Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name M.Moloney _publ_contact_author_address ; Chemistry University of Oxford Chemistry Research Laboratory Mansfield Rd Oxford OX1 3TA UNITED KINGDOM ; _publ_contact_author_email MARK.MOLONEY@CHEMISTRY.OXFORD.AC.UK _publ_section_title ; Trans-2,5-Disubstituted Pyrrolidines: Rapid Stereocontrolled Access from Sulfones ; loop_ _publ_author_name M.Moloney 'Terry Panchal' 'Richard Pike' data_arc1288 _database_code_depnum_ccdc_archive 'CCDC 615009' #============================================================= # Diffractometer details #============================================================= _diffrn_measurement_device_type ; Nonius KappaCCD ; _diffrn_radiation_monochromator graphite _computing_data_collection ; KappaCCD software 'Collect' (Nonius, 2000) ; _computing_data_reduction ; KappaCCD software 'DENZO' (Otwinowski & Minor, 1996) ; _computing_cell_refinement ; KappaCCD software 'DENZO' (Otwinowski & Minor, 1996) ; #============================================================= # General computing #============================================================= _computing_structure_refinement ; CRYSTALS (Watkin et al, 2001) ; _computing_publication_material ; CRYSTALS (Watkin et al, 2001) ; _computing_structure_solution 'SIR92 (Giacovazzo et al, 1992)' _chemical_name_systematic # IUPAC name, in full ; ? ; _chemical_melting_point ? _chemical_absolute_configuration ad _exptl_crystal_thermal_history ; The material was crystallised at ambient temperature. A suitable crystal was cooled rapidly to 150K for single-crystal X-ray diffraction analysis. ; _refine_ls_matrix_type full _atom_sites_solution_primary direct _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment noref #============================================================= _cell_length_a 10.6783(3) _cell_angle_alpha 90 _cell_length_b 8.1891(2) _cell_angle_beta 98.9319(17) _cell_length_c 11.1365(3) _cell_angle_gamma 90 _cell_volume 962.03(4) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21 1 ' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,y+1/2,-z loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source 'C ' 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 International_Tables_Vol_IV_Table_2.2B 'H ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 International_Tables_Vol_IV_Table_2.2B 'N ' 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 International_Tables_Vol_IV_Table_2.2B 'O ' 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 International_Tables_Vol_IV_Table_2.2B 'S ' 0.1246 0.1234 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720 0.8669 International_Tables_Vol_IV_Table_2.2B _cell_formula_units_Z 2 _chemical_formula_sum ' C18 H25 N O6 S ' _chemical_formula_moiety ' C18 H25 N O6 S ' _chemical_compound_source ; synthesis as described ; _chemical_formula_weight 383.47 _cell_measurement_reflns_used 9083 _cell_measurement_theta_min 5 _cell_measurement_theta_max 28 _cell_measurement_temperature 150 _exptl_crystal_description ' fragment ' _exptl_crystal_colour ' colourless ' _exptl_crystal_size_min 0.18 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_max 0.32 _exptl_crystal_density_diffrn 1.324 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 408 _exptl_absorpt_coefficient_mu 0.201 _diffrn_measurement_method \w _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Denzo/Scalepack (Otwinowski & Minor, 1996) ; _exptl_absorpt_correction_T_min 0.94 _exptl_absorpt_correction_T_max 0.96 _diffrn_standards_interval_time 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0.00 _diffrn_ambient_temperature 150 _diffrn_reflns_number 9083 _reflns_number_total 4175 #4183 unqiue reflections including absences _diffrn_reflns_av_R_equivalents 0.039 _diffrn_reflns_theta_min 5.177 _diffrn_reflns_theta_max 27.476 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.476 _diffrn_measured_fraction_theta_full 0.995 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _reflns_limit_h_min -13 _reflns_limit_h_max 13 _reflns_limit_k_min -10 _reflns_limit_k_max 10 _reflns_limit_l_min 0 _reflns_limit_l_max 14 _refine_diff_density_min -0.42 _refine_diff_density_max 0.34 _refine_ls_number_reflns 3226 _refine_ls_number_restraints 1 _refine_ls_number_parameters 236 #_refine_ls_R_factor_ref 0.0334 _refine_ls_wR_factor_ref 0.0340 _refine_ls_goodness_of_fit_ref 1.1154 #_reflns_number_all 4175 _refine_ls_R_factor_all 0.0522 _refine_ls_wR_factor_all 0.0553 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>3.00u(I) _reflns_number_gt 3226 _refine_ls_R_factor_gt 0.0334 _refine_ls_wR_factor_gt 0.0340 _refine_ls_shift/su_max 0.002349 _refine_ls_abs_structure_Flack 0.04(7) _refine_ls_abs_structure_details 'Flack, 1848 Friedel-pairs' _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 0.310 0.0240 0.0616 ; _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 # Uequiv = arithmetic mean of Ui # i.e. Ueqiv = (U1+U2+U3)/3 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_occupancy _atom_site_adp_type N1 N 0.39679(14) 0.3820(2) 0.26585(14) 0.0161 1.0000 Uani C1 C 0.50485(18) 0.3652(3) 0.36097(17) 0.0179 1.0000 Uani C2 C 0.4913(2) 0.1948(3) 0.4158(2) 0.0231 1.0000 Uani C3 C 0.4053(2) 0.1023(3) 0.3153(2) 0.0230 1.0000 Uani C4 C 0.3161(2) 0.2362(3) 0.2541(2) 0.0192 1.0000 Uani C5 C 0.2046(2) 0.2617(3) 0.3225(2) 0.0203 1.0000 Uani O1 O 0.20913(15) 0.3446(2) 0.41247(14) 0.0285 1.0000 Uani O2 O 