#------------------------------------------------------------------------------
#$Date: 2016-03-21 18:45:11 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178822 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/76/4107637.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_4107637
loop_
_publ_author_name
'Robert Weiss'
'Matthias Bess'
'Stefan M. Huber'
'Frank W. Heinemann'
_publ_section_title
;
 Nucleophilic β-Oniovinylation: Concept, Mechanism, Scope, and
 Applications
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              4610
_journal_page_last               4617
_journal_paper_doi               10.1021/ja071316a
_journal_volume                  130
_journal_year                    2008
_chemical_formula_sum            'C21 H21 F3 N2 O8 S'
_chemical_formula_weight         518.46
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                94.562(1)
_cell_angle_beta                 98.250(1)
_cell_angle_gamma                112.007(1)
_cell_formula_units_Z            2
_cell_length_a                   8.7141(2)
_cell_length_b                   11.1733(2)
_cell_length_c                   13.1992(2)
_cell_measurement_reflns_used    5094
_cell_measurement_temperature    173(2)
_cell_volume                     1166.66(4)
_computing_cell_refinement       DENZO-SMN
_computing_data_collection       'Nonius Collect'
_computing_data_reduction        DENZO-SMN
_computing_molecular_graphics    'SHELXTL NT'
_computing_publication_material  'SHELXTL NT'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0132
_diffrn_reflns_av_sigmaI/netI    0.0234
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10147
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         2.35
_exptl_absorpt_coefficient_mu    0.213
_exptl_absorpt_correction_T_max  0.9587
_exptl_absorpt_correction_T_min  0.9488
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   Scalepack
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.841
_refine_diff_density_min         -0.850
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.982
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     320
_refine_ls_number_reflns         5337
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.982
_refine_ls_R_factor_all          0.0596
_refine_ls_R_factor_gt           0.0513
_refine_ls_shift/su_max          0.025
_refine_ls_shift/su_mean         0.036
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0781P)²+0.9977P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1364
_refine_ls_wR_factor_ref         0.1435
_reflns_number_gt                4523
_reflns_number_total             5337
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja071316a-file006.cif
_cod_data_source_block           matb12
_cod_database_code               4107637
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
O1 O 0.60903(18) -0.08480(15) 0.23932(11) 0.0368(3) Uani 1 1 d .
C1 C 0.5101(2) -0.03162(17) 0.23201(14) 0.0251(4) Uani 1 1 d .
C2 C 0.5015(2) 0.04898(17) 0.32755(13) 0.0227(3) Uani 1 1 d .
C3 C 0.3590(2) 0.02960(16) 0.36207(13) 0.0217(3) Uani 1 1 d .
O4 O 0.19726(15) 0.10054(12) 0.45986(9) 0.0252(3) Uani 1 1 d .
O4A O 0.47902(17) 0.19208(15) 0.50954(11) 0.0368(3) Uani 1 1 d .
C4 C 0.3532(2) 0.11609(17) 0.45299(13) 0.0235(3) Uani 1 1 d .
O5A O 0.75806(17) 0.12302(15) 0.45067(12) 0.0378(3) Uani 1 1 d .
O5 O 0.70509(18) 0.25995(14) 0.34865(12) 0.0377(3) Uani 1 1 d .
C5 C 0.6691(2) 0.14759(18) 0.38523(14) 0.0258(4) Uani 1 1 d .
C6 C 0.1816(3) 0.1851(2) 0.54308(16) 0.0361(5) Uani 1 1 d .
H6A H 0.0621 0.1660 0.5424 0.054 Uiso 1 1 calc R
H6B H 0.2392 0.2763 0.5338 0.054 Uiso 1 1 calc R
H6C H 0.2328 0.1701 0.6094 0.054 Uiso 1 1 calc R
C7 C 0.8612(3) 0.3638(3) 0.4017(2) 0.0595(7) Uani 1 1 d .
H7A H 0.8711 0.4456 0.3757 0.089 Uiso 1 1 calc R
H7B H 0.9566 0.3422 0.3892 0.089 Uiso 1 1 calc R
H7C H 0.8613 0.3738 0.4762 0.089 Uiso 1 1 calc R
N8 N 0.20612(17) -0.07740(13) 0.31268(11) 0.0205(3) Uani 1 1 d .
C8 C 0.1991(2) -0.20198(17) 0.30643(14) 0.0242(3) Uani 1 1 d .
H8A H 0.2924 -0.2171 0.3406 0.029 Uiso 1 1 calc R
C9 C 0.0626(2) -0.30474(17) 0.25285(15) 0.0272(4) Uani 1 1 d .
H9A H 0.0627 -0.3900 0.2486 0.033 Uiso 1 1 calc R
N10 N -0.21965(19) -0.38311(15) 0.15098(13) 0.0290(3) Uani 1 1 d .
C10 C -0.0810(2) -0.28557(17) 0.20287(13) 0.0226(3) Uani 1 1 d .
C11 C -0.0691(2) -0.15421(16) 0.21242(13) 0.0212(3) Uani 1 1 d .
H11A H -0.1615 -0.1360 0.1810 0.025 Uiso 1 1 calc R
C12 C 0.0713(2) -0.05525(16) 0.26531(13) 0.0212(3) Uani 1 1 d .
H12A H 0.0763 0.0315 0.2696 0.025 Uiso 1 1 calc R
C13 C -0.2297(3) -0.5155(2) 0.1264(2) 0.0522(7) Uani 1 1 d .
H13A H -0.1235 -0.5206 0.1575 0.078 Uiso 1 1 calc R
H13B H -0.2497 -0.5390 0.0512 0.078 Uiso 1 1 calc R
H13C H -0.3225 -0.5761 0.1542 0.078 Uiso 1 1 calc R
C14 C -0.3682(2) -0.36106(18) 0.10564(15) 0.0300(4) Uani 1 1 d .
