#------------------------------------------------------------------------------
#$Date: 2016-03-21 17:03:29 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178766 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/20/4102007.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_4102007
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            'C21 H18 F N O4 S2'
_chemical_formula_weight         431.48
_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                105.759(2)
_cell_angle_beta                 94.136(2)
_cell_angle_gamma                102.117(2)
_cell_formula_units_Z            2
_cell_length_a                   8.3529(10)
_cell_length_b                   9.3193(11)
_cell_length_c                   13.6920(17)
_cell_measurement_reflns_used    2309
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      53.326
_cell_measurement_theta_min      4.677
_cell_volume                     993.4(2)
_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 0.982
_diffrn_measured_fraction_theta_max 0.982
_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  0.0690
_diffrn_reflns_av_sigmaI/netI    0.0619
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5487
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.34
_exptl_absorpt_coefficient_mu    0.306
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.27276
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.369
_exptl_crystal_size_mid          0.275
_exptl_crystal_size_min          0.231
_refine_diff_density_max         0.368
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.975
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3841
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.975
_refine_ls_R_factor_all          0.0558
_refine_ls_R_factor_gt           0.0456
_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)+(0.0679P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1153
_refine_ls_wR_factor_ref         0.1211
_reflns_number_gt                3081
_reflns_number_total             3841
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja909716k_si_008.cif
_cod_data_source_block           cd29548
_cod_database_code               4102007
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
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.75703(6) 0.37438(7) 0.63946(4) 0.04642(18) Uani 1 1 d . . .
S2 S 0.73663(7) 0.15741(6) 0.76229(4) 0.04790(18) Uani 1 1 d . . .
F1 F 1.14121(16) 0.53384(18) 0.92508(10) 0.0689(4) Uani 1 1 d . . .
N1 N 0.7811(2) 0.33675(19) 0.75231(12) 0.0421(4) Uani 1 1 d . . .
O1 O 0.88787(18) 0.5031(2) 0.64584(12) 0.0601(4) Uani 1 1 d . . .
O2 O 0.7423(2) 0.2343(2) 0.56183(12) 0.0708(5) Uani 1 1 d . . .
O3 O 0.59767(19) 0.06989(18) 0.68915(14) 0.0692(5) Uani 1 1 d . . .
O4 O 0.7280(2) 0.17587(18) 0.86794(13) 0.0618(5) Uani 1 1 d . . .
C1 C 0.8633(2) 0.4646(2) 0.84592(14) 0.0406(5) Uani 1 1 d . . .
H1 H 0.8677 0.4196 0.9027 0.049 Uiso 1 1 calc R . .
C2 C 1.0409(3) 0.5493(3) 0.84290(16) 0.0476(5) Uani 1 1 d . . .
H2 H 1.0781 0.5061 0.7773 0.057 Uiso 1 1 calc R . .
C3 C 1.0435(3) 0.7174(3) 0.8600(2) 0.0617(6) Uani 1 1 d . . .
H3A H 1.1276 0.7817 0.9164 0.074 Uiso 1 1 calc R . .
H3B H 1.0654 0.7475 0.7989 0.074 Uiso 1 1 calc R . .
C4 C 0.8729(3) 0.7311(2) 0.88505(16) 0.0485(5) Uani 1 1 d . . .
C5 C 0.7715(3) 0.5896(2) 0.87590(14) 0.0409(5) Uani 1 1 d . . .
C6 C 0.6105(3) 0.5743(3) 0.89710(17) 0.0516(5) Uani 1 1 d . . .
H6 H 0.5434 0.4785 0.8917 0.062 Uiso 1 1 calc R . .
C7 C 0.5522(3) 0.7059(3) 0.9267(2) 0.0666(7) Uani 1 1 d . . .
H7 H 0.4445 0.6989 0.9416 0.080 Uiso 1 1 calc R . .
