#------------------------------------------------------------------------------
#$Date: 2018-10-05 15:19:55 +0300 (Fri, 05 Oct 2018) $
#$Revision: 211332 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/04/7150494.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_7150494
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         'C23H20N4, 0.5(C8H6O4), C2H6O'
_chemical_formula_sum            'C29 H29 N4 O3'
_chemical_formula_weight         481.56
_chemical_melting_point          'clouds at 76C, begins to melt at 176C'
_chemical_name_systematic
; 
N,N'-bis(2-pyridyl)-4,4'-methylenebis(aminobenzene) 
1,4-benzenedicarboxylic acid ethanol 2:1:2 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                88.060(9)
_cell_angle_beta                 87.645(9)
_cell_angle_gamma                86.861(9)
_cell_formula_units_Z            2
_cell_length_a                   8.7830(11)
_cell_length_b                   10.6035(11)
_cell_length_c                   13.8087(15)
_cell_measurement_reflns_used    'not relevant with the CCD data'
_cell_measurement_temperature    294(2)
_cell_volume                     1282.4(3)
_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      294(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_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  0.0366
_diffrn_reflns_av_sigmaI/netI    0.0619
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9437
_diffrn_reflns_theta_full        24.41
_diffrn_reflns_theta_max         24.41
_diffrn_reflns_theta_min         4.08
_diffrn_standards_decay_%        <2
_diffrn_standards_interval_count 50
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             510
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.140
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.033
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     348
_refine_ls_number_reflns         4179
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.1515
_refine_ls_R_factor_gt           0.0713
_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)+(0.0887P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1562
_refine_ls_wR_factor_ref         0.1934
_reflns_number_gt                2203
_reflns_number_total             4179
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b211675h.txt
_cod_data_source_block           3tere
_cod_depositor_comments
;
The following automatic conversions were performed:

'_atom_sites_solution_hydrogens' value 'difmap,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      P-1
_cod_database_code               7150494
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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 0.5055(3) 0.5987(3) 0.3991(2) 0.0626(8) Uani 1 1 d . . .
H1N H 0.420(4) 0.670(4) 0.425(3) 0.097(12) Uiso 1 1 d . . .
C2 C 0.4653(4) 0.4962(3) 0.3526(2) 0.0574(9) Uani 1 1 d . . .
C3 C 0.5807(4) 0.4071(3) 0.3259(3) 0.0782(11) Uani 1 1 d . . .
H3 H 0.5540 0.3341 0.2925 0.099(13) Uiso 1 1 d R . .
C4 C 0.7280(5) 0.4264(4) 0.3472(3) 0.0918(13) Uani 1 1 d . . .
H4 H 0.8073 0.3641 0.3304 0.115(15) Uiso 1 1 d R . .
C5 C 0.7656(5) 0.5328(4) 0.3946(3) 0.0873(12) Uani 1 1 d . . .
H5 H 0.8687 0.5486 0.4090 0.096(12) Uiso 1 1 d R . .
C6 C 0.6502(4) 0.6172(4) 0.4187(3) 0.0763(11) Uani 1 1 d . . .
H6 H 0.6755 0.6917 0.4508 0.091(12) Uiso 1 1 d R . .
N7 N 0.3158(3) 0.4878(2) 0.3383(2) 0.0644(8) Uani 1 1 d . . .
H7 H 0.2439 0.5496 0.3655 0.074(10) Uiso 1 1 d R . .
C8 C 0.2542(4) 0.3888(3) 0.2869(3) 0.0565(9) Uani 1 1 d . . .
C9 C 0.2943(4) 0.3721(3) 0.1906(3) 0.0781(11) Uani 1 1 d . . .
H9 H 0.3648 0.4271 0.1584 0.087(11) Uiso 1 1 d R . .
C10 C 0.2326(5) 0.2781(3) 0.1412(3) 0.0790(11) Uani 1 1 d . . .
H10 H 0.2623 0.2663 0.0743 0.090(12) Uiso 1 1 d R . .
C11 C 0.1297(4) 0.1979(3) 0.1852(3) 0.0614(9) Uani 1 1 d . . .
C12 C 0.0905(4) 0.2168(3) 0.2815(3) 0.0680(10) Uani 1 1 d . . .
