# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2009 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Adrian Dobbs' _publ_contact_author_email A.DOBBS@QMUL.AC.UK _publ_section_title ; The Aza-Prins reaction ; loop_ _publ_author_name 'Adrian Dobbs' 'Sebastien J.J. Guesne' 'Michael B Hursthouse' 'Robert J Parker' 'John Skidmore' ; R.A.Stephenson ; # Attachment '2006src1366.cif' data_2006src1366 _database_code_depnum_ccdc_archive 'CCDC 748949' # Dr Adrian Dobbs _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H28 Cl N O2 S' _chemical_formula_weight 369.93 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21 ' 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 9.5924(3) _cell_length_b 12.9905(3) _cell_length_c 15.0218(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1871.87(9) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 2442 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description slab _exptl_crystal_colour colourless _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.42 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.313 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 792 _exptl_absorpt_coefficient_mu 0.327 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8483 _exptl_absorpt_correction_T_max 0.9743 _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, G.M., 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius 95mm CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16779 _diffrn_reflns_av_R_equivalents 0.0484 _diffrn_reflns_av_sigmaI/netI 0.0514 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.97 _diffrn_reflns_theta_max 27.50 _reflns_number_total 4283 _reflns_number_gt 3656 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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. Refined as inversion twin of 23.887% using Twin instruction in ShelX ; _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^)+(0.0424P)^2^+0.3456P] 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 0.24(6) _refine_ls_number_reflns 4283 _refine_ls_number_parameters 220 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0516 _refine_ls_R_factor_gt 0.0376 _refine_ls_wR_factor_ref 0.0886 _refine_ls_wR_factor_gt 0.0826 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.24973(6) 0.50840(3) 0.31560(3) 0.01630(11) Uani 1 1 d . . . Cl1 Cl 0.42172(6) 0.23950(4) 0.50857(4) 0.02927(15) Uani 1 1 d . . . O1 O 0.12095(16) 0.55137(11) 0.28549(10) 0.0230(4) Uani 1 1 d . . . O2 O 0.37945(16) 0.55032(11) 0.28526(10) 0.0211(3) Uani 1 1 d . . . N1 N 0.2483(2) 0.51776(11) 0.42324(10) 0.0165(3) Uani 1 1 d . . . C1 C 0.3683(2) 0.47301(15) 0.47363(14) 0.0165(4) Uani 1 1 d . . . H1 H 0.4111 0.4173 0.4367 0.020 Uiso 1 1 calc R . . C2 C 0.2994(2) 0.42342(15) 0.55544(14) 0.0171(4) Uani 1 1 d . . . H2 H 0.3588 0.4352 0.6092 0.021 Uiso 1 1 calc R . . C3 C 0.1617(2) 0.48249(16) 0.56540(15) 0.0210(5) Uani 1 1 d . . . H3A H 0.0922 0.4414 0.5987 0.025 Uiso 1 1 calc R . . H3B H 0.1763 0.5488 0.5965 0.025 Uiso 1 1 calc R . . C4 C 0.1154(2) 0.49958(16) 0.46973(14) 0.0182(4) Uani 1 1 d . . . H4A H 0.0671 0.4382 0.4458 0.022 Uiso 1 1 calc R . . H4B H 0.0529 0.5600 0.4649 0.022 Uiso 1 1 calc R . . C5 C 0.2685(2) 0.30806(14) 0.54574(13) 0.0172(4) Uani 1 1 d . . . H5 H 0.1934 0.2991 0.5002 0.021 Uiso 1 1 calc R . . C6 C 0.2208(2) 0.25874(16) 0.63168(14) 0.0243(5) Uani 1 1 d . . . H6A H 0.2936 0.2666 0.6770 0.036 Uiso 1 1 calc R . . H6B H 0.2030 0.1854 0.6216 0.036 Uiso 1 1 calc R . . H6C H 0.1351 0.2923 0.6521 0.036 Uiso 1 1 calc R . . C7 C 0.4798(2) 0.55424(14) 0.49281(15) 0.0190(4) Uani 1 1 d . . . H7 H 0.5058 0.5853 0.4342 0.023 Uiso 1 1 calc R . . C8 C 0.4311(2) 0.64272(15) 0.55228(15) 0.0244(5) Uani 1 1 d . . . H8A H 0.3482 0.6758 0.5254 0.029 Uiso 1 1 calc R . . H8B H 0.4040 0.6153 0.6113 0.029 Uiso 1 1 calc R . . C9 C 0.5463(2) 0.72243(17) 0.56372(16) 0.0307(5) Uani 1 1 d . . . H9A H 0.5678 0.7539 0.5053 0.037 Uiso 1 1 calc R . . H9B H 0.5135 0.7777 0.6040 0.037 Uiso 1 1 calc R . . C10 C 0.6774(3) 0.67436(19) 0.60180(17) 0.0331(6) Uani 1 1 d . . . H10A H 0.6583 0.6491 0.6628 0.040 Uiso 1 1 calc R . . H10B H 0.7515 0.7272 0.6056 0.040 Uiso 1 1 calc R . . C11 C 0.7278(3) 0.58512(18) 0.54415(17) 0.0329(6) Uani 1 1 d . . . H11A H 0.8087 0.5517 0.5731 0.039 Uiso 1 1 calc R . . H11B H 0.7586 0.6118 0.4856 0.039 Uiso 1 1 calc R . . C12 C 0.6118(2) 