#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/14/2231476.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_2231476
loop_
_publ_author_name
'Betz, Richard'
'Gerber, Thomas'
'Hosten, Eric'
_publ_section_title
;
 3-Hydroxy-2-(hydroxymethyl)pyridinium chloride
;
_journal_coeditor_code           FY2019
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2348
_journal_paper_doi               10.1107/S1600536811032405
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C6 H8 N O2 +, Cl -'
_chemical_formula_moiety         'C6 H8 N O2 +, Cl -'
_chemical_formula_sum            'C6 H8 Cl N O2'
_chemical_formula_weight         161.58
_chemical_name_systematic
;
3-Hydroxy-2-(hydroxymethyl)pyridinium chloride
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                73.8950(10)
_cell_angle_beta                 68.6340(10)
_cell_angle_gamma                86.8010(10)
_cell_formula_units_Z            2
_cell_length_a                   6.8490(2)
_cell_length_b                   7.1376(2)
_cell_length_c                   7.9675(2)
_cell_measurement_reflns_used    4561
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.24
_cell_measurement_theta_min      2.86
_cell_volume                     348.044(17)
_computing_cell_refinement       'SAINT (Bruker, 2010)'
_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_data_reduction        'SAINT (Bruker, 2010)'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2008)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω'
_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  0.0187
_diffrn_reflns_av_sigmaI/netI    0.0156
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            6143
_diffrn_reflns_theta_full        28.31
_diffrn_reflns_theta_max         28.31
_diffrn_reflns_theta_min         2.86
_exptl_absorpt_coefficient_mu    0.481
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8343
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.542
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             168
_exptl_crystal_size_max          0.242
_exptl_crystal_size_mid          0.174
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.174
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     103
_refine_ls_number_reflns         1711
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0280
_refine_ls_R_factor_gt           0.0252
_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/[σ²(Fo²)+(0.0395P)²+0.0944P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0709
_refine_ls_wR_factor_ref         0.0730
_reflns_number_gt                1572
_reflns_number_total             1711
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fy2019.cif
_cod_data_source_block           I
_cod_database_code               2231476
_cod_database_fobs_code          2231476
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
_atom_site_symmetry_multiplicity
O O1 0.25186(15) 0.42693(12) 0.51787(12) 0.0286(2) Uani d . 1 1
H H81 0.240(3) 0.382(3) 0.624(3) 0.047(5) Uiso d . 1 1
O O2 0.29516(16) 0.75828(14) -0.01815(11) 0.0325(2) Uani d . 1 1
H H82 0.166(3) 0.776(3) 0.001(3) 0.051(5) Uiso d . 1 1
