#------------------------------------------------------------------------------ #$Date: 2012-02-03 19:16:24 +0200 (Fri, 03 Feb 2012) $ #$Revision: 32112 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/20/00/2200018.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2200018 loop_ _publ_author_name 'Stapleton, Clynton P. D.' 'Tiekink, Edward R. T.' _publ_section_title ; DL-Piperidine-2-carboxylic acid ; _journal_issue 1 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o75 _journal_page_last o76 _journal_volume 57 _journal_year 2001 _chemical_formula_sum 'C6 H11 N O2' _chemical_formula_weight 129.16 _chemical_name_common 'dl-homoproline, dl-pipecolic acid' _chemical_name_systematic ; ? ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _cell_angle_alpha 90 _cell_angle_beta 110.39(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 11.148(3) _cell_length_b 5.822(2) _cell_length_c 10.813(4) _cell_measurement_reflns_used 14 _cell_measurement_temperature 173.0(10) _cell_measurement_theta_max 12.1 _cell_measurement_theta_min 7.4 _cell_volume 657.8(4) _computing_cell_refinement 'MSC/AFC Diffractometer Control Software' _computing_data_collection ; MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1996) ; _computing_data_reduction 'TEXSAN (Molecular Structure Corporation, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material TEXSAN _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _diffrn_ambient_temperature 173.0(10) _diffrn_measured_fraction_theta_full .999 _diffrn_measured_fraction_theta_max .999 _diffrn_measurement_device_type 'Rigaku AFC-7R' _diffrn_measurement_method \w-2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'rotating anode' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71069 _diffrn_reflns_av_R_equivalents .018 _diffrn_reflns_av_sigmaI/netI .029 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 3323 _diffrn_reflns_theta_full 27.51 _diffrn_reflns_theta_max 27.5 _diffrn_reflns_theta_min 3.8 _diffrn_standards_decay_% .7 _diffrn_standards_interval_count 400 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu .10 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.304 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 280 _exptl_crystal_size_max .30 _exptl_crystal_size_mid .20 _exptl_crystal_size_min .10 _refine_diff_density_max .24 _refine_diff_density_min -.19 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref .98 _refine_ls_hydrogen_treatment noref _refine_ls_matrix_type full _refine_ls_number_parameters 83 _refine_ls_number_reflns 1513 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all .98 _refine_ls_R_factor_all .050 _refine_ls_R_factor_gt .035 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean <0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.1000P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .128 _reflns_number_gt 1191 _reflns_number_total 1513 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file cf6001.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/c' _cod_database_code 2200018 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' 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 O21 .09484(8) .37073(16) .30718(9) .0275(3) Uani d . 1 . . O O22 .18325(10) .20556(18) .50530(9) .0359(3) Uani d . 1 . . O N1 .13411(9) -.00698(16) .17974(9) .0175(3) Uani d . 1 . . N H1 .1467 .1219 .1366 .0342(13) Uiso d . 1 . . H H2 .0481 -.0174 .1663 .0342(13) Uiso d . 1 . . H C2 .20693(11) .01657(19) .32359(10) .0180(3) Uani d . 1 . . C H3 .1955 -.1282 .3680 .0342(13) Uiso d . 1 . . H C3 .34878(11) .0429(2) .34526(12) .0253(3) Uani d . 1 . . C H4 .3978 .0585 .4407 .0342(13) Uiso d . 1 . . H H5 .3624 .1835 .3004 .0342(13) Uiso d . 1 . . H C4 .39645(11) -.1668(3) .29050(13) .0315(3) Uani d . 1 . . C H6 .4874 -.1445 .3004 .0342(13) Uiso d . 1 . . H H7 .3905 -.3051 .3413 .0342(13) Uiso d . 1 . . H C5 .31718(12) -.2021(2) .14553(13) .0283(3) Uani d . 1 . . C H8 .3442 -.3461 .1141 .0342(13) Uiso d . 1 . . H H9 .3331 -.0735 .0933 .0342(13) Uiso d . 1 . . H C6 .17490(11) -.2146(2) .12337(11) .0227(3) Uani d . 1 . . C H10 .1256 -.2242 .0276 .0342(13) Uiso d . 1 . . H H11 .1568 -.3544 .1660 .0342(13) Uiso d . 1 . . H C21 .15627(11) .2162(2) .38344(11) .0204(3) Uani d . 1 . . C 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 O21 .0283(4) .0240(5) .0351(5) .0079(4) .0170(4) .0049(4) O22 .0577(7) .0307(6) .0238(5) .0092(4) .0196(4) -.0037(4) N1 .0182(5) .0180(5) .0171(5) -.0004(3) .0069(4) .0001(3) C2 .0199(5) .0196(6) .0156(5) .0022(4) .0075(4) .0004(4) C3 .0181(6) .0320(7) .0251(6) .0014(5) .0067(4) -.0073(5) C4 .0222(6) .0398(8) .0320(7) .0099(5) .0088(5) -.0073(6) C5 .0279(6) .0325(7) .0287(7) .0041(5) .0151(5) -.0059(5) C6 .0262(6) .0214(6) .0218(6) .0001(5) .0100(5) -.0045(4) C21 .0217(5) .0178(6) .0254(6) -.0009(4) .0128(4) -.0021(4) 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 O21 C21 . 1.2508(15) ? O22 C21 . 1.2468(15) ? N1 C2 . 1.4891(15) ? N1 C6 . 1.4943(15) ? C2 C3 . 1.5234(16) ? C2 C21 . 1.5309(15) ? C3 C4 . 1.5305(18) ? C4 C5 . 1.5216(18) ? C5 C6 . 1.5210(16) ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C2 N1 C6 111.59(9) N1 C2 C3 109.20(9) N1 C2 C21 111.37(9) C3 C2 C21 112.00(10) C2 C3 C4 110.00(10) C5 C4 C3 110.54(10) C6 C5 C4 111.61(10) N1 C6 C5 110.22(9) O22 C21 O21 127.42(11) O22 C21 C2 114.85(10) O21 C21 C2 117.72(10) loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag N1 H1 O22 4_565 0.92 1.90 2.7672(17) 157 yes N1 H2 O21 2_545 0.92 1.83 2.7005(17) 156 yes