Preparation, X-ray Structure, and Reactivity of 2-Iodylpyridines: Recyclable Hypervalent Iodine(V) Reagents
Akira Yoshimura; Christopher T. Banek; Mekhman S. Yusubov; Victor N. Nemykin; Viktor V. Zhdankin; Journal of Organic Chemistry 76 (2011) 3812–3819; doi:10.1021/jo200163m

data_4026288
_publ_contact_author_address
; 
 Department of Chemistry, 
 University of Minnesota Duluth, 
 1039 University Drive
 Duluth, MN 55812, USA. 
;
_publ_contact_author_email       vnemykin@d.umn.edu
_publ_contact_author_fax         '+1 218 726 7394'
_publ_contact_author_name        'Victor Nemykin'
_publ_contact_author_phone       '+1 218 726 6729'
_publ_section_title
;
 Preparation, X-ray Structure, and Reactivity of 2-Iodylpyridines:
 Recyclable Hypervalent Iodine(V) Reagents
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3812
_journal_page_last               3819
_journal_paper_doi               10.1021/jo200163m
_journal_volume                  76
_journal_year                    2011
_chemical_formula_moiety         'C5 H6 I1 N1 O3'
_chemical_formula_sum            'C5 H6 I N O3'
_chemical_formula_weight         255.01
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             09-03-03
_audit_creation_method           CRYSTALS_ver_12.85
_cell_angle_alpha                90
_cell_angle_beta                 107.3260(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.2624(7)
_cell_length_b                   14.4474(16)
_cell_length_c                   8.0465(9)
_cell_measurement_reflns_used    100
_cell_measurement_temperature    173
_cell_measurement_theta_max      18
_cell_measurement_theta_min      15
_cell_volume                     694.98(13)
_computing_cell_refinement       SHELXTL
_computing_data_collection       SHELXTL
_computing_data_reduction        SHELXTL
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      173
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       CCD
_diffrn_measurement_device_type  'Bruker APEX'
_diffrn_measurement_method       \w/2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.000
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1659
_diffrn_reflns_theta_full        27.466
_diffrn_reflns_theta_max         27.466
_diffrn_reflns_theta_min         2.820
_diffrn_standards_decay_%        0.00
_diffrn_standards_interval_time  5
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    4.552
_exptl_absorpt_correction_T_max  0.63
_exptl_absorpt_correction_T_min  0.36
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.437
_exptl_crystal_description       block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.54
_refine_diff_density_min         -0.33
_refine_ls_extinction_coef       100(2)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   1.0552
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     92
_refine_ls_number_reflns         1451
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0168
_refine_ls_R_factor_gt           0.0148
_refine_ls_shift/su_max          0.002449
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.01P)^2^ + 0.96P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0344
_refine_ls_wR_factor_gt          0.0337
_refine_ls_wR_factor_ref         0.0329
_reflns_limit_h_max              7
_reflns_limit_h_min              -8
_reflns_limit_k_max              18
_reflns_limit_k_min              0
_reflns_limit_l_max              10
_reflns_limit_l_min              0
_reflns_number_gt                1486
_reflns_number_total             1587
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   0.70
_oxford_diffrn_Wilson_scale      3.63
_oxford_refine_ls_r_factor_ref   0.0138
_oxford_refine_ls_scale          0.5870(11)
_oxford_reflns_number_all        1581
_oxford_reflns_threshold_expression_ref I>3.0\s(I)
_oxford_structure_analysis_title '2-IO2Py -100oC in P2(1)/c'
_cod_data_source_file            jo200163m_si_001.cif
_cod_data_source_block           1
_cod_original_sg_symbol_Hall     '-P 2ybc '
_cod_original_sg_symbol_H-M      'P 1 21/c 1 '
_cod_original_formula_sum        'C5 H6 I1 N1 O3'
_cod_database_code               4026288