# Supplementary Information (SI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_C4-I12
_database_code_depnum_ccdc_archive 'CCDC 2281927'
loop_
_audit_author_name
_audit_author_address
'Weizhou Wang'
;Luoyang Normal University
China
;
_audit_update_record             
;
2023-07-17 deposited with the CCDC.	2024-09-11 downloaded from the CCDC.
;



_audit_creation_method           SHELXL-97

_chemical_name_systematic        
;

 ?

;

_chemical_name_common            ?

_chemical_melting_point          ?

_chemical_formula_moiety         ?

_chemical_formula_sum            'C20 H16 F8 I4 O4'

_chemical_formula_weight         979.93



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'



_symmetry_cell_setting           Triclinic

_symmetry_space_group_name_H-M   P-1



loop_

_symmetry_equiv_pos_as_xyz


'x, y, z'
'-x, -y, -z'



_cell_length_a                   8.1008(7)

_cell_length_b                   8.2512(6)

_cell_length_c                   10.7542(8)

_cell_angle_alpha                76.846(6)

_cell_angle_beta                 78.005(7)

_cell_angle_gamma                89.406(6)

_cell_volume                     684.17(9)

_cell_formula_units_Z            1

_cell_measurement_temperature    295(2)

_cell_measurement_reflns_used    1473

_cell_measurement_theta_min      3.5430

_cell_measurement_theta_max      24.6110



_exptl_crystal_description       block

_exptl_crystal_colour            colourless

_exptl_crystal_size_max          0.30

_exptl_crystal_size_mid          0.30

_exptl_crystal_size_min          0.10

_exptl_crystal_density_meas      ?

_exptl_crystal_density_diffrn    2.378

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             452

_exptl_absorpt_coefficient_mu    4.634

_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.3370

_exptl_absorpt_correction_T_max  0.6544

_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;



_exptl_special_details           
;

 ?

;



_diffrn_ambient_temperature      295(2)

_diffrn_radiation_wavelength     0.71073

_diffrn_radiation_type           MoK\a

_diffrn_radiation_source         'Enhance (Mo) X-ray Source'

_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'

_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 16.2542

_diffrn_standards_number         ?

_diffrn_standards_interval_count ?

_diffrn_standards_interval_time  ?

_diffrn_standards_decay_%        ?

_diffrn_reflns_number            4527

_diffrn_reflns_av_R_equivalents  0.0258

_diffrn_reflns_av_sigmaI/netI    0.0442

_diffrn_reflns_limit_h_min       -9

_diffrn_reflns_limit_h_max       9

_diffrn_reflns_limit_k_min       -9

_diffrn_reflns_limit_k_max       9

_diffrn_reflns_limit_l_min       -13

_diffrn_reflns_limit_l_max       13

_diffrn_reflns_theta_min         2.90

_diffrn_reflns_theta_max         25.49

_reflns_number_total             2524

_reflns_number_gt                1992

_reflns_threshold_expression     >2sigma(I)



_computing_data_collection       'Bruker FRAMBO'

_computing_cell_refinement       'Bruker FRAMBO'

_computing_data_reduction        'Bruker SAINT'

_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

_computing_molecular_graphics    'Bruker SHELXTL'

_computing_publication_material  'Bruker SHELXTL'



_refine_special_details          
;

 Refinement of F² against ALL reflections.  The weighted R-factor wR and

 goodness of fit S are based on F², conventional R-factors R are based

 on F, with F set to zero for negative F². The threshold expression of

 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is

 not relevant to the choice of reflections for refinement.  R-factors based

 on F² are statistically about twice as large as those based on F, and R-

 factors based on ALL data will be even larger.

;



_refine_ls_structure_factor_coef Fsqd

_refine_ls_matrix_type           full

_refine_ls_weighting_scheme      calc

_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0271P)²+0.0000P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_primary     direct

_atom_sites_solution_secondary   difmap

_atom_sites_solution_hydrogens   geom

_refine_ls_hydrogen_treatment    constr

_refine_ls_extinction_method     none

_refine_ls_extinction_coef       ?

_refine_ls_number_reflns         2524

_refine_ls_number_parameters     163

_refine_ls_number_restraints     0

_refine_ls_R_factor_all          0.0534

_refine_ls_R_factor_gt           0.0377

_refine_ls_wR_factor_ref         0.0776

_refine_ls_wR_factor_gt          0.0685

_refine_ls_goodness_of_fit_ref   1.042

_refine_ls_restrained_S_all      1.042

_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_symmetry_multiplicity

_atom_site_calc_flag

_atom_site_refinement_flags

_atom_site_disorder_assembly

_atom_site_disorder_group


























I1 I 0.38759(5) 1.16502(4) -0.16014(4) 0.05811(15) Uani 1 1 d . . .
I2 I 0.27619(6) 0.71652(5) -0.09441(5) 0.07413(18) Uani 1 1 d . . .
F1 F 0.0511(5) 0.6231(4) 0.1876(4) 0.0891(13) Uani 1 1 d . . .
F2 F -0.0504(5) 0.7958(5) 0.3712(4) 0.0929(12) Uani 1 1 d . . .
F3 F 0.0363(5) 1.1221(5) 0.3241(4) 0.0868(12) Uani 1 1 d . . .
F4 F 0.2198(5) 1.2788(4) 0.0920(4) 0.0783(11) Uani 1 1 d . . .
O2 O 0.4682(6) 0.6228(4) 0.6489(4) 0.0622(11) Uani 1 1 d . . .
O3 O 0.6493(5) 0.3270(4) 0.6018(4) 0.0646(11) Uani 1 1 d . . .
C1 C 0.7193(8) 0.4903(7) 0.5650(7) 0.0695(18) Uani 1 1 d . . .
H1A H 0.7033 0.5439 0.4784 0.083 Uiso 1 1 calc R . .
H1B H 0.8395 0.4885 0.5631 0.083 Uiso 1 1 calc R . .
C2 C 0.6340(9) 0.5834(7) 0.6613(7) 0.0709(19) Uani 1 1 d . . .
H2A H 0.6316 0.5173 0.7487 0.085 Uiso 1 1 calc R . .
H2B H 0.6990 0.6857 0.6502 0.085 Uiso 1 1 calc R . .
C3 C 0.4565(9) 0.7749(6) 0.5585(6) 0.075(2) Uani 1 1 d . . .
H3A H 0.5600 0.7977 0.4922 0.090 Uiso 1 1 calc R . .
H3B H 0.4426 0.8652 0.6034 0.090 Uiso 1 1 calc R . .
C4 C 0.3125(10) 0.7660(7) 0.4963(7) 0.081(2) Uani 1 1 d . . .
H4A H 0.2153 0.7142 0.5620 0.097 Uiso 1 1 calc R . .
H4B H 0.2838 0.8778 0.4573 0.097 Uiso 1 1 calc R . .
C5 C 0.2355(6) 1.0329(6) 0.0149(5) 0.0436(13) Uani 1 1 d . . .
C6 C 0.1910(7) 0.8627(6) 0.0394(6) 0.0491(14) Uani 1 1 d . . .
C7 C 0.0969(8) 0.7860(7) 0.1598(6) 0.0551(15) Uani 1 1 d . . .
C8 C 0.0435(7) 0.8724(8) 0.2543(6) 0.0585(16) Uani 1 1 d . . .
C9 C 0.0861(8) 1.0380(8) 0.2303(6) 0.0584(15) Uani 1 1 d . . .
C10 C 0.1806(7) 1.1145(7) 0.1113(6) 0.0522(14) 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 C5 2.092(5) . ?
I2 C6 2.089(6) . ?
F1 C7 1.347(6) . ?
F2 C8 1.346(6) . ?
F3 C9 1.343(7) . ?
F4 C10 1.355(6) . ?
O2 C2 1.404(7) . ?
O2 C3 1.418(6) . ?
O3 C1 1.405(6) . ?
O3 C4 1.423(7) 2_666 ?
C1 C2 1.481(9) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.471(9) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 O3 1.423(7) 2_666 ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C10 1.359(7) . ?
C5 C6 1.405(7) . ?
C6 C7 1.373(8) . ?
C7 C8 1.366(9) . ?
C8 C9 1.366(8) . ?
C9 C10 1.363(8) . ?



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 O2 C3 114.0(5) . . ?
C1 O3 C4 115.1(5) . 2_666 ?
O3 C1 C2 108.4(5) . . ?
O3 C1 H1A 110.0 . . ?
C2 C1 H1A 110.0 . . ?
O3 C1 H1B 110.0 . . ?
C2 C1 H1B 110.0 . . ?
H1A C1 H1B 108.4 . . ?
O2 C2 C1 112.9(5) . . ?
O2 C2 H2A 109.0 . . ?
C1 C2 H2A 109.0 . . ?
O2 C2 H2B 109.0 . . ?
C1 C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?
O2 C3 C4 110.5(5) . . ?
O2 C3 H3A 109.6 . . ?
C4 C3 H3A 109.6 . . ?
O2 C3 H3B 109.6 . . ?
C4 C3 H3B 109.6 . . ?
H3A C3 H3B 108.1 . . ?
O3 C4 C3 111.2(6) 2_666 . ?
O3 C4 H4A 109.4 2_666 . ?
C3 C4 H4A 109.4 . . ?
O3 C4 H4B 109.4 2_666 . ?
C3 C4 H4B 109.4 . . ?
H4A C4 H4B 108.0 . . ?
C10 C5 C6 118.1(5) . . ?
C10 C5 I1 118.4(4) . . ?
C6 C5 I1 123.4(4) . . ?
C7 C6 C5 118.8(5) . . ?
C7 C6 I2 118.2(4) . . ?
C5 C6 I2 122.9(4) . . ?
F1 C7 C8 117.8(6) . . ?
F1 C7 C6 120.8(6) . . ?
C8 C7 C6 121.4(5) . . ?
F2 C8 C7 120.7(6) . . ?
F2 C8 C9 119.4(6) . . ?
C7 C8 C9 119.9(6) . . ?
F3 C9 C10 121.2(6) . . ?
F3 C9 C8 119.8(6) . . ?
C10 C9 C8 118.9(6) . . ?
F4 C10 C5 120.3(5) . . ?
F4 C10 C9 116.9(5) . . ?
C5 C10 C9 122.8(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





























C4 O3 C1 C2 165.4(6) 2_666 . . . ?
C3 O2 C2 C1 -87.6(6) . . . . ?
O3 C1 C2 O2 -72.9(7) . . . . ?
C2 O2 C3 C4 148.5(6) . . . . ?
O2 C3 C4 O3 -77.2(7) . . . 2_666 ?
C10 C5 C6 C7 -1.0(8) . . . . ?
I1 C5 C6 C7 177.1(4) . . . . ?
C10 C5 C6 I2 -176.5(4) . . . . ?
I1 C5 C6 I2 1.6(6) . . . . ?
C5 C6 C7 F1 179.9(5) . . . . ?
I2 C6 C7 F1 -4.4(7) . . . . ?
C5 C6 C7 C8 1.3(9) . . . . ?
I2 C6 C7 C8 177.0(4) . . . . ?
F1 C7 C8 F2 0.5(9) . . . . ?
C6 C7 C8 F2 179.2(5) . . . . ?
F1 C7 C8 C9 -179.7(5) . . . . ?
C6 C7 C8 C9 -1.0(9) . . . . ?
F2 C8 C9 F3 1.0(9) . . . . ?
C7 C8 C9 F3 -178.8(6) . . . . ?
F2 C8 C9 C10 -179.7(5) . . . . ?
C7 C8 C9 C10 0.5(9) . . . . ?
C6 C5 C10 F4 -179.8(5) . . . . ?
I1 C5 C10 F4 2.0(7) . . . . ?
C6 C5 C10 C9 0.6(9) . . . . ?
I1 C5 C10 C9 -177.6(5) . . . . ?
F3 C9 C10 F4 -0.7(9) . . . . ?
C8 C9 C10 F4 -180.0(5) . . . . ?
F3 C9 C10 C5 179.0(5) . . . . ?
C8 C9 C10 C5 -0.3(9) . . . . ?



_diffrn_measured_fraction_theta_max 0.998

_diffrn_reflns_theta_full        25.49

_diffrn_measured_fraction_theta_full 0.998

_refine_diff_density_max         0.806

_refine_diff_density_min         -0.774

_refine_diff_density_rms         0.108

####################################################################### 
# 
# 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_C5-I12
_database_code_depnum_ccdc_archive 'CCDC 2281931'
loop_
_audit_author_name
_audit_author_address
'Weizhou Wang'
;Luoyang Normal University
China
;
_audit_update_record             
;
2023-07-17 deposited with the CCDC.	2024-09-11 downloaded from the CCDC.
;



_audit_creation_method           SHELXL-97

_chemical_name_systematic        
;

 ?

;

_chemical_name_common            ?

_chemical_melting_point          ?

_chemical_formula_moiety         ?

_chemical_formula_sum            'C16 H20 F4 I2 O5'

_chemical_formula_weight         622.12



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'



_symmetry_cell_setting           Monoclinic

_symmetry_space_group_name_H-M   P2(1)/c



loop_

_symmetry_equiv_pos_as_xyz




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



_cell_length_a                   12.3775(18)

_cell_length_b                   7.6176(10)

_cell_length_c                   22.623(3)

_cell_angle_alpha                90.00

_cell_angle_beta                 100.287(13)

_cell_angle_gamma                90.00

_cell_volume                     2098.8(5)

_cell_formula_units_Z            4

_cell_measurement_temperature    295(2)

_cell_measurement_reflns_used    2860

_cell_measurement_theta_min      3.4690

_cell_measurement_theta_max      28.8060



_exptl_crystal_description       block

_exptl_crystal_colour            colourless

_exptl_crystal_size_max          0.40

_exptl_crystal_size_mid          0.30

_exptl_crystal_size_min          0.10

_exptl_crystal_density_meas      ?

_exptl_crystal_density_diffrn    1.969

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             1192

_exptl_absorpt_coefficient_mu    3.054

_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.3746

_exptl_absorpt_correction_T_max  0.7499

_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;



_exptl_special_details           
;

 ?

;



_diffrn_ambient_temperature      295(2)

_diffrn_radiation_wavelength     0.71073

_diffrn_radiation_type           MoK\a

_diffrn_radiation_source         'Enhance (Mo) X-ray Source'

_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'

_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 16.2542

_diffrn_standards_number         0

_diffrn_standards_interval_count ?

_diffrn_standards_interval_time  ?

_diffrn_standards_decay_%        ?

_diffrn_reflns_number            8868

_diffrn_reflns_av_R_equivalents  0.1102

_diffrn_reflns_av_sigmaI/netI    0.1031

_diffrn_reflns_limit_h_min       -14

_diffrn_reflns_limit_h_max       9

_diffrn_reflns_limit_k_min       -8

_diffrn_reflns_limit_k_max       9

_diffrn_reflns_limit_l_min       -27

_diffrn_reflns_limit_l_max       27

_diffrn_reflns_theta_min         3.15

_diffrn_reflns_theta_max         25.50

_reflns_number_total             3884

_reflns_number_gt                2728

_reflns_threshold_expression     >2sigma(I)



_computing_data_collection       'Bruker FRAMBO'

_computing_cell_refinement       'Bruker FRAMBO'

_computing_data_reduction        'Bruker SAINT'

_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

_computing_molecular_graphics    'Bruker SHELXTL'

_computing_publication_material  'Bruker SHELXTL'



_refine_special_details          
;

 Refinement of F² against ALL reflections.  The weighted R-factor wR and

 goodness of fit S are based on F², conventional R-factors R are based

 on F, with F set to zero for negative F². The threshold expression of

 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is

 not relevant to the choice of reflections for refinement.  R-factors based

 on F² are statistically about twice as large as those based on F, and R-

 factors based on ALL data will be even larger.

;



_refine_ls_structure_factor_coef Fsqd

_refine_ls_matrix_type           full

_refine_ls_weighting_scheme      calc

_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.2000P)²+6.3105P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_primary     direct

_atom_sites_solution_secondary   difmap

_atom_sites_solution_hydrogens   geom

_refine_ls_hydrogen_treatment    constr

_refine_ls_extinction_method     SHELXL

_refine_ls_extinction_coef       0.0061(10)

_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^

_refine_ls_number_reflns         3884

_refine_ls_number_parameters     238

_refine_ls_number_restraints     37

_refine_ls_R_factor_all          0.1262

_refine_ls_R_factor_gt           0.0878

_refine_ls_wR_factor_ref         0.3317

_refine_ls_wR_factor_gt          0.2460

_refine_ls_goodness_of_fit_ref   1.128

_refine_ls_restrained_S_all      1.124

_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_symmetry_multiplicity

_atom_site_calc_flag

_atom_site_refinement_flags

_atom_site_disorder_assembly

_atom_site_disorder_group




























































C13 C 0.6913(11) 0.3365(18) 0.6561(7) 0.106(5) Uani 0.648(14) 1 d PGU A 1
H13A H 0.6629 0.3116 0.6925 0.127 Uiso 0.648(14) 1 calc PR A 1
H13B H 0.6845 0.2329 0.6308 0.127 Uiso 0.648(14) 1 calc PR A 1
C14 C 0.6357(8) 0.4961(14) 0.6229(6) 0.098(5) Uani 0.648(14) 1 d PGU A 1
H14A H 0.6581 0.6023 0.6455 0.118 Uiso 0.648(14) 1 calc PR A 1
H14B H 0.6567 0.5065 0.5838 0.118 Uiso 0.648(14) 1 calc PR A 1
C15 C 0.4662(10) 0.5847(17) 0.5692(6) 0.114(5) Uani 0.648(14) 1 d PGU A 1
H15A H 0.3892 0.5533 0.5587 0.137 Uiso 0.648(14) 1 calc PR A 1
H15B H 0.4996 0.5707 0.5338 0.137 Uiso 0.648(14) 1 calc PR A 1
C16 C 0.4773(12) 0.773(2) 0.5906(7) 0.091(4) Uani 0.648(14) 1 d PGU A 1
H16A H 0.5526 0.7960 0.6097 0.109 Uiso 0.648(14) 1 calc PR A 1
H16B H 0.4590 0.8519 0.5566 0.109 Uiso 0.648(14) 1 calc PR A 1
O5 O 0.5200(8) 0.4733(15) 0.6164(5) 0.094(4) Uani 0.648(14) 1 d PGU A 1
C13' C 0.6914(11) 0.3341(18) 0.6571(7) 0.106(5) Uani 0.352(14) 1 d PG A 2
H13C H 0.6482 0.3998 0.6814 0.127 Uiso 0.352(14) 1 calc PR A 2
H13D H 0.6924 0.2126 0.6700 0.127 Uiso 0.352(14) 1 calc PR A 2
C14' C 0.6349(11) 0.3441(17) 0.5921(6) 0.098(5) Uani 0.352(14) 1 d PG A 2
H14C H 0.6858 0.3111 0.5660 0.118 Uiso 0.352(14) 1 calc PR A 2
H14D H 0.5732 0.2637 0.5850 0.118 Uiso 0.352(14) 1 calc PR A 2
C15' C 0.4872(9) 0.5692(16) 0.5838(6) 0.114(5) Uani 0.352(14) 1 d PG A 2
H15C H 0.4641 0.5061 0.6167 0.137 Uiso 0.352(14) 1 calc PR A 2
H15D H 0.4374 0.5395 0.5470 0.137 Uiso 0.352(14) 1 calc PR A 2
C16' C 0.4841(12) 0.7649(19) 0.5949(7) 0.091(4) Uani 0.352(14) 1 d PG A 2
H16C H 0.5563 0.8048 0.6142 0.109 Uiso 0.352(14) 1 calc PR A 2
H16D H 0.4647 0.8261 0.5569 0.109 Uiso 0.352(14) 1 calc PR A 2
O5' O 0.5972(9) 0.5203(15) 0.5791(6) 0.094(4) Uani 0.352(14) 1 d PG A 2
C1 C 0.8547(11) 0.7502(16) 0.4633(6) 0.056(3) Uani 1 1 d . . .
C2 C 0.7854(10) 0.7962(17) 0.5027(7) 0.064(3) Uani 1 1 d . . .
C3 C 0.8255(10) 0.8354(17) 0.5601(6) 0.060(3) Uani 1 1 d . . .
C4 C 0.9383(9) 0.8225(15) 0.5810(5) 0.048(3) Uani 1 1 d . . .
C5 C 1.0096(9) 0.7750(13) 0.5442(5) 0.046(3) Uani 1 1 d . . .
C6 C 0.9637(10) 0.7464(14) 0.4816(5) 0.053(3) Uani 1 1 d . . .
C7 C 0.4231(11) 0.970(2) 0.6610(7) 0.080(4) Uani 1 1 d . A .
H7A H 0.3522 1.0199 0.6641 0.096 Uiso 1 1 calc R . .
H7B H 0.4571 1.0477 0.6356 0.096 Uiso 1 1 calc R . .
C8 C 0.4917(10) 0.968(2) 0.7215(7) 0.076(4) Uani 1 1 d . . .
H8A H 0.4884 1.0811 0.7409 0.092 Uiso 1 1 calc R . .
H8B H 0.4659 0.8788 0.7461 0.092 Uiso 1 1 calc R . .
C9 C 0.6740(11) 0.9333(18) 0.7678(5) 0.065(3) Uani 1 1 d . . .
H9A H 0.6439 0.8658 0.7974 0.078 Uiso 1 1 calc R . .
H9B H 0.6837 1.0532 0.7822 0.078 Uiso 1 1 calc R . .
C10 C 0.7828(10) 0.859(2) 0.7616(6) 0.065(3) Uani 1 1 d . . .
H10A H 0.8094 0.9148 0.7283 0.078 Uiso 1 1 calc R . .
H10B H 0.8358 0.8796 0.7980 0.078 Uiso 1 1 calc R . .
C11 C 0.8640(12) 0.587(3) 0.7430(7) 0.086(5) Uani 1 1 d . . .
H11A H 0.9176 0.5940 0.7799 0.103 Uiso 1 1 calc R . .
H11B H 0.8948 0.6441 0.7116 0.103 Uiso 1 1 calc R . .
C12 C 0.8441(16) 0.406(2) 0.7276(7) 0.091(5) Uani 1 1 d . A .
H12A H 0.9127 0.3414 0.7344 0.109 Uiso 1 1 calc R . .
H12B H 0.7958 0.3549 0.7523 0.109 Uiso 1 1 calc R . .
F1 F 0.8090(7) 0.7279(12) 0.4049(4) 0.076(2) Uani 1 1 d . . .
F2 F 0.6764(6) 0.8161(13) 0.4809(4) 0.084(3) Uani 1 1 d . . .
F3 F 0.7595(7) 0.8834(12) 0.5980(4) 0.080(2) Uani 1 1 d . . .
F4 F 0.9745(7) 0.8498(13) 0.6393(3) 0.076(2) Uani 1 1 d . . .
I1 I 1.06335(7) 0.68355(11) 0.41904(4) 0.0569(3) Uani 1 1 d . . .
I2 I 1.17507(6) 0.76590(12) 0.57920(4) 0.0615(3) Uani 1 1 d . . .
O1 O 0.4058(8) 0.8048(14) 0.6323(5) 0.079(3) Uani 1 1 d . . .
O2 O 0.6011(7) 0.9313(15) 0.7143(4) 0.071(3) Uani 1 1 d . . .
O3 O 0.7685(9) 0.6747(13) 0.7508(5) 0.075(3) Uani 1 1 d . . .
O4 O 0.7964(10) 0.3968(19) 0.6683(5) 0.096(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





























































C13 O4 1.361(17) . ?
C13 C14 1.527(6) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 O5 1.424(6) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 O5 1.433(6) . ?
C15 C16 1.514(6) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 O1 1.423(18) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C13' O4 1.366(17) . ?
C13' C14' 1.515(6) . ?
C13' H13C 0.9700 . ?
C13' H13D 0.9700 . ?
C14' O5' 1.433(6) . ?
C14' H14C 0.9700 . ?
C14' H14D 0.9700 . ?
C15' O5' 1.435(6) . ?
C15' C16' 1.514(6) . ?
C15' H15C 0.9700 . ?
C15' H15D 0.9700 . ?
C16' O1 1.427(17) . ?
C16' H16C 0.9700 . ?
C16' H16D 0.9700 . ?
C1 C6 1.339(17) . ?
C1 F1 1.352(15) . ?
C1 C2 1.387(18) . ?
C2 C3 1.339(19) . ?
C2 F2 1.360(15) . ?
C3 F3 1.338(13) . ?
C3 C4 1.396(17) . ?
C4 F4 1.333(13) . ?
C4 C5 1.366(15) . ?
C5 C6 1.444(17) . ?
C5 I2 2.061(11) . ?
C6 I1 2.093(12) . ?
C7 O1 1.416(18) . ?
C7 C8 1.48(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 O2 1.420(14) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 O2 1.373(15) . ?
C9 C10 1.490(19) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 O3 1.433(18) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 O3 1.397(17) . ?
C11 C12 1.43(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 O4 1.367(19) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?



