Iodocyclization of o-Alkynylbenzamides Revisited: Formation of Isobenzofuran-1(3H)-imines and 1H-Isochromen-1-imines Instead of Lactams
Claudine Schlemmer; Lars Andernach; Dieter Schollmeyer; Bernd F. Straub; Till Opatz; Journal of Organic Chemistry 77 (2012) 10118–10124; doi:10.1021/jo3017378

data_4027714
_publ_section_title
;
 Iodocyclization of o-Alkynylbenzamides Revisited: Formation of
 Isobenzofuran-1(3H)-imines and 1H-Isochromen-1-imines Instead of Lactams
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              10118
_journal_page_last               10124
_journal_paper_doi               10.1021/jo3017378
_journal_volume                  77
_journal_year                    2012
_chemical_formula_moiety         'C21 H14 I N O'
_chemical_formula_sum            'C21 H14 I N O'
_chemical_formula_weight         423.23
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   17.3734(7)
_cell_length_b                   8.1254(4)
_cell_length_c                   23.7944(16)
_cell_measurement_reflns_used    5709
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      28.34
_cell_measurement_theta_min      2.90
_cell_volume                     3359.0(3)
_computing_cell_refinement       'STOE X-AREA'
_computing_data_collection       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR-97 (Altomare, 1999)'
_diffrn_ambient_temperature      193(2)
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_area_resol_mean 6.67
_diffrn_detector_type            STOE
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      ' 180 frames, detector distance = 80 mm'
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0860
_diffrn_reflns_av_sigmaI/netI    0.0458
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            26762
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         2.90
_diffrn_source                   'sealed Tube'
_exptl_absorpt_coefficient_mu    1.913
_exptl_absorpt_correction_T_max  0.9392
_exptl_absorpt_correction_T_min  0.4305
_exptl_absorpt_correction_type   integration
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.674
_exptl_crystal_description       needle
_exptl_crystal_F_000             1664
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.973
_refine_diff_density_min         -1.292
_refine_diff_density_rms         0.108
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.917
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         4062
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.917
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0333
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0474P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.0773
_refine_ls_wR_factor_ref         0.0838
_reflns_number_gt                2802
_reflns_number_total             4062
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            jo3017378_si_006.cif
_cod_data_source_block           cs387a
_cod_database_code               4027714