#------------------------------------------------------------------------------
#$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2008999.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_2008999
loop_
_publ_author_name
'Freytag, M.'
'Jones, P. G.'
_publ_section_title
;
 2-Chloro-6-hydroxypyridinium chloride hydrate
;
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1682
_journal_page_last               1685
_journal_volume                  55
_journal_year                    1999
_chemical_formula_moiety         'C5 H5 Cl N O 1+, Cl 1-, H2 O'
_chemical_formula_sum            'C5 H7 Cl2 N O2'
_chemical_formula_weight         184.02
_chemical_name_systematic
;
 2-Chloro-6-hydroxypyridinium Chloride Hydrate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 104.662(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.3471(10)
_cell_length_b                   7.9330(12)
_cell_length_c                   13.6630(16)
_cell_measurement_reflns_used    63
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      12.3
_cell_measurement_theta_min      4.7
_cell_volume                     770.41(18)
_computing_cell_refinement       XSCANS
_computing_data_collection       'XSCANS (Siemens, 1991)'
_computing_data_reduction        XSCANS
_computing_molecular_graphics    'XP (Siemens, 1994b)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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    0.0427
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            3022
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         3.08
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 247
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.780
_exptl_absorpt_correction_T_max  0.965
_exptl_absorpt_correction_T_min  0.861
_exptl_absorpt_correction_type   '\y scan'
_exptl_absorpt_process_details   '(XEMP; Siemens, 1994a)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.587
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.31
_refine_diff_density_min         -0.21
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.885
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     107
_refine_ls_number_reflns         1770
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.885
_refine_ls_R_factor_all          0.046
_refine_ls_R_factor_gt           0.028
_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^)+(0.0342P)^2^] where P = (Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.065
_reflns_number_gt                1302
_reflns_number_total             1770
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    bm1350.cif
_[local]_cod_data_source_block   sesto
_[local]_cod_cif_authors_sg_H-M  'P 21/c'
_cod_database_code               2008999
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
Cl1 0.81785(7) 0.82484(6) 0.39255(3) 0.02877(13) Uani d . 1 Cl
Cl2 0.82620(7) 0.96547(6) 0.66321(3) 0.02662(13) Uani d . 1 Cl
O 0.3631(2) 0.78107(18) 0.58993(10) 0.0288(3) Uani d . 1 O
H6 0.262(4) 0.738(4) 0.601(2) 0.066(9) Uiso d . 1 H
N 0.5549(2) 0.78332(19) 0.48710(11) 0.0203(3) Uani d . 1 N
H1 0.630(3) 0.848(3) 0.5344(16) 0.029(6) Uiso d . 1 H
C2 0.6089(3) 0.7403(2) 0.40262(13) 0.0218(4) Uani d . 1 C
C3 0.5022(3) 0.6349(2) 0.33238(13) 0.0265(4) Uani d . 1 C
H3 0.5396 0.6043 0.2731 0.032 Uiso calc R 1 H
C4 0.3355(3) 0.5735(2) 0.35060(14) 0.0277(4) Uani d . 1 C
H4 0.2583 0.5001 0.3026 0.033 Uiso calc R 1 H
C5 0.2805(3) 0.6167(2) 0.43642(14) 0.0237(4) Uani d . 1 C
H5 0.1679 0.5727 0.4485 0.028 Uiso calc R 1 H
C6 0.3942(3) 0.7268(2) 0.50534(12) 0.0211(4) Uani d . 1 C
O1W 0.0781(2) 0.6667(2) 0.63601(11) 0.0284(3) Uani d . 1 O
H01 0.008(4) 0.755(4) 0.644(2) 0.070(9) Uiso d . 1 H
H02 0.113(4) 0.611(4) 0.690(2) 0.059(8) Uiso d . 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
Cl1 0.0281(3) 0.0341(3) 0.0274(2) -0.0004(2) 0.01302(19) 0.0033(2)
Cl2 0.0277(3) 0.0285(2) 0.0237(2) -0.0022(2) 0.00666(18) -0.00369(19)
O 0.0304(8) 0.0338(8) 0.0263(7) -0.0040(7) 0.0145(6) -0.0086(6)
N 0.0222(8) 0.0205(8) 0.0180(7) 0.0005(7) 0.0047(6) -0.0008(6)
C2 0.0243(10) 0.0232(9) 0.0188(8) 0.0046(8) 0.0071(7) 0.0049(7)
C3 0.0298(11) 0.0314(11) 0.0188(9) 0.0037(8) 0.0072(8) -0.0003(7)
C4 0.0294(11) 0.0267(10) 0.0236(9) 0.0013(8) 0.0005(8) -0.0049(8)
C5 0.0221(10) 0.0223(9) 0.0267(9) 0.0004(8) 0.0060(8) -0.0001(8)
C6 0.0232(10) 0.0201(9) 0.0198(8) 0.0047(7) 0.0052(7) 0.0022(7)
O1W 0.0299(8) 0.0318(8) 0.0251(7) 0.0033(7) 0.0101(6) 0.0055(6)
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
_geom_angle_publ_flag
C6 N C2 122.30(16) y
N C2 C3 120.91(17) y
N C2 Cl1 115.57(14) y
C3 C2 Cl1 123.51(14) y
C2 C3 C4 117.59(17) y
C5 C4 C3 121.59(18) y
C4 C5 C6 118.42(18) y
O C6 N 114.36(16) y
O C6 C5 126.45(18) y
N C6 C5 119.17(16) y
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C2 1.712(2) y
O C6 1.307(2) y
N C6 1.344(2) y
N C2 1.356(2) y
C2 C3 1.362(3) y
C3 C4 1.398(3) y
C4 C5 1.377(3) y
C5 C6 1.396(3) y
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 Cl2 . 0.90(2) 2.18(2) 3.0698(16) 170.3(18) y
O H6 O1W . 0.86(3) 1.65(3) 2.504(2) 172(3) y
O1W H01 Cl2 1_455 0.90(3) 2.19(3) 3.0870(17) 178(3) y
O1W H02 Cl2 2_646 0.84(3) 2.26(3) 3.0969(16) 173(3) y
C3 H3 Cl2 4_575 0.95 2.93 3.799(2) 152.3 y
C3 H3 O 4_575 0.95 2.67 3.278(2) 122.3 y
C4 H4 Cl1 2_645 0.95 2.93 3.782(2) 149.5 y
C5 H5 O1W 3_566 0.95 2.67 3.414(2) 135.2 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
C6 N C2 C3 -0.8(3)
C6 N C2 Cl1 179.96(13)
N C2 C3 C4 0.1(3)
Cl1 C2 C3 C4 179.29(14)
C2 C3 C4 C5 -0.2(3)
C3 C4 C5 C6 1.0(3)
C2 N C6 O -179.68(16)
C2 N C6 C5 1.6(3)
C4 C5 C6 O 179.78(17)
C4 C5 C6 N -1.6(3)