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
















































































































O4 C13 C14 99.3(10) . . ?
O4 C13 H13A 111.9 . . ?
C14 C13 H13A 111.9 . . ?
O4 C13 H13B 111.9 . . ?
C14 C13 H13B 111.9 . . ?
H13A C13 H13B 109.6 . . ?
O5 C14 C13 108.1 . . ?
O5 C14 H14A 110.1 . . ?
C13 C14 H14A 110.1 . . ?
O5 C14 H14B 110.1 . . ?
C13 C14 H14B 110.1 . . ?
H14A C14 H14B 108.4 . . ?
O5 C15 C16 108.6 . . ?
O5 C15 H15A 110.0 . . ?
C16 C15 H15A 110.0 . . ?
O5 C15 H15B 110.0 . . ?
C16 C15 H15B 110.0 . . ?
H15A C15 H15B 108.3 . . ?
O1 C16 C15 109.9(9) . . ?
O1 C16 H16A 109.7 . . ?
C15 C16 H16A 109.7 . . ?
O1 C16 H16B 109.7 . . ?
C15 C16 H16B 109.7 . . ?
H16A C16 H16B 108.2 . . ?
C14 O5 C15 109.2 . . ?
O4 C13' C14' 114.9(10) . . ?
O4 C13' H13C 108.5 . . ?
C14' C13' H13C 108.5 . . ?
O4 C13' H13D 108.5 . . ?
C14' C13' H13D 108.5 . . ?
H13C C13' H13D 107.5 . . ?
O5' C14' C13' 108.8 . . ?
O5' C14' H14C 109.9 . . ?
C13' C14' H14C 109.9 . . ?
O5' C14' H14D 109.9 . . ?
C13' C14' H14D 109.9 . . ?
H14C C14' H14D 108.3 . . ?
O5' C15' C16' 108.7 . . ?
O5' C15' H15C 110.0 . . ?
C16' C15' H15C 110.0 . . ?
O5' C15' H15D 110.0 . . ?
C16' C15' H15D 110.0 . . ?
H15C C15' H15D 108.3 . . ?
O1 C16' C15' 110.3(9) . . ?
O1 C16' H16C 109.6 . . ?
C15' C16' H16C 109.6 . . ?
O1 C16' H16D 109.6 . . ?
C15' C16' H16D 109.6 . . ?
H16C C16' H16D 108.1 . . ?
C14' O5' C15' 120.4 . . ?
C6 C1 F1 121.5(11) . . ?
C6 C1 C2 120.7(13) . . ?
F1 C1 C2 117.4(12) . . ?
C3 C2 F2 119.9(12) . . ?
C3 C2 C1 121.0(12) . . ?
F2 C2 C1 118.8(13) . . ?
C2 C3 F3 121.4(12) . . ?
C2 C3 C4 119.2(11) . . ?
F3 C3 C4 119.4(11) . . ?
F4 C4 C5 120.4(10) . . ?
F4 C4 C3 117.6(10) . . ?
C5 C4 C3 121.9(11) . . ?
C4 C5 C6 116.9(10) . . ?
C4 C5 I2 118.7(9) . . ?
C6 C5 I2 124.2(8) . . ?
C1 C6 C5 120.0(11) . . ?
C1 C6 I1 118.6(9) . . ?
C5 C6 I1 121.4(8) . . ?
O1 C7 C8 115.5(13) . . ?
O1 C7 H7A 108.4 . . ?
C8 C7 H7A 108.4 . . ?
O1 C7 H7B 108.4 . . ?
C8 C7 H7B 108.4 . . ?
H7A C7 H7B 107.5 . . ?
O2 C8 C7 107.4(11) . . ?
O2 C8 H8A 110.2 . . ?
C7 C8 H8A 110.2 . . ?
O2 C8 H8B 110.2 . . ?
C7 C8 H8B 110.2 . . ?
H8A C8 H8B 108.5 . . ?
O2 C9 C10 112.1(11) . . ?
O2 C9 H9A 109.2 . . ?
C10 C9 H9A 109.2 . . ?
O2 C9 H9B 109.2 . . ?
C10 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
O3 C10 C9 107.5(10) . . ?
O3 C10 H10A 110.2 . . ?
C9 C10 H10A 110.2 . . ?
O3 C10 H10B 110.2 . . ?
C9 C10 H10B 110.2 . . ?
H10A C10 H10B 108.5 . . ?
O3 C11 C12 112.3(15) . . ?
O3 C11 H11A 109.1 . . ?
C12 C11 H11A 109.1 . . ?
O3 C11 H11B 109.1 . . ?
C12 C11 H11B 109.1 . . ?
H11A C11 H11B 107.9 . . ?
O4 C12 C11 108.4(14) . . ?
O4 C12 H12A 110.0 . . ?
C11 C12 H12A 110.0 . . ?
O4 C12 H12B 110.0 . . ?
C11 C12 H12B 110.0 . . ?
H12A C12 H12B 108.4 . . ?
C7 O1 C16 113.2(12) . . ?
C7 O1 C16' 113.5(11) . . ?
C16 O1 C16' 5.37(7) . . ?
C9 O2 C8 112.8(10) . . ?
C11 O3 C10 114.2(12) . . ?
C13 O4 C13' 1.2 . . ?
C13 O4 C12 116.4(12) . . ?
C13' O4 C12 115.4(12) . . ?



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



















































O4 C13 C14 O5 -168.6(10) . . . . ?
O5 C15 C16 O1 -74.2(10) . . . . ?
C13 C14 O5 C15 -160.3 . . . . ?
C16 C15 O5 C14 -71.3 . . . . ?
O4 C13' C14' O5' -79.1(11) . . . . ?
O5' C15' C16' O1 -146.7(10) . . . . ?
C13' C14' O5' C15' -94.0 . . . . ?
C16' C15' O5' C14' 155.4 . . . . ?
C6 C1 C2 C3 -1.0(19) . . . . ?
F1 C1 C2 C3 -174.1(12) . . . . ?
C6 C1 C2 F2 173.3(11) . . . . ?
F1 C1 C2 F2 0.1(17) . . . . ?
F2 C2 C3 F3 4(2) . . . . ?
C1 C2 C3 F3 178.6(12) . . . . ?
F2 C2 C3 C4 -176.9(11) . . . . ?
C1 C2 C3 C4 -2.7(19) . . . . ?
C2 C3 C4 F4 -175.1(12) . . . . ?
F3 C3 C4 F4 3.6(17) . . . . ?
C2 C3 C4 C5 1.6(18) . . . . ?
F3 C3 C4 C5 -179.7(11) . . . . ?
F4 C4 C5 C6 179.5(10) . . . . ?
C3 C4 C5 C6 2.8(16) . . . . ?
F4 C4 C5 I2 -4.8(14) . . . . ?
C3 C4 C5 I2 178.5(9) . . . . ?
F1 C1 C6 C5 178.5(10) . . . . ?
C2 C1 C6 C5 5.6(17) . . . . ?
F1 C1 C6 I1 -5.2(15) . . . . ?
C2 C1 C6 I1 -178.1(9) . . . . ?
C4 C5 C6 C1 -6.4(15) . . . . ?
I2 C5 C6 C1 178.1(8) . . . . ?
C4 C5 C6 I1 177.4(7) . . . . ?
I2 C5 C6 I1 1.9(12) . . . . ?
O1 C7 C8 O2 70.4(16) . . . . ?
O2 C9 C10 O3 -69.1(15) . . . . ?
O3 C11 C12 O4 77.0(17) . . . . ?
C8 C7 O1 C16 -98.3(16) . . . . ?
C8 C7 O1 C16' -92.5(16) . . . . ?
C15 C16 O1 C7 171.3(9) . . . . ?
C15 C16 O1 C16' 77.0(3) . . . . ?
C15' C16' O1 C7 160.0(10) . . . . ?
C15' C16' O1 C16 -112.0(3) . . . . ?
C10 C9 O2 C8 168.3(12) . . . . ?
C7 C8 O2 C9 177.4(12) . . . . ?
C12 C11 O3 C10 -175.2(13) . . . . ?
C9 C10 O3 C11 179.0(11) . . . . ?
C14 C13 O4 C13' 151.0(4) . . . . ?
C14 C13 O4 C12 120.4(13) . . . . ?
C14' C13' O4 C13 23.5(7) . . . . ?
C14' C13' O4 C12 173.2(11) . . . . ?
C11 C12 O4 C13 -114.4(17) . . . . ?
C11 C12 O4 C13' -115.1(17) . . . . ?



_diffrn_measured_fraction_theta_max 0.996

_diffrn_reflns_theta_full        25.50

_diffrn_measured_fraction_theta_full 0.996

_refine_diff_density_max         1.965

_refine_diff_density_min         -1.801

_refine_diff_density_rms         0.381

# start Validation Reply Form
_vrf_PLAT431_C5-I12              
;
PROBLEM: Short Inter HL..A Contact I2 ..O1 . 2.91 Ang.
RESPONSE: The Checkcif software has a bug and cannot identify the halogen bond.
;
# end Validation Reply Form
####################################################################### 
# 
# 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_C6-I14
_database_code_depnum_ccdc_archive 'CCDC 2379639'
loop_
_audit_author_name
_audit_author_address
'Weizhou Wang'
;Luoyang Normal University
China
;
_audit_update_record             
;
2024-08-25 deposited with the CCDC.	2024-09-11 downloaded from the CCDC.
;
_audit_creation_date             2024-08-25
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H24 O6, C6 F4 I2'
_chemical_formula_sum            'C18 H24 F4 I2 O6'
_chemical_formula_weight         666.17
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   14.2455(5)
_cell_length_b                   10.6548(5)
_cell_length_c                   15.5033(5)
_cell_angle_alpha                90
_cell_angle_beta                 94.012(3)
_cell_angle_gamma                90
_cell_volume                     2347.37(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6798
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.8580
_cell_measurement_theta_min      3.7470
_shelx_estimated_absorpt_T_max   0.597
_shelx_estimated_absorpt_T_min   0.447
_exptl_absorpt_coefficient_mu    2.741
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65569
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.92a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.885
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1288
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.21
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.888
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12761
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.888
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.232
_diffrn_reflns_theta_min         3.482
_diffrn_ambient_temperature      296(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0584
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.888
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      0.00  84.00   1.00    4.89    --   16.93  57.00  60.00   84
  2  ω    -10.00  42.00   1.00    4.89    --   16.93  77.00 150.00   52
  3  ω    -10.00  42.00   1.00    4.89    --   16.93  77.00 -60.00   52
  4  ω     -2.00  86.00   1.00    4.89    --   16.93  38.00  90.00   88
  5  ω    -50.00  34.00   1.00    4.89    --   16.93 -57.00-180.00   84
  6  ω    -52.00  36.00   1.00    4.89    --   16.93 -38.00 -90.00   88
  7  ω    -85.00 -35.00   1.00    4.89    --  -15.84 -38.00 150.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0464908000
_diffrn_orient_matrix_UB_12      0.0060761000
_diffrn_orient_matrix_UB_13      0.0131889000
_diffrn_orient_matrix_UB_21      -0.0049222000
_diffrn_orient_matrix_UB_22      0.0577447000
_diffrn_orient_matrix_UB_23      -0.0226017000
_diffrn_orient_matrix_UB_31      -0.0175554000
_diffrn_orient_matrix_UB_32      -0.0324222000
_diffrn_orient_matrix_UB_33      -0.0376954000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2552
_reflns_number_total             2841
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.92a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.92a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.92a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.482
_refine_diff_density_min         -0.562
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       0.0109(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2841
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0317
_refine_ls_R_factor_gt           0.0268
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0190P)²+2.0558P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0524
_refine_ls_wR_factor_ref         0.0544
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C5(H5A,H5B), C6(H6A,H6B), C8(H8A,H8B), C7(H7A,H7B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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 0.68794(2) 0.45078(2) 0.37138(2) 0.04894(10) Uani 1 1 d . . . . .
F1 F 0.63747(11) 0.67397(15) 0.49622(11) 0.0649(5) Uani 1 1 d . . . . .
F2 F 0.49632(12) 0.71065(15) 0.59628(11) 0.0675(5) Uani 1 1 d . . . . .
C2 C 0.57032(17) 0.5860(2) 0.49794(15) 0.0379(5) Uani 1 1 d . . . . .
C3 C 0.49680(17) 0.6053(2) 0.54912(15) 0.0391(5) Uani 1 1 d . . . . .
C1 C 0.57581(16) 0.4804(2) 0.44726(14) 0.0342(5) Uani 1 1 d . . . . .
O1 O 0.87423(12) 0.39631(17) 0.29128(11) 0.0492(4) Uani 1 1 d . . . . .
O3 O 0.73035(13) 0.00058(18) 0.35357(13) 0.0572(5) Uani 1 1 d . . . . .
O2 O 0.92486(13) 0.09497(19) 0.38604(13) 0.0565(5) Uani 1 1 d . . . . .
C9 C 0.6578(2) -0.0652(3) 0.3061(2) 0.0558(7) Uani 1 1 d . . . . .
H9A H 0.629101 -0.125378 0.343160 0.067 Uiso 1 1 calc R U . . .
H9B H 0.683186 -0.110359 0.258671 0.067 Uiso 1 1 calc R U . . .
C5 C 0.92810(17) 0.2885(2) 0.31242(16) 0.0438(6) Uani 1 1 d . . . . .
H5A H 0.987652 0.312140 0.342165 0.053 Uiso 1 1 calc R U . . .
H5B H 0.940921 0.243209 0.260263 0.053 Uiso 1 1 calc R U . . .
C6 C 0.87321(18) 0.2075(2) 0.36964(17) 0.0466(6) Uani 1 1 d . . . . .
H6A H 0.864135 0.250601 0.423537 0.056 Uiso 1 1 calc R U . . .
H6B H 0.811901 0.188582 0.341456 0.056 Uiso 1 1 calc R U . . .
C4 C 0.9136(2) 0.4722(3) 0.22786(19) 0.0501(7) Uani 1 1 d . . . . .
C8 C 0.8083(2) -0.0733(3) 0.3819(2) 0.0641(8) Uani 1 1 d . . . . .
H8A H 0.837785 -0.107051 0.332399 0.077 Uiso 1 1 calc R U . . .
H8B H 0.787661 -0.143009 0.416078 0.077 Uiso 1 1 calc R U . . .
C7 C 0.8775(2) 0.0045(3) 0.4351(2) 0.0634(8) Uani 1 1 d . . . . .
H7A H 0.844889 0.047781 0.479257 0.076 Uiso 1 1 calc R U . . .
H7B H 0.923881 -0.050473 0.464129 0.076 Uiso 1 1 calc R U . . .
H4A H 0.9290(18) 0.419(2) 0.1770(17) 0.046(7) Uiso 1 1 d . . . . .
H4B H 0.970(2) 0.518(3) 0.2563(17) 0.056(8) Uiso 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 C1 2.073(2) . ?
F1 C2 1.341(3) . ?
F2 C3 1.340(3) . ?
C2 C3 1.373(3) . ?
C2 C1 1.378(3) . ?
C3 C1 1.384(3) 5_666 ?
O1 C5 1.407(3) . ?
O1 C4 1.419(3) . ?
O3 C9 1.412(3) . ?
O3 C8 1.405(3) . ?
O2 C6 1.420(3) . ?
O2 C7 1.426(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C4 1.490(4) 7_655 ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.497(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C4 H4A 1.01(3) . ?
C4 H4B 1.01(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C7 1.492(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?

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
F1 C2 C3 118.8(2) . . ?
F1 C2 C1 119.4(2) . . ?
C3 C2 C1 121.8(2) . . ?
F2 C3 C2 118.3(2) . . ?
F2 C3 C1 119.9(2) . 5_666 ?
C2 C3 C1 121.9(2) . 5_666 ?
C2 C1 I1 121.65(18) . . ?
C2 C1 C3 116.3(2) . 5_666 ?
C3 C1 I1 122.03(16) 5_666 . ?
C5 O1 C4 113.01(19) . . ?
C8 O3 C9 114.7(2) . . ?
C6 O2 C7 114.0(2) . . ?
O3 C9 H9A 110.1 . . ?
O3 C9 H9B 110.1 . . ?
O3 C9 C4 108.1(2) . 7_655 ?
H9A C9 H9B 108.4 . . ?
C4 C9 H9A 110.1 7_655 . ?
C4 C9 H9B 110.1 7_655 . ?
O1 C5 H5A 110.1 . . ?
O1 C5 H5B 110.1 . . ?
O1 C5 C6 108.04(19) . . ?
H5A C5 H5B 108.4 . . ?
C6 C5 H5A 110.1 . . ?
C6 C5 H5B 110.1 . . ?
O2 C6 C5 107.9(2) . . ?
O2 C6 H6A 110.1 . . ?
O2 C6 H6B 110.1 . . ?
C5 C6 H6A 110.1 . . ?
C5 C6 H6B 110.1 . . ?
H6A C6 H6B 108.4 . . ?
O1 C4 C9 109.3(2) . 7_655 ?
O1 C4 H4A 109.6(15) . . ?
O1 C4 H4B 108.1(16) . . ?
C9 C4 H4A 106.3(15) 7_655 . ?
C9 C4 H4B 109.5(16) 7_655 . ?
H4A C4 H4B 114(2) . . ?
O3 C8 H8A 109.7 . . ?
O3 C8 H8B 109.7 . . ?
O3 C8 C7 109.8(2) . . ?
H8A C8 H8B 108.2 . . ?
C7 C8 H8A 109.7 . . ?
C7 C8 H8B 109.7 . . ?
O2 C7 C8 113.5(2) . . ?
O2 C7 H7A 108.9 . . ?
O2 C7 H7B 108.9 . . ?
C8 C7 H7A 108.9 . . ?
C8 C7 H7B 108.9 . . ?
H7A C7 H7B 107.7 . . ?

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
F1 C2 C3 F2 -1.1(3) . . . . ?
F1 C2 C3 C1 178.8(2) . . . 5_666 ?
F1 C2 C1 I1 2.2(3) . . . . ?
F1 C2 C1 C3 -178.8(2) . . . 5_666 ?
C3 C2 C1 I1 -179.16(18) . . . . ?
C3 C2 C1 C3 -0.1(4) . . . 5_666 ?
C1 C2 C3 F2 -179.7(2) . . . . ?
C1 C2 C3 C1 0.1(4) . . . 5_666 ?
O1 C5 C6 O2 176.09(19) . . . . ?
O3 C8 C7 O2 -70.5(3) . . . . ?
C9 O3 C8 C7 -176.9(2) . . . . ?
C5 O1 C4 C9 166.2(2) . . . 7_655 ?
C6 O2 C7 C8 82.7(3) . . . . ?
C4 O1 C5 C6 -172.0(2) . . . . ?
C8 O3 C9 C4 -173.4(2) . . . 7_655 ?
C7 O2 C6 C5 -175.8(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.388
_oxdiff_exptl_absorpt_empirical_full_min 0.790
####################################################################### 
# 
# 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_C5-I14
_database_code_depnum_ccdc_archive 'CCDC 2281933'
loop_
_audit_author_name
_audit_author_address
'Weizhou Wang'
;Luoyang Normal University
China
;
_audit_update_record             
;
2023-07-17 deposited with the CCDC.	2024-09-11 downloaded from the CCDC.
;



_audit_creation_method           SHELXL-97

_chemical_name_systematic        
;

 ?

;

_chemical_name_common            ?

_chemical_melting_point          ?

_chemical_formula_moiety         ?

_chemical_formula_sum            'C32 H40 F8 I4 O10'

_chemical_formula_weight         1244.24



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'



_symmetry_cell_setting           Triclinic

_symmetry_space_group_name_H-M   P-1



loop_

_symmetry_equiv_pos_as_xyz


'x, y, z'
'-x, -y, -z'



_cell_length_a                   9.7355(6)

_cell_length_b                   12.4217(7)

_cell_length_c                   18.1787(11)

_cell_angle_alpha                88.582(5)

_cell_angle_beta                 80.631(5)

_cell_angle_gamma                78.136(5)

_cell_volume                     2122.6(2)

_cell_formula_units_Z            2

_cell_measurement_temperature    296(2)

_cell_measurement_reflns_used    4395

_cell_measurement_theta_min      3.4960

_cell_measurement_theta_max      26.1040



_exptl_crystal_description       block

_exptl_crystal_colour            colourless

_exptl_crystal_size_max          0.21

_exptl_crystal_size_mid          0.17

_exptl_crystal_size_min          0.12

_exptl_crystal_density_meas      ?

_exptl_crystal_density_diffrn    1.947

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             1192

_exptl_absorpt_coefficient_mu    3.020

_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.5696

_exptl_absorpt_correction_T_max  0.7133

_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;



_exptl_special_details           
;

 ?

;



_diffrn_ambient_temperature      296(2)

_diffrn_radiation_wavelength     0.71073

_diffrn_radiation_type           MoK\a

_diffrn_radiation_source         'Enhance (Mo) X-ray Source'

_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'

_diffrn_detector_area_resol_mean 16.2542

_diffrn_measurement_method       'phi and omega scans'

_diffrn_standards_number         ?

_diffrn_standards_interval_count ?

_diffrn_standards_interval_time  ?

_diffrn_standards_decay_%        ?

_diffrn_reflns_number            17211

_diffrn_reflns_av_R_equivalents  0.0383

_diffrn_reflns_av_sigmaI/netI    0.0569

_diffrn_reflns_limit_h_min       -11

_diffrn_reflns_limit_h_max       11

_diffrn_reflns_limit_k_min       -15

_diffrn_reflns_limit_k_max       11

_diffrn_reflns_limit_l_min       -22

_diffrn_reflns_limit_l_max       22

_diffrn_reflns_theta_min         3.33

_diffrn_reflns_theta_max         25.50

_reflns_number_total             7872

_reflns_number_gt                5271

_reflns_threshold_expression     >2sigma(I)



_computing_data_collection       'Bruker FRAMBO'

_computing_cell_refinement       'Bruker FRAMBO'

_computing_data_reduction        'Bruker SAINT'

_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

_computing_molecular_graphics    'Bruker SHELXTL'

_computing_publication_material  'Bruker SHELXTL'



_refine_special_details          
;

 Refinement of F² against ALL reflections.  The weighted R-factor wR and

 goodness of fit S are based on F², conventional R-factors R are based

 on F, with F set to zero for negative F². The threshold expression of

 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is

 not relevant to the choice of reflections for refinement.  R-factors based

 on F² are statistically about twice as large as those based on F, and R-

 factors based on ALL data will be even larger.

