#------------------------------------------------------------------------------
#$Date: 2016-03-24 01:48:54 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179541 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/10/4501058.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_4501058
loop_
_publ_author_name
'Stilinović, Vladimir'
'Kaitner, Branko'
_publ_section_title
;
 Hydrogen Bonding in Pyridinium Picrates: From Discrete Ion Pairs to 3D
 Networks
;
_journal_issue                   9
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              4110
_journal_paper_doi               10.1021/cg200684x
_journal_volume                  11
_journal_year                    2011
_chemical_formula_moiety         'C6 H2 N3 O7, C6 H8 N'
_chemical_formula_sum            'C12 H10 N4 O7'
_chemical_formula_weight         322.24
_chemical_name_systematic
;
3-methylpyridinium picrate
;
_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_date             2010-09-20T10:18:54-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 101.897(18)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.2280(12)
_cell_length_b                   13.663(2)
_cell_length_c                   11.852(3)
_cell_measurement_reflns_used    924
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      32.0
_cell_measurement_theta_min      4.6
_cell_volume                     1303.8(4)
_computing_cell_refinement
;
CrysAlis RED 170 (Oxford Diffraction Poland Sp., 2003)
;
_computing_data_collection
;
CrysAlis CCD 170 (Oxford Diffraction Poland Sp., 2003)
;
_computing_data_reduction
;
CrysAlis RED 170 (Oxford Diffraction Poland Sp., 2003)
;
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material
;
WinGX (Farrugia, 1999) 
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.941
_diffrn_measured_fraction_theta_max 0.941
_diffrn_measurement_device_type
;
Oxford Diffraction Xcalibur CCD
diffractometer
;
_diffrn_measurement_method       'omega scan'
_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  0.042
_diffrn_reflns_av_unetI/netI     0.0949
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5291
_diffrn_reflns_theta_full        27
_diffrn_reflns_theta_max         27
_diffrn_reflns_theta_min         3.91
_exptl_absorpt_coefficient_mu    0.138
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.642
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.531
_exptl_crystal_size_mid          0.087
_exptl_crystal_size_min          0.051
_refine_diff_density_max         0.337
_refine_diff_density_min         -0.399
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.897
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         2683
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.915
_refine_ls_R_factor_all          0.1582
_refine_ls_R_factor_gt           0.0646
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0948P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1579
_refine_ls_wR_factor_ref         0.186
_reflns_number_gt                1121
_reflns_number_total             2683
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg200684x_si_002.cif
_cod_data_source_block           3_mepy
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4501058
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_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
H4 H 0.739(5) 0.039(3) 0.082(4) 0.073(13) Uiso 1 1 d .
C4 C 0.9667(4) 0.1377(2) 0.6827(3) 0.0368(9) Uani 1 1 d .
C5 C 1.0039(4) 0.1836(2) 0.7880(3) 0.0393(9) Uani 1 1 d .
H5 H 1.0641 0.2416 0.7966 0.047 Uiso 1 1 calc R
C2 C 0.8267(4) 0.0099(2) 0.7598(4) 0.0402(9) Uani 1 1 d .
C3 C 0.8798(4) 0.0491(3) 0.6690(3) 0.0420(9) Uani 1 1 d .
H3 H 0.8586 0.0174 0.598 0.05 Uiso 1 1 calc R
C6 C 0.9516(4) 0.1432(3) 0.8806(3) 0.0394(9) Uani 1 1 d .
C1 C 0.8524(4) 0.0542(3) 0.8726(3) 0.0453(10) Uani 1 1 d .
N2 N 1.0163(4) 0.1810(3) 0.5835(3) 0.0526(9) Uani 1 1 d .
O1 O 0.7943(4) 0.0177(2) 0.9520(3) 0.0796(10) Uani 1 1 d .
N3 N 0.9969(4) 0.1947(3) 0.9888(3) 0.0596(10) Uani 1 1 d .
O5 O 1.0896(4) 0.2599(2) 0.5959(3) 0.0765(10) Uani 1 1 d .
O4 O 0.9813(4) 0.1383(2) 0.4895(3) 0.0799(10) Uani 1 1 d .
N1 N 0.7366(4) -0.0845(2) 0.7360(4) 0.0608(10) Uani 1 1 d .
O6 O 1.1041(4) 0.2582(2) 0.9987(3) 0.0789(10) Uani 1 1 d .
O3 O 0.6988(5) -0.1125(3) 0.6359(4) 0.1058(14) Uani 1 1 d .
O7 O 0.9315(4) 0.1730(3) 1.0693(3) 0.0954(12) Uani 1 1 d .
