# 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 'Yunqi Liu' _publ_contact_author_email LIUYQ@MAIL.ICCAS.AC.CN _publ_section_title ; Synthesis and Properties of the anti and syn Isomers of Dibenzothieno[b,d]pyrrole ; loop_ _publ_author_name 'Yunqi Liu.' 'Chunyan Du.' 'Xike Gao.' 'Yunlong Guo.' 'Ying Liu.' 'Kun Lu.' ; Ting Qi ; 'Giu Yu.' 'Hengjun Zhang.' 'Daoben Zhu.' # Attachment '1-anti.cif' data_sx2341 _database_code_depnum_ccdc_archive 'CCDC 697266' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H9 N S2' _chemical_formula_sum 'C16 H9 N S2' _chemical_formula_weight 279.36 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 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 9.916(2) _cell_length_b 10.619(2) _cell_length_c 23.425(5) _cell_angle_alpha 90.00 _cell_angle_beta 96.04(3) _cell_angle_gamma 90.00 _cell_volume 2453.0(8) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 22343 _cell_measurement_theta_min 2.17 _cell_measurement_theta_max 27.48 _exptl_crystal_description plate _exptl_crystal_colour 'light yellow' _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.513 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1152 _exptl_absorpt_coefficient_mu 0.415 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8548 _exptl_absorpt_correction_T_max 0.9403 _exptl_absorpt_process_details 'ABSCOR by T.Higashi 8 March, 1995' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku raxis Rapid IP Area Detector' _diffrn_measurement_method '\w scans at fixed \c = 45\%' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7940 _diffrn_reflns_av_R_equivalents 0.0199 _diffrn_reflns_av_sigmaI/netI 0.0344 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4328 _reflns_number_gt 3672 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Rapid Auto(Rigaku 2001)' _computing_cell_refinement 'Rapid Auto(Rigaku 2001)' _computing_data_reduction 'Rapid Auto(Rigaku 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP in Siemens SHELXTL (Sheldrick, 1994)' _computing_publication_material 'SHELX97 (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^)+(0.0421P)^2^+0.8662P] 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 4328 _refine_ls_number_parameters 343 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0623 _refine_ls_R_factor_gt 0.0450 _refine_ls_wR_factor_ref 0.0993 _refine_ls_wR_factor_gt 0.0935 _refine_ls_goodness_of_fit_ref 1.168 _refine_ls_restrained_S_all 1.168 _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 S1B S -0.25452(6) 1.03837(6) 0.17552(3) 0.02780(17) Uani 1 1 d . . . S1A S 0.23493(6) 0.99164(6) 0.35009(3) 0.02780(17) Uani 1 1 d . . . S2A S 0.40632(6) 0.98828(6) 0.19911(3) 0.02859(17) Uani 1 1 d . . . S2B S -0.41299(6) 1.00451(6) 0.32962(3) 0.02734(17) Uani 1 1 d . . . N1A N 0.0926(2) 1.18690(18) 0.21994(8) 0.0239(5) Uani 1 1 d . . . H1AA H 0.0301 1.2397 0.2050 0.029 Uiso 1 1 calc R . . N1B N -0.0907(2) 0.83093(18) 0.29740(8) 0.0239(5) Uani 1 1 d . . . H1BA H -0.0246 0.7791 0.3096 0.029 Uiso 1 1 calc R . . C1B C -0.0724(3) 0.9737(2) 0.09638(11) 0.0286(6) Uani 1 1 d . . . H1BB H -0.1200 1.0266 0.0684 0.034 Uiso 1 1 calc R . . C1A C 0.0356(3) 1.0623(2) 0.42023(11) 0.0298(6) Uani 1 1 d . . . H1AB H 0.0775 1.0109 0.4502 0.036 Uiso 1 1 calc R . . C2A C -0.0803(3) 1.1301(3) 0.42777(11) 0.0317(6) Uani 1 1 d . . . H2AA H -0.1180 1.1256 0.4633 0.038 Uiso 1 1 calc R . . C2B C 0.0393(3) 0.9054(2) 0.08362(11) 0.0311(6) Uani 1 1 d . . . H2BA H 0.0674 0.9102 0.0462 0.037 Uiso 1 1 calc R . . C3B C 0.1110(3) 0.8298(2) 0.12468(11) 0.0287(6) Uani 1 1 d . . . H3BA H 0.1881 0.7846 0.1151 0.034 Uiso 1 1 calc R . . C3A C -0.1418(3) 1.2047(2) 0.38397(11) 0.0292(6) Uani 