data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'J. Clayden' _publ_contact_author_email J.P.CLAYDEN@MAN.AC.UK _publ_section_title ; Relaying stereochemistry through aromatic ureas: 1,9 and 1,15 remote stereocontrol ; loop_ _publ_author_name 'J. Clayden' 'Lyn Jones' 'Mark Pickworth' # Attachment 's22661.cif' data_s2266 _database_code_depnum_ccdc_archive 'CCDC 703570' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H24 N2 O3 S' _chemical_formula_weight 372.47 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 Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 9.9463(5) _cell_length_b 13.5838(7) _cell_length_c 14.0922(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1903.98(17) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9058 _cell_measurement_theta_min 2.51 _cell_measurement_theta_max 26.38 _exptl_crystal_description prismatic _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.299 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 792 _exptl_absorpt_coefficient_mu 0.192 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9359 _exptl_absorpt_correction_T_max 0.9626 _exptl_absorpt_process_details ? _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15222 _diffrn_reflns_av_R_equivalents 0.0366 _diffrn_reflns_av_sigmaI/netI 0.0279 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.08 _diffrn_reflns_theta_max 26.38 _reflns_number_total 3902 _reflns_number_gt 3755 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0479P)^2^+0.1450P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.01(5) _refine_ls_number_reflns 3902 _refine_ls_number_parameters 240 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0293 _refine_ls_R_factor_gt 0.0281 _refine_ls_wR_factor_ref 0.0718 _refine_ls_wR_factor_gt 0.0713 _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_restrained_S_all 1.000 _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 0.92457(3) 0.90961(2) 0.32067(2) 0.01786(9) Uani 1 1 d . . . O1 O 0.94174(12) 0.98271(8) 0.24152(7) 0.0284(3) Uani 1 1 d . . . O2 O 0.73168(10) 0.81424(8) 0.53128(8) 0.0250(2) Uani 1 1 d . . . O3 O 0.92823(16) 0.93281(8) 0.78882(8) 0.0403(3) Uani 1 1 d . . . N1 N 0.95270(11) 0.85382(8) 0.53849(8) 0.0164(2) Uani 1 1 d . . . N2 N 0.78812(12) 0.97604(9) 0.52056(8) 0.0172(2) Uani 1 1 d . . . C1 C 1.06204(14) 0.93481(10) 0.40133(10) 0.0165(3) Uani 1 1 d . . . C2 C 1.16861(16) 0.98921(11) 0.36538(11) 0.0236(3) Uani 1 1 d . . . H2 H 1.1679 1.0092 0.3008 0.028 Uiso 1 1 calc R . . C3 C 1.27631(16) 1.01469(11) 0.42310(12) 0.0271(4) Uani 1 1 d . . . H3 H 1.3498 1.0509 0.3979 0.032 Uiso 1 1 calc R . . C4 C 1.27583(15) 0.98693(12) 0.51772(12) 0.0269(3) Uani 1 1 d . . . H4 H 1.3497 1.0036 0.5574 0.032 Uiso 1 1 calc R . . C5 C 1.16842(15) 0.93515(11) 0.55459(11) 0.0211(3) Uani 1 1 d . . . H5 H 1.1686 0.9172 0.6198 0.025 Uiso 1 1 calc R . . C6 C 1.05965(13) 0.90875(10) 0.49767(10) 0.0164(3) Uani 1 1 d . . . C7 C 0.98359(16) 0.76204(11) 0.58917(10) 0.0223(3) Uani 1 1 d . . . H7A H 0.9204 0.7106 0.5695 0.033 Uiso 1 1 calc R . . H7B H 0.9754 0.7729 0.6577 0.033 Uiso 1 1 calc R . . H7C H 1.0756 0.7414 0.5742 0.033 Uiso 1 1 calc R . . C8 C 0.81819(14) 0.87768(10) 