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

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

data_Cocrystal_1_Mother_domain
_database_code_depnum_ccdc_archive 'CCDC 2256404'
loop_
_audit_author_name
_audit_author_address
'Subham Ranjan'
;Yokohama City University
Japan
;
_audit_update_record             
;
2023-04-14 deposited with the CCDC.	2023-10-16 downloaded from the CCDC.
;
_audit_creation_date             2023-04-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C3 F2 I, C6 H6 N'
_chemical_formula_sum            'C9 H6 F2 I N'
_chemical_formula_weight         293.05
_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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   5.03760(10)
_cell_length_b                   9.9157(3)
_cell_length_c                   10.6198(3)
_cell_angle_alpha                64.7690(10)
_cell_angle_beta                 82.1290(10)
_cell_angle_gamma                87.8810(10)
_cell_volume                     475.21(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7450
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.95
_cell_measurement_theta_min      2.27
_exptl_absorpt_coefficient_mu    3.350
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.4413
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;

_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.048
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             276
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_unetI/netI     0.0266
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8617
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.27
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean 7.391
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'graphite monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         0
_reflns_number_gt                1599
_reflns_number_total             1658
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'APEX3 v2019.11 (Bruker AXS Inc., 2019)'
_computing_data_collection       'Bruker Instrument Service (Bruker AXS Inc.)'
_computing_data_reduction        'SAINT (Bruker AXS Inc.)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2013)'
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       0.039(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         1658
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0167
_refine_ls_R_factor_gt           0.0157
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0180P)²+0.1703P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0401
_refine_ls_wR_factor_ref         0.0405
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C5(H5), C4(H4)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I -0.00734(3) 0.312633(17) 0.371511(16) 0.05014(10) Uani 1 1 d . . .
F2 F -0.3780(3) 0.5874(2) 0.22042(15) 0.0701(5) Uani 1 1 d . . .
F1 F -0.2399(4) 0.27456(19) 0.68470(16) 0.0705(5) Uani 1 1 d . . .
N1 N 0.3862(4) 0.1817(3) 0.2500(2) 0.0567(5) Uani 1 1 d . . .
C8 C -0.2987(4) 0.4264(3) 0.4487(2) 0.0423(5) Uani 1 1 d . . .
C9 C -0.4344(5) 0.5432(3) 0.3597(2) 0.0464(5) Uani 1 1 d . . .
C7 C -0.3687(5) 0.3856(3) 0.5910(2) 0.0457(5) Uani 1 1 d . . .
C3 C 0.8228(5) 0.0963(3) 0.1105(2) 0.0457(5) Uani 1 1 d . . .
C1 C 0.4900(6) 0.0482(3) 0.3079(3) 0.0575(6) Uani 1 1 d . . .
H1 H 0.4125 -0.0179 0.3969 0.069 Uiso 1 1 calc R . .
C2 C 0.7061(6) 0.0017(3) 0.2440(3) 0.0541(6) Uani 1 1 d . . .
H2 H 0.7735 -0.0928 0.2901 0.065 Uiso 1 1 calc R . .
C6 C 1.0505(5) 0.0469(3) 0.0333(3) 0.0526(6) Uani 1 1 d . . .
H6A H 1.1732 -0.0109 0.0984 0.063 Uiso 1 1 calc R . .
H6B H 1.1480 0.1340 -0.0392 0.063 Uiso 1 1 calc R . .
C5 C 0.4987(6) 0.2714(3) 0.1229(3) 0.0634(7) Uani 1 1 d . . .
H5 H 0.4277 0.3655 0.0797 0.076 Uiso 1 1 calc R . .
C4 C 0.7138(6) 0.2347(3) 0.0503(3) 0.0567(6) Uani 1 1 d . . .
H4 H 0.7852 0.3030 -0.0390 0.068 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
I1 0.04252(12) 0.05610(14) 0.06225(14) -0.03689(10) -0.00163(7) 0.00368(7)
F2 0.0858(11) 0.0780(11) 0.0399(7) -0.0226(7) -0.0005(7) 0.0198(9)
F1 0.0824(11) 0.0676(10) 0.0559(9) -0.0208(8) -0.0181(8) 0.0326(8)
N1 0.0512(12) 0.0678(15) 0.0623(14) -0.0408(12) -0.0003(10) 0.0056(10)
C8 0.0378(12) 0.0451(13) 0.0491(13) -0.0260(11) -0.0021(9) 0.0018(9)
C9 0.0515(13) 0.0500(14) 0.0383(12) -0.0210(11) 0.0000(9) 0.0005(10)
C7 0.0476(13) 0.0458(13) 0.0448(12) -0.0199(11) -0.0095(10) 0.0084(10)
C3 0.0441(13) 0.0549(14) 0.0487(12) -0.0323(11) -0.0075(10) 0.0075(10)
C1 0.0630(16) 0.0621(17) 0.0478(13) -0.0269(13) 0.0050(11) -0.0036(13)
C2 0.0615(16) 0.0491(15) 0.0498(13) -0.0206(12) -0.0046(11) 0.0082(11)
C6 0.0447(13) 0.0649(17) 0.0582(14) -0.0370(13) -0.0045(10) 0.0080(11)
C5 0.0656(17) 0.0582(17) 0.0689(18) -0.0309(15) -0.0096(14) 0.0210(13)
C4 0.0628(16) 0.0569(16) 0.0467(13) -0.0208(12) -0.0017(11) 0.0097(12)

_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 C8 2.106(2) . ?
F2 C9 1.343(3) . ?
F1 C7 1.347(3) . ?
N1 C1 1.322(4) . ?
N1 C5 1.319(4) . ?
C8 C9 1.373(3) . ?
C8 C7 1.384(3) . ?
C9 C7 1.370(3) 2_466 ?
C7 C9 1.370(3) 2_466 ?
C3 C2 1.383(4) . ?
C3 C6 1.507(3) . ?
C3 C4 1.373(4) . ?
C1 H1 0.9300 . ?
C1 C2 1.373(4) . ?
C2 H2 0.9300 . ?
C6 C6 1.524(5) 2_755 ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C5 H5 0.9300 . ?
C5 C4 1.372(4) . ?
C4 H4 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 N1 C1 116.4(2) . . ?
C9 C8 I1 121.40(17) . . ?
C9 C8 C7 116.5(2) . . ?
C7 C8 I1 122.11(17) . . ?
F2 C9 C8 119.4(2) . . ?
F2 C9 C7 118.6(2) . 2_466 ?
C7 C9 C8 121.9(2) 2_466 . ?
F1 C7 C8 119.9(2) . . ?
F1 C7 C9 118.4(2) . 2_466 ?
C9 C7 C8 121.6(2) 2_466 . ?
C2 C3 C6 121.4(2) . . ?
C4 C3 C2 116.6(2) . . ?
C4 C3 C6 121.9(2) . . ?
N1 C1 H1 118.2 . . ?
N1 C1 C2 123.6(2) . . ?
C2 C1 H1 118.2 . . ?
C3 C2 H2 120.2 . . ?
C1 C2 C3 119.6(2) . . ?
C1 C2 H2 120.2 . . ?
C3 C6 C6 111.5(3) . 2_755 ?
C3 C6 H6A 109.3 . . ?
C3 C6 H6B 109.3 . . ?
C6 C6 H6A 109.3 2_755 . ?
C6 C6 H6B 109.3 2_755 . ?
H6A C6 H6B 108.0 . . ?
N1 C5 H5 117.9 . . ?
N1 C5 C4 124.2(3) . . ?
C4 C5 H5 117.9 . . ?
C3 C4 H4 120.3 . . ?
C5 C4 C3 119.5(2) . . ?
C5 C4 H4 120.3 . . ?

