Diastereoselective Aminooxygenation and Diamination of Alkenes with Amidines by Hypervalent Iodine(III) Reagents.
Chen, Hui; Kaga, Atsushi; Chiba, Shunsuke; Organic letters 16 (2014) 6136–; doi:10.1021/ol503000c

data_1518692
_publ_contact_author
;
Dr Shunsuke Chiba
Division of Chemistry and Biological Chemistry
School of Physical and Mathematical Sciences
Nanyang Technological University
21 Nanyang Link
Singapore 637371
Singapore
;
_publ_section_title
;
 Diastereoselective Aminooxygenation and Diamination of Alkenes with
 Amidines by Hypervalent Iodine(III) Reagents.
;
_journal_issue                   23
_journal_name_full               'Organic letters'
_journal_page_first              6136
_journal_paper_doi               10.1021/ol503000c
_journal_volume                  16
_journal_year                    2014
_chemical_formula_sum            'C24 H23 Cl3 N2 O'
_chemical_formula_weight         461.79
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 93.332(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.8866(4)
_cell_length_b                   11.3293(5)
_cell_length_c                   21.9439(11)
_cell_measurement_reflns_used    6927
_cell_measurement_temperature    103.(2)
_cell_measurement_theta_max      30.0307
_cell_measurement_theta_min      2.4263
_cell_volume                     2205.55(18)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      103.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0523
_diffrn_reflns_av_sigmaI/netI    0.0482
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            36479
_diffrn_reflns_theta_full        31.06
_diffrn_reflns_theta_max         31.06
_diffrn_reflns_theta_min         2.92
_exptl_absorpt_coefficient_mu    0.435
_exptl_absorpt_correction_T_max  0.85
_exptl_absorpt_correction_T_min  0.75
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.380
_refine_diff_density_max         0.476
_refine_diff_density_min         -0.524
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         7041
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0682
_refine_ls_R_factor_gt           0.0448
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0445P)^2^+1.1094P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0975
_refine_ls_wR_factor_ref         0.1073
_reflns_number_gt                5283
_reflns_number_total             7041
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol503000c_si_005.cif
_cod_data_source_block           I
_cod_database_code               1518692
_shelx_res_checksum              5138
_shelx_hkl_checksum              51155