0.50569(17) 0.53046(16) 0.0253(5) Uani 1 1 d . . . H12A H 0.6450 0.4516 0.4892 0.030 Uiso 1 1 calc R . . H12B H 0.5899 0.4726 0.5881 0.030 Uiso 1 1 calc R . . C13 C 0.2508(2) 0.37675(13) 0.28725(12) 0.0156(4) Uani 1 1 d . . . C14 C 0.3733(2) 0.32984(16) 0.26119(14) 0.0193(5) Uani 1 1 d . . . H14 H 0.4571 0.3685 0.2579 0.023 Uiso 1 1 calc R . . C15 C 0.3734(2) 0.22669(17) 0.23996(14) 0.0223(5) Uani 1 1 d . . . H15 H 0.4577 0.1948 0.2215 0.027 Uiso 1 1 calc R . . C16 C 0.2518(3) 0.16858(14) 0.24519(13) 0.0208(4) Uani 1 1 d . . . C17 C 0.1299(2) 0.21695(16) 0.27172(14) 0.0211(5) Uani 1 1 d . . . H17 H 0.0463 0.1781 0.2759 0.025 Uiso 1 1 calc R . . C18 C 0.1278(2) 0.32094(16) 0.29227(13) 0.0186(4) Uani 1 1 d . . . H18 H 0.0433 0.3535 0.3095 0.022 Uiso 1 1 calc R . . C19 C 0.2524(3) 0.05544(14) 0.22221(16) 0.0280(5) Uani 1 1 d . . . H19A H 0.2937 0.0164 0.2714 0.042 Uiso 1 1 calc R . . H19B H 0.3072 0.0445 0.1680 0.042 Uiso 1 1 calc R . . H19C H 0.1565 0.0320 0.2124 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 0.0216(2) 0.0151(2) 0.0122(2) 0.00195(18) 0.0000(2) -0.0003(2) Cl1 0.0276(3) 0.0232(3) 0.0370(3) 0.0062(2) 0.0070(3) 0.0097(2) O1 0.0275(8) 0.0217(7) 0.0196(8) 0.0035(7) -0.0031(7) 0.0049(7) O2 0.0255(8) 0.0213(7) 0.0165(8) 0.0033(6) 0.0027(7) -0.0066(7) N1 0.0206(8) 0.0178(7) 0.0110(8) -0.0001(6) -0.0004(8) 0.0014(8) C1 0.0203(10) 0.0167(9) 0.0124(10) 0.0000(8) -0.0001(8) 0.0016(8) C2 0.0201(10) 0.0188(10) 0.0125(10) -0.0011(9) -0.0002(8) -0.0023(8) C3 0.0260(11) 0.0212(10) 0.0156(10) -0.0012(9) 0.0048(9) 0.0005(9) C4 0.0201(10) 0.0187(10) 0.0158(10) 0.0029(8) 0.0030(8) 0.0022(9) C5 0.0151(10) 0.0185(9) 0.0181(10) 0.0004(8) -0.0002(9) 0.0019(8) C6 0.0310(12) 0.0192(9) 0.0226(11) 0.0033(9) 0.0024(10) -0.0041(9) C7 0.0241(10) 0.0191(9) 0.0139(10) -0.0007(8) 0.0028(9) -0.0051(8) C8 0.0367(13) 0.0183(10) 0.0181(11) -0.0024(9) 0.0002(11) -0.0040(10) C9 0.0475(14) 0.0230(11) 0.0217(11) -0.0006(10) 0.0029(11) -0.0150(11) C10 0.0402(14) 0.0345(12) 0.0245(13) -0.0028(11) -0.0008(11) -0.0201(12) C11 0.0297(14) 0.0407(12) 0.0284(13) -0.0009(10) -0.0009(11) -0.0108(11) C12 0.0247(12) 0.0275(11) 0.0237(12) -0.0024(10) -0.0016(9) -0.0049(10) C13 0.0198(9) 0.0167(8) 0.0103(9) 0.0010(7) -0.0004(10) -0.0009(10) C14 0.0194(11) 0.0233(10) 0.0153(11) -0.0006(9) -0.0022(9) -0.0010(9) C15 0.0218(10) 0.0236(11) 0.0214(11) -0.0025(9) 0.0008(9) 0.0034(9) C16 0.0281(11) 0.0191(9) 0.0151(10) -0.0006(8) 0.0017(11) 0.0016(11) C17 0.0218(11) 0.0222(10) 0.0194(11) -0.0006(9) 0.0015(9) -0.0059(9) C18 0.0198(10) 0.0214(10) 0.0147(11) -0.0036(9) 0.0027(9) -0.0011(9) C19 0.0353(12) 0.0190(9) 0.0298(12) -0.0032(9) 0.0066(13) 0.0010(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O1 1.4292(16) . ? S1 O2 1.4327(16) . ? S1 N1 1.6215(16) . ? S1 C13 1.7625(17) . ? Cl1 C5 1.807(2) . ? N1 C4 1.472(3) . ? N1 C1 1.495(3) . ? C1 C7 1.530(3) . ? C1 C2 1.537(3) . ? C1 H1 1.0000 . ? C2 C3 1.534(3) . ? C2 C5 1.534(3) . ? C2 H2 1.0000 . ? C3 C4 1.521(3) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.512(3) . ? C5 H5 1.0000 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 C12 1.523(3) . ? C7 C8 1.529(3) . ? C7 H7 1.0000 . ? C8 C9 1.523(3) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.517(3) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.526(3) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.532(3) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.380(3) . ? C13 C18 1.387(3) . ? C14 C15 1.377(3) . ? C14 H14 0.9500 . ? C15 C16 1.391(3) . ? C15 H15 0.9500 . ? C16 C17 1.386(3) . ? C16 C19 1.510(3) . ? C17 C18 1.386(3) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 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 O2 120.10(8) . . ? O1 S1 N1 106.21(10) . . ? O2 S1 N1 107.22(10) . . ? O1 S1 C13 107.90(10) . . ? O2 S1 C13 106.68(10) . . ? N1 S1 C13 108.29(8) . . ? C4 N1 C1 111.35(14) . . ? C4 N1 S1 117.91(14) . . ? C1 N1 S1 117.98(14) . . ? N1 C1 C7 111.43(16) . . ? N1 C1 C2 103.67(16) . . ? C7 C1 C2 116.06(17) . . ? N1 C1 H1 108.5 . . ? C7 C1 H1 108.5 . . ? C2 C1 H1 108.5 . . ? C3 C2 C5 109.37(16) . . ? C3 C2 C1 103.81(16) . . ? C5 C2 C1 114.60(17) . . ? C3 C2 H2 109.6 . . ? C5 C2 H2 109.6 . . ? C1 C2 H2 109.6 . . ? C4 C3 C2 103.42(17) . . ? C4 C3 H3A 111.1 . . ? C2 C3 H3A 111.1 . . ? C4 C3 H3B 111.1 . . ? C2 C3 H3B 111.1 . . ? H3A C3 H3B 109.0 . . ? N1 C4 C3 102.64(16) . . ? N1 C4 H4A 111.2 . . ? C3 C4 H4A 111.2 . . ? N1 C4 H4B 111.2 . . ? C3 C4 H4B 111.2 . . ? H4A C4 H4B 109.2 . . ? C6 C5 C2 113.02(17) . . ? C6 C5 Cl1 107.52(13) . . ? C2 C5 Cl1 110.73(14) . . ? C6 C5 H5 108.5 . . ? C2 C5 H5 108.5 . . ? Cl1 C5 H5 108.5 . