# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Andrew Houlton' _publ_contact_author_email andrew.houlton@ncl.ac.uk loop_ _publ_author_name A.Houlton M.Galindo J.Hannant R.Harrington W.Clegg A.Pike data_ah128_compound_5 _database_code_depnum_ccdc_archive 'CCDC 785461' #TrackingRef 'OBC-Revised-CIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H11 N S2' _chemical_formula_sum 'C15 H11 N S2' _chemical_formula_weight 269.37 _chemical_absolute_configuration . 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 orthorhombic _symmetry_space_group_name_H-M 'P n a 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z+1/2' _cell_length_a 16.7710(16) _cell_length_b 7.1231(10) _cell_length_c 21.515(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2570.2(6) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 152 _cell_measurement_theta_min 2.50 _cell_measurement_theta_max 27.50 _exptl_crystal_description slab _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.392 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1120 _exptl_absorpt_coefficient_mu 0.393 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.860 _exptl_absorpt_correction_T_max 0.925 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'Nonius KappaCCD diffractometer' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 26623 _diffrn_reflns_av_R_equivalents 0.0594 _diffrn_reflns_av_sigmaI/netI 0.0544 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 4.21 _diffrn_reflns_theta_max 27.51 _reflns_number_total 5755 _reflns_number_gt 4538 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Nonius COLLECT' _computing_cell_refinement EvalCCD _computing_data_reduction EvalCCD _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL and local programs' _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^)+(0.0764P)^2^+2.3868P] 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 0.0030(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.10(10) _refine_ls_number_reflns 5755 _refine_ls_number_parameters 327 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0826 _refine_ls_R_factor_gt 0.0554 _refine_ls_wR_factor_ref 0.1480 _refine_ls_wR_factor_gt 0.1307 _refine_ls_goodness_of_fit_ref 1.086 _refine_ls_restrained_S_all 1.086 _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 0.68676(6) 0.39961(15) 0.78301(5) 0.0283(3) Uani 1 1 d . . . S2 S 1.04085(7) -0.22489(18) 0.85582(5) 0.0339(3) Uani 1 1 d . . . S3 S 1.27392(7) -0.23771(16) 0.91176(6) 0.0312(3) Uani 1 1 d . . . S4 S 0.92670(6) 0.39934(15) 0.98377(5) 0.0287(3) Uani 1 1 d . . . N1 N 0.84904(17) -0.0106(5) 0.76745(14) 0.0190(7) Uani 1 1 d . . . N2 N 1.08715(18) -0.0124(4) 1.00272(13) 0.0178(7) Uani 1 1 d . . . C1 C 0.6285(2) 0.4321(6) 0.7180(2) 0.0275(9) Uani 1 1 d . . . H1 H 0.5844 0.5156 0.7159 0.033 Uiso 1 1 calc R . . C2 C 0.6540(3) 0.3218(6) 0.6697(2) 0.0300(10) Uani 1 1 d . . . H2 H 0.6287 0.3188 0.6302 0.036 Uiso 1 1 calc R . . C3 C 0.7222(2) 0.2125(7) 0.6848(2) 0.0252(9) Uani 1 1 d . . . H3 H 0.7475 0.1295 0.6564 0.030 Uiso 1 1 calc R . . C4 C 0.7475(2) 0.2397(5) 0.74513(19) 0.0200(8) Uani 1 1 d . . . C5 C 0.8197(2) 0.1696(5) 0.77605(18) 0.0214(8) Uani 1 1 d . . . C6 C 0.8742(2) 0.2659(6) 0.8128(2) 0.0229(9) Uani 1 1 d . . . H6 H 0.8687 0.3913 0.8272 0.028 Uiso 1 1 calc R . . C7 C 0.9385(2) 0.1458(6) 0.82484(18) 0.0242(9) Uani 1 1 d . . . H7 H 0.9850 0.1768 0.8479 0.029 Uiso 1 1 calc R . . C8 C 0.9226(2) -0.0261(6) 0.79726(17) 0.0202(8) Uani 1 1 d . . . C9 C 0.9727(2) -0.1920(6) 0.79527(18) 0.0222(9) Uani 1 1 d . . . C10 C 0.9838(2) -0.3273(5) 0.7499(2) 0.0236(8) Uani 1 1 d . . . H10 H 0.9527 -0.3350 0.7130 0.028 Uiso 1 1 calc R . . C11 C 1.0474(2) -0.4548(6) 0.7646(2) 0.0292(10) Uani 1 1 d . . . H11 H 1.0625 -0.5566 0.7386 0.035 Uiso 1 1 calc R . . C12 C 1.0841(3) -0.4146(7) 0.8198(2) 0.0334(11) Uani 1 1 d . . . H12 H 1.1279 -0.4830 0.8362 0.040 Uiso 1 1 calc R . . C13 C 0.8028(2) -0.1687(6) 0.74269(18) 0.0208(8) Uani 1 1 d . . . H13A H 0.7455 -0.1428 0.7494 0.025 Uiso 1 1 calc R . . H13B H 0.8165 -0.2827 0.7668 0.025 Uiso 1 1 calc R . . C14 C 0.8154(2) -0.2087(6) 0.67598(19) 0.0225(8) Uani 1 1 d . . . C15 C 0.8247(3) -0.2406(7) 0.6226(2) 0.0318(11) Uani 1 1 d . . . H15 H 0.8322 -0.2663 0.5796 0.038 Uiso 1 1 calc R . . C16 C 1.3165(2) -0.4283(7) 0.9474(2) 0.0308(10) Uani 1 1 d . . . H16 H 1.3580 -0.5013 0.9297 0.037 Uiso 1 1 calc R . . C17 C 1.2840(2) -0.4624(6) 1.0038(2) 0.0297(10) Uani 1 1 d . . . H17 H 1.3000 -0.5631 1.0299 0.036 Uiso 1 1 calc R . . C18 C 1.2233(2) -0.3311(6) 1.01984(19) 0.0215(8) Uani 1 1 d . . . H18 H 1.1947 -0.3346 1.0580 0.026 Uiso 1 1 calc R . . C19 C 1.2102(2) -0.1984(6) 0.97425(18) 0.0199(8) Uani 1 1 d . . . C20 C 1.1614(2) -0.0270(6) 0.97403(16) 0.0186(7) Uani 1 1 d . . . C21 C 1.1788(2) 0.1425(6) 0.94699(18) 0.0226(8) Uani 1 1 d . . . H21 H 1.2254 0.1723 0.9239 0.027 Uiso 1 1 calc R . . C22 C 1.1148(2) 0.2638(6) 0.95982(19) 0.0221(9) Uani 1 1 d . . . H22 H 1.1110 0.3910 0.9468 0.027 Uiso 1 1 calc R . . C23 C 1.0588(2) 0.1693(5) 0.99409(17) 0.0199(8) Uani 1 1 d . . . C24 C 0.9867(2) 0.2398(5) 1.0233(2) 0.0214(9) Uani 1 1 d . . . C25 C 0.9594(2) 0.2174(7) 1.0839(2) 0.0245(9) Uani 1 1 d . . . H25 H 0.9840 0.1365 1.1134 0.029 Uiso 1 1 calc R . . C26 C 0.8910(2) 0.3285(7) 1.0972(2) 0.0288(9) Uani 1 1 d . . . H26 H 0.8645 0.3284 1.1363 0.035 Uiso 1 1 calc R . . C27 C 0.8672(2) 0.4361(6) 1.0473(2) 0.0297(10) Uani 1 1 d . . . H27 H 0.8232 0.5201 1.0481 0.036 Uiso 1 1 calc R . . C28 C 1.0401(2) -0.1699(6) 1.02728(18) 0.0213(8) Uani 1 1 d . . . H28A H 1.0535 -0.2843 1.0033 0.026 Uiso 1 1 calc R . . H28B H 0.9828 -0.1430 1.0204 0.026 Uiso 1 1 calc R . . C29 C 1.0526(2) -0.2088(6) 1.0941(2) 0.0243(9) Uani 1 1 d . . . C30 C 1.0622(3) -0.2409(6) 1.1479(3) 0.0312(11) Uani 1 1 d . . . H30 H 1.0699 -0.2665 1.1909 0.037 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 0.0308(5) 0.0267(6) 0.0275(5) -0.0045(5) 0.0036(4) 0.0041(4) S2 0.0343(6) 0.0446(7) 0.0227(6) 0.0014(5) -0.0054(5) 0.0086(5) S3 0.0356(6) 0.0358(6) 0.0222(6) -0.0001(5) 0.0090(5) 0.0076(5) S4 0.0292(5) 0.0247(6) 0.0322(6) 0.0009(5) -0.0064(4) 0.0066(4) N1 0.0173(15) 0.0203(17) 0.0194(17) 0.0012(12) 0.0003(12) -0.0040(13) N2 0.0191(15) 0.0187(17) 0.0155(15) 0.0006(12) -0.0005(11) -0.0004(13) C1 0.023(2) 0.028(2) 0.031(2) 0.0060(19) 0.0037(17) 0.0058(17) C2 0.029(2) 0.034(3) 0.027(2) 0.0020(19) -0.0030(18) 0.0037(19) C3 0.023(2) 0.027(2) 0.026(2) -0.0015(19) 0.0016(16) 0.0037(17) C4 0.0233(19) 0.019(2) 0.017(2) 0.0003(15) 0.0032(15) -0.0004(16) C5 0.0213(18) 0.023(2) 0.0193(19) -0.0025(16) 0.0033(15) -0.0010(15) C6 0.029(2) 0.019(2) 0.021(2) -0.0044(15) -0.0006(16) -0.0007(17) C7 0.025(2) 0.027(2) 0.021(2) -0.0034(16) -0.0016(16) -0.0053(17) C8 0.0193(18) 0.021(2) 0.0199(19) 0.0021(15) -0.0001(14) -0.0040(15) C9 0.0193(19) 0.026(2) 0.022(2) 0.0065(18) 0.0021(15) -0.0050(15) C10 0.0212(19) 0.020(2) 0.030(2) -0.0011(17) 0.0003(17) -0.0022(16) C11 0.027(2) 0.020(2) 0.041(3) 0.0007(18) 0.0035(18) 0.0002(17) C12 0.030(2) 0.032(3) 0.038(3) 0.012(2) 0.0025(19) 0.0069(19) C13 0.0201(18) 0.023(2) 0.0197(19) 0.0003(16) -0.0009(15) -0.0069(16) C14 0.0166(18) 0.024(2) 0.027(2) -0.0066(18) -0.0026(16) -0.0008(16) C15 0.030(2) 0.041(3) 0.024(3) -0.0075(19) -0.0026(18) -0.001(2) C16 0.023(2) 0.032(2) 0.037(3) -0.003(2) 0.0021(18) 0.0078(18) C17 0.027(2) 0.024(2) 0.038(3) 0.0027(19) -0.0035(18) 0.0025(18) C18 0.0189(18) 0.025(2) 0.0211(19) 0.0004(16) 0.0022(15) -0.0017(16) C19 0.0197(18) 0.023(2) 0.017(2) -0.0035(17) 0.0016(15) -0.0014(15) C20 0.0182(17) 0.0240(19) 0.0136(17) -0.0028(15) 0.0014(14) -0.0007(15) C21 0.022(2) 0.028(2) 0.0169(18) 0.0009(16) 0.0031(15) -0.0052(17) C22 0.032(2) 0.019(2) 0.015(2) 0.0036(14) -0.0026(15) 0.0005(17) C23 0.0226(19) 0.0173(19) 0.0199(19) -0.0014(15) -0.0048(15) 0.0025(15) C24 0.0223(19) 0.017(2) 0.025(2) -0.0014(15) -0.0020(16) 0.0004(16) C25 0.024(2) 0.030(2) 0.019(2) -0.0010(19) -0.0018(15) 0.0059(17) C26 0.024(2) 0.033(3) 0.029(2) -0.005(2) 0.0020(17) 0.0040(18) C27 0.022(2) 0.025(2) 0.042(3) -0.014(2) -0.0039(18) 0.0090(17) C28 0.0165(18) 0.021(2) 0.027(2) 0.0025(16) 0.0020(15) -0.0004(15) C29 0.0211(19) 0.021(2) 0.031(2) 0.0017(18) 0.0043(17) -0.0037(17) C30 0.033(2) 0.032(3) 0.028(3) 0.0070(18) 0.0003(19) -0.014(2) _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 1.722(4) . ? S1 C4 1.732(4) . ? S2 C9 1.749(4) . ? S2 C12 1.718(5) . ? S3 C16 1.715(5) . ? S3 C19 1.740(4) . ? S4 C24 1.740(4) . ? S4 C27 1.713(5) . ? N1 C5 1.387(5) . ? N1 C8 1.394(5) . ? N1 C13 1.467(5) . ? N2 C20 1.394(5) . ? N2 C23 1.391(5) . ? N2 C28 1.470(5) . ? C1 H1 0.950 . ? C1 C2 1.371(6) . ? C2 H2 0.950 . ? C2 C3 1.421(6) . ? C3 H3 0.950 . ? C3 C4 1.379(6) . ? C4 C5 1.469(6) . ? C5 C6 1.389(6) . ? C6 H6 0.950 . ? C6 C7 1.401(6) . ? C7 H7 0.950 . ? C7 C8 1.387(6) . ? C8 C9 1.451(6) . ? C9 C10 1.385(6) . ? C10 H10 0.950 . ? C10 C11 1.437(6) . ? C11 H11 0.950 . ? C11 C12 1.369(7) . ? C12 H12 0.950 . ? C13 H13A 0.990 . ? C13 H13B 0.990 . ? C13 C14 1.479(6) . ? C14 C15 1.182(6) . ? C15 H15 0.950 . ? C16 H16 0.950 . ? C16 C17 1.350(6) . ? C17 H17 0.950 . ? C17 C18 1.426(6) . ? C18 H18 0.950 . ? C18 C19 1.380(6) . ? C19 C20 1.470(6) . ? C20 C21 1.371(6) . ? C21 H21 0.950 . ? C21 C22 1.406(6) . ? C22 H22 0.950 . ? C22 C23 1.371(6) . ? C23 C24 1.452(6) . ? C24 C25 1.392(6) . ? C25 H25 0.950 . ? C25 C26 1.423(6) . ? C26 H26 0.950 . ? C26 C27 1.378(7) . ? C27 H27 0.950 . ? C28 H28A 0.990 . ? C28 H28B 0.990 . ? C28 C29 1.478(6) . ? C29 C30 1.193(7) . ? C30 H30 0.950 . ? 