#------------------------------------------------------------------------------
#$Date: 2023-03-04 20:17:47 +0200 (Sat, 04 Mar 2023) $
#$Revision: 281445 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/61/7246131.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_7246131
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         '2(C11 H14 N6 O2), 3(H2 O)'
_chemical_formula_sum            'C22 H34 N12 O7'
_chemical_formula_weight         578.61
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 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                90
_cell_angle_beta                 93.4284(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.8893(1)
_cell_length_b                   18.4452(2)
_cell_length_c                   12.5023(1)
_cell_measurement_reflns_used    9977
_cell_measurement_temperature    100
_cell_measurement_theta_max      71.385
_cell_measurement_theta_min      4.430
_cell_volume                     2736.85(4)
_computing_cell_refinement
;
SAINT (2013) V8.38A; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_collection
;
APEX 2 (2013) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction
;
SAINT (2013) V8.38A; 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 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker Smart APEX'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 'Hampton Research Cryoloop'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0191
_diffrn_reflns_av_unetI/netI     0.0113
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            32901
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         71.378
_diffrn_reflns_theta_min         4.430
_exptl_absorpt_coefficient_mu    0.907
_exptl_absorpt_correction_T_max  0.7535
_exptl_absorpt_correction_T_min  0.6823
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1021 before and 0.0318 after correction.
The Ratio of minimum to maximum transmission is 0.9055.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_description       prism
_exptl_crystal_F_000             1224
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     215
_refine_ls_number_reflns         2666
_refine_ls_number_restraints     9
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0381
_refine_ls_R_factor_gt           0.0374
_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)+(0.0606P)²+1.7593P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0987
_refine_ls_wR_factor_ref         0.0998
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2607
_reflns_number_total             2666
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ce01505f2.cif
_cod_data_source_block           cmpd3
_cod_depositor_comments
'Adding full bibliography for 7246127--7246132.cif.'
_cod_database_code               7246131
_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   0.891
_shelx_estimated_absorpt_t_min   0.798
_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. Restrained distances
 N5-H5A \\sim N5-H5B \\sim N6-H6A \\sim N6-H6B
 with sigma of 0.02
 O3-H3A \\sim O4-H4A \\sim O4-H4B
 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4)
3.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+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_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 0.84734(6) 0.55494(4) 0.45331(6) 0.0183(2) Uani 1 1 d . . . . .
O2 O 1.06845(7) 0.68712(5) 0.45820(7) 0.0270(2) Uani 1 1 d . . . . .
N1 N 0.83522(7) 0.50472(5) 0.62177(7) 0.0163(2) Uani 1 1 d . . . . .
N2 N 0.49594(7) 0.40342(5) 0.40948(7) 0.0147(2) Uani 1 1 d . . . . .
N3 N 0.34157(7) 0.32623(5) 0.44976(7) 0.0165(2) Uani 1 1 d . . . . .
N4 N 0.48114(8) 0.35907(5) 0.58740(7) 0.0182(2) Uani 1 1 d . . . . .
N5 N 0.35726(7) 0.37334(5) 0.28121(7) 0.0170(2) Uani 1 1 d D . . . .
H5A H 0.3942(11) 0.3968(7) 0.2336(10) 0.020(3) Uiso 1 1 d D . . . .
H5B H 0.2941(11) 0.3513(7) 0.2601(11) 0.022(3) Uiso 1 1 d D . . . .
N6 N 0.33717(8) 0.28119(6) 0.62115(8) 0.0217(2) Uani 1 1 d D . . . .
H6A H 0.3723(11) 0.2733(8) 0.6840(10) 0.021(3) Uiso 1 1 d D . . . .
H6B H 0.2817(11) 0.2511(8) 0.5993(11) 0.025(4) Uiso 1 1 d D . . . .
C1 C 0.79316(9) 0.51205(6) 0.52203(8) 0.0149(2) Uani 1 1 d . . . . .
C2 C 0.69456(9) 0.47803(6) 0.48098(8) 0.0156(2) Uani 1 1 d . . . . .
H2 H 0.668268 0.484307 0.408315 0.019 Uiso 1 1 calc R U . . .
C3 C 0.77675(9) 0.46284(6) 0.68785(8) 0.0184(2) Uani 1 1 d . . . . .
H3 H 0.805257 0.457513 0.760038 0.022 Uiso 1 1 calc R U . . .
C4 C 0.67861(9) 0.42762(6) 0.65644(8) 0.0180(2) Uani 1 1 d . . . . .
