# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1862413'
_audit_update_record             
;
2018-08-16 deposited with the CCDC.
2018-09-28 downloaded from the CCDC.
;




##############################################################################
### VALIDATION RESPONSE FORM (VRF)                                         ###
###                                                                        ###
### AUTHOR: PLEASE INSERT THE BLOCK OF TEXT FROM HERE TO THE END OF THE    ###
### VRF IN YOUR CIF AND ADD YOUR RESPONSE(S) IN THE APPROPRIATE PLACE(S).  ###
### THE BLOCK SHOULD BE INSERTED IN THE CIF AFTER THE FIRST DATABLOCK      ###
### IDENTIFIER.                                                            ###
###                                                                        ###
##############################################################################
_vrf_PLAT430_1                   
;
PROBLEM: Short Inter D...A Contact  O1       ..O1               2.79 Ang.  
RESPONSE: short contact related to halogen bond, see article.
;
_vrf_PLAT431_1                   
;
PROBLEM: Short Inter HL..A Contact  I1       ..O1               2.98 Ang.  
RESPONSE: short contact related to halogen bond, see article.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            'compound 1, Togni reagent I'
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H10 F3 I O'
_chemical_formula_sum            'C10 H10 F3 I O'
_chemical_formula_weight         330.08

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           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                   9.1507(5)
_cell_length_b                   9.0836(5)
_cell_length_c                   13.3668(7)
_cell_angle_alpha                90
_cell_angle_beta                 93.2446(16)
_cell_angle_gamma                90
_cell_volume                     1109.28(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    19792
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      52.80

_exptl_crystal_description       'translucent block'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.976
_exptl_crystal_F_000             632
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    2.899
_shelx_estimated_absorpt_T_min   0.422
_shelx_estimated_absorpt_T_max   0.780
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.322
_exptl_absorpt_correction_T_max  0.579
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Incoatec microsource'
_diffrn_radiation_monochromator  'multilayer optics'
_diffrn_measurement_device_type  'Bruker D8 gonimeter with APEX CCD detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            151509
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_av_R_equivalents  0.0530
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.630
_diffrn_reflns_theta_max         51.430
_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 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             12366
_reflns_number_gt                10687
_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       'SMART (Bruker, 2002)'
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_structure_solution    'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0230P)²+0.1700P] 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         12366
_refine_ls_number_parameters     138
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0271
_refine_ls_R_factor_gt           0.0221
_refine_ls_wR_factor_ref         0.0552
_refine_ls_wR_factor_gt          0.0534
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.084
_refine_ls_shift/su_max          0.006
_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 0.59578(2) 0.53298(2) 0.35605(2) 0.01417(1) Uani 1 1 d . . . . .
F1 F 0.89002(8) 0.44989(10) 0.30358(6) 0.03181(14) Uani 1 1 d . . . . .
F2 F 0.81859(8) 0.62299(8) 0.20120(5) 0.03017(13) Uani 1 1 d . . . . .
F3 F 0.74727(8) 0.39939(8) 0.17395(5) 0.02921(12) Uani 1 1 d . . . . .
O1 O 0.40862(7) 0.58529(7) 0.43612(4) 0.01931(9) Uani 1 1 d . . . . .
C1 C 0.77438(10) 0.50003(11) 0.24671(6) 0.02105(12) Uani 1 1 d . . . . .
C2 C 0.32553(9) 0.70305(10) 0.39321(6) 0.01970(11) Uani 1 1 d . . . . .
C3 C 0.38690(14) 0.85171(12) 0.43152(8) 0.02964(18) Uani 1 1 d . . . . .
H3A H 0.383581 0.855749 0.504624 0.044 Uiso 1 1 calc R U . . .
H3B H 0.327781 0.931919 0.401467 0.044 Uiso 1 1 calc R U . . .
H3C H 0.488431 0.862111 0.412876 0.044 Uiso 1 1 calc R U . . .
C4 C 0.16804(11) 0.68175(16) 0.42259(8) 0.0313(2) Uani 1 1 d . . . . .
H4A H 0.132308 0.585363 0.399116 0.047 Uiso 1 1 calc R U . . .
H4B H 0.106051 0.759309 0.391862 0.047 Uiso 1 1 calc R U . . .
H4C H 0.164696 0.686927 0.495661 0.047 Uiso 1 1 calc R U . . .
C5 C 0.33671(9) 0.69645(9) 0.27963(5) 0.01866(11) Uani 1 1 d . . . . .
C6 C 0.23537(12) 0.76200(12) 0.21141(7) 0.02626(16) Uani 1 1 d . . . . .
H6 H 0.153190 0.812154 0.235337 0.032 Uiso 1 1 calc R U . . .
C7 C 0.25321(13) 0.75480(12) 0.10900(7) 0.02736(16) Uani 1 1 d . . . . .
H7 H 0.182711 0.798877 0.063466 0.033 Uiso 1 1 calc R U . . .
C8 C 0.37345(11) 0.68357(11) 0.07303(6) 0.02336(14) Uani 1 1 d . . . . .
H8 H 0.385196 0.679319 0.002924 0.028 Uiso 1 1 calc R U . . .
C9 C 0.47730(9) 0.61809(9) 0.13924(5) 0.01940(11) Uani 1 1 d . . . . .
H9 H 0.560274 0.569236 0.115381 0.023 Uiso 1 1 calc R U . . .
C10 C 0.45578(8) 0.62646(8) 0.24115(5) 0.01605(9) 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
I1 C10 2.1208(7) . ?
I1 O1 2.1241(6) . ?
I1 C1 2.2731(8) . ?
F1 C1 1.3468(12) . ?
F2 C1 1.3450(12) . ?
F3 C1 1.3475(12) . ?
O1 C2 1.4149(10) . ?
C2 C4 1.5273(13) . ?
C2 C5 1.5285(11) . ?
C2 C3 1.5390(15) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C10 1.3854(10) . ?
C5 C6 1.3966(12) . ?
C6 C7 1.3892(13) . ?
C6 H6 0.9500 . ?
C7 C8 1.3859(15) . ?
C7 H7 0.9500 . ?
C8 C9 1.3946(12) . ?
C8 H8 0.9500 . ?
C9 C10 1.3895(9) . ?
C9 H9 0.9500 . ?

