#------------------------------------------------------------------------------
#$Date: 2020-10-02 17:43:13 +0300 (Fri, 02 Oct 2020) $
#$Revision: 256941 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/15/1501550.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_1501550
loop_
_publ_author_name
'Adam Duong'
'Marc-André Dubois'
'Thierry Maris'
'Valérie Métivaud'
'Ji-Hyun Yi'
'Antonio Nanci'
'Alain Rochefort'
'Wuest,James D'
_publ_section_title
;
 Engineering Homologous Molecular Organization in 2D and 3D.
 Cocrystallization of Pyridyl-Substituted Diaminotriazines with
 Alkanecarboxylic Acids
;
_journal_name_full               'The Journal of Physical Chemistry C'
_journal_page_first              12908
_journal_page_last               12919
_journal_paper_doi               10.1021/jp201119g
_journal_volume                  115
_journal_year                    2011
_chemical_compound_source        'Synthesized by the authors. See text'
_chemical_formula_moiety         'C8 H16 O2, C8 H8 N6'
_chemical_formula_sum            'C16 H24 N6 O2'
_chemical_formula_weight         332.41
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                104.685(2)
_cell_angle_beta                 90.861(2)
_cell_angle_gamma                98.832(3)
_cell_formula_units_Z            2
_cell_length_a                   8.8653(4)
_cell_length_b                   9.4282(4)
_cell_length_c                   10.7014(5)
_cell_measurement_reflns_used    8454
_cell_measurement_temperature    150
_cell_measurement_theta_max      69.07
_cell_measurement_theta_min      4.28
_cell_volume                     853.62(7)
_computing_cell_refinement       'SAINT V7.68A(Bruker AXS, 2009)'
_computing_data_collection       'APEX2  (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.68A(Bruker AXS, 2009)'
_computing_molecular_graphics    'SHELXTL v6.12 (Bruker AXS, 2001)'
_computing_publication_material  'UdMX (Maris, 2004)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al., 2004)'
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'Bruker Microstar'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  'Helios optics'
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.036
_diffrn_reflns_av_sigmaI/netI    0.0411
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            14242
_diffrn_reflns_theta_full        69.30
_diffrn_reflns_theta_max         69.30
_diffrn_reflns_theta_min         4.28
_exptl_absorpt_coefficient_mu    0.726
_exptl_absorpt_correction_T_max  0.9785
_exptl_absorpt_correction_T_min  0.6001
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 2008)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.555
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.099
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3105
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0744
_refine_ls_R_factor_gt           0.0701
_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)+(0.1539P)²+0.1124P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1849
_refine_ls_wR_factor_ref         0.1955
_reflns_number_gt                2749
_reflns_number_total             3105
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            deposit.cif
_cod_data_source_block           adam55
_cod_depositor_comments
;
 Updated values of the _geom_bond_atom_site_label_* data items to establish
 relationships between loop packets from different data loops.

 Antanas Vaitkus,
 2020-10-02
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1501550
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
O1 O 0.47582(15) 1.31235(14) 1.01988(13) 0.0426(4) Uani 1 1 d .
O2 O 0.42854(14) 1.13557(14) 0.83620(13) 0.0402(4) Uani 1 1 d .
H2 H 0.3508 1.1755 0.8322 0.060 Uiso 1 1 calc .
C1 C 0.51109(18) 1.20558(18) 0.94235(16) 0.0279(4) Uani 1 1 d .
C2 C 0.65414(18) 1.14146(18) 0.96042(16) 0.0291(4) Uani 1 1 d .
H2A H 0.6486 1.1093 1.0416 0.035 Uiso 1 1 calc R
H2B H 0.7436 1.2213 0.9709 0.035 Uiso 1 1 calc R
C3 C 0.68088(18) 1.01053(17) 0.85080(16) 0.0277(4) Uani 1 1 d .
H3A H 0.6833 1.0406 0.7686 0.033 Uiso 1 1 calc R
H3B H 0.5944 0.9281 0.8425 0.033 Uiso 1 1 calc R
C4 C 0.83007(18) 0.95527(18) 0.87244(16) 0.0296(4) Uani 1 1 d .
H4A H 0.9155 1.0399 0.8894 0.035 Uiso 1 1 calc R
H4B H 0.8236 0.9156 0.9498 0.035 Uiso 1 1 calc R
C5 C 0.86370(19) 0.83468(18) 0.75664(17) 0.0311(4) Uani 1 1 d .
