#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/62/2016264.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_2016264
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          'C27 H30 N6'
_chemical_formula_moiety         'C27 H30 N6'
_chemical_formula_sum            'C27 H30 N6'
_chemical_formula_weight         438.57
_chemical_name_systematic
;
N,N,N',N'-tetrakis(2-pyridylmethyl)propane-1,3-diamine
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 106.702(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   24.615(3)
_cell_length_b                   6.0114(11)
_cell_length_c                   17.1066(19)
_cell_measurement_reflns_used    4212
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      31.9232
_cell_measurement_theta_min      3.7811
_cell_volume                     2424.5(6)
_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 0.996
_diffrn_measured_fraction_theta_max 0.933
_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  0.0195
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            11733
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         31.76
_diffrn_reflns_theta_min         3.79
_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  0.9733
_exptl_absorpt_correction_T_min  0.9445
_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    1.202
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rhomb
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.166
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.987
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3834
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.987
_refine_ls_R_factor_gt           0.041
_refine_ls_shift/su_max          0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0612P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1114
_reflns_number_gt                2270
_reflns_number_total             3834
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hj3054.cif
_cod_data_source_block           I
_cod_original_cell_volume        2424.4(6)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2016264
_cod_database_fobs_code          2016264
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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_refinement_flags
_atom_site_occupancy
C C1 0 0.1036(3) 0.25 0.0551(4) Uani d S 1
C C2 0.03464(4) -0.03968(18) 0.20777(6) 0.0390(2) Uani d . 1
C C3 0.03637(4) 0.22770(19) 0.10117(6) 0.0416(2) Uani d . 1
C C4 0.06879(4) 0.31329(16) 0.04474(5) 0.0356(2) Uani d . 1
C C5 0.08145(4) 0.53778(18) 0.04144(7) 0.0449(3) Uani d . 1
C C6 0.11086(5) 0.6086(2) -0.01185(8) 0.0549(3) Uani d . 1
C C7 0.12658(5) 0.4560(2) -0.06086(7) 0.0531(3) Uani d . 1
C C8 0.11214(5) 0.2371(2) -0.05432(7) 0.0514(3) Uani d . 1
C C9 0.11736(4) 0.20198(18) 0.22258(6) 0.0386(2) Uani d . 1
C C10 0.16314(4) 0.05196(16) 0.27434(6) 0.0358(2) Uani d . 1
C C11 0.17418(4) -0.15789(18) 0.24891(7) 0.0464(3) Uani d . 1
C C12 0.21837(5) -0.2823(2) 0.29844(9) 0.0581(3) Uani d . 1
C C13 0.25048(5) -0.1912(2) 0.37108(9) 0.0655(4) Uani d . 1
C C14 0.23698(5) 0.0180(3) 0.39186(8) 0.0661(4) Uani d . 1
N N1 0.07053(3) 0.08069(13) 0.16600(5) 0.0362(2) Uani d . 1
N N2 0.08379(4) 0.16204(14) -0.00322(5) 0.0454(2) Uani d . 1
N N3 0.19398(4) 0.14097(16) 0.34567(5) 0.0510(2) Uani d . 1
H H1A 0.0270(6) 0.203(3) 0.2936(9) 0.094(5) Uiso d . 1
H H2A 0.0600(5) -0.1444(18) 0.2496(7) 0.050(3) Uiso d . 1
H H2B 0.0089(5) -0.1360(18) 0.1658(7) 0.045(3) Uiso d . 1
H H3A 0.0032(5) 0.1409(18) 0.0691(7) 0.051(3) Uiso d . 1
H H3B 0.0214(5) 0.3650(18) 0.1256(7) 0.052(3) Uiso d . 1
H H5 0.0700(5) 0.642(2) 0.0763(8) 0.058(3) Uiso d . 1
H H6 0.1192(6) 0.766(3) -0.0141(8) 0.071(4) Uiso d . 1
H H7 0.1467(5) 0.498(2) -0.0980(8) 0.068(4) Uiso d . 1
H H8 0.1210(5) 0.121(2) -0.0893(8) 0.068(4) Uiso d . 1
H H9A 0.1357(4) 0.2966(18) 0.1899(7) 0.047(3) Uiso d . 1
H H9B 0.1041(4) 0.3047(18) 0.2614(7) 0.045(3) Uiso d . 1
H H11 0.1508(5) -0.2103(19) 0.1972(8) 0.053(3) Uiso d . 1
H H12 0.2244(6) -0.428(2) 0.2791(8) 0.075(4) Uiso d . 1
H H13 0.2821(6) -0.274(3) 0.4083(9) 0.091(5) Uiso d . 1
H H14 0.2595(7) 0.089(2) 0.4459(10) 0.086(4) 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
_geom_angle_publ_flag
C2 C1 C2 2 111.53(14) ?
C2 C1 H1A 2 108.3(8) ?
C2 C1 H1A . 109.6(8) ?
N1 C2 C1 . 116.40(10) ?
N1 C2 H2A . 108.2(6) ?
C1 C2 H2A . 109.1(6) ?
N1 C2 H2B . 106.4(6) ?
C1 C2 H2B . 110.0(6) ?
H2A C2 H2B . 106.3(9) ?
N1 C3 C4 . 113.12(7) ?
N1 C3 H3A . 107.5(6) ?
C4 C3 H3A . 109.2(7) ?
N1 C3 H3B . 111.4(6) ?
C4 C3 H3B . 107.5(6) ?