0.10289(14) 0.1778(2) 0.27051(14) 0.0252 1.0000 Uani C6 C -0.0123(2) 0.1965(3) 0.3264(2) 0.0297 1.0000 Uani C7 C -0.0139(2) 0.0828(3) 0.4314(2) 0.0337 1.0000 Uani C8 C 0.3439(2) 0.5373(3) 0.24604(19) 0.0176 1.0000 Uani O3 O 0.39237(16) 0.65974(18) 0.29006(15) 0.0226 1.0000 Uani O4 O 0.23534(14) 0.52368(18) 0.16735(13) 0.0207 1.0000 Uani C9 C 0.1545(2) 0.6701(3) 0.1353(2) 0.0245 1.0000 Uani C10 C 0.0448(3) 0.5982(3) 0.0480(3) 0.0406 1.0000 Uani C11 C 0.1101(2) 0.7354(3) 0.2484(2) 0.0346 1.0000 Uani C12 C 0.2270(2) 0.7943(3) 0.0722(2) 0.0329 1.0000 Uani S1 S 0.65473(5) 0.37412(8) 0.30277(5) 0.0193 1.0000 Uani O5 O 0.65482(16) 0.24686(19) 0.21271(16) 0.0268 1.0000 Uani O6 O 0.75137(13) 0.3740(3) 0.40889(14) 0.0301 1.0000 Uani C13 C 0.6573(2) 0.5645(3) 0.2299(2) 0.0188 1.0000 Uani C14 C 0.6065(2) 0.5768(3) 0.1069(2) 0.0218 1.0000 Uani C15 C 0.6026(2) 0.7287(3) 0.0514(2) 0.0287 1.0000 Uani C16 C 0.6501(2) 0.8651(3) 0.1180(2) 0.0306 1.0000 Uani C17 C 0.7007(2) 0.8514(3) 0.2396(2) 0.0293 1.0000 Uani C18 C 0.7050(2) 0.6993(3) 0.2965(2) 0.0235 1.0000 Uani H11 H 0.5059 0.4563 0.4210 0.0214 1.0000 Uiso H21 H 0.5757 0.1401 0.4353 0.0280 1.0000 Uiso H22 H 0.4512 0.2022 0.4910 0.0280 1.0000 Uiso H31 H 0.4558 0.0526 0.2562 0.0279 1.0000 Uiso H32 H 0.3564 0.0149 0.3504 0.0279 1.0000 Uiso H41 H 0.2793 0.2091 0.1683 0.0231 1.0000 Uiso H61 H -0.0168 0.3114 0.3558 0.0362 1.0000 Uiso H62 H -0.0879 0.1733 0.2636 0.0362 1.0000 Uiso H71 H -0.0936 0.0997 0.4665 0.0413 1.0000 Uiso H72 H 0.0610 0.1055 0.4950 0.0413 1.0000 Uiso H73 H -0.0101 -0.0326 0.4029 0.0413 1.0000 Uiso H101 H -0.0175 0.6864 0.0193 0.0461 1.0000 Uiso H102 H 0.0775 0.5492 -0.0233 0.0461 1.0000 Uiso H103 H 0.0021 0.5118 0.0906 0.0461 1.0000 Uiso H111 H 0.0557 0.8339 0.2271 0.0421 1.0000 Uiso H112 H 0.1853 0.7662 0.3095 0.0421 1.0000 Uiso H113 H 0.0599 0.6495 0.2835 0.0421 1.0000 Uiso H121 H 0.1727 0.8927 0.0506 0.0390 1.0000 Uiso H122 H 0.3057 0.8270 0.1278 0.0390 1.0000 Uiso H123 H 0.2504 0.7452 -0.0035 0.0390 1.0000 Uiso H141 H 0.5735 0.4778 0.0597 0.0266 1.0000 Uiso H151 H 0.5657 0.7402 -0.0363 0.0351 1.0000 Uiso H161 H 0.6476 0.9743 0.0774 0.0375 1.0000 Uiso H171 H 0.7341 0.9503 0.2866 0.0349 1.0000 Uiso H181 H 0.7419 0.6880 0.3843 0.0281 1.0000 Uiso 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 0.0159(8) 0.0135(7) 0.0186(8) 0.0011(8) 0.0020(6) 0.0002(8) C1 0.0181(9) 0.0176(9) 0.0178(9) 0.0018(10) 0.0023(7) 0.0014(10) C2 0.0224(11) 0.0220(11) 0.0255(11) 0.0089(9) 0.0059(9) 0.0009(9) C3 0.0207(12) 0.0175(10) 0.0315(13) 0.0049(9) 0.0061(10) 0.0005(9) C4 0.0205(12) 0.0157(10) 0.0216(11) -0.0015(9) 0.0040(9) 0.0007(9) C5 0.0199(11) 0.0201(10) 0.0212(11) 0.0035(9) 0.0041(9) 0.0001(9) O1 0.0299(8) 0.0322(10) 