#------------------------------------------------------------------------------ #$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301791 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/90/2009096.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_2009096 loop_ _publ_author_name 'Freytag, Matthias' 'Jones, Peter G.' _publ_section_title ; Hydrogen bonding in two piperidinium derivatives ; _journal_issue 11 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1874 _journal_page_last 1877 _journal_paper_doi 10.1107/S0108270199009567 _journal_volume 55 _journal_year 1999 _chemical_formula_moiety 'C5 H12 N O 1+, I 1-' _chemical_formula_sum 'C5 H12 I N O' _chemical_formula_weight 229.06 _chemical_name_systematic ; 4-Hydroxypiperidinium iodide ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 97.480(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 7.7939(8) _cell_length_b 12.3957(14) _cell_length_c 7.9780(10) _cell_measurement_reflns_used 62 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 12.5 _cell_measurement_theta_min 3.0 _cell_volume 764.20(15) _computing_cell_refinement XSCANS _computing_data_collection 'XSCANS (Fait, 1991)' _computing_data_reduction XSCANS _computing_molecular_graphics 'XP (Siemens, 1994b)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997a)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997b)' _diffrn_ambient_temperature 173(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Siemens P4' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.023 _diffrn_reflns_av_sigmaI/netI 0.0173 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_number 5555 _diffrn_reflns_theta_full 27.50 _diffrn_reflns_theta_max 27.5 _diffrn_reflns_theta_min 3.05 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 247 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 4.107 _exptl_absorpt_correction_T_max 0.996 _exptl_absorpt_correction_T_min 0.702 _exptl_absorpt_correction_type '\y scan' _exptl_absorpt_process_details '(XEMP; Siemens, 1994a)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.991 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 440 _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _refine_diff_density_max 0.50 _refine_diff_density_min -0.47 _refine_ls_extinction_coef 0.0357(8) _refine_ls_extinction_method 'SHELXL97 (Sheldrick, 1997a)' _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 86 _refine_ls_number_reflns 1750 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.071 _refine_ls_R_factor_all 0.017 _refine_ls_R_factor_gt 0.014 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0193P)^2^+0.1398P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref 0.035 _reflns_number_gt 1595 _reflns_number_total 1750 _reflns_threshold_expression I>2\sa(I) _cod_data_source_file bm1355.cif _cod_data_source_block primo _cod_depositor_comments ; The following automatic conversions were performed: '_geom_torsion_publ_flag' value 'Y' changed to 'y' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (8 times). Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 2009096 _cod_database_fobs_code 2009096 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -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 I .667721(15) .017017(10) .263222(14) .02190(6) Uani d . 1 . . I N .2496(2) .13039(13) .1412(2) .0238(3) Uani d . 1 . . N H1' .345(3) .0935(19) .169(3) .025(6) Uiso d . 1 . . H H2' .185(4) .093(2) .068(3) .042(7) Uiso d . 1 . . H O .40215(18) .40194(10) .44136(17) .0217(3) Uani d . 1 . . O H3' .354(3) .4108(19) .514(3) .029(7) Uiso d . 1 . . H C1 .1603(3) .14806(17) .2945(2) .0283(4) Uani d . 1 . . C H1A .1461 .0782 .3513 .034 Uiso calc R 1 . . H H1B .0439 .1789 .2601 .034 Uiso calc R 1 . . H C2 .2658(3) .22443(15) .4160(2) .0222(4) Uani d . 1 . . C H2A .3781 .1904 .4580 .027 Uiso calc R 1 . . H H2B .2034 .2383 .5142 .027 Uiso calc R 1 . . H C3 .2976(2) .33061(14) .3299(2) .0172(3) Uani d . 1 . . C H3 .1842 .3660 .2905 .021 Uiso calc R 1 . . H C4 .3932(2) .30883(14) .1788(2) .0196(4) Uani d . 1 . . C H4A .4128 .3777 .1213 .023 Uiso calc R 1 . . H H4B .5074 .2763 .2180 .023 Uiso calc R 1 . . H C5 .2890(3) .23283(15) .0550(2) .0237(4) Uani d . 1 . . C H5A .1795 .2682 .0076 .028 Uiso calc R 1 . . H H5B .3554 .2164 -.0395 .028 Uiso calc R 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 I .02013(8) .02256(9) .02322(8) .00091(5) .00359(5) .00099(4) N .0212(9) .0195(8) .0297(8) -.0018(7) -.0002(7) -.0065(6) O .0229(7) .0199(6) .0222(6) -.0025(5) .0029(6) -.0062(5) C1 .0245(10) .0278(10) .0337(10) -.0091(8) .0077(9) -.0039(8) C2 .0220(10) .0240(9) .0215(8) -.0057(8) .0058(7) .0001(6) C3 .0137(8) .0170(8) .0201(8) .0013(7) .0000(7) -.0021(6) C4 .0211(9) .0181(8) .0196(8) -.0033(7) .0025(7) -.0003(6) C5 .0257(10) .0239(9) .0205(8) -.0004(8) -.0006(8) -.0025(7) 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 '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 C5 N C1 113.32(15) y N C1 C2 109.94(16) ? C1 C2 C3 110.99(15) ? O C3 C2 111.55(14) ? O C3 C4 107.70(14) ? C2 C3 C4 109.26(14) ? C5 C4 C3 110.44(15) ? N C5 C4 110.60(14) ? 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 N C5 . 1.495(2) y N C1 . 1.500(2) y O C3 . 1.431(2) y C1 C2 . 1.518(3) ? C2 C3 . 1.520(2) ? C3 C4 . 1.521(2) ? C4 C5 . 1.521(2) ? 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 N H1' I . 0.88(2) 2.70(3) 3.566(2) 169(2) y N H2' O 4_565 0.85(3) 2.30(3) 2.985(2) 137(2) y N H2' O 2_545 0.85(3) 2.46(3) 3.106(2) 133(2) y N H2' I 3_655 0.85(3) 3.31(3) 3.835(2) 122(2) y O H3' I 4_566 0.74(2) 2.76(3) 3.4880(10) 169(2) y C3 H3 I 2 1.00 3.30 4.283(2) 167 y C5 H5A I 4_565 0.99 3.29 3.919(2) 123 y C5 H5B I 3_655 0.99 3.39 4.047(2) 125 y 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_publ_flag C5 N C1 C2 -54.8(2) y N C1 C2 C3 56.5(2) y C1 C2 C3 O -177.95(15) y C1 C2 C3 C4 -59.0(2) y O C3 C4 C5 179.78(14) y C2 C3 C4 C5 58.45(19) y C1 N C5 C4 54.9(2) y C3 C4 C5 N -56.2(2) y loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21136106 2 PubChem 139056877