# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_jus1705
_database_code_depnum_ccdc_archive 'CCDC 2047366'
loop_
_audit_author_name
_audit_author_address
'Michael Ferguson'
;University of Alberta
Canada
;
_audit_update_record             
;
2020-11-30 deposited with the CCDC.	2021-08-31 downloaded from the CCDC.
;

_vrf_PLAT094_jus1705             
;
RESPONSE: The large residual peak very close to the iodine atom
is most likely an artifact of unresolved crystal twinning due
to a small degree of crystal splitting.  One major component
and numerous minor components were observed when reflections
were harvested from the raw data frames for unit cell
determination.  The minor components showed little intensity
during data integration, and the final model showed no
improvement (with respect to this large residual peak) when
refined with data resulting from the multi-component
integration.
;

_vrf_PLAT971_jus1705             
;
RESPONSE: See above response to the PLAT094 alert.  The residual
peak is about 1 Angstrom away from the iodine atom, and has no
chemical significance (e.g. it is not due to cocrystallized
solvent or another functional group attached to the molecule
of interest).
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
2-(4-chlorophenyl)-7-iodo-5-methyl-3-phenyl-1-benzofuran
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H14 Cl I O'
_chemical_formula_sum            'C21 H14 Cl I O'
_chemical_formula_weight         444.67

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'
O O 0.0106 0.0060 '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                   8.1585(3)
_cell_length_b                   10.0268(4)
_cell_length_c                   11.7398(5)
_cell_angle_alpha                82.2199(4)
_cell_angle_beta                 69.7716(4)
_cell_angle_gamma                70.2331(4)
_cell_volume                     847.84(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    9922
_cell_measurement_theta_min      2.16
_cell_measurement_theta_max      28.79