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C12 C7 C8 110.37(18) . . ? C12 C7 C1 111.43(16) . . ? C8 C7 C1 114.54(18) . . ? C12 C7 H7 106.7 . . ? C8 C7 H7 106.7 . . ? C1 C7 H7 106.7 . . ? C9 C8 C7 110.83(18) . . ? C9 C8 H8A 109.5 . . ? C7 C8 H8A 109.5 . . ? C9 C8 H8B 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 108.1 . . ? C10 C9 C8 111.34(18) . . ? C10 C9 H9A 109.4 . . ? C8 C9 H9A 109.4 . . ? C10 C9 H9B 109.4 . . ? C8 C9 H9B 109.4 . . ? H9A C9 H9B 108.0 . . ? C9 C10 C11 111.2(2) . . ? C9 C10 H10A 109.4 . . ? C11 C10 H10A 109.4 . . ? C9 C10 H10B 109.4 . . ? C11 C10 H10B 109.4 . . ? H10A C10 H10B 108.0 . . ? C10 C11 C12 111.0(2) . . ? C10 C11 H11A 109.4 . . ? C12 C11 H11A 109.4 . . ? C10 C11 H11B 109.4 . . ? C12 C11 H11B 109.4 . . ? H11A C11 H11B 108.0 . . ? C7 C12 C11 112.02(18) . . ? C7 C12 H12A 109.2 . . ? C11 C12 H12A 109.2 . . ? C7 C12 H12B 109.2 . . ? C11 C12 H12B 109.2 . . ? H12A C12 H12B 107.9 . . ? C14 C13 C18 120.57(16) . . ? C14 C13 S1 120.12(17) . . ? C18 C13 S1 119.30(16) . . ? C15 C14 C13 119.7(2) . . ? C15 C14 H14 120.1 . . ? C13 C14 H14 120.1 . . ? C14 C15 C16 120.9(2) . . ? C14 C15 H15 119.5 . . ? C16 C15 H15 119.5 . . ? C17 C16 C15 118.51(17) . . ? C17 C16 C19 120.7(2) . . ? C15 C16 C19 120.8(2) . . ? C16 C17 C18 121.2(2) . . ? C16 C17 H17 119.4 . . ? C18 C17 H17 119.4 . . ? C17 C18 C13 119.0(2) . . ? C17 C18 H18 120.5 . . ? C13 C18 H18 120.5 . . ? C16 C19 H19A 109.5 . . ? C16 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C16 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.247 _refine_diff_density_min -0.372 _refine_diff_density_rms 0.056 # Attachment '2006src1365.cif' data_b _database_code_depnum_ccdc_archive 'CCDC 748950' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H26 Cl N O2 S' _chemical_formula_weight 391.94 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C 1 2/c 1 ' 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 24.2931(8) _cell_length_b 11.7455(3) _cell_length_c 14.3281(4) _cell_angle_alpha 90.00 _cell_angle_beta 105.602(2) _cell_angle_gamma 90.00 _cell_volume 3937.7(2) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 4653 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.322 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1664 _exptl_absorpt_coefficient_mu 0.315 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8842 _exptl_absorpt_correction_T_max 0.9454 _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, G.M., 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius 95mm CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22425 _diffrn_reflns_av_R_equivalents 0.0566 _diffrn_reflns_av_sigmaI/netI 0.0504 _diffrn_reflns_limit_h_min -31 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.14 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4514 _reflns_number_gt 3063 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0621P)^2^+1.8311P] 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 4514 _refine_ls_number_parameters 305 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0830 _refine_ls_R_factor_gt 0.0494 _refine_ls_wR_factor_ref 0.1356 _refine_ls_wR_factor_gt 0.1195 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.065 _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 N1 N 0.34442(8) 0.91016(14) -0.02966(12) 0.0357(4) Uani 1 1 d D . . Cl1 Cl 0.38250(4) 0.72336(5) -0.28242(4) 0.0697(3) Uani 1 1 d . . . C1 C 0.29570(10) 0.86798(18) -0.10582(18) 0.0452(6) Uani 1 1 d . A . H1A H 0.2759 0.9332 -0.1444 0.054 Uiso 1 1 calc R . . H1B H 0.2683 0.8304 -0.0756 0.054 Uiso 1 1 calc R . . C2 C 0.31350(10) 0.78452(17) -0.17249(17) 0.0431(5) Uani 1 1 d . . . H2A H 0.3259 0.7125 -0.1372 0.052 Uiso 1 1 calc R A . H2B H 0.2803 0.7676 -0.2282 0.052 Uiso 1 1 calc R . . C3 C 0.36148(10) 0.83100(16) -0.20904(14) 0.0361(5) Uani 1 1 d . A . H3 H 0.3476 0.8996 -0.2499 0.043 Uiso 1 1 calc R . . C4 C 0.41173(8) 0.86414(16) -0.12640(14) 0.0313(4) Uani 1 1 d . . . H4 H 0.4234 0.7948 -0.0853 0.038 Uiso 1 1 calc R A . C5 C 0.39246(9) 0.95381(16) -0.06343(14) 0.0317(4) Uani 1 1 d . A . H5 H 0.4251 0.9664 -0.0048 0.038 Uiso 