#------------------------------------------------------------------------------
#$Date: 2025-07-05 13:10:14 +0300 (Sat, 05 Jul 2025) $
#$Revision: 300370 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/88/1568824.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_1568824
loop_
_publ_author_name
'Abdul Manan, Mohd Abdul Fatah'
'Cordes, David B.'
'Slawin, Alexandra M. Z.'
'O'Hagan, David'
_publ_section_title
;
 [3-Methoxy-5-(methoxycarbonyl)isoxazol-4-yl](4-methoxyphenyl)iodonium
 2,2,2-trifluoroacetate
;
_journal_coeditor_code           TK4090
_journal_issue                   4
_journal_name_full               IUCrData
_journal_page_first              x230300
_journal_paper_doi               10.1107/S2414314623003000
_journal_volume                  8
_journal_year                    2023
_chemical_formula_iupac          'C13 H13 I1 N1 O5 +, C2 F3 O2 -'
_chemical_formula_moiety         'C13 H13 I1 N1 O5 +, C2 F3 O2 -'
_chemical_formula_sum            'C15 H13 F3 I N O7'
_chemical_formula_weight         503.17
_chemical_name_systematic
;
[3-Methoxy-5-(methoxycarbonyl)isoxazol-4-yl](4-methoxyphenyl)iodonium
2,2,2-trifluoroacetate
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                113.913(5)
_cell_angle_beta                 97.392(4)
_cell_angle_gamma                98.975(5)
_cell_formula_units_Z            2
_cell_length_a                   8.436(2)
_cell_length_b                   10.750(3)
_cell_length_c                   11.338(3)
_cell_measurement_reflns_used    1722
_cell_measurement_temperature    173
_cell_measurement_theta_max      25.30
_cell_measurement_theta_min      2.00
_cell_volume                     907.2(4)
_computing_cell_refinement
;
CrystalClear (Rigaku, 2014)
;
_computing_data_collection
;
CrystalClear (Rigaku, 2014)
;
_computing_data_reduction
;
CrystalClear (Rigaku, 2014)
;
_computing_molecular_graphics
;
Olex2 (Dolomanov et al.,  2009) and Mercury (Macrae et
al.,  2020)
;
_computing_publication_material
;
CrystalStructure (Rigaku, 2018), enCIFer (Allen et al.,
2004)
and
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015)
;
_computing_structure_solution
;
DIRDIF99 (Beurskens et al.,  1999)
;
_diffrn_ambient_temperature      173
_diffrn_detector                 'hybrid photon counting detector'
_diffrn_detector_area_resol_mean 5.814
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device       'AFC10: Fixed χ 3 circle'
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_measurement_specimen_support Loop
_diffrn_radiation_monochromator  'Rigaku Osmic Confocal Optical System'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0528
_diffrn_reflns_av_unetI/netI     0.0591
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11079
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.356
_diffrn_reflns_theta_min         2.011
_diffrn_source                   'Rotating Anode'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.833
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_correction_T_min  0.862
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrystalClear; Rigaku, 2014)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.842
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             492.00
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.010
_refine_diff_density_max         1.485
_refine_diff_density_min         -0.647
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3270
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0925
_refine_ls_R_factor_gt           0.0601
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0635P)²+4.1326P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1307
_refine_ls_wR_factor_ref         0.1445
_reflns_number_gt                2423
_reflns_number_total             3270
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            tk4090.cif
_cod_data_source_block           I
_cod_database_code               1568824
#BEGIN Tags that were not found in dictionaries:
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
#END Tags that were not found in dictionaries
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I I4 0.20970(6) 0.42981(5) 0.12013(5) 0.0509(2) Uani d 1 . .
F F16 0.2459(9) 0.9270(9) 0.2807(8) 0.152(4) Uani d 1 . .
F F17 0.0378(8) 0.9854(6) 0.3427(6) 0.111(3) Uani d 1 . .
F F18 0.1490(12) 0.8548(8) 0.4008(6) 0.136(3) Uani d 1 . .
O O1 0.4332(8) 0.6834(6) 0.5238(5) 0.0632(16) Uani d 1 . .
O O3 0.5054(8) 0.7371(7) 0.2570(7) 0.0717(18) Uani d 1 . .
O O6 0.1162(9) 0.3812(7) 0.3838(7) 0.0777(19) Uani d 1 . .
O O7 0.2682(9) 0.4996(8) 0.5853(7) 0.081(2) Uani d 1 . .
O O12 0.7116(10) 0.0695(8) 0.1381(8) 0.094(2) Uani d 1 . .
O O17 -0.0913(8) 0.7775(6) 0.1053(6) 0.076(2) Uani d 1 . .
O O18 0.0342(9) 0.6423(7) 0.1656(7) 0.086(2) Uani d 1 . .
N N2 0.5171(10) 0.7647(9) 0.4715(8) 0.074(2) Uani d 1 . .