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.742
_exptl_crystal_F_000             436
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.338
_exptl_crystal_size_mid          0.127
_exptl_crystal_size_min          0.111
_exptl_absorpt_coefficient_mu    2.050
_shelx_estimated_absorpt_T_min   0.544
_shelx_estimated_absorpt_T_max   0.804
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.0125
_exptl_absorpt_correction_T_max  0.0365
_exptl_absorpt_process_details   'SADABS 2016/2 (Krause et al., 2015)'
_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            8279
_diffrn_reflns_av_unetI/netI     0.0138
_diffrn_reflns_av_R_equivalents  0.0088
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.849
_diffrn_reflns_theta_max         29.066
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.937
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.937
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.937
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4253
_reflns_number_gt                4008
_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    'DIRDIF-2008 (Beurskens et al., 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0555P)²+0.8241P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4253
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0353
_refine_ls_R_factor_gt           0.0338
_refine_ls_wR_factor_ref         0.0944
_refine_ls_wR_factor_gt          0.0929
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
I I -0.16274(3) 1.01251(2) 0.38126(2) 0.04528(9) Uani 1 1 d . . . . .
Cl Cl 0.45284(12) 0.31982(8) 0.82656(7) 0.04725(17) Uani 1 1 d . . . . .
O O 0.0996(3) 0.67582(19) 0.40136(17) 0.0340(4) Uani 1 1 d . . . . .
C1 C 0.1987(3) 0.5312(3) 0.3946(2) 0.0326(5) Uani 1 1 d . . . . .
C2 C 0.2207(3) 0.4777(3) 0.2874(2) 0.0325(5) Uani 1 1 d . . . . .
C3 C 0.1325(3) 0.5952(3) 0.2200(2) 0.0328(5) Uani 1 1 d . . . . .
C4 C 0.1058(4) 0.6091(3) 0.1072(2) 0.0350(5) Uani 1 1 d . . . . .
H4 H 0.1533 0.5298 0.0561 0.042 Uiso 1 1 calc R U . . .
C5 C 0.0076(4) 0.7423(3) 0.0707(2) 0.0361(5) Uani 1 1 d . . . . .
C6 C -0.0619(4) 0.8572(3) 0.1483(2) 0.0360(5) Uani 1 1 d . . . . .
H6 H -0.1270 0.9473 0.1226 0.043 Uiso 1 1 calc R U . . .
C7 C -0.0389(4) 0.8439(3) 0.2617(2) 0.0339(5) Uani 1 1 d . . . . .
C8 C 0.0604(3) 0.7121(3) 0.2949(2) 0.0321(5) Uani 1 1 d . . . . .
C9 C 0.2623(3) 0.4759(3) 0.4994(2) 0.0317(5) Uani 1 1 d . . . . .
C10 C 0.2462(4) 0.5707(3) 0.5825(3) 0.0372(5) Uani 1 1 d . . . . .
H10 H 0.1927 0.6695 0.5705 0.045 Uiso 1 1 calc R U . . .
C11 C 0.3065(4) 0.5239(3) 0.6818(3) 0.0394(5) Uani 1 1 d . . . . .
H11 H 0.2972 0.5897 0.7366 0.047 Uiso 1 1 calc R U . . .
C12 C 0.3806(4) 0.3798(3) 0.7000(2) 0.0359(5) Uani 1 1 d . . . . .
C13 C 0.4003(4) 0.2823(3) 0.6191(3) 0.0398(6) Uani 1 1 d . . . . .
H13 H 0.4535 0.1837 0.6319 0.048 Uiso 1 1 calc R U . . .
C14 C 0.3412(4) 0.3309(3) 0.5189(3) 0.0385(5) Uani 1 1 d . . . . .
H14 H 0.3544 0.2649 0.4629 0.046 Uiso 1 1 calc R U . . .
C15 C 0.3167(3) 0.3325(3) 0.2393(2) 0.0325(5) Uani 1 1 d . . . . .
C16 C 0.2530(4) 0.2188(3) 0.2925(3) 0.0367(5) Uani 1 1 d . . . . .
H16 H 0.1489 0.2327 0.3640 0.044 Uiso 1 1 calc R U . . .
C17 C 0.3407(4) 0.0852(3) 0.2418(3) 0.0390(5) Uani 1 1 d . . . . .
H17 H 0.2963 0.0085 0.2791 0.047 Uiso 1 1 calc R U . . .
C18 C 0.4917(4) 0.0628(3) 0.1376(3) 0.0371(5) Uani 1 1 d . . . . .
H18 H 0.5510 -0.0287 0.1033 0.045 Uiso 1 1 calc R U . . .
C19 C 0.5566(4) 0.1767(3) 0.0828(2) 0.0387(5) Uani 1 1 d . . . . .
H19 H 0.6600 0.1627 0.0109 0.046 Uiso 1 1 calc R U . . .
C20 C 0.4691(4) 0.3100(3) 0.1339(2) 0.0361(5) Uani 1 1 d . . . . .
