Brønsted Acid Catalyzed Enantioselective α-Amidoalkylation in the Synthesis of Isoindoloisoquinolines
Eider Aranzamendi; Nuria Sotomayor; Esther Lete; Journal of Organic Chemistry 77 (2012) 2986–2991; doi:10.1021/jo3000223

data_4027077
_publ_section_title
;
 Br\/onsted Acid Catalyzed Enantioselective \a-Amidoalkylation in the
 Synthesis of Isoindoloisoquinolines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2986
_journal_page_last               2991
_journal_paper_doi               10.1021/jo3000223
_journal_volume                  77
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C26 H21 Br N2 O3, C H2 Cl2'
_chemical_formula_sum            'C27 H23 Br Cl2 N2 O3'
_chemical_formula_weight         574.28
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2011-10-20T13:43:45-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.72830(10)
_cell_length_b                   12.0028(2)
_cell_length_c                   23.2475(4)
_cell_measurement_reflns_used    7672
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.1911
_cell_measurement_theta_min      3.6795
_cell_measurement_wavelength     1.54184
_cell_volume                     2435.50(6)
_computing_cell_refinement       'CrysAlis Pro (Oxford Diffraction Ltd., 2011)'
_computing_data_collection       'CrysAlis Pro (Oxford Diffraction Ltd., 2011)'
_computing_data_reduction        'CrysAlis Pro (Oxford Diffraction Ltd., 2011)'
_computing_molecular_graphics    'Diamond v.3.2f (Crystal Impact GbR, 2008)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare et al, 1993)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4023
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details
;
  1 omega  -66.00   29.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.7631   38.0000   30.0000 95

  2 omega   12.00   98.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       40.7631 -125.0000  -60.0000 86

  3 omega   61.00  101.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       40.7631  150.0000  151.0000 40

  4 omega   44.00   71.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000 -180.0000 27

  5 omega   45.00   76.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  150.0000 31

  6 omega  114.00  157.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   60.0000 43

  7 omega   39.00   76.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  120.0000 37

  8 omega   39.00   71.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000   30.0000 32

  9 omega   42.00   76.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000    0.0000 34

 10 omega   85.00  157.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  111.0000  150.0000 72

 11 omega   44.00   70.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  -60.0000 26

 12 omega   58.00  138.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -15.0000    0.0000 80

 13 omega   65.00  147.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000    0.0000   60.0000 82

 14 omega  -70.00  -43.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.7631   77.0000   90.0000 27

 15 omega  -68.00   -4.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.7631  125.0000  120.0000 64

 16 omega    0.00   34.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.7631   77.0000   90.0000 34

 17 omega -116.00  -14.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.7631  -38.0000   30.0000 102

 18 omega   48.00   77.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000 -120.0000 29

 19 omega   38.00   76.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000 -150.0000 38

 20 omega   46.00  135.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -149.0000   28.0000 89

 21 omega   49.00  112.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -118.0000   37.0000 63

 22 omega   36.00  140.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000  120.0000 104

 23 omega   34.00   61.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -15.0000    0.0000 27

 24 omega   57.00  111.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -100.0000   78.0000 54

;
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Agilent SuperNova'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0907495
_diffrn_orient_matrix_UB_12      0.0754158
_diffrn_orient_matrix_UB_13      -0.0413529
_diffrn_orient_matrix_UB_21      0.0878923
_diffrn_orient_matrix_UB_22      0.0497904
_diffrn_orient_matrix_UB_23      0.0514188
_diffrn_orient_matrix_UB_31      0.1233476
_diffrn_orient_matrix_UB_32      -0.0910772
_diffrn_orient_matrix_UB_33      -0.0061309
_diffrn_radiation_monochromator  'Multilayer optics'
_diffrn_radiation_source         'Nova (Cu) x-ray micro-source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            18297
_diffrn_reflns_theta_full        76.39
_diffrn_reflns_theta_max         76.39
_diffrn_reflns_theta_min         3.8
_diffrn_source_current           0.8
_diffrn_source_power             0.04
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    4.595
_exptl_absorpt_correction_T_max  0.826
_exptl_absorpt_correction_T_min  0.554
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
        (compiled May 16 2011,17:55:39)
Analytical numeric absorption correction using a multifaceted crystal
                        model based on expressions derived by R.C. Clark & J.S.
        (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.566
_exptl_crystal_description       Fragment
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.2174
_exptl_crystal_size_mid          0.1577
_exptl_crystal_size_min          0.0573
_refine_diff_density_max         0.639
_refine_diff_density_min         -1.094
_refine_diff_density_rms         0.072
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.011(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     321
_refine_ls_number_reflns         5030
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.037
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0525P)^2^+2.0242P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0933
_refine_ls_wR_factor_ref         0.0963
_reflns_number_gt                4719
_reflns_number_total             5030
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            jo3000223_si_002.cif
_cod_data_source_block           ea251
_cod_database_code               4027077