Iridium-catalysed asymmetric allylic alkylation of benzofuran γ-lactones followed by heteroaromatic Cope rearrangement: study of an unusual reaction sequence.
Bos, Maxence; Riguet, Emmanuel; Chemical communications (Cambridge, England) 53 (2017) 4997–5000; doi:10.1039/c7cc01529a

data_7119993
_publ_section_title
;
 Iridium-catalysed asymmetric allylic alkylation of benzofuran \g-lactones
 followed by heteroaromatic Cope rearrangement: study of an unusual
 reaction sequence.
;
_journal_issue                   36
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              4997
_journal_page_last               5000
_journal_paper_doi               10.1039/c7cc01529a
_journal_volume                  53
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_sum            'C21 H16 Cl2 O3'
_chemical_formula_weight         387.24
_chemical_name_systematic        (S)-21
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2017-02-20 deposited with the CCDC.
2017-04-06 downloaded from the CCDC.
;
_cell_angle_alpha                90.000(0)
_cell_angle_beta                 98.0371(8)
_cell_angle_gamma                90.000(0)
_cell_formula_units_Z            4
_cell_length_a                   8.0715(2)
_cell_length_b                   8.9946(2)
_cell_length_c                   25.1406(6)
_cell_measurement_reflns_used    9253
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.63
_cell_measurement_theta_min      3.55
_cell_volume                     1807.28(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  CMOS
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_radiation_source         microsource
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_av_sigmaI/netI    0.0281
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            40507
_diffrn_reflns_theta_full        74.61
_diffrn_reflns_theta_max         74.61
_diffrn_reflns_theta_min         3.55
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.384
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.074(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     493
_refine_ls_number_reflns         7306
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0250
_refine_ls_R_factor_gt           0.0242
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0237P)^2^+0.4258P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0584
_refine_ls_wR_factor_ref         0.0588
_reflns_number_gt                7151
_reflns_number_total             7306
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7cc01529a2.cif
_cod_data_source_block           cu_16er005_0m
_cod_depositor_comments
;
Adding full bibliography for 7119993--7119996.cif.

2017-11-19
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_sg_symbol_H-M      P2(1)
_cod_original_formula_sum        'C42 H32 Cl4 O6'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     774.48
_cod_database_code               7119993