#------------------------------------------------------------------------------
#$Date: 2023-03-04 20:17:47 +0200 (Sat, 04 Mar 2023) $
#$Revision: 281445 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/61/7246128.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_7246128
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         'I, C8 H9 N6 O'
_chemical_formula_sum            'C8 H9 I N6 O'
_chemical_formula_weight         332.11
_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   geom
_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                115.810(1)
_cell_angle_beta                 99.266(2)
_cell_angle_gamma                97.192(2)
_cell_formula_units_Z            2
_cell_length_a                   7.8788(3)
_cell_length_b                   8.8064(3)
_cell_length_c                   8.8494(3)
_cell_measurement_reflns_used    5046
_cell_measurement_temperature    100
_cell_measurement_theta_max      71.910
_cell_measurement_theta_min      5.721
_cell_volume                     532.20(3)
_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 0.985
_diffrn_measured_fraction_theta_max 0.975
_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  0.0532
_diffrn_reflns_av_unetI/netI     0.0294
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2035
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         71.902
_diffrn_reflns_theta_min         5.720
_exptl_absorpt_coefficient_mu    23.588
_exptl_absorpt_correction_T_max  0.171059
_exptl_absorpt_correction_T_min  0.046858
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.
 
For component 1:
 wR2(int) was 0.1628 before and 0.0484 after correction.
 
For component 2:
 wR2(int) was 0.1726 before and 0.0521 after correction.
 The Ratio of minimum to maximum transmission is 0.23.

