#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/97/2219777.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_2219777
loop_
_publ_author_name
'Tabatabaee, Masoumeh'
'Hakimi, Fatemeh'
'Roshani, Mina'
'Mirjalili, Mohammad'
'Kavasi, Hamid Reza'
_publ_section_title
;
 1-(2-Pyridyl)-N,N'-dipyrimidin-2-ylmethanediamine
;
_journal_coeditor_code           BQ2098
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2112
_journal_paper_doi               10.1107/S1600536808032583
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C14 H13 N7'
_chemical_formula_moiety         'C14 H13 N7'
_chemical_formula_sum            'C14 H13 N7'
_chemical_formula_weight         279.31
_chemical_name_systematic
;
1-(2-Pyridyl)-N,N'-dipyrimidin-2-ylmethanediamine
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 97.521(17)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.5781(19)
_cell_length_b                   9.3543(16)
_cell_length_c                   15.975(4)
_cell_measurement_reflns_used    2000
_cell_measurement_temperature    296
_cell_measurement_theta_max      26.77
_cell_measurement_theta_min      2.35
_cell_volume                     1419.0(5)
_computing_cell_refinement       'X-AREA (Stoe & Cie, 2005)'
_computing_data_collection       'X-AREA (Stoe & Cie, 2005)'
_computing_data_reduction        'X-RED32 (Stoe & Cie, 2005)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Stoe IPDS-II'
_diffrn_measurement_method       'rotation method'
_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  0.0322
_diffrn_reflns_av_sigmaI/netI    0.0203
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12281
_diffrn_reflns_theta_full        26.77
_diffrn_reflns_theta_max         26.77
_diffrn_reflns_theta_min         2.35
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_correction_T_min  0.970
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
'shape of crystal determined optically (Program? reference?)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.147
_refine_diff_density_min         -0.164
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         2997
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.124
_refine_ls_R_factor_all          0.0726
_refine_ls_R_factor_gt           0.0576
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0555P)²+0.3988P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1325
_refine_ls_wR_factor_ref         0.1404
_reflns_number_gt                2443
_reflns_number_total             2997
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bq2098.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2219777
_cod_database_fobs_code          2219777
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_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_occupancy
C C1 0.9822(4) 0.8397(4) 0.2536(3) 0.1170(12) Uani d 1
H H1 1.065(4) 0.909(5) 0.265(3) 0.172(17) Uiso d 1
C C2 0.9364(4) 0.7672(5) 0.3161(2) 0.1087(12) Uani d 1
H H2 0.973(4) 0.786(4) 0.372(3) 0.149(14) Uiso d 1
C C3 0.8303(4) 0.6738(5) 0.2982(2) 0.1054(12) Uani d 1
H H3 0.783(4) 0.619(4) 0.328(3) 0.141(14) Uiso d 1
C C4 0.7696(3) 0.6561(3) 0.21369(16) 0.0746(7) Uani d 1
H H4 0.702(3) 0.604(3) 0.2000(16) 0.074(8) Uiso d 1
C C5 0.82060(18) 0.7345(2) 0.15391(11) 0.0488(4) Uani d 1
C C6 0.76338(17) 0.7253(2) 0.06118(11) 0.0458(4) Uani d 1
H H6 0.7549(19) 0.821(2) 0.0380(12) 0.048(5) Uiso d 1
C C7 0.87637(17) 0.6815(2) -0.06540(11) 0.0464(4) Uani d 1
C C8 0.8208(3) 0.8159(3) -0.18238(15) 0.0816(8) Uani d 1
H H8 0.753(3) 0.896(3) -0.2127(17) 0.098(8) Uiso d 1
C C9 0.9149(3) 0.7437(3) -0.22277(16) 0.0859(8) Uani d 1
H H9 0.928(3) 0.768(3) -0.2817(19) 0.106(9) Uiso d 1
C C10 0.9855(3) 0.6351(3) -0.17964(14) 0.0745(7) Uani d 1
H H10 1.054(3) 0.577(3) -0.2047(16) 0.086(7) Uiso d 1
C C11 0.50462(17) 0.72192(19) 0.05133(10) 0.0441(4) Uani d 1
