# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 #TrackingRef 'new.cif' #====================================================================== _audit_creation_method SHELXL-97 # PROCESSING SUMMARY (IUCr Office Use Only) _journal_data_validation_number ? _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_date_from_coeditor ? _journal_date_accepted ? _journal_date_printers_first ? _journal_date_printers_final ? _journal_date_proofs_out ? _journal_date_proofs_in ? _journal_coeditor_name ? _journal_coeditor_code ? _journal_coeditor_notes ; ? ; _journal_techeditor_code ? _journal_techeditor_notes ; ? ; _journal_coden_ASTM ? _journal_year ? _journal_volume ? _journal_issue ? _journal_page_first ? _journal_page_last ? _journal_paper_category ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? #======================================================================= # SUBMISSION DETAILS _publ_contact_author_name 'Sundarababu Baskaran' _publ_contact_author_address ; Department of Chemistry Indian Institute of Technology Madras Chennai-600 036 India ; _publ_contact_author_email sbhaskar@iitm.ac.in _publ_contact_author_fax ' ' _publ_contact_author_phone '91 44 2257 4218' #======================================================================= _publ_section_title ; Concise Synthesis of Bridged Azatricyclic Framework via Domino Semipinacol-Schmidt Reaction ; # TITLE AND AUTHOR LIST loop_ _publ_author_name _publ_author_address 'Manohar Puppala' ; Department of Chemistry Indian Institute of Technology Madras Chennai-600 036 India ; 'Sundarababu Baskaran' ; Department of Chemistry, Indian Institute of Technology - Madras Chennai-600 036 India ; #===================================================================== data_new _database_code_depnum_ccdc_archive 'CCDC 840274' #TrackingRef 'new.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H15 N S ' _chemical_formula_sum 'C10 H15 N S' _chemical_formula_weight 181.29 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 Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.3690(3) _cell_length_b 10.7722(3) _cell_length_c 11.8003(5) _cell_angle_alpha 106.662(2) _cell_angle_beta 102.457(2) _cell_angle_gamma 113.512(2) _cell_volume 969.54(6) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3269 _cell_measurement_theta_min 2.44 _cell_measurement_theta_max 24.37 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.242 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 392 _exptl_absorpt_coefficient_mu 0.279 