Palladium-catalyzed enantioselective carboannulation of 1,3-dienes with aryl iodides enables access to chiral indanes.
Wu, Xiang; Chen, Shu-Sen; Zhang, Ling; Wang, Hai-Jun; Gong, Liu-Zhu; Chemical communications (Cambridge, England) 54 (2018) 9595–9598; doi:10.1039/c8cc04641g

data_7122068
_publ_section_title
;
 Palladium-catalyzed enantioselective carboannulation of 1,3-dienes with
 aryl iodides enables access to chiral indanes.
;
_journal_issue                   69
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              9595
_journal_page_last               9598
_journal_paper_doi               10.1039/c8cc04641g
_journal_volume                  54
_journal_year                    2018
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C12 H16 O3'
_chemical_formula_sum            'C12 H16 O3'
_chemical_formula_weight         208.25
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-08-16
_audit_creation_method
;
Olex2 1.2
(compiled 2017.07.20 svn.r3457 for OlexSys, GUI svn.r5375)
;
_audit_update_record
;
2018-01-17 deposited with the CCDC.
2018-07-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.415(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.8484(12)
_cell_length_b                   6.1584(6)
_cell_length_c                   13.6137(13)
_cell_measurement_reflns_used    9909
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      70.19
_cell_measurement_theta_min      4.45
_cell_volume                     1068.18(18)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0408
_diffrn_reflns_av_unetI/netI     0.0334
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14606
_diffrn_reflns_point_group_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.199
_diffrn_reflns_theta_min         3.274
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.749
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.6092
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1434 before and 0.0750 after correction. The Ratio of minimum to maximum transmission is 0.8087. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_description       prism
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Flack x determined using 1501 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.10(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     277
_refine_ls_number_reflns         3905
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.106
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0387
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0322P)^2^+0.3108P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0911
_refine_ls_wR_factor_ref         0.0942
_reflns_Friedel_coverage         0.774
_reflns_Friedel_fraction_full    0.944
_reflns_Friedel_fraction_max     0.925
_reflns_number_gt                3676
_reflns_number_total             3905
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc04641g2.cif
_cod_data_source_block           cu_d8v17262_0m
_cod_depositor_comments          'Adding full bibliography for 7122068.cif.'
_cod_database_code               7122068
_shelx_shelxl_version_number     2014/8
_shelx_estimated_absorpt_t_max   0.985
_shelx_estimated_absorpt_t_min   0.896
_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:
 C1(H1A), C1A(H1AB)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B), C2A(H2AB,H2AC),
 C10A(H10C,H10D), C11A(H11C,H11D), C12A(H12C,H12D)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C4A(H4A), C5A(H5A), C6A(H6A), C7A(H7A)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2), O3(H3), O1A(H1AA), O2A(H2AA), O3A(H3A)
;
_shelx_res_checksum              30163
_olex2_submission_special_instructions 'No special instructions were received'