# 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_tr1a #TrackingRef '19082_web_deposit_cif_file_2_DineshChauhan_1364820399.DC-31.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H24 N2 O2 S' _chemical_formula_sum 'C24 H24 N2 O2 S' _chemical_formula_weight 404.52 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 20.925(3) _cell_length_b 11.0264(14) _cell_length_c 18.650(2) _cell_angle_alpha 90.00 _cell_angle_beta 92.884(5) _cell_angle_gamma 90.00 _cell_volume 4297.6(10) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 1.95 _cell_measurement_theta_max 28.53 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.245 _exptl_crystal_size_mid 0.171 _exptl_crystal_size_min 0.035 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.250 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1712 _exptl_absorpt_coefficient_mu 0.173 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.965 _exptl_absorpt_correction_T_max 0.994 _exptl_absorpt_process_details 'multi-scan absorption correction' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 34628 _diffrn_reflns_av_R_equivalents 0.0718 _diffrn_reflns_av_sigmaI/netI 0.0433 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 28.53 _reflns_number_total 5462 _reflns_number_gt 4242 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0722P)^2^+5.0324P] 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 0.0010(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5425 _refine_ls_number_parameters 264 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0677 _refine_ls_R_factor_gt 0.0506 _refine_ls_wR_factor_ref 0.1503 _refine_ls_wR_factor_gt 0.1364 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.55599(2) 0.69372(4) 0.12311(2) 0.02947(14) Uani 1 1 d . . . O1 O 0.49601(6) 0.64441(13) 0.14329(9) 0.0423(4) Uani 1 1 d . . . O2 O 0.56242(8) 0.71611(15) 0.04764(7) 0.0468(4) Uani 1 1 d . . . N1 N 0.68181(7) 0.45374(14) 0.16278(8) 0.0293(3) Uani 1 1 d . . . N2 N 0.61523(7) 0.61670(15) 0.15882(9) 0.0316(4) Uani 1 1 d . . . C1 C 0.87689(11) 0.3647(2) 0.02252(11) 0.0470(6) Uani 1 1 d . . . H1 H 0.9145 0.3704 -0.0019 0.056 Uiso 1 1 calc R . . C2 C 0.83154(14) 0.4559(3) 0.01602(15) 0.0653(8) Uani 1 1 d . . . H17 H 0.8384 0.5225 -0.0132 0.078 Uiso 1 1 calc R . . C3 C 0.77592(13) 0.4478(2) 0.05311(14) 0.0583(7) Uani 1 1 d . . . H18 H 0.7457 0.5097 0.0489 0.070 Uiso 1 1 calc R . . C4 C 0.76485(9) 0.34916(18) 0.09621(10) 0.0323(4) Uani 1 1 d . . . C5 C 0.70458(10) 0.33668(17) 0.13693(11) 0.0349(4) Uani 1 1 d . . . H13 H 0.6714 0.3001 0.1058 0.042 Uiso 1 1 calc R . . H14 H 0.7128 0.2830 0.1776 0.042 Uiso 1 1 calc R . . C6 C 0.63034(8) 0.51036(16) 0.13332(9) 0.0262(4) Uani 1 1 d . . . C7 C 0.56853(8) 0.83299(16) 0.16840(9) 0.0248(3) Uani 1 1 d . . . C8 C 0.57828(8) 0.83533(17) 0.24268(9) 0.0277(4) Uani 1 1 d . . . H5 H 0.5796 0.7637 0.2690 0.033 Uiso 1 1 calc R . . C9 C 0.58603(8) 0.94657(18) 0.27679(10) 0.0302(4) Uani 1 1 d . . . H4 H 0.5930 0.9488 0.3264 0.036 Uiso 1 1 calc R . . C10 C 0.58361(9) 1.05463(18) 0.23856(11) 0.0331(4) Uani 1 1 d . . . C11 C 0.59154(12) 1.1742(2) 0.27700(14) 0.0494(6) Uani 1 1 d . . . H3 H 0.5642 1.1763 0.3168 0.074 Uiso 1 1 calc R . . H24 H 0.5802 1.2391 0.2444 0.074 Uiso 1 1 calc R . . H2 H 0.6353 1.1835 0.2942 0.074 Uiso 1 1 calc R . . C12 C 0.72033(8) 0.50796(18) 0.22250(10) 0.0307(4) Uani 1 1 d . . . H12 H 0.7107 0.5938 0.2253 0.037 Uiso 1 1 calc R . . H11 H 0.7654 0.4996 0.2134 0.037 Uiso 1 1 calc R . . C13 C 0.70740(8) 0.44855(17) 0.29329(10) 0.0282(4) Uani 1 1 d . . . C14 C 0.64939(9) 0.46754(18) 0.32535(11) 0.0334(4) Uani 1 1 d . . . H10 H 0.6186 0.5179 0.3034 0.040 Uiso 1 1 calc R . . C15 C 0.63762(11) 0.4116(2) 0.38969(12) 0.0447(5) Uani 1 1 d . . . H6 H 0.5989 0.4246 0.4108 0.054 Uiso 1 1 calc R . . C16 C 0.68302(13) 0.3363(2) 0.42290(12) 0.0519(6) Uani 1 1 d . . . H9 H 0.6748 0.2989 0.4662 0.062 Uiso 1 1 calc R . . C17 C 0.74052(13) 0.3168(2) 0.39169(13) 0.0521(6) Uani 1 1 d . . . H8 H 0.7710 0.2659 0.4137 0.062 Uiso 1 1 calc R . . C18 C 0.75282(10) 0.3735(2) 0.32730(11) 0.0399(5) Uani 1 1 d . . . H7 H 0.7919 0.3610 0.3067 0.048 Uiso 1 1 calc R . . C19 C 0.86642(10) 0.2666(2) 0.06469(11) 0.0389(5) Uani 1 1 d . . . H16 H 0.8968 0.2051 0.0690 0.047 Uiso 1 1 calc R . . C20 C 0.81052(9) 0.25815(18) 0.10125(10) 0.0336(4) Uani 1 1 d . . . H15 H 0.8036 0.1904 0.1296 0.040 Uiso 1 1 calc R . . C21 C 0.59390(11) 0.44787(18) 0.07348(10) 0.0378(5) Uani 1 1 d . . . H19 H 0.6100 0.4503 0.0279 0.045 Uiso 1 1 calc R . . C22 C 0.54072(11) 0.3901(2) 0.08172(14) 0.0502(6) Uani 1 1 d . . . H21 H 0.5236 0.3864 0.1267 0.060 Uiso 1 1 calc R . . H20 H 0.5197 0.3525 0.0426 0.060 Uiso 1 1 calc R . . C23 C 0.56566(9) 0.93891(18) 0.12896(10) 0.0326(4) Uani 1 1 d . . . H23 H 0.5589 0.9364 0.0793 0.039 Uiso 1 1 calc R . . C24 C 0.57306(10) 1.04967(18) 0.16442(11) 0.0376(4) Uani 1 1 d . . . H22 H 0.5709 1.1213 0.1381 0.045 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 0.0279(2) 0.0304(2) 0.0295(2) -0.00951(18) -0.00509(16) 0.00599(17) O1 0.0252(6) 0.0333(8) 0.0677(10) -0.0143(7) -0.0033(6) 0.0016(5) O2 0.0677(10) 0.0457(9) 0.0259(7) -0.0100(6) -0.0080(7) 0.0114(8) N1 0.0303(7) 0.0290(8) 0.0289(8) -0.0035(6) 0.0042(6) 0.0055(6) N2 0.0261(7) 0.0333(8) 0.0348(8) -0.0113(7) -0.0043(6) 0.0079(6) C1 0.0496(12) 0.0626(15) 0.0302(10) -0.0002(10) 0.0152(9) 0.0178(11) C2 0.0716(17) 0.0660(18) 0.0619(16) 0.0322(14) 0.0383(14) 0.0288(14) C3 0.0627(15) 0.0538(15) 0.0614(15) 0.0305(12) 0.0320(12) 0.0343(12) C4 0.0406(10) 0.0320(10) 0.0245(9) 0.0005(7) 0.0043(7) 0.0128(8) C5 0.0419(10) 0.0280(9) 0.0353(10) 0.0017(8) 0.0082(8) 0.0103(8) C6 0.0270(8) 0.0276(9) 0.0245(8) -0.0030(7) 0.0056(6) 0.0013(7) C7 0.0223(7) 0.0282(9) 0.0241(8) -0.0061(7) 0.0030(6) 0.0019(6) C8 0.0266(8) 0.0314(9) 0.0250(9) -0.0022(7) 0.0013(6) 0.0008(7) C9 0.0288(8) 0.0379(10) 0.0239(8) -0.0072(7) 0.0025(7) -0.0017(7) C10 0.0329(9) 0.0310(10) 0.0361(10) -0.0088(8) 0.0082(8) -0.0062(7) C11 0.0593(14) 0.0342(12) 0.0550(14) -0.0152(10) 0.0051(11) -0.0081(10) C12 0.0240(8) 0.0316(10) 0.0364(10) -0.0007(8) 0.0014(7) 0.0014(7) C13 0.0255(8) 0.0278(9) 0.0309(9) -0.0058(7) -0.0016(7) -0.0018(6) C14 0.0282(9) 0.0345(10) 0.0376(10) -0.0107(8) 0.0019(7) -0.0029(7) C15 0.0447(11) 0.0538(14) 0.0366(11) -0.0189(10) 0.0109(9) -0.0175(10) C16 0.0680(16) 0.0621(16) 0.0250(10) -0.0014(10) -0.0018(10) -0.0211(13) C17 0.0615(15) 0.0559(15) 0.0371(12) 0.0068(10) -0.0147(10) 0.0022(11) C18 0.0329(10) 0.0494(13) 0.0369(11) 0.0013(9) -0.0037(8) 0.0050(9) C19 0.0398(10) 0.0439(12) 0.0327(10) -0.0090(9) -0.0022(8) 0.0188(9) C20 0.0412(10) 0.0297(10) 0.0295(9) -0.0014(8) -0.0022(7) 0.0117(8) C21 0.0567(12) 0.0313(10) 0.0247(9) -0.0085(8) -0.0027(8) 