# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_mo_023WB108_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2125800'
loop_
_audit_author_name
_audit_author_address
'Merce Font Bardia'
;Universitat de Barcelona
Spain
;
_audit_update_record             
;
2021-12-02 deposited with the CCDC.	2022-03-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        Iododiflunisal
_chemical_name_common            IDIF
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H7 F2 I O3'
_chemical_formula_sum            'C13 H7 F2 I O3'
_chemical_formula_weight         376.09

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   16.9777(10)
_cell_length_b                   4.0424(2)
_cell_length_c                   18.0441(11)
_cell_angle_alpha                90
_cell_angle_beta                 93.412(2)
_cell_angle_gamma                90
_cell_volume                     1236.18(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9611
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      30.57

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.021
_exptl_crystal_F_000             720
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.348
_exptl_crystal_size_mid          0.196
_exptl_crystal_size_min          0.078
_exptl_absorpt_coefficient_mu    2.616
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5695
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microfocus
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26273
_diffrn_reflns_av_unetI/netI     0.0385
_diffrn_reflns_av_R_equivalents  0.0638
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.404
_diffrn_reflns_theta_max         30.592
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.966
_reflns_number_total             3717
_reflns_number_gt                3354
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'XT, VERSION 2014/5'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0459P)²+1.1655P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3717
_refine_ls_number_parameters     189
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0394
_refine_ls_R_factor_gt           0.0352
_refine_ls_wR_factor_ref         0.0956
_refine_ls_wR_factor_gt          0.0908
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.080
_refine_ls_shift/su_max          0.001
_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
I1 I 0.32822(2) -0.16735(4) 0.32255(2) 0.03989(9) Uani 1 1 d . . . . .
F1 F 0.5423(2) 0.5734(14) 0.45396(19) 0.0590(10) Uani 0.5 1 d . . P A 1
F1' F 0.7198(3) 0.2404(18) 0.2820(3) 0.0779(15) Uani 0.5 1 d . . P B 2
F2 F 0.80907(19) 0.6831(9) 0.50545(17) 0.0953(11) Uani 1 1 d . . . . .
O1 O 0.44712(14) 0.2963(7) 0.05697(10) 0.0514(6) Uani 1 1 d . . . . .
O2 O 0.55964(14) 0.5581(8) 0.08701(11) 0.0553(6) Uani 1 1 d . . . . .
H2O H 0.557(4) 0.585(16) 0.050(3) 0.088(18) Uiso 1 1 d . . . . .
O3 O 0.36828(13) 0.0320(7) 0.16242(11) 0.0470(5) Uani 1 1 d . . . . .
H3O H 0.380(3) 0.084(11) 0.124(2) 0.051(10) Uiso 1 1 d . . . . .
C1 C 0.49871(16) 0.3822(8) 0.10381(13) 0.0381(5) Uani 1 1 d . . . . .
C2 C 0.49631(15) 0.2942(7) 0.18298(12) 0.0329(5) Uani 1 1 d . . . . .
C3 C 0.42984(15) 0.1287(6) 0.20736(13) 0.0331(5) Uani 1 1 d . . . . .
C4 C 0.42797(14) 0.0597(6) 0.28363(12) 0.0313(4) Uani 1 1 d . . . . .
C5 C 0.49009(16) 0.1477(6) 0.33236(13) 0.0327(5) Uani 1 1 d . . . . .
H5 H 0.487577 0.098993 0.382536 0.039 Uiso 1 1 calc R U . . .
C6 C 0.55703(15) 0.3090(6) 0.30798(12) 0.0317(4) Uani 1 1 d . . . . .
C7 C 0.55867(15) 0.3828(7) 0.23298(12) 0.0333(5) Uani 1 1 d . . . . .
H7 H 0.602024 0.493183 0.215738 0.040 Uiso 1 1 calc R U . . .
C8 C 0.62347(15) 0.4042(7) 0.36088(12) 0.0338(5) Uani 1 1 d . . . . .
C9 C 0.61132(19) 0.5345(8) 0.43058(13) 0.0437(6) Uani 1 1 d . . . . .
H9 H 0.559839 0.559457 0.444656 0.052 Uiso 0.5 1 calc R U P A 2
C10 C 0.6733(3) 0.6293(9) 0.48021(16) 0.0566(9) Uani 1 1 d . . . . .
H10 H 0.663897 0.716017 0.526599 0.068 Uiso 1 1 calc R U . . .
C11 C 0.7482(2) 0.5905(10) 0.45833(19) 0.0581(9) Uani 1 1 d . . . . .
C13 C 0.70114(18) 0.3695(9) 0.34360(16) 0.0464(6) Uani 1 1 d . . . . .
H13 H 0.711517 0.278252 0.297880 0.056 Uiso 0.5 1 calc R U P B 1
C12 C 0.7646(2) 0.4640(12) 0.3910(2) 0.0597(9) Uani 1 1 d . . . . .
H12 H 0.816272 0.441664 0.377349 0.072 Uiso 1 1 calc R U . . .