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 C8 C9 F2 -0.9(3) . . . . ?
I1 C8 C9 C7 177.50(19) . . . 2_466 ?
I1 C8 C7 F1 3.3(3) . . . . ?
I1 C8 C7 C9 -177.49(19) . . . 2_466 ?
N1 C1 C2 C3 -1.2(4) . . . . ?
N1 C5 C4 C3 0.4(5) . . . . ?
C9 C8 C7 F1 -178.3(2) . . . . ?
C9 C8 C7 C9 0.9(4) . . . 2_466 ?
C7 C8 C9 F2 -179.3(2) . . . . ?
C7 C8 C9 C7 -0.9(4) . . . 2_466 ?
C1 N1 C5 C4 -0.6(5) . . . . ?
C2 C3 C6 C6 80.1(4) . . . 2_755 ?
C2 C3 C4 C5 -0.4(4) . . . . ?
C6 C3 C2 C1 -176.7(2) . . . . ?
C6 C3 C4 C5 177.0(3) . . . . ?
C5 N1 C1 C2 1.1(4) . . . . ?
C4 C3 C2 C1 0.9(4) . . . . ?
C4 C3 C6 C6 -97.3(4) . . . 2_755 ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_Cocrystal_1_shear_induced_daughter_domain
_database_code_depnum_ccdc_archive 'CCDC 2256405'
loop_
_audit_author_name
_audit_author_address
'Subham Ranjan'
;Yokohama City University
Japan
;
_audit_update_record             
;
2023-04-14 deposited with the CCDC.	2023-10-16 downloaded from the CCDC.
;
_audit_creation_date             2023-04-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C3 F2 I, C6 H6 N'
_chemical_formula_sum            'C9 H6 F2 I N'
_chemical_formula_weight         293.05
_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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   5.03720(10)
_cell_length_b                   9.9139(3)
_cell_length_c                   10.6213(3)
_cell_angle_alpha                64.7660(10)
_cell_angle_beta                 82.1070(10)
_cell_angle_gamma                87.9050(10)
_cell_volume                     475.11(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7309
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.73
_cell_measurement_theta_min      2.27
_exptl_absorpt_coefficient_mu    3.351
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.4381
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;

_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.048
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             276
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8594
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         2.14
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean 7.391
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'graphite monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         0
_reflns_number_gt                1578
_reflns_number_total             1648
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'APEX3 v2019.11 (Bruker AXS Inc., 2019)'
_computing_data_collection       'Bruker Instrument Service (Bruker AXS Inc.)'
_computing_data_reduction        'SAINT (Bruker AXS Inc.)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2013)'
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       0.0151(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         1648
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0177
_refine_ls_R_factor_gt           0.0162
_refine_ls_restrained_S_all      1.118
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0031P)²+0.1918P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0362
_refine_ls_wR_factor_ref         0.0366
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C4(H4), C2(H2), C1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I -0.00730(3) 0.312665(17) 0.371504(18) 0.04992(9) Uani 1 1 d . . .
F1 F -0.3774(3) 0.58766(19) 0.22033(15) 0.0700(5) Uani 1 1 d . . .
F2 F -0.2402(3) 0.27464(18) 0.68480(16) 0.0700(5) Uani 1 1 d . . .
N1 N 0.3863(4) 0.1818(3) 0.2497(3) 0.0564(6) Uani 1 1 d . . .
C8 C -0.2984(5) 0.4264(3) 0.4494(3) 0.0429(5) Uani 1 1 d . . .
C7 C -0.4340(5) 0.5432(3) 0.3596(2) 0.0450(5) Uani 1 1 d . . .
C9 C -0.3691(5) 0.3854(3) 0.5906(3) 0.0450(5) Uani 1 1 d . . .
C3 C 0.8231(5) 0.0959(3) 0.1108(3) 0.0448(5) Uani 1 1 d . . .
C5 C 0.4905(6) 0.0487(3) 0.3079(3) 0.0574(7) Uani 1 1 d . . .
H5 H 0.4139 -0.0171 0.3973 0.069 Uiso 1 1 calc R . .
C4 C 0.7068(5) 0.0020(3) 0.2433(3) 0.0545(6) Uani 1 1 d . . .
H4 H 0.7738 -0.0927 0.2893 0.065 Uiso 1 1 calc R . .
C6 C 1.0504(5) 0.0471(3) 0.0333(3) 0.0516(6) Uani 1 1 d . . .
H6A H 1.1737 -0.0105 0.0980 0.062 Uiso 1 1 calc R . .
H6B H 1.1474 0.1344 -0.0394 0.062 Uiso 1 1 calc R . .
C2 C 0.7141(6) 0.2349(3) 0.0499(3) 0.0559(7) Uani 1 1 d . . .
H2 H 0.7850 0.3031 -0.0396 0.067 Uiso 1 1 calc R . .
C1 C 0.4988(6) 0.2713(3) 0.1234(3) 0.0627(7) Uani 1 1 d . . .
H1 H 0.4284 0.3656 0.0806 0.075 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
I1 0.04234(12) 0.05586(13) 0.06243(14) -0.03722(9) -0.00183(7) 0.00368(7)
F1 0.0851(11) 0.0791(10) 0.0388(8) -0.0220(8) -0.0013(7) 0.0207(9)
F2 0.0840(11) 0.0676(10) 0.0543(9) -0.0217(8) -0.0189(8) 0.0343(9)
N1 0.0496(13) 0.0678(14) 0.0631(15) -0.0408(12) -0.0009(10) 0.0052(11)
C8 0.0393(12) 0.0451(12) 0.0483(14) -0.0252(11) -0.0012(10) 0.0022(10)
C7 0.0502(14) 0.0481(13) 0.0378(13) -0.0208(11) -0.0015(10) 0.0020(10)
C9 0.0462(13) 0.0443(12) 0.0454(14) -0.0195(11) -0.0093(10) 0.0079(10)
C3 0.0427(13) 0.0537(14) 0.0484(14) -0.0318(12) -0.0073(10) 0.0065(10)
C5 0.0618(17) 0.0614(16) 0.0497(15) -0.0275(13) 0.0039(12) -0.0018(13)
C4 0.0615(16) 0.0487(14) 0.0532(16) -0.0223(12) -0.0073(12) 0.0098(12)
C6 0.0437(13) 0.0635(15) 0.0573(16) -0.0364(13) -0.0029(11) 0.0061(11)
C2 0.0625(17) 0.0548(15) 0.0451(15) -0.0189(12) -0.0006(12) 0.0088(12)
C1 0.0667(18) 0.0572(16) 0.0664(19) -0.0299(15) -0.0095(14) 0.0233(14)

