# Supplementary Material (ESI) for Perkin Transactions II # This journal is © The Royal Society of Chemistry, 1999 # CCDC Number: 188/173 data_pip2 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common '5-(N-piperidine)valeric acid dihydrate' _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C10 H23 N1 O4' _chemical_formula_weight 221.30 _chemical_melting_point ? _chemical_compound_source 'synthesized at Adam Mickiewicz University' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 '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' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M Pbca 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' '-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 16.008(3) _cell_length_b 15.932(3) _cell_length_c 9.647(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2460.4(8) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 55 _cell_measurement_theta_min 7 _cell_measurement_theta_max 22 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.195 _exptl_crystal_density_method ? _exptl_crystal_F_000 976 _exptl_absorpt_coefficient_mu 0.749 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device KUMA-4 _diffrn_measurement_method theta-2theta _diffrn_standards_number 2 _diffrn_standards_interval_count 100 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 2.04 _diffrn_reflns_number 1865 _diffrn_reflns_av_R_equivalents 0.0027 _diffrn_reflns_av_sigmaI/netI 0.0197 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_theta_min 5.53 _diffrn_reflns_theta_max 65.11 _reflns_number_total 1864 _reflns_number_observed 1525 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'KUMA software' _computing_cell_refinement KUMA _computing_data_reduction KUMA-DATAPROC _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics XP-Siemens _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.3108P)^2^+0.8976P] 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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0058(22) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 1864 _refine_ls_number_parameters 153 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0873 _refine_ls_R_factor_obs 0.0612 _refine_ls_wR_factor_all 0.2070 _refine_ls_wR_factor_obs 0.1973 _refine_ls_goodness_of_fit_all 1.100 _refine_ls_goodness_of_fit_obs 0.894 _refine_ls_restrained_S_all 1.105 _refine_ls_restrained_S_obs 0.901 _refine_ls_shift/esd_max 1.205 _refine_ls_shift/esd_mean 0.047 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group O1 O 0.3555(2) 0.4629(2) 0.3688(3) 0.0389(10) Uani 1 d . . O2 O 0.4548(2) 0.4852(2) 0.2143(3) 0.0415(10) Uani 1 d . . C5 C 0.4138(2) 0.4380(2) 0.2908(4) 0.0265(11) Uani 1 d . . C1 C 0.5942(3) 0.3278(3) 0.5926(4) 0.0348(11) Uani 1 d . . H1A H 0.5550(3) 0.3359(3) 0.6681(4) 0.042 Uiso 1 calc R . H1B H 0.6047(3) 0.2680(3) 0.5845(4) 0.042 Uiso 1 calc R . C2 C 0.5547(3) 0.3590(3) 0.4587(5) 0.0402(12) Uani 1 d . . H2A H 0.5474(3) 