Synthesis of Trisubstituted Alkenes via Direct Oxidative Arene-Alkene Coupling
Roderick C. Jones; Michał Gałęzowski; Donal F. O'Shea; Journal of Organic Chemistry 78 (2013) 8044–8053; doi:10.1021/jo401326f

data_4028509
_publ_section_title
;
 Synthesis of Trisubstituted Alkenes via Direct Oxidative Arene-Alkene
 Coupling
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8044
_journal_page_last               8053
_journal_paper_doi               10.1021/jo401326f
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C16 H11 F3 O2'
_chemical_formula_sum            'C16 H11 F3 O2'
_chemical_formula_weight         292.25
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   17.14511(5)
_cell_length_b                   15.82328(6)
_cell_length_c                   19.53876(7)
_cell_measurement_reflns_used    57131
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.2588
_cell_measurement_theta_min      3.4267
_cell_volume                     5300.71(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) 
(compiled Jul 11 2012,15:38:31) 
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) 
(compiled Jul 11 2012,15:38:31) 
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) 
(compiled Jul 11 2012,15:38:31) 
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.3196
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'SuperNova (Cu) x-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_sigmaI/netI    0.0097
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            105300
_diffrn_reflns_theta_full        76.45
_diffrn_reflns_theta_max         76.45
_diffrn_reflns_theta_min         4.42
_exptl_absorpt_coefficient_mu    1.071
_exptl_absorpt_correction_T_max  0.892
_exptl_absorpt_correction_T_min  0.760
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) 
(compiled Jul 11 2012,15:38:31) 
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) 
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.465
_exptl_crystal_description       block
_exptl_crystal_F_000             2400
_exptl_crystal_size_max          0.4383
_exptl_crystal_size_mid          0.2656
_exptl_crystal_size_min          0.1722
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     467
_refine_ls_number_reflns         5567
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0317
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0451P)^2^+1.9288P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0817
_refine_ls_wR_factor_ref         0.0831
_reflns_number_gt                5276
_reflns_number_total             5567
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo401326f_si_003.cif
_cod_data_source_block           osh109
_cod_database_code               4028509