#------------------------------------------------------------------------------
#$Date: 2008-02-04 17:24:24 +0000 (Mon, 04 Feb 2008) $
#$Revision: 87 $
#$URL: svn://www.crystallography.net/cod/cif/2/2203709.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2203709
loop_
_publ_author_name
'T. Kolev'
'R. Wortmann'
'M. Spiteller'
'W.S. Sheldrick'
'M. Heller'
_publ_section_title
;
4-Phenylpyridinium hydrogensquarate
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica, Section E'
_journal_page_first              o956
_journal_page_last               o957
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C11 H10 N 1+, C4 H O4 1-'
_chemical_formula_moiety         'C11 H10 N 1+, C4 H O4 1-'
_chemical_formula_sum            'C15 H11 N O4'
_chemical_formula_weight         269.25
_chemical_melting_point          'not measured'
_chemical_name_common            'not relevant'
_chemical_name_systematic
;
4-phenylpyridinium hydrogensquarate
;
_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 21/c'
_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                 113.91(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.781(3)
_cell_length_b                   8.994(2)
_cell_length_c                   12.988(3)
_cell_measurement_reflns_used    57
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      14.6
_cell_measurement_theta_min      7.7
_cell_volume                     1258.0(6)
_computing_cell_refinement       R3m/V
_computing_data_collection       'R3m/V (Siemens, 1989)'
_computing_data_reduction        R3m/V
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1995)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Siemens P4 4-circle'
_diffrn_measurement_method       'Profile fitted'
_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  0.0356
_diffrn_reflns_av_sigmaI/netI    0.0445
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            2323
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.95
_diffrn_standards_decay_%        20
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  0.96335
_exptl_absorpt_correction_T_min  0.93331
_exptl_absorpt_correction_type   Psi-scan
_exptl_absorpt_process_details   '(XPREP in SHELXTL; Sheldrick, 1995)'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.39
_refine_diff_density_max         0.130
_refine_diff_density_min         -0.145
_refine_ls_extinction_coef       0.0040(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         2211
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0792
_refine_ls_R_factor_gt           0.0425
_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^)+(0.0421P)^2^+0.1558P] where P = (Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0883
_refine_ls_wR_factor_ref         0.0998
_reflns_number_gt                1494
_reflns_number_total             2211
_reflns_threshold_expression     I>2s(I)
_[local]_cod_original_file       bt6456.cif
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_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'
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
C1' 0.65062(19) 0.1383(2) 0.55178(18) 0.0407(5) Uani d . 1 C
O1' 0.72770(15) 0.06059(17) 0.53774(14) 0.0564(5) Uani d . 1 O
C2' 0.60127(19) 0.2910(2) 0.51886(18) 0.0390(5) Uani d . 1 C
O2' 0.62390(15) 0.39071(18) 0.46260(14) 0.0578(5) Uani d . 1 O
C3' 0.52158(18) 0.2703(2) 0.57592(17) 0.0379(5) Uani d . 1 C
O3' 0.43808(15) 0.34715(18) 0.59577(14) 0.0517(4) Uani d . 1 O
H3' 0.426(3) 0.452(4) 0.565(3) 0.124(12) Uiso d . 1 H
C4' 0.56442(18) 0.1233(2) 0.60989(16) 0.0363(5) Uani d . 1 C
O4' 0.53924(14) 0.02461(16) 0.66420(13) 0.0494(4) Uani d . 1 O
N1 0.34944(17) 0.07817(19) 0.72465(15) 0.0439(5) Uani d . 1 N
H1 0.4051 0.0651 0.6985 0.061(8) Uiso calc R 1 H
C2 0.2686(2) -0.0300(2) 0.71432(19) 0.0472(6) Uani d . 1 C
H2 0.2726 -0.1181 0.6785 0.049(6) Uiso calc R 1 H
C3 0.1798(2) -0.0131(2) 0.75576(18) 0.0443(6) Uani d . 1 C
H3 0.1242 -0.0899 0.7484 0.042(6) Uiso calc R 1 H
C4 0.17211(18) 0.1194(2) 0.80922(16) 0.0369(5) Uani d . 1 C
C5 0.25842(18) 0.2292(2) 0.81717(18) 0.0407(5) Uani d . 1 C