0.53000(10) 0.0168(3) Uani 1 1 d . . . C9 C 0.64767(15) 1.00010(13) 0.49856(12) 0.0269(3) Uani 1 1 d . . . H9A H 0.5940 0.9976 0.5568 0.040 Uiso 1 1 calc R . . H9B H 0.6123 0.9524 0.4528 0.040 Uiso 1 1 calc R . . H9C H 0.6429 1.0664 0.4714 0.040 Uiso 1 1 calc R . . C10 C 0.86676(14) 1.05146(10) 0.56430(10) 0.0176(3) Uani 1 1 d . . . C11 C 0.91008(15) 1.04247(10) 0.65794(10) 0.0190(3) Uani 1 1 d . . . C12 C 0.99359(15) 1.11470(12) 0.69652(12) 0.0267(3) Uani 1 1 d . . . H12 H 1.0277 1.1070 0.7590 0.032 Uiso 1 1 calc R . . C13 C 1.02699(18) 1.19716(12) 0.64464(13) 0.0336(4) Uani 1 1 d . . . H13 H 1.0828 1.2466 0.6715 0.040 Uiso 1 1 calc R . . C14 C 0.9786(2) 1.20743(12) 0.55326(13) 0.0360(4) Uani 1 1 d . . . H14 H 0.9995 1.2651 0.5180 0.043 Uiso 1 1 calc R . . C15 C 0.90024(17) 1.13470(11) 0.51251(11) 0.0268(3) Uani 1 1 d . . . H15 H 0.8694 1.1418 0.4491 0.032 Uiso 1 1 calc R . . C16 C 0.86819(18) 0.95836(11) 0.71776(10) 0.0233(3) Uani 1 1 d . . . H16 H 0.7903 0.9224 0.6997 0.028 Uiso 1 1 calc R . . C17 C 0.97258(15) 0.78784(11) 0.27107(10) 0.0197(3) Uani 1 1 d . . . C18 C 0.95166(16) 0.71138(10) 0.34817(10) 0.0225(3) Uani 1 1 d . . . H18A H 0.9611 0.6453 0.3210 0.034 Uiso 1 1 calc R . . H18B H 0.8614 0.7188 0.3752 0.034 Uiso 1 1 calc R . . H18C H 1.0190 0.7206 0.3982 0.034 Uiso 1 1 calc R . . C19 C 0.87232(17) 0.77327(12) 0.18978(11) 0.0282(3) Uani 1 1 d . . . H19A H 0.7804 0.7764 0.2147 0.042 Uiso 1 1 calc R . . H19B H 0.8874 0.7089 0.1603 0.042 Uiso 1 1 calc R . . H19C H 0.8850 0.8252 0.1423 0.042 Uiso 1 1 calc R . . C20 C 1.11681(16) 0.78792(12) 0.23466(12) 0.0282(4) Uani 1 1 d . . . H20A H 1.1349 0.7260 0.2014 0.042 Uiso 1 1 calc R . . H20B H 1.1789 0.7947 0.2883 0.042 Uiso 1 1 calc R . . H20C H 1.1294 0.8432 0.1908 0.042 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 0.02159(17) 0.01610(16) 0.01589(16) 0.00027(13) -0.00150(14) 0.00253(14) O1 0.0404(7) 0.0218(5) 0.0230(5) 0.0072(4) -0.0050(5) 0.0023(5) O2 0.0199(5) 0.0232(5) 0.0319(6) -0.0038(5) 0.0034(5) -0.0058(4) O3 0.0716(9) 0.0276(6) 0.0218(6) -0.0008(5) -0.0151(6) 0.0098(6) N1 0.0174(6) 0.0142(5) 0.0176(6) 0.0019(4) 0.0017(5) 0.0019(4) N2 0.0157(6) 0.0196(6) 0.0165(6) -0.0020(5) -0.0016(5) 0.0027(5) C1 0.0171(7) 0.0135(6) 0.0189(7) -0.0026(5) 0.0005(5) 0.0006(5) C2 0.0262(8) 0.0198(7) 0.0247(7) -0.0007(6) 0.0067(6) -0.0002(6) C3 0.0204(8) 0.0209(8) 0.0399(9) -0.0027(7) 0.0097(7) -0.0055(6) C4 0.0176(7) 0.0267(8) 0.0364(9) -0.0093(7) -0.0024(6) 0.0009(6) C5 0.0199(7) 0.0221(7) 0.0214(7) -0.0046(6) -0.0010(6) 0.0043(6) C6 0.0147(6) 0.0136(6) 0.0208(7) -0.0021(5) 0.0013(5) 0.0035(6) C7 0.0302(8) 0.0172(7) 0.0195(7) 0.0029(6) 0.0046(6) 0.0049(6) C8 0.0184(7) 0.0192(7) 0.0128(7) -0.0034(5) 0.0022(5) -0.0013(6) C9 0.0203(8) 0.0318(8) 0.0286(8) -0.0033(7) -0.0051(6) 0.0083(7) C10 0.0172(7) 0.0159(7) 0.0198(7) -0.0030(5) 0.0038(6) 0.0027(5) C11 0.0198(7) 0.0174(7) 0.0198(7) -0.0045(5) 0.0008(6) 0.0047(6) C12 0.0264(8) 0.0261(8) 0.0277(8) -0.0112(6) -0.0024(6) 0.0033(6) C13 0.0342(9) 0.0247(8) 0.0419(10) -0.0159(7) 0.0094(8) -0.0092(7) C14 0.0512(11) 0.0207(8) 0.0361(10) -0.0032(7) 0.0197(8) -0.0094(8) C15 0.0403(10) 0.0206(7) 0.0194(7) -0.0005(6) 