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_4131387
_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 O'
_chemical_formula_weight         314.40
_chemical_name_common            71452-146
_chemical_name_systematic        gene958
_space_group.centring_type       primitive
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 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                90
_cell_angle_beta                 93.9290(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.8187(5)
_cell_length_b                   8.7228(4)
_cell_length_c                   15.7048(6)
_cell_measurement_reflns_used    9899
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.25
_cell_measurement_theta_min      2.82
_cell_volume                     1751.90(12)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0531
_diffrn_reflns_av_unetI/netI     0.0286
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_refln_scan_rate          2
_diffrn_refln_scan_width         1.25
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            22220
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.000
_diffrn_reflns_theta_max         68.304
_diffrn_reflns_theta_min         4.310
_diffrn_source                   'microfocus rotating anode'
_exptl_absorpt_coefficient_mu    0.545
_exptl_absorpt_correction_T_max  0.753
_exptl_absorpt_correction_T_min  0.682
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.192
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3219
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0357
_refine_ls_R_factor_gt           0.0343
_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^)+(0.0419P)^2^+0.5033P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0886
_refine_ls_wR_factor_ref         0.0901
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3059
_reflns_number_total             3219
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja-2017-050714-File028.cif
_cod_data_source_block           71452-146
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4131387
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.890
_shelx_estimated_absorpt_t_max   0.908
_shelx_res_checksum              37770
_shelx_hkl_checksum              2505