#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/62/2016265.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_2016265
loop_
_publ_author_name
'Mambanda, Allen'
'Jaganyi, Deogratius'
'Munro, Orde Q.'
_publ_section_title
;
 One-dimensional C---H···N hydrogen-bonded
 polymers in flexible tetrapyridyl systems
;
_journal_coeditor_code           HJ3054
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o676
_journal_page_last               o680
_journal_paper_doi               10.1107/S0108270107049293
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C28 H32 N6'
_chemical_formula_moiety         'C28 H32 N6'
_chemical_formula_sum            'C28 H32 N6'
_chemical_formula_weight         452.6
_chemical_name_systematic
;
N,N,N',N'-tetrakis(2-pyridylmethyl)butane-1,4-diamine
;
_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                101.756(3)
_cell_angle_beta                 96.953(4)
_cell_angle_gamma                106.289(4)
_cell_formula_units_Z            1
_cell_length_a                   6.1942(3)
_cell_length_b                   9.2425(3)
_cell_length_c                   11.6798(5)
_cell_measurement_reflns_used    6130
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      33.8493
_cell_measurement_theta_min      3.5435
_cell_volume                     616.96(5)
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 2006)'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2006)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2006)'
_computing_molecular_graphics    'WinGX (Farrugia, 1999)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.839
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur2 CCD'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0198
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9960
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         34.01
_diffrn_reflns_theta_min         3.55
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_correction_T_min  0.9451
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
empirical absorption correction using spherical harmonics
(CrysAlis RED; Oxford Diffraction, 2006)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.218
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'thick plate'
_exptl_crystal_F_000             242
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.514
_refine_diff_density_min         -0.274
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         4227
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_gt           0.0451
_refine_ls_shift/su_max          0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.1013P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1385
_reflns_number_gt                3241
_reflns_number_total             4227
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hj3054.cif
_cod_data_source_block           II
_cod_database_code               2016265
_cod_database_fobs_code          2016265
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.87861(15) -0.00048(10) 0.00591(8) 0.01689(18) Uani d 1
C C2 0.73069(15) -0.01230(10) -0.11180(8) 0.01632(17) Uani d 1
C C3 0.70889(15) 0.06927(10) -0.29429(8) 0.01621(17) Uani d 1
