#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:38:07 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178475 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/96/4029625.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_4029625
loop_
_publ_author_name
'Wang, Wengui'
'Shen, Haiming'
'Wan, Xiao-Long'
'Chen, Qing-Yun'
'Guo, Yong'
_publ_section_title
;
 Enantioselective Pd-Catalyzed Allylation of Acyclic α-Fluorinated
 Ketones.
;
_journal_issue                   13
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              6347
_journal_page_last               6353
_journal_paper_doi               10.1021/jo500923u
_journal_volume                  79
_journal_year                    2014
_chemical_formula_sum            'C16 H15 F O3 S'
_chemical_formula_weight         306.34
_chemical_name_systematic
; 
 ? 
;
_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                 93.774(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.4436(15)
_cell_length_b                   9.3132(16)
_cell_length_c                   17.109(3)
_cell_measurement_reflns_used    2116
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      44.699
_cell_measurement_theta_min      6.151
_cell_volume                     1501.5(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_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  0.0520
_diffrn_reflns_av_sigmaI/netI    0.0544
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8465
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.16
_exptl_absorpt_coefficient_mu    0.233
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62694
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.212
_exptl_crystal_size_mid          0.175
_exptl_crystal_size_min          0.121
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       0.0064(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2938
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0716
_refine_ls_R_factor_gt           0.0463
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0635P)²+0.0620P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1117
_refine_ls_wR_factor_ref         0.1266
_reflns_number_gt                2027
_reflns_number_total             2938
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo500923u_si_001.cif
_cod_data_source_block           cd213624
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

 Adding full bibliography for 4029625.cif.
;
_cod_original_cell_volume        1501.4(4)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4029625
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -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
S1 S 0.68997(6) 0.24945(7) 1.02728(3) 0.0565(2) Uani 1 1 d .
F1 F 1.04837(13) 0.36041(16) 1.08951(7) 0.0749(4) Uani 1 1 d .
O1 O 0.81436(14) 0.35083(15) 1.00213(8) 0.0551(4) Uani 1 1 d .
O2 O 0.74784(16) 0.11548(19) 1.05186(8) 0.0695(5) Uani 1 1 d .
O3 O 0.61749(17) 0.3350(2) 1.07987(8) 0.0844(6) Uani 1 1 d .
C1 C 0.9374(2) 0.2868(2) 0.97364(11) 0.0462(5) Uani 1 1 d .
C2 C 1.0548(2) 0.2991(2) 1.01827(12) 0.0544(5) Uani 1 1 d .
C3 C 1.2012(2) 0.2619(3) 1.00173(16) 0.0783(8) Uani 1 1 d .
H3A H 1.2043 0.2363 0.9475 0.117 Uiso 1 1 calc R
H3B H 1.2329 0.1822 1.0339 0.117 Uiso 1 1 calc R
H3C H 1.2619 0.3430 1.0130 0.117 Uiso 1 1 calc R
C4 C 0.9197(2) 0.2192(2) 0.89597(11) 0.0480(5) Uani 1 1 d .
C5 C 0.9657(2) 0.0810(3) 0.88404(13) 0.0633(6) Uani 1 1 d .
H5 H 1.0117 0.0305 0.9252 0.076 Uiso 1 1 calc R
C6 C 0.9441(3) 0.0174(3) 0.81170(16) 0.0826(8) Uani 1 1 d .
H6 H 0.9756 -0.0759 0.8042 0.099 Uiso 1 1 calc R
C7 C 0.8768(3) 0.0903(4) 0.75089(15) 0.0826(9) Uani 1 1 d .
H7 H 0.8624 0.0469 0.7021 0.099 Uiso 1 1 calc R
C8 C 0.8308(3) 0.2268(3) 0.76201(13) 0.0754(8) Uani 1 1 d .
H8 H 0.7842 0.2762 0.7206 0.091 Uiso 1 1 calc R
C9 C 0.8524(2) 0.2925(3) 0.83394(12) 0.0606(6) Uani 1 1 d .
H9 H 0.8218 0.3863 0.8407 0.073 Uiso 1 1 calc R
C10 C 0.5831(2) 0.2281(2) 0.94090(11) 0.0494(5) Uani 1 1 d .
C11 C 0.5615(2) 0.0946(3) 0.90840(13) 0.0643(6) Uani 1 1 d .
H11 H 0.6036 0.0140 0.9321 0.077 Uiso 1 1 calc R
C12 C 0.4768(3) 0.0814(3) 0.84033(14) 0.0728(7) Uani 1 1 d .
H12 H 0.4619 -0.0091 0.8183 0.087 Uiso 1 1 calc R
C13 C 0.4137(2) 0.1986(3) 0.80404(14) 0.0678(7) Uani 1 1 d .
C14 C 0.4364(2) 0.3318(3) 0.83820(13) 0.0639(6) Uani 1 1 d .
H14 H 0.3942 0.4124 0.8144 0.077 Uiso 1 1 calc R
C15 C 0.5199(2) 0.3478(2) 0.90651(12) 0.0549(5) Uani 1 1 d .
H15 H 0.5335 0.4379 0.9292 0.066 Uiso 1 1 calc R
C16 C 0.3218(3) 0.1844(4) 0.72885(17) 0.1081(11) Uani 1 1 d .