C C3 0.4577(11) 0.6993(9) 0.3442(9) 0.061(3) Uani d 1 . .
C C4 0.3342(10) 0.5742(9) 0.3109(8) 0.057(2) Uani d 1 . .
C C5 0.3256(11) 0.5714(10) 0.4265(9) 0.064(2) Uani d 1 . .
C C6 0.2232(12) 0.4716(11) 0.4574(9) 0.064(3) Uani d 1 . .
C C7 0.1665(14) 0.4074(13) 0.6255(13) 0.095(4) Uani d 1 . .
H H7A 0.165550 0.309983 0.568918 0.143 Uiso calc 1 . .
H H7B 0.054106 0.421058 0.616962 0.143 Uiso calc 1 . .
H H7C 0.211381 0.429339 0.717581 0.143 Uiso calc 1 . .
C C8 0.6252(12) 0.8788(11) 0.3162(11) 0.084(3) Uani d 1 . .
H H8A 0.723922 0.876368 0.370487 0.126 Uiso calc 1 . .
H H8B 0.573436 0.950570 0.371279 0.126 Uiso calc 1 . .
H H8C 0.655593 0.900916 0.245180 0.126 Uiso calc 1 . .
C C9 0.3799(11) 0.3064(9) 0.1113(8) 0.055(2) Uani d 1 . .
C C10 0.3599(15) 0.2162(11) 0.1705(9) 0.080(3) Uani d 1 . .
H H10 0.267985 0.210169 0.209962 0.096 Uiso calc 1 . .
C C11 0.4686(15) 0.1368(12) 0.1732(10) 0.083(3) Uani d 1 . .
H H11 0.447999 0.068052 0.205282 0.099 Uiso calc 1 . .
C C12 0.5986(13) 0.1563(11) 0.1318(11) 0.070(3) Uani d 1 . .
C C13 0.6360(12) 0.2401(12) 0.0699(11) 0.090(4) Uani d 1 . .
H H13 0.733464 0.245200 0.036741 0.108 Uiso calc 1 . .
C C14 0.5113(13) 0.3240(11) 0.0579(10) 0.077(3) Uani d 1 . .
H H14 0.524458 0.384409 0.015910 0.093 Uiso calc 1 . .
C C15 0.8561(13) 0.1021(16) 0.1053(14) 0.137(7) Uani d 1 . .
H H15A 0.925082 0.038937 0.112025 0.206 Uiso calc 1 . .
H H15B 0.835017 0.092238 0.014517 0.206 Uiso calc 1 . .
H H15C 0.912545 0.198818 0.165580 0.206 Uiso calc 1 . .
C C16 0.1083(10) 0.8821(9) 0.3002(8) 0.056(2) Uani d 1 . .
C C17 0.0083(9) 0.7542(9) 0.1774(8) 0.049(2) Uani d 1 . .
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, Tables 4.2.6.8 and 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)'
N N 0.0061 0.0033
'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)'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C9 I4 C4 . . 90.8(3) ?
C5 O1 N2 . . 110.3(7) ?
C3 O3 C8 . . 113.8(8) ?
C6 O7 C7 . . 114.1(9) ?
C15 O12 C12 . . 114.6(11) ?
C3 N2 O1 . . 104.8(8) ?
O3 C3 N2 . . 125.4(9) ?
O3 C3 C4 . . 123.4(8) ?
N2 C3 C4 . . 111.1(10) ?
C5 C4 C3 . . 104.5(8) ?
C5 C4 I4 . . 129.6(8) ?
C3 C4 I4 . . 125.8(7) ?
C4 C5 O1 . . 109.2(9) ?
C4 C5 C6 . . 130.6(9) ?
O1 C5 C6 . . 120.2(9) ?
O6 C6 O7 . . 123.9(10) ?
O6 C6 C5 . . 125.4(9) ?
O7 C6 C5 . . 110.8(9) ?
O7 C7 H7A . . 109.5 ?
O7 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
O7 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
O3 C8 H8A . . 109.5 ?
O3 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
O3 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
C14 C9 C10 . . 122.3(9) ?
C14 C9 I4 . . 119.7(7) ?
C10 C9 I4 . . 117.9(7) ?
C11 C10 C9 . . 121.3(11) ?
C11 C10 H10 . . 119.3 ?
C9 C10 H10 . . 119.3 ?
C12 C11 C10 . . 118.4(12) ?
C12 C11 H11 . . 120.8 ?
C10 C11 H11 . . 120.8 ?
C11 C12 C13 . . 127.0(11) ?
C11 C12 O12 . . 116.1(10) ?
C13 C12 O12 . . 116.5(10) ?
C12 C13 C14 . . 115.5(9) ?
C12 C13 H13 . . 122.2 ?
C14 C13 H13 . . 122.2 ?
C9 C14 C13 . . 115.1(10) ?
C9 C14 H14 . . 122.5 ?
C13 C14 H14 . . 122.5 ?
O12 C15 H15A . . 109.5 ?
