# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_qian1molt _database_code_depnum_ccdc_archive 'CCDC 902390' #TrackingRef '14112_web_deposit_cif_file_0_JianweiSun_1348151518.qian1molt.cif' _audit_creation_date 2012-05-15 _audit_creation_method ; Olex2 1.2-beta (compiled May 9 2012 12:37:22, GUI svn.r4230) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C23 H21 N O4 S' _chemical_formula_sum 'C23 H21 N O4 S' _chemical_formula_weight 407.47 _chemical_melting_point ? 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c _space_group_IT_number 15 _space_group_name_Hall '-C 2yc' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y, -z+1/2' 3 'x+1/2, y+1/2, z' 4 '-x+1/2, y+1/2, -z+1/2' 5 '-x, -y, -z' 6 'x, -y, z-1/2' 7 '-x+1/2, -y+1/2, -z' 8 'x+1/2, -y+1/2, z-1/2' _cell_length_a 17.9255(5) _cell_length_b 9.5117(2) _cell_length_c 24.5699(8) _cell_angle_alpha 90.00 _cell_angle_beta 102.966(3) _cell_angle_gamma 90.00 _cell_volume 4082.41(19) _cell_formula_units_Z 8 _cell_measurement_reflns_used 3752 _cell_measurement_temperature 173.00(14) _cell_measurement_theta_max 28.2630 _cell_measurement_theta_min 3.1337 _exptl_absorpt_coefficient_mu 0.188 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.97783 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.326 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 1712 _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.24 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0327 _diffrn_reflns_av_unetI/netI 0.0452 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_number 11559 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 26.99 _diffrn_reflns_theta_min 3.34 _diffrn_ambient_temperature 173.00(14) _diffrn_detector_area_resol_mean 15.9578 _diffrn_measured_fraction_theta_full 0.992 _diffrn_measured_fraction_theta_max 0.979 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -98.00 7.60 0.8000 5.0000 omega____ theta____ kappa____ phi______ frames - -25.1205 -57.0000 -150.0000 132 #__ type_ start__ end____ width___ exp.time_ 2 omega -115.00 -35.80 0.8000 5.0000 omega____ theta____ kappa____ phi______ frames - -25.1205 -178.0000 -60.0000 99 #__ type_ start__ end____ width___ exp.time_ 3 omega -29.00 53.40 0.8000 5.0000 omega____ theta____ kappa____ phi______ frames - -25.1205 38.0000 0.0000 103 #__ type_ start__ end____ width___ exp.time_ 4 omega -51.00 62.60 0.8000 5.0000 omega____ theta____ kappa____ phi______ frames - 25.5892 -77.0000 120.0000 142 ; _diffrn_measurement_device 'kappa diffractometer' _diffrn_measurement_device_type 'Xcalibur, Sapphire3, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0078776000 _diffrn_orient_matrix_UB_12 -0.0266130000 _diffrn_orient_matrix_UB_13 -0.0250948000 _diffrn_orient_matrix_UB_21 -0.0392476000 _diffrn_orient_matrix_UB_22 -0.0169135000 _diffrn_orient_matrix_UB_23 -0.0097905000 _diffrn_orient_matrix_UB_31 -0.0067337000 _diffrn_orient_matrix_UB_32 0.0675855000 _diffrn_orient_matrix_UB_33 -0.0123379000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.7107 _diffrn_source 'sealed X-ray tube' _diffrn_source_current 40 _diffrn_source_power 2.0 _diffrn_source_target Mo _diffrn_source_voltage 50 _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 3700 _reflns_number_total 4353 _reflns_odcompleteness_completeness 99.67 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; XL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; XS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 0.287 _refine_diff_density_min -0.332 _refine_diff_density_rms 0.047 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.005 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 264 _refine_ls_number_reflns 4353 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0588 _refine_ls_R_factor_gt 0.0480 _refine_ls_restrained_S_all 1.005 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0433P)^2^+2.3791P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1015 _refine_ls_wR_factor_ref 0.1079 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.15167(3) 0.43669(4) 0.312497(18) 0.02524(13) Uani 1 1 d . . . O3 O 0.23496(7) 1.06150(12) 0.29868(5) 0.0270(3) Uani 1 1 d . . . H3 H 0.2177 1.1437 0.2978 0.040 Uiso 1 1 calc R . . O4 O 0.19379(7) 0.78264(14) 0.41005(5) 0.0306(3) Uani 1 1 d . . . O2 O 0.07589(7) 0.44843(14) 0.32153(6) 0.0351(3) Uani 1 1 d . . . O1 O 0.17034(8) 0.32226(13) 0.27933(5) 0.0324(3) Uani 1 1 d . . . N1 N 0.17105(9) 0.57504(15) 0.28146(6) 0.0263(3) Uani 1 1 d . . . H1 H 0.1982 0.5661 0.2559 0.032 Uiso 1 1 calc R . . C1 C 0.14609(9) 0.71492(18) 0.29322(7) 0.0214(4) Uani 1 1 d . . . H1A H 0.1116 0.7059 0.3199 0.026 Uiso 1 1 calc R . . C2 C 0.21136(9) 0.81767(17) 0.31848(7) 0.0201(3) Uani 1 1 d . . . H2 H 0.2550 0.8029 0.2999 0.024 Uiso 1 1 calc R . . C3 C 0.17596(9) 0.96390(17) 0.30227(7) 0.0217(4) Uani 1 1 d . . . H3A H 0.1481 0.9963 0.3310 0.026 Uiso 1 1 calc R . . C4 C 0.11942(10) 0.93573(18) 0.24790(7) 0.0240(4) Uani 1 1 d . . . C5 C 0.10353(9) 0.79319(19) 0.24205(7) 0.0229(4) Uani 1 1 d . . . C6 C 0.05237(10) 0.7421(2) 0.19543(7) 0.0306(4) Uani 1 1 d . . . H6 H 0.0416 0.6445 0.1912 0.037 Uiso 1 1 calc R . . C7 C 0.01721(11) 0.8381(2) 0.15497(8) 0.0369(5) Uani 1 1 d . . . H7 H -0.0180 0.8053 0.1226 0.044 Uiso 1 1 calc R . . C8 C 0.03265(11) 0.9802(2) 0.16117(8) 0.0389(5) Uani 1 1 d . . . H8 H 0.0079 1.0438 0.1330 0.047 Uiso 1 1 calc R . . C9 C 0.08378(11) 1.0314(2) 0.20794(8) 0.0329(4) Uani 1 1 d . . . H9 H 0.0940 1.1292 0.2124 0.039 Uiso 1 1 calc R . . C10 C 0.24012(10) 0.80238(17) 0.38130(7) 0.0217(4) Uani 1 1 d . . . C11 C 0.32336(10) 0.81553(18) 0.40723(7) 0.0234(4) Uani 1 1 d . . . C12 C 0.34849(11) 0.7824(2) 0.46357(7) 0.0325(4) Uani 1 1 d . . . H12 H 0.3130 0.7492 0.4841 0.039 Uiso 1 1 calc R . . C13 C 0.42454(12) 0.7977(2) 0.48968(8) 0.0416(5) Uani 1 1 d . . . H13 H 0.4413 0.7749 0.5281 0.050 Uiso 1 1 calc R . . C14 C 0.47659(11) 0.8462(2) 0.46031(8) 0.0400(5) Uani 1 1 d . . . H14 H 0.5289 0.8576 0.4786 0.048 Uiso 1 1 calc R . . C15 C 0.45248(12) 0.8779(3) 0.40437(9) 0.0442(5) Uani 1 1 d . . . H15 H 0.4883 0.9103 0.3840 0.053 Uiso 1 1 calc R . . C16 C 0.37612(11) 0.8626(2) 0.37790(8) 0.0351(5) Uani 1 1 d . . . H16 H 0.3598 0.8845 0.3393 0.042 Uiso 1 1 calc R . . C21 C 0.21472(11) 0.42545(18) 0.37873(7) 0.0276(4) Uani 1 1 d . . . C22 C 0.18812(12) 0.4505(2) 0.42660(8) 0.0379(5) Uani 1 1 d . . . H22 H 0.1357 0.4723 0.4240 0.046 Uiso 1 1 calc R . . C23 C 0.23820(14) 0.4437(2) 0.47805(9) 0.0450(6) Uani 1 1 d . . . H23 H 0.2195 0.4591 0.5108 0.054 Uiso 1 1 calc R . . C24 C 0.31502(14) 0.4147(2) 0.48306(9) 0.0438(5) Uani 1 1 d . . . C25 C 0.34057(13) 0.3896(3) 0.43502(9) 0.0498(6) Uani 1 1 d . . . H25 H 0.3930 0.3684 0.4377 0.060 Uiso 1 1 calc R . . C26 C 0.29083(12) 0.3947(2) 0.38292(9) 0.0418(5) Uani 1 1 d . . . H26 H 0.3092 0.3770 0.3502 0.050 Uiso 1 1 calc R . . C27 C 0.36983(17) 0.4153(3) 0.53950(10) 0.0643(8) Uani 1 1 d . . . H27A H 0.3706 0.5091 0.5562 0.096 Uiso 1 1 calc R . . H27B H 0.4213 0.3912 0.5351 0.096 Uiso 1 1 calc R . . H27C H 0.3531 0.3462 0.5638 0.096 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 0.0304(2) 0.0174(2) 0.0283(2) 0.00053(17) 0.00745(18) -0.00118(18) O3 0.0316(7) 0.0171(6) 0.0328(7) -0.0001(5) 0.0084(6) -0.0025(5) O4 