data_sharp21 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23.50 H21 N2 O4 S' _chemical_formula_weight 427.48 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 21.68(5) _cell_length_b 5.975(14) _cell_length_c 31.44(7) _cell_angle_alpha 90.00 _cell_angle_beta 91.72(6) _cell_angle_gamma 90.00 _cell_volume 4070(16) _cell_formula_units_Z 8 _cell_measurement_temperature 94(2) _cell_measurement_reflns_used 1455 _cell_measurement_theta_min 3.25 _cell_measurement_theta_max 18.56 _exptl_crystal_description Needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_diffrn 1.395 _exptl_crystal_F_000 1792 _exptl_absorpt_coefficient_mu 0.194 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9180 _exptl_absorpt_correction_T_max 0.9904 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_reflns_number 20923 _diffrn_reflns_av_R_equivalents 0.0999 _diffrn_reflns_av_sigmaI/netI 0.0974 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -37 _diffrn_reflns_limit_l_max 38 _diffrn_reflns_theta_min 1.30 _diffrn_reflns_theta_max 25.74 _reflns_number_total 3759 _reflns_number_gt 1922 _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 ; Squeeze was used to determine that there were four molecules of ethyl acetate in the unit cell that were too disordered to be refine and were thus treated as diffuse electron density. 136 electrons, 34 each, were found in four voids with two fold symmetry. Since ethyl acetate does not have two fold symmetry these could not be refined. Their mass was added to the molecular formula. 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^)+(0.0884P)^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 0.0013(3) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 3759 _refine_ls_number_parameters 255 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1507 _refine_ls_R_factor_gt 0.0745 _refine_ls_wR_factor_ref 0.2027 _refine_ls_wR_factor_gt 0.1753 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.44587(19) 0.1923(8) 0.13397(14) 0.0529(11) Uani 1 1 d . . . C2 C 0.43624(19) 0.4730(7) 0.18052(12) 0.0494(11) Uani 1 1 d . . . C3 C 0.49560(19) 0.4413(7) 0.17634(12) 0.0538(11) Uani 1 1 d . . . H3 H 0.5277 0.5239 0.1902 0.065 Uiso 1 1 calc R . . C4 C 0.40658(19) 0.6320(8) 0.20862(12) 0.0530(11) Uani 1 1 d . . . C5 C 0.4344(2) 0.8322(8) 0.21715(14) 0.0601(12) Uani 1 1 d . . . H5 H 0.4717 0.8703 0.2037 0.072 Uiso 1 1 calc R . . C6 C 0.4090(2) 0.9774(9) 0.24492(15) 0.0717(14) Uani 1 1 d . . . H6 H 0.4286 1.1165 0.2508 0.086 Uiso 1 1 calc R . . C7 C 0.3561(3) 0.9255(10) 0.26413(15) 0.0791(16) Uani 1 1 d . . . H7 H 0.3393 1.0268 0.2840 0.095 Uiso 1 1 calc R . . C8 C 0.3268(2) 0.7307(10) 0.25531(15) 0.0845(17) Uani 1 1 d . . . H8 H 0.2885 0.6975 0.2679 0.101 Uiso 1 1 calc R . . C9 C 0.3527(2) 0.5820(9) 0.22813(14) 0.0687(14) Uani 1 1 d . . . H9 H 0.3331 0.4422 0.2227 