#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/62/2206221.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2206221
loop_
_publ_author_name
'Yong-Ru Liu'
'Xiang-Ping Li'
'Jing-An Zhang'
'Cheng-Yong Su'
_publ_section_title
;
 N,N'-Bis(4-pyridylmethylene)naphthalene-1,5-diamine
;
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2089
_journal_page_last               o2090
_journal_paper_doi               10.1107/S1600536805017940
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C22 H16 N4'
_chemical_formula_moiety         'C22 H16 N4'
_chemical_formula_sum            'C22 H16 N4'
_chemical_formula_weight         336.39
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                102.895(2)
_cell_angle_beta                 102.286(2)
_cell_angle_gamma                102.822(2)
_cell_formula_units_Z            2
_cell_length_a                   7.6684(7)
_cell_length_b                   10.2831(9)
_cell_length_c                   11.6172(10)
_cell_measurement_reflns_used    2932
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      24.99
_cell_measurement_theta_min      2.834
_cell_volume                     836.89(13)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        SAINT-Plus
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART APEX CCD diffractometer'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6742
_diffrn_reflns_theta_full        25.04
_diffrn_reflns_theta_max         25.04
_diffrn_reflns_theta_min         1.87
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.9903
_exptl_absorpt_correction_T_min  0.9723
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            green--brown
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.172
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    refU
_refine_ls_matrix_type           full
_refine_ls_number_parameters     251
_refine_ls_number_reflns         2957
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_gt           0.0438
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0491P)²+0.1827P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.108
_reflns_number_gt                2357
_reflns_number_total             2957
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            is6089.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               2206221
_cod_database_fobs_code          2206221
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
C1 0.1671(3) -0.04261(19) 0.35757(16) 0.0359(5) Uani d . 1 C
H1 0.1477 -0.1296 0.2998 0.036(5) Uiso calc R 1 H
C2 0.2478(2) -0.02822(18) 0.47912(15) 0.0318(4) Uani d . 1 C
H2 0.2847 -0.1025 0.5037 0.039(5) Uiso calc R 1 H
C3 0.2741(2) 0.09733(17) 0.56506(15) 0.0262(4) Uani d . 1 C
C4 0.2165(2) 0.20089(18) 0.52301(16) 0.0309(4) Uani d . 1 C
H4 0.2301 0.2878 0.579 0.035(5) Uiso calc R 1 H
C5 0.1391(2) 0.17648(19) 0.39884(16) 0.0341(4) Uani d . 1 C
