#------------------------------------------------------------------------------
#$Date: 2016-02-20 17:35:30 +0100 (Sat 20 de Feb de 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/75/2217592.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_2217592
loop_
_publ_author_name
'Li Zhang'
'Peng-Wei Zhang'
'Xiao-Hui Wang'
'Li Chen'
'Qu-Fei Shen'
_publ_section_title
;
 4-Hydroxy-2,2,6,6-tetramethylpiperidinium chloride--hydroxonium
 chloride (3/1)
;
_journal_coeditor_code           NC2088
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o512
_journal_page_last               o512
_journal_paper_doi               10.1107/S1600536808002158
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C9 H20 N O +, Cl-, 0.33(H3 O +, Cl -)'
_chemical_formula_moiety         'C9 H20 N O +, 0.33(H3 O +), 1.33(Cl -)'
_chemical_formula_sum            'C9 H21 Cl1.33 N O1.33'
_chemical_formula_weight         211.87
_chemical_name_systematic
;4-Hydroxy-2,2,6,6-tetramethylpiperidinium chloride--hydroxonium chloride
 (3/1)
;
_space_group_IT_number           176
_symmetry_cell_setting           hexagonal
_symmetry_space_group_name_Hall  '-P 6c'
_symmetry_space_group_name_H-M   'P 63/m'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            6
_cell_length_a                   13.4460(19)
_cell_length_b                   13.4460(19)
_cell_length_c                   11.528(2)
_cell_measurement_reflns_used    4368
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.920
_cell_measurement_theta_min      1.749
_cell_volume                     1805.0(5)
_computing_cell_refinement       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_collection       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0753
_diffrn_reflns_av_sigmaI/netI    0.0371
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14051
_diffrn_reflns_theta_full        27.90
_diffrn_reflns_theta_max         27.90
_diffrn_reflns_theta_min         2.49
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.360
_exptl_absorpt_correction_T_max  0.9891
_exptl_absorpt_correction_T_min  0.9678
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku/MSC, 2005)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.170
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             692
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.255
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     68
_refine_ls_number_reflns         1513
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0505
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0699P)²+0.5807P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1257
_refine_ls_wR_factor_ref         0.1297
_reflns_number_gt                1424
_reflns_number_total             1513
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            nc2088.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Hexagonal' changed to 'hexagonal'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Hexagonal' changed to 'hexagonal'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1804.9(5)
_cod_database_code               2217592
_cod_database_fobs_code          2217592
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'-x, -y, z+1/2'
'y, -x+y, z+1/2'
'x-y, x, z+1/2'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'x, y, -z-1/2'
'-y, x-y, -z-1/2'
'-x+y, -x, -z-1/2'
loop_
_atom_site_type_symbol
_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
O O1 -0.13431(15) 0.43006(16) 0.2500 0.0420(6) Uani d S 1
H H1 -0.0986 0.5031 0.2500 0.050 Uiso d SR 1
N N1 0.16134(16) 0.39830(16) 0.2500 0.0174(4) Uani d S 1
