# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2005 data_global _journal_coden_Cambridge 177 loop_ _publ_author_name 'Douglas W. Young' 'Heather M.E. Duggan' 'Peter B. Hitchcock' _publ_contact_author_name 'Prof Douglas W Young' _publ_contact_author_address ; Department of Chemistry University of Sussex Falmer, Brighton East Sussex, UK BN1 9QJ UNITED KINGDOM ; _publ_contact_author_email D.W.YOUNG@SUSSEX.AC.UK _publ_requested_journal 'Organic & Biomolecular Chemistry' _publ_section_title ; Synthesis of 5/7-, 5/8- and 5/9-Bicyclic Lactam Templates as Constraints for External b-Turns ; _publ_requested_category FO data_sep601 _database_code_depnum_ccdc_archive 'CCDC 265180' _audit_creation_date 2001-09-11T09:59:35-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.1 _audit_conform_dict_location ftp://ftp.iucr.org/cifdics/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety 'C10 H15 Cl1 N2 O3' _chemical_formula_sum 'C10 H15 Cl N2 O3' _chemical_formula_weight 246.69 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) _symmetry_Int_Tables_number 19 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 6.4839(4) _cell_length_b 12.5501(10) _cell_length_c 13.7734(7) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1120.79(13) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2984 _cell_measurement_theta_min 3.705 _cell_measurement_theta_max 25.028 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.05 _exptl_crystal_density_diffrn 1.462 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 520 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION NOT APPLIED # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.335 _exptl_absorpt_correction_T_min 0.8776 _exptl_absorpt_correction_T_max 0.9834 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_measurement_device KappaCCD _diffrn_measurement_method CCD _diffrn_reflns_number 4878 _diffrn_reflns_av_R_equivalents 0.0522 _diffrn_reflns_av_unetI/netI 0.0572 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.83 _diffrn_reflns_theta_max 25.04 _diffrn_reflns_theta_full 25.04 _diffrn_measured_fraction_theta_full 0.993 _diffrn_measured_fraction_theta_max 0.993 _reflns_number_total 1971 _reflns_number_gt 1735 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0265P)^2^+0.3393P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment 'refined isptropic' _refine_ls_extinction_method none _refine_ls_number_reflns 1971 _refine_ls_number_parameters 205 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0454 _refine_ls_R_factor_gt 0.0364 _refine_ls_wR_factor_ref 0.0802 _refine_ls_wR_factor_gt 0.076 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.02(8) _refine_diff_density_max 0.3 _refine_diff_density_min -0.187 _refine_diff_density_rms 0.044 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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' 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 Cl Cl 0.60909(11) 0.89568(5) 0.44091(5) 0.02711(19) Uani 1 1 d . . . O1 O 0.8303(3) 0.39474(16) 0.91089(14) 0.0341(5) Uani 1 1 d . . . O2 O 0.6622(3) 0.54729(15) 0.94023(16) 0.0349(5) Uani 1 1 d . . . H2A H 0.583(8) 0.496(4) 0.984(3) 0.120(18) Uiso 1 1 d . . . O3 O 0.6528(3) 0.55328(15) 0.70721(15) 0.0324(5) Uani 1 1 d . . . N1 N 0.5532(5) 0.7109(2) 0.58856(19) 0.0307(6) Uani 1 1 d . . . H1C H 0.428(6) 0.680(3) 0.612(2) 0.043(9) Uiso 1 1 d . . . H1B H 0.610(5) 0.664(3) 0.549(2) 0.040(9) Uiso 1 1 d . . . H1A H 0.526(5) 0.771(3) 0.559(3) 