1 1 calc R . . C6 C 0.46401(10) 0.9045(2) -0.1560(2) 0.0546(7) Uani 1 1 d . A . H6A H 0.4824 0.8393 -0.1779 0.082 Uiso 1 1 calc R . . H6B H 0.4910 0.9403 -0.1004 0.082 Uiso 1 1 calc R . . H6C H 0.4524 0.9599 -0.2088 0.082 Uiso 1 1 calc R . . C7 C 0.37666(10) 1.06985(16) -0.11207(15) 0.0357(5) Uani 1 1 d . . . H7A H 0.4057 1.0919 -0.1456 0.043 Uiso 1 1 calc R A . H7B H 0.3394 1.0638 -0.1613 0.043 Uiso 1 1 calc R . . C8 C 0.37304(13) 1.16081(19) -0.03960(18) 0.0575(7) Uani 1 1 d . A . H8A H 0.4123 1.1803 -0.0014 0.069 Uiso 1 1 calc R . . H8B H 0.3526 1.1292 0.0057 0.069 Uiso 1 1 calc R . . C9 C 0.34321(10) 1.26876(16) -0.08361(16) 0.0408(5) Uani 1 1 d . . . C10 C 0.30323(11) 1.31753(19) -0.04389(18) 0.0511(6) Uani 1 1 d . A . H10 H 0.2949 1.2822 0.0104 0.061 Uiso 1 1 calc R . . C11 C 0.27502(11) 1.4160(2) -0.08060(19) 0.0531(6) Uani 1 1 d . . . H11 H 0.2469 1.4468 -0.0527 0.064 Uiso 1 1 calc R A . C12 C 0.28735(10) 1.46963(18) -0.15692(18) 0.0489(6) Uani 1 1 d . A . H12 H 0.2681 1.5379 -0.1821 0.059 Uiso 1 1 calc R . . C13 C 0.32797(11) 1.42411(19) -0.19733(18) 0.0499(6) Uani 1 1 d . . . H13 H 0.3374 1.4622 -0.2494 0.060 Uiso 1 1 calc R A . C14 C 0.35527(10) 1.32226(19) -0.16191(17) 0.0442(5) Uani 1 1 d . A . H14 H 0.3821 1.2896 -0.1916 0.053 Uiso 1 1 calc R . . S1A S 0.36559(16) 0.8662(5) 0.0868(4) 0.0434(10) Uani 0.50 1 d PD A 1 O2A O 0.3134(3) 0.8453(6) 0.1098(5) 0.0522(17) Uani 0.50 1 d P A 1 O1A O 0.4070(2) 0.9432(5) 0.1437(4) 0.0577(14) Uani 0.50 1 d P A 1 C15A C 0.39061(16) 0.7408(5) 0.0919(4) 0.0341(19) Uani 0.50 1 d PG A 1 C16A C 0.36973(14) 0.6337(5) 0.0589(5) 0.0250(17) Uani 0.50 1 d PG A 1 H16A H 0.3305 0.6244 0.0255 0.030 Uiso 0.50 1 calc PR A 1 C17A C 0.4062(2) 0.5403(4) 0.0746(4) 0.0280(14) Uani 0.50 1 d PG A 1 H17A H 0.3919 0.4672 0.0521 0.034 Uiso 0.50 1 calc PR A 1 C18A C 0.46357(19) 0.5540(3) 0.1235(3) 0.0341(13) Uani 0.50 1 d PG A 1 C19A C 0.48445(13) 0.6610(3) 0.1565(2) 0.0373(10) Uani 0.50 1 d PG A 1 H19A H 0.5236 0.6703 0.1899 0.045 Uiso 0.50 1 calc PR A 1 C20A C 0.44797(18) 0.7544(3) 0.1407(3) 0.0365(12) Uani 0.50 1 d PG A 1 H20A H 0.4622 0.8275 0.1633 0.044 Uiso 0.50 1 calc PR A 1 C21A C 0.5009(3) 0.4514(5) 0.1411(4) 0.0507(13) Uani 0.50 1 d P A 1 H21A H 0.4809 0.3879 0.1018 0.076 Uiso 0.50 1 calc PR A 1 H21B H 0.5100 0.4307 0.2099 0.076 Uiso 0.50 1 calc PR A 1 H21C H 0.5363 0.4678 0.1234 0.076 Uiso 0.50 1 calc PR A 1 S1B S 0.34702(15) 0.8635(5) 0.0745(4) 0.0315(7) Uani 0.50 1 d PD A 2 O2B O 0.2909(2) 0.8287(6) 0.0803(5) 0.0392(14) Uani 0.50 1 d P A 2 O1B O 0.37646(18) 0.9511(4) 0.1371(4) 0.0379(11) Uani 0.50 1 d P A 2 C15B C 0.40139(18) 0.7375(4) 0.0924(4) 0.0282(16) Uani 0.50 1 d PG A 2 C16B C 0.36850(14) 0.6390(6) 0.0758(6) 0.036(2) Uani 0.50 1 d PG A 2 H16B H 0.3283 0.6434 0.0664 0.043 Uiso 0.50 1 calc PR A 2 C17B C 0.3944(2) 0.5340(4) 0.0730(5) 0.045(2) Uani 0.50 1 d PG A 2 H17B H 0.3719 0.4666 0.0616 0.053 Uiso 0.50 1 calc PR A 2 C18B C 0.4532(2) 0.5275(3) 0.0868(3) 0.0371(14) Uani 0.50 1 d PG A 2 C19B C 0.48606(14) 0.6260(3) 0.1034(3) 0.0443(11) Uani 0.50 1 d PG A 2 H19B H 0.5262 0.6216 0.1128 0.053 Uiso 0.50 1 calc PR A 2 C20B C 0.46017(17) 0.7311(3) 0.1062(3) 0.0397(12) Uani 0.50 1 d PG A 2 H20B H 0.4826 0.7984 0.1175 0.048 Uiso 0.50 1 calc PR A 2 C21B C 0.4847(3) 0.4138(5) 0.0855(4) 0.0567(16) Uani 0.50 1 d P A 2 H21D H 0.5258 0.4280 0.0990 0.085 Uiso 0.50 1 calc PR A 2 H21E H 0.4708 0.3782 0.0216 0.085 Uiso 0.50 1 calc PR A 2 H21F H 0.4774 0.3629 0.1351 0.085 Uiso 0.50 1 calc PR A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0468(11) 0.0288(8) 0.0374(9) 0.0088(7) 0.0215(9) 0.0085(8) Cl1 0.1373(7) 0.0384(3) 0.0361(3) -0.0004(2) 0.0280(4) 0.0279(4) C1 0.0337(13) 0.0396(12) 0.0660(15) 0.0151(11) 0.0197(12) 0.0027(9) C2 0.0434(13) 0.0298(10) 0.0469(12) 0.0047(9) -0.0036(10) -0.0055(9) C3 0.0537(14) 0.0238(9) 0.0295(10) 0.0019(8) 0.0091(10) 0.0091(9) C4 0.0333(11) 0.0281(9) 0.0351(10) 0.0081(8) 0.0140(9) 0.0062(8) C5 0.0352(11) 0.0267(9) 0.0314(10) 0.0020(8) 0.0062(9) -0.0005(8) C6 0.0422(14) 0.0537(14) 0.0771(17) 0.0204(13) 0.0321(13) 0.0124(11) C7 0.0437(13) 0.0250(9) 0.0403(11) 0.0044(8) 0.0143(10) -0.0002(9) C8 0.086(2) 0.0289(11) 0.0489(13) -0.0005(10) 0.0027(14) 0.0134(12) C9 0.0496(14) 0.0241(10) 0.0434(12) -0.0020(9) 0.0033(11) 0.0009(9) C10 0.0689(18) 0.0326(11) 0.0508(14) -0.0033(10) 0.0144(13) -0.0012(11) C11 0.0553(16) 