Interaction of a C-F Bond with the π-System of a C=C Bond or "Head On" with a Proximate C-H Bond
Michael T. Scerba; Steven Bloom; Nathan Haselton; Maxime Siegler; Jake Jaffe; Thomas Lectka; Journal of Organic Chemistry 77 (2012) 1605–1609; doi:10.1021/jo2024152

data_4026937
_publ_section_title
;
 Interaction of a C-F Bond with the \p-System of a C=C Bond or "Head On"
 with a Proximate C-H Bond
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1605
_journal_page_last               1609
_journal_paper_doi               10.1021/jo2024152
_journal_volume                  77
_journal_year                    2012
_chemical_formula_moiety         'C14 H13 F O3'
_chemical_formula_sum            'C14 H13 F O3'
_chemical_formula_weight         248.24
_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            8
_cell_length_a                   11.8147(3)
_cell_length_b                   13.0024(3)
_cell_length_c                   14.1560(3)
_cell_measurement_reflns_used    6389
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      28.95
_cell_measurement_theta_min      1.72
_cell_volume                     2174.64(9)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.31 (release 08-01-2009 CrysAlis171 .NET)
(compiled Jan  8 2009,16:24:04)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.31 (release 08-01-2009 CrysAlis171 .NET)
(compiled Jan  8 2009,16:24:04)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.31 (release 08-01-2009 CrysAlis171 .NET)
(compiled Jan  8 2009,16:24:04)
;
_computing_molecular_graphics    'SHELXTL v6.10 (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL v6.10 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 2008)'
_diffrn_ambient_temperature      110(2)
_diffrn_detector_area_resol_mean 15.9890
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Goniometer KM4/Xcalibur, detector: Sapphire3'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) x-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_av_sigmaI/netI    0.0271
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12166
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.74
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_correction_T_min  0.959
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.31 (release 08-01-2009 CrysAlis171 .NET)
(compiled Jan  8 2009,16:24:04)
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            colorless
_exptl_crystal_density_diffrn    1.516
_exptl_crystal_description       'thick plate'
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2137
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0393
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0559P)^2^+0.4668P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0957
_refine_ls_wR_factor_ref         0.1012
_reflns_number_gt                1694
_reflns_number_total             2137
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo2024152_si_002.cif
_cod_data_source_block           1
_cod_database_code               4026937