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_4514823
_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_moiety         'C15 H18 O3'
_chemical_formula_sum            'C15 H18 O3'
_chemical_formula_weight         246.29
_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
_audit_creation_date             2018-11-29
_audit_creation_method
; 
Olex2 1.2 
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) 
;
_cell_angle_alpha                90
_cell_angle_beta                 96.027(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.827(2)
_cell_length_b                   20.383(3)
_cell_length_c                   5.0473(8)
_cell_measurement_reflns_used    1377
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      49.15
_cell_measurement_theta_min      3.46
_cell_volume                     1312.3(4)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.954
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1078
_diffrn_reflns_av_unetI/netI     0.0967
_diffrn_reflns_Laue_measured_fraction_full 0.954
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_number            8568
_diffrn_reflns_point_group_measured_fraction_full 0.954
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        53.189
_diffrn_reflns_theta_max         53.189
_diffrn_reflns_theta_min         3.465
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.693
_exptl_absorpt_correction_T_max  0.7505
_exptl_absorpt_correction_T_min  0.3676
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
SADABS-2008/1 (Bruker,2008) was used for absorption correction. 
wR2(int) was 0.1639 before and 0.0964 after correction. 
The Ratio of minimum to maximum transmission is 0.4898. 
The \l/2 correction factor is 0.0015. 
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_description       needle
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.572
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.117
_refine_ls_extinction_coef       0.016(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         1470
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.114
_refine_ls_R_factor_all          0.1428
_refine_ls_R_factor_gt           0.1184
_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^)+(0.1313P)^2^+4.1602P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2991
_refine_ls_wR_factor_ref         0.3188
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1088
_reflns_number_total             1470
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs9b02747_si_002.cif
_cod_data_source_block           cu_181019d_0m
_cod_database_code               4514823
_shelx_shelxl_version_number     2014/7
_olex2_refinement_description
; 
1. Fixed Uiso 
 At 1.2 times of: 
  All C(H) groups, {H1A,H1B,H1C} of C1, All C(H,H) groups, All O(H,H) groups 
 At 1.5 times of: 
  {H15A,H15B,H15C} of C15 
2. Others 
 Fixed Sof: H3A(0.68) H3B(0.32) 
3.a Riding coordinates: 
 O3(H3A,H3B), C1(H1A,H1B,H1C) 
3.b Ternary CH refined with riding coordinates: 
 C9(H9), C11(H11) 
3.c Secondary CH2 refined with riding coordinates: 
 C10(H10A,H10B), C14(H14A,H14B) 
3.d Aromatic/amide H refined with riding coordinates: 
 C4(H4), C5(H5), C7(H7), C8(H8), C13(H13) 
3.e Idealised Me refined as rotating group: 
 C15(H15A,H15B,H15C) 
;
_olex2_submission_special_instructions 'No special instructions were received'