#------------------------------------------------------------------------------
#$Date: 2016-03-21 17:03:29 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178766 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/20/4102005.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_4102005
loop_
_publ_author_name
'Shuifa Qiu'
'Tao Xu'
'Juan Zhou'
'Yinlong Guo'
'Guosheng Liu'
_publ_section_title
;
 Palladium-Catalyzed Intermolecular Aminofluorination of Styrenes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2856
_journal_page_last               2857
_journal_paper_doi               10.1021/ja909716k
_journal_volume                  132
_journal_year                    2010
_chemical_formula_sum            'C20 H17 F2 N O4 S2'
_chemical_formula_weight         437.47
_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                 100.447(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.7686(12)
_cell_length_b                   7.8219(6)
_cell_length_c                   17.1905(14)
_cell_measurement_reflns_used    4448
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      54.600
_cell_measurement_theta_min      4.819
_cell_volume                     1952.9(3)
_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 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0662
_diffrn_reflns_av_sigmaI/netI    0.0481
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            10322
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         2.41
_exptl_absorpt_coefficient_mu    0.319
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.39995
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.488
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.403
_exptl_crystal_size_mid          0.316
_exptl_crystal_size_min          0.286
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       0.0194(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3826
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0425
_refine_ls_shift/su_max          0.064
_refine_ls_shift/su_mean         0.015
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0704P)²+0.0316P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1142
_refine_ls_wR_factor_ref         0.1184
_reflns_number_gt                3230
_reflns_number_total             3826
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja909716k_si_006.cif
_cod_data_source_block           cd29518
_cod_database_code               4102005
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
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.34127(3) 0.21233(6) 0.35688(3) 0.04469(17) Uani 1 1 d . . .
S2 S 0.25602(4) -0.12618(6) 0.35054(3) 0.04568(17) Uani 1 1 d . . .
F1 F 0.17432(11) 0.1687(2) 0.48408(7) 0.0802(5) Uani 1 1 d . . .
F2 F 0.05549(9) 0.30141(19) 0.41869(8) 0.0676(4) Uani 1 1 d . . .
N1 N 0.24710(10) 0.08828(19) 0.35217(8) 0.0396(4) Uani 1 1 d . . .
O1 O 0.30843(10) 0.37984(17) 0.36805(9) 0.0559(4) Uani 1 1 d . . .
O2 O 0.41186(10) 0.1395(2) 0.41391(9) 0.0619(4) Uani 1 1 d . . .
O3 O 0.33909(12) -0.16095(19) 0.32367(10) 0.0659(5) Uani 1 1 d . . .
O4 O 0.17094(11) -0.18487(17) 0.30731(9) 0.0632(4) Uani 1 1 d . . .
C1 C 0.15336(12) 0.1643(2) 0.34644(10) 0.0381(4) Uani 1 1 d . . .
H1 H 0.1116 0.0671 0.3469 0.046 Uiso 1 1 calc R . .
C2 C 0.14621(14) 0.2677(3) 0.41984(11) 0.0488(5) Uani 1 1 d . . .
H2 H 0.1823 0.3733 0.4222 0.059 Uiso 1 1 calc R . .
C3 C 0.12032(12) 0.2545(2) 0.26863(10) 0.0371(4) Uani 1 1 d . . .
C4 C 0.09629(13) 0.1563(2) 0.20089(11) 0.0463(5) Uani 1 1 d . . .
H4 H 0.0989 0.0377 0.2044 0.056 Uiso 1 1 calc R . .
C5 C 0.06865(16) 0.2332(3) 0.12854(12) 0.0560(5) Uani 1 1 d . . .
H5 H 0.0538 0.1665 0.0832 0.067 Uiso 1 1 calc R . .
C6 C 0.06294(15) 0.4083(3) 0.12301(12) 0.0564(5) Uani 1 1 d . . .
H6 H 0.0448 0.4602 0.0740 0.068 Uiso 1 1 calc R . .
C7 C 0.08401(14) 0.5055(3) 0.18972(12) 0.0538(5) Uani 1 1 d . . .
H7 H 0.0789 0.6239 0.1861 0.065 Uiso 1 1 calc R . .
C8 C 0.11269(13) 0.4301(2) 0.26217(11) 0.0455(4) Uani 1 1 d . . .
H8 H 0.1271 0.4978 0.3072 0.055 Uiso 1 1 calc R . .
C9 C 0.37456(13) 0.2051(3) 0.26401(11) 0.0460(5) Uani 1 1 d . . .
C10 C 0.45016(15) 0.1091(3) 0.25374(14) 0.0571(5) Uani 1 1 d . . .
H10 H 0.4811 0.0423 0.2949 0.069 Uiso 1 1 calc R . .
C11 C 0.47906(17) 0.1136(3) 0.18210(16) 0.0688(7) Uani 1 1 d . . .