0.0310(7) 0.0403(8) 0.0225(6) 0.0016(6) 0.0099(5) -0.0015(6) O2 0.0305(7) 0.0315(8) 0.0453(8) 0.0063(6) 0.0126(6) -0.0040(6) O1 0.0464(8) 0.0176(7) 0.0319(7) -0.0031(5) 0.0058(6) 0.0012(6) N1 0.0359(8) 0.0184(8) 0.0285(8) -0.0007(6) 0.0157(7) 0.0012(6) C1 0.0245(8) 0.0186(9) 0.0220(8) -0.0013(7) 0.0074(7) 0.0009(7) C2 0.0219(8) 0.0188(9) 0.0201(8) 0.0005(6) 0.0059(6) 0.0008(7) C3 0.0247(9) 0.0180(9) 0.0228(8) 0.0009(7) 0.0062(7) 0.0011(7) C4 0.0254(9) 0.0249(9) 0.0219(8) 0.0006(7) 0.0059(7) 0.0020(7) C5 0.0226(8) 0.0258(9) 0.0214(8) -0.0005(7) 0.0071(7) -0.0002(7) C6 0.0294(10) 0.0339(11) 0.0284(9) -0.0042(8) 0.0061(7) -0.0067(8) C7 0.0294(10) 0.0537(14) 0.0241(9) -0.0014(9) -0.0012(8) -0.0067(9) C8 0.0358(11) 0.0461(13) 0.0308(10) 0.0118(9) -0.0011(8) 0.0060(10) C9 0.0361(10) 0.0289(11) 0.0315(10) 0.0054(8) 0.0031(8) 0.0039(8) C10 0.0284(9) 0.0171(9) 0.0204(8) 0.0007(6) 0.0070(7) 0.0022(7) C11 0.0267(9) 0.0210(9) 0.0220(8) 0.0008(7) 0.0042(7) 0.0024(7) C12 0.0359(10) 0.0376(11) 0.0239(9) 0.0041(8) 0.0068(8) 0.0006(9) C13 0.0417(12) 0.0529(14) 0.0249(10) 0.0045(9) -0.0037(9) 0.0038(10) C14 0.0275(10) 0.0498(13) 0.0379(11) -0.0036(10) -0.0030(8) 0.0008(9) C15 0.0300(11) 0.0609(15) 0.0417(12) 0.0066(11) 0.0078(9) -0.0058(10) C16 0.0306(10) 0.0479(13) 0.0256(9) 0.0058(9) 0.0039(8) -0.0034(9) C21 0.0367(10) 0.0198(9) 0.0273(9) 0.0008(7) 0.0091(8) 0.0009(8) C22 0.0456(12) 0.0377(12) 0.0339(11) -0.0011(9) 0.0161(9) 0.0060(10) C23 0.0674(15) 0.0415(13) 0.0278(10) -0.0011(9) 0.0143(10) 0.0112(11) C24 0.0643(15) 0.0301(11) 0.0309(11) -0.0028(9) -0.0019(10) 0.0138(10) C25 0.0428(13) 0.0638(16) 0.0385(12) -0.0069(11) 0.0003(10) 0.0158(12) C26 0.0379(11) 0.0560(14) 0.0321(11) -0.0042(10) 0.0093(9) 0.0086(10) C27 0.0869(19) 0.0572(17) 0.0373(13) -0.0109(12) -0.0103(12) 0.0269(14) _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 O2 1.4290(13) . ? S1 O1 1.4433(13) . ? S1 N1 1.5978(15) . ? S1 C21 1.7640(19) . ? O3 C3 1.425(2) . ? O4 C10 1.2196(19) . ? N1 C1 1.453(2) . ? C1 C2 1.544(2) . ? C1 C5 1.512(2) . ? C2 C3 1.544(2) . ? C2 C10 1.521(2) . ? C3 C4 1.509(2) . ? C4 C5 1.386(2) . ? C4 C9 1.385(2) . ? C5 C6 1.385(2) . ? C6 C7 1.392(3) . ? C7 C8 1.382(3) . ? C8 C9 1.387(3) . ? C10 C11 1.490(2) . ? C11 C12 1.392(2) . ? C11 C16 1.385(2) . ? C12 C13 1.378(3) . ? C13 C14 1.380(3) . ? C14 C15 1.378(3) . ? C15 C16 1.385(3) . ? C21 C22 1.385(3) . ? C21 C26 1.376(3) . ? C22 C23 1.378(3) . ? C23 C24 1.382(3) . ? C24 C25 1.379(3) . ? C24 C27 1.509(3) . ? C25 C26 1.387(3) . ? 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 O2 S1 O1 119.71(8) . . ? O2 S1 N1 109.02(8) . . ? O2 S1 C21 107.22(8) . . ? O1 S1 N1 104.41(8) . . ? O1 S1 C21 107.06(8) . . ? N1 S1 C21 109.10(8) . . ? C1 N1 S1 123.34(12) . . ? N1 C1 C2 114.84(14) . . ? N1 C1 C5 113.95(14) . . ? C5 C1 C2 102.59(13) . . ? C3 C2 C1 103.66(13) . . ? C10 C2 C1 113.66(13) . . ? C10 C2 C3 111.97(13) . . ? O3 C3 C2 109.58(13) . . ? O3 C3 C4 114.92(14) . . ? C4 C3 C2 102.94(13) . . ? C5 C4 C3 110.31(15) . . ? C9 C4 C3 128.49(16) . . ? C9 C4 C5 121.17(17) . . ? C4 C5 C1 109.98(14) . . ? C6 C5 C1 129.20(17) . . ? C6 C5 C4 120.75(17) . . ? C5 C6 C7 118.09(18) . . ? C8 C7 C6 121.02(18) . . ? C7 C8 C9 120.89(18) . . ? C4 C9 C8 118.07(19) . . ? O4 C10 C2 118.87(15) . . ? O4 C10 C11 120.79(15) . . ? C11 C10 C2 120.31(14) . . ? C12 C11 C10 118.39(15) . . ? C16 C11 C10 122.65(15) . . ? C16 C11 C12 118.93(16) . . ? C13 C12 C11 120.30(18) . . ? C12 C13 C14 120.40(18) . . ? C15 C14 C13 119.79(18) . . ? C14 C15 C16 120.06(19) . . ? C15 C16 C11 120.52(18) . . ? C22 C21 S1 120.10(15) . . ? C26 C21 S1 120.06(14) . . ? C26 C21 C22 119.82(18) . . ? C23 C22 C21 119.5(2) . . ? C22 C23 C24 121.5(2) . . ? C23 C24 C27 120.8(2) . . ? C25 C24 C23 118.27(19) . . ? C25 C24 C27 121.0(2) . . ? C24 C25 C26 121.0(2) . . ? C21 C26 C25 119.84(19) . . ? 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 O1 0.84 1.91 2.7336(17) 167.8 1_565 N1 H1 O3 0.88 1.99 2.8671(18) 174.7 4_545 data_qian4cult _database_code_depnum_ccdc_archive 'CCDC 902391' #TrackingRef '14113_web_deposit_cif_file_1_JianweiSun_1348151518.qian4cult.cif' _audit_creation_date 2012-09-07 _audit_creation_method ; Olex2 1.2-beta (compiled May 9 2012 12:37:22, GUI svn.r4230) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C20 H19 N O2 S' _chemical_formula_sum 'C20 H19 N O2 S' _chemical_formula_weight 337.42 _chemical_absolute_configuration ad _chemical_melting_point ? 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 Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) _space_group_IT_number 19 _space_group_name_Hall 'P 2ac 2ab' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, -y, z+1/2' 3 'x+1/2, -y+1/2, -z' 4 '-x, y+1/2, -z+1/2' _cell_length_a 5.2087(2) _cell_length_b 10.6761(4) _cell_length_c 31.3923(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1745.68(11) _cell_formula_units_Z 4 _cell_measurement_reflns_used 4086 _cell_measurement_temperature 173.00(14) _cell_measurement_theta_max 71.8827 _cell_measurement_theta_min 4.1364 _exptl_absorpt_coefficient_mu 1.733 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.60637 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.284 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 712 _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.25 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0292 _diffrn_reflns_av_unetI/netI 0.0349 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 37 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_number 6109 _diffrn_reflns_theta_full 66.50 _diffrn_reflns_theta_max 67.50 _diffrn_reflns_theta_min 4.37 _diffrn_ambient_temperature 173.00(14) _diffrn_detector_area_resol_mean 15.9578 _diffrn_measured_fraction_theta_full 0.9715 _diffrn_measured_fraction_theta_max 0.9715 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega 124.00 149.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 114.0000 -25.0000 30.0000 25 #__ type_ start__ end____ width___ exp.time_ 2 omega 17.00 43.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 0.0000 -99.0000 -180.0000 26 #__ type_ start__ end____ width___ exp.time_ 3 omega -24.00 6.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 0.0000 -99.0000 -180.0000 30 #__ type_ start__ end____ width___ exp.time_ 4 omega 88.00 128.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 57.0000 125.0000 -150.0000 40 #__ type_ start__ end____ width___ exp.time_ 5 omega 74.00 128.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 57.0000 125.0000 60.0000 54 #__ type_ start__ end____ width___ exp.time_ 6 omega 77.00 122.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 57.0000 125.0000 150.0000 45 #__ type_ start__ end____ width___ exp.time_ 7 omega 81.00 107.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 57.0000 84.0000 -34.0000 26 #__ type_ start__ end____ width___ exp.time_ 8 omega -155.00 -135.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - -86.0000 -111.0000 120.0000 20 #__ type_ start__ end____ width___ exp.time_ 9 omega 61.00 157.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 114.0000 145.0000 19.0000 96 #__ type_ start__ end____ width___ exp.time_ 10 omega 45.00 71.