Ir/Zn Dual Catalysis: Enantioselective and Diastereodivergent α-Allylation of Unprotected α-Hydroxy Indanones.
He, Rui; Liu, Penglin; Huo, Xiaohong; Zhang, Wanbin; Organic letters 19 (2017) 5513–5516; doi:10.1021/acs.orglett.7b02577

data_1547612
_publ_section_title
;
 Ir/Zn Dual Catalysis: Enantioselective and Diastereodivergent
 \a-Allylation of Unprotected \a-Hydroxy Indanones.
;
_journal_issue                   20
_journal_name_full               'Organic letters'
_journal_page_first              5513
_journal_page_last               5516
_journal_paper_doi               10.1021/acs.orglett.7b02577
_journal_volume                  19
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         ' C19 H18 O2'
_chemical_formula_sum            'C19 H18 O2'
_chemical_formula_weight         278.33
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.8811(2)
_cell_length_b                   13.6299(4)
_cell_length_c                   18.7137(6)
_cell_measurement_reflns_used    9595
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      66.61
_cell_measurement_theta_min      4.01
_cell_volume                     1500.07(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            13670
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        66.614
_diffrn_reflns_theta_max         66.614
_diffrn_reflns_theta_min         4.012
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.621
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_description       block
_exptl_crystal_F_000             660
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.097
_refine_diff_density_min         -0.135
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 1002 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.12(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2637
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0295
_refine_ls_R_factor_gt           0.0278
_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^)+(0.0386P)^2^+0.1290P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0698
_refine_ls_wR_factor_ref         0.0711
_reflns_Friedel_coverage         0.695
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                2518
_reflns_number_total             2637
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b02577_si_003.cif
_cod_data_source_block           a
_cod_depositor_comments
'Adding full bibliography for 1547611--1547614.cif.'
_cod_original_formula_sum        ' C19 H18 O2'
_cod_database_code               1547612
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              1313
_shelx_hkl_checksum              2066