#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:08:23 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179653 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/06/4510613.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_4510613
loop_
_publ_author_name
'Jones, Andrew O. F.'
'Blagden, Nicholas'
'McIntyre, Garry J.'
'Parkin, Andrew'
'Seaton, Colin C.'
'Thomas, Lynne H.'
'Wilson, Chick C.'
_publ_section_title
;
 Tuning Proton Disorder in 3,5-Dinitrobenzoic Acid Dimers: the Effect of
 Local Environment
;
_journal_issue                   2
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              497
_journal_paper_doi               10.1021/cg300906j
_journal_volume                  13
_journal_year                    2013
_chemical_formula_sum            'C7 H4 N2 O6'
_chemical_formula_weight         212.12
_chemical_name_systematic
;
 3,5-dinitrobenzoic acid
;
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 95.634(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.0486(12)
_cell_length_b                   8.8884(9)
_cell_length_c                   9.5167(8)
_cell_measurement_reflns_used    5118
_cell_measurement_temperature    300
_cell_measurement_theta_max      55.07
_cell_measurement_theta_min      6.13
_cell_volume                     845.89(15)
_computing_cell_refinement       'CrystalClear 1.4.0 (Rigaku, 2008)'
_computing_data_collection       'CrystalClear 1.4.0 (Rigaku, 2008)'
_computing_data_reduction        'CrystalClear 1.4.0 (Rigaku, 2008)'
_computing_molecular_graphics    'Mercury (McRae, 2006)'
_computing_publication_material  'WINGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      300
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID IP Image Plate'
_diffrn_measurement_method       'Image Plate'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0480
_diffrn_reflns_av_sigmaI/netI    0.0329
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10833
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.07
_exptl_absorpt_coefficient_mu    0.150
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8678
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR, Rigaku 1995'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.666
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.975
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         1920
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.975
_refine_ls_R_factor_all          0.0893
_refine_ls_R_factor_gt           0.0516
_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)+(0.0582P)²+0.2575P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1115
_refine_ls_wR_factor_ref         0.1282
_reflns_number_gt                1248
_reflns_number_total             1920
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file
35-dnba_300K_p21c_X-ray_disordered_model_CIF.cif
_cod_data_source_block           35-dnba_300k_p21c
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               4510613
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
H3 H 0.110(2) -0.060(2) 0.602(2) 0.053(6) Uiso 1 1 d .
H2 H 0.280(2) -0.271(2) 0.290(2) 0.043(6) Uiso 1 1 d .
H1 H 0.392(2) 0.151(3) 0.397(2) 0.057(7) Uiso 1 1 d .
H41 H 0.065(4) -0.513(6) 0.402(4) 0.062(12) Uiso 0.64 1 d P
H42 H -0.003(8) -0.411(10) 0.578(8) 0.06(2) Uiso 0.36 1 d P
O3 O 0.15367(18) 0.19749(19) 0.68296(18) 0.0674(5) Uani 1 1 d .
O1 O 0.03268(18) -0.3259(2) 0.57232(17) 0.0614(5) Uani 1 1 d .
O6 O 0.54126(17) 0.0195(2) 0.2400(2) 0.0722(6) Uani 1 1 d .
O2 O 0.10796(18) -0.4308(2) 0.38165(18) 0.0623(5) Uani 1 1 d .
N2 N 0.44506(18) -0.0641(2) 0.2223(2) 0.0485(5) Uani 1 1 d .
O5 O 0.42459(17) -0.1517(2) 0.12402(18) 0.0668(5) Uani 1 1 d .
N1 N 0.2365(2) 0.1975(2) 0.5982(2) 0.0558(5) Uani 1 1 d .
C3 C 0.1807(2) -0.1859(2) 0.4457(2) 0.0405(5) Uani 1 1 d .
C4 C 0.2699(2) -0.1865(2) 0.3430(2) 0.0409(5) Uani 1 1 d .
