Enantioselective iridium-catalyzed carbonyl isoprenylation via alcohol-mediated hydrogen transfer.
Xiang, Ming; Luo, Guoshun; Wang, Yuankai; Krische, Michael J.; Chemical communications (Cambridge, England) 55 (2019) 981–; doi:10.1039/c8cc09706b

data_7122870
_publ_section_title
;
 Enantioselective iridium-catalyzed carbonyl isoprenylation via
 alcohol-mediated hydrogen transfer.
;
_journal_issue                   7
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              981
_journal_paper_doi               10.1039/c8cc09706b
_journal_volume                  55
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C12 H12 Cl2 O'
_chemical_formula_sum            'C12 H12 Cl2 O'
_chemical_formula_weight         243.12
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_block_doi                 10.5517/ccdc.csd.cc20w2bb
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2018-10-12 deposited with the CCDC.
2018-12-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 112.794(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.442(2)
_cell_length_b                   4.8336(11)
_cell_length_c                   12.394(3)
_cell_measurement_reflns_used    7154
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.6
_cell_measurement_theta_min      2.17
_cell_volume                     576.7(2)
_computing_cell_refinement       'Apex II release 2010, Bruker AXS, Inc.'
_computing_data_collection       'Apex II release 2010, Bruker AXS, Inc.'
_computing_data_reduction        'Apex II release 2010, Bruker AXS, Inc.'
_computing_molecular_graphics    'XP SHELXTL/PC, Siemens Analytical'
_computing_publication_material  'SHELXL-2016/6, Sheldrick, G. M.'
_computing_structure_refinement  'Shelxl-2016/6, Sheldrick, G. M.'
_computing_structure_solution
;

Sheldrick, G. M. (2015).  SHELXT.  Acta Cryst. A71, 3-8.

;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Nonius Kappa CCD with Bruker Apex II detector'
_diffrn_measurement_method       \w-scans
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14723
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.603
_diffrn_reflns_theta_min         3.253
_diffrn_source                   'fine focus sealed tube'
_exptl_absorpt_coefficient_mu    0.532
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.887
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS. G. M. Sheldrick. Apex II release 2010, Bruker AXS, Inc.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_description       lath
_exptl_crystal_F_000             252
_exptl_crystal_size_max          0.490
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.352
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.00(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     141
_refine_ls_number_reflns         3482
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0305
_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^)+(0.0347P)^2^+0.0770P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0648
_refine_ls_wR_factor_ref         0.0660
_reflns_Friedel_coverage         0.807
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                3308
_reflns_number_total             3482
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc09706b2.cif
_cod_data_source_block           shelx
_cod_database_code               7122870
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.781
_shelx_estimated_absorpt_t_max   0.939
_shelx_res_checksum              93507