#------------------------------------------------------------------------------
#$Date: 2017-10-13 10:03:29 +0200 (vie 13 de oct de 2017) $
#$Revision: 201974 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/24/2212477.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_2212477
loop_
_publ_author_name
'Chrzanowski, Lars S. von'
'Lutz, Martin'
'Spek, Anthony L.'
'McDonald, Aidan R.'
'Klink, Gerard P. M. van'
'Koten, Gerard van'
_publ_section_title
;
 2-Carboxy-4-(hydroxymethyl)pyridinium chloride hemihydrate
;
_journal_coeditor_code           BT2257
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1121
_journal_page_last               o1122
_journal_paper_doi               10.1107/S1600536807004941
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C7 H8 N O3 + , Cl - , 0.5H2 O'
_chemical_formula_moiety         'C7 H8 N O3 + , Cl - , 0.5H2 O'
_chemical_formula_sum            'C7 H9 Cl N O3.5'
_chemical_formula_weight         198.60
_chemical_name_systematic
;
2-Carboxy-4-(hydroxymethyl)pyridinium chloride hemihydrate
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 98.990(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   8.1935(4)
_cell_length_b                   13.5699(6)
_cell_length_c                   15.5198(15)
_cell_measurement_reflns_used    22552
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      34.99
_cell_measurement_theta_min      2.65
_cell_volume                     1704.4(2)
_computing_cell_refinement       'PEAKREF (Schreurs, 2005)'
_computing_data_collection       'COLLECT (Nonius, 1999)'
_computing_data_reduction        'EVALCCD (Duisenberg et al.,  2003)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      110(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Nonius KappaCCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_av_sigmaI/netI    0.0105
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            40008
_diffrn_reflns_theta_full        35.00
_diffrn_reflns_theta_max         35.00
_diffrn_reflns_theta_min         2.66
_exptl_absorpt_coefficient_mu    0.421
_exptl_absorpt_correction_T_max  0.90
_exptl_absorpt_correction_T_min  0.83
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2002)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.548
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.24
_refine_diff_density_max         1.125
_refine_diff_density_min         -0.699
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         3753
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0353
_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)+(0.0525P)²+1.7395P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0955
_refine_ls_wR_factor_ref         0.1008
_reflns_number_gt                3274
_reflns_number_total             3753
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt2257.cif
_cod_data_source_block           I
_cod_original_cell_volume        1704.36(19)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_original_formula_sum        'C7 H9 Cl N O3.50'
_cod_database_code               2212477
_cod_database_fobs_code          2212477
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
O O1 0.07702(10) 0.65605(5) 0.01642(4) 0.01750(14) Uani d . 1
H H1O 0.039(3) 0.7105(17) -0.0088(15) 0.045(6) Uiso d . 1
O O2 0.04751(10) 0.72276(5) 0.14613(4) 0.01725(13) Uani d . 1
O O3 0.20061(9) 0.51296(5) 0.41022(4) 0.01373(12) Uani d . 1
H H3O 0.271(2) 0.5546(13) 0.4149(11) 0.027(4) Uiso d . 1
N N1 0.21100(9) 0.49412(5) 0.08935(4) 0.01117(12) Uani d . 1
H H1N 0.205(2) 0.5040(12) 0.0321(11) 0.020(4) Uiso d . 1