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 114.0000 -38.0000 -90.0000 26 #__ type_ start__ end____ width___ exp.time_ 11 omega 88.00 178.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 114.0000 50.0000 -150.0000 90 #__ type_ start__ end____ width___ exp.time_ 12 omega -72.00 33.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 0.0000 -77.0000 -60.0000 105 #__ type_ start__ end____ width___ exp.time_ 13 omega -130.00 -26.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - -57.0000 -38.0000 150.0000 104 #__ type_ start__ end____ width___ exp.time_ 14 omega -128.00 -33.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - -57.0000 -57.0000 60.0000 95 #__ type_ start__ end____ width___ exp.time_ 15 omega -128.00 -87.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - -57.0000 -57.0000 -60.0000 41 #__ type_ start__ end____ width___ exp.time_ 16 omega -116.00 -12.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - -86.0000 111.0000 120.0000 104 #__ type_ start__ end____ width___ exp.time_ 17 omega 124.00 158.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 114.0000 -25.0000 60.0000 34 #__ type_ start__ end____ width___ exp.time_ 18 omega 41.00 52.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 114.0000 -38.0000 -120.0000 11 ; _diffrn_measurement_device 'kappa diffractometer' _diffrn_measurement_device_type 'Xcalibur, Sapphire3, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.2934083000 _diffrn_orient_matrix_UB_12 0.0164313000 _diffrn_orient_matrix_UB_13 0.0031959000 _diffrn_orient_matrix_UB_21 0.0329559000 _diffrn_orient_matrix_UB_22 -0.0675525000 _diffrn_orient_matrix_UB_23 -0.0430659000 _diffrn_orient_matrix_UB_31 -0.0201131000 _diffrn_orient_matrix_UB_32 0.1263999000 _diffrn_orient_matrix_UB_33 -0.0232876000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.5418 _diffrn_source 'sealed X-ray tube' _diffrn_source_current 35 _diffrn_source_power 1.75 _diffrn_source_target Cu _diffrn_source_voltage 50 _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 2721 _reflns_number_total 2795 _reflns_odcompleteness_completeness 97.15 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 68.13 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; XL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; XS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 0.233 _refine_diff_density_min -0.218 _refine_diff_density_rms 0.039 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.01(2) _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 216 _refine_ls_number_reflns 2795 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0412 _refine_ls_R_factor_gt 0.0403 _refine_ls_restrained_S_all 1.002 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0320P)^2^+0.9625P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0922 _refine_ls_wR_factor_ref 0.0930 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.12333(15) 0.56986(9) 0.30434(2) 0.0532(2) Uani 1 1 d . . . O1 O 0.3079(3) 0.29064(18) 0.49013(6) 0.0404(4) Uani 1 1 d . . . H1 H 0.1709 0.2529 0.4960 0.061 Uiso 1 1 calc R . . O2 O -0.1000(3) 0.29493(19) 0.38206(6) 0.0489(5) Uani 1 1 d . . . N1 N 0.4723(4) 0.4354(2) 0.34599(6) 0.0340(5) Uani 1 1 d . . . H1A H 0.6160 0.3922 0.3453 0.041 Uiso 1 1 calc R . . C1 C 0.3516(4) 0.4545(2) 0.38713(7) 0.0318(5) Uani 1 1 d . . . H1B H 0.1819 0.4964 0.3828 0.038 Uiso 1 1 calc R . . C2 C 0.5067(5) 0.5294(2) 0.41879(7) 0.0305(5) Uani 1 1 d . . . C3 C 0.4471(4) 0.4872(2) 0.45980(7) 0.0305(5) Uani 1 1 d . . . C4 C 0.2601(4) 0.3807(2) 0.45764(7) 0.0310(5) Uani 1 1 d . . . H4 H 0.0804 0.4130 0.4600 0.037 Uiso 1 1 calc R . . C5 C 0.3103(4) 0.3317(2) 0.41204(7) 0.0316(5) Uani 1 1 d . . . H5 H 0.4755 0.2839 0.4121 0.038 Uiso 1 1 calc R . . C6 C 0.6898(5) 0.6207(2) 0.41212(7) 0.0335(5) Uani 1 1 d . . . H6 H 0.7314 0.6478 0.3841 0.040 Uiso 1 1 calc R . . C7 C 0.8114(5) 0.6719(3) 0.44731(8) 0.0374(6) Uani 1 1 d . . . H7 H 0.9387 0.7345 0.4434 0.045 Uiso 1 1 calc R . . C8 C 0.7495(5) 0.6327(2) 0.48832(8) 0.0384(6) Uani 1 1 d . . . H8 H 0.8340 0.6695 0.5120 0.046 Uiso 1 1 calc R . . C9 C 0.5666(5) 0.5408(2) 0.49498(7) 0.0354(6) Uani 1 1 d . . . H9 H 0.5235 0.5148 0.5230 0.043 Uiso 1 1 calc R . . C10 C 0.1037(5) 0.2488(2) 0.39321(7) 0.0337(5) Uani 1 1 d . . . C11 C 0.1523(4) 0.1118(2) 0.38796(7) 0.0327(5) Uani 1 1 d . . . C12 C -0.0164(5) 0.0415(3) 0.36309(8) 0.0411(6) Uani 1 1 d . . . H12 H -0.1597 0.0812 0.3501 0.049 Uiso 1 1 calc R . . C13 C 0.0226(6) -0.0848(3) 0.35711(9) 0.0467(7) Uani 1 1 d . . . H13 H -0.0933 -0.1319 0.3401 0.056 Uiso 1 1 calc R . . C14 C 0.2309(6) -0.1428(3) 0.37595(9) 0.0468(7) Uani 1 1 d . . . H14 H 0.2585 -0.2298 0.3716 0.056 Uiso 1 1 calc R . . C15 C 0.3985(6) -0.0755(3) 0.40096(8) 0.0429(6) Uani 1 1 d . . . H15 H 0.5398 -0.1161 0.4142 0.052 Uiso 1 1 calc R . . C16 C 0.3600(5) 0.0516(3) 0.40668(8) 0.0386(6) Uani 1 1 d . . . H16 H 0.4771 0.0983 0.4236 0.046 Uiso 1 1 calc R . . C20 C 0.3811(5) 0.4787(3) 0.30910(8) 0.0396(6) Uani 1 1 d . B . C21 C 0.5307(6) 0.4347(4) 0.27160(8) 0.0573(9) Uani 1 1 d . . . H21A H 0.6935 0.3887 0.2779 0.069 Uiso 0.50 1 calc PR A 2 H21 H 0.7089 0.4049 0.2778 0.069 Uiso 0.50 1 calc PR A 1 C22A C 0.4016(15) 0.4018(8) 0.2318(2) 0.0530(17) Uiso 0.50 1 d P B 2 H22A H 0.2116 0.4031 0.2318 0.064 Uiso 0.50 1 calc PR B 2 H22B H 0.4773 0.3330 0.2148 0.064 Uiso 0.50 1 calc PR B 2 C22 C 0.3707(15) 0.3526(7) 0.2375(2) 0.0503(17) Uiso 0.50 1 d P B 1 H22C H 0.4544 0.2779 0.2249 0.060 Uiso 0.50 1 calc PR B 1 H22D H 0.1821 0.3468 0.2409 0.060 Uiso 0.50 1 calc PR B 1 C23 C 0.4855(14) 0.4779(8) 0.2288(2) 0.0470(16) Uiso 0.50 1 d P B 1 H23A H 0.6352 0.4805 0.2094 0.056 Uiso 0.50 1 calc PR B 1 H23B H 0.3651 0.5489 0.2252 0.056 Uiso 0.50 1 calc PR B 1 C23A C 0.5349(15) 0.5246(8) 0.2306(2) 0.058(2) Uiso 0.50 1 d P B 2 H23C H 0.4289 0.6015 0.2313 0.070 Uiso 0.50 1 calc PR B 2 H23D H 0.6965 0.5309 0.2142 0.070 Uiso 0.50 1 calc PR B 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 S1 0.0462(4) 0.0760(5) 0.0374(3) 0.0054(3) -0.0050(3) 0.0186(4) O1 0.0305(8) 0.0465(11) 0.0442(9) 0.0183(8) -0.0018(8) -0.0035(9) O2 0.0254(8) 0.0499(12) 0.0713(12) 0.0017(10) -0.0087(9) 0.0071(10) N1 0.0244(9) 0.0456(12) 0.0321(10) -0.0029(9) 0.0020(8) 0.0061(10) C1 0.0257(10) 0.0384(13) 0.0313(11) 0.0049(10) 0.0009(10) 0.0043(11) C2 0.0280(11) 0.0332(13) 0.0303(11) 0.0023(10) 0.0018(9) 0.0070(11) C3 0.0247(11) 0.0323(12) 0.0346(12) 0.0026(10) 0.0031(9) 0.0070(10) C4 0.0254(11) 0.0354(13) 0.0323(12) 0.0080(10) 0.0011(9) 0.0053(11) C5 0.0231(11) 0.0325(12) 0.0392(12) 0.0026(10) -0.0012(10) 0.0034(11) C6 0.0365(13) 0.0302(12) 0.0337(12) 0.0055(10) 0.0052(10) 0.0048(12) C7 0.0381(13) 0.0315(13) 0.0425(13) 0.0015(11) 0.0026(11) 0.0008(12) C8 0.0405(14) 0.0343(14) 0.0403(13) -0.0046(11) -0.0022(11) 0.0016(12) C9 0.0357(12) 0.0412(14) 0.0294(11) 0.0009(10) 0.0022(10) 0.0044(12) C10 0.0235(10) 0.0440(14) 0.0337(12) 0.0021(10) -0.0006(10) 0.0022(12) C11 0.0266(11) 0.0407(13) 0.0309(11) 0.0019(10) 0.0037(10) -0.0012(11) C12 0.0344(13) 0.0513(17) 0.0375(13) 0.0045(12) -0.0017(11) -0.0036(13) C13 0.0543(17) 0.0446(17) 0.0413(14) -0.0042(13) 0.0004(13) -0.0121(15) C14 0.0559(17) 0.0385(15) 0.0461(15) -0.0001(12) 0.0162(14) -0.0041(14) C15 0.0402(13) 0.0388(14) 0.0498(15) 0.0062(12) 0.0045(12) 0.0044(14) C16 0.0334(12) 0.0423(15) 0.0402(12) 0.0038(11) -0.0005(11) -0.0010(13) C20 0.0319(12) 0.0538(16) 0.0331(12) -0.0023(11) -0.0026(11) -0.0032(13) C21 0.0446(15) 0.095(3) 0.0321(13) -0.0105(15) 0.0017(12) 0.0069(18) _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 C20 1.665(3) . ? O1 C4 1.424(3) . ? O2 C10 1.221(3) . ? N1 C1 1.451(3) . ? N1 C20 1.334(3) . ? C1 C2 1.509(3) . ? C1 C5 1.542(3) . ? C2 C3 1.399(3) . ? C2 C6 1.380(4) . ? C3 C4 1.499(3) . ? C3 C9 1.391(3) . ? C4 C5 1.547(3) . ? C5 C10 1.513(3) . ? C6 C7 1.386(4) . ? C7 C8 1.391(4) . ? C8 C9 1.384(4) . ? C10 C11 1.493(4) . ? C11 C12 1.394(4) . ? C11 C16 1.389(3) . ? C12 C13 1.376(4) . ? C13 C14 1.382(4) . ? C14 C15 1.377(4) . ? C15 C16 1.384(4) . ? C20 C21 1.488(4) . ? C21 C22A 1.462(7) . ? C21 C22 1.616(7) . ? C21 C23 1.440(7) . ? C21 C23A 1.604(8) . ? C22A C23A 1.484(11) . ? C22 C23 1.490(10) . ? 