#------------------------------------------------------------------------------
#$Date: 2016-03-26 00:07:36 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180061 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/07/7050746.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_7050746
loop_
_publ_author_name
'Bensemann, Igor'
'Gdaniec, Maria'
'Połoński, Tadeusz'
_publ_section_title
;
 Supramolecular structures formed by 2-aminopyridine derivatives.
;
_journal_issue                   4
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              448
_journal_paper_doi               10.1039/b108861k
_journal_volume                  26
_journal_year                    2002
_chemical_formula_sum            'C20 H16 N4'
_chemical_formula_weight         312.37
_chemical_melting_point          259.0(10)
_chemical_name_systematic
; 
N,N'-Bis(2-pyridyl)-1,5-diaminonaphthalene  
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                100.62(3)
_cell_angle_beta                 101.57(3)
_cell_angle_gamma                114.20(3)
_cell_formula_units_Z            2
_cell_length_a                   8.118(2)
_cell_length_b                   9.361(2)
_cell_length_c                   11.803(2)
_cell_measurement_reflns_used    2450
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30
_cell_measurement_theta_min      2
_cell_volume                     765.0(4)
_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      100(2)
_diffrn_measurement_device_type  'KumaCCD 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  0.0347
_diffrn_reflns_av_sigmaI/netI    0.0617
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5718
_diffrn_reflns_theta_max         24.40
_diffrn_reflns_theta_min         3.79
_diffrn_standards_decay_%        <1
_diffrn_standards_interval_count 50
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'light brown'
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.460
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.962
_refine_ls_hydrogen_treatment    'riding model'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2499
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.962
_refine_ls_R_factor_all          0.1108
_refine_ls_R_factor_gt           0.0631
_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)+(0.1240P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1689
_refine_ls_wR_factor_ref         0.2022
_reflns_number_gt                1387
_reflns_number_total             2499
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b108861k.txt
_cod_data_source_block           4
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '258-260' was changed to '259.0(10)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1569 2011-02-09 13:29:24Z adriana 
;
_cod_original_cell_volume        765.0(3)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7050746
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
N1A N 0.2993(4) 0.5212(3) -0.0782(2) 0.0439(7) Uani 1 1 d . . .
C2A C 0.4190(5) 0.6662(4) -0.0825(3) 0.0448(9) Uani 1 1 d . . .
C3A C 0.3578(5) 0.7740(4) -0.1197(3) 0.0523(10) Uani 1 1 d . . .
H3A H 0.4484 0.8807 -0.1178 0.063 Uiso 1 1 d R . .
C4A C 0.1682(5) 0.7260(5) -0.1584(3) 0.0568(10) Uani 1 1 d . . .
H4A H 0.1241 0.7978 -0.1865 0.068 Uiso 1 1 d R . .
C5A C 0.0398(5) 0.5739(5) -0.1580(3) 0.0569(10) Uani 1 1 d . . .
H5A H -0.0945 0.5373 -0.1853 0.068 Uiso 1 1 d R . .
C6A C 0.1107(5) 0.4777(5) -0.1168(3) 0.0555(10) Uani 1 1 d . . .
H6A H 0.0223 0.3724 -0.1150 0.067 Uiso 1 1 d R . .
N7A N 0.6089(4) 0.7075(3) -0.0437(3) 0.0515(8) Uani 1 1 d . . .
H7A H 0.6442 0.6549 0.0051 0.062 Uiso 1 1 d R . .
C8A C 0.7539(5) 0.8282(4) -0.0760(3) 0.0463(9) Uani 1 1 d . . .
C9A C 0.7293(5) 0.8374(4) -0.1906(3) 0.0486(9) Uani 1 1 d . . .
H9A H 0.6126 0.7612 -0.2530 0.058 Uiso 1 1 d R . .
C10A C 0.9273(4) 0.9388(4) 0.0142(3) 0.0419(8) Uani 1 1 d . . .
C11A C 0.9600(5) 0.9350(4) 0.1378(3) 0.0481(9) Uani 1 1 d . . .
H11A H 0.8633 0.8559 0.1609 0.058 Uiso 1 1 d R . .
C12A C 1.1318(5) 1.0460(4) 0.2223(3) 0.0487(9) Uani 1 1 d . . .
H12A H 1.1559 1.0452 0.3051 0.058 Uiso 1 1 d R . .
N1B N 0.7733(4) 0.8607(3) 0.3941(2) 0.0414(7) Uani 1 1 d . . .
C2B C 0.7350(4) 0.9868(4) 0.3918(3) 0.0391(8) Uani 1 1 d . . .
C3B C 0.5756(5) 0.9695(4) 0.3083(3) 0.0459(9) Uani 1 1 d . . .
H3B H 0.5499 1.0610 0.3093 0.055 Uiso 1 1 d R . .
C4B C 0.4559(5) 0.8195(4) 0.2242(3) 0.0480(9) Uani 1 1 d . . .
H4B H 0.3447 0.8050 0.1659 0.058 Uiso 1 1 d R . .
C5B C 0.4956(5) 0.6891(4) 0.2236(3) 0.0472(9) Uani 1 1 d . . .
