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_7059521
_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         'C23 H20 N6 O2, C3 H6 O'
_chemical_formula_sum            'C26 H26 N6 O3'
_chemical_formula_weight         470.53
_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   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                105.159(4)
_cell_angle_beta                 98.990(3)
_cell_angle_gamma                102.897(4)
_cell_formula_units_Z            2
_cell_length_a                   10.2690(4)
_cell_length_b                   10.7223(5)
_cell_length_c                   12.4618(5)
_cell_measurement_reflns_used    6946
_cell_measurement_temperature    293
_cell_measurement_theta_max      25.7740
_cell_measurement_theta_min      3.9100
_cell_volume                     1256.94(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)'
_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 0.984
_diffrn_measured_fraction_theta_max 0.811
_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    -83.00 -38.00   1.00   17.50    --   -7.78 153.00 -20.78   45
  2  \w    -16.00  79.00   1.00   17.50    --    8.41  77.00  60.00   95
  3  \w    -16.00  74.00   1.00   17.50    --    8.41  38.00 -30.00   90
  4  \w    -55.00  37.00   1.00   17.50    --    8.41 -57.00 150.00   92
  5  \w    -29.00  83.00   1.00   17.50    --    8.41  19.00-120.00  112
  6  \w    -37.00  42.00   1.00   17.50    --   10.00 -73.00-103.40   79
  7  \w      1.00  48.00   1.00   17.50    --   10.00 -91.00  14.66   47
;
_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      0.0393009000
_diffrn_orient_matrix_UB_12      -0.0291946000
_diffrn_orient_matrix_UB_13      -0.0361348000
_diffrn_orient_matrix_UB_21      0.0587665000
_diffrn_orient_matrix_UB_22      0.0544659000
_diffrn_orient_matrix_UB_23      0.0300381000
_diffrn_orient_matrix_UB_31      0.0172817000
_diffrn_orient_matrix_UB_32      -0.0356189000
_diffrn_orient_matrix_UB_33      0.0382144000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.811
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            18793
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.811
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.105
_diffrn_reflns_theta_min         3.009
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76152
_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    1.243
_exptl_crystal_description       prism
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.467
_refine_diff_density_min         -0.477
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.008(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/4 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     362
_refine_ls_number_reflns         5472
_refine_ls_number_restraints     84
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0850
_refine_ls_R_factor_gt           0.0641
_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^)+(0.0710P)^2^+0.7242P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1659
_refine_ls_wR_factor_ref         0.1803
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4065
_reflns_number_total             5472
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0nj01229g2.cif
_cod_data_source_block           mtf487
_cod_database_code               7059521
_shelx_shelxl_version_number     2016/4
_chemical_oxdiff_formula         'c23 h20 n6 o2'
_shelx_estimated_absorpt_t_max   0.994
_shelx_estimated_absorpt_t_min   0.975
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     24.66
_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
 At 1.5 times of:
  All C(H,H,H,H,H,H) groups
2. Restrained distances
 C18-C24
 1.39 with sigma of 0.01
 C24-C25
 1.39 with sigma of 0.01
 C25-C26
 1.39 with sigma of 0.01
 C26-C27
 1.39 with sigma of 0.01
 C27-C28
 1.39 with sigma of 0.01
 C28-C18
 1.39 with sigma of 0.01
 C29-O3
 1.2 with sigma of 0.005
 C30-O4
 1.2 with sigma of 0.005
 C29-C31
 1.45 with sigma of 0.005
 C29-C32
 1.45 with sigma of 0.005
 C30-C32
 1.45 with sigma of 0.005
 C30-C31
 1.45 with sigma of 0.005
3. Uiso/Uaniso restraints and constraints
Uanis(C29) = Uanis(C30)
4. Rigid body (RIGU) restrains
 C18, C19, C20, C21, C22, C23
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C18, C24, C25, C26, C27, C28
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
5. Others
 Fixed Sof: C19(0.5) H19(0.5) C20(0.5) H20(0.5) C21(0.5) H21(0.5) C22(0.5)
 H22(0.5) C23(0.5) H23(0.5) C24(0.5) H24(0.5) C25(0.5) H25(0.5) C26(0.5)
 H26(0.5) C27(0.5) H27(0.5) C28(0.5) H28(0.5) O3(0.75) O4(0.25) C29(0.75)
 C30(0.25) H31A(0.75) H31B(0.75) H31C(0.75) H31D(0.25) H31E(0.25) H31F(0.25)
 H32A(0.75) H32B(0.75) H32C(0.75) H32D(0.25) H32E(0.25) H32F(0.25)
6.a Riding coordinates:
 N4(H4A,H4B)
6.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C17(H17A,H17B)
6.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C5(H5), C6(H6), C7(H7), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25),
  C26(H26), C27(H27), C28(H28)
6.d Fitted hexagon refined as free rotating group:
 C18(C19,C20,C21,C22,C23)
6.e Idealised Me refined with riding coordinates:
 C31(H31A,H31B,H31C), C31(H31D,H31E,H31F), C32(H32A,H32B,H32C), C32(H32D,H32E,
 H32F)
;
_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 1.432
_oxdiff_exptl_absorpt_empirical_full_min 0.591