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 C4 92.3(2) . . ? C9 S2 C12 92.6(2) . . ? C16 S3 C19 92.1(2) . . ? C24 S4 C27 92.7(2) . . ? C5 N1 C8 109.0(3) . . ? C5 N1 C13 124.8(3) . . ? C8 N1 C13 125.0(3) . . ? C20 N2 C23 108.4(3) . . ? C20 N2 C28 125.6(3) . . ? C23 N2 C28 125.1(3) . . ? S1 C1 H1 124.4 . . ? S1 C1 C2 111.2(3) . . ? H1 C1 C2 124.4 . . ? C1 C2 H2 123.5 . . ? C1 C2 C3 113.0(4) . . ? H2 C2 C3 123.5 . . ? C2 C3 H3 123.6 . . ? C2 C3 C4 112.7(4) . . ? H3 C3 C4 123.6 . . ? S1 C4 C3 110.7(3) . . ? S1 C4 C5 119.7(3) . . ? C3 C4 C5 129.2(4) . . ? N1 C5 C4 123.1(3) . . ? N1 C5 C6 107.5(3) . . ? C4 C5 C6 129.2(4) . . ? C5 C6 H6 126.0 . . ? C5 C6 C7 108.1(4) . . ? H6 C6 C7 126.0 . . ? C6 C7 H7 125.9 . . ? C6 C7 C8 108.2(4) . . ? H7 C7 C8 125.9 . . ? N1 C8 C7 107.3(3) . . ? N1 C8 C9 124.3(3) . . ? C7 C8 C9 128.3(3) . . ? S2 C9 C8 117.8(3) . . ? S2 C9 C10 110.2(3) . . ? C8 C9 C10 131.7(4) . . ? C9 C10 H10 123.7 . . ? C9 C10 C11 112.6(4) . . ? H10 C10 C11 123.7 . . ? C10 C11 H11 123.4 . . ? C10 C11 C12 113.2(4) . . ? H11 C11 C12 123.4 . . ? S2 C12 C11 111.5(3) . . ? S2 C12 H12 124.3 . . ? C11 C12 H12 124.3 . . ? N1 C13 H13A 108.5 . . ? N1 C13 H13B 108.5 . . ? N1 C13 C14 115.2(3) . . ? H13A C13 H13B 107.5 . . ? H13A C13 C14 108.5 . . ? H13B C13 C14 108.5 . . ? C13 C14 C15 179.4(4) . . ? C14 C15 H15 180.0 . . ? S3 C16 H16 123.9 . . ? S3 C16 C17 112.1(3) . . ? H16 C16 C17 123.9 . . ? C16 C17 H17 123.6 . . ? C16 C17 C18 112.8(4) . . ? H17 C17 C18 123.6 . . ? C17 C18 H18 123.5 . . ? C17 C18 C19 113.0(4) . . ? H18 C18 C19 123.5 . . ? S3 C19 C18 110.0(3) . . ? S3 C19 C20 118.2(3) . . ? C18 C19 C20 131.3(4) . . ? N2 C20 C19 123.9(3) . . ? N2 C20 C21 108.2(3) . . ? C19 C20 C21 127.9(3) . . ? C20 C21 H21 126.4 . . ? C20 C21 C22 107.2(3) . . ? H21 C21 C22 126.4 . . ? C21 C22 H22 125.5 . . ? C21 C22 C23 109.1(4) . . ? H22 C22 C23 125.5 . . ? N2 C23 C22 107.1(3) . . ? N2 C23 C24 123.3(3) . . ? C22 C23 C24 129.3(4) . . ? S4 C24 C23 119.8(3) . . ? S4 C24 C25 110.1(3) . . ? C23 C24 C25 129.7(4) . . ? C24 C25 H25 123.5 . . ? C24 C25 C26 112.9(4) . . ? H25 C25 C26 123.5 . . ? C25 C26 H26 123.6 . . ? C25 C26 C27 112.7(4) . . ? H26 C26 C27 123.6 . . ? S4 C27 C26 111.6(3) . . ? S4 C27 H27 124.2 . . ? C26 C27 H27 124.2 . . ? N2 C28 H28A 108.6 . . ? N2 C28 H28B 108.6 . . ? N2 C28 C29 114.6(3) . . ? H28A C28 H28B 107.6 . . ? H28A C28 C29 108.6 . . ? H28B C28 C29 108.6 . . ? C28 C29 C30 179.5(5) . . ? C29 C30 H30 180.0 . . ? 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 C4 S1 C1 C2 1.1(4) . . . . ? S1 C1 C2 C3 -1.1(5) . . . . ? C1 C2 C3 C4 0.6(6) . . . . ? C2 C3 C4 S1 0.3(5) . . . . ? C2 C3 C4 C5 -172.7(4) . . . . ? C1 S1 C4 C3 -0.8(3) . . . . ? C1 S1 C4 C5 173.0(3) . . . . ? C8 N1 C5 C4 173.2(4) . . . . ? C8 N1 C5 C6 -1.5(4) . . . . ? C13 N1 C5 C4 -18.7(5) . . . . ? C13 N1 C5 C6 166.6(3) . . . . ? S1 C4 C5 N1 146.9(3) . . . . ? S1 C4 C5 C6 -39.6(6) . . . . ? C3 C4 C5 N1 -40.7(6) . . . . ? C3 C4 C5 C6 132.8(5) . . . . ? N1 C5 C6 C7 2.1(4) . . . . ? C4 C5 C6 C7 -172.2(4) . . . . ? C5 C6 C7 C8 -1.9(5) . . . . ? C6 C7 C8 N1 0.9(4) . . . . ? C6 C7 C8 C9 177.7(4) . . . . ? C5 N1 C8 C7 0.4(4) . . . . ? C5 N1 C8 C9 -176.5(3) . . . . ? C13 N1 C8 C7 -167.8(3) . . . . ? C13 N1 C8 C9 15.3(6) . . . . ? N1 C8 C9 S2 -156.2(3) . . . . ? N1 C8 C9 C10 31.5(6) . . . . ? C7 C8 C9 S2 27.6(5) . . . . ? C7 C8 C9 C10 -144.7(4) . . . . ? C12 S2 C9 C8 -173.0(3) . . . . ? C12 S2 C9 C10 0.9(3) . . . . ? S2 C9 C10 C11 -0.3(4) . . . . ? C8 C9 C10 C11 172.4(4) . . . . ? C9 C10 C11 C12 -0.6(5) . . . . ? C10 C11 C12 S2 1.3(5) . . . . ? C9 S2 C12 C11 -1.3(4) . . . . ? C5 N1 C13 C14 99.0(4) . . . . ? C8 N1 C13 C14 -94.7(4) . . . . ? C19 S3 C16 C17 0.4(4) . . . . ? S3 C16 C17 C18 -0.6(5) . . . . ? C16 C17 C18 C19 0.5(5) . . . . ? C17 C18 C19 S3 -0.1(4) . . . . ? C17 C18 C19 C20 -171.6(4) . . . . ? C16 S3 C19 C18 -0.1(3) . . . . ? C16 S3 C19 C20 172.6(3) . . . . ? C23 N2 C20 C19 179.1(3) . . . . ? C23 N2 C20 C21 -0.9(4) . . . . ? C28 N2 C20 C19 -11.6(5) . . . . ? C28 N2 C20 C21 168.4(3) . . . . ? S3 C19 C20 N2 150.9(3) . . . . ? S3 C19 C20 C21 -29.2(5) . . . . ? C18 C19 C20 N2 -38.2(6) . . . . ? C18 C19 C20 C21 141.7(4) . . . . ? N2 C20 C21 C22 0.7(4) . . . . ? C19 C20 C21 C22 -179.3(4) . . . . ? C20 C21 C22 C23 -0.2(4) . . . . ? C21 C22 C23 N2 -0.3(4) . . . . ? C21 C22 C23 C24 173.4(4) . . . . ? C20 N2 C23 C22 0.7(4) . . . . ? C20 N2 C23 C24 -173.4(3) . . . . ? C28 N2 C23 C22 -168.6(3) . . . . ? C28 N2 C23 C24 17.2(6) . . . . ? N2 C23 C24 S4 -145.5(3) . . . . ? N2 C23 C24 C25 43.0(6) . . . . ? C22 C23 C24 S4 41.7(6) . . . . ? C22 C23 C24 C25 -129.8(5) . . . . ? C27 S4 C24 C23 -172.6(3) . . . . ? C27 S4 C24 C25 0.4(3) . . . . ? S4 C24 C25 C26 0.1(5) . . . . ? C23 C24 C25 C26 172.3(4) . . . . ? C24 C25 C26 C27 -0.8(6) . . . . ? C25 C26 C27 S4 1.1(5) . . . . ? C24 S4 C27 C26 -0.9(4) . . . . ? C20 N2 C28 C29 93.7(4) . . . . ? C23 N2 C28 C29 -98.8(4) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 1.047 _refine_diff_density_min -0.375 _refine_diff_density_rms 0.098 #===END data_ah185_compound_6 _database_code_depnum_ccdc_archive 'CCDC 785462' #TrackingRef 'OBC-Revised-CIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H13 N S2' _chemical_formula_sum 'C16 H13 N S2' _chemical_formula_weight 283.39 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/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 18.3919(5) _cell_length_b 16.7137(5) _cell_length_c 9.2800(3) _cell_angle_alpha 90.00 _cell_angle_beta 103.914(3) _cell_angle_gamma 90.00 _cell_volume 2768.94(14) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4545 _cell_measurement_theta_min 2.47 _cell_measurement_theta_max 62.23 _exptl_crystal_description lath _exptl_crystal_colour colourless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.360 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1184 _exptl_absorpt_coefficient_mu 3.340 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.585 _exptl_absorpt_correction_T_max 0.965 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'sealed tube with Enhance Ultra optics' _diffrn_radiation_monochromator none _diffrn_measurement_device_type 'Oxford Diffraction Gemini A Ultra diffractometer' _diffrn_measurement_method 'thick-slice \w scans' _diffrn_detector_area_resol_mean 10.3968 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8695 _diffrn_reflns_av_R_equivalents 0.0278 _diffrn_reflns_av_sigmaI/netI 0.0313 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.47 _diffrn_reflns_theta_max 62.30 _reflns_number_total 4288 _reflns_number_gt 3344 _reflns_threshold_expression I>2\s(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL and local programs' _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^)+(0.0700P)^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 4288 _refine_ls_number_parameters 431 _refine_ls_number_restraints 656 _refine_ls_R_factor_all 0.0535 _refine_ls_R_factor_gt 0.0389 _refine_ls_wR_factor_ref 0.1103 _refine_ls_wR_factor_gt 0.1038 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.057 _refine_ls_shift/su_max 0.030 _refine_ls_shift/su_mean 0.001 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 N1 N 0.36954(9) 0.73892(11) 0.58923(19) 0.0229(4) Uani 1 1 d . A . S1 S 0.44635(5) 0.92395(6) 0.60128(15) 0.0297(3) Uani 0.805(3) 1 d PDU A 1 C1 C 0.4183(2) 1.0215(2) 0.6148(6) 0.0308(9) Uani 0.805(3) 1 d PDU A 1 H1 H 0.4516 1.0656 0.6377 0.037 