# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_jus1803
_database_code_depnum_ccdc_archive 'CCDC 1982244'
loop_
_audit_author_name
_audit_author_address
'Michael Ferguson'
;University of Alberta
Canada
;
_audit_update_record             
;
2020-02-05 deposited with the CCDC.	2020-04-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        
;
5-chloro-2-iodo-1,3-bis{[4-trifluoromethyl)phenyl]ethynyl}benzene
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H10 Cl F6 I'
_chemical_formula_sum            'C24 H10 Cl F6 I'
_chemical_formula_weight         574.67

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'
Cl Cl 0.1484 0.1585 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.8013(12)
_cell_length_b                   10.0715(12)
_cell_length_c                   11.7314(14)
_cell_angle_alpha                91.3034(15)
_cell_angle_beta                 91.6389(14)
_cell_angle_gamma                111.5614(14)
_cell_volume                     1075.9(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    4048
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      26.27

_exptl_crystal_description       fragment
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.774
_exptl_crystal_F_000             556
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.241
_exptl_crystal_size_mid          0.122
_exptl_crystal_size_min          0.103
_exptl_absorpt_coefficient_mu    1.673
_shelx_estimated_absorpt_T_min   0.689
_shelx_estimated_absorpt_T_max   0.847
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.7647
_exptl_absorpt_correction_T_max  0.9260
_exptl_absorpt_process_details   SADABS-2016/2
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      193(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8291
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_av_R_equivalents  0.0189
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.738
_diffrn_reflns_theta_max         26.590
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4456
_reflns_number_gt                3710
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0510P)²+0.8785P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4456
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0356
_refine_ls_wR_factor_ref         0.1027
_refine_ls_wR_factor_gt          0.0967
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.33158(3) 0.65115(3) 0.25399(2) 0.05633(12) Uani 1 1 d . . . . .
Cl1 Cl -0.05318(11) 1.06507(11) 0.22057(9) 0.0539(2) Uani 1 1 d . . . . .
F1 F 0.5486(3) 0.6717(3) 0.9926(2) 0.0763(8) Uani 1 1 d . . . . .
F2 F 0.7593(3) 0.7694(3) 0.9250(2) 0.0725(8) Uani 1 1 d . . . . .
F3 F 0.6677(4) 0.8953(3) 1.0176(2) 0.0873(9) Uani 1 1 d . . . . .
F4 F 0.3254(3) 0.4116(3) -0.4972(2) 0.0807(9) Uani 1 1 d . . . . .
F5 F 0.0952(4) 0.2966(4) -0.5169(2) 0.0882(10) Uani 1 1 d . . . . .
F6 F 0.2262(4) 0.2104(3) -0.4207(2) 0.0779(8) Uani 1 1 d . . . . .
C1 C 0.2036(3) 0.8656(3) 0.3393(2) 0.0307(6) Uani 1 1 d . . . . .
C2 C 0.2122(3) 0.7838(3) 0.2430(3) 0.0312(6) Uani 1 1 d . . . . .
C3 C 0.1407(3) 0.7911(3) 0.1396(3) 0.0305(6) Uani 1 1 d . . . . .
C4 C 0.0584(4) 0.8793(3) 0.1342(3) 0.0343(7) Uani 1 1 d . . . . .
H4 H 0.007930 0.884074 0.065037 0.041 Uiso 1 1 calc R U . . .
C5 C 0.0509(3) 0.9585(3) 0.2289(3) 0.0344(7) Uani 1 1 d . . . . .
C6 C 0.1221(4) 0.9533(3) 0.3312(3) 0.0342(7) Uani 1 1 d . . . . .
H6 H 0.115507 1.009177 0.395615 0.041 Uiso 1 1 calc R U . . .
C7 C 0.2776(4) 0.8607(4) 0.4458(3) 0.0362(7) Uani 1 1 d . . . . .
C8 C 0.3399(4) 0.8579(4) 0.5336(3) 0.0375(7) Uani 1 1 d . . . . .
C9 C 0.1482(4) 0.7110(3) 0.0388(3) 0.0353(7) Uani 1 1 d . . . . .
C10 C 0.1524(4) 0.6458(4) -0.0463(3) 0.0362(7) Uani 1 1 d . . . . .
C11 C 0.4184(3) 0.8468(3) 0.6363(3) 0.0326(7) Uani 1 1 d . . . . .
C12 C 0.4207(4) 0.9265(4) 0.7354(3) 0.0374(7) Uani 1 1 d . . . . .
H12 H 0.372872 0.993197 0.735534 0.045 Uiso 1 1 calc R U . . .
C13 C 0.4924(4) 0.9085(4) 0.8334(3) 0.0396(8) Uani 1 1 d . . . . .
H13 H 0.493120 0.962492 0.901033 0.048 Uiso 1 1 calc R U . . .
C14 C 0.5628(4) 0.8131(4) 0.8339(3) 0.0355(7) Uani 1 1 d . . . . .
C15 C 0.5640(4) 0.7352(4) 0.7357(3) 0.0423(8) Uani 1 1 d . . . . .
H15 H 0.614870 0.670985 0.735828 0.051 Uiso 1 1 calc R U . . .
C16 C 0.4911(4) 0.7508(4) 0.6370(3) 0.0400(8) Uani 1 1 d . . . . .
H16 H 0.490584 0.696131 0.569793 0.048 Uiso 1 1 calc R U . . .
C17 C 0.6337(4) 0.7873(4) 0.9416(3) 0.0482(9) Uani 1 1 d . . . . .
C21 C 0.1617(3) 0.5636(3) -0.1454(3) 0.0319(7) Uani 1 1 d . . . . .
C22 C 0.1010(4) 0.5789(4) -0.2505(3) 0.0416(8) Uani 1 1 d . . . . .
H22 H 0.050579 0.642960 -0.257173 0.050 Uiso 1 1 calc R U . . .
C23 C 0.1140(4) 0.5010(4) -0.3453(3) 0.0448(9) Uani 1 1 d . . . . .
H23 H 0.072076 0.511694 -0.416921 0.054 Uiso 1 1 calc R U . . .
C24 C 0.1870(4) 0.4081(4) -0.3368(3) 0.0368(7) Uani 1 1 d . . . . .
C25 C 0.2470(4) 0.3908(4) -0.2331(3) 0.0416(8) Uani 1 1 d . . . . .
H25 H 0.296429 0.325840 -0.226874 0.050 Uiso 1 1 calc R U . . .
C26 C 0.2345(4) 0.4694(4) -0.1375(3) 0.0394(8) Uani 1 1 d . . . . .
H26 H 0.276421 0.458271 -0.066027 0.047 Uiso 1 1 calc R U . . .
C27 C 0.2082(5) 0.3316(4) -0.4419(3) 0.0514(10) 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 C2 2.078(3) . ?
Cl1 C5 1.734(3) . ?
F1 C17 1.325(5) . ?
F2 C17 1.327(5) . ?
F3 C17 1.327(5) . ?
F4 C27 1.332(5) . ?
F5 C27 1.330(5) . ?
F6 C27 1.323(5) . ?
C1 C6 1.395(5) . ?
C1 C2 1.406(4) . ?
C1 C7 1.437(4) . ?
C2 C3 1.400(4) . ?
C3 C4 1.403(4) . ?
C3 C9 1.435(4) . ?
C4 C5 1.372(4) . ?
C5 C6 1.383(5) . ?
C7 C8 1.189(5) . ?
C8 C11 1.439(4) . ?
C9 C10 1.193(4) . ?
C10 C21 1.436(4) . ?
C11 C12 1.392(4) . ?
C11 C16 1.396(5) . ?
C12 C13 1.381(5) . ?
C13 C14 1.373(5) . ?
C14 C15 1.382(5) . ?
C14 C17 1.499(5) . ?
C15 C16 1.385(5) . ?
C21 C26 1.383(5) . ?
C21 C22 1.390(5) . ?
C22 C23 1.382(5) . ?
C23 C24 1.375(5) . ?
C24 C25 1.379(5) . ?
C24 C27 1.499(5) . ?
C25 C26 1.392(5) . ?

