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#$Date: 2016-03-26 14:09:35 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180290 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/04/7150489.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_7150489
loop_
_publ_author_name
'Bensemann, Igor'
'Gdaniec, Maria'
'Łakomecka, Karina'
'Milewska, Maria J.'
'Połoński, Tadeusz'
_publ_section_title
;
 Creation of hydrogen bonded 1D networks by co-crystallization of
 N,N'-bis(2-pyridyl)aryldiamines with dicarboxylic acidsSupramolecular
 structures formed by 2-aminopyridine derivatives. Part II.5
;
_journal_issue                   8
_journal_name_full               'Organic &  Biomolecular Chemistry'
_journal_page_first              1425
_journal_paper_doi               10.1039/b211675h
_journal_volume                  1
_journal_year                    2003
_chemical_formula_moiety         'C16H14N4, C14H10O4'
_chemical_formula_sum            'C30 H24 N4 O4'
_chemical_formula_weight         504.53
_chemical_melting_point          216
_chemical_name_systematic
; 
N,N'-bis(2-pyridyl)-1,4-diaminobenzene 2,2'-biphenyldicarboxylic acid co-crystal
;
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_atom_sites_solution_hydrogens   dimap,geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.117(2)
_cell_length_b                   14.433(4)
_cell_length_c                   19.312(6)
_cell_measurement_reflns_used    34
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      14
_cell_measurement_theta_min      7
_cell_volume                     2541.2(12)
_computing_cell_refinement       'Kuma KM-4 software (Kuma Diffraction, 1991)'
_computing_data_collection       'Kuma KM-4 sofware (Kuma Diffraction, 1991)'
_computing_data_reduction        'Kuma KM-4 software (Kuma Diffraction, 1991)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'KM-4 four-circle diffractometer'
_diffrn_measurement_method       'ω/2θ 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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0571
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2258
_diffrn_reflns_theta_full        25.06
_diffrn_reflns_theta_max         25.06
_diffrn_reflns_theta_min         2.11
_diffrn_standards_decay_%        <1.5
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.142
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.0095(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.981
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     197
_refine_ls_number_reflns         2258
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.981
_refine_ls_R_factor_all          0.1369
_refine_ls_R_factor_gt           0.0398
_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)+(0.0586P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0977
_refine_ls_wR_factor_ref         0.1129
_reflns_number_gt                1208
_reflns_number_total             2258
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b211675h.txt
_cod_data_source_block           2diph
_cod_original_sg_symbol_H-M      Pbcn
_cod_database_code               7150489
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N -0.80616(18) -0.23704(12) 0.37850(10) 0.0550(5) Uani 1 1 d . . .
C2 C -0.7815(2) -0.16667(15) 0.42167(12) 0.0540(6) Uani 1 1 d . . .
C3 C -0.8981(2) -0.11778(17) 0.45110(14) 0.0679(7) Uani 1 1 d . . .
H3 H -0.8774 -0.0684 0.4829 0.098(9) Uiso 1 1 d R . .
C4 C -1.0374(3) -0.13947(18) 0.43109(16) 0.0788(8) Uani 1 1 d . . .
H4 H -1.1206 -0.1060 0.4485 0.115(10) Uiso 1 1 d R . .
C5 C -1.0625(3) -0.20971(17) 0.38504(16) 0.0793(8) Uani 1 1 d . . .
H5 H -1.1541 -0.2304 0.3660 0.086(8) Uiso 1 1 d R . .
C6 C -0.9453(3) -0.25735(17) 0.36129(14) 0.0684(7) Uani 1 1 d . . .
H6 H -0.9480 -0.3070 0.3283 0.089(9) Uiso 1 1 d R . .
C8 C -0.5737(2) -0.07363(14) 0.46874(11) 0.0475(5) Uani 1 1 d . . .
C10 C -0.6281(2) 0.01551(14) 0.46422(11) 0.0537(6) Uani 1 1 d . . .
H10 H -0.7146 0.0273 0.4373 0.077(7) Uiso 1 1 d R . .
C9 C -0.4442(2) -0.08785(15) 0.50460(10) 0.0508(5) Uani 1 1 d . . .
H9 H -0.4061 -0.1498 0.5069 0.045(5) Uiso 1 1 d R . .
N7 N -0.63698(17) -0.15036(12) 0.43526(10) 0.0605(5) Uani 1 1 d . . .
H7 H -0.5680 -0.1980 0.4233 0.072(7) Uiso 1 1 d R . .
O1A O -0.6227(2) -0.3623(3) 0.3370(2) 0.0784(13) Uani 0.898(10) 1 d P . .
H1OA H -0.681(3) -0.2970(19) 0.3504(14) 0.110(9) Uiso 1 1 d . . .