Uiso 0.805(3) 1 calc PR A 1 C2 C 0.3412(2) 1.0275(2) 0.5881(6) 0.0315(9) Uani 0.805(3) 1 d PDU A 1 H2 H 0.3142 1.0760 0.5883 0.038 Uiso 0.805(3) 1 calc PR A 1 C3 C 0.3083(5) 0.9505(6) 0.5606(18) 0.0358(17) Uani 0.805(3) 1 d PDU A 1 H3 H 0.2557 0.9427 0.5409 0.043 Uiso 0.805(3) 1 calc PR A 1 S1X S 0.2950(5) 0.9599(6) 0.565(2) 0.0389(17) Uani 0.195(3) 1 d PDU A 2 C1X C 0.3605(9) 1.0339(10) 0.606(3) 0.034(3) Uiso 0.195(3) 1 d PDU A 2 H1X H 0.3496 1.0885 0.6191 0.040 Uiso 0.195(3) 1 calc PR A 2 C2X C 0.4309(10) 1.0039(10) 0.617(3) 0.030(3) Uiso 0.195(3) 1 d PDU A 2 H2X H 0.4756 1.0349 0.6371 0.036 Uiso 0.195(3) 1 calc PR A 2 C3X C 0.4276(8) 0.9196(11) 0.595(3) 0.035(4) Uiso 0.195(3) 1 d PDU A 2 H3X H 0.4707 0.8874 0.6005 0.042 Uiso 0.195(3) 1 calc PR A 2 C4 C 0.35635(11) 0.88904(14) 0.5640(2) 0.0251(5) Uani 1 1 d DU . . C5 C 0.33637(11) 0.80695(14) 0.5170(2) 0.0234(5) Uani 1 1 d . A . C6 C 0.28405(11) 0.78241(15) 0.3921(2) 0.0265(5) Uani 1 1 d . . . H6 H 0.2524 0.8163 0.3219 0.032 Uiso 1 1 calc R A . C7 C 0.28572(11) 0.69863(15) 0.3871(2) 0.0266(5) Uani 1 1 d . A . H7 H 0.2556 0.6658 0.3125 0.032 Uiso 1 1 calc R . . C8 C 0.33881(11) 0.67209(14) 0.5095(2) 0.0238(5) Uani 1 1 d . . . C9 C 0.36075(11) 0.58988(14) 0.5540(2) 0.0253(5) Uani 1 1 d DU A . C10 C 0.3934(7) 0.5367(6) 0.4838(10) 0.0421(18) Uani 0.797(3) 1 d PDU A 1 H10 H 0.4105 0.5510 0.3986 0.050 Uiso 0.797(3) 1 calc PR A 1 C11 C 0.4017(4) 0.4565(3) 0.5423(6) 0.0302(10) Uani 0.797(3) 1 d PDU A 1 H11 H 0.4205 0.4118 0.4995 0.036 Uiso 0.797(3) 1 calc PR A 1 C12 C 0.3771(4) 0.4563(3) 0.6727(7) 0.0325(11) Uani 0.797(3) 1 d PDU A 1 H12 H 0.3799 0.4108 0.7353 0.039 Uiso 0.797(3) 1 calc PR A 1 S2 S 0.34123(6) 0.54669(6) 0.70859(11) 0.0326(3) Uani 0.797(3) 1 d PDU A 1 C10X C 0.3554(12) 0.5541(10) 0.6828(18) 0.038(4) Uiso 0.203(3) 1 d PDU A 2 H10X H 0.3426 0.5821 0.7623 0.046 Uiso 0.203(3) 1 calc PR A 2 C11X C 0.3712(19) 0.4701(11) 0.687(3) 0.028(3) Uiso 0.203(3) 1 d PDU A 2 H11X H 0.3610 0.4329 0.7567 0.033 Uiso 0.203(3) 1 calc PR A 2 C12X C 0.404(2) 0.4523(12) 0.571(2) 0.030(3) Uiso 0.203(3) 1 d PDU A 2 H12X H 0.4269 0.4027 0.5582 0.036 Uiso 0.203(3) 1 calc PR A 2 S2X S 0.3968(8) 0.5324(6) 0.4530(11) 0.0402(16) Uani 0.203(3) 1 d PDU A 2 C13 C 0.43187(11) 0.73755(14) 0.7201(2) 0.0238(5) Uani 1 1 d . . . H13A H 0.4243 0.6938 0.7869 0.029 Uiso 1 1 calc R A . H13B H 0.4335 0.7887 0.7745 0.029 Uiso 1 1 calc R . . C14 C 0.50646(11) 0.72497(15) 0.6768(2) 0.0284(5) Uani 1 1 d . A . H14A H 0.5071 0.6708 0.6341 0.034 Uiso 1 1 calc R . . H14B H 0.5106 0.7643 0.5995 0.034 Uiso 1 1 calc R . . C15 C 0.57116(12) 0.73378(14) 0.8043(3) 0.0296(5) Uani 1 1 d . . . C16 C 0.62273(13) 0.74201(16) 0.9073(3) 0.0385(6) Uani 1 1 d . A . H16 H 0.6642 0.7486 0.9900 0.046 Uiso 1 1 calc R . . N2 N 0.12744(9) 0.24492(12) 0.3807(2) 0.0263(4) Uani 1 1 d . B . S3 S 0.20343(5) 0.47013(7) 0.38317(13) 0.0343(3) Uani 0.759(3) 1 d PDU B 1 C17 C 0.1382(2) 0.5437(3) 0.3826(7) 0.0369(11) Uani 0.759(3) 1 d PDU B 1 H17 H 0.1496 0.5992 0.3935 0.044 Uiso 0.759(3) 1 calc PR B 1 C18 C 0.0676(3) 0.5125(3) 0.3644(10) 0.0352(11) Uani 0.759(3) 1 d PDU B 1 H18 H 0.0237 0.5432 0.3611 0.042 Uiso 0.759(3) 1 calc PR B 1 C19 C 0.0691(4) 0.4284(6) 0.3512(16) 0.0388(18) Uani 0.759(3) 1 d PDU B 1 H19 H 0.0248 0.3970 0.3353 0.047 Uiso 0.759(3) 1 calc PR B 1 S3X S 0.0531(4) 0.4230(5) 0.3572(15) 0.0416(15) Uani 0.241(3) 1 d PDU B 2 C17X C 0.0775(10) 0.5215(9) 0.382(4) 0.035(3) Uiso 0.241(3) 1 d PDU B 2 H17X H 0.0434 0.5637 0.3853 0.042 Uiso 0.241(3) 1 calc PR B 2 C18X C 0.1538(9) 0.5317(9) 0.395(3) 0.035(3) Uiso 0.241(3) 1 d PDU B 2 H18X H 0.1790 0.5817 0.4027 0.043 Uiso 0.241(3) 1 calc PR B 2 C19X C 0.1881(8) 0.4552(8) 0.396(2) 0.043(3) Uiso 0.241(3) 1 d PDU B 2 H19X H 0.2408 0.4476 0.4176 0.052 Uiso 0.241(3) 1 calc PR B 2 C20 C 0.13819(12) 0.39483(15) 0.3626(2) 0.0302(5) Uani 1 1 d DU . . C21 C 0.16072(11) 0.31309(15) 0.3404(2) 0.0285(5) Uani 1 1 d . B . C22 C 0.21632(12) 0.28806(17) 0.2732(3) 0.0342(6) Uani 1 1 d . . . H22 H 0.2486 0.3219 0.2347 0.041 Uiso 1 1 calc R B . C23 C 0.21676(12) 0.20473(17) 0.2717(3) 0.0343(6) Uani 1 1 d . B . H23 H 0.2494 0.1720 0.2320 0.041 Uiso 1 1 calc R . . C24 C 0.16123(11) 0.17773(15) 0.3381(2) 0.0292(6) Uani 1 1 d . . . C25 C 0.13929(12) 0.09460(16) 0.3518(2) 0.0309(6) Uani 1 1 d DU B . C26 C 0.1463(8) 0.0382(6) 0.2566(13) 0.0383(18) Uani 0.782(3) 1 d PDU B 1 H26 H 0.1635 0.0491 0.1699 0.046 Uiso 0.782(3) 1 calc PR B 1 C27 C 0.1263(3) -0.0408(3) 0.2935(5) 0.0316(9) Uani 0.782(3) 1 d PDU B 1 H27 H 0.1300 -0.0876 0.2374 0.038 Uiso 0.782(3) 1 calc PR B 1 C28 C 0.1007(2) -0.0396(2) 0.4227(5) 0.0338(10) Uani 0.782(3) 1 d PDU B 1 H28 H 0.0838 -0.0851 0.4667 0.041 Uiso 0.782(3) 1 calc PR B 1 S4 S 0.10381(7) 0.05593(7) 0.49110(12) 0.0343(3) Uani 0.782(3) 1 d PDU B 1 C26X C 0.1186(12) 0.0617(10) 0.4713(19) 0.040(4) Uiso 0.218(3) 1 d PDU B 2 H26X H 0.1141 0.0921 0.5552 0.048 Uiso 0.218(3) 1 calc PR B 2 C27X C 0.1041(12) -0.0232(9) 0.4584(18) 0.034(3) Uiso 0.218(3) 1 d PDU B 2 H27X H 0.0857 -0.0546 0.5274 0.041 Uiso 0.218(3) 1 calc PR B 2 C28X C 0.1207(12) -0.0516(9) 0.3320(18) 0.031(3) Uiso 0.218(3) 1 d PDU B 2 H28X H 0.1163 -0.1059 0.3009 0.037 Uiso 0.218(3) 1 calc PR B 2 S4X S 0.1505(9) 0.0249(6) 0.2375(12) 0.0436(17) Uani 0.218(3) 1 d PDU B 2 C29 C 0.06371(11) 0.24482(15) 0.4487(2) 0.0266(5) Uani 1 1 d . . . H29A H 0.0610 0.2969 0.4982 0.032 Uiso 1 1 calc R B . H29B H 0.0705 0.2023 0.5251 0.032 Uiso 1 1 calc R . . C30 C -0.00952(11) 0.23042(16) 0.3313(3) 0.0302(6) Uani 1 1 d . B . H30A H -0.0129 0.2688 0.2488 0.036 Uiso 1 1 calc R . . H30B H -0.0089 0.1758 0.2905 0.036 Uiso 1 1 calc R . . C31 C -0.07585(13) 0.23941(15) 0.3922(3) 0.0311(6) Uani 1 1 d . . . C32 C -0.12887(14) 0.24620(16) 0.4416(3) 0.0401(6) Uani 1 1 d . B . H32 H -0.1716 0.2517 0.4815 0.048 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 N1 0.0186(9) 0.0277(11) 0.0224(9) -0.0015(8) 0.0047(7) -0.0002(8) S1 0.0211(5) 0.0309(5) 0.0382(5) -0.0032(3) 0.0090(4) -0.0067(4) C1 0.041(2) 0.0220(19) 0.0341(17) -0.0036(19) 0.0179(18) -0.0023(17) C2 0.032(2) 0.0307(17) 0.032(2) 0.0007(14) 0.0068(19) 0.0018(15) C3 0.030(3) 0.041(3) 0.034(3) -0.001(3) 0.005(3) 0.005(2) S1X 0.033(3) 0.039(3) 0.044(3) -0.001(2) 0.010(3) 0.006(2) C4 0.0228(11) 0.0310(13) 0.0223(11) 0.0008(10) 0.0073(9) -0.0005(10) C5 0.0172(10) 0.0301(13) 0.0254(11) 0.0023(10) 0.0101(9) 0.0018(9) C6 0.0168(11) 0.0373(14) 0.0254(11) 0.0032(10) 0.0050(9) 0.0007(10) C7 0.0204(11) 0.0372(14) 0.0223(11) -0.0028(10) 0.0054(9) -0.0059(10) C8 0.0195(10) 0.0296(13) 0.0242(11) -0.0020(10) 0.0091(9) -0.0028(9) C9 0.0216(11) 0.0305(13) 0.0235(11) -0.0020(10) 0.0050(9) -0.0054(9) C10 0.040(3) 0.050(3) 0.039(4) -0.002(3) 0.015(3) 0.002(2) C11 0.0209(15) 0.0319(18) 0.038(3) 0.0045(16) 0.007(2) 0.0051(12) C12 0.026(2) 0.028(2) 0.038(2) 0.002(2) -0.0019(16) 0.0033(19) S2 0.0423(6) 0.0308(5) 0.0272(5) 0.0007(3) 0.0135(4) -0.0040(4) S2X 0.043(3) 0.039(2) 0.041(3) -0.007(2) 0.016(2) 0.001(2) C13 0.0215(11) 0.0293(13) 0.0199(10) -0.0007(10) 0.0036(9) -0.0006(9) C14 0.0230(11) 0.0352(14) 0.0266(11) -0.0039(10) 0.0054(10) 0.0030(10) C15 0.0241(12) 0.0284(13) 0.0379(13) -0.0013(11) 0.0106(11) 0.0012(10) C16 0.0251(12) 0.0426(16) 0.0438(15) -0.0047(13) 0.0004(12) 0.0018(11) N2 0.0180(9) 0.0371(12) 0.0243(9) -0.0002(9) 0.0064(7) -0.0011(8) S3 0.0238(5) 0.0448(6) 0.0339(5) 0.0019(4) 0.0062(4) -0.0118(4) C17 0.035(3) 0.037(2) 0.038(2) 0.007(2) 0.006(2) -0.0048(18) C18 0.0278(19) 0.039(2) 0.037(3) 0.0079(19) 0.004(2) -0.0017(16) C19 0.028(3) 0.050(3) 0.040(3) 0.004(2) 0.009(3) -0.010(2) S3X 0.029(2) 0.037(2) 0.059(3) 0.0106(18) 0.010(2) 0.006(2) C20 0.0229(11) 0.0419(14) 0.0254(11) 0.0063(11) 0.0049(9) -0.0049(10) C21 0.0193(11) 0.0421(15) 0.0234(11) 0.0014(11) 0.0034(9) -0.0049(10) C22 0.0199(11) 0.0508(17) 0.0335(13) 0.0072(12) 0.0098(10) -0.0017(11) C23 0.0202(11) 0.0515(17) 0.0333(13) 0.0007(12) 0.0109(10) 0.0040(11) C24 0.0198(11) 0.0424(15) 0.0244(12) -0.0012(11) 0.0032(9) 0.0035(10) C25 0.0194(11) 0.0443(15) 0.0291(12) -0.0025(11) 0.0058(9) 0.0031(10) C26 0.031(3) 0.044(4) 0.041(3) -0.002(3) 0.012(2) 0.007(3) C27 0.0222(17) 0.039(2) 0.032(2) -0.0051(18) 0.0025(17) 0.0060(15) C28 0.0239(17) 0.031(2) 0.042(3) -0.0034(18) -0.0010(19) 0.0009(16) S4 0.0374(7) 0.0391(6) 0.0298(5) 0.0020(4) 0.0145(4) -0.0023(4) S4X 0.040(3) 0.049(3) 0.041(3) -0.012(2) 0.009(2) 0.013(2) C29 0.0220(11) 0.0356(14) 0.0242(11) -0.0010(10) 0.0093(9) -0.0012(10) C30 0.0214(11) 