C8 C 0.6527(4) 0.8476(3) 0.9341(2) 0.0715(8) Uani 1 1 d . . .
H8 H 0.6115 0.9350 0.9531 0.086 Uiso 1 1 calc R . .
C9 C 0.8125(3) 0.8607(3) 0.9138(2) 0.0643(7) Uani 1 1 d . . .
H9 H 0.8797 0.9565 0.9194 0.077 Uiso 1 1 calc R . .
C10 C 0.5710(2) 0.4331(3) 0.63391(14) 0.0430(5) Uani 1 1 d . . .
C11 C 0.4220(3) 0.3276(3) 0.61743(18) 0.0591(6) Uani 1 1 d . . .
H11 H 0.4178 0.2247 0.6104 0.071 Uiso 1 1 calc R . .
C12 C 0.2781(3) 0.3787(4) 0.6116(2) 0.0742(8) Uani 1 1 d . . .
H12 H 0.1759 0.3103 0.6026 0.089 Uiso 1 1 calc R . .
C13 C 0.2860(4) 0.5299(4) 0.6191(2) 0.0717(8) Uani 1 1 d . . .
H13 H 0.1888 0.5624 0.6128 0.086 Uiso 1 1 calc R . .
C14 C 0.4339(3) 0.6327(3) 0.6354(2) 0.0667(7) Uani 1 1 d . . .
H14 H 0.4378 0.7352 0.6413 0.080 Uiso 1 1 calc R . .
C15 C 0.5789(3) 0.5848(3) 0.64332(17) 0.0550(6) Uani 1 1 d . . .
H15 H 0.6807 0.6547 0.6549 0.066 Uiso 1 1 calc R . .
C16 C 0.9116(3) 0.0872(2) 0.73072(17) 0.0453(5) Uani 1 1 d . . .
C17 C 1.0560(3) 0.1432(3) 0.7983(2) 0.0579(6) Uani 1 1 d . . .
H17 H 1.0614 0.2168 0.8606 0.070 Uiso 1 1 calc R . .
C18 C 1.1934(3) 0.0877(3) 0.7713(2) 0.0700(7) Uani 1 1 d . . .
H18 H 1.2921 0.1247 0.8159 0.084 Uiso 1 1 calc R . .
C19 C 1.1843(4) -0.0212(3) 0.6797(3) 0.0731(8) Uani 1 1 d . . .
H19 H 1.2769 -0.0576 0.6622 0.088 Uiso 1 1 calc R . .
C20 C 1.0414(4) -0.0760(3) 0.6144(2) 0.0774(8) Uani 1 1 d . . .
H20 H 1.0364 -0.1507 0.5527 0.093 Uiso 1 1 calc R . .
C21 C 0.9025(3) -0.0222(3) 0.63847(19) 0.0628(7) Uani 1 1 d . . .
H21 H 0.8047 -0.0594 0.5931 0.075 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 119.78(10) . . ?
O2 S1 N1 106.75(10) . . ?
O1 S1 N1 105.87(9) . . ?
O2 S1 C10 109.82(10) . . ?
O1 S1 C10 107.62(10) . . ?
N1 S1 C10 106.16(9) . . ?
O3 S2 O4 119.61(11) . . ?
O3 S2 N1 108.30(10) . . ?
O4 S2 N1 104.96(9) . . ?
O3 S2 C16 109.79(10) . . ?
O4 S2 C16 108.29(10) . . ?
N1 S2 C16 104.83(9) . . ?
C1 N1 S2 117.83(13) . . ?
C1 N1 S1 119.24(13) . . ?
S2 N1 S1 122.54(10) . . ?
N1 C1 C5 114.17(16) . . ?
N1 C1 C2 116.51(15) . . ?
C5 C1 C2 104.80(16) . . ?
N1 C1 H1 106.9 . . ?
C5 C1 H1 106.9 . . ?
C2 C1 H1 106.9 . . ?
F1 C2 C3 109.23(19) . . ?