0.0070(7) 0.0011(7) C16 0.0358(8) 0.0180(7) 0.0159(7) -0.0058(6) 0.0008(6) 0.0065(6) C17 0.0236(7) 0.0185(7) 0.0171(7) -0.0034(6) -0.0002(6) 0.0044(6) C18 0.0290(8) 0.0159(7) 0.0227(7) -0.0002(6) -0.0034(6) 0.0032(6) C19 0.0364(9) 0.0256(8) 0.0226(8) -0.0057(7) -0.0091(7) 0.0067(7) C20 0.0292(8) 0.0280(8) 0.0275(8) -0.0075(7) 0.0077(7) 0.0022(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 O1 1.5031(11) . ? S1 C1 1.8107(14) . ? S1 C17 1.8581(14) . ? O2 C8 1.2179(17) . ? O3 C16 1.2166(19) . ? N1 C8 1.3817(18) . ? N1 C6 1.4210(17) . ? N1 C7 1.4693(17) . ? N2 C8 1.3756(18) . ? N2 C10 1.4287(18) . ? N2 C9 1.4678(18) . ? C1 C2 1.388(2) . ? C1 C6 1.4032(19) . ? C2 C3 1.389(2) . ? C2 H2 0.9500 . ? C3 C4 1.386(2) . ? C3 H3 0.9500 . ? C4 C5 1.381(2) . ? C4 H4 0.9500 . ? C5 C6 1.394(2) . ? C5 H5 0.9500 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 C15 1.386(2) . ? C10 C11 1.394(2) . ? C11 C12 1.396(2) . ? C11 C16 1.480(2) . ? C12 C13 1.378(2) . ? C12 H12 0.9500 . ? C13 C14 1.382(3) . ? C13 H13 0.9500 . ? C14 C15 1.383(2) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 C18 1.517(2) . ? C17 C20 1.524(2) . ? C17 C19 1.532(2) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? 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 C1 104.78(6) . . ? O1 S1 C17 106.25(6) . . ? C1 S1 C17 102.14(6) . . ? C8 N1 C6 124.52(11) . . ? C8 N1 C7 116.33(12) . . ? C6 N1 C7 119.06(11) . . ? C8 N2 C10 122.39(12) . . ? C8 N2 C9 116.34(12) . . ? C10 N2 C9 116.90(12) . . ? C2 C1 C6 120.03(13) . . ? C2 C1 S1 116.63(11) . . ? C6 C1 S1 123.15(11) . . ? C1 C2 C3 120.53(14) . . ? C1 C2 H2 119.7 . . ? C3 C2 H2 119.7 . . ? C4 C3 C2 119.55(14) . . ? C4 C3 H3 120.2 . . ? C2 C3 H3 120.2 . . ? C5 C4 C3 120.22(15) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.9 . . ? C4 C5 C6 121.01(14) . . ? C4 C5 H5 119.5 . . ? C6 C5 H5 119.5 . . ? C5 C6 C1 118.61(13) . . ? C5 C6 N1 118.90(12) . . ? C1 C6 N1 122.47(12) . . ? N1 C7 H7A 109.5 . . ? N1 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? N1 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? O2 C8 N2 122.35(13) . . ? O2 C8 N1 121.12(13) . . ? N2 C8 N1 116.53(12) . . ? N2 C9 H9A 109.5 . . ? N2 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N2 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C15 C10 C11 119.71(14) . . ? C15 C10 N2 119.29(13) . . ? C11 C10 N2 121.00(13) . . ? C10 C11 C12 119.42(14) . . ? C10 C11 C16 121.33(13) . . ? C12 C11 C16 119.24(13) . . ? C13 C12 C11 120.54(15) . . ? C13 C12 H12 119.7 . . ? C11 C12 H12 119.7 . . ? C12 C13 C14 119.51(15) . . ? C12 C13 H13 120.2 . . ? C14 C13 H13 120.2 . . ? C13 C14 C15 120.72(15) . . ? C13 C14 H14 119.6 . . ? C15 C14 H14 119.6 . . ? C14 C15 C10 119.96(15) . . ? C14 C15 H15 120.0 . . ? C10 C15 H15 120.0 . . ? O3 C16 C11 123.44(16) . . ? O3 C16 H16 118.3 . . ? C11 C16 H16 118.3 . . ? C18 C17 C20 111.76(13) . . ? C18 C17 C19 110.97(13) . . ? C20 C17 C19 111.17(13) . . ? C18 C17 S1 107.74(9) . . ? C20 C17 S1 111.59(11) . . ? C19 C17 S1 103.24(10) . