Direct Synthesis of β-Aminoenals through Reaction of 1,2,3-Triazine with Secondary Amines.
Quiñones, Ryan E; Glinkerman, Christopher M.; Zhu, Kaicheng; Boger, Dale L.; Organic letters 19 (2017) 3568–3571; doi:10.1021/acs.orglett.7b01543

data_1546421
_publ_section_title
;
 Direct Synthesis of \b-Aminoenals through Reaction of 1,2,3-Triazine with
 Secondary Amines.
;
_journal_issue                   13
_journal_name_full               'Organic letters'
_journal_page_first              3568
_journal_page_last               3571
_journal_paper_doi               10.1021/acs.orglett.7b01543
_journal_volume                  19
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'H O4 S, C23 H22 N5 O4'
_chemical_formula_sum            'C23 H23 N5 O8 S'
_chemical_formula_weight         529.52
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2016-12-01
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2016.11.24 svn.r3356 for OlexSys, GUI svn.r5267)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   31.325(3)
_cell_length_b                   4.7080(4)
_cell_length_c                   15.8478(11)
_cell_measurement_reflns_used    5257
_cell_measurement_temperature    100
_cell_measurement_theta_max      68.260
_cell_measurement_theta_min      2.824
_cell_volume                     2337.2(3)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.963
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0554
_diffrn_reflns_av_unetI/netI     0.0590
_diffrn_reflns_Laue_measured_fraction_full 0.963
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11831
_diffrn_reflns_point_group_measured_fraction_full 0.802
_diffrn_reflns_point_group_measured_fraction_max 0.801
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.370
_diffrn_reflns_theta_min         2.821
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.771
_exptl_absorpt_correction_T_max  0.5210
_exptl_absorpt_correction_T_min  0.3779
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0994 before and 0.0779 after correction.
The Ratio of minimum to maximum transmission is 0.7253.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.505
_exptl_crystal_description       plate
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.738
_refine_diff_density_min         -0.513
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details
;
 Flack x determined using 906 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     364
_refine_ls_number_reflns         3440
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0614
_refine_ls_R_factor_gt           0.0524
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0766P)^2^+1.8797P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1341
_refine_ls_wR_factor_ref         0.1393
_reflns_Friedel_coverage         0.603
_reflns_Friedel_fraction_full    0.627
_reflns_Friedel_fraction_max     0.628
_reflns_number_gt                3029
_reflns_number_total             3440
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b01543_si_002.cif
_cod_data_source_block           boger55_a
_cod_depositor_comments          'Adding full bibliography for 1546421.cif.'
_cod_database_code               1546421
_shelx_estimated_absorpt_t_max   0.949
_shelx_estimated_absorpt_t_min   0.619
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2. Rigid body (RIGU) restrains
 O8, O6', O7, O8', O5, O5', O6
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
3. Others
 Sof(O5)=Sof(O6)=Sof(O7)=Sof(H7A)=1-FVAR(1)
 Sof(O5')=Sof(O6')=Sof(O8')=Sof(H8')=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C17(H17A,H17B)
4.b Aromatic/amide H refined with riding coordinates:
 N2(H2), N3(H3), C19(H19), C2(H2A), C9(H9), C14(H14), C15(H15), C4(H4),
 C16(H16), C13(H13), C12(H12), C8(H8), C7(H7), C5(H5), C20(H20), C23(H23),
 C22(H22), C21(H21)
4.c Idealised tetrahedral OH refined as rotating group:
 O8'(H8'), O7(H7A)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'