H4 H 0.640025 0.398982 0.705697 0.022 Uiso 1 1 calc R U . . .
C5 C 0.63671(9) 0.43501(6) 0.54964(8) 0.0152(2) Uani 1 1 d . . . . .
C6 C 0.53034(9) 0.39686(5) 0.51269(8) 0.0147(2) Uani 1 1 d . . . . .
C7 C 0.39831(8) 0.36756(5) 0.38265(8) 0.0148(2) Uani 1 1 d . . . . .
C8 C 0.38747(9) 0.32293(6) 0.55091(8) 0.0168(2) Uani 1 1 d . . . . .
C9 C 0.93730(9) 0.59882(6) 0.50013(8) 0.0170(2) Uani 1 1 d . . . . .
H9A H 0.999118 0.567786 0.530667 0.020 Uiso 1 1 calc R U . . .
H9B H 0.909711 0.629482 0.558047 0.020 Uiso 1 1 calc R U . . .
C10 C 0.97832(9) 0.64548(6) 0.41127(8) 0.0188(2) Uani 1 1 d . . . . .
H10A H 1.004576 0.614944 0.352596 0.023 Uiso 1 1 calc R U . . .
H10B H 0.917181 0.677474 0.381835 0.023 Uiso 1 1 calc R U . . .
C11 C 1.12030(10) 0.73100(7) 0.38197(10) 0.0252(3) Uani 1 1 d . . . . .
H11A H 1.159285 0.700022 0.332365 0.038 Uiso 1 1 calc R U . . .
H11B H 1.174757 0.763611 0.419080 0.038 Uiso 1 1 calc R U . . .
H11C H 1.062648 0.759678 0.341813 0.038 Uiso 1 1 calc R U . . .
O3 O 1.000000 0.57741(6) 0.750000 0.0202(2) Uani 1 2 d DS T P . .
H3A H 0.9552(14) 0.5505(9) 0.7080(13) 0.044(5) Uiso 1 1 d D . . . .
O4 O 1.13952(7) 0.68728(5) 0.68504(7) 0.0232(2) Uani 1 1 d D . . . .
H4A H 1.1209(15) 0.6937(10) 0.6172(12) 0.044(5) Uiso 1 1 d D . . . .
H4B H 1.0946(14) 0.6529(9) 0.7022(13) 0.038(4) Uiso 1 1 d 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 116.08(8) . . ?
C10 O2 C11 112.29(8) . . ?
C1 N1 C3 117.06(9) . . ?
C6 N2 C7 113.68(9) . . ?
C7 N3 C8 114.89(9) . . ?
C6 N4 C8 114.16(9) . . ?
H5A N5 H5B 118.6(13) . . ?
C7 N5 H5A 121.0(9) . . ?
C7 N5 H5B 120.3(9) . . ?
H6A N6 H6B 118.3(13) . . ?
C8 N6 H6A 118.3(9) . . ?
C8 N6 H6B 120.6(9) . . ?
O1 C1 C2 116.59(9) . . ?
N1 C1 O1 119.28(9) . . ?
N1 C1 C2 124.13(10) . . ?
C1 C2 H2 121.1 . . ?
C5 C2 C1 117.81(9) . . ?
C5 C2 H2 121.1 . . ?
N1 C3 H3 118.2 . . ?
N1 C3 C4 123.69(10) . . ?
C4 C3 H3 118.2 . . ?
C3 C4 H4 120.9 . . ?
C3 C4 C5 118.27(10) . . ?
C5 C4 H4 120.9 . . ?
C2 C5 C4 119.02(10) . . ?
C2 C5 C6 121.41(9) . . ?
C4 C5 C6 119.57(9) . . ?
N2 C6 C5 117.39(9) . . ?
N4 C6 N2 127.18(9) . . ?
N4 C6 C5 115.42(9) . . ?
N3 C7 N2 125.05(10) . . ?
N5 C7 N2 116.95(9) . . ?
N5 C7 N3 117.99(9) . . ?
N3 C8 N4 124.93(10) . . ?
N6 C8 N3 118.07(10) . . ?
N6 C8 N4 117.00(10) . . ?
O1 C9 H9A 110.4 . . ?
O1 C9 H9B 110.4 . . ?
O1 C9 C10 106.65(8) . . ?
H9A C9 H9B 108.6 . . ?
C10 C9 H9A 110.4 . . ?
