# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name _publ_author_address A.Sutherland ;WestCHEM, School of Chemistry, University Glasgow, Glasgow, G12 8QQ. ; L.Fowler ;WestCHEM, School of Chemistry, University Glasgow, Glasgow, G12 8QQ. ; L.Thomas ;Pfizer Ltd, Sandwich Kent CT13 9NJ ; D.Ellis ;WestCHEM, School of Chemistry, University Glasgow, Glasgow, G12 8QQ. ; # Name of author for correspondence _publ_contact_author_address ;WestCHEM, School of Chemistry University of Glasgow Glasgow G12 8QQ, UK ; # Address of author for correspondence _publ_contact_author_email Andrew.Sutherland@glasgow.ac.uk # SUBMISSION DETAILS _publ_contact_author_name 'Sutherland, Andrew' _publ_contact_letter ; Submission dated :2010-09-13 Please consider this CIF for submission to the Cambridge Crystallographic Data Centre. I certify that all authors have seen and approved of this submission, that all have made significant scientific contributions to the work reported, and that all share responsibility and accountability for the results. This CIF is submitted as part of a journal submission Org Lett Bloggs, Joe J. ; #============================================================================== # # TITLE AND AUTHOR LIST _publ_section_title ; Stereoselective Synthesis of 6-Substituted-4-Oxopipecolic Acids via a 6-endo-trig Cyclization ; data_lf01 _database_code_depnum_ccdc_archive 'CCDC 817525' #TrackingRef 'web_deposit_cif_file_0_LynneThomas_1300204414.cif' _audit_creation_date 2010-08-04T11:10:02-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _publ_section_title_footnote ; ? ; #============================================================================== # CHEMICAL DATA _chemical_name_systematic ; ? ; _chemical_formula_sum 'C7 H16 Cl N O4' _chemical_formula_weight 213.66 _chemical_absolute_configuration syn #============================================================================== # CRYSTAL DATA _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 8.2209(2) _cell_length_b 8.9923(3) _cell_length_c 13.8130(4) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1021.12(5) _cell_formula_units_Z 4 _cell_measurement_reflns_used 21495 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.878 _cell_measurement_temperature 100(2) _exptl_crystal_density_diffrn 1.39 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 456 _exptl_absorpt_coefficient_mu 0.36 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Blessing, 1997)' _exptl_absorpt_correction_T_min 0.5232 _exptl_absorpt_correction_T_max 0.7455 #============================================================================== # EXPERIMENTAL DATA _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD; rotation images' _diffrn_detector_area_resol_mean 9 _diffrn_reflns_number 8583 _diffrn_reflns_av_R_equivalents 0.0345 _diffrn_reflns_av_unetI/netI 0.0382 _diffrn_reflns_theta_min 2.7 _diffrn_reflns_theta_max 27.88 _diffrn_reflns_theta_full 27.88 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measured_fraction_theta_full 0.995 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 #============================================================================== # STRUCTURE