Transition Metal-Free Superbase-Catalyzed C-H Vinylation of Aldimines with Acetylenes to 1-Azadienes.
Schmidt, Elena Yu; Bidusenko, Ivan A.; Protsuk, Nadezhda I.; Demyanov, Yan; Ushakov, Igor A.; Vashchenko, Alexander Valentine; Trofimov, Boris A.; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.9b03192

data_4037929
_publ_section_title
;
 Transition Metal-Free Superbase-Catalyzed C-H Vinylation of Aldimines
 with Acetylenes to 1-Azadienes.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b03192
_journal_year                    2020
_chemical_formula_moiety         'C21 H17 N'
_chemical_formula_sum            'C21 H17 N'
_chemical_formula_weight         283.36
_chemical_name_systematic        N,1,3-triphenylprop-2-en-1-imine
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-10-23
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-10-23 # Formatted by publCIF

;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.669(2)
_cell_length_b                   10.1689(13)
_cell_length_c                   18.228(2)
_cell_measurement_reflns_used    1375
_cell_measurement_temperature    297.15
_cell_measurement_theta_max      22.1
_cell_measurement_theta_min      2.4
_cell_volume                     3275.1(7)
_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      297.15
_diffrn_measured_fraction_theta_full 0.772
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\w and \f'
_diffrn_radiation_monochromator  No
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1494
_diffrn_reflns_av_unetI/netI     0.0563
_diffrn_reflns_Laue_measured_fraction_full 0.772
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            47622
_diffrn_reflns_point_group_measured_fraction_full 0.772
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.031
_diffrn_reflns_theta_min         2.235
_diffrn_source                   IuS
_exptl_absorpt_coefficient_mu    0.066
_exptl_absorpt_correction_T_max  0.7449
_exptl_absorpt_correction_T_min  0.6564
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1365 before and 0.0665 after correction. The Ratio of minimum to maximum transmission is 0.8812. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.149
_exptl_crystal_description       plate
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.301
_exptl_crystal_size_mid          0.115
_exptl_crystal_size_min          0.022
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.0073(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2284
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.1288
_refine_ls_R_factor_gt           0.0602
_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^)+(0.0643P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1205
_refine_ls_wR_factor_ref         0.1433
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1330
_reflns_number_total             2284
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b03192_si_002.cif
_cod_data_source_block           b
_cod_original_cell_volume        3275.2(7)
_cod_database_code               4037929
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.999
_shelx_estimated_absorpt_t_min   0.980
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C6(H6), C7(H7), C9(H9), C10(H10), C11(H11), C12(H12),
 C13(H13), C15(H15), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21)
;
_shelx_res_checksum              53180
_shelx_hkl_checksum              57227
_olex2_submission_special_instructions 'No special instructions were received'
_publcif_funding_html
;
;