#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/80/2238060.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_2238060
loop_
_publ_author_name
'Seethalakshmi, T.'
'Manivannan, S.'
'Dhanuskodi, S.'
'Lynch, Daniel E.'
'Thamotharan, S.'
_publ_section_title
;
 4-Hydroxy-1,2,6-trimethylpyridinium bromide monohydrate
;
_journal_coeditor_code           TK5224
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o941
_journal_page_last               o942
_journal_paper_doi               10.1107/S1600536813013330
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C8 H12 N O +, Br -, H2 O'
_chemical_formula_moiety         'C8 H12 N O +, Br -, H2 O'
_chemical_formula_sum            'C8 H14 Br N O2'
_chemical_formula_weight         236.11
_chemical_name_systematic
;
4-Hydroxy-1,2,6-trimethylpyridinium bromide monohydrate
;
_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'
_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                 99.504(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.4796(4)
_cell_length_b                   8.5874(6)
_cell_length_c                   13.8479(9)
_cell_measurement_reflns_used    2311
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1
_cell_volume                     994.53(11)
_computing_cell_refinement       'DENZO (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1998)'
_computing_data_reduction        'DENZO (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'isomorphous method'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type
'Bruker--Nonius 95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker--Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_av_sigmaI/netI    0.0314
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11830
_diffrn_reflns_theta_full        27.53
_diffrn_reflns_theta_max         27.53
_diffrn_reflns_theta_min         2.80
_exptl_absorpt_coefficient_mu    4.097
_exptl_absorpt_correction_T_max  0.4274
_exptl_absorpt_correction_T_min  0.3729
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.577
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.585
_refine_diff_density_min         -0.344
_refine_ls_extinction_coef       0.0025(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     125
_refine_ls_number_reflns         2277
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0261
_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)+(0.0179P)²+0.9223P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0525
_refine_ls_wR_factor_ref         0.0561
_reflns_number_gt                1888
_reflns_number_total             2277
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tk5224.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2238060
_cod_database_fobs_code          2238060
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_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
Br Br1 0.46272(3) 0.08691(3) 0.252474(16) 0.02160(9) Uani d . 1 1
O O1 0.8002(2) -0.29194(18) 0.48421(13) 0.0265(4) Uani d D 1 1
O O1W 0.3258(2) 0.3759(2) 0.36438(13) 0.0270(4) Uani d D 1 1
N N1 0.7983(2) 0.1745(2) 0.42283(14) 0.0185(4) Uani d . 1 1
C C2 0.7227(2) 0.1241(2) 0.49673(16) 0.0175(4) Uani d . 1 1
C C3 0.7211(3) -0.0319(3) 0.51871(16) 0.0185(5) Uani d . 1 1
H H3 0.6689 -0.0670 0.5703 0.022 Uiso calc R 1 1
C C4 0.7960(3) -0.1390(3) 0.46562(17) 0.0196(5) Uani d . 1 1
C C5 0.8699(3) -0.0850(3) 0.38918(16) 0.0199(5) Uani d . 1 1
H H5 0.9208 -0.1565 0.3519 0.024 Uiso calc R 1 1
C C6 0.8691(2) 0.0712(3) 0.36768(16) 0.0190(5) Uani d . 1 1
