#------------------------------------------------------------------------------
#$Date: 2018-10-05 15:19:55 +0300 (Fri, 05 Oct 2018) $
#$Revision: 211332 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/04/7150483.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_7150483
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, C14H10O5'
_chemical_formula_sum            'C30 H24 N4 O5'
_chemical_formula_weight         520.53
_chemical_melting_point          179(2)
_chemical_name_systematic
; 
N,N'-bis(2-pyridyl)-1,3-diaminobenzene 4,4'-oxybisbenzoic acid 
;
_space_group_IT_number           40
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'A 2 -2a'
_symmetry_space_group_name_H-M   'A m a 2'
_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                   35.743(7)
_cell_length_b                   9.285(2)
_cell_length_c                   7.3380(10)
_cell_measurement_reflns_used    'not relevant with the CCD data'
_cell_measurement_temperature    100(2)
_cell_volume                     2435.3(8)
_computing_cell_refinement       'KM4RED, Version 1.163, 2000'
_computing_data_collection       'KM4CCD, Version 1.163, 2000'
_computing_data_reduction        'KM4RED, Version 1.163, 2000'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.963
_diffrn_measured_fraction_theta_max 0.963
_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  0.0551
_diffrn_reflns_av_sigmaI/netI    0.0537
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            3651
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         3.42
_diffrn_standards_decay_%        <2
_diffrn_standards_interval_count 50
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         1135
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.985
_refine_ls_R_factor_all          0.0550
_refine_ls_R_factor_gt           0.0371
_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)+(0.0494P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0788
_refine_ls_wR_factor_ref         0.0836
_reflns_number_gt                909
_reflns_number_total             1135
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b211675h.txt
_cod_data_source_block           1obe
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '158-200' was changed to '179(2)' -
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      Ama2
_cod_database_code               7150483
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'x+1/2, -y, z'
'-x+1/2, y, z'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/2, -y+1/2, z+1/2'
'-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
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.35603(7) 0.1951(3) 0.6846(4) 0.0210(7) Uani 1 1 d . . .
C2 C 0.32609(8) 0.1615(4) 0.7862(4) 0.0190(8) Uani 1 1 d . . .
C3 C 0.30585(9) 0.2671(4) 0.8791(5) 0.0225(9) Uani 1 1 d . . .
H3 H 0.2841 0.2458 0.9554 0.022(9) Uiso 1 1 d R . .
C4 C 0.31518(9) 0.4095(4) 0.8541(5) 0.0240(9) Uani 1 1 d . . .
H4 H 0.3010 0.4913 0.9241 0.037(10) Uiso 1 1 d R . .
C5 C 0.34495(9) 0.4461(4) 0.7387(5) 0.0246(9) Uani 1 1 d . . .
H5 H 0.3537 0.5520 0.7080 0.030(10) Uiso 1 1 d R . .
C6 C 0.36455(8) 0.3357(4) 0.6619(4) 0.0225(8) Uani 1 1 d . . .
H6 H 0.3859 0.3547 0.5793 0.040(11) Uiso 1 1 d R . .
N7 N 0.31838(7) 0.0166(3) 0.7964(4) 0.0211(7) Uani 1 1 d . . .
H7 H 0.3376 -0.0383 0.7846 0.027(10) Uiso 1 1 d R . .
C8 C 0.28377(8) -0.0489(4) 0.8260(4) 0.0187(8) Uani 1 1 d . . .
C9 C 0.28361(8) -0.1966(4) 0.8675(5) 0.0221(9) Uani 1 1 d . . .
H9 H 0.3067 -0.2446 0.8787 0.010(8) Uiso 1 1 d R . .
C10 C 0.2500 -0.2669(6) 0.8855(7) 0.0230(12) Uani 1 2 d S . .
H10 H 0.2500 -0.3719 0.9038 0.027(14) Uiso 1 2 d SR . .
C11 C 0.2500 0.0234(5) 0.8027(7) 0.0192(11) Uani 1 2 d S . .
H11 H 0.2500 0.1328 0.7652 0.010(11) Uiso 1 2 d SR . .
O1A O 0.40711(6) 0.0211(3) 0.5444(3) 0.0226(6) Uani 1 1 d . . .
H1OA H 0.3838(9) 0.085(4) 0.598(5) 0.030(10) Uiso 1 1 d . . .
O2A O 0.38230(6) -0.1573(3) 0.7106(4) 0.0283(6) Uani 1 1 d . . .
C1A C 0.43165(8) -0.2134(4) 0.5069(4) 0.0178(8) Uani 1 1 d . . .
C2A C 0.43115(8) -0.3590(4) 0.5518(5) 0.0235(9) Uani 1 1 d . . .
H2A H 0.4145 -0.3840 0.6398 0.038(11) Uiso 1 1 d R . .
C3A C 0.45421(8) -0.4551(4) 0.4627(5) 0.0226(8) Uani 1 1 d . . .
H3A H 0.4555 -0.5591 0.4915 0.020(9) Uiso 1 1 d R . .
