Conjugate Addition of Diethyl 1-Fluoro-1-phenylsulfonylmethanephosphonate to α,β-Unsaturated Compounds
Stanislav Opekar; Radek Pohl; Václav Eigner; Petr Beier; Journal of Organic Chemistry 78 (2013) 4573–4579; doi:10.1021/jo400297f

data_4028217
_publ_contact_author_address
; 
Institute of Organic Chemistry and Biochemistry AS CR, v.v.i.
Flemingovo n\'am\<est\'i 2
166 10 Praha 6
Czech Republic 
;
_publ_contact_author_email       petr.beier@uochb.cas.cz
_publ_contact_author_fax         '+420 220 183 578'
_publ_contact_author_name        'Beier, Petr'
_publ_contact_author_phone       '+420 220 183 409'
_publ_section_title
;
 Conjugate Addition of Diethyl 1-Fluoro-1-phenylsulfonylmethanephosphonate
 to \a,\b-Unsaturated Compounds
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4573
_journal_page_last               4579
_journal_paper_doi               10.1021/jo400297f
_journal_volume                  78
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C26 H28 F1 O6 P1 S1'
_chemical_formula_sum            'C26 H28 F O6 P S'
_chemical_formula_weight         518.54
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             12-04-05
_audit_creation_method           CRYSTALS_ver_14.11
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.099(3)
_cell_length_b                   9.3135(14)
_cell_length_c                   18.430(2)
_cell_measurement_reflns_used    3813
_cell_measurement_temperature    190
_cell_measurement_theta_max      75
_cell_measurement_theta_min      5
_cell_volume                     2591.7(7)
_computing_cell_refinement       'CrysAlis RED, (Oxford Diffraction, 2002)'
_computing_data_collection       'Xcalibur, (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis RED, (Oxford Diffraction, 2002)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_pressure         101
_diffrn_ambient_temperature      190
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Oxford Diffraction XCALIBUR'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.082
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            18755
_diffrn_reflns_theta_full        70.207
_diffrn_reflns_theta_max         75.491
_diffrn_reflns_theta_min         4.799
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.088
_exptl_absorpt_correction_T_max  0.39
_exptl_absorpt_correction_T_min  0.28
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
; 
 Analytical Absorption (De Meulenaer & Tompa, 1965) 
;
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_description       block
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.615
_exptl_crystal_size_mid          0.529
_exptl_crystal_size_min          0.445
_refine_diff_density_max         0.72
_refine_diff_density_min         -0.67
_refine_ls_abs_structure_details 'Flack (1983), 0 Friedel-pairs'
_refine_ls_abs_structure_Flack   0.13(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.9328
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         4302
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1099
_refine_ls_R_factor_gt           0.1032
_refine_ls_shift/su_max          0.0001911
_refine_ls_shift/su_mean         0.0000133
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] 
 where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ 
 A~i~ are: 
 32.1 27.5 26.4 13.7 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1120
_refine_ls_wR_factor_gt          0.1060
_refine_ls_wR_factor_ref         0.1060
_reflns_limit_h_max              18
_reflns_limit_h_min              0
_reflns_limit_k_max              11
_reflns_limit_k_min              0
_reflns_limit_l_max              22
_reflns_limit_l_min              -22
_reflns_number_gt                4302
_reflns_number_total             4749
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   3.42
_oxford_diffrn_Wilson_scale      0.05
_oxford_refine_ls_r_factor_ref   0.1032
_oxford_refine_ls_scale          4.60(2)
_oxford_reflns_number_all        4749
_oxford_reflns_threshold_expression_ref I>2.0\s(I)
_cod_data_source_file            jo400297f_si_002.cif
_cod_data_source_block           1
_cod_original_cell_volume        2591.7(8)
_cod_original_sg_symbol_Hall     'P 2c -2n '
_cod_original_sg_symbol_H-M      'P n a 21 '
_cod_original_formula_sum        'C26 H28 F1 O6 P1 S1'
_cod_database_code               4028217