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C17 C20 H20A 109.5 . . ? C17 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C17 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 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 O1 S1 C1 C2 -17.63(12) . . . . ? C17 S1 C1 C2 93.02(11) . . . . ? O1 S1 C1 C6 157.33(11) . . . . ? C17 S1 C1 C6 -92.01(12) . . . . ? C6 C1 C2 C3 2.8(2) . . . . ? S1 C1 C2 C3 177.91(11) . . . . ? C1 C2 C3 C4 -1.1(2) . . . . ? C2 C3 C4 C5 -0.6(2) . . . . ? C3 C4 C5 C6 0.8(2) . . . . ? C4 C5 C6 C1 0.8(2) . . . . ? C4 C5 C6 N1 178.79(13) . . . . ? C2 C1 C6 C5 -2.6(2) . . . . ? S1 C1 C6 C5 -177.38(10) . . . . ? C2 C1 C6 N1 179.51(12) . . . . ? S1 C1 C6 N1 4.71(19) . . . . ? C8 N1 C6 C5 130.37(14) . . . . ? C7 N1 C6 C5 -53.19(17) . . . . ? C8 N1 C6 C1 -51.73(19) . . . . ? C7 N1 C6 C1 124.72(14) . . . . ? C10 N2 C8 O2 147.42(14) . . . . ? C9 N2 C8 O2 -8.4(2) . . . . ? C10 N2 C8 N1 -32.31(19) . . . . ? C9 N2 C8 N1 171.91(12) . . . . ? C6 N1 C8 O2 150.44(13) . . . . ? C7 N1 C8 O2 -26.09(19) . . . . ? C6 N1 C8 N2 -29.83(19) . . . . ? C7 N1 C8 N2 153.64(12) . . . . ? C8 N2 C10 C15 135.89(15) . . . . ? C9 N2 C10 C15 -68.46(17) . . . . ? C8 N2 C10 C11 -44.10(19) . . . . ? C9 N2 C10 C11 111.55(16) . . . . ? C15 C10 C11 C12 -3.9(2) . . . . ? N2 C10 C11 C12 176.09(13) . . . . ? C15 C10 C11 C16 175.46(13) . . . . ? N2 C10 C11 C16 -4.6(2) . . . . ? C10 C11 C12 C13 3.7(2) . . . . ? C16 C11 C12 C13 -175.66(14) . . . . ? C11 C12 C13 C14 -0.9(2) . . . . ? C12 C13 C14 C15 -1.8(3) . . . . ? C13 C14 C15 C10 1.6(3) . . . . ? C11 C10 C15 C14 1.3(2) . . . . ? N2 C10 C15 C14 -178.68(15) . . . . ? C10 C11 C16 O3 159.99(14) . . . . ? C12 C11 C16 O3 -20.7(2) . . . . ? O1 S1 C17 C18 -178.00(10) . . . . ? C1 S1 C17 C18 72.46(11) . . . . ? O1 S1 C17 C20 58.96(12) . . . . ? C1 S1 C17 C20 -50.59(12) . . . . ? O1 S1 C17 C19 -60.53(11) . . . . ? C1 S1 C17 C19 -170.07(10) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.38 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.288 _refine_diff_density_min -0.145 _refine_diff_density_rms 0.040 # Attachment 's2273m1.cif' data_s2273m _database_code_depnum_ccdc_archive 'CCDC 703571' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H30 N2 O3 S' _chemical_formula_weight 450.58 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 Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 8.9041(6) _cell_length_b 10.7195(7) _cell_length_c 24.6200(16) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2349.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5122 _cell_measurement_theta_min 2.52 _cell_measurement_theta_max 26.38 _exptl_crystal_description prismatic _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.274 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 960 _exptl_absorpt_coefficient_mu 0.168 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9359 _exptl_absorpt_correction_T_max 0.9514 _exptl_absorpt_process_details ? _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13333 _diffrn_reflns_av_R_equivalents 0.0410 _diffrn_reflns_av_sigmaI/netI 0.0302 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 1.65 _diffrn_reflns_theta_max 26.39 _reflns_number_total 4799 _reflns_number_gt 4634 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0408P)^2^+0.2839P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.01(5) _chemical_absolute_configuration