H16A H 0.3746 0.1378 0.6900 0.162 Uiso 1 1 calc R
H16B H 0.2931 0.2781 0.7105 0.162 Uiso 1 1 calc R
H16C H 0.2393 0.1284 0.7382 0.162 Uiso 1 1 calc R
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
O3 S1 O2 120.15(10)
O3 S1 O1 103.60(11)
O2 S1 O1 109.06(9)
O3 S1 C10 109.05(9)
O2 S1 C10 109.99(11)
O1 S1 C10 103.59(8)
C1 O1 S1 118.65(13)
C2 C1 O1 116.31(17)
C2 C1 C4 127.33(19)
O1 C1 C4 116.31(17)
C1 C2 F1 118.48(18)
C1 C2 C3 129.6(2)
F1 C2 C3 111.82(19)
C2 C3 H3A 109.5
C2 C3 H3B 109.5
H3A C3 H3B 109.5
C2 C3 H3C 109.5
H3A C3 H3C 109.5
H3B C3 H3C 109.5
C5 C4 C9 118.8(2)
C5 C4 C1 121.05(19)
C9 C4 C1 120.1(2)
C6 C5 C4 120.4(2)
C6 C5 H5 119.8
C4 C5 H5 119.8
C7 C6 C5 120.4(3)
C7 C6 H6 119.8
C5 C6 H6 119.8
C8 C7 C6 119.7(2)
C8 C7 H7 120.2
C6 C7 H7 120.2
C7 C8 C9 120.6(3)
C7 C8 H8 119.7
C9 C8 H8 119.7
C8 C9 C4 120.1(2)
C8 C9 H9 120.0
C4 C9 H9 120.0
C11 C10 C15 120.7(2)
C11 C10 S1 120.59(17)
C15 C10 S1 118.67(17)
C10 C11 C12 119.2(2)
C10 C11 H11 120.4
C12 C11 H11 120.4
C13 C12 C11 121.5(2)
C13 C12 H12 119.2
C11 C12 H12 119.2
C12 C13 C14 118.2(2)
C12 C13 C16 121.6(3)
C14 C13 C16 120.2(3)
C15 C14 C13 121.4(2)
C15 C14 H14 119.3
C13 C14 H14 119.3
C14 C15 C10 118.9(2)
C14 C15 H15 120.5
C10 C15 H15 120.5
C13 C16 H16A 109.5
C13 C16 H16B 109.5
H16A C16 H16B 109.5
C13 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O3 1.4121(15)
S1 O2 1.4149(17)
S1 O1 1.5885(16)
S1 C10 1.745(2)
F1 C2 1.351(2)
O1 C1 1.421(2)
C1 C2 1.309(3)
C1 C4 1.470(3)
C2 C3 1.471(3)
C3 H3A 0.9600
C3 H3B 0.9600
C3 H3C 0.9600
C4 C5 1.378(3)
C4 C9 1.381(3)
C5 C6 1.375(3)
C5 H5 0.9300
C6 C7 1.364(4)
C6 H6 0.9300
C7 C8 1.361(4)
C7 H7 0.9300
C8 C9 1.378(3)
C8 H8 0.9300
C9 H9 0.9300
C10 C11 1.372(3)
C10 C15 1.378(3)
C11 C12 1.374(3)
C11 H11 0.9300
C12 C13 1.373(4)
C12 H12 0.9300
C13 C14 1.382(3)
C13 C16 1.509(3)
C14 C15 1.374(3)
C14 H14 0.9300
C15 H15 0.9300
C16 H16A 0.9600
C16 H16B 0.9600
C16 H16C 0.9600
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
O3 S1 O1 C1 156.90(13)
O2 S1 O1 C1 27.82(15)
C10 S1 O1 C1 -89.28(14)
S1 O1 C1 C2 -112.00(18)
S1 O1 C1 C4 70.37(19)
O1 C1 C2 F1 5.2(3)
C4 C1 C2 F1 -177.51(19)
O1 C1 C2 C3 -171.4(2)
C4 C1 C2 C3 5.9(4)
C2 C1 C4 C5 53.2(3)
O1 C1 C4 C5 -129.4(2)
C2 C1 C4 C9 -128.6(2)
O1 C1 C4 C9 48.7(3)
C9 C4 C5 C6 -0.4(3)
C1 C4 C5 C6 177.8(2)
C4 C5 C6 C7 0.0(4)
C5 C6 C7 C8 0.0(4)
C6 C7 C8 C9 0.5(4)
C7 C8 C9 C4 -0.9(4)
C5 C4 C9 C8 0.8(3)
C1 C4 C9 C8 -177.33(19)
O3 S1 C10 C11 -131.40(18)
O2 S1 C10 C11 2.3(2)
O1 S1 C10 C11 118.76(17)
O3 S1 C10 C15 47.9(2)
O2 S1 C10 C15 -178.36(16)
O1 S1 C10 C15 -61.91(17)
C15 C10 C11 C12 0.7(3)
S1 C10 C11 C12 -179.98(17)
C10 C11 C12 C13 0.1(4)
C11 C12 C13 C14 -0.5(4)
C11 C12 C13 C16 179.4(2)
C12 C13 C14 C15 0.1(3)
C16 C13 C14 C15 -179.8(2)
C13 C14 C15 C10 0.7(3)
C11 C10 C15 C14 -1.1(3)
S1 C10 C15 C14 179.57(15)
