Electrophilic ipso-iodocyclization of N-benzyl-N-(1-naphthyl)propiolamides: synthesis of complex polycyclic lactams.
Wang, Li-Jing; Zhu, Hai-Tao; Qiu, Yi-Feng; Liu, Xue-Yuan; Liang, Yong-Min; Organic & biomolecular chemistry 12 (2014) 643–650; doi:10.1039/c3ob42020e

data_7153573
_publ_section_title
;
 Electrophilic ipso-iodocyclization of
 N-benzyl-N-(1-naphthyl)propiolamides: synthesis of complex polycyclic
 lactams.
;
_journal_issue                   4
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              643
_journal_page_last               650
_journal_paper_doi               10.1039/c3ob42020e
_journal_volume                  12
_journal_year                    2014
_chemical_formula_moiety         'C26 H18 I N O'
_chemical_formula_sum            'C26 H18 I N O'
_chemical_formula_weight         487.31
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2012-10-29
_audit_creation_method
;
Olex2 1.2
(compiled 2012.05.09 svn.r2324, GUI svn.r4230)
;
_cell_angle_alpha                75.073(5)
_cell_angle_beta                 77.631(4)
_cell_angle_gamma                87.141(4)
_cell_formula_units_Z            4
_cell_length_a                   9.6284(4)
_cell_length_b                   11.7266(6)
_cell_length_c                   19.1651(9)
_cell_measurement_reflns_used    4658
_cell_measurement_temperature    293.83(10)
_cell_measurement_theta_max      28.4848
_cell_measurement_theta_min      3.0168
_cell_volume                     2042.31(17)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      293.83(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9175
_diffrn_measured_fraction_theta_max 0.9628
_diffrn_measurement_details
;
1 omega 12.00 50.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- -19.3492 57.0000 -150.0000 38

2 omega -13.00 14.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- -19.3492 -99.0000 -30.0000 27

3 omega 39.00 66.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- 22.6305 -99.0000 -180.0000 27

4 omega -1.00 42.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- 22.6305 57.0000 -60.0000 43

5 omega 36.00 61.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- 22.6305 178.0000 120.0000 25

6 omega 6.00 93.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- 22.6305 57.0000 -180.0000 87

7 omega -1.00 90.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- 22.6305 57.0000 90.0000 91

8 omega -48.00 -20.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- 22.6305 -57.0000 -60.0000 28
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0340843000
_diffrn_orient_matrix_UB_12      0.0258136000
_diffrn_orient_matrix_UB_13      -0.0370607000
_diffrn_orient_matrix_UB_21      -0.0216026000
_diffrn_orient_matrix_UB_22      -0.0485839000
_diffrn_orient_matrix_UB_23      -0.0108914000
_diffrn_orient_matrix_UB_31      -0.0637152000
_diffrn_orient_matrix_UB_32      0.0298660000
_diffrn_orient_matrix_UB_33      -0.0064604000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_av_unetI/netI     0.0464
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            12142
_diffrn_reflns_theta_full        25.68
_diffrn_reflns_theta_max         25.68
_diffrn_reflns_theta_min         3.02
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.585
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96879
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light orange'
_exptl_crystal_density_diffrn    1.585
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.617
_refine_diff_density_min         -0.803
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     523
_refine_ls_number_reflns         7160
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0393
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0227P)^2^+1.0796P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0713
_refine_ls_wR_factor_ref         0.0810
_reflns_number_gt                5491
_reflns_number_total             7160
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ob42020e.txt
_cod_data_source_block           exp_335
_cod_original_cell_volume        2042.32(17)
_cod_database_code               7153573
_reflns_odcompleteness_completeness 91.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32