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_4514822
_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         'C16 H21 N O2'
_chemical_formula_sum            'C16 H21 N O2'
_chemical_formula_weight         259.34
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-03-13
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   23.054(2)
_cell_length_b                   8.4318(9)
_cell_length_c                   7.3235(7)
_cell_measurement_reflns_used    3223
_cell_measurement_temperature    253(2)
_cell_measurement_theta_max      67.31
_cell_measurement_theta_min      3.83
_cell_volume                     1423.6(2)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_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    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      253(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_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  0.0618
_diffrn_reflns_av_unetI/netI     0.0712
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            4667
_diffrn_reflns_point_group_measured_fraction_full 0.829
_diffrn_reflns_point_group_measured_fraction_max 0.829
_diffrn_reflns_theta_full        64.995
_diffrn_reflns_theta_max         64.995
_diffrn_reflns_theta_min         3.835
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.627
_exptl_absorpt_correction_T_max  0.7530
_exptl_absorpt_correction_T_min  0.6496
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_density_diffrn    1.210
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.535
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.068
_refine_ls_abs_structure_details
;
 Flack x determined using 428 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.4(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2002
_refine_ls_number_restraints     27
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.1097
_refine_ls_R_factor_gt           0.1012
_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^)+(0.1308P)^2^+2.3092P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2707
_refine_ls_wR_factor_ref         0.2796
_reflns_Friedel_coverage         0.558
_reflns_Friedel_fraction_full    0.649
_reflns_Friedel_fraction_max     0.649
_reflns_number_gt                1735
_reflns_number_total             2002
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs9b02747_si_004.cif
_cod_data_source_block           cu_4_1_0m
_cod_database_code               4514822
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.940
_shelx_estimated_absorpt_t_min   0.912
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 C9-C10 = C11-C10 = C12-C11 = C13-C12 = C15-C14 = C16-C15 = C9-C16
 1.51 with sigma of 0.02
 C14-C13
 1.39 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C12) \\sim Ueq, Uanis(C13) \\sim Ueq, Uanis(C14) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
4.a Ternary CH refined with riding coordinates:
 C9(H9), C10(H10)
4.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C16(H16A,H16B), C11(H11A,H11B), C12(H12A,H12B)
4.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C8(H8), C13(H13), C14(H14), N1(H1)
4.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
4.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_olex2_submission_special_instructions 'No special instructions were received'