H14A H -0.3817 -0.2937 0.1515 0.045 Uiso 1 1 calc R
H14B H -0.4684 -0.4423 0.0970 0.045 Uiso 1 1 calc R
H14C H -0.3543 -0.3323 0.0381 0.045 Uiso 1 1 calc R
C15 C 0.3958(2) -0.04122(18) 0.13434(13) 0.0245(4) Uani 1 1 d .
C16 C 0.3472(3) -0.1504(2) 0.05966(16) 0.0346(4) Uani 1 1 d .
H16A H 0.3901 -0.2158 0.0708 0.042 Uiso 1 1 calc R
C17 C 0.2362(3) -0.1635(2) -0.03086(17) 0.0402(5) Uani 1 1 d .
H17A H 0.2015 -0.2387 -0.0813 0.048 Uiso 1 1 calc R
C18 C 0.1761(3) -0.0672(2) -0.04784(15) 0.0334(4) Uani 1 1 d .
H18A H 0.0991 -0.0768 -0.1096 0.040 Uiso 1 1 calc R
C19 C 0.2276(2) 0.04309(19) 0.02473(15) 0.0299(4) Uani 1 1 d .
H19A H 0.1884 0.1101 0.0117 0.036 Uiso 1 1 calc R
C20 C 0.3362(2) 0.05611(18) 0.11646(14) 0.0260(4) Uani 1 1 d .
H20A H 0.3699 0.1311 0.1669 0.031 Uiso 1 1 calc R
S100 S 0.22332(6) 0.36166(4) 0.22131(4) 0.03109(14) Uani 1 1 d .
C100 C 0.3750(3) 0.4846(3) 0.32368(19) 0.0476(6) Uani 1 1 d .
F101 F 0.4253(3) 0.60197(16) 0.29321(15) 0.0852(7) Uani 1 1 d .
O101 O 0.1768(4) 0.24639(17) 0.26795(18) 0.0790(7) Uani 1 1 d .
F102 F 0.3087(3) 0.49629(19) 0.40584(13) 0.0861(7) Uani 1 1 d .
O102 O 0.0961(3) 0.4101(2) 0.2016(2) 0.0882(9) Uani 1 1 d .
F103 F 0.5089(3) 0.4635(3) 0.3504(3) 0.1498(15) Uani 1 1 d .
O103 O 0.3169(3) 0.3593(2) 0.14246(16) 0.0720(7) 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'
N N 0.0061 0.0033 '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
O1 C1 C15 123.51(16)
O1 C1 C2 118.79(16)
C15 C1 C2 117.69(14)
C3 C2 C5 121.92(16)
C3 C2 C1 123.11(15)
C5 C2 C1 114.86(14)
C2 C3 N8 119.95(15)
C2 C3 C4 121.68(15)
N8 C3 C4 118.37(14)
C4 O4 C6 115.32(14)
O4A C4 O4 125.83(16)
O4A C4 C3 122.14(16)
O4 C4 C3 112.00(14)
C5 O5 C7 114.84(17)
O5A C5 O5 126.14(17)
O5A C5 C2 123.47(17)
O5 C5 C2 110.28(15)
C12 N8 C8 119.40(14)
C12 N8 C3 120.59(14)
C8 N8 C3 119.84(14)
C9 C8 N8 121.83(16)
C8 C9 C10 120.39(16)
C10 N10 C13 123.16(16)
C10 N10 C14 121.57(15)
C13 N10 C14 115.00(15)
N10 C10 C11 121.14(15)
N10 C10 C9 122.97(16)
C11 C10 C9 115.89(15)
C12 C11 C10 121.18(15)
C11 C12 N8 121.30(15)
C20 C15 C16 119.81(17)
C20 C15 C1 121.25(16)
C16 C15 C1 118.94(16)
C17 C16 C15 120.01(18)
C18 C17 C16 119.96(19)
C17 C18 C19 120.30(18)
C18 C19 C20 120.17(18)
C19 C20 C15 119.70(17)
O102 S100 O103 117.33(18)
O102 S100 O101 114.64(18)
O103 S100 O101 113.06(14)
O102 S100 C100 102.13(12)
O103 S100 C100 103.86(12)
O101 S100 C100 103.35(14)
F103 C100 F102 109.5(3)
F103 C100 F101 106.1(3)
F102 C100 F101 105.4(2)
F103 C100 S100 112.9(2)
F102 C100 S100 111.78(18)
F101 C100 S100 110.75(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.214(2)
C1 C15 1.482(2)
C1 C2 1.518(2)
C2 C3 1.332(2)
C2 C5 1.506(2)
C3 N8 1.436(2)
C3 C4 1.498(2)
O4 C4 1.322(2)
O4 C6 1.446(2)
O4A C4 1.203(2)
O5A C5 1.195(2)
O5 C5 1.324(2)
O5 C7 1.450(3)
N8 C12 1.365(2)
N8 C8 1.366(2)
C8 C9 1.356(2)
C9 C10 1.427(2)
N10 C10 1.332(2)
N10 C13 1.456(3)
N10 C14 1.461(2)
C10 C11 1.426(2)
C11 C12 1.351(2)
C15 C20 1.392(2)
C15 C16 1.393(3)
C16 C17 1.385(3)
C17 C18 1.382(3)
C18 C19 1.383(3)
C19 C20 1.387(3)
S100 O102 1.4066(19)
S100 O103 1.4157(19)
S100 O101 1.4173(19)
S100 C100 1.814(2)
C100 F103 1.282(3)
C100 F102 1.319(3)
C100 F101 1.333(3)
