# Supplementary Material (ESI) for ChemComm # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 182/1800 data_global # 1. SUBMISSION DETAILS _publ_contact_author_name 'Prof. Alajos Kalman' _publ_contact_author_address ; Institute of Chemistry, Chemical Research Center Hungarian Academy of Sciences PO Box 17 H-1525 Budapest Hungary ; _publ_contact_author_phone '036 1 325-7547' _publ_contact_author_fax '036 1 325-7554' _publ_contact_author_email 'akalman@cric.chemres.hu' _publ_requested_journal 'Chemical Communications' _publ_requested_coeditor_name ? _publ_contact_letter ; This is the supplementary crystallographic file for crystal structures a, b and c. Manuscript sent to "Chemical Communications". We are waiting your answer and the CCDC supplementary publication number for structure a(bs14n), b(bg29n) and c(bg1cn) Yours sincerely, Alajos K\'alm\'an ; #============================================================================== # 3. TITLE AND AUTHOR LIST _publ_section_title ; Supramolecular similarities between a diastereomer pair and their truncated derivative: common tetrameric synthon and isostructurality ; loop_ _publ_author_name _publ_author_address 'K\'alm\'an, Alajos' ; Institute of Chemistry, Chemical Research Center Hungarian Academy of Sciences PO Box 17 H-1525 Budapest Hungary ; 'F\'abi\'an, L\'aszl\'o' ; Institute of Chemistry, Chemical Research Center Hungarian Academy of Sciences PO Box 17 H-1525 Budapest Hungary ; 'Argay, Gyula' ; Institute of Chemistry, Chemical Research Center Hungarian Academy of Sciences PO Box 17 H-1525 Budapest Hungary ; #============================================================================== # 4. TEXT _publ_section_abstract ; A common tetrameric supramolecular synthon and an unexpected isostructurality reveal similarities between the crystal structures of tree related cyclopentane derivatives fused together by OH...O and NH...O hydrogen bonds ; _publ_section_comment ; ? ; _publ_section_experimental ; ? ; _publ_section_references ; ? ; _publ_section_figure_captions ; ? ; _publ_section_acknowledgements ; ? ; #============================================================================== data_a _audit_creation_method SHELXL-97 _chemical_name_systematic # name for 4 (bs14n) =A in Chem.Commun. paper ; (1R*,2S*,4R*)-4-tert-butyl-2-hydroxy-1-cyclopentanecarboxylic acid ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H18 O3' _chemical_formula_weight 186.24 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' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.931(1) _cell_length_b 6.200(1) _cell_length_c 15.951(3) _cell_angle_alpha 84.30(4) _cell_angle_beta 89.97(4) _cell_angle_gamma 62.28(4) _cell_volume 515.97(15) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 11.0 _cell_measurement_theta_max 13.2 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.199 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 204 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.9661 _exptl_absorpt_correction_T_max 0.9922 _exptl_absorpt_process_details 'North A.C., Philips, D.C. & Mathews, F.