H20 H 0.5136 0.3867 0.0967 0.043 Uiso 1 1 calc R U . . .
C21 C -0.0254(5) 0.7632(4) -0.0501(3) 0.0458(6) Uani 1 1 d . . . . .
H21A H -0.1452 0.8346 -0.0427 0.055 Uiso 1 1 calc R U . . .
H21B H -0.0241 0.6734 -0.0750 0.055 Uiso 1 1 calc R U . . .
H21C H 0.0716 0.7953 -0.1111 0.055 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
I C7 2.087(3) . ?
Cl C12 1.744(3) . ?
O C8 1.368(3) . ?
O C1 1.399(3) . ?
C1 C2 1.366(4) . ?
C1 C9 1.467(3) . ?
C2 C3 1.450(3) . ?
C2 C15 1.482(3) . ?
C3 C8 1.396(4) . ?
C3 C4 1.396(4) . ?
C4 C5 1.402(4) . ?
C5 C6 1.402(4) . ?
C5 C21 1.508(4) . ?
C6 C7 1.389(4) . ?
C7 C8 1.382(3) . ?
C9 C10 1.397(4) . ?
C9 C14 1.399(4) . ?
C10 C11 1.384(4) . ?
C11 C12 1.383(4) . ?
C12 C13 1.388(4) . ?
C13 C14 1.390(4) . ?
C15 C16 1.394(4) . ?
C15 C20 1.396(4) . ?
C16 C17 1.391(4) . ?
C17 C18 1.382(4) . ?
C18 C19 1.405(4) . ?
C19 C20 1.390(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
C8 O C1 106.08(19) . . ?
C2 C1 O 111.0(2) . . ?
C2 C1 C9 135.5(2) . . ?
O C1 C9 113.4(2) . . ?
C1 C2 C3 106.3(2) . . ?
C1 C2 C15 130.5(2) . . ?
C3 C2 C15 123.1(2) . . ?
C8 C3 C4 120.1(2) . . ?
C8 C3 C2 105.6(2) . . ?
C4 C3 C2 134.2(2) . . ?
C3 C4 C5 118.8(2) . . ?
C6 C5 C4 119.3(2) . . ?
C6 C5 C21 119.7(2) . . ?
C4 C5 C21 121.0(3) . . ?
C7 C6 C5 122.3(2) . . ?
C8 C7 C6 117.3(2) . . ?
C8 C7 I 121.20(19) . . ?
C6 C7 I 121.41(19) . . ?
O C8 C7 126.9(2) . . ?
O C8 C3 110.9(2) . . ?
C7 C8 C3 122.1(2) . . ?
C10 C9 C14 118.3(2) . . ?
C10 C9 C1 119.2(2) . . ?
C14 C9 C1 122.5(2) . . ?
C11 C10 C9 121.4(3) . . ?
C12 C11 C10 119.0(3) . . ?
C11 C12 C13 121.4(2) . . ?
C11 C12 Cl 119.2(2) . . ?
C13 C12 Cl 119.4(2) . . ?
C12 C13 C14 119.0(3) . . ?
C13 C14 C9 120.9(3) . . ?
C16 C15 C20 118.8(2) . . ?
C16 C15 C2 121.7(2) . . ?
C20 C15 C2 119.3(2) . . ?
C17 C16 C15 120.4(3) . . ?
C18 C17 C16 120.7(3) . . ?
C17 C18 C19 119.3(2) . . ?
C20 C19 C18 119.8(3) . . ?
C19 C20 C15 120.8(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
C8 O C1 C2 -0.3(3) . . . . ?
C8 O C1 C9 176.5(2) . . . . ?
O C1 C2 C3 0.8(3) . . . . ?
C9 C1 C2 C3 -175.0(3) . . . . ?
O C1 C2 C15 179.2(2) . . . . ?
C9 C1 C2 C15 3.4(5) . . . . ?
C1 C2 C3 C8 -0.9(3) . . . . ?
C15 C2 C3 C8 -179.5(2) . . . . ?
C1 C2 C3 C4 -179.0(3) . . . . ?
C15 C2 C3 C4 2.4(4) . . . . ?
C8 C3 C4 C5 0.7(4) . . . . ?
C2 C3 C4 C5 178.5(3) . . . . ?
C3 C4 C5 C6 -0.4(4) . . . . ?
C3 C4 C5 C21 -179.9(3) . . . . ?
C4 C5 C6 C7 -0.7(4) . . . . ?
C21 C5 C6 C7 178.8(3) . . . . ?
C5 C6 C7 C8 1.6(4) . . . . ?
C5 C6 C7 I -174.8(2) . . . . ?
C1 O C8 C7 178.6(3) . . . . ?
C1 O C8 C3 -0.3(3) . . . . ?
C6 C7 C8 O 179.9(2) . . . . ?
I C7 C8 O -3.7(4) . . . . ?
C6 C7 C8 C3 -1.4(4) . . . . ?
I C7 C8 C3 175.02(19) . . . . ?
C4 C3 C8 O 179.2(2) . . . . ?
C2 C3 C8 O 0.8(3) . . . . ?
C4 C3 C8 C7 0.2(4) . . . . ?
C2 C3 C8 C7 -178.2(2) . . . . ?
C2 C1 C9 C10 165.7(3) . . . . ?
O C1 C9 C10 -10.0(3) . . . . ?
C2 C1 C9 C14 -13.4(5) . . . . ?
O C1 C9 C14 170.9(2) . . . . ?
C14 C9 C10 C11 0.1(4) . . . . ?
C1 C9 C10 C11 -179.1(3) . . . . ?
C9 C10 C11 C12 -1.4(4) . . . . ?
C10 C11 C12 C13 1.9(4) . . . . ?
C10 C11 C12 Cl -178.8(2) . . . . ?
C11 C12 C13 C14 -1.2(4) . . . . ?
Cl C12 C13 C14 179.5(2) . . . . ?
C12 C13 C14 C9 -0.2(4) . . . . ?
C10 C9 C14 C13 0.7(4) . . . . ?
C1 C9 C14 C13 179.8(3) . . . . ?
C1 C2 C15 C16 67.0(4) . . . . ?
C3 C2 C15 C16 -114.8(3) . . . . ?
C1 C2 C15 C20 -116.6(3) . . . . ?
C3 C2 C15 C20 61.5(3) . . . . ?
C20 C15 C16 C17 0.4(4) . . . . ?
C2 C15 C16 C17 176.8(2) . . . . ?
C15 C16 C17 C18 -0.3(4) . . . . ?
C16 C17 C18 C19 0.0(4) . . . . ?
C17 C18 C19 C20 0.2(4) . . . . ?
C18 C19 C20 C15 -0.1(4) . . . . ?
C16 C15 C20 C19 -0.2(4) . . . . ?
C2 C15 C20 C19 -176.6(2) . . . . ?