O2A O -0.4334(3) -0.2834(3) 0.3772(3) 0.0923(13) Uani 0.898(10) 1 d P . .
O1A' O -0.587(2) -0.3232(14) 0.3093(8) 0.038(6) Uiso 0.102(10) 1 d P . .
O2A' O -0.470(3) -0.3195(16) 0.4023(10) 0.057(7) Uiso 0.102(10) 1 d P . .
C1A C -0.42737(19) -0.48587(13) 0.26712(11) 0.0460(5) Uani 1 1 d . . .
C2A C -0.3860(2) -0.42437(13) 0.31985(11) 0.0475(5) Uani 1 1 d . . .
C3A C -0.2470(2) -0.43313(16) 0.34883(12) 0.0604(6) Uani 1 1 d . . .
H3A H -0.2237 -0.3913 0.3859 0.063(7) Uiso 1 1 d R . .
C4A C -0.1522(2) -0.50041(17) 0.32819(14) 0.0714(7) Uani 1 1 d . . .
H4A H -0.0528 -0.5045 0.3443 0.079(7) Uiso 1 1 d R . .
C5A C -0.1930(2) -0.56164(17) 0.27790(14) 0.0699(7) Uani 1 1 d . . .
H5A H -0.1296 -0.6104 0.2622 0.088(8) Uiso 1 1 d R . .
C6A C -0.3303(2) -0.55421(15) 0.24826(13) 0.0605(6) Uani 1 1 d . . .
H6A H -0.3596 -0.5980 0.2135 0.079(8) Uiso 1 1 d R . .
C7A C -0.4818(2) -0.35039(16) 0.34668(12) 0.0555(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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C6 118.7(2) . . ?
N1 C2 N7 114.52(19) . . ?
N1 C2 C3 120.72(19) . . ?
N7 C2 C3 124.7(2) . . ?
C4 C3 C2 118.5(2) . . ?
C3 C4 C5 120.7(2) . . ?
C6 C5 C4 117.8(2) . . ?
N1 C6 C5 123.5(2) . . ?
C10 C8 C9 118.41(19) . . ?
C10 C8 N7 123.86(19) . . ?
C9 C8 N7 117.59(18) . . ?
C9 C10 C8 120.5(2) 5_456 . ?
C10 C9 C8 121.1(2) 5_456 . ?
C2 N7 C8 128.36(18) . . ?
O1A' O1A C7A 68.1(10) . . ?
O2A' O2A C7A 67.6(16) . . ?
O1A O1A' C7A 73.8(11) . . ?
O2A O2A' C7A 74.0(15) . . ?
C6A C1A C2A 118.27(18) . . ?
C6A C1A C1A 117.23(18) . 3_455 ?
C2A C1A C1A 124.39(17) . 3_455 ?
C3A C2A C1A 118.65(19) . . ?
C3A C2A C7A 117.65(19) . . ?
C1A C2A C7A 123.70(17) . . ?
C4A C3A C2A 121.7(2) . . ?
C3A C4A C5A 119.9(2) . . ?
C4A C5A C6A 119.5(2) . . ?
C1A C6A C5A 122.0(2) . . ?
O2A' C7A O2A 38.4(11) . . ?
O2A' C7A O1A' 118.5(11) . . ?
O2A C7A O1A' 107.8(8) . . ?
O2A' C7A O1A 105.8(12) . . ?
O2A C7A O1A 121.9(2) . . ?
O1A' C7A O1A 38.1(10) . . ?
O2A' C7A C2A 123.0(9) . . ?
O2A C7A C2A 122.2(2) . . ?
O1A' C7A C2A 118.3(6) . . ?
O1A C7A C2A 115.9(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.333(3) . ?
N1 C6 1.344(3) . ?
C2 N7 1.364(2) . ?
C2 C3 1.397(3) . ?
C3 C4 1.364(3) . ?
C4 C5 1.368(4) . ?
C5 C6 1.351(3) . ?
C8 C10 1.382(3) . ?
C8 C9 1.384(3) . ?
C8 N7 1.406(3) . ?
C10 C9 1.374(3) 5_456 ?
C9 C10 1.374(3) 5_456 ?
O1A O1A' 0.84(2) . ?
O1A C7A 1.310(3) . ?
O2A O2A' 0.78(2) . ?
O2A C7A 1.215(3) . ?
O1A' C7A 1.266(14) . ?
O2A' C7A 1.17(2) . ?
C1A C6A 1.374(3) . ?
C1A C2A 1.402(3) . ?
C1A C1A 1.480(4) 3_455 ?
C2A C3A 1.391(3) . ?
C2A C7A 1.473(3) . ?
C3A C4A 1.359(3) . ?
C4A C5A 1.365(3) . ?
C5A C6A 1.380(3) . ?