(1968) Acta Cryst. A24, 350-359.' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf-Nonius CAD4' _diffrn_measurement_method '\w--2\q' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 _diffrn_standards_decay_% ? _diffrn_reflns_number 2998 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0277 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.57 _diffrn_reflns_theta_max 29.95 _reflns_number_total 2998 _reflns_number_gt 1971 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4 Express' _computing_cell_refinement 'CAD4 Express' _computing_data_reduction 'XCAD4 (Harms 1996)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLUTO in CSD(Allen F.H & Kennard O.(1993))' _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^)+(0.0626P)^2^+0.1708P] 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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.029(11) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2998 _refine_ls_number_parameters 124 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0910 _refine_ls_R_factor_gt 0.0477 _refine_ls_wR_factor_ref 0.1776 _refine_ls_wR_factor_gt 0.1249 _refine_ls_goodness_of_fit_ref 1.147 _refine_ls_restrained_S_all 1.147 _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 0.7882(3) 0.3707(3) 0.36328(11) 0.0474(4) Uani 1 1 d . . . H1 H 0.7288 0.2469 0.3703 0.062 Uiso 1 1 calc R . . C2 C 0.5662(3) 0.6158(3) 0.38003(10) 0.0463(4) Uani 1 1 d . . . H2 H 0.4813 0.5987 0.4311 0.060 Uiso 1 1 calc R . . C3 C 0.3899(3) 0.6885(3) 0.30148(11) 0.0495(4) Uani 1 1 d . . . H3A H 0.3063 0.8651 0.2873 0.064 Uiso 1 1 calc R . . H3B H 0.2601 0.6365 0.3110 0.064 Uiso 1 1 calc R . . C4 C 0.5580(3) 0.5598(3) 0.22890(10) 0.0460(4) Uani 1 1 d . . . H4 H 0.5043 0.4409 0.2134 0.060 Uiso 1 1 calc R . . C5 C 0.8292(3) 0.4107(3) 0.27038(11) 0.0571(5) Uani 1 1 d . . . H5A H 0.9200 0.2553 0.2473 0.074 Uiso 1 1 calc R . . H5B H 0.9253 0.5011 0.2618 0.074 Uiso 1 1 calc R . . C6 C 1.0209(3) 0.2834(2) 0.42122(11) 0.0458(4) Uani 1 1 d . . . C7 C 0.5363(3) 0.7255(3) 0.14759(11) 0.0498(4) Uani 1 1 d . . . C8 C 0.7260(4) 0.5711(5) 0.08542(14) 0.0751(6) Uani 1 1 d . . . H8A H 0.7034 0.6706 0.0329 0.113 Uiso 1 1 calc R . . H8B H 0.6964 0.4355 0.0761 0.113 Uiso 1 1 calc R . . H8C H 0.8969 0.5104 0.1084 0.113 Uiso 1 1 calc R . . C9 C 0.2666(4) 0.8324(4) 0.10708(13) 0.0669(5) Uani 1 1 d . . . H9A H 0.2361 0.7016 0.0922 0.100 Uiso 1 1 calc R . . H9B H 0.2502 0.9402 0.0573 0.100 Uiso 1 1 calc R . . H9C H 0.1445 0.9223 0.1464 0.100 Uiso 1 1 calc R . . C10 C 0.5879(5) 0.9360(4) 0.16529(16) 0.0689(6) Uani 1 1 d . . . H10A H 0.5835 1.0294 0.1130 0.103 Uiso 1 1 calc R . . H10B H 0.7528 0.8713 0.1936 0.103 Uiso 1 1 calc R . . H10C H 0.4597 1.0399 0.2004 0.103 Uiso 1 1 calc R . . O1 O 0.6676(2) 0.7837(2) 0.38681(8) 0.0512(3) Uani 1 1 d . . . H1A H 0.5509 0.9198 0.3927 0.067 Uiso 1 1 calc R . . O2 O 1.2327(2) 0.2288(2) 0.39724(9) 0.0587(4) Uani 1 1 d . . . O3 O 0.9693(2) 0.2736(2) 0.50166(8) 0.0525(3) Uani 1 1 d . . . H3C H 1.0925 0.2539 0.5309 0.068 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 C1 0.0436(8) 0.0361(7) 