H12 H 0.0185 0.1622 0.3127 0.094(12) Uiso 1 1 d R . .
C13 C 0.1516(4) 0.3115(3) 0.3326(3) 0.0651(10) Uani 1 1 d . . .
H13 H 0.1225 0.3232 0.3996 0.061(10) Uiso 1 1 d R . .
C14 C 0.0639(4) 0.0954(3) 0.1298(3) 0.0830(12) Uani 1 1 d . . .
H14B H 0.0399 0.1293 0.0666 0.087(13) Uiso 1 1 d R . .
H14A H -0.0287 0.0689 0.1617 0.093(13) Uiso 1 1 d R . .
C15 C 0.1694(4) -0.0201(3) 0.1162(3) 0.0619(9) Uani 1 1 d . . .
C16 C 0.2571(6) -0.0364(4) 0.0344(3) 0.1065(15) Uani 1 1 d . . .
H16 H 0.2563 0.0290 -0.0154 0.151(19) Uiso 1 1 d R . .
C17 C 0.3535(6) -0.1433(4) 0.0209(3) 0.1073(16) Uani 1 1 d . . .
H17 H 0.4125 -0.1516 -0.0389 0.117(15) Uiso 1 1 d R . .
C18 C 0.3634(4) -0.2370(3) 0.0894(3) 0.0650(10) Uani 1 1 d . . .
C19 C 0.2771(6) -0.2221(4) 0.1726(4) 0.1088(16) Uani 1 1 d . . .
H19 H 0.2802 -0.2871 0.2227 0.128(16) Uiso 1 1 d R . .
C20 C 0.1809(6) -0.1143(4) 0.1851(4) 0.1092(16) Uani 1 1 d . . .
H20 H 0.1217 -0.1072 0.2449 0.107(14) Uiso 1 1 d R . .
N21 N 0.4562(4) -0.3497(3) 0.0725(2) 0.0789(9) Uani 1 1 d . . .
H21 H 0.4098 -0.4157 0.0403 0.138(17) Uiso 1 1 d R . .
C22 C 0.6036(4) -0.3706(3) 0.0994(3) 0.0690(10) Uani 1 1 d G . .
N23 N 0.6708(4) -0.4777(2) 0.0665(2) 0.0812(9) Uani 1 1 d G . .
C24 C 0.8168(4) -0.5005(4) 0.0876(3) 0.1032(14) Uani 1 1 d G . .
H24 H 0.8644 -0.5771 0.0630 0.112(14) Uiso 1 1 d R . .
C25 C 0.9001(6) -0.4261(5) 0.1394(4) 0.1225(18) Uani 1 1 d . . .
H25 H 1.0053 -0.4470 0.1518 0.145(19) Uiso 1 1 d R . .
C26 C 0.8271(6) -0.3157(5) 0.1738(4) 0.1140(16) Uani 1 1 d . . .
H26 H 0.8825 -0.2599 0.2109 0.119(15) Uiso 1 1 d R . .
C27 C 0.6774(5) -0.2881(4) 0.1549(3) 0.0873(12) Uani 1 1 d . . .
H27 H 0.6244 -0.2135 0.1795 0.099(13) Uiso 1 1 d R . .
C4A C 0.0848(4) 0.8922(3) 0.4714(2) 0.0556(9) Uani 1 1 d . . .
C2A C -0.0686(4) 0.9056(3) 0.4550(3) 0.0628(9) Uani 1 1 d . . .
H2A H -0.1121 0.8346 0.4274 0.071(10) Uiso 1 1 d R . .
C3A C 0.1539(4) 0.9882(3) 0.5162(3) 0.0630(9) Uani 1 1 d . . .
H3A H 0.2561 0.9802 0.5386 0.059(9) Uiso 1 1 d R . .
C1A C 0.1774(4) 0.7754(3) 0.4425(3) 0.0632(9) Uani 1 1 d . . .
O1A O 0.3213(3) 0.7793(2) 0.4491(2) 0.0876(9) Uani 1 1 d . . .
O2A O 0.1140(3) 0.6834(2) 0.4132(2) 0.0837(8) Uani 1 1 d . . .
O1E O 0.5459(4) -0.0734(3) 0.3639(3) 0.1439(14) Uani 1 1 d . . .
H1E H 0.4566 -0.1132 0.3894 0.173 Uiso 1 1 d R . .