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
C10 I1 O1 78.70(2) . . ?
C10 I1 C1 90.80(3) . . ?
O1 I1 C1 169.41(3) . . ?
C2 O1 I1 113.26(4) . . ?
F2 C1 F1 106.81(8) . . ?
F2 C1 F3 106.54(7) . . ?
F1 C1 F3 106.54(8) . . ?
F2 C1 I1 115.28(6) . . ?
F1 C1 I1 104.61(6) . . ?
F3 C1 I1 116.34(6) . . ?
O1 C2 C4 107.05(7) . . ?
O1 C2 C5 107.96(6) . . ?
C4 C2 C5 111.57(8) . . ?
O1 C2 C3 110.54(8) . . ?
C4 C2 C3 110.94(8) . . ?
C5 C2 C3 108.74(7) . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C2 C4 H4A 109.5 . . ?
C2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C10 C5 C6 117.41(7) . . ?
C10 C5 C2 119.01(7) . . ?
C6 C5 C2 123.54(7) . . ?
C7 C6 C5 120.84(9) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C8 C7 C6 120.25(8) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C7 C8 C9 120.32(7) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C10 C9 C8 118.00(8) . . ?
C10 C9 H9 121.0 . . ?
C8 C9 H9 121.0 . . ?
C5 C10 C9 123.18(7) . . ?
C5 C10 I1 111.74(5) . . ?
C9 C10 I1 125.08(6) . . ?

_refine_diff_density_max         1.593
_refine_diff_density_min         -0.771
_refine_diff_density_rms         0.138

####################################################################### 
# 
# 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_mm
_database_code_depnum_ccdc_archive 'CCDC 1862414'
_audit_update_record             
;
2018-08-16 deposited with the CCDC.
2018-09-28 downloaded from the CCDC.
;

##############################################################################
_vrf_PLAT430_1                   
;
PROBLEM: Short Inter D...A Contact  O1       ..O1               2.79 Ang.
RESPONSE: short contact related to halogen bond, see article.
;
_vrf_PLAT431_1                   
;
PROBLEM: Short Inter HL..A Contact  I1       ..O1               2.98 Ang.
RESPONSE: short contact related to halogen bond, see article.
;
###############################################################################

