#------------------------------------------------------------------------------
#$Date: 2016-03-26 19:32:58 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180439 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/08/7210895.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_7210895
loop_
_publ_author_name
'Ford, Samantha J.'
'McIntyre, Garry J.'
'Johnson, Mark R.'
'Evans, Ivana Radosavljević'
_publ_section_title
;
 Structure and dynamics studies of the short strong hydrogen bond in the
 3,5-dinitrobenzoic acid--nicotinic acid molecular complex
;
_journal_issue                   37
_journal_name_full               CrystEngComm
_journal_page_first              7576
_journal_paper_doi               10.1039/c3ce40874d
_journal_volume                  15
_journal_year                    2013
_chemical_formula_sum            'C13 H9 N3 O8'
_chemical_formula_weight         335.00
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 102.641(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.061(6)
_cell_length_b                   5.039(2)
_cell_length_c                   19.598(8)
_cell_measurement_temperature    30
_cell_volume                     1354.9(10)
_computing_cell_refinement       LAUEGEN
_computing_data_collection       VIVALDI
_computing_data_reduction        'INTEGRATE+, LAUE4'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      30.0(2)
_diffrn_detector_area_resol_mean 0.072
_diffrn_measured_fraction_theta_full 0.730
_diffrn_measured_fraction_theta_max 0.730
_diffrn_measurement_device_type  'VIVALDI cylindrical image-plate detector'
_diffrn_measurement_method       Laue
_diffrn_radiation_monochromator  N/A
_diffrn_radiation_probe          neutron
_diffrn_radiation_source         'ILL HFR'
_diffrn_radiation_type           'thermal neutrons'
_diffrn_radiation_wavelength     'thermal neutron spectrum'
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            13847
_diffrn_reflns_theta_full        30.51
_diffrn_reflns_theta_max         72.0
_diffrn_reflns_theta_min         1.8
_exptl_absorpt_coefficient_mu    0.000
_exptl_crystal_density_diffrn    1.642
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             509
_exptl_crystal_size_max          1.1
_exptl_crystal_size_mid          0.8
_exptl_crystal_size_min          0.5
_refine_diff_density_max         1.289
_refine_diff_density_min         -1.342
_refine_diff_density_rms         0.312
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         3018
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.1958
_refine_ls_R_factor_gt           0.0877
_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/[σ²(Fo²)+(0.0300P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1417
_refine_ls_wR_factor_ref         0.1666
_reflns_number_gt                1516
_reflns_number_total             3018
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ce40874d.txt
_cod_data_source_block           35dbna_30c
_cod_depositor_comments
;
The following automatic conversions were performed:

'_diffrn_ambient_temperature' value '30(.2)' was changed to '30.0(2)'
- precision was estimated.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               7210895
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
O1 O 0.4122(3) -0.0708(8) 0.35616(19) 0.0154(8) Uani 1 1 d
O2 O 0.4783(3) 0.2521(7) 0.4334(2) 0.0155(9) Uani 1 1 d
N1 N 0.21811(18) 0.6370(5) 0.40969(12) 0.0147(5) Uani 1 1 d
