Supplementary Material (ESI) for Chemical Communications This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Jing Wang' _publ_contact_author_email jdbd1214@163.com loop_ _publ_author_name 'Jing Wang' 'Jinjin Wang' 'Yuanxun Zhu' 'Ping Lu' 'Yan-Guang Wang' data_100125_hell0113 _database_code_depnum_ccdc_archive 'CCDC 784633' #TrackingRef 'N-(1-(1,2-dimethyl-1H-indol-3-yl)-2- #oxo-2-phenylethylidene)-4-methylbenzenesulfonamide.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C25 H22 N2 O3 S' _chemical_formula_sum 'C25 H22 N2 O3 S' _chemical_formula_weight 430.51 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' 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' 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' _symmetry_space_group_name_Hall '-P 2ybc' 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 7.3334(3) _cell_length_b 17.1511(6) _cell_length_c 17.5542(7) _cell_angle_alpha 90.00 _cell_angle_beta 101.515(4) _cell_angle_gamma 90.00 _cell_volume 2163.46(14) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3843 _cell_measurement_theta_min 2.5735 _cell_measurement_theta_max 66.9440 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.322 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 904 _exptl_absorpt_coefficient_mu 1.570 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.89 _exptl_absorpt_correction_T_max 0.91 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.53 (release 17-11-2009 CrysAlis171 .NET) (compiled Nov 17 2009,16:58:22) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.3592 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14958 _diffrn_reflns_av_R_equivalents 0.0515 _diffrn_reflns_av_sigmaI/netI 0.0365 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.64 _diffrn_reflns_theta_max 67.14 _reflns_number_total 3708 _reflns_number_gt 2441 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) ; _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) ; _computing_molecular_graphics ; OLEX2: a complete structure solution, refinement and analysis program. Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341 ; _computing_publication_material ; OLEX2: a complete structure solution, refinement and analysis program. Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341 ; _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^)+(0.0612P)^2^+0.0871P] 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 3708 _refine_ls_number_parameters 283 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0742 _refine_ls_R_factor_gt 0.0431 _refine_ls_wR_factor_ref 0.1206 _refine_ls_wR_factor_gt 0.1058 _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_restrained_S_all 1.020 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 1.00530(9) 0.31015(4) 0.45835(4) 0.0743(2) Uani 1 1 d . . . O1 O 0.9773(2) 0.16175(12) 0.32306(11) 0.0821(5) Uani 1 1 d . . . O2 O 0.9279(3) 0.32759(11) 0.37902(10) 0.0880(5) Uani 1 1 d . . . O3 O 1.2037(3) 0.31208(13) 