_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
I1 C4 2.084(2) . ?
F1 C9 1.278(5) . ?
F1' C13 1.285(5) . ?
F2 C11 1.351(4) . ?
O1 C1 1.231(3) . ?
O2 C1 1.306(4) . ?
O2 H2O 0.67(6) . ?
O3 C3 1.342(3) . ?
O3 H3O 0.76(4) . ?
C1 C2 1.475(3) . ?
C2 C7 1.396(3) . ?
C2 C3 1.405(4) . ?
C3 C4 1.406(3) . ?
C4 C5 1.379(3) . ?
C5 C6 1.404(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.388(3) . ?
C6 C8 1.484(3) . ?
C7 H7 0.9300 . ?
C8 C13 1.380(4) . ?
C8 C9 1.390(3) . ?
C9 C10 1.395(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.363(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.361(6) . ?
C13 C12 1.389(4) . ?
C13 H13 0.9300 . ?
C12 H12 0.9300 . ?

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
C1 O2 H2O 108(5) . . ?
C3 O3 H3O 104(3) . . ?
O1 C1 O2 122.4(2) . . ?
O1 C1 C2 122.5(3) . . ?
O2 C1 C2 115.1(2) . . ?
C7 C2 C3 120.8(2) . . ?
C7 C2 C1 120.0(2) . . ?
C3 C2 C1 119.2(2) . . ?
O3 C3 C2 124.1(2) . . ?
O3 C3 C4 118.1(2) . . ?
C2 C3 C4 117.8(2) . . ?
C5 C4 C3 120.8(2) . . ?
C5 C4 I1 120.31(17) . . ?
C3 C4 I1 118.89(18) . . ?
C4 C5 C6 121.5(2) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C7 C6 C5 118.0(2) . . ?
C7 C6 C8 120.9(2) . . ?
C5 C6 C8 121.2(2) . . ?
C6 C7 C2 121.1(2) . . ?
C6 C7 H7 119.4 . . ?
C2 C7 H7 119.4 . . ?
C13 C8 C9 116.0(2) . . ?
C13 C8 C6 121.9(2) . . ?
C9 C8 C6 122.1(2) . . ?
F1 C9 C8 122.2(3) . . ?
F1 C9 C10 115.2(3) . . ?
C8 C9 C10 122.6(3) . . ?
C8 C9 H9 118.7 . . ?
C10 C9 H9 118.7 . . ?
C11 C10 C9 117.7(3) . . ?
C11 C10 H10 121.2 . . ?
C9 C10 H10 121.2 . . ?
F2 C11 C12 118.5(4) . . ?
F2 C11 C10 118.5(4) . . ?
C12 C11 C10 123.0(3) . . ?
F1' C13 C8 121.7(3) . . ?
F1' C13 C12 115.0(4) . . ?
C8 C13 C12 123.3(3) . . ?
C8 C13 H13 118.3 . . ?
C12 C13 H13 118.3 . . ?
C11 C12 C13 117.5(3) . . ?
C11 C12 H12 121.3 . . ?
C13 C12 H12 121.3 . . ?

_refine_diff_density_max         1.014
_refine_diff_density_min         -1.418
_refine_diff_density_rms         0.111

