Internal delivery of soft chlorine and bromine atoms: stereoselective synthesis of (E)-beta-halogenovinyl(aryl)-lambda3-iodanes through domino lambda3-iodanation-1,4-halogen shift-fluorination of alkynes.
Ochiai, Masahito; Hirobe, Masaya; Yoshimura, Akira; Nishi, Yoshio; Miyamoto, Kazunori; Shiro, Motoo; Organic letters 9 (2007) 3335–3338; doi:10.1021/ol071345q

data_1505493
_publ_section_title
;
 Internal delivery of soft chlorine and bromine atoms: stereoselective
 synthesis of (E)-beta-halogenovinyl(aryl)-lambda3-iodanes through domino
 lambda3-iodanation-1,4-halogen shift-fluorination of alkynes.
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              3335
_journal_page_last               3338
_journal_paper_doi               10.1021/ol071345q
_journal_volume                  9
_journal_year                    2007
_chemical_formula_moiety         'C13 H16 Cl F I, B F4 '
_chemical_formula_sum            'C13 H16 B Cl F5 I'
_chemical_formula_weight         440.43
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_cell_angle_alpha                90.0000
_cell_angle_beta                 100.597(5)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   6.3772(18)
_cell_length_b                   17.736(5)
_cell_length_c                   14.396(4)
_cell_measurement_reflns_used    4425
_cell_measurement_temperature    100.1
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.1
_cell_volume                     1600.5(8)
_computing_cell_refinement       'CrystalClear (R/MSC, 2005)'
_computing_data_collection       'CrystalClear (R/MSC, 2005)'
_computing_data_reduction        'CrystalStructure (R/MSC, Rigaku, 2005)'
_computing_molecular_graphics    'ORTEP (Johnson, 1976)'
_computing_publication_material  'CrystalStructure (R/MSC, Rigaku, 2005)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.037
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12701
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.47
_exptl_absorpt_coefficient_mu    2.208
_exptl_absorpt_correction_T_max  0.876
_exptl_absorpt_correction_T_min  0.754
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.828
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             856.00
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_refine_diff_density_max         2.73
_refine_diff_density_min         -0.84
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     193
_refine_ls_number_reflns         3566
_refine_ls_R_factor_gt           0.0356
_refine_ls_shift/su_max          0.0010
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0562P)^2^+3.8585P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1090
_reflns_number_gt                2865
_reflns_number_total             3566
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ol071345q-file004.cif
_cod_data_source_block           RGK1263
_cod_original_formula_sum        'C13 H16 B Cl F5 I '
_cod_database_code               1505493