_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 C8 2.109(2) . ?
F1 C7 1.342(3) . ?
F2 C9 1.348(3) . ?
N1 C5 1.320(3) . ?
N1 C1 1.312(4) . ?
C8 C7 1.377(3) . ?
C8 C9 1.374(3) . ?
C7 C9 1.374(3) 2_466 ?
C9 C7 1.374(3) 2_466 ?
C3 C4 1.374(4) . ?
C3 C6 1.505(3) . ?
C3 C2 1.378(3) . ?
C5 H5 0.9300 . ?
C5 C4 1.379(4) . ?
C4 H4 0.9300 . ?
C6 C6 1.525(5) 2_755 ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C2 H2 0.9300 . ?
C2 C1 1.376(4) . ?
C1 H1 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C5 116.5(2) . . ?
C7 C8 I1 120.94(17) . . ?
C9 C8 I1 122.27(17) . . ?
C9 C8 C7 116.8(2) . . ?
F1 C7 C8 119.8(2) . . ?
F1 C7 C9 118.7(2) . 2_466 ?
C9 C7 C8 121.4(2) 2_466 . ?
F2 C9 C8 120.2(2) . . ?
F2 C9 C7 118.0(2) . 2_466 ?
C7 C9 C8 121.8(2) 2_466 . ?
C4 C3 C6 121.6(2) . . ?
C4 C3 C2 116.8(2) . . ?
C2 C3 C6 121.6(2) . . ?
N1 C5 H5 118.3 . . ?
N1 C5 C4 123.5(3) . . ?
C4 C5 H5 118.3 . . ?
C3 C4 C5 119.7(2) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C3 C6 C6 111.5(3) . 2_755 ?
C3 C6 H6A 109.3 . . ?
C3 C6 H6B 109.3 . . ?
C6 C6 H6A 109.3 2_755 . ?
C6 C6 H6B 109.3 2_755 . ?
H6A C6 H6B 108.0 . . ?
C3 C2 H2 120.5 . . ?
C1 C2 C3 119.1(2) . . ?
C1 C2 H2 120.5 . . ?
N1 C1 C2 124.4(2) . . ?
N1 C1 H1 117.8 . . ?
C2 C1 H1 117.8 . . ?

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 C8 C7 F1 -1.2(3) . . . . ?
I1 C8 C7 C9 177.60(19) . . . 2_466 ?
I1 C8 C9 F2 4.0(3) . . . . ?
I1 C8 C9 C7 -177.57(19) . . . 2_466 ?
N1 C5 C4 C3 -0.6(4) . . . . ?
C7 C8 C9 F2 -178.2(2) . . . . ?
C7 C8 C9 C7 0.2(4) . . . 2_466 ?
C9 C8 C7 F1 -179.1(2) . . . . ?
C9 C8 C7 C9 -0.2(4) . . . 2_466 ?
C3 C2 C1 N1 -0.1(5) . . . . ?
C5 N1 C1 C2 0.1(5) . . . . ?
C4 C3 C6 C6 79.9(4) . . . 2_755 ?
C4 C3 C2 C1 -0.1(4) . . . . ?
C6 C3 C4 C5 -176.9(2) . . . . ?
C6 C3 C2 C1 177.2(3) . . . . ?
C2 C3 C4 C5 0.5(4) . . . . ?
C2 C3 C6 C6 -97.3(4) . . . 2_755 ?
C1 N1 C5 C4 0.3(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_Cocrystal_2_shear_induced_daughter_domain
_database_code_depnum_ccdc_archive 'CCDC 2256407'
loop_
_audit_author_name
_audit_author_address
'Subham Ranjan'
;Yokohama City University
Japan
;
_audit_update_record             
;
2023-04-14 deposited with the CCDC.	2023-10-16 downloaded from the CCDC.
;
_audit_creation_date             2023-04-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C6 F4 I2, C16 H10'
_chemical_formula_sum            'C22 H10 F4 I2'
_chemical_formula_weight         604.10
_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'

_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'

