#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/37/4023716.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_4023716
loop_
_publ_author_name
'Simon Specklin'
'Philippe Bertus'
'Jean-Marc Weibel'
'Patrick Pale'
_publ_section_title
;
 A Versatile and Highly Stereoselective Access to Vinyl Triflates
 Derived from 1,3-Dicarbonyl and Related Compounds
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7845
_journal_page_last               7848
_journal_paper_doi               10.1021/jo8015049
_journal_volume                  73
_journal_year                    2008
_chemical_formula_moiety         'C11 H9 F3 O4 S'
_chemical_formula_sum            'C11 H9 F3 O4 S'
_chemical_formula_weight         294.24
_chemical_name_systematic
;
 ?
;
_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   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            8
_cell_length_a                   7.8398(2)
_cell_length_b                   10.5404(3)
_cell_length_c                   29.6581(10)
_cell_measurement_reflns_used    26073
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.998
_cell_volume                     2450.79(12)
_computing_cell_refinement       'Denzo (Nonius B.V., 1998)'
_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo (Nonius B.V., 1998)'
_computing_molecular_graphics    'PLATON 98 (Spek, 1998)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'phi and omega 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  0.0603
_diffrn_reflns_av_sigmaI/netI    0.0390
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            13219
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         1.37
_exptl_absorpt_coefficient_mu    0.310
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.595
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.364
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.085
_refine_ls_extinction_coef       0.020(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2759
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0671
_refine_ls_R_factor_gt           0.0438
_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)+(0.0791P)²+0.2742P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1126
_refine_ls_wR_factor_ref         0.1354
_reflns_number_gt                1996
_reflns_number_total             2759
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            jo8015049_si_002.cif
_cod_data_source_block           pale3
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_database_code               4023716
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -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
C1 C 0.1974(2) 0.21120(17) 0.23107(7) 0.0367(5) Uani 1 1 d . . .
H1 H 0.2510 0.1394 0.2442 0.044 Uiso 1 1 calc R . .
C2 C 0.1850(3) 0.22002(19) 0.18490(8) 0.0444(5) Uani 1 1 d . . .
H2 H 0.2306 0.1548 0.1664 0.053 Uiso 1 1 calc R . .
C3 C 0.1056(3) 0.32445(19) 0.16537(8) 0.0462(5) Uani 1 1 d . . .
H3 H 0.0959 0.3303 0.1335 0.055 Uiso 1 1 calc R . .
C4 C 0.0411(3) 0.41955(19) 0.19237(8) 0.0429(5) Uani 1 1 d . . .
H4 H -0.0123 0.4912 0.1790 0.051 Uiso 1 1 calc R . .
C5 C 0.0535(2) 0.41139(17) 0.23884(7) 0.0374(5) Uani 1 1 d . . .
H5 H 0.0084 0.4772 0.2572 0.045 Uiso 1 1 calc R . .
C6 C 0.1320(2) 0.30669(16) 0.25879(7) 0.0329(4) Uani 1 1 d . . .
C7 C 0.1443(2) 0.29081(16) 0.30853(7) 0.0356(5) Uani 1 1 d . . .
C8 C 0.1028(3) 0.40177(18) 0.33764(7) 0.0401(5) Uani 1 1 d . . .
H8 H 0.1328 0.4834 0.3266 0.048 Uiso 1 1 calc R . .
C9 C 0.0280(3) 0.39644(17) 0.37735(7) 0.0382(5) Uani 1 1 d . . .
C10 C -0.0194(3) 0.50334(19) 0.40723(8) 0.0536(6) Uani 1 1 d . . .
H10A H 0.0094 0.5838 0.3925 0.080 Uiso 1 1 calc R . .
H10B H 0.0434 0.4964 0.4357 0.080 Uiso 1 1 calc R . .
H10C H -0.1422 0.5006 0.4133 0.080 Uiso 1 1 calc R . .
C11 C -0.0258(3) 0.2017(2) 0.47687(7) 0.0480(5) Uani 1 1 d . . .
O1 O 0.18770(19) 0.18999(12) 0.32518(5) 0.0449(4) Uani 1 1 d . . .
O2 O -0.03032(17) 0.27600(12) 0.39355(4) 0.0379(3) Uani 1 1 d . . .
O3 O 0.24958(18) 0.24448(15) 0.42885(5) 0.0485(4) Uani 1 1 d . . .
O4 O 0.0632(2) 0.06217(13) 0.40934(5) 0.0545(5) Uani 1 1 d . . .