C10 C9 H9B 110.4 . . ?
O2 C10 C9 105.90(8) . . ?
O2 C10 H10A 110.6 . . ?
O2 C10 H10B 110.6 . . ?
C9 C10 H10A 110.6 . . ?
C9 C10 H10B 110.6 . . ?
H10A C10 H10B 108.7 . . ?
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 H3A 111(2) . 2_756 ?
H4A O4 H4B 102.5(16) . . ?
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 1.3584(13) . ?
O1 C9 1.4377(12) . ?
O2 C10 1.4168(13) . ?
O2 C11 1.4190(13) . ?
N1 C1 1.3224(14) . ?
N1 C3 1.3533(14) . ?
N2 C6 1.3356(13) . ?
N2 C7 1.3605(14) . ?
N3 C7 1.3445(14) . ?
N3 C8 1.3483(14) . ?
N4 C6 1.3288(14) . ?
N4 C8 1.3534(14) . ?
N5 H5A 0.876(12) . ?
N5 H5B 0.881(12) . ?
N5 C7 1.3357(14) . ?
N6 H6A 0.879(12) . ?
N6 H6B 0.892(12) . ?
N6 C8 1.3358(14) . ?
C1 C2 1.3998(15) . ?
C2 H2 0.9500 . ?
C2 C5 1.3821(15) . ?
C3 H3 0.9500 . ?
C3 C4 1.3722(15) . ?
C4 H4 0.9500 . ?
C4 C5 1.4035(15) . ?
C5 C6 1.4960(14) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.5092(14) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
O3 H3A 0.879(14) . ?
O3 H3A 0.879(14) 2_756 ?
O4 H4A 0.872(15) . ?
O4 H4B 0.864(14) . ?
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 N2 0.876(12) 2.280(12) 3.0880(12) 153.4(12) 2_655 yes
N5 H5B O4 0.881(12) 2.135(12) 3.0041(12) 169.1(13) 6_465 yes
N6 H6A O4 0.879(12) 2.291(13) 2.9780(13) 134.9(12) 4_646 yes
N6 H6B N3 0.892(12) 2.110(13) 3.0005(13) 175.9(14) 7_556 yes
O3 H3A N1 0.879(14) 1.930(14) 2.7983(10) 169.1(17) . yes
O4 H4A O2 0.872(15) 2.051(15) 2.9105(12) 168.4(17) . yes
O4 H4B O3 0.864(14) 1.908(14) 2.7711(12) 176.0(16) . 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 C5 -178.97(9) . . . . ?
O1 C9 C10 O2 -178.72(8) . . . . ?
N1 C1 C2 C5 1.07(16) . . . . ?
N1 C3 C4 C5 0.41(16) . . . . ?
C1 O1 C9 C10 -175.72(8) . . . . ?
C1 N1 C3 C4 0.83(16) . . . . ?
C1 C2 C5 C4 0.25(15) . . . . ?
C1 C2 C5 C6 179.75(9) . . . . ?
C2 C5 C6 N2 2.83(15) . . . . ?
C2 C5 C6 N4 -177.98(9) . . . . ?
C3 N1 C1 O1 178.45(9) . . . . ?
C3 N1 C1 C2 -1.59(15) . . . . ?
C3 C4 C5 C2 -0.93(15) . . . . ?
C3 C4 C5 C6 179.56(9) . . . . ?
C4 C5 C6 N2 -177.67(9) . . . . ?
C4 C5 C6 N4 1.52(14) . . . . ?
C6 N2 C7 N3 -2.79(14) . . . . ?
C6 N2 C7 N5 178.27(9) . . . . ?
C6 N4 C8 N3 -3.28(16) . . . . ?
C6 N4 C8 N6 176.94(9) . . . . ?
C7 N2 C6 N4 1.35(15) . . . . ?
C7 N2 C6 C5 -179.57(8) . . . . ?
C7 N3 C8 N4 2.05(15) . . . . ?
C7 N3 C8 N6 -178.17(9) . . . . ?
C8 N3 C7 N2 1.23(15) . . . . ?
C8 N3 C7 N5 -179.84(9) . . . . ?
C8 N4 C6 N2 1.45(16) . . . . ?
C8 N4 C6 C5 -177.65(9) . . . . ?
C9 O1 C1 N1 -9.94(14) . . . . ?
C9 O1 C1 C2 170.10(9) . . . . ?
C11 O2 C10 C9 176.53(9) . . . . ?
