#------------------------------------------------------------------------------
#$Date: 2015-07-09 01:09:00 +0300 (Thu, 09 Jul 2015) $
#$Revision: 141406 $
#$URL: svn://www.crystallography.net/cod/cif/1/52/01/1520117.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_1520117
loop_
_publ_author_name
'Matsuzaki, Kohei'
'Okuyama, Kenta'
'Tokunaga, Etsuko'
'Saito, Norimichi'
'Shiro, Motoo'
'Shibata, Norio'
_publ_section_title
;
 Synthesis of Diaryliodonium Salts Having Pentafluorosulfanylarenes and
 Their Application to Electrophilic Pentafluorosulfanylarylation of C-,
 O-, N-, and S-Nucleophiles.
;
_journal_issue                   12
_journal_name_full               'Organic letters'
_journal_page_first              3038
_journal_page_last               3041
_journal_paper_doi               10.1021/acs.orglett.5b01323
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C15 H15 F5 I S, C1 F3 O3 S, 0.5(C3 H6 O)'
_chemical_formula_sum            'C17.5 H18 F8 I O3.5 S2'
_chemical_formula_weight         627.34
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_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
_cell_angle_alpha                63.1630(10)
_cell_angle_beta                 87.5260(10)
_cell_angle_gamma                77.6000(10)
_cell_formula_units_Z            2
_cell_length_a                   8.9435(2)
_cell_length_b                   12.1892(3)
_cell_length_c                   12.2642(3)
_cell_measurement_reflns_used    11064
_cell_measurement_temperature    173
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      3.23
_cell_volume                     1162.92(5)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.1'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS2013 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.990
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_laue_measured_fraction_full 0.996
_diffrn_reflns_laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            5276
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.476
_diffrn_reflns_theta_min         3.226
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.640
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.791
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             616.00
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         1.11
_refine_diff_density_min         -0.70
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.194
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     294
_refine_ls_number_reflns         5276
_refine_ls_number_restraints     75
_refine_ls_R_factor_all          0.0292
_refine_ls_R_factor_gt           0.0275
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0592P)²+0.5814P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0879
_refine_ls_wR_factor_ref         0.0929
_reflns_number_gt                5017
_reflns_number_total             5276
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            ol5b01323_si_002.cif
_cod_data_source_block           20141118
_cod_depositor_comments          'Adding full bibliography for 1520117.cif.'
_cod_database_code               1520117
loop_
_symmetry_equiv_pos_site_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -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_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.79487(2) 0.37710(2) 0.44609(2) 0.03156(8) Uani 1 2 d . . .
S1 S 0.43241(9) 0.70878(7) -0.00682(6) 0.04014(16) Uani 1 2 d . . .
F1 F 0.3303(3) 0.6390(2) -0.04532(19) 0.0595(5) Uani 1 2 d . . .
F2 F 0.5813(3) 0.6295(2) -0.03283(18) 0.0593(6) Uani 1 2 d . . .
F3 F 0.5331(3) 0.7851(2) 0.02133(19) 0.0593(5) Uani 1 2 d . . .
F4 F 0.2822(3) 0.79499(19) 0.0080(2) 0.0589(5) Uani 1 2 d . . .
F5 F 0.4234(3) 0.8081(2) -0.14648(17) 0.0597(5) Uani 1 2 d . . .
C1 C 0.7688(3) 0.1897(2) 0.5128(2) 0.0280(5) Uani 1 2 d . . .
C2 C 0.7086(3) 0.1337(3) 0.6277(2) 0.0320(5) Uani 1 2 d . . .
C3 C 0.6793(3) 0.0147(3) 0.6632(3) 0.0381(6) Uani 1 2 d . . .
H3 H 0.63768 -0.02636 0.74011 0.0457 Uiso 1 2 calc R . .
C4 C 0.7093(3) -0.0455(3) 0.5889(3) 0.0389(6) Uani 1 2 d . . .
C5 C 0.7744(3) 0.0124(3) 0.4786(3) 0.0375(6) Uani 1 2 d . . .
H5 H 0.79842 -0.03043 0.42964 0.0450 Uiso 1 2 calc R . .
C6 C 0.8061(3) 0.1315(3) 0.4370(2) 0.0310(5) Uani 1 2 d . . .
C7 C 0.6756(4) 0.1936(3) 0.7125(3) 0.0426(6) Uani 1 2 d . . .
H7A H 0.76581 0.22259 0.72251 0.0511 Uiso 1 2 calc R . .
H7B H 0.65148 0.13172 0.79245 0.0511 Uiso 1 2 calc R . .
H7C H 0.58803 0.26559 0.67782 0.0511 Uiso 1 2 calc R . .
C8 C 0.6709(5) -0.1722(3) 0.6268(4) 0.0561(9) Uani 1 2 d . . .
