Catalytic Regio- and Enantioselective Haloazidation of Allylic Alcohols.
Seidl, Frederick J.; Min, Chang; Lopez, Jovan A.; Burns, Noah Z.; Journal of the American Chemical Society 140 (2018) 15646–15650; doi:10.1021/jacs.8b10799

data_4133530
_publ_section_title
;
 Catalytic Regio- and Enantioselective Haloazidation of Allylic Alcohols.
;
_journal_issue                   46
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15646
_journal_page_last               15650
_journal_paper_doi               10.1021/jacs.8b10799
_journal_volume                  140
_journal_year                    2018
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C23 H24 Cl Fe N3 O'
_chemical_formula_sum            'C23 H24 Cl Fe N3 O'
_chemical_formula_weight         449.75
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/1
_cell_angle_alpha                90
_cell_angle_beta                 95.891(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.2168(2)
_cell_length_b                   10.3152(3)
_cell_length_c                   14.2483(4)
_cell_measurement_reflns_used    1910
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      71.07
_cell_measurement_theta_min      3.12
_cell_volume                     1055.08(5)
_computing_cell_refinement       'Bruker SAINT (Bruker, 2015)'
_computing_data_collection       'Bruker APEX-3 (Bruker, 2015)'
_computing_data_reduction        'Bruker SAINT (Bruker, 2015)'
_computing_molecular_graphics    'Bruker XP (Bruker, 2015)'
_computing_publication_material  'CIFTAB (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT-2014/2 (Sheldrick, 2015)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       'combination of \w and \f-scans '
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0835
_diffrn_reflns_av_unetI/netI     0.0856
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13097
_diffrn_reflns_point_group_measured_fraction_full 0.928
_diffrn_reflns_point_group_measured_fraction_max 0.912
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.099
_diffrn_reflns_theta_min         3.118
_diffrn_source                   'Incoatec micro-focus'
_exptl_absorpt_coefficient_mu    7.041
_exptl_absorpt_correction_T_max  0.7755
_exptl_absorpt_correction_T_min  0.5915
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_description       block
_exptl_crystal_F_000             468
_exptl_crystal_size_max          0.137
_exptl_crystal_size_mid          0.065
_exptl_crystal_size_min          0.063
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.386
_refine_diff_density_rms         0.066
_refine_ls_abs_structure_details
;
 Flack x determined using 1076 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.026(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.938
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3780
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.938
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0427
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0238P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0840
_refine_ls_wR_factor_ref         0.0866
_reflns_Friedel_coverage         0.747
_reflns_Friedel_fraction_full    0.856
_reflns_Friedel_fraction_max     0.828
_reflns_number_gt                3159
_reflns_number_total             3780
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b10799_si_002.cif
_cod_data_source_block           su1803
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4133530
_shelx_shelxl_version_number     2018/1
_shelx_estimated_absorpt_t_min   0.445
_shelx_estimated_absorpt_t_max   0.665
_diffrn_source_monochromator     'MONTEL Multi-layer'
_shelx_res_checksum              34046
_shelx_hkl_checksum              20869