0.082 Uiso 1 1 calc R . . C10 C 0.34115(18) 0.3096(8) 0.14530(13) 0.0527(11) Uani 1 1 d . . . C11 C 0.3109(2) 0.4908(9) 0.13021(14) 0.0638(13) Uani 1 1 d . . . H11 H 0.3321 0.6249 0.1237 0.077 Uiso 1 1 calc R . . C12 C 0.2470(2) 0.4740(11) 0.12454(18) 0.0859(18) Uani 1 1 d . . . H12 H 0.2240 0.5994 0.1144 0.103 Uiso 1 1 calc R . . C13 C 0.2175(3) 0.2804(12) 0.1334(2) 0.096(2) Uani 1 1 d . . . H13 H 0.1739 0.2724 0.1297 0.115 Uiso 1 1 calc R . . C14 C 0.2488(2) 0.0998(11) 0.1473(2) 0.0932(19) Uani 1 1 d . . . H14 H 0.2277 -0.0359 0.1528 0.112 Uiso 1 1 calc R . . C15 C 0.3121(2) 0.1128(9) 0.15360(15) 0.0663(13) Uani 1 1 d . . . H15 H 0.3349 -0.0134 0.1635 0.080 Uiso 1 1 calc R . . C16 C 0.57298(18) 0.2487(8) 0.08005(14) 0.0544(12) Uani 1 1 d . . . C17 C 0.5895(3) 0.4606(9) 0.07013(17) 0.0795(15) Uani 1 1 d . . . H17 H 0.5988 0.5653 0.0921 0.095 Uiso 1 1 calc R . . C18 C 0.5927(3) 0.5229(9) 0.02907(19) 0.0927(18) Uani 1 1 d . . . H18 H 0.6041 0.6723 0.0226 0.111 Uiso 1 1 calc R . . C19 C 0.5801(2) 0.3771(10) -0.00363(16) 0.0699(14) Uani 1 1 d . . . C20 C 0.5647(2) 0.1667(9) 0.00757(16) 0.0747(14) Uani 1 1 d . . . H20 H 0.5568 0.0597 -0.0143 0.090 Uiso 1 1 calc R . . C21 C 0.5601(2) 0.1005(9) 0.04920(16) 0.0708(14) Uani 1 1 d . . . H21 H 0.5479 -0.0477 0.0559 0.085 Uiso 1 1 calc R . . C22 C 0.5816(3) 0.4493(10) -0.04877(15) 0.0954(19) Uani 1 1 d . . . H22A H 0.5742 0.3198 -0.0674 0.143 Uiso 1 1 calc R . . H22B H 0.6221 0.5139 -0.0544 0.143 Uiso 1 1 calc R . . H22C H 0.5495 0.5618 -0.0543 0.143 Uiso 1 1 calc R . . N1 N 0.50320(14) 0.2672(6) 0.14827(10) 0.0547(10) Uani 1 1 d . . . N2 N 0.40518(14) 0.3202(6) 0.15416(10) 0.0495(9) Uani 1 1 d . . . O1 O 0.61370(12) 0.2893(5) 0.15679(9) 0.0662(9) Uani 1 1 d . . . O2 O 0.56676(13) -0.0648(5) 0.13451(9) 0.0636(9) Uani 1 1 d . . . O3 O 0.43572(12) 0.0489(6) 0.10777(10) 0.0660(9) Uani 1 1 d . . . S1 S 0.56962(5) 0.1689(2) 0.13228(4) 0.0579(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.046(3) 0.043(3) 0.070(3) -0.009(2) -0.001(2) -0.002(2) C2 0.047(2) 0.046(3) 0.055(2) -0.004(2) 0.004(2) -0.008(2) C3 0.049(3) 0.057(3) 0.055(3) -0.008(2) 0.001(2) -0.008(2) C4 0.050(2) 0.053(3) 0.056(2) -0.009(2) 0.002(2) 0.002(2) C5 0.061(3) 0.054(3) 0.066(3) -0.009(3) -0.003(2) -0.003(3) C6 0.083(4) 0.058(4) 0.073(3) -0.016(3) -0.011(3) -0.002(3) C7 0.082(4) 0.090(5) 0.066(3) -0.029(3) 0.010(3) 0.005(3) C8 0.077(3) 0.099(5) 0.079(3) -0.029(3) 0.024(3) -0.009(3) C9 0.061(3) 0.072(4) 0.073(3) -0.019(3) 0.013(2) -0.008(3) C10 0.040(2) 0.053(3) 0.066(3) -0.016(2) 0.009(2) 0.000(2) C11 0.058(3) 0.059(3) 0.074(3) -0.016(3) 0.003(2) 0.008(3) C12 0.061(3) 0.087(5) 0.109(4) -0.035(4) -0.020(3) 0.029(3) C13 0.049(3) 0.086(5) 0.152(5) -0.055(4) -0.002(3) -0.002(4) C14 0.059(3) 0.074(4) 0.148(5) -0.043(4) 0.023(3) -0.014(3) C15 0.048(3) 0.063(4) 0.087(3) -0.019(3) 