Synthetic Applications of α-Fluoroalkylated Enones. 1. Use as Dienophiles in Diels-Alder Cycloadditions
Julia Leuger; Gaëlle Blond; Roland Fröhlich; Thierry Billard; Günter Haufe; Bernard R. Langlois; Journal of Organic Chemistry 71 (2006) 2735–2739; doi:10.1021/jo052567+

data_4021610
_publ_section_title
;
 Synthetic Applications of \a-Fluoroalkylated Enones.
 1. Use as Dienophiles in Diels-Alder Cycloadditions
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2735
_journal_page_last               2739
_journal_paper_doi               10.1021/jo052567+
_journal_volume                  71
_journal_year                    2006
_chemical_formula_sum            'C20 H20 F6 O'
_chemical_formula_weight         390.36
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 108.96(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.208(4)
_cell_length_b                   13.751(1)
_cell_length_c                   11.681(2)
_cell_measurement_reflns_used    18
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      44.57
_cell_measurement_theta_min      22.04
_cell_volume                     1702.6(7)
_computing_cell_refinement       'Express (Nonius B.V., 1994)'
_computing_data_collection       'Express (Nonius B.V., 1994)'
_computing_data_reduction        'MolEN (Fair, 1990)'
_computing_molecular_graphics    'SCHAKAL (Keller, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      223(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Enraf Nonius CAD4'
_diffrn_measurement_method       '\w/2\q scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_av_sigmaI/netI    0.0454
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3635
_diffrn_reflns_theta_full        74.24
_diffrn_reflns_theta_max         74.24
_diffrn_reflns_theta_min         4.17
_diffrn_standards_decay_%        12.5
_diffrn_standards_interval_count 250
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.199
_exptl_absorpt_correction_T_max  0.7537
_exptl_absorpt_correction_T_min  0.5855
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'based on \y scan data'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.523
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       pyramide
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       0.0167(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3458
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.0748
_refine_ls_R_factor_gt           0.0460
_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^)+(0.0927P)^2^+0.1016P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1304
_refine_ls_wR_factor_ref         0.1425
_reflns_number_gt                2555
_reflns_number_total             3458
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo052567+si20051219_115154.cif
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4021610