Unified Approach to Isoindolinones and THIQs via Lewis Acid Catalyzed Domino Mukaiyama-Mannich Lactamization/Alkylations: Application in the Synthesis of (±)-Homolaudanosine.
Dhanasekaran, Sivasankaran; Kayet, Anirban; Suneja, Arun; Bisai, Vishnumaya; Singh, Vinod K.; Organic letters 17 (2015) 2780–2783; doi:10.1021/acs.orglett.5b01197

data_1519850
_publ_section_title
;
 Unified Approach to Isoindolinones and THIQs via Lewis Acid Catalyzed
 Domino Mukaiyama-Mannich Lactamization/Alkylations: Application in the
 Synthesis of (+-)-Homolaudanosine.
;
_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              2780
_journal_page_last               2783
_journal_paper_doi               10.1021/acs.orglett.5b01197
_journal_volume                  17
_journal_year                    2015
_chemical_formula_sum            'C22 H16 Br N O2'
_chemical_formula_weight         406.27
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 96.930(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.7399(11)
_cell_length_b                   15.532(3)
_cell_length_c                   20.365(4)
_cell_measurement_reflns_used    4836
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.68
_cell_measurement_theta_min      2.40
_cell_volume                     1802.3(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0601
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_number            4639
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.697
_diffrn_reflns_theta_min         1.653
_diffrn_source                   Mo
_exptl_absorpt_coefficient_mu    2.297
_exptl_absorpt_correction_T_max  0.807
_exptl_absorpt_correction_T_min  0.624
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            WHITE
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_description       CHAR
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.638
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.991
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         4639
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.991
_refine_ls_R_factor_all          0.0939
_refine_ls_R_factor_gt           0.0487
_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^)+(0.0798P)^2^+0.2733P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1384
_refine_ls_wR_factor_ref         0.1582
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2667
_reflns_number_total             4639
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b01197_si_002.cif
_cod_data_source_block           shelx
_cod_depositor_comments          'Adding full bibliography for 1519850.cif.'
_cod_database_code               1519850
_shelx_estimated_absorpt_t_min   0.609
_shelx_estimated_absorpt_t_max   0.820
_shelxl_version_number           2014-3
_shelx_res_checksum              52197
_shelx_hkl_checksum              90315