_cell_length_a                   8.3940(7)
_cell_length_b                   18.3051(13)
_cell_length_c                   13.1815(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.310(2)
_cell_angle_gamma                90.00
_cell_volume                     1953.5(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7807
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.274
_cell_measurement_theta_min      2.225
_exptl_absorpt_coefficient_mu    3.261
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.2429
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.054
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0815
_diffrn_reflns_av_unetI/netI     0.0535
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            34044
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         1.95
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean 7.391
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'graphite monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2728
_reflns_number_total             4433
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'APEX3 v2019.11 (Bruker AXS Inc., 2019)'
_computing_data_collection       'Bruker Instrument Service (Bruker AXS Inc.)'
_computing_data_reduction        'SAINT (Bruker AXS Inc.)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2013)'
_refine_diff_density_max         1.295
_refine_diff_density_min         -0.812
_refine_diff_density_rms         0.091
_refine_ls_extinction_coef       0.0065(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         4433
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0951
_refine_ls_R_factor_gt           0.0460
_refine_ls_restrained_S_all      1.014
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0408P)²+3.5075P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0976
_refine_ls_wR_factor_ref         0.1117
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C14(H14), C15(H15), C8(H8), C7(H7), C12(H12), C17(H17), C10(H10), C19(H19),
 C18(H18), C11(H11)
;
_atom_sites_solution_hydrogens   geom
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 1.05698(5) 0.53917(2) 0.76384(4) 0.0770(2) Uani 1 1 d . . .
I2 I 0.70079(6) 0.20101(2) 0.79979(4) 0.0830(2) Uani 1 1 d . . .
F4 F 1.0731(5) 0.4320(2) 0.9571(3) 0.0871(11) Uani 1 1 d . . .
F3 F 0.9354(5) 0.30386(19) 0.9713(3) 0.0882(11) Uani 1 1 d . . .
F1 F 0.8212(5) 0.4371(2) 0.5941(3) 0.0921(12) Uani 1 1 d . . .
F2 F 0.6832(5) 0.3090(2) 0.6080(3) 0.0968(12) Uani 1 1 d . . .
C21 C 0.5690(6) 0.5759(3) 0.2400(4) 0.0489(12) Uani 1 1 d . . .
C22 C 0.6379(6) 0.6421(3) 0.2139(4) 0.0469(12) Uani 1 1 d . . .
C20 C 0.6168(7) 0.5491(3) 0.3435(4) 0.0530(13) Uani 1 1 d . . .
C4 C 0.8043(6) 0.3028(3) 0.7901(5) 0.0539(13) Uani 1 1 d . . .
C1 C 0.9511(6) 0.4385(3) 0.7758(5) 0.0531(13) Uani 1 1 d . . .
C9 C 0.7544(7) 0.6815(3) 0.2913(4) 0.0560(13) Uani 1 1 d . . .
C6 C 0.9764(7) 0.4026(3) 0.8698(4) 0.0579(14) Uani 1 1 d . . .
C5 C 0.9047(7) 0.3363(3) 0.8768(4) 0.0575(14) Uani 1 1 d . . .
C16 C 0.4545(6) 0.5366(3) 0.1611(5) 0.0543(13) Uani 1 1 d . . .
C13 C 0.5915(7) 0.6678(3) 0.1090(4) 0.0543(13) Uani 1 1 d . . .
C14 C 0.4734(7) 0.6267(4) 0.0323(5) 0.0674(16) Uani 1 1 d . . .
H14 H 0.4411 0.6433 -0.0368 0.081 Uiso 1 1 calc R . .
C2 C 0.8503(7) 0.4050(3) 0.6891(4) 0.0594(14) Uani 1 1 d . . .
C15 C 0.4087(7) 0.5650(4) 0.0575(5) 0.0677(16) Uani 1 1 d . . .
H15 H 0.3313 0.5399 0.0057 0.081 Uiso 1 1 calc R . .
C8 C 0.8016(8) 0.6529(4) 0.3956(5) 0.0716(17) Uani 1 1 d . . .
H8 H 0.8798 0.6776 0.4474 0.086 Uiso 1 1 calc R . .
C3 C 0.7782(7) 0.3388(3) 0.6963(5) 0.0617(15) Uani 1 1 d . . .
C7 C 0.7351(8) 0.5907(3) 0.4207(4) 0.0667(16) Uani 1 1 d . . .
H7 H 0.7665 0.5743 0.4898 0.080 Uiso 1 1 calc R . .
C12 C 0.6605(8) 0.7321(3) 0.0840(5) 0.0722(17) Uani 1 1 d . . .
H12 H 0.6305 0.7495 0.0152 0.087 Uiso 1 1 calc R . .
C17 C 0.3913(7) 0.4708(3) 0.1894(6) 0.0710(17) Uani 1 1 d . . .
H17 H 0.3171 0.4436 0.1385 0.085 Uiso 1 1 calc R . .
C10 C 0.8201(7) 0.7459(3) 0.2627(6) 0.0684(16) Uani 1 1 d . . .
H10 H 0.8961 0.7725 0.3132 0.082 Uiso 1 1 calc R . .
C19 C 0.5486(8) 0.4842(3) 0.3673(5) 0.0686(16) Uani 1 1 d . . .
H19 H 0.5785 0.4664 0.4358 0.082 Uiso 1 1 calc R . .
C18 C 0.4378(8) 0.4464(3) 0.2908(6) 0.0711(17) Uani 1 1 d . . .
H18 H 0.3932 0.4031 0.3081 0.085 Uiso 1 1 calc R . .