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 C20 N1 C1 124.8(2) . . ? N1 C1 C2 115.4(2) . . ? N1 C1 C5 113.1(2) . . ? C2 C1 C5 101.02(17) . . ? C3 C2 C1 108.5(2) . . ? C6 C2 C1 130.1(2) . . ? C6 C2 C3 121.4(2) . . ? C2 C3 C4 110.3(2) . . ? C9 C3 C2 119.9(2) . . ? C9 C3 C4 129.7(2) . . ? O1 C4 C3 111.50(18) . . ? O1 C4 C5 113.9(2) . . ? C3 C4 C5 100.88(18) . . ? C1 C5 C4 101.82(19) . . ? C10 C5 C1 113.50(19) . . ? C10 C5 C4 116.05(19) . . ? C2 C6 C7 118.3(2) . . ? C6 C7 C8 120.9(2) . . ? C9 C8 C7 120.8(2) . . ? C8 C9 C3 118.7(2) . . ? O2 C10 C5 119.6(2) . . ? O2 C10 C11 120.7(2) . . ? C11 C10 C5 119.7(2) . . ? C12 C11 C10 118.8(2) . . ? C16 C11 C10 122.6(2) . . ? C16 C11 C12 118.6(3) . . ? C13 C12 C11 120.7(3) . . ? C12 C13 C14 119.8(3) . . ? C15 C14 C13 120.5(3) . . ? C14 C15 C16 119.6(3) . . ? C15 C16 C11 120.8(3) . . ? N1 C20 S1 124.55(19) . . ? N1 C20 C21 113.0(2) . . ? C21 C20 S1 122.4(2) . . ? C20 C21 C22 115.2(3) . . ? C20 C21 C23A 116.9(4) . . ? C22A C21 C20 120.7(4) . . ? C22A C21 C22 20.9(3) . . ? C22A C21 C23A 57.7(4) . . ? C23 C21 C20 123.5(4) . . ? C23 C21 C22A 37.3(3) . . ? C23 C21 C22 58.0(4) . . ? C23 C21 C23A 20.4(4) . . ? C23A C21 C22 78.5(4) . . ? C21 C22A C23A 66.0(5) . . ? C23 C22 C21 55.0(4) . . ? C21 C23 C22 66.9(4) . . ? C22A C23A C21 56.3(4) . . ? 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 O1 H1 O1 0.84 2.00 2.8142(13) 164.7 3_456 N1 H1A O2 0.88 2.14 2.915(3) 145.9 1_655 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 S1 C20 C21 C22A -36.8(6) . . . . ? S1 C20 C21 C22 -59.7(5) . . . . ? S1 C20 C21 C23 7.4(6) . . . . ? S1 C20 C21 C23A 29.8(5) . . . . ? O1 C4 C5 C1 -158.09(18) . . . . ? O1 C4 C5 C10 78.1(3) . . . . ? O2 C10 C11 C12 11.9(4) . . . . ? O2 C10 C11 C16 -168.5(2) . . . . ? N1 C1 C2 C3 -149.0(2) . . . . ? N1 C1 C2 C6 27.8(4) . . . . ? N1 C1 C5 C4 163.79(18) . . . . ? N1 C1 C5 C10 -70.7(3) . . . . ? N1 C20 C21 C22A 141.9(5) . . . . ? N1 C20 C21 C22 119.1(4) . . . . ? N1 C20 C21 C23 -173.9(5) . . . . ? N1 C20 C21 C23A -151.4(4) . . . . ? C1 N1 C20 S1 4.2(4) . . . . ? C1 N1 C20 C21 -174.5(3) . . . . ? C1 C2 C3 C4 2.1(3) . . . . ? C1 C2 C3 C9 179.5(2) . . . . ? C1 C2 C6 C7 -177.6(2) . . . . ? C1 C5 C10 O2 -45.0(3) . . . . ? C1 C5 C10 C11 134.2(2) . . . . ? C2 C1 C5 C4 39.9(2) . . . . ? C2 C1 C5 C10 165.35(19) . . . . ? C2 C3 C4 O1 144.5(2) . . . . ? C2 C3 C4 C5 23.3(2) . . . . ? C2 C3 C9 C8 -2.1(3) . . . . ? C2 C6 C7 C8 -0.4(4) . . . . ? C3 C2 C6 C7 -1.1(4) . . . . ? C3 C4 C5 C1 -38.5(2) . . . . ? C3 C4 C5 C10 -162.3(2) . . . . ? C4 C3 C9 C8 174.8(2) . . . . ? C4 C5 C10 O2 72.5(3) . . . . ? C4 C5 C10 C11 -108.3(2) . . . . ? C5 C1 C2 C3 -26.7(2) . . . . ? C5 C1 C2 C6 150.2(2) . . . . ? C5 C10 C11 C12 -167.3(2) . . . . ? C5 C10 C11 C16 12.3(3) . . . . ? C6 C2 C3 C4 -175.1(2) . . . . ? C6 C2 C3 C9 2.4(3) . . . . ? C6 C7 C8 C9 0.6(4) . . . . ? C7 C8 C9 C3 0.6(4) . . . . ? C9 C3 C4 O1 -32.6(3) . . . . ? C9 C3 C4 C5 -153.8(2) . . . . ? C10 C11 C12 C13 179.4(2) . . . . ? C10 C11 C16 C15 -179.9(2) . . . . ? C11 C12 C13 C14 0.0(4) . . . . ? C12 C11 C16 C15 -0.3(4) . . . . ? C12 C13 C14 C15 0.6(4) . . . . ? C13 C14 C15 C16 -1.0(4) . . . . ? C14 C15 C16 C11 0.9(4) . . . . ? C16 C11 C12 C13 -0.2(4) . . . . ? C20 N1 C1 C2 -116.8(3) . . . . ? C20 N1 C1 C5 127.6(3) . . . . ? C20 C21 C22A C23A 104.3(5) . . . . ? C20 C21 C22 C23 115.2(5) . . . . ? C20 C21 C23 C22 -100.9(5) . . . . ? C20 C21 C23A C22A -110.9(5) . . . . ? C22A C21 C22 C23 4.5(12) . . . . ? C22A C21 C23 C22 -2.7(7) . . . . ? C22 C21 C22A C23A -175.5(15) . . . . ? C22 C21 C23A C22A 1.6(5) . . . . ? C23 C21 C22A C23A -1.9(7) . . . . ? C23 C21 C23A C22A 3.2(12) . . . . ? C23A C21 C22 C23 0.7(5) . . . . ? C23A C21 C23 C22 -178.2(14) . . . . ? data_qian5cult _database_code_depnum_ccdc_archive 'CCDC 902392' #TrackingRef '14114_web_deposit_cif_file_2_JianweiSun_1348151518.qian5cult.cif' _audit_creation_date 2012-09-12 _audit_creation_method ; Olex2 1.2-beta (compiled May 9 2012 12:37:22, GUI svn.r4230) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C20 H23 N O3 S' _chemical_formula_sum 'C20 H23 N O3 S' _chemical_formula_weight 357.45 _chemical_absolute_configuration ad _chemical_melting_point ? 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 Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) _space_group_IT_number 19 _space_group_name_Hall 'P 2ac 2ab' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, -y, z+1/2' 3 'x+1/2, -y+1/2, -z' 4 '-x, y+1/2, -z+1/2' _cell_length_a 5.687 _cell_length_b 10.66360(10) _cell_length_c 29.8209(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1808.42(2) _cell_formula_units_Z 4 _cell_measurement_reflns_used 9561 _cell_measurement_temperature 173.00(14) _cell_measurement_theta_max 71.3734 _cell_measurement_theta_min 4.1423 _exptl_absorpt_coefficient_mu 1.740 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.86309 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.313 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 760 _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.10 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0206 _diffrn_reflns_av_unetI/netI 0.0196 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_number 9437 _diffrn_reflns_theta_full 66.50 _diffrn_reflns_theta_max 66.93 _diffrn_reflns_theta_min 4.40 _diffrn_ambient_temperature 173.00(14) _diffrn_detector_area_resol_mean 15.9578 _diffrn_measured_fraction_theta_full 0.9909 _diffrn_measured_fraction_theta_max 0.9909 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega 38.00 66.00 0.8000 15.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -25.0000 -60.0000 35 #__ type_ start__ end____ width___ exp.time_ 2 omega 41.00 74.60 0.8000 1.0000 omega____ theta____ kappa____ phi______ frames - 0.0000 -178.0000 90.0000 42 #__ type_ start__ end____ width___ exp.time_ 3 omega 38.00 122.00 0.8000 5.0000 omega____ theta____ kappa____ phi______ frames - 55.0000 57.0000 30.0000 105 #__ type_ start__ end____ width___ exp.time_ 4 omega 34.00 82.00 0.8000 5.0000 omega____ theta____ kappa____ phi______ frames - 55.0000 -77.0000 30.0000 60 #__ type_ start__ end____ width___ exp.time_ 5 omega 78.00 123.60 0.8000 5.0000 omega____ theta____ kappa____ phi______ frames - 55.0000 57.0000 -60.0000 57 #__ type_ start__ end____ width___ exp.time_ 6 omega -14.00 18.80 0.8000 5.0000 omega____ theta____ kappa____ phi______ frames - 55.0000 -57.0000 150.0000 41 #__ type_ start__ end____ width___ exp.time_ 7 omega -14.00 79.60 0.8000 5.0000 omega____ theta____ kappa____ phi______ frames - 55.0000 -77.0000 -90.0000 117 #__ type_ start__ end____ width___ exp.time_ 8 omega -47.00 5.00 0.8000 15.0000 omega____ theta____ kappa____ phi______ frames - -64.0000 25.0000 150.0000 65 #__ type_ start__ end____ width___ exp.time_ 9 omega 101.00 147.40 0.8000 15.