0.0397(12) 0.0601(15) -0.0072(12) 0.0082(13) 0.0060(11) C12 0.0480(15) 0.0267(10) 0.0570(14) -0.0060(10) -0.0117(12) 0.0032(10) C13 0.0515(15) 0.0387(12) 0.0517(13) 0.0110(11) 0.0006(12) -0.0130(11) C14 0.0375(13) 0.0407(12) 0.0505(13) 0.0037(11) 0.0051(11) 0.0017(10) S1A 0.075(3) 0.0319(10) 0.0289(13) 0.0055(9) 0.0241(18) 0.009(2) O2A 0.071(5) 0.048(3) 0.058(4) 0.020(3) 0.052(4) 0.022(3) O1A 0.102(4) 0.035(2) 0.0309(19) -0.0071(15) 0.008(3) -0.002(3) C15A 0.023(3) 0.053(5) 0.026(4) 0.006(3) 0.007(3) -0.006(3) C16A 0.029(4) 0.026(3) 0.022(3) -0.005(2) 0.012(2) -0.006(3) C17A 0.024(3) 0.026(3) 0.037(4) 0.010(3) 0.012(2) 0.004(2) C18A 0.029(3) 0.046(3) 0.025(3) 0.016(2) 0.003(2) 0.006(2) C19A 0.029(2) 0.049(3) 0.032(2) 0.003(2) 0.004(2) 0.004(2) C20A 0.039(3) 0.044(3) 0.032(3) 0.006(2) 0.017(2) 0.004(2) C21A 0.057(4) 0.054(3) 0.048(3) 0.016(3) 0.027(3) 0.023(3) S1B 0.0424(16) 0.0244(7) 0.0315(13) 0.0002(7) 0.0165(13) 0.0007(12) O2B 0.030(3) 0.039(2) 0.055(4) 0.010(2) 0.024(2) 0.005(2) O1B 0.054(3) 0.0324(19) 0.0302(19) -0.0064(14) 0.016(2) -0.005(2) C15B 0.042(3) 0.019(3) 0.022(4) 0.006(3) 0.004(3) -0.001(2) C16B 0.038(4) 0.038(4) 0.035(3) 0.008(3) 0.017(3) 0.010(3) C17B 0.040(4) 0.048(4) 0.053(5) 0.007(4) 0.025(3) 0.008(3) C18B 0.040(4) 0.043(3) 0.024(3) 0.010(2) 0.000(2) 0.004(2) C19B 0.032(3) 0.056(3) 0.039(3) 0.010(2) 0.000(2) 0.008(2) C20B 0.031(3) 0.049(3) 0.036(3) 0.006(2) 0.003(2) -0.007(2) C21B 0.080(4) 0.051(3) 0.048(3) 0.017(3) 0.032(3) 0.033(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.464(3) . ? N1 C5 1.470(3) . ? N1 S1B 1.574(6) . ? N1 S1A 1.689(5) . ? Cl1 C3 1.8037(19) . ? C1 C2 1.511(3) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C3 1.503(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.505(3) . ? C3 H3 1.0000 . ? C4 C6 1.519(3) . ? C4 C5 1.539(3) . ? C4 H4 1.0000 . ? C5 C7 1.532(3) . ? C5 H5 1.0000 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 C8 1.509(3) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.512(3) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.376(3) . ? C9 C14 1.384(3) . ? C10 C11 1.375(3) . ? C10 H10 0.9500 . ? C11 C12 1.363(4) . ? C11 H11 0.9500 . ? C12 C13 1.379(3) . ? C12 H12 0.9500 . ? C13 C14 1.396(3) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? S1A O2A 1.414(7) . ? S1A O1A 1.433(8) . ? S1A C15A 1.588(7) . ? C15A C16A 1.3900 . ? C15A C20A 1.3900 . ? C16A C17A 1.3900 . ? C16A H16A 0.9500 . ? C17A C18A 1.3900 . ? C17A H17A 0.9500 . ? C18A C19A 1.3900 . ? C18A C21A 1.488(6) . ? C19A C20A 1.3900 . ? C19A H19A 0.9500 . ? C20A H20A 0.9500 . ? C21A H21A 0.9800 . ? C21A H21B 0.9800 . ? C21A H21C 0.9800 . ? S1B O1B 1.425(8) . ? S1B O2B 1.447(6) . ? S1B C15B 1.954(6) . ? C15B C16B 1.3900 . ? C15B C20B 1.3900 . ? C16B C17B 1.3900 . ? C16B H16B 0.9500 . ? C17B C18B 1.3900 . ? C17B H17B 0.9500 . ? C18B C19B 1.3900 . ? C18B C21B 1.542(6) . ? C19B C20B 1.3900 . ? C19B H19B 0.9500 . ? C20B H20B 0.9500 . ? C21B H21D 0.9800 . ? C21B H21E 0.9800 . ? C21B H21F 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 C1 N1 C5 115.26(16) . . ? C1 N1 S1B 114.0(2) . . ? C5 N1 S1B 126.87(19) . . ? C1 N1 S1A 127.1(2) . . ? C5 N1 S1A 111.96(19) . . ? S1B N1 S1A 14.9(2) . . ? N1 C1 C2 112.30(17) . . ? N1 C1 H1A 109.1 . . ? C2 C1 H1A 109.1 . . ? N1 C1 H1B 109.1 . . ? C2 C1 H1B 109.1 . . ? H1A C1 H1B 107.9 . . ? C3 C2 C1 111.43(17) . . ? C3 C2 H2A 109.3 . . ? C1 C2 H2A 109.3 . . ? C3 C2 H2B 109.3 . . ? C1 C2 H2B 109.3 . . ? H2A C2 H2B 108.0 . . ? C2 C3 C4 111.14(16) . . ? C2 C3 Cl1 108.43(14) . . ? C4 C3 Cl1 110.05(14) . . ? C2 C3 H3 109.1 . . ? C4 C3 H3 109.1 . . ? Cl1 C3 H3 109.1 . . ? C3 C4 C6 115.04(18) . . ? C3 C4 C5 109.13(16) . . ? C6 C4 C5 111.05(17) . . ? C3 C4 H4 107.1 . . ? C6 C4 H4 107.1 . . ? C5 C4 H4 107.1 . . ? N1 C5 C7 109.64(16) . . ? N1 C5 C4 110.35(15) . . ? C7 C5 C4 114.87(16) . . ? N1 C5 H5 107.2 . . ? C7 C5 H5 107.2 . . ? C4 C5 H5 107.2 . . ? C4 C6 H6A 109.5 . . ? C4 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C4 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C8 C7 C5 111.76(17) . . ? C8 C7 H7A 109.3 . . ? C5 C7 H7A 109.3 . . ? C8 C7 H7B 109.3 . . ? C5 C7 H7B 109.3 . . ? H7A C7 H7B 107.9 . . ? C7 C8 C9 114.65(19) . . ? C7 C8 H8A 108.6 . . ? C9 C8 H8A 108.6 . . ? C7 C8 H8B 108.6 . . ? C9 C8 H8B 108.6 . . ? H8A C8 H8B 107.6 . . ? C10 C9 C14 118.2(2) . . ? C10 C9 C8 