New One-Pot Synthesis of 1,3,5-Triazines: Three-Component Condensation, Dimroth Rearrangement, and Dehydrogenative Aromatization.
Junaid, Ahmad; Lim, Felicia Phei Lin; Tiekink, Edward R. T.; Dolzhenko, Anton V.; ACS combinatorial science 21 (2019) 548–555; doi:10.1021/acscombsci.9b00079

data_4514918
_publ_section_title
;
 New One-Pot Synthesis of 1,3,5-Triazines: Three-Component Condensation,
 Dimroth Rearrangement, and Dehydrogenative Aromatization.
;
_journal_issue                   7
_journal_name_full               'ACS combinatorial science'
_journal_page_first              548
_journal_page_last               555
_journal_paper_doi               10.1021/acscombsci.9b00079
_journal_volume                  21
_journal_year                    2019
_chemical_formula_moiety         'C20 H23 N5 O'
_chemical_formula_sum            'C20 H23 N5 O'
_chemical_formula_weight         349.43
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 98.3940(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.31590(10)
_cell_length_b                   10.60040(10)
_cell_length_c                   12.13340(10)
_cell_measurement_reflns_used    47022
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.4410
_cell_measurement_theta_min      5.1760
_cell_volume                     1821.57(3)
_computing_cell_refinement
;
CrysAlisPro (Rigaku Oxford Diffraction, 2017)
;
_computing_data_collection
;
CrysAlisPro (Rigaku Oxford Diffraction, 2017)
;
_computing_data_reduction
;
CrysAlisPro (Rigaku Oxford Diffraction, 2017)
;
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 5.2558
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_av_unetI/netI     0.0089
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            84104
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.076
_diffrn_reflns_theta_max         67.076
_diffrn_reflns_theta_min         3.120
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.655
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.722
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'CrysAlisPro (Rigaku Oxford Diffraction, 2017)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_description       prism
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.145
_exptl_crystal_size_mid          0.122
_exptl_crystal_size_min          0.085
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3261
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0343
_refine_ls_R_factor_gt           0.0327
_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^)+(0.0468P)^2^+0.6415P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0851
_refine_ls_wR_factor_ref         0.0868
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3093
_reflns_number_total             3261
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            co9b00079_si_002.cif
_cod_data_source_block           shelx
_cod_database_code               4514918
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.911
_shelx_estimated_absorpt_t_max   0.946
_shelx_res_checksum              69071
_shelx_hkl_checksum              74935