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 119.3(3) . . ?
C6 C1 C7 119.5(3) . . ?
C2 C1 C7 121.2(3) . . ?
C3 C2 C1 120.4(3) . . ?
C3 C2 I1 119.8(2) . . ?
C1 C2 I1 119.9(2) . . ?
C2 C3 C4 119.0(3) . . ?
C2 C3 C9 122.3(3) . . ?
C4 C3 C9 118.7(3) . . ?
C5 C4 C3 120.0(3) . . ?
C4 C5 C6 121.6(3) . . ?
C4 C5 Cl1 119.2(2) . . ?
C6 C5 Cl1 119.3(2) . . ?
C5 C6 C1 119.7(3) . . ?
C8 C7 C1 179.3(4) . . ?
C7 C8 C11 175.9(4) . . ?
C10 C9 C3 178.5(4) . . ?
C9 C10 C21 177.0(4) . . ?
C12 C11 C16 119.3(3) . . ?
C12 C11 C8 121.8(3) . . ?
C16 C11 C8 118.9(3) . . ?
C13 C12 C11 120.0(3) . . ?
C14 C13 C12 120.5(3) . . ?
C13 C14 C15 120.3(3) . . ?
C13 C14 C17 120.7(3) . . ?
C15 C14 C17 119.0(3) . . ?
C14 C15 C16 119.9(3) . . ?
C15 C16 C11 120.0(3) . . ?
F1 C17 F2 106.2(3) . . ?
F1 C17 F3 106.8(3) . . ?
F2 C17 F3 104.9(3) . . ?
F1 C17 C14 112.2(3) . . ?
F2 C17 C14 113.2(3) . . ?
F3 C17 C14 112.9(3) . . ?
C26 C21 C22 119.0(3) . . ?
C26 C21 C10 119.9(3) . . ?
C22 C21 C10 121.1(3) . . ?
C23 C22 C21 120.1(3) . . ?
C24 C23 C22 120.5(3) . . ?
C23 C24 C25 120.1(3) . . ?
C23 C24 C27 119.7(3) . . ?
C25 C24 C27 120.1(3) . . ?
C24 C25 C26 119.5(3) . . ?
C21 C26 C25 120.7(3) . . ?
F6 C27 F5 105.5(3) . . ?
F6 C27 F4 106.7(3) . . ?
F5 C27 F4 106.1(4) . . ?
F6 C27 C24 113.4(3) . . ?
F5 C27 C24 113.0(3) . . ?
F4 C27 C24 111.6(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
C6 C1 C2 C3 0.5(5) . . . . ?
C7 C1 C2 C3 -179.3(3) . . . . ?
C6 C1 C2 I1 -179.5(2) . . . . ?
C7 C1 C2 I1 0.7(4) . . . . ?
C1 C2 C3 C4 -1.1(5) . . . . ?
I1 C2 C3 C4 178.9(2) . . . . ?
C1 C2 C3 C9 179.1(3) . . . . ?
I1 C2 C3 C9 -0.9(4) . . . . ?
C2 C3 C4 C5 1.1(5) . . . . ?
C9 C3 C4 C5 -179.1(3) . . . . ?
C3 C4 C5 C6 -0.5(5) . . . . ?
C3 C4 C5 Cl1 -179.2(3) . . . . ?
C4 C5 C6 C1 -0.1(5) . . . . ?
Cl1 C5 C6 C1 178.7(2) . . . . ?
C2 C1 C6 C5 0.1(5) . . . . ?
C7 C1 C6 C5 179.9(3) . . . . ?
C16 C11 C12 C13 -1.0(5) . . . . ?
C8 C11 C12 C13 177.4(3) . . . . ?
C11 C12 C13 C14 0.5(5) . . . . ?
C12 C13 C14 C15 0.8(5) . . . . ?
C12 C13 C14 C17 -176.6(3) . . . . ?
C13 C14 C15 C16 -1.5(5) . . . . ?
C17 C14 C15 C16 175.9(3) . . . . ?
C14 C15 C16 C11 1.0(5) . . . . ?
C12 C11 C16 C15 0.2(5) . . . . ?
C8 C11 C16 C15 -178.2(3) . . . . ?
C13 C14 C17 F1 97.8(4) . . . . ?
C15 C14 C17 F1 -79.7(5) . . . . ?
C13 C14 C17 F2 -142.0(4) . . . . ?
C15 C14 C17 F2 40.6(5) . . . . ?
C13 C14 C17 F3 -23.0(5) . . . . ?
C15 C14 C17 F3 159.5(4) . . . . ?
C26 C21 C22 C23 -0.1(5) . . . . ?
C10 C21 C22 C23 178.6(3) . . . . ?
C21 C22 C23 C24 -0.1(6) . . . . ?
C22 C23 C24 C25 0.6(6) . . . . ?
C22 C23 C24 C27 -176.1(4) . . . . ?
C23 C24 C25 C26 -0.8(5) . . . . ?
C27 C24 C25 C26 175.9(3) . . . . ?
C22 C21 C26 C25 0.0(5) . . . . ?
C10 C21 C26 C25 -178.8(3) . . . . ?
C24 C25 C26 C21 0.5(5) . . . . ?
C23 C24 C27 F6 -155.4(4) . . . . ?
C25 C24 C27 F6 27.9(5) . . . . ?
C23 C24 C27 F5 -35.4(5) . . . . ?
C25 C24 C27 F5 147.9(4) . . . . ?
C23 C24 C27 F4 84.0(5) . . . . ?
C25 C24 C27 F4 -92.7(4) . . . . ?

