#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:12:59 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179656 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/09/4510966.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_4510966
loop_
_publ_author_name
'Thomas, Lynne H.'
'Blagden, Nicholas'
'Gutmann, Matthias J.'
'Kallay, Andras A.'
'Parkin, Andrew'
'Seaton, Colin C.'
'Wilson, Chick C.'
_publ_section_title
;
 Tuning Proton Behavior in a Ternary Molecular Complex
;
_journal_issue                   6
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              2770
_journal_paper_doi               10.1021/cg100315u
_journal_volume                  10
_journal_year                    2010
_chemical_compound_source        'crystallisation from solvent'
_chemical_formula_moiety         'C9 H11 N O2, 0.5(C10 H8 N2), C7 H4 N2 O6'
_chemical_formula_sum            'C21 H19 N4 O8'
_chemical_formula_weight         455
_chemical_name_common
'3,5-dinitrobenzoic acid - 4,4'-bipyridine - 4-(dimethylamino)benzoic acid'
_chemical_name_systematic
'3,5-dinitrobenzoic acid - 4,4'-bipyridine - 4-(dimethylamino)benzoic acid'
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2010-01-07T17:35:28-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                79.944(15)
_cell_angle_beta                 82.471(16)
_cell_angle_gamma                87.756(17)
_cell_formula_units_Z            2
_cell_length_a                   7.7483(19)
_cell_length_b                   8.670(2)
_cell_length_c                   15.523(4)
_cell_measurement_temperature    200(2)
_cell_volume                     1017.8(4)
_computing_cell_refinement       SXD-2001
_computing_data_collection       SXD-2001
_computing_data_reduction        SXD-2001
_computing_molecular_graphics    'Mercury (McRae, 2008)'
_computing_publication_material  'WinGX (Farrugia, 2007)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_pressure         101.325
_diffrn_ambient_temperature      200(2)
_diffrn_measurement_device_type  'SXD time-of-flight LAUE diffraction'
_diffrn_measurement_method       'time-of-flight LAUE diffraction'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          neutron
_diffrn_radiation_source         'ISIS spallation source'
_diffrn_radiation_type           neutron
_diffrn_radiation_wavelength     0.7-6.9
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_unetI/netI     0.1149
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            5221
_diffrn_source                   synchrotron
_diffrn_source_type              'SXD, ISIS'
_exptl_absorpt_coefficient_mu    0.129
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.486
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             305
_exptl_crystal_recrystallization_method
'co-crystals grown from methanol using the ReactArray Microvate'
_exptl_crystal_size_max          5
_exptl_crystal_size_mid          2
_exptl_crystal_size_min          2
_refine_diff_density_max         1.027
_refine_diff_density_min         -1.103
_refine_diff_density_rms         0.251
_refine_ls_extinction_coef       0.0101(4)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.347
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     471
_refine_ls_number_reflns         5221
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.347
_refine_ls_R_factor_all          0.1009
_refine_ls_R_factor_gt           0.088
_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)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.2057
