#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/33/2213354.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_2213354
loop_
_publ_author_name
'Tsonko Kolev'
'Boris Shivachev'
'Rosica Petrova'
_publ_section_title
;
 4-Phenylpyridinium 3-carboxy-2,3-dihydroxypropanoate dihydrate
;
_journal_coeditor_code           HB2365
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2511
_journal_page_last               o2511
_journal_paper_doi               10.1107/S1600536807017217
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C11 H10 N + , C4 H5 O6 - , 2H2 O'
_chemical_formula_moiety         'C11 H10 N + , C4 H5 O6 - , 2H2 O'
_chemical_formula_sum            'C15 H19 N O8'
_chemical_formula_weight         341.31
_chemical_name_common
'4-phenylpyridinium hydrogentartrate dihydrate'
_chemical_name_systematic
;
4-Phenylpyridinium 3-carboxy-2,3-dihydroxypropanoate dihydrate
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.3051(16)
_cell_length_b                   11.850(2)
_cell_length_c                   18.165(3)
_cell_measurement_reflns_used    22
_cell_measurement_temperature    290(2)
_cell_measurement_theta_max      19.48
_cell_measurement_theta_min      18.09
_cell_volume                     1572.5(5)
_computing_cell_refinement       'CAD-4 EXPRESS'
_computing_data_collection       'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al.,
2006)
;
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      290(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       'nonprofiled ω/2θ'
_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  0.0484
_diffrn_reflns_av_sigmaI/netI    0.0595
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            4241
_diffrn_reflns_theta_full        27.97
_diffrn_reflns_theta_max         27.97
_diffrn_reflns_theta_min         2.05
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   none
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    none
_exptl_crystal_description       prism
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.197
_refine_ls_extinction_coef       none
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.940
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2180
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.940
_refine_ls_R_factor_all          0.0893
_refine_ls_R_factor_gt           0.0454
_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)+(0.0534P)²+0.3826P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1011
_refine_ls_wR_factor_ref         0.1192
_reflns_number_gt                1406
_reflns_number_total             2180
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb2365.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not meaured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_formula_sum        'C15 H19 N O8 '
_cod_database_code               2213354
_cod_database_fobs_code          2213354
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, 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
C C1 -0.0051(4) 0.2771(3) 0.86282(19) 0.0299(7) Uani d . 1
C C2 0.2041(4) 0.2727(3) 0.86494(19) 0.0316(7) Uani d . 1
H H2 0.2412 0.2212 0.9044 0.038 Uiso calc R 1
C C3 0.2900(4) 0.3865(3) 0.87922(19) 0.0321(8) Uani d . 1
H H3 0.2611 0.4094 0.9297 0.039 Uiso calc R 1