ad _refine_ls_number_reflns 4799 _refine_ls_number_parameters 295 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0285 _refine_ls_R_factor_gt 0.0276 _refine_ls_wR_factor_ref 0.0724 _refine_ls_wR_factor_gt 0.0720 _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_restrained_S_all 1.072 _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 0.32651(3) 0.92571(3) 0.797269(13) 0.01865(8) Uani 1 1 d . . . O1 O 0.48248(11) 0.91329(11) 0.82023(4) 0.0295(2) Uani 1 1 d . . . O2 O -0.02810(11) 1.10457(9) 0.78513(4) 0.0232(2) Uani 1 1 d . . . O3 O -0.32015(11) 0.85961(9) 0.90062(4) 0.0221(2) Uani 1 1 d . . . H3 H -0.3966 0.8698 0.8811 0.033 Uiso 1 1 calc R . . N1 N -0.02183(12) 0.89880(10) 0.80772(4) 0.0167(2) Uani 1 1 d . . . N2 N 0.06682(12) 1.05242(11) 0.86769(4) 0.0179(2) Uani 1 1 d . . . C1 C 0.22171(15) 0.79798(12) 0.82659(5) 0.0174(3) Uani 1 1 d . . . C2 C 0.06430(15) 0.80031(12) 0.83044(5) 0.0170(3) Uani 1 1 d . . . C3 C -0.00842(16) 0.70118(13) 0.85572(5) 0.0203(3) Uani 1 1 d . . . H3A H -0.1149 0.7005 0.8579 0.024 Uiso 1 1 calc R . . C4 C 0.07340(17) 0.60331(13) 0.87783(6) 0.0240(3) Uani 1 1 d . . . H4 H 0.0226 0.5357 0.8947 0.029 Uiso 1 1 calc R . . C5 C 0.22953(17) 0.60391(14) 0.87541(6) 0.0252(3) Uani 1 1 d . . . H5 H 0.2855 0.5375 0.8910 0.030 Uiso 1 1 calc R . . C6 C 0.30279(16) 0.70176(13) 0.85015(5) 0.0216(3) Uani 1 1 d . . . H6 H 0.4094 0.7030 0.8489 0.026 Uiso 1 1 calc R . . C7 C -0.14191(15) 0.86756(13) 0.76894(5) 0.0214(3) Uani 1 1 d . . . H7A H -0.2395 0.8726 0.7872 0.032 Uiso 1 1 calc R . . H7B H -0.1265 0.7827 0.7552 0.032 Uiso 1 1 calc R . . H7C H -0.1397 0.9266 0.7386 0.032 Uiso 1 1 calc R . . C8 C 0.00367(14) 1.02395(13) 0.81826(5) 0.0172(3) Uani 1 1 d . . . C9 C 0.13012(17) 1.17772(13) 0.87348(6) 0.0243(3) Uani 1 1 d . . . H9A H 0.1878 1.1988 0.8409 0.036 Uiso 1 1 calc R . . H9B H 0.1963 1.1801 0.9053 0.036 Uiso 1 1 calc R . . H9C H 0.0486 1.2382 0.8782 0.036 Uiso 1 1 calc R . . C10 C 0.04554(15) 0.98039(12) 0.91633(5) 0.0169(3) Uani 1 1 d . . . C11 C -0.09622(14) 0.94740(12) 0.93585(5) 0.0172(3) Uani 1 1 d . . . C12 C -0.10476(16) 0.88350(13) 0.98519(6) 0.0209(3) Uani 1 1 d . . . H12 H -0.2005 0.8603 0.9989 0.025 Uiso 1 1 calc R . . C13 C 0.02274(17) 0.85312(13) 1.01462(6) 0.0231(3) Uani 1 1 d . . . H13 H 0.0142 0.8096 1.0481 0.028 Uiso 1 1 calc R . . C14 C 0.16285(17) 0.88676(13) 0.99484(6) 0.0231(3) Uani 1 1 d . . . H14 H 0.2509 0.8665 1.0148 0.028 Uiso 1 1 calc R . . C15 C 0.17401(15) 0.94988(13) 0.94599(5) 0.0202(3) Uani 1 1 d . . . H15 H 0.2701 0.9727 0.9325 0.024 Uiso 1 1 calc R . . C16 C -0.24275(14) 0.97522(13) 0.90612(5) 0.0181(3) Uani 1 1 d . . . H16 H -0.2184 1.0076 0.8691 0.022 Uiso 1 1 calc R . . C17 C -0.33620(14) 1.07211(13) 0.93577(5) 0.0175(2) Uani 1 1 d . . . C18 C -0.44266(15) 1.03990(14) 0.97469(6) 0.0227(3) Uani 1 1 d . . . H18 H -0.4565 0.9549 0.9843 0.027 Uiso 1 1 calc R . . C19 C -0.52871(17) 1.13162(16) 0.99952(6) 0.0282(3) Uani 1 1 d . . . H19 H -0.6010 1.1089 1.0261 0.034 Uiso 1 1 calc R . . C20 C -0.51012(18) 1.25583(16) 0.98581(6) 0.0283(3) Uani 1 1 d . . . H20 H -0.5704 1.3181 