0.0064(9) C22 0.0402(11) 0.0558(14) 0.0531(14) -0.0276(11) -0.0128(10) 0.0058(10) C23 0.0396(10) 0.0344(10) 0.0243(9) -0.0022(7) 0.0078(7) 0.0000(8) C24 0.0501(12) 0.0285(10) 0.0350(10) 0.0026(8) 0.0092(9) -0.0030(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O1 1.4354(15) . ? S1 O2 1.4419(15) . ? S1 N2 1.6181(16) . ? S1 C7 1.7660(18) . ? N1 C6 1.339(2) . ? N1 C5 1.466(2) . ? N1 C12 1.469(2) . ? N2 C6 1.310(2) . ? C1 C19 1.362(3) . ? C1 C2 1.383(3) . ? C1 H1 0.9300 . ? C2 C3 1.386(3) . ? C2 H17 0.9300 . ? C3 C4 1.379(3) . ? C3 H18 0.9300 . ? C4 C20 1.386(3) . ? C4 C5 1.511(3) . ? C5 H13 0.9700 . ? C5 H14 0.9700 . ? C6 C21 1.489(3) . ? C7 C23 1.380(3) . ? C7 C8 1.390(2) . ? C8 C9 1.388(3) . ? C8 H5 0.9300 . ? C9 C10 1.388(3) . ? C9 H4 0.9300 . ? C10 C24 1.390(3) . ? C10 C11 1.506(3) . ? C11 H3 0.9600 . ? C11 H24 0.9600 . ? C11 H2 0.9600 . ? C12 C13 1.510(3) . ? C12 H12 0.9700 . ? C12 H11 0.9700 . ? C13 C18 1.389(3) . ? C13 C14 1.396(3) . ? C14 C15 1.383(3) . ? C14 H10 0.9300 . ? C15 C16 1.384(4) . ? C15 H6 0.9300 . ? C16 C17 1.379(4) . ? C16 H9 0.9300 . ? C17 C18 1.389(3) . ? C17 H8 0.9300 . ? C18 H7 0.9300 . ? C19 C20 1.386(3) . ? C19 H16 0.9300 . ? C20 H15 0.9300 . ? C21 C22 1.298(3) . ? C21 H19 0.9300 . ? C22 H21 0.9300 . ? C22 H20 0.9300 . ? C23 C24 1.394(3) . ? C23 H23 0.9300 . ? C24 H22 0.9300 . ? 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 O1 S1 O2 116.52(10) . . ? O1 S1 N2 110.81(9) . . ? O2 S1 N2 112.61(9) . . ? O1 S1 C7 108.35(8) . . ? O2 S1 C7 107.41(9) . . ? N2 S1 C7 99.63(8) . . ? C6 N1 C5 122.94(16) . . ? C6 N1 C12 121.39(15) . . ? C5 N1 C12 115.64(15) . . ? C6 N2 S1 120.95(13) . . ? C19 C1 C2 119.9(2) . . ? C19 C1 H1 120.1 . . ? C2 C1 H1 120.1 . . ? C1 C2 C3 120.0(2) . . ? C1 C2 H17 120.0 . . ? C3 C2 H17 120.0 . . ? C4 C3 C2 120.7(2) . . ? C4 C3 H18 119.6 . . ? C2 C3 H18 119.6 . . ? C3 C4 C20 118.39(19) . . ? C3 C4 C5 122.25(17) . . ? C20 C4 C5 119.35(18) . . ? N1 C5 C4 112.24(16) . . ? N1 C5 H13 109.2 . . ? C4 C5 H13 109.2 . . ? N1 C5 H14 109.2 . . ? C4 C5 H14 109.2 . . ? H13 C5 H14 107.9 . . ? N2 C6 N1 118.18(16) . . ? N2 C6 C21 124.23(16) . . ? N1 C6 C21 117.58(16) . . ? C23 C7 C8 121.05(16) . . ? C23 C7 S1 118.65(13) . . ? C8 C7 S1 120.24(14) . . ? C9 C8 C7 118.76(17) . . ? C9 C8 H5 120.6 . . ? C7 C8 H5 120.6 . . ? C8 C9 C10 121.53(17) . . ? C8 C9 H4 119.2 . . ? C10 C9 H4 119.2 . . ? C9 C10 C24 118.49(17) . . ? C9 C10 C11 120.45(18) . . ? C24 C10 C11 121.06(19) . . ? C10 C11 H3 109.5 . . ? C10 C11 H24 109.5 . . ? H3 C11 H24 109.5 . . ? C10 C11 H2 109.5 . . ? H3 C11 H2 109.5 . . ? H24 C11 H2 109.5 . . ? N1 C12 C13 111.76(15) . . ? N1 C12 H12 109.3 . . ? C13 C12 H12 109.3 . . ? N1 C12 H11 109.3 . . ? C13 C12 H11 109.3 . . ? H12 C12 H11 107.9 . . ? C18 C13 C14 118.92(18) . . ? C18 C13 C12 120.60(17) . . ? C14 C13 C12 120.48(17) . . ? C15 C14 C13 120.11(19) . . ? C15 C14 H10 119.9 . . ? C13 C14 H10 119.9 . . ? C14 C15 C16 120.5(2) . . ? C14 C15 H6 119.7 . . ? C16 C15 H6 119.7 . . ? C17 C16 C15 119.9(2) . . ? C17 C16 H9 120.1 . . ? C15 C16 H9 120.1 . . ? C16 C17 C18 119.9(2) . . ? C16 C17 H8 120.0 . . ? C18 C17 H8 120.0 . . ? C17 C18 C13 120.7(2) . . ? C17 C18 H7 119.7 . . ? C13 C18 H7 119.7 . . ? C1 C19 C20 120.09(18) . . ? C1 C19 H16 120.0 . . ? C20 C19 H16 120.0 . . ? C4 C20 C19 120.94(19) . . ? C4 C20 H15 119.5 . . ? C19 C20 H15 119.5 . . ? C22 C21 C6 123.3(2) . . ? C22 C21 H19 118.4 . . ? C6 C21 H19 118.4 . . ? C21 C22 H21 120.0 . . ? C21 C22 H20 120.0 . . ? H21 C22 H20 120.0 . . ? C7 C23 C24 119.19(17) . . ? C7 C23 H23 120.4 . . ? C24 C23 H23 120.4 . . ? C10 C24 C23 120.98(18) . . ? C10 C24 H22 119.5 . . ? C23 C24 H22 119.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 S1 N2 C6 75.83(17) . . . . ? O2 S1 N2 C6 -56.68(18) . . . . ? C7 S1 N2 C6 -170.22(15) . . . . ? C19 C1 C2 C3 0.8(5) . . . . ? C1 C2 C3 C4 -0.5(5) . . . . ? C2 C3 C4 C20 -0.3(4) . . . . ? C2 C3 C4 C5 -179.5(3) . . . . ? C6 N1 C5 C4 106.5(2) . . . . ? C12 N1 C5 C4 -71.9(2) . . . . ? C3 C4 C5 N1 -35.4(3) . . . . ? C20 C4 C5 N1 145.44(18) . . . . ? S1 N2 C6 N1 176.66(13) . . . . ? S1 N2 C6 C21 -3.4(3) . . . . ? C5 N1 C6 N2 -177.69(16) . . . . ? C12 N1 C6 N2 0.5(3) . . . . ? C5 N1 C6 C21 2.4(3) . . . . ? C12 N1 C6 C21 -179.43(16) . . . . ? O1 S1 C7 C23 -110.68(15) . . . . ? O2 S1 C7 C23 15.98(17) . . . . ? N2 S1 C7 C23 133.48(15) . . . . ? O1 S1 C7 C8 66.54(16) . . . . ? O2 S1 C7 C8 -166.80(14) . . . . ? N2 S1 C7 C8 -49.29(15) . . . . ? C23 C7 C8 C9 -0.9(3) . . . . ? S1 C7 C8 C9 -178.05(13) . . . . ? C7 C8 C9 C10 0.7(3) . . . . ? C8 C9 C10 C24 0.1(3) . . . . ? C8 C9 C10 C11 179.40(18) . . . . ? C6 N1 C12 C13 104.03(19) . . . . ? C5 N1 C12 C13 -77.63(19) . . . . ? N1 C12 C13 C18 108.3(2) . . . . ? N1 C12 C13 C14 -71.2(2) . . . . ? C18 C13 C14 C15 -0.4(3) . . . . ? C12 C13 C14 C15 179.16(18) . . . . ? C13 C14 C15 C16 -0.1(3) . . . . ? C14 C15 C16 C17 0.0(3) . . . . ? C15 C16 C17 C18 0.4(4) . . . . ? C16 C17 C18 C13 -0.8(4) . . . . ? C14 C13 C18 C17 0.8(3) . . . . ? C12 C13 C18 C17 -178.7(2) . . . . ? C2 C1 C19 C20 -0.2(4) . . . . ? C3 C4 C20 C19 0.9(3) . . . . ? C5 C4 C20 C19 -179.94(18) . . . . ? C1 C19 C20 C4 -0.6(3) . . . . ? N2 C6 C21 C22 -78.6(3) . . . . ? N1 C6 C21 C22 101.3(2) . . . . ? C8 C7 C23 C24 0.4(3) . . . . ? S1 C7 C23 C24 177.59(15) . . . . ? C9 C10 C24 C23 -0.6(3) . . . . ? C11 C10 C24 C23 -179.92(19) . . . . ? C7 C23 C24 C10 0.4(3) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 28.53 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 1.984 _refine_diff_density_min -0.479 _refine_diff_density_rms 0.065 _database_code_depnum_ccdc_archive 'CCDC 932113' ####################################################################### # # 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_tr2 #TrackingRef '19080_web_deposit_cif_file_0_DineshChauhan_1364820399.DC-02-14.