#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/51/2235192.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_2235192
loop_
_publ_author_name
'Shin, Jong Won'
'Min, Kil Sik'
_publ_section_title
;
 N,N,N',N'-Tetrakis(pyridin-4-yl)methanediamine
 monohydrate
;
_journal_coeditor_code           PK2409
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1600
_journal_paper_doi               10.1107/S1600536812019010
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C21 H18 N6, H2 O'
_chemical_formula_moiety         'C21 H18 N6, H2 O'
_chemical_formula_sum            'C21 H20 N6 O'
_chemical_formula_weight         372.42
_chemical_name_systematic
;
N,N,N',N'-Tetrakis(pyridin-4-yl)methanediamine
monohydrate
;
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 109.142(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.9048(11)
_cell_length_b                   13.7637(11)
_cell_length_c                   10.0569(8)
_cell_measurement_reflns_used    2155
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.18
_cell_measurement_theta_min      2.65
_cell_volume                     1818.3(3)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        'SAINT (Siemens, 1996)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Siemens SMART CCD'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0330
_diffrn_reflns_av_sigmaI/netI    0.0391
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6540
_diffrn_reflns_theta_full        28.27
_diffrn_reflns_theta_max         28.27
_diffrn_reflns_theta_min         2.14
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_correction_T_min  0.973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.218
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     130
_refine_ls_number_reflns         2241
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0998
_refine_ls_R_factor_gt           0.0505
_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)+(0.0744P)²+0.1675P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1257
_refine_ls_wR_factor_ref         0.1625
_reflns_number_gt                1313
_reflns_number_total             2241
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            pk2409.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2235192
_cod_database_fobs_code          2235192
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
_atom_site_symmetry_multiplicity
N N1 0.08225(11) 0.18977(10) 0.72834(16) 0.0378(4) Uani d . 1 1
N N2 0.32207(12) 0.08225(11) 1.07690(17) 0.0456(4) Uani d . 1 1
N N3 0.12205(15) 0.19990(14) 0.3297(2) 0.0627(6) Uani d . 1 1
C C1 0.24926(14) 0.11276(13) 0.8290(2) 0.0415(5) Uani d . 1 1
H H1 0.2569 0.1085 0.7387 0.050 Uiso calc R 1 1
C C2 0.32458(14) 0.07990(13) 0.9453(2) 0.0455(5) Uani d . 1 1
H H2 0.3836 0.0532 0.9315 0.055 Uiso calc R 1 1
C C3 0.23734(15) 0.12101(13) 1.0907(2) 0.0444(5) Uani d . 1 1
H H3 0.2327 0.1249 1.1827 0.053 Uiso calc R 1 1
C C4 0.15609(14) 0.15572(12) 0.9798(2) 0.0388(5) Uani d . 1 1
H H4 0.0977 0.1813 0.9966 0.047 Uiso calc R 1 1
C C5 0.16063(13) 0.15281(11) 0.84383(19) 0.0356(4) Uani d . 1 1
