Synthesis and Characterization of new Heterocycles related to Aryl[e][1,3]diazepinediones. Rearrangement to 2,4-Diamino-1,3,5-triazine Derivatives.
Bardovskyi, Rostyslav; Grytsai, Oleksandr; RONCO, Cyril; Benhida, Rachid; New Journal of Chemistry 44 (2020) 8171–8175; doi:10.1039/D0NJ01229G

data_7059519
_publ_section_title
;
 Synthesis and Characterization of new Heterocycles related to
 Aryl[e][1,3]diazepinediones. Rearrangement to 2,4-Diamino-1,3,5-triazine
 Derivatives.
;
_journal_issue                   20
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              8171
_journal_page_last               8175
_journal_paper_doi               10.1039/D0NJ01229G
_journal_volume                  44
_journal_year                    2020
_chemical_formula_moiety         'C12 H13 N5 O2'
_chemical_formula_sum            'C12 H13 N5 O2'
_chemical_formula_weight         259.27
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2018-06-01
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3510 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-02-07 deposited with the CCDC.	2020-04-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.7280(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.86080(10)
_cell_length_b                   24.6111(3)
_cell_length_c                   10.3984(2)
_cell_measurement_reflns_used    5652
_cell_measurement_temperature    293
_cell_measurement_theta_max      70.9170
_cell_measurement_theta_min      4.6770
_cell_volume                     1217.99(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.44a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.44a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.44a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w   -108.00 -13.00   1.00    1.00    --  -41.07 -57.00 -90.00   95
  2  \w    -53.00 -27.00   1.00    1.00    --  -41.07 -38.00 -60.00   26
  3  \w    -66.00  15.00   1.00    1.00    --  -41.07  38.00 -30.00   81
  4  \w    -72.00   2.00   1.00    1.00    --  -41.07  77.00 120.00   74
  5  \w    -83.00 -17.00   1.00    1.00    --  -41.07 -38.00  90.00   66
  6  \w     52.00 108.00   1.00   10.00    --  101.41 -94.00  60.00   56
  7  \w     83.00 110.00   1.00   10.00    --  101.41-125.00  30.00   27
  8  \w     68.00 127.00   1.00   10.00    --  101.41 -61.00-120.00   59
  9  \w     28.00  54.00   1.00   10.00    --  101.41-125.00  30.00   26
 10  \w     38.00 127.00   1.00   10.00    --  101.41 -45.00  60.00   89
 11  \w     33.00 128.00   1.00   10.00    --  101.41 -30.00-180.00   95
 12  \w    122.00 166.00   1.00   10.00    --  101.41  45.00   0.00   44
 13  \w     69.00 125.00   1.00   10.00    --  101.41  77.00 -30.00   56
 14  \w    153.00 178.00   1.00   10.00    --  101.41  77.00 -30.00   25
 15  \w     49.00 101.00   1.00   10.00    --  101.41 -94.00-180.00   52
 16  \w    135.00 175.00   1.00   10.00    --  101.41 125.00  30.00   40
 17  \w    120.00 165.00   1.00   10.00    --  101.41 125.00 120.00   45
 18  \w     25.00 115.00   1.00   10.00    --  101.41 -30.00 -30.00   90
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0776656000
_diffrn_orient_matrix_UB_12      -0.0502980000
_diffrn_orient_matrix_UB_13      0.0880800000
_diffrn_orient_matrix_UB_21      0.0139819000
_diffrn_orient_matrix_UB_22      0.0356394000
_diffrn_orient_matrix_UB_23      0.1229225000
_diffrn_orient_matrix_UB_31      -0.3139979000
_diffrn_orient_matrix_UB_32      -0.0108555000
_diffrn_orient_matrix_UB_33      -0.0044416000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0120
_diffrn_reflns_av_unetI/netI     0.0101
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7754
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.052
_diffrn_reflns_theta_min         3.592
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.841
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90097
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.44a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_description       prism
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.374
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2295
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0407
_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/[\s^2^(Fo^2^)+(0.0605P)^2^+0.3373P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1071
_refine_ls_wR_factor_ref         0.1082
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2191
_reflns_number_total             2295
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0nj01229g2.cif
_cod_data_source_block           mtf478
_cod_database_code               7059519
_shelx_shelxl_version_number     2016/4
_chemical_oxdiff_formula         'c12 h13 n5 o2'
_shelx_estimated_absorpt_t_max   0.936
_shelx_estimated_absorpt_t_min   0.824
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C5(H5), C6(H6), C7(H7), C8(H8)
2.b X=CH2 refined with riding coordinates:
 N4(H4A,H4B)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.176
_oxdiff_exptl_absorpt_empirical_full_min 0.727