_refine_diff_density_max         0.504
_refine_diff_density_min         -0.518
_refine_diff_density_rms         0.077


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane'
####################################################################### 
# 
# 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_jus1808
_database_code_depnum_ccdc_archive 'CCDC 1982245'
loop_
_audit_author_name
_audit_author_address
'Michael Ferguson'
;University of Alberta
Canada
;
_audit_update_record             
;
2020-02-05 deposited with the CCDC.	2020-04-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        
;
1,2-diiodo-3-{[4-(trifluoromethyl)phenyl]ethynyl}benzene
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H7 F3 I2'
_chemical_formula_sum            'C15 H7 F3 I2'
_chemical_formula_weight         498.01

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 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   12.1687(8)
_cell_length_b                   4.3193(3)
_cell_length_c                   27.7962(17)
_cell_angle_alpha                90
_cell_angle_beta                 90.1567(9)
_cell_angle_gamma                90
_cell_volume                     1460.97(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9886
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      30.51

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.264
_exptl_crystal_F_000             920
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.185
_exptl_crystal_size_mid          0.183
_exptl_crystal_size_min          0.119
_exptl_absorpt_coefficient_mu    4.324
_shelx_estimated_absorpt_T_min   0.502
_shelx_estimated_absorpt_T_max   0.627
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.2634
_exptl_absorpt_correction_T_max  0.3623
_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_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16567
_diffrn_reflns_av_unetI/netI     0.0138
_diffrn_reflns_av_R_equivalents  0.0171
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_theta_min         1.465
_diffrn_reflns_theta_max         30.530
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4473
_reflns_number_gt                4127
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2014 (Sheldrick 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0241P)²+1.1974P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4473
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0281
_refine_ls_R_factor_gt           0.0250
_refine_ls_wR_factor_ref         0.0575
_refine_ls_wR_factor_gt          0.0563
_refine_ls_goodness_of_fit_ref   1.161
_refine_ls_restrained_S_all      1.161
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.57436(2) 0.08974(4) 0.92983(2) 0.03552(5) Uani 1 1 d . . . . .
I2 I 0.47038(2) 0.04206(4) 0.80711(2) 0.03373(5) Uani 1 1 d . . . . .
F1A F -0.0176(7) 0.5282(19) 0.5557(3) 0.063(2) Uani 0.502(10) 1 d . . P A 1
F2A F 0.1456(7) 0.381(2) 0.5361(3) 0.061(2) Uani 0.502(10) 1 d . . P A 1
F3A F 0.0208(6) 0.0502(14) 0.55431(17) 0.069(2) Uani 0.502(10) 1 d . . P A 1
F1B F -0.0044(7) 0.367(3) 0.5521(3) 0.082(4) Uani 0.498(10) 1 d . . P A 2
F2B F 0.1590(7) 0.523(2) 0.5416(3) 0.0587(19) Uani 0.498(10) 1 d . . P A 2
F3B F 0.1261(10) 0.0419(14) 0.54445(18) 0.105(4) Uani 0.498(10) 1 d . . P A 2
C1 C 0.42064(19) 0.2673(5) 0.90982(8) 0.0272(4) Uani 1 1 d . . . . .
C2 C 0.38129(19) 0.2496(5) 0.86277(8) 0.0264(4) Uani 1 1 d . . . . .
C3 C 0.2778(2) 0.3791(6) 0.85183(9) 0.0304(5) Uani 1 1 d . . . . .
C4 C 0.2176(2) 0.5249(7) 0.88824(10) 0.0377(6) Uani 1 1 d . . . . .
H4 H 0.148358 0.615176 0.880922 0.045 Uiso 1 1 calc R U . . .
C5 C 0.2580(2) 0.5385(7) 0.93474(10) 0.0407(6) Uani 1 1 d . . . . .
H5 H 0.216279 0.636256 0.959251 0.049 Uiso 1 1 calc R U . . .
C6 C 0.3593(2) 0.4096(6) 0.94558(9) 0.0350(5) Uani 1 1 d . . . . .
H6 H 0.386839 0.418613 0.977558 0.042 Uiso 1 1 calc R U . . .
C7 C 0.2338(2) 0.3693(7) 0.80382(10) 0.0357(5) Uani 1 1 d . . . . .
C8 C 0.1986(2) 0.3626(7) 0.76386(10) 0.0358(5) Uani 1 1 d . . . . .
C9 C 0.1649(2) 0.3476(6) 0.71426(9) 0.0319(5) Uani 1 1 d . . . . .
C10 C 0.2283(2) 0.1774(7) 0.68185(10) 0.0391(6) Uani 1 1 d . . . . .
H10 H 0.291283 0.067694 0.692721 0.047 Uiso 1 1 calc R U . . .
C11 C 0.1984(3) 0.1700(7) 0.63341(11) 0.0447(7) Uani 1 1 d . . . . .
H11 H 0.241337 0.055183 0.611187 0.054 Uiso 1 1 calc R U . . .
C12 C 0.1068(3) 0.3282(7) 0.61760(9) 0.0411(6) Uani 1 1 d . . . . .
C13 C 0.0424(2) 0.4936(7) 0.64961(10) 0.0397(6) Uani 1 1 d . . . . .
H13 H -0.021146 0.600429 0.638620 0.048 Uiso 1 1 calc R U . . .
C14 C 0.0715(2) 0.5014(7) 0.69783(10) 0.0359(5) Uani 1 1 d . . . . .
H14 H 0.027300 0.613203 0.719944 0.043 Uiso 1 1 calc R U . . .
C15A C 0.0590(9) 0.329(4) 0.5657(6) 0.042(2) Uani 0.502(10) 1 d . . P A 1
C15B C 0.0989(12) 0.316(4) 0.5639(5) 0.047(3) Uani 0.498(10) 1 d . . 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 C1 2.096(2) . ?
I2 C2 2.093(2) . ?
F1A C15A 1.299(15) . ?
F2A C15A 1.357(12) . ?
F3A C15A 1.328(17) . ?
F1B C15B 1.317(14) . ?
F2B C15B 1.311(15) . ?
F3B C15B 1.344(18) . ?
C1 C6 1.388(3) . ?
C1 C2 1.394(3) . ?
C2 C3 1.410(3) . ?
C3 C4 1.401(4) . ?
C3 C7 1.437(4) . ?
C4 C5 1.383(4) . ?
C5 C6 1.385(4) . ?
C7 C8 1.190(4) . ?
C8 C9 1.439(4) . ?
C9 C10 1.397(4) . ?
C9 C14 1.392(4) . ?
C10 C11 1.394(4) . ?
C11 C12 1.378(5) . ?
C12 C13 1.386(4) . ?
C12 C15B 1.497(15) . ?
C12 C15A 1.554(16) . ?
C13 C14 1.386(4) . ?

