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_7153574
_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         'C22 H16 I N O'
_chemical_formula_sum            'C22 H16 I N O'
_chemical_formula_weight         437.26
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_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     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-03-01
_audit_creation_method
;
Olex2 1.2
(compiled Dec 5 2012 16:20:19, GUI svn.r4385)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   10.5172(8)
_cell_length_b                   17.5717(6)
_cell_length_c                   20.0963(11)
_cell_measurement_reflns_used    2440
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.8110
_cell_measurement_theta_min      3.6260
_cell_volume                     3713.9(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec 3 2012,18:21:49)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec 3 2012,18:21:49)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec 3 2012,18:21:49)
;
_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    'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9970
_diffrn_measured_fraction_theta_max 0.9080
_diffrn_measurement_details
;
1 omega 8.00 77.00 1.5000 12.0000
omega____ theta____ kappa____ phi______ frames
- 22.6305 57.0000 -30.0000 46

2 omega -51.00 6.00 1.5000 12.0000
omega____ theta____ kappa____ phi______ frames
- 22.6305 -38.0000 0.0000 38

3 omega 10.00 41.50 1.5000 12.0000
omega____ theta____ kappa____ phi______ frames
- 22.6305 -99.0000 -30.0000 21

4 omega 38.00 98.00 1.5000 12.0000
omega____ theta____ kappa____ phi______ frames
- 22.6305 -178.0000 -90.0000 40
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0214669000
_diffrn_orient_matrix_UB_12      -0.0104219000
_diffrn_orient_matrix_UB_13      0.0321938000
_diffrn_orient_matrix_UB_21      -0.0090184000
_diffrn_orient_matrix_UB_22      0.0379438000
_diffrn_orient_matrix_UB_23      0.0110904000
_diffrn_orient_matrix_UB_31      -0.0632917000
_diffrn_orient_matrix_UB_32      -0.0089314000
_diffrn_orient_matrix_UB_33      0.0093158000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0519
_diffrn_reflns_av_unetI/netI     0.0624
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            13199
_diffrn_reflns_theta_full        28.55
_diffrn_reflns_theta_max         28.55
_diffrn_reflns_theta_min         3.03
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.733
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69184
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec 3 2012,18:21:49)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.564
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1728
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.25
_refine_diff_density_max         1.391
_refine_diff_density_min         -0.623
_refine_diff_density_rms         0.087
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         4308
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.106
_refine_ls_R_factor_all          0.1465
_refine_ls_R_factor_gt           0.0741
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0254P)^2^+14.9618P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1273
_refine_ls_wR_factor_ref         0.1546
_reflns_number_gt                2224
_reflns_number_total             4308
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ob42020e.txt
_cod_data_source_block           wanglj_0117
_cod_database_code               7153574
_reflns_odcompleteness_completeness 99.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
H22 of C22, H21 of C21, H20 of C20, H19 of C19, H18 of C18, H5 of C5, H6 of
C6, H7 of C7, H8 of C8, H11 of C11, H12 of C12, H13 of C13, H14 of C14, H15
of C15, {H16A,H16B} of C16
2.a Secondary CH2 refined with riding coordinates:
C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
C5(H5), C6(H6), C7(H7), C8(H8), C11(H11), C12(H12), C13(H13), C14(H14),
C15(H15), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22)
;