H8A H 0.69122 -0.22353 0.71546 0.0673 Uiso 1 2 calc R . .
H8B H 0.73436 -0.21506 0.58428 0.0673 Uiso 1 2 calc R . .
H8C H 0.56233 -0.1601 0.60527 0.0673 Uiso 1 2 calc R . .
C9 C 0.8772(4) 0.1900(3) 0.3160(3) 0.0433(6) Uani 1 2 d . . .
H9A H 0.97233 0.21171 0.32842 0.0520 Uiso 1 2 calc R . .
H9B H 0.80554 0.26646 0.25922 0.0520 Uiso 1 2 calc R . .
H9C H 0.9001 0.12994 0.28179 0.0520 Uiso 1 2 calc R . .
C10 C 0.5839(3) 0.4556(2) 0.3405(2) 0.0307(5) Uani 1 2 d . . .
C11 C 0.5830(3) 0.5426(2) 0.2187(2) 0.0323(5) Uani 1 2 d . . .
H11 H 0.67436 0.56612 0.18219 0.0387 Uiso 1 2 calc R . .
C12 C 0.4419(3) 0.5938(2) 0.1526(2) 0.0324(5) Uani 1 2 d . . .
C13 C 0.3085(3) 0.5612(3) 0.2047(3) 0.0357(5) Uani 1 2 d . . .
H13 H 0.21362 0.59805 0.15738 0.0428 Uiso 1 2 calc R . .
C14 C 0.3140(3) 0.4739(3) 0.3270(3) 0.0366(5) Uani 1 2 d . . .
H14 H 0.22242 0.45129 0.36357 0.0439 Uiso 1 2 calc R . .
C15 C 0.4531(3) 0.4195(2) 0.3963(3) 0.0335(5) Uani 1 2 d . . .
H15 H 0.45798 0.359 0.47981 0.0402 Uiso 1 2 calc R . .
S2 S 1.13190(7) 0.29038(6) 0.66587(7) 0.03491(15) Uani 1 2 d U . .
O1 O 1.0845(3) 0.2619(3) 0.5726(3) 0.0582(6) Uani 1 2 d U . .
O2 O 1.2656(3) 0.3417(2) 0.6440(3) 0.0571(6) Uani 1 2 d U . .
O3 O 1.0081(4) 0.3549(4) 0.7067(4) 0.0914(11) Uani 1 2 d U . .
C16 C 1.1905(7) 0.1367(5) 0.7946(5) 0.0852(14) Uani 1 2 d U . .
F6 F 1.3152(5) 0.0708(3) 0.7635(4) 0.1262(14) Uani 1 2 d U . .
F7 F 1.2352(5) 0.1419(4) 0.8901(3) 0.1255(14) Uani 1 2 d U . .
F8 F 1.0861(6) 0.0726(4) 0.8198(4) 0.158(2) Uani 1 2 d U . .
O4 O 0.9261(15) 0.4847(10) 0.1288(8) 0.069(3) Uiso 0.25 2 d GUP A -1
C17 C 0.9591(11) 0.5506(8) 0.0243(8) 0.049(3) Uiso 0.25 2 d GUP A -1
C18 C 0.934(3) 0.6914(8) -0.0270(14) 0.059(4) Uiso 0.25 2 d GUP A -1
H18A H 0.96707 0.72679 -0.11085 0.0711 Uiso 0.25 2 calc RP A -1
H18B H 0.82476 0.72731 -0.02724 0.0711 Uiso 0.25 2 calc RP A -1
H18C H 0.99362 0.71181 0.02384 0.0711 Uiso 0.25 2 calc RP A -1
C19 C 1.027(2) 0.4943(13) -0.0584(11) 0.059(3) Uiso 0.25 2 d GUP A -1
H19A H 1.04472 0.56142 -0.13726 0.0711 Uiso 0.25 2 calc RP A -1
H19B H 1.12379 0.43457 -0.02045 0.0711 Uiso 0.25 2 calc RP A -1
H19C H 0.95493 0.45007 -0.07153 0.0711 Uiso 0.25 2 calc RP A -1
O4A O 1.005(2) 0.4484(14) 0.1401(10) 0.087(4) Uiso 0.25 2 d GUP B -2
C17A C 1.0189(18) 0.4395(12) 0.0440(10) 0.069(3) Uiso 0.25 2 d GUP B -2
C18A C 0.978(3) 0.5531(16) -0.0787(10) 0.082(4) Uiso 0.25 2 d GUP B -2
H18D H 0.99679 0.52696 -0.14366 0.0981 Uiso 0.25 2 calc RP B -2
H18E H 0.86933 0.59319 -0.08368 0.0981 Uiso 0.25 2 calc RP B -2
H18F H 1.04106 0.61315 -0.08853 0.0981 Uiso 0.25 2 calc RP B -2
C19A C 1.078(3) 0.3145(15) 0.0434(18) 0.072(5) Uiso 0.25 2 d GUP B -2