0.48178(13) 0.0950(6) Uani 1 1 d . . . N1 N 0.7318(2) -0.02457(10) 0.48579(12) 0.0625(5) Uani 1 1 d . . . N2 N 0.9348(3) 0.22671(11) 0.48677(11) 0.0704(5) Uani 1 1 d . . . C1 C 0.8303(3) 0.13525(16) 0.61793(14) 0.0701(6) Uani 1 1 d . . . H1 H 0.8642 0.1873 0.6155 0.084 Uiso 1 1 calc R . . C2 C 0.8041(4) 0.1028(2) 0.68708(16) 0.0846(8) Uani 1 1 d . . . H2 H 0.8199 0.1337 0.7315 0.101 Uiso 1 1 calc R . . C3 C 0.7546(4) 0.0252(2) 0.69154(17) 0.0852(8) Uani 1 1 d . . . H3 H 0.7386 0.0053 0.7390 0.102 Uiso 1 1 calc R . . C4 C 0.7288(3) -0.02264(17) 0.62837(17) 0.0764(7) Uani 1 1 d . . . H4 H 0.6962 -0.0747 0.6319 0.092 Uiso 1 1 calc R . . C5 C 0.7534(3) 0.00978(13) 0.55813(14) 0.0611(5) Uani 1 1 d . . . C6 C 0.8047(3) 0.08796(13) 0.55192(13) 0.0581(5) Uani 1 1 d . . . C7 C 0.8110(3) 0.10011(12) 0.47105(13) 0.0575(5) Uani 1 1 d . . . C8 C 0.7645(3) 0.02840(13) 0.43282(14) 0.0590(5) Uani 1 1 d . . . C9 C 0.6837(3) -0.10681(14) 0.46980(19) 0.0803(7) Uani 1 1 d . . . H9A H 0.5710 -0.1102 0.4312 0.120 Uiso 1 1 calc R . . H9C H 0.6660 -0.1318 0.5167 0.120 Uiso 1 1 calc R . . H9B H 0.7827 -0.1322 0.4510 0.120 Uiso 1 1 calc R . . C10 C 0.7533(3) 0.00512(15) 0.35070(15) 0.0716(6) Uani 1 1 d . . . H10A H 0.6753 0.0412 0.3172 0.107 Uiso 1 1 calc R . . H10B H 0.7017 -0.0464 0.3427 0.107 Uiso 1 1 calc R . . H10C H 0.8758 0.0055 0.3390 0.107 Uiso 1 1 calc R . . C11 C 0.8630(3) 0.17142(13) 0.43844(13) 0.0609(5) Uani 1 1 d . . . C12 C 0.8430(3) 0.17796(13) 0.35059(14) 0.0620(5) Uani 1 1 d . . . C13 C 0.6591(3) 0.19942(12) 0.30285(13) 0.0581(5) Uani 1 1 d . . . C14 C 0.6342(4) 0.19573(15) 0.22246(14) 0.0758(6) Uani 1 1 d . . . H14 H 0.7317 0.1799 0.1994 0.091 Uiso 1 1 calc R . . C15 C 0.4656(5) 0.21554(19) 0.17699(17) 0.0933(9) Uani 1 1 d . . . H15 H 0.4487 0.2126 0.1231 0.112 Uiso 1 1 calc R . . C16 C 0.3232(4) 0.23942(19) 0.2106(2) 0.0953(9) Uani 1 1 d . . . H16 H 0.2096 0.2529 0.1794 0.114 Uiso 1 1 calc R . . C17 C 0.3459(4) 0.24376(16) 0.2903(2) 0.0839(8) Uani 1 1 d . . . H17 H 0.2482 0.2603 0.3129 0.101 Uiso 1 1 calc R . . C18 C 0.5138(3) 0.22351(14) 0.33640(15) 0.0669(6) Uani 1 1 d . . . H18 H 0.5294 0.2261 0.3902 0.080 Uiso 1 1 calc R . . C19 C 0.9076(4) 0.37394(14) 0.51770(15) 0.0746(7) Uani 1 1 d . . . C20 C 0.7184(5) 0.37766(17) 0.5102(2) 0.0991(9) Uani 1 1 d . . . H20 H 0.6426 0.3444 0.4758 0.119 Uiso 1 1 calc R . . C21 C 0.6402(6) 0.4298(2) 0.5529(3) 0.1128(11) Uani 1 1 d . . . H21 H 0.5115 0.4314 0.5476 0.135 Uiso 1 1 calc R . . C22 C 0.7500(7) 0.48068(18) 0.60418(18) 0.1029(11) Uani 1 1 d . . . C23 C 0.9364(7) 0.4748(2) 0.6112(2) 0.1188(13) Uani 1 1 d . . . H23 H 1.0123 0.5077 0.6460 0.143 Uiso 1 1 calc R . . C24 C 1.0191(5) 0.42227(19) 0.56919(19) 0.0994(9) Uani 1 1 d . . . H24 H 1.1480 0.4197 0.5757 0.119 Uiso 1 1 calc R . . C25 C 0.6621(9) 0.5401(3) 0.6490(2) 0.1505(19) Uani 1 1 d . . . H25B H 0.6287 0.5855 0.6173 0.226 Uiso 1 1 calc R . . H25C H 0.7491 0.5543 0.6953 0.226 Uiso 1 1 calc R . . H25A H 0.5526 0.5182 0.6627 0.226 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 0.0841(4) 0.0638(4) 0.0652(3) 0.0034(3) -0.0087(3) -0.0105(3) O1 0.0635(10) 0.0992(13) 0.0841(11) 0.0001(9) 0.0158(9) 0.0074(9) O2 0.1171(14) 0.0725(11) 0.0652(10) 0.0068(8) -0.0039(10) -0.0182(10) O3 0.0768(12) 0.0990(14) 0.1000(14) -0.0018(11) -0.0050(10) -0.0155(10) N1 0.0523(9) 0.0542(10) 0.0766(12) 0.0001(9) 0.0023(8) 0.0038(8) N2 0.0805(12) 0.0581(11) 0.0624(11) 0.0022(9) -0.0100(9) -0.0014(9) C1 0.0643(13) 0.0806(16) 0.0597(14) -0.0042(11) -0.0015(11) 0.0088(11) C2 0.0723(16) 0.115(2) 0.0613(15) -0.0081(15) 0.0016(12) 0.0135(15) C3 0.0690(15) 0.117(2) 0.0668(16) 0.0169(16) 0.0071(12) 0.0077(15) C4 0.0549(13) 0.0869(17) 0.0835(18) 0.0188(15) 0.0045(11) 0.0060(12) C5 0.0448(10) 0.0664(14) 0.0680(14) 0.0094(11) 0.0015(9) 0.0083(9) C6 0.0449(10) 0.0636(13) 0.0609(13) 0.0011(10) -0.0012(9) 0.0100(9) C7 0.0527(11) 0.0570(12) 0.0583(12) -0.0009(9) 0.0000(9) 0.0059(9) C8 0.0433(10) 0.0606(13) 0.0683(13) -0.0023(11) -0.0004(9) 0.0063(9) C9 0.0638(14) 0.0576(14) 0.114(2) -0.0020(13) 0.0053(14) -0.0013(11) C10 0.0659(13) 0.0733(15) 0.0708(15) -0.0144(11) 0.0018(11) 0.0031(11) C11 0.0525(11) 0.0622(13) 0.0623(12) 0.0024(10) -0.0026(9) 0.0063(9) C12 0.0578(12) 0.0586(13) 0.0650(13) -0.0019(10) 0.0012(10) -0.0031(10) C13 0.0580(12) 0.0531(12) 0.0588(12) -0.0001(9) 0.0008(9) -0.0021(9) C14 0.0843(16) 0.0766(16) 0.0616(14) -0.0004(12) 0.0030(12) 0.0024(12) C15 0.099(2) 0.103(2) 0.0646(15) 0.0038(14) -0.0173(15) 0.0084(17) C16 0.0753(18) 0.096(2) 0.098(2) 0.0136(17) -0.0234(16) 0.0065(15) C17 0.0583(14) 0.0811(17) 0.108(2) 0.0073(15) 0.0060(14) 0.0023(12) C18 0.0588(13) 0.0693(14) 0.0696(14) 0.0015(11) 0.0054(11) -0.0022(10) C19 0.0910(18) 0.0552(13) 0.0659(14) 0.0090(11) -0.0121(12) -0.0100(12) C20 0.104(2) 0.0668(17) 0.121(2) -0.0159(17) 0.0081(19) -0.0106(15) C21 0.126(3) 0.075(2) 0.142(3) 0.003(2) 0.039(2) -0.0025(19) C22 0.178(4) 0.0668(18) 0.0641(17) 0.0156(14) 0.026(2) 0.015(2) C23 0.176(4) 0.087(2) 0.073(2) -0.0134(16) -0.024(2) 0.007(2) C24 0.113(2) 0.0847(19) 0.0823(18) -0.0129(16) -0.0247(16) -0.0072(17) C25 0.259(6) 0.114(3) 0.085(2) 0.008(2) 0.052(3) 0.041(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 S1 O2 1.4265(19) . ? S1 O3 1.431(2) . ? S1 N2 1.633(2) . ? S1 C19 1.759(3) . ? O1 C12 1.213(3) . ? N1 C8 1.355(3) . ? N1 C5 1.380(3) . ? N1 C9 1.467(3) . ? N2 C11 1.311(3) . ? C1 C2 1.383(4) . ? C1 C6 1.396(3) . ? C1 H1 0.9300 . ? C2 C3 1.386(4) . ? C2 H2 0.9300 . ? C3 C4 1.362(4) . ? C3 H3 0.9300 . ? C4 C5 1.397(4) . ? C4 H4 0.9300 . ? C5 C6 1.403(3) . ? C6 C7 1.445(3) . ? C7 C8 1.410(3) . ? C7 C11 1.434(3) . ? C8 C10 1.482(4) . ? C9 H9A 0.9600 . ? C9 H9C 0.9600 . ? C9 H9B 0.9600 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 C12 1.524(3) . ? C12 C13 1.485(3) . ? C13 C18 1.379(3) . ? C13 C14 1.388(4) . ? C14 C15 1.374(4) . ? C14 H14 0.9300 . ? C15 C16 1.360(5) . ? C15 H15 0.9300 . ? C16 