;



_refine_ls_structure_factor_coef Fsqd

_refine_ls_matrix_type           full

_refine_ls_weighting_scheme      calc

_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0828P)²+5.1419P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_primary     direct

_atom_sites_solution_secondary   difmap

_atom_sites_solution_hydrogens   geom

_refine_ls_hydrogen_treatment    constr

_refine_ls_extinction_method     SHELXL

_refine_ls_extinction_coef       0.0054(5)

_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^

_refine_ls_number_reflns         7872

_refine_ls_number_parameters     488

_refine_ls_number_restraints     0

_refine_ls_R_factor_all          0.0930

_refine_ls_R_factor_gt           0.0607

_refine_ls_wR_factor_ref         0.1778

_refine_ls_wR_factor_gt          0.1542

_refine_ls_goodness_of_fit_ref   1.033

_refine_ls_restrained_S_all      1.033

_refine_ls_shift/su_max          0.004

_refine_ls_shift/su_mean         0.001



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_symmetry_multiplicity

_atom_site_calc_flag

_atom_site_refinement_flags

_atom_site_disorder_assembly

_atom_site_disorder_group






























































































C1 C 0.8970(9) 0.4560(6) 0.1802(4) 0.0488(19) Uani 1 1 d . . .
C2 C 0.9991(10) 0.4579(7) 0.1199(5) 0.058(2) Uani 1 1 d . . .
C3 C 1.0515(10) 0.5499(8) 0.1002(5) 0.066(3) Uani 1 1 d . . .
C4 C 1.0054(10) 0.6455(7) 0.1396(5) 0.062(2) Uani 1 1 d . . .
C5 C 0.9011(10) 0.6433(7) 0.2015(5) 0.059(2) Uani 1 1 d . . .
C6 C 0.8496(9) 0.5511(7) 0.2209(5) 0.058(2) Uani 1 1 d . . .
C7 C 0.2104(8) 0.4890(7) 0.2902(4) 0.0481(19) Uani 1 1 d . . .
C8 C 0.2040(10) 0.3787(7) 0.2881(4) 0.056(2) Uani 1 1 d . . .
C9 C 0.1040(10) 0.3369(7) 0.3352(4) 0.055(2) Uani 1 1 d . . .
C10 C 0.0022(10) 0.4019(9) 0.3848(5) 0.064(2) Uani 1 1 d . . .
C11 C 0.0108(9) 0.5098(9) 0.3868(5) 0.064(3) Uani 1 1 d . . .
C12 C 0.1089(9) 0.5531(7) 0.3409(5) 0.055(2) Uani 1 1 d . . .
C13 C 0.5562(13) 0.7875(9) 0.1585(8) 0.098(4) Uani 1 1 d . . .
H13A H 0.5971 0.7862 0.2039 0.118 Uiso 1 1 calc R . .
H13B H 0.6150 0.8210 0.1202 0.118 Uiso 1 1 calc R . .
C14 C 0.4209(12) 0.8545(9) 0.1711(8) 0.092(4) Uani 1 1 d . . .
H14A H 0.3566 0.8169 0.2033 0.110 Uiso 1 1 calc R . .
H14B H 0.3858 0.8685 0.1240 0.110 Uiso 1 1 calc R . .
C15 C 0.2877(13) 1.0192(10) 0.2263(6) 0.090(4) Uani 1 1 d . . .
H15A H 0.2938 1.0696 0.2651 0.107 Uiso 1 1 calc R . .
H15B H 0.2257 0.9712 0.2485 0.107 Uiso 1 1 calc R . .
C16 C 0.2199(13) 1.0839(9) 0.1685(6) 0.086(3) Uani 1 1 d . . .
H16A H 0.1505 1.1463 0.1915 0.103 Uiso 1 1 calc R . .
H16B H 0.2912 1.1120 0.1341 0.103 Uiso 1 1 calc R . .
C17 C 0.1118(14) 1.0717(8) 0.0641(6) 0.084(3) Uani 1 1 d . . .
H17A H 0.0878 1.1509 0.0713 0.101 Uiso 1 1 calc R . .
H17B H 0.0276 1.0478 0.0545 0.101 Uiso 1 1 calc R . .
C18 C 0.2267(13) 1.0437(9) -0.0016(6) 0.084(3) Uani 1 1 d . . .
H18A H 0.1958 1.0804 -0.0455 0.101 Uiso 1 1 calc R . .
H18B H 0.3110 1.0684 0.0072 0.101 Uiso 1 1 calc R . .
C19 C 0.3627(13) 0.8926(11) -0.0747(6) 0.099(4) Uani 1 1 d . . .
H19A H 0.4378 0.9340 -0.0780 0.119 Uiso 1 1 calc R . .
H19B H 0.3210 0.9049 -0.1200 0.119 Uiso 1 1 calc R . .
C20 C 0.4229(13) 0.7742(10) -0.0678(5) 0.087(4) Uani 1 1 d . . .
H20A H 0.3469 0.7340 -0.0547 0.105 Uiso 1 1 calc R . .
H20B H 0.4789 0.7453 -0.1149 0.105 Uiso 1 1 calc R . .
C21 C 0.5489(13) 0.6519(9) 0.0075(6) 0.084(3) Uani 1 1 d . . .
H21A H 0.6016 0.6094 -0.0359 0.101 Uiso 1 1 calc R . .
H21B H 0.4648 0.6222 0.0249 0.101 Uiso 1 1 calc R . .
C22 C 0.6386(11) 0.6411(9) 0.0670(5) 0.079(3) Uani 1 1 d . . .
H22A H 0.6834 0.5643 0.0708 0.094 Uiso 1 1 calc R . .
H22B H 0.7135 0.6820 0.0526 0.094 Uiso 1 1 calc R . .
O6 O 0.7114(7) 0.1222(5) 0.2705(4) 0.0746(19) Uani 1 1 d . . .
O10 O 0.4190(8) 0.2574(8) 0.4019(5) 0.106(3) Uani 1 1 d . . .
O9 O 0.5667(10) 0.2879(9) 0.5318(4) 0.110(3) Uani 1 1 d . . .
O7 O 0.7809(12) -0.0326(8) 0.3897(6) 0.117(3) Uani 1 1 d . . .
C23 C 0.7867(13) 0.0123(9) 0.2641(7) 0.088(3) Uani 1 1 d . . .
H23A H 0.8503 0.0025 0.2167 0.106 Uiso 1 1 calc R . .
H23B H 0.7196 -0.0357 0.2640 0.106 Uiso 1 1 calc R . .
O8 O 0.7301(16) 0.0767(12) 0.5329(7) 0.143(4) Uani 1 1 d . . .
C32 C 0.5735(12) 0.1399(10) 0.3133(6) 0.084(3) Uani 1 1 d . . .
H32A H 0.5577 0.0719 0.3373 0.101 Uiso 1 1 calc R . .
H32B H 0.5032 0.1618 0.2807 0.101 Uiso 1 1 calc R . .
C24 C 0.8699(15) -0.0209(11) 0.3243(8) 0.106(4) Uani 1 1 d . . .
H24A H 0.9359 -0.0901 0.3112 0.128 Uiso 1 1 calc R . .
H24B H 0.9246 0.0342 0.3310 0.128 Uiso 1 1 calc R . .
C31 C 0.5566(14) 0.2230(12) 0.3685(7) 0.108(4) Uani 1 1 d . . .
H31A H 0.6142 0.1949 0.4062 0.130 Uiso 1 1 calc R . .
H31B H 0.5914 0.2856 0.3455 0.130 Uiso 1 1 calc R . .
C29 C 0.4203(15) 0.3173(15) 0.5271(7) 0.125(5) Uani 1 1 d . . .
H29A H 0.3760 0.3786 0.5607 0.150 Uiso 1 1 calc R . .
H29B H 0.3756 0.2557 0.5429 0.150 Uiso 1 1 calc R . .
C30 C 0.3964(14) 0.3483(13) 0.4503(7) 0.115(5) Uani 1 1 d . . .
H30A H 0.2996 0.3891 0.4521 0.138 Uiso 1 1 calc R . .
H30B H 0.4598 0.3966 0.4303 0.138 Uiso 1 1 calc R . .
C28 C 0.597(2) 0.228(2) 0.5948(9) 0.159(8) Uani 1 1 d . . .
H28A H 0.6827 0.2459 0.6081 0.190 Uiso 1 1 calc R . .
H28B H 0.5203 0.2532 0.6355 0.190 Uiso 1 1 calc R . .
C27 C 0.617(3) 0.117(2) 0.5894(11) 0.165(9) Uani 1 1 d . . .
H27A H 0.5308 0.0977 0.5787 0.198 Uiso 1 1 calc R . .
H27B H 0.6365 0.0846 0.6366 0.198 Uiso 1 1 calc R . .
C25 C 0.850(3) -0.0674(16) 0.4524(13) 0.171(9) Uani 1 1 d . . .
H25A H 0.8815 -0.1468 0.4505 0.206 Uiso 1 1 calc R . .
H25B H 0.9328 -0.0349 0.4500 0.206 Uiso 1 1 calc R . .
C26 C 0.757(3) -0.036(2) 0.5206(11) 0.170(9) Uani 1 1 d . . .
H26A H 0.6679 -0.0593 0.5196 0.204 Uiso 1 1 calc R . .
H26B H 0.7994 -0.0739 0.5614 0.204 Uiso 1 1 calc R . .
F1 F 1.0505(7) 0.3661(4) 0.0780(3) 0.094(2) Uani 1 1 d . . .
F2 F 1.1500(7) 0.5458(5) 0.0393(4) 0.100(2) Uani 1 1 d . . .
F3 F 0.8527(7) 0.7335(4) 0.2449(4) 0.094(2) Uani 1 1 d . . .
F4 F 0.7490(6) 0.5546(5) 0.2820(3) 0.0831(17) Uani 1 1 d . . .
F5 F 0.2975(6) 0.3120(4) 0.2384(3) 0.0794(17) Uani 1 1 d . . .
F6 F 0.1036(7) 0.2294(4) 0.3309(3) 0.0842(17) Uani 1 1 d . . .
F7 F -0.0881(6) 0.5814(6) 0.4340(3) 0.095(2) Uani 1 1 d . . .
F8 F 0.1089(6) 0.6617(4) 0.3450(3) 0.0826(17) Uani 1 1 d . . .
I1 I 0.81929(7) 0.31518(5) 0.21214(4) 0.0655(2) Uani 1 1 d . . .
I2 I 1.08623(9) 0.78401(6) 0.11078(6) 0.1089(4) Uani 1 1 d . . .
I3 I 0.36588(7) 0.55333(5) 0.22323(3) 0.0645(2) Uani 1 1 d . . .
I4 I -0.15774(9) 0.34216(8) 0.45107(4) 0.0995(3) Uani 1 1 d . . .
O1 O 0.5638(7) 0.6787(5) 0.1369(3) 0.0713(18) Uani 1 1 d . . .
O2 O 0.4226(7) 0.9550(5) 0.2043(4) 0.080(2) Uani 1 1 d . . .
O3 O 0.1534(8) 1.0215(5) 0.1295(4) 0.081(2) Uani 1 1 d . . .
O4 O 0.2581(7) 0.9297(6) -0.0128(4) 0.0724(18) Uani 1 1 d . . .
O5 O 0.5080(8) 0.7618(6) -0.0127(4) 0.079(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






























































































C1 C2 1.357(11) . ?
C1 C6 1.365(11) . ?
C1 I1 2.079(8) . ?
C2 F1 1.347(9) . ?
C2 C3 1.363(13) . ?
C3 F2 1.335(10) . ?
C3 C4 1.358(13) . ?
C4 C5 1.392(13) . ?
C4 I2 2.057(9) . ?
C5 F3 1.344(9) . ?
C5 C6 1.359(13) . ?
C6 F4 1.351(10) . ?
C7 C12 1.370(10) . ?
C7 C8 1.387(12) . ?
C7 I3 2.064(8) . ?
C8 F5 1.337(9) . ?
C8 C9 1.365(12) . ?
C9 F6 1.340(10) . ?
C9 C10 1.366(12) . ?
C10 C11 1.362(14) . ?
C10 I4 2.061(9) . ?
C11 C12 1.351(13) . ?
C11 F7 1.368(10) . ?
C12 F8 1.352(10) . ?
C13 C14 1.393(15) . ?
C13 O1 1.400(13) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 O2 1.405(13) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 O2 1.391(12) . ?
C15 C16 1.468(15) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 O3 1.380(12) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 O3 1.408(12) . ?
C17 C18 1.490(16) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 O4 1.399(12) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 O4 1.406(12) . ?
C19 C20 1.478(16) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 O5 1.387(13) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 O5 1.399(12) . ?
C21 C22 1.484(15) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 O1 1.398(10) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
O6 C23 1.408(11) . ?
O6 C32 1.415(12) . ?
O10 C31 1.364(13) . ?
O10 C30 1.408(15) . ?
O9 C28 1.388(19) . ?
O9 C29 1.413(15) . ?
O7 C24 1.376(16) . ?
O7 C25 1.427(19) . ?
C23 C24 1.468(16) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
O8 C26 1.39(2) . ?
O8 C27 1.40(2) . ?
C32 C31 1.424(16) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C29 C30 1.482(18) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C28 C27 1.35(3) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C25 C26 1.42(3) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?



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 116.7(8) . . ?
C2 C1 I1 122.4(6) . . ?
C6 C1 I1 120.8(6) . . ?
F1 C2 C1 119.2(8) . . ?
F1 C2 C3 118.7(8) . . ?
C1 C2 C3 122.1(8) . . ?
F2 C3 C4 119.2(9) . . ?
F2 C3 C2 118.6(8) . . ?
C4 C3 C2 122.2(8) . . ?
C3 C4 C5 115.6(8) . . ?
C3 C4 I2 122.4(7) . . ?
C5 C4 I2 122.1(7) . . ?
F3 C5 C6 118.7(9) . . ?
F3 C5 C4 119.4(9) . . ?
C6 C5 C4 121.8(8) . . ?
F4 C6 C5 118.7(7) . . ?
F4 C6 C1 119.8(8) . . ?
C5 C6 C1 121.6(8) . . ?
C12 C7 C8 116.0(8) . . ?
C12 C7 I3 121.5(6) . . ?
C8 C7 I3 122.5(6) . . ?
F5 C8 C9 119.4(8) . . ?
F5 C8 C7 119.1(8) . . ?
C9 C8 C7 121.5(7) . . ?
F6 C9 C8 118.8(7) . . ?
F6 C9 C10 119.2(8) . . ?
C8 C9 C10 122.0(8) . . ?
C11 C10 C9 115.8(8) . . ?
C11 C10 I4 121.8(7) . . ?
C9 C10 I4 122.4(8) . . ?
C12 C11 C10 123.3(8) . . ?
C12 C11 F7 116.8(9) . . ?
C10 C11 F7 119.8(9) . . ?
C11 C12 F8 120.0(7) . . ?
C11 C12 C7 121.4(8) . . ?
F8 C12 C7 118.7(8) . . ?
C14 C13 O1 116.2(11) . . ?
C14 C13 H13A 108.2 . . ?
O1 C13 H13A 108.2 . . ?
C14 C13 H13B 108.2 . . ?
O1 C13 H13B 108.2 . . ?
H13A C13 H13B 107.4 . . ?
C13 C14 O2 111.3(11) . . ?
C13 C14 H14A 109.4 . . ?
O2 C14 H14A 109.4 . . ?
C13 C14 H14B 109.4 . . ?
O2 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
O2 C15 C16 117.1(10) . . ?
O2 C15 H15A 108.0 . . ?
C16 C15 H15A 108.0 . . ?
O2 C15 H15B 108.0 . . ?
C16 C15 H15B 108.0 . . ?
H15A C15 H15B 107.3 . . ?
O3 C16 C15 111.4(10) . . ?
O3 C16 H16A 109.3 . . ?
C15 C16 H16A 109.3 . . ?
O3 C16 H16B 109.3 . . ?
C15 C16 H16B 109.3 . . ?
H16A C16 H16B 108.0 . . ?
O3 C17 C18 111.7(9) . . ?
O3 C17 H17A 109.3 . . ?
C18 C17 H17A 109.3 . . ?
O3 C17 H17B 109.3 . . ?
C18 C17 H17B 109.3 . . ?
H17A C17 H17B 107.9 . . ?
O4 C18 C17 109.0(9) . . ?
O4 C18 H18A 109.9 . . ?
C17 C18 H18A 109.9 . . ?
O4 C18 H18B 109.9 . . ?
C17 C18 H18B 109.9 . . ?
H18A C18 H18B 108.3 . . ?
O4 C19 C20 110.4(9) . . ?
O4 C19 H19A 109.6 . . ?
C20 C19 H19A 109.6 . . ?
O4 C19 H19B 109.6 . . ?
C20 C19 H19B 109.6 . . ?
H19A C19 H19B 108.1 . . ?
O5 C20 C19 108.3(10) . . ?
O5 C20 H20A 110.0 . . ?
C19 C20 H20A 110.0 . . ?
O5 C20 H20B 110.0 . . ?
C19 C20 H20B 110.0 . . ?
H20A C20 H20B 108.4 . . ?
O5 C21 C22 111.4(9) . . ?
O5 C21 H21A 109.4 . . ?
C22 C21 H21A 109.4 . . ?
O5 C21 H21B 109.4 . . ?
C22 C21 H21B 109.4 . . ?
H21A C21 H21B 108.0 . . ?
O1 C22 C21 113.9(8) . . ?
O1 C22 H22A 108.8 . . ?
C21 C22 H22A 108.8 . . ?
O1 C22 H22B 108.8 . . ?
C21 C22 H22B 108.8 . . ?
H22A C22 H22B 107.7 . . ?
C23 O6 C32 116.0(9) . . ?
C31 O10 C30 114.4(10) . . ?
C28 O9 C29 114.4(12) . . ?
C24 O7 C25 115.5(15) . . ?
O6 C23 C24 113.3(9) . . ?
O6 C23 H23A 108.9 . . ?
C24 C23 H23A 108.9 . . ?
O6 C23 H23B 108.9 . . ?
C24 C23 H23B 108.9 . . ?
H23A C23 H23B 107.7 . . ?
C26 O8 C27 115.6(18) . . ?
O6 C32 C31 111.0(10) . . ?
O6 C32 H32A 109.4 . . ?
C31 C32 H32A 109.4 . . ?
O6 C32 H32B 109.4 . . ?
C31 C32 H32B 109.4 . . ?
H32A C32 H32B 108.0 . . ?
O7 C24 C23 110.1(12) . . ?
O7 C24 H24A 109.6 . . ?
C23 C24 H24A 109.6 . . ?
O7 C24 H24B 109.6 . . ?
C23 C24 H24B 109.6 . . ?
H24A C24 H24B 108.1 . . ?
O10 C31 C32 113.1(11) . . ?
O10 C31 H31A 108.9 . . ?
C32 C31 H31A 108.9 . . ?
O10 C31 H31B 108.9 . . ?
C32 C31 H31B 108.9 . . ?
H31A C31 H31B 107.8 . . ?
O9 C29 C30 111.7(10) . . ?
O9 C29 H29A 109.3 . . ?
C30 C29 H29A 109.3 . . ?
O9 C29 H29B 109.3 . . ?
C30 C29 H29B 109.3 . . ?
H29A C29 H29B 107.9 . . ?
O10 C30 C29 113.4(13) . . ?
O10 C30 H30A 108.9 . . ?
C29 C30 H30A 108.9 . . ?
O10 C30 H30B 108.9 . . ?
C29 C30 H30B 108.9 . . ?
H30A C30 H30B 107.7 . . ?
C27 C28 O9 116.8(17) . . ?
C27 C28 H28A 108.1 . . ?
O9 C28 H28A 108.1 . . ?
C27 C28 H28B 108.1 . . ?
O9 C28 H28B 108.1 . . ?
H28A C28 H28B 107.3 . . ?
C28 C27 O8 110(2) . . ?
C28 C27 H27A 109.6 . . ?
O8 C27 H27A 109.6 . . ?
C28 C27 H27B 109.6 . . ?
O8 C27 H27B 109.6 . . ?
H27A C27 H27B 108.1 . . ?
C26 C25 O7 111.4(17) . . ?
C26 C25 H25A 109.3 . . ?
O7 C25 H25A 109.3 . . ?
C26 C25 H25B 109.3 . . ?
O7 C25 H25B 109.3 . . ?
H25A C25 H25B 108.0 . . ?
O8 C26 C25 112(2) . . ?
O8 C26 H26A 109.2 . . ?
C25 C26 H26A 109.2 . . ?
O8 C26 H26B 109.2 . . ?
C25 C26 H26B 109.2 . . ?
H26A C26 H26B 107.9 . . ?
C22 O1 C13 119.4(9) . . ?
C15 O2 C14 113.4(9) . . ?
C16 O3 C17 113.9(9) . . ?
C18 O4 C19 114.6(9) . . ?
C20 O5 C21 112.5(9) . . ?



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 F1 179.6(8) . . . . ?
I1 C1 C2 F1 1.4(12) . . . . ?
C6 C1 C2 C3 -0.5(14) . . . . ?
I1 C1 C2 C3 -178.7(8) . . . . ?
F1 C2 C3 F2 1.1(15) . . . . ?
C1 C2 C3 F2 -178.8(9) . . . . ?
F1 C2 C3 C4 -179.9(9) . . . . ?
C1 C2 C3 C4 0.2(16) . . . . ?
F2 C3 C4 C5 179.0(9) . . . . ?
C2 C3 C4 C5 0.0(15) . . . . ?
F2 C3 C4 I2 -1.9(13) . . . . ?
C2 C3 C4 I2 179.1(8) . . . . ?
C3 C4 C5 F3 178.0(8) . . . . ?
I2 C4 C5 F3 -1.1(12) . . . . ?
C3 C4 C5 C6 0.1(14) . . . . ?
I2 C4 C5 C6 -179.0(7) . . . . ?
F3 C5 C6 F4 1.6(13) . . . . ?
C4 C5 C6 F4 179.6(8) . . . . ?
F3 C5 C6 C1 -178.3(8) . . . . ?
C4 C5 C6 C1 -0.4(14) . . . . ?
C2 C1 C6 F4 -179.3(8) . . . . ?
I1 C1 C6 F4 -1.1(12) . . . . ?
C2 C1 C6 C5 0.6(13) . . . . ?
I1 C1 C6 C5 178.8(7) . . . . ?
C12 C7 C8 F5 178.2(8) . . . . ?
I3 C7 C8 F5 -3.2(11) . . . . ?
C12 C7 C8 C9 -1.5(13) . . . . ?
I3 C7 C8 C9 177.1(7) . . . . ?
F5 C8 C9 F6 0.8(13) . . . . ?
C7 C8 C9 F6 -179.5(8) . . . . ?
F5 C8 C9 C10 -177.2(8) . . . . ?
C7 C8 C9 C10 2.5(14) . . . . ?
F6 C9 C10 C11 178.9(8) . . . . ?
C8 C9 C10 C11 -3.1(13) . . . . ?
F6 C9 C10 I4 -2.4(12) . . . . ?
C8 C9 C10 I4 175.6(7) . . . . ?
C9 C10 C11 C12 2.9(14) . . . . ?
I4 C10 C11 C12 -175.8(7) . . . . ?
C9 C10 C11 F7 178.9(8) . . . . ?
I4 C10 C11 F7 0.2(12) . . . . ?
C10 C11 C12 F8 178.4(8) . . . . ?
F7 C11 C12 F8 2.3(13) . . . . ?
C10 C11 C12 C7 -2.2(14) . . . . ?
F7 C11 C12 C7 -178.3(8) . . . . ?
C8 C7 C12 C11 1.4(13) . . . . ?
I3 C7 C12 C11 -177.2(7) . . . . ?
C8 C7 C12 F8 -179.2(8) . . . . ?
I3 C7 C12 F8 2.1(11) . . . . ?
O1 C13 C14 O2 170.0(10) . . . . ?
O2 C15 C16 O3 83.4(14) . . . . ?
O3 C17 C18 O4 60.5(12) . . . . ?
O4 C19 C20 O5 -72.2(13) . . . . ?
O5 C21 C22 O1 72.2(13) . . . . ?
C32 O6 C23 C24 -88.5(14) . . . . ?
C23 O6 C32 C31 128.4(12) . . . . ?
C25 O7 C24 C23 178.6(12) . . . . ?
O6 C23 C24 O7 72.6(15) . . . . ?
C30 O10 C31 C32 -172.9(12) . . . . ?
O6 C32 C31 O10 168.7(11) . . . . ?
C28 O9 C29 C30 -162.0(15) . . . . ?
C31 O10 C30 C29 -86.5(15) . . . . ?
O9 C29 C30 O10 76.4(17) . . . . ?
C29 O9 C28 C27 89(2) . . . . ?
O9 C28 C27 O8 60(3) . . . . ?
C26 O8 C27 C28 -177.8(18) . . . . ?
C24 O7 C25 C26 156.7(19) . . . . ?
C27 O8 C26 C25 166.4(17) . . . . ?
O7 C25 C26 O8 -71(3) . . . . ?
C21 C22 O1 C13 -93.0(13) . . . . ?
C14 C13 O1 C22 117.1(12) . . . . ?
C16 C15 O2 C14 -80.7(14) . . . . ?
C13 C14 O2 C15 -172.5(11) . . . . ?
C15 C16 O3 C17 -167.7(10) . . . . ?
C18 C17 O3 C16 89.3(11) . . . . ?
C17 C18 O4 C19 178.3(9) . . . . ?
C20 C19 O4 C18 160.8(10) . . . . ?
C19 C20 O5 C21 169.1(9) . . . . ?
C22 C21 O5 C20 -179.5(9) . . . . ?



_diffrn_measured_fraction_theta_max 0.998

_diffrn_reflns_theta_full        25.50

_diffrn_measured_fraction_theta_full 0.998

_refine_diff_density_max         3.143

_refine_diff_density_min         -2.266

_refine_diff_density_rms         0.125

# start Validation Reply Form
_vrf_PLAT431_C5-I14              
;
PROBLEM: Short Inter HL..A Contact I3 ..O1 . 2.95 Ang.
RESPONSE: The Checkcif software has a bug and cannot identify the halogen bond.
;
# end Validation Reply Form

####################################################################### 
# 
# 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_C6-I12-W
_database_code_depnum_ccdc_archive 'CCDC 2281929'
loop_
_audit_author_name
_audit_author_address
'Weizhou Wang'
;Luoyang Normal University
China
;
_audit_update_record             
;
2023-07-17 deposited with the CCDC.	2024-09-11 downloaded from the CCDC.
;



_audit_creation_method           SHELXL-97

_chemical_name_systematic        
;

 ?

;

_chemical_name_common            ?

_chemical_melting_point          ?

_chemical_formula_moiety         ?

_chemical_formula_sum            'C24 H32 F8 I4 O10'

_chemical_formula_weight         1140.10



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'



_symmetry_cell_setting           Triclinic

_symmetry_space_group_name_H-M   P-1



loop_

_symmetry_equiv_pos_as_xyz


'x, y, z'
'-x, -y, -z'



_cell_length_a                   7.6327(5)

_cell_length_b                   8.0627(6)

_cell_length_c                   15.0373(12)

_cell_angle_alpha                88.107(6)

_cell_angle_beta                 77.223(6)

_cell_angle_gamma                89.966(6)

_cell_volume                     901.97(12)

_cell_formula_units_Z            1

_cell_measurement_temperature    295(2)

_cell_measurement_reflns_used    2231

_cell_measurement_theta_min      3.8260

_cell_measurement_theta_max      27.9400



_exptl_crystal_description       block

_exptl_crystal_colour            colourless

_exptl_crystal_size_max          0.40

_exptl_crystal_size_mid          0.40

_exptl_crystal_size_min          0.20

_exptl_crystal_density_meas      ?

_exptl_crystal_density_diffrn    2.099

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             540

_exptl_absorpt_coefficient_mu    3.543

_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.3315

_exptl_absorpt_correction_T_max  0.5376

_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;


_exptl_special_details           
;

 ?

;



_diffrn_ambient_temperature      295(2)

_diffrn_radiation_wavelength     0.71073

_diffrn_radiation_type           MoK\a

_diffrn_radiation_source         'Enhance (Mo) X-ray Source'

_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'

_diffrn_detector_area_resol_mean 16.2542

_diffrn_measurement_method       'phi and omega scans'

_diffrn_standards_number         0

_diffrn_standards_interval_count ?

_diffrn_standards_interval_time  ?

_diffrn_standards_decay_%        ?

_diffrn_reflns_number            5889

_diffrn_reflns_av_R_equivalents  0.0312

_diffrn_reflns_av_sigmaI/netI    0.0521

_diffrn_reflns_limit_h_min       -9

_diffrn_reflns_limit_h_max       9

_diffrn_reflns_limit_k_min       -9

_diffrn_reflns_limit_k_max       7

_diffrn_reflns_limit_l_min       -18

_diffrn_reflns_limit_l_max       18

_diffrn_reflns_theta_min         3.33

_diffrn_reflns_theta_max         25.50

_reflns_number_total             3348

_reflns_number_gt                2617

_reflns_threshold_expression     >2sigma(I)



_computing_data_collection       'Bruker FRAMBO'

_computing_cell_refinement       'Bruker FRAMBO'

_computing_data_reduction        'Bruker SAINT'

_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

_computing_molecular_graphics    'Bruker SHELXTL'

_computing_publication_material  'Bruker SHELXTL'



_refine_special_details          
;

 Refinement of F² against ALL reflections.  The weighted R-factor wR and

 goodness of fit S are based on F², conventional R-factors R are based

 on F, with F set to zero for negative F². The threshold expression of

 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is

 not relevant to the choice of reflections for refinement.  R-factors based

 on F² are statistically about twice as large as those based on F, and R-

 factors based on ALL data will be even larger.