_audit_creation_date             '14-Aug-08 T13:19:25-00:00'
_audit_creation_method           'XD routine XDCIF'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#
_chemical_name_systematic        ?
_chemical_name_common            'compound 1, Togni reagent I'
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H10 F3 I O'
_chemical_formula_sum            'C10 H10 F3 I O'
_chemical_formula_weight         330.08

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


#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 1/2+X,1/2-Y,1/2+Z

_cell_length_a                   9.1507(5)
_cell_length_b                   9.0836(5)
_cell_length_c                   13.3668(7)
_cell_angle_alpha                90
_cell_angle_beta                 93.2446(16)
_cell_angle_gamma                90
_cell_volume                     1109.28(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    19792
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      52.80

#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#
_exptl_crystal_description       'translucent block'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.976
_exptl_crystal_F_000             632
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.090

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#
_exptl_absorpt_coefficient_mu    2.899
_shelx_estimated_absorpt_T_min   0.422
_shelx_estimated_absorpt_T_max   0.780
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.322
_exptl_absorpt_correction_T_max  0.579
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_special_details   ?
#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Incoatec microsource'
_diffrn_radiation_monochromator  'multilayer optics'
_diffrn_measurement_device_type  'Bruker D8 gonimeter with APEX CCD detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            151509
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_av_R_equivalents  0.0530
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.630
_diffrn_reflns_theta_max         51.430
_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 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_structure_solution    'SHELXS-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'Volkov et al, (2006)'
_computing_molecular_graphics    'Volkov et al, (2006)'
_computing_publication_material  'Volkov et al, (2006)'

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
        ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;    calc w2 = q/[s²(Fo²) + (0.03 P)² + 0.14 P + 0.00 + 0.00 sin(th)]
     where P = (0.3333 Fo² + 0.6667 Fc²)
           q = 1.0
;
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         12366
_reflns_number_gt                10687
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_number_parameters     543
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.034
_refine_ls_R_factor_gt           0.019
_refine_ls_wR_factor_ref         0.050
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_shift/su_max          0.0001

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_symmetry_multiplicity
I(1) 0.595768(4) 0.532982(4) 0.356044(3) 0.014 1 4
F(1) 0.88994(17) 0.4488(3) 0.30372(13) 0.031 1 4
F(2) 0.8187(2) 0.6230(2) 0.20114(12) 0.03 1 4
F(3) 0.7472(2) 0.3995(2) 0.17368(11) 0.029 1 4
O(1) 0.40865(12) 0.58560(14) 0.43607(7) 0.019 1 4
C(1) 0.77466(9) 0.50009(11) 0.24668(6) 0.021 1 4
C(2) 0.32560(9) 0.70305(9) 0.39322(5) 0.02 1 4
C(3) 0.38762(17) 0.85183(13) 0.43162(8) 0.03 1 4
C(4) 0.16844(13) 0.68253(19) 0.42262(9) 0.031 1 4
C(5) 0.33670(9) 0.69646(9) 0.27975(5) 0.019 1 4
C(6) 0.23505(12) 0.76211(12) 0.21155(7) 0.027 1 4
C(7) 0.25286(13) 0.75499(13) 0.10881(7) 0.027 1 4
C(8) 0.37352(11) 0.68347(11) 0.07292(6) 0.023 1 4
C(9) 0.47744(9) 0.61802(9) 0.13922(5) 0.019 1 4
C(10) 0.45582(8) 0.62644(8) 0.24122(5) 0.016 1 4
H(3A) 0.384307 0.855949 0.51296 0.044 1 4
H(3B) 0.320946 0.940717 0.398635 0.044 1 4
H(3C) 0.500204 0.863697 0.410223 0.044 1 4
H(4A) 0.128393 0.575448 0.39647 0.047 1 4
H(4B) 0.099059 0.768432 0.388416 0.047 1 4
H(4C) 0.164474 0.687486 0.503899 0.047 1 4
H(6) 0.136759 0.815438 0.236434 0.034 1 4
H(7) 0.16913 0.801802 0.056959 0.035 1 4
H(8) 0.383647 0.674033 -0.007688 0.037 1 4
H(9) 0.571728 0.565663 0.107801 0.03 1 4