C2E C 0.5032(7) 0.0399(5) 0.3172(6) 0.145(2) Uani 1 1 d . . .
H2EA H 0.4950 0.1059 0.3632 0.174 Uiso 1 1 d R . .
H2EB H 0.4073 0.0333 0.2873 0.174 Uiso 1 1 d R . .
C3E C 0.6198(11) 0.0701(6) 0.2459(5) 0.194(3) Uani 1 1 d . . .
H3EA H 0.5965 0.1490 0.2121 0.233 Uiso 1 1 d R . .
H3EB H 0.7150 0.0764 0.2767 0.233 Uiso 1 1 d R . .
H3EC H 0.6267 0.0034 0.2004 0.233 Uiso 1 1 d R . .
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 122.3(3) . . ?
C6 N1 H1N 116.4(18) . . ?
C2 N1 H1N 121.2(18) . . ?
N7 C2 N1 116.6(3) . . ?
N7 C2 C3 125.6(3) . . ?
N1 C2 C3 117.7(3) . . ?
C4 C3 C2 119.4(4) . . ?
C4 C3 H3 121.9 . . ?
C2 C3 H3 118.7 . . ?
C3 C4 C5 121.5(4) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.0 . . ?
C6 C5 C4 117.2(4) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 122.6 . . ?
N1 C6 C5 121.8(4) . . ?
N1 C6 H6 120.5 . . ?
C5 C6 H6 117.7 . . ?
C2 N7 C8 124.0(3) . . ?
C2 N7 H7 119.3 . . ?
C8 N7 H7 116.7 . . ?
C13 C8 C9 119.4(3) . . ?
C13 C8 N7 120.2(3) . . ?
C9 C8 N7 120.4(3) . . ?
C10 C9 C8 120.1(4) . . ?
C10 C9 H9 120.6 . . ?
C8 C9 H9 119.3 . . ?
C9 C10 C11 122.0(4) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 118.4 . . ?
C12 C11 C10 116.9(3) . . ?
C12 C11 C14 121.9(4) . . ?
C10 C11 C14 121.2(4) . . ?
C11 C12 C13 121.8(3) . . ?
C11 C12 H12 117.7 . . ?
C13 C12 H12 120.4 . . ?
C8 C13 C12 119.7(4) . . ?
C8 C13 H13 119.8 . . ?
C12 C13 H13 120.4 . . ?
C11 C14 C15 114.4(3) . . ?
C11 C14 H14B 108.1 . . ?
C15 C14 H14B 107.7 . . ?
C11 C14 H14A 110.3 . . ?
C15 C14 H14A 107.9 . . ?
H14B C14 H14A 108.2 . . ?
C16 C15 C20 116.2(4) . . ?
C16 C15 C14 121.9(4) . . ?
C20 C15 C14 121.9(4) . . ?
C15 C16 C17 122.2(4) . . ?
C15 C16 H16 119.4 . . ?
C17 C16 H16 118.3 . . ?
C18 C17 C16 121.2(4) . . ?
C18 C17 H17 119.3 . . ?
C16 C17 H17 119.5 . . ?
C17 C18 C19 117.5(4) . . ?
C17 C18 N21 120.8(4) . . ?
C19 C18 N21 121.6(4) . . ?
C18 C19 C20 120.6(4) . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 119.4 . . ?
C15 C20 C19 122.2(4) . . ?
C15 C20 H20 119.6 . . ?
C19 C20 H20 118.1 . . ?
C22 N21 C18 125.3(3) . . ?
C22 N21 H21 118.0 . . ?
C18 N21 H21 116.7 . . ?
N23 C22 N21 113.8(3) . . ?
N23 C22 C27 122.9(3) . . ?
N21 C22 C27 123.3(3) . . ?
C24 N23 C22 116.2 . . ?
N23 C24 C25 125.8(3) . . ?
N23 C24 H24 115.6 . . ?
C25 C24 H24 118.6 . . ?
C24 C25 C26 116.9(5) . . ?
C24 C25 H25 122.1 . . ?
C26 C25 H25 120.9 . . ?
C27 C26 C25 119.8(5) . . ?
C27 C26 H26 120.6 . . ?
C25 C26 H26 119.6 . . ?