;



_refine_ls_structure_factor_coef Fsqd

_refine_ls_matrix_type           full

_refine_ls_weighting_scheme      calc

_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0291P)²+1.2955P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_primary     direct

_atom_sites_solution_secondary   difmap

_atom_sites_solution_hydrogens   geom

_refine_ls_hydrogen_treatment    constr

_refine_ls_extinction_method     SHELXL

_refine_ls_extinction_coef       0.0310(7)

_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^

_refine_ls_number_reflns         3348

_refine_ls_number_parameters     209

_refine_ls_number_restraints     2

_refine_ls_R_factor_all          0.0601

_refine_ls_R_factor_gt           0.0419

_refine_ls_wR_factor_ref         0.0957

_refine_ls_wR_factor_gt          0.0885

_refine_ls_goodness_of_fit_ref   1.110

_refine_ls_restrained_S_all      1.110

_refine_ls_shift/su_max          0.090

_refine_ls_shift/su_mean         0.003



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_symmetry_multiplicity

_atom_site_calc_flag

_atom_site_refinement_flags

_atom_site_disorder_assembly

_atom_site_disorder_group







































C1 C 0.2763(6) 0.5695(7) 0.4732(4) 0.0413(13) Uani 1 1 d . . .
C2 C 0.2597(6) 0.5950(7) 0.5658(4) 0.0436(13) Uani 1 1 d . . .
C3 C 0.1913(7) 0.4667(8) 0.6263(4) 0.0522(16) Uani 1 1 d . . .
C4 C 0.1423(7) 0.3181(8) 0.5996(5) 0.0550(16) Uani 1 1 d . . .
C5 C 0.1563(7) 0.2939(7) 0.5086(5) 0.0544(16) Uani 1 1 d . . .
C6 C 0.2235(7) 0.4209(7) 0.4468(4) 0.0462(14) Uani 1 1 d . . .
C7 C 0.8131(8) 0.7543(8) 0.8331(4) 0.0612(17) Uani 1 1 d . . .
H7A H 0.8613 0.6880 0.7807 0.073 Uiso 1 1 calc R . .
H7B H 0.8463 0.7025 0.8861 0.073 Uiso 1 1 calc R . .
C8 C 0.5368(9) 0.6052(8) 0.8692(5) 0.0643(18) Uani 1 1 d . . .
H8A H 0.5837 0.5481 0.9167 0.077 Uiso 1 1 calc R . .
H8B H 0.5593 0.5372 0.8159 0.077 Uiso 1 1 calc R . .
C9 C 0.3422(9) 0.6318(8) 0.9010(4) 0.0613(17) Uani 1 1 d . . .
H9A H 0.2985 0.7008 0.8566 0.074 Uiso 1 1 calc R . .
H9B H 0.2792 0.5262 0.9075 0.074 Uiso 1 1 calc R . .
C10 C 0.1239(8) 0.7460(8) 1.0200(5) 0.0670(19) Uani 1 1 d . . .
H10A H 0.0543 0.6442 1.0251 0.080 Uiso 1 1 calc R . .
H10B H 0.0831 0.8210 0.9771 0.080 Uiso 1 1 calc R . .
C11 C 0.0937(8) 0.8225(8) 1.1103(5) 0.0673(19) Uani 1 1 d . . .
H11A H -0.0336 0.8210 1.1384 0.081 Uiso 1 1 calc R . .
H11B H 0.1558 0.7595 1.1498 0.081 Uiso 1 1 calc R . .
C12 C 0.1114(8) 1.0763(9) 1.1826(4) 0.0629(18) Uani 1 1 d . . .
H12A H 0.1585 1.0187 1.2298 0.075 Uiso 1 1 calc R . .
H12B H -0.0183 1.0812 1.2026 0.075 Uiso 1 1 calc R . .
F1 F 0.1721(5) 0.4842(5) 0.7169(2) 0.0784(12) Uani 1 1 d . . .
F2 F 0.0810(5) 0.1948(5) 0.6593(3) 0.0879(13) Uani 1 1 d . . .
F3 F 0.1092(5) 0.1499(5) 0.4791(3) 0.0828(12) Uani 1 1 d . . .
F4 F 0.2353(5) 0.3919(5) 0.3580(2) 0.0691(10) Uani 1 1 d . . .
I1 I 0.38193(5) 0.74760(5) 0.37020(3) 0.05378(13) Uani 1 1 d . . .
I2 I 0.33585(6) 0.81143(6) 0.61884(3) 0.06968(15) Uani 1 1 d . . .
O1 O 0.6230(5) 0.7614(5) 0.8472(3) 0.0520(10) Uani 1 1 d . . .
O2 O 0.3079(5) 0.7107(5) 0.9868(3) 0.0535(10) Uani 1 1 d . . .
O3 O 0.1585(5) 0.9890(5) 1.0996(3) 0.0536(10) Uani 1 1 d . . .
O4 O 0.4419(6) 0.0308(5) 0.7782(3) 0.0676(12) Uani 1 1 d D . .
H1W H 0.4875 -0.0656 0.7767 0.101 Uiso 1 1 d RD . .
H2W H 0.4225 0.0759 0.8297 0.101 Uiso 1 1 d RD . .
O5 O 0.6233(6) 0.8224(5) 0.0526(3) 0.0646(12) Uani 1 1 d . . .
H4W H 0.6878 0.8964 0.0013 0.097 Uiso 1 1 d R . .
H3W H 0.5046 0.7671 0.0435 0.097 Uiso 1 1 d R . .






_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 C6 1.364(8) . ?
C1 C2 1.392(8) . ?
C1 I1 2.101(5) . ?
C2 C3 1.378(8) . ?
C2 I2 2.078(6) . ?
C3 C4 1.355(9) . ?
C3 F1 1.349(7) . ?
C4 F2 1.330(7) . ?
C4 C5 1.368(9) . ?
C5 F3 1.334(7) . ?
C5 C6 1.379(8) . ?
C6 F4 1.346(6) . ?
C7 O1 1.421(7) . ?
C7 C12 1.474(9) 2_677 ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 O1 1.416(7) . ?
C8 C9 1.475(9) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 O2 1.428(7) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 O2 1.414(7) . ?
C10 C11 1.482(9) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 O3 1.423(7) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 O3 1.429(7) . ?
C12 C7 1.474(9) 2_677 ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
O4 H1W 0.8508 . ?
O4 H2W 0.8497 . ?
O5 H4W 0.9980 . ?
O5 H3W 1.0475 . ?



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 C1 C2 119.0(5) . . ?
C6 C1 I1 117.4(4) . . ?
C2 C1 I1 123.6(4) . . ?
C3 C2 C1 117.7(5) . . ?
C3 C2 I2 117.8(4) . . ?
C1 C2 I2 124.5(4) . . ?
C4 C3 F1 116.6(5) . . ?
C4 C3 C2 123.1(6) . . ?
F1 C3 C2 120.4(6) . . ?
F2 C4 C3 121.8(6) . . ?
F2 C4 C5 119.0(6) . . ?
C3 C4 C5 119.2(6) . . ?
F3 C5 C4 121.3(6) . . ?
F3 C5 C6 119.9(6) . . ?
C4 C5 C6 118.8(6) . . ?
F4 C6 C1 120.9(5) . . ?
F4 C6 C5 116.9(5) . . ?
C1 C6 C5 122.2(6) . . ?
O1 C7 C12 109.5(5) . 2_677 ?
O1 C7 H7A 109.8 . . ?
C12 C7 H7A 109.8 2_677 . ?
O1 C7 H7B 109.8 . . ?
C12 C7 H7B 109.8 2_677 . ?
H7A C7 H7B 108.2 . . ?
O1 C8 C9 108.7(5) . . ?
O1 C8 H8A 109.9 . . ?
C9 C8 H8A 109.9 . . ?
O1 C8 H8B 109.9 . . ?
C9 C8 H8B 109.9 . . ?
H8A C8 H8B 108.3 . . ?
O2 C9 C8 109.7(5) . . ?
O2 C9 H9A 109.7 . . ?
C8 C9 H9A 109.7 . . ?
O2 C9 H9B 109.7 . . ?
C8 C9 H9B 109.7 . . ?
H9A C9 H9B 108.2 . . ?
O2 C10 C11 111.1(5) . . ?
O2 C10 H10A 109.4 . . ?
C11 C10 H10A 109.4 . . ?
O2 C10 H10B 109.4 . . ?
C11 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
O3 C11 C10 109.6(5) . . ?
O3 C11 H11A 109.7 . . ?
C10 C11 H11A 109.7 . . ?
O3 C11 H11B 109.7 . . ?
C10 C11 H11B 109.7 . . ?
H11A C11 H11B 108.2 . . ?
O3 C12 C7 109.1(5) . 2_677 ?
O3 C12 H12A 109.9 . . ?
C7 C12 H12A 109.9 2_677 . ?
O3 C12 H12B 109.9 . . ?
C7 C12 H12B 109.9 2_677 . ?
H12A C12 H12B 108.3 . . ?
C8 O1 C7 113.7(5) . . ?
C10 O2 C9 112.9(5) . . ?
C11 O3 C12 112.2(5) . . ?
H1W O4 H2W 115.4 . . ?
H4W O5 H3W 116.0 . . ?



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 0.5(7) . . . . ?
I1 C1 C2 C3 -178.8(4) . . . . ?
C6 C1 C2 I2 179.2(4) . . . . ?
I1 C1 C2 I2 -0.1(6) . . . . ?
C1 C2 C3 C4 0.8(8) . . . . ?
I2 C2 C3 C4 -177.9(4) . . . . ?
C1 C2 C3 F1 180.0(4) . . . . ?
I2 C2 C3 F1 1.2(7) . . . . ?
F1 C3 C4 F2 -1.0(8) . . . . ?
C2 C3 C4 F2 178.3(5) . . . . ?
F1 C3 C4 C5 179.0(5) . . . . ?
C2 C3 C4 C5 -1.7(9) . . . . ?
F2 C4 C5 F3 0.2(8) . . . . ?
C3 C4 C5 F3 -179.8(5) . . . . ?
F2 C4 C5 C6 -178.7(5) . . . . ?
C3 C4 C5 C6 1.3(8) . . . . ?
C2 C1 C6 F4 179.2(5) . . . . ?
I1 C1 C6 F4 -1.5(6) . . . . ?
C2 C1 C6 C5 -0.9(8) . . . . ?
I1 C1 C6 C5 178.4(4) . . . . ?
F3 C5 C6 F4 1.0(8) . . . . ?
C4 C5 C6 F4 179.9(5) . . . . ?
F3 C5 C6 C1 -178.9(5) . . . . ?
C4 C5 C6 C1 0.0(8) . . . . ?
O1 C8 C9 O2 -68.1(6) . . . . ?
O2 C10 C11 O3 73.2(7) . . . . ?
C9 C8 O1 C7 168.2(5) . . . . ?
C12 C7 O1 C8 -175.8(5) 2_677 . . . ?
C11 C10 O2 C9 178.1(5) . . . . ?
C8 C9 O2 C10 177.8(5) . . . . ?
C10 C11 O3 C12 172.1(5) . . . . ?
C7 C12 O3 C11 178.5(5) 2_677 . . . ?



loop_

_geom_hbond_atom_site_label_D

_geom_hbond_atom_site_label_H

_geom_hbond_atom_site_label_A

_geom_hbond_distance_DH

_geom_hbond_distance_HA

_geom_hbond_distance_DA

_geom_hbond_angle_DHA

_geom_hbond_site_symmetry_A




O5 H3W O2 1.05 1.94 2.950(6) 159.8 1_554
O5 H4W O3 1.00 1.91 2.900(6) 170.6 2_676
O4 H2W O5 0.85 1.94 2.787(6) 179.6 2_666
O4 H1W O1 0.85 2.13 2.862(6) 144.4 1_545



_diffrn_measured_fraction_theta_max 0.995

_diffrn_reflns_theta_full        25.50

_diffrn_measured_fraction_theta_full 0.995

_refine_diff_density_max         0.631

_refine_diff_density_min         -0.976

_refine_diff_density_rms         0.102

####################################################################### 
# 
# 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_C4-I14
_database_code_depnum_ccdc_archive 'CCDC 2281928'
loop_
_audit_author_name
_audit_author_address
'Weizhou Wang'
;Luoyang Normal University
China
;
_audit_update_record             
;
2023-07-17 deposited with the CCDC.	2024-09-11 downloaded from the CCDC.
;



_audit_creation_method           SHELXL-97

_chemical_name_systematic        
;

 ?

;

_chemical_name_common            ?

_chemical_melting_point          ?

_chemical_formula_moiety         ?

_chemical_formula_sum            'C10 H8 F4 I2 O2'

_chemical_formula_weight         489.96



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'



_symmetry_cell_setting           Triclinic

_symmetry_space_group_name_H-M   P-1



loop_

_symmetry_equiv_pos_as_xyz


'x, y, z'
'-x, -y, -z'



_cell_length_a                   7.5395(6)

_cell_length_b                   8.6077(7)

_cell_length_c                   12.2413(10)

_cell_angle_alpha                94.007(7)

_cell_angle_beta                 103.778(7)

_cell_angle_gamma                113.576(7)

_cell_volume                     694.90(10)

_cell_formula_units_Z            2

_cell_measurement_temperature    293(2)

_cell_measurement_reflns_used    2010

_cell_measurement_theta_min      3.7200

_cell_measurement_theta_max      26.2470



_exptl_crystal_description       block

_exptl_crystal_colour            yellow

_exptl_crystal_size_max          0.18

_exptl_crystal_size_mid          0.15

_exptl_crystal_size_min          0.11

_exptl_crystal_density_meas      ?

_exptl_crystal_density_diffrn    2.342

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             452

_exptl_absorpt_coefficient_mu    4.562

_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.4939

_exptl_absorpt_correction_T_max  0.6338

_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;



_exptl_special_details           
;

 ?

;



_diffrn_ambient_temperature      293(2)

_diffrn_radiation_wavelength     0.71073

_diffrn_radiation_type           MoK\a

_diffrn_radiation_source         'Enhance (Mo) X-ray Source'

_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'

_diffrn_detector_area_resol_mean 16.2542

_diffrn_measurement_method       'phi and omega scans'


_diffrn_standards_number         ?

_diffrn_standards_interval_count ?

_diffrn_standards_interval_time  ?

_diffrn_standards_decay_%        ?

_diffrn_reflns_number            5112

_diffrn_reflns_av_R_equivalents  0.0317

_diffrn_reflns_av_sigmaI/netI    0.0551

_diffrn_reflns_limit_h_min       -9

_diffrn_reflns_limit_h_max       9

_diffrn_reflns_limit_k_min       -10

_diffrn_reflns_limit_k_max       10

_diffrn_reflns_limit_l_min       -15

_diffrn_reflns_limit_l_max       15

_diffrn_reflns_theta_min         3.41

_diffrn_reflns_theta_max         26.37

_reflns_number_total             2833

_reflns_number_gt                2117

_reflns_threshold_expression     >2sigma(I)



_computing_data_collection       'Bruker FRAMBO'

_computing_cell_refinement       'Bruker FRAMBO'

_computing_data_reduction        'Bruker SAINT'

_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

_computing_molecular_graphics    'Bruker SHELXTL'

_computing_publication_material  'Bruker SHELXTL'



_refine_special_details          
;

 Refinement of F² against ALL reflections.  The weighted R-factor wR and

 goodness of fit S are based on F², conventional R-factors R are based

 on F, with F set to zero for negative F². The threshold expression of

 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is

 not relevant to the choice of reflections for refinement.  R-factors based

 on F² are statistically about twice as large as those based on F, and R-

 factors based on ALL data will be even larger.

;



_refine_ls_structure_factor_coef Fsqd

_refine_ls_matrix_type           full

_refine_ls_weighting_scheme      calc

_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0359P)²+0.0000P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_primary     direct

_atom_sites_solution_secondary   difmap

_atom_sites_solution_hydrogens   geom

_refine_ls_hydrogen_treatment    constr

_refine_ls_extinction_method     SHELXL

_refine_ls_extinction_coef       0.0593(18)

_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^

_refine_ls_number_reflns         2833

_refine_ls_number_parameters     164

_refine_ls_number_restraints     0

_refine_ls_R_factor_all          0.0609

_refine_ls_R_factor_gt           0.0410

_refine_ls_wR_factor_ref         0.0966

_refine_ls_wR_factor_gt          0.0819

_refine_ls_goodness_of_fit_ref   1.056

_refine_ls_restrained_S_all      1.056

_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_symmetry_multiplicity

_atom_site_calc_flag

_atom_site_refinement_flags

_atom_site_disorder_assembly

_atom_site_disorder_group


























C1 C 0.5835(8) 0.5848(8) 0.9219(4) 0.0460(14) Uani 1 1 d . . .
C2 C 0.4656(8) 0.4102(8) 0.8912(4) 0.0464(14) Uani 1 1 d . . .
C3 C 0.3812(9) 0.3270(8) 0.9706(5) 0.0513(15) Uani 1 1 d . . .
C4 C 0.0665(8) 0.5843(8) 0.9133(4) 0.0475(14) Uani 1 1 d . . .
C5 C -0.0286(8) 0.4080(8) 0.8977(4) 0.0491(15) Uani 1 1 d . . .
C6 C -0.0946(9) 0.3259(8) 0.9819(5) 0.0532(15) Uani 1 1 d . . .
C7 C 0.8602(8) 0.1705(9) 0.5057(5) 0.0642(19) Uani 1 1 d . . .
H7A H 0.9520 0.2823 0.5532 0.077 Uiso 1 1 calc R . .
H7B H 0.9370 0.1307 0.4672 0.077 Uiso 1 1 calc R . .
C8 C 0.6470(9) 0.3149(8) 0.4619(5) 0.0627(18) Uani 1 1 d . . .
H8A H 0.7092 0.4196 0.4332 0.075 Uiso 1 1 calc R . .
H8B H 0.6943 0.3423 0.5449 0.075 Uiso 1 1 calc R . .
C9 C 0.4222(10) 0.2502(9) 0.4228(5) 0.0626(18) Uani 1 1 d . . .
H9A H 0.3872 0.3457 0.4339 0.075 Uiso 1 1 calc R . .
H9B H 0.3725 0.2014 0.3417 0.075 Uiso 1 1 calc R . .
C10 C 0.2222(9) -0.0470(8) 0.4199(5) 0.0564(16) Uani 1 1 d . . .
H10A H 0.3129 -0.0776 0.3884 0.068 Uiso 1 1 calc R . .
H10B H 0.1124 -0.0530 0.3568 0.068 Uiso 1 1 calc R . .
F1 F 0.6706(5) 0.6730(5) 0.8481(3) 0.0659(10) Uani 1 1 d . . .
F2 F 0.2627(6) 0.1576(5) 0.9458(3) 0.0801(12) Uani 1 1 d . . .
F3 F -0.0560(6) 0.3133(5) 0.7980(3) 0.0756(12) Uani 1 1 d . . .
F4 F -0.1875(7) 0.1518(5) 0.9592(4) 0.0896(14) Uani 1 1 d . . .
I1 I 0.41135(6) 0.27600(6) 0.72918(3) 0.0594(2) Uani 1 1 d . . .
I2 I 0.16497(7) 0.70805(7) 0.78425(4) 0.0684(2) Uani 1 1 d . . .
O1 O 0.7053(6) 0.1887(6) 0.4221(3) 0.0573(11) Uani 1 1 d . . .
O2 O 0.3275(6) 0.1220(5) 0.4844(3) 0.0529(11) 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 F1 1.344(6) . ?
C1 C2 1.372(8) . ?
C1 C3 1.383(8) 2_667 ?
C2 C3 1.374(7) . ?
C2 I1 2.086(5) . ?
C3 F2 1.335(7) . ?
C3 C1 1.383(8) 2_667 ?
C4 C6 1.374(8) 2_567 ?
C4 C5 1.369(9) . ?
C4 I2 2.084(5) . ?
C5 F3 1.343(6) . ?
C5 C6 1.370(8) . ?
C6 F4 1.350(7) . ?
C6 C4 1.374(8) 2_567 ?
C7 O1 1.427(7) . ?
C7 C10 1.491(8) 2_656 ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 O1 1.421(7) . ?
C8 C9 1.494(8) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 O2 1.428(7) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 O2 1.410(7) . ?
C10 C7 1.491(8) 2_656 ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?



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












































F1 C1 C2 120.3(5) . . ?
F1 C1 C3 118.6(5) . 2_667 ?
C2 C1 C3 121.1(5) . 2_667 ?
C3 C2 C1 117.6(5) . . ?
C3 C2 I1 121.0(5) . . ?
C1 C2 I1 121.4(4) . . ?
F2 C3 C2 120.7(5) . . ?
F2 C3 C1 118.0(5) . 2_667 ?
C2 C3 C1 121.3(6) . 2_667 ?
C6 C4 C5 116.7(5) 2_567 . ?
C6 C4 I2 122.1(5) 2_567 . ?
C5 C4 I2 121.2(4) . . ?
F3 C5 C4 119.4(5) . . ?
F3 C5 C6 119.1(6) . . ?
C4 C5 C6 121.5(5) . . ?
F4 C6 C4 120.6(5) . 2_567 ?
F4 C6 C5 117.7(5) . . ?
C4 C6 C5 121.8(6) 2_567 . ?
O1 C7 C10 112.5(5) . 2_656 ?
O1 C7 H7A 109.1 . . ?
C10 C7 H7A 109.1 2_656 . ?
O1 C7 H7B 109.1 . . ?
C10 C7 H7B 109.1 2_656 . ?
H7A C7 H7B 107.8 . . ?
O1 C8 C9 110.6(5) . . ?
O1 C8 H8A 109.5 . . ?
C9 C8 H8A 109.5 . . ?
O1 C8 H8B 109.5 . . ?
C9 C8 H8B 109.5 . . ?
H8A C8 H8B 108.1 . . ?
O2 C9 C8 111.2(5) . . ?
O2 C9 H9A 109.4 . . ?
C8 C9 H9A 109.4 . . ?
O2 C9 H9B 109.4 . . ?
C8 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
O2 C10 C7 109.8(5) . 2_656 ?
O2 C10 H10A 109.7 . . ?
C7 C10 H10A 109.7 2_656 . ?
O2 C10 H10B 109.7 . . ?
C7 C10 H10B 109.7 2_656 . ?
H10A C10 H10B 108.2 . . ?
C8 O1 C7 113.9(5) . . ?
C10 O2 C9 114.5(4) . . ?



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





















F1 C1 C2 C3 179.8(5) . . . . ?
C3 C1 C2 C3 1.1(10) 2_667 . . . ?
F1 C1 C2 I1 -1.4(8) . . . . ?
C3 C1 C2 I1 179.9(4) 2_667 . . . ?
C1 C2 C3 F2 179.1(6) . . . . ?
I1 C2 C3 F2 0.2(8) . . . . ?
C1 C2 C3 C1 -1.1(10) . . . 2_667 ?
I1 C2 C3 C1 -179.9(4) . . . 2_667 ?
C6 C4 C5 F3 -178.5(5) 2_567 . . . ?
I2 C4 C5 F3 1.0(8) . . . . ?
C6 C4 C5 C6 0.8(10) 2_567 . . . ?
I2 C4 C5 C6 -179.7(4) . . . . ?
F3 C5 C6 F4 -1.0(9) . . . . ?
C4 C5 C6 F4 179.7(6) . . . . ?
F3 C5 C6 C4 178.5(5) . . . 2_567 ?
C4 C5 C6 C4 -0.8(11) . . . 2_567 ?
O1 C8 C9 O2 73.1(7) . . . . ?
C9 C8 O1 C7 -137.4(5) . . . . ?
C10 C7 O1 C8 86.5(7) 2_656 . . . ?
C7 C10 O2 C9 176.8(5) 2_656 . . . ?
C8 C9 O2 C10 -108.5(6) . . . . ?



