# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2219970'
loop_
_audit_author_name
_audit_author_address
'Keith F. White'
;La Trobe University
Australia
;
_audit_update_record             
;
2022-11-16 deposited with the CCDC.	2023-02-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        NO2PhICl(OTf)
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H4 Cl F3 I N O5 S'
_chemical_formula_weight         433.52

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -y, -z'

_cell_length_a                   6.8786(3)
_cell_length_b                   9.1760(3)
_cell_length_c                   21.5207(7)
_cell_angle_alpha                79.751(3)
_cell_angle_beta                 81.678(3)
_cell_angle_gamma                72.589(3)
_cell_volume                     1269.36(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    14546
_cell_measurement_theta_min      4.06
_cell_measurement_theta_max      71.2

_exptl_crystal_description       plate
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.268
_exptl_crystal_F_000             824
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    23.864
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.078
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, HyPix3000'
_diffrn_measurement_method       'w\ scans'
_diffrn_detector_area_resol_mean 10.0
_diffrn_reflns_number            24998
_diffrn_reflns_av_unetI/netI     0.0444
_diffrn_reflns_av_R_equivalents  0.0925
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         4.195
_diffrn_reflns_theta_max         71.768
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4916
_reflns_number_gt                4286
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_structure_solution    'SHELXT-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1308P)²+1.7353P] 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_number_reflns         4916
_refine_ls_number_parameters     343
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0690
_refine_ls_R_factor_gt           0.0641
_refine_ls_wR_factor_ref         0.1880
_refine_ls_wR_factor_gt          0.1814
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_restrained_S_all      1.100
_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
I01 I 0.48192(7) 0.61878(5) 0.10647(2) 0.04072(19) Uani 1 1 d . . . . .
I02 I 0.30030(8) -0.01509(5) 0.39277(2) 0.0468(2) Uani 1 1 d . . . . .
S1 S 0.8329(3) 0.8165(2) 0.08612(8) 0.0393(4) Uani 1 1 d . . . . .
S2 S 0.1825(3) -0.2168(2) 0.53270(9) 0.0479(5) Uani 1 1 d . . . . .
Cl1 Cl 0.2964(4) 0.4631(2) 0.08042(14) 0.0652(6) Uani 1 1 d . . . . .
Cl2 Cl 0.3342(4) 0.1829(2) 0.30938(11) 0.0626(6) Uani 1 1 d . . . . .
F3 F 0.4876(7) 1.0175(6) 0.0603(2) 0.0501(11) Uani 1 1 d . . . . .
F2 F 0.6373(8) 1.0743(5) 0.1296(2) 0.0512(11) Uani 1 1 d . . . . .
F1 F 0.7518(9) 1.1014(6) 0.0307(2) 0.0611(13) Uani 1 1 d . . . . .
O3 O 0.7028(8) 0.7407(6) 0.1344(2) 0.0406(11) Uani 1 1 d . . . . .
O8 O 0.2730(10) -0.2307(6) 0.4670(3) 0.0496(13) Uani 1 1 d . . . . .
F5 F 0.4029(10) -0.4963(6) 0.5659(3) 0.0674(15) Uani 1 1 d . . . . .