0.4194(3) 0.4639(5) 0.048 Uiso 1 calc R . H2B H 0.5918(3) 0.3470(3) 0.3818(5) 0.048 Uiso 1 calc R . C3 C 0.4705(2) 0.3177(2) 0.4327(5) 0.0350(11) Uani 1 d . . H3A H 0.4774(2) 0.2572(2) 0.4329(5) 0.042 Uiso 1 calc R . H3B H 0.4326(2) 0.3322(2) 0.5074(5) 0.042 Uiso 1 calc R . C4 C 0.4324(3) 0.3447(3) 0.2957(4) 0.0352(12) Uani 1 d . . H4A H 0.3810(3) 0.3137(3) 0.2806(4) 0.042 Uiso 1 calc R . H4B H 0.4706(3) 0.3306(3) 0.2211(4) 0.042 Uiso 1 calc R . N1 N 0.6737(2) 0.3712(2) 0.6268(3) 0.0268(10) Uani 1 d . . H1 H 0.6655(20) 0.4366(23) 0.6246(36) 0.009(8) Uiso 1 d . . C2' C 0.7036(3) 0.3499(3) 0.7705(4) 0.0356(12) Uani 1 d . . H2'1 H 0.6593(3) 0.3606(3) 0.8367(4) 0.043 Uiso 1 calc R . H2'2 H 0.7176(3) 0.2907(3) 0.7750(4) 0.043 Uiso 1 calc R . C3' C 0.7790(3) 0.4013(3) 0.8079(5) 0.0458(13) Uani 1 d . . H3'1 H 0.7978(3) 0.3858(3) 0.9000(5) 0.055 Uiso 1 calc R . H3'2 H 0.7637(3) 0.4602(3) 0.8098(5) 0.055 Uiso 1 calc R . C4' C 0.8498(3) 0.3887(3) 0.7056(5) 0.0424(13) Uani 1 d . . H4'1 H 0.8711(3) 0.3318(3) 0.7134(5) 0.051 Uiso 1 calc R . H4'2 H 0.8951(3) 0.4271(3) 0.7269(5) 0.051 Uiso 1 calc R . C5' C 0.8191(3) 0.4042(3) 0.5579(5) 0.0390(12) Uani 1 d . . H5'1 H 0.8063(3) 0.4633(3) 0.5467(5) 0.047 Uiso 1 calc R . H5'2 H 0.8631(3) 0.3900(3) 0.4930(5) 0.047 Uiso 1 calc R . C6' C 0.7422(3) 0.3530(3) 0.5246(4) 0.0319(11) Uani 1 d . . H6'1 H 0.7232(3) 0.3662(3) 0.4317(4) 0.038 Uiso 1 calc R . H6'2 H 0.7560(3) 0.2937(3) 0.5276(4) 0.038 Uiso 1 calc R . O1W O 0.7109(2) 0.1412(2) 0.6617(4) 0.0542(12) Uani 1 d D . H1W1 H 0.7099(42) 0.0815(10) 0.6284(58) 0.081 Uiso 1 d D . H1W2 H 0.6756(37) 0.1616(30) 0.5830(46) 0.081 Uiso 1 d D . O2W O 0.5619(2) 0.0912(2) 0.5240(4) 0.0513(12) Uani 1 d . . H2W1 H 0.5242(52) 0.0620(46) 0.6001(81) 0.082 Uiso 1 d . . H2W2 H 0.5644(50) 0.0631(53) 0.4706(78) 0.082 Uiso 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 O1 0.035(2) 0.034(2) 0.047(2) -0.0004(12) 0.0156(14) 0.0045(12) O2 0.043(2) 0.044(2) 0.037(2) 0.0044(13) 0.0119(14) -0.0052(13) C5 0.022(2) 0.034(2) 0.023(2) -0.002(2) -0.0084(15) 0.0019(15) C1 0.029(2) 0.039(2) 0.036(2) 0.005(2) -0.001(2) -0.002(2) C2 0.039(3) 0.043(3) 0.038(3) 0.007(2) -0.006(2) -0.001(2) C3 0.031(2) 0.032(2) 0.041(2) 0.005(2) -0.002(2) 0.002(2) C4 0.033(2) 0.034(2) 0.038(2) -0.005(2) -0.004(2) 0.001(2) N1 0.027(2) 0.035(2) 0.018(2) 0.0014(12) 0.0023(13) 0.0056(12) C2' 0.041(2) 0.048(2) 0.018(2) 0.008(2) 0.003(2) 0.011(2) C3' 0.046(3) 0.066(3) 0.026(2) -0.007(2) -0.011(2) 0.011(2) C4' 0.031(2) 0.051(3) 0.045(3) -0.001(2) -0.007(2) 0.004(2) C5' 0.038(2) 0.046(2) 0.033(3) 0.003(2) 0.006(2) -0.001(2) C6' 0.033(2) 0.045(2) 0.018(2) -0.0046(15) 0.007(2) 0.006(2) O1W 0.054(2) 0.057(2) 0.051(2) -0.017(2) -0.005(2) 0.004(2) O2W 0.044(2) 0.056(2) 0.054(3) -0.010(2) 0.015(2) -0.011(2) _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 C5 1.263(5) . ? O2 C5 1.241(5) . ? C5 C4 1.517(6) . ? C1 N1 1.486(5) . ? C1 C2 1.522(6) . ? C1 H1A 0.97 . ? C1 