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#$Date: 2023-10-16 10:32:26 +0300 (Mon, 16 Oct 2023) $
#$Revision: 286982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/76/8107629.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_8107629
loop_
_publ_author_name
'Wang, Zhi-Yong'
'Qian, Peng-Xin'
'Yang, Xian-Jiong'
'Zhang, Qi-Long'
'Xu, Hong'
'Huang, Ya-Li'
_publ_section_title
;
 Crystal structure of 6-(pyridin-3-yl)-1,3,5-triazine-2,4-diamine-sebacic
 acid (2/1), C13H17N6O2
;
_journal_issue                   5
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              1025
_journal_page_last               1026
_journal_paper_doi               10.1515/ncrs-2023-0336
_journal_volume                  238
_journal_year                    2023
_chemical_formula_moiety         'C8 H8 N6, C5 H9 O2'
_chemical_formula_sum            'C13 H17 N6 O2'
_chemical_formula_weight         289.32
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 92.707(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.2666(17)
_cell_length_b                   11.0435(15)
_cell_length_c                   19.778(3)
_cell_measurement_reflns_used    1005
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.17
_cell_measurement_theta_min      2.71
_cell_volume                     2894.4(7)
_computing_cell_refinement       'SAINT (Brucker, 2012)[2]'
_computing_data_collection       'APEX2 (Brucker, 2012)[2]'
_computing_data_reduction        'SAINT (Brucker, 2012)[2]'
_computing_molecular_graphics    'Diamond 4.0[4]'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)[1]'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)[3]'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0809
_diffrn_reflns_av_unetI/netI     0.0794
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9157
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.989
_diffrn_reflns_theta_max         24.989
_diffrn_reflns_theta_min         2.062
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.9799
_exptl_absorpt_correction_T_min  0.9782
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1224
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       0.0010(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   0.930
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2547
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.930
_refine_ls_R_factor_all          0.1266
_refine_ls_R_factor_gt           0.0528
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0578P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1137
_refine_ls_wR_factor_ref         0.1511
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1186
_reflns_number_total             2547
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2023-0336_suppl_001.cif
_cod_data_source_block           a
_cod_database_code               8107629
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.987
_shelx_estimated_absorpt_t_min   0.983
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8)
2.c X=CH2 refined with riding coordinates:
 N2(H2A,H2B), N5(H5A,H5B)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.0285(2) 0.1348(3) 0.38777(16) 0.0493(8) Uani 1 1 d . . . . .
C2 C 0.8696(2) 0.1300(3) 0.42480(17) 0.0520(8) Uani 1 1 d . . . . .
C3 C 1.0022(2) 0.1594(2) 0.49828(15) 0.0454(7) Uani 1 1 d . . . . .
C4 C 1.0437(2) 0.1748(3) 0.56877(15) 0.0464(8) Uani 1 1 d . . . . .
C5 C 0.9835(2) 0.1850(3) 0.62318(16) 0.0588(9) Uani 1 1 d . . . . .
H5 H 0.9137 0.1873 0.6164 0.071 Uiso 1 1 calc R . . . .
C6 C 1.1476(2) 0.1747(3) 0.58281(16) 0.0569(9) Uani 1 1 d . . . . .
H6 H 1.1895 0.1692 0.5466 0.068 Uiso 1 1 calc R . . . .
C7 C 1.1296(2) 0.1899(3) 0.69621(16) 0.0608(9) Uani 1 1 d . . . . .
H7 H 1.1584 0.1943 0.7399 0.073 Uiso 1 1 calc R . . . .
C8 C 1.0266(2) 0.1920(3) 0.68766(17) 0.0644(10) Uani 1 1 d . . . . .
H8 H 0.9864 0.1980 0.7248 0.077 Uiso 1 1 calc R . . . .
C9 C 0.9895(2) 0.4906(3) 0.46228(15) 0.0654(9) Uani 1 1 d . . . . .
H9A H 1.0240 0.4179 0.4484 0.079 Uiso 1 1 calc R . . . .
H9B H 1.0172 0.5584 0.4381 0.079 Uiso 1 1 calc R . . . .
C10 C 0.8779(2) 0.4791(3) 0.44233(17) 0.0688(10) Uani 1 1 d . . . . .
H10A H 0.8500 0.4116 0.4667 0.083 Uiso 1 1 calc R . . . .
H10B H 0.8434 0.5520 0.4558 0.083 Uiso 1 1 calc R . . . .
C11 C 0.8578(2) 0.4596(3) 0.36693(17) 0.0688(10) Uani 1 1 d . . . . .
H11A H 0.8856 0.5271 0.3425 0.083 Uiso 1 1 calc R . . . .
H11B H 0.8922 0.3866 0.3533 0.083 Uiso 1 1 calc R . . . .
C12 C 0.7466(2) 0.4484(4) 0.34770(17) 0.0757(11) Uani 1 1 d . . . . .
H12A H 0.7186 0.3833 0.3739 0.091 Uiso 1 1 calc R . . . .
H12B H 0.7131 0.5227 0.3599 0.091 Uiso 1 1 calc R . . . .
C13 C 0.7238(2) 0.4240(3) 0.27420(18) 0.0670(10) Uani 1 1 d . . . . .
N1 N 0.92914(16) 0.1220(2) 0.37212(12) 0.0528(7) Uani 1 1 d . . . . .
N2 N 1.09129(17) 0.1264(2) 0.33802(13) 0.0684(9) Uani 1 1 d . . . . .
H2A H 1.1552 0.1340 0.3464 0.082 Uiso 1 1 calc R . . . .