#----------------------------------------------------------------------------#
#                   MULTIPOLE PARAMETERS                                     #
#----------------------------------------------------------------------------#

loop_
_atom_rho_multipole_atom_label
_atom_rho_multipole_coeff_Pv
_atom_rho_multipole_coeff_P00
_atom_rho_multipole_coeff_P11
_atom_rho_multipole_coeff_P1-1
_atom_rho_multipole_coeff_P10
_atom_rho_multipole_coeff_P20
_atom_rho_multipole_coeff_P21
_atom_rho_multipole_coeff_P2-1
_atom_rho_multipole_coeff_P22
_atom_rho_multipole_coeff_P2-2
_atom_rho_multipole_coeff_P30
_atom_rho_multipole_coeff_P31
_atom_rho_multipole_coeff_P3-1
_atom_rho_multipole_coeff_P32
_atom_rho_multipole_coeff_P3-2
_atom_rho_multipole_coeff_P33
_atom_rho_multipole_coeff_P3-3
_atom_rho_multipole_coeff_P40
_atom_rho_multipole_coeff_P41
_atom_rho_multipole_coeff_P4-1
_atom_rho_multipole_coeff_P42
_atom_rho_multipole_coeff_P4-2
_atom_rho_multipole_coeff_P43
_atom_rho_multipole_coeff_P4-3
_atom_rho_multipole_coeff_P44
_atom_rho_multipole_coeff_P4-4
_atom_rho_multipole_kappa
_atom_rho_multipole_kappa_prime0
_atom_rho_multipole_kappa_prime1
_atom_rho_multipole_kappa_prime2
_atom_rho_multipole_kappa_prime3
_atom_rho_multipole_kappa_prime4
_atom_rho_multipole_radial_slater_n0
_atom_rho_multipole_radial_slater_zeta0
_atom_rho_multipole_radial_slater_n1
_atom_rho_multipole_radial_slater_zeta1
_atom_rho_multipole_radial_slater_n2
_atom_rho_multipole_radial_slater_zeta2
_atom_rho_multipole_radial_slater_n3
_atom_rho_multipole_radial_slater_zeta3
_atom_rho_multipole_radial_slater_n4
_atom_rho_multipole_radial_slater_zeta4
I(1) 6.04(17) 0 -0.03(3) -0.03(2) -0.11(2) -0.01(3) 0.04(3) 0.47(3) -0.01(3)
0.23(2) 0.01(2) -0.037(19) 0.045(18) -0.017(19) 0.008(19) 0.065(19) -0.027(18)
-0.03(2) -0.29(3) 0.26(2) -0.05(2) 0.06(3) 0.06(2) 0.05(2) 0.12(2) -0.05(2)
1.203(12) 1.5 1.5 1.5 1.5 1.5 8 4.8152571428571 8 4.8152571428571 8
4.8152571428571 8 4.8152571428571 8 4.8152571428571
F(1) 7.18(8) 0 0.11(4) -0.13(4) 0.05(4) -0.06(4) 0.01(4) 0.02(4) -0.05(4)
-0.08(4) -0.05(3) 0.03(3) -0.01(3) 0.00(3) -0.13(3) 0.04(3) -0.01(3) 0.03(3)
0.03(3) -0.02(3) 0.01(3) -0.06(3) -0.02(3) 0.01(3) 0.03(3) 0.00(3) 0.971(5)
1.03(7) 1.030021 1.030021 1.030021 1.030021 2 5.186 2 5.186 2 5.186 3 5.186 4
5.186
F(2) 7.25(8) 0 0.03(4) 0.00(4) 0.01(3) -0.08(4) -0.02(4) 0.01(4) 0.03(4)
0.02(4) -0.04(3) 0.01(2) -0.01(2) -0.08(2) 0.02(2) 0.04(2) -0.01(2) 0.00(3)
-0.02(3) -0.05(3) 0.00(3) 0.03(3) -0.12(3) -0.02(3) 0.05(3) 0.00(3) 0.971(5)
1.03(7) 1.030021 1.030021 1.030021 1.030021 2 5.186 2 5.186 2 5.186 3 5.186 4
5.186
F(3) 7.29(8) 0 0.06(4) -0.09(4) 0.01(3) -0.10(4) 0.05(4) 0.08(4) -0.01(4)
0.00(4) -0.02(3) 0.05(2) -0.02(2) -0.04(2) -0.16(2) 0.02(2) -0.09(2) 0.07(3)
-0.01(3) -0.07(3) -0.02(3) -0.02(3) 0.01(3) 0.00(3) 0.05(3) -0.02(3) 0.971(5)
1.03(7) 1.030021 1.030021 1.030021 1.030021 2 5.186 2 5.186 2 5.186 3 5.186 4
5.186
O(1) 6.36(12) 0 -0.01(3) -0.04(2) -0.08(2) -0.13(3) -0.05(3) 0.03(2) 0.10(3)
0.08(2) 0.061(19) -0.017(19) -0.032(17) 0.014(18) 0.007(18) -0.005(18)
0.020(18) 0.07(2) -0.06(2) 0.03(2) -0.02(2) -0.02(2) 0.02(2) -0.05(2) 0.03(2)
0.02(2) 0.973(7) 1.18(11) 1.183319 1.183319 1.183319 1.183319 2 4.4974 2 4.4974
2 4.4974 3 4.4974 4 4.4974
C(1) 4.4(2) 0 -0.13(5) -0.13(5) -0.08(5) -0.01(5) 0.02(4) 0.14(4) -0.02(4)
0.12(4) 0.49(8) -0.05(5) -0.16(6) 0.16(5) 0.04(5) 0.12(5) -0.33(6) 0.23(8)
0.06(7) -0.04(7) -0.08(7) -0.11(7) -0.03(6) 0.20(7) -0.10(6) -0.01(6) 0.923(17)
0.83(4) 0.832164 0.832164 0.832164 0.832164 2 3.1303 2 3.1303 2 3.1303 3 3.1303
4 3.1303
C(2) 4.6(3) 0 -0.21(11) 0.01(10) 0.02(9) -0.12(7) 0.04(7) 0.04(7) -0.20(7)
0.01(7) 0.78(14) 0.10(9) -0.26(8) 0.21(9) -0.28(9) 0.08(9) -0.51(11) 0.24(12)
-0.19(11) 0.22(10) -0.33(11) 0.51(11) 0.02(11) 0.46(13) -0.14(11) 0.20(12)
0.93(2) 0.71(3) 0.712064 0.712064 0.712064 0.712064 2 3.1303 2 3.1303 2 3.1303
