#------------------------------------------------------------------------------
#$Date: 2016-03-24 01:48:54 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179541 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/10/4501067.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_4501067
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, C5 H9 N2'
_chemical_formula_sum            'C12 H11 N5 O7'
_chemical_formula_weight         337.26
_chemical_name_systematic
;
2-pyridylmethylammonium picrate
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2010-10-12T17:39:57-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 142.052(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   35.020(4)
_cell_length_b                   4.6148(3)
_cell_length_c                   29.095(2)
_cell_measurement_reflns_used    1294
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      32.0
_cell_measurement_theta_min      4.6
_cell_volume                     2891.5(5)
_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 0.983
_diffrn_measured_fraction_theta_max 0.983
_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  0.0188
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_limit_h_max       41
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            7433
_diffrn_reflns_theta_full        25.49
_diffrn_reflns_theta_max         25.49
_diffrn_reflns_theta_min         3.95
_exptl_absorpt_coefficient_mu    0.13
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.549
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.573
_exptl_crystal_size_mid          0.471
_exptl_crystal_size_min          0.324
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.437
_refine_diff_density_rms         0.05
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         2651
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0632
_refine_ls_R_factor_gt           0.0463
_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)+(0.0928P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1329
_refine_ls_wR_factor_ref         0.1393
_reflns_number_gt                1886
_reflns_number_total             2651
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg200684x_si_002.cif
_cod_data_source_block           2-meampy
_cod_original_cell_volume        2891.5(4)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4501067
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_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
O1 O 0.07781(6) 0.6974(3) 0.93499(7) 0.0391(4) Uani 1 1 d .
C6 C 0.07494(8) 0.7239(4) 1.01359(11) 0.0354(4) Uani 1 1 d .
C1 C 0.10133(8) 0.6318(4) 0.99579(10) 0.0331(4) Uani 1 1 d .
N3 N 0.01780(8) 0.8904(4) 0.95710(9) 0.0412(4) Uani 1 1 d .
C2 C 0.15447(8) 0.4478(4) 1.05319(10) 0.0384(5) Uani 1 1 d .
C4 C 0.14820(9) 0.4775(5) 1.12845(11) 0.0452(5) Uani 1 1 d .
C3 C 0.17684(9) 0.3737(4) 1.11694(11) 0.0448(5) Uani 1 1 d .
H3 H 0.2113 0.2534 1.1522 0.054 Uiso 1 1 calc R
C5 C 0.09636(10) 0.6513(4) 1.07626(12) 0.0430(5) Uani 1 1 d .
H5 H 0.0765 0.7174 1.0838 0.052 Uiso 1 1 calc R
N1 N 0.18621(8) 0.3219(4) 1.04389(11) 0.0516(5) Uani 1 1 d .
O7 O 0.01540(8) 1.1032(4) 0.93045(10) 0.0617(5) Uani 1 1 d .
O6 O -0.02561(8) 0.8121(4) 0.93945(11) 0.0738(6) Uani 1 1 d .
N2 N 0.17156(10) 0.4014(5) 1.19601(12) 0.0637(6) Uani 1 1 d .
O5 O 0.15101(11) 0.5290(5) 1.20955(11) 0.0936(7) Uani 1 1 d .
O2 O 0.16772(10) 0.3569(5) 0.98819(12) 0.0965(8) Uani 1 1 d .
O4 O 0.21039(10) 0.2118(5) 1.23540(12) 0.0991(7) Uani 1 1 d .
O3 O 0.22971(13) 0.1730(7) 1.09201(16) 0.1438(13) Uani 1 1 d .
H5B H 0.0414(9) 0.156(4) 0.8289(13) 0.042(6) Uiso 1 1 d .
H5C H 0.0599(10) 0.354(5) 0.8836(13) 0.046(6) Uiso 1 1 d .
H5A H 0.0379(10) 0.059(5) 0.8734(13) 0.044(6) Uiso 1 1 d .
N5 N 0.03141(8) 0.2060(4) 0.84886(10) 0.0370(4) Uani 1 1 d .
N4 N -0.08410(8) 0.0178(4) 0.68648(9) 0.0431(4) Uani 1 1 d .
C12 C -0.03271(9) 0.3177(4) 0.79162(11) 0.0431(5) Uani 1 1 d .