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.935 _exptl_absorpt_correction_T_max 0.959 _exptl_absorpt_process_details SADABS(Bruker,2004) _exptl_special_details ; ? ; _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 APEXII CCD area detector' _diffrn_measurement_method 'Phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13277 _diffrn_reflns_av_R_equivalents 0.0313 _diffrn_reflns_av_sigmaI/netI 0.0451 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.94 _diffrn_reflns_theta_max 28.30 _reflns_number_total 4601 _reflns_number_gt 2703 _reflns_threshold_expression >2sigma(I) _computing_data_collection APEXII,Bruker,2004 _computing_cell_refinement APEXII,Bruker,2004 _computing_data_reduction SAINT,Bruker,2004 _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] 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 4601 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1030 _refine_ls_R_factor_gt 0.0516 _refine_ls_wR_factor_ref 0.1801 _refine_ls_wR_factor_gt 0.1482 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _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 C1 C 0.1988(4) 0.2274(3) 0.3525(3) 0.0746(8) Uani 1 1 d . . . H1A H 0.1295 0.2234 0.4031 0.090 Uiso 1 1 calc R . . H1B H 0.2591 0.3289 0.3614 0.090 Uiso 1 1 calc R . . C2 C 0.0909(4) 0.1210(4) 0.2124(3) 0.0819(9) Uani 1 1 d . . . H2A H -0.0261 0.0670 0.2009 0.098 Uiso 1 1 calc R . . H2B H 0.1003 0.1753 0.1590 0.098 Uiso 1 1 calc R . . C3 C 0.1594(3) 0.0150(3) 0.1793(2) 0.0682(8) Uani 1 1 d . . . H3 H 0.1504 -0.0163 0.0903 0.082 Uiso 1 1 calc R . . C4 C 0.0717(4) -0.1189(3) 0.2089(2) 0.0741(8) Uani 1 1 d . . . H4A H -0.0439 -0.1804 0.1489 0.089 Uiso 1 1 calc R . . H4B H 0.1269 -0.1783 0.1979 0.089 Uiso 1 1 calc R . . C5 C 0.0744(3) -0.0722(3) 0.3421(2) 0.0674(7) Uani 1 1 d . . . H5A H -0.0103 -0.0428 0.3459 0.081 Uiso 1 1 calc R . . H5B H 0.0480 -0.1556 0.3657 0.081 Uiso 1 1 calc R . . C6 C 0.3258(3) 0.0622(3) 0.5404(2) 0.0487(6) Uani 1 1 d . . . C7 C 0.4903(3) 0.2029(3) 0.5974(2) 0.0700(8) Uani 1 1 d . . . H7A H 0.5093 0.2632 0.6837 0.084 Uiso 1 1 calc R . . H7B H 0.5814 0.1809 0.6000 0.084 Uiso 1 1 calc R . . C8 C 0.4816(3) 0.2834(3) 0.5146(2) 0.0734(8) Uani 1 1 d . . . H8A H 0.5796 0.3132 0.4918 0.088 Uiso 1 1 calc R . . H8B H 0.4765 0.3717 0.5586 0.088 Uiso 1 1 calc R . . C9 C 0.3217(3) 0.1743(2) 0.3952(2) 0.0486(6) Uani 1 1 d . . . C10 C 0.3422(3) 0.1094(3) 0.2716(2) 0.0579(6) Uani 1 1 d . . . H10A H 0.3952 0.0491 0.2769 0.069 Uiso 1 1 calc R . . H10B H 0.4066 0.1867 