F1 F 0.0584(2) 0.13447(14) 0.50746(4) 0.0652(4) Uani 1 1 d . . .
F2 F -0.18081(19) 0.15620(15) 0.47300(5) 0.0681(4) Uani 1 1 d . . .
F3 F -0.03313(19) 0.32068(12) 0.49039(4) 0.0570(4) Uani 1 1 d . . .
S1 S 0.08777(7) 0.18870(4) 0.422906(18) 0.0398(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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 120.73(18) . . ?
C2 C1 H1 119.6 . . ?
C6 C1 H1 119.6 . . ?
C1 C2 C3 120.0(2) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C4 C3 C2 119.8(2) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 120.48(19) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C4 C5 C6 120.16(19) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C5 C6 C1 118.8(2) . . ?
C5 C6 C7 122.56(18) . . ?
C1 C6 C7 118.59(16) . . ?
O1 C7 C6 121.16(17) . . ?
O1 C7 C8 120.67(19) . . ?
C6 C7 C8 118.16(16) . . ?
C9 C8 C7 125.60(18) . . ?
C9 C8 H8 117.2 . . ?
C7 C8 H8 117.2 . . ?
C8 C9 O2 118.69(17) . . ?
C8 C9 C10 127.92(19) . . ?
O2 C9 C10 113.16(18) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
F2 C11 F3 109.6(2) . . ?
F2 C11 F1 108.98(19) . . ?
F3 C11 F1 108.78(19) . . ?
F2 C11 S1 110.22(15) . . ?
F3 C11 S1 110.93(15) . . ?
F1 C11 S1 108.33(17) . . ?
C9 O2 S1 121.16(12) . . ?
O4 S1 O3 123.69(10) . . ?
O4 S1 O2 108.46(9) . . ?
O3 S1 O2 110.85(8) . . ?
O4 S1 C11 104.70(10) . . ?
O3 S1 C11 107.24(10) . . ?
O2 S1 C11 98.83(10) . . ?
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
C1 C2 1.376(3) . ?
C1 C6 1.397(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.391(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.379(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.384(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.395(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.488(3) . ?
C7 O1 1.220(2) . ?
C7 C8 1.490(3) . ?
C8 C9 1.317(3) . ?
C8 H8 0.9500 . ?
C9 O2 1.432(2) . ?
C9 C10 1.481(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 F2 1.311(3) . ?
C11 F3 1.318(2) . ?
C11 F1 1.327(3) . ?
C11 S1 1.837(2) . ?
O2 S1 1.5690(14) . ?
O3 S1 1.4093(16) . ?
O4 S1 1.4063(15) . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.4(3) . . . . ?
C1 C2 C3 C4 0.7(3) . . . . ?
C2 C3 C4 C5 -0.5(3) . . . . ?
C3 C4 C5 C6 0.2(3) . . . . ?
C4 C5 C6 C1 0.1(3) . . . . ?
C4 C5 C6 C7 -178.08(18) . . . . ?
C2 C1 C6 C5 0.1(3) . . . . ?
C2 C1 C6 C7 178.30(17) . . . . ?
C5 C6 C7 O1 167.80(18) . . . . ?
C1 C6 C7 O1 -10.4(3) . . . . ?
C5 C6 C7 C8 -12.4(3) . . . . ?
C1 C6 C7 C8 169.43(17) . . . . ?
O1 C7 C8 C9 -35.1(3) . . . . ?
C6 C7 C8 C9 145.1(2) . . . . ?
C7 C8 C9 O2 -4.6(3) . . . . ?
C7 C8 C9 C10 -178.6(2) . . . . ?
C8 C9 O2 S1 90.8(2) . . . . ?
C10 C9 O2 S1 -94.28(19) . . . . ?
C9 O2 S1 O4 -140.28(14) . . . . ?
C9 O2 S1 O3 -1.44(16) . . . . ?
C9 O2 S1 C11 110.90(15) . . . . ?
F2 C11 S1 O4 -49.73(19) . . . . ?
F3 C11 S1 O4 -171.25(16) . . . . ?
F1 C11 S1 O4 69.42(17) . . . . ?
F2 C11 S1 O3 177.28(16) . . . . ?
F3 C11 S1 O3 55.76(19) . . . . ?
F1 C11 S1 O3 -63.57(17) . . . . ?
F2 C11 S1 O2 62.11(17) . . . . ?
F3 C11 S1 O2 -59.41(18) . . . . ?
F1 C11 S1 O2 -178.73(14) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658754