1 1 d . . . H3AA H -0.2214 1.2506 0.3899 0.035 Uiso 1 1 calc R . . C4A C -0.0896(3) 1.2133(2) 0.33207(11) 0.0273(6) Uani 1 1 d . . . H4AA H -0.1332 1.2641 0.3023 0.033 Uiso 1 1 calc R . . C4B C 0.0715(3) 0.8198(2) 0.17924(11) 0.0268(6) Uani 1 1 d . . . H4BA H 0.1216 0.7686 0.2072 0.032 Uiso 1 1 calc R . . C5B C -0.0422(2) 0.8852(2) 0.19303(10) 0.0223(5) Uani 1 1 d . . . C5A C 0.0275(2) 1.1471(2) 0.32346(10) 0.0225(5) Uani 1 1 d . . . C6A C 0.0891(2) 1.0707(2) 0.36817(10) 0.0248(5) Uani 1 1 d . . . C6B C -0.1134(2) 0.9629(2) 0.15129(10) 0.0238(5) Uani 1 1 d . . . C7A C 0.2154(2) 1.0599(2) 0.28235(10) 0.0222(5) Uani 1 1 d . . . C7B C -0.2234(2) 0.9624(2) 0.24124(10) 0.0235(5) Uani 1 1 d . . . C8A C 0.1035(2) 1.1384(2) 0.27471(10) 0.0220(5) Uani 1 1 d . . . C8B C -0.1088(2) 0.8879(2) 0.24435(10) 0.0216(5) Uani 1 1 d . . . C9B C -0.1943(2) 0.8695(2) 0.32783(10) 0.0235(5) Uani 1 1 d . . . C9A C 0.1976(2) 1.1377(2) 0.19270(10) 0.0223(5) Uani 1 1 d . . . C10A C 0.2757(2) 1.0603(2) 0.23041(10) 0.0238(5) Uani 1 1 d . . . C10B C -0.2790(2) 0.9500(2) 0.29405(10) 0.0224(5) Uani 1 1 d . . . C11A C 0.2376(2) 1.1396(2) 0.13585(10) 0.0240(5) Uani 1 1 d . . . C11B C -0.2334(2) 0.8488(2) 0.38417(10) 0.0241(5) Uani 1 1 d . . . C12B C -0.1750(3) 0.7756(2) 0.43007(11) 0.0295(6) Uani 1 1 d . . . H12A H -0.0957 0.7276 0.4262 0.035 Uiso 1 1 calc R . . C12A C 0.1813(3) 1.1993(2) 0.08576(11) 0.0302(6) Uani 1 1 d . . . H12B H 0.1057 1.2539 0.0867 0.036 Uiso 1 1 calc R . . C13B C -0.2335(3) 0.7741(3) 0.48062(11) 0.0330(6) Uani 1 1 d . . . H13A H -0.1945 0.7236 0.5116 0.040 Uiso 1 1 calc R . . C13A C 0.2360(3) 1.1783(3) 0.03502(11) 0.0335(6) Uani 1 1 d . . . H13B H 0.1984 1.2195 0.0010 0.040 Uiso 1 1 calc R . . C14B C -0.3491(3) 0.8452(3) 0.48747(11) 0.0345(6) Uani 1 1 d . . . H14A H -0.3872 0.8434 0.5230 0.041 Uiso 1 1 calc R . . C14A C 0.3459(3) 1.0974(3) 0.03290(11) 0.0379(7) Uani 1 1 d . . . H14B H 0.3810 1.0831 -0.0027 0.046 Uiso 1 1 calc R . . C15B C -0.4086(3) 0.9184(2) 0.44283(11) 0.0300(6) Uani 1 1 d . . . H15A H -0.4870 0.9673 0.4474 0.036 Uiso 1 1 calc R . . C15A C 0.4045(3) 1.0378(3) 0.08162(11) 0.0334(6) Uani 1 1 d . . . H15B H 0.4800 0.9832 0.0800 0.040 Uiso 1 1 calc R . . C16B C -0.3511(2) 0.9188(2) 0.39112(10) 0.0253(6) Uani 1 1 d . . . C16A C 0.3505(2) 1.0593(2) 0.13322(10) 0.0258(6) 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 S1B 0.0240(3) 0.0306(4) 0.0292(3) 0.0072(3) 0.0045(3) 0.0055(3) S1A 0.0244(3) 0.0311(4) 0.0276(3) 0.0066(3) 0.0018(3) 0.0050(3) S2A 0.0215(3) 0.0361(4) 0.0284(3) 0.0002(3) 0.0036(3) 0.0044(3) S2B 0.0217(3) 0.0331(4) 0.0275(3) 0.0034(3) 0.0036(2) 0.0052(3) N1A 0.0291(12) 0.0202(11) 0.0220(10) 0.0015(8) 0.0006(9) 0.0057(9) N1B 0.0216(11) 0.0211(11) 0.0290(11) 0.0019(9) 0.0019(9) 0.0047(8) C1B 0.0278(14) 0.0297(14) 0.0283(13) 0.0025(11) 0.0031(11) -0.0035(11) C1A 0.0319(15) 0.0304(15) 0.0269(14) 0.0036(11) 0.0024(11) -0.0034(12) C2A 0.0353(15) 0.0336(15) 0.0279(14) -0.0030(12) 0.0115(12) -0.0050(12) C2B 0.0341(16) 0.0330(15) 0.0276(14) -0.0047(12) 0.0096(12) -0.0071(12) C3B 0.0259(14) 0.0267(14) 0.0348(15) -0.0057(11) 0.0093(11) -0.0012(11) C3A 0.0277(15) 0.0266(14) 0.0344(14) -0.0060(12) 0.0080(11) -0.0003(11) C4A 0.0297(15) 0.0229(13) 0.0291(14) -0.0014(11) 0.0021(11) 0.0028(11) C4B 0.0261(14) 0.0211(13) 0.0326(14) -0.0021(11) 0.0003(11) -0.0001(10) C5B 0.0198(12) 0.0197(12) 0.0268(13) -0.0043(10) 0.0005(10) -0.0041(10) C5A 0.0252(13) 0.0194(13) 0.0228(12) -0.0023(10) 0.0020(10) -0.0047(10) C6A 0.0247(13) 0.0217(13) 0.0275(13) -0.0004(10) 0.0007(10) -0.0027(10) C6B 0.0209(13) 0.0214(13) 0.0289(13) -0.0023(10) 0.0013(10) -0.0036(10) C7A 0.0213(13) 0.0217(13) 