C4A C 0.47817(8) -0.4045(4) 0.3290(5) 0.0214(8) Uani 1 1 d . . .
C5A C 0.47971(8) -0.2599(4) 0.2842(5) 0.0244(9) Uani 1 1 d . . .
H5A H 0.4984 -0.2287 0.1932 0.041(10) Uiso 1 1 d R . .
C6A C 0.45644(8) -0.1639(4) 0.3736(5) 0.0209(8) Uani 1 1 d . . .
H6A H 0.4573 -0.0577 0.3416 0.011(8) Uiso 1 1 d R . .
C7A C 0.40494(9) -0.1150(4) 0.5978(5) 0.0227(8) Uani 1 1 d . . .
O3A O 0.5000 -0.5000 0.2301(5) 0.0249(8) Uani 1 2 d S . .
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 118.3(3) . . ?
N1 C2 N7 114.7(3) . . ?
N1 C2 C3 121.4(3) . . ?
N7 C2 C3 123.8(3) . . ?
C4 C3 C2 119.0(3) . . ?
C4 C3 H3 117.6 . . ?
C2 C3 H3 123.3 . . ?
C3 C4 C5 119.8(3) . . ?
C3 C4 H4 120.9 . . ?
C5 C4 H4 119.2 . . ?
C6 C5 C4 117.2(3) . . ?
C6 C5 H5 117.4 . . ?
C4 C5 H5 125.4 . . ?
N1 C6 C5 124.0(3) . . ?
N1 C6 H6 114.9 . . ?
C5 C6 H6 121.0 . . ?
C2 N7 C8 127.7(3) . . ?
C2 N7 H7 114.4 . . ?
C8 N7 H7 117.8 . . ?
C11 C8 N7 122.7(3) . . ?
C11 C8 C9 119.6(3) . . ?
N7 C8 C9 117.5(3) . . ?
C10 C9 C8 119.2(3) . . ?
C10 C9 H9 122.2 . . ?
C8 C9 H9 118.6 . . ?
C9 C10 C9 122.0(5) 4 . ?
C9 C10 H10 118.9 4 . ?
C9 C10 H10 118.9 . . ?
C8 C11 C8 120.3(4) 4 . ?
C8 C11 H11 119.8 4 . ?
C8 C11 H11 119.8 . . ?
C7A O1A H1OA 111.4(19) . . ?
C2A C1A C6A 119.6(3) . . ?
C2A C1A C7A 119.0(3) . . ?
C6A C1A C7A 121.4(3) . . ?
C3A C2A C1A 120.5(3) . . ?
C3A C2A H2A 124.3 . . ?
C1A C2A H2A 115.2 . . ?
C2A C3A C4A 119.1(4) . . ?
C2A C3A H3A 123.9 . . ?
C4A C3A H3A 116.9 . . ?
C5A C4A C3A 121.5(3) . . ?
C5A C4A O3A 118.3(3) . . ?
C3A C4A O3A 120.2(3) . . ?
C4A C5A C6A 119.3(3) . . ?
C4A C5A H5A 118.2 . . ?
C6A C5A H5A 122.5 . . ?
C5A C6A C1A 120.0(3) . . ?
C5A C6A H6A 119.9 . . ?
C1A C6A H6A 120.0 . . ?
O2A C7A O1A 123.0(3) . . ?
O2A C7A C1A 122.2(3) . . ?
O1A C7A C1A 114.7(3) . . ?
C4A O3A C4A 116.9(4) . 2_645 ?
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 1.341(4) . ?
N1 C6 1.350(4) . ?
C2 N7 1.375(4) . ?
C2 C3 1.396(5) . ?
C3 C4 1.376(5) . ?
C3 H3 0.9790 . ?
C4 C5 1.402(5) . ?
C4 H4 1.0479 . ?
C5 C6 1.363(5) . ?
C5 H5 1.0563 . ?
C6 H6 0.9891 . ?
N7 C8 1.396(4) . ?
N7 H7 0.8608 . ?
C8 C11 1.391(4) . ?
C8 C9 1.405(5) . ?
C9 C10 1.374(4) . ?
C9 H9 0.9399 . ?
C10 C9 1.374(4) 4 ?
C10 H10 0.9842 . ?
C11 C8 1.391(4) 4 ?
C11 H11 1.0528 . ?
O1A C7A 1.325(4) . ?
O1A H1OA 1.09(4) . ?
O2A C7A 1.223(4) . ?
C1A C2A 1.392(5) . ?
C1A C6A 1.398(4) . ?
C1A C7A 1.480(5) . ?
C2A C3A 1.379(5) . ?
C2A H2A 0.9070 . ?
C3A C4A 1.384(5) . ?
C3A H3A 0.9897 . ?
C4A C5A 1.383(5) . ?
C4A O3A 1.386(4) . ?
C5A C6A 1.384(5) . ?
C5A H5A 0.9882 . ?
C6A H6A 1.0139 . ?
O3A C4A 1.386(4) 2_645 ?