H5A H 0.8678 0.8742 0.6792 0.037 Uiso 1 1 calc R
H5B H 0.7786 0.7498 0.7408 0.037 Uiso 1 1 calc R
C6 C 1.01377(19) 0.7785(2) 0.77407(17) 0.0324(4) Uani 1 1 d .
H6A H 1.0976 0.8646 0.7981 0.039 Uiso 1 1 calc R
H6B H 1.0060 0.7303 0.8464 0.039 Uiso 1 1 calc R
C7 C 1.0542(2) 0.6686(2) 0.65373(18) 0.0354(4) Uani 1 1 d .
H7A H 1.0548 0.7139 0.5798 0.042 Uiso 1 1 calc R
H7B H 0.9745 0.5789 0.6334 0.042 Uiso 1 1 calc R
C8 C 1.2093(2) 0.6227(2) 0.6697(2) 0.0456(5) Uani 1 1 d .
H8A H 1.2889 0.7108 0.6886 0.068 Uiso 1 1 calc R
H8B H 1.2302 0.5526 0.5897 0.068 Uiso 1 1 calc R
H8C H 1.2085 0.5751 0.7413 0.068 Uiso 1 1 calc R
C9 C -0.46436(18) 1.20357(18) 0.53206(16) 0.0291(4) Uani 1 1 d .
H9 H -0.5197 1.1266 0.4647 0.035 Uiso 1 1 calc R
C10 C -0.53069(19) 1.32911(18) 0.58261(18) 0.0306(4) Uani 1 1 d .
H10 H -0.6288 1.3371 0.5509 0.037 Uiso 1 1 calc R
C11 C -0.45003(19) 1.44185(18) 0.68024(17) 0.0313(4) Uani 1 1 d .
H11 H -0.4917 1.5292 0.7171 0.038 Uiso 1 1 calc R
C12 C -0.30684(18) 1.42488(17) 0.72335(16) 0.0270(4) Uani 1 1 d .
H12 H -0.2485 1.5009 0.7897 0.032 Uiso 1 1 calc R
C13 C -0.25027(17) 1.29500(16) 0.66789(15) 0.0223(4) Uani 1 1 d .
C14 C -0.09605(17) 1.27237(16) 0.71168(15) 0.0219(4) Uani 1 1 d .
C15 C 0.10723(17) 1.33944(16) 0.85722(15) 0.0235(4) Uani 1 1 d .
C16 C 0.10658(17) 1.15036(16) 0.67531(15) 0.0229(4) Uani 1 1 d .
N1 N -0.32752(15) 1.18515(14) 0.57283(13) 0.0257(4) Uani 1 1 d .
N2 N -0.03467(15) 1.36146(14) 0.82448(13) 0.0235(3) Uani 1 1 d .
N3 N 0.18020(14) 1.23497(14) 0.78552(13) 0.0256(4) Uani 1 1 d .
N4 N -0.03362(14) 1.16591(13) 0.63290(13) 0.0234(3) Uani 1 1 d .
N5 N 0.18004(15) 1.42551(15) 0.96535(13) 0.0303(4) Uani 1 1 d .
H5C H 0.2721 1.4128 0.9874 0.036 Uiso 1 1 calc .
H5D H 0.1363 1.4953 1.0152 0.036 Uiso 1 1 calc .
N6 N 0.17546(15) 1.04545(15) 0.60301(13) 0.0283(4) Uani 1 1 d .
H6C H 0.2665 1.0333 0.6281 0.034 Uiso 1 1 calc .
H6D H 0.1300 0.9880 0.5300 0.034 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'
O O 0.0492 0.0322 '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
C1 O2 H2 109.5 ?
O1 C1 O2 122.91(14) y
O1 C1 C2 123.08(15) y
O2 C1 C2 114.01(13) y
C1 C2 C3 115.24(14) y
C1 C2 H2A 108.5 ?
C3 C2 H2A 108.5 ?
C1 C2 H2B 108.5 ?
C3 C2 H2B 108.5 ?
H2A C2 H2B 107.5 ?
C2 C3 C4 112.59(14) y
C2 C3 H3A 109.1 ?
C4 C3 H3A 109.1 ?
C2 C3 H3B 109.1 ?
C4 C3 H3B 109.1 ?
H3A C3 H3B 107.8 ?
C5 C4 C3 112.24(14) y
C5 C4 H4A 109.2 ?
C3 C4 H4A 109.2 ?
C5 C4 H4B 109.2 ?
C3 C4 H4B 109.2 ?
H4A C4 H4B 107.9 ?
C4 C5 C6 113.66(14) y
C4 C5 H5A 108.8 ?
