#------------------------------------------------------------------------------
#$Date: 2025-08-21 00:40:30 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301839 $
#$URL: svn://www.crystallography.net/cod/cif/4/33/12/4331228.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_4331228
loop_
_publ_author_name
'Thomas P. Pell'
'Shannon A. Couchman'
'Sara Ibrahim'
'David J. D. Wilson'
'Brian J. Smith'
'Peter J. Barnard'
'Jason L. Dutton'
_publ_section_title
;
 Diverse Reactions of PhI(OTf)2 with Common 2-Electron Ligands: Complex
 Formation, Oxidation, and Oxidative Coupling
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              13034
_journal_page_last               13040
_journal_paper_doi               10.1021/ic302176f
_journal_volume                  51
_journal_year                    2012
_chemical_formula_sum            'C22 H25 F6 I N4 O6 S2'
_chemical_formula_weight         746.48
_space_group_IT_number           62
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   21.866(4)
_cell_length_b                   9.752(2)
_cell_length_c                   13.102(3)
_cell_measurement_reflns_used    6500
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.1361
_cell_measurement_theta_min      2.7599
_cell_volume                     2793.8(10)
_computing_cell_refinement       'CrysAlisPro, Agilent Technologies'
_computing_data_collection       'CrysAlisPro, Agilent Technologies'
_computing_data_reduction        'CrysAlisPro, Agilent Technologies'
_computing_molecular_graphics    SHELXP
_computing_publication_material  SHELXP
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω 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  0.0650
_diffrn_reflns_av_sigmaI/netI    0.0285
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            27604
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         2.77
_exptl_absorpt_coefficient_mu    1.381
_exptl_absorpt_correction_T_max  0.8518
_exptl_absorpt_correction_T_min  0.5452
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, Agilent Technologies'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.775
_exptl_crystal_description       plate
_exptl_crystal_F_000             1488
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_refine_diff_density_max         2.031
_refine_diff_density_min         -0.995
_refine_diff_density_rms         0.133
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.355
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         2713
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.355
_refine_ls_R_factor_all          0.0681
_refine_ls_R_factor_gt           0.0584
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0001P)²+28.6932P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1345
_refine_ls_wR_factor_ref         0.1387
_reflns_number_gt                2338
_reflns_number_total             2713
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic302176f_si_002_2.cif
_cod_data_source_block           8_NMe2
_cod_database_code               4331228
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, 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
I1 I 0.36713(3) 0.2500 0.07491(5) 0.0266(2) Uani 1 2 d S
N1 N 0.4667(4) 0.2500 0.0889(6) 0.0249(18) Uani 1 2 d S
N2 N 0.2659(4) 0.2500 0.0830(7) 0.0257(18) Uani 1 2 d S
N3 N 0.0765(4) 0.2500 0.1047(7) 0.033(2) Uani 1 2 d S
N4 N 0.6548(4) 0.2500 0.1277(8) 0.038(2) Uani 1 2 d S
C11 C 0.2345(3) 0.1314(7) 0.0898(5) 0.0264(16) Uani 1 1 d .
H5A H 0.2566 0.0475 0.0891 0.032 Uiso 1 1 calc R
C1 C 0.3663(4) 0.2500 0.2355(7) 0.026(2) Uani 1 2 d S
C21 C 0.4979(3) 0.1310(8) 0.0958(5) 0.0293(17) Uani 1 1 d .
H11A H 0.4758 0.0472 0.0927 0.035 Uiso 1 1 calc R
C2 C 0.3661(3) 0.3746(8) 0.2853(6) 0.0371(18) Uani 1 1 d .
H10A H 0.3668 0.4587 0.2488 0.045 Uiso 1 1 calc R
C22 C 0.5596(3) 0.1260(8) 0.1070(6) 0.0316(17) Uani 1 1 d .
H10B H 0.5799 0.0400 0.1105 0.038 Uiso 1 1 calc R
C12 C 0.1722(3) 0.1269(8) 0.0978(5) 0.0287(16) Uani 1 1 d .