_refine_diff_density_max         3.038
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.100


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: chloroform'
####################################################################### 
# 
# 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_jus1802
_database_code_depnum_ccdc_archive 'CCDC 2047367'
loop_
_audit_author_name
_audit_author_address
'Michael Ferguson'
;University of Alberta
Canada
;
_audit_update_record             
;
2020-11-30 deposited with the CCDC.	2021-08-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        
2-(4-chlorophenyl)-7-iodo-3-phenyl-1-benzofuran
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H12 Cl I O'
_chemical_formula_sum            'C20 H12 Cl I O'
_chemical_formula_weight         430.65

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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                   9.244(2)
_cell_length_b                   9.988(3)
_cell_length_c                   10.515(3)
_cell_angle_alpha                86.607(3)
_cell_angle_beta                 65.448(3)
_cell_angle_gamma                70.670(3)
_cell_volume                     829.8(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    6231
_cell_measurement_theta_min      2.17
_cell_measurement_theta_max      27.62

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.724
_exptl_crystal_F_000             420
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.235
_exptl_crystal_size_mid          0.194
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    2.092
_shelx_estimated_absorpt_T_min   0.639
_shelx_estimated_absorpt_T_max   0.921
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.7307
_exptl_absorpt_correction_T_max  0.9393
_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      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            7499
_diffrn_reflns_av_unetI/netI     0.0221
_diffrn_reflns_av_R_equivalents  0.0149
_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       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.138
_diffrn_reflns_theta_max         27.634
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3843
_reflns_number_gt                3365
_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)+(0.0329P)²+0.3747P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3843
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0318
_refine_ls_R_factor_gt           0.0265
_refine_ls_wR_factor_ref         0.0676
_refine_ls_wR_factor_gt          0.0640
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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 0.79344(2) -0.01350(2) 0.34954(2) 0.04862(8) Uani 1 1 d . . . . .
Cl1 Cl -0.27026(7) 0.67509(6) 0.82007(6) 0.03918(14) Uani 1 1 d . . . . .
O1 O 0.52940(19) 0.31735(15) 0.37816(16) 0.0291(3) Uani 1 1 d . . . . .
C1 C 0.4391(3) 0.4592(2) 0.3730(2) 0.0267(4) Uani 1 1 d . . . . .
C2 C 0.5323(3) 0.5162(2) 0.2616(2) 0.0274(4) Uani 1 1 d . . . . .
C3 C 0.6931(3) 0.4057(2) 0.1897(2) 0.0275(4) Uani 1 1 d . . . . .
C4 C 0.8424(3) 0.3965(3) 0.0697(2) 0.0330(5) Uani 1 1 d . . . . .
H4 H 0.852628 0.476011 0.016856 0.040 Uiso 1 1 calc R U . . .
C5 C 0.9737(3) 0.2671(3) 0.0317(3) 0.0368(5) Uani 1 1 d . . . . .
