#------------------------------------------------------------------------------
#$Date: 2023-03-04 19:17:47 +0100 (Sat 04 de Mar de 2023) $
#$Revision: 281445 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/61/7246129.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_7246129
loop_
_publ_author_name
'Abidi, Adela'
'Fortin, Emmanuelle'
'Larocque, Kariane'
'Essalhi, Mohamed'
'Dissem, Nour'
'Chartrand, Daniel'
'Maris, Thierry'
'Duong, Adam'
_publ_section_title
;
 Missing puzzle in crystal engineering: 2-pyridone and
 [1,3,5]-triazine-2,4-diamine, the two most common cyclic hydrogen bonding
 sticky sites, in a single core
;
_journal_issue                   6
_journal_name_full               CrystEngComm
_journal_page_first              1018
_journal_page_last               1028
_journal_paper_doi               10.1039/D2CE01505F
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C11 H14 N6 O2, H2 O'
_chemical_formula_sum            'C11 H16 N6 O3'
_chemical_formula_weight         280.30
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-04-24
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-04-28 deposited with the CCDC.	2023-01-13 downloaded from the CCDC.
;
_cell_angle_alpha                72.622(3)
_cell_angle_beta                 88.326(3)
_cell_angle_gamma                68.746(3)
_cell_formula_units_Z            2
_cell_length_a                   8.0907(5)
_cell_length_b                   8.6941(5)
_cell_length_c                   10.2522(7)
_cell_measurement_reflns_used    4113
_cell_measurement_temperature    100
_cell_measurement_theta_max      71.302
_cell_measurement_theta_min      4.537
_cell_volume                     638.89(7)
_computing_cell_refinement
;
SAINT (2020) V8.40B; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_collection
;
APEX 3 (2019) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction
;
SAINT (2020) V8.40B; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean 8.3
_diffrn_detector_type            'Bruker APEX2 CCD'
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker Smart APEX'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12441
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         71.502
_diffrn_reflns_theta_min         4.537
_exptl_absorpt_coefficient_mu    0.923
_exptl_absorpt_correction_T_max  0.7535
_exptl_absorpt_correction_T_min  0.6646
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. 
wR2(int) was 0.1274 before and 0.0407 after correction. 
The Ratio of minimum to maximum transmission is 0.9274. 
The λ/2 correction factor is Not present.'
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.457
_exptl_crystal_description       needle
_exptl_crystal_F_000             296
_exptl_crystal_recrystallization_method 'crystallised in H2O'
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     206
_refine_ls_number_reflns         2444
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0437
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0742P)²+0.2171P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1178
_refine_ls_wR_factor_ref         0.1256
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2124
_reflns_number_total             2444
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ce01505f2.cif
_cod_data_source_block           cmpd2
_cod_depositor_comments
'Adding full bibliography for 7246127--7246132.cif.'
_cod_database_code               7246129
_shelx_shelxl_version_number     2018/3
_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   0.955
_shelx_estimated_absorpt_t_min   0.874
_diffrn_measurement_ambient_temperature_device_make 'Oxford Cryostream 700'
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_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_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
O1 O 0.88882(14) 0.77162(13) 0.25864(11) 0.0221(3) Uani 1 1 d . . . . .
O2 O 0.85320(15) 1.21535(14) 0.15418(12) 0.0256(3) Uani 1 1 d . . . . .
N1 N 0.73986(17) 0.69811(16) 0.44864(14) 0.0212(3) Uani 1 1 d . . . . .
N2 N 0.61035(16) 0.32008(16) 0.74344(13) 0.0188(3) Uani 1 1 d . . . . .
N3 N 0.58642(17) 0.04068(16) 0.81885(13) 0.0200(3) Uani 1 1 d . . . . .
N4 N 0.71064(17) 0.13000(16) 0.60713(13) 0.0198(3) Uani 1 1 d . . . . .
N5 N 0.49087(18) 0.22901(17) 0.94508(14) 0.0219(3) Uani 1 1 d . . . . .
H5A H 0.483(3) 0.320(3) 0.965(2) 0.034(5) Uiso 1 1 d . . . . .
H5B H 0.467(2) 0.152(3) 1.005(2) 0.020(4) Uiso 1 1 d . . . . .
N6 N 0.67718(19) -0.13293(18) 0.67979(15) 0.0257(3) Uani 1 1 d . . . . .
H6A H 0.637(3) -0.205(3) 0.735(2) 0.022(4) Uiso 1 1 d . . . . .