H2B H 1.0683 0.1133 0.2973 0.082 Uiso 1 1 calc R . . . .
N3 N 1.06854(16) 0.1552(2) 0.45034(12) 0.0499(7) Uani 1 1 d . . . . .
N4 N 0.90183(15) 0.1480(2) 0.48956(12) 0.0511(7) Uani 1 1 d . . . . .
N5 N 0.77033(16) 0.1188(3) 0.41081(13) 0.0691(9) Uani 1 1 d . . . . .
H5A H 0.7480 0.1072 0.3698 0.083 Uiso 1 1 calc R . . . .
H5B H 0.7288 0.1233 0.4428 0.083 Uiso 1 1 calc R . . . .
N6 N 1.19039(17) 0.1820(3) 0.64490(13) 0.0639(8) Uani 1 1 d . . . . .
O1 O 0.78647(16) 0.4182(3) 0.23236(12) 0.0930(9) Uani 1 1 d . . . . .
O2 O 0.62676(14) 0.4110(3) 0.25933(11) 0.0802(8) Uani 1 1 d . . . . .
H2 H 0.6181 0.3926 0.2193 0.120 Uiso 1 1 calc GR . . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
N2 C1 N1 117.8(3) . .
N2 C1 N3 117.5(3) . .
N3 C1 N1 124.7(3) . .
N1 C2 N4 125.3(2) . .
N5 C2 N1 116.3(3) . .
N5 C2 N4 118.4(3) . .
N3 C3 C4 116.6(2) . .
N3 C3 N4 126.5(3) . .
N4 C3 C4 116.9(3) . .
C5 C4 C3 122.8(3) . .
C5 C4 C6 116.7(3) . .
C6 C4 C3 120.4(3) . .
C4 C5 H5 120.0 . .
C4 C5 C8 120.0(3) . .
C8 C5 H5 120.0 . .
C4 C6 H6 118.0 . .
N6 C6 C4 124.0(3) . .
N6 C6 H6 118.0 . .
C8 C7 H7 118.5 . .
N6 C7 H7 118.5 . .
N6 C7 C8 123.0(3) . .
C5 C8 H8 120.6 . .
C7 C8 C5 118.8(3) . .
C7 C8 H8 120.6 . .
C9 C9 H9A 108.9 5_766 .
C9 C9 H9B 108.9 5_766 .
C9 C9 C10 113.4(4) 5_766 .
H9A C9 H9B 107.7 . .
C10 C9 H9A 108.9 . .
C10 C9 H9B 108.9 . .
C9 C10 H10A 109.0 . .
C9 C10 H10B 109.0 . .
H10A C10 H10B 107.8 . .
C11 C10 C9 113.0(3) . .
C11 C10 H10A 109.0 . .
C11 C10 H10B 109.0 . .
C10 C11 H11A 109.1 . .
C10 C11 H11B 109.1 . .
H11A C11 H11B 107.8 . .
C12 C11 C10 112.5(3) . .
C12 C11 H11A 109.1 . .
C12 C11 H11B 109.1 . .
C11 C12 H12A 108.7 . .
C11 C12 H12B 108.7 . .
H12A C12 H12B 107.6 . .
C13 C12 C11 114.2(3) . .
C13 C12 H12A 108.7 . .
C13 C12 H12B 108.7 . .
O1 C13 C12 124.4(3) . .
O1 C13 O2 122.8(3) . .
O2 C13 C12 112.8(3) . .
C2 N1 C1 114.9(3) . .
C1 N2 H2A 120.0 . .
C1 N2 H2B 120.0 . .
H2A N2 H2B 120.0 . .
C3 N3 C1 114.7(2) . .
C3 N4 C2 113.9(3) . .
C2 N5 H5A 120.0 . .
C2 N5 H5B 120.0 . .
H5A N5 H5B 120.0 . .
C7 N6 C6 117.4(3) . .
C13 O2 H2 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.347(3) .
C1 N2 1.322(3) .
C1 N3 1.343(3) .
C2 N1 1.340(3) .
C2 N4 1.346(3) .
C2 N5 1.339(3) .
C3 C4 1.484(4) .
C3 N3 1.324(3) .
C3 N4 1.341(3) .
C4 C5 1.374(4) .
C4 C6 1.393(3) .
C5 H5 0.9300 .
C5 C8 1.375(4) .
C6 H6 0.9300 .
C6 N6 1.331(3) .
C7 H7 0.9300 .
C7 C8 1.370(4) .
C7 N6 1.328(4) .
C8 H8 0.9300 .
C9 C9 1.519(6) 5_766
C9 H9A 0.9700 .
C9 H9B 0.9700 .
C9 C10 1.520(4) .
C10 H10A 0.9700 .
C10 H10B 0.9700 .
C10 C11 1.518(4) .
C11 H11A 0.9700 .
C11 H11B 0.9700 .
C11 C12 1.512(4) .
C12 H12A 0.9700 .
C12 H12B 0.9700 .
C12 C13 1.495(4) .
C13 O1 1.202(4) .
C13 O2 1.315(3) .
N2 H2A 0.8600 .
N2 H2B 0.8600 .
N5 H5A 0.8600 .
N5 H5B 0.8600 .
O2 H2 0.8200 .
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
N2 H2A N6 0.86 2.12 2.964(3) 169.1 2_756
N5 H5A O1 0.86 2.07 2.924(3) 172.6 7_655
N5 H5B N4 0.86 2.26 3.103(3) 168.6 2_656
O2 H2 N1 0.82 1.89 2.694(3) 165.5 7_655
