Substituent electronic effects govern direct intramolecular C-N cyclization of N-(Biphenyl)pyridin-2-amines induced by hypervalent iodine(III) reagents.
Chu, Jean-Ho; Hsu, Wen-Ting; Wu, Yi-Hua; Chiang, Meng-Fan; Hsu, Nan-Hai; Huang, Hao-Ping; Wu, Ming-Jung; The Journal of organic chemistry 79 (2014) 11395–11408; doi:10.1021/jo501822m

data_4030201
_publ_section_title
;
 Substituent electronic effects govern direct intramolecular C-N
 cyclization of N-(Biphenyl)pyridin-2-amines induced by hypervalent
 iodine(III) reagents.
;
_journal_issue                   23
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11395
_journal_page_last               11408
_journal_paper_doi               10.1021/jo501822m
_journal_volume                  79
_journal_year                    2014
_chemical_formula_moiety         'C17 H11 Cl N2'
_chemical_formula_sum            'C17 H11 Cl N2'
_chemical_formula_weight         278.73
_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
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_atom_sites_solution_secondary   difmap
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_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   3.8405(2)
_cell_length_b                   16.0573(9)
_cell_length_c                   25.5787(12)
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_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     1577.39(14)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_av_sigmaI/netI    0.0420
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -17
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_diffrn_reflns_limit_l_min       -29
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_diffrn_reflns_theta_max         25.01
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_exptl_absorpt_coefficient_mu    0.233
_exptl_absorpt_correction_T_max  0.9726
_exptl_absorpt_correction_T_min  0.9548
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.174
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.12
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_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.05(8)
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_refine_ls_number_reflns         2744
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_refine_ls_R_factor_all          0.0473
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_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0717P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1086
_refine_ls_wR_factor_ref         0.1118
_reflns_number_gt                2364
_reflns_number_total             2744
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo501822m_si_002.cif
_cod_data_source_block           a14003
_cod_depositor_comments
'Adding full bibliography for 4030200--4030201.cif.'
_cod_database_code               4030201