C C12 0.3865(2) 0.9233(2) 0.07540(14) 0.0599(5) Uani d 1
H H12 0.394(2) 1.026(3) 0.0921(14) 0.074(7) Uiso d 1
C C13 0.2605(2) 0.8541(3) 0.05806(16) 0.0698(6) Uani d 1
H H13 0.170(3) 0.897(3) 0.0602(16) 0.091(8) Uiso d 1
C C14 0.2664(2) 0.7119(3) 0.03806(16) 0.0681(6) Uani d 1
H H14 0.180(3) 0.652(3) 0.0280(15) 0.078(7) Uiso d 1
N N1 0.9275(2) 0.8262(3) 0.17169(15) 0.0913(7) Uani d 1
N N2 0.86343(15) 0.65215(18) 0.01597(9) 0.0504(4) Uani d 1
H H2B 0.915(2) 0.583(2) 0.0422(13) 0.058(6) Uiso d 1
N N3 0.7991(2) 0.7869(2) -0.10338(11) 0.0681(5) Uani d 1
N N4 0.96897(16) 0.59970(18) -0.10065(10) 0.0565(4) Uani d 1
N N5 0.62782(15) 0.65417(19) 0.04528(11) 0.0523(4) Uani d 1
H H5B 0.623(2) 0.575(2) 0.0285(13) 0.055(6) Uiso d 1
N N6 0.51088(15) 0.85980(16) 0.07449(10) 0.0505(4) Uani d 1
N N7 0.38702(15) 0.64257(18) 0.03335(11) 0.0569(4) Uani d 1
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
C2 C1 N1 123.8(4)
C2 C1 H1 121(2)
N1 C1 H1 115(2)
C1 C2 C3 119.2(3)
C1 C2 H2 120(3)
C3 C2 H2 120(2)
C2 C3 C4 119.1(3)
C2 C3 H3 135(3)
C4 C3 H3 106(3)
C5 C4 C3 118.3(3)
C5 C4 H4 118.9(18)
C3 C4 H4 122.7(18)
N1 C5 C4 122.5(2)
N1 C5 C6 114.40(18)
C4 C5 C6 123.1(2)
N2 C6 N5 109.37(15)
N2 C6 C5 109.70(14)
N5 C6 C5 113.47(15)
N2 C6 H6 105.9(11)
N5 C6 H6 109.2(11)
C5 C6 H6 108.9(11)
N3 C7 N4 125.93(16)
N3 C7 N2 118.29(15)
N4 C7 N2 115.78(16)
N3 C8 C9 123.0(2)
N3 C8 H8 114.3(15)
C9 C8 H8 122.5(15)
C8 C9 C10 116.7(2)
C8 C9 H9 120.8(17)
C10 C9 H9 122.4(17)
N4 C10 C9 123.6(2)
N4 C10 H10 114.7(15)
C9 C10 H10 121.8(15)
N6 C11 N7 126.46(15)
N6 C11 N5 117.52(16)
N7 C11 N5 116.02(16)
N6 C12 C13 123.62(19)
N6 C12 H12 113.6(13)
C13 C12 H12 122.7(13)
C12 C13 C14 116.41(18)
C12 C13 H13 124.8(16)
C14 C13 H13 118.7(16)
N7 C14 C13 123.1(2)
N7 C14 H14 115.2(14)
C13 C14 H14 121.6(14)
C5 N1 C1 117.0(3)
C7 N2 C6 122.37(15)
C7 N2 H2B 119.2(13)
C6 N2 H2B 118.4(13)
C7 N3 C8 115.86(17)
C10 N4 C7 114.85(17)
C11 N5 C6 122.74(16)
C11 N5 H5B 117.0(15)
C6 N5 H5B 120.0(15)
C12 N6 C11 115.09(17)
C14 N7 C11 115.17(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.327(6)
C1 N1 1.350(4)
C1 H1 1.03(4)
C2 C3 1.343(6)
C2 H2 0.93(4)
C3 C4 1.408(4)
C3 H3 0.87(4)
C4 C5 1.346(3)
C4 H4 0.82(2)
C5 N1 1.338(3)
C5 C6 1.513(3)
C6 N2 1.446(2)
C6 N5 1.452(2)
C6 H6 0.97(2)
C7 N3 1.331(2)
C7 N4 1.349(2)
C7 N2 1.350(2)
C8 N3 1.334(3)
C8 C9 1.355(3)
C8 H8 1.07(3)
C9 C10 1.357(4)
C9 H9 0.99(3)
C10 N4 1.334(3)
C10 H10 0.98(3)
C11 N6 1.341(2)
C11 N7 1.348(2)
C11 N5 1.354(2)
C12 N6 1.333(2)
C12 C13 1.366(3)
C12 H12 1.00(2)
C13 C14 1.371(3)
C13 H13 0.96(3)
C14 N7 1.335(2)
C14 H14 1.00(2)
N2 H2B 0.89(2)
N5 H5B 0.79(2)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N2 H2B N4 3_765 0.885(19) 2.181(19) 3.064(2) 175.3(19) yes
N5 H5B N7 3_665 0.787(19) 2.259(19) 3.042(3) 174(2) yes
C4 H4 N5 . 0.82(3) 2.53(3) 2.851(3) 105(2) yes
C6 H6 N3 . 0.968(19) 2.373(19) 2.756(3) 102.9(13) yes
C12 H12 N3 3_675 1.00(3) 2.57(2) 3.304(3) 130.4(15) yes
C9 H9 Cg1 4_675 0.99(3) 2.62(3) 3.532(3) 154(3) yes
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
N1 C1 C2 C3 0.4(6)
C1 C2 C3 C4 -0.5(5)
C2 C3 C4 C5 -0.3(5)
C3 C4 C5 N1 1.1(4)
C3 C4 C5 C6 -179.6(2)
N1 C5 C6 N2 71.8(2)
C4 C5 C6 N2 -107.6(2)
N1 C5 C6 N5 -165.58(18)
C4 C5 C6 N5 15.0(3)
N3 C8 C9 C10 1.8(5)
C8 C9 C10 N4 -1.6(5)
N6 C12 C13 C14 -0.7(4)
C12 C13 C14 N7 -1.5(4)
C4 C5 N1 C1 -1.1(4)
C6 C5 N1 C1 179.5(3)
C2 C1 N1 C5 0.4(5)
N3 C7 N2 C6 3.6(3)
N4 C7 N2 C6 -176.73(17)
N5 C6 N2 C7 85.7(2)
C5 C6 N2 C7 -149.27(18)
N4 C7 N3 C8 -2.7(3)
N2 C7 N3 C8 176.9(2)
C9 C8 N3 C7 0.2(4)
C9 C10 N4 C7 -0.6(4)
N3 C7 N4 C10 2.9(3)
N2 C7 N4 C10 -176.74(19)
N6 C11 N5 C6 -1.2(3)
N7 C11 N5 C6 178.94(16)
N2 C6 N5 C11 -154.94(16)
C5 C6 N5 C11 82.2(2)
C13 C12 N6 C11 2.9(3)
N7 C11 N6 C12 -3.3(3)
N5 C11 N6 C12 176.80(17)
C13 C14 N7 C11 1.2(3)
N6 C11 N7 C14 1.4(3)
N5 C11 N7 C14 -178.76(18)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24740925