_reflns_number_gt                4385
_reflns_number_total             5221
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            neutronVT.cif
_cod_data_source_block           neutron_200K
_cod_database_code               4510966
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_type_symbol
H11 0.0042(12) 0.7748(13) 0.8038(6) 0.060(3) Uani d 1 H
H3 0.3871(11) 0.1631(12) 0.2146(5) 0.045(2) Uani d 1 H
H12 0.3557(13) 1.1301(13) 0.6565(6) 0.062(3) Uani d 1 H
H1 0.5883(12) 0.6257(12) 0.1160(5) 0.045(2) Uani d 1 H
H2 0.7723(12) 0.2390(11) -0.0149(5) 0.046(2) Uani d 1 H
H17 0.2965(18) 1.2448(17) 0.7749(9) 0.088(4) Uani d 1 H
H13 0.4816(13) 0.9451(14) 0.5654(5) 0.068(3) Uani d 1 H
H15 -0.017(2) 1.085(3) 0.9169(11) 0.122(6) Uani d 1 H
H10 0.1299(13) 0.5916(13) 0.7094(6) 0.062(3) Uani d 1 H
H7 0.2108(15) 1.1176(13) 0.3873(7) 0.074(4) Uani d 1 H
H6 -0.1119(18) 0.7435(15) 0.5342(7) 0.099(5) Uani d 1 H
H8 0.3389(15) 0.9282(14) 0.2927(7) 0.077(4) Uani d 1 H
H18 0.103(3) 1.2925(16) 0.8250(12) 0.138(8) Uani d 1 H
H19 0.138(2) 1.2918(17) 0.7125(9) 0.111(6) Uani d 1 H
H14 -0.026(3) 0.920(3) 0.8973(12) 0.136(8) Uani d 1 H
H16 -0.1516(15) 1.054(4) 0.8478(9) 0.234(18) Uani d 1 H
H5 0.030(2) 0.5705(14) 0.4324(8) 0.096(5) Uani d 1 H
H4 0.2865(13) 0.6510(12) 0.2961(6) 0.058(3) Uani d 1 H
H9 0.574(2) 0.6031(19) 0.4696(9) 0.103(6) Uani d 1 H
O4 0.2661(7) 0.3709(7) 0.3001(3) 0.0451(14) Uani d 1 O
O8 0.4796(7) -0.0629(7) 0.1467(3) 0.0394(12) Uani d 1 O
O5 0.8097(8) 0.6827(7) -0.0117(4) 0.0586(18) Uani d 1 O
O3 0.3681(8) 0.6076(7) 0.2421(3) 0.0484(15) Uani d 1 O
O7 0.6767(7) -0.0238(7) 0.0337(3) 0.0411(13) Uani d 1 O
O6 0.8870(7) 0.4935(7) -0.0810(3) 0.0435(14) Uani d 1 O
C4 0.6930(5) 0.2847(5) 0.0381(2) 0.0256(9) Uani d 1 C
C5 0.5816(5) 0.1882(5) 0.1002(2) 0.0240(8) Uani d 1 C
N4 0.5792(4) 0.0208(4) 0.09312(17) 0.0297(7) Uani d 1 N
C3 0.6913(4) 0.4408(5) 0.0461(2) 0.0248(9) Uani d 1 C
C2 0.5868(5) 0.5023(5) 0.1120(2) 0.0241(9) Uani d 1 C
C6 0.4737(5) 0.2423(5) 0.1671(2) 0.0257(9) Uani d 1 C
N3 0.8037(4) 0.5470(4) -0.02020(17) 0.0325(7) Uani d 1 N
C1 0.4759(5) 0.4010(5) 0.1735(2) 0.0252(9) Uani d 1 C
C7 0.3581(5) 0.4574(5) 0.2466(2) 0.0284(9) Uani d 1 C
O1 0.3387(8) 0.5049(8) 0.5866(4) 0.0513(16) Uani d 1 O
N1 0.1065(4) 1.0710(5) 0.79373(19) 0.0462(10) Uani d 1 N
C18 0.3764(5) 0.9080(6) 0.6178(2) 0.0378(12) Uani d 1 C
O2 0.5145(8) 0.6938(8) 0.5120(4) 0.0491(17) Uani d 1 O
C16 0.1711(5) 0.9695(5) 0.7404(2) 0.0290(10) Uani d 1 C
C14 0.1805(5) 0.7099(6) 0.6984(2) 0.0351(11) Uani d 1 C
C21 0.1606(8) 1.2328(7) 0.7764(3) 0.0469(13) Uani d 1 C
C15 0.1102(5) 0.8148(6) 0.7523(2) 0.0349(11) Uani d 1 C
C13 0.3161(5) 0.7531(6) 0.6306(2) 0.0333(11) Uani d 1 C
C17 0.3069(5) 1.0143(6) 0.6703(2) 0.0364(12) Uani d 1 C
C19 0.3934(6) 0.6448(6) 0.5743(2) 0.0383(12) Uani d 1 C
C20 -0.0332(7) 1.0291(9) 0.8659(4) 0.0468(13) Uani d 1 C
N2 0.1897(4) 0.7429(4) 0.35959(17) 0.0327(7) Uani d 1 N
C9 -0.0119(6) 0.7918(6) 0.4821(2) 0.0409(12) Uani d 1 C
C10 0.0394(4) 0.9462(5) 0.4706(2) 0.0221(8) Uani d 1 C
C12 0.2385(6) 0.8921(6) 0.3477(2) 0.0377(11) Uani d 1 C
C11 0.1672(5) 0.9972(5) 0.4008(2) 0.0313(10) Uani d 1 C
C8 0.0659(7) 0.6940(6) 0.4249(3) 0.0448(12) Uani d 1 C
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0 0 '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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0 0 '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
_geom_angle_site_symmetry_3
C3 C4 C5 116.4(4) .
