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_4033339
_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)
;
_cell_angle_alpha                90
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_cell_length_a                   16.8558(11)
_cell_length_b                   8.0593(5)
_cell_length_c                   29.356(2)
_cell_measurement_reflns_used    2797
_cell_measurement_temperature    289.23(13)
_cell_measurement_theta_max      22.9450
_cell_measurement_theta_min      3.4930
_cell_volume                     3843.3(5)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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)
;
_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)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
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_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      289.23(13)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_details
;
  1 omega -100.00  -71.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.3492  178.0000    0.0000 29

  2 omega  -11.00   23.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.3492  -99.0000  -30.0000 34

  3 omega  -44.00   78.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -19.0000 -120.0000 122

  4 omega   44.00  102.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  178.0000  -60.0000 58

  5 omega   -9.00   16.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   38.0000   60.0000 25

  6 omega   -9.00   96.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   38.0000  -60.0000 105
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
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_diffrn_orient_matrix_UB_11      0.0176954000
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_diffrn_orient_matrix_UB_33      -0.0197782000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
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_diffrn_reflns_av_unetI/netI     0.0740
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            22831
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         26.022
_diffrn_reflns_theta_min         3.317
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73568
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
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    1.270
_exptl_crystal_description       block
_exptl_crystal_F_000             1568
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.214
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_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
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_refine_ls_number_parameters     495
_refine_ls_number_reflns         7375
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.1125
_refine_ls_R_factor_gt           0.0643
_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^)+(0.0358P)^2^+1.7808P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1273
_refine_ls_wR_factor_ref         0.1527
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4435
_reflns_number_total             7375
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b02818_si_002.cif
_cod_data_source_block           weijian_1124_3
_cod_depositor_comments
;
Adding full bibliography for 4033337--4033340.cif.

2020-08-05
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_cell_volume        3843.3(4)
_cod_original_formula_moiety     '2(C22 H25 N O4)'
_cod_original_formula_sum        'C44 H50 N2 O8'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     734.86
_cod_database_code               4033339
_shelx_shelxl_version_number     2016/6
_reflns_odcompleteness_completeness 97.06
_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
2.a Ternary CH refined with riding coordinates:
 C11(H11), C12(H12), C33(H33), C34(H34)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C17(H17A,H17B), C35(H35A,H35B), C41(H41A,H41B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C24(H24), C25(H25),
 C26(H26), C28(H28), C29(H29), C30(H30), C31(H31)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C22(H22A,H22B,
 H22C), C39(H39A,H39B,H39C), C42(H42A,H42B,H42C), C43(H43A,H43B,H43C), C44(H44A,
 H44B,H44C)
;
_shelx_res_checksum              47648
_shelx_hkl_checksum              93449
_olex2_date_sample_data_collection 2016-11-24
_olex2_submission_special_instructions 'No special instructions were received'