Organocatalytic Synthesis of 4-Aryl-1,2,3,4-tetrahydropyridines from Morita-Baylis-Hillman Carbonates through a One-Pot Three-Component Cyclization.
Wei, Jian; Li, Yuntong; Tao, Cheng; Wang, Huifei; Cheng, Bin; Zhai, Hongbin; Li, Yun; The Journal of organic chemistry 83 (2018) 835–842; doi:10.1021/acs.joc.7b02818

data_4033340
_publ_section_title
;
 Organocatalytic Synthesis of 4-Aryl-1,2,3,4-tetrahydropyridines from
 Morita-Baylis-Hillman Carbonates through a One-Pot Three-Component
 Cyclization.
;
_journal_issue                   2
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              835
_journal_page_last               842
_journal_paper_doi               10.1021/acs.joc.7b02818
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C22 H25 N O4'
_chemical_formula_sum            'C22 H25 N O4'
_chemical_formula_weight         367.43
_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   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-09-18
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Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
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_cell_angle_alpha                90
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_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.5277(6)
_cell_length_b                   28.377(2)
_cell_length_c                   8.7497(6)
_cell_measurement_reflns_used    1734
_cell_measurement_temperature    294.89(10)
_cell_measurement_theta_max      25.7780
_cell_measurement_theta_min      3.8250
_cell_volume                     2002.8(3)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      294.89(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega   -8.00   22.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5055  -99.0000   90.0000 30

  2 omega   35.00   85.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  178.0000  -30.0000 50

  3 omega   68.00  102.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  178.0000   90.0000 34

  4 omega  -18.00   17.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -57.0000  -90.0000 35

  5 omega  -48.00   46.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -57.0000  150.0000 94
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_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0549029000
_diffrn_orient_matrix_UB_12      -0.0194275000
_diffrn_orient_matrix_UB_13      0.0112759000
_diffrn_orient_matrix_UB_21      -0.0684695000
_diffrn_orient_matrix_UB_22      -0.0153315000
_diffrn_orient_matrix_UB_23      -0.0325149000
_diffrn_orient_matrix_UB_31      0.0050194000
_diffrn_orient_matrix_UB_32      0.0035462000
_diffrn_orient_matrix_UB_33      -0.0785240000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_unetI/netI     0.0434
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            8020
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.021
_diffrn_reflns_theta_min         3.612
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80768
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear dark red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.219
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
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_refine_ls_number_parameters     249
_refine_ls_number_reflns         3931
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_refine_ls_R_factor_all          0.0891
_refine_ls_R_factor_gt           0.0588
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_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0558P)^2^+0.4871P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
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_reflns_number_gt                2623
_reflns_number_total             3931
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b02818_si_003.cif
_cod_data_source_block           weijian_0411
_cod_depositor_comments
'Adding full bibliography for 4033337--4033340.cif.'
_cod_original_cell_volume        2002.8(2)
_cod_database_code               4033340
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C H N O'
_reflns_odcompleteness_completeness 99.60
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11), C15(H15), C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C4(H4), C6(H6), C7(H7), C8(H8), C9(H9)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C22(H22A,H22B,
 H22C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_res_checksum              77032
_shelx_hkl_checksum              44909
_olex2_date_sample_data_collection 2017-04-12
_olex2_submission_special_instructions 'No special instructions were received'