SOLUTION _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #============================================================================== # REFINEMENT DATA _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^ > 2\s(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. ; _reflns_number_total 2418 _reflns_number_gt 2188 _reflns_threshold_expression >2\s(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0352 _refine_ls_R_factor_gt 0.0283 _refine_ls_wR_factor_ref 0.0639 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.057 _refine_ls_number_reflns 2418 _refine_ls_number_parameters 137 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0323P)^2^+0.0443P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.231 _refine_diff_density_min -0.161 _refine_diff_density_rms 0.041 _refine_ls_extinction_method none _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.10(5) 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 0 '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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' #============================================================================== # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol N1 0.73799(18) 0.68291(15) 0.62852(10) 0.0175(3) Uani d . 1 . . N H1 0.850(3) 0.6953(19) 0.6263(16) 0.038(6) Uiso d . 1 . . H H4 1.125(3) 0.698(2) 0.6627(17) 0.037(6) Uiso d . 1 . . H H2 0.695(2) 0.773(2) 0.6102(15) 0.031(5) Uiso d . 1 . . H H5 1.112(3) 0.632(2) 0.5756(18) 0.055(7) Uiso d . 1 . . H Cl1 0.11285(4) 0.48768(4) 0.42377(3) 0.02053(10) Uani d . 1 . . Cl O2 0.42111(12) 0.65916(12) 0.57185(9) 0.0234(2) Uani d . 1 . . O O3 0.47107(13) 0.46242(12) 0.47547(9) 0.0254(3) Uani d . 1 . . O H3A 0.3732 0.4674 0.4646 0.038 Uiso calc R 1 . . H O4 1.06679(14) 0.69491(14) 0.61434(10) 0.0243(3) Uani d . 1 . . O O1 0.77050(15) 0.23798(12) 0.71765(9) 0.0243(3) Uani d . 1 . . O H1A 0.7301 0.1702 0.686 0.036 Uiso calc R 1 . . H C6 0.51323(18) 0.56946(18) 0.53647(12) 0.0192(3) Uani d . 1 . . C C2 0.76036(18) 0.41521(16) 0.58570(12) 0.0182(3) Uani d . 1 . . C H2A 0.7227 0.34 0.5406 0.022 Uiso calc R 1 . . H H2B 0.8783 0.416 0.5841 0.022 Uiso calc R 1 . . H C4 0.7556(2) 0.49450(19) 0.75930(11) 0.0204(3) Uani d . 1 . . C H4A 0.8735 0.4977 0.7618 0.024 Uiso calc R 1 . . H H4B 0.7162 0.4684 0.8233 0.024 Uiso calc R 1 . . H C3 0.70276(19) 0.37618(17) 0.68740(12) 0.0195(3) Uani d . 1 . . C H3B 0.5838 0.3688 0.6877 0.023 Uiso calc R 1 . . H C1 0.69606(18) 0.56750(17) 0.55454(11) 0.0173(3) Uani d . 1 . . C H1B 0.7503 0.5946 0.4939 0.021 Uiso calc R 1 . . H C7 0.7569(2) 0.76941(19) 0.79732(13) 0.0255(4) Uani d . 1 . . C H7A 0.8736 0.7659 0.7976 0.038 Uiso calc R 1 . . H H7B 0.717 0.7548 0.8619 0.038 Uiso calc R 1 . . H H7C 0.7215 0.8645 0.7738 0.038 Uiso calc R 1 . . H C5 0.69112(19) 0.64714(17) 0.73172(12) 0.0201(3) Uani d . 