#------------------------------------------------------------------------------
#$Date: 2018-10-05 15:19:55 +0300 (Fri, 05 Oct 2018) $
#$Revision: 211332 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/04/7150482.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_7150482
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         'C16 H14 N4, C8H6O4'
_chemical_formula_sum            'C24 H20 N4 O4'
_chemical_formula_weight         428.44
_chemical_melting_point          211.5(5)
_chemical_name_systematic
; 
N,N'-bis(2-pyridyl)-1,3-diaminobenzene 1,3-benzenedicarboxylic acid  
;
_space_group_IT_number           57
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2c 2b'
_symmetry_space_group_name_H-M   'P b c m'
_atom_sites_solution_hydrogens   mixed
_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                   9.1922(11)
_cell_length_b                   7.1341(11)
_cell_length_c                   31.750(4)
_cell_measurement_reflns_used    'not relevant with the CCD data'
_cell_measurement_temperature    296(2)
_cell_volume                     2082.1(5)
_computing_cell_refinement       'KM4RED, Version 1.157a, 1999'
_computing_data_collection       'KM4CCD, Version 1.157a, 1999'
_computing_data_reduction        'KM4RED, Version 1.157a, 1999'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Kuma KM4CCD diffractometer'
_diffrn_measurement_method       'ο 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  0.0714
_diffrn_reflns_av_sigmaI/netI    0.0242
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            10774
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         4.10
_diffrn_standards_decay_%        <2
_diffrn_standards_interval_count 50
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       0.0054(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.170
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         1867
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.170
_refine_ls_R_factor_all          0.0701
_refine_ls_R_factor_gt           0.0666
_refine_ls_shift/su_max          0.014
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0616P)²+1.3617P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1534
_refine_ls_wR_factor_ref         0.1577
_reflns_number_gt                1766
_reflns_number_total             1867
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b211675h.txt
_cod_data_source_block           1iso
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '211-212' was changed to '211.5(5)' -
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1569 2011-02-09 13:29:24Z adriana 

The following automatic conversions were performed:

'_atom_sites_solution_hydrogens' value 'difmap and geom' was changed
to 'mixed'.