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 120.8(2) . . ?
C6 C1 I1 116.97(18) . . ?
C2 C1 I1 122.21(17) . . ?
C1 C2 C3 119.0(2) . . ?
C1 C2 I2 122.68(17) . . ?
C3 C2 I2 118.32(17) . . ?
C4 C3 C2 119.4(2) . . ?
C4 C3 C7 119.3(2) . . ?
C2 C3 C7 121.3(2) . . ?
C5 C4 C3 120.6(2) . . ?
C4 C5 C6 120.0(2) . . ?
C5 C6 C1 120.2(2) . . ?
C8 C7 C3 179.2(3) . . ?
C7 C8 C9 175.3(3) . . ?
C10 C9 C14 119.4(2) . . ?
C10 C9 C8 119.0(2) . . ?
C14 C9 C8 121.5(2) . . ?
C9 C10 C11 119.5(3) . . ?
C10 C11 C12 120.3(3) . . ?
C11 C12 C13 120.6(3) . . ?
C11 C12 C15B 110.5(7) . . ?
C13 C12 C15B 128.6(7) . . ?
C11 C12 C15A 126.6(6) . . ?
C13 C12 C15A 112.6(6) . . ?
C14 C13 C12 119.3(3) . . ?
C13 C14 C9 120.8(3) . . ?
F1A C15A F3A 107.4(10) . . ?
F1A C15A F2A 108.6(13) . . ?
F3A C15A F2A 106.2(11) . . ?
F1A C15A C12 117.8(11) . . ?
F3A C15A C12 110.5(11) . . ?
F2A C15A C12 105.8(8) . . ?
F2B C15B F1B 107.6(14) . . ?
F2B C15B F3B 105.8(10) . . ?
F1B C15B F3B 106.6(13) . . ?
F2B C15B C12 114.3(11) . . ?
F1B C15B C12 107.5(9) . . ?
F3B C15B C12 114.6(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
C6 C1 C2 C3 0.1(4) . . . . ?
I1 C1 C2 C3 -178.90(17) . . . . ?
C6 C1 C2 I2 179.39(19) . . . . ?
I1 C1 C2 I2 0.4(3) . . . . ?
C1 C2 C3 C4 0.6(4) . . . . ?
I2 C2 C3 C4 -178.7(2) . . . . ?
C1 C2 C3 C7 179.5(2) . . . . ?
I2 C2 C3 C7 0.2(3) . . . . ?
C2 C3 C4 C5 -0.9(4) . . . . ?
C7 C3 C4 C5 -179.9(3) . . . . ?
C3 C4 C5 C6 0.5(5) . . . . ?
C4 C5 C6 C1 0.2(5) . . . . ?
C2 C1 C6 C5 -0.5(4) . . . . ?
I1 C1 C6 C5 178.5(2) . . . . ?
C14 C9 C10 C11 1.4(4) . . . . ?
C8 C9 C10 C11 -177.9(3) . . . . ?
C9 C10 C11 C12 -0.2(4) . . . . ?
C10 C11 C12 C13 -0.8(4) . . . . ?
C10 C11 C12 C15B 173.5(7) . . . . ?
C10 C11 C12 C15A -176.4(8) . . . . ?
C11 C12 C13 C14 0.7(4) . . . . ?
C15B C12 C13 C14 -172.5(8) . . . . ?
C15A C12 C13 C14 176.9(7) . . . . ?
C12 C13 C14 C9 0.5(4) . . . . ?
C10 C9 C14 C13 -1.5(4) . . . . ?
C8 C9 C14 C13 177.7(3) . . . . ?
C11 C12 C15A F1A -169.6(8) . . . . ?
C13 C12 C15A F1A 14.5(14) . . . . ?
C11 C12 C15A F3A 66.5(10) . . . . ?
C13 C12 C15A F3A -109.4(8) . . . . ?
C11 C12 C15A F2A -48.1(14) . . . . ?
C13 C12 C15A F2A 136.1(9) . . . . ?
C11 C12 C15B F2B -82.7(14) . . . . ?
C13 C12 C15B F2B 91.0(13) . . . . ?
C11 C12 C15B F1B 157.9(10) . . . . ?
C13 C12 C15B F1B -28.3(16) . . . . ?
C11 C12 C15B F3B 39.7(11) . . . . ?
C13 C12 C15B F3B -146.6(8) . . . . ?

_refine_diff_density_max         1.059
_refine_diff_density_min         -0.795
_refine_diff_density_rms         0.094


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexanes/dichloromethane'
####################################################################### 
# 
# 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_jus1810
_database_code_depnum_ccdc_archive 'CCDC 1982247'
loop_
_audit_author_name
_audit_author_address
'Michael Ferguson'
;University of Alberta
Canada
;
_audit_update_record             
;
2020-02-05 deposited with the CCDC.	2020-04-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        
;
5-chloro-1,2-diiodo-3-{[4-(trifluoromethyl)phenyl]ethynyl}benzene
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H6 Cl F3 I2'
_chemical_formula_sum            'C15 H6 Cl F3 I2'
_chemical_formula_weight         532.45

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'
Cl Cl 0.1484 0.1585 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.4281(5)
_cell_length_b                   9.5746(5)
_cell_length_c                   11.4227(6)
_cell_angle_alpha                72.6614(8)
_cell_angle_beta                 71.6046(7)
_cell_angle_gamma                64.6041(7)
_cell_volume                     775.78(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9944
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      30.57