0.0398(15) 0.0305(12) -0.0039(11) 0.0084(10) -0.0027(10) C31 0.0265(13) 0.0343(14) 0.0319(13) 0.0026(11) 0.0055(11) -0.0020(10) C32 0.0278(13) 0.0478(17) 0.0484(15) 0.0028(13) 0.0164(12) -0.0003(12) _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 N1 C5 1.385(3) . ? N1 C8 1.383(3) . ? N1 C13 1.456(3) . ? S1 C1 1.724(4) . ? S1 C4 1.710(2) . ? C1 H1 0.950 . ? C1 C2 1.383(5) . ? C2 H2 0.950 . ? C2 C3 1.419(10) . ? C3 H3 0.950 . ? C3 C4 1.351(8) . ? S1X C1X 1.704(14) . ? S1X C4 1.637(9) . ? C1X H1X 0.950 . ? C1X C2X 1.369(14) . ? C2X H2X 0.950 . ? C2X C3X 1.423(15) . ? C3X H3X 0.950 . ? C3X C4 1.370(13) . ? C4 C5 1.460(3) . ? C5 C6 1.378(3) . ? C6 H6 0.950 . ? C6 C7 1.402(4) . ? C7 H7 0.950 . ? C7 C8 1.381(3) . ? C8 C9 1.463(3) . ? C9 C10 1.327(9) . ? C9 S2 1.719(2) . ? C9 C10X 1.361(13) . ? C9 S2X 1.594(8) . ? C10 H10 0.950 . ? C10 C11 1.441(10) . ? C11 H11 0.950 . ? C11 C12 1.390(5) . ? C12 H12 0.950 . ? C12 S2 1.713(4) . ? C10X H10X 0.950 . ? C10X C11X 1.432(15) . ? C11X H11X 0.950 . ? C11X C12X 1.385(14) . ? C12X H12X 0.950 . ? C12X S2X 1.713(14) . ? C13 H13A 0.990 . ? C13 H13B 0.990 . ? C13 C14 1.534(3) . ? C14 H14A 0.990 . ? C14 H14B 0.990 . ? C14 C15 1.470(3) . ? C15 C16 1.181(3) . ? C16 H16 0.950 . ? N2 C21 1.387(3) . ? N2 C24 1.386(3) . ? N2 C29 1.459(3) . ? S3 C17 1.718(5) . ? S3 C20 1.717(2) . ? C17 H17 0.950 . ? C17 C18 1.372(6) . ? C18 H18 0.950 . ? C18 C19 1.411(10) . ? C19 H19 0.950 . ? C19 C20 1.370(8) . ? S3X C17X 1.706(14) . ? S3X C20 1.623(7) . ? C17X H17X 0.950 . ? C17X C18X 1.389(14) . ? C18X H18X 0.950 . ? C18X C19X 1.425(15) . ? C19X H19X 0.950 . ? C19X C20 1.350(12) . ? C20 C21 1.457(4) . ? C21 C22 1.385(3) . ? C22 H22 0.950 . ? C22 C23 1.393(4) . ? C23 H23 0.950 . ? C23 C24 1.389(3) . ? C24 C25 1.461(4) . ? C25 C26 1.319(8) . ? C25 S4 1.709(3) . ? C25 C26X 1.371(13) . ? C25 S4X 1.622(8) . ? C26 H26 0.950 . ? C26 C27 1.435(11) . ? C27 H27 0.950 . ? C27 C28 1.390(6) . ? C28 H28 0.950 . ? C28 S4 1.714(4) . ? C26X H26X 0.950 . ? C26X C27X 1.442(15) . ? C27X H27X 0.950 . ? C27X C28X 1.366(13) . ? C28X H28X 0.950 . ? C28X S4X 1.714(13) . ? C29 H29A 0.990 . ? C29 H29B 0.990 . ? C29 C30 1.534(3) . ? C30 H30A 0.990 . ? C30 H30B 0.990 . ? C30 C31 1.470(3) . ? C31 C32 1.179(4) . ? C32 H32 0.950 . ? 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 C5 N1 C8 109.17(17) . . ? C5 N1 C13 125.70(18) . . ? C8 N1 C13 124.88(18) . . ? C1 S1 C4 92.57(16) . . ? S1 C1 H1 124.2 . . ? S1 C1 C2 111.6(3) . . ? H1 C1 C2 124.2 . . ? C1 C2 H2 125.1 . . ? C1 C2 C3 109.9(4) . . ? H2 C2 C3 125.1 . . ? C2 C3 H3 122.0 . . ? C2 C3 C4 116.0(7) . . ? H3 C3 C4 122.0 . . ? C1X S1X C4 94.3(8) . . ? S1X C1X H1X 124.5 . . ? S1X C1X C2X 110.9(13) . . ? H1X C1X C2X 124.6 . . ? C1X C2X H2X 125.0 . . ? C1X C2X C3X 110.1(14) . . ? H2X C2X C3X 125.0 . . ? C2X C3X H3X 123.0 . . ? C2X C3X C4 113.9(13) . . ? H3X C3X C4 123.0 . . ? S1 C4 C3 109.9(5) . . ? S1 C4 C5 122.88(16) . . ? C3 C4 C5 126.3(5) . . ? S1X C4 C3X 110.8(8) . . ? S1X C4 C5 123.9(4) . . ? C3X C4 C5 124.9(8) . . ? N1 C5 C4 125.24(19) . . ? N1 C5 C6 107.4(2) . . ? C4 C5 C6 127.3(2) . . ? C5 C6 H6 126.0 . . ? C5 C6 C7 108.0(2) . . ? H6 C6 C7 126.0 . . ? C6 C7 H7 126.0 . . ? C6 C7 C8 108.1(2) . . ? H7 C7 C8 126.0 . . ? N1 C8 C7 107.3(2) . . ? N1 C8 C9 123.92(18) . . ? C7 C8 C9 128.8(2) . . ? C8 C9 C10 128.1(5) . . ? C8 C9 S2 122.07(17) . . ? C8 C9 C10X 126.0(8) . . ? C8 C9 S2X 121.7(4) . . ? C10 C9 S2 109.8(5) . . ? C10X C9 S2X 112.3(8) . . ? C9 C10 H10 121.4 . . ? C9 C10 C11 117.2(7) . . ? H10 C10 C11 121.4 . . ? C10 C11 H11 126.2 . . ? C10 C11 C12 107.7(5) . . ? H11 C11 C12 126.2 . . ? C11 C12 H12 123.6 . . ? C11 C12 S2 112.8(4) . . ? H12 C12 S2 123.6 . . ? C9 S2 C12 92.33(19) . . ? C9 C10X H10X 123.4 . . ? C9 C10X C11X 113.3(13) . . ? H10X C10X C11X 123.4 . . ? C10X C11X H11X 125.8 . . ? C10X C11X C12X 108.4(14) . . ? H11X C11X C12X 125.8 . . ? C11X C12X H12X 124.9 . . ? C11X C12X S2X 110.3(13) . . ? H12X C12X S2X 124.9 . . ? C9 S2X C12X 94.3(8) . . ? N1 C13 H13A 109.4 . . ? N1 C13 H13B 109.4 . . ? N1 C13 C14 110.98(17) . . ? H13A C13 H13B 108.0 . . ? H13A C13 C14 109.4 . . ? H13B C13 C14 109.4 . . ? C13 C14 H14A 109.2 . . ? C13 C14 H14B 109.2 . . ? C13 C14 C15 112.15(18) . . ? H14A C14 H14B 107.9 . . ? H14A C14 C15 109.2 . . ? H14B C14 C15 109.2 . . ? C14 C15 C16 179.0(3) . . ? C15 C16 H16 180.0 . . ? C21 N2 C24 109.36(18) . . ? C21 N2 C29 124.8(2) . . ? C24 N2 C29 125.8(2) . . ? C17 S3 C20 93.20(18) . . ? S3 C17 H17 124.2 . . ? S3 C17 C18 111.6(4) . . ? H17 C17 C18 124.2 . . ? C17 C18 H18 124.7 . . ? C17 C18 C19 110.6(5) . . ? H18 C18 C19 124.7 . . ? C18 C19 H19 122.0 . . ? C18 C19 C20 116.0(7) . . ? H19 C19 C20 122.0 . . ? C17X S3X C20 93.2(7) . . ? S3X C17X H17X 124.5 . . ? S3X C17X C18X 111.0(12) . . ? H17X C17X C18X 124.5 . . ? C17X C18X H18X 125.5 . . ? C17X C18X C19X 109.1(13) . . ? H18X C18X C19X 125.5 . . ? C18X C19X H19X 123.4 . . ? C18X C19X C20 113.2(12) . . ? H19X C19X C20 123.4 . . ? S3 C20 C19 108.6(4) . . ? S3 C20 C21 119.22(16) . . ? C19 C20 C21 131.6(5) . . ? S3X C20 C19X 112.8(7) . . ? S3X C20 C21 125.0(3) . . ? C19X C20 C21 122.2(7) . . ? N2 C21 C20 125.0(2) . . ? N2 C21 C22 107.2(2) . . ? C20 C21 C22 127.8(2) . . ? C21 C22 H22 125.9 . . ? C21 C22 C23 108.3(2) . . ? H22 C22 C23 125.9 . . ? C22 C23 H23 125.9 . . ? C22 C23 C24 108.3(2) . . ? H23 C23 C24 125.9 . . ? N2 C24 C23 106.9(2) . . ? N2 C24 C25 126.4(2) . . ? C23 C24 C25 126.5(2) . . ? C24 C25 C26 123.2(5) . . ? C24 C25 S4 126.09(19) . . ? C24 C25 C26X 126.0(7) . . ? C24 C25 S4X 123.0(4) . . ? C26 C25 S4 110.7(5) . . ? C26X C25 S4X 110.2(8) . . ? C25 C26 H26 122.4 . . ? C25 C26 C27 115.2(8) . . ? H26 C26 C27 122.4 . . ? C26 C27 H27 124.7 . . ? C26 C27 C28 110.6(5) . . ? H27 C27 C28 124.7 . . ? C27 C28 H28 124.9 . . ? C27 C28 S4 110.2(3) . . ? H28 C28 S4 124.9 . . ? C25 S4 C28 93.28(17) . . ? C25 C26X H26X 122.9 . . ? C25 C26X C27X 114.2(12) . . ? H26X C26X C27X 122.9 . . ? C26X C27X H27X 125.1 . . ? C26X C27X C28X 109.8(13) . . ? H27X C27X C28X 125.1 . . ? C27X C28X H28X 124.9 . . ? C27X C28X S4X 110.2(12) . . ? H28X C28X S4X 124.9 . . ? C25 S4X C28X 95.4(8) . . ? N2 C29 H29A 109.5 . . ? N2 C29 H29B 109.5 . . ? N2 C29 C30 110.64(18) . . ? H29A C29 H29B 108.1 . . ? H29A C29 C30 109.5 . . ? H29B C29 C30 109.5 . . ? C29 C30 H30A 109.1 . . ? C29 C30 H30B 109.1 . . ? C29 C30 C31 112.29(19) . . ? H30A C30 H30B 107.9 . . ? H30A C30 C31 109.1 . . ? H30B C30 C31 109.1 . . ? C30 C31 C32 179.5(3) . . ? C31 C32 H32 180.0 . . ? 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 C4 S1 C1 C2 -1.3(4) . . . . ? S1 C1 C2 C3 1.3(9) . . . . ? C1 C2 C3 C4 -0.6(14) . . . . ? C4 S1X C1X C2X 1(2) . . . . ? S1X C1X C2X C3X -1(3) . . . . ? C1X C2X C3X C4 2(3) . . . . ? C2 C3 C4 S1 -0.3(14) . . . . ? C2 C3 C4 C5 -169.7(7) . . . . ? C2X C3X C4 S1X -1(3) . . . . ? C2X C3X C4 C5 171.3(16) . . . . ? C1X S1X C4 C3X 0.1(18) . . . . ? C1X S1X C4 C5 -172.3(10) . . . . ? C1 S1 C4 C3 0.9(8) . . . . ? C1 S1 C4 C5 170.7(3) . . . . ? C8 N1 C5 C4 -177.28(19) . . . . ? C8 N1 C5 C6 0.6(2) . . . . ? C13 N1 C5 C4 -2.8(3) . . . . ? C13 N1 C5 C6 175.05(18) . . . . ? S1 C4 C5 N1 51.9(3) . . . . ? S1 C4 C5 C6 -125.6(2) . . . . ? C3 C4 C5 N1 -140.0(9) . . . . ? C3 C4 C5 C6 42.6(9) . . . . ? S1X C4 C5 N1 -136.7(8) . . . . ? S1X C4 C5 C6 45.9(9) . . . . ? C3X C4 C5 N1 52.0(14) . . . . ? C3X C4 C5 C6 -125.4(14) . . . . ? N1 C5 C6 C7 -0.6(2) . . . . ? C4 C5 C6 C7 177.2(2) . . . . ? C5 C6 C7 C8 0.4(2) . . . . ? C6 C7 C8 N1 0.0(2) . . . . ? C6 C7 C8 C9 179.5(2) . . . . ? C5 N1 C8 C7 -0.4(2) . . . . ? C5 N1 C8 C9 -179.89(19) . . . . ? C13 N1 C8 C7 -174.88(18) . . . . ? C13 N1 C8 C9 5.6(3) . . . . ? N1 C8 C9 C10 -115.8(8) . . . . ? N1 C8 C9 S2 68.0(3) . . . . ? N1 C8 C9 C10X 60.0(12) . . . . ? N1 C8 C9 S2X -118.2(6) . . . . ? C7 C8 C9 C10 64.8(8) . . . . ? C7 C8 C9 S2 -111.4(2) . . . . ? C7 C8 C9 C10X -119.4(12) . . . . ? C7 C8 C9 S2X 62.4(7) . . . . ? C8 C9 C10 C11 -173.2(6) . . . . ? S2 C9 C10 C11 3.4(12) . . . . ? C9 C10 C11 C12 -4.8(13) . . . . ? C10 C11 C12 S2 4.0(10) . . . . ? C8 C9 S2 C12 176.1(3) . . . . ? C10 C9 S2 C12 -0.7(7) . . . . ? C11 C12 S2 C9 -2.1(6) . . . . ? C8 C9 C10X C11X 171.7(17) . . . . ? S2X C9 C10X C11X -10(2) . . . . ? C9 C10X C11X C12X 13(4) . . . . ? C10X C11X C12X S2X -11(4) . . . . ? C8 C9 S2X C12X -178.7(13) . . . . ? C10X C9 S2X C12X 2.9(18) . . . . ? C11X C12X S2X C9 5(3) . . . . ? C5 N1 C13 C14 -97.1(2) . . . . ? C8 N1 C13 C14 76.5(3) . . . . ? N1 C13 C14 C15 