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_4127756
_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            'C19 H31 B O4'
_chemical_formula_weight         334.25
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 100.202(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   27.671(2)
_cell_length_b                   6.9365(6)
_cell_length_c                   10.7712(8)
_cell_measurement_reflns_used    5821
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      139.305
_cell_measurement_theta_min      6.491
_cell_volume                     2034.7(3)
_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 0.978
_diffrn_measured_fraction_theta_max 0.995
_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  0.0795
_diffrn_reflns_av_unetI/netI     0.0605
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            15883
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         66.987
_diffrn_reflns_theta_min         3.245
_exptl_absorpt_coefficient_mu    0.587
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.4247
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.091
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.142
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
; 
 Flack x determined using 1081 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_coef       0.012(2)
_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   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         3566
_refine_ls_number_restraints     86
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0729
_refine_ls_R_factor_gt           0.0572
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0938P)^2^+0.5309P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1513
_refine_ls_wR_factor_ref         0.1704
_reflns_Friedel_coverage         0.817
_reflns_Friedel_fraction_full    0.956
_reflns_Friedel_fraction_max     0.973
_reflns_number_gt                2831
_reflns_number_total             3566
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b05583_si_004.cif
_cod_data_source_block           cu_d8v18133_0m
_cod_original_cell_volume        2034.8(3)
_cod_database_code               4127756
_shelx_estimated_absorpt_t_min   0.892
_shelx_estimated_absorpt_t_max   0.933
_shelxl_version_number           2013-4
_shelx_res_checksum              30531
_shelx_hkl_checksum              22063