#------------------------------------------------------------------------------
#$Date: 2017-06-06 09:20:00 +0300 (Tue, 06 Jun 2017) $
#$Revision: 197562 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/62/1546264.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_1546264
loop_
_publ_author_name
'Rajput, Lalit'
'Banik, Manas'
'Yarava, Jayasubba Reddy'
'Joseph, Sumy'
'Pandey, Manoj Kumar'
'Nishiyama, Yusuke'
'Desiraju, Gautam R.'
_publ_section_title
;
 Exploring the salt--cocrystal continuum with solid-state NMR using
 natural-abundance samples: implications for crystal engineering
;
_journal_issue                   4
_journal_name_full               IUCrJ
_journal_page_first
;
;
_journal_paper_doi               10.1107/S205225251700687X
_journal_volume                  4
_journal_year                    2017
_chemical_formula_moiety         'C7 H3 N2 O6, C7 H10 N'
_chemical_formula_sum            'C14 H13 N3 O6'
_chemical_formula_weight         319.27
_chemical_melting_point          120.5(15)
_chemical_name_common            '4-Ethylpyridinium 3,5-Dinitrobenzoate'
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 94.440(13)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.574(9)
_cell_length_b                   14.346(15)
_cell_length_c                   12.190(13)
_cell_measurement_reflns_used    5147
_cell_measurement_temperature    298
_cell_measurement_theta_max      33.6
_cell_measurement_theta_min      1.7
_cell_volume                     1495(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  Rigaku
_diffrn_measurement_method       'profile data from ω-scans'
_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  0.0804
_diffrn_reflns_av_sigmaI/netI    0.0452
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13680
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.20
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.833
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.135
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         2936
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.135
_refine_ls_R_factor_all          0.0626
_refine_ls_R_factor_gt           0.0555
_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)+(0.0968P)²+0.2206P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1606
_refine_ls_wR_factor_ref         0.1737
_reflns_number_gt                2597
_reflns_number_total             2936
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            lq5005.cif
_cod_data_source_block           SA-2-RT
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '119-122' was changed to '120.5(15)'
- the average value was taken and precision was estimated.

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/IUCr/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               1546264
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_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
H1N H -0.041(4) 0.255(2) 0.970(3) 0.115(10) Uiso 1 1 d .
H8 H 0.628(2) 0.3388(15) 0.7471(17) 0.055(5) Uiso 1 1 d .
H10 H 0.538(3) 0.1206(18) 0.940(2) 0.076(7) Uiso 1 1 d .
H12 H 0.802(3) 0.0834(17) 0.676(2) 0.066(6) Uiso 1 1 d .
H1 H 0.029(3) 0.0985(18) 0.984(2) 0.077(7) Uiso 1 1 d .
H2 H 0.172(3) 0.009(2) 0.864(2) 0.080(7) Uiso 1 1 d .
H4 H 0.207(3) 0.2468(17) 0.681(2) 0.073(6) Uiso 1 1 d .
H5 H 0.063(2) 0.3231(16) 0.8120(18) 0.058(5) Uiso 1 1 d .
H6A H 0.361(3) 0.1042(19) 0.638(2) 0.085(8) Uiso 1 1 d .
H6B H 0.356(3) 0.0135(19) 0.709(2) 0.078(7) Uiso 1 1 d .
N1 N 0.03790(17) 0.21530(10) 0.90713(12) 0.0497(4) Uani 1 1 d .
C1 C 0.0693(2) 0.12469(14) 0.92256(16) 0.0562(5) Uani 1 1 d .
C2 C 0.1527(2) 0.07456(13) 0.85079(16) 0.0554(5) Uani 1 1 d .
C3 C 0.20643(18) 0.11811(12) 0.75876(14) 0.0461(4) Uani 1 1 d .
C4 C 0.1747(2) 0.21284(12) 0.74503(15) 0.0496(4) Uani 1 1 d .
C5 C 0.0903(2) 0.25934(13) 0.81997(15) 0.0518(4) Uani 1 1 d .
C6 C 0.2904(2) 0.06335(15) 0.67594(17) 0.0576(5) Uani 1 1 d .
