#------------------------------------------------------------------------------
#$Date: 2011-09-10 05:16:28 +0200 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2009096.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, M.'
'Jones, P. 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_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)
_[local]_cod_data_source_file    bm1355.cif
_[local]_cod_data_source_block   primo
_[local]_cod_cif_authors_sg_H-M  'P 21/n'
_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_database_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_type_symbol
I 0.667721(15) 0.017017(10) 0.263222(14) 0.02190(6) Uani d . 1 I
N 0.2496(2) 0.13039(13) 0.1412(2) 0.0238(3) Uani d . 1 N
H1' 0.345(3) 0.0935(19) 0.169(3) 0.025(6) Uiso d . 1 H
H2' 0.185(4) 0.093(2) 0.068(3) 0.042(7) Uiso d . 1 H
O 0.40215(18) 0.40194(10) 0.44136(17) 0.0217(3) Uani d . 1 O
H3' 0.354(3) 0.4108(19) 0.514(3) 0.029(7) Uiso d . 1 H
C1 0.1603(3) 0.14806(17) 0.2945(2) 0.0283(4) Uani d . 1 C
H1A 0.1461 0.0782 0.3513 0.034 Uiso calc R 1 H
H1B 0.0439 0.1789 0.2601 0.034 Uiso calc R 1 H
C2 0.2658(3) 0.22443(15) 0.4160(2) 0.0222(4) Uani d . 1 C
H2A 0.3781 0.1904 0.4580 0.027 Uiso calc R 1 H
H2B 0.2034 0.2383 0.5142 0.027 Uiso calc R 1 H
C3 0.2976(2) 0.33061(14) 0.3299(2) 0.0172(3) Uani d . 1 C
H3 0.1842 0.3660 0.2905 0.021 Uiso calc R 1 H
C4 0.3932(2) 0.30883(14) 0.1788(2) 0.0196(4) Uani d . 1 C
H4A 0.4128 0.3777 0.1213 0.023 Uiso calc R 1 H
H4B 0.5074 0.2763 0.2180 0.023 Uiso calc R 1 H
C5 0.2890(3) 0.23283(15) 0.0550(2) 0.0237(4) Uani d . 1 C
H5A 0.1795 0.2682 0.0076 0.028 Uiso calc R 1 H
H5B 0.3554 0.2164 -0.0395 0.028 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 0.02013(8) 0.02256(9) 0.02322(8) 0.00091(5) 0.00359(5) 0.00099(4)
N 0.0212(9) 0.0195(8) 0.0297(8) -0.0018(7) -0.0002(7) -0.0065(6)
O 0.0229(7) 0.0199(6) 0.0222(6) -0.0025(5) 0.0029(6) -0.0062(5)
C1 0.0245(10) 0.0278(10) 0.0337(10) -0.0091(8) 0.0077(9) -0.0039(8)
C2 0.0220(10) 0.0240(9) 0.0215(8) -0.0057(8) 0.0058(7) 0.0001(6)
C3 0.0137(8) 0.0170(8) 0.0201(8) 0.0013(7) 0.0000(7) -0.0021(6)
C4 0.0211(9) 0.0181(8) 0.0196(8) -0.0033(7) 0.0025(7) -0.0003(6)
C5 0.0257(10) 0.0239(9) 0.0205(8) -0.0004(8) -0.0006(8) -0.0025(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_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