H5 0.2566 0.3191 0.8518 0.054(7) Uiso calc R 1 H
C6 0.3460(2) 0.2064(2) 0.77461(18) 0.0435(6) Uani d . 1 C
H6 0.4033 0.2807 0.7806 0.044(6) Uiso calc R 1 H
C7 0.07724(18) 0.1412(2) 0.85555(17) 0.0380(5) Uani d . 1 C
C8 -0.0371(2) 0.0692(3) 0.8092(2) 0.0493(6) Uani d . 1 C
H8 -0.0555 0.0081 0.7467 0.061(7) Uiso calc R 1 H
C9 -0.1237(2) 0.0876(3) 0.8552(2) 0.0554(7) Uani d . 1 C
H9 -0.1996 0.0385 0.8234 0.062(7) Uiso calc R 1 H
C10 -0.0986(2) 0.1769(3) 0.9467(2) 0.0563(7) Uani d . 1 C
H10 -0.1564 0.1871 0.9783 0.067(8) Uiso calc R 1 H
C11 0.0132(2) 0.2523(3) 0.9923(2) 0.0597(7) Uani d . 1 C
H11 0.0297 0.3154 1.0535 0.088(10) Uiso calc R 1 H
C12 0.1009(2) 0.2344(3) 0.94726(18) 0.0501(6) Uani d . 1 C
H12 0.1760 0.2851 0.9787 0.056(7) Uiso calc R 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
C1' 0.0415(12) 0.0378(12) 0.0454(13) 0.0042(11) 0.0204(11) 0.0025(10)
O1' 0.0611(10) 0.0483(10) 0.0734(11) 0.0186(8) 0.0414(9) 0.0117(8)
C2' 0.0403(12) 0.0350(12) 0.0443(12) 0.0036(10) 0.0197(10) 0.0041(10)
O2' 0.0639(11) 0.0466(10) 0.0788(12) 0.0152(9) 0.0453(10) 0.0238(9)
C3' 0.0365(11) 0.0357(12) 0.0422(12) 0.0031(10) 0.0166(10) -0.0016(10)
O3' 0.0610(10) 0.0392(9) 0.0697(11) 0.0154(8) 0.0416(9) 0.0094(8)
C4' 0.0397(12) 0.0316(11) 0.0379(12) 0.0024(10) 0.0159(10) 0.0024(10)
O4' 0.0588(10) 0.0360(8) 0.0645(10) 0.0066(8) 0.0364(8) 0.0113(8)
N1 0.0480(11) 0.0412(11) 0.0503(11) -0.0004(9) 0.0280(9) 0.0000(9)
C2 0.0575(14) 0.0348(13) 0.0564(14) -0.0057(11) 0.0304(12) -0.0076(11)
C3 0.0469(13) 0.0379(12) 0.0519(14) -0.0094(11) 0.0241(11) -0.0038(11)
C4 0.0380(12) 0.0364(12) 0.0333(11) 0.0005(10) 0.0113(9) 0.0029(9)
C5 0.0430(12) 0.0339(12) 0.0454(13) -0.0029(10) 0.0184(10) -0.0028(10)
C6 0.0473(13) 0.0368(13) 0.0509(14) -0.0071(11) 0.0244(11) -0.0008(11)
C7 0.0377(12) 0.0362(12) 0.0406(12) 0.0010(10) 0.0164(10) 0.0045(10)
C8 0.0443(13) 0.0436(14) 0.0599(15) -0.0030(11) 0.0209(11) -0.0042(12)
C9 0.0416(14) 0.0506(15) 0.0770(18) -0.0004(12) 0.0272(13) 0.0040(14)
C10 0.0538(15) 0.0595(16) 0.0675(17) 0.0154(13) 0.0369(14) 0.0182(14)
C11 0.0647(17) 0.0702(18) 0.0537(15) 0.0046(15) 0.0338(13) -0.0051(14)
C12 0.0453(14) 0.0590(15) 0.0480(13) -0.0043(12) 0.0210(11) -0.0078(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1' O1' 1.217(2) no
C1' C2' 1.485(3) no
C1' C4' 1.497(3) no
C2' O2' 1.252(2) no
C2' C3' 1.424(3) no
C3' O3' 1.310(2) no
C3' C4' 1.420(3) no
O3' H3' 1.01(4) no
C4' O4' 1.242(2) no
N1 C2 1.329(3) no
N1 C6 1.332(3) no
N1 H1 0.8600 no
C2 C3 1.366(3) no
C2 H2 0.9300 no
C3 C4 1.400(3) no
C3 H3 0.9300 no
C4 C5 1.391(3) no
C4 C7 1.482(3) no
C5 C6 1.369(3) no
C5 H5 0.9300 no
C6 H6 0.9300 no
C7 C12 1.389(3) no
C7 C8 1.393(4) no
C8 C9 1.385(4) no
C8 H8 0.9300 no
C9 C10 1.365(3) no
C9 H9 0.9300 no
C10 C11 1.383(4) no
C10 H10 0.9300 no
C11 C12 1.388(4) no
C11 H11 0.9300 no
C12 H12 0.9300 no
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
O1' C1' C2' 135.8(2) no
O1' C1' C4' 136.4(2) no
C2' C1' C4' 87.80(16) no
O2' C2' C3' 137.6(2) no
O2' C2' C1' 132.8(2) no
C3' C2' C1' 89.62(16) no
O3' C3' C4' 129.1(2) no
O3' C3' C2' 137.7(2) no
C4' C3' C2' 93.26(17) no
C3' O3' H3' 114.5(19) no
O4' C4' C3' 134.8(2) no
O4' C4' C1' 135.84(19) no
C3' C4' C1' 89.32(16) no
C2 N1 C6 121.4(2) no
C2 N1 H1 119.3 no
C6 N1 H1 119.3 no
N1 C2 C3 120.7(2) no
N1 C2 H2 119.6 no
C3 C2 H2 119.6 no
C2 C3 C4 120.3(2) no
C2 C3 H3 119.9 no
C4 C3 H3 119.9 no
C5 C4 C3 116.7(2) no
C5 C4 C7 121.7(2) no
C3 C4 C7 121.7(2) no
C6 C5 C4 120.8(2) no
C6 C5 H5 119.6 no
C4 C5 H5 119.6 no
N1 C6 C5 120.2(2) no
N1 C6 H6 119.9 no
C5 C6 H6 119.9 no
C12 C7 C8 118.3(3) no
C12 C7 C4 120.4(2) no
C8 C7 C4 121.3(2) no
C9 C8 C7 120.7(2) no
C9 C8 H8 119.7 no
C7 C8 H8 119.7 no
C10 C9 C8 120.6(3) no
C10 C9 H9 119.7 no
C8 C9 H9 119.7 no
C9 C10 C11 119.6(3) no
C9 C10 H10 120.2 no
C11 C10 H10 120.2 no
C10 C11 C12 120.3(2) no
C10 C11 H11 119.8 no
C12 C11 H11 119.8 no
C11 C12 C7 120.4(3) no
C11 C12 H12 119.8 no
C7 C12 H12 119.8 no
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
O3' H3' O2' 3_666 1.01(4) 1.52(4) 2.493(2) 161(3) y
N1 H1 O4' . 0.86 1.84 2.697(3) 171 y