C6 C5 C4 123.0(4) .
C6 C5 N4 119.2(3) .
C4 C5 N4 117.8(3) .
O8 N4 O7 124.6(5) .
O8 N4 C5 117.7(4) .
O7 N4 C5 117.7(4) .
C4 C3 C2 123.4(4) .
C4 C3 N3 117.7(3) .
C2 C3 N3 118.8(4) .
C3 C2 C1 118.5(4) .
C5 C6 C1 119.1(3) .
O5 N3 O6 123.2(4) .
O5 N3 C3 118.5(4) .
O6 N3 C3 118.3(4) .
C6 C1 C2 119.6(4) .
C6 C1 C7 118.3(3) .
C2 C1 C7 122.1(4) .
O4 C7 O3 126.2(5) .
O4 C7 C1 122.2(5) .
O3 C7 C1 111.6(4) .
C16 N1 C21 121.2(3) .
C16 N1 C20 122.2(4) .
C21 N1 C20 116.4(5) .
C17 C18 C13 122.1(4) .
N1 C16 C15 122.0(3) .
N1 C16 C17 120.8(4) .
C15 C16 C17 117.3(4) .
C15 C14 C13 121.2(4) .
C14 C15 C16 121.6(3) .
C14 C13 C18 117.5(5) .
C14 C13 C19 122.1(4) .
C18 C13 C19 120.3(3) .
C18 C17 C16 120.4(4) .
O1 C19 O2 121.5(6) .
O1 C19 C13 119.8(4) .
O2 C19 C13 118.7(5) .
C8 N2 C12 118.2(4) .
C10 C9 C8 119.8(3) .
C9 C10 C11 117.5(4) .
C9 C10 C10 121.6(4) 2_576
C11 C10 C10 120.9(4) 2_576
N2 C12 C11 123.2(3) .
C12 C11 C10 119.0(4) .
N2 C8 C9 122.3(4) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O4 C7 . 1.196(6)
O8 N4 . 1.216(5)
O5 N3 . 1.210(7)
O3 C7 . 1.297(7)
O7 N4 . 1.221(5)
O6 N3 . 1.221(6)
C4 C3 . 1.380(6)
C4 C5 . 1.389(5)
C5 C6 . 1.383(5)
C5 N4 . 1.475(5)
C3 C2 . 1.388(5)
C3 N3 . 1.471(4)
C2 C1 . 1.404(5)
C6 C1 . 1.397(6)
C1 C7 . 1.499(5)
O1 C19 . 1.275(7)
N1 C16 . 1.350(6)
N1 C21 . 1.449(7)
N1 C20 . 1.459(6)
C18 C17 . 1.383(7)
C18 C13 . 1.412(7)
O2 C19 . 1.282(6)
C16 C15 . 1.413(6)
C16 C17 . 1.423(5)
C14 C15 . 1.389(7)
C14 C13 . 1.399(5)
C13 C19 . 1.452(7)
N2 C8 . 1.325(5)
N2 C12 . 1.336(6)
C9 C10 . 1.386(6)
C9 C8 . 1.398(6)
C10 C11 . 1.392(5)
C10 C10 2_576 1.476(8)
C12 C11 . 1.386(6)