C26 C27 C22 118.3(4) . . ?
C26 C27 H27 120.9 . . ?
C22 C27 H27 120.7 . . ?
C2A C4A C3A 119.1(3) . . ?
C2A C4A C1A 121.0(3) . . ?
C3A C4A C1A 119.9(3) . . ?
C4A C2A C3A 120.7(3) . 2_576 ?
C4A C2A H2A 115.8 . . ?
C3A C2A H2A 123.2 2_576 . ?
C2A C3A C4A 120.1(3) 2_576 . ?
C2A C3A H3A 115.5 2_576 . ?
C4A C3A H3A 123.6 . . ?
O2A C1A O1A 123.8(3) . . ?
O2A C1A C4A 120.3(3) . . ?
O1A C1A C4A 115.9(3) . . ?
C1A O1A H1N 119.8(14) . . ?
C2E O1E H1E 109.6 . . ?
O1E C2E C3E 108.8(6) . . ?
O1E C2E H2EA 109.4 . . ?
C3E C2E H2EA 108.0 . . ?
O1E C2E H2EB 110.1 . . ?
C3E C2E H2EB 110.6 . . ?
H2EA C2E H2EB 109.9 . . ?
C2E C3E H3EA 112.1 . . ?
C2E C3E H3EB 109.7 . . ?
H3EA C3E H3EB 108.0 . . ?
C2E C3E H3EC 107.1 . . ?
H3EA C3E H3EC 109.2 . . ?
H3EB C3E H3EC 110.8 . . ?
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 1.337(4) . ?
N1 C2 1.351(4) . ?
N1 H1N 1.09(4) . ?
C2 N7 1.344(4) . ?
C2 C3 1.394(5) . ?
C3 C4 1.366(5) . ?
C3 H3 0.9600 . ?
C4 C5 1.385(5) . ?
C4 H4 0.9601 . ?
C5 C6 1.353(5) . ?
C5 H5 0.9600 . ?
C6 H6 0.9601 . ?
N7 C8 1.430(4) . ?
N7 H7 0.9600 . ?
C8 C13 1.371(4) . ?
C8 C9 1.376(5) . ?
C9 C10 1.374(5) . ?
C9 H9 0.9600 . ?
C10 C11 1.383(5) . ?
C10 H10 0.9599 . ?
C11 C12 1.378(5) . ?
C11 C14 1.505(4) . ?
C12 C13 1.390(4) . ?
C12 H12 0.9599 . ?
C13 H13 0.9599 . ?
C14 C15 1.507(4) . ?
C14 H14B 0.9600 . ?
C14 H14A 0.9600 . ?
C15 C16 1.351(5) . ?
C15 C20 1.358(5) . ?
C16 C17 1.391(5) . ?
C16 H16 0.9600 . ?
C17 C18 1.350(5) . ?
C17 H17 0.9601 . ?
C18 C19 1.359(5) . ?
C18 N21 1.429(4) . ?
C19 C20 1.396(6) . ?
C19 H19 0.9599 . ?
C20 H20 0.9601 . ?
N21 C22 1.365(4) . ?
N21 H21 0.9600 . ?
C22 N23 1.3353 . ?
C22 C27 1.387(5) . ?
N23 C24 1.3336 . ?
C24 C25 1.346(6) . ?
C24 H24 0.9599 . ?
C25 C26 1.392(6) . ?
C25 H25 0.9599 . ?
C26 C27 1.365(6) . ?
C26 H26 0.9600 . ?
C27 H27 0.9600 . ?
C4A C2A 1.374(4) . ?
C4A C3A 1.388(4) . ?
C4A C1A 1.500(4) . ?
C2A C3A 1.379(4) 2_576 ?
C2A H2A 0.9601 . ?
C3A C2A 1.379(4) 2_576 ?
C3A H3A 0.9600 . ?
C1A O2A 1.237(4) . ?
C1A O1A 1.274(4) . ?
O1A H1N 1.45(4) . ?
O1E C2E 1.384(5) . ?
O1E H1E 0.9600 . ?
C2E C3E 1.432(8) . ?
C2E H2EA 0.9599 . ?
C2E H2EB 0.9600 . ?
C3E H3EA 0.9600 . ?
C3E H3EB 0.9600 . ?
C3E H3EC 0.9599 . ?