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -92.0000 0.0000 58 #__ type_ start__ end____ width___ exp.time_ 10 omega 38.00 70.00 0.8000 15.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -38.0000 -150.0000 40 #__ type_ start__ end____ width___ exp.time_ 11 omega 126.00 166.00 0.8000 15.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 64.0000 120.0000 50 #__ type_ start__ end____ width___ exp.time_ 12 omega 42.00 69.20 0.8000 15.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -38.0000 0.0000 34 #__ type_ start__ end____ width___ exp.time_ 13 omega 39.00 84.60 0.8000 15.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -92.0000 0.0000 57 #__ type_ start__ end____ width___ exp.time_ 14 omega 40.00 65.60 0.8000 15.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -38.0000 -90.0000 32 #__ type_ start__ end____ width___ exp.time_ 15 omega 37.00 69.00 0.8000 15.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -25.0000 90.0000 40 #__ type_ start__ end____ width___ exp.time_ 16 omega 44.00 68.80 0.8000 15.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -38.0000 -30.0000 31 #__ type_ start__ end____ width___ exp.time_ 17 omega 41.00 69.80 0.8000 15.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -38.0000 -120.0000 36 #__ type_ start__ end____ width___ exp.time_ 18 omega 39.00 67.00 0.8000 15.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -38.0000 -180.0000 35 #__ type_ start__ end____ width___ exp.time_ 19 omega 37.00 65.00 0.8000 15.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -25.0000 120.0000 35 #__ type_ start__ end____ width___ exp.time_ 20 omega 46.00 142.00 0.8000 15.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -92.0000 150.0000 120 #__ type_ start__ end____ width___ exp.time_ 21 omega 52.00 144.00 0.8000 15.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -92.0000 -60.0000 115 #__ type_ start__ end____ width___ exp.time_ 22 omega 87.00 119.00 0.8000 15.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 64.0000 120.0000 40 #__ type_ start__ end____ width___ exp.time_ 23 omega 48.00 81.60 0.8000 15.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -50.0000 30.0000 42 #__ type_ start__ end____ width___ exp.time_ 24 omega 38.00 70.00 0.8000 15.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -38.0000 150.0000 40 #__ type_ start__ end____ width___ exp.time_ 25 omega 48.00 172.00 0.8000 15.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 0.0000 -60.0000 155 ; _diffrn_measurement_device 'kappa diffractometer' _diffrn_measurement_device_type 'Xcalibur, Sapphire3, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.2182176000 _diffrn_orient_matrix_UB_12 -0.0610783000 _diffrn_orient_matrix_UB_13 -0.0214651000 _diffrn_orient_matrix_UB_21 -0.0196599000 _diffrn_orient_matrix_UB_22 -0.1106800000 _diffrn_orient_matrix_UB_23 0.0329818000 _diffrn_orient_matrix_UB_31 -0.1593801000 _diffrn_orient_matrix_UB_32 -0.0699656000 _diffrn_orient_matrix_UB_33 -0.0334496000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.5418 _diffrn_source 'sealed X-ray tube' _diffrn_source_current 35 _diffrn_source_power 1.75 _diffrn_source_target Cu _diffrn_source_voltage 50 _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 3166 _reflns_number_total 3171 _reflns_odcompleteness_completeness 99.09 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 68.13 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; XL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; XS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 0.185 _refine_diff_density_min -0.187 _refine_diff_density_rms 0.036 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.001(12) _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 229 _refine_ls_number_reflns 3171 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0255 _refine_ls_R_factor_gt 0.0254 _refine_ls_restrained_S_all 1.006 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0489P)^2^+0.2368P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0682 _refine_ls_wR_factor_ref 0.0682 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.23666(6) 0.62457(3) 0.184326(10) 0.02767(10) Uani 1 1 d . . . O1 O 0.28667(19) 0.27663(9) 0.01435(3) 0.0317(2) Uani 1 1 d . . . H1 H 0.1672 0.2401 0.0033 0.038 Uiso 1 1 d R . . O2 O -0.21843(18) 0.38715(9) 0.10727(4) 0.0391(2) Uani 1 1 d . . . O3 O 0.3732(3) 0.74217(9) 0.17791(4) 0.0430(3) Uani 1 1 d . . . N1 N 0.3241(2) 0.51099(10) 0.14984(3) 0.0247(2) Uani 1 1 d . . . H1A H 0.4732 0.5216 0.1470 0.030 Uiso 1 1 d R . . C1 C 0.2309(2) 0.51402(11) 0.10395(4) 0.0229(2) Uani 1 1 d . . . H1B H 0.0804 0.5626 0.1033 0.027 Uiso 1 1 calc R . . C2 C 0.3981(2) 0.56542(11) 0.06903(4) 0.0238(3) Uani 1 1 d . . . C3 C 0.3923(2) 0.49249(11) 0.03046(4) 0.0232(3) Uani 1 1 d . . . C4 C 0.2104(2) 0.39021(11) 0.03505(4) 0.0238(3) Uani 1 1 d . . . H4 H 0.0579 0.4181 0.0217 0.029 Uiso 1 1 calc R . . C5 C 0.1870(2) 0.37928(11) 0.08699(4) 0.0217(2) Uani 1 1 d . . . H5 H 0.3175 0.3248 0.0982 0.026 Uiso 1 1 calc R . . C6 C 0.5557(3) 0.66372(12) 0.07317(5) 0.0288(3) Uani 1 1 d . . . H6 H 0.5586 0.7138 0.0995 0.035 Uiso 1 1 calc R . . C7 C 0.7096(3) 0.68757(12) 0.03803(5) 0.0332(3) Uani 1 1 d . . . H7 H 0.8191 0.7545 0.0403 0.040 Uiso 1 1 calc R . . C8 C 0.7046(2) 0.61430(13) -0.00049(5) 0.0314(3) Uani 1 1 d . . . H8 H 0.8118 0.6312 -0.0242 0.038 Uiso 1 1 calc R . . C9 C 0.5439(3) 0.51605(13) -0.00478(4) 0.0274(3) Uani 1 1 d . . . H9 H 0.5388 0.4666 -0.0313 0.033 Uiso 1 1 calc R . . C10 C -0.0438(2) 0.32254(12) 0.10219(4) 0.0243(3) Uani 1 1 d . . . C11 C -0.0575(2) 0.18450(12) 0.10985(4) 0.0229(3) Uani 1 1 d . . . C12 C 0.1260(2) 0.11839(13) 0.12983(4) 0.0263(3) Uani 1 1 d . . . H12 H 0.2683 0.1602 0.1372 0.032 Uiso 1 1 calc R . . C13 C 0.1010(3) -0.00912(13) 0.13898(5) 0.0316(3) Uani 1 1 d . . . H13 H 0.2249 -0.0537 0.1532 0.038 Uiso 1 1 calc R . . C14 C -0.1040(3) -0.07082(13) 0.12735(5) 0.0338(3) Uani 1 1 d . . . H14 H -0.1203 -0.1578 0.1335 0.041 Uiso 1 1 calc R . . C15 C -0.2863(3) -0.00606(13) 0.10672(5) 0.0329(3) Uani 1 1 d . . . H15 H -0.4260 -0.0490 0.0984 0.039 Uiso 1 1 calc R . . C16 C -0.2643(2) 0.12124(12) 0.09829(4) 0.0268(3) Uani 1 1 d . . . H16 H -0.3901 0.1657 0.0846 0.032 Uiso 1 1 calc R . . C21 C 0.3500(3) 0.55517(13) 0.23683(4) 0.0285(3) Uani 1 1 d . . . C22 C 0.6175(3) 0.54560(18) 0.23431(5) 0.0410(4) Uani 1 1 d . . . H22A H 0.6613 0.4776 0.2139 0.062 Uiso 1 1 calc R . . H22B H 0.6807 0.5282 0.2642 0.062 Uiso 1 1 calc R . . H22C H 0.6822 0.6249 0.2232 0.062 Uiso 1 1 calc R . . C23 C 0.2768(3) 0.65008(15) 0.27290(5) 0.0398(3) Uani 1 1 d . . . H23A H 0.3535 0.7307 0.2670 0.060 Uiso 1 1 calc R . . H23B H 0.3245 0.6191 0.3025 0.060 Uiso 1 1 calc R . . H23C H 0.1058 0.6610 0.2722 0.060 Uiso 1 1 calc R . . C24 C 0.2350(3) 0.42857(14) 0.24484(5) 0.0366(3) Uani 1 1 d . . . H24A H 0.0637 0.4387 0.2455 0.055 Uiso 1 1 calc R . . H24B H 0.2886 0.3945 0.2736 0.055 Uiso 1 1 calc R . . H24C H 0.2784 0.3709 0.2206 0.055 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 0.03105(17) 0.02553(16) 0.02642(16) -0.00303(11) -0.00263(13) 0.00677(14) O1 0.0359(5) 0.0245(4) 0.0348(5) -0.0083(4) 0.0036(4) -0.0048(4) O2 0.0237(5) 0.0292(5) 0.0643(7) 0.0043(5) 0.0046(5) 0.0043(4) O3 0.0684(8) 0.0238(5) 0.0369(5) -0.0008(4) -0.0025(5) -0.0008(5) N1 0.0233(6) 0.0253(5) 0.0255(5) -0.0019(4) -0.0010(4) 0.0045(4) C1 0.0231(6) 0.0191(5) 0.0264(5) -0.0003(4) -0.0029(5) 0.0007(5) C2 0.0253(6) 0.0186(6) 0.0275(6) 0.0030(5) -0.0039(5) 0.0036(5) C3 0.0247(7) 0.0186(5) 0.0262(6) 0.0039(5) -0.0038(5) 0.0016(5) C4 0.0240(6) 0.0216(6) 0.0256(6) -0.0015(5) -0.0023(5) 0.0000(5) C5 0.0201(6) 0.0190(5) 0.0261(6) 0.0013(5) -0.0015(5) 0.0006(5) C6 0.0342(8) 0.0198(6) 0.0325(7) 0.0015(5) -0.0024(6) -0.0032(5) C7 0.0324(7) 0.0236(6) 0.0436(8) 0.0053(5) -0.0014(6) -0.0055(6) C8 0.0306(7) 0.0286(6) 0.0351(7) 0.0103(5) 0.0032(6) -0.0011(6) C9 0.0300(7) 0.0262(6) 0.0262(6) 0.0035(5) -0.0021(5) 0.0014(5) C10 0.0209(6) 0.0242(6) 0.0277(6) 0.0002(5) -0.0009(5) 0.0015(5) C11 0.0235(6) 0.0255(6) 0.0198(5) 0.0004(5) 0.0047(5) -0.0005(5) C12 0.0237(6) 0.0262(6) 0.0289(6) 0.0024(5) 0.0016(5) -0.0008(6) C13 0.0346(8) 0.0273(7) 0.0329(7) 0.0057(5) 0.0034(6) 0.0037(6) C14 0.0424(9) 0.0215(6) 0.0375(7) 0.0005(5) 0.0083(7) -0.0029(6) C15 0.0307(8) 0.0299(7) 0.0382(7) -0.0057(6) 0.0047(6) -0.0087(6) C16 0.0233(6) 0.0295(6) 0.0277(6) -0.0023(5) 0.0020(5) 0.0014(6) C21 0.0263(7) 0.0345(7) 0.0247(6) 0.0007(5) -0.0010(5) 0.0016(6) C22 0.0267(7) 0.0619(11) 0.0343(7) 0.0012(7) -0.0046(6) 0.0021(8) C23 0.0457(9) 0.0443(8) 0.0294(7) -0.0070(6) 0.0026(7) -0.0038(7) C24 0.0373(8) 0.0348(7) 0.0376(7) 0.0051(6) 0.0014(7) 0.0012(7) _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 O3 1.4872(12) . ? S1 N1 1.6649(11) . ? S1 C21 1.8479(14) . ? O1 C4 1.4269(16) . ? O2 C10 1.2182(17) . ? N1 C1 1.4679(16) . ? C1 C2 1.5132(18) . ? C1 C5 1.5435(16) . ? C2 C3 1.3889(18) . ? C2 C6 1.3847(19) . ? C3 C4 1.5092(17) . ? C3 C9 1.3821(19) . ? C4 C5 1.5590(16) . ? C5 C10 1.5146(17) . ? C6 C7 1.389(2) . ? C7 C8 1.389(2) . ? C8 C9 1.396(2) . ? C10 C11 1.4916(18) . ? C11 C12 1.3930(19) . ? C11 C16 1.3990(19) . ? C12 C13 1.394(2) . ? C13 C14 1.383(2) . ? C14 C15 1.389(2) . ? C15 C16 1.3862(19) . ? C21 C22 1.526(2) . ? C21 C23 1.535(2) . ? C21 C24 1.519(2) . ? 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 O3 S1 N1 112.21(6) . . ? O3 S1 C21 105.34(7) . . ? N1 S1 C21 97.35(6) . . ? C1 N1 S1 116.87(8) . . ? N1 C1 C2 114.98(11) . . ? N1 C1 C5 110.08(10) . . ? C2 C1 C5 102.32(10) . . ? C3 C2 C1 110.61(11) . . ? C6 C2 C1 128.30(12) . . ? C6 C2 C3 120.88(12) . . ? C2 C3 C4 110.24(11) . . ? C9 C3 C2 120.86(12) . . ? C9 C3 C4 128.87(12) . . ? O1 C4 C3 111.47(11) . . ? O1 C4 C5 113.10(10) . . ? C3 C4 C5 101.70(10) . . ? C1 C5 C4 104.01(10) . . ? C10 C5 C1 114.45(11) . . ? C10 C5 C4 113.66(10) . . ? C2 C6 C7 118.63(13) . . ? C6 C7 C8 120.54(13) . . ? C7 C8 C9 120.72(13) . . ? C3 C9 C8 118.36(12) . . ? O2 C10 C5 121.18(11) . . ? O2 C10 C11 119.77(12) . . ? C11 C10 C5 119.03(11) . . ? C12 C11 C10 121.73(12) . . ? C12 C11 C16 119.41(12) . . ? C16 C11 C10 118.81(12) . . ? C11 C12 C13 120.06(14) . . ? C14 C13 C12 120.06(14) . . ? C13 C14 C15 120.24(13) . . ? C16 C15 C14 119.98(14) . . ? C15 C16 C11 120.22(13) . . ? C22 C21 S1 109.44(10) . . ? C22 C21 C23 110.42(13) . . ? C23 C21 S1 103.60(10) . . ? C24 C21 S1 109.81(10) . . ? C24 C21 C22 112.19(13) . . ? C24 C21 C23 111.04(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 O1 H1 O1 0.85 2.23 3.0232(6) 154.4 3_455 N1 H1A O2 0.86 2.56 3.1818(15) 130.5 1_655 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 S1 N1 C1 C2 101.30(11) . . . . ? S1 N1 C1 C5 -143.81(9) . . . . ? O1 C4 C5 C1 151.98(10) . . . . ? O1 C4 C5 C10 -82.92(13) . . . . ? O2 C10 C11 C12 -142.10(14) . . . . ? O2 C10 C11 C16 35.23(19) . . . . ? O3 S1 N1 C1 -81.58(11) . . . . ? O3 S1 C21 C22 -52.13(12) . . . . ? O3 S1 C21 C23 65.65(11) . . . . ? O3 S1 C21 C24 -175.69(10) . . . . ? N1 S1 C21 C22 63.37(12) . . . . ? N1 S1 C21 C23 -178.85(10) . . . . ? N1 S1 C21 C24 -60.18(11) . . . . ? N1 C1 C2 C3 136.93(11) . . . . ? N1 C1 C2 C6 -37.80(18) . . . . ? N1 C1 C5 C4 -153.26(10) . . . . ? N1 C1 C5 C10 82.14(13) . . . . ? C1 C2 C3 C4 3.28(14) . . . . ? C1 C2 C3 C9 -175.10(12) . . . . ? C1 C2 C6 C7 173.80(13) . . . . ? C1 C5 C10 O2 33.46(17) . . . . ? C1 C5 C10 C11 -148.13(12) . . . . ? C2 C1 C5 C4 -30.57(12) . . . . ? C2 C1 C5 C10 -155.17(10) . . . . ? C2 C3 C4 O1 -143.26(11) . . . . ? C2 C3 C4 C5 -22.46(13) . . . . ? C2 C3 C9 C8 0.59(19) . . . . ? C2 C6 C7 C8 0.1(2) . . . . ? C3 C2 C6 C7 -0.5(2) . . . . ? C3 C4 C5 C1 32.33(12) . . . . ? C3 C4 C5 C10 157.43(10) . . . . ? C4 C3 C9 C8 -177.45(12) . . . . ? C4 C5 C10 O2 -85.85(16) . . . . ? C4 C5 C10 C11 92.56(13) . . . . ? C5 C1 C2 C3 17.62(13) . . . . ? C5 C1 C2 C6 -157.11(13) . . . . ? C5 C10 C11 C12 39.47(18) . . . . ? C5 C10 C11 C16 -143.20(12) . . . . ? C6 C2 C3 C4 178.46(12) . . . . ? C6 C2 C3 C9 0.08(19) . . . . ? C6 C7 C8 C9 0.5(2) . . . . ? C7 C8 C9 C3 -0.9(2) . . . . ? C9 C3 C4 O1 34.95(18) . . . . ? C9 C3 C4 C5 155.75(13) . . . . ? C10 C11 C12 C13 176.00(12) . . . . ? C10 C11 C16 C15 -177.29(12) . . . . ? C11 C12 C13 C14 1.4(2) . . . . ? C12 C11 C16 C15 0.10(19) . . . . ? C12 C13 C14 C15 -0.3(2) . . . . ? C13 C14 C15 C16 -0.9(2) . . . . ? C14 C15 C16 C11 1.0(2) . . . . ? C16 C11 C12 C13 -1.31(19) . . . . ? C21 S1 N1 C1 168.49(10) . . . . ? data_qian6cult _database_code_depnum_ccdc_archive 'CCDC 904189' #TrackingRef '14408_web_deposit_cif_file_0_JianweiSun_1349268834.qian6cult.cif' _audit_creation_date 2012-09-28 _audit_creation_method ; Olex2 1.2-beta (compiled May 9 2012 12:37:22, GUI svn.r4230) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C11 H10 N2 O2 S' _chemical_formula_sum 'C11 H10 N2 O2 S' _chemical_formula_weight 234.27 _chemical_melting_point ? 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 P2(1)/n _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x-1/2, -y-1/2, z-1/2' _cell_length_a 14.0959(6) _cell_length_b 7.5933(3) _cell_length_c 20.2857(8) _cell_angle_alpha 90.00 _cell_angle_beta 104.158(4) _cell_angle_gamma 90.00 _cell_volume 2105.31(15) _cell_formula_units_Z 8 _cell_measurement_reflns_used 3712 _cell_measurement_temperature 173.00(14) _cell_measurement_theta_max 71.5126 _cell_measurement_theta_min 9.7490 _exptl_absorpt_coefficient_mu 2.629 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.45580 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.478 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 976 _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.25 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0247 _diffrn_reflns_av_unetI/netI 0.0275 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_number 7985 _diffrn_reflns_theta_full 66.50 _diffrn_reflns_theta_max 66.98 _diffrn_reflns_theta_min 10.04 _diffrn_ambient_temperature 173.00(14) _diffrn_detector_area_resol_mean 15.9578 _diffrn_measured_fraction_theta_full 0.954 _diffrn_measured_fraction_theta_max 0.954 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega 46.00 83.00 1.0000 8.