1.0025 0.034 Uiso 1 1 calc R . . C21 C -0.40275(17) 1.28895(14) 0.94750(6) 0.0272(3) Uani 1 1 d . . . H21 H -0.3882 1.3741 0.9383 0.033 Uiso 1 1 calc R . . C22 C -0.31686(16) 1.19722(13) 0.92280(6) 0.0224(3) Uani 1 1 d . . . H22 H -0.2436 1.2203 0.8966 0.027 Uiso 1 1 calc R . . C23 C 0.34354(15) 0.87788(13) 0.72499(5) 0.0188(3) Uani 1 1 d . . . C24 C 0.18737(15) 0.88758(13) 0.69988(5) 0.0198(3) Uani 1 1 d . . . H24A H 0.1958 0.8858 0.6602 0.030 Uiso 1 1 calc R . . H24B H 0.1403 0.9660 0.7112 0.030 Uiso 1 1 calc R . . H24C H 0.1258 0.8172 0.7121 0.030 Uiso 1 1 calc R . . C25 C 0.41232(17) 0.74859(14) 0.72050(6) 0.0255(3) Uani 1 1 d . . . H25A H 0.4377 0.7315 0.6825 0.038 Uiso 1 1 calc R . . H25B H 0.3401 0.6863 0.7334 0.038 Uiso 1 1 calc R . . H25C H 0.5035 0.7446 0.7427 0.038 Uiso 1 1 calc R . . C26 C 0.44766(17) 0.97681(15) 0.70096(6) 0.0285(3) Uani 1 1 d . . . H26A H 0.5430 0.9770 0.7209 0.043 Uiso 1 1 calc R . . H26B H 0.4002 1.0590 0.7040 0.043 Uiso 1 1 calc R . . H26C H 0.4666 0.9578 0.6626 0.043 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 0.01602(14) 0.02316(16) 0.01677(15) -0.00217(13) 0.00032(12) -0.00252(13) O1 0.0187(5) 0.0473(7) 0.0224(5) -0.0010(5) -0.0033(4) -0.0067(5) O2 0.0269(5) 0.0214(5) 0.0213(5) 0.0028(4) -0.0019(4) 0.0033(4) O3 0.0207(5) 0.0215(5) 0.0241(5) -0.0040(4) -0.0031(4) -0.0019(4) N1 0.0160(5) 0.0192(6) 0.0151(5) -0.0024(4) -0.0018(4) 0.0013(4) N2 0.0198(5) 0.0180(6) 0.0159(5) -0.0005(4) 0.0010(4) -0.0024(5) C1 0.0190(6) 0.0192(6) 0.0140(6) -0.0016(5) 0.0013(5) -0.0009(5) C2 0.0201(6) 0.0175(6) 0.0133(6) -0.0033(5) 0.0003(5) 0.0018(5) C3 0.0199(6) 0.0218(7) 0.0192(6) -0.0029(5) 0.0009(5) -0.0009(6) C4 0.0331(8) 0.0189(7) 0.0198(7) 0.0002(6) 0.0019(6) -0.0012(6) C5 0.0328(8) 0.0242(7) 0.0185(7) 0.0012(6) -0.0022(6) 0.0092(6) C6 0.0218(7) 0.0260(7) 0.0169(6) -0.0026(6) -0.0008(5) 0.0056(6) C7 0.0184(6) 0.0256(7) 0.0202(6) -0.0045(5) -0.0027(5) 0.0004(6) C8 0.0150(6) 0.0193(6) 0.0173(6) -0.0004(5) 0.0028(5) 0.0020(5) C9 0.0297(8) 0.0197(7) 0.0235(7) -0.0014(6) -0.0003(6) -0.0051(6) C10 0.0210(6) 0.0153(6) 0.0143(6) -0.0029(5) 0.0002(5) 0.0003(5) C11 0.0184(6) 0.0164(6) 0.0167(6) -0.0028(5) -0.0006(5) 0.0017(5) C12 0.0229(7) 0.0213(6) 0.0186(6) -0.0015(5) 0.0017(5) -0.0009(6) C13 0.0304(8) 0.0209(7) 0.0178(6) 0.0024(5) -0.0022(6) 0.0037(6) C14 0.0256(7) 0.0233(7) 0.0203(6) -0.0028(5) -0.0062(6) 0.0062(6) C15 0.0175(6) 0.0228(6) 0.0202(6) -0.0054(5) 0.0003(5) 0.0024(6) C16 0.0173(6) 0.0216(7) 0.0153(6) -0.0015(5) -0.0003(5) -0.0007(5) C17 0.0151(5) 0.0224(6) 0.0150(5) -0.0020(5) -0.0029(5) 0.0011(6) C18 0.0219(6) 0.0241(7) 0.0222(7) -0.0002(6) 0.0023(5) 0.0000(6) C19 0.0236(7) 0.0368(9) 0.0242(7) -0.0046(7) 0.0051(6) 0.0026(7) C20 0.0276(8) 0.0319(8) 0.0255(8) -0.0113(6) -0.0043(6) 0.0079(7) C21 0.0288(7) 0.0226(7) 0.0302(8) -0.0031(6) -0.0056(6) 0.0004(6) C22 0.0217(7) 0.0241(7) 0.0214(7) 0.0019(5) -0.0025(6) -0.0022(6) C23 0.0189(6) 0.0238(6) 0.0137(6) -0.0012(5) 0.0010(5) -0.0005(6) C24 0.0213(6) 0.0224(6) 0.0159(6) -0.0014(5) -0.0008(5) 0.0001(5) C25 0.0273(7) 0.0298(7) 0.0193(7) -0.0022(6) 0.0013(6) 0.0087(6) C26 0.0268(7) 0.0362(8) 0.0225(7) -0.0003(7) 