#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/00/4500013.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4500013
loop_
_publ_author_name
'Duong, Adam'
'Maris, Thierry'
'Wuest,James D'
_publ_section_title
;
 Structural Similarity of Hydrogen-Bonded Networks in Crystals of Isomeric
 Pyridyl-Substituted Diaminotriazines
;
_journal_name_full               'Cryst. Growth & Design'
_journal_page_first              287
_journal_page_last               294
_journal_paper_doi               10.1021/cg101290r
_journal_volume                  11
_journal_year                    2011
_chemical_compound_source        'Synthesized by the authors. See text'
_chemical_formula_moiety         'C8 H8 N6'
_chemical_formula_sum            'C8 H8 N6'
_chemical_formula_weight         188.20
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 120.433(1)
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   27.3388(10)
_cell_length_b                   7.1786(3)
_cell_length_c                   19.9614(7)
_cell_measurement_reflns_used    10857
_cell_measurement_temperature    200
_cell_measurement_theta_max      68.66
_cell_measurement_theta_min      2.57
_cell_volume                     3377.8(2)
_computing_cell_refinement       'SAINT V7.06A(Bruker AXS, )'
_computing_data_collection       'APEX2  (Bruker AXS, 1)'
_computing_data_reduction        'SAINT V7.06A(Bruker AXS, )'
_computing_molecular_graphics    'SHELXTL v6.12 (Bruker AXS, 2001)'
_computing_publication_material  'UdMX (Maris, 2004)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      200
_diffrn_detector_area_resol_mean 5.5
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'Bruker Smart 6000'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  'Montel 200 optics'
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.043
_diffrn_reflns_av_sigmaI/netI    0.0365
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            15868
_diffrn_reflns_theta_full        68.96
_diffrn_reflns_theta_max         68.96
_diffrn_reflns_theta_min         3.75
_exptl_absorpt_coefficient_mu    0.835
_exptl_absorpt_correction_T_max  0.9432
_exptl_absorpt_correction_T_min  0.7546
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 2004)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1568
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3056
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.153
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0408
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0650P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0986
_refine_ls_wR_factor_ref         0.0990
_reflns_number_gt                2738
_reflns_number_total             3056
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            deposit.cif
_cod_data_source_block           jiw982
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

'_geom_bond_publ_flag'
value 'Y' changed to 'y' according to the built-in table from CIF
Core dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29
(30 times).

'_geom_angle_publ_flag' value 'Y' changed to 'y'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (40 times).

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               4500013
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_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
N1 N 0.19609(11) -0.4404(4) 0.39811(14) 0.0441(7) Uani 1 1 d .
C1 C 0.24826(13) -0.3747(5) 0.42571(17) 0.0403(7) Uani 1 1 d .
H1 H 0.2793 -0.4511 0.4602 0.048 Uiso 1 1 calc R
C2 C 0.25978(12) -0.2012(5) 0.40697(16) 0.0382(7) Uani 1 1 d .
H2 H 0.2979 -0.1608 0.4282 0.046 Uiso 1 1 calc R
C3 C 0.21520(11) -0.0866(4) 0.35691(15) 0.0334(7) Uani 1 1 d .
C4 C 0.16073(13) -0.1557(5) 0.3286(2) 0.0460(8) Uani 1 1 d .
H4 H 0.1286 -0.0822 0.2950 0.055 Uiso 1 1 calc R
C5 C 0.15392(13) -0.3324(5) 0.34978(19) 0.0447(8) Uani 1 1 d .
H5 H 0.1164 -0.3792 0.3281 0.054 Uiso 1 1 calc R
C6 C 0.22476(11) 0.0971(4) 0.33020(15) 0.0328(6) Uani 1 1 d .
N2 N 0.27750(9) 0.1667(3) 0.36738(13) 0.0327(6) Uani 1 1 d .
C7 C 0.28470(10) 0.3200(4) 0.33360(14) 0.0284(6) Uani 1 1 d .
N3 N 0.24367(9) 0.4053(3) 0.27071(12) 0.0306(5) Uani 1 1 d .