_diffrn_measured_fraction_theta_max 0.997

_diffrn_reflns_theta_full        26.37

_diffrn_measured_fraction_theta_full 0.997

_refine_diff_density_max         0.675

_refine_diff_density_min         -0.940

_refine_diff_density_rms         0.132

# start Validation Reply Form
_vrf_PLAT431_C4-I14              
;
PROBLEM: Short Inter HL..A Contact I2 ..O1 . 2.99 Ang.
RESPONSE: The Checkcif software has a bug and cannot identify the halogen bond.
;
# end Validation Reply Form

####################################################################### 
# 
# 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_C4-I135
_database_code_depnum_ccdc_archive 'CCDC 2281934'
loop_
_audit_author_name
_audit_author_address
'Weizhou Wang'
;Luoyang Normal University
China
;
_audit_update_record             
;
2023-07-17 deposited with the CCDC.	2024-09-11 downloaded from the CCDC.
;
_audit_creation_date             2023-07-17
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 F3 I3, C8 H16 O4'
_chemical_formula_sum            'C14 H16 F3 I3 O4'
_chemical_formula_weight         685.97
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_H-M_alt        'P 1 21/m 1'
_space_group_name_Hall           '-P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'

_cell_length_a                   4.6368(5)
_cell_length_b                   29.139(4)
_cell_length_c                   7.3508(6)
_cell_angle_alpha                90
_cell_angle_beta                 97.411(9)
_cell_angle_gamma                90
_cell_volume                     984.9(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1355
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.6480
_cell_measurement_theta_min      4.1850
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.802
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.40227
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41r (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.313
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             636
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_av_unetI/netI     0.0622
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.837
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            4437
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.837
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.316
_diffrn_reflns_theta_min         3.494
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0584
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.837
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -26.00  34.00   1.00    3.94    --   16.93 -57.00   0.00   60
  2  ω     44.00  70.00   1.00    3.94    --   16.93   0.00 -60.00   26
  3  ω    -41.00  37.00   1.00    3.94    --  -15.84  77.00-120.00   78
  4  ω    -47.00  -9.00   1.00    3.94    --   16.93   0.00 -60.00   38
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0521037000
_diffrn_orient_matrix_UB_12      0.0225420000
_diffrn_orient_matrix_UB_13      -0.0201905000
_diffrn_orient_matrix_UB_21      -0.0100071000
_diffrn_orient_matrix_UB_22      -0.0048007000
_diffrn_orient_matrix_UB_23      -0.0951671000
_diffrn_orient_matrix_UB_31      -0.1449270000
_diffrn_orient_matrix_UB_32      -0.0077847000
_diffrn_orient_matrix_UB_33      0.0004290000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1665
_reflns_number_total             2308
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SIR2004  (Burla et al.,  2007)'
_refine_diff_density_max         0.639
_refine_diff_density_min         -0.801
_refine_diff_density_rms         0.137
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         2308
_refine_ls_number_restraints     11
_refine_ls_R_factor_all          0.0800
_refine_ls_R_factor_gt           0.0531
_refine_ls_restrained_S_all      1.076
_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)+(0.0356P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0957
_refine_ls_wR_factor_ref         0.1101
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
2. Rigid bond restraints
 O1, C1
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
3. Uiso/Uaniso restraints and constraints
I1 \\sim I1A: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
within 2A
Uanis(I1) = Uanis(I1A)
4. Rigid body (RIGU) restrains
 I1, C6, I1A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
5. Others
 Sof(I1A)=1-FVAR(1)
 Sof(I1)=FVAR(1)
6.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.3667(15) 0.35242(6) 0.3461(5) 0.0566(6) Uani 0.92(3) 1 d . U P A 1
I2 I -0.19835(15) 0.250000 0.92476(10) 0.0719(3) Uani 1 2 d S T P . .
F2 F 0.4790(12) 0.250000 0.2590(7) 0.0608(17) Uani 1 2 d S T P . .
F1 F 0.0255(9) 0.33039(15) 0.6916(6) 0.0666(13) Uani 1 1 d . . . . .
O2 O 0.5522(10) 0.43298(17) 0.1537(6) 0.0516(12) Uani 1 1 d . . . . .
O1 O 0.5701(10) 0.47030(18) -0.2215(7) 0.0597(14) Uani 1 1 d . U . . .
C5 C 0.3214(18) 0.250000 0.3983(13) 0.047(3) Uani 1 2 d S T P A .
C6 C 0.2460(12) 0.2914(2) 0.4667(8) 0.0409(16) Uani 1 1 d . . . . .
C7 C 0.0955(12) 0.2909(2) 0.6178(8) 0.0429(16) Uani 1 1 d . . . . .
C8 C 0.0153(17) 0.250000 0.6906(11) 0.042(2) Uani 1 2 d S T P . .
C4 C 0.6975(18) 0.4616(3) 0.2933(11) 0.069(2) Uani 1 1 d . . . . .
H4A H 0.894878 0.450543 0.325310 0.083 Uiso 1 1 calc R U . . .
H4B H 0.599495 0.459321 0.401842 0.083 Uiso 1 1 calc R U . . .
C1 C 0.2935(16) 0.4893(3) -0.2371(13) 0.068(2) Uani 1 1 d . U . . .
H1A H 0.218116 0.487125 -0.120258 0.081 Uiso 1 1 calc R U . . .
H1B H 0.164329 0.472399 -0.327414 0.081 Uiso 1 1 calc R U . . .
C2 C 0.5811(19) 0.4225(3) -0.1684(12) 0.068(2) Uani 1 1 d . . . . .
H2A H 0.686425 0.405208 -0.251313 0.082 Uiso 1 1 calc R U . . .
H2B H 0.385150 0.410329 -0.177254 0.082 Uiso 1 1 calc R U . . .
C3 C 0.7282(17) 0.4172(3) 0.0237(11) 0.070(2) Uani 1 1 d . . . . .
H3A H 0.774577 0.385121 0.046878 0.084 Uiso 1 1 calc R U . . .
H3B H 0.909125 0.434326 0.037601 0.084 Uiso 1 1 calc R U . . .
I1A I 0.302(10) 0.3513(7) 0.364(4) 0.0566(6) Uani 0.08(3) 1 d . U P A 2


_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 C6 2.095(8) . ?
I2 C8 2.093(8) . ?
F2 C5 1.332(9) . ?
F1 C7 1.331(7) . ?
O2 C4 1.422(9) . ?
O2 C3 1.411(8) . ?
O1 C1 1.388(8) . ?
O1 C2 1.445(8) . ?
C5 C6 1.370(7) 4_565 ?
C5 C6 1.370(7) . ?
C6 C7 1.386(8) . ?
C6 I1A 1.93(3) . ?
C7 C8 1.376(8) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C1 1.491(10) 3_665 ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.495(10) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?

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
C3 O2 C4 114.7(6) . . ?
C1 O1 C2 114.0(6) . . ?
F2 C5 C6 118.3(4) . 4_565 ?
F2 C5 C6 118.3(4) . . ?
C6 C5 C6 123.5(8) . 4_565 ?
C5 C6 I1 119.8(5) . . ?
C5 C6 C7 117.6(7) . . ?
C5 C6 I1A 126.9(13) . . ?
C7 C6 I1 122.6(5) . . ?
C7 C6 I1A 115.4(14) . . ?
F1 C7 C6 119.4(6) . . ?
F1 C7 C8 119.9(6) . . ?
C8 C7 C6 120.7(7) . . ?
C7 C8 I2 120.0(4) 4_565 . ?
C7 C8 I2 120.0(4) . . ?
C7 C8 C7 119.8(8) . 4_565 ?
O2 C4 H4A 109.0 . . ?
O2 C4 H4B 109.0 . . ?
O2 C4 C1 112.9(6) . 3_665 ?
H4A C4 H4B 107.8 . . ?
C1 C4 H4A 109.0 3_665 . ?
C1 C4 H4B 109.0 3_665 . ?
O1 C1 C4 110.3(7) . 3_665 ?
O1 C1 H1A 109.6 . . ?
O1 C1 H1B 109.6 . . ?
C4 C1 H1A 109.6 3_665 . ?
C4 C1 H1B 109.6 3_665 . ?
H1A C1 H1B 108.1 . . ?
O1 C2 H2A 109.5 . . ?
O1 C2 H2B 109.5 . . ?
O1 C2 C3 110.5(7) . . ?
H2A C2 H2B 108.1 . . ?
C3 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
O2 C3 C2 111.9(6) . . ?
O2 C3 H3A 109.2 . . ?
O2 C3 H3B 109.2 . . ?
C2 C3 H3A 109.2 . . ?
C2 C3 H3B 109.2 . . ?
H3A C3 H3B 107.9 . . ?

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
I1 C6 C7 F1 -0.6(8) . . . . ?
I1 C6 C7 C8 178.7(5) . . . . ?
F2 C5 C6 I1 2.1(12) . . . . ?
F2 C5 C6 C7 -176.6(7) . . . . ?
F2 C5 C6 I1A 8.3(18) . . . . ?
F1 C7 C8 I2 -3.0(9) . . . . ?
F1 C7 C8 C7 -178.0(4) . . . 4_565 ?
O1 C2 C3 O2 72.3(8) . . . . ?
C5 C6 C7 F1 178.1(7) . . . . ?
C5 C6 C7 C8 -2.6(11) . . . . ?
C6 C5 C6 I1 -178.6(6) 4_565 . . . ?
C6 C5 C6 C7 2.7(14) 4_565 . . . ?
C6 C5 C6 I1A -172.4(14) 4_565 . . . ?
C6 C7 C8 I2 177.7(5) . . . . ?
C6 C7 C8 C7 2.7(13) . . . 4_565 ?
C4 O2 C3 C2 -133.6(7) . . . . ?
C1 O1 C2 C3 -109.1(8) . . . . ?
C2 O1 C1 C4 -179.6(7) . . . 3_665 ?
C3 O2 C4 C1 84.7(8) . . . 3_665 ?
I1A C6 C7 F1 -6.2(13) . . . . ?
I1A C6 C7 C8 173.0(12) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.540
_oxdiff_exptl_absorpt_empirical_full_min 0.495
####################################################################### 
# 
# 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_C6-I14-W
_database_code_depnum_ccdc_archive 'CCDC 2281930'
loop_
_audit_author_name
_audit_author_address
'Weizhou Wang'
;Luoyang Normal University
China
;
_audit_update_record             
;
2023-07-17 deposited with the CCDC.	2024-09-11 downloaded from the CCDC.
;



_audit_creation_method           SHELXL-97

_chemical_name_systematic        
;

 ?

;

_chemical_name_common            ?

_chemical_melting_point          ?

_chemical_formula_moiety         ?

_chemical_formula_sum            'C18 H30 F4 I2 O9'

_chemical_formula_weight         720.22



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'
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'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'



_symmetry_cell_setting           Triclinic

_symmetry_space_group_name_H-M   P-1



loop_

_symmetry_equiv_pos_as_xyz


'x, y, z'
'-x, -y, -z'



_cell_length_a                   7.5332(5)

_cell_length_b                   13.1800(8)

_cell_length_c                   14.1357(8)

_cell_angle_alpha                105.855(5)

_cell_angle_beta                 91.408(5)

_cell_angle_gamma                103.061(5)

_cell_volume                     1309.58(14)

_cell_formula_units_Z            2

_cell_measurement_temperature    295(2)

_cell_measurement_reflns_used    3343

_cell_measurement_theta_min      6.2610

_cell_measurement_theta_max      71.9690




_exptl_crystal_description       block

_exptl_crystal_colour            colourless

_exptl_crystal_size_max          0.23

_exptl_crystal_size_mid          0.15

_exptl_crystal_size_min          0.11

_exptl_crystal_density_meas      ?

_exptl_crystal_density_diffrn    1.826

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             704

_exptl_absorpt_coefficient_mu    19.513

_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.0939

_exptl_absorpt_correction_T_max  0.2227

_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;




_exptl_special_details           
;

 ?

;



_diffrn_ambient_temperature      295(2)

_diffrn_radiation_wavelength     1.54184

_diffrn_radiation_type           CuK\a

_diffrn_radiation_source         'Enhance (Cu) X-ray Source'

_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'

_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 16.2312

_diffrn_standards_number         0

_diffrn_standards_interval_count ?

_diffrn_standards_interval_time  ?

_diffrn_standards_decay_%        ?

_diffrn_reflns_number            9667

_diffrn_reflns_av_R_equivalents  0.0511

_diffrn_reflns_av_sigmaI/netI    0.0712

_diffrn_reflns_limit_h_min       -7

_diffrn_reflns_limit_h_max       9

_diffrn_reflns_limit_k_min       -16

_diffrn_reflns_limit_k_max       13

_diffrn_reflns_limit_l_min       -16

_diffrn_reflns_limit_l_max       17

_diffrn_reflns_theta_min         3.26

_diffrn_reflns_theta_max         72.36

_reflns_number_total             5033

_reflns_number_gt                4062

_reflns_threshold_expression     >2sigma(I)



_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;

_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

_computing_molecular_graphics    'Bruker SHELXTL'

_computing_publication_material  'Bruker SHELXTL'



_refine_special_details          
;

 Refinement of F² against ALL reflections.  The weighted R-factor wR and

 goodness of fit S are based on F², conventional R-factors R are based

 on F, with F set to zero for negative F². The threshold expression of

 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is

 not relevant to the choice of reflections for refinement.  R-factors based

 on F² are statistically about twice as large as those based on F, and R-

 factors based on ALL data will be even larger.

;



_refine_ls_structure_factor_coef Fsqd

_refine_ls_matrix_type           full

_refine_ls_weighting_scheme      calc

_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0919P)²+0.1537P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_primary     direct

_atom_sites_solution_secondary   difmap

_atom_sites_solution_hydrogens   geom

_refine_ls_hydrogen_treatment    constr

_refine_ls_extinction_method     SHELXL

_refine_ls_extinction_coef       0.00259(17)

_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^

_refine_ls_number_reflns         5033

_refine_ls_number_parameters     299

_refine_ls_number_restraints     0

_refine_ls_R_factor_all          0.0677

_refine_ls_R_factor_gt           0.0572

_refine_ls_wR_factor_ref         0.1642

_refine_ls_wR_factor_gt          0.1499

_refine_ls_goodness_of_fit_ref   1.026

_refine_ls_restrained_S_all      1.026

_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_symmetry_multiplicity

_atom_site_calc_flag

_atom_site_refinement_flags

_atom_site_disorder_assembly

_atom_site_disorder_group































































I1 I 0.64910(6) 0.24094(3) 0.43563(3) 0.04846(13) Uani 1 1 d . . .
I2 I 0.02904(6) 0.79080(3) 0.29157(3) 0.03930(12) Uani 1 1 d . . .
F1 F 0.4719(6) 0.1888(3) 0.6284(3) 0.0533(10) Uani 1 1 d . . .
F2 F 0.6403(6) -0.0056(3) 0.3249(3) 0.0554(11) Uani 1 1 d . . .
F3 F -0.1321(6) 0.7905(3) 0.4993(3) 0.0483(10) Uani 1 1 d . . .
F4 F 0.1538(6) 1.0498(3) 0.3423(3) 0.0488(10) Uani 1 1 d . . .
O1 O 0.5462(7) 0.6478(4) 0.9750(4) 0.0555(13) Uani 1 1 d . . .
O2 O 0.4279(8) 0.8427(4) 1.0289(4) 0.0606(14) Uani 1 1 d . . .
O3 O 0.0949(8) 0.8468(5) 0.9213(4) 0.0684(16) Uani 1 1 d . . .
O4 O 0.0296(8) 0.6801(5) 0.7488(4) 0.0654(15) Uani 1 1 d . . .
O5 O 0.2399(8) 0.5589(4) 0.6276(4) 0.0597(14) Uani 1 1 d . . .
O6 O 0.5081(7) 0.5333(4) 0.7667(4) 0.0527(12) Uani 1 1 d . . .
O7 O 0.5169(16) 0.8041(10) 0.8237(8) 0.168(4) Uani 1 1 d . . .
H1W H 0.4907 0.8155 0.8832 0.251 Uiso 1 1 d R . .
H2W H 0.5147 0.7368 0.8088 0.251 Uiso 1 1 d R . .
O8 O 0.0325(8) 0.6117(4) 0.1193(4) 0.0603(15) Uani 1 1 d . . .
H4W H 0.1031 0.6194 0.0744 0.090 Uiso 1 1 d R . .
H3W H -0.0476 0.5518 0.0985 0.090 Uiso 1 1 d R . .
O9 O 0.1577(7) 0.6112(4) 0.9229(4) 0.0542(13) Uani 1 1 d . . .
H5W H 0.1214 0.6696 0.9401 0.081 Uiso 1 1 d R . .
H6W H 0.2723 0.6193 0.9338 0.081 Uiso 1 1 d R . .
C1 C 0.6439(14) 0.7431(8) 1.0461(7) 0.076(3) Uani 1 1 d . . .
H1A H 0.7264 0.7885 1.0142 0.091 Uiso 1 1 calc R . .
H1B H 0.7161 0.7244 1.0937 0.091 Uiso 1 1 calc R . .
C2 C 0.5132(16) 0.8021(8) 1.0965(6) 0.081(3) Uani 1 1 d . . .
H2A H 0.4214 0.7537 1.1212 0.098 Uiso 1 1 calc R . .
H2B H 0.5767 0.8618 1.1522 0.098 Uiso 1 1 calc R . .
C3 C 0.2965(14) 0.9007(8) 1.0680(7) 0.087(3) Uani 1 1 d . . .
H3A H 0.3540 0.9638 1.1223 0.104 Uiso 1 1 calc R . .
H3B H 0.2008 0.8547 1.0928 0.104 Uiso 1 1 calc R . .
C4 C 0.2160(15) 0.9358(9) 0.9871(9) 0.092(3) Uani 1 1 d . . .
H4A H 0.1517 0.9913 1.0156 0.110 Uiso 1 1 calc R . .
H4B H 0.3133 0.9666 0.9520 0.110 Uiso 1 1 calc R . .
C5 C 0.0632(16) 0.8638(8) 0.8274(7) 0.084(3) Uani 1 1 d . . .
H5A H 0.1785 0.8807 0.7991 0.101 Uiso 1 1 calc R . .
H5B H 0.0068 0.9245 0.8350 0.101 Uiso 1 1 calc R . .
C6 C -0.0571(15) 0.7652(9) 0.7621(7) 0.090(3) Uani 1 1 d . . .
H6A H -0.1714 0.7475 0.7910 0.108 Uiso 1 1 calc R . .
H6B H -0.0844 0.7765 0.6989 0.108 Uiso 1 1 calc R . .
C7 C -0.0470(11) 0.5893(8) 0.6645(6) 0.072(3) Uani 1 1 d . . .
H7A H -0.0509 0.6139 0.6059 0.086 Uiso 1 1 calc R . .
H7B H -0.1711 0.5555 0.6741 0.086 Uiso 1 1 calc R . .
C8 C 0.0673(12) 0.5099(7) 0.6516(6) 0.064(2) Uani 1 1 d . . .
H8A H 0.0805 0.4900 0.7122 0.077 Uiso 1 1 calc R . .
H8B H 0.0108 0.4447 0.5992 0.077 Uiso 1 1 calc R . .
C9 C 0.3608(14) 0.4894(7) 0.6068(6) 0.071(3) Uani 1 1 d . . .
H9A H 0.4713 0.5282 0.5861 0.085 Uiso 1 1 calc R . .
H9B H 0.3045 0.4277 0.5510 0.085 Uiso 1 1 calc R . .
C10 C 0.4148(14) 0.4473(7) 0.6871(7) 0.070(2) Uani 1 1 d . . .
H10A H 0.3066 0.4069 0.7084 0.084 Uiso 1 1 calc R . .
H10B H 0.4929 0.3982 0.6631 0.084 Uiso 1 1 calc R . .
C11 C 0.5612(13) 0.4953(8) 0.8435(7) 0.066(2) Uani 1 1 d . . .
H11A H 0.6364 0.4446 0.8193 0.080 Uiso 1 1 calc R . .
H11B H 0.4534 0.4569 0.8668 0.080 Uiso 1 1 calc R . .
C12 C 0.6618(12) 0.5835(8) 0.9235(6) 0.075(3) Uani 1 1 d . . .
H12A H 0.7199 0.5549 0.9690 0.090 Uiso 1 1 calc R . .
H12B H 0.7572 0.6289 0.8980 0.090 Uiso 1 1 calc R . .
C13 C 0.4888(8) 0.0962(5) 0.5638(4) 0.0340(13) Uani 1 1 d . . .
C14 C 0.5595(8) 0.0973(4) 0.4760(4) 0.0323(12) Uani 1 1 d . . .
C15 C 0.5703(8) -0.0010(5) 0.4122(4) 0.0334(13) Uani 1 1 d . . .
C16 C -0.0667(8) 0.8946(4) 0.4984(4) 0.0318(12) Uani 1 1 d . . .
C17 C 0.0120(7) 0.9155(4) 0.4156(4) 0.0250(11) Uani 1 1 d . . .
C18 C 0.0769(9) 1.0239(5) 0.4208(4) 0.0344(13) 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 C14 2.097(5) . ?
I2 C17 2.079(5) . ?
F1 C13 1.345(7) . ?
F2 C15 1.346(6) . ?
F3 C16 1.353(6) . ?
F4 C18 1.354(6) . ?
O1 C1 1.409(10) . ?
O1 C12 1.426(10) . ?
O2 C3 1.417(11) . ?
O2 C2 1.421(11) . ?
O3 C4 1.398(13) . ?
O3 C5 1.429(10) . ?
O4 C6 1.394(11) . ?
O4 C7 1.436(10) . ?
O5 C8 1.409(9) . ?
O5 C9 1.413(11) . ?
O6 C10 1.396(10) . ?
O6 C11 1.400(10) . ?
O7 H1W 0.8500 . ?
O7 H2W 0.8501 . ?
O8 H4W 0.8500 . ?
O8 H3W 0.8500 . ?
O9 H5W 0.8500 . ?
O9 H6W 0.8500 . ?
C1 C2 1.470(14) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.508(16) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.461(15) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.477(13) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.478(12) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.430(13) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.365(8) . ?
C13 C15 1.369(9) 2_656 ?
C14 C15 1.382(8) . ?
C15 C13 1.369(9) 2_656 ?
C16 C18 1.356(8) 2_576 ?
C16 C17 1.390(7) . ?
C17 C18 1.382(7) . ?
C18 C16 1.356(8) 2_576 ?



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 O1 C12 113.1(7) . . ?
C3 O2 C2 115.0(7) . . ?
C4 O3 C5 112.6(8) . . ?
C6 O4 C7 113.8(7) . . ?
C8 O5 C9 114.1(7) . . ?
C10 O6 C11 111.0(6) . . ?
H1W O7 H2W 100.7 . . ?
H4W O8 H3W 109.5 . . ?
H5W O9 H6W 114.8 . . ?
O1 C1 C2 108.9(8) . . ?
O1 C1 H1A 109.9 . . ?
C2 C1 H1A 109.9 . . ?
O1 C1 H1B 109.9 . . ?
C2 C1 H1B 109.9 . . ?
H1A C1 H1B 108.3 . . ?
O2 C2 C1 109.2(7) . . ?
O2 C2 H2A 109.8 . . ?
C1 C2 H2A 109.8 . . ?
O2 C2 H2B 109.8 . . ?
C1 C2 H2B 109.8 . . ?
H2A C2 H2B 108.3 . . ?
O2 C3 C4 108.5(8) . . ?
O2 C3 H3A 110.0 . . ?
C4 C3 H3A 110.0 . . ?
O2 C3 H3B 110.0 . . ?
C4 C3 H3B 110.0 . . ?
H3A C3 H3B 108.4 . . ?
O3 C4 C3 110.0(9) . . ?
O3 C4 H4A 109.7 . . ?
C3 C4 H4A 109.7 . . ?
O3 C4 H4B 109.7 . . ?
C3 C4 H4B 109.7 . . ?
H4A C4 H4B 108.2 . . ?
O3 C5 C6 108.8(8) . . ?
O3 C5 H5A 109.9 . . ?
C6 C5 H5A 109.9 . . ?
O3 C5 H5B 109.9 . . ?
C6 C5 H5B 109.9 . . ?
H5A C5 H5B 108.3 . . ?
O4 C6 C5 109.0(8) . . ?
O4 C6 H6A 109.9 . . ?
C5 C6 H6A 109.9 . . ?
O4 C6 H6B 109.9 . . ?
C5 C6 H6B 109.9 . . ?
H6A C6 H6B 108.3 . . ?
O4 C7 C8 109.0(7) . . ?
O4 C7 H7A 109.9 . . ?
C8 C7 H7A 109.9 . . ?
O4 C7 H7B 109.9 . . ?
C8 C7 H7B 109.9 . . ?
H7A C7 H7B 108.3 . . ?
O5 C8 C7 107.8(7) . . ?
O5 C8 H8A 110.2 . . ?
C7 C8 H8A 110.2 . . ?
O5 C8 H8B 110.2 . . ?
C7 C8 H8B 110.2 . . ?
H8A C8 H8B 108.5 . . ?
O5 C9 C10 117.4(7) . . ?
O5 C9 H9A 108.0 . . ?
C10 C9 H9A 108.0 . . ?
O5 C9 H9B 108.0 . . ?
C10 C9 H9B 108.0 . . ?
H9A C9 H9B 107.2 . . ?
O6 C10 C9 110.0(7) . . ?
O6 C10 H10A 109.7 . . ?
C9 C10 H10A 109.7 . . ?
O6 C10 H10B 109.7 . . ?
C9 C10 H10B 109.7 . . ?
H10A C10 H10B 108.2 . . ?
O6 C11 C12 110.7(8) . . ?
O6 C11 H11A 109.5 . . ?
C12 C11 H11A 109.5 . . ?
O6 C11 H11B 109.5 . . ?
C12 C11 H11B 109.5 . . ?
H11A C11 H11B 108.1 . . ?
O1 C12 C11 111.6(7) . . ?
O1 C12 H12A 109.3 . . ?
C11 C12 H12A 109.3 . . ?
O1 C12 H12B 109.3 . . ?
C11 C12 H12B 109.3 . . ?
H12A C12 H12B 108.0 . . ?
F1 C13 C14 120.6(5) . . ?
F1 C13 C15 118.2(5) . 2_656 ?
C14 C13 C15 121.2(5) . 2_656 ?
C13 C14 C15 117.7(5) . . ?
C13 C14 I1 122.5(4) . . ?
C15 C14 I1 119.8(4) . . ?
F2 C15 C13 118.1(5) . 2_656 ?
F2 C15 C14 120.8(6) . . ?
C13 C15 C14 121.1(5) 2_656 . ?
F3 C16 C18 118.9(5) . 2_576 ?
F3 C16 C17 119.5(5) . . ?
C18 C16 C17 121.6(5) 2_576 . ?
C18 C17 C16 115.9(5) . . ?
C18 C17 I2 122.3(4) . . ?
C16 C17 I2 121.8(4) . . ?
F4 C18 C16 118.7(5) . 2_576 ?
F4 C18 C17 118.9(5) . . ?
C16 C18 C17 122.4(5) 2_576 . ?