119.3(2) . . ? C14 C9 C8 122.5(2) . . ? C11 C10 C9 121.8(2) . . ? C11 C10 H10 119.1 . . ? C9 C10 H10 119.1 . . ? C12 C11 C10 120.1(2) . . ? C12 C11 H11 120.0 . . ? C10 C11 H11 120.0 . . ? C11 C12 C13 119.6(2) . . ? C11 C12 H12 120.2 . . ? C13 C12 H12 120.2 . . ? C12 C13 C14 120.2(2) . . ? C12 C13 H13 119.9 . . ? C14 C13 H13 119.9 . . ? C9 C14 C13 120.0(2) . . ? C9 C14 H14 120.0 . . ? C13 C14 H14 120.0 . . ? O2A S1A O1A 120.8(5) . . ? O2A S1A C15A 100.6(5) . . ? O1A S1A C15A 111.0(4) . . ? O2A S1A N1 103.3(3) . . ? O1A S1A N1 110.5(4) . . ? C15A S1A N1 109.9(4) . . ? C16A C15A C20A 120.0 . . ? C16A C15A S1A 136.3(3) . . ? C20A C15A S1A 103.7(3) . . ? C15A C16A C17A 120.0 . . ? C15A C16A H16A 120.0 . . ? C17A C16A H16A 120.0 . . ? C16A C17A C18A 120.0 . . ? C16A C17A H17A 120.0 . . ? C18A C17A H17A 120.0 . . ? C19A C18A C17A 120.0 . . ? C19A C18A C21A 121.6(4) . . ? C17A C18A C21A 118.3(4) . . ? C18A C19A C20A 120.0 . . ? C18A C19A H19A 120.0 . . ? C20A C19A H19A 120.0 . . ? C19A C20A C15A 120.0 . . ? C19A C20A H20A 120.0 . . ? C15A C20A H20A 120.0 . . ? O1B S1B O2B 119.2(5) . . ? O1B S1B N1 103.4(4) . . ? O2B S1B N1 110.8(4) . . ? O1B S1B C15B 104.9(3) . . ? O2B S1B C15B 113.1(5) . . ? N1 S1B C15B 104.0(3) . . ? C16B C15B C20B 120.0 . . ? C16B C15B S1B 105.7(3) . . ? C20B C15B S1B 133.8(3) . . ? C15B C16B C17B 120.0 . . ? C15B C16B H16B 120.0 . . ? C17B C16B H16B 120.0 . . ? C18B C17B C16B 120.0 . . ? C18B C17B H17B 120.0 . . ? C16B C17B H17B 120.0 . . ? C17B C18B C19B 120.0 . . ? C17B C18B C21B 122.7(4) . . ? C19B C18B C21B 117.3(4) . . ? C20B C19B C18B 120.0 . . ? C20B C19B H19B 120.0 . . ? C18B C19B H19B 120.0 . . ? C19B C20B C15B 120.0 . . ? C19B C20B H20B 120.0 . . ? C15B C20B H20B 120.0 . . ? C18B C21B H21D 109.5 . . ? C18B C21B H21E 109.5 . . ? H21D C21B H21E 109.5 . . ? C18B C21B H21F 109.5 . . ? H21D C21B H21F 109.5 . . ? H21E C21B H21F 109.5 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.325 _refine_diff_density_min -0.444 _refine_diff_density_rms 0.051 # Attachment '2007src0763.cif' data_2007src0763 _database_code_depnum_ccdc_archive 'CCDC 748951' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Dr F. H. Fry ; _chemical_name_common 'Dr F. H. Fry' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H28 Cl N O2 S' _chemical_formula_weight 369.93 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P na2(1)' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, z' _cell_length_a 15.4076(3) _cell_length_b 12.9924(4) _cell_length_c 9.3800(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1877.70(9) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 12291 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Rod _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.309 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 792 _exptl_absorpt_coefficient_mu 0.326 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6519 _exptl_absorpt_correction_T_max 0.7458 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _exptl_special_details ; SADABS was used to perform the Absorption correction and gives the estimated minimum and maximum transmission values as 0.6519 and 0.7458. ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius APEX II CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean '4096x4096pixels / 62x62mm' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10624 _diffrn_reflns_av_R_equivalents 0.0506 _diffrn_reflns_av_sigmaI/netI 0.0598 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.99 _diffrn_reflns_theta_max 28.50 _reflns_number_total 4506 _reflns_number_gt 4215 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution ; Sir2004 (Burla, M.C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R., 2004) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON/PLUTON (Spek, A. L., 1998)' _computing_publication_material 'WinGX (Farrugia, 1999)' _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. The refined Flack parameter for this structure is 0.40 (12) using 1994, 79 % Friedel pairs. The inverted structure gives a Flack parameter of 0.59 (12). For this reason the structure has been refined as an inversion twin with the ratio of enantiomers being 0.40 (12). ; _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^)+(0.0627P)^2^+4.7927P] 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, 1994 Friedel pairs' _refine_ls_abs_structure_Flack 