C17 1.378(5) . ? C16 H16 0.9300 . ? C17 C18 1.376(4) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? C19 C20 1.369(5) . ? C19 C24 1.370(4) . ? C20 C21 1.365(5) . ? C20 H20 0.9300 . ? C21 C22 1.389(6) . ? C21 H21 0.9300 . ? C22 C23 1.351(6) . ? C22 C25 1.508(5) . ? C23 C24 1.380(6) . ? C23 H23 0.9300 . ? C24 H24 0.9300 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? C25 H25A 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 S1 O3 117.33(13) . . ? O2 S1 N2 113.17(10) . . ? O3 S1 N2 107.35(11) . . ? O2 S1 C19 108.55(12) . . ? O3 S1 C19 109.05(13) . . ? N2 S1 C19 99.94(11) . . ? C8 N1 C5 109.97(18) . . ? C8 N1 C9 125.6(2) . . ? C5 N1 C9 124.4(2) . . ? C11 N2 S1 123.15(17) . . ? C2 C1 C6 118.4(3) . . ? C2 C1 H1 120.8 . . ? C6 C1 H1 120.8 . . ? C1 C2 C3 121.3(3) . . ? C1 C2 H2 119.4 . . ? C3 C2 H2 119.4 . . ? C4 C3 C2 121.9(3) . . ? C4 C3 H3 119.0 . . ? C2 C3 H3 119.0 . . ? C3 C4 C5 117.2(3) . . ? C3 C4 H4 121.4 . . ? C5 C4 H4 121.4 . . ? N1 C5 C4 129.1(2) . . ? N1 C5 C6 108.67(19) . . ? C4 C5 C6 122.2(2) . . ? C1 C6 C5 119.0(2) . . ? C1 C6 C7 134.9(2) . . ? C5 C6 C7 106.0(2) . . ? C8 C7 C11 127.8(2) . . ? C8 C7 C6 106.84(19) . . ? C11 C7 C6 125.4(2) . . ? N1 C8 C7 108.5(2) . . ? N1 C8 C10 120.2(2) . . ? C7 C8 C10 131.2(2) . . ? N1 C9 H9A 109.5 . . ? N1 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? N1 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? H9C C9 H9B 109.5 . . ? C8 C10 H10A 109.5 . . ? C8 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C8 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N2 C11 C7 117.6(2) . . ? N2 C11 C12 123.2(2) . . ? C7 C11 C12 119.16(19) . . ? O1 C12 C13 123.4(2) . . ? O1 C12 C11 117.7(2) . . ? C13 C12 C11 118.87(19) . . ? C18 C13 C14 119.5(2) . . ? C18 C13 C12 121.7(2) . . ? C14 C13 C12 118.9(2) . . ? C15 C14 C13 120.0(3) . . ? C15 C14 H14 120.0 . . ? C13 C14 H14 120.0 . . ? C16 C15 C14 120.2(3) . . ? C16 C15 H15 119.9 . . ? C14 C15 H15 119.9 . . ? C15 C16 C17 120.6(3) . . ? C15 C16 H16 119.7 . . ? C17 C16 H16 119.7 . . ? C18 C17 C16 119.7(3) . . ? C18 C17 H17 120.1 . . ? C16 C17 H17 120.1 . . ? C17 C18 C13 120.1(2) . . ? C17 C18 H18 120.0 . . ? C13 C18 H18 120.0 . . ? C20 C19 C24 119.7(3) . . ? C20 C19 S1 119.8(2) . . ? C24 C19 S1 120.4(3) . . ? C21 C20 C19 120.4(3) . . ? C21 C20 H20 119.8 . . ? C19 C20 H20 119.8 . . ? C20 C21 C22 121.0(4) . . ? C20 C21 H21 119.5 . . ? C22 C21 H21 119.5 . . ? C23 C22 C21 117.2(3) . . ? C23 C22 C25 122.2(4) . . ? C21 C22 C25 120.6(5) . . ? C22 C23 C24 123.0(3) . . ? C22 C23 H23 118.5 . . ? C24 C23 H23 118.5 . . ? C19 C24 C23 118.6(4) . . ? C19 C24 H24 120.7 . . ? C23 C24 H24 120.7 . . ? C22 C25 H25B 109.5 . . ? C22 C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C22 C25 H25A 109.5 . . ? H25B C25 H25A 109.5 . . ? H25C C25 H25A 109.5 . . ? _diffrn_measured_fraction_theta_max 0.959 _diffrn_reflns_theta_full 67.14 _diffrn_measured_fraction_theta_full 0.959 _refine_diff_density_max 0.172 _refine_diff_density_min -0.240 _refine_diff_density_rms 0.030 data_100714_hell0709 _database_code_depnum_ccdc_archive 'CCDC 784634' #TrackingRef 'N-(2-hydroxy-4-methyl-2-phenyl- #2,3-dihydrocyclopenta[b]indol-1(4H)-ylidene)- #4-methylbenzenesulfonamide.