H18A H 0.1520 0.0409 0.1017 0.034 Uiso 1 1 calc R
C23 C 0.5938(5) 0.2500 0.1134(8) 0.032(2) Uani 1 2 d S
C13 C 0.1377(5) 0.2500 0.1003(7) 0.026(2) Uani 1 2 d S
C3 C 0.3647(4) 0.3718(11) 0.3921(6) 0.050(2) Uani 1 1 d .
H20O H 0.3642 0.4556 0.4290 0.060 Uiso 1 1 calc R
C24 C 0.6893(4) 0.1213(10) 0.1315(7) 0.049(2) Uani 1 1 d .
H20C H 0.6740 0.0646 0.1878 0.073 Uiso 1 1 calc R
H20D H 0.7327 0.1413 0.1424 0.073 Uiso 1 1 calc R
H20E H 0.6842 0.0719 0.0669 0.073 Uiso 1 1 calc R
C14 C 0.0411(4) 0.1232(9) 0.1026(8) 0.050(2) Uani 1 1 d .
H20F H 0.0428 0.0835 0.0339 0.075 Uiso 1 1 calc R
H20G H -0.0015 0.1428 0.1205 0.075 Uiso 1 1 calc R
H20H H 0.0583 0.0581 0.1518 0.075 Uiso 1 1 calc R
C4 C 0.3642(5) 0.2500 0.4441(8) 0.050(4) Uani 1 2 d S
H20B H 0.3634 0.2500 0.5166 0.060 Uiso 1 2 calc SR
S1 S 0.08822(12) 0.7500 0.2621(2) 0.0340(6) Uani 1 2 d S
F1 F 0.0006(5) 0.7500 0.1294(8) 0.109(4) Uani 1 2 d S
F2 F -0.0210(2) 0.6408(6) 0.2613(7) 0.095(3) Uani 1 1 d .
O1 O 0.1108(3) 0.6270(6) 0.2191(6) 0.068(2) Uani 1 1 d .
O2 O 0.0867(5) 0.7500 0.3703(8) 0.098(5) Uani 1 2 d S
C41 C 0.0073(6) 0.7500 0.2288(10) 0.043(3) Uani 1 2 d S
S2 S 0.31291(14) 0.7500 0.1381(2) 0.0393(7) Uani 1 2 d S
F4 F 0.3482(4) 0.7500 0.3297(6) 0.066(2) Uani 1 2 d S
F3 F 0.2646(3) 0.6403(6) 0.3030(4) 0.0670(16) Uani 1 1 d .
O4 O 0.2533(4) 0.7500 0.0938(8) 0.068(3) Uani 1 2 d S
O3 O 0.3476(3) 0.6257(6) 0.1242(4) 0.0490(15) Uani 1 1 d .
C31 C 0.2968(6) 0.7500 0.2756(10) 0.042(3) Uani 1 2 d S
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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'
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
C1 I1 N1 85.7(3) . .
C1 I1 N2 86.8(3) . .
N1 I1 N2 172.4(3) . .
C21 N1 C21 118.7(8) . 8_565
C21 N1 I1 120.6(4) . .
C21 N1 I1 120.6(4) 8_565 .
C11 N2 C11 118.3(8) . 8_565
C11 N2 I1 120.8(4) . .
C11 N2 I1 120.8(4) 8_565 .
C13 N3 C14 121.9(4) . .
C13 N3 C14 121.9(4) . 8_565
C14 N3 C14 116.0(9) . 8_565
C23 N4 C24 121.0(5) . 8_565
C23 N4 C24 121.0(5) . .
C24 N4 C24 117.9(9) 8_565 .
N2 C11 C12 122.6(7) . .
N2 C11 H5A 118.7 . .
C12 C11 H5A 118.7 . .
C2 C1 C2 123.5(10) . 8_565
C2 C1 I1 118.3(5) . .