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -50.0000 90.0000 37 #__ type_ start__ end____ width___ exp.time_ 2 omega 79.00 118.00 1.0000 4.0000 omega____ theta____ kappa____ phi______ frames - 55.0000 125.0000 -60.0000 39 #__ type_ start__ end____ width___ exp.time_ 3 omega 73.00 122.00 1.0000 4.0000 omega____ theta____ kappa____ phi______ frames - 55.0000 125.0000 0.0000 49 #__ type_ start__ end____ width___ exp.time_ 4 omega 36.00 123.00 1.0000 4.0000 omega____ theta____ kappa____ phi______ frames - 55.0000 57.0000 0.0000 87 #__ type_ start__ end____ width___ exp.time_ 5 omega -17.00 71.00 1.0000 4.0000 omega____ theta____ kappa____ phi______ frames - 55.0000 -38.0000 30.0000 88 #__ type_ start__ end____ width___ exp.time_ 6 omega 141.00 168.00 1.0000 8.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 12.0000 -180.0000 27 #__ type_ start__ end____ width___ exp.time_ 7 omega 89.00 162.00 1.0000 8.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 50.0000 -120.0000 73 #__ type_ start__ end____ width___ exp.time_ 8 omega 84.00 157.00 1.0000 8.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 38.0000 30.0000 73 #__ type_ start__ end____ width___ exp.time_ 9 omega 45.00 87.00 1.0000 8.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -111.0000 60.0000 42 #__ type_ start__ end____ width___ exp.time_ 10 omega 40.00 71.00 1.0000 8.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -25.0000 -120.0000 31 #__ type_ start__ end____ width___ exp.time_ 11 omega 39.00 65.00 1.0000 8.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -48.0000 -63.0000 26 #__ type_ start__ end____ width___ exp.time_ 12 omega 64.00 102.00 1.0000 8.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 12.0000 -180.0000 38 #__ type_ start__ end____ width___ exp.time_ 13 omega 41.00 86.00 1.0000 8.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -111.0000 -30.0000 45 #__ type_ start__ end____ width___ exp.time_ 14 omega 44.00 140.00 1.0000 8.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -77.0000 90.0000 96 #__ type_ start__ end____ width___ exp.time_ 15 omega 34.00 112.00 1.0000 4.0000 omega____ theta____ kappa____ phi______ frames - 55.0000 57.0000 90.0000 78 #__ type_ start__ end____ width___ exp.time_ 16 omega 25.00 125.00 1.0000 4.0000 omega____ theta____ kappa____ phi______ frames - 55.0000 77.0000 150.0000 100 ; _diffrn_measurement_device 'kappa diffractometer' _diffrn_measurement_device_type 'Xcalibur, Sapphire3, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0108717000 _diffrn_orient_matrix_UB_12 -0.1174984000 _diffrn_orient_matrix_UB_13 0.0633656000 _diffrn_orient_matrix_UB_21 -0.1120860000 _diffrn_orient_matrix_UB_22 -0.0214332000 _diffrn_orient_matrix_UB_23 -0.0156327000 _diffrn_orient_matrix_UB_31 0.0066378000 _diffrn_orient_matrix_UB_32 -0.1646828000 _diffrn_orient_matrix_UB_33 -0.0432290000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.5418 _diffrn_source 'sealed X-ray tube' _diffrn_source_current 35 _diffrn_source_power 1.75 _diffrn_source_target Cu _diffrn_source_voltage 50 _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 3336 _reflns_number_total 3575 _reflns_odcompleteness_completeness 98.46 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 68.13 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; XL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _refine_diff_density_max 0.579 _refine_diff_density_min -0.393 _refine_diff_density_rms 0.062 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.005 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 291 _refine_ls_number_reflns 3575 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0616 _refine_ls_R_factor_gt 0.0588 _refine_ls_restrained_S_all 1.005 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0961P)^2^+1.7503P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1546 _refine_ls_wR_factor_ref 0.1573 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.93052(5) 0.17509(11) 0.56623(3) 0.0450(2) Uani 1 1 d . . . O1 O 0.89599(16) 0.1115(3) 0.39970(10) 0.0480(5) Uani 1 1 d . . . H1 H 0.9439 0.0972 0.4332 0.072 Uiso 1 1 calc R . . O2 O 0.59274(16) 0.0800(3) 0.57815(10) 0.0505(5) Uani 1 1 d . . . N1 N 0.77541(17) 0.1799(3) 0.46069(11) 0.0389(5) Uani 1 1 d . . . C2 C 0.8118(2) 0.1574(4) 0.52729(13) 0.0384(6) Uani 1 1 d . . . N3 N 0.74472(19) 0.1161(3) 0.56388(11) 0.0423(6) Uani 1 1 d . . . H3 H 0.7684 0.0824 0.6062 0.051 Uiso 1 1 calc R . . C4 C 0.6442(2) 0.1220(4) 0.54126(13) 0.0421(6) Uani 1 1 d . . . C5 C 0.6058(2) 0.1883(4) 0.46960(14) 0.0431(6) Uani 1 1 d . . . H5A H 0.5400 0.1383 0.4503 0.052 Uiso 1 1 calc R . . H5B H 0.5997 0.3181 0.4701 0.052 Uiso 1 1 calc R . . C6 C 0.6734(2) 0.1370(4) 0.42585(13) 0.0411(6) Uani 1 1 d . . . H6 H 0.6680 0.0073 0.4172 0.049 Uiso 1 1 calc R . . C7 C 0.6644(2) 0.2318(4) 0.35896(13) 0.0406(6) Uani 1 1 d . . . C8 C 0.5809(2) 0.2579(5) 0.30748(15) 0.0504(7) Uani 1 1 d . . . H8 H 0.5185 0.2216 0.3124 0.060 Uiso 1 1 calc R . . C9 C 0.5916(3) 0.3394(5) 0.24795(16) 0.0584(9) Uani 1 1 d . . . H9 H 0.5356 0.3591 0.2117 0.070 Uiso 1 1 calc R . . C10 C 0.6823(3) 0.3916(5) 0.24127(16) 0.0615(9) Uani 1 1 d . . . H10 H 0.6877 0.4461 0.2002 0.074 Uiso 1 1 calc R . . C11 C 0.7662(3) 0.3664(5) 0.29324(16) 0.0551(8) Uani 1 1 d . . . H11 H 0.8287 0.4034 0.2887 0.066 Uiso 1 1 calc R . . C12 C 0.7545(2) 0.2844(4) 0.35243(13) 0.0405(6) Uani 1 1 d . . . C13 C 0.8344(2) 0.2425(4) 0.41480(13) 0.0394(6) Uani 1 1 d . . . H13 H 0.8722 0.3505 0.4332 0.047 Uiso 1 1 calc R . . S1A S 0.32411(5) 0.38369(11) 0.23272(3) 0.0474(2) Uani 1 1 d . . . O1A O 0.38717(17) 0.5239(3) 0.38962(11) 0.0556(6) Uani 1 1 d . . . H1A H 0.4089 0.5314 0.3547 0.083 Uiso 1 1 calc R . . O2A O -0.02485(17) 0.3056(4) 0.20929(12) 0.0716(8) Uani 1 1 d . . . N1A N 0.23478(18) 0.3878(3) 0.33362(11) 0.0422(5) Uani 1 1 d . . . C2A C 0.2270(2) 0.3821(4) 0.26652(14) 0.0414(6) Uani 1 1 d . . . N3A N 0.13401(19) 0.3756(3) 0.22643(11) 0.0419(5) Uani 1 1 d . . . H3A H 0.1258 0.4045 0.1834 0.050 Uiso 1 1 calc R . . C4A C 0.0503(3) 0.3267(5) 0.24780(15) 0.0525(8) Uani 1 1 d . . . C5A C 0.0672(2) 0.2933(5) 0.32299(15) 0.0547(8) Uani 1 1 d . . . H5AA H 0.0066 0.3187 0.3377 0.066 Uiso 1 1 calc R . . H5AB H 0.0844 0.1680 0.3329 0.066 Uiso 1 1 calc R . . C6A C 0.1485(2) 0.4084(4) 0.36122(15) 0.0471(7) Uani 1 1 d . . . H6A H 0.1268 0.5342 0.3572 0.056 Uiso 1 1 calc R . . C7A C 0.1918(3) 0.3633(4) 0.43599(14) 0.0471(7) Uani 1 1 d . . . C8A C 0.1438(3) 0.3432(5) 0.48798(16) 0.0531(8) Uani 1 1 d . . . H8A H 0.0744 0.3468 0.4791 0.064 Uiso 1 1 calc R . . C9A C 0.2016(3) 0.3175(4) 0.55355(15) 0.0517(8) Uani 1 1 d . . . H9A H 0.1709 0.3002 0.5899 0.062 Uiso 1 1 calc R . . C10A C 0.3018(3) 0.3168(4) 0.56685(15) 0.0562(9) Uani 1 1 d . . . H10A H 0.3391 0.3062 0.6125 0.067 Uiso 1 1 calc R . . C11A C 0.3498(3) 0.3312(4) 0.51452(15) 0.0500(7) Uani 1 1 d . . . H11A H 0.4191 0.3262 0.5233 0.060 Uiso 1 1 calc R . . C12A C 0.2916(2) 0.3534(4) 0.44874(14) 0.0437(7) Uani 1 1 d . . . C13A C 0.3280(2) 0.3719(4) 0.38517(14) 0.0429(6) Uani 1 1 d . . . H13A H 0.3645 0.2643 0.3772 0.051 