3) . . . . ? C12 S1 C1 C2 -172.8(4) . . . . ? C2 C1 N1 N2 171.6(5) . . . . ? S1 C1 N1 N2 -2.8(4) . . . . ? C2 C1 N1 C3 1.7(7) . . . . ? S1 C1 N1 C3 -172.7(3) . . . . ? C1 N1 C3 C5 -61.1(6) . . . . ? N2 N1 C3 C5 129.4(4) . . . . ? C1 N1 C3 C4 67.8(5) . . . . ? N2 N1 C3 C4 -101.8(4) . . . . ? C1 N1 N2 C12 2.4(4) . . . . ? C3 N1 N2 C12 173.5(3) . . . . ? C1 N1 N2 C6 154.3(3) . . . . ? C3 N1 N2 C6 -34.6(4) . . . . ? N1 N2 C6 C11 108.1(4) . . . . ? C12 N2 C6 C11 -101.9(4) . . . . ? N1 N2 C6 C7 -72.6(4) . . . . ? C12 N2 C6 C7 77.5(4) . . . . ? C11 C6 C7 C8 -1.0(5) . . . . ? N2 C6 C7 C8 179.6(3) . . . . ? C11 C6 C7 Cl1 -179.1(3) . . . . ? N2 C6 C7 Cl1 1.6(5) . . . . ? C6 C7 C8 C9 0.6(6) . . . . ? Cl1 C7 C8 C9 178.6(3) . . . . ? C7 C8 C9 C10 0.3(6) . . . . ? C7 C8 C9 Cl2 -179.0(3) . . . . ? C8 C9 C10 C11 -0.7(6) . . . . ? Cl2 C9 C10 C11 178.6(3) . . . . ? C9 C10 C11 C6 0.2(5) . . . . ? C9 C10 C11 Cl3 -179.1(3) . . . . ? C7 C6 C11 C10 0.6(5) . . . . ? N2 C6 C11 C10 179.9(3) . . . . ? C7 C6 C11 Cl3 179.9(3) . . . . ? N2 C6 C11 Cl3 -0.7(4) . . . . ? N1 N2 C12 N3 177.8(3) . . . . ? C6 N2 C12 N3 26.2(5) . . . . ? N1 N2 C12 S1 -0.9(3) . . . . ? C6 N2 C12 S1 -152.5(3) . . . . ? C1 S1 C12 N3 -179.0(4) . . . . ? C1 S1 C12 N2 -0.5(3) . . . . ? N2 C12 N3 C13 175.1(3) . . . . ? S1 C12 N3 C13 -6.6(6) . . . . ? C12 N3 C13 C14 141.9(4) . . . . ? C12 N3 C13 C18 -41.9(6) . . . . ? C18 C13 C14 C15 1.3(7) . . . . ? N3 C13 C14 C15 177.6(4) . . . . ? C13 C14 C15 C16 0.5(7) . . . . ? C14 C15 C16 C17 -1.6(9) . . . . ? C15 C16 C17 C18 1.0(10) . . . . ? C16 C17 C18 C13 0.8(10) . . . . ? C14 C13 C18 C17 -1.9(8) . . . . ? N3 C13 C18 C17 -178.1(5) . . . . ? _refine_diff_density_max 0.868 _refine_diff_density_min -0.789 _refine_diff_density_rms 0.087