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


































C12 O1 C1 C2 -178.7(7) . . . . ?
C3 O2 C2 C1 179.4(7) . . . . ?
O1 C1 C2 O2 -68.1(9) . . . . ?
C2 O2 C3 C4 -178.7(8) . . . . ?
C5 O3 C4 C3 -159.6(8) . . . . ?
O2 C3 C4 O3 74.6(10) . . . . ?
C4 O3 C5 C6 177.2(8) . . . . ?
C7 O4 C6 C5 -161.8(7) . . . . ?
O3 C5 C6 O4 -62.0(10) . . . . ?
C6 O4 C7 C8 174.0(7) . . . . ?
C9 O5 C8 C7 -176.1(7) . . . . ?
O4 C7 C8 O5 -65.7(8) . . . . ?
C8 O5 C9 C10 -62.2(10) . . . . ?
C11 O6 C10 C9 -179.8(7) . . . . ?
O5 C9 C10 O6 -61.9(11) . . . . ?
C10 O6 C11 C12 178.1(8) . . . . ?
C1 O1 C12 C11 -172.4(7) . . . . ?
O6 C11 C12 O1 71.5(9) . . . . ?
F1 C13 C14 C15 -178.9(5) . . . . ?
C15 C13 C14 C15 -0.3(10) 2_656 . . . ?
F1 C13 C14 I1 0.7(8) . . . . ?
C15 C13 C14 I1 179.4(4) 2_656 . . . ?
C13 C14 C15 F2 -179.3(5) . . . . ?
I1 C14 C15 F2 1.0(8) . . . . ?
C13 C14 C15 C13 0.3(10) . . . 2_656 ?
I1 C14 C15 C13 -179.4(5) . . . 2_656 ?
F3 C16 C17 C18 -179.5(5) . . . . ?
C18 C16 C17 C18 -0.6(10) 2_576 . . . ?
F3 C16 C17 I2 0.9(8) . . . . ?
C18 C16 C17 I2 179.7(5) 2_576 . . . ?
C16 C17 C18 F4 -179.4(5) . . . . ?
I2 C17 C18 F4 0.2(8) . . . . ?
C16 C17 C18 C16 0.6(10) . . . 2_576 ?
I2 C17 C18 C16 -179.7(5) . . . 2_576 ?



loop_

_geom_hbond_atom_site_label_D

_geom_hbond_atom_site_label_H

_geom_hbond_atom_site_label_A

_geom_hbond_distance_DH

_geom_hbond_distance_HA

_geom_hbond_distance_DA

_geom_hbond_angle_DHA

_geom_hbond_site_symmetry_A






O7 H1W O2 0.85 2.08 2.927(12) 179.5 .
O7 H2W O6 0.85 2.57 3.422(13) 179.1 .
O8 H4W O9 0.85 2.17 2.953(7) 153.1 1_554
O8 H3W O9 0.85 2.06 2.853(7) 155.9 2_566
O9 H5W O3 0.85 2.47 3.250(8) 152.7 .
O9 H6W O1 0.85 2.05 2.899(7) 174.0 .



_diffrn_measured_fraction_theta_max 0.969

_diffrn_reflns_theta_full        72.36

_diffrn_measured_fraction_theta_full 0.969

_refine_diff_density_max         1.659

_refine_diff_density_min         -2.168

_refine_diff_density_rms         0.164

# start Validation Reply Form
_vrf_PLAT431_C6-I14-W            
;
PROBLEM: Short Inter HL..A Contact I1 ..O5 . 2.96 Ang.
RESPONSE: The Checkcif software has a bug and cannot identify the halogen bond.
;
# end Validation Reply Form


####################################################################### 
# 
# 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_C4-I13
_database_code_depnum_ccdc_archive 'CCDC 2281935'
loop_
_audit_author_name
_audit_author_address
'Weizhou Wang'
;Luoyang Normal University
China
;
_audit_update_record             
;
2023-07-17 deposited with the CCDC.	2024-09-11 downloaded from the CCDC.
;
_audit_creation_date             2023-07-17
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 F4 I2, C4 H8 O2'
_chemical_formula_sum            'C10 H8 F4 I2 O2'
_chemical_formula_weight         489.96
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.0376(4)
_cell_length_b                   15.4508(8)
_cell_length_c                   7.5142(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.120(3)
_cell_angle_gamma                90
_cell_volume                     1391.99(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3459
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      27.0750
_cell_measurement_theta_min      4.2430
_shelx_estimated_absorpt_T_max   0.568
_shelx_estimated_absorpt_T_min   0.494
_exptl_absorpt_coefficient_mu    4.555
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.29783
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41r (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.338
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0561
_diffrn_reflns_av_unetI/netI     0.0580
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.852
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8105
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.852
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.304
_diffrn_reflns_theta_min         3.398
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0584
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.852
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -83.00  56.00   1.00    1.88    --  -13.48   0.00   0.00  139
  2  ω    -20.00  25.00   1.00    1.88    --  -13.48 -99.00   0.00   45
  3  ω    -20.00  25.00   1.00    1.88    --  -13.48 -99.00 150.00   45
  4  ω    -20.00  31.00   1.00    1.88    --   14.49 -99.00-150.00   51
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0293234000
_diffrn_orient_matrix_UB_12      0.0220861000
_diffrn_orient_matrix_UB_13      0.0640743000
_diffrn_orient_matrix_UB_21      0.0004507000
_diffrn_orient_matrix_UB_22      -0.0381166000
_diffrn_orient_matrix_UB_23      0.0526650000
_diffrn_orient_matrix_UB_31      0.0513725000
_diffrn_orient_matrix_UB_32      0.0129339000
_diffrn_orient_matrix_UB_33      0.0458532000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2262
_reflns_number_total             2945
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.860
_refine_diff_density_min         -0.654
_refine_diff_density_rms         0.111
_refine_ls_extinction_coef       0.0331(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2945
_refine_ls_number_restraints     25
_refine_ls_R_factor_all          0.0615
_refine_ls_R_factor_gt           0.0439
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0340P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0858
_refine_ls_wR_factor_ref         0.0949
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
2. Uiso/Uaniso restraints and constraints
I1 \\sim I1A \\sim I1B: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02 within 2A
Uanis(I1) = Uanis(I1A) = Uanis(I1B)
3. Rigid body (RIGU) restrains
 I1, C2, I1A, I1B
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
4. Others
 1*[Sof(I1)]+1*[Sof(I1A)]+1*[Sof(I1B)]=1 with esd of 0
5.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.67926(9) 0.34459(9) 0.1605(2) 0.0595(3) Uani 0.871(3) 1 d . U P A 1
I2 I 0.20142(3) 0.36822(3) -0.17218(5) 0.0591(2) Uani 1 1 d . . . . .
F1 F 0.4452(2) 0.4209(3) -0.0045(5) 0.0817(13) Uani 1 1 d . . . . .
F2 F 0.6068(3) 0.1490(2) 0.1222(5) 0.0761(11) Uani 1 1 d . . . . .
F3 F 0.4207(3) 0.0719(3) -0.0224(6) 0.0972(14) Uani 1 1 d . . . . .
F4 F 0.2468(3) 0.1671(2) -0.1571(5) 0.0722(10) Uani 1 1 d . . . . .
C1 C 0.4398(4) 0.3350(4) -0.0104(7) 0.0469(14) Uani 1 1 d . . . . .
C2 C 0.5313(4) 0.2864(4) 0.0555(7) 0.0470(14) Uani 1 1 d . . . . .
C3 C 0.5227(4) 0.1987(4) 0.0541(7) 0.0512(14) Uani 1 1 d . . . . .
C4 C 0.4272(4) 0.1586(4) -0.0196(8) 0.0547(16) Uani 1 1 d . . . . .
C5 C 0.3390(4) 0.2073(4) -0.0855(7) 0.0478(14) Uani 1 1 d . . . . .
C6 C 0.3414(4) 0.2962(4) -0.0813(6) 0.0412(12) Uani 1 1 d . . . . .
O1 O 0.8986(3) 0.4007(3) 0.3431(5) 0.0584(11) Uani 1 1 d . . . . .
O2 O 0.9754(3) 0.4436(3) 0.7204(5) 0.0556(10) Uani 1 1 d . . . . .
C7 C 1.0175(5) 0.5884(4) 0.7777(8) 0.0666(18) Uani 1 1 d . . . . .
H7A H 0.983505 0.644167 0.797140 0.080 Uiso 1 1 calc R U . . .
H7B H 1.052486 0.568551 0.891701 0.080 Uiso 1 1 calc R U . . .
C8 C 0.9295(4) 0.5267(4) 0.7144(8) 0.0604(16) Uani 1 1 d . . . . .
H8A H 0.868342 0.529593 0.789917 0.072 Uiso 1 1 calc R U . . .
H8B H 0.900969 0.540757 0.593079 0.072 Uiso 1 1 calc R U . . .
C9 C 0.8974(5) 0.3777(4) 0.6568(9) 0.0656(18) Uani 1 1 d . . . . .
H9A H 0.822789 0.401926 0.643874 0.079 Uiso 1 1 calc R U . . .
H9B H 0.898387 0.331311 0.743945 0.079 Uiso 1 1 calc R U . . .
C10 C 0.9245(5) 0.3419(4) 0.4826(8) 0.0637(18) Uani 1 1 d . . . . .
H10A H 1.003380 0.328074 0.488863 0.076 Uiso 1 1 calc R U . . .
H10B H 0.882968 0.288816 0.458251 0.076 Uiso 1 1 calc R U . . .
I1A I 0.6841(14) 0.3641(15) 0.108(3) 0.0595(3) Uani 0.042(3) 1 d . U P A 2
I1B I 0.6641(9) 0.3671(9) 0.1793(18) 0.0595(3) Uani 0.087(3) 1 d . U P A 3


_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 C2 2.086(5) . ?
I2 C6 2.083(5) . ?
F1 C1 1.330(7) . ?
F2 C3 1.336(6) . ?
F3 C4 1.342(7) . ?
F4 C5 1.341(5) . ?
C1 C2 1.387(7) . ?
C1 C6 1.390(7) . ?
C2 C3 1.359(8) . ?
C2 I1A 2.202(18) . ?
C2 I1B 2.170(13) . ?
C3 C4 1.378(7) . ?
C4 C5 1.358(7) . ?
C5 C6 1.373(7) . ?
O1 C7 1.427(7) 3_766 ?
O1 C10 1.400(7) . ?
O2 C8 1.396(7) . ?
O2 C9 1.438(7) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.473(8) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.484(8) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?

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
F1 C1 C2 119.5(4) . . ?
F1 C1 C6 118.7(4) . . ?
C2 C1 C6 121.7(6) . . ?
C1 C2 I1 121.7(4) . . ?
C1 C2 I1A 113.2(7) . . ?
C1 C2 I1B 111.9(5) . . ?
C3 C2 I1 119.6(4) . . ?
C3 C2 C1 118.6(5) . . ?
C3 C2 I1A 127.4(7) . . ?
C3 C2 I1B 129.0(5) . . ?
F2 C3 C2 121.1(5) . . ?
F2 C3 C4 118.2(6) . . ?
C2 C3 C4 120.8(5) . . ?
F3 C4 C3 120.0(5) . . ?
F3 C4 C5 120.3(5) . . ?
C5 C4 C3 119.6(6) . . ?
F4 C5 C4 118.8(5) . . ?
F4 C5 C6 119.2(5) . . ?
C4 C5 C6 122.1(5) . . ?
C1 C6 I2 122.1(4) . . ?
C5 C6 I2 120.7(3) . . ?
C5 C6 C1 117.1(5) . . ?
C10 O1 C7 115.5(5) . 3_766 ?
C8 O2 C9 113.3(4) . . ?
O1 C7 H7A 108.9 3_766 . ?
O1 C7 H7B 108.9 3_766 . ?
O1 C7 C8 113.6(5) 3_766 . ?
H7A C7 H7B 107.7 . . ?
C8 C7 H7A 108.9 . . ?
C8 C7 H7B 108.9 . . ?
O2 C8 C7 108.3(5) . . ?
O2 C8 H8A 110.0 . . ?
O2 C8 H8B 110.0 . . ?
C7 C8 H8A 110.0 . . ?
C7 C8 H8B 110.0 . . ?
H8A C8 H8B 108.4 . . ?
O2 C9 H9A 109.3 . . ?
O2 C9 H9B 109.3 . . ?
O2 C9 C10 111.6(5) . . ?
H9A C9 H9B 108.0 . . ?
C10 C9 H9A 109.3 . . ?
C10 C9 H9B 109.3 . . ?
O1 C10 C9 111.5(5) . . ?
O1 C10 H10A 109.3 . . ?
O1 C10 H10B 109.3 . . ?
C9 C10 H10A 109.3 . . ?
C9 C10 H10B 109.3 . . ?
H10A C10 H10B 108.0 . . ?

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
I1 C2 C3 F2 1.4(7) . . . . ?
I1 C2 C3 C4 -177.9(4) . . . . ?
F1 C1 C2 I1 -1.1(7) . . . . ?
F1 C1 C2 C3 177.7(5) . . . . ?
F1 C1 C2 I1A -12.3(8) . . . . ?
F1 C1 C2 I1B 4.9(7) . . . . ?
F1 C1 C6 I2 -1.6(7) . . . . ?
F1 C1 C6 C5 179.9(5) . . . . ?
F2 C3 C4 F3 -0.3(8) . . . . ?
F2 C3 C4 C5 178.2(5) . . . . ?
F3 C4 C5 F4 -1.6(8) . . . . ?
F3 C4 C5 C6 178.5(5) . . . . ?
F4 C5 C6 I2 3.2(7) . . . . ?
F4 C5 C6 C1 -178.2(4) . . . . ?
C1 C2 C3 F2 -177.4(5) . . . . ?
C1 C2 C3 C4 3.3(8) . . . . ?
C2 C1 C6 I2 177.7(4) . . . . ?
C2 C1 C6 C5 -0.8(8) . . . . ?
C2 C3 C4 F3 179.0(5) . . . . ?
C2 C3 C4 C5 -2.5(8) . . . . ?
C3 C4 C5 F4 179.9(5) . . . . ?
C3 C4 C5 C6 -0.1(8) . . . . ?
C4 C5 C6 I2 -176.9(4) . . . . ?
C4 C5 C6 C1 1.7(8) . . . . ?
C6 C1 C2 I1 179.6(4) . . . . ?
C6 C1 C2 C3 -1.6(8) . . . . ?
C6 C1 C2 I1A 168.4(7) . . . . ?
C6 C1 C2 I1B -174.3(5) . . . . ?
O1 C7 C8 O2 70.0(7) 3_766 . . . ?
O2 C9 C10 O1 -73.1(6) . . . . ?
C7 O1 C10 C9 134.1(5) 3_766 . . . ?
C8 O2 C9 C10 109.5(6) . . . . ?
C9 O2 C8 C7 -178.5(5) . . . . ?
I1A C2 C3 F2 14.1(10) . . . . ?
I1A C2 C3 C4 -165.2(8) . . . . ?
I1B C2 C3 F2 -6.1(9) . . . . ?
I1B C2 C3 C4 174.6(6) . . . . ?

_olex2_date_sample_data_collection 2016-07-21
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.984
_oxdiff_exptl_absorpt_empirical_full_min 0.747
####################################################################### 
# 
# 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_C5-I135
_database_code_depnum_ccdc_archive 'CCDC 2281936'
loop_
_audit_author_name
_audit_author_address
'Weizhou Wang'
;Luoyang Normal University
China
;
_audit_update_record             
;
2023-07-17 deposited with the CCDC.	2024-09-11 downloaded from the CCDC.
;
_audit_creation_date             2016-09-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.08.25 svn.r3337 for OlexSys, GUI svn.r5221)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C10 H20 O5, 2(C6 F3 I3)'
_chemical_formula_sum            'C22 H19 F6 I6 O5'
_chemical_formula_weight         1238.77
_chemical_absolute_configuration ?
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C 1 c 1'
_space_group_name_Hall           'C -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   16.1779(9)
_cell_length_b                   8.4631(4)
_cell_length_c                   25.3518(15)
_cell_angle_alpha                90
_cell_angle_beta                 105.819(6)
_cell_angle_gamma                90
_cell_volume                     3339.6(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4788
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      26.2040
_cell_measurement_theta_min      3.9490
_shelx_estimated_absorpt_T_max   0.333
_shelx_estimated_absorpt_T_min   0.257
_exptl_absorpt_coefficient_mu    5.643
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54554
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41r (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.464
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2252
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.25
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_unetI/netI     0.0404
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            9499
_diffrn_reflns_point_group_measured_fraction_full 0.935
_diffrn_reflns_point_group_measured_fraction_max 0.935
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         3.341
_diffrn_ambient_temperature      295.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0584
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -43.00  52.00   1.00   11.76    --  -15.84  77.00-180.00   95
  2  ω    -45.00  56.00   1.00   11.76    --  -15.84  19.00 120.00  101
  3  ω     35.00  89.00   1.00   11.76    --   16.93 178.00  30.00   54
  4  ω    -83.00 -21.00   1.00   11.76    --  -15.84 -77.00 120.00   62
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0398856000
_diffrn_orient_matrix_UB_12      -0.0039635000
_diffrn_orient_matrix_UB_13      -0.0204196000
_diffrn_orient_matrix_UB_21      0.0165785000
_diffrn_orient_matrix_UB_22      0.0494047000
_diffrn_orient_matrix_UB_23      -0.0173116000
_diffrn_orient_matrix_UB_31      0.0145566000
_diffrn_orient_matrix_UB_32      -0.0675768000
_diffrn_orient_matrix_UB_33      -0.0113586000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.873
_reflns_Friedel_fraction_full    0.872
_reflns_Friedel_fraction_max     0.872
_reflns_number_gt                5002
_reflns_number_total             5483
_reflns_odcompleteness_completeness 99.67
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         0.864
_refine_diff_density_min         -1.030
_refine_diff_density_rms         0.105
_refine_ls_abs_structure_details 
;
 Flack x determined using 1911 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     352
_refine_ls_number_reflns         5483
_refine_ls_number_restraints     63
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0388
_refine_ls_restrained_S_all      1.048
_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)+(0.0465P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0902
_refine_ls_wR_factor_ref         0.0949
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
2. Restrained distances
 C1-C2 \\sim C3-C4 \\sim C5-C6 \\sim C7-C8 \\sim C9-C10
 with sigma of 0.01
 O1-C1 \\sim O2-C2 \\sim O2-C3 \\sim O3-C4 \\sim O3-C5 \\sim O4-C6 \\sim O4-C7
\\sim O5-C8 \\sim O5-C9 \\sim O1-C10
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C4) \\sim Ueq: with sigma of 0.02 and sigma for terminal atoms of 0.04
4.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B),
 C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
O1 O 0.4120(7) 0.7334(12) 0.5479(4) 0.069(3) Uani 1 1 d D . . . .
O2 O 0.2248(9) 0.7898(19) 0.5463(6) 0.117(5) Uani 1 1 d D . . . .
O3 O 0.1073(9) 0.5691(17) 0.4933(6) 0.100(4) Uani 1 1 d D . . . .
O4 O 0.2239(7) 0.3242(14) 0.4836(5) 0.078(3) Uani 1 1 d D . . . .
O5 O 0.3764(8) 0.4226(12) 0.4472(4) 0.072(3) Uani 1 1 d D . . . .
C1 C 0.3678(12) 0.8651(17) 0.5606(9) 0.093(6) Uani 1 1 d D . . . .
H1A H 0.3422 0.9229 0.5271 0.111 Uiso 1 1 calc R . . . .
H1B H 0.4090 0.9346 0.5847 0.111 Uiso 1 1 calc R . . . .
C2 C 0.3003(11) 0.826(2) 0.5869(7) 0.100(7) Uani 1 1 d D . . . .
H2A H 0.3178 0.7364 0.6112 0.120 Uiso 1 1 calc R . . . .
H2B H 0.2904 0.9151 0.6085 0.120 Uiso 1 1 calc R . . . .
C3 C 0.1682(15) 0.725(3) 0.5741(9) 0.130(10) Uani 1 1 d D . . . .
H3A H 0.1526 0.8052 0.5970 0.156 Uiso 1 1 calc R . . . .
H3B H 0.1959 0.6388 0.5973 0.156 Uiso 1 1 calc R . . . .
C4 C 0.0917(16) 0.668(4) 0.5340(10) 0.149(11) Uani 1 1 d D U . . .
H4A H 0.0566 0.6115 0.5531 0.179 Uiso 1 1 calc R . . . .
H4B H 0.0588 0.7588 0.5162 0.179 Uiso 1 1 calc R . . . .
C5 C 0.1004(12) 0.4113(19) 0.5088(8) 0.093(6) Uani 1 1 d D . . . .
H5A H 0.0407 0.3857 0.5052 0.112 Uiso 1 1 calc R . . . .
H5B H 0.1325 0.3964 0.5468 0.112 Uiso 1 1 calc R . . . .
C6 C 0.1344(9) 0.308(3) 0.4736(9) 0.104(7) Uani 1 1 d D . . . .
H6A H 0.1210 0.1991 0.4800 0.125 Uiso 1 1 calc R . . . .
H6B H 0.1068 0.3328 0.4356 0.125 Uiso 1 1 calc R . . . .
C7 C 0.2558(10) 0.251(2) 0.4430(6) 0.074(5) Uani 1 1 d D . . . .
H7A H 0.2294 0.2988 0.4076 0.089 Uiso 1 1 calc R . . . .
H7B H 0.2409 0.1398 0.4407 0.089 Uiso 1 1 calc R . . . .
C8 C 0.3497(9) 0.2682(16) 0.4560(7) 0.073(5) Uani 1 1 d D . . . .
H8A H 0.3748 0.2397 0.4940 0.088 Uiso 1 1 calc R . . . .
H8B H 0.3715 0.1950 0.4335 0.088 Uiso 1 1 calc R . . . .
C9 C 0.4186(10) 0.5105(19) 0.4940(6) 0.075(5) Uani 1 1 d D . . . .
H9A H 0.4730 0.5490 0.4900 0.090 Uiso 1 1 calc R . . . .
H9B H 0.4304 0.4428 0.5261 0.090 Uiso 1 1 calc R . . . .
C10 C 0.3657(10) 0.645(2) 0.5019(6) 0.079(5) Uani 1 1 d D . . . .
H10A H 0.3520 0.7114 0.4695 0.095 Uiso 1 1 calc R . . . .
H10B H 0.3124 0.6073 0.5079 0.095 Uiso 1 1 calc R . . . .
I1 I 0.55227(7) 0.66245(13) 0.64916(4) 0.0728(3) Uani 1 1 d . . . . .
I2 I 0.64049(6) 0.78462(15) 0.89218(4) 0.0722(3) Uani 1 1 d . . . . .
I3 I 0.89287(7) 0.44288(13) 0.79756(7) 0.0950(5) Uani 1 1 d . . . . .
F1 F 0.5420(5) 0.7672(11) 0.7655(3) 0.068(2) Uani 1 1 d . . . . .
F2 F 0.8045(5) 0.5981(11) 0.8809(4) 0.073(2) Uani 1 1 d . . . . .
F3 F 0.7396(7) 0.5177(12) 0.6910(4) 0.082(3) Uani 1 1 d . . . . .
C11 C 0.6392(9) 0.6417(15) 0.7267(5) 0.050(3) Uani 1 1 d . . . . .
C12 C 0.7174(9) 0.5710(16) 0.7350(6) 0.053(3) Uani 1 1 d . . . . .
C13 C 0.7751(8) 0.5569(16) 0.7866(6) 0.052(3) Uani 1 1 d . . . . .
C14 C 0.7514(8) 0.6152(16) 0.8310(6) 0.052(3) Uani 1 1 d . . . . .
C15 C 0.6726(7) 0.6890(15) 0.8247(5) 0.044(3) Uani 1 1 d . . . . .
C16 C 0.6176(8) 0.6989(15) 0.7722(6) 0.051(3) Uani 1 1 d . . . . .
I4 I 0.41251(6) 0.53537(11) 0.34869(4) 0.0587(3) Uani 1 1 d . . . . .
I5 I 0.67005(7) 0.86469(13) 0.25474(6) 0.0864(4) Uani 1 1 d . . . . .
I6 I 0.32466(8) 0.68706(14) 0.10776(5) 0.0778(3) Uani 1 1 d . . . . .
F4 F 0.5844(6) 0.6877(11) 0.3362(4) 0.076(3) Uani 1 1 d . . . . .
F5 F 0.5104(7) 0.8259(11) 0.1503(4) 0.083(3) Uani 1 1 d . . . . .
F6 F 0.3132(5) 0.5650(12) 0.2226(4) 0.075(3) Uani 1 1 d . . . . .
C17 C 0.4475(8) 0.6223(15) 0.2811(5) 0.043(3) Uani 1 1 d . . . . .
C18 C 0.3923(8) 0.6261(16) 0.2309(6) 0.048(3) Uani 1 1 d . . . . .
C19 C 0.4092(9) 0.6933(15) 0.1848(5) 0.050(3) Uani 1 1 d . . . . .
C20 C 0.4918(9) 0.7593(16) 0.1941(6) 0.052(3) Uani 1 1 d . . . . .
C21 C 0.5501(8) 0.7601(16) 0.2431(6) 0.052(3) Uani 1 1 d . . . . .
C22 C 0.5272(9) 0.6936(16) 0.2874(7) 0.055(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
O1 C1 1.409(11) . ?
O1 C10 1.414(11) . ?
O2 C2 1.399(12) . ?
O2 C3 1.409(11) . ?
O3 C4 1.405(12) . ?
O3 C5 1.404(11) . ?
O4 C6 1.407(11) . ?
O4 C7 1.413(11) . ?
O5 C8 1.412(11) . ?
O5 C9 1.409(11) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.463(15) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.453(16) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.459(15) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.471(14) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.470(15) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
I1 C11 2.089(14) . ?
I2 C15 2.082(12) . ?
I3 C13 2.086(12) . ?
F1 C16 1.321(14) . ?
F2 C14 1.330(16) . ?
F3 C12 1.340(15) . ?
C11 C12 1.36(2) . ?
C11 C16 1.381(19) . ?
C12 C13 1.39(2) . ?
C13 C14 1.38(2) . ?
C14 C15 1.388(17) . ?
C15 C16 1.388(19) . ?
I4 C17 2.080(12) . ?
I5 C21 2.080(12) . ?
I6 C19 2.057(13) . ?
F4 C22 1.329(17) . ?
F5 C20 1.350(16) . ?
F6 C18 1.343(14) . ?
C17 C18 1.342(19) . ?
C17 C22 1.393(18) . ?
C18 C19 1.392(18) . ?
C19 C20 1.408(19) . ?
C20 C21 1.34(2) . ?
C21 C22 1.39(2) . ?