C11 C 0.7737(8) 0.7702(4) 0.1608(6) 0.0759(18) Uani 1 1 d . . .
H11 H 0.8191 0.8132 0.1432 0.091 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
I1 0.0609(3) 0.0496(2) 0.1238(4) 0.0074(2) 0.0300(2) 0.00325(17)
I2 0.0828(3) 0.0474(2) 0.1322(5) -0.0082(2) 0.0519(3) -0.00286(19)
F4 0.093(3) 0.083(2) 0.072(2) -0.0153(19) -0.002(2) -0.006(2)
F3 0.112(3) 0.078(2) 0.071(2) 0.0208(19) 0.019(2) 0.011(2)
F1 0.094(3) 0.102(3) 0.071(2) 0.031(2) 0.006(2) 0.006(2)
F2 0.094(3) 0.102(3) 0.078(3) -0.018(2) -0.006(2) -0.020(2)
C21 0.044(3) 0.050(3) 0.057(3) -0.001(2) 0.019(2) 0.018(2)
C22 0.045(3) 0.046(3) 0.051(3) -0.007(2) 0.014(2) 0.010(2)
C20 0.054(3) 0.054(3) 0.053(3) 0.009(2) 0.017(2) 0.016(3)
C4 0.047(3) 0.042(3) 0.074(4) -0.003(3) 0.019(3) 0.005(2)
C1 0.044(3) 0.039(3) 0.074(4) 0.003(3) 0.013(3) 0.006(2)
C9 0.056(3) 0.050(3) 0.063(4) -0.010(3) 0.018(3) 0.007(2)
C6 0.053(3) 0.054(3) 0.059(4) -0.009(3) 0.002(3) 0.007(3)
C5 0.065(4) 0.045(3) 0.063(4) 0.003(3) 0.018(3) 0.013(3)
C16 0.043(3) 0.043(3) 0.079(4) -0.007(3) 0.020(3) 0.008(2)
C13 0.050(3) 0.050(3) 0.065(4) 0.003(3) 0.019(3) 0.012(2)
C14 0.065(4) 0.082(4) 0.052(3) 0.004(3) 0.009(3) 0.018(3)
C2 0.050(3) 0.065(4) 0.062(4) 0.010(3) 0.010(3) 0.012(3)
C15 0.054(4) 0.077(4) 0.062(4) -0.015(3) -0.001(3) 0.011(3)
C8 0.070(4) 0.078(4) 0.061(4) -0.021(3) 0.008(3) 0.004(3)
C3 0.052(3) 0.065(4) 0.063(4) -0.010(3) 0.005(3) 0.002(3)
C7 0.080(4) 0.075(4) 0.041(3) -0.005(3) 0.008(3) 0.011(3)
C12 0.068(4) 0.069(4) 0.086(5) 0.019(3) 0.031(4) 0.022(3)
C17 0.055(3) 0.052(3) 0.102(5) -0.016(3) 0.016(3) 0.004(3)
C10 0.055(4) 0.058(4) 0.091(5) -0.013(3) 0.018(3) -0.006(3)
C19 0.077(4) 0.065(4) 0.071(4) 0.019(3) 0.033(3) 0.019(3)
C18 0.065(4) 0.051(3) 0.105(5) 0.014(4) 0.034(4) 0.013(3)
C11 0.066(4) 0.060(4) 0.108(6) 0.000(4) 0.035(4) 0.003(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 C1 2.070(5) . ?
I2 C4 2.075(5) . ?
F4 C6 1.334(6) . ?
F3 C5 1.342(6) . ?
F1 C2 1.347(6) . ?
F2 C3 1.342(6) . ?
C21 C22 1.424(7) . ?
C21 C20 1.406(7) . ?
C21 C16 1.412(7) . ?
C22 C9 1.411(7) . ?
C22 C13 1.414(7) . ?
C20 C7 1.438(8) . ?
C20 C19 1.390(8) . ?
C4 C5 1.372(8) . ?
C4 C3 1.367(8) . ?
C1 C6 1.369(8) . ?
C1 C2 1.374(8) . ?
C9 C8 1.427(8) . ?
C9 C10 1.394(8) . ?
C6 C5 1.368(8) . ?
C16 C15 1.415(8) . ?
C16 C17 1.406(8) . ?
C13 C14 1.430(8) . ?
C13 C12 1.389(8) . ?
C14 H14 0.9300 . ?
C14 C15 1.332(8) . ?
C2 C3 1.368(8) . ?
C15 H15 0.9300 . ?
C8 H8 0.9300 . ?
C8 C7 1.346(9) . ?
C7 H7 0.9300 . ?
C12 H12 0.9300 . ?
C12 C11 1.382(9) . ?
C17 H17 0.9300 . ?
C17 C18 1.364(9) . ?
C10 H10 0.9300 . ?
C10 C11 1.370(9) . ?
C19 H19 0.9300 . ?
C19 C18 1.366(9) . ?
C18 H18 0.9300 . ?
C11 H11 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C20 C21 C22 120.1(5) . . ?
C20 C21 C16 120.1(5) . . ?
C16 C21 C22 119.8(5) . . ?
C9 C22 C21 120.6(5) . . ?
C9 C22 C13 119.7(5) . . ?
C13 C22 C21 119.7(5) . . ?
C21 C20 C7 117.9(5) . . ?
C19 C20 C21 119.3(5) . . ?
C19 C20 C7 122.8(5) . . ?
C5 C4 I2 121.7(4) . . ?
C3 C4 I2 121.3(4) . . ?
C3 C4 C5 117.0(5) . . ?
C6 C1 I1 122.0(4) . . ?
C6 C1 C2 116.9(5) . . ?
C2 C1 I1 121.1(4) . . ?
C22 C9 C8 118.2(5) . . ?
C10 C9 C22 119.0(5) . . ?
C10 C9 C8 122.8(6) . . ?
F4 C6 C1 120.0(5) . . ?
F4 C6 C5 118.6(5) . . ?
C5 C6 C1 121.4(5) . . ?
F3 C5 C4 120.0(5) . . ?
F3 C5 C6 118.4(5) . . ?
C6 C5 C4 121.6(5) . . ?
C21 C16 C15 118.8(5) . . ?
C17 C16 C21 118.1(5) . . ?
C17 C16 C15 123.0(6) . . ?
C22 C13 C14 118.5(5) . . ?
C12 C13 C22 119.3(5) . . ?
C12 C13 C14 122.2(6) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 C13 121.5(5) . . ?
C15 C14 H14 119.3 . . ?
F1 C2 C1 119.9(5) . . ?
F1 C2 C3 118.4(5) . . ?
C3 C2 C1 121.6(5) . . ?
C16 C15 H15 119.1 . . ?
C14 C15 C16 121.8(5) . . ?
C14 C15 H15 119.1 . . ?
C9 C8 H8 119.4 . . ?
C7 C8 C9 121.3(5) . . ?
C7 C8 H8 119.4 . . ?
F2 C3 C4 120.4(5) . . ?
F2 C3 C2 118.2(5) . . ?
C2 C3 C4 121.4(5) . . ?
C20 C7 H7 119.1 . . ?
C8 C7 C20 121.9(5) . . ?
C8 C7 H7 119.1 . . ?
C13 C12 H12 119.9 . . ?
C11 C12 C13 120.2(6) . . ?
C11 C12 H12 119.9 . . ?
C16 C17 H17 119.7 . . ?
C18 C17 C16 120.7(6) . . ?
C18 C17 H17 119.7 . . ?
C9 C10 H10 119.7 . . ?
C11 C10 C9 120.7(6) . . ?
C11 C10 H10 119.7 . . ?
C20 C19 H19 119.8 . . ?
C18 C19 C20 120.4(6) . . ?
C18 C19 H19 119.8 . . ?
C17 C18 C19 121.4(6) . . ?
C17 C18 H18 119.3 . . ?
C19 C18 H18 119.3 . . ?
C12 C11 H11 119.5 . . ?
C10 C11 C12 121.1(6) . . ?
C10 C11 H11 119.5 . . ?