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point 100 _chemical_formula_moiety 'C29 H32 N2 O4 S' _chemical_formula_sum 'C29 H32 N2 O4 S' _chemical_formula_weight 504.63 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 'P 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.7934(18) _cell_length_b 11.215(2) _cell_length_c 12.187(2) _cell_angle_alpha 90.00 _cell_angle_beta 96.377(4) _cell_angle_gamma 90.00 _cell_volume 1330.2(4) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 1.68 _cell_measurement_theta_max 28.33 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.320 _exptl_crystal_size_mid 0.184 _exptl_crystal_size_min 0.069 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.260 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 536 _exptl_absorpt_coefficient_mu 0.159 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.966 _exptl_absorpt_correction_T_max 0.989 _exptl_absorpt_process_details 'multi-scan absorption correction' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker axs (Kappa apex2)' _diffrn_measurement_method '\w and \f scan' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 19812 _diffrn_reflns_av_R_equivalents 0.0501 _diffrn_reflns_av_sigmaI/netI 0.0494 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.68 _diffrn_reflns_theta_max 28.33 _reflns_number_total 5000 _reflns_number_gt 4223 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0787P)^2^+0.1308P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0000(18) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.47(8) _refine_ls_number_reflns 3466 _refine_ls_number_parameters 329 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0622 _refine_ls_R_factor_gt 0.0496 _refine_ls_wR_factor_ref 0.1323 _refine_ls_wR_factor_gt 0.1235 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _refine_ls_shift/su_max 1.159 _refine_ls_shift/su_mean 0.004 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 0.46453(5) 0.24817(6) 0.06680(5) 0.03018(16) Uani 1 1 d . . . O1 O 0.85306(19) 0.4276(2) -0.24483(17) 0.0438(5) Uani 1 1 d . . . O2 O 0.34961(18) 0.1772(2) 0.09323(18) 0.0416(5) Uani 1 1 d . . . O3 O 0.44977(18) 0.3033(2) -0.03961(15) 0.0372(5) Uani 1 1 d . . . O4 O 0.6529(2) 0.4508(4) -0.3526(2) 0.0844(12) Uani 1 1 d . . . N1 N 0.5964(2) 0.1608(2) 0.09004(18) 0.0302(5) Uani 1 1 d . . . N2 N 0.8178(2) 0.1077(2) 0.07913(18) 0.0323(5) Uani 1 1 d . . . C1 C 0.8586(5) 0.4461(6) -0.4386(4) 0.0873(17) Uani 1 1 d . . . H1 H 0.8618 0.3605 -0.4380 0.131 Uiso 1 1 calc R . . H27 H 0.9503 0.4772 -0.4351 0.131 Uiso 1 1 calc R . . H28 H 0.8062 0.4728 -0.5054 0.131 Uiso 1 1 calc R . . C2 C 0.7924(3) 0.4891(4) -0.3415(3) 0.0509(9) Uani 1 1 d . . . C3 C 0.7490(2) 0.4194(3) -0.1711(2) 0.0329(6) Uani 1 1 d . . . H29 H 0.7588 0.4855 -0.1183 0.039 Uiso 1 1 calc R . . C4 C 0.7585(2) 0.3043(3) -0.1111(2) 0.0328(6) Uani 1 1 d . . . H30 H 0.7768 0.2352 -0.1490 0.039 Uiso 1 1 calc R . . C5 C 0.7416(2) 0.2972(3) -0.0051(2) 0.0330(6) Uani 1 1 d . . . H31 H 0.7465 0.3678 0.0351 0.040 Uiso 1 1 calc R . . C6 C 0.7157(3) 0.1865(3) 0.0546(2) 0.0295(5) Uani 1 1 d . . . C7 C 0.4905(2) 0.3606(2) 0.1675(2) 0.0278(5) Uani 1 1 d . . . C8 C 0.4988(3) 0.3305(3) 0.2792(2) 0.0333(6) Uani 1 1 d . . . H5 H 0.4951 0.2511 0.3008 0.040 Uiso 1 1 calc R . . C9 C 0.5127(3) 0.4201(3) 0.3570(2) 0.0378(6) Uani 1 1 d . . . H4 H 0.5194 0.4002 0.4315 0.045 Uiso 1 1 calc R . . C10 C 0.5168(3) 0.5396(3) 0.3269(2) 0.0349(6) Uani 1 1 d . . . C11 C 0.5293(4) 0.6381(4) 0.4117(3) 0.0534(9) Uani 1 1 d . . . H2 H 0.5146 0.6060 0.4825 0.080 Uiso 1 1 calc R . . H32 H 0.4618 0.6984 0.3909 0.080 Uiso 1 1 calc R . . H3 H 0.6195 0.6724 0.4158 0.080 Uiso 1 1 calc R . . C12 C 0.4986(2) 0.4782(3) 0.1361(2) 0.0306(6) Uani 1 1 d . . . H7 H 0.4963 0.4978 0.0618 0.037 Uiso 1 1 calc R . . C13 C 0.5102(2) 0.5665(3) 0.2151(2) 0.0335(6) Uani 1 1 d . . . H6 H 0.5137 0.6458 0.1932 0.040 Uiso 1 1 calc R . . C14 C 0.9567(2) 0.1238(3) 0.0458(2) 0.0373(6) Uani 1 1 d . . . H13 H 1.0233 0.0931 0.1037 0.045 Uiso 1 1 calc R . . H14 H 0.9741 0.2084 0.0384 0.045 Uiso 1 1 calc R . . C15 C 0.9773(2) 0.0626(3) -0.0611(2) 0.0324(6) Uani 1 1 d . . . C16 C 1.0962(3) 0.0853(4) -0.1108(3) 0.0490(9) Uani 1 1 d . . . H8 H 1.1615 0.1383 -0.0780 0.059 Uiso 1 1 calc R . . C17 C 1.1173(3) 0.0294(5) -0.2084(3) 0.0607(11) Uani 1 1 d . . . H9 H 1.1966 0.0461 -0.2411 0.073 Uiso 1 1 calc R . . C18 C 1.0237(3) -0.0501(4) -0.2580(3) 0.0556(10) Uani 1 1 d . . . H10 H 1.0396 -0.0878 -0.3234 0.067 Uiso 1 1 calc R . . C19 C 0.9062(3) -0.0736(4) -0.2101(3) 0.0512(8) Uani 1 1 d . . . H11 H 0.8415 -0.1267 -0.2435 0.061 Uiso 1 1 calc R . . C20 C 0.8838(3) -0.0187(3) -0.1126(2) 0.0409(7) Uani 1 1 d . . . H12 H 0.8044 -0.0363 -0.0804 0.049 Uiso 1 1 calc R . . C21 C 0.7926(3) -0.0021(3) 0.1382(2) 0.0359(6) Uani 1 1 d . . . H15 H 0.8640 -0.0591 0.1264 0.043 Uiso 1 1 calc R . . H16 H 0.7057 -0.0355 0.1065 0.043 Uiso 1 1 calc R . . C22 C 0.7886(3) 0.0123(3) 0.2604(2) 0.0405(7) Uani 1 1 d . . . C23 C 0.7994(4) 0.1196(4) 0.3142(3) 0.0559(9) Uani 1 1 d . . . H21 H 0.8111 0.1890 0.2746 0.067 Uiso 1 1 calc R . . C24 C 0.7930(5) 0.1262(5) 0.4276(3) 0.0766(13) Uani 1 1 d . . . H20 H 0.8008 0.1997 0.4630 0.092 Uiso 1 1 calc R . . C25 C 0.7755(4) 0.0253(6) 0.4873(3) 0.0718(13) Uani 1 1 d . . . H19 H 0.7718 0.0302 0.5631 0.086 Uiso 1 1 calc R . . C26 C 0.7636(4) -0.0807(6) 0.4363(4) 0.0777(14) Uani 1 1 d . . . H18 H 0.7512 -0.1494 0.4768 0.093 Uiso 1 1 calc R . . C27 C 0.7696(4) -0.0880(4) 0.3231(3) 0.0647(11) Uani 1 1 d . . . H17 H 0.7607 -0.1620 0.2887 0.078 Uiso 1 1 calc R . . C28 C 0.6135(3) 0.4330(3) -0.2476(2) 0.0396(7) Uani 1 1 d . . . H23 H 0.5578 0.3617 -0.2458 0.048 Uiso 1 1 calc R . . H22 H 0.5613 0.5006 -0.2254 0.048 Uiso 1 1 calc R . . C29 C 0.8056(3) 0.6208(4) -0.3264(3) 0.0558(9) Uani 1 1 d . . . H26 H 0.7622 0.6604 -0.3909 0.084 Uiso 1 1 calc R . . H24 H 0.9011 0.6421 -0.3155 0.084 Uiso 1 1 calc R . . H25 H 0.7619 0.6446 -0.2632 0.084 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 0.0250(3) 0.0291(3) 0.0356(3) -0.0019(3) -0.0005(2) 0.0012(3) O1 0.0328(9) 0.0469(14) 0.0537(13) 0.0073(11) 0.0143(8) -0.0012(9) O2 0.0278(9) 0.0367(12) 0.0598(13) -0.0015(10) 0.0027(8) -0.0036(8) O3 0.0334(9) 0.0421(12) 0.0350(10) -0.0042(9) -0.0020(7) 0.0084(8) O4 0.0441(12) 0.162(4) 0.0451(14) 0.0145(18) -0.0049(10) -0.0416(18) N1 0.0300(10) 0.0260(11) 0.0341(11) -0.0004(10) 0.0014(8) 0.0036(9) N2 0.0297(10) 0.0324(13) 0.0343(12) -0.0028(10) 0.0020(8) 0.0064(9) C1 0.088(3) 0.116(5) 0.064(3) -0.019(3) 0.032(2) -0.028(3) C2 0.0382(14) 0.076(3) 0.0386(17) -0.0041(17) 0.0059(12) -0.0161(16) C3 0.0265(11) 0.0346(15) 0.0377(14) -0.0005(12) 0.0042(9) -0.0040(10) C4 0.0295(12) 0.0303(15) 0.0384(15) -0.0025(12) 0.0033(10) -0.0005(10) C5 0.0283(11) 0.0270(14) 0.0426(15) -0.0043(12) -0.0001(10) -0.0008(10) C6 0.0301(11) 0.0294(14) 0.0283(13) -0.0033(11) -0.0005(9) 0.0025(10) C7 0.0201(10) 0.0317(14) 0.0319(13) 0.0008(11) 0.0040(9) 0.0031(9) C8 0.0341(12) 0.0322(14) 0.0339(14) 0.0039(12) 0.0056(10) 0.0016(11) C9 0.0373(13) 0.0470(18) 0.0290(14) 0.0019(13) 0.0036(10) -0.0022(12) C10 0.0290(11) 0.0380(16) 0.0379(15) -0.0064(13) 0.0045(10) -0.0002(11) C11 0.066(2) 0.052(2) 0.0414(18) -0.0090(16) 0.0039(15) -0.0088(17) C12 0.0265(11) 0.0323(15) 0.0330(14) 0.0033(11) 0.0030(9) 0.0042(10) C13 0.0277(11) 0.0296(15) 0.0429(16) 0.0023(12) 0.0017(10) 0.0011(10) C14 0.0259(11) 0.0403(17) 0.0441(16) -0.0031(14) -0.0029(10) 0.0012(11) C15 0.0230(10) 0.0385(16) 0.0345(14) 0.0044(12) -0.0019(9) 0.0030(10) C16 0.0277(12) 0.070(3) 0.0479(18) 0.0088(17) -0.0002(11) -0.0071(14) C17 