H6B H 0.711(3) -0.146(3) 0.601(2) 0.034(6) Uiso 1 1 d . . . . .
C1 C 0.83518(19) 0.6544(2) 0.34932(16) 0.0200(3) Uani 1 1 d . . . . .
C2 C 0.8855(2) 0.4905(2) 0.33060(15) 0.0215(3) Uani 1 1 d . . . . .
H2 H 0.952299 0.465805 0.256611 0.026 Uiso 1 1 calc R U . . .
C3 C 0.8359(2) 0.36706(19) 0.42182(16) 0.0213(3) Uani 1 1 d . . . . .
H3 H 0.868104 0.254869 0.411981 0.026 Uiso 1 1 calc R U . . .
C4 C 0.73708(19) 0.40792(19) 0.53001(15) 0.0189(3) Uani 1 1 d . . . . .
C5 C 0.6920(2) 0.5752(2) 0.53703(15) 0.0204(3) Uani 1 1 d . . . . .
H5 H 0.622969 0.604779 0.608703 0.024 Uiso 1 1 calc R U . . .
C6 C 0.68286(18) 0.27792(19) 0.63341(15) 0.0186(3) Uani 1 1 d . . . . .
C7 C 0.56425(19) 0.19575(19) 0.83332(16) 0.0191(3) Uani 1 1 d . . . . .
C8 C 0.65693(19) 0.01637(19) 0.70253(16) 0.0204(3) Uani 1 1 d . . . . .
C9 C 0.8388(2) 0.94115(19) 0.27587(16) 0.0221(3) Uani 1 1 d . . . . .
H9A H 0.897205 0.934092 0.362110 0.027 Uiso 1 1 calc R U . . .
H9B H 0.708122 0.995390 0.276705 0.027 Uiso 1 1 calc R U . . .
C10 C 0.9038(2) 1.04165(19) 0.15225(15) 0.0208(3) Uani 1 1 d . . . . .
H10A H 1.034997 0.987961 0.154719 0.025 Uiso 1 1 calc R U . . .
H10B H 0.850926 1.039964 0.067074 0.025 Uiso 1 1 calc R U . . .
C11 C 0.9131(2) 1.3157(2) 0.03977(18) 0.0293(4) Uani 1 1 d . . . . .
H11A H 0.871183 1.306304 -0.045212 0.044 Uiso 1 1 calc R U . . .
H11B H 1.043515 1.272194 0.048380 0.044 Uiso 1 1 calc R U . . .
H11C H 0.865756 1.437472 0.037517 0.044 Uiso 1 1 calc R U . . .
O3 O 0.51572(17) 0.61575(15) 0.83564(12) 0.0253(3) Uani 1 1 d . . . . .
H3A H 0.541(3) 0.535(3) 0.801(2) 0.032(5) Uiso 1 1 d . . . . .
H3B H 0.402(4) 0.667(3) 0.828(3) 0.049(7) Uiso 1 1 d . . . . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C9 117.56(12) . . ?
C10 O2 C11 110.87(12) . . ?
C1 N1 C5 116.93(13) . . ?
C6 N2 C7 114.39(12) . . ?
C7 N3 C8 114.50(13) . . ?
C6 N4 C8 114.45(13) . . ?
H5A N5 H5B 117.2(19) . . ?
C7 N5 H5A 122.2(15) . . ?
C7 N5 H5B 119.8(13) . . ?
H6A N6 H6B 120.7(18) . . ?
C8 N6 H6A 119.4(13) . . ?
C8 N6 H6B 118.7(14) . . ?
O1 C1 C2 116.54(13) . . ?
N1 C1 O1 119.56(14) . . ?
N1 C1 C2 123.90(14) . . ?
C1 C2 H2 120.9 . . ?
C3 C2 C1 118.29(14) . . ?
C3 C2 H2 120.9 . . ?
C2 C3 H3 120.3 . . ?
C2 C3 C4 119.40(14) . . ?
C4 C3 H3 120.3 . . ?
C3 C4 C6 121.63(13) . . ?
C5 C4 C3 117.32(14) . . ?
C5 C4 C6 121.05(14) . . ?
N1 C5 C4 124.14(14) . . ?
N1 C5 H5 117.9 . . ?
C4 C5 H5 117.9 . . ?
N2 C6 C4 117.55(13) . . ?
N4 C6 N2 126.16(14) . . ?
N4 C6 C4 116.28(13) . . ?
N3 C7 N2 125.10(14) . . ?
N5 C7 N2 117.66(13) . . ?
N5 C7 N3 117.23(14) . . ?