C7 C 0.1775(3) 0.0194(2) 0.5909(3) 0.1049(11) Uani 1 1 d .
H7A H 0.2344 -0.0149 0.5394 0.157 Uiso 1 1 calc R
H7B H 0.1165 0.0671 0.5526 0.157 Uiso 1 1 calc R
H7C H 0.1092 -0.0221 0.6262 0.157 Uiso 1 1 calc R
C14 C 0.8082(2) 0.26141(12) 0.60483(14) 0.0470(4) Uani 1 1 d .
C13 C 0.72647(18) 0.21817(11) 0.69838(13) 0.0430(4) Uani 1 1 d .
C8 C 0.63933(19) 0.27516(12) 0.76338(14) 0.0473(4) Uani 1 1 d .
C9 C 0.57078(19) 0.23589(12) 0.85189(14) 0.0474(4) Uani 1 1 d .
C10 C 0.5843(2) 0.14256(13) 0.87867(14) 0.0482(4) Uani 1 1 d .
C11 C 0.67191(19) 0.08839(12) 0.81216(13) 0.0461(4) Uani 1 1 d .
C12 C 0.74321(19) 0.12379(12) 0.72273(13) 0.0443(4) Uani 1 1 d .
N2 N 0.4801(2) 0.29688(12) 0.92097(14) 0.0619(4) Uani 1 1 d .
N3 N 0.6909(2) -0.01154(12) 0.83896(14) 0.0617(4) Uani 1 1 d .
O1 O 0.86720(18) 0.20299(9) 0.54057(11) 0.0601(4) Uani 1 1 d .
O2 O 0.81357(18) 0.34689(9) 0.59709(12) 0.0670(4) Uani 1 1 d .
O3 O 0.4634(2) 0.37841(12) 0.89479(18) 0.0948(6) Uani 1 1 d .
O4 O 0.4244(2) 0.26172(14) 1.00048(14) 0.0880(6) Uani 1 1 d .
O5 O 0.5973(3) -0.04787(12) 0.89583(17) 0.0982(7) Uani 1 1 d .
O6 O 0.7998(2) -0.05327(11) 0.80264(17) 0.0895(6) 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 0.0000 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_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 N1 C5 119.49(16)
N1 C1 C2 121.84(17)
C1 C2 C3 119.89(18)
C4 C3 C2 117.41(16)
C4 C3 C6 121.83(16)
C2 C3 C6 120.73(17)
C5 C4 C3 119.96(16)
N1 C5 C4 121.39(18)
C7 C6 C3 111.46(19)
O2 C14 O1 125.98(16)
O2 C14 C13 119.15(15)
O1 C14 C13 114.86(16)
C12 C13 C8 120.01(16)
C12 C13 C14 120.83(15)
C8 C13 C14 119.10(16)
C9 C8 C13 118.78(17)
C10 C9 C8 123.00(16)
C10 C9 N2 118.56(16)
C8 C9 N2 118.44(17)
C9 C10 C11 116.42(16)
C10 C11 C12 123.13(17)
C10 C11 N3 118.07(16)
C12 C11 N3 118.79(15)
C11 C12 C13 118.66(15)
O3 N2 O4 123.99(18)
O3 N2 C9 118.42(17)
O4 N2 C9 117.58(18)
O5 N3 O6 123.58(19)
O5 N3 C11 118.37(18)
O6 N3 C11 118.06(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.338(3)
N1 C5 1.343(2)
C1 C2 1.375(3)
C2 C3 1.393(3)
C3 C4 1.393(3)
C3 C6 1.506(3)
C4 C5 1.380(3)
C6 C7 1.502(3)
C14 O2 1.231(2)
C14 O1 1.278(2)
C14 C13 1.517(2)
C13 C12 1.391(3)
C13 C8 1.395(2)
C8 C9 1.388(3)
C9 C10 1.381(3)
C9 N2 1.477(2)
C10 C11 1.385(3)
C11 C12 1.387(3)
C11 N3 1.477(3)
N2 O3 1.218(3)
N2 O4 1.222(2)
N3 O5 1.218(2)
N3 O6 1.221(3)