_exptl_crystal_description       fragment
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.279
_exptl_crystal_F_000             492
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.215
_exptl_crystal_size_mid          0.181
_exptl_crystal_size_min          0.071
_exptl_absorpt_coefficient_mu    4.246
_shelx_estimated_absorpt_T_min   0.462
_shelx_estimated_absorpt_T_max   0.753
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.3060
_exptl_absorpt_correction_T_max  0.4694
_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_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9508
_diffrn_reflns_av_unetI/netI     0.0133
_diffrn_reflns_av_R_equivalents  0.0091
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.914
_diffrn_reflns_theta_max         30.631
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4763
_reflns_number_gt                4325
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0165P)²+0.6203P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4763
_refine_ls_number_parameters     203
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0207
_refine_ls_R_factor_gt           0.0180
_refine_ls_wR_factor_ref         0.0426
_refine_ls_wR_factor_gt          0.0414
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.44908(2) 0.08527(2) 0.14714(2) 0.03707(4) Uani 1 1 d . . . . .
I2 I 0.25724(2) 0.37122(2) 0.35374(2) 0.03377(4) Uani 1 1 d . . . . .
Cl1 Cl 1.05747(6) -0.19302(6) 0.36331(5) 0.03706(11) Uani 1 1 d . . . . .
F1A F 0.1791(3) 0.7698(3) 1.0301(2) 0.0708(8) Uani 0.912(5) 1 d . . P A 1
F2A F -0.0121(4) 0.6629(3) 1.0946(2) 0.0831(11) Uani 0.912(5) 1 d . . P A 1
F3A F -0.0486(4) 0.8712(2) 0.9507(2) 0.0779(8) Uani 0.912(5) 1 d . . P A 1
F1B F 0.137(3) 0.695(2) 1.0837(19) 0.055(5) Uiso 0.088(5) 1 d . . P A 2
F2B F -0.096(2) 0.7246(18) 1.0398(15) 0.034(4) Uiso 0.088(5) 1 d . . P A 2
F3B F 0.030(2) 0.8685(19) 0.9569(15) 0.032(4) Uiso 0.088(5) 1 d . . P A 2
C1 C 0.5799(2) 0.07908(19) 0.27788(15) 0.0238(3) Uani 1 1 d . . . . .
C2 C 0.5027(2) 0.18285(18) 0.36200(15) 0.0217(3) Uani 1 1 d . . . . .
C3 C 0.5946(2) 0.16239(18) 0.45313(15) 0.0218(3) Uani 1 1 d . . . . .
C4 C 0.7641(2) 0.0427(2) 0.45541(16) 0.0243(3) Uani 1 1 d . . . . .
H4 H 0.825829 0.026761 0.517786 0.029 Uiso 1 1 calc R U . . .
C5 C 0.8414(2) -0.05230(19) 0.36643(16) 0.0245(3) Uani 1 1 d . . . . .
C6 C 0.7502(2) -0.0383(2) 0.27907(16) 0.0260(3) Uani 1 1 d . . . . .
H6 H 0.802955 -0.107557 0.220897 0.031 Uiso 1 1 calc R U . . .
C7 C 0.5171(2) 0.2612(2) 0.54510(16) 0.0249(3) Uani 1 1 d . . . . .
C8 C 0.4514(2) 0.3407(2) 0.62378(16) 0.0253(3) Uani 1 1 d . . . . .
C9 C 0.3587(2) 0.4396(2) 0.71634(16) 0.0240(3) Uani 1 1 d . . . . .
C10 C 0.2050(2) 0.5720(2) 0.69627(16) 0.0272(3) Uani 1 1 d . . . . .
H10 H 0.164151 0.596713 0.621359 0.033 Uiso 1 1 calc R U . . .
C11 C 0.1113(2) 0.6681(2) 0.78531(17) 0.0292(4) Uani 1 1 d . . . . .
H11 H 0.006301 0.758089 0.771689 0.035 Uiso 1 1 calc R U . . .
C12 C 0.1722(3) 0.6318(2) 0.89390(17) 0.0281(3) Uani 1 1 d . . . . .
C13 C 0.3244(3) 0.5000(2) 0.91547(18) 0.0343(4) Uani 1 1 d . . . . .
H13 H 0.364075 0.475653 0.990826 0.041 Uiso 1 1 calc R U . . .
C14 C 0.4185(3) 0.4038(2) 0.82681(18) 0.0320(4) Uani 1 1 d . . . . .
H14 H 0.523292 0.313854 0.841038 0.038 Uiso 1 1 calc R U . . .
C15 C 0.0718(3) 0.7332(3) 0.9918(2) 0.0380(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
I1 C1 2.0930(17) . ?
I2 C2 2.0887(16) . ?
Cl1 C5 1.7368(17) . ?
F1A C15 1.321(3) . ?
F2A C15 1.321(3) . ?
F3A C15 1.334(3) . ?
F1B C15 1.226(19) . ?
F2B C15 1.375(15) . ?
F3B C15 1.163(16) . ?
C1 C6 1.394(2) . ?
C1 C2 1.398(2) . ?
C2 C3 1.407(2) . ?
C3 C4 1.399(2) . ?
C3 C7 1.433(2) . ?
C4 C5 1.382(2) . ?
C5 C6 1.385(2) . ?
C7 C8 1.195(2) . ?
C8 C9 1.437(2) . ?
C9 C10 1.394(2) . ?
C9 C14 1.400(3) . ?
C10 C11 1.390(2) . ?
C11 C12 1.383(3) . ?
C12 C13 1.387(3) . ?
C12 C15 1.502(2) . ?
C13 C14 1.388(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
C6 C1 C2 120.80(15) . . ?
C6 C1 I1 116.08(12) . . ?
C2 C1 I1 123.10(12) . . ?
C1 C2 C3 119.20(15) . . ?
C1 C2 I2 121.91(12) . . ?
C3 C2 I2 118.87(11) . . ?
C4 C3 C2 119.74(14) . . ?
C4 C3 C7 119.03(15) . . ?
C2 C3 C7 121.23(15) . . ?
C5 C4 C3 119.64(16) . . ?
C4 C5 C6 121.50(16) . . ?
C4 C5 Cl1 119.64(13) . . ?
C6 C5 Cl1 118.86(13) . . ?
C5 C6 C1 118.95(15) . . ?
C8 C7 C3 178.48(19) . . ?
C7 C8 C9 175.39(19) . . ?
C10 C9 C14 119.64(15) . . ?
C10 C9 C8 119.25(16) . . ?
C14 C9 C8 121.10(16) . . ?
C11 C10 C9 120.33(17) . . ?
C12 C11 C10 119.49(17) . . ?
C11 C12 C13 120.83(16) . . ?
C11 C12 C15 120.32(18) . . ?
C13 C12 C15 118.83(18) . . ?
C12 C13 C14 119.90(17) . . ?
C13 C14 C9 119.80(17) . . ?
F3B C15 F1B 108.8(12) . . ?
F2A C15 F1A 105.2(2) . . ?
F2A C15 F3A 108.1(2) . . ?
F1A C15 F3A 104.9(2) . . ?
F3B C15 F2B 99.5(10) . . ?
F1B C15 F2B 104.9(12) . . ?
F3B C15 C12 116.9(8) . . ?
F1B C15 C12 116.2(9) . . ?
F2A C15 C12 112.55(17) . . ?
F1A C15 C12 112.51(18) . . ?
F3A C15 C12 113.06(19) . . ?
F2B C15 C12 108.5(6) . . ?