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 O1 C10 114.8(12) . . ?
C2 O2 C3 105.9(17) . . ?
C5 O3 C4 108.6(18) . . ?
C6 O4 C7 112.9(12) . . ?
C9 O5 C8 117.1(13) . . ?
O1 C1 H1A 108.6 . . ?
O1 C1 H1B 108.6 . . ?
O1 C1 C2 114.5(15) . . ?
H1A C1 H1B 107.6 . . ?
C2 C1 H1A 108.6 . . ?
C2 C1 H1B 108.6 . . ?
O2 C2 C1 108.9(16) . . ?
O2 C2 H2A 109.9 . . ?
O2 C2 H2B 109.9 . . ?
C1 C2 H2A 109.9 . . ?
C1 C2 H2B 109.9 . . ?
H2A C2 H2B 108.3 . . ?
O2 C3 H3A 109.9 . . ?
O2 C3 H3B 109.9 . . ?
O2 C3 C4 109.0(19) . . ?
H3A C3 H3B 108.3 . . ?
C4 C3 H3A 109.9 . . ?
C4 C3 H3B 109.9 . . ?
O3 C4 C3 115.0(19) . . ?
O3 C4 H4A 108.5 . . ?
O3 C4 H4B 108.5 . . ?
C3 C4 H4A 108.5 . . ?
C3 C4 H4B 108.5 . . ?
H4A C4 H4B 107.5 . . ?
O3 C5 H5A 109.9 . . ?
O3 C5 H5B 109.9 . . ?
O3 C5 C6 109.1(16) . . ?
H5A C5 H5B 108.3 . . ?
C6 C5 H5A 109.9 . . ?
C6 C5 H5B 109.9 . . ?
O4 C6 C5 111.9(14) . . ?
O4 C6 H6A 109.2 . . ?
O4 C6 H6B 109.2 . . ?
C5 C6 H6A 109.2 . . ?
C5 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
O4 C7 H7A 109.5 . . ?
O4 C7 H7B 109.5 . . ?
O4 C7 C8 110.7(13) . . ?
H7A C7 H7B 108.1 . . ?
C8 C7 H7A 109.5 . . ?
C8 C7 H7B 109.5 . . ?
O5 C8 C7 113.4(13) . . ?
O5 C8 H8A 108.9 . . ?
O5 C8 H8B 108.9 . . ?
C7 C8 H8A 108.9 . . ?
C7 C8 H8B 108.9 . . ?
H8A C8 H8B 107.7 . . ?
O5 C9 H9A 109.4 . . ?
O5 C9 H9B 109.4 . . ?
O5 C9 C10 111.0(12) . . ?
H9A C9 H9B 108.0 . . ?
C10 C9 H9A 109.4 . . ?
C10 C9 H9B 109.4 . . ?
O1 C10 C9 108.9(12) . . ?
O1 C10 H10A 109.9 . . ?
O1 C10 H10B 109.9 . . ?
C9 C10 H10A 109.9 . . ?
C9 C10 H10B 109.9 . . ?
H10A C10 H10B 108.3 . . ?
C12 C11 I1 122.7(10) . . ?
C12 C11 C16 117.4(13) . . ?
C16 C11 I1 119.9(11) . . ?
F3 C12 C11 117.9(13) . . ?
F3 C12 C13 119.4(12) . . ?
C11 C12 C13 122.7(12) . . ?
C12 C13 I3 121.3(10) . . ?
C14 C13 I3 120.4(10) . . ?
C14 C13 C12 118.3(11) . . ?
F2 C14 C13 119.2(12) . . ?
F2 C14 C15 119.5(13) . . ?
C13 C14 C15 121.3(12) . . ?
C14 C15 I2 120.5(10) . . ?
C16 C15 I2 121.7(9) . . ?
C16 C15 C14 117.8(12) . . ?
F1 C16 C11 118.7(12) . . ?
F1 C16 C15 118.7(12) . . ?
C11 C16 C15 122.6(12) . . ?
C18 C17 I4 122.0(9) . . ?
C18 C17 C22 117.0(12) . . ?
C22 C17 I4 120.8(10) . . ?
F6 C18 C19 115.0(12) . . ?
C17 C18 F6 119.9(12) . . ?
C17 C18 C19 125.1(12) . . ?
C18 C19 I6 123.7(10) . . ?
C18 C19 C20 114.6(13) . . ?
C20 C19 I6 121.6(10) . . ?
F5 C20 C19 116.3(13) . . ?
C21 C20 F5 120.2(12) . . ?
C21 C20 C19 123.6(12) . . ?
C20 C21 I5 121.8(10) . . ?
C20 C21 C22 118.1(12) . . ?
C22 C21 I5 120.0(11) . . ?
F4 C22 C17 118.5(13) . . ?
F4 C22 C21 119.7(12) . . ?
C21 C22 C17 121.6(13) . . ?

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
O1 C1 C2 O2 -85(2) . . . . ?
O2 C3 C4 O3 51(3) . . . . ?
O3 C5 C6 O4 69(2) . . . . ?
O4 C7 C8 O5 -73.5(19) . . . . ?
O5 C9 C10 O1 -177.6(14) . . . . ?
C1 O1 C10 C9 -179.0(15) . . . . ?
C2 O2 C3 C4 -174(2) . . . . ?
C3 O2 C2 C1 169.2(16) . . . . ?
C4 O3 C5 C6 -167.8(17) . . . . ?
C5 O3 C4 C3 97(3) . . . . ?
C6 O4 C7 C8 -178.7(16) . . . . ?
C7 O4 C6 C5 -167.7(16) . . . . ?
C8 O5 C9 C10 -112.5(17) . . . . ?
C9 O5 C8 C7 111.0(16) . . . . ?
C10 O1 C1 C2 75(2) . . . . ?
I1 C11 C12 F3 2.2(18) . . . . ?
I1 C11 C12 C13 -179.8(10) . . . . ?
I1 C11 C16 F1 -0.5(17) . . . . ?
I1 C11 C16 C15 -179.8(10) . . . . ?
I2 C15 C16 F1 -1.9(17) . . . . ?
I2 C15 C16 C11 177.4(10) . . . . ?
I3 C13 C14 F2 0.0(18) . . . . ?
I3 C13 C14 C15 -178.8(10) . . . . ?
F2 C14 C15 I2 3.7(18) . . . . ?
F2 C14 C15 C16 -177.5(12) . . . . ?
F3 C12 C13 I3 -3.5(18) . . . . ?
F3 C12 C13 C14 178.7(13) . . . . ?
C11 C12 C13 I3 178.6(10) . . . . ?
C11 C12 C13 C14 1(2) . . . . ?
C12 C11 C16 F1 -179.6(12) . . . . ?
C12 C11 C16 C15 1(2) . . . . ?
C12 C13 C14 F2 177.8(12) . . . . ?
C12 C13 C14 C15 -1(2) . . . . ?
C13 C14 C15 I2 -177.5(10) . . . . ?
C13 C14 C15 C16 1(2) . . . . ?
C14 C15 C16 F1 179.3(12) . . . . ?
C14 C15 C16 C11 -1(2) . . . . ?
C16 C11 C12 F3 -178.8(12) . . . . ?
C16 C11 C12 C13 -1(2) . . . . ?
I4 C17 C18 F6 -3.6(18) . . . . ?
I4 C17 C18 C19 174.9(10) . . . . ?
I4 C17 C22 F4 8.1(17) . . . . ?
I4 C17 C22 C21 -176.5(10) . . . . ?
I5 C21 C22 F4 -4.5(18) . . . . ?
I5 C21 C22 C17 -179.9(10) . . . . ?
I6 C19 C20 F5 3.6(17) . . . . ?
I6 C19 C20 C21 -177.2(11) . . . . ?
F5 C20 C21 I5 0.8(19) . . . . ?
F5 C20 C21 C22 178.4(12) . . . . ?
F6 C18 C19 I6 -4.5(17) . . . . ?
F6 C18 C19 C20 179.0(11) . . . . ?
C17 C18 C19 I6 177.0(11) . . . . ?
C17 C18 C19 C20 0(2) . . . . ?
C18 C17 C22 F4 -178.0(12) . . . . ?
C18 C17 C22 C21 -3(2) . . . . ?
C18 C19 C20 F5 -179.9(12) . . . . ?
C18 C19 C20 C21 -1(2) . . . . ?
C19 C20 C21 I5 -178.4(10) . . . . ?
C19 C20 C21 C22 -1(2) . . . . ?
C20 C21 C22 F4 177.8(12) . . . . ?
C20 C21 C22 C17 2(2) . . . . ?
C22 C17 C18 F6 -177.4(12) . . . . ?
C22 C17 C18 C19 1(2) . . . . ?

_shelx_SHELXL_version_number     2014/7

_olex2_date_sample_data_collection 2016-07-02
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.514
_oxdiff_exptl_absorpt_empirical_full_min 0.668

# start Validation Reply Form
_vrf_PLAT431_C5-I135             
;
PROBLEM: Short Inter HL..A Contact I4 ..O5 . 2.88 Ang.
RESPONSE: The Checkcif software has a bug and cannot identify the halogen bond.
;
# end Validation Reply Form
####################################################################### 
# 
# 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_C5-I13-W
_database_code_depnum_ccdc_archive 'CCDC 2281938'
loop_
_audit_author_name
_audit_author_address
'Weizhou Wang'
;Luoyang Normal University
China
;
_audit_update_record             
;
2023-07-17 deposited with the CCDC.	2024-09-11 downloaded from the CCDC.
;
_audit_creation_date             2016-09-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.08.25 svn.r3337 for OlexSys, GUI svn.r5221)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 F4 I2, 2(H2 O), C10 H20 O5'
_chemical_formula_sum            'C16 H24 F4 I2 O7'
_chemical_formula_weight         658.15
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c h n o'
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.4810(5)
_cell_length_b                   22.1452(19)
_cell_length_c                   14.6860(11)
_cell_angle_alpha                90
_cell_angle_beta                 103.285(7)
_cell_angle_gamma                90
_cell_volume                     2367.9(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3637
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.0270
_cell_measurement_theta_min      3.8870
_shelx_estimated_absorpt_T_max   0.506
_shelx_estimated_absorpt_T_min   0.374
_exptl_absorpt_coefficient_mu    2.718
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.39892
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41r (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.846
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1272
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.29
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0468
_diffrn_reflns_av_unetI/netI     0.0603
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12945
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.500
_diffrn_reflns_theta_min         3.349
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0584
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -20.00  25.00   1.00    2.00    --  -13.48 -99.00-180.00   45
  2  ω    -20.00  25.00   1.00    2.00    --  -13.48 -99.00  30.00   45
  3  ω    -35.00  53.00   1.00    2.00    --  -13.48  77.00  90.00   88
  4  ω     -8.00  48.00   1.00    2.00    --  -13.48  19.00  60.00   56
  5  ω    -71.00 -29.00   1.00    2.00    --  -13.48 -77.00 -60.00   42
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0702349000
_diffrn_orient_matrix_UB_12      -0.0202316000
_diffrn_orient_matrix_UB_13      0.0055833000
_diffrn_orient_matrix_UB_21      -0.0662247000
_diffrn_orient_matrix_UB_22      0.0232033000
_diffrn_orient_matrix_UB_23      -0.0132371000
_diffrn_orient_matrix_UB_31      -0.0131555000
_diffrn_orient_matrix_UB_32      -0.0088361000
_diffrn_orient_matrix_UB_33      -0.0474966000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3201
_reflns_number_total             4376
_reflns_odcompleteness_completeness 99.68
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.13
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.953
_refine_diff_density_min         -0.673
_refine_diff_density_rms         0.111
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         4376
_refine_ls_number_restraints     165
_refine_ls_R_factor_all          0.0865
_refine_ls_R_factor_gt           0.0594
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0410P)²+7.9130P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1128
_refine_ls_wR_factor_ref         0.1279
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 C7-C8 = C9-C10 = C11-C12 = C13-C14 = C15-C16
 1.52 with sigma of 0.01
 O3-C8 = O3-C9 = O4-C10 = O4-C11 = O5-C12 = O5-C13
 1.45 with sigma of 0.02
 O6-C14 = O6-C15 = O7-C16 = O7-C7
 1.45 with sigma of 0.02
 C8-C9 \\sim C10-C11 \\sim C12-C13 \\sim C14-C15 \\sim C16-C7
 with sigma of 0.02
 C15-O7 \\sim C7-O3 \\sim C9-O4 \\sim C11-O5 \\sim C13-O6
 with sigma of 0.02
 O3-C10 \\sim O4-C12 \\sim O5-C14 \\sim O6-C16 \\sim O7-C8
 with sigma of 0.02
3. Rigid bond restraints
 O3, C9, C10, O4, C11, C12, O5, C13, C14, O6, C15, C16, O7, C7, C8
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
O3 \\sim C9 \\sim C10 \\sim O4 \\sim C11 \\sim C12 \\sim O5 \\sim C13 \\sim C14
\\sim O6 \\sim C15 \\sim C16 \\sim O7 \\sim C7 \\sim C8: within 2A with sigma
of 0.04 and sigma for terminal atoms of 0.08
5.a Riding coordinates:
 O1(H1A,H1B), O2(H2A,H2B)
5.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B),
 C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
F1 F 0.8898(7) 0.8880(2) 0.5870(4) 0.0731(14) Uani 1 1 d . . . . .
F2 F 0.8446(7) 0.9214(3) 0.4081(4) 0.0830(16) Uani 1 1 d . . . . .
F3 F 0.7223(7) 1.0333(2) 0.3529(3) 0.0762(15) Uani 1 1 d . . . . .
F4 F 0.6697(7) 1.0769(2) 0.6586(3) 0.0687(13) Uani 1 1 d . . . . .
I1 I 0.79713(8) 0.95346(3) 0.76481(4) 0.0610(2) Uani 1 1 d . . . . .
I2 I 0.60542(7) 1.14592(3) 0.46494(4) 0.0609(2) Uani 1 1 d . . . . .
O1 O 0.4959(10) 0.7295(3) 0.5750(5) 0.089(2) Uani 1 1 d . . . . .
H1A H 0.4201 0.7159 0.5271 0.134 Uiso 1 1 d R . . . .
H1B H 0.5711 0.7002 0.5870 0.134 Uiso 1 1 d R . . . .
O2 O 0.8012(10) 0.9100(3) 0.9474(4) 0.092(2) Uani 1 1 d . . . . .
H2A H 0.7195 0.9135 0.9788 0.138 Uiso 1 1 d R . . . .
H2B H 0.8408 0.8747 0.9640 0.138 Uiso 1 1 d R . . . .
O3 O 0.3427(16) 0.6464(5) 0.4203(7) 0.173(4) Uani 1 1 d D U . . .
O4 O 0.5564(13) 0.5789(5) 0.5685(7) 0.148(3) Uani 1 1 d D U . . .
O5 O 0.8242(14) 0.6607(5) 0.6549(7) 0.156(4) Uani 1 1 d D U . . .
O6 O 0.9129(19) 0.7160(7) 0.5020(10) 0.244(7) Uani 1 1 d D U . . .
O7 O 0.6159(18) 0.7113(6) 0.3564(10) 0.213(5) Uani 1 1 d D U . . .
C1 C 0.8216(10) 0.9431(4) 0.5614(6) 0.054(2) Uani 1 1 d . . . . .
C2 C 0.7994(11) 0.9605(4) 0.4699(6) 0.054(2) Uani 1 1 d . . . . .
C3 C 0.7380(10) 1.0171(4) 0.4429(6) 0.052(2) Uani 1 1 d . . . . .
C4 C 0.6934(10) 1.0580(4) 0.5053(5) 0.0492(19) Uani 1 1 d . . . . .
C5 C 0.7142(10) 1.0385(4) 0.5959(6) 0.0486(19) Uani 1 1 d . . . . .
C6 C 0.7770(10) 0.9822(4) 0.6271(5) 0.0482(19) Uani 1 1 d . . . . .
C7 C 0.426(2) 0.7159(7) 0.3211(11) 0.193(6) Uani 1 1 d D U . . .
H7A H 0.4006 0.7292 0.2565 0.232 Uiso 1 1 calc R . . . .
H7B H 0.3751 0.7452 0.3571 0.232 Uiso 1 1 calc R . . . .
C8 C 0.341(2) 0.6544(7) 0.3276(9) 0.186(6) Uani 1 1 d D U . . .
H8A H 0.2167 0.6531 0.2898 0.224 Uiso 1 1 calc R . . . .
H8B H 0.4126 0.6231 0.3062 0.224 Uiso 1 1 calc R . . . .
C9 C 0.313(2) 0.5859(7) 0.4418(9) 0.171(5) Uani 1 1 d D U . . .
H9A H 0.3851 0.5594 0.4116 0.205 Uiso 1 1 calc R . . . .
H9B H 0.1845 0.5757 0.4193 0.205 Uiso 1 1 calc R . . . .
C10 C 0.3698(18) 0.5776(7) 0.5476(9) 0.168(5) Uani 1 1 d D U . . .
H10A H 0.3214 0.6100 0.5794 0.202 Uiso 1 1 calc R . . . .
H10B H 0.3254 0.5394 0.5659 0.202 Uiso 1 1 calc R . . . .
C11 C 0.6283(18) 0.5838(7) 0.6668(9) 0.170(5) Uani 1 1 d D U . . .
H11A H 0.6170 0.5455 0.6970 0.204 Uiso 1 1 calc R . . . .
H11B H 0.5609 0.6141 0.6930 0.204 Uiso 1 1 calc R . . . .
C12 C 0.8285(18) 0.6016(7) 0.6826(8) 0.164(5) Uani 1 1 d D U . . .
H12A H 0.8902 0.5975 0.7480 0.197 Uiso 1 1 calc R . . . .
H12B H 0.8913 0.5767 0.6454 0.197 Uiso 1 1 calc R . . . .
C13 C 1.0057(18) 0.6772(7) 0.6485(11) 0.185(6) Uani 1 1 d D U . . .
H13A H 1.0626 0.6441 0.6225 0.222 Uiso 1 1 calc R . . . .
H13B H 1.0802 0.6863 0.7102 0.222 Uiso 1 1 calc R . . . .
C14 C 0.993(2) 0.7320(8) 0.5863(11) 0.206(7) Uani 1 1 d D U . . .
H14A H 0.9231 0.7635 0.6080 0.247 Uiso 1 1 calc R . . . .
H14B H 1.1151 0.7474 0.5877 0.247 Uiso 1 1 calc R . . . .
C15 C 0.898(2) 0.7517(9) 0.4284(12) 0.217(7) Uani 1 1 d D U . . .
H15A H 0.9747 0.7354 0.3891 0.260 Uiso 1 1 calc R . . . .
H15B H 0.9473 0.7910 0.4500 0.260 Uiso 1 1 calc R . . . .
C16 C 0.710(2) 0.7598(9) 0.3703(15) 0.234(8) Uani 1 1 d D U . . .
H16A H 0.6455 0.7889 0.4007 0.281 Uiso 1 1 calc R . . . .
H16B H 0.7173 0.7766 0.3103 0.281 Uiso 1 1 calc R . . . .


_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
F1 C1 1.342(9) . ?
F2 C2 1.352(9) . ?
F3 C3 1.348(9) . ?
F4 C5 1.350(8) . ?
I1 C6 2.092(7) . ?
I2 C4 2.096(8) . ?
O1 H1A 0.8502 . ?
O1 H1B 0.8501 . ?
O2 H2A 0.8497 . ?
O2 H2B 0.8510 . ?
O3 C8 1.369(12) . ?
O3 C9 1.407(13) . ?
O4 C10 1.359(12) . ?
O4 C11 1.424(12) . ?
O5 C12 1.370(12) . ?
O5 C13 1.430(12) . ?
O6 C14 1.296(14) . ?
O6 C15 1.322(13) . ?
O7 C7 1.396(14) . ?
O7 C16 1.274(14) . ?
C1 C2 1.371(11) . ?
C1 C6 1.393(11) . ?
C2 C3 1.361(11) . ?
C3 C4 1.383(11) . ?
C4 C5 1.375(11) . ?
C5 C6 1.374(10) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.516(9) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.525(9) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.514(9) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.508(9) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.484(9) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?

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
H1A O1 H1B 100.7 . . ?
H2A O2 H2B 100.1 . . ?
C8 O3 C9 112.3(9) . . ?
C10 O4 C11 111.1(8) . . ?
C12 O5 C13 107.8(9) . . ?
C14 O6 C15 123.4(14) . . ?
C16 O7 C7 118.2(13) . . ?
F1 C1 C2 118.8(8) . . ?
F1 C1 C6 120.5(8) . . ?
C2 C1 C6 120.7(8) . . ?
F2 C2 C1 119.0(8) . . ?
F2 C2 C3 120.9(8) . . ?
C3 C2 C1 120.1(8) . . ?
F3 C3 C2 118.5(8) . . ?
F3 C3 C4 119.7(8) . . ?
C2 C3 C4 121.8(8) . . ?
C3 C4 I2 122.0(6) . . ?
C5 C4 I2 121.6(6) . . ?
C5 C4 C3 116.4(7) . . ?
F4 C5 C4 118.2(7) . . ?
F4 C5 C6 117.6(7) . . ?
C6 C5 C4 124.2(7) . . ?
C1 C6 I1 120.4(6) . . ?
C5 C6 I1 122.8(6) . . ?
C5 C6 C1 116.8(7) . . ?
O7 C7 H7A 110.0 . . ?
O7 C7 H7B 110.0 . . ?
O7 C7 C8 108.4(12) . . ?
H7A C7 H7B 108.4 . . ?
C8 C7 H7A 110.0 . . ?
C8 C7 H7B 110.0 . . ?
O3 C8 C7 105.7(11) . . ?
O3 C8 H8A 110.6 . . ?
O3 C8 H8B 110.6 . . ?
C7 C8 H8A 110.6 . . ?
C7 C8 H8B 110.6 . . ?
H8A C8 H8B 108.7 . . ?
O3 C9 H9A 109.9 . . ?
O3 C9 H9B 109.9 . . ?
O3 C9 C10 108.8(11) . . ?
H9A C9 H9B 108.3 . . ?
C10 C9 H9A 109.9 . . ?
C10 C9 H9B 109.9 . . ?
O4 C10 C9 105.0(10) . . ?
O4 C10 H10A 110.8 . . ?
O4 C10 H10B 110.8 . . ?
C9 C10 H10A 110.8 . . ?
C9 C10 H10B 110.8 . . ?
H10A C10 H10B 108.8 . . ?
O4 C11 H11A 110.2 . . ?
O4 C11 H11B 110.2 . . ?
O4 C11 C12 107.7(10) . . ?
H11A C11 H11B 108.5 . . ?
C12 C11 H11A 110.2 . . ?
C12 C11 H11B 110.2 . . ?
O5 C12 C11 104.4(11) . . ?
O5 C12 H12A 110.9 . . ?
O5 C12 H12B 110.9 . . ?
C11 C12 H12A 110.9 . . ?
C11 C12 H12B 110.9 . . ?
H12A C12 H12B 108.9 . . ?
O5 C13 H13A 110.0 . . ?
O5 C13 H13B 110.0 . . ?
O5 C13 C14 108.5(10) . . ?
H13A C13 H13B 108.4 . . ?
C14 C13 H13A 110.0 . . ?
C14 C13 H13B 110.0 . . ?
O6 C14 C13 108.0(14) . . ?
O6 C14 H14A 110.1 . . ?
O6 C14 H14B 110.1 . . ?
C13 C14 H14A 110.1 . . ?
C13 C14 H14B 110.1 . . ?
H14A C14 H14B 108.4 . . ?
O6 C15 H15A 108.4 . . ?
O6 C15 H15B 108.4 . . ?
O6 C15 C16 115.5(13) . . ?
H15A C15 H15B 107.5 . . ?
C16 C15 H15A 108.4 . . ?
C16 C15 H15B 108.4 . . ?
O7 C16 C15 113.9(15) . . ?
O7 C16 H16A 108.8 . . ?
O7 C16 H16B 108.8 . . ?
C15 C16 H16A 108.8 . . ?
C15 C16 H16B 108.8 . . ?
H16A C16 H16B 107.7 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1A O3 0.85 2.18 2.943(12) 149.5 .
O1 H1B O5 0.85 2.12 2.899(12) 153.0 .
O2 H2A O4 0.85 2.00 2.841(11) 172.0 4_576
O2 H2B O6 0.85 2.12 2.970(17) 174.5 4_576

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
F1 C1 C2 F2 0.9(11) . . . . ?
F1 C1 C2 C3 -177.2(7) . . . . ?
F1 C1 C6 I1 -4.6(10) . . . . ?
F1 C1 C6 C5 177.7(7) . . . . ?
F2 C2 C3 F3 0.3(12) . . . . ?
F2 C2 C3 C4 -179.1(7) . . . . ?
F3 C3 C4 I2 -1.0(10) . . . . ?
F3 C3 C4 C5 -179.5(7) . . . . ?
F4 C5 C6 I1 2.1(10) . . . . ?
F4 C5 C6 C1 179.7(6) . . . . ?
I2 C4 C5 F4 2.4(9) . . . . ?
I2 C4 C5 C6 -177.8(6) . . . . ?
O3 C9 C10 O4 -73.6(15) . . . . ?
O4 C11 C12 O5 72.2(14) . . . . ?
O5 C13 C14 O6 -67.6(19) . . . . ?
O6 C15 C16 O7 -42(3) . . . . ?
O7 C7 C8 O3 74.9(18) . . . . ?
C1 C2 C3 F3 178.3(7) . . . . ?
C1 C2 C3 C4 -1.1(12) . . . . ?
C2 C1 C6 I1 176.5(6) . . . . ?
C2 C1 C6 C5 -1.2(11) . . . . ?
C2 C3 C4 I2 178.4(6) . . . . ?
C2 C3 C4 C5 -0.1(11) . . . . ?
C3 C4 C5 F4 -179.1(6) . . . . ?
C3 C4 C5 C6 0.7(11) . . . . ?
C4 C5 C6 I1 -177.7(6) . . . . ?
C4 C5 C6 C1 0.0(11) . . . . ?
C6 C1 C2 F2 179.8(7) . . . . ?
C6 C1 C2 C3 1.7(12) . . . . ?
C7 O7 C16 C15 165.9(16) . . . . ?
C8 O3 C9 C10 164.1(12) . . . . ?
C9 O3 C8 C7 -164.4(12) . . . . ?
C10 O4 C11 C12 -165.1(12) . . . . ?
C11 O4 C10 C9 168.3(11) . . . . ?
C12 O5 C13 C14 159.5(12) . . . . ?
C13 O5 C12 C11 -167.7(11) . . . . ?
C14 O6 C15 C16 -127(2) . . . . ?
C15 O6 C14 C13 -172.3(17) . . . . ?
C16 O7 C7 C8 -169.5(18) . . . . ?