0.0304(13) 0.107(3) 0.0472(19) 0.007(2) 0.0137(12) 0.0043(18) C18 0.0485(17) 0.082(3) 0.0382(17) -0.0043(18) 0.0123(13) 0.0138(18) C19 0.0505(17) 0.057(2) 0.0470(18) -0.0114(17) 0.0079(13) -0.0073(16) C20 0.0335(13) 0.0467(18) 0.0439(17) -0.0086(14) 0.0102(11) -0.0064(12) C21 0.0351(13) 0.0293(15) 0.0422(16) 0.0003(13) -0.0007(11) 0.0067(11) C22 0.0261(11) 0.052(2) 0.0423(16) 0.0054(14) 0.0000(10) -0.0011(12) C23 0.070(2) 0.052(2) 0.0445(19) -0.0008(17) 0.0026(15) 0.0142(19) C24 0.096(3) 0.083(4) 0.049(2) -0.011(2) 0.0019(19) 0.025(3) C25 0.058(2) 0.107(4) 0.052(2) 0.013(3) 0.0111(17) 0.001(2) C26 0.076(3) 0.094(4) 0.063(3) 0.020(3) 0.005(2) -0.034(3) C27 0.070(2) 0.060(3) 0.061(2) 0.012(2) -0.0065(17) -0.027(2) C28 0.0323(12) 0.0444(18) 0.0415(16) 0.0047(14) 0.0012(11) -0.0088(12) C29 0.0469(17) 0.065(3) 0.055(2) 0.0158(19) 0.0053(14) 0.0013(17) _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 1.429(2) . ? S1 O2 1.444(2) . ? S1 N1 1.620(2) . ? S1 C7 1.758(3) . ? O1 C3 1.434(3) . ? O1 C2 1.436(4) . ? O4 C28 1.391(4) . ? O4 C2 1.424(4) . ? N1 C6 1.322(3) . ? N2 C6 1.343(3) . ? N2 C21 1.461(4) . ? N2 C14 1.473(3) . ? C1 C2 1.492(5) . ? C1 H1 0.9600 . ? C1 H27 0.9600 . ? C1 H28 0.9600 . ? C2 C29 1.492(6) . ? C3 C4 1.481(4) . ? C3 C28 1.542(4) . ? C3 H29 0.9800 . ? C4 C5 1.324(4) . ? C4 H30 0.9300 . ? C5 C6 1.475(4) . ? C5 H31 0.9300 . ? C7 C12 1.378(4) . ? C7 C8 1.396(4) . ? C8 C9 1.378(4) . ? C8 H5 0.9300 . ? C9 C10 1.392(5) . ? C9 H4 0.9300 . ? C10 C13 1.390(4) . ? C10 C11 1.509(5) . ? C11 H2 0.9600 . ? C11 H32 0.9600 . ? C11 H3 0.9600 . ? C12 C13 1.377(4) . ? C12 H7 0.9300 . ? C13 H6 0.9300 . ? C14 C15 1.506(4) . ? C14 H13 0.9700 . ? C14 H14 0.9700 . ? C15 C16 1.393(4) . ? C15 C20 1.392(4) . ? C16 C17 1.381(5) . ? C16 H8 0.9300 . ? C17 C18 1.371(6) . ? C17 H9 0.9300 . ? C18 C19 1.373(4) . ? C18 H10 0.9300 . ? C19 C20 1.377(4) . ? C19 H11 0.9300 . ? C20 H12 0.9300 . ? C21 C22 1.502(4) . ? C21 H15 0.9700 . ? C21 H16 0.9700 . ? C22 C23 1.370(5) . ? C22 C27 1.384(5) . ? C23 C24 1.392(5) . ? C23 H21 0.9300 . ? C24 C25 1.366(7) . ? C24 H20 0.9300 . ? C25 C26 1.340(7) . ? C25 H19 0.9300 . ? C26 C27 1.390(6) . ? C26 H18 0.9300 . ? C27 H17 0.9300 . ? C28 H23 0.9700 . ? C28 H22 0.9700 . ? C29 H26 0.9600 . ? C29 H24 0.9600 . ? C29 H25 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 O3 S1 O2 115.98(11) . . ? O3 S1 N1 114.74(12) . . ? O2 S1 N1 104.69(12) . . ? O3 S1 C7 108.38(13) . . ? O2 S1 C7 107.19(12) . . ? N1 S1 C7 105.11(11) . . ? C3 O1 C2 106.6(2) . . ? C28 O4 C2 108.5(2) . . ? C6 N1 S1 121.8(2) . . ? C6 N2 C21 120.1(2) . . ? C6 N2 C14 123.1(3) . . ? C21 N2 C14 116.8(2) . . ? C2 C1 H1 109.5 . . ? C2 C1 H27 109.5 . . ? H1 C1 H27 109.5 . . ? C2 C1 H28 109.5 . . ? H1 C1 H28 109.5 . . ? H27 C1 H28 109.5 . . ? O4 C2 O1 103.8(3) . . ? O4 C2 C29 112.3(3) . . ? O1 C2 C29 110.6(3) . . ? O4 C2 C1 108.9(3) . . ? O1 C2 C1 108.6(4) . . ? C29 C2 C1 112.2(4) . . ? O1 C3 C4 110.8(2) . . ? O1 C3 C28 103.8(2) . . ? C4 C3 C28 112.8(2) . . ? O1 C3 H29 109.8 . . ? C4 C3 H29 109.8 . . ? C28 C3 H29 109.8 . . ? C5 C4 C3 121.8(3) . . ? C5 C4 H30 119.1 . . ? C3 C4 H30 119.1 . . ? C4 C5 C6 125.4(3) . . ? C4 C5 H31 117.3 . . ? C6 C5 H31 117.3 . . ? N1 C6 N2 116.6(3) . . ? N1 C6 C5 123.5(2) . . ? N2 C6 C5 119.9(2) . . ? C12 C7 C8 120.2(3) . . ? C12 C7 S1 120.1(2) . . ? C8 C7 S1 119.7(2) . . ? C9 C8 C7 119.1(3) . . ? C9 C8 H5 120.5 . . ? C7 C8 H5 120.5 . . ? C8 C9 C10 121.6(3) . . ? C8 C9 H4 119.2 . . ? C10 C9 H4 119.2 . . ? C9 C10 C13 118.0(3) . . ? C9 C10 C11 121.8(3) . . ? C13 C10 C11 120.3(3) . . ? C10 C11 H2 109.5 . . ? C10 C11 H32 109.5 . . ? H2 C11 H32 109.5 . . ? C10 C11 H3 109.5 . . ? H2 C11 H3 109.5 . . ? H32 C11 H3 109.5 . . ? C7 C12 C13 119.9(2) . . ? C7 C12 H7 120.1 . . ? C13 C12 H7 120.1 . . ? C12 C13 C10 121.3(3) . . ? C12 C13 H6 119.4 . . ? C10 C13 H6 119.4 . . ? N2 C14 C15 113.5(2) . . ? N2 C14 H13 108.9 . . ? C15 C14 H13 108.9 . . ? N2 C14 H14 108.9 . . ? C15 C14 H14 108.9 . . ? H13 C14 H14 107.7 . . ? C16 C15 C20 117.7(3) . . ? C16 C15 C14 119.4(3) . . ? C20 C15 C14 122.9(2) . . ? C17 C16 C15 120.2(3) . . ? C17 C16 H8 119.9 . . ? C15 C16 H8 119.9 . . ? C18 C17 C16 121.3(3) . . ? C18 C17 H9 119.4 . . ? C16 C17 H9 119.4 . . ? C17 C18 C19 119.2(3) . . ? C17 C18 H10 120.4 . . ? C19 C18 H10 120.4 . . ? C18 C19 C20 120.2(3) . . ? C18 C19 H11 119.9 . . ? C20 C19 H11 119.9 . . ? C19 C20 C15 121.4(3) . . ? C19 C20 H12 119.3 . . ? C15 C20 H12 119.3 . . ? N2 C21 C22 115.0(3) . . ? N2 C21 H15 108.5 . . ? C22 C21 H15 108.5 . . ? N2 C21 H16 108.5 . . ? C22 C21 H16 108.5 . . ? H15 C21 H16 107.5 . . ? C23 C22 C27 117.2(3) . . ? C23 C22 C21 124.1(3) . . ? C27 C22 C21 118.7(3) . . ? C22 C23 C24 120.8(4) . . ? C22 C23 H21 119.6 . . ? C24 C23 H21 119.6 . . ? C25 C24 C23 120.5(5) . . ? C25 C24 H20 119.8 . . ? C23 C24 H20 119.8 . . ? C26 C25 C24 119.8(4) . . ? C26 C25 H19 120.1 . . ? C24 C25 H19 120.1 . . ? C25 C26 C27 120.1(5) . . ? C25 C26 H18 119.9 . . ? C27 C26 H18 119.9 . . ? C22 C27 C26 121.6(5) . . ? C22 C27 H17 119.2 . . ? C26 C27 H17 119.2 . . ? O4 C28 C3 105.2(2) . . ? O4 C28 H23 110.7 . . ? C3 C28 H23 110.7 . . ? O4 C28 H22 110.7 . . ? C3 C28 H22 110.7 . . ? H23 C28 H22 108.8 . . ? C2 C29 H26 109.5 . . ? C2 C29 H24 109.5 . . ? H26 C29 H24 109.5 . . ? C2 C29 H25 109.5 . . ? H26 C29 H25 109.5 . . ? H24 C29 H25 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O3 S1 N1 C6 38.1(3) . . . . ? O2 S1 N1 C6 166.4(2) . . . . ? C7 S1 N1 C6 -80.8(2) . . . . ? C28 O4 C2 O1 33.6(4) . . . . ? C28 O4 C2 C29 -85.9(4) . . . . ? C28 O4 C2 C1 149.1(4) . . . . ? C3 O1 C2 O4 -34.2(4) . . . . ? C3 O1 C2 C29 86.4(3) . . . . ? C3 O1 C2 C1 -150.0(3) . . . . ? C2 O1 C3 C4 143.4(3) . . . . ? C2 O1 C3 C28 22.1(3) . . . . ? O1 C3 C4 C5 139.3(2) . . . . ? C28 C3 C4 C5 -104.8(3) . . . . ? C3 C4 C5 C6 164.2(2) . . . . ? S1 N1 C6 N2 179.77(18) . . . . ? S1 N1 C6 C5 2.2(4) . . . . ? C21 N2 C6 N1 2.3(4) . . . . ? C14 N2 C6 N1 -179.8(2) . . . . ? C21 N2 C6 C5 -180.0(2) . . . . ? C14 N2 C6 C5 -2.1(4) . . . . ? C4 C5 C6 N1 -109.2(3) . . . . ? C4 C5 C6 N2 73.3(4) . . . . ? O3 S1 C7 C12 -2.4(2) . . . . ? O2 S1 C7 C12 -128.2(2) . . . . ? N1 S1 C7 C12 120.8(2) . . . . ? O3 S1 C7 C8 175.74(18) . . . . ? O2 S1 C7 C8 49.9(2) . . . . ? N1 S1 C7 C8 -61.1(2) . . . . ? C12 C7 C8 C9 1.2(4) . . . . ? S1 C7 C8 C9 -176.9(2) . . . . ? C7 C8 C9 C10 0.8(4) . . . . ? C8 C9 C10 C13 -1.7(4) . . . . ? C8 C9 C10 C11 178.8(3) . . . . ? C8 C7 C12 C13 -2.2(3) . . . . ? S1 C7 C12 C13 175.88(18) . . . . ? C7 C12 C13 C10 1.3(3) . . . . ? C9 C10 C13 C12 0.6(4) . . . . ? C11 C10 C13 C12 -179.9(2) . . . . ? C6 N2 C14 C15 -94.3(3) . . . . ? C21 N2 C14 C15 83.6(3) . . . . ? N2 C14 C15 C16 170.3(3) . . . . ? N2 