H H1B 0.2019 0.3598 0.2500 0.021 Uiso calc SR 1
H H1C 0.2145 0.4755 0.2500 0.021 Uiso calc SR 1
C C1 -0.0587(2) 0.3833(2) 0.2500 0.0283(6) Uani d S 1
H H1A -0.1063 0.2976 0.2500 0.034 Uiso calc SR 1
C C2 0.01605(15) 0.42088(15) 0.35766(18) 0.0260(4) Uani d . 1
H H2A -0.0339 0.3965 0.4271 0.031 Uiso calc R 1
H H2B 0.0625 0.5058 0.3587 0.031 Uiso calc R 1
C C3 0.09668(15) 0.37155(15) 0.36468(16) 0.0213(4) Uani d . 1
C C4 0.03335(16) 0.24188(16) 0.38919(18) 0.0279(4) Uani d . 1
H H4A -0.0362 0.2037 0.3415 0.042 Uiso calc R 1
H H4B 0.0123 0.2284 0.4714 0.042 Uiso calc R 1
H H4C 0.0836 0.2108 0.3702 0.042 Uiso calc R 1
C C5 0.18849(18) 0.43315(17) 0.45708(17) 0.0302(4) Uani d . 1
H H5A 0.2438 0.4060 0.4542 0.045 Uiso calc R 1
H H5B 0.1523 0.4170 0.5338 0.045 Uiso calc R 1
H H5C 0.2283 0.5161 0.4426 0.045 Uiso calc R 1
Cl Cl1 0.6667 0.3333 0.7500 0.0219(3) Uani d S 1
Cl Cl2 0.71701(5) 0.03169(5) 0.2500 0.0244(2) Uani d S 1
O O2 0.6667 0.3333 0.3252(4) 0.0276(10) Uani d SP 0.50
H H2 0.7352 0.3704 0.2999 0.041 Uiso d PR 0.50
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
O1 0.0168(9) 0.0200(9) 0.091(2) 0.0103(8) 0.000 0.000
N1 0.0169(9) 0.0186(9) 0.0159(11) 0.0083(8) 0.000 0.000
C1 0.0176(12) 0.0170(11) 0.052(2) 0.0096(9) 0.000 0.000
C2 0.0239(9) 0.0212(8) 0.0318(11) 0.0105(7) 0.0114(8) 0.0049(7)
C3 0.0232(8) 0.0232(8) 0.0173(9) 0.0114(7) 0.0050(7) 0.0036(6)
C4 0.0278(9) 0.0248(9) 0.0313(11) 0.0133(8) 0.0075(8) 0.0092(8)
C5 0.0376(10) 0.0329(10) 0.0162(10) 0.0146(9) -0.0007(8) 0.0022(8)
Cl1 0.0202(3) 0.0202(3) 0.0254(6) 0.01012(16) 0.000 0.000
Cl2 0.0251(3) 0.0203(3) 0.0295(4) 0.0125(2) 0.000 0.000
O2 0.0243(14) 0.0243(14) 0.034(3) 0.0121(7) 0.000 0.000
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'
Cl Cl 0.1484 0.1585 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C1 O1 H1 . . 113.0
C3 N1 C3 . 10_556 120.43(18)
C3 N1 H1B . . 107.2
C3 N1 H1B 10_556 . 107.2
C3 N1 H1C . . 107.2
C3 N1 H1C 10_556 . 107.2
H1B N1 H1C . . 106.9
O1 C1 C2 . . 110.50(13)
O1 C1 C2 . 10_556 110.51(13)
C2 C1 C2 . 10_556 109.9(2)
O1 C1 H1A . . 108.6
C2 C1 H1A . . 108.6
C2 C1 H1A 10_556 . 108.6
C1 C2 C3 . . 113.23(16)
C1 C2 H2A . . 108.9
C3 C2 H2A . . 108.9
C1 C2 H2B . . 108.9
C3 C2 H2B . . 108.9
H2A C2 H2B . . 107.7
N1 C3 C5 . . 105.47(14)
N1 C3 C2 . . 107.23(15)
C5 C3 C2 . . 111.00(16)
N1 C3 C4 . . 110.77(15)
C5 C3 C4 . . 109.09(15)
C2 C3 C4 . . 113.01(14)
C3 C4 H4A . . 109.5
C3 C4 H4B . . 109.5
H4A C4 H4B . . 109.5
C3 C4 H4C . . 109.5
H4A C4 H4C . . 109.5
H4B C4 H4C . . 109.5
C3 C5 H5A . . 109.5
C3 C5 H5B . . 109.5
H5A C5 H5B . . 109.5
C3 C5 H5C . . 109.5
H5A C5 H5C . . 109.5
H5B C5 H5C . . 109.5
O2 O2 H2 10_556 . 69.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O1 C1 . 1.438(3)
O1 H1 . 0.8500
N1 C3 . 1.523(2)
N1 C3 10_556 1.523(2)
N1 H1B . 0.9200
N1 H1C . 0.9200
C1 C2 . 1.516(2)
C1 C2 10_556 1.516(2)
C1 H1A . 1.0000
C2 C3 . 1.530(2)
C2 H2A . 0.9900
C2 H2B . 0.9900
C3 C5 . 1.524(3)
C3 C4 . 1.536(2)
C4 H4A . 0.9800
C4 H4B . 0.9800
C4 H4C . 0.9800
C5 H5A . 0.9800
C5 H5B . 0.9800
C5 H5C . 0.9800
O2 O2 10_556 1.733(10)
O2 H2 . 0.8501
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
O1 H1 Cl2 2 0.85 2.15 2.991(2) 172.0
N1 H1B Cl2 3_665 0.92 2.22 3.139(2) 174.6
N1 H1C Cl1 7_666 0.92 2.25 3.166(2) 175.7
O2 H2 O1 1_655 0.85 1.63 2.475(2) 174.8
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_site_symmetry_1
_geom_torsion
O1 C1 C2 C3 . 178.55(15)
C2 C1 C2 C3 10_556 -59.2(2)
C3 N1 C3 C5 10_556 -167.57(14)
C3 N1 C3 C2 10_556 -49.2(2)
C3 N1 C3 C4 10_556 74.5(2)
C1 C2 C3 N1 . 51.7(2)
C1 C2 C3 C5 . 166.46(16)
C1 C2 C3 C4 . -70.6(2)