N N1 0.27167(14) 0.91926(14) 0.25202(13) 0.0221(2) Uani d . 1 1
H H71 0.276(2) 0.980(2) 0.142(2) 0.035(4) Uiso d . 1 1
C C1 0.26774(16) 0.72440(15) 0.29807(14) 0.0197(2) Uani d . 1 1
C C2 0.25517(16) 0.62326(15) 0.47898(15) 0.0205(2) Uani d . 1 1
C C3 0.24780(18) 0.72716(16) 0.60447(15) 0.0243(2) Uani d . 1 1
H H3 0.2386 0.6601 0.7283 0.029 Uiso calc R 1 1
C C4 0.25391(18) 0.93031(17) 0.54794(16) 0.0263(2) Uani d . 1 1
H H4 0.2494 1.0026 0.6329 0.032 Uiso calc R 1 1
C C5 0.26641(18) 1.02541(16) 0.36935(16) 0.0258(2) Uani d . 1 1
H H5 0.2713 1.1640 0.3288 0.031 Uiso calc R 1 1
C C6 0.28268(19) 0.62276(17) 0.15235(15) 0.0247(2) Uani d . 1 1
H H6A 0.4087 0.5441 0.1314 0.030 Uiso calc R 1 1
H H6B 0.1578 0.5329 0.1981 0.030 Uiso calc R 1 1
Cl Cl1 0.81001(5) 0.75715(4) 0.07668(4) 0.03225(11) Uani d . 1 1
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 0.0459(5) 0.0196(4) 0.0218(4) 0.0029(3) -0.0161(4) -0.0034(3)
O2 0.0412(5) 0.0395(5) 0.0163(4) 0.0019(4) -0.0116(4) -0.0050(3)
N1 0.0253(5) 0.0228(4) 0.0162(4) 0.0008(3) -0.0081(3) -0.0013(3)
C1 0.0195(5) 0.0229(5) 0.0166(5) 0.0015(4) -0.0069(4) -0.0049(4)
C2 0.0221(5) 0.0210(5) 0.0183(5) 0.0018(4) -0.0086(4) -0.0038(4)
C3 0.0299(5) 0.0269(5) 0.0181(5) 0.0016(4) -0.0118(4) -0.0054(4)
C4 0.0305(6) 0.0271(5) 0.0253(5) 0.0010(4) -0.0119(4) -0.0111(4)
C5 0.0292(5) 0.0202(5) 0.0279(6) 0.0005(4) -0.0108(4) -0.0056(4)
C6 0.0306(6) 0.0278(5) 0.0173(5) 0.0025(4) -0.0096(4) -0.0074(4)
Cl1 0.03770(18) 0.02940(16) 0.02636(16) -0.00094(11) -0.01668(13) 0.00473(11)
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'
Cl Cl 0.1484 0.1585 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 O1 H81 108.9(14)
C6 O2 H82 100.9(13)
C1 N1 C5 123.99(10)
C1 N1 H71 118.0(11)
C5 N1 H71 118.0(11)
N1 C1 C2 118.46(10)
N1 C1 C6 119.00(9)
C2 C1 C6 122.52(10)
O1 C2 C3 124.70(10)
O1 C2 C1 115.98(9)
C3 C2 C1 119.32(10)
C2 C3 C4 119.61(10)
C2 C3 H3 120.2
C4 C3 H3 120.2
C5 C4 C3 119.70(10)
C5 C4 H4 120.1
C3 C4 H4 120.1
N1 C5 C4 118.92(10)
N1 C5 H5 120.5
C4 C5 H5 120.5
O2 C6 C1 111.08(9)
O2 C6 H6A 109.4
C1 C6 H6A 109.4
O2 C6 H6B 109.4
C1 C6 H6B 109.4
H6A C6 H6B 108.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C2 1.3482(13)
O1 H81 0.79(2)
O2 C6 1.4085(13)
O2 H82 0.85(2)
N1 C1 1.3355(14)
N1 C5 1.3470(15)
N1 H71 0.853(17)
C1 C2 1.3948(14)
C1 C6 1.5025(14)
C2 C3 1.3866(15)
C3 C4 1.3921(16)
C3 H3 0.9500
C4 C5 1.3692(16)
C4 H4 0.9500
C5 H5 0.9500
C6 H6A 0.9900
C6 H6B 0.9900
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 H81 Cl1 2_666 0.79(2) 2.22(2) 3.0086(9) 176.1(19)
O2 H82 Cl1 1_455 0.85(2) 2.29(2) 3.1276(11) 168.7(18)
N1 H71 Cl1 2_675 0.853(17) 2.391(17) 3.1739(10) 152.9(14)
C3 H3 O2 1_556 0.95 2.47 3.2069(14) 134.2
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
C5 N1 C1 C2 0.71(16)
C5 N1 C1 C6 -177.70(10)
N1 C1 C2 O1 -179.96(9)
C6 C1 C2 O1 -1.61(15)
N1 C1 C2 C3 -0.18(15)
C6 C1 C2 C3 178.17(10)
O1 C2 C3 C4 179.49(11)
C1 C2 C3 C4 -0.27(17)
C2 C3 C4 C5 0.23(18)
C1 N1 C5 C4 -0.76(17)
C3 C4 C5 N1 0.26(17)
N1 C1 C6 O2 -1.18(14)
C2 C1 C6 O2 -179.52(10)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 2341290