0.0252(8) -0.0051(7) 0.0098(6) -0.0016(7) O2 0.0169(8) 0.0309(9) 0.0289(8) -0.0030(7) 0.0067(7) -0.0048(7) C6 0.0147(11) 0.0406(14) 0.0352(13) 0.0025(11) 0.0079(10) 0.0002(10) C7 0.0263(13) 0.0420(15) 0.0351(14) 0.0045(11) 0.0117(11) -0.0022(11) C8 0.0176(11) 0.0190(10) 0.0164(10) 0.0014(9) 0.0031(8) 0.0030(8) O3 0.0236(8) 0.0161(7) 0.0265(9) -0.0014(7) -0.0017(7) -0.0002(7) O4 0.0207(8) 0.0165(7) 0.0230(8) 0.0004(6) -0.0025(6) 0.0036(6) C9 0.0210(11) 0.0213(11) 0.0293(12) 0.0025(9) -0.0021(9) 0.0069(9) C10 0.0294(14) 0.0359(14) 0.0499(17) -0.0003(13) -0.0144(12) 0.0046(11) C11 0.0284(14) 0.0343(14) 0.0426(16) -0.0031(11) 0.0099(12) 0.0079(11) C12 0.0357(15) 0.0291(13) 0.0327(13) 0.0100(11) 0.0015(11) 0.0047(11) S1 0.0171(2) 0.0160(2) 0.0246(2) 0.0022(2) 0.00303(18) 0.0016(2) O5 0.0305(10) 0.0175(8) 0.0354(10) -0.0014(7) 0.0144(8) 0.0036(7) O6 0.0192(7) 0.0328(8) 0.0352(8) 0.0116(10) -0.0056(6) 0.0006(9) C13 0.0172(11) 0.0173(10) 0.0223(10) 0.0017(9) 0.0049(9) 0.0001(8) C14 0.0232(12) 0.0213(11) 0.0220(11) -0.0024(9) 0.0068(9) -0.0011(9) C15 0.0324(13) 0.0306(13) 0.0248(12) 0.0065(10) 0.0095(10) 0.0078(10) C16 0.0345(12) 0.0205(10) 0.0389(12) 0.0068(12) 0.0119(10) -0.0031(12) C17 0.0285(12) 0.0186(12) 0.0402(13) -0.0017(11) 0.0036(10) -0.0014(10) C18 0.0196(11) 0.0220(11) 0.0285(12) -0.0015(9) 0.0024(9) -0.0011(9) _refine_ls_extinction_method None loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag N1 . C1 . 1.447(2) yes N1 . C4 . 1.466(3) yes N1 . C8 . 1.395(3) yes C1 . C2 . 1.539(3) yes C1 . S1 . 1.8191(19) yes C1 . H11 . 1.000 no C2 . C3 . 1.533(3) yes C2 . H21 . 1.000 no C2 . H22 . 1.000 no C3 . C4 . 1.540(3) yes C3 . H31 . 1.000 no C3 . H32 . 1.000 no C4 . C5 . 1.524(3) yes C4 . H41 . 1.000 no C5 . O1 . 1.205(3) yes C5 . O2 . 1.339(3) yes O2 . C6 . 1.470(3) yes C6 . C7 . 1.497(4) yes C6 . H61 . 1.000 no C6 . H62 . 1.000 no C7 . H71 . 1.000 no C7 . H72 . 1.000 no C7 . H73 . 1.000 no C8 . O3 . 1.198(3) yes C8 . O4 . 1.345(3) yes O4 . C9 . 1.488(3) yes C9 . C10 . 1.520(3) yes C9 . C11 . 1.512(3) yes C9 . C12 . 1.515(3) yes C10 . H101 . 1.000 no C10 . H102 . 1.000 no C10 . H103 . 1.000 no C11 . H111 . 1.000 no C11 . H112 . 1.000 no C11 . H113 . 1.000 no C12 . H121 . 1.000 no C12 . H122 . 1.000 no C12 . H123 . 1.000 no S1 . O5 . 1.4465(17) yes S1 . O6 . 1.4431(15) yes S1 . C13 . 1.760(2) yes C13 . C14 . 1.396(3) yes C13 . C18 . 1.382(3) yes C14 . C15 . 1.387(3) yes C14 . H141 . 1.000 no C15 . C16 . 1.393(4) yes C15 . H151 . 1.000 no C16 . C17 . 1.382(3) yes C16 . H161 . 1.000 no C17 . C18 . 1.395(3) yes C17 . H171 . 1.000 no C18 . H181 . 1.000 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 . N1 . C4 . 112.28(18) yes C1 . N1 . C8 . 117.34(18) yes C4 . N1 . C8 . 