Final HKLF 4 output contains 19279 reflections, Rint = 0.0532
 (15507 with I > 3sig(I), Rint = 0.0511)
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.072
_exptl_crystal_description       plate
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.652
_refine_diff_density_min         -1.115
_refine_diff_density_rms         0.261
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.143
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2035
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.143
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0426
_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)+(0.0974P)²+0.2887P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1200
_refine_ls_wR_factor_ref         0.1217
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1999
_reflns_number_total             2035
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ce01505f2.cif
_cod_data_source_block           cmpd7
_cod_depositor_comments
'Adding full bibliography for 7246127--7246132.cif.'
_cod_database_code               7246128
_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   0.650
_shelx_estimated_absorpt_t_min   0.452
_diffrn_measurement_ambient_temperature_device_make 'Oxford Cryostream 700'
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.631(3)
 0.369(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C2(H2A), C4(H4), C5(H5)
3.b X=CH2 refined with riding coordinates:
 N5(H5A,H5B), N6(H6A,H6B)
;
_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
I1 I 0.73994(4) 0.06810(3) 0.88111(3) 0.01901(18) Uani 1 1 d . . . . .
O1 O 0.7328(5) 0.6372(5) 1.0163(5) 0.0211(8) Uani 1 1 d . . . . .
N1 N 0.5820(6) 0.3781(6) 0.7919(6) 0.0181(9) Uani 1 1 d . . . . .
H1 H 0.644727 0.325123 0.836724 0.022 Uiso 1 1 calc R U . . .
N2 N 0.2471(6) 0.7807(6) 0.6796(5) 0.0158(9) Uani 1 1 d . . . . .
H2 H 0.300905 0.834551 0.790204 0.019 Uiso 1 1 calc R U . . .
N3 N 0.0621(6) 0.7800(6) 0.4429(6) 0.0159(9) Uani 1 1 d . . . . .
N4 N 0.1723(6) 0.5282(6) 0.4170(6) 0.0170(9) Uani 1 1 d . . . . .
N5 N 0.1453(6) 1.0242(6) 0.7060(6) 0.0194(9) Uani 1 1 d . . . . .
H5A H 0.084187 1.078475 0.661634 0.023 Uiso 1 1 calc R U . . .
H5B H 0.203264 1.078177 0.815344 0.023 Uiso 1 1 calc R U . . .
N6 N -0.0220(6) 0.5221(6) 0.1923(6) 0.0180(9) Uani 1 1 d . . . . .
H6A H -0.088723 0.570274 0.144722 0.022 Uiso 1 1 calc R U . . .
H6B H -0.017557 0.413133 0.132303 0.022 Uiso 1 1 calc R U . . .
C1 C 0.6143(7) 0.5542(7) 0.8810(7) 0.0165(10) Uani 1 1 d . . . . .
C2 C 0.5004(7) 0.6330(7) 0.8053(6) 0.0162(10) Uani 1 1 d . . . . .
H2A H 0.513463 0.754965 0.861349 0.019 Uiso 1 1 calc R U . . .
C3 C 0.3742(7) 0.5340(7) 0.6543(7) 0.0162(10) Uani 1 1 d . . . . .
C4 C 0.3549(7) 0.3521(6) 0.5644(7) 0.0149(10) Uani 1 1 d . . . . .
H4 H 0.271858 0.284179 0.456338 0.018 Uiso 1 1 calc R U . . .
C5 C 0.4597(7) 0.2771(7) 0.6382(7) 0.0162(10) Uani 1 1 d . . . . .
H5 H 0.447585 0.155261 0.582837 0.019 Uiso 1 1 calc R U . . .
C6 C 0.2602(7) 0.6153(7) 0.5776(7) 0.0159(10) Uani 1 1 d . . . . .
C7 C 0.1499(7) 0.8616(7) 0.6083(7) 0.0175(10) Uani 1 1 d . . . . .
C8 C 0.0718(7) 0.6135(7) 0.3545(7) 0.0171(10) Uani 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'
I I -0.3257 6.8362 '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 N1 H1 117.4 . . ?
C1 N1 C5 125.2(5) . . ?
C5 N1 H1 117.4 . . ?
C6 N2 H2 120.3 . . ?
C7 N2 H2 120.3 . . ?
C7 N2 C6 119.4(5) . . ?
C7 N3 C8 115.7(5) . . ?
C6 N4 C8 116.2(5) . . ?
H5A N5 H5B 120.0 . . ?
C7 N5 H5A 120.0 . . ?
C7 N5 H5B 120.0 . . ?
H6A N6 H6B 120.0 . . ?
C8 N6 H6A 120.0 . . ?
C8 N6 H6B 120.0 . . ?
O1 C1 N1 121.4(5) . . ?
O1 C1 C2 123.9(5) . . ?
N1 C1 C2 114.7(5) . . ?
C1 C2 H2A 119.5 . . ?
C3 C2 C1 120.9(5) . . ?
C3 C2 H2A 119.5 . . ?
C2 C3 C4 121.0(5) . . ?
C2 C3 C6 120.6(5) . . ?
C4 C3 C6 118.4(5) . . ?
C3 C4 H4 121.0 . . ?
C5 C4 C3 118.0(5) . . ?
C5 C4 H4 121.0 . . ?
N1 C5 C4 120.0(5) . . ?
N1 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
N2 C6 C3 118.6(5) . . ?
N4 C6 N2 121.7(5) . . ?
N4 C6 C3 119.7(5) . . ?
N3 C7 N2 121.2(5) . . ?
N5 C7 N2 118.9(5) . . ?
N5 C7 N3 120.0(5) . . ?
N3 C8 N4 125.6(5) . . ?
N6 C8 N3 118.5(5) . . ?
N6 C8 N4 115.9(5) . . ?
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 1.244(7) . ?
N1 H1 0.8800 . ?
N1 C1 1.365(7) . ?
N1 C5 1.371(7) . ?
N2 H2 0.8800 . ?
N2 C6 1.368(7) . ?
N2 C7 1.366(7) . ?
N3 C7 1.331(7) . ?
N3 C8 1.347(7) . ?
N4 C6 1.299(7) . ?
N4 C8 1.367(7) . ?
N5 H5A 0.8800 . ?
N5 H5B 0.8800 . ?
N5 C7 1.321(7) . ?
N6 H6A 0.8800 . ?
N6 H6B 0.8800 . ?
N6 C8 1.325(7) . ?
C1 C2 1.450(7) . ?
C2 H2A 0.9500 . ?
C2 C3 1.369(7) . ?
C3 C4 1.419(7) . ?
C3 C6 1.472(7) . ?
C4 H4 0.9500 . ?
C4 C5 1.372(7) . ?
C5 H5 0.9500 . ?
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 N3 0.88 2.18 3.061(7) 178.4 2_576 yes
N5 H5B O1 0.88 2.22 2.828(6) 125.6 2_677 yes
N6 H6A O1 0.88 1.97 2.843(6) 169.7 1_454 yes
N6 H6B I1 0.88 3.02 3.736(4) 139.8 1_454 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 178.9(5) . . . . ?
N1 C1 C2 C3 -1.2(8) . . . . ?
C1 N1 C5 C4 -1.7(8) . . . . ?
C1 C2 C3 C4 -2.1(8) . . . . ?
C1 C2 C3 C6 -179.4(5) . . . . ?
C2 C3 C4 C5 3.6(8) . . . . ?
C2 C3 C6 N2 -18.0(8) . . . . ?
C2 C3 C6 N4 163.3(5) . . . . ?
C3 C4 C5 N1 -1.8(8) . . . . ?
C4 C3 C6 N2 164.6(5) . . . . ?
C4 C3 C6 N4 -14.1(8) . . . . ?
C5 N1 C1 O1 -177.0(5) . . . . ?
C5 N1 C1 C2 3.2(8) . . . . ?
C6 N2 C7 N3 2.6(8) . . . . ?
C6 N2 C7 N5 -176.7(5) . . . . ?
C6 N4 C8 N3 2.6(8) . . . . ?
C6 N4 C8 N6 -177.9(5) . . . . ?
C6 C3 C4 C5 -179.0(5) . . . . ?
C7 N2 C6 N4 -5.0(8) . . . . ?
C7 N2 C6 C3 176.4(5) . . . . ?
C7 N3 C8 N4 -4.8(8) . . . . ?
C7 N3 C8 N6 175.7(5) . . . . ?
C8 N3 C7 N2 2.0(7) . . . . ?
C8 N3 C7 N5 -178.8(5) . . . . ?
C8 N4 C6 N2 2.5(8) . . . . ?
C8 N4 C6 C3 -179.0(4) . . . . ?
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.631(3)
2 0.369(3)