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 -3.5(3) . . . . ?
I1 C1 C2 C3 175.11(12) . . . . ?
C6 C1 C2 I2 175.00(13) . . . . ?
I1 C1 C2 I2 -6.4(2) . . . . ?
C1 C2 C3 C4 2.3(2) . . . . ?
I2 C2 C3 C4 -176.20(12) . . . . ?
C1 C2 C3 C7 -177.05(16) . . . . ?
I2 C2 C3 C7 4.4(2) . . . . ?
C2 C3 C4 C5 1.3(3) . . . . ?
C7 C3 C4 C5 -179.28(16) . . . . ?
C3 C4 C5 C6 -4.0(3) . . . . ?
C3 C4 C5 Cl1 176.10(13) . . . . ?
C4 C5 C6 C1 2.8(3) . . . . ?
Cl1 C5 C6 C1 -177.24(14) . . . . ?
C2 C1 C6 C5 0.9(3) . . . . ?
I1 C1 C6 C5 -177.74(13) . . . . ?
C14 C9 C10 C11 -0.1(3) . . . . ?
C8 C9 C10 C11 178.98(17) . . . . ?
C9 C10 C11 C12 0.3(3) . . . . ?
C10 C11 C12 C13 -0.6(3) . . . . ?
C10 C11 C12 C15 -179.38(18) . . . . ?
C11 C12 C13 C14 0.7(3) . . . . ?
C15 C12 C13 C14 179.47(19) . . . . ?
C12 C13 C14 C9 -0.4(3) . . . . ?
C10 C9 C14 C13 0.1(3) . . . . ?
C8 C9 C14 C13 -178.88(19) . . . . ?
C11 C12 C15 F3B -47.4(10) . . . . ?
C13 C12 C15 F3B 133.8(10) . . . . ?
C11 C12 C15 F1B -178.2(13) . . . . ?
C13 C12 C15 F1B 3.0(13) . . . . ?
C11 C12 C15 F2A 109.0(3) . . . . ?
C13 C12 C15 F2A -69.8(3) . . . . ?
C11 C12 C15 F1A -132.4(2) . . . . ?
C13 C12 C15 F1A 48.8(3) . . . . ?
C11 C12 C15 F3A -13.8(3) . . . . ?
C13 C12 C15 F3A 167.4(2) . . . . ?
C11 C12 C15 F2B 64.0(8) . . . . ?
C13 C12 C15 F2B -114.8(8) . . . . ?

_refine_diff_density_max         1.103
_refine_diff_density_min         -0.604
_refine_diff_density_rms         0.071


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexanes/dichloromethane'
####################################################################### 
# 
# 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_jus1809
_database_code_depnum_ccdc_archive 'CCDC 1982246'
loop_
_audit_author_name
_audit_author_address
'Michael Ferguson'
;University of Alberta
Canada
;
_audit_update_record             
;
2020-02-05 deposited with the CCDC.	2020-04-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        
;
5-fluoro-1,2-diiodo-3-[(4-methoxyphenyl)ethynyl]benzene
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H9 F I2 O'
_chemical_formula_sum            'C15 H9 F I2 O'
_chemical_formula_weight         478.02

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   4.15290(8)
_cell_length_b                   11.4859(2)
_cell_length_c                   30.5943(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1459.35(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9894
_cell_measurement_theta_min      4.11
_cell_measurement_theta_max      73.63

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.176
_exptl_crystal_F_000             888
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.158
_exptl_crystal_size_mid          0.127
_exptl_crystal_size_min          0.028
_exptl_absorpt_coefficient_mu    33.866
_shelx_estimated_absorpt_T_min   0.075
_shelx_estimated_absorpt_T_max   0.451
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.0046
_exptl_absorpt_correction_T_max  0.1121
_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_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9797
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_theta_min         2.889
_diffrn_reflns_theta_max         74.087