C6 C5 H5A 108.8 ?
C4 C5 H5B 108.8 ?
C6 C5 H5B 108.8 ?
H5A C5 H5B 107.7 ?
C7 C6 C5 113.48(15) y
C7 C6 H6A 108.9 ?
C5 C6 H6A 108.9 ?
C7 C6 H6B 108.9 ?
C5 C6 H6B 108.9 ?
H6A C6 H6B 107.7 ?
C6 C7 C8 112.67(16) y
C6 C7 H7A 109.1 ?
C8 C7 H7A 109.1 ?
C6 C7 H7B 109.1 ?
C8 C7 H7B 109.1 ?
H7A C7 H7B 107.8 ?
C7 C8 H8A 109.5 ?
C7 C8 H8B 109.5 ?
H8A C8 H8B 109.5 ?
C7 C8 H8C 109.5 ?
H8A C8 H8C 109.5 ?
H8B C8 H8C 109.5 ?
N1 C9 C10 123.77(15) y
N1 C9 H9 118.1 ?
C10 C9 H9 118.1 ?
C11 C10 C9 118.30(15) y
C11 C10 H10 120.8 ?
C9 C10 H10 120.8 ?
C10 C11 C12 118.69(14) y
C10 C11 H11 120.7 ?
C12 C11 H11 120.7 ?
C11 C12 C13 119.00(14) y
C11 C12 H12 120.5 ?
C13 C12 H12 120.5 ?
N1 C13 C12 122.73(14) y
N1 C13 C14 116.61(13) y
C12 C13 C14 120.65(14) y
N4 C14 N2 126.64(14) y
N4 C14 C13 116.42(13) y
N2 C14 C13 116.93(13) y
N5 C15 N3 117.06(13) y
N5 C15 N2 119.08(13) y
N3 C15 N2 123.86(14) y
N6 C16 N3 117.82(13) y
N6 C16 N4 118.16(13) y
N3 C16 N4 124.02(13) y
C9 N1 C13 117.51(13) y
C14 N2 C15 114.41(13) y
C16 N3 C15 116.52(13) y
C14 N4 C16 114.54(13) y
C15 N5 H5C 120.0 ?
C15 N5 H5D 120.0 ?
H5C N5 H5D 120.0 ?
C16 N6 H6C 120.0 ?
C16 N6 H6D 120.0 ?
H6C N6 H6D 120.0 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 1.217(2) y
O2 C1 1.307(2) y
O2 H2 0.8400 ?
C1 C2 1.516(2) y
C2 C3 1.523(2) y
C2 H2A 0.9900 ?
C2 H2B 0.9900 ?
C3 C4 1.529(2) y
C3 H3A 0.9900 ?
C3 H3B 0.9900 ?
C4 C5 1.522(2) y
C4 H4A 0.9900 ?
C4 H4B 0.9900 ?
C5 C6 1.531(2) y
C5 H5A 0.9900 ?
C5 H5B 0.9900 ?
C6 C7 1.521(2) y
C6 H6A 0.9900 ?
C6 H6B 0.9900 ?
C7 C8 1.523(2) y
C7 H7A 0.9900 ?
C7 H7B 0.9900 ?
C8 H8A 0.9800 ?
C8 H8B 0.9800 ?
C8 H8C 0.9800 ?
C9 N1 1.334(2) y
C9 C10 1.392(2) y
C9 H9 0.9500 ?
C10 C11 1.383(2) y
C10 H10 0.9500 ?
C11 C12 1.390(2) y
C11 H11 0.9500 ?
C12 C13 1.390(2) y
C12 H12 0.9500 ?
C13 N1 1.343(2) y
C13 C14 1.502(2) y
C14 N4 1.3342(19) y
C14 N2 1.336(2) y
C15 N5 1.325(2) y
C15 N3 1.3434(19) y
C15 N2 1.361(2) y
C16 N6 1.3272(19) y
C16 N3 1.339(2) y
C16 N4 1.3583(19) y
N5 H5C 0.8800 ?
N5 H5D 0.8800 ?
N6 H6C 0.8800 ?
N6 H6D 0.8800 ?
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
O2 H2 N3 0.84 1.8 2.6220(17) 166.7 .
N5 H5C O1 0.88 2.23 3.0795(18) 163.4 .
N5 H5D N2 0.88 2.2 3.0569(19) 165.6 2_587
N6 H6C O2 0.88 2.52 3.1866(18) 133.2 .
N6 H6D N4 0.88 2.04 2.9172(19) 173.1 2_576