3 3.1303 4 3.1303
C(3) 5.0(3) 0 -0.01(6) -0.15(7) 0.22(7) -0.09(6) -0.04(5) -0.01(5) -0.13(6)
0.01(5) 0.21(7) 0.05(5) 0.19(5) -0.07(5) 0.00(5) 0.09(5) -0.17(6) 0.22(8)
0.02(6) -0.10(6) 0.03(6) 0.01(6) 0.06(6) 0.04(7) -0.03(6) -0.16(6) 0.926(16)
0.89(5) 0.89233 0.89233 0.89233 0.89233 2 3.1303 2 3.1303 2 3.1303 3 3.1303 4
3.1303
C(4) 4.3(3) 0 0.08(6) 0.31(8) 0.04(7) -0.05(6) -0.16(5) -0.16(5) -0.13(6)
0.02(6) 0.36(8) -0.01(5) -0.11(5) 0.20(6) -0.09(6) -0.02(5) -0.39(8) -0.06(7)
0.07(6) 0.16(7) -0.07(6) 0.03(6) 0.04(6) 0.16(7) 0.16(7) 0.00(6) 0.926(16)
0.89(5) 0.89233 0.89233 0.89233 0.89233 2 3.1303 2 3.1303 2 3.1303 3 3.1303 4
3.1303
C(5) 3.4(2) 0 0.23(11) 0.14(13) 0.33(13) 0.19(8) -0.06(7) -0.06(8) -0.12(7)
0.05(7) 0.18(10) 0.14(8) -0.05(10) 0.16(9) 0.12(9) -0.24(8) 0.02(8) 0.24(13)
0.00(10) 0.22(13) -0.05(11) 0.02(12) -0.09(9) -0.02(10) 0.09(9) 0.07(8)
0.956(6) 0.752(18) 0.751923 0.751923 0.751923 0.751923 2 3.1303 2 3.1303 2
3.1303 3 3.1303 4 3.1303
C(6) 4.1(2) 0 0.00(10) -0.23(14) -0.06(12) 0.32(9) 0.06(7) 0.00(9) -0.29(9)
0.06(9) 0.43(10) 0.00(7) 0.17(10) 0.44(9) 0.18(9) -0.01(9) 0.17(10) -0.19(11)
-0.03(9) -0.08(11) -0.05(9) -0.15(10) -0.08(9) -0.32(10) -0.01(10) -0.29(9)
0.956(6) 0.752(18) 0.751923 0.751923 0.751923 0.751923 2 3.1303 2 3.1303 2
3.1303 3 3.1303 4 3.1303
C(7) 4.4(2) 0 0.07(11) 0.18(15) -0.08(13) 0.10(9) 0.02(7) 0.17(9) -0.39(9)
0.02(9) 0.56(11) -0.04(8) -0.30(11) 0.46(10) 0.22(10) -0.16(9) -0.04(10)
-0.09(12) -0.11(9) 0.29(12) 0.05(10) -0.12(10) 0.10(10) -0.06(10) 0.12(10)
-0.25(10) 0.956(6) 0.752(18) 0.751923 0.751923 0.751923 0.751923 2 3.1303 2
3.1303 2 3.1303 3 3.1303 4 3.1303
C(8) 3.8(2) 0 -0.08(10) 0.07(15) 0.19(12) 0.25(8) 0.22(7) -0.01(9) -0.36(9)
0.07(8) 0.42(10) -0.04(7) -0.24(11) 0.17(10) 0.04(9) -0.04(8) 0.04(10) 0.22(11)
-0.16(9) 0.04(11) 0.09(10) -0.07(10) -0.01(10) 0.03(11) 0.28(9) 0.02(9)
0.956(6) 0.752(18) 0.751923 0.751923 0.751923 0.751923 2 3.1303 2 3.1303 2
3.1303 3 3.1303 4 3.1303
C(9) 4.1(2) 0 0.00(9) -0.14(13) -0.05(11) 0.34(8) -0.05(6) 0.12(8) -0.24(7)
0.10(7) 0.43(9) 0.10(7) 0.30(10) 0.33(8) -0.15(9) 0.01(8) 0.02(9) 0.05(11)
-0.13(8) -0.33(11) -0.01(9) 0.08(9) 0.03(9) 0.03(9) 0.07(9) 0.20(8) 0.956(6)
0.752(18) 0.751923 0.751923 0.751923 0.751923 2 3.1303 2 3.1303 2 3.1303 3
3.1303 4 3.1303
C(10) 4.3(2) 0 0.06(9) -0.04(11) -0.07(12) 0.28(8) 0.05(6) -0.19(7) -0.07(6)
0.05(6) 0.40(10) 0.08(8) 0.16(9) 0.18(8) 0.07(8) 0.17(6) -0.01(6) -0.17(11)
0.12(9) -0.03(10) -0.21(9) 0.08(9) -0.23(8) -0.11(9) -0.19(7) -0.19(7) 0.956(6)
0.752(18) 0.751923 0.751923 0.751923 0.751923 2 3.1303 2 3.1303 2 3.1303 3
3.1303 4 3.1303
H(3A) 0.73(8) 0 0 0 0.07(5) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 1.9154 1 1.9154 2 1.9154 3 1.9154 4 1.9154
H(3B) 0.86(9) 0 0 0 0.12(6) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 1.9154 1 1.9154 2 1.9154 3 1.9154 4 1.9154
H(3C) 0.91(9) 0 0 0 0.09(5) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 1.9154 1 1.9154 2 1.9154 3 1.9154 4 1.9154
H(4A) 0.49(10) 0 0 0 0.02(6) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 1.9154 1 1.9154 2 1.9154 3 1.9154 4 1.9154
H(4B) 0.70(10) 0 0 0 0.16(6) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 1.9154 1 1.9154 2 1.9154 3 1.9154 4 1.9154
H(4C) 1.02(9) 0 0 0 0.22(5) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 1.9154 1 1.9154 2 1.9154 3 1.9154 4 1.9154
H(6) 0.71(8) 0 0 0 0.18(5) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 1.9154 1 1.9154 2 1.9154 3 1.9154 4 1.9154
H(7) 0.75(8) 0 0 0 0.23(5) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 1.9154 1 1.9154 2 1.9154 3 1.9154 4 1.9154
H(8) 0.59(8) 0 0 0 0.23(5) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 1.9154 1 1.9154 2 1.9154 3 1.9154 4 1.9154
H(9) 0.67(7) 0 0 0 0.14(4) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 1.9154 1 1.9154 2 1.9154 3 1.9154 4 1.9154

