Synthesis of 3-substituted isoindolin-1-ones via a tandem desilylation, cross-coupling, hydroamidation sequence under aqueous phase-transfer conditions.
Munoz, Socrates B.; Aloia, Alexandra N.; Moore, Alexander K.; Papp, Attila; Mathew, Thomas; Fustero, Santos; Olah, George A.; Surya Prakash, G. K.; Organic & biomolecular chemistry 14 (2016) 85–92; doi:10.1039/c5ob02187a

data_7154808
_publ_section_title
;
 Synthesis of 3-substituted isoindolin-1-ones via a tandem desilylation,
 cross-coupling, hydroamidation sequence under aqueous phase-transfer
 conditions.
;
_journal_issue                   1
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              85
_journal_page_last               92
_journal_paper_doi               10.1039/c5ob02187a
_journal_volume                  14
_journal_year                    2016
_chemical_formula_moiety         'C13 H13 N O'
_chemical_formula_sum            'C13 H13 N O'
_chemical_formula_weight         199.24
_chemical_name_systematic
(Z)-3-(cyclopropylmethylene)-2-methylisoindolin-1-one
_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   geom
_audit_update_record
;
2015-09-24 deposited with the CCDC.
2015-11-20 downloaded from the CCDC.
;
_cell_angle_alpha                89.9200(19)
_cell_angle_beta                 88.182(2)
_cell_angle_gamma                88.4170(19)
_cell_formula_units_Z            4
_cell_length_a                   7.6694(8)
_cell_length_b                   8.4024(8)
_cell_length_c                   15.7611(16)
_cell_measurement_reflns_used    9991
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      30.6274
_cell_measurement_theta_min      2.4251
_cell_volume                     1014.77(18)
_computing_cell_refinement       'APEX2 v2014.1-1 (Bruker AXS)'
_computing_data_collection       'Bruker Instrument Service v2012.12.0.3'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS, 2013)'
_computing_structure_refinement  'SHELXTL XLMP 2014/1 (Bruker AXS)'
_computing_structure_solution    'SHELXTL XT 2014/1 (Bruker AXS)'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker APEX II CCD'
_diffrn_measurement_method       'omega- and phi-scans'
_diffrn_radiation_monochromator  'TRIUMPH curved-crystal'
_diffrn_radiation_type           'MoK\a '
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            21818
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         30.62
_diffrn_reflns_theta_min         1.29
_diffrn_source                   'fine-focus tube'
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.90
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS V2012/1'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.602
_exptl_crystal_size_mid          0.248
_exptl_crystal_size_min          0.240
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.256
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         6087
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0428
_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^)+(0.0537P)^2^+0.2789P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1032
_refine_ls_wR_factor_ref         0.1121
_reflns_number_gt                4887
_reflns_number_total             6087
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ob02187a2.cif
_cod_data_source_block           I
_cod_depositor_comments
'Adding full bibliography for 7154808--7154809.cif.'
_cod_database_code               7154808
_shelx_res_checksum              16380