C C1 0.16738(10) 0.56437(6) 0.14237(5) 0.01002(13) Uani d . 1
C C2 0.18607(10) 0.54898(6) 0.23129(5) 0.01064(13) Uani d . 1
H H2 0.156(2) 0.6001(12) 0.2676(10) 0.019(4) Uiso d . 1
C C3 0.24403(10) 0.45802(6) 0.26538(5) 0.01114(13) Uani d . 1
C C4 0.29005(12) 0.38698(7) 0.20857(5) 0.01382(14) Uani d . 1
H H4 0.331(2) 0.3246(12) 0.2283(11) 0.020(4) Uiso d . 1
C C5 0.27348(11) 0.40721(6) 0.12035(5) 0.01329(14) Uani d . 1
H H5 0.301(2) 0.3640(13) 0.0794(11) 0.021(4) Uiso d . 1
C C6 0.09164(11) 0.65739(6) 0.10211(5) 0.01143(13) Uani d . 1
C C7 0.25194(12) 0.43389(7) 0.36075(5) 0.01484(15) Uani d . 1
H H7A 0.365(2) 0.4128(13) 0.3865(11) 0.027(4) Uiso d . 1
H H7B 0.175(2) 0.3804(12) 0.3661(11) 0.023(4) Uiso d . 1
Cl Cl1 0.47957(3) 0.656638(19) 0.429264(16) 0.02286(7) Uani d . 1
O O4 0.5000 0.76419(11) 0.2500 0.0395(3) Uani d S 1
H H4O 0.4885 0.7241 0.2934 0.050 Uiso d . 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 0.0313(4) 0.0143(3) 0.0072(2) 0.0086(2) 0.0040(2) 0.0027(2)
O2 0.0284(3) 0.0120(3) 0.0116(3) 0.0045(2) 0.0039(2) -0.0017(2)
O3 0.0209(3) 0.0136(3) 0.0074(2) -0.0008(2) 0.0044(2) -0.00112(19)
N1 0.0163(3) 0.0115(3) 0.0060(2) 0.0023(2) 0.0029(2) 0.0003(2)
C1 0.0139(3) 0.0097(3) 0.0067(3) 0.0006(2) 0.0023(2) 0.0002(2)
C2 0.0147(3) 0.0110(3) 0.0065(3) 0.0006(2) 0.0026(2) 0.0000(2)
C3 0.0151(3) 0.0120(3) 0.0064(3) 0.0010(2) 0.0023(2) 0.0007(2)
C4 0.0213(4) 0.0127(3) 0.0079(3) 0.0042(3) 0.0034(3) 0.0012(2)
C5 0.0200(4) 0.0122(3) 0.0081(3) 0.0043(3) 0.0036(3) 0.0004(2)
C6 0.0162(3) 0.0102(3) 0.0080(3) 0.0006(2) 0.0022(2) 0.0008(2)
C7 0.0252(4) 0.0135(3) 0.0063(3) 0.0029(3) 0.0039(3) 0.0010(2)
Cl1 0.03037(13) 0.01878(11) 0.01996(11) -0.00810(8) 0.00561(9) -0.00835(8)
O4 0.0639(10) 0.0283(6) 0.0299(7) 0.000 0.0183(7) 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'
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
C6 O1 H1O 114.3(15)
C7 O3 H3O 108.0(13)
C1 N1 C5 121.74(7)
C1 N1 H1N 121.6(10)
C5 N1 H1N 116.6(10)
N1 C1 C2 120.42(7)
N1 C1 C6 118.33(7)
C2 C1 C6 121.21(7)
C1 C2 C3 119.38(7)
C1 C2 H2 118.9(10)
C3 C2 H2 121.7(10)
C2 C3 C4 118.68(7)
C2 C3 C7 121.60(7)
C4 C3 C7 119.68(7)
C5 C4 C3 119.57(8)
C5 C4 H4 118.4(10)
C3 C4 H4 122.1(10)
N1 C5 C4 120.12(8)
N1 C5 H5 115.7(11)
C4 C5 H5 124.2(11)
O2 C6 O1 126.37(8)
O2 C6 C1 121.54(7)
O1 C6 C1 112.07(7)
O3 C7 C3 113.30(7)
O3 C7 H7A 109.7(10)
C3 C7 H7A 110.7(10)
O3 C7 H7B 105.6(10)
C3 C7 H7B 108.5(10)
H7A C7 H7B 108.8(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C6 1.3166(10)
O1 H1O 0.87(2)
O2 C6 1.2090(10)
O3 C7 1.4208(11)
O3 H3O 0.805(18)
N1 C1 1.3436(10)
N1 C5 1.3444(11)
N1 H1N 0.893(17)
C1 C2 1.3804(11)
C1 C6 1.4992(11)
C2 C3 1.3966(12)
C2 H2 0.953(16)
C3 C4 1.3974(12)
C3 C7 1.5074(11)
C4 C5 1.3821(11)
C4 H4 0.943(17)
C5 H5 0.918(17)
C7 H7A 0.990(18)
C7 H7B 0.971(17)
O4 H4O 0.8822
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
N1 H1N O1 . 0.893(17) 2.309(16) 2.6318(10) 101.1(12)
N1 H1N O3 6_565 0.893(17) 1.900(17) 2.7697(9) 164.2(15)
O1 H1O Cl1 8_465 0.87(2) 2.06(2) 2.9309(7) 173(2)
O3 H3O Cl1 . 0.805(18) 2.181(18) 2.9836(7) 174.7(17)
O4 H4O Cl1 . 0.88 2.31 3.1692(8) 165
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 0.10(13)
C5 N1 C1 C6 -177.30(8)
N1 C1 C2 C3 -2.78(12)
C6 C1 C2 C3 174.54(8)
C1 C2 C3 C4 3.47(13)
C1 C2 C3 C7 -174.27(8)
C2 C3 C4 C5 -1.59(13)
C7 C3 C4 C5 176.20(9)
C1 N1 C5 C4 1.85(14)
C3 C4 C5 N1 -1.06(14)
N1 C1 C6 O2 178.89(9)
C2 C1 C6 O2 1.51(13)
N1 C1 C6 O1 0.58(11)
C2 C1 C6 O1 -176.80(8)
C2 C3 C7 O3 -1.93(12)
C4 C3 C7 O3 -179.65(8)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21125254
