Synthesis of highly functionalized 1,6-dihydropyridines via the Zn(OTf)<sub>2</sub>-catalyzed three-component cascade reaction of aldimines and two alkynes (IA<sup>2</sup>-coupling).
Shehzadi, Syeda Aaliya; Vande Velde, Christophe M. L.; Saeed, Aamer; Abbaspour Tehrani, Kourosch; Organic & biomolecular chemistry 16 (2018) 3241–3247; doi:10.1039/c8ob00195b

data_1549216
_publ_section_title
;
 Synthesis of highly functionalized 1,6-dihydropyridines via the
 Zn(OTf)<sub>2</sub>-catalyzed three-component cascade reaction of
 aldimines and two alkynes (IA<sup>2</sup>-coupling).
;
_journal_issue                   17
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3241
_journal_page_last               3247
_journal_paper_doi               10.1039/c8ob00195b
_journal_volume                  16
_journal_year                    2018
_chemical_formula_moiety         'C20 H27 N O2'
_chemical_formula_sum            'C20 H27 N O2'
_chemical_formula_weight         313.42
_chemical_name_systematic
;
methyl-2-(tert-butyl)-4-phenyl-1-propyl-1,2 dihydropyridine-3-carboxylate'
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/4
_audit_update_record
;
2018-01-05 deposited with the CCDC.
2018-04-04 downloaded from the CCDC.
;
_cell_angle_alpha                94.970(4)
_cell_angle_beta                 103.881(4)
_cell_angle_gamma                109.494(4)
_cell_formula_units_Z            4
_cell_length_a                   11.9792(6)
_cell_length_b                   12.1131(5)
_cell_length_c                   13.4962(7)
_cell_measurement_reflns_used    4837
_cell_measurement_temperature    99.96(10)
_cell_measurement_theta_max      74.8940
_cell_measurement_theta_min      3.9240
_cell_volume                     1762.21(16)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      99.96(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4839
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_av_unetI/netI     0.0295
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -12
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_diffrn_reflns_limit_k_min       -15
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_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12090
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.959
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_diffrn_reflns_theta_max         74.988
_diffrn_reflns_theta_min         3.431
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.589
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88646
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.181
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
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_refine_ls_number_reflns         6966
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0517
_refine_ls_R_factor_gt           0.0430
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0683P)^2^+0.2432P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1130
_refine_ls_wR_factor_ref         0.1220
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5825
_reflns_number_total             6966
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob00195b2.cif
_cod_data_source_block           sas5-109
_cod_depositor_comments
'Adding full bibliography for 1549215--1549216.cif.'
_cod_original_cell_volume        1762.22(16)
_cod_database_code               1549216
_shelx_shelxl_version_number     2016/4
_shelx_res_checksum              59156