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2934
_reflns_number_gt                2918
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.657
_reflns_Friedel_fraction_max     0.995
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Refined as a 2-component inversion twin. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0147P)²+0.2798P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Refined as an inversion twin. 
;
_refine_ls_abs_structure_Flack   0.037(8)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2934
_refine_ls_number_parameters     174
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0150
_refine_ls_R_factor_gt           0.0149
_refine_ls_wR_factor_ref         0.0380
_refine_ls_wR_factor_gt          0.0379
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_restrained_S_all      1.112
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I -0.06974(6) 0.63448(2) 0.52821(2) 0.05149(8) Uani 1 1 d . . . . .
I2 I 0.24743(6) 0.67450(2) 0.63847(2) 0.04729(7) Uani 1 1 d . . . . .
F1 F 0.2990(10) 0.1948(2) 0.54633(8) 0.0723(9) Uani 1 1 d . . . . .
O1 O 1.1160(9) 0.5739(3) 0.87119(9) 0.0561(7) Uani 1 1 d . . . . .
C1 C 0.1469(8) 0.5001(3) 0.56417(11) 0.0401(7) Uani 1 1 d . . . . .
C2 C 0.2755(9) 0.5159(3) 0.60570(10) 0.0385(6) Uani 1 1 d . . . . .
C3 C 0.4262(10) 0.4211(3) 0.62718(10) 0.0394(7) Uani 1 1 d . . . . .
C4 C 0.4359(11) 0.3119(3) 0.60624(11) 0.0470(8) Uani 1 1 d . . . . .
H4 H 0.535828 0.246984 0.619904 0.056 Uiso 1 1 calc R U . . .
C5 C 0.2982(12) 0.3013(3) 0.56583(12) 0.0507(9) Uani 1 1 d . . . . .
C6 C 0.1561(10) 0.3915(4) 0.54378(11) 0.0496(9) Uani 1 1 d . . . . .
H6 H 0.066699 0.380400 0.515506 0.059 Uiso 1 1 calc R U . . .
C7 C 0.5640(10) 0.4345(3) 0.66967(11) 0.0414(7) Uani 1 1 d . . . . .
C8 C 0.6764(9) 0.4488(3) 0.70508(11) 0.0426(8) Uani 1 1 d . . . . .
C9 C 0.7992(9) 0.4771(3) 0.74767(11) 0.0409(7) Uani 1 1 d . . . . .
C10 C 0.9692(10) 0.3973(3) 0.77266(11) 0.0436(8) Uani 1 1 d . . . . .
H10 H 1.009023 0.321629 0.761338 0.052 Uiso 1 1 calc R U . . .
C11 C 1.0819(11) 0.4262(3) 0.81398(11) 0.0429(7) Uani 1 1 d . . . . .
H11 H 1.198483 0.370867 0.830762 0.052 Uiso 1 1 calc R U . . .
C12 C 1.0227(10) 0.5374(3) 0.83070(11) 0.0432(8) Uani 1 1 d . . . . .
C13 C 0.8563(10) 0.6189(3) 0.80560(13) 0.0481(9) Uani 1 1 d . . . . .
H13 H 0.819425 0.694991 0.816703 0.058 Uiso 1 1 calc R U . . .
C14 C 0.7451(12) 0.5889(3) 0.76452(11) 0.0450(7) Uani 1 1 d . . . . .
H14 H 0.630933 0.644532 0.747562 0.054 Uiso 1 1 calc R U . . .
C15 C 1.2571(15) 0.4896(4) 0.89985(13) 0.0617(11) Uani 1 1 d . . . . .
H15A H 1.286659 0.524056 0.928881 0.074 Uiso 1 1 calc R U . . .
H15B H 1.466455 0.465302 0.888212 0.074 Uiso 1 1 calc R U . . .
H15C H 1.114923 0.421781 0.902078 0.074 Uiso 1 1 calc R U . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C1 2.098(3) . ?
I2 C2 2.083(3) . ?
F1 C5 1.361(5) . ?
O1 C12 1.364(4) . ?
O1 C15 1.432(5) . ?
C1 C2 1.390(5) . ?
C1 C6 1.395(6) . ?
C2 C3 1.418(5) . ?
C3 C4 1.409(5) . ?
C3 C7 1.429(5) . ?
C4 C5 1.368(6) . ?
C5 C6 1.370(6) . ?
C7 C8 1.191(5) . ?
C8 C9 1.437(5) . ?
C9 C10 1.387(5) . ?
C9 C14 1.401(5) . ?
C10 C11 1.388(5) . ?
C11 C12 1.397(5) . ?
C12 C13 1.395(6) . ?
C13 C14 1.383(5) . ?