H11 H 0.5309 0.0524 0.1750 0.083 Uiso 1 1 calc R . .
C12 C 0.43146(18) 0.2081(4) 0.12126(15) 0.0703(7) Uani 1 1 d . . .
H12 H 0.4501 0.2075 0.0724 0.084 Uiso 1 1 calc R . .
C13 C 0.35708(18) 0.3031(4) 0.13113(15) 0.0720(7) Uani 1 1 d . . .
H13 H 0.3259 0.3678 0.0893 0.086 Uiso 1 1 calc R . .
C14 C 0.32755(15) 0.3039(3) 0.20341(13) 0.0580(6) Uani 1 1 d . . .
H14 H 0.2773 0.3694 0.2108 0.070 Uiso 1 1 calc R . .
C15 C 0.26431(14) -0.1962(2) 0.44845(12) 0.0448(4) Uani 1 1 d . . .
C16 C 0.18527(17) -0.2476(3) 0.47396(15) 0.0609(6) Uani 1 1 d . . .
H16 H 0.1283 -0.2427 0.4404 0.073 Uiso 1 1 calc R . .
C17 C 0.1928(2) -0.3065(3) 0.55032(18) 0.0811(8) Uani 1 1 d . . .
H17 H 0.1404 -0.3422 0.5686 0.097 Uiso 1 1 calc R . .
C18 C 0.2765(3) -0.3133(4) 0.59956(16) 0.0854(9) Uani 1 1 d . . .
H18 H 0.2807 -0.3526 0.6511 0.102 Uiso 1 1 calc R . .
C19 C 0.3537(2) -0.2627(4) 0.57331(17) 0.0864(9) Uani 1 1 d . . .
H19 H 0.4104 -0.2683 0.6071 0.104 Uiso 1 1 calc R . .
C20 C 0.34908(17) -0.2035(3) 0.49743(14) 0.0642(6) Uani 1 1 d . . .
H20 H 0.4020 -0.1691 0.4796 0.077 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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O1 120.27(9) . . ?
O2 S1 N1 107.41(8) . . ?
O1 S1 N1 103.78(8) . . ?
O2 S1 C9 108.94(10) . . ?
O1 S1 C9 108.13(9) . . ?
N1 S1 C9 107.61(8) . . ?
O3 S2 O4 120.43(10) . . ?
O3 S2 N1 105.80(8) . . ?
O4 S2 N1 105.50(8) . . ?
O3 S2 C15 109.88(9) . . ?
O4 S2 C15 107.68(9) . . ?
N1 S2 C15 106.70(8) . . ?
C1 N1 S2 118.05(11) . . ?
C1 N1 S1 121.38(11) . . ?
S2 N1 S1 120.53(9) . . ?
N1 C1 C3 112.99(14) . . ?
N1 C1 C2 111.14(15) . . ?
C3 C1 C2 115.27(15) . . ?
N1 C1 H1 105.5 . . ?
C3 C1 H1 105.5 . . ?
C2 C1 H1 105.5 . . ?
F1 C2 F2 106.18(16) . . ?
F1 C2 C1 108.47(16) . . ?
F2 C2 C1 107.91(16) . . ?
F1 C2 H2 111.4 . . ?
F2 C2 H2 111.4 . . ?
C1 C2 H2 111.4 . . ?
C8 C3 C4 118.61(17) . . ?
C8 C3 C1 122.90(15) . . ?
C4 C3 C1 118.49(16) . . ?
C5 C4 C3 120.42(18) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C6 C5 C4 120.18(19) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C7 C6 C5 119.71(19) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C6 C7 C8 120.59(19) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C7 C8 C3 120.46(18) . . ?
C7 C8 H8 119.8 . . ?
C3 C8 H8 119.8 . . ?
C10 C9 C14 121.01(19) . . ?
C10 C9 S1 119.96(16) . . ?
C14 C9 S1 118.92(16) . . ?
C11 C10 C9 119.3(2) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
C12 C11 C10 119.9(2) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C13 C12 C11 121.0(2) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C12 C13 C14 120.3(2) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.8 . . ?
C9 C14 C13 118.5(2) . . ?
C9 C14 H14 120.8 . . ?
C13 C14 H14 120.8 . . ?
C16 C15 C20 121.4(2) . . ?
C16 C15 S2 118.72(17) . . ?
C20 C15 S2 119.82(16) . . ?
C15 C16 C17 118.3(3) . . ?
C15 C16 H16 120.9 . . ?
C17 C16 H16 120.9 . . ?
C18 C17 C16 120.8(3) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C19 C18 C17 120.1(2) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C18 C19 C20 120.9(3) . . ?
C18 C19 H19 119.6 . . ?
C20 C19 H19 119.6 . . ?
C19 C20 C15 118.5(2) . . ?
C19 C20 H20 120.7 . . ?
C15 C20 H20 120.7 . . ?
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 O2 1.4151(15) . ?