0.0557(9) -0.0037(6) -0.0028(6) -0.0133(6) C2 0.0362(7) 0.0475(8) 0.0454(8) -0.0016(6) 0.0045(5) -0.0120(6) C3 0.0384(7) 0.0520(9) 0.0521(9) -0.0038(7) 0.0024(6) -0.0165(6) C4 0.0469(8) 0.0389(7) 0.0507(8) -0.0085(6) -0.0011(6) -0.0182(6) C5 0.0481(9) 0.0483(9) 0.0520(9) -0.0163(7) 0.0031(7) -0.0014(7) C6 0.0429(7) 0.0263(6) 0.0565(9) -0.0052(6) 0.0009(6) -0.0064(5) C7 0.0469(8) 0.0501(9) 0.0502(8) -0.0074(7) 0.0037(6) -0.0203(7) C8 0.0714(13) 0.0813(15) 0.0585(11) -0.0173(10) 0.0121(10) -0.0221(12) C9 0.0584(11) 0.0728(13) 0.0583(11) -0.0004(9) -0.0072(8) -0.0225(10) C10 0.0745(13) 0.0591(11) 0.0808(14) -0.0024(10) 0.0112(11) -0.0386(10) O1 0.0387(6) 0.0374(6) 0.0614(7) -0.0114(5) -0.0034(5) -0.0032(4) O2 0.0404(6) 0.0468(7) 0.0698(8) -0.0112(6) 0.0041(5) -0.0035(5) O3 0.0493(6) 0.0468(6) 0.0537(7) 0.0012(5) -0.0038(5) -0.0172(5) _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 C6 1.503(2) . ? C1 C5 1.516(3) . ? C1 C2 1.527(2) . ? C2 O1 1.436(2) . ? C2 C3 1.522(2) . ? C3 C4 1.554(2) . ? C4 C7 1.538(2) . ? C4 C5 1.541(2) . ? C6 O2 1.212(2) . ? C6 O3 1.321(2) . ? C7 C10 1.523(3) . ? C7 C9 1.531(3) . ? C7 C8 1.533(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 C6 C1 C5 115.18(15) . . ? C6 C1 C2 114.76(14) . . ? C5 C1 C2 103.37(14) . . ? O1 C2 C3 111.47(14) . . ? O1 C2 C1 107.25(12) . . ? C3 C2 C1 103.32(14) . . ? C2 C3 C4 107.04(13) . . ? C7 C4 C5 115.09(15) . . ? C7 C4 C3 116.37(14) . . ? C5 C4 C3 104.57(13) . . ? C1 C5 C4 104.55(14) . . ? O2 C6 O3 123.41(16) . . ? O2 C6 C1 124.04(16) . . ? O3 C6 C1 112.55(14) . . ? C10 C7 C9 108.72(17) . . ? C10 C7 C8 109.87(18) . . ? C9 C7 C8 108.30(16) . . ? C10 C7 C4 111.62(15) . . ? C9 C7 C4 109.08(15) . . ? C8 C7 C4 109.17(16) . . ? 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 C6 C1 C2 O1 48.47(18) . . . . ? C5 C1 C2 O1 -77.77(16) . . . . ? C6 C1 C2 C3 166.34(14) . . . . ? C5 C1 C2 C3 40.09(17) . . . . ? O1 C2 C3 C4 89.62(16) . . . . ? C1 C2 C3 C4 -25.25(17) . . . . ? C2 C3 C4 C7 -126.96(15) . . . . ? C2 C3 C4 C5 1.20(18) . . . . ? C6 C1 C5 C4 -165.72(13) . . . . ? C2 C1 C5 C4 -39.75(17) . . . . ? C7 C4 C5 C1 152.56(15) . . . . ? C3 C4 C5 C1 23.63(18) . . . . ? C5 C1 C6 O2 -5.6(2) . . . . ? C2 C1 C6 O2 -125.45(17) . . . . ? C5 C1 C6 O3 174.09(14) . . . . ? C2 C1 C6 O3 54.21(19) . . . . ? C5 C4 C7 C10 -67.9(2) . . . . ? C3 C4 C7 C10 54.9(2) . . . . ? C5 C4 C7 C9 171.94(15) . . . . ? C3 C4 C7 C9 -65.22(19) . . . . ? C5 C4 C7 C8 53.8(2) . . . . ? C3 C4 C7 C8 176.60(15) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O3 H3C O1 0.82 1.85 2.664(2) 169.5 2_766 O1 H1A O2 0.82 1.97 2.786(2) 170.2 1_465 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 29.95 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.300 _refine_diff_density_min -0.268 _refine_diff_density_rms 0.053 # end of a(bs14n) # =================================================================== data_b _audit_creation_method SHELXL-97 _chemical_name_systematic # name for 5 (bg29n) =B in Chem.Commun. paper ; (1S*,2R*,4R*)-4-tert-butyl-2-hydroxy-1-cyclopentanecarboxylic acid ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H18 