H5 0.1015 0.249 0.3715 0.040(5) Uiso calc R 1 H
C6 0.3610(2) 0.12424(18) 0.69684(15) 0.0280(4) Uani d . 1 C
H6 0.373 0.2118 0.7512 0.031(5) Uiso calc R 1 H
C7 0.5126(2) 0.07344(18) 0.86750(14) 0.0277(4) Uani d . 1 C
C8 0.6641(2) 0.18823(19) 0.92185(16) 0.0313(4) Uani d . 1 C
H8 0.7037 0.248 0.875 0.035(5) Uiso calc R 1 H
C9 0.7608(2) 0.21794(19) 1.04607(15) 0.0312(4) Uani d . 1 C
H9 0.8661 0.2971 1.0822 0.030(5) Uiso calc R 1 H
C10 0.7056(2) 0.13482(18) 1.11511(15) 0.0290(4) Uani d . 1 C
H10 0.7726 0.1562 1.199 0.023(4) Uiso calc R 1 H
C11 0.5486(2) 0.01620(17) 1.06294(14) 0.0260(4) Uani d . 1 C
C12 0.7575(3) 0.5816(2) 1.01613(16) 0.0390(5) Uani d . 1 C
H12 0.7559 0.5015 1.0442 0.053(6) Uiso calc R 1 H
C13 0.6407(3) 0.56464(19) 0.90322(16) 0.0357(4) Uani d . 1 C
H13 0.5599 0.4755 0.8561 0.048(6) Uiso calc R 1 H
C14 0.6418(2) 0.67906(18) 0.85863(15) 0.0268(4) Uani d . 1 C
C15 0.7648(2) 0.80512(18) 0.93130(15) 0.0288(4) Uani d . 1 C
H15 0.7742 0.8857 0.9032 0.026(5) Uiso calc R 1 H
C16 0.8742(2) 0.81266(19) 1.04537(16) 0.0317(4) Uani d . 1 C
H16 0.9545 0.9008 1.0953 0.033(5) Uiso calc R 1 H
C17 0.5113(2) 0.67066(18) 0.74248(15) 0.0282(4) Uani d . 1 C
H17 0.5253 0.7487 0.7108 0.027(5) Uiso calc R 1 H
C18 0.2578(2) 0.55852(17) 0.57273(15) 0.0264(4) Uani d . 1 C
C19 0.3207(2) 0.59687(18) 0.47999(16) 0.0310(4) Uani d . 1 C
H19 0.4507 0.6304 0.4908 0.035(5) Uiso calc R 1 H
C20 0.1948(2) 0.58704(19) 0.36893(16) 0.0324(4) Uani d . 1 C
H20 0.2407 0.6149 0.3058 0.031(5) Uiso calc R 1 H
C21 0.0077(2) 0.53810(17) 0.35062(15) 0.0292(4) Uani d . 1 C
H21 -0.0757 0.5328 0.2753 0.023(4) Uiso calc R 1 H
C22 -0.0627(2) 0.49515(17) 0.44361(14) 0.0254(4) Uani d . 1 C
N1 0.1141(2) 0.05685(16) 0.31504(13) 0.0355(4) Uani d . 1 N
N2 0.4206(2) 0.03490(15) 0.74067(12) 0.0298(4) Uani d . 1 N
N3 0.8731(2) 0.70300(16) 1.08929(13) 0.0370(4) Uani d . 1 N
N4 0.37974(19) 0.56039(14) 0.68375(12) 0.0285(3) Uani d . 1 N
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 0 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
N1 C1 C2 . . 124.66(17)
N1 C1 H1 . . 117.7
C2 C1 H1 . . 117.7
C1 C2 C3 . . 118.44(17)
C1 C2 H2 . . 120.8
C3 C2 H2 . . 120.8
C4 C3 C2 . . 117.75(15)
C4 C3 C6 . . 119.39(15)
C2 C3 C6 . . 122.85(15)
C5 C4 C3 . . 119.25(16)
C5 C4 H4 . . 120.4
C3 C4 H4 . . 120.4
N1 C5 C4 . . 123.72(17)
N1 C5 H5 . . 118.1
C4 C5 H5 . . 118.1
N2 C6 C3 . . 122.42(15)
N2 C6 H6 . . 118.8
C3 C6 H6 . . 118.8
C8 C7 N2 . . 121.94(15)
C8 C7 C11 . 2_657 120.14(15)
N2 C7 C11 . 2_657 117.78(15)
C7 C8 C9 . . 120.55(17)
C7 C8 H8 . . 119.7
C9 C8 H8 . . 119.7
C10 C9 C8 . . 120.77(17)
C10 C9 H9 . . 119.6
C8 C9 H9 . . 119.6
C9 C10 C11 . . 120.48(15)
C9 C10 H10 . . 119.8
C11 C10 H10 . . 119.8
C10 C11 C11 . 2_657 119.3(2)
C10 C11 C7 . 2_657 121.94(14)
C11 C11 C7 2_657 2_657 118.7(2)
N3 C12 C13 . . 124.49(18)
N3 C12 H12 . . 117.8
C13 C12 H12 . . 117.8
C12 C13 C14 . . 119.23(17)