172.54(19) . . . . ? C13 C14 C15 C16 -54(16) . . . . ? C20 S3 C17 C18 -1.1(6) . . . . ? S3 C17 C18 C19 -0.1(10) . . . . ? C17 C18 C19 C20 1.7(14) . . . . ? S3X C17X C18X C19X -5(3) . . . . ? C17X C18X C19X C20 9(3) . . . . ? C18X C19X C20 S3X -9(2) . . . . ? C18X C19X C20 C21 172.8(14) . . . . ? C18 C19 C20 S3 -2.4(12) . . . . ? C18 C19 C20 C21 -173.0(6) . . . . ? C17X S3X C20 C19X 5.7(16) . . . . ? C17X S3X C20 C21 -176.6(11) . . . . ? C17 S3 C20 C19 2.0(7) . . . . ? C17 S3 C20 C21 173.9(3) . . . . ? C24 N2 C21 C20 177.8(2) . . . . ? C24 N2 C21 C22 -0.5(2) . . . . ? C29 N2 C21 C20 1.4(3) . . . . ? C29 N2 C21 C22 -176.97(19) . . . . ? S3 C20 C21 N2 152.47(17) . . . . ? S3 C20 C21 C22 -29.6(3) . . . . ? C19 C20 C21 N2 -37.8(9) . . . . ? C19 C20 C21 C22 140.2(8) . . . . ? S3X C20 C21 N2 -32.5(6) . . . . ? S3X C20 C21 C22 145.5(6) . . . . ? C19X C20 C21 N2 144.9(10) . . . . ? C19X C20 C21 C22 -37.1(11) . . . . ? N2 C21 C22 C23 0.3(3) . . . . ? C20 C21 C22 C23 -177.9(2) . . . . ? C21 C22 C23 C24 0.0(3) . . . . ? C21 N2 C24 C23 0.6(2) . . . . ? C21 N2 C24 C25 -175.8(2) . . . . ? C29 N2 C24 C23 176.95(19) . . . . ? C29 N2 C24 C25 0.6(3) . . . . ? C22 C23 C24 N2 -0.4(3) . . . . ? C22 C23 C24 C25 176.0(2) . . . . ? N2 C24 C25 C26 147.4(8) . . . . ? N2 C24 C25 S4 -34.2(3) . . . . ? N2 C24 C25 C26X -41.8(12) . . . . ? N2 C24 C25 S4X 149.5(7) . . . . ? C23 C24 C25 C26 -28.2(9) . . . . ? C23 C24 C25 S4 150.2(2) . . . . ? C23 C24 C25 C26X 142.6(12) . . . . ? C23 C24 C25 S4X -26.2(8) . . . . ? C24 C25 C26 C27 176.2(6) . . . . ? S4 C25 C26 C27 -2.4(13) . . . . ? C25 C26 C27 C28 2.2(14) . . . . ? C26 C27 C28 S4 -0.8(8) . . . . ? C24 C25 S4 C28 -176.9(2) . . . . ? C26 C25 S4 C28 1.6(8) . . . . ? C27 C28 S4 C25 -0.4(3) . . . . ? C24 C25 C26X C27X -176.4(12) . . . . ? S4X C25 C26X C27X -6(2) . . . . ? C25 C26X C27X C28X 5(3) . . . . ? C26X C27X C28X S4X -1(3) . . . . ? C24 C25 S4X C28X 175.3(8) . . . . ? C26X C25 S4X C28X 4.9(16) . . . . ? C27X C28X S4X C25 -2.2(19) . . . . ? C21 N2 C29 C30 97.9(2) . . . . ? C24 N2 C29 C30 -78.0(3) . . . . ? N2 C29 C30 C31 -173.2(2) . . . . ? C29 C30 C31 C32 -60(46) . . . . ? _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 62.30 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 0.270 _refine_diff_density_min -0.217 _refine_diff_density_rms 0.050 #===END data_ah192_compound_7 _database_code_depnum_ccdc_archive 'CCDC 785463' #TrackingRef 'OBC-Revised-CIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H15 N S2' _chemical_formula_sum 'C17 H15 N S2' _chemical_formula_weight 297.42 _chemical_absolute_configuration . 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 orthorhombic _symmetry_space_group_name_H-M 'P c a 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y, z' '-x+1/2, y, z+1/2' _cell_length_a 18.2767(8) _cell_length_b 5.6221(2) _cell_length_c 14.5289(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1492.89(10) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2725 _cell_measurement_theta_min 3.01 _cell_measurement_theta_max 29.44 _exptl_crystal_description lath _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.323 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 624 _exptl_absorpt_coefficient_mu 0.345 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.935 _exptl_absorpt_correction_T_max 0.995 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube with Enhance optics' _diffrn_radiation_monochromator none _diffrn_measurement_device_type 'Oxford Diffraction Gemini A Ultra diffractometer' _diffrn_measurement_method 'thick-slice \w scans' _diffrn_detector_area_resol_mean 10.3968 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6767 _diffrn_reflns_av_R_equivalents 0.0511 _diffrn_reflns_av_sigmaI/netI 0.0721 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.58 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2324 _reflns_number_gt 1805 _reflns_threshold_expression I>2\s(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL and local programs' _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^)+(0.0292P)^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 SHELXL _refine_ls_extinction_coef 0.0018(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.02(9) _refine_ls_number_reflns 2324 _refine_ls_number_parameters 205 _refine_ls_number_restraints 122 _refine_ls_R_factor_all 0.0504 _refine_ls_R_factor_gt 0.0356 _refine_ls_wR_factor_ref 0.0655 _refine_ls_wR_factor_gt 0.0633 _refine_ls_goodness_of_fit_ref 0.914 _refine_ls_restrained_S_all 0.912 _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 N1 N 0.54379(12) 0.6232(4) 0.42167(16) 0.0156(6) Uani 1 1 d . A . S1 S 0.63454(10) 0.0704(3) 0.54510(14) 0.0224(4) Uani 0.757(4) 1 d PDU A 1 C1 C 0.7210(3) -0.0003(9) 0.5089(3) 0.0202(11) Uani 0.757(4) 1 d PDU A 1 H1 H 0.7460 -0.1416 0.5262 0.024 Uiso 0.757(4) 1 calc PR A 1 C2 C 0.7501(3) 0.1695(8) 0.4523(3) 0.0175(11) Uani 0.757(4) 1 d PDU A 1 H2 H 0.7972 0.1623 0.4250 0.021 Uiso 0.757(4) 1 calc PR A 1 C3 C 0.6989(6) 0.359(3) 0.4403(13) 0.019(2) Uani 0.757(4) 1 d PDU A 1 H3 H 0.7088 0.4936 0.4025 0.023 Uiso 0.757(4) 1 calc PR A 1 S1X S 0.7129(6) 0.368(2) 0.4365(12) 0.0269(18) Uani 0.243(4) 1 d PDU A 2 C1X C 0.7457(9) 0.102(3) 0.4739(12) 0.015(3) Uiso 0.243(4) 1 d PDU A 2 H1X H 0.7929 0.0424 0.4586 0.018 Uiso 0.243(4) 1 calc PR A 2 C2X C 0.6974(8) -0.018(3) 0.5280(12) 0.014(3) Uiso 0.243(4) 1 d PDU A 2 H2X H 0.7062 -0.1664 0.5570 0.017 Uiso 0.243(4) 1 calc PR A 2 C3X C 0.6314(12) 0.117(3) 0.534(2) 0.020(4) Uiso 0.243(4) 1 d PDU A 2 H3X H 0.5895 0.0651 0.5672 0.025 Uiso 0.243(4) 1 calc PR A 2 C4 C 0.63461(17) 0.3328(5) 0.48763(19) 0.0180(7) Uani 1 1 d DU . . C5 C 0.57219(16) 0.4956(5) 0.4953(2) 0.0172(7) Uani 1 1 d . A . C6 C 0.53107(16) 0.5457(5) 0.5712(2) 0.0208(7) Uani 1 1 d . . . H6 H 0.5380 0.4818 0.6311 0.025 Uiso 1 1 calc R A . C7 C 0.47662(16) 0.7086(4) 0.5452(2) 0.0198(7) Uani 1 1 d . A . H7 H 0.4402 0.7740 0.5844 0.024 Uiso 1 1 calc R . . C8 C 0.48531(16) 0.7567(5) 0.4531(2) 0.0170(7) Uani 1 1 d . . . C9 C 0.44518(14) 0.9328(5) 0.39871(19) 0.0181(7) Uani 1 1 d D A . C10 C 0.42201(14) 1.1543(5) 0.4314(2) 0.0165(7) Uani 1 1 d D . . H10 H 0.4332 1.2154 0.4908 0.020 Uiso 1 1 calc R A . C11 C 0.37920(17) 1.2771(5) 0.3637(2) 0.0271(8) Uani 1 1 d D A . H11 H 0.3585 1.4298 0.3740 0.032 Uiso 1 1 calc R . . C12 C 0.37111(17) 1.1577(6) 0.2850(3) 0.0304(8) Uani 1 1 d D . . H12 H 0.3445 1.2160 0.2336 0.037 Uiso 1 1 calc R A . S2 S 0.41409(5) 0.88824(15) 0.28730(7) 0.0355(3) Uani 1 1 d D A . C13 C 0.56965(16) 0.6131(5) 0.32707(19) 0.0164(7) Uani 1 1 d . . . H13A H 0.5271 0.5944 0.2855 0.020 Uiso 1 1 calc R A . H13B H 0.6013 0.4716 0.3195 0.020 Uiso 1 1 calc R . . C14 C 0.61256(16) 0.8349(5) 0.2990(2) 0.0217(7) Uani 1 1 d . A . H14A H 0.6560 0.8523 0.3391 0.026 Uiso 1 1 calc R . . H14B H 0.5815 0.9775 0.3070 0.026 Uiso 1 1 calc R . . C15 C 0.6372(2) 0.8164(5) 0.1977(2) 0.0290(8) Uani 1 1 d . . . H15A H 0.5935 0.7936 0.1583 0.035 Uiso 1 1 calc R A . H15B H 0.6607 0.9677 0.1793 0.035 Uiso 1 1 calc R . . C16 C 0.6884(2) 0.6203(6) 0.1818(2) 0.0283(8) Uani 1 1 d . A . C17 C 0.7296(2) 0.4661(7) 0.1694(3) 0.0429(10) Uani 1 1 d . . . H17 H 0.7632 0.3400 0.1593 0.051 Uiso 1 1 calc R A . 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 N1 0.0150(13) 0.0180(12) 0.0137(14) -0.0021(11) -0.0011(11) 0.0017(11) S1 0.0282(8) 0.0178(8) 0.0211(8) 0.0040(6) -0.0022(6) -0.0029(6) C1 0.017(3) 0.021(2) 0.023(3) -0.001(2) -0.005(2) 0.007(2) C2 0.017(2) 0.014(2) 0.021(3) 0.003(2) -0.0010(19) -0.0010(19) C3 0.017(4) 0.017(3) 0.024(4) 0.004(3) -0.004(4) -0.002(3) S1X 0.014(3) 0.033(3) 0.034(3) 0.004(3) 0.007(3) -0.001(3) C4 0.0194(15) 0.0156(14) 0.0189(16) -0.0012(13) -0.0061(14) 0.0002(13) C5 0.0207(17) 0.0118(14) 0.0190(17) 0.0054(14) -0.0042(16) -0.0034(13) C6 0.0266(19) 0.0230(15) 0.0129(17) 0.0012(14) 0.0005(15) -0.0016(15) C7 0.0147(16) 0.0248(14) 0.0198(18) -0.0017(17) 0.0049(16) 0.0023(13) C8 0.0149(16) 0.0184(15) 0.0176(17) -0.0021(15) 0.0001(14) 0.0012(14) C9 0.0149(17) 0.0231(17) 0.0164(16) -0.0015(14) 0.0003(14) -0.0034(14) C10 0.0102(15) 0.0153(14) 0.0241(17) 0.0013(14) -0.0010(14) -0.0042(13) C11 0.0193(19) 0.0186(17) 0.043(2) -0.0001(18) 0.0070(17) -0.0017(15) C12 0.0254(18) 0.0339(18) 0.032(2) 0.0140(19) 0.001(2) 0.0079(15) S2 0.0449(6) 0.0347(4) 0.0271(5) -0.0025(5) -0.0085(5) 0.0148(4) C13 0.0202(17) 0.0161(14) 0.0130(16) -0.0025(14) 0.0009(13) 0.0000(13) C14 0.0228(17) 0.0211(16) 0.0212(18) 0.0013(16) 0.0016(15) 0.0022(13) C15 0.035(2) 0.0305(19) 0.0215(18) 0.0068(15) 0.0037(18) -0.0002(17) C16 0.034(2) 0.031(2) 0.020(2) -0.0030(17) 0.0101(16) -0.0126(19) C17 0.048(3) 0.0327(19) 0.048(2) -0.007(2) 0.018(2) -0.004(2) _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 N1 C5 1.388(4) . ? N1 C8 1.384(4) . ? N1 C13 1.455(4) . ? S1 C1 1.713(5) . ? S1 C4 1.695(3) . ? C1 H1 0.950 . ? C1 C2 1.367(6) . ? C2 H2 0.950 . ? C2 C3 1.430(12) . ? C3 H3 0.950 . ? C3 C4 1.370(10) . ? S1X C1X 1.701(14) . ? S1X C4 1.624(9) . ? C1X H1X 0.950 . ? C1X C2X 1.358(14) . ? C2X H2X 0.950 . ? C2X C3X 1.428(16) . ? C3X H3X 0.950 . ? C3X C4 1.389(15) . ? C4 C5 1.467(4) . ? C5 C6 1.364(4) . ? C6 H6 0.950 . ? C6 C7 1.404(4) . ? C7 H7 0.950 . ? C7 C8 1.375(4) . ? C8 C9 1.464(4) . ? C9 C10 1.398(4) . ? C9 S2 1.734(3) . ? C10 H10 0.950 . ? C10 C11 1.434(4) . ? C11 H11 0.950 . ? C11 C12 1.334(5) . ? C12 H12 0.950 . ? C12 S2 1.707(3) . ? C13 H13A 0.990 . ? C13 H13B 0.990 . ? C13 C14 1.528(4) . ? C14 H14A 0.990 . ? C14 H14B 0.990 . ? C14 C15 1.542(4) . ? C15 H15A 0.990 . ? C15 H15B 0.990 . ? C15 C16 1.465(5) . ? C16 C17 1.162(5) . ? C17 H17 0.950 . ? 