0.0234(12) -0.0013(10) 0.0018(10) -0.0014(10) C7B 0.0227(13) 0.0222(13) 0.0250(13) 0.0009(10) 0.0000(10) -0.0010(10) C8A 0.0237(13) 0.0182(12) 0.0238(13) -0.0011(10) 0.0017(10) -0.0003(10) C8B 0.0206(12) 0.0189(12) 0.0248(13) -0.0002(10) -0.0002(10) -0.0027(10) C9B 0.0228(13) 0.0202(12) 0.0270(13) -0.0025(10) 0.0012(10) -0.0016(10) C9A 0.0227(13) 0.0196(12) 0.0242(13) -0.0025(10) 0.0009(10) -0.0020(10) C10A 0.0205(13) 0.0233(13) 0.0271(13) -0.0019(11) 0.0001(10) -0.0024(10) C10B 0.0206(13) 0.0225(13) 0.0245(13) 0.0005(10) 0.0033(10) 0.0011(10) C11A 0.0264(13) 0.0213(13) 0.0242(13) -0.0018(10) 0.0024(10) -0.0059(10) C11B 0.0273(14) 0.0197(12) 0.0246(13) -0.0036(10) -0.0005(10) -0.0044(10) C12B 0.0327(15) 0.0262(14) 0.0280(13) -0.0016(11) -0.0040(11) 0.0026(11) C12A 0.0315(15) 0.0264(14) 0.0319(14) -0.0011(11) 0.0000(11) -0.0044(11) C13B 0.0432(17) 0.0303(15) 0.0240(13) 0.0008(11) -0.0027(12) -0.0023(12) C13A 0.0391(17) 0.0384(16) 0.0226(13) 0.0011(12) 0.0012(11) -0.0088(13) C14B 0.0423(17) 0.0372(16) 0.0248(13) -0.0047(12) 0.0071(12) -0.0058(13) C14A 0.0385(17) 0.0529(19) 0.0238(14) -0.0068(13) 0.0097(12) -0.0108(14) C15B 0.0286(14) 0.0318(15) 0.0301(14) -0.0032(11) 0.0051(11) -0.0031(11) C15A 0.0279(15) 0.0414(16) 0.0318(15) -0.0071(12) 0.0070(12) -0.0043(12) C16B 0.0241(13) 0.0249(14) 0.0263(13) -0.0014(10) -0.0002(10) -0.0046(10) C16A 0.0224(13) 0.0272(14) 0.0274(13) -0.0024(11) 0.0013(10) -0.0059(10) _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 S1B C7B 1.737(2) . ? S1B C6B 1.758(2) . ? S1A C7A 1.737(2) . ? S1A C6A 1.761(3) . ? S2A C10A 1.732(2) . ? S2A C16A 1.755(3) . ? S2B C10B 1.740(2) . ? S2B C16B 1.759(3) . ? N1A C8A 1.376(3) . ? N1A C9A 1.380(3) . ? N1A H1AA 0.8800 . ? N1B C9B 1.373(3) . ? N1B C8B 1.377(3) . ? N1B H1BA 0.8800 . ? C1B C2B 1.383(4) . ? C1B C6B 1.394(3) . ? C1B H1BB 0.9500 . ? C1A C2A 1.383(4) . ? C1A C6A 1.383(3) . ? C1A H1AB 0.9500 . ? C2A C3A 1.386(4) . ? C2A H2AA 0.9500 . ? C2B C3B 1.389(4) . ? C2B H2BA 0.9500 . ? C3B C4B 1.380(3) . ? C3B H3BA 0.9500 . ? C3A C4A 1.374(3) . ? C3A H3AA 0.9500 . ? C4A C5A 1.389(3) . ? C4A H4AA 0.9500 . ? C4B C5B 1.391(3) . ? C4B H4BA 0.9500 . ? C5B C6B 1.410(3) . ? C5B C8B 1.432(3) . ? C5A C6A 1.413(3) . ? C5A C8A 1.436(3) . ? C7A C8A 1.384(3) . ? C7A C10A 1.411(3) . ? C7B C8B 1.380(3) . ? C7B C10B 1.412(3) . ? C9B C10B 1.386(3) . ? C9B C11B 1.431(3) . ? C9A C10A 1.382(3) . ? C9A C11A 1.429(3) . ? C11A C12A 1.397(3) . ? C11A C16A 1.413(3) . ? C11B C12B 1.402(3) . ? C11B C16B 1.407(3) . ? C12B C13B 1.372(4) . ? C12B H12A 0.9500 . ? C12A C13A 1.376(4) . ? C12A H12B 0.9500 . ? C13B C14B 1.396(4) . ? C13B H13A 0.9500 . ? C13A C14A 1.392(4) . ? C13A H13B 0.9500 . ? C14B C15B 1.384(4) . ? C14B H14A 0.9500 . ? C14A C15A 1.380(4) . ? C14A H14B 0.9500 . ? C15B C16B 1.392(3) . ? C15B H15A 0.9500 . ? C15A C16A 1.391(3) . ? C15A H15B 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 C7B S1B C6B 90.06(12) . . ? C7A S1A C6A 90.30(12) . . ? C10A S2A C16A 90.11(12) . . ? C10B S2B C16B 90.11(12) . . ? C8A N1A C9A 107.45(19) . . ? C8A N1A H1AA 126.3 . . ? C9A N1A H1AA 126.3 . . ? C9B N1B C8B 107.66(19) . . ? C9B N1B H1BA 126.2 . . ? C8B N1B H1BA 126.2 . . ? C2B C1B C6B 118.3(2) . . ? C2B C1B H1BB 120.9 . . ? C6B C1B H1BB 120.9 . . ? C2A C1A C6A 118.7(2) . . ? C2A C1A H1AB 120.7 . . ? C6A C1A H1AB 120.7 . . ? C1A C2A C3A 120.7(2) . . ? C1A C2A H2AA 119.7 . . ? C3A C2A H2AA 119.7 . . ? C1B C2B C3B 121.1(2) . . ? C1B C2B H2BA 119.4 . . ? C3B C2B H2BA 119.4 . . ? C4B C3B C2B 120.7(2) . . ? C4B C3B H3BA 119.6 . . ? C2B C3B H3BA 119.6 . . ? C4A C3A C2A 121.0(2) . . ? C4A C3A H3AA 119.5 . . ? C2A C3A H3AA 119.5 . . ? C3A C4A C5A 119.6(2) . . ? C3A