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_4027710
_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_absolute_configuration rmad
_chemical_formula_moiety         'C50 H51 I N2 O16, 0.5(C5 H12)'
_chemical_formula_sum            'C52.5 H57 I N2 O16'
_chemical_formula_weight         1098.90
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_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_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                   19.5005(9)
_cell_length_b                   21.6527(10)
_cell_length_c                   24.7377(11)
_cell_measurement_reflns_used    9863
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      22.03
_cell_measurement_theta_min      2.2
_cell_volume                     10445.2(8)
_computing_cell_refinement       'SAINT (Bruker, 2006)'
_computing_data_collection       'SAINT (Bruker, 2006)'
_computing_data_reduction        'SAINT (Bruker, 2006)'
_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      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'SMART APEX2'
_diffrn_measurement_method       'CCD scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1382
_diffrn_reflns_av_sigmaI/netI    0.1132
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            147820
_diffrn_reflns_theta_full        27.86
_diffrn_reflns_theta_max         27.86
_diffrn_reflns_theta_min         1.33
_diffrn_source                   'sealed Tube'
_exptl_absorpt_coefficient_mu    0.684
_exptl_absorpt_correction_T_max  0.96484
_exptl_absorpt_correction_T_min  0.74376
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   Platon
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_description       plate
_exptl_crystal_F_000             4536
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.04
_refine_diff_density_max         2.010
_refine_diff_density_min         -0.771
_refine_diff_density_rms         0.080
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.028(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.861
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1338
_refine_ls_number_reflns         24850
_refine_ls_number_restraints     40
_refine_ls_restrained_S_all      0.866
_refine_ls_R_factor_all          0.1005
_refine_ls_R_factor_gt           0.0488
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0356P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.0850
_refine_ls_wR_factor_ref         0.0974
_reflns_number_gt                14486
_reflns_number_total             24850
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            jo3017378_si_002.cif
_cod_data_source_block           cs357
_cod_depositor_comments
;

2025-10-08
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C105 H114 I2 N4 O32'
_cod_original_formula_weight         2197.80
_cod_original_formula_moiety         '2(C50 H51 I N2 O16), C5 H12'
_cod_original_formula_units_Z            4
_cod_database_code               4027710