Construction of 1,2-dihydro-1,3,5-triazines <i>via</i> reactions involving amidines.
Guo, Honghong; Lin, Jianying; Liu, Qiang; Li, Xing; Organic & biomolecular chemistry 21 (2023) 4269–4275; doi:10.1039/d3ob00283g

data_7159343
_publ_section_title
;
 Construction of 1,2-dihydro-1,3,5-triazines <i>via</i> reactions
 involving amidines.
;
_journal_issue                   20
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4269
_journal_page_last               4275
_journal_paper_doi               10.1039/d3ob00283g
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C27 H19 F2 N3'
_chemical_formula_sum            'C27 H19 F2 N3'
_chemical_formula_weight         423.45
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2022-10-12
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2018.12.18 svn.r3554 for Rigaku Oxford Diffraction, GUI svn.r1)
;
_audit_update_record
;
2022-12-06 deposited with the CCDC.	2023-04-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.307(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.1865(2)
_cell_length_b                   11.3004(2)
_cell_length_c                   19.1635(4)
_cell_measurement_reflns_used    5785
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.0480
_cell_measurement_theta_min      4.5520
_cell_volume                     2146.71(7)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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 (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.977
_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   -102.00 -13.00   1.00    1.00    --  -35.62 147.00  11.00   89
  2  \w    -69.00 -44.00   1.00    1.00    --  -35.62 124.00-153.00   25
  3  \w     31.00  56.00   1.00    1.00    --   35.62-124.00 127.00   25
  4  \w    103.00 128.00   1.00    1.24    --  107.12 147.00  11.00   25
  5  \w     42.00 115.00   1.00    1.24    --  107.12-124.00 127.00   73
  6  \w    111.00 136.00   1.00    1.24    --  107.12 124.00-153.00   25
  7  \w     86.00 113.00   1.00    1.24    --  107.12-147.00 -37.00   27
  8  \w    -93.00 -40.00   1.00    1.00    --  -35.62 178.00-120.00   53
  9  \w   -102.00 -20.00   1.00    1.00    --  -35.62 -57.00 -90.00   82
 10  \w     20.00  99.00   1.00    1.00    --   35.62  57.00  30.00   79
 11  \w     24.00  72.00   1.00    1.00    --   35.62 -99.00 -60.00   48
 12  \w     81.00 106.00   1.00    1.24    --  107.12 -95.00   0.00   25
 13  \w     49.00  80.00   1.00    1.24    --  107.12 -95.00 -30.00   31
 14  \w    119.00 174.00   1.00    1.24    --  107.12  45.00-150.00   55
 15  \w     90.00 176.00   1.00    1.24    --  107.12  45.00   0.00   86
 16  \w     48.00 110.00   1.00    1.24    --  107.12 -95.00 150.00   62
 17  \w    100.00 175.00   1.00    1.24    --  107.12 111.00  30.00   75
 18  \w    102.00 167.00   1.00    1.24    --  107.12 111.00 150.00   65
 19  \w    133.00 169.00   1.00    1.24    --  107.12 111.00  60.00   36
 20  \w    103.00 128.00   1.00    1.24    --  107.12  61.00 -60.00   25
 21  \w     37.00 120.00   1.00    1.24    --  107.12 -30.00  60.00   83
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0315789000
_diffrn_orient_matrix_UB_12      -0.1329409000
_diffrn_orient_matrix_UB_13      -0.0117631000
_diffrn_orient_matrix_UB_21      -0.1040308000
_diffrn_orient_matrix_UB_22      0.0286884000
_diffrn_orient_matrix_UB_23      -0.0699740000
_diffrn_orient_matrix_UB_31      0.1109060000
_diffrn_orient_matrix_UB_32      -0.0108180000
_diffrn_orient_matrix_UB_33      -0.0423053000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            10518
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.497
_diffrn_reflns_theta_min         4.544
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.737
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74233
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_F_000             880
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.414
_refine_diff_density_rms         0.097
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         4088
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0638
_refine_ls_R_factor_gt           0.0578
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0803P)^2^+0.4810P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1521
_refine_ls_wR_factor_ref         0.1584
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3534
_reflns_number_total             4088
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00283g2.cif
_cod_data_source_block           yhb-2-20221012
_cod_depositor_comments
'Adding full bibliography for 7159343--7159344.cif.'
_cod_database_code               7159343
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C1 H1 F1 N1 O1'
_diffrn_oxdiff_digest_frames
;
01473b9dfc98ce9f966b3a0889676fd31800030107c
;
_diffrn_oxdiff_digest_hkl
;
01a56ec8086894cece25038b96f5cc11f59884
;
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6)
2.b Aromatic/amide H refined with riding coordinates:
 C14(H14), C8(H8), C25(H25), C12(H12), C21(H21), C23(H23), C32(H32), C18(H18),
 C28(H28), C22(H22), C16(H16), C17(H17), C11(H11), C9(H9), C10(H10), C31(H31),
 C29(H29), C30(H30)
;
_shelx_res_checksum              35260
_olex2_date_sample_data_collection 2022-10-12
_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 2.151
_oxdiff_exptl_absorpt_empirical_full_min 0.493