Control of the Dual Reactivity (Iminium-Dienamine) of β-Arylmethyl α,β-Unsaturated Aldehydes in Organocatalytic 1,3-Dipolar Cycloadditions with N-Benzoyl C,N-Cyclic Azomethine Imines.
Izquierdo, Cristina; Esteban, Francisco; Parra, Alejandro; Alfaro, Ricardo; Alemán, José; Fraile, Alberto; Ruano, José Luis García; The Journal of organic chemistry 79 (2014) 10417–; doi:10.1021/jo5018519

data_4030099
_publ_section_title
;
 Control of the Dual Reactivity (Iminium-Dienamine) of \b-Arylmethyl
 \a,\b-Unsaturated Aldehydes in Organocatalytic 1,3-Dipolar Cycloadditions
 with N-Benzoyl C,N-Cyclic Azomethine Imines.
;
_journal_issue                   21
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10417
_journal_paper_doi               10.1021/jo5018519
_journal_volume                  79
_journal_year                    2014
_chemical_formula_sum            'C33 H33 Br Cl N3 O'
_chemical_formula_weight         602.98
_chemical_name_common            JJ-ad
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 96.3060(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.9668(5)
_cell_length_b                   10.1098(4)
_cell_length_c                   22.2147(9)
_cell_measurement_reflns_used    5831
_cell_measurement_temperature    296.(2)
_cell_measurement_theta_max      19.7831
_cell_measurement_theta_min      2.4360
_cell_volume                     3341.0(2)
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_collection       'Bruker Instrument Service v2010.9.0.0'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0453
_diffrn_reflns_av_sigmaI/netI    0.0744
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            31648
_diffrn_reflns_theta_full        25.41
_diffrn_reflns_theta_max         25.41
_diffrn_reflns_theta_min         1.56
_exptl_absorpt_coefficient_mu    1.337
_exptl_absorpt_correction_T_max  0.92
_exptl_absorpt_correction_T_min  0.78
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.199
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.060
_refine_diff_density_max         1.241
_refine_diff_density_min         -0.469
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.012(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     703
_refine_ls_number_reflns         12101
_refine_ls_number_restraints     73
_refine_ls_restrained_S_all      0.994
_refine_ls_R_factor_all          0.1100
_refine_ls_R_factor_gt           0.0620
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1393P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1820
_refine_ls_wR_factor_ref         0.2145
_reflns_number_gt                7739
_reflns_number_total             12101
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5018519_si_003.cif
_cod_data_source_block           I
_cod_depositor_comments
'Adding full bibliography for 4030099--4030101.cif.'
_cod_database_code               4030099