H1B 0.97 . ? C2 C3 1.520(6) . ? C2 H2A 0.97 . ? C2 H2B 0.97 . ? C3 C4 1.518(6) . ? C3 H3A 0.97 . ? C3 H3B 0.97 . ? C4 H4A 0.97 . ? C4 H4B 0.97 . ? N1 C6' 1.503(5) . ? N1 C2' 1.505(5) . ? N1 H1 1.05(4) . ? C2' C3' 1.503(7) . ? C2' H2'1 0.97 . ? C2' H2'2 0.97 . ? C3' C4' 1.517(7) . ? C3' H3'1 0.97 . ? C3' H3'2 0.97 . ? C4' C5' 1.528(6) . ? C4' H4'1 0.97 . ? C4' H4'2 0.97 . ? C5' C6' 1.511(6) . ? C5' H5'1 0.97 . ? C5' H5'2 0.97 . ? C6' H6'1 0.97 . ? C6' H6'2 0.97 . ? O1W H1W1 1.004(6) . ? O1W H1W2 1.000(2) . ? O2W H2W1 1.06(8) . ? O2W H2W2 0.68(8) . ? 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 O2 C5 O1 123.7(4) . . ? O2 C5 C4 120.6(4) . . ? O1 C5 C4 115.8(3) . . ? N1 C1 C2 113.1(3) . . ? N1 C1 H1A 109.0(2) . . ? C2 C1 H1A 109.0(2) . . ? N1 C1 H1B 109.0(2) . . ? C2 C1 H1B 109.0(2) . . ? H1A C1 H1B 107.8 . . ? C3 C2 C1 111.5(3) . . ? C3 C2 H2A 109.3(2) . . ? C1 C2 H2A 109.3(2) . . ? C3 C2 H2B 109.3(2) . . ? C1 C2 H2B 109.3(2) . . ? H2A C2 H2B 108.0 . . ? C4 C3 C2 112.2(3) . . ? C4 C3 H3A 109.2(2) . . ? C2 C3 H3A 109.2(2) . . ? C4 C3 H3B 109.2(2) . . ? C2 C3 H3B 109.2(2) . . ? H3A C3 H3B 107.9 . . ? C3 C4 C5 112.5(3) . . ? C3 C4 H4A 109.1(2) . . ? C5 C4 H4A 109.1(2) . . ? C3 C4 H4B 109.1(2) . . ? C5 C4 H4B 109.1(2) . . ? H4A C4 H4B 107.8 . . ? C1 N1 C6' 113.0(3) . . ? C1 N1 C2' 111.8(3) . . ? C6' N1 C2' 109.2(3) . . ? C1 N1 H1 110.5(18) . . ? C6' N1 H1 105.6(18) . . ? C2' N1 H1 106.4(19) . . ? C3' C2' N1 110.7(3) . . ? C3' C2' H2'1 109.5(2) . . ? N1 C2' H2'1 109.5(2) . . ? C3' C2' H2'2 109.5(2) . . ? N1 C2' H2'2 109.5(2) . . ? H2'1 C2' H2'2 108.1 . . ? C2' C3' C4' 111.8(4) . . ? C2' C3' H3'1 109.3(2) . . ? C4' C3' H3'1 109.2(2) . . ? C2' C3' H3'2 109.3(2) . . ? C4' C3' H3'2 109.3(3) . . ? H3'1 C3' H3'2 107.9 . . ? C3' C4' C5' 110.1(3) . . ? C3' C4' H4'1 109.6(3) . . ? C5' C4' H4'1 109.7(2) . . ? C3' C4' H4'2 109.6(3) . . ? C5' C4' H4'2 109.6(2) . . ? H4'1 C4' H4'2 108.1 . . ? C6' C5' C4' 111.9(4) . . ? C6' C5' H5'1 109.2(2) . . ? C4' C5' H5'1 109.2(2) . . ? C6' C5' H5'2 109.2(2) . . ? C4' C5' H5'2 109.2(2) . . ? H5'1 C5' H5'2 107.9 . . ? N1 C6' C5' 110.5(3) . . ? N1 C6' H6'1 109.5(2) . . ? C5' C6' H6'1 109.5(2) . . ? N1 C6' H6'2 109.5(2) . . ? C5' C6' H6'2 109.5(2) . . ? H6'1 C6' H6'2 108.1 . . ? H1W1 O1W H1W2 93.2(9) . . ? H2W1 O2W H2W2 105.6(81) . . ? 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 N1 C1 C2 C3 -175.9(3) . . . . ? C1 C2 C3 C4 -176.9(3) . . . . ? C2 C3 C4 C5 -62.9(5) . . . . ? O2 C5 C4 C3 110.8(4) . . . . ? O1 C5 C4 C3 -68.8(4) . . . . ? C2 C1 N1 C6' -66.1(4) . . . . ? C2 C1 N1 C2' 170.3(3) . . . . ? C1 N1 C2' C3' -174.1(3) . . . . ? C6' N1 C2' C3' 60.2(4) . . . . ? N1 C2' C3' C4' -57.8(5) . . . . ? C2' C3' C4' C5' 53.2(5) . . . . ? C3' C4' C5' C6' -52.8(5) . . . . ? C1 N1 C6' C5' 175.3(3) . . . . ? C2' N1 C6' C5' -59.6(4) . . . . ? C4' C5' C6' N1 56.8(4) . . . . ? _refine_diff_density_max 0.952 _refine_diff_density_min -1.068 _refine_diff_density_rms 0.218