loop_
_atom_local_axes_atom_label
_atom_local_axes_atom0
_atom_local_axes_ax1
_atom_local_axes_atom1
_atom_local_axes_atom2
_atom_local_axes_ax2
I(1) C(10) Z I(1) O(1) Y
F(1) C(1) Z F(1) F(3) Y
F(2) C(1) Z F(2) F(3) Y
F(3) C(1) Z F(3) F(2) Y
O(1) C(2) Z O(1) I(1) Y
C(1) F(1) Z C(1) F(2) Y
C(2) O(1) Z C(2) C(4) Y
C(3) H(3B) Z C(3) H(3C) Y
C(4) H(4C) Z C(4) H(4A) Y
C(5) C(10) Z C(5) C(6) Y
C(6) H(6) Z C(6) C(7) Y
C(7) H(7) Z C(7) C(6) Y
C(8) H(8) Z C(8) C(7) Y
C(9) H(9) Z C(9) C(10) Y
C(10) C(5) Z C(10) C(9) Y
H(3A) C(3) Z H(3A) H(3B) Y
H(3B) C(3) Z H(3B) H(3C) Y
H(3C) C(3) Z H(3C) H(3B) Y
H(4A) C(4) Z H(4A) H(4C) Y
H(4B) C(4) Z H(4B) H(4C) Y
H(4C) C(4) Z H(4C) H(4A) Y
H(6) C(6) Z H(6) C(7) Y
H(7) C(7) Z H(7) C(6) Y
H(8) C(8) Z H(8) C(7) Y
H(9) C(9) Z H(9) C(10) Y