C C4 0.77234(14) -0.05903(10) -0.37091(7) 0.01496(17) Uani d 1
C C5 1.00079(15) -0.05395(10) -0.36452(8) 0.01618(17) Uani d 1
C C6 1.05392(16) -0.16940(11) -0.44113(8) 0.01828(18) Uani d 1
C C7 0.87743(17) -0.28621(12) -0.52090(9) 0.0230(2) Uani d 1
C C8 0.65573(18) -0.28353(13) -0.52117(10) 0.0278(2) Uani d 1
C C9 0.81079(16) 0.26152(10) -0.10755(8) 0.01667(17) Uani d 1
C C10 0.95777(15) 0.39319(9) -0.14940(7) 0.01498(17) Uani d 1
C C11 1.19356(16) 0.42026(11) -0.13810(8) 0.01878(18) Uani d 1
C C12 1.32435(16) 0.54041(11) -0.17909(8) 0.02066(19) Uani d 1
C C13 1.21481(16) 0.63050(10) -0.23023(8) 0.01931(19) Uani d 1
C C14 0.98061(16) 0.59657(10) -0.23707(8) 0.01879(18) Uani d 1
N N1 0.82702(12) 0.11135(8) -0.17002(6) 0.01422(15) Uani d 1
N N2 0.60084(14) -0.17227(10) -0.44725(7) 0.02344(19) Uani d 1
N N3 0.85111(13) 0.48060(9) -0.19789(7) 0.01747(17) Uani d 1
H H1A 0.798(2) -0.0940(15) 0.0365(11) 0.024(3) Uiso d 1
H H1B 0.884(2) 0.0915(15) 0.0655(11) 0.022(3) Uiso d 1
H H2A 0.7176(19) -0.1124(13) -0.1645(10) 0.015(3) Uiso d 1
H H2B 0.570(2) -0.0168(15) -0.0987(11) 0.024(3) Uiso d 1
H H3A 0.7539(19) 0.1644(14) -0.3292(10) 0.021(3) Uiso d 1
H H3B 0.535(2) 0.0357(14) -0.3021(11) 0.023(3) Uiso d 1
H H5 1.119(2) 0.0295(16) -0.3118(12) 0.028(3) Uiso d 1
H H6 1.214(2) -0.1659(14) -0.4404(11) 0.022(3) Uiso d 1
H H7 0.906(2) -0.3698(16) -0.5767(12) 0.029(3) Uiso d 1
H H8 0.526(2) -0.3655(17) -0.5761(12) 0.031(3) Uiso d 1
H H9A 0.871(2) 0.2793(15) -0.0191(12) 0.024(3) Uiso d 1
H H9B 0.647(2) 0.2652(14) -0.1204(10) 0.018(3) Uiso d 1
H H11 1.270(2) 0.3527(14) -0.1017(12) 0.023(3) Uiso d 1
H H12 1.490(2) 0.5575(16) -0.1701(12) 0.032(3) Uiso d 1
H H13 1.301(2) 0.7165(15) -0.2597(11) 0.026(3) Uiso d 1
H H14 0.899(2) 0.6610(15) -0.2710(11) 0.026(3) Uiso 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 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
_geom_angle_publ_flag
C2 C1 C1 . 2_755 112.98(9) ?
C2 C1 H1A . . 106.9(7) ?
C1 C1 H1A 2_755 . 110.2(7) ?
C2 C1 H1B . . 110.7(7) ?
C1 C1 H1B 2_755 . 109.7(8) ?
H1A C1 H1B . . 106.0(10) ?
N1 C2 C1 . . 113.85(7) ?
N1 C2 H2A . . 108.4(7) ?
C1 C2 H2A . . 106.7(6) ?
N1 C2 H2B . . 111.8(7) ?
C1 C2 H2B . . 109.1(7) ?
H2A C2 H2B . . 106.6(10) ?
N1 C3 C4 . . 112.34(7) ?
N1 C3 H3A . . 109.3(6) ?
C4 C3 H3A . . 107.3(7) ?
N1 C3 H3B . . 112.2(7) ?
C4 C3 H3B . . 108.5(7) ?
H3A C3 H3B . . 107.0(9) ?
N2 C4 C5 . . 122.54(8) ?
N2 C4 C3 . . 116.67(8) ?
C5 C4 C3 . . 120.74(8) ?
C6 C5 C4 . . 119.15(8) ?
C6 C5 H5 . . 119.9(8) ?
C4 C5 H5 . . 120.8(8) ?
C7 C6 C5 . . 118.58(8) ?
C7 C6 H6 . . 120.9(7) ?
C5 C6 H6 . . 120.5(7) ?
C8 C7 C6 . . 118.77(9) ?
C8 C7 H7 . . 119.6(8) ?
C6 C7 H7 . . 121.6(8) ?
N2 C8 C7 . . 123.47(9) ?
N2 C8 H8 . . 115.6(8) ?
C7 C8 H8 . . 121.0(8) ?
N1 C9 C10 . . 110.95(7) ?
N1 C9 H9A . . 108.2(7) ?
C10 C9 H9A . . 107.7(7) ?
N1 C9 H9B . . 112.1(7) ?
C10 C9 H9B . . 108.0(7) ?
H9A C9 H9B . . 109.8(10) ?
N3 C10 C11 . . 122.38(8) ?
N3 C10 C9 . . 117.05(8) ?
C11 C10 C9 . . 120.57(7) ?
C12 C11 C10 . . 119.46(8) ?
C12 C11 H11 . . 119.6(7) ?
C10 C11 H11 . . 121.0(7) ?
C11 C12 C13 . . 118.45(9) ?
C11 C12 H12 . . 118.1(8) ?
C13 C12 H12 . . 123.5(8) ?
C14 C13 C12 . . 118.36(8) ?
C14 C13 H13 . . 120.8(7) ?
C12 C13 H13 . . 120.9(7) ?