O3' _chemical_formula_weight 186.24 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' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y+1/2, z+1/2' '-x, -y, -z' '-x, y-1/2, -z-1/2' _cell_length_a 16.862(2) _cell_length_b 6.104(1) _cell_length_c 10.519(3) _cell_angle_alpha 90.00 _cell_angle_beta 107.03(4) _cell_angle_gamma 90.00 _cell_volume 1035.2(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 24.50 _cell_measurement_theta_max 28.30 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.195 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 408 _exptl_absorpt_coefficient_mu 0.704 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.7913 _exptl_absorpt_correction_T_max 0.9374 _exptl_absorpt_process_details 'North A.C., Philips, D.C. & Mathews, F.(1968) Acta Cryst. A24, 350-359.' _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_type 'Enraf-Nonius CAD4' _diffrn_measurement_method '\w--2\q' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 _diffrn_standards_decay_% ? _diffrn_reflns_number 2084 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0337 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.74 _diffrn_reflns_theta_max 74.99 _reflns_number_total 2084 _reflns_number_gt 1598 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4 Express' _computing_cell_refinement 'CAD4 Express' _computing_data_reduction 'XCAD4 (Harms 1996)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLUTO in CSD(Allen F.H & Kennard O.(1993))' _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^)+(0.1017P)^2^+0.4219P] 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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0019(9) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2084 _refine_ls_number_parameters 125 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0732 _refine_ls_R_factor_gt 0.0541 _refine_ls_wR_factor_ref 0.1688 _refine_ls_wR_factor_gt 0.1415 _refine_ls_goodness_of_fit_ref 0.951 _refine_ls_restrained_S_all 0.951 _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 0.35505(10) -0.0958(3) 0.58254(16) 0.0398(4) Uani 1 1 d . . . H1 H 0.3505 -0.2480 0.5516 0.052 Uiso 1 1 calc R . . C2 C 0.38233(10) 0.0392(3) 0.48141(16) 0.0418(4) Uani 1 1 d . . . H2 H 0.4286 -0.0295 0.4577 0.054 Uiso 1 1 calc R . . C3 C 0.30370(10) 0.0451(3) 0.36427(16) 0.0443(4) Uani 1 1 d . . . H3A H 0.2980 -0.0888 0.3127 0.058 Uiso 1 1 calc R . . H3B H 0.3047 0.1685 0.3067 0.058 Uiso 1 1 calc R . . C4 C 0.23157(10) 0.0685(3) 0.42660(16) 0.0412(4) Uani 1 1 d . . . H4 H 0.2209 0.2255 0.4323 0.054 Uiso 1 1 calc R . . C5 C 0.26735(11) -0.0175(4) 0.57051(17) 0.0505(5) Uani 1 1 d . . . H5A H 0.2684 0.0984 0.6341 0.066 Uiso 1 1 calc R . . H5B H 0.2339 -0.1372 0.5870 0.066 Uiso 1 1 calc R . . C6 C 0.41419(10) -0.0947(2) 0.72128(16) 0.0398(4) Uani 1 1 d . . . C7 C 0.14966(10) -0.0382(3) 0.34636(18) 0.0455(4) Uani 1 1 d . . . C8 C 0.08188(13) 0.0187(5) 0.4114(3) 0.0735(7) Uani 1 1 d . . . H8A H 0.0971 -0.0374 0.5005 0.096 Uiso 1 1 calc R . . H8B H 0.0303 -0.0457 0.3609 0.096 Uiso 1 1 calc R . . H8C H 0.0758 0.1749 0.4133 0.096 Uiso 1 1 calc R . . C9 C 0.12460(14) 0.0530(4) 0.2045(2) 0.0672(6) Uani 1 1 d . . . H9A H 0.1214 0.2099 0.2074 0.087 Uiso 1 1 calc R . . H9B H 0.0715 -0.0052 0.1558 0.087 Uiso 1 1 calc R . . H9C H 0.1652 0.0116 0.1613 0.087 Uiso 1 1 calc R . . C10 C 0.15631(15) -0.2882(4) 0.3396(2) 0.0633(6) Uani 1 1 d . . . H10A H 0.1670 -0.3486 0.4273 0.082 Uiso 1 1 calc R . . H10B H 0.2009 -0.3260 0.3042 0.082 Uiso 1 1 calc R . . H10C H 0.1052 -0.3465 0.2832 0.082 Uiso 1 1 calc R . . O1 O 0.40347(9) 0.2564(2) 0.53654(13) 0.0551(4) Uani 1 1 d . . . H1A H 0.4067 0.3406 0.4775 0.092(10) Uiso 1 1 calc R . . O2 O 0.39432(8) -0.0464(2) 0.81974(12) 0.0499(4) Uani 1 1 d . . . O3 O 0.48924(8) -0.1578(3) 0.72425(13) 0.0553(4) Uani 1 1 d . . . H3C H 0.5182 -0.1672 0.8017 0.072 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 C1 0.0458(9) 0.0366(8) 0.0393(8) -0.0004(6) 0.0158(6) 0.0000(6) C2 0.0389(8) 0.0466(9) 0.0418(8) -0.0009(7) 0.0146(6) -0.0051(6) C3 0.0413(9) 0.0524(10) 0.0390(8) 0.0022(7) 0.0116(7) -0.0075(7) C4 0.0401(8) 0.0361(8) 0.0476(9) -0.0060(6) 0.0130(7) 0.0011(6) C5 0.0420(9) 0.0697(12) 0.0429(9) -0.0028(8) 0.0175(7) -0.0001(8) C6 0.0452(8) 0.0302(7) 0.0440(8) 0.0045(6) 0.0131(7) 0.0015(6) C7 0.0378(8) 0.0484(10) 0.0497(9) -0.0043(7) 0.0118(7) -0.0005(7) C8 0.0407(10) 0.1004(19) 0.0809(15) -0.0118(13) 0.0201(10) 0.0053(10) C9 0.0544(11) 0.0800(15) 0.0573(12) 0.0064(11) 0.0010(9) -0.0032(10) C10 0.0732(13) 0.0489(11) 0.0717(13) -0.0091(9) 0.0275(11) -0.0159(9) O1 0.0626(8) 0.0488(8) 0.0475(7) 0.0053(6) 0.0062(6) -0.0195(6) O2 0.0573(7) 0.0515(7) 0.0423(6) -0.0008(5) 0.0169(5) 0.0009(6) O3 0.0528(7) 0.0614(9) 0.0488(7) 0.0044(6) 0.0105(6) 0.0201(6) _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 C6 1.507(2) . ? C1 C2 1.519(2) . ? C1 C5 1.524(2) . ? C2 O1 1.449(2) . ? C2 C3 1.523(2) . ? C3 C4 1.548(2) . ? C4 C7 1.537(2) . ? C4 C5 1.548(2) . ? C6 O2 1.215(2) . ? C6 O3 1.314(2) . ? C7 C9 1.532(3) . ? C7 C10 1.533(3) . ? C7 C8 1.534(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 C6 C1 C2 115.17(14) . . ? C6 C1 C5 115.45(14) . . ? C2 C1 C5 104.90(14) . . ? O1 C2 C1 107.78(13) . . ? O1 C2 C3 110.85(14) . . ? C1 C2 C3 102.06(13) . . ? C2 C3 C4 105.38(13) . . ? C7 C4 C5 115.05(15) . . ? C7 C4 C3 114.80(14) . . ? C5 C4 C3 104.68(13) . . ? C1 C5 C4 106.16(13) . . ? O2 C6 O3 123.71(16) . . ? O2 C6 C1 123.86(15) . . ? O3 C6 C1 112.40(14) . . ? C9 C7 C10 108.66(18) . . ? C9 C7 C8 108.84(18) . . ? C10 C7 C8 108.68(18) . . ? C9 C7 C4 109.14(16) . . ? C10 C7 C4 112.41(16) . . ? C8 C7 C4 109.04(16) . . ? 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 C6 C1 C2 O1 -51.46(18) . . . . ? C5 C1 C2 O1 76.59(16) . . . . ? C6 C1 C2 C3 -168.25(14) . . . . ? C5 C1 C2 C3 -40.19(17) . . . . ? O1 C2 C3 C4 -76.09(16) . . . . ? C1 C2 C3 C4 38.46(17) . . . . ? C2 C3 C4 C7 -149.25(14) . . . . ? C2 C3 C4 C5 -22.15(18) . . . . ? C6 C1 C5 C4 154.62(14) . . . . ? C2 C1 C5 C4 26.74(18) . . . . ? C7 C4 C5 C1 124.19(15) . . . . ? C3 C4 C5 C1 -2.76(18) . . . . ? C2 C1 C6 O2 126.22(18) . . . . ? C5 C1 C6 O2 3.6(2) . . . . ? C2 C1 C6 O3 -55.56(19) . . . . ? C5 C1 C6 O3 -178.13(16) . . . . ? C5 