0.056(11) Uiso 1 1 d . . . N2 N 0.8935(4) 0.64672(15) 0.79158(15) 0.0212(5) Uani 1 1 d . . . C1 C 0.7475(4) 0.6366(2) 0.72283(19) 0.0223(6) Uani 1 1 d . . . C2 C 0.7028(4) 0.7384(2) 0.6664(2) 0.0215(6) Uani 1 1 d . . . H2 H 0.825(4) 0.761(2) 0.6344(17) 0.015(7) Uiso 1 1 d . . . C3 C 0.6254(5) 0.8283(2) 0.7287(2) 0.0251(6) Uani 1 1 d . . . H3 H 0.508(5) 0.857(2) 0.711(2) 0.031(8) Uiso 1 1 d . . . C4 C 0.7140(5) 0.8661(2) 0.8077(2) 0.0302(7) Uani 1 1 d . . . H4 H 0.655(5) 0.924(3) 0.836(2) 0.038(9) Uiso 1 1 d . . . C5 C 0.9121(5) 0.8313(2) 0.8543(2) 0.0341(7) Uani 1 1 d . . . H5B H 1.021(6) 0.901(3) 0.863(3) 0.072(12) Uiso 1 1 d . . . H5A H 0.875(4) 0.808(2) 0.920(2) 0.029(8) Uiso 1 1 d . . . C6 C 1.0258(4) 0.7415(2) 0.8038(2) 0.0264(6) Uani 1 1 d . . . H6 H 1.065(4) 0.765(2) 0.740(2) 0.026(7) Uiso 1 1 d . . . C7 C 1.2096(5) 0.6982(3) 0.8609(3) 0.0395(8) Uani 1 1 d . . . H7B H 1.307(6) 0.662(3) 0.811(3) 0.066(12) Uiso 1 1 d . . . H7A H 1.279(6) 0.754(3) 0.901(2) 0.053(10) Uiso 1 1 d . . . C8 C 1.1210(5) 0.6061(3) 0.9181(2) 0.0435(8) Uani 1 1 d . . . H8B H 1.033(5) 0.642(3) 0.983(3) 0.060(11) Uiso 1 1 d . . . H8A H 1.226(6) 0.551(3) 0.939(3) 0.057(10) Uiso 1 1 d . . . C9 C 0.9698(4) 0.5546(2) 0.8453(2) 0.0269(7) Uani 1 1 d . . . H9 H 1.033(4) 0.509(2) 0.801(2) 0.029(8) Uiso 1 1 d . . . C10 C 0.8117(5) 0.4909(2) 0.8997(2) 0.0288(7) 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 Cl 0.0306(4) 0.0213(3) 0.0295(3) -0.0005(3) 0.0001(3) 0.0003(3) O1 0.0445(13) 0.0199(10) 0.0380(11) 0.0053(9) 0.0072(9) 0.0010(10) O2 0.0375(13) 0.0258(11) 0.0414(12) 0.0038(11) 0.0126(11) 0.0043(9) O3 0.0339(13) 0.0223(11) 0.0409(11) 0.0004(9) -0.0034(9) -0.0074(9) N1 0.0401(17) 0.0245(14) 0.0275(14) 0.0023(13) -0.0085(12) -0.0049(13) N2 0.0237(11) 0.0169(11) 0.0231(11) 0.0039(9) 0.0005(10) 0.0010(10) C1 0.0240(14) 0.0194(14) 0.0235(14) 0.0001(12) 0.0060(11) 0.0002(12) C2 0.0224(14) 0.0198(14) 0.0222(14) 0.0011(12) -0.0021(12) -0.0042(12) C3 0.0247(15) 0.0191(14) 0.0315(16) 0.0050(12) 0.0014(13) 0.0026(13) C4 0.0416(18) 0.0213(16) 0.0278(16) -0.0051(13) 0.0026(13) 0.0052(13) C5 0.049(2) 0.0293(16) 0.0245(16) -0.0036(14) -0.0086(15) 0.0045(16) C6 0.0258(16) 0.0225(15) 0.0309(15) 0.0044(13) -0.0028(13) -0.0057(12) C7 0.0334(18) 0.037(2) 0.048(2) 0.0091(17) -0.0116(16) -0.0029(16) C8 0.0321(17) 0.0426(19) 0.056(2) 0.0159(17) -0.0160(16) -0.0037(19) C9 0.0251(15) 0.0223(15) 0.0334(16) 0.0078(14) 0.0043(13) 0.0064(12) C10 0.0329(17) 0.0260(17) 0.0274(15) 0.0034(13) -0.0045(13) 0.0013(13) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 O1 C10 1.222(3) . ? O2 C10 1.324(3) . ? O3 C1 1.231(3) . ? N1 C2 1.486(4) . ? N2 C1 1.345(4) . ? N2 C9 1.459(3) . ? N2 C6 1.476(3) . ? C1 C2 1.523(4) . ? C2 C3 1.504(4) . ? C3 C4 1.320(4) . ? C4 C5 1.501(4) . ? C5 C6 1.516(4) . ? C6 C7 1.528(4) . ? C7 C8 1.512(5) . ? C8 C9 1.545(4) . ? C9 C10 1.500(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N2 C9 121.4(2) . . ? C1 N2 C6 124.4(2) . . ? C9 N2 C6 112.6(2) . . ? O3 C1 N2 123.6(2) . . ? O3 C1 C2 121.9(2) . . ? N2 C1 C2 114.5(2) . . ? N1 C2 C3 111.6(3) . . ? N1 C2 C1 107.3(2) . . ? C3 C2 C1 113.7(2) . . ? C4 C3 C2 126.5(3) . . ? C3 C4 C5 128.3(3) . . ? C4 C5 C6 115.9(2) . . ? N2 C6 C5 111.6(2) . . ? N2 C6 C7 103.0(2) . . ? C5 C6 C7 114.0(3) . . ? C8 C7 C6 104.1(3) . . ? C7 C8 C9 102.8(2) . . ? N2 C9 C10 116.3(2) . . ? N2 C9 C8 102.3(2) . . ? C10 C9 C8 109.4(2) . . ? O1 C10 O2 123.1(3) . . ? O1 C10 C9 121.4(3) . . ? O2 C10 C9 115.2(3) . . ?