C8 C 0.19248(10) 0.3280(4) 0.24060(14) 0.0281(6) Uani 1 1 d .
N4 N 0.18004(9) 0.1740(3) 0.26867(13) 0.0329(6) Uani 1 1 d .
N5 N 0.33714(9) 0.3884(3) 0.36434(13) 0.0340(6) Uani 1 1 d .
H5A H 0.3435 0.4859 0.3431 0.041 Uiso 1 1 calc .
H5B H 0.3653 0.3360 0.4058 0.041 Uiso 1 1 calc .
N6 N 0.15014(9) 0.4026(4) 0.17584(13) 0.0344(6) Uani 1 1 d .
H6A H 0.1565 0.4997 0.1544 0.041 Uiso 1 1 calc .
H6B H 0.1158 0.3547 0.1545 0.041 Uiso 1 1 calc .
N7 N 0.54157(10) 0.3156(4) 0.35640(14) 0.0381(6) Uani 1 1 d .
C9 C 0.57721(12) 0.3415(5) 0.43220(17) 0.0379(7) Uani 1 1 d .
H9 H 0.6150 0.3783 0.4485 0.046 Uiso 1 1 calc R
C10 C 0.56254(11) 0.3179(4) 0.48855(15) 0.0323(6) Uani 1 1 d .
H10 H 0.5896 0.3398 0.5417 0.039 Uiso 1 1 calc R
C11 C 0.50781(10) 0.2617(3) 0.46664(14) 0.0252(6) Uani 1 1 d .
C12 C 0.47027(11) 0.2333(4) 0.38800(15) 0.0314(6) Uani 1 1 d .
H12 H 0.4323 0.1956 0.3700 0.038 Uiso 1 1 calc R
C13 C 0.48926(12) 0.2611(5) 0.33612(16) 0.0371(7) Uani 1 1 d .
H13 H 0.4632 0.2397 0.2826 0.045 Uiso 1 1 calc R
C14 C 0.49101(10) 0.2365(3) 0.52665(14) 0.0243(5) Uani 1 1 d .
N8 N 0.53261(9) 0.2486(3) 0.60026(12) 0.0273(5) Uani 1 1 d .
C15 C 0.51579(11) 0.2276(4) 0.65339(15) 0.0287(6) Uani 1 1 d .
N9 N 0.43638(9) 0.2052(3) 0.50171(12) 0.0265(5) Uani 1 1 d .
C16 C 0.42423(11) 0.1840(4) 0.55972(15) 0.0276(6) Uani 1 1 d .
N10 N 0.46226(9) 0.1929(3) 0.63584(12) 0.0298(5) Uani 1 1 d .
N11 N 0.55613(9) 0.2397(4) 0.72784(13) 0.0384(6) Uani 1 1 d .
H11A H 0.5475 0.2252 0.7644 0.046 Uiso 1 1 calc .
H11B H 0.5914 0.2623 0.7405 0.046 Uiso 1 1 calc .
N12 N 0.36983(9) 0.1568(4) 0.53747(13) 0.0359(6) Uani 1 1 d .
H12A H 0.3596 0.1452 0.5725 0.043 Uiso 1 1 calc .
H12B H 0.3442 0.1505 0.4877 0.043 Uiso 1 1 calc .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 '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
_geom_angle_publ_flag
C5 N1 C1 116.9(3) y
N1 C1 C2 123.5(3) y
N1 C1 H1 118.3 ?
C2 C1 H1 118.3 ?
C1 C2 C3 119.5(3) y
C1 C2 H2 120.3 ?
C3 C2 H2 120.3 ?
C2 C3 C4 116.8(3) y
C2 C3 C6 122.1(3) y
C4 C3 C6 121.0(3) y
C5 C4 C3 119.1(3) y
C5 C4 H4 120.4 ?
C3 C4 H4 120.4 ?
N1 C5 C4 124.2(3) y
N1 C5 H5 117.9 ?
C4 C5 H5 117.9 ?