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 C5 N1 C8 108.4(2) . . ? C5 N1 C13 125.9(2) . . ? C8 N1 C13 125.7(2) . . ? C1 S1 C4 92.9(2) . . ? S1 C1 H1 123.8 . . ? S1 C1 C2 112.4(3) . . ? H1 C1 C2 123.8 . . ? C1 C2 H2 125.0 . . ? C1 C2 C3 110.0(6) . . ? H2 C2 C3 125.0 . . ? C2 C3 H3 122.7 . . ? C2 C3 C4 114.7(9) . . ? H3 C3 C4 122.7 . . ? C1X S1X C4 93.3(7) . . ? S1X C1X H1X 123.5 . . ? S1X C1X C2X 112.9(12) . . ? H1X C1X C2X 123.5 . . ? C1X C2X H2X 125.6 . . ? C1X C2X C3X 108.9(13) . . ? H2X C2X C3X 125.6 . . ? C2X C3X H3X 123.3 . . ? C2X C3X C4 113.4(14) . . ? H3X C3X C4 123.3 . . ? S1 C4 C3 110.1(5) . . ? S1 C4 C5 120.3(2) . . ? C3 C4 C5 129.6(6) . . ? S1X C4 C3X 111.4(8) . . ? S1X C4 C5 130.1(5) . . ? C3X C4 C5 118.3(9) . . ? N1 C5 C4 123.7(3) . . ? N1 C5 C6 108.1(2) . . ? C4 C5 C6 128.2(3) . . ? C5 C6 H6 126.0 . . ? C5 C6 C7 107.9(3) . . ? H6 C6 C7 126.0 . . ? C6 C7 H7 126.0 . . ? C6 C7 C8 108.0(3) . . ? H7 C7 C8 126.0 . . ? N1 C8 C7 107.7(3) . . ? N1 C8 C9 125.2(3) . . ? C7 C8 C9 126.9(3) . . ? C8 C9 C10 124.8(3) . . ? C8 C9 S2 124.8(2) . . ? C10 C9 S2 110.3(2) . . ? C9 C10 H10 124.4 . . ? C9 C10 C11 111.1(3) . . ? H10 C10 C11 124.4 . . ? C10 C11 H11 123.0 . . ? C10 C11 C12 114.0(3) . . ? H11 C11 C12 123.0 . . ? C11 C12 H12 123.9 . . ? C11 C12 S2 112.3(3) . . ? H12 C12 S2 123.9 . . ? C9 S2 C12 92.34(18) . . ? N1 C13 H13A 109.0 . . ? N1 C13 H13B 109.0 . . ? N1 C13 C14 112.8(2) . . ? H13A C13 H13B 107.8 . . ? H13A C13 C14 109.0 . . ? H13B C13 C14 109.0 . . ? C13 C14 H14A 109.6 . . ? C13 C14 H14B 109.6 . . ? C13 C14 C15 110.5(2) . . ? H14A C14 H14B 108.1 . . ? H14A C14 C15 109.6 . . ? H14B C14 C15 109.6 . . ? C14 C15 H15A 109.0 . . ? C14 C15 H15B 109.0 . . ? C14 C15 C16 112.8(3) . . ? H15A C15 H15B 107.8 . . ? H15A C15 C16 109.0 . . ? H15B C15 C16 109.0 . . ? C15 C16 C17 179.4(4) . . ? C16 C17 H17 180.0 . . ? 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 C4 S1 C1 C2 -1.1(4) . . . . ? S1 C1 C2 C3 0.3(10) . . . . ? C1 C2 C3 C4 0.9(17) . . . . ? C4 S1X C1X C2X -1.1(19) . . . . ? S1X C1X C2X C3X 2(3) . . . . ? C1X C2X C3X C4 -2(3) . . . . ? C2 C3 C4 S1 -1.7(16) . . . . ? C2 C3 C4 C5 176.5(7) . . . . ? C2X C3X C4 S1X 1(3) . . . . ? C2X C3X C4 C5 -175.2(16) . . . . ? C1X S1X C4 C3X -0.2(19) . . . . ? C1X S1X C4 C5 175.9(7) . . . . ? C1 S1 C4 C3 1.6(9) . . . . ? C1 S1 C4 C5 -176.8(3) . . . . ? C8 N1 C5 C4 179.6(2) . . . . ? C8 N1 C5 C6 1.1(3) . . . . ? C13 N1 C5 C4 1.3(4) . . . . ? C13 N1 C5 C6 -177.3(2) . . . . ? S1 C4 C5 N1 -139.8(3) . . . . ? S1 C4 C5 C6 38.4(4) . . . . ? C3 C4 C5 N1 42.1(12) . . . . ? C3 C4 C5 C6 -139.7(11) . . . . ? S1X C4 C5 N1 45.8(10) . . . . ? S1X C4 C5 C6 -135.9(9) . . . . ? C3X C4 C5 N1 -138.4(16) . . . . ? C3X C4 C5 C6 39.8(16) . . . . ? N1 C5 C6 C7 -0.6(3) . . . . ? C4 C5 C6 C7 -179.0(3) . . . . ? C5 C6 C7 C8 -0.1(3) . . . . ? C6 C7 C8 N1 0.8(3) . . . . ? C6 C7 C8 C9 -173.9(3) . . . . ? C5 N1 C8 C7 -1.1(3) . . . . ? C5 N1 C8 C9 173.7(3) . . . . ? C13 N1 C8 C7 177.2(2) . . . . ? C13 N1 C8 C9 -8.0(4) . . . . ? N1 C8 C9 C10 -138.2(3) . . . . ? N1 C8 C9 S2 46.6(4) . . . . ? C7 C8 C9 C10 35.6(5) . . . . ? C7 C8 C9 S2 -139.6(3) . . . . ? C8 C9 C10 C11 -175.4(3) . . . . ? S2 C9 C10 C11 0.4(3) . . . . ? C9 C10 C11 C12 -0.5(4) . . . . ? C10 C11 C12 S2 0.3(4) . . . . ? C11 C12 S2 C9 -0.1(3) . . . . ? C8 C9 S2 C12 175.6(3) . . . . ? C10 C9 S2 C12 -0.2(2) . . . . ? C5 N1 C13 C14 -106.2(3) . . . . ? C8 N1 C13 C14 75.7(3) . . . . ? N1 C13 C14 C15 -178.8(2) . . . . ? C13 C14 C15 C16 -64.0(3) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.235 _refine_diff_density_min -0.256 _refine_diff_density_rms 0.046 #===END data_ah145_compound_9b _database_code_depnum_ccdc_archive 'CCDC 785464' #TrackingRef 'OBC-Revised-CIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H23 N3 O5 S' _chemical_formula_sum 'C22 H23 N3 O5 S' _chemical_formula_weight 441.49 _chemical_absolute_configuration ad loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 8.0959(4) _cell_length_b 5.7246(3) _cell_length_c 22.4170(9) _cell_angle_alpha 90.00 _cell_angle_beta 95.369(4) _cell_angle_gamma 90.00 _cell_volume 1034.38(9) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2981 _cell_measurement_theta_min 1.98 _cell_measurement_theta_max 66.55 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.05 _exptl_crystal_size_mid 0.001 _exptl_crystal_size_min 0.001 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.418 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 464 _exptl_absorpt_coefficient_mu 1.741 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.918 _exptl_absorpt_correction_T_max 0.998 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'sealed tube with Enhance Ultra optics' _diffrn_radiation_monochromator none _diffrn_measurement_device_type 'Oxford Diffraction Gemini A Ultra diffractometer' _diffrn_measurement_method 'thick-slice \w scans' _diffrn_detector_area_resol_mean 10.3968 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10720 _diffrn_reflns_av_R_equivalents 0.1127 _diffrn_reflns_av_sigmaI/netI 0.0974 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.98 _diffrn_reflns_theta_max 67.16 _reflns_number_total 3529 _reflns_number_gt 2567 _reflns_threshold_expression I>2\s(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL and local programs' _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^)+(0.0779P)^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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0017(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.07(4) _refine_ls_number_reflns 3529 _refine_ls_number_parameters 310 _refine_ls_number_restraints 110 _refine_ls_R_factor_all 0.0903 _refine_ls_R_factor_gt 0.0578 _refine_ls_wR_factor_ref 0.1445 _refine_ls_wR_factor_gt 0.1278 _refine_ls_goodness_of_fit_ref 0.978 _refine_ls_restrained_S_all 0.964 _refine_ls_shift/su_max 0.005 _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 O1' O 0.1991(4) 0.1971(6) 0.85956(13) 0.0298(8) Uani 1 1 d . . . C1' C 0.3245(6) 0.3294(8) 0.89195(19) 0.0301(10) Uani 1 1 d . . . H1' H 0.4296 0.2365 0.8967 0.036 Uiso 1 1 calc R . . C2' C 0.2654(6) 0.3749(8) 0.95324(19) 0.0318(11) Uani 1 1 d . . . H2'A H 0.2012 0.5219 0.9537 0.038 Uiso 1 1 calc R . . H2'B H 0.3595 0.3815 0.9848 0.038 Uiso 1 1 calc R . . C3' C 0.1560(6) 0.1628(9) 0.9611(2) 0.0360(12) Uani 1 1 d . . . H3'A H 0.0711 0.1942 0.9897 0.043 Uiso 1 1 calc R . . O3' O 0.2537(5) -0.0400(6) 0.97774(15) 0.0448(9) Uani 1 1 d D . . H3' H 0.307(6) -0.005(11) 1.0107(15) 0.054 Uiso 1 1 d D . . C4' C 0.0768(6) 0.1169(8) 0.89804(17) 0.0292(10) Uani 1 1 d . . . H4' H 0.0640 -0.0558 0.8927 0.035 Uiso 1 1 calc R . . C5' C -0.0885(7) 0.2292(9) 0.8805(2) 0.0415(13) Uani 1 1 d . . . H5'A H -0.1276 0.1853 0.8389 0.050 Uiso 1 1 calc R . . H5'B H -0.1709 0.1724 0.9071 0.050 Uiso 1 1 calc R . . O5' O -0.0749(5) 0.4783(7) 0.88508(16) 0.0489(10) Uani 1 1 d D . . H5' H -0.171(4) 0.537(10) 0.888(2) 0.059 Uiso 1 1 d D . . N1 N 0.3510(4) 0.5459(7) 0.85628(15) 0.0260(8) Uani 1 1 d . . . C2 C 0.5036(6) 0.6608(9) 0.87019(19) 0.0306(11) Uani 1 1 d . . . O2 O 0.6024(4) 0.5813(6) 0.90990(13) 0.0369(8) Uani 1 1 d . . . N3 N 0.5377(5) 0.8555(7) 0.83789(16) 0.0315(9) Uani 1 1 d . . . C4 C 0.4223(6) 0.9107(8) 0.79537(19) 0.0288(10) Uani 1 1 d . . . O4 O 0.4430(4) 1.1014(5) 0.75996(13) 0.0310(7) Uani 1 1 d . . . C5 C 0.2724(6) 0.8000(8) 0.77821(18) 0.0256(10) Uani 1 1 d . . . C6 C 0.2373(6) 0.6117(8) 0.81201(18) 0.0282(10) Uani 1 1 d . . . H6 H 0.1356 0.5295 0.8045 0.034 Uiso 1 1 calc R . . C7 C 0.1975(6) 0.9329(8) 0.72746(19) 0.0296(11) Uani 1 1 d . . . H7 H 0.0942 0.9017 0.7052 0.036 Uiso 1 1 calc R . . C8 C 0.3005(6) 1.1054(8) 0.71812(18) 0.0286(10) Uani 1 1 d . . . C9 C 0.3043(6) 1.2929(9) 0.6729(2) 0.0328(11) Uani 1 1 d . . . H9A H 0.2980 1.4460 0.6931 0.039 Uiso 1 1 calc R . . H9B H 0.2053 1.2781 0.6437 0.039 Uiso 1 1 calc R . . C10 C 0.4605(6) 1.2872(8) 0.6391(2) 0.0296(10) Uani 1 1 d . . . H10A H 0.4604 1.4232 0.6118 0.036 Uiso 1 1 calc R . . H10B H 0.5604 1.2976 0.6680 0.036 Uiso 1 1 calc R . . C11 C 0.4659(5) 1.0616(8) 0.60302(18) 0.0286(11) Uani 1 1 d . . . H11A H 0.4664 0.9268 0.6307 0.034 Uiso 1 1 calc R . . H11B H 0.3643 1.0510 0.5749 0.034 Uiso 1 1 calc R . . N12 N 0.6114(4) 1.0475(7) 0.56908(14) 0.0275(9) Uani 1 1 d . . . C13 C 0.6198(7) 1.1578(9) 0.51536(19) 0.0353(12) Uani 1 1 d . . . H13 H 0.5405 1.2649 0.4974 0.042 Uiso 1 1 calc R . . C14 C 0.7616(6) 1.0879(9) 0.4920(2) 0.0361(11) Uani 1 1 d . . . H14 H 0.7972 1.1345 0.4546 0.043 Uiso 1 1 calc R . . C15 C 0.8454(6) 0.9339(9) 0.5334(2) 0.0356(12) Uani 1 1 d . . . H15 H 0.9486 0.8593 0.5294 0.043 Uiso 1 1 calc R . . C16 C 0.7491(6) 0.9110(8) 0.58134(19) 0.0280(10) Uani 1 1 d . A . C17 C 0.7826(6) 0.7661(8) 0.6347(2) 0.0305(10) Uani 1 1 d DU . . S18 S 0.8847(3) 0.5063(3) 0.62877(9) 0.0344(5) Uani 0.793(5) 1 d PDU A 1 C19 C 0.8849(10) 0.4539(13) 0.7051(3) 0.0301(15) Uani 0.793(5) 1 d PDU A 1 H19 H 0.9348 0.3210 0.7248 0.036 Uiso 0.793(5) 1 calc PR A 1 C20 C 0.8066(13) 0.6227(14) 0.7333(3) 0.0327(14) Uani 0.793(5) 1 d PDU A 1 H20 H 0.7906 0.6219 0.7747 0.039 Uiso 0.793(5) 1 calc PR A 1 C21 C 0.751(2) 0.803(3) 0.6923(5) 0.034(2) Uani 0.793(5) 1 d PDU A 1 H21 H 0.6956 0.9392 0.7045 0.040 Uiso 0.793(5) 1 calc PR A 1 S18X S 0.733(2) 0.827(3) 0.7046(5) 0.032(2) Uani 0.207(5) 1 d PDU A 2 C19X C 0.824(5) 0.568(5) 0.7316(12) 0.032(3) Uiso 0.207(5) 1 d PDU A 2 H19X H 0.8315 0.5227 0.7726 0.038 Uiso 0.207(5) 1 calc PR A 2 C20X C 0.881(5) 0.438(5) 0.6881(11) 0.033(3) Uiso 0.207(5) 1 d PDU A 2 H20X H 0.9285 0.2869 0.6936 0.039 Uiso 0.207(5) 1 calc PR A 2 C21X C 0.862(5) 0.561(5) 0.6323(13) 0.034(4) Uiso 0.207(5) 1 d PDU A 2 H21X H 0.9012 0.5025 0.5967 0.041 Uiso 0.207(5) 1 calc PR A 2 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 O1' 0.0318(18) 0.0311(19) 0.0274(16) -0.0036(13) 0.0072(14) -0.0006(15) C1' 0.033(3) 0.027(3) 0.030(2) -0.0015(19) 0.0026(19) -0.001(2) C2' 0.040(3) 0.026(3) 0.029(2) -0.0037(19) 0.006(2) 0.001(2) C3' 0.037(3) 0.041(3) 0.030(2) 0.000(2) 0.001(2) -0.002(2) O3' 0.062(2) 0.035(2) 0.0367(19) -0.0014(15) -0.0040(17) -0.0007(18) C4' 0.039(3) 0.027(3) 0.021(2) -0.0007(18) 0.0038(19) -0.007(2) C5' 0.034(3) 0.039(3) 0.051(3) -0.005(2) 0.007(2) -0.003(2) O5' 0.041(2) 0.053(3) 0.054(2) 0.0085(18) 0.0104(18) 0.0054(19) N1 0.0215(18) 0.032(2) 0.0250(18) -0.0039(15) 0.0017(14) 0.0046(16) C2 0.030(3) 0.036(3) 0.026(2) -0.009(2) 0.005(2) 0.003(2) O2 0.0272(18) 0.049(2) 0.0334(17) 0.0069(15) -0.0050(14) 0.0046(16) N3 0.026(2) 0.038(3) 0.0297(19) -0.0030(17) 0.0011(16) -0.0024(19) C4 0.028(2) 0.030(3) 0.030(2) -0.003(2) 0.0107(19) 0.004(2) O4 0.0296(17) 0.0313(19) 0.0325(16) -0.0018(14) 0.0054(13) 0.0003(15) C5 0.025(2) 0.028(3) 0.024(2) -0.0047(18) 0.0052(18) 0.003(2) C6 0.025(2) 0.032(3) 0.028(2) -0.0055(19) 0.0070(18) 0.004(2) C7 0.029(2) 0.033(3) 0.027(2) -0.0030(19) 0.0033(19) 0.008(2) C8 0.025(2) 0.033(3) 0.028(2) -0.003(2) 0.0048(18) 0.006(2) C9 0.036(3) 0.033(3) 0.031(2) -0.006(2) 0.011(2) 0.006(2) C10 0.031(3) 0.030(3) 0.029(2) 0.0019(19) 0.0108(19) 0.000(2) C11 0.024(2) 0.034(3) 0.028(2) -0.0022(19) 0.0068(18) 0.001(2) N12 0.027(2) 0.033(2) 0.0241(17) 0.0011(16) 0.0068(15) 0.0005(18) C13 0.046(3) 0.033(3) 0.028(2) 0.002(2) 0.010(2) 0.000(2) C14 0.037(3) 0.035(3) 0.038(3) 0.000(2) 0.015(2) -0.002(2) C15 0.030(3) 0.039(3) 0.039(3) 0.000(2) 0.011(2) 0.001(2) C16 0.028(2) 0.028(3) 0.028(2) -0.0014(18) 0.0030(18) 0.004(2) C17 0.023(2) 0.031(2) 0.037(2) -0.0006(18) 0.0027(19) 0.003(2) S18 0.0317(11) 0.0296(12) 0.0422(9) -0.0017(8) 0.0051(7) 0.0073(8) C19 0.024(3) 0.034(3) 0.031(3) 0.001(3) -0.004(3) 0.000(2) C20 0.028(3) 0.033(3) 0.036(3) 0.001(2) -0.002(2) 0.003(3) C21 0.028(4) 0.036(4) 0.038(4) 0.004(3) 0.004(4) 0.004(3) S18X 0.027(4) 0.035(4) 0.034(4) 0.001(3) 0.003(3) 0.004(3) _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 O1' C1' 1.412(6) . ? O1' C4' 1.447(5) . ? C1' H1' 1.000 . ? C1' C2' 1.519(6) . ? C1' N1 1.502(6) . ? C2' H2'A 0.990 . ? C2' H2'B 0.990 . ? C2' C3' 1.522(7) . ? C3' H3'A 1.000 . ? C3' O3' 1.435(6) . ? C3' C4' 1.519(6) . ? O3' H3' 0.84(2) . ? C4' H4' 1.000 . ? C4' C5' 1.504(7) . ? C5' H5'A 0.990 . ? C5' H5'B 0.990 . ? C5' O5' 1.433(7) . ? O5' H5' 0.86(2) . ? N1 C2 1.408(6) . ? N1 C6 1.343(6) . ? C2 O2 1.227(6) . ? C2 N3 1.371(6) . ? N3 C4 1.309(6) . ? C4 O4 1.369(5) . ? C4 C5 1.391(6) . ? O4 C8 1.417(5) . ? C5 C6 1.363(6) . ? C5 C7 1.453(6) . ? C6 H6 0.950 . ? C7 H7 0.950 . ? C7 C8 1.322(7) . ? C8 C9 1.478(6) . ? C9 H9A 0.990 . ? C9 H9B 0.990 . ? C9 C10 1.534(6) . ? C10 H10A 0.990 . ? C10 H10B 0.990 . ? C10 C11 1.527(6) . ? C11 H11A 0.990 . ? C11 H11B 0.990 . ? C11 N12 1.464(5) . ? N12 C13 1.367(6) . ? N12 C16 1.368(6) . ? C13 H13 0.950 . ? C13 C14 1.366(7) . ? C14 H14 0.950 . ? C14 C15 1.408(7) . ? C15 H15 0.950 . ? C15 C16 1.391(6) . ? C16 C17 1.460(6) . ? C17 S18 1.712(5) . ? C17 C21 1.358(12) . ? C17 S18X 1.690(10) . ? C17 C21X 1.34(2) . ? S18 C19 1.738(6) . ? C19 H19 0.950 . ? C19 C20 1.345(8) . ? C20 H20 0.950 . ? C20 C21 1.427(16) . ? C21 H21 0.950 . ? S18X C19X 1.739(18) . ? C19X H19X 0.950 . ? C19X C20X 1.342(18) . ? C20X H20X 0.950 . ? C20X C21X 1.43(2) . ? C21X H21X 0.950 . ? 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' O1' C4' 111.3(3) . . ? O1' C1' H1' 109.4 . . ? O1' C1' C2' 106.5(4) . . ? O1' C1' N1 107.5(4) . . ? H1' C1' C2' 109.4 . . ? H1' C1' N1 109.4 . . ? C2' C1' N1 114.4(4) . . ? C1' C2' H2'A 111.4 . . ? C1' C2' H2'B 111.4 . . ? C1' C2' C3' 101.8(4) . . ? H2'A C2' H2'B 109.3 . . ? H2'A C2' C3' 111.4 . . ? H2'B C2' C3' 111.4 . . ? C2' C3' H3'A 111.9 . . ? C2' C3' O3' 111.3(4) . . ? C2' C3' C4' 103.3(4) . . ? H3'A C3' O3' 111.9 . . ? H3'A C3' C4' 111.9 . . ? O3' C3' C4' 106.1(4) . . ? C3' O3' H3' 105(4) . . ? O1' C4' C3' 104.3(4) . . ? O1' C4' H4' 108.2 . . ? O1' C4' C5' 110.5(4) . . ? C3' C4' H4' 108.2 . . ? C3' C4' C5' 117.2(4) . . ? H4' C4' C5' 108.2 . . ? C4' C5' H5'A 109.6 . . ? C4' C5' H5'B 109.6 . . ? C4' C5' O5' 110.3(4) . . ? H5'A C5' H5'B 108.1 . . ? H5'A C5' O5' 109.6 . . ? H5'B C5' O5' 109.6 . . ? C5' O5' H5' 109(4) . . ? C1' N1 C2 115.7(4) . . ? C1' N1 C6 120.2(4) . . ? C2 N1 C6 124.0(4) . . ? N1 C2 O2 119.1(4) . . ? N1 C2 N3 118.6(4) . . ? O2 C2 N3 122.3(4) . . ? C2 N3 C4 114.6(4) . . ? N3 C4 O4 119.8(4) . . ? N3 C4 C5 129.5(4) . . ? O4 C4 C5 110.7(4) . . ? C4 O4 C8 105.1(3) . . ? C4 C5 C6 115.4(4) . . ? C4 C5 C7 105.5(4) . . ? C6 C5 C7 139.1(4) . . ? N1 C6 C5 117.9(4) . . ? N1 C6 H6 121.0 . . ? C5 C6 H6 121.0 . . ? C5 C7 H7 126.5 . . ? C5 C7 C8 107.0(4) . . ? H7 C7 C8 126.5 . . ? O4 C8 C7 111.7(4) . . ? O4 C8 C9 113.5(4) . . ? C7 C8 C9 134.8(4) . . ? C8 C9 H9A 108.9 . . ? C8 C9 H9B 108.9 . . ? C8 C9 C10 113.2(4) . . ? H9A C9 H9B 107.7 . . ? H9A C9 C10 108.9 . . ? H9B C9 C10 108.9 . . ? C9 C10 H10A 109.6 . . ? C9 C10 H10B 109.6 . . ? C9 C10 C11 110.2(4) . . ? H10A C10 H10B 108.1 . . ? H10A C10 C11 109.6 . . ? H10B C10 C11 109.6 . . ? C10 C11 H11A 109.1 . . ? C10 C11 H11B 109.1 . . ? C10 C11 N12 112.7(4) . . ? H11A C11 H11B 107.8 . . ? H11A C11 N12 109.1 . . ? H11B C11 N12 109.1 . . ? C11 N12 C13 122.8(4) . . ? C11 N12 C16 127.4(4) . . ? C13 N12 C16 109.5(3) . . ? N12 C13 H13 125.8 . . ? N12 C13 C14 108.4(4) . . ? H13 C13 C14 125.8 . . ? C13 C14 H14 126.3 . . ? C13 C14 C15 107.5(4) . . ? H14 C14 C15 126.3 . . ? C14 C15 H15 126.3 . . ? C14 C15 C16 107.4(4) . . ? H15 C15 C16 126.3 . . ? N12 C16 C15 107.2(4) . . ? N12 C16 C17 125.1(4) . . ? C15 C16 C17 127.7(4) . . ? C16 C17 S18 118.9(3) . . ? C16 C17 C21 130.8(7) . . ? C16 C17 S18X 126.9(6) . . ? C16 C17 C21X 121.2(12) . . ? S18 C17 C21 110.2(7) . . ? S18X C17 C21X 111.9(11) . . ? C17 S18 C19 91.7(3) . . ? S18 C19 H19 123.8 . . ? S18 C19 C20 112.4(6) . . ? H19 C19 C20 123.8 . . ? C19 C20 H20 124.7 . . ? C19 C20 C21 110.7(8) . . ? H20 C20 C21 124.7 . . ? C17 C21 C20 114.9(10) . . ? C17 C21 H21 122.5 . . ? C20 C21 H21 122.5 . . ? C17 S18X C19X 91.0(10) . . ? S18X C19X H19X 123.7 . . ? S18X C19X C20X 112.5(19) . . ? H19X C19X C20X 123.7 . . ? C19X C20X H20X 124.9 . . ? C19X C20X C21X 110(2) . . ? H20X C20X C21X 124.9 . . ? C17 C21X C20X 114.2(18) . . ? C17 C21X H21X 122.9 . . ? C20X C21X H21X 122.9 . . ? 