Rhodium(III)-Catalyzed Asymmetric Borylative Cyclization of Cyclohexadienone-Containing 1,6-Dienes: An Experimental and DFT Study.
Tan, Yun-Xuan; Zhang, Fang; Xie, Pei-Pei; Zhang, Shuo-Qing; Wang, Yi-Fan; Li, Qing-Hua; Tian, Ping; Hong, Xin; Lin, Guo-Qiang; Journal of the American Chemical Society 141 (2019) 12770–12779; doi:10.1021/jacs.9b05583

data_4127758
_publ_section_title
;
 Rhodium(III)-Catalyzed Asymmetric Borylative Cyclization of
 Cyclohexadienone-Containing 1,6-Dienes: An Experimental and DFT Study.
;
_journal_issue                   32
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12770
_journal_page_last               12779
_journal_paper_doi               10.1021/jacs.9b05583
_journal_volume                  141
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_sum            'C10 H14 O3'
_chemical_formula_weight         182.21
_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
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 95.124(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.9327(4)
_cell_length_b                   7.3133(4)
_cell_length_c                   8.9299(5)
_cell_measurement_reflns_used    4526
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      140.041
_cell_measurement_theta_min      9.945
_cell_volume                     450.94(4)
_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-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.941
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_Laue_measured_fraction_full 0.941
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            4584
_diffrn_reflns_point_group_measured_fraction_full 0.933
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         66.955
_diffrn_reflns_theta_min         4.972
_exptl_absorpt_coefficient_mu    0.807
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.5314
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             196
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.116
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details
; 
 Flack x determined using 674 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.01(8)
_refine_ls_extinction_coef       0.20(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   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         1521
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0306
_refine_ls_R_factor_gt           0.0305
_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^)+(0.0557P)^2^+0.0432P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0872
_refine_ls_wR_factor_ref         0.0874
_reflns_Friedel_coverage         0.826
_reflns_Friedel_fraction_full    0.922
_reflns_Friedel_fraction_max     0.931
_reflns_number_gt                1509
_reflns_number_total             1521
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b05583_si_005.cif
_cod_data_source_block           cu_d8v17722_0m
_cod_database_code               4127758
_shelx_estimated_absorpt_t_min   0.862
_shelx_estimated_absorpt_t_max   0.909
_shelxl_version_number           2013-4
_shelx_res_checksum              36474
_shelx_hkl_checksum              6215