H5B H 0.4143 0.5835 0.1650 0.057 Uiso 1 1 d R . .
C6B C 0.6546(5) 0.7168(4) 0.3099(3) 0.0451(9) Uani 1 1 d . . .
H6B H 0.6827 0.6267 0.3098 0.054 Uiso 1 1 d R . .
N7B N 0.8658(4) 1.1336(3) 0.4766(2) 0.0458(8) Uani 1 1 d . . .
H7B H 0.9680 1.1354 0.5250 0.055 Uiso 1 1 d R . .
C8B C 0.8531(4) 1.2812(4) 0.4945(3) 0.0390(8) Uani 1 1 d . . .
C9B C 0.6994(5) 1.2889(4) 0.5185(3) 0.0477(9) Uani 1 1 d . . .
H9B H 0.5968 1.1921 0.5216 0.057 Uiso 1 1 d R . .
C10B C 1.0056(4) 1.4251(4) 0.4900(3) 0.0361(8) Uani 1 1 d . . .
C11B C 1.1686(4) 1.4240(4) 0.4649(3) 0.0418(8) Uani 1 1 d . . .
H11B H 1.1776 1.3235 0.4499 0.050 Uiso 1 1 d R . .
C12B C 1.3126(5) 1.5629(4) 0.4618(3) 0.0443(9) Uani 1 1 d . . .
H12B H 1.4221 1.5601 0.4447 0.053 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'
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
C2A N1A C6A 117.0(3) . . y
N1A C2A N7A 116.1(3) . . y
N1A C2A C3A 122.2(3) . . y
N7A C2A C3A 121.6(3) . . y
C4A C3A C2A 119.1(3) . . y
C3A C4A C5A 120.0(3) . . y
C6A C5A C4A 117.4(3) . . y
C5A C6A N1A 124.2(4) . . y
C2A N7A C8A 124.5(3) . . y
C9A C8A C10A 119.3(3) . . y
C9A C8A N7A 121.8(3) . . y
C10A C8A N7A 118.9(3) . . y
C8A C9A C12A 122.1(3) . 2_775 y
C8A C10A C10A 120.4(4) . 2_775 y
C8A C10A C11A 121.5(3) . . y
C10A C10A C11A 118.1(4) 2_775 . y
C12A C11A C10A 119.1(3) . . y
C11A C12A C9A 121.0(3) . 2_775 y
C6B N1B C2B 117.4(3) . . y
N1B C2B N7B 115.1(3) . . y
N1B C2B C3B 122.0(3) . . y
N7B C2B C3B 122.8(3) . . y
C4B C3B C2B 118.9(3) . . y
C3B C4B C5B 119.8(3) . . y
C6B C5B C4B 117.4(3) . . y
N1B C6B C5B 124.5(3) . . y
C2B N7B C8B 125.5(3) . . y
C9B C8B N7B 120.8(3) . . y
C9B C8B C10B 119.8(3) . . y
N7B C8B C10B 119.4(3) . . y
C8B C9B C12B 121.0(3) . 2_786 y
C11B C10B C10B 118.4(4) . 2_786 y
C11B C10B C8B 122.1(3) . . y
C10B C10B C8B 119.5(4) 2_786 . y
C12B C11B C10B 121.1(3) . . y
C11B C12B C9B 120.3(3) . 2_786 y
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
N1A C2A 1.324(4) . y
N1A C6A 1.363(4) . y
C2A N7A 1.378(4) . y
C2A C3A 1.395(5) . y
C3A C4A 1.361(5) . y
C4A C5A 1.379(5) . y
C5A C6A 1.362(5) . y
N7A C8A 1.434(4) . y
C8A C9A 1.351(5) . y
C8A C10A 1.409(4) . y
C9A C12A 1.383(5) 2_775 y
C10A C10A 1.418(6) 2_775 y
C10A C11A 1.439(5) . y
C11A C12A 1.376(5) . y
C12A C9A 1.383(5) 2_775 y
N1B C6B 1.338(4) . y
N1B C2B 1.342(4) . y
C2B N7B 1.374(4) . y
C2B C3B 1.389(4) . y
C3B C4B 1.372(5) . y
C4B C5B 1.383(5) . y
C5B C6B 1.368(5) . y
N7B C8B 1.408(4) . y
C8B C9B 1.360(4) . y
C8B C10B 1.427(4) . y
C9B C12B 1.410(4) 2_786 y
C10B C11B 1.417(4) . y
C10B C10B 1.421(6) 2_786 y
C11B C12B 1.359(4) . y
C12B C9B 1.410(4) 2_786 y
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1A C2A N7A C8A 158.9(3) . . . . y
C3A C2A N7A C8A -23.4(5) . . . . y
C2A N7A C8A C9A -43.5(5) . . . . y
C2A N7A C8A C10A 137.2(3) . . . . y
N1B C2B N7B C8B -177.7(3) . . . . y
C3B C2B N7B C8B 3.1(5) . . . . y
C2B N7B C8B C9B 56.4(5) . . . . y
C2B N7B C8B C10B -125.0(3) . . . . y