0.2479 0.069 Uiso 1 1 calc R . . C1A C 0.8783(3) 0.4215(3) 0.0840(3) 0.0698(8) Uani 1 1 d . . . H1A1 H 0.9065 0.3701 0.0180 0.084 Uiso 1 1 calc R . . H1A2 H 0.8710 0.5028 0.0683 0.084 Uiso 1 1 calc R . . C2A C 1.0098(3) 0.4798(4) 0.2154(3) 0.0840(9) Uani 1 1 d . . . H2A1 H 1.0972 0.4548 0.2087 0.101 Uiso 1 1 calc R . . H2A2 H 1.0607 0.5870 0.2593 0.101 Uiso 1 1 calc R . . C3A C 0.9136(4) 0.4029(4) 0.2850(3) 0.0732(8) Uani 1 1 d . . . H3A H 0.9840 0.3847 0.3453 0.088 Uiso 1 1 calc R . . C4A C 0.8410(4) 0.4922(4) 0.3521(2) 0.0894(11) Uani 1 1 d . . . H4A1 H 0.7716 0.4361 0.3892 0.107 Uiso 1 1 calc R . . H4A2 H 0.9323 0.5847 0.4210 0.107 Uiso 1 1 calc R . . C5A C 0.7378(3) 0.5267(3) 0.2633(2) 0.0749(9) Uani 1 1 d . . . H5A1 H 0.6662 0.5538 0.3007 0.090 Uiso 1 1 calc R . . H5A2 H 0.8113 0.6107 0.2505 0.090 Uiso 1 1 calc R . . C6A C 0.4770(3) 0.3498(2) 0.07288(19) 0.0441(5) Uani 1 1 d . . . C7A C 0.4229(4) 0.2174(4) -0.0458(3) 0.0814(9) Uani 1 1 d . . . H7A1 H 0.3783 0.2312 -0.1205 0.098 Uiso 1 1 calc R . . H7A2 H 0.3364 0.1286 -0.0469 0.098 Uiso 1 1 calc R . . C8A C 0.5755(4) 0.2024(4) -0.0454(2) 0.0853(10) Uani 1 1 d . . . H8A1 H 0.6094 0.2239 -0.1127 0.102 Uiso 1 1 calc R . . H8A2 H 0.5526 0.1022 -0.0585 0.102 Uiso 1 1 calc R . . C9A C 0.7126(3) 0.3146(2) 0.08486(19) 0.0449(5) Uani 1 1 d . . . C10A C 0.7714(3) 0.2581(3) 0.1778(3) 0.0620(7) Uani 1 1 d . . . H10C H 0.8110 0.1914 0.1418 0.074 Uiso 1 1 calc R . . H10D H 0.6837 0.2081 0.2058 0.074 Uiso 1 1 calc R . . N1 N 0.2387(2) 0.0516(2) 0.43171(16) 0.0504(5) Uani 1 1 d . . . N1A N 0.6342(2) 0.3976(2) 0.14029(15) 0.0453(5) Uani 1 1 d . . . S1 S 0.26642(9) -0.06031(9) 0.60423(6) 0.0688(3) Uani 1 1 d . . . S1A S 0.35638(8) 0.41954(9) 0.11129(7) 0.0656(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0765(19) 0.0635(17) 0.109(2) 0.0424(17) 0.0506(18) 0.0448(16) C2 0.0587(18) 0.095(2) 0.109(2) 0.064(2) 0.0253(17) 0.0421(18) C3 0.0646(17) 0.087(2) 0.0441(12) 0.0224(13) 0.0094(12) 0.0379(16) C4 0.0684(18) 0.0573(17) 0.0624(16) 0.0084(13) -0.0036(14) 0.0262(15) C5 0.0519(15) 0.0542(16) 0.0675(16) 0.0281(13) 0.0040(13) 0.0082(13) C6 0.0481(13) 0.0581(15) 0.0412(11) 0.0156(10) 0.0207(10) 0.0288(12) C7 0.0591(17) 0.0717(18) 0.0544(14) 0.0148(13) 0.0128(13) 0.0226(15) C8 0.0658(18) 0.0598(17) 0.0579(15) 0.0138(13) 0.0226(14) 0.0062(14) C9 0.0489(13) 0.0438(13) 0.0484(12) 0.0169(10) 0.0220(11) 0.0184(11) C10 0.0561(15) 0.0779(17) 0.0487(12) 0.0264(12) 0.0251(12) 0.0383(14) C1A 0.0763(19) 0.0793(19) 0.0875(19) 0.0512(16) 