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
I1 C1 C6 F4 -0.7(7) . . . . ?
I1 C1 C6 C5 179.5(4) . . . . ?
I1 C1 C2 F1 1.1(7) . . . . ?
I1 C1 C2 C3 -179.3(4) . . . . ?
I2 C4 C5 F3 -1.4(7) . . . . ?
I2 C4 C5 C6 178.2(4) . . . . ?
I2 C4 C3 F2 0.6(7) . . . . ?
I2 C4 C3 C2 -178.0(4) . . . . ?
F4 C6 C5 F3 -0.2(8) . . . . ?
F4 C6 C5 C4 -179.8(5) . . . . ?
F1 C2 C3 F2 0.6(8) . . . . ?
F1 C2 C3 C4 179.2(5) . . . . ?
C21 C22 C9 C8 0.5(7) . . . . ?
C21 C22 C9 C10 179.6(5) . . . . ?
C21 C22 C13 C14 1.1(7) . . . . ?
C21 C22 C13 C12 -179.4(5) . . . . ?
C21 C20 C7 C8 -1.2(8) . . . . ?
C21 C20 C19 C18 0.8(8) . . . . ?
C21 C16 C15 C14 1.6(8) . . . . ?
C21 C16 C17 C18 1.0(8) . . . . ?
C22 C21 C20 C7 0.4(7) . . . . ?
C22 C21 C20 C19 -179.7(5) . . . . ?
C22 C21 C16 C15 -1.1(7) . . . . ?
C22 C21 C16 C17 178.9(4) . . . . ?
C22 C9 C8 C7 -1.2(8) . . . . ?
C22 C9 C10 C11 -0.7(8) . . . . ?
C22 C13 C14 C15 -0.6(8) . . . . ?
C22 C13 C12 C11 0.2(8) . . . . ?
C20 C21 C22 C9 -0.1(7) . . . . ?
C20 C21 C22 C13 178.7(4) . . . . ?
C20 C21 C16 C15 180.0(5) . . . . ?
C20 C21 C16 C17 -0.1(7) . . . . ?
C20 C19 C18 C17 0.1(9) . . . . ?
C1 C6 C5 F3 179.6(5) . . . . ?
C1 C6 C5 C4 0.0(8) . . . . ?
C1 C2 C3 F2 -179.1(5) . . . . ?
C1 C2 C3 C4 -0.5(9) . . . . ?
C9 C22 C13 C14 179.9(5) . . . . ?
C9 C22 C13 C12 -0.6(7) . . . . ?
C9 C8 C7 C20 1.6(9) . . . . ?
C9 C10 C11 C12 0.3(9) . . . . ?
C6 C1 C2 F1 -179.5(5) . . . . ?
C6 C1 C2 C3 0.1(8) . . . . ?
C5 C4 C3 F2 179.2(5) . . . . ?
C5 C4 C3 C2 0.6(8) . . . . ?
C16 C21 C22 C9 -179.0(4) . . . . ?
C16 C21 C22 C13 -0.2(7) . . . . ?
C16 C21 C20 C7 179.3(5) . . . . ?
C16 C21 C20 C19 -0.8(7) . . . . ?
C16 C17 C18 C19 -1.0(9) . . . . ?
C13 C22 C9 C8 -178.3(5) . . . . ?
C13 C22 C9 C10 0.8(7) . . . . ?
C13 C14 C15 C16 -0.7(9) . . . . ?
C13 C12 C11 C10 0.0(9) . . . . ?
C14 C13 C12 C11 179.7(5) . . . . ?
C2 C1 C6 F4 179.9(5) . . . . ?
C2 C1 C6 C5 0.1(8) . . . . ?
C15 C16 C17 C18 -179.1(5) . . . . ?
C8 C9 C10 C11 178.5(6) . . . . ?
C3 C4 C5 F3 -179.9(5) . . . . ?
C3 C4 C5 C6 -0.3(8) . . . . ?
C7 C20 C19 C18 -179.4(5) . . . . ?
C12 C13 C14 C15 179.8(5) . . . . ?
C17 C16 C15 C14 -178.4(6) . . . . ?
C10 C9 C8 C7 179.7(6) . . . . ?
C19 C20 C7 C8 179.0(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_Cocrystal_2_mother_domain
_database_code_depnum_ccdc_archive 'CCDC 2256406'
loop_
_audit_author_name
_audit_author_address
'Subham Ranjan'
;Yokohama City University
Japan
;
_audit_update_record             
;
2023-04-14 deposited with the CCDC.	2023-10-16 downloaded from the CCDC.
;
_audit_creation_date             2023-04-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C6 F4 I2, C16 H10'
_chemical_formula_sum            'C22 H10 F4 I2'
_chemical_formula_weight         604.10
_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'