N3 C14 C13 . . 124.01(8) ?
N3 C14 H14 . . 116.0(7) ?
C13 C14 H14 . . 120.0(7) ?
C3 N1 C9 . . 110.03(7) y
C3 N1 C2 . . 109.96(7) y
C9 N1 C2 . . 111.55(7) y
C4 N2 C8 . . 117.49(8) y
C10 N3 C14 . . 117.33(8) y
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.5229(12) ?
C1 C1 2_755 1.5244(17) ?
C1 H1A . 1.026(13) ?
C1 H1B . 0.972(13) ?
C2 N1 . 1.4687(10) y
C2 H2A . 0.977(12) ?
C2 H2B . 1.015(12) ?
C3 N1 . 1.4651(11) y
C3 C4 . 1.5085(12) ?
C3 H3A . 1.026(12) ?
C3 H3B . 1.018(12) ?
C4 N2 . 1.3363(12) y
C4 C5 . 1.3950(12) ?
C5 C6 . 1.3881(12) ?
C5 H5 . 0.945(14) ?
C6 C7 . 1.3821(14) ?
C6 H6 . 0.984(12) ?
C7 C8 . 1.3801(15) ?
C7 H7 . 0.977(14) ?
C8 N2 . 1.3506(13) y
C8 H8 . 0.984(15) ?
C9 N1 . 1.4671(11) y
C9 C10 . 1.5091(11) ?
C9 H9A . 1.018(13) ?
C9 H9B . 1.019(12) ?
C10 N3 . 1.3435(11) y
C10 C11 . 1.3957(12) ?
C11 C12 . 1.3872(13) ?
C11 H11 . 1.009(12) ?
C12 C13 . 1.3899(13) ?
C12 H12 . 0.983(13) ?
C13 C14 . 1.3841(13) ?
C13 H13 . 0.976(13) ?
C14 N3 . 1.3447(11) y
C14 H14 . 0.992(13) ?
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
C6 H6 N2 1_655 0.980(10) 2.420(10) 3.4050(10) 177.0(10)
C12 H12 N3 1_655 0.980(10) 2.57(2) 3.4840(10) 155.0(10)
C7 H7 Cg2 2_576 0.980(10) 2.79(2) 3.6630(10) 149.0(10)
C9 H9A Cg2 2_565 1.020(10) 2.72(2) 3.5450(10) 139.0(10)
C14 H14 Cg1 1_545 0.990(10) 2.86(2) 3.7560(10) 151.0(10)
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
_geom_torsion_publ_flag
C1 C1 C2 N1 2_755 -56.58(12) y
N1 C3 C4 N2 . 136.20(8) y
N1 C3 C4 C5 . -46.42(10) y
N2 C4 C5 C6 . 0.85(13) ?
C3 C4 C5 C6 . -176.36(8) ?
C4 C5 C6 C7 . -0.34(12) ?
C5 C6 C7 C8 . -0.06(14) ?
C6 C7 C8 N2 . 0.00(17) ?
N1 C9 C10 N3 . 120.23(8) y
N1 C9 C10 C11 . -59.36(10) y
N3 C10 C11 C12 . -0.65(13) ?
C9 C10 C11 C12 . 178.91(8) ?
C10 C11 C12 C13 . 0.11(14) ?
C11 C12 C13 C14 . 0.42(13) ?
C12 C13 C14 N3 . -0.48(14) ?
C4 C3 N1 C9 . 164.47(7) ?
C4 C3 N1 C2 . -72.29(9) ?
C10 C9 N1 C3 . -71.12(9) ?
C10 C9 N1 C2 . 166.57(7) ?
C1 C2 N1 C3 . 165.15(7) ?
C1 C2 N1 C9 . -72.50(9) ?
C5 C4 N2 C8 . -0.90(14) ?
C3 C4 N2 C8 . 176.42(8) ?
C7 C8 N2 C4 . 0.48(16) ?
C11 C10 N3 C14 . 0.60(13) ?
C9 C10 N3 C14 . -178.97(7) ?
C13 C14 N3 C10 . -0.04(13) ?