H19D H 1.08045 0.32681 -0.04128 0.0868 Uiso 0.25 2 calc RP B -2
H19E H 1.1813 0.27762 0.08311 0.0868 Uiso 0.25 2 calc RP B -2
H19F H 1.00958 0.25765 0.08797 0.0868 Uiso 0.25 2 calc RP B -2
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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
F F 0.0171 0.0103
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
I I -0.4742 1.8119
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.1246 0.1234
;
International Tables for Crystallography
(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_publ_flag
C1 I1 C10 93.76(10) yes
F1 S1 F2 89.62(15) yes
F1 S1 F3 175.86(10) yes
F1 S1 F4 89.70(14) yes
F1 S1 F5 87.75(13) yes
F1 S1 C12 91.60(14) yes
F2 S1 F3 90.18(14) yes
F2 S1 F4 175.52(11) yes
F2 S1 F5 87.54(11) yes
F2 S1 C12 92.31(11) yes
F3 S1 F4 90.18(14) yes
F3 S1 F5 88.11(13) yes
F3 S1 C12 92.54(14) yes
F4 S1 F5 88.00(11) yes
F4 S1 C12 92.14(12) yes
F5 S1 C12 179.34(17) yes
I1 C1 C2 118.1(2) yes
I1 C1 C6 117.73(17) yes
C2 C1 C6 124.1(3) yes
C1 C2 C3 116.3(3) yes
C1 C2 C7 124.2(3) yes
C3 C2 C7 119.5(3) yes
C2 C3 C4 121.8(3) yes
C3 C4 C5 119.2(3) yes
C3 C4 C8 121.0(3) yes
C5 C4 C8 119.8(4) yes
C4 C5 C6 122.1(4) yes
C1 C6 C5 116.4(3) yes
C1 C6 C9 123.8(3) yes
C5 C6 C9 119.8(3) yes
I1 C10 C11 118.3(2) yes
I1 C10 C15 118.61(17) yes
C11 C10 C15 123.1(2) yes
C10 C11 C12 116.7(3) yes
S1 C12 C11 119.0(2) yes
S1 C12 C13 118.8(2) yes
C11 C12 C13 122.2(2) yes
C12 C13 C14 119.4(3) yes
C13 C14 C15 120.3(3) yes
C10 C15 C14 118.3(2) yes
O1 S2 O2 115.91(18) yes
O1 S2 O3 113.1(2) yes
O1 S2 C16 102.9(3) yes
O2 S2 O3 114.1(2) yes
O2 S2 C16 104.2(2) yes
O3 S2 C16 104.8(2) yes
S2 C16 F6 108.0(4) yes
S2 C16 F7 112.7(4) yes
S2 C16 F8 112.2(4) yes
F6 C16 F7 106.1(5) yes
F6 C16 F8 106.6(5) yes
F7 C16 F8 110.8(5) yes
O4 C17 C18 121.6(12) yes
O4 C17 C19 121.6(10) yes
C18 C17 C19 116.7(10) yes
O4A C17A C18A 121.6(15) yes
O4A C17A C19A 121.6(12) yes
C18A C17A C19A 116.7(14) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
I1 C1 2.114(3) yes
I1 C10 2.114(3) yes
S1 F1 1.586(3) yes
S1 F2 1.581(2) yes
S1 F3 1.572(3) yes
S1 F4 1.577(2) yes
S1 F5 1.5823(18) yes
S1 C12 1.812(2) yes
C1 C2 1.402(4) yes
C1 C6 1.394(5) yes
C2 C3 1.394(5) yes
C2 C7 1.507(5) yes
C3 C4 1.392(6) yes
C4 C5 1.384(4) yes
C4 C8 1.511(5) yes
C5 C6 1.394(4) yes
C6 C9 1.507(4) yes
C10 C11 1.387(3) yes
C10 C15 1.383(4) yes
C11 C12 1.391(4) yes
C12 C13 1.377(4) yes
C13 C14 1.388(4) yes
C14 C15 1.392(4) yes
S2 O1 1.440(4) yes
S2 O2 1.426(3) yes
S2 O3 1.425(4) yes
S2 C16 1.804(4) yes
C16 F6 1.374(7) yes
C16 F7 1.286(8) yes
C16 F8 1.285(8) yes
O4 C17 1.230(12) yes
C17 C18 1.505(13) yes
C17 C19 1.50(2) yes
O4A C17A 1.23(2) yes
C17A C18A 1.505(15) yes
C17A C19A 1.50(3) yes