C4A H4AA 120.2 . . ? C5A C4A H4AA 120.2 . . ? C3B C4B C5B 119.5(2) . . ? C3B C4B H4BA 120.2 . . ? C5B C4B H4BA 120.2 . . ? C4B C5B C6B 119.3(2) . . ? C4B C5B C8B 131.4(2) . . ? C6B C5B C8B 109.2(2) . . ? C4A C5A C6A 119.1(2) . . ? C4A C5A C8A 131.6(2) . . ? C6A C5A C8A 109.3(2) . . ? C1A C6A C5A 120.9(2) . . ? C1A C6A S1A 125.6(2) . . ? C5A C6A S1A 113.45(18) . . ? C1B C6B C5B 121.0(2) . . ? C1B C6B S1B 125.4(2) . . ? C5B C6B S1B 113.58(18) . . ? C8A C7A C10A 107.1(2) . . ? C8A C7A S1A 112.35(18) . . ? C10A C7A S1A 140.56(19) . . ? C8B C7B C10B 107.2(2) . . ? C8B C7B S1B 112.44(18) . . ? C10B C7B S1B 140.4(2) . . ? N1A C8A C7A 109.2(2) . . ? N1A C8A C5A 136.1(2) . . ? C7A C8A C5A 114.6(2) . . ? N1B C8B C7B 109.2(2) . . ? N1B C8B C5B 136.2(2) . . ? C7B C8B C5B 114.6(2) . . ? N1B C9B C10B 109.2(2) . . ? N1B C9B C11B 136.3(2) . . ? C10B C9B C11B 114.5(2) . . ? N1A C9A C10A 109.2(2) . . ? N1A C9A C11A 136.3(2) . . ? C10A C9A C11A 114.3(2) . . ? C9A C10A C7A 107.0(2) . . ? C9A C10A S2A 112.68(18) . . ? C7A C10A S2A 140.1(2) . . ? C9B C10B C7B 106.8(2) . . ? C9B C10B S2B 112.25(18) . . ? C7B C10B S2B 140.93(19) . . ? C12A C11A C16A 119.0(2) . . ? C12A C11A C9A 131.5(2) . . ? C16A C11A C9A 109.3(2) . . ? C12B C11B C16B 119.0(2) . . ? C12B C11B C9B 131.5(2) . . ? C16B C11B C9B 109.5(2) . . ? C13B C12B C11B 119.4(2) . . ? C13B C12B H12A 120.3 . . ? C11B C12B H12A 120.3 . . ? C13A C12A C11A 119.5(3) . . ? C13A C12A H12B 120.2 . . ? C11A C12A H12B 120.2 . . ? C12B C13B C14B 121.3(2) . . ? C12B C13B H13A 119.4 . . ? C14B C13B H13A 119.4 . . ? C12A C13A C14A 120.8(3) . . ? C12A C13A H13B 119.6 . . ? C14A C13A H13B 119.6 . . ? C15B C14B C13B 120.5(2) . . ? C15B C14B H14A 119.8 . . ? C13B C14B H14A 119.8 . . ? C15A C14A C13A 121.2(3) . . ? C15A C14A H14B 119.4 . . ? C13A C14A H14B 119.4 . . ? C14B C15B C16B 118.6(2) . . ? C14B C15B H15A 120.7 . . ? C16B C15B H15A 120.7 . . ? C14A C15A C16A 118.4(3) . . ? C14A C15A H15B 120.8 . . ? C16A C15A H15B 120.8 . . ? C15B C16B C11B 121.3(2) . . ? C15B C16B S2B 125.1(2) . . ? C11B C16B S2B 113.61(18) . . ? C15A C16A C11A 121.1(2) . . ? C15A C16A S2A 125.4(2) . . ? C11A C16A S2A 113.50(18) . . ? 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 C6A C1A C2A C3A 0.3(4) . . . . ? C6B C1B C2B C3B -1.4(4) . . . . ? C1B C2B C3B C4B 0.8(4) . . . . ? C1A C2A C3A C4A -0.1(4) . . . . ? C2A C3A C4A C5A -0.6(4) . . . . ? C2B C3B C4B C5B 0.6(4) . . . . ? C3B C4B C5B C6B -1.4(3) . . . . ? C3B C4B C5B C8B 176.8(2) . . . . ? C3A C4A C5A C6A 1.0(4) . . . . ? C3A C4A C5A C8A -180.0(2) . . . . ? C2A C1A C6A C5A 0.2(4) . . . . ? C2A C1A C6A S1A -179.80(19) . . . . ? C4A C5A C6A C1A -0.8(4) . . . . ? C8A C5A C6A C1A 180.0(2) . . . . ? C4A C5A C6A S1A 179.19(18) . . . . ? C8A C5A C6A S1A -0.1(3) . . . . ? C7A S1A C6A C1A 180.0(2) . . . . ? C7A S1A C6A C5A 0.02(19) . . . . ? C2B C1B C6B C5B 0.6(4) . . . . ? C2B C1B C6B S1B -178.37(19) . . . . ? C4B C5B C6B C1B 0.8(3) . . . . ? C8B C5B C6B C1B -177.7(2) . . . . ? C4B C5B C6B S1B 179.85(18) . . . . ? C8B C5B C6B S1B 1.3(2) . . . . ? C7B S1B C6B C1B 177.1(2) . . . . ? C7B S1B C6B C5B -1.95(18) . . . . ? C6A S1A C7A C8A 0.02(19) . . . . ? C6A S1A C7A C10A -178.1(3) . . . . ? C6B S1B C7B C8B 2.09(19) . . . . ? C6B S1B C7B C10B -176.9(3) . . . . ? C9A N1A C8A C7A 0.6(3) . . . . ? C9A N1A C8A C5A -177.6(3) . . . . ? C10A C7A C8A N1A 0.1(3) . . . . ? S1A C7A C8A N1A -178.72(16) . . . . ? C10A C7A C8A C5A 178.7(2) . . . . ? S1A C7A C8A C5A -0.1(3) . . . . ? C4A C5A C8A N1A -0.9(5) . . . . ? C6A C5A C8A N1A 178.2(3) . . . . ? C4A C5A C8A C7A -179.0(2) . . . . ? C6A C5A C8A C7A 0.1(3) . . . . ? C9B N1B C8B C7B 0.1(3) . . . . ? C9B