0.0037(6) -0.0098(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 S1 O1 1.5053(10) . ? S1 C1 1.8074(14) . ? S1 C23 1.8580(13) . ? O2 C8 1.2215(16) . ? O3 C16 1.4246(17) . ? O3 H3 0.8400 . ? N1 C8 1.3851(17) . ? N1 C2 1.4198(17) . ? N1 C7 1.4720(16) . ? N2 C8 1.3751(17) . ? N2 C10 1.4374(17) . ? N2 C9 1.4636(17) . ? C1 C6 1.3861(19) . ? C1 C2 1.4050(19) . ? C2 C3 1.391(2) . ? C3 C4 1.388(2) . ? C3 H3A 0.9500 . ? C4 C5 1.391(2) . ? C4 H4 0.9500 . ? C5 C6 1.383(2) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 C11 1.3961(18) . ? C10 C15 1.3960(18) . ? C11 C12 1.3965(19) . ? C11 C16 1.5255(17) . ? C12 C13 1.386(2) . ? C12 H12 0.9500 . ? C13 C14 1.387(2) . ? C13 H13 0.9500 . ? C14 C15 1.384(2) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? C16 C17 1.5178(18) . ? C16 H16 1.0000 . ? C17 C22 1.389(2) . ? C17 C18 1.3915(19) . ? C18 C19 1.388(2) . ? C18 H18 0.9500 . ? C19 C20 1.383(2) . ? C19 H19 0.9500 . ? C20 C21 1.389(2) . ? C20 H20 0.9500 . ? C21 C22 1.386(2) . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? C23 C25 1.519(2) . ? C23 C24 1.5254(18) . ? C23 C26 1.528(2) . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? 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 C1 105.03(6) . . ? O1 S1 C23 105.07(6) . . ? C1 S1 C23 102.45(6) . . ? C16 O3 H3 109.5 . . ? C8 N1 C2 123.91(11) . . ? C8 N1 C7 117.45(11) . . ? C2 N1 C7 118.60(11) . . ? C8 N2 C10 124.35(11) . . ? C8 N2 C9 116.57(11) . . ? C10 N2 C9 117.56(11) . . ? C6 C1 C2 120.31(13) . . ? C6 C1 S1 117.51(10) . . ? C2 C1 S1 121.90(11) . . ? C3 C2 C1 118.74(13) . . ? C3 C2 N1 119.53(12) . . ? C1 C2 N1 121.71(12) . . ? C4 C3 C2 120.55(13) . . ? C4 C3 H3A 119.7 . . ? C2 C3 H3A 119.7 . . ? C3 C4 C5 120.26(14) . . ? C3 C4 H4 119.9 . . ? C5 C4 H4 119.9 . . ? C6 C5 C4 119.61(13) . . ? C6 C5 H5 120.2 . . ? C4 C5 H5 120.2 . . ? C5 C6 C1 120.45(13) . . ? C5 C6 H6 119.8 . . ? C1 C6 H6 119.8 . . ? N1 C7 H7A 109.5 . . ? N1 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? N1 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? O2 C8 N2 121.91(12) . . ? O2 C8 N1 121.48(12) . . ? N2 C8 N1 116.60(11) . . ? N2 C9 H9A 109.5 . . ? N2 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N2 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C11 C10 C15 120.10(12) . . ? C11 C10 N2 122.82(11) . . ? C15 C10 N2 116.97(12) . . ? C10 C11 C12 118.22(12) . . ? C10 C11 C16 123.95(11) . . ? C12 C11 C16 117.82(12) . . ? C13 C12 C11 121.70(13) . . ? C13 C12 H12 119.2 . . ? C11 C12 H12 119.1 . . ? C12 C13 C14 119.50(13) . . ? C12 C13 H13 120.3 . . ? C14 C13 H13 120.3 . . ? C15 C14 C13 119.79(13) . . ? C15 C14 H14 120.1 . . ? C13 C14 H14 120.1 . . ? C14 C15 C10 120.69(13) . . ? C14 C15 H15 119.7 . . ? C10 C15 H15 119.7 . . ? O3 C16 C17 112.07(11) . . ? O3 C16 C11 106.82(11) . . ? C17 C16 C11 111.83(10) . . ? O3 C16 H16 108.7 . . ? C17 C16 H16 108.7 . . ? C11 C16 H16 108.7 . . ? C22 C17 C18 118.83(13) . . ? C22 C17 C16 118.82(12) . . ? C18 C17 C16 122.34(13) . . ? C19 C18 C17 120.23(14) . . ? C19 C18 H18 119.9 . . ? C17 C18 H18 119.9 . . ? C20 C19 C18 120.54(14) . . ? C20 C19 H19 119.7 . . ? C18 C19 H19 119.7 . . ? C19 C20 C21 119.60(14) . . ? C19 C20 H20 120.2 . . ? C21 C20 H20 120.2 . . ? C22 C21 C20 119.75(15) . . ? C22 C21 H21 120.1 . . ? C20 C21 H21 120.1 . . ? C21 C22 C17 121.04(13) . . ? C21 C22 H22 119.5 . . ? C17 C22 H22 119.5 . . ? C25 C23 C24 113.59(11) . . ? C25 C23 C26 111.13(12) . . ? C24 C23 C26 110.41(11) . . ? C25 C23 S1 110.75(9) . . ? C24 C23 S1 107.16(9) . . ? C26 C23 S1 103.24(9) . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C23 C25 H25A 109.5 . . ? C23 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C23 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C23 C26 H26A 109.5 . . ? C23 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C23 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 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 O1 S1 C1 C6 -16.05(12) . . . . ? C23 S1 C1 C6 93.52(11) . . . . ? O1 S1 C1 C2 157.88(11) . . . . ? C23 S1 C1 C2 -92.55(12) . . . . ? C6 C1 C2 C3 -3.4(2) . . . . ? S1 C1 C2 C3 -177.12(10) . . . . ? C6 C1 C2 N1 178.71(12) . . . . ? S1 C1 C2 N1 4.94(19) . . . . ? C8 N1 C2 C3 129.28(14) . . . . ? C7 N1 C2 C3 -53.21(17) . . . . ? C8 N1 C2 C1 -52.80(18) . . . . ? C7 N1 C2 C1 124.71(14) . . . . ? C1 C2 C3 C4 1.5(2) . . . . ? N1 C2 C3 C4 179.46(12) . . . . ? C2 C3 C4 C5 0.6(2) . . . . ? C3 C4 C5 C6 -0.9(2) . . . . ? C4 C5 C6 C1 -1.0(2) . . . . ? C2 C1 C6 C5 3.1(2) . . . . ? S1 C1 C6 C5 177.16(11) . . . . ? C10 N2 C8 O2 150.09(13) . . . . ? C9 N2 C8 O2 -15.48(19) . . . . ? C10 N2 C8 N1 -30.12(18) . . . . ? C9 N2 C8 N1 164.31(11) . . . . ? C2 N1 C8 O2 151.66(12) . . . . ? C7 N1 C8 O2 -25.87(19) . . . . ? C2 N1 C8 N2 -28.13(18) . . . . ? C7 N1 C8 N2 154.33(11) . . . . ? C8 N2 C10 C11 -52.01(19) . . . . ? C9 N2 C10 C11 113.43(14) . . . . ? C8 N2 C10 C15 131.77(13) . . . . ? C9 N2 C10 C15 -62.78(16) . . . . ? C15 C10 C11 C12 -0.21(19) . . . . ? N2 C10 C11 C12 -176.31(12) . . . . ? C15 C10 C11 C16 -179.26(12) . . . . ? N2 C10 C11 C16 4.6(2) . . . . ? C10 C11 C12 C13 0.2(2) . . . . ? C16 C11 C12 C13 179.27(13) . . . . ? C11 C12 C13 C14 0.0(2) . . . . ? C12 C13 C14 C15 -0.2(2) . . . . ? C13 C14 C15 C10 0.1(2) . . . . ? C11 C10 C15 C14 0.1(2) . . . . ? N2 C10 C15 C14 176.40(12) . . . . ? C10 C11 C16 O3 125.70(13) . . . . ? C12 C11 C16 O3 -53.35(15) . . . . ? C10 C11 C16 C17 -111.34(14) . . . . ? C12 C11 C16 C17 69.61(16) . . . . ? O3 C16 C17 C22 -149.11(12) . . . . ? C11 C16 C17 C22 90.96(15) . . . . ? O3 C16 C17 C18 29.58(17) . . . . ? C11 C16 C17 C18 -90.34(15) . . . . ? C22 C17 C18 C19 0.7(2) . . . . ? C16 C17 C18 C19 -178.00(13) . . . . ? C17 C18 C19 C20 0.2(2) . . . . ? C18 C19 C20 C21 -1.0(2) . . . . ? C19 C20 C21 C22 0.9(2) . . . . ? C20 C21 C22 C17 -0.1(2) . . . . ? C18 C17 C22 C21 -0.8(2) . . . . ? C16 C17 C22 C21 177.98(12) . . . . ? O1 S1 C23 C25 55.05(11) . . . . ? C1 S1 C23 C25 -54.50(11) . . . . ? O1 S1 C23 C24 179.44(9) . . . . ? C1 S1 C23 C24 69.90(10) . . . . ? O1 S1 C23 C26 -63.97(10) . . . . ? C1 S1 C23 C26 -173.51(9) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O3 H3 O1 0.84 1.90 2.7086(14) 160.1 1_455 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.39 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.316 _refine_diff_density_min -0.162 _refine_diff_density_rms 0.040