_shelx_SHELXL_version_number     2014/7

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.180
_oxdiff_exptl_absorpt_empirical_full_min 0.572
####################################################################### 
# 
# 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_C6-I13
_database_code_depnum_ccdc_archive 'CCDC 2281932'
loop_
_audit_author_name
_audit_author_address
'Weizhou Wang'
;Luoyang Normal University
China
;
_audit_update_record             
;
2023-07-17 deposited with the CCDC.	2024-09-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H12 F4 I2 O3'
_chemical_formula_weight         534.02

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'
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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pbca

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

_cell_length_a                   7.8540(6)
_cell_length_b                   15.3678(14)
_cell_length_c                   27.2763(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3292.2(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2500
_cell_measurement_theta_min      3.47
_cell_measurement_theta_max      25.50

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.155
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2000
_exptl_absorpt_coefficient_mu    3.866
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3001
_exptl_absorpt_correction_T_max  0.4572
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            9490
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_av_sigmaI/netI    0.0414
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         3.47
_diffrn_reflns_theta_max         25.50
_reflns_number_total             3056
_reflns_number_gt                2437
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0394P)²+3.7504P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.00138(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3056
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0665
_refine_ls_R_factor_gt           0.0490
_refine_ls_wR_factor_ref         0.1059
_refine_ls_wR_factor_gt          0.0987
_refine_ls_goodness_of_fit_ref   1.133
_refine_ls_restrained_S_all      1.133
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.8985(6) 0.7239(3) 0.12053(14) 0.0772(13) Uani 1 1 d . . .
F2 F 0.9425(9) 0.8267(3) 0.2001(2) 0.124(2) Uani 1 1 d . . .
F3 F 0.9168(8) 0.7606(3) 0.28976(16) 0.1045(17) Uani 1 1 d . . .
F4 F 0.8048(6) 0.4857(3) 0.22349(15) 0.0757(14) Uani 1 1 d . . .
I1 I 0.82778(6) 0.52184(4) 0.109008(16) 0.0598(2) Uani 1 1 d . . .
I2 I 0.83965(6) 0.56868(3) 0.329159(16) 0.0546(2) Uani 1 1 d . . .
O1 O 0.8449(5) 0.4792(3) 0.42440(16) 0.0515(12) Uani 1 1 d . . .
O2 O 0.6208(5) 0.3242(3) 0.43937(15) 0.0482(11) Uani 1 1 d . . .
O3 O 0.3136(5) 0.3878(3) 0.47783(15) 0.0451(11) Uani 1 1 d . . .
C1 C 0.9052(12) 0.7421(5) 0.2054(3) 0.072(2) Uani 1 1 d . . .
C2 C 0.8915(10) 0.7067(5) 0.2514(3) 0.061(2) Uani 1 1 d . . .
C3 C 0.8568(7) 0.6206(4) 0.2587(2) 0.0420(15) Uani 1 1 d . . .
C4 C 0.8365(7) 0.5696(4) 0.2174(2) 0.0425(16) Uani 1 1 d . . .
C5 C 0.8505(7) 0.6022(4) 0.1706(2) 0.0413(15) Uani 1 1 d . . .
C6 C 0.8839(8) 0.6892(4) 0.1653(2) 0.0483(17) Uani 1 1 d . . .
C7 C 0.7702(9) 0.4963(4) 0.4711(2) 0.0445(15) Uani 1 1 d . . .
H7A H 0.8397 0.4718 0.4970 0.053 Uiso 1 1 calc R . .
H7B H 0.6573 0.4710 0.4730 0.053 Uiso 1 1 calc R . .
C8 C 0.8805(8) 0.3900(4) 0.4154(3) 0.0493(17) Uani 1 1 d . . .
H8A H 0.9249 0.3643 0.4452 0.059 Uiso 1 1 calc R . .
H8B H 0.9690 0.3863 0.3907 0.059 Uiso 1 1 calc R . .
C9 C 0.7312(9) 0.3375(5) 0.3986(2) 0.0532(17) Uani 1 1 d . . .
H9A H 0.6713 0.3679 0.3727 0.064 Uiso 1 1 calc R . .
H9B H 0.7695 0.2819 0.3859 0.064 Uiso 1 1 calc R . .
C10 C 0.4627(8) 0.2883(4) 0.4273(2) 0.0469(16) Uani 1 1 d . . .
H10A H 0.4751 0.2271 0.4193 0.056 Uiso 1 1 calc R . .
H10B H 0.4143 0.3181 0.3992 0.056 Uiso 1 1 calc R . .
C11 C 0.3495(8) 0.2990(4) 0.4712(2) 0.0502(17) Uani 1 1 d . . .
H11A H 0.2445 0.2669 0.4663 0.060 Uiso 1 1 calc R . .
H11B H 0.4057 0.2760 0.5001 0.060 Uiso 1 1 calc R . .
C12 C 0.2391(9) 0.4067(4) 0.5240(2) 0.0454(15) Uani 1 1 d . . .
H12A H 0.3079 0.3824 0.5502 0.054 Uiso 1 1 calc R . .
H12B H 0.1260 0.3816 0.5260 0.054 Uiso 1 1 calc R . .


_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
F1 C6 1.338(7) . ?
F2 C1 1.341(8) . ?
F3 C2 1.348(8) . ?
F4 C4 1.324(7) . ?
I1 C5 2.093(6) . ?
I2 C3 2.086(6) . ?
O1 C8 1.421(7) . ?
O1 C7 1.426(7) . ?
O2 C10 1.398(7) . ?
O2 C9 1.424(7) . ?
O3 C11 1.406(7) . ?
O3 C12 1.420(7) . ?
C1 C6 1.371(10) . ?
C1 C2 1.373(10) . ?
C2 C3 1.366(10) . ?
C3 C4 1.381(9) . ?
C4 C5 1.377(8) . ?
C5 C6 1.370(9) . ?
C7 C12 1.499(8) 5_666 ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.495(9) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.499(8) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C7 1.499(8) 5_666 ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?

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
C8 O1 C7 114.4(5) . . ?
C10 O2 C9 114.5(5) . . ?
C11 O3 C12 113.3(5) . . ?
F2 C1 C6 121.0(7) . . ?
F2 C1 C2 119.9(7) . . ?
C6 C1 C2 119.0(7) . . ?
F3 C2 C3 120.8(6) . . ?
F3 C2 C1 117.1(7) . . ?
C3 C2 C1 122.1(7) . . ?
C2 C3 C4 117.1(6) . . ?
C2 C3 I2 121.1(5) . . ?
C4 C3 I2 121.8(5) . . ?
F4 C4 C5 119.1(6) . . ?
F4 C4 C3 118.2(6) . . ?
C5 C4 C3 122.7(6) . . ?
C6 C5 C4 117.9(6) . . ?
C6 C5 I1 120.6(5) . . ?
C4 C5 I1 121.5(5) . . ?
F1 C6 C1 118.7(6) . . ?
F1 C6 C5 120.1(6) . . ?
C1 C6 C5 121.2(6) . . ?
O1 C7 C12 106.4(5) . 5_666 ?
O1 C7 H7A 110.5 . . ?
C12 C7 H7A 110.5 5_666 . ?
O1 C7 H7B 110.5 . . ?
C12 C7 H7B 110.5 5_666 . ?
H7A C7 H7B 108.6 . . ?
O1 C8 C9 114.9(5) . . ?
O1 C8 H8A 108.6 . . ?
C9 C8 H8A 108.6 . . ?
O1 C8 H8B 108.6 . . ?
C9 C8 H8B 108.6 . . ?
H8A C8 H8B 107.5 . . ?
O2 C9 C8 108.5(5) . . ?
O2 C9 H9A 110.0 . . ?
C8 C9 H9A 110.0 . . ?
O2 C9 H9B 110.0 . . ?
C8 C9 H9B 110.0 . . ?
H9A C9 H9B 108.4 . . ?
O2 C10 C11 107.2(5) . . ?
O2 C10 H10A 110.3 . . ?
C11 C10 H10A 110.3 . . ?
O2 C10 H10B 110.3 . . ?
C11 C10 H10B 110.3 . . ?
H10A C10 H10B 108.5 . . ?
O3 C11 C10 109.2(5) . . ?
O3 C11 H11A 109.8 . . ?
C10 C11 H11A 109.8 . . ?
O3 C11 H11B 109.8 . . ?
C10 C11 H11B 109.8 . . ?
H11A C11 H11B 108.3 . . ?
O3 C12 C7 107.6(5) . 5_666 ?
O3 C12 H12A 110.2 . . ?
C7 C12 H12A 110.2 5_666 . ?
O3 C12 H12B 110.2 . . ?
C7 C12 H12B 110.2 5_666 . ?
H12A C12 H12B 108.5 . . ?

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
F2 C1 C2 F3 0.1(12) . . . . ?
C6 C1 C2 F3 178.7(8) . . . . ?
F2 C1 C2 C3 -178.8(8) . . . . ?
C6 C1 C2 C3 -0.2(13) . . . . ?
F3 C2 C3 C4 -178.6(6) . . . . ?
C1 C2 C3 C4 0.3(11) . . . . ?
F3 C2 C3 I2 0.4(10) . . . . ?
C1 C2 C3 I2 179.3(6) . . . . ?
C2 C3 C4 F4 179.2(6) . . . . ?
I2 C3 C4 F4 0.2(8) . . . . ?
C2 C3 C4 C5 0.2(9) . . . . ?
I2 C3 C4 C5 -178.8(5) . . . . ?
F4 C4 C5 C6 -179.8(6) . . . . ?
C3 C4 C5 C6 -0.8(9) . . . . ?
F4 C4 C5 I1 -1.3(8) . . . . ?
C3 C4 C5 I1 177.7(4) . . . . ?
F2 C1 C6 F1 -1.0(12) . . . . ?
C2 C1 C6 F1 -179.6(7) . . . . ?
F2 C1 C6 C5 178.1(7) . . . . ?
C2 C1 C6 C5 -0.4(12) . . . . ?
C4 C5 C6 F1 -180.0(6) . . . . ?
I1 C5 C6 F1 1.5(8) . . . . ?
C4 C5 C6 C1 0.9(10) . . . . ?
I1 C5 C6 C1 -177.6(6) . . . . ?
C8 O1 C7 C12 173.8(5) . . . 5_666 ?
C7 O1 C8 C9 81.4(7) . . . . ?
C10 O2 C9 C8 170.1(5) . . . . ?
O1 C8 C9 O2 -73.1(7) . . . . ?
C9 O2 C10 C11 -166.5(5) . . . . ?
C12 O3 C11 C10 -167.0(5) . . . . ?
O2 C10 C11 O3 68.3(6) . . . . ?
C11 O3 C12 C7 172.4(5) . . . 5_666 ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.880
_refine_diff_density_min         -0.656
_refine_diff_density_rms         0.103

# start Validation Reply Form
_vrf_PLAT431_C6-I13              
;
PROBLEM: Short Inter HL..A Contact I2 ..O1 . 2.94 Ang.
RESPONSE: The Checkcif software has a bug and cannot identify the halogen bond.
;
# end Validation Reply Form

####################################################################### 
# 
# 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_C6-I135
_database_code_depnum_ccdc_archive 'CCDC 2281937'
loop_
_audit_author_name
_audit_author_address
'Weizhou Wang'
;Luoyang Normal University
China
;
_audit_update_record             
;
2023-07-17 deposited with the CCDC.	2024-09-11 downloaded from the CCDC.
;
_audit_creation_date             2016-09-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.08.25 svn.r3337 for OlexSys, GUI svn.r5221)
;
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         '2(C6 F3 I3), C12 H24 O6'
_chemical_formula_sum            'C24 H24 F6 I6 O6'
_chemical_formula_weight         1283.87
_chemical_oxdiff_formula         'C H O I F'
_chemical_oxdiff_usercomment     18
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
I -0.41187 1.83264 20.14720 18.99490 7.51380 2.27350 4.34700 0.38140 27.76600
66.87760 4.07119989395
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.01794 0.01033 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   8.5263(6)
_cell_length_b                   25.6556(16)
_cell_length_c                   8.8944(5)
_cell_angle_alpha                90
_cell_angle_beta                 115.244(8)
_cell_angle_gamma                90
_cell_volume                     1759.8(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2559
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.1300
_cell_measurement_theta_min      3.5460
_exptl_absorpt_coefficient_mu    5.361
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.17258
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.4227
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1171.7407
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.21
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0435
_diffrn_reflns_av_unetI/netI     0.0538
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8707
_diffrn_reflns_theta_full        26.0000
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         3.19
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.2542
_diffrn_measured_fraction_theta_full 0.9966
_diffrn_measured_fraction_theta_max 0.9966
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -23.00   60.00   1.0000    3.5100
omega____ theta____ kappa____ phi______ frames
    -       18.5767  -99.0000 -150.0000 83

#__ type_ start__ end____ width___ exp.time_
  2 omega   -9.00   17.00   1.0000    3.5100
omega____ theta____ kappa____ phi______ frames
    -       18.5767   77.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
  3 omega   54.00   88.00   1.0000    3.5100
omega____ theta____ kappa____ phi______ frames
    -       18.5767   77.0000   90.0000 34

#__ type_ start__ end____ width___ exp.time_
  4 omega   -2.00   35.00   1.0000    3.5100
omega____ theta____ kappa____ phi______ frames
    -       18.5767   57.0000   90.0000 37

#__ type_ start__ end____ width___ exp.time_
  5 omega    6.00   87.00   1.0000    3.5100
omega____ theta____ kappa____ phi______ frames
    -       18.5767   57.0000    0.0000 81
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0636758000
_diffrn_orient_matrix_UB_12      -0.0148180000
_diffrn_orient_matrix_UB_13      -0.0644716000
_diffrn_orient_matrix_UB_21      -0.0462885000
_diffrn_orient_matrix_UB_22      0.0231851000
_diffrn_orient_matrix_UB_23      -0.0357555000
_diffrn_orient_matrix_UB_31      0.0476072000
_diffrn_orient_matrix_UB_32      0.0026668000
_diffrn_orient_matrix_UB_33      -0.0483324000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -10
_reflns_limit_k_max              30
_reflns_limit_k_min              0
_reflns_limit_l_max              10
_reflns_limit_l_min              0
_reflns_number_gt                2510
_reflns_number_total             3266
_reflns_odcompleteness_completeness 99.49
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         2.3749
_refine_diff_density_min         -1.6558
_refine_diff_density_rms         0.2542
_refine_ls_d_res_high            0.8255
_refine_ls_d_res_low             6.3765
_refine_ls_goodness_of_fit_ref   1.0778
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    18
_refine_ls_number_parameters     189
_refine_ls_number_reflns         3266
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0815
_refine_ls_R_factor_gt           0.0629
_refine_ls_restrained_S_all      1.0778
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0578P)²+16.7365P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1510
_refine_ls_wR_factor_ref         0.1642
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7a,H7b), C8(H8a,H8b), C9(H9a,H9b), C10(H10a,H10b), C11(H11a,H11b),
 C12(H12a,H12b)
;
_atom_sites_solution_primary     dual
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_refinement_flags_posn
C1 C 0.6648(14) 0.1889(4) 0.5807(13) 0.042(2) Uani 1.000000 .
C2 C 0.8125(14) 0.1900(5) 0.7326(13) 0.047(3) Uani 1.000000 .
C3 C 0.8820(13) 0.2351(5) 0.8119(12) 0.048(3) Uani 1.000000 .
C4 C 0.8077(14) 0.2815(4) 0.7427(12) 0.042(2) Uani 1.000000 .
C5 C 0.6618(13) 0.2833(4) 0.5917(12) 0.039(2) Uani 1.000000 .
C6 C 0.5940(13) 0.2367(4) 0.5159(11) 0.039(2) Uani 1.000000 .
C7 C 0.1847(15) 0.4436(5) 0.2161(13) 0.050(3) Uani 1.000000 .
H7a H 0.1325(15) 0.4779(5) 0.1985(13) 0.060(3) Uiso 1.000000 R
H7b H 0.1507(15) 0.4251(5) 0.2927(13) 0.060(3) Uiso 1.000000 R
C8 C 0.4270(16) 0.4934(4) 0.2336(15) 0.055(3) Uani 1.000000 .
H8a H 0.3758(16) 0.5250(4) 0.2527(15) 0.066(3) Uiso 1.000000 R
H8b H 0.3949(16) 0.4904(4) 0.1154(15) 0.066(3) Uiso 1.000000 R
C9 C 0.6168(15) 0.4955(5) 0.3258(13) 0.052(3) Uani 1.000000 .
H9a H 0.6490(15) 0.5033(5) 0.4420(13) 0.062(3) Uiso 1.000000 R
H9b H 0.6674(15) 0.4622(5) 0.3189(13) 0.062(3) Uiso 1.000000 R
C10 C 0.8588(15) 0.5395(6) 0.3264(13) 0.059(3) Uani 1.000000 .
H10a H 0.9103(15) 0.5053(6) 0.3330(13) 0.071(4) Uiso 1.000000 R
H10b H 0.8988(15) 0.5532(6) 0.4383(13) 0.071(4) Uiso 1.000000 R
C11 C 0.9127(14) 0.5752(5) 0.2233(14) 0.056(3) Uani 1.000000 .
H11a H 0.8540(14) 0.6085(5) 0.2092(14) 0.067(4) Uiso 1.000000 R
H11b H 1.0367(14) 0.5813(5) 0.2783(14) 0.067(4) Uiso 1.000000 R
C12 C 0.8874(16) 0.5854(5) -0.0513(14) 0.056(3) Uani 1.000000 .
H12a H 1.0086(16) 0.5938(5) -0.0176(14) 0.067(4) Uiso 1.000000 R
H12b H 0.8240(16) 0.6176(5) -0.0615(14) 0.067(4) Uiso 1.000000 R
F1 F 0.8847(10) 0.1441(3) 0.7990(9) 0.069(2) Uani 1.000000 .
F2 F 0.8750(9) 0.3253(3) 0.8187(9) 0.0651(19) Uani 1.000000 .
F3 F 0.4553(8) 0.2372(3) 0.3672(8) 0.0577(18) Uani 1.000000 .
I1 I 0.54847(12) 0.12052(3) 0.46332(11) 0.0643(3) Uani 1.000000 .
I2 I 1.11020(11) 0.23418(5) 1.03297(10) 0.0737(4) Uani 1.000000 .
I3 I 0.55059(11) 0.35367(3) 0.47564(10) 0.0566(3) Uani 1.000000 .
O1 O 0.3656(10) 0.4492(3) 0.2900(9) 0.0501(18) Uani 1.000000 .
O2 O 0.6768(9) 0.5353(3) 0.2528(9) 0.0526(19) Uani 1.000000 .
O3 O 0.8688(10) 0.5520(3) 0.0688(9) 0.055(2) Uani 1.000000 .


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 1.400(15) . ?
C1 C6 1.381(14) . ?
C1 I1 2.066(10) . ?
C2 C3 1.354(17) . ?
C2 F1 1.343(13) . ?
C3 C4 1.364(16) . ?
C3 I2 2.095(10) . ?
C4 C5 1.389(14) . ?
C4 F2 1.311(12) . ?
C5 C6 1.373(14) . ?
C5 I3 2.095(10) . ?
C6 F3 1.346(11) . ?
C7 H7a 0.9700 . ?
C7 H7b 0.9700 . ?
C7 C12 1.520(15) 3_665 ?
C7 O1 1.402(13) . ?
C8 H8a 0.9700 . ?
C8 H8b 0.9700 . ?
C8 C9 1.470(16) . ?
C8 O1 1.427(12) . ?
C9 H9a 0.9700 . ?
C9 H9b 0.9700 . ?
C9 O2 1.418(13) . ?
C10 H10a 0.9700 . ?
C10 H10b 0.9700 . ?
C10 C11 1.501(16) . ?
C10 O2 1.408(13) . ?
C11 H11a 0.9700 . ?
C11 H11b 0.9700 . ?
C11 O3 1.395(13) . ?
C12 H12a 0.9700 . ?
C12 H12b 0.9700 . ?
C12 O3 1.430(13) . ?

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 C1 C2 116.0(10) . . ?
I1 C1 C2 123.1(8) . . ?
I1 C1 C6 120.9(8) . . ?
C3 C2 C1 122.3(11) . . ?
F1 C2 C1 117.5(11) . . ?
F1 C2 C3 120.3(10) . . ?
C4 C3 C2 119.6(10) . . ?
I2 C3 C2 120.3(9) . . ?
I2 C3 C4 120.0(9) . . ?
C5 C4 C3 121.2(10) . . ?
F2 C4 C3 119.8(10) . . ?
F2 C4 C5 119.0(10) . . ?
C6 C5 C4 117.5(10) . . ?
I3 C5 C4 122.4(8) . . ?
I3 C5 C6 120.1(7) . . ?
C5 C6 C1 123.4(9) . . ?
F3 C6 C1 117.5(9) . . ?
F3 C6 C5 119.0(9) . . ?
H7b C7 H7a 107.6 . . ?
C12 C7 H7a 108.6(7) 3_665 . ?
C12 C7 H7b 108.6(6) 3_665 . ?
O1 C7 H7a 108.6(6) . . ?
O1 C7 H7b 108.6(5) . . ?
O1 C7 C12 114.5(9) . 3_665 ?
H8b C8 H8a 108.384049450(15) . . ?
C9 C8 H8a 110.0(7) . . ?
C9 C8 H8b 110.0(7) . . ?
O1 C8 H8a 110.0(6) . . ?
O1 C8 H8b 110.0(6) . . ?
O1 C8 C9 108.3(9) . . ?
H9a C9 C8 110.3(7) . . ?
H9b C9 C8 110.3(7) . . ?
H9b C9 H9a 108.5 . . ?
O2 C9 C8 107.3(9) . . ?
O2 C9 H9a 110.3(6) . . ?
O2 C9 H9b 110.3(6) . . ?
H10b C10 H10a 108.3 . . ?
C11 C10 H10a 109.9(7) . . ?
C11 C10 H10b 109.9(6) . . ?
O2 C10 H10a 109.9(7) . . ?
O2 C10 H10b 109.9(6) . . ?
O2 C10 C11 109.0(9) . . ?
H11a C11 C10 110.0(7) . . ?
H11b C11 C10 110.0(6) . . ?
H11b C11 H11a 108.4 . . ?
O3 C11 C10 108.5(10) . . ?
O3 C11 H11a 110.0(6) . . ?
O3 C11 H11b 110.0(6) . . ?
H12a C12 C7 110.2(6) . 3_665 ?
H12b C12 C7 110.2(7) . 3_665 ?
H12b C12 H12a 108.5 . . ?
O3 C12 C7 107.4(9) . 3_665 ?
O3 C12 H12a 110.2(6) . . ?
O3 C12 H12b 110.2(6) . . ?
C8 O1 C7 114.3(8) . . ?
C10 O2 C9 112.6(8) . . ?
C12 O3 C11 114.2(9) . . ?


_olex2_submission_special_instructions 'No special instructions were received'