0.40(12) _chemical_absolute_configuration ad _refine_ls_number_reflns 4506 _refine_ls_number_parameters 220 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0743 _refine_ls_R_factor_gt 0.0699 _refine_ls_wR_factor_ref 0.1761 _refine_ls_wR_factor_gt 0.1726 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.074 _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 0.6588(3) 0.0084(3) 0.4155(7) 0.0303(9) Uani 1 1 d . . . H1A H 0.6527 0.0078 0.3115 0.046 Uiso 1 1 calc R . . H1B H 0.6657 -0.0623 0.4503 0.046 Uiso 1 1 calc R . . H1C H 0.7099 0.0490 0.4420 0.046 Uiso 1 1 calc R . . C2 C 0.5781(3) 0.0562(3) 0.4821(5) 0.0235(8) Uani 1 1 d . . . H2 H 0.5813 0.0473 0.5878 0.028 Uiso 1 1 calc R . . C3 C 0.5669(3) 0.1715(3) 0.4487(5) 0.0236(8) Uani 1 1 d . . . H3 H 0.6174 0.2081 0.4925 0.028 Uiso 1 1 calc R . . C4 C 0.4831(3) 0.2177(3) 0.5167(4) 0.0198(8) Uani 1 1 d . . . H4 H 0.4516 0.1618 0.5683 0.024 Uiso 1 1 calc R . . C5 C 0.4717(3) 0.2159(4) 0.2553(4) 0.0231(9) Uani 1 1 d . . . H5A H 0.4457 0.1506 0.2216 0.028 Uiso 1 1 calc R . . H5B H 0.4645 0.2689 0.1804 0.028 Uiso 1 1 calc R . . C6 C 0.5647(3) 0.2017(4) 0.2915(5) 0.0317(10) Uani 1 1 d . . . H6A H 0.5973 0.2664 0.2758 0.038 Uiso 1 1 calc R . . H6B H 0.5907 0.1469 0.2320 0.038 Uiso 1 1 calc R . . C7 C 0.4989(3) 0.3070(3) 0.6201(4) 0.0198(7) Uani 1 1 d . . . H7 H 0.4406 0.3343 0.6476 0.024 Uiso 1 1 calc R . . C8 C 0.5506(3) 0.3982(3) 0.5568(5) 0.0236(8) Uani 1 1 d . . . H8A H 0.6093 0.3746 0.5289 0.028 Uiso 1 1 calc R . . H8B H 0.5208 0.4238 0.4702 0.028 Uiso 1 1 calc R . . C9 C 0.5584(3) 0.4854(3) 0.6652(5) 0.0277(9) Uani 1 1 d . . . H9A H 0.5000 0.5125 0.6878 0.033 Uiso 1 1 calc R . . H9B H 0.5932 0.5421 0.6239 0.033 Uiso 1 1 calc R . . C10 C 0.6019(3) 0.4469(4) 0.8020(5) 0.0298(9) Uani 1 1 d . . . H10A H 0.6623 0.4258 0.7804 0.036 Uiso 1 1 calc R . . H10B H 0.6043 0.5037 0.8722 0.036 Uiso 1 1 calc R . . C11 C 0.5533(3) 0.3563(4) 0.8666(5) 0.0328(10) Uani 1 1 d . . . H11A H 0.4954 0.3793 0.8993 0.039 Uiso 1 1 calc R . . H11B H 0.5856 0.3302 0.9505 0.039 Uiso 1 1 calc R . . C12 C 0.5428(3) 0.2699(3) 0.7578(5) 0.0266(9) Uani 1 1 d . . . H12A H 0.5076 0.2140 0.8004 0.032 Uiso 1 1 calc R . . H12B H 0.6006 0.2413 0.7345 0.032 Uiso 1 1 calc R . . C13 C 0.2898(2) 0.1193(2) 0.4013(5) 0.0174(6) Uani 1 1 d . . . C14 C 0.2667(3) 0.0712(3) 0.2746(4) 0.0247(9) Uani 1 1 d . . . H14 H 0.2678 0.1085 0.1875 0.030 Uiso 1 1 calc R . . C15 C 0.2420(3) -0.0320(4) 0.2756(5) 0.0294(10) Uani 1 1 d . . . H15 H 0.2265 -0.0649 0.1888 0.035 Uiso 1 1 calc R . . C16 C 0.2397(2) -0.0866(2) 0.4018(5) 0.0209(7) Uani 1 1 d . . . C17 C 0.2623(3) -0.0378(3) 0.5287(5) 0.0255(9) Uani 1 1 d . . . H17 H 0.2607 -0.0749 0.6160 0.031 Uiso 1 1 calc R . . C18 C 0.2872(3) 0.0648(3) 0.5280(5) 0.0228(9) Uani 1 1 d . . . H18 H 0.3025 0.0979 0.6148 0.027 Uiso 1 1 calc R . . C19 C 0.2134(3) -0.1985(3) 0.4030(6) 0.0285(8) Uani 1 1 d . . . H19A H 0.1576 -0.2064 0.3539 0.043 Uiso 1 1 calc R . . H19B H 0.2077 -0.2222 0.5017 0.043 Uiso 1 1 calc R . . H19C H 0.2576 -0.2395 0.3540 0.043 Uiso 1 1 calc R . . N1 N 0.43052(16) 0.2502(2) 0.3934(5) 0.0167(5) Uani 1 1 d . . . O1 O 0.3012(2) 0.2914(2) 0.5357(3) 0.0232(6) Uani 1 1 d . . . O2 O 0.2936(2) 0.2943(2) 0.2706(3) 0.0231(7) Uani 1 1 d . . . S1 S 0.32487(5) 0.24788(6) 0.40037(14) 0.01646(18) Uani 1 1 d . . . Cl1 Cl 0.48551(7) -0.01701(7) 0.41558(19) 0.0411(3) 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 0.0269(18) 0.0181(15) 0.046(3) 0.000(2) 0.006(2) 0.0049(14) C2 0.0212(19) 0.0159(17) 0.033(2) -0.0007(15) -0.0015(16) 0.0008(14) C3 0.0236(19) 0.0178(18) 0.029(2) 0.0005(15) -0.0001(16) -0.0001(14) C4 0.025(2) 0.0166(17) 0.0181(19) -0.0007(14) 0.0011(16) -0.0013(15) C5 0.022(2) 0.031(2) 0.0164(19) 0.0009(16) 0.0048(15) 0.0051(16) C6 0.029(2) 0.031(2) 0.036(3) -0.0028(19) 0.007(2) 0.0046(18) C7 0.0225(18) 0.0159(16) 0.0211(19) -0.0041(14) 0.0032(15) -0.0027(13) C8 0.027(2) 0.0126(16) 0.031(2) -0.0020(15) -0.0014(17) -0.0001(14) C9 0.021(2) 0.0190(19) 0.043(3) -0.0097(17) 0.0017(18) -0.0053(15) C10 0.028(2) 0.031(2) 0.030(2) -0.0098(18) -0.0027(18) -0.0016(17) C11 0.034(2) 0.033(2) 0.031(3) -0.0056(17) -0.0026(18) -0.0061(18) C12 0.030(2) 0.0222(19) 0.027(2) 0.0012(16) -0.0035(18) -0.0015(16) C13 0.0151(14) 0.0146(13) 0.0224(16) 0.0018(18) 0.0017(17) -0.0002(11) C14 0.038(3) 0.021(2) 0.015(2) 