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_4033338
_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         'C18 H22 Br N O4'
_chemical_formula_sum            'C18 H22 Br N O4'
_chemical_formula_weight         396.27
_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
_audit_creation_method
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Olex2 1.2
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_cell_measurement_reflns_used    1741
_cell_measurement_temperature    289.48(10)
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_cell_measurement_theta_min      3.7910
_cell_volume                     3740.8(13)
_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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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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_diffrn_ambient_temperature      289.48(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
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  1 omega   -1.00   84.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6305   57.0000 -150.0000 85

  2 omega  -20.00   15.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6305  -99.0000   30.0000 35

  3 omega   57.50   92.50   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6305   77.0000  -60.0000 35

  4 omega  -50.00   45.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6305  -77.0000   90.0000 95
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_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
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_diffrn_orient_matrix_UB_13      -0.0166828000
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_diffrn_orient_matrix_UB_22      -0.0026717000
_diffrn_orient_matrix_UB_23      -0.0038191000
_diffrn_orient_matrix_UB_31      -0.0067957000
_diffrn_orient_matrix_UB_32      -0.0776064000
_diffrn_orient_matrix_UB_33      -0.0037165000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1032
_diffrn_reflns_av_unetI/netI     0.1788
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
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_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_limit_l_min       -50
_diffrn_reflns_number            15107
_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         26.020
_diffrn_reflns_theta_min         3.442
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.218
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.30156
_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 light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_description       block
_exptl_crystal_F_000             1632
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
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_refine_ls_extinction_method     none
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_refine_ls_number_reflns         7332
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_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
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'w=1/[\s^2^(Fo^2^)+(0.0336P)^2^] where P=(Fo^2^+2Fc^2^)/3'
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_reflns_number_gt                2734
_reflns_number_total             7332
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b02818_si_005.cif
_cod_data_source_block           weij_4_br
_cod_depositor_comments
'Adding full bibliography for 4033337--4033340.cif.'
_cod_original_cell_volume        3740.7(13)
_cod_database_code               4033338
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C H O N'
_reflns_odcompleteness_completeness 99.58
_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:
 C3(H3), C4(H4), C13(H13), C21(H21), C22(H22), C31(H31)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C36(H36A,H36B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C10(H10), C11(H11), C25(H25), C26(H26), C28(H28), C29(H29)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C17(H17A,H17B,H17C), C18(H18A,H18B,
 H18C), C32(H32A,H32B,H32C), C33(H33A,H33B,H33C), C35(H35A,H35B,H35C), C37(H37A,
 H37B,H37C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2), O6(H6)
;
_shelx_res_checksum              98894
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_olex2_date_sample_data_collection 2017-05-17
_olex2_submission_special_instructions 'No special instructions were received'