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 C4' O1' C1' C2' -10.3(5) . . . . ? C4' O1' C1' N1 -133.3(3) . . . . ? O1' C1' C2' C3' 28.6(5) . . . . ? N1 C1' C2' C3' 147.2(4) . . . . ? C1' C2' C3' O3' 78.0(5) . . . . ? C1' C2' C3' C4' -35.4(5) . . . . ? C1' O1' C4' C3' -12.6(5) . . . . ? C1' O1' C4' C5' 114.2(4) . . . . ? C2' C3' C4' O1' 30.0(5) . . . . ? C2' C3' C4' C5' -92.5(5) . . . . ? O3' C3' C4' O1' -87.0(4) . . . . ? O3' C3' C4' C5' 150.4(4) . . . . ? O1' C4' C5' O5' -59.4(5) . . . . ? C3' C4' C5' O5' 59.8(5) . . . . ? O1' C1' N1 C2 -160.0(3) . . . . ? O1' C1' N1 C6 16.3(5) . . . . ? C2' C1' N1 C2 81.9(5) . . . . ? C2' C1' N1 C6 -101.7(5) . . . . ? C1' N1 C2 O2 -0.8(6) . . . . ? C1' N1 C2 N3 177.9(3) . . . . ? C6 N1 C2 O2 -176.9(4) . . . . ? C6 N1 C2 N3 1.8(6) . . . . ? N1 C2 N3 C4 -1.7(6) . . . . ? O2 C2 N3 C4 177.0(4) . . . . ? C2 N3 C4 O4 -179.7(4) . . . . ? C2 N3 C4 C5 -0.6(6) . . . . ? N3 C4 O4 C8 178.0(4) . . . . ? C5 C4 O4 C8 -1.3(4) . . . . ? N3 C4 C5 C6 2.8(7) . . . . ? N3 C4 C5 C7 -178.2(4) . . . . ? O4 C4 C5 C6 -178.0(3) . . . . ? O4 C4 C5 C7 1.0(5) . . . . ? C1' N1 C6 C5 -175.5(4) . . . . ? C2 N1 C6 C5 0.5(6) . . . . ? C4 C5 C6 N1 -2.6(6) . . . . ? C7 C5 C6 N1 178.9(5) . . . . ? C4 C5 C7 C8 -0.3(5) . . . . ? C6 C5 C7 C8 178.3(5) . . . . ? C5 C7 C8 O4 -0.5(5) . . . . ? C5 C7 C8 C9 176.3(5) . . . . ? C4 O4 C8 C7 1.1(4) . . . . ? C4 O4 C8 C9 -176.4(3) . . . . ? O4 C8 C9 C10 54.7(5) . . . . ? C7 C8 C9 C10 -122.1(6) . . . . ? C8 C9 C10 C11 63.6(5) . . . . ? C9 C10 C11 N12 179.3(4) . . . . ? C10 C11 N12 C13 -80.6(5) . . . . ? C10 C11 N12 C16 106.3(5) . . . . ? C11 N12 C13 C14 -172.7(4) . . . . ? C16 N12 C13 C14 1.5(5) . . . . ? N12 C13 C14 C15 -1.5(6) . . . . ? C13 C14 C15 C16 1.0(6) . . . . ? C11 N12 C16 C15 173.0(4) . . . . ? C11 N12 C16 C17 -5.7(7) . . . . ? C13 N12 C16 C15 -0.9(5) . . . . ? C13 N12 C16 C17 -179.6(5) . . . . ? C14 C15 C16 N12 -0.1(5) . . . . ? C14 C15 C16 C17 178.6(5) . . . . ? N12 C16 C17 S18 145.8(4) . . . . ? N12 C16 C17 C21 -36.6(13) . . . . ? N12 C16 C17 S18X -35.0(10) . . . . ? N12 C16 C17 C21X 146(2) . . . . ? C15 C16 C17 S18 -32.6(7) . . . . ? C15 C16 C17 C21 145.0(12) . . . . ? C15 C16 C17 S18X 146.6(9) . . . . ? C15 C16 C17 C21X -33(3) . . . . ? C16 C17 S18 C19 177.3(5) . . . . ? C21 C17 S18 C19 -0.7(9) . . . . ? C17 S18 C19 C20 1.8(8) . . . . ? S18 C19 C20 C21 -2.3(14) . . . . ? C16 C17 C21 C20 -178.2(9) . . . . ? S18 C17 C21 C20 -0.5(17) . . . . ? C19 C20 C21 C17 1.8(19) . . . . ? C16 C17 S18X C19X -179.0(17) . . . . ? C21X C17 S18X C19X 0(3) . . . . ? C17 S18X C19X C20X -3(4) . . . . ? S18X C19X C20X C21X 4(5) . . . . ? C16 C17 C21X C20X -179(3) . . . . ? S18X C17 C21X C20X 2(4) . . . . ? C19X C20X C21X C17 -4(6) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O3' H3' O2 0.84(2) 1.93(2) 2.763(4) 172(6) 2_647 O5' H5' O2 0.86(2) 1.96(3) 2.784(5) 161(6) 1_455 _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 67.16 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.334 _refine_diff_density_min -0.319 _refine_diff_density_rms 0.061 #===END data_ah171_4-amino-1-butyne_hydrochloride_ESI_only _database_code_depnum_ccdc_archive 'CCDC 785465' #TrackingRef 'OBC-Revised-CIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C4 H8 Cl N' _chemical_formula_sum 'C4 H8 Cl N' _chemical_formula_weight 105.56 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/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 10.1580(6) _cell_length_b 5.7057(3) _cell_length_c 11.3236(7) _cell_angle_alpha 90.00 _cell_angle_beta 111.933(7) _cell_angle_gamma 90.00 _cell_volume 608.80(6) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1802 _cell_measurement_theta_min 3.39 _cell_measurement_theta_max 29.18 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.152 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 224 _exptl_absorpt_coefficient_mu 0.492 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.860 _exptl_absorpt_correction_T_max 0.910 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET) (compiled Feb 27 2009,15:38:38) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube with Enhance optics' _diffrn_radiation_monochromator none _diffrn_measurement_device_type 'Oxford Diffraction Gemini A Ultra diffractometer' _diffrn_measurement_method 'thin-slice \w scans' _diffrn_detector_area_resol_mean 10.3968 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2977 _diffrn_reflns_av_R_equivalents 0.0187 _diffrn_reflns_av_sigmaI/netI 0.0282 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.40 _diffrn_reflns_theta_max 29.25 _reflns_number_total 1414 _reflns_number_gt 1128 _reflns_threshold_expression I>2\s(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET) (compiled Feb 27 2009,15:38:38) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET) (compiled Feb 27 2009,15:38:38) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET) (compiled Feb 27 2009,15:38:38) ; _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL and local programs' _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^)+(0.0423P)^2^+0.0000P] 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 1414 _refine_ls_number_parameters 87 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0390 _refine_ls_R_factor_gt 0.0285 _refine_ls_wR_factor_ref 0.0723 _refine_ls_wR_factor_gt 0.0699 _refine_ls_goodness_of_fit_ref 1.010 _refine_ls_restrained_S_all 1.010 _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 Cl Cl 0.13529(3) 0.72456(5) 0.65253(3) 0.02499(13) Uani 1 1 d . . . N N 0.17495(13) 0.2209(2) 0.54824(11) 0.0228(3) Uani 1 1 d . . . H1A H 0.1896(15) 0.346(3) 0.5957(14) 0.030(4) Uiso 1 1 d . . . H1B H 0.0950(19) 0.234(3) 0.4882(18) 0.037(5) Uiso 1 1 d . . . H1C H 0.1739(16) 0.108(3) 0.5970(14) 0.037(4) Uiso 1 1 d . . . C1 C 0.4797(2) 0.3280(4) 0.30988(16) 0.0501(5) Uani 1 1 d . . . H1 H 0.555(2) 0.305(4) 0.278(2) 0.074(7) Uiso 1 1 d . . . C2 C 0.38711(16) 0.3555(3) 0.34710(13) 0.0374(4) Uani 1 1 d . . . C3 C 0.27485(16) 0.3820(3) 0.39809(14) 0.0330(3) Uani 1 1 d . . . H3A H 0.2817(15) 0.524(3) 0.4365(14) 0.041(4) Uiso 1 1 d . . . H3B H 0.1826(16) 0.374(3) 0.3288(14) 0.037(4) Uiso 1 1 d . . . C4 C 0.28559(15) 0.1907(3) 0.49381(13) 0.0263(3) Uani 1 1 d . . . H4A H 0.2713(14) 0.046(3) 0.4534(13) 0.030(4) Uiso 1 1 d . . . H4B H 0.3772(18) 0.197(3) 0.5665(16) 0.036(4) Uiso 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 Cl 0.02424(19) 0.02138(19) 0.02322(19) -0.00046(11) 0.00181(12) 0.00097(12) N 0.0224(6) 0.0237(6) 0.0200(6) 0.0005(5) 0.0052(5) -0.0003(5) C1 0.0470(10) 0.0701(14) 0.0394(10) -0.0028(8) 0.0234(8) -0.0150(10) C2 0.0395(9) 0.0448(10) 0.0287(8) 0.0003(6) 0.0138(7) -0.0108(7) C3 0.0351(8) 0.0327(9) 0.0316(8) 0.0060(6) 0.0130(6) 0.0009(7) C4 0.0261(7) 0.0279(8) 0.0265(7) 0.0023(5) 0.0115(6) 0.0037(6) _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 N H1A 0.874(16) . ? N H1B 0.845(19) . ? N H1C 0.851(17) . ? N C4 1.4798(18) . ? C1 H1 0.96(2) . ? C1 C2 1.176(2) . ? C2 C3 1.466(2) . ? C3 H3A 0.909(17) . ? C3 H3B 0.973(15) . ? C3 C4 1.513(2) . ? C4 H4A 0.928(16) . ? C4 H4B 0.986(17) . ? 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 H1A N H1B 108.4(14) . . ? H1A N H1C 105.2(15) . . ? H1A N C4 111.7(10) . . ? H1B N H1C 110.2(15) . . ? H1B N C4 109.0(12) . . ? H1C N C4 112.2(10) . . ? H1 C1 C2 179.2(13) . . ? C1 C2 C3 177.39(18) . . ? C2 C3 H3A 110.4(10) . . ? C2 C3 H3B 109.5(8) . . ? C2 C3 C4 110.44(13) . . ? H3A C3 H3B 107.8(14) . . ? H3A C3 C4 109.1(10) . . ? H3B C3 C4 109.6(10) . . ? N C4 C3 110.58(12) . . ? N C4 H4A 107.8(9) . . ? N C4 H4B 106.0(9) . . ? C3 C4 H4A 109.4(9) . . ? C3 C4 H4B 111.4(9) . . ? H4A C4 H4B 111.6(13) . . ? 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 C2 C3 C4 N 178.37(12) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N H1A Cl 0.874(16) 2.374(16) 3.1892(13) 155.2(13) . N H1B Cl 0.845(19) 2.299(19) 3.1376(13) 171.8(16) 3_566 N H1C Cl 0.851(17) 2.349(17) 3.1516(13) 157.2(13) 1_545 _diffrn_measured_fraction_theta_max 0.855 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.273 _refine_diff_density_min -0.177 _refine_diff_density_rms 0.048 #===END