Regio- and Stereoselective Synthesis of Isoindolin-1-ones through BuLi-Mediated Iodoaminocyclization of 2-(1-Alkynyl)benzamides.
Brahmchari, Dhirendra; Verma, Akhilesh K.; Mehta, Saurabh; The Journal of organic chemistry 83 (2018) 3339–3347; doi:10.1021/acs.joc.7b02903

data_4035168
_publ_section_title
;
 Regio- and Stereoselective Synthesis of Isoindolin-1-ones through
 BuLi-Mediated Iodoaminocyclization of 2-(1-Alkynyl)benzamides.
;
_journal_issue                   6
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3339
_journal_page_last               3347
_journal_paper_doi               10.1021/acs.joc.7b02903
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C15 H10 I N O, 0.25C H3 O H, 0.5H2O'
_chemical_formula_sum            'C15.25 H10 I N O1.75'
_chemical_formula_weight         362.14
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90.852(2)
_cell_angle_beta                 104.066(2)
_cell_angle_gamma                103.825(2)
_cell_formula_units_Z            8
_cell_length_a                   13.8012(4)
_cell_length_b                   14.1127(5)
_cell_length_c                   15.8686(6)
_cell_measurement_reflns_used    9334
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      29.28
_cell_measurement_theta_min      2.30
_cell_volume                     2902.49(18)
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
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_computing_molecular_graphics
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
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_computing_structure_solution    'SIR92 (Altornare et al., 1993)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       '\w and \f scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
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_diffrn_reflns_av_R_equivalents  0.0463
_diffrn_reflns_av_unetI/netI     0.0380
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            61748
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.300
_exptl_absorpt_coefficient_mu    2.202
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.6350
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2004)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.657
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             1404
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.966
_refine_diff_density_min         -0.993
_refine_diff_density_rms         0.123
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     712
_refine_ls_number_reflns         10202
_refine_ls_number_restraints     98
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0838
_refine_ls_R_factor_gt           0.0501
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0681P)^2^+12.7593P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1282
_refine_ls_wR_factor_ref         0.1562
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6834
_reflns_number_total             10202
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b02903_si_002.cif
_cod_data_source_block           B37
_cod_database_code               4035168
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.667
_shelx_estimated_absorpt_t_max   0.810
_shelx_res_checksum              74825
_shelx_hkl_checksum              27053