#------------------------------------------------------------------------------
#$Date: 2025-08-20 22:19:29 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301836 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/30/22/4302219.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_4302219
loop_
_publ_author_name
'Victor N. Nemykin'
'Alexey Y. Koposov'
'Brian C. Netzel'
'Mekhman S. Yusubov'
'Viktor V. Zhdankin'
_publ_contact_author_address
; 
 Department of Chemistry, 
 University of Minnesota Duluth, 
 1039 University Drive, 
 Duluth, MN, 55812. 
;
_publ_contact_author_email       vnemykin@d.umn.edu
_publ_contact_author_fax         '+1 218 7267394'
_publ_contact_author_name        'Victor N. Nemykin'
_publ_contact_author_phone       '+1 218 7266729'
_publ_section_title
;
Self-Assembly of Hydroxy(phenyl)iodonium Ions in Acidic Aqueous Solution:
Preparation, and X-ray Crystal Structures of Oligomeric Phenyliodine(III)
Sulfates
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              4908
_journal_page_last               4917
_journal_paper_doi               10.1021/ic900282k
_journal_volume                  48
_journal_year                    2009
_chemical_formula_moiety         'C16 H16 I2 O5'
_chemical_formula_sum            'C16 H16 I2 O5'
_chemical_formula_weight         542.11
_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
_audit_creation_date             05-06-01
_audit_creation_method           CRYSTALS_ver_12.39
_cell_angle_alpha                90
_cell_angle_beta                 107.36(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.946(4)
_cell_length_b                   9.383(3)
_cell_length_c                   17.097(4)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298
_cell_measurement_theta_max      13
_cell_measurement_theta_min      10
_cell_volume                     1829.1(10)
_computing_cell_refinement       'Win AFC'
_computing_data_collection       'Win AFC'
_computing_data_reduction        'TeXsan 10.3.b'
_computing_molecular_graphics    'CAMERON (Watkin et al 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al 2003)'
_computing_structure_solution    'SHELXS 86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      298
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku AFC-7R'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.000
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            4458
_diffrn_reflns_theta_full        27.521
_diffrn_reflns_theta_max         27.521
_diffrn_reflns_theta_min         2.504
_diffrn_standards_decay_%        92.70
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    3.459
_exptl_absorpt_correction_T_max  0.50
_exptl_absorpt_correction_T_min  0.38
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details
; 
 Azimutal absorption correction (North et al, 1968) 
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.968
_exptl_crystal_description       block
_exptl_crystal_F_000             1032
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         5.04
_refine_diff_density_min         -2.59
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.3556
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2532
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1738
_refine_ls_R_factor_gt           0.1249
_refine_ls_shift/su_max          0.000039
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 p=P(6)*max(Fo²,0) + (1-P(6))Fc² 
 Method = SHELXL 97 (Sheldrick, 1997) 
 W = 1. / [Sigma²(F*)+(P(1)p)²+P(2)p+P(4)+P(5)Sin(theta) ] 
 P(i) are: 
 0.200 0.00 0.00 0.00 0.00 0.333 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         2.5011
_refine_ls_wR_factor_gt          0.3041
_refine_ls_wR_factor_ref         0.3041
_reflns_limit_h_max              14
_reflns_limit_h_min              -15
_reflns_limit_k_max              12
_reflns_limit_k_min              0
_reflns_limit_l_max              22
_reflns_limit_l_min              0
_reflns_number_gt                2532
_reflns_number_total             4196
_reflns_threshold_expression     I>3.00u(I)
_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00
_oxford_refine_ls_scale          0.2644(11)
_oxford_structure_analysis_title 'XYZN file = SHELXL INS file, from DIRDIF out'
_cod_data_source_file            ic900282k_si_002.cif
_cod_data_source_block           CRYSTALS_cif
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_Hall     '-P 2ybc '
_cod_original_sg_symbol_H-M      'P 1 21/c 1 '
_cod_database_code               4302219
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x,y+1/2,-z+1/2
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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
I1 I 0.17565(12) -0.00244(14) 0.06477(7) 0.0394 1.0000 Uani . . . . . .
I2 I 0.41682(12) -0.20076(14) 0.05431(7) 0.0376 1.0000 Uani . . . . . .
O3 O 0.0998(14) 0.1650(17) 0.1249(9) 0.0475 1.0000 Uani . . . . . .
O4 O 0.6473(19) -0.0719(19) 0.0516(14) 0.0782 1.0000 Uani . . . . . .
O5 O 0.6042(15) -0.2707(16) 0.1056(10) 0.0517 1.0000 Uani . . . . . .