1 . . C H5A 0.5722 0.646 0.7366 0.024 Uiso calc R 1 . . H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 N1 0.0161(7) 0.0182(7) 0.0182(8) -0.0001(6) -0.0008(6) -0.0007(5) Cl1 0.01916(16) 0.02000(17) 0.02243(19) -0.00164(16) -0.00062(16) -0.00253(16) O2 0.0192(5) 0.0258(5) 0.0253(6) 0.0014(4) -0.0001(5) -0.0040(5) O3 0.0196(5) 0.0266(6) 0.0300(7) 0.0017(5) -0.0068(5) -0.0078(5) O4 0.0205(7) 0.0311(7) 0.0212(7) 0.0012(5) -0.0007(5) -0.0054(5) O1 0.0330(7) 0.0186(5) 0.0213(7) 0.0003(5) -0.0053(5) 0.0005(5) C6 0.0199(7) 0.0208(7) 0.0167(8) -0.0016(7) -0.0018(6) 0.0025(6) C2 0.0189(7) 0.0192(7) 0.0165(8) -0.0007(6) -0.0010(7) -0.0014(6) C4 0.0223(7) 0.0230(7) 0.0158(7) -0.0006(7) -0.0002(6) 0.0006(7) C3 0.0205(8) 0.0194(8) 0.0185(9) 0.0006(6) -0.0011(6) 0.0006(6) C1 0.0176(7) 0.0197(7) 0.0146(9) -0.0009(6) 0.0006(6) -0.0005(6) C7 0.0265(9) 0.0272(9) 0.0227(10) 0.0039(8) -0.0026(7) -0.0053(7) C5 0.0190(8) 0.0251(8) 0.0162(8) 0.0008(7) -0.0004(6) -0.0005(7) #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag N1 C1 . 1.4967(19) ? N1 C5 . 1.511(2) ? N1 H1 . 0.93(2) ? N1 H2 . 0.92(2) ? O2 C6 . 1.2095(19) ? O3 C6 . 1.3253(19) ? O3 H3A . 0.82 ? O4 H4 . 0.82(2) ? O4 H5 . 0.86(2) ? O1 C3 . 1.4245(19) ? O1 H1A . 0.82 ? C6 C1 . 1.5237(19) ? C2 C3 . 1.524(2) ? C2 C1 . 1.530(2) ? C2 H2A . 0.97 ? C2 H2B . 0.97 ? C4 C3 . 1.519(2) ? C4 C5 . 1.520(2) ? C4 H4A . 0.97 ? C4 H4B . 0.97 ? C3 H3B . 0.98 ? C1 H1B . 0.98 ? C7 C5 . 1.524(2) ? C7 H7A . 0.96 ? C7 H7B . 0.96 ? C7 H7C . 0.96 ? C5 H5A . 0.98 ? 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 115.96(12) . . ? C1 N1 H1 106.8(12) . . ? C5 N1 H1 108.0(13) . . ? C1 N1 H2 109.4(13) . . ? C5 N1 H2 110.4(13) . . ? H1 N1 H2 105.6(17) . . ? C6 O3 H3A 109.5 . . ? H4 O4 H5 105.9(19) . . ? C3 O1 H1A 109.5 . . ? O2 C6 O3 125.27(14) . . ? O2 C6 C1 124.00(14) . . ? O3 C6 C1 110.71(13) . . ? C3 C2 C1 110.99(12) . . ? C3 C2 H2A 109.4 . . ? C1 C2 H2A 109.4 . . ? C3 C2 H2B 109.4 . . ? C1 C2 H2B 109.4 . . ? H2A C2 H2B 108 . . ? C3 C4 C5 111.65(13) . . ? C3 C4 H4A 109.3 . . ? C5 C4 H4A 109.3 . . ? C3 C4 H4B 109.3 . . ? C5 C4 H4B 109.3 . . ? H4A C4 H4B 108 . . ? O1 C3 C4 107.91(13) . . ? O1 C3 C2 110.48(13) . . ? C4 C3 C2 110.65(13) . . ? O1 C3 H3B 109.3 . . ? C4 C3 H3B 109.3 . . ? C2 C3 H3B 109.3 . . ? N1 C1 C6 109.33(13) . . ? N1 C1 C2 110.43(12) . . ? C6 C1 C2 113.41(13) . . ? N1 C1 H1B 107.8 . . ? C6 C1 H1B 107.8 . . ? C2 C1 H1B 107.8 . . ? C5 C7 H7A 109.5 . . ? C5 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C5 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N1 C5 C4 109.86(13) . . ? N1 C5 C7 108.48(13) . . ? C4 C5 C7 112.26(14) . . ? N1 C5 H5A 108.7 . . ? C4 C5 H5A 108.7 . . ? C7 C5 H5A 108.7 . . ? 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 C5 C4 C3 O1 178.98(13) . . . . ? C5 C4 C3 C2 58.00(17) . . . . ? C1 C2 C3 O1 -176.85(12) . . . . ? C1 C2 C3 C4 -57.40(17) . . . . ? C5 N1 C1 C6 73.61(17) . . . . ? C5 N1 C1 C2 -51.84(17) . . . . ? O2 C6 C1 N1 5.2(2) . . . . ? O3 C6 C1 N1 -176.29(12) . . . . ? O2 C6 C1 C2 128.87(16) . . . . ? O3 C6 C1 C2 -52.59(18) . . . . ? C3 C2 C1 N1 53.26(16) . . . . ? C3 C2 C1 C6 -69.84(16) . . . . ? C1 N1 C5 C4 51.76(17) . . . . ? C1 N1 C5 C7 174.81(13) . . . . ? C3 C4 C5 N1 -53.49(17) . . . . ? C3 C4 C5 C7 -174.29(13) . . . . ? # The following lines are used to test the character set of files sent by # network email or other means. They are not part of the CIF data set # abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789 # !@#$%^&*()_+{}:"~<>?|\-=[];'`,./ # END of CIF