Synthesis of 1,6-Dihydropyridine-3-carbonitrile Derivatives via Lewis Acid-Catalyzed Annulation of Propargylic Alcohols with (E)-3-amino-3-phenylacrylonitriles.
Du, Li-Juan; Zhang, Yuecheng; Zhang, Hong-Yu; Yin, Guohui; Wang, Xiao-Yan; Zhao, Jiquan; Han, Ya-Ping; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c01171

data_4038606
_publ_section_title
;
 Synthesis of 1,6-Dihydropyridine-3-carbonitrile Derivatives via Lewis
 Acid-Catalyzed Annulation of Propargylic Alcohols with
 (E)-3-amino-3-phenylacrylonitriles.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c01171
_journal_year                    2020
_chemical_formula_moiety         'C32 H26 N2 O'
_chemical_formula_sum            'C32 H24 N2 O'
_chemical_formula_weight         452.53
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
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Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
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_cell_length_c                   14.7380(7)
_cell_measurement_reflns_used    1775
_cell_measurement_temperature    292.90(10)
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_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
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_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
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_diffrn_measurement_details
;
  1 omega   -8.00   32.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -57.0000   30.0000 40

  2 omega   16.00   46.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.4273  -19.0000  120.0000 30

  3 omega   34.00   86.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867 -178.0000   60.0000 52

  4 omega  -47.00   46.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -57.0000 -180.0000 93

  5 omega  -76.00  -42.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.4273  -19.0000  120.0000 34
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_diffrn_orient_matrix_UB_22      -0.0094300000
_diffrn_orient_matrix_UB_23      0.0382271000
_diffrn_orient_matrix_UB_31      0.0317651000
_diffrn_orient_matrix_UB_32      -0.0208676000
_diffrn_orient_matrix_UB_33      -0.0301780000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_unetI/netI     0.0533
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
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_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10125
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.022
_diffrn_reflns_theta_min         3.518
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.072
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_exptl_absorpt_correction_T_min  0.80414
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
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_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
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_exptl_crystal_density_diffrn    1.196
_exptl_crystal_description       block
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.508
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_refine_diff_density_rms         0.044
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_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
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'w=1/[\s^2^(Fo^2^)+(0.0569P)^2^+2.7365P] where P=(Fo^2^+2Fc^2^)/3'
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_refine_ls_wR_factor_ref         0.2198
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_reflns_number_gt                2912
_reflns_number_total             4934
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_cod_database_code               4038606
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_reflns_odcompleteness_iscentric 1
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_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C6(H6), C13(H13), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20), C21(H21), C22(H22), C23(H23), C26(H26), C27(H27), C28(H28),
  C29(H29), C30(H30), C31(H31), C0AA(H0AA)
2.b Idealised Me refined as rotating group:
 C33(H33A,H33B,H33C), C1AA(H1AA,H1AB,H1AC)
;
_shelx_res_checksum              76401
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_olex2_date_sample_data_collection 2019-04-24
_olex2_submission_special_instructions 'No special instructions were received'