S1 O1 1.4221(14) . ?
S1 N1 1.6857(15) . ?
S1 C9 1.7546(19) . ?
S2 O3 1.4135(15) . ?
S2 O4 1.4154(16) . ?
S2 N1 1.6833(15) . ?
S2 C15 1.753(2) . ?
F1 C2 1.351(2) . ?
F2 C2 1.362(2) . ?
N1 C1 1.493(2) . ?
C1 C3 1.512(2) . ?
C1 C2 1.518(2) . ?
C1 H1 0.9800 . ?
C2 H2 0.9800 . ?
C3 C8 1.381(3) . ?
C3 C4 1.386(2) . ?
C4 C5 1.375(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.375(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.364(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.374(3) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 C10 1.383(3) . ?
C9 C14 1.379(3) . ?
C10 C11 1.375(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.367(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.362(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.389(3) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C16 1.379(3) . ?
C15 C20 1.377(3) . ?
C16 C17 1.376(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.367(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.358(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.374(3) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
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
O3 S2 N1 C1 156.04(13) . . . . ?
O4 S2 N1 C1 27.38(14) . . . . ?
C15 S2 N1 C1 -86.96(14) . . . . ?
O3 S2 N1 S1 -21.83(13) . . . . ?
O4 S2 N1 S1 -150.49(11) . . . . ?
C15 S2 N1 S1 95.17(11) . . . . ?
O2 S1 N1 C1 138.28(13) . . . . ?
O1 S1 N1 C1 9.90(15) . . . . ?
C9 S1 N1 C1 -104.56(14) . . . . ?
O2 S1 N1 S2 -43.91(12) . . . . ?
O1 S1 N1 S2 -172.29(10) . . . . ?
C9 S1 N1 S2 73.25(12) . . . . ?
S2 N1 C1 C3 -110.15(14) . . . . ?
S1 N1 C1 C3 67.71(17) . . . . ?
S2 N1 C1 C2 118.46(14) . . . . ?
S1 N1 C1 C2 -63.69(18) . . . . ?
N1 C1 C2 F1 -52.4(2) . . . . ?
C3 C1 C2 F1 177.43(16) . . . . ?
N1 C1 C2 F2 -166.98(14) . . . . ?
C3 C1 C2 F2 62.8(2) . . . . ?
N1 C1 C3 C8 -108.91(18) . . . . ?
C2 C1 C3 C8 20.4(2) . . . . ?
N1 C1 C3 C4 71.4(2) . . . . ?
C2 C1 C3 C4 -159.33(17) . . . . ?
C8 C3 C4 C5 2.3(3) . . . . ?
C1 C3 C4 C5 -177.97(17) . . . . ?
C3 C4 C5 C6 -1.2(3) . . . . ?
C4 C5 C6 C7 -0.6(3) . . . . ?
C5 C6 C7 C8 1.3(3) . . . . ?
C6 C7 C8 C3 -0.2(3) . . . . ?
C4 C3 C8 C7 -1.6(3) . . . . ?
C1 C3 C8 C7 178.70(17) . . . . ?
O2 S1 C9 C10 11.55(19) . . . . ?
O1 S1 C9 C10 143.86(16) . . . . ?
N1 S1 C9 C10 -104.61(17) . . . . ?
O2 S1 C9 C14 -164.77(16) . . . . ?
O1 S1 C9 C14 -32.46(19) . . . . ?
N1 S1 C9 C14 79.07(18) . . . . ?
C14 C9 C10 C11 0.5(3) . . . . ?
S1 C9 C10 C11 -175.75(17) . . . . ?
C9 C10 C11 C12 -2.0(3) . . . . ?
C10 C11 C12 C13 2.2(4) . . . . ?
C11 C12 C13 C14 -0.8(4) . . . . ?
C10 C9 C14 C13 0.9(3) . . . . ?
S1 C9 C14 C13 177.15(18) . . . . ?
C12 C13 C14 C9 -0.7(4) . . . . ?
O3 S2 C15 C16 -150.66(17) . . . . ?
O4 S2 C15 C16 -17.78(19) . . . . ?
N1 S2 C15 C16 95.08(17) . . . . ?
O3 S2 C15 C20 27.5(2) . . . . ?
O4 S2 C15 C20 160.35(17) . . . . ?
N1 S2 C15 C20 -86.79(18) . . . . ?
C20 C15 C16 C17 0.3(3) . . . . ?
S2 C15 C16 C17 178.35(18) . . . . ?
C15 C16 C17 C18 0.2(4) . . . . ?
C16 C17 C18 C19 -0.5(4) . . . . ?
C17 C18 C19 C20 0.3(5) . . . . ?
C18 C19 C20 C15 0.1(4) . . . . ?
C16 C15 C20 C19 -0.4(4) . . . . ?
S2 C15 C20 C19 -178.5(2) . . . . ?