C C4 0.4989(4) 0.3800(3) 0.8712(2) 0.0314(8) Uani d . 1
C C212 0.4524(5) 0.1070(3) 0.4994(2) 0.0425(9) Uani d . 1
H H212 0.4797 0.0937 0.5487 0.051 Uiso calc R 1
C C211 0.4563(6) 0.0194(3) 0.4502(2) 0.0475(10) Uani d . 1
H H211 0.4901 -0.0523 0.4658 0.057 Uiso calc R 1
C C210 0.4095(6) 0.0378(4) 0.3768(2) 0.0513(10) Uani d . 1
H H210 0.4093 -0.0218 0.3435 0.062 Uiso calc R 1
C C29 0.3640(6) 0.1439(3) 0.3542(2) 0.0495(11) Uani d . 1
H H29 0.3332 0.1561 0.3052 0.059 Uiso calc R 1
C C28 0.3629(5) 0.2332(3) 0.4027(2) 0.0422(9) Uani d . 1
H H28 0.3321 0.3052 0.3864 0.051 Uiso calc R 1
C C27 0.4084(5) 0.2152(3) 0.47646(18) 0.0372(8) Uani d . 1
C C24 0.4095(5) 0.3097(3) 0.52912(18) 0.0361(8) Uani d . 1
C C23 0.4631(5) 0.4188(3) 0.5084(2) 0.0415(9) Uani d . 1
H H23 0.5000 0.4327 0.4603 0.050 Uiso calc R 1
C C22 0.4616(5) 0.5052(3) 0.5587(2) 0.0469(10) Uani d . 1
H H22 0.4957 0.5777 0.5447 0.056 Uiso calc R 1
C C26 0.3556(6) 0.3821(4) 0.6505(2) 0.0497(10) Uani d . 1
H H26 0.3179 0.3716 0.6989 0.060 Uiso calc R 1
C C25 0.3547(5) 0.2934(4) 0.6024(2) 0.0453(10) Uani d . 1
H H25 0.3178 0.2223 0.6182 0.054 Uiso calc R 1
N N21 0.4108(5) 0.4841(3) 0.62782(18) 0.0476(8) Uani d . 1
H H21N 0.4137 0.5384 0.6592 0.057 Uiso calc R 1
O O11 -0.0810(3) 0.2321(2) 0.81114(14) 0.0473(7) Uani d . 1
O O12 -0.0837(3) 0.3244(2) 0.91785(12) 0.0418(6) Uani d . 1
O O21 0.2725(3) 0.2304(2) 0.79728(14) 0.0447(7) Uani d . 1
H H21 0.1936 0.1919 0.7773 0.067 Uiso calc R 1
O O31 0.2197(3) 0.4688(2) 0.83042(15) 0.0454(7) Uani d . 1
H H31 0.2690 0.5297 0.8386 0.068 Uiso calc R 1
O O41 0.5784(3) 0.3136(2) 0.91606(13) 0.0426(6) Uani d . 1
H H41 0.6889 0.3138 0.9080 0.064 Uiso calc R 1
O O42 0.5708(3) 0.4383(2) 0.82451(16) 0.0525(7) Uani d . 1
O OW1 0.1312(4) 0.0776(2) 0.69310(15) 0.0504(7) Uani d . 1
H HW1A 0.2112 0.0176 0.6874 0.060 Uiso d R 1
H HW1B 0.0527 0.0275 0.7042 0.060 Uiso d R 1
O OW2 0.3906(3) 0.63832(19) 0.73677(14) 0.0460(7) Uani d . 1
H HW2A 0.4742 0.6829 0.7300 0.055 Uiso d R 1
H HW2B 0.3184 0.6762 0.7245 0.055 Uiso d R 1
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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
0 3 -5
-1 4 -1
1 2 6
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
O11 C1 O12 126.2(3) ?
O11 C1 C2 117.4(3) n
O12 C1 C2 116.3(3) n
O21 C2 C3 108.6(3) ?
O21 C2 C1 110.0(3) ?
C3 C2 C1 112.9(3) n
O21 C2 H2 108.4 ?
C3 C2 H2 108.4 ?
C1 C2 H2 108.4 ?
O31 C3 C2 110.9(3) ?
O31 C3 C4 109.6(3) n
C2 C3 C4 110.6(3) ?
O31 C3 H3 108.5 ?
C2 C3 H3 108.5 ?
C4 C3 H3 108.5 ?
O42 C4 O41 127.0(3) ?
O42 C4 C3 118.0(3) ?
O41 C4 C3 115.0(3) ?
C211 C212 C27 120.6(3) n
C211 C212 H212 119.7 ?
C27 C212 H212 119.7 ?
C212 C211 C210 120.1(4) ?
C212 C211 H211 120.0 ?
C210 C211 H211 120.0 ?
C29 C210 C211 119.4(4) ?
C29 C210 H210 120.3 ?
C211 C210 H210 120.3 ?
C210 C29 C28 121.3(4) ?
C210 C29 H29 119.4 ?
C28 C29 H29 119.4 ?
C29 C28 C27 119.6(4) ?
C29 C28 H28 120.2 ?
C27 C28 H28 120.2 ?
C212 C27 C28 119.0(4) ?
C212 C27 C24 120.5(3) ?
C28 C27 C24 120.5(3) ?
C23 C24 C25 117.5(3) ?
C23 C24 C27 121.9(3) ?
C25 C24 C27 120.6(3) ?
C22 C23 C24 120.5(3) ?
C22 C23 H23 119.7 ?
C24 C23 H23 119.7 ?
N21 C22 C23 119.3(4) n
N21 C22 H22 120.4 ?
C23 C22 H22 120.4 ?
N21 C26 C25 119.9(4) ?
N21 C26 H26 120.1 ?
C25 C26 H26 120.1 ?
C26 C25 C24 120.0(4) ?
C26 C25 H25 120.0 ?
C24 C25 H25 120.0 ?