O2 O 0.6933(5) -0.1256(3) 0.8129(4) 0.1269(17) Uani 1 1 d .
N4 N 0.7036(4) 0.0102(3) 0.1505(3) 0.0514(9) Uani 1 1 d .
C8 C 0.5606(4) -0.1195(3) 0.2191(3) 0.0481(10) Uani 1 1 d DU
C10 C 0.6698(5) 0.0159(3) 0.3383(4) 0.0526(11) Uani 1 1 d .
H10 H 0.6847 0.0482 0.4087 0.063 Uiso 1 1 calc R
C9 C 0.5886(5) -0.0715(3) 0.3247(3) 0.0503(10) Uani 1 1 d .
H9 H 0.5515 -0.0992 0.3865 0.06 Uiso 1 1 calc R
C7 C 0.6221(5) -0.0751(3) 0.1300(3) 0.0511(11) Uani 1 1 d .
H7 H 0.6066 -0.1043 0.0577 0.061 Uiso 1 1 calc R
C11 C 0.7295(5) 0.0567(3) 0.2503(4) 0.0551(11) Uani 1 1 d .
H11 H 0.7869 0.1158 0.2601 0.066 Uiso 1 1 calc R
C12 C 0.4747(4) -0.2083(2) 0.2013(3) 0.0449(10) Uani 1 1 d DU
H12A H 0.4207 -0.2138 0.1216 0.067 Uiso 1 1 calc R
H12B H 0.3929 -0.2105 0.2485 0.067 Uiso 1 1 calc R
H12C H 0.5513 -0.2615 0.2216 0.067 Uiso 1 1 calc R
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 0 '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 0.006 '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
C5 C4 C3 120.9(3)
C5 C4 N2 120.3(3)
C3 C4 N2 118.8(3)
C4 C5 C6 119.6(3)
C4 C5 H5 120.2
C6 C5 H5 120.2
C3 C2 C1 124.1(3)
C3 C2 N1 115.0(4)
C1 C2 N1 120.8(3)
C2 C3 C4 119.4(4)
C2 C3 H3 120.3
C4 C3 H3 120.3
C5 C6 N3 116.6(4)
C5 C6 C1 123.1(4)
N3 C6 C1 120.3(3)
O1 C1 C2 121.8(4)
O1 C1 C6 125.6(4)
C2 C1 C6 112.6(3)
O5 N2 O4 122.6(4)
O5 N2 C4 118.4(4)
O4 N2 C4 119.1(3)
O7 N3 O6 121.2(4)
O7 N3 C6 120.0(4)
O6 N3 C6 118.7(4)
O2 N1 O3 122.8(4)
O2 N1 C2 118.8(4)
O3 N1 C2 118.1(4)
C11 N4 C7 124.2(4)
C11 N4 H4 121(2)
C7 N4 H4 114(2)
C12 C8 C9 122.0(4)
C12 C8 C7 120.9(4)
C9 C8 C7 117.1(4)
C11 C10 C9 121.0(4)
C11 C10 H10 119.5
C9 C10 H10 119.5
C10 C9 C8 120.5(4)
C10 C9 H9 119.8
C8 C9 H9 119.8
N4 C7 C8 119.1(4)
N4 C7 H7 120.5
C8 C7 H7 120.5
N4 C11 C10 118.2(4)
N4 C11 H11 120.9
C10 C11 H11 120.9
C8 C12 H12A 109.5
C8 C12 H12B 109.5
H12A C12 H12B 109.5
C8 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C4 C5 1.374(5)
C4 C3 1.398(5)
C4 N2 1.448(4)
C5 C6 1.374(5)
C5 H5 0.93
C2 C3 1.354(5)
C2 C1 1.443(5)
C2 N1 1.486(5)
C3 H3 0.93
C6 N3 1.442(5)
C6 C1 1.456(5)
C1 O1 1.244(4)
N2 O5 1.229(4)
N2 O4 1.238(4)
N3 O7 1.225(4)
N3 O6 1.226(4)
N1 O2 1.185(5)
N1 O3 1.224(5)
N4 C11 1.321(5)
N4 C7 1.342(5)
N4 H4 1.00(4)
C8 C12 1.398(4)
C8 C9 1.389(5)
C8 C7 1.400(5)
C10 C11 1.360(6)
C10 C9 1.362(5)
C10 H10 0.93
C9 H9 0.93
C7 H7 0.93
C11 H11 0.93
C12 H12A 0.96
C12 H12B 0.96
C12 H12C 0.96