C C6 0.09476(13) 0.19319(12) 0.5933(2) 0.0373(4) Uani d . 1 1
C C7 0.09792(15) 0.28090(13) 0.5269(2) 0.0461(5) Uani d . 1 1
H H7 0.0918 0.3406 0.5708 0.055 Uiso calc R 1 1
C C8 0.11000(16) 0.28004(16) 0.3965(2) 0.0569(6) Uani d . 1 1
H H8 0.1097 0.3407 0.3512 0.068 Uiso calc R 1 1
C C9 0.11687(16) 0.11622(16) 0.3940(2) 0.0555(6) Uani d . 1 1
H H9 0.1238 0.0577 0.3480 0.067 Uiso calc R 1 1
C C10 0.10220(14) 0.10896(14) 0.5221(2) 0.0452(5) Uani d . 1 1
H H10 0.0972 0.0471 0.5613 0.054 Uiso calc R 1 1
C C11 0.0000 0.24732(13) 0.7500 0.0355(6) Uani d S 1 2
H H11A 0.0293 0.2898 0.8329 0.043 Uiso calc PR 0.50 1
H H11B -0.0293 0.2898 0.6671 0.043 Uiso calc PR 0.50 1
O O1 0.4878(6) 0.01031(13) 0.7761(8) 0.0617(12) Uani d PR 0.50 1
H H1W 0.5532 -0.0300 0.8088 0.130(11) Uiso d R 1 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_site_symmetry_1
_geom_angle
C5 N1 C6 . 119.78(14)
C5 N1 C11 . 120.38(13)
C6 N1 C11 . 117.96(12)
C2 N2 C3 . 114.92(16)
C8 N3 C9 . 115.77(19)
C2 C1 C5 . 119.54(18)
C2 C1 H1 . 120.2
C5 C1 H1 . 120.2
N2 C2 C1 . 125.35(19)
N2 C2 H2 . 117.3
C1 C2 H2 . 117.3
N2 C3 C4 . 124.43(18)
N2 C3 H3 . 117.8
C4 C3 H3 . 117.8
C3 C4 C5 . 119.59(17)
C3 C4 H4 . 120.2
C5 C4 H4 . 120.2
C4 C5 C1 . 116.16(16)
C4 C5 N1 . 122.06(16)
C1 C5 N1 . 121.76(17)
C10 C6 C7 . 117.39(18)
C10 C6 N1 . 121.22(15)
C7 C6 N1 . 121.38(16)
C8 C7 C6 . 118.99(18)
C8 C7 H7 . 120.5
C6 C7 H7 . 120.5
N3 C8 C7 . 124.30(18)
N3 C8 H8 . 117.8
C7 C8 H8 . 117.8
N3 C9 C10 . 124.49(19)
N3 C9 H9 . 117.8
C10 C9 H9 . 117.8
C9 C10 C6 . 118.94(17)
C9 C10 H10 . 120.5
C6 C10 H10 . 120.5
N1 C11 N1 2_556 114.54(16)
N1 C11 H11A 2_556 108.6
N1 C11 H11A . 108.6
N1 C11 H11B 2_556 108.6
N1 C11 H11B . 108.6
H11A C11 H11B . 107.6
O1 O1 H1W 2_656 69.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
N1 C5 . 1.402(2)
N1 C6 . 1.425(2)
N1 C11 . 1.4649(17)
N2 C2 . 1.335(2)
N2 C3 . 1.341(2)
N3 C8 . 1.330(3)
N3 C9 . 1.335(3)
C1 C2 . 1.366(3)
C1 C5 . 1.402(2)
C1 H1 . 0.9500
C2 H2 . 0.9500
C3 C4 . 1.387(3)
C3 H3 . 0.9500
C4 C5 . 1.390(2)
C4 H4 . 0.9500
C6 C10 . 1.384(3)
C6 C7 . 1.387(2)
C7 C8 . 1.376(3)
C7 H7 . 0.9500
C8 H8 . 0.9500
C9 C10 . 1.373(3)
C9 H9 . 0.9500
C10 H10 . 0.9500
C11 N1 2_556 1.4649(17)
C11 H11A . 0.9900
C11 H11B . 0.9900
O1 O1 2_656 0.7127
O1 H1W . 1.0230
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
O1 H1W N2 5_657 1.023 1.881 2.869(2) 161.38 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_site_symmetry_4
_geom_torsion
C3 N2 C2 C1 . -0.3(3)
C5 C1 C2 N2 . 0.0(3)
C2 N2 C3 C4 . 0.8(3)
N2 C3 C4 C5 . -1.1(3)
C3 C4 C5 C1 . 0.7(2)
C3 C4 C5 N1 . -177.87(15)
C2 C1 C5 C4 . -0.2(2)
C2 C1 C5 N1 . 178.37(16)
C6 N1 C5 C4 . 174.20(15)
C11 N1 C5 C4 . 10.1(2)
C6 N1 C5 C1 . -4.3(2)
C11 N1 C5 C1 . -168.41(15)
C5 N1 C6 C10 . 65.9(2)
C11 N1 C6 C10 . -129.57(17)
C5 N1 C6 C7 . -115.35(19)
C11 N1 C6 C7 . 49.1(2)
C10 C6 C7 C8 . -1.2(3)
N1 C6 C7 C8 . -179.92(17)
C9 N3 C8 C7 . 3.2(3)
C6 C7 C8 N3 . -2.1(3)
C8 N3 C9 C10 . -1.2(3)
N3 C9 C10 C6 . -1.8(3)
C7 C6 C10 C9 . 2.9(3)
N1 C6 C10 C9 . -178.31(17)
C5 N1 C11 N1 2_556 -82.93(13)
C6 N1 C11 N1 2_556 112.69(14)