F6 F 0.3168(10) -0.3564(7) 0.6399(2) 0.0718(17) Uani 1 1 d . . . . .
O5 O 0.8551(9) 0.7673(7) 0.0255(3) 0.0504(13) Uani 1 1 d . . . . .
O4 O 1.0085(9) 0.8265(7) 0.1106(3) 0.0535(14) Uani 1 1 d . . . . .
O1 O 1.2745(9) -0.0433(7) 0.1789(3) 0.0558(15) Uani 1 1 d . . . . .
F4 F 0.5519(10) -0.3236(9) 0.5653(3) 0.0816(19) Uani 1 1 d . . . . .
O2 O 1.0782(10) -0.0481(7) 0.2660(3) 0.0577(16) Uani 1 1 d . . . . .
N1 N 1.1210(10) 0.0113(7) 0.2122(3) 0.0410(13) Uani 1 1 d . . . . .
O6 O 1.1604(12) -0.4742(8) 0.2427(3) 0.0710(19) Uani 1 1 d . . . . .
O10 O 0.0034(11) -0.2700(9) 0.5481(4) 0.0718(19) Uani 1 1 d . . . . .
O9 O 0.1673(13) -0.0728(7) 0.5515(3) 0.0686(19) Uani 1 1 d . . . . .
N2 N 1.1515(11) -0.4191(8) 0.2916(4) 0.0538(18) Uani 1 1 d . . . . .
O7 O 1.3007(11) -0.4269(9) 0.3184(4) 0.074(2) Uani 1 1 d . . . . .
C2 C 1.0043(11) 0.2157(8) 0.1234(3) 0.0385(15) Uani 1 1 d . . . . .
H2 H 1.115987 0.163645 0.096548 0.046 Uiso 1 1 calc R U . . .
C1 C 0.9788(11) 0.1584(8) 0.1877(3) 0.0375(15) Uani 1 1 d . . . . .
C5 C 0.6847(12) 0.3657(9) 0.2053(4) 0.0442(16) Uani 1 1 d . . . . .
H5 H 0.576160 0.419529 0.232609 0.053 Uiso 1 1 calc R U . . .
C13 C 0.5834(11) -0.1623(8) 0.3624(3) 0.0404(16) Uani 1 1 d . . . . .
C6 C 0.7078(10) 0.4196(8) 0.1413(3) 0.0354(14) Uani 1 1 d . . . . .
C4 C 0.8654(12) 0.3482(9) 0.0997(3) 0.0420(16) Uani 1 1 d . . . . .
H4 H 0.877105 0.389668 0.056039 0.050 Uiso 1 1 calc R U . . .
C3 C 0.8242(13) 0.2312(9) 0.2283(4) 0.0449(17) Uani 1 1 d . . . . .
H3 H 0.812645 0.189722 0.271903 0.054 Uiso 1 1 calc R U . . .
C7 C 0.6671(12) 1.0157(9) 0.0765(4) 0.0416(16) Uani 1 1 d . . . . .
C10 C 0.9304(14) -0.2962(10) 0.3787(4) 0.0485(18) Uani 1 1 d . . . . .
H10 H 1.043229 -0.329318 0.403548 0.058 Uiso 1 1 calc R U . . .
C8 C 0.9469(12) -0.3348(8) 0.3187(4) 0.0422(16) Uani 1 1 d . . . . .
C11 C 0.6036(12) -0.2074(10) 0.3025(4) 0.0461(17) Uani 1 1 d . . . . .
H11 H 0.490681 -0.179344 0.277841 0.055 Uiso 1 1 calc R U . . .
C9 C 0.7902(14) -0.2925(9) 0.2811(4) 0.0499(19) Uani 1 1 d . . . . .
H9 H 0.812025 -0.322657 0.240080 0.060 Uiso 1 1 calc R U . . .
C12 C 0.7371(14) -0.2049(10) 0.4013(4) 0.0467(18) Uani 1 1 d . . . . .
H12 H 0.714940 -0.174153 0.442250 0.056 Uiso 1 1 calc R U . . .
C14 C 0.3772(15) -0.3580(10) 0.5782(4) 0.053(2) 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
I01 C6 2.114(6) . ?
I01 O3 2.332(5) . ?
I01 Cl1 2.359(2) . ?
I02 C13 2.101(7) . ?
I02 O8 2.348(5) . ?
I02 Cl2 2.3555(19) . ?
S1 O4 1.419(6) . ?
S1 O5 1.428(6) . ?
S1 O3 1.486(5) . ?
S1 C7 1.836(8) . ?
S2 O9 1.419(7) . ?
S2 O10 1.431(8) . ?
S2 O8 1.471(6) . ?
S2 C14 1.823(9) . ?
F3 C7 1.325(9) . ?
F2 C7 1.313(9) . ?
F1 C7 1.328(8) . ?
F5 C14 1.298(11) . ?
F6 C14 1.333(10) . ?
O1 N1 1.214(9) . ?
F4 C14 1.311(12) . ?
O2 N1 1.223(8) . ?
N1 C1 1.471(9) . ?
O6 N2 1.233(11) . ?
N2 O7 1.226(11) . ?
N2 C8 1.480(11) . ?
C2 C4 1.370(10) . ?
C2 C1 1.395(10) . ?
C1 C3 1.362(11) . ?
C5 C3 1.378(11) . ?
C5 C6 1.381(10) . ?
C13 C12 1.366(11) . ?
C13 C11 1.398(11) . ?
C6 C4 1.382(11) . ?
C10 C8 1.378(12) . ?
C10 C12 1.413(13) . ?
C8 C9 1.364(12) . ?
C11 C9 1.351(12) . ?