F1 C2 C1 106.82(16) . . ?
C3 C2 C1 107.76(16) . . ?
F1 C2 H2 111.0 . . ?
C3 C2 H2 111.0 . . ?
C1 C2 H2 111.0 . . ?
C4 C3 C2 104.86(18) . . ?
C4 C3 H3A 110.8 . . ?
C2 C3 H3A 110.8 . . ?
C4 C3 H3B 110.8 . . ?
C2 C3 H3B 110.8 . . ?
H3A C3 H3B 108.9 . . ?
C9 C4 C5 119.6(2) . . ?
C9 C4 C3 129.0(2) . . ?
C5 C4 C3 111.38(19) . . ?
C4 C5 C6 121.6(2) . . ?
C4 C5 C1 110.79(18) . . ?
C6 C5 C1 127.58(19) . . ?
C5 C6 C7 118.0(2) . . ?
C5 C6 H6 121.0 . . ?
C7 C6 H6 121.0 . . ?
C8 C7 C6 120.5(2) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C9 C8 C7 120.6(2) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C8 C9 C4 119.6(2) . . ?
C8 C9 H9 120.2 . . ?
C4 C9 H9 120.2 . . ?
C15 C10 C11 121.5(2) . . ?
C15 C10 S1 118.28(17) . . ?
C11 C10 S1 120.23(18) . . ?
C10 C11 C12 118.2(2) . . ?
C10 C11 H11 120.9 . . ?
C12 C11 H11 120.9 . . ?
C13 C12 C11 120.3(3) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C14 C13 C12 120.8(2) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C13 C14 C15 119.9(3) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C10 C15 C14 119.3(2) . . ?
C10 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
C21 C16 C17 121.0(2) . . ?
C21 C16 S2 119.51(18) . . ?
C17 C16 S2 119.54(17) . . ?
C16 C17 C18 118.7(2) . . ?
C16 C17 H17 120.7 . . ?
C18 C17 H17 120.7 . . ?
C19 C18 C17 120.4(3) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C20 C19 C18 120.4(2) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C19 C20 C21 120.8(3) . . ?
C19 C20 H20 119.6 . . ?
C21 C20 H20 119.6 . . ?
C16 C21 C20 118.9(3) . . ?
C16 C21 H21 120.6 . . ?
C20 C21 H21 120.6 . . ?
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 1.4176(17) . ?
S1 O1 1.4209(17) . ?
S1 N1 1.6823(17) . ?
S1 C10 1.756(2) . ?
S2 O3 1.4166(17) . ?
S2 O4 1.4185(17) . ?
S2 N1 1.6795(18) . ?
S2 C16 1.758(2) . ?
F1 C2 1.411(2) . ?
N1 C1 1.495(3) . ?
C1 C5 1.508(3) . ?
C1 C2 1.536(3) . ?
C1 H1 0.9800 . ?
C2 C3 1.515(3) . ?
C2 H2 0.9800 . ?
C3 C4 1.512(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C9 1.376(3) . ?
C4 C5 1.378(3) . ?
C5 C6 1.383(3) . ?
C6 C7 1.384(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.381(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.371(4) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 C15 1.371(3) . ?
C10 C11 1.376(3) . ?
C11 C12 1.387(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.372(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.356(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.383(3) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C21 1.377(3) . ?
C16 C17 1.377(3) . ?
C17 C18 1.388(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.368(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.351(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.384(3) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C1 H1 F1 0.98 2.29 3.135(2) 144.0 2_767
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 151.99(14) . . . . ?
O4 S2 N1 C1 23.15(16) . . . . ?
C16 S2 N1 C1 -90.85(15) . . . . ?
O3 S2 N1 S1 -35.25(14) . . . . ?
O4 S2 N1 S1 -164.09(12) . . . . ?
C16 S2 N1 S1 81.91(14) . . . . ?