C C7 0.9436(3) 0.1302(3) 0.28400(18) 0.0278(5) Uani d . 1 1
H H7A 0.8608 0.1764 0.2346 0.042 Uiso calc R 1 1
H H7B 0.9945 0.0436 0.2548 0.042 Uiso calc R 1 1
H H7C 1.0241 0.2091 0.3078 0.042 Uiso calc R 1 1
C C8 0.7984(3) 0.3436(3) 0.4015(2) 0.0284(6) Uani d . 1 1
H H8A 0.6880 0.3802 0.3832 0.043 Uiso calc R 1 1
H H8B 0.8572 0.3627 0.3474 0.043 Uiso calc R 1 1
H H8C 0.8501 0.3999 0.4598 0.043 Uiso calc R 1 1
C C9 0.6442(3) 0.2398(3) 0.55408(17) 0.0236(5) Uani d . 1 1
H H9A 0.7252 0.3102 0.5889 0.035 Uiso calc R 1 1
H H9B 0.5904 0.1849 0.6015 0.035 Uiso calc R 1 1
H H9C 0.5654 0.3002 0.5094 0.035 Uiso calc R 1 1
H H1 0.756(3) -0.313(3) 0.5317(17) 0.038(9) Uiso d D 1 1
H H1W 0.355(3) 0.309(3) 0.330(2) 0.044(9) Uiso d D 1 1
H H2W 0.261(4) 0.432(3) 0.328(2) 0.062(11) Uiso d 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
Br1 0.02104(13) 0.01973(12) 0.02404(14) -0.00007(9) 0.00380(8) 0.00019(10)
O1 0.0352(10) 0.0132(8) 0.0329(10) 0.0028(7) 0.0108(8) 0.0001(7)
O1W 0.0316(10) 0.0181(9) 0.0307(10) 0.0045(7) 0.0037(8) 0.0019(8)
N1 0.0166(9) 0.0138(9) 0.0242(11) -0.0018(7) 0.0010(7) -0.0019(7)
C2 0.0132(10) 0.0179(11) 0.0201(12) -0.0013(8) -0.0015(8) -0.0028(9)
C3 0.0174(11) 0.0195(11) 0.0181(12) -0.0001(8) 0.0014(9) -0.0010(9)
C4 0.0177(11) 0.0157(10) 0.0240(12) 0.0007(8) -0.0007(9) -0.0013(9)
C5 0.0177(11) 0.0185(10) 0.0229(12) 0.0004(9) 0.0013(9) -0.0044(9)
C6 0.0143(10) 0.0216(11) 0.0203(11) -0.0026(9) 0.0002(8) -0.0021(9)
C7 0.0273(13) 0.0305(13) 0.0268(13) -0.0025(10) 0.0079(10) 0.0022(10)
C8 0.0300(13) 0.0153(11) 0.0407(16) 0.0003(10) 0.0081(11) 0.0041(10)
C9 0.0254(12) 0.0179(11) 0.0268(13) 0.0035(9) 0.0024(9) -0.0033(10)
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'
Br Br -0.2901 2.4595 '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
C4 O1 H1 111(2)
H1W O1W H2W 107(3)
C2 N1 C6 121.01(18)
C2 N1 C8 118.45(19)
C6 N1 C8 120.52(19)
N1 C2 C3 119.9(2)
N1 C2 C9 119.51(19)
C3 C2 C9 120.6(2)
C2 C3 C4 120.3(2)
C2 C3 H3 119.9
C4 C3 H3 119.9
O1 C4 C3 123.1(2)
O1 C4 C5 118.1(2)
C3 C4 C5 118.8(2)
C6 C5 C4 120.1(2)
C6 C5 H5 119.9
C4 C5 H5 119.9
N1 C6 C5 119.8(2)
N1 C6 C7 119.5(2)
C5 C6 C7 120.7(2)
C6 C7 H7A 109.5
C6 C7 H7B 109.5
H7A C7 H7B 109.5
C6 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
N1 C8 H8A 109.5
N1 C8 H8B 109.5
H8A C8 H8B 109.5
N1 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
C2 C9 H9A 109.5
C2 C9 H9B 109.5
H9A C9 H9B 109.5
C2 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C4 1.338(3)
O1 H1 0.828(17)
O1W H1W 0.813(17)
O1W H2W 0.833(18)
N1 C2 1.365(3)
N1 C6 1.372(3)
N1 C8 1.482(3)
C2 C3 1.374(3)
C2 C9 1.496(3)
C3 C4 1.394(3)
C3 H3 0.9500
C4 C5 1.395(3)
C5 C6 1.374(3)
C5 H5 0.9500
C6 C7 1.496(3)
C7 H7A 0.9800
C7 H7B 0.9800
C7 H7C 0.9800
C8 H8A 0.9800
C8 H8B 0.9800
C8 H8C 0.9800
C9 H9A 0.9800
C9 H9B 0.9800
C9 H9C 0.9800
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
O1 H1 O1W 3_656 0.828(17) 1.783(18) 2.607(2) 174(3) yes
O1W H1W Br1 . 0.813(17) 2.436(18) 3.2407(18) 170(3) yes
O1W H2W Br1 2 0.833(18) 2.433(19) 3.2527(18) 168(3) yes
C3 H3 Br1 3_656 0.95 2.86 3.785(2) 164 yes
C5 H5 Br1 2_645 0.95 2.90 3.837(2) 170 yes
C9 H9A Br1 4_666 0.98 2.91 3.822(2) 155 yes
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
C6 N1 C2 C3 2.1(3)
C8 N1 C2 C3 -179.6(2)
C6 N1 C2 C9 -178.86(19)
C8 N1 C2 C9 -0.6(3)
N1 C2 C3 C4 -0.3(3)
C9 C2 C3 C4 -179.33(19)
C2 C3 C4 O1 179.2(2)
C2 C3 C4 C5 -1.0(3)
O1 C4 C5 C6 -179.7(2)
C3 C4 C5 C6 0.4(3)
C2 N1 C6 C5 -2.6(3)
C8 N1 C6 C5 179.2(2)
C2 N1 C6 C7 176.9(2)
C8 N1 C6 C7 -1.4(3)
C4 C5 C6 N1 1.3(3)
C4 C5 C6 C7 -178.1(2)