N1B C8B C5B -177.6(3) . . . . ? C10B C7B C8B N1B -0.7(3) . . . . ? S1B C7B C8B N1B 179.98(16) . . . . ? C10B C7B C8B C5B 177.6(2) . . . . ? S1B C7B C8B C5B -1.8(3) . . . . ? C4B C5B C8B N1B -0.4(5) . . . . ? C6B C5B C8B N1B 177.9(3) . . . . ? C4B C5B C8B C7B -178.0(2) . . . . ? C6B C5B C8B C7B 0.3(3) . . . . ? C8B N1B C9B C10B 0.5(3) . . . . ? C8B N1B C9B C11B -178.4(3) . . . . ? C8A N1A C9A C10A -1.0(3) . . . . ? C8A N1A C9A C11A 173.2(3) . . . . ? N1A C9A C10A C7A 1.1(3) . . . . ? C11A C9A C10A C7A -174.5(2) . . . . ? N1A C9A C10A S2A 177.34(16) . . . . ? C11A C9A C10A S2A 1.7(3) . . . . ? C8A C7A C10A C9A -0.7(3) . . . . ? S1A C7A C10A C9A 177.5(2) . . . . ? C8A C7A C10A S2A -175.3(2) . . . . ? S1A C7A C10A S2A 2.9(5) . . . . ? C16A S2A C10A C9A -2.13(19) . . . . ? C16A S2A C10A C7A 172.3(3) . . . . ? N1B C9B C10B C7B -0.9(3) . . . . ? C11B C9B C10B C7B 178.3(2) . . . . ? N1B C9B C10B S2B -179.59(16) . . . . ? C11B C9B C10B S2B -0.4(3) . . . . ? C8B C7B C10B C9B 1.0(3) . . . . ? S1B C7B C10B C9B -180.0(2) . . . . ? C8B C7B C10B S2B 179.0(2) . . . . ? S1B C7B C10B S2B -1.9(5) . . . . ? C16B S2B C10B C9B 0.89(19) . . . . ? C16B S2B C10B C7B -177.1(3) . . . . ? N1A C9A C11A C12A 2.2(5) . . . . ? C10A C9A C11A C12A 176.2(2) . . . . ? N1A C9A C11A C16A -174.2(3) . . . . ? C10A C9A C11A C16A -0.2(3) . . . . ? N1B C9B C11B C12B -0.8(5) . . . . ? C10B C9B C11B C12B -179.8(2) . . . . ? N1B C9B C11B C16B 178.4(3) . . . . ? C10B C9B C11B C16B -0.5(3) . . . . ? C16B C11B C12B C13B -0.2(4) . . . . ? C9B C11B C12B C13B 179.0(3) . . . . ? C16A C11A C12A C13A 0.4(4) . . . . ? C9A C11A C12A C13A -175.7(2) . . . . ? C11B C12B C13B C14B -0.8(4) . . . . ? C11A C12A C13A C14A 0.6(4) . . . . ? C12B C13B C14B C15B 0.7(4) . . . . ? C12A C13A C14A C15A -1.2(4) . . . . ? C13B C14B C15B C16B 0.4(4) . . . . ? C13A C14A C15A C16A 0.6(4) . . . . ? C14B C15B C16B C11B -1.3(4) . . . . ? C14B C15B C16B S2B 179.45(19) . . . . ? C12B C11B C16B C15B 1.2(4) . . . . ? C9B C11B C16B C15B -178.1(2) . . . . ? C12B C11B C16B S2B -179.46(18) . . . . ? C9B C11B C16B S2B 1.2(3) . . . . ? C10B S2B C16B C15B 178.1(2) . . . . ? C10B S2B C16B C11B -1.21(19) . . . . ? C14A C15A C16A C11A 0.5(4) . . . . ? C14A C15A C16A S2A 177.5(2) . . . . ? C12A C11A C16A C15A -1.0(4) . . . . ? C9A C11A C16A C15A 175.9(2) . . . . ? C12A C11A C16A S2A -178.32(18) . . . . ? C9A C11A C16A S2A -1.5(3) . . . . ? C10A S2A C16A C15A -175.2(2) . . . . ? C10A S2A C16A C11A 2.07(19) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.314 _refine_diff_density_min -0.269 _refine_diff_density_rms 0.052 # Attachment '7.cif' data_r80427j1 _database_code_depnum_ccdc_archive 'CCDC 697267' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H21 N S2' _chemical_formula_weight 363.52 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 P2(1)/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 11.582(2) _cell_length_b 8.1596(16) _cell_length_c 19.770(4) _cell_angle_alpha 90.00 _cell_angle_beta 106.89(3) _cell_angle_gamma 90.00 _cell_volume 1787.7(6) _cell_formula_units_Z 4 _cell_measurement_temperature 113(2) _cell_measurement_reflns_used 4801 _cell_measurement_theta_min 2.390 _cell_measurement_theta_max 27.884 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.351 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 768 _exptl_absorpt_coefficient_mu 0.302 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.9589 _exptl_absorpt_correction_T_max 0.9880 _exptl_absorpt_process_details crystalclear _exptl_special_details ; ? ; _diffrn_ambient_temperature 113(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type 'rigaku saturn' _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 _diffrn_reflns_number 12637 _diffrn_reflns_av_R_equivalents 0.0717 _diffrn_reflns_av_sigmaI/netI 0.0681 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.84 _diffrn_reflns_theta_max 27.87 _reflns_number_total 4248 _reflns_number_gt 3441 _reflns_threshold_expression >2sigma(I) _computing_data_collection crystalclear _computing_cell_refinement crystalclear _computing_data_reduction crystalclear _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0563P)^2^+0.0119P] 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 4248 _refine_ls_number_parameters 227 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0567 _refine_ls_R_factor_gt 0.0420 _refine_ls_wR_factor_ref 0.1106 _refine_ls_wR_factor_gt 0.1046 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _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 0.90319(4) 0.52559(5) 0.042930(18) 0.01639(12) Uani 1 1 d . . . S2 S 1.26979(4) 0.51766(5) 0.137294(19) 0.01777(12) Uani 1 1 d . . . N1 N 1.04684(12) 0.67980(15) 0.23227(6) 0.0156(3) Uani 1 1 d . . . C1 C 0.78732(15) 0.59847(18) 0.07596(8) 0.0166(3) Uani 1 1 d . . . C2 C 0.66599(15) 0.6025(2) 0.03788(8) 0.0204(3) Uani 1 1 d . . . H2 H 0.6398 0.5584 -0.0074 0.024 Uiso 1 1 calc R . . C3 C 0.58438(16) 0.6736(2) 0.06855(9) 0.0235(4) Uani 1 1 d . . . H3 H 0.5029 0.6788 0.0436 0.028 Uiso 1 1 calc R . . C4 C 0.62510(16) 0.7375(2) 0.13723(9) 0.0233(4) Uani 1 1 d . . . H4 H 0.5700 0.7860 0.1571 0.028 Uiso 1 1 calc R . . C5 C 0.74457(16) 0.72996(18) 0.17574(8) 0.0202(3) Uani 1 1 d . . . H5 H 0.7692 0.7706 0.2217 0.024 Uiso 1 1 calc R . . C6 C 0.82970(15) 0.66090(17) 0.14585(7) 0.0159(3) Uani 1 1 d . . . C7 C 0.95862(14) 0.64518(17) 0.17061(7) 0.0152(3) Uani 1 1 d . . . C8 C 1.01109(14) 0.57943(17) 0.12129(7) 0.0141(3) Uani 1 1 d . . . C9 C 1.13656(14) 0.57437(18) 0.15445(7) 0.0149(3) Uani 1 1 d . . . C10 C 1.15658(15) 0.63665(17) 0.22273(7) 0.0148(3) Uani 1 1 d . . . C11 C 1.28087(15) 0.64477(18) 0.26316(7) 0.0177(3) Uani 1 1 d . . . C12 C 1.33978(16) 0.7024(2) 0.33141(8) 0.0229(4) Uani 1 1 d . . . H12 H 1.2952 0.7474 0.3591 0.027 Uiso 1 1 calc R . . C13 C 1.46392(17) 0.6923(2) 0.35753(8) 0.0276(4) Uani 1 1 d . . . H13 H 1.5022 0.7316 0.4026 0.033 Uiso 1 1 calc R . . C14 C 1.53276(17) 0.6241(2) 0.31719(9) 0.0266(4) Uani 1 1 d . . . H14 H 1.6161 0.6172 0.3360 0.032 Uiso 1 1 calc R . . C15 C 1.47847(16) 0.5668(2) 0.24986(8) 0.0227(4) Uani 1 1 d . . . H15 H 1.5243 0.5211 0.2231 0.027 Uiso 1 1 calc R . . C16 C 1.35340(15) 0.57892(18) 0.22275(7) 0.0175(3) Uani 1 1 d . . . C17 C 1.02218(15) 0.72162(18) 0.29909(7) 0.0167(3) Uani 1 1 d . . . H17A H 0.9635 0.8098 0.2908 0.020 Uiso 1 1 calc R . . H17B H 1.0959 0.7603 0.3327 0.020 Uiso 1 1 calc R . . C18 C 0.97392(16) 0.57456(18) 0.33050(8) 0.0189(3) Uani 1 1 d . . . H18A H 0.9108 0.5218 0.2937 0.023 Uiso 1 1 calc R . . H18B H 1.0385 0.4958 0.3478 0.023 Uiso 1 1 calc R . . C19 C 0.92379(15) 0.62367(18) 0.39075(8) 0.0184(3) Uani 1 1 d . . . H19A H 0.8685 0.7147 0.3753 0.022 Uiso 1 1 calc R . . H19B H 0.9898 0.6614 0.4302 0.022 Uiso 1 1 calc R . . C20 C 0.85779(16) 0.48526(18) 0.41627(8) 0.0183(3) Uani 1 1 d . . . H20A H 0.7955 0.4414 0.3764 0.022 Uiso 1 1 calc R . . H20B H 0.9144 0.3977 0.4357 0.022 Uiso 1 1 calc R . . C21 C 0.80050(16) 0.5437(2) 0.47240(8) 0.0210(4) Uani 1 1 d . . . H21A H 0.7522 0.6403 0.4551 0.025 Uiso 1 1 calc R . . H21B H 0.8639 0.5749 0.5145 0.025 Uiso 1 1 calc R . . C22 C 0.72085(19) 0.4137(2) 0.49221(10) 0.0332(4) Uani 1 1 d . . . H22A H 0.6582 0.3815 0.4507 0.050 Uiso 1 1 calc R . . H22B H 0.6853 0.4581 0.5265 0.050 Uiso 1 1 calc R . . H22C H 0.7690 0.3199 0.5119 0.050 