#------------------------------------------------------------------------------ #$Date: 2025-08-19 07:12:48 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301798 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/21/2012112.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_2012112 loop_ _publ_author_name 'Delgado, Gerzon' 'Mora, Asilo\'e J.' 'Bahsas, Ali' _publ_section_title ; Zwitterionic 4-piperidinecarboxylic acid monohydrate ; _journal_issue 8 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 965 _journal_page_last 967 _journal_paper_doi 10.1107/S0108270101007958 _journal_volume 57 _journal_year 2001 _chemical_formula_moiety 'C6 H11 N O2 , H2 O' _chemical_formula_sum 'C6 H13 N O3' _chemical_formula_weight 147.17 _chemical_name_common 'isonipecotic acid' _chemical_name_systematic ; 4-piperidinecarboxylic acid ; _space_group_IT_number 33 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2c -2n' _symmetry_space_group_name_H-M 'P n a 21' _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 11.9647(11) _cell_length_b 8.3276(7) _cell_length_c 7.6054(7) _cell_measurement_reflns_used 4773 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 25.4 _cell_measurement_theta_min 1.5 _cell_volume 757.78(12) _computing_cell_refinement 'SAINT (Siemens, 1996)' _computing_data_collection 'SMART (Siemens, 1996)' _computing_data_reduction 'SHELXTL (Siemens, 1996)' _computing_molecular_graphics 'ORTEPIII (Burnett & Johnson, 1996; Farrugia, 1997)' _computing_publication_material 'PLATON (Spek, 2000)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Siemens CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .038 _diffrn_reflns_av_sigmaI/netI .0140 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_number 6524 _diffrn_reflns_theta_full 25.36 _diffrn_reflns_theta_max 25.36 _diffrn_reflns_theta_min 2.98 _exptl_absorpt_coefficient_mu .103 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.290 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 320 _exptl_crystal_size_max .4 _exptl_crystal_size_mid .4 _exptl_crystal_size_min .3 _refine_diff_density_max .292 _refine_diff_density_min -.192 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.05 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 105 _refine_ls_number_reflns 754 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.05 _refine_ls_R_factor_all .038 _refine_ls_R_factor_gt .037 _refine_ls_shift/su_max .012 _refine_ls_shift/su_mean .001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0654P)^2^+0.1836P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .101 _reflns_number_gt 734 _reflns_number_total 754 _reflns_threshold_expression I>2\s(I) _cod_data_source_file bk1590.cif _cod_data_source_block I _cod_database_code 2012112 _cod_database_fobs_code 2012112 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, 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 C1 .1857(2) .0763(3) .3030(3) .0319(5) Uani d . 1 . . C C2 .1668(2) .0637(3) .1041(3) .0303(5) Uani d . 1 . . C H2 .1411 -.0456 .0790 .036 Uiso calc . 1 . . H C3 .0790(2) .1790(3) .0341(3) .0380(6) Uani d . 1 . . C H3A .1000 .2882 .0635 .046 Uiso calc . 1 . . H H3B .0077 .1564 .0898 .046 Uiso calc . 1 . . H C4 .0669(2) .1634(3) -.1647(4) .0453(7) Uani d . 1 . . C H4A .0385 .0575 -.1935 .054 Uiso calc . 1 . . H H4B .0136 .2423 -.2070 .054 Uiso calc . 1 . . H C5 .2622(3) .0720(4) -.1905(4) .0453(7) Uani d . 1 . . C H5A .3327 .0929 -.2494 .054 Uiso calc . 1 . . H H5B .2391 -.0366 -.2188 .054 Uiso calc . 1 . . H C6 .2772(2) .0885(3) .0064(4) .0404(6) Uani d . 1 . . C H6A .3063 .1945 .0330 .048 Uiso calc . 1 . . H H6B .3313 .0099 .0467 .048 Uiso calc . 1 . . H N1 .1760(2) .1883(3) -.2530(3) .0393(5) Uani d . 1 . . N H1A .200(3) .285(4) -.220(5) .048(8) Uiso d . 1 . . H H1B .166(3) .172(3) -.374(5) .047(9) Uiso d . 1 . . H O1 .2552(2) -.0179(2) .3692(3) .0476(5) Uani d . 1 . . O O2 .1331(2) .1781(3) .3884(3) .0544(6) Uani d . 1 . . O OW1 .4490(3) .1485(6) -.5067(5) .120(2) Uani d . 1 . . O H1W .497(6) .192(8) -.580(10) .144 Uiso d . 1 . . H H2W .405(5) .090(7) -.570(10) .144 Uiso d . 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 C1 .0399(8) .0366(9) .0199(8) -.0016(6) .0001(7) .0023(6) C2 .0388(9) .0315(8) .0206(9) -.0025(6) -.0001(6) .0014(6) C3 .0365(9) .0520(10) .0260(10) .0030(7) -.0006(7) .0054(8) C4 .0460(10) .0610(10) .0290(10) -.0047(8) -.0108(8) .0074(8) C5 .0570(10) .0540(10) .0265(9) .0048(9) .0112(8) .0017(9) C6 .0403(9) .0550(10) .0264(9) .0041(7) .0016(8) .0050(8) N1 .0610(10) .0400(8) .0182(7) -.0066(7) -.0008(7) .0016(6) O1 .0660(8) .0462(8) .0302(7) .0141(6) -.0118(6) .0007(6) O2 .0696(9) .0689(9) .0251(6) .0289(8) -.0033(6) -.0068(6) OW1 .100(2) .192(3) .0640(10) -.084(2) .0140(10) -.026(2) 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' O O .0106 .0060 '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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag O2 C1 O1 123.8(2) yes O2 C1 C2 119.2(2) yes O1 C1 C2 116.9(2) yes C3 C2 C6 110.0(2) ? C3 C2 C1 113.8(2) ? C6 C2 C1 110.0(2) ? C2 C3 C4 111.0(2) ? N1 C4 C3 110.7(2) yes N1 C5 C6 109.8(2) yes C5 C6 C2 111.5(2) ? C4 N1 C5 111.9(2) yes 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 C1 O2 . 1.240(3) yes C1 O1 . 1.248(3) yes C1 C2 . 1.534(3) yes C2 C3 . 1.519(3) yes C2 C6 . 1.530(3) yes C3 C4 . 1.525(3) yes C4 N1 . 1.483(4) yes C5 N1 . 1.493(4) yes C5 C6 . 1.514(4) yes 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 N1 H1A O1 4_554 .89(4) 1.86(4) 2.744(3) 175(4) N1 H1B O2 1_554 .94(4) 1.85(4) 2.776(3) 169(3) OW1 H1W O2 3_554 .87(8) 1.97(7) 2.752(4) 149(8) OW1 H2W O1 1_554 .85(7) 2.06(6) 2.862(4) 157(7) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21107365 2 PubChem 139058276