Hydroarylation of alkenes by protonation/Friedel-Crafts trapping - HFIP-mediated access to per-aryl quaternary stereocentres.
Nielsen, Christian D.-T.; White, Andrew J. P.; Sale, David; Burés, Jordi; Spivey, Alan Christopher; The Journal of organic chemistry  (2019) –; doi:10.1021/acs.joc.9b02393

data_4033666
_publ_section_title
;
 Hydroarylation of alkenes by protonation/Friedel-Crafts trapping -
 HFIP-mediated access to per-aryl quaternary stereocentres.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b02393
_journal_year                    2019
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C24 H26 O, 0.25(C7 H16)'
_chemical_formula_sum            'C25.75 H30 O'
_chemical_formula_weight         355.50
_space_group_crystal_system      hexagonal
_space_group_IT_number           169
_space_group_name_Hall           'P 61'
_space_group_name_H-M_alt        'P 61'
_symmetry_space_group_name_Hall  'P 61'
_symmetry_space_group_name_H-M   'P 61'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            6
_cell_length_a                   23.9466(8)
_cell_length_b                   23.9466(8)
_cell_length_c                   6.5821(4)
_cell_measurement_reflns_used    1092
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      55.7610
_cell_measurement_theta_min      3.6600
_cell_volume                     3268.8(3)
_computing_cell_refinement       'CrysAlisPro, Rigaku OD'
_computing_data_collection       'CrysAlisPro, Rigaku OD'
_computing_data_reduction        'CrysAlisPro, Rigaku OD'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'CIFTAB-2014 (Sheldrick, 2017)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2017)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 10.4115
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Agilent Xcalibur PX Ultra A'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0427
_diffrn_reflns_av_unetI/netI     0.0689
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            5986
_diffrn_reflns_point_group_measured_fraction_full 0.874
_diffrn_reflns_point_group_measured_fraction_max 0.843
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.947
_diffrn_reflns_theta_min         3.692
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.484
_exptl_absorpt_correction_T_max  0.961
_exptl_absorpt_correction_T_min  0.907
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
; 
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015) 
Analytical numeric absorption correction using a multifaceted crystal 
model based on expressions derived by R.C. Clark & J.S. Reid. 
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) 
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.084
_exptl_crystal_description       'blocky needles'
_exptl_crystal_F_000             1155
_exptl_crystal_size_max          0.369
_exptl_crystal_size_mid          0.129
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
; 
 Flack x determined using 405 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.9(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.966
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3670
_refine_ls_number_restraints     155
_refine_ls_restrained_S_all      0.989
_refine_ls_R_factor_all          0.1363
_refine_ls_R_factor_gt           0.0867
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1685P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2306
_refine_ls_wR_factor_ref         0.3024
_reflns_Friedel_coverage         0.578
_reflns_Friedel_fraction_full    0.723
_reflns_Friedel_fraction_max     0.680
_reflns_number_gt                1864
_reflns_number_total             3670
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b02393_si_002.cif
_cod_data_source_block           20
_cod_database_code               4033666
_shelx_shelxl_version_number     2018/3
_shelx_res_checksum              47287
_shelx_hkl_checksum              9847
_shelx_fab_checksum              22243