H5 H 1.075609 0.258576 -0.048673 0.044 Uiso 1 1 calc R U . . .
C6 C 0.9607(3) 0.1487(3) 0.1081(3) 0.0360(5) Uani 1 1 d . . . . .
H6 H 1.053036 0.061524 0.078350 0.043 Uiso 1 1 calc R U . . .
C7 C 0.8149(3) 0.1571(2) 0.2265(2) 0.0326(5) Uani 1 1 d . . . . .
C8 C 0.6826(3) 0.2866(2) 0.2648(2) 0.0283(4) Uani 1 1 d . . . . .
C9 C 0.2664(3) 0.5130(2) 0.4836(2) 0.0271(4) Uani 1 1 d . . . . .
C10 C 0.1913(3) 0.4185(2) 0.5657(2) 0.0300(4) Uani 1 1 d . . . . .
H10 H 0.253679 0.319351 0.550268 0.036 Uiso 1 1 calc R U . . .
C11 C 0.0271(3) 0.4674(2) 0.6693(2) 0.0324(5) Uani 1 1 d . . . . .
H11 H -0.022786 0.402387 0.724557 0.039 Uiso 1 1 calc R U . . .
C12 C -0.0633(3) 0.6122(2) 0.6910(2) 0.0301(4) Uani 1 1 d . . . . .
C13 C 0.0079(3) 0.7085(2) 0.6113(2) 0.0311(5) Uani 1 1 d . . . . .
H13 H -0.055278 0.807474 0.627120 0.037 Uiso 1 1 calc R U . . .
C14 C 0.1720(3) 0.6590(2) 0.5086(2) 0.0304(5) Uani 1 1 d . . . . .
H14 H 0.221265 0.724729 0.454201 0.036 Uiso 1 1 calc R U . . .
C15 C 0.4773(3) 0.6594(2) 0.2136(2) 0.0267(4) Uani 1 1 d . . . . .
C16 C 0.3862(3) 0.6816(2) 0.1326(2) 0.0311(5) Uani 1 1 d . . . . .
H16 H 0.361866 0.604755 0.106810 0.037 Uiso 1 1 calc R U . . .
C17 C 0.3306(3) 0.8156(2) 0.0891(3) 0.0350(5) Uani 1 1 d . . . . .
H17 H 0.268378 0.829803 0.033845 0.042 Uiso 1 1 calc R U . . .
C18 C 0.3652(3) 0.9283(2) 0.1257(3) 0.0372(5) Uani 1 1 d . . . . .
H18 H 0.326260 1.019935 0.096522 0.045 Uiso 1 1 calc R U . . .
C19 C 0.4568(4) 0.9065(3) 0.2050(3) 0.0427(6) Uani 1 1 d . . . . .
H19 H 0.480702 0.983730 0.230433 0.051 Uiso 1 1 calc R U . . .
C20 C 0.5144(3) 0.7729(3) 0.2481(3) 0.0386(5) Uani 1 1 d . . . . .
H20 H 0.579176 0.758781 0.301169 0.046 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 C7 2.090(2) . ?
Cl1 C12 1.744(2) . ?
O1 C8 1.369(3) . ?
O1 C1 1.397(2) . ?
C1 C2 1.359(3) . ?
C1 C9 1.467(3) . ?
C2 C3 1.442(3) . ?
C2 C15 1.485(3) . ?
C3 C8 1.397(3) . ?
C3 C4 1.409(3) . ?
C4 C5 1.387(3) . ?
C5 C6 1.400(4) . ?
C6 C7 1.384(3) . ?
C7 C8 1.391(3) . ?
C9 C10 1.399(3) . ?
C9 C14 1.403(3) . ?
C10 C11 1.389(3) . ?
C11 C12 1.387(3) . ?
C12 C13 1.388(3) . ?
C13 C14 1.384(3) . ?
C15 C16 1.390(3) . ?
C15 C20 1.394(3) . ?
C16 C17 1.390(3) . ?
C17 C18 1.382(3) . ?
C18 C19 1.379(4) . ?
C19 C20 1.389(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
C8 O1 C1 105.83(16) . . ?
C2 C1 O1 111.13(18) . . ?
C2 C1 C9 133.95(19) . . ?
O1 C1 C9 114.90(18) . . ?
C1 C2 C3 106.62(18) . . ?
C1 C2 C15 127.57(19) . . ?
C3 C2 C15 125.60(19) . . ?
C8 C3 C4 119.6(2) . . ?
C8 C3 C2 105.60(19) . . ?
C4 C3 C2 134.8(2) . . ?
C5 C4 C3 117.6(2) . . ?
C4 C5 C6 122.0(2) . . ?
C7 C6 C5 120.8(2) . . ?
C6 C7 C8 117.4(2) . . ?
C6 C7 I1 122.23(17) . . ?
C8 C7 I1 120.32(17) . . ?
O1 C8 C7 126.6(2) . . ?
O1 C8 C3 110.80(18) . . ?
C7 C8 C3 122.6(2) . . ?
C10 C9 C14 118.5(2) . . ?
C10 C9 C1 120.22(19) . . ?
C14 C9 C1 121.30(19) . . ?
C11 C10 C9 121.0(2) . . ?
C12 C11 C10 119.2(2) . . ?
C11 C12 C13 121.1(2) . . ?
C11 C12 Cl1 119.73(17) . . ?
C13 C12 Cl1 119.20(17) . . ?
C14 C13 C12 119.4(2) . . ?
C13 C14 C9 120.9(2) . . ?
C16 C15 C20 118.9(2) . . ?
C16 C15 C2 119.56(19) . . ?
C20 C15 C2 121.5(2) . . ?
C17 C16 C15 120.4(2) . . ?
C18 C17 C16 120.5(2) . . ?
C19 C18 C17 119.4(2) . . ?
C18 C19 C20 120.7(2) . . ?
C19 C20 C15 120.1(2) . . ?