C2 C1 I1 118.3(5) 8_565 .
N1 C21 C22 122.7(7) . .
N1 C21 H11A 118.7 . .
C22 C21 H11A 118.7 . .
C1 C2 C3 117.1(8) . .
C1 C2 H10A 121.4 . .
C3 C2 H10A 121.4 . .
C21 C22 C23 119.9(7) . .
C21 C22 H10B 120.1 . .
C23 C22 H10B 120.1 . .
C11 C12 C13 120.3(7) . .
C11 C12 H18A 119.8 . .
C13 C12 H18A 119.8 . .
N4 C23 C22 121.9(5) . .
N4 C23 C22 121.9(5) . 8_565
C22 C23 C22 116.2(9) . 8_565
N3 C13 C12 122.2(4) . .
N3 C13 C12 122.2(4) . 8_565
C12 C13 C12 115.7(9) . 8_565
C4 C3 C2 121.0(9) . .
C4 C3 H20O 119.5 . .
C2 C3 H20O 119.5 . .
N4 C24 H20C 109.5 . .
N4 C24 H20D 109.5 . .
H20C C24 H20D 109.5 . .
N4 C24 H20E 109.5 . .
H20C C24 H20E 109.5 . .
H20D C24 H20E 109.5 . .
N3 C14 H20F 109.5 . .
N3 C14 H20G 109.5 . .
H20F C14 H20G 109.5 . .
N3 C14 H20H 109.5 . .
H20F C14 H20H 109.5 . .
H20G C14 H20H 109.5 . .
C3 C4 C3 120.3(10) . 8_565
C3 C4 H20B 119.9 . .
C3 C4 H20B 119.9 8_565 .
O1 S1 O1 116.0(6) 8_575 .
O1 S1 O2 114.0(4) 8_575 .
O1 S1 O2 114.0(4) . .
O1 S1 C41 104.1(4) 8_575 .
O1 S1 C41 104.1(4) . .
O2 S1 C41 102.6(7) . .
F2 C41 F2 109.7(11) 8_575 .
F2 C41 F1 105.7(8) 8_575 .
F2 C41 F1 105.7(8) . .
F2 C41 S1 112.5(7) 8_575 .
F2 C41 S1 112.5(7) . .
F1 C41 S1 110.3(10) . .
O4 S2 O3 115.4(3) . .
O4 S2 O3 115.4(3) . 8_575
O3 S2 O3 114.5(5) . 8_575
O4 S2 C31 102.9(6) . .
O3 S2 C31 103.0(3) . .
O3 S2 C31 103.0(3) 8_575 .
F4 C31 F3 107.7(8) . 8_575
F4 C31 F3 107.7(8) . .
F3 C31 F3 107.2(10) 8_575 .
F4 C31 S2 111.2(8) . .
F3 C31 S2 111.5(7) 8_575 .
F3 C31 S2 111.5(7) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
I1 C1 2.104(10) .
I1 N1 2.185(8) .
I1 N2 2.217(8) .
N1 C21 1.349(8) .
N1 C21 1.349(8) 8_565
N2 C11 1.348(8) .
N2 C11 1.348(8) 8_565
N3 C13 1.341(13) .
N3 C14 1.458(9) .
N3 C14 1.458(9) 8_565
N4 C23 1.346(13) .
N4 C24 1.465(9) 8_565
N4 C24 1.465(9) .
C11 C12 1.366(10) .
C11 H5A 0.9500 .
C1 C2 1.380(9) .
C1 C2 1.380(9) 8_565
C21 C22 1.359(10) .
C21 H11A 0.9500 .
C2 C3 1.399(11) .
C2 H10A 0.9500 .
C22 C23 1.424(9) .
C22 H10B 0.9500 .
C12 C13 1.418(9) .
C12 H18A 0.9500 .
C23 C22 1.424(9) 8_565
C13 C12 1.418(9) 8_565
C3 C4 1.370(11) .