C12 C13 H13 . . 120.4
C14 C13 H13 . . 120.4
C15 C14 C13 . . 117.24(15)
C15 C14 C17 . . 120.48(16)
C13 C14 C17 . . 122.19(16)
C14 C15 C16 . . 119.34(17)
C14 C15 H15 . . 120.3
C16 C15 H15 . . 120.3
N3 C16 C15 . . 123.74(17)
N3 C16 H16 . . 118.1
C15 C16 H16 . . 118.1
N4 C17 C14 . . 121.07(16)
N4 C17 H17 . . 119.5
C14 C17 H17 . . 119.5
C19 C18 N4 . . 122.49(15)
C19 C18 C22 . 2_566 120.17(15)
N4 C18 C22 . 2_566 117.19(15)
C18 C19 C20 . . 120.62(16)
C18 C19 H19 . . 119.7
C20 C19 H19 . . 119.7
C21 C20 C19 . . 120.86(17)
C21 C20 H20 . . 119.6
C19 C20 H20 . . 119.6
C20 C21 C22 . . 120.19(15)
C20 C21 H21 . . 119.9
C22 C21 H21 . . 119.9
C21 C22 C22 . 2_566 119.60(19)
C21 C22 C18 . 2_566 121.86(14)
C22 C22 C18 2_566 2_566 118.54(19)
C5 N1 C1 . . 116.15(15)
C6 N2 C7 . . 118.28(14)
C12 N3 C16 . . 115.92(15)
C17 N4 C18 . . 118.59(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 N1 . 1.334(2)
C1 C2 . 1.376(2)
C1 H1 . 0.95
C2 C3 . 1.388(2)
C2 H2 . 0.95
C3 C4 . 1.385(2)
C3 C6 . 1.469(2)
C4 C5 . 1.380(2)
C4 H4 . 0.95
C5 N1 . 1.334(2)
C5 H5 . 0.95
C6 N2 . 1.268(2)
C6 H6 . 0.95
C7 C8 . 1.374(2)
C7 N2 . 1.414(2)
C7 C11 2_657 1.423(2)
C8 C9 . 1.405(2)
C8 H8 . 0.95
C9 C10 . 1.358(2)
C9 H9 . 0.95
C10 C11 . 1.419(2)
C10 H10 . 0.95
C11 C11 2_657 1.419(3)
C11 C7 2_657 1.423(2)
C12 N3 . 1.335(2)
C12 C13 . 1.372(2)
C12 H12 . 0.95
C13 C14 . 1.387(2)
C13 H13 . 0.95
C14 C15 . 1.383(2)
C14 C17 . 1.471(2)
C15 C16 . 1.385(2)
C15 H15 . 0.95
C16 N3 . 1.337(2)
C16 H16 . 0.95
C17 N4 . 1.274(2)
C17 H17 . 0.95
C18 C19 . 1.370(2)
C18 N4 . 1.416(2)
C18 C22 2_566 1.430(2)
C19 C20 . 1.405(2)
C19 H19 . 0.95
C20 C21 . 1.364(2)
C20 H20 . 0.95
C21 C22 . 1.417(2)
C21 H21 . 0.95
C22 C22 2_566 1.419(3)
C22 C18 2_566 1.430(2)
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_site_symmetry_1
_geom_torsion_site_symmetry_4
_geom_torsion
N1 C1 C2 C3 . . 1.1(3)
C1 C2 C3 C4 . . 0.2(3)
C1 C2 C3 C6 . . -179.22(16)
C2 C3 C4 C5 . . -1.1(3)
C6 C3 C4 C5 . . 178.42(16)
C3 C4 C5 N1 . . 0.6(3)
C4 C3 C6 N2 . . -178.32(16)
C2 C3 C6 N2 . . 1.1(3)
N2 C7 C8 C9 . . -175.25(15)
C11 C7 C8 C9 2_657 . 0.4(3)
C7 C8 C9 C10 . . -0.7(3)
C8 C9 C10 C11 . . -0.1(3)
C9 C10 C11 C11 . 2_657 1.1(3)
C9 C10 C11 C7 . 2_657 179.73(16)
N3 C12 C13 C14 . . 1.1(3)
C12 C13 C14 C15 . . 0.9(3)
C12 C13 C14 C17 . . -175.59(17)
C13 C14 C15 C16 . . -2.5(2)
C17 C14 C15 C16 . . 174.09(15)
C14 C15 C16 N3 . . 2.3(3)
C15 C14 C17 N4 . . -169.68(16)
C13 C14 C17 N4 . . 6.8(3)
N4 C18 C19 C20 . . 176.89(16)
C22 C18 C19 C20 2_566 . 1.4(3)
C18 C19 C20 C21 . . -0.6(3)
C19 C20 C21 C22 . . -0.5(3)
C20 C21 C22 C22 . 2_566 0.7(3)
C20 C21 C22 C18 . 2_566 -179.13(16)
C4 C5 N1 C1 . . 0.6(3)
C2 C1 N1 C5 . . -1.6(3)
C3 C6 N2 C7 . . 176.10(15)
C8 C7 N2 C6 . . -55.2(2)
C11 C7 N2 C6 2_657 . 129.06(17)
C13 C12 N3 C16 . . -1.4(3)
C15 C16 N3 C12 . . -0.3(3)
C14 C17 N4 C18 . . 179.71(15)
C19 C18 N4 C17 . . 51.1(2)
C22 C18 N4 C17 2_566 . -133.30(16)