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
C8 O1 C1 C2 -0.6(2) . . . . ?
C8 O1 C1 C9 177.81(17) . . . . ?
O1 C1 C2 C3 -0.1(2) . . . . ?
C9 C1 C2 C3 -178.2(2) . . . . ?
O1 C1 C2 C15 174.78(19) . . . . ?
C9 C1 C2 C15 -3.3(4) . . . . ?
C1 C2 C3 C8 0.8(2) . . . . ?
C15 C2 C3 C8 -174.21(19) . . . . ?
C1 C2 C3 C4 -179.8(2) . . . . ?
C15 C2 C3 C4 5.2(4) . . . . ?
C8 C3 C4 C5 0.0(3) . . . . ?
C2 C3 C4 C5 -179.4(2) . . . . ?
C3 C4 C5 C6 0.2(3) . . . . ?
C4 C5 C6 C7 -0.6(3) . . . . ?
C5 C6 C7 C8 0.7(3) . . . . ?
C5 C6 C7 I1 -177.03(17) . . . . ?
C1 O1 C8 C7 -179.9(2) . . . . ?
C1 O1 C8 C3 1.2(2) . . . . ?
C6 C7 C8 O1 -179.41(19) . . . . ?
I1 C7 C8 O1 -1.6(3) . . . . ?
C6 C7 C8 C3 -0.6(3) . . . . ?
I1 C7 C8 C3 177.24(15) . . . . ?
C4 C3 C8 O1 179.21(18) . . . . ?
C2 C3 C8 O1 -1.2(2) . . . . ?
C4 C3 C8 C7 0.2(3) . . . . ?
C2 C3 C8 C7 179.8(2) . . . . ?
C2 C1 C9 C10 164.8(2) . . . . ?
O1 C1 C9 C10 -13.2(3) . . . . ?
C2 C1 C9 C14 -14.2(4) . . . . ?
O1 C1 C9 C14 167.77(18) . . . . ?
C14 C9 C10 C11 0.2(3) . . . . ?
C1 C9 C10 C11 -178.9(2) . . . . ?
C9 C10 C11 C12 0.1(3) . . . . ?
C10 C11 C12 C13 -0.1(3) . . . . ?
C10 C11 C12 Cl1 179.61(17) . . . . ?
C11 C12 C13 C14 -0.1(3) . . . . ?
Cl1 C12 C13 C14 -179.83(17) . . . . ?
C12 C13 C14 C9 0.3(3) . . . . ?
C10 C9 C14 C13 -0.4(3) . . . . ?
C1 C9 C14 C13 178.7(2) . . . . ?
C1 C2 C15 C16 -81.0(3) . . . . ?
C3 C2 C15 C16 93.0(3) . . . . ?
C1 C2 C15 C20 98.9(3) . . . . ?
C3 C2 C15 C20 -87.1(3) . . . . ?
C20 C15 C16 C17 -1.2(3) . . . . ?
C2 C15 C16 C17 178.7(2) . . . . ?
C15 C16 C17 C18 0.1(4) . . . . ?
C16 C17 C18 C19 0.5(4) . . . . ?
C17 C18 C19 C20 0.1(4) . . . . ?
C18 C19 C20 C15 -1.2(4) . . . . ?
C16 C15 C20 C19 1.7(4) . . . . ?
C2 C15 C20 C19 -178.1(2) . . . . ?

_refine_diff_density_max         0.636
_refine_diff_density_min         -0.727
_refine_diff_density_rms         0.069


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane'