#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F(1) C(1) 1.3492(18) 1_555 1_555 yes
F(2) C(1) 1.3445(18) 1_555 1_555 yes
F(3) C(1) 1.3498(17) 1_555 1_555 yes
O(1) C(2) 1.4124(14) 1_555 1_555 yes
C(2) C(4) 1.5236(14) 1_555 1_555 yes
C(2) C(5) 1.5269(10) 1_555 1_555 yes
C(5) C(6) 1.3986(11) 1_555 1_555 yes
C(5) C(10) 1.3862(10) 1_555 1_555 yes
C(6) C(7) 1.3935(13) 1_555 1_555 yes
C(7) C(8) 1.3898(15) 1_555 1_555 yes
C(8) C(9) 1.3956(12) 1_555 1_555 yes
C(9) C(10) 1.3908(9) 1_555 1_555 yes

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F(1) C(1) F(2) 107.34(14) 1_555 1_555 1_555 yes
F(1) C(1) F(3) 106.41(13) 1_555 1_555 1_555 yes
F(2) C(1) F(3) 106.45(12) 1_555 1_555 1_555 yes
O(1) C(2) C(4) 107.28(9) 1_555 1_555 1_555 yes
O(1) C(2) C(5) 107.99(7) 1_555 1_555 1_555 yes
C(4) C(2) C(5) 111.61(8) 1_555 1_555 1_555 yes
C(2) C(5) C(6) 123.48(7) 1_555 1_555 1_555 yes
C(2) C(5) C(10) 119.01(6) 1_555 1_555 1_555 yes
C(6) C(5) C(10) 117.48(7) 1_555 1_555 1_555 yes
C(5) C(6) C(7) 120.80(9) 1_555 1_555 1_555 yes
C(6) C(7) C(8) 120.09(9) 1_555 1_555 1_555 yes
C(7) C(8) C(9) 120.40(7) 1_555 1_555 1_555 yes
C(8) C(9) C(10) 118.00(8) 1_555 1_555 1_555 yes
C(5) C(10) C(9) 123.23(7) 1_555 1_555 1_555 yes

_refine_diff_density_max         0.895
_refine_diff_density_min         -0.889
_refine_diff_density_rms         0.122