H3A C3 H3B . 107.9(9) ?
N2 C4 C5 . 121.82(9) ?
N2 C4 C3 . 116.62(9) ?
C5 C4 C3 . 121.55(9) ?
C6 C5 C4 . 119.44(10) ?
C6 C5 H5 . 120.6(7) ?
C4 C5 H5 . 119.9(7) ?
C7 C6 C5 . 119.30(11) ?
C7 C6 H6 . 121.8(8) ?
C5 C6 H6 . 118.9(8) ?
C6 C7 C8 . 117.73(11) ?
C6 C7 H7 . 121.8(8) ?
C8 C7 H7 . 120.5(8) ?
N2 C8 C7 . 124.67(11) ?
N2 C8 H8 . 113.9(8) ?
C7 C8 H8 . 121.4(8) ?
N1 C9 C10 . 113.64(8) ?
N1 C9 H9A . 108.2(6) ?
C10 C9 H9A . 106.8(6) ?
N1 C9 H9B . 112.9(6) ?
C10 C9 H9B . 107.6(6) ?
H9A C9 H9B . 107.5(9) ?
N3 C10 C11 . 122.32(9) ?
N3 C10 C9 . 115.06(8) ?
C11 C10 C9 . 122.57(9) ?
C10 C11 C12 . 119.22(11) ?
C10 C11 H11 . 117.9(7) ?
C12 C11 H11 . 122.9(7) ?
C13 C12 C11 . 118.72(12) ?
C13 C12 H12 . 124.4(8) ?
C11 C12 H12 . 116.8(8) ?
C14 C13 C12 . 118.56(11) ?
C14 C13 H13 . 119.9(10) ?
C12 C13 H13 . 121.6(10) ?
N3 C14 C13 . 124.00(12) ?
N3 C14 H14 . 115.5(8) ?
C13 C14 H14 . 120.5(8) ?
C9 N1 C2 . 112.96(8) y
C9 N1 C3 . 111.56(8) y
C2 N1 C3 . 111.47(7) y
C8 N2 C4 . 117.03(9) y
C14 N3 C10 . 117.17(10) 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 2 1.5314(14) ?
C1 C2 . 1.5314(14) ?
C1 H1A . 1.034(15) ?
C2 N1 . 1.4757(12) y
C2 H2A . 1.020(12) ?
C2 H2B . 0.995(11) ?
C3 N1 . 1.4772(13) y
C3 C4 . 1.5086(13) ?
C3 H3A . 0.992(12) ?
C3 H3B . 1.039(12) ?
C4 N2 . 1.3455(12) y
C4 C5 . 1.3899(15) ?
C5 C6 . 1.3840(16) ?
C5 H5 . 0.960(13) ?
C6 C7 . 1.3718(18) ?
C6 H6 . 0.972(15) ?
C7 C8 . 1.3756(17) ?
C7 H7 . 0.945(13) ?
C8 N2 . 1.3436(13) y
C8 H8 . 0.984(14) ?
C9 N1 . 1.4682(12) y
C9 C10 . 1.5144(13) ?
C9 H9A . 0.992(11) ?
C9 H9B . 1.027(11) ?
C10 N3 . 1.3488(13) y
C10 C11 . 1.3865(15) ?
C11 C12 . 1.3896(16) ?
C11 H11 . 0.959(13) ?
C12 C13 . 1.3801(19) ?
C12 H12 . 0.960(14) ?
C13 C14 . 1.373(2) ?
C13 H13 . 0.986(16) ?
C14 N3 . 1.3454(15) y
C14 H14 . 1.025(16) ?
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_565 0.97(2) 2.56(2) 3.404(2) 145.0(10)
C8 H8 Cg2 6_555 0.980(10) 2.940(10) 3.700(2) 135.0(10)
C12 H12 Cg2 4_545 0.960(10) 2.880(10) 3.586(2) 131.0(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
C2 C1 C2 N1 2 -179.05(10) ?
N1 C3 C4 N2 . 67.15(11) y
N1 C3 C4 C5 . -114.10(11) y
N2 C4 C5 C6 . -0.74(15) ?
C3 C4 C5 C6 . -179.42(9) ?
C4 C5 C6 C7 . 0.48(16) ?
C5 C6 C7 C8 . -0.07(17) ?
C6 C7 C8 N2 . -0.11(18) ?
N1 C9 C10 N3 . -155.42(8) y
N1 C9 C10 C11 . 27.15(13) y
N3 C10 C11 C12 . 0.24(16) ?
C9 C10 C11 C12 . 177.48(10) ?
C10 C11 C12 C13 . -0.94(17) ?
C11 C12 C13 C14 . 0.74(19) ?
C12 C13 C14 N3 . 0.2(2) ?
C10 C9 N1 C2 . 70.39(10) ?
C10 C9 N1 C3 . -163.12(8) ?
C1 C2 N1 C9 . 66.74(10) ?
C1 C2 N1 C3 . -59.81(10) ?
C4 C3 N1 C9 . 65.75(11) ?
C4 C3 N1 C2 . -166.94(8) ?
C7 C8 N2 C4 . -0.12(17) ?
C5 C4 N2 C8 . 0.55(14) ?
C3 C4 N2 C8 . 179.30(9) ?
C13 C14 N3 C10 . -0.86(19) ?
C11 C10 N3 C14 . 0.64(15) ?
C9 C10 N3 C14 . -176.79(10) ?