C14 C15 C20 -11.1(4) . . . . ? C20 C15 C16 C17 0.9(5) . . . . ? C14 C15 C16 C17 179.6(3) . . . . ? C15 C16 C17 C18 -0.7(6) . . . . ? C16 C17 C18 C19 0.7(6) . . . . ? C17 C18 C19 C20 -0.8(6) . . . . ? C18 C19 C20 C15 1.0(6) . . . . ? C16 C15 C20 C19 -1.0(5) . . . . ? C14 C15 C20 C19 -179.7(3) . . . . ? C6 N2 C21 C22 -78.0(3) . . . . ? C14 N2 C21 C22 104.1(3) . . . . ? N2 C21 C22 C23 3.6(4) . . . . ? N2 C21 C22 C27 -178.0(3) . . . . ? C27 C22 C23 C24 0.7(5) . . . . ? C21 C22 C23 C24 179.2(3) . . . . ? C22 C23 C24 C25 -0.2(6) . . . . ? C23 C24 C25 C26 -0.3(7) . . . . ? C24 C25 C26 C27 0.2(7) . . . . ? C23 C22 C27 C26 -0.8(5) . . . . ? C21 C22 C27 C26 -179.4(3) . . . . ? C25 C26 C27 C22 0.4(6) . . . . ? C2 O4 C28 C3 -19.5(4) . . . . ? O1 C3 C28 O4 -1.8(4) . . . . ? C4 C3 C28 O4 -121.8(3) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 28.33 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.477 _refine_diff_density_min -0.328 _refine_diff_density_rms 0.066 _database_code_depnum_ccdc_archive 'CCDC 932111' ####################################################################### # # 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_tr1 #TrackingRef '19081_web_deposit_cif_file_1_DineshChauhan_1364820399.SRE- 71.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H18 N2 O3 S' _chemical_formula_sum 'C14 H18 N2 O3 S' _chemical_formula_weight 294.37 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 P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.2660(12) _cell_length_b 25.831(4) _cell_length_c 13.5551(19) _cell_angle_alpha 90.00 _cell_angle_beta 97.899(4) _cell_angle_gamma 90.00 _cell_volume 2866.8(7) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 1.58 _cell_measurement_theta_max 28.52 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.370 _exptl_crystal_size_mid 0.180 _exptl_crystal_size_min 0.083 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.364 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1248 _exptl_absorpt_coefficient_mu 0.235 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.951 _exptl_absorpt_correction_T_max 0.981 _exptl_absorpt_process_details 'multi-scan absorption correction' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 28718 _diffrn_reflns_av_R_equivalents 0.0422 _diffrn_reflns_av_sigmaI/netI 0.0387 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -31 _diffrn_reflns_limit_k_max 34 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.58 _diffrn_reflns_theta_max 28.52 _reflns_number_total 7203 _reflns_number_gt 5766 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0422P)^2^+1.4362P] 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 0.0003(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 7267 _refine_ls_number_parameters 364 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0543 _refine_ls_R_factor_gt 0.0395 _refine_ls_wR_factor_ref 0.1035 _refine_ls_wR_factor_gt 0.0953 _refine_ls_goodness_of_fit_ref 1.019 _refine_ls_restrained_S_all 1.019 _refine_ls_shift/su_max 0.044 _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 0.79608(5) -0.000561(15) 0.76648(3) 0.02393(10) Uani 1 1 d . . . S2 S 0.17164(5) 0.244657(14) 0.58360(3) 0.02236(10) Uani 1 1 d . . . O1 O 0.80196(17) -0.01925(5) 0.86720(10) 0.0395(3) Uani 1 1 d . . . O2 O 0.94278(14) -0.00558(5) 0.72067(11) 0.0397(3) Uani 1 1 d . . . O4 O 0.01445(17) 0.23221(5) 0.52841(10) 0.0376(3) Uani 1 1 d . . . O5 O 0.31298(17) 0.23160(5) 0.53696(10) 0.0368(3) Uani 1 1 d . . . N1 N 0.63751(15) -0.02225(5) 0.69542(10) 0.0237(3) Uani 1 1 d . . . O3 O 0.15918(14) -0.11268(5) 0.54461(9) 0.0299(3) Uani 1 1 d . . . N4 N 0.18661(17) 0.22382(5) 0.69667(10) 0.0232(3) Uani 1 1 d . . . C1 C 0.6583(3) 0.23017(7) 0.77278(16) 0.0434(5) Uani 1 1 d . . . H1A H 0.7403 0.2481 0.7423 0.065 Uiso 1 1 calc R . . H1B H 0.6625 0.2413 0.8407 0.065 Uiso 1 1 calc R . . H1C H 0.5525 0.2377 0.7371 0.065 Uiso 1 1 calc R . . C2 C 0.6891(2) 0.17253(6) 0.77012(12) 0.0263(3) Uani 1 1 d . . . C3 C 0.64342(19) 0.14019(7) 0.84376(12) 0.0264(3) Uani 1 1 d . . . H3 H 0.5930 0.1544 0.8948 0.032 Uiso 1 1 calc R . . C4 C 0.67161(18) 0.08723(6) 0.84264(12) 0.0232(3) Uani 1 1 d . . . H4 H 0.6399 0.0661 0.8921 0.028 Uiso 1 1 calc R . . C5 C 0.74776(17) 0.06618(6) 0.76663(11) 0.0196(3) Uani 1 1 d . . . C8 C 0.62279(18) -0.07195(6) 0.67224(11) 0.0204(3) Uani 1 1 d . . . N3 N 0.48918(16) -0.08648(5) 0.61081(10) 0.0252(3) Uani 1 1 d . . . C12 C 0.3728(2) -0.04795(7) 0.56374(15) 0.0342(4) Uani 1 1 d . . . H12A H 0.3787 -0.0466 0.4928 0.041 Uiso 1 1 calc R . . H12B H 0.4010 -0.0140 0.5915 0.041 Uiso 1 1 calc R . . C11 C 0.2012(2) -0.06180(7) 0.58074(15) 0.0367(4) Uani 1 1 d . . . H11A H 0.1931 -0.0601 0.6514 0.044 Uiso 1 1 calc R . . H11B H 0.1249 -0.0370 0.5468 0.044 Uiso 1 1 calc R . . C9 C 0.4431(2) -0.14009(6) 0.58296(14) 0.0298(4) Uani 1 1 d . . . H9A H 0.5135 -0.1640 0.6240 0.036 Uiso 1 1 calc R . . H9B H 0.4566 -0.1461 0.5139 0.036 Uiso 1 1 calc R . . C10 C 0.2667(2) -0.14931(7) 0.59731(14) 0.0331(4) Uani 1 1 d . . . H10A H 0.2347 -0.1839 0.5745 0.040 Uiso 1 1 calc R . . H10B H 0.2571 -0.1473 0.6677 0.040 Uiso 1 1 calc R . . C13 C 0.74851(19) -0.11116(6) 0.70985(13) 0.0254(3) Uani 1 1 d . . . H13 H 0.7719 -0.1159 0.7783 0.030 Uiso 1 1 calc R . . C14 C 0.8280(2) -0.13936(7) 0.65217(15) 0.0352(4) Uani 1 1 d . . . H14A H 0.8072 -0.1355 0.5834 0.042 Uiso 1 1 calc R . . H14B H 0.9052 -0.1633 0.6800 0.042 Uiso 1 1 calc R . . C6 C 0.79517(19) 0.09767(6) 0.69257(12) 0.0234(3) Uani 1 1 d . . . H6 H 0.8466 0.0834 0.6421 0.028 Uiso 1 1 calc R . . C7 C 0.7653(2) 0.15051(7) 0.69438(12) 0.0268(3) Uani 1 1 d . . . H7 H 0.7964 0.1715 0.6446 0.032 Uiso 1 1 calc R . . C15 C 0.1806(2) 0.47866(6) 0.62551(14) 0.0327(4) Uani 1 1 d . . . H15A H 0.2831 0.4902 0.6606 0.049 Uiso 1 1 calc R . . H15B H 0.0933 0.4903 0.6599 0.049 Uiso 1 1 calc R . . H15C H 0.1666 0.4926 0.5592 0.049 Uiso 1 1 calc R . . C16 C 0.17909(19) 0.42026(6) 0.62044(11) 0.0209(3) Uani 1 1 d . . . C17 C 0.32360(19) 0.39252(6) 0.62236(12) 0.0233(3) Uani 1 1 d . . . H17 H 0.4226 0.4102 0.6291 0.028 Uiso 1 1 calc R . . C18 C 0.32267(19) 0.33888(6) 0.61434(12) 0.0222(3) Uani 1 1 d . . . H18 H 0.4203 0.3209 0.6152 0.027 Uiso 1 1 calc R . . C19 C 0.17537(18) 0.31229(6) 0.60506(11) 0.0190(3) Uani 1 1 d . . . C22 C 0.19033(17) 0.17401(6) 0.71818(11) 0.0191(3) Uani 1 1 d . . . N5 N 0.20520(17) 0.16147(5) 0.81496(10) 0.0242(3) Uani 1 1 d . . . C26 C 0.2338(2) 0.20230(7) 0.89096(12) 0.0316(4) Uani 1 1 d . . . H26A H 0.2110 0.2358 0.8599 0.038 Uiso 1 1 calc R . . H26B H 0.3475 0.2018 0.9205 0.038 Uiso 1 1 calc R . . C25 C 0.1267(2) 0.19461(7) 0.97110(13) 0.0313(4) Uani 1 1 d . . . H25A H 0.1526 0.2206 1.0224 0.038 Uiso 1 1 