#------------------------------------------------------------------------------
#$Date: 2016-03-24 01:48:54 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179541 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/10/4501072.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_4501072
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 H7 N2 O'
_chemical_formula_sum            'C12 H9 N5 O8'
_chemical_formula_weight         351.24
_chemical_name_systematic
;
3-carbamoylpyridinium picrate
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2010-10-18T15:14:13-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.7574(3)
_cell_length_b                   14.4873(4)
_cell_length_c                   24.7349(7)
_cell_measurement_reflns_used    827
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      32.0
_cell_measurement_theta_min      4.6
_cell_volume                     2779.80(15)
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0268
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            18472
_diffrn_reflns_theta_full        26.99
_diffrn_reflns_theta_max         26.99
_diffrn_reflns_theta_min         3.87
_exptl_absorpt_coefficient_mu    0.144
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.679
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1440
_exptl_crystal_size_max          0.381
_exptl_crystal_size_mid          0.138
_exptl_crystal_size_min          0.098
_refine_diff_density_max         0.444
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3015
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0798
_refine_ls_R_factor_gt           0.0469
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0833P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1287
_refine_ls_wR_factor_ref         0.1397
_reflns_number_gt                1949
_reflns_number_total             3015
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg200684x_si_002.cif
_cod_data_source_block           3-niac
_cod_database_code               4501072
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'
'-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_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 0.785(3) 0.464(2) 0.0160(11) 0.071(8) Uiso 1 1 d .
H5A H 0.708(4) 0.107(2) 0.0999(12) 0.072(8) Uiso 1 1 d .
H5B H 0.744(3) 0.206(2) 0.1062(10) 0.065(8) Uiso 1 1 d .
O8 O 0.6550(2) 0.09144(10) 0.00567(6) 0.0552(5) Uani 1 1 d .
N4 N 0.7567(2) 0.41072(12) 0.00075(7) 0.0400(4) Uani 1 1 d .
C8 C 0.6987(2) 0.25251(12) 0.00455(7) 0.0323(4) Uani 1 1 d .
C7 C 0.7482(3) 0.33288(12) 0.02962(8) 0.0350(4) Uani 1 1 d .
H7 H 0.7756 0.3331 0.0662 0.042 Uiso 1 1 calc R
C12 C 0.6876(3) 0.16036(13) 0.03290(8) 0.0380(5) Uani 1 1 d .
C9 C 0.6577(3) 0.25532(13) -0.05003(8) 0.0407(5) Uani 1 1 d .
H9 H 0.6249 0.2016 -0.0679 0.049 Uiso 1 1 calc R
N5 N 0.7102(3) 0.15801(15) 0.08521(8) 0.0606(7) Uani 1 1 d .
C11 C 0.7174(3) 0.41512(15) -0.05132(8) 0.0484(6) Uani 1 1 d .
H11 H 0.7251 0.471 -0.0696 0.058 Uiso 1 1 calc R
C10 C 0.6658(3) 0.33779(15) -0.07794(8) 0.0506(6) Uani 1 1 d .
H10 H 0.6363 0.3404 -0.1144 0.061 Uiso 1 1 calc R
C2 C 0.8230(3) 0.27686(13) 0.24482(7) 0.0346(4) Uani 1 1 d .
C6 C 0.9538(3) 0.41318(13) 0.20743(8) 0.0352(5) Uani 1 1 d .
O1 O 0.8333(3) 0.29998(11) 0.14973(6) 0.0618(5) Uani 1 1 d .
C4 C 0.9450(3) 0.39053(15) 0.30235(8) 0.0387(5) Uani 1 1 d .
C5 C 0.9920(3) 0.44398(15) 0.25858(8) 0.0380(5) Uani 1 1 d .
H5 H 1.0486 0.4999 0.2636 0.046 Uiso 1 1 calc R
N1 N 0.7331(2) 0.18873(12) 0.24124(7) 0.0425(4) Uani 1 1 d .
C1 C 0.8673(3) 0.32700(14) 0.19595(8) 0.0368(5) Uani 1 1 d .
C3 C 0.8604(3) 0.30763(14) 0.29554(8) 0.0376(5) Uani 1 1 d .