120.69(16) yes N1 . C1 . C2 . 105.24(18) yes N1 . C1 . S1 . 112.41(13) yes C2 . C1 . S1 . 108.63(15) yes N1 . C1 . H11 . 110.100 no C2 . C1 . H11 . 113.776 no S1 . C1 . H11 . 106.797 no C1 . C2 . C3 . 103.95(17) yes C1 . C2 . H21 . 110.835 no C3 . C2 . H21 . 110.835 no C1 . C2 . H22 . 110.835 no C3 . C2 . H22 . 110.834 no H21 . C2 . H22 . 109.467 no C2 . C3 . C4 . 103.34(18) yes C2 . C3 . H31 . 110.982 no C4 . C3 . H31 . 110.982 no C2 . C3 . H32 . 110.982 no C4 . C3 . H32 . 110.982 no H31 . C3 . H32 . 109.467 no N1 . C4 . C3 . 103.05(18) yes N1 . C4 . C5 . 109.71(17) yes C3 . C4 . C5 . 110.70(19) yes N1 . C4 . H41 . 113.861 no C3 . C4 . H41 . 112.921 no C5 . C4 . H41 . 106.634 no C4 . C5 . O1 . 124.0(2) yes C4 . C5 . O2 . 110.94(19) yes O1 . C5 . O2 . 125.0(2) yes C5 . O2 . C6 . 116.09(18) yes O2 . C6 . C7 . 112.2(2) yes O2 . C6 . H61 . 108.791 no C7 . C6 . H61 . 108.791 no O2 . C6 . H62 . 108.791 no C7 . C6 . H62 . 108.791 no H61 . C6 . H62 . 109.467 no C6 . C7 . H71 . 109.467 no C6 . C7 . H72 . 109.467 no H71 . C7 . H72 . 109.475 no C6 . C7 . H73 . 109.467 no H71 . C7 . H73 . 109.476 no H72 . C7 . H73 . 109.476 no N1 . C8 . O3 . 124.1(2) yes N1 . C8 . O4 . 108.31(17) yes O3 . C8 . O4 . 127.6(2) yes C8 . O4 . C9 . 119.92(16) yes O4 . C9 . C10 . 101.68(18) yes O4 . C9 . C11 . 109.29(18) yes C10 . C9 . C11 . 111.1(2) yes O4 . C9 . C12 . 109.47(18) yes C10 . C9 . C12 . 111.2(2) yes C11 . C9 . C12 . 113.4(2) yes C9 . C10 . H101 . 109.467 no C9 . C10 . H102 . 109.467 no H101 . C10 . H102 . 109.476 no C9 . C10 . H103 . 109.467 no H101 . C10 . H103 . 109.475 no H102 . C10 . H103 . 109.476 no C9 . C11 . H111 . 109.467 no C9 . C11 . H112 . 109.467 no H111 . C11 . H112 . 109.476 no C9 . C11 . H113 . 109.466 no H111 . C11 . H113 . 109.476 no H112 . C11 . H113 . 109.476 no C9 . C12 . H121 . 109.467 no C9 . C12 . H122 . 109.466 no H121 . C12 . H122 . 109.476 no C9 . C12 . H123 . 109.466 no H121 . C12 . H123 . 109.476 no H122 . C12 . H123 . 109.476 no C1 . S1 . O5 . 108.27(10) yes C1 . S1 . O6 . 105.37(9) yes O5 . S1 . O6 . 119.35(11) yes C1 . S1 . C13 . 106.11(11) yes O5 . S1 . C13 . 108.46(10) yes O6 . S1 . C13 . 108.53(11) yes S1 . C13 . C14 . 118.98(16) yes S1 . C13 . C18 . 119.37(17) yes C14 . C13 . C18 . 121.6(2) yes C13 . C14 . C15 . 118.8(2) yes C13 . C14 . H141 . 120.600 no C15 . C14 . H141 . 120.600 no C14 . C15 . C16 . 119.9(2) yes C14 . C15 . H151 . 120.025 no C16 . C15 . H151 . 120.025 no C15 . C16 . C17 . 120.7(2) yes C15 . C16 . H161 . 119.644 no C17 . C16 . H161 . 119.644 no C16 . C17 . C18 . 119.9(2) yes C16 . C17 . H171 . 120.050 no C18 . C17 . H171 . 120.050 no C13 . C18 . C17 . 119.0(2) yes C13 . C18 . H181 . 120.486 no C17 . C18 . H181 . 120.487 no