#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:54:20 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178449 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/70/4027081.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4027081
loop_
_publ_author_name
'José Luis García Ruano'
'José Antonio Fernández-Salas'
'M. Carmen Maestro'
_publ_section_title
;
 Stereocontrolled Fluorobenzylation of Vinyl Sulfones and
 α,β-Unsaturated Esters Mediated by a Remote Sulfinyl Group. Synthesis
 of Functionalized Enantiomerically Pure Benzylic Fluorides
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2893
_journal_page_last               2900
_journal_paper_doi               10.1021/jo300174k
_journal_volume                  77
_journal_year                    2012
_chemical_formula_sum            'C28 H24 F2 O3 S2'
_chemical_formula_weight         510.59
_chemical_name_systematic
;
?
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.4880(4)
_cell_length_b                   15.4600(10)
_cell_length_c                   28.8777(17)
_cell_measurement_reflns_used    2091
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.73
_cell_measurement_theta_min      2.63
_cell_volume                     2450.1(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0606
_diffrn_reflns_av_sigmaI/netI    0.0876
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            14074
_diffrn_reflns_theta_full        26.35
_diffrn_reflns_theta_max         26.35
_diffrn_reflns_theta_min         1.41
_exptl_absorpt_coefficient_mu    0.261
_exptl_absorpt_correction_T_max  0.9794
_exptl_absorpt_correction_T_min  0.9496
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_density_meas      0
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1064
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.430
_refine_diff_density_min         -0.427
_refine_diff_density_rms         0.132
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.14(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.148
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         4979
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.148
_refine_ls_R_factor_all          0.0810
_refine_ls_R_factor_gt           0.0491
_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/[σ²(Fo²)+(0.0725P)²+0.1196P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1062
_refine_ls_wR_factor_ref         0.1497
_reflns_number_gt                3803
_reflns_number_total             4979
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo300174k_si_001.cif
_cod_data_source_block           carmenmaestro00510_0m
_cod_database_code               4027081
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.6186(9) 0.3914(3) 0.52498(15) 0.0234(11) Uani 1 1 d .
H1 H 0.5873 0.4067 0.5563 0.028 Uiso 1 1 calc R
C2 C 0.8285(9) 0.4223(3) 0.50372(14) 0.0240(11) Uani 1 1 d .
H2 H 0.9361 0.4598 0.5199 0.029 Uiso 1 1 calc R
C3 C 0.8782(8) 0.3977(3) 0.45880(14) 0.0164(10) Uani 1 1 d .
H3 H 1.0224 0.4169 0.4438 0.020 Uiso 1 1 calc R
C4 C 0.7153(9) 0.3448(2) 0.43612(13) 0.0149(9) Uani 1 1 d .
C5 C 0.5015(8) 0.3157(3) 0.45714(14) 0.0192(10) Uani 1 1 d .
H5 H 0.3899 0.2802 0.4407 0.023 Uiso 1 1 calc R
C6 C 0.4559(9) 0.3398(3) 0.50225(14) 0.0217(10) Uani 1 1 d .
H6 H 0.3122 0.3205 0.5174 0.026 Uiso 1 1 calc R
C7 C 0.6057(8) 0.3622(3) 0.33784(13) 0.0139(9) Uani 1 1 d .
H7A H 0.6045 0.3283 0.3088 0.017 Uiso 1 1 calc R
H7B H 0.4362 0.3645 0.3495 0.017 Uiso 1 1 calc R
C8 C 0.6908(9) 0.4556(2) 0.32674(13) 0.0148(9) Uani 1 1 d .
H8 H 0.8655 0.4525 0.3170 0.018 Uiso 1 1 calc R
C9 C 0.6752(8) 0.5177(2) 0.36720(12) 0.0150(9) Uani 1 1 d .
C10 C 0.4763(8) 0.5194(3) 0.39699(13) 0.0170(9) Uani 1 1 d .