calc R . . H25B H 0.0132 0.1989 0.9428 0.038 Uiso 1 1 calc R . . O6 O 0.14927(13) 0.14438(5) 1.01442(8) 0.0264(3) Uani 1 1 d . . . C21 C 0.03215(19) 0.39297(6) 0.61271(11) 0.0224(3) Uani 1 1 d . . . H21 H -0.0655 0.4109 0.6122 0.027 Uiso 1 1 calc R . . C20 C 0.02982(18) 0.33914(6) 0.60574(11) 0.0220(3) Uani 1 1 d . . . H20 H -0.0686 0.3213 0.6016 0.026 Uiso 1 1 calc R . . C27 C 0.17941(19) 0.13295(6) 0.64028(12) 0.0224(3) Uani 1 1 d . . . H27 H 0.0865 0.1321 0.5931 0.027 Uiso 1 1 calc R . . C28 C 0.2931(2) 0.09773(7) 0.63404(14) 0.0344(4) Uani 1 1 d . . . H28A H 0.3874 0.0975 0.6801 0.041 Uiso 1 1 calc R . . H28B H 0.2789 0.0731 0.5836 0.041 Uiso 1 1 calc R . . C23 C 0.2054(2) 0.10863(6) 0.85561(12) 0.0236(3) Uani 1 1 d . . . H23A H 0.3164 0.0984 0.8805 0.028 Uiso 1 1 calc R . . H23B H 0.1628 0.0847 0.8033 0.028 Uiso 1 1 calc R . . C24 C 0.10107(19) 0.10624(7) 0.93947(12) 0.0263(3) Uani 1 1 d . . . H24A H -0.0125 0.1117 0.9124 0.032 Uiso 1 1 calc R . . H24B H 0.1104 0.0721 0.9695 0.032 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 0.02072(18) 0.01827(19) 0.0304(2) -0.00099(15) -0.00505(14) -0.00140(15) S2 0.0339(2) 0.01465(17) 0.01761(18) 0.00065(14) 0.00038(14) -0.00134(15) O1 0.0519(8) 0.0274(6) 0.0333(7) 0.0073(5) -0.0148(6) -0.0044(6) O2 0.0214(6) 0.0291(7) 0.0685(10) -0.0101(6) 0.0061(6) 0.0009(5) O4 0.0490(8) 0.0212(6) 0.0360(7) 0.0014(5) -0.0175(6) -0.0073(6) O5 0.0574(8) 0.0223(6) 0.0353(7) -0.0013(5) 0.0226(6) 0.0024(6) N1 0.0220(6) 0.0184(6) 0.0287(7) -0.0025(5) -0.0040(5) -0.0018(5) O3 0.0275(6) 0.0312(7) 0.0296(6) 0.0001(5) -0.0016(5) -0.0055(5) N4 0.0341(7) 0.0160(6) 0.0190(6) 0.0017(5) 0.0013(5) -0.0005(5) C1 0.0554(12) 0.0236(9) 0.0488(12) -0.0048(8) -0.0010(10) 0.0055(9) C2 0.0281(8) 0.0197(8) 0.0287(9) -0.0050(6) -0.0045(6) -0.0002(6) C3 0.0248(8) 0.0308(9) 0.0234(8) -0.0089(7) 0.0025(6) 0.0001(7) C4 0.0220(7) 0.0277(8) 0.0197(7) 0.0003(6) 0.0021(6) -0.0053(6) C5 0.0170(6) 0.0187(7) 0.0216(7) -0.0027(6) -0.0028(5) -0.0035(6) C8 0.0211(7) 0.0189(7) 0.0212(7) -0.0006(6) 0.0032(5) -0.0018(6) N3 0.0269(7) 0.0161(6) 0.0301(7) -0.0013(5) -0.0050(5) -0.0018(5) C12 0.0345(9) 0.0190(8) 0.0436(11) 0.0010(7) -0.0145(8) -0.0021(7) C11 0.0326(9) 0.0345(10) 0.0400(10) -0.0099(8) -0.0054(8) 0.0060(8) C9 0.0322(9) 0.0187(8) 0.0362(10) -0.0067(7) -0.0033(7) -0.0037(7) C10 0.0348(9) 0.0283(9) 0.0339(10) 0.0057(7) -0.0034(7) -0.0087(7) C13 0.0271(8) 0.0200(8) 0.0284(8) 0.0013(6) 0.0012(6) -0.0003(6) C14 0.0364(9) 0.0269(9) 0.0431(11) 0.0020(8) 0.0086(8) 0.0060(8) C6 0.0258(7) 0.0251(8) 0.0196(7) -0.0028(6) 0.0037(6) -0.0035(6) C7 0.0318(8) 0.0254(8) 0.0226(8) 0.0026(6) 0.0016(6) -0.0048(7) C15 0.0390(10) 0.0170(8) 0.0412(10) -0.0015(7) 0.0023(8) -0.0004(7) C16 0.0270(7) 0.0168(7) 0.0184(7) -0.0004(6) 0.0017(6) -0.0008(6) C17 0.0217(7) 0.0211(8) 0.0270(8) 0.0001(6) 0.0033(6) -0.0041(6) C18 0.0215(7) 0.0211(8) 0.0237(8) 0.0009(6) 0.0023(6) 0.0023(6) C19 0.0261(7) 0.0150(7) 0.0154(7) 0.0014(5) 0.0010(5) -0.0005(6) C22 0.0184(7) 0.0177(7) 0.0206(7) 0.0005(6) 0.0009(5) -0.0008(6) N5 0.0372(7) 0.0147(6) 0.0197(7) 0.0012(5) 0.0011(5) -0.0026(6) C26 0.0557(11) 0.0193(8) 0.0188(8) -0.0023(6) 0.0014(7) -0.0056(8) C25 0.0383(9) 0.0277(9) 0.0266(9) -0.0032(7) -0.0002(7) 0.0066(7) O6 0.0258(6) 0.0309(6) 0.0223(6) 0.0023(5) 0.0025(4) -0.0009(5) C21 0.0218(7) 0.0227(8) 0.0226(8) -0.0005(6) 0.0022(6) 0.0031(6) C20 0.0205(7) 0.0231(8) 0.0222(8) 0.0006(6) 0.0019(6) -0.0037(6) C27 0.0275(8) 0.0177(7) 0.0212(8) 0.0002(6) 0.0005(6) -0.0024(6) C28 0.0449(10) 0.0267(9) 0.0306(9) -0.0060(7) 0.0013(7) 0.0084(8) C23 0.0296(8) 0.0169(7) 0.0238(8) 0.0033(6) 0.0021(6) 0.0002(6) C24 0.0246(8) 0.0273(8) 0.0265(8) 0.0032(7) 0.0020(6) -0.0048(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 O2 1.4421(13) . ? S1 O1 1.4426(14) . ? S1 N1 1.6164(13) . ? S1 C5 1.7698(16) . ? S2 O5 1.4427(13) . ? S2 O4 1.4436(13) . ? S2 N4 1.6131(13) . ? S2 C19 1.7707(15) . ? N1 C8 1.3234(19) . ? O3 C10 1.422(2) . ? O3 C11 1.429(2) . ? N4 C22 1.3186(19) . ? C1 C2 1.512(2) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C3 1.393(2) . ? C2 C7 1.397(2) . ? C3 C4 1.388(2) . ? C3 H3 0.9300 . ? C4 C5 1.390(2) . ? C4 H4 0.9300 . ? C5 C6 1.390(2) . ? C8 N3 1.3420(19) . ? C8 C13 1.490(2) . ? N3 C12 1.468(2) . ? N3 C9 1.472(2) . ? C12 C11 1.511(3) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C9 C10 1.516(2) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C13 C14 1.309(2) . ? C13 H13 0.9300 . ? C14 H14A 0.9300 . ? C14 H14B 0.9300 . ? C6 C7 1.388(2) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C15 C16 1.510(2) . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 C17 1.390(2) . ? C16 C21 1.396(2) . ? C17 C18 1.390(2) . ? C17 H17 0.9300 . ? C18 C19 1.389(2) . ? C18 H18 0.9300 . ? C19 C20 1.390(2) . ? C22 N5 1.340(2) . ? C22 C27 1.491(2) . ? N5 C26 1.471(2) . ? N5 C23 1.4718(19) . ? C26 C25 1.505(3) . ? C26 H26A 0.9700 . ? C26 H26B 0.9700 . ? C25 O6 1.426(2) . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? O6 C24 1.432(2) . ? C21 C20 1.394(2) . ? C21 H21 0.9300 . ? C20 H20 0.9300 . ? C27 C28 1.319(2) . ? C27 H27 0.9300 . ? C28 H28A 0.9300 . ? C28 H28B 0.9300 . ? C23 C24 1.519(2) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 S1 O1 117.16(9) . . ? O2 S1 N1 111.91(8) . . ? O1 S1 N1 111.53(8) . . ? O2 S1 C5 106.94(8) . . ? O1 S1 C5 107.65(8) . . ? N1 S1 C5 100.00(7) . . ? O5 S2 O4 116.51(9) . . ? O5 S2 N4 112.17(8) . . ? O4 S2 N4 111.35(8) . . ? O5 S2 C19 107.80(7) . . ? O4 S2 C19 107.40(7) . . ? N4 S2 C19 100.12(7) . . ? C8 N1 S1 121.22(11) . . ? C10 O3 C11 109.53(13) . . ? C22 N4 S2 122.14(11) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C3 C2 C7 118.45(15) . . ? C3 C2 C1 120.70(16) . . ? C7 C2 C1 120.85(17) . . ? C4 C3 C2 121.39(15) . . ? C4 C3 H3 119.3 . . ? C2 C3 H3 119.3 . . ? C3 C4 C5 119.17(15) . . ? C3 C4 H4 120.4 . . ? C5 C4 H4 120.4 . . ? C4 C5 C6 120.52(15) . . ? C4 C5 S1 120.48(12) . . ? C6 C5 S1 118.90(12) . . ? N1 C8 N3 117.36(14) . . ? N1 C8 C13 122.76(13) . . ? N3 C8 C13 119.87(14) . . ? C8 N3 C12 120.96(13) . . ? C8 N3 C9 125.74(13) . . ? C12 N3 C9 113.30(12) . . ? N3 C12 C11 110.25(15) . . ? N3 C12 H12A 109.6 . . ? C11 C12 H12A 109.6 . . ? N3 C12 H12B 109.6 . . ? C11 C12 H12B 109.6 . . ? H12A C12 H12B 108.1 . . ? O3 C11 C12 110.78(15) . . ? O3 C11 H11A 109.5 . . ? C12 C11 H11A 109.5 . . ? O3 C11 H11B 109.5 . . ? C12 C11 H11B 109.5 . . ? H11A C11 H11B 108.1 . . ? N3 C9 C10 109.53(14) . . ? N3 C9 H9A 109.8 . . ? C10 C9 H9A 109.8 . . ? N3 C9 H9B 109.8 . . ? C10 C9 H9B 109.8 . . ? H9A C9 H9B 108.2 . . ? O3 C10 C9 112.14(14) . . ? O3 C10 H10A 109.2 . . ? C9 C10 H10A 109.2 . . ? O3 C10 H10B 109.2 . . ? C9 C10 H10B 109.2 . . ? H10A C10 H10B 107.9 . . ? C14 C13 C8 123.87(16) . . ? C14 C13 H13 118.1 . . ? C8 C13 H13 118.1 . . ? C13 C14 H14A 120.0 . . ? C13 C14 H14B 120.0 . . ? H14A C14 H14B 120.0 . . ? C7 C6 C5 119.63(15) . . ? C7 C6 H6 120.2 . . ? C5 C6 H6 120.2 . . ? C6 C7 C2 120.83(15) . . ? C6 C7 H7 119.6 . . ? C2 C7 H7 119.6 . . ? C16 C15 H15A 109.5 . . ? C16 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C16 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C17 C16 C21 118.53(14) . . ? C17 C16 C15 120.81(14) . . ? C21 C16 C15 120.65(14) . . ? C18 C17 C16 121.13(14) . . ? C18 C17 H17 119.4 . . ? C16 C17 H17 119.4 . . ? C19 C18 C17 119.71(14) . . ? C19 C18 H18 120.1 . . ? C17 C18 H18 120.1 . . ? C18 C19 C20 120.11(14) . . ? C18 C19 S2 119.88(12) . . ? C20 C19 S2 119.86(11) . . ? N4 C22 N5 116.64(14) . . ? N4 C22 C27 122.71(14) . . ? N5 C22 C27 120.64(13) . . ? C22 N5 C26 119.77(13) . . ? C22 N5 C23 125.86(13) . . ? C26 N5 C23 114.27(13) . . ? N5 C26 C25 110.92(14) . . ? N5 C26 H26A 109.5 . . ? C25 C26 H26A 109.5 . . ? N5 C26 H26B 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 108.0 . . ? O6 C25 C26 111.15(14) . . ? O6 C25 H25A 109.4 . . ? C26 C25 H25A 109.4 . . ? O6 C25 H25B 109.4 . . ? C26 C25 H25B 109.4 . . ? H25A C25 H25B 108.0 . . ? C25 O6 C24 109.02(12) . . ? C20 C21 C16 120.85(14) . . ? C20 C21 H21 119.6 . . ? C16 C21 H21 119.6 . . ? C19 C20 C21 119.64(14) . . ? C19 C20 H20 120.2 . . ? C21 C20 H20 120.2 . . ? C28 C27 C22 124.19(15) . . ? C28 C27 H27 117.9 . . ? C22 C27 H27 117.9 . . ? C27 C28 H28A 120.0 . . ? C27 C28 H28B 120.0 . . ? H28A C28 H28B 120.0 . . ? N5 C23 C24 110.25(13) . . ? N5 C23 H23A 109.6 . . ? C24 C23 H23A 109.6 . . ? N5 C23 H23B 109.6 . . ? C24 C23 H23B 109.6 . . ? H23A C23 H23B 108.1 . . ? O6 C24 C23 111.82(13) . . ? O6 C24 H24A 109.3 . . ? C23 C24 H24A 109.3 . . ? O6 C24 H24B 109.3 . . ? C23 C24 H24B 109.3 . . ? H24A C24 H24B 107.9 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 S1 N1 C8 65.61(15) . . . . ? O1 S1 N1 C8 -67.84(15) . . . . ? C5 S1 N1 C8 178.55(13) . . . . ? O5 S2 N4 C22 -65.31(15) . . . . ? O4 S2 N4 C22 67.29(15) . . . . ? C19 S2 N4 C22 -179.39(13) . . . . ? C7 C2 C3 C4 -0.3(2) . . . . ? C1 C2 C3 C4 -179.66(16) . . . . ? C2 C3 C4 C5 0.3(2) . . . . ? C3 C4 C5 C6 0.0(2) . . . . ? C3 C4 C5 S1 176.44(11) . . . . ? O2 S1 C5 C4 -148.09(12) . . . . ? O1 S1 C5 C4 -21.39(14) . . . . ? N1 S1 C5 C4 95.17(13) . . . . ? O2 S1 C5 C6 28.42(14) . . . . ? O1 S1 C5 C6 155.13(12) . . . . ? N1 S1 C5 C6 -88.31(13) . . . . ? S1 N1 C8 N3 -178.37(12) . . . . ? S1 N1 C8 C13 0.5(2) . . . . ? N1 C8 N3 C12 5.9(2) . . . . ? C13 C8 N3 C12 -173.02(16) . . . . ? N1 C8 N3 C9 -174.44(16) . . . . ? C13 C8 N3 C9 6.7(2) . . . . ? C8 N3 C12 C11 -128.73(16) . . . . ? C9 N3 C12 C11 51.6(2) . . . . ? C10 O3 C11 C12 61.57(19) . . . . ? N3 C12 C11 O3 -56.5(2) . . . . ? C8 N3 C9 C10 130.13(17) . . . . ? C12 N3 C9 C10 -50.2(2) . . . . ? C11 O3 C10 C9 -61.29(19) . . . . ? N3 C9 C10 O3 54.93(19) . . . . ? N1 C8 C13 C14 -119.38(19) . . . . ? N3 C8 C13 C14 59.4(2) . . . . ? C4 C5 C6 C7 -0.4(2) . . . . ? S1 C5 C6 C7 -176.87(12) . . . . ? C5 C6 C7 C2 0.4(2) . . . . ? C3 C2 C7 C6 -0.1(2) . . . . ? C1 C2 C7 C6 179.28(16) . . . . ? C21 C16 C17 C18 1.6(2) . . . . ? C15 C16 C17 C18 -177.80(15) . . . . ? C16 C17 C18 C19 -0.5(2) . . . . ? C17 C18 C19 C20 -1.2(2) . . . . ? C17 C18 C19 S2 174.33(12) . . . . ? O5 S2 C19 C18 -24.72(14) . . . . ? O4 S2 C19 C18 -151.01(13) . . . . ? N4 S2 C19 C18 92.66(13) . . . . ? O5 S2 C19 C20 150.86(12) . . . . ? O4 S2 C19 C20 24.57(15) . . . . ? N4 S2 C19 C20 -91.76(13) . . . . ? S2 N4 C22 N5 179.15(11) . . . . ? S2 N4 C22 C27 -0.6(2) . . . . ? N4 C22 N5 C26 -6.4(2) . . . . ? C27 C22 N5 C26 173.33(15) . . . . ? N4 C22 N5 C23 177.43(14) . . . . ? C27 C22 N5 C23 -2.8(2) . . . . ? C22 N5 C26 C25 135.35(15) . . . . ? C23 N5 C26 C25 -48.09(19) . . . . ? N5 C26 C25 O6 55.49(19) . . . . ? C26 C25 O6 C24 -62.66(17) . . . . ? C17 C16 C21 C20 -0.8(2) . . . . ? C15 C16 C21 C20 178.53(15) . . . . ? C18 C19 C20 C21 1.9(2) . . . . ? S2 C19 C20 C21 -173.62(12) . . . . ? C16 C21 C20 C19 -0.9(2) . . . . ? N4 C22 C27 C28 120.22(19) . . . . ? N5 C22 C27 C28 -59.5(2) . . . . ? C22 N5 C23 C24 -136.77(16) . . . . ? C26 N5 C23 C24 46.92(18) . . . . ? C25 O6 C24 C23 62.09(16) . . . . ? N5 C23 C24 O6 -53.74(17) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 28.52 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.364 _refine_diff_density_min -0.307 _refine_diff_density_rms 0.052 _database_code_depnum_ccdc_archive 'CCDC 932112' ####################################################################### # # 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_dinesh #TrackingRef 'web_deposit_cif_file_0_DineshChauhan_1365517050.DINESH.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H26 N2 O3 S' _chemical_formula_sum 'C21 H26 N2 O3 S' _chemical_formula_weight 386.51 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' 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 Triclinic _symmetry_space_group_name_H-M 'P-1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.0234(13) _cell_length_b 9.3284(13) _cell_length_c 12.4285(18) _cell_angle_alpha 76.805(2) _cell_angle_beta 86.796(2) _cell_angle_gamma 74.132(2) _cell_volume 979.7(2) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 9597 _cell_measurement_theta_min 2.33 _cell_measurement_theta_max 28.38 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.310 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 412 _exptl_absorpt_coefficient_mu 0.189 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.953 _exptl_absorpt_correction_T_max 0.991 _exptl_absorpt_process_details 'multi-scan absorption correction' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 18623 _diffrn_reflns_av_R_equivalents 0.0203 _diffrn_reflns_av_sigmaI/netI 0.0187 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.33 _diffrn_reflns_theta_max 28.43 _reflns_number_total 4933 _reflns_number_gt 4400 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4916 _refine_ls_number_parameters 248 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0388 _refine_ls_R_factor_gt 0.0346 _refine_ls_wR_factor_ref 0.1406 _refine_ls_wR_factor_gt 0.1333 _refine_ls_goodness_of_fit_ref 1.188 _refine_ls_restrained_S_all 1.188 _refine_ls_shift/su_max 0.002 _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 1.01770(3) 0.12680(3) 0.27068(2) 0.02449(12) Uani 1 1 d . . . O1 O 0.37532(10) 0.33144(10) -0.22648(7) 0.0331(2) Uani 1 1 d . . . O2 O 1.02840(10) 0.20543(9) 0.15721(7) 0.0320(2) Uani 1 1 d . . . O3 O 0.87625(10) 0.18058(10) 0.32747(8) 0.0345(2) Uani 1 1 d . . . N2 N 1.09692(11) -0.28413(10) 0.24171(8) 0.0246(2) Uani 1 1 d . . . N1 N 