Visible-light-Catalyzed [3 + 1 + 2] Coupling Annulations for the Synthesis of Unsymmetrical Tri-substituted Amino-1,3,5-triazines.
Guo, Wei; Zhao, Mingming; Chengtang, Du; Zheng, Lvyin; Li, Luo; Chen, Liping; Tao, Kailiang; Tan, Wen; Xie, Zhen; Cai, Liuhuan; Fan, XiaoLin; Zhang, Kai; The Journal of organic chemistry  (2019) –; doi:10.1021/acs.joc.9b02514

data_4036059
_publ_section_title
;
 Visible-light-Catalyzed [3 + 1 + 2] Coupling Annulations for the
 Synthesis of Unsymmetrical Tri-substituted Amino-1,3,5-triazines.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b02514
_journal_year                    2019
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C18 H19 N5 O'
_chemical_formula_sum            'C18 H19 N5 O'
_chemical_formula_weight         321.38
_space_group_crystal_system      orthorhombic
_space_group_IT_number           37
_space_group_name_Hall           'C 2 -2c'
_space_group_name_H-M_alt        'C c c 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2019-03-14
_audit_creation_method
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   16.55068(10)
_cell_length_b                   26.78093(17)
_cell_length_c                   7.26499(5)
_cell_measurement_reflns_used    19424
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      73.2520
_cell_measurement_theta_min      5.3130
_cell_volume                     3220.15(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2913
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_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    -61.00 -31.00   1.00    1.00    --  -41.14  77.00   0.00   30
  2  \w    -68.00  32.00   1.00    1.00    --  -41.14  77.00-120.00  100
  3  \w    -14.00  33.00   1.00    1.00    --  -41.14  77.00   0.00   47
  4  \w     88.00 176.00   1.00    1.00    --  106.22  77.00  30.00   88
  5  \w     95.00 171.00   1.00    1.00    --  106.22  77.00-180.00   76
  6  \w    146.00 172.00   1.00    1.00    --  106.22  77.00-150.00   26
  7  \w    106.00 167.00   1.00    1.00    --  106.22  77.00 -60.00   61
  8  \w     58.00  84.00   1.00    1.00    --   41.14-125.00 -90.00   26
  9  \w     39.00  67.00   1.00    1.00    --   41.14-125.00   0.00   28
 10  \w    125.00 177.00   1.00    1.00    --  106.22  15.00 150.00   52
 11  \w     31.00  56.00   1.00    1.00    --  106.22 -30.00 150.00   25
 12  \w    104.00 130.00   1.00    1.00    --  106.22 -30.00 150.00   26
 13  \w     56.00 105.00   1.00    1.00    --  106.22  15.00 150.00   49
 14  \w     37.00  63.00   1.00    1.00    --  106.22 -45.00 -30.00   26
 15  \w    -38.00 -13.00   1.00    1.00    --  -41.14 -57.00 120.00   25
 16  \w   -113.00 -53.00   1.00    1.00    --  -41.14 -57.00 120.00   60
 17  \w   -112.00 -72.00   1.00    1.00    --  -41.14 -38.00-120.00   40
 18  \w    -47.00 -11.00   1.00    1.00    --  -41.14 -77.00 120.00   36
 19  \w    -67.00 -18.00   1.00    1.00    --  -41.14 -38.00-120.00   49
 20  \w    -54.00 -11.00   1.00    1.00    --  -41.14 -77.00 -60.00   43
 21  \w    -84.00  -9.00   1.00    1.00    --  -41.14 -77.00-150.00   75
 22  \w    -98.00 -15.00   1.00    1.00    --  -41.14 -77.00  30.00   83
 23  \w    -65.00  33.00   1.00    1.00    --  -41.14  38.00-180.00   98
 24  \w    -52.00 -13.00   1.00    1.00    --  -41.14 -57.00  30.00   39
 25  \w     34.00  75.00   1.00    1.00    --   41.14 -99.00  30.00   41
 26  \w      2.00  28.00   1.00    1.00    --   41.14 -99.00  30.00   26
 27  \w     77.00 103.00   1.00    1.00    --  106.22  61.00 -30.00   26
 28  \w     77.00 103.00   1.00    1.00    --  106.22  61.00  90.00   26
 29  \w     79.00 114.00   1.00    1.00    --  106.22  61.00 -60.00   35
 30  \w     77.00 154.00   1.00    1.00    --  106.22  61.00 -90.00   77
 31  \w     77.00 104.00   1.00    1.00    --  106.22  61.00  30.00   27
 32  \w    138.00 164.00   1.00    1.00    --  106.22  77.00 120.00   26
 33  \w     27.00 104.00   1.00    1.00    --  106.22 -94.00 120.00   77