0.002(2) 0.004(3) C16 0.048(2) 0.048(3) 0.068(3) -0.003(2) 0.009(2) 0.006(2) C17 0.104(4) 0.060(4) 0.075(4) -0.009(3) 0.006(3) -0.002(3) C18 0.145(5) 0.046(4) 0.088(4) 0.003(3) 0.024(4) -0.004(3) C19 0.066(3) 0.067(4) 0.077(3) 0.004(3) 0.011(3) 0.013(3) C20 0.086(4) 0.058(4) 0.080(4) -0.015(3) 0.005(3) -0.006(3) C21 0.079(3) 0.059(4) 0.076(3) -0.001(3) 0.014(3) -0.009(3) C22 0.112(4) 0.112(5) 0.063(3) 0.014(3) 0.015(3) 0.017(4) N1 0.0398(19) 0.061(3) 0.064(2) -0.0119(19) 0.0001(16) -0.0019(18) N2 0.0391(19) 0.045(2) 0.064(2) -0.0109(18) 0.0046(16) 0.0037(17) O1 0.0425(16) 0.077(2) 0.0787(19) -0.0019(17) -0.0075(15) -0.0008(16) O2 0.0597(19) 0.045(2) 0.086(2) 0.0069(16) 0.0035(16) 0.0098(15) O3 0.0471(17) 0.059(2) 0.092(2) -0.0224(18) -0.0014(16) 0.0009(16) S1 0.0442(6) 0.0573(9) 0.0722(8) 0.0024(6) 0.0044(5) 0.0072(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O3 1.204(5) . ? C1 N2 1.341(5) . ? C1 N1 1.383(6) . ? C2 C3 1.312(6) . ? C2 N2 1.393(5) . ? C2 C4 1.460(6) . ? C3 N1 1.377(5) . ? C4 C5 1.363(6) . ? C4 C9 1.369(6) . ? C5 C6 1.359(6) . ? C6 C7 1.348(7) . ? C7 C8 1.351(7) . ? C8 C9 1.365(7) . ? C10 C11 1.345(6) . ? C10 C15 1.363(7) . ? C10 N2 1.409(6) . ? C11 C12 1.393(8) . ? C12 C13 1.355(8) . ? C13 C14 1.341(8) . ? C14 C15 1.381(7) . ? C16 C21 1.337(6) . ? C16 C17 1.354(7) . ? C16 S1 1.713(6) . ? C17 C18 1.347(7) . ? C18 C19 1.369(7) . ? C19 C20 1.350(7) . ? C19 C22 1.484(7) . ? C20 C21 1.373(7) . ? N1 S1 1.648(5) . ? O1 S1 1.407(4) . ? O2 S1 1.400(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 C1 N2 128.3(4) . . ? O3 C1 N1 126.6(4) . . ? N2 C1 N1 105.0(4) . . ? C3 C2 N2 107.7(4) . . ? C3 C2 C4 127.3(4) . . ? N2 C2 C4 124.9(4) . . ? C2 C3 N1 108.1(4) . . ? C5 C4 C9 118.9(4) . . ? C5 C4 C2 119.3(4) . . ? C9 C4 C2 121.8(4) . . ? C6 C5 C4 120.0(5) . . ? C7 C6 C5 120.6(5) . . ? C6 C7 C8 120.5(5) . . ? C7 C8 C9 119.3(5) . . ? C8 C9 C4 120.7(5) . . ? C11 C10 C15 122.5(4) . . ? C11 C10 N2 120.1(4) . . ? C15 C10 N2 117.4(4) . . ? C10 C11 C12 117.4(5) . . ? C13 C12 C11 120.5(6) . . ? C14 C13 C12 121.1(5) . . ? C13 C14 C15 119.5(6) . . ? C10 C15 C14 119.0(5) . . ? C21 C16 C17 120.2(5) . . ? C21 C16 S1 119.8(4) . . ? C17 C16 S1 120.0(4) . . ? C18 C17 C16 120.0(5) . . ? C17 C18 C19 121.9(5) . . ? C20 C19 C18 116.2(5) . . ? C20 C19 C22 122.2(5) . . ? C18 C19 C22 121.6(5) . . ? C19 C20 C21 122.8(5) . . ? C16 C21 C20 118.7(5) . . ? C3 N1 C1 109.2(4) . . ? C3 N1 S1 126.0(3) . . ? C1 N1 S1 124.8(3) . . ? C1 N2 C2 110.0(4) . . ? C1 N2 C10 122.6(4) . . ? C2 N2 C10 127.1(3) . . ? O2 S1 O1 120.9(2) . . ? O2 S1 N1 107.46(19) . . ? O1 S1 N1 103.6(2) . . ? O2 S1 C16 109.2(2) . . ? O1 S1 C16 109.6(2) . . ? N1 S1 C16 104.8(2) . . ? _diffrn_measured_fraction_theta_max 0.963 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.206 _refine_diff_density_min -0.241 _refine_diff_density_rms 0.056