O6 O 0.0795(19) 0.2692(18) 0.0050(10) 0.0659 1.0000 Uani . . . . . .
O7 O 0.2408(11) -0.1785(15) 0.0228(9) 0.0373 1.0000 Uani . . . . . .
C8 C 0.124(3) -0.223(2) 0.1770(16) 0.0609 1.0000 Uani . . . . . .
C9 C 0.390(3) -0.513(3) 0.0710(15) 0.0616 1.0000 Uani . . . . . .
C10 C 0.399(2) -0.385(3) 0.1965(11) 0.0448 1.0000 Uani . . . . . .
C11 C 0.678(2) -0.174(3) 0.0930(11) 0.0434 1.0000 Uani . . . . . .
C12 C 0.377(3) -0.642(3) 0.1131(19) 0.0719 1.0000 Uani . . . . . .
C13 C 0.1883(15) -0.102(3) 0.1763(11) 0.0370 1.0000 Uani . . . . . .
C14 C 0.025(3) 0.396(3) 0.106(2) 0.0834 1.0000 Uani . . . . . .
C15 C 0.373(2) -0.635(3) 0.1919(19) 0.0690 1.0000 Uani . . . . . .
C16 C 0.3980(17) -0.392(2) 0.1168(11) 0.0358 1.0000 Uani . . . . . .
C17 C 0.283(3) -0.122(3) 0.3221(14) 0.0706 1.0000 Uani . . . . . .
C18 C 0.210(2) -0.238(3) 0.3230(15) 0.0565 1.0000 Uani . . . . . .
C19 C 0.383(2) -0.507(3) 0.2311(16) 0.0581 1.0000 Uani . . . . . .
C20 C 0.127(3) -0.290(3) 0.2501(17) 0.0747 1.0000 Uani . . . . . .
C21 C 0.068(2) 0.273(2) 0.0736(17) 0.0487 1.0000 Uani . . . . . .
C22 C 0.802(2) -0.203(4) 0.1404(16) 0.0783 1.0000 Uani . . . . . .
C24 C 0.260(2) -0.050(3) 0.2428(16) 0.0507 1.0000 Uani . . . . . .
H81 H 0.0739 -0.2631 0.1238 0.0709 1.0000 Uiso R . . . . .
H91 H 0.3924 -0.5117 0.0130 0.0711 1.0000 Uiso R . . . . .
H101 H 0.4129 -0.2933 0.2275 0.0545 1.0000 Uiso R . . . . .
H121 H 0.3722 -0.7361 0.0846 0.0812 1.0000 Uiso R . . . . .
H151 H 0.3621 -0.7242 0.2207 0.0793 1.0000 Uiso R . . . . .
H171 H 0.3466 -0.0906 0.3718 0.0805 1.0000 Uiso R . . . . .
H181 H 0.2170 -0.2854 0.3767 0.0691 1.0000 Uiso R . . . . .
H191 H 0.3771 -0.5054 0.2883 0.0672 1.0000 Uiso R . . . . .
H201 H 0.0731 -0.3710 0.2519 0.0930 1.0000 Uiso R . . . . .
H241 H 0.3020 0.0411 0.2400 0.0627 1.0000 Uiso R . . . . .
H221 H 0.8517 -0.1305 0.1293 0.0935 1.0000 Uiso R . . . . .
H222 H 0.8236 -0.2941 0.1244 0.0935 1.0000 Uiso R . . . . .
H223 H 0.8094 -0.2035 0.1980 0.0935 1.0000 Uiso R . . . . .
H141 H 0.0049 0.4692 0.0648 0.0978 1.0000 Uiso R . . . . .
H142 H 0.0818 0.4322 0.1541 0.0978 1.0000 Uiso R . . . . .