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
C6 I01 O3 81.7(2) . . ?
C6 I01 Cl1 90.4(2) . . ?
O3 I01 Cl1 171.91(14) . . ?
C13 I02 O8 84.2(2) . . ?
C13 I02 Cl2 91.98(19) . . ?
O8 I02 Cl2 173.50(15) . . ?
O4 S1 O5 119.1(4) . . ?
O4 S1 O3 112.5(3) . . ?
O5 S1 O3 112.6(3) . . ?
O4 S1 C7 104.3(4) . . ?
O5 S1 C7 105.2(3) . . ?
O3 S1 C7 100.5(3) . . ?
O9 S2 O10 115.9(5) . . ?
O9 S2 O8 113.6(4) . . ?
O10 S2 O8 112.9(4) . . ?
O9 S2 C14 105.4(5) . . ?
O10 S2 C14 105.2(4) . . ?
O8 S2 C14 102.1(4) . . ?
S1 O3 I01 122.2(3) . . ?
S2 O8 I02 122.2(3) . . ?
O1 N1 O2 123.6(6) . . ?
O1 N1 C1 118.9(6) . . ?
O2 N1 C1 117.5(6) . . ?
O7 N2 O6 124.5(8) . . ?
O7 N2 C8 118.0(8) . . ?
O6 N2 C8 117.5(8) . . ?
C4 C2 C1 118.9(7) . . ?
C3 C1 C2 122.6(7) . . ?
C3 C1 N1 118.6(6) . . ?
C2 C1 N1 118.7(6) . . ?
C3 C5 C6 117.8(7) . . ?
C12 C13 C11 124.1(7) . . ?
C12 C13 I02 118.4(6) . . ?
C11 C13 I02 117.5(6) . . ?
C5 C6 C4 123.6(6) . . ?
C5 C6 I01 117.0(5) . . ?
C4 C6 I01 119.3(5) . . ?
C2 C4 C6 117.8(6) . . ?
C1 C3 C5 119.2(7) . . ?
F2 C7 F3 108.8(6) . . ?
F2 C7 F1 109.7(7) . . ?
F3 C7 F1 108.4(6) . . ?
F2 C7 S1 110.7(5) . . ?
F3 C7 S1 109.4(5) . . ?
F1 C7 S1 109.7(5) . . ?
C8 C10 C12 116.7(7) . . ?
C9 C8 C10 124.4(8) . . ?
C9 C8 N2 117.6(7) . . ?
C10 C8 N2 117.9(7) . . ?
C9 C11 C13 117.3(8) . . ?
C11 C9 C8 119.6(8) . . ?
C13 C12 C10 117.8(7) . . ?
F5 C14 F4 109.2(8) . . ?
F5 C14 F6 108.1(7) . . ?
F4 C14 F6 109.2(8) . . ?
F5 C14 S2 111.2(7) . . ?
F4 C14 S2 110.2(6) . . ?
F6 C14 S2 108.9(6) . . ?

_refine_diff_density_max         2.542
_refine_diff_density_min         -1.676
_refine_diff_density_rms         0.215

# start Validation Reply Form
_vrf_PLAT971_shelx               
;
PROBLEM: Check Calcd Resid. Dens.  0.93Ang From I01             2.55 eA-3  
RESPONSE: This alert has arisen as a result of residual electron density 
in close proximity to an iodine atom. Each iodine atom in the ASU has
some unassigned residual electron density. 
;
# end Validation Reply Form