C1 C 0.4052(2) 0.1358(7) 0.38704(16) 0.0127(7) Uani 1 1 d
C2 C 0.3126(3) 0.2907(7) 0.37570(17) 0.0131(7) Uani 1 1 d
C3 C 0.2335(3) 0.2219(7) 0.32228(17) 0.0154(7) Uani 1 1 d
H1 H 0.2387(6) 0.0543(15) 0.2886(4) 0.0291(16) Uani 1 1 d
C4 C 0.1467(3) 0.3655(7) 0.31262(16) 0.0143(7) Uani 1 1 d
H2 H 0.0836(6) 0.3185(17) 0.2703(4) 0.0311(17) Uani 1 1 d
C5 C 0.1403(2) 0.5726(7) 0.35886(16) 0.0140(6) Uani 1 1 d
H3 H 0.0753(6) 0.6921(17) 0.3549(4) 0.0297(16) Uani 1 1 d
C6 C 0.3034(3) 0.5051(6) 0.41901(17) 0.0125(7) Uani 1 1 d
H4 H 0.3603(6) 0.5755(15) 0.4616(4) 0.0296(16) Uani 1 1 d
H9 H 0.5376(6) 0.1336(16) 0.4414(4) 0.0300(16) Uani 1 1 d
H8 H 0.2084(5) 0.8047(17) 0.4469(4) 0.0278(15) Uani 1 1 d
O3 O 0.3541(3) -0.0241(8) 0.5326(2) 0.0154(8) Uani 1 1 d
O4 O 0.1941(3) 0.0125(7) 0.4938(2) 0.0142(8) Uani 1 1 d
O5 O 0.5087(3) 0.6036(8) 0.7239(2) 0.0168(8) Uani 1 1 d
O6 O 0.4226(3) 0.9306(8) 0.7501(2) 0.0166(8) Uani 1 1 d
O7 O 0.0784(3) 0.9809(8) 0.6534(2) 0.0185(9) Uani 1 1 d
O8 O 0.0088(3) 0.6907(9) 0.5757(2) 0.0185(8) Uani 1 1 d
N2 N 0.0799(2) 0.7800(5) 0.61732(12) 0.0157(5) Uani 1 1 d
N3 N 0.4316(2) 0.7217(5) 0.71893(12) 0.0139(5) Uani 1 1 d
C7 C 0.2739(2) 0.0767(7) 0.53255(16) 0.0136(6) Uani 1 1 d
C8 C 0.2683(2) 0.3059(7) 0.58231(16) 0.0136(6) Uani 1 1 d
C9 C 0.1787(3) 0.4295(7) 0.57960(17) 0.0143(7) Uani 1 1 d
H5 H 0.1139(6) 0.3574(16) 0.5415(4) 0.0299(17) Uani 1 1 d
C10 C 0.1733(2) 0.6433(7) 0.62324(16) 0.0132(7) Uani 1 1 d
C11 C 0.2553(3) 0.7381(6) 0.67110(17) 0.0134(7) Uani 1 1 d
H6 H 0.2502(6) 0.9054(16) 0.7039(4) 0.0309(17) Uani 1 1 d
C12 C 0.3436(2) 0.6129(7) 0.67172(16) 0.0130(7) Uani 1 1 d
C13 C 0.3531(3) 0.3980(7) 0.62841(16) 0.0151(7) Uani 1 1 d
H7 H 0.4256(6) 0.3070(17) 0.6294(4) 0.0313(17) 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 0.0000 0.0000 '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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0000 0.0000 '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 O2 H9 109.3(5)
C6 N1 C5 122.4(3)
C6 N1 H8 120.3(4)
C5 N1 H8 117.3(4)
O1 C1 O2 125.0(4)
O1 C1 C2 122.4(3)
O2 C1 C2 112.6(3)
C3 C2 C6 118.9(3)
C3 C2 C1 120.6(3)
C6 C2 C1 120.5(3)
C2 C3 C4 120.2(3)
C2 C3 H1 120.1(5)
C4 C3 H1 119.7(5)
C3 C4 C5 118.5(3)
C3 C4 H2 121.9(5)
C5 C4 H2 119.6(5)
N1 C5 C4 120.1(3)
N1 C5 H3 117.0(5)
C4 C5 H3 122.8(5)
N1 C6 C2 119.8(3)
N1 C6 H4 115.4(5)
C2 C6 H4 124.8(5)
O8 N2 O7 124.4(4)
O8 N2 C10 117.7(3)
O7 N2 C10 117.8(3)
O5 N3 O6 124.1(4)
O5 N3 C12 118.4(3)
O6 N3 C12 117.5(3)
O3 C7 O4 126.2(4)
O3 C7 C8 119.0(3)
O4 C7 C8 114.8(3)
C9 C8 C13 120.5(3)
C9 C8 C7 119.0(3)
C13 C8 C7 120.4(3)
C10 C9 C8 119.5(3)
C10 C9 H5 121.6(5)
C8 C9 H5 118.8(5)
C9 C10 C11 122.0(3)
C9 C10 N2 119.0(3)
C11 C10 N2 119.0(3)
C12 C11 C10 117.0(3)
C12 C11 H6 121.9(6)
C10 C11 H6 121.1(5)
C11 C12 C13 123.3(3)
C11 C12 N3 117.4(3)
C13 C12 N3 119.2(3)
C12 C13 C8 117.7(3)
C12 C13 H7 121.1(5)
C8 C13 H7 121.2(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.219(5)
O2 C1 1.348(5)
O2 H9 1.010(10)
N1 C6 1.348(4)
N1 C5 1.348(4)
N1 H8 1.144(8)
C1 C2 1.492(5)
C2 C3 1.395(5)
C2 C6 1.397(5)
C3 C4 1.395(5)
C3 H1 1.085(8)
C4 C5 1.398(5)
C4 H2 1.099(8)
C5 H3 1.083(8)
C6 H4 1.082(7)
O3 C7 1.238(5)
O4 C7 1.251(6)
O5 N3 1.221(5)
O6 N3 1.237(4)
O7 N2 1.238(5)
O8 N2 1.228(5)
N2 C10 1.466(4)
N3 C12 1.480(4)
C7 C8 1.524(5)
C8 C9 1.397(5)
C8 C13 1.407(5)
C9 C10 1.388(5)
C9 H5 1.105(8)
C10 C11 1.402(5)
C11 C12 1.389(5)
C11 H6 1.072(8)
C12 C13 1.400(5)
C13 H7 1.115(9)