H10 H 0.3454 0.4804 0.3918 0.020 Uiso 1 1 calc R
C11 C 0.4630(9) 0.5766(3) 0.43433(13) 0.0204(10) Uani 1 1 d .
H11 H 0.3268 0.5768 0.4547 0.024 Uiso 1 1 calc R
C12 C 0.6539(9) 0.6326(3) 0.44051(14) 0.0225(11) Uani 1 1 d .
C13 C 0.8534(9) 0.6345(3) 0.41200(14) 0.0204(10) Uani 1 1 d .
H13 H 0.9826 0.6742 0.4173 0.025 Uiso 1 1 calc R
C14 C 0.8618(8) 0.5763(2) 0.37495(14) 0.0184(10) Uani 1 1 d .
H14 H 0.9981 0.5771 0.3547 0.022 Uiso 1 1 calc R
C15 C 0.5418(8) 0.4880(3) 0.28457(13) 0.0167(9) Uani 1 1 d .
H15 H 0.5406 0.4426 0.2599 0.020 Uiso 1 1 calc R
C16 C 0.6478(8) 0.5709(3) 0.26548(13) 0.0154(10) Uani 1 1 d .
C17 C 0.5651(10) 0.6509(3) 0.28073(14) 0.0239(11) Uani 1 1 d .
H17 H 0.4352 0.6534 0.3024 0.029 Uiso 1 1 calc R
C18 C 0.6684(11) 0.7272(3) 0.26490(15) 0.0304(13) Uani 1 1 d .
H18 H 0.6095 0.7811 0.2760 0.037 Uiso 1 1 calc R
C19 C 0.8546(11) 0.7256(3) 0.23341(16) 0.0316(14) Uani 1 1 d .
H19 H 0.9232 0.7780 0.2223 0.038 Uiso 1 1 calc R
C20 C 0.9421(10) 0.6465(3) 0.21790(14) 0.0244(11) Uani 1 1 d .
H20 H 1.0748 0.6447 0.1968 0.029 Uiso 1 1 calc R
C21 C 0.8370(8) 0.5701(3) 0.23303(13) 0.0172(10) Uani 1 1 d .
C22 C 0.7140(10) 0.4569(3) 0.16525(14) 0.0209(10) Uani 1 1 d .
C23 C 0.5911(8) 0.5224(3) 0.14302(13) 0.0198(10) Uani 1 1 d .
H23 H 0.6285 0.5811 0.1497 0.024 Uiso 1 1 calc R
C24 C 0.4117(10) 0.5025(3) 0.11069(14) 0.0222(11) Uani 1 1 d .
H24 H 0.3256 0.5479 0.0958 0.027 Uiso 1 1 calc R
C25 C 0.3562(10) 0.4166(3) 0.09978(14) 0.0268(12) Uani 1 1 d .
C26 C 0.4857(10) 0.3525(3) 0.12283(15) 0.0304(12) Uani 1 1 d .
H26 H 0.4511 0.2937 0.1160 0.037 Uiso 1 1 calc R
C27 C 0.6637(10) 0.3712(3) 0.15556(15) 0.0284(12) Uani 1 1 d .
H27 H 0.7490 0.3261 0.1709 0.034 Uiso 1 1 calc R
C28 C 0.1654(11) 0.3956(3) 0.06420(15) 0.0364(14) Uani 1 1 d .
H28A H 0.2136 0.3436 0.0471 0.055 Uiso 1 1 calc R
H28B H 0.1492 0.4442 0.0426 0.055 Uiso 1 1 calc R
H28C H 0.0091 0.3855 0.0797 0.055 Uiso 1 1 calc R
F1 F 0.3021(5) 0.50424(15) 0.29946(8) 0.0233(6) Uani 1 1 d .
F2 F 0.6464(5) 0.68810(17) 0.47694(9) 0.0342(7) Uani 1 1 d .
O1 O 0.9562(7) 0.40003(18) 0.23761(9) 0.0263(8) Uani 1 1 d .
