Highly Stereoselective Synthesis of Tetrasubstituted Acyclic All-Carbon Olefins via Enol Tosylation and Suzuki-Miyaura Coupling.
Li, Beryl X.; Le, Diane N.; Mack, Kyle A.; McClory, Andrew; Lim, Ngiap-Kie; Cravillion, Theresa; Savage, Scott; Han, Chong; Collum, David B.; Zhang, Haiming; Gosselin, Francis; Journal of the American Chemical Society 139 (2017) 10777–10783; doi:10.1021/jacs.7b05071

data_4131382
_publ_section_title
;
 Highly Stereoselective Synthesis of Tetrasubstituted Acyclic All-Carbon
 Olefins via Enol Tosylation and Suzuki-Miyaura Coupling.
;
_journal_issue                   31
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              10777
_journal_page_last               10783
_journal_paper_doi               10.1021/jacs.7b05071
_journal_volume                  139
_journal_year                    2017
_chemical_formula_sum            'C23 H22'
_chemical_formula_weight         298.40
_chemical_name_common            71452-153
_chemical_name_systematic        gene962
_space_group.centring_type       primitive
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                113.0060(10)
_cell_angle_beta                 90.5330(10)
_cell_angle_gamma                93.7970(10)
_cell_formula_units_Z            2
_cell_length_a                   9.3948(3)
_cell_length_b                   9.4545(3)
_cell_length_c                   10.5713(4)
_cell_measurement_reflns_used    7948
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.55
_cell_measurement_theta_min      4.72
_cell_volume                     861.76(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    ORTEP-32
_computing_publication_material  WinGX
_computing_structure_refinement  SHELXL-2016
_computing_structure_solution    SHELXT-2014
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.981
_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  0.0317
_diffrn_reflns_av_unetI/netI     0.0325
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_refln_scan_rate          8
_diffrn_refln_scan_width         2
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            11127
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.000
_diffrn_reflns_theta_max         68.248
_diffrn_reflns_theta_min         4.547
_diffrn_source                   'microfocus rotating anode'
_exptl_absorpt_coefficient_mu    0.483
_exptl_absorpt_correction_T_max  0.754
_exptl_absorpt_correction_T_min  0.701
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.150
_exptl_crystal_description       block
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3104
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0399
_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^)+(0.0546P)^2^+0.2703P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1048
_refine_ls_wR_factor_ref         0.1068
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2930
_reflns_number_total             3104
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja-2017-050714-File027.cif
_cod_data_source_block           71452-153
_cod_database_code               4131382
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.931
_shelx_estimated_absorpt_t_max   0.944
_shelx_res_checksum              46150
_shelx_hkl_checksum              64714