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_7059520
_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         'C15 H17 N5 O2'
_chemical_formula_sum            'C15 H17 N5 O2'
_chemical_formula_weight         299.33
_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
_audit_creation_date             2018-05-29
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_audit_update_record
;
2020-02-07 deposited with the CCDC.	2020-04-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.554(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   24.9167(6)
_cell_length_b                   7.5596(2)
_cell_length_c                   15.5987(4)
_cell_measurement_reflns_used    6579
_cell_measurement_temperature    293
_cell_measurement_theta_max      70.8800
_cell_measurement_theta_min      3.5820
_cell_volume                     2897.42(13)
_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 0.997
_diffrn_measured_fraction_theta_max 0.983
_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    -67.00  -8.00   1.00    5.00    --  -41.07 -77.00-180.00   59
  2  \w    -79.00 -40.00   1.00    5.00    --  -41.07 -57.00-180.00   39
  3  \w   -129.00  47.00   1.00    5.00    --  -41.07   0.00 -60.00  176
  4  \w    -69.00 -15.00   1.00    5.00    --  -41.07 -57.00-120.00   54
  5  \w    -50.00 -25.00   1.00    5.00    --  -41.07 -38.00 150.00   25
  6  \w     48.00  83.00   1.00    5.00    --   41.07-125.00-180.00   35
  7  \w     70.00  95.00   1.00   20.00    --  101.41  77.00-120.00   25
  8  \w    116.00 177.00   1.00   20.00    --  101.41  77.00-150.00   61
  9  \w    115.00 172.00   1.00   20.00    --  101.41  45.00 -60.00   57
 10  \w     48.00  93.00   1.00   20.00    --  101.41 -94.00-150.00   45
 11  \w     72.00  99.00   1.00   20.00    --  101.41  61.00 150.00   27
 12  \w     77.00 102.00   1.00   20.00    --  101.41  45.00-120.00   25
 13  \w     69.00  95.00   1.00   20.00    --  101.41  77.00-180.00   26
 14  \w    107.00 172.00   1.00   20.00    --  101.41  77.00-180.00   65
 15  \w    108.00 140.00   1.00   20.00    --  101.41  77.00 150.00   32
 16  \w     70.00  95.00   1.00   20.00    --  101.41  77.00-150.00   25
 17  \w     73.00 108.00   1.00   20.00    --  101.41  61.00-120.00   35
 18  \w     30.00 129.00   1.00   20.00    --  101.41 -61.00-120.00   99
 19  \w     72.00 117.00   1.00   20.00    --  101.41  61.00-180.00   45
 20  \w     74.00 101.00   1.00   20.00    --  101.41  61.00-150.00   27
 21  \w     74.00 101.00   1.00   20.00    --  101.41  61.00 -90.00   27
 22  \w     69.00  95.00   1.00   20.00    --  101.41  77.00 150.00   26
 23  \w    152.00 178.00   1.00   20.00    --  101.41  77.00 -90.00   26
 24  \w     70.00 108.00   1.00   20.00    --  101.41  77.00 -90.00   38
 25  \w    108.00 177.00   1.00   20.00    --  101.41  77.00-120.00   69
 26  \w     79.00 106.00   1.00   20.00    --  101.41  45.00 -90.00   27
 27  \w     76.00 103.00   1.00   20.00    --  101.41  45.00-150.00   27
 28  \w     19.00 101.00   1.00   20.00    --  101.41 -94.00  30.00   82
;
_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      0.0557729000
_diffrn_orient_matrix_UB_12      0.0406915000
_diffrn_orient_matrix_UB_13      -0.0257954000
_diffrn_orient_matrix_UB_21      0.0235106000
_diffrn_orient_matrix_UB_22      0.0390336000
_diffrn_orient_matrix_UB_23      0.0957560000
_diffrn_orient_matrix_UB_31      0.0163166000
_diffrn_orient_matrix_UB_32      -0.1959091000
_diffrn_orient_matrix_UB_33      0.0138049000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0216
_diffrn_reflns_av_unetI/netI     0.0149
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11000
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.136
_diffrn_reflns_theta_min         3.598
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.782
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72426
_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    1.372
_exptl_crystal_description       prism
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2758
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0387
_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^)+(0.0474P)^2^+1.7395P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0993
_refine_ls_wR_factor_ref         0.1021
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2510
_reflns_number_total             2758
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0nj01229g2.cif
_cod_data_source_block           mtf483
_cod_database_code               7059520
_shelx_shelxl_version_number     2016/4
_shelx_estimated_absorpt_t_max   0.926
_shelx_estimated_absorpt_t_min   0.788
_reflns_odcompleteness_completeness 99.74
_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 C(H,H) groups, All N(H) groups, All N(H,H) groups
2.a Riding coordinates:
 N4(H4A,H4B)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C5(H5), C6(H6), C7(H7), C8(H8)
;
_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 2.048
_oxdiff_exptl_absorpt_empirical_full_min 0.709