# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ydkr
_database_code_depnum_ccdc_archive 'CCDC 2416845'
loop_
_audit_author_name
_audit_author_address
'Tomohiro Agou'
;University of Hyogo
Japan
;
_audit_update_record             
;
2025-01-14 deposited with the CCDC.	2025-02-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H13 F2 I O2'
_chemical_formula_weight         342.11

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'
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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P n'
_space_group_name_Hall           'P -2yac'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y, z+1/2'

_cell_length_a                   8.0439(15)
_cell_length_b                   6.9280(13)
_cell_length_c                   11.632(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.98(2)
_cell_angle_gamma                90
_cell_volume                     636.4(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    914
_cell_measurement_theta_min      2.8720
_cell_measurement_theta_max      24.2100

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.785
_exptl_crystal_F_000             332
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.230
_exptl_absorpt_coefficient_mu    2.525
_shelx_estimated_absorpt_T_min   0.571
_shelx_estimated_absorpt_T_max   0.594
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.14899
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.839
_oxdiff_exptl_absorpt_empirical_full_max 2.183
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine focus sealed tube'
_diffrn_measurement_device_type  ccd
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2098
_diffrn_reflns_av_unetI/netI     0.0377
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.843
_diffrn_reflns_theta_max         25.470
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.567
_diffrn_reflns_point_group_measured_fraction_full 0.569
_reflns_number_total             1346
_reflns_number_gt                1191
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.130
_reflns_Friedel_fraction_max     0.131
_reflns_Friedel_fraction_full    0.135

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrystalClear-SM ver 2.1 (Rigaku)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    Yadokari-XG
_computing_publication_material  Yadokari-XG
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1041P)²+0.2406P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.10(7)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1346
_refine_ls_number_parameters     148
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0568
_refine_ls_R_factor_gt           0.0510
_refine_ls_wR_factor_ref         0.1579
_refine_ls_wR_factor_gt          0.1472
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.083
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.476(2) 0.2449(18) 0.4599(11) 0.049(3) Uani 1 1 d . . . . .
C2 C 0.4673(17) 0.0680(18) 0.5164(12) 0.060(3) Uani 1 1 d . . . . .
H8 H 0.3641 -0.0024 0.5019 0.072 Uiso 1 1 calc R U . . .
C3 C 0.6028(18) -0.006(2) 0.5917(16) 0.069(4) Uani 1 1 d . . . . .
H9 H 0.5930 -0.1272 0.6278 0.083 Uiso 1 1 calc R U . . .
C4 C 0.7553(16) 0.0944(19) 0.6165(11) 0.052(3) Uani 1 1 d . . . . .
C5 C 0.7688(18) 0.269(2) 0.5610(13) 0.053(3) Uani 1 1 d . . . . .
H10 H 0.8732 0.3372 0.5736 0.064 Uiso 1 1 calc R U . . .
C6 C 0.632(3) 0.340(3) 0.4894(17) 0.053(4) Uani 1 1 d . . . . .
H11 H 0.6422 0.4641 0.4562 0.063 Uiso 1 1 calc R U . . .
C7 C 0.327(3) 0.323(2) 0.3803(15) 0.050(4) Uani 1 1 d . . . . .
H7 H 0.2438 0.2152 0.3609 0.059 Uiso 1 1 calc R U . . .
C8 C 0.2361(14) 0.4867(17) 0.4258(10) 0.050(3) Uani 1 1 d . . . . .
C9 C 0.0926(16) 0.579(2) 0.3411(11) 0.057(3) Uani 1 1 d . . . . .
H13 H 0.1406 0.6412 0.2769 0.069 Uiso 1 1 calc R U . . .
C10 C -0.046(2) 0.436(2) 0.2855(14) 0.072(4) Uani 1 1 d . . . . .
H1 H 0.0072 0.3201 0.2602 0.108 Uiso 1 1 calc R U . . .
H2 H -0.1181 0.4963 0.2177 0.108 Uiso 1 1 calc R U . . .
H3 H -0.1146 0.4001 0.3432 0.108 Uiso 1 1 calc R U . . .
C11 C 1.0415(19) 0.111(2) 0.7283(14) 0.067(4) Uani 1 1 d . . . . .
H4 H 1.0969 0.1242 0.6606 0.101 Uiso 1 1 calc R U . . .
H5 H 1.1152 0.0381 0.7901 0.101 Uiso 1 1 calc R U . . .
H6 H 1.0199 0.2393 0.7577 0.101 Uiso 1 1 calc R U . . .
O1 O 0.8835(12) 0.0099(15) 0.6937(9) 0.062(2) Uani 1 1 d . . . . .
O2 O 0.3666(13) 0.3935(13) 0.2692(8) 0.058(2) Uani 1 1 d . . . . .
H12 H 0.3986 0.5090 0.2770 0.087 Uiso 1 1 calc R U . . .
F1 F 0.3512(10) 0.6244(11) 0.4720(8) 0.0642(19) Uani 1 1 d . . . . .
F2 F 0.1784(10) 0.4118(12) 0.5208(6) 0.0620(18) Uani 1 1 d . . . . .
I1 I -0.02151(9) 0.80295(12) 0.43135(9) 0.0777(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
C1 C2 1.399(18) . ?
C1 C6 1.40(2) . ?
C1 C7 1.47(3) . ?
C2 C3 1.361(19) . ?
C2 H8 0.9500 . ?
C3 C4 1.391(18) . ?
C3 H9 0.9500 . ?
C4 O1 1.364(15) . ?
C4 C5 1.39(2) . ?
C5 C6 1.34(3) . ?
C5 H10 0.9500 . ?
C6 H11 0.9500 . ?
C7 O2 1.47(2) . ?
C7 C8 1.50(2) . ?
C7 H7 1.0000 . ?
C8 F1 1.366(13) . ?
C8 F2 1.379(14) . ?
C8 C9 1.511(18) . ?
C9 C10 1.54(2) . ?
C9 I1 2.171(14) . ?
C9 H13 1.0000 . ?
C10 H1 0.9800 . ?
C10 H2 0.9800 . ?
C10 H3 0.9800 . ?
C11 O1 1.439(17) . ?
C11 H4 0.9800 . ?
C11 H5 0.9800 . ?
C11 H6 0.9800 . ?
O2 H12 0.8400 . ?