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
C12 O1 C15 117.7(3) . . ?
C2 C1 C6 121.0(3) . . ?
C2 C1 I1 123.2(3) . . ?
C6 C1 I1 115.8(3) . . ?
C1 C2 C3 119.5(3) . . ?
C1 C2 I2 122.2(3) . . ?
C3 C2 I2 118.3(2) . . ?
C4 C3 C2 119.0(3) . . ?
C4 C3 C7 119.9(3) . . ?
C2 C3 C7 121.1(3) . . ?
C5 C4 C3 118.6(4) . . ?
F1 C5 C4 118.4(4) . . ?
F1 C5 C6 117.7(4) . . ?
C4 C5 C6 123.9(4) . . ?
C5 C6 C1 117.9(3) . . ?
C8 C7 C3 178.2(4) . . ?
C7 C8 C9 174.5(4) . . ?
C10 C9 C14 119.0(3) . . ?
C10 C9 C8 122.0(3) . . ?
C14 C9 C8 119.0(3) . . ?
C9 C10 C11 121.0(3) . . ?
C10 C11 C12 119.5(4) . . ?
O1 C12 C13 115.7(3) . . ?
O1 C12 C11 124.3(4) . . ?
C13 C12 C11 119.9(3) . . ?
C14 C13 C12 119.9(4) . . ?
C13 C14 C9 120.6(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
C6 C1 C2 C3 1.8(5) . . . . ?
I1 C1 C2 C3 -178.1(3) . . . . ?
C6 C1 C2 I2 -177.1(3) . . . . ?
I1 C1 C2 I2 3.1(4) . . . . ?
C1 C2 C3 C4 -1.4(6) . . . . ?
I2 C2 C3 C4 177.4(3) . . . . ?
C1 C2 C3 C7 179.3(3) . . . . ?
I2 C2 C3 C7 -1.8(5) . . . . ?
C2 C3 C4 C5 -0.1(6) . . . . ?
C7 C3 C4 C5 179.1(4) . . . . ?
C3 C4 C5 F1 -177.9(4) . . . . ?
C3 C4 C5 C6 1.4(7) . . . . ?
F1 C5 C6 C1 178.3(4) . . . . ?
C4 C5 C6 C1 -1.1(7) . . . . ?
C2 C1 C6 C5 -0.5(6) . . . . ?
I1 C1 C6 C5 179.3(3) . . . . ?
C14 C9 C10 C11 0.7(6) . . . . ?
C8 C9 C10 C11 -179.2(4) . . . . ?
C9 C10 C11 C12 0.2(6) . . . . ?
C15 O1 C12 C13 173.6(4) . . . . ?
C15 O1 C12 C11 -6.0(6) . . . . ?
C10 C11 C12 O1 178.4(4) . . . . ?
C10 C11 C12 C13 -1.1(6) . . . . ?
O1 C12 C13 C14 -178.4(4) . . . . ?
C11 C12 C13 C14 1.2(6) . . . . ?
C12 C13 C14 C9 -0.3(6) . . . . ?
C10 C9 C14 C13 -0.7(6) . . . . ?
C8 C9 C14 C13 179.2(4) . . . . ?

_refine_diff_density_max         0.305
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.058


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexanes/dichloromethane'