O2 O 1.0404(6) 0.32903(18) 0.37113(9) 0.0212(7) Uani 1 1 d .
O3 O 0.7185(6) 0.21673(16) 0.37738(10) 0.0231(7) Uani 1 1 d .
S1 S 0.9596(2) 0.47577(7) 0.20560(4) 0.0206(3) Uani 1 1 d .
S2 S 0.7898(2) 0.30679(6) 0.37938(3) 0.0160(2) Uani 1 1 d .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C6 C1 C2 122.0(4)
C3 C2 C1 119.0(4)
C4 C3 C2 118.9(4)
C3 C4 C5 122.0(4)
C3 C4 S2 118.8(3)
C5 C4 S2 119.0(3)
C6 C5 C4 118.5(4)
C1 C6 C5 119.6(4)
C8 C7 S2 114.5(3)
C9 C8 C15 111.9(3)
C9 C8 C7 114.4(3)
C15 C8 C7 107.7(3)
C14 C9 C10 117.9(4)
C14 C9 C8 119.8(4)
C10 C9 C8 122.3(4)
C9 C10 C11 122.1(4)
C12 C11 C10 117.4(4)
F2 C12 C13 118.4(4)
F2 C12 C11 118.4(4)
C13 C12 C11 123.1(4)
C12 C13 C14 118.2(4)
C9 C14 C13 121.3(4)
F1 C15 C16 108.6(3)
F1 C15 C8 108.1(3)
C16 C15 C8 110.9(3)
C17 C16 C21 117.6(4)
C17 C16 C15 120.9(4)
C21 C16 C15 121.5(4)
C18 C17 C16 121.3(4)
C19 C18 C17 120.6(4)
C18 C19 C20 119.3(4)
C21 C20 C19 120.4(4)
C20 C21 C16 120.9(4)
C20 C21 S1 113.5(3)
C16 C21 S1 125.6(3)
C23 C22 C27 120.9(4)
C23 C22 S1 123.3(3)
C27 C22 S1 115.7(4)
C22 C23 C24 119.8(4)
C23 C24 C25 121.0(4)
C26 C25 C24 117.3(4)
C26 C25 C28 122.0(4)
C24 C25 C28 120.7(4)
C25 C26 C27 122.5(4)
C22 C27 C26 118.5(4)
O1 S1 C21 111.14(17)
O1 S1 C22 105.3(2)
C21 S1 C22 97.8(2)
O2 S2 O3 118.82(19)
O2 S2 C7 108.37(19)
O3 S2 C7 106.3(2)
O2 S2 C4 107.0(2)
O3 S2 C4 106.90(19)
C7 S2 C4 109.2(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.366(7)
C1 C2 1.390(7)
C2 C3 1.379(6)
C3 C4 1.378(6)
C4 C5 1.395(6)
C4 S2 1.788(4)
C5 C6 1.377(6)
C7 C8 1.552(5)
C7 S2 1.787(4)
C8 C9 1.514(5)
C8 C15 1.549(5)
C9 C14 1.386(6)
C9 C10 1.390(6)
C10 C11 1.397(5)
C11 C12 1.370(7)
C12 F2 1.359(5)
C12 C13 1.370(7)
C13 C14 1.398(6)
C15 F1 1.407(5)
C15 C16 1.513(6)
C16 C17 1.389(6)
C16 C21 1.399(6)
C17 C18 1.386(6)
C18 C19 1.368(7)
C19 C20 1.389(7)
C20 C21 1.384(6)
C21 S1 1.791(4)
C22 C23 1.375(6)
C22 C27 1.383(6)
C22 S1 1.806(5)
C23 C24 1.391(6)
C24 C25 1.398(6)
C25 C26 1.389(7)
C25 C28 1.502(7)
C26 C27 1.390(7)
O1 S1 1.492(3)
O2 S2 1.437(3)
O3 S2 1.448(3)