O12 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
O12 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
F16 C16 F17 . . 107.8(9) ?
F16 C16 F18 . . 103.2(9) ?
F17 C16 F18 . . 105.7(8) ?
F16 C16 C17 . . 110.8(8) ?
F17 C16 C17 . . 115.2(7) ?
F18 C16 C17 . . 113.2(8) ?
O18 C17 O17 . . 128.3(8) ?
O18 C17 C16 . . 116.1(7) ?
O17 C17 C16 . . 115.6(7) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
I4 C9 . 2.087(8) ?
I4 C4 . 2.092(8) ?
F16 C16 . 1.268(11) ?
F17 C16 . 1.290(10) ?
F18 C16 . 1.307(11) ?
O1 C5 . 1.347(10) ?
O1 N2 . 1.397(10) ?
O3 C3 . 1.297(12) ?
O3 C8 . 1.520(11) ?
O6 C6 . 1.154(11) ?
O7 C6 . 1.344(11) ?
O7 C7 . 1.459(13) ?
O12 C15 . 1.355(12) ?
O12 C12 . 1.449(12) ?
O17 C17 . 1.221(9) ?
O18 C17 . 1.214(10) ?
N2 C3 . 1.308(12) ?
C3 C4 . 1.445(13) ?
C4 C5 . 1.334(13) ?
C5 C6 . 1.453(14) ?
C7 H7A . 0.9800 ?
C7 H7B . 0.9800 ?
C7 H7C . 0.9800 ?
C8 H8A . 0.9800 ?
C8 H8B . 0.9800 ?
C8 H8C . 0.9800 ?
C9 C14 . 1.353(13) ?
C9 C10 . 1.388(14) ?
C10 C11 . 1.353(14) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.268(15) ?
C11 H11 . 0.9500 ?
C12 C13 . 1.374(15) ?
C13 C14 . 1.515(16) ?
C13 H13 . 0.9500 ?
C14 H14 . 0.9500 ?
C15 H15A . 0.9800 ?
C15 H15B . 0.9800 ?
C15 H15C . 0.9800 ?
C16 C17 . 1.524(11) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C8 H8C O12 1_565 0.98 2.58 3.475(14) 152 yes
C11 H11 F16 1_545 0.95 2.56 3.405(17) 148 yes
C15 H15C O6 1_655 0.98 2.62 3.503(14) 151 yes
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C5 O1 N2 C3 . . . . 0.0(9) ?
C8 O3 C3 N2 . . . . -7.7(13) ?
C8 O3 C3 C4 . . . . 174.8(8) ?
O1 N2 C3 O3 . . . . -177.8(8) ?
O1 N2 C3 C4 . . . . -0.1(10) ?
O3 C3 C4 C5 . . . . 177.9(8) ?
N2 C3 C4 C5 . . . . 0.1(10) ?
O3 C3 C4 I4 . . . . 0.4(12) ?
N2 C3 C4 I4 . . . . -177.4(6) ?
C3 C4 C5 O1 . . . . -0.1(10) ?
I4 C4 C5 O1 . . . . 177.3(5) ?
C3 C4 C5 C6 . . . . 179.6(9) ?
I4 C4 C5 C6 . . . . -3.0(15) ?
N2 O1 C5 C4 . . . . 0.1(10) ?
N2 O1 C5 C6 . . . . -179.7(8) ?
C7 O7 C6 O6 . . . . -1.6(14) ?
C7 O7 C6 C5 . . . . 177.5(8) ?
C4 C5 C6 O6 . . . . -8.3(16) ?
O1 C5 C6 O6 . . . . 171.4(9) ?
C4 C5 C6 O7 . . . . 172.5(9) ?
O1 C5 C6 O7 . . . . -7.7(11) ?
C14 C9 C10 C11 . . . . -2.6(15) ?
I4 C9 C10 C11 . . . . -177.5(8) ?
C9 C10 C11 C12 . . . . 6.9(16) ?
C10 C11 C12 C13 . . . . -7.7(18) ?
C10 C11 C12 O12 . . . . 179.4(9) ?
C15 O12 C12 C11 . . . . -173.9(10) ?
C15 O12 C12 C13 . . . . 12.4(14) ?
C11 C12 C13 C14 . . . . 3.9(17) ?
O12 C12 C13 C14 . . . . 176.8(8) ?
C10 C9 C14 C13 . . . . -1.1(13) ?
I4 C9 C14 C13 . . . . 173.7(6) ?
C12 C13 C14 C9 . . . . 0.7(13) ?
F16 C16 C17 O18 . . . . 86.1(11) ?
F17 C16 C17 O18 . . . . -151.2(9) ?
F18 C16 C17 O18 . . . . -29.4(12) ?
F16 C16 C17 O17 . . . . -96.1(11) ?
F17 C16 C17 O17 . . . . 26.7(12) ?
F18 C16 C17 O17 . . . . 148.5(9) ?