0.0556(17) 0.0443(16) C2A 0.0464(16) 0.079(2) 0.122(3) 0.0329(19) 0.0366(18) 0.0303(15) C3A 0.0650(18) 0.098(2) 0.0611(15) 0.0359(16) 0.0100(14) 0.0491(18) C4A 0.0650(19) 0.125(3) 0.0433(14) 0.0085(16) 0.0085(13) 0.0405(19) C5A 0.0518(16) 0.0746(19) 0.0634(16) -0.0092(14) 0.0099(13) 0.0321(14) C6A 0.0444(13) 0.0492(13) 0.0430(11) 0.0243(10) 0.0172(10) 0.0230(11) C7A 0.0613(17) 0.087(2) 0.0555(15) -0.0037(14) 0.0068(13) 0.0312(16) C8A 0.091(2) 0.093(2) 0.0525(15) -0.0022(15) 0.0084(15) 0.060(2) C9A 0.0523(13) 0.0517(13) 0.0418(11) 0.0191(10) 0.0223(10) 0.0333(11) C10A 0.0619(16) 0.0632(16) 0.0812(17) 0.0445(14) 0.0305(14) 0.0370(14) N1 0.0476(11) 0.0467(11) 0.0439(10) 0.0190(8) 0.0133(9) 0.0136(9) N1A 0.0412(10) 0.0478(11) 0.0396(9) 0.0086(8) 0.0111(8) 0.0240(9) S1 0.0755(5) 0.0871(6) 0.0640(4) 0.0455(4) 0.0316(4) 0.0457(4) S1A 0.0537(4) 0.0861(5) 0.0742(4) 0.0361(4) 0.0292(3) 0.0451(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 C1 C2 1.528(4) . ? C1 C9 1.533(3) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 C3 1.519(4) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C10 1.525(3) . ? C3 C4 1.531(4) . ? C3 H3 0.9800 . ? C4 C5 1.498(4) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 N1 1.455(3) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 N1 1.309(3) . ? C6 C7 1.493(3) . ? C6 S1 1.669(2) . ? C7 C8 1.489(4) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.531(3) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 N1 1.478(3) . ? C9 C10 1.515(3) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C1A C2A 1.522(4) . ? C1A C9A 1.524(3) . ? C1A H1A1 0.9700 . ? C1A H1A2 0.9700 . ? C2A C3A 1.513(4) . ? C2A H2A1 0.9700 . ? C2A H2A2 0.9700 . ? C3A C10A 1.513(4) . ? C3A C4A 1.527(4) . ? C3A H3A 0.9800 . ? C4A C5A 1.499(4) . ? C4A H4A1 0.9700 . ? C4A H4A2 0.9700 . ? C5A N1A 1.463(3) . ? C5A H5A1 0.9700 . ? C5A H5A2 0.9700 . ? C6A N1A 1.312(3) . ? C6A C7A 1.491(3) . ? C6A S1A 1.658(2) . ? C7A C8A 1.500(4) . ? C7A H7A1 0.9700 . ? C7A H7A2 0.9700 . ? C8A C9A 1.523(3) . ? C8A H8A1 0.9700 . ? C8A H8A2 0.9700 . ? C9A N1A 1.471(3) . ? C9A C10A 1.505(3) . ? C10A H10C 0.9700 . ? C10A H10D 0.9700 . ? 