C3 H20O 0.9500 .
C24 H20C 0.9800 .
C24 H20D 0.9800 .
C24 H20E 0.9800 .
C14 H20F 0.9800 .
C14 H20G 0.9800 .
C14 H20H 0.9800 .
C4 C3 1.370(11) 8_565
C4 H20B 0.9500 .
S1 O1 1.414(6) 8_575
S1 O1 1.414(6) .
S1 O2 1.418(11) .
S1 C41 1.822(13) .
F1 C41 1.311(16) .
F2 C41 1.303(9) .
C41 F2 1.303(9) 8_575
S2 O4 1.427(9) .
S2 O3 1.442(6) .
S2 O3 1.442(6) 8_575
S2 C31 1.835(13) .
F4 C31 1.328(14) .
F3 C31 1.330(9) .
C31 F3 1.330(9) 8_575
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_4
C1 I1 N1 C21 88.4(6) . .
N2 I1 N1 C21 88.4(6) . .
C1 I1 N1 C21 -88.4(6) . 8_565
N2 I1 N1 C21 -88.4(6) . 8_565
C1 I1 N2 C11 -87.2(7) . .
N1 I1 N2 C11 -87.2(7) . .
C1 I1 N2 C11 87.2(7) . 8_565
N1 I1 N2 C11 87.2(7) . 8_565
C11 N2 C11 C12 3.7(14) 8_565 .
I1 N2 C11 C12 178.2(5) . .
N1 I1 C1 C2 89.9(7) . .
N2 I1 C1 C2 -90.1(7) . .
N1 I1 C1 C2 -89.9(7) . 8_565
N2 I1 C1 C2 90.1(7) . 8_565
C21 N1 C21 C22 -1.6(14) 8_565 .
I1 N1 C21 C22 -178.4(6) . .
C2 C1 C2 C3 -0.9(16) 8_565 .
I1 C1 C2 C3 179.2(6) . .
N1 C21 C22 C23 1.0(12) . .
N2 C11 C12 C13 -0.7(12) . .
C24 N4 C23 C22 178.4(9) 8_565 .
C24 N4 C23 C22 3.5(16) . .
C24 N4 C23 C22 -3.5(16) 8_565 8_565
C24 N4 C23 C22 -178.4(9) . 8_565
C21 C22 C23 N4 177.9(9) . .
C21 C22 C23 C22 -0.3(14) . 8_565
C14 N3 C13 C12 -2.9(15) . .
C14 N3 C13 C12 -177.1(8) 8_565 .
C14 N3 C13 C12 177.1(8) . 8_565
C14 N3 C13 C12 2.9(15) 8_565 8_565
C11 C12 C13 N3 177.8(8) . .
C11 C12 C13 C12 -2.2(13) . 8_565
C1 C2 C3 C4 0.5(14) . .
C2 C3 C4 C3 -0.2(18) . 8_565
O1 S1 C41 F2 -56.8(10) 8_575 8_575
O1 S1 C41 F2 -178.7(9) . 8_575
O2 S1 C41 F2 62.2(9) . 8_575
O1 S1 C41 F2 178.7(9) 8_575 .
O1 S1 C41 F2 56.8(10) . .
O2 S1 C41 F2 -62.2(9) . .
O1 S1 C41 F1 61.0(4) 8_575 .
O1 S1 C41 F1 -61.0(4) . .
O2 S1 C41 F1 180.0 . .
O4 S2 C31 F4 180.0 . .
O3 S2 C31 F4 59.7(3) . .
O3 S2 C31 F4 -59.7(3) 8_575 .
O4 S2 C31 F3 -59.9(7) . 8_575
O3 S2 C31 F3 179.8(7) . 8_575
O3 S2 C31 F3 60.5(8) 8_575 8_575
O4 S2 C31 F3 59.9(7) . .
O3 S2 C31 F3 -60.5(8) . .
O3 S2 C31 F3 -179.8(7) 8_575 .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 15783561
