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
Abidi, Adela; Fortin, Emmanuelle; Larocque, Kariane; Essalhi, Mohamed; Dissem, Nour; Chartrand, Daniel; Maris, Thierry; Duong, Adam; CrystEngComm 25 (2023) 1018–1028; doi:10.1039/D2CE01505F

data_7246127
_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         'C8 H8 N6 O, C H4 O'
_chemical_formula_sum            'C9 H12 N6 O2'
_chemical_formula_weight         236.25
_chemical_name_systematic
'6-(4,6-diamino-1,3,5-triazin-2-yl)pyridin-2(1H)-one methanol solvate'
_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                94.326(5)
_cell_angle_beta                 99.044(5)
_cell_angle_gamma                110.439(5)
_cell_formula_units_Z            2
_cell_length_a                   8.1197(6)
_cell_length_b                   8.3630(6)
_cell_length_c                   8.3902(5)
_cell_measurement_reflns_used    1000
_cell_measurement_temperature    100
_cell_measurement_theta_max      69.823
_cell_measurement_theta_min      5.393
_cell_volume                     521.98(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
_diffrn_detector_area_resol_mean 8.3
_diffrn_detector_type            'Bruker APEX2 CCD'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker Smart APEX'
_diffrn_measurement_method       '\w scans'
_diffrn_measurement_specimen_support 'Hampton Research Cryoloop'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0456
_diffrn_reflns_av_unetI/netI     0.0431
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_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       -10
_diffrn_reflns_number            7245
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.006
_diffrn_reflns_theta_min         5.392
_exptl_absorpt_coefficient_mu    0.944
_exptl_absorpt_correction_T_max  0.2238
_exptl_absorpt_correction_T_min  0.1041
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1566 before and 0.0551 after correction.
The Ratio of minimum to maximum transmission is 0.4651.
The \l/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    1.503
_exptl_crystal_description       plate
_exptl_crystal_F_000             248
_exptl_crystal_recrystallization_method 'crystallsed from MeOH'
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     179
_refine_ls_number_reflns         1972
_refine_ls_number_restraints     11
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0427
_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/[\s^2^(Fo^2^)+(0.0746P)^2^+0.1667P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1127
_refine_ls_wR_factor_ref         0.1227
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1544
_reflns_number_total             1972
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ce01505f2.cif
_cod_data_source_block           cmpd5
_cod_depositor_comments
'Adding full bibliography for 7246127--7246132.cif.'
_cod_original_cell_volume        521.98(6)
_cod_database_code               7246127
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.972
_shelx_estimated_absorpt_t_min   0.848
_diffrn_measurement_ambient_temperature_device_make 'Oxford Crysostream 700'
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O2-H2A
 0.85 with sigma of 0.002
 N1-H1 \\sim N5-H5A \\sim N5-H5B \\sim N6-H6A \\sim N6-H6B
 with sigma of 0.002
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4)
3.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_shelx_res_checksum              87561
_olex2_submission_special_instructions 'No special instructions were received'