C4 C7 C9 -176.78(16) . . . . ? C3 C4 C7 C9 -55.2(2) . . . . ? C5 C4 C7 C10 -56.1(2) . . . . ? C3 C4 C7 C10 65.5(2) . . . . ? C5 C4 C7 C8 64.4(2) . . . . ? C3 C4 C7 C8 -173.95(17) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O3 H3C O1 0.82 1.88 2.686(2) 166.3 4_657 O1 H1A O2 0.82 2.04 2.8550(19) 170.8 2_554 _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 74.99 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 0.249 _refine_diff_density_min -0.241 _refine_diff_density_rms 0.053 # end of b(bg29n) # ================================================================ data_c _audit_creation_method SHELXL-97 _chemical_name_systematic # name for 1 (bg1cn) =C in Chem.Commun. paper ; cis(1R*,2S*)-2-hydroxy-1-cyclopentanecarboxamide ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H11 N1 O2' _chemical_formula_weight 129.16 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 monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.693(2) _cell_length_b 7.225(1) _cell_length_c 7.902(2) _cell_angle_alpha 90.00 _cell_angle_beta 103.70(3) _cell_angle_gamma 90.00 _cell_volume 648.6(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 26.08 _cell_measurement_theta_max 29.89 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.323 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 280 _exptl_absorpt_coefficient_mu 0.819 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.7913 _exptl_absorpt_correction_T_max 0.9374 _exptl_absorpt_process_details 'North A.C., Philips, D.C. & Mathews, F.(1968) Acta Cryst. A24, 350-359.' _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_type 'Enraf-Nonius CAD4' _diffrn_measurement_method '\w--2\q' _diffrn_refln_scan_width 0.46+0.22tg(theta) _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 2 _diffrn_reflns_number 1431 _diffrn_reflns_av_R_equivalents 0.0170 _diffrn_reflns_av_sigmaI/netI 0.0135 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.89 _diffrn_reflns_theta_max 74.91 _reflns_number_total 1274 _reflns_number_gt 1149 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4 Express' _computing_cell_refinement 'CAD4 Express' _computing_data_reduction 'XCAD4 (Harms 1996)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLUTO in CSD(Allen F.H & Kennard O.(1993))' _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^)+(0.1000P)^2^+0.0000P] 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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.026(5) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 1274 _refine_ls_number_parameters 84 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0437 _refine_ls_R_factor_gt 0.0406 _refine_ls_wR_factor_ref 0.1272 _refine_ls_wR_factor_gt 0.1238 _refine_ls_goodness_of_fit_ref 1.138 _refine_ls_restrained_S_all 1.138 _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 0.23443(9) 0.10209(13) 0.21888(12) 0.0326(3) Uani 1 1 d . . . H1 H 0.2422 0.2190 0.1597 0.042 Uiso 1 1 calc R . . C2 C 0.21510(11) -0.05220(14) 0.08134(14) 0.0402(3) Uani 1 1 d . . . H2 H 0.1580 -0.0152 -0.0252 0.052 Uiso 1 1 calc R . . C3 C 0.33844(14) -0.07217(19) 