N4 C6 N2 125.6(3) y
N4 C6 C3 116.7(2) y
N2 C6 C3 117.7(2) y
C6 N2 C7 114.4(2) y
N5 C7 N3 117.3(2) y
N5 C7 N2 117.5(2) y
N3 C7 N2 125.1(2) y
C8 N3 C7 115.0(2) y
N3 C8 N6 117.8(2) y
N3 C8 N4 125.3(2) y
N6 C8 N4 116.8(2) y
C6 N4 C8 114.3(2) y
C7 N5 H5A 120 ?
C7 N5 H5B 120 ?
H5A N5 H5B 120 ?
C8 N6 H6A 120 ?
C8 N6 H6B 120 ?
H6A N6 H6B 120 ?
C13 N7 C9 116.1(2) y
N7 C9 C10 124.0(3) y
N7 C9 H9 118 ?
C10 C9 H9 118 ?
C9 C10 C11 119.3(2) y
C9 C10 H10 120.3 ?
C11 C10 H10 120.3 ?
C12 C11 C10 117.4(2) y
C12 C11 C14 122.5(2) y
C10 C11 C14 120.1(2) y
C13 C12 C11 118.8(2) y
C13 C12 H12 120.6 ?
C11 C12 H12 120.6 ?
N7 C13 C12 124.4(2) y
N7 C13 H13 117.8 ?
C12 C13 H13 117.8 ?
N8 C14 N9 126.4(2) y
N8 C14 C11 116.1(2) y
N9 C14 C11 117.5(2) y
C14 N8 C15 114.6(2) y
N11 C15 N10 118.7(2) y
N11 C15 N8 116.5(2) y
N10 C15 N8 124.8(2) y
C14 N9 C16 114.2(2) y
N12 C16 N10 118.6(2) y
N12 C16 N9 116.3(2) y
N10 C16 N9 125.1(2) y
C16 N10 C15 114.9(2) y
C15 N11 H11A 120 ?
C15 N11 H11B 120 ?
H11A N11 H11B 120 ?
C16 N12 H12A 120 ?
C16 N12 H12B 120 ?
H12A N12 H12B 120 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C5 1.317(4) y
N1 C1 1.328(4) y
C1 C2 1.382(5) y
C1 H1 0.95 ?
C2 C3 1.388(4) y
C2 H2 0.95 ?
C3 C4 1.389(4) y
C3 C6 1.494(4) y
C4 C5 1.379(5) y
C4 H4 0.95 ?
C5 H5 0.95 ?
C6 N4 1.337(4) y
C6 N2 1.340(3) y
N2 C7 1.357(4) y
C7 N5 1.335(3) y
C7 N3 1.335(3) y
N3 C8 1.333(3) y
C8 N6 1.335(3) y
C8 N4 1.358(4) y
N5 H5a 0.88 ?
N5 H5b 0.88 ?
N6 H6a 0.88 ?
N6 H6b 0.88 ?
N7 C13 1.333(4) y
N7 C9 1.334(4) y
C9 C10 1.383(4) y
C9 H9 0.95 ?
C10 C11 1.389(4) y
C10 H10 0.95 ?
C11 C12 1.388(4) y
C11 C14 1.495(3) y
C12 C13 1.388(4) y
C12 H12 0.95 ?
C13 H13 0.95 ?
C14 N8 1.329(3) y
C14 N9 1.333(3) y
N8 C15 1.361(3) y
C15 N11 1.331(3) y
C15 N10 1.344(3) y
N9 C16 1.365(3) y
C16 N12 1.334(3) y
C16 N10 1.339(3) y
N11 H11a 0.88 ?
N11 H11b 0.88 ?
N12 H12a 0.88 ?
N12 H12b 0.88 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N5 H5A N4 0.88 2.4 3.195(3) 150.4 4
N5 H5B N9 0.88 2.13 3.012(3) 176 .
N6 H6A N2 0.88 2.38 3.159(3) 147.3 4
N6 H6B N8 0.88 2.1 2.978(3) 177.3 8_455
N11 H11A N10 0.88 2.15 3.026(3) 172.7 2_656
N11 H11B N4 0.88 2.24 3.119(3) 177.9 8_556
N12 H12A N1 0.88 2.39 3.109(3) 138.7 7_546
N12 H12B N2 0.88 2.16 3.037(3) 173.1 .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139144272