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 0.0149(2) 0.0209(2) 0.01304(19) -0.00098(13) 0.00355(16) 0.00190(14) S2 0.0149(2) 0.0236(2) 0.0150(2) -0.00172(13) 0.00474(17) -0.00013(15) N1 0.0175(8) 0.0153(6) 0.0140(6) -0.0010(5) 0.0046(5) 0.0010(5) C1 0.0172(9) 0.0153(7) 0.0180(7) 0.0019(5) 0.0064(7) 0.0008(6) C2 0.0185(10) 0.0236(8) 0.0184(7) 0.0014(6) 0.0043(7) 0.0004(7) C3 0.0180(10) 0.0252(9) 0.0269(8) 0.0040(6) 0.0057(7) 0.0028(7) C4 0.0217(10) 0.0214(8) 0.0303(8) 0.0020(6) 0.0129(8) 0.0044(7) C5 0.0225(10) 0.0176(8) 0.0220(7) -0.0006(6) 0.0090(7) 0.0016(6) C6 0.0170(9) 0.0138(7) 0.0172(7) 0.0030(5) 0.0055(7) 0.0012(6) C7 0.0185(9) 0.0116(7) 0.0156(6) 0.0011(5) 0.0054(6) 0.0007(6) C8 0.0161(9) 0.0125(7) 0.0131(6) 0.0008(5) 0.0035(6) -0.0005(5) C9 0.0164(9) 0.0145(7) 0.0142(7) 0.0019(5) 0.0051(6) -0.0008(6) C10 0.0168(9) 0.0143(7) 0.0139(6) 0.0005(5) 0.0055(6) -0.0018(6) C11 0.0198(10) 0.0152(7) 0.0178(7) 0.0017(5) 0.0052(7) -0.0035(6) C12 0.0230(10) 0.0262(9) 0.0188(7) -0.0025(6) 0.0050(7) -0.0032(7) C13 0.0261(11) 0.0318(10) 0.0206(8) -0.0036(7) 0.0000(8) -0.0058(8) C14 0.0166(10) 0.0318(10) 0.0268(8) 0.0033(7) -0.0008(8) -0.0047(7) C15 0.0183(10) 0.0266(9) 0.0229(8) 0.0022(6) 0.0054(7) -0.0025(7) C16 0.0196(9) 0.0170(8) 0.0156(7) 0.0016(5) 0.0044(7) -0.0024(6) C17 0.0202(9) 0.0171(7) 0.0139(7) -0.0037(5) 0.0065(6) 0.0004(6) C18 0.0247(10) 0.0157(7) 0.0179(7) -0.0015(5) 0.0085(7) 0.0012(6) C19 0.0223(10) 0.0168(7) 0.0173(7) -0.0014(5) 0.0075(7) 0.0011(6) C20 0.0181(10) 0.0171(8) 0.0200(7) -0.0016(5) 0.0060(7) -0.0011(6) C21 0.0212(10) 0.0227(8) 0.0198(7) 0.0007(6) 0.0072(7) 0.0011(7) C22 0.0338(12) 0.0316(10) 0.0408(10) 0.0061(8) 0.0213(10) -0.0012(8) _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 C8 1.7405(17) . ? S1 C1 1.7580(15) . ? S2 C9 1.7362(16) . ? S2 C16 1.7582(17) . ? N1 C7 1.373(2) . ? N1 C10 1.384(2) . ? N1 C17 1.4706(16) . ? C1 C2 1.388(2) . ? C1 C6 1.420(2) . ? C2 C3 1.389(2) . ? C2 H2 0.9300 . ? C3 C4 1.402(2) . ? C3 H3 0.9300 . ? C4 C5 1.373(2) . ? C4 H4 0.9300 . ? C5 C6 1.406(2) . ? C5 H5 0.9300 . ? C6 C7 1.436(2) . ? C7 C8 1.3972(18) . ? C8 C9 1.411(2) . ? C9 C10 1.3974(19) . ? C10 C11 1.431(2) . ? C11 C12 1.404(2) . ? C11 C16 1.422(2) . ? C12 C13 1.382(3) . ? C12 H12 0.9300 . ? C13 C14 1.397(2) . ? C13 H13 0.9300 . ? C14 C15 1.378(2) . ? C14 H14 0.9300 . ? C15 C16 1.394(2) . ? C15 H15 0.9300 . ? C17 C18 1.530(2) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 C19 1.5227(18) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 C20 1.529(2) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 C21 1.525(2) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 C22 1.529(2) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? 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 C8 S1 C1 90.70(7) . . ? C9 S2 C16 90.52(8) . . ? C7 N1 C10 107.62(11) . . ? C7 N1 C17 123.82(13) . . ? C10 N1 C17 127.40(13) . . ? C2 C1 C6 121.90(13) . . ? C2 C1 S1 124.62(11) . . ? C6 C1 S1 113.43(12) . . ? C1 C2 C3 118.88(15) . . ? C1 C2 H2 120.6 . . ? C3 C2 H2 120.6 . . ? C2 C3 C4 119.85(17) . . ? C2 C3 H3 120.1 . . ? C4 C3 H3 120.1 . . ? C5 C4 C3 121.44(15) . . ? C5 C4 H4 119.3 . . ? C3 C4 H4 119.3 . . ? C4 C5 C6 120.09(14) . . ? C4 C5 H5 120.0 . . ? C6 C5 H5 120.0 . . ? C5 C6 C1 117.80(15) . . ? C5 C6 C7 132.79(14) . . ? C1 C6 C7 109.33(13) . . ? N1 C7 C8 109.64(13) . . ? N1 C7 C6 135.74(12) . . ? C8 C7 C6 114.62(13) . . ? C7 C8 C9 106.57(13) . . ? C7 C8 S1 111.88(12) . . ? C9 C8 S1 141.49(11) . . ? C10 C9 C8 107.32(13) . . ? C10 C9 S2 112.22(12) . . ? C8 C9 S2 140.46(11) . . ? N1 C10 C9 108.85(14) . . ? N1 C10 C11 136.65(13) . . ? C9 C10 C11 114.46(13) . . ? C12 C11 C16 117.70(15) . . ? C12 