_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'

_cell_length_a                   8.3909(5)
_cell_length_b                   18.3230(11)
_cell_length_c                   13.1994(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.330(2)
_cell_angle_gamma                90.00
_cell_volume                     1957.2(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9981
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.16
_cell_measurement_theta_min      2.22
_exptl_absorpt_coefficient_mu    3.255
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.1310
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;

_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.050
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0609
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            35875
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         1.95
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean 7.391
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'graphite monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         0
_reflns_number_gt                2766
_reflns_number_total             3442
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'APEX3 v2019.11 (Bruker AXS Inc., 2019)'
_computing_data_collection       'Bruker Instrument Service (Bruker AXS Inc.)'
_computing_data_reduction        'SAINT (Bruker AXS Inc.)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2013)'
_refine_diff_density_max         0.884
_refine_diff_density_min         -1.210
_refine_diff_density_rms         0.109
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3442
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0490
_refine_ls_R_factor_gt           0.0359
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0334P)²+3.3283P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0834
_refine_ls_wR_factor_ref         0.0894
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C14(H14), C12(H12), C15(H15), C7(H7), C8(H8), C17(H17), C19(H19), C10(H10),
 C18(H18), C11(H11)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I -0.05698(4) 0.460833(19) 0.23617(4) 0.07546(16) Uani 1 1 d . . .
I2 I 0.29917(5) 0.798991(19) 0.20016(4) 0.08164(17) Uani 1 1 d . . .
F4 F -0.0736(4) 0.56794(18) 0.0426(2) 0.0848(9) Uani 1 1 d . . .
F3 F 0.0645(5) 0.69622(18) 0.0286(2) 0.0854(10) Uani 1 1 d . . .
F1 F 0.1786(4) 0.5629(2) 0.4057(2) 0.0896(10) Uani 1 1 d . . .
F2 F 0.3174(5) 0.6914(2) 0.3917(3) 0.0945(11) Uani 1 1 d . . .
C21 C 0.4303(5) 0.4237(2) 0.7600(3) 0.0446(10) Uani 1 1 d . . .
C22 C 0.3621(5) 0.3579(2) 0.7863(3) 0.0461(10) Uani 1 1 d . . .
C1 C 0.0492(6) 0.5616(2) 0.2242(4) 0.0524(11) Uani 1 1 d . . .
C13 C 0.4089(6) 0.3320(3) 0.8914(4) 0.0539(11) Uani 1 1 d . . .
C6 C 0.0235(6) 0.5976(3) 0.1299(4) 0.0556(12) Uani 1 1 d . . .
C4 C 0.1952(6) 0.6971(2) 0.2093(4) 0.0537(11) Uani 1 1 d . . .
C5 C 0.0952(6) 0.6637(3) 0.1230(4) 0.0558(12) Uani 1 1 d . . .
C16 C 0.5460(6) 0.4634(2) 0.8389(4) 0.0527(11) Uani 1 1 d . . .
C9 C 0.2451(6) 0.3184(3) 0.7082(4) 0.0548(12) Uani 1 1 d . . .
C2 C 0.1504(6) 0.5954(3) 0.3110(4) 0.0579(12) Uani 1 1 d . . .
C20 C 0.3834(6) 0.4506(3) 0.6551(4) 0.0553(12) Uani 1 1 d . . .
C14 C 0.5271(7) 0.3733(3) 0.9677(4) 0.0658(14) Uani 1 1 d . . .
H14 H 0.5601 0.3564 1.0365 0.079 Uiso 1 1 calc R . .
C12 C 0.3384(7) 0.2675(3) 0.9166(5) 0.0677(14) Uani 1 1 d . . .
H12 H 0.3675 0.2502 0.9853 0.081 Uiso 1 1 calc R . .
C3 C 0.2220(6) 0.6616(3) 0.3040(4) 0.0612(13) Uani 1 1 d . . .
C15 C 0.5913(6) 0.4351(3) 0.9431(4) 0.0660(14) Uani 1 1 d . . .
H15 H 0.6676 0.4604 0.9952 0.079 Uiso 1 1 calc R . .
C7 C 0.2647(7) 0.4092(3) 0.5793(4) 0.0666(14) Uani 1 1 d . . .
H7 H 0.2317 0.4258 0.5103 0.080 Uiso 1 1 calc R . .
C8 C 0.1993(7) 0.3470(3) 0.6043(4) 0.0692(14) Uani 1 1 d . . .
H8 H 0.1220 0.3220 0.5524 0.083 Uiso 1 1 calc R . .
C17 C 0.6089(7) 0.5288(3) 0.8112(5) 0.0673(14) Uani 1 1 d . . .
H17 H 0.6833 0.5557 0.8622 0.081 Uiso 1 1 calc R . .
C19 C 0.4513(7) 0.5154(3) 0.6326(4) 0.0670(14) Uani 1 1 d . . .
H19 H 0.4213 0.5334 0.5643 0.080 Uiso 1 1 calc R . .
C10 C 0.1807(6) 0.2536(3) 0.7380(5) 0.0685(14) Uani 1 1 d . . .
H10 H 0.1056 0.2265 0.6876 0.082 Uiso 1 1 calc R . .
C18 C 0.5626(7) 0.5538(3) 0.7098(5) 0.0709(15) Uani 1 1 d . . .
H18 H 0.6068 0.5972 0.6928 0.085 Uiso 1 1 calc R . .
C11 C 0.2261(7) 0.2296(3) 0.8396(5) 0.0730(15) Uani 1 1 d . . .
H11 H 0.1802 0.1868 0.8571 0.088 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
I1 0.0617(2) 0.0508(2) 0.1173(4) 0.00749(19) 0.0297(2) 0.00322(15)
I2 0.0847(3) 0.0485(2) 0.1256(4) -0.0084(2) 0.0522(3) -0.00267(17)
F4 0.094(2) 0.082(2) 0.0665(19) -0.0171(17) 0.0003(18) -0.0067(18)
F3 0.111(3) 0.082(2) 0.0627(19) 0.0215(16) 0.0207(18) 0.0131(19)
F1 0.096(2) 0.102(3) 0.0631(19) 0.0306(18) 0.0079(17) 0.008(2)
F2 0.095(2) 0.103(3) 0.070(2) -0.0184(19) -0.0041(19) -0.021(2)
C21 0.045(2) 0.045(2) 0.046(3) -0.0027(19) 0.016(2) 0.0126(19)
C22 0.046(2) 0.045(2) 0.049(3) -0.005(2) 0.015(2) 0.0105(19)
C1 0.048(3) 0.043(2) 0.066(3) 0.005(2) 0.014(2) 0.0081(19)
C13 0.053(3) 0.053(3) 0.059(3) 0.006(2) 0.021(2) 0.014(2)
C6 0.053(3) 0.052(3) 0.056(3) -0.009(2) 0.004(2) 0.007(2)
C4 0.051(3) 0.043(2) 0.070(3) 0.000(2) 0.020(2) 0.007(2)
C5 0.064(3) 0.052(3) 0.050(3) 0.006(2) 0.013(2) 0.016(2)
C16 0.046(2) 0.052(3) 0.060(3) -0.006(2) 0.016(2) 0.009(2)
C9 0.052(3) 0.053(3) 0.061(3) -0.014(2) 0.017(2) 0.004(2)
C2 0.056(3) 0.060(3) 0.056(3) 0.011(2) 0.010(2) 0.013(2)
C20 0.062(3) 0.055(3) 0.053(3) 0.004(2) 0.022(2) 0.015(2)
C14 0.069(3) 0.080(4) 0.046(3) 0.005(3) 0.010(3) 0.018(3)
C12 0.068(3) 0.068(3) 0.073(4) 0.019(3) 0.029(3) 0.018(3)
C3 0.051(3) 0.066(3) 0.060(3) -0.012(3) 0.003(2) 0.003(2)
C15 0.057(3) 0.076(4) 0.057(3) -0.014(3) 0.001(2) 0.007(3)
C7 0.079(4) 0.077(4) 0.040(3) -0.003(3) 0.009(3) 0.012(3)
C8 0.070(3) 0.082(4) 0.052(3) -0.014(3) 0.010(3) 0.003(3)
C17 0.056(3) 0.054(3) 0.091(4) -0.015(3) 0.019(3) 0.001(2)
C19 0.076(4) 0.064(3) 0.068(3) 0.019(3) 0.032(3) 0.019(3)
C10 0.060(3) 0.061(3) 0.087(4) -0.019(3) 0.023(3) -0.004(3)
C18 0.073(4) 0.049(3) 0.099(5) 0.010(3) 0.038(3) 0.012(3)
C11 0.070(3) 0.060(3) 0.098(5) 0.007(3) 0.039(3) 0.005(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 C1 2.074(5) . ?
I2 C4 2.077(5) . ?
F4 C6 1.338(5) . ?
F3 C5 1.343(5) . ?
F1 C2 1.348(6) . ?
F2 C3 1.337(6) . ?
C21 C22 1.417(6) . ?
C21 C16 1.422(6) . ?
C21 C20 1.424(6) . ?
C22 C13 1.419(6) . ?
C22 C9 1.420(6) . ?
C1 C6 1.374(7) . ?
C1 C2 1.380(7) . ?
C13 C14 1.429(7) . ?
C13 C12 1.401(7) . ?
C6 C5 1.367(7) . ?
C4 C5 1.368(7) . ?
C4 C3 1.374(7) . ?
C16 C15 1.425(7) . ?
C16 C17 1.396(7) . ?
C9 C8 1.423(7) . ?
C9 C10 1.402(7) . ?
C2 C3 1.368(7) . ?
C20 C7 1.429(7) . ?
C20 C19 1.383(7) . ?
C14 H14 0.9300 . ?
C14 C15 1.330(8) . ?
C12 H12 0.9300 . ?
C12 C11 1.377(8) . ?
C15 H15 0.9300 . ?
C7 H7 0.9300 . ?
C7 C8 1.343(8) . ?
C8 H8 0.9300 . ?
C17 H17 0.9300 . ?
C17 C18 1.370(8) . ?
C19 H19 0.9300 . ?
C19 C18 1.380(8) . ?
C10 H10 0.9300 . ?
C10 C11 1.367(8) . ?
C18 H18 0.9300 . ?
C11 H11 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C22 C21 C16 119.9(4) . . ?
C22 C21 C20 120.5(4) . . ?
C16 C21 C20 119.7(4) . . ?
C21 C22 C13 119.9(4) . . ?
C21 C22 C9 120.2(4) . . ?
C13 C22 C9 119.9(4) . . ?
C6 C1 I1 121.9(4) . . ?
C6 C1 C2 116.8(4) . . ?
C2 C1 I1 121.3(4) . . ?
C22 C13 C14 118.2(4) . . ?
C12 C13 C22 119.3(5) . . ?
C12 C13 C14 122.5(5) . . ?
F4 C6 C1 120.0(4) . . ?
F4 C6 C5 118.7(4) . . ?
C5 C6 C1 121.3(4) . . ?
C5 C4 I2 121.9(4) . . ?
C5 C4 C3 117.6(4) . . ?
C3 C4 I2 120.6(4) . . ?
F3 C5 C6 118.4(4) . . ?
F3 C5 C4 119.9(5) . . ?
C6 C5 C4 121.7(4) . . ?
C21 C16 C15 118.5(5) . . ?
C17 C16 C21 118.6(5) . . ?
C17 C16 C15 122.9(5) . . ?
C22 C9 C8 118.0(5) . . ?
C10 C9 C22 118.1(5) . . ?
C10 C9 C8 123.8(5) . . ?
F1 C2 C1 119.3(5) . . ?
F1 C2 C3 118.8(5) . . ?
C3 C2 C1 121.8(5) . . ?
C21 C20 C7 117.4(5) . . ?
C19 C20 C21 118.8(5) . . ?
C19 C20 C7 123.8(5) . . ?
C13 C14 H14 119.0 . . ?
C15 C14 C13 122.0(5) . . ?
C15 C14 H14 119.0 . . ?
C13 C12 H12 120.0 . . ?
C11 C12 C13 120.0(5) . . ?
C11 C12 H12 120.0 . . ?
F2 C3 C4 120.7(5) . . ?
F2 C3 C2 118.5(5) . . ?
C2 C3 C4 120.8(5) . . ?
C16 C15 H15 119.2 . . ?
C14 C15 C16 121.6(5) . . ?
C14 C15 H15 119.2 . . ?
C20 C7 H7 118.9 . . ?
C8 C7 C20 122.2(5) . . ?
C8 C7 H7 118.9 . . ?
C9 C8 H8 119.1 . . ?
C7 C8 C9 121.7(5) . . ?
C7 C8 H8 119.1 . . ?
C16 C17 H17 119.5 . . ?
C18 C17 C16 121.0(5) . . ?
C18 C17 H17 119.5 . . ?
C20 C19 H19 119.4 . . ?
C18 C19 C20 121.1(5) . . ?
C18 C19 H19 119.4 . . ?
C9 C10 H10 119.3 . . ?
C11 C10 C9 121.3(5) . . ?
C11 C10 H10 119.3 . . ?
C17 C18 C19 120.8(5) . . ?
C17 C18 H18 119.6 . . ?
C19 C18 H18 119.6 . . ?
C12 C11 H11 119.3 . . ?
C10 C11 C12 121.4(5) . . ?
C10 C11 H11 119.3 . . ?