C22 N21 C26 122.9(4) n
C22 N21 H21N 118.6 n
C26 N21 H21N 118.6 ?
C2 O21 H21 109.5 ?
C3 O31 H31 109.5 ?
C4 O41 H41 109.5 ?
HW1A OW1 HW1B 85.2 ?
HW2A OW2 HW2B 95.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O11 1.213(4) n
C1 O12 1.282(4) n
C1 C2 1.530(4) ?
C2 O21 1.419(4) n
C2 C3 1.510(5) ?
C2 H2 0.9800 ?
C3 O31 1.415(4) n
C3 C4 1.535(4) n
C3 H3 0.9800 ?
C4 O42 1.213(4) n
C4 O41 1.273(4) n
C212 C211 1.370(6) ?
C212 C27 1.386(5) n
C212 H212 0.9300 ?
C211 C210 1.394(6) ?
C211 H211 0.9300 ?
C210 C29 1.363(6) ?
C210 H210 0.9300 ?
C29 C28 1.377(5) ?
C29 H29 0.9300 ?
C28 C27 1.398(5) n
C28 H28 0.9300 ?
C27 C24 1.473(5) n
C24 C23 1.402(5) n
C24 C25 1.403(5) n
C23 C22 1.372(5) ?
C23 H23 0.9300 ?
C22 N21 1.333(5) n
C22 H22 0.9300 ?
C26 N21 1.339(5) n
C26 C25 1.367(5) ?
C26 H26 0.9300 ?
C25 H25 0.9300 ?
N21 H21N 0.8600 ?
O21 H21 0.8200 ?
O31 H31 0.8200 ?
O41 H41 0.8200 ?
OW1 HW1A 0.9258 ?
OW1 HW1B 0.8495 ?
OW2 HW2A 0.8170 ?
OW2 HW2B 0.7278 ?
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
N21 H21N OW2 . 0.86 1.85 2.698(4) 169 yes
O21 H21 O11 . 0.82 2.15 2.595(3) 114 yes
O21 H21 OW1 . 0.82 2.09 2.815(3) 147 yes
O31 H31 OW2 . 0.82 2.42 2.913(3) 119 yes
O41 H41 O12 1_655 0.82 1.68 2.472(3) 163 yes
OW1 HW1B O31 4_546 0.85 2.20 2.901(3) 140 yes
OW1 HW1A O42 4_646 0.93 1.86 2.750(4) 160 yes
OW2 HW2A O21 4_656 0.82 2.00 2.762(3) 156 yes
OW2 HW2B O11 4_556 0.73 1.97 2.666(3) 161 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
_geom_torsion_publ_flag
C23 C22 N21 C26 -1.9(6) ?
N21 C22 C23 C24 0.9(6) ?
C22 C23 C24 C25 0.1(5) ?
C22 C23 C24 C27 179.6(3) ?
C23 C24 C25 C26 -0.2(5) ?
C27 C24 C25 C26 -179.7(4) ?
C23 C24 C27 C28 -34.9(6) n
C23 C24 C27 C212 145.1(4) n
C25 C24 C27 C28 144.6(4) n
C25 C24 C27 C212 -35.4(6) ?
C24 C25 C26 N21 -0.8(6) n
C25 C26 N21 C22 1.9(6) ?
C24 C27 C28 C29 179.5(4) ?
C212 C27 C28 C29 -0.5(6) ?
C27 C28 C29 C210 -0.3(6) ?
C211 C210 C29 C28 -0.2(7) ?
C29 C210 C211 C212 1.5(7) ?
C210 C211 C212 C27 -2.2(6) ?
C211 C212 C27 C24 -178.3(3) ?
C211 C212 C27 C28 1.7(6) ?
O11 C1 C2 O21 9.5(5) ?
O11 C1 C2 C3 130.9(3) ?
O12 C1 C2 O21 -173.3(3) ?
O12 C1 C2 C3 -51.8(4) ?
O21 C2 C3 O31 71.2(3) ?
O21 C2 C3 C4 -50.6(4) ?
C1 C2 C3 O31 -51.0(4) ?
C1 C2 C3 C4 -172.9(3) ?
O31 C3 C4 O41 175.6(3) ?
O31 C3 C4 O42 -3.4(5) ?
C2 C3 C4 O41 -61.8(4) ?
C2 C3 C4 O42 119.2(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21185147