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C25 H22 N2 O3 S' _chemical_formula_sum 'C25 H22 N2 O3 S' _chemical_formula_weight 430.51 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' O O 0.0106 0.0060 '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' _symmetry_space_group_name_Hall '-P 2yn' 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 12.0185(4) _cell_length_b 12.5790(5) _cell_length_c 14.3185(5) _cell_angle_alpha 90.00 _cell_angle_beta 98.130(3) _cell_angle_gamma 90.00 _cell_volume 2142.92(13) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4082 _cell_measurement_theta_min 3.2325 _cell_measurement_theta_max 29.2252 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.334 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 904 _exptl_absorpt_coefficient_mu 0.181 _exptl_absorpt_correction_type multi-scan' _exptl_absorpt_correction_T_min 0.921 _exptl_absorpt_correction_T_max 0.954 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.53 (release 17-11-2009 CrysAlis171 .NET) (compiled Nov 17 2009,16:58:22) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.3592 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10438 _diffrn_reflns_av_R_equivalents 0.0288 _diffrn_reflns_av_sigmaI/netI 0.0434 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.24 _diffrn_reflns_theta_max 25.35 _reflns_number_total 3915 _reflns_number_gt 2656 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) ; _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) ; _computing_molecular_graphics ; OLEX2: a complete structure solution, refinement and analysis program. Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341 ; _computing_publication_material ; OLEX2: a complete structure solution, refinement and analysis program. Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341 ; _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^)+(0.0630P)^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 0.0067(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3915 _refine_ls_number_parameters 284 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0649 _refine_ls_R_factor_gt 0.0401 _refine_ls_wR_factor_ref 0.1093 _refine_ls_wR_factor_gt 0.1022 _refine_ls_goodness_of_fit_ref 0.980 _refine_ls_restrained_S_all 0.980 _refine_ls_shift/su_max 0.003 _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 0.30691(4) 0.74131(4) 0.05354(4) 0.04007(18) Uani 1 1 d . . . O1 O 0.42367(12) 0.41867(12) 0.03267(9) 0.0482(4) Uani 1 1 d . . . H1 H 0.4725 0.3733 0.0449 0.072 Uiso 1 1 calc R . . O2 O 0.21104(12) 0.74290(11) -0.01806(11) 0.0572(4) Uani 1 1 d . . . O3 O 0.29494(12) 0.78936(12) 0.14244(11) 0.0562(4) Uani 1 1 d . . . N1 N 0.07489(13) 