Automatic conversion script
Id: cif_fix_values 6452 2018-10-05 10:23:21Z andrius 
;
_cod_original_sg_symbol_H-M      Pbcm
_cod_database_code               7150482
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x, -y+1/2, -z'
'-x, -y, -z'
'x, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x, 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 1.1603(2) 0.0050(3) 0.62749(6) 0.0447(5) Uani 1 1 d . . .
N7 N 0.9793(2) 0.0944(3) 0.67283(6) 0.0437(5) Uani 1 1 d . . .
H7 H 0.9183 0.0706 0.6489 0.073(9) Uiso 1 1 d R . .
C2 C 1.1248(2) 0.0956(3) 0.66313(7) 0.0400(5) Uani 1 1 d . . .
C3 C 1.2324(3) 0.1869(3) 0.68681(7) 0.0450(6) Uani 1 1 d . . .
H3 H 1.2069 0.2579 0.7114 0.057(8) Uiso 1 1 d R . .
C4 C 1.3741(3) 0.1781(4) 0.67372(8) 0.0524(7) Uani 1 1 d . . .
H4 H 1.4454 0.2476 0.6894 0.066(8) Uiso 1 1 d R . .
C5 C 1.4113(3) 0.0784(4) 0.63769(8) 0.0567(7) Uani 1 1 d . . .
H5 H 1.5094 0.0748 0.6274 0.070(9) Uiso 1 1 d R . .
C6 C 1.3000(3) -0.0015(4) 0.61548(8) 0.0514(7) Uani 1 1 d . . .
H6 H 1.3155 -0.0628 0.5890 0.060(8) Uiso 1 1 d R . .
C8 C 0.9137(2) 0.1329(3) 0.71198(6) 0.0383(5) Uani 1 1 d . . .
C9 C 0.7703(3) 0.1954(3) 0.71202(7) 0.0443(6) Uani 1 1 d . . .
H9 H 0.7197 0.2173 0.6860 0.054(7) Uiso 1 1 d R . .
C10 C 0.7005(4) 0.2247(6) 0.7500 0.0491(9) Uani 1 2 d S . .
H10 H 0.6016 0.2683 0.7500 0.037(8) Uiso 1 2 d SR . .
C11 C 0.9845(3) 0.0961(4) 0.7500 0.0367(7) Uani 1 2 d S . .
H11 H 1.0818 0.0471 0.7500 0.039(9) Uiso 1 2 d SR . .
O2A O 0.7922(2) -0.0082(3) 0.59909(5) 0.0601(6) Uani 1 1 d . . .
O1A O 0.9906(2) -0.1305(3) 0.56933(6) 0.0655(6) Uani 1 1 d . . .
H1OA H 1.044(4) -0.074(5) 0.5955(11) 0.080(10) Uiso 1 1 d . . .
C1A C 0.7707(3) -0.1731(3) 0.53387(7) 0.0454(6) Uani 1 1 d . . .
C2A C 0.8453(4) -0.2500 0.5000 0.0479(8) Uani 1 2 d S . .
H2A H 0.9497 -0.2500 0.5000 0.052(10) Uiso 1 2 d SR . .
C3A C 0.5434(4) -0.2500 0.5000 0.0585(10) Uani 1 2 d S . .
H3A H 0.4389 -0.2500 0.5000 0.057(10) Uiso 1 2 d SR . .
C4A C 0.6191(3) -0.1726(4) 0.53342(8) 0.0533(7) Uani 1 1 d . . .
H4A H 0.5729 -0.1147 0.5572 0.056(7) Uiso 1 1 d R . .
C5A C 0.8509(3) -0.0946(4) 0.57065(7) 0.0498(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
C6 N1 C2 119.2(2) . . ?
C2 N7 C8 127.88(19) . . ?
C2 N7 H7 113.1 . . ?
C8 N7 H7 118.9 . . ?
N1 C2 N7 115.0(2) . . ?
N1 C2 C3 120.3(2) . . ?
N7 C2 C3 124.7(2) . . ?
C4 C3 C2 119.1(2) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.6 . . ?
C3 C4 C5 120.5(2) . . ?
C3 C4 H4 117.9 . . ?
C5 C4 H4 121.5 . . ?
C6 C5 C4 117.0(2) . . ?
C6 C5 H5 121.0 . . ?
C4 C5 H5 121.7 . . ?
N1 C6 C5 123.8(2) . . ?
N1 C6 H6 114.0 . . ?
C5 C6 H6 122.1 . . ?
C9 C8 C11 120.1(2) . . ?
C9 C8 N7 117.97(19) . . ?
C11 C8 N7 121.8(2) . . ?
C10 C9 C8 119.3(2) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.7 . . ?
C9 C10 C9 121.5(3) 6_557 . ?
C9 C10 H10 119.2 6_557 . ?
C9 C10 H10 119.2 . . ?
C8 C11 C8 119.7(3) 6_557 . ?
C8 C11 H11 120.2 6_557 . ?
C8 C11 H11 120.2 . . ?
C5A O1A H1OA 111.1(18) . . ?
C2A C1A C4A 119.1(2) . . ?
C2A C1A C5A 120.8(2) . . ?
C4A C1A C5A 120.1(2) . . ?
C1A C2A C1A 120.8(3) 4_546 . ?
C1A C2A H2A 119.6 4_546 . ?
C1A C2A H2A 119.6 . . ?
C4A C3A C4A 119.6(3) . 4_546 ?
C4A C3A H3A 120.2 . . ?
C4A C3A H3A 120.2 4_546 . ?
C3A C4A C1A 120.7(2) . . ?
C3A C4A H4A 123.5 . . ?
C1A C4A H4A 115.8 . . ?
O2A C5A O1A 123.8(2) . . ?
O2A C5A C1A 123.5(2) . . ?
O1A C5A C1A 112.7(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 C6 1.341(3) . ?
N1 C2 1.343(3) . ?
N7 C2 1.373(3) . ?
N7 C8 1.409(3) . ?
N7 H7 0.9600 . ?
C2 C3 1.403(3) . ?
C3 C4 1.368(3) . ?
C3 H3 0.9601 . ?
C4 C5 1.390(4) . ?
C4 H4 0.9600 . ?
C5 C6 1.366(4) . ?
C5 H5 0.9600 . ?
C6 H6 0.9599 . ?
C8 C9 1.392(3) . ?
C8 C11 1.396(3) . ?
C9 C10 1.382(3) . ?
C9 H9 0.9600 . ?
C10 C9 1.382(3) 6_557 ?
C10 H10 0.9600 . ?
C11 C8 1.396(3) 6_557 ?
C11 H11 0.9600 . ?
O2A C5A 1.219(3) . ?
O1A C5A 1.310(3) . ?
O1A H1OA 1.05(4) . ?
C1A C2A 1.388(3) . ?
C1A C4A 1.394(4) . ?
C1A C5A 1.490(3) . ?
C2A C1A 1.388(3) 4_546 ?
C2A H2A 0.9600 . ?
C3A C4A 1.384(3) . ?
C3A C4A 1.384(3) 4_546 ?
C3A H3A 0.9600 . ?
C4A H4A 0.9600 . ?
