#------------------------------------------------------------------------------
#$Date: 2019-03-05 09:52:05 +0100 (mar 05 de mar de 2019) $
#$Revision: 213973 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/44/7204403.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_7204403
loop_
_publ_author_name
'Krasovsky, Arkady L.'
'Pissarev, Serge A.'
'Nenajdenko, Valentine G.'
'Balenkova, Elizabeth S.'
_publ_section_title
;
 ??-Trifluoroacetylvinyl phenyl sulfoxide???synthesis, Diels???Alder
 reaction and computational study
;
_journal_issue                   22
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 1'
_journal_page_first              2554
_journal_paper_doi               10.1039/b202583c
_journal_year                    2002
_chemical_formula_sum            'C10 H9 F3 O3 S'
_chemical_formula_weight         266.23
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_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                 90.92(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   19.913(4)
_cell_length_b                   5.1380(10)
_cell_length_c                   22.413(4)
_cell_measurement_reflns_used    24
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      13.5
_cell_measurement_theta_min      12.2
_cell_volume                     2292.8(8)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.587
_diffrn_measured_fraction_theta_max 0.587
_diffrn_measurement_device_type  CAD4
_diffrn_measurement_method       theta/2theta
_diffrn_radiation_monochromator  filter
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_av_sigmaI/netI    0.0198
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            1219
_diffrn_reflns_theta_full        24.98
_diffrn_reflns_theta_max         24.98
_diffrn_reflns_theta_min         2.76
_diffrn_standards_decay_%        .2
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.316
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.542
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prizm
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         1181
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.105
_refine_ls_R_factor_all          0.0318
_refine_ls_R_factor_gt           0.0318
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0667P)²+1.1611P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0890
_refine_ls_wR_factor_ref         0.0890
_reflns_number_gt                1181
_reflns_number_total             1181
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b202583c.txt
_cod_data_source_block           screw3
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7204403
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.58062(4) 0.52284(13) 0.34648(3) 0.0474(3) Uani 1 1 d . . .
F1 F 0.72185(10) 0.1857(5) 0.16118(10) 0.0837(7) Uani 1 1 d . . .
F2 F 0.70750(10) -0.0974(4) 0.22898(9) 0.0766(6) Uani 1 1 d . . .
F3 F 0.67784(10) -0.1831(4) 0.13894(10) 0.0809(6) Uani 1 1 d . . .
O1 O 0.58926(13) 0.2151(5) 0.13767(9) 0.0622(6) Uani 1 1 d . . .
O2 O 0.57011(11) -0.0946(4) 0.21020(10) 0.0533(6) Uani 1 1 d . . .
O3 O 0.50821(11) 0.5881(4) 0.35890(9) 0.0571(6) Uani 1 1 d . . .
C1 C 0.68014(16) 0.0046(6) 0.18002(14) 0.0566(7) Uani 1 1 d . . .
C2 C 0.60989(14) 0.1109(5) 0.19173(11) 0.0432(7) Uani 1 1 d . . .
C3 C 0.61288(15) 0.3091(5) 0.24140(11) 0.0437(7) Uani 1 1 d . . .
C4 C 0.57841(15) 0.2833(5) 0.29013(12) 0.0432(6) Uani 1 1 d . . .
C5 C 0.60637(14) 0.3142(6) 0.40623(12) 0.0467(7) Uani 1 1 d . . .
C6 C 0.66430(18) 0.1710(9) 0.40222(17) 0.0755(11) Uani 1 1 d . . .
C7 C 0.6835(2) 0.0131(10) 0.44941(19) 0.0938(14) Uani 1 1 d . . .
C8 C 0.6465(2) -0.0018(9) 0.49884(18) 0.0888(13) Uani 1 1 d . . .
C9 C 0.5892(3) 0.1395(12) 0.50206(18) 0.1099(18) Uani 1 1 d . . .
C10 C 0.5685(2) 0.2985(10) 0.45582(15) 0.0877(14) Uani 1 1 d . . .
H1 H 0.5628(19) 0.327(7) 0.1419(16) 0.065(12) Uiso 1 1 d . . .
H2 H 0.5537(17) -0.165(7) 0.1855(16) 0.058(11) Uiso 1 1 d . . .
H3 H 0.6375(16) 0.460(6) 0.2351(13) 0.055(8) Uiso 1 1 d . . .
H4 H 0.5516(15) 0.149(6) 0.2965(13) 0.051(8) Uiso 1 1 d . . .
H6 H 0.689(2) 0.179(8) 0.365(2) 0.101(13) Uiso 1 1 d . . .
H7 H 0.723(3) -0.063(10) 0.448(2) 0.117(17) Uiso 1 1 d . . .
H8 H 0.659(2) -0.105(10) 0.534(2) 0.114(15) Uiso 1 1 d . . .
H9 H 0.561(3) 0.095(12) 0.536(3) 0.15(2) Uiso 1 1 d . . .
H10 H 0.534(3) 0.411(10) 0.459(2) 0.127(18) Uiso 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 S1 C4 105.90(13) . . ?
O3 S1 C5 105.00(13) . . ?
C4 S1 C5 96.99(13) . . ?
F1 C1 F2 106.9(3) . . ?
F1 C1 F3 107.7(2) . . ?
F2 C1 F3 107.1(3) . . ?
F1 C1 C2 112.7(3) . . ?
F2 C1 C2 111.4(2) . . ?
F3 C1 C2 110.8(3) . . ?
O1 C2 O2 113.2(2) . . ?
O1 C2 C3 113.2(2) . . ?
O2 C2 C3 108.0(2) . . ?
O1 C2 C1 104.4(2) . . ?
O2 C2 C1 107.9(2) . . ?
C3 C2 C1 110.0(2) . . ?
C4 C3 C2 122.2(3) . . ?
C3 C4 S1 121.4(2) . . ?
C10 C5 C6 120.1(3) . . ?
C10 C5 S1 119.6(3) . . ?
C6 C5 S1 120.3(2) . . ?
C5 C6 C7 119.1(4) . . ?
C8 C7 C6 121.1(4) . . ?
C7 C8 C9 119.2(4) . . ?
C8 C9 C10 121.3(4) . . ?
C5 C10 C9 119.2(4) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O3 1.511(2) . ?
S1 C4 1.764(3) . ?
S1 C5 1.784(3) . ?
F1 C1 1.321(4) . ?
F2 C1 1.326(4) . ?
F3 C1 1.333(4) . ?
O1 C2 1.381(3) . ?
O2 C2 1.387(3) . ?
C1 C2 1.528(4) . ?
C2 C3 1.509(4) . ?
C3 C4 1.306(4) . ?
C5 C10 1.356(5) . ?
C5 C6 1.372(5) . ?
C6 C7 1.382(5) . ?
C7 C8 1.343(6) . ?
C8 C9 1.356(6) . ?
C9 C10 1.378(6) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9982267