0.38878(13) 0.13716(11) 0.0422(4) Uani 1 1 d . . . N2 N 0.35930(13) 0.62346(13) 0.07032(12) 0.0421(4) Uani 1 1 d . . . C1 C 0.03361(17) 0.67053(17) 0.11152(14) 0.0455(5) Uani 1 1 d . . . H1A H 0.0779 0.7301 0.1054 0.055 Uiso 1 1 calc R . . C2 C -0.08007(18) 0.6811(2) 0.11511(16) 0.0559(6) Uani 1 1 d . . . H2 H -0.1119 0.7486 0.1108 0.067 Uiso 1 1 calc R . . C3 C -0.14764(18) 0.5944(2) 0.12486(16) 0.0579(6) Uani 1 1 d . . . H3 H -0.2241 0.6044 0.1261 0.069 Uiso 1 1 calc R . . C4 C -0.10356(17) 0.4932(2) 0.13278(15) 0.0522(6) Uani 1 1 d . . . H4 H -0.1487 0.4344 0.1395 0.063 Uiso 1 1 calc R . . C5 C 0.01071(15) 0.48242(17) 0.13026(13) 0.0408(5) Uani 1 1 d . . . C6 C 0.08086(15) 0.56954(16) 0.11721(13) 0.0376(5) Uani 1 1 d . . . C7 C 0.19137(15) 0.52398(15) 0.11467(13) 0.0348(5) Uani 1 1 d . . . C8 C 0.18034(15) 0.41540(16) 0.12730(13) 0.0364(5) Uani 1 1 d . . . C9 C 0.28240(16) 0.35187(15) 0.12269(15) 0.0418(5) Uani 1 1 d . . . H9A H 0.2731 0.3050 0.0684 0.050 Uiso 1 1 calc R . . H9B H 0.3021 0.3100 0.1795 0.050 Uiso 1 1 calc R . . C10 C 0.30309(15) 0.54358(15) 0.09678(13) 0.0342(5) Uani 1 1 d . . . C11 C 0.37125(15) 0.43810(15) 0.11357(13) 0.0354(5) Uani 1 1 d . . . C12 C 0.45534(16) 0.45454(15) 0.20235(13) 0.0368(5) Uani 1 1 d . . . C13 C 0.5639(2) 0.4848(2) 0.19857(17) 0.0749(8) Uani 1 1 d . . . H13 H 0.5900 0.4886 0.1405 0.090 Uiso 1 1 calc R . . C14 C 0.6354(2) 0.5097(3) 0.2799(2) 0.0896(10) Uani 1 1 d . . . H14 H 0.7090 0.5298 0.2756 0.108 Uiso 1 1 calc R . . C15 C 0.6007(2) 0.5053(2) 0.36519(19) 0.0686(7) Uani 1 1 d . . . H15 H 0.6485 0.5247 0.4194 0.082 Uiso 1 1 calc R . . C16 C 0.4930(2) 0.4716(2) 0.37032(17) 0.0737(8) Uani 1 1 d . . . H16 H 0.4684 0.4656 0.4288 0.088 Uiso 1 1 calc R . . C17 C 0.42106(18) 0.44679(19) 0.28967(15) 0.0549(6) Uani 1 1 d . . . H17 H 0.3483 0.4244 0.2944 0.066 Uiso 1 1 calc R . . C18 C 0.03353(19) 0.28139(18) 0.14837(17) 0.0549(6) Uani 1 1 d . . . H18A H 0.0011 0.2541 0.0880 0.082 Uiso 1 1 calc R . . H18C H -0.0225 0.2827 0.1899 0.082 Uiso 1 1 calc R . . H18B H 0.0947 0.2366 0.1746 0.082 Uiso 1 1 calc R . . C19 C 0.41807(16) 0.80319(15) 0.00680(14) 0.0370(5) Uani 1 1 d . . . C20 C 0.41222(19) 0.81618(18) -0.08881(16) 0.0535(6) Uani 1 1 d . . . H20 H 0.3482 0.7951 -0.1288 0.064 Uiso 1 1 calc R . . C21 C 0.5014(2) 0.86055(19) -0.12553(17) 0.0595(6) Uani 1 1 d . . . H21 H 0.4967 0.8690 -0.1905 0.071 Uiso 1 1 calc R . . C22 C 0.59668(19) 0.89249(16) -0.06885(17) 0.0485(6) Uani 1 1 d . . . C23 C 0.60100(19) 0.8796(2) 0.02682(17) 0.0593(7) Uani 1 1 d . . . H23 H 0.6649 0.9012 0.0667 0.071 Uiso 1 1 calc R . . C24 C 0.51255(18) 0.83526(19) 0.06515(16) 0.0561(6) Uani 1 1 d . . . H24 H 0.5170 0.8272 0.1301 0.067 Uiso 1 1 calc R . . C25 C 0.6947(2) 0.9391(2) -0.1104(2) 0.0731(8) Uani 1 1 d . . . H25A H 0.6951 0.9115 -0.1729 0.110 Uiso 1 1 calc R . . H25B H 0.7636 0.9203 -0.0715 0.110 Uiso 1 1 calc R . . H25C H 0.6876 1.0151 -0.1131 0.110 