1.06241(11) -0.05640(10) 0.28983(8) 0.0262(2) Uani 1 1 d . . . C5 C 1.16871(12) 0.14982(11) 0.34459(9) 0.0234(2) Uani 1 1 d . . . C11 C 0.67284(12) 0.10777(12) 0.04157(9) 0.0237(2) Uani 1 1 d . . . C8 C 1.02511(12) -0.13397(12) 0.22376(9) 0.0228(2) Uani 1 1 d . . . C10 C 0.78167(13) 0.03650(12) 0.13303(10) 0.0254(2) Uani 1 1 d . . . H10 H 0.7573 0.0690 0.1988 0.031 Uiso 1 1 calc R . . C12 C 0.67322(13) 0.04694(12) -0.05223(10) 0.0257(2) Uani 1 1 d . . . H12 H 0.7430 -0.0459 -0.0560 0.031 Uiso 1 1 calc R . . C13 C 0.57239(13) 0.12232(13) -0.13810(9) 0.0267(2) Uani 1 1 d . . . H13 H 0.5729 0.0792 -0.1986 0.032 Uiso 1 1 calc R . . C16 C 0.56465(13) 0.24670(13) 0.04402(10) 0.0265(2) Uani 1 1 d . . . H16 H 0.5599 0.2872 0.1063 0.032 Uiso 1 1 calc R . . C6 C 1.16025(14) 0.13069(13) 0.45912(10) 0.0284(2) Uani 1 1 d . . . H6 H 1.0772 0.1028 0.4973 0.034 Uiso 1 1 calc R . . C7 C 1.27711(15) 0.15374(14) 0.51540(10) 0.0315(3) Uani 1 1 d . . . H7 H 1.2710 0.1417 0.5917 0.038 Uiso 1 1 calc R . . C14 C 0.46833(12) 0.26403(12) -0.13546(9) 0.0248(2) Uani 1 1 d . . . C3 C 1.41080(14) 0.21006(13) 0.34607(10) 0.0294(3) Uani 1 1 d . . . H3 H 1.4954 0.2348 0.3081 0.035 Uiso 1 1 calc R . . C2 C 1.40348(14) 0.19455(13) 0.46045(10) 0.0288(3) Uani 1 1 d . . . C9 C 0.91427(12) -0.07217(12) 0.13069(9) 0.0251(2) Uani 1 1 d . . . H9 H 0.9374 -0.1104 0.0671 0.030 Uiso 1 1 calc R . . C15 C 0.46396(13) 0.32620(13) -0.04345(10) 0.0276(2) Uani 1 1 d . . . H15 H 0.3947 0.4196 -0.0405 0.033 Uiso 1 1 calc R . . C4 C 1.29393(14) 0.18928(12) 0.28788(9) 0.0272(2) Uani 1 1 d . . . H4 H 1.2996 0.2017 0.2115 0.033 Uiso 1 1 calc R . . C1 C 1.52769(16) 0.22200(16) 0.52182(12) 0.0388(3) Uani 1 1 d . . . H1A H 1.4873 0.3129 0.5496 0.058 Uiso 1 1 calc R . . H1B H 1.6116 0.2343 0.4728 0.058 Uiso 1 1 calc R . . H1C H 1.5638 0.1364 0.5824 0.058 Uiso 1 1 calc R . . C17 C 0.30233(14) 0.49168(14) -0.24164(11) 0.0343(3) Uani 1 1 d . . . H17A H 0.2339 0.5094 -0.1812 0.051 Uiso 1 1 calc R . . H17B H 0.2448 0.5272 -0.3097 0.051 Uiso 1 1 calc R . . H17C H 0.3793 0.5459 -0.2442 0.051 Uiso 1 1 calc R . . C18 C 1.22371(13) -0.35354(13) 0.32217(10) 0.0268(2) Uani 1 1 d . . . H18A H 1.2768 -0.2775 0.3264 0.032 Uiso 1 1 calc R . . H18B H 1.2968 -0.4360 0.2964 0.032 Uiso 1 1 calc R . . C19 C 1.17027(17) -0.41554(16) 0.43627(11) 0.0400(3) Uani 1 1 d . . . H19A H 1.1045 -0.3331 0.4649 0.060 Uiso 1 1 calc R . . H19B H 1.2580 -0.4648 0.4842 0.060 Uiso 1 1 calc R . . H19C H 1.1143 -0.4882 0.4323 0.060 Uiso 1 1 calc R . . C20 C 1.04560(13) -0.39043(13) 0.19116(10) 0.0288(3) Uani 1 1 d . . . H20A H 0.9401 -0.3437 0.1656 0.035 Uiso 1 1 calc R . . H20B H 1.0468 -0.4823 0.2470 0.035 Uiso 1 1 calc R . . C21 C 1.14456(16) -0.43439(15) 0.09484(11) 0.0362(3) Uani 1 1 d . . . H21A H 1.1280 -0.3479 0.0334 0.054 Uiso 1 1 calc R . . H21B H 1.1171 -0.5167 0.0738 0.054 Uiso 1 1 calc R . . H21C H 1.2512 -0.4664 0.1164 0.054 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 0.02770(17) 0.01644(17) 0.02625(18) -0.00272(12) -0.00204(11) -0.00207(11) O1 0.0370(5) 0.0281(4) 0.0300(5) -0.0055(4) -0.0092(4) -0.0006(4) O2 0.0425(5) 0.0229(4) 0.0275(5) 0.0028(3) -0.0083(4) -0.0090(4) O3 0.0294(4) 0.0292(4) 0.0414(5) -0.0112(4) 0.0013(4) 0.0004(3) N2 0.0244(4) 0.0179(4) 0.0299(5) -0.0033(4) -0.0021(4) -0.0043(3) N1 0.0315(5) 0.0176(4) 0.0266(5) -0.0023(4) -0.0027(4) -0.0037(4) C5 0.0290(5) 0.0149(5) 0.0236(5) -0.0033(4) -0.0010(4) -0.0019(4) C11 0.0224(5) 0.0220(5) 0.0255(5) -0.0030(4) 0.0010(4) -0.0061(4) C8 0.0217(5) 0.0190(5) 0.0250(5) -0.0015(4) 0.0029(4) -0.0042(4) C10 0.0253(5) 0.0247(5) 0.0253(5) -0.0032(4) 0.0000(4) -0.0067(4) C12 0.0260(5) 0.0212(5) 0.0282(6) -0.0057(4) 0.0022(4) -0.0038(4) C13 0.0305(5) 0.0249(5) 0.0256(6) -0.0084(4) 0.0012(4) -0.0069(4) C16 0.0268(5) 0.0275(6) 0.0258(6) -0.0101(4) 0.0014(4) -0.0049(4) C6 0.0329(6) 0.0252(5) 0.0249(6) -0.0052(4) 0.0034(4) -0.0054(4) C7 0.0405(6) 0.0295(6) 0.0225(6) -0.0068(5) 0.0004(5) -0.0055(5) C14 0.0248(5) 0.0248(5) 0.0238(5) -0.0036(4) -0.0002(4) -0.0064(4) C3 0.0335(6) 0.0257(6) 0.0305(6) -0.0067(5) 0.0024(5) -0.0103(5) C2 0.0339(6) 0.0206(5) 0.0299(6) -0.0068(4) -0.0046(5) -0.0024(4) C9 0.0263(5) 0.0213(5) 0.0271(6) -0.0036(4) -0.0013(4) -0.0064(4) C15 0.0260(5) 0.0246(5) 0.0304(6) -0.0085(4) 0.0004(4) -0.0017(4) C4 0.0354(6) 0.0223(5) 0.0227(5) -0.0036(4) 0.0002(4) -0.0069(4) C1 0.0416(7) 0.0365(7) 0.0395(7) -0.0118(6) -0.0100(6) -0.0077(6) C17 0.0332(6) 0.0271(6) 0.0388(7) -0.0013(5) -0.0070(5) -0.0052(5) C18 0.0247(5) 0.0199(5) 0.0319(6) -0.0023(4) -0.0029(4) -0.0017(4) C19 0.0454(7) 0.0326(6) 0.0320(7) 0.0012(5) 0.0021(5) -0.0013(6) C20 0.0283(5) 0.0193(5) 0.0394(7) -0.0049(5) -0.0011(5) -0.0086(4) C21 0.0423(7) 0.0315(6) 0.0366(7) -0.0115(5) -0.0018(5) -0.0090(5) _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 1.4447(9) . ? S1 O3 1.4457(9) . ? S1 N1 1.6087(10) . ? S1 C5 1.7711(12) . ? O1 C14 1.3683(14) . ? O1 C17 1.4320(14) . ? N2 C8 1.3450(13) . ? N2 C18 1.4681(14) . ? N2 C20 1.4699(14) . ? N1 C8 1.3216(15) . ? C5 C4 1.3889(16) . ? C5 C6 1.3939(16) . ? C11 C16 1.3987(14) . ? C11 C12 1.4077(15) . ? C11 C10 1.4565(15) . ? C8 C9 1.4766(15) . ? C10 C9 1.3440(15) . ? C12 C13 1.3702(16) . ? C13 C14 1.4028(14) . ? C16 C15 1.3897(16) . ? C6 C7 1.3865(17) . ? C7 C2 1.3940(19) . ? C14 C15 1.3895(15) . ? C3 C4 1.3907(16) . ? C3 C2 1.3953(17) . ? C2 C1 1.4983(17) . ? C18 C19 1.5099(18) . ? C20 C21 1.5175(17) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 S1 O3 116.52(5) . . ? O2 S1 N1 114.26(5) . . ? O3 S1 N1 110.16(5) . . ? O2 S1 C5 106.93(5) . . ? O3 S1 C5 106.87(5) . . ? N1 S1 C5 100.50(5) . . ? C14 O1 C17 116.92(9) . . ? C8 N2 C18 120.97(9) . . ? C8 N2 C20 122.85(9) . . ? C18 N2 C20 115.94(9) . . ? C8 N1 S1 125.71(8) . . ? C4 C5 C6 120.30(11) . . ? C4 C5 S1 119.78(9) . . ? C6 C5 S1 119.91(9) . . ? C16 C11 C12 117.42(10) . . ? C16 C11 C10 119.04(10) . . ? C12 C11 C10 123.50(10) . . ? N1 C8 N2 116.93(10) . . ? N1 C8 C9 126.65(10) . . ? N2 C8 C9 116.42(10) . . ? C9 C10 C11 125.69(10) . . ? C13 C12 C11 121.02(10) . . ? C12 C13 C14 120.55(10) . . ? C15 C16 C11 122.22(10) . . ? C7 C6 C5 119.21(11) . . ? C6 C7 C2 121.68(11) . . ? O1 C14 C15 124.34(10) . . ? O1 C14 C13 115.90(9) . . ? C15 C14 C13 119.76(10) . . ? C4 C3 C2 121.21(11) . . ? C7 C2 C3 118.02(11) . . ? C7 C2 C1 121.25(11) . . ? C3 C2 C1 120.73(12) . . ? C10 C9 C8 123.44(10) . . ? C16 C15 C14 118.97(10) . . ? C5 C4 C3 119.56(11) . . ? N2 C18 C19 113.04(10) . . ? N2 C20 C21 113.36(10) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 28.43 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.333 _refine_diff_density_min -0.368 _refine_diff_density_rms 0.046 _database_code_depnum_ccdc_archive 'CCDC 933156'