O4 O 0.3116(3) 0.3013(2) 0.5834(3) 0.1103(9) Uani 1 1 d .
C7 C 0.1010(2) -0.3237(2) 0.4691(2) 0.0451(5) Uani 1 1 d .
C6 C 0.3394(2) 0.0669(2) 0.4100(2) 0.0427(5) Uani 1 1 d .
C2 C 0.1683(2) -0.0599(2) 0.5293(2) 0.0416(5) Uani 1 1 d .
C1 C 0.2476(2) 0.0638(2) 0.5083(2) 0.0417(5) Uani 1 1 d .
C5 C 0.34720(19) -0.0609(2) 0.3282(2) 0.0402(5) Uani 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O3 0.0829(12) 0.0574(11) 0.0663(11) -0.0140(9) 0.0285(10) -0.0036(9)
O1 0.0788(12) 0.0526(11) 0.0565(10) -0.0047(8) 0.0257(9) -0.0254(9)
O6 0.0534(10) 0.0845(13) 0.0817(13) -0.0058(10) 0.0213(9) -0.0241(10)
O2 0.0832(13) 0.0404(9) 0.0669(11) -0.0086(8) 0.0266(9) -0.0197(9)
N2 0.0468(10) 0.0461(11) 0.0542(11) 0.0043(9) 0.0124(9) 0.0002(9)
O5 0.0763(12) 0.0642(11) 0.0645(11) -0.0163(9) 0.0301(9) -0.0099(9)
N1 0.0712(13) 0.0441(12) 0.0543(11) -0.0084(9) 0.0166(10) -0.0113(10)
C3 0.0427(11) 0.0365(11) 0.0422(11) 0.0033(9) 0.0039(9) -0.0033(9)
C4 0.0459(11) 0.0338(11) 0.0431(11) -0.0003(9) 0.0047(9) 0.0002(9)
O4 0.154(2) 0.0703(14) 0.1187(18) -0.0486(13) 0.0760(16) -0.0629(15)
C7 0.0529(12) 0.0401(12) 0.0437(11) -0.0002(10) 0.0114(10) -0.0054(10)
C6 0.0442(12) 0.0390(12) 0.0449(12) 0.0035(10) 0.0038(9) -0.0088(10)
C2 0.0438(11) 0.0407(12) 0.0413(11) 0.0014(9) 0.0088(9) -0.0033(9)
C1 0.0499(12) 0.0355(11) 0.0398(11) -0.0017(9) 0.0055(9) -0.0028(9)
C5 0.0384(11) 0.0416(11) 0.0411(11) 0.0028(9) 0.0065(9) -0.0003(9)
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
O6 N2 O5 124.60(19)
O6 N2 C5 117.81(19)
O5 N2 C5 117.59(18)
O4 N1 O3 123.6(2)
O4 N1 C1 117.62(19)
O3 N1 C1 118.74(18)
C2 C3 C4 120.50(19)
C2 C3 C7 119.80(18)
C4 C3 C7 119.67(18)
C5 C4 C3 118.6(2)
O1 C7 O2 124.9(2)
O1 C7 C3 118.3(2)
O2 C7 C3 116.85(19)
C1 C6 C5 116.37(19)
C1 C2 C3 118.23(19)
C6 C1 C2 123.2(2)
C6 C1 N1 118.14(18)
C2 C1 N1 118.61(18)
C4 C5 C6 123.07(19)
C4 C5 N2 118.32(19)
C6 C5 N2 118.60(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O3 N1 1.214(2)
O1 C7 1.252(3)
O6 N2 1.218(2)
O2 C7 1.271(3)
N2 O5 1.219(2)
N2 C5 1.476(3)
N1 O4 1.209(3)
N1 C1 1.475(3)
C3 C2 1.387(3)
C3 C4 1.389(3)
C3 C7 1.493(3)
C4 C5 1.375(3)
C6 C1 1.377(3)
C6 C5 1.383(3)
C2 C1 1.383(3)