H12A H -0.0373 0.4826 0.7669 0.052 Uiso 1 1 calc R
H12B H -0.0398 0.3848 0.816 0.052 Uiso 1 1 calc R
C7 C -0.08077(9) 0.0952(4) 0.73409(11) 0.0386(5) Uani 1 1 d .
C11 C -0.12807(10) -0.1697(5) 0.63251(12) 0.0497(6) Uani 1 1 d .
H11 H -0.1311 -0.2226 0.5988 0.06 Uiso 1 1 calc R
C8 C -0.12010(10) -0.0171(5) 0.72938(13) 0.0517(6) Uani 1 1 d .
H8 H -0.1165 0.0385 0.7634 0.062 Uiso 1 1 calc R
C9 C -0.16485(11) -0.2123(6) 0.67377(15) 0.0609(6) Uani 1 1 d .
H9 H -0.1918 -0.2913 0.6698 0.073 Uiso 1 1 calc R
C10 C -0.16930(11) -0.2889(5) 0.62442(14) 0.0575(6) Uani 1 1 d .
H10 H -0.1995 -0.4191 0.586 0.069 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 C6 C1 125.51(18)
C5 C6 N3 117.36(17)
C1 C6 N3 116.94(16)
O1 C1 C6 122.63(17)
O1 C1 C2 125.74(17)
C6 C1 C2 111.55(17)
O7 N3 O6 122.57(18)
O7 N3 C6 119.42(17)
O6 N3 C6 117.99(17)
C3 C2 C1 123.62(18)
C3 C2 N1 116.51(18)
C1 C2 N1 119.84(17)
C3 C4 C5 121.10(18)
C3 C4 N2 120.3(2)
C5 C4 N2 118.6(2)
C4 C3 C2 119.74(19)
C4 C3 H3 120.1
C2 C3 H3 120.1
C6 C5 C4 118.5(4)
C6 C5 H5 120.8
C4 C5 H5 120.8
O3 N1 O2 120.2(2)
O3 N1 C2 118.2(2)
O2 N1 C2 121.55(18)
O5 N2 O4 123.7(2)
O5 N2 C4 118.4(2)
O4 N2 C4 117.9(2)
C12 N5 H5B 112.0(14)
C12 N5 H5C 109.9(13)
H5B N5 H5C 104.4(18)
C12 N5 H5A 112(3)
H5B N5 H5A 109.9(19)
H5C N5 H5A 108(2)
C11 N4 C7 117.92(17)
N5 C12 C7 112.95(16)
N5 C12 H12A 109
C7 C12 H12A 109
N5 C12 H12B 109
C7 C12 H12B 109
H12A C12 H12B 107.8
N4 C7 C8 122.14(19)
N4 C7 C12 116.21(17)
C8 C7 C12 121.63(19)
N4 C11 C10 122.8(2)
N4 C11 H11 118.6
C10 C11 H11 118.6
C9 C8 C7 119.2(2)
C9 C8 H8 120.4
C7 C8 H8 120.4
C10 C9 C8 119.2(2)
C10 C9 H9 120.4
C8 C9 H9 120.4
C9 C10 C11 118.8(2)
C9 C10 H10 120.6
C11 C10 H10 120.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.265(2)
C6 C5 1.357(3)
C6 C1 1.435(3)
C6 N3 1.452(2)
C1 C2 1.439(3)
N3 O7 1.213(2)
N3 O6 1.214(5)
C2 C3 1.371(3)
C2 N1 1.456(3)
C4 C3 1.370(3)
C4 C5 1.377(3)
C4 N2 1.456(3)
C3 H3 0.93
C5 H5 0.93
N1 O3 1.179(3)
N1 O2 1.190(3)
N2 O5 1.211(3)
N2 O4 1.213(3)
N5 C12 1.478(3)
N5 H5B 0.91(2)
N5 H5C 0.94(2)
N5 H5A 0.88(2)
N4 C11 1.331(3)
N4 C7 1.344(3)
C12 C7 1.498(3)
C12 H12A 0.97
C12 H12B 0.97
C7 C8 1.374(3)
C11 C10 1.381(3)
C11 H11 0.93
C8 C9 1.374(3)
C8 H8 0.93
C9 C10 1.363(4)
C9 H9 0.93
C10 H10 0.93