0.0504(2) 0.0586(4) Uani 1 1 d . . . H3A H 0.3478 -0.1918 -0.0003 0.076 Uiso 1 1 calc R . . H3B H 0.3536 0.0240 -0.0271 0.076 Uiso 1 1 calc R . . C4 C 0.42132(12) -0.0536(2) 0.2300(2) 0.0612(4) Uani 1 1 d . . . H4A H 0.4928 0.0103 0.2221 0.080 Uiso 1 1 calc R . . H4B H 0.4422 -0.1746 0.2811 0.080 Uiso 1 1 calc R . . C5 C 0.35446(10) 0.05796(15) 0.34001(17) 0.0433(3) Uani 1 1 d . . . H5A H 0.3448 -0.0138 0.4394 0.056 Uiso 1 1 calc R . . H5B H 0.3964 0.1711 0.3818 0.056 Uiso 1 1 calc R . . C6 C 0.13312(8) 0.12307(12) 0.30682(12) 0.0299(3) Uani 1 1 d . . . O1 O 0.17852(8) -0.21545(11) 0.15460(11) 0.0435(3) Uani 1 1 d . . . H1A H 0.1785 -0.3029 0.0884 0.057 Uiso 1 1 calc R . . O2 O 0.12981(7) 0.03954(10) 0.44220(10) 0.0384(3) Uani 1 1 d . . . N3 N 0.04795(8) 0.23645(14) 0.22708(12) 0.0415(3) Uani 1 1 d . . . H3C H -0.0125 0.2541 0.2694 0.054 Uiso 1 1 calc R . . H3D H 0.0532 0.2922 0.1331 0.054 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 C1 0.0378(5) 0.0265(5) 0.0378(6) 0.0016(3) 0.0173(4) 0.0009(4) C2 0.0521(7) 0.0376(6) 0.0352(5) -0.0025(4) 0.0189(5) -0.0010(4) C3 0.0745(9) 0.0452(7) 0.0739(9) -0.0085(6) 0.0528(8) -0.0031(6) C4 0.0445(7) 0.0541(8) 0.0946(11) -0.0074(7) 0.0358(7) 0.0043(5) C5 0.0345(6) 0.0383(6) 0.0586(7) -0.0053(5) 0.0140(5) -0.0010(4) C6 0.0336(5) 0.0264(5) 0.0312(5) -0.0039(3) 0.0109(4) -0.0018(3) O1 0.0519(5) 0.0357(5) 0.0478(5) -0.0110(3) 0.0215(4) -0.0104(3) O2 0.0471(5) 0.0359(5) 0.0371(5) 0.0038(3) 0.0196(3) 0.0025(3) N3 0.0396(5) 0.0452(6) 0.0422(5) 0.0054(4) 0.0147(4) 0.0102(4) _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 C6 1.5163(13) . ? C1 C5 1.5334(16) . ? C1 C2 1.5358(14) . ? C2 O1 1.4236(13) . ? C2 C3 1.5257(18) . ? C3 C4 1.523(3) . ? C4 C5 1.5294(18) . ? C6 O2 1.2368(12) . ? C6 N3 1.3277(14) . ? 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 C6 C1 C5 115.70(9) . . ? C6 C1 C2 113.38(8) . . ? C5 C1 C2 104.50(9) . . ? O1 C2 C3 111.92(10) . . ? O1 C2 C1 108.76(8) . . ? C3 C2 C1 101.29(10) . . ? C4 C3 C2 105.03(11) . . ? C3 C4 C5 106.15(11) . . ? C1 C5 C4 105.68(11) . . ? O2 C6 N3 122.55(9) . . ? O2 C6 C1 122.37(9) . . ? N3 C6 C1 115.07(9) . . ? 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 C6 C1 C2 O1 -48.69(12) . . . . ? C5 C1 C2 O1 78.17(11) . . . . ? C6 C1 C2 C3 -166.72(9) . . . . ? C5 C1 C2 C3 -39.86(11) . . . . ? O1 C2 C3 C4 -76.02(12) . . . . ? C1 C2 C3 C4 39.70(12) . . . . ? C2 C3 C4 C5 -24.67(14) . . . . ? C6 C1 C5 C4 150.64(9) . . . . ? C2 C1 C5 C4 25.24(12) . . . . ? C3 C4 C5 C1 -0.49(14) . . . . ? C5 C1 C6 O2 -29.54(13) . . . . ? C2 C1 C6 O2 91.18(12) . . . . ? C5 C1 C6 N3 150.96(9) . . . . ? C2 C1 C6 N3 -88.32(11) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1A O2 0.82 2.07 2.8586(11) 162.2 4 N3 H3C O1 0.86 2.17 3.0299(14) 172.7 2 N3 H3D O2 0.86 2.28 3.1023(13) 160.3 4_565 _diffrn_measured_fraction_theta_max 0.957 _diffrn_reflns_theta_full 74.91 _diffrn_measured_fraction_theta_full 0.957 _refine_diff_density_max 0.308 _refine_diff_density_min -0.172 _refine_diff_density_rms 0.048 # end of c(bg1cn) # ============================================================