H3 H 0.8289 0.2728 0.3255 0.045 Uiso 1 1 calc R
N3 N 1.0093(3) 0.47128(13) 0.16320(8) 0.0450(5) Uani 1 1 d .
N2 N 0.9827(2) 0.42215(14) 0.35662(7) 0.0487(5) Uani 1 1 d U
O3 O 0.6500(2) 0.16309(12) 0.28066(7) 0.0630(5) Uani 1 1 d .
O5 O 1.0618(3) 0.49438(13) 0.36210(7) 0.0718(6) Uani 1 1 d .
O4 O 0.9329(2) 0.37592(14) 0.39505(6) 0.0686(5) Uani 1 1 d U
O2 O 0.7416(3) 0.14349(13) 0.20058(7) 0.0856(7) Uani 1 1 d .
O7 O 0.9451(3) 0.46226(14) 0.11831(7) 0.0834(7) Uani 1 1 d .
O6 O 1.1160(3) 0.52997(16) 0.17152(8) 0.0899(7) Uani 1 1 d .
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
C11 N4 C7 123.27(19)
C11 N4 H4 115.2(17)
C7 N4 H4 121.5(17)
C7 C8 C9 118.57(17)
C7 C8 C12 123.73(17)
C9 C8 C12 117.69(17)
N4 C7 C8 119.18(18)
N4 C7 H7 120.4
C8 C7 H7 120.4
O8 C12 N5 123.3(2)
O8 C12 C8 118.34(17)
N5 C12 C8 118.38(18)
C10 C9 C8 120.10(19)
C10 C9 H9 120
C8 C9 H9 120
C12 N5 H5A 117(2)
C12 N5 H5B 126.1(17)
H5A N5 H5B 116(3)
N4 C11 C10 119.93(19)
N4 C11 H11 120
C10 C11 H11 120
C11 C10 C9 118.93(19)
C11 C10 H10 120.5
C9 C10 H10 120.5
C3 C2 C1 123.55(18)
C3 C2 N1 116.39(18)
C1 C2 N1 120.06(16)
C5 C6 C1 124.17(18)
C5 C6 N3 116.31(19)
C1 C6 N3 119.50(17)
C3 C4 C5 121.24(18)
C3 C4 N2 118.99(19)
C5 C4 N2 119.77(19)
C6 C5 C4 118.9(2)
C6 C5 H5 120.6
C4 C5 H5 120.6
O2 N1 O3 121.92(19)
O2 N1 C2 120.15(18)
O3 N1 C2 117.93(17)
O1 C1 C6 123.63(18)
O1 C1 C2 124.13(19)
C6 C1 C2 112.23(16)
C2 C3 C4 119.91(19)
C2 C3 H3 120
C4 C3 H3 120
O6 N3 O7 120.68(19)
O6 N3 C6 119.12(19)
O7 N3 C6 120.18(19)
O5 N2 O4 122.7(2)
O5 N2 C4 118.4(2)
O4 N2 C4 118.86(19)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O8 C12 1.231(2)
N4 C11 1.325(3)
N4 C7 1.336(2)
N4 H4 0.89(3)
C8 C7 1.374(3)
C8 C9 1.387(3)
C8 C12 1.510(3)
C7 H7 0.93
C12 N5 1.306(3)
C9 C10 1.381(3)
C9 H9 0.93
N5 H5A 0.82(3)
N5 H5B 0.90(3)
C11 C10 1.360(3)
C11 H11 0.93
C10 H10 0.93
C2 C3 1.363(3)
C2 C1 1.451(3)
C2 N1 1.458(3)
C6 C5 1.374(3)
C6 C1 1.445(3)
C6 N3 1.446(3)
O1 C1 1.237(2)
C4 C3 1.379(3)
C4 C5 1.380(3)
C4 N2 1.448(3)
C5 H5 0.93
N1 O2 1.202(2)
N1 O3 1.227(2)
C3 H3 0.93
N3 O6 1.204(3)
N3 O7 1.224(2)
N2 O5 1.221(2)
N2 O4 1.225(3)