 34  \w     77.00 142.00   1.00    1.00    --  106.22  61.00-120.00   65
 35  \w     74.00 100.00   1.00    1.00    --  106.22  77.00 150.00   26
 36  \w     77.00 102.00   1.00    1.00    --  106.22  61.00  60.00   25
 37  \w     77.00 107.00   1.00    1.00    --  106.22  61.00 120.00   30
 38  \w     74.00 100.00   1.00    1.00    --  106.22  77.00  30.00   26
 39  \w     75.00 178.00   1.00    1.00    --  106.22  77.00   0.00  103
 40  \w     74.00  99.00   1.00    1.00    --  106.22  77.00-180.00   25
 41  \w     74.00 100.00   1.00    1.00    --  106.22  77.00 -60.00   26
 42  \w    151.00 177.00   1.00    1.00    --  106.22  77.00 -60.00   26
 43  \w     74.00 138.00   1.00    1.00    --  106.22  77.00-120.00   64
 44  \w     75.00 100.00   1.00    1.00    --  106.22  77.00 -90.00   25
 45  \w     81.00 107.00   1.00    1.00    --  106.22  45.00   0.00   26
 46  \w     63.00 117.00   1.00    1.00    --  106.22-125.00  90.00   54
 47  \w     74.00 124.00   1.00    1.00    --  106.22  77.00 120.00   50
 48  \w     74.00 100.00   1.00    1.00    --  106.22  77.00-150.00   26
 49  \w    152.00 177.00   1.00    1.00    --  106.22  73.00  54.00   25
 50  \w     81.00 107.00   1.00    1.00    --  106.22  61.00 150.00   26
 51  \w     78.00 104.00   1.00    1.00    --  106.22  61.00-180.00   26
 52  \w     75.00 100.00   1.00    1.00    --  106.22  73.00  54.00   25
 53  \w     47.00 103.00   1.00    1.00    --  106.22 -94.00-150.00   56
 54  \w     58.00 139.00   1.00    1.00    --  106.22 -77.00-120.00   81
 55  \w    117.00 172.00   1.00    1.00    --  106.22  77.00  90.00   55
 56  \w     75.00 101.00   1.00    1.00    --  106.22  77.00  90.00   26
 57  \w    143.00 178.00   1.00    1.00    --  106.22  77.00 -90.00   35
 58  \w     77.00 102.00   1.00    1.00    --  106.22  61.00-150.00   25
 59  \w    153.00 178.00   1.00    1.00    --  106.22  61.00 -60.00   25
 60  \w     77.00 106.00   1.00    1.00    --  106.22  61.00   0.00   29
;
_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      0.0124908000
_diffrn_orient_matrix_UB_12      0.0459118000
_diffrn_orient_matrix_UB_13      0.1245467000
_diffrn_orient_matrix_UB_21      -0.0844466000
_diffrn_orient_matrix_UB_22      -0.0080171000
_diffrn_orient_matrix_UB_23      0.0840925000
_diffrn_orient_matrix_UB_31      0.0370849000
_diffrn_orient_matrix_UB_32      -0.0337219000
_diffrn_orient_matrix_UB_33      0.1496269000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0482
_diffrn_reflns_av_unetI/netI     0.0197
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            25032
_diffrn_reflns_theta_full        73.37
_diffrn_reflns_theta_max         73.37
_diffrn_reflns_theta_min         5.35
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.696
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56683
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.086
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3223
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0384
_refine_ls_R_factor_gt           0.0382
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0643P)^2^+0.6991P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0922
_refine_ls_wR_factor_ref         0.0927
_reflns_number_gt                3186
_reflns_number_total             3223
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo9b02514_si_001.cif
_cod_data_source_block           19031105
_cod_original_cell_volume        3220.16(4)
_cod_database_code               4036059
_chemical_oxdiff_formula         CNOH
_chemical_oxdiff_usercomment     ZM-12-19-007
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C11(H8), C6(H11), C2(H12), C15(H14), C13(H17), C4(H18), C1(H19),
 C14(H20), C3(H21)
2.b Idealised Me refined as rotating group:
 C18(H22A,H22B,H22C), C17(H23A,H23B,H23C), C16(H2A,H2B,H2C)
;
_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 1.627
_oxdiff_exptl_absorpt_empirical_full_min 0.748