An Ir/Zn Dual Catalysis for Enantio- and Diastereodivergent α-Allylation of α-Hydroxyketones.
Huo, Xiaohong; He, Rui; Zhang, Xiao; Zhang, Wanbin; Journal of the American Chemical Society 138 (2016) 11093–11096; doi:10.1021/jacs.6b06156

data_4130729
_publ_section_title
;
 An Ir/Zn Dual Catalysis for Enantio- and Diastereodivergent \a-Allylation
 of \a-Hydroxyketones.
;
_journal_issue                   35
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              11093
_journal_page_last               11096
_journal_paper_doi               10.1021/jacs.6b06156
_journal_volume                  138
_journal_year                    2016
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C17 H15 N O4'
_chemical_formula_sum            'C17 H15 N O4'
_chemical_formula_weight         297.30
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-09-29
_audit_creation_method
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Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_cell_angle_alpha                68.426(7)
_cell_angle_beta                 85.638(5)
_cell_angle_gamma                87.899(6)
_cell_formula_units_Z            1
_cell_length_a                   6.4718(4)
_cell_length_b                   7.7276(6)
_cell_length_c                   7.9956(5)
_cell_measurement_reflns_used    3150
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      67.1543
_cell_measurement_theta_min      5.9598
_cell_volume                     370.76(5)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.2057659000
_diffrn_orient_matrix_UB_12      0.0354244000
_diffrn_orient_matrix_UB_13      -0.0928244000
_diffrn_orient_matrix_UB_21      0.1190633000
_diffrn_orient_matrix_UB_22      0.0183015000
_diffrn_orient_matrix_UB_23      -0.1799360000
_diffrn_orient_matrix_UB_31      -0.0219823000
_diffrn_orient_matrix_UB_32      -0.2106444000
_diffrn_orient_matrix_UB_33      0.0461554000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_av_unetI/netI     0.0202
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5939
_diffrn_reflns_theta_full        67.27
_diffrn_reflns_theta_max         67.27
_diffrn_reflns_theta_min         5.96
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.789
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.34221
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             156
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.025
_refine_ls_abs_structure_details 'Flack (1983), 1218 Friedel pairs'
_refine_ls_abs_structure_Flack   0.0(3)
_refine_ls_extinction_coef       0.029(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2535
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0394
_refine_ls_R_factor_gt           0.0366
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0581P)^2^+0.0279P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0983
_refine_ls_wR_factor_ref         0.1025
_reflns_number_gt                2370
_reflns_number_total             2535
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja6b06156_si_002.cif
_cod_data_source_block           150928_herui_ch2cl2_cu_2nd
_cod_original_cell_volume        370.77(4)
_cod_database_code               4130729
_chemical_oxdiff_formula         'c10 h10 n2 o8'
_reflns_odcompleteness_completeness 99.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C9(H9)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2A), C3(H3), C4(H4), C5(H5), C10(H10), C13(H13), C14(H14),
 C16(H16), C17(H17)
2.c X=CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;