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_7059518
_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         'C9 H7 N3 O2'
_chemical_formula_sum            'C9 H7 N3 O2'
_chemical_formula_weight         189.18
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_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                 107.776(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.5711(7)
_cell_length_b                   10.4626(6)
_cell_length_c                   7.7586(6)
_cell_measurement_reflns_used    3789
_cell_measurement_temperature    293
_cell_measurement_theta_max      70.9620
_cell_measurement_theta_min      6.1190
_cell_volume                     817.14(10)
_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)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.992
_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    -68.00 -41.00   1.00    5.00    --  -41.07 -77.00 -60.00   27
  2  \w    -56.00 -18.00   1.00    5.00    --  -41.07 -38.00 -30.00   38
  3  \w   -117.00 -10.00   1.00    5.00    --  -41.07 -77.00 -30.00  107
  4  \w   -112.00 -61.00   1.00    5.00    --  -41.07 -57.00-150.00   51
  5  \w    -50.00 -25.00   1.00    5.00    --  -41.07 -57.00 -90.00   25
  6  \w   -117.00 -86.00   1.00    5.00    --  -41.07 -77.00 -60.00   31
  7  \w    -42.00 -16.00   1.00    5.00    --  -41.07 -57.00-150.00   26
  8  \w      5.00  71.00   1.00    5.00    --   41.07 -99.00-180.00   66
  9  \w      3.00  60.00   1.00    5.00    --   41.07 -99.00  60.00   57
 10  \w    110.00 177.00   1.00   20.00    --  101.41  77.00 -90.00   67
 11  \w    109.00 168.00   1.00   20.00    --  101.41  30.00  90.00   59
 12  \w     77.00 169.00   1.00   20.00    --  101.41  45.00 -30.00   92
 13  \w     73.00  98.00   1.00   20.00    --  101.41  61.00   0.00   25
 14  \w     98.00 123.00   1.00   20.00    --  101.41 125.00  90.00   25
 15  \w     69.00  95.00   1.00   20.00    --  101.41  77.00 -60.00   26
 16  \w     70.00  95.00   1.00   20.00    --  101.41  77.00 -90.00   25
 17  \w     30.00 129.00   1.00   20.00    --  101.41 -61.00 150.00   99
 18  \w     69.00 157.00   1.00   20.00    --  101.41  77.00  30.00   88
 19  \w     68.00  95.00   1.00   20.00    --  101.41 -94.00-120.00   27
 20  \w     69.00  95.00   1.00   20.00    --  101.41  77.00   0.00   26
 21  \w     73.00  98.00   1.00   20.00    --  101.41  61.00 -30.00   25
 22  \w     72.00  98.00   1.00   20.00    --  101.41  61.00 -90.00   26
 23  \w     70.00  95.00   1.00   20.00    --  101.41  77.00 -30.00   25
 24  \w     81.00 171.00   1.00   20.00    --  101.41  45.00   0.00   90
 25  \w     77.00 102.00   1.00   20.00    --  101.41  45.00  30.00   25
 26  \w     77.00 102.00   1.00   20.00    --  101.41  45.00 -60.00   25
 27  \w     73.00  98.00   1.00   20.00    --  101.41  61.00 -60.00   25
 28  \w    149.00 175.00   1.00   20.00    --  101.41 125.00  90.00   26
 29  \w     72.00  99.00   1.00   20.00    --  101.41  61.00  30.00   27
 30  \w     28.00 120.00   1.00   20.00    --  101.41 -45.00-120.00   92
;
_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      -0.1148208000
_diffrn_orient_matrix_UB_12      -0.0499223000
_diffrn_orient_matrix_UB_13      -0.1605579000
_diffrn_orient_matrix_UB_21      0.0867600000
_diffrn_orient_matrix_UB_22      0.0162018000
_diffrn_orient_matrix_UB_23      -0.1260703000
_diffrn_orient_matrix_UB_31      0.0517730000
_diffrn_orient_matrix_UB_32      -0.1375471000
_diffrn_orient_matrix_UB_33      0.0432465000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_unetI/netI     0.0070
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            2839
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.828
_diffrn_reflns_theta_min         4.392
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.950
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91531
_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    1.538
_exptl_crystal_description       prism
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         2839
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_gt           0.0409
_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^)+(0.0650P)^2^+0.1282P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1157
_refine_ls_wR_factor_ref         0.1181
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2470
_reflns_number_total             2839
_reflns_threshold_expression     'I > 2\s(I)'
_twin_special_details
;
Component 2 rotated by -179.9916\% 
 around [1.00 0.00 0.00] (reciprocal) or [0.92 0.00 0.38] (direct)
;
_cod_data_source_file            d0nj01229g2.cif
_cod_data_source_block           mtf467_hklf5
_cod_database_code               7059518
_shelx_shelxl_version_number     2016/4
_chemical_oxdiff_formula         'c9 h7 n3 o2'
_shelx_estimated_absorpt_t_max   0.928
_shelx_estimated_absorpt_t_min   0.833
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.5650(17)
 0.4350(17)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
3.a Riding coordinates:
 N3(H3A,H3B)
3.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C4(H4), C5(H5), C6(H6), C7(H7)
;
_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 1.316
_oxdiff_exptl_absorpt_empirical_full_min 0.798
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2