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 0.0311(3) 0.0374(3) 0.0528(3) 0.0063(2) 0.0097(2) -0.0003(2) O1 0.0463(9) 0.0580(10) 0.0431(8) -0.0004(7) 0.0167(7) 0.0099(7) O2 0.0332(8) 0.0615(10) 0.0744(11) 0.0179(8) -0.0017(7) -0.0029(7) O3 0.0565(10) 0.0535(9) 0.0647(10) -0.0060(8) 0.0294(8) -0.0012(7) N1 0.0356(10) 0.0470(10) 0.0448(10) -0.0027(8) 0.0089(8) -0.0129(8) N2 0.0336(9) 0.0374(10) 0.0574(11) 0.0096(8) 0.0137(8) 0.0009(8) C1 0.0370(12) 0.0517(14) 0.0493(13) 0.0036(10) 0.0115(9) 0.0034(10) C2 0.0410(13) 0.0691(16) 0.0591(15) 0.0061(12) 0.0122(11) 0.0129(12) C3 0.0300(12) 0.0881(19) 0.0565(15) -0.0010(13) 0.0093(10) 0.0017(13) C4 0.0333(12) 0.0731(17) 0.0506(14) -0.0039(12) 0.0079(10) -0.0115(11) C5 0.0311(11) 0.0559(13) 0.0356(11) -0.0044(10) 0.0059(9) -0.0045(10) C6 0.0302(10) 0.0503(13) 0.0332(11) -0.0004(9) 0.0074(8) -0.0008(10) C7 0.0329(11) 0.0385(11) 0.0340(11) -0.0004(8) 0.0083(8) -0.0035(9) C8 0.0334(11) 0.0421(12) 0.0340(11) -0.0024(9) 0.0063(8) -0.0063(9) C9 0.0429(12) 0.0372(11) 0.0463(12) -0.0014(9) 0.0094(9) -0.0033(9) C10 0.0320(10) 0.0382(11) 0.0327(11) -0.0007(8) 0.0061(8) -0.0023(9) C11 0.0342(10) 0.0371(11) 0.0370(11) 0.0001(9) 0.0123(8) -0.0001(9) C12 0.0376(11) 0.0335(11) 0.0401(12) 0.0042(9) 0.0089(9) 0.0031(9) C13 0.0483(14) 0.130(2) 0.0461(15) 0.0138(14) 0.0069(11) -0.0292(15) C14 0.0541(16) 0.148(3) 0.0642(19) 0.0140(18) -0.0022(14) -0.0398(18) C15 0.0628(17) 0.0862(19) 0.0514(16) -0.0021(13) -0.0107(13) -0.0007(14) C16 0.0643(17) 0.117(2) 0.0403(14) -0.0086(14) 0.0104(12) 0.0157(16) C17 0.0418(13) 0.0798(17) 0.0448(14) -0.0023(11) 0.0120(10) 0.0029(12) C18 0.0484(13) 0.0554(14) 0.0605(15) 0.0022(11) 0.0070(11) -0.0197(11) C19 0.0352(11) 0.0318(11) 0.0449(12) 0.0035(9) 0.0086(9) -0.0016(9) C20 0.0469(13) 0.0632(15) 0.0488(14) 0.0077(11) 0.0015(11) -0.0089(11) C21 0.0670(16) 0.0680(16) 0.0462(14) 0.0125(12) 0.0175(12) -0.0095(13) C22 0.0526(14) 0.0321(11) 0.0652(15) 0.0001(10) 0.0241(11) -0.0052(10) C23 0.0468(14) 0.0723(17) 0.0603(16) -0.0091(12) 0.0129(11) -0.0247(12) C24 0.0490(13) 0.0773(17) 0.0428(13) -0.0014(11) 0.0095(10) -0.0194(12) C25 0.0783(19) 0.0568(16) 0.095(2) -0.0013(14) 0.0486(15) -0.0165(13) _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 1.4300(15) . ? S1 O3 1.4346(15) . ? S1 N2 1.6152(17) . ? S1 C19 1.758(2) . ? O1 C11 1.416(2) . ? O1 H1 0.8200 . ? N1 C8 1.337(2) . ? N1 C5 1.404(3) . ? N1 C18 1.456(3) . ? N2 C10 1.297(2) . ? C1 C2 1.381(3) . ? C1 C6 1.389(3) . ? C1 H1A 0.9300 . ? C2 C3 1.379(3) . ? C2 H2 0.9300 . ? C3 C4 1.377(3) . ? C3 H3 0.9300 . ? C4 C5 1.385(3) . ? C4 H4 0.9300 . ? C5 C6 1.411(3) . ? C6 C7 1.452(3) . ? C7 C8 1.387(3) . ? C7 C10 1.424(3) . ? C8 C9 1.473(3) . ? C9 C11 1.540(3) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.560(3) . ? C11 C12 1.522(3) . ? C12 C13 1.368(3) . ? C12 C17 1.374(3) . ? C13 C14 1.381(3) . ? C13 H13 0.9300 . ? C14 C15 1.347(4) . ? C14 H14 0.9300 . ? C15 C16 1.374(4) . ? C15 H15 0.9300 . ? C16 C17 1.377(3) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C18 H18A 0.9600 . ? C18 H18C 0.9600 . ? C18 H18B 0.9600 . ? C19 C20 1.371(3) . ? C19 C24 1.372(3) . ? C20 C21 1.377(3) . ? C20 H20 0.9300 . ? C21 C22 1.367(3) . ? C21 H21 0.9300 . ? C22 C23 1.373(3) . ? C22 C25 1.511(3) . ? C23 C24 1.381(3) . ? C23 H23 0.9300 . ? C24 H24 0.9300 . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 S1 O3 117.29(10) . . ? O2 S1 N2 112.16(9) . . ? O3 S1 N2 109.91(9) . . ? O2 S1 C19 107.43(9) . . ? O3 S1 C19 109.15(9) . . ? N2 S1 C19 99.31(9) . . ? C11 O1 H1 109.5 . . ? C8 N1 C5 107.58(16) . . ? C8 N1 C18 125.96(18) . . ? C5 N1 C18 126.39(17) . . ? C10 N2 S1 123.12(14) . . ? C2 C1 C6 119.0(2) . . ? C2 C1 H1A 120.5 . . ? C6 C1 H1A 120.5 . . ? C3 C2 C1 121.8(2) . . ? C3 C2 H2 119.1 . . ? C1 C2 H2 119.1 . . ? C4 C3 C2 121.0(2) . . ? C4 C3 H3 119.5 . . ? C2 C3 H3 119.5 . . ? C3 C4 C5 117.4(2) . . ? C3 C4 H4 121.3 . . ? C5 C4 H4 121.3 . . ? C4 C5 N1 128.1(2) . . ? C4 C5 C6 122.7(2) . . ? N1 C5 C6 109.16(16) . . ? C1 C6 C5 118.10(18) . . ? C1 C6 C7 136.67(18) . . ? C5 C6 C7 105.23(17) . . ? C8 C7 C10 107.70(17) . . ? C8 C7 C6 106.31(16) . . ? C10 C7 C6 145.66(18) . . ? N1 C8 C7 111.71(17) . . ? N1 C8 C9 132.56(18) . . ? C7 C8 C9 115.65(17) . . ? C8 C9 C11 102.32(15) . . ? C8 C9 H9A 111.3 . . ? C11 C9 H9A 111.3 . . ? C8 C9 H9B 111.3 . . ? C11 C9 H9B 111.3 . . ? H9A C9 H9B 109.2 . . ? N2 C10 C7 136.91(18) . . ? N2 C10 C11 114.85(16) . . ? C7 C10 C11 108.24(16) . . ? O1 C11 C12 112.77(15) . . ? O1 C11 C9 109.99(15) . . ? C12 C11 C9 114.28(15) . . ? O1 C11 C10 107.78(14) . . ? C12 C11 C10 106.58(14) . . ? C9 C11 C10 104.88(14) . . ? C13 C12 C17 117.79(19) . . ? C13 C12 C11 121.95(18) . . ? C17 C12 C11 120.08(18) . . ? C12 C13 C14 120.8(2) . . ? C12 C13 H13 119.6 . . ? C14 C13 H13 119.6 . . ? C15 C14 C13 121.3(2) . . ? C15 C14 H14 119.3 . . ? C13 C14 H14 119.3 . . ? C14 C15 C16 118.4(2) . . ? C14 C15 H15 120.8 . . ? C16 C15 H15 120.8 . . ? C15 C16 C17 120.6(2) . . ? C15 C16 H16 119.7 . . ? C17 C16 H16 119.7 . . ? C12 C17 C16 120.9(2) . . ? C12 C17 H17 119.5 . . ? C16 C17 H17 119.5 . . ? N1 C18 H18A 109.5 . . ? N1 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? N1 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? H18C C18 H18B 109.5 . . ? C20 C19 C24 119.63(19) . . ? C20 C19 S1 119.90(15) . . ? C24 C19 S1 120.43(16) . . ? C19 C20 C21 119.8(2) . . ? C19 C20 H20 120.1 . . ? C21 C20 H20 120.1 . . ? C22 C21 C20 121.6(2) . . ? C22 C21 H21 119.2 . . ? C20 C21 H21 119.2 . . ? C21 C22 C23 117.9(2) . . ? C21 C22 C25 121.0(2) . . ? C23 C22 C25 121.1(2) . . ? C22 C23 C24 121.4(2) . . ? C22 C23 H23 119.3 . . ? C24 C23 H23 119.3 . . ? C19 C24 C23 119.6(2) . . ? C19 C24 H24 120.2 . . ? C23 C24 H24 120.2 . . ? C22 C25 H25A 109.5 . . ? C22 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C22 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.225 _refine_diff_density_min -0.307 _refine_diff_density_rms 0.039