0.0006(15) -0.0020(18) -0.0061(17) C15 0.049(3) 0.020(2) 0.019(2) -0.0059(16) -0.004(2) -0.0130(18) C16 0.0187(16) 0.0171(14) 0.0268(18) -0.0040(19) -0.004(2) -0.0020(11) C17 0.033(2) 0.0204(19) 0.023(2) 0.0010(16) 0.0014(17) -0.0092(17) C18 0.027(2) 0.023(2) 0.018(2) -0.0016(16) 0.0000(16) -0.0071(16) C19 0.034(2) 0.0198(16) 0.032(2) 0.004(2) 0.004(2) -0.0046(14) N1 0.0103(11) 0.0180(11) 0.0218(14) -0.0015(13) -0.0056(15) 0.0001(10) O1 0.0252(15) 0.0207(15) 0.0236(16) -0.0074(12) 0.0042(12) -0.0001(12) O2 0.0188(14) 0.0187(15) 0.0318(18) 0.0059(13) -0.0039(12) 0.0043(11) S1 0.0156(3) 0.0134(3) 0.0204(4) -0.0025(4) -0.0002(4) 0.0008(3) Cl1 0.0303(5) 0.0187(4) 0.0743(9) -0.0119(6) 0.0020(7) -0.0035(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.524(6) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C3 1.540(5) . ? C2 Cl1 1.824(4) . ? C2 H2 1.0000 . ? C3 C6 1.526(7) . ? C3 C4 1.560(6) . ? C3 H3 1.0000 . ? C4 N1 1.474(6) . ? C4 C7 1.532(5) . ? C4 H4 1.0000 . ? C5 C6 1.484(6) . ? C5 N1 1.509(6) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C12 1.536(6) . ? C7 C8 1.546(5) . ? C7 H7 1.0000 . ? C8 C9 1.527(5) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.532(7) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.521(7) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.526(6) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C18 1.384(6) . ? C13 C14 1.389(6) . ? C13 S1 1.756(3) . ? C14 C15 1.393(6) . ? C14 H14 0.9500 . ? C15 C16 1.382(7) . ? C15 H15 0.9500 . ? C16 C17 1.393(6) . ? C16 C19 1.509(5) . ? C17 C18 1.388(6) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? N1 S1 1.629(3) . ? O1 S1 1.436(3) . ? O2 S1 1.442(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag 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 . . ? C1 C2 C3 113.8(3) . . ? C1 C2 Cl1 106.6(3) . . ? C3 C2 Cl1 110.5(3) . . ? C1 C2 H2 108.6 . . ? C3 C2 H2 108.6 . . ? Cl1 C2 H2 108.6 . . ? C6 C3 C2 116.7(4) . . ? C6 C3 C4 106.1(3) . . ? C2 C3 C4 112.6(3) . . ? C6 C3 H3 107.0 . . ? C2 C3 H3 107.0 . . ? C4 C3 H3 107.0 . . ? N1 C4 C7 111.6(3) . . ? N1 C4 C3 104.2(3) . . ? C7 C4 C3 114.8(3) . . ? N1 C4 H4 108.7 . . ? C7 C4 H4 108.7 . . ? C3 C4 H4 108.7 . . ? C6 C5 N1 104.2(3) . . ? C6 C5 H5A 110.9 . . ? N1 C5 H5A 110.9 . . ? C6 C5 H5B 110.9 . . ? N1 C5 H5B 110.9 . . ? H5A C5 H5B 108.9 . . ? C5 C6 C3 106.0(4) . . ? C5 C6 H6A 110.5 . . ? C3 C6 H6A 110.5 . . ? C5 C6 H6B 110.5 . . ? C3 C6 H6B 110.5 . . ? H6A C6 H6B 108.7 . . ? C4 C7 C12 111.4(3) . . ? C4 C7 C8 114.8(3) . . ? C12 C7 C8 109.7(3) . . ? C4 C7 H7 106.8 . . ? C12 C7 H7 106.8 . . ? C8 C7 H7 106.8 . . ? C9 C8 C7 110.7(4) . . ? C9 C8 H8A 109.5 . . ? C7 C8 H8A 109.5 . . ? C9 C8 H8B 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 108.1 . . ? C8 C9 C10 110.5(4) . . ? C8 C9 H9A 109.5 . . ? C10 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? C10 C9 H9B 109.5 . . ? H9A C9 H9B 108.1 . . ? C11 C10 C9 111.8(4) . . ? C11 C10 H10A 109.3 . . ? C9 C10 H10A 109.3 . . ? C11 C10 H10B 109.3 . . ? C9 C10 H10B 109.3 . . ? H10A C10 H10B 107.9 . . ? C10 C11 C12 110.8(4) . . ? C10 C11 H11A 109.5 . . ? C12 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? C12 C11 H11B 109.5 . . ? H11A C11 H11B 108.1 . . ? C11 C12 C7 112.2(3) . . ? C11 C12 H12A 109.2 . . ? C7 C12 H12A 109.2 . . ? C11 C12 H12B 109.2 . . ? C7 C12 H12B 109.2 . . ? H12A C12 H12B 107.9 . . ? C18 C13 C14 119.9(3) . . ? C18 C13 S1 119.9(3) . . ? C14 C13 S1 120.2(3) . . ? C13 C14 C15 119.8(4) . . ? C13 C14 H14 120.1 . . ? C15 C14 H14 120.1 . . ? C16 C15 C14 120.5(4) . . ? C16 C15 H15 119.8 . . ? C14 C15 H15 119.8 . . ? C15 C16 C17 119.5(3) . . ? C15 C16 C19 120.5(4) . . ? C17 C16 C19 120.0(4) . . ? C18 C17 C16 120.2(4) . . ? C18 C17 H17 119.9 . . ? C16 C17 H17 119.9 . . ? C13 C18 C17 120.2(4) . . ? C13 C18 H18 119.9 . . ? C17 C18 H18 119.9 . . ? C16 C19 H19A 109.5 . . ? C16 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C16 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C4 N1 C5 110.9(3) . . ? C4 N1 S1 120.9(3) . . ? C5 N1 S1 116.7(3) . . ? O1 S1 O2 119.83(15) . . ? O1 S1 N1 106.3(2) . . ? O2 S1 N1 107.0(2) . . ? O1 S1 C13 107.0(2) . . ? O2 S1 C13 107.4(2) . . ? N1 S1 C13 108.96(15) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 28.50 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 1.193 _refine_diff_density_min -0.769 _refine_diff_density_rms 0.096