C11 C10 132.95(14) . . ? C16 C11 C10 109.36(13) . . ? C13 C12 C11 120.10(15) . . ? C13 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? C12 C13 C14 120.99(16) . . ? C12 C13 H13 119.5 . . ? C14 C13 H13 119.5 . . ? C15 C14 C13 120.70(17) . . ? C15 C14 H14 119.6 . . ? C13 C14 H14 119.6 . . ? C14 C15 C16 118.61(15) . . ? C14 C15 H15 120.7 . . ? C16 C15 H15 120.7 . . ? C15 C16 C11 121.88(14) . . ? C15 C16 S2 124.74(12) . . ? C11 C16 S2 113.38(13) . . ? N1 C17 C18 111.83(12) . . ? N1 C17 H17A 109.3 . . ? C18 C17 H17A 109.3 . . ? N1 C17 H17B 109.3 . . ? C18 C17 H17B 109.3 . . ? H17A C17 H17B 107.9 . . ? C19 C18 C17 112.24(12) . . ? C19 C18 H18A 109.2 . . ? C17 C18 H18A 109.2 . . ? C19 C18 H18B 109.2 . . ? C17 C18 H18B 109.2 . . ? H18A C18 H18B 107.9 . . ? C18 C19 C20 113.87(13) . . ? C18 C19 H19A 108.8 . . ? C20 C19 H19A 108.8 . . ? C18 C19 H19B 108.8 . . ? C20 C19 H19B 108.8 . . ? H19A C19 H19B 107.7 . . ? C21 C20 C19 111.97(13) . . ? C21 C20 H20A 109.2 . . ? C19 C20 H20A 109.2 . . ? C21 C20 H20B 109.2 . . ? C19 C20 H20B 109.2 . . ? H20A C20 H20B 107.9 . . ? C20 C21 C22 113.08(14) . . ? C20 C21 H21A 109.0 . . ? C22 C21 H21A 109.0 . . ? C20 C21 H21B 109.0 . . ? C22 C21 H21B 109.0 . . ? H21A C21 H21B 107.8 . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? 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 C8 S1 C1 C2 176.75(14) . . . . ? C8 S1 C1 C6 -0.76(11) . . . . ? C6 C1 C2 C3 1.7(2) . . . . ? S1 C1 C2 C3 -175.63(12) . . . . ? C1 C2 C3 C4 -0.9(2) . . . . ? C2 C3 C4 C5 -0.7(2) . . . . ? C3 C4 C5 C6 1.6(2) . . . . ? C4 C5 C6 C1 -0.9(2) . . . . ? C4 C5 C6 C7 175.60(15) . . . . ? C2 C1 C6 C5 -0.8(2) . . . . ? S1 C1 C6 C5 176.79(11) . . . . ? C2 C1 C6 C7 -178.05(13) . . . . ? S1 C1 C6 C7 -0.46(15) . . . . ? C10 N1 C7 C8 0.12(16) . . . . ? C17 N1 C7 C8 -168.34(12) . . . . ? C10 N1 C7 C6 -179.58(16) . . . . ? C17 N1 C7 C6 12.0(3) . . . . ? C5 C6 C7 N1 4.9(3) . . . . ? C1 C6 C7 N1 -178.42(15) . . . . ? C5 C6 C7 C8 -174.80(15) . . . . ? C1 C6 C7 C8 1.89(17) . . . . ? N1 C7 C8 C9 -0.15(16) . . . . ? C6 C7 C8 C9 179.62(12) . . . . ? N1 C7 C8 S1 177.73(9) . . . . ? C6 C7 C8 S1 -2.50(16) . . . . ? C1 S1 C8 C7 1.82(11) . . . . ? C1 S1 C8 C9 178.55(18) . . . . ? C7 C8 C9 C10 0.12(16) . . . . ? S1 C8 C9 C10 -176.72(14) . . . . ? C7 C8 C9 S2 -179.46(14) . . . . ? S1 C8 C9 S2 3.7(3) . . . . ? C16 S2 C9 C10 -0.17(12) . . . . ? C16 S2 C9 C8 179.39(18) . . . . ? C7 N1 C10 C9 -0.05(16) . . . . ? C17 N1 C10 C9 167.88(13) . . . . ? C7 N1 C10 C11 177.47(16) . . . . ? C17 N1 C10 C11 -14.6(3) . . . . ? C8 C9 C10 N1 -0.05(16) . . . . ? S2 C9 C10 N1 179.66(9) . . . . ? C8 C9 C10 C11 -178.17(12) . . . . ? S2 C9 C10 C11 1.54(17) . . . . ? N1 C10 C11 C12 0.3(3) . . . . ? C9 C10 C11 C12 177.75(16) . . . . ? N1 C10 C11 C16 -179.81(16) . . . . ? C9 C10 C11 C16 -2.39(18) . . . . ? C16 C11 C12 C13 -0.8(2) . . . . ? C10 C11 C12 C13 179.09(16) . . . . ? C11 C12 C13 C14 -0.5(3) . . . . ? C12 C13 C14 C15 0.8(3) . . . . ? C13 C14 C15 C16 0.2(3) . . . . ? C14 C15 C16 C11 -1.5(2) . . . . ? C14 C15 C16 S2 178.13(12) . . . . ? C12 C11 C16 C15 1.8(2) . . . . ? C10 C11 C16 C15 -178.10(14) . . . . ? C12 C11 C16 S2 -177.89(12) . . . . ? C10 C11 C16 S2 2.23(16) . . . . ? C9 S2 C16 C15 179.12(15) . . . . ? C9 S2 C16 C11 -1.22(12) . . . . ? C7 N1 C17 C18 69.24(18) . . . . ? C10 N1 C17 C18 -96.88(18) . . . . ? N1 C17 C18 C19 -168.12(13) . . . . ? C17 C18 C19 C20 171.36(14) . . . . ? C18 C19 C20 C21 -175.39(14) . . . . ? C19 C20 C21 C22 172.82(15) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.87 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.357 _refine_diff_density_min -0.367 _refine_diff_density_rms 0.063