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 C1 C6 F4 0.6(6) . . . . ?
I1 C1 C6 C5 -179.5(4) . . . . ?
I1 C1 C2 F1 -1.1(6) . . . . ?
I1 C1 C2 C3 179.6(4) . . . . ?
I2 C4 C5 F3 1.3(6) . . . . ?
I2 C4 C5 C6 -178.2(4) . . . . ?
I2 C4 C3 F2 -1.0(6) . . . . ?
I2 C4 C3 C2 178.3(4) . . . . ?
F4 C6 C5 F3 0.2(7) . . . . ?
F4 C6 C5 C4 179.7(4) . . . . ?
F1 C2 C3 F2 0.1(7) . . . . ?
F1 C2 C3 C4 -179.3(4) . . . . ?
C21 C22 C13 C14 -1.0(6) . . . . ?
C21 C22 C13 C12 179.0(4) . . . . ?
C21 C22 C9 C8 -0.2(6) . . . . ?
C21 C22 C9 C10 -179.9(4) . . . . ?
C21 C16 C15 C14 -0.6(7) . . . . ?
C21 C16 C17 C18 -1.0(7) . . . . ?
C21 C20 C7 C8 -0.3(7) . . . . ?
C21 C20 C19 C18 0.0(7) . . . . ?
C22 C21 C16 C15 0.6(6) . . . . ?
C22 C21 C16 C17 -178.8(4) . . . . ?
C22 C21 C20 C7 0.7(6) . . . . ?
C22 C21 C20 C19 179.3(4) . . . . ?
C22 C13 C14 C15 1.0(7) . . . . ?
C22 C13 C12 C11 0.5(7) . . . . ?
C22 C9 C8 C7 0.6(7) . . . . ?
C22 C9 C10 C11 1.3(7) . . . . ?
C1 C6 C5 F3 -179.7(4) . . . . ?
C1 C6 C5 C4 -0.2(7) . . . . ?
C1 C2 C3 F2 179.4(4) . . . . ?
C1 C2 C3 C4 0.0(8) . . . . ?
C13 C22 C9 C8 178.8(4) . . . . ?
C13 C22 C9 C10 -0.8(6) . . . . ?
C13 C14 C15 C16 -0.2(8) . . . . ?
C13 C12 C11 C10 -0.1(8) . . . . ?
C6 C1 C2 F1 179.4(4) . . . . ?
C6 C1 C2 C3 0.1(7) . . . . ?
C5 C4 C3 F2 -179.5(4) . . . . ?
C5 C4 C3 C2 -0.2(7) . . . . ?
C16 C21 C22 C13 0.2(6) . . . . ?
C16 C21 C22 C9 179.2(4) . . . . ?
C16 C21 C20 C7 -179.0(4) . . . . ?
C16 C21 C20 C19 -0.4(6) . . . . ?
C16 C17 C18 C19 0.6(8) . . . . ?
C9 C22 C13 C14 179.9(4) . . . . ?
C9 C22 C13 C12 -0.1(6) . . . . ?
C9 C10 C11 C12 -0.8(8) . . . . ?
C2 C1 C6 F4 -179.9(4) . . . . ?
C2 C1 C6 C5 0.0(7) . . . . ?
C20 C21 C22 C13 -179.5(4) . . . . ?
C20 C21 C22 C9 -0.4(6) . . . . ?
C20 C21 C16 C15 -179.7(4) . . . . ?
C20 C21 C16 C17 0.9(6) . . . . ?
C20 C7 C8 C9 -0.3(8) . . . . ?
C20 C19 C18 C17 -0.1(8) . . . . ?
C14 C13 C12 C11 -179.5(5) . . . . ?
C12 C13 C14 C15 -179.0(5) . . . . ?
C3 C4 C5 F3 179.7(4) . . . . ?
C3 C4 C5 C6 0.3(7) . . . . ?
C15 C16 C17 C18 179.6(5) . . . . ?
C7 C20 C19 C18 178.5(5) . . . . ?
C8 C9 C10 C11 -178.3(5) . . . . ?
C17 C16 C15 C14 178.8(5) . . . . ?
C19 C20 C7 C8 -178.9(5) . . . . ?
C10 C9 C8 C7 -179.8(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