O2 S1 N1 C1 156.41(14) . . . . ?
O1 S1 N1 C1 27.75(16) . . . . ?
C10 S1 N1 C1 -86.46(16) . . . . ?
O2 S1 N1 S2 -16.25(14) . . . . ?
O1 S1 N1 S2 -144.92(12) . . . . ?
C10 S1 N1 S2 100.87(13) . . . . ?
S2 N1 C1 C5 -123.83(15) . . . . ?
S1 N1 C1 C5 63.16(19) . . . . ?
S2 N1 C1 C2 113.70(17) . . . . ?
S1 N1 C1 C2 -59.3(2) . . . . ?
N1 C1 C2 F1 -121.27(18) . . . . ?
C5 C1 C2 F1 111.50(18) . . . . ?
N1 C1 C2 C3 121.46(19) . . . . ?
C5 C1 C2 C3 -5.8(2) . . . . ?
F1 C2 C3 C4 -109.3(2) . . . . ?
C1 C2 C3 C4 6.4(2) . . . . ?
C2 C3 C4 C9 175.2(2) . . . . ?
C2 C3 C4 C5 -4.9(3) . . . . ?
C9 C4 C5 C6 -1.4(3) . . . . ?
C3 C4 C5 C6 178.7(2) . . . . ?
C9 C4 C5 C1 -178.8(2) . . . . ?
C3 C4 C5 C1 1.3(2) . . . . ?
N1 C1 C5 C4 -125.82(18) . . . . ?
C2 C1 C5 C4 2.8(2) . . . . ?
N1 C1 C5 C6 57.0(3) . . . . ?
C2 C1 C5 C6 -174.4(2) . . . . ?
C4 C5 C6 C7 0.9(3) . . . . ?
C1 C5 C6 C7 177.9(2) . . . . ?
C5 C6 C7 C8 0.2(4) . . . . ?
C6 C7 C8 C9 -0.9(4) . . . . ?
C7 C8 C9 C4 0.4(4) . . . . ?
C5 C4 C9 C8 0.7(4) . . . . ?
C3 C4 C9 C8 -179.4(3) . . . . ?
O2 S1 C10 C15 -136.29(18) . . . . ?
O1 S1 C10 C15 -4.34(19) . . . . ?
N1 S1 C10 C15 108.66(17) . . . . ?
O2 S1 C10 C11 41.8(2) . . . . ?
O1 S1 C10 C11 173.74(17) . . . . ?
N1 S1 C10 C11 -73.25(18) . . . . ?
C15 C10 C11 C12 -0.7(3) . . . . ?
S1 C10 C11 C12 -178.74(18) . . . . ?
C10 C11 C12 C13 2.0(4) . . . . ?
C11 C12 C13 C14 -2.1(4) . . . . ?
C12 C13 C14 C15 0.9(4) . . . . ?
C11 C10 C15 C14 -0.4(3) . . . . ?
S1 C10 C15 C14 177.62(17) . . . . ?
C13 C14 C15 C10 0.4(4) . . . . ?
O3 S2 C16 C21 8.4(2) . . . . ?
O4 S2 C16 C21 140.6(2) . . . . ?
N1 S2 C16 C21 -107.8(2) . . . . ?
O3 S2 C16 C17 -172.12(17) . . . . ?
O4 S2 C16 C17 -39.9(2) . . . . ?
N1 S2 C16 C17 71.75(19) . . . . ?
C21 C16 C17 C18 0.3(3) . . . . ?
S2 C16 C17 C18 -179.19(18) . . . . ?
C16 C17 C18 C19 -0.4(4) . . . . ?
C17 C18 C19 C20 -0.1(4) . . . . ?
C18 C19 C20 C21 0.6(4) . . . . ?
C17 C16 C21 C20 0.2(4) . . . . ?
S2 C16 C21 C20 179.7(2) . . . . ?
C19 C20 C21 C16 -0.7(4) . . . . ?