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
C2 C1 C6 114.9(14) . . ?
C2 C1 C7 120.7(13) . . ?
C6 C1 C7 124.4(12) . . ?
C3 C2 C1 121.7(13) . . ?
C3 C2 H8 119.1 . . ?
C1 C2 H8 119.1 . . ?
C2 C3 C4 120.8(13) . . ?
C2 C3 H9 119.6 . . ?
C4 C3 H9 119.6 . . ?
O1 C4 C5 124.4(11) . . ?
O1 C4 C3 116.7(11) . . ?
C5 C4 C3 118.9(12) . . ?
C6 C5 C4 119.0(14) . . ?
C6 C5 H10 120.5 . . ?
C4 C5 H10 120.5 . . ?
C5 C6 C1 124.6(17) . . ?
C5 C6 H11 117.7 . . ?
C1 C6 H11 117.7 . . ?
O2 C7 C1 112.7(16) . . ?
O2 C7 C8 105.2(11) . . ?
C1 C7 C8 116.8(14) . . ?
O2 C7 H7 107.2 . . ?
C1 C7 H7 107.2 . . ?
C8 C7 H7 107.2 . . ?
F1 C8 F2 104.7(9) . . ?
F1 C8 C7 109.1(12) . . ?
F2 C8 C7 105.1(11) . . ?
F1 C8 C9 109.6(10) . . ?
F2 C8 C9 110.5(9) . . ?
C7 C8 C9 117.0(12) . . ?
C8 C9 C10 113.7(11) . . ?
C8 C9 I1 109.2(8) . . ?
C10 C9 I1 109.0(9) . . ?
C8 C9 H13 108.3 . . ?
C10 C9 H13 108.3 . . ?
I1 C9 H13 108.3 . . ?
C9 C10 H1 109.5 . . ?
C9 C10 H2 109.5 . . ?
H1 C10 H2 109.5 . . ?
C9 C10 H3 109.5 . . ?
H1 C10 H3 109.5 . . ?
H2 C10 H3 109.5 . . ?
O1 C11 H4 109.5 . . ?
O1 C11 H5 109.5 . . ?
H4 C11 H5 109.5 . . ?
O1 C11 H6 109.5 . . ?
H4 C11 H6 109.5 . . ?
H5 C11 H6 109.5 . . ?
C4 O1 C11 119.5(11) . . ?
C7 O2 H12 109.5 . . ?

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
C6 C1 C2 C3 -2(2) . . . . ?
C7 C1 C2 C3 -178.9(16) . . . . ?
C1 C2 C3 C4 1(3) . . . . ?
C2 C3 C4 O1 179.5(15) . . . . ?
C2 C3 C4 C5 -2(2) . . . . ?
O1 C4 C5 C6 -178.1(15) . . . . ?
C3 C4 C5 C6 3(2) . . . . ?
C4 C5 C6 C1 -4(3) . . . . ?
C2 C1 C6 C5 3(3) . . . . ?
C7 C1 C6 C5 -179.5(14) . . . . ?
C2 C1 C7 O2 -133.3(13) . . . . ?
C6 C1 C7 O2 50(2) . . . . ?
C2 C1 C7 C8 104.7(16) . . . . ?
C6 C1 C7 C8 -72(2) . . . . ?
O2 C7 C8 F1 -76.3(15) . . . . ?
C1 C7 C8 F1 49.5(17) . . . . ?
O2 C7 C8 F2 171.9(11) . . . . ?
C1 C7 C8 F2 -62.3(17) . . . . ?
O2 C7 C8 C9 48.9(17) . . . . ?
C1 C7 C8 C9 174.7(13) . . . . ?
F1 C8 C9 C10 -179.1(11) . . . . ?
F2 C8 C9 C10 -64.2(14) . . . . ?
C7 C8 C9 C10 56.0(16) . . . . ?
F1 C8 C9 I1 -57.2(11) . . . . ?
F2 C8 C9 I1 57.7(11) . . . . ?
C7 C8 C9 I1 177.9(11) . . . . ?
C5 C4 O1 C11 5(2) . . . . ?
C3 C4 O1 C11 -176.5(15) . . . . ?

_refine_diff_density_max         1.036
_refine_diff_density_min         -1.176
_refine_diff_density_rms         0.112


# start Validation Reply Form
_vrf_PLAT342_ydkr                
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............     0.0224 Ang.  
RESPONSE: The obtained single crystals were very small,
and hence their X-ray diffractinon were weak
(especiallay in the higher diffraction angle region).
;
# end Validation Reply Form

