Stereoselective Palladium-Catalyzed 1,3-Arylboration of Unconjugated Dienes for Expedient Synthesis of 1,3-Disubstituted Cyclohexanes
Pang, Hailiang; Wu, Dong; Cong, Hengjiang; Yin, Guoyin; ACS Catalysis 9 (2019) 8555–; doi:10.1021/acscatal.9b02747

data_4514821
_publ_section_title
;
 Stereoselective Palladium-Catalyzed 1,3-Arylboration of Unconjugated
 Dienes for Expedient Synthesis of 1,3-Disubstituted Cyclohexanes
;
_journal_issue                   9
_journal_name_full               'ACS Catalysis'
_journal_page_first              8555
_journal_paper_doi               10.1021/acscatal.9b02747
_journal_volume                  9
_journal_year                    2019
_chemical_formula_sum            'C14 H17 N O2'
_chemical_formula_weight         231.28
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/4
_cell_angle_alpha                90
_cell_angle_beta                 93.832(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.9605(11)
_cell_length_b                   9.5967(10)
_cell_length_c                   11.9487(13)
_cell_measurement_reflns_used    6941
_cell_measurement_temperature    253(2)
_cell_measurement_theta_max      69.90
_cell_measurement_theta_min      4.04
_cell_volume                     1254.0(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      253(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker Kappa APEX-Duo CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_unetI/netI     0.0741
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2306
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.640
_diffrn_reflns_theta_min         4.042
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.654
_exptl_absorpt_correction_T_max  0.753258
_exptl_absorpt_correction_T_min  0.363729
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'TWINABS-2012/1 (Bruker,2012)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_density_meas      ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.656
_refine_diff_density_min         -0.599
_refine_diff_density_rms         0.153
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.394
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2306
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.394
_refine_ls_R_factor_all          0.1319
_refine_ls_R_factor_gt           0.1290
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2936
_refine_ls_wR_factor_ref         0.3018
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2084
_reflns_number_total             2306
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs9b02747_si_003.cif
_cod_data_source_block           cu_1_1_0m_5
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_database_code               4514821
_shelx_shelxl_version_number     2016/4
_shelx_estimated_absorpt_t_min   0.950
_shelx_estimated_absorpt_t_max   0.974
_shelx_res_checksum              75980
_shelx_hkl_checksum              33494