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 C1 C9 105.6(2) . . ? C2 C1 H1A 110.6 . . ? C9 C1 H1A 110.6 . . ? C2 C1 H1B 110.6 . . ? C9 C1 H1B 110.6 . . ? H1A C1 H1B 108.7 . . ? C3 C2 C1 105.3(2) . . ? C3 C2 H2A 110.7 . . ? C1 C2 H2A 110.7 . . ? C3 C2 H2B 110.7 . . ? C1 C2 H2B 110.7 . . ? H2A C2 H2B 108.8 . . ? C2 C3 C10 102.4(2) . . ? C2 C3 C4 110.5(2) . . ? C10 C3 C4 109.1(2) . . ? C2 C3 H3 111.5 . . ? C10 C3 H3 111.5 . . ? C4 C3 H3 111.5 . . ? C5 C4 C3 112.0(2) . . ? C5 C4 H4A 109.2 . . ? C3 C4 H4A 109.2 . . ? C5 C4 H4B 109.2 . . ? C3 C4 H4B 109.2 . . ? H4A C4 H4B 107.9 . . ? N1 C5 C4 110.7(2) . . ? N1 C5 H5A 109.5 . . ? C4 C5 H5A 109.5 . . ? N1 C5 H5B 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 108.1 . . ? N1 C6 C7 108.1(2) . . ? N1 C6 S1 126.47(18) . . ? C7 C6 S1 125.47(18) . . ? C8 C7 C6 106.7(2) . . ? C8 C7 H7A 110.4 . . ? C6 C7 H7A 110.4 . . ? C8 C7 H7B 110.4 . . ? C6 C7 H7B 110.4 . . ? H7A C7 H7B 108.6 . . ? C7 C8 C9 106.3(2) . . ? C7 C8 H8A 110.5 . . ? C9 C8 H8A 110.5 . . ? C7 C8 H8B 110.5 . . ? C9 C8 H8B 110.5 . . ? H8A C8 H8B 108.7 . . ? N1 C9 C10 108.18(18) . . ? N1 C9 C8 102.01(18) . . ? C10 C9 C8 117.6(2) . . ? N1 C9 C1 109.24(19) . . ? C10 C9 C1 101.2(2) . . ? C8 C9 C1 118.3(2) . . ? C9 C10 C3 100.82(18) . . ? C9 C10 H10A 111.6 . . ? C3 C10 H10A 111.6 . . ? C9 C10 H10B 111.6 . . ? C3 C10 H10B 111.6 . . ? H10A C10 H10B 109.4 . . ? C2A C1A C9A 105.9(2) . . ? C2A C1A H1A1 110.5 . . ? C9A C1A H1A1 110.5 . . ? C2A C1A H1A2 110.5 . . ? C9A C1A H1A2 110.5 . . ? H1A1 C1A H1A2 108.7 . . ? C3A C2A C1A 104.6(2) . . ? C3A C2A H2A1 110.8 . . ? C1A C2A H2A1 110.8 . . ? C3A C2A H2A2 110.8 . . ? C1A C2A H2A2 110.8 . . ? H2A1 C2A H2A2 108.9 . . ? C2A C3A C10A 102.8(2) . . ? C2A C3A C4A 110.9(3) . . ? C10A C3A C4A 109.3(2) . . ? C2A C3A H3A 111.2 . . ? C10A C3A H3A 111.2 . . ? C4A C3A H3A 111.2 . . ? C5A C4A C3A 112.5(2) . . ? C5A C4A H4A1 109.1 . . ? C3A C4A H4A1 109.1 . . ? C5A C4A H4A2 109.1 . . ? C3A C4A H4A2 109.1 . . ? H4A1 C4A H4A2 107.8 . . ? N1A C5A C4A 110.4(2) . . ? N1A C5A H5A1 109.6 . . ? C4A C5A H5A1 109.6 . . ? N1A C5A H5A2 109.6 . . ? C4A C5A H5A2 109.6 . . ? H5A1 C5A H5A2 108.1 . . ? N1A C6A C7A 107.5(2) . . ? N1A C6A S1A 127.16(17) . . ? C7A C6A S1A 125.33(19) . . ? C6A C7A C8A 106.9(2) . . ? C6A C7A H7A1 110.3 . . ? C8A C7A H7A1 110.3 . . ? C6A C7A H7A2 110.3 . . ? C8A C7A H7A2 110.3 . . ? H7A1 C7A H7A2 108.6 . . ? C7A C8A C9A 106.2(2) . . ? C7A C8A H8A1 110.5 . . ? C9A C8A H8A1 110.5 . . ? C7A C8A H8A2 110.5 . . ? C9A C8A H8A2 110.5 . . ? H8A1 C8A H8A2 108.7 . . ? N1A C9A C10A 107.80(17) . . ? N1A C9A C8A 102.36(18) . . ? C10A C9A C8A 118.9(2) . . ? N1A C9A C1A 110.04(19) . . ? C10A C9A C1A 101.7(2) . . ? C8A C9A C1A 115.9(2) . . ? C9A C10A C3A 100.6(2) . . ? C9A C10A H10C 111.7 . . ? C3A C10A H10C 111.7 . . ? C9A C10A H10D 111.7 . . ? C3A C10A H10D 111.7 . . ? H10C C10A