H143 H -0.0444 0.3675 0.1194 0.0978 1.0000 Uiso R . . . . .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
I -0.4742 1.8119 20.1472 4.3470 18.9949 0.3814 7.5138 27.7660 2.2735 66.8776
4.0712 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508
'International Tables Vol C 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
I2 . I1 . O3 . 149.7(4) yes
O3 . I1 . O7 . 170.9(6) yes
I2 . I1 . C13 . 88.4(5) yes
O3 . I1 . C13 . 79.8(7) yes
O7 . I1 . C13 . 91.5(7) yes
I1 . I2 . O5 . 151.7(4) yes
O5 . I2 . O7 . 166.4(6) yes
I1 . I2 . C16 . 102.2(5) yes
O5 . I2 . C16 . 78.5(7) yes
O7 . I2 . C16 . 87.9(7) yes
I1 . O3 . C21 . 108.2(13) yes
I2 . O5 . C11 . 111.9(14) yes
I1 . O7 . I2 . 117.7(7) yes
C13 . C8 . C20 . 121(3) yes
C13 . C8 . H81 . 119.081 no
C20 . C8 . H81 . 119.677 no
C12 . C9 . C16 . 114(2) yes
C12 . C9 . H91 . 123.139 no
C16 . C9 . H91 . 122.451 no
C16 . C10 . C19 . 117(2) yes
C16 . C10 . H101 . 121.549 no
C19 . C10 . H101 . 121.843 no
O5 . C11 . O4 . 123(2) yes
O5 . C11 . C22 . 113(2) yes
O4 . C11 . C22 . 124(3) yes
C9 . C12 . C15 . 119(3) yes
C9 . C12 . H121 . 119.662 no
C15 . C12 . H121 . 120.889 no
C8 . C13 . I1 . 119.4(16) yes
C8 . C13 . C24 . 122(2) yes
I1 . C13 . C24 . 118.6(17) yes
C21 . C14 . H141 . 109.213 no
C21 . C14 . H142 . 111.469 no
H141 . C14 . H142 . 109.476 no
C21 . C14 . H143 . 107.696 no
H141 . C14 . H143 . 109.476 no
H142 . C14 . H143 . 109.476 no
C12 . C15 . C19 . 121(2) yes
C12 . C15 . H151 . 119.440 no
C19 . C15 . H151 . 119.994 no
I2 . C16 . C9 . 114.4(16) yes
I2 . C16 . C10 . 119.5(17) yes
C9 . C16 . C10 . 126(2) yes
C18 . C17 . C24 . 115(2) yes
C18 . C17 . H171 . 122.518 no
C24 . C17 . H171 . 122.381 no
C17 . C18 . C20 . 122(2) yes
C17 . C18 . H181 . 118.399 no
C20 . C18 . H181 . 119.524 no
C15 . C19 . C10 . 123(2) yes
C15 . C19 . H191 . 118.321 no
C10 . C19 . H191 . 118.930 no
C18 . C20 . C8 . 117(3) yes
C18 . C20 . H201 . 121.303 no
C8 . C20 . H201 . 121.744 no
C14 . C21 . O3 . 115(2) yes
C14 . C21 . O6 . 123(3) yes
O3 . C21 . O6 . 121(2) yes
C11 . C22 . H221 . 109.931 no
C11 . C22 . H222 . 108.544 no
H221 . C22 . H222 . 109.476 no
C11 . C22 . H223 . 109.921 no
H221 . C22 . H223 . 109.476 no
H222 . C22 . H223 . 109.476 no
C17 . C24 . C13 . 122(2) yes
C17 . C24 . H241 . 118.758 no
C13 . C24 . H241 . 119.272 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
I1 . I2 . 3.479(2) yes
I1 . O3 . 2.214(15) yes
I1 . O7 . 2.045(13) yes
I1 . C13 . 2.089(18) yes
I2 . O5 . 2.245(17) yes
I2 . O7 . 2.020(13) yes
I2 . C16 . 2.13(2) yes
O3 . C21 . 1.32(3) yes
O4 . C11 . 1.18(3) yes
O5 . C11 . 1.33(3) yes
O6 . C21 . 1.22(3) yes
C8 . C13 . 1.37(3) yes
C8 . C20 . 1.39(4) yes
C8 . H81 . 1.000 no
C9 . C12 . 1.44(4) yes
C9 . C16 . 1.37(3) yes
C9 . H91 . 1.000 no
C10 . C16 . 1.36(3) yes
C10 . C19 . 1.33(3) yes
C10 . H101 . 1.000 no
C11 . C22 . 1.48(3) yes
C12 . C15 . 1.36(4) yes
C12 . H121 . 1.000 no
C13 . C24 . 1.30(3) yes
C14 . C21 . 1.44(3) yes
C14 . H141 . 0.960 no
C14 . H142 . 0.960 no
C14 . H143 . 0.960 no
C15 . C19 . 1.36(4) yes
C15 . H151 . 1.000 no
C17 . C18 . 1.40(4) yes
C17 . C24 . 1.46(3) yes
C17 . H171 . 1.000 no
C18 . C20 . 1.43(4) yes
C18 . H181 . 1.000 no
C19 . H191 . 1.000 no
C20 . H201 . 1.000 no
C22 . H221 . 0.960 no
C22 . H222 . 0.960 no
C22 . H223 . 0.960 no
C24 . H241 . 1.000 no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30660724
2 PubChem 101473428