N3 C8 N4 125.35(13) . . ?
N6 C8 N3 117.50(14) . . ?
N6 C8 N4 117.15(14) . . ?
O1 C9 H9A 111.1 . . ?
O1 C9 H9B 111.1 . . ?
O1 C9 C10 103.51(12) . . ?
H9A C9 H9B 109.0 . . ?
C10 C9 H9A 111.1 . . ?
C10 C9 H9B 111.1 . . ?
O2 C10 C9 108.66(12) . . ?
O2 C10 H10A 110.0 . . ?
O2 C10 H10B 110.0 . . ?
C9 C10 H10A 110.0 . . ?
C9 C10 H10B 110.0 . . ?
H10A C10 H10B 108.3 . . ?
O2 C11 H11A 109.5 . . ?
O2 C11 H11B 109.5 . . ?
O2 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
H3A O3 H3B 109(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.3500(18) . ?
O1 C9 1.4444(17) . ?
O2 C10 1.4204(18) . ?
O2 C11 1.4260(19) . ?
N1 C1 1.323(2) . ?
N1 C5 1.347(2) . ?
N2 C6 1.343(2) . ?
N2 C7 1.354(2) . ?
N3 C7 1.3470(19) . ?
N3 C8 1.348(2) . ?
N4 C6 1.331(2) . ?
N4 C8 1.353(2) . ?
N5 H5A 0.85(2) . ?
N5 H5B 0.84(2) . ?
N5 C7 1.335(2) . ?
N6 H6A 0.86(2) . ?
N6 H6B 0.87(2) . ?
N6 C8 1.338(2) . ?
C1 C2 1.404(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.371(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.405(2) . ?
C4 C5 1.389(2) . ?
C4 C6 1.487(2) . ?
C5 H5 0.9500 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.510(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
O3 H3A 0.83(2) . ?
O3 H3B 0.86(3) . ?
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
_geom_hbond_publ_flag
N5 H5A O3 0.85(2) 2.27(2) 2.9380(18) 134.8(19) 2_667 yes
N5 H5B N3 0.84(2) 2.22(2) 3.0547(19) 173.5(18) 2_657 yes
N6 H6A O3 0.86(2) 2.13(2) 2.9826(18) 168.5(18) 1_545 yes
N6 H6B N1 0.87(2) 2.32(2) 3.0822(19) 147.3(18) 1_545 yes
O3 H3A N2 0.83(2) 2.01(2) 2.8408(17) 173(2) . yes
O3 H3B O2 0.86(3) 1.97(3) 2.8235(17) 169(2) 2_676 yes
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 179.03(13) . . . . ?
O1 C9 C10 O2 176.95(11) . . . . ?
N1 C1 C2 C3 -1.2(2) . . . . ?
C1 O1 C9 C10 -174.88(11) . . . . ?
C1 N1 C5 C4 0.3(2) . . . . ?
C1 C2 C3 C4 0.1(2) . . . . ?
C2 C3 C4 C5 1.1(2) . . . . ?
C2 C3 C4 C6 -178.78(13) . . . . ?
C3 C4 C5 N1 -1.3(2) . . . . ?
C3 C4 C6 N2 171.05(13) . . . . ?
C3 C4 C6 N4 -9.2(2) . . . . ?
C5 N1 C1 O1 -179.22(12) . . . . ?
C5 N1 C1 C2 1.0(2) . . . . ?
C5 C4 C6 N2 -8.8(2) . . . . ?
C5 C4 C6 N4 170.94(13) . . . . ?
C6 N2 C7 N3 0.1(2) . . . . ?
C6 N2 C7 N5 -179.83(13) . . . . ?
C6 N4 C8 N3 -2.4(2) . . . . ?
C6 N4 C8 N6 178.29(13) . . . . ?
C6 C4 C5 N1 178.54(13) . . . . ?
C7 N2 C6 N4 0.3(2) . . . . ?
C7 N2 C6 C4 -179.97(12) . . . . ?
C7 N3 C8 N4 2.7(2) . . . . ?
C7 N3 C8 N6 -177.93(13) . . . . ?
C8 N3 C7 N2 -1.5(2) . . . . ?
C8 N3 C7 N5 178.43(13) . . . . ?
C8 N4 C6 N2 0.7(2) . . . . ?
C8 N4 C6 C4 -179.00(12) . . . . ?
C9 O1 C1 N1 0.3(2) . . . . ?
C9 O1 C1 C2 -179.94(12) . . . . ?
C11 O2 C10 C9 179.49(12) . . . . ?