H10D 109.4 . . ? C6 N1 C5 126.12(19) . . ? C6 N1 C9 115.82(18) . . ? C5 N1 C9 117.96(18) . . ? C6A N1A C5A 125.86(19) . . ? C6A N1A C9A 116.40(17) . . ? C5A N1A C9A 117.73(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 C9 C1 C2 C3 -1.8(3) . . . . ? C1 C2 C3 C10 -27.5(3) . . . . ? C1 C2 C3 C4 88.6(3) . . . . ? C2 C3 C4 C5 -51.5(3) . . . . ? C10 C3 C4 C5 60.3(3) . . . . ? C3 C4 C5 N1 -42.9(3) . . . . ? N1 C6 C7 C8 6.2(3) . . . . ? S1 C6 C7 C8 -174.61(19) . . . . ? C6 C7 C8 C9 -10.0(3) . . . . ? C7 C8 C9 N1 9.8(3) . . . . ? C7 C8 C9 C10 -108.3(3) . . . . ? C7 C8 C9 C1 129.6(2) . . . . ? C2 C1 C9 N1 -83.5(2) . . . . ? C2 C1 C9 C10 30.5(2) . . . . ? C2 C1 C9 C8 160.5(2) . . . . ? N1 C9 C10 C3 67.4(2) . . . . ? C8 C9 C10 C3 -177.9(2) . . . . ? C1 C9 C10 C3 -47.4(2) . . . . ? C2 C3 C10 C9 46.8(3) . . . . ? C4 C3 C10 C9 -70.3(3) . . . . ? C9A C1A C2A C3A 0.4(3) . . . . ? C1A C2A C3A C10A 28.6(3) . . . . ? C1A C2A C3A C4A -88.1(3) . . . . ? C2A C3A C4A C5A 53.6(3) . . . . ? C10A C3A C4A C5A -59.0(3) . . . . ? C3A C4A C5A N1A 41.0(4) . . . . ? N1A C6A C7A C8A -5.5(3) . . . . ? S1A C6A C7A C8A 175.5(2) . . . . ? C6A C7A C8A C9A 8.2(3) . . . . ? C7A C8A C9A N1A -7.6(3) . . . . ? C7A C8A C9A C10A 111.0(3) . . . . ? C7A C8A C9A C1A -127.3(3) . . . . ? C2A C1A C9A N1A 84.8(2) . . . . ? C2A C1A C9A C10A -29.2(3) . . . . ? C2A C1A C9A C8A -159.7(2) . . . . ? N1A C9A C10A C3A -69.0(2) . . . . ? C8A C9A C10A C3A 175.3(2) . . . . ? C1A C9A C10A C3A 46.7(2) . . . . ? C2A C3A C10A C9A -47.1(3) . . . . ? C4A C3A C10A C9A 70.7(3) . . . . ? C7 C6 N1 C5 176.8(2) . . . . ? S1 C6 N1 C5 -2.4(3) . . . . ? C7 C6 N1 C9 0.4(3) . . . . ? S1 C6 N1 C9 -178.72(15) . . . . ? C4 C5 N1 C6 -132.5(2) . . . . ? C4 C5 N1 C9 43.7(3) . . . . ? C10 C9 N1 C6 118.0(2) . . . . ? C8 C9 N1 C6 -6.6(3) . . . . ? C1 C9 N1 C6 -132.6(2) . . . . ? C10 C9 N1 C5 -58.6(3) . . . . ? C8 C9 N1 C5 176.8(2) . . . . ? C1 C9 N1 C5 50.8(3) . . . . ? C7A C6A N1A C5A 179.2(3) . . . . ? S1A C6A N1A C5A -1.9(3) . . . . ? C7A C6A N1A C9A 0.4(3) . . . . ? S1A C6A N1A C9A 179.44(16) . . . . ? C4A C5A N1A C6A 138.3(2) . . . . ? C4A C5A N1A C9A -43.0(3) . . . . ? C10A C9A N1A C6A -121.5(2) . . . . ? C8A C9A N1A C6A 4.6(3) . . . . ? C1A C9A N1A C6A 128.4(2) . . . . ? C10A C9A N1A C5A 59.7(3) . . . . ? C8A C9A N1A C5A -174.2(2) . . . . ? C1A C9A N1A C5A -50.4(3) . . . . ? _diffrn_measured_fraction_theta_max 0.952 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.271 _refine_diff_density_min -0.231 _refine_diff_density_rms 0.041