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 0.0427(4) 0.0625(5) 0.0265(3) -0.0030(3) 0.0024(3) 0.0102(3) O1 0.0486(11) 0.0635(13) 0.0300(9) -0.0014(9) 0.0059(8) 0.0170(10) O2 0.0477(11) 0.0663(14) 0.0385(10) -0.0123(9) 0.0126(9) -0.0151(10) N1 0.0398(12) 0.0506(13) 0.0246(10) 0.0022(9) 0.0046(9) 0.0048(10) C2 0.0494(15) 0.0398(14) 0.0253(12) 0.0002(10) 0.0078(11) 0.0068(11) N3 0.0525(14) 0.0516(14) 0.0211(10) 0.0038(9) 0.0060(9) 0.0045(11) C4 0.0550(17) 0.0413(15) 0.0289(13) -0.0031(11) 0.0082(12) -0.0087(12) C5 0.0410(15) 0.0539(17) 0.0332(14) 0.0019(12) 0.0066(11) -0.0046(12) C6 0.0460(15) 0.0455(15) 0.0300(13) 0.0012(11) 0.0059(11) 0.0025(12) C7 0.0501(16) 0.0447(15) 0.0262(12) 0.0006(11) 0.0081(11) 0.0076(12) C8 0.0468(16) 0.067(2) 0.0341(14) 0.0004(13) 0.0032(12) 0.0057(14) C9 0.060(2) 0.077(2) 0.0312(14) 0.0073(14) -0.0028(13) 0.0151(17) C10 0.071(2) 0.081(2) 0.0298(14) 0.0177(15) 0.0089(14) 0.0135(18) C11 0.0565(19) 0.071(2) 0.0380(16) 0.0112(14) 0.0123(14) 0.0038(15) C12 0.0460(15) 0.0472(15) 0.0259(12) -0.0009(11) 0.0043(11) 0.0099(12) C13 0.0436(14) 0.0499(15) 0.0248(12) 0.0000(11) 0.0084(10) 0.0050(12) S1A 0.0447(4) 0.0649(5) 0.0334(4) 0.0010(3) 0.0107(3) -0.0032(3) O1A 0.0598(13) 0.0616(14) 0.0424(11) -0.0021(10) 0.0068(10) -0.0131(11) O2A 0.0401(12) 0.127(2) 0.0473(13) -0.0089(14) 0.0105(10) -0.0226(13) N1A 0.0424(13) 0.0537(14) 0.0295(11) 0.0016(10) 0.0068(9) -0.0010(10) C2A 0.0549(17) 0.0379(14) 0.0295(13) -0.0009(10) 0.0067(12) 0.0004(12) N3A 0.0511(14) 0.0503(13) 0.0228(10) 0.0000(9) 0.0063(9) 0.0012(10) C4A 0.058(2) 0.067(2) 0.0336(15) 0.0023(13) 0.0149(14) 0.0004(15) C5A 0.0462(17) 0.085(2) 0.0336(15) -0.0001(15) 0.0112(12) -0.0027(16) C6A 0.0472(16) 0.0541(17) 0.0414(15) 0.0051(13) 0.0138(12) 0.0069(13) C7A 0.066(2) 0.0445(15) 0.0285(13) -0.0068(11) 0.0073(13) 0.0063(13) C8A 0.0581(19) 0.061(2) 0.0412(16) -0.0087(14) 0.0152(14) 0.0003(15) C9A 0.081(2) 0.0462(16) 0.0312(14) 0.0013(12) 0.0206(15) 0.0015(15) C10A 0.085(3) 0.0460(17) 0.0293(14) -0.0016(12) -0.0017(14) 0.0093(16) C11A 0.0605(19) 0.0483(17) 0.0371(15) -0.0026(12) 0.0041(14) 0.0020(14) C12A 0.0611(18) 0.0381(14) 0.0312(13) -0.0026(11) 0.0101(12) -0.0014(12) C13A 0.0450(15) 0.0481(16) 0.0321(13) -0.0013(11) 0.0030(11) 0.0012(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 S1 C2 1.672(3) . ? O1 C13 1.403(3) . ? O2 C4 1.205(4) . ? N1 C2 1.334(3) . ? N1 C6 1.475(4) . ? N1 C13 1.470(4) . ? C2 N3 1.374(4) . ? N3 C4 1.379(4) . ? C4 C5 1.508(4) . ? C5 C6 1.504(4) . ? C6 C7 1.514(4) . ? C7 C8 1.383(4) . ? C7 C12 1.368(4) . ? C8 C9 1.398(5) . ? C9 C10 1.376(6) . ? C10 C11 1.392(5) . ? C11 C12 1.398(4) . ? C12 C13 1.508(4) . ? S1A C2A 1.675(3) . ? O1A C13A 1.414(4) . ? O2A C4A 1.163(4) . ? N1A C2A 1.339(4) . ? N1A C6A 1.467(4) . ? N1A C13A 1.470(4) . ? C2A N3A 1.364(4) . ? N3A C4A 1.403(4) . ? C4A C5A 1.507(4) . ? C5A C6A 1.498(5) . ? C6A C7A 1.529(4) . ? C7A C8A 1.394(5) . ? C7A C12A 1.370(5) . ? C8A C9A 1.393(5) . ? C9A C10A 1.371(5) . ? C10A C11A 1.396(5) . ? C11A C12A 1.395(4) . ? C12A C13A 1.506(4) . ? 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 N1 C6 123.1(2) . . ? C2 N1 C13 123.1(2) . . ? C13 N1 C6 113.8(2) . . ? N1 C2 S1 124.1(2) . . ? N1 C2 N3 115.5(3) . . ? N3 C2 S1 120.33(19) . . ? C2 N3 C4 126.9(2) . . ? O2 C4 N3 120.7(3) . . ? O2 C4 C5 123.9(3) . . ? N3 C4 C5 115.4(2) . . ? C6 C5 C4 110.6(2) . . ? N1 C6 C5 110.1(2) . . ? N1 C6 C7 100.5(2) . . ? C5 C6 C7 118.6(2) . . ? C8 C7 C6 127.9(3) . . ? C12 C7 C6 110.4(2) . . ? C12 C7 C8 121.6(3) . . ? C7 C8 C9 117.6(3) . . ? C10 C9 C8 120.8(3) . . ? C9 C10 C11 121.6(3) . . ? C10 C11 C12 117.1(3) . . ? C7 C12 C11 121.4(3) . . ? C7 C12 C13 112.2(2) . . ? C11 C12 C13 126.5(3) . . ? O1 C13 N1 112.7(2) . . ? O1 C13 C12 110.0(2) . . ? N1 C13 C12 100.2(2) . . ? C2A N1A C6A 121.5(2) . . ? C2A N1A C13A 123.9(2) . . ? C6A N1A C13A 114.7(2) . . ? N1A C2A S1A 122.9(2) . . ? N1A C2A N3A 115.8(3) . . ? N3A C2A S1A 121.2(2) . . ? C2A N3A C4A 125.7(2) . . ? O2A C4A N3A 121.7(3) . . ? O2A C4A C5A 123.3(3) . . ? N3A C4A C5A 114.9(3) . . ? C6A C5A C4A 109.7(3) . . ? N1A C6A C5A 109.9(3) . . ? N1A C6A C7A 100.8(2) . . ? C5A C6A C7A 116.9(3) . . ? C8A C7A C6A 128.7(3) . . ? C12A C7A C6A 110.0(3) . . ? C12A C7A C8A 121.2(3) . . ? C9A C8A C7A 117.3(3) . . ? C10A C9A C8A 121.5(3) . . ? C9A C10A C11A 121.2(3) . . ? C12A C11A C10A 117.1(3) . . ? C7A C12A C11A 121.6(3) . . ? C7A C12A C13A 112.5(3) . . ? C11A C12A C13A 125.9(3) . . ? O1A C13A N1A 112.9(2) . . ? O1A C13A C12A 109.9(2) . . ? N1A C13A C12A 100.7(2) . . ? 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 S1 C2 N3 C4 169.8(2) . . . . ? O2 C4 C5 C6 -149.0(3) . . . . ? N1 C2 N3 C4 -10.6(4) . . . . ? N1 C6 C7 C8 -171.5(3) . . . . ? N1 C6 C7 C12 12.1(3) . . . . ? C2 N1 C6 C5 39.2(4) . . . . ? C2 N1 C6 C7 165.2(2) . . . . ? C2 N1 C13 O1 76.1(3) . . . . ? C2 N1 C13 C12 -167.0(3) . . . . ? C2 N3 C4 O2 179.0(3) . . . . ? C2 N3 C4 C5 -2.7(4) . . . . ? N3 C4 C5 C6 32.8(3) . . . . ? C4 C5 C6 N1 -48.1(3) . . . . ? C4 C5 C6 C7 -163.0(3) . . . . ? C5 C6 C7 C8 -51.5(4) . . . . ? C5 C6 C7 C12 132.1(3) . . . . ? C6 N1 C2 S1 170.2(2) . . . . ? C6 N1 C2 N3 -9.4(4) . . . . ? C6 N1 C13 O1 -101.4(3) . . . . ? C6 N1 C13 C12 15.5(3) . . . . ? C6 C7 C8 C9 -175.7(3) . . . . ? C6 C7 C12 C11 176.4(3) . . . . ? C6 C7 C12 C13 -3.4(3) . . . . ? C7 C8 C9 C10 0.0(5) . . . . ? C7 C12 C13 O1 111.9(3) . . . . ? C7 C12 C13 N1 -7.0(3) . . . . ? C8 C7 C12 C11 -0.2(5) . . . . ? C8 C7 C12 C13 180.0(3) . . . . ? C8 C9 C10 C11 -0.4(6) . . . . ? C9 C10 C11 C12 0.5(6) . . . . ? C10 C11 C12 C7 -0.2(5) . . . . ? C10 C11 C12 C13 179.6(3) . . . . ? C11 C12 C13 O1 -67.9(4) . . . . ? C11 C12 C13 N1 173.3(3) . . . . ? C12 C7 C8 C9 0.4(5) . . . . ? C13 N1 C2 S1 -7.0(4) . . . . ? C13 N1 C2 N3 173.4(2) . . . . ? C13 N1 C6 C5 -143.3(2) . . . . ? C13 N1 C6 C7 -17.3(3) . . . . ? S1A C2A N3A C4A 161.8(3) . . . . ? O2A C4A C5A C6A -152.6(4) . . . . ? N1A C2A N3A C4A -18.5(4) . . . . ? N1A C6A C7A C8A -173.4(3) . . . . ? N1A C6A C7A C12A 10.3(3) . . . . ? C2A N1A C6A C5A 43.1(4) . . . . ? C2A N1A C6A C7A 167.1(3) . . . . ? C2A N1A C13A O1A 72.9(3) . . . . ? C2A N1A C13A C12A -170.0(3) . . . . ? C2A N3A C4A O2A -171.4(3) . . . . ? C2A N3A C4A C5A 4.9(5) . . . . ? N3A C4A C5A C6A 31.2(4) . . . . ? C4A C5A C6A N1A -52.2(4) . . . . ? C4A C5A C6A C7A -166.2(3) . . . . ? C5A C6A C7A C8A -54.3(5) . . . . ? C5A C6A C7A C12A 129.4(3) . . . . ? C6A N1A C2A S1A 172.3(2) . . . . ? C6A N1A C2A N3A -7.5(4) . . . . ? C6A N1A C13A O1A -108.0(3) . . . . ? C6A N1A C13A C12A 9.2(3) . . . . ? C6A C7A C8A C9A -174.2(3) . . . . ? C6A C7A C12A C11A 173.6(3) . . . . ? C6A C7A C12A C13A -5.5(4) . . . . ? C7A C8A C9A C10A 1.7(5) . . . . ? C7A C12A C13A O1A 117.5(3) . . . . ? C7A C12A C13A N1A -1.8(3) . . . . ? C8A C7A C12A C11A -3.1(5) . . . . ? C8A C7A C12A C13A 177.8(3) . . . . ? C8A C9A C10A C11A -3.9(5) . . . . ? C9A C10A C11A C12A 2.5(5) . . . . ? C10A C11A C12A C7A 1.0(4) . . . . ? C10A C11A C12A C13A 179.9(3) . . . . ? C11A C12A C13A O1A -61.6(4) . . . . ? C11A C12A C13A N1A 179.1(3) . . . . ? C12A C7A C8A C9A 1.7(5) . . . . ? C13A N1A C2A S1A -8.6(4) . . . . ? C13A N1A C2A N3A 171.6(2) . . . . ? C13A N1A C6A C5A -136.1(3) . . . . ? C13A N1A C6A C7A -12.1(3) . . . . ?